EP0267875A2 - Composition lubrifiante pour haute température - Google Patents

Composition lubrifiante pour haute température Download PDF

Info

Publication number: EP0267875A2
Authority: EP; European Patent Office
Prior art keywords: alkyl; hydrogen; composition according; formulas; compound
Prior art date: 1986-11-11
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

EP87810638A

Other languages

German (de)

English (en)

Other versions

EP0267875B1 (fr

EP0267875A3 (en

Inventor

Horst Dr. Zinke

Rolf Dr. Schumacher

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.)

1986-11-11

Filing date

1987-11-05

Publication date

1988-05-18

1987-11-05 Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG

1988-05-18 Publication of EP0267875A2 publication Critical patent/EP0267875A2/fr

1988-10-05 Publication of EP0267875A3 publication Critical patent/EP0267875A3/de

1991-04-03 Application granted granted Critical

1991-04-03 Publication of EP0267875B1 publication Critical patent/EP0267875B1/fr

2007-11-05 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

239000000314 lubricant Substances 0.000 title claims abstract description 24
239000000203 mixture Substances 0.000 claims abstract description 74
150000001875 compounds Chemical class 0.000 claims abstract description 62
239000010720 hydraulic oil Substances 0.000 claims abstract description 15
239000003921 oil Substances 0.000 claims abstract description 9
239000002480 mineral oil Substances 0.000 claims abstract description 4
235000010446 mineral oil Nutrition 0.000 claims abstract description 3
239000001257 hydrogen Substances 0.000 claims description 49
229910052739 hydrogen Inorganic materials 0.000 claims description 49
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 26
229910052717 sulfur Inorganic materials 0.000 claims description 25
239000011593 sulfur Substances 0.000 claims description 25
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
229910052760 oxygen Inorganic materials 0.000 claims description 23
239000001301 oxygen Substances 0.000 claims description 23
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 22
125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 20
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
150000002431 hydrogen Chemical group 0.000 claims description 18
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
239000000654 additive Substances 0.000 claims description 13
125000006686 (C1-C24) alkyl group Chemical group 0.000 claims description 10
125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 10
229910052751 metal Inorganic materials 0.000 claims description 8
239000002184 metal Substances 0.000 claims description 8
125000001624 naphthyl group Chemical group 0.000 claims description 8
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
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 6
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
150000001768 cations Chemical class 0.000 claims description 4
125000005842 heteroatom Chemical group 0.000 claims description 4
125000006528 (C2-C6) alkyl group Chemical group 0.000 claims description 3
125000003342 alkenyl group Chemical group 0.000 claims description 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
-1 phosphorus compound Chemical class 0.000 description 56
150000003254 radicals Chemical class 0.000 description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
150000001412 amines Chemical class 0.000 description 7
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
235000019198 oils Nutrition 0.000 description 7
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 6
125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
150000002148 esters Chemical class 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 6
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
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 6
229910052698 phosphorus Inorganic materials 0.000 description 6
239000011574 phosphorus Substances 0.000 description 6
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
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 5
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 5
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
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 5
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
125000002960 margaryl 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])[H] 0.000 description 4
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 4
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 4
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 4
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 4
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
