EP1674557B1 - Composition d'additif anti-vibratoire et composition d'huile lubrifiante la contenante - Google Patents
Composition d'additif anti-vibratoire et composition d'huile lubrifiante la contenante Download PDFInfo
- Publication number
- EP1674557B1 EP1674557B1 EP05257367.2A EP05257367A EP1674557B1 EP 1674557 B1 EP1674557 B1 EP 1674557B1 EP 05257367 A EP05257367 A EP 05257367A EP 1674557 B1 EP1674557 B1 EP 1674557B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- lubricating oil
- oil composition
- shudder
- monosuccinimide
- substituted succinic
- 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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- 239000000203 mixture Substances 0.000 title claims description 170
- 239000000654 additive Substances 0.000 title claims description 85
- 239000010687 lubricating oil Substances 0.000 title claims description 78
- 230000000996 additive effect Effects 0.000 title claims description 76
- -1 phosphite compound Chemical class 0.000 claims description 97
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 77
- 239000002270 dispersing agent Substances 0.000 claims description 66
- 150000002148 esters Chemical class 0.000 claims description 46
- 230000005540 biological transmission Effects 0.000 claims description 41
- 125000004432 carbon atom Chemical group C* 0.000 claims description 33
- 239000003921 oil Substances 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 22
- 229920005862 polyol Polymers 0.000 claims description 22
- 150000003077 polyols Chemical class 0.000 claims description 22
- 239000012530 fluid Substances 0.000 claims description 21
- 230000007935 neutral effect Effects 0.000 claims description 21
- 150000001412 amines Chemical class 0.000 claims description 20
- IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical group CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 claims description 16
- 230000001050 lubricating effect Effects 0.000 claims description 15
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 14
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 150000003140 primary amides Chemical class 0.000 claims description 6
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims 5
- 229920000768 polyamine Polymers 0.000 description 55
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical class O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 31
- 125000003342 alkenyl group Chemical group 0.000 description 28
- 125000000217 alkyl group Chemical group 0.000 description 28
- 239000003112 inhibitor Substances 0.000 description 28
- 239000002199 base oil Substances 0.000 description 25
- 229940014800 succinic anhydride Drugs 0.000 description 25
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical class ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 23
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 20
- 230000003647 oxidation Effects 0.000 description 20
- 238000007254 oxidation reaction Methods 0.000 description 20
- 229960002317 succinimide Drugs 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 16
- GEPDYQSQVLXLEU-AATRIKPKSA-N methyl (e)-3-dimethoxyphosphoryloxybut-2-enoate Chemical compound COC(=O)\C=C(/C)OP(=O)(OC)OC GEPDYQSQVLXLEU-AATRIKPKSA-N 0.000 description 13
- 239000003607 modifier Substances 0.000 description 13
- 238000012360 testing method Methods 0.000 description 12
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 11
- SPBMDAHKYSRJFO-UHFFFAOYSA-N didodecyl hydrogen phosphite Chemical compound CCCCCCCCCCCCOP(O)OCCCCCCCCCCCC SPBMDAHKYSRJFO-UHFFFAOYSA-N 0.000 description 11
- 229910052751 metal Inorganic materials 0.000 description 11
- 239000002184 metal Substances 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 10
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 10
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- 229910052791 calcium Inorganic materials 0.000 description 9
- 239000011575 calcium Substances 0.000 description 9
- 229920001577 copolymer Polymers 0.000 description 9
- 239000006260 foam Substances 0.000 description 9
- 229930195733 hydrocarbon Natural products 0.000 description 9
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 9
- 230000008569 process Effects 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 150000004867 thiadiazoles Chemical class 0.000 description 9
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 8
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 8
- 125000002947 alkylene group Chemical group 0.000 description 8
- 150000002430 hydrocarbons Chemical class 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 229920000098 polyolefin Polymers 0.000 description 8
- 229910052710 silicon Inorganic materials 0.000 description 8
- 239000010703 silicon Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 8
