US3855040A
Expired / Lapsed
US
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Anaerobic compositions
Assignee: Henkel Loctite Corp
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Filing: 1973-04-02
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Granted: 1974-12-17
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Expires: 1993-04-02
Abstract
Abstract This invention concerns improved curable (polymerizable) anaerobic compositions which contain acrylate ester monomers, peroxy polymerization initiators, a strong acid, and an activator containing a ferrocene moiety, e.g., ferrocene, ferrocene derivatives or polymers incorporating ferrocene. By appropriate selection of the activator, cure speed can be controlled.
Inventors
- 👤 B Malofsky
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 09:15
CPC Classifications
C; C09; C09J; C09J4/00; Y; Y10; Y10T; Y10T428/00; Y10T428/31504; Y10T428/31652; Y10T428/31667; Y10T428/31678; Y10T428/31692; Y10T428/31699
Claims Analysis
Total Claims: 44
Claim 1
Independent Claim
50 words
A POLYMERIZABLE ANAEROBIC COMPOSITION COMPRISING A POLYMERIZABLE ACRYLATE ESTER MONOMER; HYDROPEROXIDE OR A PERESTER POLYMERIZATION INITIATOR CAPABLE OF POLYMERIZING SAID MONOMER IN THE SUBSTANTIAL ABSENCE OF OXYGEN; AND AN EFFECTIVE AMOUNT FOR RAPID POLYMERIZATION OF THE ACRYLATE ESTER MONOMER OF AN ACTIVATOR COMPRISING AN ORGANIC COMPOUND CONTAINING A FERROCENE MOIETY.
Claim 2
Dependent Claim
50 words
A POLYMERIZABLE ANAEROBIC COMPOSITION COMPRISING A POLYMERIZABLE ACRYLATE ESTER MONOMER; HYDROPEROXIDE OR A PERESTER POLYMERIZATION INITIATOR CAPABLE OF POLYMERIZING SAID MONOMER IN THE SUBSTANTIAL ABSENCE OF OXYGEN; AND AN EFFECTIVE AMOUNT FOR RAPID POLYMERIZATION OF THE ACRYLATE ESTER MONOMER OF AN ACTIVATOR COMPRISING AN ORGANIC COMPOUND CONTAINING A FERROCENE MOIETY.
Claim 3
Dependent Claim
33 words
The composition of claim 1 wherein the acrylate ester monomer has a molecular weight of at least about 130 and the polymerization initiator is a hydroperoxide containing up to about 18 carbon atoms.
Claim 4
Dependent Claim
32 words
The composition of claim 1 wherein the activator is selected from the group consisting of ferrocene, polymers incorporating ferrocene, the acyl, aryl, alkyl, hydroxyalkyl and alkenyl derivatives of ferrocene, and mixtures thereof.
Claim 5
Dependent Claim
10 words
The composition of claim 3 wherein the activator is ferrocene.
Claim 6
Dependent Claim
20 words
The composition of claim 3 wherein the activator is a ferrocene polymer incorporating up to about 20 dicyclopentadienyl iron units.
Claim 7
Dependent Claim
15 words
The composition of claim 5 wherein one or both of the cyclopentadienyl groups are substituted.
Claim 8
Dependent Claim
17 words
The composition of claim 3 wherein the activator is an acetyL, benzoyl or benzenesulfonyl derivative of ferrocene.
Claim 9
Dependent Claim
14 words
The composition of claim 3 wherein the activator is an alkyl derivative of ferrocene.
Claim 10
Dependent Claim
14 words
The composition of claim 3 wherein the activator is a hydroxyalkyl derivative of ferrocene.
Claim 11
Dependent Claim
14 words
The composition of claim 3 wherein the activator is an alkenyl derivative of ferrocene.
Claim 12
Dependent Claim
14 words
The composition of claim 3 wherein the activator is an aryl derivative of ferrocene.
Claim 13
Dependent Claim
24 words
The composition of claim 1 wherein the activator is present in an amount between about 0.005 and 1 percent by weight of the composition.
Claim 14
Dependent Claim
11 words
The composition of claim 1 containing in addition a strong acid.
Claim 15
Dependent Claim
17 words
The composition of claim 13 wherein the strong acid has a pKA of less than about 3.
