CN104114628B - 液体稳定剂混合物 - Google Patents
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Abstract
本发明涉及两种提供a)季戊四醇四(3-(3,5-二叔丁基-4-羟基苯基)丙酸酯，b)3-(3,5-二叔丁基-4-羟基苯基)丙酸十八烷基酯和c)亚磷酸三(2,4-二叔丁基苯基)酯的稳定液体共混物的方法。第一种方法包括制备包含约2-3重量份a)，约2-3重量份b)和约2-12重量份c)的固体混合物，将该混合物加热至185℃或更高并保持足够时间以获得a)、b)和c)的清澈液体共混物，将该液体共混物冷却至90-140℃的温度并将该液体共混物维持在90-140℃的温度下。第二种方法包括制备包含约2-3重量份a)和约2-3重量份b)的固体混合物，将该混合物加热至90℃或更高并保持足够时间以形成a)和b)的清澈液体混合物，将约2-12重量份c)加入其中以得到a)、b)和c)的清澈液体共混物并将该液体共混物维持在90-140℃的温度下。a)、b)和c)的液体共混物在它们所维持的温度下稳定大于120小时。
Description
本发明涉及提供a)季戊四醇四(3-(3,5-二叔丁基-4-羟基苯基)丙酸酯，b)3-(3,5-二叔丁基-4-羟基苯基)丙酸十八烷基酯和c)亚磷酸三(2,4-二叔丁基苯基)酯的稳定液体共混物的方法。稳定剂的液体共混物可以用作有机材料的稳定剂，例如用于合成聚合物稳定化。
季戊四醇四(3-(3,5-二叔丁基-4-羟基苯基)丙酸酯、3-(3,5-二叔丁基-4-羟基苯基)丙酸十八烷基酯和亚磷酸三(2,4-二叔丁基苯基)酯是众所周知的聚合物稳定剂，分别可以作为IRGANOX1010、IRGANOX1076和IRGAFOS168市购。IRGANOX1010和IRGANOX1076是受阻酚类抗氧化剂，而IRGAFOS168是亚磷酸酯类加工稳定剂。
季戊四醇四(3-(3,5-二叔丁基-4-羟基苯基)丙酸酯IRGANOX1010为：
3-(3,5-二叔丁基-4-羟基苯基)丙酸十八烷基酯IRGANOX1076为：
亚磷酸三(2,4-二叔丁基苯基)酯IRGAFOS168为：
这些稳定剂在室温下均为固体。IRGANOX1010的熔点为约120℃。IRGANOX1076的熔点为约56℃。IRGAFOS168在约185℃下熔融。
对工业可能有利的是能够提供这些众所周知的稳定剂的液体共混物。可以在熔体加工过程中或在溶液聚合过程中将液体共混物泵送而将其掺入聚合物中。投料将更准确且掺入更易进行。
现已发现两种形成a)季戊四醇四(3-(3,5-二叔丁基-4-羟基苯基)丙酸酯，b)3-(3,5-二叔丁基-4-羟基苯基)丙酸十八烷基酯和c)亚磷酸三(2,4-二叔丁基苯基)酯的稳定液体共混物的方法。
第一种方法
公开了一种形成a)季戊四醇四(3-(3,5-二叔丁基-4-羟基苯基)丙酸酯，b)3-(3,5-二叔丁基-4-羟基苯基)丙酸十八烷基酯和c)亚磷酸三(2,4-二叔丁基苯基)酯的稳定液体共混物的方法，该方法包括制备包含约2-3重量份a)，约2-3重量份b)和约2-12重量份c)的固体混合物，将该混合物加热至185℃或更高并保持足够时间以获得a)、b)和c)的清澈液体共混物，将该液体共混物冷却至90-140℃的温度并将该液体共混物维持在90-140℃的温度下，其中a)、b)和c)的液体共混物在它所维持的温度下稳定大于120小时。
优选该方法包括制备包含约5-11重量份c)的固体混合物。
更优选该方法包括制备包含约8-11重量份c)的固体混合物。
优选将a)、b)和c)的液体共混物维持在90-125℃的温度下。
更优选将a)、b)和c)的液体共混物维持在90-110℃的温度下。
第二种方法
进一步公开了一种形成a)季戊四醇四(3-(3,5-二叔丁基-4-羟基苯基)丙酸酯，b)3-(3,5-二叔丁基-4-羟基苯基)丙酸十八烷基酯和c)亚磷酸三(2,4-二叔丁基苯基)酯的稳定液体共混物的方法，该方法包括制备包含约2-3重量份a)和约2-3重量份b)的固体混合物，将该混合物加热至90℃或更高并保持足够时间以形成a)和b)的清澈液体混合物，将约2-12重量份c)加入其中以得到a)、b)和c)的清澈液体共混物并将该液体共混物维持在90-140℃的温度下，其中a)、b)和c)的液体共混物在它所维持的温度下稳定大于120小时。
优选该方法包括将约5-11重量份c)加入a)和b)的液体混合物中。
更优选该方法包括将约8-11重量份c)加入a)和b)的液体混合物中。
优选将a)、b)和c)的液体共混物维持在90-125℃的温度下。
更优选将a)、b)和c)的液体共混物维持在90-110℃的温度下。
冷却可以是快速冷却或者允许在环境条件下缓慢冷却。
稳定意味着在一定温度下在大于一定时间长度内没有观察到沉淀或固体。
实施例1
将10克IRGANOX1010/IRGANOX1076/IRGAFOS168样品干混并在200℃烘箱中的玻璃小瓶中放置半小时。得到清澈液体共混物。然后将清澈液体共混物转移到设置为150℃，140℃和135℃的烘箱中以观察在24、48、72、96和120小时的时间期间内在这些温度下是否出现任何沉淀。
