# US 8,784,787 B2 · Co-modified organopolysiloxane

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- Number: US 8,784,787 B2
- Document ID: US8784787B2
- Status: Granted
- Kind: B2
- Application number: 13/503,455
- Filed: 2010-10-25
- Published: 2012-10-25
- Granted: 2014-07-22
- Earliest claimed: 2009-10-23
- Assignees: Dow Corning Toray Co., Ltd.
- Applicants: Seiki Tamura; Tomohiro Iimura; Akito Hayashi; Tatsuo Souda; Haruhiko Furukawa
- Inventors: Seiki Tamura; Tomohiro Iimura; Akito Hayashi; Tatsuo Souda; Haruhiko Furukawa
- Web page: https://patentgrep.com/patent/US8784787B2

## CPC

- C09C 3/12: Treatment with organosilicon compounds {(C09C3/006 takes precedence)}
- A61K 8/022: {Powders; Compacted Powders}
- A61K 8/044: {Suspensions}
- A61K 8/06: Emulsions
- A61K 8/894: modified by a polyoxyalkylene group, e.g. cetyl dimethicone copolyol
- A61Q 19/00: Preparations for care of the skin
- C08G 77/38: Polysiloxanes modified by chemical after-treatment
- C08G 77/46: containing polyether sequences
- C08G 77/50: by carbon linkages
- C08L 83/16: in which all the silicon atoms are connected by linkages other than oxygen atoms
- C09C 1/3081: {Treatment with organo-silicon compounds}
- A61K 2800/10: General cosmetic use
- A61Q 1/02: Preparations containing skin colorants, e.g. pigments (preparations in powder form A61Q1/12)
- A61Q 1/04: for lips
- A61Q 1/08: for cheeks, e.g. rouge
- A61Q 1/10: for eyes, e.g. eyeliner, mascara
- A61Q 1/12: Face or body powders for grooming, adorning or absorbing
- 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
- C09C: TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES (treatment of materials specially adapted to enhance their filling properties in mortars, concrete or artificial stone C04B14/00, C04B18/00, C04B20/00); PREPARATION OF CARBON BLACK {; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS}
- 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)

## Abstract

A novel organopolysiloxane having a hydrophilic group, which can be produced easily and is not susceptible to two-phase separation, sedimentation of unreacted materials or the like after production, while being chemically stable and excellently practical, is disclosed. A method for producing the organopolysiloxane; and uses of the organopolysiloxane are also disclosed. The organopolysiloxane is a co-modified organopolysiloxane which has a group having a siloxane dendron structure and a hydrophilic group.

## Claims

### Claim 1

A co-modified organopolysiloxane having a group with a siloxane dendron structure and a hydrophilic group, expressed by the following general formula (1);
General Formula (1):
R1aL1bQcSiO(4−a−b−c)/2 (1)
wherein,
R1 is a monovalent organic group with the exception of groups corresponding to L1 or Q, or a hydrogen atom;
L1 is a silylalkyl group having a siloxane dendron structure expressed by the following general formula (2) when i=1;
wherein, R1 is synonymous with the group described above, R2 is a phenyl group or an alkyl group having from 1 to 6 carbons, 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; ai is a number in a range of 0 to 3;
Q is a hydrophilic group derived from a hydrophilic compound selected from polyhydric alcohols comprising glycerin or polyglycerines, said hydrophilic group bonded to the silicon atom via a linking group that is at least divalent, and comprises at least one hydrophilic unit selected from hydrophilic units expressed by the following structural formulae (3-2) to (3-4):
wherein W is a hydrogen atom or an alkyl group having from 1 to 20 carbons;
wherein W is synonymous with the group described above; and
wherein a, b, and c are in a range so that 1.0≦a≦2.5, 0.001≦b≦1.5, and 0.001≦c≦1.5.

### Claim 2 (depends on 1)

The co-modified organopolysiloxane according to claim 1, wherein in the general formula (1), L1 is a functional group expressed by the following general formula (2-1) or general formula (2-2):
wherein R1, R2, and Z are synonymous with the groups described above, and a1 and a2 are each independently numbers in a range of 0 to 3.

### Claim 3 (depends on 1)

The co-modified organopolysiloxane according to claim 1, expressed by structural formula (1-1) below,
wherein R1, L1, and Q are groups that are synonymous with those described above, R is a group selected from R1, L1, and Q; however, when n2=0, at least one R is L1; and when n3=0, at least one R is Q; (n1+n2+n3) is a number in a range from 3 to 2,000; and n1, n2, and n3 are numbers in a range from 0 to 2,000.

### Claim 4 (depends on 1)

The co-modified organopolysiloxane according to claim 1, expressed by structural formula (1-1-1) or (1-1-2) below,
wherein Z and R1 are groups that are synonymous with those described above; R is a group selected from R1, the L1, and Q1, described hereinafter; n1 is a number in a range from 10 to 1,000; n2 is a number in a range from 0 to 250; n3 is a number in a range from 0 to 250; however, when n2=0, at least one R is L1; and when n3=0, at least one R is Q1;
Q1 are each independently a hydrophilic group selected from the group consisting of structural formulae (4-1-2), (4-2-2), (4-3-2), and (4-4-2) below:
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 (3-2) to (3-4) 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.

