US3650802A
Expired / Lapsed
US
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Process for coating a substrate with a polyene/polythiol composition
Assignee: WR Grace and Co
•
Filing: 1969-03-07
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Granted: 1972-03-21
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Expires: 1989-03-07
Abstract
Abstract This invention relates to curing of coatings, sealants and laminates under ambient conditions without affecting the pot life of a curable liquid composition comprising a polyene containing at least two reactive unsaturated carbon to carbon bonds per molecule and a polythiol containing at least two thiol groups per molecule, the total combined functionality of (a) the reactive unsaturated carbon to carbon bonds per molecule in the polyene and (b) the thiol groups per molecule in the polythiol being greater than four which comprises having present at least a minor amount of an iron-containing material either as a portion of the substrate, as a primer coat for the substrate or as a top coat for the curable composition. In the case where oxygen is excluded from the reaction, a minor amount of an oxime ester is added to the system to assure curing to a solidified product.
Inventors
- 👤 Clifton Leroy Kehr
- 👤 James Leverette Guthrie
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 18:34
CPC Classifications
B; B05; B05D; B05D3/00; B05D3/10; B05D3/102; B05D1/00; B05D1/36; B05D3/104; B05D3/107; B05D3/108; C; C08; C08G; C08G18/00; C08G18/06; C08G18/08; C08G18/16; C08G18/22; C08G18/222; C08G18/28; C08G18/67; C08G18/671; C08G18/6715; C08G18/70; C08G18/81; C08G18/8108; C08G18/83; C08G18/834; C08G18/835; C08G75/00; C08G75/02; C08G75/04; C08G75/045; C08G75/12; C08L; C08L81/00; B05D2202/00; B05D2202/20; B05D2202/25; B05D2203/00; B05D2203/30; B05D2203/35
Claims Analysis
Total Claims: 44
Claim 1
Independent Claim
46 words
The process according to claim 1 wherein the polyene is the reaction product of polytetramethylene ether glycol having a molecular weight of about 1000, polytetramethylene ether glycol having a molecular weight of about 2000, tolylene diisocyanate and allyl isocyanate in a mole ratio of 1:1:1:2 respectively.
Claim 2
Dependent Claim
60 words
applying as a top coat to said curable liquid composition an iron-containing material selected from the group consisting of iron, iron oxides, iron salts, and iron chelates, the amount of iron in the iron-containing material being in the range 0.0001 to 0.01 percent by weight of the polyene/polythiol composition, said iron-containing material being the catalyst for curing said composition, and
Claim 3
Dependent Claim
93 words
applying to said prime coat a liquid curable composition comprising a polyene containing at least two reactive unsaturated carbon to carbon bonds per molecule, a polythiol containing at least two thiol groups per molecule, the total combined functionality of (a) the reactive unsaturated carbon to carbon bonds per molecule in the polyene and (b) the thiol groups per molecule in the polythiol being greater than four, and the weight ratio of the polyene to the polythiol being 2-98:98-2, respectively, and 0.1-5 percent by weight of the polyene/polythiol composition of an oxime ester, and
Claim 4
Dependent Claim
9 words
allowing the curable composition to harden under ambient conditions.
Claim 5
Dependent Claim
9 words
allowing the curable composition to harden under ambient conditions.
Claim 6
Dependent Claim
13 words
The process according to claim 1 wherein the polyene is a styrene/butadiene rubber.
Claim 7
Dependent Claim
34 words
The process according to claim 1 wherein the polyene is the reaction product of polytetramethylene ether glycol having a molecular weight of about 2000 and allyl isocyanate in a mole ratio of 1:2 respectively.
Claim 8
Dependent Claim
28 words
The process according to claim 1 wherein the polyene is the reaction product of a solid polyester diol and allyl isocyanate in a mole ratio of 1:2 respectively.
Claim 9
Dependent Claim
35 words
The process according to claim 1 wherein the polyene is the reaction product of polyoxypropylene diol having a molecular weight of about 2000, tolylene 2,4-diisocyanate and allyl alcohol in a mole ratio of 1:2:2 respectively.
Claim 10
Dependent Claim
34 words
The process according to claim 1 wherein the polyene is the reaction product of a phthalate or succinate esterol derived from polytetramethylene ether glycol and allyl isocyanate having a molecular weight of about 4000.
