JP5561880B2 - 内燃機関潤滑剤 - Google Patents
内燃機関潤滑剤 Download PDFInfo
- Publication number
- JP5561880B2 JP5561880B2 JP2012510850A JP2012510850A JP5561880B2 JP 5561880 B2 JP5561880 B2 JP 5561880B2 JP 2012510850 A JP2012510850 A JP 2012510850A JP 2012510850 A JP2012510850 A JP 2012510850A JP 5561880 B2 JP5561880 B2 JP 5561880B2
- Authority
- JP
- Japan
- Prior art keywords
- lubricating composition
- substituted
- malimide
- carbon atoms
- composition according
- 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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- 238000002485 combustion reaction Methods 0.000 title claims description 24
- 239000010705 motor oil Substances 0.000 title claims description 15
- 239000000203 mixture Substances 0.000 claims description 142
- 230000001050 lubricating effect Effects 0.000 claims description 86
- -1 amine salts Chemical class 0.000 claims description 58
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 48
- 125000004432 carbon atom Chemical group C* 0.000 claims description 32
- 239000002270 dispersing agent Substances 0.000 claims description 32
- 239000003921 oil Substances 0.000 claims description 26
- 238000005260 corrosion Methods 0.000 claims description 21
- 230000007797 corrosion Effects 0.000 claims description 21
- 150000001412 amines Chemical class 0.000 claims description 18
- 239000004034 viscosity adjusting agent Substances 0.000 claims description 17
- 239000003795 chemical substances by application Substances 0.000 claims description 16
- 239000000314 lubricant Substances 0.000 claims description 16
- 239000003599 detergent Substances 0.000 claims description 15
- 239000003607 modifier Substances 0.000 claims description 15
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 13
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 13
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 13
- 229910052698 phosphorus Inorganic materials 0.000 claims description 13
- 239000011574 phosphorus Substances 0.000 claims description 13
- 239000011593 sulfur Substances 0.000 claims description 13
- 239000003963 antioxidant agent Substances 0.000 claims description 12
- 239000005078 molybdenum compound Substances 0.000 claims description 12
- 150000002752 molybdenum compounds Chemical class 0.000 claims description 12
- 229910000831 Steel Inorganic materials 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 229910052742 iron Inorganic materials 0.000 claims description 6
- 239000010959 steel Substances 0.000 claims description 6
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 229910052750 molybdenum Inorganic materials 0.000 claims description 5
- 239000011733 molybdenum Substances 0.000 claims description 5
- KHYKFSXXGRUKRE-UHFFFAOYSA-J molybdenum(4+) tetracarbamodithioate Chemical class C(N)([S-])=S.[Mo+4].C(N)([S-])=S.C(N)([S-])=S.C(N)([S-])=S KHYKFSXXGRUKRE-UHFFFAOYSA-J 0.000 claims description 5
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 4
