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CN110590849B - 一种含磷氮dopo衍生物阻燃剂及其制备方法和应用 - Google Patents

一种含磷氮dopo衍生物阻燃剂及其制备方法和应用 Download PDF

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CN110590849B
CN110590849B CN201910949224.XA CN201910949224A CN110590849B CN 110590849 B CN110590849 B CN 110590849B CN 201910949224 A CN201910949224 A CN 201910949224A CN 110590849 B CN110590849 B CN 110590849B
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马超
马世聪
周峰
胡伟兆
汪碧波
宋磊
胡源
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University of Science and Technology of China USTC
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Abstract

本发明公开了一种含磷氮DOPO衍生物阻燃剂及其制备方法和应用，其中含磷氮DOPO衍生物阻燃剂的结构通式为：
Figure DDA0002225021920000011
其中R1、R2、R3分别独立地选自氢、甲基、乙基、丙基、丁基、
Figure DDA0002225021920000012
Figure DDA0002225021920000013
R4选自乙基、丙基、丁基。本发明合成的阻燃剂分子结构中含有刚性较大的环状结构，热稳定性更好，并且同时含有磷和氮，共同发挥它们的阻燃作用，因此具有更好的阻燃效果。

Description

一种含磷氮DOPO衍生物阻燃剂及其制备方法和应用
技术领域
本发明属于阻燃剂制备技术领域，具体涉及一种含磷氮DOPO衍生物阻燃剂及其制备方法和应用。
背景技术
聚氨酯软泡广泛应用于车辆、家具等垫材以及内部装潢材料等，此类场合使用的材料均有较高的阻燃要求。但实际上，常规的聚氨酯软泡属易燃品，一旦引燃很难及时扑灭。如何提高聚氨酯软泡的阻燃性一直是这一领域的重点研究课题。目前常用的聚氨酯泡沫的阻燃剂可分为两大类：一是添加型阻燃剂，主要有磷酸三乙酯、甲基磷酸二甲酯(DMMP)、三(2-氯异丙基)磷酸酯(TCPP)、磷酸三氯乙酯(TCEP)、三聚氰胺、可膨胀石墨、氢氧化铝等。二是反应型阻燃剂，将阻燃元素磷、氮、卤素等通过化学键引入多元醇或异氰酸酯中，使聚氨酯泡沫材料具有永久阻燃性。
氮系阻燃剂因其毒性小、环境污染小、腐蚀性小和热分解温度高等特点，在阻燃领域的应用日趋广泛。其阻燃机理简述如下：氮系阻燃剂受热分解后，易放出氨气、氮气、氮氧化物等不燃性气体，不燃性气体的生成和阻燃剂的分解吸热会带走大部分的热量降低聚合物的表面温度。同时不燃性气体不仅起到稀释空气中氧气和高聚物受热分解产生的可燃性气体的作用，还能与空气中氧气反应生成氮气、水等物质，以此获得阻燃的效果。常用的氮系阻燃剂主要有三聚氰胺、双氰胺、胍盐等，但是氮系阻燃剂在单独添加时所需添加量较大，对于基体的机械性能产生较大的负面影响。故通常与磷系阻燃剂并用，利用磷-氮的协同效应，制备性能优异的阻燃剂。
DOPO是近年来科学家发现的新型含磷阻燃剂，DOPO及其衍生物的分子结构中含有刚性较大的联苯环结构和菲环结构，特别是侧面的含磷基团以环状O＝P-O键的方式接入，比一般的小分子型膦酸酯或未成环的有机膦酸酯热稳定性和化学稳定性更高。其阻燃机理简述如下：DOPO基阻燃剂在高分子材料燃烧时，可形成聚磷酸、亚磷酸、磷酸使材料表面脱水形成碳层，阻隔氧气和燃烧产生的热量向材料内部传递，实现凝聚相阻燃；同时，其在燃烧时产生的P·和PO·等自由基能够淬灭火焰中高活性的H·和HO·自由基，中断燃烧的链式反应，从而实现气相阻燃。DOPO中的P-H键经氧化后变P-OH，P-OH键可以与氨基反应生成P-O-·NH3 +-。利用这个反应可以合成DOPO衍生的盐类。
发明内容
本发明的目的是提供一种含磷氮DOPO衍生物阻燃剂及其制备方法和应用，制备这种阻燃剂所用的原料价廉易得，大部分低毒或无毒，反应过程采用水(和醇)作为溶剂，无副产物的生成和污染物的排放，因此具有很好的工业化应用前景。本发明合成的阻燃剂分子结构中含有刚性较大的环状结构，热稳定性更好，并且同时含有磷和氮，具有更好的阻燃效果。
本发明含磷氮DOPO衍生物阻燃剂，其结构通式为：
Figure BDA0002225021900000021
其中R1、R2、R3分别独立地选自氢、甲基、乙基、丙基、丁基、
Figure BDA0002225021900000022
Figure BDA0002225021900000023
R4选自乙基、丙基、丁基。
本发明含磷氮DOPO衍生物阻燃剂的制备方法，包括如下步骤：
步骤1：向DOPO中滴加过氧化氢溶液，滴加完成后在60-80℃下保温反应6-8小时，反应完成后过滤并用丙酮洗涤产物3-5次得到DOPO-OH；
