JP5256730B2 - Lubricating oil composition for metal working - Google Patents
Lubricating oil composition for metal working Download PDFInfo
- Publication number
- JP5256730B2 JP5256730B2 JP2007337442A JP2007337442A JP5256730B2 JP 5256730 B2 JP5256730 B2 JP 5256730B2 JP 2007337442 A JP2007337442 A JP 2007337442A JP 2007337442 A JP2007337442 A JP 2007337442A JP 5256730 B2 JP5256730 B2 JP 5256730B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- lubricating oil
- epoxy
- oil composition
- epoxy compound
- 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.)
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- 239000010687 lubricating oil Substances 0.000 title claims description 30
- 239000000203 mixture Substances 0.000 title claims description 29
- 238000005555 metalworking Methods 0.000 title claims description 18
- 239000004593 Epoxy Substances 0.000 claims description 48
- 150000001875 compounds Chemical class 0.000 claims description 38
- 239000002199 base oil Substances 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 239000003921 oil Substances 0.000 claims description 17
- 235000019198 oils Nutrition 0.000 claims description 17
- 239000002480 mineral oil Substances 0.000 claims description 13
- 235000010446 mineral oil Nutrition 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 125000001931 aliphatic group Chemical group 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 9
- 239000010775 animal oil Substances 0.000 claims description 6
- 125000003700 epoxy group Chemical group 0.000 claims description 6
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 6
- 239000008158 vegetable oil Substances 0.000 claims description 6
- -1 lard Substances 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 229910052751 metal Inorganic materials 0.000 description 10
- 239000002184 metal Substances 0.000 description 10
- 239000002253 acid Substances 0.000 description 8
- 239000000654 additive Substances 0.000 description 7
- 229920006395 saturated elastomer Polymers 0.000 description 7
- 239000003963 antioxidant agent Substances 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 230000002265 prevention Effects 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- ACIAHEMYLLBZOI-ZZXKWVIFSA-N Unsaturated alcohol Chemical compound CC\C(CO)=C/C ACIAHEMYLLBZOI-ZZXKWVIFSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 125000002723 alicyclic group Chemical group 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000002518 antifoaming agent Substances 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000011056 performance test Methods 0.000 description 3
- 229920001083 polybutene Polymers 0.000 description 3
- 239000001993 wax Substances 0.000 description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical class C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 2
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 2
- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- 235000005956 Cosmos caudatus Nutrition 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 238000005299 abrasion Methods 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000004996 alkyl benzenes Chemical class 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- GVPWHKZIJBODOX-UHFFFAOYSA-N dibenzyl disulfide Chemical compound C=1C=CC=CC=1CSSCC1=CC=CC=C1 GVPWHKZIJBODOX-UHFFFAOYSA-N 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- 235000019197 fats Nutrition 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000003607 modifier Substances 0.000 description 2
- 239000010705 motor oil Substances 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- QQWAKSKPSOFJFF-UHFFFAOYSA-N oxiran-2-ylmethyl 2,2-dimethyloctanoate Chemical compound CCCCCCC(C)(C)C(=O)OCC1CO1 QQWAKSKPSOFJFF-UHFFFAOYSA-N 0.000 description 2
- 239000012188 paraffin wax Substances 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
- 229920013639 polyalphaolefin Polymers 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 239000005077 polysulfide Substances 0.000 description 2
- 229920001021 polysulfide Polymers 0.000 description 2
- 150000008117 polysulfides Polymers 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
- 235000003441 saturated fatty acids Nutrition 0.000 description 2
- 150000004671 saturated fatty acids Chemical class 0.000 description 2
- 231100000241 scar Toxicity 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000003871 sulfonates Chemical class 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
- IKXFIBBKEARMLL-UHFFFAOYSA-N triphenoxy(sulfanylidene)-$l^{5}-phosphane Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=S)OC1=CC=CC=C1 IKXFIBBKEARMLL-UHFFFAOYSA-N 0.000 description 2
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 2
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- PMEKLTYBRXPQIG-UHFFFAOYSA-N (2,3-ditert-butylphenyl) dihydrogen phosphite Chemical compound CC(C)(C)C1=CC=CC(OP(O)O)=C1C(C)(C)C PMEKLTYBRXPQIG-UHFFFAOYSA-N 0.000 description 1
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-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
- QGLWBTPVKHMVHM-KTKRTIGZSA-N (z)-octadec-9-en-1-amine Chemical compound CCCCCCCC\C=C/CCCCCCCCN QGLWBTPVKHMVHM-KTKRTIGZSA-N 0.000 description 1
- OILQNNHOQFRDJH-UHFFFAOYSA-N 1-hexadecylsulfanylhexadecane Chemical compound CCCCCCCCCCCCCCCCSCCCCCCCCCCCCCCCC OILQNNHOQFRDJH-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- ZBADMMCYTSORHN-UHFFFAOYSA-N 2,5-bis(dodecyldisulfanyl)-1,3,4-thiadiazole Chemical compound CCCCCCCCCCCCSSC1=NN=C(SSCCCCCCCCCCCC)S1 ZBADMMCYTSORHN-UHFFFAOYSA-N 0.000 description 1
- VMSIYTPWZLSMOH-UHFFFAOYSA-N 2-(dodecoxymethyl)oxirane Chemical compound CCCCCCCCCCCCOCC1CO1 VMSIYTPWZLSMOH-UHFFFAOYSA-N 0.000 description 1
- NVKSMKFBUGBIGE-UHFFFAOYSA-N 2-(tetradecoxymethyl)oxirane Chemical compound CCCCCCCCCCCCCCOCC1CO1 NVKSMKFBUGBIGE-UHFFFAOYSA-N 0.000 description 1
- PFANXOISJYKQRP-UHFFFAOYSA-N 2-tert-butyl-4-[1-(5-tert-butyl-4-hydroxy-2-methylphenyl)butyl]-5-methylphenol Chemical compound C=1C(C(C)(C)C)=C(O)C=C(C)C=1C(CCC)C1=CC(C(C)(C)C)=C(O)C=C1C PFANXOISJYKQRP-UHFFFAOYSA-N 0.000 description 1
