JP2019524903A5 - - Google Patents
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- Publication number
- JP2019524903A5 JP2019524903A5 JP2018558684A JP2018558684A JP2019524903A5 JP 2019524903 A5 JP2019524903 A5 JP 2019524903A5 JP 2018558684 A JP2018558684 A JP 2018558684A JP 2018558684 A JP2018558684 A JP 2018558684A JP 2019524903 A5 JP2019524903 A5 JP 2019524903A5
- Authority
- JP
- Japan
- Prior art keywords
- lubricating oil
- oil composition
- group
- substituted
- linear
- 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 claims description 69
- 239000010687 lubricating oil Substances 0.000 claims description 55
- 239000003963 antioxidant agent Substances 0.000 claims description 34
- 125000006659 (C1-C20) hydrocarbyl group Chemical group 0.000 claims description 28
- 230000003078 antioxidant effect Effects 0.000 claims description 28
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 25
- 150000001412 amines Chemical class 0.000 claims description 20
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims description 19
- BRESEFMHKFGSDY-UHFFFAOYSA-N molybdenum;pyrrolidine-2,5-dione Chemical compound [Mo].O=C1CCC(=O)N1 BRESEFMHKFGSDY-UHFFFAOYSA-N 0.000 claims description 9
- -1 amine phosphates Chemical class 0.000 claims description 8
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- 229910052698 phosphorus Inorganic materials 0.000 claims description 7
- 239000011574 phosphorus Substances 0.000 claims description 7
- 150000003017 phosphorus Chemical class 0.000 claims description 6
- 229910019142 PO4 Inorganic materials 0.000 claims description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 230000001050 lubricating effect Effects 0.000 claims description 5
- 235000021317 phosphate Nutrition 0.000 claims description 5
- 150000002989 phenols Chemical class 0.000 claims description 4
- QVXGKJYMVLJYCL-UHFFFAOYSA-N 2,3-di(nonyl)-N-phenylaniline Chemical compound C(CCCCCCCC)C=1C(=C(C=CC1)NC1=CC=CC=C1)CCCCCCCCC QVXGKJYMVLJYCL-UHFFFAOYSA-N 0.000 claims description 3
- JWXNJZPOYUARDX-UHFFFAOYSA-N 2-tert-butyl-n-phenyl-n-(2,4,4-trimethylpentan-2-yl)aniline Chemical compound C=1C=CC=C(C(C)(C)C)C=1N(C(C)(C)CC(C)(C)C)C1=CC=CC=C1 JWXNJZPOYUARDX-UHFFFAOYSA-N 0.000 claims description 3
- UUNBFTCKFYBASS-UHFFFAOYSA-N C(CCCCCCC)C=1C(=C(C=CC1)NC1=CC=CC=C1)CCCCCCCC Chemical compound C(CCCCCCC)C=1C(=C(C=CC1)NC1=CC=CC=C1)CCCCCCCC UUNBFTCKFYBASS-UHFFFAOYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 239000003921 oil Substances 0.000 claims description 3
- 125000005541 phosphonamide group Chemical group 0.000 claims description 3
- 150000008039 phosphoramides Chemical class 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 230000002195 synergetic effect Effects 0.000 claims description 3
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 claims description 2
- 229930185605 Bisphenol Natural products 0.000 claims description 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical group [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- 238000005299 abrasion Methods 0.000 claims description 2
- 150000001336 alkenes Chemical class 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- 150000002990 phenothiazines Chemical class 0.000 claims description 2
- 125000005538 phosphinite group Chemical group 0.000 claims description 2
