Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – From sulfur-containing reactant
Patent
1990-07-11
1992-10-06
Anderson, Harold D.
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
From sulfur-containing reactant
528374, C08G 7504, C08G 7514
Patent
active
051533057
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention relates to a process for preparing a polyarylene thioether, more particularly to a process for preparing a polyarylene thioether such as polyphenylene thioether under mild polymerization conditions with a simple and easy procedure at a low cost.
BACKGROUND ART
Polyarylene thioethers including polyphenylene thioether have heretofore been prepared by condensation polymerization of an aromatic dihalide and an alkali metal sulfide in a polar solvent at a high temperature under pressure.
This condensation polymerization has, however, such problems that (i) an alkali metal salt remains in polyarylene thioether and deteriorates its electrical properties and (ii) this production cost is high because a great amount of energy is consumed due to carrying out polymerization at a high temperature under pressure.
A process in which thiophenol monomer is polymerized in the presence of a catalyst such as MoCl.sub.5 /CF.sub.3 COOH is disclosed in USSR Patent No. 698,988. However, the product resulting from that process is poly(arylene thiol), and the process is not advantageous in industrial use since the catalyst used is expensive.
Furthermore, another process using sulfuric acid as a catalyst is known, but said process has such a disadvantage that much by-products and a considerable amount of cross-linked polymers are produced.
Processes for preparing polyarylene thioethers using diphenyldisulfide and/or thiophenol have been disclosed also in Japanese Patent Application Laid-Open Nos. 213526/1988 and 213527/1988, but they have the problems that expensive Lewis acids and oxidizing agents must be used in large amounts.
The present invention was accomplished under above circumstances, and the object of it is to dissolve the problems mentioned above, and to provide a process, which is greatly advantageous in industrial use, for producing a polyarylene thioether having excellent electric, mechanical and chemical properties, particularly a substantially straight-chain polyarylene thioether with little by-production of cross-linked polymers, with a simple and easy procedure, under mild polymerization conditions, and at a low cost.
DISCLOSURE OF THE INVENTION
The present inventors have earnestly investigated so as to overcome the problems mentioned above. As the result, it was found that the above object could be attained by using diaryl disulfides or thiophenols as the reaction material, and polymerizing them with oxygen in the presence of catalyst. The present invention has been completed based on such findings.
That is, the present invention provides a process for preparing a polyarylene thioether (or a polyarylene sulfide), which comprises oxidation coupling polymerization, with oxygen, of at least one compound selected from the group consisting of diaryl disulfides represented by the general formula (I): ##STR2## (wherein S indicates a sulfur atom, R.sup.1 to R.sup.8 are each a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a halogen atom, or an alkoxyl group having 1 to 10 carbon atoms, and R.sup.1 to R.sup.8 may be different from or indentical with each other) and thiophenols (or arylthiols) represented by the general formula (II): ##STR3## (wherein R.sup.9 to R.sup.12 are each a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, a halogen atom or a alkoxyl group having 1 to 10 carbon atoms, and R.sup.9 to R.sup.12 may be different from or identical with each other), with the use of catalyst, in the presence of an acid.
BEST MODE FOR CARRYING OUT THE INVENTION
R.sup.1 to R.sup.12 in the abovementioned general formulae (I) and (II) will be explained in detail as follows.
Specific examples of R.sup.1 to R.sup.12 to are hydrogen atom; alkyl groups having 1 to 10 carbon atoms such as methyl group, ethyl group, propyl group, 1-methylethyl group, butyl group, 1-methylpropyl group, 2-methylpropyl group, 1,1-dimethylethyl group, pentyl group, hexyl group, heptyl group and octyl group; halogen atom such as fluorine atom, chlorine atom, bromine atom and iodine atom
Jikei Mitsutoshi
Nishide Hiroyuki
Tsuchida Eishun
Yamamoto Kimihisa
Anderson Harold D.
Idemitsu Petrochemical Co. Ltd.
Research Institute for Production Development
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