EP0432089A1 - Compositions lubrifiantes - Google Patents
Compositions lubrifiantes Download PDFInfo
- Publication number
- EP0432089A1 EP0432089A1 EP90810831A EP90810831A EP0432089A1 EP 0432089 A1 EP0432089 A1 EP 0432089A1 EP 90810831 A EP90810831 A EP 90810831A EP 90810831 A EP90810831 A EP 90810831A EP 0432089 A1 EP0432089 A1 EP 0432089A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- alkyl
- tert
- bis
- phenyl
- compounds
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 108
- 239000010687 lubricating oil Substances 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 103
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims abstract description 71
- 239000000314 lubricant Substances 0.000 claims abstract description 44
- 150000001412 amines Chemical class 0.000 claims abstract description 22
- OFLNOEMLSXBOFY-UHFFFAOYSA-K trisodium;dioxido-sulfanylidene-sulfido-$l^{5}-phosphane Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([S-])=S OFLNOEMLSXBOFY-UHFFFAOYSA-K 0.000 claims abstract description 12
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 11
- 150000004982 aromatic amines Chemical class 0.000 claims abstract description 8
- 150000002989 phenols Chemical class 0.000 claims abstract description 7
- -1 alkali metal cation Chemical class 0.000 claims description 163
- 125000000217 alkyl group Chemical group 0.000 claims description 106
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 65
- 229910052739 hydrogen Inorganic materials 0.000 claims description 60
- 125000004432 carbon atom Chemical group C* 0.000 claims description 57
- 239000001257 hydrogen Substances 0.000 claims description 41
- 229910052760 oxygen Inorganic materials 0.000 claims description 37
- 229910052757 nitrogen Inorganic materials 0.000 claims description 33
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 32
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 24
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
- 229910052799 carbon Inorganic materials 0.000 claims description 18
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 15
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 15
- 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 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- 239000011593 sulfur Substances 0.000 claims description 14
- 125000001931 aliphatic group Chemical group 0.000 claims description 13
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 13
- 239000001301 oxygen Substances 0.000 claims description 12
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
- GQBHYWDCHSZDQU-UHFFFAOYSA-N 4-(2,4,4-trimethylpentan-2-yl)-n-[4-(2,4,4-trimethylpentan-2-yl)phenyl]aniline Chemical compound C1=CC(C(C)(C)CC(C)(C)C)=CC=C1NC1=CC=C(C(C)(C)CC(C)(C)C)C=C1 GQBHYWDCHSZDQU-UHFFFAOYSA-N 0.000 claims description 10
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 10
- 125000002947 alkylene group Chemical group 0.000 claims description 10
- 239000011734 sodium Substances 0.000 claims description 9
- 239000003963 antioxidant agent Substances 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 7
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 7
- GXGJIOMUZAGVEH-UHFFFAOYSA-N Chamazulene Chemical group CCC1=CC=C(C)C2=CC=C(C)C2=C1 GXGJIOMUZAGVEH-UHFFFAOYSA-N 0.000 claims description 6
- 125000005394 methallyl group Chemical group 0.000 claims description 6
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- GNBVPFITFYNRCN-UHFFFAOYSA-M sodium thioglycolate Chemical compound [Na+].[O-]C(=O)CS GNBVPFITFYNRCN-UHFFFAOYSA-M 0.000 claims description 5
- 229940046307 sodium thioglycolate Drugs 0.000 claims description 5
- OPEKHRGERHDLRK-UHFFFAOYSA-N 4-tert-butyl-n-(4-tert-butylphenyl)aniline Chemical compound C1=CC(C(C)(C)C)=CC=C1NC1=CC=C(C(C)(C)C)C=C1 OPEKHRGERHDLRK-UHFFFAOYSA-N 0.000 claims description 4
- UOMXLEWVJZEVGP-UHFFFAOYSA-N 4-tert-butyl-n-phenylaniline Chemical compound C1=CC(C(C)(C)C)=CC=C1NC1=CC=CC=C1 UOMXLEWVJZEVGP-UHFFFAOYSA-N 0.000 claims description 4
- OSFOTMWFXQGWKZ-UHFFFAOYSA-N n-phenyl-4-(2,4,4-trimethylpentan-2-yl)aniline Chemical compound C1=CC(C(C)(C)CC(C)(C)C)=CC=C1NC1=CC=CC=C1 OSFOTMWFXQGWKZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000004437 phosphorous atom Chemical group 0.000 claims description 4
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical group FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 4
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims description 3
