US3821131A
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US
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Beta-amino carbonyl catalysts for polyurethane preparation
Assignee: Union Carbide Corp
•
Filing: 1972-11-27
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Granted: 1974-06-28
•
Expires: 1992-11-27
Abstract
Abstract Provided as catalysts for the formation of cellular urethane polymers ranging from flexible to rigid foams, are beta-amino carbonyl compounds wherein carbonyl is present as an amido or carboxylic acid ester group and the beta-amino group is present as dialkylamino or an N-morpholino or N,N''-piperazino heterocyclic nucleus. Effective in the catalysis of the waterisocyanate reaction, these beta-amino amides and beta-amino esters are used with particular advantage in the manufacture of water-blown flexible foams, both molded and free-rise, including high-resilience and flame-retarded foam. The beta-amino carbonyl catalysts allow for the formation of foam products essentially free of the odor associated with amines such as Nethylmorpholine. In view of this highly desirable characteristic and their other beneficial properties, the catalysts of the invention are advantageously employed as direct replacements for N-ethylmorpholine in high-resilience and other foam formulations.
Inventors
- 👤 D Priest
- 👤 M Sandner
- 👤 D Trecker
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 17:53
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/08; C08G18/16; C08G18/18; C08G18/1841
Claims Analysis
Total Claims: 39
Claim 1
Independent Claim
14 words
The method of claim 1 in which said alkyl beta-(dialkyl amino)carboxylate is ethyl 3-(N,N-dimethylamino)propionate.
Claim 2
Independent Claim
40 words
A method for producing a urethane polymer which comprises reacting an organic polyisocyanate and an organic polyol having an average of at least two hydroxyl groups per molecule, in the presence of a 2-(N,N-dialkylamino)ethyl 3-(N'', N'' -dialkylamino)carboxylate having the formula:
Claim 3
Dependent Claim
14 words
The method of claim 3 in which said 2-(N,N-dialkylamino)ethyl 3-(N'', N''-dialkylamino)carboxylate is 2-(N,N-dimethylamino)ethyl 3-(N'',N''-dimethlamino)propionate.
Claim 4
Independent Claim
49 words
A method for producing a polyurethane foam which comprises reacting an organic polyisocyanate and an organic polyol reactant comprising a polyether polyol having an average of at least two hydroxyl groups per molecule, in the presence of a blowing agent and a catalyst comprising a 3-dialkylamino-N,N-dimethylamide having the formula:
Claim 5
Dependent Claim
11 words
The method of claim 5 in which said 3-dialkylamino-N,N-dimethylamide is 3-dimethylamino-N,N-dimethylpropionamide.
Claim 6
Dependent Claim
23 words
The method of claim 5 in which the lower alkyl groups represented by R1 and R2 of said 3-dialkylamino-N,N-dimethylamide are other than methyl.
Claim 7
Dependent Claim
16 words
The method of claim 5 in which R3 of said 3-dialkylamino-N,N-dimethylamide is a lower alkyl group.
Claim 8
Independent Claim
39 words
A method for producing a urethane polymer which comprises reacting an organic polyisocyanate and an organic polyol having an average of at least two hydroxyl groups per molecule, in the presence of a beta-amino carbonyl compound having the formula,
Claim 9
Dependent Claim
70 words
A process for producing flexible polyurethane foam which comprises simultaneously reacting and foaming a reaction mixture containing: (a) an organic polyisocyanate; (b) an organic polyol reactant comprising a polyether polyol having an average hydroxyl functionality of from 2.1 to about 4 and a hydroxyl number from about 20 to about 100; (c) water as a source of blowing action; and (d) an amine catalyst comprising a 3-dialkylamino-N,N-dimethylamide having the formula,
Claim 10
Dependent Claim
38 words
The method of claim 10 in which said organic polyol comprises a mixture of said polyether polyol and a polymer/polyol produced by the in situ polymerization of at least one polymerizable ethylenically unsaturated monomer in a polyether polyol.
Claim 11
Dependent Claim
20 words
The method of claim 10 in which the isocyanato groups of said organic polyisocyanate are bonded to an aromatic nucleus.
Claim 12
Dependent Claim
14 words
The method of claim 12 in which said organic polyisocyanate is a tolylene diisocyanate.
Claim 13
Dependent Claim
14 words
The method of claim 12 in which said organic polyisocyanate is a polyphenylmethylene polyisocyanate.
Claim 14
Dependent Claim
20 words
The method of claim 10 in which said organic polyisocyanate is a mixture of isomeric tolylene diisocyanates and polyphenylmethylene polyisocyanates.
Claim 15
Dependent Claim
30 words
The method of claim 10 in which said reaction mixture additionally contains a tertiary amine catalyst consisting of carbon, hydrogen and nitrogen and having no more than 12 carbon atoms.
Claim 16
Dependent Claim
14 words
The method of claim 16 in which said additional tertiary amine catalyst is triethylene-diamine.
Claim 17
Dependent Claim
14 words
The method of claim 16 in which said additional tertiary amine catalyst is N,N,N'',N''-tetramethyl-1,3-butanediamine.
Claim 18
Dependent Claim
46 words
The method of claim 10 in which said reaction mixture additionally contains a tertiary amine catalyst consisting of carbon, hydrogen, nitrogen and oxygen wherein said oxygen is present as an ether oxygen or a hydroxyl group, said additional catalyst having no more than 12 carbon atoms.
Claim 19
Dependent Claim
15 words
The method of claim 19 in which said additional tertiary amine catalyst is a bis(2-(N,N-dimethylamino)alkyl)ether.