- OIQXFRANQVWXJF-LIQNAMIISA-N (1s,2z,4r)-2-benzylidene-4,7,7-trimethylbicyclo[2.2.1]heptan-3-one Chemical compound O=C([C@]1(C)CC[C@H]2C1(C)C)\C2=C/C1=CC=CC=C1 OIQXFRANQVWXJF-LIQNAMIISA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- 239000004215 Carbon black (E152) Substances 0.000 description 7
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 150000005846 sugar alcohols Polymers 0.000 description 7
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical class OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 6
- 239000004711 α-olefin Substances 0.000 description 6
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 5
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 5
- 239000004952 Polyamide Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 239000003599 detergent Substances 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 125000000623 heterocyclic group Chemical group 0.000 description 5
- 229920002647 polyamide Polymers 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-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
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 4
- 239000004327 boric acid Substances 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 230000007246 mechanism Effects 0.000 description 4
- 239000002480 mineral oil Substances 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- 235000021317 phosphate Nutrition 0.000 description 4
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 4
- 229920001281 polyalkylene Polymers 0.000 description 4
- 229920001083 polybutene Polymers 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 235000011044 succinic acid Nutrition 0.000 description 4
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 4
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 3
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 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 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 150000008064 anhydrides Chemical group 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 235000006708 antioxidants Nutrition 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 150000001639 boron compounds Chemical class 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 150000002431 hydrogen Chemical group 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- LSHROXHEILXKHM-UHFFFAOYSA-N n'-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCN LSHROXHEILXKHM-UHFFFAOYSA-N 0.000 description 3
- 150000004885 piperazines Chemical class 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 150000003139 primary aliphatic amines Chemical class 0.000 description 3
- 150000003141 primary amines Chemical class 0.000 description 3
- 150000003335 secondary amines Chemical class 0.000 description 3
- 239000000600 sorbitol Substances 0.000 description 3
- 239000001384 succinic acid Substances 0.000 description 3
- 229960001124 trientine Drugs 0.000 description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- 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 2
- SZAQZZKNQILGPU-UHFFFAOYSA-N 2-[1-(2-hydroxy-3,5-dimethylphenyl)-2-methylpropyl]-4,6-dimethylphenol Chemical compound C=1C(C)=CC(C)=C(O)C=1C(C(C)C)C1=CC(C)=CC(C)=C1O SZAQZZKNQILGPU-UHFFFAOYSA-N 0.000 description 2
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
- 229930195725 Mannitol Natural products 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 229920002367 Polyisobutene Polymers 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 230000002152 alkylating effect Effects 0.000 description 2
- 125000005263 alkylenediamine group Chemical group 0.000 description 2
- 150000001409 amidines Chemical class 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 description 2
- PFURGBBHAOXLIO-UHFFFAOYSA-N cyclohexane-1,2-diol Chemical compound OC1CCCCC1O PFURGBBHAOXLIO-UHFFFAOYSA-N 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000012990 dithiocarbamate Substances 0.000 description 2
- UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical compound NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- 150000003949 imides Chemical class 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
- GKQPCPXONLDCMU-CCEZHUSRSA-N lacidipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC=CC=C1\C=C\C(=O)OC(C)(C)C GKQPCPXONLDCMU-CCEZHUSRSA-N 0.000 description 2
- 238000005461 lubrication Methods 0.000 description 2
- 239000000594 mannitol Substances 0.000 description 2
- 235000010355 mannitol Nutrition 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229910052750 molybdenum Inorganic materials 0.000 description 2
- 239000011733 molybdenum Substances 0.000 description 2
- 150000002763 monocarboxylic acids Chemical class 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 2
- 229920013639 polyalphaolefin Polymers 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- GGQQNYXPYWCUHG-RMTFUQJTSA-N (3e,6e)-deca-3,6-diene Chemical compound CCC\C=C\C\C=C\CC GGQQNYXPYWCUHG-RMTFUQJTSA-N 0.000 description 1
