JPH028640B2 - - Google Patents
Info
- Publication number
- JPH028640B2 JPH028640B2 JP17711082A JP17711082A JPH028640B2 JP H028640 B2 JPH028640 B2 JP H028640B2 JP 17711082 A JP17711082 A JP 17711082A JP 17711082 A JP17711082 A JP 17711082A JP H028640 B2 JPH028640 B2 JP H028640B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- lubricating oil
- hydrocarbon group
- weight
- oil composition
- 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.)
- Expired
Links
- 239000000203 mixture Substances 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 16
- 239000010687 lubricating oil Substances 0.000 claims description 16
- 239000003963 antioxidant agent Substances 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 230000003078 antioxidant effect Effects 0.000 claims description 10
- 150000002430 hydrocarbons Chemical class 0.000 claims description 10
- 150000004982 aromatic amines Chemical class 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052725 zinc Inorganic materials 0.000 claims description 4
- 239000011701 zinc Substances 0.000 claims description 4
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 7
- VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 claims 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 7
- 229920000570 polyether Polymers 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- -1 trimethylopropane Chemical compound 0.000 description 5
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 229920001451 polypropylene glycol Polymers 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000314 lubricant Substances 0.000 description 3
- GSGDTSDELPUTKU-UHFFFAOYSA-N nonoxybenzene Chemical compound CCCCCCCCCOC1=CC=CC=C1 GSGDTSDELPUTKU-UHFFFAOYSA-N 0.000 description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- OOCCDEMITAIZTP-QPJJXVBHSA-N (E)-cinnamyl alcohol Chemical compound OC\C=C\C1=CC=CC=C1 OOCCDEMITAIZTP-QPJJXVBHSA-N 0.000 description 2
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 2
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- 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 2
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-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
- BTZVDPWKGXMQFW-UHFFFAOYSA-N Pentadecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCCCC(O)=O BTZVDPWKGXMQFW-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-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
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 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
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 239000010696 ester oil Substances 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- GOQYKNQRPGWPLP-UHFFFAOYSA-N heptadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 2
