Targeted controlled delivery compositions activated by changes in pH or salt concentration

• US 7,053,034 B2
• Filed: 04/10/2002
• Issued: 05/30/2006
• Est. Priority Date: 04/10/2002
• Status: Active Grant

• Current Assignee: Salvona LLC
• Original Assignee: Salvona LLC
• Inventors: Shefer, Adi, Shefer, Shmuel David
• Primary Examiner(s): Douyon, Lorna M.
• Application Number:
  US10/119,567
• Publication Number:
  US 20030195133A1
• Time in Patent Office: 1,511 Days
• Field of Search: 510/441, 510/349, 510/101, 510/276, 510/515, 510/504, 510/513, 424/490, 424/491, 424/492, 424/493, 424/494, 424/496, 424/497, 424/498, 512/4
• US Class Current: 510/349
• CPC Class Codes: A61K 2800/413 Nanosized, i.e. having sizes below 100 nm
• CPC Class Codes: A61K 2800/56 Compounds, absorbed onto or entrapped into a solid carrier, e.g. encapsulated perfumes, inclusion compounds, sustained release forms
• CPC Class Codes: A61K 8/0287 the particulate containing a solid-in-solid dispersion
• CPC Class Codes: A61Q 13/00 Formulations or additives for perfume preparations essential oils or perfumes per se C11B9/00
• CPC Class Codes: B82Y 5/00 Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
• CPC Class Codes: C11D 17/0039 Coated compositions or coated components in the compositions, (micro)capsules
• CPC Class Codes: C11D 3/0047 pH regulated compositions
• CPC Class Codes: C11D 3/505 encapsulated or adsorbed on a carrier, e.g. zeolite or clay

Abstract

The present invention relates to a novel controlled release carrier system for pH or salt triggered release and targeted delivery of fragrances and other active ingredients onto fabric, hair, skin, and other biological surfaces and which provides prolonged release of fragrances and other active ingredients over an extended period of time, or yields a high impact fragrance “burst” upon treating the target surface with heat (blow drying the hair, ironing the fabric). The controlled delivery system of the present invention is substantially a free-flowing powder formed of solid hydrophobic nano-spheres comprising the fragrance and other active ingredients that are encapsulated in a pH or salt sensitive micro-spheres. Also described are processes for preparing such compositions and processes for using same. Furthermore, certain components of the aforementioned compositions in combination with one another are novel, and other components have novel uses in increasing fragrance substantivity, particularly in fabric, hair, and skin care preparations. The invention further pertains to consumer and diversified products comprising the controlled release system of the present invention.

Claims

1. A controlled release composition comprising:

a plurality of solid nano-spheres, each of said solid nano-spheres comprising an effective amount of a first active agent and a cationic surface active agent, said plurality of nano-spheres are formed of a hydrophobic material, said plurality of nano-spheres being encapsulated within a pH sensitive or salt sensitive micro-sphere, said pH sensitive or salt sensitive micro-sphere is formed of a pH sensitive or salt sensitive matrix material wherein each of said nano-spheres has an average size of about 0.05 to about 2 microns and said micro-sphere has a size of from about 2 microns to about 50 microns.

2. The composition of claim 1 wherein said hydrophobic material is selected from one or more of the group consisting of natural wax, synthetic wax, vegetable wax, natural wax and silicon copolymer, synthetic wax and silicon copolymer, fatty acid esters, fatty alcohols, solid hydrogenated plant oil, natural polymers and synthetic polymers.

3. The composition according to claim 1 wherein said pH sensitive micro-sphere degrades or dissolves when said pH sensitive micro-sphere contacts a solution having a pH in the range of about 3 to about 12.

4. The composition according to claim 1 wherein said pH sensitive micro-sphere degrades or dissolves when said pH sensitive micro-sphere contacts a solution having a pH in the range of about 7 to about 9.

5. The composition according to claim 1 wherein a first portion of said plurality of nano-spheres are adhered to a second portion of said plurality of nano-spheres with a pH sensitive or salt sensitive matrix material.

6. The composition according to claim 1 wherein said pH sensitive material is formed of a copolymer of acrylate, styrene and maleic acid copolymers, formalized gelatin, gluten, shellac, salol, keratin, keratin sandarac-tolu, ammoniated shellac, benzophenyl salicylate, cellulose acetate trimellitate, cellulose acetate blended with shellac, hydroxypropylmethyl cellulose acetate succinate, oxidized cellulose, polyacrylic acid derivatives, acrylic acid and acrylic ester copolymer, methacrylic acid and esters thereof vinyl acetate and crotonic acid copolymers.

7. The composition according to claim 1 wherein said pH sensitive material is formed of a copolymer having ionizable groups selected from the group consisting of polyphosphene, vinyl pyridine, vinyl aniline, polylysine, polyomithine, protein, and polymers with substituents containing amino moieties.

