Saccharide siloxane copolymers and methods for their preparation and use

Patent metadata

Field	Value
Publication number	US-9192564-B2
Application number	US-201113817634-A
Country	US
Kind code	B2
Filing date	Aug 15, 2011
Priority date	Aug 23, 2010
Publication date	Nov 24, 2015
Grant date	Nov 24, 2015

Abstract

A novel saccharide siloxane copolymer is useful in personal care compositions. The saccharide siloxane copolymer may be used as a universal emulsifier to prepare low odor emulsions for personal care applications.

First claim

The invention claimed is:

1. A saccharide siloxane copolymer of formula:
R 2 a R 1′ a′ R 1 (3-a-a′) SiO—[(SiR 2 R 1 O) m —(SiR 1 2 O) n (SiR 1′ R 1 O) o ] y —SiR 1 (3-a-a′) R 1′ a′ R 2 a ;

where
each R 1 can be the same or different and each R 1 comprises hydrogen, an alkyl group of
1 to 12 carbon atoms, an organic group, or a group of formula R 3 -Q;
Q comprises an epoxy, cycloalkylepoxy, primary or secondary amino, ethylenediamine, carboxy, halogen, vinyl, allyl, anhydride, or mercapto functionality;

each R 1′ is a monovalent organic group with an average of at least 16 carbon atoms;
subscript m has an average value ranging from 0 to 10,000;
subscript n has an average value ranging from 0 to 10,000;
subscripts m, n, and o may be the same or different;
subscript o has an average value ranging from 0 to 10,000;
each subscript a is independently 0, 1, 2, or 3;
each subscript a′ is independently 0, 1, 2, or 3;
subscript y is an integer such that the copolymer has a molecular weight less than 1 million, and subscript y has a value of at least 1; provided when each subscript a′ is 0, then subscript o is greater than 0;
each R 2 has formula Z-(G 1 ) b -(G 2 ) c , and there is an average of at least one R 2 per copolymer molecule, where
G 1 is a saccharide component comprising 5 to 12 carbon atoms,
a quantity (b+c) has a value ranging from 1 to 10, and
subscript b or subscript c can be 0,
G 2 is a saccharide component comprising 5 to 12 carbon atoms additionally substituted with organic or organosilicon radicals, each Z is a linking group and is independently selected from the group consisting of:
—R 3 —NHC(O)—R 4 —;
—R 3 —NHC(O)O—R 4 —;
—R 3 —NH—C(O)—NH—R 4 —;
—R 3 —C(O)—O—R 4 —;
—R 3 —O—R 4 —;
—R 3 —CH(OH)—CH 2 —O—R 4 —;
—R 3 —S—R 4 —;
—R 3 —CH(OH)—CH 2 —NH—R 4 —;
—R 3 —N(R 1 )—R 4 —;
—NHC(O)—R 4 —;
—NHC(O)O—R 4 —;
—NH—C(O)—NH—R 4 —;
—C(O)—O—R 4 —;
—O—R 4 —;
—CH(OH)—CH 2 —O—R 4 —;
—S—R 4 —;
—CH(OH)—CH 2 —NH—R 4 —;
—N(R 1 )—R 4 —;
—R 3 —NHC(O)—;
—R 3 —NHC(O)O—;
—R 3 —NH—C(O)—NH—;
—R 3 —C(O)—O—;
—R 3 —O—;
—R 3 —CH(OH)—CH 2 —O—;
—R 3 —S—;
—R 3 —CH(OH)—CH 2 —NH—;
—R 3 —N(R 1 )—;
—R 3 —N(R 8 )—C(O)—R 4 —,
—R 3 —CH(OH)—CH 2 —N(R 8 )—R 4 —, or
—R 3 —CH(N(R 4 )(R 8 ))CH 2 OH;
where each R 3 and each R 4 are divalent spacer groups comprising a group of formula (R 5 ) r (R 6 ) s (R 7 ) t ,
 where at least one of subscripts r, s and t is 1, and
 each R 5 and each R 7 independently an alkylene group of 1 to 12 carbon atoms;
 each R 6 is —N(R 8 )—, where R 8 is selected from R 3 , a group of formula Z—X, a monovalent hydrocarbon group, or a reaction product of —N(H)— with an epoxy functional group, a cycloalkylepoxy functional group, a glycidyl ether functional group, an acidic anhydride functional group, or a lactone;
 each X is independently a divalent carboxylic acid, phosphate, sulfate, sulfonate or quaternary ammonium radical, and
with the provisos that
 at least one of R 3 and R 4 must be present in the linking group, and
 each R 3 and each R 4 may be the same or different.

2. The copolymer of claim 1 , where each Z is independently selected from the group consisting of: —R 3 —N(R 8 )—C(O)—R 4 —, —R 3 —CH(OH)—CH 2 —N(R 8 )—R 4 —, or —R 3 —CH(N(R 4 )(R 8 ))CH 2 OH.

