Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – From phenol – phenol ether – or inorganic phenolate
Patent
1991-06-06
1993-08-10
Anderson, Harold D.
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
From phenol, phenol ether, or inorganic phenolate
528 86, 528183, 528186, 528210, 528336, 528337, 528342, 528397, 528422, C08G 7300, C08G 7532
Patent
active
052350231
DESCRIPTION:
BRIEF SUMMARY
FIELD OF THE ART
The invention relates to the synthesis of polybenzoxazole, polybenzimidazole and polybenzothiazole polymers.
BACKGROUND OF THE INVENTION
Polybenzoxazole (PBO), polybenzimidazole (PBI) and polybenzothiazole (PBT) and related polymers (hereinafter referred to as PBZ polymers) are known polymers which can be extruded as fibers or films having a high tensile strength and high tensile modulus which are useful for structural applications. It is known in the art to synthesize PBZ polymers by the reaction of a first monomer having a primary amine group and a hydroxy, thio or amine group bonded to an aromatic group in ortho position with respect to each other, and a second monomer having an "electron-deficient carbon group". Known electron-deficient carbon groups are set out in Table I hereinafter.
TABLE I ______________________________________
--COOH --CSSH --COBR --CSI
--CSOH --COCO --CSBR CONHR.sub.1
--COSH --CSCO --COI --CS
--CN
______________________________________
and Products, U.S. Pat. No. 4,703,103 (Oct. 27, 1987); Tsai et al., Method
for Making Heterocyclic Block Copolymer, U.S. Pat. No. 4,578,432 (Mar. 25,
1986); Wolfe et al., Liquid Crystalline Poly(2,6-Benzothiazole)
Compositions, Process and Products, U.S. Pat. No. 4,644,724 (Aug. 6,
1985); Wolfe, Liquid Crystalline Polymer Compositions, Process and
Products, U.S. Pat. No. 4,533,693 (Aug. 6, 1985) and Wolfe et al., Liquid
Crystalline Polymer Compositions and Process and Products, U.S. Pat. No.
4,533,692 (Aug. 6, 1985), which are incorporated herein by reference.
In most commonly used monomers, the electron-deficient carbon group is either a carboxylic acid group or a carboxylic acid halide group. For instance, monomers may be 4-hydroxy-5-aminobenzoic acid, terephthalic acid, or terephthaloyl chloride.
Several problems are associated with the known monomers. Acids such as terephthalic acid are highly insoluble in solvents which will dissolve the polymer, so that they must be micronized to produce PBZ polymers of high molecular weight. Acid chlorides such as terephthaloyl chloride are moisture sensitive and can sublime easily. What is needed is a process to synthesize PBZ polymers using monomers having electron-deficient carbon groups which are not moisture sensitive and do not require physical micronization prior to their use in the reaction.
SUMMARY OF THE INVENTION
The present invention is a process for synthesizing PBZ polymers comprising the step of contacting: o-amino-basic moiety contains both: ortho to said first primary amine group; and either: group or an alkali metal carboxylate group, under reaction conditions; group or an alkali metal carboxylate group bonded to said divalent organic moiety; and either: the first electron-deficient carbon group; or an aromatic group, aspects of the present invention are: 1) a polymer dope made by the present process comprising a PBZ polymer and a mineral acid; 2) a PBZ polymer made by the present process; and 3) a shaped article, such as a fiber or a film, comprising a PBZ polymer made by the present process.
The process of the present invention forms PBZ polymers similar to those already known and described in the literature. However, monomers containing electron-deficient carbon groups used in the present invention need not be micronized and are not sensitive to the presence of moisture. Further advantages to the present invention are set out hereinafter.
DETAILED DESCRIPTION OF THE INVENTION
Definitions
The following terms, which are used repeatedly throughout this application, have the meanings and preferred embodiments set out hereinafter unless otherwise specified.
Aromatic group (ar)--any aromatic ring or ring system. Size is not critical as long as the aromatic group is not so big that it prevents further reactions of the moiety in which it is incorporated. Aromatic groups preferably comprise no more than about 18 carbon atoms, more preferably no more than about 12 carbon atoms and most preferably no more than about 6 carbon atoms, not including a
REFERENCES:
patent: 4225700 (1980-09-01), Wolf et al.
patent: 4312976 (1982-01-01), Choe
patent: 4423202 (1983-12-01), Choe
patent: 4608427 (1986-08-01), Sweeny et al.
Anderson Harold D.
The Dow Chemical Company
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