CN105440080A - 一种含磷丙烯酸酯的制备方法 - Google Patents
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Abstract
一种含磷丙烯酸酯的制备方法,其配方为:2-甲基-3-(6-氧代-6H-二苯并[c,e][1,2]氧磷杂己环-6-基)丙酸2-羟乙酯13.88%~18.58%,丙烯酰氯3.56%~4.79%,二氯甲烷71.14%~78.94%,三乙胺4.79%~5.68%;其制备步骤为:向反应容器中加入配方量的2-甲基-3-(6-氧代-6H-二苯并[c,e][1,2]氧磷杂己环-6-基)丙酸2-羟乙酯和二氯甲烷,将装置浸入冰浴,当体系温度降低至-5℃时,加入配方量的三乙胺;保持-5℃30min,将丙烯酰氯缓慢的滴加至装置内,滴加完毕后,保持反应温度0~-5℃2h;然后将体系升温至25℃,反应10h后出料,用去离子水洗涤至pH值为7,得到产物。
Description
技术领域
本发明涉及一种含磷丙烯酸酯及其制备方法,属于高分子化学及聚合物技术的技术领域。
背景技术
含卤阻燃剂由于在燃烧的过程中释放有毒气体而使得其应用受到限制。磷元素阻燃剂阻燃效率高,磷系化合物结构多样,且通常燃烧后不会释放有毒物质,因此,磷元素阻燃收到人们的青睐。
拥有活性官能团使阻燃元素以化学键的方式引入到分子链中去,这样既可以提升基材聚合物的阻燃性能和热性能,同时又可以降低阻燃元素对于材料本身的损害。合成成本低廉,工艺简单的活性阻燃剂成为技术领域的重点。
CN103073746A公开了一种含DOPO和活性双键的反应型含磷阻燃剂及其制备方法和应用。该发明以二氯取代磷酸酯与丙烯酸化或部分甲基丙烯酸化的多元醇或多元酚反应,然后再与DOPO改性的芳香基二元酚或DOPO改性的芳香基二元醇反应,得到同时具有活性双键和DOPO阻燃基团的可固化的反应型阻燃单体分子。当用于环氧丙烯酸树脂和不饱和聚酯树脂的阻燃时,能够显著提高树脂的极限氧指数LOI值,阻燃效果很好。然而此阻燃剂合成成本较高,合成工艺较为复杂,本发明利用相对廉价原料,得到含双键磷阻燃剂。
发明内容
本发明目的是提供一种含磷丙烯酸酯的制备方法。
本发明是一种含磷丙烯酸酯的制备方法,按质量百分数计,其配方为:
2-甲基-3-(6-氧代-6H-二苯并[c,e][1,2]氧磷杂己环-6-基)丙酸2-羟乙酯13.88%~18.58%,丙烯酰氯3.56%~4.79%,二氯甲烷71.14%~78.94%,三乙胺4.79%~5.68%;
其制备步骤为:向反应容器中加入配方量的2-甲基-3-(6-氧代-6H-二苯并[c,e][1,2]氧磷杂己环-6-基)丙酸2-羟乙酯和二氯甲烷,将装置浸入冰浴,当体系温度降低至-5℃时,加入配方量的三乙胺;保持-5℃30min,将丙烯酰氯缓慢的滴加至装置内,滴加过程中保持温度维持在0~-5℃;滴加完毕后,保持反应温度0~-5℃2h;然后将体系升温至25℃,反应10h后出料,用去离子水洗涤至pH值为7,最后进行结晶,得到产物。
本发明的有益之处为:合成了新的含磷丙烯酸酯单体,可用于自由基共聚合成本体阻燃丙烯酸树脂,也可以作为反应型阻燃剂添加到聚合物材料中起到阻燃作用,合成工艺简单。
具体实施方式
本发明是一种含磷丙烯酸酯的制备方法,按质量百分数计,其配方为:
2-甲基-3-(6-氧代-6H-二苯并[c,e][1,2]氧磷杂己环-6-基)丙酸2-羟乙酯13.88%~18.58%,丙烯酰氯3.56%~4.79%,二氯甲烷71.14%~78.94%,三乙胺4.79%~5.68%;
