One-part anaerobically curable compositions

Patent metadata

Field	Value
Publication number	US-12241003-B2
Application number	US-202117468500-A
Country	US
Kind code	B2
Filing date	Sep 7, 2021
Priority date	Mar 7, 2019
Publication date	Mar 4, 2025
Grant date	Mar 4, 2025

Abstract

Disclosed herein are anaerobically curable compositions comprising one or more polymerizable (meth)acrylate ester monomers, a redox-active metal catalyst, saccharin or a saccharin derivative, a peroxide, and a benzoyl functionalized compound, wherein the composition does not gel after about 24 hours of storage at room temperature and methods of adhering two substrates using the anaerobically curable compositions.

First claim

The invention claimed is:

1. An anaerobically curable composition comprising:
one or more polymerizable (meth) acrylate ester monomers,
a redox-active metal catalyst,
saccharin or a saccharin derivative,
a peroxide, and
a benzoyl functionalized compound,

wherein the benzoyl functionalized compound and the redox-active metal catalyst are present in the composition in a ratio of at least 3:1,
wherein the composition does not gel after about 24 hours of storage at room temperature.

2. The anaerobically curable composition of claim 1 , wherein the composition further comprises one or more oligomeric polymerizable (meth) acrylate monomers.

3. The anaerobically curable composition of claim 1 , wherein the composition further comprises an amine.

4. The anaerobically curable composition of claim 3 , wherein the amine is a secondary aromatic amine.

5. The anaerobically curable composition of claim 1 , wherein the composition further comprises a free radical stabilizer, acrylic acid, silica or inorganic fillers, chelators, or a combination thereof.

6. The anaerobically curable composition of claim 1 , wherein the benzoyl functionalized compound is a photoinitiator.

7. The anaerobically curable composition of claim 6 , wherein the photoinitiator is selected from the group consisting of: 1-hydroxycyclohexyl phenyl ketone; 2-methyl-1-[4-(methylthio) phenyl]-2-morpholino-propan-1-one; 2-benzyl-2-N, N-dimethylamino-1-(4-morpholinophenyl)-1-butanone; a combination of 1-hydroxy cyclohexyl phenyl ketone and benzophenone; 2,2-dimethoxy-2-phenyl acetophenone; a combination of bis (2,6-dimethoxybenzoyl-2,4,4-trimethyl pentyl phosphine oxide and 2-hydroxy-2-methyl-1-phenyl-propan-1-one; 2-hydroxy-2-methyl-1-phenyl-1-propane; a combination of 2,4,6-trimethylbenzoyldiphenyl-phosphine oxide and 2-hydroxy 2-methyl-1-phenyl-propan-1-one;

and, any combination thereof.

8. The anaerobically curable composition of claim 1 , wherein the composition is capable of cure at less than about 85° C.

9. The anaerobically curable composition of claim 1 , wherein the redox-active metal catalyst is iron (II) naphthenate, EDTA.2Na. Cu (II), ff copper naphthenate, vanadium acetylacetonate, vanadyl acetylacetonate, iron (II) acetate, or a combination thereof.

10. The anaerobically curable composition of claim 1 , wherein the peroxide is present in an amount from about 0.5 to about 10 wt. % based on the total weight of the composition.

11. The anaerobically curable composition of claim 1 , wherein the benzoyl functionalized compound is present in an amount from about 0.1 to about 5 wt. % based on the total weight of the composition.

12. The anaerobically curable composition of claim 1 , wherein the redox-active metal catalyst in an amount from about 0.0001 to about 2 wt. % based on the total weight of the composition.

13. A method of adhering two substrates comprising:
obtaining two substrates, each having surfaces;
applying an anaerobically curable composition of claim 1 to one or both substrates;
combining the two substrates;
thermally curing the anaerobically curable composition at about 60° C. to about 80° C. for about 20 min,

wherein one substrate of the two substrates is a plastic substrate,
wherein the surfaces of the substrates are not activated or otherwise primed.

14. The method of claim 13 , wherein the anaerobically curable composition comprises a benzoyl functionalized compound that is a photoinitiator.

15. An assembly comprising two substrates bonded together by a cure product of an anaerobically curable composition according to Claim 1 .

16. A method of adhering two substrates comprising:
obtaining two substrates, each having surfaces;
applying to one or both of the substrates an anaerobically curable composition comprising:
one or more polymerizable (meth) acrylate ester monomers,
a redox-active metal catalyst,
saccharin or a saccharin derivative,
peroxide, and
a benzoyl functionalized compound,

wherein the benzoyl functionalized compound and the redox-active metal catalyst are present in the composition in a ratio of at least 3:1;
combining the two substrates;
thermally curing the anaerobically curable composition at less than about 80° C. for about 20 min,

wherein one substrate of the two substrates is a plastic substrate,
wherein the surfaces of the substrates are not activated or otherwise primed.

17. The method of claim 16 , wherein the benzoyl functionalized compound is a photoinitiator.

18. The method of claim 17 , wherein the photoinitiator is selected from the group consisting of: 1-hydroxycyclohexyl phenyl ketone; 2-methyl-1-[4-(methylthio) phenyl]-2-morpholino-propan-1-one; 2-benzyl-2-N,N-dimethylamino-1-(4-morpholinophenyl)-1-butanone; a combination of 1-hydroxy cyclohexyl phenyl ketone and benzophenone; 2,2-dimethoxy-2-phenyl acetophenone; a combination of bis (2,6-dimethoxybenzoyl-2,4,4-trimethyl pentyl phosphine oxide and 2-hydroxy-2-methyl-1-phenyl-propan-1-one; 2-hydroxy-2-methyl-1-phenyl-1-propane; a combination of 2,4,6-trimethylbenzoyldiphenyl-phosphine oxide and 2-hydroxy 2-methyl-1-phenyl-propan-1-one;

and, any combination thereof.

Assignees

• Henkel Ag & Co Kgaa

Inventors

• Fearon Stephen
• Sweeney Nigel
• Coughlan Gerry
• Condron David
• Kneafsey Brendan

Classifications

• C09J175/16

  having terminal carbon-to-carbon unsaturated bonds · CPC title

• C09J133/14

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

• C08G2170/00

  Compositions for adhesives · CPC title

• C08G18/7621

  being toluene diisocyanate including isomer mixtures · CPC title

• C08G18/672

  Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen · CPC title