CN115368632A - 一种亚磷酸酯抗氧剂组合物和使用其的合成树脂组合物 - Google Patents
一种亚磷酸酯抗氧剂组合物和使用其的合成树脂组合物 Download PDFInfo
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- CN115368632A CN115368632A CN202210810903.0A CN202210810903A CN115368632A CN 115368632 A CN115368632 A CN 115368632A CN 202210810903 A CN202210810903 A CN 202210810903A CN 115368632 A CN115368632 A CN 115368632A
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- antioxidant
- synthetic resin
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- phosphite
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Abstract
本发明公开了一种亚磷酸酯抗氧剂组合物和使用其的合成树脂组合物，亚磷酸酯抗氧剂组合物，其特征在于包含具有腰果酚结构的下述通式(1)所示的亚磷酸酯抗氧剂化合物，
所述通式(1)中R表示氢原子、羟基、碳原子数1～30的烷基或碳原子数1～30的烷氧基，烷基、烷氧基任选被单个或多个氧原子或羰基中断；所述通式(1)中n、m、k分别表示含单烯、双烯和三烯的腰果酚基团的个数，n、m、k均是大于等于0且小于等于3的整数，n、m与k三者之和为3。本发明提供了耐热性以及抗氧效果优于TNPP并且易于合成的常温液态亚磷酸酯的新型化合物，使用该化合物的合成树脂组合物，从用途上能够逐渐并全面的替代现有常规的TNPP，具有很好的应用前景。
Description
技术领域
本发明涉及耐热性和耐挥发性优良而且对树脂成分的相容性也优良的作为抗氧剂有用的新型化合物，具体涉及一种亚磷酸酯抗氧剂组合物和使用其的合成树脂组合物。
背景技术
诞生于20世纪的聚合物材料树脂，其在生产生活中的应用领域不断扩展，但作为有机类材料，容易发生氧化反应，从而呈现褪色、泛黄、硬化、龟裂、丧失光泽等表观现象，进而导致抗冲击强度、抗绕曲强度、抗张强度和伸长率等物理性能的大幅降低，影响材料的正常使用。
抗氧剂是抑制或延缓聚合物受氧化作用而降解的添加剂，是聚合物材料树脂(塑料、橡胶、纤维等)生产中应用最广泛的助剂，例如可以应用于聚丙烯、聚乙烯薄膜、高密度聚乙烯注塑产品、ABS、聚碳酸酯、聚酯模塑制品等各类聚合物材料制品中。聚合物抗氧剂从功能和作用机理上一般可分为主抗氧剂和辅助抗氧剂。主抗氧剂以捕捉聚合物氧化自由基或过氧自由基为主要功能，又称“自由基捕捉剂”，包括芳胺类和受阻酚类等化合物；辅助抗氧剂具有分解聚合物过氧化合物，防止其裂解诱发聚合物热氧降解，又称“过氧化物分解剂”，目前市场上主流品种包括硫醚类和亚磷酸酯类抗氧剂，通常和主抗氧剂配合使用，具有很好的协同作用。
亚磷酸酯类抗氧剂能够显著提高聚合物的高温加工稳定性，能最大限度地抑制聚合物加工时的色泽和熔融指数变化，改善塑料制品的色泽以及熔融指数稳定性。目前应用较多的亚磷酸酯类抗氧剂品种有抗氧剂168和抗氧剂TNPP都属于通用型辅助抗氧剂。其中抗氧剂TNPP常温下为液体，耐热性和耐挥发性优良，与多种类聚合物或基质的相容性好，应用领域广，特别是可以应用在液态产品中，不会引起固化。可以应用在弹性体、胶粘剂、通用塑料以及加工温度较低的工程塑料(SBS、TPR、IPS、PS、SBR、BR、PVC、PE、PP、ABS等)、增塑剂、工业脂肪、矿物油等其它有机基质。从而保护那些暴露于氧化环境中的聚合体，避免其在加工过程中(混合、造粒、成型、回收应用)的分子量的改变(比如：链的断裂和交联)及基质的色变。
尽管抗氧剂TNPP性能优异但由于它的原料为壬基酚，使得它遇水会逐渐水解生成壬基酚，而壬基酚是环境激素中毒性最大、最难被生物降解的污染物，通过对生物内分泌***造成严重影响，从而对水生生物、哺乳动物等均显现了不同程度的毒性，恶化了生物的存活、发育及生长。
