# US 2014/0193353 A1 · Novel Organopolysiloxane Elastomer And Use Therefor

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- Number: US 2014/0193353 A1
- Document ID: US20140193353A1
- Status: Published application
- Kind: A1
- Application number: 14/122,688
- Filed: 2012-05-22
- Published: 2014-07-10
- Earliest claimed: 2011-05-30
- Assignees: Dow Corning Toray Co., Ltd.
- Inventors: Seiki Tamura; Tatsuo Souda; Chiichiro Hasegawa; Kazuhiko Kojima; Seiji Hori
- Web page: https://patentgrep.com/patent/US20140193353A1

## CPC

- A61K 8/892: modified by a hydroxy group, e.g. dimethiconol
- A61K 8/0241: {Containing particulates characterized by their shape and/or structure (see also A61K8/04, A61K8/11, and A61K8/14, further aspects are classified in A61K2800/40 and subcodes)}
- A61K 8/893: modified by an alkoxy or aryloxy group, e.g. behenoxy dimethicone or stearoxy dimethicone
- A61K 8/895: containing silicon bound to unsaturated aliphatic groups, e.g. vinyl dimethicone
- A61K 9/0014: {Skin, i.e. galenical aspects of topical compositions (non-active ingredients are additionally classified in A61K47/00; A61K9/0009, A61K9/0021, A61K9/7015, A61K9/7023 take precedence; cosmetic preparations A61K8/00, A61Q; preparations for wound dressings or bandages A61L26/00)}
- A61K 9/107: Emulsions {; Emulsion preconcentrates; Micelles (composition of emulsions A61K47/00)}
- A61K 47/34: Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers (A61K47/10 takes precedence)
- A61Q 5/00: Preparations for care of the hair
- A61Q 19/00: Preparations for care of the skin
- A61Q 19/007: {Preparations for dry skin}
- A61Q 19/08: Anti-ageing preparations
- C08G 77/46: containing polyether sequences
- C08G 77/50: by carbon linkages
- C08L 83/12: containing polyether sequences
- 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)
- A61K 2800/10: General cosmetic use
- C08G 77/12: containing silicon bound to hydrogen
- Y10T 428/2982: Particulate matter [e.g., sphere, flake, etc.]
- 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)
- A61Q: SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- 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)
- Y10T: TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION

## Abstract

The present invention relates to an organopolysiloxane elastomer having a silicon-bonded sugar alcohol-modified group and having a crosslinked three-dimensional network structure comprising a carbon-silicon bond in the crosslinking portion. The organomodified organopolysiloxane elastomer of the present invention has, for example, affinity with various oil agents, has excellent viscosity-improving characteristics, gelification characteristics, and emulsification characteristics, imparts excellent tactile sensation—in particular, an excellent tactile sensation characterized by smoothness with a velvet-like thickness—and imparts an excellent sensation during use.

## Claims

### Claim 1

An organopolysiloxane elastomer having a silicon-bonded sugar alcohol-modified group and having a crosslinked three-dimensional network structure comprising a carbon-silicon bond in a crosslinking portion of the crosslinked three-dimensional network structure.

### Claim 2 (depends on 1)

The organopolysiloxane elastomer according to claim 1, wherein the sugar alcohol-modified group is expressed by the following general formula (4-1):
wherein
R is a divalent organic group, and
e is 1 or 2, or the following general formula (4-2):
wherein
R is as defined above, and
e′ is 0 or 1.

### Claim 3 (depends on 1)

The organopolysiloxane elastomer according to claim 1, wherein in the general formula (4-1) or (4-2), the divalent organic group represented by R is a substituted or unsubstituted, straight-chain or branched divalent hydrocarbon group having from 3 to 5 carbon atoms.

### Claim 4 (depends on 1)

The organopolysiloxane elastomer according to claim 1 obtained by reacting: (A) an organohydrogenpolysiloxane;
(B) a sugar alcohol group-containing organic compound having a reactive unsaturated group; and
(C) at least one type of organic compound selected from the group consisting of (C1) an organic compound having an average number of reactive unsaturated groups in the molecule that is greater than 1 and (C2) an organic compound having at least one reactive unsaturated group and at least one epoxy group in the molecule.

### Claim 5 (depends on 4)

The organopolysiloxane elastomer according to claim 4, wherein an average value of a number of silicon-bonded hydrogen atoms per molecule of the component (A) reacting with the reactive unsaturated groups of the component (C) constituting the crosslinking portion is at least 1.5.

### Claim 6 (depends on 4)

The organopolysiloxane elastomer according to claim 4, wherein the component (A) is expressed by the average composition formula (1):
R1aHbSiO(4-a-b)/2 (1),
wherein R1 moieties are each independently monovalent organic groups, 1.0≦a≦3.0, and 0.001≦b≦1.5.

