(Meth)acrylate urethane (urea) phosphonates as adhesion promoters

Patent metadata

Field	Value
Publication number	US-11912801-B2
Application number	US-201917271134-A
Country	US
Kind code	B2
Filing date	Aug 21, 2019
Priority date	Aug 30, 2018
Publication date	Feb 27, 2024
Grant date	Feb 27, 2024

Abstract

A curable composition is provided comprising a urethane (meth)acrylate oligomer, a urethane (urea) phosphonate ad-hesion promoter, optionally reactive diluents, and an initiator. The use of the urethane (urea) phosphonate adhesion promotor provides better ageing stability and adhesion, as measured by T-peel adhesion test, than the use of other conventional adhesion promotors.

First claim

What is claimed is:

1. A curable composition comprising:
a multifunctional urethane (meth)acrylate oligomer, wherein the multifunctional urethane (meth)acrylate oligomer is of the general formula:

wherein
Z is an ethylenically unsaturated, free radical polymerizable group,
R ISO is the residue of a polyisocyanate having at least two of its—NCO groups reacted to form a urethane bonding Z to R OH , subscript a is 0 or 1, b is 2-6, and
R OH is the residue of a polyol having at least a+b hydroxyl groups and a number average molecular weight between 90 and 10,000, the residue formed by removal of hydrogen from the hydroxyl groups;
optionally a reactive diluent;
an initiator;
a multifunctional (meth)acrylate crosslinker containing no urethane functional groups; and
an adhesion promoter of the formula:

wherein
R 1 is H or C 1 -C 4 alkyl R 2 and R 3 are each independently a (hetero)hydrocarbyl group; R 5 is H or C 1 -C 4 alkyl; X 1 is -O- or -NR 4 -, where R 4 is H or C 1 -C 4 alkyl, subscript x is 1 or 2; and subscript y is 1 or 2;
wherein the curable composition comprises 0.1 pbw to about 10 pbw of the multifunctional (meth)acrylate crosslinker based on 100 pbw of the total polymerizable components of the composition.

2. The curable composition of claim 1 further comprising a reactive diluent.

3. The curable composition of claim 1 comprising:
a) 10 pbw to about 85 pbw urethane (meth)acrylate oligomer;
b) 1 pbw to about 50 pbw reactive diluent;
c) 1-40 pbw of said adhesion promotor,
wherein the sum of the polymerizable component is 100 pbw.

4. The curable composition of claim 3 comprising 10 to 40 pbw reactive diluent.

5. The curable composition of claim 3 , wherein the initiator comprises a photoinitiator and the curable composition comprises 0.1 pbw to about 8 pbw of the photoinitiator.

6. The curable composition of claim 5 wherein the photoinitiator has an extinction coefficient of from about 10 to about 2000 L/mol. cm at a wavelength from about 400 nm to about 500 nm.

7. The curable composition of claim 5 , wherein the photoinitiator comprises

8. The curable composition of claim 5 further comprising a photosensitizer.

9. The curable composition of claim 8 wherein the photosensitizer comprises camphorquinone.

10. The curable composition of claim 1 , wherein the reactive diluent is a low viscosity (meth)acrylate monomer.

11. The curable composition of claim 1 , wherein the curable composition further comprises about 0.5 to about 10 pbw corrosion inhibitor.

12. The curable composition of claim 1 , further comprising a photobleachable dye as curing indicator.

13. The curable composition of claim 1 , further comprising a radical stabilizer.

14. The curable composition of claim 1 , further comprising a rheology modifier.

Assignees

• 3M Innovative Properties Company

Inventors

• Lin Ying
• Ye Sheng
• Klun Thomas P
• Colak Atan Semra
• Rasmussen Jerald K

Classifications

• C08F222/1065 Primary

  of alcohol terminated (poly)urethanes, e.g. urethane(meth)acrylates · CPC title

• C08F2/50

  with sensitising agents · CPC title

• C08K5/08

  Quinones · CPC title

• C08K5/5313

  Phosphinic compounds, e.g. R2=P(:O)OR' · CPC title

• C08K5/5393

  Phosphonous compounds, e.g. R—P(OR')2 · CPC title