US4005055A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Anaerobic aminimide curing compositions
Assignee: Skeist Lab Inc
•
Filing: 1975-05-22
•
Granted: 1977-01-25
•
Expires: 1995-05-22
Abstract
Abstract Anaerobic curing compositions are provided which comprise an alpha-olefinically substituted aminimide and an organic hydroperoxide as a sealant composition having extended shelf life in the presence of oxygen and being rapidly polymerizable upon the exclusion of oxygen.
Inventors
- 👤 Jerry Miron
- 👤 Manilal Savla
- 👤 Irving Skeist
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 17:14
CPC Classifications
G; G01; G01L; G01L5/00; G01L5/0061; C; C09; C09J; C09J4/00
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
150 words
A sealant composition having extended shelf life in the presence of oxygen and being rapidly polymerizable upon the exclusion of oxygen which comprises a mixture of an unoxygenated aminimide monomer selected from the group consisting of (A) hydroxy substituted aminimides corresponding to the general formula [CH 2 =CR--CO--N ---N + (R 1 R 2 ]n --R 3 , wherein n is an integer having a value of 1 or 2, R is hydrogen, loweralkyl, fluorine, chlorine, bromine or a cyano group, R 1 and R 2 are each loweralkyl radicals, R 3 is selected from the group consisting of hydroxyalkyl and substituted hydroxyalkyl radicals and (B) modified aminimides produced by reaction of the aminimides of (A) with reactants of the group consisting of organic isocyanates, epoxides, organic acids and anhydrides; with from about 0.01 to about 20% by weight, based on the weight of the composition, of an organic hydroperoxide.
Claim 2
Dependent Claim
150 words
A sealant composition having extended shelf life in the presence of oxygen and being rapidly polymerizable upon the exclusion of oxygen which comprises a mixture of an unoxygenated aminimide monomer selected from the group consisting of (A) hydroxy substituted aminimides corresponding to the general formula [CH 2 =CR--CO--N ---N + (R 1 R 2 ]n --R 3 , wherein n is an integer having a value of 1 or 2, R is hydrogen, loweralkyl, fluorine, chlorine, bromine or a cyano group, R 1 and R 2 are each loweralkyl radicals, R 3 is selected from the group consisting of hydroxyalkyl and substituted hydroxyalkyl radicals and (B) modified aminimides produced by reaction of the aminimides of (A) with reactants of the group consisting of organic isocyanates, epoxides, organic acids and anhydrides; with from about 0.01 to about 20% by weight, based on the weight of the composition, of an organic hydroperoxide.
Claim 3
Dependent Claim
32 words
The composition of claim 1 wherein in (A) R 3 is selected from the group consisting of hydroxyalkyl, oxy-bis-hydroxyalkyl, alkylene-bis-oxyhydroxyalkyl, acryloxyhydroxyalkyl, alkoxyhydroxyalkyl, methacryloxyhydroxyalkyl, allyloxyhydroxyalkyl, vinyloxyhydroxyalkyl and polyoxyalkyl - bis - hydroxyalkyl radicals.
Claim 4
Dependent Claim
17 words
The composition of claim 2 wherein the unoxygenated aminimide monomer contains at least two alpha-olefinic polymerization sites.
Claim 5
Dependent Claim
28 words
The composition of claim 3 which comprises additionally an organic tertiary amine in an amount from 0.1 to 10% by weight, based on the weight of the composition.
Claim 6
Dependent Claim
25 words
The composition of claim 4 wherein the tertiary amine is selected from the group consisting of N,N-dimethylaniline, dimethylethanolamine, N,N-dimethyl-m-toluidine, N,N-dimethyl-p-toluidine, triethylamine, tripropylamine, tributylamine and triamylamine.
Claim 7
Dependent Claim
45 words
The composition of claim 3 which comprises additionally an agent selected from the group consisting of organic imides and metal salts of organic imides, formamide and N-substituted formamide in an amount from about 0.05 to 5% by weight, based on the weight of the composition.
Claim 8
Dependent Claim
29 words
The composition of claim 6 wherein the agent is selected from the group consisting of o-benzoic sulfimide, succinimide, phthalimide, formamide, N-methylformamide, N-ethylformamide and the sodium salt of o-benzoic sulfimide.
Claim 9
Dependent Claim
19 words
The composition of claim 7 wherein the agent is selected from the group consisting of o-benzoic sulfimide and formamide.
Claim 10
Dependent Claim
30 words
The composition of claim 3 which comprises additionally an inhibitor selected from the group consisting of phenolic and quinone compounds in an amount of 10 to 1000 parts per million.
Claim 11
Dependent Claim
24 words
The composition of claim 9 wherein the inhibitor is selected from the group consisting of 2,6-ditertiary butyl-p-cresol, 1,4-benzoquinone, 2,5-dihydroxy -1,4 benzoquinone, 1,2-naphthoquinone and 9,10-anthraquinone.
Claim 12
Dependent Claim
20 words
The composition of claim 10 wherein the inhibitor is selected from the group consisting of 2,6-ditertiary butyl-p-cresol 1,4-benzoquinone and 2,5-dihydroxy-1,4-benzoquinone.
Claim 13
Dependent Claim
45 words
The composition of claim 3 wherein the aminimide monomer corresponds to A wherein n is 1, R is hydrogen or loweralkyl, R 1 and R 2 are each loweralkyl and R 3 is selected from the group consisting of vinyloxyhydroxyalkyl, allylhydroxyalkyl, acryloxyhydroxyalkyl and methacryloxyalkyl radicals.
Claim 14
Dependent Claim
33 words
The composition of claim 12 wherein R, R 1 , and R 2 , are each a methyl radical and R 3 is selected from the group consisting of allylhydroxyalkyl and methacryloxyalkyl radicals.
Claim 15
Dependent Claim
38 words
The composition of claim 3 wherein the aminimide monomer corresponds to A wherein n is 2, R is hydrogen or lower alkyl, R 1 and R 2 are each lower alkyl and R 3 is an alkylene-bis-oxyhydroxyalkyl radical.
Claim 16
Dependent Claim
36 words
The composition of claim 14 wherein R, R 1 and R 2 are each a methyl radical and R 3 is -- CH 2 -- CHOH--CH 2 --O--(CH 2 ) 4 --O--CH 2 --CHOH--CH 2 --.
Claim 17
Dependent Claim
27 words
The composition of claim 3 wherein the aminimide monomer comprises a hydroxy substituted aminimide corresponding to A which has been modified by reaction with an organic isocyanate.
Claim 18
Dependent Claim
11 words
The composition of claim 16 wherein the isocyanate is toluene diisocyanate.
Claim 19
Dependent Claim
62 words
The composition of claim 17 wherein n is 1, R, R 1 , and R 2 of the aminimide are each a methyl radical and R 3 is selected from the group consisting of --CH 2 --CHOH--CH 3 , --CH 2 --O--CH 2 --CH=CH 2 , --CH 2 --CHOH--CH 2 --O--CO--C(CH 3 )=CH 2 and --CH 2 --CHOH--CH 2 --O--CO--CH=CH 2 radicals.
References Cited (Backward Citations)
US3428614A
Cited
US3664990A
Cited
US3756994A
Cited
US3720656A
Cited
US3775385A
Cited
US3728387A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-01-25 | 1980-07-26 | 1981-01-25 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-01-25 | 1984-07-26 | 1985-01-25 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-01-25 | 1988-07-26 | 1989-01-25 | $7700.00 | Window Closed / Lapsed |