桐油基光引发剂的制备及性能
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摘要
以桐油(TO)、桐酸(TA)和马来酸酐(MA)为原料,经Diels-Alder反应,得到桐油酸酐(TOM1～3)及桐酸酸酐(TAM)。在三乙胺催化下,TOM、TAM分子中酸酐分别与Irgacure2959[2-羟基-4-(2-羟乙氧基)-2-甲基苯丙酮]的羟基反应,合成了4种裂解型光引发剂(TOMG1～3,TAMG)。用FTIR、1HNMR及HRMS表征了其结构,利用UV-vis考察了引发剂的光分解过程,用实时红外光谱探究了引发剂引发1,6-己二醇二丙烯酸酯(HDDA)的聚合过程。结果表明,在Irgacure2959和桐油改性的几种光引发剂中,TOMG3光引发性能最优。在紫外光强度为28 mW/cm2的光照下,以HDDA、PUA(聚氨酯丙烯酸酯)及TOMG3按质量比46:46:8复配的胶液的光固化表干时间为60 s,凝胶率为96%,固化膜的硬度及柔韧性分别为6H和5 mm,对玻璃的附着力为0级。
Tung oil anhydrides(TOM1～TOM3) and tung acid anhydride(TAM) were synthesized from tung oil(TO) and tung acid(TA) with maleic anhydride(MA) via the Diels-Alder reaction.Then,the obtained compounds reacted with the hydroxyl groups of 2-hydroxy-4-(2-hydroxyethoxy)-2-methylpropiophenone(Irgacure2959) to produce four cleavage photoinitiators(TOMG1～TOMG3,TAMG) in the presence of catalytic amount of triethylamine.Theses initiators were characterized by FTIR,1 HNMR and HRMS spectroscopy.Their decomposition processes were investigated by UV visible spectroscopy.The photopolymerization dynamics of 1,6-hexanediol diacrylate(HDDA) initiated photoinitiators were studied using real-time FTIR technology.The results showed that initator TOMG3 had the best photoinitiation performance among Irgacure 2959 and the tung oil modified photoinitiators.The mixture of HDDA,PUA(polyurethane acrylate) and TOMG3 in a mass ratio of 46 :46 :8 could be cured within 60 s under ultraviolet light irradiation with an intensity of 28 m W/cm2,and the gelation rate reached 96%.The hardness,flexibility and adhesion to glass of the cured film was 6 H,5 mm,grade 0,respectively.
Tung oil anhydrides(TOM1～TOM3) and tung acid anhydride(TAM) were synthesized from tung oil(TO) and tung acid(TA) with maleic anhydride(MA) via the Diels-Alder reaction.Then,the obtained compounds reacted with the hydroxyl groups of 2-hydroxy-4-(2-hydroxyethoxy)-2-methylpropiophenone(Irgacure2959) to produce four cleavage photoinitiators(TOMG1～TOMG3,TAMG) in the presence of catalytic amount of triethylamine.Theses initiators were characterized by FTIR,1 HNMR and HRMS spectroscopy.Their decomposition processes were investigated by UV visible spectroscopy.The photopolymerization dynamics of 1,6-hexanediol diacrylate(HDDA) initiated photoinitiators were studied using real-time FTIR technology.The results showed that initator TOMG3 had the best photoinitiation performance among Irgacure 2959 and the tung oil modified photoinitiators.The mixture of HDDA,PUA(polyurethane acrylate) and TOMG3 in a mass ratio of 46 :46 :8 could be cured within 60 s under ultraviolet light irradiation with an intensity of 28 m W/cm2,and the gelation rate reached 96%.The hardness,flexibility and adhesion to glass of the cured film was 6 H,5 mm,grade 0,respectively.
引文
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[2]Noreen A,Zia K M,Zuber M,et al.Bio-based polyurethane:An efficient and environment friendly coating systems:A review[J].Progress in Organic Coatings,2016,91:25-32.
[3]Zia K M,Noreen A,Zuber M,et al.Recent developments and future prospects on bio-based polyesters derived from renewable resources:A review[J].International Journal of Biological Macromolecules,2016,82:1028-1040.
[4]Zhang L L,Luo M C,Eviatar N,et al.Development of microsatellite markers in tung tree(verniciafordii)using cassava genomic sequences[J].Plant Molecular Biology Reporter,2015,33(4):893-904.
