JP5522806B2 - 潤滑剤中の摩擦調整剤としてのシュウ酸ビスアミドまたはアミド−エステル - Google Patents
潤滑剤中の摩擦調整剤としてのシュウ酸ビスアミドまたはアミド−エステル Download PDFInfo
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- JP5522806B2 JP5522806B2 JP2011551127A JP2011551127A JP5522806B2 JP 5522806 B2 JP5522806 B2 JP 5522806B2 JP 2011551127 A JP2011551127 A JP 2011551127A JP 2011551127 A JP2011551127 A JP 2011551127A JP 5522806 B2 JP5522806 B2 JP 5522806B2
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- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 title claims description 52
- 239000003607 modifier Substances 0.000 title claims description 29
- 239000000314 lubricant Substances 0.000 title claims description 24
- 235000006408 oxalic acid Nutrition 0.000 title claims description 17
- 239000000203 mixture Substances 0.000 claims description 99
- 125000004432 carbon atom Chemical group C* 0.000 claims description 68
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 58
- -1 alkyl oxamate Chemical compound 0.000 claims description 56
- 239000003921 oil Substances 0.000 claims description 42
- 230000005540 biological transmission Effects 0.000 claims description 30
- 150000003839 salts Chemical class 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 239000002270 dispersing agent Substances 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 19
- FTQWRYSLUYAIRQ-UHFFFAOYSA-N n-[(octadecanoylamino)methyl]octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCNC(=O)CCCCCCCCCCCCCCCCC FTQWRYSLUYAIRQ-UHFFFAOYSA-N 0.000 claims description 19
- 239000003795 chemical substances by application Substances 0.000 claims description 16
- 239000003599 detergent Substances 0.000 claims description 16
- 150000002148 esters Chemical class 0.000 claims description 16
- 230000001050 lubricating effect Effects 0.000 claims description 16
- 229910052698 phosphorus Inorganic materials 0.000 claims description 13
- 239000011574 phosphorus Substances 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 150000001408 amides Chemical class 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 239000000654 additive Substances 0.000 claims description 7
- 239000003963 antioxidant agent Substances 0.000 claims description 7
- 125000005265 dialkylamine group Chemical group 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- LOMVENUNSWAXEN-UHFFFAOYSA-N Methyl oxalate Chemical compound COC(=O)C(=O)OC LOMVENUNSWAXEN-UHFFFAOYSA-N 0.000 claims description 6
- 230000000996 additive effect Effects 0.000 claims description 5
- RZMZBHSKPLVQCP-UHFFFAOYSA-N ethyl 2-amino-2-oxoacetate Chemical group CCOC(=O)C(N)=O RZMZBHSKPLVQCP-UHFFFAOYSA-N 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 4
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 3
- 150000003901 oxalic acid esters Chemical class 0.000 claims 2
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 150000001412 amines Chemical class 0.000 description 45
- 235000019198 oils Nutrition 0.000 description 40
- 239000000463 material Substances 0.000 description 31
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 26
- 239000012530 fluid Substances 0.000 description 23
- 229910052751 metal Inorganic materials 0.000 description 17
