US4533446A
Expired / Lapsed
US
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Radiation-activatable anaerobic adhesive composition
Assignee: Henkel Loctite Ireland Ltd
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Filing: 1983-07-20
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Granted: 1985-08-06
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Expires: 2003-07-20
Abstract
Abstract An anaerobic adhesive composition activatable by ultraviolet or visible radiation is disclosed which forms strong bonds with lapped surfaces and which is comprised of (a) an anaerobically polymerizable acrylate ester monomer, (b) a compound which decomposes upon exposure to ultraviolet or visible light radiation to release a strong acid, (c) a peroxy free radical initiator capable of initiating the polymerization of the monomer upon substantial exclusion of oxygen and (d) an activator of anaerobic polymerization which, in the presence of a strong acid, reacts with the peroxide initiator to produce free radicals to catalyze the anaerobic polymerization of the monomer.
Inventors
- 👤 Paul Conway
- 👤 David P. Melody
- 👤 John Woods
- 👤 J. Eisirt Casey
- 👤 Bernard J. Bolger
- 👤 Francis R. Martin
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 01:59
CPC Classifications
C; C09; C09J; C09J4/00; C08; C08F; C08F290/00; C08F290/02; C08F290/06
Claims Analysis
Total Claims: 24
Claim 1
Independent Claim
193 words
A radiation activatable anaerobic adhesive composition comprised of (a) an anaerobically curable acrylate ester monomer, (b) a compound which decomposes upon exposure to ultraviolet or visible light radiation to release a strong acid, said compound having the formula [A] d + [MX e ] - (e-f) where A is a cation selected from the group consisting of iodonium and sulfonium cations, M is a metal or metalloid, X is a halogen radical, d=e-f, f=the valence of M and is an integer equal to 2 to 7, inclusive, e is greater than f and is an integer having a value up to 8, (c) a peroxy free radical initiator capable of initiating the polymerization of the monomer in the substantial absence of oxygen, and (d) an activator of anaerobic polymerization which in the presence of a strong acid reacts with the peroxide initiator to produce free radicals to catalyze the anaerobic polymerization of the monomer, said activator selected from ferrocenyl compounds having the formula R 1 C 5 H 4 --FeC 5 H 4 R 2 where R 1 and R 2 are selected from --H, --COOH, --CO.CH 3 , CO.φ, n-alkyl and vinyl.
Claim 2
Dependent Claim
193 words
A radiation activatable anaerobic adhesive composition comprised of (a) an anaerobically curable acrylate ester monomer, (b) a compound which decomposes upon exposure to ultraviolet or visible light radiation to release a strong acid, said compound having the formula [A] d + [MX e ] - (e-f) where A is a cation selected from the group consisting of iodonium and sulfonium cations, M is a metal or metalloid, X is a halogen radical, d=e-f, f=the valence of M and is an integer equal to 2 to 7, inclusive, e is greater than f and is an integer having a value up to 8, (c) a peroxy free radical initiator capable of initiating the polymerization of the monomer in the substantial absence of oxygen, and (d) an activator of anaerobic polymerization which in the presence of a strong acid reacts with the peroxide initiator to produce free radicals to catalyze the anaerobic polymerization of the monomer, said activator selected from ferrocenyl compounds having the formula R 1 C 5 H 4 --FeC 5 H 4 R 2 where R 1 and R 2 are selected from --H, --COOH, --CO.CH 3 , CO.φ, n-alkyl and vinyl.
Claim 3
Dependent Claim
37 words
The composition of claim 1 wherein the anaerobically polymerizable acrylate ester monomer is a block copolymer prepared by reacting a hydroxyalkyl methacrylate with the reaction product of a polyisocyanate and a polyalkylene glycol having unreacted isocyanate functionality.
