Synthesis and properties of novel polyurethanes containing 2,4-dioxybenzylidenecyanoacetate group as a NLO-chromophore for electro-optic applications

SummaryMethyl 2,4-bis-(2'-hydroxyethoxy)benzylidenecyanoacetate (3) was prepared by hydrolysis of methyl 2,4-bis-(2'-vinyloxyethoxy)benzylidenecyanoacetate (2). Diol 3 was condensed with 2,4-toluenediisocyanate, 3,3'-dimethoxy-4,4'-biphenylene-diisocyanate, and 1,6-hexamethylened...

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Bibliographic Details
Published in:Polymer bulletin (Berlin, Germany) Germany), 2002-05, Vol.48 (3), p.233-241
Main Authors: LEES, Ju-Yeon, PARK, Eun-Ju, HOOSUNG LEE, BUM KU RHEE
Format: Article
Language:English
Subjects:
Applied sciences
Chromophores
Diisocyanates
Exact sciences and technology
Organic polymers
Physicochemistry of polymers
Polymer films
Polymers with particular properties
Polyurethane
Preparation, kinetics, thermodynamics, mechanism and catalysts
Thermal stability
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Summary:SummaryMethyl 2,4-bis-(2'-hydroxyethoxy)benzylidenecyanoacetate (3) was prepared by hydrolysis of methyl 2,4-bis-(2'-vinyloxyethoxy)benzylidenecyanoacetate (2). Diol 3 was condensed with 2,4-toluenediisocyanate, 3,3'-dimethoxy-4,4'-biphenylene-diisocyanate, and 1,6-hexamethylenediisocyanate to yield polyurethanes 4–6 containing the NLO-chromophore 2,4-dioxybenzylidenecyanoacetate. The resulting polyurethanes 4–6 were soluble in common organic solvents such as acetone and DMF. Polymers 4–6 showed a thermal stability up to 280°C in TGA thermograms with Tg values obtained from DSC thermograms in the range of 66–114°C. The SHG coefficients (d33) of poled polymer films were around 7.8 × 10−9 esu.
ISSN:0170-0839
1436-2449
DOI:10.1007/s00289-002-0040-0