- GPNYZBKIGXGYNU-UHFFFAOYSA-N 2-tert-butyl-6-[(3-tert-butyl-5-ethyl-2-hydroxyphenyl)methyl]-4-ethylphenol Chemical compound CC(C)(C)C1=CC(CC)=CC(CC=2C(=C(C=C(CC)C=2)C(C)(C)C)O)=C1O GPNYZBKIGXGYNU-UHFFFAOYSA-N 0.000 description 1
- BKZXZGWHTRCFPX-UHFFFAOYSA-N 2-tert-butyl-6-methylphenol Chemical compound CC1=CC=CC(C(C)(C)C)=C1O BKZXZGWHTRCFPX-UHFFFAOYSA-N 0.000 description 1
- TWYFTHIEGCZJIE-UHFFFAOYSA-N 3,4-bis(2-ethylhexyl)-7-oxabicyclo[4.1.0]heptane-3,4-dicarboxylic acid Chemical compound C1C(C(O)=O)(CC(CC)CCCC)C(CC(CC)CCCC)(C(O)=O)CC2OC21 TWYFTHIEGCZJIE-UHFFFAOYSA-N 0.000 description 1
- RBVIVTNHCDWKQX-UHFFFAOYSA-N 3,4-dihexyl-7-oxabicyclo[4.1.0]heptane-3,4-dicarboxylic acid Chemical compound C1C(C(O)=O)(CCCCCC)C(CCCCCC)(C(O)=O)CC2OC21 RBVIVTNHCDWKQX-UHFFFAOYSA-N 0.000 description 1
- UNLYOPYLXURRRH-UHFFFAOYSA-N 3,4-dioctyl-7-oxabicyclo[4.1.0]heptane-3,4-dicarboxylic acid Chemical compound C1C(C(O)=O)(CCCCCCCC)C(CCCCCCCC)(C(O)=O)CC2OC21 UNLYOPYLXURRRH-UHFFFAOYSA-N 0.000 description 1
- XYPQVBGRTYHGEY-UHFFFAOYSA-N 3-tert-butyl-4-(2-tert-butyl-4-hydroxy-3-methylphenyl)sulfanyl-2-methylphenol Chemical compound CC1=C(O)C=CC(SC=2C(=C(C)C(O)=CC=2)C(C)(C)C)=C1C(C)(C)C XYPQVBGRTYHGEY-UHFFFAOYSA-N 0.000 description 1
- MDWVSAYEQPLWMX-UHFFFAOYSA-N 4,4'-Methylenebis(2,6-di-tert-butylphenol) Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 MDWVSAYEQPLWMX-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 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 1
- BGYZPELANWFCAI-UHFFFAOYSA-N CCCCCCC1OC1CCCCCCCCC(CC1OC1C1)(C1(CCCCCCCCC1OC1CCCCCC)C(O)=O)C(O)=O Chemical compound CCCCCCC1OC1CCCCCCCCC(CC1OC1C1)(C1(CCCCCCCCC1OC1CCCCCC)C(O)=O)C(O)=O BGYZPELANWFCAI-UHFFFAOYSA-N 0.000 description 1
- WUKGBVSRUHUZKZ-UHFFFAOYSA-N CCCCCCCCC1OC1CCCCCCCCC(CC1OC1C1)(C1(CCCCCCCCC1OC1CCCCCCCC)C(O)=O)C(O)=O Chemical compound CCCCCCCCC1OC1CCCCCCCCC(CC1OC1C1)(C1(CCCCCCCCC1OC1CCCCCCCC)C(O)=O)C(O)=O WUKGBVSRUHUZKZ-UHFFFAOYSA-N 0.000 description 1
- PGDDZIQBCKAVDY-UHFFFAOYSA-N CCCCCCCCCCC(CC1OC1C1)(C1(CCCCCCCCCC)C(O)=O)C(O)=O Chemical compound CCCCCCCCCCC(CC1OC1C1)(C1(CCCCCCCCCC)C(O)=O)C(O)=O PGDDZIQBCKAVDY-UHFFFAOYSA-N 0.000 description 1
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- 239000004215 Carbon black (E152) Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 1
- QAPVYZRWKDXNDK-UHFFFAOYSA-N P,P-Dioctyldiphenylamine Chemical compound C1=CC(CCCCCCCC)=CC=C1NC1=CC=C(CCCCCCCC)C=C1 QAPVYZRWKDXNDK-UHFFFAOYSA-N 0.000 description 1
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
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- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
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- 150000007513 acids Chemical class 0.000 description 1
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- 125000003118 aryl group Chemical group 0.000 description 1
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- IFDVQVHZEKPUSC-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC=CC1C(O)=O IFDVQVHZEKPUSC-UHFFFAOYSA-N 0.000 description 1
- QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical compound OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
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- 239000000539 dimer Substances 0.000 description 1
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
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- 238000011156 evaluation Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
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- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000004668 long chain fatty acids Chemical class 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- KHYKFSXXGRUKRE-UHFFFAOYSA-J molybdenum(4+) tetracarbamodithioate Chemical compound C(N)([S-])=S.[Mo+4].C(N)([S-])=S.C(N)([S-])=S.C(N)([S-])=S KHYKFSXXGRUKRE-UHFFFAOYSA-J 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- ZLNMGXQGGUZIJL-UHFFFAOYSA-N n-octyl-n-phenylnaphthalen-1-amine Chemical compound C=1C=CC2=CC=CC=C2C=1N(CCCCCCCC)C1=CC=CC=C1 ZLNMGXQGGUZIJL-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 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
- 125000001741 organic sulfur group Chemical group 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 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
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920013636 polyphenyl ether polymer Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 150000003902 salicylic acid esters Chemical class 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- JDVPQXZIJDEHAN-UHFFFAOYSA-N succinamic acid Chemical class NC(=O)CCC(O)=O JDVPQXZIJDEHAN-UHFFFAOYSA-N 0.000 description 1
- 150000003443 succinic acid derivatives Chemical class 0.000 description 1
- 150000003900 succinic acid esters Chemical class 0.000 description 1
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical class O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 235000001508 sulfur Nutrition 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 238000010998 test method Methods 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
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Landscapes
- Lubricants (AREA)
Description
本発明は 金属加工用潤滑油に関する。 The present invention relates to a lubricating oil for metal working.
従来、金属加工油用潤滑油には、基油としては鉱油、動植物油、合成油が用いられてきた。しかし、これら基油だけでは金属加工に必要な諸性能を十分満足させる事は出来ず、様々な添加剤を添加することにより性能向上が図られてきた。 Conventionally, mineral oils, animal and vegetable oils, and synthetic oils have been used as base oils for lubricating oils for metalworking oils. However, these base oils alone cannot sufficiently satisfy various performances necessary for metal processing, and performance has been improved by adding various additives.
例えば、金属圧延時の加工性向上、油膜除去性の向上を目的として金属加工油に脂環式エポキシ化合物を含有させる技術が開示されている（特許文献１）。 For example, a technique in which an alicyclic epoxy compound is contained in metal working oil for the purpose of improving workability during metal rolling and improving oil film removal is disclosed (Patent Document 1).
