Anaerobically curable (meth)acrylate compositions

Patent metadata

Field	Value
Publication number	US-11111416-B2
Application number	US-201816148367-A
Country	US
Kind code	B2
Filing date	Oct 1, 2018
Priority date	Apr 1, 2016
Publication date	Sep 7, 2021
Grant date	Sep 7, 2021

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

The invention claimed is:

1. An anaerobically curable composition comprising:
(a) at least one (meth)acrylate component;
(b) an anaerobic cure inducing component; and
(c) a toughening agent selected from the group consisting of: (i) a combination of a styrene butadiene block copolymer and methacrylate functionalised polybutadiene; and (ii) a combination of a styrene butadiene block copolymer, methacrylate functionalised polybutadiene and propoxylated bisphenol A fumarate polyester; wherein the composition will not cure until exposed to an anaerobic environment and wherein the toughening agent is a combination of a styrene butadiene block copolymer and methacrylate functionalised polybutadiene and the methacrylate functionalised polybutadiene is present in an amount of about 5 to about 20 wt %.

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 functionalised 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 functionalised polybutadiene, and wherein the weight ratio of the methacrylate functionalised polybutadiene to the styrene butadiene block copolymer is from 1:5 to 5:1.

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

6. An anaerobically curable composition according to claim 5 , wherein the methacrylate functionalised polybutadiene is methacrylate (vinyl) terminated polybutadiene.

7. An anaerobically curable composition according to claim 5 , wherein the methacrylate functionalised polybutadiene is butadiene-acrylonitrile polymer.

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

9. An anaerobically curable composition according to claim 8 wherein the methacrylate functionalised polybutadiene has a number average molecular weight of about 4,500.

10. An anaerobically curable composition according to claim 8 wherein the methacrylate functionalised polybutadiene has a number average molecular weight of from about 3500 to about 4,000.

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

12. An anaerobically curable composition according to claim 11 , wherein the first substrate is a passive substrate.

13. An anaerobically curable composition according to claim 12 , wherein the passive substrate is a plastic.

14. An anaerobically curable composition according to claim 13 , wherein the plastic substrate is selected from the group consisting of acrylonitrile butadiene styrene, polycarbonate, polycarbonate/acrylonitrile butadiene styrene, polyarylamides, polyamides, acrylic plastic, polyvinyl chloride, nylon 6′6, and polymethyl methacrylate.

15. An anaerobically curable composition according to claim 11 , wherein the second substrate is metallic.

16. An anaerobically curable composition according to claim 15 , 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.

17. 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.

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

19. An anaerobically curable composition comprising:
(a) at least one (meth)acrylate component;
(b) an anaerobic cure inducing component; and
(c) a toughening agent selected from the group consisting of (i) a combination of a styrene butadiene block copolymer and methacrylate functionalised polybutadiene; and (ii) a combination of a styrene butadiene block copolymer, methacrylate functionalised polybutadiene and propoxylated bisphenol A fumarate polyester; wherein the composition will not cure until exposed to an anaerobic environment, and 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.

20. An anaerobically curable composition, comprising:
(a) at least one (meth)acrylate component;
(b) an anaerobic cure inducing component; and
(c) a toughening agent selected from the group consisting of (i) a combination of a styrene butadiene block copolymer and methacrylate functionalised polybutadiene; and (ii) a combination of a styrene butadiene block copolymer, methacrylate functionalised polybutadiene and propoxylated bisphenol A fumarate polyester; wherein the composition will not cure until exposed to an anaerobic environment, and wherein the toughening agent comprises propoxylated bisphenol A fumarate polyester present in an amount of about 15 to about 45 wt %.

21. An anaerobically curable composition comprising:
(a) at least one (meth)acrylate component;
(b) an anaerobic cure inducing component; and
(c) a toughening agent selected from the group consisting of (i) a combination of a styrene butadiene block copolymer and methacrylate functionalised polybutadiene; and (ii) a combination of a styrene butadiene block copolymer, methacrylate functionalised polybutadiene and propoxylated bisphenol A fumarate polyester; wherein the composition will not cure until exposed to an anaerobic environment, and wherein the toughening agent comprises propoxylated bisphenol A fumarate polyester having a number average molecular weight of from about 2,500 to about 3,000.

22. An anaerobically curable composition, comprising:
(a) at least one (meth)acrylate component;
(b) an anaerobic cure inducing component; and
(c) a toughening agent selected from the group consisting of (i) a combination of a styrene butadiene block copolymer and methacrylate functionalised polybutadiene; and (ii) a combination of a styrene butadiene block copolymer, methacrylate functionalised polybutadiene and propoxylated bisphenol A fumarate polyester; wherein the composition will not cure until exposed

Assignees

• Henkel IP & Holding GmbH

Inventors

• Mullen David
• Sheerin Lynne
• Kneafsey Brendan

Classifications

• C09J133/12

  Homopolymers or copolymers of methyl methacrylate · CPC title

• C09J109/00

  Adhesives based on homopolymers or copolymers of conjugated diene hydrocarbons · CPC title

• C08K5/14

  Peroxides · CPC title

• C08L33/14

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

• B05D7/14

  to metal, e.g. car bodies (involving a chemical reaction between the metal and the coating C23) · CPC title