US4049931A
Expired / Lapsed
US
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Catalyst systems containing dimethylamino ether mono-ols for polyurethane foam formation
Assignee: OSI Specialties Inc
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Filing: 1975-05-29
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Granted: 1977-09-20
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Expires: 1995-05-29
Abstract
Abstract Cellular urethane polymers are provided by effecting the reaction of an organic polyol reactant comprising a polyether polyol and an organic polyisocyanate reactant in the presence of a blowing agent and a catalyst system comprising a tertiary-dimethylamino ether mono-ol. In the dimethylamino ether mono-ols employed as catalysts in the practice of the invention, the tertiary-dimethylamino group and the hydroxyl group are positioned beta to a common acyclic ether oxygen atom or to different acyclic ether oxygen atoms which in turn are positioned beta to one another. The said dimethylamino ether mono-ols are versatile, low odor catalysts and are useful in forming cellular urethane polymers ranging from all water-blown flexible polyether foam to all fluorocarbon-blown rigid foam including semi-flexible and high-resilience foam products. Especially preferred for use in the practice of the invention are 2-(2-dimethylaminoethoxy)ethanol and 2-[2-(2-dimethylaminoethoxy)ethoxy]ethanol either as such or in combination with other catalysts including other tertiary-amine components and/or organic compounds of tin. Also provided are blended catalyst systems comprising said dimethylamino ether mono-ols.
Inventors
- 👤 Michael Ray Sandner
- 👤 Robert Donovan Duffy
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 05:27
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/08; C08G18/16; C08G18/18; C08G18/1825; C08G18/28; C08G18/2805; C08G18/285; C08G18/2875; C08G2110/00; C08G2110/0008; C08G2110/0016; C08G2110/0025; C08G2110/0083
Claims Analysis
Total Claims: 57
Claim 1
Independent Claim
204 words
A method for producing a cellular urethane polymer which comprises reacting and foaming a reaction mixture containing: (1) an organic polyol reactant comprising a polyether polyol having an average hydroxyl functionality of at least two; (2) an organic polyisocyanate reactant having an average isocyanato functionality of at least two; (3) a blowing agent; and (4) a catalytically effective amount of a catalyst system comprising from about 10 to about 95 weight percent of component (i) and from about 90 to about 5 weight percent of component (ii), said percentages being based on the combined total weight of components (i) and (ii) contained in the reaction mixture, where component (i) is at least one dimethylamino ether mono-ol and component (ii) is at least one other tertiary-amine different from component (i), said dimethylamino ether mono-ol having the formula, ##STR23## wherein: R 1 and R 2 each represents hydrogen, methyl or ethyl provided R 1 and R 2 cumulatively have no more than two carbon atoms; R 3 and R 4 each represents hydrogen, methyl or ethyl provided R 3 and R 4 cumulatively have no more than two carbon atoms; and n has an average value of at least one and no more than about five.
Claim 2
Independent Claim
204 words
A method for producing a cellular urethane polymer which comprises reacting and foaming a reaction mixture containing: (1) an organic polyol reactant comprising a polyether polyol having an average hydroxyl functionality of at least two; (2) an organic polyisocyanate reactant having an average isocyanato functionality of at least two; (3) a blowing agent; and (4) a catalytically effective amount of a catalyst system comprising from about 10 to about 95 weight percent of component (i) and from about 90 to about 5 weight percent of component (ii), said percentages being based on the combined total weight of components (i) and (ii) contained in the reaction mixture, where component (i) is at least one dimethylamino ether mono-ol and component (ii) is at least one other tertiary-amine different from component (i), said dimethylamino ether mono-ol having the formula, ##STR23## wherein: R 1 and R 2 each represents hydrogen, methyl or ethyl provided R 1 and R 2 cumulatively have no more than two carbon atoms; R 3 and R 4 each represents hydrogen, methyl or ethyl provided R 3 and R 4 cumulatively have no more than two carbon atoms; and n has an average value of at least one and no more than about five.
Claim 3
Dependent Claim
24 words
A method as defined in claim 1 in which the value of n of said dimethylamino ether mono-ol is no more than about three.
