CN106916432B - 用来稳定聚氧化烯烃聚醚多元醇，防止其氧化降解的方法 - Google Patents

用来稳定聚氧化烯烃聚醚多元醇，防止其氧化降解的方法 Download PDF

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CN106916432B
CN106916432B CN201611156675.0A CN201611156675A CN106916432B CN 106916432 B CN106916432 B CN 106916432B CN 201611156675 A CN201611156675 A CN 201611156675A CN 106916432 B CN106916432 B CN 106916432B
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陈华章
邓玫
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Abstract

本发明涉及一种用来稳定聚氧化烯烃聚醚多元醇，防止其氧化降解的方法。该法通过使用一种稳定剂组分，该组分包含对烷基苯酚和双环戊二烯的丁基化反应物，具有以下结构Formula I的多聚型受阻酚，

Description

用来稳定聚氧化烯烃聚醚多元醇，防止其氧化降解的方法
技术领域
本发明涉及一种用来稳定聚氧化烯烃聚醚多元醇，防止其氧化降解的方法；还涉及使用一种多聚型的受阻酚，用于稳定聚氧化烯烃聚醚多元醇，及使用此稳定剂获得的聚氨酯制品。该稳定剂是对烷基苯酚和双环戊二烯的丁基化反应物，具有以下结构FormulaI：
其中，n为0到10的整数，R为具有十二个或更少个碳的烷基。
背景技术
为抑制聚醚或聚氨酯制品的氧化降解，通常要添加抗氧化剂。目前常用的抗氧化剂包括单体型的叔丁酚类及其酯化产物，二烷基二苯胺，酚噻嗪类，亚磷酸酯，及以上物质的混合物。例如美国专利U.S.Pat.No.3,637,865，U.S.Pat.No.4,228,247和U.S.Pat.No.5,143,943。
2，6-二叔丁基-4-甲基苯酚(BHT)是其中常用的一种抗氧化剂，价廉而易得，可单独或与上述其他抗氧化剂共同用于稳定聚醚多元醇。但使用BHT有所缺陷，由于它易挥发，能逐渐迁移进入聚氨酯制品的覆盖物中(例如织物)，当环境中存在氮氧化物(″NOx″)，例如工业区或车流量较大的地区，会在覆盖物中反应形成显著的黄色色变。因此，有必要寻找不具有这种缺陷的氧化稳定剂。
本发明的目标在于提供一种替代BHT的合适，高效的稳定剂组分；具体来说，本发明发现一种多聚型的受阻酚，即对烷基苯酚和双环戊二烯的丁基化反应物，具有以下结构Formula I，高效、理想地适合于稳定具有分子量200到10000的聚氧化烯烃聚醚多元醇。
其中，n为0到10的整数，R为具有十二个或更少个碳的烷基。
发明内容
本发明的目的在于提供一种用来稳定具有分子量200到10000的聚氧化烯烃聚醚多元醇，防止其氧化降解的方法；该方法包含一种对烷基苯酚和双环戊二烯的丁基化反应物，即具有以下结构Formula I的多聚型受阻酚；其单独或联合其他抗氧化剂，加入到上述聚醚多元醇中；
其中，n为0到10的整数，R为具有十二个或更少个碳的烷基。
本发明还涉及提供包括以此方法稳定的多元醇，及以此多元醇或加入此稳定剂组分生产出的聚氨酯制品。
在聚氧化烯烃聚醚多元醇生产中，通常是单体型的叔丁酚类或其酯化产物作为主抗氧化剂，单独或复合其他抗氧化剂共同使用。常用的这类抗氧化剂如2，6-二叔丁基-4-甲基苯酚(″BHT″)，或者3，5-二叔丁基-4-羟基-苯基丙酸异辛酯(″1135″)，β-(3，5-二叔丁基-4-羟基苯基)丙酸正十八碳酯(″1076″)，四[β-(3，5-二叔丁基-4-羟基苯基)丙酸]季戊四醇酯(″1010″)，等等。然而，目前还无人研究过多聚型的叔丁酚类用于稳定聚氧化烯烃聚醚多元醇。
本发明发现一种多聚型受阻酚，即对烷基苯酚和双环戊二烯的丁基化反应物，具有以下结构Formula I，理想地适合于稳定具有分子量200到10000的聚氧化烯烃聚醚多元醇。
其中，n为0到10的整数，R为具有十二个或更少个碳的烷基。