- 229940053200 antiepileptics fatty acid derivative Drugs 0.000 claims description 3
- 150000002194 fatty esters Chemical class 0.000 claims description 3
- 150000002462 imidazolines Chemical class 0.000 claims description 3
- 235000011007 phosphoric acid Nutrition 0.000 claims description 3
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 claims description 3
- 229960001860 salicylate Drugs 0.000 claims description 3
- 150000002118 epoxides Chemical class 0.000 claims 1
- 235000019198 oils Nutrition 0.000 description 25
- 238000006243 chemical reaction Methods 0.000 description 18
- 239000000654 additive Substances 0.000 description 16
- 229920000768 polyamine Polymers 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 239000000446 fuel Substances 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 12
- 150000002148 esters Chemical class 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 11
- 239000000047 product Substances 0.000 description 10
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 8
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 7
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 7
- 230000003078 antioxidant effect Effects 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 7
- 229920001577 copolymer Polymers 0.000 description 7
- 239000003112 inhibitor Substances 0.000 description 7
- 239000001630 malic acid Substances 0.000 description 7
- 235000011090 malic acid Nutrition 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 125000001931 aliphatic group Chemical group 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 229960002317 succinimide Drugs 0.000 description 6
- 150000001336 alkenes Chemical class 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 230000005540 biological transmission Effects 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 4
- 239000005977 Ethylene Substances 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 150000002924 oxiranes Chemical class 0.000 description 4
- 150000003141 primary amines Chemical class 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 229910000838 Al alloy Inorganic materials 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000002518 antifoaming agent Substances 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 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 3
- 239000012530 fluid Substances 0.000 description 3
- 239000003502 gasoline Substances 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- 235000021317 phosphate Nutrition 0.000 description 3
- 229920000193 polymethacrylate Polymers 0.000 description 3
- 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 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 239000003760 tallow Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 2
- CJBDUOMQLFKVQC-UHFFFAOYSA-N 3-(2-hydroxyphenyl)propanoic acid Chemical compound OC(=O)CCC1=CC=CC=C1O CJBDUOMQLFKVQC-UHFFFAOYSA-N 0.000 description 2
