Synthesis of joint-linker type gels and porous polymers by addition reactions of multi-functional thiol and alkyl diacrylate, diisocyanate compounds

Naofumi Naga, Ryo Michida, Shuntaro Kudo, Yosuke Nagami, Kazumasa Moriyama, Hassan Nageh, Hidemitsu Furukawa, Tamaki Nakano

Research output: Contribution to journalArticle

Abstract

Joint-linker type gels and porous polymers have been synthesized by addition reaction of multi-functional thiol and alkyl diacrylate or diisocyanate compounds. The reaction of multi-functional thiol, 1,3,5-tris(3-mercaptobutyloxethyl)-1,3,5-triazine-2,4,6- (1H,3H,5H)-trione (3T) or pentaerythritol tetrakis(3-mercaptobutylate) (PTMB), as joint molecule, and alkyl diacrylate, 1,4-butanediol diacrylate, 1,6-hexanediol diacrylate, 1,9-nonanediol diacrylate, as linker molecule in toluene successfully yield the corresponding gels. Network structure of the gels was quantitatively characterized by means of a scanning microscopic light scattering. The obtained gels formed homogeneous network structure with 1.2–2.0 nm of mesh. Mechanical properties of the gels were investigated by compression test. Increasing of the monomer concentration increased Young's modulus and breaking stress of the gels. The gels composed of PTMB showed high Young's modulus and breaking stress than the gels composed of 3T. The gels were also prepared in propylene carbonate or dimethyl sulfoxide (DMSO), and the gels prepared in DMSO showed high Young's modulus. The addition reaction of 3T or PTMB and diisocyanate compound, hexamethylene diisocyanate (HDI) or 1,12-diisocyanatododecane (DDI), in toluene yielded porous polymers induced by phase separation during the polymerization. The porous structure was formed by connected globules about 5–10 μm diameter. The reactions of 3T, PTMB with HDI, DDI in tetrahydrofuran (THF) or N,N’-dimethylformamide (DMF) yielded transparent gels, and the gels prepared in DMF showed higher Young's modulus than those prepared in THF.

Original languageEnglish
Pages (from-to)153-162
Number of pages10
JournalMaterials Today Communications
Volume18
DOIs
Publication statusPublished - 2019 Mar 1

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Addition reactions
Sulfhydryl Compounds
Polymers
Gels
Elastic moduli
Dimethylformamide
Dimethyl sulfoxide
Toluene
Dimethyl Sulfoxide
Molecules
Phase separation
Light scattering
Propylene
Carbonates
Monomers
Polymerization

Keywords

  • Diacrylate
  • Diisocyanate
  • Gel
  • Mechanical property
  • Network structure
  • Porous polymer
  • Thiol

ASJC Scopus subject areas

  • Materials Science(all)
  • Mechanics of Materials
  • Materials Chemistry

Cite this

Synthesis of joint-linker type gels and porous polymers by addition reactions of multi-functional thiol and alkyl diacrylate, diisocyanate compounds. / Naga, Naofumi; Michida, Ryo; Kudo, Shuntaro; Nagami, Yosuke; Moriyama, Kazumasa; Nageh, Hassan; Furukawa, Hidemitsu; Nakano, Tamaki.

In: Materials Today Communications, Vol. 18, 01.03.2019, p. 153-162.

Research output: Contribution to journalArticle

Naga, Naofumi ; Michida, Ryo ; Kudo, Shuntaro ; Nagami, Yosuke ; Moriyama, Kazumasa ; Nageh, Hassan ; Furukawa, Hidemitsu ; Nakano, Tamaki. / Synthesis of joint-linker type gels and porous polymers by addition reactions of multi-functional thiol and alkyl diacrylate, diisocyanate compounds. In: Materials Today Communications. 2019 ; Vol. 18. pp. 153-162.
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AU - Naga, Naofumi

AU - Michida, Ryo

AU - Kudo, Shuntaro

AU - Nagami, Yosuke

AU - Moriyama, Kazumasa

AU - Nageh, Hassan

AU - Furukawa, Hidemitsu

AU - Nakano, Tamaki

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KW - Diacrylate

KW - Diisocyanate

KW - Gel

KW - Mechanical property

KW - Network structure

KW - Porous polymer

KW - Thiol

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