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CN111763151B - 一种高防腐性能腰果酚改性多元胺固化剂的制备方法 - Google Patents

一种高防腐性能腰果酚改性多元胺固化剂的制备方法 Download PDF

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CN111763151B
CN111763151B CN202010602702.2A CN202010602702A CN111763151B CN 111763151 B CN111763151 B CN 111763151B CN 202010602702 A CN202010602702 A CN 202010602702A CN 111763151 B CN111763151 B CN 111763151B
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cardanol
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modified polyamine
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CN111763151A (zh
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王秋伟
顾奇
李旭锋
陈建
吕云兴
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Zhejiang Wansheng Co ltd
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Abstract

本发明公开了一种腰果酚改性多元胺固化剂的制备方法，它将腰果酚、多聚甲醛和胺类化合物进行曼尼希反应，反应结束后加入水溶性引发剂进行聚合反应，反应结束后减压蒸除水分及过量的胺类化合物，得到腰果酚改性多元胺固化剂，固化剂与环氧树脂固化得到的涂料耐化学、耐腐蚀性能有很大的提高，表明本发明采用水溶性引发剂能够使很好烯烃聚合，聚合后分子明显的加强，从而使耐化学、耐腐蚀性能大大的提高。

Description

一种高防腐性能腰果酚改性多元胺固化剂的制备方法
技术领域
本发明涉及有机合成技术领域，具体涉及高防腐性能腰果酚改性多元胺固化剂的制备方法。
背景技术
腰果酚(Cardanol)是从腰果壳中提取出来的，具有酚羟基的结构，可替代部分酚类化合物参与化学反应，是一种具有可再生的生物资源，能解决部分石油能源危机。
由于腰果酚具有可再生性，利用腰果酚开发应用很多的产品，在腰果酚的应用中主要是腰果酚固化剂的制备，制备出的固化剂与环氧树脂进行固化，得到具有稳定性高、耐高温、低温下很好操作的漆膜，主要应用在轮船，集装箱上漆膜的涂层。
如中国专利：CN101333286，采用腰果酚，甲醛，多元胺进行反应，反应后进行减压脱水，得到腰果酚改性胺固化剂，而这种固化剂分子中主要是单分子的化合物，链上的分子双键很不稳定，防腐性能很差，长时间光照的条件下涂料很容易变成黄色，影响漆膜的外观。
中国专利CN107973899，通过采用添加腰果酚甘油醚、腰果酚一起与甲醛、多元胺进行反应，来改变产品的性能，如改善产品的颜色，硬度等，该专利没有根本上解决产品的颜色、耐化学防腐性能问题。
发明内容
针对现有技术中存在的上述问题，本发明的目的在于提供一种高防腐性能腰果酚改性多元胺固化剂的制备方法。
所述的一种高防腐性能腰果酚改性多元胺固化剂的制备方法，其特征在于将腰果酚、多聚甲醛和胺类化合物进行曼尼希反应，反应速度后加入水溶性引发剂进行聚合反应，反应结束后减压蒸除水分及过量的胺类化合物，得到高防腐性能腰果酚改性多元胺，
Figure GDA0003289552130000021
所述的高防腐性能腰果酚改性多元胺固化剂的制备方法，其特征在于腰果酚、多聚甲醛、胺类化合物的摩尔比为1:1-2:1.05-2。
所述的高防腐性能腰果酚改性多元胺固化剂的制备方法，其特征在于胺类化合物为脂肪胺、脂环胺或芳香胺。
所述的高防腐性能腰果酚改性多元胺固化剂的制备方法，其特征在于胺类化合物为乙二胺、二乙烯三胺、三乙烯四胺、四乙烯五胺中的一种或两种混合物。
所述的高防腐性能腰果酚改性多元胺固化剂的制备方法，其特征在于曼尼希反应温度为30-85℃。
所述的高防腐性能腰果酚改性多元胺固化剂的制备方法，其特征在于聚合反应温度为70-100℃，聚合时间为3-5小时。
所述的高防腐性能腰果酚改性多元胺固化剂的制备方法，其特征在于水溶性引发剂为偶氮二异丁脒盐酸盐、偶氮二异丁咪唑啉盐酸或偶氮异丁氰甲酰胺，水溶性引发剂的投料量为腰果酚质量的1-5％。
所述的高防腐性能腰果酚改性多元胺固化剂的制备方法，其特征在于反应后减压蒸馏除水份的温度为50-90℃，真空度为10-50KPa。
所述的高防腐性能腰果酚改性多元胺固化剂的制备方法，其特征在于按投料比，将腰果酚和多聚甲醛加入反应器中，室温缓慢滴加乙二胺，控制滴加时的温度为50-80℃，滴加时间为2-2.5小时，滴完在75-80℃保温3.5-4.5小时，保温结束后加入水溶性引发剂控制温度在95-100℃回流反应4-5小时，反应后降低温度至温度80-85℃，在真空度为10～15KPa下蒸馏脱水，得到红棕色溶液高防腐性能腰果酚改性多元胺固化剂。
