Reversible addition–fragmentation chain transfer polymerization of 2-chloro-1,3-butadiene

Nikki Pullan; Max Liu; Paul D. Topham

doi:10.1039/C3PY21151G

Reversible addition–fragmentation chain transfer polymerization of 2-chloro-1,3-butadiene

Nikki Pullan, Max Liu, Paul D. Topham

Chemical Engineering & Applied Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

Controlled polymerization of 2-chloro-1,3-butadiene using reversible addition–fragmentation chain transfer (RAFT) polymerization has been demonstrated for the first time. 2-Chloro-1,3-butadiene, more commonly known as chloroprene, has significant industrial relevance as a crosslinked rubber, with uses ranging from adhesives to integral automotive components. However, problems surrounding the inherent toxicity of the lifecycle of the thiourea-vulcanized rubber have led to the need for control over the synthesis of poly(2-chloro-1,3-butadiene). To this end, four chain transfer agents in two different solvents have been trialed and the kinetics are discussed. 2-Cyano-2-propylbenzodithioate (CPD) is shown to polymerize 2-chloro-1,3-butadiene in THF, using AIBN as an initiator, with complete control over the target molecular weight, producing polymers with low polydispersities (Mw/Mn < 1.25 in all cases).

Original language	English
Pages (from-to)	2272-2277
Number of pages	6
Journal	Polymer Chemistry
Volume	4
Issue number	7
Early online date	29 Jan 2013
DOIs	https://doi.org/10.1039/C3PY21151G https://doi.org/10.1039/c3py21151g
Publication status	Published - 7 Apr 2013

Bibliographical note

Creative Commons attribution

Funding: Pera Technology, the European Commission and the EPSRC (Robinson Brothers Ltd). and through funding as part of the Framework Programme 7 SafeRubber project (243756).

Electronic supplementary information (ESI) available: Scheme showing CB
synthesis, GPC traces taken periodically throughout each RAFT polymerization
and spectral data for PCB synthesized using CPD CTA. See DOI:
10.1039/c3py21151g

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Reversible addition-fragmentation chain transfer polymerization
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Reversible addition-fragmentation chain transfer polymerization of 2-chloro-1, 3-butadiene
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title = "Reversible addition–fragmentation chain transfer polymerization of 2-chloro-1,3-butadiene",

abstract = "Controlled polymerization of 2-chloro-1,3-butadiene using reversible addition–fragmentation chain transfer (RAFT) polymerization has been demonstrated for the first time. 2-Chloro-1,3-butadiene, more commonly known as chloroprene, has significant industrial relevance as a crosslinked rubber, with uses ranging from adhesives to integral automotive components. However, problems surrounding the inherent toxicity of the lifecycle of the thiourea-vulcanized rubber have led to the need for control over the synthesis of poly(2-chloro-1,3-butadiene). To this end, four chain transfer agents in two different solvents have been trialed and the kinetics are discussed. 2-Cyano-2-propylbenzodithioate (CPD) is shown to polymerize 2-chloro-1,3-butadiene in THF, using AIBN as an initiator, with complete control over the target molecular weight, producing polymers with low polydispersities (Mw/Mn < 1.25 in all cases).",

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note = "Creative Commons attribution Funding: Pera Technology, the European Commission and the EPSRC (Robinson Brothers Ltd). and through funding as part of the Framework Programme 7 SafeRubber project (243756). Electronic supplementary information (ESI) available: Scheme showing CB synthesis, GPC traces taken periodically throughout each RAFT polymerization and spectral data for PCB synthesized using CPD CTA. See DOI: 10.1039/c3py21151g",

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N2 - Controlled polymerization of 2-chloro-1,3-butadiene using reversible addition–fragmentation chain transfer (RAFT) polymerization has been demonstrated for the first time. 2-Chloro-1,3-butadiene, more commonly known as chloroprene, has significant industrial relevance as a crosslinked rubber, with uses ranging from adhesives to integral automotive components. However, problems surrounding the inherent toxicity of the lifecycle of the thiourea-vulcanized rubber have led to the need for control over the synthesis of poly(2-chloro-1,3-butadiene). To this end, four chain transfer agents in two different solvents have been trialed and the kinetics are discussed. 2-Cyano-2-propylbenzodithioate (CPD) is shown to polymerize 2-chloro-1,3-butadiene in THF, using AIBN as an initiator, with complete control over the target molecular weight, producing polymers with low polydispersities (Mw/Mn < 1.25 in all cases).

AB - Controlled polymerization of 2-chloro-1,3-butadiene using reversible addition–fragmentation chain transfer (RAFT) polymerization has been demonstrated for the first time. 2-Chloro-1,3-butadiene, more commonly known as chloroprene, has significant industrial relevance as a crosslinked rubber, with uses ranging from adhesives to integral automotive components. However, problems surrounding the inherent toxicity of the lifecycle of the thiourea-vulcanized rubber have led to the need for control over the synthesis of poly(2-chloro-1,3-butadiene). To this end, four chain transfer agents in two different solvents have been trialed and the kinetics are discussed. 2-Cyano-2-propylbenzodithioate (CPD) is shown to polymerize 2-chloro-1,3-butadiene in THF, using AIBN as an initiator, with complete control over the target molecular weight, producing polymers with low polydispersities (Mw/Mn < 1.25 in all cases).

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Reversible addition–fragmentation chain transfer polymerization of 2-chloro-1,3-butadiene

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