US4540781A
Expired / Lapsed
US
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Product and process trimerization of organic isocyanates
Assignee: Dow Chemical Co
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Filing: 1983-08-11
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Granted: 1985-09-10
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Expires: 2003-08-11
Abstract
Abstract Disclosed is a method for the trimerization of organic isocyanates comprising thermally activating, in the presence of said isocyanates, a catalyst comprising a carboxylic acid salt selected from the alkali metal salts or quaternary ammonium salts of particular substituted malonic acids or half-esters thereof, particular carbamyl substituted aliphatic acids, or triaryl acetic acids. Mixtures of the catalysts with isocyanates have surprisingly long periods of stability at ambient temperatures (about 20° C.) which makes the present method particularly suitable to systems for molding polyiso-cyanurates wherein long open times are required of a resin pre-mix prior to the actual curing step.
Inventors
- 👤 Edward A. Barsa
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 17:48
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/08; C08G18/16; C08G18/18; C08G18/1875; C08G18/02; C08G18/022; C08G18/22; C08G18/225; C08G2115/00; C08G2115/02
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
234 words
A method for the trimerization of an organic isocyanate comprising thermally activating at a temperature of from about 50° C. to about 200° C. in the presence of said isocyanate a catalyst otherwise having an induction period greater than one hour for initiating said trimerization at about 20° C. said catalyst consisting essentially of a compound selected from the group consisting of the following formulae ##STR9## wherein R 1 in (I) is alkyl having 2 to 8 carbon atoms, inclusive, and each R 1 in (II) is independently selected from alkyl having 2 to 8 carbon atoms, inclusive, R 2 is a highly branched alkyl having 3 to 8 carbon atoms, inclusive, R 3 is selected from the group consisting of hydrogen, alkyl, and aryl, R 4 is selected from the group consisting of alkyl, aryl, aralkyl, and cycloalkyl, each R 5 is independently selected from aryl, and M.sup.⊕ is a cation selected from the group consisting of alkali metal cations and quaternary ammonium cations having the formula .sup.⊕ N(R 6 ) 4 wherein each of the four R 6 radicals is independently selected from the group consisting of alkyl, aralkyl, cycloalkyl, and radicals having the formula ##STR10## wherein R 7 is selected from the group consisting of hydrogen and methyl and n is a number of from 1 to 4 provided that no more than one R 6 radical has the formula (IV).
Claim 2
Independent Claim
234 words
A method for the trimerization of an organic isocyanate comprising thermally activating at a temperature of from about 50° C. to about 200° C. in the presence of said isocyanate a catalyst otherwise having an induction period greater than one hour for initiating said trimerization at about 20° C. said catalyst consisting essentially of a compound selected from the group consisting of the following formulae ##STR9## wherein R 1 in (I) is alkyl having 2 to 8 carbon atoms, inclusive, and each R 1 in (II) is independently selected from alkyl having 2 to 8 carbon atoms, inclusive, R 2 is a highly branched alkyl having 3 to 8 carbon atoms, inclusive, R 3 is selected from the group consisting of hydrogen, alkyl, and aryl, R 4 is selected from the group consisting of alkyl, aryl, aralkyl, and cycloalkyl, each R 5 is independently selected from aryl, and M.sup.⊕ is a cation selected from the group consisting of alkali metal cations and quaternary ammonium cations having the formula .sup.⊕ N(R 6 ) 4 wherein each of the four R 6 radicals is independently selected from the group consisting of alkyl, aralkyl, cycloalkyl, and radicals having the formula ##STR10## wherein R 7 is selected from the group consisting of hydrogen and methyl and n is a number of from 1 to 4 provided that no more than one R 6 radical has the formula (IV).
Claim 3
Dependent Claim
13 words
A method according to claim 1 wherein said compound has the formula (I).
Claim 4
Dependent Claim
13 words
A method according to claim 2 wherein said compound has the formula ##STR11##
Claim 5
Dependent Claim
13 words
A method according to claim 1 wherein said compound has the formula (II).
Claim 6
Dependent Claim
13 words
A method according to claim 4 wherein said compound has the formula ##STR12##
Claim 7
Dependent Claim
13 words
A method according to claim 4 wherein said compound has the formula ##STR13##
Claim 8
Dependent Claim
13 words
A method according to claim 4 wherein said compound has the formula ##STR14##
Claim 9
Dependent Claim
13 words
A method according to claim 1 wherein said compound has the formula (III).
Claim 10
Dependent Claim
13 words
A method according to claim 8 wherein said compound has the formula ##STR15##
Claim 11
Dependent Claim
13 words
A method according to claim 1 wherein said isocyanate is an aromatic polyisocyanate.
Claim 12
Dependent Claim
18 words
A method according to claim 10 wherein said isocyanate is trimerized in the presence of an organic polyol.
Claim 13
Dependent Claim
51 words
A method for the trimerization of an aromatic polyisocyanate in the presence of an organic polyol comprising heating said polyisocyanate and said polyol at a temperature of from about 50° C. to about 200° C. in the presence of a catalyst consisting essentially of a compound in accordance with claim 1.
Claim 14
Dependent Claim
13 words
A method according to claim 12 wherein said compound has the formula ##STR16##
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1988-09-09 | 1989-03-11 | 1989-09-10 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-09-09 | 1993-03-11 | 1993-09-10 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-09-09 | 1997-03-11 | 1997-09-10 | $7700.00 | Window Closed / Lapsed |