Citation: Khalil Faghihi, Mohsen Hajibeygi. OPTICALLY ACTIVE AND FLAME-RETARDANT POLY(AMIDE-IMIDE)S BASED ON PHOSPHINE OXIDE MOIETY AND N,N'-(PYROMELLITOYL)BIS-L-AMINO ACID IN THE MAIN CHAIN: SYNTHESIS AND CHARACTERIZATION[J]. Chinese Journal of Polymer Science, ;2010, 28(4): 517-525. doi: 10.1007/s10118-010-9075-0 shu

OPTICALLY ACTIVE AND FLAME-RETARDANT POLY(AMIDE-IMIDE)S BASED ON PHOSPHINE OXIDE MOIETY AND N,N'-(PYROMELLITOYL)BIS-L-AMINO ACID IN THE MAIN CHAIN: SYNTHESIS AND CHARACTERIZATION

Received Date: 12 May 2009
Revised Date: 28 June 2009

Six new optically active and flame-retardant poly(amide-imide)s PAIs 5a-5f containing phosphine oxide moiety as a flame-retardant unit in the main chain were synthesized from direct polycondensation reaction of six chiral N,N'-(pyromellitoyl)-bis-L-amino acid 3a-3f with bis(3-aminophenyl)phenyl phosphine oxide 4 in a medium consisting of N-methyl-2-pyrrolidone (NMP), triphenyl phosphite (TPP), calcium chloride (CaCl2) and pyridine. The polymerization reactions produced a series of optically active poly(amide-imide)s with good yield and good inherent viscosity of 0.34-0.70 dLg-1. The resulted polymers were fully characterized by means of FTIR and 1H-NMR spectroscopy, gel permeation chromatography (GPC), elemental analyses, inherent viscosity and solubility tests. Thermal properties and flame-retardant behavior of the PAIs 5a-5f were investigated using thermal gravimetric analysis (TGA and DTG) and limiting oxygen index (LOI). Data obtained by thermal analysis (TGA and DTG) revealed that these polymers showed good thermal stability. Furthermore, high char yield in TGA and good LOI values indicated that the resulting polymers were capable of exhibiting good flame retardant properties. N,N'-(pyromellitoyl)-bis-L-amino acids 3a-3f were prepared in quantitative yields by the condensation reaction of pyromellitic dianhydride (1,2,4,5-benzenetetracarboxylicacid-1,2,4,5-dianhydride) 1 with L-alanine 2a, L-valine 2b, L-leucine 2c, L-isoleucine 2d, L-phenyl alanine 2e and L-2-aminobutyric acid 2f in acetic acid solution.
1. [1]
  Xuan Song , Teng Fu , Yajie Yang , Yahan Kuang , Xiuli Wang , Yu-Zhong Wang . Spatial-confinement combustion strategy enabling free radicals chemiluminescence direct-measurement in flame-retardant mechanism. Chinese Chemical Letters, 2025, 36(5): 110699-. doi: 10.1016/j.cclet.2024.110699
2. [2]
  Qi Wei , Hua Xin , Xiaolong Wang , Changjuan Qin , Yuanzhen Su , Di Li , Jianxun Ding . Unimolecular chiral poly(amino acid)s as adjuvants of nanovaccines for augmented cancer immunotherapy. Chinese Chemical Letters, 2025, 36(11): 111477-. doi: 10.1016/j.cclet.2025.111477
3. [3]
  Tong Tong , Lezong Chen , Siying Wu , Zhong Cao , Yuanbin Song , Jun Wu . Establishment of a leucine-based poly(ester amide)s library with self-anticancer effect as nano-drug carrier for colorectal cancer treatment. Chinese Chemical Letters, 2024, 35(12): 109689-. doi: 10.1016/j.cclet.2024.109689
4. [4]
  Xing Cao , Xinyu Tian , Yuanyuan Huang , Liping Zhang , Yanpeng Ni , Yu-Zhong Wang . H₃PO₃-protonated chitosan enabling flame-retardant and antibacterial PVA composite films with high strength and toughness through multiple H-bonds and interlocking interfaces. Chinese Chemical Letters, 2025, 36(11): 111382-. doi: 10.1016/j.cclet.2025.111382
5. [5]
  Haojie Song , Laiyu Luo , Siyu Wang , Guo Zhang , Baojiang Jiang . Advances in poly(heptazine imide)/poly(triazine imide) photocatalyst. Chinese Chemical Letters, 2024, 35(10): 109347-. doi: 10.1016/j.cclet.2023.109347
6. [6]
  Xu He , Wenjie Gao , Jinglei Xu , Zhanjun Cheng , Wenchao Peng , Beibei Yan , Guanyi Chen , Ning Li . Machine learning-assisted construction of C=O and pyridinic N active sites in sludge-based catalysts. Chinese Chemical Letters, 2025, 36(12): 111019-. doi: 10.1016/j.cclet.2025.111019
7. [7]
  Qiang Luo , Jinfeng Sun , Zhibo Li , Bin Liu , Jianxun Ding . Thermo-sensitive poly(amino acid) hydrogel mediates cytoprotection through an antioxidant mechanism. Chinese Chemical Letters, 2025, 36(7): 110433-. doi: 10.1016/j.cclet.2024.110433
8. [8]