步骤2：将DOPO-OH分散在溶剂中，超声后在室温条件下分批次向上述分散液中加入含胺物质，加入完成后升温至60-80℃保温反应4-6小时，反应完成后蒸干溶液，所得的糊状产物用去离子水洗涤3-5次，干燥后得到含磷氮DOPO衍生物。
步骤1中，所述过氧化氢溶液中H2O2与DOPO中磷原子的摩尔比2：1至5：1。
步骤2中，所述溶剂选自水或水和醇的混合溶液。所述醇选自甲醇、乙醇、丙醇、丁醇、戊醇等中的一种或多种，水和醇的体积比为1：1至5：1。
步骤2中，超声时间为1-3小时。
步骤2中，所述含胺物质选自氨气(氨水)、甲胺、乙胺、丙胺、丁胺、二甲胺、二乙胺、甲基乙胺、二丙胺、二丁胺、乙二胺、甲基乙二胺、乙基乙二胺、二甲基乙二胺、二乙基乙二胺、丙二胺、甲基丙二胺、乙基丙二胺、二甲基丙二胺、二乙基丙二胺、丁二胺、甲基丁二胺、乙基丁二胺、二甲基丁二胺、二乙基丁二胺、尿素、二氰二胺、三聚氰胺等中的一种或多种；DOPO-OH和含胺物质的摩尔比为1：1至1：3。
本发明反应过程如下：
第一步：DOPO中的P-H键被过氧化氢氧化为P-OH键。
Figure BDA0002225021900000031
第二步：氧化后的DOPO中P-OH与胺基反应。
Figure BDA0002225021900000032
其中R1、R2、R3分别独立地选自氢、甲基、乙基、丙基、丁基、
Figure BDA0002225021900000033
Figure BDA0002225021900000034
R4选自乙基、丙基、丁基。
本发明含磷氮DOPO衍生物阻燃剂的应用，是以所述含磷氮DOPO衍生物替代或部分替代常规通用的阻燃剂，用于制备阻燃聚合物。
所述聚合物包括聚氨酯、聚乙烯、聚丙烯等。
与现有技术相比，本发明的有益效果体现在：
1、所采用的原料价廉易得，反应步骤简单并且原料利用率高。反应条件温和，采用无毒溶剂水(和醇)，反应过程中没有副产物的生成和污染物的排放，因此具有很好的工业化应用前景。
2、本发明合成的阻燃剂分子结构中含有刚性较大的环状结构，热稳定性更好，并且同时含有磷和氮，共同发挥它们的阻燃作用，因此具有更好的阻燃效果。
附图说明
图1是实施例1制得的目标产物的核磁谱图(H谱和P谱)。
图2是实施例3制得的目标产物的核磁谱图(H谱和P谱)。
图3是实施例5制得的目标产物的核磁谱图(H谱和P谱)。
具体实施方式
下面以具体实施例作进一步说明，本发明中所用原料皆为市售。
实施例1：
1、在接有氮气和回流冷凝管的三口烧瓶中加入108g DOPO，随后升温至60℃，向三口烧瓶中缓慢滴入100mL的30％过氧化氢溶液，半小时内滴加完成后升温至80℃，继续反应8小时，然后撤去氮气，用丙酮洗涤产物3次，得到DOPO-OH。
2、向接有氮气和回流冷凝管的三口烧瓶中加入23.2g DOPO-OH和200mL(水与乙醇体积比1：1)溶液，在半小时内分批次加入9.0g二氰二胺，室温下反应半小时后升温至60℃，在60℃下保温反应8小时，然后撤去氮气，蒸干溶剂，目标产物的结构式为：
Figure BDA0002225021900000041
实施例2：
首先将20质量份实施例1中的含磷氮DOPO类衍生物、100质量份聚醚多元醇330、1.0质量份硅油、0.18质量份二月桂酸二丁基锡、0.25质量份A33和3.0质量份水混合均匀，然后加入41质量份TDI，高速搅拌后倒入模具中，发泡后放入60℃烘箱中熟化24小时，得到阻燃聚氨酯软泡。经测试，阻燃聚氨酯软泡氧指数为25.0％。添加20质量份常规阻燃剂甲基膦酸二甲酯(DMMP)，阻燃聚氨酯软泡的氧指数为22.0％。添加10份实施例1中的含磷氮DOPO类衍生物+10份DMMP，阻燃聚氨酯软泡的氧指数为24.0％。
实施例3：
1、DOPO-OH的合成按照实施例1中的步骤。
2、向接有氮气和回流冷凝管的三口烧瓶中加入23.2g DOPO-OH和200mL(水与乙醇体积比1：1)溶液，在半小时内分批次加入6.5g碳酰胺(尿素)，室温下反应半小时后升温至80℃，在回流状态下保温反应5小时；然后撤去氮气，蒸干溶剂，目标产物的结构式为：
Figure BDA0002225021900000051
实施例4：
首先将20质量份实施例3中的含磷氮DOPO类衍生物、100质量份聚醚多元醇330、1.0质量份硅油、0.23质量份二月桂酸二丁基锡、0.34质量份A33和3.0质量份水混合均匀，然后加入41质量份TDI，高速搅拌后倒入模具中，发泡后放入60℃烘箱中熟化24小时，得到阻燃聚氨酯软泡。经测试，阻燃聚氨酯软泡氧指数为24.5％。添加10份实施例3中的含磷氮DOPO类衍生物+10份DMMP，阻燃聚氨酯软泡的氧指数为23.5％。
实施例5：
1、DOPO-OH的合成按照实施例1中的步骤。
2、向接有氮气和回流冷凝管的三口烧瓶中加入23.2g DOPO-OH和200mL(水与乙醇体积比1：1)溶液，在半小时内分批次加入13.0g三聚氰胺，室温下反应半小时后升温至80℃，在回流状态下保温反应5小时；然后撤去氮气，蒸干溶剂，目标产物的结构式为：
Figure BDA0002225021900000061
实施例6：
首先将20质量份实施例5中的含磷氮DOPO类衍生物、100质量份聚醚多元醇330、1.0质量份硅油、0.18质量份二月桂酸二丁基锡、0.25质量份A33和3.0质量份水混合均匀，然后加入41质量份TDI，高速搅拌后倒入模具中，发泡后放入60℃烘箱中熟化24小时，得到阻燃聚氨酯软泡。经测试，阻燃聚氨酯软泡氧指数为24.0％。添加10份实施例5中的含磷氮DOPO类衍生物+10份DMMP，阻燃聚氨酯软泡的氧指数为23.0％。