Claim 16
Dependent Claim
17 words
The composition of claim 14 wherein the strong acid has a pKA of less than about 2.
Claim 17
Dependent Claim
62 words
A two-part polymerizable anaerobic composition consisting essentially of: A. A first part comprising a polymerizable acrylate ester monomer; a peroxy polymerization initiator capable of polymerizing said monomer in the substantial absence of oxygen, said polymerization initiator being selected from the group consisting of hydroperoxides and peresters; and B. A second part comprising an activator comprising an organic compound containing a ferrocenyl moiety.
Claim 18
Dependent Claim
62 words
A two-part polymerizable anaerobic composition consisting essentially of: A. A first part comprising a polymerizable acrylate ester monomer; a peroxy polymerization initiator capable of polymerizing said monomer in the substantial absence of oxygen, said polymerization initiator being selected from the group consisting of hydroperoxides and peresters; and B. A second part comprising an activator comprising an organic compound containing a ferrocenyl moiety.
Claim 19
Dependent Claim
18 words
The composition of claim 16 containing in addition an acid having a pKA of less than about 3.
Claim 20
Dependent Claim
13 words
The composition of claim 17 wherein the polymerizable acrylate ester has the formula
Claim 21
Dependent Claim
15 words
The composition of claim 18 wherein q is equal to from 1 to about 4.
Claim 22
Dependent Claim
56 words
The composition of claim 18 wherein the peroxy polymerization initiator comprises from about 0.1 to about 10 percent by weight of the composition and is selected from the group consisting of: A. Hydroperoxides of the formula R4(OOH)z wherein R4 is a hydrocarbon group containing up to about 18 carbon atoms; and B. Peresters of the formula
Claim 23
Dependent Claim
32 words
The composition of claim 17 wherein the activator is selected from the group consisting of ferrocene, polymers incorporating ferrocene, the acyl, aryl, alkyl, hydroxyalkyl and alkenyl derivatives of ferrocene, and mixtures thereof.
Claim 24
Dependent Claim
10 words
The composition of claim 21 wherein the activator is ferrocene.
Claim 25
Dependent Claim
20 words
The composition of claim 21 wherein the activator is a ferrocene polymer incorporating up to about 20 dicyclopentadienyl iron units.
Claim 26
Dependent Claim
15 words
The composition of claim 23 wherein one or both of the cyclopentadienyl groups are substituted.
Claim 27
Dependent Claim
17 words
The composition of claim 21 wherein the activator is an acetyl, benzoyl or benzenesulfonyl derivative of ferrocene.
Claim 28
Dependent Claim
14 words
The composition of claim 21 wherein the activator is an alkyl derivative of ferrocene.
Claim 29
Dependent Claim
14 words
The composition of claim 21 wherein the activator is a hydroxyalkyl derivative of ferrocene.
Claim 30
Dependent Claim
14 words
The composition of claim 21 wherein the activator is an alkenyl derivative of ferrocene.
Claim 31
Dependent Claim
14 words
The composition of claim 21 wherein the activator is an aryl derivative of ferrocene.
Claim 32
Dependent Claim
48 words
The composition of claim 21 wherein the second part is dossolved in a volatile solvent, the activator comprises between about 0.05 and about 10 percent by weight of the second part, and the acid comprises between about 0.1 and about 5 percent by weight of the second part.
Claim 33
Dependent Claim
92 words
A two-paRt polymerizable composition consisting essentially of: A. A first part comprising a polymerizable acrylate ester monomer; from about 0.005 to about 1 percent by weight of an activator comprising an organic compound containing a ferrocenyl moiety; and from about 0.1 to about 10 percent by weight of a peroxy polymerization initiator capable of polymerizing said monomer in the substantial absence of oxygen, said polymerization initiator being selected from the group consisting of hydroperoxides and peresters; and B. A second part comprising an acid having a pKA of less than about 3.
Claim 34
Dependent Claim
92 words
A two-paRt polymerizable composition consisting essentially of: A. A first part comprising a polymerizable acrylate ester monomer; from about 0.005 to about 1 percent by weight of an activator comprising an organic compound containing a ferrocenyl moiety; and from about 0.1 to about 10 percent by weight of a peroxy polymerization initiator capable of polymerizing said monomer in the substantial absence of oxygen, said polymerization initiator being selected from the group consisting of hydroperoxides and peresters; and B. A second part comprising an acid having a pKA of less than about 3.
