Emulsions containing saccharide siloxane copolymer emulsifiers and methods for their preparation and use

Patent metadata

Field	Value
Publication number	US-9492369-B2
Application number	US-201113817660-A
Country	US
Kind code	B2
Filing date	Aug 15, 2011
Priority date	Aug 23, 2010
Publication date	Nov 15, 2016
Grant date	Nov 15, 2016

Abstract

An emulsion contains a saccharide siloxane copolymer as an emulsifier. The emulsion is useful in formulating personal care products.

First claim

The invention claimed is:

1. A method of making a 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 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 acid anhydride functional group, or a lactone; each X is independently a divalent a carboxylic acid, phosphate, sulfate, sulfonate or quaternary ammonium radical, and
with the proviso that each R 3 and each R 4 may be the same or different;
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
iii) adding an oil, where step i) is performed by reacting ingredients comprising:
(A) an epoxy-functional polyorganosiloxane, and
(B) an n-alkyl glucamine.

2. The method of claim 1 , where ingredient (A) is

where
each R 12 is independently a monovalent hydrocarbon group;
each R 15 is independently an epoxy functional organic group;
each subscript x is independently 0 or 1;
subscript v has a value ranging from 0 to 10,000; and
subscript w has a value ranging from 0 to 10,000.

3. The method of claim 1 , where the n-alkyl glucamine is n-methyl glucamine.

4. The method of claim 1 , further comprising preparing the epoxy functional polyorganosiloxane by hydrosilylation of ingredients comprising an alkenyl functional epoxy containing compound and a polyorganohydrogensiloxane.

5. The method of claim 4 , where the alkenyl functional epoxy containing compound is allyl glycidyl ether, dodecyl glycidyl ether, tetradecyl glycidyl ether, or octadecylglycidyl ether.

6. The method of claim 1 , where the ingredients further comprise an alkene.

7. The method of claim 6 , where the alkene comprises undecene.

8. The method of claim 1 , 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.

9. The method of claim 8 , where the n-alkyl glucamine is n-methyl glucamine.

10. The method of claim 8 , where the alkenyl functional epoxy containing compound is allyl glycidyl ether, dodecyl glycidyl ether, tetradecyl glycidyl ether, or octadecylglycidyl ether.

11. The method of claim 1 , 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.

12. The method of claim 1 , where the solvent is an alcohol selected from methanol, ethanol, n-propanol, isopropanol, 2-propanol, isobutanol, n-butanol, and combinations thereof.

13. The method of claim 1 , where the oil is a silicone oil.

14. The method of claim 13 , where the oil is a polydialkylsiloxane.

15. The method of claim 1 , where the oil is an organic oil selected from a hydrocarbon oil, an ester, a vegetable oil, a mineral oil, or a fatty alcohol.

16. A method for preparing an emulsion comprising
I) adding an aqueous phase to the product prepared by the method of claim 1 , and
II) mixing.

17. The method of claim 16 , where the method further comprises step III) subjecting the emulsion to shear during and/or after step II).

18. The method of claim 16 , where step I) and step II) are performed incrementally by adding a portion of the aqueous phase, mixing, and thereafter repeating until all of the aqueous phase is added.

19. The method of claim 16 , where step I) and step II) are performed by adding the aqueous phase continuously over a period of time while mixing is performed.

20. The method of claim 16 , where the aqueous phase is present in an amount ranging from 20% to 95% by weight based on the weight of the emulsion.

21. An emulsion comprising:
A) an aqueous phase,
B) an oil phase having an oil, and
C) an emulsifier, where the emulsifier is a saccharide siloxane copolymer prepared by the method of claim 7 ,

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.

22. The emulsion of claim 21 , where the aqueous phase is discontinuous and the oil phase is continuous.

23. The emulsion of claim 21 where the oil phase comprises a silicone oil.

24. The emulsion of claim 23 , where the silicone oil is a polydialkylsiloxane.

25. The emulsion of claim 21 where the oil is an organic oil selected from a hydrocarbon oil, an ester, a vegetable oil, a mineral oil, or a fatty alcohol.

26. A composition comprising:
(A) the emulsion according to claim 21 , and
(B) an additional ingredient.

27. The composition of claim 26 , where ingredient (B) is selected from: additional silicones, aerosols, anti-oxidants, cleansing agents, colorants, additional conditioning agents, deposition agents, electrolytes, emollients and oils, exfoliating agents, foam boosters, fragrances, humectants, occlusive agents, pediculicides, pH control agents, pigments, preservatives, biocides, other solvents, stabilizers, sunscreening agents, suspending agents, tanning agents, other surfactants, thickeners, vitamins, botanicals, waxes, rheology-modifying agents, antiperspirants, anti-dandruff, anti-acne, anti-carie and wound healing-promotion agents, an additional oil, a hydrophilic medium, a filler, a fiber, a film forming polymer, an additional surfactant and/or emulsifier, a dyestuff, a structuring agent, an activ

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

• C08G77/42

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

• A61Q5/02

  Preparations for cleaning the hair · CPC title

• A61Q1/02

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

• A61Q15/00

  Anti-perspirants or body deodorants (deodorisation of air A61L9/00) · CPC title

• C08G77/388

  containing nitrogen · CPC title