US4808638A
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Thiolene compositions on based bicyclic 'ene compounds
Assignee: Henkel Loctite Corp
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Filing: 1987-09-21
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Granted: 1989-02-28
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Expires: 2007-09-21
Abstract
Abstract A curable thiol-ene formulation comprising (a) a polythiol (b) a 'ene compound having a plurality of groups of the formula: ##STR1## where Q is CH 2 , CHCH 3 , C(Ch 3 ) 2 , O, S, NR 1 or SO 2 R 1 is H or alkyl, and m is 0-10, and (c) an effective amount of a free radical initiator.
Inventors
- 👤 Walter J. Steinkraus
- 👤 John Woods
- 👤 John M. Rooney
- 👤 Anthony F. Jacobine
- 👤 David M. Glaser
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 11:38
CPC Classifications
C; C08; C08G; C08G75/00; C08G75/02; C08G75/04; C08G75/045; C08G75/12
Claims Analysis
Total Claims: 25
Claim 1
Independent Claim
85 words
A curable thiol-ene formulation, said formulation being cureable to a crosslinked polymer and comprising: (a) a polythiol, (b) a 'ene compound having a plurality of 'ene groups of the formula, ##STR20## where Q is CR 1 2 , O, S, NR 1 or SO 2 , R 1 is H or alkyl, and m is 0-10, said compound free of allyl, methallyl or 1-propenyl groups, wherein the thiol plus 'ene functionality is greater than four and (c) an effective amount of a free radical initiator.
Claim 2
Dependent Claim
85 words
A curable thiol-ene formulation, said formulation being cureable to a crosslinked polymer and comprising: (a) a polythiol, (b) a 'ene compound having a plurality of 'ene groups of the formula, ##STR20## where Q is CR 1 2 , O, S, NR 1 or SO 2 , R 1 is H or alkyl, and m is 0-10, said compound free of allyl, methallyl or 1-propenyl groups, wherein the thiol plus 'ene functionality is greater than four and (c) an effective amount of a free radical initiator.
Claim 3
Dependent Claim
15 words
A composition as in claim 1 wherein the free radical initiator is a radical photoinitiator.
Claim 4
Dependent Claim
17 words
A composition as in claim 1 wherein the free radical initiator is a peroxide or azonitrile compound.
Claim 5
Dependent Claim
19 words
A composition as in claim 1 wherein the 'ene compound is a compound having a plurality of nadimide groups.
Claim 6
Dependent Claim
43 words
A composition as in claim 1 wherein the 'ene compound has the formula: ##STR21## where n is an integer of 2 or more, R is an n-valent radical, R 5 is H or methyl and X is O, S, or NR 1 .
Claim 7
Dependent Claim
21 words
A composition as in claim 5 where Q is CH 2 or O, X is O and R 5 is H.
Claim 8
Dependent Claim
33 words
A composition as in claim 5 wherein the 'ene compound is: ##STR22## where Q is as defined in claim 1, n' is 1-6 and x and y are integers of 1 or more.
Claim 9
Dependent Claim
12 words
A composition as in claim 4 wherein the 'ene compound is: ##STR23##
Claim 10
Dependent Claim
24 words
A composition as in claim 1 wherein the 'ene compound is a norbornenyl acetal resin having a plurality of groups of the formula: ##STR24##
Claim 11
Dependent Claim
13 words
A composition as in claim 1 wherein the 'ene resin is a polyorganosilane.
Claim 12
Dependent Claim
23 words
A composition as in claim 1 wherein the polythiol is a compound having a plurality of α-mercaptoacetate, α-mercaptopropionate or β-mercaptopropionate ester groups thereon.
Claim 13
Dependent Claim
12 words
A composition as in claim 11 wherein the polythiol is a polyorganosiloxane.
Claim 14
Dependent Claim
18 words
A composition as in claim 1 wherein the polythiol is a compound having a plurality of alkylthiol groups.
Claim 15
Dependent Claim
74 words
A composition as in claim 1 wherein the free radical initiator is a mixture of a peroxide compound and a η 5 , η 6 iron arene complex salt of the formula: ##STR25## where R 6 is an η 6 arene, R 7 is the anion of a cyclopentadienyl compound, L is a di to heptavalent metal or metaloid, Z is a halogen and k is equal to 1 plus the valence of L.
