US4200729A
Expired / Lapsed
US
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Curing amino resins with aromatic sulfonic acid oxa-azacyclopentane adducts
Assignee: King Industries Inc
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Filing: 1978-05-22
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Granted: 1980-04-29
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Expires: 1998-05-22
Abstract
Abstract Amino resins, e.g., urea-formaldehyde and melamine-formaldehyde thermosetting resin systems, are cured with thermally-decomposable adducts of aromatic sulfonic acids and oxa-azacyclopentanes. The resin products cured with these adducts provide surface coatings having superior water resistance properties. The cured compositions can include other conventional ingredients capable of co-reacting with the amino resins, such as polyols, polyacids, alkyd resins, polyester resins, epoxies, acrylics and the like, to provide compositions curable to products having a wide range of properties.
Inventors
- 👤 Leonard J. Calbo
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 21:11
CPC Classifications
C; C07; C07D; C07D263/00; C07D263/02; C07D263/04; C08; C08K; C08K5/00; C08K5/36; C08K5/41; C08K5/42; Y; Y10; Y10T; Y10T428/00; Y10T428/31504; Y10T428/31551; Y10T428/31627; Y10T428/31678; Y10T428/31688; Y10T428/31942; Y10T428/31949; Y10T428/31957
Claims Analysis
Total Claims: 28
Claim 1
Independent Claim
149 words
A composition comprising a convertible amino resin selected from the group consisting of amino- or imino-group containing compounds condensed with an aldehyde, dialdehyde and aldehyde precursor and a catalytically effective amount of a thermally-decomposable adduct of an aromatic sulfonic acid, said adduct being of the general formula: ##STR3## wherein A is phenyl or naphthyl and x is a whole number of from 1 to 8, y is a whole number of from 0 to 7, the sum of x and y being no greater than 8, and z is 8-x-y when A is naphthyl and 6-x-y when A is phenyl; q is a positive number equal to or greater than about 0.5; R is alkyl, halogen, haloalkyl or alkoxy; and R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 , independently, are hydrogen, alkyl, halogen, haloalkyl or alkoxy.
Claim 2
Dependent Claim
149 words
A composition comprising a convertible amino resin selected from the group consisting of amino- or imino-group containing compounds condensed with an aldehyde, dialdehyde and aldehyde precursor and a catalytically effective amount of a thermally-decomposable adduct of an aromatic sulfonic acid, said adduct being of the general formula: ##STR3## wherein A is phenyl or naphthyl and x is a whole number of from 1 to 8, y is a whole number of from 0 to 7, the sum of x and y being no greater than 8, and z is 8-x-y when A is naphthyl and 6-x-y when A is phenyl; q is a positive number equal to or greater than about 0.5; R is alkyl, halogen, haloalkyl or alkoxy; and R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 , independently, are hydrogen, alkyl, halogen, haloalkyl or alkoxy.
Claim 3
Dependent Claim
30 words
A composition as defined in claim 1 wherein the aromatic sulfonic acid component of said adduct is a polyalkylaromatic polysulfonic acid having a molecular weight of at least about 500.
Claim 4
Dependent Claim
28 words
A composition as defined in claim 1 wherein the aromatic sulfonic acid component of the adduct is dinonylnaphthalene disulfonic acid, the nonyl radicals of which are highly branched.
Claim 5
Dependent Claim
17 words
A composition as defined in claim 1 wherein said adduct comprises a compound of the formula: ##STR4##
Claim 6
Dependent Claim
30 words
A composition as defined in claim 1 wherein the aromatic sulfonic acid component of said adduct is a polyalkylaromatic sulfonic acid having a molecular weight of at least about 500.
Claim 7
Dependent Claim
17 words
A composition as defined in claim 5 wherein said polyalkylaromatic sulfonic acid is a dinonylnaphthalene sulfonic acid.
Claim 8
Dependent Claim
20 words
A composition as defined in claim 1 wherein said aromatic sulfonic acid component of said adduct is para-toluene sulfonic acid.
Claim 9
Dependent Claim
29 words
A composition as defined in claim 1 wherein the molar ratio of aromatic sulfonic acid to oxa-azacylopentane compound in said adduct is in the range of from about 1:5-1:2.5.
Claim 10
Dependent Claim
25 words
A composition as defined in claim 1 wherein the molar ratio of aromatic sulfonic acid groups to oxa-azacyclopentane compound in said adduct is about 1:1.1.
Claim 11
Dependent Claim
34 words
A composition as defined in claim 1 wherein the concentration of the aromatic sulfonic acid component of the adduct is from about 0.1 to 12% by weight based on the weight of resin solids.
Claim 12
Dependent Claim
34 words
A composition as defined in claim 10 wherein the concentration of said aromatic sulfonic acid component of the adduct is from about 0.2 to 6% by weight based on the weight of resin solids.
Claim 13
Dependent Claim
15 words
A composition as defined in claim 1 wherein said amino resin is a urea condensate.
Claim 14
Dependent Claim
16 words
A composition as defined in claim 12 wherein said urea condensate is dissolved in a solvent.
Claim 15
Dependent Claim
15 words
A composition as defined in claim 12 wherein said urea condensate is dissolved in water.
Claim 16
Dependent Claim
15 words
A composition as defined in claim 1 wherein said amino resin is a melamine condensate.
Claim 17
Dependent Claim
15 words
A composition as defined in claim 1 wherein said amino resin is a benzoguanamine condensate.
Claim 18
Dependent Claim
15 words
A composition as defined in claim 1 wherein said amino resin is an acetoguanamine condensate.
Claim 19
Dependent Claim
16 words
A composition as defined in claim 15 wherein said melamine condensate is dissolved in a solvent.
Claim 20
Dependent Claim
15 words
A composition as defined in claim 15 wherein said melamine condensate is dissolved in water.
Claim 21
Dependent Claim
16 words
A composition as defined in claim 1 wherein said amino resin is modified with an alcohol.
Claim 22
Dependent Claim
26 words
A composition as defined in claim 1 which also includes a polyfunctional co-reactant capable of combining with said amino resin during conversion into its cured state.
Claim 23
Dependent Claim
39 words
A coating composition, the constituents of which comprise (i) an alkoxylated melamine formaldehyde resin; and (ii) a dinonylnaphthalene disulfonic acid·oxa-azacyclopentane adduct wherein the acid component of the adduct comprises 0.1-6% by weight, based on the weight of resin solids.
Claim 24
Dependent Claim
39 words
A coating composition, the constituents of which comprise (i) an alkoxylated melamine formaldehyde resin; and (ii) a dinonylnaphthalene disulfonic acid·oxa-azacyclopentane adduct wherein the acid component of the adduct comprises 0.1-6% by weight, based on the weight of resin solids.
Claim 25
Dependent Claim
28 words
A composition as defined in claim 22 which also includes a polyfunctional co-reactant capable of combining with said melamine-formaldehyde resin during the conversion thereof to its cured state.
Claim 26
Dependent Claim
21 words
A composition as defined in claim 23 wherein said co-reactant contains hydroxyl groups, carboxyl groups, amide groups or a combination thereof.
Claim 27
Dependent Claim
24 words
A three-dimensional substrate, the surface of which has a coating thereover comprising a reaction product of the components of the composition of claim 1.
Claim 28
Dependent Claim
21 words
A three-dimensional substrate, the surface of which has a coating thereover comprising a reaction product of the components of claim 22.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-04-29 | 1983-10-29 | 1984-04-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-04-29 | 1987-10-29 | 1988-04-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-04-29 | 1991-10-29 | 1992-04-29 | $7700.00 | Window Closed / Lapsed |