Radical curable adhesive composition, and polarizing plate and optical member comprising same

Patent metadata

Field	Value
Publication number	US-9790403-B2
Application number	US-201414902535-A
Country	US
Kind code	B2
Filing date	Sep 29, 2014
Priority date	Sep 30, 2013
Publication date	Oct 17, 2017
Grant date	Oct 17, 2017

Abstract

The present invention relates to a radical-curable adhesive composition including a (A) radical-polymerizable compound having at least one hydrophilic functional group in the molecule; a (B) phosphate-based compound having three (meth)acrylic groups in the molecule; and a (C) radical initiator, and a polarizing plate and an optical member including the radical-curable adhesive composition.

First claim

The invention claimed is:

1. A radical-curable adhesive composition comprising:
a (A) radical-polymerizable compound having at least one hydrophilic functional group in the molecule;
a (B) phosphate-based compound having three (meth)acrylic groups in the molecule; and
a (C) radical initiator,
wherein the (B) phosphate-based compound is a compound represented by Chemical Formula I:

wherein R 1 , R 2 and R 3 are each independently a substituted or unsubstituted C 1-10 alkylene group, a substituted or unsubstituted C 4-14 cycloalkylene group, a substituted or unsubstituted C 6-14 arylene group or a combination thereof; R 4 , R 5 and R 6 are each independently hydrogen or a methyl group; and X 1 , X 2 and X 3 are each independently oxygen (O) or nitrogen (N).

2. The radical-curable adhesive composition of claim 1 , comprising:
the (A) radical-polymerizable compound in 40 to 93 parts by weight;
the (B) phosphate-based compound in 1 to 40 parts by weight; and
the (C) radical initiator in 0.5 to 20 parts by weight, with respect to 100 parts by weight of the radical-curable adhesive composition.

3. The radical-curable adhesive composition of claim 1 , wherein the (A) radical-polymerizable compound is a mixture of a (a-1) radical-polymerizable first compound including at least one hydroxyl group and at least one (meth)acrylic group in the molecule; and a (a-2) radical-polymerizable second compound including at least two hydroxyl groups, at least one benzene ring or cyclohexane ring, and at least two (meth)acrylic groups in the molecule.

4. The radical-curable adhesive composition of claim 3 , wherein the (a-1) first compound is one or more types selected from the group consisting of the following [Chemical Formula 1] to [Chemical Formula 21]:

5. The radical-curable adhesive composition of claim 3 , wherein the (a-2) second compound is one or more types selected from the group consisting of the following [Chemical Formula 22] to [Chemical Formula 24]:

6. The radical-curable adhesive composition of claim 1 , further comprising a (D) phosphate-based compound having one or two (meth)acrylic groups in the molecule.

7. The radical-curable adhesive composition of claim 6 , wherein the (D) a phosphate-based compound is included in 5 to 40 parts by weight with respect to 100 parts by weight of the radical-curable adhesive composition.

8. The radical-curable adhesive composition of claim 6 , wherein the (D) phosphate-based compound is one or more types selected from the group consisting of the following [Chemical Formula II] and [Chemical Formula III]:

wherein, in [Chemical Formula II], R 7 and R 8 are each independently a substituted or unsubstituted C 1-10 alkylene group, a substituted or unsubstituted C 4-14 cycloalkylene group, a substituted or unsubstituted C 6-14 arylene group or a combination thereof; R 9 and R 10 are each independently hydrogen or a methyl group; and X 4 and X 5 are each independently oxygen (O) or nitrogen (N); and

in [Chemical Formula III], R 11 is a substituted or unsubstituted C 1-10 alkylene group, a substituted or unsubstituted C 4-14 cycloalkylene group, a substituted or unsubstituted C 6-14 arylene group or a combination thereof; R 12 is hydrogen or a methyl group; X 6 is oxygen (O) or nitrogen (N).

9. The radical-curable adhesive composition of claim 1 , further comprising a (E) multifunctional (meth)acryl-based compound.

10. The radical-curable adhesive composition of claim 9 , wherein the (E) multifunctional (meth)acryl-based compound is included in 5 to 40 parts by weight with respect to 100 parts by weight of the radical-curable adhesive composition.

11. The radical-curable adhesive composition of claim 9 , wherein the (E) multifunctional (meth)acryl-based compound is one or more types selected from the group consisting of compounds represented by the following [Chemical Formula IV] to [Chemical Formula VI]:

wherein, in [Chemical Formula IV], R 13 and R 14 are each independently a (meth)acryloyloxy group or a (meth)acryloyloxyalkyl group;

in [Chemical Formula V], R 15 , R 16 and R 17 are each independently a (meth)acryloyloxy group or a (meth)acryloyloxyalkyl group, and R 18 is a (meth)acryloyloxy group, a (meth)acryloyloxyalkyl group, a hydroxyl group or a substituted or unsubstituted C 1-10 alkyl group; and

in [Chemical Formula VI], R 19 is substituted or unsubstituted C 1-10 alkylene, and R 20 and R 21 are each independently a (meth)acryloyloxy group or a (meth)acryloyloxyalkyl group.

12. The radical-curable adhesive composition of claim 1 , wherein a thickness of an adhesive layer formed by the radical-curable adhesive composition is 10 μm or less.

13. The radical-curable adhesive composition of claim 1 , which has a glass transition temperature of 50° C. or higher after curing.

14. The radical-curable adhesive composition of claim 1 , which has viscosity of 70 cP or less.

15. A polarizing plate comprising:
a polarizer;
an adhesive layer formed on at least one surface of the polarizer; and
a polarizer protective film formed on the adhesive layer;
wherein the adhesive layer is formed using the radical-curable adhesive composition of claim 1 .

16. An optical member comprising:
a display panel; and
a polarizer attached to an external-most surface of the display panel through a medium of an adhesive layer;
wherein the adhesive layer is formed using the radical-curable adhesive composition of claim 1 .

Assignees

• Lg Chemical Ltd

Inventors

• Huh Eun-Soo
• Park Kwang-Seung
• Lee Mi-Rin
• Park Jun-Wuk

Classifications

• C09J4/00 Primary

  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

• C09J133/24

  Homopolymers or copolymers of amides or imides · CPC title

• C09J133/06

  of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical · CPC title

• G02F1/133528

  Polarisers · CPC title

• C09J133/068

  containing glycidyl groups · CPC title