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。
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(intermediateⅠ)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](intermediateⅡ).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 intermediateⅡ,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.
作者
赵雪钦
王博威
许文胜
沈华伟
陈立功
李阳
ZHAO Xueqin;WANG Bowei;XU Wensheng;SHEN Huawei;CHEN Ligong;LI Yang(School of Chemical Engineering and Technology,Tianjin University,Tianjin 300350,China;Zhejiang Institute of Tianjin University,Zhejiang 312300,Shaoxing,China;Tianjin Engineering Research Center of Functional Fine Chemicals,Tianjin 300350,China;Shaoxing Xingxin New Materials Co.,Ltd.,Shaoxing 312369,Zhejiang,China)
出处
《精细化工》
EI
CAS
CSCD
北大核心
2024年第4期772-777,871,共7页
Fine Chemicals
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
hindered amine light stabilizers
cyanuric chloride
hydrolysis
automotive varnishes
hydroxyl
functional materials
