UA83398C2 - Антиокислительная композиция на основе дифениламина и способ ее получения - Google Patents
Антиокислительная композиция на основе дифениламина и способ ее получения Download PDFInfo
- Publication number
- UA83398C2 UA83398C2 UAA200606989A UAA200606989A UA83398C2 UA 83398 C2 UA83398 C2 UA 83398C2 UA A200606989 A UAA200606989 A UA A200606989A UA A200606989 A UAA200606989 A UA A200606989A UA 83398 C2 UA83398 C2 UA 83398C2
- Authority
- UA
- Ukraine
- Prior art keywords
- aza
- iai
- aasz
- aya
- oei
- Prior art date
Links
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 title abstract description 13
- 239000000203 mixture Substances 0.000 title abstract description 4
- 239000003963 antioxidant agent Substances 0.000 title abstract description 3
- 230000003078 antioxidant effect Effects 0.000 title abstract description 3
- BIHPYCDDPGNWQO-UHFFFAOYSA-N 5-iai Chemical compound C1=C(I)C=C2CC(N)CC2=C1 BIHPYCDDPGNWQO-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 abstract description 2
- 239000000126 substance Substances 0.000 abstract description 2
- FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical group CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 230000029936 alkylation Effects 0.000 abstract 1
- 238000005804 alkylation reaction Methods 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000006731 degradation reaction Methods 0.000 abstract 1
- 239000000314 lubricant Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 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 abstract 1
- 239000003921 oil Substances 0.000 abstract 1
- 239000003381 stabilizer Substances 0.000 abstract 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000032683 aging Effects 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- POXUQBFHDHCZAD-MHTLYPKNSA-N (2r)-2-[(4s)-2,2-dimethyl-1,3-dioxolan-4-yl]-3,4-dihydroxy-2h-furan-5-one Chemical compound O1C(C)(C)OC[C@H]1[C@@H]1C(O)=C(O)C(=O)O1 POXUQBFHDHCZAD-MHTLYPKNSA-N 0.000 description 1
- 241000223477 Abea Species 0.000 description 1
- VTXJIDBQMAXDIY-QKBMRJQYSA-N C[C@H]1CN[C@]2(C[C@H]3O[C@]4(CC(=C)[C@H]5O[C@@](O)([C@H](O)[C@@H]6C[C@H]7O[C@@]8(CC[C@]9(CC=C[C@H](O9)\C=C\CCC(O)=O)O8)[C@H](C)C[C@H]7O6)[C@H](C)[C@H](O)[C@@H]5C)C[C@@H](C)C[C@@H](O4)[C@H]3O2)[C@@H](C)C1 Chemical compound C[C@H]1CN[C@]2(C[C@H]3O[C@]4(CC(=C)[C@H]5O[C@@](O)([C@H](O)[C@@H]6C[C@H]7O[C@@]8(CC[C@]9(CC=C[C@H](O9)\C=C\CCC(O)=O)O8)[C@H](C)C[C@H]7O6)[C@H](C)[C@H](O)[C@@H]5C)C[C@@H](C)C[C@@H](O4)[C@H]3O2)[C@@H](C)C1 VTXJIDBQMAXDIY-QKBMRJQYSA-N 0.000 description 1
- 241000435574 Popa Species 0.000 description 1
- 229940106943 azor Drugs 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000035882 stress Effects 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
- C08K5/18—Amines; Quaternary ammonium compounds with aromatically bound amino groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K2201/00—Specific properties of additives
- C08K2201/014—Additives containing two or more different additives of the same subgroup in C08K