125000001204 arachidyl 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])C([H])([H])C([H])([H])[H] 0.000 description 3
239000002199 base oil Substances 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
125000000755 henicosyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
150000002391 heterocyclic compounds Chemical class 0.000 description 3
125000000623 heterocyclic group Chemical group 0.000 description 3
239000003112 inhibitor Substances 0.000 description 3
238000000034 method Methods 0.000 description 3
125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
238000006467 substitution reaction Methods 0.000 description 3
239000011701 zinc Substances 0.000 description 3
229910052725 zinc Inorganic materials 0.000 description 3
125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 2
125000006701 (C1-C7) alkyl group Chemical group 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
ICKWICRCANNIBI-UHFFFAOYSA-N 2,4-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C(C(C)(C)C)=C1 ICKWICRCANNIBI-UHFFFAOYSA-N 0.000 description 2
LUZUXOXQSIDTMB-UHFFFAOYSA-N 2-amino-1,3-benzothiazole-4-thiol Chemical class C1=CC=C2SC(N)=NC2=C1S LUZUXOXQSIDTMB-UHFFFAOYSA-N 0.000 description 2
IKEHOXWJQXIQAG-UHFFFAOYSA-N 2-tert-butyl-4-methylphenol Chemical compound CC1=CC=C(O)C(C(C)(C)C)=C1 IKEHOXWJQXIQAG-UHFFFAOYSA-N 0.000 description 2
XOUQAVYLRNOXDO-UHFFFAOYSA-N 2-tert-butyl-5-methylphenol Chemical compound CC1=CC=C(C(C)(C)C)C(O)=C1 XOUQAVYLRNOXDO-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
WTZPWDHBSKBJLJ-UHFFFAOYSA-N OCC(C)(CO)C.OCC(CO)(CO)CO.C(CCCCCO)O.C(COCCOCCO)O.C(CCCCCCCCCCCCCCCCC)O.C(COCCO)O.CO Chemical compound OCC(C)(CO)C.OCC(CO)(CO)CO.C(CCCCCO)O.C(COCCOCCO)O.C(CCCCCCCCCCCCCCCCC)O.C(COCCO)O.CO WTZPWDHBSKBJLJ-UHFFFAOYSA-N 0.000 description 2
229910019142 PO4 Inorganic materials 0.000 description 2
229910000831 Steel Inorganic materials 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
150000003973 alkyl amines Chemical class 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
239000003963 antioxidant agent Substances 0.000 description 2
239000011575 calcium Substances 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
229920001577 copolymer Polymers 0.000 description 2
239000003599 detergent Substances 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
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
125000002463 lignoceryl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000010687 lubricating oil Substances 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
229910052757 nitrogen Inorganic materials 0.000 description 2
125000004433 nitrogen atom Chemical group N* 0.000 description 2
125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
235000021317 phosphate Nutrition 0.000 description 2
125000004437 phosphorous atom Chemical group 0.000 description 2
150000003018 phosphorus compounds Chemical class 0.000 description 2
229920013639 polyalphaolefin Polymers 0.000 description 2
229920000193 polymethacrylate Polymers 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
239000010959 steel Substances 0.000 description 2
150000005846 sugar alcohols Polymers 0.000 description 2
YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 2
HXORCSMYVPADFO-UHFFFAOYSA-N 1,1-bis(sulfanylidene)-1,3,4-thiadiazolidine-2,5-dithione Chemical class S=C1NNC(=S)S1(=S)=S HXORCSMYVPADFO-UHFFFAOYSA-N 0.000 description 1
HYZPNYHIWKHAAT-UHFFFAOYSA-N 1,1-bis(sulfanylidene)-1,3-benzothiazol-2-amine Chemical class C1=CC=C2S(=S)(=S)C(N)=NC2=C1 HYZPNYHIWKHAAT-UHFFFAOYSA-N 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
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
SKCLFSWRVSVQRL-UHFFFAOYSA-N 2,5-bis(2-methylbutan-2-yl)benzene-1,4-diol;2,5-ditert-butylbenzene-1,4-diol;2,6-ditert-butyl-4-methoxyphenol;4-octadecoxy-2,6-diphenylphenol Chemical compound CC(C)(C)C1=CC(O)=C(C(C)(C)C)C=C1O.COC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1.CCC(C)(C)C1=CC(O)=C(C(C)(C)CC)C=C1O.C=1C(OCCCCCCCCCCCCCCCCCC)=CC(C=2C=CC=CC=2)=C(O)C=1C1=CC=CC=C1 SKCLFSWRVSVQRL-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
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
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
BBWNYGQINDLVFV-UHFFFAOYSA-N 2-amino-3h-1,3-benzothiazole-2-thiol Chemical class C1=CC=C2SC(N)(S)NC2=C1 BBWNYGQINDLVFV-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
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
DHKGWJHJJZJZGD-UHFFFAOYSA-N 2-tert-butyl-4-(2-methylpropyl)phenol Chemical compound CC(C)CC1=CC=C(O)C(C(C)(C)C)=C1 DHKGWJHJJZJZGD-UHFFFAOYSA-N 0.000 description 1
LZHCVNIARUXHAL-UHFFFAOYSA-N 2-tert-butyl-4-ethylphenol Chemical compound CCC1=CC=C(O)C(C(C)(C)C)=C1 LZHCVNIARUXHAL-UHFFFAOYSA-N 0.000 description 1
