CN110698649B - 一种抗紫外阻燃型环氧树脂固化剂及其制备 - Google Patents
一种抗紫外阻燃型环氧树脂固化剂及其制备 Download PDFInfo
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Abstract
本发明属于环氧树脂材料技术领域,具体涉及一种抗紫外阻燃型环氧树脂固化剂及其制备,本发明提供的抗紫外阻燃型环氧树脂固化剂,结构如式(I)所示,所述固化剂含有的紫外吸收活性基团和阻燃活性基团参与环氧树脂的固化反应,均匀地将紫外吸收元素和阻燃元素引入环氧树脂链中,大大地提高了环氧树脂的使用性能。
Description
技术领域
本发明属于环氧树脂材料技术领域,具体涉及一种抗紫外阻燃型环氧树脂固化剂及其制备。
技术背景
环氧树脂是一种重要的热固性树脂,以优异的力学性能,电性能和粘结性能著称,广泛的应用于电子电器、化工防腐、航空航天、玻璃钢复合材料制备等领域,并越来越受到人们的重视。但是,环氧树脂光环境下易老化、易燃性等缺点也成为了限制其广泛应用的主要瓶颈。因此,提高环氧树脂的抗紫外性能、阻燃性能具有十分重要的意义。
发明内容
本发明的一个目的是提供一种抗紫外阻燃型环氧树脂固化剂,所述固化剂含有的紫外吸收活性基团和阻燃活性基团参与环氧树脂的固化反应,均匀地将紫外吸收元素和阻燃元素引入环氧树脂链中,大大地提高了环氧树脂的使用性能。
本发明的另一个目的是提供上述抗紫外阻燃型环氧树脂固化剂的制备方法。
为实现上述发明目的,本发明提供以下技术方案:
一方面,本发明提供一种抗紫外阻燃型环氧树脂固化剂,结构如式(I)所示:
第二方面,本发明提供式(I)化合物的制备方法,包括以下步骤:
步骤(1):对硝基苯甲醛与乙酸酐反应制得对硝基肉桂酸;
步骤(2):对硝基肉桂酸酰化制得对硝基肉桂酰氯;
步骤(3):对硝基肉桂酰氯与2,4-二羟基二苯甲酮反应制得式(a)化合物,即2-羟基-4-(2-对硝基苯基丙烯酸酯基)二苯甲酮;
步骤(4):式(a)化合物还原得到式(b)化合物,即2-羟基-4-(2-对氨基苯基丙烯酸酯基)二苯甲酮;
步骤(5):式(b)化合物与DOPO反应得到式(I)化合物;反应方程式如下:
本发明所述的抗紫外阻燃型环氧树脂固化剂制备方法,所述步骤(5)中式(b) 化合物与DOPO是在惰性气体保护下反应得到,所用惰性气体为氮气、氩气或氦气中的一种。
本发明所述的抗紫外阻燃型环氧树脂固化剂制备方法,所述步骤(5)中所得式(I)化合物在甲醇-丙酮混合溶剂中重结晶纯化,所述甲醇-丙酮混合溶剂的体积比为3:1。
本发明提供的抗紫外阻燃型环氧树脂固化剂,在固化环氧树脂材料的反应过程中,能够均匀地在固化后的树脂材料中通过化学键均匀、牢固地引入紫外吸收活性基团邻羟基二苯甲酮和阻燃活性基团DOPO,同时赋予环氧树脂固化后的材料优良的抗紫外性能和阻燃性能。
附图说明
图1是本发明固化剂制得环氧树脂膜在紫外照射下的拉伸强度值;
图2是本发明固化剂制得环氧树脂膜在紫外照射下的黄变值变化情况。
具体实施方式
实施例1对硝基肉桂酸的制备
称取15g对硝基苯甲醛、6g乙酸钠于反应瓶中,加入乙酸酐30mL,180℃回流反应8h,反应结束后,加水50mL,饱和碳酸钾溶解调pH至8,活性炭脱色,趁热过滤,盐酸调节pH至4左右,过滤,即得。
ES:M/Z 181[M+H]+。
实施例2:对硝基肉桂酰氯的制备
称取5g实施1所得物对硝基肉桂酸于反应瓶中,加入二氯亚砜30mL,DMF 2mL,升温回流2h,减压蒸除溶剂,直接用于下一步。
实施例3:2-羟基-4-(2-对硝基苯基丙烯酸酯基)二苯甲酮的制备
称取2,4-二羟基二苯甲酮3.4g于反应瓶中,加入三乙胺3mL,四氢呋喃20mL, 0-5℃下缓慢滴加10mL溶解有实施例2所得物的四氢呋喃溶液,滴毕,0-10℃下继续搅拌4h,反应结束后,加入水30mL,二氯甲烷萃取(3*50mL),无水硫酸钠干燥,柱层析纯化即得标题化合物。
ES:M/Z 390[M+H]+。
1H NMR(600MHz,CDCl3)(δ,ppm):8.51~8.50(m,2H),8.02~8.00(m,2H), 7.82~7.81(m,2H),7.55~7.53(m,2H),7.40~7.39(m,2H),6.98~6.95(m,2H), 6.50(s,1H),6.37(s,1H),5.00(s,1H).