腰果酚由腰果油(也称腰果壳液)中提取而来纯天然产物，腰果油经真空蒸馅可得较为纯净的腰果酚。天然腰果油是从热带漆科植物腰果树的果实的壳中榨取而得的棕色粘稠性液体。腰果树果实长2-4cm,外壳呈蜂窝状结构，内含油状液体，称之为腰果油。随着业界对腰果油组成研究的深入，确定了腰果油中约含90％的腰果酚和10％的强心酚，并进一步对腰果酚的组成和结构有了一个清楚的认识。腰果酚的结构如下所示：
腰果酚是具有饱和或不饱和长链烃基C15H25-31的天然酚类化合物，类似于漆酚。腰果酚既有芳香族化合物的特征，又类似于脂肪族化合物的特征，同时，苯环上的酚羟基又使其具有酚类的性质。腰果酚的饱和、单烯、双烯和三烯等组分均为淡黄色油状液体，含量依次为，腰果酚不溶于水，可溶于乙醇、乙髄、醋酸丁酯、二甲苯、丙酮、环已烷、氯仿等有机溶剂。
发明内容
针对现有技术存在的上述技术问题，本发明的目的在于提供耐热性以及抗氧效果优于TNPP并且易于合成的常温液态亚磷酸酯的新型化合物以及使用了该化合物的合成树脂组合物，从而在各种用途上能够逐渐并全面的替代TNPP。
对于常温液态亚磷酸酯的新型化合物，易于合成指的是使用无毒无害的酚类化合物作为原料，用一步反应法合成常温液态亚磷酸酯的新型化合物。
本发明者为了解决上述课题而进行了深入研究，结果发现了作为合成树脂用的辅助抗氧剂的有用的具有腰果酚结构的特定的新型亚磷酸酯化合物的混合物，并且因为该类亚磷酸酯化合物结构的特点是含有烯烃基酚，烯烃也具有还原活性，即该类结构具有比含有烷基酚结构的TNPP更高的抗氧活性，而且该类新型亚磷酸酯化合物的混合物中的各成分结构相近，都具有高抗氧活性和高耐热性，无需分离而能够以混合物的形式直接作为抗氧剂发挥效果，从而完成了本发明。
即，本发明提供一种简便的合成方法，使用腰果酚作为原料，一步法合成具有高抗氧活性新型亚磷酸酯化合物的混合物。由于腰果酚本身成分的特点，以上合成的是新型亚磷酸酯化合物的混合物，其主要成分由下述通式(1)表示：
所述通式(1)中R表示氢原子、羟基、碳原子数1～30的烷基或碳原子数1～30的烷氧基，烷基、烷氧基任选被单个或多个氧原子或羰基中断。所述通式(1)中R优选为氢原子、羟基、碳原子数1～20的烷基或碳原子数1～20的烷氧基。
作为碳原子数为1～20的烷基，可以列举出甲基、乙基、丙基、2-丙炔基、丁基、异丁基、仲丁基、叔丁基、戊基、异戊基、己基、癸基、十二烷基、十八烷基等。作为碳原子数为1～20的烷氧基，可以列举出例如甲氧基、乙氧基、异丙氧基、丁氧基、仲丁氧基、叔丁氧基、异丁氧基、戊氧基、异戊氧基、叔戊氧基、己氧基、2-己氧基、3-己氧基、环己氧基、4-甲基环己氧基、庚氧基、2-庚氧基、3-庚氧基、异庚氧基、叔庚氧基、1-辛氧基、异辛氧基、叔辛氧基等。
所述通式(1)中n、m、k分别表示含单烯、双烯和三烯的腰果酚基团的个数，n、m、k均是大于等于0且小于等于3的整数，n、m与k三者之和为3。而通式(1)的结构可以列举为下式(2)中典型的2-1，2-2，2-3化合物，以及下式(3)中典型的3-1，3-2化合物，以及下式(4)中典型的4-1，4-2化合物，以及下式(5)中典型的5-1，5-2化合物，以及下式(6)中典型的6-1化合物：
此外，本发明提供一种液态或固态抗氧剂组成物(也称稳定剂组成物)，其是相对于抗氧剂组成物100质量份含有上述通式(1)表示的新型亚磷酸酯化合物10～100质量份。即是抗氧剂组成物中可以是含有质量分数10～100％的通式(1)所示的亚磷酸酯抗氧剂化合物。
另外，本发明提供一种合成树脂组合物，其是相对于合成树脂100质量份配合上述通式(1)表示的新型亚磷酸酯化合物0.001～20质量份而成的。
另外，本发明提供一种合成树脂组合物，其是相对于合成树脂100质量份配合上述通式(1)表示的新型亚磷酸酯化合物0.001～10质量份而成的。
本发明提供上述合成树脂组合物，其中，上述合成树脂是聚氨酯树脂、聚酯树脂、聚烯烃树脂、含聚丁二烯段或聚戊二烯段的嵌段聚合物(比如，SBS、TPR、IPS、SBR、BR、ABS等)。
本发明的含有质量分数10％-100％上述通式(1)表示的新型亚磷酸酯化合物的抗氧剂组合物配合于合成树脂中，制成以下说明的合成树脂组合物来用于各种用途中。
下面，对本发明的合成树脂组合物进行说明。
