EP3492563A1 - Refrigerating machine oil - Google Patents
Refrigerating machine oil Download PDFInfo
- Publication number
- EP3492563A1 EP3492563A1 EP17834535.1A EP17834535A EP3492563A1 EP 3492563 A1 EP3492563 A1 EP 3492563A1 EP 17834535 A EP17834535 A EP 17834535A EP 3492563 A1 EP3492563 A1 EP 3492563A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- group
- carbon atoms
- refrigerating machine
- acid
- less
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000010721 machine oil Substances 0.000 title claims abstract description 66
- 150000001875 compounds Chemical class 0.000 claims abstract description 70
- 239000002199 base oil Substances 0.000 claims abstract description 51
- 230000001050 lubricating effect Effects 0.000 claims abstract description 16
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 7
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 4
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 4
- -1 glycidyl ester Chemical class 0.000 claims description 52
- 239000004593 Epoxy Substances 0.000 claims description 46
- 150000002148 esters Chemical class 0.000 claims description 32
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 28
- 229930195729 fatty acid Natural products 0.000 claims description 28
- 239000000194 fatty acid Substances 0.000 claims description 28
- 150000004665 fatty acids Chemical class 0.000 claims description 28
- 239000003921 oil Substances 0.000 claims description 14
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
- 239000001301 oxygen Substances 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 125000002723 alicyclic group Chemical group 0.000 claims description 9
- 239000010773 plant oil Substances 0.000 claims description 5
- 150000002170 ethers Chemical class 0.000 claims description 4
- 150000002924 oxiranes Chemical class 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 96
- 239000003507 refrigerant Substances 0.000 description 74
- 150000002430 hydrocarbons Chemical group 0.000 description 59
- 125000000217 alkyl group Chemical group 0.000 description 51
- 239000000203 mixture Substances 0.000 description 46
- 229920001289 polyvinyl ether Polymers 0.000 description 27
- 229920001515 polyalkylene glycol Polymers 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 20
- 150000004996 alkyl benzenes Chemical class 0.000 description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 18
- 239000004215 Carbon black (E152) Substances 0.000 description 16
- 229930195733 hydrocarbon Natural products 0.000 description 16
- 150000005846 sugar alcohols Polymers 0.000 description 16
- 239000002253 acid Substances 0.000 description 14
- 235000019198 oils Nutrition 0.000 description 13
- 230000000052 comparative effect Effects 0.000 description 11
- 229920001577 copolymer Polymers 0.000 description 11
- 229920005862 polyol Polymers 0.000 description 11
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 9
- 239000000654 additive Substances 0.000 description 8
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- OILUAKBAMVLXGF-UHFFFAOYSA-N 3,5,5-trimethyl-hexanoic acid Chemical compound OC(=O)CC(C)CC(C)(C)C OILUAKBAMVLXGF-UHFFFAOYSA-N 0.000 description 7
- 125000002252 acyl group Chemical group 0.000 description 7
- 150000001298 alcohols Chemical class 0.000 description 7
- 125000002947 alkylene group Chemical group 0.000 description 7
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 7
- 239000000178 monomer Substances 0.000 description 7
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 7
- 150000007519 polyprotic acids Polymers 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 6
- 229910019142 PO4 Inorganic materials 0.000 description 6
- 239000003963 antioxidant agent Substances 0.000 description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 6
- 239000010452 phosphate Substances 0.000 description 6
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 6
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 239000001361 adipic acid Substances 0.000 description 5
- 235000011037 adipic acid Nutrition 0.000 description 5
- 230000003078 antioxidant effect Effects 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 5
- 239000011630 iodine Substances 0.000 description 5
- 229910052740 iodine Inorganic materials 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 125000005702 oxyalkylene group Chemical group 0.000 description 5
- 150000002978 peroxides Chemical class 0.000 description 5
- 229920013639 polyalphaolefin Polymers 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 4
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 229920001400 block copolymer Polymers 0.000 description 4
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000012530 fluid Substances 0.000 description 4
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 4
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 4
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 4
- 238000005461 lubrication Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 4
- 125000006353 oxyethylene group Chemical group 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical class [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 4
- 229920001451 polypropylene glycol Polymers 0.000 description 4
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 4
- 229920005604 random copolymer Polymers 0.000 description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
- CDOOAUSHHFGWSA-OWOJBTEDSA-N (e)-1,3,3,3-tetrafluoroprop-1-ene Chemical compound F\C=C\C(F)(F)F CDOOAUSHHFGWSA-OWOJBTEDSA-N 0.000 description 3
- NPNPZTNLOVBDOC-UHFFFAOYSA-N 1,1-difluoroethane Chemical compound CC(F)F NPNPZTNLOVBDOC-UHFFFAOYSA-N 0.000 description 3
- FJNCXZZQNBKEJT-UHFFFAOYSA-N 8beta-hydroxymarrubiin Natural products O1C(=O)C2(C)CCCC3(C)C2C1CC(C)(O)C3(O)CCC=1C=COC=1 FJNCXZZQNBKEJT-UHFFFAOYSA-N 0.000 description 3
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 238000011088 calibration curve Methods 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- QQWAKSKPSOFJFF-UHFFFAOYSA-N oxiran-2-ylmethyl 2,2-dimethyloctanoate Chemical compound CCCCCCC(C)(C)C(=O)OCC1CO1 QQWAKSKPSOFJFF-UHFFFAOYSA-N 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
- 238000007670 refining Methods 0.000 description 3
- 238000013112 stability test Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- FYIRUPZTYPILDH-UHFFFAOYSA-N 1,1,1,2,3,3-hexafluoropropane Chemical compound FC(F)C(F)C(F)(F)F FYIRUPZTYPILDH-UHFFFAOYSA-N 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 description 2
- VJGCZWVJDRIHNC-UHFFFAOYSA-N 1-fluoroprop-1-ene Chemical compound CC=CF VJGCZWVJDRIHNC-UHFFFAOYSA-N 0.000 description 2
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- BBBUAWSVILPJLL-UHFFFAOYSA-N 2-(2-ethylhexoxymethyl)oxirane Chemical compound CCCCC(CC)COCC1CO1 BBBUAWSVILPJLL-UHFFFAOYSA-N 0.000 description 2
- NKBWMBRPILTCRD-UHFFFAOYSA-N 2-Methylheptanoic acid Chemical compound CCCCCC(C)C(O)=O NKBWMBRPILTCRD-UHFFFAOYSA-N 0.000 description 2
- OVBFMEVBMNZIBR-UHFFFAOYSA-N 2-methylvaleric acid Chemical compound CCCC(C)C(O)=O OVBFMEVBMNZIBR-UHFFFAOYSA-N 0.000 description 2
- BODRLKRKPXBDBN-UHFFFAOYSA-N 3,5,5-Trimethyl-1-hexanol Chemical compound OCCC(C)CC(C)(C)C BODRLKRKPXBDBN-UHFFFAOYSA-N 0.000 description 2
- AWQSAIIDOMEEOD-UHFFFAOYSA-N 5,5-Dimethyl-4-(3-oxobutyl)dihydro-2(3H)-furanone Chemical compound CC(=O)CCC1CC(=O)OC1(C)C AWQSAIIDOMEEOD-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- 229920001774 Perfluoroether Polymers 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 2
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- RWRIWBAIICGTTQ-UHFFFAOYSA-N difluoromethane Chemical compound FCF RWRIWBAIICGTTQ-UHFFFAOYSA-N 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- CKDDRHZIAZRDBW-UHFFFAOYSA-N henicosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCC(O)=O CKDDRHZIAZRDBW-UHFFFAOYSA-N 0.000 description 2
- KEMQGTRYUADPNZ-UHFFFAOYSA-N heptadecanoic acid Chemical compound CCCCCCCCCCCCCCCCC(O)=O KEMQGTRYUADPNZ-UHFFFAOYSA-N 0.000 description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 239000001282 iso-butane Substances 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- ISYWECDDZWTKFF-UHFFFAOYSA-N nonadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCCC(O)=O ISYWECDDZWTKFF-UHFFFAOYSA-N 0.000 description 2
- 125000001196 nonadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- UJMWVICAENGCRF-UHFFFAOYSA-N oxygen difluoride Chemical compound FOF UJMWVICAENGCRF-UHFFFAOYSA-N 0.000 description 2
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- MSSNHSVIGIHOJA-UHFFFAOYSA-N pentafluoropropane Chemical compound FC(F)CC(F)(F)F MSSNHSVIGIHOJA-UHFFFAOYSA-N 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 150000003014 phosphoric acid esters Chemical class 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N sec-butylidene Natural products CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 2
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 2
- 235000019345 sodium thiosulphate Nutrition 0.000 description 2
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- XEZVDURJDFGERA-UHFFFAOYSA-N tricosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCC(O)=O XEZVDURJDFGERA-UHFFFAOYSA-N 0.000 description 2
- SZHOJFHSIKHZHA-UHFFFAOYSA-N tridecanoic acid Chemical compound CCCCCCCCCCCCC(O)=O SZHOJFHSIKHZHA-UHFFFAOYSA-N 0.000 description 2
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 2
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000003643 water by type Substances 0.000 description 2
- 239000004711 α-olefin Substances 0.000 description 2
- GJEZBVHHZQAEDB-SYDPRGILSA-N (1s,5r)-6-oxabicyclo[3.1.0]hexane Chemical compound C1CC[C@H]2O[C@H]21 GJEZBVHHZQAEDB-SYDPRGILSA-N 0.000 description 1
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical compound O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 description 1
- DMUPYMORYHFFCT-UPHRSURJSA-N (z)-1,2,3,3,3-pentafluoroprop-1-ene Chemical compound F\C=C(/F)C(F)(F)F DMUPYMORYHFFCT-UPHRSURJSA-N 0.000 description 1
- YFMFNYKEUDLDTL-UHFFFAOYSA-N 1,1,1,2,3,3,3-heptafluoropropane Chemical compound FC(F)(F)C(F)C(F)(F)F YFMFNYKEUDLDTL-UHFFFAOYSA-N 0.000 description 1
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 description 1
- INEMUVRCEAELBK-UHFFFAOYSA-N 1,1,1,2-tetrafluoropropane Chemical compound CC(F)C(F)(F)F INEMUVRCEAELBK-UHFFFAOYSA-N 0.000 description 1
- NSGXIBWMJZWTPY-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropane Chemical compound FC(F)(F)CC(F)(F)F NSGXIBWMJZWTPY-UHFFFAOYSA-N 0.000 description 1
- WZLFPVPRZGTCKP-UHFFFAOYSA-N 1,1,1,3,3-pentafluorobutane Chemical compound CC(F)(F)CC(F)(F)F WZLFPVPRZGTCKP-UHFFFAOYSA-N 0.000 description 1
- PFFGXVGPSGJOBV-UHFFFAOYSA-N 1,1,1,3-tetrafluoropropane Chemical compound FCCC(F)(F)F PFFGXVGPSGJOBV-UHFFFAOYSA-N 0.000 description 1
- UJPMYEOUBPIPHQ-UHFFFAOYSA-N 1,1,1-trifluoroethane Chemical compound CC(F)(F)F UJPMYEOUBPIPHQ-UHFFFAOYSA-N 0.000 description 1
- WXGNWUVNYMJENI-UHFFFAOYSA-N 1,1,2,2-tetrafluoroethane Chemical compound FC(F)C(F)F WXGNWUVNYMJENI-UHFFFAOYSA-N 0.000 description 1
- AYNJDIUGIVKMNZ-UHFFFAOYSA-N 1,1,2,3-tetrafluoropropane Chemical compound FCC(F)C(F)F AYNJDIUGIVKMNZ-UHFFFAOYSA-N 0.000 description 1
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 1
- DSZTYVZOIUIIGA-UHFFFAOYSA-N 1,2-Epoxyhexadecane Chemical compound CCCCCCCCCCCCCCC1CO1 DSZTYVZOIUIIGA-UHFFFAOYSA-N 0.000 description 1
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 1
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 1
- JQKFBWPNTWIPDH-UHFFFAOYSA-N 2,2-diethylpentane-1,3-diol Chemical compound CCC(O)C(CC)(CC)CO JQKFBWPNTWIPDH-UHFFFAOYSA-N 0.000 description 1
- HORQAOAYAYGIBM-UHFFFAOYSA-N 2,4-dinitrophenylhydrazine Chemical compound NNC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O HORQAOAYAYGIBM-UHFFFAOYSA-N 0.000 description 1
- NPKKFQUHBHQTSH-UHFFFAOYSA-N 2-(decoxymethyl)oxirane Chemical compound CCCCCCCCCCOCC1CO1 NPKKFQUHBHQTSH-UHFFFAOYSA-N 0.000 description 1
- VMSIYTPWZLSMOH-UHFFFAOYSA-N 2-(dodecoxymethyl)oxirane Chemical compound CCCCCCCCCCCCOCC1CO1 VMSIYTPWZLSMOH-UHFFFAOYSA-N 0.000 description 1
- SZSSMFVYZRQGIM-UHFFFAOYSA-N 2-(hydroxymethyl)-2-propylpropane-1,3-diol Chemical compound CCCC(CO)(CO)CO SZSSMFVYZRQGIM-UHFFFAOYSA-N 0.000 description 1
- NVKSMKFBUGBIGE-UHFFFAOYSA-N 2-(tetradecoxymethyl)oxirane Chemical compound CCCCCCCCCCCCCCOCC1CO1 NVKSMKFBUGBIGE-UHFFFAOYSA-N 0.000 description 1
- ZCZCZLVSKGCRTD-UHFFFAOYSA-N 2-(tridecoxymethyl)oxirane Chemical compound CCCCCCCCCCCCCOCC1CO1 ZCZCZLVSKGCRTD-UHFFFAOYSA-N 0.000 description 1
- HNJSJLKMMRCGKX-UHFFFAOYSA-N 2-(undecoxymethyl)oxirane Chemical compound CCCCCCCCCCCOCC1CO1 HNJSJLKMMRCGKX-UHFFFAOYSA-N 0.000 description 1
- WLAMNBDJUVNPJU-BYPYZUCNSA-N 2-Methylbutanoic acid Natural products CC[C@H](C)C(O)=O WLAMNBDJUVNPJU-BYPYZUCNSA-N 0.000 description 1
- WAPRZVXVTPSWEB-UHFFFAOYSA-N 2-[(2-butan-2-ylphenoxy)methyl]oxirane Chemical compound CCC(C)C1=CC=CC=C1OCC1OC1 WAPRZVXVTPSWEB-UHFFFAOYSA-N 0.000 description 1
- HJEORQYOUWYAMR-UHFFFAOYSA-N 2-[(2-butylphenoxy)methyl]oxirane Chemical compound CCCCC1=CC=CC=C1OCC1OC1 HJEORQYOUWYAMR-UHFFFAOYSA-N 0.000 description 1
- RRXIBRLPSOBLIQ-UHFFFAOYSA-N 2-[(2-decylphenoxy)methyl]oxirane Chemical compound CCCCCCCCCCC1=CC=CC=C1OCC1OC1 RRXIBRLPSOBLIQ-UHFFFAOYSA-N 0.000 description 1
- ABTAANTUIVCOTF-UHFFFAOYSA-N 2-[(2-heptylphenoxy)methyl]oxirane Chemical compound CCCCCCCC1=CC=CC=C1OCC1OC1 ABTAANTUIVCOTF-UHFFFAOYSA-N 0.000 description 1
- LEYWCVIABUVRSU-UHFFFAOYSA-N 2-[(2-hexylphenoxy)methyl]oxirane Chemical compound CCCCCCC1=CC=CC=C1OCC1OC1 LEYWCVIABUVRSU-UHFFFAOYSA-N 0.000 description 1
- WNISWKAEAPQCJQ-UHFFFAOYSA-N 2-[(2-nonylphenoxy)methyl]oxirane Chemical compound CCCCCCCCCC1=CC=CC=C1OCC1OC1 WNISWKAEAPQCJQ-UHFFFAOYSA-N 0.000 description 1
- UYBCNHLHWUHLOF-UHFFFAOYSA-N 2-[(2-pentylphenoxy)methyl]oxirane Chemical compound CCCCCC1=CC=CC=C1OCC1OC1 UYBCNHLHWUHLOF-UHFFFAOYSA-N 0.000 description 1
- HHRACYLRBOUBKM-UHFFFAOYSA-N 2-[(4-tert-butylphenoxy)methyl]oxirane Chemical compound C1=CC(C(C)(C)C)=CC=C1OCC1OC1 HHRACYLRBOUBKM-UHFFFAOYSA-N 0.000 description 1
- WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-UHFFFAOYSA-N 0.000 description 1
- AOBIOSPNXBMOAT-UHFFFAOYSA-N 2-[2-(oxiran-2-ylmethoxy)ethoxymethyl]oxirane Chemical compound C1OC1COCCOCC1CO1 AOBIOSPNXBMOAT-UHFFFAOYSA-N 0.000 description 1
- WTYYGFLRBWMFRY-UHFFFAOYSA-N 2-[6-(oxiran-2-ylmethoxy)hexoxymethyl]oxirane Chemical compound C1OC1COCCCCCCOCC1CO1 WTYYGFLRBWMFRY-UHFFFAOYSA-N 0.000 description 1
- KUAUJXBLDYVELT-UHFFFAOYSA-N 2-[[2,2-dimethyl-3-(oxiran-2-ylmethoxy)propoxy]methyl]oxirane Chemical compound C1OC1COCC(C)(C)COCC1CO1 KUAUJXBLDYVELT-UHFFFAOYSA-N 0.000 description 1
- PLDLPVSQYMQDBL-UHFFFAOYSA-N 2-[[3-(oxiran-2-ylmethoxy)-2,2-bis(oxiran-2-ylmethoxymethyl)propoxy]methyl]oxirane Chemical compound C1OC1COCC(COCC1OC1)(COCC1OC1)COCC1CO1 PLDLPVSQYMQDBL-UHFFFAOYSA-N 0.000 description 1
- WHNBDXQTMPYBAT-UHFFFAOYSA-N 2-butyloxirane Chemical compound CCCCC1CO1 WHNBDXQTMPYBAT-UHFFFAOYSA-N 0.000 description 1
- MPGABYXKKCLIRW-UHFFFAOYSA-N 2-decyloxirane Chemical compound CCCCCCCCCCC1CO1 MPGABYXKKCLIRW-UHFFFAOYSA-N 0.000 description 1
- IOHJQSFEAYDZGF-UHFFFAOYSA-N 2-dodecyloxirane Chemical compound CCCCCCCCCCCCC1CO1 IOHJQSFEAYDZGF-UHFFFAOYSA-N 0.000 description 1
- YXLHBXPGRDAQSH-UHFFFAOYSA-N 2-ethylhexadecanoic acid Chemical compound CCCCCCCCCCCCCCC(CC)C(O)=O YXLHBXPGRDAQSH-UHFFFAOYSA-N 0.000 description 1
- CEUXMUYHMURJFZ-UHFFFAOYSA-N 2-heptadecyloxirane Chemical compound CCCCCCCCCCCCCCCCCC1CO1 CEUXMUYHMURJFZ-UHFFFAOYSA-N 0.000 description 1
- GXOYTMXAKFMIRK-UHFFFAOYSA-N 2-heptyloxirane Chemical compound CCCCCCCC1CO1 GXOYTMXAKFMIRK-UHFFFAOYSA-N 0.000 description 1
- QBJWYMFTMJFGOL-UHFFFAOYSA-N 2-hexadecyloxirane Chemical compound CCCCCCCCCCCCCCCCC1CO1 QBJWYMFTMJFGOL-UHFFFAOYSA-N 0.000 description 1
- NJWSNNWLBMSXQR-UHFFFAOYSA-N 2-hexyloxirane Chemical compound CCCCCCC1CO1 NJWSNNWLBMSXQR-UHFFFAOYSA-N 0.000 description 1
- WLAMNBDJUVNPJU-UHFFFAOYSA-N 2-methylbutyric acid Chemical compound CCC(C)C(O)=O WLAMNBDJUVNPJU-UHFFFAOYSA-N 0.000 description 1
- CVKMFSAVYPAZTQ-UHFFFAOYSA-N 2-methylhexanoic acid Chemical compound CCCCC(C)C(O)=O CVKMFSAVYPAZTQ-UHFFFAOYSA-N 0.000 description 1
- QWGRWMMWNDWRQN-UHFFFAOYSA-N 2-methylpropane-1,3-diol Chemical compound OCC(C)CO QWGRWMMWNDWRQN-UHFFFAOYSA-N 0.000 description 1
- LXVAZSIZYQIZCR-UHFFFAOYSA-N 2-nonyloxirane Chemical compound CCCCCCCCCC1CO1 LXVAZSIZYQIZCR-UHFFFAOYSA-N 0.000 description 1
- BHZBVWCLMYQFQX-UHFFFAOYSA-N 2-octadecyloxirane Chemical compound CCCCCCCCCCCCCCCCCCC1CO1 BHZBVWCLMYQFQX-UHFFFAOYSA-N 0.000 description 1
