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Chemical modification of polydienes in latex medium: Study of epoxidation and ring opening of oxiranes
Author(s) -
Derouet Daniel,
MulderHoudayer Stéphanie,
Brosse JeanClaude
Publication year - 2004
Publication title -
journal of applied polymer science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.575
H-Index - 166
eISSN - 1097-4628
pISSN - 0021-8995
DOI - 10.1002/app.20809
Subject(s) - sn2 reaction , polymer chemistry , reagent , nucleophilic substitution , chemistry , reaction mechanism , natural rubber , ring (chemistry) , epoxide , grafting , materials science , organic chemistry , polymer , catalysis
Abstract Referring to previous work carried out in organic solvents, a study of the action of nucleophilic reagents on epoxidized units of 1,4‐epoxidized polyisoprene (synthetic polyisoprene or natural rubber) was performed in latex medium. Among the considered reagents, dialkylphosphate and ammonium diethyldithiophosphate demonstrated the ability to add under these reaction conditions on epoxidized units according to a SN2 substitution with an oxirane ring‐opening mechanism. A systematic study was performed with dibutylphosphate that was shown to be very reactive. Grafting of phosphorated groups along polyisoprene chains was carried out via reaction of the acidic function (P‐OH) of the phosphate with oxirane rings previously created on a 1,4‐polyisoprene backbone. The prominent role of latex pH on the reaction was shown. © 2004 Wiley Periodicals, Inc. J Appl Polym Sci 95: 39–52, 2005