用于水性车漆的受阻胺光稳定剂的合成及性能
Synthesis and properties of a hindered amine light stabilizer used in automotive varnish
赵雪钦 1王博威 2许文胜 1沈华伟 3陈立功 2李阳2
作者信息
- 1. 天津大学 化工学院,天津 300350
- 2. 天津大学 化工学院,天津 300350;天津大学浙江研究院,浙江 绍兴 312300;天津功能精细化学品技术工程中心,天津 300350
- 3. 绍兴兴欣新材料股份有限公司,浙江 绍兴 312369
- 折叠
摘要
设计、合成了一种受阻胺光稳定剂(HALS)TM-3.首先,三聚氯氰和 N-丁基-2,2,6,6-四甲基-4-哌啶胺通过亲核取代反应合成了N-丁基-4,6-二氯-N-(2,2,6,6-四甲基-4-哌啶基)-1,3,5-三嗪-2-胺(中间体Ⅰ);中间体Ⅰ再与 N,N-双(2,2,6,6-四甲基-4-哌啶基)-1,6-己二胺反应生成了 N2,N2'-(己烷-1,6-二基)双[N4-丁基-6-氯-N2,N4-双(2,2,6,6-四甲基哌啶-4-基)-1,3,5-三嗪-2,4-二胺](中间体Ⅱ);最后,中间体Ⅱ水解生成目标化合物6,6'-{己烷-1,6-二基双[(2,2,6,6-四甲基哌啶-4-基)氮二基]}双{4-[丁基(2,2,6,6-四甲基哌啶-4-基)氨基]-1,3,5-三嗪-2-醇}(TM-3).采用 1HNMR、13CNMR、HRMS表征了TM-3的结构,通过UV-Vis、TGA考察了其性能,比较了TM-3和双(2,2,6,6-四甲基-4-哌啶基)癸二酸酯(HALS770)在汽车清漆涂料中的光稳定性.结果表明,TM-3 在 210 nm处具有强烈的UV-Vis吸收;热稳定性能良好,在400℃以前能保持热稳定,可以耐受较高的温度;TM-3在含水的有机溶剂中比HALS770具有更好的溶解性.加入TM-3的样品(样品 4)在模拟紫外光照射 800 h后色差为 6.01,光泽损失率为 4.6%;而加入HALS770 的样品(样品 5)色差达到 6.72,光泽损失率为 6.7%,说明TM-3 的光稳定优于HALS770.
Abstract
A hindered amine light stabilizer(HALS)TM-3 was designed and synthesized.N-butyl-4,6-dichloro-N-(2,2,6,6-tetramethyl-4-piperidinyl)-1,3,5-triazine-2-amine(intermediate Ⅰ)was firstly synthesized from nucleophilic substitution reaction of cyanuric chloride and N-butylamino-2,2,6,6-tetramethylpiperidinyl,which was then reacted with N,N-bis(2,2,6,6-tetramethylpiperidin-4-yl)-hexane-1,6-diamine to produce N2,N2'-(hexane-1,6-diyl)bis[N4-butyl-6-chloro-N2,N4-bis(2,2,6,6-tetramethylpiperidin-4-yl)-1,3,5-triazine-2,4-diamine](intermediate Ⅱ).Finally,target compound 6,6'-{hexane-1,6-diylbis[(2,2,6,6-tetramethylpiperidin-4-yl)azanediyl]}bis{4-[butyl(2,2,6,6-tetramethylpiperidin-4-yl)amino]-1,3,5-triazin-2-ol}(TM-3)was obtained by hydrolyzation of intermediate Ⅱ,and characterized by 1HNMR,13CNMR,HRMS,UV-Vis absorption spectra and TGA for structure and property analyses.The light stability of TM-3 and bis(2,2,6,6-tetramethyl-4-piperidyl)sebacate(HALS770)in automotive varnish coatings was further evaluated.The results showed that TM-3 displayed strong UV-Vis absorption at 210 nm and good thermal stability by maintaining thermal stability below 400℃and withstanding higher temperatures.TM-3 exhibited better solubility in aqueous organic solvents compared with HALS770.After 800 h of simulated ultraviolet irradiation,sample 4 with TM-3 added showed a chromatic aberration of 6.01 and a gloss loss rate of 4.6%,while sample 5 with HALS770 added displayed a chromatic aberration of 6.72 and a gloss loss rate of 6.7%,indicating that TM-3 had better light stability than HALS770.
关键词
受阻胺光稳定剂/三聚氯氰/水解/汽车清漆/羟基/功能材料Key words
hindered amine light stabilizers/cyanuric chloride/hydrolysis/automotive varnishes/hydroxyl/functional materials引用本文复制引用
出版年
2024
NETL
NSTL
万方数据