Tan, J., Li, C., Li, H., Zhang, H., Gu, J., Zhang, B., Zhang, H. and Zhang, Q. (2015) Water-Borne Thiol-Isocyanate Click Chemistry in Microfluidics: Rapid and Energy-Efficient Preparation of Uniform Particles. Polymer Chemistry, 6, 4366-4373.
http://pubs.rsc.org/en/Content/ArticleLanding/2015/PY/C5PY00412H#!divAbstract
https://doi.org/10.1039/C5PY00412H

has been cited by the following article:

• TITLE: Synthesis and Properties of Organic-Inorganic Hybrid Porous Polymers Obtained with Click Addition Reactions of Thiol-Functionalized Random Type Silsesquioxane by and Diacrylate or Diisocyanate Compounds

  AUTHORS: Tomoharu Miyanaga, Naofumi Naga

  KEYWORDS: Silsesquioxane, Thiol, Diacrylate, Diisocyanate, Gel, Porous Polymer, Morphology

  JOURNAL NAME: Open Journal of Polymer Chemistry, Vol.10 No.1, February 19, 2020

  ABSTRACT: Organic-inorganic hybrid network polymers have been synthesized by addition reaction of a thiol-functionalized random type silsesquioxane (SQ109) and alkyl diacrylate or diisocyanate compounds. Thiol-ene reaction of SQ109 and 1,4-butanediol diacrylate (BDA) successfully yield porous polymer in toluene initiated by azobis(isobutyronitrile) (AIBN) at 60°C. Morphology of the porous polymers was composed by connected globules, and the diameter of the globules decreased with increasing in the monomer concentration of the reaction system. By contrast, the reaction with 1,6-hexanediol diacrylate or 1,5-hexadiene yielded homogeneous clear gels. Thermal analyses of SQ109-BDA porous polymers indicated that thermal degradation of ester groups of BDA in the polymer network occurred at around 300°C. The porous polymer was also obtained by the reaction using a photo-initiator (Irugacure184) at room temperature, and showed higher Young’s modulus than the corresponding porous polymer obtained with the reaction with AIBN due to the small size of the globules. Young’s modulus of SQ109-BDA porous polymer increased with increasing in the monomer concentration of the reaction systems. Thiolisocyanate addition reactions between SQ109 and hexamethylene diisocyanate (HDI) or methylenediphenyl 4,4’-diisocyanate (MDI) were investigated to obtain network polymers. The reactions in toluene yielded the corresponding homogeneous clear gels. By contrast the reactions in a mixed solvent of toluene (50 vol.%) and N,N-dimethylformamide (50 vol.%) produced porous polymers. The morphology of the porous polymers was composed by connected globules or aggregated particles. The size of globules and particles in the SQ109-HDI porous polymers was larger than those in the SQ109-MDI porous polymers. Thermal degradation of SQ109-HDI and SQ109-MDI porous polymers started at round 260°C and showed endothermic peak at around 350°C derived from degradation of thio-urethane bond.