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Journal of Polymer Research

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01-06-2020 | ORIGINAL MANUSCRIPT

Improvement on curing performance and morphology of E5I/TPGDA mixture in a free radical-cationic hybrid photopolymerization system

Authors: Ran Liu, Yuanyuan Xu, Jingwen Jia, Ping Chen, Fan Zhang, Lijun Zhang, Yu Chen

Published in: Journal of Polymer Research | Issue 6/2020

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Abstract

A visible light-induced free radical-cationic hybrid photopolymerization system co-initiated by diphenyliodonium hexafluorophosphate (IOPF) and diphenyl(2,4,6-trimethylbenzoyl)phosphine oxide (TPO). IOPF and TPO rapidly induced a mixture of diglycidyl ether of bisphenol-A epoxy resin (E51) and tripropylene glycol diacrylate (TPGDA) under a halogen lamp (λ = 380–580 nm). The curing rate of epoxy resin is significantly accelerated. The effect of weight ratio of IOPF/TPO, proportion of E51/TPGDA, benzoyl peroxide (BPO), 3,4-epoxycyclohexylmethyl-3′,4’epoxycyclohexyl carboxylate (ERL4221) on IOPF/TPO/TPGDA/E51 hybrid systems (HSs1–11) were studied by near infrared (NIR) spectroscopy. Free radical and cationic photopolymerization for TPO/TPGDA and IOPF/TPO/E51 were also investigated. TPO shows a sensitization effect to accelerate the curing of E51. Scanning electron microscopy (SEM) was used to observe the morphology of cured films, including surface and cross section. The film of hybrid system with BPO (HS-6) has the advantage of smooth surface and uniform cross section, while that of free radical system is obviously plicate. The acceleration of epoxy conversion is up to 85%, when ERL4221 was added.

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Chen Y, Li GL, Zhang H, Wang T (2011) Visible light curing of bisphenol-a epoxides and acrylates photoinitiated by (η⁶-benzophenone)(η⁵-cyclopentadienyl) iron hexafluorophosphate. J Polym Res 18:1425–1429

Gao N, Liu WQ, Ma SQ, Tang C, Yan ZL (2012) Cycloaliphatic epoxy resin modified by two kinds of oligo-fluorosiloxanes for potential application in light-emitting diode (LED) encapsulation. J Polym Res 19:9923

Mao Q, Bian L, Huang M (2011) Study of the visible light curing of vinyl ester resins using in situ Raman spectroscopy. J Polym Res 18:1751–1756

Kaewpirom S, Kunwong D (2012) Curing behavior and cured film performance of easy-to-clean UV-curable coatings based on hybrid urethane acrylate oligomers. J Polym Res 19:9995

Peters C, Ergeneman O, Sotiriou GA, Choi H, Nelson BJ, Hierold C (2015) Visible light curing of epon SU-8 based superparamagnetic polymer composites with random and ordered particle configurations. ACS Appl Mater Interfaces 7:193–200PubMed

Ortyl J, Topa M, Kamińska-Borek I, Popielarz R (2019) Mechanism of interaction of aminocoumarins with reaction medium during cationic photopolymerization of triethylene glycol divinyl ether. Eur Polym J 116:45–55

Shen W, Wang L, Cao Y, Zhang L, Chen H (2019) Cationic photopolymerization of liquid crystalline epoxide in mesogenic solvents and its application in polymer-stabilized liquid crystals. Polymer 172:231–238

Bazzano M, Marchisio D, Sangermano M, Wörner M, Pisano R (2019) A molecular dynamics approach to nanostructuring of particles produced via aerosol cationic photopolymerization. Chem Eng Sci 195:1021–1027

Zhao T, Yu R, Li X, Zhang Y, Yang X, Zhao X, Huang W (2019) A comparative study on 3D printed silicone-epoxy/acrylate hybrid polymers via pure photopolymerization and dual-curing mechanisms. J Mater Sci 54:5101–5111

10.

Vitale A, Cominotti M, Ameduri B, Bongiovanni R (2016) Semi-interpenetrating polymer networks by cationic photopolymerization: fluorinated vinyl ether chains in a hydrogenated vinyl ether network. Eur Polym J 82:122–131

11.