Claim 4
Dependent Claim
38 words
A method as defined in claim 1 in which R 1 and R 2 taken together have no more than one carbon atom, and R 3 and R 4 taken together have no more than one carbon atom.
Claim 5
Dependent Claim
34 words
A method as defined in claim 1 in which each of R 1 through R 4 of said dimethylamino ether mono-ol is hydrogen and the value of n is no more than about three.
Claim 6
Dependent Claim
15 words
A method as defined in claim 1 in which said dimethylamino ether mono-ol is 2-(2-dimethylaminoethoxy)-ethanol.
Claim 7
Dependent Claim
15 words
A method as defined in claim 1 in which said dimethylamino ether mono-ol is 2-[2-(2-dimethylaminoethoxy)ethoxy]ethanol.
Claim 8
Dependent Claim
38 words
A method as defined in claim 1 in which the dimethylamino ether mono-ol component of the catalyst system is a distillable by-product which contains 2-[2-(2-dimethylaminoethoxy)ethoxy]ethanol and is formed in the preparation of 2-(2-dimethylaminoethoxy)ethanol by the oxyethylation of N,N-dimethylethanolamine.
Claim 9
Dependent Claim
20 words
A method as defined in claim 1 in which said other tertiary-amine component of the catalyst system is a bis[2-(N,N-dimethylamino)alkyl]ether.
Claim 10
Dependent Claim
13 words
A method as defined in claim 8 in which said bis-ether is bis[2-(N,N-dimethylamino)ethyl]ether.
Claim 11
Dependent Claim
61 words
A method as defined in claim 1 in which said other tertiary-amine component is a distillable by-product formed in the preparation of bis[2-(N,N-dimethylamino)ethyl]ether by the reaction of trimethylamine and 2-(2-dimethylaminoethoxy)ethanol in the presence of a nickel catalyst at a temperature from about 50° C. to about 300° C. employing from one to about 10 moles of trimethylamine per mole of 2-(2-dimethylaminoethoxy)-ethanol.
Claim 12
Dependent Claim
21 words
A method as defined in claim 1 in which said other tertiary-amine component of the catalyst system is a hydrocarbyl polyamine.
Claim 13
Dependent Claim
15 words
A method as defined in claim 1 in which said other tertiary-amine component is 3-dimethylamino-N,N-dimethylpropionamide.
Claim 14
Dependent Claim
15 words
A method as defined in claim 1 in which said other tertiary-amine component is N,N-dimethylethanolamine.
Claim 15
Dependent Claim
15 words
A method as defined in claim 1 in which said other tertiary-amine component is N,N-dimethylcyclohexylamine.
Claim 16
Dependent Claim
19 words
A method as defined in claim 1 in which said catalyst system additionally contains an organic compound of tin.
Claim 17
Dependent Claim
22 words
A method as defined in claim 15 in which said organic compound of tin is a stannous salt of a carboxylic acid.
Claim 18
Dependent Claim
18 words
A method as defined in claim 15 in which said organic compound of tin is a dialkyltin dicarboxylate.
Claim 19
Independent Claim
164 words
A method for producing cellular polyurethanes which comprises reacting and foaming a reaction mixture containing: (1) an organic polyol reactant comprising a polyether polyol having an average hydroxyl functionality from about two to about eight; (2) an organic polyisocyanate; (3) a blowing agent; and (4) from about 0.05 to about 10 parts by weight per one hundred parts by weight of total organic polyol reactant contained in the reaction mixture, of a catalyst system containing from about 10 to about 90 weight percent of component (i) which is a dimethylamino ether mono-ol having the formula, (CH 3 ) 2 N--CH 2 CH 2 --O--(CH 2 CH 2 O) n --H, where n has an average value from one to about five, and from about 90 to about 10 weight percent of component (ii) which is at least one other tertiary-amine different from component (i), said weight percentages being based on the combined total weight of components (i) and (ii) contained in the reaction mixture.
