Preparation and Properties of Poly(enaryloxy nitriles) Containing Schiff Bases

Kim, Sang-Gon; Lee, Seung-Jae; Gong, Myoung‐Seon

doi:10.1021/ma00120a032

Cited by 6 publications

(4 citation statements)

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“…In the NMR spectra of the model compound 3, the phenyl proton in the fragment of 1 appeared at 7.82-7.51 ppm, whereas those of tyramine are present at 7.23-6.82 ppm. In the 13 C NMR spectrum, signals appeared at 29.2 (-CH2 The solubility of polymers containing dicyanovinyl group was investigated. In the case of polymer 4, solubility in THF and acetone was variable according to isolation of synthesized polymers from the reaction mixture.…”

Section: Resultsmentioning

confidence: 99%

New Method for the Preparation of Poly(enamino-enaryloxynitriles) by Interfacial Polymerization and Thermal Properties

Lee

Geum

Gong

2001

Polym J

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Section: Resultsmentioning

confidence: 99%

New Method for the Preparation of Poly(enamino-enaryloxynitriles) by Interfacial Polymerization and Thermal Properties

Lee

Geum

Gong

2001

Polym J

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“…Therefore, these interesting properties have so far been estimated using powdery or spin-coated samples in almost all cases. Recently, much effort has been put forth on synthesizing soluble polyazomethines with film formability. − Suematsu and co-workers reported the synthesis of some film-forming aromatic polyazomethines using m -cresol as a polymerization medium, whereas some polyazomethines precipitated from m -cresol as a colored powder during the polymerization process . Other methods have been also reported to improve the processability of conjugated polyazomethines by modification and selection of the polymer structure, for example, unsymmetrical or symmetrical , substitutions in the main chain aromatic rings with flexible alkyl or alkoxy side chains.…”

Section: Introductionmentioning

confidence: 99%

Fully Conjugated and Soluble Polyazomethines

1997

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Fully conjugated and soluble polyazomethines were synthesized by the polycondensation of aromatic dialdehydes with two kinds of diamines having a tetraphenylethylene structure, cis- and trans-1,2-bis(4-aminophenyl)-1,2-diphenylethylene (4a and 4b). The structures of these diamines were determined using NMR and single crystal X-ray analysis. The diamines formed 1:1 complexes with toluene which was used as a recrystallization solvent. The polyazomethines, as precipitated, possessed inherent viscosities (ηinh) in the range from 0.83 to 0.98 dL/g. Polymers 6 and 7, which were prepared from 4a and terephthalaldehyde and from 4b and isophthalaldehyde, respectively, gave flexible and tough orange films. These polymer films exhibited excellent solubility in common organic solvents such as benzene, chloroform, and THF. The molecular weights of the polymers increased 2- to 4-fold by postcuring at 200 °C. Although the crystallinity of polymer 6 was slightly higher than that of polymer 7, these polymers were essentially amorphous. All of the polyazomethines showed excellent thermal stability with no significant weight loss up to approximately 350 °C, and the 5% weight loss temperatures in air were over 400 °C. The polymer films had glass transition temperatures over 260 °C.

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“…[2][3][4][5][6][7][8][9][10][11] Polyenaryloxynitriles could be produced by interfacial polymerization of 2 and aromatic diols. [12][13][14][15][16][17] From the previous study on the dicyanovinyl-containing polymers, we obtained a series of poly(enamino-enaryloxynitriles)s by copolymerization of 2 with aromatic diamine and diphenol 18,19 or interfacial polymerization of 2 with aliphatic amine-containing phenol monomers.…”

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confidence: 99%

“…The decarboxylation reaction assumed to proceed at a temperature of endotherm and followed by intramolecular cyclization or cross-linking of the dicyanovinyl group during heating at a temperature of the maximum exotherm. [1][2][3][4][5][6][7][8][9][10][11] The cured poly(enamino-enaryloxynitriles) should have complex network structures.…”

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confidence: 99%

Preparation of Novel Tyrosine-Based Polymers and Thermal Properties

2002

Bulletin of the Korean Chemical Society

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Since the first notable condensation polymerization of dicyanovinyl monomer, 1 typically p-bis(1-chloro-2,2-dicyanovinyl)benzene (2), several kinds of dicyanovinyl-containing polymers using 2 were reported by many researchers. 2-11Polyenaryloxynitriles could be produced by interfacial polymerization of 2 and aromatic diols. 12-17From the previous study on the dicyanovinyl-containing polymers, we obtained a series of poly(enamino-enaryloxynitriles)s by copolymerization of 2 with aromatic diamine and diphenol 18,19 or interfacial polymerization of 2 with aliphatic amine-containing phenol monomers. 20 In this way, we could simultaneously incorporate enaminonitriles and enaryloxynitirles or arylate and amide units into polymer backbone to produce new poly(enamino-enaryloxynitriles) or poly(arylate-amide).The dicyanovinylidine group (C=C(CN) 2 ) can be considered structurally equivalent to the carbonyl group in reactions where the two functional groups have similar inductive and resonance effects. 21 Thus, polyenaminonitriles and polyenaryloxynitriles can be considered analogous to polyamides and polyarylates.This work deals with the preparation of tyrosine-based poly(enamino-enaryloxynitriles) and poly(arylate-amide) by reacting tyrosine with 2 and terephthaloyl chloride using interfacial polymerization, and the decarboxylation reaction followed by curing reaction. Model compounds N-(1-phenyl-2,2-dicyanovinyl)-p-(1-phenyl-2,2-dicyanovinyloxy)benzyl glycine (5) and N-benzoyl-4-benzoyloxybenzyl glycine (6) were prepared by phase transfer reaction of tyrosine with 1-chloro-1-phenyl-2,2-dicyanoethene (1) and benzoyl chloride, respectively. The model reaction was based on a representative procedure for the interfacial technique using two phases solvent system. The reaction was nearly complete within 3 min to form the model compounds 5 and 6 at room temperature. After recrystallization, moderate yields of 5 and 6 were obtained after acidification as illustrated in Scheme 1.In the ability as a conjugate base, alkyl amine (RNH 2 ) is similar to phenoxide.22 Thus amino alkyl-containing phenol derivatives can be used as monomers for the poly(enaminoenaryloxynitriles) and poly(arylate-amide). The interfacial condensation polymerization of 2 and terephthaloyl chloride proceeded in the presence of a phase transfer agent in a twophases solvent system as shown in Scheme 2 and 3.The polymerization results are summarized in Table 1. The polymers obtained here were identified as poly(enaminoenaryloxynitriles) 7 and poly(arylate-amide) 8 by comparing IR and NMR spectra with those of model compound 5. In Scheme 1Scheme 2

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Preparation and Properties of Poly(enaryloxy nitriles) Containing Schiff Bases

Cited by 6 publications

References 1 publication

New Method for the Preparation of Poly(enamino-enaryloxynitriles) by Interfacial Polymerization and Thermal Properties

New Method for the Preparation of Poly(enamino-enaryloxynitriles) by Interfacial Polymerization and Thermal Properties

Fully Conjugated and Soluble Polyazomethines

Preparation of Novel Tyrosine-Based Polymers and Thermal Properties

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