Synthesis and properties of organosoluble polyimides based on novel perfluorinated monomer hexafluoro-2,4-toluenediamine

Shundrina, Inna K.; Vaganova, T. A.; Kusov, Soltan Z.; Rodionov, Vladimir; Карпова, Е. В.; Malykhin, E. V.

doi:10.1016/j.jfluchem.2011.01.008

Cited by 31 publications

(14 citation statements)

References 41 publications

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“…However, PI with the wholly aromatic structure has poor solubility and non‐melting property attributed to its rigid main chain and strong inter‐chain interaction, which limit its practical applications seriously. Fortunately, researchers have mainly concluded four aspects of structure modification by enhancing the flexibility of molecular main chain and weakening the intermolecular interaction of PI in order to improve its solubility in the past decades, which involved the incorporation of thermally stable but flexible linkages in the main chain, the synthesis of unsymmetrical linkages in the main chain, the introduction of polar or nonpolar substituent branched to the main chain, and the destruction of symmetrical structure of the main chain with the introduction of hyperbranched structure . In particular, the researchers have found that the incorporation of aromatic heterocyclic compounds into the main chain could form thermally stable and flexible linkages in PIs main chain, which would reduce the intermolecular interaction effectively and improve the solubility remarkably .…”

Section: Introductionmentioning

confidence: 99%

Structure, thermal stability, electrochemical behaviors, and mechanical properties of organosoluble polyimide with pyrimidine ring in the main chain

2016

J of Applied Polymer Sci

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A novel organosoluble polyimide (PI) with pyrimidine ring in the main chain was synthesized by chemical and thermal imidization, respectively, from 3,3 0 ,4,4 0 -benzophenone tetracarboxylic dianhydride and 2,4-diamino-6-chloropyrimidine as raw materials and its molecular structure, solubility, UV-visible absorption characteristic, crystallinity, thermal stability, electrochemical behaviors, and mechanical properties were also studied. It was found that the introduction of pyrimidine ring in the main chain could increase the solubility of PI in polar aprotic solvents at room temperature and 60 8C, respectively, because of its molecular main chain with asymmetric structure and two polar N atoms in pyrimidine ring. Furthermore, PI had strong optical absorption peak intensity, excellent thermal stability, good redox reversibility, especially outstanding mechanical properties, which were conductive to its potential applications in adhesives, polyelectrolyte, separation membrane, and so on. V C 2016 Wiley Periodicals, Inc. J.Appl. Polym. Sci. 2016, 133, 43680.

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Section: Introductionmentioning

confidence: 99%

Structure, thermal stability, electrochemical behaviors, and mechanical properties of organosoluble polyimide with pyrimidine ring in the main chain

2016

J of Applied Polymer Sci

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“…In the past few years, many chemical modifications have been reported in the literature to obtain soluble PIs/PAIs by impregnation of nanoparticles, [11,12] incorporation of flexible linkages, [13] formation of metal organic framework, [14] and use of unsymmetrical [15] or fluorinated [16] diamine structures, etc. Most of these approaches to obtain soluble polymers were aimed at reduction of several types of chain-chain interactions, such as chain packing (e.g., crystallinity), charge transfer, and electronic polarization interaction.…”

Section: Introductionmentioning

confidence: 99%

Thermal Cycloimidization Study of Polyimides and Poly(amide imide)s Synthesized from Low-Temperature Solution Polymerization

