Synthesis and Properties of Novel Polyimides Containing Fluorinated Alkoxy Side Groups

Bes, Laurence; Rousseau, Alain; Boutevin, Bernard; Merçier, Régis; Kerboua, Rachid

doi:10.1002/1521-3935(20011001)202:14<2954::aid-macp2954>3.0.co;2-9

Cited by 16 publications

(3 citation statements)

References 15 publications

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“…The incorporation of ether groups or other flexibilizing linkages into the main chain generally leads to lower glass transition temperature as well as a significant improvement in solubility without greatly sacrificing other advantageous polymer properties. 4–7 On the other hand, the introduction of bulky groups into the polymer chain 8–13 or the attachment of bulky lateral groups 14–21 can impart a significant increase in T g by restricting the segmental mobility, while providing an enhanced solubility due to decreasing packing and crystallinity. Combining these two structural modifications minimized the trade-off between the processability and useful/positive properties of aromatic polyimides.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and evaluation of properties of novel aromatic poly(ether-imide) with benzazole pendent groups and flexible ether linkages

Toiserkani

2011

High Performance Polymers

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Three types of new bis(ether-amine) monomers such as 5-(2-benzimidazole)-1,3-bis(4-aminophenoxy)benzene (3), 5-(2-benzoxazole)-1,3-bis(4-aminophenoxy)benzene (4), and 5-(2-benzothiazole)-1,3-bis(4-aminophenoxy)benzene (5) were prepared in three steps, starting from the reaction of 3,5-dihydroxybenzioc acid with 4-fluronitrobenzene in N, N-dimethylformamide (DMF) solution in the presence of potassium carbonate, followed by catalytic reduction of the intermediate dinitro-carboxylic acids, and subsequent condensation of the resulting diamino-carboxylic acids and 1,2-phenylenediamine, 2-aminophenol or 2-aminothiophenol in polyphosphoric acid (PPA), respectively. Three series of modified poly(ether-imide)s (PEIs) bearing pendent benzimidazole, benzoxazole or benzothiazole groups were prepared from the bis(ether-amine)s with dianhydrides by a conventional two-stage process that included ring-opening polycondensation forming the poly(amic acid)s (PAA) and further thermal or chemical imidization forming poly(ether-imide)s. For comparative purposes, reference poly(ether-imide)s were also prepared by reacting bis(ether-amine) lacking pendent groups namely 1,3-bis(4-aminophenoxy)benzene (6) with the same dianhydrides under similar conditions. The modified polymers were obtained in quantitative yields with inherent viscosities between 0.52 and 0.83 dL g−1. Experimental results indicated that all the PEIs had glass transition temperature between 221 and 283 °C, the decomposition temperature at 10% weight loss between 480 and 572 °C under nitrogen.

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Section: Introductionmentioning

confidence: 99%

Synthesis and evaluation of properties of novel aromatic poly(ether-imide) with benzazole pendent groups and flexible ether linkages

Toiserkani

2011

High Performance Polymers

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“…Considering the two most routinely practiced routes for the synthesis of polyimides, namely, the diamine–dianhydride reaction and the diisocyanate–dianhydride reaction, three options are available for attaching flexible side chains to aromatic polyimides. These are (1) diamine modification,10–12 (2) dianhydride modification,9 and (3) diisocyanate modification 13–18…”

Section: Introductionmentioning

confidence: 99%

Polyimides based on aromatic diisocyanates containing pendent flexible alkoxy chains and aromatic dianhydrides: Synthesis, characterization, and liquid‐crystal alignment properties

