Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – From phenol – phenol ether – or inorganic phenolate
Patent
1995-10-27
1997-10-07
Seidleck, James J.
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
From phenol, phenol ether, or inorganic phenolate
528186, 528193, 528337, 528342, 528423, 528503, 264 51, C08G 7318, C08G 7322
Patent
active
056749694
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/EP94/01302 filed Apr. 22, 1994.
The invention pertains to a rigid rod polymer based on pyridobisimidazole, to a process for the manufacture thereof, to a polymer composition into which such a polymer is incorporated, and to a process for fabricating films, filaments, and yarns therefrom.
Rigid semi-ladder polymers based on pyridobisimidazole have been described, int. al., in U.S. Pat. No. 4,533,692. In claim 100 of said patent publication the homopolymer of tetraaminopyridine and terephthalic acid is claimed. However, it has been found that it is not possible technologically to prepare a polymer based on the latter monomers having an .eta..sub.rel of more than 1.3, or not possible without anything more.
The invention now provides a rigid rod polymer of the known type mentioned in the opening paragraph which can be polymerised to a high degree of polymerisation without any problem and extruded from the polymerisation solution in polyphosphoric acid or spun to form films, filaments, and yarns of exceptionally favourable physical properties. The rigid rod polymer according to the invention is composed of a polymer in which at least 50% of the recurring groups corresponds to the formula: ##STR2##
It should be noted that polymers based on 2,5-dihydroxy-p-phenylene were earlier proposed in U.S. Pat. No. 5,041,522. However, none of the polymers described therein was derived from the heterocyclic monomer tetraaminopyridine. Also in view of the poor results obtained when preparing a polymer based on tetraaminopyridine and terephthalic acid, it should be considered extremely surprising that it is not only possible to obtain a polymer of high molecular weight from tetraminopyridine and 2,5-dihydroxyterephthalic acid, but also that, to all appearances, it is possible to spin fibres therefrom which have interesting properties and differ favourably from fibres made of the structurally related obtained from 2,5-dimercapto-p-phenylene diamine and 2,5-dihydroxyterephthalic acid, the preparation of which is disclosed in U.S. Pat. No. 5,041,522.
At least 50% of the rigid rod polymers according to the present invention is composed of recurring groups of pyridobisimidazole-2,6- diyl(2,5-dihydroxy-p-phenylene), while in the remaining groups the 2,5-dihydroxy-p-phenylene is replaced by an arylene which may be substituted or not and/or the pyridobisimidazole is replaced by benzobisimidazole, benzobisthiazole, benzobisoxazole, pyridobisthiazole, and/or pyridobisoxazole. Preference is given in that case to ladder polymers at least 75% of the recurring groups of which is made up of pyridobisimidazole-2,6-diyl(2,5-dihydroxy-p-phenylene), while in the remaining groups the 2,5-dihydroxy-p-phenylene is replaced by an arylene which may be substituted or not and/or the pyridobisimidazole is replaced by benzobisimidazole, benzobisthiazole, benzobisoxazole, pyridobisthiazole, and/or pyridobisoxazole.
In the case of partial replacement (up to 50% at most) of the 2,5-dihydroxy-p-phenylene, preference is given to a compound which is left after removal of the carboxyl groups of an arylene dicarboxylic acid such as isophthalic acid, terephthalic acid, 2,5-pyridine dicarboxylic acid, 2,6-naphthalene dicarboxylic acid, 4,4'-diphenyl dicarboxylic acid, 2,6-quinoline dicarboxylic acid, and 2,6-bis(4-carboxyphenyl)pyridobisimidazole.
In this document, the relative viscosity .eta..sub.rel is measured on a solution with a concentration of 0.25 g/dl in methane sulphonic acid at 25.degree. C., unless indicated otherwise.
If the making of one- or two-dimensional objects, such as fibres, films, tapes, and the like, is desired, the polymer of the present invention should have a relative viscosity .eta..sub.rel of at least 3.5. Preferably, the relative viscosity .eta..sub.rel is at least 5, more particularly, equal to or higher than about 10. So far, optimum results have been attained using the homopolymer .eta..sub.rel >10. When spinning fibres from the homopolymer, very good results are obtained if .eta..sub.rel is highe
REFERENCES:
patent: 4002679 (1977-01-01), Arnold
patent: 4079039 (1978-03-01), Gerber
patent: 4533692 (1985-08-01), Wolfe et al.
patent: 5039778 (1991-08-01), Dang et al.
patent: 5041522 (1991-08-01), Dang et al.
patent: 5136012 (1992-08-01), Dang et al.
Lyotropic Main Chain Liquid Crystal Polymers; Advances in Polymer Science 98; M.G. Northolt and D.J. Sikkema, pp. 115-177.
Encyclopedia of Polymer Science and Engineering, vol. 11, Peroxy Compounds to Polyesters; John Wiley & Sons, 1985, pp. 601-635.
Journal of Polymer Science, 1973 by John Wiley & Sons, Inc., pp. 1703-1719.
X-Ray Defraction Methods in Polymer Science, Leroy E. Alexander, pp. 198-259.
The Plastics and Rubber Institute Seventh Int'l. Conf. on Deformation, Yield and Fracture of Polymers at Cambridge (UK 1988), pp. 11/1-11/4.
British Corrosion Journal; F.N. Smith and H. Van Droffelaar; 1991; vol. 26; No. 4; pp. 265-267.
Lishinsky Vadim Leonidovich
Sikkema Doetze Jakob
Akzo Nobel nv
Morris Louis A.
Noto Joseph M.
Seidleck James J.
Truong Duc
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