EP0211806A2 - Additifs pour compositions lubrifiantes - Google Patents

Additifs pour compositions lubrifiantes Download PDF

Info

Publication number: EP0211806A2
Authority: EP; European Patent Office
Prior art keywords: alkyl; methyl; formula; atom; phenyl
Prior art date: 1985-07-30
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.): Granted

Application number

EP86810334A

Other languages

German (de)

English (en)

Other versions

EP0211806B1 (fr

EP0211806A3 (en

Inventor

Hugo Dr. Camenzind

Paul Dr. Dubs

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.)

1985-07-30

Filing date

1986-07-24

Publication date

1987-02-25

1986-07-24 Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG

1987-02-25 Publication of EP0211806A2 publication Critical patent/EP0211806A2/fr

1988-06-08 Publication of EP0211806A3 publication Critical patent/EP0211806A3/de

1990-01-24 Application granted granted Critical

1990-01-24 Publication of EP0211806B1 publication Critical patent/EP0211806B1/fr

2006-07-24 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

239000000654 additive Substances 0.000 title claims abstract description 11
239000000203 mixture Substances 0.000 title claims description 19
230000001050 lubricating effect Effects 0.000 title 1
-1 N-disubstituted S-thiiranyl-methylcarbamothioates Chemical class 0.000 claims abstract description 54
239000000314 lubricant Substances 0.000 claims abstract description 25
150000001875 compounds Chemical group 0.000 claims abstract description 21
229910052500 inorganic mineral Inorganic materials 0.000 claims abstract description 7
239000011707 mineral Substances 0.000 claims abstract description 6
125000000217 alkyl group Chemical group 0.000 claims description 19
125000004433 nitrogen atom Chemical group N* 0.000 claims description 16
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
125000004607 1,2,3,4-tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims description 7
125000003342 alkenyl group Chemical group 0.000 claims description 7
125000003710 aryl alkyl group Chemical group 0.000 claims description 6
125000000753 cycloalkyl group Chemical group 0.000 claims description 6
125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 6
125000001624 naphthyl group Chemical group 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
125000002757 morpholinyl group Chemical group 0.000 claims description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
125000003386 piperidinyl group Chemical group 0.000 claims description 5
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
125000001931 aliphatic group Chemical group 0.000 claims description 4
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
125000001424 substituent group Chemical group 0.000 claims description 4
125000004605 1,2,3,4-tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 3
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
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 3
125000000623 heterocyclic group Chemical group 0.000 claims description 3
PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 2
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
125000004434 sulfur atom Chemical group 0.000 claims description 2
125000004193 piperazinyl group Chemical group 0.000 claims 1
229910052757 nitrogen Inorganic materials 0.000 abstract description 17
239000003795 chemical substances by application Substances 0.000 abstract 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
150000002148 esters Chemical class 0.000 description 7
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 6
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
229910052751 metal Inorganic materials 0.000 description 5
239000002184 metal Substances 0.000 description 5
239000003921 oil Substances 0.000 description 5
235000019198 oils Nutrition 0.000 description 5
125000004043 oxo group Chemical group O=* 0.000 description 5
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 4
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 4
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
229910052698 phosphorus Inorganic materials 0.000 description 4
239000011574 phosphorus Substances 0.000 description 4
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 3
OBBMPCCOYZPQIZ-UHFFFAOYSA-N NC([O-])=[S+]CC1SC1 Chemical class NC([O-])=[S+]CC1SC1 OBBMPCCOYZPQIZ-UHFFFAOYSA-N 0.000 description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
125000004183 alkoxy alkyl group Chemical group 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
239000011575 calcium Substances 0.000 description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
239000003879 lubricant additive Substances 0.000 description 3
239000000243 solution Substances 0.000 description 3
229910052717 sulfur Inorganic materials 0.000 description 3
239000011593 sulfur Substances 0.000 description 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 2
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
NOALDENEOOTIED-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethanol;methanol Chemical compound OC.OCCOCCO NOALDENEOOTIED-UHFFFAOYSA-N 0.000 description 2
125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 2
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 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
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
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
239000003963 antioxidant agent Substances 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
238000002485 combustion reaction Methods 0.000 description 2
229920001577 copolymer Polymers 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-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
239000002270 dispersing agent Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
125000005842 heteroatom Chemical group 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
ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
KCTVZKPLKCEUJF-UHFFFAOYSA-N methylcarbamothioic s-acid Chemical compound CNC(S)=O KCTVZKPLKCEUJF-UHFFFAOYSA-N 0.000 description 2
IXHMTDIIQNIVBN-UHFFFAOYSA-N n'-(2,2-dihydroxyethyl)oxamide Chemical compound NC(=O)C(=O)NCC(O)O IXHMTDIIQNIVBN-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
125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([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
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
229920000193 polymethacrylate Polymers 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
231100000241 scar Toxicity 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
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
238000003756 stirring Methods 0.000 description 2
150000005846 sugar alcohols Polymers 0.000 description 2
239000000725 suspension 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
