CN109232977B - 一种含有活性基团的磷杂菲衍生物阻燃剂及其制备方法 - Google Patents
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Abstract
本发明公开了一种含有活性基团的磷杂菲衍生物阻燃剂，简称为ABD，ABD的结构式如下，其合成方法是：在有机溶剂体系中采用丙烯醛(Acrolein)和9,10‑二氢‑9‑氧杂‑10‑磷杂菲‑10‑氧化物(DOPO)为原料，0‑20℃条件下反应，在有机溶剂中实现DOPO中的P‑H键与丙烯醛中的醛基和双键同时进行加成反应，脱除溶剂后并通过热水洗涤提纯，分离出产物，烘干后获得ABD化合物。
Description
技术领域
本发明涉及一种含有活性基团的磷杂菲衍生物阻燃剂及其制备方法，是一种新型的磷杂菲衍生物阻燃剂，属于利用化学合成方法制备阻燃助剂的技术领域。
背景技术
近些年来，磷杂菲DOPO化合物由于其优异的阻燃性能和改变分子的物理性质在环氧树脂中得到广泛应用。磷杂菲DOPO的衍生物比如DOPO-HQ、2DOPO-2NH2、2DOPO-2PhOH、DOPO-ITA、DOPO-MA等化合物也被陆续开发,并应用在环氧树脂中，赋予了环氧树脂优异的阻燃性能和物理性能。
在《新型阻燃剂制造与应用》中提到磷杂菲衍生物2DOPO-2NH2、2DOPO-2PhOH，其合成方法是DOPO中的P-H键与羰基加成后的产物。在《新型阻燃剂制造与应用》中提到磷杂菲衍生物DOPO-MA、DOPO-ITA，其合成方法是DOPO中的P-H键与双键加成后的产物。
本发明的磷杂菲衍生物，制备方法简单，不需要在加热条件下即可反应，且只需要一步反应，0-20℃时，DOPO中的P-H键即可与丙烯醛中的双键和醛基同时进行加成反应，反应速率快，无副产物，产率高，提纯方法简单，获得产物还含有可活性基团，化学结构中磷含量更高。
发明内容
本发明采用丙烯醛(Acrolein)和9,10-二氢-9-氧杂-10-磷杂菲-10-氧化物(DOPO)为原料，通过DOPO中的P-H键与丙烯醛中的醛基和双键同时进行加成反应，制备的一种含有活性基团的磷杂菲衍生物，简称为ABD。
ABD分子式如下：
ABD的制备采用丙烯醛(Acrolein)和9,10-二氢-9-氧杂-10-磷杂菲-10-氧化物(DOPO)为原料，在有机溶剂中反应,通过蒸馏方法除去有机溶剂获得ABD粗产物，并将ABD在70-100℃热水中洗涤提纯，获得ABD产物。
所用合成原料：丙烯醛、9,10-二氢-9-氧杂-10-磷杂菲-10-氧化物；有机溶剂包括：四氢呋喃、甲苯、二甲苯、氯仿、乙二醚、丙酮。
合成工艺
在有机溶剂体系中：将丙烯醛和9,10-二氢-9-氧杂-10-磷杂菲-10-氧化物按照一定的比例加入到有机溶剂中，其中丙烯醛和9,10-二氢-9-氧杂-10-磷杂菲-10-氧化物的摩尔比为1:2.0-1:4.0，有机溶剂的质量为所用9,10-二氢-9-氧杂-10-磷杂菲-10-氧化物质量的4-8倍，反应温度在0-20℃，搅拌条件下反应1-3小时，有机溶剂为四氢呋喃、甲苯、二甲苯、氯仿、乙二醚、丙酮中的一种，通过蒸馏方法除去有机溶剂获得ABD粗产物。
将ABD粗产物加入到热水中，保持温度在70-100℃，搅拌洗涤，通过分液漏斗等方法分离出产物，烘干后获得产物ABD，产率在99％以上，纯度98％以上。
有益效果
(1)本发明的含有活性基团的磷杂菲衍生物，其结构与磷杂菲衍生物2DOPO-2NH2、DOPO-MA相比，结构中磷含量更高；与磷杂菲衍生物DOPO-MA相比，还含有一个活性基团羟基，可以作为一种聚氨酯的反应性阻燃剂；