Claim 4
Dependent Claim
39 words
The composition of claim 1 wherein the anaerobically curable acrylate ester monomer is a block copolymer prepared by reacting hydroxypropyl methacrylate with the reaction product of toluene diisocyanate and the hydroxypolyoxy-propylene derivative of trimethylol propane having unreacted isocyanate functionality.
Claim 5
Dependent Claim
37 words
The composition of claim 1 wherein the anaerobically polymerizable acrylate ester monomer is a urethane-acrylate prepared by the reaction of a polyisocyanate and a monofunctionally substituted acrylate ester having an active hydrogen atom on the functional substituent.
Claim 6
Dependent Claim
31 words
The composition of claim 1 wherein the anaerobically polymerizable acrylate ester monomer is a urethane-acrylate prepared by reacting hydroxyethyl methacrylate with the reaction product of toluene diisocyanate and hydrogenated Bisphenol A.
Claim 7
Dependent Claim
10 words
The composition of claim 1 wherein the cation is sulfonium.
Claim 8
Dependent Claim
10 words
The composition of claim 1 wherein the cation is iodonium.
Claim 9
Dependent Claim
13 words
The composition of claim 1 wherein MX e is PF 6 - .
Claim 10
Dependent Claim
13 words
The composition of claim 1 wherein MX e is AsF 6 - .
Claim 11
Dependent Claim
13 words
The composition of claim 1 wherein MX e is SbF 6 - .
Claim 12
Dependent Claim
13 words
The composition of claim 1 wherein the radiation decomposible compound is diphenyliodonium hexafluorophosphate.
Claim 13
Dependent Claim
13 words
The composition of claim 1 wherein the radiation decomposible compound is ditolyliodonium hexafluorophosphate.
Claim 14
Dependent Claim
13 words
The composition of claim 1 wherein the radiation decomposible compound is diphenyliodonium hexafluoroarsenate.
Claim 15
Dependent Claim
12 words
The composition of claim 1 wherein the radiation decomposible compound is ##STR9##
Claim 16
Dependent Claim
15 words
The composition of claim 1 wherein the peroxy free radical initiator is an organic hydroperoxide.
Claim 17
Dependent Claim
12 words
The composition of claim 15 wherein the organic hydroperoxide is cumene hydroperoxide.
Claim 18
Dependent Claim
11 words
The composition of claim 1 wherein the ferrocenyl compound is ferrocene.
Claim 19
Dependent Claim
19 words
The composition of claim 1 wherein the ferrocenyl compound is (φ.CO.C 5 H 4 )Fe(C 5 H 5 ).
Claim 20
Dependent Claim
23 words
The composition of claim 1 wherein the ferrocenyl compound is (CH 3 .C 5 H 4 )Fe(CH 3 .C 5 H 4 ).
Claim 21
Dependent Claim
32 words
The composition of claim 1 wherein the radiation decomposible compound is present in the adhesive composition at a concentration of about 0.1 to about 5 percent by weight of the total composition.
Claim 22
Dependent Claim
33 words
The composition of claim 1 wherein the peroxy free radical initiator is present in the adhesive composition at a concentration of about 1.0 to about 3.0 percent by weight of the total composition.
Claim 23
Dependent Claim
30 words
The composition of claim 1 wherein the activator is present in the adhesive composition at a concentration of about 0.25 to about 5.0 percent by weight of the total composition.
Claim 24
Dependent Claim
90 words
A process for adhering substrates which comprises applying the composition of claim 1 to the surface of one or both of the substrates to be bonded to prepare a coated surface, exposing at least one of the coated surfaces to a source of ultraviolet or visible radiation of an intensity sufficient to activate the composition, placing the irradiated coated surface in abutting relationship with the other coated or uncoated surface to substantially exclude air and then allowing the composition to cure and harden to adhere the surfaces to each other.
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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) | 1988-08-05 | 1989-02-04 | 1989-08-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-08-05 | 1993-02-04 | 1993-08-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-08-05 | 1997-02-04 | 1997-08-06 | $7700.00 | Window Closed / Lapsed |