- BKJVCQRVIQKQHD-UHFFFAOYSA-N 3-dodecyl-3-hydroxypyrrolidine-2,5-dione Chemical class CCCCCCCCCCCCC1(O)CC(=O)NC1=O BKJVCQRVIQKQHD-UHFFFAOYSA-N 0.000 description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 229920002367 Polyisobutene Polymers 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 239000002585 base Substances 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
- 150000001721 carbon Chemical group 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- 238000010531 catalytic reduction reaction Methods 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 150000001860 citric acid derivatives Chemical class 0.000 description 2
- 239000012459 cleaning agent Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 230000001627 detrimental effect Effects 0.000 description 2
- 239000002283 diesel fuel Substances 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000013020 final formulation Substances 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000010687 lubricating oil Substances 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 2
- NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical compound OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 229920002401 polyacrylamide Polymers 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 150000003873 salicylate salts Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000003871 sulfonates Chemical class 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-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
- BIGYLAKFCGVRAN-UHFFFAOYSA-N 1,3,4-thiadiazolidine-2,5-dithione Chemical compound S=C1NNC(=S)S1 BIGYLAKFCGVRAN-UHFFFAOYSA-N 0.000 description 1
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 1
- RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- IHWDSEPNZDYMNF-UHFFFAOYSA-N 1H-indol-2-amine Chemical compound C1=CC=C2NC(N)=CC2=C1 IHWDSEPNZDYMNF-UHFFFAOYSA-N 0.000 description 1
- QLSWIGRIBOSFMV-UHFFFAOYSA-N 1h-pyrrol-2-amine Chemical compound NC1=CC=CN1 QLSWIGRIBOSFMV-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- QVXGKJYMVLJYCL-UHFFFAOYSA-N 2,3-di(nonyl)-N-phenylaniline Chemical compound C(CCCCCCCC)C=1C(=C(C=CC1)NC1=CC=CC=C1)CCCCCCCCC QVXGKJYMVLJYCL-UHFFFAOYSA-N 0.000 description 1
- BVUXDWXKPROUDO-UHFFFAOYSA-N 2,6-di-tert-butyl-4-ethylphenol Chemical compound CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 BVUXDWXKPROUDO-UHFFFAOYSA-N 0.000 description 1
- DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 description 1
- SZATXRHXOOLEFV-UHFFFAOYSA-N 2,6-ditert-butyl-4-dodecylphenol Chemical compound CCCCCCCCCCCCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SZATXRHXOOLEFV-UHFFFAOYSA-N 0.000 description 1
- STHGHFNAPPFPQV-UHFFFAOYSA-N 2,6-ditert-butyl-4-propylphenol Chemical compound CCCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 STHGHFNAPPFPQV-UHFFFAOYSA-N 0.000 description 1
- QDCPNGVVOWVKJG-VAWYXSNFSA-N 2-[(e)-dodec-1-enyl]butanedioic acid Chemical compound CCCCCCCCCC\C=C\C(C(O)=O)CC(O)=O QDCPNGVVOWVKJG-VAWYXSNFSA-N 0.000 description 1
- BOBATFKNMFWLFG-UHFFFAOYSA-N 2-amino-2-cyano-n-methylacetamide Chemical compound CNC(=O)C(N)C#N BOBATFKNMFWLFG-UHFFFAOYSA-N 0.000 description 1
