Photo-curable adhesive composition, preparation and use thereof

Patent metadata

Field	Value
Publication number	US-10717907-B2
Application number	US-201715598864-A
Country	US
Kind code	B2
Filing date	May 18, 2017
Priority date	Nov 18, 2014
Publication date	Jul 21, 2020
Grant date	Jul 21, 2020

Abstract

The present invention provides a photo-curable adhesive composition for display panel assembly comprising a) at least one polyurethane acrylate having Tg value from −70 to 20° C.; b) at least one (meth)acrylate monomer; c) at least one chain transfer agent; d) at least two thixotropy agents, wherein first thixotropy agent is selected from the group consisting of hydrophobic fumed silica, hydrophilic fumed silica and mixtures thereof and second thixotropy agent is selected from the group consisting of modified urea, polyhydroxycarboxylic acid esters and mixtures thereof; e) at least one photoinitiator; f) at least one plasticizer; and g) at least one defoamer. The photo-curable adhesive composition according to the present invention can be used in bonding two transparent substrates together or in bonding one transparent substrate and one opaque substrate together. Furthermore, the composition according to the present invention can be used in a process of making an optical assembly.

First claim

What is claimed is:

1. A photo-curable adhesive composition comprising
a) at least one polyurethane acrylate having a Tg value from −70 to 20° C.;
b) at least one (meth)acrylate monomer;
c) at least one thiol chain transfer agent present in an amount of 0.1% by weight to 3% by weight of the total composition;
d) at least two thixotropy agents, wherein a first thixotropy agent is selected from the group consisting of hydrophobic fumed silica, hydrophilic fumed silica and mixtures thereof and is present in an amount of about 0.01% by weight to about 10% by weight of the total composition, and a second thixotropy agent is selected from the group consisting of modified urea, polyhydroxycarboxylic acid esters and mixtures thereof and is present in an amount of about 0.01% by weight to about 5% by weight of the total composition;
e) at least one photoinitiator;
f) at least one plasticizer; and
g) at least one defoamer selected from the group consisting of silicone defoamers, polyether defoamers and mineral oil defoamers and mixtures thereof.

2. The composition according to claim 1 , wherein said polyurethane acrylate is an aliphatic polyether urethane or acrylic ester.

3. The composition according to claim 1 , wherein said (meth)acrylate monomer is a mono-functional or di-functional (meth)acrylate monomer.

4. The composition according to claim 1 , wherein said thiol chain transfer agent is selected from the group consisting of n-octyl mercaptan, n-dodecyl mercaptan, tertiary-dodecyl mercaptan, methyl mercaptan, ethyl mercaptan, tertio-butyl mercaptan, benzyl mercaptan, tertio-nonyl mercaptan, thioglycolic, iso-octyl thioglycolate, 2-ethylhexyl thioglycolate, 1,8-dimercapto-3,5-dioxaoctane, dibenzylthithiocarbonate, β-mercaptopropionic, methyl 3-mercaptopropionate, 2-ethylhexyl-3-mercaptopropionate, n-octyl-3-mercaptopropioate, methoxybuthyl-3-mercaptopropionate, stearyl-3-mercaptopropionate, 8-dimercapto-3,6-dioxaoctane, trimethylolpropane tris-3-mercaptopropionate, tris [(3-mercaptopropionyloxy)-ethyl]-isocyanurate, pentaerythritol tetrakis-3-mercaptopropionate, tetraethyleneglycol bis(3-mercaptopropionate), dipentaerythritol hexa-3-mercaptopropionate and mixtures thereof.

5. The composition according to claim 1 , wherein said photoinitiator is selected from the group consisting of 1-hydroxy cyclohexyl phenyl ketone, 2-methyl-1-[4-(methylthio)phenyl]-2-morpholino propan-1-one, 2-benzyl-1-N,N-dimethylamino-1-(4-morpholinophenyl)-1-butanone, combination of 1-hydroxy cyclohexyl phenyl ketone and benzophenone, 2,2-dimethoxy-2-phenyl acetophenone, combination of bis(2,6-dimethoxybenzoyl-2,4,6-trimethylpentyl) phosphine oxide and 2-hydroxyl-2-methyl-1-phenyl-propan-1-one, bis(2,4,6-trimethyl benzoyl) phenyl phosphine oxide, 2-hydroxy-2-methyl-1-phenyl-1-propane, combination of 2,4,6-trimethylbenzoyl diphenyl phosphine oxide and 2-hydroxy-2-methyl-l-phenyl-propan-1-one, 2,4,6-trimethylbenzoyldiphenylphosphine oxide and mixtures thereof.

6. The composition according to claim 1 , wherein said plasticizer is selected from the group consisting of polyisoprene resin, polybutadiene resin, hydrogenated polybutadiene, xylene polymer, hydroxyl-terminated polybutadiene and/or hydroxyl-terminated polyolefin, triethylene glycol bis(2-ethylhexanoate), dibutoxyethoxyethyl adipate, and mixtures thereof.

7. The composition according to claim 1 , comprises said polyurethane acrylate from 10% to 90% by weight of the total weight of the composition.

8. The composition according to claim 1 , comprises said (meth)acrylate monomer from 5% to 40% by weight of the total weight of the composition.

9. The composition according to claim 1 , comprises said photo-initiator from 0.02% to 5% by weight of the total weight of the composition.

10. The composition according to claim 1 , comprises said plasticizer from 0.1% to 80% by weight of the total weight of the composition.

11. The composition according to claim 1 , comprises said defoamer from 0.01% to 1.0% by weight of the total weight of the composition.

12. A process to prepare a composition according to claim 1 , comprising steps of:
(i) preparing first pre-mix comprising a (meth)acrylate monomer, a photoinitiator, a chain transfer agent, first thixotropy agent, second thixotropy agent and a defoamer, and grinding the pre-mixture to particles having average particle diameter between 5 to 10 μm;
(ii) preparing second pre-mix comprising a polyurethane acrylate and plasticizer;
(iii) combining first pre-mix and second pre-mix and mixing with shear blade.

13. A process comprising steps of bonding two transparent substrates together or bonding one transparent substrate and one opaque substrate together using the composition according to claim 1 .

14. The process according to claim 13 , wherein the said transparent substrate is glass or plastic.

15. A process of making an optical assembly comprising steps of bonding two transparent substrates together or bonding one transparent substrate and one opaque substrate together using the composition according to claim 1 .

16. The composition according to claim 1 , wherein said (meth)acrylate monomer is selected from the group consisting of methyl (meth)acrylate, ethyl (meth)acrylate, butyl (meth)acrylate, 2-(2-ethoxyethoxy) ethyl acrylate, tetrahydrofurfuryl (meth)acrylate, lauryl actylate, isooctyl acrylate, n-octyl acrylate, isodecyl acrylate, n-decyl acrylate, 2-phenoxythyl acrylate, isobornyl acrylate, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2(or 4)-hydroxybutyl (meth)acrylate, caprolactone acrylate, morpholine (meth)acrylate, morpholine, 4-acryloyl-, hexanediol di(meth)acrylate, ethyleneglycol di(meth)acrylate and mixtures thereof.

Assignees

• Henkel Ag & Co Kgaa

Inventors

• Wang Hongyu
• Chen Chunfu
• Lu Daoqiang
• Li Minrui
• Yuan Yinxiao

Classifications

• C08F290/067

  Polyurethanes; Polyureas · CPC title

• B32B2457/20

  Displays, e.g. liquid crystal displays, plasma displays · CPC title

• B32B2307/41

  Opaque · CPC title

• C09J11/06

  organic · CPC title

• B32B17/10706

  being photo-polymerized · CPC title