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Functional Polymers. III. Endcapping and Substitution on Polymers with Compounds Containing Ultraviolet-Absorbing Groups

Bailey, D. and Tirrell, D. and Vogl, O. (1978) Functional Polymers. III. Endcapping and Substitution on Polymers with Compounds Containing Ultraviolet-Absorbing Groups. Journal of Macromolecular Science, Part A, 12 (5). pp. 661-699. ISSN 1060-1325. doi:10.1080/00222337808066585.

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Endcapping of oligo(oxyethylene) glycols was carried out by transesterification of methyl N,N-dimethylaminobenzoate with sodium methoxide as the catalyst or by the reaction of sodium salicylate with the ditosyl ester of the oligo(oxyethyl-ene) glycols. Several other common reactions were tried for the endcapping of the oligo(oxyethylene) glycols but were found to be either more cumbersome or unsuccessful. All products were obtained in high yield and high purity. The reactions of tetraalkylammonium carboxylates with aliphatic halides were found to be very general and mild reactions for the preparation of esters in high yield and high purity. It was found that these reactions could be utilized for the preparation of esters on polymers even if the carboxylate group was directly attached to the polymer chain. It was also demonstrated that the aliphatic halide group could be on the polymer, as in the case of polyepichlorohydrin. Copolymers of epichlorohydrin and glycidyl N,N-dimethylaminobenzoate with up to 90% glycidyl benzoate as the comonomer were prepared, and poly(tetra-butylammonium methacrylate) was effectively transformed with 4-(2-bromoethoxy)-2-hydroxybenzophenone into the corresponding ester. The products were characterized by the usual spectral means.

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Tirrell, D.0000-0003-3175-4596
Additional Information:© 1979 Marcel Dekker. Accepted by editor November 27, 1977; Received for publication December 10, 1977. Financial support .for this work was provided by the U. S. Army Research Office, Department of the Army, Grants DA-ARO-D-31-124-73-G60, DAHC-04-74-G0037, and DAH-19-72-G-0002. We would like to express our appreciation to Dr. Eugene Sporn for his continuous encouragement and support. This paper was written while one of us (O. V.) was on sabbatical leave and the recipient of the Award of the Alexander von Mumboldt Stiftung at the Institute of Organic Chemistry, Free University of Berlin.
Funding AgencyGrant Number
Army Research Office (ARO)DA-ARO-D-31-124-73-G60
Army Research Office (ARO)DAHC-04-74-G0037
Army Research Office (ARO)DAH-19-72-G-0002
Alexander von Humboldt StiftungUNSPECIFIED
Issue or Number:5
Record Number:CaltechAUTHORS:BAIjmsca1978
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Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:55061
Deposited By: Anne Hormann
Deposited On:20 Feb 2015 21:18
Last Modified:10 Nov 2021 20:41

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