- 229920001021 polysulfide Polymers 0.000 claims description 2
- 239000005077 polysulfide Substances 0.000 claims description 2
- 150000008117 polysulfides Polymers 0.000 claims description 2
- 230000000153 supplemental effect Effects 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 239000011701 zinc Substances 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 4
- 238000000034 method Methods 0.000 claims 2
- RNBMWJIBIBMXDK-UHFFFAOYSA-N 2,3-dibutyl-N-phenylaniline Chemical compound C(CCC)C=1C(=C(C=CC1)NC1=CC=CC=C1)CCCC RNBMWJIBIBMXDK-UHFFFAOYSA-N 0.000 claims 1
- 239000007800 oxidant agent Substances 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims 1
- 150000003003 phosphines Chemical class 0.000 claims 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 claims 1
- 150000003013 phosphoric acid derivatives Chemical group 0.000 claims 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- SRENRFDRXNVMKN-UHFFFAOYSA-N n-butyl-n-phenylaniline Chemical compound C=1C=CC=CC=1N(CCCC)C1=CC=CC=C1 SRENRFDRXNVMKN-UHFFFAOYSA-N 0.000 description 1
- LVZUNTGFCXNQAF-UHFFFAOYSA-N n-nonyl-n-phenylaniline Chemical compound C=1C=CC=CC=1N(CCCCCCCCC)C1=CC=CC=C1 LVZUNTGFCXNQAF-UHFFFAOYSA-N 0.000 description 1
- RQVGZVZFVNMBGS-UHFFFAOYSA-N n-octyl-n-phenylaniline Chemical compound C=1C=CC=CC=1N(CCCCCCCC)C1=CC=CC=C1 RQVGZVZFVNMBGS-UHFFFAOYSA-N 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- MDDUHVRJJAFRAU-YZNNVMRBSA-N tert-butyl-[(1r,3s,5z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane Chemical compound C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)C(=C)\C1=C/CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MDDUHVRJJAFRAU-YZNNVMRBSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US15/209,272 | 2016-07-13 | ||
| US15/209,272 US10077410B2 (en) | 2016-07-13 | 2016-07-13 | Synergistic lubricating oil composition containing mixture of antioxidants |
| PCT/US2017/022707 WO2018013181A1 (en) | 2016-07-13 | 2017-03-16 | Synergistic lubricating oil composition containing mixture of antioxidants |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2019524903A JP2019524903A (ja) | 2019-09-05 |
| JP2019524903A5 true JP2019524903A5 (enExample) | 2020-04-23 |
| JP6711926B2 JP6711926B2 (ja) | 2020-06-17 |
Family
ID=58428410
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018558684A Active JP6711926B2 (ja) | 2016-07-13 | 2017-03-16 | 酸化防止剤の混合物を含有する相乗的潤滑油組成物 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US10077410B2 (enExample) |
| EP (1) | EP3484983B1 (enExample) |
| JP (1) | JP6711926B2 (enExample) |
| CN (1) | CN109196079B (enExample) |
| CA (1) | CA3020510A1 (enExample) |
| SG (1) | SG11201809691QA (enExample) |
| WO (1) | WO2018013181A1 (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11339345B2 (en) * | 2020-02-28 | 2022-05-24 | Vanderbilt Chemicals, Llc | Liquid octylated phenyl-α-naphthylamine composition |
Family Cites Families (48)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2346156A (en) | 1942-02-16 | 1944-04-11 | Standard Oil Co | Compounded lubricant |
| US2451642A (en) | 1944-10-23 | 1948-10-19 | Standard Oil Co | Viscous mineral oil compositions |
| US2718501A (en) | 1952-03-01 | 1955-09-20 | California Research Corp | Oils stable against oxidation |