- 239000002184 metal Substances 0.000 description 17
- 239000000047 product Substances 0.000 description 16
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 15
- 235000014113 dietary fatty acids Nutrition 0.000 description 15
- 229930195729 fatty acid Natural products 0.000 description 15
- 239000000194 fatty acid Substances 0.000 description 15
- 235000011007 phosphoric acid Nutrition 0.000 description 15
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 14
- 239000000126 substance Substances 0.000 description 13
- 238000002360 preparation method Methods 0.000 description 11
- 150000001336 alkenes Chemical class 0.000 description 10
- 238000009472 formulation Methods 0.000 description 10
- 229920000768 polyamine Polymers 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 9
- 239000011575 calcium Substances 0.000 description 9
- 229910052791 calcium Inorganic materials 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 9
- 229920000098 polyolefin Polymers 0.000 description 9
- 125000001424 substituent group Chemical group 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 229920013639 polyalphaolefin Polymers 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 239000004034 viscosity adjusting agent Substances 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
- 229920001577 copolymer Polymers 0.000 description 7
- 150000004665 fatty acids Chemical class 0.000 description 7
- 230000002829 reductive effect Effects 0.000 description 7
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000004215 Carbon black (E152) Substances 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 229930195733 hydrocarbon Natural products 0.000 description 6
- 150000002924 oxiranes Chemical class 0.000 description 6
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 6
- 229910052717 sulfur Inorganic materials 0.000 description 6
- 239000011593 sulfur Substances 0.000 description 6
- 239000003760 tallow Substances 0.000 description 6
- 239000011701 zinc Substances 0.000 description 6
- 229910052725 zinc Inorganic materials 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- 239000007859 condensation product Substances 0.000 description 5
- 239000002783 friction material Substances 0.000 description 5
- 150000002430 hydrocarbons Chemical class 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 5
- 150000003141 primary amines Chemical class 0.000 description 5
- 239000013557 residual solvent Substances 0.000 description 5
- 230000000153 supplemental effect Effects 0.000 description 5
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 4
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 229920001281 polyalkylene Polymers 0.000 description 4
- 229920000193 polymethacrylate Polymers 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- 150000003751 zinc Chemical class 0.000 description 4
- BIGYLAKFCGVRAN-UHFFFAOYSA-N 1,3,4-thiadiazolidine-2,5-dithione Chemical compound S=C1NNC(=S)S1 BIGYLAKFCGVRAN-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical compound OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 150000001555 benzenes Chemical class 0.000 description 3
- 235000010338 boric acid Nutrition 0.000 description 3