本发明的合成树脂组合物是通过在合成树脂中，混配有含有质量分数10％-100％上述通式(1)表示的新型亚磷酸酯化合物的混合物作为抗氧剂而成的，即是合成树脂的抗氧剂100质量份中含有上述通式(1)表示的新型亚磷酸酯化合物10～100质量份。
在本发明的合成树脂组合物中，针对100质量份的树脂，含有质量分数10％-100％上述通式(1)表示的新型亚磷酸酯化合物的抗氧剂混合物配合量为0.01～20质量份，从对树脂的相容性、耐热性、耐候性、耐挥发性的观点出发，优选为0.01～10质量份、更优选为0.03～5质量份、进一步优选为0.004～3质量份。抗氧剂混合物的配合量如果低于0.01质量份，则耐热性、耐候性差，如果超过20质量份，则对树脂的相容性差。
作为本发明中使用的合成树脂，可以列举出：聚丙烯、高密度聚乙烯、低密度聚乙烯、直链低密度聚乙烯、聚丁烯-1、聚-4-甲基戊烯等α-烯烃聚合物或乙烯-醋酸乙烯酯共聚物、乙烯-丙烯共聚物等聚烯烃以及它们的共聚物；聚氯乙烯、聚偏氯乙烯、氯化橡胶、氯乙烯-醋酸乙烯酯共聚物、氯乙烯-乙烯共聚物、氯乙烯-偏氯乙烯共聚物、氯乙烯-偏氯乙烯-醋酸乙烯酯三元共聚物、氯乙烯-丙烯酸酯共聚物、氯乙烯-马来酸酯共聚物、氯乙烯-环己基马来酰亚胺共聚物等含卤树脂；石油树脂；香豆酮树脂；聚苯乙烯；聚醋酸乙烯酯；丙烯酸树脂；苯乙烯和/或α-甲基苯乙烯与其它的单体(例如马来酸酐、苯基马来酰亚胺、甲基丙烯酸甲酯、丁二烯、丙烯腈等)的共聚物(例如AS树脂、ABS树脂、MBS树脂、耐热ABS树脂等)；聚甲基丙烯酸甲酯、聚乙烯醇、聚乙烯醇缩甲醛、聚乙烯丁缩醛、聚对苯二甲酸乙二醇酯、聚对苯二甲酸丁二醇酯、聚对苯二甲酸丁二醇酯等直链聚酯；聚苯醚、聚己内酰胺和聚己二酰己二胺等聚酰胺、聚碳酸酯、支链聚碳酸酯、聚缩醛、聚苯硫醚、聚氨酯、纤维素系树脂等热塑性树脂以及它们的混合物；或者酚醛树脂、尿素树脂、蜜胺树脂、环氧树脂、不饱和聚酯树脂等热固性树脂。进而，也可以是异戊二烯橡胶、丁二烯橡胶、丙烯腈-丁二烯共聚橡胶、苯乙烯-丁二烯共聚橡胶等弹性体，也可以被包含在上述树脂中。
上述这些合成树脂不论分子量、聚合度、密度、软化点、在溶剂中的不溶成分的比例、立构规整性的程度、催化剂残渣的有无、作为原料的单体的种类和配合比率、聚合催化剂的种类(例如齐格纳催化剂、茂金属催化剂等)等怎样，都可以使用。
本发明的合成树脂组合物中，作为合成树脂，从对树脂的相容性、耐黄变的迫切性的观点出发，优选聚碳酸酯树脂、聚酯树脂、丙烯酸树脂、ABS树脂，更优选聚碳酸酯树脂和ABS树脂的合金树脂。
聚碳酸酯树脂可以是通常市售的那些，例如，使1种以上的双酚类与光气或碳酸二酯反应而得到的聚碳酸酯树脂；或者使1种以上的双酚类与碳酸二苯酯类通过酯交换法反应而得到的聚碳酸酯树脂等。作为双酚类，可以列举出例如氢醌、4，4-二羟基苯基、双(4-羟基苯基)-烷烃、双(4-羟基苯基)-环烷烃、双(4-羟基苯基)硫化物、双(4-羟基苯基)醚、双(4-羟基苯基)酮、双(4-羟基苯基)砜、双酚芴或它们的烷基取代物、芳基取代物、卤素取代物等，它们可以使用1种2种以上组合使用。上述这样的聚碳酸酯中，以2，2-双(4-羟基苯基)丙烷即所谓的双酚A为原料的双酚A系聚碳酸酯从能够容易在市场上获得的观点出发是优选的。另外，聚碳酸酯树脂不仅可以是聚碳酸酯为100％的树脂，还可以是聚碳酸酯与其它的树脂混合而成的所谓聚合物合金。作为这样的聚合物合金，可以列举出例如聚碳酸酯/ABS树脂、聚碳酸酯/AS树脂、聚碳酸酯/橡胶系高分子化合物、聚碳酸酯/ABS树脂/橡胶系高分子化合物、聚碳酸酯/聚对苯二甲酸乙二醇酯、聚碳酸酯/聚对苯二甲酸丁二醇酯、聚碳酸酯/ASA树脂、聚碳酸酯/AES树脂等。
在使用聚碳酸酯树脂和ABS树脂的合金树脂作为合成树脂的情况下，由上述通式(1)表示的亚磷酸酯化合物的含量是相对于聚氨酯树脂100质量份为0.01～10质量份，从耐热性、耐候性和相容性的观点出发，优选为0.05～3质量份，更优选为0.1～2质量份。
本发明的合成性树脂组合物中，在不损害本发明的效果的范围内，根据需要还可以使用酚系抗氧化剂、硫醚系抗氧化剂、受阻胺系光稳定剂、含三嗪环的化合物、金属氢氧化物、磷酸酯系阻燃剂、缩合磷酸酯系阻燃剂、磷酸酯系阻燃剂、无机磷系阻燃剂、(聚)磷酸盐系阻燃剂、卤素系阻燃剂、硅系阻燃剂、氧化锑、无机系阻燃助剂、有机系阻燃助剂、抗静电剂、润滑剂、成核剂、增塑剂、脱模剂、相容化剂、发泡剂、光吸収性色素、颜料、染料、加工助剂、金属惰性化剂、无机微粒、抗菌剂、防霉剂、填充剂、填料等。另外，在不损害本发明的效果的范围内还可以使用由上述通式(1)表示的亚磷酸酯化合物以外的亚磷酸酯抗氧剂。上述添加剂的配合量是，相对于合成树脂100质量份优选合计为10质量份以下。
