Photoinitiators that are polymeric or polymerizable for use in UV curable pressure sensitive adhesives

Patent metadata

Field	Value
Publication number	US-10526426-B2
Application number	US-201715702199-A
Country	US
Kind code	B2
Filing date	Sep 12, 2017
Priority date	Mar 20, 2015
Publication date	Jan 7, 2020
Grant date	Jan 7, 2020

Abstract

Disclosed are photoinitiators that are ultra violet (UV) reactive. The photoinitiators can be polymerized into polymeric backbones for use in UV curable hot melt pressure sensitive adhesives. The preferred polymeric backbones are acrylic-based polymers. The photoinitiators are very UVC sensitive and have excellent hot melt viscosity stability that is many fold higher than existing photoinitiators. The subject photoinitiators feature aryl ketones linked through an ether linkage to a variety of connector sequences that allow for polymerization of the photoinitiators.

First claim

We claim:

1. A photoinitiator having a structure as defined in formula I below:

wherein:
Ar is selected from the group consisting of:

wherein:
R 2 , R 3 and R 4 are independently: a linear alkyl group; a branched alkyl group; a cycloalkyl group; an alkylenoxy group; an alkenyl group; an aryl group; or an alkyl group containing a heteroatom; a carbonyl group; H; F; Cl; Br; I; OR; NR 2 ; or SR wherein R in OR, NR 2 , or SR is one of an alkyl, an aryl, or a heteroaryl group;
X 1 is optional, if present it is one of: CH 2 ; a linear alkyl group; a branched alkyl group; a cycloalkyl group; a linear alkyl group containing at least one of heteroatoms, a carbonyl, an ester, a carbonate, and mixtures thereof at any position; a branched alkyl group containing at least one of heteroatoms, a carbonyl, an ester, a carbonate, and mixtures thereof at any position; or a cycloalkyl group containing at least one of heteroatoms, a carbonyl, an ester, a carbonate, and mixtures thereof at any position;
X 2 is one of: a linear alkyl group; a branched alkyl group; a cycloalkyl group; a linear alkyl group containing at least one of heteroatoms, a carbonyl, an ester, a carbonate, and mixtures thereof at any position; a branched alkyl group containing at least one of heteroatoms, a carbonyl, an ester, a carbonate, and mixtures thereof at any position; or a cycloalkyl group containing at least one of heteroatoms, a carbonyl, an ester, a carbonate, and mixtures thereof at any position; and
R is H or CH 3 .

2. The photoinitiator as recited in claim 1 , wherein the photoinitiator is selected from the group consisting of:

and
mixtures thereof.

3. An ultra violet light curable polymer comprising:
an acrylic polymer that is a reaction product of a plurality of one or more acrylic monomers and one or more photoinitiators according to claim 1 , wherein said acrylic polymer is crosslinkable through said photoinitiator groups upon exposure to ultra violet light.

4. The ultra violet light curable polymer according to claim 3 wherein the photoinitiator is present in an amount of from 0.1 to 10 mole percent based on the total number of moles of acrylate monomers used for polymerization to obtain the acrylic polymer.

5. The ultra violet light curable polymer according to claim 3 wherein the photoinitiator is selected from the group consisting of:

and
mixtures thereof.

6. The ultra violet light curable polymer according to claim 3 wherein the acrylic monomers are selected from the group consisting of: acrylic acid, methacrylates, methyl methacrylates, ethyl acrylates, 2-chloroethyl vinyl ethers, 2 ethylhexyl acrylate, acetoacetoxyethyl methacrylate (AAEM), hydroxyethyl methacrylate, butyl acrylate, butyl methacrylate, trimethylolpropane triacrylate (TMPTA), and mixtures thereof.

7. A hot melt pressure sensitive adhesive that is ultra violet light curable and comprises:
an acrylic polymer that is a reaction product of a plurality of one or more acrylic monomers and one or more photoinitiators according to claim 1 , wherein said acrylic polymer is crosslinkable through said photoinitiator groups upon exposure to ultra violet light, and optionally a tackifier.

8. The hot melt pressure sensitive adhesive that is ultra violet light curable according to claim 7 wherein at least one tackifier is present and said at least one tackifier comprises a rosin ester, a terpene phenol, an ester of a hydrogenated rosin, a synthetic hydrocarbon, and mixtures thereof.

Assignees

• Henkel IP & Holding GmbH

Inventors

• Sridhar Laxmisha
• Silverberg Eric N
• Burdzy Sean M
• Messana Andrew D
• Woods John G
• Stevens Bruce

Classifications

• C07C323/12

  the carbon skeleton being acyclic and saturated · CPC title

• C09J4/00

  Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond {; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16} · CPC title

• C08F2/50

  with sensitising agents · CPC title

• C09J133/14

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

• C09J4/06

  {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 title