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Synthesis and characterization of soluble and heat-resistant aromatic polyamides derived from diamine; N-(3,5-diaminophenyl)-4-(naphthalen-7-yloxy)benzamide and various aromatic diacids
Journal of Macromolecular Science, Part A ( IF 2.5 ) Pub Date : 2021-06-01 , DOI: 10.1080/10601325.2021.1922084
Shivaji. D. Ghodke 1 , Aslam B. Tamboli 2 , Arati V. Diwate 3 , Mahesh B. Gurame 4 , Vijay P. Ubale 5 , Rajesh G. Bhorkade 4 , Noormahmad N. Maldar 4
Affiliation  

Abstract

The new aromatic m-catenated diamine, N-(3,5-diaminophenyl)-4-(naphthalen-7-yloxy)benzamide was synthesized from 2-naphthol and 4-fluoro benzonitrile as starting materials. A series of novel aromatic polyamides were synthesized from the diamine and several aromatic diacids such as 4,4′-Oxydibenzoic acid, Naphthalene-2, 6-dicarboxylic acid, 4,4′-Sulfonyldibenzoic acid, Biphenyl-4,4′-dicarboxylic acid and 4,4′-(perfluoropropane-2, 2-diyl) dibenzoic acid via direct Yamazaki’s phosphorylative polycondensation method with triphenyl phosphite (TPP) as a condensing agent in pyridine (Py)/LiCl/1-methyl-2-pyrrolidone (NMP) solvent system. These new m-catenated/kink structured polyamides containing pendant naphthalene-oxy-benzamide units, were characterized by inherent viscosities, solubility in organic solvents, FTIR, DSC, TGA and XRD techniques. The polyamides were obtained in good yields and had inherent viscosities in range 0.35 and 0.55 dL/g. These polyamides were soluble in amide type aprotic solvents namely N, N′ dimethyl formamide (DMF), N-methyl-2-pyrrolidone (NMP), N, N′ dimethyl acetamide (DMAc), dimethyl sulfoxide (DMSO) and partly soluble in m-cresol, tetrahydrofuran (THF) and chloroform or dichloromethane. Polyamides showed glass-transition temperatures in the range 224 °C–262 °C indicating their processability at these temperatures. Thermogravimetric analysis in nitrogen atmosphere showed the 10% weight loss temperatures were more than 555 °C, indicating a good thermal stability. X-ray diffraction patterns of these polyamides indicated the amorphous nature, which is reflected in solubility characteristics.



中文翻译:

二胺衍生的可溶性耐热芳香族聚酰胺的合成与表征;N-(3,5-二氨基苯基)-4-(naphthalen-7-yloxy)benzamide 和各种芳香族二酸

摘要

以2-萘酚和4-氟苄腈为原料合成了新型芳香间链二胺N-(3,5-二氨基苯基)-4-(naphthalen-7-yloxy)benzamide。以二胺和4,4'-氧二苯甲酸、Naphthalene-2, 6-二甲酸、4,4'-磺酰二苯甲酸、联苯-4,4'-二甲酸等芳香族二元酸为原料合成了一系列新型芳香族聚酰胺。在吡啶 (Py)/LiCl/1-甲基-2-吡咯烷酮中,以亚磷酸三苯酯 (TPP) 为缩合剂,通过山崎直接的磷酸化缩聚反应合成酸和 4,4'-(全氟丙烷-2, 2-二基)二苯甲酸 ( NMP) 溶剂系统。这些含有侧链萘-氧-苯甲酰胺单元的新型间链/扭结结构聚酰胺通过固有粘度、在有机溶剂中的溶解度、FTIR、DSC、TGA 和 XRD 技术进行表征。聚酰胺以良好的收率获得并且具有在0.35和0.55dL/g范围内的特性粘度。这些聚酰胺可溶于酰胺类非质子溶剂,即 N, N' 二甲基甲酰胺 (DMF)、N-甲基-2-吡咯烷酮 (NMP)、N, N' 二甲基乙酰胺 (DMAc)、二甲亚砜 (DMSO) 并部分溶于间甲酚、四氢呋喃 (THF) 和氯仿或二氯甲烷。聚酰胺的玻璃化转变温度范围为 224 °C–262 °C,表明它们在这些温度下具有可加工性。氮气氛下热重分析表明10%失重温度超过555℃,表明具有良好的热稳定性。这些聚酰胺的 X 射线衍射图表明无定形性质,这反映在溶解度特征中。

更新日期:2021-06-01
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