The influence of comonomer (2‐hydroxyethyl acrylate) and keto group on photocrosslinking property of arylidene polymers

Abstract

Two types of arylidene compounds were synthesized by reacting p‐hydroxybenzaldehyde with acetone [1,5‐bis(4‐hydroxyphenyl)penta‐1,4‐dien‐3‐one] (PBHP) and cyclohexanone [2,6‐bis(4‐hydroxybenzylidene)cyclohexanone] (HBC). 1,4‐Pentadien‐3‐one‐1‐p‐hydroxyphenyl‐5‐p‐phenyl methacrylate (PHPPMA) and 4‐{[‐3‐(4‐hydroxybenzylidene)‐2‐oxocyclohexylidene]methyl}phenyl acrylate (HBA) were prepared by reacting PBHP and HBC with methacryloyl chloride and acryloyl chloride in the presence of triethylamine, respectively. Copolymerization of different feed compositions of PHPPMA and HBA with 2‐hydroxyethyl acrylate (HEA) was carried out using a free‐radical solution polymerization technique in ethyl methyl ketone (MEK) using benzoyl peroxide (BPO). All the monomer and polymers were characterized by IR and NMR (1H/13C) spectroscopic techniques. The reactivity ratio of the monomers were obtained using Fineman–Ross (FR), Kelen–Tudos (KT), and extended Kelen–Tudos (exKT) methods. The photocrosslinking properties of the polymers were done using a UV absorption spectroscopy technique. Homopolymers of both the arylidene polymers shows similar trend towards the rate of photocrosslinking. The rate of photocrosslinking was enhanced when the cyclohexanone based arylidene monomer was copolymerized with HEA. Thermal stability and molecular weights (Mw and Mn) of the polymers were determined. © 2004 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 42: 3433–3444, 2004

Photocrosslinkable polymer based on 4-(3-(2,4-dichlorophenyl)-3-oxoprop-1-enyl) phenylacrylate: synthesis, reactivity ratio, and crosslinking studies

“…The copolymer composition was calculated using 1 HNMR spectroscopic technique [17]. The NMR spectrum of the poly(DCP-co-S) and poly(DCP-co-HEA) is presented in the Fig.…”

“…Several methods are available for finding the copolymer composition in the literature. The best known graphical methods are Fineman-Ross, Kelen-Tudos and extended Kelen-Tudos which is based on the trustable 1 HNMR spectroscopy [17]. Other methods used are elemental analysis, IR, etc.…”

Synthesis, characterization and properties of photoresponsive polymers comprising photocrosslinkable pendant chalcone moieties

“…13 C NMR spectra were recorded with respect to TMS as internal standard reference in CDCl 3 . A Mettler TA-3000 thermal analyser was used for TGA under nitrogen atmosphere.…”

“…Figures 2 and 3 show 1 H NMR spectra of poly(MPFSK) and poly(MPESK). 13 C NMR spectroscopy 13 C NMR chemical shift assignments were made from off-resonance decoupled spectra of the polymers. The 13 C NMR spectrum (Fig.…”

“…Polymers with photofunctional groups like the photopolymer containing 1,3-bis(4-hydroxyphenyl)-propenene, 12 poly(4-[5-(4-hydroxyphenyl)-3-oxopenta-1,4-dienyl]-phenyl-2-methacrylate), 13 polymers with bis(benzylidene)cyclohexanone units, 14 poly(dimethylmaleimide methacrylate), 15 poly(nonbornene derivative)s, 16 poly[(2 -4-bromobenzoyl)-4-styryloxyhexylmethacrylate], 17 poly(propylene fumarate), 18 methacrylate polymers comprising 2-cinnamoyloxyethoxybiphenyl side groups, 19 poly[(4-ethylphenoxy)-(phenoxy)phosphazene], 20 2-(dimethylmaleimido)-N-et-hylacrylamide, 21 poly(4-trimethylsilylmethyl styrene) thin films, 22 photosensitive poly(amic acid)s, 23 photochromic spiroxazine polymers containing a chalcone moiety, 24 poly(acryloyloxy styryl phenyl ketone) 25 and poly(2-trimethylsilyl-2-propyl methacrylate) 26 are some of the photoresists reported in the literature.…”