- PRBHEGAFLDMLAL-GQCTYLIASA-N (4e)-hexa-1,4-diene Chemical compound C\C=C\CC=C PRBHEGAFLDMLAL-GQCTYLIASA-N 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- FFJCNSLCJOQHKM-CLFAGFIQSA-N (z)-1-[(z)-octadec-9-enoxy]octadec-9-ene Chemical compound CCCCCCCC\C=C/CCCCCCCCOCCCCCCCC\C=C/CCCCCCCC FFJCNSLCJOQHKM-CLFAGFIQSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical group ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- WJECKFZULSWXPN-UHFFFAOYSA-N 1,2-didodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1CCCCCCCCCCCC WJECKFZULSWXPN-UHFFFAOYSA-N 0.000 description 1
- YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical class C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 description 1
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 1
- GGPQIDNOBBRMCI-UHFFFAOYSA-N 1,4-di(piperazin-1-yl)piperazine Chemical compound C1CNCCN1N1CCN(N2CCNCC2)CC1 GGPQIDNOBBRMCI-UHFFFAOYSA-N 0.000 description 1
- XDHVNMPVLPEHND-UHFFFAOYSA-N 1-(2-piperazin-1-ylethyl)piperazine Chemical compound C1CNCCN1CCN1CCNCC1 XDHVNMPVLPEHND-UHFFFAOYSA-N 0.000 description 1
- WJVAPEMLIPHCJB-UHFFFAOYSA-N 1-n-methylpropane-1,2-diamine Chemical compound CNCC(C)N WJVAPEMLIPHCJB-UHFFFAOYSA-N 0.000 description 1
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 1
- 125000004825 2,2-dimethylpropylene group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[*:1])C([H])([H])[*:2] 0.000 description 1
- OPLCSTZDXXUYDU-UHFFFAOYSA-N 2,4-dimethyl-6-tert-butylphenol Chemical compound CC1=CC(C)=C(O)C(C(C)(C)C)=C1 OPLCSTZDXXUYDU-UHFFFAOYSA-N 0.000 description 1
- GSOYMOAPJZYXTB-UHFFFAOYSA-N 2,6-ditert-butyl-4-(3,5-ditert-butyl-4-hydroxyphenyl)phenol Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(C=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 GSOYMOAPJZYXTB-UHFFFAOYSA-N 0.000 description 1
- QHPKIUDQDCWRKO-UHFFFAOYSA-N 2,6-ditert-butyl-4-[2-(3,5-ditert-butyl-4-hydroxyphenyl)propan-2-yl]phenol Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(C(C)(C)C=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 QHPKIUDQDCWRKO-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
- XQESJWNDTICJHW-UHFFFAOYSA-N 2-[(2-hydroxy-5-methyl-3-nonylphenyl)methyl]-4-methyl-6-nonylphenol Chemical compound CCCCCCCCCC1=CC(C)=CC(CC=2C(=C(CCCCCCCCC)C=C(C)C=2)O)=C1O XQESJWNDTICJHW-UHFFFAOYSA-N 0.000 description 1
- HVOBSBRYQIYZNY-UHFFFAOYSA-N 2-[2-(2-aminoethylamino)ethylamino]ethanol Chemical compound NCCNCCNCCO HVOBSBRYQIYZNY-UHFFFAOYSA-N 0.000 description 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- CYOIAXUAIXVWMU-UHFFFAOYSA-N 2-[2-aminoethyl(2-hydroxyethyl)amino]ethanol Chemical compound NCCN(CCO)CCO CYOIAXUAIXVWMU-UHFFFAOYSA-N 0.000 description 1
- PAOXFRSJRCGJLV-UHFFFAOYSA-N 2-[4-(2-aminoethyl)piperazin-1-yl]ethanamine Chemical compound NCCN1CCN(CCN)CC1 PAOXFRSJRCGJLV-UHFFFAOYSA-N 0.000 description 1
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 1
- PTJWCLYPVFJWMP-UHFFFAOYSA-N 2-[[3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)COCC(CO)(CO)CO PTJWCLYPVFJWMP-UHFFFAOYSA-N 0.000 description 1
- GTLMTHAWEBRMGI-UHFFFAOYSA-N 2-cyclohexyl-4-methylphenol Chemical compound CC1=CC=C(O)C(C2CCCCC2)=C1 GTLMTHAWEBRMGI-UHFFFAOYSA-N 0.000 description 1
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- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
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- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
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- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
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- 238000003860 storage Methods 0.000 description 1
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- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
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- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
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- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
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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
- C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
- C10M141/10—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic phosphorus-containing compound
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic 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
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/283—Esters of polyhydroxy compounds
-
- 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
- C10N2040/042—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for automatic transmissions
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/04—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
- C10N2040/045—Oil-bath; Gear-boxes; Automatic transmissions; Traction drives for continuous variable transmission [CVT]
Definitions
- alkylating hydrocarbons may likewise be used with maleic anhydride to produce alkenyl succinic anhydride.
