US4373077A
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Anaerobically curing compositions
Assignee: 3M Co
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Filing: 1981-08-03
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Granted: 1983-02-08
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Expires: 2001-08-03
Abstract
Abstract Anaerobically-curing compositions are described which are free of peroxy initiators and inorganic salt initiators and which comprise (A) a polymerizable monomer; (B) as a first initiator component, a compound selected from the group consisting of organic sulfimide and perfluoroalkyl sulfonanilides; (C) as a second initiator component, a secondary or tertiary aromatic amine; and (D) a diaryl N-nitrosamine as a polymerization inhibitor. Methods are also described for stabilizing anaerobically-curing compositions through inclusion therein of a diaryl N-nitrosamine. The compositions are particularly suitable as adhesives and may be formulated as thread-locking adhesives or may be modified by the addition of various modifying polymers to obtain desired properties such as increased viscosities of pressure-sensitive properties.
Inventors
- 👤 Charles W. Boeder
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 01:47
CPC Classifications
C; C09; C09J; C09J4/00
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
98 words
An anaerobically-curing composition free of peroxy intiators and inorganic salt initiators, said composition comprising: (A) 100 parts by weight of a polymerizable monomer having at least one α,β-unsaturated carboxyl functionality per molecule of monomer; (B) as a first initiator component, about 0.1 to 20 parts by weight of a compound selected from the group consisting of organic sulfimides and perfluoroalkyl sulfonanilides; (C) as a second initiator component, about 0.05 to 20 parts by weight of a secondary or tertiary aromatic amine; and (D) as a polymerization inhibitor, about 0.01 to 3 parts by weight of a diaryl N-nitrosamine.
Claim 2
Dependent Claim
98 words
An anaerobically-curing composition free of peroxy intiators and inorganic salt initiators, said composition comprising: (A) 100 parts by weight of a polymerizable monomer having at least one α,β-unsaturated carboxyl functionality per molecule of monomer; (B) as a first initiator component, about 0.1 to 20 parts by weight of a compound selected from the group consisting of organic sulfimides and perfluoroalkyl sulfonanilides; (C) as a second initiator component, about 0.05 to 20 parts by weight of a secondary or tertiary aromatic amine; and (D) as a polymerization inhibitor, about 0.01 to 3 parts by weight of a diaryl N-nitrosamine.
Claim 3
Dependent Claim
72 words
A composition in accordance with claim 1, wherein said monomer is selected from the group consisting of triethyleneglycol dimethacrylate, ethyleneglycol dimethacrylate, tetraethyleneglycol dimethacrylate, polyethyleneglycol dimethacrylate, polyethyleneglycol diacrylate, 1,3-buryleneglycol dimethacrylate, trimethylol propane trimethacrylate, neopentylglycol dimethacrylate, ethoxylated bisphenol A dimethacrylate, propoxylated bisphenol C dimethacrylate, bisphenol A bis (2-hydroxypropyl)dimethacrylate, cyclohexyl methacrylate, 2-ethylhexyl methacrylate, hydroxyethyl methacrylate, isooctyl acrylate, n-butyl acrylate, methacrylic acid, the 2-hydroxyethyl methacrylate half-ester of maleic acid, and monomeric polyacrylate esters formed from isocyanates.
Claim 4
Dependent Claim
34 words
A composition in accordance with claim 1, wherein said first initiator component is a sulfimide of the formula ##STR8## wherein: R 1 and R 2 are organic radicals comprising up to about 10 carbons.
Claim 5
Dependent Claim
21 words
A composition in accordance with claim 3, wherein said sulfimide is selected from the group consisting of o-benzoic sulfimide and ##STR9##
Claim 6
Dependent Claim
17 words
A composition in accordance with claim 1, wherein said first initiator component initiator is a perfluoroalkyl sulfonanilide.
Claim 7
Dependent Claim
24 words
A composition in accordance with claim 5, wherein said perfluoroalkyl sulfonanilide is selected from the group consisting of trifluoromethanesulfonanilide, 4-trifluoromethyltrifluoromethanesulfonanilide, 2-phenyltrifluoromethanesulfonanilide, 4-phenylthiotrifluoromethanesulfonanilide and N-2-naphthyltrifluoromethylsulfonanilide.
