US5087690A
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Hybrid amino resin compositions
Assignee: Solutia Inc
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Filing: 1989-01-24
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Granted: 1992-02-11
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Expires: 2009-01-24
Abstract
Abstract Hybrid curable compositions comprising components curable by condensation, and components curable by free-radical initiated polymerization, cure being catalyzed by a metal sulfonate. The components curable by condensation comprise amino resins and co-reactants. The components curable by free radical initiated polymerization comprise acryloyl compounds and allylic or vinylenearylenemethylidyne compounds.
Inventors
- 👤 David W. Demarey
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 12:50
CPC Classifications
C; C08; C08G; C08G12/00; C08G12/02; C08G12/40
Claims Analysis
Total Claims: 28
Claim 1
Independent Claim
52 words
A curable composition comprising an alkoxymethyl amino resin component, a hydroxy-functional component co-reactive with the alkoxymethyl amino resin, a (meth)-acryloyl component, an allylic or vinylenearylenemethylidyne component and a metal sulfonate of a metal selected from Groups IB, IIIB, IVB, VB, VIB, VIIB, and VIII of the CAS version of the Periodic Table.
Claim 2
Dependent Claim
52 words
A curable composition comprising an alkoxymethyl amino resin component, a hydroxy-functional component co-reactive with the alkoxymethyl amino resin, a (meth)-acryloyl component, an allylic or vinylenearylenemethylidyne component and a metal sulfonate of a metal selected from Groups IB, IIIB, IVB, VB, VIB, VIIB, and VIII of the CAS version of the Periodic Table.
Claim 3
Dependent Claim
107 words
The composition of claim 1 which contains, per 100 parts by weight of the components, from about 0.03 to about 0.50 equivalents of alkoxymethylamino groups, from about 0.03 to about 0.30 equivalents of functional groups co-reactive with the alkoxymethylamino groups, from about 0.08 to about 0.60 equivalents of (meth)-acryloyl groups and from about 0.02 to about 0.30 equivalents of allylic or vinylenearylenemethylidyne groups, the ratio of functional groups co-reactive with the alkoxymethylamino groups to alkoxymethylamino groups being in the range of about 0.20 to about 3.0, and the ratio of allylic or vinylenearylenemethylidyne groups to (meth)-acryloyl groups being in the range of about 0.2 to about 1.5.
Claim 4
Dependent Claim
21 words
The composition of claim 1 wherein the metal is selected from the group consisting of vanadium, manganese, cobalt, nickel and niobium.
Claim 5
Dependent Claim
19 words
The composition of claim 1 wherein the metal is selected from the group consisting of vanadium, manganese and niobium.
Claim 6
Dependent Claim
24 words
The composition of claim 1 wherein the metal sulfonate is the salt of a sulfonic acid containing C 6 to C 12 aliphatic radicals.
Claim 7
Dependent Claim
38 words
The composition of claim 1 wherein the metal sulfonate is the salt of a sulfonic acid selected from the group consisting of hexanesulfonic acid, dodecanesulfonic acid, hexylbenzenesulfonic acid, dodecylbenzenesulfonic acid, dodecylnaphthalenesulfonic acid, dinonylnaphthalenesulfonic acid and dinonylnaphthalene disulfonic acid.
Claim 8
Dependent Claim
12 words
The composition of claim 1 additionally comprising a blocked sulfonic acid catalyst.
Claim 9
Dependent Claim
33 words
The composition of claim 1 additionally comprising a ligand for the metal ion of the metal sulfonate, of the type that can form metal complexes of various oxidation states of the metal ion.
Claim 10
Dependent Claim
12 words
The composition of claim 8 wherein the ligand is 2,2'-bipyridine or 1,10-phenanthroline.
Claim 11
Dependent Claim
11 words
The composition of claim 1 additionally comprising a free-radical generating compound.
Claim 12
Dependent Claim
35 words
The composition of claim 10 wherein the free-radical generating compound is selected from the group consisting of t-butyl hydroperoxide, cumene hydroperoxide, cumene peroxide, methyl ethyl ketone peroxide, lauroyl peroxide, benzoyl peroxide, 2,5-dihydroperoxy-2,5-dimethylhexane and azo-bis (isobutyronitrile).
