DE69738259T2 - Oxidationsstabilisierte Schmieröle und Polyol-Lösungen - Google Patents
Oxidationsstabilisierte Schmieröle und Polyol-Lösungen Download PDFInfo
- Publication number
- DE69738259T2 DE69738259T2 DE69738259T DE69738259T DE69738259T2 DE 69738259 T2 DE69738259 T2 DE 69738259T2 DE 69738259 T DE69738259 T DE 69738259T DE 69738259 T DE69738259 T DE 69738259T DE 69738259 T2 DE69738259 T2 DE 69738259T2
- Authority
- DE
- Germany
- Prior art keywords
- diphenylamine
- less
- weight
- unsubstituted
- reaction
- 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.)
- Expired - Fee Related
Links
- 229920005862 polyol Polymers 0.000 title claims description 16
- 150000003077 polyols Chemical class 0.000 title claims description 16
- 239000010687 lubricating oil Substances 0.000 title description 6
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims abstract description 402
- 239000004927 clay Substances 0.000 claims abstract description 57
- FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical group CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 claims abstract description 51
- 239000003054 catalyst Substances 0.000 claims abstract description 41
- 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 abstract description 32
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 29
- 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 abstract description 28
- 239000000203 mixture Substances 0.000 claims abstract description 19
- 230000002152 alkylating effect Effects 0.000 claims abstract description 9
- 238000000034 method Methods 0.000 claims description 39
- 238000006243 chemical reaction Methods 0.000 claims description 38
- 239000002253 acid Substances 0.000 claims description 12
- HXRAIVCWVIJIKB-UHFFFAOYSA-N 2-butyl-n-octyl-n-phenylaniline Chemical compound C=1C=CC=C(CCCC)C=1N(CCCCCCCC)C1=CC=CC=C1 HXRAIVCWVIJIKB-UHFFFAOYSA-N 0.000 claims description 7
- SRENRFDRXNVMKN-UHFFFAOYSA-N n-butyl-n-phenylaniline Chemical compound C=1C=CC=CC=1N(CCCC)C1=CC=CC=C1 SRENRFDRXNVMKN-UHFFFAOYSA-N 0.000 claims description 7
- MEIQSUIILRYXCS-UHFFFAOYSA-N C(CCC)C1=CC=C(C=C1)N(CCCCCCCC)C1=CC=CC=C1 Chemical compound C(CCC)C1=CC=C(C=C1)N(CCCCCCCC)C1=CC=CC=C1 MEIQSUIILRYXCS-UHFFFAOYSA-N 0.000 claims description 5
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical class O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 claims description 5
- 230000003647 oxidation Effects 0.000 claims description 3
- 238000007254 oxidation reaction Methods 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 238000005804 alkylation reaction Methods 0.000 description 51
- 150000001336 alkenes Chemical class 0.000 description 47
- 230000029936 alkylation Effects 0.000 description 32
- 239000000047 product Substances 0.000 description 28
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 22
- 239000004711 α-olefin Substances 0.000 description 18
- 239000003963 antioxidant agent Substances 0.000 description 14
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 12
- 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 12
- -1 monosubstituted diphenylamine Chemical class 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 7
- 238000004817 gas chromatography Methods 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 239000000376 reactant Substances 0.000 description 7
- 230000035484 reaction time Effects 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 4
- 230000003078 antioxidant effect Effects 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000004383 yellowing Methods 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 239000007806 chemical reaction intermediate Substances 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 229910052901 montmorillonite Inorganic materials 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 238000007711 solidification Methods 0.000 description 2
- 230000008023 solidification Effects 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- BGHCVCJVXZWKCC-UHFFFAOYSA-N tetradecane Chemical compound CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 1
- 229920000459 Nitrile rubber Polymers 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical group [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 229910004283 SiO 4 Inorganic materials 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical group 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910000323 aluminium silicate Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 235000012216 bentonite Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- NTXGQCSETZTARF-UHFFFAOYSA-N buta-1,3-diene;prop-2-enenitrile Chemical compound C=CC=C.C=CC#N NTXGQCSETZTARF-UHFFFAOYSA-N 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000002734 clay mineral Substances 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000010696 ester oil Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000002085 irritant Substances 0.000 description 1