- QQHJDPROMQRDLA-UHFFFAOYSA-N hexadecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCCCCC(O)=O QQHJDPROMQRDLA-UHFFFAOYSA-N 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
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- JJOJFIHJIRWASH-UHFFFAOYSA-N icosanedioic acid Chemical compound OC(=O)CCCCCCCCCCCCCCCCCCC(O)=O JJOJFIHJIRWASH-UHFFFAOYSA-N 0.000 description 2
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 2
- ISYWECDDZWTKFF-UHFFFAOYSA-N nonadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCCC(O)=O ISYWECDDZWTKFF-UHFFFAOYSA-N 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
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 2
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- BNJOQKFENDDGSC-UHFFFAOYSA-N octadecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCCCCCCC(O)=O BNJOQKFENDDGSC-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
- REIUXOLGHVXAEO-UHFFFAOYSA-N pentadecan-1-ol Chemical compound CCCCCCCCCCCCCCCO REIUXOLGHVXAEO-UHFFFAOYSA-N 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
- 239000012264 purified product Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000010802 sludge Substances 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- SZHOJFHSIKHZHA-UHFFFAOYSA-N tridecanoic acid Chemical compound CCCCCCCCCCCCC(O)=O SZHOJFHSIKHZHA-UHFFFAOYSA-N 0.000 description 2
- LWBHHRRTOZQPDM-UHFFFAOYSA-N undecanedioic acid Chemical compound OC(=O)CCCCCCCCCC(O)=O LWBHHRRTOZQPDM-UHFFFAOYSA-N 0.000 description 2
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 description 1
- CFDRQRFAQCJPBZ-UHFFFAOYSA-N 1-chlorohexan-1-ol Chemical compound CCCCCC(O)Cl CFDRQRFAQCJPBZ-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- VETPHHXZEJAYOB-UHFFFAOYSA-N 1-n,4-n-dinaphthalen-2-ylbenzene-1,4-diamine Chemical compound C1=CC=CC2=CC(NC=3C=CC(NC=4C=C5C=CC=CC5=CC=4)=CC=3)=CC=C21 VETPHHXZEJAYOB-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
- QFGCFKJIPBRJGM-UHFFFAOYSA-N 12-[(2-methylpropan-2-yl)oxy]-12-oxododecanoic acid Chemical compound CC(C)(C)OC(=O)CCCCCCCCCCC(O)=O QFGCFKJIPBRJGM-UHFFFAOYSA-N 0.000 description 1
- RWLALWYNXFYRGW-UHFFFAOYSA-N 2-Ethyl-1,3-hexanediol Chemical compound CCCC(O)C(CC)CO RWLALWYNXFYRGW-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 235000021357 Behenic acid Nutrition 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-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
- GZZPOFFXKUVNSW-UHFFFAOYSA-N Dodecenoic acid Natural products OC(=O)CCCCCCCCCC=C GZZPOFFXKUVNSW-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- UTGQNNCQYDRXCH-UHFFFAOYSA-N N,N'-diphenyl-1,4-phenylenediamine Chemical compound C=1C=C(NC=2C=CC=CC=2)C=CC=1NC1=CC=CC=C1 UTGQNNCQYDRXCH-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 239000005643 Pelargonic acid Substances 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- OOCCDEMITAIZTP-UHFFFAOYSA-N allylic benzylic alcohol Natural products OCC=CC1=CC=CC=C1 OOCCDEMITAIZTP-UHFFFAOYSA-N 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 229940116226 behenic acid Drugs 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 229940093476 ethylene glycol Drugs 0.000 description 1