Claim 20
Independent Claim
164 words
A method for producing cellular polyurethanes which comprises reacting and foaming a reaction mixture containing: (1) an organic polyol reactant comprising a polyether polyol having an average hydroxyl functionality from about two to about eight; (2) an organic polyisocyanate; (3) a blowing agent; and (4) from about 0.05 to about 10 parts by weight per one hundred parts by weight of total organic polyol reactant contained in the reaction mixture, of a catalyst system containing from about 10 to about 90 weight percent of component (i) which is a dimethylamino ether mono-ol having the formula, (CH 3 ) 2 N--CH 2 CH 2 --O--(CH 2 CH 2 O) n --H, where n has an average value from one to about five, and from about 90 to about 10 weight percent of component (ii) which is at least one other tertiary-amine different from component (i), said weight percentages being based on the combined total weight of components (i) and (ii) contained in the reaction mixture.
Claim 21
Dependent Claim
63 words
A method as defined in claim 18 wherein said component (ii) of the catalyst system contains a distillable by-product formed in the preparation of bis[2-(N,N-dimethylamino)ethyl]ether by the reaction of trimethylamine and 2-(2-dimethylaminoethoxy)ethanol in the presence of a nickel catalyst at a temperature from about 140° C. to about 200° C. employing from two to about five moles of trimethylamine per mole of 2-(2-dimethylaminoethoxy)ethanol.
Claim 22
Dependent Claim
38 words
A method as defined in claim 19 in which the dimethylamino ether mono-ol component of the catalyst system is a distillable by-product which contains 2-[2-(2-dimethylaminoethoxy)ethoxy]ethanol and is formed in the preparation of 2-(2-dimethylaminoethoxy)ethanol by the oxyethylation of N,N-dimethylethanolamine.
Claim 23
Dependent Claim
20 words
A method as defined in claim 19 in which said dimethylamino ether mono-ol component of the catalyst system is 2-(2-dimethylaminoethoxy)ethanol.
Claim 24
Dependent Claim
17 words
A method as defined in claim 21 in which component (ii) of said catalyst system contains bis[2-(N,N-dimethylamino)ethyl]ether.
Claim 25
Dependent Claim
17 words
A method as defined in claim 21 in which component (ii) of said catalyst system contains N,N-dimethylethanolamine.
Claim 26
Independent Claim
168 words
A method for producing a cellular urethane polymer which comprises reacting and foaming a reaction mixture containing (1) an organic polyisocyanate, (2) a polymer/polyether polyol produced by the in situ polymerization of at least one polymerizable ethylenically unsaturated monomer in a polyether polyol, (3) a blowing agent, and (4) from about 0.05 to about 10 parts by weight per one hundred parts by weight of total polyol contained in the reaction mixture, of a catalyst system comprising from about 10 to about 90 weight percent of component (i) which is at least one dimethylamino ether mono-ol having the formula, (CH 3 ) 2 N--CH 2 CH 2 --O--(CH 2 CH 2 O) n --H, where n has an average value from one to about three, and from about 90 to about 10 weight percent of component (ii) which is at least one other tertiary-amine different from component (i), said weight percentages being based on the combined total weight of components (i) and (ii) contained in the reaction mixture.
Claim 27
Independent Claim
168 words
A method for producing a cellular urethane polymer which comprises reacting and foaming a reaction mixture containing (1) an organic polyisocyanate, (2) a polymer/polyether polyol produced by the in situ polymerization of at least one polymerizable ethylenically unsaturated monomer in a polyether polyol, (3) a blowing agent, and (4) from about 0.05 to about 10 parts by weight per one hundred parts by weight of total polyol contained in the reaction mixture, of a catalyst system comprising from about 10 to about 90 weight percent of component (i) which is at least one dimethylamino ether mono-ol having the formula, (CH 3 ) 2 N--CH 2 CH 2 --O--(CH 2 CH 2 O) n --H, where n has an average value from one to about three, and from about 90 to about 10 weight percent of component (ii) which is at least one other tertiary-amine different from component (i), said weight percentages being based on the combined total weight of components (i) and (ii) contained in the reaction mixture.
Claim 28
Dependent Claim
14 words
A method as defined in claim 24 wherein said dimethylamino ether mono-ol is 2-(2-dimethylaminoethoxy)ethanol.
