Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Patent
1997-08-26
1999-08-17
Krass, Frederick
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
568617, 525539, 525412, 528392, 528405, 528417, C08G 6520
Patent
active
059395907
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to tetrahydrofuran/but-2-yne-1,4-diol copolymers containing C--C triple bonds and having an average molecular weight M.sub.n of from 500 to 3500 Dalton and a content of from 0.5 to 3.0 mol of triple bonds/mol of copolymer and blends of these copolymers with polytetrahydrofuran having an average molecular weight M.sub.n of from 500 to 3500 Dalton.
The present invention further relates to a process for the preparation of tetrahydrofuran/but-2-yne-1,4-diol copolymers containing C--C triple bonds.
The present invention also relates to a process for the preparation of polyoxytetramethylene glcyol (polytetrahydrofuran, PTHF) and a process for the preparation of polyoxytetramethylene glycols containing C--C double bonds, polyoxytetramethylene glycols containing internal C--C double bonds and having an average molecular weight M.sub.n of from 500 to 3500 Dalton and a content of from 0.1 to 3 mol of double bonds/mol of polyoxytetramethylene glycol and blends of these polyoxytetramethylene glycols containing internal C--C double bonds with polytetrahydrofuran having an average molecular weight M.sub.n of from 500 to 3500 Dalton.
It is known that tetrahydrofuran can be polymerized with saturated .alpha., .omega.-diols and hydrated heteropolyacids as catalysts to give saturated polyether polyols. According to U.S. Pat. No. 4,658,065 (Aoshima et al.), polyoxytetramethylene glycol is obtained, for example, in continuous experiments for the polymerization of tetrahydrofuran in the presence of 1,4-butanediol using hydrated dodecatungstatophosphoric acid as a catalyst. This process has the disadvantage that only unsatisfactory space-time yields are obtained in the preparation of polytetrahydrofuran having a relatively low average molecular weight, for example from polytetrahydrofuran having an average molecular weight of 1000 Dalton. This disadvantage is particularly serious because polytetrahydrofuran having this relatively low average molecular weight is of particularly great commercial interest.
According to EP-A 503 393, polyoxytetramethylene glycol monoethers are prepared from monohydric alcohols by polymerization of tetrahydrofuran in the presence of a monohydric alcohol using an anhydrous heteropolyacid catalyst.
According to Maksimov et al., Polymer Science, Ser. B. 36 (1994), 412, the monopropargyl ether of tetrahydrofuran is obtained by the polymerization of tetrahydrofuran with propargyl alcohol in the presence of anhydrous tungstatophosphoric acid but, owing to its chemical structure, is of virtually no industrial use.
According to EP-A 126 471, hydrated heteropolyacids are used as catalysts for the polymerization of tetrahydrofuran (THF) to give polyoxytetramethylene glycol. The disadvantage of this process is in particular the low THF conversion, which has only about 8% in the preparation of polyoxytetramethylene glycols having a relatively low average molecular weight, which are of particular commercial interest. The polyoxytetramethylene glycols prepared by this process are worthy of further improvement with respect to their color number.
It is an object of the present invention to provide novel polyoxyalkylene glycols which contain C--C triple bonds or C--C double bonds, where these unsaturated groups should be located at the end and/or in the interior of the polyoxyalkylene glycol molecules. An associated object is to provide a process for the preparation of such polyoxyalkylene derivatives. Starting from these unsaturated polyoxyalkylene glycol derivatives, it is furthermore intended to provide a process for the preparation of polyoxytetramethylene glycol, also referred to as polytetrahydrofuran (PTHF). The object is to obtain polytetrahydrofuran having a particularly low color number and high uniformity.
We have found that this object is achieved by tetrahydrofuran/but-2-yne-1,4-diol copolymers containing C--C triple bonds and having an average molecular weight M.sub.n of from 500 to 3500 Dalton and a content of from 0.5 to 3.0 mol of triple bonds/mol of copolymer and blend
REFERENCES:
patent: 4658065 (1987-04-01), Aoshima et al.
patent: 5393847 (1995-02-01), Alloin et al.
patent: 5395959 (1995-03-01), Weyer et al.
Copy of German Language OZ 0050/42293.
Derwent 70-29238.
Macromolecules, No. 8, (1986).
J. of Appl. Polymer Sci, May 20, No. 7, (1988).
TetrahydrofuranPolymerization . . . , Poly. Sci, vol. 36.
Becker Rainer
Fischer Rolf
Groll Peter
Heilen Gerd
Palm Christof
BASF - Aktiengesellschaft
Krass Frederick
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