在120小时下观察到下列结果：
配制剂3-5是非常稳定的液体共混物。更高含量的IRGANOX1010是有利的，即使其熔点比IRGANOX1076要高得多。
实施例2
重复实施例1，不同的是此时将含有IRGANOX1010和IRGANOX1076的混合物的玻璃小瓶置于油浴中并加热至大于90℃以得到清澈液体。在搅拌下将IRGAFOS168缓慢加入该液体中以得到清澈液体共混物。将液体共混物转移到设置在150℃，140℃和135℃下的烘箱中以观察在24、48、72、96和120小时的时间期间内在这些温度下是否出现任何沉淀。
Claims (10)
1.一种形成a)季戊四醇四(3-(3,5-二叔丁基-4-羟基苯基)丙酸酯，b)3-(3,5-二叔丁基-4-羟基苯基)丙酸十八烷基酯和c)亚磷酸三(2,4-二叔丁基苯基)酯的稳定液体共混物的方法，该方法包括制备包含2-3重量份a)，2-3重量份b)和2-12重量份c)的固体混合物，将所述混合物加热至185℃或更高并保持足够时间以获得a)、b)和c)的清澈液体共混物，将所述液体共混物冷却至90-140℃的温度并将所述液体共混物维持在90-140℃的温度下，其中a)、b)和c)的液体共混物在它所维持的温度下稳定大于120小时。
2.根据权利要求1的方法，包括制备包含5-11重量份c)的固体混合物。
3.根据权利要求1的方法，包括制备包含8-11重量份c)的固体混合物。
4.根据权利要求1的方法，其中将a)、b)和c)的液体共混物维持在90-125℃的温度下。
5.根据权利要求1的方法，其中将a)、b)和c)的液体共混物维持在90-110℃的温度下。
6.一种形成a)季戊四醇四(3-(3,5-二叔丁基-4-羟基苯基)丙酸酯，b)3-(3,5-二叔丁基-4-羟基苯基)丙酸十八烷基酯和c)亚磷酸三(2,4-二叔丁基苯基)酯的稳定液体共混物的方法，该方法包括制备包含2-3重量份a)和2-3重量份b)的固体混合物，将所述混合物加热至90℃或更高并保持足够时间以形成a)和b)的清澈液体混合物，将2-12重量份c)加入其中以得到a)、b)和c)的清澈液体共混物并将所述液体共混物维持在90-140℃的温度下，其中a)、b)和c)的液体共混物在它所维持的温度下稳定大于120小时。
7.根据权利要求6的方法，包括将5-11重量份c)加入a)和b)的液体混合物中。
8.根据权利要求6的方法，包括将8-11重量份c)加入a)和b)的液体混合物中。
9.根据权利要求6的方法，其中将a)、b)和c)的液体共混物维持在90-125℃的温度下。
10.根据权利要求6的方法，其中将a)、b)和c)的液体共混物维持在90-110℃的温度下。
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| CN1404498A (zh) * | 2000-02-21 | 2003-03-19 | 博里利斯技术公司 | 向聚合物颗粒中加入添加剂的方法 |
| CN101068868A (zh) * | 2003-12-04 | 2007-11-07 | 陶氏环球技术公司 | 稳定的聚乙烯材料 |
| CN101583639A (zh) * | 2006-10-11 | 2009-11-18 | 智利大学 | 用于制备纳米复合材料、微米复合材料和聚合物共混物的增容剂及其获得方法 |
| EP2163577A1 (en) * | 2008-09-15 | 2010-03-17 | Armacell Enterprise GmbH | Foamed thermoplastic cellular materials obtained by reactive extrusion process and with help of chain-extenders |
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| IT1231769B (it) * | 1989-08-02 | 1991-12-21 | Himont Inc | Procedimento per la stabilizzazione di poliolefine e prodotti da esso ottenuti. |
| GB0004044D0 (en) * | 2000-02-21 | 2000-04-12 | Borealis Polymers Oy | Polymer |
| JP3872999B2 (ja) * | 2002-04-04 | 2007-01-24 | 日本ポリプロ株式会社 | 塗膜黄変性に優れたポリプロピレン系樹脂組成物及びそれを用いた自動車外装部品 |
| TW200628530A (en) * | 2004-12-22 | 2006-08-16 | Clariant Int Ltd | Liquid or low melting stabilizr formulations |
| JP5369985B2 (ja) * | 2009-08-07 | 2013-12-18 | 東洋紡株式会社 | レトルト食品包装用フィルム |