8. The composition according to claim 1 further comprising a moisture sensitive material mixed with said pH sensitive or salt sensitive material of said micro-sphere.

9. The composition according to claim 8 wherein said moisture sensitive material is selected from the group consisting of polyvinyl pyrrolidone, water soluble cellulose, polyvinyl alcohol, ethylene maleic anhydride copolymer, methyl vinyl ether maleic anhydride copolymer, polyethylene oxides, warer soluble polyamide, polyester, copolymers or homopolymers of acrylic acid, polyacrylic acid, polystyrene acrylic acid copolymer, starch derivatives, polysaccharide, hydrocolloid, natural gum, protein, and mixtures thereof.

10. The composition of claim 9 wherein said polyvinyl alcohol has a degree of hydrolysis from about 75% to about 99%.

11. The composition according to claim 1 wherein said cationic surface active agent is selected from the group consisting of cationic quatemary ammonium salts, acrylic quatemary ammonium salts having at least two C_8-30 alkyl chains;

diamido quatemary ammonium salts, biodegradable quatemary ammonium salts and tertiary fatty amines having at least one C₈ to C₃₀ alkyl chains.

12. The composition according to claim 1 wherein said cationic surface active agent is selected from the group consisting of ditallowdimethyl ammonium methylsulfate, di(hydrogenated tallow)dimethyl ammonium methylsulfate, distearyldimethyl ammonium methylsulfate, dicocodimethyl ammonium methylsulfate, ditallowdimethyl ammonium methylsulfate, di(hydrogenated tallow)dimethyl ammonium methylsulfate, distearyldimethyl ammonium methylsulfate, dicocodimethyl ammonium methylsulfate, methyl-bis(hydrogenated tallow amidoethyl)-2-hydroxyethyl ammonium methyl sulfate, methyl bis(tallowamidoethyl)-2-hydroxypropyl ammonium methylsulfate, N,N-di tallowoyl-oxy-ethyl)-N,N,-dimethyl ammonium methyl sulfate and N,N-di (tallowoyl-oxy-propyl)-N, N-dimethyl ammonium methyl sulfate and tallow-di-methylamine and cyclic amines, 1 -(hydrogenated tallow)amidoethyl-2-(hydrogenated tallow)imidazoline.

13. The composition according to claim 1 further comprising a cationic fabric conditioning agent selected from the group consisting of:

behenyltrimethylammonium chloride;

ditallowdimethylammonium methylsulfate;

ditallowdimethylammonium chloride;

methyl(1) stearylamidoethyl(2) stearylimidazolinium methosulfate;

methyl(1 )stearylamidoethyl(2)stearylimidazolinium chloride;

N,N-di(tallowyl-oxy-ethyl)-N,N-dimethyl ammonium chloride;

N,N-di(canolyl-oxy-ethyl)-N,N-dimethyl ammonium chloride;

N,N-di(tallowyl-oxy-ethyl)-N-methyl, N-(2-hydroxyethyl) ammonium chloride;

N,N-di(canolyl-oxy-ethyl)-N-methyl, N-(2-hydroxyethyl) ammonium chloride;

N,N-di(2-tallowyloxy-2-oxo-ethyl)-N,N-dimethyl ammonium chloride;

N,N-di(2-canolyloxy-2-oxo-ethyl)-N,N-dimethyl ammonium chloride;

N,N-di(2-tallowyloxyethylcarbonyloxyethyl)-N,N-dimethyl ammonium chloride;

N,N-di(2-canolyloxyethylcarbonyloxyethyl)-N,N-dimethyl ammonium chloride;

N-(2-tallowoyloxy-2-ethyl)-N-(2-tallowyloxy-2-oxo-ethyl)-N,N-dimethyl ammonium chloride;

N-(2-canolyloxy-2-ethyl)-N-(2-canolyloxy-2-oxo-ethyl)-N,N-dimethyl ammonium chloride;

N,N,N-tri (tallowyl-oxy-ethyl)-N-methyl ammonium chloride;

N,N,N-tricanolyl-oxy-ethyl)-N-methyl ammonium chloride;

N-(2-tallowyloxy-2-oxoethyl)-N-(tallowyl)-N,N-dimethyl ammonium chloride;

N-(2-canolyloxy-2-oxoethyl)-N-(canolyl)-N,N-dimethyl ammonium chloride;

1,2-ditallowyloxy-3 -N,N,N-trimethylammoniopropane chloride; and

1 ,2-dicanolyloxy-3 -N,N,N-trimethylammoniopropane chloride; and

mixtures of thereof.

14. The composition according to claim 1 wherein said first active agent is a fragrance.

15. The composition of claim 14 wherein said first active agent further comprises a conditioner selected from the group consisting of mineral oil, petrolatum, vegetable oils, soybean, maleated soybean oil, dimethicone, dimethicone copolyol, cationic monomers and polymers, guar hydroxypropyl trimonium chloride, distearyl dimethyl ammonium chloride and combinations thereof.