また上記文献の他に、エポキシ化合物を潤滑油に配合する技術としては、脂環式エポキシ化合物を配合することでエンジン油の清浄性が向上する技術が、開示されている（特許文献２）。
さらに、脂環式エポキシ化合物、並びに酸化防止剤併用を含有する潤滑油組成物が、潤滑油の熱安定性及び高温清浄性が向上し２−サイクルエンジン油として好適であることが開示されている（特許文献３）。
しかしながら、これらの特許文献２及び３には、潤滑油組成物に対するエポキシ化合物の添加による摩耗防止性能向上に関しての開示はない。
In addition to the above documents, as a technique for blending an epoxy compound into a lubricating oil, a technique for improving the cleanliness of engine oil by blending an alicyclic epoxy compound is disclosed (Patent Document 2).
Furthermore, it has been disclosed that a lubricating oil composition containing an alicyclic epoxy compound and an antioxidant in combination improves the thermal stability and high temperature cleanability of the lubricating oil and is suitable as a two-cycle engine oil. (Patent Document 3).
However, these Patent Documents 2 and 3 do not disclose the improvement of wear prevention performance by adding an epoxy compound to the lubricating oil composition.
高い摩耗防止性能を有する金属加工用潤滑油組成物を提供する事を目的とする。 It is an object to provide a lubricating oil composition for metal working having high wear prevention performance.
本発明者らは、上記課題を解決すべく鋭意検討の結果、特定の構造を有するエポキシ化合物を、基油に対して配合する事により、金属加工用潤滑油における重要性能である摩耗防止性能が向上することを見いだし、かかる知見に基づいて本発明を完成するに至った。 As a result of intensive studies to solve the above problems, the present inventors have blended an epoxy compound having a specific structure with the base oil, so that the wear prevention performance, which is an important performance in metalworking lubricants, is achieved. Based on this finding, the present invention has been completed.
即ち、本発明は、以下の潤滑油を提供するものである。
（項１）
鉱油、動植物油及び合成油からなる群より選ばれる少なくとも１種の基油及び一般式（１）
Ａ：炭素数１６〜２２のエポキシ基を有する飽和脂肪族炭化水素基
Ｂ：炭素数１６〜２２の飽和脂肪族炭化水素基]
で表される少なくとも１種のエポキシ化合物を含有してなる請求項１に記載の金属加工用潤滑油組成物。
（項２）
一般式（１）で表されるエポキシ化合物の含有量が１〜３０％である項１に記載の金属加工用潤滑油組成物。
（項３）
一般式（１）において、Ｒ１及びＲ２がＡ群より選ばれる置換基である項１又は２に記載の金属加工用潤滑油組成物。
(項４)
一般式（１）
Ａ：炭素数１６〜２２のエポキシ基を有する飽和脂肪族炭化水素基
Ｂ：炭素数１６〜２２の飽和脂肪族炭化水素基]
で表される少なくとも１種のエポキシ化合物を含有せしめることを特徴とする、 金属加工用潤滑油組成物の摩耗防止性能向上方法。
That is, the present invention provides the following lubricating oil.
(Claim 1)
At least one base oil selected from the group consisting of mineral oil, animal and vegetable oils and synthetic oils, and general formula (1)
A: Saturated aliphatic hydrocarbon group having an epoxy group having 16 to 22 carbon atoms B: Saturated aliphatic hydrocarbon group having 16 to 22 carbon atoms]
The lubricating oil composition for metalworking of Claim 1 formed by containing the at least 1 sort (s) of epoxy compound represented by these.
(Section 2)
Item 2. The lubricating oil composition for metalworking according to Item 1, wherein the content of the epoxy compound represented by the general formula (1) is 1 to 30%.
(Section 3)
Item 3. The lubricating oil composition for metalworking according to Item 1 or 2, wherein in General Formula (1), R 1 and R 2 are substituents selected from Group A.
(Section 4)
General formula (1)
A: Saturated aliphatic hydrocarbon group having an epoxy group having 16 to 22 carbon atoms B: Saturated aliphatic hydrocarbon group having 16 to 22 carbon atoms]
A method for improving the wear-preventing performance of a lubricating oil composition for metal working, comprising at least one epoxy compound represented by the formula:
本発明は、特定の構造を有するエポキシ化合物と基油からなる潤滑油組成物は高い耐摩耗性を有することを見出したものである。該潤滑油組成物は、優れた耐摩耗性を有することから金属加工用潤滑油として好適である。 The present invention has been found that a lubricating oil composition comprising an epoxy compound having a specific structure and a base oil has high wear resistance. Since the lubricating oil composition has excellent wear resistance, it is suitable as a lubricating oil for metal working.
[潤滑油組成物]
本発明に係る金属加工用潤滑油組成物は、鉱油、動植物油及び合成油からなる群より選ばれる少なくとも１種の基油及び上記一般式（１）で表されるエポキシ化合物からなる潤滑油組成物である。該潤滑油組成物には必要に応じて後述するその他の添加剤を配合してもよい。
該エポキシ化合物の配合量は、１〜３０重量％が好ましく、５〜２５重量％がより好ましく、１０〜２０重量％が特に好ましい。１重量％未満では充分な摩耗防止効果が得られず、３０重量％を越えて配合したとしても、添加量に見合った性能の向上が得られにくい。
[Lubricating oil composition]
The lubricating oil composition for metal processing according to the present invention comprises a lubricating oil composition comprising at least one base oil selected from the group consisting of mineral oil, animal and vegetable oils and synthetic oils, and an epoxy compound represented by the above general formula (1). It is a thing. You may mix | blend the other additive mentioned later with this lubricating oil composition as needed.
The amount of the epoxy compound is preferably 1 to 30% by weight, more preferably 5 to 25% by weight, and particularly preferably 10 to 20% by weight. If it is less than 1% by weight, a sufficient anti-wear effect cannot be obtained, and even if it exceeds 30% by weight, it is difficult to improve the performance corresponding to the amount added.
また、金属加工用潤滑油組成物の貯蔵安定性の観点から、保管時にエポキシ化合物と基油が均質であること（エポキシ化合物が基油に溶解するか又は基油中にエポキシ化合物が分散するなどして両成分が層分離しないこと）が好ましい。 In addition, from the viewpoint of storage stability of the lubricating oil composition for metal working, the epoxy compound and the base oil are homogeneous during storage (such as the epoxy compound is dissolved in the base oil or the epoxy compound is dispersed in the base oil). Thus, it is preferable that both components are not separated into layers).