- 229910052796 boron Inorganic materials 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 150000007942 carboxylates Chemical class 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- BVXOPEOQUQWRHQ-UHFFFAOYSA-N dibutyl phosphite Chemical compound CCCCOP([O-])OCCCC BVXOPEOQUQWRHQ-UHFFFAOYSA-N 0.000 description 3
- 150000005690 diesters Chemical class 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 229920001519 homopolymer Polymers 0.000 description 3
- 150000003949 imides Chemical class 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000010452 phosphate Substances 0.000 description 3
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 3
- 150000003016 phosphoric acids Chemical class 0.000 description 3
- PDEDQSAFHNADLV-UHFFFAOYSA-M potassium;disodium;dinitrate;nitrite Chemical compound [Na+].[Na+].[K+].[O-]N=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O PDEDQSAFHNADLV-UHFFFAOYSA-M 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 150000003335 secondary amines Chemical group 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 230000003068 static effect Effects 0.000 description 3
- 229960002317 succinimide Drugs 0.000 description 3
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 3
- 230000008961 swelling Effects 0.000 description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 description 2
- HWKILGJHKYLMHJ-UHFFFAOYSA-N 2-(2,3-dimethylphenyl)octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCC(C(O)=O)C1=CC=CC(C)=C1C HWKILGJHKYLMHJ-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
- CMGDVUCDZOBDNL-UHFFFAOYSA-N 4-methyl-2h-benzotriazole Chemical compound CC1=CC=CC2=NNN=C12 CMGDVUCDZOBDNL-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 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
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000004103 aminoalkyl group Chemical class 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 238000010533 azeotropic distillation Methods 0.000 description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
- 239000004327 boric acid Substances 0.000 description 2
- 150000001639 boron compounds Chemical class 0.000 description 2
- 150000001642 boronic acid derivatives Chemical class 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 159000000007 calcium salts Chemical class 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
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- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 230000000994 depressogenic effect Effects 0.000 description 2
- JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical class OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- XXUJMEYKYHETBZ-UHFFFAOYSA-N ethyl 4-nitrophenyl ethylphosphonate Chemical compound CCOP(=O)(CC)OC1=CC=C([N+]([O-])=O)C=C1 XXUJMEYKYHETBZ-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000013020 final formulation Substances 0.000 description 2
- 239000003365 glass fiber Substances 0.000 description 2
- RZRNAYUHWVFMIP-HXUWFJFHSA-N glycerol monolinoleate Natural products CCCCCCCCC=CCCCCCCCC(=O)OC[C@H](O)CO RZRNAYUHWVFMIP-HXUWFJFHSA-N 0.000 description 2
- 150000002314 glycerols Chemical class 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical class [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 2