[5]Cintia M,Mirta A I,Mirna M A,et al.Polymeric networks based on tung oil:Reaction and modification with green oil monomers[J].European Polymer Journal,2015,67:551-560.
[6]Trumbo D L,Mote B E.Synthesis of tung oil-diacrylate copolymers via the Diels-Alder reaction and properties of films from the copolymers[J].Applied Polymer Science,2001,80(12):2369-2375.
[7]Huang K,Zhang P,Zhang J W,et al.Preparation of biobased epoxies using tung oil fatty acid-derived C21 diacid and C22 triacid and study of epoxy properties[J].Green Polymer Chemistry,2013,15(9):2466-2475.
[8]Huang K,Liu Z S,Zhang J W,et al.Epoxy monomers derived from tung oil fatty acids and its regulable thermosets cured in two synergistic ways[J].Biomacromolecules,2014,15(3):837-843.
[9]Shibata M,Teramoto N,Yoshihara,et al.Preparation and properties of biocomposites composed of sorbitol-based epoxy resin,tung oil-pyrogallol resin,and wood flour[J].Journal of Applied Polymer Science,2012,DOI:10.1002/APP.38739.
[10]Thanamongkollit N,Miller K R,Soucek M D.Synthesis of UV-curable tung oil and UV-curable tung oil based alyyd[J].Progress in Organic Coatings,2012,73(4):425-434.
[11]Guo R,Gao Y,Wu M,et al.Aliphatic ketones and aldehydes as water-soluble photo initiators for the photopolymerization of methacrylic acid[J].Polymer,2013,54(18):4940-4947.
[12]Wei Jun(韦军),Zheng Xiaojuan(郑小娟),Jiang Yifeng(蒋乙峰).Preparation and properties of polyurethane-type polymeric benzophenone photoinitiators[J].Polymer Materials Science and Engineering(高分子材料科学与工程),2015,31(4):42-46.
[13]Dell'Erba I E,Arenas G F,Schroeder W,et al.Hybrid organicinorganic macromolecular photoinitiator system for visible-light photopolymerization[J].Progress in Organic Coatings,2014,77(11):1848-1853.
[14]Liang S,Yang Y D,Zhou H Y,et al.Novel polymerizable HMPP-type photoinitiator with carbamate:Synthesis and photoinitiating behaviors[J].Progress in Organic Coatings,2017,110:128-133.
[15]Zhang Y,He Y,Nie J,et al.α-hydroxyalkyl ketones derivatives used as photoinitiators for photografting field[J].Journal of Photochemistry&Photobiology A Chemistry,2017,349:193-196.
[16]Valandro S R,Poli A,Venancio T,et al.A novel biopolymeric photoinitiator based on chitosan and thioxanthone derivative:Synthesis,characterization and efficiency in photopolymerization[J].Journal of Photochemistry and Photobiology A:Chemistry,2016,327:15-20.
[17]Zhang Haizhao(张海召).Preparation of functional tung oil derivatives and application in UV curing coating[D].Tianjin:Hebei University of Technology(河北工业大学),2017.
[18]Han W S,Lin B P,Yang H,et al.Synthesis and properties of UV-curable hyperbranced polyurethane acrylate oligomers containing carboxyl groups[J].Polymer Bulletin,2012,68(4):1009-1022.
[19]Huang J J,Yuan T,Ye X Y,et al.Study on the UV curing behavior of tung oil:Mechanism,curing activity and film-forming property[J].Industrial Crops&Products,2018,112:61-69.
[20]Zhang Haizhao(张海召),Zhou Hongyong(周宏勇),Wang Jiaxi(王家喜).Synthesis,characterization and UV curable property of acrylate modified tung oil-based emulsifier[J].Chemical Industry and Engineering Progress(化工进展),2017,36(10):3860-3865.
[21]Tan Xianglu(谭湘璐),Deng Jianru(邓剑如),Luo Sai(罗赛),et al.Preparation and properties of tung oil-based waterborne UV-curable resin[J].Fine Chemicals(精细化工),2016,33(8):862-866.
[22]Huang Y G,Ye G D,Yang J W.Synthesis and properties of UV-curable acrylate functionalized tung oil based resins via Diels-Alder reaction[J].Progress in Organic Coatings,2015,78:28-34.