Claim 29
Dependent Claim
15 words
A method as defined in claim 24 in which said dimethylamino ether mono-ol is 2-[2-(2-dimethylaminoethoxy)ethoxy]ethanol.
Claim 30
Dependent Claim
57 words
A method as defined in claim 24 in which said reaction mixture additionally contains a polyether polyol reactant having an average functionality from 2.1 to about 5, a hydroxyl number from about 18 to about 40, and an average hydroxyl content which is constituted of between about 35 and about 85 mole percent of primary hydroxyl groups.
Claim 31
Independent Claim
130 words
A method for producing flexible polyether urethane foam which comprises simultaneously reacting and foaming a polyether polyol having an average hydroxyl functionality from 2 to about 4 and a hydroxyl number from about 20 to about 125 in the presence of water as a source of blowing action, and from about 0.05 to about 4 parts by weight per one hundred parts by weight of polyether polyol contained in the reaction mixture, of a catalyst system comprising from about 10 to about 90 weight percent of component (i) and from about 90 to about 10 weight percent of component (ii), said weight percentages being based on the combined total weight of components (i) and (ii) contained in the reaction mixture, where component (i) is 2-(2-dimethylaminoethoxy)ethanol and component (ii) is bis[2-(N,N-dimethylamino)ethyl]ether.
Claim 32
Independent Claim
130 words
A method for producing flexible polyether urethane foam which comprises simultaneously reacting and foaming a polyether polyol having an average hydroxyl functionality from 2 to about 4 and a hydroxyl number from about 20 to about 125 in the presence of water as a source of blowing action, and from about 0.05 to about 4 parts by weight per one hundred parts by weight of polyether polyol contained in the reaction mixture, of a catalyst system comprising from about 10 to about 90 weight percent of component (i) and from about 90 to about 10 weight percent of component (ii), said weight percentages being based on the combined total weight of components (i) and (ii) contained in the reaction mixture, where component (i) is 2-(2-dimethylaminoethoxy)ethanol and component (ii) is bis[2-(N,N-dimethylamino)ethyl]ether.
Claim 33
Dependent Claim
22 words
A method as defined in claim 28 wherein said catalyst system additionally contains at least one of stannous octoate and dibutyltin dilaurate.
Claim 34
Independent Claim
159 words
A method for producing rigid urethane foam which comprises reacting and foaming an organic polyisocyanate reactant and an organic polyol reactant comprising a polyether polyol having an average hydroxyl functionality from about 3 to about 8 and a hydroxyl number from about 200 to about 1000 in the presence of a blowing agent comprising fluorocarbon and from about 0.1 to about 10 parts by weight per one hundred parts by weight of total polyol contained in the reaction mixture, of a catalyst system comprising from about 10 to about 90 weight percent of component (i) and from about 90 to about 10 weight percent of component (ii), said weight percentages being based on the combined total weight of components (i) and (ii) contained in the reaction mixture, wherein component (i) is at least one tertiary-dimethylamino ether mono-ol selected from the group consisting of 2-(2-dimethylaminoethoxy)ethanol and 2-[2-(2-dimethylaminoethoxy)ethoxy]ethanol, and component (ii) is at least one other tertiary-amine different from component (i).
Claim 35
Independent Claim
159 words
A method for producing rigid urethane foam which comprises reacting and foaming an organic polyisocyanate reactant and an organic polyol reactant comprising a polyether polyol having an average hydroxyl functionality from about 3 to about 8 and a hydroxyl number from about 200 to about 1000 in the presence of a blowing agent comprising fluorocarbon and from about 0.1 to about 10 parts by weight per one hundred parts by weight of total polyol contained in the reaction mixture, of a catalyst system comprising from about 10 to about 90 weight percent of component (i) and from about 90 to about 10 weight percent of component (ii), said weight percentages being based on the combined total weight of components (i) and (ii) contained in the reaction mixture, wherein component (i) is at least one tertiary-dimethylamino ether mono-ol selected from the group consisting of 2-(2-dimethylaminoethoxy)ethanol and 2-[2-(2-dimethylaminoethoxy)ethoxy]ethanol, and component (ii) is at least one other tertiary-amine different from component (i).
