ANAEROBIC CURABLE COMPOSITIONS CONTAINING BLOCKED DICARBOXYLIC ACID COMPOUNDS

• US 20170044089A1
• Filed: 11/01/2016
• Published: 02/16/2017
• Est. Priority Date: 05/01/2014
• Status: Active Grant

• Current Assignee: Henkel AG & Co KGaA
• Original Assignee: Henkel IP & Holding GmbH (Henkel AG & Co KGaA)
• Inventors: Messana, Andrew D., Burdzy, Sean M., Schall, Joel D., Jacobine, Anthony F.
• Granted Patent: US 9,828,327 B2
• Time in Patent Office: Days
• CPC Class Codes: C07C 69/54 Acrylic acid esters; Methacrylic acid esters
• CPC Class Codes: C07C 69/60 Maleic acid esters; Fumaric acid esters
• CPC Class Codes: C08F 2/44 Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
• CPC Class Codes: C08F 220/281 and containing only one oxygen, e.g. furfuryl (meth)acrylate or 2-methoxyethyl (meth)acrylate
• CPC Class Codes: C08F 220/286 and containing polyethylene oxide in the alcohol moiety, e.g. methoxy polyethylene glycol (meth)acrylate
• CPC Class Codes: C08F 222/02 Acids; Metal salts or ammonium salts thereof , e.g. maleic acid or itaconic acid
• CPC Class Codes: C08F 222/06 Maleic anhydride
• CPC Class Codes: C08F 265/06 Polymerisation of acrylate or methacrylate esters on to polymers thereof
• CPC Class Codes: C08L 33/06 of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
• CPC Class Codes: C09J 133/06 of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
• CPC Class Codes: C09J 133/14 of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
• CPC Class Codes: C09J 4/06 Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00
• CPC Class Codes: C09K 2003/1065 Anaerobically hardenable materials
• CPC Class Codes: C09K 2200/0625 Polyacrylic esters or derivatives thereof
• CPC Class Codes: C09K 3/1006 characterised by the chemical nature of one of its constituents

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.

Claims

1. An anaerobic curable composition comprising;

(a) a (meth)acrylate component;

(b) an anaerobic cure system; and

(c) a compound within structure I

2. The composition of claim 1 wherein R₁ in the compound of (c) is a unit selected from C₂H₂, C₃H₄, C₄H₄, or C₄H₆.

3. The composition of claim 1 wherein the compound of (c) is the reaction product of a vinyl ether compound and a dicarboxylic acid.

4. The composition of claim 3 wherein the dicarboxylic acid is maleic acid.

5. The composition of claim 1 wherein the (meth)acrylate component is represented by:

H₂C═

CGCO₂R¹, 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;

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

8. The composition of claim 3 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.

7. A composition comprising the reaction product of:

(a) a (meth)acrylate component;

(b) an anaerobic cure system; and

(c) a compound within structure I

9. 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) a compound within structure I