- JWYUFVNJZUSCSM-UHFFFAOYSA-N 2-aminobenzimidazole Chemical compound C1=CC=C2NC(N)=NC2=C1 JWYUFVNJZUSCSM-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- WVRNUXJQQFPNMN-VAWYXSNFSA-N 3-[(e)-dodec-1-enyl]oxolane-2,5-dione Chemical compound CCCCCCCCCC\C=C\C1CC(=O)OC1=O WVRNUXJQQFPNMN-VAWYXSNFSA-N 0.000 description 1
- WTWGHNZAQVTLSQ-UHFFFAOYSA-N 4-butyl-2,6-ditert-butylphenol Chemical compound CCCCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 WTWGHNZAQVTLSQ-UHFFFAOYSA-N 0.000 description 1
- CMGDVUCDZOBDNL-UHFFFAOYSA-N 4-methyl-2h-benzotriazole Chemical compound CC1=CC=CC2=NNN=C12 CMGDVUCDZOBDNL-UHFFFAOYSA-N 0.000 description 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
- IWHLYPDWHHPVAA-UHFFFAOYSA-N 6-hydroxyhexanoic acid Chemical compound OCCCCCC(O)=O IWHLYPDWHHPVAA-UHFFFAOYSA-N 0.000 description 1
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- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
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- 239000005642 Oleic acid Substances 0.000 description 1
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- GLOYGJPNNKTDIG-UHFFFAOYSA-N SC=1N=NSC=1S Chemical class SC=1N=NSC=1S GLOYGJPNNKTDIG-UHFFFAOYSA-N 0.000 description 1
- 229920000147 Styrene maleic anhydride Polymers 0.000 description 1
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- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 125000005233 alkylalcohol group Chemical group 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000005005 aminopyrimidines Chemical class 0.000 description 1
- 150000005010 aminoquinolines Chemical class 0.000 description 1
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- 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 1
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- AYNUCZFIHUUAIZ-UHFFFAOYSA-N s-(2h-triazol-4-yl)thiohydroxylamine Chemical compound NSC1=CNN=N1 AYNUCZFIHUUAIZ-UHFFFAOYSA-N 0.000 description 1
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- 238000003786 synthesis reaction Methods 0.000 description 1
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- 229940095064 tartrate Drugs 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-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
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- NGSWKAQJJWESNS-ZZXKWVIFSA-N trans-4-coumaric acid Chemical compound OC(=O)\C=C\C1=CC=C(O)C=C1 NGSWKAQJJWESNS-ZZXKWVIFSA-N 0.000 description 1
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Classifications
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- 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
- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
- C10M133/38—Heterocyclic nitrogen compounds
- C10M133/44—Five-membered ring containing nitrogen and carbon only
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
- C10M133/16—Amides; Imides
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- 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