其制备步骤为:向反应容器中加入配方量的2-甲基-3-(6-氧代-6H-二苯并[c,e][1,2]氧磷杂己环-6-基)丙酸2-羟乙酯和二氯甲烷,将装置浸入冰浴,当体系温度降低至-5℃时,加入配方量的三乙胺;保持-5℃30min,将丙烯酰氯缓慢的滴加至装置内,滴加过程中保持温度维持在0~-5℃;滴加完毕后,保持反应温度0~-5℃2h;然后将体系升温至25℃,反应10h后出料,用去离子水洗涤至pH值为7,最后进行结晶,得到产物。
根据以上所述的含磷丙烯酸酯的制备方法,按质量百分数计,合成2-甲基-3-(6-氧代-6H-二苯并[c,e][1,2]氧磷杂己环-6-基)丙酸2-羟乙酯的配方为:
9,10-二氢-9-氧杂-10-磷杂菲-10-氧化物22.88%~27.34%,甲基丙烯酸羟乙酯20.66%~24.68%,甲苯51.42%~55.30%,三乙胺0%~1.17%;
其制备步骤为:在装有搅拌器、温度计、回流冷凝管的反应器中,加入配方量的甲苯和9,10-二氢-9-氧杂-10-磷杂菲-10-氧化物,搅拌加热,温度为84℃时9,10-二氢-9-氧杂-10-磷杂菲-10-氧化物全部溶解,然后向体系内滴加甲基丙烯酸羟乙酯和配方量的三乙胺,滴加结束后开始升温至120℃出现回流;待温度稳定后继续反应24h,体系变成乳白浑浊,停止反应,并冷却至25℃,分离得到下层粘稠液体;用甲苯多次洗涤后,在120℃温度下干燥48h,冷却至25℃得乳白色结晶固体。
根据以上所述的含磷丙烯酸酯的制备方法,三乙胺为缚酸剂。
本发明通过分子设计首先采用9,10-二氢-9-氧杂-10-磷杂菲-10-氧化物(DOPO)和甲基丙烯酸羟乙酯(HEMA)以1:1.5的物质的量之比反应得到2-甲基-3-(6-氧代-6H-二苯并[c,e][1,2]氧磷杂己环-6-基)丙酸2-羟乙酯(DOPO-HM)。然后DOPO-HM与丙烯酸氯以1:1.05的物质的量反应的到含双键磷阻燃剂DOPO-HM-DC。
含磷阻燃剂合成工艺路线如下:
基于制备含磷阻燃剂DOPO-HM的总质量,按质量百分数计,DOPO-HM的合成配方为:
DOPO22.88%~27.34%,甲基丙烯酸羟乙酯20.66%~24.68%,甲苯51.42%~55.30%,阻聚剂0%~1.17%。
DOPO-HM的制备步骤为:
在装有搅拌器、温度计、回流冷凝管的反应器中,加入配方量的甲苯和9,10-二氢-9-氧杂-10-磷杂菲-10-氧化物,搅拌加热,温度为84℃时9,10-二氢-9-氧杂-10-磷杂菲-10-氧化物全部溶解,然后向体系内滴加甲基丙烯酸羟乙酯和配方量的三乙胺,滴加结束后开始升温至120℃出现回流;待温度稳定后继续反应24h,体系变成乳白浑浊,停止反应,并冷却至25℃,分离得到下层粘稠液体;用甲苯多次洗涤后,在120℃温度下干燥48h,冷却至25℃得乳白色结晶固体。
基于含磷丙烯酸酯2-(2-甲基3-(6-氧-6H-二苯并[c,e][1,2]氧膦-6-基)丙酰氧基)丙烯酸乙酯的总质量,按重量份计,合成阻燃剂的配方为:
DOPO-HM14.46%~18.58%,丙烯酰氯3.73%~4.79%,二氯甲烷71.14%~78.94%,三乙胺4.27%~5.68%。
阻燃剂DOPO-HM-DC的制备步骤为:
向反应容器中加入配方量的2-甲基-3-(6-氧代-6H-二苯并[c,e][1,2]氧磷杂己环-6-基)丙酸2-羟乙酯和二氯甲烷,将装置浸入冰浴,当体系温度降低至-5℃时,加入配方量的三乙胺;保持-5℃30min,将丙烯酰氯缓慢的加入装置内,滴加过程中保持温度维持在0~-5℃;滴加完毕后,保持反应温度0~-5℃2h;然后将体系升温至25℃,反应10h后出料,用去离子水洗涤至pH值为7,最后进行结晶,得到产物。
以下是本发明的实施例,但本发明不局限于下列实施例中。
实施例1.