BKZXZGWHTRCFPX-UHFFFAOYSA-N 2-tert-butyl-6-methylphenol Chemical compound CC1=CC=CC(C(C)(C)C)=C1O BKZXZGWHTRCFPX-UHFFFAOYSA-N 0.000 description 1
FLZYQMOKBVFXJS-UHFFFAOYSA-N 3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propanoic acid Chemical compound CC1=CC(CCC(O)=O)=CC(C(C)(C)C)=C1O FLZYQMOKBVFXJS-UHFFFAOYSA-N 0.000 description 1
WVRNUXJQQFPNMN-VAWYXSNFSA-N 3-[(e)-dodec-1-enyl]oxolane-2,5-dione Chemical compound CCCCCCCCCC\C=C\C1CC(=O)OC1=O WVRNUXJQQFPNMN-VAWYXSNFSA-N 0.000 description 1
125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
TXYNWJGERAWJTE-UHFFFAOYSA-N 4-[1,1-bis(sulfanylidene)-1,3-benzothiazol-2-yl]morpholine Chemical compound N=1C2=CC=CC=C2S(=S)(=S)C=1N1CCOCC1 TXYNWJGERAWJTE-UHFFFAOYSA-N 0.000 description 1
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ZEZSYLKJRJYGEQ-UHFFFAOYSA-N 4-n-octan-2-ylbenzene-1,4-diamine Chemical compound CCCCCCC(C)NC1=CC=C(N)C=C1 ZEZSYLKJRJYGEQ-UHFFFAOYSA-N 0.000 description 1
NTDQQZYCCIDJRK-UHFFFAOYSA-N 4-octylphenol Chemical compound CCCCCCCCC1=CC=C(O)C=C1 NTDQQZYCCIDJRK-UHFFFAOYSA-N 0.000 description 1
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TVMVHBGVTZJLLJ-UHFFFAOYSA-N C1(CCCCC1)NC1=CC=C(C=C1)NC1=CC=CC=C1.CC(CCCCCC)NC1=CC=C(C=C1)NC1=CC=CC=C1.CC(CC(C)C)NC1=CC=C(C=C1)NC1=CC=CC=C1.C(C)(C)NC1=CC=C(C=C1)NC1=CC=CC=C1 Chemical compound C1(CCCCC1)NC1=CC=C(C=C1)NC1=CC=CC=C1.CC(CCCCCC)NC1=CC=C(C=C1)NC1=CC=CC=C1.CC(CC(C)C)NC1=CC=C(C=C1)NC1=CC=CC=C1.C(C)(C)NC1=CC=C(C=C1)NC1=CC=CC=C1 TVMVHBGVTZJLLJ-UHFFFAOYSA-N 0.000 description 1
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FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
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230000015572 biosynthetic process Effects 0.000 description 1
BRJSYOUVIHAVLN-UHFFFAOYSA-L calcium 2,6-ditert-butyl-4-(dioctadecoxyphosphorylmethyl)phenol (3,5-ditert-butyl-4-hydroxyphenyl)methyl-ethoxyphosphinate Chemical compound [Ca++].CCOP([O-])(=O)Cc1cc(c(O)c(c1)C(C)(C)C)C(C)(C)C.CCOP([O-])(=O)Cc1cc(c(O)c(c1)C(C)(C)C)C(C)(C)C.CCCCCCCCCCCCCCCCCCOP(=O)(Cc1cc(c(O)c(c1)C(C)(C)C)C(C)(C)C)OCCCCCCCCCCCCCCCCCC BRJSYOUVIHAVLN-UHFFFAOYSA-L 0.000 description 1
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230000007797 corrosion Effects 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
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125000003493 decenyl group Chemical group [H]C([*])=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
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ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
NAGJZTKCGNOGPW-UHFFFAOYSA-N dithiophosphoric acid Chemical compound OP(O)(S)=S NAGJZTKCGNOGPW-UHFFFAOYSA-N 0.000 description 1
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NAQMVNRVTILPCV-UHFFFAOYSA-N hexamethylene diamine Natural products NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 1
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239000011777 magnesium Substances 0.000 description 1
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239000011707 mineral Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
ZYJKFKHANROOOP-UHFFFAOYSA-N n,n'-bis(2-methylphenyl)ethane-1,2-diamine;1-n,2-n-diphenylpropane-1,2-diamine Chemical compound C=1C=CC=CC=1NC(C)CNC1=CC=CC=C1.CC1=CC=CC=C1NCCNC1=CC=CC=C1C ZYJKFKHANROOOP-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
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125000006606 n-butoxy group Chemical group 0.000 description 1
CVVFFUKULYKOJR-UHFFFAOYSA-N n-phenyl-4-propan-2-yloxyaniline Chemical compound C1=CC(OC(C)C)=CC=C1NC1=CC=CC=C1 CVVFFUKULYKOJR-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
125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
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239000003208 petroleum Substances 0.000 description 1
150000004707 phenolate Chemical class 0.000 description 1
239000002530 phenolic antioxidant Substances 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
150000003014 phosphoric acid esters Chemical class 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
229920001515 polyalkylene glycol Polymers 0.000 description 1
229920001083 polybutene Polymers 0.000 description 1
229920000151 polyglycol Polymers 0.000 description 1
239000010695 polyglycol Substances 0.000 description 1
150000003141 primary amines Chemical group 0.000 description 1
125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
231100000241 scar Toxicity 0.000 description 1
239000000243 solution 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
150000003871 sulfonates Chemical class 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
230000002195 synergetic effect Effects 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
