CN112812030B - 基于乙二胺四乙酸的支化聚酰胺环氧固化剂的合成方法 - Google Patents
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Abstract
本发明涉及基于乙二胺四乙酸的支化聚酰胺环氧固化剂的合成方法,以脂肪胺、芳香胺、乙二胺四乙酸和二环己基碳二亚胺为原料,通过酰胺化反应制得小分子支化聚酰胺,本发明制备聚酰胺固化剂的方法简便,使用二环己基碳二亚胺催化酰胺化反应,大幅降低了反应温度,使得反应能够在常温常压下进行。
Description
技术领域
本发明涉及固化剂制备技术领域,尤其是基于乙二胺四乙酸的支化聚酰胺环氧固化剂的合成方法。
背景技术
环氧树脂固化剂是环氧树脂应用技术范畴中极其重要的材料,也是决定环氧产品工艺技术和特征的关键组份。环氧树脂应用技术的发展与固化剂的结构、规格和质量密切相关,运用固化剂实现环氧树脂理想的应用效果是配方设计的主要任务。
直链多元胺是最简单也是品种最多的固化剂,其特点是此类固化剂一般可以在室温下与环氧树脂发生固化反应,但伯氨会与空气中的二氧化碳反应生成碳酸盐,严重影响涂装应用及固化物的性能,对于大面积施工会带来不利影响。为了解决以上问题,开发出了聚酰胺固化剂。聚酰胺固化剂也称之为低分子聚酰胺或聚酰胺多胺,通常采用亚麻油酸等二聚体酸与脂肪族多胺反应制得低分子量的聚酰胺化合物。聚酰胺固化剂的添加量允许范围较宽,且固化剂几乎无毒性,无挥发性,对皮肤刺激性也很小。其环氧树脂固化物的机械性能、电性能均衡,耐冲击性优良,尤其是粘结性很好。使用低分子聚酰胺固化的环氧树脂固化物具有较好的综合性能,因此也是多胺类固化剂的热点改性方法。
国内生产低分子聚酰胺的多元羧酸原料通常采用植物油脂肪酸二聚体,如桐油酸二聚体、亚麻油酸二体等,此类多元羧酸需在高温(300℃)下与多元伯胺反应,同时合成时往往需要高压环境,在实际生产时具有较大的安全风险。另外,虽然聚酰胺固化剂对环氧固化物具有较好增韧效果,但在高冲击强度的领域(如汽车、桥梁和钢架结构的涂层)的应用中依旧有提升的需求。因此发展生产工艺简单、抗冲击性能优异的聚酰胺固化剂是目前学术界和工业界的研究热点。
常规植物油脂肪酸二聚体的合成条件苛刻,需要高温高压;常规聚酰胺固化剂的分子为直链结构,对环氧固化物的增韧效果还可进一步提高。
发明内容
(一)要解决的技术问题
为了解决现有技术的上述问题,本发明提供基于乙二胺四乙酸的支化聚酰胺环氧固化剂的合成方法。
(二)技术方案
为了达到上述目的,本发明采用的主要技术方案包括:
基于乙二胺四乙酸的支化聚酰胺环氧固化剂的合成方法,以脂肪胺、芳香胺、乙二胺四乙酸和二环己基碳二亚胺为原料,通过酰胺化反应制得小分子支化聚酰胺,反应式如下:
具体合成步骤如下:
第一步,称取脂肪胺、芳香胺和二环己基碳二亚胺,送入混合反应器中,温度控制于30-50℃,在工业氮气保护下搅拌2分钟;
第二步,在30分钟内平均分三次加入乙二胺四乙酸并搅拌,使其慢慢溶解于体系中,保温3小时得到粘稠液体;
第三步,将第二步反应后得到粘稠液体滴入占粘稠液体10倍质量的冷四氢呋喃中,滤去废渣得滤液;
第四步,将滤液在30℃减压蒸馏除去四氢呋喃,即得支化聚酰胺环氧固化剂。
进一步地,所述脂肪胺:芳香胺:乙二胺四乙酸:二环己基碳二亚胺的摩尔比为3.0-5.0:1.0-1.6:1.0:4.2。
进一步地,所述脂肪胺为乙二胺、己二胺、二乙烯三胺或三乙烯四胺。
进一步地,所述芳香胺为间苯二甲胺、间苯二胺或二氨基二苯基甲烷。
(三)有益效果
本发明的有益效果是:1、本发明制备聚酰胺固化剂的方法简便,使用二环己基碳二亚胺(DCC)催化酰胺化反应,大幅降低了反应温度,使得反应能够在常温常压下进行。
