Xanthate-derived mercaptophosphonates for thiol-ene modification of styrene-butadiene rubber. (15th May 2021)

• Record Type: Journal Article
• Authors: Coutelier, Olivier; Blidi, Issam; Destarac, Mathias
• Is Part Of: European polymer journal. Volume 151(2021)
• Publication Date: 2021-05-15
• Subjects: Thiol-ene -- SBR -- RAFT -- Xanthate -- Phosphonate; Polymers -- Periodicals; Polymerization -- Periodicals; Polymères -- Périodiques; Polymérisation -- Périodiques; Polymerization; Polymers; Periodicals; Electronic journals; 547.705
• DOI: 10.1016/j.eurpolymj.2021.110419
• Languages: English
• ISSNs: 0014-3057

Abstract

Graphical abstract: Abstract: The functionalization of elastomers by phosphonate groups remains relatively unexplored considering the great potential these polymers would represent for applications. In this paper, thiol-functional oligophosphonates were designed and coupled by a thiol-ene reaction to a styrene-butadiene rubber (SBR). We adopted a RAFT methodology with dimethyl vinylphosphonate (DMVP) and a high-temperature thermolysable xanthate, to afford the monophosphonate DMVP-SH and P(DMVP)5 -SH, a mercapto(oligophosphonate) of DPn = 5. We conducted a comparative study of the thiol-ene coupling reaction of DMVP-SH and P(DMVP)5 -SH with a SBR for different degrees of functionalization. We observed that P(DMVP)5 -SH was as reactive as DMVP-SH. Although only limited grafting could be achieved without alteration of the SBR structure by radical intercoupling reactions, P(DMVP)5 -SH was found superior to DMVP-SH for increasing the phosphonate content of the SBR thanks to its oligophosphonate character.