125000005063 tetradecenyl group Chemical group C(=CCCCCCCCCCCCC)* 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1
125000005040 tridecenyl group Chemical group C(=CCCCCCCCCCCC)* 0.000 description 1
XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Natural products NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 1
239000010723 turbine oil Substances 0.000 description 1
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235000015112 vegetable and seed oil Nutrition 0.000 description 1
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229920002554 vinyl polymer Polymers 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
- 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
- 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
- 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
- C10M135/36—Heterocyclic sulfur, selenium or tellurium compounds the ring containing sulfur and carbon with nitrogen or oxygen
- 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
- C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
- C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
- 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
- C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
- C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
- C10M137/04—Phosphate esters
- 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
- C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
- C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
- C10M137/04—Phosphate esters
- C10M137/06—Metal salts
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
- C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
- C10M137/04—Phosphate esters
- C10M137/08—Ammonium or amine salts
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
- C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
- C10M137/04—Phosphate esters
- C10M137/10—Thio derivatives
- 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
- C10M2219/09—Heterocyclic compounds containing no sulfur, selenium or tellurium compounds in the ring
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- C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
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- 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
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- 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
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- 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
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- 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
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- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
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- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
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- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
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- C10M2223/041—Triaryl phosphates
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- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
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- C10M2223/042—Metal salts thereof
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- 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
- C10M2223/04—Phosphate esters
- C10M2223/043—Ammonium or amine salts thereof
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- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
- C10M2223/045—Metal containing thio derivatives
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- 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
- C10M2223/04—Phosphate esters
- C10M2223/047—Thioderivatives not containing metallic elements
- 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
- 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
- C10M2223/10—Phosphatides, e.g. lecithin, cephalin
- 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
- C10N2010/00—Metal present as such or in compounds
- C10N2010/04—Groups 2 or 12
- 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 lubricant or hydraulic oil compositions containing, as additives, a mixture of an oil-soluble, optionally benzo-condensed 5-ring heterocycle with a tautomeric 2-mercapto-1,3-heteroatom-aza group and a phosphorus compound, and the use of these mixtures as Additives in lubricants or hydraulic oils.
Mineral and synthetic lubricants are usually added to improve their performance.
high-pressure and wear-reducing additives are added to the lubricants. These are required to have a non-corrosive effect on the metal parts to be lubricated and to have good heat resistance.