| US2883362A (en) | 1953-12-30 | 1959-04-21 | Universal Oil Prod Co | Preventing the cracking of rubber by means of certain n,n,n',n'-tetra-alkyl-p-phenylene diamines |
| US2857424A (en) | 1955-08-25 | 1958-10-21 | Universal Oil Prod Co | Preparation of oxalic acid salts of phenylene diamines |
| GB835826A (en) | 1957-11-19 | 1960-05-25 | Firestone Tire & Rubber Co | Improvements relating to reaction products of hydrocarbon dihalides and substituted phenylenediamines and their use in rubber |
| DE1248643B (de) | 1959-03-30 | 1967-08-31 | The Lubrizol Corporation, Cleveland, Ohio (V. St. A.) | Verfahren zur Herstellung von öllöslichen aeylierten Aminen |
| DE1158496B (de) | 1961-01-20 | 1963-12-05 | Bayer Ag | Verfahren zur Herstellung von N, N', N'-trisubstituierten p-Phenylendiaminen |
| US3402201A (en) | 1963-03-04 | 1968-09-17 | Universal Oil Prod Co | N-cyclooctyl-alkyl-anilines |
| US3272746A (en) | 1965-11-22 | 1966-09-13 | Lubrizol Corp | Lubricating composition containing an acylated nitrogen compound |
| US3480635A (en) | 1966-09-28 | 1969-11-25 | Universal Oil Prod Co | N-piperidyl substituted phenylenediamines |
| GB1296592A (enExample) | 1969-06-26 | 1972-11-15 | ||
| US4031016A (en) | 1975-12-15 | 1977-06-21 | Shell Oil Company | Base oil compositions having improved light stability |
| US4320019A (en) | 1978-04-17 | 1982-03-16 | The Lubrizol Corporation | Multi-purpose additive compositions and concentrates containing same |
| US4263152A (en) | 1979-06-28 | 1981-04-21 | Chevron Research Company | Process of preparing molybdenum complexes, the complexes so-produced and lubricants containing same |
| US5359069A (en) | 1989-03-21 | 1994-10-25 | Ciba-Geigy Corporation | Non-migrating 1-hydrocarbyloxy hindered amine derivatives as polymer stabilizers |
| US5268113A (en) | 1989-07-07 | 1993-12-07 | Ciba-Geigy Corporation | Lubricant composition |
| BE1004925A5 (fr) | 1991-01-08 | 1993-02-23 | Ciba Geigy Ag | Compositions lubrifiantes renfermant une association de stabilisants. |
| TW270126B (enExample) | 1993-07-13 | 1996-02-11 | Ciba Geigy | |
| TW270131B (enExample) | 1993-07-13 | 1996-02-11 | Ciba Geigy | |
| TW267178B (enExample) | 1993-07-13 | 1996-01-01 | Ciba Geigy | |
| KR100340920B1 (ko) * | 1993-12-23 | 2002-12-05 | 시바 스페셜티 케미칼스 홀딩 인크. | 알킬화디페닐아민및페노티아진을포함하는반응생성물및이를함유하는조성물 |
| USRE38929E1 (en) * | 1995-11-20 | 2006-01-03 | Afton Chemical Intangibles Llc | Lubricant containing molybdenum compound and secondary diarylamine |
| US5962683A (en) | 1996-06-28 | 1999-10-05 | Ciba Specialty Chemicals Corp. | Oxazoline compounds as stabilizers |
| US6521681B1 (en) | 1996-07-05 | 2003-02-18 | Ciba Specialty Chemicals Corporation | Phenol-free stabilization of polyolefin fibres |
| US5711767A (en) | 1996-07-11 | 1998-01-27 | Ciba Specialty Chemicals Corporation | Stabilizers for the prevention of gum formation in gasoline |
| EP0873991A1 (de) | 1997-04-23 | 1998-10-28 | Ciba SC Holding AG | Polyalkylenglykolgruppen enthaltende gehinderte Amine als Stabilisatoren |
| GB2332678B (en) | 1997-12-23 | 2000-09-27 | Ciba Sc Holding Ag | Stabilizer mixtures containing a sterically hindered amine |
| US6174842B1 (en) * | 1999-03-30 | 2001-01-16 | Ethyl Corporation | Lubricants containing molybdenum compounds, phenates and diarylamines |
| AU6601001A (en) | 2000-05-31 | 2001-12-11 | Ciba Sc Holding Ag | Stabilizer mixtures |
