US4128537A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Process for preparing ethylenically unsaturated isocyanurates
Assignee: Beazer East Inc
•
Filing: 1977-07-27
•
Granted: 1978-12-05
•
Expires: 1997-07-27
Abstract
Abstract Process for the preparation of ethylenically unsaturated isocyanurates comprising reacting polyisocyanate with a monohydric alcohol containing a vinylidene group in the presence of a copper salt to form an isocyanate-containing urethane and then trimerizing the isocyanate-containing urethane to form an ethylenically unsaturated isocyanurate. The ethylenically unsaturated isocyanurate may be homopolymerized or copolymerized with ethylenically unsaturated monomers to form high molecular weight polymers having excellent physical properties.
Inventors
- 👤 Kenneth H. Markiewitz
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 12:56
CPC Classifications
C; C07; C07D; C07D251/00; C07D251/02; C07D251/12; C07D251/26; C07D251/30; C07D251/34; C08; C08F; C08F120/00; C08F120/02; C08F120/10; C08F120/34; C08F120/36
Claims Analysis
Total Claims: 32
Claim 1
Independent Claim
103 words
A process for preparing an ethylenically unsaturated isocyanurate which comprises reacting a polyisocyanate with a monohydric alcohol which contains a vinylidene group and which does not contain an allyl group, in the presence of a copper salt to form an isocyanate-containing urethane, wherein the amounts of monohydric alcohol and polyisocyanate are selected to furnish after said reaction from 0.75 to 1.6 moles of unreacted isocyanate groups per mole of polyisocyanate used, then adding a catalytic amount of an isocyanate trimerization catalyst which will initiate trimerization of the isocyanate-containing urethane without causing gellation, and trimerizing the isocyanate-containing urethane to form an ethylenically unsaturated isocyanurate.
Claim 2
Dependent Claim
103 words
A process for preparing an ethylenically unsaturated isocyanurate which comprises reacting a polyisocyanate with a monohydric alcohol which contains a vinylidene group and which does not contain an allyl group, in the presence of a copper salt to form an isocyanate-containing urethane, wherein the amounts of monohydric alcohol and polyisocyanate are selected to furnish after said reaction from 0.75 to 1.6 moles of unreacted isocyanate groups per mole of polyisocyanate used, then adding a catalytic amount of an isocyanate trimerization catalyst which will initiate trimerization of the isocyanate-containing urethane without causing gellation, and trimerizing the isocyanate-containing urethane to form an ethylenically unsaturated isocyanurate.
Claim 3
Dependent Claim
13 words
A process of claim 1 wherein the organic polyisocyanate is an aromatic polyisocyanate.
Claim 4
Dependent Claim
25 words
A process of claim 2 wherein the monohydric alcohol is hydroxypropyl methacrylate, hydroxypropyl acrylate, hydroxyethyl methacrylate, hydroxyethyl acrylate, pentaerythritol triacrylate, pentaerythritol trimethacrylate, or mixtures thereof.
Claim 5
Dependent Claim
12 words
A process of claim 3 wherein the aromatic isocyanate is tolylene diisocyanate.
Claim 6
Dependent Claim
12 words
A process of claim 4 wherein the copper salt is cupric acetate.
Claim 7
Dependent Claim
116 words
A process of claim 1 which comprises (a) preparing a solution of a copper salt, a free radical polymerization inhibitor, and a monohydric alcohol, said alcohol containing a vinylidene group, in a solvent which is unreactive with isocyanate groups, (b) slowly adding a trimerizable organic polyisocyanate to the solution in the presence of sufficient oxygen to keep the inhibitor active and while maintaining the temperature of the solution from 10° C. to 130° C. to form an isocyanate-containing monourethane, (c) adding a catalytic amount of a trimerization catalyst which will initiate trimerization of the monourethane without causing gellation of the monourethane, and (d) maintaining the temperature from 0° C. to 95° C. to form an isocyanurate.
Claim 8
Dependent Claim
13 words
A process of claim 6 wherein the organic polyisocyanate is an aromatic diisocyanate.
Claim 9
Dependent Claim
13 words
A process of claim 6 wherein the organic polyisocyanate is a tolylene diisocyanate.
Claim 10
Dependent Claim
11 words
A process of claim 7 wherein the alcohol is hydroxypropyl methacrylate.
Claim 11
Dependent Claim
11 words
A process of claim 7 wherein the alcohol is hydroxyethyl methacrylate.
Claim 12
Dependent Claim
11 words
A process of claim 7 wherein the alcohol is hydroxyethyl acrylate.
