Phenylhydrazine/anhydride adducts and anaerobic curable compositions using same

Patent metadata

Field	Value
Publication number	US-10662147-B2
Application number	US-201715485546-A
Country	US
Kind code	B2
Filing date	Apr 12, 2017
Priority date	Oct 22, 2014
Publication date	May 26, 2020
Grant date	May 26, 2020

Abstract

Phenylhydrazine/anhydride adducts and anaerobic curable compositions using these adducts are provided. The compositions are particularly useful as adhesives and sealants.

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 compound of Structure I

wherein:
R 1 is selected from the group consisting of H and C 1-4 alkyl;
p is an integer between 1 and 5; and
the cycloaliphatic ring represents a cycloalkyl, cycloalkenyl, bicycloalkyl or bicycloalkenyl, with or without one or more C 1-4 alkyl substituents.

2. The composition according to claim 1 , wherein the compound is a member selected from the group consisting of:

3. The composition according to claim 1 , wherein the (meth)acrylate component is shown by H 2 C═CGCO 2 R 10 , wherein G is a member selected from the group consisting of H, halogen and alkyl having from 1 to about four carbon atoms, and R 10 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, sulfonate and sulfone.

4. 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, tetrahydrofuran (meth)acrylates and di(meth)acrylates, hydroxypropyl (meth)acrylate, hexanediol di(meth)acrylate, trimethylol propane tri(meth)acrylates, diethylene glycol di(meth)acrylates, triethylene glycol di(meth)acrylates, tetraethylene diglycol di(meth)acrylates, diglycerol tetra(meth)acrylates, tetramethylene di(meth)acrylates, ethylene di(meth)acrylates, neopentyl glycol di(meth)acrylates, bisphenol-A-(meth)acrylates, ethoxylated bisphenol-A-(meth)acrylates, bisphenol-F-(meth)acrylates, ethoxylated bisphenol-F-(meth)acrylates, and bisphenol-A di(meth)acrylates, ethoxylated bisphenol-A-di(meth)acrylates, bisphenol-F-di(meth)acrylates, and ethoxylated bisphenol-F- di(meth)acrylates.

5. The composition according to claim 1 , further comprising a co-accelerator.

6. A process for curing an anaerobic curable composition, comprising the steps of: applying an anaerobic curable composition according to claim 1 , to a desired substrate surface; and exposing the composition to an anaerobic environment for a time sufficient to cure the composition.

7. A method of preparing an anaerobic curable composition, comprising the step of:
mixing together:
i) as an anaerobic cure accelerator, a compound having Structure I

wherein:
R 1 is selected from the group consisting of H and C 1-4 alkyl;
p is an integer between 1 and 5; and
the cycloaliphatic ring represents a cycloalkyl, cycloalkenyl, bicycloalkyl or bicycloalkenyl, with or without one or more C 1-4 alkyl substituents;
(ii) a (meth)acrylate component; and
(iii) an anaerobic cure-inducing composition.

8. The composition according to claim 1 , wherein the anaerobic cure-inducing composition comprises the combination of a free radical initiator and a free radical co-accelerator.

9. A method of using a compound of Structure I

wherein:
R 1 is selected from the group consisting of H and C 1-4 alkyl;
p is an integer between 1 and 5; and
the cycloaliphatic ring represents a cycloalkyl, cycloalkenyl, bicycloalkyl or bicycloalkenyl, with or without one or more C 1-4 alkyl substituents, as an anaerobic cure accelerator comprising the step of either: (I) mixing the compound with a (meth)acrylate component, an anaerobic cure inducing composition, or (II) applying onto a surface of a substrate the compound and applying thereover an anaerobic curable composition.

10. The composition of claim 1 , further comprising acrylic acid.

Assignees

• Henkel IP & Holding GmbH

Inventors

• Klemarczyk Philip T
• Birkett David P

Classifications

• C09J133/10

  Homopolymers or copolymers of methacrylic acid esters · CPC title

• C07C243/36 Primary

  with acylating carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings · CPC title

• C07C2601/14

  The ring being saturated · CPC title

• C07C2601/16

  the ring being unsaturated · CPC title

• C07C2602/42

  the bicyclo ring system containing seven carbon atoms · CPC title