Synthesis, Characterization and Property of Poly(aryl ether amides) from 2-(4-Aminophenyl)-4-(3-methyl-4-aminophenoxy)-2,3-phthalazinone

Abstract

Abstract: A novel aromatic diamine 2-(4-aminophenyl)-4-(3-methyl-4-aminophenoxy)-2,3-phthalazinone-1(1, DAMPP) containing aza heterocycle was synthesized in a higher yield starting from 4-(3-methyl-4-hydroxyphenyl)-2,3-phthalazinone-1(OM-HPPZ) via two steps conveniently. Diamine 1 polymerized with three aryl dicarboxylic acids to prepare a series of new aromatic polyamides in a high yield using Yamazaki phosphorylation method. The synthesized polymer has a high molecular weight with the inherent viscosity in the range of 0.40-0.60 dL/g. They exhibited high glass transition temperatures of 598-620 K and good thermostable properties with the 10% weight loss temperature above 673 K(in nitrogen). The range of their surface resistance coefficients is 5.89×10¹⁵-9.87×10¹⁵ Ω and the range of volume resistance coefficients is 1.39×10¹⁶-4.09×10¹⁶ Ω·cm. These polymers were readily soluble in polar solvents such as NMP, DMF and m-cresol etc, clear tough films were cast from their DMAc solutions. The structures of diamine 1 and polymers obtained was confirmed by MS, FTIR and ¹HNMR, which are consistent with the designed structure.

Key words: Poly(aryl amide), Heterocyclic polymer, Phthalazinone, Solubility

CLC Number:

TQ324.8

TrendMD:

ZHU Xiu-Ling, JIAN Xi-Gao, LU Ye, WANG Rui-Ling, ZHANG Yuan-Hong . Synthesis, Characterization and Property of Poly(aryl ether amides) from 2-(4-Aminophenyl)-4-(3-methyl-4-aminophenoxy)-2,3-phthalazinone[J]. Chem. J. Chinese Universities, 2003, 24(2): 355.

[1]	WANG Shoubai, WU Xiuming, WU Jinming, TANG Yanfeng, SHU Chen, ZHONG Min, HUANG Wei, YAN Deyue. Synthesis and Properties of Soluble Transparent Polyimides Containing tert-Butyl and Isobutyl Groups [J]. Chem. J. Chinese Universities, 2021, 42(9): 2944.
[2]	FU Zhinan, TAN Yunlong, XIAO Guyu, YAN Deyue. Synthesis and Properties of Sulfonated Poly（phthalazinone ether phosphine oxide）s with Perfluorobiphenyl Moieties for Proton Exchange Membranes [J]. Chem. J. Chinese Universities, 2021, 42(8): 2635.
[3]	WANG Xianwei, KE Hongjun, YUAN Hang, LU Gewu, LI Liying, MENG Xiangsheng, SONG Shulin, WANG Zhen. High Temperature Resistant and Soluble Polyimide Resins and Their Composites [J]. Chem. J. Chinese Universities, 2021, 42(6): 2041.
[4]	ZHANG Danwei, WANG Hui, LI Zhanting. Water-soluble Regular Three-dimensional Supramolecular and Covalent Organic Polymers ^† [J]. Chem. J. Chinese Universities, 2020, 41(6): 1139.
[5]	JIANG Jing,HUANG Yali,ZHANG Qilong,XU Hong,SUN Xiaohong. Effects of Cucurbit[8]uril on the Solubility, Stability and Antioxidation of Cyanidin^† [J]. Chem. J. Chinese Universities, 2019, 40(1): 76.
[6]	YU Kaile,PAN Xinyu,ZHANG Zhengfang,WANG Qiang. Determination of Solubility Parameters of Imidazolyl Acetate Ionic Liquid by Inverse Gas Chromatography and Hansen Solubility Parameters^† [J]. Chem. J. Chinese Universities, 2018, 39(5): 1048.
[7]	YANG Tong, PENG Rong, HUANG Xinyu, SUN Yansong, CHEN Xiaonong. Relative Hydrophobicity of Drug Molecules and Retention Behavior in Hydrophobic Interaction Chromatography^† [J]. Chem. J. Chinese Universities, 2018, 39(11): 2405.
[8]	ZHANG Hanyu, LUO Wu, LIU Zhenchao, LI Xiaobai, Guan Shaowei, LIU Baijun. Preparation of the Biphenyl-containing Polyarylethers with Highly Fluorinated Contents [J]. Chem. J. Chinese Universities, 2017, 38(7): 1107.
[9]	WANG Luyuan, LIU Shuxue, LI Huimin, HUANG Yaodong. Preparation and Properties of the Two-component Hydrogels Based on Pyrazine Dicarboxylic Acid and Melamine^† [J]. Chem. J. Chinese Universities, 2017, 38(5): 806.
[10]	QIU Chuanlong,LI Chunfang,LI Dongxiang,HOU Wanguo. Synthesis, Characterization and Aggregation Behavior of Polyethylene Glycol-conjugated Hydroxycamptothecin^† [J]. Chem. J. Chinese Universities, 2016, 37(8): 1535.
[11]	WANG Xiao, YANG Xinguo, SHEN Qili. Synthesis and Gel Properties of a Novel Amide Gelator with Melamine Moieties and Rationalizing Gelation Behavior by Hansen Solubility Parameters^† [J]. Chem. J. Chinese Universities, 2016, 37(11): 2068.
[12]	FAN Weifeng, LIU Xiuju, YAN Jingling, MENG Xiangsheng, LIU Jingfeng, WANG Zhen. Thermosetting Polyimide Resins and Composites Derived from 2-Phenyl-4,4'-oxydianiline^† [J]. Chem. J. Chinese Universities, 2016, 37(10): 1926.
[13]	WANG Bin, LUO Haiyan, ZHANG Yonghong, SUN Yadong, LIU Chenjiang. Synthesis and Properties of Chiral Ionic Liquid Based on (R)-Thiazolidine-2-thione-4-carboxylate^† [J]. Chem. J. Chinese Universities, 2015, 36(8): 1530.
[14]	JIANG Guangce, LIN Xiongchao, ZHANG Shengjuan, WANG Zhongqi, WANG Yonggang, CHEN Qiang, ZHU Yufei. Supercritical Fluid Extraction of Direct Coal Liquefaction Residue Basing on Hansen Solubility Parameters^† [J]. Chem. J. Chinese Universities, 2015, 36(3): 544.
[15]	HE Rui, WANG Xiaona, WANG Xinyue, QIU Ya, YANG Shengyong, YIN Zongning. Insight into the Formation Mechanisms Behind Self-emulsifying Drug Delivery Systems of Calcium Channel Blockers^† [J]. Chem. J. Chinese Universities, 2015, 36(1): 131.

Synthesis, Characterization and Property of Poly(aryl ether amides) from 2-(4-Aminophenyl)-4-(3-methyl-4-aminophenoxy)-2,3-phthalazinone

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments