Bis-substituted thiophene-containing oxime sulfonates photoacid generators for cationic polymerization under UV-visible LED irradiation

被引:22
作者
Sun, Xin [1 ]
Jin, Ming [1 ]
Wu, Xingyu [1 ]
Pan, Haiyan [1 ]
Wan, Decheng [1 ]
Pu, Hongting [1 ]
机构
[1] Tongji Univ, Sch Mat Sci & Engn, Dept Polymer Mat, 4800 Caoan Rd, Shanghaiz 201804, Peoples R China
基金
中国国家自然科学基金;
关键词
cationic photopolymerization; light-emitting diodes; oxime sulfonate; photoacid generators; photoinitiators; VERSATILE PHOTOINITIATORS; LIGHT; SYSTEMS; DYES; PHOTOPOLYMERIZATION; PHOTOCHEMISTRY; ABSORPTION; DESIGN; SALTS; NM;
D O I
10.1002/pola.28951
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
Three novel types of thiophene-containing oxime sulfonates with a big -conjugated system were reported as non-ionic photoacid generators. The irradiation of the newly synthesized photoacid generators using near UV-visible light-emitting diodes (LEDs) (365-475 nm) results in the cleavage of two weak NO bonds in single molecules, which lead to the generation of different sulfonic acids in good quantum and chemical yields. The mechanism for the NO bond cleavage for acid generation was supported by the UV-visible spectra and real-time H-1 NMR spectra. They are developed as high-performance photoinitiators without any additives for the cationic polymerization of epoxide and vinyl ether upon exposure to near-UV and visible LEDs (365-475 nm) at low concentration. In the field of photopolymerization, especially visible light polymerization, it has great potential for application. (c) 2018 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2018, 56, 776-782
引用
收藏
页码:776 / 782
页数:7
相关论文
共 35 条
[1]  
[Anonymous], 2 PHOTON PHOTOPOLYME
[2]  
[Anonymous], 2013, UV LED PRESENTED RAD
[3]  
[Anonymous], 1995, EUR COAT J
[4]   Curcumin: A naturally occurring long-wavelength photosensitizer for diaryliodonium salts [J].
Crivello, JV ;
Bulut, U .
JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2005, 43 (21) :5217-5231
[5]   Photopolymerization upon LEDs: new photoinitiating systems and strategies [J].
Dietlin, Celine ;
Schweizer, Stephane ;
Xiao, Pu ;
Zhang, Jing ;
Morlet-Savary, Fabrice ;
Graff, Bernadette ;
Fouassier, Jean-Pierre ;
Lalevee, Jacques .
POLYMER CHEMISTRY, 2015, 6 (21) :3895-3912
[6]   Near UV-vis LED-excitable two-branched sensitizers for cationic, radical, and thiol-ene photopolymerizations [J].
Fang, Bingqing ;
Jin, Ming ;
Wu, Xingyu ;
Zhang, Yuan ;
Wan, Decheng .
DYES AND PIGMENTS, 2016, 126 :54-61
[7]   Wavelength-Dependent Photochemistry of Oxime Ester Photoinitiators [J].
Fast, David E. ;
Lauer, Andrea ;
Menzel, Jan P. ;
Kelterer, Anne-Marie ;
Gescheidt, Georg ;
Barner-Kowollik, Christopher .
MACROMOLECULES, 2017, 50 (05) :1815-1823
[8]   Design of D-π-A type photoacid generators for high efficiency excitation at 405 nm and 800 nm [J].
Jin, Ming ;
Xu, Haoran ;
Hong, Hong ;
Malval, Jean-Pierre ;
Zhang, Yuan ;
Ren, Aimin ;
Wan, Decheng ;
Pu, Hongting .
CHEMICAL COMMUNICATIONS, 2013, 49 (76) :8480-8482
[9]   Two-photon absorption and polymerization ability of intramolecular energy transfer based photoinitiating systems [J].
Jin, Ming ;
Malval, Jean-Pierre ;
Versace, Davy-Louis ;
Morlet-Savary, Fabrice ;
Chaumeil, Helene ;
Defoin, Albert ;
Allonas, Xavier ;
Fouassier, Jean-Pierre .
CHEMICAL COMMUNICATIONS, 2008, (48) :6540-6542
[10]   Two-photon microstructure-polymerization initiated by a coumarin derivative/iodonium salt system [J].
Li, CD ;
Luo, L ;
Wang, SF ;
Huang, WT ;
Gong, QH ;
Yang, YY ;
Feng, SJ .
CHEMICAL PHYSICS LETTERS, 2001, 340 (5-6) :444-448