US4335219A
Expired / Lapsed
US
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Process for reacting isocyanates in the presence of quaternary ammonium zwitterions
Assignee: Dow Chemical Co
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Filing: 1981-04-06
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Granted: 1982-06-15
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Expires: 2001-04-06
Abstract
Abstract The reaction of an isocyanate such as toluene diisocyanate with itself to form an isocyanurate or with an active hydrogen compound such as diethylene glycol to form a urethane is catalyzed by the presence of an ar-ammonium areneoxide such as 4-dodecyl-2-trimethylammonium phenoxide.
Inventors
- 👤 Donald H. Clarke
- 👤 George J. Pomranky
- 👤 Donald L. Schmidt
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 21:34
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/02; C08G18/022; C08G18/06; C08G18/08; C08G18/16; C08G18/18; C08G18/1875
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
59 words
A process for reacting an organic isocyanate with itself or another organic isocyanate which process comprises contacting an organic isocyanate or a mixture of organic isocyanates with an ar-ammonium zwitterion which is soluble in the isocyanate under conditions such that the ammonium zwitterion initiates the reaction of the isocyanate moieties of the organic isocyanate or mixture of organic isocyanates.
Claim 2
Dependent Claim
59 words
A process for reacting an organic isocyanate with itself or another organic isocyanate which process comprises contacting an organic isocyanate or a mixture of organic isocyanates with an ar-ammonium zwitterion which is soluble in the isocyanate under conditions such that the ammonium zwitterion initiates the reaction of the isocyanate moieties of the organic isocyanate or mixture of organic isocyanates.
Claim 3
Dependent Claim
14 words
The process of claim 1 wherein the isocyanate moieties react to form isocyanurate moieties.
Claim 4
Dependent Claim
54 words
A process for reacting an organic isocyanate with an active hydrogen compound which process comprises contacting the isocyanate with the active hydrogen compound in the presence of an ar-ammonium zwitterion, which is soluble in the isocyanate under conditions such that the ammonium zwitterion catalyzes the reaction of the active hydrogen compound with the isocyanate.
Claim 5
Dependent Claim
54 words
A process for reacting an organic isocyanate with an active hydrogen compound which process comprises contacting the isocyanate with the active hydrogen compound in the presence of an ar-ammonium zwitterion, which is soluble in the isocyanate under conditions such that the ammonium zwitterion catalyzes the reaction of the active hydrogen compound with the isocyanate.
Claim 6
Dependent Claim
26 words
A process of claim 2 or 3 wherein the ammonium zwitterion is characterized by an aromatic ring bearing an oxygen anion and a quaternary ammonium group.
Claim 7
Dependent Claim
21 words
The process of claim 4 wherein the aromatic ring also bears a monovalent organic radical having at least one carbon atom.
Claim 8
Dependent Claim
115 words
The process of claim 5 wherein the ammonium zwitterion is represented by one of the formulae: ##STR17## wherein each Ar is independently a cyclic aromatic polyyl; each R 1 is independently a suitably inert monovalent radical capable of existing as a substituent on Ar provided that at least one R 1 is an organic radical containing at least four carbon atoms; each Z is independently a suitably inert divalent radical capable of bridging aromatic moieties such as Ar; each R 2 is independently a suitably inert monovalent radical and/or two or three of R 2 are collectively a suitably inert divalent or trivalent organic radical capable of forming a heterocyclic ring with N + .
Claim 9
Dependent Claim
39 words
The process of claim 6 wherein the ammonium zwitterion is represented by the formula: ##STR18## wherein R 1 is alkyl having from 4 to 20 carbons and each R 2 is individually alkyl having from 1 to 10 carbons.
Claim 10
Dependent Claim
11 words
The process of claim 7 wherein the ammonium zwitterion is ##STR19##
Claim 11
Dependent Claim
44 words
The process of claim 2 or 3 wherein the organic isocyanate is an organic polyisocyanate represented by the formula R(NCO) z wherein R is a polyvalent organic radical and z is an integer of 2 or more that corresponds to the valence of R.
Claim 12
Dependent Claim
14 words
The process of claim 7 wherein the organic isocyanate is a polymethylene polyphenyl isocyanate.
Claim 13
Dependent Claim
24 words
The process of claim 3 wherein the active hydrogen compound is a polyol and the isocyanate reacts with the polyol to form urethane moieties.
Claim 14
Dependent Claim
16 words
A polyurethane formulation comprising a polyol, an organic polyisocyanate and the ammonium zwitterion of claim 1.
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) | 1985-06-14 | 1985-12-14 | 1986-06-15 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-06-14 | 1989-12-14 | 1990-06-15 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-06-14 | 1993-12-14 | 1994-06-15 | $7700.00 | Window Closed / Lapsed |