Co-modified organopolysiloxane, and powder treatment agent and powder composition comprising the same

Patent metadata

Field	Value
Publication number	US-9441009-B2
Application number	US-201314433195-A
Country	US
Kind code	B2
Filing date	Oct 2, 2013
Priority date	Oct 2, 2012
Publication date	Sep 13, 2016
Grant date	Sep 13, 2016

Abstract

A co-modified organopolysiloxane having a group having a siloxane dendron structure and a group containing a saccharide component (e.g. a sugar lactone amide alkyl group) is disclosed. The present invention also provides a method for producing the co-modified organopolysiloxane, as well as a surface treatment agent, a powder treatment agent, a powder composition, a powder-in-oil dispersion, a preparation for external use, and the like containing the co-modified organopolysiloxane.

First claim

The invention claimed is:

1. A co-modified organopolysiloxane having a group (L 1 ) having a siloxane dendron structure and a group (Q) containing a saccharide component of formula (1)
R 1 a R 2 b L 1 c Q d SiO (4-a-b-c-d)/2   (1)

wherein
each R 1 is independently a substituted or unsubstituted monovalent hydrocarbon group having from 1 to 30 carbon atoms, or a hydrogen atom;
each R 2 is independently a substituted or unsubstituted straight-chain or branched monovalent hydrocarbon group having from 6 to 30 carbon atoms, or a chainlike organosiloxane group of formula (2-1);

wherein each R 11 is independently a substituted or unsubstituted monovalent hydrocarbon group having from 1 to 30 carbon atoms, a hydroxyl group, or a hydrogen atom, with at least one of the R 11 moieties being the monovalent hydrocarbon group; t is a number in a range of 2 to 10; and r is a number in a range of 1 to 500; or of formula (2-2) below:

wherein R 11 and r are defined above; and
L 1 represents a silylalkyl group having a siloxane dendron structure of formula (3) when i=1;

wherein each R 3 independently represents a substituted or unsubstituted, straight or branched monovalent hydrocarbon group having from 1 to 30 carbon atoms; R 4 each independently represents an alkyl group having from 1 to 6 carbon atoms or phenyl group; Z represents a divalent organic group; i represents a generation of the aforementioned silylalkyl group represented by L i and is an integer of 1 to k when k is a number of generations that is a number of repetitions of the silylalkyl group; the number of generations k is an integer from 1 to 10; L i+1 is the silylalkyl group when i is less than k, and R 4 when i=k, and h i is a number in a range from 0 to 3;
Q is a group containing a saccharide component of formula X-(G 1 ) n -(G 2 ) m , wherein G 1 is a saccharide component having from 5 to 12 carbon atoms; n+m is from 1 to 10; and n or m may be 0, G 2 is a saccharide component having from 5 to 12 carbon atoms which may be additionally substituted with an organic or organic silicon group;
X is a linking group independently selected from the following linking groups:
—R 5 —NHC(O)—R 6 —;
—R 5 —NHC(O)O—R 6 —;
—R 5 —NH—C(O)—NH—R 6 —;
—R 5 —O—R 6 —;
—R 5 —CH(OH)—CH 2 —O—R 6 —;
—R 5 —S—R 6 —;
—R 5 —CH(OH)—CH 2 —NH—R 6 —; and
—R 5 —N(R 1 )—R 6 —;

wherein R 5 and R 6 are divalent spacer groups containing (R a ) u , (R b ) v , and (R c ) x , where at least one of u, v, and x must be 1; R a and R c are alkylene groups having from 1 to 12 carbon atoms or polyoxyalkylene groups of formula (R d O) p , where R d is H or has from 1 to 12 carbon atoms; p is any integer from 1 to 50; each (R d O) moiety may be the same or different; R b is —N(R e )—, where R e is H, an alkyl group having from 1 to 12 carbon atoms, or X—Y, where X is as defined above or R 5 , and Y is a carboxylic acid, phosphate, sulfate, sulfonate, or tertiary ammonium group; 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.

2. The co-modified organopolysiloxane of claim 1 , wherein Q is a group containing a saccharide component obtained by a reaction between an amino group and a hydroxy functional saccharide.