- 231100000021 irritant Toxicity 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000010525 oxidative degradation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/60—Preparation of compounds containing amino groups bound to a carbon skeleton by condensation or addition reactions, e.g. Mannich reaction, addition of ammonia or amines to alkenes or to alkynes or addition of compounds containing an active hydrogen atom to Schiff's bases, quinone imines, or aziranes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/16—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing nitrogen
- C09K15/18—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing nitrogen containing an amine or imine moiety
-
- 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
- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
- C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M133/12—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M177/00—Special methods of preparation of lubricating compositions; Chemical modification by after-treatment of components or of the whole of a lubricating composition, not covered by other classes
-
- 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
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
- C10M2215/064—Di- and triaryl amines
-
- 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
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/10—Inhibition of oxidation, e.g. anti-oxidants
-
- 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
- C10N2070/00—Specific manufacturing methods for lubricant compositions
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Lubricants (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US655511 | 1996-05-30 | ||
| US08/655,511 US5750787A (en) | 1995-09-13 | 1996-05-30 | Liquid alkylated diphenylamine antioxidant |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69738259D1 DE69738259D1 (de) | 2007-12-13 |
| DE69738259T2 true DE69738259T2 (de) | 2008-08-14 |
Family
ID=24629188
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69727323T Expired - Fee Related DE69727323T2 (de) | 1996-05-30 | 1997-05-30 | Flüssiges alkyliertes Diphenylaminantioxidant |
| DE69710638T Expired - Fee Related DE69710638T2 (de) | 1996-05-30 | 1997-05-30 | Flüssiges alkyliertes Diphenylaminantioxidant |
| DE69738259T Expired - Fee Related DE69738259T2 (de) | 1996-05-30 | 1997-05-30 | Oxidationsstabilisierte Schmieröle und Polyol-Lösungen |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69727323T Expired - Fee Related DE69727323T2 (de) | 1996-05-30 | 1997-05-30 | Flüssiges alkyliertes Diphenylaminantioxidant |
| DE69710638T Expired - Fee Related DE69710638T2 (de) | 1996-05-30 | 1997-05-30 | Flüssiges alkyliertes Diphenylaminantioxidant |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US5750787A (enExample) |
| EP (3) | EP1411044B1 (enExample) |
| JP (1) | JP4116114B2 (enExample) |
| AT (3) | ATE376990T1 (enExample) |
| CA (1) | CA2206429C (enExample) |
| DE (3) | DE69727323T2 (enExample) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SG65759A1 (en) * | 1997-06-06 | 1999-06-22 | Ciba Sc Holding Ag | Nonylated diphenylamines |
| US6204412B1 (en) * | 1999-04-16 | 2001-03-20 | The B. F. Goodrich Company | Method of manufacturing alkylated diphenylamine compositions and products thereof |
| EP1067124A1 (de) * | 1999-07-09 | 2001-01-10 | Ciba SC Holding AG | Verfahren zur Herstellung eines Gemisches von alkylierten Phenothiazinen und Diphenylaminen |
| US6355839B1 (en) | 2001-08-31 | 2002-03-12 | Chevron U.S.A., Inc. | Alkylation of diphenylamine with polyisobutylene oligomers |
| US6891053B2 (en) * | 2001-10-02 | 2005-05-10 | Noveon Ip Holdings Corp. | Method of making oleochemical oil-based polyols |
| US7189875B2 (en) * | 2003-04-04 | 2007-03-13 | Crompton Corporation | Diphenylamine alkylated with olefin mixtures containing fractions with varying degrees of activity |
| US6930183B2 (en) * | 2003-04-17 | 2005-08-16 | Crompton Corporation | Alkylated iminodibenzyls as antioxidants |
| SK14562003A3 (sk) * | 2003-11-25 | 2005-06-02 | Duslo,A.S. | Antioxidačné kompozície oktylovaných difenylamínov a spôsob ich výroby |
| CN100338197C (zh) * | 2004-11-26 | 2007-09-19 | 吉林正基科技开发有限责任公司 | 聚苯胺防锈金属切削液 |