[基油]
本発明に係る基油は、鉱油、動植物油及び合成油からなる群より選ばれる少なくとも１種であって、これらの基油は、単独であるいは二種以上組み合わせて使用することができる。
[Base oil]
The base oil according to the present invention is at least one selected from the group consisting of mineral oil, animal and vegetable oils and synthetic oils, and these base oils can be used alone or in combination of two or more.
上記鉱油としては、潤滑油の分野で一般的に基油として用いられる鉱油を使用できる。鉱油としては例えば、原油を常圧蒸留して得られる常圧残油を更に減圧蒸留して得られた潤滑油留分を、溶剤脱れき、溶剤抽出、水素化分解、溶剤脱ろう、水素化精製等の処理を１つ以上行って精製したもの、あるいは鉱油系ワックスやフィッシャートロプシュプロセス等により製造されるワックス（ガス トゥ リキッドワックス）を異性化することによって製造される基油等が例示される。本発明において用いられる鉱油としては、１００℃における動粘度が１．５〜４０ｍｍ２/sの範囲にあるものが好ましい。 As the mineral oil, a mineral oil generally used as a base oil in the field of lubricating oil can be used. As mineral oil, for example, a lubricating oil fraction obtained by further distilling atmospheric residue obtained by atmospheric distillation of crude oil is subjected to solvent removal, solvent extraction, hydrocracking, solvent dewaxing, hydrogenation. Examples include base oils manufactured by isomerizing waxes (gas-to-liquid waxes) that have been refined by performing one or more treatments such as refining, or mineral oil-based waxes or Fischer-Tropsch processes. . The mineral oil used in the present invention preferably has a kinematic viscosity at 100 ° C. in the range of 1.5 to 40 mm 2 / s.
動植物油としては、牛脂、豚脂、パーム油、ヤシ油、ナタネ油、ヒマシ油などが例示される。 Examples of animal and vegetable oils include beef tallow, lard, palm oil, coconut oil, rapeseed oil, castor oil, and the like.
合成油としては、ポリ−α−オレフィン、ポリブテン、アルキルベンゼン、アルキルナフタレンなどの合成炭化水素油及びフィッシャートロプッシュ法によって得られる合成炭化水素の異性化油のほか、有機酸エステル、ポリエーテルなどが挙げられる。 Synthetic oils include synthetic hydrocarbon oils such as poly-α-olefin, polybutene, alkylbenzene, and alkylnaphthalene, and isomerized oils of synthetic hydrocarbons obtained by the Fischer-Tropsch method, as well as organic acid esters and polyethers. It is done.
ポリ−α−オレフィンとしては、炭素数２〜１６のα−オレフィン（例えばエチレン、プロピレン、１−ブテン、１−ヘキセン、１−オクテン、１−デセン、１−ドデセン、１−テトラデセン、１−ヘキサデセンなど）の重合体又は共重合体が例示され、特に１００℃における動粘度が１．５〜４０ｍｍ２/s、粘度指数が１００以上の化合物が好ましく、１００℃における動粘度が３〜３０ｍｍ２/sで、粘度指数が１２０以上のものがより好ましい。 Examples of the poly-α-olefin include α-olefins having 2 to 16 carbon atoms (for example, ethylene, propylene, 1-butene, 1-hexene, 1-octene, 1-decene, 1-dodecene, 1-tetradecene, 1-hexadecene). Etc.), and a compound having a kinematic viscosity at 100 ° C. of 1.5 to 40 mm 2 / s and a viscosity index of 100 or more is preferable, and a kinematic viscosity at 100 ° C. of 3 to 30 mm 2 / It is more preferable that the viscosity index is 120 or more.
ポリブテンとしては、イソブチレンの重合物やイソブチレンとノルマルブチレンとの共重合物が例示され、一般に１００℃の動粘度が２〜６０００ｍｍ２/sの範囲のものが好ましい。 Examples of polybutene include a polymer of isobutylene and a copolymer of isobutylene and normal butylene, and those having a kinematic viscosity at 100 ° C. in the range of 2 to 6000 mm 2 / s are generally preferred.
アルキルベンゼンとしては、炭素数１〜４０の直鎖又は分岐のアルキル基で置換された、分子量が２００〜４５０であるモノアルキルベンゼン、ジアルキルベンゼン、トリアルキルベンゼン、テトラアルキルベンゼンなどが例示される。 Examples of the alkyl benzene include monoalkyl benzene, dialkyl benzene, trialkyl benzene, and tetraalkyl benzene having a molecular weight of 200 to 450, which are substituted with a linear or branched alkyl group having 1 to 40 carbon atoms.
アルキルナフタレンとしては、炭素数１〜３０の直鎖又は分岐のアルキル基で置換されたモノアルキルナフタレン、ジアルキルナフタレンなどが例示される。 Examples of the alkylnaphthalene include monoalkylnaphthalene and dialkylnaphthalene substituted with a linear or branched alkyl group having 1 to 30 carbon atoms.
有機酸エステルとしては、パルミチン酸、ステアリン酸、オレイン酸などの炭素数１０〜２２の直鎖状若しくは分岐鎖状の飽和又は不飽和の脂肪酸と炭素数３〜２２の直鎖状若しくは分岐鎖状の飽和又は不飽和の脂肪族アルコールとのモノエステル類；アジピン酸、アゼライン酸、セバシン酸、ドデカン−２酸などの炭素数６〜１２の脂肪族ジカルボン酸と炭素数３〜２２の直鎖状若しくは分岐鎖状の飽和又は不飽和の脂肪族アルコールとのジエステル類；フタル酸、イソフタル酸、テレフタル酸、トリメリット酸、ピロメリット酸などの芳香族多価カルボン酸若しくはそれらの酸無水物と炭素数３〜２２の直鎖状若しくは分岐鎖状の飽和又は不飽和の脂肪族アルコールとのフルエステル；シクロヘキサンジカルボン酸若しくはその酸無水物と炭素数３〜２２の直鎖状若しくは分岐鎖状の飽和又は不飽和の脂肪族アルコールとのジエステル；ダイマー酸と炭素数３〜２２の直鎖状若しくは分岐鎖状の飽和又は不飽和の脂肪族アルコールとのエステルなどの脂環式多価カルボン酸エステル；及びネオペンチルグリコール、トリメチロールプロパン、ペンタエリスリトールなどのポリオールと炭素数３〜２２の直鎖状若しくは分岐鎖状の飽和又は不飽和の脂肪酸とのフルエステル若しくは部分エステルなどが例示される。 Examples of the organic acid ester include linear or branched saturated or unsaturated fatty acids having 10 to 22 carbon atoms such as palmitic acid, stearic acid, and oleic acid, and linear or branched chains having 3 to 22 carbon atoms. Monoesters with saturated or unsaturated aliphatic alcohols; linear C6-C22 aliphatic dicarboxylic acids such as adipic acid, azelaic acid, sebacic acid, dodecane-2 acid, etc. Or diesters with branched chain saturated or unsaturated aliphatic alcohols; aromatic polycarboxylic acids such as phthalic acid, isophthalic acid, terephthalic acid, trimellitic acid, pyromellitic acid, or their acid anhydrides and carbon A full ester with a linear or branched saturated or unsaturated aliphatic alcohol having 3 to 22; cyclohexanedicarboxylic acid or acid anhydride thereof Diester of C3-C22 linear or branched saturated or unsaturated aliphatic alcohol; Dimer acid and C3-C22 linear or branched saturated or unsaturated aliphatic Alicyclic polycarboxylic acid esters such as esters with alcohols; and polyols such as neopentyl glycol, trimethylolpropane, pentaerythritol, and linear or branched, saturated or unsaturated fatty acids having 3 to 22 carbon atoms And full esters or partial esters.