- C10M2207/02—Hydroxy compounds
- C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
- C10M2207/028—Overbased salts thereof
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- C10M2207/10—Carboxylix acids; Neutral salts thereof
- C10M2207/24—Epoxidised acids; Ester derivatives thereof
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- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/26—Overbased carboxylic acid salts
- C10M2207/262—Overbased carboxylic acid salts derived from hydroxy substituted aromatic acids, e.g. salicylates
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- C10M2207/28—Esters
- C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
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- C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
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- C10M2207/289—Partial esters containing free hydroxy groups
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
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- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
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- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
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- C10M2215/08—Amides
- C10M2215/082—Amides containing hydroxyl groups; Alkoxylated derivatives
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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/086—Imides
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- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/223—Five-membered rings containing nitrogen and carbon only
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- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/22—Heterocyclic nitrogen compounds
- C10M2215/223—Five-membered rings containing nitrogen and carbon only
- C10M2215/224—Imidazoles
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- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/04—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
- C10M2219/046—Overbased sulfonic acid salts
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- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/06—Thio-acids; Thiocyanates; Derivatives thereof
- C10M2219/062—Thio-acids; Thiocyanates; Derivatives thereof having carbon-to-sulfur double bonds
- C10M2219/066—Thiocarbamic type compounds
- C10M2219/068—Thiocarbamate metal salts
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- C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
- C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
- C10M2219/089—Overbased salts
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- 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
- C10M2223/043—Ammonium or amine salts thereof
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- 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
- C10M2223/045—Metal containing thio derivatives
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Description
