Cyanate ester resins containing pentadecyl-substituted cyclohexyl moiety: synthesis, curing and structure-property relationship

TitleCyanate ester resins containing pentadecyl-substituted cyclohexyl moiety: synthesis, curing and structure-property relationship
Publication TypeJournal Article
Year of Publication2013
AuthorsKulkarni, AD, Tawade, BV, Wadgaonkar, PP
JournalHigh Performance Polymers
Volume25
Issue3
Pagination278-286
Date PublishedMAY
ISSN0954-0083
Keywords(pentadecyl substituted) cyclohexyl, curing, cyanate ester resin, thermosets
Abstract

Cyanate ester (CE) monomers containing pentadecyl-substituted cyclohexyl moieties such as 1,1-bis(4-cyanatophenyl) 3-pentadecylcyclohexane and 1,1-bis(4-cyanatophenyl) cyclohexane were synthesized and characterized by Fourier transform infrared, proton-nuclear magnetic resonance (H-1-NMR) and carbon-nuclear magnetic resonance (C-13-NMR) spectroscopies as well as differential scanning calorimetry (DSC). Both 1,1-bis(4-cyanatophenyl) 3-pentadecylcyclohexane and 1,1-bis(4-cyanatophenyl) cyclohexane exhibited better processability coupled with lower melting points, lower cure onset with broad cure exotherm than the commercially available CE monomer, namely, 2,2-bis(4-cyanatophenyl) propane. Glass transition temperatures of cured 2,2-bis(4-cyanatophenyl) propane, 1,1-bis(4-cyanatophenyl) cyclohexane and 1,1-bis(4-cyanatophenyl) 3-pentadecylcyclohexane were observed to be 288 degrees C, 302 degrees C and 160 degrees C, respectively. Cured 1,1-bis(4-cyanatophenyl) cyclohexane displayed higher storage modulus (1.59 x 10(9) Pa) than 1,1-bis(4-cyanatophenyl) 3-pentadecylcyclohexane (1.07 x 10(9) Pa) and 2,2-bis(4-cyanatophenyl) propane (1.39 x 10(9) Pa). The order of thermal stability of cured polycyanurates was found to be 2,2-bis(4-cyanatophenyl) propane > 1,1-bis(4-cyanatophenyl) cyclohexane > 1,1-bis(4-cyanato phenyl) 3-pentadecylcyclohexane. The moisture absorption of cured resins derived from 1,1-bis(4-cyanatophenyl) 3-pentadecyl cyclohexane and 1,1-bis(4-cynatophenyl) cyclohexane was found to be lower than that of 2,2-bis(4-cynatophenyl) propane implying the role of pentadecyl substituent and/or cyclohexyl moiety in imparting hydrophobicity to the polycyanurates.

DOI10.1177/0954008312463738
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

1.09

Divison category: 
Polymer Science & Engineering