US4521546A
Expired / Lapsed
US
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Graft copolymers from vinyl monomers and polyurethane oligomers and polyurethanes prepared therefrom
Assignee: Arch Chemicals Inc
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Filing: 1983-07-06
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Granted: 1985-06-04
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Expires: 2003-07-06
Abstract
Abstract Graft copolymers are prepared by the copolymerization of an ethylenically unsaturated monomer, or a mixture of such monomers, with a polyurethane oligomer in a polyol. The polyurethane oligomer is the reaction product of an isocyanate-terminated prepolymer with an isocyanate reactive group-containing unsaturated monomer. The graft copolymers are useful in polyurethane formulations.
Inventors
- 👤 James M. O'Connor
- 👤 Donald L. Lickei
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 11:42
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/28; C08G18/67; C08G18/671; C08F; C08F299/00; C08F299/02; C08F299/06; C08G18/40; C08G18/63; C08G18/635; C08L; C08L75/00; C08L75/04
Claims Analysis
Total Claims: 28
Claim 1
Independent Claim
155 words
A process for preparing a graft copolymer comprising: (a) reacting at least one organic polyisocyanate with at least one polyol having an average equivalent weight from about 100 to about 6000 in an equivalent ratio of NCO to OH from about 1.02/1 to about 2/1 to yield an isocyanate-terminated prepolymer; (b) reacting said isocyanate-terminated prepolymer with at least one isocyanate reactive group-containing unsaturated monomer in sufficient proportions to form a polyurethane oligomer having a final free NCO content from about 0% to about 1% by weight and having terminal reactive unsaturation; and (c) copolymerizing said polyurethane oligomer with at least one ethylenically unsaturated monomer in the presence of at least one polyol and in the presence of a catalytically effective amount of a free radical catalyst at a temperature from about 80° C. to about 170° C. to form a dispersion of a graft copolymer of said oligomer and said monomer in a polyol medium.
Claim 2
Dependent Claim
155 words
A process for preparing a graft copolymer comprising: (a) reacting at least one organic polyisocyanate with at least one polyol having an average equivalent weight from about 100 to about 6000 in an equivalent ratio of NCO to OH from about 1.02/1 to about 2/1 to yield an isocyanate-terminated prepolymer; (b) reacting said isocyanate-terminated prepolymer with at least one isocyanate reactive group-containing unsaturated monomer in sufficient proportions to form a polyurethane oligomer having a final free NCO content from about 0% to about 1% by weight and having terminal reactive unsaturation; and (c) copolymerizing said polyurethane oligomer with at least one ethylenically unsaturated monomer in the presence of at least one polyol and in the presence of a catalytically effective amount of a free radical catalyst at a temperature from about 80° C. to about 170° C. to form a dispersion of a graft copolymer of said oligomer and said monomer in a polyol medium.
Claim 3
Dependent Claim
22 words
The process of claim 1 wherein said organic polyisocyanate employed in step (a) is an isomeric mixture of 2,4- and 2,6-toluene diisocyanate.
Claim 4
Dependent Claim
16 words
The process of claim 1 wherein said polyol employed in step (a) is a polyether polyol.
Claim 5
Dependent Claim
21 words
The process of claim 1 wherein the reaction of step (a) is carried out in the presence of a copolymerizable solvent.
Claim 6
Dependent Claim
13 words
The process of claim 4 wherein said copolymerizable solvent is a vinylidene compound.
Claim 7
Dependent Claim
32 words
The process of claim 1 wherein said isocyanate reactive group-containing unsaturated monomer is selected from the group consisting of hydroxyethyl acrylate, hydroxypropyl acrylate, hydroxyethyl methacrylate, hydroxyethyl acrylamide, hydroxypropyl acrylamide and mixtures thereof.
Claim 8
Dependent Claim
31 words
The process of claim 1 wherein said ethylenically unsaturated monomer is selected from the group consisting of styrene, acrylonitrile, vinyl chloride, methyl methacrylate, hydroxyethyl acrylate, butadiene, isoprene, chloroprene, and mixtures thereof.
Claim 9
Dependent Claim
31 words
The process of claim 1 wherein said polyurethane oligomer is employed in step (c) in an amount from about 0.2% to about 15%, based on the weight of total polyol present.
Claim 10
Dependent Claim
32 words
The process of claim 1 wherein said ethylenically unsaturated monomer is employed in step (c) in an amount from about 5% to about 60%, based on the weight of total polyol present.