- AAMHBRRZYSORSH-UHFFFAOYSA-N 2-octyloxirane Chemical compound CCCCCCCCC1CO1 AAMHBRRZYSORSH-UHFFFAOYSA-N 0.000 description 1
- XSNXNMMWBCZUSS-UHFFFAOYSA-N 2-pentadecyloxirane Chemical compound CCCCCCCCCCCCCCCC1CO1 XSNXNMMWBCZUSS-UHFFFAOYSA-N 0.000 description 1
- NMOFYYYCFRVWBK-UHFFFAOYSA-N 2-pentyloxirane Chemical compound CCCCCC1CO1 NMOFYYYCFRVWBK-UHFFFAOYSA-N 0.000 description 1
- SYURNNNQIFDVCA-UHFFFAOYSA-N 2-propyloxirane Chemical compound CCCC1CO1 SYURNNNQIFDVCA-UHFFFAOYSA-N 0.000 description 1
- QMIBIXKZPBEGTE-UHFFFAOYSA-N 2-tridecyloxirane Chemical compound CCCCCCCCCCCCCC1CO1 QMIBIXKZPBEGTE-UHFFFAOYSA-N 0.000 description 1
- ZKAPVLMBPUYKKP-UHFFFAOYSA-N 2-undecyloxirane Chemical compound CCCCCCCCCCCC1CO1 ZKAPVLMBPUYKKP-UHFFFAOYSA-N 0.000 description 1
- FDMFUZHCIRHGRG-UHFFFAOYSA-N 3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)C=C FDMFUZHCIRHGRG-UHFFFAOYSA-N 0.000 description 1
- JSECXTYNFBONSF-UHFFFAOYSA-N 3-chloro-1,1,1,2-tetrafluoropropane Chemical compound ClCC(F)C(F)(F)F JSECXTYNFBONSF-UHFFFAOYSA-N 0.000 description 1
- SXFJDZNJHVPHPH-UHFFFAOYSA-N 3-methylpentane-1,5-diol Chemical compound OCCC(C)CCO SXFJDZNJHVPHPH-UHFFFAOYSA-N 0.000 description 1
- MECNWXGGNCJFQJ-UHFFFAOYSA-N 3-piperidin-1-ylpropane-1,2-diol Chemical compound OCC(O)CN1CCCCC1 MECNWXGGNCJFQJ-UHFFFAOYSA-N 0.000 description 1
- WRQOPPZJPSGEDO-UHFFFAOYSA-N 5-oxabicyclo[4.1.0]heptane Chemical compound C1CCOC2CC21 WRQOPPZJPSGEDO-UHFFFAOYSA-N 0.000 description 1
- QLUXGAQOXHOFIO-UHFFFAOYSA-N 6-ethenyl-7-oxabicyclo[4.1.0]hepta-2,4-diene Chemical compound C1=CC=CC2(C=C)C1O2 QLUXGAQOXHOFIO-UHFFFAOYSA-N 0.000 description 1
- XOIZUVFIXICDDB-UHFFFAOYSA-N 6-methyl-4-(2-methyloxiran-2-yl)-7-oxabicyclo[4.1.0]heptane Chemical compound C1CC2OC2(C)CC1C1(C)CO1 XOIZUVFIXICDDB-UHFFFAOYSA-N 0.000 description 1
- 235000021357 Behenic acid Nutrition 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 1
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 description 1
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 101000823778 Homo sapiens Y-box-binding protein 2 Proteins 0.000 description 1
- 235000021353 Lignoceric acid Nutrition 0.000 description 1
- CQXMAMUUWHYSIY-UHFFFAOYSA-N Lignoceric acid Natural products CCCCCCCCCCCCCCCCCCCCCCCC(=O)OCCC1=CC=C(O)C=C1 CQXMAMUUWHYSIY-UHFFFAOYSA-N 0.000 description 1
- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Natural products CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- BAZMYXGARXYAEQ-UHFFFAOYSA-N alpha-ethyl valeric acid Chemical compound CCCC(CC)C(O)=O BAZMYXGARXYAEQ-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 229940116226 behenic acid Drugs 0.000 description 1
- 125000002511 behenyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- DJUWPHRCMMMSCV-UHFFFAOYSA-N bis(7-oxabicyclo[4.1.0]heptan-4-ylmethyl) hexanedioate Chemical compound C1CC2OC2CC1COC(=O)CCCCC(=O)OCC1CC2OC2CC1 DJUWPHRCMMMSCV-UHFFFAOYSA-N 0.000 description 1
- LMMDJMWIHPEQSJ-UHFFFAOYSA-N bis[(3-methyl-7-oxabicyclo[4.1.0]heptan-4-yl)methyl] hexanedioate Chemical compound C1C2OC2CC(C)C1COC(=O)CCCCC(=O)OCC1CC2OC2CC1C LMMDJMWIHPEQSJ-UHFFFAOYSA-N 0.000 description 1
- BMRWNKZVCUKKSR-UHFFFAOYSA-N butane-1,2-diol Chemical compound CCC(O)CO BMRWNKZVCUKKSR-UHFFFAOYSA-N 0.000 description 1
- OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 description 1
- FEXXLIKDYGCVGJ-UHFFFAOYSA-N butyl 8-(3-octyloxiran-2-yl)octanoate Chemical group CCCCCCCCC1OC1CCCCCCCC(=O)OCCCC FEXXLIKDYGCVGJ-UHFFFAOYSA-N 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 125000003901 ceryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940117916 cinnamic aldehyde Drugs 0.000 description 1
- KJPRLNWUNMBNBZ-UHFFFAOYSA-N cinnamic aldehyde Natural products O=CC=CC1=CC=CC=C1 KJPRLNWUNMBNBZ-UHFFFAOYSA-N 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- KFEVDPWXEVUUMW-UHFFFAOYSA-N docosanoic acid Natural products CCCCCCCCCCCCCCCCCCCCCC(=O)OCCC1=CC=C(O)C=C1 KFEVDPWXEVUUMW-UHFFFAOYSA-N 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- OHNNZOOGWXZCPZ-UHFFFAOYSA-N exo-norbornene oxide Chemical compound C1CC2C3OC3C1C2 OHNNZOOGWXZCPZ-UHFFFAOYSA-N 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- UHCBBWUQDAVSMS-UHFFFAOYSA-N fluoroethane Chemical compound CCF UHCBBWUQDAVSMS-UHFFFAOYSA-N 0.000 description 1
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical group FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000000755 henicosyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002818 heptacosyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- YAQXGBBDJYBXKL-UHFFFAOYSA-N iron(2+);1,10-phenanthroline;dicyanide Chemical compound [Fe+2].N#[C-].N#[C-].C1=CN=C2C3=NC=CC=C3C=CC2=C1.C1=CN=C2C3=NC=CC=C3C=CC2=C1 YAQXGBBDJYBXKL-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 125000002463 lignoceryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000006078 metal deactivator Substances 0.000 description 1
- VNXBKJFUJUWOCW-UHFFFAOYSA-N methylcyclopropane Chemical compound CC1CC1 VNXBKJFUJUWOCW-UHFFFAOYSA-N 0.000 description 1
- 125000002819 montanyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001802 myricyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 125000002465 nonacosyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- XRQKARZTFMEBBY-UHFFFAOYSA-N oxiran-2-ylmethyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1CO1 XRQKARZTFMEBBY-UHFFFAOYSA-N 0.000 description 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 125000002460 pentacosyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- GTLACDSXYULKMZ-UHFFFAOYSA-N pentafluoroethane Chemical compound FC(F)C(F)(F)F GTLACDSXYULKMZ-UHFFFAOYSA-N 0.000 description 1
- UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical compound CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 150000008301 phosphite esters Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920013636 polyphenyl ether polymer Polymers 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical class CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 229940032330 sulfuric acid Drugs 0.000 description 1
- QZZGJDVWLFXDLK-UHFFFAOYSA-N tetracosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCC(O)=O QZZGJDVWLFXDLK-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 125000002469 tricosyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- OFHCXWMZXQBQMH-UHFFFAOYSA-N trifluoro(trifluoromethylsulfanyl)methane Chemical compound FC(F)(F)SC(F)(F)F OFHCXWMZXQBQMH-UHFFFAOYSA-N 0.000 description 1
- VPAYJEUHKVESSD-UHFFFAOYSA-N trifluoroiodomethane Chemical compound FC(F)(F)I VPAYJEUHKVESSD-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
- C10M137/12—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having a phosphorus-to-carbon bond
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M171/00—Lubricating compositions characterised by purely physical criteria, e.g. containing as base-material, thickener or additive, ingredients which are characterised exclusively by their numerically specified physical properties, i.e. containing ingredients which are physically well-defined but for which the chemical nature is either unspecified or only very vaguely indicated
- C10M171/008—Lubricant compositions compatible with refrigerants
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
- C10M105/18—Ethers, e.g. epoxides
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
- C10M105/32—Esters
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
- C10M107/20—Lubricating compositions characterised by the base-material being a macromolecular compound containing oxygen
- C10M107/30—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M107/32—Condensation polymers of aldehydes or ketones; Polyesters; Polyethers
- C10M107/34—Polyoxyalkylenes
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
- C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
- C10M129/16—Ethers
- C10M129/18—Epoxides
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
- C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
- C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
- C10M137/04—Phosphate esters
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
- C10M137/12—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having a phosphorus-to-carbon bond
- C10M137/14—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having a phosphorus-to-carbon bond containing sulfur
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
- C10M169/04—Mixtures of base-materials and additives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
- C10M2207/0406—Ethers; Acetals; Ortho-esters; Ortho-carbonates used as base material
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
- C10M2207/042—Epoxides
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/2805—Esters used as base material
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/283—Esters of polyhydroxy compounds
- C10M2207/2835—Esters of polyhydroxy compounds used as base material
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/30—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids
- C10M2207/301—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids used as base material
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/04—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an alcohol or ester thereof; bound to an aldehyde, ketonic, ether, ketal or acetal radical
- C10M2209/043—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an alcohol or ester thereof; bound to an aldehyde, ketonic, ether, ketal or acetal radical used as base material
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/101—Condensation polymers of aldehydes or ketones and phenols, e.g. Also polyoxyalkylene ether derivatives thereof
- C10M2209/1013—Condensation polymers of aldehydes or ketones and phenols, e.g. Also polyoxyalkylene ether derivatives thereof used as base material
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/10—Macromolecular compoundss obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/103—Polyethers, i.e. containing di- or higher polyoxyalkylene groups
- C10M2209/108—Polyethers, i.e. containing di- or higher polyoxyalkylene groups etherified
- C10M2209/1085—Polyethers, i.e. containing di- or higher polyoxyalkylene groups etherified used as base material
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/041—Triaryl phosphates
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
- C10N2020/09—Characteristics associated with water
- C10N2020/097—Refrigerants
- C10N2020/101—Containing Hydrofluorocarbons
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/30—Refrigerators lubricants or compressors lubricants
Definitions
- the present invention relates to a refrigerating machine oil.
- Refrigerating machines such as refrigerators, car air-conditioners, room air-conditioners, and automatic vending machines have compressors for circulating refrigerants through their refrigerating cycles. These compressors are filled with refrigerating machine oils for lubricating slide members. Refrigerating machine oils are required to have properties such as antiwear property and stability.
- Refrigerating machine oils generally contain lubricating base oils and additives which are selected depending on the aforementioned required properties.
- orthophosphate esters, acid phosphate esters, and the like are used as additives (antiwear agents) for improving antiwear property (for example, see Patent Literatures 1 and 2).
- an object of the present invention is to provide a refrigerating machine oil having excellent antiwear property.
- the present invention provides a refrigerating machine oil including a lubricating base oil and a compound represented by the following formula (A): wherein R a and R b each independently represent a monovalent hydrocarbon group, R c represents a divalent hydrocarbon group, X represents a polar group, and Z a and Z b each independently represent oxygen atom or sulfur atom.
- the refrigerating machine oil preferably includes at least one oxygen-containing oil selected from the group consisting of esters and ethers, as the lubricating base oil.
- the refrigerating machine oil further includes an epoxy compound.
- the refrigerating machine oil preferably includes at least one selected from the group consisting of glycidyl ether-based epoxy compounds, glycidyl ester-based epoxy compounds, oxirane compounds, alkyl oxirane compounds, alicyclic epoxy compounds, epoxidized fatty acid monoesters, and epoxidized plant oils, as the epoxy compound.
- the refrigerating machine oil preferably includes at least one selected from the group consisting of glycidyl ether-based epoxy compounds, glycidyl ester-based epoxy compounds, and alicyclic epoxy compounds, as the epoxy compound.
- the polar group represented by X in the formula (A) preferably has an oxygen atom.
- the present invention can provide a refrigerating machine oil having excellent antiwear property.
- a refrigerating machine oil includes a lubricating base oil and a compound represented by the following formula (A): wherein R a and R b each independently represent a monovalent hydrocarbon group, R c represents a divalent hydrocarbon group, X represents a polar group, and Z a and Z b each independently represent oxygen atom or sulfur atom.
- hydrocarbon oils As the lubricating base oil, hydrocarbon oils, oxygen-containing oils, and the like can be used.
- hydrocarbon oil include mineral oil-based hydrocarbon oils and synthetic hydrocarbon oils.
- Oxygen-containing oil include esters, ethers, carbonates, ketones, silicones, and polysiloxanes.
- Mineral oil-based hydrocarbon oils can be obtained by refining a lubricant fraction which can be obtained from atmospheric distillation and vacuum distillation of paraffinic, naphthenic, or other crude oils according to a method(s) such as solvent deasphalting, solvent refining, hydrorefining, hydrogenolysis, solvent dewaxing, hydrodewaxing, clay treatment, and sulfuric-acid treatment. These refining methods may be used alone or in combination of two or more.
- Examples of synthetic hydrocarbon oil include alkylbenzenes, alkylnaphthalenes, poly- ⁇ -olefins (PAO), polybutenes, ethylene- ⁇ -olefin copolymers, and the like.
- alkylbenzenes the following an alkylbenzene (A) and/or an alkylbenzene (B) can be used.
- alkyl group(s) having 1 to 19 carbon atoms in the alkylbenzene (A) include, for example, a methyl group, an ethyl group, a propyl group (including all isomers; the same applies hereinafter), a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, a dodecyl group, a tridecyl group, a tetradecyl group, a pentadecyl group, a hexadecyl group, a heptadecyl group, an octadecyl group, a nonadecyl group, and an eicosyl group.
- alkyl groups may be linear or branched, and is preferably branched in view of stability, viscosity properties, and the like. Especially in view of availability, the alkyl groups are more preferably branched alkyl groups derived from olefin oligomers such as propylene, butene, and isobutylene.
- the number of alkyl groups in the alkylbenzene (A) is 1 to 4, but in view of stability and availability, it is preferably 1 or 2 (that is, monoalkylbenzene, dialkylbenzene, or mixtures of thereof).
- the alkylbenzene (A) may include only one type of alkylbenzene having a unitary structure, or may include a mixture of alkylbenzenes having different structures as long as they include 1 to 4 alkyl groups having 1 to 19 carbon atoms, and the total number of carbon atoms in the alkyl group(s) is 9 to 19.
- alkyl group(s) having 1 to 40 carbon atoms in the alkylbenzene (B) include, for example, a methyl group, an ethyl group, a propyl group (including all isomers; the same applies hereinafter), a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, a dodecyl group, a tridecyl group, a tetradecyl group, a pentadecyl group, a hexadecyl group, a heptadecyl group, an octadecyl group, a nonadecyl group, an icosyl group, a henicosyl group, a docosyl group, a tricosyl group, a tetra
- alkyl groups may be linear or branched, and is preferably branched in view of stability, viscosity properties, and the like. Especially in view of availability, the alkyl groups are more preferably branched alkyl groups derived from olefin oligomers such as propylene, butene, and isobutylene. In view of a higher flash point, the alkyl groups are more preferably linear or branched alkyl groups derived from linear alkylating agents such as normal paraffin, normal- ⁇ -olefin, or halides thereof, and are even more preferably branched alkyl groups.