2、乙二胺四乙酸是廉价易得、无毒无害的四官能度多元酸,可与多元胺制得支化聚酰胺化合物。
3、本发明制备的支化聚酰胺化合物克服了多元胺的高毒性,其酰胺以及支化结构有利于增加环氧树脂固化物柔韧性和粘接性,具有良好的综合性能。
具体实施方式
为了更好的解释本发明,以便于理解,下面通过具体实施方式,对本发明作详细描述。
基于乙二胺四乙酸的支化聚酰胺环氧固化剂的合成方法,以脂肪胺、芳香胺、乙二胺四乙酸(EDTA)和二环己基碳二亚胺(DCC)为原料,通过酰胺化反应制得小分子支化聚酰胺,反应式如下:
具体合成步骤如下:
第一步,称取脂肪胺、芳香胺和二环己基碳二亚胺,送入混合反应器中,温度控制于30-50℃,在工业氮气保护下搅拌2分钟;
第二步,在30分钟内平均分三次加入乙二胺四乙酸并搅拌,使其慢慢溶解于体系中,保温3小时得到粘稠液体;
第三步,将第二步反应后得到粘稠液体滴入占粘稠液体10倍质量的冷四氢呋喃(THF)中,放置在冰箱中一小时后滤去废渣得滤液;
第四步,将滤液在30℃减压蒸馏除去四氢呋喃,即得支化聚酰胺环氧固化剂。
进一步地,所述脂肪胺:芳香胺:乙二胺四乙酸(EDTA):二环己基碳二亚胺(DCC)的摩尔比为3.0-5.0:1.0-1.6:1.0:4.2。
进一步地,所述脂肪胺为乙二胺、己二胺、二乙烯三胺或三乙烯四胺。
进一步地,所述芳香胺为间苯二甲胺、间苯二胺或二氨基二苯基甲烷。
常规植物油二聚体合成的聚酰胺为线性聚合物;乙二胺四乙酸(EDTA)是廉价易得、无毒无害的四官能度多元酸,将其与二元胺反应可制得支化聚酰胺化合物;相对于线性聚合物而言,支化聚合物具有粘度低,官能度高,溶解性良好且无链缠结等特点,为环氧树脂的增韧改性提供了一种新的有效方法。
另外基于相似相容的原理,本发明在体系中引入部分芳香胺可增强固化剂组分与环氧树脂的相容性,提升固化物的硬度与强度。
实施例1
1.在200ml反应瓶中,装有搅拌器、温度计、加料口和通气管。投入三乙烯四胺29.20g、间苯二甲胺10.20g、二环己基碳二亚胺43.26g混合,氮气保护下40℃保温2分钟;
2.通过加料口缓慢加入乙二胺四乙酸14.60g,时间控制在30分钟;
3.反应3小时后得粘稠液体,取出后滴入500ml冷四氢呋喃(THF)中,在冰箱中放置1小时后滤去滤渣;
4.最后,将滤液在30℃减压蒸馏除去四氢呋喃,得45.24g黄色粘稠液体即支化聚酰胺环氧固化剂,收率89.7%(以乙二胺四乙酸为底物),胺值730mgKOH/g。
以上所述仅为本发明的较佳实施例,凡依本发明申请专利范围所做的均等变化与修饰,皆应属本发明的涵盖范围。
Claims (2)
1.基于乙二胺四乙酸的支化聚酰胺环氧固化剂的合成方法,其特征在于,以脂肪胺、芳香胺、乙二胺四乙酸和二环己基碳二亚胺为原料,通过酰胺化反应制得小分子支化聚酰胺,反应式如下:
;
具体合成步骤如下:
第一步,称取脂肪胺、芳香胺和二环己基碳二亚胺,送入混合反应器中,温度控制于30-50℃,在工业氮气保护下搅拌2分钟;
第二步,在30分钟内平均分三次加入乙二胺四乙酸并搅拌,使其慢慢溶解于体系中,保温3小时得到粘稠液体;
第三步,将第二步反应后得到粘稠液体滴入占粘稠液体10倍质量的冷四氢呋喃中,滤去废渣得滤液;
第四步,将滤液在30℃减压蒸馏除去四氢呋喃,即得支化聚酰胺环氧固化剂;
其中,所述脂肪胺为三乙烯四胺;所述芳香胺为间苯二甲胺。
2.如权利要求1所述的基于乙二胺四乙酸的支化聚酰胺环氧固化剂的合成方法,其特征在于,所述脂肪胺:芳香胺:乙二胺四乙酸:二环己基碳二亚胺的摩尔比为3.0-5.0:1.0-1.6:1.0:4.2。
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