Influence of the comonomers (styrene and methyl acrylate) on the rate of photocrosslinking of 4‐{[‐3‐(4‐hydroxybenzylidene)‐2‐oxocyclohexylidene]methyl}‐ phenyl acrylate

Abstract

[2,6-Bis(4-hydroxybenzylidene)cyclohexanone] (HBC) was prepared by reacting cyclohexanone and phydroxybenzaldehyde in the presence of acid catalyst. Acrylated derivative of HBC, 4-{[-3-(4-hydroxybenzylidene)-2-oxocyclohexylidene]methyl}phenyl acrylate (HBA), was prepared by reacting HBC with acryloyl chloride in the presence of triethylamine. Copolymers of HBA with styrene (S) and methyl acrylate (MA) of different feed compositions were carried out by solution polymerization technique by using benzoyl peroxide (BPO) under nitrogen atmosphere. All monomers and polymers were characterized by using IR and NMR techniques. Reactivity ratios of the monomers present in the polymer chain were evolved by using Finnman-Ross (FR), Kelen-Tudos (KT), and extended Kelen-Tudos (ex-KT) methods. Average values of reactivity were achieved by the following three methods: r 1 (S) ϭ 2.36 Ϯ 0.45 and r 2 (HBA) ϭ 0.8 Ϯ 0.31 for poly(S-co-HBA); r 1 ϭ 1.62 Ϯ 0.06 (MA); and r 2 ϭ 0.12 Ϯ 0.07 (HBA) for poly(MA-co-HBA). The photocrosslinking property of the polymers was done by using UV absorption spectroscopic technique. The rate of photocrosslinking was enhanced compared to that of the homopolymers, when the HBA was copolymerized with S and MA. Thermal stability and molecular weights (M w and M n ) were determined for the polymer samples.

Synthesis and characterization of novel polyurethanes based on 2,6‐bis(4‐hydroxybenzylidene) cyclohexanone hard segments

“…The chalcone diol was prepared as per the published report. 18 The structure of BHBC was established by Fourier transform infrared (FTIR) spectroscopy, 1 H-NMR and 13 C-NMR spectral data. The synthesized PUs were further characterized by ultraviolet-visible (UV-vis) spectroscopy, fluorescence, FTIR spectroscopy, 1 H-NMR, 13 C-NMR, differential thermal analysis (DTA)/thermogravimetric analysis (TGA), and X-ray diffraction techniques.…”

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

“…The procedure given in our publication24 was adopted for the synthesis of HBC; 24.4 g (0.2 mol) of p ‐hydroxybenzaldehyde reacted with 11.4 mL (0.1 mol) of cyclohexanone gave HBC: yield = 28.3 g (92.5%). 1 H NMR (CDCl 3 ): δ = 10.2 (2H, b, phenolic OH), 7.2 (1H, s, vinyl type CH), 7.4 (1H, s, vinyl type CH), 7.5–7.8 (8H, m, aromatic protons) and 2.2 (6H, m, cyclohexanone ring protons).…”

“…The procedure given in our article24 was used for the synthesis of HBA; 10.1 g (0.03 mol) of HBC, 4.9 mL (0.035 mol) of triethylamine, and 2.7 mL (0.03 mol) of acryloyl chloride was used for the preparation of HBA: yield = 10.9 g (92%); m.p. : 237–238 °C.…”

Acrylate polymers of triazine containing chalcone moiety: Synthesis, characterization, reactivity ratio and photocrosslinking studies

“…Chalcone has been studied extensively due to its strong photoreactivity and high amount of photocrosslinking when irradiated with UV light in the absence of photosensitizers, and is utilized in a variety of polymer applications. 12 Different polymer compounds based on acrylates, 13 acrylamides, 14 urethane, 15 and even plant based 16 have been prepared by researcher having photosensitive moiety and these polymers were readily undergoing crosslinking and then used in many areas.…”