WO1995016765B1 - Composition pour la stabilisation des lubrifiants esters synthetiques - Google Patents
Composition pour la stabilisation des lubrifiants esters synthetiquesInfo
- Publication number
- WO1995016765B1 WO1995016765B1 PCT/US1994/014539 US9414539W WO9516765B1 WO 1995016765 B1 WO1995016765 B1 WO 1995016765B1 US 9414539 W US9414539 W US 9414539W WO 9516765 B1 WO9516765 B1 WO 9516765B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- diphenylamine
- aryl
- naphthylamine
- alkyl
- styryl
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract 19
- 150000002148 esters Chemical class 0.000 title claims 2
- 239000000314 lubricant Substances 0.000 title claims 2
- 239000003381 stabilizer Substances 0.000 title abstract 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N Diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims abstract 19
- 230000003078 antioxidant Effects 0.000 claims abstract 13
- 239000003963 antioxidant agent Substances 0.000 claims abstract 13
- 125000005504 styryl group Chemical group 0.000 claims abstract 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract 10
- 239000007795 chemical reaction product Substances 0.000 claims abstract 7
- 125000004432 carbon atoms Chemical group C* 0.000 claims abstract 5
- 150000001451 organic peroxides Chemical class 0.000 claims abstract 5
- 238000006243 chemical reaction Methods 0.000 claims abstract 4
- 239000002904 solvent Substances 0.000 claims abstract 4
- 230000001590 oxidative Effects 0.000 claims abstract 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- 238000000034 method Methods 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 4
- 230000001721 combination Effects 0.000 claims 4
- -1 C8 alkyl radicals Chemical group 0.000 claims 3
- 150000001412 amines Chemical class 0.000 claims 2
- 230000015556 catabolic process Effects 0.000 claims 2
- 230000004059 degradation Effects 0.000 claims 2
- 238000006731 degradation reaction Methods 0.000 claims 2
- 239000010687 lubricating oil Substances 0.000 claims 2
- 229940003969 Adrenergic and dopaminergic agents combinations Drugs 0.000 claims 1
- 229940001019 Aluminium antacid compound combinations Drugs 0.000 claims 1
- 229940010996 Amide local anesthetic combinations Drugs 0.000 claims 1
- 229940084438 Antiinfective irrigating solution combinations Drugs 0.000 claims 1
- 229940095835 Beta-lactamase sensitive penicillin combinations Drugs 0.000 claims 1
- 229940001469 Calcium antacid compound combinations Drugs 0.000 claims 1
- 229940073688 Caries prophylactic agent combinations Drugs 0.000 claims 1
- 229940060167 Enema combinations Drugs 0.000 claims 1
- 229960003366 Hepatitis vaccine combinations Drugs 0.000 claims 1
- 229940031471 Imidazole and triazole derivative topical antifungal combinations Drugs 0.000 claims 1
- 229940000248 Intermediate-acting sulfonamide combinations Drugs 0.000 claims 1
- 229940107315 Local hemostatic combinations Drugs 0.000 claims 1
- 229940007270 Long-acting sulfonamide combinations Drugs 0.000 claims 1
- 229940000523 Magnesium antacid compound combinations Drugs 0.000 claims 1
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenylnaphthalen-1-amine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 claims 1
- 229940111336 Other anti-dementia drug combinations in ATC Drugs 0.000 claims 1
- 229940032419 Other antifungal combinations for topical use in ATC Drugs 0.000 claims 1
- 229940106059 Other intestinal adsorbent combinations in ATC Drugs 0.000 claims 1
- 229940076421 Other irrigating solution combinations in ATC Drugs 0.000 claims 1
- 229940097635 Penicillins with extended spectrum combinations Drugs 0.000 claims 1
