Soluble Polyimides from Unsymmetrical Diamine with Trifluoromethyl Pendent Group

Chung, Il-Moon; Kim, Sang Youl

doi:10.1021/ma991561h

Cited by 195 publications

(124 citation statements)

References 32 publications

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“…These dinitrobisimides were synthesized from the imidation reaction of four pyridine containing diamines (DA 1-4 ) based on 4-aryl-2,6-bis(4-aminophenyl)pyridines and 3-nitro phthalic anhydride. The resulting poly(ether-imide)s (PEI [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16] ) showed good thermal stability as well as good solubility in common organic solvents.…”

Section: Discussionmentioning

confidence: 99%

“…The other 15 poly(ether-imide)s (PEI [2][3][4][5][6][7][8][9][10][11][12][13][14][15][16] ) were prepared by the same procedure using appropriate dinitrobisimides and four different aromatic diols (DO 1-4 ). All synthesized polymers were characterized by FT-IR and 1 H-NMR spectroscopy ( Table 2).…”

Section: Preparation Of Poly(ether-imide)s: Poly(ether-imide) From Thmentioning

confidence: 99%

“…• C, which indicated excellent thermal 12 + + + + ± ± ± PEI 13 + + + + ± ± ± PEI 14 + + + + ± --PEI 15 + + + + ± ± ± PEI 16 + + + + ± ± ± +, soluble at room temperature; ±, partially soluble when warmed; -, insoluble. …”

Section: Scheme 2 Preparation Of Diamic Acids and Subsequent Chemicamentioning

confidence: 99%

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Synthesis and characterization of new thermally stable poly(ether-imide)s derived from 4-aryl-2,6-bis[4-(3-nitrophthalimido)phenyl] pyridines

Tamami

Koohmareh

2007

Designed Monomers and Polymers

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Abstract-A series of thermally stable poly(ether-imide)s (PEI 1−16 ) bearing bulky aryl pendant groups were synthesized by nitro-displacement condensation of a new series of dinitrobisimide monomers, namely 4-aryl-2,6-bis[4-(3-nitrophthalimido)phenyl]pyridines (DNBI 1-4 ), with commercially available aromatic diols (DO 1-4 ). These dinitrobisimides were prepared from the reaction of 4-aryl-2,6-bis(4-aminophenyl)pyridines (DA 1-4 ) and 3-nitrophthalic anhydride in N,N-dimethyl acetamide. A model compound was synthesized by reaction of DNBI 1 with phenol in the presence of potassium carbonate in dimethyl formamide and the resulting bis(ether-imide) derivative was obtained in high yield. These polymers were characterized by FT-IR, 1 H-NMR and elemental analysis, and their physical properties, including solution viscosity, solubility properties and thermal stabilities, were studied. The synthesized PEIs show excellent thermal stability and solubility in polar aprotic solvents.

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Section: Discussionmentioning

confidence: 99%

Section: Preparation Of Poly(ether-imide)s: Poly(ether-imide) From Thmentioning

confidence: 99%

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Synthesis and characterization of new thermally stable poly(ether-imide)s derived from 4-aryl-2,6-bis[4-(3-nitrophthalimido)phenyl] pyridines

Tamami

Koohmareh

2007

Designed Monomers and Polymers

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“…Recently, it is well recognized that asymmetric introduction of bulky substituents or linkages into polyimide backbone is an another effective approach to improve the solubility of polyimides [34][35][36][37][38][39][40]. Various asymmetric diamines were designed and used for organosoluble PI preparation.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Highly Organosoluble Polyimides Based on a New Asymmetric Dianhydride

Zeng

Zhou

Fan

et al. 2012

Designed Monomers and Polymers

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A new asymmetric biphenyl dianhydride, 2-o-tert-butylphenoxy-4,4 ,5,5 -biphenyltetracarboxylic dianhydride, was readily synthesized via a four-step route. The key intermediate, 2-nitro-bis(N-methylphthalimide) (2), was synthesized at low temperature (around 15 • C), with a yield of over 90%, which enhances the molecular adjustment flexibility of the monomer. FT-IR and 1 H-NMR were used to fully verify the proposed structure of this new asymmetric dianhydride. The polyimides were prepared from such new dianhydride and commercial diamines by high-temperature one step polymerization in m-cresol. The molecular structures of the polymers were determined by FT-IR and 1 H-NMR. The inherent viscosities were in the range of 0.40-0.41. The polymers show high organosolubility in common solvents such as NMP, CHCl 3 and THF. TGA analysis revealed that the polymers displayed good thermal stability up to 490 • C. © Koninklijke Brill NV, Leiden, 2012

