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Synthesis and properties of novel fluorinated polyamides based on noncoplanar sulfoxide containing aromatic bis(ether amine)

Shockravi, A ; Sharif University of Technology | 2009

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  1. Type of Document: Article
  2. DOI: 10.1295/polymj.PJ2008250
  3. Publisher: 2009
  4. Abstract:
  5. A novel sulfoxide containing bis(ether amine) monomer, 2,2'-sulfoxide- bis[4-methyl(2-trifluoromethyl)4-aminophenoxy) phenyl ether] (M2), was synthesized from the halogen displacement of 2-chloro-5-nitrobenzotrifluoride with dibenzosulfoxide (DH) in the presence of potassium carbonate, followed by catalytic reduction of bis(ether nitro) intermediate with Zinc/Ammonium chloride. A series of organic-soluble poly(ether amide)s (PA1-7) bearing sulfoxide and electronwithdrawing trifiuoromethyl group were synthesized from bis(ether amine) with various aromatic diacids (1-7) via a direct polycondensation with triphenyl phosphite and pyridine. The resulting polymers had inherent viscosities ranging from 0.35 to 0.90 dLg-1 at a concentration of 0.5 g/dL in N,N-dimethylacetamide (DMAc) solvent at 25 °C. All the polymers showed outstanding solubility and could be easily dissolved in amide-type polar aprotic solvents (e.g., N-methyl-2-pyrrolidone (NMP), DMAc, and N.N-dimethylformamide) and even dissolved in less polar solvents (e.g., pyridine, and tetrahydrofuran). Also these polymers could be cast into flexible and tough films from DMAc solutions. The glass-transition temperatures of these poly(sulfoxide ether amide)s were recorded between 160-220 °C. 10% weight loss temperatures were recorded in the range of 400-505 °C in nitrogen and 380-480 °C in air atmosphere. ©2009 The Society of Polymer Science, Japan
  6. Keywords:
  7. Fluorinated polyamides ; Improved solubility ; Air atmosphere ; Catalytic reduction ; Concentration of ; Direct polycondensation ; Electronwithdrawing ; Fluorinated polyamides ; Glass transition temperature ; Halogen displacement ; Inherent viscosity ; N ,N-Dimethylacetamide ; N-methyl-2-pyrrolidone ; Non-coplanar ; Phenyl ethers ; Polar aprotic solvent ; Polar solvents ; Poly(sulfoxide-ether-amide)s ; Potassium carbonates ; Sulfoxide containing polyamide ; Tetra-hydrofuran ; Thermal stability ; Trifluoromethyl ; Triphenyl phosphite ; Weight loss temperatures ; Amides ; Amines ; Amino acids ; Aromatic compounds ; Chlorine compounds ; Dimethylformamide ; Dissolution ; Glass transition ; Ionic liquids ; Nylon polymers ; Polycondensation ; Polymers ; Potash ; Potassium ; Pyridine ; Solubility ; Solvents ; Synthesis (chemical) ; Ternary systems ; Thermodynamic stability ; Ethers
  8. Source: Polymer Journal ; Volume 41, Issue 3 , 2009 , Pages 174-180 ; 00323896 (ISSN)
  9. URL: https://www.nature.com/articles/pj200930