Claim 36
Dependent Claim
19 words
A method as defined in claim 30 in which said catalyst system additionally contains an organic compound of tin.
Claim 37
Dependent Claim
22 words
A method as defined in claim 31 in which said organic compound of tin is a stannous salt of a carboxylic acid.
Claim 38
Dependent Claim
18 words
A method as defined in claim 31 in which said organic compound of tin is a dialkyltin dicarboxylate.
Claim 39
Dependent Claim
15 words
A method as defined in claim 33 in which said dialkyltin dicarboxylate is dibutyltin dilaurate.
Claim 40
Dependent Claim
22 words
A method as defined in claim 31 in which said organic compound of tin is a dialkyltin oxide or a trialkyltin oxide.
Claim 41
Dependent Claim
18 words
A method as defined in claim 31 in which said organic compound of tin is a tin mercaptide.
Claim 42
Dependent Claim
20 words
A method as defined in claim 30 in which said other tertiary-amine encompassed by component (ii) is a hydrocarbyl polyamine.
Claim 43
Dependent Claim
28 words
A method as defined in claim 37 in which said hydrocarbyl polyamine is at least one member of the group consisting of triethylenediamine, N,N,N',N'-tetramethylethylenediamine, N,N,N',N'-tetraethylethylenediamine, N,N,N',N'-tetramethyl-1,3-butanediamine and 1,1,4,7,7-pentamethyldiethylenetriamine.
Claim 44
Dependent Claim
18 words
A method as defined in claim 30 in which said other tertiary-amine encompassed by component (ii) is N,N-dimethylcyclohexylamine.
Claim 45
Dependent Claim
18 words
A method as defined in claim 30 in which said other tertiary-amine encompassed by component (ii) is 3-dimethylamino-N,N-dimethylpropionamide.
Claim 46
Dependent Claim
19 words
A method as defined in claim 40 in which said catalyst system additionally contains an organic compound of tin.
Claim 47
Dependent Claim
14 words
A method as defined in claim 30 in which the blowing agent is fluorocarbon.
Claim 48
Dependent Claim
15 words
A method as defined in claim 30 in which the blowing agent additionally contains water.
Claim 49
Dependent Claim
16 words
A method as defined in claim 30 in which said organic polyisocyanate comprises a polymeric isocyanate.
Claim 50
Dependent Claim
28 words
A method as defined in claim 30 in which said organic polyisocyanate comprises tolylene diisocyanate residue obtained from the manufacture of the 2,4- and 2,6-isomers of tolylene diisocyanate.
Claim 51
Dependent Claim
17 words
A method as defined in claim 30 in which said polyether polyol is a nitrogen-containing polyether polyol.
Claim 52
Independent Claim
207 words
A method for producing semi-flexible polyurethane foam which comprises reacting and foaming a reaction mixture containing (1) an organic polyisocyanate; (2) an organic polyol reactant which is constituted of (a) from about 50 to 100 percent by weight of a polymer/polyether polyol produced by the in situ polymerization of an ethylenically unsaturated monomer in a polyether polyol and (b) from zero up to about 50 percent by weight of a polyether polyol having an average hydroxyl functionality from 2.1 to about 5, a hydroxyl number from about 18 to about 40 and an average primary hydroxyl content between about 35 and about 85 mole percent; (3) a blowing agent; and (4) from about 0.1 to about 10 parts by weight per one hundred parts by weight of total polyol reactant contained in the reaction mixture, of a catalyst system comprising from about 10 to about 90 weight percent of component (i) and from about 90 to about 10 weight percent of component (ii), said weight percentages being based on the combined total weight of components (i) and (ii) contained in the reaction mixture, where component (i) is at least one of 2-(2-dimethylaminoethoxy)ethanol and 2-[2-(2-dimethylaminoethoxy)ethoxy]ethanol, and component (ii) is at least one other tertiary-amine different from component (i).