- RQVGZVZFVNMBGS-UHFFFAOYSA-N n-octyl-n-phenylaniline Chemical compound C=1C=CC=CC=1N(CCCCCCCC)C1=CC=CC=C1 RQVGZVZFVNMBGS-UHFFFAOYSA-N 0.000 claims description 3
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims description 3
- WPMYUUITDBHVQZ-UHFFFAOYSA-M 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=CC(CCC([O-])=O)=CC(C(C)(C)C)=C1O WPMYUUITDBHVQZ-UHFFFAOYSA-M 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 5
- 238000010525 oxidative degradation reaction Methods 0.000 abstract description 3
- HYTYHTSMCRDHIM-UHFFFAOYSA-M potassium;2-sulfanylacetate Chemical compound [K+].[O-]C(=O)CS HYTYHTSMCRDHIM-UHFFFAOYSA-M 0.000 abstract description 3
- 125000002015 acyclic group Chemical group 0.000 abstract 1
- 150000002990 phenothiazines Chemical class 0.000 abstract 1
- 239000003921 oil Substances 0.000 description 20
- 235000019198 oils Nutrition 0.000 description 20
- 150000003254 radicals Chemical class 0.000 description 19
- 239000002253 acid Substances 0.000 description 18
- 239000000654 additive Substances 0.000 description 15
- 150000002148 esters Chemical class 0.000 description 14
- FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical group CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
- 125000003118 aryl group Chemical group 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 125000001424 substituent group Chemical group 0.000 description 10
- 239000002480 mineral oil Substances 0.000 description 8
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 8
- 125000001589 carboacyl group Chemical group 0.000 description 7
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 125000003055 glycidyl group Chemical group C(C1CO1)* 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
- 239000011701 zinc Substances 0.000 description 6
- 229910052725 zinc Inorganic materials 0.000 description 6
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 5
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 5
- 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 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 5
- JWUXJYZVKZKLTJ-UHFFFAOYSA-N Triacetonamine Chemical compound CC1(C)CC(=O)CC(C)(C)N1 JWUXJYZVKZKLTJ-UHFFFAOYSA-N 0.000 description 5
- 230000000996 additive effect Effects 0.000 description 5
- XITRBUPOXXBIJN-UHFFFAOYSA-N bis(2,2,6,6-tetramethylpiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)NC(C)(C)C1 XITRBUPOXXBIJN-UHFFFAOYSA-N 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 235000010446 mineral oil Nutrition 0.000 description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 229910052698 phosphorus Inorganic materials 0.000 description 5
- 239000011574 phosphorus Substances 0.000 description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 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
- 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 5
- 230000035882 stress Effects 0.000 description 5
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 5
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 4
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
- 230000029936 alkylation Effects 0.000 description 4
- 238000005804 alkylation reaction Methods 0.000 description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 4
- 238000002485 combustion reaction Methods 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 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 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 4
- 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 4
- 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 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000011591 potassium Substances 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- 239000010802 sludge Substances 0.000 description 4
- 125000006686 (C1-C24) alkyl group Chemical group 0.000 description 3
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidine Chemical compound CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 3
- 125000004825 2,2-dimethylpropylene group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[*:1])C([H])([H])[*:2] 0.000 description 3
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 3
- 125000006024 2-pentenyl group Chemical group 0.000 description 3
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 3
- WPMYUUITDBHVQZ-UHFFFAOYSA-N 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoic acid Chemical group CC(C)(C)C1=CC(CCC(O)=O)=CC(C(C)(C)C)=C1O WPMYUUITDBHVQZ-UHFFFAOYSA-N 0.000 description 3
