# US 10,765,619 B2 · Silicone resin, making method, and cosmetics

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- Number: US 10,765,619 B2
- Document ID: US10765619B2
- Status: Granted
- Kind: B2
- Application number: 15/997,053
- Filed: 2018-06-04
- Published: 2019-12-05
- Granted: 2020-09-08
- Earliest claimed: 2018-06-04
- Assignees: Shin-Etsu Chemical Co., Ltd.
- Applicants: Shin-Etsu Chemical Co., Ltd.
- Inventors: Hiroomi Iyoku; Yuji Ando
- Web page: https://patentgrep.com/patent/US10765619B2

## CPC

- A61K 8/891: saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
- C08L 83/04: Polysiloxanes
- A61Q 1/02: Preparations containing skin colorants, e.g. pigments (preparations in powder form A61Q1/12)
- A61Q 1/06: Lipsticks
- A61Q 1/08: for cheeks, e.g. rouge
- A61Q 1/10: for eyes, e.g. eyeliner, mascara
- A61Q 3/02: Nail coatings
- A61Q 5/00: Preparations for care of the hair
- A61Q 5/12: Preparations containing hair conditioners
- A61Q 15/00: Anti-perspirants or body deodorants (deodorisation of air A61L9/00)
- A61Q 17/04: Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
- A61Q 19/00: Preparations for care of the skin
- A61Q 19/007: {Preparations for dry skin}
- A61Q 19/10: Washing or bathing preparations
- C08G 77/02: Polysilicates
- C09D 183/04: Polysiloxanes
- A61Q 1/12: Face or body powders for grooming, adorning or absorbing
- A61Q 19/08: Anti-ageing preparations
- C08G 77/80: {Siloxanes having aromatic substituents, e.g. phenyl side groups}
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- A61Q: SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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)

## Abstract

A silicone resin represented by formula (1) and having a Mw of 1,000-8,000 is useful in cosmetics. [(C6H5)3SiO1/2]a[R13SiO1/2]b[R22SiO2/2]c[R3SiO3/2]d[SiO4/2]e (1) R1 is a C1-C8 alkyl group, C6-C12 aryl group (exclusive of phenyl) or C1-C8 fluorinated alkyl group, R2 and R3 are each independently a C1-C8 alkyl group, C6-C12 aryl group or C1-C8 fluorinated alkyl group, a=0-0.2, b=0.1-0.5, c=0-0.2, d=0.01-0.5, e=0-0.6, a+b+c+d+e=1.0, at least one phenyl group is included in the molecule. A film of the silicone resin has a refractive index of at least 1.48.

## Claims

### Claim 1

A method for preparing a silicone resin represented by the compositional formula (1) and has a weight average molecular weight of 1,000 to 8,000,
[(C6H5)3SiO1/2]a[R13SiO1/2]b[R22SiO2/2]c[R3SiO3/2]d[SiO4/2]e (1)
wherein R1 is a group, exclusive of phenyl, selected from among C1-C8 alkyl groups, C6-C12 aryl groups and C1-C8 fluorinated alkyl groups, R2 and R3 are each independently a group selected from among C1-C8 alkyl groups, C6-C12 aryl groups and C1-C8 fluorinated alkyl groups, a is a number of 0.01 to 0.2, b is a number of 0.1 to 0.5, c is a number of 0 to 0.2, d is a number of 0.01 to 0.5, e is a number of 0 to 0.6, a+b+c+d+e is equal to 1.0, R1 to R3 and a to e are selected such that at least one phenyl group is included in the molecule, and
a film of the silicone resin having a refractive index of at least 1.48;
the method comprising the following steps (i) and (ii):
(i) effecting hydrolytic condensation of at least one organosilicon compound selected from the general formulae (2) and (3) with at least one compound selected from silanes having the general formulae (4), (5) and (6) and partial hydrolytic condensates thereof in a solventless system or a solvent,
R13SiOSiR13 (2)
R13SiOH (3)
wherein R1 is as defined above,
(R4O)2SiR22 (4)
(R4O)3SiR3 (5)
(R4O)4Si (6)
wherein R2 and R3 are as defined above, R4 is each independently hydrogen or a substituted or unsubstituted monovalent hydrocarbon group; and
(ii) adding triphenylsilanol and a solvent to the hydrolytic condensate, and effecting condensation of the hydrolytic condensate with triphenylsilanol in the presence of a basic catalyst.

### Claim 2 (depends on 1)

The method of claim 1 wherein the basic catalyst is sodium hydrogencarbonate or sodium acetate.

### Claim 3 (depends on 1)

The method of claim 1, wherein the silicone resin has a phenyl content of at least 30% by weight.

### Claim 4 (depends on 1)

The method of claim 1, wherein R3 is phenyl.

### Claim 5 (depends on 1)

The method of claim 1, wherein c is 0 in formula (1), R1 is methyl, and R3 is phenyl.

### Claim 6 (depends on 1)

The method of claim 1, wherein the solvent in the step (i) comprises at least one selected from the group consisting of toluene, xylene, isoparaffin, tetrahydrofuran, methanol, ethanol, isopropyl alcohol, and butanol.