EP0323403A2 - Composition lubrifiante - Google Patents

Composition lubrifiante Download PDF

Info

Publication number: EP0323403A2
Authority: EP; European Patent Office
Prior art keywords: tert; alkyl; carbon atoms; compounds; series
Prior art date: 1987-12-24
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 Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Withdrawn

Application number

EP88810865A

Other languages

German (de)

English (en)

Other versions

EP0323403A3 (fr

Inventor

Samuel Dr. Evans

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Novartis AG

Original Assignee

Ciba Geigy AG

Priority date (The priority date 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 date listed.)

1987-12-24

Filing date

1988-12-15

Publication date

1989-07-05

1988-12-15 Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG

1989-07-05 Publication of EP0323403A2 publication Critical patent/EP0323403A2/fr

1989-10-11 Publication of EP0323403A3 publication Critical patent/EP0323403A3/fr

Status Withdrawn legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims abstract description 74
239000000314 lubricant Substances 0.000 title claims abstract description 26
150000001875 compounds Chemical class 0.000 claims abstract description 85
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 50
125000000217 alkyl group Chemical group 0.000 claims abstract description 39
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 18
239000012530 fluid Substances 0.000 claims abstract description 12
229910052717 sulfur Inorganic materials 0.000 claims abstract description 8
125000002947 alkylene group Chemical group 0.000 claims abstract description 5
229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
-1 2-methylfuryl Chemical group 0.000 claims description 47
DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims description 22
GQBHYWDCHSZDQU-UHFFFAOYSA-N 4-(2,4,4-trimethylpentan-2-yl)-n-[4-(2,4,4-trimethylpentan-2-yl)phenyl]aniline Chemical compound C1=CC(C(C)(C)CC(C)(C)C)=CC=C1NC1=CC=C(C(C)(C)CC(C)(C)C)C=C1 GQBHYWDCHSZDQU-UHFFFAOYSA-N 0.000 claims description 16
239000011541 reaction mixture Substances 0.000 claims description 15
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 12
OSFOTMWFXQGWKZ-UHFFFAOYSA-N n-phenyl-4-(2,4,4-trimethylpentan-2-yl)aniline Chemical compound C1=CC(C(C)(C)CC(C)(C)C)=CC=C1NC1=CC=CC=C1 OSFOTMWFXQGWKZ-UHFFFAOYSA-N 0.000 claims description 8
238000002156 mixing Methods 0.000 claims description 7
125000001424 substituent group Chemical group 0.000 claims description 7
125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 6
239000003963 antioxidant agent Substances 0.000 claims description 6
125000000753 cycloalkyl group Chemical group 0.000 claims description 6
125000002541 furyl group Chemical group 0.000 claims description 6
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 5
UOMXLEWVJZEVGP-UHFFFAOYSA-N 4-tert-butyl-n-phenylaniline Chemical compound C1=CC(C(C)(C)C)=CC=C1NC1=CC=CC=C1 UOMXLEWVJZEVGP-UHFFFAOYSA-N 0.000 claims description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
229910052794 bromium Inorganic materials 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
229910052731 fluorine Inorganic materials 0.000 claims description 4
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
OPEKHRGERHDLRK-UHFFFAOYSA-N 4-tert-butyl-n-(4-tert-butylphenyl)aniline Chemical compound C1=CC(C(C)(C)C)=CC=C1NC1=CC=C(C(C)(C)C)C=C1 OPEKHRGERHDLRK-UHFFFAOYSA-N 0.000 claims description 3
230000003078 antioxidant effect Effects 0.000 claims description 3
125000003944 tolyl group Chemical group 0.000 claims description 3
125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 2
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
239000003921 oil Substances 0.000 abstract description 15
239000002480 mineral oil Substances 0.000 abstract description 13
238000010525 oxidative degradation reaction Methods 0.000 abstract description 4
235000019198 oils Nutrition 0.000 description 14
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
