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Title: Characterization and evaluation of polymers containing herbicides as pendent side chains
Authors: Wright State University. Department of Chemistry.
Mobility and Environmental Systems Laboratory (U.S.)
Aquatic Plant Control Research Program (U.S.)
Harris, Frank Wayne, 1942-
Keywords: Herbicides
Aquatic plants
Chemical control
Issue Date: Apr-1977
Publisher: Environmental Laboratory (U.S.)
Engineer Research and Development Center (U.S.)
Description: Contract Report
Abstract: The syntheses of five vinyl monomers containing fenac, i.e., vinyl 2,3,6-trichlorophenylacetate, 2-acryloyloxyethyl 2,3,6-trichlorophenylacetate, 4-acryloyloxybutyl 2,3,6-trichlorophenylacetate, 4-vinyloxybutyl 2,3,6-trichlorophenylacetate, and 2-methacryloyloxyethyl 2,3,6-trichlorophenylacetate, were carried out. These monomers were polymerized by bulk- and solution-free-radical techniques to afford the corresponding polymers. A study of the hydrolysis of poly(vinyl 2,4-dichlorophenoxyacetate), poly(2-acryloyloxyethyl 2,4,-dichlorophenoxyacetate), an 87:13 copolymer of 2-acryloyloxyethyl 2,4-dichlorophenoxyacetate and trimethylamine methacrylimide, poly(1-methyl-2-acryloyloxyethyl 2,4-dichlorophenoxyacetate), and poly(4-acryloyloxybutyl 2,4-dichlorophenoxyacetate) at pH 7 was completed. The hydrolysis of poly(vinyl 2,3,6-trichlorophenylacetate), poly(vinyl 2,4-dichlorophenoxyacetate), poly(2-acryloyloxyethyl 2,4-dichlorophenoxyacetate), and a 75:25 copolymer of 2-acryloyloxyethyl 2,4-dichlorophenoxyacetate and trimethylamine methacrylimide at pH 8.08 was also investigated. The results of these studies showed that only copolymers containing hydrophilic residues will undergo hydrolysis. Hence, a detailed study of the copolymerization of the monomers containing 2,4-dichlorophenoxyacetic acid (2,4-D) with acrylic acid, methacrylic acid, N-vinyl-2-pyrrolidone, and trimethylamine methacrylimide was carried out. All of the resulting copolymers underwent hydrolysis in water with a pH of 8 at 30°C. The rate of hydrolysis depended on the type and amount of the hydrophilic comonomer used. Samples of three copolymers of 2-cryloyloxyethyl 2,4-dichlorophenoxyacetate containing 5% methacrylic acid, 10% methacrylic acid, and 35% trimethylamine methacrylimide, respectively, were prepared for preliminary field testing. Fenac was also physically incorporated in polyethylene pellets to provide an additional formulation for field evaluation.
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