在装有搅拌器、温度计、回流冷凝管的反应器中,加入43.50kg甲苯和21.60kgDOPO搅拌加热。温度为85℃时DOPO完全溶解,然后开始滴加19.50kg甲基丙烯酸羟乙酯。滴加完毕后升温至120℃,体系出现回流,同时体系由清澈开始转变为浑浊。然后保温24h,出料。趁热用大量甲苯洗涤沉淀物,过滤。然后将产物在120℃下保温48h。得到乳白固体
实施例2.
将17.30kgDOPO-HM和66.25kg二氯甲烷加入到反应器中,机械搅拌30min。将体系降温至-5℃,加入5.11kg三乙胺,保持温度并搅拌30min,开始缓慢加入4.46kg丙烯酰氯和26.50kg二氯甲烷混合溶液。滴加结束后保持低温2h。然后将体系升温至25℃,反应10h后出料,用去离子水洗涤至有机相的pH值至7,最后进行结晶,得到产物。
Claims (3)
1.一种含磷丙烯酸酯的制备方法,按质量百分数计,其配方为:
2-甲基-3-(6-氧代-6H-二苯并[c,e][1,2]氧磷杂己环-6-基)丙酸2-羟乙酯13.88%~18.58%,丙烯酰氯3.56%~4.79%,二氯甲烷71.14%~78.94%,三乙胺4.79%~5.68%;
其制备步骤为:向反应容器中加入配方量的2-甲基-3-(6-氧代-6H-二苯并[c,e][1,2]氧磷杂己环-6-基)丙酸2-羟乙酯和二氯甲烷,将装置浸入冰浴,当体系温度降低至-5℃时,加入配方量的三乙胺;保持-5℃30min,将丙烯酰氯缓慢的滴加至装置内,滴加过程中保持温度维持在0~-5℃;滴加完毕后,保持反应温度0~-5℃2h;然后将体系升温至25℃,反应10h后出料,用去离子水洗涤至pH值为7,最后进行结晶,得到产物。
2.根据权利要求1所述的含磷丙烯酸酯的制备方法,其特征在于:按质量百分数计,合成2-甲基-3-(6-氧代-6H-二苯并[c,e][1,2]氧磷杂己环-6-基)丙酸2-羟乙酯的配方为:
9,10-二氢-9-氧杂-10-磷杂菲-10-氧化物22.88%~27.34%,甲基丙烯酸羟乙酯20.66%~24.68%,甲苯51.42%~55.30%,三乙胺0%~1.17%;
其制备步骤为:在装有搅拌器、温度计、回流冷凝管的反应器中,加入配方量的甲苯和9,10-二氢-9-氧杂-10-磷杂菲-10-氧化物,搅拌加热,温度为84℃时9,10-二氢-9-氧杂-10-磷杂菲-10-氧化物全部溶解,然后向体系内滴加甲基丙烯酸羟乙酯和配方量的三乙胺,滴加结束后开始升温至120℃出现回流;待温度稳定后继续反应24h,体系变成乳白浑浊,停止反应,并冷却至25℃,分离得到下层粘稠液体;用甲苯多次洗涤后,在120℃温度下干燥48h,冷却至25℃得乳白色结晶固体。
3.根据权利要求1所述的含磷丙烯酸酯的制备方法,其特征在于三乙胺为缚酸剂。
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