Dodda

Remiš

Martı́n

et al. 2015

Journal of Macromolecular Science, Part B

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Polyimides (PI)s and Poly(amide imide)s (PAI)s containing di/tri-structural arrangements of monomer constituents were synthesized from 1,2,4,5 benzenetetracarboxylic anhydride/3,3 0 ,4,4 0 benzophenonetetracarboxylic dianhydride, diamines and trimellitic dianhydride chloride, i.e., a mixture of dianhydrides and diamines, using low-temperature solution polymerization. The majority of the resulting polymers were readily soluble in polar aprotic solvents such as dimethylformamide, dimethylsulfoxide, dimethylacetamide, etc. Thermal cycloimidization studies by thermogravimetic analysis (TGA) and Fourier transform infrared spectroscopy (FT-IR) revealed that the rate of cycloimidization was much faster during the initial 15 min, and then occurred at much slower rates till the completion. The activation energies (Ea) for thermal cycloimidization of poly(amic acid)s was calculated from the rate of mass loss of the polymer heated at different temperatures according to the Coats and Redfern method. PI and PAIs derived from diamines containing single cyclic/benzene ring structures, such as mphenylenediamine and 1,3-cyclohexanebis(methylamine), showed less amount of char yield than those having two benzene rings and separated by methylene, sulfone, or ether linkages. The structure of both diamine and trimellitic chloride had a profound effect on the polymer chain mobility, as indicated by the big variation in the glass transition temperatures. Thermally stable polymers were developed into membranes and tested for their mechanical strength by dynamic mechanical analysis(DMA).

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“…Aromatic polyimide (PI) has received considerable attention for its potential application in aerospace, microelectronics, optoelectronics, composites, and so on due to its low dielectric constant, excellent dimensional stability, strong solvent resistance, and outstanding thermal and mechanical properties . Since the Kapton ® PI films were commercialized by DuPont in the early 1960s, a number of aromatic PIs have been reported .…”

Section: Introductionmentioning

confidence: 99%

The pyrolysis behaviors of ternary copolyimide derived from aromatic dianhydride and aromatic diisocyanates

Guo

Chen

et al. 2013

J of Applied Polymer Sci

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A polyimide (PI) based on benzophenone-3,3 0 ,4,4 0 -tetracarboxylic acid dianhydride, toluene diisocyanate (TDI), and 4,4 0 -methylenebis (phenyl isocyanate) (MDI) has been synthesized via a one-step polycondensation procedure. The resulting PI possessed excellent thermal stability with the glass transition temperature (T g ) 316 C, the 5% weight loss temperature (T 5% ) in air and nitrogen 440.4 C and 448.0 C, respectively. The pyrolysis behaviors were investigated with dynamic thermogravimetric analysis (TGA), TGA coupled with Fourier transform infrared spectrometry (TGA-FTIR) and TGA coupled with mass spectrometry (TGA-MS) under air atmosphere. The results of TGA-FTIR and TGA-MS indicated that the main decomposition products were carbon dioxide (CO 2 ), carbonic oxide (CO), water (H 2 O), ammonia (NH 3 ), nitric oxide (NO), hydrogen cyanide (HCN), benzene (C 6 H 6 ), and compounds containing NH 2 , CBN, N@C@O or phenyl groups. The activation energy (E a ) of the solid-state process was estimated using Ozawa-Flynn-Wall (OFW) method which resulted to be 143.8 and 87.8 kJ/mol for the first and second stage. The pre-exponential factor (A) and empirical order of decomposition (n) were determined by Friedman method. The activation energies of different mechanism models were calculated from Coats-Redfern method. Compared with the activation energy values obtained from the OFW method, the actual reaction followed a random nucleation mechanism with the integral form g(a) 5 2ln(1 2 a).

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Synthesis and properties of organosoluble polyimides based on novel perfluorinated monomer hexafluoro-2,4-toluenediamine

Cited by 31 publications

References 41 publications

Structure, thermal stability, electrochemical behaviors, and mechanical properties of organosoluble polyimide with pyrimidine ring in the main chain

Structure, thermal stability, electrochemical behaviors, and mechanical properties of organosoluble polyimide with pyrimidine ring in the main chain

Thermal Cycloimidization Study of Polyimides and Poly(amide imide)s Synthesized from Low-Temperature Solution Polymerization

The pyrolysis behaviors of ternary copolyimide derived from aromatic dianhydride and aromatic diisocyanates

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