- 229960005082 etohexadiol Drugs 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000012208 gear oil Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229960005150 glycerol Drugs 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 1
- 229940051250 hexylene glycol Drugs 0.000 description 1
- 239000010720 hydraulic oil Substances 0.000 description 1
- ZSSIYIZVIFNDRJ-UHFFFAOYSA-N hydroxy-phenoxy-phenylsulfanyl-sulfanylidene-lambda5-phosphane Chemical compound C=1C=CC=CC=1SP(=S)(O)OC1=CC=CC=C1 ZSSIYIZVIFNDRJ-UHFFFAOYSA-N 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
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- CWQXQMHSOZUFJS-UHFFFAOYSA-N molybdenum disulfide Chemical compound S=[Mo]=S CWQXQMHSOZUFJS-UHFFFAOYSA-N 0.000 description 1
- 229910052982 molybdenum disulfide Inorganic materials 0.000 description 1
- XGFDHKJUZCCPKQ-UHFFFAOYSA-N n-nonadecyl alcohol Natural products CCCCCCCCCCCCCCCCCCCO XGFDHKJUZCCPKQ-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 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
- 239000003921 oil Substances 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
- 239000007800 oxidant agent Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 229960004063 propylene glycol Drugs 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- KJIOQYGWTQBHNH-UHFFFAOYSA-N undecanol Chemical compound CCCCCCCCCCCO KJIOQYGWTQBHNH-UHFFFAOYSA-N 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- ZNCAMSISVWKWHL-UHFFFAOYSA-L zinc;butoxy-butylsulfanyl-oxido-sulfanylidene-$l^{5}-phosphane Chemical compound [Zn+2].CCCCOP([O-])(=S)SCCCC.CCCCOP([O-])(=S)SCCCC ZNCAMSISVWKWHL-UHFFFAOYSA-L 0.000 description 1
- ZBDJNBFTEIUHPK-UHFFFAOYSA-L zinc;dihexoxy-sulfanylidene-sulfido-$l^{5}-phosphane Chemical compound [Zn+2].CCCCCCOP([S-])(=S)OCCCCCC.CCCCCCOP([S-])(=S)OCCCCCC ZBDJNBFTEIUHPK-UHFFFAOYSA-L 0.000 description 1
- GBEDXBRGRSPHRI-UHFFFAOYSA-L zinc;octoxy-octylsulfanyl-oxido-sulfanylidene-$l^{5}-phosphane Chemical compound [Zn+2].CCCCCCCCOP([O-])(=S)SCCCCCCCC.CCCCCCCCOP([O-])(=S)SCCCCCCCC GBEDXBRGRSPHRI-UHFFFAOYSA-L 0.000 description 1
- LZVDFWITYZHIEU-UHFFFAOYSA-L zinc;oxido-propoxy-propylsulfanyl-sulfanylidene-$l^{5}-phosphane Chemical compound [Zn+2].CCCOP([O-])(=S)SCCC.CCCOP([O-])(=S)SCCC LZVDFWITYZHIEU-UHFFFAOYSA-L 0.000 description 1
Landscapes
- Lubricants (AREA)
Description
この発明はポリエーテル系の潤滑油組成物、特
に高温安定性に優れた潤滑油組成物に関するもの
である。
ポリエーテル系化合物は粘度特性および潤滑性
に優れ、熱分解してもスラツジやワニスを生成せ
ず、また低流動点であり、金属やシール剤に対す
る影響が少なく、さらに化学的にも安定であるこ