ZEBMSMUPGIOANU-UHFFFAOYSA-N (3,5-ditert-butyl-4-hydroxyphenyl)methylphosphonic acid Chemical compound CC(C)(C)C1=CC(CP(O)(O)=O)=CC(C(C)(C)C)=C1O ZEBMSMUPGIOANU-UHFFFAOYSA-N 0.000 description 1
WQXYSVHBMXNXTJ-UHFFFAOYSA-N (3-tert-butyl-4-hydroxyphenyl) butanoate Chemical compound CCCC(=O)OC1=CC=C(O)C(C(C)(C)C)=C1 WQXYSVHBMXNXTJ-UHFFFAOYSA-N 0.000 description 1
125000006552 (C3-C8) cycloalkyl 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
LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical group C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 1
BIGYLAKFCGVRAN-UHFFFAOYSA-N 1,3,4-thiadiazolidine-2,5-dithione Chemical compound S=C1NNC(=S)S1 BIGYLAKFCGVRAN-UHFFFAOYSA-N 0.000 description 1
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
WGCYRFWNGRMRJA-UHFFFAOYSA-N 1-ethylpiperazine Chemical group CCN1CCNCC1 WGCYRFWNGRMRJA-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
OBAYJNLUPHGFCT-UHFFFAOYSA-N 1-n,4-n-di(butan-2-yl)-1-n,4-n-dimethylbenzene-1,4-diamine;n-phenylaniline Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1.CCC(C)N(C)C1=CC=C(N(C)C(C)CC)C=C1 OBAYJNLUPHGFCT-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
125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 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
HEHFQKNEJQRBFJ-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol;hexane-1,6-diol Chemical compound OCCCCCCO.OCC(CO)(CO)CO HEHFQKNEJQRBFJ-UHFFFAOYSA-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
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
LKALLEFLBKHPTQ-UHFFFAOYSA-N 2,6-bis[(3-tert-butyl-2-hydroxy-5-methylphenyl)methyl]-4-methylphenol Chemical compound OC=1C(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=CC(C)=CC=1CC1=CC(C)=CC(C(C)(C)C)=C1O LKALLEFLBKHPTQ-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
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
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GIWKOZXJDKMGQC-UHFFFAOYSA-L lead(2+);naphthalene-2-carboxylate Chemical compound [Pb+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 GIWKOZXJDKMGQC-UHFFFAOYSA-L 0.000 description 1
239000010687 lubricating oil Substances 0.000 description 1
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000010688 mineral lubricating oil Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
125000001421 myristyl 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])[H] 0.000 description 1
FSWDLYNGJBGFJH-UHFFFAOYSA-N n,n'-di-2-butyl-1,4-phenylenediamine Chemical compound CCC(C)NC1=CC=C(NC(C)CC)C=C1 FSWDLYNGJBGFJH-UHFFFAOYSA-N 0.000 description 1
KEZPMZSDLBJCHH-UHFFFAOYSA-N n-(4-anilinophenyl)-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(C=C1)=CC=C1NC1=CC=CC=C1 KEZPMZSDLBJCHH-UHFFFAOYSA-N 0.000 description 1
KESXDDATSRRGAH-UHFFFAOYSA-N n-(4-hydroxyphenyl)butanamide Chemical compound CCCC(=O)NC1=CC=C(O)C=C1 KESXDDATSRRGAH-UHFFFAOYSA-N 0.000 description 1
JVKWTDRHWOSRFT-UHFFFAOYSA-N n-(4-hydroxyphenyl)dodecanamide Chemical compound CCCCCCCCCCCC(=O)NC1=CC=C(O)C=C1 JVKWTDRHWOSRFT-UHFFFAOYSA-N 0.000 description 1
VQLURHRLTDWRLX-UHFFFAOYSA-N n-(4-hydroxyphenyl)nonanamide Chemical compound CCCCCCCCC(=O)NC1=CC=C(O)C=C1 VQLURHRLTDWRLX-UHFFFAOYSA-N 0.000 description 1
YASWBJXTHOXPGK-UHFFFAOYSA-N n-(4-hydroxyphenyl)octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NC1=CC=C(O)C=C1 YASWBJXTHOXPGK-UHFFFAOYSA-N 0.000 description 1
IMXRBCGZTVENAC-UHFFFAOYSA-N n-phenyl-n-(2,4,4-trimethylpentan-2-yl)aniline Chemical class C=1C=CC=CC=1N(C(C)(C)CC(C)(C)C)C1=CC=CC=C1 IMXRBCGZTVENAC-UHFFFAOYSA-N 0.000 description 1
150000002790 naphthalenes Chemical class 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
WSPVKEAOQPRDDL-UHFFFAOYSA-N o-(2-methoxyethyl) carbamothioate Chemical compound COCCOC(N)=S WSPVKEAOQPRDDL-UHFFFAOYSA-N 0.000 description 1
ZWIPXAAUHSBJKM-UHFFFAOYSA-N o-(3-methylbutyl) carbamothioate Chemical compound CC(C)CCOC(N)=S ZWIPXAAUHSBJKM-UHFFFAOYSA-N 0.000 description 1
JPWQSSQOIDBJBI-UHFFFAOYSA-N o-benzyl carbamothioate Chemical compound NC(=S)OCC1=CC=CC=C1 JPWQSSQOIDBJBI-UHFFFAOYSA-N 0.000 description 1
QAJGLUWFOPZGOC-UHFFFAOYSA-N o-prop-2-enyl carbamothioate Chemical compound NC(=S)OCC=C QAJGLUWFOPZGOC-UHFFFAOYSA-N 0.000 description 1
XOOVLDXDHKQPCR-UHFFFAOYSA-N o-propan-2-yl carbamothioate Chemical compound CC(C)OC(N)=S XOOVLDXDHKQPCR-UHFFFAOYSA-N 0.000 description 1
125000004365 octenyl group Chemical group C(=CCCCCCC)* 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
RQMISGSERXWITM-UHFFFAOYSA-N octylcarbamothioic s-acid Chemical compound CCCCCCCCNC(S)=O RQMISGSERXWITM-UHFFFAOYSA-N 0.000 description 1
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 1
235000005985 organic acids Nutrition 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
150000002918 oxazolines Chemical class 0.000 description 1
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 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
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
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
125000002255 pentenyl 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
125000004344 phenylpropyl group Chemical group 0.000 description 1
229920001083 polybutene Polymers 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
230000000630 rising effect Effects 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 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
238000010561 standard procedure Methods 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
239000012258 stirred mixture Substances 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
239000010689 synthetic lubricating oil 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
150000007970 thio esters Chemical group 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
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
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
125000005023 xylyl group Chemical group 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 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
- C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
- C10M135/32—Heterocyclic sulfur, selenium or tellurium compounds
- C10M135/34—Heterocyclic sulfur, selenium or tellurium compounds the ring containing sulfur and carbon only
- 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
- C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
- 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
- C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
- C10M2219/102—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon only in the ring
- 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
- C10M2219/10—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
- 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
- C10M2219/10—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
- C10M2219/106—Thiadiazoles

