Saccharide siloxanes stable in aqueous environments and methods for the preparation and use of such saccharide siloxanes

1. A saccharide siloxane copolymer of formula:

R 2 a R 1 (3-a) SiO—[(SiR 2 R 1 O) m —(SiR 1 2 O) n ] y —SiR 1 (3-a) R 2 a ;

where each R 1 can be the same or different and each R 1 comprises hydrogen, an alkyl group, 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;

subscripts m and n are integers from 0 to 10,000 and may be the same or different;

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;

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 —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 are independently either an alkylene group of 1 to 12 carbon atoms or a group of formula (R 9 O) p , where

 subscript p is an integer with a value ranging from 1 to 50, and

 each R 9 is a divalent organic group, and

 each R 9 O may be the same or different,

each R 6 is —N(R 8 )—, where R 8 is selected from R 3 , a group of formula Z—X, an unsaturated hydrocarbon group, or a reaction product of —N(H)— with an epoxy functional group, a cycloalkylepoxy functional group, a glycidyl ether functional group, an acid 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 subscript y is greater than 0 and at least one of subscript m and subscript n is greater than 0.

3. The copolymer of claim 1 where each subscript a is 0 and each R 1 is an alkyl group of 1 to 12 carbon atoms.

4. A method for making a copolymer of claim 1 comprising:

1) reacting an amine functional polyorganosiloxane, containing a primary amine and a secondary amine, with a sugar lactone,

2) reacting the product of step 1) with a capping agent selected from a lactone, a halogenated unsaturated compound, an epoxy functional compound, or an acid anhydride.

5. The method of claim 4 , where the sugar lactone is an aldonolactone.

6. The method of claim 4 , where the lactone in step 2) is selected from: butyrolactone, epsilon caprolactone, gamma gluconolactone, delta gluconolactone, and lactobionolactone.

7. The method according to claim 4 , where the halogenated unsaturated compound is an alkenyl chloride.

8. The method according to claim 4 , where the epoxy functional compound is selected from allyl epoxy functional compounds, cycloalkylepoxy functional compounds, glycidyl ether functional compounds, and glycidol.

9. The method according to claim 4 , where the acid anhydride comprises acetic anhydride, chloroacetic anhydride, propionic anhydride, crotonic anhydride, methacrylic anhydride, butyric anhydride, isobutyric anhydride, diethyl pyrocarbonate, or 4-pentenoic anhydride.

10. A method for making a copolymer according to claim 1 comprising: 1) reacting an epoxy functional polyorganosiloxane with an n-alkyl glucamine.

11. The method of claim 10 , where the ingredients further comprise an alkene.

12. A method for making a copolymer according to claim 1 comprising: 1) reacting an n-alkyl-glucamine with an alkenyl functional epoxy compound, and 2) hydrosilylating the product of step 1) with a polyorganohydrogensiloxane.

13. The method of claim 12 , where the n-alkyl glucamine is n-methyl glucamine.

14. A composition comprising:

(A) the copolymer according to claim 1 and

(B) an additional ingredient.

15. The composition of claim 14 , where ingredient (B) comprises:

(ii) a carrier medium suitable to permit topical application composition to a portion of the body,

(iii) a cross-linker,

(iv) a surfactant, or

(v) a combination thereof.

16. The composition of claim 15 , where ingredient (iii) is present, and ingredient (iii) comprises water.

17. The composition of claim 16 , where the composition is an emulsion.

18. The composition according to claim 14 where the composition is a personal care composition adapted to provide a benefit to a portion of the body to which it is applied.