- 229940001079 Platelet aggregation inhibitor combinations excl. heparin Drugs 0.000 claims 1
- 229940086052 Potassium supplement combinations Drugs 0.000 claims 1
- 229940084925 Salt solution combinations Drugs 0.000 claims 1
- 229940000628 Short-acting sulfonamide combinations Drugs 0.000 claims 1
- 229940036145 Specific immunoglobulin combinations Drugs 0.000 claims 1
- 235000010290 biphenyl Nutrition 0.000 claims 1
- 239000004305 biphenyl Substances 0.000 claims 1
- 125000006267 biphenyl group Chemical group 0.000 claims 1
- 229940086715 combination drugs used in erectile dysfunction Drugs 0.000 claims 1
- 239000010696 ester oil Substances 0.000 claims 1
- 229940050438 excl. combinations with cough suppressants expectorant combinations Drugs 0.000 claims 1
- 229940048784 expectorant combinations excluding combinations with cough suppressants Drugs 0.000 claims 1
- 229940050564 fast-acting combinations Insulins and analogs for injection Drugs 0.000 claims 1
- 229940090613 gonadotropin combinations Drugs 0.000 claims 1
- 229940052038 intermediate-acting combinations Insulins and analogs for injection Drugs 0.000 claims 1
- 229940052297 intermediate-acting combined with fast-acting- combinations Insulins and analogs for injection Drugs 0.000 claims 1
- 229940074591 local opthalmologic anesthetic combinations Drugs 0.000 claims 1
- 229940051883 long-acting insulins and analogs for injection combinations Drugs 0.000 claims 1
- 229940042835 lung surfactant combinations Drugs 0.000 claims 1
- 229940064925 opium alkaloids and derivative combination cough suppressants Drugs 0.000 claims 1
- 229940064347 other cough suppressant combinations in ATC Drugs 0.000 claims 1
- 229940021273 other nasal preparation combinations in ATC Drugs 0.000 claims 1
- 229940067531 otologic analgesic and anesthetic combinations Drugs 0.000 claims 1
- 230000036647 reaction Effects 0.000 claims 1
- 230000000087 stabilizing Effects 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 229940030476 topical antibiotic combinations Drugs 0.000 claims 1
- 229940022453 vitamin D and analog combinations Drugs 0.000 claims 1
- 239000000047 product Substances 0.000 abstract 2
- 238000005260 corrosion Methods 0.000 abstract 1
- 150000004985 diamines Chemical class 0.000 abstract 1
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
Abstract
L'invention décrit une composition de stabilisant antioxydant qui est le produit de la réaction d'une diphénylamine et d'une N-aryl-naphtylamine en présence d'un peroxyde organique. Le rapport molaire de la diphénylamine et de la N-aryl-naphtylamine varie entre 1/1 et 10/1. Il en résulte davantage de produits de réaction oligomères et sensiblement moins de réactifs monomères résiduels n'ayant pas subi de réaction. La composition produite résultante comprend des homo-oligomères de diphénylamine et des oligomères croisés de diphénylamine et N-aryl-naphtylamine. Il est intéressant que la diphénylamine et la N-aryl-naphtylamine soient substituées avec des groupes alcoyle possédant 1 à 20 atomes de carbone ou des groupes styryle. La température de réaction est de préférence de 130° à 150 °C environ. Les conditions de réaction contrôlées permettent d'utiliser des solvants possédant des atomes d'hydrogène qui peuvent être extraits, sans produire une déshydrocondensation significative entre le solvant et les diamines. Les produits de réaction ont une excellente résistance à l'oxydation lors de l'Essai de Stabilité à la Corrosion par Oxydation (OCS) et du Test de Coker en Phase Vapeur, par rapport aux produits de déshydrocondensation produits dans d'autres conditions.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE69405410T DE69405410T2 (de) | 1993-12-15 | 1994-12-15 | Stabilisatormischung für synthetisches estergleitmittel |