- suitable alkylating hydrocarbons include cyclic, linear, branched and internal or alpha olefins with molecular weights in the range 100-4,500 or more with molecular weights in the range of 200-2,000 being more preferred.
- alpha olefins obtained from the thermal cracking of paraffin wax. Generally, these olefins range from 5-20 carbon atoms in length.
- Another source of alpha olefins is the ethylene growth process which gives even number carbon olefins.
- the more preferred polyamine is a polyalkylene polyamine, including alkylene diamine, and including substituted polyamines, e.g., alkyl substituted polyalkylene polyamine.
- the alkylene group contains from 2 to 6 carbon atoms, there being preferably from 2 to 3 carbon atoms between the nitrogen atoms.
- groups are exemplified by ethylene, 1,2-propylene, 2,2-dimethylpropylene, trimethylene, etc.
- Examples of such polyamines include ethylene diamine, diethylene triamine, di(trimethylene)triamine, dipropylene triamine, triethylene tetramine, tripropylene tetramine, tetraethylene pentamine, and pentaethylene hexamine.
- Typical polyamines that can be used to form the compounds described herein include the following: ethylene diamine, 1,2-propylene diamine, 1,3-propylene diamine, diethylene triamine, triethylene tetramine, hexamethylene diamine, tetraethylene pentamine, methylaminopropylene diamine, N-(betaaminoethyl)piperazine, N,N'-di(betaaminoethyl)piperazine, N,N'-di(beta-aminoethyl)-imidazolidone-2, N-(beta-cyanoethyl)ethane-1,2-diamine, 1,3,6,9-tetraaminooctadecane, 1,3,6-triamino-9-oxadecane, N-(beta-aminoethyl)diethanolamine, N-methyl-1,2-propanediamine, 2-(2-aminoethylamin
- a is an integer from 1 to 6.
- Hydrocarbon synthetic oils may include, for example, oils prepared from the polymerization of ethylene, polyalphaolefin or PAO oils, or oils prepared from hydrocarbon synthesis procedures using carbon monoxide and hydrogen gases such as in a Fisher-Tropsch process.
- Useful synthetic hydrocarbon oils include liquid polymers of alpha olefins having the proper viscosity. Especially useful are the hydrogenated liquid oligomers of C 6 to C 12 olefins such as 1-decene trimer.
- alkyl benzenes of proper viscosity such as didodecyl benzene, can be used.
- Disalicylidene propylenediamine triazole derivatives, thiadiazole derivatives, and mercaptobenzimidazoles.
- the anti-shudder additive composition is prepared by mixing the following two components at elevated temperatures of about 70°F to 195°F, for example, at about 140°F: (a) at least one neutral phosphite compound, such as trihydrocarbyl phosphite, such as trialkyl phosphite, such as trilauryl phosphite; and (b) at least one phosphorous-free hydrocarbyl substituted succinic dispersant selected from the group consisting of a hydrocarbyl bissuccinimide and a hydrocarbyl substituted succinic ester of a polyol and mixtures thereof, wherein the hydrocarbyl substituent has at least 50 carbon atoms.
- a neutral phosphite compound such as trihydrocarbyl phosphite, such as trialkyl phosphite, such as trilauryl phosphite
- at least one phosphorous-free hydrocarbyl substituted succinic dispersant selected
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
Claims (18)
- Composition d'additif anti-vibratoire comprenant :(a) au moins un composé neutre de phosphite, le composé neutre de phosphite étant un trihydrocarbylephosphite ; et(b) au moins un dispersant succinique substitué d'hydrocarbyle sélectionné parmi le groupe constitué en un ester succinique d'un polyole, substitué d'hydrocarbyle, et d'un mélange d'un ester succinique d'un polyole, substitué d'hydrocarbyle, avec un bissuccinimide d'hydrocarbyle, le substituant d'hydrocarbyle ayant au moins 50 atomes de carbone,
où la composition d'additif ne comprend pas d'amine éthoxylée, et où la composition d'additif ne comprend pas d'amide primaire d'un acide carboxylique à longue chaine. - Composition d'additif anti-vibratoire selon la revendication 1, dans laquelle le trihydrocarbylephosphite est un trialkylephosphite.