| US7390928B2 (en) * | 2005-12-14 | 2008-06-24 | Chemtura Corporation | Alkylation of N′-phenyl-N-alkylphenylenediamines in ionic liquid, N′-phenyl-N-alkyl (alkylphenylene) diamines produced thereby, and lubricant compositions containing same |
| US7145038B1 (en) | 2005-12-14 | 2006-12-05 | Chemtura Corporation | Alkylation of a diphenylamine compound in ionic liquid |
| US8828916B2 (en) | 2006-12-28 | 2014-09-09 | Chevron Oronite Company Llc | Method to prepare nonylated diphenylamine using recycle sequential temperatures |
| RU2346029C2 (ru) * | 2007-03-27 | 2009-02-10 | Открытое акционерное общество "Всероссийский научно-исследовательский институт по переработке нефти" | Способ получения антиокислительной присадки к смазочным маслам |
| JP5509484B2 (ja) * | 2007-06-08 | 2014-06-04 | インフィニューム インターナショナル リミテッド | 添加剤及びそれを含む潤滑油組成物 |
| EP2173803A1 (en) * | 2007-08-01 | 2010-04-14 | Basf Se | Liquid antioxidant mixtures |
| CN101863774B (zh) * | 2010-06-02 | 2014-06-04 | 江苏科技大学 | 离子液体催化制备液体烷基化二苯胺混合物的方法 |
| CN102701997A (zh) * | 2012-07-09 | 2012-10-03 | 江苏飞亚化学工业有限责任公司 | 一种二烷基二苯胺的提纯工艺 |
| US20160152789A1 (en) * | 2013-07-11 | 2016-06-02 | Nok Corporation | Nitrile rubber composition |
| CN103408431B (zh) * | 2013-08-20 | 2016-01-06 | 天津利安隆新材料股份有限公司 | 液态芳香胺类抗氧剂5057的制备方法 |
| US9617201B2 (en) | 2013-10-14 | 2017-04-11 | Chemtura Corporation | Fixed bed process for clay catalyzed alkylation of aromatic amines |
| US9744531B2 (en) | 2015-03-03 | 2017-08-29 | Lanxess Solutions Us Inc. | Regeneration of clay catalysts for alkylation of aromatic rings |
| CN105503617B (zh) * | 2015-07-30 | 2018-05-22 | 中国科学院宁波材料技术与工程研究所 | 高选择性烷基化二苯胺、其制备方法及应用 |
| GB2579405B (en) | 2018-11-30 | 2022-09-14 | Si Group Switzerland Chaa Gmbh | Antioxidant compositions |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2943112A (en) * | 1957-11-06 | 1960-06-28 | Pennsalt Chemicals Corp | Alkylation of diphenylamine |
| US3505225A (en) * | 1966-04-07 | 1970-04-07 | Uniroyal Inc | Derivatives of diphenylamine and the phenylnaphthylamines as antioxidants and as synergists with dialkyl 3,3'-thiodipropionates |
| GB1236740A (en) * | 1969-04-11 | 1971-06-23 | Geigy Uk Ltd | Tertiary alkylated diphenylamines and their uses as antioxidants |
| GB8332797D0 (en) * | 1983-12-08 | 1984-01-18 | Ciba Geigy Ag | Antioxidant production |
| JPS60202845A (ja) * | 1984-03-28 | 1985-10-14 | Seikou Kagaku Kk | 白度または透明度の高いｐ−置換ジフエニルアミン類の製造法 |
| KR0173792B1 (ko) * | 1990-09-13 | 1999-03-20 | 월터콜리웨인; 한스-피터 위트린 | 페노티아진을 함유하는 혼합물 및 조성물 |
| US5214211A (en) * | 1991-12-12 | 1993-05-25 | Uop | Alkylation of diarylamines with olefins using rare earth modified pillared clays |
| US5321159A (en) * | 1992-12-18 | 1994-06-14 | The B. F. Goodrich Company | Decolorization of alkylated diarylamines |
-
1996
- 1996-05-30 US US08/655,511 patent/US5750787A/en not_active Expired - Fee Related
-
1997
- 1997-05-29 CA CA002206429A patent/CA2206429C/en not_active Expired - Fee Related
- 1997-05-30 AT AT04001128T patent/ATE376990T1/de not_active IP Right Cessation
- 1997-05-30 AT AT00106387T patent/ATE258159T1/de not_active IP Right Cessation
- 1997-05-30 DE DE69727323T patent/DE69727323T2/de not_active Expired - Fee Related
- 1997-05-30 EP EP04001128A patent/EP1411044B1/en not_active Expired - Lifetime
- 1997-05-30 DE DE69710638T patent/DE69710638T2/de not_active Expired - Fee Related
- 1997-05-30 JP JP14217197A patent/JP4116114B2/ja not_active Expired - Fee Related
- 1997-05-30 EP EP00106387A patent/EP1020425B1/en not_active Expired - Lifetime
- 1997-05-30 EP EP97108664A patent/EP0810200B1/en not_active Expired - Lifetime
- 1997-05-30 DE DE69738259T patent/DE69738259T2/de not_active Expired - Fee Related
- 1997-05-30 AT AT97108664T patent/ATE213723T1/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE69710638T2 (de) | 2002-10-17 |
| DE69738259D1 (de) | 2007-12-13 |
| HK1029579A1 (en) | 2001-04-06 |
| CA2206429C (en) | 2006-02-21 |
| DE69710638D1 (de) | 2002-04-04 |
| EP1020425A2 (en) | 2000-07-19 |
| ATE213723T1 (de) | 2002-03-15 |
| ATE258159T1 (de) | 2004-02-15 |
| ATE376990T1 (de) | 2007-11-15 |
| JP4116114B2 (ja) | 2008-07-09 |
| HK1065529A1 (en) | 2005-02-25 |
| EP0810200B1 (en) | 2002-02-27 |
| DE69727323D1 (de) | 2004-02-26 |
| JPH1081652A (ja) | 1998-03-31 |
| DE69727323T2 (de) | 2004-10-21 |
| EP1411044A1 (en) | 2004-04-21 |
| US5750787A (en) | 1998-05-12 |
| CA2206429A1 (en) | 1997-11-30 |
| EP0810200A2 (en) | 1997-12-03 |
| EP1020425A3 (en) | 2001-02-14 |
| EP0810200A3 (en) | 1999-01-20 |
| EP1020425B1 (en) | 2004-01-21 |
| EP1411044B1 (en) | 2007-10-31 |
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| 8364 | No opposition during term of opposition | ||
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