- the number of alkyl groups in the alkylbenzene (B) is 1 to 4, but in view of stability and availability, it is preferably 1 or 2 (that is, monoalkylbenzene, dialkylbenzene, or mixtures of thereof).
- the alkylbenzene (B) may include only one type of alkylbenzene having a unitary structure, or may include a mixture of alkylbenzenes having different structures as long as they include 1 to 4 alkyl group(s) having 1 to 40 carbon atoms, and the total number of carbon atoms in the alkyl group(s) is 20 to 40.
- a poly- ⁇ -olefins can be obtained as follows: for example, several molecules of a linear olefin having 6 of 18 having a double bond only at one end are polymerized, and then hydrogenated.
- the poly- ⁇ -olefin may be an isoparaffin having a molecular weight distribution mainly including, for example, a trimer or tetramer of ⁇ -decene having 10 carbon atoms or ⁇ -dodecene having 12 carbon atoms.
- ester examples include aromatic esters, dibasic acid esters, polyol esters, complex esters, carbonate esters, and mixtures thereof.
- the ester is preferably a polyol ester or complex ester.
- Polyol esters are esters of polyhydric alcohols and fatty acids.
- saturated fatty acids are preferably used.
- the number of carbon atoms of the fatty acids is preferably 4 to 20, more preferably 4 to 18, even more preferably 4 to 9, and in particular preferably 5 to 9.
- the polyol esters may be partial esters in which some of the hydroxy groups of a polyhydric alcohol remain unesterified, or may be complete esters in which all hydroxy groups are esterified, or may be mixtures of partial esters and complete esters.
- the polyol esters preferably have a hydroxy value of 10 mg KOH/g or less, more preferably 5 mg KOH/g or less, and even more preferably 3 mg KOH/g or less.
- the ratio of fatty acids having 4 to 20 carbon atoms is preferably 20 to 100% by mol based on the total fatty acids of a poly ester, more preferably 50 to 100% by mol, even more preferably 70 to 100% by mol, and in particular preferably 90 to 100% by mol.
- fatty acids having 4 to 20 carbon atoms include butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, nonadecanoic acid, and icosanoic acid. These fatty acids may be linear or branched.
- the fatty acids are preferably branched at the ⁇ and/or ⁇ positions, and more preferably selected from 2-methylpropanoic acid, 2-methylbutanoic acid, 2-methylpentanoic acid, 2-methylhexanoic acid, 2-ethylpentanoic acid, 2-methylheptanoic acid, 2-ethylhexanoic acid, 3,5,5-trimethylhexanoic acid, and 2-ethylhexadecanoic acid, and even more preferably selected from 2-ethylhexanoic acid and 3,5,5- trimethylhexanoic acid.
- the fatty acids may include fatty acids other than those having 4 to 20 carbon atoms.
- the fatty acids other than those having 4 to 20 carbon atoms may have 21 to 24 carbon atoms.
- the fatty acids having 21 to 24 carbon atoms may be henicosanoic acid, docosanoic acid, tricosanoic acid, tetracosanoic acid, and the like, and may be linear or branched.
- a polyhydric alcohol of the polyol esters a polyhydric alcohol having 2 to 6 hydroxy groups is preferably used.
- the number of carbon atoms in the polyhydric alcohol is preferably 4 to 12, more preferably 5 to 10.
- the polyhydric alcohol is preferably a hindered alcohol such as neopentyl glycol, trimethylolethane, trimethylolpropane, trimethylolbutane, di-(trimethylolpropane), tri-(trimethylolpropane), pentaerythritol, and dipentaerythritol.
- pentaerythritol dipentaerythritol, or an alcohol mixture of pentaerythritol and dipentaerythritol in view of compatibility with a refrigerant and hydrolytic stability.
- Complex esters may be synthesized, for example, by the following method (a) or (b):
- a complex ester obtained by the method (b) may produce a relatively strong acid upon hydrolysis during use as a refrigerating machine oil, and thus tends to show somewhat inferior stability as compared with a complex ester obtained by the method (a). Therefore, complex esters for use herein are preferably those obtained by the method (a) which can provide more stable products.
- the complex ester is preferably synthesized from at least one selected from polyhydric alcohols having 2 to 4 hydroxy groups, at least one selected from polybasic acids having 6 to 12 carbon atoms, and at least one selected from monohydric alcohols having 4 to 18 carbon atoms and monovalent fatty acids having 2 to 12 carbon atoms.
- polyhydric alcohols having 2 to 4 hydroxy groups examples include neopentyl glycol, trimethylolpropane, pentaerythritol, and the like.
- the polyhydric alcohols having 2 to 4 hydroxy groups are preferably selected from neopentyl glycol and trimethylolpropane, and more preferably are neopentyl glycol because suitable viscosity can be secured, and good low-temperature properties can be obtained in combination with a complex ester used as a base oil.
- the polyhydric alcohol of a complex ester further include a dihydric alcohol having 2 to 10 carbon atoms other than neopentyl glycol in addition to the polyhydric alcohol having 2 to 4 hydroxy groups.
- dihydric alcohol having 2 to 10 carbon atoms other than neopentyl glycol include ethylene glycol, propanediols, butanediol, pentanediol, hexandiol, 2-methyl-1,3-propanediol, 3-methyl-1,5-pentanediol, 2,2-diethyl-1,3-pentanediol, and the like.
- the above dihydric alcohol is preferably butanediol in view of excellent properties as a lubricating base oil.
- examples of butanediol include 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, 2,3-butanediol, and the like.
- Butanediol is preferably selected from 1,3-butanediol and 1,4-butanediol in order to obtain good properties.
- the amount of a dihydric alcohol having 2 to 10 carbon atoms other than neopentyl glycol is preferably 1.2 mol or less, more preferably 0.8 mol or less, and even more preferably 0.4 mol or less, based on 1 mol of the polyhydric alcohol having 2 to 4 hydroxy groups,.
- polybasic acids having 6 to 12 carbon atoms examples include adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, phthalic acid, trimellitic acid, and the like.
- the above polybasic acids are preferably selected from adipic acid and sebacic acid, and more preferably is adipic acid.
- the amount of a polybasic acid having 6 to 12 carbon atoms is preferably 0.4 mol to 4 mol, more preferably 0.5 mol to 3 mol, and even more preferably 0.6 mol to 2.5 mol, based on 1 mol of the polyhydric alcohol having 2 to 4 hydroxy groups.
- the monohydric alcohols having 4 to 18 carbon atoms include aliphatic alcohols such as butanol, pentanol, hexanol, heptanol, octanol, nonanol, decanol, dodecanol, and oleyl alcohol. These monohydric alcohols may be linear or branched. Especially in view of balanced properties, the monohydric alcohols having 4 to 18 carbon atoms are preferably monohydric alcohols having 6 to 10 carbon atoms, more preferably monohydric alcohols having 8 to 10 carbon atoms. The above monohydric alcohols are more preferably selected from 2-ethylhexanol and 3,5,5-trimethylhexanol because the resulting synthesized complex ester will have good low-temperature properties.
- Examples of the monovalent fatty acids having 2 to 12 carbon atoms include ethanoic acid, propanoic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, dodecanoic acid, and the like. These monovalent fatty acids may be linear or branched.
- the monovalent fatty acids having 2 to 12 carbon atoms are preferably monovalent fatty acids having 8 to 10 carbon atoms. Among these, 2-ethylhexanoic acid and 3,5,5-trimethylhexanoic acid are more preferred in view of low-temperature properties.
- the ether examples include polyvinyl ether, polyalkylene glycol, polyphenyl ether, perfluoroether, and mixtures thereof, and the like.
- the ether is preferably selected from polyvinyl ethers and polyalkylene glycols, and more preferably a polyvinyl ether.
- the polyvinyl ether has a structural unit represented by the following formula (1): wherein R 1 , R 2 , and R 3 may be the same or different from each other, and each represent a hydrogen atom or a hydrocarbon group, and R 4 represents a divalent hydrocarbon group or a divalent ether-linked oxygen-containing hydrocarbon group, and R 5 represents a hydrocarbon group, and m represents an integer of 0 or higher. When m is 2 or higher, multiple R 4 s may be the same or different from each other.
- the number of carbon atoms of hydrocarbon groups represented by R 1 , R 2 , and R 3 is preferably 1 or more, more preferably 2 or more, and even more preferably 3 or more, and are also preferably 8 or less, more preferably 7 or less, and even more preferably 6 or less. At least one of R 1 , R 2 , and R 3 is preferably a hydrogen atom, and more preferably, all of R 2 , R 2 , and R 3 are hydrogen atoms.
- the number of carbon atoms of a divalent hydrocarbon group and ether-linked oxygen-containing hydrocarbon group represented by R 4 is preferably 1 or more, more preferably 2 or more, and even more preferably 3 or more, and are also preferably 10 or less, more preferably 8 or less, and even more preferably 6 or less.
- the divalent ether-linked oxygen-containing hydrocarbon group represented by R 4 may have oxygen on a side chain which can form an ether linkage.
- R 5 is preferably a hydrocarbon group having 1 to 20 carbon atoms.
- this hydrocarbon group include an alkyl group, a cycloalkyl group, a phenyl group, an aryl group, an arylalkyl group, and the like.
- the above hydrocarbon group is preferably an alkyl group, more preferably an alkyl group having 1 to 5 carbon atoms.
- m is preferably 0 or higher, more preferably 1 or higher, and even more preferably 2 or higher, and is also preferably 20 or lower, more preferably 18 or lower, and even more preferably 16 or lower.
- the average value of m in the entire structure units of the polyvinyl ether is preferably 0 to 10.
- the polyvinyl ether may be a homopolymer including one selected from the structural units represented by the formula (1), or may be a copolymer including two or more selected from the structural units represented by the formula (1), or may be a copolymer including a structural unit represented by the formula (1) and a different structural unit.
- lubricity, insulation properties, hygroscopicity, and the like can be further improved while satisfying compatibility of a refrigerating machine oil with a refrigerant.
- the copolymer may be either a block copolymer or a random copolymer.
- the copolymer preferably has a structural unit (1-1) represented by the above formula (1) in which R 5 is an alkyl group having 1 to 3 carbon atoms and a structural unit (1-2) represented by the above formula (1) in which R 5 is an alkyl group having 3 to 20, preferably 3 to 10, and more preferably 3 to 8 carbon atoms.
- R 5 in the structural unit (1-1) is in particular preferably an ethyl group while R 5 in the structural unit (1-2) is in particular preferably an isobutyl group.
- the molar ratio of the structural unit (1-1) and the structural unit (1-2) is preferably 5:95 to 95:5, more preferably 20:80 to 90:10, and even more preferably 70:30 to 90:10.
- compatibility with a refrigerant tends to be able to be further improved, and hygroscopicity tends to be able to be lowered.
- the polyvinyl ether may consist only of a structural unit represented by the above formula (1), or may be a copolymer further including a structural unit represented by the following formula (2): wherein R 6 to R 9 may be the same or different from each other, and each represent a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms. In the latter case, the copolymer may be either a block copolymer or a random copolymer.
- the polyvinyl ether may be manufactured by polymerizing a vinyl ether-base monomer corresponding to a structural unit represented by the formula (1), or by copolymering a vinyl ether-base monomer corresponding to a structural unit represented by the formula (1) with a hydrocarbon monomer having an olefmic double bond corresponding to a structural unit represented by the formula (2).
- a monomer represented by the following formula (3) is suitable: wherein R 1 , R 2 , R 3 , R 4 , R 5 , and m each have the same definitions as defined for R 1 , R 2 , R 3 , R 4 , R 5 , and m in the formula (1).
- the polyvinyl ether preferably has the following terminal structure (A) or (B).
- polyvinyl ethers those of (a), (b), (c), (d), and (e) listed below are particularly suitable as a base oil.
- the weight average molecular weight of the polyvinyl ether is preferably 500 or more, more preferably 600 or more, and is also preferably 3000 or less, more preferably 2000 or less, and even more preferably 1500 or less.
- the weight average molecular weight of 3000 or less enables a wider range of compositions within which compatibility with a refrigerant can be obtained under low-temperature conditions, preventing poor lubrication in a refrigerant compressor and deteriorated heat exchange in an evaporator.
- the number average molecular weight of the polyvinyl ether is preferably 500 or more, more preferably 600 or more, and is also preferably 3000 or less, more preferably 2000 or less, and even more preferably 1500 or less.
- the polyvinyl ether has a number average molecular weight of 500 or more, superior lubricity in the presence of a refrigerant can be obtained.
- a number average molecular weight of 3000 or less enables a wider range of compositions within which compatibility with a refrigerant can be obtained under low-temperature conditions, preventing poor lubrication in a refrigerant compressor and deteriorated heat exchange in an evaporator.
- the weight average molecular weight and number average molecular weight of the polyvinyl ether both are those determined by the GPC analysis (in terms of polystyrene (standard sample)).
- the weight average molecular weight and number average molecular weight can be measured as follows.
- Dilution is performed using chloroform as a solvent to prepare a solution with a polyvinyl-ether concentration of 1% by mass.
- the solution is analyzed with a GPC instrument (Waters Alliance 2695). Analysis is performed with a refractive index detector at a solvent flow rate of 1 ml/min using a column capable of analyzing a molecular weight of 100 to 10000. It is noted that the relationship between column relation time and molecular weight is separately determined using a polystyrene standard having a known molecular weight to create a calibration curve, and the molecular weight of a sample is then determined from a measured retention time.
- the polyvinyl ether preferably has a degrees of unsaturation of 0.04 meq/g or less, more preferably 0.03 meq/g or less, and even more preferably 0.02 meq/g or less.
- the polyvinyl ether preferably has a peroxide value of a 10.0 meq/kg or less, more preferably 5.0 meq/kg or less, and even more preferably 1.0 meq/kg or less.
- the polyvinyl ether preferably has a carbonyl value of 100 ppm by weight or less, more preferably 50 ppm by weight or less, and even more preferably 20 ppm by weight or less.
- the polyol ester preferably has a hydroxy value of 10 mg KOH/g or less, more preferably 5 mg KOH/g or less, and even more preferably 3 mg KOH/g or less.
- the degree of unsaturation, peroxide value, and carbonyl value in the present invention each refer to a value measured in accordance with the Standard Methods for the Analysis of Fats, Oils and Related Materials defined by the Japan Oil Chemists' Society. That is, with regard to the degree of unsaturation in the present invention, a sample is allowed to react with a Wij's solution (a solution of ICl-acetic acid), and left stand in a dark place, and then excess ICl is reduced into iodine, and that iodine is subsequently titrated with sodium thiosulfate to calculate an iodine value. The iodine value is then converted into a value (meq/g) in terms of vinyl equivalent.
- a Wij's solution a solution of ICl-acetic acid
- This value is used as the degree of unsaturation.
- potassium iodide is added to a sample, and the resulting free iodine is titrated with sodium thiosulfate, and the amount of the free iodine determined is converted into a value (meq/kg) in milliequivalent per kg of the sample. This value is used as the peroxide value.
- carbonyl value in the present invention a sample is allowed to react with 2,4-dinitrophenylhydrazine to generate chromogenic quinonoid ions.
- the absorbance of the sample at 480 nm is measured and converted into a value (ppm by weight) in terms of the amount of carbonyl based on a calibration curve which is pre-determined using cinnamaldehyde as the standard substance. This value is used as the carbonyl value.
- the hydroxy value in the present invention is measured in accordance with JIS K0070:1992.
- polyalkylene glycols examples include polyethylene glycol, polypropylene glycol, polybutylene glycol, and the like. Polyalkylene glycols have oxyethylene, oxypropylene, oxybutylene, and the like as structural units. Polyalkylene glycols having these structural units can be obtained by ring-opening polymerization of ethylene oxide, propylene oxide, or butylene oxide as a raw monomer material.
- Examples of the polyalkylene glycol include compounds represented by the following formula (9): R ⁇ -((OR ⁇ ) f -OR ⁇ ] g (9) wherein in the formula (9), R ⁇ represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an acyl group having 2 to 10 carbon atoms, or a residue of a compound having 2 to 8 hydroxy groups, and R ⁇ represents an alkylene group having 2 to 4 carbon atoms, R ⁇ represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an acyl group having 2 to 10 carbon atoms, and f represents an integer of 1 to 80, and g represents an integer of 1 to 8.
- the alkyl groups represented by R ⁇ and R ⁇ may be any of linear, branched, or cyclic.
- the number of carbon atoms of these alkyl groups is preferably 1 to 10, more preferably 1 to 6.
- compatibility with a refrigerant tends to be decreased.
- the alkyl-group moieties of the acyl groups represented by R ⁇ and R ⁇ may be any of linear, branched, or cyclic.
- the number of carbon atoms of the acyl groups is preferably 2 to 10, more preferably 2 to 6.
- compatibility with a refrigerant may be decreased, resulting in phase separation.
- the groups represented by R ⁇ and R ⁇ are both alkyl groups or both acyl groups
- the groups represented by R ⁇ and R ⁇ may be the same or different.
- g is 2 or higher, the multiple groups represented by R ⁇ and R ⁇ in the same molecule may be the same or different.
- R ⁇ When the group represented by R ⁇ is a residue of a compound having 2 to 8 hydroxy groups, this compound may be chain-like or cyclic.
- R ⁇ and R ⁇ is preferably an alkyl group, more preferably an alkyl group having 1 to 4 carbon atoms, and even more preferably a methyl group.
- both of R ⁇ and R ⁇ are preferably an alkyl group, more preferably an alkyl group having 1 to 4 carbon atoms, and even more preferably a methyl group.
- one of R ⁇ or R ⁇ is an alkyl group (more preferably an alkyl group having 1 to 4 carbon atoms) while the other is a hydrogen atom. More preferably, one is a methyl group while the other is a hydrogen atom.
- both of R ⁇ and R ⁇ are hydrogen atoms.
- R ⁇ represents an alkylene group having 2 to 4 carbon atoms. Specific examples of such an alkylene group include an ethylene group, a propylene group, a butylene group, and the like. Further, oxyalkylene groups as repeating units represented by OR ⁇ include an oxyethylene group, an oxypropylene group, and an oxybutylene group.
- the oxyalkylene groups represented by (OR ⁇ ) f may be composed of one type of oxyalkylene group, or may be composed of two or more types of oxyalkylene group.
- the polyalkylene glycol represented by the formula (9) is preferably a copolymer including an oxyethylene group (EO) and an oxypropylene group (PO) in view of excellent compatibility with a refrigerant and viscosity-temperature properties.