- Composition d'additif anti-vibratoire selon la revendication 2, dans laquelle le trialkylephosphite est le trilaurylephosphite.
- Composition d'additif anti-vibratoire selon la revendication 1, dans laquelle le bissuccinimide d'hydrocarbyle est un bissuccinimide d'hydrocarbyle boré.
- Composition d'additif anti-vibratoire selon la revendication 1, dans laquelle l'ester succinique d'un polyole, substitué d'hydrocarbyle, est un ester du pentaérythritole.
- Composition d'huile lubrifiante, comprenant :(a) supérieur à 50 pour cent en poids d'une huile à viscosité lubrifiante, sur la base du poids total de la composition d'huile lubrifiante ; et(b) de 0,11 pour cent en poids à 11,0 pour cent en poids d'une composition d'additif anti-vibratoire selon une quelconque des revendications 1 à 5, sur la base du poids total de la composition d'huile lubrifiante, et sous réserve que, si la composition d'huile lubrifiante comprend en plus un monosuccinimide, alors le rapport en poids entre le dispersant succinique substitué d'hydrocarbyle et monosuccinimide est au moins 7:3.
- Utilisation d'une composition d'huile lubrifiante selon la revendication 6 comme fluide de transmission, éventuellement comme fluide de transmission automatique.
- Utilisation selon la revendication 7, dans laquelle le fluide de transmission est un fluide de transmission à variation continue.
- Composition d'huile lubrifiante selon la revendication 6, dans laquelle la composition d'huile lubrifiante contient en plus un monosuccinimide et le rapport en poids entre le dispersant succinique substitué d'hydrocarbyle et monosuccinimide est au moins 7,5:2,5.
- Composition d'huile lubrifiante selon la revendication 9, dans laquelle et le rapport en poids entre le dispersant succinique substitué d'hydrocarbyle et mono-succinimide est au moins 8:2.
- Composition d'huile lubrifiante selon la revendication 10, dans laquelle et le rapport en poids entre le dispersant succinique substitué d'hydrocarbyle et monosuccinimide est au moins 9:1.
- Procédé de préparation d'une composition d'additif anti-vibratoire comprenant : le mélange d'entre 0,1 pour cent en poids et 90,9 pour cent en poids d'au moins un composé neutre de phosphite, le composé neutre de phosphite étant un trihydrocarbylephosphite, avec entre 9,1 pour cent en poids et 99,9 pour cent en poids d'au moins un dispersant succinique substitué d'hydrocarbyle sélectionné parmi le groupe constitué en un ester succinique d'un polyole, substitué d'hydrocarbyle, et d'un mélange d'un ester succinique d'un polyole, substitué d'hydrocarbyle, avec un bissuccinimide d'hydrocarbyle, le substituant d'hydrocarbyle ayant au moins 50 atomes de carbone, en l'absence d'amine éthoxylée et d'amide primaire d'un acide carboxylique à longue chaine.
- Procédé de préparation d'une composition d'huile lubrifiante selon la revendication 6, comprenant :le mélange d'entre 0,11 pour cent en poids et de 11,0 pour cent en poids de la composition d'additif anti-vibratoire selon une quelconque des revendications 1 à 5 avec supérieur à à 50 pour cent en poids d'une huile à viscosité lubrifiante, sur la base du poids total de la composition d'huile lubrifiante.
- Procédé pour réduire les vibrations dans une transmission comprenant :(a) mélanger une huile à viscosité lubrifiante avec une composition d'additif anti-vibratoire selon la revendication 1 pour former une composition d'huile lubrifiante, où l'additif anti-vibratoire est présent dans la composition d'huile lubrifiante dans un intervalle entre 0,11 pour cent en poids et de 11,0 pour cent en poids sur la base du poids total de la composition d'huile lubrifiante, et sous réserve que, si la composition d'huile lubrifiante comprend en plus un monosuccinimide, alors le rapport en poids entre le dispersant succinique substitué d'hydrocarbyle et monosuccinimide est au moins 7:3 ; et(b) ajouter le mélange de (a) à la transmission.
