Light-curing reactive adhesive film

Patent metadata

Field	Value
Publication number	US-12540258-B2
Application number	US-202217955755-A
Country	US
Kind code	B2
Filing date	Sep 29, 2022
Priority date	Sep 30, 2021
Publication date	Feb 3, 2026
Grant date	Feb 3, 2026

Abstract

The present invention relates to a light-curing, reactive, pressure-sensitive adhesive film of adhesive. With the film of adhesive of the invention, structural bond strengths can be achieved. The film of adhesive comprises (a) at least one reactive monomer or reactive resin, (b) an initiator, (c) a photoredox catalyst, (d) a polymer of monomers comprising N-vinyl compounds and (e) a film-forming polymer.

First claim

The invention claimed is:

1 . A single layer of a light-curing, reactive, pressure-sensitive adhesive film of adhesive, comprising
(a) at least one reactive monomer or reactive resin, (b) an initiator, (c) a photoredox catalyst, (d) a polymer obtained by radical polymerization of monomers containing carbon-carbon double bonds, wherein the monomers comprise N-vinyl compounds containing a nitrogen atom directly bonded to a vinyl group,
and
(e) a film-forming polymer.

2 . The single layer of a light-curing, reactive, pressure-sensitive adhesive film of adhesive according to claim 1 , wherein the reactive monomer or reactive resin (a) comprises at least one representative selected from acrylic esters, methacrylic esters, vinyl compounds, oligomeric compounds having carbon-carbon double bonds, polymeric compounds having carbon-carbon double bonds, and crosslinking reactive monomers.

3 . The single layer of a light-curing, reactive, pressure-sensitive adhesive film of adhesive according to claim 1 , wherein the photoredox catalyst (c) comprises
ruthenium as central atom and bipyridine or substituted bipyridine as ligand, or iridium as central atom and phenylpyridine or a substituted phenylpyridine as ligand.

4 . The single layer of a light-curing, reactive, pressure-sensitive adhesive film of adhesive according to claim 1 , wherein the photoredox catalyst (c) comprises [tris(2,2′-bipyridyl)ruthenium(II)] 2+ , tris[2-(2,4-difluorophenyl)pyridine]iridium(III) or tris(2-phenylpyridinato)iridium(III).

5 . The single layer of a light-curing, reactive, pressure-sensitive adhesive film of adhesive according to claim 1 , wherein the N-vinyl compounds of the polymer (d) are compounds corresponding to the formula (II) or comprise a structural unit of the formula (II),

where
A is an organic radical R or H,
B is an organic radical R or H or OR or OH or NR 2 or NHR or NH 2 ,
R independently and at each occurrence is a substituted or unsubstituted branched, cyclic or linear C 1-20 alkyl radical or C 2-20 alkenyl radical; or is a substituted or unsubstituted aryl or heteroaryl,
optionally the organic radical A and the organic radical B form a ring.

6 . The single layer of a light-curing, reactive, pressure-sensitive adhesive film of adhesive according to claim 1 , wherein the N-vinyl compounds of the polymer (d) comprise N-vinylcaprolactam or N-vinylpyrrolidone or 5-methyl-3-vinyl-2-oxazolidinone.

7 . The single layer of a light-curing, reactive, pressure-sensitive adhesive film of adhesive according to claim 1 , wherein the film-forming polymer (e) comprises a thermoplastic polymer, an elastomer and/or a thermoplastic elastomer.

8 . The single layer of a light-curing, reactive, pressure-sensitive adhesive film of adhesive according to claim 7 , wherein the film-forming polymer (e) comprises a thermoplastic polyurethane.

9 . The single layer of a light-curing, reactive, pressure-sensitive adhesive film of adhesive according to claim 1 , comprising
(a) 10 to 80 wt % of the at least one reactive monomer or reactive resin, (b) 0.1 to 10.0 wt % of the initiator, (c) up to 1.0 wt % of the photoredox catalyst, (d) 1.0 to 50.0 wt % of the polymer, (e) 10 to 90 wt % of the film-forming polymer.

10 . The single layer of a light-curing, reactive, pressure-sensitive adhesive film of adhesive according to claim 9 , comprising
(a) 20 to 60 wt % of the at least one reactive monomer or reactive resin, (b) 0.2 to 4.0 wt % of the initiator, (c) up to 0.5 wt % of the photoredox catalyst, (d) 5.0 to 30.0 wt % of the polymer, (e) 20 to 60 wt % of the film-forming polymer.