作为上述酚系抗氧化剂，可以列举出例如2，6-二叔丁基-对甲酚、2，6-二苯基-4-十八烷氧基苯酚、二硬脂酰基(3，5-二叔丁基-4-羟基苄基)膦酸酯、1，6-六亚甲基双[(3，5-二叔丁基-4-羟基苯基)丙酸酰胺]、4，4’-硫代双(6-叔丁基-间甲酚)、2，2’-亚甲基双(4-甲基-6-叔丁基苯酚)、2，2’-亚甲基双(4-乙基-6-叔丁基苯酚)、4，4’-丁叉双(6-叔丁基-间甲酚)、2，2’-乙叉双(4，6-二叔丁基苯酚)、2，2’-乙叉双(4-叔丁基-6-叔丁基苯酚)、1，1，3-三(2-甲基-4-羟基-5-叔丁基苯基]丁烷、1，3，5-三(2，6-二甲基-3-羟基-4-叔丁基苄基)异氰脲酸酯、1，3，5-三(3，5-二叔丁基-4-羟基苄基)异氰脲酸酯、1，3，5-三(3，5-二叔丁基-4-羟基苄基)-2，4，6-三甲基苯、2-叔丁基-4-甲基-6-(2-丙烯酰氧基-3-叔丁基-5-甲基苄基)苯酚、硬脂酰基(3，5-二叔丁基-4-羟基苯基)丙酸酯、四[3-(3，5-二叔丁基-4-羟基苯基)丙酸甲酯]甲烷、硫代二乙二醇双[(3，5-二叔丁基-4-羟基苯基)丙酸酯]、1，6-六亚甲基双[(3，5-二叔丁基-4-羟基苯基)丙酸酯]、双[3，3-双(4-羟基-3-叔丁基苯基)丁酸]二醇酯、双[2-叔丁基-4-甲基-6-(2-羟基-3-叔丁基-5-甲基苄基)苯基]对苯二甲酸酯、1，3，5-三[(3，5-二叔丁基-4-羟基苯基)丙酰氧基乙基]异氰脲酸酯、3，9-双[1，1-二甲基-2-{(3-叔丁基-4-羟基-5-甲基苯基)丙酰氧基}乙基]-2，4，8，10-四氧杂螺[5，5]十一烷、三乙二醇双[(3-叔丁基-4-羟基-5-甲基苯基)丙酸酯]等。上述这些酚系抗氧化剂的添加量是，相对于合成树脂100质量份优选为0.01～10质量份、更优选为0.05～3质量份。
作为上述硫醚系抗氧化剂，可以列举出例如硫代二丙酸二月桂酯、硫代二丙酸二肉豆蔻酯、硫代二丙酸二硬脂酯等硫代二丙酸二烷基酯类、以及季戊四醇四(β-烷基硫代丙酸)酯类。上述这些硫醚系抗氧化剂的添加量是，相对于合成树脂100质量份优选为0.001～10质量份、更优选为0.05～5质量份。
作为上述受阻胺系光稳定剂，可以列举出例如2，2，6，6-四甲基-4-哌啶基硬脂酸酯、1，2，2，6，6-五甲基-4-哌啶基硬脂酸酯、2，2，6，6-四甲基-4-哌啶基苯甲酸酯、双(2，2，6，6-四甲基-4-哌啶基)癸二酸酯、双(1，2，2，6，6-五甲基-4-哌啶基)癸二酸酯、双(1-辛氧基-2，2，6，6-四甲基-4-哌啶基)癸二酸酯、四(2，2，6，6-四甲基-4-哌啶基)-1，2，3，4-丁烷四羧酸酯、四(1，2，2，6，6-五甲基-4-哌啶基)-1，2，3，4-丁烷四羧酸酯、双(2，2，6，6-四甲基-4-哌啶基)·二(十三烷基)-1，2，3，4-丁烷四羧酸酯、双(1，2，2，6，6-五甲基-4-哌啶基)·二(十三烷基)-1，2，3，4-丁烷四羧酸酯、双(1，2，2，4，4-五甲基-4-哌啶基)-2-丁基-2-(3，5-二叔丁基-4-羟基苄基)丙二酸酯、1-(2-羟基乙基)-2，2，6，6-四甲基-4-哌啶醇/琥珀酸二乙酯缩聚物、1，6-双(2，2，6，6-四甲基-4-哌啶基氨基)己烷/2，4-二氯-6-吗啉代-均三嗪缩聚物、1，6-双(2，2，6，6-四甲基-4-哌啶基氨基)己烷/2，4-二氯-6-叔辛基氨基-均三嗪缩聚物、1，5，8，12-四[2，4-双(N-丁基-N-(2，2，6，6-四甲基-4-哌啶基)氨基)-均三嗪-6-基]-1，5，8，12-四氮杂十二烷、1，5，8，12-四[2，4-双(N-丁基-N-(1，2，2，6，6-五甲基-4-哌啶基)氨基)-均三嗪-6-基]-1，5，8，12-四氮杂十二烷、1，6，11-三[2，4-双(N-丁基-N-(2，2，6，6-四甲基-4-哌啶基)氨基)-均三嗪-6-基氨基]十一烷、1，6，11-三[2，4-双(N-丁基-N-(1，2，2，6，6-五甲基-4-哌啶基)氨基)-均三嗪-6-基]氨基十一烷等受阻胺化合物。上述这些受阻胺系光稳定剂的添加量是，相对于合成树脂100质量份优选为0.01～35质量份、更优选为0.1～8质量份。
