Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – From organic oxygen-containing reactant
Patent
1993-06-21
1995-04-04
Foelak, Morton
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
From organic oxygen-containing reactant
C08G 6534
Patent
active
054039126
DESCRIPTION:
BRIEF SUMMARY
This invention relates to a process for the manufacture of poly(alkylene oxide) oligomers and co-oligomers, and low molecular weight polymers and copolymers. More specifically, the present invention relates to a process for the production of such compounds by intermolecular dehydration of polyhydroxy compounds in the presence of perfluorinated resin sulfonic acid catalysts.
The term poly(alkylene oxides) is used herein to refer to the reaction product produced by the process of the invention described. The scope of this term should be considered in light of the spirit of the following description and should not be considered limited to the specific examples.
Poly(alkylene oxides) are important precursors in the preparation of copolymers and segmented copolymers such as polyurethane and polyurethaneurea elastomers. These poly(alkylene oxides) when incorporated into polyurethanes form the "soft segment", and impart many useful properties to the polyurethane including elasticity, hydrolytic stability, thermal stability, and abrasion resistance. Common poly(alkylene oxides) that are produced for such purposes include poly(ethylene oxide), poly(propylene ozide) and poly(tetramethyleneoxide). These compounds may be prepared by the ring-opening polymerization of the corresponding cyclic ethers. This method is most suitable to polymerize cyclic ethers having 2-4 carbon and 1-3 oxygen atoms in the ring. Larger compounds however may also be used. For example, a cyclic ether having more than 4 carbon atoms and one hetero atom in a ring that undergoes ring opening polymerization is oxacycloheptane. German Patent Specification No. 1,125,386 describes a process to prepare poly(hexamethylene oxide) from oxacycloheptane using Friedel-Crafts catalysts or Lewis Acids.
German Patent Specification No. 1,156,709 describes a process for preparing poly(alkylene oxides) from alkanediols having 5-12 carbon atoms by heating to temperatures in the range from 200.degree. to 400.degree. C. in the presence of solid, non-basic catalysts such as oxides of aluminum, tungsten and chromium etc. One major disadvantage of this process is the need to use such high temperatures. The use of high temperatures may lead to the formation of undesirable side products and to discoloration of the product. Poly(alkylene oxides) having molecular weights of 450 to 1400 may be obtained by this process in yields ranging from 18-55%.
An article in Journal of the American Chemical Society, Vol. 72, pp 2216-2219 (1949) by P. J. Flory and M. J. Rhoad, describes a process to prepare poly(decamethylene oxide) by sulphuric acid catalysed polymerization of 1,10-decanediol at 200.degree. C. However, purification of the product to remove the acid catalyst in this process is difficult. The acid catalyst is usually removed either by repeated recrystallization or by treatment with a base such as calcium hydroxide followed by washing the product with water. Often emulsions are formed during the washing step making isolation of the product extremely difficult. Incomplete removal of the acid catalyst can cause degradation of the poly(alkylene oxide). Furthermore, significant charring occurs especially when long reaction times are used.
It is an object of the present invention to overcome, or at least alleviate one or more of the difficulties associated with the prior art.
The present invention provides a process for the production of a poly(alkylene oxide) which includes, providing a polyhydroxy compound or compounds and an acid resin catalyst or a salt thereof that has been converted to the acid form; and
reacting said polyhydroxy compound or compounds in the presence of said acid resin catalyst at a temperature and under conditions to allow polymerization. Preferably the catalyst is a sulfonic acid resin containing one or more halogen atoms. More preferably, the halogen atoms are fluorine. Most preferably, the sulfonic acid resin is a perfluorinated sulfonic acid resin.
A preferred catalyst used in the process of the invention is a polymer of an ethylenically unsaturated
REFERENCES:
patent: 2243481 (1941-05-01), Meiler
patent: 3120497 (1964-02-01), Bungs
patent: 3126356 (1964-03-01), Kraft
patent: 3188353 (1965-06-01), Holtschmidt
patent: 4661411 (1987-04-01), Martin et al.
Exhibit A-Supplementary European Search Report.
Exhibit B-German 24 14 647-claims in English.
Abstract page of EP 0 235 998 A2 and A3.
Abstract page of EP 0 106 903.
PCT International Preliminary Examination Report.
PCT International search Report.
Gunatillake Pathiraja A.
Meijs Gordon F.
Rizzardo Ezio
Commonwealth Scientific and Industrial Research Organization
Foelak Morton
Mosley Terressa
Unisearch Limited
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