| JP4170648B2 (ja) | 2002-03-29 | 2008-10-22 | 新日本石油株式会社 | 内燃機関用潤滑油組成物 |
| US6962896B2 (en) | 2002-05-31 | 2005-11-08 | Chevron Oronite Company Llc | Reduced color molybdenum-containing composition and a method of making same |
| US6696393B1 (en) | 2002-08-01 | 2004-02-24 | Chevron Oronite Company Llc | Methods and compositions for reducing wear in internal combustion engines lubricated with a low phosphorus content lubricating oil |
| CA2559746C (en) * | 2004-04-01 | 2013-06-25 | Ciba Specialty Chemicals Holding Inc. | Alkylated pana and dpa compositions |
| US7875576B2 (en) * | 2004-07-29 | 2011-01-25 | Chevron Oronite Company Llc | Lubricating oil composition for internal combustion engines |
| US7704931B2 (en) | 2004-12-10 | 2010-04-27 | Chemtura Corporation | Lubricant compositions stabilized with multiple antioxidants |
| EP1861484A2 (en) | 2005-02-22 | 2007-12-05 | Polnox Corporation | Nitrogen and hindered phenol containing dual functional macromolecular antioxidants: synthesis , performances and applications |
| US8741824B2 (en) | 2005-07-08 | 2014-06-03 | Infineum International Limited | EGR equipped diesel engines and lubricating oil compositions |
| US7501386B2 (en) * | 2005-12-21 | 2009-03-10 | Chevron Oronite Company, Llc | Synergistic lubricating oil composition containing a mixture of a benzo[b]perhydroheterocyclic arylamine and a diarylamine |
| US7932218B2 (en) | 2006-07-31 | 2011-04-26 | Ciba Corporation | Lubricant composition |
| WO2008109523A1 (en) | 2007-03-06 | 2008-09-12 | R.T. Vanderbilt Company, Inc. | Lubricant antioxidant compositions containing a metal compound and a hindered amine |
| US7683017B2 (en) | 2007-06-20 | 2010-03-23 | Chevron Oronite Company Llc | Synergistic lubricating oil composition containing a mixture of a nitro-substituted diarylamine and a diarylamine |
| US20090156441A1 (en) * | 2007-12-12 | 2009-06-18 | Rowland Robert G | Cycloalkyl phenylenediamines as deposit control agents for lubricants |
| US8022022B2 (en) * | 2008-06-30 | 2011-09-20 | Chevron Oronite Company Llc | Lubricating oil additive and lubricating oil composition containing same |
| US8022023B2 (en) * | 2008-06-30 | 2011-09-20 | Chevron Oronite Company Llc | Lubricating oil additive and lubricating oil composition containing same |
| US8426608B2 (en) * | 2011-01-21 | 2013-04-23 | Chevron Oronite Company Llc | Process for preparation of high molecular weight molybdenum succinimide complexes |
| US8987515B2 (en) * | 2011-12-13 | 2015-03-24 | Chemtura Corporation | Cross products and co-oligomers of phenylenediamines and aromatic amines as antioxidants for lubricants |
| CN104662138B (zh) * | 2012-07-27 | 2016-09-21 | 吉坤日矿日石能源株式会社 | 润滑油组合物及同时抑制铜和铅溶出的滑动材料的润滑方法 |
-
2016
- 2016-07-13 US US15/209,272 patent/US10077410B2/en active Active
-
2017
- 2017-03-16 CA CA3020510A patent/CA3020510A1/en active Pending
- 2017-03-16 JP JP2018558684A patent/JP6711926B2/ja active Active
- 2017-03-16 EP EP17714116.5A patent/EP3484983B1/en active Active
- 2017-03-16 WO PCT/US2017/022707 patent/WO2018013181A1/en not_active Ceased
- 2017-03-16 SG SG11201809691QA patent/SG11201809691QA/en unknown
- 2017-03-16 CN CN201780033179.2A patent/CN109196079B/zh active Active
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