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“…3 For example, polyimides containing trifluoromethyl groups showed high modulus, low thermal expansion coefficient, and good solubility,4-7 and incorporation of heterocyclic units into polyimide chains increased the glass transition temperature and thermooxidative stability_s-u Recently, we succeeded in synthesis of new soluble polyimides from the unsymmetrical diamine containing trifluoromethyl groups at 2-position of 4,4'-diaminodiphenyl ether. 12 These polyimides have improved solubility and their thermal properties are comparable to those of the polyimides without trifluoromethyl groups. Therefore, it is interesting to attach a cyano group, which is smaller than trifluoromethyl group but has stronger electron withdrawing characteristics, to the rigid aromatic polyimides not only because the cyano group may interfere chain interactions of the rigid polyimides but also because it can be transformed into other functional group.…”

mentioning

confidence: 99%

Synthesis and Characterization of Polyimides from Unsymmetrical Diamine with Cyano Groups

Kang

Chung

Kakimoto

et al. 2001

Polym J

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ABSTRACT:A new diamine monomer containing cyano group, 2-cyano-4,4' -diaminodiphenyl ether, was synthesized and polymerized to polyimides with several aromatic dianhydrides via two kinds of imidization methods, namely, thermal or solution imidization methods. By the thermal imidization method, tough, flexible, and creasable polyimide films were obtained except the polyimide from pyromellitic dianhydride. The polyimides have high Tg values and are stable up to 500°C in air. The polyimide made from the diamine and 4,4'-oxyphthalic anhydride via solution imidization method was partially soluble in polar aprotic solvents, but it becomes soluble when the cyano groups are hydrolyzed.KEY WORDS Polyimide / Unsymmetrical Diamine / 2-Cyano-4,4'-diaminodiphenyl Ether/ Solution Imidization / Recent technological advances in space and other areas have generated a continuing and growing need for materials that withstand prolonged exposures at temperature in excess of 300°C and/or relatively short exposures at much higher temperature. The need has become particularly acute for high temperature materials used in electrical and thermal insulation, gaskets, flexible tubing, advanced composites and many other items. Among high temperature polymers, aromatic polyimides were developed in the early 1960s and since then have been of great technological importance due to their high temperature stability, 1 • 2 favorable dielectric properties and chemical resistance. And now aromatic polyimides find many applications in the composites and microelectronics.However, most ofpolyimides encounter processing difficulties due to their infusibility and poor solubility in organic solvents that mainly come from strong interchain forces and chain rigidity. A great deal of research effort on the polyimides has been concerned on improvement of processability and other properties with minimal effect on thermal stability. 3 For example, polyimides containing trifluoromethyl groups showed high modulus, low thermal expansion coefficient, and good solubility,4-7 and incorporation of heterocyclic units into polyimide chains increased the glass transition temperature and thermooxidative stability_s-u Recently, we succeeded in synthesis of new soluble polyimides from the unsymmetrical diamine containing trifluoromethyl groups at 2-position of 4,4'-diaminodiphenyl ether. 12 These polyimides have improved solubility and their thermal properties are comparable to those of the polyimides without trifluoromethyl groups. Therefore, it is interesting to attach a cyano group, which is smaller than trifluoromethyl group but has stronger electron withdrawing characteristics, to the rigid aromatic polyimides not only because the cyano group may interfere chain interactions of the rigid polyimides but also because it can be transformed into other functional group. In this study, new diamine monomer containing cyano group, 2-cyano-4,4' -diaminodiphenyl ether (2) was synthesized and polymerized with several dianhydrides, and the effect of the pendent cyano groups on the ...

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Soluble Polyimides from Unsymmetrical Diamine with Trifluoromethyl Pendent Group

Cited by 195 publications

References 32 publications

Synthesis and characterization of new thermally stable poly(ether-imide)s derived from 4-aryl-2,6-bis[4-(3-nitrophthalimido)phenyl] pyridines

Synthesis and characterization of new thermally stable poly(ether-imide)s derived from 4-aryl-2,6-bis[4-(3-nitrophthalimido)phenyl] pyridines

Synthesis and Characterization of Highly Organosoluble Polyimides Based on a New Asymmetric Dianhydride

Synthesis and Characterization of Polyimides from Unsymmetrical Diamine with Cyano Groups

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