  Wanting CHEN , Chufei MIAO , Yan LIU , Bobi ZHENG , Xiaoyu ZHENG , Han XU , Jumei TIAN . Syntheses, characterization, and luminescence properties of Yb(Ⅲ)-based one-dimensional chain coordination polymer. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1672-1680. doi: 10.11862/CJIC.20250013
9. [9]
  Huihua GONG , Tianhua CUI , Li JI , Jichuan ZHANG , Liyuan ZHANG , Yan CHEN , Zhenye WANG , Jiaqi XU , Ruixiang LI . Hydrogenation of CO₂ to formate catalyzed by N-heterocyclic carbene-nitrogen-phosphine chelated iridium(Ⅰ) complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(12): 2609-2620. doi: 10.11862/CJIC.20250170
10. [10]
  Guoju Guo , Xufeng Li , Jie Ma , Yongjia Shi , Jian Lv , Daoshan Yang . Photocatalyst/metal-free sequential C–N/C–S bond formation: Synthesis of S-arylisothioureas via photoinduced EDA complex activation. Chinese Chemical Letters, 2024, 35(11): 110024-. doi: 10.1016/j.cclet.2024.110024
11. [11]
  Zhili Li , Qijun Wo , Dongdong Huang , Dezhong Zhou , Lei Guo , Yeqing Mao . Improving gene transfection efficiency of highly branched poly(β-amino ester)s through the in-situ conversion of inactive terminal groups. Chinese Chemical Letters, 2024, 35(8): 109737-. doi: 10.1016/j.cclet.2024.109737
12. [12]
  Hangwen Zheng , Ziqian Wang , HuiJie Zhang , Jing Lei , Rihui Li , Jian Yang , Haiyan Wang . Synthesis and applications of B, N co-doped carbons for zinc-based energy storage devices. Chinese Chemical Letters, 2025, 36(3): 110245-. doi: 10.1016/j.cclet.2024.110245
13. [13]
  Liping GUO . Synthesis and crystal structure characterization of yttrium imido complex: The reactivity of 2-substituted-1-amino-o-carborane with yttrium dialkyl complex. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1409-1415. doi: 10.11862/CJIC.20250065
14. [14]
  Long TANG , Yaxin BIAN , Luyuan CHEN , Xiangyang HOU , Xiao WANG , Jijiang WANG . Syntheses, structures, and properties of three coordination polymers based on 5-ethylpyridine-2,3-dicarboxylic acid and N-containing ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1975-1985. doi: 10.11862/CJIC.20240180
15. [15]
  Menglin Zhou , Lin Zhang , Xuefei Shan , Fengqin Chang , Wentong Chen , Xuguang An , Guangzhi Hu . Hydrangea-like B/N co-doped carbon-based electrochemical sensors for the efficient and sensitive detection of aristolochic acid in Aristolochia. Chinese Chemical Letters, 2025, 36(12): 111073-. doi: 10.1016/j.cclet.2025.111073
16. [16]
  Ming-Ming Gan , Zi-En Zhang , Xin Li , F. Ekkehardt Hahn , Ying-Feng Han . Hierarchical self-assembly of fluorinated poly-N-heterocyclic carbene pillarplexes with anions. Chinese Chemical Letters, 2025, 36(10): 110624-. doi: 10.1016/j.cclet.2024.110624
17. [17]
  Haibo Ye , Qianyu Li , Juan Li , Didi Li , Zhimin Ao . Review on the abiotic degradation of biodegradable plastic poly(butylene adipate-terephthalate): Mechanisms and main factors of the degradation. Chinese Chemical Letters, 2025, 36(1): 109861-. doi: 10.1016/j.cclet.2024.109861
18. [18]
  Chaochao Jin , Kai Li , Jiongpei Zhang , Zhihua Wang , Jiajing Tan . N,O-Bidentated difluoroboron complexes based on pyridine-ester enolates: Facile synthesis, post-complexation modification, optical properties, and applications. Chinese Chemical Letters, 2024, 35(9): 109532-. doi: 10.1016/j.cclet.2024.109532
19. [19]
  Yun-Xin Huang , Lin-Qian Yu , Ke-Yu Chen , Hao Wang , Shou-Yan Zhao , Bao-Cheng Huang , Ren-Cun Jin . Biochar with self-doped N to activate peroxymonosulfate for bisphenol-A degradation via electron transfer mechanism: The active edge graphitic N site. Chinese Chemical Letters, 2024, 35(9): 109437-. doi: 10.1016/j.cclet.2023.109437
20. [20]
  Jiarong ZHU , Xiaohua ZHANG , Xinting XIONG , Xuliang NIE , Xiuying SONG , Miaomiao ZHANG , Dayong PENG , Xiuguang YI . Crystal structure, Hirshfeld surface analysis, and antifungal activity of five complexes based on 2,5-bis(carboxymethoxy)terephthalic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(11): 2358-2370. doi: 10.11862/CJIC.20250150

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(1199)
HTML views(57)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

Address：Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888

DownLoad: Full-Size Img PowerPoint

Return