### Claim 7 (depends on 4)

The organopolysiloxane elastomer according to claim 4, wherein the component (C) is at least one type of organic compound selected from the following formulas (C1-1) to (C1-5) and (C2-1) to (C2-2):
(C1-1) an α,ω-diene expressed by the general formula (2-1):
CH2═CH(CH2)xCH═CH2 (2-1),
wherein 1≦x≦20;
(C1-2) an α,ω-diyne expressed by the general formula (2-2):
CH≡C(CH2)xC≡CH (2-2),
wherein 1≦x≦20;
(C1-3) an α,ω-ene-yne expressed by the general formula (2-3):
CH2═CH(CH2)xC≡CH (2-3),
wherein 1≦x≦20;
(C1-4) a bisalkenyl polyether compound expressed by the general formula (2-4):
CmH2m-1O(CnH2nO)yCmH2m-1 (2-4),
wherein 2≦m≦20, 2≦n≦4, y is the total value of the number of repetitions of the oxyethylene unit, the oxypropylene unit, or the oxybutylene unit, and 1≦y≦180;
(C1-5) an unsaturated group-containing silicone-compound expressed by the average composition formula (2-5):
R2pR3qSiO(4-p-q)/2 (2-5),
wherein R2 moieties may each be independent from one another but are monovalent organic groups that are different from R3;
R3 moieties are each independently monovalent unsaturated aliphatic hydrocarbon groups having from 2 to 30 carbon atoms, 1.0≦p≦2.5, and 0.001≦q≦1.5;
(C2-1) an unsaturated epoxy compound expressed by the general formula (2-6):
wherein R4 is a substituted or unsubstituted, straight-chain or branched monovalent hydrocarbon group having one reactive unsaturated group and from 2 to 20 carbon atoms; and
(C2-2) an unsaturated group-containing cycloaliphatic epoxy compound expressed by the general formula (2-7):
wherein R5 is a substituted or unsubstituted, straight-chain or branched monovalent hydrocarbon group having one reactive unsaturated group and from 2 to 20 carbon atoms;
R6 is a hydrogen atom or a methyl group; and
R7 is a hydrogen atom or a methyl group.

### Claim 8 (depends on 6)

The organopolysiloxane elastomer according to claim 6, wherein in the average composition formula (1), the monovalent organic group represented by R1 is selected from the following (D1) to (D10):
(D1) a substituted or unsubstituted, straight-chain or branched monovalent hydrocarbon group having from 1 to 60 carbon atoms;
(D2) a polyoxyalkylene group expressed by —R8O(AO)zR9, wherein AO is an oxyalkylene group having from 2 to 4 carbon atoms; R8 is a substituted or unsubstituted, straight-chain or branched divalent hydrocarbon group having from 3 to 5 carbon atoms; R9 is a hydrogen atom, a substituted or unsubstituted, straight-chain or branched monovalent hydrocarbon group having from 1 to 24 carbon atoms, or a substituted or unsubstituted, straight-chain or branched acyl group having from 2 to 24 carbon atoms; and z=1 to 100;
(D3) a substituted or unsubstituted, straight-chain or branched alkoxy group having from 1 to 30 carbon atoms;
(D4) a hydroxyl group;
(D5) an ester group expressed by —R10—COOR11, wherein R10 is a substituted or unsubstituted, straight-chain or branched divalent hydrocarbon group having from 2 to 20 carbon atoms, and R11 is a substituted or unsubstituted, straight-chain or branched monovalent hydrocarbon group having from 1 to 30 carbon atoms;
(D6) an ester group expressed by —R17—OCOR18, wherein R17 is a substituted or unsubstituted, straight-chain or branched divalent hydrocarbon group having from 2 to 20 carbon atoms, and R18 is a substituted or unsubstituted, straight-chain or branched monovalent hydrocarbon group having from 1 to 30 carbon atoms;
(D7) L1
where L1 is a silylalkyl group having a siloxane dendron structure and, when i=1, is expressed by the following general formula (3):
wherein
R12 is a substituted or unsubstituted, straight-chain or branched monovalent hydrocarbon group having from 1 to 30 carbon atoms;
R13 moieties each independently represents an alkyl group or a phenyl group having from 1 to 6 carbon atoms;
Z is a divalent organic group;
i represents a generation of the silylalkyl group represented by and is an integer of 1 to k when k is the number of generations, which is the number of repetitions of the silylalkyl group; the number of generations k is an integer from 1 to 10; is the silylalkyl group when i is less than k, and R13 when i=k; and h′ is a number in a range from 0 to 3;
(D8) an alkyl group substituted by a chain polysiloxane structure expressed by the following general formula (4):
wherein R14 moieties are each independently substituted or unsubstituted, straight-chain or branched monovalent hydrocarbon groups having from 1 to 30 carbon atoms, hydroxyl groups, or hydrogen atoms, and at least one of the R14 moieties is the monovalent hydrocarbon group; t is a number in a range from 2 to 10; and r is a number in a range from 1 to 100;
(D9) an epoxy group expressed by the following general formula (5):
wherein R15 is a substituted or unsubstituted, straight-chain or branched divalent hydrocarbon group having from 2 to 20 carbon atoms; and
(D10) a cycloaliphatic epoxy group expressed by the following general formula (6):
wherein R16 is a substituted or unsubstituted, straight-chain or branched divalent hydrocarbon group having from 2 to 20 carbon atoms, and R6 and R7 are synonymous with those described above.

