IP Library Granted Patent US 9,187,672
Granted Patent B2
US 9,187,672 · App. 13/672,953 · Granted Nov 17, 2015

Hard coating film, composition for hard coating film, polarizing plate including the same, and liquid crystal display including the same

Inventors: Sang Shin Kim (Uiwang-si, KR); Dong Yoon Shin (Uiwang-si, KR); Hae Ryong Chung (Uiwang-si, KR)
Assignee: CHEIL INDUSTRIES, INC.
C09D135/02C09D133/14G02B1/105B82Y30/00C08L2312/00Y10S977/773
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Quick Facts
Patent No.
US 9,187,672
App. No.
13/672,953
Filed
Nov 9, 2012
Granted
Nov 17, 2015
Kind
B2
Art Unit
1762
USPC
526/318.43
Abstract

A hard coating film may include a cured product of a polyester polyol modified hyperbranched (meth)acrylate represented by Formula 1:

Claims (74)

1. A hard coating film, comprising:

a cured product of a polyester polyol modified hyperbranched (meth)acrylate represented by Formula 1:

wherein, in Formula 1:

P is a C 2 -C 50 polyester,

E is a divalent ester moiety,

Q 1 , Q 2 , Q 3 , and Q 4 are each independently selected from the group of a C 2 -C 50 aliphatic hydrocarbon and a C 6 -C 50 aromatic hydrocarbon,

m, n, p, q, r, s, t, and w are each independently an integer from 1 to 10, and

R, R′, R″, and R″' are each independently selected from the group of hydrogen and a C 1 -C 5 alkyl group,

wherein film curling of the hard coating film is from 0 to about 20 mm when the hard coating film has a thickness of about 2 μm to about 30 μm, and is stacked on a base film having a thickness of about 40 μm or less, and

wherein about 10 wt % to about 30 wt % of the hard coating film is from the polyester polyol modified hyperbranched (meth)acrylate.

2. The hard coating film as claimed in claim 1 , wherein the polyester polyol modified hyperbranched (meth)acrylate has a weight average molecular weight of about 2000 g/mol to about 3000 g/mol.

3. The hard coating film as claimed in claim 1 , wherein the polyester polyol modified hyperbranched (meth)acrylate is represented by Formula 2:

wherein, in Formula 2, x, y, and z are each independently an integer from 0 to 5, with the proviso that x +y +z >0.

4. The hard coating film as claimed in claim 1 , wherein the hard coating film is formed of a composition, the composition including:

the polyester polyol modified hyperbranched (meth)acrylate;

a hyperbranched (meth)acrylate oligomer represented by Formula 3;

reactive nanoparticles;

a polyfunctional monomer; and

a photopolymerization initiator,

wherein, in Formula 3:

the core is selected from the group of a C 3 -C 50 aliphatic hydrocarbon and a C 6 -C 50 aromatic hydrocarbon,

R 1 , R 1 ′, R 1 ″, R 1 ″', R 2 , and R 2 ′ are each independently selected from the group of a C 1 -C 50 aliphatic hydrocarbon and a C 6 -C 50 aromatic hydrocarbon, and

E is a divalent ester moiety.

5. The hard coating film as claimed in claim 4 , wherein, in Formula 3, at least one selected from the group of the core, R 1 , R 1 ′, R 1 ″, R 1 ″', R 2 , and R 2 ′ includes at least one heteroatom.

6. The hard coating film as claimed in claim 4 , wherein the hyperbranched (meth)acrylate oligomer has a weight average molecular weight of about 5000 g/mol to about 10,000 g/mol.

7. The hard coating film as claimed in claim 4 , wherein the reactive nanoparticles have an average particle diameter of about 10 nm to about 100 nm.

8. The hard coating film as claimed in claim 4 , wherein the reactive nanoparticles include inorganic nanoparticles, and about 3% to about 50% of a surface area of the inorganic nanoparticles is surface-treated with a (meth)acrylate compound.

9. The hard coating film as claimed in claim 8 , wherein the inorganic nanoparticles include at least one selected from the group of SiO 2 , Al 2 O 3 , CaCO 3 , and TiO 2 .

10. The hard coating film as claimed in claim 4 , wherein the polyfunctional monomer includes at least one selected from the group of a hydroxyl group-containing polyfunctional (meth)acrylate compound and a fluorine modified polyfunctional (meth)acrylate compound.