Claim 13
Dependent Claim
12 words
A process of claim 7 wherein the monohydric alcohol is hydroxypropyl acrylate.
Claim 14
Dependent Claim
17 words
A process of claim 7 wherein the alcohol is a mixture of hydroxypropyl methacrylate and hydroxyethyl methacrylate.
Claim 15
Dependent Claim
12 words
A process of claim 7 wherein the solvent is an aromatic hydrocarbon.
Claim 16
Dependent Claim
12 words
A process of claim 7 wherein the solvent is a vinylidene monomer.
Claim 17
Dependent Claim
31 words
A process of claim 7 wherein the solvent is selected from the group consisting of styrene, benzene, methyl methacrylate, divinylbenzene, ethyl methacrylate, dioxane, ethyl acrylate, ethyl acetate, and methyl ethyl ketone.
Claim 18
Dependent Claim
12 words
A process of claim 7 wherein the trimerization catalyst is tributyl phosphine.
Claim 19
Dependent Claim
12 words
A process of claim 7 wherein the trimerization catalyst is N-benzyltrimethylammonium hydroxide.
Claim 20
Dependent Claim
16 words
A process of claim 7 wherein the trimerization temperature is from 20° C. to 65° C.
Claim 21
Dependent Claim
26 words
A process of claim 7 wherein the amount of solvent is from about 30% to about 80% by weight of the weight of the total composition.
Claim 22
Dependent Claim
12 words
A process of claim 7 wherein the copper salt is cupric acetate.
Claim 23
Dependent Claim
60 words
A process of claim 20 wherein the monohydric alcohol is selected from the group consisting of hydroxypropyl methacrylate, hydroxyethyl methacrylate, hydroxyethyl acrylate, hydroxypropyl acrylate, and mixtures thereof, the solvent is styrene, the polyisocyanate is a tolylene diisocyanate, the copper salt is cupric acetate, the trimerization catalyst is N-benzyltrimethylammonium hydroxide, and the trimerization temperature is from 20° C. to 65° C.
Claim 24
Dependent Claim
17 words
A process of claim 22 wherein the monohydric alcohol is hyroxypropyl methacrylate, hydroxyethyl methacrylate or mixtures thereof.
Claim 25
Dependent Claim
23 words
A process of claim 23 wherein the free radical polymerization inhibitor is hydroquinone, tertiary butyl catechol, monomethyl ether or hydroquinone, or mixtures thereof.
Claim 26
Dependent Claim
22 words
A process of claim 1 wherein the trimerization catalyst is neutralized with an acid after the formation of the ethylenically unsaturated isocyanurate.
Claim 27
Dependent Claim
19 words
A process of claim 25 wherein the acid is methanesulfonic or a mixture of methanesulfonic acid and oxalic acid.
Claim 28
Dependent Claim
23 words
A process of claim 25 wherein a low molecular weight alcohol or secondary amine is added prior to the addition of the acid.
Claim 29
Dependent Claim
13 words
A process of claim 3 wherein the copper salt is a cupric salt.
Claim 30
Dependent Claim
13 words
A process of claim 3 wherein the copper salt is a cuprous salt.
Claim 31
Dependent Claim
22 words
A process of claim 3 wherein the urethane forming reaction and the trimerization reaction are conducted in the absence of a solvent.
Claim 32
Dependent Claim
13 words
A process of claim 1 wherein the monohydric alcohol contains an ester group.
References Cited (Backward Citations)
US2894950A
Cited
GB629015A
Cited
US3840618A
Cited
US2952665A
Cited
GB809809A
Cited
US2947736A
Cited
US3041313A
Cited
US3065231A
Cited
US2958704A
Cited
US3061591A
Cited
US3252942A
Cited
US3168483A
Cited
US3297745A
Cited
US3154522A
Cited
US3437500A
Cited
US3450648A
Cited
US3763269A
Cited
US3609149A
Cited
US3872035A
Cited
US3658801A
Cited
US3850770A
Cited
US3719638A
Cited
US3943075A
Cited
US3642943A
Cited
US3694415A
Cited
US3849349A
Cited
US3821098A
Cited
US3852220A
Cited
US3876728A
Cited
US3723367A
Cited
US3786030A
Cited
US3926875A
Cited
US3914335A
Cited
US3884917A
Cited
US3925335A
Cited
BE816888A
Cited
US3821067A
Cited
US3860673A
Cited
US3932401A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-12-04 | 1982-06-05 | 1982-12-05 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-12-04 | 1986-06-05 | 1986-12-05 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-12-04 | 1990-06-05 | 1990-12-05 | $7700.00 | Window Closed / Lapsed |