# US 10,246,606 B2 · Transparent flexible hard coated film and method of producing the same

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- Number: US 10,246,606 B2
- Document ID: US10246606B2
- Status: Granted
- Kind: B2
- Application number: 15/456,891
- Filed: 2017-03-13
- Published: 2017-06-29
- Granted: 2019-04-02
- Earliest claimed: 2013-02-20
- Assignees: Korea Advanced Institute of Science and Technology
- Applicants: Korea Advanced Institute of Science and Technology
- Inventors: Byeong-Soo Bae; Gwang-Mun Choi; Ji-Hoon Ko
- Web page: https://patentgrep.com/patent/US10246606B2

## CPC

- C09D 163/00: Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
- C08J 7/0427: {with only one layer of a composition containing a polymer binder (with more layers C08J7/042)}
- C08J 7/046: Forming abrasion-resistant coatings; Forming surface-hardening coatings
- C09D 183/06: containing silicon bound to oxygen-containing groups (C09D183/12 takes precedence)
- C08G 65/02: from cyclic ethers by opening of the heterocyclic ring
- C08G 77/14: containing silicon bound to oxygen-containing groups
- C08J 2483/04: Polysiloxanes
- C09D 4/00: Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond {; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16}
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)
- C08J: WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H (working, e.g. shaping, of plastics B29)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS

## Abstract

The invention relates to a transparent flexible hard coated film and a method of producing the same, and more particularly, to a transparent flexible hard coated film including a scratch-resistant surface and a method of producing the same.

## Claims

### Claim 1

An ionic polymerizable siloxane hard coating composition for forming a transparent flexible hard coated film, the composition comprising:
oligosiloxane [component (A)] having on average at least one alicyclic epoxy group per molecule;
a reactive diluent [component (B)] that is (3,4-epoxycyclohexyl)methyl 3,4-epoxycyclohexylcarboxylate or that has on average at least one oxetane group per molecule; and
an ionic polymerization initiator [component (C)],
wherein the ionic polymerizable siloxane hard coating composition is produced by a method including mixing the component (C) of from 0.1 part by weight to 10 parts by weight with respect to 100 parts by weight of the component (A),
wherein the component (A) has an average unit chemical formula represented by the following Chemical Formula 1:
(R1SiO3/2)a(R22SiO2/2)b(R33SiO1/2)c(SiO4/2)d(R4O1/2)e, [Chemical Formula 1]
wherein in Chemical Formula 1,
R1 is an alicyclic epoxy group, and R2 and R3 are each independently selected from the group consisting of a substitutable C1-20 alkyl group, a substitutable C2-20 alkenyl group, a substitutable C2-20 alkynyl group, and a substitutable C6-20 aryl group, a substitutable substituent in the R2, and R3 is at least one member selected from the group consisting of a C1-20 alkyl group, a C3-8 cycloalkyl group, a C1-20 alkoxy group, an amino group, an acryl group, a (meth)acryl group, halogen, an allyl group, a mercapto group, an ether group, an ester group, a carbonyl group, a carboxyl group, a vinyl group, a nitro group, a sulfone group, a hydroxyl group, a cyclobutene group, an alkyd group, an urethane group, an oxetane group, a phenyl group, and combinations thereof,
R4 is a straight or branched C1-7 alkyl group or hydrogen,
a is a positive number,
b is 0 or a positive number,
c is 0 or a positive number,
d is 0 or a positive number,
e is 0 or a positive number,
(b+c+d)/a is a number of from 0 to 1,
e/(a+b+c+d) is a number of from 0 to 0.4, and
the alicyclic epoxy group is not a glycidyl group.

### Claim 2 (depends on 1)

The ionic polymerizable siloxane hard coating composition of claim 1, wherein the ionic polymerizable siloxane hard coating composition is produced by a method further including mixing the component (A) with the component (B) prior to mixing the component (A) with the component (C).

### Claim 3 (depends on 1)

The ionic polymerizable siloxane hard coating composition of claim 1, wherein the ionic polymerizable siloxane hard coating composition is produced by a method including mixing the component (C) of from 0.1 part by weight to 10 parts by weight with respect to 100 parts by weight of a mixture of the component (A) and the component (B).

### Claim 4 (depends on 1)

The ionic polymerizable siloxane hard coating composition of claim 1, wherein the component (C) includes a cationic polymerization initiator or an anionic polymerization initiator.

### Claim 5 (depends on 1)

A method of producing a transparent flexible hard coated film using the ionic polymerizable siloxane hard coating composition of claim 1, comprising:
coating the ionic polymerizable siloxane hard coating composition on a substrate film; and
polymerizing a coating layer of the ionic polymerizable siloxane hard coating composition.

### Claim 6 (depends on 5)

The method of claim 5, wherein the substrate film includes a main component including at least one resin selected from the group consisting of acryl-based resin, styrene-based resin, acrylonitrile butadiene styrene-based resin, styrene acrylonitrile-based resin, polypropylene-based resin, polyethylene-based resin, polyacetal-based resin, polycarbonate-based resin, polyimide-based resin, polyvinyl chloride-based resin, polyester-based resin, polyurethane-based resin, norbornene-based resins cycloolefin-based resin, epoxy-based resin, and ether sulfone-based resin.

### Claim 7 (depends on 5)

The method of claim 5, wherein the polymerizing is performed by a light irradiation or a heat treatment.

### Claim 8 (depends on 1)

The ionic polymerizable siloxane hard coating composition of claim 1, wherein the alicyclic epoxy group is represented by the following:

### Claim 9 (depends on 5)

A transparent flexible hard coated film produced by the method of claim 5.