とから、合成潤滑油基剤として優れており、広範
囲な分野に使用されている。しかしながらポリエ
ーテル系化合物は他の潤滑油基剤、例えば鉱物
油、燐酸エステル油、エステル油等に比較し高温
下における安定性が悪く、この欠点を改良するた
めに酸化防止剤を配合したり、新たな酸化防止剤
を見つけ出す試みがなされている。しかしこれら
の方法によつても、ポリエーテル化合物の分解温
度を20〜40℃上昇させるのが限度であり、高温用
潤滑油としてポリエーテル系化合物を用いること
は、特別の場合を除き不適当なものであつた。
本発明は上記のような従来の問題点を改善する
ためのもので、特定の構造をもつポリエーテル化
合物に抗酸化剤を配合することにより、優れた高
温安定性を示す潤滑油組成物を提供することを目
的としている。
この発明は下記〔〕式または〔〕式で示さ
れる化合物の１種または２種以上を90ないし99.9
重量％、ならびに抗酸化剤を0.1ないし10重量％
含有する潤滑油組成物である。
（ここで、R1は炭素数１ないし28で１価の炭化
水素基、R2は炭素数１ないし26で２価の炭化水
素基、R3は炭素数１ないし28でｂ価の炭化水素
基、R4は炭素数１ないし27で１価の炭化水素基、
ｍは２ないし４の整数、ａは炭素数２ないし４の
アルキレンオキシドの平均付加モル数で２ないし
100、ｂは１ないし８の整数である。）
〔〕式および〔〕式において、R1または
R3で示される炭化水素基としては、メタノール、
エタノール、プロパノール、ブタノール、ペンタ
ノール、ヘキサノール、ヘプタノール、ノナノー
ル、デカノール、ウンデカノール、ドデカノー
ル、トリデカノール、テトラデカノール、ペンタ
デカノール、ヘキサデカノール、ヘプタデカノー
ル、オクタデカノール、ノナデカノール、シクロ
ペンタノール、シクロロヘキサノール、ベンジル
アルコール、シンナミルアルコール、オレイルア
ルコール、エチレングリコール、プロピレングリ
コール、ヘキシレングリコール、オクチレングリ
コール、グリセリン、トリメチロプロパン、ペン
タエリスリトール、ソルビトール、ビスフエノー
ルＡ、ブチルフエノール、オクチルフエノール、
ノニルフエノール等の炭素数１〜28で１価ないし
８価のアルコール類またはフエノール類からOH
基を除いた炭化水素基が例示できるが、特にアル
キルフエノールからOH基を除いた炭化水素基が
好ましい。
R2またはR4で表わされる炭化水素基としては、
プロピオン酸、酪酸、吉草酸、カプロン酸、ペラ
ルゴン酸、カプリン酸、ウンデカン酸、ラウリン
酸、トリデカン酸、ミリスチン酸、ペンタデカン
酸、パルミチン酸、ステアリン酸、ノナデカン
酸、アラキジン酸、ベヘニン酸、クロトン酸、ド
デセン酸、オレイン酸、マロン酸、コハク酸、グ
ルタル酸、アジピン酸、ピメリン酸、スベリン
酸、アゼライン酸、セバシン酸、ウンデカン二
酸、ドデカン二酸、トデカン二酸、ペンタデカン
二酸、ヘキサデカン二酸、オクタデカン二酸、ア
イコサン二酸、マイレン酸、フマル酸、安息香
酸、ヒドロキシ安息香酸、フタル酸、ダイマー酸
等の炭素数３〜28で１価または２価のカルボン酸
からCOOH基を除いた炭化水素基が例示できる。
（CmH2mO）で表わされるアルキレンオキシ
ドとしてはエチレンオキシド、プロピレンオキシ
ド、ブチレンオキシド、テトラヒドロフラン等が
あり、これらのうち１種だけが付加していてもよ
く、また２種以上が付加していてもよい。２種以
上付加する場合、ランダム付加でもブロツク付加
でもよく、またその比率は特に制限されず、この
場合ａは全体の平均付加モル数となる。ｂはR3
の価数に対応する数で、R3に直接結合する鎖の
数を示す。
〔〕式および〔〕式の化合物は、R1、R3
に対応する前記アルコール類もしくはフエノール
類に、炭素数２ないし４のアルキレンオキシドを
付加重合させ、これによつて生成するポリオキシ
アルキレングリコール化合物を、R2、R4に対応
する前記カルボン酸と酸触媒の存在下にエステル
化反応させるか、または前記カルボン酸のメタノ
ール、エタノール等低級アルコールエステルとエ
ステル交換反応させることによつて製造できる。
〔〕式および〔〕式において、アルキレン
オキシドの付加モル数が２ないし100に限定され
るのは、２モル未満では分子中に占めるエーテル
結合の数が少ないため、低温特性および粘度特性
が悪くなり、また100を越えると分子中に占める
エーテル結合の数が多くなり過ぎて、熱安定性が
低下するためである。
本発明において使用する抗酸化剤としては特に
制限はなく、例えばフエノール系、アリールアミ
ン系、アリールチオアミン系、カーバメイト系、
ジンクジアルジチオホスフエート（以下ZDTPと
記載する）系等の公知のものを含むあらゆる種類
のものが使用可能であるが、特にアリールアミン
系またはアリールチオアミン系とZDTP系とを組
合せたものが好ましい。
上記フエノール系の抗酸化剤としては、例えば
４，４′−チオビス−（６−ターシヤリーブチル−
３−メチルフエノール等がある。またアリールア
ミン系またはアリールチオアミン系の抗酸化剤の
例としては、Ｎ，N′−ジセカンダリ−ブチル−
ｐ−フエニレンジアミン、Ｎ−フエニル−α−ナ
フチルアミン、Ｎ，N′−ジフエニル−ｐ−フエ
ニレンジアミン、Ｎ，N′−ジ−β−ナフチル−
ｐ−フエニレンジアミン、Ｎ−フエニル−N′−
イソプロピル−ｐ−フエニルレンジアミン、フエ
ノチアジン等がある。さらにZDTP系の抗酸化剤
の例としては、ジンクメチルジチオホスフエー
ト、ジンクエチルジチオホスフエート、ジンクジ
プロピルジチオホスフエート、ジンクジブチルジ
チオホスフエート、ジンクジヘキシルジチオホス
フエート、ジンクジオクチルジチオホスフエー
ト、ジンクジフエニルジチオホスフエート等があ
る。
アリールアミン系またはアリールチオアミン系
とZDTP系の抗酸化剤とを併用する場合の両者の
使用比率は、アリールアミン系またはアリールチ
オアミン系の抗酸化剤が20〜80重量％、ZDTP系
の抗酸化剤が80〜20重量％とするのが好ましい。
本発明の潤滑油組成物〔〕式または〔〕式
で示される化合物の１種または２種以上を90〜
99.9重量％、抗酸化剤0.1〜10重量％を含有する
組成物であるが、必要により二硫化モリブデン、
グラフアイト、雲母等の固体潤滑剤をさらに0.1
〜10重量％配合して用いてもよい。さらに必要に
より公知の極圧剤、油性向上剤、防錆剤、消泡剤
