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Polyimides from 1,5-bis(4-amino-2-trifluoromethylphenoxy)naphthalene and aromatic tetracarboxylic dianhydrides
Authors:Sheng-Huei Hsiao  Chin-Ping Yang  Sheng-Ching Huang
Institution:Department of Chemical Engineering, Tatung University, 40 Chungshan North Road, Section 3, Taipei 104, Taiwan, ROC
Abstract:A new trifluoromethylated bis(ether amine), 1,5-bis(4-amino-2-trifluoromethylphenoxy)naphthalene, was synthesized in two steps starting from 1,5-dihydroxynaphthalene and 2-chloro-5-nitrobenzotrifluoride via nucleophilic aromatic substitution and catalytic reduction. A series of novel fluorinated polyimides with moderate to high molecular weights were synthesized from the diamine with various aromatic tetracarboxylic dianhydrides using a conventional two-stage process. All polyimides could afford flexible and tough films and most of them were soluble in strong polar solvents such as N-methyl-2-pyrrolidone (NMP) and N,N-dimethylacetamide (DMAc). The polyimides showed glass-transition temperatures (Tg) in the range of 253-315 °C (by DSC) and softening temperatures (Ts) in the range of 250-300 °C (by TMA). Decomposition temperatures for 5% weight loss all occurred above 500 °C in both air and nitrogen atmospheres. The dielectric constants of these polymers ranged from 3.17 to 3.64 at 1 MHz. The properties of these fluorinated polyimides were also compared with those of polyimides prepared from 1,5-bis(4-aminophenoxy)naphthalene with the same dianhydrides.
Keywords:Fluorine-containing polyimides  Trifluoromethyl  High solubility
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