US4235986A
Expired / Lapsed
US
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Anaerobic curing adhesive composition and process for making same
Assignee: Ingredion Inc
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Filing: 1979-04-02
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Granted: 1980-11-25
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Expires: 1999-04-02
Abstract
Abstract Storage-stable anaerobic curing adhesive compositions useful as anaerobic adhesives and sealants are prepared by first mixing a polymerizable acrylate ester monomer, an inhibitor for free radical polymerization, a chelator, and at least an effective amount of an accelerator system consisting of an organic cyclic sulfimide, preferably saccharin, and an aromatic tertiary amine. The resultant homogeneous mixture is thereafter heated at a temperature of about 45°-100° C. for a period of time sufficient to provide the composition with anaerobic curing properties and a specified minimum amount of active oxygen. In one embodiment, the mixture is stirred at a temperature of 45°-70° C. for 10-24 hours. In another embodiment, the mixture is maintained at an elevated temperature without stirring.
Inventors
- 👤 William J. Catena
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 16:05
CPC Classifications
C; C09; C09J; C09J4/00
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
169 words
An improved process for preparing a storage-stable adhesive composition capable of curing in the absence of air which process comprises: (a) forming a homogeneous mixture consisting essentially of a polymerizable acrylate ester monomer, from 0.0001 to 0.1% by weight, based on monomer, of an inhibitor for free radical polymerization, from 0.0001 to 0.1% by weight, based on total composition, of a soluble chelator having ligand atoms other than nitrogen ligand atoms of the ≦C=N-type, this amount being dependent on the chelator, and at least an effective amount of an accelerator system consisting of an organic cyclic sulfimide and an aromatic tertiary amine; and (b) heating said mixture at a temperature of about 45°-100° C. for a period of time sufficient to provide said composition with anaerobic curing properties and to provide said composition with at least 25 ppm. active oxygen, said process not requiring the use of any externally added polymerization initiator and said process being conducted without constant passage of gaseous oxygen through the adhesive during preparation thereof.
Claim 2
Dependent Claim
169 words
An improved process for preparing a storage-stable adhesive composition capable of curing in the absence of air which process comprises: (a) forming a homogeneous mixture consisting essentially of a polymerizable acrylate ester monomer, from 0.0001 to 0.1% by weight, based on monomer, of an inhibitor for free radical polymerization, from 0.0001 to 0.1% by weight, based on total composition, of a soluble chelator having ligand atoms other than nitrogen ligand atoms of the ≦C=N-type, this amount being dependent on the chelator, and at least an effective amount of an accelerator system consisting of an organic cyclic sulfimide and an aromatic tertiary amine; and (b) heating said mixture at a temperature of about 45°-100° C. for a period of time sufficient to provide said composition with anaerobic curing properties and to provide said composition with at least 25 ppm. active oxygen, said process not requiring the use of any externally added polymerization initiator and said process being conducted without constant passage of gaseous oxygen through the adhesive during preparation thereof.
Claim 3
Dependent Claim
90 words
The process of claim 1 wherein said polymerizable monomer is ##STR11## wherein R is selected from the group consisting of hydrogen, methyl, ethyl, ##STR12## R' is selected from the group consisting of hydrogen, chlorine, methyl and ethyl; R" is selected from the group consisting of hydrogen, hydroxy, and ##STR13## m is an integer of from 1 to 8; n is an integer of from 1 to 20; and p is 0 or 1; or (b) monofunctional acrylate and methacrylate esters or the hydroxy-, amido-, cyano-, chloro-, or silane-substituted derivatives thereof.
Claim 4
Dependent Claim
19 words
The process of claim 2 wherein said polymerizable monomer is triethyleneglycol dimethacrylate, tetraethyleneglycol dimethacrylate, polyethyleneglycol dimethacrylate, or hydroxyethyl methacrylate.
Claim 5
Dependent Claim
11 words
The process of claim 1 wherein said sulfimide is o-benzoic sulfimide.
Claim 6
Dependent Claim
26 words
The process of claim 1 wherein said aromatic tertiary amine is selected from the group consisting of N,N-dimethylaniline, N,N-diethylaniline, p-isopropyl-N,N-dimethylaniline, N,N-dimethyl-p-toluidine, 2,4-dimethyl-N,N-dimethylaniline, 3,5-dimethyl-N,N-dimethylaniline, and mixtures thereof.
Claim 7
Dependent Claim
17 words
The process of claim 5 wherein said aromatic tertiary amine is a mixture of N,N-dimethyl-p-toluidine and N,N-diethylaniline.
Claim 8
Dependent Claim
16 words
The process of claim 1 wherein said chelator is oxalic acid or tetrasodium ethylenediamine tetraacetic acid.
Claim 9
Dependent Claim
37 words
The process of claim 1 wherein said sulfimide is present in an amount of 0.01 to 12% by weight and said amine is present in an amount of 0.01 to 3% by weight, based on total composition.
Claim 10
Dependent Claim
22 words
The process of claim 1 wherein said inhibitor is present in an amount of 0.0025 to 0.05% by weight, based on monomer.
Claim 11
Dependent Claim
23 words
The process of claim 1 wherein said chelator is present in an amount of 0.001 to 0.01% by weight, based on total composition.
Claim 12
Dependent Claim
15 words
The process of claim 1 wherein there is additionally present in said mixture a thickener.
Claim 13
Dependent Claim
19 words
The process of claim 1 wherein there is additionally present in said mixture a dye and a fluorescent agent.
Claim 14
Dependent Claim
17 words
The process of claim 1 wherein in step (b) said mixture is heated at about 45°-70° C.
Claim 15
Dependent Claim
24 words
The process of claim 1 wherein in step (b) said mixture is heated at said temperature for said period of time without stirring thereof.
Claim 16
Dependent Claim
24 words
The process of claim 1 wherein in step (b) said mixture is heated at said temperature for said period of time with stirring thereof.
Claim 17
Dependent Claim
19 words
The process of claim 15 wherein said mixture is heated at a temperature at 45°-70° C. for 10-24 hours.
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) | 1983-11-25 | 1984-05-26 | 1984-11-25 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-11-25 | 1988-05-26 | 1988-11-25 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-11-25 | 1992-05-26 | 1992-11-25 | $7700.00 | Window Closed / Lapsed |