ZDTP zinc dialkyldithiophosphates
EP-A 150,957 also describes the use of mercaptobenzothiazole-amine salt solutions in excess amine to improve the antioxidative and anticorrosive properties of power transmission fluids. Furthermore, from US-A 3,779,919 rhodamine-amine salt are known as additives for improving the load-bearing capacity of synthetic turbine oils.
mixtures of oil-soluble 5-ring heterocycles which have a tautomeric 2-mercapto-1,3-heteroatom aza group and are optionally benzo-condensed, or their amine salts with various derivatives of phosphoric acid, thio- , Dithio- or trithiophosphoric acid esters and phosphorus acid esters have particularly good wear-reducing properties, in particular at higher temperatures, and at the same time have a reduced P content in the mixtures.
R1, R9, R11 and R12 are C1-C12-alkyl, it is straight-chain or branched alkyl radicals, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert. -Butyl, straight chain or branched pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl and dodecyl.
R10 and R16 C1-C17 alkyl it is straight-chain or branched alkyl radicals, such as methyl, ethyl, n-propyl, isopropyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl , straight-chain or branched pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl and heptadecyl.
alkyl radicals such as methyl, ethyl, n-propyl, isopropyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl , straight-chain or branched pentyl,
R5 and R8 C1-C22-alkyl it is straight-chain or branched alkyl radicals, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, straight-chain or branched pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, eicosyl, heneicosyl and docosyl.
alkyl radicals such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-buty
R2, R3 and R4 C1-C24-alkyl it is straight-chain or branched alkyl radicals, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl , straight-chain or branched pentyl, hexyl, heptyl, octyl, Nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, eicosyl, heneicosyl, docosyl tricosyl and tetracosyl.
alkyl radicals such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl
R13, R14 and R15 are C1-C30-alkyl, they are straight-chain or branched alkyl radicals, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec.-butyl, tert.- Butyl, straight chain or branched pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, eicosyl, heneicosyl, docosyl tricosyl, tetracosyl, pentacyl, pentacyl, pentacyl, pentacyl, pentacyl, pentacyl, pentacyl, pentacyl.
R2 and R13 represent hydroxy-substituted alkyl, it is mono- or polysubstituted hydroxy-substituted alkyl, with simple substitution the hydroxyl group preferably being terminal. In particular, it is 2-hydroxyethyl.
R11 and R12 represent C1-C12 alkyl which is interrupted by -O-, -S- or -C (O) O-, the hetero atom or the C (O) O group can be in any possible position are located, and the C1-C12-alkyl radical can be interrupted one or more times, the interruption can be done both by the same or different heteroatoms and by C (O) O groups. An interruption is preferred.
R10 and R16 are C2-C17 alkenyl and R3 and R4 C2-C24 alkenyl are straight-chain or branched alkenyl radicals which contain one or more, but preferably a double bond, such as vinyl, allyl, n-butenyl , 1,3-butadienyl, i-pentenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tridecenyl, 2-nonyl-2-butenyl, tetradecenyl, pentadecenyl, hexadecenyl and 8-heptadecenyl.
alkenyl radicals which contain one or more, but preferably a double bond, such as vinyl, allyl, n-butenyl , 1,3-butadienyl, i-penteny
R3 and R4 as alkenyl can also mean, for example, 2-octadecenyl, oleyl, nonadecenyl, eicosenyl, heneicosenyl, docosenyl, tricosenyl and tetracosenyl. 8-heptadecenyl and oleyl are preferred.
R1 as C1-C4 alkoxy can e.g. Be methoxy, ethoxy, isopropoxy or n-butoxy.
R1 as C2-C24 alkoxycarbonyl contains 1-24 carbon atoms in the alkyl part and can e.g. Methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl or 2-ethylhexyloxycarbonyl.
R11 and R12 represent phenyl or naphthyl substituted by C1-C12-alkyl, the phenyl or naphthyl radical can be substituted one or more times, but preferably one to two times;
C1-C12-alkyl is, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, straight-chain or branched nonyl or dodecyl.
R11 and R12 represent C5-C12-cycloalkyl, for example cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cycloundecyl or cyclododecyl, preferably cyclohexyl.
R11 and R12 represent C5-C12-cycloalkyl substituted by C1-C4-alkyl, it can be a single or multiple substitution, but is preferably a simple substitution; such as methylcyclohexyl, trimethylcyclohexyl, butylcyclohexyl or propylcyclopentyl.