等の各種添加剤を併用してもよい。
本発明の潤滑油組成物は熱媒体、高温用作動
油、高温用ギヤー油、高温用コンベアー油等にそ
の効果を最大限に発揮し、さらに作動油、金属加
工油、金属含浸油、エンジン油等にも使用でき
る。本発明の潤滑油組成物は特に高温用潤滑油と
して優れているが、中低温用としても使用可能で
ある。
本発明によれば、特定の構造をもつポリエーテ
ル化合物に抗酸化剤を配合するように構成したの
で、優れた高温安定性を示し、かつ流動点が低
く、優れた粘度特性および低温特性を示すという
効果が得られる。
以下実施例により本発明を説明する。
製造例 １
〔〕式化合物の製造
２の気密反応容器にノニルフエノール440ｇ
（２モル）、触媒として水酸化カリウム２ｇをと
り、窒素ガス雰囲気下でプロピレンオキシド1160
ｇ（20モル）を90〜130℃、0.5〜5.0Kg／cm2に加
圧下で重合させてポリオキシプロピレングリコー
ルモノノニルフエニルエーテル（粗反応物）1595
ｇを得た。この粗反応物中の水酸化カリウムを塩
酸水溶液で中和後、80〜120℃、50mmHg以下の減
圧下で２時間脱水し、析出した塩を別し精製反
応物1587ｇを得た。この精製反応物の分子量を末
端水酸基定量法により測定したところ798であつ
た。次に２容のフラスコに上記の精製したポリ
オキシブロピレングリコールモノノニルフエニル
エーテル798ｇ（１モル）、アジピン酸73ｇ（0.5
モル）、触媒としてパラトルエンスルホン酸２ｇ
を入れ、130〜180℃、50mmHg以下の減圧下でエ
ステル化反応を10時間行い、粗反応物860ｇを得
た。この粗反応物中の触媒を除去するためアルカ
リ水で２回水洗した後、80〜120℃、50mmHg以下
の減圧下で１時間脱水し、精製品（試料No.１）
800ｇを得た。
製造例 ２
〔〕式化合物の製造
３容のフラスコにポリプロピレングリコール
（平均分子量3000）1500ｇ（0.5モル）、オレイン
酸282ｇ（１モル）、触媒としてパラトルエンスル
ホン酸４ｇを入れ、130〜180℃、50mmHg以下の
減圧下で脱水反応を20時間実施し、粗反応物1740
ｇを得た。製造例１と同様の操作を行い、精製品
（試料No.２）1700ｇを得た。
製造例１および２と同様の方法で、以下の試験
例に記載した〔〕式および〔〕式の化合物を
製造した。
試験例 １
表１に示す組成の本発明品および比較品の潤滑
油組成物につき、粘度、粘度指数、流動点ならび
に熱安定性を測定した結果を表２に示す。表１
中、〔〕、〔〕はそれぞれ〔〕式または〔〕
式の化合物であることを示す。また表２中の熱安
定性の測定は熱天秤を用い、以下の測定条件で測
定した。
〔測定条件〕
サンプル量：20mg
測定雰囲気：窒素ガス気流中
測定温度：200℃（200℃の達するまでは20℃／
minで昇温）
分解開始時間：200℃に達してからサンプルが減
量を開始するまでの時間
50％分解時間：200℃に達してからサンプルの50
％が減量するまでの時間
表２の結果より、本発明品（No.１〜No.７）はNo.
12を除く比較品よりも熱安定性に優れていること
がわかる。また比較品No.12は熱安定性には優れて
いるが、本発明品に比較して粘度指数が小さい。
The present invention relates to polyether-based lubricating oil compositions, particularly to lubricating oil compositions with excellent high-temperature stability. Polyether compounds have excellent viscosity and lubricity, do not produce sludge or varnish when thermally decomposed, have a low pour point, have little effect on metals and sealants, and are chemically stable. Therefore, it is an excellent synthetic lubricant base and is used in a wide range of fields. However, polyether compounds have poor stability at high temperatures compared to other lubricating oil bases, such as mineral oils, phosphate ester oils, and ester oils. Attempts are being made to find new antioxidants. However, even with these methods, the limit is to raise the decomposition temperature of polyether compounds by 20 to 40°C, and using polyether compounds as high-temperature lubricants is inappropriate except in special cases. It was hot. The present invention aims to improve the conventional problems as described above, and provides a lubricating oil composition that exhibits excellent high-temperature stability by incorporating an antioxidant into a polyether compound having a specific structure. It is intended to. This invention relates to one or more compounds represented by the following formula [] or [] with 90 to 99.9
% by weight, as well as 0.1 to 10% by weight of antioxidants.
