Developing thioxanthone based visible photoinitiators for radical polymerization

被引：47

作者：

Wu, Qingqing ^{[1
]}

Xiong, Ying ^{[1
]}

Liang, Qiuhong ^{[1
]}

Tang, Hongding ^{[1
]}

机构：

[1] Wuhan Univ, Coll Chem & Mol Sci, Wuhan 430072, Peoples R China

来源：

RSC ADVANCES | 2014年 / 4卷 / 94期

基金：

美国国家科学基金会;

关键词：

ACID-DERIVATIVES; PHOTOPOLYMERIZATION; BENZOPHENONE; FLUORESCENCE; REACTIVITY; ANTHRACENE; COATINGS;

D O I：

10.1039/c4ra07614a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Three new amino-thioxanthone photoinitiators (PIs) with different substituents on nitrogen, including 2-allyl(methyl)amino-9H-thioxanthen-9-one (PI-1), 2-benzyl(methyl)amino-9H-thioxanthen-9-one (PI-2) and 2-butyl(methyl)amino-9H-thioxanthen-9-one (PI-3) were synthesized and characterized. They showed high molar extinction coefficients and very broad absorption range in the visible region. Among them, PI-2 showed the best visible light photoinitiating properties evidenced by the fact that it successfully initiated polymerization of 1,6-hexanedioldiacrylate (HDDA) under xenon light exposure (28 mW cm(-2)) both in the presence and absence of N,N-dimethylaniline (DMA) for 0.5 h with 92% and 52% conversion, respectively. For TMPTA, the conversion of PI-2 and PI-2/N-methyldiethanolamine (MDEA) systems is 32% and 62% under xenon lamp exposure for 10 min. The photoinitiation mechanisms were analysed through EPR, fluorescence spectra and visible light photolysis experiments.

引用

页码：52324 / 52331

页数：8

共 53 条

[11] PHOTOSENSITISED OXIDATION OF AMINES .1. USE OF BENZOPHENONE AS A SENSITISER [J].

BARTHOLOMEW, RF ;

DAVIDSON, RS .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1971, (12) :2342-+

[12] Novel water soluble copolymers based on thioxanthone: photochemistry and photoinitiation activity [J].

Corrales, T ;

Catalina, F ;

Allen, NS ;

Peinado, C .

JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 2005, 169 (01) :95-100

[13] Photochemical study and photoinitiation activity of macroinitiators based on thioxanthone [J].

Corrales, T ;

Catalina, F ;

Peinado, C ;

Allen, NS ;

Rufs, AM ;

Bueno, C ;

Encinas, MV .

POLYMER, 2002, 43 (17) :4591-4597

[14]

Davidson R. S., 1972, J CHEM SOC PERK T, V2, P2351

[15] Thioxanthone based 9[2-(methyl-phenyl-amino)-acetyl]-thia-naphthacene-12-one as a visible photoinitiator [J].

Dogruyol, Sevnur Keskin ;

Dogruyol, Zekeriya ;

Arsu, Nergis .

JOURNAL OF LUMINESCENCE, 2013, 138 :98-104

[16] A Thioxanthone-Based Visible Photoinitiator [J].

Dogruyol, Sevnur Keskin ;

Dogruyol, Zekeriya ;

Arsu, Nergis .

JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2011, 49 (18) :4037-4043

[17]

Drobny J.G., 2010, Radiation technology for polymers

[18] The influence of the photophysics of 2-substituted thioxanthones on their activity as photoinitiators [J].

Encinas, MV ;

Rufs, AM ;

Corrales, T ;

Catalina, F ;

Peinado, C ;

Schmith, K ;

Neumann, MG ;

Allen, NS .

POLYMER, 2002, 43 (14) :3909-3913

[19] The persistent radical effect: A principle for selective radical reactions and living radical polymerizations [J].

Fischer, H .

CHEMICAL REVIEWS, 2001, 101 (12) :3581-3610

[20]

Fouassier J.P., 2012, Photoinitiators for Polymer Synthesis: Scope, Reactivity, and Efficiency

← 1 2 3 4 5 6 →