- Procédé pour réduire les vibrations selon la revendication 14, dans laquelle la composition d'huile lubrifiante contient en plus un monosuccinimide et le rapport en poids entre le dispersant succinique substitué d'hydrocarbyle et mono-succinimide est au moins 7,5:2,5.
- Procédé pour réduire les vibrations selon la revendication 15, dans laquelle la composition d'huile lubrifiante contient en plus un monosuccinimide et le rapport en poids entre le dispersant succinique substitué d'hydrocarbyle et mono-succinimide est au moins 8:2.
- Procédé pour réduire les vibrations selon la revendication 16, dans laquelle la composition d'huile lubrifiante contient en plus un monosuccinimide et le rapport en poids entre le dispersant succinique substitué d'hydrocarbyle et mono-succinimide est au moins 9:1.
- Procédé pour réduire les vibrations selon la revendication 14, dans laquelle la transmission est une transmission automatique ou une transmission à variation continue.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/021,166 US20060135375A1 (en) | 2004-12-21 | 2004-12-21 | Anti-shudder additive composition and lubricating oil composition containing the same |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| EP1674557A2 EP1674557A2 (fr) | 2006-06-28 |
| EP1674557A3 EP1674557A3 (fr) | 2010-10-27 |
| EP1674557B1 true EP1674557B1 (fr) | 2016-12-21 |
Family
ID=36202531
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP05257367.2A Active EP1674557B1 (fr) | 2004-12-21 | 2005-11-30 | Composition d'additif anti-vibratoire et composition d'huile lubrifiante la contenante |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US20060135375A1 (fr) |
| EP (1) | EP1674557B1 (fr) |
| JP (2) | JP5656336B2 (fr) |
| CA (1) | CA2530846C (fr) |
| SG (2) | SG123702A1 (fr) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4601315B2 (ja) | 2004-03-31 | 2010-12-22 | 出光興産株式会社 | ディーゼルエンジン用潤滑油組成物 |
| JP2007169570A (ja) * | 2005-12-26 | 2007-07-05 | Chevron Japan Ltd | 潤滑油組成物 |
| US20080128322A1 (en) * | 2006-11-30 | 2008-06-05 | Chevron Oronite Company Llc | Traction coefficient reducing lubricating oil composition |
| JP5184214B2 (ja) * | 2008-05-27 | 2013-04-17 | Ｊｘ日鉱日石エネルギー株式会社 | 金属ベルト式無段変速機用潤滑油組成物 |
| CN104250579B (zh) * | 2013-06-28 | 2016-09-28 | 中国石油化工股份有限公司 | 一种atf-iii自动传动液组合物 |
| JP2022550549A (ja) * | 2019-10-07 | 2022-12-02 | クローダ，インコーポレイティド | 腐食抑制 |
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-
2004
- 2004-12-21 US US11/021,166 patent/US20060135375A1/en not_active Abandoned
-
2005
- 2005-11-30 EP EP05257367.2A patent/EP1674557B1/fr active Active
- 2005-12-08 SG SG200507916A patent/SG123702A1/en unknown
- 2005-12-08 SG SG200805139-3A patent/SG144917A1/en unknown
- 2005-12-19 CA CA2530846A patent/CA2530846C/fr active Active
- 2005-12-20 JP JP2005367023A patent/JP5656336B2/ja active Active
-
2013
- 2013-07-29 JP JP2013156848A patent/JP2013216916A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| EP1674557A2 (fr) | 2006-06-28 |
| CA2530846C (fr) | 2015-07-14 |
| SG123702A1 (en) | 2006-07-26 |
| EP1674557A3 (fr) | 2010-10-27 |
| JP2006176776A (ja) | 2006-07-06 |
| JP2013216916A (ja) | 2013-10-24 |
| CA2530846A1 (fr) | 2006-06-21 |
| JP5656336B2 (ja) | 2015-01-21 |
| US20060135375A1 (en) | 2006-06-22 |
| SG144917A1 (en) | 2008-08-28 |
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