ポリエーテルとしては、ポリエチレングリコール、ポリプロピレングリコール、オキシエチレン−オキシプロピレン共重合体、ポリエステルエーテル、ポリフェニルエーテルなどが例示され、一般に１００℃の動粘度が２〜４０００ｍｍ２/sの範囲のものが挙げられる。 Examples of the polyether include polyethylene glycol, polypropylene glycol, oxyethylene-oxypropylene copolymer, polyester ether, polyphenyl ether, and the like, generally having a kinematic viscosity at 100 ° C. in the range of 2 to 4000 mm 2 / s. It is done.
上記基油の中でも入手の容易さと潤滑油としての機能等の観点から、基油として鉱油を使用することが好ましい。 Among the above base oils, it is preferable to use a mineral oil as the base oil from the viewpoint of easy availability and function as a lubricating oil.
[エポキシ化合物]
本発明に係るエポキシ化合物は、下記一般式（１）
Ａ：炭素数１６〜２２のエポキシ基を有する飽和脂肪族炭化水素基
Ｂ：炭素数１６〜２２の飽和脂肪族炭化水素基]
で表される化合物である。
上記Ａ群の飽和脂肪族炭化水素基中のエポキシ基の個数としては１個以上であって１〜３個が好ましい。
[Epoxy compound]
The epoxy compound according to the present invention has the following general formula (1)
A: Saturated aliphatic hydrocarbon group having an epoxy group having 16 to 22 carbon atoms B: Saturated aliphatic hydrocarbon group having 16 to 22 carbon atoms]
It is a compound represented by these.
The number of epoxy groups in the saturated aliphatic hydrocarbon group of Group A is 1 or more, preferably 1 to 3.
上記エポキシ化合物は、無水テトラヒドロフタル酸とアルコール化合物をエステル化反応することにより得られたテトラヒドロフタレートを過酸化物の存在下エポキシ化する方法等により得る事が出来る。 The epoxy compound can be obtained by a method of epoxidizing tetrahydrophthalate obtained by esterifying a tetrahydrophthalic anhydride and an alcohol compound in the presence of a peroxide.
上記一般式（１）においてＲ２が、Ａ群から選ばれるエポキシ化合物を得ようとした場合、その製造時アルコール化合物として炭素数１６〜２２の不飽和アルコールを用いる。該不飽和アルコール中の二重結合の数は１個以上であって、１〜３個が好ましい。 In the above general formula (1), when R 2 tries to obtain an epoxy compound selected from Group A, an unsaturated alcohol having 16 to 22 carbon atoms is used as an alcohol compound during the production. The number of double bonds in the unsaturated alcohol is 1 or more, preferably 1 to 3.
上記一般式（１）においてＲ２が、B群から選ばれるエポキシ化合物を得ようとした場合、その製造時アルコール化合物として炭素数１６〜２２の不飽和アルコールと飽和アルコールを併用して用いる。該不飽和アルコール中の二重結合の数は１個以上であって、１〜３個が好ましい。 In the above general formula (1), when R 2 tries to obtain an epoxy compound selected from Group B, an unsaturated alcohol having 16 to 22 carbon atoms and a saturated alcohol are used in combination as an alcohol compound during the production. The number of double bonds in the unsaturated alcohol is 1 or more, preferably 1 to 3.
上記製造方法で製造されるエポキシ化合物の酸価は通常２ｍｇＫＯＨ／ｇ以下であって、１ｍｇＫＯＨ／ｇ以下であることが好ましい。酸価が２ｍｇＫＯＨ／ｇより高いときは自身の酸価による加水分解が懸念される。 The acid value of the epoxy compound produced by the above production method is usually 2 mgKOH / g or less, and preferably 1 mgKOH / g or less. When the acid value is higher than 2 mgKOH / g, there is a concern about hydrolysis due to its own acid value.