A lubricating oil composition containing (Here, R 1 is a monovalent hydrocarbon group having 1 to 28 carbon atoms, R 2 is a divalent hydrocarbon group having 1 to 26 carbon atoms, and R 3 is a b-valent hydrocarbon group having 1 to 28 carbon atoms. group, R 4 is a monovalent hydrocarbon group having 1 to 27 carbon atoms,
m is an integer of 2 to 4, a is the average number of moles added of alkylene oxide having 2 to 4 carbon atoms, and 2 to 4;
100, b is an integer from 1 to 8. ) In formulas [] and [], R 1 or
Hydrocarbon groups represented by R 3 include methanol,
Ethanol, propanol, butanol, pentanol, hexanol, heptanol, nonanol, decanol, undecanol, dodecanol, tridecanol, tetradecanol, pentadecanol, hexadecanol, heptadecanol, octadecanol, nonadecanol, cyclopentanol, Chlorohexanol, benzyl alcohol, cinnamyl alcohol, oleyl alcohol, ethylene glycol, propylene glycol, hexylene glycol, octylene glycol, glycerin, trimethylopropane, pentaerythritol, sorbitol, bisphenol A, butylphenol, octylphenol,
OH from monovalent to octavalent alcohols or phenols with 1 to 28 carbon atoms such as nonylphenol
Examples include hydrocarbon groups obtained by removing OH groups from alkylphenols, and particularly preferred are hydrocarbon groups obtained by removing OH groups from alkylphenols. The hydrocarbon group represented by R 2 or R 4 is
Propionic acid, butyric acid, valeric acid, caproic acid, pelargonic acid, capric acid, undecanoic acid, lauric acid, tridecanoic acid, myristic acid, pentadecanoic acid, palmitic acid, stearic acid, nonadecanoic acid, arachidic acid, behenic acid, crotonic acid, Dodecenoic acid, oleic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, undecanedioic acid, dodecanedioic acid, todecanedioic acid, pentadecanedioic acid, hexadecanedioic acid, Hydrocarbons obtained by removing the COOH group from monovalent or divalent carboxylic acids with 3 to 28 carbon atoms, such as octadecanedioic acid, icosanedioic acid, maleic acid, fumaric acid, benzoic acid, hydroxybenzoic acid, phthalic acid, and dimer acid. Examples include groups. Examples of the alkylene oxide represented by (CmH 2 mO) include ethylene oxide, propylene oxide, butylene oxide, tetrahydrofuran, etc. Only one type of these may be added, or two or more types may be added. . When two or more types are added, random addition or block addition may be used, and the ratio is not particularly limited. In this case, a is the overall average number of moles added. b is R3
The number corresponds to the valence of and indicates the number of chains directly bonded to R 3 . Compounds of formulas [] and [] have R 1 , R 3
An alkylene oxide having 2 to 4 carbon atoms is addition-polymerized to the alcohol or phenol corresponding to It can be produced by carrying out an esterification reaction in the presence of a catalyst, or by carrying out a transesterification reaction of the carboxylic acid with a lower alcohol ester such as methanol or ethanol. In formulas [] and [], the number of moles of alkylene oxide added is limited to 2 to 100 because if it is less than 2 moles, the number of ether bonds in the molecule is small, resulting in poor low-temperature properties and viscosity properties. , and if it exceeds 100, the number of ether bonds in the molecule becomes too large, resulting in a decrease in thermal stability. There are no particular limitations on the antioxidants used in the present invention, such as phenol-based, arylamine-based, arylthioamine-based, carbamate-based,
All kinds of compounds can be used, including known ones such as zinc dialdithiophosphate (hereinafter referred to as ZDTP), but arylamine compounds or a combination of arylthioamine and ZDTP compounds are particularly preferred. . Examples of the above-mentioned phenolic antioxidant include 4,4'-thiobis-(6-tert-butyl-
Examples include 3-methylphenol. Examples of arylamine-based or arylthioamine-based antioxidants include N,N'-dise-butyl-
p-phenylenediamine, N-phenyl-α-naphthylamine, N,N'-diphenyl-p-phenylenediamine, N,N'-di-β-naphthyl-
p-phenylenediamine, N-phenyl-N'-
Examples include isopropyl-p-phenyl diamine and phenothiazine. Furthermore, examples of ZDTP-based antioxidants include zinc methyl dithiophosphate, zinc ethyl dithiophosphate, zinc dipropyl dithiophosphate, zinc dibutyl dithiophosphate, zinc dihexyl dithiophosphate, zinc dioctyl dithiophosphate, zinc Examples include diphenyldithiophosphate. When using an arylamine or arylthioamine type antioxidant and a ZDTP type antioxidant, the ratio of both is 20 to 80% by weight of the arylamine or arylthioamine type antioxidant, and 20 to 80% by weight of the arylamine type or arylthioamine type antioxidant, and Preferably, the oxidizing agent is 80 to 20% by weight. The lubricating oil composition of the present invention contains one or more compounds represented by the formula [] or [].
The composition contains 99.9% by weight and 0.1 to 10% by weight of antioxidant, but if necessary, molybdenum disulfide,
Add 0.1 additional solid lubricant such as graphite, mica, etc.
It may be used in a blend of up to 10% by weight. Furthermore, if necessary, various additives such as known extreme pressure agents, oiliness improvers, rust preventives, antifoaming agents, etc. may be used in combination. The lubricating oil composition of the present invention exhibits its maximum effect on heat carriers, high-temperature hydraulic oils, high-temperature gear oils, high-temperature conveyor oils, etc.; It can also be used for The lubricating oil composition of the present invention is particularly excellent as a lubricating oil for high temperatures, but can also be used for medium to low temperatures. According to the present invention, since an antioxidant is blended into a polyether compound having a specific structure, it exhibits excellent high-temperature stability, a low pour point, and excellent viscosity characteristics and low-temperature characteristics. This effect can be obtained. The present invention will be explained below with reference to Examples. Production example 1 Production of compound of formula [] 440 g of nonylphenol was placed in the airtight reaction vessel of 2.