Claim 20
Dependent Claim
15 words
The method of claim 19 in which said additional tertiary amine catalyst is an N-alkylmorpholine.
Claim 21
Dependent Claim
28 words
The method of claim 10 in which said amine catalyst componet (d) additionally includes a tertiary amine selected from the group consisting of triethylene-diamine, bis(2-(N,N-dimethylamino)ethyl)ether and mixtures thereof.
Claim 22
Dependent Claim
35 words
The method of claim 10 in which said reaction mixture additionally contains an organic derivative of tin selected from at least one of the group consisting of stannous salts of carboxylic acids and dialkyltin dicarboxylates.
Claim 23
Dependent Claim
23 words
The method of claim 10 in which said 3-dialkylamino-N,N-dimethylamide is added to the reaction mixture as a solution in a butanol-started polyoxyethylene-polyoxypropylene fluid.
Claim 24
Dependent Claim
23 words
The method of claim 10 in which said 3-dialkylamino-N,N-dimethylamide is added to the reaction mixture in combination with an organic non ionic surfactant.
Claim 25
Dependent Claim
18 words
The method of claim 25 in which said non ionic surfactant is an ethylene oxide adduct of nonylphenol.
Claim 26
Dependent Claim
14 words
The method of claim 10 in which said reaction mixture additionally contains a flame-retardant.
Claim 27
Dependent Claim
13 words
A flexible polyurethane foam produced in accordance with the method of claim 10.
Claim 28
Independent Claim
106 words
A method for producing a high resilience polyurethane foam which comprises reacting and foaming a reaction mixture containing: (a) an organic polyisocyanate reactant wherein the isocyanato groups are bonded to aromatic nuclei; (b) a polyether polyol having an average functionality of about 3, a hydroxyl number from about 21 to about 84 and a primary hydroxyl content from about 60 to about 90 mole per cent; (c) a polymer/polyol produced by the in situ polymerization of at least one polymerizable ethylenically unsaturated monomer in a polyether polyol; (d) water as a source of blowing action; and (e) a catalytic amount of a 3-dialkylamino-N,N-dimethylamide having the formula,
Claim 29
Dependent Claim
45 words
The method of claim 29 in which said polymer/polyol is a reaction product produced by polymerizing at least one monomer of the class consisting of styrene, alpha-methylstyrene, acrylonitrile and methacrylonitrile, in a polyether polyol having an average hydroxyl functionality from about 2.1 to about 4.
Claim 30
Dependent Claim
36 words
The method of claim 29 in which said polyether polyol component (b) and the polyol in which said polymer/polyol component (c) is polymerized, are glycerol-started polyoxypropylene ethers wherein the polyoxypropylene chains are capped with ethylene oxide.
Claim 31
Dependent Claim
20 words
The method of claim 29 in which a dialkyltin dicarboxylate is present as an additonal component of the reaction mixture.
Claim 32
Dependent Claim
11 words
The method of claim 29 in which said 3-dialkylamino-N,N-dimethylamide is 3-dimethylamino-N,N-dimethylpropionamide.
Claim 33
Dependent Claim
19 words
The method of claim 29 in which said reaction mixture contains bis(2-(N,N-dimethylamino)-ethyl) ether as an additonal catalytic Component thereof.
Claim 34
Dependent Claim
14 words
A high-resilience polyurethane foam produced as a product of the process of claim 19.
Claim 35
Dependent Claim
13 words
The method of claim 1 in which said alkyl beta-(dialkylamino)carboxylate is ethyl 3-(N,N-diethylamino)propionate.
Claim 36
Dependent Claim
14 words
The method of claim 9 in which said beta-amino carbonyl compound is N,N''-piperazino-bis(3-(N'''',N''''-dimethylpropionamide)) .
Claim 37
Dependent Claim
11 words
The method of claim 7 in which said 3-dialkylamino-N,N-dimethylamide is 3-diethylamino-N,N-dimethylpropionamide.
Claim 38
Dependent Claim
11 words
The method of claim 8 in which said 3-dialkylamino-N,N-dimethylamide is 3-dimethylamino-N,N-dimethylbutyramide.
Claim 39
Independent Claim
185 words
A method for producing a high resilience polyurethane foam which comprises reacting and foaming a reaction mixture containing: (a) an organic polyisocyanate comprising a tolylene diisocyanate; (b) a polyether triol having an average primary hydroxyl content of at least 40 mole per cent and an average molecular weight from about 2,000 to about 8,000; (c) a polymer/polyol prepared by the in situ polymerization of a monomer mixture containing from about 50 to about 75 weight per cent of acrylonitrile and from about 50 to about 25 weight per cent of styrene in a polyether triol having an average primary hydroxyl content of at least 40 mole per cent and an average molecular weight from about 2,000 to about 8,000; (d) water as a source of blowing action; (e) 3-dimethylamino-N,N-dimethylpropionamide and (f) at least one additional tertiary amine selected from the group consisting of triethylenediamine and bis(2-(N,N-dimethylamino)ethyl)ether, said components (e) and (f) being present in said reaction mixture in respective amounts between about 0.01 and about 5 parts by weight per 100 parts by weight of total polyols (b) and (c) contained in the reaction mixture.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1977-06-27 | 1977-12-27 | 1978-06-28 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1981-06-27 | 1981-12-27 | 1982-06-28 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1985-06-27 | 1985-12-27 | 1986-06-28 | $7700.00 | Window Closed / Lapsed |