Claim 11
Dependent Claim
34 words
The process according to claim 1 wherein the polyene is the reaction product of polytetramethylene ether glycol having a molecular weight of about 3000 and allyl isocyanate in a mole ratio of 1:2 respectively.
Claim 12
Dependent Claim
35 words
The process according to claim 1 wherein the polyene is the reaction product of polyoxypropylene triol having a molecular weight of about 1000 to 6000 and allyl isocyanate in a mole ratio of 1:3 respectively.
Claim 13
Dependent Claim
11 words
The process according to claim 1 wherein the polyene is poly-1,3-butadiene.
Claim 14
Dependent Claim
26 words
The process according to claim 1 wherein the polyene is the triacrylate of the reaction product of trimethylol propane and about 3-30 moles of ethylene oxide.
Claim 15
Dependent Claim
12 words
The process according to claim 1 wherein the polyene is triallyl urea.
Claim 16
Dependent Claim
13 words
The process according to claim 1 wherein the polyene is cellulose acetate methacrylate.
Claim 17
Dependent Claim
25 words
The process according to claim 1 wherein the polyene is the reaction product of 1,4-butanediol and allyl isocyanate in a mole ratio of 1:2 respectively.
Claim 18
Dependent Claim
110 words
The process according to claim 1 wherein the polyene is formed by reacting either a. an organic epoxide containing at least two groups in its structure with a member of the group consisting of hydrazine, primary amines, secondary amines, tertiary amines, amine salts, organic alcohols and organic acids wherein said group member contain at least one organic substituent containing a reactive ethylenically or ethynylically unsaturated group, or b. an organic epoxide containing at least one organic substituent containing a reactive ethylenically or ethynylically unsaturated group with a member of the group consisting of hydrazine and an organic material containing at leAst two active hydrogen functions from the group consisting of
Claim 19
Dependent Claim
28 words
The process according to claim 15 wherein the polyene is the reaction product of 1 mole of diglycidyl ether of Bisphenol A and 2 moles of allyl amine.
Claim 20
Dependent Claim
28 words
The process according to claim 15 wherein the polyene is the reaction product of 1 mole of diglycidyl ether of Bisphenol A and 2 moles of allyl hydrazine.
Claim 21
Dependent Claim
28 words
The process according to claim 15 wherein the polyene is the reaction product of 1 mole of diglycidyl ether of Bisphenol A and 2 moles of diallyl amine.
Claim 22
Dependent Claim
25 words
The process according to claim 15 wherein the polyene is the reaction product of 1 mole of polyoxypropylenetriamine and 3 moles of allyl glycidyl ether.
Claim 23
Dependent Claim
33 words
The process according to claim 1 wherein the oxime ester is a member of the group consisting of dimethylglyoxime dibenzoate, glyoxime dibenzoate, 3-phenyl-4,5-dihydro-6-oxo-1,2-oxazine, cyclohexanone oxime benzoate, cycloheptanone oxime benzoate, and 2-methylcyclohexanone oxime benzoate.
Claim 24
Dependent Claim
8 words
A process for coating a substrate which comprises
Claim 25
Dependent Claim
46 words
The process according to claim 21 wherein the polyene is the reaction product of polytetramethylene ether glycol having a molecular weight of about 1000, polytetramethylene ether glycol having a molecular weight of about 2000, tolylene diisocyanate and allyl isocyanate in a mole ratio of 1:1:1:2 respectively.
Claim 26
Dependent Claim
13 words
The process according to claim 21 wherein the polyene is a styrene/butadiene rubber.
Claim 27
Dependent Claim
34 words
The process according to claim 21 wherein the polyene is the reaction product of polytetramethylene ether glycol having a molecular weight of about 2000 and allyl isocyanate in a mole ratio of 1:2 respectively.
Claim 28
Dependent Claim
28 words
The process according to claim 21 wherein the polyene is the reaction product of a solid polyester diol and allyl isocyanate in the mole ratio of 1:2 respectively.
Claim 29
Dependent Claim
35 words
The process according to claim 21 wherein the polyene is the reaction product of polyoxypropylene diol having a molecular weight of about 2000, tolylene 2,4-diisocyanate and allyl alcohol in a mole ratio of 1:2:2 respectively.