(2 mol), 2 g of potassium hydroxide as a catalyst, and propylene oxide 1160 in a nitrogen gas atmosphere.
Polyoxypropylene glycol monononyl phenyl ether (crude reactant) 1595 was obtained by polymerizing 20 moles of polyoxypropylene glycol monononyl phenyl ether (crude reactant) at 90-130°C and 0.5-5.0 Kg/ cm2 under pressure.
I got g. After neutralizing the potassium hydroxide in this crude reaction product with an aqueous hydrochloric acid solution, it was dehydrated for 2 hours at 80-120°C under a reduced pressure of 50 mmHg or less, and the precipitated salt was separated to obtain 1587 g of a purified reaction product. The molecular weight of this purified reaction product was determined to be 798 by the terminal hydroxyl group determination method. Next, 798 g (1 mol) of the purified polyoxypropylene glycol monononyl phenyl ether and 73 g (0.5 g) of adipic acid were placed in a 2-volume flask.
mole), 2 g of para-toluenesulfonic acid as catalyst
was added, and the esterification reaction was carried out at 130 to 180°C under reduced pressure of 50 mmHg or less for 10 hours to obtain 860 g of a crude reaction product. In order to remove the catalyst in this crude reaction product, it was washed twice with alkaline water, and then dehydrated for 1 hour at 80 to 120°C under reduced pressure of 50 mmHg or less, and the purified product (sample No. 1)
Obtained 800g. Production Example 2 Production of a compound of the formula [] 1500 g (0.5 mol) of polypropylene glycol (average molecular weight 3000), 282 g (1 mol) of oleic acid, and 4 g of paratoluenesulfonic acid as a catalyst were placed in a 3-volume flask, and heated at 130 to 180°C. The dehydration reaction was carried out under reduced pressure of 50 mmHg or less for 20 hours, and the crude reaction product was 1740
I got g. The same operation as in Production Example 1 was performed to obtain 1700 g of purified product (sample No. 2). Compounds of formulas [] and [] described in the following Test Examples were produced in the same manner as in Production Examples 1 and 2. Test Example 1 Table 2 shows the results of measuring the viscosity, viscosity index, pour point, and thermal stability of the lubricating oil compositions of the present invention and comparative products having the compositions shown in Table 1. Table 1
Inside, [], and [] are respectively [] expression or []
Indicates that the compound is of the formula. The thermal stability in Table 2 was measured using a thermobalance under the following measurement conditions. [Measurement conditions] Sample amount: 20mg Measurement atmosphere: Nitrogen gas flow Measurement temperature: 200℃ (20℃/20℃ until reaching 200℃)
Decomposition start time: 50% time from when the sample reaches 200℃ until the sample starts to lose weight 50% Decomposition time: 50% of the sample after reaching 200℃
From the results in Table 2, the products of the present invention (No. 1 to No. 7) are No. 1.
It can be seen that the thermal stability is superior to the comparative products except for No. 12. Comparative product No. 12 has excellent thermal stability, but has a lower viscosity index than the product of the present invention.
【表】【table】
【表】【table】
【表】【table】
【表】
試験例 ２
表１の試料No.１を用いて熱触媒としての性能評
価を実施した。性能評価はヒートセツター用の熱
媒体として、210℃、800時間（８時間／日）の試
験を行つた。結果を表３に示す。[Table] Test Example 2 Using sample No. 1 in Table 1, performance evaluation as a thermal catalyst was conducted. Performance evaluation was conducted as a heat medium for a heat setter at 210°C for 800 hours (8 hours/day). The results are shown in Table 3.
【表】
＊ 粘度比＝テスト後動粘度／テスト
前動粘度
表３の結果より、粘度および酸価の変化が少な
く、スラツジ等の発生も認められず、熱媒体とし
て優れていることがわかる。[Table] * Viscosity ratio = kinematic viscosity after test / kinematic viscosity before test From the results in Table 3, it can be seen that there is little change in viscosity and acid value, and no sludge is observed, indicating that it is excellent as a heat medium.
