Aminocarbonate compounds and their use as catalysts

Details Aminocarbonate compounds and their use as catalysts Aminocarbonate compounds and their use as catalysts

1994-08-11

1997-11-11

Cintins, Marianne M.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbonate esters

C07C 6996

Patent

active

056866437

DESCRIPTION:

BRIEF SUMMARY
FIELD OF THE INVENTION

The present invention relates to aminocarbonate compounds and their use as catalysts for the production of urethane polymers and/or urea polymers.


BACKGROUND OF THE INVENTION

Catalysts for the production of polyurethanes are known (see J. H. Saunders and K. C. Frisch, Polyurethanes Chemistry and Technology, 1962, p. 73 ff.). Said catalysts are organic, organometallic and inorganic compounds. From the group of organic compounds particularly tertiary amines, e.g. bis(dimethylaminoethyl)ether (U.S. Pat. No. 3,400,157), aminoorthoester (U.S. Pat. No. 3,786,029) and .beta.,.beta.'-dimorpholinodiethylester (DE 2 138 403) are used. Examples for metal Catalysts are Sn(II)/Sn(IV) salts or Fe(III) salts (DE 3 938 203 A1).
However, the catalysts used at present have many disadvantages. A great number of amines, e.g. bis(dimethylaminoethyl)ester, have a very unpleasant odor which is disadvantageous both during the production of polyurethanes and in the processing of polyurethane materials produced with the aforesaid catalysts. Furthermore, it has hitherto been impossible to definitely infer the odor and the properties as catalysts for the production of polyurethanes from the chemical structure of a compound.
Another criterion for the classification of a catalyst is the equilibrium between its activity and the isocyanate-alcohol reaction and the isocyanate-water reaction. When comparing amine catalysts of similar chemical structures, e.g. bis(dimethylaminoethyl)ether and dimethylaminopropyldimethylaminoethylether, an extension by only one methylene group will result in a significant drop in activity and, above all, in a considerable shift in the catalytic impact on the isocyanate-water reaction toward the isocyanate-alcohol reaction. A catalyst having a strong blowing activity will thus degenerate into a medium-active gelling catalyst (see N. Malwitz et el., Proceedings of the 30th Annual Polyurethane Technical/Marketing Conference, Oct. 15-17, 1986, p. 338-353).
Therefore, in order to reduce the odor of amine catalysts, amine compounds having high molecular weights and, incidental thereto, low vapor pressures have been used. However, since such compounds present low mobilities and, thus, low activities, great quantities are required for production.
Moreover, according to the prior art, the odor is reduced by using amino catalysts with substituents having isocyanate-reactive hydrogen atoms. Examples for such catalysts are dimethylethanolamine and dimethylaminopropylamine. In JP-A-59 191 743 the products obtained by reaction of polyamine with carbonates as polyurethane catalysts have been described. A great disadvantage of the prior art is that the amino catalysts remain in the polyurethane which, as is generally known, may catalyze the back reaction of the urethane groups or urea groups and would deteriorate the hydrolysis and ageing resistance.
Therefore, it was the object of the present invention to provide novel compounds which are suitable as catalysts for the production of polyurethanes and/or polyureas while avoiding or reducing the aforementioned disadvantages.


SUMMARY OF THE INVENTION

In accordance with the present invention the problem is solved by providing aminocarbonate compounds corresponding to the following general formula (I) ##STR1## wherein R.sup.1 and R.sup.2 are equal or different and R.sup.1 comprises a tertiary amino group and also R.sup.2 comprises a tertiary amino group, or constitutes methyl, a branched or unbranched alkyl group of 2 to 20 carbon atoms, phenyl or an alkyl-substituted phenyl group of up to 20 carbon atoms and, preferably, alkyl of 1 to 3 carbon atoms or phenyl.
R.sup.1 and R.sup.2, if also R.sup.2 comprises a tertiary amino group, is (are) preferably a group corresponding to the following general formula (II) ##STR2## wherein Z.sup.1 and Z.sup.2 are equal or different and each constitutes methyl or a branched or unbranched alkyl group of 2 to 6 carbon atoms or together form a morpholine o group or a piperazine group corresponding to the following ge

REFERENCES:
patent: 4737518 (1988-04-01), Nomura et al.
Zinner, G., "Organic Derivatives of Peroxycarbonic Acids and Peroxysulfurous acids" of Angew. Chem. 69, 480(1957), Abstract.
Abstract to EP 104984 A2, Olofson et al., 1984.

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