- the ratio (EO/(PO+EO)) of the oxyethylene group to the total of the oxyethylene group and the oxypropylene group is preferably 0.1 to 0.8, more preferably 0.3 to 0.6 in view of excellent seizure load and viscosity-temperature properties.
- EO/(PO+EO) is preferably 0 to 0.5, more preferably 0 to 0.2, even more preferably 0 (that is, a propylene oxide homopolymer).
- f represents the number of repeats (the degree of polymerization) of the oxyalkylene group OR ⁇ , and is an integer of 1 to 80.
- g is an integer of 1 to 8. For example, g is 1 when R ⁇ is an alkyl group or an acyl group. When R ⁇ is a residue of a compound having 2 to 8 hydroxy groups, g corresponds to the number of hydroxy groups in that compound.
- the average value of the product (f ⁇ g) of f and g is preferably 6 to 80 because it will well satisfy required performances as a refrigerating machine oil in a balanced manner.
- the weight average molecular weight of the polyalkylene glycol is preferably 500 or more, more preferably 600 or more, and is also preferably 3000 or less, more preferably 2000 or less, and even more preferably 1500 or less.
- the polyalkylene glycol has a weight average molecular weight of 500 or more, superior lubricity in the presence of a refrigerant can be obtained.
- a weight average molecular weight of 3000 or less enables a wider range of compositions within which compatibility with a refrigerant can be obtained under low-temperature conditions, preventing poor lubrication in a refrigerant compressor and deteriorated heat exchange in an evaporator.
- the number average molecular weight of the polyalkylene glycol is preferably 500 or more, more preferably 600 or more, and is also preferably 3000 or less, more preferably 2000 or less, and even more preferably 1500 or less.
- the polyalkylene glycol has a number average molecular weight of 500 or more, superior lubricity in the presence of a refrigerant can be obtained.
- a number average molecular weight of 3000 or less enables a wider range of compositions within which compatibility with a refrigerant can be obtained under low-temperature conditions, preventing poor lubrication in a refrigerant compressor and deteriorated heat exchange in an evaporator.
- the weight average molecular weight and number average molecular weight of the polyalkylene glycol are both those determined by GPC analysis (in terms of polypropylene glycol (standard sample)).
- the weight average molecular weight and number average molecular weight can be determined as follows.
- Dilution is performed using chloroform as a solvent to prepare a solution with a polyalkylene-glycol concentration of 1% by mass.
- the solution is analyzed with a GPC instrument (Waters Alliance 2695). Analysis is performed with a refractive index detector at a solvent flow rate of 1 ml/min using a column capable of analyzing a molecular weight of 100 to 10000. It is noted that the relationship between column relation time and molecular weight is separately determined using a polyalkylene glycol standard having a known molecular weight to create a calibration curve, and the molecular weight of a sample is then determined from a measured retention time.
- the hydroxy value of the polyalkylene glycol is preferably 100 mg KOH/g or less, more preferably 50 mg KOH/g or less, even more preferably 30 mg KOH/g or less, and most preferably 10 mg KOH/g or less.
- the polyalkylene glycol can be synthesized by a known method ( Mitsuta Shibata et al., "alkylene oxide polymer,” Kaibundo Publishing Co., Ltd.,, November 20th, 1990 ).
- one or more predetermined alkylene oxides are addition-polymerized with an alcohol (R ⁇ OH; R ⁇ has the same definition as defined for R ⁇ in the formula (9)), and terminal hydroxyl groups are further etherified or esterified to obtain the polyalkylene glycol represented by the formula (9).
- the resulting polyalkylene glycol may be either a random copolymer or a block copolymer. However, it is preferably a block copolymer in view of the tendency of having superior oxidation stability and lubricity, and preferably a random copolymer in view of the tendency of having superior low-temperature fluidity.
- the polyalkylene glycol preferably has a degrees of unsaturation of 0.04 meq/g or less, more preferably 0.03 meq/g or less, and even more preferably 0.02 meq/g or less.
- the polyalkylene glycol preferably has a peroxide value of a 10.0 meq/kg or less, more preferably 5.0 meq/kg or less, and even more preferably 1.0 meq/kg or less.
- the polyalkylene glycol preferably has a carbonyl value of 100 ppm by weight or less, more preferably 50 ppm by weight, and even more preferably 20 ppm by weight or less.
- the lubricating base oil is preferably at least one selected from oxygen-containing oils, more preferably at least one selected from esters and ethers.
- the kinematic viscosity at 40°C of the lubricating base oil may be preferably 3 mm 2 /s or more, more preferably 4 mm 2 /s or more, and even more preferably 5 mm 2 /s or more.
- the kinematic viscosity at 40°C of the lubricating base oil may be preferably 1000 mm 2 /s or less, more preferably 500 mm 2 /s or less, and even more preferably 400 mm 2 /s or less.
- the kinematic viscosity at 100°C of the lubricating base oil may be preferably 1 mm 2 /s or more, and more preferably 2 mm 2 /s or more.
- the kinematic viscosity at 100°C of the lubricating base oil may be preferably 100 mm 2 /s or less, and more preferably 50 mm 2 /s or less.
- the kinematic viscosity in the present invention is measured in accordance with JIS K2283:2000.
- the content of the lubricating base oil may be 50% by mass or more, 60% by mass or more, 70% by mass or more, 80% by mass or more, or 90% by mass or more based on the total amount of the refrigerating machine oil.
- the compound represented by the formula (A) is preferably represented by any of the following formulae (A-1) to (A-3): wherein R a , R b , R c , and X have the same meaning as R a , R b , R c , and X in the formula (A), respectively.
- the number of carbon atoms of the monovalent hydrocarbon groups represented by R a and R b may be 2 to 18, 2 to 16, 2 to 14, 2 to 12, 2 to 10, or 2 to 8.
- the monovalent hydrocarbon groups may be linear or branched alkyl groups.
- the number of carbon atoms in the divalent hydrocarbon group represented by R c may be 1 to 4, 1 to 3, 1 to 2, or 1.
- the divalent hydrocarbon group may be a linear or branched alkylene group.
- the polar group represented by X may have an oxygen atom.
- the polar group may be any of -OH group, -COOH group, a -COOR group, -CONHNH 2 group, -CONH 2 group, a -NR 2 group, -CN group, -CH(COOH)CH 2 COOH group, a -CH(COOR)CH 2 COOH group, or any of groups represented by the following Formulae (x-1) to (x-4):
- the polar group represented by X is preferably -OH group, -COOH group, -COOR group, -CH(COOH)CH 2 COOH group, or -CH(COOR)CH 2 COOH group.
- Each R in the above -COOR group, -NR 2 group, and -CH(COOR)CH 2 COOH group may be a monovalent hydrocarbon group, and may be a linear or branched alkyl group.
- the number of carbon atoms of the above monovalent hydrocarbon groups and alkyl groups may be 1 to 12, 1 to 8, or 1 to 2.
- the compound represented by the formula (A) may be a compound represented by the following formula (A-4): wherein R d and R e each represent a linear or branched alkyl group having 2 to 8 carbon atoms, and X a represents -OH group, -COOH group, or -COOR' group (wherein R' represents a linear or branched alkyl group having 1 to 8 carbon atoms).
- the content of the compound represented by the formula (A) may be 0.005% by mass or more, 0.01% by mass or more, or 0.02% by mass or more, and may be 0.1% by mass or less, 0.2% by mass or less, or 1% by mass or less, based on the total amount of the refrigerating machine oil.
- the content of the compound represented by the formula (A) may be 0.005 to 0.1% by mass, 0.005 to 0.2% by mass, 0.005 to 1% by mass, 0.01 to 0.1% by mass, 0.01 to 0.2% by mass, 0.01 to 1% by mass, 0.02 to 0.1% by mass, 0.02 to 0.2% by mass, or 0.02 to 1% by mass, based on the total amount of the refrigerating machine oil.
- the refrigerating machine oil may further include an epoxy compound.
- the epoxy compound include a glycidyl ether-based epoxy compound, a glycidyl ester-based epoxy compound, an oxirane compound, an alkyl oxirane compound, an alicyclic epoxy compound, an epoxidized fatty acid monoester, an epoxidized plant oil, and the like. These epoxy compounds are used alone or in combination of two or more.
- the glycidyl ether-based epoxy compound may be, for example, an aryl glycidyl ether-based epoxy compound or an alkyl glycidyl ether-based epoxy compound, which are represented by the following Formula (B-1): wherein R f represents an aryl group having 6 to 18 carbon atoms or an alkyl group having 5 to 18 carbon atoms.
- the glycidyl ether-based epoxy compound represented by the formula (B-1) is preferably n -butylphenyl glycidyl ether, i -butylphenyl glycidyl ether, sec -butylphenyl glycidyl ether, tert -butylphenyl glycidyl ether, pentylphenyl glycidyl ether, hexylphenyl glycidyl ether, heptylphenyl glycidyl ether, octylphenyl glycidyl ether, nonylphenyl glycidyl ether, decylphenyl glycidyl ether, decyl glycidyl ether, undecyl glycidyl ether, dodecyl glycidyl ether, tridecyl glycidyl ether,
- the glycidyl ether-based epoxy compound may be a compound other than the epoxy compound represented by the formula (B-1), and specifically, may be neopentyl glycol diglycidyl ether, trimethylolpropane triglycidyl ether, pentaerythritol tetraglycidyl ether, 1,6-hexanediol diglycidyl ether, sorbitol polyglycidyl ether, polyalkylene glycol monoglycidyl ether, polyalkylene glycol diglycidyl ether, and the like.
- the glycidyl ester-based epoxy compound may be, for example, a compound represented by the following formula (B-2): wherein R g represents an aryl group having 6 to 18 carbon atoms, an alkyl group having 5 to 18 carbon atoms, or an alkenyl group having 5 to 18 carbon atoms.
- the glycidyl ester-based epoxy compound represented by the formula (B-2) is preferably glycidyl benzoate, glycidyl neodecanoate, glycidyl-2,2-dimethyl octanoate, glycidyl acrylate, or glycidyl methacrylate.
- the alicyclic epoxy compound has a substructure represented by the following formula (B-3): in which the carbon atoms of an epoxy group directly constitutes an alicyclic ring.
- the alicyclic epoxy compound may be, for example, 1,2-epoxycyclohexane, 1,2-epoxycyclopentane, 3',4'-epoxycyclohexylmethyl-3,4-epoxycyclohexane carboxylate, bis(3,4-epoxycyclohexylmethyl)adipate, exo-2,3-epoxynorbornane, bis(3,4-epoxy-6-methylcyclohexylmethyl)adipate, 2-(7-oxabicyclo[4.1.0]hept-3-yl)-spiro(1,3-dioxane-5,3'-[7]oxabicyclo[4 .1.0]heptane, 4-(1'-methylepoxyethyl)-1,2-epoxy-2-methylcyclohexane, or 4-epoxyethyl-1,2-epoxycyclohexane.
- 1,2-epoxycyclohexane 1,2-ep
- allyl oxirane compound examples include 1,2-epoxystyrene, alkyl-1,2-epoxystyrene, and the like.
- alkyl oxirane compound examples include, 1,2-epoxybutane, 1,2-epoxypentane, 1,2-epoxyhexane, 1,2-epoxyheptane, 1,2-epoxyoctane, 1,2-epoxynonane, 1,2-epoxydecane, 1,2-epoxyundecane, 1,2-epoxydodecane, 1,2-epoxytridecane, 1,2-epoxytetradecane, 1,2-epoxypentadecane, 1,2-epoxyhexadecane, 1,2-epoxyheptadecane, 1,2-epoxyoctadecane, 1,2-epoxynonadecane, 1,2-epoxyicosane, and the like.
- Examples of the epoxidized fatty acid monoester include esters of an epoxidized fatty acid having 12 to 20 carbon atoms and an alcohol having 1 to 8 carbon atoms or phenol or alkylphenol.
- the epoxidized fatty acid monoester is preferably butyl epoxystearate, hexyl, benzyl, cyclohexyl, methoxyethyl, octyl, phenyl, or butylphenyl ester.
- Examples of the epoxidized plant oil include epoxy compounds of plant oils such as soybean oil, linseed oil, and cottonseed oil; and the like.
- the refrigerating machine oil includes both the compound represented by the formula (A) and the epoxy compound
- the refrigerating machine oil has not only excellent antiwear property but also excellent stability as compared with a conventional refrigerating machine oil including, for example, an acid phosphate ester and an epoxy compound.
- the epoxy compound is preferably at least one selected from glycidyl ether-based epoxy compounds, glycidyl ester-based epoxy compounds, and alicyclic epoxy compounds, and is more preferably at least one selected from glycidyl ether-based epoxy compounds and glycidyl ester-based epoxy compounds.
- the content of the epoxy compound is preferably 0.1% by mass or more, more preferably 0.15% by mass or more, and even more preferably 0.2% by mass or more, based on the total amount of the refrigerating machine oil.
- the content of an epoxy compound is preferably 5.0% by mass or less, more preferably 3.0% by mass or less, and even more preferably 2.0% by mass or less, based on the total amount of the refrigerating machine oil.
- the refrigerating machine oil may further include other additives.
- the other additives include acid scavengers other than epoxy compounds, antioxidants, extreme pressure agents, oiliness agents, antifoaming agents, metal deactivators, antiwear agents other than the compound represented by the formula (A), viscosity index improvers, pour point depressants, detergent-dispersants, and the like.
- the contents of these additives may be 10% by mass or less or 5% by mass or less based on the total amount of the refrigerating machine oil.
- the refrigerating machine oil preferably further includes at least one of an antioxidant and an antiwear agent other than the compound represented by the formula (A).
- the antioxidant may be a phenol-based antioxidant such as 2,6-di-tert.-butyl- p -cresol and bisphenol A or an amine-based antioxidant such as an alkylphenyl- ⁇ -naphthylamine, and a dialkyldiphenylamine.
- the antiwear agent other than the compound represented by the formula (A) may be a phosphorus-based antiwear agent such as a phosphate ester, an acid phosphate ester, a thiophosphate ester, an amine salt of an acid phosphate ester, a chlorinated phosphate ester, and a phosphite ester.
- a phosphorus-based antiwear agent such as a phosphate ester, an acid phosphate ester, a thiophosphate ester, an amine salt of an acid phosphate ester, a chlorinated phosphate ester, and a phosphite ester.
- the kinematic viscosity at 40°C of the refrigerating machine oil may be preferably 3 mm 2 /s or more, more preferably 4 mm 2 /s or more, and even more preferably 5 mm 2 /s or more.
- the kinematic viscosity at 40°C of the refrigerating machine oil may be preferably 500 mm 2 /s or less, more preferably 400 mm 2 /s or less, and even more preferably 300 mm 2 /s or less.
- the kinematic viscosity at 100°C of the refrigerating machine oil may be preferably 1 mm 2 /s or more, and more preferably 2 mm 2 /s or more.
- the kinematic viscosity at 100°C of the refrigerating machine oil may be 100 mm 2 /s or less, and more preferably 50 mm 2 /s or less.
- the pour point of the refrigerating machine oil may be preferably -10°C or less, and more preferably -20°C or less.
- the pour point in the present invention is measured in accordance with JIS K2269-1987.
- the volume resistivity of the refrigerating machine oil may be preferably 1.0 ⁇ 10 9 ⁇ m or more, more preferably 1.0 ⁇ 10 10 ⁇ m or more, and even more preferably 1.0 ⁇ 10 11 ⁇ m or more.
- the volume resistivity in the present invention is measured at 25°C in accordance with JIS C2101:1999.
- the moisture content of the refrigerating machine oil may be preferably 200 ppm or less based on the total amount of the refrigerating machine oil, more preferably 100 ppm or less, and even more preferably 50 ppm or less.
- the acid value of the refrigerating machine oil may be 1.0 mg KOH/g or less, and more preferably 0.1 mg KOH/g or less.
- the acid value in the present invention is measured in accordance with JIS K2501 :2003.
- the ash content of the refrigerating machine oil may be preferably 100 ppm or less, and more preferably 50 ppm or less.
- the ash content in the present invention is measured in accordance with JIS K2272:1998.
- the refrigerating machine oil according to the present embodiment is used with a refrigerant.
- the refrigerant include saturated hydrofluorocarbon refrigerants, unsaturated hydrofluorocarbon refrigerants, hydrocarbon refrigerants, fluorine-containing ether-based refrigerants such as perfluoro ethers, bis(trifluoromethyl)sulfide refrigerant, trifluoroiodomethane refrigerant, and natural refrigerants such as ammonia and carbon dioxide, and mixed refrigerants including one or two or more of these refrigerants.
- saturated hydrofluorocarbon refrigerant examples include saturated hydrofluorocarbons preferably having 1 to 3 carbon atoms, more preferably having 1 to 2 carbon atoms. Specific examples include difluoromethane (R32), trifluoromethane (R23), pentafluoroethane (R125), 1,1,2,2-tetrafluoroethane (R134), 1,1,1,2-tetrafluoroethane (R134a), 1,1,1-trifluoroethane (R143a), 1,1-difluoroethane (R152a), fluoroethane (R161), 1,1,1,2,3,3,3-heptafluoropropane (R227ea), 1,1,1,2,3,3-hexafluoropropane (R236ea), 1,1,1,3,3,3-hexafluoropropane (R236fa), 1,1,1,3,3-pentafluoropropane (R245fa), 1,1,1,3,3
- An unsaturated hydrofluorocarbon (HFO) refrigerant may be preferably an unsaturated hydrofluorocarbon having 2 to 3 carbon atoms, more preferably a fluoropropene, and even more preferably a fluoropropene having 3 to 5 fluorine atoms.
- An unsaturated hydrofluorocarbon refrigerant is preferably any one or a mixture of two or more of 1,2,3,3,3-pentafluoropropene (HFO-1225ye), 1,3,3,3-tetrafluoropropane (HFO-1234ze), 2,3,3,3-tetrafluoropropane (HFO-1234yf), 1,2,3,3-tetrafluoropropane (HFO-1234ye), and 3,3,3-trifluoropropene (HFO-1243zf).
- An unsaturated hydrofluorocarbon refrigerant is preferably one or two or more selected from HFO-1225ye, HFO-1234ze, and HFO-1234yf, in view of physical properties as a refrigerant.
- An unsaturated hydrofluorocarbon refrigerant may be a fluoroethylene, or more preferably 1,1,2,3-trifluoroethylene (HFO-1123).
- An unsaturated hydrofluorocarbon refrigerant may be 1-chloro-2,3,3,3-tetrafluoropropane (HCFO-1224yd), or may be any of cis-1-chloro-2,3,3,3-tetrafluoropropane (HCFO-1224yd (Z)), trans-1- chloro-2,3,3,3-tetrafluoropropane (HCFO-1224yd (E)), and mixtures thereof.