11. The hard coating film as claimed in claim 4 , wherein the composition includes:

about 10 wt % to about 30 wt % of the polyester polyol modified hyperbranched (meth)acrylate,

about 15 wt % to about 60 wt % of the hyperbranched (meth)acrylate oligomer,

about 5 wt % to about 60 wt % of the reactive nanoparticles,

about 1 wt % to about 40 wt % of the polyfunctional monomer, and

about 1 phr by weight to about 10 phr by weight of the photopolymerization initiator, based on a total weight of the polyester polyol modified hyperbranched (meth)acrylate, the hyperbranched (meth)acrylate oligomer, the reactive nanoparticles, and the polyfunctional monomer.

12. The hard coating film as claimed in claim 4 , wherein the composition further includes a reactive fluorine compound.

13. The hard coating film as claimed in claim 12 , wherein the reactive fluorine compound is represented by Formula 4:

Ar—Rf—Ar,  [Formula 4]

wherein, in Formula 4:

Ar is CH 2 =CR 3 COO,

R 3 is selected from the group of a hydrogen atom and a C 1 -C 3 alkyl group,

Rf is a perfluoroalkylene group having a structure represented by one selected from the group of Formulae 5-A, 5-B, 5-C, 5-D, and 5-E:

* is a bonding site for Ar,

R F1 is a straight or branched C 1 -C 10 perfluoroalkylene group, and

R F2 , R F3 , R F4 , and R F5 each independently are H, a straight or branched C 1 -C 14 perfluoroalkyl group.

14. The hard coating film as claimed in claim 12 , wherein the reactive fluorine compound is present in an amount of about 0.01 parts by weight to about 5 parts by weight, based on 100 parts by weight of the composition.

15. A composition for hard coating films, comprising:

a polyester polyol modified hyperbranched (meth)acrylate represented by Formula 1;

a hyperbranched (meth)acrylate oligomer represented by Formula 3;

reactive nanoparticles;

a polyfunctional monomer; and

a photopolymerization initiator:

wherein, in Formula 1,

P is a C 2 -C 50 polyester,

E is a divalent ester moiety,

Q 1 , Q 2l, Q 3 , and Q 4 are each independently selected from the group of a C 2 -C 50 aliphatic hydrocarbon and a C 6 -C 50 aromatic hydrocarbon,

m, n, p, q, r, s, t, and w are each independently an integer from 1 to 10, and

R, R′, R″, and R″' are each independently selected from the group of hydrogen and a C 1 -C 5 alkyl group,

wherein, in Formula 3:

the core is selected from the group of a C 3 -C 50 aliphatic hydrocarbon and a C 6 -C 50 aromatic hydrocarbon,

R 1 , R 1 ′, R 1 ″, R 1 ″', R 2 , and R 2 ′ are each independently selected from the group of a C 1 -C 50 aliphatic hydrocarbon and a C 6 -C 50 aromatic hydrocarbon, and

E is a divalent ester moiety.

16. The composition as claimed in claim 15 , wherein the composition includes:

about 10 wt % to about 30 wt % of the polyester polyol modified hyperbranched (meth)acrylate,

about 15 wt % to about 60 wt % of the hyperbranched (meth)acrylate oligomer,

about 5 wt % to about 60 wt % of the reactive nanoparticles,

about 1 wt % to about 40 wt % of the polyfunctional monomer, and

about 1 phr by weight to about 10 phr by weight of the photopolymerization initiator, based on a total weight of the polyester polyol modified hyperbranched (meth)acrylate, the hyperbranched (meth)acrylate oligomer, the reactive nanoparticles, and the polyfunctional monomer.

17. The composition as claimed in claim 15 , further comprising a reactive fluorine compound.

18. A polarizing plate, comprising:

a polarizer;

a base film on at least one surface of the polarizer; and

the hard coating film as claimed in claim 1 .

19. A liquid crystal display, comprising the polarizing plate as claimed in claim 18 .

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 4, 2026
From: WUXI HENGXIN OPTOELECTRONIC MATERIALS CO., LTD.
To: HOARDSUN HENGXIN(WUXI) MATERIALS CO., LTD.
Reel/Frame 075049/0450 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 14, 2025
From: SAMSUNG SDI CO., LTD.
To: WUXI HENGXIN OPTOELECTRONIC MATERIALS CO., LTD.
Reel/Frame 073062/0496 →
MERGER Recorded Jun 16, 2025
From: CHEIL INDUSTRIES INC.
To: SAMSUNG SDI CO., LTD.
Reel/Frame 071636/0099 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 9, 2012
From: KIM, SANG SHIN; SHIN, DONG YOON; CHUNG, HAE RYONG
To: CHEIL INDUSTRIES, INC.
Reel/Frame 029269/0751 →
Priority Claims (1)
KR 10-2011-0117190 · Nov 10, 2011 · national
Continuity (1)
Related Publication 20130120838A1 · May 16, 2013