239000000654 additive Substances 0.000 description 8
239000003054 catalyst Substances 0.000 description 7
238000000034 method Methods 0.000 description 7
235000010446 mineral oil Nutrition 0.000 description 7
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
150000002148 esters Chemical class 0.000 description 6
239000007788 liquid Substances 0.000 description 6
229910052757 nitrogen Inorganic materials 0.000 description 6
FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical group CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 description 5
239000002253 acid Substances 0.000 description 4
GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
239000010802 sludge Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
239000003381 stabilizer Substances 0.000 description 4
238000012360 testing method Methods 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
125000001931 aliphatic group Chemical group 0.000 description 3
238000004821 distillation Methods 0.000 description 3
238000005461 lubrication Methods 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
239000002184 metal Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
239000011593 sulfur Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
238000012065 two one-sided test Methods 0.000 description 3
ZQMPWXFHAUDENN-UHFFFAOYSA-N 1,2-bis[(2-methylphenyl)amino]ethane Natural products CC1=CC=CC=C1NCCNC1=CC=CC=C1C ZQMPWXFHAUDENN-UHFFFAOYSA-N 0.000 description 2
YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
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 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
XUQNLOIVFHUMTR-UHFFFAOYSA-N 2-[[2-hydroxy-5-nonyl-3-(1-phenylethyl)phenyl]methyl]-4-nonyl-6-(1-phenylethyl)phenol Chemical compound OC=1C(C(C)C=2C=CC=CC=2)=CC(CCCCCCCCC)=CC=1CC(C=1O)=CC(CCCCCCCCC)=CC=1C(C)C1=CC=CC=C1 XUQNLOIVFHUMTR-UHFFFAOYSA-N 0.000 description 2
WPMYUUITDBHVQZ-UHFFFAOYSA-N 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoic acid Chemical compound CC(C)(C)C1=CC(CCC(O)=O)=CC(C(C)(C)C)=C1O WPMYUUITDBHVQZ-UHFFFAOYSA-N 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 2
KEQFTVQCIQJIQW-UHFFFAOYSA-N N-Phenyl-2-naphthylamine Chemical compound C=1C=C2C=CC=CC2=CC=1NC1=CC=CC=C1 KEQFTVQCIQJIQW-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
239000011575 calcium Substances 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
229920001577 copolymer Polymers 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
239000003112 inhibitor Substances 0.000 description 2
JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 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
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
229910052698 phosphorus Inorganic materials 0.000 description 2
239000011574 phosphorus Substances 0.000 description 2
229920000193 polymethacrylate Polymers 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
239000000047 product Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
238000003756 stirring Methods 0.000 description 2
150000005846 sugar alcohols Polymers 0.000 description 2
239000010689 synthetic lubricating oil Substances 0.000 description 2
YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 2
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
WBSRIXCTCFFHEF-UHFFFAOYSA-N (3,5-ditert-butyl-4-hydroxyphenyl)methyl-ethoxyphosphinic acid Chemical compound CCOP(O)(=O)CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 WBSRIXCTCFFHEF-UHFFFAOYSA-N 0.000 description 1
125000006702 (C1-C18) alkyl group Chemical group 0.000 description 1
ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
VNQNXQYZMPJLQX-UHFFFAOYSA-N 1,3,5-tris[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-1,3,5-triazinane-2,4,6-trione Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CN2C(N(CC=3C=C(C(O)=C(C=3)C(C)(C)C)C(C)(C)C)C(=O)N(CC=3C=C(C(O)=C(C=3)C(C)(C)C)C(C)(C)C)C2=O)=O)=C1 VNQNXQYZMPJLQX-UHFFFAOYSA-N 0.000 description 1
150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
