US4490515A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Hot strength cyanoacrylate adhesive composition
Assignee: Henkel Loctite Corp
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Filing: 1983-03-07
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Granted: 1984-12-25
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Expires: 2003-03-07
Abstract
Abstract An adhesive composition having improved thermal properties, especially hot strength, comprising (a) at least one polymerizable cyanoacrylate monomer, (b) about 0.1 to about 10% by weight of at least one polymerizable acrylate ester and (c) about 0.1 to about 20% by weight of an additive selected from the group consisting of the following compounds: ##STR1## wherein R 7 and R 8 are selected from the group consisting of alkyl, cycloalkyl, aralky and alkaryl. The compositions disclosed herein have excellent hot strength properties for long periods at 250° F. or more.
Inventors
- 👤 Chris S. Mariotti
- 👤 Ju-Chao Liu
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 05:02
CPC Classifications
C; C09; C09J; C09J4/00
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
207 words
A room temperature curing adhesive composition having improved thermal properties comprising: (a) at least one polymerizable cyanoacrylate monomer of the general formula ##STR8## wherein R is C 1-16 alkyl, cycloalkyl, alkenyl, cycloalkenyl, phenyl or heterocyclic radical; (b) about 0.1 to about 20% by weight of the total composition of at least one polymerizable acrylate ester monomer of the general formula: ##STR9## wherein R 1 is H, CH 3 or lower alkyl and R 2 is alkenyl, or ##STR10## wherein R 3 is H, C 1-4 alkyl or hydroxyalkyl or R 5 OCH 2 --; R 4 is H, OH or R 5 O--; R 5 is CH 2 ═CR 6 C═O; R 6 is H, halogen of C 1-4 alkyl; m is an integer from 1 to 8, k is an integer from 1 to 20; and p is 0 or 1; (c) about 0.1 to about 20% by weight of the total composition of an additive selected from the group consisting of ##STR11## wherein R 7 and R 8 are selected from the group consisting of alkyl, cycloalkyl, aryalkyl, alkaryl, aryl, aryloxy and alkoxy; and (d) an anionic polymerization inhibitor present in the amounts of about 0.1% to about 10% by weight of the total composition.
Claim 2
Dependent Claim
207 words
A room temperature curing adhesive composition having improved thermal properties comprising: (a) at least one polymerizable cyanoacrylate monomer of the general formula ##STR8## wherein R is C 1-16 alkyl, cycloalkyl, alkenyl, cycloalkenyl, phenyl or heterocyclic radical; (b) about 0.1 to about 20% by weight of the total composition of at least one polymerizable acrylate ester monomer of the general formula: ##STR9## wherein R 1 is H, CH 3 or lower alkyl and R 2 is alkenyl, or ##STR10## wherein R 3 is H, C 1-4 alkyl or hydroxyalkyl or R 5 OCH 2 --; R 4 is H, OH or R 5 O--; R 5 is CH 2 ═CR 6 C═O; R 6 is H, halogen of C 1-4 alkyl; m is an integer from 1 to 8, k is an integer from 1 to 20; and p is 0 or 1; (c) about 0.1 to about 20% by weight of the total composition of an additive selected from the group consisting of ##STR11## wherein R 7 and R 8 are selected from the group consisting of alkyl, cycloalkyl, aryalkyl, alkaryl, aryl, aryloxy and alkoxy; and (d) an anionic polymerization inhibitor present in the amounts of about 0.1% to about 10% by weight of the total composition.
Claim 3
Dependent Claim
14 words
The adhesive composition of claim 1, wherein the polymerizable cyanoacrylate monomer is ethyl cyanoacrylate.
Claim 4
Dependent Claim
31 words
The adhesive composition of claim 1, wherein the polymerizable acrylate ester monomer is allyl methacrylate, present in the amount of about 1% to about 5% by weight of the total composition.
Claim 5
Dependent Claim
21 words
The adhesive composition of claim 1, wherein the additive (c) is represented by the formula: ##STR12## wherein R 8 is phenyl.
Claim 6
Dependent Claim
23 words
The composition of claim 4, wherein the additive (c) is present in the amount of about 2% by weight of the total composition.
Claim 7
Dependent Claim
28 words
A composition as in claim 1 further comprising a free-radical polymerization inhibitor present in amounts of between about 0.1% to about 10% by weight of the total composition.
Claim 8
Dependent Claim
32 words
The adhesive composition of claim 6, wherein the free-radical polymerization inhibitor is selected from the group consisting of hydroquinones, benzoquinones, naphthoquinones, phenanthraquinones, anthraquinones, and a substituted compound of any of the foregoing.
Claim 9
Dependent Claim
27 words
The adhesive of claim 1, wherein the ionic polymerization inhibitor is a combination of sulfur dioxide and an acid having a pKa of between -12 and 7.
Claim 10
Dependent Claim
25 words
The adhesive composition of claim 8, wherein the acid is methane sulfonic acid in the range of 0.005% to 10% by weight of the composition.
Claim 11
Dependent Claim
21 words
The adhesive composition of claim 9, wherein the sulfur dioxide and methane sulfonic acid are present in the ratio of 20:50.
Claim 12
Dependent Claim
35 words
The adhesive composition of claim 1, wherein the polymerizable acrylate ester monomer component (b) is selected from the group consisting of allyl methacrylate, tetraethylene glycol dimethacrylate, triethylene glycol dimethacrylate, polyethylene glycol dimethacrylate and mixtures thereof.
Claim 13
Dependent Claim
37 words
The adhesive composition of claim 1, wherein the composition contains a sulfimide or a tertiary amine, present in the amount of about 0.1 to about 10% by weight of the composition, as an accelerator of free-radical polymerization.
Claim 14
Dependent Claim
28 words
An adhesive composition as in claim 1, wherein component (a) is ethyl cyanoacrylate, component (b) is allyl methacrylate, and component (c) is ##STR13## wherein R 8 is phenyl.
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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) | 1987-12-25 | 1988-06-25 | 1988-12-25 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-12-25 | 1992-06-25 | 1992-12-25 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-12-25 | 1996-06-25 | 1996-12-25 | $7700.00 | Window Closed / Lapsed |