Synthesis of Nanoporous Crosslinked Poly(Acryl‐N‐cyclohexyl Amide‐co‐Ethylene Glycol Dimethacrylate) by Thermal Degradation of Poly(Acryl‐N,N′‐dicyclohexylurea‐co‐Ethylene Glycol Dimethacrylate)

Abstract

Crosslinked unswellable copolymers of acryl‐dicyclohexylurea (A‐DCU) with ethylene glycol dimethacrylate (EDMA) at monomer‐to‐monomer ratios in the feed: 0.3/0.7; 0.5/0.5; 0.7/0.3; 0.8/0.2 were prepared by free radical copolymerization in butanone in the presence of 1% of benzoyl peroxide. The reaction was performed up to high conversion yielding 99–100% of copolymer. Copolymers regardless of the ratio of comonomers in the feed decompose thermally by a two‐step mechanism under the separation of almost quantitative yield of cyclohexylisocyanate (C₆H₁₁NCO). Residues after the removal of C₆H₁₁NCO are thermally stable nanoporous crosslinked copolymers of acryl‐cyclohexylamide (A‐CHA) with EDMA which decompose by a one‐step mechanism between 300 and 450°C. In an attempt to compare the thermal properties of nanoporous poly(A‐CHA‐co‐EDMA) with a nonporous model compound prepared by copolymerization of A‐CHA with EDMA it was found that both compounds have almost the same thermal stability as proved by thermogravimetric analysis.

Keywords:

• Acryl‐N,N′‐dicyclohexylurea
• Poly(acryl‐N,N′‐dicyclohexylurea‐co‐ethylene glycol dimethacrylate)
• Acryl‐N‐cyclohexylamide
• Poly(acryl‐N‐cyclohexylamide‐co‐ethylene glycol dimethacrylate)
• Thermal properties
• Thermal degradation
• Nanoporous crosslinked copolymers

Acknowledgment

The Ministry of Science and Technology of Croatia supported this work.