← Back to Patent Explorer
US4033911A Expired / Lapsed US ⏱️ 0.0 years remaining

Process for catalyzing polyurethane foam formation using N,N-dimethyl-aminoalkoxy-propionitriles

Assignee: OSI Specialties Inc
•
Filing: 1976-06-24
•
Granted: 1977-07-05
•
Expires: 1996-06-24
📄 Original PDF 🌐 Google Patents 🔄 Sync Now

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 an N,N-dimethylaminoalkoxypropionitrile. The said N,N-dimethylaminoalkoxypropionitriles 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 products. Especially preferred for use in the practice of the invention are 3-(2-dimethylaminoethoxy)propionitrile and 3-[2-(2-dimethylaminoethoxy)ethoxy]propionitrile 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 dimethylaminoalkoxypropionitriles.

Inventors

  • 👤 Michael Ray Sandner
  • 👤 Bela Prokai

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-06 08:41
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/08; C08G18/16; C08G18/18; C08G18/185; Y; Y10; Y10S; Y10S521/00; Y10S521/904

Claims Analysis

Total Claims: 44
Claim 1
Independent Claim 137 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 isocyanate functionality of at least two; (3) a blowing agent; and (4) a catalytically effective amount of a catalyst system comprising an N,N-dimethylaminoalkoxypropionitrile having the formula, ##STR11## 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 137 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 isocyanate functionality of at least two; (3) a blowing agent; and (4) a catalytically effective amount of a catalyst system comprising an N,N-dimethylaminoalkoxypropionitrile having the formula, ##STR11## 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 22 words
A method as defined in claim 1 in which the value of n of said N,N-dimethylaminoalkoxypropionitrile 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 32 words
A method as defined in claim 1 in which each of R 1 through R 4 of said N,N-dimethylaminoalkoxypropionitrile is hydrogen and the value of n is no more than about three.
Claim 6
Dependent Claim 13 words
A method as defined in claim 1 in which said N,N-dimethylaminoalkoxypropionitrile is 3-(2-dimethylaminoethoxy)propionitrile.
Claim 7
Dependent Claim 13 words
A method as defined in claim 1 in which said N,N-dimethylaminoethoxypropionitrile is 3-[2-(2-dimethylaminoethoxy)ethoxy]propionitrile.
Claim 8
Dependent Claim 24 words
A method as defined in claim 1 in which said catalyst system additionally contains at least one other tertiary-amine component different from said N,N-dimethylaminoalkoxypropionitriles.
Claim 9
Dependent Claim 21 words
A method as defined in claim 7 in which said other tertiary-amine component of the catalyst system is a hydrocarbyl polyamine.
Claim 10
Dependent Claim 16 words
A method as defined in claim 7 in which said other tertiary-amine component is a 3-dimethylamino-N,N-dimethylpropionamide.
Claim 11
Dependent Claim 15 words
A method as defined in claim 7 in which said other tertiary-amine component is N,N-dimethylethanolamine.
Claim 12
Dependent Claim 15 words
A method as defined in claim 7 in which said other tertiary-amine component is N,N-dimethylcyclohexylamine.
Claim 13
Dependent Claim 19 words
A method as defined in claim 1 in which said catalyst system additionally contains an organic compound of tin.
Claim 14
Dependent Claim 22 words
A method as defined in claim 12 in which said organic compound of tin is a stannous salt of a carboxylic acid.
Claim 15
Dependent Claim 18 words
A method as defined in claim 12 in which said organic compound of tin is a dialkyltin dicarboxylate.
Claim 16
Dependent Claim 33 words
A method as defined in claim 1 in which said catalyst system contains at least one other tertiary-amine component which is different from said N,N-dimethylaminoalkoxypropionitrile and at least one organic compound of tin.
Claim 17
Independent Claim 85 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) a catalytically effective amount of a catalyst system containing an N,N-dimethylaminoalkoxypropionitrile component having the formula, (CH 3 ) 2 N--(CH 2 --CH 2 --O) n --CH 2 CH 2 C.tbd.N, where n has a value from one to about five.