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 2
- 150000002462 imidazolines Chemical class 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 230000000670 limiting effect Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- LMTSQIZQTFBYRL-UHFFFAOYSA-N n'-octadecylethane-1,2-diamine Chemical compound CCCCCCCCCCCCCCCCCCNCCN LMTSQIZQTFBYRL-UHFFFAOYSA-N 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 239000010742 number 1 fuel oil Substances 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 125000001117 oleyl 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])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000002530 phenolic antioxidant Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 150000003014 phosphoric acid esters Chemical class 0.000 description 2
- 229920001083 polybutene Polymers 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 230000002459 sustained effect Effects 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- 150000005691 triesters Chemical class 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical class NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QGLWBTPVKHMVHM-KTKRTIGZSA-N (z)-octadec-9-en-1-amine Chemical compound CCCCCCCC\C=C/CCCCCCCCN QGLWBTPVKHMVHM-KTKRTIGZSA-N 0.000 description 1
- 0 *N(*)CCCNC(C(OO*)=O)=O Chemical compound *N(*)CCCNC(C(OO*)=O)=O 0.000 description 1
- ACFCVXXZCDHCRO-UHFFFAOYSA-N 1-(2-heptadec-1-enyl-4,5-dihydroimidazol-1-yl)ethanol Chemical compound CCCCCCCCCCCCCCCC=CC1=NCCN1C(C)O ACFCVXXZCDHCRO-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
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
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- TYPDOONVJVBDKE-UHFFFAOYSA-N n'-ethyloxamide Chemical compound CCNC(=O)C(N)=O TYPDOONVJVBDKE-UHFFFAOYSA-N 0.000 description 1
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- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
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- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
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- 239000005077 polysulfide Substances 0.000 description 1
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- 239000011591 potassium Substances 0.000 description 1
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- 238000001556 precipitation Methods 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
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- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
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- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 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 1
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical class O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-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
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- 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
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M169/00—Lubricating compositions characterised by containing as components a mixture of at least two types of ingredient selected from base-materials, thickeners or additives, covered by the preceding groups, each of these compounds being essential
