CN101778893B - 液体抗氧化剂混合物 - Google Patents
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Abstract
本发明提供了辛基化/丁基化二苯胺、吩噻嗪和(3,5-二叔丁基-4-羟苯基)丙酸十八烷基酯的液体抗氧化剂混合物。该抗氧化剂混合物用于聚氨酯的稳定化。
Description
本发明目的在于一种用于塑料的特定抗氧化添加剂的液体混合物。该抗氧化剂是辛基化/丁基化二苯胺、吩噻嗪和(3,5-二叔丁基-4-羟苯基)丙酸十八烷基酯。该液体抗氧化剂混合物用于聚氨酯的稳定化。
辛基化/丁基化二苯胺是一种用于各种有机材料的已知抗氧化剂。例如在美国4,824,601中教导的。
吩噻嗪是一种用于有机材料的已知抗氧化剂。
(3,5-二叔丁基-4-羟苯基)丙酸十八烷基酯是一种熟知的用于有机材料的酚类抗氧化剂。例如在美国4,228,297中公开的。
抗氧化剂包的液体混合物对于塑料制造是理想的。辛基化/丁基化二苯胺和吩噻嗪的双组分混合物在环境条件之下是不稳定的液体。令人惊讶地,已经发现加入少量另外的抗氧化剂(3,5-二叔丁基-4-羟苯基)丙酸十八烷基酯使得该混合物在特定温度下为液体。
公开的是一种包含辛基化/丁基化二苯胺、吩噻嗪和(3,5-二叔丁基-4-羟苯基)丙酸十八烷基酯的液体抗氧化剂混合物。
还公开了一种用于提供液体抗氧化剂混合物的方法,所述方法包含向辛基化/丁基化二苯胺和吩噻嗪的双组分混合物中加入(3,5-二叔丁基-4-羟苯基)丙酸十八烷基酯并且搅拌和任选地加热该混合物。
辛基化/丁基化二苯胺的制备公开于例如美国专利号4,824,601中。它是二苯胺与二异丁烯(2,4,4-三甲基戊烯)的反应产物。其结构是:
其中,R和R1独立地是H、C4H9或C8H17。这种化合物混合物在室温下是液体。
吩噻嗪可商购获得,例如购自Sigma-Aldrich。它是:
吩噻嗪具有182-187℃的熔点。
(3,5-二叔丁基-4-羟苯基)丙酸十八烷基酯是:
(3,5-二叔丁基-4-羟苯基)丙酸十八烷基酯的制备公开于例如美国4,228,297中。(3,5-二叔丁基-4-羟苯基)丙酸十八烷基酯具有50-55℃的熔点。
该三部分抗氧化剂混合物在例如环境温度和压力下是液体。该混合物在例如约25℃至约60℃在环境压力下是液体。该混合物在例如约40℃至约60℃在环境压力下是液体。
环境条件是约25℃和约1大气压。
公开了一种液体抗氧化剂混合物,其包含74.4-79.0重量%的辛基化/丁基化二苯胺,3.0-3.6重量%的吩噻嗪和18.0-22.0重量%的(3,5-二叔丁基-4-羟苯基)丙酸十八烷基酯,其中抗氧化剂的总重量是100%。这种液体混合物在40℃下是稳定的。
该液体抗氧化剂混合物特别地包含76.7重量%的辛基化/丁基化二苯胺,3.3重量%的吩噻嗪和20.0重量%的(3,5-二叔丁基-4-羟苯基)丙酸十八烷基酯。
还公开了一种液体抗氧化剂混合物,其包含84.8-87.5重量%的辛基化/丁基化二苯胺,3.4-4.1重量%的吩噻嗪和9.1-11.1重量%的(3,5-二叔丁基-4-羟苯基)丙酸十八烷基酯,其中抗氧化剂的总重量是100%。这种液体混合物在60℃下是稳定的。
该液体抗氧化剂混合物特别地包含86.2重量%的辛基化/丁基化二苯胺,3.8重量%的吩噻嗪和10.0重量%的(3,5-二叔丁基-4-羟苯基)丙酸十八烷基酯。
还公开了一种液体抗氧化剂混合物,包含89.2-91.2重量%的辛基化/丁基化二苯胺,3.5-4.3重量%的吩噻嗪和5.3-6.5重量%的(3,5-二叔丁基-4-羟苯基)丙酸十八烷基酯,其中抗氧化剂的总重量是100%。这种液体混合物在60℃下是稳定的。
该液体抗氧化剂混合物特别地包含90.3重量%的辛基化/丁基化二苯胺,3.9重量%的吩噻嗪和5.8重量%的(3,5-二叔丁基-4-羟苯基)丙酸十八烷基酯。
本发明还涉及用于使聚氨酯或其前体稳定以抗氧化、热或光诱发降解的方法,其包括向聚氨酯或其前体中引入或向其施加上述的液体抗氧化剂混合物。
本发明另一个实施方式涉及上述液体抗氧化剂混合物用于使聚氨酯或其前驱体稳定以抗氧化、热或光诱发降解的用途。
优选将液体抗氧化剂混合以0.0005-10%,优选0.001-2%,典型地0.01-2%的浓度加入到要稳定的聚氨酯中,基于聚氨酯的重量。
液体抗氧化剂混合物同样用于聚氨酯生产,尤其用于制备柔性聚氨酯泡沫。在上下文中,液体抗氧化剂混合物保护产物不受降解。特别地,避免在泡沫制造过程中的焦烧。
聚氨酯从前体获得,例如通过将含有末端羟基基团的聚醚、聚酯和聚丁二烯与脂族或芳族多异氰酸酯反应。
