US4265798A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Isocyanurate products and polyurethanes therefrom
Assignee: Uniroyal Ltd Canada
•
Filing: 1980-02-11
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Granted: 1981-05-05
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Expires: 2000-02-11
Abstract
Abstract Potassium salt of 2-pyrrolidinone is used as a catalyst to cyclotrimerize an organic diisocyanate, yielding a mixture of monomeric cyclotrimerized product (isocyanurate) and oligomers thereof, soluble in common organic solvents and vinyl monomers. The catalyst can be used to make one-shot isocyanurate-crosslinked polyurethanes. Prepolymers and moisture-curing coating compositions can also be prepared.
Inventors
- 👤 Anupama Mishra
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 00:16
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/28; C08G18/40; C08G18/63; C08G18/637; C08G18/08; C08G18/16; C08G18/22; C08G18/225; C08G18/70; C08G18/72; C08G18/77; C08G18/78; C08G18/79; C08G18/791; C08G2115/00; C08G2115/02; Y; Y10; Y10T; Y10T428/00; Y10T428/31504; Y10T428/31547; Y10T428/31551
Claims Analysis
Total Claims: 26
Claim 1
Independent Claim
41 words
A method of cyclotrimerizing an organic diisocyanate comprising contacting the organic diisocyanate with a small but effective amount of potassium salt of 2-pyrrolidinone as a cyclotrimerization catalyst, whereby the organic diisocyanate is cyclotrimerized to an isocyanurate-containing product soluble in organic solvents.
Claim 2
Independent Claim
41 words
A method of cyclotrimerizing an organic diisocyanate comprising contacting the organic diisocyanate with a small but effective amount of potassium salt of 2-pyrrolidinone as a cyclotrimerization catalyst, whereby the organic diisocyanate is cyclotrimerized to an isocyanurate-containing product soluble in organic solvents.
Claim 3
Dependent Claim
25 words
A method as in claim 1 in which the organic diisocyanate is selected from the group consisting of toluene diisocyanate, methylene diphenylisocyanate and isophorone diisocyanate.
Claim 4
Dependent Claim
14 words
A method as in claim 1 carried out in an inert organic solvent medium.
Claim 5
Dependent Claim
17 words
A method as in claim 1 carried out in an excess of the diisocyanate as the medium.
Claim 6
Dependent Claim
18 words
A method as in claim 1 in which the product contains a mixture of monomeric and oligomeric isocyanurates.
Claim 7
Dependent Claim
35 words
A method as in claim 1 in which the reaction mixture is agitated under an inert atmosphere at a temperature between 20° C. and 150° C., for a period of from 1/2 to 24 hours.
Claim 8
Dependent Claim
20 words
A method as in claim 1 in which the cyclotrimerization reaction is quenched by the addition of an acylating agent.
Claim 9
Dependent Claim
9 words
The product obtained by the method of claim 1.
Claim 10
Dependent Claim
15 words
A solution of the product of claim 1 in an excess of the starting diisocyanate.
Claim 11
Independent Claim
23 words
A method of making an isocyanurate-crosslinked polyurethane comprising mixing a diol, an organic diisocyanate and a catalytic amount of potassium salt of 2-pyrrolidinone.
Claim 12
Independent Claim
23 words
A method of making an isocyanurate-crosslinked polyurethane comprising mixing a diol, an organic diisocyanate and a catalytic amount of potassium salt of 2-pyrrolidinone.
Claim 13
Dependent Claim
8 words
The product of the method of claim 10.
Claim 14
Dependent Claim
7 words
A non-cellular product as in claim 11.
Claim 15
Dependent Claim
13 words
A solution of the product of claim 1 in a liquid vinyl monomer.
Claim 16
Dependent Claim
51 words
A method of making a thermoset polymer comprising mixing (a) a solution of the product of claim 1 in a vinyl monomer, (b) a diol, (c) a peroxide curative, and (d) a catalyst for the reaction between --NCO and --OH to form polyurethane, and thereafter subjecting the mixture to curing conditions.
Claim 17
Dependent Claim
8 words
The product of the method of claim 14.
Claim 18
Dependent Claim
7 words
A non-cellular product as in claim 15.
Claim 19
Dependent Claim
23 words
A method of making a urethane prepolymer comprising mixing a polymeric diol with the product of claim 1 in the absence of moisture.
Claim 20
Dependent Claim
9 words
A prepolymer produced by the method of claim 17.
Claim 21
Dependent Claim
30 words
A method of making a cured polyurethane elastomer comprising providing a prepolymer as in claim 18, mixing the prepolymer with a polyurethane curative, and subjecting the mixture to curing conditions.
Claim 22
Dependent Claim
8 words
The product of the method of claim 19.
Claim 23
Dependent Claim
7 words
A non-cellular product as in claim 20.
Claim 24
Dependent Claim
21 words
A coating composition comprising the product of claim 1, a diol, and a polyurethane catalyst, dissolved in an inert organic solvent.
Claim 25
Dependent Claim
34 words
A method of coating a substrate comprising providing the coating composition of claim 22, applying said composition to the substrate, volatilizing the solvent, and curing the thus-deposited coating by the action of atmospheric moisture.
Claim 26
Dependent Claim
10 words
The coated substrate resulting from the method of claim 23.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-05-04 | 1984-11-03 | 1985-05-05 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-05-04 | 1988-11-03 | 1989-05-05 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-05-04 | 1992-11-03 | 1993-05-05 | $7700.00 | Window Closed / Lapsed |