Ebrahim Abouzari-Lotf - Fluorinated ortho-linked polyamides derived from non-coplanar 1,1′-thiobis(2-naphthol): Synthesis and characterization

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      Shockravi, A., Javadi, A., Abouzari-Lotf, E. 43 (10)   816-825

      Abstract: A novel sulfide-bridged bis(ether   amine) monomer containing bulky trifluoromethyl and naphthyl   substituents, 1,1′-thiobis2-(4-amino-2-   trifluoromethylphenoxy)naphthalene, was synthesized from the   halogen displacement of 2-chloro-5-nitrobenzotrifluoride with   1,1′-thiobis(2- naphthol) in the presence of potassium carbonate,   followed by the palladium on activated carbon-catalyzed reduction   of bis(ether nitro) intermediate,   1,1′-thiobis2-(4-nitro-2-trifluoromethylphenoxy)naphthalene, with   hydrazine hydrate in refluxing ethanol. New series of fluorinated   poly(ether amide)s (PEA-1-8) were synthesized from bis(ether   amine) with various commercially available aromatic diacids (1-8)   via a direct polycondensation method with triphenyl phosphite and   pyridine. The resulting polymers had inherent viscosities,   ranging from 0.61 to 0.93 dl g-1. All the polymers showed   outstanding solubility and could be easily dissolved in   amide-type polar aprotic solvents (for example,   N-methyl-2-pyrrolidone, dimethyl sulfoxide and   N,N-dimethylacetamide (DMAc)), and even dissolved in less polar   solvents (for example, pyridine, tetrahydrofuran and chloroform).   In addition, these polymers could be cast into transparent,   flexible and tough films from DMAc solutions. The   glass-transition temperatures were recorded between 209 and   251°C, and 10% weight loss temperatures were in excess of 470 °C   in nitrogen and 450 °C in air atmosphere. Moreover, these PEAs   exhibited low refractive indices (n=1.5614-1.5813), birefringence   (Δ=0.0055-0.0097) and dielectric constants (ε=2.68-2.75). © The   Society of Polymer Science, Japan (SPSJ) All rights reserved.

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