Cure accelerators for anaerobic curable compositions

Patent metadata

Field	Value
Publication number	US-11274190-B2
Application number	US-202016844279-A
Country	US
Kind code	B2
Filing date	Apr 9, 2020
Priority date	Oct 9, 2017
Publication date	Mar 15, 2022
Grant date	Mar 15, 2022

Abstract

The present invention relates to cure accelerators useful for anaerobic curable compositions, such as adhesives and sealants. The cure accelerators are embraced withinwhere X is CH2, O, S, NR4, CR5R6 or C═O, wherein R4, R5, and R6 are each individually selected from hydrogen, halogen, amino, carboxyl, nitro, alkyl, alkenyl, alkynyl, hydroxyalkyl, hydroxyalkenyl, hydroxyalkynyl, or alkaryl; R is one or more of hydrogen, alkyl, alkenyl, alkynl, hydroxyalkyl, hydroxyalkenyl, or hydroxyalkynl; R1, R2, and R3 are each individually selected from hydrogen, halogen, amino, carboxyl, nitro, alkyl, alkenyl, alkynyl, hydroxyalkyl, hydroxyalkenyl, hydroxyalkynyl, or alkaryl; R7 is hydrogen or CHR8R9, where R8 and R9 are each individually selected from hydrogen, halogen, amino, carboxyl, nitro, alkyl, alkenyl, alkynyl, hydroxyalkyl, hydroxyalkenyl, hydroxyalkynyl, or alkaryl; and n is 0 or 1. A particularly desirable example is 1,2,3,4-tetrahydrobenzo-h-quinolin-3-ol.

First claim

What is claimed is:

1. An anaerobic curable composition comprising:
(a) a (meth)acrylate component;
(b) an anaerobic cure-inducing composition; and
(c) a cure accelerator embraced by

wherein X is CH 2 , O, S, NR 4 , CR 5 R 6 or C═O, wherein R 4 , R 5 , and R 6 are each individually selected from hydrogen, halogen, amino, carboxyl, nitro, alkyl, alkenyl, alkynyl, hydroxyalkyl, hydroxyalkenyl, hydroxyalkynyl, or alkaryl; R is hydrogen, alkyl, alkenyl, alkynl, hydroxyalkyl, hydroxyalkenyl, or hydroxyalkynl; R 1 , R 2 , and R 3 are each individually selected from hydrogen, halogen, amino, carboxyl, nitro, alkyl, alkenyl, alkynyl, hydroxyalkyl, hydroxyalkenyl, hydroxyalkynyl, or alkaryl; R 7 is hydrogen or CHR 8 R 9 , wherein R 8 and R 9 are each individually selected from hydrogen, halogen, amino, carboxyl, nitro, alkyl, alkenyl, alkynyl, hydroxyalkyl, hydroxyalkenyl, hydroxyalkynyl, or alkaryl; and n is 0 or 1.

2. The composition according to claim 1 , wherein the anaerobic cure-inducing composition comprises a hydroperoxide selected from the group consisting of t-butyl hydroperoxide, p-methane hydroperoxide, cumene hydroperoxide, diisopropylbenzene hydroperoxide, and mixtures thereof.

3. The composition according to claim 1 , further comprising at least one co-accelerator.

4. The composition according to claim 3 , wherein the co-accelerator is selected from the group consisting of amines, amine oxides, sulfonamides, metal sources, acids, and mixtures thereof.

5. The composition according to claim 3 , wherein the co-accelerator is selected from the group consisting of triazines, ethanolamine, diethanolamine, triethanolamine, N,N dimethyl aniline, benzene sulphanimide, cyclohexyl amine, triethyl amine, butyl amine, saccharin, N,N-diethyl-p-toluidine, N,N-dimethyl-o-toluidine, acetyl phenylhydrazine, maleic acid, and mixtures thereof.

6. The composition according to claim 1 , further comprising at least one stabilizer.

7. The composition according to claim 6 , wherein the stabilizer is selected from the group consisting of benzoquinone, naphthoquinone, anthraquinone, hydroquinone, methoxyhydroquinone, butylated hydroxy toluene, ethylene diamine tetraacetic acid or a salt thereof, and mixtures thereof.

8. The composition according to claim 1 , wherein the cure accelerator is

wherein R is hydrogen, alkyl, alkenyl, alkynl, hydroxyalkyl, hydroxyalkenyl, or hydroxyalkynl; and R 1 and R 2 are each individually selected from halogen, amino, carboxyl, nitro, alkyl, alkenyl, alkynyl, hydroxyalkyl, hydroxyalkenyl, hydroxyalkynyl, or alkaryl.

9. The composition according to claim 1 , wherein the cure accelerator is selected from one or more of

wherein R, R 1 and R 2 are as defined above.

10. The composition according to claim 1 , wherein the cure accelerator is

1,2,3,4-tetrahydrobenzo-h-quinolin-3-ol.

Assignees

• Henkel IP & Holding GmbH
• Henkel Ag & Co Kgaa

Inventors

• Birkett David
• O'Dwyer Pat
• Condron David
• Mongey Hilary

Classifications

• C08K5/08

  Quinones · CPC title

• C09J4/00 Primary

  Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond {; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16} · CPC title

• C09J133/14

  of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen · CPC title

• C08F20/20 Primary

  of polyhydric alcohols or {polyhydric} phenols {, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate} · CPC title

• C08K5/0025

  Crosslinking or vulcanising agents; including accelerators · CPC title