Steric effect in the free radical polymerization of vinyl ethers containing electron-deficient olefin groups

Summaryo-(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...

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Bibliographic Details
Published in:Polymer bulletin (Berlin, Germany) Germany), 2000-04, Vol.44 (3), p.277-284
Main Authors: LEE, J.-Y, JIN, M.-K
Format: Article
Language:English
Subjects:
Applied sciences
Benzaldehyde
Benzene
Crosslinking
Exact sciences and technology
Free radical polymerization
Free radicals
Initiators
Malononitrile
Organic polymers
Physicochemistry of polymers
Polymers
Polymers with particular properties
Polyvinyl ethers
Preparation, kinetics, thermodynamics, mechanism and catalysts
Steric hindrance
Thermal stability
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Summary:Summaryo-(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)benzylidenemalononitrile (5a), methyl 2,3,4-tri-(2'-vinyloxyethoxy)benzylidenecyanoacetate (5b), 2,4,6-tri-(2'-vinyloxyethoxy)benzylidenemalononitrile (6a), and methyl 2,4,6-tri-(2'-vinyloxyethoxy)benzylidenecyanoacetate (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°C in TGA thermograms.
ISSN:0170-0839
1436-2449
DOI:10.1007/s002890050603