# US 7,411,025 B1 · Cure accelerators for anaerobic curable compositions

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- Number: US 7,411,025 B1
- Document ID: US7411025B1
- Status: Granted
- Kind: B1
- Application number: 11/084,118
- Filed: 2005-03-21
- Granted: 2008-08-12
- Earliest claimed: 2003-12-22
- Assignees: Henkel Corporation
- Inventors: Andrew D. Messana; Philip T. Klemarczyk; Karen R. Brantl
- Web page: https://patentgrep.com/patent/US7411025B1

## CPC

- C09J 11/06: organic
- C09D 133/06: of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09J 133/14: of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
- C08L 33/00: Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C09J: ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES (preparation of glue or gelatine C09H)
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)

## Abstract

The present invention relates to phenylgycines and derivatives thereof, 1,4-aminobenzoyl compounds, and phenyl pyrazolinones as cure accelerators for anaerobically curable compositions.

## Claims

### Claim 1

An anaerobic curable composition, comprising:
(a) a (meth)acrylate component; and
(b) an anaerobic cure-inducing composition comprising an anaerobic cure accelerator compound within structure I
wherein R appears up to five times on the phenyl ring and is independently selected from the group consisting of hydrogen, halogen, alkenyl, hydroxyalkyl, hydroxyalkenyl, or sulfonato; R1 is selected from the group consisting of hydrogen, alkyl, alkenyl, hydroxyalkyl, hydroxyalkenyl, aralkyl, carbonyl or carboxyl; and R2 is selected from the group consisting of hydrogen, alkyl, alkenyl, hydroxyalkyl, hydroxyalkenyl, aralkyl, nitrogen, carbonyl and carboxyl.

### Claim 2 (depends on 1)

The composition according to claim 1, wherein the (meth)acrylate component is represented by H2C═CGCO2R1, wherein G is a member selected from the group consisting of H, halogen and alkyl having from 1 to about four carbon atoms, and R1 is a member selected from the group consisting of alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkaryl, and aryl groups having from 1 to about 16 carbon atoms, with or without substitution or interruption by a member selected from the group consisting of silane, silicon, oxygen, halogen, carbonyl, hydroxyl, ester, carboxylic acid, urea, urethane, carbamate, amine, amide, sulfur, sulonate and sulfone.

### Claim 3 (depends on 1)

The composition according to claim 1, wherein the (meth)acrylate component is a member selected from the group consisting of silicone (meth)acrylates, polyethylene glycol di(meth)acrylates, bisphenol-A-(meth)acrylates, ethoxylated bisphenol-A-(meth)acrylates, bisphenol-F-(meth)acrylates, ethoxylated bisphenol-F-(meth)acrylates, tetrahydrofuran (meth)acrylates and di(meth)acrylates, hydroxypropyl (meth)acrylate, hexanediol di(meth)acrylate, and trimethylol propane tri(meth)acrylate.

### Claim 4 (depends on 1)

The composition according to claim 1, wherein the anaerobic cure accelerator is a member selected from the group consisting of N-phenyl glycine, N-methyl-N-phenyl glycine, ethyl-4-(dimethylamino) benzoate, and combinations thereof.

### Claim 5 (depends on 1)

The composition according to claim 1, further comprising an additional accelerator.

### Claim 6 (depends on 1)

The composition according to claim 1, further comprising a peroxide compound.

### Claim 7 (depends on 5)

The composition according to claim 5, wherein the additional accelerator is saccharin.

### Claim 8 (depends on 1)

A method of preparing an anaerobic curable composition, comprising the step of:
mixing together:
a (meth)acrylate component, and
an anaerobic cure inducing composition comprising an anaerobic cure accelerator compound in accordance with claim 1.