CN111851065B - 一种紫外线吸收剂、合成方法及其应用 - Google Patents
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Abstract
本发明涉及一种紫外线吸收剂、合成方法及应用，合成方法为：首先将乙醇胺和BPTCD加入到有机溶剂中，升温合成BTDA‑ETA；接着将BTDA‑ETA和三聚氯氰在0℃的有机溶剂中反应合成TCT‑BTDA‑ETA；然后将TCT‑BTDA‑ETA和HEDP在有机溶剂中混合均匀，升温至45‑55℃，合成紫外线吸收剂。本发明的紫外线吸收剂合成工艺简单、成本低，该紫外线吸收剂不仅具有优良的抗紫外性能，还具有阻燃性能，适合用于棉织物的整理，与其他单一性能的整理剂相比，具有更好的实用性，可同时解决两方面的问题，具有良好的经济效益。
Description
技术领域
本发明涉及一种紫外线吸收剂、合成方法及其应用，属于紫外线吸收剂技术领域。
背景技术
紫外线是波长在180～400nm的电磁波。适量的紫外辐射具有杀菌作用，并能促进维生素D的合成，有利于人体健康，但过量的紫外线对人体十分有害。现代科学研究表明，紫外线对人体的有害影响要远大于它的有利作用，过量的紫外线辐射会诱发皮肤病，甚至皮肤癌，亦会引起白内障并降低人体的免疫功能。因此，紫外线的防护越来越为人们所关注。
紫外线吸收剂是一类能够强烈地选择性吸收高能量紫外光并进行能量转换，以热能或无害的低辐射形式将能量释放或消耗的物质，广泛应用于高分子材料、纺织品加工及其他领域。目前常用的紫外线吸收剂主要有二苯甲酮类、苯并三唑类、水杨酸酯类、取代丙烯腈类等等。但每类紫外线吸收剂都有不足之处，例如：二苯甲酮类的抗紫外效果虽然良好，但由于成本较贵限制了其发展应用，而且易使制品显黄色，同时与高分子聚合物相容性较差，用途较小；苯并三唑类能够较强地吸收300～400nm波长范围的紫外光线，但对400nm以上的可见光部分几乎无吸收；水杨酸脂类虽然价格低廉，但吸收波长范围比较窄，而且对紫外线的吸收能力较弱。
另一方面，棉织物因具有良好的透气性和舒适性，广泛用于服装面料。但是，由于棉纤维的主要成分是纤维素，是由葡萄糖为基本结构单元重复而成的，结构较为简单，因此具有易燃性，在使用方面具有巨大的安全隐患。据全世界数据统计显示，因纺织品导致的燃烧或燃烧加剧的案例所占比例达到50％以上。因此，研究出高效耐久的棉用阻燃剂对人类的发展以及生活具有十分重要的意义。
发明内容
本发明的目的在于解决现有技术的不足，提供一种紫外线吸收剂，其具有优良的抗紫外性能，并且兼具优良的阻燃性。
本发明的另一目的在于提供上述紫外线吸收剂的合成方法。
技术方案
一种紫外线吸收剂，其分子结构式如下所示：
上述紫外线吸收剂的合成方法，包括如下步骤：
(1)制备BTDA-ETA(3,3'4',4-二苯甲酮四羧酸二酐-乙醇胺):
将乙醇胺和BPTCD(3,3'4',4-二苯甲酮四羧酸二酐)加入到有机溶剂中，在氮气氛围下，升温至115-125℃，搅拌反应10-15h，冷却后加入去离子水将溶于有机溶剂的反应产物析出沉淀出来，然后分别用去离子水和乙醚清洗干净，将得到的固体干燥，即为BTDA-ETA；
(2)制备TCT-BTDA-ETA(三聚氯氰-3,3'4',4-二苯甲酮四羧酸二酐-乙醇胺)：
将BTDA-ETA和三聚氯氰在0℃的有机溶剂中混合均匀，然后加入缚酸剂，调节反应过程中的pH为6-7，搅拌反应3-6h后，过滤除去反应液中的固体，然后往反应液中加入去离子水，混合均匀后得到沉淀，分别使用去离子水和乙醚离心清洗沉淀，然后烘干，得到TCT-BTDA-ETA；
(3)HEDP-TCT-BTDA-ETA(羟基乙叉二膦酸-三聚氯氰-3,3'4',4-二苯甲酮四羧酸二酐-乙醇胺)的合成：
将TCT-BTDA-ETA和HEDP(羟基乙叉二膦酸)在有机溶剂中混合均匀，升温至45-55℃并加入无水碳酸钠调pH为6-7，搅拌反应3-6h后，过滤除去反应液中的固体，然后往反应液中加入去离子水，混合均匀后得到沉淀，用去离子水离心清洗干净后，烘干，得到HEDP-TCT-BTDA-ETA，即为紫外线吸收剂。
