Emulsions of fragrance releasing silicon compounds

• US 6,083,901 A
• Filed: 08/28/1998
• Issued: 07/04/2000
• Est. Priority Date: 08/28/1998
• Status: Expired due to Term

• Current Assignee: General Electric Company
• Original Assignee: General Electric Company
• Inventors: Liao, Wen P., Perry, Robert J.
• Primary Examiner(s): Brouillette, Gabrielle
• Assistant Examiner(s): Cole, Monique T.
• Application Number:
  US09/143,640
• Time in Patent Office: 676 Days
• Field of Search: 512/2, 512/4, 516/76, 516/104, 516/20
• US Class Current: 512/2
• CPC Class Codes: A61K 2800/57 Compounds covalently linked to a(n inert) carrier molecule, e.g. conjugates, pro-fragrances
• CPC Class Codes: A61K 8/585 Organosilicon compounds
• CPC Class Codes: A61K 8/891 saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
• CPC Class Codes: A61K 8/895 containing silicon bound to unsaturated aliphatic groups, e.g. vinyl dimethicone
• CPC Class Codes: A61Q 13/00 Formulations or additives for perfume preparations essential oils or perfumes per se C11B9/00

Abstract

Fragrance releasing silicon compounds either as siloxanes or silanes may be emulsified to form water-in-oil or oil-in-water emulsions. Further non-aqueous emulsions of two or more non-aqueous immiscible phases one of which contains a fragrance releasing silicon compound may be prepared by utilizing the emulsion stabilizing properties of a particulate elastomer dispersion in a volatile silicone compound.

Claims

1. A mixture comprising two immiscible liquid phases subject to the limitation that one of the two immiscible liquid phases comprises a fragrance releasing siloxane, wherein the fragrance releasing siloxane has the formula:

space="preserve" listing-type="equation">M.sub.f M.sub.g.sup.F D.sub.h D.sub.i.sup.F T.sub.j T.sub.k.sup.F Q.sub.l

where M has the formula R⁷ R⁸ R⁹ SiO_1/2 ;

M^F has the formula R⁷ R⁸ R^F SiO_1/2 ;

D has the formula R¹⁰ R¹¹ SiO_2/2 ;

D^F has the formula R¹⁰ R^F SiO_2/2 ;

T has the formula R¹² SiO_3/2 ;

T^F has the formula R^F SiO_3/2 ; and

Q has the formula SiO_4/2 where R⁷, R⁸, R⁹, R¹⁰, R¹¹ and R¹² are each independently selected for each M, M^F, D, D^F, T and T^F from the group of one to forty carbon atom monovalent alkyl or alkoxy radicals and one to forty carbon atom monovalent aryl or aryloxy radicals where the subscripts f or g are positive, and one or more of the subscripts h, i, j, k or l are positive, subject to the limitation that one of the subscripts g, i, or k is one or greater than one;

where R^F has the formula (R¹ O)_a (R² O)_b (R³ O)_c (R⁴)_d (R⁵)_e SiR^U with R^U a two to forty atom divalent hydrocarbon radical where R¹ O, R² O and R³ O are each independently fragrant alkoxide moieties, derived from the alcohols R¹ OH, R² OH and R³ OH wherein R¹ OH, R² OH and R³ OH are independently fragrant alcohols that are selected from the group consisting of 3-methyl-5-(2,2,3,-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol, 2-methylbutanol, 3-pentanol, n-pentanol, 2-pentanol, n-hexanol, 2-methylpentanol, 1-decanol, sandela, nonadyl, dimetol, thymol, 1-heptanol, menthol, eugenol, vanillan, o-vanillan, 4-(p-hydroxyphenyl)-2-butanone, syringealdehyde, prenol, cis-3-hexanol, trans-3-hexanol, cis-4-heptenol, trans-2-octenol, trans-2-cis-6-nonadienol, geraniol, nerol, citronellol, crotyl alcohol, oleyl alcohol, linalool, α

-terpineol, β

-phenethyl alcohol, cinnamic alcohol, benzyl alcohol, α

-methylbenzyl alcohol, nonyl alcohol, 1-octanol, 3-octanol, phenethyl salicylate, hydrocinnamyl alcohol, cis-6-nonen-1-ol, trans-2-nonen-1-ol, methyl salicylate, cis-3-octen-ol, anisyl alcohol, carvacrol, dihydrocarveol, benzyl salicylate, tetrahydrogeraniol, ethyl salicylate, ethyl vanillin, isoeugenol, isopulegol, lauryl alcohol, tetrahydrolinalool and 2-phenoxyethanol, with R⁴ and R⁵ selected from the group consisting of monovalent hydrocarbon radicals having from one to forty carbon atoms and monovalent alkoxy radicals having from one to forty carbon atoms, where the subscript a has a value ranging from 1 to 3 and the subscripts b, c, d, and e have values ranging from 0 to 2 subject to the limitation that a+b+c+d+e=3.

2. The mixture of claim 1 wherein said mixture comprises an emulsion.

3. The mixture of claim 2 wherein said emulsion is a microemulsion having an ASTM D871 haze below an upper limit of about 150.

4. The mixture of claim 2 further comprising a cross linked silicone gel having a Durometer hardness number, ASTM D-2240-91,of at least 5.

5. The mixture of claim 4 wherein the cross linked silicone gel having a Durometer hardness of at least 5 additionally possesses a particle size distribution characterized by three peaks or three local maxima in the particle size distribution:

1) a local maximum ranging from about 21 to about 26 microns,

     2) a local maximum ranging from about 33 to about 38 microns, and

     3) a local maximum ranging from about 50 to 60 microns.

6. The mixture of claim 5 wherein the emulsion comprises water.

7. The mixture of claim 5 wherein the emulsion is a non-aqueous emulsion.

8. cosmetic composition comprising the composition of claim 6.

9. A cosmetic composition comprising the composition of claim 7.

10. A mixture comprising two immiscible liquid phases wherein at least one of the two immiscible liquid phases comprises a fragrance releasing siloxane, wherein the fragrance releasing siloxane has the formula:

space="preserve" listing-type="equation">M.sub.f M.sub.g.sup.F D.sub.h D.sub.i.sup.F T.sub.j T.sub.k.sup.F Q.sub.l

where M has the formula R⁷ R⁸ R⁹ SiO_1/2 ;

M^F has the formula R⁷ R⁸ R^F SiO_1/2 ;

D has the formula R¹⁰ R¹¹ SiO_2/2 ;

D^F has the formula R¹⁰ R^F SiO_2/2 ;

T has the formula R¹² SiO_3/2 ;

T^F has the formula R^F SiO_3/2 ; and

Q has the formula SiO_4/2 where R⁷, R⁸, R⁹, R¹⁰, R¹¹ and R¹² are each independently selected for each M, M^F, D, D^F, T and T^F from the group of one to forty carbon atom monovalent alkyl or alkoxy radicals and one to forty carbon atom monovalent aryl or aryloxy radicals where the subscripts f or g are positive, and one or more of the subscripts h, i, j, k or I are positive, subject to the limitation that one of the subscripts g, i, or k is one or greater than one;

where R^F has the formula (R¹ O)_a (R² O)_b (R³ O)_c (R⁴)_d (R⁵)_e SiR^U with R^U a two to forty atom divalent hydrocarbon radical, where R¹, R² and R³ are derived from the group of fragrant esters, ketones, or aldehydes, each independently having the structure;

space="preserve" listing-type="equation">R.sup.7 --CH═

C(O--)--R.sup.8,

with R⁴ and R⁵ selected from the group consisting of monovalent hydrocarbon radical having from one to forty carbon atoms and monovalent alkoxy radicals having from one to forty carbon atoms, where the subscript a has a value ranging from 1 to 3 and the subscripts b, c, d, and e have values ranging from 0 to 2 subject to the limitation that a+b+c+d+e=3;

R⁷ is selected from the group consisting of hydrogen and monovalent hydrocarbon radicals having from one to one hundred carbon atoms and R⁸ is selected from the group consisting of hydrogen and monovalent hydrocarbon radicals having from one to one hundred carbon atoms where the subscript a has a value ranging from 1 to 3 and the subscripts b, c, d, and e have values ranging from 0 to 2 subject to the limitation that a+b+c+d+e=3.

11. The mixture of claim 10 wherein said mixture comprises an emulsion.

12. The mixture of claim 11 wherein said emulsion is a microemulsion having an ASTM D871 haze below an upper limit of about 150.

13. The mixture of claim 11 further comprising a cross linked silicone gel having a Durometer hardness number, ASTM D-2240-91,of at least 5.

14. The mixture of claim 13 wherein the cross linked silicone gel having a Durometer hardness of at least 5 additionally possesses a particle size distribution characterized by three peaks or three local maxima in the particle size distribution:

1) a local maximum ranging from about 21 to about 26 microns,

     2) a local maximum ranging from about 33 to about 38 microns, and

     3) a local maximum ranging from about 50 to 60 microns.

15. The mixture of claim 14 wherein the emulsion comprises water.

16. The mixture of claim 14 wherein the emulsion is a non-aqueous emulsion.

17. A cosmetic composition comprising the composition of claim 15.

18. A cosmetic composition comprising the composition of claim 16.