Claim 53
Independent Claim
207 words
A method for producing semi-flexible polyurethane foam which comprises reacting and foaming a reaction mixture containing (1) an organic polyisocyanate; (2) an organic polyol reactant which is constituted of (a) from about 50 to 100 percent by weight of a polymer/polyether polyol produced by the in situ polymerization of an ethylenically unsaturated monomer in a polyether polyol and (b) from zero up to about 50 percent by weight of a polyether polyol having an average hydroxyl functionality from 2.1 to about 5, a hydroxyl number from about 18 to about 40 and an average primary hydroxyl content between about 35 and about 85 mole percent; (3) a blowing agent; and (4) from about 0.1 to about 10 parts by weight per one hundred parts by weight of total polyol reactant contained in the reaction mixture, of a catalyst system comprising from about 10 to about 90 weight percent of component (i) and from about 90 to about 10 weight percent of component (ii), said weight percentages being based on the combined total weight of components (i) and (ii) contained in the reaction mixture, where component (i) is at least one of 2-(2-dimethylaminoethoxy)ethanol and 2-[2-(2-dimethylaminoethoxy)ethoxy]ethanol, and component (ii) is at least one other tertiary-amine different from component (i).
Claim 54
Dependent Claim
19 words
A method as defined in claim 47 in which said catalyst system additionally contains an organic compound of tin.
Claim 55
Independent Claim
205 words
A method for producing high-resilience polyurethane foam which comprises reacting and foaming a reaction mixture containing (1) an organic polyisocyante; (2) an organic polyol reactant which is constituted of (a) from about 20 to about 60 weight percent of a polymer/polyether polyol produced by the in situ polymerization of an ethylenically unsaturated monomer in a polyether polyol and (b) from about 80 to about 40 weight percent of a polyether polyol having an average hydroxyl functionality from 2.1 to about 5, a hydroxyl number from 18 to about 40 and an average primary hydroxyl content between about 35 and about 85 mole percent; (3) a blowing agent; and (4) from about 0.05 to about 4 parts by weight per one hundred parts by weight of total organic polyol contained in the reaction mixture, of a catalyst system comprising from about 10 to about 90 weight percent of component (i) and from about 90 to about 10 weight percent of component (ii), said weight percentages being based on the combined total weight of components (i) and (ii) contained in the reaction mixture, where component (i) is at least one of 2-(2-dimethylaminoethoxy)ethanol and 2-[2-(2-dimethylaminoethoxy)ethoxy]ethanol, and component (ii) is at least one other tertiaryamine different from component (i).
Claim 56
Independent Claim
205 words
A method for producing high-resilience polyurethane foam which comprises reacting and foaming a reaction mixture containing (1) an organic polyisocyante; (2) an organic polyol reactant which is constituted of (a) from about 20 to about 60 weight percent of a polymer/polyether polyol produced by the in situ polymerization of an ethylenically unsaturated monomer in a polyether polyol and (b) from about 80 to about 40 weight percent of a polyether polyol having an average hydroxyl functionality from 2.1 to about 5, a hydroxyl number from 18 to about 40 and an average primary hydroxyl content between about 35 and about 85 mole percent; (3) a blowing agent; and (4) from about 0.05 to about 4 parts by weight per one hundred parts by weight of total organic polyol contained in the reaction mixture, of a catalyst system comprising from about 10 to about 90 weight percent of component (i) and from about 90 to about 10 weight percent of component (ii), said weight percentages being based on the combined total weight of components (i) and (ii) contained in the reaction mixture, where component (i) is at least one of 2-(2-dimethylaminoethoxy)ethanol and 2-[2-(2-dimethylaminoethoxy)ethoxy]ethanol, and component (ii) is at least one other tertiaryamine different from component (i).
Claim 57
Dependent Claim
19 words
A method as defined in claim 49 in which said catalyst system additionally contains an organic compound of tin.
References Cited (Backward Citations)
US2941967A
Cited
US3341482A
Cited
US3520835A
Cited
US3478096A
Cited
GB1166742A
Cited
US3573255A
Cited
US3853818A
Cited
US3931387A
Cited
US3890255A
Cited
US3899443A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-09-19 | 1981-03-21 | 1981-09-20 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-09-19 | 1985-03-21 | 1985-09-20 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-09-19 | 1989-03-21 | 1989-09-20 | $7700.00 | Window Closed / Lapsed |