Noè C, Malburet S, Bouvet-Marchand A, Graillot A, Loubat C, Sangermano M (2019) Cationic photopolymerization of bio-renewable epoxidized monomers. Prog Org Coat 133:131–138

12.

You S, Wang P, Schimelman J, Hwang HH, Chen S (2019) High-fidelity 3D printing using flashing photopolymerization. Addit Manuf 30:100834

13.

Kamińska I, Ortyl J, Popielarz R (2016) Mechanism of interaction of coumarin-based fluorescent molecular probes with polymerizing medium during free radical polymerization of a monomer. Polym Test 55:310–317

14.

Ma X, Cao D, Fu H, You J, Gu R, Fan B, Nie J, Wang T (2019) Multicomponent photoinitiating systems containing arylamino oxime ester for visible light photopolymerization. Prog Org Coat 135:517–524

15.

Christmann J, Ley C, Allonas X, Ibrahim A, Croutxé-Barghorn C (2019) Experimental and theoretical investigations of free radical photopolymerization: inhibition and termination reactions. Polymer 160:254–264

16.

Crivello JV (2007) Hybrid free radical/cationic frontal photopolymerizations, J Polym Sci. Polym Chem 45:4331–4340

17.

Wang X, Xing W, Song L, Yu B, Shi Y, Yang W, Hu Y (2013) Flame retardancy and thermal properties of novel UV-curing epoxy acrylate coatings modified by phosphorus-containing hyperbranched macromonomer. J Polym Res 20:165

18.

Shao J, Huang Y, Fan Q (2014) Visible light initiating systems for photopolymerization: status, development and challenges. Polym Chem 5:4195–4210

19.

Qi Y, Li L, Fang Z, Zhong J, Dong Q (2014) Effects of small molecular weight silicon-containing acrylate on kinetics, morphologies, and properties of free-radical/cationic hybrid UV-cured coatings. J Appl Polym Sci 131:40655/1–40655/10

20.

Nowak D, Ortyl J, Kamińska-Borek I, Kukuła K, Topa M, Popielarz R (2017) Photopolymerization of hybrid monomers: part I: comparison of the performance of selected photoinitiators in cationic and free-radical polymerization of hybrid monomers. Polym Test 64:313–320

21.

Damian N, Joanna O, Iwona K-B, Katarzyna K, Monika T, Roman P (2018) Photopolymerization of hybrid monomers, part II: determination of relative quantum efficiency of selected photoinitiators in cationic and free-radical polymerization of hybrid monomers. Polym Test 67:144–150

22.

Ondrej S, Bohumil J, David V, Petr N (2016) Mechanical properties of polymer layers fabricated via hybrid free radical-cationic polymerization of acrylate, epoxide, and oxetane binders. Prog Org Coat 101:279–287

23.

Ge X, Ye Q, Song L, Misra A, Spencer P (2015) Visible-light initiated free-radical/cationic ring-opening hybrid photopolymerization of methacrylate/epoxy: polymerization kinetics, crosslinking structure, and dynamic mechanical properties. Macromo Chem Phys 216:856–872

24.

Crivello JV (2015) Hybrid acrylate-oxetane photopolymerizable systems, J Polym Sci. Polym Chem 53:594–601

25.

Schissel SM, Jessop JLP, Crivello JV, Liu S (2000) Photoinitiated cationic polymerization of epoxy alcohol monomers. J Polym Sci Polym Chem 38:389–401

26.

Shi S, Croutxé-Barghorna C, Allonas X (2017) Photoinitiating systems for cationic photopolymerization: ongoing push toward long wavelengths and low light intensities. Prog Polym Sci 65:1–41

27.

Chen Y, Jia X, Wang M, Wang T (2015) A synergistic effect of a ferrocenium salt on the diaryliodonium salt-induced visible-light curing of bisphenol-a epoxy resin. RSC Adv 5:33171–33176

28.

Schissel SM, Jessop JLP Enhancing epoxide kinetics and tuning polymer properties using hydroxylcontaining (meth)acrylates in hybrid photopolymerizations. Polymer 161:78–91

29.