Claim 16
Dependent Claim
73 words
A composition as in claim 14 where LZ k - is selected from the group consisting of SbF 6 - , BF 4 - , AsF 6 - , and PF 6 - ; R 6 is selected from the group consisting of benzene toluene, xylene, methoxybenzene, chlorobenzene, cumene, p-chlorotoluene, naphthalene, methoxynaphthalene, methylnaphthalene, chloronaphthalene, biphenyl, indene, pyrene, or diphenylsulfide; and R 7 is the anion of cyclopentadiene, acetylcyclopentadiene, benzoylcyclopentadiene, butylcyclopentadiene, amylcyclopentadiene or indene.
Claim 17
Dependent Claim
20 words
A method of providing a crosslinked polythioether polymer comprising subjecting a composition as in claim 1 to radical generating conditions.
Claim 18
Independent Claim
135 words
A method of providing a polyimide polymer crosslinked by thioether linkages comprising: providing a formulation comprising a polyimide resin having a plurality of groups of the formula: ##STR26## where Q is CR 2 1 , O, S, NR 1 or SO 2 ; R 1 is H or alkyl and m is 0-10; a polythiol; wherein the thiol plus the 'ene functionality is greater than four and an effective amount of a catalyst comprising a mixture of a peroxide compound and a η 6 , η 5 iron arene complex of the formula: ##STR27## where R 6 is an η 6 arene, R 7 is the anion of a cyclopentadienyl compound, L is a di to heptavalent metal or metaloid, Z is a halogen and k is equal to 1 plus the valence of L.
Claim 19
Independent Claim
135 words
A method of providing a polyimide polymer crosslinked by thioether linkages comprising: providing a formulation comprising a polyimide resin having a plurality of groups of the formula: ##STR26## where Q is CR 2 1 , O, S, NR 1 or SO 2 ; R 1 is H or alkyl and m is 0-10; a polythiol; wherein the thiol plus the 'ene functionality is greater than four and an effective amount of a catalyst comprising a mixture of a peroxide compound and a η 6 , η 5 iron arene complex of the formula: ##STR27## where R 6 is an η 6 arene, R 7 is the anion of a cyclopentadienyl compound, L is a di to heptavalent metal or metaloid, Z is a halogen and k is equal to 1 plus the valence of L.
Claim 20
Dependent Claim
19 words
A method as in claim 17 wherein the polyimide resin is a compound having a plurality of nadimide groups.
Claim 21
Dependent Claim
74 words
A method as in claim 17 wherein LZ k - is selected from the group consisting of SbF 6 - , BF 4 - , AsF 6 - , and PF 6 - ; R 6 is selected from the group consisting of benzene toluene, xylene, mesitylene, methoxybenzene, chlorobenzene, cumene, p-chlorotoluene, naphthalene, methoxynaphthalene, methylnaphthalene, chloronapthalene, biphenyl, indene, pyrene, or diphenylsulfide; and R 7 is the anion of cyclopentadiene, acetylcyclopentadiene, benzoylcyclopentadiene, butylcyclopentadiene, amylcyclopentadiene and indene.
Claim 22
Dependent Claim
33 words
A method as in claim 16 where the radical initiator is a photoinitiator and the radical generating conditions comprise exposing the composition to light of a wave length effective to activate the photoinitiator.
Claim 23
Dependent Claim
15 words
A method as in claim 20 where the photoinitiator is a visible light active photoinitiator.
Claim 24
Dependent Claim
72 words
A method as in claim 20 where the photoinitiator comprises a mixture of a peroxide compound and a η 5 , η 6 -iron arene complex salt of the formula: ##STR28## where R 6 is an η 6 arene, R 7 is the anion of a cyclopentadieneyl compound, L is a di to heptavalent metal or metaloid, Z is a halogen and k is equal to 1 plus the valence of L.
Claim 25
Dependent Claim
13 words
A method as in claim 22 wherein the peroxide compound is a hydroperoxide.
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1992-02-28 | 1992-08-29 | 1993-02-28 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1996-02-28 | 1996-08-29 | 1997-02-28 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2000-02-28 | 2000-08-29 | 2001-02-28 | $7700.00 | Window Closed / Lapsed |