上記、エポキシ化合物としては、
９−セチル，１０−エポキシセチル−４，５−エポキシヘキサヒドロフタレート、９−ステアリル，１０−エポキシセチル−４，５−エポキシヘキサヒドロフタレート、９−アラキル，１０−エポキシセチル−４，５−エポキシヘキサヒドロフタレート、９−ベヘニル，１０−エポキシセチル−４，５−エポキシヘキサヒドロフタレート、９−セチル，１０−エポキシステアリル−４，５−エポキシヘキサヒドロフタレート、９−ステアリル，１０−エポキシステアリル−４，５−エポキシヘキサヒドロフタレート、９−アラキル，１０−エポキシステアリル−４，５−エポキシヘキサヒドロフタレート、９−ベヘニル，１０−エポキシステアリル−４，５−エポキシヘキサヒドロフタレート、９−セチル，１０−エポキシアラキル−４，５−エポキシヘキサヒドロフタレート、９−ステアリル，１０−エポキシアラキル−４，５−エポキシヘキサヒドロフタレート、９−アラキル，１０−エポキシアラキル−４，５−エポキシヘキサヒドロフタレート、９−ベヘニル，１０−エポキシアラキル−４，５−エポキシヘキサヒドロフタレート、９−セチル，１０−エポキシベヘニル−４，５−エポキシヘキサヒドロフタレート、９−ステアリル，１０−エポキシベヘニル−４，５−エポキシヘキサヒドロフタレート、９−アラキル，１０−エポキシベヘニル−４，５−エポキシヘキサヒドロフタレート、９−ベヘニル，１０−エポキシベヘニル−４，５−エポキシヘキサヒドロフタレート、ジ（９，１０−エポキシセチル）−４，５−エポキシヘキサヒドロフタレート、ジ（９，１０−エポキシステアリル）−４，５−エポキシヘキサヒドロフタレート、ジ（９，１０−エポキシアラキル）−４，５−エポキシヘキサヒドロフタレート、ジ（９，１０−エポキシベヘニル）−４，５−エポキシヘキサヒドロフタレートが例示される。
As the above epoxy compound,
9-cetyl, 10-epoxycetyl-4,5-epoxyhexahydrophthalate, 9-stearyl, 10-epoxycetyl-4,5-epoxyhexahydrophthalate, 9-aralkyl, 10-epoxycetyl-4,5-epoxy Hexahydrophthalate, 9-behenyl, 10-epoxycetyl-4,5-epoxyhexahydrophthalate, 9-cetyl, 10-epoxystearyl-4,5-epoxyhexahydrophthalate, 9-stearyl, 10-epoxystearyl-4 , 5-epoxyhexahydrophthalate, 9-aralkyl, 10-epoxystearyl-4,5-epoxyhexahydrophthalate, 9-behenyl, 10-epoxystearyl-4,5-epoxyhexahydrophthalate, 9-cetyl, 10- Epoxy Arakil-4,5 Epoxy hexahydrophthalate, 9-stearyl, 10-epoxy aralkyl-4,5-epoxy hexahydrophthalate, 9-aralkyl, 10-epoxy aralkyl-4,5-epoxy hexahydrophthalate, 9-behenyl, 10-epoxy Aralkyl-4,5-epoxyhexahydrophthalate, 9-cetyl, 10-epoxybehenyl-4,5-epoxyhexahydrophthalate, 9-stearyl, 10-epoxybehenyl-4,5-epoxyhexahydrophthalate, 9- Aralkyl, 10-epoxybehenyl-4,5-epoxyhexahydrophthalate, 9-behenyl, 10-epoxybehenyl-4,5-epoxyhexahydrophthalate, di (9,10-epoxycetyl) -4,5-epoxyhexa Hydrophthalate, di (9,10 Epoxystearyl) -4,5-epoxyhexahydrophthalate, di (9,10-epoxyaralkyl) -4,5-epoxyhexahydrophthalate, di (9,10-epoxybehenyl) -4,5-epoxyhexahydro Phthalate is exemplified.
[その他の添加剤]
本発明に係る金属加工用潤滑油組成物には、その性能を向上させるために本発明の効果を損なわない範囲で従来公知の各種添加剤を１種又は２種以上を適宜添加することが可能である。そのような添加剤として、無灰型分散剤、金属系清浄剤、流動点降下剤、防錆剤、消泡剤などが挙げられる。又、必要に応じて、耐摩耗剤・極圧剤、油性剤・摩擦調整剤、酸化防止剤、腐食防止剤などを添加しても良い。通常、好ましく適用される添加量（基油及びエポキシ化合物の合計量に対する添加剤の重量％）を上記各添加剤の具体例と共に示す。
[Other additives]
In order to improve the performance of the lubricating oil composition for metal working according to the present invention, one or more conventionally known various additives can be appropriately added within a range not impairing the effects of the present invention. It is. Examples of such additives include ashless dispersants, metal detergents, pour point depressants, rust inhibitors, and antifoaming agents. Moreover, you may add an antiwear agent, extreme pressure agent, an oiliness agent, a friction modifier, antioxidant, a corrosion inhibitor, etc. as needed. Usually, the addition amount (weight% of the additive with respect to the total amount of base oil and an epoxy compound) applied preferably is shown with the specific example of said each additive.
無灰型分散剤としては、ポリアルケニルコハク酸イミド、ポリアルケニルコハク酸アミド、ポリアルケニルベンジルアミン、ポリアルケニルコハク酸エステルのほかこれらをホウ素化合物で処理した誘導体などが例示され、その添加量としては２〜１０重量％が挙げられる。 Examples of ashless dispersants include polyalkenyl succinimides, polyalkenyl succinic amides, polyalkenyl benzylamines, polyalkenyl succinic acid esters, and derivatives obtained by treating these with boron compounds. 2 to 10 weight% is mentioned.
金属系清浄剤としては、金属スルホネート、過塩基性金属スルホネート、金属フェネート、過塩基性金属フェネート、金属ホスホネート、サリシレート、カルボキシレートなどが例示され、その添加量としては２〜１０重量％が挙げられる。 Examples of metal detergents include metal sulfonates, overbased metal sulfonates, metal phenates, overbased metal phenates, metal phosphonates, salicylates, carboxylates, etc., and the addition amount is 2 to 10% by weight. .
流動点降下剤としては、ポリアルキルメタクリレート、ポリアルキルアクリレート、塩素化パラフィンとナフタレンの縮合物、塩素化パラフィンとフェノールの縮合物、ポリブテン、ポリアルキルスチレン、ポリビニルアセテートなどが例示され、その添加量としては０．１〜１重量％が挙げられる。 Examples of the pour point depressant include polyalkyl methacrylate, polyalkyl acrylate, condensate of chlorinated paraffin and naphthalene, condensate of chlorinated paraffin and phenol, polybutene, polyalkyl styrene, polyvinyl acetate and the like. Is 0.1 to 1% by weight.
防錆剤としては、スルフォン酸塩系、カルボン酸系、有機アミン石けん系、ソルビタン部分エステル系の化合物が例示され、その添加量としては０．０５〜３重量％が挙げられる。 Examples of the rust preventive include sulfonate-based, carboxylic acid-based, organic amine soap-based, and sorbitan partial ester-based compounds, and the amount added is 0.05 to 3% by weight.
消泡剤としては、ポリジメチルシリコーンなどのシリコーン系化合物が例示され、その添加量としては１〜１００ｐｐｍが挙げられる。 Examples of the antifoaming agent include silicone-based compounds such as polydimethylsilicone, and the amount added is 1 to 100 ppm.
耐摩耗剤・極圧剤としては、オレフィンポリサルファイド、硫化油脂、ジアルキルポリサルファイドなどの有機硫黄系、塩素化パラフィン、アルキル及びアリールりん酸エステル、アルキル及びアリール亜りん酸エステルなどの有機リン系、ジアルキルジチオリン酸亜鉛系、ジアルキルジチオカルバミン酸亜鉛系、長鎖脂肪酸系の化合物が例示され、その添加量としては０．０５〜１０重量％が挙げられる。 Antiwear / extreme pressure agents include organic sulfurs such as olefin polysulfides, sulfurized fats and oils, dialkyl polysulfides, chlorinated paraffins, organophosphorous compounds such as alkyl and aryl phosphites, alkyl and aryl phosphites, and dialkyldithiophosphorus. Zinc acid type, zinc dialkyldithiocarbamate type, and long chain fatty acid type compounds are exemplified, and the addition amount is 0.05 to 10% by weight.