R11 and R12 are C7-C13 aralkyl, for example benzyl, 1- or 2-phenethyl, 3-phenylpropyl, ⁇ , ⁇ -dimethylbenzyl, 2-phenylisopropyl, 2-phenylhexyl, benzhydryl or naphthylmethyl, but preferably around benzyl.
M is a k-valent metal cation
k in the case of k equals 1, it is, for example, Li ⁇ , Na ⁇ , K ⁇ and, in the case of k equals 2, it is, for example, Mg2 ⁇ , Ca2 ⁇ , Ba2 ⁇ , Zn2 ⁇ .
the preferred metal cation M is Zn2 ⁇ .
A preferably represents the values 0 or 1 to 1.25, but particularly preferably 0 or 1.2.
compositions are preferred in which in the compounds of the formulas I or II Y is oxygen or sulfur, but in particular sulfur.
compositions are further preferred in which, in the compounds of the formula I, R 1 is hydrogen and Y is sulfur.
compositions in which Z in the compounds of the formula II denotes -CR8-.
compositions in which in the compounds of the formulas I or II R2 is hydrogen or unsubstituted or -OH-substituted C1-C4alkyl, in particular hydrogen or methyl; further those in which in the compounds of the formulas I or II R3 is hydrogen, C8-C24-alkyl or C8-C24-alkenyl; or in the compounds of the formulas I or II R4 is C8-C24-alkyl or C8-C24-alkenyl.
compositions are particularly interesting in which, in the compounds of the formulas I or II, R2 is hydrogen and R3 and R4 are, independently of one another, C8-C24-alkyl or C8-C24-alkenyl; further those in which in the compounds of the formulas I or II R2 and R3 are methyl and R4 are C8-C24-alkyl or C8-C24-alkenyl; or such wherein in the compounds of formulas I or II R2 and R3 are hydrogen and R4 C4-C24-alkyl or C8-C24-alkenyl.
the radicals R3 and R4 as C8-C24-alkyl are preferably branched C8-C24-alkyl radicals, in particular those which contain tert.-C atoms, and particularly preferably those with a tert.-C atom in the ⁇ position to the N atom to which they are attached. If, for example, NR2R3R4 is a primary amine, preference is given to using mixtures of such amines as are commercially available under the name "Primene”.
the mixture “Primene®81-R” (mainly branched alkylamines with 12 to 15 C atoms) or the mixture “Primene®JM-T” (mainly branched alkylamines with 18 to 24 C atoms) can be used.
compositions in which in the compounds of the formulas I or II R2 is 2-hydroxyethyl and R3 together with R4 are a radical -C (R10) N-CH2CH2-, where R10 is hydrogen, C1-C17-alkyl or C2-C17 -Alkenyl, but preferably C8-C17-alkyl or C8-C17-alkenyl.
a further embodiment are compositions in which in the compounds of the formulas III or IV R11 is C1-C12-alkyl, which is optionally interrupted by -O-, -S- or -C (O) O-, or unsubstituted or by C1 -C12-alkyl, especially C8-C12-alkyl, substituted phenyl or naphthyl; Cyclohexyl or benzyl, where R11 is preferably C3-C12 alkyl, which is optionally interrupted by -C (O) O-, or phenyl or nonylphenyl.
compositions in which in the compounds of the formulas III or IV X is oxygen furthermore those in which in the compounds of the formulas III or IV X1 and X2 are oxygen or those in which in the compounds of the formulas III or IV X and X2 is sulfur and X1 is oxygen.
compositions in which X in the compounds of formulas III or IV is sulfur furthermore those in which in the compounds of formulas III or IV X is sulfur and X 1 and X 2 are oxygen; or those in which, in the compounds of the formulas III or IV, X is oxygen and X1 and X2 are sulfur.
compositions in which in the compounds of the formula III, R13 2-hydroxyethyl and R14 together with R15 represent a radical -C (R16) N-CH2-CH2-, where R16 is preferably C8-C17-alkyl or C8-C17 -Alkenyl means.
compositions are preferred in which the mixture b) consists of 1) a compound of the formulas I or II and 2) a compound of the formula III.
compositions in which mixture b) consists of 1) a compound of the formula I and 2) a compound of the formula III are very particularly preferred.
compositions are particularly preferred in which in the compounds of the formula I a has the value 1 to 1.25, Y is sulfur, R1 is hydrogen, R2 is hydrogen, R3 is hydrogen or C8-C24-alkyl and R4 C8-C24-alkyl and are in the Compounds of the formula III X and X2 sulfur, X1 oxygen, R11 C3-C8-alkyl, n * the number 2, m the number 1 and M Zn2+.
the components of the mixtures b) which can be used according to the invention are known.
the heterocyclic compounds are commercially available or can be easily prepared from commercially available products by generally known methods of organic chemistry. Your amine salts are obtained in the usual way by adding the corresponding amine (salt formation). The amine can also be used in excess (a> 1).
