Synthesis and structure design of new bio-based elastomers via Thiol-ene-Click Reactions

Shafiullah Khan; Zhao Wang; Runguo Wang; Liqun Zhang

doi:10.1016/j.msec.2016.05.071

Synthesis and structure design of new bio-based elastomers via Thiol-ene-Click Reactions

Mater Sci Eng C Mater Biol Appl. 2016 Oct 1:67:554-560. doi: 10.1016/j.msec.2016.05.071. Epub 2016 May 18.

Authors

Shafiullah Khan¹, Zhao Wang², Runguo Wang³, Liqun Zhang⁴

Affiliations

¹ State Key Laboratory of Organic-Inorganic Composites and Key Laboratory of Beijing City for Preparation and Processing of Novel Polymer Materials, Beijing University of Chemical Technology, 100029 Beijing, PR China; Institute of Chemical Sciences, Gomal University, Dera Ismail Khan, KPK, Pakistan.
² State Key Laboratory of Organic-Inorganic Composites and Key Laboratory of Beijing City for Preparation and Processing of Novel Polymer Materials, Beijing University of Chemical Technology, 100029 Beijing, PR China; Department of Chemistry and Applied Biological Sciences, South Dakota School of Mines and Technology, Rapid City, SD 57701, United States. Electronic address: zhao.wang@sdsmt.edu.
³ State Key Laboratory of Organic-Inorganic Composites and Key Laboratory of Beijing City for Preparation and Processing of Novel Polymer Materials, Beijing University of Chemical Technology, 100029 Beijing, PR China.
⁴ State Key Laboratory of Organic-Inorganic Composites and Key Laboratory of Beijing City for Preparation and Processing of Novel Polymer Materials, Beijing University of Chemical Technology, 100029 Beijing, PR China. Electronic address: zhanglq@mail.buct.edu.cn.

PMID: 27287154
DOI: 10.1016/j.msec.2016.05.071

Abstract

The additions of 2-mercaptoethanol to (S)-(-)-limonene via click reaction is described as an adaptable and efficient way to obtain alcohol functionalized renewable monomer for the synthesis of new cross-linkable bio-based elastomers. Thiol first reacted with the limonene endocyclic double bond and then reacted with the exocyclics double bond to form the difunctional monomer. The structure of the monomer was determined by using FTIR, (1)H NMR and mass spectrometry. Thermal Gravimetric Analysis (TGA) and Differential Scanning Calorimetrys (DSC) characterization exposed that this monomer could be used to synthesize elastomers with excellent and adaptable thermal properties. The molecular weight of the synthesized elastomer could reach 186kDaa via melting polycondensation route and the structure-properties relationship was deliberated. Finally, these elastomers were mixed with dicumyl peroxide (DCP) to form cross-linked elastomers with certain mechanical property, and the gel contents of the elastomers were confirmed by using Soxhlet extraction method.

Keywords: (S)-(−)-limonene; Bio-based elastomers; Thermal properties; Thiol-ene-click.

MeSH terms

Benzyl Compounds / chemistry
Click Chemistry / methods*
Cross-Linking Reagents / chemistry
Cyclohexenes / chemistry*
Elastomers* / chemical synthesis
Elastomers* / chemistry
Limonene
Mercaptoethanol / chemistry*
Terpenes / chemistry*

Substances

Benzyl Compounds
Cross-Linking Reagents
Cyclohexenes
Elastomers
Terpenes
Mercaptoethanol
Limonene
dicumyl peroxide