Modification of copolymers using nucleophilic reactions between glycidyl methacrylate and 9-anthracene carboxylic acid

Mohammad Hossein Nasirtabrizi,Aiyoub Parchehbaf Jadid,Sona Khodabandlou,Laya Zargin

doi:10.1007/s40090-014-0006-8

Mohammad Hossein Nasirtabrizi, Aiyoub Parchehbaf Jadid + Show 2 more

Open Access

https://doi.org/10.1007/s40090-014-0006-8

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Abstract

Epoxide ring opening reaction is a route that explains the chemical modification of glycidyl methacrylate (GMA) polymers with nucleophilic reagent containing hydroxyl, carboxyl or amine groups. In this work copolymers of GMA have been modified by incorporation of bulky 9-anthracene carboxylic acid groups. The glycidyl methacrylate polymers were prepared by radical copolymerization of GMA methyl, methacrylate, ethyl methacrylate, methyl acrylate and butyl acrylate mixtures. The polymers were modified through epoxy functional groups in two steps: (i) the glycidyl methacrylate copolymers were dissolved in N,N-di-methyl formamide; (ii) 9-anthracene carboxylate salt was added to the copolymers solutions prepared in step (i). The structure of all the resulting polymers was characterized and confirmed by FT-IR and 1H-NMR spectroscopic techniques. The presence of bulky 9-anthracene carboxylate groups in polymer side chain leads to different applications in the polymer industry and also a series of novel modified polymers are obtained.

Highlights

Glycidyl methacrylate (GMA) has a high tendency for homopolymerization and copolymerization with other monomers [1,2,3]
In this work copolymers of glycidyl methacrylate (GMA) have been modified by incorporation of bulky 9-anthracene carboxylic acid groups
The polymers were modified through epoxy functional groups in two steps: (i) the glycidyl methacrylate copolymers were dissolved in N,N-di-methyl formamide; (ii) 9-anthracene carboxylate salt was added to the copolymers solutions prepared in step (i)

Summary

Introduction

Glycidyl methacrylate (GMA) has a high tendency for homopolymerization and copolymerization with other monomers [1,2,3]. The interest in glycidyl methacrylate copolymers has been continuously growing, due to their successful application in various industrial processes [7]. Copolymers of glycidyl methacrylate are commercially available, bearing reactive epoxide groups; these epoxide groups present in the polymer chain can undergo an opening reaction with nucleophilic reagents which contain hydroxyl, carboxyl, trisyl or amine groups [8,9,10,11,12,13,14,15]. There already exist examples of some interesting polymers that are modified by 9-anthracene carboxylic acid group [19]. These anthracene groups could take part in cycloaddition reaction with other functional groups such as anhydrides and quinones. The thermal properties of the obtained polymers have been studied

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Results and discussion

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Conclusion