进一步，步骤(1)中，乙醇胺和3,3'4',4-二苯甲酮四羧酸二酐的摩尔比为2:1，乙醇胺可稍微过量以确保反应可充分进行。
进一步，步骤(1)-(3)中，所述有机溶剂为二甲基甲酰胺(DMF)。
进一步，步骤(2)中，BTDA-ETA和三聚氯氰的摩尔比为1:2，三聚氯氰可稍微过量。
进一步，步骤(2)中，所述缚酸剂为碳酸钾。
进一步，步骤(3)中，所述TCT-BTDA-ETA和羟基乙叉二膦酸的摩尔比为1:2，HEDP可稍微过量。
本发明的合成路线如下：
上述紫外线吸收剂用于整理棉织物的应用，应用方法为：将紫外线吸收剂用水配制成浓度为60g/L的溶液作为整理剂，加入碳酸钠和棉织物，搅拌均匀，浴比为1:30，碳酸钠浓度为15g/L，然后升温至90℃，恒温震荡1-4h后，取出织物，水洗并55-65℃烘干，接着再以130℃焙烘5min。
本发明同现有技术相比，具有以下有益效果：
(1)本发明使该整理剂同时具有阻燃和抗紫外两种作用，与其他单一性能的整理剂相比，具有更好的实用性，在生产方面可以同时解决两方面的问题。
(2)具有更好的经济效益，不仅在生产过程中可以减少一个环节减少生产时间和耗能，而且成本总和也低于两种分开工艺的成本之和。
附图说明
图1为实施例1制得的紫外线吸收剂的红外图谱；
图2为实施例1制得的紫外线吸收剂的1H NMR图谱。
具体实施方式
下面结合附图和具体实施例对本发明作进一步说明。
实施例1
一种紫外线吸收剂，分子结构式如下：
上述紫外线吸收剂的合成方法，包括如下步骤：
(1)制备BTDA-ETA(3,3'4',4-二苯甲酮四羧酸二酐-乙醇胺):
将乙醇胺(1,12.216g,0.200mol)和BPTCD(2,32.223g,0.100mol)加入到150mlDMF中，在氮气氛围下，升温至120℃，搅拌反应12h，冷却后加入去离子水将反应产物沉淀出来，然后分别用去离子水和乙醚清洗干净，将得到的固体干燥，即为BTDA-ETA；
(2)制备TCT-BTDA-ETA(三聚氯氰-3,3'4',4-二苯甲酮四羧酸二酐-乙醇胺)：
将BTDA-ETA(1,20.525g,0.050mol)和三聚氯氰(2,18.44g,0.100mol)在150ml、0℃的DMF中混合均匀，然后加入缚酸剂碳酸钾，调节反应过程中的pH，搅拌反应4h后，过滤除去反应液中的固体，然后往反应液中加入去离子水，混合均匀后得到沉淀，分别使用去离子水和乙醚离心清洗沉淀，然后烘干，得到TCT-BTDA-ETA；
(3)HEDP-TCT-BTDA-ETA(羟基乙叉二膦酸-三聚氯氰-3,3'4',4-二苯甲酮四羧酸二酐-乙醇胺)的合成：
将TCT-BTDA-ETA(1,13.354g,0.050mol)和HEDP(2,20.60g,0.100mol)在150mlDMF中混合均匀，升温至50℃并加入无水碳酸钠调pH6-7，搅拌反应4h后，过滤除去反应液中的固体，然后往反应液中加入去离子水，混合均匀后得到沉淀，用去离子水离心清洗干净后，烘干，得到HEDP-TCT-BTDA-ETA，即为紫外线吸收剂。
采用傅立叶变换红外光谱(FTIR)仪器测定实施例1制得的紫外线吸收剂，其光谱范围为4000～400cm-1。实施例1制得的紫外线吸收剂的红外图谱见图1，由图1可以看出，3063cm-1附近为P-OH键伸缩振动峰；2943cm-1附近为-CH3伸缩振动峰；2878cm-1附近为-CH2-伸缩振动峰；1777cm-1附近为酰胺基伸缩振动峰；1709cm-1为芳香酮伸缩振动峰；1653cm-1为三嗪环-C＝N伸缩振动峰；1478cm-1为苯环骨架伸缩振动峰，这与要合成的产物的化学结构特征一致。
采用核磁共振分析仪来分析实施例1制得的紫外线吸收剂的结构，测试选择氘代DMSO作为溶剂。实施例1制得的紫外线吸收剂的1H NMR图谱见图2，根据谱峰积分面积和化学位移进行H归属解析，1H NMR(400MHz,DMSO)δ8.22-8.20(m,2H),8.12-8.08(m,4H),4.37(t,J＝5.3Hz,4H),3.94(t,J＝5.3Hz,4H),3.19(s,6H).由于产物中的羟基氢是活泼性氢，以DMSO作为溶剂时，羟基氢有可能显示不出来。由数据可确定测出来的氢一共有20个，根据羟基峰的位置和数量和红外分析一起对比确定实施例1制得产物与要合成的目标产物一致。
