# US 10,246,611 B2 · Transparent film

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- Number: US 10,246,611 B2
- Document ID: US10246611B2
- Status: Granted
- Kind: B2
- Application number: 15/525,177
- Filed: 2015-11-09
- Published: 2017-11-02
- Granted: 2019-04-02
- Earliest claimed: 2014-11-12
- Assignees: Sumitomo Chemical Company, Limited
- Applicants: Sumitomo Chemical Company, Limited
- Inventors: Yoshihiro Harada; Yasuharu Shimazaki; Tomonori Miyamoto
- Web page: https://patentgrep.com/patent/US10246611B2

## CPC

- C09D 183/08: containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen
- C03C 17/30: with silicon-containing compounds
- C09D 5/00: Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced {(electrically insulating plastics, resins or waxes H01B3/30)}; Filling pastes
- C09D 5/165: {containing hydrolysable groups (C09D5/1643 takes precedence)}
- C09D 5/1675: {Polyorganosiloxane-containing compositions}
- C03C 2217/75: Hydrophilic and oleophilic coatings
- C03C 2218/116: by spin-coating, centrifugation
- C08G 77/24: halogen-containing groups
- 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)
- C03C: CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS

## Abstract

The object of present invention is to provide a transparent film which further improves a slip characteristic of waterdrop. The present invention is a transparent film having a polysiloxane backbone, the transparent film having a structure (a) in which a fluorine-containing group having a perfluoroalkyl group or a perfluoropolyether group on the free end side thereof is bonded to a silicon atom of the polysiloxane backbone, and the transparent film having a slip rate of 0.2 mm/s or more for a 120 μl waterdrop on an 8° incline. In preferred embodiment, the fluorine-containing groups are bonded to some silicon atoms of the polysiloxane backbone in structure (a), and the transparent film has a structure (b) in which carbon fluoride-containing groups or hydrolysable silane oligomer residue are bonded to some of the remaining silicon atoms of the polysiloxane backbone.

## Claims

### Claim 1

A transparent film having a polysiloxane backbone,
wherein the transparent film has a structure (a) in which a fluorine-containing group having a perfluoroalkyl group or a perfluoropolyether group on the free end side thereof is bonded to a silicon atom of the polysiloxane backbone,
the fluorine-containing group having the perfluoroalkyl group on the free end side thereof is a group represented by the following formula (3-1) or (4-1),
in the formula (3-1),
Rf represents a fluorine atom or an alkyl group which has 1 to 20 carbon atoms and is substituted with one or more fluorine atoms,
Rf2 each independently represents a fluorine atom or an alkyl group which has 1 to 20 carbon atoms and is substituted with one or more fluorine atoms, R3 each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms,
D each independently represents —O—, —COO—, —OCO—, —NR—, —NRCO—, or —CONR—, wherein R represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a fluorine-containing alkyl group having 1 to 4 carbon atoms,
a2, c2, d2, and e2 are each independently an integer of not less than 0 and not more than 600, and the sum total of a2, b2, c2, d2, and e2 is 13 or more,
b2 is not less than 20 and not more than 600,
in the formula (4-1),
Rf represents a fluorine atom or an alkyl group which has 1 to 20 carbon atoms and is substituted with one or more fluorine atoms,
Rf3 each independently represents a fluorine atom or an alkyl group which has 1 to 20 carbon atoms and is substituted with one or more fluorine atoms, R5 each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms,
G each independently represents —O—, —COO—, —OCO—, —NR—, —NRCO—, or —CONR—, wherein R represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a fluorine-containing alkyl group having 1 to 4 carbon atoms,
Y each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms,
Z represents a hydrogen atom or a halogen atom,
a3, c3, d3, and e3 are each independently an integer of not less than 0 and not more than 600, and the sum total of a3, b3, c3, d3, and e3 is 13 or more,
b3 is not less than 20 and not more than 600,
h3 is an integer of not less than 0 and not more than 2,
q is an integer of not less than 1 and not more than 10,
the fluorine-containing groups are bonded to some silicon atoms of the polysiloxane backbone in the structure (a),
the transparent film has a structure (b) in which carbon fluoride-containing groups or hydrolysable silane oligomer residue are bonded to some of the remaining silicon atoms of the polysiloxane backbone,
the molecular length of the structure (b) is shorter than the molecular length of the structure (a), and
the transparent film has a slip rate of 0.2 mm/s or more for a 120 μl waterdrop on an 8° incline.