| JP5680879B2 (ja) * | 2010-05-26 | 2015-03-04 | 株式会社Adeka | 樹脂添加剤マスターバッチ |
-
2012
- 2012-09-27 RU RU2014118603/04A patent/RU2600321C2/ru not_active IP Right Cessation
- 2012-09-27 SG SG11201401069TA patent/SG11201401069TA/en unknown
- 2012-09-27 KR KR1020147009357A patent/KR102013969B1/ko active IP Right Grant
- 2012-09-27 BR BR112014008472A patent/BR112014008472A2/pt active Search and Examination
- 2012-09-27 IN IN2605CHN2014 patent/IN2014CN02605A/en unknown
- 2012-09-27 EP EP12840357.3A patent/EP2766419B1/en not_active Not-in-force
- 2012-09-27 JP JP2014535734A patent/JP6045001B2/ja not_active Expired - Fee Related
- 2012-09-27 CA CA2850191A patent/CA2850191C/en not_active Expired - Fee Related
- 2012-09-27 US US14/345,998 patent/US9045618B2/en not_active Expired - Fee Related
- 2012-09-27 WO PCT/US2012/057501 patent/WO2013055524A1/en active Application Filing
- 2012-09-27 CN CN201280049692.8A patent/CN104114628B/zh not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1404498A (zh) * | 2000-02-21 | 2003-03-19 | 博里利斯技术公司 | 向聚合物颗粒中加入添加剂的方法 |
| CN101068868A (zh) * | 2003-12-04 | 2007-11-07 | 陶氏环球技术公司 | 稳定的聚乙烯材料 |
| CN101583639A (zh) * | 2006-10-11 | 2009-11-18 | 智利大学 | 用于制备纳米复合材料、微米复合材料和聚合物共混物的增容剂及其获得方法 |
| EP2163577A1 (en) * | 2008-09-15 | 2010-03-17 | Armacell Enterprise GmbH | Foamed thermoplastic cellular materials obtained by reactive extrusion process and with help of chain-extenders |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2850191C (en) | 2019-09-17 |
| SG11201401069TA (en) | 2014-04-28 |
| EP2766419A4 (en) | 2015-06-10 |
| US20140225038A1 (en) | 2014-08-14 |
| CA2850191A1 (en) | 2013-04-18 |
| RU2600321C2 (ru) | 2016-10-20 |
| CN104114628A (zh) | 2014-10-22 |
| WO2013055524A1 (en) | 2013-04-18 |
| BR112014008472A2 (pt) | 2017-05-16 |
| IN2014CN02605A (zh) | 2015-08-07 |
| JP6045001B2 (ja) | 2016-12-14 |
| RU2014118603A (ru) | 2015-11-20 |
| KR102013969B1 (ko) | 2019-10-21 |
| EP2766419A1 (en) | 2014-08-20 |
| KR20140077168A (ko) | 2014-06-23 |
| EP2766419B1 (en) | 2018-07-18 |
| US9045618B2 (en) | 2015-06-02 |
| JP2014530284A (ja) | 2014-11-17 |
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