US4159376A
Expired / Lapsed
US
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Isocyanurates from unsaturated monohydric alcohols and polyisocyanates
Assignee: Beazer East Inc
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Filing: 1977-07-27
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Granted: 1979-06-26
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Expires: 1997-07-27
Abstract
Abstract Isocyanurate polymers having improved physical properties are disclosed. Unsaturated isocyanates are prepared by reacting a polyisocyanate with a monohydric alcohol containing a vinylidene group to form an isocyanate-containing urethane and then reacting the isocyanate-containing urethane with tris(2-hydroxyethyl)isocyanurate to form an unsaturated isocyanurate. The unsaturated isocyanurate may be homopolymerized or copolymerized with ethylenically unsaturated compounds to form isocyanurate polymers having an excellent combination of physical properties.
Inventors
- 👤 Erich Kuehn
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 00:24
CPC Classifications
C; C08; C08F; C08F20/00; C08F20/02; C08F20/10; C08F20/34; C08F20/36; C07; C07D; C07D251/00; C07D251/02; C07D251/12; C07D251/26; C07D251/30; C07D251/34
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
68 words
A process for preparing an ethylenically unsaturated isocyanurate which comprises a first step of reacting an aromatic polyisocyanate with a monohydric alcohol containing a vinylidene group and which is selected from the group consisting of hydroxypropyl methacrylate, hydroxypropyl acrylate, hydroxyethyl methacrylate, hydroxyethyl acrylate, or mixtures thereof, to form a monoisocyanate-containing urethane, and a second step of reacting the monoisocyanate-containing urethane with tris(2-hydroxyethyl)isocyanurate to form an ethylenically unsaturated isocyanurate.
Claim 2
Dependent Claim
68 words
A process for preparing an ethylenically unsaturated isocyanurate which comprises a first step of reacting an aromatic polyisocyanate with a monohydric alcohol containing a vinylidene group and which is selected from the group consisting of hydroxypropyl methacrylate, hydroxypropyl acrylate, hydroxyethyl methacrylate, hydroxyethyl acrylate, or mixtures thereof, to form a monoisocyanate-containing urethane, and a second step of reacting the monoisocyanate-containing urethane with tris(2-hydroxyethyl)isocyanurate to form an ethylenically unsaturated isocyanurate.
Claim 3
Dependent Claim
39 words
A process of claim 1 wherein the reaction in the first step and the reaction in the second step are conducted in the presence of a solvent which is unreactive with isocyanate groups and which contains a vinylidene group.
Claim 4
Dependent Claim
16 words
A process of claim 1 wherein the aromatic isocyanate is tolylene diisocyanate or diphenyl methane polyisocyanate.
Claim 5
Dependent Claim
116 words
A process of claim 1 which comprises (a) preparing a solution of a monohydric alcohol containing a vinylidene group and an inhibitor of vinyl polymerization in a solvent which is unreactive with isocyanate groups, (b) slowly adding an organic polyisocyanate to the solution to furnish an NCO/OH ratio of about 2 and in the presence of sufficient oxygen to keep the inhibitor active and while maintaining the temperature of the solution from about 40° C. to about 85° C. to form a monoisocyanate-containing urethane, (c) adding about one mol of tris(2-hydroxyethyl)isocyanurate to about three mols of the monoisocyanate-containing urethane and maintaining the temperature at from 60° C. to 110° C. to form an ethylenically unsaturated isocyanurate.
Claim 6
Dependent Claim
25 words
A process of claim 4 wherein the organic isocyanate is an aromatic isocyanate and the monohydric alcohol is hydroxypropylmethacrylate, hydroxypropylacrylate, hydroxyethylmethacrylate, hydroxyethylacrylate, or mixtures thereof.
Claim 7
Dependent Claim
11 words
A process of claim 5 wherein the isocyanate is tolylene diisocyanate.
Claim 8
Dependent Claim
12 words
A process of claim 4 wherein the solvent is a vinylidene monomer.
Claim 9
Dependent Claim
23 words
A process of claim 4 wherein the solvent is selected from the group consisting of styrene, methylmethacrylate, divinylbenzene, ethylmethacrylate, ethylacrylate, and mixtures thereof.
Claim 10
Dependent Claim
59 words
A process of claim 4 wherein the ratio of the combined weight of monohydric alcohol and polyisocyanate to weight of solvent used in the formation of the isocyanate-containing urethane is from about 0.33 to about 9.00 and the weight ratio of the combined weight of monoisocyanate-containing urethane and tris(2-hydroxyethyl)isocyanurate to solvent used is from about 0.33 to about 2.33.
Claim 11
Dependent Claim
62 words
An ethylenically unsaturated isocyanurate characterized by the formula; ##STR4## wherein R is a monovalent radical obtained by removing the hydroxyl group from the hydroxypropyl methacrylate, hydroxyethyl methacrylate, hydroxyethyl acrylate or hydroxypropyl acrylate and R' is a divalent organic radical free of a group which is reactive with an isocyanate group and is obtained by removing two isocyanate groups from an aromatic diisocyanate.
Claim 12
Dependent Claim
62 words
An ethylenically unsaturated isocyanurate characterized by the formula; ##STR4## wherein R is a monovalent radical obtained by removing the hydroxyl group from the hydroxypropyl methacrylate, hydroxyethyl methacrylate, hydroxyethyl acrylate or hydroxypropyl acrylate and R' is a divalent organic radical free of a group which is reactive with an isocyanate group and is obtained by removing two isocyanate groups from an aromatic diisocyanate.
Claim 13
Dependent Claim
11 words
An ethylenically unsaturated isocyanurate of claim 10 wherein R' is tolylyl.
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) | 1982-06-25 | 1982-12-25 | 1983-06-26 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-06-25 | 1986-12-25 | 1987-06-26 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-06-25 | 1990-12-25 | 1991-06-26 | $7700.00 | Window Closed / Lapsed |