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Lubricants (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Способ получения антиокислительной композиции на основе дифениламина каталитическим алкилированием дифениламина трехкратным избытком диизобутилена относительно дифениламина в присутствии алкилирующего катализатора в количестве от 5 до 30 масс. % по отношению к дифениламину, при температуре от 140 до 160 °С. Воду, которая содержится в катализаторе, удаляют, и потом дифениламин оставляют для завершения реакции с диизобутиленом, и после окончания реакции реакционную смесь отделяют от катализатора, диизобутилен, который не прореагировал, удаляют из нее и получают продукт реакции.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
SK1456-2003A SK14562003A3 (sk) | 2003-11-25 | 2003-11-25 | Antioxidačné kompozície oktylovaných difenylamínov a spôsob ich výroby |
PCT/SK2004/000013 WO2005052050A1 (en) | 2003-11-25 | 2004-11-25 | Antioxidant compositions of octylated diphenylamines and method of their preparation |
Publications (1)
Publication Number | Publication Date |
---|---|
UA83398C2 true UA83398C2 (ru) | 2008-07-10 |
Family
ID=34632267
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
UAA200606989A UA83398C2 (ru) | 2003-11-25 | 2004-11-25 | Антиокислительная композиция на основе дифениламина и способ ее получения |
Country Status (14)
Country | Link |
---|---|
US (1) | US7928265B2 (ru) |
EP (1) | EP1694757B1 (ru) |
JP (1) | JP2007512409A (ru) |
KR (1) | KR20060135638A (ru) |
CN (1) | CN1882651B (ru) |
AT (1) | ATE382654T1 (ru) |
CA (1) | CA2545561A1 (ru) |
DE (1) | DE602004011106T2 (ru) |
ES (1) | ES2298842T3 (ru) |
PL (1) | PL1694757T3 (ru) |
RU (1) | RU2382798C2 (ru) |
SK (1) | SK14562003A3 (ru) |
UA (1) | UA83398C2 (ru) |
WO (1) | WO2005052050A1 (ru) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101348720B (zh) * | 2007-07-18 | 2012-07-18 | 中国石油化工股份有限公司 | 复合胺类抗氧剂及其制备方法和应用 |
WO2010017030A1 (en) * | 2008-08-08 | 2010-02-11 | Albemarle Corporation | Octylated phenyl-alpha-naphthylamine product mixtures and production of such mixtures having a high content of octylated phenyl-alpha-naphthylamine |
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 |
US9890346B2 (en) | 2014-07-21 | 2018-02-13 | Lanxess Solutions Us Inc. | Selective alkylation method for producing p, p′-di-alkylated diphenylamine antioxidants |
CN106552626B (zh) * | 2015-09-29 | 2019-06-04 | 中国石油化工集团公司 | SiO2为主要载体的催化剂在合成橡胶防老剂6PPD中的应用 |
Family Cites Families (25)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2776994A (en) * | 1954-03-03 | 1957-01-08 | Goodrich Co B F | Preparation of a solid diphenylamine antioxidant |
US2943112A (en) | 1957-11-06 | 1960-06-28 | Pennsalt Chemicals Corp | Alkylation of diphenylamine |
NL241551A (ru) * | 1958-08-01 | |||
US3414618A (en) | 1964-02-11 | 1968-12-03 | Geigy Co Ltd The | Mono-p-tertiary alkyl diarylamines |
US3496230A (en) * | 1966-02-17 | 1970-02-17 | American Cyanamid Co | Process for mixture of mono- and dialkyl-diphenylamines |
US3714258A (en) * | 1970-08-28 | 1973-01-30 | Reichhold Chemicals Inc | Dialkylated diarylamines and a method for producing same |
SU443016A1 (ru) | 1972-06-19 | 1974-09-15 | Украинский научно-исследовательский углехимический институт | Способ получени мезитилена |
US4146687A (en) * | 1977-08-22 | 1979-03-27 | Stauffer Chemical Company | Flame retarded polyurethane foams with improved color characteristics |
CA1106409A (en) | 1977-10-07 | 1981-08-04 | Richard M. D'sidocky | Base modified catalysis in the styrenation of diphenylamine |