- the hydrocarbon refrigerant is preferably a hydrocarbon having 1 to 5 carbon atoms, more preferably a hydrocarbon having 2 to 4 carbon atoms.
- examples of the hydrocarbon include methane, ethylene, ethane, propylene, propane (R290), cyclopropane, normal butane, isobutane, cyclobutane, methylcyclopropane, 2-methylbutane, normal pentane, or mixtures of two or more of these.
- a hydrocarbon refrigerant in a gaseous form at 25°C and 1 atmosphere is preferably used, and propane, normal butane, isobutane, 2-methylbutane, or mixtures thereof are more preferably used.
- a refrigerant which can be used along with the refrigerating machine oil according to the present embodiment may be a mixed refrigerant including one or two or more refrigerants selected from the aforementioned refrigerants, and for example, may be a mixed refrigerant of one or two or more refrigerants selected from unsaturated hydrocarbon (HFO) refrigerants and one or two or more refrigerants selected from saturated hydrofluorocarbon (HFC) refrigerants; or may be a mixed refrigerant in which one or two or more refrigerants selected from hydrocarbon refrigerants and natural refrigerants are further mixed with the above mixed refrigerant.
- HFO unsaturated hydrocarbon
- HFC saturated hydrofluorocarbon
- the refrigerant may be, for example, a mixed refrigerant of one or two or more HFO refrigerants selected from HFO-1225ye, HFO-1234ze, HFO-1234yf, HFO-1123, HCFO-1224yd, and the like and one or two or more HFC refrigerants selected from R32, R134a, R125, R152a, R227ea, R236fa, and the like; or may be a mixed refrigerant in which a hydrocarbon refrigerant such as R290 and R600a or a natural refrigerant such as R744 is further mixed with the above mixed refrigerant.
- a mixed refrigerant of one or two or more HFO refrigerants selected from HFO-1225ye, HFO-1234ze, HFO-1234yf, HFO-1123, HCFO-1224yd, and the like and one or two or more HFC refrigerants selected from R32, R134a, R125, R152a, R2
- these mixed refrigerants may be, but not limited to, R444A, R445A, R446A, R447A, R447B, R448A, R449A, R449C, R452B, R454B, R454C, R455A, R456A, R457A, R458A, R459A, R459B, R460B, R461A, R513A, and the like.
- the refrigerating machine oil according to the present embodiment is usually present in a form of a working fluid composition for a refrigerating machine in which it is mixed with a refrigerant. That is, working fluid compositions for a refrigerating machine according to the present embodiment may include the aforementioned refrigerating machine oils and the aforementioned refrigerants.
- the content of the refrigerating machine oil in the working fluid composition for a refrigerating machine may be preferably 1 to 500 parts by mass, and more preferably 2 to 400 parts by mass, based on 100 parts by mass of the refrigerant.
- the refrigerating machine oils and the working fluid compositions for a refrigerating machine according to the present embodiment are suitably used in car air-conditioners with reciprocating, rotary, or hermetic compressors; refrigerators; open or closed car air-conditioners; dehumidifiers; water heaters; freezers; fridge-freezer warehouse; automatic vending machines; showcases; refrigerating machines in chemical plants; refrigerating machines having centrifugal compressors; and the like.
- refrigerating machine oils having the compositions (in "% by mass” based on the total amount of a refrigerating machine oil) shown in Tables 1 to 3 were prepared using the base oils and additives as described below.
- the antiwear property test was performed in accordance with the Four-Ball Extreme Pressure test. The test was performed using SUJ-2 as a rigid ball under the following conditions: test oil: 20 mL, test temperature: 80°C, rotation rate: 1200 rpm, applied load: 294 N, and testing time: 30 minutes. The antiwear property was evaluated based on the average value of wear-track diameters (mm) of fixed balls.
- Example 1 Example 2
- Example 3 Example 4
- Example 5 Example 6
- Example 6 Composition Base oil 1 Remainder Remainder Remainder Remainder Remainder - - Base oil 2 - - - - Remainder - Base oil 3 - - - - - Remainder A1 0.05 - - - 0.05 0.05 A2 - 0.02 0.5 - - - A3 - - - 0.5 - - a1 - - - - - - 1
- Antiwear property Wear-track diameter (mm) 0.57 0.61 0.55 0.62 0.46 0.62
- Refrigerating machine oils of Examples 10 to 16 were also prepared as in Example 8 except that the following base oils were used respectively instead of the base oil 1. These refrigerating machine oils were evaluated for their antiwear property in a similar way as described above, and showed the effect equivalent to those of Examples 1 to 9.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Lubricants (AREA)
Abstract
Description
- The present invention relates to a refrigerating machine oil.
- Refrigerating machines such as refrigerators, car air-conditioners, room air-conditioners, and automatic vending machines have compressors for circulating refrigerants through their refrigerating cycles. These compressors are filled with refrigerating machine oils for lubricating slide members. Refrigerating machine oils are required to have properties such as antiwear property and stability.
- Refrigerating machine oils generally contain lubricating base oils and additives which are selected depending on the aforementioned required properties. Conventionally, orthophosphate esters, acid phosphate esters, and the like are used as additives (antiwear agents) for improving antiwear property (for example, see Patent Literatures 1 and 2).
-
- Patent Literature 1: Japanese Unexamined Patent Publication No.
H11-256182 - Patent Literature 2: Japanese Unexamined Patent Publication No.
2000-282076 - However, there is still a room for improving the antiwear property of refrigerating machine oils containing an orthophosphate ester or an acid phosphate ester as an antiwear agent. It is noted that acid phosphate esters may show higher antiwear property as compared with orthophosphate esters, but may have a problem in terms of stability.
- In view of the above circumstances, the present inventors conducted extensive studies to develop a refrigerating machine oil having improved antiwear property. That is, an object of the present invention is to provide a refrigerating machine oil having excellent antiwear property.
- The present invention provides a refrigerating machine oil including a lubricating base oil and a compound represented by the following formula (A):
- The refrigerating machine oil preferably includes at least one oxygen-containing oil selected from the group consisting of esters and ethers, as the lubricating base oil.
- Preferably, the refrigerating machine oil further includes an epoxy compound.
- The refrigerating machine oil preferably includes at least one selected from the group consisting of glycidyl ether-based epoxy compounds, glycidyl ester-based epoxy compounds, oxirane compounds, alkyl oxirane compounds, alicyclic epoxy compounds, epoxidized fatty acid monoesters, and epoxidized plant oils, as the epoxy compound.
- The refrigerating machine oil preferably includes at least one selected from the group consisting of glycidyl ether-based epoxy compounds, glycidyl ester-based epoxy compounds, and alicyclic epoxy compounds, as the epoxy compound.
- The polar group represented by X in the formula (A) preferably has an oxygen atom.
- The present invention can provide a refrigerating machine oil having excellent antiwear property.
- Below, the embodiments of the present invention will be described in detail.
- A refrigerating machine oil according to one embodiment includes a lubricating base oil and a compound represented by the following formula (A):
- As the lubricating base oil, hydrocarbon oils, oxygen-containing oils, and the like can be used. Examples of the hydrocarbon oil include mineral oil-based hydrocarbon oils and synthetic hydrocarbon oils. Examples of the Oxygen-containing oil include esters, ethers, carbonates, ketones, silicones, and polysiloxanes.
- Mineral oil-based hydrocarbon oils can be obtained by refining a lubricant fraction which can be obtained from atmospheric distillation and vacuum distillation of paraffinic, naphthenic, or other crude oils according to a method(s) such as solvent deasphalting, solvent refining, hydrorefining, hydrogenolysis, solvent dewaxing, hydrodewaxing, clay treatment, and sulfuric-acid treatment. These refining methods may be used alone or in combination of two or more.
- Examples of synthetic hydrocarbon oil include alkylbenzenes, alkylnaphthalenes, poly-α-olefins (PAO), polybutenes, ethylene-α-olefin copolymers, and the like.
- As alkylbenzenes, the following an alkylbenzene (A) and/or an alkylbenzene (B) can be used.
- The alkylbenzene (A): an alkylbenzene having 1 to 4 alkyl groups having 1 to 19 carbon atoms in which the total number of carbon atoms in the alkyl group(s) is 9 to 19 (preferably having 1 to 4 alkyl groups having 1 to 15 carbon atoms in which the total number of carbon atoms in the alkyl group(s) is 9 to 15).
- The alkylbenzene (B): an alkylbenzene having 1 to 4 alkyl groups having 1 to 40 carbon atoms in which the total number of carbon atoms in the alkyl group(s) is 20 to 40 (preferably having 1 to 4 alkyl groups having 1 to 30 carbon atoms in which the total number of carbon atoms in the alkyl group(s) is 20 to 30)
- Specific examples of the alkyl group(s) having 1 to 19 carbon atoms in the alkylbenzene (A) include, for example, a methyl group, an ethyl group, a propyl group (including all isomers; the same applies hereinafter), a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, a dodecyl group, a tridecyl group, a tetradecyl group, a pentadecyl group, a hexadecyl group, a heptadecyl group, an octadecyl group, a nonadecyl group, and an eicosyl group. These alkyl groups may be linear or branched, and is preferably branched in view of stability, viscosity properties, and the like. Especially in view of availability, the alkyl groups are more preferably branched alkyl groups derived from olefin oligomers such as propylene, butene, and isobutylene.
- The number of alkyl groups in the alkylbenzene (A) is 1 to 4, but in view of stability and availability, it is preferably 1 or 2 (that is, monoalkylbenzene, dialkylbenzene, or mixtures of thereof).
- The alkylbenzene (A) may include only one type of alkylbenzene having a unitary structure, or may include a mixture of alkylbenzenes having different structures as long as they include 1 to 4 alkyl groups having 1 to 19 carbon atoms, and the total number of carbon atoms in the alkyl group(s) is 9 to 19.
- Specific examples of the alkyl group(s) having 1 to 40 carbon atoms in the alkylbenzene (B) include, for example, a methyl group, an ethyl group, a propyl group (including all isomers; the same applies hereinafter), a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, a dodecyl group, a tridecyl group, a tetradecyl group, a pentadecyl group, a hexadecyl group, a heptadecyl group, an octadecyl group, a nonadecyl group, an icosyl group, a henicosyl group, a docosyl group, a tricosyl group, a tetracosyl group, a pentacosyl group, a hexacosyl group, a heptacosyl group, an octacosyl group, a nonacosyl group, a triacontyl group, a hentriacontyl group, a dotriacontyl group, a tritriacontyl group, a tetratriacontyl group, a pentatriacontyl group, a hexatriacontyl group, a heptatriacontyl group, an octatriacontyl group, a nonatriacontyl group, and a tetracontyl group. These alkyl groups may be linear or branched, and is preferably branched in view of stability, viscosity properties, and the like. Especially in view of availability, the alkyl groups are more preferably branched alkyl groups derived from olefin oligomers such as propylene, butene, and isobutylene. In view of a higher flash point, the alkyl groups are more preferably linear or branched alkyl groups derived from linear alkylating agents such as normal paraffin, normal-α-olefin, or halides thereof, and are even more preferably branched alkyl groups.
- The number of alkyl groups in the alkylbenzene (B) is 1 to 4, but in view of stability and availability, it is preferably 1 or 2 (that is, monoalkylbenzene, dialkylbenzene, or mixtures of thereof).
- The alkylbenzene (B) may include only one type of alkylbenzene having a unitary structure, or may include a mixture of alkylbenzenes having different structures as long as they include 1 to 4 alkyl group(s) having 1 to 40 carbon atoms, and the total number of carbon atoms in the alkyl group(s) is 20 to 40.
- A poly-α-olefins (PAO) can be obtained as follows: for example, several molecules of a linear olefin having 6 of 18 having a double bond only at one end are polymerized, and then hydrogenated. The poly-α-olefin may be an isoparaffin having a molecular weight distribution mainly including, for example, a trimer or tetramer of α-decene having 10 carbon atoms or α-dodecene having 12 carbon atoms.
- Examples of the ester include aromatic esters, dibasic acid esters, polyol esters, complex esters, carbonate esters, and mixtures thereof. The ester is preferably a polyol ester or complex ester.
- Polyol esters are esters of polyhydric alcohols and fatty acids. As the fatty acids, saturated fatty acids are preferably used. The number of carbon atoms of the fatty acids is preferably 4 to 20, more preferably 4 to 18, even more preferably 4 to 9, and in particular preferably 5 to 9. The polyol esters may be partial esters in which some of the hydroxy groups of a polyhydric alcohol remain unesterified, or may be complete esters in which all hydroxy groups are esterified, or may be mixtures of partial esters and complete esters. The polyol esters preferably have a hydroxy value of 10 mg KOH/g or less, more preferably 5 mg KOH/g or less, and even more preferably 3 mg KOH/g or less.
- The ratio of fatty acids having 4 to 20 carbon atoms is preferably 20 to 100% by mol based on the total fatty acids of a poly ester, more preferably 50 to 100% by mol, even more preferably 70 to 100% by mol, and in particular preferably 90 to 100% by mol.
- Specifically, fatty acids having 4 to 20 carbon atoms include butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, dodecanoic acid, tridecanoic acid, tetradecanoic acid, pentadecanoic acid, hexadecanoic acid, heptadecanoic acid, octadecanoic acid, nonadecanoic acid, and icosanoic acid. These fatty acids may be linear or branched. The fatty acids are preferably branched at the α and/or β positions, and more preferably selected from 2-methylpropanoic acid, 2-methylbutanoic acid, 2-methylpentanoic acid, 2-methylhexanoic acid, 2-ethylpentanoic acid, 2-methylheptanoic acid, 2-ethylhexanoic acid, 3,5,5-trimethylhexanoic acid, and 2-ethylhexadecanoic acid, and even more preferably selected from 2-ethylhexanoic acid and 3,5,5- trimethylhexanoic acid.
- The fatty acids may include fatty acids other than those having 4 to 20 carbon atoms. For example, the fatty acids other than those having 4 to 20 carbon atoms may have 21 to 24 carbon atoms. The fatty acids having 21 to 24 carbon atoms may be henicosanoic acid, docosanoic acid, tricosanoic acid, tetracosanoic acid, and the like, and may be linear or branched.
- As a polyhydric alcohol of the polyol esters, a polyhydric alcohol having 2 to 6 hydroxy groups is preferably used. The number of carbon atoms in the polyhydric alcohol is preferably 4 to 12, more preferably 5 to 10. The polyhydric alcohol is preferably a hindered alcohol such as neopentyl glycol, trimethylolethane, trimethylolpropane, trimethylolbutane, di-(trimethylolpropane), tri-(trimethylolpropane), pentaerythritol, and dipentaerythritol. It is more preferably pentaerythritol, dipentaerythritol, or an alcohol mixture of pentaerythritol and dipentaerythritol in view of compatibility with a refrigerant and hydrolytic stability.
- Complex esters may be synthesized, for example, by the following method (a) or (b):
- (a) a method including: adjusting the molar ratio of a polyhydric alcohol and a polybasic acid, and synthesizing an ester intermediate in which some of the carboxyl groups of the polybasic acid remain unesterified, and then esterifying the remaining carboxyl groups with a monohydric alcohol;
- (b) a method including: adjusting the molar ratio of a polyhydric alcohol and a polybasic acid, and synthesizing an ester intermediate in which some of the hydroxy groups of the polyhydric alcohol remain unesterified, and then esterifying the remaining hydroxy groups with a monovalent fatty acid.
- A complex ester obtained by the method (b) may produce a relatively strong acid upon hydrolysis during use as a refrigerating machine oil, and thus tends to show somewhat inferior stability as compared with a complex ester obtained by the method (a). Therefore, complex esters for use herein are preferably those obtained by the method (a) which can provide more stable products.
- The complex ester is preferably synthesized from at least one selected from polyhydric alcohols having 2 to 4 hydroxy groups, at least one selected from polybasic acids having 6 to 12 carbon atoms, and at least one selected from monohydric alcohols having 4 to 18 carbon atoms and monovalent fatty acids having 2 to 12 carbon atoms.
- Examples of the polyhydric alcohols having 2 to 4 hydroxy groups include neopentyl glycol, trimethylolpropane, pentaerythritol, and the like. The polyhydric alcohols having 2 to 4 hydroxy groups are preferably selected from neopentyl glycol and trimethylolpropane, and more preferably are neopentyl glycol because suitable viscosity can be secured, and good low-temperature properties can be obtained in combination with a complex ester used as a base oil.
- Preferably, the polyhydric alcohol of a complex ester further include a dihydric alcohol having 2 to 10 carbon atoms other than neopentyl glycol in addition to the polyhydric alcohol having 2 to 4 hydroxy groups. Examples of the dihydric alcohol having 2 to 10 carbon atoms other than neopentyl glycol include ethylene glycol, propanediols, butanediol, pentanediol, hexandiol, 2-methyl-1,3-propanediol, 3-methyl-1,5-pentanediol, 2,2-diethyl-1,3-pentanediol, and the like. The above dihydric alcohol is preferably butanediol in view of excellent properties as a lubricating base oil. Examples of butanediol include 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, 2,3-butanediol, and the like. Butanediol is preferably selected from 1,3-butanediol and 1,4-butanediol in order to obtain good properties. The amount of a dihydric alcohol having 2 to 10 carbon atoms other than neopentyl glycol is preferably 1.2 mol or less, more preferably 0.8 mol or less, and even more preferably 0.4 mol or less, based on 1 mol of the polyhydric alcohol having 2 to 4 hydroxy groups,.
- Examples of the polybasic acids having 6 to 12 carbon atoms include adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, phthalic acid, trimellitic acid, and the like. In view of balanced properties of synthesized esters and availability, the above polybasic acids are preferably selected from adipic acid and sebacic acid, and more preferably is adipic acid. The amount of a polybasic acid having 6 to 12 carbon atoms is preferably 0.4 mol to 4 mol, more preferably 0.5 mol to 3 mol, and even more preferably 0.6 mol to 2.5 mol, based on 1 mol of the polyhydric alcohol having 2 to 4 hydroxy groups.
- Examples of the monohydric alcohols having 4 to 18 carbon atoms include aliphatic alcohols such as butanol, pentanol, hexanol, heptanol, octanol, nonanol, decanol, dodecanol, and oleyl alcohol. These monohydric alcohols may be linear or branched. Especially in view of balanced properties, the monohydric alcohols having 4 to 18 carbon atoms are preferably monohydric alcohols having 6 to 10 carbon atoms, more preferably monohydric alcohols having 8 to 10 carbon atoms. The above monohydric alcohols are more preferably selected from 2-ethylhexanol and 3,5,5-trimethylhexanol because the resulting synthesized complex ester will have good low-temperature properties.