Shi Y, Li G, Zhao B, Chen Y, Chao P, Zhang H, Wang X, Tao W Synthesis and optical properties of cationic cyclopentadienyl iron complexes with diphenylacetylene chromophores. Inorg Chim Acta 427:259–265

30.

Kirschner J, Bouzrati-Zerelli M, FouassierJ P, Becht JM, Klee JE, Lalevée J (2019) Silyl glyoxylates as high-performance photoinitiators for cationic and hybrid polymerizations: towards better polymer mechanical properties. J Polym Sci Polym Chem 57:1420–1429

31.

Škola O, Jašúrek B, Veselý D, Němec P (2016) Mechanical properties of polymer layers fabricated via hybrid free radical-cationic polymerization of acrylate, epoxide, and oxetane binders. Prog Org Coat 101:279–287

32.

Li M, Chen Y, Zhang H, Wang T (2010) A novel ferrocenium salt as visible light photoinitiator for cationic and radical photopolymerization. Prog Org Coat 68:234–239

33.

Mokbel H, Anderson D, Plenderleith R, Dietlina C, Morlet-Savary F, Dumur F, Gigmes D, Fouassier JP, Lalevée J (2019) Simultaneous initiation of radical and cationic polymerization reactions using the “G1” copper complex as photoredox catalyst: applications of free radical/cationic hybrid photopolymerization in the composites and 3D printing fields. Prog Org Coat 132:50–61

34.

Podsiadły R, Podemska K, Szymczak AM (2011) Novel visible photoinitiators systems for free-radical/cationic hybrid photopolymerization. Dyes Pigments 91:422–426

35.

Crivello JV (2007) A new visible light sensitive photoinitiator system for the cationic polymerization of epoxides. J Polym Sci Polym Chem 47:866–875

36.

Crivello JV (2007) Synergistic effects in hybrid free radical/cationic photopolymerizations. J Polym Sci Polym Chem 45:3759–3769

37.

Jiang B, Huang YD (2008) Quality inspection of laid fabric epoxy resins prepreg by near infrared spectroscopy. Compos A 39:712–717

38.

Li L, Wu Q, Li S, Wu P (2008) Study of the infrared spectral features of an epoxy curing mechanism. Appl Spectrosc 62:1129–1136PubMed

39.

Jiang B, Huang YD, He S, Xing LX, Wang HL (2015) Quality analysis and control strategies for epoxy resin and prepreg. TrAC Trends in Anal Chem 74:68–78

40.

Kocaarslan A, Tabanli S, Eryurek G, Yagci Y (2017) Near-infrared free-radical and free-radical-promoted cationic photopolymerizations by in-source lighting using upconverting glass. Angew Chem Int Edit 56:14507–14510

41.

Sari E, Moritz M, Liska R, Yagci Y (2019) Visible light induced free radical promoted cationic polymerization using acylsilanes. Prog Org Coat 132:139–143

42.

Dursun C, Degirmenci M, Yagci Y, Jockusch S, Turro NJ (2003) Free radical promoted cationic polymerization by using bisacylphosphine oxide photoinitiators: substituent effect on the reactivity of phosphinoyl radicals. Polymer 44:7389–7396

43.

Jockusch S, Koptyug IV, McGarry PF, Sluggett GW, Turro NJ, Watkins DM (1997) A steady-state and picosecond pump-probe investigation of the photophysics of an acyl and a bis(acyl)phosphine oxide. J Am Chem Soc 119:11495–11501

44.

Yagci Y, Borbely J, Schnabel W (1989) On the mechanism of a cylphosphine oxide promoted cationic polymerization. Eur Polym J 25:129–131

Title: Improvement on curing performance and morphology of E5I/TPGDA mixture in a free radical-cationic hybrid photopolymerization system
Authors: Ran Liu
Yuanyuan Xu
Jingwen Jia
Ping Chen
Fan Zhang
Lijun Zhang
Yu Chen
Publication date: 01-06-2020
Publisher: Springer Netherlands
Published in: Journal of Polymer Research / Issue 6/2020
Print ISSN: 1022-9760
Electronic ISSN: 1572-8935
DOI: https://doi.org/10.1007/s10965-020-02115-3

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