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US3661744A
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Photocurable liquid polyene-polythiol polymer compositions
Assignee: WR Grace and Co
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Filing: 1970-06-08
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Granted: 1972-05-09
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Expires: 1990-06-08
Abstract
Abstract The invention disclosed is for a new photocurable liquid polymer composition which includes a liquid polyene component having a molecule containing at least two unsaturated carbon-to-carbon bonds disposed at terminal positions on a main chain of the molecule, a polythiol component having a molecule containing a multiplicity of pendant or terminally positioned -SH functional groups per average molecule, and a photocuring rate accelerator. The photocurable liquid polymer composition upon curing in the presence of actinic light forms odorless, solid, elastomeric or resinous products which may serve as sealants, coatings, adhesives and molded articles.
Inventors
- 👤 Clifton L Kehr
- 👤 Walter R Wszolek
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 22:37
CPC Classifications
G; G03; G03F; G03F7/00; G03F7/004; G03F7/027; G03F7/0275; B; B65; B65H; B65H7/00; C; C08; C08F; C08F299/00; C08F299/02; C08F299/022; C08F36/00; C08F36/02; C08F36/04; C08G; C08G18/00; C08G18/06; C08G18/28; C08G18/67; C08G18/671; C08G18/6715; C08G18/70; C08G18/81; C08G18/83; C08G18/834; C08G18/835; C08G71/00; C08G75/00; C08G75/02; C08G75/04; C08G75/045; C08G75/12; Y; Y10; Y10S; Y10S521/00; Y10S521/915; Y10T; Y10T428/00; Y10T428/31504; Y10T428/31533
Claims Analysis
Total Claims: 30
Claim 1
Independent Claim
80 words
The composition of claim 1 wherein (A) has the formula: wherein a and b are integers greater than 1; R2 is a member of the group consisting of hydrogen and alkyl; R3 is a member of the group consisting of hydrogen, and saturated alkyl; R4 is a divalent derivative of the group consisting of phenyl, benzyl, alkyl, cycloalkyl, substituted phenyl, substituted benzyl, substituted alkyl and substituted cycloalkyl, said alkyl, cycloalkyl and substituents on members substituted being defined in claim 1.
Claim 2
Dependent Claim
38 words
The composition of claim 5 wherein the photocuring rate accelerator is a member selected from the group consisting of aryl aldehyde, diaryl ketone, alkyl aryl ketone, triaryl phosphine, and a blend of carbon tetrahalide with polynuclear aromatic hydrocarbon.
Claim 3
Dependent Claim
53 words
The composition of claim 1 wherein the polyene has the formula: wherein n is at least 1; and R7 is a member of the group consisting of CH2=CH CH2n , n, hydrogen, phenyl, cycloalkyl and alkyl; said substituent on member which is substituted, the cycloalkyl, and the alkyl defined as in claim 1.
Claim 4
Dependent Claim
11 words
The composition of claim 1 wherein the polyene has the formula:
Claim 5
Dependent Claim
11 words
The composition of claim 1 wherein the polyene has the formula:
Claim 6
Dependent Claim
11 words
The composition of claim 1 wherein the polyene has the formula:
Claim 7
Dependent Claim
11 words
The composition of claim 1 wherein the polyene has the formula:
Claim 8
Dependent Claim
11 words
The composition of claim 1 wherein the polyene has the formula:
Claim 9
Dependent Claim
11 words
The composition of claim 1 wherein the polyene has the formula:
Claim 10
Dependent Claim
11 words
The composition of claim 1 wherein the polyene has the formula:
Claim 11
Dependent Claim
11 words
The composition of claim 1 wherein the polyene has the formula:
Claim 12
Dependent Claim
17 words
The composition of claim 1 wherein the polyene has the formula: where n is at least 1.
Claim 13
Dependent Claim
11 words
The composition of claim 1 wherein the polyene has the formula:
Claim 14
Dependent Claim
56 words
The composition of claim 1 wherein the polyene has the formula: wherein the sum of x + y + z is at least 1; n is at least 1; and R7 is a member of the group consisting of CH2=CH CH2n , hydrogen, alkyl, phenyl, and cycloalkyl said alkyl and cycloalkyl defined as in claim 1.
Claim 15
Dependent Claim
83 words
The composition of claim 1 wherein the polyene has the formula: wherein the sum of x + y + z in each chain segment is at least 1; n is at least 1; R1 is selected from the group consisting of hydrogen, phenyl, benzyl, alkyl, cycloalkyl, and substituted phenyl; and R7 is a member of the group consisting of CH2=CH CH2n , =, hydrogen, alkyl, phenyl, and cycloalkyl; said member which is substituted, the cycloalkyl and the alkyl defined as in claim 1.