Claim 18
Independent Claim 85 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) a catalytically effective amount of a catalyst system containing an N,N-dimethylaminoalkoxypropionitrile component having the formula, (CH 3 ) 2 N--(CH 2 --CH 2 --O) n --CH 2 CH 2 C.tbd.N, where n has a value from one to about five.
Claim 19
Independent Claim 88 words
A method for producing flexible polyether urethane foam which comprises simultaneously reacting and foaming an organic polyisocyanate reactant and 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 0.05 to about 4 parts by weight per 100 parts by weight of total polyol reactant of a catalyst system comprising at least one N,N-dimethylaminoalkoxypropionitrile selected from the group consisting of 3-(2-dimethylaminoethoxy)propionitrile and 3-[2-(2-dimethylaminoethoxy)ethoxy]propionitrile.
Claim 20
Independent Claim 88 words
A method for producing flexible polyether urethane foam which comprises simultaneously reacting and foaming an organic polyisocyanate reactant and 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 0.05 to about 4 parts by weight per 100 parts by weight of total polyol reactant of a catalyst system comprising at least one N,N-dimethylaminoalkoxypropionitrile selected from the group consisting of 3-(2-dimethylaminoethoxy)propionitrile and 3-[2-(2-dimethylaminoethoxy)ethoxy]propionitrile.
Claim 21
Dependent Claim 37 words
A method as defined in claim 17 wherein said catalyst system additionally contains (1) at least one other tertiary-amine component which is different from said N,N-dimethylaminoalkoxypropionitrile and (2) at least one of stannous octoate and dibutyltin dilaurate.
Claim 22
Independent Claim 92 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 1,000 in the presence of a blowing agent comprising a fluorocarbon and 0.1 to about 10 parts by weight per 100 parts by weight of total polyol reactant of an amine catalyst system comprising at least one N,N-dimethylaminoalkoxypropionitrile selected from the group consisting of 3-(2-dimethylaminoethoxy)propionitrile and 3-[2-dimethylaminoethoxy)ethoxy]propionitrile.
Claim 23
Independent Claim 92 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 1,000 in the presence of a blowing agent comprising a fluorocarbon and 0.1 to about 10 parts by weight per 100 parts by weight of total polyol reactant of an amine catalyst system comprising at least one N,N-dimethylaminoalkoxypropionitrile selected from the group consisting of 3-(2-dimethylaminoethoxy)propionitrile and 3-[2-dimethylaminoethoxy)ethoxy]propionitrile.
Claim 24
Dependent Claim 19 words
A method as defined in claim 19 in which said catalyst system additionally contains an organic compound of tin.
Claim 25
Dependent Claim 17 words
A method as defined in claim 20 in which said organic compound of tin is dibutyltin dilaurate.
Claim 26
Dependent Claim 19 words
A method as defined in claim 19 in which said catalyst system additionally contains at least one hydrocarbyl polyamine.
Claim 27
Dependent Claim 28 words
A method as defined in claim 22 in which said hydrocarbyl polyamine is at least one member of the group consisting of triethylenediamine, N,N,N',N'-tetraethylethylenediamine N,N,N', N'-tetramethyl-1,3-butanediamine and 1,1,4,7,7-pentamethyldiethylenetriamine.
Claim 28
Dependent Claim 15 words
A method as defined in claim 19 in which said catalyst system additionally contains N,N-dimethylcyclohexylamine.
Claim 29
Dependent Claim 15 words
A method as defined in claim 19 in which said catalyst system additionally contains 3-dimethylamino-N,N-dimethylpropionamide.
Claim 30
Dependent Claim 16 words
A method as defined in claim 25 in which said catalyst system additionally contains dibutyltin dilaurate.
Claim 31
Dependent Claim 16 words
A method as defined in claim 19 in which the blowing agent is fluorocarbon or chlorocarbon.
Claim 32
Dependent Claim 15 words
A method as defined in claim 19 in which the blowing agent additionally contains water.
Claim 33
Dependent Claim 16 words
A method as defined in claim 19 in which said organic polyisocyanate comprises a polymeric isocyanate.
Claim 34
Dependent Claim 29 words