实施例4:2-羟基-4-(2-对氨基苯基丙烯酸酯基)二苯甲酮的制备
称取1g实施例3化合物2-羟基-4-(2-对硝基苯基丙烯酸酯基)二苯甲酮于反应瓶中,加入30ml甲醇溶解,溶解有0.6g硫氢化钠的甲醇溶液10ml,回流反应10h,反应结束,减压旋除甲醇,加入冷水30ml,过滤,所得固体柱层析混合的标题化合物。
ES:M/Z 360[M+H]+。
1H NMR(600MHz,CDCl3)(δ,ppm):8.03~8.01(m,2H),7.82~7.81(m,2H), 7.54~7.53(m,2H),7.19~7.17(m,2H),6.42~6.39(m,3H),6.19(s,1H),6.10(s, 1H),5.00(s,1H).
实施例5:式(I)化合物的制备
称取10gDOPO于反应瓶中,加入8.6g实施例4所得物2-羟基-4-(2-对氨基苯基丙烯酸酯基)二苯甲酮,150ml二氧六环,氮气保护下回流反应10h,反应结束后,冷却至室温,减压蒸除溶剂,甲醇/丙酮(体积比3:1)重结晶即得标题化合物。
ES:M/Z 360[M+H]+。
1H NMR(600MHz,CDCl3)(δ,ppm):8.11(m,1H),8.02~7.98(m,3H),7.82~7.78 (m,4H),7.56~7.54(m,2H),7.51(m,1H),7.39~7.37(m,1H),7.13~7.14(m,4H), 7.06~7.04(m,2H),6.58~6.56(m,2H),6.32(s,2H),5.05(s,1H),4.01~3.99(m,1H), 3.21~3.19(m,1H),3.03~3.02(m,1H).
实验例1阻燃性能测试
将双酚A型环氧树脂、表1中的固化剂混合后,在100-110℃下搅拌均匀后将所得组合物浇注到模具中,按80℃/2小时预固化,160℃/5小时固化,200℃ /4小时固化工艺成型,得到环氧树脂膜,依据UL94《设备和器具部件材料的可燃性能试验》中的垂直燃烧试验方法测定阻燃性能,结果见表1。
表1
实验例2抗紫外性能测定
将双酚A型环氧树脂100g、实施例5化合物28g混合后,在100-110℃下搅拌均匀后将所得组合物浇注到模具中,按80℃/2小时预固化,160℃/5小时固化,200℃/4小时固化工艺成型,得到环氧树脂膜,作为实验组;将双酚A型环氧树脂100g、桐油酸酐8g、环氧树脂促进剂EP-184混合后,同法制得环氧树脂膜,作为对照组。在紫外波长为340nm,强度为0.76W/m2,在60℃下辐照暴露 3个月,其拉伸强度变化见图1,黄变值变化见图2。
由图1和图2克制可知,,本发明固化剂制备的环氧树脂膜具有优良的抗紫外吸收性能。
Claims (4)
3.如权利要求2所述的制备方法,所述步骤(5)中式(b)化合物与DOPO是在惰性气体保护下反应得到,所用惰性气体为氮气、氩气或氦气中的一种。
4.如权利要求2所述的制备方法,所述步骤(5)中所得式(I)化合物在甲醇-丙酮混合溶剂中重结晶纯化,所述甲醇-丙酮混合溶剂的体积比为3:1。
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