- Examples of the monovalent fatty acids having 2 to 12 carbon atoms include ethanoic acid, propanoic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, dodecanoic acid, and the like. These monovalent fatty acids may be linear or branched. The monovalent fatty acids having 2 to 12 carbon atoms are preferably monovalent fatty acids having 8 to 10 carbon atoms. Among these, 2-ethylhexanoic acid and 3,5,5-trimethylhexanoic acid are more preferred in view of low-temperature properties.
- Examples of the ether include polyvinyl ether, polyalkylene glycol, polyphenyl ether, perfluoroether, and mixtures thereof, and the like. The ether is preferably selected from polyvinyl ethers and polyalkylene glycols, and more preferably a polyvinyl ether.
- The polyvinyl ether has a structural unit represented by the following formula (1):
- The number of carbon atoms of hydrocarbon groups represented by R1, R2, and R3 is preferably 1 or more, more preferably 2 or more, and even more preferably 3 or more, and are also preferably 8 or less, more preferably 7 or less, and even more preferably 6 or less. At least one of R1, R2, and R3 is preferably a hydrogen atom, and more preferably, all of R2, R2, and R3 are hydrogen atoms.
- The number of carbon atoms of a divalent hydrocarbon group and ether-linked oxygen-containing hydrocarbon group represented by R4 is preferably 1 or more, more preferably 2 or more, and even more preferably 3 or more, and are also preferably 10 or less, more preferably 8 or less, and even more preferably 6 or less. The divalent ether-linked oxygen-containing hydrocarbon group represented by R4, for example, may have oxygen on a side chain which can form an ether linkage.
- R5 is preferably a hydrocarbon group having 1 to 20 carbon atoms. Examples of this hydrocarbon group include an alkyl group, a cycloalkyl group, a phenyl group, an aryl group, an arylalkyl group, and the like. The above hydrocarbon group is preferably an alkyl group, more preferably an alkyl group having 1 to 5 carbon atoms.
- m is preferably 0 or higher, more preferably 1 or higher, and even more preferably 2 or higher, and is also preferably 20 or lower, more preferably 18 or lower, and even more preferably 16 or lower. The average value of m in the entire structure units of the polyvinyl ether is preferably 0 to 10.
- The polyvinyl ether may be a homopolymer including one selected from the structural units represented by the formula (1), or may be a copolymer including two or more selected from the structural units represented by the formula (1), or may be a copolymer including a structural unit represented by the formula (1) and a different structural unit. When the polyvinyl ether is a copolymer, lubricity, insulation properties, hygroscopicity, and the like can be further improved while satisfying compatibility of a refrigerating machine oil with a refrigerant. Under these circumstances, appropriately selecting the type of a raw monomer, the type of an initiator, the ratio of structural units in a copolymer, and the like can confer the aforementioned various properties on the resulting refrigerating machine oil. The copolymer may be either a block copolymer or a random copolymer.
- When the polyvinyl ether is a copolymer, the copolymer preferably has a structural unit (1-1) represented by the above formula (1) in which R5 is an alkyl group having 1 to 3 carbon atoms and a structural unit (1-2) represented by the above formula (1) in which R5 is an alkyl group having 3 to 20, preferably 3 to 10, and more preferably 3 to 8 carbon atoms. R5 in the structural unit (1-1) is in particular preferably an ethyl group while R5 in the structural unit (1-2) is in particular preferably an isobutyl group. When the polyvinyl ether is a copolymer having the above structural units (1-1) and (1-2), the molar ratio of the structural unit (1-1) and the structural unit (1-2) is preferably 5:95 to 95:5, more preferably 20:80 to 90:10, and even more preferably 70:30 to 90:10. When the above molar ratio falls within the above ranges, compatibility with a refrigerant tends to be able to be further improved, and hygroscopicity tends to be able to be lowered.
- The polyvinyl ether may consist only of a structural unit represented by the above formula (1), or may be a copolymer further including a structural unit represented by the following formula (2):
- The polyvinyl ether may be manufactured by polymerizing a vinyl ether-base monomer corresponding to a structural unit represented by the formula (1), or by copolymering a vinyl ether-base monomer corresponding to a structural unit represented by the formula (1) with a hydrocarbon monomer having an olefmic double bond corresponding to a structural unit represented by the formula (2). As the vinyl ether-based monomer corresponding to a structural unit represented by the formula (1), a monomer represented by the following formula (3) is suitable:
- The polyvinyl ether preferably has the following terminal structure (A) or (B).
- (A) A structure in which one end is represented by the formula (4) or (5) while the other end is represented by the formula (6) or (7).
- (B) A structure in which one end is represented by the above formula (4) or (5) while the other end is represented by the following formula (8):
- Among these polyvinyl ethers, those of (a), (b), (c), (d), and (e) listed below are particularly suitable as a base oil.
- (a) A polyvinyl ether having a structure in which one end is represented by the formula (4) or (5), and the other end is represented by the formula (6) or (7), in which R1, R2, and R3 in the formula (1) are each a hydrogen atom, and m is an integer of 0 to 4, and R4 is a divalent hydrocarbon group having 2 to 4 carbon atoms, and R5 is a hydrocarbon group having 1 to 20 carbon atoms.
- (b) A polyvinyl ether including only a structural unit represented by the formula (1) and having a structure in which one end is represented by the formula (4), and the other end is represented by the formula (6), in which R1, R2, and R3 in the formula (1) are each a hydrogen atom, and m is an integer of 0 to 4, and R4 is a divalent hydrocarbon group having 2 to 4 carbon atoms, and R5 is a hydrocarbon group having 1 to 20 carbon atoms.
- (c) A polyvinyl ether having a structure in which one end is represented by the formula (4) or (5), and the other end is represented by the formula (8), in which R1, R2, and R3 in the formula (1) are each a hydrogen atom, and m is an integer of 0 to 4, and R4 is a divalent hydrocarbon group having 2 to 4 carbon atoms, and R5 is a hydrocarbon group having 1 to 20 carbon atoms.
- (d) A polyvinyl ether including only a structural unit represented by the formula (1) and having a structure in which one end is represented by the formula (5), and the other end is represented by the formula (8), in which R1, R2, and R3 in the formula (1) are each a hydrogen atom, and m is an integer of 0 to 4, and R4 is a divalent hydrocarbon group having 2 to 4 carbon atoms, and R5 is a hydrocarbon group having 1 to 20 carbon atoms.
- (e) A polyvinyl ether of any of the above (a), (b), (c) and (d) having a structural unit in which R5 in the formula (1) is a hydrocarbon group having 1 to 3 carbon atoms and a structural unit in which that R5 is a hydrocarbon group having 3 to 20 carbon atoms.
- The weight average molecular weight of the polyvinyl ether is preferably 500 or more, more preferably 600 or more, and is also preferably 3000 or less, more preferably 2000 or less, and even more preferably 1500 or less. When the polyvinyl ether has a weight average molecular weight of 500 or more, superior lubricity in the presence of a refrigerant can be obtained. A weight average molecular weight of 3000 or less enables a wider range of compositions within which compatibility with a refrigerant can be obtained under low-temperature conditions, preventing poor lubrication in a refrigerant compressor and deteriorated heat exchange in an evaporator.
- The number average molecular weight of the polyvinyl ether is preferably 500 or more, more preferably 600 or more, and is also preferably 3000 or less, more preferably 2000 or less, and even more preferably 1500 or less. When the polyvinyl ether has a number average molecular weight of 500 or more, superior lubricity in the presence of a refrigerant can be obtained. A number average molecular weight of 3000 or less enables a wider range of compositions within which compatibility with a refrigerant can be obtained under low-temperature conditions, preventing poor lubrication in a refrigerant compressor and deteriorated heat exchange in an evaporator.
- The weight average molecular weight and number average molecular weight of the polyvinyl ether both are those determined by the GPC analysis (in terms of polystyrene (standard sample)). For example, the weight average molecular weight and number average molecular weight can be measured as follows.
- Dilution is performed using chloroform as a solvent to prepare a solution with a polyvinyl-ether concentration of 1% by mass. The solution is analyzed with a GPC instrument (Waters Alliance 2695). Analysis is performed with a refractive index detector at a solvent flow rate of 1 ml/min using a column capable of analyzing a molecular weight of 100 to 10000. It is noted that the relationship between column relation time and molecular weight is separately determined using a polystyrene standard having a known molecular weight to create a calibration curve, and the molecular weight of a sample is then determined from a measured retention time.
- The polyvinyl ether preferably has a degrees of unsaturation of 0.04 meq/g or less, more preferably 0.03 meq/g or less, and even more preferably 0.02 meq/g or less. The polyvinyl ether preferably has a peroxide value of a 10.0 meq/kg or less, more preferably 5.0 meq/kg or less, and even more preferably 1.0 meq/kg or less. The polyvinyl ether preferably has a carbonyl value of 100 ppm by weight or less, more preferably 50 ppm by weight or less, and even more preferably 20 ppm by weight or less. The polyol ester preferably has a hydroxy value of 10 mg KOH/g or less, more preferably 5 mg KOH/g or less, and even more preferably 3 mg KOH/g or less.
- The degree of unsaturation, peroxide value, and carbonyl value in the present invention each refer to a value measured in accordance with the Standard Methods for the Analysis of Fats, Oils and Related Materials defined by the Japan Oil Chemists' Society. That is, with regard to the degree of unsaturation in the present invention, a sample is allowed to react with a Wij's solution (a solution of ICl-acetic acid), and left stand in a dark place, and then excess ICl is reduced into iodine, and that iodine is subsequently titrated with sodium thiosulfate to calculate an iodine value. The iodine value is then converted into a value (meq/g) in terms of vinyl equivalent. This value is used as the degree of unsaturation. With regard to the peroxide value in the present invention, potassium iodide is added to a sample, and the resulting free iodine is titrated with sodium thiosulfate, and the amount of the free iodine determined is converted into a value (meq/kg) in milliequivalent per kg of the sample. This value is used as the peroxide value. With regard to the carbonyl value in the present invention, a sample is allowed to react with 2,4-dinitrophenylhydrazine to generate chromogenic quinonoid ions. The absorbance of the sample at 480 nm is measured and converted into a value (ppm by weight) in terms of the amount of carbonyl based on a calibration curve which is pre-determined using cinnamaldehyde as the standard substance. This value is used as the carbonyl value. The hydroxy value in the present invention is measured in accordance with JIS K0070:1992.
- Examples of polyalkylene glycols include polyethylene glycol, polypropylene glycol, polybutylene glycol, and the like. Polyalkylene glycols have oxyethylene, oxypropylene, oxybutylene, and the like as structural units. Polyalkylene glycols having these structural units can be obtained by ring-opening polymerization of ethylene oxide, propylene oxide, or butylene oxide as a raw monomer material.
- Examples of the polyalkylene glycol include compounds represented by the following formula (9):
Rα-((ORβ)f-ORγ]g (9)
wherein in the formula (9), Rα represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an acyl group having 2 to 10 carbon atoms, or a residue of a compound having 2 to 8 hydroxy groups, and Rβ represents an alkylene group having 2 to 4 carbon atoms, Rγ represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an acyl group having 2 to 10 carbon atoms, and f represents an integer of 1 to 80, and g represents an integer of 1 to 8. - The alkyl groups represented by Rα and Rγ may be any of linear, branched, or cyclic. The number of carbon atoms of these alkyl groups is preferably 1 to 10, more preferably 1 to 6. When these alkyl groups have more than 10 carbon atoms, compatibility with a refrigerant tends to be decreased.
- The alkyl-group moieties of the acyl groups represented by Rα and Rγ may be any of linear, branched, or cyclic. The number of carbon atoms of the acyl groups is preferably 2 to 10, more preferably 2 to 6. When the above acyl groups have more than 10 carbon atoms, compatibility with a refrigerant may be decreased, resulting in phase separation.
- When the groups represented by Rα and Rγ are both alkyl groups or both acyl groups, the groups represented by Rα and Rγ may be the same or different. When g is 2 or higher, the multiple groups represented by Rα and Rγ in the same molecule may be the same or different.
- When the group represented by Rα is a residue of a compound having 2 to 8 hydroxy groups, this compound may be chain-like or cyclic.
- In view of excellent compatibility, at least one of Rα and Rγ is preferably an alkyl group, more preferably an alkyl group having 1 to 4 carbon atoms, and even more preferably a methyl group. In view of excellent heat and chemical stability, both of Rα and Rγ are preferably an alkyl group, more preferably an alkyl group having 1 to 4 carbon atoms, and even more preferably a methyl group. In view of manufacturability and cost, preferably, one of Rα or Rγ is an alkyl group (more preferably an alkyl group having 1 to 4 carbon atoms) while the other is a hydrogen atom. More preferably, one is a methyl group while the other is a hydrogen atom. In view of excellent lubricity and sludge solubility, both of Rα and Rγ are hydrogen atoms.
- Rβ represents an alkylene group having 2 to 4 carbon atoms. Specific examples of such an alkylene group include an ethylene group, a propylene group, a butylene group, and the like. Further, oxyalkylene groups as repeating units represented by ORβ include an oxyethylene group, an oxypropylene group, and an oxybutylene group. The oxyalkylene groups represented by (ORβ)f may be composed of one type of oxyalkylene group, or may be composed of two or more types of oxyalkylene group.
- The polyalkylene glycol represented by the formula (9) is preferably a copolymer including an oxyethylene group (EO) and an oxypropylene group (PO) in view of excellent compatibility with a refrigerant and viscosity-temperature properties. In this case, the ratio (EO/(PO+EO)) of the oxyethylene group to the total of the oxyethylene group and the oxypropylene group is preferably 0.1 to 0.8, more preferably 0.3 to 0.6 in view of excellent seizure load and viscosity-temperature properties. In view of excellent hygroscopicity and heat/oxidation stability, EO/(PO+EO) is preferably 0 to 0.5, more preferably 0 to 0.2, even more preferably 0 (that is, a propylene oxide homopolymer).
- f represents the number of repeats (the degree of polymerization) of the oxyalkylene group ORβ, and is an integer of 1 to 80. g is an integer of 1 to 8. For example, g is 1 when Rα is an alkyl group or an acyl group. When Rα is a residue of a compound having 2 to 8 hydroxy groups, g corresponds to the number of hydroxy groups in that compound.
- In the polyalkylene glycol represented by the formula (9), the average value of the product (f × g) of f and g is preferably 6 to 80 because it will well satisfy required performances as a refrigerating machine oil in a balanced manner.
- The weight average molecular weight of the polyalkylene glycol is preferably 500 or more, more preferably 600 or more, and is also preferably 3000 or less, more preferably 2000 or less, and even more preferably 1500 or less. When the polyalkylene glycol has a weight average molecular weight of 500 or more, superior lubricity in the presence of a refrigerant can be obtained. A weight average molecular weight of 3000 or less enables a wider range of compositions within which compatibility with a refrigerant can be obtained under low-temperature conditions, preventing poor lubrication in a refrigerant compressor and deteriorated heat exchange in an evaporator.
- The number average molecular weight of the polyalkylene glycol is preferably 500 or more, more preferably 600 or more, and is also preferably 3000 or less, more preferably 2000 or less, and even more preferably 1500 or less. When the polyalkylene glycol has a number average molecular weight of 500 or more, superior lubricity in the presence of a refrigerant can be obtained. A number average molecular weight of 3000 or less enables a wider range of compositions within which compatibility with a refrigerant can be obtained under low-temperature conditions, preventing poor lubrication in a refrigerant compressor and deteriorated heat exchange in an evaporator.
- The weight average molecular weight and number average molecular weight of the polyalkylene glycol are both those determined by GPC analysis (in terms of polypropylene glycol (standard sample)). For example, the weight average molecular weight and number average molecular weight can be determined as follows.
- Dilution is performed using chloroform as a solvent to prepare a solution with a polyalkylene-glycol concentration of 1% by mass. The solution is analyzed with a GPC instrument (Waters Alliance 2695). Analysis is performed with a refractive index detector at a solvent flow rate of 1 ml/min using a column capable of analyzing a molecular weight of 100 to 10000. It is noted that the relationship between column relation time and molecular weight is separately determined using a polyalkylene glycol standard having a known molecular weight to create a calibration curve, and the molecular weight of a sample is then determined from a measured retention time.
- The hydroxy value of the polyalkylene glycol is preferably 100 mg KOH/g or less, more preferably 50 mg KOH/g or less, even more preferably 30 mg KOH/g or less, and most preferably 10 mg KOH/g or less.
- The polyalkylene glycol can be synthesized by a known method (Mitsuta Shibata et al., "alkylene oxide polymer," Kaibundo Publishing Co., Ltd.,, November 20th, 1990). For example, one or more predetermined alkylene oxides are addition-polymerized with an alcohol (RαOH; Rα has the same definition as defined for Rα in the formula (9)), and terminal hydroxyl groups are further etherified or esterified to obtain the polyalkylene glycol represented by the formula (9). When two or more alkylene oxides are used in the above manufacturing process, the resulting polyalkylene glycol may be either a random copolymer or a block copolymer. However, it is preferably a block copolymer in view of the tendency of having superior oxidation stability and lubricity, and preferably a random copolymer in view of the tendency of having superior low-temperature fluidity.
- The polyalkylene glycol preferably has a degrees of unsaturation of 0.04 meq/g or less, more preferably 0.03 meq/g or less, and even more preferably 0.02 meq/g or less. The polyalkylene glycol preferably has a peroxide value of a 10.0 meq/kg or less, more preferably 5.0 meq/kg or less, and even more preferably 1.0 meq/kg or less. The polyalkylene glycol preferably has a carbonyl value of 100 ppm by weight or less, more preferably 50 ppm by weight, and even more preferably 20 ppm by weight or less.
- The lubricating base oil is preferably at least one selected from oxygen-containing oils, more preferably at least one selected from esters and ethers.
- The kinematic viscosity at 40°C of the lubricating base oil may be preferably 3 mm2/s or more, more preferably 4 mm2/s or more, and even more preferably 5 mm2/s or more. The kinematic viscosity at 40°C of the lubricating base oil may be preferably 1000 mm2/s or less, more preferably 500 mm2/s or less, and even more preferably 400 mm2/s or less. The kinematic viscosity at 100°C of the lubricating base oil may be preferably 1 mm2/s or more, and more preferably 2 mm2/s or more. The kinematic viscosity at 100°C of the lubricating base oil may be preferably 100 mm2/s or less, and more preferably 50 mm2/s or less. The kinematic viscosity in the present invention is measured in accordance with JIS K2283:2000.
