Synthesis and Properties of Organo-soluble Polyamides Derived from 2,2’-Diiodo-4,4’-oxydianiline、2,8-Diaminodibenzofuran and 2,2’-Bis[p-(trifluoromethyl)phenyl]-4,4’-oxydianiline

• Main Authors: HUANG, SHENG-WEN, 黃聖文
• Other Authors: Jyh-Chien Chen
• Format: Others
• Language: zh-TW
• Published: 2010
• Online Access: http://ndltd.ncl.edu.tw/handle/50507759134542888378

碩士 === 國立臺灣科技大學 === 高分子系 === 98 === Three aromatic diamines 2,2’-diiodo-4,4’-oxydianiline (DI-ODA 3), 2,8-diamino dibenzofuran (DADBF 5) and 2,2’-[bis(p-trifluoromethyl)phenyl]-4,4’-oxidianiline (BP-ODA 7) were synthesized by using 4,4’-oxydianiline (4,4’-ODA) as a starting material. Novel polyamides PA8a~f, PA9a~f, PA10a~f were prepared by the direct polycondensation of three diamines with various commercially available aromatic dicarboxylic acids. Inherent viscosities of the polyamides were in the range of 0.27-0.89 dL/g in N-methyl-2-pyrrolidinone (NMP) or concentrated sulfuric acid at 30 oC. The introduction of ether linkages and pendant groups (iodine and p-trifluoromethyphenyl) into polyamides led to an enhanced solubility in organic solvents such as N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMAc), N,N-dimethylsulfoxide (DMSO) and NMP at room temperature or upon heating. Especially, polyamides 8a, 8b, 10a and 10b containing rigid p-phenylene and m-phenylene structures can be soluble in DMF, DMAc, DMSO, NMP and m-cresol at room temperature. The polyamides could be solution-cast into transparent films from their N,N-dimethylacetamide solution. These films had the UV onset wavelengths in the range of 333-381 nm and wave-lengths at 80% transmission of 379-578 nm, indicating high optical transparency. Wide angle X-ray diffraction patterns indicated that the polymers were essentially amorphous in nature. The glass transition temperature observed for the polyamides were in the range of 243-354 oC. The temperature at 5% weight loss (Td5%), determined by TGA in nitrogen atmosphere, were in the range of 350-533 oC, indicating their good thermal stability. Due to the weak carbon-iodine bond, polyamide 8 containing iodine substituents decomposed at lower temperatures then polyamides 9 and 10. High optical transparency combined with excellent solubility and high thermal stability makes these polyamides potential candidates for soft electronic applications.