Definitions

the present invention relates to the use of N, N-di-substituted S-thiiranylmethylcarbamothioates as lubricant additives and lubricant compositions containing them.
Additives are usually added to mineral and synthetic lubricants to improve their performance. Additives that protect the device to be lubricated from frictional wear are of particular importance. Such additives are required to increase the load-bearing capacity of the lubricant, not to have a corrosive effect on the metal parts to be lubricated and to have good heat resistance.
compounds containing phosphorus and sulfur are preferably used today, e.g. Dialkyldithiophosphate according to DE-A 2,921,620.
the phosphorus content of lubricating oils should be kept as low as possible so that the catalysts are not deactivated (H.S. Vogel et al., Applied Catalysis 3 (1982), 79-82).
N, N-disubstituted S-thiiranylmethylcarbamothioates and their use as herbicides are known, for example, from US Pat. No. 3,634,457.
the use of the compounds mentioned as lubricant additives has not yet been described.
N, N-disubstituted S-thiiranylmethylcarbamothioates in mineral and synthetic lubricants have excellent properties with regard to protection from frictional wear, laundering and ashlessness.
the invention therefore relates to compositions containing a lubricant and at least one compound of the formula I.
R 1 and R 2 independently of one another are C 1 -C 24 -alkyl, which can optionally be interrupted once or more by -0-, -S- or / and -N- and / or which optionally has one or more oxo- or / and can contain thiono groups, C 3 -C 24 alkenyl, C 2 -C 4 hydroxyalkyl, C 5 -C 8 cycloalkyl, or unsubstituted or with one or two C 1 -C 12 alkyl, C 1 -C 4 -Alkoxy-, C 2 -C 24 -alkoxycarbonyl or / and nitro groups substituted phenyl, naphthyl, C 7 -C 10 aralkyl, furan-2-yl-methyl or tetrahydrofuran-2-yl-methyl or R 1 and R 2 together with the
R 1 and R 2 are C 1 -C 24 -alkyl, they are straight-chain or branched substituents, for example methyl, ethyl, n-propyl, isopropyl, n-, sec- or tert-butyl, 1, 3-dimethylbutyl, 2-ethylbutyl, n-pentyl, isopentyl, 1-methylpentyl, n-hexyl, 2-ethylhexyl, n-heptyl, isoheptyl, 1-methylheptyl, n-octyl, straight-chain or branched nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, octadecyl or eicosyl.
Preferred is C I -C 20 -, especially C 1 -C 12
Alkyl substituents R 1 and R 2 which are represented by -0-, or / and -S-interrupted and / or substituted with oxo or / and thiono groups, preferably have 2-18, in particular 3-12, especially 3-7 C atoms. Particular mention should be made of alkoxyalkyl, alkoxyalkoxy, polyalkoxy (especially polyethoxy) alkyl, alkylthioalkyl, alkylaminoalkyl and dialkylaminoalkyl radicals.
the oxo or thiono groups can, for example, also sit on a carbon atom adjacent to a -0-, -N- or -S-chain link, which results in alkyl chains which are interrupted, for example, by ester, amide or thioester functions.
alkyl chains which are interrupted, for example, by ester, amide or thioester functions.
examples of such radicals are, for example, those of the formula -alkylene-C00-alkyl, -alkylene-CON-alkyl or -alkylene-C (S) 0-alkyl.
the chain length of alkylene + alkyl is as described above for the entire alkyl radical.
Preferred alkyl radicals with heteroatoms are those which, as shown above, contain ester or amide functions, but in particular alkoxyalkyl (for example with 3-7 C atoms), alkoxyalkoxyalkyl or polyethoxyalkyl, for example polyethoxyethyl.
alkyl radicals R 3 which may be mentioned are: methyl, ethyl, n-propyl, isopropyl, n-, sec- or tert-butyl, 1,3-dimethylbutyl, 2-ethylbutyl, n-pentyl, isopentyl, 1-methylpentyl, n-hexyl, 2-ethylhexyl, n-heptyl, isoheptyl, 1-methylheptyl, n-octyl.