该多聚物具有多个空间位阻羟基基团和高分子量，因而不挥发，不迁移且高效性。该多聚物可作为商品购得，或在酸性催化剂如三氟化硼存在下，利用对烷基苯酚和双环戊二烯反应，然后再与异丁烯烷基化反应制得，可参见专利US3305522。
基于聚氧化烯烃聚醚多元醇的分子结构，该多聚物与其他抗氧化剂复合使用也是适合的。一般情况下，相当于聚醚多元醇质量的0.01％到5％，较宜0.01％到1.0％的多聚型受阻酚，即对烷基苯酚和双环戊二烯的丁基化反应物，具有上述结构Formula I，可与相当于聚醚多元醇质量的0.01％到0.5％的其他结构的抗氧化剂联合使用，其他结构的抗氧化剂较宜为4，4′-二烷基二苯胺，包括二苯胺与二异丁烯的反应物。
使用本发明稳定剂组分稳定的聚氧化烯烃聚醚多元醇，包括含有2到10个羟基官能团，分子量从200至10000的聚氧化烯烃聚醚多元醇。该聚醚多元醇通过环氧衍生物与起始多官能度醇类反应制得。
在聚氨酯泡沫及聚氨酯制品的生产中，以本发明稳定剂组分稳定的聚氧化烯烃聚醚多元醇，在催化剂、表面活性剂、水及其他添加物存在的条件下，与含有两个以上N＝C＝O基团的多异氰酸酯进行反应。尽管该稳定剂组分通常预先加入到聚氧化烯烃聚醚多元醇中，但如果聚醚多元醇氧化降解方面没有问题，该稳定剂组分也可独立作为抗黄芯或稳定剂组分，与其他反应物一起加入到反应体系中，以制得聚氨酯泡沫及聚氨酯制品。当独立使用时，该稳定剂的组成和使用比例同前所述，基于反应体系中聚氧化烯烃聚醚多元醇的份量。
具体实施方式
以下例子基于本发明的原则，用来进一步阐述说明本发明，包括具有对比性的例子。但除了权利要求之外，这些举例不应视作对本发明的任何限制。
其中，聚氧化烯烃聚醚多元醇的氧化稳定性(衡量氧化降解)的测定，是通过把样品放置一梅特勒差示扫描量热仪中，记录其发生氧化时的温度。在此测定中，称重好的聚醚多元醇置于一坩埚中，然后与一参照物坩埚一起放入差示扫描量热仪的炉内。炉内的温度在氧气氛围下以每分钟10摄氏度的速率升温。温度记录在X轴上，吸收或释放的热量记录在Y轴上。截取热量曲线偏转的斜率与基线相交，以确定初始氧化时的温度。初始氧化温度越高，样品就越稳定。
下述配方用于测试聚氨酯泡沫的抗黄芯性能，其中抗氧稳定剂组分可预先添加于聚醚多元醇，或者单独与其他反应物一起加入到反应体系中：
前六个组分依次加入一纸碗中，然后以每分钟1000转速度混合搅拌45秒，加入辛酸亚锡继续以每分钟1000转速搅拌15秒。最后加入甲苯二异氰酸酯(TDI 80/20)，同时开始计时，以每分钟2500转速搅拌6秒，混合物迅速倒入箱体开始膨胀上升。当自倒入异氰酸酯计时达到300秒后，将所得泡沫移出箱体置于微波炉中，以50％功率烘烤6分钟。然后取出泡沫，在室温下继续熟化24小时，泡沫从中间切开，观察切面的色变情况。
实施例1
将几种不同用于替代BHT的抗氧化剂加入到一3000分子量，纯环氧丙烷(PO)聚合的聚氧化丙烃聚醚多元醇中，依上述方法测定其氧化稳定性，结果如下表1。其中多聚型受阻酚Formula I中R为甲基，平均分子量650。
本实施例通过比较在氧气氛围下的初始氧化温度，显示了与其他单体型叔丁酚类抗氧化剂相比，在同样添加量下，具有分子结构Formula I的多聚型的受阻酚，能显著提高聚醚多元醇的抗氧化降解稳定性。
表1
实施例2
本实施例中稳定剂组份包含不同主抗氧化剂(受阻酚)和另一抗氧化剂，分别加入到一3000分子量，与环氧丙烷(PO)和环氧乙烷(EO)聚合的聚氧化乙烯氧化丙烃聚醚多元醇中，依上述方法测定其氧化稳定性，结果如下表2：其中Formula I中R为甲基，平均分子量650。
本实施例通过比较在氧气氛围下的初始氧化温度，显示了当与其他抗氧化剂协同使用时，相比其他包含单体型叔丁酚类抗氧化剂组合，具有分子结构Formula I的多聚型受阻酚的组合使用量最小，而抗氧化降解稳定性最佳。因而更经济也更有效。
表2
实施例3
根据上述用于测试聚氨酯泡沫的抗黄芯性能的配方，使用不同的抗氧稳定剂组分分别进行实验制得聚氨酯泡沫并测试其抗黄芯效果。其中Formula I中R为甲基，平均分子量650。
如表3所示，本实施例显示当加入具有分子结构Formula I的多聚型受阻酚和另一抗氧化剂如4，4′-二异辛基二苯胺，即二苯胺与二异丁烯的反应物的组合，所制得的聚氨酯泡沫色变最小，抗黄芯效果更佳。
表3