Claims (1)
物の１種または２種以上を90ないし99.9重量％な
らびに抗酸化剤を0.1ないし10重量％含有する潤
滑油組成物。 （ここで、R1は炭素水１ないし28で１価の炭化
水素基、R2は炭化水素１ないし26で２価の炭化
水素基、R3は炭素数１ないし28でｂ価の炭化水
素基、R4は炭化水素１ないし27で１価の炭化水
素基、ｍは２ないし４の整数、ａは炭素水２ない
し４のアルキレンオキシドの平均付加モル数で２
ないし100、ｂは１ないし８の整数である。） ２ R1およびR3がそれぞれアルコール類または
フエノール類からOH基を除いた炭化水素基であ
る特許請求の範囲第１項記載の潤滑油組成物。 ３ R1およびR3がそれぞれアルキルフエノール
からOH基を除いた炭化水素基である特許請求の
範囲第１項記載の潤滑油組成物。 ４ R2およR4がそれぞれカルボン酸からCOOH
基を除いた炭化水素基である特許請求の範囲第１
項ないし第３項のいずれかに記載の潤滑油組成
物。 ５ 抗酸化剤がフエノール系、アリールアミン
系、アリールチオアミン系、カーバメイト系、ま
たはジンクジアルジチオホスフエート系のもので
ある特許請求の範囲第１項ないし第４項のいずれ
かに記載の潤滑油組成物。 ６ 抗酸化剤がアリールアミン系またはアリール
チオアミン系のもの20ないし80重量％と、ジンク
ジアルキルジチオホスフエート系のものも20ない
し80重量％とからなるものである特許請求の範囲
第１項ないし第４項のいずれかに記載の潤滑油組
成物。[Claims] 1. A lubricating oil composition containing 90 to 99.9% by weight of one or more compounds represented by the following formula [] or [] and 0.1 to 10% by weight of an antioxidant. (Here, R 1 is a monovalent hydrocarbon group with 1 to 28 carbon atoms, R 2 is a divalent hydrocarbon group with 1 to 26 carbon atoms, and R 3 is a b-valent hydrocarbon group with 1 to 28 carbon atoms. group, R 4 is a monovalent hydrocarbon group with 1 to 27 hydrocarbons, m is an integer of 2 to 4, a is the average number of moles added of alkylene oxide of 2 to 4 carbon water, and 2
to 100, b is an integer from 1 to 8. 2. The lubricating oil composition according to claim 1, wherein R 1 and R 3 are each a hydrocarbon group obtained by removing an OH group from an alcohol or a phenol. 3. The lubricating oil composition according to claim 1, wherein R 1 and R 3 are each a hydrocarbon group obtained by removing an OH group from an alkylphenol. 4 R 2 and R 4 are each converted from carboxylic acid to COOH
Claim 1 which is a hydrocarbon group excluding the group
The lubricating oil composition according to any one of Items 1 to 3. 5. The lubricating oil according to any one of claims 1 to 4, wherein the antioxidant is phenolic, arylamine, arylthioamine, carbamate, or zinc dialdithiophosphate. Composition. 6. Claims 1 to 6, wherein the antioxidant consists of 20 to 80% by weight of an arylamine or arylthioamine, and 20 to 80% by weight of a zinc dialkyldithiophosphate. The lubricating oil composition according to any one of Item 4.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17711082A JPS5966495A (en) | 1982-10-08 | 1982-10-08 | Lubricant composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17711082A JPS5966495A (en) | 1982-10-08 | 1982-10-08 | Lubricant composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5966495A JPS5966495A (en) | 1984-04-14 |
| JPH028640B2 true JPH028640B2 (en) | 1990-02-26 |
Family
ID=16025325
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP17711082A Granted JPS5966495A (en) | 1982-10-08 | 1982-10-08 | Lubricant composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5966495A (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4994511A (en) * | 1987-09-14 | 1991-02-19 | Shell Oil Company | Polyketone stabilization with dihydrocarbyldithiocarbamate salts |
| JP2625007B2 (en) * | 1988-08-05 | 1997-06-25 | 花王株式会社 | Heat resistant synthetic lubricating oil |
| US4959169A (en) * | 1989-10-20 | 1990-09-25 | The Dow Chemical Company | Esterified polyglycol lubricants for refrigeration compressors |
| CN101410499A (en) * | 2006-03-30 | 2009-04-15 | 新日铁化学株式会社 | Lubricant base oil |
-
1982
- 1982-10-08 JP JP17711082A patent/JPS5966495A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5966495A (en) | 1984-04-14 |
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