- SVMHJGGEHKZZCC-UHFFFAOYSA-N C(C)(C)(C)C=1C(=C(C=CC1)NC1=CC=CC=C1)C(C)(C)C Chemical compound C(C)(C)(C)C=1C(=C(C=CC1)NC1=CC=CC=C1)C(C)(C)C SVMHJGGEHKZZCC-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- GVETWXKNKJJNST-UHFFFAOYSA-N N-phenyl-2,3-bis(2,4,4-trimethylpentan-2-yl)aniline Chemical class CC(CC(C)(C)C)(C)C=1C(=C(C=CC1)NC1=CC=CC=C1)C(CC(C)(C)C)(C)C GVETWXKNKJJNST-UHFFFAOYSA-N 0.000 description 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 125000000732 arylene group Chemical group 0.000 description 3
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 125000002993 cycloalkylene group Chemical group 0.000 description 3
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 125000006547 cyclononyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 3
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 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 3
- 239000003599 detergent Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 229910001385 heavy metal Inorganic materials 0.000 description 3
- 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 3
- 239000003112 inhibitor Substances 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000006078 metal deactivator Substances 0.000 description 3
- 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 3
- MHJCZOMOUCUAOI-UHFFFAOYSA-N n-tert-butyl-n-phenylaniline Chemical compound C=1C=CC=CC=1N(C(C)(C)C)C1=CC=CC=C1 MHJCZOMOUCUAOI-UHFFFAOYSA-N 0.000 description 3
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 3
- 125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 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 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 3
- 229950000688 phenothiazine Drugs 0.000 description 3
- 229920000193 polymethacrylate Polymers 0.000 description 3
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- OLRJXMHANKMLTD-UHFFFAOYSA-N silyl Chemical compound [SiH3] OLRJXMHANKMLTD-UHFFFAOYSA-N 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 230000006641 stabilisation Effects 0.000 description 3
- 238000011105 stabilization Methods 0.000 description 3
- 150000005846 sugar alcohols Polymers 0.000 description 3
- 238000003878 thermal aging Methods 0.000 description 3
- NWPIOULNZLJZHU-UHFFFAOYSA-N (1,2,2,6,6-pentamethylpiperidin-4-yl) 2-methylprop-2-enoate Chemical compound CN1C(C)(C)CC(OC(=O)C(C)=C)CC1(C)C NWPIOULNZLJZHU-UHFFFAOYSA-N 0.000 description 2
- RSGJNCQIUIMQNW-UHFFFAOYSA-N (1-ethyl-2,2,6,6-tetramethylpiperidin-4-yl) 2-hydroxybenzoate Chemical compound C1C(C)(C)N(CC)C(C)(C)CC1OC(=O)C1=CC=CC=C1O RSGJNCQIUIMQNW-UHFFFAOYSA-N 0.000 description 2
- JMUOXOJMXILBTE-UHFFFAOYSA-N (2,2,6,6-tetramethylpiperidin-4-yl) octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC1CC(C)(C)NC(C)(C)C1 JMUOXOJMXILBTE-UHFFFAOYSA-N 0.000 description 2
- QGWZSQSEJMBWAF-UHFFFAOYSA-N (9-acetyl-3-ethyl-8,8,10,10-tetramethyl-1,5-dioxa-9-azaspiro[5.5]undecan-3-yl)methyl acetate Chemical compound O1CC(CC)(COC(C)=O)COC11CC(C)(C)N(C(C)=O)C(C)(C)C1 QGWZSQSEJMBWAF-UHFFFAOYSA-N 0.000 description 2
- NWHNXXMYEICZAT-UHFFFAOYSA-N 1,2,2,6,6-pentamethylpiperidin-4-ol Chemical compound CN1C(C)(C)CC(O)CC1(C)C NWHNXXMYEICZAT-UHFFFAOYSA-N 0.000 description 2
- GHJUORCGZFHNKG-UHFFFAOYSA-N 1,2,2,6,6-pentamethylpiperidin-4-one Chemical compound CN1C(C)(C)CC(=O)CC1(C)C GHJUORCGZFHNKG-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
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- MCYXWOCTIYEQRK-UHFFFAOYSA-K tripotassium dioxido-sulfanylidene-sulfido-lambda5-phosphane Chemical compound [K+].[K+].[K+].[O-]P([O-])([S-])=S MCYXWOCTIYEQRK-UHFFFAOYSA-K 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 150000007934 α,β-unsaturated carboxylic acids Chemical class 0.000 description 1
Classifications
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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
-
- 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
- C10M2223/04—Phosphate esters
- C10M2223/041—Triaryl phosphates
-
- 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
- C10M2223/04—Phosphate esters
- C10M2223/042—Metal salts thereof
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- 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
-
- 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
- C10N2010/02—Groups 1 or 11
Definitions
- Mineral lubricating oil mixtures and in particular steam turbine oils with improved stability are known for example from DE-AS 1 594 405.