the preparation of the phosphorus compounds is described, for example, in Houben-Weyl, "Methods of Organic Chemistry", Volume 12, Part 2, 4th edition, G. Thieme Verlag, Stuttgart 1964, on pages 53-77, 143-210, 226-274, 299-376 and 587-748. Their amine salts are prepared analogously to those of the heterocyclic compounds.
Mixtures b) are prepared by methods known per se, for example by simple mixing.
2-mercaptobenzothiazole can be incorporated into a commercially available amine phosphate (phosphoric acid mono- / diester amine salts).
Mixtures b) are liquid, but of different viscosity. They are excellent as excellent wear protection additives for lubricants and hydraulic oils, preferably for lubricants. The mixtures according to the invention are particularly effective at high temperatures.
the present invention therefore furthermore relates to the use of mixtures of 1) at least one compound of the formulas I or II and 2) at least one compound of the formulas III or IV as wear-reducing additives to lubricants or hydraulic oils.
Mixtures b) are sufficiently soluble in lubricants and hydraulic oils and are in a concentration of 0.05 to 5% by weight, preferably in a concentration of 0.1 to 3% by weight, based on the total weight of the lubricants - or hydraulic oil composition used.
the ratio of 1): 2) is e.g. from 10: 1 to 1:10, preferably from 5: 1 to 1:10, particularly preferably from 2: 1 to 1: 5, in particular from 1: 1 to 1: 3.
the mixtures can be added to the lubricant as such, or the components such as 2-mercaptobenzothiazole-amine salts and the phosphorus compound can be prepared separately and the Lubricants are added separately in the formulation.
dilution with an appropriate base oil offers a favorable form of assembly.
mineral oils e.g. Poly- ⁇ -olefins, ester-based lubricants, phosphate esters, glycols, polyglycols and polyalkylene glycols.
the lubricants can additionally contain other additives which are added in order to further improve the basic properties of lubricants and hydraulic oils; these include antioxidants, metal passivators, rust inhibitors, viscosity index improvers, pour point depressants, dispersants, detergents, high-pressure additives and other wear protection additives.
N N ⁇ -di-isopropyl-p-phenylenediamine N, N ⁇ -di-sec-butyl-p-phenylenediamine N, N ⁇ -bis (1,4-dimethyl-pentyl) -p-phenylenediamine N, N ⁇ -bis (1-ethyl-3-methyl-pentyl) -p-phenylenediamine N, N ⁇ -bis (1-methyl-heptyl) -p-phenylenediamine N, N ⁇ -diphenyl-p-phenylenediamine N, N ⁇ -di- (naphthyl-2) -p-phenylenediamine N-isopropyl-N ⁇ -phenyl-p-phenylenediamine N- (1,3-dimethyl-butyl) -N ⁇ -phenyl-p-phenylenediamine N- (1-methyl-heptyl) -N ⁇ -phenyl-p-phenylened
metal passivators examples are:
Triazole for copper, for example: Triazole, benzotriazole and their derivatives, salicylidene-propylenediamine Salts of salicylaminoguanidine.
rust inhibitors are:
viscosity index improvers examples are:
Polymethacrylates vinyl pyrrolidone / methacrylate copolymers, polybutenes, olefin copolymers, styrene / acrylate copolymers.
pour point depressants examples 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 phosphates, chlorinated paraffins, alkyl and aryl disulfides.
the amine salts listed in Table 1 below are obtained by combining the corresponding molar proportions of the heterocyclic mercapto compound with an amine.
the mixtures indicated in Table 3 are prepared by adding compounds from Table 1 to phosphorus compounds.
the wear protection effect is determined using a commercial vibratory friction wear device (SRV device) from Optimol GmbH, Kunststoff. (R. Schumacher et al. ASLE Transaction 26 , 1 (1983), 94-101).
This device is based on the following principle: A steel ball (100 Cr 6), on which a force F N acts, oscillates on a steel cylinder.
the ball is fixed in a holder and therefore carries out an oscillating sliding movement.
the horizontal and vertical force is determined by a piezoelectric force transducer.
the maximum Herz normal stress is 2740 N / mm2
the maximum shear stress is 850 N / mm2.
Ball and cylinder are made from the same tool steel.
the following test conditions are chosen: Load: 200 N, frequency: 50 Hz, amplitude: 1000 ⁇ , Temperature: 130 ° C-150 ° C, test time: 2 h.
Test oil Polyalphaolefin ISO VG 100, S content ⁇ 1.5 ppm.
a cross section is recorded with a stylus (Talysurf from Rank Taylor Hobson, Leicester, England).
the integrated cross profile surface serves as a measure of wear.
the specified values are a relative measure of wear.
Test oil I Paraffin-based base oil ISO VG 32 with commercially available additives 0.75% zinc dialkyldithiophosphate (ZDTP) 11% detergent 6% viscosity index improver
Test oil II Test oil I + 0.5% Example 3 Test oil II thus contains mixture 34 as example 34