Claim 16
Dependent Claim
65 words
The composition of claim 1 wherein the polyene has the formula: wherein the sum of x + y + z in each chain segment is at least 1; n is at least 1; R7 is a member of the group consisting of CH2=CH CH2n , hydrogen, phenyl, cycloalkyl and alkyl; said member which is substituted, the cycloalkyl and the alkyl defined as in claim 1.
Claim 17
Dependent Claim
11 words
The composition of claim 1 wherein the polyene has the formula:
Claim 18
Dependent Claim
20 words
The composition of claim 1 wherein the polyene has the formula: C3H5-O C3H6-O C3H5 wherein y is at least 1.
Claim 19
Dependent Claim
20 words
The composition of claim 1 wherein the mole ratio of ene to thiol is from about 0.2/1 to about 5/1.
Claim 20
Dependent Claim
19 words
The composition of claim 1 wherein the mole ratio of ene to thiol is about 0.75/1 to about 1.5/1.
Claim 21
Dependent Claim
315 words
A process of forming essentially odorless solid polythioether which comprises I. Admixing: A. a terminally unsaturated polyene component which comprises the formula: (A= X)m wherein m is an integer of at least 2; wherein X is where f is an integer from 1 to 9; R is a radical selected from the group consisting of hydrogen, fluorine, chlorine, furyl, thienyl, pyridyl, phenyl and substituted phenyl, benzyl and substituted benzyl, alkyl and substituted alkyl, alkoxy and substituted alkoxy, cycloalkyl and substituted cycloalkyl; said substituents on said substituted members selected from the group consisting of nitro, chloro, fluoro, acetoxy, acetamide, phenyl, benzyl, alkyl, alkoxy and cycloalkyl; said alkyl and alkoxy having from one to nine carbon atoms and said cycloalkyl having from three to eight carbon atoms; wherein (A) is free of reactive carbon-to-carbon unsaturation; free of highly water-sensitive members; and is a polyvalent chamically compatible member of the group consisting of carbonate, carboxylate, carbonyl, ether, silane, silicate, phosphonate, phosphite, phosphate, alkyl and substituted alkyl, cycloalkyl and substitute cycloalkyl, aryl and substituted aryl, urethane and substituted urethane, urea and substituted urea, amine and substituted amine, amide and substituted amide, hydroxyl, heterocyclic carbon containing radical, and mixtures thereof; said substitutents on said members being defined above, said component having a molecular weight in the range from about 64 to 20,000; and a viscosity in the range from essentially 0 to 20 million centipoises at 70* C.; B. a polythiol component having a molecular weight in the range from about 50 to about 20,000 of the general formula: R8=SH)n wherein R8 is a polyvalent organic moiety free from reactive carbon-to-carbon unsaturation and n is at least 2, the sum of m and n being greater than 4, with the ene/thiol mole ratio being selected so as to provide a cross-linked solid, self-supporting cured product; and C. a photocuring rate accelerator, and thereafter II. exposing the mixture to actinic light.
Claim 22
Dependent Claim
26 words
A photocurable composition useful for obtaining an essentially odorless, solid polythioether, said photocurable composition consisting essentially of: A. a terminally unsaturated polyene component having the formula:
Claim 23
Dependent Claim
10 words
The solid product prepared by the process of claim 23.
Claim 24
Dependent Claim
23 words
The process of claim 23 wherein the actinic light is ultraviolet radiation having a wavelength between about 2,000 A and about 4,000 A.
Claim 25
Dependent Claim
21 words
The process of claim 23 wherein the composition contains from 0.0005 to 50 parts by weight of a photocuring rate accelerator.
Claim 26
Dependent Claim
35 words
The process of claim 23 wherein the photocuring rate accelerator is selected from the group consisting of aryl aldehyde; diaryl ketone; alkyl aryl ketone; triaryl phosphine; a blend of carbon tetrahalide with polynuclear aromatic hydrocarbon.
Claim 27
Dependent Claim
14 words
An article comprising the composition of claim 23 as a coating on a substrate.
Claim 28
Dependent Claim
14 words
An article comprising the composition of claim 23 as an adhesive between two substrates.
Claim 29
Dependent Claim
12 words
An article comprising the composition of claim 23 as an elastomeric sealant.
Claim 30
Dependent Claim
11 words
A shaped, molded article cast from the composition of claim 23.
References Cited (Backward Citations)
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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) | 1975-05-09 | 1975-11-08 | 1976-05-09 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1979-05-09 | 1979-11-08 | 1980-05-09 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1983-05-09 | 1983-11-08 | 1984-05-09 | $7700.00 | Window Closed / Lapsed |