Synthesis, characterization, reactivity ratios by nuclear magnetic resonance spectroscopy, and application of (2,5‐Dichlorophenyl acrylate‐co‐glycidyl methacrylate) polymers as adhesives for the leather industry

Abstract

2,5-Dichlorophenyl acrylate (DPA)-co-glycidyl methacrylate (GMA) polymers having five different compositions were synthesized in 1,4-dioxane using benzoyl peroxide as a free-radical initiator at 70 Ϯ 0.5°C. Using 1 H-NMR spectroscopy, the composition of the two monomers in the copolymers was calculated by comparing the integral values of the aromatic and aliphatic proton peaks. The reactivity ratios were calculated by Fineman-Ross (r 1 ϭ 0.31 and r 2 ϭ 1.08), Kelen-Tudos (r 1 ϭ 0.40 and r 2 ϭ 1.15), and extended Kelen-Tudos (r 1 ϭ 0.39 and r 2 ϭ 1.16) methods. The nonlinear error-in-variables model was used to compare the reactivity ratios. The copolymers were characterized by 1 H and proton decoupled 13 C-NMR spectroscopes. Gel permeation chromatography was performed for estimating the M w and M n and M w /M n of the poly(DPA) and copolymers (DPA-co-GMA: 09 : 91 and 50 : 50). Thermal stability of the homo-and copolymers was estimated using TGA [poly(DPA) Ͼ DPA-co-GMA (50 : 50) Ͼ DPA-co-GMA (09:91)], while DSC was utilized for determining the glass transition temperature. T g increased with increased DPA content in the copolymer. The 50 : 50 mol % copolymer was chosen for curing with diethanolamine in chloroform. The cured resins were tested for the adhesive properties on leather at different temperatures (50, 90, 100, and 110°C). The resin cured at 50°C exhibited a maximum peel strength of 1.6 N/mm, revealing a good adhesive behavior.

Adhesives Based on Poly(glycidyl methacrylate‐co‐butyl acrylate) with Controlled Structure: Curing Behavior and Adhesion Properties on Metal Substrates

“…[ 20 ] Similarly, GMA was copolymerized by free radical polymerization with 2,5‐dichlorophenyl acrylate, to be used as adhesives employing diethanolamine (DEA), and tested for the adhesive properties on leather at different temperatures. [ 21 ] In the same way, for metal automotive applications, epoxy acrylate copolymers of acrylic resins are produced in solution with specific proportions of co‐monomer GMA. So depending on the desired properties, such as glass transition temperature ( T g ), melt viscosity, leveling, gelling time, and cross‐linking density, the monomers are selected; and the acrylic resin with the desired molecular weight is produced.…”