Catalyst – solid sorbent – or support therefor: product or process – Catalyst or precursor therefor – Organic compound containing
Reexamination Certificate
2000-10-10
2003-07-22
Seidleck, James J. (Department: 1711)
Catalyst, solid sorbent, or support therefor: product or process
Catalyst or precursor therefor
Organic compound containing
C252S182240, C252S182260, C528S053000, C528S076000, C528S085000, C521S115000, C521S116000, C521S118000, C521S129000
Reexamination Certificate
active
06596663
ABSTRACT:
The present invention relates to a catalyst composition for the production of a polyurethane resin of soft, hard, semihard or elastomer type, and a method for producing a polyurethane resin employing such a catalyst composition. More particularly, it relates to a catalyst composition for the production of a polyurethane resin, which does not substantially discharge a volatile amine type catalyst, and a method for producing such a polyurethane resin.
A polyurethane resin is produced by reacting a polyol with an organic polyisocyanate in the presence of a catalyst and, if necessary, a blowing agent, a surfactant, a cross-linking agent, etc. Heretofore, it has been known to employ various metal compounds or tertiary amine compounds as catalysts for the production of such polyurethane resins. These catalysts are industrially used alone or in combination.
The tertiary amine compounds are particularly excellent in the productivity and the moldability and thus widely used as tertiary amine catalysts for the production of polyurethane resins. They include, for example, conventional compounds such as triethylenediamine, N,N,N′,N′-tetramethyl-1,6-hexanediamine, bis(2-dimethylaminoethyl)ether, N,N,N′,N″,N″-pentamethyldiethylenetriamine, N-methylmorpholine, N-ethylmorpholine and N,N-dimethylethanolamine. Metal catalysts tend to be poor in the productivity and moldability, and in most cases, they are used in combination with tertiary amine catalysts, and they are rarely employed alone.
However, the above-mentioned tertiary amine catalysts will remain in a free form in the polyurethane resin products and will gradually be discharged as volatile amines, whereby various problems will be brought about. For example, a volatile amine discharged from a polyurethane foam product in the interior of an automobile creates an odor problem. Further, in recent years, there has been a so-called fogging problem, such that a volatile component in a polyurethane foam will deposit on a window glass of an automobile thereby to bring about fogging of the window glass and thereby to reduce the commercial value. In addition to such problems, there is a pollution problem such that a volatile amine discharged from such a polyurethane product will pollute other materials.
As a method for solving such problems, it has been proposed to employ an amine catalyst having in its molecule, primary and secondary amino groups or a hydroxy alkyl group which is capable of reacting with an organic polyisocyanate (JP-B-57-14762, JP-B-61-31727), to employ a carbonate of a primary amine (JP-A-59-191743) or to employ an amine catalyst having a hydroxyl group and a carbonate of a primary amine in combination (JP-A-4-65416). It is said that by these methods, the above-mentioned problems can be avoided, since the amine catalyst employed will be fixed in the polyurethane resin skeletal structure in the form as reacted with an organic polyisocyanate.
However, even if such an amine catalyst having a reactive group, is employed, the above problems cannot be solved completely. An amine catalyst having a reactive group usually has a drawback that the catalytic activity gradually decreases, as it is reacted with an organic polyisocyanate in the process for forming a polyurethane and will be fixed in the polyurethane resin. Particularly, an amine catalyst having primary and secondary amino groups, tends to start reacting with an organic polyisocyanate from the initial stage in the process for forming a polyurethane and will be fixed in the polyurethane resin, whereby the decrease of the catalytic activity will be substantial, and curing of the polyurethane resin tends to be inadequate, thereby to bring about a decrease in the productivity. Whereas, by the method of employing a carbonate of a primary amine as the catalyst, the curing deficiency of the resin may be overcome by the block effects of the carbonate, but the catalyst is required to be used in a large amount, and further, a volatile amine is likely to be discharged, probably because the fixing in the polyurethane resin is insufficient.
Further, among these amine catalysts having reactive groups, there are some which may be once fixed in the polyurethane resin skeletons as reacted with organic polyisocyanates, but will be discharged as free amine catalysts when the polyurethane products are brought to a high temperature to bring the decomposition of bonds. Further, another drawback of the amine catalysts having such reactive groups is that the mechanical properties of the resulting polyurethane products are likely to deteriorate.
Metal catalysts other than the amine catalysts, such as organic tin compounds, will not bring about the above problems, but by their single use, the productivity, the physical properties and the moldability tend to be poor, and further, an environmental problem due to tin has been pointed out.
The present invention has been made in view of the above problems, and its object is to provide a production method whereby a polyurethane resin which is free from generation of a volatile amine and which undergoes no substantial deterioration of the physical properties, can be obtained with good productivity and moldability, and a catalyst composition to be used for the method.
The present inventors have conducted an extensive study to solve the above problems. As a result, they have found that by using an amine compound containing at least one amino group and at least one tertiary amino group in its molecule and a tertiary amine compound having at least two hydroxyalkyl groups in its molecule in combination, it is possible to obtain a polyurethane resin which is substantially free from a volatile amine, without no substantial deterioration of the physical properties and with good moldability and productivity. The present invention has been accomplished on the basis of this discovery.
Namely, the present invention provides a catalyst composition for the production of a polyurethane resin, which comprises an amine compound of the following formula (1):
wherein each of R1 and R2 which are independent of each other, is a C
1-4
alkyl group, such alkyl groups bonded to each other directly or via a nitrogen atom or an oxygen atom to form a ring structure, a dimethylaminopropyl group or a diethylaminopropyl group, and R3 is a C
2-16
straight chain or branched chain alkylene group, and an amine compound of the following formula (2):
wherein each of R4 and R5 which are independent of each other, is a C
1-4
alkyl group, such alkyl groups bonded to each other directly or via a nitrogen atom or an oxygen atom to form a ring structure, a dimethylaminopropyl group or a diethylaminopropyl group, R6 is a C
2-16
straight chain or branched chain alkylene group, R7 is a C
2-3
straight chain or branched chain alkylene group, and n is an integer of from 0 to 2, and a method for producing a polyurethane resin, wherein such a catalyst composition is employed.
Now, the present invention will be described in detail with reference to the preferred embodiments.
The catalyst composition for the production of a polyurethane resin of the present invention comprises an amine compound of the above formula (1) and an amine compound of the above formula (2).
The amine compound of the above formula (1) is one having at least one amino group and at least one tertiary amino group in its molecule. Specifically, it includes, for example, N,N-dimethylethylenediamine, N,N-dimethylpropanediamine, N,N-dimethylbutanediamine, N,N-dimethylpentanediamine, N,N-dimethylneopentanediamine, N,N-dimethylhexanediamine, N,N-dimethylhexadecyldiamine, N,N-diethylethylenediamine, N,N-diethylpropanediamine, 4-amino-1-diethylaminopentane, N,N-diethylhexanediamine, N-(aminoethyl)piperidine, N-(aminoethyl)-N′-methylpiperazine, N-(aminoethyl)morpholine, N-(aminopropyl)piperidine, N-(aminopropyl)-N′-methylpiperazine, N-(aminopropyl)morpholine, N,N-bis(dimethylaminopropyl)ethylenediamine, N,N-bis(dimethylaminopropyl)propanediamine, and N,N-bis(diethylaminopropyl)propanediamine. Among
Ishida Masaki
Kometani Hiroyuki
Tamano Yutaka
Bissett Melanie
Nixon & Vanderhye
Seidleck James J.
Tosoh Corporation
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