Curable composition and use thereof

Patent metadata

Field	Value
Publication number	US-2024124621-A1
Application number	US-202318515628-A
Country	US
Kind code	A1
Filing date	Nov 21, 2023
Priority date	May 21, 2021
Publication date	Apr 18, 2024
Grant date	—

Abstract

The present invention provides a curable composition comprising (A) at least one (meth)acrylate; (B) at least one diaryliodonium salt; and (C) at least one latent amine catalyst, which can thermally be curable at a temperature of lower than 100° C. and can be also thermally curable and radiation curable. The present curable composition exhibits favorable adhesion strength on various substrates when cured.

First claim

What is claimed is:

1 . A curable composition comprising:
(A) at least one (meth)acrylate; (B) at least one diaryliodonium salt; and (C) at least one latent amine catalyst.

2 . The curable composition according to claim 1 , wherein the component (A) is selected from monofunctional (meth)acrylate monomers, polyfunctional (meth)acrylate monomers and oligomers thereof.

3 . The curable composition according to claim 2 , wherein the monofunctional (meth)acrylate monomer is selected from methyl (meth)acrylate, (meth)acrylic acid, ethyl (meth)acrylate, n-propyl (meth)acrylate, isopropyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, tert-butyl (meth)acrylate, n-pentyl (meth)acrylate, n-hexyl (meth) acrylate, cyclohexyl (meth)acrylate, n-heptyl (meth)acrylate, n-octyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, nonyl (meth)acrylate, decyl (meth)acrylate, dodecyl (meth) acrylate, tricyclodecanyl (meth)acrylate, dicyclopentenyl (meth)acrylate, phenyl (meth)acrylate, tolyl (meth)acrylate, benzyl (meth)acrylate, 2-methoxyethyl (meth)acrylate, 3-methoxybutyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, stearyl (meth)acrylate, glycidyl (meth)acrylate, 2-phenoxyethyh acrylate, 2-aminoethyl (meth)acrylate, dimethylaminoethyl (meth)acrylate, diethylaminoethyl (meth)acrylate, and combinations thereof.

4 . The curable composition according to claim 2 , wherein the polyfunctional (meth)acrylate monomer is selected from ethoxylated trimethylolpropane triacrylate, trimethylol propane tri(meth)acrylate, dipentaerythritol pentaacrylate, pentaerythritol triacrylate, 1,6-hexanedioldiacrylate, neopentyl glycol diacrylate, pentaerythritol tetraacrylate, 1,4-butanediol diacrylate, trimethylolpropane tri(meth)acrylate, tri(propylene glycol) diacrylate, neopentyl glycol propoxylate diacrylate, diethylene glycol dimethacrylate, bisphenol A diglycidyl ether di(meth)acrylate, dicyclopentadiene dimethanol di(meth)acrylate, tricyclodecanedimethanol diacrylate, and combinations thereof.

5 . The curable composition according to claim 1 , wherein the component (B) is selected from diphenyl iodonium phosphate, diphenyl iodonium borate, and the combination thereof; preferably selected from (4-methylphenyl)-[4-(2-methylpropyl)phenyl]iodonium hexafluorophosphate, (4-methylphenyl)-phenyliodonium hexafluorophosphate, bis(4-tert-butylphenyl)iodonium hexafluorophosphate, bis(4-methylphenyl)iodonium hexafluorophosphate, (4-ethylphenyl)-[4-(2-methylpropyl)phenyl]iodoniumhexafluorophosphate, bis(t-butylphenyl)iodonium hexafluorophosphate, bis(3,4-dimethylphenyl)iodonium hexafluorophosphate, (4-isopropylphenyl)(p-tolyl)iodonium tetrakis(perfluorophenyl)borate, (4-methylphenyl)-(2-propan-2-ylphenyl)iodonium tetrakis(2,3,4,5,6-pentafluorophenyl)boranuide, bis(2-methylphenyl)iodonium tetrakis(2,3,4,5,6-pentafluorophenyl)boranuide, (4-methylphenyl)-[4-(2-methylpropyl)phenyl]iodonium tetrakis(2,3,4,5,6-pentafluorophenyl)boranuide, bis(4-dodecylphenyl)iodonium tetrakis(2,3,4,5,6-pentafluorophenyl)boranuide, bis(2-dodecylphenyl)iodonium tetrakis(2,3,4,5,6-pentafluorophenyl)boranuide, (2-methylphenyl)-(2-propan-2-ylphenyl)iodonium tetrakis(2,3,4,5,6-pentafluorophenyl)boranuide, bis(2-tert-butylphenyl)iodonium tetrakis(2,3,4,5,6-pentafluorophenyl)boranuide, 1,4-di(3-phenylpropyl)-2,3-diperfluorophenyl-1,4-diiodobutadiene, butyl(triphenyl)boranuide (4-cyclohexylphenyl)-(4-methylphenyl)iodonium, (4-hexylphenyl)-phenyliodonium tetraphenylboranuide, (4-cyclohexylphenyl)-phenyliodonium tetraphenylboranuide, and combinations thereof.

