US4017650A
Expired / Lapsed
US
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Method of coating using active radiation curable polyene-polythiol compositions
Assignee: WR Grace and Co
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Filing: 1976-05-21
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Granted: 1977-04-12
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Expires: 1996-05-21
Abstract
Abstract A curable composition comprising compatible polyene and polythiol in which both the components are derived from a hydantoin glycol. The polyene is typically a reaction product of N,N'-bis(2-hydroxyethyl) dimethylhydantoin, a diisocyanate and an unsaturated alcohol, e.g., allyl alcohol. The polythiol is typically a reaction product of N,N'-bis(2-hydroxyethyl) dimethylhydantoin and a mercapto carboxylic acid, e.g., beta -mercaptopropionic acid. Upon exposure to a free radical generator, e.g., actinic radiation, this polyene-polythiol composition cures to solid, insoluble, chemically resistant, cross-linked polythioether products.
Inventors
- 👤 Charles R. Morgan
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 06:56
CPC Classifications
C; C08; C08J; C08J3/00; C08J3/28; C08G; C08G18/00; C08G18/06; C08G18/28; C08G18/30; C08G18/38; C08G18/3819; C08G18/3842; C08G18/3848; C08G18/67; C08G18/671; C08G18/6715; C08G18/83; C08G18/834; C08G18/835; C08G65/00; C08G65/02; C08G65/26; C08G65/2618; C08G65/2621; C08G65/263; C08G75/00; C08G75/02; C08G75/04; C08G75/045; C08G75/12; C08J2381/00; C08J2381/02
Claims Analysis
Total Claims: 8
Claim 1
Independent Claim
240 words
A process which comprises: A. applying to the surface of a substrate a layer of a composition consisting essentially of: 1 A polyene of the formula: ##STR23## wherein A and B are polyvalent organic radical members free of reactive carbon to carbon unsaturation and are independtly selected from the group consisting of aryl, substituted aryl, aralkyl, substituted aralkyl, cycloalkyl, substituted cycloaklyl, alkyl and substituted alkyl containing 1 to 36 carbon atoms and mixtures thereof, said group members can be connected by a chemically compatible linkage selected from the group consisting of --0--, --S--, carboxylate, carbonate, carbonyl, urethane and substituted urethane, urea and substituted urea, amide and substituted amide, amine and substituted amine and hydrocarbon; Z is a divalent chemically compatible linkage selected from the group consisting of ##STR24## --O-- and --S--; X is a member selected from the group consisting of (a) --(CH 2 ) d --CR'=CHR, (b) --O--(CH 2 ) d --CR'=CHR, (c) --S--(CH 2 ) --CR'CR'=CHR , (d) --(CH 2 ) d --C.tbd.CR, (e) --0--(CH 2 ) d --C.tbd.CR, (f) --S--(CH 2 ) d --C.tbd.CR; and mixtures thereof; where R and R' each are independently selected radical; the group consisting of hydrogen and methyl radicals d, p and q are each integers from 0 0 to 1; m and n are each integers of at least 1; with m + n from 2 to 22 and r at least 1, and y from 1 to 10; and 2.
Claim 2
Dependent Claim
240 words
A process which comprises: A. applying to the surface of a substrate a layer of a composition consisting essentially of: 1 A polyene of the formula: ##STR23## wherein A and B are polyvalent organic radical members free of reactive carbon to carbon unsaturation and are independtly selected from the group consisting of aryl, substituted aryl, aralkyl, substituted aralkyl, cycloalkyl, substituted cycloaklyl, alkyl and substituted alkyl containing 1 to 36 carbon atoms and mixtures thereof, said group members can be connected by a chemically compatible linkage selected from the group consisting of --0--, --S--, carboxylate, carbonate, carbonyl, urethane and substituted urethane, urea and substituted urea, amide and substituted amide, amine and substituted amine and hydrocarbon; Z is a divalent chemically compatible linkage selected from the group consisting of ##STR24## --O-- and --S--; X is a member selected from the group consisting of (a) --(CH 2 ) d --CR'=CHR, (b) --O--(CH 2 ) d --CR'=CHR, (c) --S--(CH 2 ) --CR'CR'=CHR , (d) --(CH 2 ) d --C.tbd.CR, (e) --0--(CH 2 ) d --C.tbd.CR, (f) --S--(CH 2 ) d --C.tbd.CR; and mixtures thereof; where R and R' each are independently selected radical; the group consisting of hydrogen and methyl radicals d, p and q are each integers from 0 0 to 1; m and n are each integers of at least 1; with m + n from 2 to 22 and r at least 1, and y from 1 to 10; and 2.
Claim 3
Dependent Claim
101 words
A polythiol of the formula: ##STR25## wherein m and n are each at least 1 and m + n is 2 to 22 and R 3 is a polyvalent organic radical member free of reactive carbon-to-carbon unsaturation and is selected from the group consisting of aryl; substituted aryl, aralkyl, substituted aralkyl, cylcoalkyl, substituted cycloalkyl, alkyl and substituted alkyl groups containing 1 to 16 carbon atoms and mixtures thereof, the total combined functionality of (a) the reactive carbon to carbon bonds per molecule in the polyene and (b) the thiol groups per molecule in the polythiol being greater than 4 and 3.
Claim 4
Dependent Claim
101 words
A polythiol of the formula: ##STR25## wherein m and n are each at least 1 and m + n is 2 to 22 and R 3 is a polyvalent organic radical member free of reactive carbon-to-carbon unsaturation and is selected from the group consisting of aryl; substituted aryl, aralkyl, substituted aralkyl, cylcoalkyl, substituted cycloalkyl, alkyl and substituted alkyl groups containing 1 to 16 carbon atoms and mixtures thereof, the total combined functionality of (a) the reactive carbon to carbon bonds per molecule in the polyene and (b) the thiol groups per molecule in the polythiol being greater than 4 and 3.
Claim 5
Dependent Claim
10 words
a photocuring rate accelerator and, thereafter, exposing the layer to
Claim 6
Dependent Claim
10 words
a photocuring rate accelerator and, thereafter, exposing the layer to
Claim 7
Dependent Claim
20 words
actinic radiation thereby curing said composition. 2. The process according to claim 1 wherein the actinic radiation is actinic laser
Claim 8
Dependent Claim
24 words
radiation. 3. The process according to claim 1 wherein the actinic radiation is ultraviolet light having a wavelenght wavelength about 2000A and about 4000A.
References Cited (Backward Citations)
US3839354A
Cited
US3697395A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-04-11 | 1980-10-11 | 1981-04-12 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-04-11 | 1984-10-11 | 1985-04-12 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-04-11 | 1988-10-11 | 1989-04-12 | $7700.00 | Window Closed / Lapsed |