- C10M169/04—Mixtures of base-materials and additives
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/085—Phosphorus oxides, acids or salts
-
- 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
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
- C10M2203/1006—Petroleum or coal fractions, e.g. tars, solvents, bitumen used as base material
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- 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
- C10M2215/042—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives thereof
-
- 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
- C10M2215/064—Di- and triaryl amines
-
- 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
- C10M2215/064—Di- and triaryl amines
- C10M2215/065—Phenyl-Naphthyl amines
-
- 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/08—Amides
-
- 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/12—Partial amides of polycarboxylic acids
-
- 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/28—Amides; Imides
-
- 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
- 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—Overbasedsulfonic acid salts
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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
- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
- C10M2219/06—Thio-acids; Thiocyanates; Derivatives thereof
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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
- 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
- C10M2223/049—Phosphite
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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
- C10M2227/00—Organic non-macromolecular compounds containing atoms of elements not provided for in groups C10M2203/00, C10M2207/00, C10M2211/00, C10M2215/00, C10M2219/00 or C10M2223/00 as ingredients in lubricant compositions
- C10M2227/06—Organic compounds derived from inorganic acids or metal salts
- C10M2227/061—Esters derived from boron
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
Description
(項目1)
潤滑粘性のオイル;および
少なくとも2つの約12〜約22個の炭素原子のヒドロカルビル基を含むN−置換シュウ酸ビスアミドまたはアミド−エステル
を含む組成物。
(項目2)
前記N−置換シュウ酸ビスアミドまたはアミドエステルが、式:
(式中、R 1 、R 2 、R 3 およびR 4 の少なくとも2つは独立に、約12〜約22個の炭素原子のヒドロカルビル基を含む基であり、前記基R 1 、R 2 、R 3 およびR 4 の最大で2つは独立に、水素または10個以下の炭素原子のヒドロカルビル基である)
で表されるビスアミドを含む、項目1に記載の組成物。
(項目3)
R 3 およびR 4 が水素である、項目2に記載の組成物。
(項目4)
R 1 およびR 4 が水素である、項目2に記載の組成物。
(項目5)
前記基R 1 、R 2 、R 3 およびR 4 の2つが独立に、約12〜約22個の炭素原子のアルキル基である、項目2から4のいずれかに記載の組成物。
(項目6)
前記基R 1 、R 2 、R 3 およびR 4 の2つが独立に、N−ヒドロカルビル−置換アミノアルキル基であり、該ヒドロカルビル置換基が約12〜約22個の炭素原子を含み、該アルキル部分が1〜4個の炭素原子を含む、項目2から4のいずれかに記載の組成物。
(項目7)
前記N−置換シュウ酸ビスアミドまたはアミドエステルが、式
(式中、それぞれのR 1 およびR 2 は独立に、約12〜約18個の炭素原子のアルキル基である)
で表されるビスアミドを含む、項目1、2、3または5のいずれかに記載の組成物。
(項目8)
前記N−置換シュウ酸ビスアミドまたはアミド−エステルが、式:
(式中、R 1 およびR 2 は独立に、約12〜約22個の炭素原子のヒドロカルビル基であり、R 10 は1〜約22個の炭素原子のヒドロカルビル基である)
で表されるアミド−エステルを含む、項目1に記載の組成物。
(項目9)
潤滑粘性のオイル、およびジアルキルアミンとオキサミン酸アルキルを反応させるプロセスによって得られるか、または得ることができる生成物を含む組成物。
(項目10)
前記ジアルキルアミンがジココアミンであり、前記オキサミン酸アルキルがオキサミン酸エチルである、項目9に記載の組成物。
(項目11)
前記N−置換シュウ酸ビスアミドまたはアミド−エステルが、式
