CN101778893B - 液体抗氧化剂混合物 - Google Patents
液体抗氧化剂混合物 Download PDFInfo
- Publication number
- CN101778893B CN101778893B CN2008801010840A CN200880101084A CN101778893B CN 101778893 B CN101778893 B CN 101778893B CN 2008801010840 A CN2008801010840 A CN 2008801010840A CN 200880101084 A CN200880101084 A CN 200880101084A CN 101778893 B CN101778893 B CN 101778893B
- Authority
- CN
- China
- Prior art keywords
- weight
- liquid
- butyl
- phenylor
- thiodiphenylamine
- 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
- 239000000203 mixture Substances 0.000 title claims abstract description 48
- 239000007788 liquid Substances 0.000 title claims abstract description 43
- 239000003963 antioxidant agent Substances 0.000 title claims abstract description 32
- 230000003078 antioxidant effect Effects 0.000 title claims abstract description 30
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims abstract description 23
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 46
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N pentanoic acid group Chemical group C(CCCC)(=O)O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 25
- 230000006208 butylation Effects 0.000 claims description 24
- 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 claims description 24
- 235000019260 propionic acid Nutrition 0.000 claims description 23
- 239000003112 inhibitor Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000004814 polyurethane Substances 0.000 abstract description 3
- 229920002635 polyurethane Polymers 0.000 abstract description 3
- 230000006641 stabilisation Effects 0.000 abstract description 2
- 238000011105 stabilization Methods 0.000 abstract description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 abstract 1
- XHLCCKLLXUAKCM-UHFFFAOYSA-N octadecyl 2-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 XHLCCKLLXUAKCM-UHFFFAOYSA-N 0.000 abstract 1
- 229950000688 phenothiazine Drugs 0.000 abstract 1
- 235000006708 antioxidants Nutrition 0.000 description 22
- 229920000538 Poly[(phenyl isocyanate)-co-formaldehyde] Polymers 0.000 description 16
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 10
- 229920000570 polyether Polymers 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- -1 oxyethane Chemical class 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 229920001228 polyisocyanate Polymers 0.000 description 3
- 239000005056 polyisocyanate Substances 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 230000006353 environmental stress Effects 0.000 description 2
- DYDNPESBYVVLBO-UHFFFAOYSA-N formanilide Chemical compound O=CNC1=CC=CC=C1 DYDNPESBYVVLBO-UHFFFAOYSA-N 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Natural products OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 150000002924 oxiranes Chemical class 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- WOGVOIWHWZWYOZ-UHFFFAOYSA-N 1,1-diisocyanatoethane Chemical compound O=C=NC(C)N=C=O WOGVOIWHWZWYOZ-UHFFFAOYSA-N 0.000 description 1
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 1
- LCVCUJWKJNFDMY-UHFFFAOYSA-N 2,2-diphenylpropane-1,1-diol Chemical compound C=1C=CC=CC=1C(C(O)O)(C)C1=CC=CC=C1 LCVCUJWKJNFDMY-UHFFFAOYSA-N 0.000 description 1
- FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical group CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 description 1
- UXFQFBNBSPQBJW-UHFFFAOYSA-N 2-amino-2-methylpropane-1,3-diol Chemical compound OCC(N)(C)CO UXFQFBNBSPQBJW-UHFFFAOYSA-N 0.000 description 1
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- KGWDUNBJIMUFAP-KVVVOXFISA-N Ethanolamine Oleate Chemical compound NCCO.CCCCCCCC\C=C/CCCCCCCC(O)=O KGWDUNBJIMUFAP-KVVVOXFISA-N 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920005830 Polyurethane Foam Polymers 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- NSOXQYCFHDMMGV-UHFFFAOYSA-N Tetrakis(2-hydroxypropyl)ethylenediamine Chemical compound CC(O)CN(CC(C)O)CCN(CC(C)O)CC(C)O NSOXQYCFHDMMGV-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- VPKDCDLSJZCGKE-UHFFFAOYSA-N carbodiimide group Chemical group N=C=N VPKDCDLSJZCGKE-UHFFFAOYSA-N 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000005313 fatty acid group Chemical group 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- 239000011496 polyurethane foam Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 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
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/005—Stabilisers against oxidation, heat, light, ozone
-
- 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