- Steam turbine oils are described which contain an aliphatic carboxylic acid having at least 12 carbon atoms, an alkylphenol, an aromatic amine and a dialkyldithiophosphate.
- the alkali metal salts of dialkylthiophosphates are mentioned, preferred and only the zinc dialkyldithiophosphates have found their way into the practical examples.
- R X , M ⁇ , X, X 1 , X 2 , a and b in compounds of the general formula I have the following meanings, for example.
- R x represents C 7 -C 13 aralkyl which is interrupted in the alkyl radical by -0- or -S-, a typical example of this is a phenoxyethyl group.
- compositions in which in the compounds of formula IX is sulfur furthermore those in which in the compounds of formula IX are sulfur and X 1 and X 2 are oxygen; or those in which in the compounds of the formula IX are sulfur, X 1 is oxygen and X 2 is sulfur.
- R 1 and R 9 as cycloalkyl having 5 to 12 carbon atoms represent, for example, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cycloundecyl or cyclododecyl. Cyclohexyl is preferred.
- R "or R 12 can represent, for example, the groups mentioned above and, for example, n-tridecyl, n-tetradecyl, n-hexadecyl or n-octadecyl.
- R 12 represents a trivalent carboxylic acid residue, it means, for example, a trimellitic acid, citric acid or nitrilotriacetic acid residue.
- Any C 2 -C 12 alkylene substituents are, for example, ethylene, propylene, 2,2-dimethylpropylene, tetramethylene, hexamethylene, octamethylene, decamethylene or dodecamethylene.
- R 15 is C 2 -C 8 -alkylene or -hydroxyalkylene, it is, for example, ethylene, 1-methyl-ethylene, propylene, 2-ethyl-propylene or 2-ethyl-2-hydroxymethylpropylene.
- R 17 is C 2 -C 12 alkylene, it is, for example, ethylene, propylene, 2,2-dimethylpropylene, tetramethylene, hexamethylene, octamethylene, decamethylene or dodecamethylene.
- oligomers or polymeric compounds whose recurring structural unit contains a 2,2,6,6-tetraalkylpiperidine radical of the formula (VI), in particular polyesters, polyethers, polyamides, polyamines, polyurethanes, polyureas, polyaminotriazines, poly (meth) acrylates, poly ( meth) acrylamides and their copolymers which contain such radicals.
- 2,2,6,6-polyalkylpiperidine light stabilizers of this class are the compounds of the following formulas, where m is a number from 2 to about 200. g) compounds of the formula XII wherein R and R "have the meaning given under a).
- compositions containing compounds of the formula V in which R 4 has the meaning of hydrogen or alkyl having 1 to 4 C atoms and preferably the meaning of alkyl having 1 to 4 C atoms and in particular tert-butyl are particularly useful.
- R " Cs-C 18 alkyl and in particular iC 8 H 17 or iC 13 H 27 .