Claims (4)

1.一种用于稳定具有分子量200到10000的聚氧化烯烃聚醚多元醇，防止其氧化降解的方法，其特征在于，所述方法通过加入稳定剂组分，所述稳定剂组分为复合成分，包含相当于所述聚醚多元醇质量的0.01％到1.0％的一种抗氧化剂，该抗氧化剂为对烷基苯酚和双环戊二烯的丁基化反应物，具有以下结构Formula I的多聚型受阻酚：
其中，n为0到10的整数，R为具有十二个或更少个碳的烷基；
还包含相当于所述聚醚多元醇质量的0.01％到0.5％的其他结构的抗氧化剂，所述其他结构的抗氧化剂为4,4'-二烷基二苯胺，包括二苯胺与二异丁烯的反应物。
2.一种根据权利要求1所述的方法进行稳定的分子量200到10000的聚氧化烯烃聚醚多元醇，其特征在于，在分子量200到10000的聚氧化烯烃聚醚多元醇中加入复合稳定剂组分；所述复合稳定剂组分包含相当于聚醚多元醇质量的0.01％到1.0％的一种抗氧化剂，该抗氧化剂为对烷基苯酚和双环戊二烯的丁基化反应物，具有上述结构Formula I的多聚型受阻酚，还包含相当于聚醚多元醇质量的0.01％到0.5％的其他结构的抗氧化剂，其他结构的抗氧化剂为4,4'-二烷基二苯胺，包括二苯胺与二异丁烯的反应物。
3.一种根据权利要求2所述的聚醚多元醇与多异氰酸酯反应制得的聚氨酯制品。
4.一种应用于权利要求1所述方法的稳定剂组分，其特征在于，所述稳定剂组分包含一种抗氧化剂，该抗氧化剂为对烷基苯酚和双环戊二烯的丁基化反应物，具有结构Formula I的多聚型受阻酚，添加量相当于聚醚多元醇质量的0.01％到1.0％；还包含其他结构的抗氧化剂，添加量相当于聚醚多元醇质量的0.01％到0.5％；所述稳定剂组分与其他反应物一起加入到反应体系中用于制备聚氨酯制品；所述其他结构的抗氧化剂为4,4'-二烷基二苯胺，包括二苯胺与二异丁烯的反应物。
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