6 . The curable composition according to claim 1 , wherein the component (C) is selected from amine adduct latent amine catalyst, preferably obtained by the reaction products of an amine compound with an epoxy compound, an isocyanate compound and/or a urea compound; core-shell type latent amine catalyst; master batch type latent amine catalyst; and combinations thereof.

7 . The curable composition according to claim 1 , wherein the composition further comprises (D) at least one additive selected from curing reaction inhibitors, pigments, dyes, fluorescent dyes, heat resistant additives, flame retardants, plasticizers, adhesion-imparting agents, fillers, and combinations thereof.

8 . The curable composition according to claim 1 , wherein the composition is thermally curable.

9 . The curable composition according to claim 1 , wherein the composition further comprises (E) at least one photo radical polymerization initiator.

10 . The curable composition according to claim 9 , wherein the photo radical polymerization initiator is α-cleavage photo radical polymerization initiator, hydrogen abstracting photo radical polymerization initiator and combinations thereof, preferably selected from benzyl dimethyl ketal, benzoin ethers, hydroxy alkyl phenyl ketones, benzoyl cyclohexanol, dialkoxy acetophenones, 1-hydroxycyclohexyl phenyl ketone, trimethylbenzoyl phosphine oxides, methyl thio phenyl morpholino ketones and morpholino phenyl amino ketones, benzophenones, thioxanthones, benzyls, camphorquinones, ketocoumarins; and combinations thereof.

11 . The curable composition according to claim 9 , wherein the composition is thermally curable and radiation curable.

12 . The curable composition according to claim 1 , wherein the component (A) is present in an amount of from 50% to 95% by weight based on the total weight of the composition.

13 . The curable composition according to claim 1 , wherein the component (B) is present in an amount of from larger than 0% to less than 3% by weight based on the total weight of the composition.

14 . The curable composition according to claim 1 , wherein the component (C) is present in an amount of from 3% to 47% by weight based on the total weight of the composition.

15 . The curable composition according to claim 1 , wherein the component (D) is present in an amount of from larger than 0% to 10% by weight based on the total weight of the composition.

16 . The curable composition according to claim 1 , wherein the component (E) is present in an amount of from 0% to 10% by weight based on the total weight of the composition.

17 . Cured product of a curable composition according to claim 1 .

18 . An article comprising:
a first substrate, a cured product according to claim 17 , and a second substrate bonded to the first substrate through the cured product.

19 . An electronic device comprising the article according to claim 18 .

Assignees

• Henkel Ag & Co Kgaa

Inventors

• Xun Weiwei
• Wu Qili
• Zhao Bin
• Ye Lvyuan

Classifications

• C08F20/06 Primary

  Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof · CPC title

• C08F2/44

  Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers · CPC title

• C08F4/027

  Polymers · CPC title

• C08F22/1006 Primary

  of polyhydric alcohols or polyhydric phenols, e.g. ethylene glycol dimethacrylate · CPC title

• C08K5/5337

  containing also halogens · CPC title