具有末端羟基基团的聚醚是已知的,并且例如如下所述制备:通过使环氧化物如环氧乙烷、环氧丙烷、环氧丁烷、四氢呋喃、氧化苯乙烯或表氯醇与它们自身,例如在BF3的存在下聚合,或通过这些环氧化物单独或作为混合物或依次地与含有反应性氢原子的起始组分如水、醇、氨或胺,例如乙二醇、1,3-丙二醇和1,2-丙二醇、三羟甲基丙烷、4,4′-二羟基二苯基丙烷、苯胺、乙醇胺或乙二胺的加成反应。根据本发明,蔗糖聚醚也是合适的。在许多情形中优选那些主要(基于存在于聚醚之中的全部OH基团,多达90重量%)含有伯OH基团的聚醚。此外,例如通过在聚醚存在下聚合苯乙烯和丙烯腈形成的乙烯基聚合物改性的聚醚是合适的,例如含有OH基团的聚丁二烯。
这些化合物一般具有400-10000的分子量并且是多羟基化合物,尤其是含有2-8个羟基基团的化合物,尤其是分子量为800-10000,优选1000-6000的那些,例如含有至少2个、一般2-8个、优选2-4个羟基基团的聚醚,例如已知用于制备均相聚氨酯和细胞状聚氨酯的那些。
当然可以使用上述含有至少两个异氰酸酯-反应性氢原子,特别是分子量400-10000的化合物的混合物。
合适的多异氰酸酯为脂族、脂环族、芳脂族、芳族和杂环多异氰酸酯,例如亚乙基二异氰酸酯、1,4-四亚甲基二异氰酸酯、1,6-六亚甲基二异氰酸酯、1,12-十二烷二异氰酸酯、环丁烷1,3二异氰酸酯、环己烷1,3-和1,4-二异氰酸酯以及这些异构体的任何希望的混合物、1-异氰酸根合-3,3,5-三甲基-5-异氰酸根合甲基环己烷、2,4-和2,6-六氢甲苯二异氰酸酯以及这些异构体的任何希望的混合物、六氢-1,3-和/或1,4-苯二异氰酸酯、全氢-2,4′-和/或-4,4′-二苯基甲烷二异氰酸酯、1,3-和1,4-苯二异氰酸酯、2,4-和2,6-甲苯二异氰酸酯以及这些异构体的任何希望的混合物、二苯基甲烷2,4′-和/或4,4′二异氰酸酯、萘1,5-二异氰酸酯、三苯甲烷4,4′,4″-三异氰酸酯、通过苯胺-甲醛缩合随后光气化获得的多苯基多亚甲基多异氰酸酯、间和对异氰酸根合苯基磺酰基异氰酸酯、全氯化芳基多异氰酸酯、含碳二亚胺基团的多异氰酸酯、含脲基甲酸酯基的多异氰酸酯、含异氰脲酸酯基的多异氰酸酯、含尿烷基的多异氰酸酯、含酰化脲基的多异氰酸酯、含缩二脲基的多异氰酸酯、含酯基的多异氰酸酯、上述异氰酸酯与乙缩醛的反应产物和含聚合物脂肪酸基团的多异氰酸酯。
可以使用含异氰酸酯基的蒸馏残渣,以它们本身的形式或者溶解在一种或多种上述多异氰酸酯中,其在异氰酸酯的工业制备过程中获得。另外可以使用上述多异氰酸酯的任何希望的混合物。
一般地,特别优选工业上可容易获得的多异氰酸酯,例如2,4-和2,6-甲苯二异氰酸酯和这些异构体(“TDI”)的任何希望的混合物,通过苯胺-甲醛缩合随后光气化制备的多苯基-多亚甲基-多异氰酸酯(“粗制MDI”)、和含碳二亚胺、尿烷、脲基甲酸酯、异氰脲酸酯、脲或缩二脲基团的多异氰酸酯(“改性多异氰酸酯”)。
实施例:
配方1:115克辛基化/丁基化二苯胺
5克吩噻嗪
30克(3,5-二叔丁基-4-羟苯基)丙酸十八烷基酯
在加热下搅拌混合物。所得的液体在40℃下是稳定的。
配方2:115克的辛基化/丁基化二苯胺
5克的吩噻嗪
13.5克的(3,5-二叔丁基-4-羟苯基)丙酸十八烷基酯
在加热下搅拌混合物。所得的液体在60℃下是稳定的。
配方3:115克的辛基化的/丁基化二苯胺
5克的吩噻嗪
7.5克的(3,5-二叔丁基-4-羟苯基)丙酸十八烷基酯
在加热下搅拌混合物。所得的液体在60℃下是稳定的。
术语“稳定”是指液体在规定温度下在至少4天的时期内保持液态。液体受到震动时不结晶。
使用布氏粘度计,锭子31测量配方1的粘度。
Claims (9)
1.一种液体抗氧化剂混合物,包含74.4-79.0重量%的辛基化/丁基化二苯胺、3.0-3.6重量%的吩噻嗪和18.0-22.0重量%(3,5-二叔丁基-4-羟苯基)丙酸十八烷基酯,其中抗氧化剂的总重量为100%,所述辛基化/丁基化二苯胺具有如下结构:
其中R和R1独立地是H、C4H9或C8H17。
2.根据权利要求1的液体混合物,包含76.7重量%的辛基化/丁基化二苯胺、3.3重量%的吩噻嗪和20.0重量%的(3,5-二叔丁基-4-羟苯基)丙酸十八烷基酯。
3.根据权利要求1的液体混合物,其在40℃下是稳定的。
4.一种液体抗氧化剂混合物,包含84.8-87.5重量%的辛基化/丁基化二苯胺、3.4-4.1重量%的吩噻嗪和9.1-11.1重量%的(3,5-二叔丁基-4-羟苯基)丙酸十八烷基酯,其中抗氧化剂的总重量为100%,所述辛基化/丁基化二苯胺具有如下结构:
其中R和R1独立地是H、C4H9或C8H17。