N−置換マルイミド
本明細書で使用される「アルカ(エン)イル」という用語は、アルキルおよびアルケニル基の両方を含む。
R1は、1から6、1から4、2から3、または3個の炭素原子を典型的には含有するヒドロカルビレンであってもよく;
R2およびR3は、水素、または1から30、もしくは8から20個の炭素原子を含有する直鎖状、分枝状、もしくは環状ヒドロカルビル基などのヒドロカルビル基であってもよく(典型的には、ヒドロカルビル基は直鎖状であっても分枝状であってもよい);
但し、N−置換マルイミドが、炭素原子8個未満のヒドロカルビル基を有する分子を含む場合、N−置換マルイミドはN−置換マルイミドの混合物の形をとり、前記混合物中のヒドロカルビル基は平均総数で少なくとも6、または少なくとも7、または少なくとも10個の炭素原子を有することを条件とし、
但し、R2およびR3は、同時に共に水素ではないことを条件とする)によって表すことができる。
潤滑組成物は、潤滑粘度の油を含む。そのような油には、天然および合成油、水素化分解、水素化、および水素化仕上げから得られた油、精製されていない、精製された、再精製された油、またはこれらの混合物が含まれる。精製されていない、精製された、および再精製された油に関するより詳細な記述は、国際公開第WO2008/147704号、段落[0054]から[0056]に示されている。天然および合成潤滑油に関するより詳細な記述は、WO2008/147704の段落[0058]から[0059]にそれぞれ記載されている。合成油は、Fischer−Tropsch反応により生成してもよく、典型的には水素異性化Fischer−Tropsch炭化水素またはワックスであってもよい。一実施形態では、油は、その他のガスツーリキッド(gas−to−liquid)油と同様にFischer−Tropschガスツーリキッド合成手順により調製され得る。
組成物は、その他の性能の添加剤を任意選択で含む。その他の性能の添加剤は、金属活性低下剤、粘度調整剤、洗浄剤、摩擦調整剤(本発明のN−置換マルイミドの他に)、耐摩耗剤、腐食阻害剤、分散剤、分散剤粘度調整剤、極圧添加剤、酸化防止剤、消泡剤、解乳化剤、流動点降下剤、シール膨張剤、およびそれらの混合物の少なくとも1種を含む。典型的には、完全調合型潤滑油は、これらの性能の添加剤の1種または複数を含有することになる。
本発明の分散剤は、スクシンイミド分散剤またはその混合物であってもよい。一実施形態では、分散剤は、単一の分散剤として存在してもよい。一実施形態では、分散剤は、2種または3種の異なる分散剤の混合物であって、その少なくとも1種がスクシンイミド分散剤である混合物中に存在してもよい。
潤滑組成物は、内燃機関に利用してもよい。内燃機関は、排ガス再循環システムを有しても有していなくてもよい。内燃機関には、排出制御システムまたはターボチャージャを備えてもよい。排出制御システムの例には、ディーゼル微粒子フィルタ(DPF)、または選択的触媒還元(SCR)を用いるシステムが含まれる。
オレイルマルイミドの調製。リンゴ酸175gおよびキシレン131gを、窒素入口、機械式撹拌子、Dean−Stark装置、Friedrichsコンデンサ、およびサーモウェルを備えた1リットルの4つ口丸底フラスコに添加する。得られた混合物を140℃に加熱し、オレイルアミン349gを、滴下漏斗を介して4時間にわたり1滴ずつ添加する。次いでフラスコを140℃でさらに10時間維持し、その後、水43gを除去する。次いで溶媒を、真空中(2.67Pa、または20mmHg)で、2時間にわたり140℃で除去する。反応は、生成物419gを生成する。
ココ−アルキルマルイミドの調製。ココアミン332gをリンゴ酸216gと反応させること以外、EX1で述べたように使用したプロセスに従う。反応は、生成物449gおよび水52gを生成する。
ドデシルマルイミドの調製。ドデシルアミン298gをリンゴ酸216gと反応させること以外、EX1で述べたように使用したプロセスに従う。反応は、生成物426gおよび水52gを生成する。
N−(N’,N’−ジタローアミノプロピル)マルイミドの調製。リンゴ酸74.5gおよびトルエン250cm3を、窒素入口、機械式撹拌子、Dean−Stark装置、Friedrichsコンデンサ、およびサーモウェルを備えた1リットルの4つ口丸底フラスコに添加する。得られた混合物を110℃に加熱し、Duomeen(商標)2HT(N,N−ジタロープロピレンジアミン)324.3gを、滴下漏斗を介して6時間にわたり1滴ずつ添加する。フラスコの内容物を、さらに2時間、110℃で撹拌する。次いでフラスコを、少なくとも16時間、約115℃に加熱する。次いで溶媒を、真空中(2.67Pa、または20mmHg)で、2時間にわたり110℃で除去する。
N−(N’,N’−ジココアミノプロピル)マルイミドの調製。反応は、N,N−ジタロープロピレンジアミンの代わりにN,N−ジココプロピレンジアミン238.6gを用いたこと以外、EX4と同様である。
EX1からEX5で得られた生成物を0.5重量%含有する、一連のSAE 5W−30機関潤滑剤(EL1からEL5)を調製する。
SAE 5W−30潤滑剤を、PCS Instrumentsから入手可能なプログラミングされた温度での高周波数往復リグ(HFRR)で、境界潤滑摩擦性能に関して評価する。評価用のHFRR条件は、200g負荷、75分耐久、1000μmストローク、20ヘルツ周波数、および40℃で15分の後に1分当たり2℃の速度で160℃まで温度を上昇させる温度プロファイルであった。上方試験片は直径6mmの鋼製ボールであり(ANSI E−52100、Rockwell「C」硬度58〜66、および表面仕上げRa<0.05μm)、下方試験片は平らな鋼製ディスクである(ANSI E−52100、Vickers「HV30」硬度190〜210、および表面仕上げRa<0.02μm)。上方および下方の両方の試験片は、共にPCS Instrumentsから入手可能である(部品番号HFRSSP)。次いで摩擦係数を測定する。摩擦係数は、往復方向に平行に測定された摩擦力を、加えられた負荷で割ることにより計算される。摩擦係数の結果は、CEL1、CEL2、およびEL1からEL3に関して得られ、これらを下記の表に示す。
次いで5W−30機関潤滑剤を、ASTM法D6594−06に定義される鉛腐食試験において、鉛腐食に関して評価する。試験終了時の油中の鉛(Pb)の量を測定し、試験開始時の量と比較する。油中のより低い鉛含量は、鉛腐食が少ないことを示す。全体の結果が、各潤滑剤CEL1、CEL2、およびEL1からEL3に関して得られ、その内容は下記の通りである:
例えば、本発明は、以下の項目を提供する。
(項目1)
潤滑粘度の油およびN−置換マルイミドまたはその混合物を含む、潤滑組成物。
(項目2)
前記N−置換マルイミドが、アルカ(エン)イル基であるN−ヒドロカルビル置換基を有する、項目1に記載の潤滑組成物。