3. The copolymer of claim 1 , where subscripts m and n are integers from 0 to 500 and may be the same or different.

4. The copolymer of claim 1 , where subscript o is an integer from 0 to 2,500.

5. The copolymer of claim 1 wherein R1′ is an alkyl group with an average of at least 16 carbon atoms.

6. The copolymer of claim 5 wherein R1′ is an alkyl group with an average of from 16 to 40 carbon atoms.

7. The compolymer of claim 1 wherein each Z is a linking group and is independently selected from the group consisting of:
—R 3 —NHC(O)—R 4 —;
—R 3 —NHC(O)O—R 4 —;
—R 3 —NH—C(O)—NH—R 4 —;
—R 3 —C(O)—O—R 4 —;
—R 3 —CH(OH)—CH 2 —O—R 4 —;
—R 3 —S—R 4 —;
—R 3 —CH(OH)—CH 2 —NH—R 4 —;
—R 3 —N(R 1 )—R 4 —;
—NHC(O)—R 4 —;
—NHC(O)O—R 4 —;
—NH—C(O)—NH—R 4 —;
—C(O)—O—R 4 —;
—CH(OH)—CH 2 —O—R 4 —;
—S—R 4 —;
—CH(OH)—CH 2 —NH—R 4 —;
—N(R 1 )—R 4 —;
—R 3 —NHC(O)—;
—R 3 —NHC(O)O—;
—R 3 —NH—C(O)—NH—;
—R 3 —C(O)—O—;
—R 3 —O—;
—R 3 —CH(OH)—CH 2 —O—;
—R 3 —S—;
—R 3 —CH(OH)—CH 2 —NH—;
—R 3 —N(R 1 )—;
—R 3 —N(R 8 )—C(O)—R 4 —,
—R 3 —CH(OH)—CH 2 —N(R 8 )—R 4 —, or
—R 3 —CH(N(R 4 )(R 8 ))CH 2 OH.

8. A method for making a saccharide siloxane copolymer according to claim 1 , where the method comprises the steps of:
i) reacting an organofunctional polyorganosiloxane with a sugar moiety to produce the saccharide siloxane copolymer in the presence of a solvent;
optionally ii) removing a portion of the solvent; and
optionally iii) adding an oil.

9. The method of claim 8 , where the oil is added before and/or during step i).

10. The method of claim 8 where the oil is added during and/or after step ii).

11. The method of claim 8 , further comprising iv) removing the solvent.

12. The method of claim 8 , where step i) is performed by reacting ingredients comprising:
(A) an amino-functional polyorganosiloxane, and
(B) a sugar lactone.

13. The method of claim 8 , where step i) is performed by reacting ingredients comprising:
(A) an epoxy-functional polyorganosiloxane, and
(B) an n-alkyl glucamine.

14. The method of claim 8 , where step i) is performed by a method comprising:
1) reacting (a) an n-alkyl-glucamine with (b) an alkenyl functional epoxy compound, and
2) hydrosilylating the product of step 1) with (c) a polyorganohydrogensiloxane.

15. The method of claim 14 , where the product of step i) contains secondary amine functionality, further comprising a step of reacting the product of step i) with a capping agent selected from a lactone, a halogenated unsaturated compound, an epoxy functional compound, or an acid anhydride.

16. The method of claim 8 , where the solvent is present, and the solvent is an alcohol selected from methanol, ethanol, n-propanol, isopropanol, 2-propanol, isobutanol, n-butanol, and combinations thereof.

17. The method of claim 8 , where the oil is present, and the oil is a silicone oil.

18. The method of claim 17 , where the oil is a polydialkylsiloxane.

19. The method of claim 8 , where the oil is present, and the oil is an organic oil selected from a hydrocarbon oil, an ester, a vegetable oil, a mineral oil, or a fatty alcohol.

20. The method of claim 8 , where the copolymer and the oil are present in an amounts such that a weight ratio of copolymer/oil ranges from 1/1 to 1/50.

21. A method for making a copolymer according to claim 1 , comprising:
1) equilibration and/or condensation reaction of
i) a short chain silanol functional polyorganosiloxane,
ii) an aminodialkoxyalkylsilane,
iii) a dialkyldialkoxysilane, where at least one of the alkyl groups on the dialkyldialkoxysilane is R 1′ , and
iv) an endblocker; and

2) reaction of the product of step 1) with a sugar lactone.

22. The method of claim 21 , where the sugar lactone is an aldonolactone.

23. The method of claim 21 , further comprising step 3) reacting the product of step 2) with a capping agent selected from a lactone, a halogenated unsaturated compound, an epoxy functional compound, or an acid anhydride.

24. The method of claim 23 , where the lactone in step 3) is selected from: butyrolactone, epsilon caprolactone, gamm

Assignees

• Delvalle Cindy
• Joffre Eric Jude
• Scavuzzo Concettina
• Toth Simon
• Van Reeth Isabelle
• Dow Corning

Inventors

• Delvalle Cindy
• Joffre Eric Jude
• Scavuzzo Concettina
• Toth Simon
• Van Reeth Isabelle

Classifications

• A61Q19/00

  Preparations for care of the skin · CPC title

• A61K8/898 Primary

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

• A61K8/064

  Water-in-oil emulsions, e.g. Water-in-silicone emulsions · CPC title

• C08G77/388

  containing nitrogen · CPC title

• C08G77/42

  Block-or graft-polymers containing polysiloxane sequences (polymerising aliphatic unsaturated monomers on to a polysiloxane C08F283/12) · CPC title