16. The composition of claim 1 wherein said first active agent is present in about 1% to about 80% by weight of said nano-spheres.

17. The composition of claim 1 wherein said pH sensitive matrix material is formed of a pH or salt sensitive material and polyvinyl alcohol in an amount of about 1% to about 50% by weight of the matrix material.

18. The composition of claim 1 wherein said pH sensitive matrix material is formed of a pH or salt sensitive material and about 1% to about 20% polyvinyl alcohol by weight of the matrix material and about 1% to about 20% polysaccharide by weight of the matrix.

19. The composition of claim 1 wherein said first active agent is released upon heat treatment of said nano-spheres.

20. The composition according to claim 1 wherein said composition comprises a free flowing powder.

21. A controlled release composition comprising:

a plurality of solid nano-spheres, each of said solid nano-spheres comprising an effective amount of a first active agent, and a cationic surface active agent said plurality of nano-spheres are formed of a hydrophobic material, said plurality of nano-spheres being encapsulated within a pH sensitive or salt sensitive micro-sphere, said pH sensitive or salt sensitive micro-sphere is formed of a pH sensitive or salt sensitive matrix material, and a second active agent encapsulated in said pH sensitive or salt sensitive matrix material wherein said pH sensitive or salt sensitive matrix material releases said second active agent upon contact with a solution having a predetermined pH in the range of about 3 to about 12 wherein each of said nano-spheres has an average size of about 0.05 to about 2 microns and said micro-sphere has a size of from about 2 microns to about 50 microns.

22. The composition according to claim 21 wherein said pH or salt sensitive material upon contact with said solution releases said second active agent to provide a burst and said first active agent is released continuously thereafter for an extended period of time.

23. The composition according to claim 22 wherein the extended period of time is in the range of a day to a period of a few weeks.

24. A controlled release composition comprising:

a plurality of solid nano-spheres, each of said solid nano-spheres comprising an effective amount of a first active agent, said plurality of nano-spheres are formed of a hydrophobic material, said plurality of nano-spheres being encapsulated within a pH sensitive or salt sensitive micro-sphere, said pH sensitive or salt sensitive micro-sphere is formed of a pH sensitive or salt sensitive matrix material, a cationic charge booster within said solid nano-sphere wherein each of said nano-spheres has an average size of about 0.05 to about 2 microns and said micro-sphere has a size of from about 2 microns to about 50 microns.

25. The system of claim 24 wherein said cationic charge booster is selected from the group consisting of a quatemary ammonium compound, polyvinyl amine, polyalkyleneimine, polyethyleneimine, and a poly-quatemary ammonium compound.

26. A fragrance carrier system comprising a composition comprising a plurality of solid nano-spheres including a fragrance and a cationic conditioning agent are formed of a hydrophobic material, said plurality of nano-spheres being encapsulated within a pH sensitive or salt sensitive micro-sphere, said pH sensitive or salt sensitive micro-sphere is formed of a pH sensitive or salt sensitive matrix material wherein each of said nano-spheres has an average size of about 0.05 to about 2 microns and said micro-sphere has a size of from about 2 microns to about 50 microns.

27. A fabric care product comprising the fragrance carrier system of claim 26.

28. The fabric care product of claim 27 wherein said product further comprises ironing aid, silicones, anti-shrinkage agent, anti-wrinkle agent, fabric crisping agent, spotting agent, germicide, fungicide, stabilizer, preservative, bactericide, flow agent, and mixtures thereof.

29. A method for forming a controlled release composition, said composition comprising:

a plurality of solid nano-spheres, each of said solid nano-spheres comprising an effective amount of a first active agent, comprising a fragrance said plurality of nano-spheres are formed of a hydrophobic material, said plurality of nano-spheres being encapsulated within a pH sensitive or salt sensitive micro-sphere, said pH sensitive or salt sensitive micro-sphere is formed of a pH sensitive or salt sensitive matrix material, a second active agent encapsulated in said pH sensitive or salt sensitive matrix material wherein said pH sensitive or salt sensitive matrix material releases said second active agent upon contact with a solution having a pH in the range of about 3 to about 12wherein said nano-spheres are formed of a hydrophobic material comprising the steps of;

heating said hydrophobic material to a temperature above the melting point to form a hot melt;

dissolving or dispersing said first active agent into the melt;

dissolving or dispersing said second active agent, and said pH or salt sensitive matrix material, in an aqueous phase and heating it to above the melting temperature of said hydrophobic material;

mixing the hot melt with said aqueous phase to form a dispersion;

high shear homogenization of the dispersion at a temperature above the melting temperature until a homogeneous fine dispersion is formed;

cooling the dispersion to ambient temperature to form an emulsified mixed suspension; and

spray drying the emulsified mixed suspension to form a dry powder composition.