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US3987019A
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Anaerobically hardening adhesives and sealants containing an organic sulfonyl hydrazones
Assignee: Henkel AG and Co KGaA
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Filing: 1975-08-25
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Granted: 1976-10-19
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Expires: 1995-08-25
Abstract
Abstract Organic sulfonyl hydrazones are accelerators for aerostable, anaerobically-setting adhesive compositions. They provide rapid setting of the adhesive with formation of bonds of good strength, and have little adverse effect upon the storage stability of the compositions when access of molecular oxygen is permitted.
Inventors
- 👤 Werner Gruber
- 👤 Joachim Galinke
- 👤 Jurgen Keil
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 22:07
CPC Classifications
C; C09; C09K; C09K3/00; C09K3/10; C09D; C09D5/00; C09D5/34; C09J; C09J4/00; C09K2003/1034; C09K2003/1065; C09K2200/00; C09K2200/04; C09K2200/0488; C09K2200/06; C09K2200/0615; C09K2200/0625; Y; Y10; Y10S; Y10S411/00; Y10S411/924; Y10S411/929; Y10S411/93; Y10T; Y10T428/00; Y10T428/31504; Y10T428/31678; Y10T428/31681; Y10T428/31692; Y10T428/31699
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
39 words
In an aerostable, anaerobically-setting adhesive composition comprising a polymerizable (meth) acrylate ester as principal latent adhesive component and a peroxide polymerization catalyst therefor: a small effective uniformly distributed amount of an organic sulfonyl hydrazone as accelerator for said catalyst.
Claim 2
Dependent Claim
39 words
In an aerostable, anaerobically-setting adhesive composition comprising a polymerizable (meth) acrylate ester as principal latent adhesive component and a peroxide polymerization catalyst therefor: a small effective uniformly distributed amount of an organic sulfonyl hydrazone as accelerator for said catalyst.
Claim 3
Dependent Claim
15 words
A composition according to claim 1 wherein the accelerator is methyl ethyl ketone tosyl hydrazone.
Claim 4
Dependent Claim
13 words
A composition according to claim 1 wherein the accelerator is acetone tosyl hydrazone.
Claim 5
Dependent Claim
13 words
A composition according to claim 1 wherein the accelerator is cyclohexanone tosyl hydrazone.
Claim 6
Dependent Claim
14 words
A composition according to claim 1 wherein the accelerator is acetoacetic ester tosyl hydrazone.
Claim 7
Dependent Claim
13 words
A composition according to claim 1 containing an organic amine as auxiliary accelerator.
Claim 8
Dependent Claim
13 words
A composition according to claim 6 wherein the auxiliary accelerator is N,N-dimethyl toluidine.
Claim 9
Dependent Claim
26 words
A composition according to claim 1 wherein the (meth) acrylate ester is the ester of two mols of methacrylic acid with one mole of ethylene glycol.
Claim 10
Dependent Claim
13 words
A composition according to claim 1 wherein the polymerization catalyst is a hydroperoxide.
Claim 11
Dependent Claim
13 words
A composition according to claim 1 wherein the polymerization catalyst is cumene hydroperoxide.
Claim 12
Dependent Claim
12 words
A composition according to claim 1 wherein the composition contains a stabilizer.
Claim 13
Dependent Claim
12 words
A composition according to claim 11 wherein the stabilizer is peracetic acid.
Claim 14
Dependent Claim
12 words
A composition according to claim 11 wherein the stabilizer is N-methyl-C-phenyl nitrone.
Claim 15
Dependent Claim
11 words
A composition according to claim 1 containing a free radical stabilizer.
Claim 16
Dependent Claim
13 words
A composition according to claim 14 wherein the free radical stabilizer is hydroquinone.
Claim 17
Independent Claim
49 words
A method for accelerating the setting rate of an aerostable, anaerobically-setting adhesive composition comprising a polymerizable (meth) acrylate ester as principal latent adhesive component and a peroxide polyermization catalyst therefor, which comprises uniformly incorporating in said composition a small but effective amount of an organic sulfonyl hydrazone as accelerator.
Claim 18
Independent Claim
49 words
A method for accelerating the setting rate of an aerostable, anaerobically-setting adhesive composition comprising a polymerizable (meth) acrylate ester as principal latent adhesive component and a peroxide polyermization catalyst therefor, which comprises uniformly incorporating in said composition a small but effective amount of an organic sulfonyl hydrazone as accelerator.
Claim 19
Dependent Claim
18 words
A method according to claim 16 wherein said hydrazone is incorporated in said composition prior to said catalyst.
Claim 20
Dependent Claim
28 words
A composition of matter according to claim 1, wherein the sulfonyl hydrazone is derived from aromatic sulfonic hydrazides having from 6 to 12 carbon atoms and a ketone.
Claim 21
Dependent Claim
86 words
A composition of matter according to claim 1, wherein the sulfonyl hydrazone is derived from aromatic sulfonic hydrazides having from 6 to 12 carbon atoms and the mono- and di- ring-halogenated derivatives thereof and a ketone selected from the group consisting of C 3 --C 30 alkanones, C 5 --C 8 cycloalkanones, C 8 --C 20 alkanoylbenzenes, C 12 --C 20 di-aromatic hydrocarbon ketones, C 5 --C 20 alkanediones, and lower alkanonates containing 4 to 8 carbon atoms and one ketonic group in the alkanonoate moiety.
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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) | 1979-10-19 | 1980-04-19 | 1980-10-19 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-10-19 | 1984-04-19 | 1984-10-19 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-10-19 | 1988-04-19 | 1988-10-19 | $7700.00 | Window Closed / Lapsed |