Poly(1,3,4‐oxadiazole) fibers: New fibers with superior high temperature resistance

Frazer, A. H.; Wallenberger, Frederick T.

doi:10.1002/pol.1964.100020314

Cited by 41 publications

(29 citation statements)

References 7 publications

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“…1,2 They are considered to be interesting alternatives for the development of high temperature and flame resistant fibers, 3,4 or thermally stable membranes for gas separation. 5 In addition, oxadiazole-based polymers have been widely investigated in the field of polymer light-emitting diodes as well as other fields of polymer electronics.…”

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confidence: 99%

A New Class of Aromatic Poly(1,3,4-oxadiazole)s and Poly(amide-1,3,4-oxadiazole)s Containing (Naphthalenedioxy)diphenylene Groups

Hsiao

Liou

2002

Polym J

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ABSTRACT:Polyhydrazides and poly(amide-hydrazide)s having inherent viscosities of 0.31-1.17 dL g −1 were prepared from two ether-naphthalene-dicarboxylic acids, 4,4'-(1,5-naphthalenedioxy)dibenzoic acid (1,5-NDA) and 4,4'-(2,3-naphthalenedioxy)dibenzoic acid (2,3-NDA) with terephthalic dihydrazide, isophthalic dihydrazide, and paminobenzhydrazide via the phosphorylation polycondensation reaction. Except for one example, the hydrazide polymers were essentially amorphous and readily soluble in polar organic solvents such as N-methyl-2-pyrrolidone (NMP) and N,N-dimethylacetamide (DMAc). They could be cast into transparent, flexible, and tough films with good mechanical strengths from solution in DMAc. These hydrazide polymers exhibited glass-transition temperatures (T g s) in the range 179-190• C and could be thermally cyclodehydrated into the corresponding poly(1,3,4-oxadiazole)s and poly(amide-1,3,4-oxadiazole)s in the solid state at elevated temperatures. The oxadiazole polymers had T g s of 228-242• C (by differential scanning calorimetry) and 10% weight loss temperatures above 500• C, as revealed by thermogravimetric analysis in nitrogen or in air. KEY WORDS Naphthalenedioxy / Polyhydrazide / Poly(amide-hydrazide) / Poly(1,3,4-oxadiazole) / Poly(amide-1,3,4-oxadiazole) / Aromatic poly(1,3,4-oxadiazole)s are a class of chemically resistant and thermally stable heterocyclic polymers. 1, 2 They are considered to be interesting alternatives for the development of high temperature and flame resistant fibers, 3, 4 or thermally stable membranes for gas separation. 5 In addition, oxadiazole-based polymers have been widely investigated in the field of polymer light-emitting diodes as well as other fields of polymer electronics. 6-11 Unfortunately, aromatic polyoxadiazoles are difficult to process owing to their infusible and insoluble properties and their tendency to be brittle. Many efforts have been made to improve the solubility and lower the T g , hence to make such polymers more easily processable, for example by incorporating flexible linkages in the backbone or bulky pendant group on the aromatic rings. [12][13][14][15][16][17][18] Several different reaction pathways have been developed to prepare poly(1,3,4-oxadiazole)s. The most popular synthesis involves the preparation of a precursor polyhydrazide by the reaction of a diacyl chloride or derivative with hydrazine or a dihydrazide compound. This precursor polyhydrazide is cyclized to the polyoxadiazole by heating to 200-300 • C under vacuum or heating in a dehydrating solvent such as sulfuric acid, polyphosphoric acid, or phosphoryl chloride. [19][20][21] A different synthetic procedure produces polyoxadiazoles in one step by the solution polymerization of a dicarboxylic acid or the corresponding nitrile, amide, or ester with hydrazine or its salt in polyphosphoric or sulfuric acid or a phosphorus pentoxide/methanesulfonic acid mixture. 16,22,23 In addition, aromatic polyether synthesis through aromatic nucleophilic displacement reaction has been used for the ...

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A New Class of Aromatic Poly(1,3,4-oxadiazole)s and Poly(amide-1,3,4-oxadiazole)s Containing (Naphthalenedioxy)diphenylene Groups

Hsiao

Liou

2002

Polym J

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“…3,3',4,4'-benzophenone tetracarboxylic dianhydride (Merck) was recrystallized from acetic anhydride. 1 H NMR spectra were recorded on 400 MHz Bruker instrument, using CDCl 3 or DMSO-d 6 as solvent and tetramethylsilane as shift reference (tube diameter 5 mm). IR spectra were recorded on a Shimadzu FT/IR-680 plus instrument, using KBr pellets.…”

Section: Materials and Measurementsmentioning

confidence: 99%

Synthesis and Characterization of Novel Poly(hydrazide-imide)s incorporating L-Alanine

Hajipour

Zahmatkesh

Ruoho

2008

High Performance Polymers

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This deals with the polycondensation between a chiral diacyl chloride, (N,N'-(3,3',4,4'-benzophenonetetracarboxylic)-3,3',4,4'-diimido-di-L-alanine chloride) and six different dihydrazides. The corresponding poly(hydrazide-imide)s, which have been obtained by two methods in quantitative yields, are moderately soluble in polar aprotic solvents, have good thermal stability and exhibit optical activity. The synthetic compounds have been characterized by IR, UV and 1 H NMR spectroscopy, elemental analysis and specific rotation. The thermal properties of the poly(hydrazide-imide)s have been studied by thermogravimetric analysis and differential scanning calorimetry.

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“…Polysemicarbazides with linear linkage -CO-NHcan be prepared from diisocyanate and dihydrazide via addition reaction [16][17][18][19] . They display widely biological activities for the application of enzymatic quasi reagents [20,21] , ureapeptoid peptidomimetics [22,23] and antibacterial Co, Cu, Ni, and Zn complexes [24,25] .…”

Section: Introductionmentioning

confidence: 99%

Photochromic azo polysemicarbazides with biocompatibility behavior

Liu

Xiong

Dong

et al. 2010

J. Wuhan Univ. Technol.-Mat. Sci. Edit.

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Two kinds of azo polysemicarbazides were prepared based on 3, 3'-azobis (benzoylhydrazide) (ABH) and two kinds of diisocyanates via solution polymerization. The structures were characterized by Fourier-transform infrared (FT-IR) technique and elemental analysis. Inherent viscosities of the polymers were 0.32 and 0.29 dL/g and both could be dissolved in H 2 SO 4 and polar organic solvents. Thermal gravimetric analysis (TGA) presented a multi-step degradation and a decomposition temperature range of 230-280 ℃. And photoisomerization of the azo polymers in solvent of N, N-dimethyl acetamide (DMAc) was confirmed by Ultraviolet-visible spectroscopy (UV-Vis), suggested the isomerization appearing under the ultraviolet irradiation at 365 nm and recovering completely by visible light irradiation or kept in the dark. Transmission electron microscopy (TEM) of polysemicarbazides before and after soaking in bovine serum albumin (BSA) solution confirmed the biocompatibility of azo polymers.

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Poly(1,3,4‐oxadiazole) fibers: New fibers with superior high temperature resistance

Cited by 41 publications

References 7 publications

A New Class of Aromatic Poly(1,3,4-oxadiazole)s and Poly(amide-1,3,4-oxadiazole)s Containing (Naphthalenedioxy)diphenylene Groups

A New Class of Aromatic Poly(1,3,4-oxadiazole)s and Poly(amide-1,3,4-oxadiazole)s Containing (Naphthalenedioxy)diphenylene Groups

Synthesis and Characterization of Novel Poly(hydrazide-imide)s incorporating L-Alanine

Photochromic azo polysemicarbazides with biocompatibility behavior

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