# US 2014/0371330 A1 · Novel Co-Modified Organopolysiloxane, And Treatment Agent And External Use Preparation Comprising The Same

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- Number: US 2014/0371330 A1
- Document ID: US20140371330A1
- Status: Published application
- Kind: A1
- Application number: 14/369,247
- Filed: 2012-12-26
- Published: 2014-12-18
- Earliest claimed: 2011-12-27
- Assignees: Dow Corning Toray Co., Ltd.
- Applicants: Dow Corning Toray Co., Ltd.
- Inventors: Akito Hayashi; Tomohiro Iimura; Tatsuo Souda; Seiki Tamura; Haruhiko Furukawa
- Web page: https://patentgrep.com/patent/US20140371330A1

## CPC

- C08G 77/18: to alkoxy or aryloxy groups
- A61K 8/022: {Powders; Compacted Powders}
- A61K 8/064: {Water-in-oil emulsions, e.g. Water-in-silicone emulsions}
- A61K 8/894: modified by a polyoxyalkylene group, e.g. cetyl dimethicone copolyol
- A61Q 1/00: Make-up preparations; Body powders; Preparations for removing make-up
- A61Q 1/02: Preparations containing skin colorants, e.g. pigments (preparations in powder form A61Q1/12)
- C08G 77/38: Polysiloxanes modified by chemical after-treatment
- C08G 77/46: containing polyether sequences
- C08G 77/50: by carbon linkages
- A61K 2800/10: General cosmetic use
- A61Q 1/04: for lips
- A61Q 1/06: Lipsticks
- A61Q 1/10: for eyes, e.g. eyeliner, mascara
- 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
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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

## Abstract

A co-modified organopolysiloxane having a viscosity at 25° C. of not more than 1,500 mPa·s, a group that has a siloxane dendron structure, a hydrophilic group, and expressed by the following general formula (1): R1aR2bL1cQdSiO(4-a-b-c-d)/2 (1). The invention also relates to a powder treatment agent, a powder in oil dispersion, an external use preparation (particularly a cosmetic composition) composition comprising the co-modified organopolysiloxane. In said general formula (1), R1 is a monovalent hydrocarbon group or a hydrogen atom; R2 is a monovalent hydrocarbon group having from 6 to 30 carbons; L1 is a silylalkyl group having a siloxane dendron structure; and Q is a hydrophilic segment.

## Claims

### Claim 1

A co-modified organopolysiloxane having a viscosity at 25° C. of not more than 1,500 mPa·s, a group that has a siloxane dendron structure, a hydrophilic group, and expressed by the following general formula (1):
R1aR2bL1cQdSiO(4-a-b-c-d)/2 (1)
wherein,
R1 is a substituted or unsubstituted monovalent hydrocarbon group having from 1 to 30 carbons, or a hydrogen atom;
R2 is a substituted or unsubstituted straight or branched monovalent hydrocarbon group having from 6 to 30 carbons; L1 is a silylalkyl group having a siloxane dendron structure expressed by the following general formula (2) when i=1; and Q is a hydrophilic segment, wherein General Formula (2) is represented by:
wherein, R1 is as defined above, RC is an alkyl group having 1 to 6 carbons or a phenyl group, and Z is a divalent organic group; i represents a generation of the silylalkyl group represented by Li, and is an integer of 1 to c when c is a number of generations that is a number of repetitions of the silylalkyl group; the number of generations c is an integer from 1 to 10, and Li+1 is the silylalkyl group when i is less than c and is a methyl group or a phenyl group when i=c; and ai is a number in a range of 0 to 3; and a, b, c, and d are numbers in ranges so that 1.0≦a+b≦2.5, 0.001≦c≦1.5, and 0.001≦d≦1.5.

### Claim 2 (depends on 1)

The co-modified organopolysiloxane according to claim 1, wherein an HLB value calculated by formula (A) below is not more than 2.0:
HLB=(total molecular weight of hydrophilic group moiety/total molecular weight)×20 formula (A).