BBRHQNMMUUMVDE-UHFFFAOYSA-N 1-n,2-n-diphenylpropane-1,2-diamine Chemical compound C=1C=CC=CC=1NC(C)CNC1=CC=CC=C1 BBRHQNMMUUMVDE-UHFFFAOYSA-N 0.000 description 1
JUHXTONDLXIGGK-UHFFFAOYSA-N 1-n,4-n-bis(5-methylheptan-3-yl)benzene-1,4-diamine Chemical compound CCC(C)CC(CC)NC1=CC=C(NC(CC)CC(C)CC)C=C1 JUHXTONDLXIGGK-UHFFFAOYSA-N 0.000 description 1
ZJNLYGOUHDJHMG-UHFFFAOYSA-N 1-n,4-n-bis(5-methylhexan-2-yl)benzene-1,4-diamine Chemical compound CC(C)CCC(C)NC1=CC=C(NC(C)CCC(C)C)C=C1 ZJNLYGOUHDJHMG-UHFFFAOYSA-N 0.000 description 1
BJLNXEQCTFMBTH-UHFFFAOYSA-N 1-n,4-n-di(butan-2-yl)-1-n,4-n-dimethylbenzene-1,4-diamine Chemical compound CCC(C)N(C)C1=CC=C(N(C)C(C)CC)C=C1 BJLNXEQCTFMBTH-UHFFFAOYSA-N 0.000 description 1
APTGHASZJUAUCP-UHFFFAOYSA-N 1-n,4-n-di(octan-2-yl)benzene-1,4-diamine Chemical compound CCCCCCC(C)NC1=CC=C(NC(C)CCCCCC)C=C1 APTGHASZJUAUCP-UHFFFAOYSA-N 0.000 description 1
ZRMMVODKVLXCBB-UHFFFAOYSA-N 1-n-cyclohexyl-4-n-phenylbenzene-1,4-diamine Chemical compound C1CCCCC1NC(C=C1)=CC=C1NC1=CC=CC=C1 ZRMMVODKVLXCBB-UHFFFAOYSA-N 0.000 description 1
GFVSLJXVNAYUJE-UHFFFAOYSA-N 10-prop-2-enylphenothiazine Chemical compound C1=CC=C2N(CC=C)C3=CC=CC=C3SC2=C1 GFVSLJXVNAYUJE-UHFFFAOYSA-N 0.000 description 1
WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
UUAIOYWXCDLHKT-UHFFFAOYSA-N 2,4,6-tricyclohexylphenol Chemical compound OC1=C(C2CCCCC2)C=C(C2CCCCC2)C=C1C1CCCCC1 UUAIOYWXCDLHKT-UHFFFAOYSA-N 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
FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 1
LXWZXEJDKYWBOW-UHFFFAOYSA-N 2,4-ditert-butyl-6-[(3,5-ditert-butyl-2-hydroxyphenyl)methyl]phenol Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)C)C(C)(C)C)O)=C1O LXWZXEJDKYWBOW-UHFFFAOYSA-N 0.000 description 1
DXCHWXWXYPEZKM-UHFFFAOYSA-N 2,4-ditert-butyl-6-[1-(3,5-ditert-butyl-2-hydroxyphenyl)ethyl]phenol Chemical compound C=1C(C(C)(C)C)=CC(C(C)(C)C)=C(O)C=1C(C)C1=CC(C(C)(C)C)=CC(C(C)(C)C)=C1O DXCHWXWXYPEZKM-UHFFFAOYSA-N 0.000 description 1
CZNRFEXEPBITDS-UHFFFAOYSA-N 2,5-bis(2-methylbutan-2-yl)benzene-1,4-diol Chemical compound CCC(C)(C)C1=CC(O)=C(C(C)(C)CC)C=C1O CZNRFEXEPBITDS-UHFFFAOYSA-N 0.000 description 1
JZODKRWQWUWGCD-UHFFFAOYSA-N 2,5-di-tert-butylbenzene-1,4-diol Chemical compound CC(C)(C)C1=CC(O)=C(C(C)(C)C)C=C1O JZODKRWQWUWGCD-UHFFFAOYSA-N 0.000 description 1
SLUKQUGVTITNSY-UHFFFAOYSA-N 2,6-di-tert-butyl-4-methoxyphenol Chemical compound COC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SLUKQUGVTITNSY-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
FRAQIHUDFAFXHT-UHFFFAOYSA-N 2,6-dicyclopentyl-4-methylphenol Chemical compound OC=1C(C2CCCC2)=CC(C)=CC=1C1CCCC1 FRAQIHUDFAFXHT-UHFFFAOYSA-N 0.000 description 1
JBYWTKPHBLYYFJ-UHFFFAOYSA-N 2,6-ditert-butyl-4-(2-methylpropyl)phenol Chemical compound CC(C)CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 JBYWTKPHBLYYFJ-UHFFFAOYSA-N 0.000 description 1
SAJFQHPVIYPPEY-UHFFFAOYSA-N 2,6-ditert-butyl-4-(dioctadecoxyphosphorylmethyl)phenol Chemical compound CCCCCCCCCCCCCCCCCCOP(=O)(OCCCCCCCCCCCCCCCCCC)CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SAJFQHPVIYPPEY-UHFFFAOYSA-N 0.000 description 1
SCXYLTWTWUGEAA-UHFFFAOYSA-N 2,6-ditert-butyl-4-(methoxymethyl)phenol Chemical compound COCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SCXYLTWTWUGEAA-UHFFFAOYSA-N 0.000 description 1
UDFARPRXWMDFQU-UHFFFAOYSA-N 2,6-ditert-butyl-4-[(3,5-ditert-butyl-4-hydroxyphenyl)methylsulfanylmethyl]phenol Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CSCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 UDFARPRXWMDFQU-UHFFFAOYSA-N 0.000 description 1
VMZVBRIIHDRYGK-UHFFFAOYSA-N 2,6-ditert-butyl-4-[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 VMZVBRIIHDRYGK-UHFFFAOYSA-N 0.000 description 1
LBOGPIWNHXHYHN-UHFFFAOYSA-N 2-(2-hydroxy-5-octylphenyl)sulfanyl-4-octylphenol Chemical compound CCCCCCCCC1=CC=C(O)C(SC=2C(=CC=C(CCCCCCCC)C=2)O)=C1 LBOGPIWNHXHYHN-UHFFFAOYSA-N 0.000 description 1
NISAHDHKGPWBEM-UHFFFAOYSA-N 2-(4-nonylphenoxy)acetic acid Chemical compound CCCCCCCCCC1=CC=C(OCC(O)=O)C=C1 NISAHDHKGPWBEM-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
