Free radical synthesis of α,ω‐primary amino functionalized polyisoprene through the functional thermal inferter [bis(N‐(2‐phthalimidoethyl)piperazine)]thiuram disulfide
- 1 January 1994
- journal article
- research article
- Published by Wiley in Macromolecular Chemistry and Physics
- Vol. 195 (1) , 243-251
- https://doi.org/10.1002/macp.1994.021950122
Abstract
The primary amino functional iniferter [bis(N(2‐phthalimidoethyl)piperazine)]thiuram disulfide (PEPTD) was synthesied and characterized. Thermal polymerization of isoprene in the presence of the initiator afforded α,ω‐functionalized polyisoprene with primary amino end‐groups after cleavage of the phthalimido group with butylamine. The kinetics of polymerization of isoprene using this iniferter was studied at 80, 85, 90 and 100°C. Interestingly, isoprene showed a complex kinetic behavior. The different parameters, related to initiation, chain transfer and primary radical termination reactions, as well as the constants for thermal decomposition of the initiator, were determined. From the Arrhenius plot, the activation energy of the overall decomposition constant of PEPTD (2 f kd) was calculated to be 110 kJ/mol. The functionality of the telechelics was examined by GPC.Keywords
This publication has 10 references indexed in Scilit:
- Functionalization of PMMA by a functional “iniferter”: Kinetics of polymerization of MMA using N,N′‐diethyl‐N,N′‐bis(2‐hydroxyethyl) thiuram disulfideJournal of Polymer Science Part A: Polymer Chemistry, 1989
- Synthesis of aminotelechelic polymers with the redox system TiCl3NH2OH in hydrochloric aqueous phase: 3. Polymerization of methylacrylate. relation functionality/molecular weight/yieldPolymer, 1981
- Synthesis of aminotelechelic polymers with the redox system TiCl3NH2OH in hydrochloric aqueous phase: 2. Polymerization of methylmethacrylate. Relation functionality/molecular weight/yieldPolymer, 1981
- Polymerization of methylmethacrylate in presence of tetramethylthiuramdisulphideEuropean Polymer Journal, 1978
- Gabriel‐Synthese primärer AmineAngewandte Chemie, 1968
- Study of the activity of some sulfur compounds in the modification of vulcanizates by vinyl monomersJournal of Polymer Science Part C: Polymer Symposia, 1967
- Bulk polymerization of isoprene: Kinetic constants from the dead‐end theoryJournal of Polymer Science, 1960
- Organic Disulfides as Initiators of Polymerization. Part II1Journal of the American Chemical Society, 1958
- Organic Disulfides as Initiators of Polymerization: Tetramethylthiuram DisulfideJournal of the American Chemical Society, 1955
- Bis‐type modifiers in polymerization. I. Behavior of various disulfides in bulk styrene polymerizationJournal of Polymer Science, 1955