油性剤・摩擦調整剤としては、ステアリン酸、オレイン酸などの脂肪酸類、ステアリルアルコール、オレイルアルコールなどのアルコール類、オレイルアミンなどのアミン類、モリブデンジチオカーバメートなどの有機モリブデン類が例示され、その添加量としては０．１〜５．０重量％が挙げられる。 Examples of oiliness agents and friction modifiers include fatty acids such as stearic acid and oleic acid, alcohols such as stearyl alcohol and oleyl alcohol, amines such as oleylamine, and organic molybdenum such as molybdenum dithiocarbamate. As 0.1 to 5.0% by weight.
酸化防止剤としては、２，６−ジ−ｔ−ブチルパラクレゾール、４，４’−メチレンビス（２，６−ジ−ｔ−ブチルフェノール）、４，４’−ビス（２，６−ジ−ｔ−ブチルフェノール）、４，４’−ビス（２−メチル−６−ｔ−ブチルフェノール）、２，２’−メチレンビス（４−エチル−６−ｔ−ブチルフェノール）、２，２’−メチレンビス（４−メチル−６−ｔ−ブチルフェノール）、４，４’−ブチリデンビス（３−メチル−６−ｔ−ブチルフェノール）、４，４’−チオビス（２−メチル−ｔ−ブチルフェノール）などのフェノール系酸化防止剤、Ｎ−フェニル−α−ナフチルアミン、Ｎ−オクチルフェニル−α−ナフチルアミン、ｐ，ｐ’−ジオクチルジフェニルアミンなどのアルキル化ジフェニルアミン、パラフェニレンジアミンなどのアミン系酸化防止剤、ジ−ｔ−ブチルフェニルホスファイト、トリフェニルホスフォロチオネート、アルキル化トリフェニルホスフォロチオネートなどのリン系酸化防止剤、フェノチアジン、硫化油脂、ジベンジルジサルファイド、ジセチルサルファイドなどの硫黄系酸化防止剤が挙げられる。 Antioxidants include 2,6-di-t-butylparacresol, 4,4′-methylenebis (2,6-di-t-butylphenol), 4,4′-bis (2,6-di-t). -Butylphenol), 4,4'-bis (2-methyl-6-t-butylphenol), 2,2'-methylenebis (4-ethyl-6-t-butylphenol), 2,2'-methylenebis (4-methyl) Phenolic antioxidants such as -6-tert-butylphenol), 4,4'-butylidenebis (3-methyl-6-tert-butylphenol), 4,4'-thiobis (2-methyl-tert-butylphenol), N -Alkylated diphenylamines such as phenyl-α-naphthylamine, N-octylphenyl-α-naphthylamine, p, p'-dioctyldiphenylamine, paraphenylenedia Amine-based antioxidants such as min, phosphorus-based antioxidants such as di-t-butylphenyl phosphite, triphenylphosphorothionate, alkylated triphenylphosphorothionate, phenothiazine, sulfurized fats and oils, dibenzyl disulfide And sulfur-based antioxidants such as dicetyl sulfide.
腐食防止剤としては、ベンゾトリアゾール、２，５−ビス（ｎ−ドデシルジチオ）−１，３，４−チアジアゾールなどのチアジアゾール系の化合物が例示され、その添加量としては０．０１〜０．４重量％が挙げられる。 Examples of the corrosion inhibitor include thiadiazole compounds such as benzotriazole and 2,5-bis (n-dodecyldithio) -1,3,4-thiadiazole, and the addition amount thereof is 0.01 to 0.4. % By weight.
消泡剤としては、ポリジメチルシリコーンなどのシリコーン系化合物が例示され、その添加量としては１〜１００ｐｐｍが挙げられる。 Examples of the antifoaming agent include silicone-based compounds such as polydimethylsilicone, and the amount added is 1 to 100 ppm.
以下に実施例を掲げて本発明を詳しく説明するが、本発明は実施例に限定されるものではない。尚、性能については以下の方法により評価した。 Hereinafter, the present invention will be described in detail with reference to examples, but the present invention is not limited to the examples. The performance was evaluated by the following method.
摩耗防止性能試験
荷重を標準条件の４０ｋｇｆから３０ｋｇｆに変更した以外は、ＪＰＩ−５Ｓ−３２−９０（社団法人日本石油学会：潤滑油の耐摩耗性試験方法(シェル四球式)）に準拠して、高速四球型摩耗試験機（神鋼造機製）を用いて、回転数１２００ｒｐｍ、荷重３０ｋｇｆ、時間６０分の条件で試験し、摩耗痕直径を測定した。摩耗痕の長短直径を測定、平均値を算出し摩耗痕直径とした。摩耗痕が小さいものほど潤滑性が良好とする。
According to JPI-5S-32-90 (Japan Petroleum Institute: Wear resistance test method of lubricant (shell four-ball type)) except that the wear prevention performance test load was changed from the standard condition of 40 kgf to 30 kgf. Using a high-speed four-ball wear tester (manufactured by Shinko Engineering Co., Ltd.), the test was performed under the conditions of a rotational speed of 1200 rpm, a load of 30 kgf, and a time of 60 minutes, and the wear scar diameter was measured. The long and short diameters of the wear marks were measured, and the average value was calculated as the wear mark diameter. The smaller the wear scar, the better the lubricity.
溶解性試験
攪拌装置を備えた１００ｍLのフラスコに、基油及びエポキシ化合物（基油/エポキシ化合物＝80/20、90/10）を５０ｍL入れ、充分攪拌したのち一時間静置した。静置後、目視で観察を行い基油とエポキシ化合物が分層するものを「×」と判定し、分層しないものを「○」と判定した。
50 mL of the base oil and the epoxy compound (base oil / epoxy compound = 80/20, 90/10) were put into a 100 mL flask equipped with a solubility test stirrer, and the mixture was sufficiently stirred and allowed to stand for 1 hour. After standing, it was visually observed to determine that the base oil and the epoxy compound were separated into “x”, and those that were not separated were judged as “◯”.
性能評価に用いた各試料の組成を表１及び２に示す。各実施例、比較例の成分は以下の通りである。 The composition of each sample used for performance evaluation is shown in Tables 1 and 2. The components of each example and comparative example are as follows.
