Anaerobically curable (meth)acrylate compositions

Patent metadata

Field	Value
Publication number	US-2019031921-A1
Application number	US-201816148367-A
Country	US
Kind code	A1
Filing date	Oct 1, 2018
Priority date	Apr 1, 2016
Publication date	Jan 31, 2019
Grant date	—

Abstract

Anaerobically curable (meth)acrylate compositions, methods for their preparation, and uses thereof. The anaerobically curable compositions proved effective at bonding a wide variety of substrates, and the tensile strength performance of said compositions is excellent.

First claim

1 . An anaerobically curable one-part composition comprising:
(a) at least one (meth)acrylate component; (b) an anaerobic cure inducing component; and (c) a toughening agent selected from (i) a combination of a styrene butadiene block copolymer and methacrylate functionalized polybutadiene; or (ii) propoxylated bisphenol A fumarate polyester, or combinations of (i) and (ii).

2 . An anaerobically curable composition according to claim 1 wherein the methacrylate component is a (meth)acrylate monomer having the formula: H 2 C═CGCO2R 1 , wherein G may be hydrogen, halogen or alkyl groups having from 1 to about 4 carbon atoms, and R 1 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, polyurethane, carbonate, amine, amide, sulfur, sulfonate, and sulfone.

3 . An anaerobically curable composition according to claim 1 wherein the toughening agent is a combination of a styrene butadiene block copolymer and methacrylate functionalized polybutadiene and the styrene butadiene block copolymer is present in an amount of about 5 to about 30 wt %.

4 . An anaerobically curable composition according to claim 1 wherein the toughening agent is a combination of a styrene butadiene block copolymer and methacrylate functionalized polybutadiene and the methacrylate functionalized polybutadiene is present in an amount of about 5 to about 20 wt %.

5 . An anaerobically curable composition according to claim 1 wherein the toughening agent is a combination of a styrene butadiene block copolymer and methacrylate functionalized polybutadiene wherein the weight ratio of the methacrylate functionalized polybutadiene to the styrene butadiene block copolymer is from 1:5 to 5:1.

6 . An anaerobically curable composition according to claim 1 , wherein the toughening agent is a combination of a styrene butadiene block copolymer and methacrylate functionalized polybutadiene, and wherein the methacrylate functionalized polybutadiene is selected from the group consisting of methacrylate (vinyl) terminated polybutadiene and butadiene-acrylonitrile polymer.

7 . An anaerobically curable composition according to claim 6 , wherein the methacrylate functionalized polybutadiene is methacrylate (vinyl) terminated polybutadiene.

8 . An anaerobically curable composition according to claim 6 , wherein the methacrylate functionalized polybutadiene is butadiene-acrylonitrile polymer.

9 . An anaerobically curable composition according to claim 6 , wherein the methacrylate functionalized polybutadiene has a number average molecular weight of from about 3,000 to about 5,500.

10 . An anaerobically curable composition according to claim 9 wherein the methacrylate functionalized polybutadiene has a number average molecular weight of about 4,500.

11 . An anaerobically curable composition according to claim 9 wherein the methacrylate functionalized polybutadiene has a number average molecular weight of from about 3500 to about 4,000.

12 . An anaerobically curable composition according to claim 1 wherein the toughening agent comprises styrene butadiene block copolymer and wherein polystyrene represents about 35 wt % to about 45 wt % of the overall weight of the block copolymer, such as about 40 wt % of the overall weight of the block copolymer.

13 . An anaerobically curable composition according to claim 1 wherein the toughening agent is propoxylated bisphenol A fumarate polyester and is present in an amount of about 15 to about 45 wt %.

14 . An anaerobically curable composition according to claim 1 wherein the toughening agent is propoxylated bisphenol A fumarate polyester and has a number average molecular weight of from about 2,500 to about 3,000.

15 . An anaerobically curable composition according to 1 claim further comprising a transition metal.

16 . An anaerobically curable composition according to claim 15 wherein the transition metal is selected from copper, iron, vanadium, cobalt, chromium, silver and manganese, or combinations thereof.

17 . An anaerobically curable composition according to claim 15 wherein the transition metal is in salt form and is selected from the group consisting of: cobalt (II) naphthenate, copper carbonate, copper (II) acetylacetonate, silver nitrate, vanadium nitrate, vanadium (III) acetylacetonate and combinations thereof.

18 . An anaerobically curable composition according to claim 1 for bonding a first substrate to a second substrate.

19 . An anaerobically curable composition according to claim 18 , wherein the first substrate is a passive substrate.

20 . An anaerobically curable composition according to claim 19 , wherein the passive substrate is a plastic.

21 . An anaerobically curable composition according to claim 20 , wherein the plastic substrate is selected from: acrylonitrile butadiene styrene, polycarbonate, polycarbonate/acrylonitrile butadiene styrene, polyarylamides, polyamides, acrylic plastic, polyvinyl chloride, nylon 6′6, and polymethyl methacrylate.

22 . An anaerobically curable composition according to claim 18 , wherein the second substrate is metallic.

23 . An anaerobically curable composition according to claim 22 , wherein the second substrate is selected from the group consisting of steel, including mild steel and stainless steel, brass including clock brass, bronze, or zinc, aluminium, iron, copper, beryllium, cobalt, manganese, nickel, cadmium, gold, silver or alloys thereof.

24 . A method of bonding together two substrates comprising the steps of:
applying a (meth)acrylate composition according to claim 1 , to at least one of the substrates and mating together the substrates for a time sufficient to permit an adhesive bond to form from the (meth)acrylate composition between the mated substrates.

25 . An assembly comprising two substrates bonded together by the cure product of composition according to claim 1 .

26 . A method of anaerobically curing a (meth)acrylate composition comprising the steps of:
providing a one-part (meth)acrylate composition comprising: (a) a (meth)acrylate component; (b) a cure inducing component; and (c) a toughening agent selected from (i) a combination of a styrene butadiene block copolymer and methacrylate functionalized polybutadiene; or (ii) propoxylated bisphenol A fumarate polyester; and exposing the (meth)acrylate composition to an anaerobic environment for a time sufficient to cure the composition.

27 . A process for preparing a reaction product from a curable composition, comprising the steps of:
applying an activator composition to a desired substrate surface; applying to that surface an anaerobically curable one-part composition comprising: (a) a (meth)acrylate component; (b) a cure inducing component; and (c) a toughening agent selected from (i) a combination of a styrene butadiene block copolymer and methacrylate functionalized polybutadiene; or (ii) propoxylated bisphenol A fumarate polyester; mating a second surface to that substrate surface to form an assembly; and exposing the (meth)acrylate composition to an anaerobic environment for a time sufficient to cure the composition.

Assignees

• Henkel IP & Holding GmbH

Inventors

• Mullen David
• Sheerin Lynne
• Kneafsey Brendan

Classifications

• C09J11/04

  inorganic · CPC title

• B32B37/12

  characterised by using adhesives · CPC title

• C09J2433/00

  Presence of (meth)acrylic polymer · CPC title

• C09J2409/00

  Presence of diene rubber · CPC title

• C09J11/08

  Macromolecular additives · CPC title