### Claim 5 (depends on 4)

The co-modified organopolysiloxane according to claim 4, wherein in the structural formula (1-1-1) or (1-1-2), Z are each independently a group selected from divalent organic groups expressed by general formulae (5-1) to (5-7) below:
wherein, R6 may have a substituent, and are each independently a straight or branched chain alkylene group or alkenylene group having from 2 to 22 carbons, or an arylene group having from 6 to 22 carbons; and R7 is a group selected from divalent organic groups expressed by the following formulae:

### Claim 6 (depends on 4)

The co-modified organopolysiloxane according to claim 4, wherein in the structural formulae (4-1-2), (4-2-2), (4-3-2), and (4-4-2), p is 1 and R3 is a group selected from divalent organic groups expressed by general formula (5-1), (5-1-2), (5-1-3), or (5-2) below:
wherein, R6 may have a substituent, and are each independently a straight or branched chain alkylene group or alkenylene group having from 2 to 22 carbons, or an arylene group having from 6 to 22 carbons.

### Claim 7 (depends on 1)

A surfactant comprising the co-modified organopolysiloxane described in claim 1.

### Claim 8 (depends on 1)

An emulsion composition comprising: (A) the co-modified organopolysiloxane described in claim 1, (B) water, and (C) at least one oil agent selected from silicone oil, hydrocarbon oil, or ester oil that is a liquid at from 5 to 100° C.

### Claim 9 (depends on 8)

A method of adjusting transparency of the emulsion composition described in claim 8, comprising independently mixing an aqueous phase including the component (B) and an oil phase including the component (A) and the component (C) and, thereafter, adjusting a difference between refractive indexes at 25° C. of both phases so as to be less than or equal to 0.0020 units, and emulsifying.

### Claim 10 (depends on 1)

A powder treatment agent comprising the co-modified organopolysiloxane described in claim 1.

### Claim 11 (depends on 1)

A powder composition comprising: (A) the co-modified organopolysiloxane described in claim 1, and (D) a powder or a powdered colorant.

### Claim 12 (depends on 11)

The powder composition according to claim 11, wherein the component (D) is one or two or more selected from the group consisting of an inorganic pigment powder, an organic pigment powder, and a resin powder, having an average diameter in a range of 1 nm to 20 μm.

### Claim 13 (depends on 1)

A powder in oil dispersion comprising: (A) the co-modified organopolysiloxane described in claim 1, (D) a powder or a powdered colorant, and (C) at least one oil agent selected from a silicone oil, a nonpolar organic compound, or a low polarity organic compound, that is a liquid at from 5 to 100° C.

### Claim 14 (depends on 1)

A topical composition comprising the co-modified organopolysiloxane described in claim 1.

### Claim 15 (depends on 8)

A cosmetic composition comprising the emulsion composition described in claim 8.

### Claim 16 (depends on 11)

A cosmetic composition comprising the powder composition described in claim 11.

### Claim 17 (depends on 13)

A cosmetic composition comprising the powder in oil dispersion described in claim 13.

### Claim 18 (depends on 1)

A substantially water-free cosmetic composition comprising: the co-modified organopolysiloxane described in claim 1, and an oil agent.

### Claim 19 (depends on 14)

The topical composition according to claim 14 as a cosmetic composition, further comprising: at least one selected from the group consisting of (E) a polyhydric alcohol or a lower monohydric alcohol, (F) an inorganic salt or an organic salt, and (G) a silicone-based surfactant different than the co-modified organopolysiloxane component (A).

### Claim 20 (depends on 14)

The topical composition according to claim 14 as a cosmetic composition, further comprising: (H) at least one selected from the group consisting of a crosslinking organopolysiloxane, an organopolysiloxane elastomer spherical powder, a silicone resin, an acryl silicone dendrimer copolymer, a silicone raw rubber, a polyamide-modified silicone, an alkyl-modified silicone wax, and an alkyl-modified silicone resin wax.

### Claim 21 (depends on 14)

The topical composition according to claim 14 as a cosmetic composition, further comprising: (J) one or two or more selected from the group consisting of an anionic surfactant, a cationic surfactant, a nonionic surfactant with the exception of silicone-based surfactants, an amphoteric surfactant, and a semipolar surfactant.

### Claim 22 (depends on 14)

The topical composition according to claim 14 as a cosmetic composition, further comprising: (K) a water-soluble polymer or (L) an ultraviolet light blocking component.

### Claim 23 (depends on 1)

A method of manufacturing the co-modified organopolysiloxane described in claim 1, wherein the co-modified organopolysiloxane is obtained by reacting at least: (a) an organohydrogensiloxane expressed by general formula (1′) below:
R1aHb+cSiO(4−a−b−c)/2 (1′)
wherein R1, a, b, and c are the same as described above; (b) a hydrophilic derivative having one reactive unsaturated group in the molecule; and (c) a siloxane dendron having one reactive unsaturated group in the molecule; in the presence of a hydrosilylation reaction catalyst.

### Claim 24 (depends on 23)

The method of manufacturing a co-modified organopolysiloxane according to claim 23, wherein (b) the hydrophilic derivative having one reactive unsaturated group in the molecule, (c) the siloxane dendron having one reactive unsaturated group in the molecule, and (a) the organohydrogensiloxane expressed by the general formula (1′) are reacted together, while the component (b) and the component (c) are at least in a state of coexistence.

### Claim 25 (depends on 23)

The method of manufacturing a co-modified organopolysiloxane according to claim 23, wherein: (c) the siloxane dendron having one reactive unsaturated group in the molecule is a compound expressed by general formula (2′) below that has a siloxane dendron structure having one carbon-carbon double bond at a molecular terminal:
wherein, R1 is a group that is synonymous with that described above, L′1 is a methyl group or, when j=1, is a silylalkyl group expressed by general formula (2″) below, and Z′ is a divalent organic group;
wherein, R1 is synonymous with the group described above, R2 is a phenyl group or an alkyl group having from 1 to 6 carbons, and Z is a divalent organic group; j represents a generation of the silylalkyl group represented by Lj 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 j is less than c′ and is a methyl group or a phenyl group when j=c′; and aj is a number in a range of 0 to 3.