Patent US4096323A successfully refreshed from Google Patents.
US4096323A
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Anaerobically hardening adhesives and sealants based on (meth)acrylic esters containing reaction products of glycidyl(meth)acrylate and half esters of dicarboxylic acids
Assignee: Henkel AG and Co KGaA
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Filing: 1977-02-22
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Granted: 1978-06-20
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Expires: 1997-02-22
Abstract
Abstract Reaction products of glycidyl (meth)acrylate with linear half esters of dicarboxylic acids are components of anaerobically-setting adhesive compositions based on (meth)acrylic esters and organic peroxides.
Inventors
- 👤 Bernd Wegemund
- 👤 Werner Gruber
- 👤 Joachim Galinke
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 03:23
CPC Classifications
C; C09; C09J; C09J4/00
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
122 words
An anaerobically setting adhesive and sealing composition comprising methacrylic- or acrylic esters, organic hydroperoxides, and optionally small amounts of additional polymerizable, unsaturated compounds, and ordinary auxiliary substances, which contain 10 to 90% by weight, based on the total weight of the polymerizable portions of the composition, of condensation reaction products of glycidyl (meth)acrylate with linear half esters of dicarboxylic acids and diols, prepared by esterification of dicarboxylic acids or dicarboxylic acid derivatives with diols in the molar ratio of 2:1, which reaction products of glycidyl (meth) acrylate with linear half esters are substantially free of epoxide groups, wherein more than 1 mole of glycidyl (meth) acrylate is reacted per mole of the linear half ester of a dicarboxylic acid and a diol.
Claim 2
Dependent Claim
122 words
An anaerobically setting adhesive and sealing composition comprising methacrylic- or acrylic esters, organic hydroperoxides, and optionally small amounts of additional polymerizable, unsaturated compounds, and ordinary auxiliary substances, which contain 10 to 90% by weight, based on the total weight of the polymerizable portions of the composition, of condensation reaction products of glycidyl (meth)acrylate with linear half esters of dicarboxylic acids and diols, prepared by esterification of dicarboxylic acids or dicarboxylic acid derivatives with diols in the molar ratio of 2:1, which reaction products of glycidyl (meth) acrylate with linear half esters are substantially free of epoxide groups, wherein more than 1 mole of glycidyl (meth) acrylate is reacted per mole of the linear half ester of a dicarboxylic acid and a diol.
Claim 3
Dependent Claim
66 words
The composition according to claim 1 which contains 10 to 40% by weight, based on the total weight of the polymerizable portions of the composition, of cycloaliphatic, heterocyclic, or aliphatic (meth)acrylic acid esters, which are optionally substituted by hydroxy groups and 60% to 90% by weight, based on the total weight of the polymerizable portions of the composition, of the other polymerizable portions of said composition.
Claim 4
Dependent Claim
51 words
The composition according to claim 1 wherein the half esters of dicarboxylic acids are derived from the reaction of a short straight- or branched-chain, saturated or unsaturated aliphatic diol or diols with aliphatic, cycloaliphatic, or aromatic dicarboxylic acids or acid anhydrides, the ratio of diol:acid or acid anhydride being about 1:2.
Claim 5
Dependent Claim
23 words
The composition according to claim 1 wherein the molar ratio of glycidyl (meth) acrylate to linear half ester is about 2 to 1.
Claim 6
Dependent Claim
35 words
The composition according to claim 3 wherein the diols are selected from the group consisting of alkanediols, alkenediols, or alkynediols, or any combination of said diols, said diols having from 2 to 8 carbon atoms.
Claim 7
Dependent Claim
31 words
The composition according to claim 2 which contains from 0 to 5% by weight, based on the total weight of the polymerizable portions of the composition, of a polymerizable carboxylic acid.
Claim 8
Dependent Claim
23 words
The composition according to claim 6 wherein the polymerizable carboxylic acid is selected from the group consisting of methacrylic acid and acrylic acid.
Claim 9
Dependent Claim
24 words
The composition according to claim 1 which additionally contains 0.05 to 3.0% by weight, based on the weight of (meth)acrylic esters, of a stabilizer.
Claim 10
Dependent Claim
12 words
The composition according to claim 8 wherein the stabilizer is peracetic acid.
Claim 11
Dependent Claim
13 words
The composition according to claim 1 which additionally contains an accelerator or accelerators.
Claim 12
Dependent Claim
16 words
The composition according to claim 1 which additionally contains an accelerator or accelerators and a stabilizer.
Claim 13
Dependent Claim
15 words
The composition according to claim 11 which contains p-toluenesulfonic acid hydrazide, N,N-dimethyl-p-toluidine and peracetic acid.
Claim 14
Dependent Claim
12 words
The composition according to claim 1 wherein the hydroperoxide is cumene hydroperoxide.
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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) | 1981-06-19 | 1981-12-19 | 1982-06-20 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-06-19 | 1985-12-19 | 1986-06-20 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-06-19 | 1989-12-19 | 1990-06-20 | $7700.00 | Window Closed / Lapsed |