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High Performance Soluble Polyimides from Ladder-Type Fluorinated Dianhydride with Polymorphism.

ABSTRACT: A novel rigid semi-alicyclic dianhydride 9,10-difluoro-9,10-bis(trifluoromethyl)-9,10-dihydroanthracene-2,3,6,7-tetracarboxylic acid dianhydride (8FDA) was reported, and its single crystal X-ray diffraction result revealed the existence of the polymorphic structure in this compound. The detail geometric configuration transition during the synthesized process was investigated, exhibiting a transition of from trans- to cis- when the hydroxyl groups were substituted by fluoride with diethylaminosulfur trifluoride (DAST). Compared with the dianhydride 4,4'-(Hexaflouroisopropylidene) diphthalic anhydride (6FDA) and 1S,2R,4S,5R-cyclohexanetetracarboxylic dianhydride (HPMDA), the resulting polyimide (PI) films based on 8FDA exhibited an obviously higher glass transition temperature (T_g, 401 °C) and a much lower coefficient of thermal expansion (CTE, 14 ppm K^-1). This indicates that 8FDA is an ideal building block in high-performance soluble PIs with low CTE.

SUBMITTER: Li F

PROVIDER: S-EPMC6415444 | biostudies-literature | 2018 May

REPOSITORIES: biostudies-literature

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High Performance Soluble Polyimides from Ladder-Type Fluorinated Dianhydride with Polymorphism.

Li Fu F Liu Jikang J Liu Xiangfu X Wang Yao Y Gao Xiang X Meng Xianggao X Tu Guoli G

Polymers 20180518 5

A novel rigid semi-alicyclic dianhydride 9,10-difluoro-9,10-bis(trifluoromethyl)-9,10-dihydroanthracene-2,3,6,7-tetracarboxylic acid dianhydride (8FDA) was reported, and its single crystal X-ray diffraction result revealed the existence of the polymorphic structure in this compound. The detail geometric configuration transition during the synthesized process was investigated, exhibiting a transition of from <i>trans</i>- to <i>cis</i>- when the hydroxyl groups were substituted by fluoride with d ...[more]

PMID: 30966580

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Project description:In this work we report the effect of the hard block dianhydride structure on the overall properties of partially biobased semiaromatic polyimides. For the study, four polyimides were synthesized using aliphatic fatty dimer diamine (DD1) as the soft block and four different commercially available aromatic dianhydrides as the hard block: 4,4'-(4,4'-isopropylidenediphenoxy) bis(phthalic anhydride) (BPADA), 4,4'-oxidiphthalic anhydride (ODPA), 4,4'-(Hexafluoroisopropylidene) diphthalic anhydride (6FDA), and 3,3',4,4'-biphenyltetracarboxylic dianhydride (BPDA). The polymers synthesized were fully organo-soluble thermoplastic branched polyimides with glass transition temperatures close to room temperature. The detailed analysis took into account several aspects of the dianhydrides structure (planarity, rigidity, bridging group between the phtalimides, and electronic properties) and related them to the results obtained by differential scanning calorimetry, rheology, fluorescence and broadband dielectric spectroscopy. Moreover, the effects of physical parameters (crystallization and electronic interactions) on the relaxation behavior are discussed. Despite the presence of the bulky branched soft block given by the dimer diamine, all polyimides showed intermolecular charge transfer complexes, whose extent depends on the electronic properties of the dianhydride hard block. Furthermore, the results showed that polyimides containing flexible and bulky hard blocks turned out fully amorphous while the more rigid dianhydride (BPDA) led to a nanophase separated morphology with low degree of crystallinity resulting in constrained segmental relaxation with high effect on its mechanical response with the annealing time. This work represents the first detailed report on the development and characterization of polyimides based on a biobased fatty dimer diamine. The results highlight the potential of polymer property design by controlled engineering of the aromatic dianhydride blocks.

Dataset Information

High Performance Soluble Polyimides from Ladder-Type Fluorinated Dianhydride with Polymorphism.

Publications

High Performance Soluble Polyimides from Ladder-Type Fluorinated Dianhydride with Polymorphism.

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