应用测试：
将实施例1制得的紫外线吸收剂用于整理棉织物：将紫外线吸收剂用水配制成浓度为60g/L的溶液作为整理剂，加入碳酸钠和棉织物，搅拌均匀，浴比为1:30，碳酸钠浓度为15g/L，然后升温至90℃，恒温震荡2h后，取出织物，水洗并60℃烘干，接着再以130℃焙烘5min。
取30块洗净、烘干的棉织物(15cm×5.8cm)分三组，第一组作为空白样布，第二组和第三组按上述方法进行整理，得到整理后的棉织物。
1.将整理后的棉织物进行抗紫外性能测定
UPF是表示织物防护紫外线的能力，采用YG(B)912E型纺织品防紫外性能测试仪在280-400nm波长范围内测试与评价，测试标准为GB/T18830-2009，通过测出的UVA、UVB和UPF值，来判断产物是否具有抗紫外性能。
表1第一组空白样布的UPF值测定
在第二组整理后的棉织物中随机取4块布样，测试结果如表2所示：
表2整理后织物的UPF值测定
在第三组整理后的棉织物中随机取5块布样，测试结果如表3所示：
表3整理后织物的UPF值测定
按GB/T18830-2009测定，当样品的UPF>40，且T(UVA)AV<5％时，可称为“防紫外线产品”[4]，由数据可知，第001组和002组达到要求。
根据测试结果可得出：整理后的棉织物对UVA的屏蔽率达97.36％，对UVB的屏蔽率达98.60％，UPF值达69.70，整体性能优良，符合“防紫外线产品”标准。
2.将整理后的棉织物进行阻燃性能测定
根据ASTM D2863-2000标准，对棉织物进行极限氧指数测试，测得棉织物极限氧指数为27，达到阻燃标准。
Claims (9)
1.一种紫外线吸收剂，其分子结构式如下所示：
2.权利要求1所述紫外线吸收剂的合成方法，其特征在于，包括如下步骤：
(1)制备BTDA-ETA：
将乙醇胺和3,3'4',4-二苯甲酮四羧酸二酐加入到有机溶剂中，在氮气氛围下，升温至115-125℃，搅拌反应10-15h，冷却后加入去离子水将反应产物沉淀出来，然后分别用去离子水和乙醚清洗干净，将得到的固体干燥，即为BTDA-ETA；
(2)制备TCT-BTDA-ETA：
将BTDA-ETA和三聚氯氰在0℃的有机溶剂中混合均匀，然后加入缚酸剂，调节反应过程中的pH，搅拌反应3-6h后，过滤除去反应液中的固体，然后往反应液中加入去离子水，混合均匀后得到沉淀，分别使用去离子水和乙醚离心清洗沉淀，然后烘干，得到TCT-BTDA-ETA；
(3)HEDP-TCT-BTDA-ETA的合成：
将TCT-BTDA-ETA和羟基乙叉二膦酸在有机溶剂中混合均匀，升温至45-55℃并加入无水碳酸钠调pH6-7，搅拌反应3-6h后，过滤除去反应液中的固体，然后往反应液中加入去离子水，混合均匀后得到沉淀，用去离子水离心清洗干净后，烘干，得到HEDP-TCT-BTDA-ETA，即为紫外线吸收剂。
3.如权利要求2所述紫外线吸收剂的合成方法，其特征在于，步骤(1)中，乙醇胺和3,3'4',4-二苯甲酮四羧酸二酐的摩尔比为2:1。
4.如权利要求2所述紫外线吸收剂的合成方法，其特征在于，步骤(1)-(3)中，所述有机溶剂为二甲基甲酰胺。
5.如权利要求2所述紫外线吸收剂的合成方法，其特征在于，步骤(2)中，BTDA-ETA和三聚氯氰的摩尔比为1:2。
6.如权利要求2所述紫外线吸收剂的合成方法，其特征在于，步骤(2)中，所述缚酸剂为碳酸钾。
7.如权利要求2至6任一项所述紫外线吸收剂的合成方法，其特征在于，步骤(3)中，所述TCT-BTDA-ETA和羟基乙叉二膦酸的摩尔比为1:2。
8.权利要求1所述紫外线吸收剂用于整理棉织物的应用。
9.如权利要求8所述的应用，其特征在于，应用方法为：将紫外线吸收剂用水配制成浓度为60g/L的溶液作为整理剂，加入碳酸钠和棉织物，搅拌均匀，浴比为1:30，碳酸钠浓度为15g/L，然后升温至90℃，恒温震荡1-4h后，取出织物，水洗并55-65℃烘干，接着再以130℃焙烘5min。
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