### Claim 2 (depends on 1)

The transparent film according to claim 1, wherein the slip rate for a 120 μl waterdrop on an 8° incline is 0.5 mm/s or more.

### Claim 3 (depends on 1)

The transparent film according to claim 1, wherein the fluorine-containing group of the structure (a) comprises a hydrocarbon group.

### Claim 4 (depends on 1)

The transparent film according to claim 1, wherein the structure (b) has a hydrolyzable silane oligomer residue having an alkyl group or a fluorine-containing alkyl group, and the alkyl group or the fluorine-containing alkyl group is shorter in the number of atoms than the longest straight chain part of the fluorine-containing group of the structure (a).

### Claim 5 (depends on 1)

The transparent film according to claim 1, wherein the structure (b) has the carbon fluoride-containing group, and the longest straight chain part of the carbon fluoride-containing group is shorter in the number of atoms than the longest straight chain part of the fluorine-containing group of the structure (a).

### Claim 6 (depends on 1)

The transparent film according to claim 1, wherein the carbon fluoride-containing group or the hydrolyzable silane oligomer residue of the structure (b) is each represented by the following formula (1-1) or (2-1),
in formulae (1-1) and (2-1),
Rf1 each independently represents a fluorine atom or an alkyl group substituted with one or more fluorine atoms and having 1 to 20 carbon atoms;
R1 each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms;
A each independently represents —O—, —COO—, —OCO—, —NR—, —NRCO—, and —CONR—, wherein R represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a fluorine-containing alkyl group having 1 to 4 carbon atoms;
X each independently represents a hydrolyzable group, an alkyl group having 1 to 4 carbon atoms, or a fluorine-containing alkyl group having 1 to 4 carbon atoms;
a1, b1, c1, d1, e1, and g1 each independently are an integer of not less than 0 and not more than 100,
each of repeating units enclosed in parentheses with a1, b1, c1, d1, or e1 added thereto is present in arbitrary order in the formula, and
the sum total of a1, b1, c1, d1, and e1 is 100 or less.

### Claim 7 (depends on 3)

The transparent film according to claim 3, wherein the molecular length of the structure (b) is shorter than the molecular length of the structure (a).

### Claim 8 (depends on 7)

The transparent film according to claim 7, wherein the structure (b) has the carbon fluoride-containing group, and the longest straight chain part of the carbon fluoride-containing group is shorter in the number of atoms than the longest straight chain part of the fluorine-containing group of the structure (a).

### Claim 9 (depends on 8)

The transparent film according to claim 8, wherein the carbon fluoride-containing group or the hydrolyzable silane oligomer residue of the structure (b) is each represented by the following formula (1-1) or (2-1),
in formulae (1-1) and (2-1),
Rf1 each independently represents a fluorine atom or an alkyl group substituted with one or more fluorine atoms and having 1 to 20 carbon atoms;
R1 each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms;
A each independently represents —O—, —COO—, —OCO—, —NR—, —NRCO—, and —CONR—, wherein R represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a fluorine-containing alkyl group having 1 to 4 carbon atoms;
X each independently represents a hydrolyzable group, an alkyl group having 1 to 4 carbon atoms, or a fluorine-containing alkyl group having 1 to 4 carbon atoms;
a1, b1, c1, d1, e1, and g1 each independently are an integer of not less than 0 and not more than 100,
each of repeating units enclosed in parentheses with a1, b1, c1, d1, or e1 added thereto is present in arbitrary order in the formula, and
the sum total of a1, b1, c1, d1, and e1 is 100 or less.

### Claim 10 (depends on 1)

The transparent film according to claim 1, wherein
e2 is equal to or more than ⅕ of the sum total of a2, b2, c2, and d2 and equal to or less than the sum total of a2, b2, c2, and d2,
e2 is not less than 4 and not more than 600,
e3 is not less than ⅕ of the sum total of a3, b3, c3, and d3 and equal to or less than the sum total of a3, b3, c3, and d3, and
e3 is not less than 4 and not more than 600.