Claim 30
Dependent Claim
34 words
The process according to claim 21 wherein the polyene is the reaction product of a phthalate or succinate esterol derived from polytetramethylene ether glycol and allyl isocyanate having a molecular weight of about 4000.
Claim 31
Dependent Claim
34 words
The process according to claim 21 wherein the polyene is the reaction product of polytetramethylene ether glycol having a molecular weight of about 3000 and allyl isocyanate in a mole ratio of 1:2 respectively.
Claim 32
Dependent Claim
32 words
The process according to claim 21 wherein the polyene is the reaction product of polyoxypropylene triol having a molecular weight of 1000-6000 and allyl isocyanate in a mole ratio of 1:3 respectively.
Claim 33
Dependent Claim
12 words
The process according to claim 21 wherein the polyene is a poly-1,3-butadiene.
Claim 34
Dependent Claim
26 words
The process according to claim 21 wherein the polyene is the triacrylate of the reaction product of trimethylol propane and about 3-30 moles of ethylene oxide.
Claim 35
Dependent Claim
12 words
The process according to claim 21 wherein the polyene is triallyl urea.
Claim 36
Dependent Claim
13 words
The process according to claim 21 wherein the polyene is cellulose acetate methacrylate.
Claim 37
Dependent Claim
25 words
The process according to claim 21 wherein the polyene is the reaction product of 1,4-butanediol and allyl isocyanate in a mole ratio of 1:2 respectively.
Claim 38
Dependent Claim
110 words
The process according to claim 21 wherein the polyene is formed by reacting either a. an organic epoxide containing at least two groups in its structure with a member of the group consisting of hydrazine, primary amines, secondary amines, tertiary amines amine salts, organic alcohols and organic acids wherein said group members contain at least one organic substituent containing a reactive ethylenically or ethynylically unsaturated group, or b. an organic epoxide containing at least one organic substituent containing a reactive ethylenically or ethynylically unsaturated group with a member of the group consisting of hydrazine and an organic material containing at least two active hydrogen functions from the group consisting of
Claim 39
Dependent Claim
28 words
The process according to claim 21 wherein the polyene is the reaction product of 1 mole of diglycidly ether of Bisphenol A and 2 moles of allyl hydrazine.
Claim 40
Dependent Claim
28 words
The process according to claim 21 wherein the polyene is the reaction product of 1 mole of diglycidyl ether of Bisphenol A and 2 moles of allyl amine.
Claim 41
Dependent Claim
28 words
The process according to claim 21 wherein the polyene is the reaction product of 1 mole of diglycidyl ether of Bisphenol A and 2 moles of diallyl amine.
Claim 42
Dependent Claim
25 words
The process according to claim 21 wherein the polyene is the reaction product of 1 mole of polyoxypropylenetriamine and 3 moles of allyl glycidyl ether.
Claim 43
Dependent Claim
33 words
The process according to claim 21 wherein the oxime ester is a member of the group consisting of dimethylglyoxime dibenzoate, glyoxime dibenzoate, 3-phenyl-4,5-dihydro-6oxo-1,2-oxazine, cyclohexanone oxime benzoate, cycloheptanone oxime benzoate, and 2-methylcyclohexanone oxime benzoate.
Claim 44
Dependent Claim
112 words
A process for coating an iron substrate which comprises (1) applying to said substrate a liquid curable composition comprising a polyene containing at least two reactive unsaturated carbon to carbon bonds per molecule and a polythiol containing at least two thiol groups per molecule, the total combined functionality of (a) the reactive unsaturated carbon to carbon bonds per molecule in the polyene and (b) the thiol groups per molecule in the polythiol being greater than four and the weight ratio of the polyene to the polythiol being 2-98:98-2, respectively, and (2) allowing the curable composition to harden under ambient conditions, said iron in said substrate being a catalyst for curing said composition.
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) | 1975-03-21 | 1975-09-20 | 1976-03-21 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1979-03-21 | 1979-09-20 | 1980-03-21 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1983-03-21 | 1983-09-20 | 1984-03-21 | $7700.00 | Window Closed / Lapsed |