Claim 13
Dependent Claim
168 words
The composition of claim 2 wherein the (meth)-acryloyl composition is represented by the formula: ##STR7## where R 4 is selected from the group consisting of H, CH 3 and C 2 H 5 where r is an integer in the range of 1 to 10 and Z is a saturated or ethylenically unsaturated residue of an alcohol, a polyol, a carboxylic acid, a poly-carboxylic acid, an amine, a polyamine, an aminotriazine, an epoxide, a polyepoxide, an isocyanate or a polyisocyanate of a number average molecular weight less than about 4000 containing a hydrocarbon, ester, amide, ether, urethane or triazine nucleus, wherein the allylic component has an unsaturation equivalency of less than 300, a number average molecular weight of less than 10,000 and has from 1 to 60 allylic groups per molecule; and wherein the metal of the metal sulfonate is selected from the group consisting of vanadium, manganese, cobalt, nickel, copper and niobium and is present in a heat-activatable, catalytically effective amount to effect cure of the composition.
Claim 14
Dependent Claim
51 words
The curable composition of claim 6 wherein r is at least 2 and the allylic component has a number average molecular weight in the range of about 200 to 4000, and has at least two allylic groups per molecule, and wherein the allylic group is allyloxy (CH 2 ═CH--CH 2 --O).
Claim 15
Dependent Claim
38 words
The composition of claim 13 wherein the metal is selected from the group consisting of vanadium, manganese and niobium and the metal sulfonate is the salt of a sulfonic acid containing C 6 to C 12 aliphatic radicals.
Claim 16
Dependent Claim
18 words
The composition of claim 13 additionally comprising a blocked sulfonic acid catalyst present in a heat-activatable cure-rate-enhancing amount.
Claim 17
Dependent Claim
33 words
The composition of claim 13 additionally comprising a ligand for the metal ion of the metal sulfonate, of the type that can form metal complexes of various oxidation states of the metal ion.
Claim 18
Dependent Claim
11 words
The composition of claim 13 additionally comprising a free-radical generating compound.
Claim 19
Dependent Claim
121 words
The composition of claim 13 wherein the alkoxymethyl amino resin is an alkoxymethyl urea or an alkoxymethyl aminotriazine of average degree of condensation of about 5 or less, containing at least 1.8 alkoxymethyl groups per molecule, derived from a urea, or an aminotriazine, formaldehyde and a C1 to C8 alcohol, wherein the urea: formaldehyde: alcohol ratio is from about 1:1.5:1.25 to 1:4:4 and wherein the aminotriazine:formaldehyde: alcohol ratio is from about 1:2n-3:2n-3.5 to 1:2n : 2n where n is the number of amino groups per triazine ring, and wherein the functional co-reactant is a poly-functional resin of number average molecular weight in the range of from about 300 to about 4000 selected from the group consisting of poly(meth)acrylates, alkyds and polyesters.
Claim 20
Dependent Claim
15 words
The curable composition of claim 18 wherein the alkoxymethyl amino resin is an alkoxymethyl melamine.
Claim 21
Dependent Claim
6 words
The cured composition of claim 1.
Claim 22
Dependent Claim
6 words
The cured composition of claim 12.
Claim 23
Dependent Claim
6 words
The cured composition of claim 18.
Claim 24
Dependent Claim
6 words
The cured composition of claim 19.
Claim 25
Dependent Claim
180 words
The composition of claim 13 wherein the allylic component is represented by the structural formula: R.sub.5 ((E).sub.m R.sub.6).sub.n where R 5 is a radical of molecular weight less than about 15,000 obtained by removal of active hydrogen from an active hydrogen compound selected from the group consisting of water, alcohols, thiols, carboxylic acids, carboxylic amides and amines, where the functionality of R 5 is n and is in the range of 1 to 10, where E is a divalent radical selected from the group represented by the formula ##STR8## where the X groups are independently selected from the group consisting of H, CH 3 , C 2 H 5 and CH 2 OCH 2 Y, Y being selected from the group consisting of CH═CH 2 , H 3 C--C═CH 2 , H 5 C 2 --C═CH 2 , and P--C 6 H 4 CH═CH 2 where R 6 is hydrogen or an unsubstituted or substituted C 1 to C 10 hydrocarbyl radical, and where the product of m and n is at least 4 and not more than about 60.
Claim 26
Dependent Claim
21 words
The curable composition of claim 19 wherein the alkoxymethyl groups are selected from the group consisting of methoxymethyl, butoxymethyl and iso-butoxymethyl.
Claim 27
Dependent Claim
6 words
The cured composition of claim 13.
Claim 28
Dependent Claim
6 words
The cured composition of claim 24.
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1995-02-10 | 1995-08-12 | 1996-02-11 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1999-02-10 | 1999-08-12 | 2000-02-11 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2003-02-10 | 2003-08-12 | 2004-02-11 | $7700.00 | Window Closed / Lapsed |