作为上述含三嗪环的化合物，可以列举出例如三聚氰胺、三聚氰酸二酰胺、苯并胍胺、乙酰胍胺、邻苯二胍胺(phthalodiguanamine)、三聚氰胺异氰脲酸酯、焦磷酸三聚氰胺、亚丁基二胍胺、降冰片烯二胍胺、亚甲基二胍胺、亚乙基双三聚氰胺、三亚甲基双三聚氰胺、四亚甲基双三聚氰胺、六亚甲基双三聚氰胺、1，3-亚己基双三聚氰胺等。
作为上述金属氢氧化物，可以列举出例如氢氧化镁、氢氧化铝、氢氧化钙、氢氧化钡、氢氧化锌、KISUMA 5A(氢氧化镁：协和化学工业株式会社制)等。
作为上述磷酸酯系阻燃剂，可以列举出例如磷酸三甲酯、磷酸三乙酯、磷酸三丁酯、三丁氧基乙基磷酸酯、三氯代乙基磷酸酯、三(二氯丙基)磷酸酯、磷酸三苯酯、磷酸三甲苯酯、甲苯基二苯基磷酸酯、三(二甲苯基)磷酸酯、辛基二苯基磷酸酯、二甲苯基二苯基磷酸酯、三异丙基苯基磷酸酯、2-乙基己基二苯基磷酸酯、叔丁基苯基二苯基磷酸酯、双(叔丁基苯基)苯基磷酸酯、三(叔丁基苯基)磷酸酯、异丙基苯基二苯基磷酸酯、双(异丙基苯基)二苯基磷酸酯、三(异丙基苯基)磷酸酯等。
作为上述缩合磷酸酯系阻燃剂的例子，可以列举出1，3-亚苯基双(二苯基磷酸酯)、1，3-亚苯基双(二(二甲苯基)磷酸酯)、双酚A双(二苯基磷酸酯)等。
作为上述(聚)磷酸盐系阻燃剂的例子，可以列举出聚磷酸铵、聚磷酸三聚氰胺、聚磷酸哌嗪、焦磷酸三聚氰胺、焦磷酸哌嗪等(聚)磷酸的铵盐和胺盐。
作为上述无机系阻燃助剂，可以列举出例如氧化钛、氧化铝、氧化镁、水滑石、滑石、蒙脱石等无机化合物。
作为上述有机系阻燃助剂，可以列举出例如季戊四醇。
作为上述抗静电剂，可以列举出例如脂肪酸季铵离子盐、聚胺四级盐等阳离子系抗静电剂；高级醇磷酸酯盐、高级醇环氧乙烷加成物、聚乙二醇脂肪酸酯、阴离子型的烷基磺酸盐、高级醇硫酸酯盐、高级醇环氧乙烷加成物硫酸酯盐、高级醇环氧乙烷加成物磷酸酯盐等阴离子系抗静电剂；多元醇脂肪酸酯、聚二醇磷酸酯、聚氧乙烯烷基烯丙基醚等非离子系抗静电剂；烷基二甲基氨基醋酸甜菜碱等两性型烷基甜菜碱、咪唑啉型两性活性剂等两性抗静电剂。
作为上述润滑剂，可以列举出例如流动石蜡、固体蜡、聚乙烯蜡等烃系润滑剂；硬脂醇、硬脂酸、12-羟基硬脂酸等脂肪族系润滑剂；硬脂酸酰胺、油酸酰胺、芥子酸酰胺、亚甲基双硬脂酸酰胺、亚乙基硬脂酸酰胺等酰胺系润滑剂；硬脂酸钙、硬脂酸锌、硬脂酸镁、硬脂酸铅、硬脂酸铝、硬脂酸钡、硬脂酸钡/硬脂酸锌复合物、硬脂酸锌/硬脂酸钙复合物等金属皂系润滑剂；硬化油脂、丙三醇单硬脂酸酯、硬脂酸丁酯、季戊四醇硬脂酸酯、硬脂酸硬脂酯等酯系润滑剂。
作为上述成核剂，可以列举出例如二苄叉山梨糖醇、双(对甲基亚苄基)山梨糖醇、双(对乙基亚苄基)山梨糖醇、羟基-二(叔丁基安息香酸)铝、磷酸双(4-叔丁基苯基)钠、磷酸2，2-亚甲基双(4，6-二叔丁基苯基)钠盐等成核剂。
作为上述增塑剂，可以列举出例如邻苯二甲酸酯、二元酸酯、氯化石蜡、聚酯、环氧化酯、磷酸酯、偏苯三酸酯等增塑剂。
作为上述填充剂，可以列举出例如硅酸钙粉、二氧化硅粉、滑石粉、云母粉、氧化铝粉、氧化钛粉、玻璃片等。
作为上述填料，可以列举出玻璃纤维、碳纤维等。
作为上述紫外线吸收剂(也称作其它的紫外线吸收剂)，可以列举出例如2，4-二羟基二苯甲酮、2-羟基-4-甲氧基二苯甲酮、2-羟基-4-辛氧基二苯甲酮、5，5’-甲叉双(2-羟基-4-甲氧基二苯甲酮)等2-羟基二苯甲酮类；2-(2’-羟基-5’-甲基苯基)苯并***、2-(2’-羟基-3’，5’-二叔丁基苯基)-5-氯苯并***、2-(2’-羟基-3’-叔丁基-5’-甲基苯基)-5-氯苯并***、2-(2’-羟基-5’-叔辛基苯基)苯并***、2-(2’-羟基-3’，5’-二枯基苯基)苯并***、2，2’-甲叉双(4-叔辛基-6-(苯并***基)苯酚)、2-(2’-羟基-3’-叔丁基-5’-羧基苯基)苯并***等2-(2’-羟基苯基)苯并***类；水杨酸苯酯、间苯二酚单苯甲酸酯、2，4-二叔丁基苯基-3，5-二叔丁基-4-羟基苯甲酸酯、2，4-二叔戊基苯基-3，5-二叔丁基-4-羟基苯甲酸酯、十六烷基-3，5-二叔丁基-4-羟基苯甲酸酯等苯甲酸酯类；2-乙基-2’-乙氧基草酰替苯胺、2-乙氧基-4’-十二烷基草酰替苯胺等取代草酰替苯胺类；乙基-α-氰基-β，β-二苯基丙烯酸酯、甲基-2-氰基-3-甲基-3-(对甲氧基苯基)丙烯酸酯、季戊四醇四(2-氰基-3，3-二苯基丙烯酸酯)等氰基丙烯酸酯类；2-(2-羟基-4-辛氧基苯基)-4，6-双(2，4-二叔丁基苯基)-均三嗪、2-(2-羟基-4-甲氧基苯基)-4，6-二苯基-均三嗪、2-(2-羟基-4-丙氧基-5-甲基苯基)-4，6-双(2，4-二叔丁基苯基)-均三嗪等三芳基三嗪类。