### Claim 3 (depends on 1)

The co-modified organopolysiloxane according to claim 1, that is represented by structural formula (1-1) below:
wherein R1, R2, L1 and Q are as defined above, and R is a group selected from R1, R2, L1, and Q; however, when n3=0, at least one R is L1; and when n4=0, at least one R is Q; and (n1+n2+n3+n4) is a number in a range from 2 to 80; n1 is a number in a range from 0 to 70, n2 is a number in a range from 0 to 30, n3 is a number in a range from 1 to 20, and n4 is a number in a range from 0.1 to 2.

### Claim 4 (depends on 1)

The co-modified organopolysiloxane according to claim 1, that is represented by structural formula (1-1-1) below:
wherein R1, R2, L1, and Q are as defined above, (n1+n2+n3+n4) is a number in a range from 2 to 80, n1 is a number in a range from 0 to 70, n2 is a number in a range from 0 to 30, n3 is a number in a range from 1 to 20, and n4 is a number in a range from 0.1 to 2.

### Claim 5 (depends on 1)

The co-modified organopolysiloxane according to claim 1, wherein in the formulae (1) to (1-1-1), L1 is a functional group expressed by general formula (2-1) or general formula (2-2) below:
wherein R1, RC, and Z are as defined above, and a1 and a2 are each independently numbers in a range of 0 to 3.

### Claim 6 (depends on 1)

The co-modified organopolysiloxane according to claim 1, wherein in the formulae (1), Q is: a hydrophilic group that is bonded to the silicon atom via a linking group that is at least divalent, comprising a sugar alcohol represented by structural formulae (3-1) and (3-2) below, or a hydrophilic group that is bonded to the silicon atom via a linking group that is at least divalent, comprising at least one hydrophilic unit selected from hydrophilic units represented by structural formulae (3-3) to (3-6) below:
Structural formulae (3-1) and (3-2):
wherein Z is a divalent organic group, and m is 1 or 2;
wherein Z is as defined above, and m′ is 0 or 1;
Structural formulae (3-3) to (3-6):
—CrH2r—O— (3-3)
wherein r is a number in a range of 1 to 6;
wherein W is a hydrogen atom or an alkyl group having from 1 to 20 carbons;
wherein W is as defined above; and

### Claim 7 (depends on 6)

The co-modified organopolysiloxane according to claim 6, wherein in the general formulae (1), Q is a hydrophilic segment bonded to the silicon atom via a linking group that is at least divalent, comprising at least one linearly bonded hydrophilic unit selected from hydrophilic units represented by structural formulae (3-3) to (3-6); or Q is a hydrophilic group bonded to the silicon atom via a linking group that is at least divalent, comprising not less than two of at least one hydrophilic unit selected from hydrophilic units represented by structural formulae (3-3) to (3-6), and a branch unit selected from groups represented by structural formulae (3-7) to (3-9) below:

### Claim 8 (depends on 6)

The co-modified organopolysiloxane according to claim 6, wherein in the general formulae (1), Q is a hydrophilic segment expressed by general formulae (4-1) to (4-4) below:
General Formula (4-1):
—R3(—O—X1m—R4)p (4-1)
wherein, R3 is an organic group having (p+1) valency, and p is a number that is greater than or equal to 1 and less than or equal to 3; X1 are each independently at least one hydrophilic unit selected from the hydrophilic units expressed by the general formulae (3-3) to (3-6) above, and m is a number in a range of 1 to 100; and R4 is a hydrogen atom or a group selected from the group consisting of glycidyl groups, acyl groups, and alkyl groups having from 1 to 20 carbons;
General Formula (4-2):
—R3(—O—X2)p (4-2)
wherein, R3 is as defined above, p is as defined above; and X2 is a hydrophilic group represented by structural formula (4-2-1) below;
wherein, the at least one hydrophilic unit selected from the hydrophilic units expressed by the general formulae (3-3) to (3-6) is bonded to two oxygen atoms, each independently;
General Formula (4-3):
—R3(—O—X3)p (4-3)
wherein R3 is as defined above, p is as defined above; and X3 is a hydrophilic group represented by structural formula (4-3-1) below:
wherein, the at least one hydrophilic unit selected from the hydrophilic units expressed by the general formulae (3-3) to (3-6) is bonded to two oxygen atoms, each independently;
General Formula (4-4):
—R3(—O—X4)p (4-4)
wherein R3 is as defined above, p is as defined above; and X4 is a hydrophilic group represented by structural formula (4-4-1) below:
wherein, the at least one hydrophilic unit selected from the hydrophilic units expressed by the general formulae (3-3) to (3-6) is bonded to two oxygen atoms, each independently.