| CA002179169A CA2179169C (fr) | 1993-12-15 | 1994-12-15 | Composition pour la stabilisation des lubrifiants esters synthetiques |
| EP95911554A EP0734432B1 (fr) | 1993-12-15 | 1994-12-15 | Composition pour la stabilisation des lubrifiants esters synthetiques |
| JP51698195A JP3717513B2 (ja) | 1993-12-15 | 1994-12-15 | 合成エステル潤滑剤用安定剤組成物 |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16685193A | 1993-12-15 | 1993-12-15 | |
| US08/166,851 | 1993-12-15 |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| WO1995016765A2 WO1995016765A2 (fr) | 1995-06-22 |
| WO1995016765A3 WO1995016765A3 (fr) | 1995-07-27 |
| WO1995016765A9 WO1995016765A9 (fr) | 1995-08-24 |
| WO1995016765B1 true WO1995016765B1 (fr) | 1995-09-14 |
Family
ID=22604927
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US1994/014539 WO1995016765A2 (fr) | 1993-12-15 | 1994-12-15 | Composition pour la stabilisation des lubrifiants esters synthetiques |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US6426324B1 (fr) |
| EP (1) | EP0734432B1 (fr) |
| JP (1) | JP3717513B2 (fr) |
| AT (1) | ATE157697T1 (fr) |
| DE (1) | DE69405410T2 (fr) |
| WO (1) | WO1995016765A2 (fr) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5489711A (en) * | 1994-12-20 | 1996-02-06 | The B. F. Goodrich Company | Synthetic lubricant antioxidant from monosubstituted diphenylamines |
| AU7119300A (en) * | 1999-09-30 | 2001-04-30 | Noveon Ip Holdings Corp. | Method of manufacturing alkylated phenylnaphthylamine compositions; and products |
| CA2403540A1 (fr) * | 2001-11-20 | 2003-05-20 | Bp Corporation North America Inc. | Combinaison synergique d'antioxydants a base d'arylamine dans des huiles pour turbines d'avions |
| US20030232030A1 (en) * | 2002-06-12 | 2003-12-18 | L'oreal | Compositions containing at least one oil structured with at least one silicone-polyamide polymer, and at least one gelling agent and methods of using the same |
| EP1963470B1 (fr) * | 2005-12-16 | 2013-02-27 | Hatco Corporation | Préformulation d'additifs pour des lubrifiants synthétiques haute température |
| 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 |
| US8003583B2 (en) * | 2005-12-21 | 2011-08-23 | Chevron Oronite Company Llc | Benzo[b]perhydroheterocyclic arylamines and lubricating oil compositions |
| US7285518B2 (en) * | 2005-12-21 | 2007-10-23 | Chevron Oronite Company Llc | Dibenzo[b]perhydroheterocyclic amines and lubricating oil compositions |
| US7863227B2 (en) * | 2006-03-31 | 2011-01-04 | Exxonmobil Research And Engineering Company | High performance lubricant containing high molecular weight aromatic amine antioxidant and low boron content dispersant |
| US7413682B2 (en) | 2006-08-15 | 2008-08-19 | Anderol, Inc. | Antioxidants and methods of making antioxidants |
| US7307049B1 (en) * | 2007-02-08 | 2007-12-11 | Anderol, Inc. | Antioxidants for synthetic lubricants and methods and manufacture |
| 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 |
| FR2937047B1 (fr) | 2008-10-10 | 2012-07-27 | Nyco Sa | Utilisation d'un additif a base d'oligomeres pour stabiliser une composition lubrifiante pour chaine de convoyage |
| FR2946983B1 (fr) | 2009-06-23 | 2011-12-23 | Nyco | Agents anti-usure a neurotoxicite reduite |
| US8987515B2 (en) * | 2011-12-13 | 2015-03-24 | Chemtura Corporation | Cross products and co-oligomers of phenylenediamines and aromatic amines as antioxidants for lubricants |
| WO2013090051A1 (fr) * | 2011-12-13 | 2013-06-20 | Chemtura Corporation | Produits de réaction croisée et co-oligomères de phénylènediamines et d'amines aromatiques comme antioxydants pour lubrifiants |