紫外线吸收剂的配合量是相对于合成树脂100质量份优选为3质量份以下。
作为由上述通式(1)表示的亚磷酸酯以外的亚磷酸酯抗氧剂，可以列举出例如亚磷酸三(壬基苯基)酯、三[2-叔丁基-4-(3-叔丁基-4-羟基-5-甲基苯硫基)-5-甲基苯基]亚磷酸酯、亚磷酸三癸酯、辛基二苯基亚磷酸酯、二(癸基)单苯基亚磷酸酯、二(十三烷基)季戊四醇二亚磷酸酯、二(壬基苯基)季戊四醇二亚磷酸酯、双(2，4-二叔丁基苯基)季戊四醇二亚磷酸酯、双(2，6-二叔丁基-4-甲基苯基)季戊四醇二亚磷酸酯、双(2，4，6-三叔丁基苯基)季戊四醇二亚磷酸酯、双(2，4-二枯基苯基)季戊四醇二亚磷酸酯、四(十三烷基)异丙叉二苯酚二亚磷酸酯、四(十三烷基)-4，4’-正丁叉双(2-叔丁基-5-甲基苯酚)二亚磷酸酯、六(十三烷基)-1，1，3-三(2-甲基-4-羟基-5-叔丁基苯基)丁烷三亚磷酸酯、四(2，4-二叔丁基苯基)亚联苯基二亚膦酸酯、9，10-二氢-9-氧代-10-磷杂菲-10-氧化物、2，2’-亚甲基双(4，6-叔丁基苯基)-2-乙基己基亚磷酸酯、2，2’-亚甲基双(4，6-叔丁基苯基)-十八烷基亚磷酸酯、2，2’-乙叉双(4，6-二叔丁基苯基)氟代亚磷酸酯、三(2-[(2，4，8，10-四叔丁基二苯并[d，f][1，3，2]二氧杂磷庚烯-6-基)氧]乙基)胺、2-乙基-2-丁基丙二醇与2，4，6-三叔丁基苯酚的亚磷酸酯等。
在使用其它的亚磷酸酯抗氧剂的情况下，其配合量是相对于合成树脂100质量份优选为3质量份以下。
本发明的合成树脂组合物的制造方法没有特别限制，可以采用以往公知的任意的树脂组合物的制造方法。
具体地说，可以列举出例如下述方法：将合成树脂和上述通式(1)的抗氧剂剂、根据需要添加的其它合成树脂添加剂成分使用滚混机或亨歇尔混合机等各种混合机预先混合后，用密炼机、辊炼机、单螺杆混炼挤出机、双螺杆混炼挤出机、捏合机等进行熔融混炼。
另外，也可以不将各成分预先混合，而仅将一部分出发预先混合，并使用进料器供给至挤出机，进行熔融混炼，从而制造树脂组合物。另外，也可以将通过预先混合一部分成分并供给至挤出机进行熔融混炼而得到的树脂组合物制成母料，再次与其它成分混合并进行熔融混炼，从而制作树脂组合物。
即，本发明的合成树脂组合物及其成型体可以用于电气/电子/通信、农林水产、矿业、建设、食品、纤维、衣类、医疗、煤炭、石油、橡胶、皮革、汽车、精密仪器、木材、建材、土木、家具、印刷、乐器等广泛的产业领域。更具体地说，可以用于：打印机、电脑、文字处理机、键盘、PDA(小型信息末端机)、电话机、复印机、传真、ECR(电子式现金收入记录机)、计算器、电子笔记本、卡、架子、文具等办公用品、OA设备；洗衣机、冰箱、吸尘器、微波炉、照明器具、游戏机、熨斗、被炉等家电设备；TV、VTR、摄像机、收录机、录音机、小型唱片、CD播放器、扩音器、液晶显示器等AV设备、连接器、继电器、电容器、开关、印刷基板、绕线管、半导体密封材料；LED密封材料、电线、电缆、变压器、偏转轭、分电盘、钟表等电气/电子部件和通信设备、OA设备等的箱体(框架、框体、外壳、外装)和部件；汽车内外装材的用途；以及座位(填充物、面料等)、传动带、吊顶、汽车顶篷、扶手、门装饰条、后窗台盘、地毯、垫子、遮阳罩、箔罩、垫罩、气囊、绝缘材、吊绳、吊带、电线覆盖材、电绝缘材、涂料、涂布材、表面覆盖材、地板材、角壁、地毯、壁纸、壁装材、外装材、内装材、屋顶材、甲板材、壁材、柱材、地板、墙的材料、骨架和装饰条、窗户和门的型材形材、薄木板、板壁、阳台、露台、防音板、绝热板、窗户材等汽车、混合动力型车、电动车、车辆、船舶、飞机、建筑物、住宅和建筑用材料；土木材料；衣料、窗帘、床单、胶合板、复合纤维板、绒毯、玄关垫、片材、桶、软管、容器、眼镜、包、盒子、护目镜、滑雪板、球拍、帐篷、乐器等生活用品、体育用品等各种用途。
