화학공학소재연구정보센터
Polymer Bulletin, Vol.44, No.3, 277-284, 2000
Steric effect in the free radical polymerization of vinyl ethers containing electron-deficient olefin groups
o-(2-vinyloxyethoxy)benzylidenemalononitrile (3a), methyl o-(2-vinyloxyethoxy)benzylidenecyanoacetate (3b), 1,3-di-(2'-dicyanovinyl)-5-methyl-2-(2'-vinyloxyethoxy) benzene (4a), methyl 1,3 -di-(2'-carbomethoxy-2'-cyanovinyl)-5-methyl-2-(2'-vinyloxyethoxy)benzene (4b), 2,3,4-tri-(2'-vinyloxyethoxy)benzylidenemarononitrile (5a), methyl 2,3,4-tri-(2'-vinyloxyethoxy)benzylidenecyanoacetate (5b), 2,4,6-tri-(2'-vinyl oxyethoxy)benzylidenemalononitrile (6a), and methyl 2,4,6-tri-(2'-vinyloxyethoxy)ben zylidenecyanoacetate (6b) were prepared by the condensation of o-(2-vinyloxyethoxy) benzaldehyde (1a), 2-(2'-vinyloxyethoxy)-5-methylisophthaldehyde (1b), 2,3,4-tri-(2'-vinyloxyethoxy)benzaldehyde (2a), 2,4,6-tri-(2'-vinyloxyethoxy)benzaldehyde (2b) with malononitrile or methyl cyanoacetate, respectively. Vinyl ether compounds 3a-b and 5a-b were polymerized readily by free radical initiators to give optically transparent swelling poly(vinyl ethers) 7a-b and 9a-b. Compounds 4a-b and 6a-b did not polymerize by radical initiators due to the steric hindrance. Polymers 7a-b and 9a-b were not soluble in common organic solvents such as acetone and DMSO due to crosslinking. Polymers 7a-b and 9a-b showed a thermal stability up to 300 degrees C in TGA thermograms.