### Claim 9 (depends on 6)

The co-modified organopolysiloxane according to claim 6, that is represented by structural formula (1-1-A) or (1-1-B) below.
wherein Z, R1, and R2 are as defined above; R is a group selected from the R1, R2, and L1 moieties, or Q1; (n1+n2+n3+n4) is a number in a range from 0 to 80; n1 is a number in a range from 0 to 70, n2 is a number in a range from 0 to 30, n3 is a number in a range from 1 to 20, and n4 is a number in a range from 0.1 to 2; Q1 are each independently a hydrophilic group selected from the group consisting of structural formulae (3′-1), (3′-2), (4-1-2), (4-2-2), (4-3-2), and (4-4-2) below:
wherein Z1 is a substituted or unsubstituted straight or branched alkylene group having from 3 to 5 carbons, and m is 1 or 2;
wherein R3 is an organic group having (p+1) valency, and p is a number that is greater than or equal to 1 and less than or equal 3; X1 are each independently at least one hydrophilic unit selected from the hydrophilic units expressed by the general formulae (3-3) to (3-6), and m is a number in a range of 1 to 100; and R4 is a hydrogen atom or a group selected from the group consisting of glycidyl groups, acyl groups, and alkyl groups having from 1 to 20 carbons.

### Claim 10 (depends on 1)

A surfactant or a surface treatment agent comprising the co-modified organopolysiloxane according to claim 1.

### Claim 11 (depends on 1)

A powder treatment agent comprising the co-modified organopolysiloxane according to claim 1.

### Claim 12 (depends on 1)

A powder composition comprising:
(A) the co-modified organopolysiloxane according to claim 1, and
(B) a powder or coloring agent.

### Claim 13 (depends on 12)

The powder composition according to claim 12, wherein the component (B) is one or two or more selected from the group consisting of an inorganic pigment powder, an organic pigment powder, and a resin powder, and has an average diameter in a range of 1 nm to 20 μm.

### Claim 14 (depends on 1)

A powder in oil dispersion comprising: (A) the co-modified organopolysiloxane according to claim 1, (B) a powder or coloring agent, and (C) one or more oil agent selected from a silicone oil, a nonpolar organic compound, and a low polarity organic compound that is liquid from 5° C. to 100° C.

### Claim 15 (depends on 1)

A preparation for external use comprising the co-modified organopolysiloxane according to claim 1.

### Claim 16 (depends on 15)

The preparation for external use according to claim 15 wherein the preparation is a cosmetic composition or a medicament.

### Claim 17 (depends on 12)

A cosmetic composition comprising the powder composition described in claim 12.

### Claim 18 (depends on 14)

A cosmetic composition comprising the powder in oil dispersion according to claim 14.

### Claim 19 (depends on 1)

A make-up cosmetic composition comprising:
(A) the co-modified organopolysiloxane according to claim 1;
(B) a powder or coloring agent; and
(C) a silicone oil, a nonpolar organic compound, or a low polarity organic compound that is liquid from 5° C. to 100° C.