附图说明
图1为合成例1的新型亚磷酸酯化合物的混合物NO.1的P31(CDCl3)谱图；
图2为合成例1的新型亚磷酸酯化合物的混合物NO.1的C13(CDCl3)谱图；
图3为合成例1的新型亚磷酸酯化合物的混合物NO.1的FT-IR谱图。
具体实施方式
下面结合具体实施例对本发明作进一步说明，但本发明的保护范围并不限于此。
合成例1
在五口的1000ml烧瓶上安装搅拌机、氮气导入管、温度计、精馏管和旋塞(取样用)，再在精馏管的前端安装水分定量接收器、冷却管，使用上述装置作为反应装置。在上述烧瓶中加入作为原料的酚成分的腰果酚(86.0g，约0.3摩尔，浙江万盛股份有限公司精制)，作为溶剂的二甲苯(300.0g)、作为催化剂的三乙胺(0.2g、2毫摩尔)，在常压以及70℃下，滴加作为原料的三氯化磷(13.7g，0.1摩尔，浙江万盛股份有限公司精制)。滴加完毕后，体系升温至回流(>135℃)，一边将生成氯化氢除去到体系外，一边进行酯化反应。用HPLC分析出原料低于1％的时候结束酯化反应。之后，降温进行减压蒸馏以便于脱除溶剂，接着进行过滤，从而制造作为目标物的上述通式(1)表示的新型亚磷酸酯化合物的混合物NO.1，收率为95％。
上述通式(1)表示的新型亚磷酸酯化合物的混合物NO.1的鉴定是使用核磁和红外进行，鉴定结果如下所示。
上述通式(1)表示的新型亚磷酸酯化合物的混合物NO.1的P31(CDCl3)谱图为图1，作为主要成分通式(1)表示的新型亚磷酸酯化合物的混合物的化学位移为128ppm，呈现单峰。C13(CDCl3)谱图为图2，作为主要成分通式(1)表示的新型亚磷酸酯化合物的混合物的化学位移为13.91ppm、14.23ppm、22.78ppm、22.90ppm、25.68ppm、25.76ppm、27.30ppm、27.32ppm、27.33ppm、29.10ppm、29.33ppm、29.39ppm、29.51ppm、29.74ppm、29.77ppm、29.85ppm、29.87ppm、31.35ppm、31.62ppm、31.90ppm、35.88ppm、76.85ppm、77.16ppm、77.48ppm、114.80ppm、117.95ppm、118.02ppm、120.77ppm、120.84ppm、124.34ppm、126.88ppm、127.69ppm、128.11ppm、128.25ppm、128.29ppm、129.10ppm、129.38ppm、129.88ppm、129.96ppm、130.02ppm、130.14ppm、130.41ppm、136.84ppm、144.91ppm、144.93ppm、151.70ppm、151.74ppm。
上述通式(1)表示的新型亚磷酸酯化合物的混合物NO.1的红外谱图为图3所示，其中691cm-1、806cm-1、945cm-1为苯环的弯曲振动峰，2853cm-1、2924cm-1、3009cm-1为C-H伸缩振动峰。
合成例2
在五口的1000ml烧瓶上安装搅拌机、氮气导入管、温度计、精馏管和旋塞(取样用)，再在精馏管的前端安装水分定量接收器、冷却管，使用上述装置作为反应装置。在上述烧瓶中加入作为原料的酚成分的腰果酚(86.0g，约0.3摩尔，浙江万盛股份精制)，作为溶剂的二甲苯(300.0g)、作为催化剂的三乙胺(30g、0.3摩尔)，在常压以及室温下，滴加作为原料的三氯化磷(13.7g，0.1摩尔，浙江万盛股份精制)。滴加完毕后，体系升温至40℃，保持2小时以上。用HPLC分析出原料低于1％的时候结束酯化反应。之后，降温进行过滤，然后进行减压蒸馏除去溶剂，从而制造作为目标产物NO.2，收率为97％。
通过核磁和红外进行比对，确认了目标产物NO.2与化合物NO.1相同，为上述通式(1)表示的新型亚磷酸酯化合物的混合物。
[实施例1-1和比较例1-1]
<耐热加工性能评价>
对合成例1中得到的上述通式(1)表示的新型亚磷酸酯化合物的混合物或作为比较化合物的TNPP，通过示差热分析进行耐热加工性能的评价。评价是用1％和3％热重损失温度来检验，进行TGA测试时是以室温为起始温度，以5℃/min的速率升温，记录1％和3％重量损失时的温度，结果示于表1中，而热重损失温度越高表明亚磷酸酯的耐热加工性能越好。结果表明上述通式(1)表示的新型亚磷酸酯化合物的混合物的耐热加工性能明显优于TNPP。