Sarkar¹,

Halhalli²,

Kulkarni³

et al. 2009

J of Applied Polymer Sci

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Four new aromatic diisocyanates containing pendent flexible alkoxy chains, namely, 5-butyloxy-1,3-phenylenediisocyanate, 5-octyloxy-1,3-phenylenediisocyanate, 5-dodecyloxy-1,3-phenylenediisocyanate, and 5-hexadecyloxy-1,3-phenylenediisocyanate, were synthesized by Curtius rearrangement of the corresponding 5-alkoxy-1,3-phenylene diacylazides. These diisocyanates were each polycondensed with three commercially available aromatic dianhydrides: 4,4 0 -oxydiphthalic anhydride, 3,3 0 ,4,4 0 -(hexafluoroisopropylidene) diphthalic anhydride, and 3,3 0 ,4,4 0 -benzophenonetetracarboxylic dianhydride-in benzonitrile in the presence of 1,4-diazabicyclo[2.2.2]octane as a catalyst to obtain a series of polyimides with inherent viscosities in the range 0.16-0.43 dL/g. Except for 3,3 0 ,4, 4 0 -benzophenonetetracarboxylic dianhydride based polyimides, all of the polyimides were found to be soluble in dichloromethane, m-cresol, 1-methyl-2-pyrrolidinone, tetrachloroethane, and pyridine either at room temperature or on heating and could be cast into tough, flexible, transparent films from a solution in m-cresol or tetrachloroethane. X-ray diffractograms revealed that the polyimides with longer alkoxy chains had layered structures. The glasstransition temperature of the polyimides containing pendent flexible alkoxy chains were in the range 159-246 C as measured by differential scanning calorimetry. The temperature for the 10% weight loss of the polyimides was in the range 410-460 C in a nitrogen atmosphere, which indicated good thermal stability. A pretilt angle of 2.97 was observed for the polyimide derived from 5-octyloxy-1, 3-phenylenediisocyanate and 4,4 0 -oxydiphthalic anhydride.

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“…Although standard aromatic PIs can meet most desired properties, some requirements, such as high optical transparency, low fabricating temperature, good processability, and, in some cases, low dielectric constant, have to be addressed before their final acceptance in these fields. To overcome the bottlenecks of standard PIs, a variety of modifications have been performed, among which fluorination might be one of the most effective 3, 8–19. Fluoro‐containing substituents, including fluorine atoms or fluoroalkyl groups (e.g., CF 3 ), possess large electronegativities and low molar polarizations and, thus, often endow fluoropolymers with good optical transparency [both in the scope of the ultraviolet–visible (UV–vis) region and optocommunication wavelength], low humidity absorption, low refractive index, and low dielectric constant 17–19.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and properties of fluorinated polyimides from 1,1‐bis(4‐amino‐3,5‐dimethylphenyl)‐1‐(3,4,5‐trifluorophenyl)‐2,2,2‐trifluoroethane and various aromatic dianhydrides

Zhao

Liu

et al. 2008

J of Applied Polymer Sci

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A novel aromatic diamine, 1,1-bis(4-amino-3,5-dimethylphenyl)-1-(3,4,5-trifluorophenyl)-2,2,2-trifluoroethane, containing a pendant polyfluorinated phenyl group, a trifluoromethyl group, and methyl groups orthosubstituted to the amino groups in the structure was synthesized and characterized. The diamine was polymerized with several aromatic dianhydrides, including 3,3 0 ,4,4 0 -biphenyltetracarboxylic dianhydride, 3,3 0 ,4,4 0 -benzophenonetetracarboxylic dianhydride, 4,4 0 -oxydiphthalic anhydride, and 4,4 0 -hexafluoroisopropylidene diphthalic anhydride, via a high-temperature one-step procedure to afford four polyimides (PIs) with inherent viscosities of 0.47-0.70 dL/g. The PIs exhibited excellent solubilities in a variety of organic solvents. They were soluble not only in polar aprotic solvents but in many common solvents, such as cyclopentanone, tetrahydrofuran, and even toluene at room temperature. The tough and flexible PI films cast from the PI solutions exhibited good thermal stabilities and acceptable tensile properties. The glass-transition temperatures were in the range 312-365 C, and the 5% weight loss temperatures were all higher than 480 C in nitrogen. The films had tensile strengths in the range 76-99 MPa, tensile moduli of 2.2-2.8 GPa, and elongations at break of 5-8%. In addition, the PI films exhibited excellent transparency in the visible light region with cutoff wavelength as low as 302 nm and transmittance higher than 88% at the wavelength of 450 nm. The PI films showed low dielectric constants ranging from 2.50-2.68 and low moisture absorptions of less than 0.56%. The good combined properties of the PIs mainly resulted from the synergic effects of the different substituents. V

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Synthesis and Properties of Novel Polyimides Containing Fluorinated Alkoxy Side Groups

Cited by 16 publications

References 15 publications

Synthesis and evaluation of properties of novel aromatic poly(ether-imide) with benzazole pendent groups and flexible ether linkages

Synthesis and evaluation of properties of novel aromatic poly(ether-imide) with benzazole pendent groups and flexible ether linkages

Polyimides based on aromatic diisocyanates containing pendent flexible alkoxy chains and aromatic dianhydrides: Synthesis, characterization, and liquid‐crystal alignment properties

Synthesis and properties of fluorinated polyimides from 1,1‐bis(4‐amino‐3,5‐dimethylphenyl)‐1‐(3,4,5‐trifluorophenyl)‐2,2,2‐trifluoroethane and various aromatic dianhydrides

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