R 3 is preferably hydrogen or C 1 -C 4 -alkyl.
R 1 and R 2 with the meaning C 2 -C 4 -hydroxyalkyl can be, for example, 2-hydroxyethyl, 2-hydroxypropyl, 3-hydroxypropyl, 2-hydroxybutyl or 4-hydroxybutyl, 2-hydroxyethyl being preferred.
R 1 and R 2 are, for example, allyl, butenyl, pentenyl or hexenyl, octenyl, decenyl, dodecenyl or oleyl. Preferred is C 3 -C 18 , especially C 3 -C 7 alkenyl, especially allyl. If R 1 and R 2 are C 3 -C 8 cycloalkyl, it is, for example, cyclopentyl, cyclohexyl, 4-methylcyclohexyl or cyclooctyl. Here R 1 and R 2 are preferably a C 5 -C 6 cycloalkyl radical and particularly preferably a cyclohexyl radical.
R 1 and R 2 as phenyl mono- or disubstituted with C 1 -C 12 alkyl or C 1 -C 4 alkoxy, C 2 -C 24 alkoxycarbonyl and / or nitro, for example 2-, 3- or 4-Tolyl, xylyl, 4-isopropylphenyl, 4-tert-butylphenyl, 3-methoxyphenyl or 4-propoxyphenyl, 3-carbethoxyphenyl or 3-nitrophenyl.
a phenyl radical is only substituted with one type of substituent.
An alkoxycarbonyl substituent preferably has 2-18, in particular 2-12, especially 2-5 C atoms.
R 1 and R 2 are preferably phenyl which is mono- or disubstituted by C 1 -C 4 -alkyl radicals.
R 1 and R 2 is a C 7 -C lo aralkyl radical may be, for example, benzyl, a-methylbenzyl, a, a-dimethylbenzyl, 1-phenylethyl, 2-phenylethyl, 2-phenylpropyl, 3- Act phenylpropyl or 3- (4-tolyl) propyl.
the meaning of benzyl for R 1 and R 2 is preferred.
R 1 and R 2 together with the N atom to which they are attached form a 5- or 6-membered aliphatic heterocyclic ring, they preferably contain no further hetero atom or an additional N or 0 atom as ring member or / and one or two oxo groups.
Preferred rings are the pyrrolidine, oxazolidine, piperidine, imidazolidine, morpholine, piperazine, 4-methylpiperazine or 4-ethylpiperazine residue, in particular the pyrrolidine, piperidine or horpholine residue.
R 1 and R 2 together with the N atom to which they are attached form an unsubstituted or mono-, disubstituted or trisubstituted by methyl groups indoline, 1,2,3,4-tetrahydroisoquinoline or 1,2,3, 4-tetrahydroquinoline ring, so it is preferably an unsubstituted 1,2,3,4-tetrahydroquinolinyl radical or a 2,2,4-trimethyl-1,2,3,4-tetrahydroquinolinyl radical.
lubricant compositions which contain at least one compound of the formula I in which R 1 and R 2 independently of one another are C 1 -C 20 -alkyl, C 3 -C 7 -alkenyl, C 2 -C 4 -hydroxyalkyl, C 3 - C 12 alkoxyalkyl, Cs-Ca cycloalkyl, phenyl, naphthyl, C 7 -C 9 aralkyl, unsubstituted or substituted with one or two C 1 -C 12 alkyl or C 1 -C 4 alkoxy radicals, furan 2-yl-methyl or tetrahydrofuran-2-yl-methyl or R 1 and R 2 together with the N atom to which they are attached are a 5- or 6-membered aliphatic heterocyclic ring or an indolinyl, 1 , 2,3,4-tetrahydroquinolinyl or 1,2,3,4-tetrahydroisoquinolinyl radical.
a subgroup of the compositions according to the invention contains, in addition to a lubricant, at least one compound of the formula I in which R 1 and R 2 are, independently of one another, C 1 -C 24 -alkyl, optionally once or more times by -0-, -S- or / and -N - Can be interrupted and / or which may optionally contain one or more oxo and / or thiono groups, C 3 -C 24 alkenyl, C 5 -C 8 cycloalkyl, unsubstituted or with one or two C 1 -C 12 alkyl -, C 1 -C 4 alkoxy, C 2 -C 24 alkoxycarbonyl or / and nitro groups substituted phenyl, naphthyl, C 7 -C 9 aralkyl, furan-2-yl-methyl or tetrahydrofuran-2-yl- are methyl and R 3 is hydrogen or C 1 -C 8 alkyl.