［基油］
鉱油：パラフィン系鉱油（コスモ石油ルブリカンツ株式会社製 「コスモニュートラル１００」、１００℃の動粘度 ４．３ｍｍ２/s）
[Base oil]
Mineral oil: Paraffinic mineral oil (Cosmo Oil Lubricants Co., Ltd. “Cosmo Neutral 100”, kinematic viscosity at 100 ° C. 4.3 mm 2 / s)
［エポキシ化合物］
エポキシＡ：ジ（９，１０−エポキシステアリル）−４，５−エポキシヘキサヒドロフタレート
エポキシＢ：ジ（２−エチルヘキシル）−４，５−エポキシヘキサヒドロフタレート（商品名「サンソサイザーE−PS 新日本理化製）
エポキシＣ：ジ（ｎ−ヘキシル）−４，５−エポキシヘキサヒドロフタレート、ジ（ｎ−オクチル）−４，５−エポキシヘキサヒドロフタレート、ジ（ｎ−デシル）−４，５−エポキシヘキサヒドロフタレートの混合物（商品名「サンソサイザー ｎＥ−ＰＳ」、新日本理化製）
エポキシＤ：ｎ−ドデシルグリシジルエーテル、ｎ−テトラデシルグリシジルエーテルの混合物（商品名「リカレジン Ｌ−２００、新日本理化製」）
エポキシＥ：１，４−シクロヘキサンジメタノールグリシジルエーテル（商品名「リカレジン ＤＭＥ−１００ ）
エポキシＦ：ネオデカン酸グリシジルエステル（商品名「カージュラ Ｅ１０Ｐ」、ヘキシオン スペシャリティケミカルズ ジャパン社製）
エポキシＧ：３，４−エポキシシクロヘキセニルメチル−３’，４’−エポキシシクロヘキセンカルボキシレート（ダイセル化学工業株式会社製）
エポキシＨ：エポキシ化大豆油（商品名「サンソサイザー Ｅ−２０００Ｈ」、新日本理化製）
[Epoxy compound]
Epoxy A: Di (9,10-epoxystearyl) -4,5-epoxyhexahydrophthalate Epoxy B: Di (2-ethylhexyl) -4,5-epoxyhexahydrophthalate (trade name “Sanso Sizer E-PS Shin Nippon Rika)
Epoxy C: di (n-hexyl) -4,5-epoxyhexahydrophthalate, di (n-octyl) -4,5-epoxyhexahydrophthalate, di (n-decyl) -4,5-epoxyhexahydrophthalate Mixture (trade name “Sanso Sizer nE-PS”, manufactured by Shin Nippon Chemical Co., Ltd.)
Epoxy D: Mixture of n-dodecyl glycidyl ether and n-tetradecyl glycidyl ether (trade name “Rikaresin L-200, manufactured by Shin Nippon Rika”)
Epoxy E: 1,4-cyclohexanedimethanol glycidyl ether (trade name “Rica Resin DME-100”)
Epoxy F: glycidyl neodecanoate (trade name “Cardura E10P”, manufactured by Hexion Specialty Chemicals Japan)
Epoxy G: 3,4-epoxycyclohexenylmethyl-3 ′, 4′-epoxycyclohexene carboxylate (manufactured by Daicel Chemical Industries, Ltd.)
Epoxy H: Epoxidized soybean oil (trade name “Sansosizer E-2000H”, manufactured by Shin Nippon Rika)
実施例１〜２
表１及び表２に示す組成の試料油に対し摩耗防止性能試験及び溶解性試験を行った。得られた結果を表１及び表２に記載する。
Examples 1-2
Abrasion prevention performance test and solubility test were performed on sample oils having the compositions shown in Tables 1 and 2. The obtained results are shown in Tables 1 and 2.
比較例１〜１４
表１及び表２に示す組成の試料油に対し摩耗防止性能試験及び溶解性試験を行った。得られた結果を表１及び表２に併記する。
Comparative Examples 1-14
Abrasion prevention performance test and solubility test were performed on sample oils having the compositions shown in Tables 1 and 2. The obtained results are also shown in Tables 1 and 2.
本発明の特定の構造を有するエポキシ化合物を含有する潤滑油組成物は、耐摩耗性に優れエポキシ化合物の基油への溶解性も良好であることから、金属加工油として有用である。 The lubricating oil composition containing an epoxy compound having a specific structure of the present invention is useful as a metal working oil because it has excellent wear resistance and good solubility of the epoxy compound in the base oil.
Claims (4)
Ａ：炭素数１６〜２２のエポキシ基を有する飽和脂肪族炭化水素基
Ｂ：炭素数１６〜２２の飽和脂肪族炭化水素基]
で表される少なくとも１種のエポキシ化合物を含有してなる金属加工用潤滑油組成物。 At least one base oil selected from the group consisting of mineral oil, animal and vegetable oils and synthetic oils, and general formula (1)
A: Saturated aliphatic hydrocarbon group having an epoxy group having 16 to 22 carbon atoms B: Saturated aliphatic hydrocarbon group having 16 to 22 carbon atoms]
A lubricating oil composition for metal working comprising at least one epoxy compound represented by the formula:
Ａ：炭素数１６〜２２のエポキシ基を有する飽和脂肪族炭化水素基
Ｂ：炭素数１６〜２２の飽和脂肪族炭化水素基]
で表される少なくとも１種のエポキシ化合物を含有せしめることを特徴とする、金属加工用潤滑油組成物の摩耗防止性能向上方法。 General formula (1)
A: Saturated aliphatic hydrocarbon group having an epoxy group having 16 to 22 carbon atoms B: Saturated aliphatic hydrocarbon group having 16 to 22 carbon atoms]
A method for improving the anti-wear performance of a lubricating oil composition for metal working, which comprises containing at least one epoxy compound represented by the formula:
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| US8486873B2 (en) | 2010-03-31 | 2013-07-16 | Chevron Oronite Company Llc | Lubricating oil compositions containing epoxide antiwear agents |
| JP5683330B2 (en) * | 2011-03-07 | 2015-03-11 | ユシロ化学工業株式会社 | Water-soluble metalworking fluid composition |
| WO2018180548A1 (en) * | 2017-03-29 | 2018-10-04 | 東レ株式会社 | Photosensitive composition, cured film and organic el display device |
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| JPH11335688A (en) * | 1998-05-26 | 1999-12-07 | New Japan Chem Co Ltd | Lubricating oil composition |
| JP3945024B2 (en) * | 1998-06-23 | 2007-07-18 | 新日本理化株式会社 | 2-cycle engine oil composition |
| JP5071999B2 (en) * | 2005-03-23 | 2012-11-14 | Ｊｘ日鉱日石エネルギー株式会社 | Lubricating oil composition for metal working |
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