(項目3)
前記アルカ(エン)イル基が、1から30、または8から20個の炭素原子を含有し、但し、前記N−置換マルイミドが炭素原子8個未満のヒドロカルビル基を有する分子を含む場合、前記N−置換マルイミドはN−置換マルイミドの混合物の形をとり、前記混合物中の前記ヒドロカルビル基は平均総数で少なくとも6または少なくとも10個の炭素原子を有することを条件とする、項目2に記載の潤滑組成物。
(項目4)
前記N−置換マルイミドが、式(1):
(式中、Rは、1から30、または8から20個の炭素原子を含有するヒドロカルビル基であってもよい)によって表され、但し、前記N−置換マルイミドが炭素原子8個未満のヒドロカルビル基を有する分子を含む場合、前記N−置換マルイミドはN−置換マルイミドの混合物の形をとり、そして前記混合物中の前記ヒドロカルビル基は平均総数で少なくとも6または少なくとも10個の炭素原子を有する、前記項目1から3のいずれかに記載の潤滑組成物。
(項目5)
前記N−置換マルイミドが、前記潤滑組成物の0.1重量%から5重量%、または0.2重量%から3重量%、または0.2重量%超から3重量%の範囲の量で存在する、前記項目1から4のいずれかに記載の潤滑組成物。
(項目6)
(i)0.5重量%以下の硫黄含量、(ii)0.1重量%以下のリン含量、および(iii)1.5重量%以下の硫酸灰を有することを特徴とする、前記項目1から5のいずれかに記載の潤滑組成物。
(項目7)
耐摩耗剤、分散剤、分散剤粘度調整剤、摩擦調整剤、粘度調整剤、酸化防止剤、過塩基性洗浄剤、またはそれらの混合物の少なくとも1種をさらに含む、前記項目1から6のいずれかに記載の潤滑組成物。
(項目8)
前記摩擦調整剤が、アミンの脂肪酸誘導体、脂肪エステル、脂肪エポキシド、脂肪イミダゾリン、アルキルリン酸のアミン塩、脂肪アルキルタルトレート、脂肪アルキル酒石酸イミド、脂肪アルキル酒石酸アミド、およびそれらの混合物からなる群から選択される、項目7に記載の潤滑組成物。
(項目9)
分散剤粘度調整剤をさらに含む、前記項目1から8のいずれかに記載の潤滑組成物。
(項目10)
リン含有耐摩耗剤をさらに含む、前記項目1から9のいずれかに記載の潤滑組成物。
(項目11)
過塩基性洗浄剤をさらに含む、前記項目1から10のいずれかに記載の潤滑組成物。
(項目12)
前記過塩基性洗浄剤が、フェネート、硫黄含有フェネート、スルホネート、サリキサレート、サリチレート、およびそれらの混合物からなる群から選択される、項目11に記載の潤滑組成物。
(項目13)
モリブデン化合物をさらに含み、典型的には前記モリブデン化合物が、モリブデンジアルキルジチオホスフェート、モリブデンジチオカルバメート、モリブデン化合物のアミン塩、およびそれらの混合物からなる群から選択されていてもよい、前記項目1から12のいずれかに記載の潤滑組成物。
(項目14)
内燃機関を潤滑化する方法であって、前記内燃機関に、前記項目1から13のいずれかに記載の潤滑組成物を供給するステップを含む方法。
(項目15)
前記内燃機関が、前記潤滑組成物で潤滑化される鉄または鋼の構成要素を含む、項目14に記載の方法。
(項目16)
摩擦制御または鉛腐食制御をもたらすための、機関潤滑剤でのN−置換マルイミドの使用。
Claims (17)
- 潤滑粘度の油およびN−置換マルイミドまたはその混合物を含む、潤滑組成物であって、前記N−置換マルイミドが、式(1):
(式中、Rは、1から30個の炭素原子を含有するヒドロカルビル基であってもよい)によって表され、
但し、前記N−置換マルイミドが炭素原子8個未満のヒドロカルビル基を有する分子を含む場合、前記N−置換マルイミドはN−置換マルイミドの混合物の形をとり、そして合物中の前記ヒドロカルビル基は平均総数で少なくとも6個の炭素原子を有し、そしてここで、前記潤滑組成物が、(i)0.5重量%以下の硫黄含量、(ii)0.1重量%以下のリン含量、および(iii)1.5重量%以下の硫酸灰を有することを特徴とする、潤滑組成物。 - Rの前記ヒドロカルビル基が8から20個の炭素原子を含有する、請求項1に記載の潤滑組成物。
- 前記N−置換マルイミドが炭素原子8個未満のヒドロカルビル基を有する分子を含む場合、前記N−置換マルイミドはN−置換マルイミドの混合物の形をとり、前記混合物中の前記ヒドロカルビル基は平均総数で少なくとも10個の炭素原子を有する、請求項1に記載の潤滑組成物。
- 前記N−置換マルイミドが、アルカ(エン)イル基であるN−ヒドロカルビル置換基を有する、前記請求項1から3のいずれか一項に記載の潤滑組成物。
- 前記N−置換マルイミドが、前記潤滑組成物の0.1重量%から5重量%の範囲の量で存在する、前記請求項1から4のいずれかに記載の潤滑組成物。
- 前記N−置換マルイミドが、前記潤滑組成物の0.2重量%から3重量%の範囲の量で存在する、前記請求項1から4のいずれかに記載の潤滑組成物。
- 前記N−置換マルイミドが、前記潤滑組成物の0.2重量%超から3重量%の範囲の量で存在する、前記請求項1から4のいずれかに記載の潤滑組成物。
- 耐摩耗剤、分散剤、分散剤粘度調整剤、摩擦調整剤、粘度調整剤、酸化防止剤、過塩基性洗浄剤、またはそれらの混合物の少なくとも1種をさらに含む、前記請求項1から7のいずれかに記載の潤滑組成物。
- 前記摩擦調整剤が、アミンの脂肪酸誘導体、脂肪エステル、脂肪エポキシド、脂肪イミダゾリン、アルキルリン酸のアミン塩、脂肪アルキルタルトレート、脂肪アルキル酒石酸イミド、脂肪アルキル酒石酸アミド、およびそれらの混合物からなる群から選択される、請求項8に記載の潤滑組成物。
- 分散剤粘度調整剤をさらに含む、前記請求項1から9のいずれかに記載の潤滑組成物。
- リン含有耐摩耗剤をさらに含む、前記請求項1から10のいずれかに記載の潤滑組成物。
- 過塩基性洗浄剤をさらに含む、前記請求項1から11のいずれかに記載の潤滑組成物。
- 前記過塩基性洗浄剤が、フェネート、硫黄含有フェネート、スルホネート、サリキサレート、サリチレート、およびそれらの混合物からなる群から選択される、請求項12に記載の潤滑組成物。
- モリブデン化合物をさらに含み、典型的には前記モリブデン化合物が、モリブデンジアルキルジチオホスフェート、モリブデンジチオカルバメート、モリブデン化合物のアミン塩、およびそれらの混合物からなる群から選択されていてもよい、前記請求項1から13のいずれかに記載の潤滑組成物。
- 内燃機関を潤滑化する方法であって、前記内燃機関に、前記請求項1から14のいずれかに記載の潤滑組成物を供給するステップを含む方法。
- 前記内燃機関が、前記潤滑組成物で潤滑化される鉄または鋼の構成要素を含む、請求項15に記載の方法。
- 摩擦制御または鉛腐食制御をもたらすための、機関潤滑剤でのN−置換マルイミドの使用であって、前記N−置換マルイミドが、式(1):