compositions according to the invention contains, in addition to a lubricant, at least one compound of the formula I in which R 1 and R 2 together with the N atom to which they are attached form a 5- or 6-membered mononuclear aliphatic-heterocyclic ring or a Form indolinyl, 1,2,3,4-tetrahydroquinolinyl or 1,2,3,4-tetrahydroisoquinolinyl areat.
compositions containing a lubricant and at least one compound of the formula I in which R 1 and R 2 independently of one another are C 1 -C 8 alkyl, cyclohexyl, phenyl or benzyl or R 1 and R 2 together with the N atom are particularly preferred to which they are attached represent a pyrrolidinyl, piperidinyl, morpholinyl or 1,2,3,4-tetrahydroquinolinyl radical.
compositions according to the invention contain a lubricant and at least one compound of the formula I in which R 1 is phenyl or benzyl and R 2 is C 1 -C 4 alkyl or benzyl or R 1 and R 2 together with the N atom to which they are attached form a piperidine or morpholine ring.
the compounds of the formula I are known and can be prepared, for example, in accordance with US Pat. No. 3,634,457, either by reacting dithiocarbamates of the formula wherein R 1 and R 2 have the meaning given, with epichlorohydrin or by reacting secondary amines of the formula wherein R 1 and R 2 have the meaning given, can be obtained with carbon disulfide and epichlorohydrin.
the N, N-disubstituted S-thiiranlymethylcarbamothioates provide lubricant additives which are characterized by good high-pressure and, in particular, wear protection properties. In addition, they do not have a corrosive effect on the metal parts to be lubricated.
the compounds of the formula I act in very small amounts in lubricants. Mineral and synthetic lubricating oils and mixtures thereof which have 0.05 to 5% by weight, based on the lubricant, and preferably 0.05 to 3% by weight of a compound of the formula I, have excellent properties, in particular wear protection properties.
the lubricants in question are familiar to the person skilled in the art, and e.g. in "Lubricants and related products" (Verlag Chemie, Weinheim, 1982).
the additives according to the invention are thermostable in mineral and synthetic lubricants; they are ash free and phoaphor free. The latter is particularly important with regard to the use of lubricants in internal combustion engines with catalyzers in the exhaust system, which age faster due to phoaphoorrüt masses.
the invention therefore also relates to the use of compounds of the formula I as additives to mineral and synthetic lubricants.
the lubricants can additionally contain other additives which are added in order to further improve the basic properties of lubricants; these include: antioxidants, metal passivators, rust inhibitors, viscosity index improvers, pour point depressants, dispersants, detergents, as well as other high-pressure additives and anti-wear additives.
metal passivators examples are:
rust inhibitors are:
Viakoaitktaindex verbeaaerer are e.g.
Polymethacrylates vinyl pyrrolidone / methacrylate copolymers, polybutenes, olefin copolymers, styrene / acrylate copolymers.
pour point depressors are, for example:
dispersing agents / tenaids examples include:
Polybutenylberateinic acid imides polybutenylphosphonic acid derivatives, basic magnesium, calcium and barium sulfates and phenolates.
Verachleisutzutz additive examples include:
Compounds containing sulfur and / or phosphorus and / or halogen such as hydrogenated vegetable oils, zinc dialkyldithiophoaphate, tritolyl-phoaphat, chlorinated paraffins, alkyl and aryldiaulfides.
the viscous oil is diluted with 100 ml of toluene and mixed with 14.0 ml (0.1 mol) of triethylamine.
Examples 3-11 Analogously to Example 1, further compounds are prepared, which are listed in Table 1.