(式中、R 5 およびR 7 は独立に、約12〜約22個の炭素原子のヒドロカルビル基であり、R 6 およびR 8 は独立に、水素あるいは10個以下の炭素原子のヒドロカルビル基または約12〜約22個の炭素原子のヒドロカルビル基である)
で表されるビスアミドを含む、項目1、2、4または6のいずれかに記載の組成物。
(項目12)
前記N−置換シュウ酸ビスアミドまたはアミド−エステルが、式:
(式中、R 5 およびR 6 は独立に、約12〜約22個の炭素原子のヒドロカルビル基であり、R 10 は1〜約22個の炭素原子のヒドロカルビル基である)
で表されるアミド−エステルを含む、項目1に記載の組成物。
(項目13)
N,N−ジタロープロピレンジアミンをシュウ酸ジメチルと反応させるプロセスによって得られるか、または得ることができる生成物を含む、自動変速機のための摩擦調整剤として使用するのに適した組成物。
(項目14)
前記N−置換シュウ酸ビスアミドまたはアミド−エステルの量が約0.1〜約10重量%である、項目1から13のいずれかに記載の組成物。
(項目15)
分散剤、洗剤、酸化防止剤、シール膨張剤および摩耗防止剤からなる群から選択される少なくとも1つのさらなる添加剤をさらに含む、項目1から14のいずれかに記載の組成物。
(項目16)
有機ホウ酸エステル、有機ホウ酸塩、有機リンの酸のエステル(phosphorus ester)、有機リンの酸の塩(phosphorus salt)、無機リンの酸および無機リンの酸の塩からなる群から選択される少なくとも1つの添加剤をさらに含む、項目1から15のいずれかに記載の組成物。
(項目17)
項目1から16のいずれかに記載の潤滑剤を変速機に供給することを含む変速機を潤滑化させる方法。
本開示技術は、変速機用の摩擦調整剤として使用するのに適した組成物であって、潤滑粘性のオイル、および12〜22個の炭素原子の少なくとも2つのヒドロカルビル基を含むN−置換シュウ酸ビスアミドまたはアミド−エステルを含む組成物を提供する。特定の実施形態では、そのビスアミドまたはアミド−エステルは第1級アミノ基を含まない。
脂肪ホスファイト ホウ酸化アルコキシ化脂肪アミン
脂肪酸アミド 脂肪酸の金属塩
脂肪エポキシド 硫化オレフィン
ホウ酸化脂肪エポキシド 脂肪イミダゾリン
上記で論じた脂肪アミン以外の脂肪アミン
カルボン酸とポリアルキレン−ポリアミンの
縮合生成物
グリセロールエステル アルキルサリシレートの金属塩
ホウ酸化グリセロールエステル アルキルリン酸のアミン塩
アルコキシ化脂肪アミン エトキシ化アルコール
オキサゾリン イミダゾリン
ヒドロキシアルキルアミド ポリヒドロキシ第3級アミン
およびその2つ以上の混合物
が含まれ得る。
炭化水素置換基。すなわち、脂肪族(例えば、アルキルまたはアルケニル)、脂環式(例えば、シクロアルキル、シクロアルケニル)置換基および芳香族−、脂肪族−および脂環式−置換芳香族置換基、ならびにその環が分子の他の部分を介して完成している環状置換基(例えば、2つの置換基が一緒に環を形成する);
置換炭化水素置換基。すなわち本発明の関連で、置換基(例えば、ハロ(特にクロロおよびフルオロ)、ヒドロキシ、アルコキシ、メルカプト、アルキルメルカプト、ニトロ、ニトロソおよびスルホキシ)の主に炭化水素的特徴を変えない非炭化水素基を含む置換基;
ヘテロ置換基。すなわち、本発明の関連で主に炭化水素的特徴を有しているが、環または鎖の中に炭素以外のもの(そうでない場合炭素原子からなる)を含み、ピリジル、フリル、チエニルおよびイミダゾリルのような置換基を包含する置換基。ヘテロ原子にはイオウ、酸素および窒素が含まれる。一般に、ヒドロカルビル基中の10個の炭素原子毎にわずか2つまたはわずか1つのヘテロ原子が存在する。一般にヒドロカルビル基中にヘテロ原子は存在しない。
(上記式(I)で表される物質を調製するため)。ジココアミン(150g)とキシレン(550mL)を窒素雰囲気下で撹拌しながら混合する。この混合物に、オキサミン酸エチル(58.6g)を一括して加える。混合物を110℃に加熱し、7時間撹拌し、ディーンスタークトラップ中にエタノールを収集する。次いで混合物を135℃に加熱し、5時間撹拌し、蒸留によりキシレンを除去する。混合物をさらに155℃に加熱し、7時間撹拌し、次いで冷却し、ガラス繊維ろ紙でろ過する。ロータリーエバポレーターを用いて減圧下で残留溶媒をすべて除去してオレンジ色の油状生成物を得る。
(上記式(II)で表される物質を調製するため)。パート1、N−ココイソステアラミド。イソステアリン酸(215g)とキシレン(1L)を窒素雰囲気下で撹拌しながら混合する。Armeen C(商標)(156g)を一括して加え、混合物を148℃で12時間撹拌し、ディーンスタークトラップを用いて共沸蒸留により水(13.4g)を除去する。混合物を冷却し、ロータリーエバポレーターを用いて減圧下で残留溶媒をすべて除去する。
(上記式(III)で表される物質を調製するため)。Duomeen C(商標)(112g)とトルエン(350mL)を窒素雰囲気下で撹拌しながら混合する。シュウ酸ジメチル(24.25g)を一括して加え、撹拌しながら反応物を95℃で5時間加熱し、ディーンスタークトラップを用いて共沸蒸留によりメタノールを除去する。次いで、撹拌しながら混合物を105℃で4時間加熱する。ロータリーエバポレーターを用いて減圧下で残留溶媒をすべて除去する。
(上記式(IV)で表される物質を調製するため)。Duomeen 2HT(商標)(N,N−ジタロープロピレンジアミン、207.8g)とトルエン(400mL)を窒素下で撹拌しながら混合する。この混合物に、シュウ酸ジメチル(20.4g)を一括して加える。混合物を112℃に加熱し、6.5時間撹拌する。撹拌しながら混合物を120℃に7時間さらに加熱し、次いで冷却する。ロータリーエバポレーター(rotary evaporation)を用いて減圧下で残留溶媒をすべて除去する。
3.5%スクシンイミド分散剤(41.5%のオイルを含む)
0.2%亜リン酸ジブチル
0.1%リン酸
0.1%ホウ酸エステル
0.9%アミン酸化防止剤
0.4%シール膨張剤
1.1%スルホン酸カルシウム洗剤(50%のオイルを含む)
0.06%置換チアジアゾール
0.2%流動点降下剤
0.04%エトキシ化アミン
9.6%分散剤粘度調整剤(25%のオイルを含む)
0.04%他の少量成分
残分:鉱油(主に3〜6cSt)
基本配合物B:
3.5%スクシンイミド分散剤(41.5%のオイルを含む)
0.2%亜リン酸ジブチル
0.1%リン酸
0.9%アミン酸化防止剤
0.4%シール膨張剤
0.2%流動点降下剤
9.6%分散剤粘度調整剤(25%のオイルを含む)
0.03%他の少量成分
残分:鉱油(主に3〜6cSt)
試験用の潤滑剤は、以下の表で特定される調製例からの材料の1つを、表示した基本配合物に加えて調製する。得られた潤滑剤を、可変速度摩擦試験であるVSFT試験にかける。VSFT装置は、金属表面に対して回転する金属または他の摩擦材料であってよいディスクからなる。具体的な試験で用いる摩擦材料は、表に示したような自動変速機クラッチで一般に使用される様々な市販の摩擦材料である。試験は、3つの温度と2つの負荷レベルで実施する。VSFTで測定された摩擦係数を、一定圧力でのいくつかの速度掃引(number speed sweep)にわたって滑り速度(50および200r.p.m.)に対してプロットする。結果を最初に、0時間から52時間まで4時間間隔で、40、80および120℃と24kgおよび40kg(235および392N)力で記録して、時間の関数としてのμ−v曲線の勾配で示す。一般に、その勾配は最初、ある程度のばらつきで正となり、徐々に低下して、一定の期間の後おそらく負になってくる。正の勾配の期間がより長いことが望ましい。
