# US 10,767,017 B2 · Resin composition, method for producing resin composition, film formation method, and cured product

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- Number: US 10,767,017 B2
- Document ID: US10767017B2
- Status: Granted
- Kind: B2
- Application number: 15/855,291
- Filed: 2017-12-27
- Published: 2018-06-28
- Granted: 2020-09-08
- Earliest claimed: 2016-12-28
- Assignees: Tokyo Ohka Kogyo Co., Ltd.
- Applicants: Tokyo Ohka Kogyo Co., Ltd.
- Inventors: Kunihiro Noda; Hiroki Chisaka; Kazuya Someya; Dai Shiota
- Web page: https://patentgrep.com/patent/US10767017B2

## CPC

- C08G 77/18: to alkoxy or aryloxy groups
- C08G 77/08: characterised by the catalysts used
- C08G 77/42: Block-or graft-polymers containing polysiloxane sequences (polymerising aliphatic unsaturated monomers on to a polysiloxane C08F283/12)
- C08G 77/60: in which all the silicon atoms are connected by linkages other than oxygen atoms
- C08L 83/10: Block- or graft-copolymers containing polysiloxane sequences (obtained by polymerising a compound having a carbon-to-carbon double bond on to a polysiloxane C08L51/08, C08L53/00)
- C08L 83/14: in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms (C08L83/10 takes precedence)
- C08L 83/16: in which all the silicon atoms are connected by linkages other than oxygen atoms
- C09D 183/06: containing silicon bound to oxygen-containing groups (C09D183/12 takes precedence)
- C07F 7/21: Cyclic compounds having at least one ring containing silicon, but no carbon in the ring
- C08G 77/04: Polysiloxanes
- C08G 77/06: Preparatory processes
- C09D 183/04: Polysiloxanes
- C09D 183/10: Block or graft copolymers containing polysiloxane sequences (obtained by polymerising a compound having a carbon-to-carbon double bond on to a polysiloxane C09D151/08, C09D153/00)
- Y02E 10/50: Photovoltaic [PV] energy
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- 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)
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- Y02E: REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION

## Abstract

A resin composition including a silicon-containing resin component and a solvent, the silicon-containing resin component including at least one of (I) and (II) mentioned below, the solvent including at least one of a terpene compound having at least one of a hydroxy group and an acetoxy group, and a cyclic skeleton-containing acetate compound (excluding the terpene compound): (I) a polysilane-polysiloxane resin having a polysilane structure and a polysiloxane structure, and (II) a mixture of a resin having a polysilane structure and a resin having a polysiloxane structure.

## Claims

### Claim 1

A resin composition comprising a silicon-containing resin component and a solvent, wherein
the silicon-containing resin component comprises (II) a mixture of a resin having a polysilane structure (II-1) and a resin having a polysiloxane structure (II-2), and
the solvent comprises a terpene compound having at least one group selected from the group consisting of a hydroxy group and an acetoxy group,
wherein the polysiloxane structures (II-2) comprises a hydrolyzed and condensed structure of at least one silicon compound selected from the group consisting of silicon compounds represented by the following general formulas (A-1-1) to (A-1-4):
R1R2R3SiX1 (A-1-1)
R4R5SiX22 (A-1-2)
R6SiX33 (A-1-3)
SiX44 (A-1-4)
wherein X1 to X4 are each independently a hydrolyzable group, and wherein R1, R2, R3, R4, R5, and R6 are each independently a hydrogen atom or an organic group, and hydrogen atoms in the organic group may be substituted with a halogen atom, and
wherein the polysilane structure (II-1) comprises a structure corresponding to at least one selected from the group consisting of polysilane compounds represented by the following general formulas (A-2-1) and (A-2-2):
(R7R8R9Si)a1(R10R11Si)a2(R12Si)a3(Si)a4 (A-2-1)
wherein R7, R8, R9, R10, R11, and R12 are each independently a hydrogen atom, a hydroxyl group, or a monovalent organic group, Si atoms do not bond to each other via R7, R8, R9, R10, R11 or R12, but form an Si—Si bond, and a1, a2, a3, and a4 are each independently a molar fraction, a1+a2+a3+a4=1, 0≤a1≤1, 0≤a2≤1, 0≤a3≤1, and 0≤a4≤1,
wherein Ra1 and Ra2 each independently represents a hydrogen atom, a hydroxyl group, or an organic group, and n represents an integer of 5 to 20.

### Claim 2 (depends on 1)

A method for producing the composition according to claim 1, the method comprising mixing a resin having a polysilane structure with a resin having a polysiloxane structure.

### Claim 3 (depends on 1)

A film formation method using the composition according to claim 1.

### Claim 4 (depends on 1)

A cured product of the composition according to claim 1.

### Claim 5 (depends on 1)

The resin composition according to claim 1, wherein the polysilane structure (II-1) consists essentially of a structures corresponding to at least one type selected from the group consisting of polysilane compounds represented by the general formula (A-2-1) and (A-2-2).

### Claim 6 (depends on 1)

The resin composition according to claim 1, wherein the polysilane structure (II-1) consists essentially of at least one type of polysilane structure represented by the following general formula (B1):
wherein, R10, R11, and R12 each independently represents a hydrogen atom, a hydroxyl group, or a monovalent organic group, * represents a bond, and Si atoms form an Si—Si bond.

### Claim 7 (depends on 1)

The resin composition according to claim 1, wherein
in the general formula (A-2-1), at least one selected from the group consisting of R7, R8 and R9 is an aryl group, at least one selected from the group consisting of R10 and R11 is an aryl group, or R12 is an aryl group, and
in the general formula (A-2-2), at least one selected from the group consisting of Ra1 and Ra2 is an aryl group.

### Claim 8 (depends on 4)

The cured product according to claim 4, the cured product being formed in a film having a thickness of 10 nm to 1500 nm.

### Claim 9

A resin composition comprising a silicon-containing resin component and a solvent, wherein
the silicon-containing resin component comprises (II) a mixture of a resin having a polysilane structure (II-1) and a resin having a polysiloxane structure (II-2), and
the solvent comprises at least one solvent selected from the group consisting of a terpene compound having at least one group selected from the group consisting of a hydroxy group and an acetoxy group, and a cyclic skeleton-containing acetate compound (excluding the terpene compound),
wherein the polysiloxane structure (II-2) comprises a hydrolyzed and condensed structure of at least one silicon compound selected from the group consisting of silicon compounds represented by the following general formulas (A-1-1) to (A-1-4):
R1R2R3SiX1 (A-1-1)
R4R5SiX22 (A-1-2)
R6SiX33 (A-1-3)
SiX44 (A-1-4)
wherein X1 to X4 are each independently a hydrolyzable group, and wherein R1, R2, R3, R4, R5, and R6 are each independently a hydrogen atom or an organic group, and hydrogen atoms in the organic group may be substituted with a halogen atom, and
wherein the polysilane structure (II-1) comprises a structure corresponding to a polysilane compound represented by the following general formula (A-2-2):
wherein Ra1 and Ra2 each independently represents a hydrogen atom, a hydroxyl group, or an organic group, and n represents an integer of 5 to 20.

### Claim 10 (depends on 9)

The resin composition according to claim 9, wherein the cyclic skeleton-containing acetate compound is cycloalkyl acetate represented by the following formula (S1):
in the formula (S1), Rs1 is an alkyl group, p is an integer of 1 to 6, and q is an integer of 0 to (p+1).