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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)

EP86810334A 1985-07-30 1986-07-24 Additifs pour compositions lubrifiantes Expired - Lifetime EP0211806B1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH3291/85		1985-07-30
CH329185		1985-07-30

Publications (3)

Publication Number	Publication Date
EP0211806A2 true EP0211806A2 (fr)	1987-02-25
EP0211806A3 EP0211806A3 (en)	1988-06-08
EP0211806B1 EP0211806B1 (fr)	1990-01-24

Family

ID=4252803

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
EP86810334A Expired - Lifetime EP0211806B1 (fr)	1985-07-30	1986-07-24	Additifs pour compositions lubrifiantes

Country Status (5)

Country	Link
US (1)	US4734210A (fr)
EP (1)	EP0211806B1 (fr)
JP (1)	JPH0778231B2 (fr)
CA (1)	CA1277308C (fr)
DE (1)	DE3668465D1 (fr)

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US4965005A (en) *	1987-09-17	1990-10-23	Ciba-Geigy Corporation	Aminomethyl derivatives of monothiocarbamates and dithiocarbamates as additives for lubricants
US5405545A (en) *	1993-03-02	1995-04-11	Mobil Oil Corporation	Antiwear and antioxidant additives
DE102009010504B4 (de) *	2009-02-25	2012-03-29	Carl Zeiss Jena Gmbh	Immersionsflüssigkeit und Verfahren zur Herstellung einer organischen Verbindung für eine Immersionsflüssigkeit
US11345873B2 (en) *	2019-08-14	2022-05-31	Valvoline Licensing And Intellectual Property Llc	Lubricant composition containing ashless TBN molecules

