Rigid-Rod Polyamides from 3,3 '-bis-(trifluoromethyl)-4,4 '-diamino-1,1 '-biphenyl

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A diamine monomer with trifluoromethyl groups, 3,3'-bis#trifluoromethyl#-4,4'-diamino-1,1'-biphenyl, is synthesized from 5-bromo-2-nitrobenzotrifluoride with two steps. The model reaction with monofunctional benzoyl chloride at room temperature gives the model compound with a quantitative yield. The results of the model reaction indicate that the amine groups have sufficient reactivity in spite of the presence of electron-withdrawing and bulky trifluoromethyl group at the ortho position. The monomer is polymerized with terephthaloyl chloride and isophthaloyl chloride in N,N-dimethylacetamide #DMAc# or DMAc containing LiCl using pyridine as an acid acceptor at room temperature. All synthesized polymers are somewhat crystalline and colorless. While the meta-linked polyamide #PA2# shows excellent solubility in polar aprotic solvents, the para-linked one #PA1# is dissolved in polar aprotic solvents containing LiCl and concentrated H2SO4. They show good thermal and thermooxidative stability as well as high melting temperatures.
Publisher
WILEY-V C H VERLAG GMBH
Issue Date
2015-06
Language
English
Article Type
Article
Keywords

TRIFLUOROMETHYL PENDENT GROUPS; NITRO DISPLACEMENT REACTION; AROMATIC POLYAMIDES; SOLUBLE POLYIMIDES; POLY(BIPHENYLENE OXIDE)S; UNSYMMETRICAL DIAMINE; POLY(ARYLENE ETHER)S; POLYMERS

Citation

MACROMOLECULAR CHEMISTRY AND PHYSICS, v.216, no.12, pp.1341 - 1347

ISSN
1022-1352
DOI
10.1002/macp.201500013
URI
http://hdl.handle.net/10203/200068
Appears in Collection
CH-Journal Papers(저널논문)
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