XRMBCKBVKSPUJX-UHFFFAOYSA-N 2-[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-8-methyl-2-sulfanylnonanoic acid Chemical compound CC(C)CCCCCC(S)(C(O)=O)CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 XRMBCKBVKSPUJX-UHFFFAOYSA-N 0.000 description 1
UTNMPUFESIRPQP-UHFFFAOYSA-N 2-[(4-aminophenyl)methyl]aniline Chemical compound C1=CC(N)=CC=C1CC1=CC=CC=C1N UTNMPUFESIRPQP-UHFFFAOYSA-N 0.000 description 1
AKNMPWVTPUHKCG-UHFFFAOYSA-N 2-cyclohexyl-6-[(3-cyclohexyl-2-hydroxy-5-methylphenyl)methyl]-4-methylphenol Chemical compound OC=1C(C2CCCCC2)=CC(C)=CC=1CC(C=1O)=CC(C)=CC=1C1CCCCC1 AKNMPWVTPUHKCG-UHFFFAOYSA-N 0.000 description 1
VSFWPWFQAPMUED-UHFFFAOYSA-N 2-sulfanyl-3h-thiadiazole-5-thiol Chemical compound SN1NC=C(S)S1 VSFWPWFQAPMUED-UHFFFAOYSA-N 0.000 description 1
WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 1
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LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
125000001400 nonyl 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])[H] 0.000 description 1
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
125000002347 octyl 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])[H] 0.000 description 1
NTTIENRNNNJCHQ-UHFFFAOYSA-N octyl n-(3,5-ditert-butyl-4-hydroxyphenyl)carbamate Chemical compound CCCCCCCCOC(=O)NC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NTTIENRNNNJCHQ-UHFFFAOYSA-N 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000002918 oxazolines Chemical class 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
210000002741 palatine tonsil Anatomy 0.000 description 1
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
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
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
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
150000004707 phenolate Chemical class 0.000 description 1
239000002530 phenolic antioxidant Substances 0.000 description 1
229950000688 phenothiazine Drugs 0.000 description 1
150000003014 phosphoric acid esters Chemical class 0.000 description 1
229920000233 poly(alkylene oxides) Polymers 0.000 description 1
229920000058 polyacrylate Polymers 0.000 description 1
229920001515 polyalkylene glycol Polymers 0.000 description 1
229920013639 polyalphaolefin Polymers 0.000 description 1
229920001083 polybutene Polymers 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
229920000151 polyglycol Polymers 0.000 description 1
239000010695 polyglycol Substances 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
229920001343 polytetrafluoroethylene Polymers 0.000 description 1
239000004810 polytetrafluoroethylene Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
238000005070 sampling Methods 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
COEZWFYORILMOM-UHFFFAOYSA-M sodium 4-[(2,4-dihydroxyphenyl)diazenyl]benzenesulfonate Chemical compound [Na+].OC1=CC(O)=CC=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 COEZWFYORILMOM-UHFFFAOYSA-M 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000001593 sorbitan monooleate Substances 0.000 description 1
229940035049 sorbitan monooleate Drugs 0.000 description 1
235000011069 sorbitan monooleate Nutrition 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
238000003860 storage Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
238000010998 test method Methods 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
UVZICZIVKIMRNE-UHFFFAOYSA-N thiodiacetic acid Chemical compound OC(=O)CSCC(O)=O UVZICZIVKIMRNE-UHFFFAOYSA-N 0.000 description 1
235000019303 thiodipropionic acid Nutrition 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1
125000002889 tridecyl 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])[H] 0.000 description 1
125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
125000002948 undecyl 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])[H] 0.000 description 1
238000003828 vacuum filtration Methods 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Classifications