Claim 35
Dependent Claim
32 words
The composition of claim 31 wherein the activator is selected from the group consisting of ferrocene, polymers incorporating ferrocene, the acyl, aryl, alkyl, hydroxyalkyl and alkenyl derivatives of ferrocene, and mixtures thereof.
Claim 36
Dependent Claim
93 words
A two-part polymerizable anaerobic composition consisting essentially of: A. A first part comprising a polymerizable acrylate ester monomer; from about 0.01 to about 5 percent by weight of an acid having a pKA of less than about 3, and from about 0.1 to about 10 percent by weight of a peroxy polymerization initiator capable of polymerizing said monomer in the substantial absence of oxygen, said polymerization initiator being selected from the group consisting of hydroperoxides and peresters; and B. A second part comprising an activator comprising an organic compound containing a ferrocenyl moiety.
Claim 37
Dependent Claim
93 words
A two-part polymerizable anaerobic composition consisting essentially of: A. A first part comprising a polymerizable acrylate ester monomer; from about 0.01 to about 5 percent by weight of an acid having a pKA of less than about 3, and from about 0.1 to about 10 percent by weight of a peroxy polymerization initiator capable of polymerizing said monomer in the substantial absence of oxygen, said polymerization initiator being selected from the group consisting of hydroperoxides and peresters; and B. A second part comprising an activator comprising an organic compound containing a ferrocenyl moiety.
Claim 38
Dependent Claim
32 words
The composition of claim 33 wherein the activator is selected from the group consisting of ferrocene, polymers incorporating ferrocene, the acyl, aryl alkyl, hydroxyalkyl and alkenyl derivatives of ferrocene, and mixtures thereof.
Claim 39
Dependent Claim
14 words
The composition of claim 34 wherein the activator is dissolved in a volatile solvent.
Claim 40
Dependent Claim
116 words
A process for sealing or bonding substrates which comprises: A. Applying to at least one of said substrates a primer composition comprising a mixture of an acid having a pKA less than about 3 and an activator comprising an organic compound containing a ferrocenyl moiety; and B. Applying to at least one of said substrates a polymerizable composition comprising a polymerizable acrylate ester monomer and a peroxy polymerization initiator capable of polymerizing said monomer in the substantial absence of oxygen, said polymerization initiator being selected from the group consisting of hydroperoxides and peresters; C. And thereafter placing said substrates in an abutting relationship until the polymerizable composition has hardened sufficiently to seal or bond said substrates.
Claim 41
Dependent Claim
116 words
A process for sealing or bonding substrates which comprises: A. Applying to at least one of said substrates a primer composition comprising a mixture of an acid having a pKA less than about 3 and an activator comprising an organic compound containing a ferrocenyl moiety; and B. Applying to at least one of said substrates a polymerizable composition comprising a polymerizable acrylate ester monomer and a peroxy polymerization initiator capable of polymerizing said monomer in the substantial absence of oxygen, said polymerization initiator being selected from the group consisting of hydroperoxides and peresters; C. And thereafter placing said substrates in an abutting relationship until the polymerizable composition has hardened sufficiently to seal or bond said substrates.
Claim 42
Dependent Claim
32 words
The process of claim 36 wherein the activator is selected from the group consisting of ferrocene, polymers incorporating ferrocene, the acyl, aryl, alkyl, hydroxyalkyl and alkenyl derivatives of ferrocene, and mixtures thereof.
Claim 43
Dependent Claim
21 words
The process of claim 36 wherein the activator is contained in said polymerizable composition, and is deleted from said primer composition.
Claim 44
Dependent Claim
21 words
The process of claim 36 wherein the acid is contained in said polymerizable composition, and is deleted from said primer 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) | 1977-12-16 | 1978-06-17 | 1978-12-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1981-12-16 | 1982-06-17 | 1982-12-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1985-12-16 | 1986-06-17 | 1986-12-17 | $7700.00 | Window Closed / Lapsed |