5.根据权利要求4的液体抗氧化剂混合物,包含86.2重量%的辛基化/丁基化二苯胺、3.8重量%的吩噻嗪和10.0重量%的(3,5-二叔丁基-4-羟苯基)丙酸十八烷基酯。
6.根据权利要求4的液体抗氧化剂混合物,其在60℃下是稳定的。
8.根据权利要求7的液体抗氧化剂混合物,包含90.3重量%的辛基化/丁基化二苯胺、3.9重量%的吩噻嗪和5.8重量%的(3,5-二叔丁基-4-羟苯基)丙酸十八烷基酯。
9.根据权利要求7的液体抗氧化剂混合物,其在60℃下是稳定的。
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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 |
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EP (1) | EP2173803A1 (zh) |
JP (1) | JP2010534754A (zh) |
CN (1) | CN101778893B (zh) |
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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 |
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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 |
CN1290910C (zh) * | 2002-03-21 | 2006-12-20 | 西巴特殊化学品控股有限公司 | 用于抗氧化剂的水分散体 |
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 |
KR100704807B1 (ko) * | 2003-03-17 | 2007-04-09 | 아사히 가세이 케미칼즈 가부시키가이샤 | 폴리트리메틸렌 테레프탈레이트 조성물과 그의 제조 방법 |
DE10324998A1 (de) * | 2003-06-03 | 2004-12-23 | Basf Ag | Herstellung von Polyetheralkoholen unter Verwendung der DMC-Katalyse |
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US20070185250A1 (en) * | 2003-12-04 | 2007-08-09 | Ciba Specialty Chemicals Holding Inc. | Stabilization of polyether polyols, polyester polyols and polyurethanes |
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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 |
EP1874853B2 (en) * | 2005-04-19 | 2012-07-04 | Basf Se | Polyether polyols, polyester polyols and polyurethanes of low residual aldehyde content |
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- 2008-07-23 JP JP2010518620A patent/JP2010534754A/ja not_active Ceased
- 2008-07-23 CN CN2008801010840A patent/CN101778893B/zh not_active Expired - Fee Related
- 2008-07-23 WO PCT/EP2008/059624 patent/WO2009016073A1/en active Application Filing
- 2008-07-30 TW TW097128730A patent/TW200920781A/zh unknown
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CN101778893A (zh) | 2010-07-14 |
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