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- C10M2215/067—Polyaryl amine alkanes
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- 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
- C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
- C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
- C10M2219/108—Phenothiazine
- 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
- C10N2040/08—Hydraulic fluids, e.g. brake-fluids

Definitions

the present invention relates to new lubricant and hydraulic fluid compositions with high stability against oxidative degradation.
additives from the series of diphenylamines as described in EP-A-0 149 422, are added to the lubricating oils, for example.
New lubricant compositions have now been found which have further improved properties compared to the previously known products and are distinguished by high stability against oxidative degradation.
the present invention relates to a composition
a composition comprising at least one lubricant, in particular based on mineral oil, synthetic oils or mixtures thereof, or a hydraulic fluid, and a mixture of one or more compounds from the series A) and one or more compounds from the series B.
the compounds of series A) having the general formula have in which R1 and R1 'are the same or different and -H, alkyl having 1 to 24 carbon atoms, cycloalkyl having 5 to 12 carbon atoms or phenyl- (C1-C4) alkyl and n is a number from 0 , 1 or 2 means and the compounds of series B) the general formula have in which R2 -H, alkyl having 1 to 24 carbon atoms, phenyl, substituted with NO2, Cl, Br, F, C1-C12-alkyl and / or C1-C12-alkoxy phenyl, phenyl- (C1-C4 ) alkyl, phenyl of the general formula wherein R6 -H, alkyl having 1 to 20 C atoms or phenyl- (C1-C4) alkyl and x is 1 or 2, or R2 means furyl, tetrahydrofuryl, 2-methylfuryl, 2-methylte
substituents R1, R1 ′, R2, R3 or R5 are alkyl having 1 to 24 carbon atoms, these are, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, 2-butyl, t-butyl, pentyl, 1- Methylphenyl, isopentyl, hexyl, 1,3-dimethylbutyl, heptyl, 1,1,3,3-tetramethylbutyl, 1-methylhexyl, 3-heptyl, octyl, 2-ethylhexyl, 1-methylheptyl, nonyl, 1,1,3- Trimethylhexyl, decyl, undecyl, dodecyl, 1-methylundecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octa
R1 or R1 'cycloalkyl having 5 to 12 carbon atoms it is about a group of the formula where a is a number from 3 to 9.
This cycloalkyl group can optionally be substituted by C1-C4-alkyl. Examples are cyclopentyl, cyclohexyl, methylcyclohexyl, dimethylcyclohexyl, trimethylcyclohexyl, t-butylcyclohexyl, cyclooctyl and cyclododecyl.
the substituent phenyl- (C1-C4) alkyl is preferably benzyl.
R2 or R3 can represent a phenyl substituted by C1-C12-alkyl.
C1-C12 alkyl can be taken from the above list. Examples are methylphenyl, dimethylphenyl, trimethylphenyl, ethylphenyl, t-butylphenyl, isopropylphenyl, di-t-butylphenyl or 2,6-di-t-butyl-4-methylphenyl.
R4 'in formula (IIa) can mean unsubstituted or C1-C18 alkyl substituted alkylene.
Examples include methylene, ethylene, propylene, trimethylene, tetramethylene, pentamethylene, hexamethylene, heptamethylene, octamethylene, decamethylene or dodecamethylene, furthermore di-1,1-dimethyl-2,2-dimethyldimethylene, 1,1,2-trimethyl-2- n-propyltrimethylene, 2-ethyl-2-n-butyltrimethylene, 1-iso-propyl-2,2-dimethyltrimethylene, 1-methyltrimethylene, 2,2-dimethyltrimethylene, 1,1,3-trimethylene or 2,2,4- or 2,4,4-trimethylhexamethylene.
R4 ' represents dimethylene or trimethylene.
R1 and R1 ' are the same or different in the compounds of the formula I and are -H, alkyl having 4 to 12 carbon atoms, cycloalkyl and preferably cyclohexyl, or phenyl- (C1-C4) alkyl.
R1 and R1 ' represent -H or alkyl having 4 to 8 carbon atoms.
reaction products can be used as compounds of series A) obtainable by the method according to EP-A-0 149 422 can be used.
the reaction product produced by the process mentioned is preferably used as such.
diphenylamine is reacted with diisobutylene in the presence of a catalyst to form a liquid antioxidant composition such that the reaction of diphenylamine with an excess of diisobutylene is carried out in the presence of an active alumina catalyst such that the concentration of diisobutylene over the reaction period in the It is kept essentially constant that the reaction temperature is at least 160 ° C., that the reaction is carried out until the 4,4′-di-tert-octyldiphenylamine content, based on the reaction mass without catalyst, is below 30% by weight, preferably below 25% by weight and the diphenylamine content below 10% by weight, preferably below 5% by weight, that the catalyst and unreacted diisobutylene are removed and that the resulting liquid product is isolated.
This process results in a liquid reaction mixture containing 4,4'-di-tert-ocytyldiphenylamine.
This reaction mixture comprising the compounds from the series A), is preferably used for the mixture together with the compounds from the series B), as mentioned.