通过采用上述技术，与现有技术相比，本发明的有益效果如下：
1)本发明通过采用化学聚合的方法改变腰果酚改性多元胺本身的特性，大大提高了其稳定性，高分子量的化合物比单分子链化合物稳定，稳定的具体表现在耐化学防腐性能高等，从根本上改变产品的性能，减少小分子化合的量；
2)本发明的腰果酚改性多元胺的制备方法，在曼尼希反应后，用水溶性引发剂引发直接进行聚合反应，不需要进行特别的处理，避免很多引发剂容易遇水分解、使得聚合的反应条件苛刻的问题，且其重复性好、操作简单、能够稳定工业化生产固化剂的原料；
3)本发明通过将所得的聚合高分子量的化合物与环氧树脂进行复配，得到一种新型固化剂，由于将腰果酚中的支链烯烃键通过聚合反应，使得较小的分子变成聚合分子量更大的化合物，提高其稳定性，因此能使得到的固化剂具有耐化学防腐性能高，抗长时间光照射变黄的现象。
具体实施方式
以下实施例用于说明本发明，但不用来限制本发明的范围。
实施例1
腰果酚1500kg，多聚甲醛300kg，投入反应釜中，室温开始滴加乙二胺450kg，滴加过程控制滴加速度，升温明显，温度在50-80℃，滴加时间大约2小时，滴加完在75-80℃保温4小时，保温后加入偶氮二异丁脒盐酸盐15kg控制温度在95-100℃回流反应4-5小时，反应后降低温度脱至温度80-85℃，真空度为：10～15KPa，脱水后为红棕色溶液，胺值/(mgKOH/g)＝305,黏度/mpa.S＝25080。
对比例1：
腰果酚1500kg，多聚甲醛300kg，投入反应釜中，室温开始滴加乙二胺450kg，控制温度在50-80℃，滴加时间大约2小时，滴加完在75-80℃保温4小时，反应后降低温度脱至温度80-100℃，真空度为：10～15KPa，脱水后为红棕色溶液，胺值/(mgKOH/g)＝310,黏度/mpa.S＝800。
实施例2
腰果酚1500kg，多聚甲醛305kg，加入反应釜中，室温开始滴加乙二胺450kg，控制温度在75-80℃，滴加时间大约2小时，滴加完在75-80℃保温4小时，保温后加入偶氮二异丁脒盐酸盐20kg控制温度在95-100℃回流反应4-5小时，反应后降低温度脱至温度85-90℃，真空度为：15～20KPa，脱水后为红棕色溶液，胺值/(mgKOH/g)＝308,黏度/mpa.S＝28100。
实施例3
腰果酚3000kg，多聚甲醛600kg，加入反应釜中，室温开始滴加乙二胺901kg，控制温度在75-80℃，滴加时间大约4小时，滴加完在75-80℃保温5小时，保温后加入偶氮二异丁脒盐酸盐30kg控制温度在95-100℃回流反应4-5小时，反应后降低温度慢慢脱至温度80-90℃，真空度为：15～20KPa，脱水后为红棕色溶液，胺值/(mgKOH/g)＝300,黏度/mpa.S＝29400。
实施例4
腰果酚1500kg，多聚甲醛300kg，加入反应釜中，室温开始滴加乙二胺450kg，控制温度在75-80℃，滴加时间大约3小时，滴加完在75-80℃保温5小时，保温后加入偶氮二异丁咪唑啉盐酸15kg控制温度在95-100℃回流反应4-5小时，反应后降低温度慢慢脱至温度75-80℃，真空度为：10～15KPa，脱水后为红棕色溶液，胺值/(mgKOH/g)＝320,黏度/mpa.S＝28300。
实施例5
腰果酚1500kg，多聚甲醛290kg，加入反应釜中，室温开始滴加乙二胺450kg，控制温度在75-80℃，滴加时间大约3小时，滴加完在75-80℃保温5小时，保温后加入偶氮异丁氰甲酰胺15kg控制温度在95-100℃回流反应4-5小时，反应后降低温度慢慢脱至温度75-80℃，真空度为：10～15KPa，脱水后为红棕色溶液，胺值/(mgKOH/g)＝318,黏度/mpa.S＝32800。
性能测试：
用实例1-5的样品与环氧树脂E51采用常规技术进行固化反应，环氧树脂：固化剂的比例为100：30，按照涂料测试国家标准进行检测，检测结果如表1所示：
表1实例1-5的样品与环氧树脂E51反应后产品性能表
Figure GDA0003289552130000061
其他性能测试如表2所示：
表2实例1-5的样品与环氧树脂E51反应后产品性能表
Figure GDA0003289552130000071
从上述表1可以看出，本发明得到的高防腐性能腰果酚改性多元胺固化剂与环氧树脂固化后，得到的涂料其耐化学、耐腐蚀性能很大的提高。表1的结果表明采用水溶性引发剂能够很好使烯烃聚合，聚合后分子明显的加强，耐化学、耐腐蚀性能大大的提高，较没有聚合前有明显的变化，聚合后的黏度/mpa.S＝28300左右，没有聚合的前的黏度/mpa.S＝800左右，产品的结构组成明显的发生变化，必然引起性能的改变。
从上述表2可以看出，本发明改进后的固化剂冲击性能反冲50cm,正常，而对照例漆膜破裂很严重，干燥时间明显的提高，大大加深了固化剂的应用范围。
虽然，上文中已经用一般性说明、具体实施方式及试验，对本发明作了详尽的描述，但在本发明基础上，可以对之作一些修改或改进，这对本领域技术人员而言是显而易见的。因此，在不偏离本发明精神的基础上所做的这些修改或改进，均属于本发明要求保护的范围。