### Claim 9 (depends on 1)

The organopolysiloxane elastomer according to claim 1 in a particulate form.

### Claim 10 (depends on 9)

The organopolysiloxane elastomer according to claim 9 in a particulate form having a volume average particle size in a range from 20 to 1000 μm.

### Claim 11 (depends on 1)

The organopolysiloxane elastomer according to claim 1, wherein the elastomer contains an oil agent in an amount greater than or equal to the weight of the elastomer itself and is swellable.

### Claim 12 (depends on 1)

A composition containing the organopolysiloxane elastomer according to claim 1 and at least one type of oil agent.

### Claim 13 (depends on 12)

The composition according to claim 12 in a paste form.

### Claim 14 (depends on 12)

The composition according to claim 12 obtained by mixing at least one type of oil agent after grinding the organopolysiloxane elastomer using a mechanical force or grinding a mixture of the organopolysiloxane elastomer and at least one type of oil agent using a mechanical force.

### Claim 15 (depends on 1)

An organopolysiloxane elastomer formed by treating the organopolysiloxane elastomer according to claim 1 with at least one type of acidic substance and removing volatile components by heating or decompression.

### Claim 16 (depends on 12)

The composition according to claim 12, the composition being an emulsion composition.

### Claim 17 (depends on 11)

A raw material for an external use preparation or a cosmetic composition containing the organopolysiloxane elastomer according to claim 11.

### Claim 18 (depends on 17)

The raw material for an external use preparation or a cosmetic composition according to claim 17, wherein the raw material is a thickening agent, a gelling agent, a tactile sensation improver, a surfactant, an emulsifier, or a powder dispersion stabilizer.

### Claim 19 (depends on 11)

An external use preparation containing the organopolysiloxane elastomer according to claim 11.

### Claim 20

A production method for an organopolysiloxane elastomer, comprising reacting: (A) an organohydrogenpolysiloxane;
(B) a sugar alcohol group-containing organic compound having a reactive unsaturated group; and
(C) at least one type of organic compound selected from the group consisting of (C1) an organic compound having an average number of reactive unsaturated groups in the molecule that is greater than 1 and (C2) an organic compound having at least one reactive unsaturated group and at least one epoxy group in the molecule.

### Claim 21 (depends on 20)

The production method for an organopolysiloxane elastomer according to claim 20, wherein part or all of the reaction requiring the component (A), the component (B) and the component (C) is performed in the presence of at least one solvent selected from a group indicated by (P-1) to (P-2):
(P-1): organic compound; and
(P-2): compound containing silicon atoms.

### Claim 22 (depends on 20)

The production method for an organopolysiloxane elastomer according to claim 20, wherein a crosslinking reaction is performed by adding the component (C) after first reacting the component (A) and the component (B); and an optional component (Q) that is a compound having one unsaturated group in the molecule, excluding the compound of (C2), is reacted with the component (A) prior to the reaction between the component (A) and the component (B), further reacted after the reaction between the component (A) and the component (B), or further reacted after crosslinking by the component (C).

### Claim 23 (depends on 20)

The production method for an organopolysiloxane elastomer according to claim 20, wherein a reaction between the component (A) and the component (C) is first performed to derive a crosslinked portion, and the component (B) is then added and reacted thereafter; and an optional component (Q) that is a compound having one unsaturated group in the molecule, excluding the compound of (C2), is reacted with the component (A) prior to the reaction between the component (A) and the component (C), further reacted after the reaction between the component (A) and the component (C), or further reacted after the reaction with the component (B).

### Claim 24 (depends on 20)

A production method for an organopolysiloxane elastomer, wherein after an organopolysiloxane elastomer obtained by the production method according to claim 20 or a composition containing the same is treated with at least one type of an acidic substance, volatile components are removed by heating or decompression.

### Claim 25 (depends on 24)

The production method for an organopolysiloxane elastomer according to claim 24, wherein after the elastomer is treated with the acidic substance, the elastomer is neutralized by adding at least one type of basic substance.