(式中、Rは、1から30個の炭素原子を含有するヒドロカルビル基であってもよい)によって表され、
但し、前記N−置換マルイミドが炭素原子8個未満のヒドロカルビル基を有する分子を含む場合、前記N−置換マルイミドはN−置換マルイミドの混合物の形をとり、そして前記混合物中の前記ヒドロカルビル基は平均総数で少なくとも6個の炭素原子を有することを条件とし、そしてここで、前記潤滑組成物が、(i)0.5重量%以下の硫黄含量、(ii)0.1重量%以下のリン含量、および(iii)1.5重量%以下の硫酸灰を有することを特徴とする、使用。
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PCT/US2010/033474 WO2010132229A1 (en) | 2009-05-13 | 2010-05-04 | Internal combustion engine lubricant |
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WO2010132318A1 (en) | 2009-05-13 | 2010-11-18 | The Lubrizol Corporation | Imides and bis-amides as friction modifiers in lubricants |
CN102459535B (zh) | 2009-05-13 | 2017-12-01 | 路博润公司 | 含苹果酸衍生物的润滑组合物 |
CN106661492A (zh) * | 2014-05-28 | 2017-05-10 | 路博润公司 | 烷基苯酚清净剂 |
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GB828701A (en) | 1955-04-21 | 1960-02-24 | Monsanto Chemicals | Rust-inhibiting compositions and lubricants containing the same |
US4326972A (en) | 1978-06-14 | 1982-04-27 | The Lubrizol Corporation | Concentrates, lubricant compositions and methods for improving fuel economy of internal combustion engine |
US4237022A (en) | 1979-10-01 | 1980-12-02 | The Lubrizol Corporation | Tartarimides and lubricants and fuels containing the same |
US4741848A (en) * | 1986-03-13 | 1988-05-03 | The Lubrizol Corporation | Boron-containing compositions, and lubricants and fuels containing same |
US4952328A (en) | 1988-05-27 | 1990-08-28 | The Lubrizol Corporation | Lubricating oil compositions |
DE69004079D1 (de) * | 1990-05-14 | 1993-11-25 | Ethyl Petroleum Additives Ltd | Antioxidationszusammensetzungen. |
US5338470A (en) | 1992-12-10 | 1994-08-16 | Mobil Oil Corporation | Alkylated citric acid adducts as antiwear and friction modifying additives |
DE4317651A1 (de) * | 1993-05-27 | 1994-12-01 | Hoechst Ag | Substituierte Bernsteinsäureimide |
US6394059B2 (en) * | 2000-01-26 | 2002-05-28 | International Engine Intellectual Property Company, L.L.C. | Front module housing |
US6437009B1 (en) * | 2001-03-29 | 2002-08-20 | Air Products And Chemicals, Inc. | Low foam n-alkyltartarimide and n-alkylmalimide wetting agents |
US7696136B2 (en) | 2004-03-11 | 2010-04-13 | Crompton Corporation | Lubricant compositions containing hydroxy carboxylic acid and hydroxy polycarboxylic acid esters |
US7635669B2 (en) | 2004-10-04 | 2009-12-22 | Afton Chemical Corportation | Compositions comprising at least one hydroxy-substituted carboxylic acid |
US7651987B2 (en) * | 2004-10-12 | 2010-01-26 | The Lubrizol Corporation | Tartaric acid derivatives as fuel economy improvers and antiwear agents in crankcase oils and preparation thereof |
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EP2152838B1 (en) | 2007-05-24 | 2012-10-17 | The Lubrizol Corporation | Lubricating composition containing ashfree antiwear agent based on tartaric acid derivative and a molybdenum compound |
CN102171319A (zh) | 2008-10-02 | 2011-08-31 | 卢布里佐尔公司 | 基本不溶性添加剂向功能流体的输送 |
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