Claims (5)

1.一种腰果酚改性多元胺固化剂的制备方法，其特征在于将腰果酚、多聚甲醛和胺类化合物进行曼尼希反应，反应结束后加入水溶性引发剂进行烯烃聚合反应，反应结束后减压蒸除水分及过量的胺类化合物，得到腰果酚改性多元胺，所述聚合反应温度为70-100℃，聚合时间为3-5小时；所述水溶性引发剂为偶氮二异丁脒盐酸盐、偶氮二异丁咪唑啉盐酸或偶氮异丁氰甲酰胺，水溶性引发剂的投料量为腰果酚质量的1-5%；所述胺类化合物为乙二胺，
所述腰果酚的结构式如下所示：
Figure DEST_PATH_IMAGE002
。
2.根据权利要求1所述的腰果酚改性多元胺固化剂的制备方法，其特征在于腰果酚、多聚甲醛、胺类化合物的摩尔比为1:1-2:1.05-2。
3.根据权利要求1所述的腰果酚改性多元胺固化剂的制备方法，其特征在于曼尼希反应温度为30-85℃。
4.根据权利要求1所述的腰果酚改性多元胺固化剂的制备方法，其特征在于反应后减压蒸馏除水份的温度为50-90℃，真空度为10-50KPa。
5.根据权利要求1-4任一所述的腰果酚改性多元胺固化剂的制备方法，其特征在于按投料比，将腰果酚和多聚甲醛加入反应器中，室温下缓慢滴加乙二胺，控制滴加时的温度为50-80℃，滴加时间为2-2.5小时，滴完后于75-80℃保温3.5-4.5小时，保温结束后加入水溶性引发剂控制温度在95-100℃回流反应4-5小时，反应后降温至80-85℃，在真空度为10～15KPa下蒸馏脱水，得到红棕色溶液即为腰果酚改性多元胺固化剂。
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