Anaerobic curable compositions containing blocked dicarboxylic acid compounds

Patent metadata

Field	Value
Publication number	US-9828327-B2
Application number	US-201615340435-A
Country	US
Kind code	B2
Filing date	Nov 1, 2016
Priority date	May 1, 2014
Publication date	Nov 28, 2017
Grant date	Nov 28, 2017

Abstract

Anaerobic curable compositions, such as adhesives and sealants, containing blocked dicarboxylic acid compounds are provided. The blocked dicarboxylic acid compounds are labile dicarboxylic acid compounds having two acetal linkages, which cleave to release the underlying dicarboxylic acid during anaerobic cure. In this way, the dicarboxylic acid can participate in the anaerobic cure of the composition when the blocking group is released.

First claim

What is claimed is:

1. An anaerobic curable composition comprising;
(a) a (meth)acrylate component;
(b) an anaerobic cure system; and
(c) the reaction product of a vinyl ether compound and maleic acid.

2. The composition of claim 1 wherein the (meth)acrylate component is represented by: H 2 C=CGCO 2 R 1 , wherein G may be hydrogen, halogen, or alkyl groups having from 1 to about 4 carbon atoms, and R1 may be selected from alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkaryl, aralkyl, or aryl groups having from 1 to about 16 carbon atoms, any of which may be optionally substituted or interrupted as the case may be with silane, silicon, oxygen, halogen, carbonyl, hydroxyl, ester, carboxylic acid, urea, urethane, carbonate, amine, amide, sulfur, sulfonate and sulfone;
reaction products of the diglycidylether of bisphenol-A with methacrylic acid and a (meth)acrylate ester corresponding to structure as shown below:

wherein R 4 may be selected from hydrogen, alkyl groups having from 1 to about 4 carbon atoms, hydroxyalkyl groups having from 1 to about 4 carbon atoms or

R 5 may be selected from hydrogen, halogen, and alkyl groups of from 1 to about 4 carbon atoms;
R 6 may be selected from hydrogen, hydroxy and

m is an integer equal to at least 1;
v is 0 or 1; and
n is an integer equal to at least 1; and

polyfunctional (meth)acrylate monomers, di- or tri-functional (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)acrylate, diethylene glycol dimethacrylate, triethylene glycol dimethacrylate, tetraethylene glycol dimethacrylate, dipropylene glycol dimethacrylate, di-(pentamethylene glycol) dimethacrylate, tetraethylene diglycol diacrylate, diglycerol tetramethacrylate, tetramethylene dimethacrylate, ethylene dimethacrylate, neopentyl glycol diacrylate, trimethylol propane triacrylate, bisphenol-A mono and di(meth)acrylates, ethoxylated bisphenol-A (meth)acrylate, and bisphenol-F mono and di(meth)acrylates, and ethoxylated bisphenol-F (meth)acrylate.

3. The composition of claim 1 wherein the anaerobic cure system comprises a free-radical initiation and optimally one or more free-radical accelerators.

4. A composition comprising the reaction product of:
(a) a (meth)acrylate component;
(b) an anaerobic cure system; and
(c) the reaction product of a vinyl ether compound and maleic acid.

5. The composition of claim 1 wherein the vinyl ether compound is selected from one or more of ethyl vinyl ether; isobutyl vinyl ether; n-butyl vinyl ether; tert-butyl vinyl ether; cyclohexyl vinyl ether; 1,4-cyclohexane dimethanol divinyl ether; butanediol divinyl ether; hydroxybutyl vinyl ether; diethylene glycol divinyl ether; triethylene glycol divinyl ether; dodecyl vinyl ether; octadecyl vinyl ether; 4-(hydroxy methyl) cyclohexyl methyl vinyl ether; 2-ethyl hexyl vinyl ether; diethylene glycol monovinyl ether; poly-THF 290-divinyl ether; 3-amino propyl vinyl ether; tert-amyl vinyl ether; diethylaminoethyl vinyl ether; ethyleneglycol butyl vinyl ether; ethyleneglycol divinyl ether; ethyleneglycol monovinyl ether; hexanediol divinyl ether; hexanediol monovinyl ether; isopropyl vinyl ether; polyethyleneglycol-520 methyl vinyl ether; pluriol-E200 divinyl ether; n-propyl vinyl ether; tetraethyleneglycol divinyl ether; triethyleneglycol methyl vinyl ether; and trimethylolpropane trivinyl ether.

6. A method of making an anaerobic curable composition comprising;
(i) Providing a composition comprising:
(a) a (meth)acrylate component; and
(b) an anaerobic cure system; and

(ii) Adding to the composition of step (i)
the reaction product of a vinyl ether compound and maleic acid.

Assignees

• Henkel IP & Holding GmbH

Inventors

• Messana Andrew D
• Burdzy Sean M
• Schall Joel D
• Jacobine Anthony F

Classifications

• C09K3/1006

  characterised by the chemical nature of one of its constituents · CPC title

• C08F220/281

  and containing only one oxygen, e.g. furfuryl (meth)acrylate or 2-methoxyethyl (meth)acrylate · CPC title

• C08F220/286

  and containing polyethylene oxide in the alcohol moiety, e.g. methoxy polyethylene glycol (meth)acrylate · CPC title

• C09K2200/0625

  Polyacrylic esters or derivatives thereof · CPC title

• C09J133/14

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