11 . The single layer of a light-curing, reactive, pressure-sensitive adhesive film of adhesive according to claim 1 , further comprising films, foils, layers, carriers, films of adhesive, films of pressure-sensitive adhesive, release papers and/or release liners.

12 . A reactive, pressure-sensitive adhesive tape comprising layers (A1), (A2) and (B), wherein the layer (B) is arranged flatly between the layers (A1) and (A2), wherein the layer (A1) is the single layer of a light-curing, reactive, pressure-sensitive adhesive film of adhesive according to claim 1 ; wherein the layer (B) is a film, a foil, or a carrier, and the layer (A2) is a reactive, pressure-sensitive adhesive film of adhesive.

13 . A method for producing bonds on material selected from plastic, metal, glass and ceramic, which comprises applying the single layer of a reactive, pressure-sensitive adhesive film of adhesive according to claim 1 to said material.

14 . A composite element comprising at least two bonding faces joined to one another by a cured product of the single layer of a reactive, pressure-sensitive adhesive film of adhesive according to claim 1 .

15 . The single layer of a light-curing, reactive, pressure-sensitive adhesive film of adhesive according to claim 2 , wherein the crosslinking reactive monomers is selected from diacrylates, dimethacrylates, triacrylates, trimethacrylates, acrylates of higher functionality, and methacrylates of higher functionality.

16 . The single layer of a light-curing, reactive, pressure-sensitive adhesive film of adhesive according to claim 2 , wherein the crosslinking reactive monomers is selected from 2-phenoxyethyl acrylate, 2-phenoxyethyl methacrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-hydroxy-3-phenoxypropyl methacrylate, 2-[2-(methacryloyloxy)ethoxycarbonyl]benzoic acid, 2-[[(phenylamino)carbonyl]oxy]ethyl methacrylate, 2-tert-butyl-6-[(3-tert-butyl-2-hydroxy-5-methylphenyl)methyl]-4-methyl¬phenyl prop-2-enoate, (5-ethyl-1,3-dioxan-5-yl)methyl acrylate, (2-oxo-1,3-dioxolan-4-yl)methyl methacrylate, di(ethylene glycol) 2-ethylhexyl ether acrylate, (2,2-dimethyl-1,3-dioxolan-4-yl)methyl prop-2-enoate, 2-succinic acid mono-[2-(acryloyloxy)ethyl ester], succinic acid mono-[2-(methacryloyloxy)ethyl ester], (2,2-pentamethylene-1,3-oxazolid-3-yl)ethyl methacrylate, 2-hydroxy-3-(prop-2-enoyloxy)propyl 2-methyl-2-propylhexanoate, 2-[[(butylamino)carbonyl]oxy]ethyl acrylate, stearyl acrylate, stearyl methacrylate, diurethane dimethacrylate (isomer mixture), bisphenol A glycerolate dimethacrylate (BIS-GMA), bisphenol A dimethacrylate (BIS-DMA), ethylene glycol diacrylate, ethylene glycol dimethacrylate, trimethyloylpropane propoxylate triacrylate, trimethyloylpropane triacrylate and di(trimethylolpropane) tetraacrylate.

17 . A method for producing bonds on material selected from plastic, metal, glass and ceramic, which comprises applying the reactive, pressure-sensitive adhesive tape according to claim 12 to said material.

18 . A composite element comprising at least two bonding faces joined to one another by a cured product of the reactive, pressure-sensitive adhesive tape according to claim 12 .

Assignees

• Tesa Se

Inventors

• Schümann Uwe
• Hannemann Frank
• Dietze Sebastian
• Czeski Tanita
• Rellmann-Sprink André

Classifications

• Y10T428/2891

  including addition polymer from alpha-beta unsaturated carboxylic acid [e.g., acrylic acid, methacrylic acid, etc.] Or derivative thereof · CPC title

• Y10T428/2809

  including irradiated or wave energy treated component · CPC title

• C09J2301/416

  use of irradiation · CPC title

• C09J2301/302

  the adhesive being pressure-sensitive, i.e. tacky at temperatures inferior to 30°C · CPC title

• C09J7/385 Primary

  Acrylic polymers · CPC title