JPS5468898A (en) * | 1977-11-11 | 1979-06-02 | Bridgestone Corp | Low-density non-rigid urethane foam and its manufacture |
CS226248B1 (cs) | 1982-06-18 | 1984-03-19 | Cvengrosova Zuzana | Esterový olej so zvýšenou oxidačne-termickou stabilitou |
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 |
CS261085B1 (cs) | 1987-01-20 | 1989-01-12 | Tibor Goegh | Zmesný termický a termooxidačný stabilizátor a sposob jeho přípravy |
US4837259A (en) | 1987-09-25 | 1989-06-06 | Uniroyal Chemical Company, Inc. | Polypropylene stabilized against oxidative degradation with mixtures of diarylamine derivatives and sterically hindered phenols |
ZA887069B (en) * | 1987-09-25 | 1989-05-30 | Uniroyal Chem Co Inc | Polypropylene stabilized against oxidative degradation with mixtures of diarylemine derivatives and sterically hindered phenols |
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 |
TW300246B (ru) * | 1995-04-11 | 1997-03-11 | Mitsui Petroleum Chemicals Ind | |
US5672752A (en) | 1995-09-13 | 1997-09-30 | The Bfgoodrich Company | Liquid alkylated diphenylamine antioxidant |
US5750787A (en) * | 1995-09-13 | 1998-05-12 | B. F. Goodrich Company | Liquid alkylated diphenylamine antioxidant |
JPH10298148A (ja) * | 1997-04-23 | 1998-11-10 | Seiko Kagaku Kk | ブチル化ジフェニルアミン類の製造方法 |
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 |
US6816655B2 (en) * | 2001-10-31 | 2004-11-09 | Ciba Specialty Chemicals Corporation | Copper and optical fiber cable with improved filling material |
-
2003
- 2003-11-25 SK SK1456-2003A patent/SK14562003A3/sk unknown
-
2004
- 2004-11-25 ES ES04800460T patent/ES2298842T3/es active Active
- 2004-11-25 KR KR1020067010217A patent/KR20060135638A/ko not_active Application Discontinuation
- 2004-11-25 RU RU2006122520/04A patent/RU2382798C2/ru not_active IP Right Cessation
- 2004-11-25 CA CA002545561A patent/CA2545561A1/en not_active Abandoned
- 2004-11-25 UA UAA200606989A patent/UA83398C2/ru unknown
- 2004-11-25 AT AT04800460T patent/ATE382654T1/de not_active IP Right Cessation
- 2004-11-25 WO PCT/SK2004/000013 patent/WO2005052050A1/en active IP Right Grant
- 2004-11-25 CN CN2004800345105A patent/CN1882651B/zh not_active Expired - Fee Related
- 2004-11-25 EP EP04800460A patent/EP1694757B1/en not_active Not-in-force
- 2004-11-25 JP JP2006541105A patent/JP2007512409A/ja active Pending
- 2004-11-25 DE DE602004011106T patent/DE602004011106T2/de active Active
- 2004-11-25 PL PL04800460T patent/PL1694757T3/pl unknown
-
2006
- 2006-05-05 US US11/418,785 patent/US7928265B2/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
ES2298842T3 (es) | 2008-05-16 |
JP2007512409A (ja) | 2007-05-17 |
US20060205981A1 (en) | 2006-09-14 |
KR20060135638A (ko) | 2006-12-29 |
DE602004011106D1 (de) | 2008-02-14 |
CN1882651B (zh) | 2011-07-06 |
EP1694757B1 (en) | 2008-01-02 |
ATE382654T1 (de) | 2008-01-15 |
CA2545561A1 (en) | 2005-06-09 |
DE602004011106T2 (de) | 2009-02-05 |
RU2382798C2 (ru) | 2010-02-27 |
EP1694757A1 (en) | 2006-08-30 |
US7928265B2 (en) | 2011-04-19 |
SK14562003A3 (sk) | 2005-06-02 |
RU2006122520A (ru) | 2008-01-10 |
WO2005052050A1 (en) | 2005-06-09 |
PL1694757T3 (pl) | 2008-07-31 |
CN1882651A (zh) | 2006-12-20 |
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