(2)本发明的含有活性基团的磷杂菲衍生物，制备方法简单，不需要在加热条件下即可反应，且只需要一步反应，0-20℃时，DOPO中的P-H键即可与丙烯醛中的双键和醛基同时进行加成反应，反应速率快，无副产物，产率高，且提纯方法简单，处理效率高，有效降低了成本，有利于产业化放大生产。
附图说明
附图1制得的ABD的核磁氢谱图；
附图2制得的ABD的红外谱图。
具体实施方式
实施例1
将5.6g(0.1mol)丙烯醛(Acrolein)和43.2g(0.2mol)9,10-二氢-9-氧杂-10-磷杂菲-10-氧化物(DOPO)加入到装有175二甲苯的三口烧瓶中，在室温条件下，温度为0℃时，快速搅拌，反应3小时，反应结束后，减压蒸馏，除去二甲苯，在三口烧瓶中加入热水，保持温度70℃，通过分液漏斗分离出产物，烘干后，得到产物，经与标准谱图比对，即为目标产物，产率99％，纯度99.5％。
实施例2
将5.6g(0.1mol)丙烯醛(Acrolein)和54g(0.25mol)9,10-二氢-9-氧杂-10-磷杂菲-10-氧化物(DOPO)加入到装有270g四氢呋喃的三口烧瓶中，在室温条件下，温度为5℃时，快速搅拌，反应2小时，反应结束后，常压蒸馏，除去四氢呋喃，在三口烧瓶中加入热水，保持温度80℃，通过分液漏斗分离出产物，烘干后，得到产物，经与标准谱图比对，即为目标产物，产率99.5％，纯度99％。
实施例3
将5.6g(0.1mol)丙烯醛(Acrolein)和64.8g(0.3mol)9,10-二氢-9-氧杂-10-磷杂菲-10-氧化物(DOPO)加入到装有380g氯仿的三口烧瓶中，在室温条件下，温度为15℃时，快速搅拌，反应1小时，反应结束后，减压蒸馏，除去氯仿，在三口烧瓶中加入热水，保持温度90℃，通过分液漏斗分离出产物，烘干后，得到产物，经与标准谱图比对，即为目标产物，产率99.7％，纯度98.5％。
实施例4
将5.6g(0.1mol)丙烯醛(Acrolein)和86.4g(0.4mol)9,10-二氢-9-氧杂-10-磷杂菲-10-氧化物(DOPO)加入到装有690g丙酮的三口烧瓶中，在室温条件下，温度为20℃时，快速搅拌，反应1小时，反应结束后，减压蒸馏，除去丙酮，在三口烧瓶中加入热水，保持温度100℃，通过分液漏斗分离出产物，烘干后，得到产物，经与标准谱图比对，即为目标产物，产率99.8％，纯度98％。
Claims (4)
1.一种含有活性基团的磷杂菲衍生物阻燃剂的制备方法，其特征在于，所述阻燃剂的分子结构式为：
该方法是：在有机溶剂中将丙烯醛(Acrolein)和9,10-二氢-9-氧杂-10-磷杂菲-10-氧化物(DOPO)搅拌混合在0-20℃下反应1-3小时，脱除溶剂后得到ABD粗产物；再将粗产物加入到热水中，保持温度在70-100℃，洗涤、分离，烘干后获得ABD。
2.根据权利要求1所述的含有活性基团的磷杂菲衍生物阻燃剂的制备方法，其特征在于，所述的丙烯醛和9,10-二氢-9-氧杂-10-磷杂菲-10-氧化物的摩尔比为1:2.0-1:4.0。
3.根据权利要求1所述的含有活性基团的磷杂菲衍生物阻燃剂的制备方法，其特征在于，所述的有机溶剂的质量为所用9,10-二氢-9-氧杂-10-磷杂菲-10-氧化物质量的4-8倍。
4.根据权利要求1所述的含有活性基团的磷杂菲衍生物阻燃剂的制备方法，其特征在于，所述的有机溶剂为四氢呋喃、甲苯、二甲苯、氯仿、乙二醚、丙酮中的一种。
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| "基于DOPO的阻燃剂合成及其对不同高分子材料的阻燃效率";Christoph Klinkowski等;《中国材料进展》;20130331;第32卷(第3期);144-154页 * |
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