Hydrazine‐based polyimides from isomeric bis(chlorophthalimide)s |
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| Authors: | Jingling Yan Taihang Li Zhen Wang Lianxun Gao Mengxian Ding |
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| Affiliation: | 1. State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, People's Republic of China;2. Graduate University of Chinese Academy of Sciences, Beijing 100049, People's Republic of China;3. Department of Organic Chemistry, School of Biological Engineering, Changchun University of Technology, Changchun 130012, People's Republic of China;4. State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, People's Republic of ChinaState Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, People's Republic of China |
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| Abstract: | 3,3′‐Dichloro‐N,N′‐biphthalimide (3,3′‐DCBPI), 3,4′‐dichloro‐N,N′‐biphthalimide (3,4′‐DCBPI), and 4,4′‐dichloro‐N,N′‐biphthalimide (4,4′‐DCBPI) were synthesized from 3‐ or 4‐chlorophthalic anhydrides and hydrazine in glacial acetic acid. The yield of 3,3′‐DCBPI (90%) was much higher than that of 4,4′‐DCBPI (33%) because of the better stability of the intermediate, 3‐chloro‐N‐aminophthalimide, and 3,3′‐DCBPI. A series of hydrazine‐based polyimides were prepared from isomeric DCBPIs and 4,4′‐thiobisbenzenethiol (TBBT) in N,N‐dimethylacetamide in the presence of tributylamine. Inherent viscosity of these polymers was in the range of 0.51–0.69 dL/g in 1‐methyl‐2‐pyrrolidinone (NMP) at 30 °C. These polyimides were soluble in 1,1,2,2‐terachloroethane, NMP, and phenols. The 5% weight‐loss temperatures (T5%s) of the polymers were near 450 °C in N2. Their glass‐transition temperatures (Tgs) determined by dynamic mechanical thermal analysis and differential scanning calorimetry increased according to the order of polyimides based on 4,4′‐DCBPI, 3,4′‐DCBPI, and 3,3′‐DCBPI. The hydrolytic stability of these polymers was measured under acid, basic, and neutral conditions and the results indicated that the order was 3,3′‐DCBPI/TBBT > 3,4′‐DCBPI/TBBT > 4,4′‐DCBPI/TBBT. © 2007 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 45: 4933–4940, 2007 |
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| Keywords: | dichloro‐N,N′ ‐biphthalimides hydrazine‐based polyimides isomer effect polyimides structure– property relations synthesis |
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