This mixture can be obtained in particular by the process mentioned.
R4 denotes alkyl having 4 to 12 carbon atoms, phenyl or - (CH2) -OR5, where R5 is alkyl with 1 to 18 carbon atoms and preferably for alkyl with 8-13 carbon atoms and s is 1 or 2.
the very particularly preferred compounds of the formula II include those in which R2 is -H, alkyl having 1 to 8 C atoms, furyl or phenyl, then compounds in which R3 -H, alkyl having 1 to 8 C atoms or where R4 has the meaning given above.
R4 preferably has the meaning of alkyl having 8 to 12 carbon atoms or -CH2- -OR5, wherein R5 is branched alkyl having 8 to 13 carbon atoms and in particular tert-butyl or 2-ethylhexyl.
Compounds from series B) can be used as individual compounds or as a mixture of different compounds from series B) with one another in each case in a mixture with a compound from series A) or a mixture of compounds from series A).
the lubricant composition accordingly contains a mixture of at least one compound from the series A) with the formula I and at least one compound from the series B) with the formula II.
Mixtures of 1 to 9 parts by weight of the compound or compounds of series A) with 9 to 1 parts by weight of the compound or compounds of series B), and preferably of 2 to 8 parts by weight of the compound or compounds of series A) and 8, are expedient up to 2 parts by weight of the compound or the compounds of series B) applied.
Mixtures are preferably also used, comprising as compounds of series A) a reaction mixture containing 4,4'-di-tert-octyldiphenylamine and as compounds of series B), a compound of the formula where i-C8H17 is a mixture of branched isomers each having 8 carbon atoms, in a mixing ratio of A) to B) from 9: 1 to 1: 1 parts by weight.
the mixing ratio of A) to B) is 9: 1 or 7: 3 or 1: 1 parts by weight.
a preferred mixture contains as compounds of series A) a reaction mixture containing 4,4'-di-tert-octyldiphenylamine and, as a compound of series B), a compound of the formula where i-C8H17 is a mixture of branched isomers each having 8 carbon atoms, in a mixing ratio of A) to B) from 9: 1 to 1: 9 parts by weight.
the mixing ratio of A) to B) is 9: 1 or 3: 7 or 1: 9 parts by weight.
the compounds of formula II are for example from Reid, "Organic Chemistry of Bivalent Sulfur", vol. 3, pp. 320-341, Chemical Publishing Company, New York, 1960, and can be synthesized in a manner known per se.
the following reaction routes are available, for example: this method can be carried out without a solvent or in a solvent, for example in cyclohexane, toluene, xylene or nitro or chlorobenzene.
the process can be carried out either without the presence of a solvent or e.g. perform in methanol, ethanol, hexane or toluene as the solvent.
the mixture according to the invention is suitable for adding lubricants, in particular those based on mineral oils, synthetic oils or semi-synthetic lubricating oils and hydraulic fluids.
the lubricant can thus be, for example, an oil based on a mineral oil or a synthetic oil, or a fat.
mineral oil includes all mineral oils for lubrication purposes, such as hydrocarbon-based mineral oils.
Synthetic oils can be, for example, aliphatic or aromatic carboxyl esters, polymeric esters, polyalkylene oxides, phosphoric acid esters, poly- ⁇ -olefins, silicones, glycols, polyglycols or polyalkylene glycols.
the lubricants can additionally contain other additives which are added in order to further improve the basic properties of lubricants; these include: other antioxidants, metal passivators, rust inhibitors, viscosity index improvers, pour point depressants, dispersants, detergents, thickeners, biocides, anti-foaming agents, demulsifiers and emulsifiers, as well as high-pressure additives and friction reducers.
additives which are added in order to further improve the basic properties of lubricants; these include: other antioxidants, metal passivators, rust inhibitors, viscosity index improvers, pour point depressants, dispersants, detergents, thickeners, biocides, anti-foaming agents, demulsifiers and emulsifiers, as well as high-pressure additives and friction reducers.
2,6-di-tert-butyl-4-methylphenol 2,6-di-tert-butylphenol, 2-tert-butyl-4,6-dimethylphenol, 2,6-di-tert-butyl-4-ethylphenol, 2,6-di-tert-butyl-4-n-butylphenol, 2,6-di-tert-butyl-4-iso-butylphenol, 2,6-di-cyclopentyl4-methylphenol, 2- ( ⁇ -methylcyclohexyl) - 4,6-dimethylphenol, 2,6-di-octadecyl-4-methylphenol, 2,4,6-tri-cyclohexylphenol, 2,6-di-tert-butyl-4-methoxymethylphenol, o-tert-butylphenol.
esters of ⁇ - (3,5-di-tert-butyl-4-hydroxyphenyl) propionic acid with mono- or polyhydric alcohols e.g.
Methanol diethylene glycol, octadecanol, triethylene glycol, 1,6-hexanediol, pentaerythritol, neopentyl glycol, tris-hydroxyethyl isocyanurate, thiodiethylene glycol, bis-hydroxyethyl oxalic acid diamide.
esters of ⁇ - (5-tert-butyl-4-hydroxy-3-methylphenyl) propionic acid with mono- or polyhydric alcohols e.g.
