Imaging Science and Photochemistry ›› 2018, Vol. 36 ›› Issue (1): 82-88.DOI: 10.7517/j.issn.1674-0475.2018.01.008

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Synthesis of “Clickable” Acrylate Polymers and Their Thiol-alkyne Photocrosslinking Reaction

SHUI Xiaochuang, LIU Yu, WANG Yuechuan   

  1. State Key Laboratory of Polymer Materials Engineering, College of Polymer Science and Engineering, Sichuan University, Chengdu 610065, Sichuan, P. R. China
  • Received:2017-02-18 Revised:2017-04-05 Online:2018-01-15 Published:2018-01-15

Abstract: A acetylene functionalized acrylate monomer, 1-ethynylcyclohexyl acrylate(ECA), was prepared by the esterification of acryloyl chloride with 1-ethynyl 1-cyclohexanol. Then the acetylene functionalized polyacrylates PECA and PMA-co-PECA were synthesized through the free radical homopolymerization of ECA and copolymerization of ECA with methyl acrylate(MA).The structure of PECA and PMA-co-PECA were characterized by 1HNMR, FTIR and GPC. The results suggest that the triple bonds were completely retained, and the resulting polymers were soluble in common solvents such as chloroform, dimethyl sulfoxide, tetrahydrofuran, acetone, etc. The thiol-yne reaction between PMA-co-PECA and trimethylolpropane tri(3-mercaptopropionate) (TMTP) was monitored by real-time IR, suggesting that the acetylene bearing polymers can be rapidly photocrosslinked and functionalized by thiol-alkyne reaction, and the bulk tertairy group does not affect the reactivity of the thiol-yne reaction.The gel fraction of the yeilding network was found to be more than 90%.

Key words: acetylene bearing polyacrylate, free radical polymerization, thiol-yne click chemistry, photocrosslinking reaction