- Preferred alkyl groups for A are methyl, ethyl, propyl and butyl groups; methyl and tert-butyl are particularly preferred.
- A is the radical -CqH 2 qN (R ') (R ")
- typical examples are -CH 2 -N (C 1 -C 4 alkyl) 2 and especially -CH 2 -N (CH 3 ) 2 .
- the molar ratio of diphenylamine to diisobutylene can vary over a wide range, but is preferably kept in the range from 1: 1.11 to 1: 2.5, particularly preferably 1: 1.3 to 1: 1.75, in order to reduce the cost of To reduce the starting material and to keep the addition time of diisobutylene as short as possible.
- the compounds of the formula III are obtainable, for example, by reacting diphenylamine with sulfur (US 2,433,658).
- the compounds of the cyclic sterically hindered amine series are obtainable by processes which are known per se and which can be found in the relevant literature.
- compositions according to the present invention can contain A) a lubricant and, for example, 0.01 to 10% by weight, based on the composition, of a mixture of B), C) and D), as described above.
- 0.1 to 5% by weight, based on the composition, of a mixture of B), C) and D) is present.
- the mixture of B), C) and D) can contain, for example, 20 to 88% by weight of B), 10 to 60% by weight of C) and 2 to 20% by weight of D), the percentages are based on the mixture.
- B) 30 to 80% by weight, C) 10 to 60% by weight and D) 4 to 15% by weight are preferably present in the mixture of B), C) and D).
- 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 Hertzian normal stress is 2740 N / mm 2
- the maximum shear stress is 850 N / mm 2 .
- Ball and cylinder are made from the same tool steel.
- the process works according to the following principle:
- the PDSC cell (thermal analysis system 1090 from DuPont) consists of a heating block made of silver. In this heating block a constantan plate is inserted, which contains the thermocouples (Chromel-Alumel). Sample pans and reference pans are placed on the slightly elevated thermocouples. The interior of the DSC cell is covered with a thin gold film (corrosion protection). The reference pan remains empty, three drops of the respective formulation are poured into the sample pan. The temperature difference between sample and reference pans is determined under isothermal conditions. The enthalpy change dH / dt is given in mW. All measurements are carried out in air containing 400 ppm NO x . The pressure is 8 bar.
- Aral RL 136 a commercially available "black sludge reference oil", is used as the base oil. In order to increase the susceptibility to oxidation of the oil, 1% 1-decene is added to this oil.
- the concentration of the added additives decreases continuously.
- the heat flow dQ / dt increases.
- the time that passes until this increase occurs is called the induction time (onset). Accordingly, long induction times indicate a high aging stability of the oils.
- the formulations characterized by PDSC are from Table 2 evident.
- Example 15 Thermal stabilization of a mineral oil.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH401889 | 1989-11-08 | ||
CH4018/89 | 1989-11-08 |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0432089A1 true EP0432089A1 (fr) | 1991-06-12 |
EP0432089B1 EP0432089B1 (fr) | 1996-09-04 |
Family
ID=4268282