A method as defined in claim 19 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 35
Dependent Claim 17 words
A method as defined in claim 19 in which said polyether polyol is a nitrogen-containing polyether polyol.
Claim 36
Independent Claim 83 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) a catalytically effective amount of a catalyst system comprising at least one N,N-dimethylaminoalkoxypropionitrile having the formula: (CH.sub.3).sub.2 N--(CH.sub.2 --CH.sub.2 --O).sub.n --CH.sub.2 CH.sub.2 C.tbd.N wherein n n has the value from one to about five.
Claim 37
Independent Claim 83 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) a catalytically effective amount of a catalyst system comprising at least one N,N-dimethylaminoalkoxypropionitrile having the formula: (CH.sub.3).sub.2 N--(CH.sub.2 --CH.sub.2 --O).sub.n --CH.sub.2 CH.sub.2 C.tbd.N wherein n n has the value from one to about five.
Claim 38
Dependent Claim 12 words
A method as defined in claim 32 wherein said N,N-dimethylaminoalkoxypropionitrile is 3-(2-dimethylaminoethoxy)propionitrile.
Claim 39
Dependent Claim 13 words
A method as defined in claim 32 in which said N,N-dimethylaminoalkoxypropionitrile is 3-[2-(2-dimethylaminoethoxy)ethoxy]propionitrile.
Claim 40
Dependent Claim 57 words
A method as defined in claim 32 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 hyroxyl groups.
Claim 41
Independent Claim 174 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) 0.1 to about 10 parts by weight per 100 parts by weight of total polyol reactant of a catalyst system comprising at least one of 3-(2-dimethylaminoethoxy)propionitrile and 3-[2-(2-dimethylaminoethoxy)ethoxy]propionitrile as essentially the sole catalytic component of the reaction mixture or in combination with at least one of (i) and (ii) where (i) is another tertiary-amine component and (ii) is an organic compound of tin.
Claim 42
Independent Claim 174 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) 0.1 to about 10 parts by weight per 100 parts by weight of total polyol reactant of a catalyst system comprising at least one of 3-(2-dimethylaminoethoxy)propionitrile and 3-[2-(2-dimethylaminoethoxy)ethoxy]propionitrile as essentially the sole catalytic component of the reaction mixture or in combination with at least one of (i) and (ii) where (i) is another tertiary-amine component and (ii) is an organic compound of tin.
Claim 43
Independent Claim 172 words
A method for producing high-resilience 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 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) 0.05 to about 4 parts by weight per 100 parts by weight of total polyol reactant of a catalyst system comprising at least one of 3-(2-dimethylaminoethoxy)propionitrile and 3-[2-(2-dimethylaminoethoxy)ethoxy]propionitrile as essentially the sole catalytic components of the reaction mixture or in combination with at least one of (i) and (ii) where (i) is another tertiary-amine component and (ii) is an organic compound of tin.
Claim 44
Independent Claim 172 words
A method for producing high-resilience 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 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) 0.05 to about 4 parts by weight per 100 parts by weight of total polyol reactant of a catalyst system comprising at least one of 3-(2-dimethylaminoethoxy)propionitrile and 3-[2-(2-dimethylaminoethoxy)ethoxy]propionitrile as essentially the sole catalytic components of the reaction mixture or in combination with at least one of (i) and (ii) where (i) is another tertiary-amine component and (ii) is an organic compound of tin.

References Cited (Backward Citations)

CA676183A Cited
US2941967A Cited
GB879167A Cited
GB893240A Cited
US3330782A Cited
US3478096A Cited
US3660319A Cited
US3925268A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1980-07-04 1981-01-03 1981-07-05 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1984-07-04 1985-01-03 1985-07-05 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1988-07-04 1989-01-03 1989-07-05 $7700.00 Window Closed / Lapsed

Assigned Categories & Tags

No categories assigned to this patent yet.

Assign Category Tag