Claim 8
Dependent Claim
92 words
A composition in accordance with claim 1, wherein said amine is a tertiary aromatic amine of the formula: ##STR10## wherein: R 3 and R 4 are each hydrocarbon groups comprising up to about 12 carbons; A is a carbocyclic aromatic nucleus selected from the group consisting of unsubstituted phenyl radicals, substituted phenyl radicals, unsubstituted naphthyl radicals and substituted naphthyl radicals; R 5 is an organic radical comprising up to about 5 carbons and is selected from the group consisting of alkyl and alkoxy radicals; and t is from 0 to 3 inclusive.
Claim 9
Dependent Claim
28 words
A composition in accordance with claim 1, wherein said second initiator component is selected from the group consisting of N,N-dimethyl-p-toluidine, N,N-diethyl-p-toluidine, N,N-dimethylaniline, N,N-dimethyl-p-anisidine, N,N-diethylaniline, N,N-diethylaniline, N,N-bis-(2-hydroxyethyl)-p-toluidine and 1,2,3,4-tetrahydroquinoline.
Claim 10
Dependent Claim
24 words
A composition in accordance with claim 1, wherein said polymerization initiator comprises the amine-salt of said first initiator component and said second initiator component.
Claim 11
Dependent Claim
41 words
A composition in accordance with claim 1, wherein said diaryl N-nitrosamine is of the formula ##STR11## wherein: R 5 and R 6 are each a carbocyclic aromatic nucleus selected from the group consisting of unsubstituted or substituted phenyl and naphthyl radicals.
Claim 12
Dependent Claim
20 words
A composition in accordance with claim 10, wherein said N-nitrosamine is selected from the group consisting of N-nitrosodiphenylamine and 2-naphthyl-phenyl-N-nitrosamine.
Claim 13
Dependent Claim
26 words
A composition in accordance with claim 1, wherein said first initiator component is o-benzoic sulfimide, said second initiator component is N,N-dimethyl-p-toluidine and said N-nitrosamine is N-nitrosodiphenylamine.
Claim 14
Dependent Claim
58 words
A composition in accordance with claim 1, wherein said first initiator component is present in an amount of about 0.5 to 5 parts by weight, said second initiator component is present in an amount of about 0.2 to 5 parts by weight and said N-nitrosamine is present in an amount of about 0.02 to 1 parts by weight.
Claim 15
Independent Claim
121 words
A method for stabilizing an anaerobically-curing composition during storage in the presence of air, said method comprising including in said composition a diaryl N-nitrosamine, wherein said composition comprises: (A) 100 parts by weight of a polymerizable monomer having at least one α,β-unsaturated carboxyl functionality per molecule of monomer; (B) as a first initiator component, about 0.1 to 20 parts by weight of a compound selected from the group consisting of organic sulfimides and perfluoroalkyl sulfonanilides; and (C) as a second initiator component, about 0.05 to 20 parts by weight of a secondary or tertiary aromatic amine; and wherein said N-nitrosamine is included in an amount of about 0.01 to 3 parts by weight per 100 parts by weight of said monomer.
Claim 16
Independent Claim
121 words
A method for stabilizing an anaerobically-curing composition during storage in the presence of air, said method comprising including in said composition a diaryl N-nitrosamine, wherein said composition comprises: (A) 100 parts by weight of a polymerizable monomer having at least one α,β-unsaturated carboxyl functionality per molecule of monomer; (B) as a first initiator component, about 0.1 to 20 parts by weight of a compound selected from the group consisting of organic sulfimides and perfluoroalkyl sulfonanilides; and (C) as a second initiator component, about 0.05 to 20 parts by weight of a secondary or tertiary aromatic amine; and wherein said N-nitrosamine is included in an amount of about 0.01 to 3 parts by weight per 100 parts by weight of said monomer.
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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) | 1986-02-07 | 1986-08-09 | 1987-02-08 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-02-07 | 1990-08-09 | 1991-02-08 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-02-07 | 1994-08-09 | 1995-02-08 | $7700.00 | Window Closed / Lapsed |