Claims (3)

1.一种含磷氮DOPO衍生物阻燃剂，其特征在于其结构式为：
Figure FDA0003019260880000011
2.一种权利要求1所述的含磷氮DOPO衍生物阻燃剂的制备方法，其特征在于包括如下步骤：
步骤1：向DOPO中滴加过氧化氢溶液，滴加完成后在60-80℃下保温反应6-8小时，反应完成后过滤并用丙酮洗涤产物3-5次得到DOPO-OH；
步骤2：将23.2g DOPO-OH分散在溶剂中，超声后在室温条件下分批次向上述分散液中加入9.0g二氰二胺，加入完成后升温至60℃保温反应8小时，反应完成后蒸干溶液，所得的糊状产物用去离子水洗涤3-5次，干燥后得到含磷氮DOPO衍生物；
步骤1中，所述过氧化氢溶液中H2O2与DOPO中磷原子的摩尔比2：1至5：1；
步骤2中，所述溶剂为水和乙醇按体积比1：1构成的混合溶液。
3.一种权利要求1所述的含磷氮DOPO衍生物阻燃剂的应用，其特征在于：是以所述含磷氮DOPO衍生物替代或部分替代常规通用的阻燃剂，用于制备阻燃聚合物；所述聚合物包括聚氨酯软泡。
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