Methanol diethylene glycol, octadecanol, triethylene glycol, 1,6-hexanediol, pentaerythritol, neopentyl glycol, tris-hydroxyethyl isocyanurate, thiodiethylene glycol, di-hydroxyethyl oxalic acid diamide.
Aliphatic or aromatic phosphites esters of thiodipropionic acid or thiodiacetic acid, or salts of dithiocarbamide or dithiophosphoric acid.
metal passivators examples are:
Triazoles for copper, for example: Triazoles, benzotriazoles and their derivatives, 2-mercaptobenzothiazole, 5,5'-methylenebisbenztriazole, 4,5,6,7-tetrahydrobenzetriazole, 2,5-di-mercaptothiadiazole, salicylidene-propylenediamine, salts of salicylaminoguanidine.
rust inhibitors are:
viscosity index improvers examples are:
Polyacrylates polymethacrylates, vinyl pyrrolidone / methacrylate copolymers, polyvinyl pyrrolidones, polybutenes, olefin copolymers, styrene / acrylate copolymers, polyethers.
pour point low mixers are:
dispersants / surfactants examples are:
Polybutenylsuccinic acid imides polybutenylphosphonic acid derivatives, basic magnesium, calcium and barium sulfonates and phenolates.
wear protection additives are:
Compounds containing sulfur and / or phosphorus and / or halogen such as sulfurized vegetable oils, zinc dialkyldithiophosphates, tritolyl phosphate, chlorinated paraffins, alkyl and aryl disulfides, triphenylphosphorothionates, diethanolaminomethyltolyltriazole and di (2-isooctyl) aminomethyltolyl.
the invention also encompasses the use of mixtures of compounds of series B) as an antioxidant in lubricants and hydraulic fluids.
the additives according to the invention are also effective in lubrication systems of the type described above, but which additionally have a co-lubrication system which contains customary amounts of solid lubricants, such as graphite, boron nitride, molybdenum disulfide or polytetrafluoroethylene.
solid lubricants such as graphite, boron nitride, molybdenum disulfide or polytetrafluoroethylene.
the compounds of the series A) and the compounds of the series B) can be mixed with one another in the proportions indicated and the mixture can then be mixed in with the lubricant or the hydraulic fluid in the quantities mentioned. It is also expedient to mix the compounds of the series A) and the compounds of the series B) separately with the lubricant or the hydraulic fluid, the quantitative proportions given also having to be adhered to in this case. The production of so-called masterbatches is also possible.
the reaction mass is cooled to 60 ° C. and the catalyst is removed by vacuum filtration.
the filtrate is transferred to a distillation apparatus and the pressure is reduced to 26 mbar with heating and stirring.
the liquid has the approximate composition of 3.2% by weight diphenylamine, 13.2% by weight 4-tert-butyldiphenylamine, 25.3% by weight of compounds from the 4-tert-octyldiphenylamine series, 4.4 '-Di-tert-butylamine and 2,4,4'-tris-tert-butylamine, 24.2% by weight of compounds from the series 4-tert-butyl-4'-tert-octyldiphenylamine, 2.2' - or 2,4'-di-tert-octyldiphenylamine and 2,4-di-tert-butyl-4'tert-octyldiphenylamine and 18.2% by weight of 4,4'-di-tert-octyldiphenylamine and 6.0 Wt .-% 2,4-di-tert-octyl-4'-tert-butyldiphenylamine, as well as further shares in other higher alkyl
the thioketal compound according to a) and the reaction mixture according to b) are mixed with one another in the amounts evident from example 4. These latter mixtures are mixed in an amount of 0.25% by weight, based on the oil, of a mineral oil of the Mobil 15 SS4 type.
the thioketal compound according to a) and the reaction mixture according to b) are mixed with one another in the amounts evident from example 4. These latter mixtures are mixed in an amount of 0.25% by weight, based on the oil, of a mineral oil of the Mobil 15 SS4 type.
the compounds according to a) and the reaction mixture according to b) are combined in the proportions from a) to b) of 9: 1, 7: 3, 1: 1, 3: 7 and 1: 9 parts by weight and processed into corresponding mixtures.
the oil to be tested (Mobil 15 SS4) is heated to 95 ° C. in the presence of water, oxygen, an iron-copper catalyst and the stabilizer for 1000 hours.
the TAN acid value (in mg KOH consumption per g test oil) and the sludge (SLUDGE) (in mg residue per batch) are then determined.
the results are summarized in Table 1.
the concentration of the stabilizer mixtures is 0.25% by weight, based on the oil.
Table 2 below shows the measured values from the TOST test for various mixtures of compounds according to Example 3. The test procedure and conditions are given above, except for the test duration which is 500 hours and the oil (mineral oil BB).
Table 2 Example 4 Stabilizer (total 0.25% by weight) mixture of 500 hours TOST % By weight according to the example % By weight according to the example TAN (mg KOH / g oil) SLUDGE (mg) G) 10 3a) 90 3b) 0.24 58 H) 30 3a) 70 3b) 0.25 38 i) 50 3a) 50 3b) 0.11 14 k) 70 3a) 30 3b) 0.08 27th l) 90 3a) 10 3b) 0.08 87