表1.亚磷酸酯化合物耐热性的比较(TGA)
[实施例2-1和比较例2-1]
<TVOC评价>
对合成例1中得到的上述通式(1)表示的新型亚磷酸酯化合物的混合物或作为比较化合物的TNPP，通过示差热分析进行TVOC的评价。评价是用TVOC测试值来检验。结果示于表2中，而TVOC越低表明亚磷酸酯的耐挥发性能越好，越有利于作为抗氧剂来使用。结果表明上述通式(1)表示的新型亚磷酸酯化合物的混合物的TVOC明显优于TNPP。
表2.亚磷酸酯化合物挥发性的比较(TVOC)
[实施例3-1和比较例3-1]
[试验片的制作]
相对于下述表3中记载的PC/ABS合金树脂100质量份，按照表3中记载的配合量配合合成例1中得到的上述通式(1)表示的新型亚磷酸酯化合物的混合物或作为比较化合物的TNPP，在230℃下使用挤出机(南京盛驰橡塑机械制造有限公司所制、35机)制作粒料，配方1#所得粒料为粒料A，配方2#所得粒料为粒料B。用上述粒料A或B再次在230℃下使用挤出机制作粒料，分别得到粒料C或D。以此类推，反复使用使用挤出机在230℃下加工得到的粒料，得到E或F，G或H，I或J。
表3
测试以上得到的粒料A、B、E、F、I、J的熔融指数。并将以上得到的粒料A、B、E、F、I、J在230℃下注塑成型，制作用于拉伸测试(GB1040.2-2006)的哑铃片，以及用于抗冲击测试(GB1043.1-2008)的样片，进行以下的评价。结果示于表4、表5、表6中。从上述结果可见，相比于TNPP，上述通式(1)表示的新型亚磷酸酯化合物的混合物可以有效降低热加工带来的聚合物降解，使得熔融指数上升幅度小，使得拉伸强度和抗冲击强度下降幅度小。
表4.热加工对熔融指数的影响
表5.热加工对拉伸强度的影响
表6.热加工对抗冲击强度的影响
| 配方1# | 配方2# | |
| 热加工一次后的抗冲击强度(kJ/m<sup>2</sup>) | 3.26 | 3.01 |
| 热加工三次后的抗冲击强度(kJ/m<sup>2</sup>) | 2.73 | 2.34 |
| 热加工五次后的抗冲击强度(kJ/m<sup>2</sup>) | 2.34 | 1.87 |
本说明书所述的内容仅仅是对发明构思实现形式的列举，本发明的保护范围不应当被视为仅限于实施例所陈述的具体形式。
Claims (7)
1.一种亚磷酸酯抗氧剂组合物，其特征在于包含具有腰果酚结构的下述通式(1)所示的亚磷酸酯抗氧剂化合物，
所述通式(1)中R表示氢原子、羟基、碳原子数1～30的烷基或碳原子数1～30的烷氧基，烷基、烷氧基任选被单个或多个氧原子或羰基中断；
所述通式(1)中n、m、k分别表示含单烯、双烯和三烯的腰果酚基团的个数，n、m、k均是大于等于0且小于等于3的整数，n、m与k三者之和为3。
2.如权利要求1所述的一种亚磷酸酯抗氧剂组合物，其特征在于所述通式(1)中R表示氢原子、羟基、碳原子数1～20的烷基或碳原子数1～20的烷氧基。
3.一种抗氧化性合成树脂组合物，其特征在于在合成树脂中混配有权利要求1的亚磷酸酯抗氧剂组合物。
4.如权利要求3所述的一种抗氧化性合成树脂组合物，其特征在于在合成树脂中混配的抗氧剂组合物，相对于抗氧剂组合物100质量份含有通式(1)所示的亚磷酸酯抗氧剂化合物10～100质量份，使含有质量分数10～100％的通式(1)所示的亚磷酸酯抗氧剂化合物的抗氧剂组合物配合于合成树脂中。
5.如权利要求4所述的一种抗氧化性合成树脂组合物，其特征在于相对于合成树脂100质量份，含有质量分数10～100％的通式(1)所示的亚磷酸酯抗氧剂化合物的抗氧剂组合物的混配量为0.01～20质量份，优选为0.01～10质量份。
6.如权利要求5所述的一种抗氧化性合成树脂组合物，其特征在于相对于合成树脂100质量份，含有质量分数10～100％的通式(1)所示的亚磷酸酯抗氧剂化合物的抗氧剂组合物的混配量为0.03～5质量份，优选为0.04～3质量份。
7.如权利要求3所述的一种抗氧化性合成树脂组合物，其特征在于合成树脂是聚氨酯树脂、聚酯树脂、聚烯烃树脂、含聚丁二烯段或聚戊二烯段的嵌段聚合物。
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