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP90810831A Expired - Lifetime EP0432089B1 (fr) | 1989-11-08 | 1990-10-30 | Compositions lubrifiantes |
Country Status (6)
Country | Link |
---|---|
US (1) | US5167844A (fr) |
EP (1) | EP0432089B1 (fr) |
JP (1) | JPH03168297A (fr) |
CA (1) | CA2029402A1 (fr) |
DE (1) | DE59010484D1 (fr) |
ES (1) | ES2091236T3 (fr) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2671354A1 (fr) * | 1991-01-08 | 1992-07-10 | Ciba Geigy Ag | Compositions lubrifiantes renfermant une association de stabilisants. |
EP0716141A3 (fr) * | 1994-12-07 | 1996-07-24 | Nippon Oil Co Ltd | |
EP0781834A3 (fr) * | 1995-12-28 | 1997-08-20 | Nippon Oil Co Ltd | Composition d'huile lubrifiante |
WO2009013275A1 (fr) * | 2007-07-23 | 2009-01-29 | Shell Internationale Research Maatschappij B.V. | Composition lubrifiante destinée à être utilisée dans des moteurs diesel compatibles avec un biocarburant |
CN114657545A (zh) * | 2021-03-12 | 2022-06-24 | 塞尔纳新材料(武汉)有限公司 | 一种生态除鳞型快速沉降钝化液及其制备工艺 |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE4138481A1 (de) * | 1991-11-22 | 1993-05-27 | Kempten Elektroschmelz Gmbh | Wiederaufarbeitung von gebrauchten verdampferschiffchen |
JP2859077B2 (ja) * | 1993-04-09 | 1999-02-17 | 出光興産株式会社 | 潤滑油組成物 |
JP3527555B2 (ja) * | 1994-12-09 | 2004-05-17 | 出光興産株式会社 | 熱処理油組成物 |
JP3508785B2 (ja) * | 1994-12-13 | 2004-03-22 | 出光興産株式会社 | ギヤ用潤滑油組成物 |
JP3527556B2 (ja) * | 1994-12-14 | 2004-05-17 | 出光興産株式会社 | 内燃機関用潤滑油組成物 |
GB0011189D0 (en) * | 2000-05-10 | 2000-06-28 | Great Lakes Chemical Europ | Anti-oxidant additives |
BR0310057A (pt) | 2002-05-17 | 2007-04-10 | Othera Pharmaceuticals Inc | melhoria do desenvolvimento de catarata e outras doenças oftálmicas |
US6797677B2 (en) | 2002-05-30 | 2004-09-28 | Afton Chemical Corporation | Antioxidant combination for oxidation and deposit control in lubricants containing molybdenum and alkylated phenothiazine |
US6599865B1 (en) | 2002-07-12 | 2003-07-29 | Ethyl Corporation | Effective antioxidant combination for oxidation and deposit control in crankcase lubricants |
US7825134B2 (en) | 2003-05-19 | 2010-11-02 | Othera Holding, Inc. | Amelioration of cataracts, macular degeneration and other ophthalmic diseases |
US8466096B2 (en) * | 2007-04-26 | 2013-06-18 | Afton Chemical Corporation | 1,3,2-dioxaphosphorinane, 2-sulfide derivatives for use as anti-wear additives in lubricant compositions |
RU2493243C2 (ru) * | 2009-02-02 | 2013-09-20 | Ар.Ти. ВАНДЕРБИЛТ КОМПАНИ, ИНК. | Беззольная смазывающая композиция |
US8716359B2 (en) * | 2010-03-18 | 2014-05-06 | Vanderbilt Chemicals, Llc | Polyurethane foam scorch inhibitor |
Citations (5)
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DE2364121A1 (de) * | 1972-12-27 | 1974-07-11 | Ciba Geigy Ag | Verfahren zur herstellung von hydroxyalkylphenylderivaten |
EP0059168A1 (fr) * | 1981-02-19 | 1982-09-01 | Ciba-Geigy Ag | Elastomères organiques et huiles lubrifiantes minérales et synthétiques contenant des esters phénolmercaptocarboxyliques comme stabilisants |
EP0267875A2 (fr) * | 1986-11-11 | 1988-05-18 | Ciba-Geigy Ag | Composition lubrifiante pour haute température |
EP0346283A2 (fr) * | 1988-06-09 | 1989-12-13 | Ciba-Geigy Ag | Composition lubrifiante |
EP0356677A1 (fr) * | 1988-07-18 | 1990-03-07 | Ciba-Geigy Ag | Composition lubrifiante |