- The content of the lubricating base oil may be 50% by mass or more, 60% by mass or more, 70% by mass or more, 80% by mass or more, or 90% by mass or more based on the total amount of the refrigerating machine oil.
-
- The number of carbon atoms of the monovalent hydrocarbon groups represented by Ra and Rb may be 2 to 18, 2 to 16, 2 to 14, 2 to 12, 2 to 10, or 2 to 8. The monovalent hydrocarbon groups may be linear or branched alkyl groups. The number of carbon atoms in the divalent hydrocarbon group represented by Rc may be 1 to 4, 1 to 3, 1 to 2, or 1. The divalent hydrocarbon group may be a linear or branched alkylene group.
- The polar group represented by X may have an oxygen atom. For example, the polar group may be any of -OH group, -COOH group, a -COOR group, -CONHNH2 group, -CONH2 group, a -NR2 group, -CN group, -CH(COOH)CH2COOH group, a -CH(COOR)CH2COOH group, or any of groups represented by the following Formulae (x-1) to (x-4):
- The polar group represented by X is preferably -OH group, -COOH group, -COOR group, -CH(COOH)CH2COOH group, or -CH(COOR)CH2COOH group. Each R in the above -COOR group, -NR2 group, and -CH(COOR)CH2COOH group may be a monovalent hydrocarbon group, and may be a linear or branched alkyl group. The number of carbon atoms of the above monovalent hydrocarbon groups and alkyl groups may be 1 to 12, 1 to 8, or 1 to 2.
- In a preferred aspect, the compound represented by the formula (A) may be a compound represented by the following formula (A-4):
- The content of the compound represented by the formula (A) may be 0.005% by mass or more, 0.01% by mass or more, or 0.02% by mass or more, and may be 0.1% by mass or less, 0.2% by mass or less, or 1% by mass or less, based on the total amount of the refrigerating machine oil. The content of the compound represented by the formula (A) may be 0.005 to 0.1% by mass, 0.005 to 0.2% by mass, 0.005 to 1% by mass, 0.01 to 0.1% by mass, 0.01 to 0.2% by mass, 0.01 to 1% by mass, 0.02 to 0.1% by mass, 0.02 to 0.2% by mass, or 0.02 to 1% by mass, based on the total amount of the refrigerating machine oil.
- The refrigerating machine oil may further include an epoxy compound. Examples of the epoxy compound include a glycidyl ether-based epoxy compound, a glycidyl ester-based epoxy compound, an oxirane compound, an alkyl oxirane compound, an alicyclic epoxy compound, an epoxidized fatty acid monoester, an epoxidized plant oil, and the like. These epoxy compounds are used alone or in combination of two or more.
- The glycidyl ether-based epoxy compound may be, for example, an aryl glycidyl ether-based epoxy compound or an alkyl glycidyl ether-based epoxy compound, which are represented by the following Formula (B-1):
- The glycidyl ether-based epoxy compound represented by the formula (B-1) is preferably n-butylphenyl glycidyl ether, i-butylphenyl glycidyl ether, sec-butylphenyl glycidyl ether, tert-butylphenyl glycidyl ether, pentylphenyl glycidyl ether, hexylphenyl glycidyl ether, heptylphenyl glycidyl ether, octylphenyl glycidyl ether, nonylphenyl glycidyl ether, decylphenyl glycidyl ether, decyl glycidyl ether, undecyl glycidyl ether, dodecyl glycidyl ether, tridecyl glycidyl ether, tetradecyl glycidyl ether, or 2-ethylhexyl glycidyl ether.
- The glycidyl ether-based epoxy compound may be a compound other than the epoxy compound represented by the formula (B-1), and specifically, may be neopentyl glycol diglycidyl ether, trimethylolpropane triglycidyl ether, pentaerythritol tetraglycidyl ether, 1,6-hexanediol diglycidyl ether, sorbitol polyglycidyl ether, polyalkylene glycol monoglycidyl ether, polyalkylene glycol diglycidyl ether, and the like.
-
- The glycidyl ester-based epoxy compound represented by the formula (B-2) is preferably glycidyl benzoate, glycidyl neodecanoate, glycidyl-2,2-dimethyl octanoate, glycidyl acrylate, or glycidyl methacrylate.
-
- The alicyclic epoxy compound may be, for example, 1,2-epoxycyclohexane, 1,2-epoxycyclopentane, 3',4'-epoxycyclohexylmethyl-3,4-epoxycyclohexane carboxylate, bis(3,4-epoxycyclohexylmethyl)adipate, exo-2,3-epoxynorbornane, bis(3,4-epoxy-6-methylcyclohexylmethyl)adipate, 2-(7-oxabicyclo[4.1.0]hept-3-yl)-spiro(1,3-dioxane-5,3'-[7]oxabicyclo[4 .1.0]heptane, 4-(1'-methylepoxyethyl)-1,2-epoxy-2-methylcyclohexane, or 4-epoxyethyl-1,2-epoxycyclohexane.
- Examples of the allyl oxirane compound include 1,2-epoxystyrene, alkyl-1,2-epoxystyrene, and the like.
- Examples of the alkyl oxirane compound include, 1,2-epoxybutane, 1,2-epoxypentane, 1,2-epoxyhexane, 1,2-epoxyheptane, 1,2-epoxyoctane, 1,2-epoxynonane, 1,2-epoxydecane, 1,2-epoxyundecane, 1,2-epoxydodecane, 1,2-epoxytridecane, 1,2-epoxytetradecane, 1,2-epoxypentadecane, 1,2-epoxyhexadecane, 1,2-epoxyheptadecane, 1,2-epoxyoctadecane, 1,2-epoxynonadecane, 1,2-epoxyicosane, and the like.
- Examples of the epoxidized fatty acid monoester include esters of an epoxidized fatty acid having 12 to 20 carbon atoms and an alcohol having 1 to 8 carbon atoms or phenol or alkylphenol. The epoxidized fatty acid monoester is preferably butyl epoxystearate, hexyl, benzyl, cyclohexyl, methoxyethyl, octyl, phenyl, or butylphenyl ester.
- Examples of the epoxidized plant oil include epoxy compounds of plant oils such as soybean oil, linseed oil, and cottonseed oil; and the like.
- When the refrigerating machine oil includes both the compound represented by the formula (A) and the epoxy compound, the refrigerating machine oil has not only excellent antiwear property but also excellent stability as compared with a conventional refrigerating machine oil including, for example, an acid phosphate ester and an epoxy compound. In view of simultaneous achievement of antiwear property and stability, the epoxy compound is preferably at least one selected from glycidyl ether-based epoxy compounds, glycidyl ester-based epoxy compounds, and alicyclic epoxy compounds, and is more preferably at least one selected from glycidyl ether-based epoxy compounds and glycidyl ester-based epoxy compounds.
- In view of improved stability, the content of the epoxy compound is preferably 0.1% by mass or more, more preferably 0.15% by mass or more, and even more preferably 0.2% by mass or more, based on the total amount of the refrigerating machine oil. In view of improved lubricity, the content of an epoxy compound is preferably 5.0% by mass or less, more preferably 3.0% by mass or less, and even more preferably 2.0% by mass or less, based on the total amount of the refrigerating machine oil.
- The refrigerating machine oil may further include other additives. Examples of the other additives include acid scavengers other than epoxy compounds, antioxidants, extreme pressure agents, oiliness agents, antifoaming agents, metal deactivators, antiwear agents other than the compound represented by the formula (A), viscosity index improvers, pour point depressants, detergent-dispersants, and the like. The contents of these additives may be 10% by mass or less or 5% by mass or less based on the total amount of the refrigerating machine oil.
- Among the aforementioned other additives, the refrigerating machine oil preferably further includes at least one of an antioxidant and an antiwear agent other than the compound represented by the formula (A). The antioxidant may be a phenol-based antioxidant such as 2,6-di-tert.-butyl-p-cresol and bisphenol A or an amine-based antioxidant such as an alkylphenyl-α-naphthylamine, and a dialkyldiphenylamine. The antiwear agent other than the compound represented by the formula (A) may be a phosphorus-based antiwear agent such as a phosphate ester, an acid phosphate ester, a thiophosphate ester, an amine salt of an acid phosphate ester, a chlorinated phosphate ester, and a phosphite ester.
- The kinematic viscosity at 40°C of the refrigerating machine oil may be preferably 3 mm2/s or more, more preferably 4 mm2/s or more, and even more preferably 5 mm2/s or more. The kinematic viscosity at 40°C of the refrigerating machine oil may be preferably 500 mm2/s or less, more preferably 400 mm2/s or less, and even more preferably 300 mm2/s or less.
- The kinematic viscosity at 100°C of the refrigerating machine oil may be preferably 1 mm2/s or more, and more preferably 2 mm2/s or more. The kinematic viscosity at 100°C of the refrigerating machine oil may be 100 mm2/s or less, and more preferably 50 mm2/s or less.
- The pour point of the refrigerating machine oil may be preferably -10°C or less, and more preferably -20°C or less. The pour point in the present invention is measured in accordance with JIS K2269-1987.
- The volume resistivity of the refrigerating machine oil may be preferably 1.0×109 Ω·m or more, more preferably 1.0×1010 Ω·m or more, and even more preferably 1.0×1011 Ω·m or more. The volume resistivity in the present invention is measured at 25°C in accordance with JIS C2101:1999.
- The moisture content of the refrigerating machine oil may be preferably 200 ppm or less based on the total amount of the refrigerating machine oil, more preferably 100 ppm or less, and even more preferably 50 ppm or less.
- The acid value of the refrigerating machine oil may be 1.0 mg KOH/g or less, and more preferably 0.1 mg KOH/g or less. The acid value in the present invention is measured in accordance with JIS K2501 :2003.
- The ash content of the refrigerating machine oil may be preferably 100 ppm or less, and more preferably 50 ppm or less. The ash content in the present invention is measured in accordance with JIS K2272:1998.
- The refrigerating machine oil according to the present embodiment is used with a refrigerant. Examples of the refrigerant include saturated hydrofluorocarbon refrigerants, unsaturated hydrofluorocarbon refrigerants, hydrocarbon refrigerants, fluorine-containing ether-based refrigerants such as perfluoro ethers, bis(trifluoromethyl)sulfide refrigerant, trifluoroiodomethane refrigerant, and natural refrigerants such as ammonia and carbon dioxide, and mixed refrigerants including one or two or more of these refrigerants.
- Examples of the saturated hydrofluorocarbon refrigerant include saturated hydrofluorocarbons preferably having 1 to 3 carbon atoms, more preferably having 1 to 2 carbon atoms. Specific examples include difluoromethane (R32), trifluoromethane (R23), pentafluoroethane (R125), 1,1,2,2-tetrafluoroethane (R134), 1,1,1,2-tetrafluoroethane (R134a), 1,1,1-trifluoroethane (R143a), 1,1-difluoroethane (R152a), fluoroethane (R161), 1,1,1,2,3,3,3-heptafluoropropane (R227ea), 1,1,1,2,3,3-hexafluoropropane (R236ea), 1,1,1,3,3,3-hexafluoropropane (R236fa), 1,1,1,3,3-pentafluoropropane (R245fa), 1,1,1,3,3-pentafluorobutane (R365mfc), or mixtures of two or more of these.
- The saturated hydrofluorocarbon refrigerant may be appropriately selected from the followings, depending on uses and required performances, but preferred examples include R32 alone; R23 alone; R134a alone; R125 alone; a mixture of R134a/R32 = 60 to 80% by mass/40 to 20% by mass; a mixture of R32/R125 = 40 to 70% by mass/60 to 30% by mass; a mixture of R125/R143a = 40 to 60% by mass/60 to 40% by mass; a mixture of R134a/R32/R125 = 60% by mass/30% by mass/10% by mass; a mixture of R134a/R32/R125 = 40 to 70% by mass/15 to 35% by mass/5 to 40% by mass; a mixture of R125/R134a/R143a = 35 to 55% by mass /1 to 15% by mass/40 to 60% by mass, and the like. More specifically, the followings may be used: a mixture of R134a/R32 = 70/30% by mass; a mixture of R32/R125 = 60/40% by mass; a mixture of R32/R125 = 50/50% by mass (R410A); a mixture of R32/R124 = 45/55% by mass (R410B); a mixture of R125/R143a = 50/50% by mass (R507C); a mixture of R32/R125/R134a = 30/10/60% by mass; a mixture of R32/R125/R134a = 23/25/52% by mass (R407C); a mixture of R32/R125/R134a = 25/15/60% by mass (R407E); a mixture of R125/R134 a/R143a = 44/4/52% by mass (R404A), and the like.
- An unsaturated hydrofluorocarbon (HFO) refrigerant may be preferably an unsaturated hydrofluorocarbon having 2 to 3 carbon atoms, more preferably a fluoropropene, and even more preferably a fluoropropene having 3 to 5 fluorine atoms. An unsaturated hydrofluorocarbon refrigerant is preferably any one or a mixture of two or more of 1,2,3,3,3-pentafluoropropene (HFO-1225ye), 1,3,3,3-tetrafluoropropane (HFO-1234ze), 2,3,3,3-tetrafluoropropane (HFO-1234yf), 1,2,3,3-tetrafluoropropane (HFO-1234ye), and 3,3,3-trifluoropropene (HFO-1243zf). An unsaturated hydrofluorocarbon refrigerant is preferably one or two or more selected from HFO-1225ye, HFO-1234ze, and HFO-1234yf, in view of physical properties as a refrigerant. An unsaturated hydrofluorocarbon refrigerant may be a fluoroethylene, or more preferably 1,1,2,3-trifluoroethylene (HFO-1123). An unsaturated hydrofluorocarbon refrigerant may be 1-chloro-2,3,3,3-tetrafluoropropane (HCFO-1224yd), or may be any of cis-1-chloro-2,3,3,3-tetrafluoropropane (HCFO-1224yd (Z)), trans-1-chloro-2,3,3,3-tetrafluoropropane (HCFO-1224yd (E)), and mixtures thereof.
- The hydrocarbon refrigerant is preferably a hydrocarbon having 1 to 5 carbon atoms, more preferably a hydrocarbon having 2 to 4 carbon atoms. Specifically, examples of the hydrocarbon include methane, ethylene, ethane, propylene, propane (R290), cyclopropane, normal butane, isobutane, cyclobutane, methylcyclopropane, 2-methylbutane, normal pentane, or mixtures of two or more of these. Among these, a hydrocarbon refrigerant in a gaseous form at 25°C and 1 atmosphere is preferably used, and propane, normal butane, isobutane, 2-methylbutane, or mixtures thereof are more preferably used.
- A refrigerant which can be used along with the refrigerating machine oil according to the present embodiment may be a mixed refrigerant including one or two or more refrigerants selected from the aforementioned refrigerants, and for example, may be a mixed refrigerant of one or two or more refrigerants selected from unsaturated hydrocarbon (HFO) refrigerants and one or two or more refrigerants selected from saturated hydrofluorocarbon (HFC) refrigerants; or may be a mixed refrigerant in which one or two or more refrigerants selected from hydrocarbon refrigerants and natural refrigerants are further mixed with the above mixed refrigerant. More Specifically, the refrigerant may be, for example, a mixed refrigerant of one or two or more HFO refrigerants selected from HFO-1225ye, HFO-1234ze, HFO-1234yf, HFO-1123, HCFO-1224yd, and the like and one or two or more HFC refrigerants selected from R32, R134a, R125, R152a, R227ea, R236fa, and the like; or may be a mixed refrigerant in which a hydrocarbon refrigerant such as R290 and R600a or a natural refrigerant such as R744 is further mixed with the above mixed refrigerant.
- The mixing ratio (mass ratio) of each refrigerant in these mixed refrigerants may be HFO refrigerant/HFC refrigerant/hydrocarbon refrigerant or natural refrigerant = 5 to 95/95 to 5/0 to 20, preferably 15 to 85/85 to 15/0 to 10. More specifically, these mixed refrigerants may be, but not limited to, R444A, R445A, R446A, R447A, R447B, R448A, R449A, R449C, R452B, R454B, R454C, R455A, R456A, R457A, R458A, R459A, R459B, R460B, R461A, R513A, and the like.
- The refrigerating machine oil according to the present embodiment is usually present in a form of a working fluid composition for a refrigerating machine in which it is mixed with a refrigerant. That is, working fluid compositions for a refrigerating machine according to the present embodiment may include the aforementioned refrigerating machine oils and the aforementioned refrigerants. The content of the refrigerating machine oil in the working fluid composition for a refrigerating machine may be preferably 1 to 500 parts by mass, and more preferably 2 to 400 parts by mass, based on 100 parts by mass of the refrigerant.
- The refrigerating machine oils and the working fluid compositions for a refrigerating machine according to the present embodiment are suitably used in car air-conditioners with reciprocating, rotary, or hermetic compressors; refrigerators; open or closed car air-conditioners; dehumidifiers; water heaters; freezers; fridge-freezer warehouse; automatic vending machines; showcases; refrigerating machines in chemical plants; refrigerating machines having centrifugal compressors; and the like.
- Below, the present invention will be described in more detail with reference to Examples, but the present invention shall not be limited to these Examples.
- In Examples and Comparative Examples, refrigerating machine oils having the compositions (in "% by mass" based on the total amount of a refrigerating machine oil) shown in Tables 1 to 3 were prepared using the base oils and additives as described below.
-
- Base oil 1: polyol ester (kinematic viscosity at 40°C: 67.2 mm2/s, viscosity index: 84) of pentaerythritol and a fatty-acid mixture of 2-methylpropanoic acid/3,5,5-trimethylhexanoic acid (mass ratio: 35/65)
- Base oil 2: complex ester (kinematic viscosity at 40°C: 68.2 mm2/s, viscosity index: 144) obtained by reacting neopentyl glycol (1 mol) and 1,4-butanediol (0.3 mol) with adipic acid (2.4 mol) to produce an ester intermediate, further reacting the ester intermediate with 2-ethylhexanol (2.4 mol), and removing residual unreacted materials by distillation
- Base oil 3: polyethyl vinyl ether (number average molecular weight: 1900, kinematic viscosity at 40°C: 71.0 mm2/s, kinematic viscosity at 100°C: 8.6 mm2/s, viscosity index: 89)
- Base oil 4: polyol ester (kinematic viscosity at 40°C: 68 mm2/s) of pentaerythritol and a fatty-acid mixture of 2-ethylhexanoic acid/3,5,5-trimethylhexanoic acid (mass ratio: 50/50)
- Base oil 5: complex ester (kinematic viscosity at 40°C: 150 mm2/s) obtained by reacting neopentyl glycol (1 mol) and 1,4-butanediol (0.3 mol) with adipic acid (2.4 mol) to produce an ester intermediate, further reacting the ester intermediate with 3,5,5-trimethylhexanol (2.4 mol), and removing residual unreacted materials by distillation
- Base oil 6: polyol ester (kinematic viscosity at 40°C: 220 mm2/s) of dipentaerythritol and a fatty-acid mixture of 2-ethylhexanoic acid/3,5,5-trimethylhexanoic acid (mass ratio: 50/50).