- C08K5/04—Oxygen-containing compounds
- C08K5/13—Phenols; Phenolates
- C08K5/134—Phenols containing ester groups
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Polyurethanes Or Polyureas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US96283707P | 2007-08-01 | 2007-08-01 | |
| US60/962,837 | 2007-08-01 | ||
| PCT/EP2008/059624 WO2009016073A1 (en) | 2007-08-01 | 2008-07-23 | Liquid antioxidant mixtures |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101778893A CN101778893A (zh) | 2010-07-14 |
| CN101778893B true CN101778893B (zh) | 2012-11-28 |
Family
ID=39842065
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2008801010840A Expired - Fee Related CN101778893B (zh) | 2007-08-01 | 2008-07-23 | 液体抗氧化剂混合物 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US7824575B2 (enExample) |
| EP (1) | EP2173803A1 (enExample) |
| JP (1) | JP2010534754A (enExample) |
| CN (1) | CN101778893B (enExample) |
| TW (1) | TW200920781A (enExample) |
| WO (1) | WO2009016073A1 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101805458B (zh) * | 2010-04-07 | 2012-02-08 | 天津力生化工有限公司 | 乳液型复合抗氧剂的制备方法 |
| GB2523756B (en) * | 2014-03-03 | 2017-01-11 | Addivant Switzerland Gmbh | Antioxidant compositions |
| JP2017513993A (ja) * | 2014-04-24 | 2017-06-01 | コベストロ、ドイチュラント、アクチエンゲゼルシャフトＣｏｖｅｓｔｒｏ Ｄｅｕｔｓｃｈｌａｎｄ Ａｇ | ポリエーテルカーボネートポリオール系ポリウレタンフォーム |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4228297A (en) * | 1972-12-27 | 1980-10-14 | Ciba-Geigy Corporation | Process for the production of hydroxyalkylphenyl derivatives |
| US4207229A (en) * | 1976-07-30 | 1980-06-10 | Ciba-Geigy Corporation | Hindered phenyl phosphites |
| US4233208A (en) * | 1978-07-12 | 1980-11-11 | Ciba-Geigy Corporation | Polymer compositions stabilized with hindered phenyl secondary phosphites |
| US4444676A (en) * | 1983-04-01 | 1984-04-24 | Atlantic Richfield Company | Stabilized polyoxyalkylene polyether polyols and polyurethane foams prepared therefrom |
| GB8332797D0 (en) | 1983-12-08 | 1984-01-18 | Ciba Geigy Ag | Antioxidant production |
| KR0173792B1 (ko) * | 1990-09-13 | 1999-03-20 | 월터콜리웨인; 한스-피터 위트린 | 페노티아진을 함유하는 혼합물 및 조성물 |
| US5219892A (en) * | 1992-06-16 | 1993-06-15 | R. T. Vanderbilt Company, Inc. | Liquid stabilizer compositions for polyols and polyurethane foam |
| US5256333A (en) * | 1993-03-25 | 1993-10-26 | Uniroyal Chemical Company, Inc. | Stabilized polyether polyol and polyurethane foam obtained therefrom |
| US5750787A (en) * | 1995-09-13 | 1998-05-12 | B. F. Goodrich Company | Liquid alkylated diphenylamine antioxidant |
| DK1485441T4 (da) * | 2002-03-21 | 2009-11-23 | Basf Se | Vandige dispersioner for antioxidanter |
| JP2004143422A (ja) * | 2002-08-30 | 2004-05-20 | Sanyo Chem Ind Ltd | 軟質ポリウレタンフォームの製造方法 |
| DE112004000366B4 (de) * | 2003-03-17 | 2009-08-27 | Asahi Kasei Chemicals Corp. | Polytrimethylenterephthalat-Zusammensetzung |
| DE10324998A1 (de) * | 2003-06-03 | 2004-12-23 | Basf Ag | Herstellung von Polyetheralkoholen unter Verwendung der DMC-Katalyse |
| DE10344448A1 (de) * | 2003-09-25 | 2005-04-28 | Henkel Kgaa | Bindemittel mit Barriere-Eigenschaft |
| CN1890284A (zh) | 2003-12-04 | 2007-01-03 | 西巴特殊化学品控股有限公司 | 聚醚多元醇、聚酯多元醇和聚氨酯的稳定 |
| CA2575502C (en) * | 2004-08-18 | 2013-06-04 | Ciba Specialty Chemicals Holding Inc. | Lubricating oil compositions comprising phenolic antioxidant |
| JP4797413B2 (ja) * | 2005-03-22 | 2011-10-19 | 東ソー株式会社 | クロロプレンゴム及びその製造方法 |
| WO2006111492A2 (en) * | 2005-04-19 | 2006-10-26 | Ciba Specialty Chemicals Holding Inc. | Polyether polyols, polyester polyols and polyurethanes of low residual aldehyde content |
-
2008
- 2008-07-23 EP EP08775294A patent/EP2173803A1/en not_active Withdrawn
- 2008-07-23 JP JP2010518620A patent/JP2010534754A/ja not_active Ceased
- 2008-07-23 WO PCT/EP2008/059624 patent/WO2009016073A1/en not_active Ceased
- 2008-07-23 CN CN2008801010840A patent/CN101778893B/zh not_active Expired - Fee Related
- 2008-07-30 TW TW097128730A patent/TW200920781A/zh unknown
- 2008-07-31 US US12/221,114 patent/US7824575B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US7824575B2 (en) | 2010-11-02 |
| JP2010534754A (ja) | 2010-11-11 |
| TW200920781A (en) | 2009-05-16 |
| CN101778893A (zh) | 2010-07-14 |
| EP2173803A1 (en) | 2010-04-14 |
| US20090032769A1 (en) | 2009-02-05 |
| WO2009016073A1 (en) | 2009-02-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| C17 | Cessation of patent right | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20121128 Termination date: 20130723 |