Family Cites Families (7)
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US2758086A (en) * | 1952-06-28 | 1956-08-07 | California Research Corp | Lubricant composition |
US3412118A (en) * | 1962-08-31 | 1968-11-19 | Hooker Chemical Corp | Salts of 2, 6-and 2, 4, 6-substituted primary aryl phosphites |
DE1594405B2 (de) * | 1966-07-20 | 1974-03-07 | Deutsche Shell Ag, 2000 Hamburg | Schmieröl |
US3791985A (en) * | 1970-10-13 | 1974-02-12 | Gaf Corp | Lubricating compositions containing sulfur containing phosphate esters |
US3951829A (en) * | 1975-05-05 | 1976-04-20 | Cities Service Company | Two-cycle and rotary combustion engine lubricant |
US4085132A (en) * | 1975-06-24 | 1978-04-18 | Ciba-Geigy Corporation | Process for the production of hydroxyalkylphenyl derivatives |
GB8607157D0 (en) * | 1986-03-22 | 1986-04-30 | Ciba Geigy Ag | Lubricating compositions |
-
1990
- 1990-10-30 ES ES90810831T patent/ES2091236T3/es not_active Expired - Lifetime
- 1990-10-30 DE DE59010484T patent/DE59010484D1/de not_active Expired - Fee Related
- 1990-10-30 EP EP90810831A patent/EP0432089B1/fr not_active Expired - Lifetime
- 1990-10-31 US US07/606,401 patent/US5167844A/en not_active Expired - Fee Related
- 1990-11-06 CA CA002029402A patent/CA2029402A1/fr not_active Abandoned
- 1990-11-08 JP JP2303732A patent/JPH03168297A/ja active Pending
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2364121A1 (de) * | 1972-12-27 | 1974-07-11 | Ciba Geigy Ag | Verfahren zur herstellung von hydroxyalkylphenylderivaten |
EP0059168A1 (fr) * | 1981-02-19 | 1982-09-01 | Ciba-Geigy Ag | Elastomères organiques et huiles lubrifiantes minérales et synthétiques contenant des esters phénolmercaptocarboxyliques comme stabilisants |
EP0267875A2 (fr) * | 1986-11-11 | 1988-05-18 | Ciba-Geigy Ag | Composition lubrifiante pour haute température |
EP0346283A2 (fr) * | 1988-06-09 | 1989-12-13 | Ciba-Geigy Ag | Composition lubrifiante |
EP0356677A1 (fr) * | 1988-07-18 | 1990-03-07 | Ciba-Geigy Ag | Composition lubrifiante |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2671354A1 (fr) * | 1991-01-08 | 1992-07-10 | Ciba Geigy Ag | Compositions lubrifiantes renfermant une association de stabilisants. |
BE1004925A5 (fr) * | 1991-01-08 | 1993-02-23 | Ciba Geigy Ag | Compositions lubrifiantes renfermant une association de stabilisants. |
EP0716141A3 (fr) * | 1994-12-07 | 1996-07-24 | Nippon Oil Co Ltd | |
EP0781834A3 (fr) * | 1995-12-28 | 1997-08-20 | Nippon Oil Co Ltd | Composition d'huile lubrifiante |
US5912212A (en) * | 1995-12-28 | 1999-06-15 | Nippon Oil Co., Ltd. | Lubricating oil composition |
WO2009013275A1 (fr) * | 2007-07-23 | 2009-01-29 | Shell Internationale Research Maatschappij B.V. | Composition lubrifiante destinée à être utilisée dans des moteurs diesel compatibles avec un biocarburant |
CN114657545A (zh) * | 2021-03-12 | 2022-06-24 | 塞尔纳新材料(武汉)有限公司 | 一种生态除鳞型快速沉降钝化液及其制备工艺 |
CN114657545B (zh) * | 2021-03-12 | 2023-11-24 | 塞尔纳新材料(武汉)有限公司 | 一种生态除鳞型快速沉降钝化液及其制备工艺 |
Also Published As
Publication number | Publication date |
---|---|
EP0432089B1 (fr) | 1996-09-04 |
ES2091236T3 (es) | 1996-11-01 |
US5167844A (en) | 1992-12-01 |
CA2029402A1 (fr) | 1991-05-09 |
DE59010484D1 (de) | 1996-10-10 |
JPH03168297A (ja) | 1991-07-22 |
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