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CO 2 ‐derived latent nitrogen nucleophiles for controlled cross‐linking of brominated poly(isobutylene‐ co ‐isoprene)
Author(s) -
Faba Michael A.J.,
Parent J. Scott,
Whitney Ralph A.
Publication year - 2011
Publication title -
polymer engineering and science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.503
H-Index - 111
eISSN - 1548-2634
pISSN - 0032-3888
DOI - 10.1002/pen.21941
Subject(s) - isobutylene , nucleophile , thermal decomposition , isoprene , thermogravimetric analysis , chemistry , carbamate , polymer chemistry , organic chemistry , polymer , materials science , copolymer , catalysis
New methods for preparing thermoset elastomer products from brominated poly(isobutylene‐ co ‐isoprene) (BIIR) are described, wherein control of cross‐linking dynamics is gained using latent forms of ammonia, primary amines, and cyclic amidines. BIIR cross‐linking by repeated alkylation of standard nitrogen nucleophiles is too rapid at standard polymer processing temperatures, whereas CO 2 ‐derived salts are shown to be sufficiently inactive under these conditions to support conventional BIIR compounding. Examples include the carbonate, bicarbonate and carbamate salts of ammonia; carbamate and carbamate esters of hexadecyl amine; and the bicarbonate salt of 1,8‐diazabicyclo[5.4.1]undec‐7‐ene. Thermal decomposition of these latent curatives releases CO 2 and the desired nucleophile to support high cross‐linking rates and yields at standard cure temperatures. Thermogravimetric analysis of salt decomposition, rheological measurements of cross‐link density, and spectroscopic analysis of polymer dehydrohalogenation products are used to define the relationship between latent nucleophile activation and BIIR cure dynamics. POLYM. ENG. SCI., 2011. © 2011 Society of Plastics Engineers.