b. 参考例
c. 3つの試行の平均
結果は、特にそれらの物質が存在しない基本配合物と比較して、本発明技術の物質による望ましい摩擦性能を示している。結果は、0.25%と比較して0.35もしくは0.5%またはそれ以上、例えば1.0または2.5%の比較的高い濃度で、より良好な性能が得られることもあることも示している。実施例6の比較的低い値であっても、参考例Yのものより良好である(特に80℃で)。
Claims (11)
- 潤滑粘性のオイル、およびジアルキルアミンとオキサミン酸アルキルを反応させるプロセスによって得られるか、または得ることができる生成物を含む組成物。
- 前記ジアルキルアミンがジココアミンであり、前記オキサミン酸アルキルがオキサミン酸エチルである、請求項4に記載の組成物。
- N,N−ジタロープロピレンジアミンをシュウ酸ジメチルと反応させるプロセスによって得られるか、または得ることができる生成物を含む、自動変速機のための摩擦調整剤として使用するのに適した組成物。
- 分散剤、洗剤、酸化防止剤、シール膨張剤および摩耗防止剤からなる群から選択される少なくとも1つのさらなる添加剤をさらに含む、請求項1から8のいずれかに記載の組成物。
- 有機ホウ酸エステル、有機ホウ酸塩、有機リンの酸のエステル(phosphorus
ester)、有機リンの酸の塩(phosphorus salt)、無機リンの酸および無機リンの酸の塩からなる群から選択される少なくとも1つの添加剤をさらに含む、請求項1から9のいずれかに記載の組成物。 - 請求項1から10のいずれかに記載の潤滑剤を変速機に供給することを含む変速機を潤滑化させる方法。
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PCT/US2010/023855 WO2010096321A1 (en) | 2009-02-18 | 2010-02-11 | Oxalic acid bis-amides or amide-ester as friction modifiers in lubricants |
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US8883699B2 (en) * | 2011-10-25 | 2014-11-11 | Dongwoo Fine-Chem Co., Ltd. | Resist stripping composition and method of stripping resist using the same |
KR102425108B1 (ko) * | 2014-06-27 | 2022-07-26 | 더루우브리졸코오포레이션 | 변속기 유체에 양호한 마찰 성능을 제공하는 마찰조정제 혼합물 |
EP3218454B1 (en) * | 2014-11-12 | 2022-01-12 | The Lubrizol Corporation | Mixed phosphorus esters for lubricant applications |
JP6789615B2 (ja) * | 2015-03-31 | 2020-11-25 | 出光興産株式会社 | 変速機用潤滑油組成物 |
WO2016164345A1 (en) | 2015-04-09 | 2016-10-13 | The Lubrizol Corporation | Lubricants containing quaternary ammonium compounds |
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-
2010
- 2010-02-11 EP EP10703604.8A patent/EP2398876B1/en active Active
- 2010-02-11 US US13/201,671 patent/US8691740B2/en active Active
- 2010-02-11 WO PCT/US2010/023855 patent/WO2010096321A1/en active Application Filing
- 2010-02-11 KR KR1020117021533A patent/KR101720812B1/ko active IP Right Grant
- 2010-02-11 CN CN201080016878.4A patent/CN102395663B/zh active Active
- 2010-02-11 JP JP2011551127A patent/JP5522806B2/ja active Active
- 2010-02-11 BR BRPI1008704A patent/BRPI1008704B1/pt not_active IP Right Cessation
- 2010-02-11 CN CN201410479879.2A patent/CN104388147B/zh active Active
- 2010-02-11 CA CA2752964A patent/CA2752964C/en not_active Expired - Fee Related
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Also Published As
Publication number | Publication date |
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US8691740B2 (en) | 2014-04-08 |
CN102395663B (zh) | 2014-10-29 |
BRPI1008704A2 (pt) | 2016-03-08 |
US20120021958A1 (en) | 2012-01-26 |
KR101720812B1 (ko) | 2017-03-28 |
KR20110135394A (ko) | 2011-12-16 |
EP2398876B1 (en) | 2014-11-19 |
CN104388147B (zh) | 2018-01-09 |
CA2752964A1 (en) | 2010-08-26 |
CN104388147A (zh) | 2015-03-04 |
EP2398876A1 (en) | 2011-12-28 |
CN102395663A (zh) | 2012-03-28 |
CA2752964C (en) | 2017-01-17 |
JP2012518071A (ja) | 2012-08-09 |
WO2010096321A1 (en) | 2010-08-26 |
BRPI1008704B1 (pt) | 2018-05-08 |
JP2014101528A (ja) | 2014-06-05 |
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