3. The co-modified organopolysiloxane of claim 1 , wherein Q is a sugar lactone amide alkyl group obtained by a reaction between a silicon-bonded amino group of formula:
—R 12 —(N(R 13 )—R 14 ) w —NR 15 R 16

wherein
R 12 is an alkylene group having from 2 to 8 carbon atoms;
R 13 , R 15 , and R 16 are independently hydrogen atoms or monovalent organic groups having from 1 to 10 carbon atoms, but at least one of all of R 13 , R 15 , and R 16 is a hydrogen atom;
R 14 is an alkylene group having from 1 to 4 carbon atoms; and w is a number in a range of 0≦w≦6 and

a sugar lactone compound.

4. The co-modified organopolysiloxane of claim 1 , being of formula (1-1)

where R 1 , R 2 , L 1 and Q are defined above, and R is a group selected from R 1 , R 2 , L 1 , and Q; however, when n3=0, at least one R is L 1 ; and when n4=0, at least one R is Q; and (n1+n2+n3+n4) is a number in a range from 0 to 50; n1 is a number in a range from 0 to 45, n2 is a number in a range from 0 to 30, n3 is a number in a range from 0 to 20, and n4 is a number in a range from 0 to 2.

5. The co-modified organopolysiloxane of claim 1 , being of formula (1-1-1)

where R 1 , R 2 , L 1 , and Q defined above, (n1+n2+n3+n4) is a number in a range from 2 to 50, n1 is a number in a range from 0 to 45, 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.

6. The co-modified organopolysiloxane of claim 4 , wherein
in formula (1-1), L 1 is a functional group of formula (2-1) or formula (2-2):

wherein R 1 , R 2 , and Z defined above, and a 1 and a 2 are each independently numbers in a range of 0 to 3;
Q is a sugar lactone amide alkyl group (Q 1 ) obtained by a reaction between a silicon-bonded amino group of formula:
—R 12 —(N(R 13 )—R 14 ) w —NR 15 R 16

wherein R 12 is an alkylene group having from 2 to 8 carbon atoms;

R 13 , R 15 , and R 16 are independently hydrogen atoms or monovalent organic groups having from 1 to 10 carbon atoms, but at least one of R 13 , R 15 , and R 16 is a hydrogen atom;
R 14 is an alkylene group having from 1 to 4 carbon atoms; and
w is a number in a range of 0≦w≦6 and

a sugar lactone compound.

7. The co-modified organopolysiloxane of claim 6 , being of formula (1-1-A) or formula (1-1-B)

where Z, R 1 , R 2 , and Q 1 are defined above; R is a group selected from R 1 , R 2 , and L 1 and Q 1 ; (n1+n2+n3+n4) is a number in a range from 2 to 50; n1 is a number in a range from 0 to 45, 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.

8. A method for producing the co-modified organopolysiloxane of claim 1 , the method comprising the following steps (I) to (III):
step (I): producing a co-modified organopolysiloxane intermediate having a functional group that can react with a compound having a saccharide component directly or after a deprotection reaction by co-hydrosilylating: a compound having a siloxane dendron structure;

a compound having a functional group that can react with a compound having a saccharide component directly or after a deprotection reaction; and an organohydrogenpolysiloxane;
step (II): producing a co-modified organopolysiloxane intermediate having a functional group that can react with a compound having a saccharide component by performing a deprotection reaction as necessary on the co-modified organopolysiloxane intermediate obtained in step (I); and
step (III): reacting the co-modified organopolysiloxane intermediate obtained in step (I) or step (II) and a compound having a saccharide component to produce the co-modified organopolysiloxan

Assignees

• Dow Corning Toray Co Ltd

Inventors

• Furukawa Haruhiko
• Hayashi Akito
• Iimura Tomohiro

Classifications

• C08G77/38

  Polysiloxanes modified by chemical after-treatment · CPC title

• A61K2800/10

  General cosmetic use · CPC title

• A61Q1/08

  for cheeks, e.g. rouge · CPC title

• A61K8/898 Primary

  containing nitrogen, e.g. amodimethicone, trimethyl silyl amodimethicone or dimethicone propyl PG-betaine · CPC title

• A61Q1/02

  Preparations containing skin colorants, e.g. pigments (preparations in powder form A61Q1/12) · CPC title