| US10208269B2 (en) * | 2013-12-23 | 2019-02-19 | Exxonmobil Research And Engineering Company | Low viscosity ester lubricant and method for using |
| CA2955352C (fr) * | 2014-09-19 | 2018-11-13 | Vanderbilt Chemicals, Llc | Compositions de lubrifiant industriel a base de polyalkyleneglycol |
| CN105733740A (zh) * | 2014-12-08 | 2016-07-06 | 中国石油天然气股份有限公司 | 一种胺类低聚物抗氧剂及其制备方法 |
| US20180179463A1 (en) | 2016-12-22 | 2018-06-28 | Exxonmobil Research And Engineering Company | Aircraft turbine oil base stock and method of making |
| US20190093040A1 (en) * | 2017-09-22 | 2019-03-28 | Exxonmobil Research And Engineering Company | Lubricating oil compositions with viscosity and deposit control |
| CN107573983A (zh) * | 2017-10-23 | 2018-01-12 | 中国石油化工股份有限公司 | 一种耐高温抗氧剂及其制备方法和应用 |
| CA3094639A1 (fr) * | 2018-03-20 | 2019-09-26 | Basf Se | Composition lubrifiante |
| WO2020132164A1 (fr) | 2018-12-19 | 2020-06-25 | Exxonmobil Research And Engineering Company | Compositions d'huile lubrifiante avec contrôle de la viscosité |
| US20200199480A1 (en) | 2018-12-19 | 2020-06-25 | Exxonmobil Research And Engineering Company | Lubricating oil compositions with antioxidant formation and dissipation control |
| CA3131107A1 (fr) | 2019-03-20 | 2020-09-24 | Michael Hoey | Composition lubrifiante |
| FR3114816B1 (fr) | 2020-10-06 | 2022-10-21 | Nyco | Procédé continu de polymérisation ou d’oligomérisation de diphénylamines |
| CN114479987A (zh) * | 2020-10-26 | 2022-05-13 | 中国石油化工股份有限公司 | 胺类化合物及其制备方法、用途 |
| CN114426901A (zh) * | 2022-01-21 | 2022-05-03 | 中国石油化工股份有限公司 | 一种高温抗氧剂溶液及其制备方法 |
| FR3135091A1 (fr) | 2022-04-27 | 2023-11-03 | Nyco | Utilisation d’un antioxydant pour réduire et/ou prévenir la toxicité d’une composition lubrifiante |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3206405A (en) | 1962-01-02 | 1965-09-14 | Socony Mobil Oil Co Inc | Synthetic lubricants comprising dehydrocondensation products of polyesters |
| US3247111A (en) | 1963-04-08 | 1966-04-19 | Socony Mobil Oil Co | High temperature jet lubricant |
| US3573206A (en) * | 1966-03-28 | 1971-03-30 | Mobil Oil Corp | Lubricant compositions |
| US3509214A (en) * | 1966-03-28 | 1970-04-28 | Mobil Oil Corp | Oil soluble oxidized naphthylamine compositions |
| US3492233A (en) * | 1967-12-12 | 1970-01-27 | Mobil Oil Corp | Lubricant compositions containing dehydrocondensation products |
| GB1236740A (en) | 1969-04-11 | 1971-06-23 | Geigy Uk Ltd | Tertiary alkylated diphenylamines and their uses as antioxidants |
| BE756024A (nl) | 1969-09-22 | 1971-03-11 | Shell Int Research | Alkyl-gesubstitueerde fenylnaftylaminen en smeermiddelcomposities die deze bevatten |
| US3759996A (en) | 1971-01-13 | 1973-09-18 | Mobil Oil Corp | Process for dimerizing diarylamines |
| GB1393366A (en) | 1971-10-06 | 1975-05-07 | Exxon Research Engineering Co | Antioxidants |
| US3773665A (en) * | 1971-11-17 | 1973-11-20 | Mobil Oil Corp | Lubricants containing amine antioxidants |
| JP2587296B2 (ja) * | 1989-09-08 | 1997-03-05 | 日本石油株式会社 | 潤滑油組成物 |
| US5489711A (en) * | 1994-12-20 | 1996-02-06 | The B. F. Goodrich Company | Synthetic lubricant antioxidant from monosubstituted diphenylamines |
-
1994
- 1994-12-15 WO PCT/US1994/014539 patent/WO1995016765A2/fr active IP Right Grant
- 1994-12-15 EP EP95911554A patent/EP0734432B1/fr not_active Expired - Lifetime
- 1994-12-15 DE DE69405410T patent/DE69405410T2/de not_active Expired - Fee Related
- 1994-12-15 AT AT95911554T patent/ATE157697T1/de not_active IP Right Cessation
- 1994-12-15 JP JP51698195A patent/JP3717513B2/ja not_active Expired - Fee Related
-
2000
- 2000-10-25 US US09/696,617 patent/US6426324B1/en not_active Expired - Fee Related
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