Catalyst compositions for the production of polyurethanes

Details Catalyst compositions for the production of polyurethanes Catalyst compositions for the production of polyurethanes

1999-03-26

2001-11-06

Sergent, Rabon (Department: 1711)

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

Organic compounds

Amino nitrogen containing

C502S167000, C502S200000, C564S188000, C564S191000, C564S193000, C564S197000, C564S198000, C546S133000, C546S137000, C546S184000, C546S242000, C546S248000

Reexamination Certificate

active

06313346

ABSTRACT:

CROSS-REFERENCE TO RELATED APPLICATIONS
Not applicable.
STATEMENT REGARDING FEDERALLY SPONSORED RESEARCH OR DEVELOPMENT
Not applicable.
BACKGROUND OF THE INVENTION
Polyurethanes are useful in a variety of applications. For example, polyurethane elastomers are used in automotive parts, shoe soles, and other products in which toughness, flexibility, strength, abrasion resistance, and shock-absorbing properties are required. Polyurethanes are also used in coatings and in flexible and rigid foams.
Polyurethanes, in general, are produced by the reaction of a polyisocyanate and a polyol in the presence of a catalyst. The catalyst is typically a low molecular weight tertiary amine such as triethylenediamine.
Polyurethane foams are produced through the reaction of a polyisocyanate with a polyol in the presence of various additives. One class of additives which is particularly effective as blowing agents is the chlorofluorocarbons (CFCs). CFCs vaporize as a result of the reaction exotherm during polymerization and cause the polymerizing mass to form a foam. However, the discovery that CFCs deplete ozone in the stratosphere has resulted in mandates for restricting CFC use. Therefore, more efforts have gone into the development of alternatives to CFCs for forming urethane foams and water blowing has emerged as an important altemative. In this method, blowing occurs from carbon dioxide generated by the reaction of water with the polyisocyanate. Foams can be formed by a one-shot method or by formation of a prepolymer and subsequent reaction of the prepolymer with water in the presence of a catalyst to form the foam. Regardless of the method, a balance is needed between reaction of the isocyanate and the polyol (gelling) and the reaction of the isocyanate with water (blowing) in order to produce a polyurethane foam in which the cells are relatively uniform and the foam has specific properties depending on the anticipated application; for example, rigid foams, semi-rigid foams, and flexible foams.
The ability of the catalyst to selectively promote either blowing or gelling is an important consideration in selecting a catalyst for the production of a polyurethane foam with specific properties. If a catalyst promotes the blowing reaction to too high a degree, carbon dioxide will be evolved before sufficient reaction of isocyanate with polyol has occurred. The carbon dioxide will bubble out of the formulation, resulting in collapse of the foam and production of a poor quality foam. At the opposite extreme, if a catalyst promotes the gelling reaction too strongly, a substantial portion of the carbon dioxide will be evolved after a significant degree of polymerization has occurred. Again, a poor quality foam is produced; characterized by high density, broken or poorly defined cells, or other undesirable features. Frequently, a gelling catalyst and a blowing catalyst are used together to achieve the desired balance of gelling and blowing in the foam.
Tertiary amine catalysts have been used to in the production of polyurethanes. The tertiary amine catalysts accelerate both blowing (reaction of water with isocyanate to generate carbon dioxide) and gelling (reaction of polyol with isocyanate) and have been shown to be effective in balancing the blowing and gelling reactions to produce a desirable product. However, typical tertiary amines used as catalysts for polyurethane production generally have offensive odors and many are highly volatile due to low molecular weight. Release of tertiary amines during polyurethane production may present significant safety and toxicity problems, and release of residual amines from consumer products is generally undesirable.
Various alternatives to low molecular weight tertiary amine catalysts have been reported in the prior art. Examples are described below:
U.S. Pat. No. 3,073,787 (Krakler, 1963) discloses an improved process for preparing isocyanate foams in which a 3-dialkylaminopropionamide and 2-dialkylaminoacetamide are used as catalysts.
U.S. Pat. No. 4,007,140 (Ibbotson, 1977) discloses the use of various tertiary amines such as N,N′-bis(3-dimethylaminopropylamino)urea as low odor catalysts for the manufacture of polyurethanes.
U.S. Pat. No. 4,094,827 (McEntire, 1978) discloses the use of certain alkyl substituted ureas, such as N,N-bis(dimethylaminopropyl)urea, as catalysts in the production of polyurethane foam.
U.S. Pat. No. 4,194,069 (Speranza et al., 1980) discloses the use of N-(3-dimethylaminopropyl)-N′-(3-morpholinopropyl)urea as a catalyst for producing polyurethanes.
U.S. Pat. No. 4,248,930 (Haas et al., 1981) discloses new tertiary amine compounds, such as bis(dimethylamino-n-propyl)amine, as catalysts for the production of cellular or non-cellular polyurethane resins.
U.S. Pat. No. 4,644,017 (Haas et al., 1987) discloses the use of diffusion stable amino alkyl ureas having tertiary amino groups in the production of a polyisocyanate addition product.
DE 3027796 (1982) (Derwent abstract 82-13914E) discloses the use of dialkyl aminoalkyl urea catalysts for the production of polyurethane foam. It is reported that no smell is generated at polyurethane preparation temperatures.
EP 799,821 (1997) discloses aminelamide catalysts, such as 3-[3-dimethylaminopropyl]amino-N,N-dimethylpropanamide and 3-[3-dimethylaminopropyl]amino-N-[3-dimethylaminopropyl]propanamide, for the formation of polyurethanes. The catalysts have low fugitivity due to their reactivity with isocyanates.
U.S. 5,824,711 (Kimock et al., 1998) discloses N,N,N′-trimethylbis(aminoethyl)ether substituted urea compositions for the production of polyurethanes.
U.S. 5,874,483 (Savoca et al., 1999) discloses aminopropylbis(aminoethyl)ether compositions for the production of polyurethanes.
BRIEF SUMMARY OF THE INVENTION
The present invention is directed to new compositions which are useful for catalyzing the reaction between an organic polyisocyanate and a compound containing a reactive hydrogen to form polyurethanes. The compositions have been found to be especially effective catalysts for the blowing reaction, in which an organic polyisocyanate reacts with water, and the gelling reaction, in which an organic polyisocyanate reacts with a polyol. The catalyst composition is represented by the formula below:
wherein R is a linear alkyl, branched alkyl, cycloalkyl, polycyclic alkyl, alkylaminoalkyl, or alkyloxyalkyl group having 1 to about 20 carbon atoms and at least one primary, secondary, or tertiary amino functional group, preferably a tertiary amino group. The invention is also directed to a process for producing polyurethanes using the new catalyst composition.
These novel catalysts are shown to have unexpectedly high activity and good blowing or gelling selectivity, depending upon the structure. The presence of an amide group in the compounds causes the catalysts to be bound to the urethane during the reaction and thus they are not released from the finished product. The above properties make these materials useful for the production of polyurethanes, especially polyurethane foams.
DETAILED DESCRIPTION OF THE INVENTION
The compounds of formula I are prepared by the nucleophilic addition of hydroxyl functional amine to an acrylamide. Hydroxyl functional amine and acrylamide are present in the reaction mixture in molar ratio of from about 1:10 to about 20:1, and preferably at a ratio of 1 to 2 moles hydroxyl functional amine per equivalent of acrylamide. Air is used to saturate the reaction mixture in order to inhibit the free radical polymerization of acrylamide. The reaction is preferably carried out at atmospheric pressure.
The reaction is conducted in the presence of base catalysts such as alkali or alkaline earth metal hydrides, hydroxides, or alkoxides. Other useful catalysts include aryl- and alkyl-lithium, potassium and sodium, tertiary amines, and metal amides. The catalyst is present in the reaction mixture in an amount between about 0.00005 and about 5 wt. %, and preferably between 0.0005 and 0.001 wt. %. of the total weight of the r

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