- Base oil 7: polyol ester (kinematic viscosity at 40°C: 68 mm2/s) of pentaerythritol and a fatty-acid mixture of pentanoic acid/3,5,5-trimethylhexanoic acid (mass ratio: 25/75)
- Base oil 8: polypropylene glycol dimethyl ether (number average molecular weight (Mn): 1000, kinematic viscosity at 40°C: 46.0 mm2/s, and viscosity index: 190)
-
- A1: compound represented by the following formula (A-1-1):
- A2: compound represented by the following formula (A-1-2):
- A3: compound represented by the following formula (A-1-3):
- a1: tricresyl phosphate
- a2: di(n-octyl) acid phosphate
- B1: glycidyl neodecanoate
- B2: 2-ethylhexyl glycidyl ether
- The antiwear property test was performed as described below for each of the refrigerating machine oils of Examples and Comparative Examples. Results are shown in Tables 1 to 3.
- The antiwear property test was performed in accordance with the Four-Ball Extreme Pressure test. The test was performed using SUJ-2 as a rigid ball under the following conditions: test oil: 20 mL, test temperature: 80°C, rotation rate: 1200 rpm, applied load: 294 N, and testing time: 30 minutes. The antiwear property was evaluated based on the average value of wear-track diameters (mm) of fixed balls.
[Table 1] Example 1 Example 2 Example 3 Example 4 Example 5 Example 6 Composition Base oil 1 Remainder Remainder Remainder Remainder - - Base oil 2 - - - - Remainder - Base oil 3 - - - - - Remainder A1 0.05 - - - 0.05 0.05 A2 - 0.02 0.5 - - - A3 - - - 0.5 - - a1 - - - - - 1 Antiwear property Wear-track diameter (mm) 0.57 0.61 0.55 0.62 0.46 0.62 [Table 2] Comparative Example 1 Comparative Example 2 Comparative Example 3 Comparative Example 4 Composition Base oil 1 Remainder Remainder - - Base oil 2 - - Remainder - Base oil 3 - - Remainder A1 - - - - A2 - - - - A3 - - - - a1 - 1 1 1 Antiwear property wear-track diameter (mm) 0.85 0.8 0.65 0.72 [Table 3] Example 7 Example 8 Example 9 Comparative Example 5 Comparative Example 6 Composition Base oil 1 Remainder Remainder Remainder Remainder Remainder A1 - - - - - A2 0.05 0.05 0.05 - - A3 - - - - - a1 - - - 0.05 0.05 B1 0.5 1 - 0.5 1 B2 - - 1 - - Antiwear property wear-track diameter (mm) 0.56 0.55 0.57 0.87 0.88 - Refrigerating machine oils of Examples 10 to 16 were also prepared as in Example 8 except that the following base oils were used respectively instead of the base oil 1. These refrigerating machine oils were evaluated for their antiwear property in a similar way as described above, and showed the effect equivalent to those of Examples 1 to 9.
- (Example 10) base oil 4
- (Example 11) base oil mixture of Base oil 1: Base oil 4 = 60:40 (mass ratio)
- (Example 12) mixed base oil of Base oil 1: Base oil 5 = 80:20 (mass ratio)
- (Example 13) mixed base oil of Base oil 4: Base oil 5 = 80:20 (mass ratio)
- (Example 14) mixed base oil of Base oil 4: Base oil 6 = 80:20 (mass ratio)
- (Example 15) base oil 7
- (Example 16) base oil 8
- Further, 1% by mass of tricresyl phosphate as an orthophosphate and 0.5% by mass of 2,6-di-tert.-butyl-p-cresol (DBPC) as an antioxidant were added to each of the refrigerating machine oils from Examples 8 and 10 to 16 to prepare refrigerating machine oils of Examples 17 to 24, respectively. These refrigerating machine oils were evaluated for their antiwear property in a similar way as described above, and showed the effect equivalent to those of Examples 1 to 9.
- The stability test was performed as described below for Examples 7 to 9 and Comparative Examples 5 and 6. Results are shown in Table 4.
- Stability in a mixture with a refrigerant was evaluated in accordance with JIS K2211:2009 (autoclave test). That is, 30 g of a refrigerating machine oil adjusted to have a moisture content of 1000 ppm was weighed out into an autoclave along with catalyst (wires of iron, copper, and aluminum, each having an outer diameter of 1.6 mm and a length of 50 mm) and 30 g of R32. Subsequently, the autoclave was sealed and heated at a temperature of 175°C for 168 hours. Refrigerating machine oils after the tests were each measured for their acid values (post-test acid value) in accordance with JIS K2501:2003.
[Table 4] Example 7 Example 8 Example 9 Comparative Example 5 Comparative Example 6 Stability Acid value (mg KOH/g) 0.76 0.16 0.23 1.71 0.40 - Further, stability was evaluated for the refrigerating machine oils of Examples 10 to 24 in a similar way as described above, and showed the effect equivalent to those of Examples 7 to 9. In addition, for Examples 17 to 24, stability was also evaluated as in the above stability test except that HFO-1234yf was used as a refrigerant instead of R32. Results showed that they have good stability.
- Hereinbefore, it should be understood that the present invention shall not be limited to the embodiments and Examples disclosed in the present description, and modifications may appropriately be made without departing from the spirit and scope of the present invention which can be understood from the claims and the entire description. Therefor, it should be understood that refrigerating machine oils with these modifications also fall within the technical scope of the present invention.
Claims (6)
- A refrigerating machine oil comprising:a lubricating base oil; and
- The refrigerating machine oil according to claim 1, comprising at least one oxygen-containing oil selected from the group consisting of esters and ethers, as the lubricating base oil.
- The refrigerating machine oil according to claim 1 or 2, further comprising an epoxy compound.
- The refrigerating machine oil according to claim 3, comprising at least one selected from the group consisting of glycidyl ether-based epoxy compounds, glycidyl ester-based epoxy compounds, oxirane compounds, alkyl oxirane compounds, alicyclic epoxy compounds, epoxidized fatty acid monoesters, and epoxidized plant oils, as the epoxy compound.
- The refrigerating machine oil according to claim 3, comprising at least one selected from the group consisting of glycidyl ether-based epoxy compounds, glycidyl ester-based epoxy compounds, and alicyclic epoxy compounds, as the epoxy compound.
- The refrigerating machine oil according to any one of claims 1 to 5, wherein the polar group has an oxygen atom.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2016148479 | 2016-07-28 | ||
PCT/JP2017/027449 WO2018021533A1 (en) | 2016-07-28 | 2017-07-28 | Refrigerating machine oil |
Publications (3)
Publication Number | Publication Date |
---|---|
EP3492563A1 true EP3492563A1 (en) | 2019-06-05 |
EP3492563A4 EP3492563A4 (en) | 2019-07-31 |
EP3492563B1 EP3492563B1 (en) | 2023-06-14 |
Family
ID=61017439
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP17834535.1A Active EP3492563B1 (en) | 2016-07-28 | 2017-07-28 | Refrigerating machine oil |
Country Status (6)
Country | Link |
---|---|
US (1) | US20190161701A1 (en) |
EP (1) | EP3492563B1 (en) |
JP (1) | JP6964586B2 (en) |
KR (1) | KR102328774B1 (en) |
CN (1) | CN109072114B (en) |
WO (1) | WO2018021533A1 (en) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN108603133B (en) * | 2016-02-24 | 2021-04-16 | Jxtg能源株式会社 | Refrigerating machine oil |
WO2018169039A1 (en) * | 2017-03-17 | 2018-09-20 | Agc株式会社 | Composition for heat cycle system, and heat cycle system |
MX2019015060A (en) * | 2017-06-21 | 2020-08-03 | Honeywell Int Inc | Refrigeration systems and methods. |
CN110437915B (en) * | 2018-05-04 | 2021-12-07 | 上海海立电器有限公司 | Refrigerator oil for hydrofluoroolefin mixture refrigerant and refrigerator system |
WO2020171135A1 (en) * | 2019-02-22 | 2020-08-27 | Jxtgエネルギー株式会社 | Refrigerator oil and refrigerator working fluid composition |
WO2020171133A1 (en) * | 2019-02-22 | 2020-08-27 | Jxtgエネルギー株式会社 | Refrigerator oil and refrigerator working fluid composition |
WO2021106793A1 (en) * | 2019-11-25 | 2021-06-03 | ダイキン工業株式会社 | Refrigerant cycle system |
Family Cites Families (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS536305A (en) * | 1976-07-06 | 1978-01-20 | Sakai Chem Ind Co Ltd | Additives for lubricating oils |
EP0510633A1 (en) * | 1991-04-24 | 1992-10-28 | Japan Sun Oil Company, Ltd. | Lubricating oil composition and use thereof |
JPH05171174A (en) * | 1991-04-30 | 1993-07-09 | Tonen Corp | Lubricant oil composition |
JPH05302093A (en) * | 1992-04-28 | 1993-11-16 | Tonen Corp | Lubricating oil composition |
JPH06145688A (en) * | 1992-11-10 | 1994-05-27 | Nippon San Sekiyu Kk | Lubricating oil composition for refrigerator |
JP3011056B2 (en) * | 1995-06-19 | 2000-02-21 | 住友金属工業株式会社 | Processing method of aluminum and aluminum alloy |
WO1997010319A1 (en) * | 1995-09-13 | 1997-03-20 | Kao Corporation | Lubricating oil composition |
JPH09165593A (en) * | 1995-10-09 | 1997-06-24 | Kao Corp | Lubricating oil composition |
JPH09316479A (en) * | 1996-05-29 | 1997-12-09 | Tonen Corp | Refrigeration oil composition and fluid composition for refrigerator containing the same |
UY24689A1 (en) * | 1996-08-30 | 1997-09-08 | Solutia Inc | NEW WATER-SOLUBLE FLUIDS FOR METAL MACHINING |
JP4009358B2 (en) | 1998-03-10 | 2007-11-14 | 新日本石油株式会社 | Lubricating oil composition for refrigerator using HFC-32 |
JP4316044B2 (en) | 1999-04-01 | 2009-08-19 | 出光興産株式会社 | Refrigerator oil composition |
JP4171575B2 (en) * | 2000-07-24 | 2008-10-22 | 新日本石油株式会社 | Refrigerator oil composition |
JP2008013677A (en) * | 2006-07-06 | 2008-01-24 | Nippon Oil Corp | Refrigerating machine oil |
US8703674B2 (en) * | 2010-03-26 | 2014-04-22 | Adeka Corporation | Lubricating oil composition |
JP5731170B2 (en) * | 2010-11-19 | 2015-06-10 | Jx日鉱日石エネルギー株式会社 | Lubricating oil composition for sliding part provided with aluminum material and lubricating method |
US20140205226A1 (en) * | 2011-07-26 | 2014-07-24 | Nsk Ltd. | Rolling device |
JP6195429B2 (en) * | 2012-03-29 | 2017-09-13 | Jxtgエネルギー株式会社 | Working fluid composition for refrigerator and refrigerator oil |
JP6050213B2 (en) * | 2013-11-01 | 2016-12-21 | Jxエネルギー株式会社 | Lubricating oil composition |
WO2016063833A1 (en) * | 2014-10-23 | 2016-04-28 | Jx日鉱日石エネルギー株式会社 | Refrigeration oil |
-
2017
- 2017-07-28 EP EP17834535.1A patent/EP3492563B1/en active Active
- 2017-07-28 KR KR1020187024670A patent/KR102328774B1/en active IP Right Grant
- 2017-07-28 WO PCT/JP2017/027449 patent/WO2018021533A1/en active Application Filing
- 2017-07-28 US US16/320,803 patent/US20190161701A1/en not_active Abandoned
- 2017-07-28 CN CN201780026257.6A patent/CN109072114B/en active Active
- 2017-07-28 JP JP2018530422A patent/JP6964586B2/en active Active
Also Published As
Publication number | Publication date |
---|---|
WO2018021533A1 (en) | 2018-02-01 |
KR102328774B1 (en) | 2021-11-19 |
EP3492563A4 (en) | 2019-07-31 |
CN109072114B (en) | 2022-03-18 |
JPWO2018021533A1 (en) | 2019-05-23 |
JP6964586B2 (en) | 2021-11-10 |
CN109072114A (en) | 2018-12-21 |
EP3492563B1 (en) | 2023-06-14 |
US20190161701A1 (en) | 2019-05-30 |
KR20190034138A (en) | 2019-04-01 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US11001779B2 (en) | Refrigerator oil and refrigerator working fluid composition | |
EP3492563B1 (en) | Refrigerating machine oil | |
TWI601814B (en) | Refrigeration oil | |
JP6796423B2 (en) | Refrigerating machine oil | |
JP7455109B2 (en) | Refrigerating machine oil and working fluid composition for refrigerators | |
JP7404333B2 (en) | Refrigerating machine oil and working fluid composition for refrigerators | |
JP6796438B2 (en) | Refrigerating machine oil and working fluid composition for refrigerating machine | |
JP6796439B2 (en) | Lubricating oil composition and working fluid composition for refrigerators | |
US11453839B2 (en) | Refrigerator oil | |
JP7470648B2 (en) | Refrigerating machine oil and method for producing same | |
US11993742B2 (en) | Working fluid composition for refrigerator, and refrigerator oil | |
US11485926B2 (en) | Refrigerant oil and method for producing refrigerant oil | |
EP4006128A1 (en) | Refrigerator oil, and working fluid composition for refrigerator |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE INTERNATIONAL PUBLICATION HAS BEEN MADE |
|
PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: REQUEST FOR EXAMINATION WAS MADE |
|
17P | Request for examination filed |
Effective date: 20190220 |
|
AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR |
|
AX | Request for extension of the european patent |
Extension state: BA ME |
|
RIC1 | Information provided on ipc code assigned before grant |
Ipc: C10M 129/18 20060101ALI20190614BHEP Ipc: C10N 40/30 20060101ALI20190614BHEP Ipc: C10M 105/32 20060101ALI20190614BHEP Ipc: C10M 137/04 20060101AFI20190614BHEP Ipc: C10N 30/06 20060101ALI20190614BHEP Ipc: C10M 137/10 20060101ALI20190614BHEP Ipc: C10M 137/02 20060101ALI20190614BHEP Ipc: C10M 107/34 20060101ALI20190614BHEP |
|
A4 | Supplementary search report drawn up and despatched |
Effective date: 20190627 |
|
DAV | Request for validation of the european patent (deleted) | ||
DAX | Request for extension of the european patent (deleted) | ||
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: EXAMINATION IS IN PROGRESS |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: EXAMINATION IS IN PROGRESS |
|
17Q | First examination report despatched |
Effective date: 20210915 |
|
GRAP | Despatch of communication of intention to grant a patent |
Free format text: ORIGINAL CODE: EPIDOSNIGR1 |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: GRANT OF PATENT IS INTENDED |
|
INTG | Intention to grant announced |
Effective date: 20230104 |
|
GRAS | Grant fee paid |
Free format text: ORIGINAL CODE: EPIDOSNIGR3 |
|
GRAA | (expected) grant |
Free format text: ORIGINAL CODE: 0009210 |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE PATENT HAS BEEN GRANTED |
|
AK | Designated contracting states |
Kind code of ref document: B1 Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR |
|
REG | Reference to a national code |
Ref country code: CH Ref legal event code: EP |
|
REG | Reference to a national code |
Ref country code: DE Ref legal event code: R096 Ref document number: 602017070272 Country of ref document: DE |
|
REG | Reference to a national code |
Ref country code: AT Ref legal event code: REF Ref document number: 1579256 Country of ref document: AT Kind code of ref document: T Effective date: 20230715 |
|
REG | Reference to a national code |
Ref country code: LT Ref legal event code: MG9D |
|
REG | Reference to a national code |
Ref country code: NL Ref legal event code: MP Effective date: 20230614 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: SE Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20230614 Ref country code: NO Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20230914 Ref country code: ES Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20230614 |
|
REG | Reference to a national code |
Ref country code: AT Ref legal event code: MK05 Ref document number: 1579256 Country of ref document: AT Kind code of ref document: T Effective date: 20230614 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: RS Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20230614 Ref country code: NL Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20230614 Ref country code: LV Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20230614 Ref country code: LT Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20230614 Ref country code: HR Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20230614 Ref country code: GR Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20230915 |
|
PGFP | Annual fee paid to national office [announced via postgrant information from national office to epo] |
Ref country code: FR Payment date: 20230803 Year of fee payment: 7 Ref country code: DE Payment date: 20230727 Year of fee payment: 7 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: FI Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20230614 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: SK Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20230614 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: IS Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20231014 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: SM Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20230614 Ref country code: SK Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20230614 Ref country code: RO Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20230614 Ref country code: PT Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20231016 Ref country code: IS Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20231014 Ref country code: EE Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20230614 Ref country code: CZ Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20230614 Ref country code: AT Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20230614 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: PL Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20230614 |
|
REG | Reference to a national code |
Ref country code: CH Ref legal event code: PL |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: MC Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20230614 |
|
REG | Reference to a national code |
Ref country code: DE Ref legal event code: R097 Ref document number: 602017070272 Country of ref document: DE |
|
REG | Reference to a national code |
Ref country code: BE Ref legal event code: MM Effective date: 20230731 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: LU Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20230728 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: MC Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20230614 Ref country code: LU Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20230728 |
|
PLBE | No opposition filed within time limit |
Free format text: ORIGINAL CODE: 0009261 |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT |
|
REG | Reference to a national code |
Ref country code: IE Ref legal event code: MM4A |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: DK Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20230614 Ref country code: CH Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20230731 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: SI Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20230614 |
|
26N | No opposition filed |
Effective date: 20240315 |
|
GBPC | Gb: european patent ceased through non-payment of renewal fee |
Effective date: 20230914 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: SI Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20230614 Ref country code: IT Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20230614 Ref country code: BE Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20230731 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: IE Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20230728 |
|
PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: GB Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES Effective date: 20230914 |