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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)

EP88810865A 1987-12-24 1988-12-15 Composition lubrifiante Withdrawn EP0323403A3 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH5055/87		1987-12-24
CH505587		1987-12-24

Publications (2)

Publication Number	Publication Date
EP0323403A2 true EP0323403A2 (fr)	1989-07-05
EP0323403A3 EP0323403A3 (fr)	1989-10-11

Family

ID=4287208

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
EP88810865A Withdrawn EP0323403A3 (fr)	1987-12-24	1988-12-15	Composition lubrifiante

Country Status (3)

Country	Link
US (1)	US4963276A (fr)
EP (1)	EP0323403A3 (fr)
JP (1)	JPH01203499A (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0346283A3 (en) *	1988-06-09	1990-03-28	Ciba-Geigy Ag	Lubricant composition

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5595963A (en) *	1994-12-05	1997-01-21	Exxon Chemical Patents Inc.	Synergistic antioxidant combinations for lubricating oils

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3041284A (en) *	1957-12-02	1962-06-26	Shell Oil Co	Lubricating compositions
US3944492A (en) *	1966-04-07	1976-03-16	Uniroyal, Inc.	Lubricant compositions containing N-substituted naphthylamines as antioxidants
US4058469A (en) *	1975-12-05	1977-11-15	The Lubrizol Corporation	Lubricants and functional fluids containing polyfunctional nitriles
US4248723A (en) *	1977-06-23	1981-02-03	Ciba-Geigy Corporation	Acetal derivatives as extreme pressure additives for lubricants
US4394279A (en) *	1981-08-07	1983-07-19	Chevron Research Company	Antioxidant combinations of sulfur containing molybdenum complexes and aromatic amine compounds for lubricating oils
GB8332797D0 (en) *	1983-12-08	1984-01-18	Ciba Geigy Ag	Antioxidant production
DE3586144D1 (de) *	1984-05-15	1992-07-09	Ciba Geigy Ag	Zusaetze fuer materialien.
US4704219A (en) *	1985-07-05	1987-11-03	The B. F. Goodrich Company	Novel composition of para-butylated and octylated, ortho-ethylated diphenylamines

1988
- 1988-12-15 US US07/284,568 patent/US4963276A/en not_active Expired - Fee Related
- 1988-12-15 EP EP88810865A patent/EP0323403A3/fr not_active Withdrawn
- 1988-12-24 JP JP63327512A patent/JPH01203499A/ja active Pending

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0346283A3 (en) *	1988-06-09	1990-03-28	Ciba-Geigy Ag	Lubricant composition
US5091099A (en) *	1988-06-09	1992-02-25	Ciba-Geigy Corporation	Lubricating oil composition

Also Published As

Publication number	Publication date
US4963276A (en)	1990-10-16
EP0323403A3 (fr)	1989-10-11
JPH01203499A (ja)	1989-08-16

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Publication	Publication Date	Title
EP0376889B1 (fr)	1993-05-19	Composition lubrifiante
EP0721979B1 (fr)	2002-04-17	Compositions lubrifiantes stabilisées
DE3446630C2 (de)	1995-08-10	Stabilisator-Systeme, deren Verwendung und diese enthaltende Schmierstoffe
EP0346283B1 (fr)	1992-07-29	Composition lubrifiante
EP0160620A2 (fr)	1985-11-06	Désactivateurs de métaux
DE68903468T2 (de)	1993-04-15	Schmiermittelzusammensetzungen.
EP0273868B1 (fr)	1992-07-08	Tétrahydroquinoléines N-substituées comme anti-oxydants pour lubrifiants
EP0432089A1 (fr)	1991-06-12	Compositions lubrifiantes
DE4200192A1 (de)	1992-07-09	Schmiermittelzusammensetzungen
EP0737684B1 (fr)	2003-11-12	Composés contenant des groupes (benzo)triazole, leur préparation et leur utilisation comme désactivateurs de métaux et inhibiteurs de corrosion
DE4317980B4 (de)	2007-03-22	Bis-Dithiophosphorsäurederivate als Schmiermitteladditive
EP0286595B1 (fr)	1993-08-11	Composés anti-oxydants contenant du sulfure pour lubrifiants et élastomères
EP0524145B1 (fr)	1999-01-27	Additifs multifonctionnels pour lubrifiants
EP0317513A2 (fr)	1989-05-24	Dérivés de mercaptotriazines comme additifs pour lubrifiants
EP0322362B1 (fr)	1991-05-08	Dérivés de thiadiazoles comme additifs pour lubrifiants
EP0368803B1 (fr)	1993-04-07	Composition lubrifiante
EP0323403A2 (fr)	1989-07-05	Composition lubrifiante
EP0595771B1 (fr)	1996-11-27	Additifs pour lubrifiants exempts de phosphore
EP0466639B1 (fr)	1994-08-10	Composition de lubrifiant
EP0480875B1 (fr)	1994-05-04	Composition de lubrifiant
DE69007214T2 (de)	1994-07-14	Butenylaromatische Aminstabilisatoren.
EP0595770B1 (fr)	1998-01-14	Nouveaux dithiophosphates comme additifs anti-usure
EP0682022B1 (fr)	2002-07-24	Produits de condensation de mélamine, de benzotriazoles et d'aldéhydes
EP0328488A2 (fr)	1989-08-16	Disulphides asymétriques dans des compositions lubrifiantes
EP0398215A1 (fr)	1990-11-22	Compositions lubrifiantes