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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)

EP87810638A 1986-11-11 1987-11-05 Composition lubrifiante pour haute température Expired - Lifetime EP0267875B1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH4497/86		1986-11-11
CH449786		1986-11-11

Publications (3)

Publication Number	Publication Date
EP0267875A2 true EP0267875A2 (fr)	1988-05-18
EP0267875A3 EP0267875A3 (en)	1988-10-05
EP0267875B1 EP0267875B1 (fr)	1991-04-03

Family

ID=4277209

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
EP87810638A Expired - Lifetime EP0267875B1 (fr)	1986-11-11	1987-11-05	Composition lubrifiante pour haute température

Country Status (4)

Country	Link
US (1)	US4917809A (fr)
EP (1)	EP0267875B1 (fr)
JP (1)	JP2739576B2 (fr)
DE (1)	DE3769086D1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0368803A1 (fr) *	1988-11-08	1990-05-16	Ciba-Geigy Ag	Composition lubrifiante
EP0369804A1 (fr) *	1988-11-18	1990-05-23	Castrol Limited	Méthode de lubrification et compositions pour l'effectuer
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US6734149B2 (en)	2001-01-24	2004-05-11	Rohm And Haas Company	Combination of additives for lubricating oils
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EP1394242A3 (fr) *	2002-08-07	2004-04-21	Rohm And Haas Company	Thiourées cycliques et leur utilisation en tant qu'additifs pour huiles lubrifiantes
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1987
- 1987-11-02 US US07/115,287 patent/US4917809A/en not_active Expired - Fee Related
- 1987-11-05 DE DE8787810638T patent/DE3769086D1/de not_active Expired - Lifetime
- 1987-11-05 EP EP87810638A patent/EP0267875B1/fr not_active Expired - Lifetime
- 1987-11-11 JP JP62285139A patent/JP2739576B2/ja not_active Expired - Lifetime

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0368803A1 (fr) *	1988-11-08	1990-05-16	Ciba-Geigy Ag	Composition lubrifiante
EP0369804A1 (fr) *	1988-11-18	1990-05-23	Castrol Limited	Méthode de lubrification et compositions pour l'effectuer
WO1990005767A1 (fr) *	1988-11-18	1990-05-31	Castrol Limited	Procede et compositions de lubrification
EP0432089A1 (fr) *	1989-11-08	1991-06-12	Ciba-Geigy Ag	Compositions lubrifiantes

Also Published As

Publication number	Publication date
US4917809A (en)	1990-04-17
EP0267875B1 (fr)	1991-04-03
EP0267875A3 (en)	1988-10-05
JP2739576B2 (ja)	1998-04-15
DE3769086D1 (de)	1991-05-08
JPS63135495A (ja)	1988-06-07

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Publication	Publication Date	Title
EP0267875B1 (fr)	1991-04-03	Composition lubrifiante pour haute température
EP0233140B1 (fr)	1989-11-08	Additifs pour lubrifiants contenant du soufre et de l'azote
DE3446630C2 (de)	1995-08-10	Stabilisator-Systeme, deren Verwendung und diese enthaltende Schmierstoffe
EP0160620B1 (fr)	1989-09-13	Désactivateurs de métaux
EP0376889B1 (fr)	1993-05-19	Composition lubrifiante
EP0166696B1 (fr)	1989-07-19	Additifs pour lubrifiants
DE2601719C2 (fr)	1988-01-07
DE68903468T2 (de)	1993-04-15	Schmiermittelzusammensetzungen.
EP0273868B1 (fr)	1992-07-08	Tétrahydroquinoléines N-substituées comme anti-oxydants pour lubrifiants
DE3607884A1 (de)	1986-09-25	Stickstoffhaltige zusaetze fuer nicht-waessrige funktionelle fluessigkeiten
DE69000815T2 (de)	1993-07-22	Schmiermittelzusammensetzungen.
DE2814256A1 (de)	1978-10-12	Schmieroelzusatzstoffe
EP0214434A2 (fr)	1987-03-18	Substance lubrifiante en forme de poudre jusqu'à la forme pâteuse
EP0205398B1 (fr)	1989-11-08	Additif pour fluides fonctionnels
EP0303569A2 (fr)	1989-02-15	1,4-Oxathianones et 1,4-oxathiepanones et leur utilisation comme additifs pour liquides fonctionnels
DE60221381T2 (de)	2008-04-17	Alkyl hydrazid als zusätze für schmiermittel
EP0157731B1 (fr)	1988-10-12	Additifs pour lubrifiants
EP0524145B1 (fr)	1999-01-27	Additifs multifonctionnels pour lubrifiants
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
EP0211806B1 (fr)	1990-01-24	Additifs pour compositions lubrifiantes
EP0466639B1 (fr)	1994-08-10	Composition de lubrifiant
EP0322362B1 (fr)	1991-05-08	Dérivés de thiadiazoles comme additifs pour lubrifiants
EP0480875B1 (fr)	1994-05-04	Composition de lubrifiant