Modified polyvinyl alcohol resins and adhesive, polarizer, and display device containing the same

Patent metadata

Field	Value
Publication number	US-10030181-B2
Application number	US-201614995009-A
Country	US
Kind code	B2
Filing date	Jan 13, 2016
Priority date	Feb 20, 2009
Publication date	Jul 24, 2018
Grant date	Jul 24, 2018

Abstract

Provided are a modified polyvinyl alcohol-based resin with an acrylic group introduced thereto and including a hydroxyl group formed during the introduction of the acrylic group, an adhesive including the modified polyvinyl alcohol-based resin having excellent adhesion, humidity resistance, and water resistance, an adhesive including a polyvinyl alcohol-based resin, and a compound having an epoxy group, and an acrylic group, a polarizing plate and an image display device including the adhesive. The adhesive for a polarizing plate according to an embodiment of the present invention has excellent adhesion, humidity resistance, and water resistance as well as having excellent solubility with respect to water and an increase in adhesion while physical properties of a typical polyvinyl alcohol-based resin are maintained.

First claim

The invention claimed is:

1. A polarizing plate comprising a polarizer and a protective film adhered to each other with an adhesive, the adhesive comprising:
a modified polyvinyl alcohol comprising a polyvinyl alcohol-based resin having a weight average molecular weight of 20,000 to 100,000, modified with an acrylic group introduced thereto and comprising a hydroxyl group formed by introduction of the acrylic group, the modified polyvinyl alcohol-based resin consisting of: (i) a repeating unit of Chemical Formula A, (ii) 0.1 mol % to 50 mol %, with respect to 100 mol % of total modified polyvinyl alcohol-based resin, of at least one repeating unit selected from Chemical Formula B1, Chemical Formula B2, and Chemical Formula B3, and (iii) a repeating unit of Chemical Formula C, wherein

in which n is an integer between about 490 and about 1700; m is an integer between about 10 and about 900; n+m is an integer between about 500 and about 1800; R 1 is substituted or unsubstituted C 1 -C 20 alkandiyl, a substituted or unsubstituted 5- to 7-membered cyclic group, a substituted or unsubstituted 5- to 7-membered heterocyclic group including a heteroatom selected from the group consisting of N, S, or O, a substituted or unsubstituted C 6 -C 14 aromatic group, or a substituted or unsubstituted 5- to 7-membered heteroaromatic group including at least one heteroatom selected from the group consisting of N, S, or O; and R 2 is a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted 5- to 7-membered cyclic group, a substituted or unsubstituted 5- to 7-membered heterocyclic group including at least one heteroatom selected from the group consisting of N, S, or O, a substituted or unsubstituted C 6 -C 14 aromatic group, or a substituted or unsubstituted 5- to 7-membered heteroaromatic group including at least one heteroatom selected from the group consisting of N, S, or O; and when R 1 and R 2 are substituted with a substituent, the substituent is a C 1 -C 20 alkyl group, a halogen atom selected from the group consisting of F, Cl, Br, or I, a 5- to 7-membered cyclic group, a 5- to 7-membered heterocyclic group including at least one heteroatom selected from the group consisting of N, S, or O, a C 6 -C 14 aromatic group, or a 5- to 7-membered heteroaromatic group including at least one heteroatom selected from the group consisting of N, S, or O, and 1 is an integer between about 1 and 80, and R 3 is a carboxylic acid group, an acrylic group, or a urethane group,
wherein the modified polyvinyl alcohol-based resin is obtained by performing a reaction between the polyvinyl alcohol-based resin and about 0.001 to 10 parts by weight, with respect to 100 parts by weight of the polyvinyl alcohol-based resin, of a compound having an epoxy group and an acrylic group, and
an initiator selected from the group consisting of 2,2′-azo-bis(isobutyronitrile) (AIBN)-based and persulfate-based water-soluble initiators, and
wherein the modified polyvinyl alcohol-based resin is free of acetocetyl groups.

2. The polarizing plate of claim 1 , wherein a sum of the number n of the repeating unit of Chemical Formula A and the number 1 of the repeating unit of Chemical Formula C is an integer between about 490 and about 1700, the number 1 of the repeating unit of Chemical Formula C in the sum of n and 1 is an integer between about 1 and about 80, the number m of the repeating unit of Chemical Formulas B1, B2 and_B3 is an integer between about 10 and about 900, and a sum of n, m, and 1 is an integer between about 500 and about 1800.

3. The polarizing plate of claim 1 , wherein an average degree of polymerization of the polyvinyl alcohol-based resin is in a range of about 500 and about 1800.

4. The polarizing plate of claim 1 , wherein the compound having an epoxy and an acrylic group is represented as Chemical Formula 2:

in which R 1 is substituted or unsubstituted C 1 -C 20 alkandiyl, a substituted or unsubstituted 5- to 7-membered cyclic group, a substituted or unsubstituted 5- to 7-membered heterocyclic group including a heteroatom selected from the group consisting of N, S, or O, a substituted or unsubstituted C 6 -C 14 aromatic group, or a substituted or unsubstituted 5- to 7-membered heteroaromatic group including at least one heteroatom selected from the group consisting of N, S, or O; R 2 is a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted 5- to 7-membered cyclic group, a substituted or unsubstituted 5- to 7-membered heterocyclic group including at least one heteroatom selected from the group consisting of N, S, or O, a substituted or unsubstituted C 6 -C 14 aromatic group, or a substituted or unsubstituted 5- to 7-membered heteroaromatic group including at least one heteroatom selected from the group consisting of N, S, or O; and when R 1 and R 2 are substituted with a substituent, the substituent is a C 1 -C 20 alkyl group, a halogen atom selected from the group consisting of F, Cl, Br, or I, a 5- to 7-membered cyclic group, a 5- to 7-membered heterocyclic group including at least one heteroatom selected from the group consisting of N, S, or O, a C 6 -C 14 aromatic group, or a 5- to 7-membered heteroaromatic group including at least one heteroatom selected from the group consisting of N, S, or O.

5. The polarizing plate of claim 1 , wherein the initiator is added to a maximum of about 10 wt %.

6. The polarizing plate of claim 1 , wherein the modified polyvinyl alcohol-based resin is water soluble.

7. The polarizing plate of claim 1 , wherein the adhesive is water soluble.

8. A display device comprising the polarizing plate of claim 1 .

Assignees

• Lg Chemical Ltd

Inventors

• Park Seong-Jun
• Kwon Ki-Ok
• Rah Kyun-Il

Classifications

• C09J129/04 Primary

  Polyvinyl alcohol; Partially hydrolysed homopolymers or copolymers of esters of unsaturated alcohols with saturated carboxylic acids · CPC title

• Y10T428/31935

  Ester, halide or nitrile of addition polymer · CPC title

• G02B1/14

  Protective coatings, e.g. hard coatings · CPC title

• G02B5/305

  including organic materials, e.g. polymeric layers · CPC title

• C09J151/003 Primary

  grafted on to macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds (C09J151/04, C09J151/06 take precedence) · CPC title