Claim 11
Dependent Claim
144 words
A process for preparing a graft copolymer comprising: (a) reacting an isomeric mixture of 2,4- and 2,6-toluene diisocyanate with a polyether polyol having an average equivalent weight from about 1000 to about 3000 in an equivalent ratio of NCO to OH from about 1.1/1 to about 1.4/1 to yield an isocyanate-terminated prepolymer; (b) reacting said isocyanate-terminated prepolymer with hydroxyethyl acrylate in sufficient proportions to form a polyurethane oligomer having a final free NCO content from about 0% to about 0.5% by weight and having terminal reactive unsaturation; and (c) copolymerizing said polyurethane oligomer with styrene in the presence of a polyol and in the presence of a catalytically effective amount of a free radical catalyst at a temperature from about 90° C. to about 140° C. to form a dispersion of a graft polymer of said oligomer and said styrene in a polyol medium.
Claim 12
Dependent Claim
144 words
A process for preparing a graft copolymer comprising: (a) reacting an isomeric mixture of 2,4- and 2,6-toluene diisocyanate with a polyether polyol having an average equivalent weight from about 1000 to about 3000 in an equivalent ratio of NCO to OH from about 1.1/1 to about 1.4/1 to yield an isocyanate-terminated prepolymer; (b) reacting said isocyanate-terminated prepolymer with hydroxyethyl acrylate in sufficient proportions to form a polyurethane oligomer having a final free NCO content from about 0% to about 0.5% by weight and having terminal reactive unsaturation; and (c) copolymerizing said polyurethane oligomer with styrene in the presence of a polyol and in the presence of a catalytically effective amount of a free radical catalyst at a temperature from about 90° C. to about 140° C. to form a dispersion of a graft polymer of said oligomer and said styrene in a polyol medium.
Claim 13
Dependent Claim
23 words
The process of claim 10 wherein the reaction of step (a) is carried out in the presence of a copolymerizable solvent comprising styrene.
Claim 14
Dependent Claim
31 words
The process of claim 11 wherein said polyurethane oligomer is employed in step (c) in an amount from about 0.5% to about 5%, based on the weight of total polyol present.
Claim 15
Dependent Claim
29 words
The process of claim 12 wherein said styrene is employed in step (c) in an amount from about 15% to about 40%, based on the weight of polyol present.
Claim 16
Dependent Claim
23 words
The process of claim 13 wherein said polyol used in step (c) is the same as said polyether polyol employed in step (a).
Claim 17
Dependent Claim
18 words
A dispersion of a graft copolymer in a polyol medium as produced by the process of claim 1.
Claim 18
Dependent Claim
11 words
A graft copolymer as produced by the process of claim 1.
Claim 19
Dependent Claim
18 words
A dispersion of a graft copolymer in a polyol medium as produced by the process of claim 10.
Claim 20
Dependent Claim
11 words
A graft copolymer as produced by the process of claim 10.
Claim 21
Dependent Claim
48 words
In a process for preparing a polyurethane composition from a reaction mixture comprising a polyol reactant, an organic polyisocyanate, and a polyurethane-forming catalyst, the improvement wherein said polyol reactant comprises a dispersion of a graft copolymer in a polyol medium prepared according to the process of claim 1.
Claim 22
Dependent Claim
11 words
A polyurethane composition prepared according to the process of claim 19.
Claim 23
Dependent Claim
48 words
In a process for preparing a polyurethane composition from a reaction mixture comprising a polyol reactant, an organic polyisocyanate, and a polyurethane-forming catalyst, the improvement wherein said polyol reactant comprises a dispersion of a graft copolymer in a polyol medium prepared according to the process of claim 10.
Claim 24
Dependent Claim
11 words
A polyurethane composition prepared according to the process of claim 21.
Claim 25
Dependent Claim
51 words
In a process for preparing a polyurethane foam from a reaction mixture comprising a polyol reactant, an organic polyisocyanate, a polyurethane-forming catalyst, and a foaming agent, the improvement wherein said polyol reactant comprises a dispersion of a graft copolymer in a polyol medium prepared according to the process of claim 1.
Claim 26
Dependent Claim
11 words
A polyurethane foam prepared according to the process of claim 23.
Claim 27
Dependent Claim
51 words
In a process for preparing a polyurethane foam from a reaction mixture comprising a polyol reactant, an organic polyisocyanate, a polyurethane-forming catalyst, and a foaming agent, the improvement wherein said polyol reactant comprises a dispersion of a graft copolymer in a polyol medium prepared according to the process of claim 10.
Claim 28
Dependent Claim
11 words
A polyurethane foam prepared according to the process of claim 25.
References Cited (Backward Citations)
US4034017A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1988-06-03 | 1988-12-03 | 1989-06-04 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-06-03 | 1992-12-03 | 1993-06-04 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-06-03 | 1996-12-03 | 1997-06-04 | $7700.00 | Window Closed / Lapsed |