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Publication number	Priority date	Publication date	Assignee	Title
US3561949A (en) *	1967-03-24	1971-02-09	Gulf Research Development Co	Herbicidal method using 2-chloro-3-mercaptopropyl n, n-substituted thiolcarbamates
US3634457A (en) *	1967-03-24	1972-01-11	Gulf Research Development Co	2 3-epithiopropyl n n-dialkyl-thiolcar-bamates and use as herbicid
US3809651A (en) *	1971-04-07	1974-05-07	Texaco Inc	Lubricating oil containing an alkylmercaptosuccinimide
JPS5234923A (en) *	1975-09-11	1977-03-17	Kao Corp	Novel antimicrobial agents for non-medical use
US4358597A (en) *	1976-09-20	1982-11-09	Standard Oil Company (Indiana)	Thiocarbamates of 1,3,4-thiadiazole-2,5-dithiol
US4225450A (en) *	1977-07-21	1980-09-30	Ciba-Geigy Corporation	Lubricant compositions containing dithiocarbamyl antioxidants
US4217233A (en) *	1977-08-31	1980-08-12	Ciba-Geigy Corporation	Epithio compounds as additives for lubricants
GB1569730A (en) *	1978-05-30	1980-06-18	Ciba Geigy Ag	0,0-diiso-propyl-s-(2-carboethoxyethyl)-phosphorodithioate and lubricating oil compositions containing it

1986
- 1986-07-22 US US06/888,910 patent/US4734210A/en not_active Expired - Lifetime
- 1986-07-24 DE DE8686810334T patent/DE3668465D1/de not_active Expired - Lifetime
- 1986-07-24 EP EP86810334A patent/EP0211806B1/fr not_active Expired - Lifetime
- 1986-07-28 CA CA000514740A patent/CA1277308C/fr not_active Expired - Lifetime
- 1986-07-30 JP JP61179780A patent/JPH0778231B2/ja not_active Expired - Lifetime

Also Published As

Publication number	Publication date
JPH0778231B2 (ja)	1995-08-23
CA1277308C (fr)	1990-12-04
JPS6232189A (ja)	1987-02-12
EP0211806B1 (fr)	1990-01-24
EP0211806A3 (en)	1988-06-08
DE3668465D1 (de)	1990-03-01
US4734210A (en)	1988-03-29

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Publication	Publication Date	Title
EP0233140B1 (fr)	1989-11-08	Additifs pour lubrifiants contenant du soufre et de l'azote
EP0376889B1 (fr)	1993-05-19	Composition lubrifiante
EP0267875B1 (fr)	1991-04-03	Composition lubrifiante pour haute température
EP0160620B1 (fr)	1989-09-13	Désactivateurs de métaux
EP0346283B1 (fr)	1992-07-29	Composition lubrifiante
EP0166696B1 (fr)	1989-07-19	Additifs pour lubrifiants
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DE3607884A1 (de)	1986-09-25	Stickstoffhaltige zusaetze fuer nicht-waessrige funktionelle fluessigkeiten
EP0205398B1 (fr)	1989-11-08	Additif pour fluides fonctionnels
EP0211806B1 (fr)	1990-01-24	Additifs pour compositions lubrifiantes
EP0317513A2 (fr)	1989-05-24	Dérivés de mercaptotriazines comme additifs pour lubrifiants
EP0220136B1 (fr)	1989-04-19	Complexes de l'acide borique
EP0307886B1 (fr)	1992-11-25	Dérivés amino-méthyles de mono- et dithiocarbamates comme additifs de lubrifiants
EP0524145A1 (fr)	1993-01-20	Additifs multifonctionnels pour lubrifiants
EP0157731A1 (fr)	1985-10-09	Additifs pour lubrifiants
EP0466639B1 (fr)	1994-08-10	Composition de lubrifiant
EP0480875B1 (fr)	1994-05-04	Composition de lubrifiant
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DE69007214T2 (de)	1994-07-14	Butenylaromatische Aminstabilisatoren.
EP0183642A1 (fr)	1986-06-04	Thioéthers contenant du bore comme additifs
EP0322362A1 (fr)	1989-06-28	Dérivés de thiadiazoles comme additifs pour lubrifiants
US4919832A (en)	1990-04-24	N-substituted tetrahydroquinolines for use as antioxidants in lubricants
EP0595770B1 (fr)	1998-01-14	Nouveaux dithiophosphates comme additifs anti-usure
EP0349483B1 (fr)	1994-02-09	Des additifs pour fluides fonctionnels