PERSONAL CARE FORMULATIONS CONTAINING ALKYL KETAL ESTERS AND METHODS OF MANUFACTURE

• US 20150064124A1
• Filed: 11/07/2014
• Published: 03/05/2015
• Est. Priority Date: 05/10/2010
• Status: Active Grant

• Current Assignee: GFBiochemicals Limited
• Original Assignee: Segetis Inc (GFBiochemicals Italy SpA)
• Inventors: YONTZ, Dorie J., RIETH, Lee Richard, MORANTE, Nicholas, PALEFSKY, Irwin
• Granted Patent: US 9,549,886 B2
• Time in Patent Office: Days
• US Class Current: 424/59
• CPC Class Codes: A01N 25/00 Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application , e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
• CPC Class Codes: A61K 2800/49 Solubiliser, Solubilising system
• CPC Class Codes: A61K 47/22 Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones
• CPC Class Codes: A61K 8/25 Silicon; Compounds thereof
• CPC Class Codes: A61K 8/29 Titanium; Compounds thereof
• CPC Class Codes: A61K 8/31 Hydrocarbons
• CPC Class Codes: A61K 8/34 Alcohols
• CPC Class Codes: A61K 8/35 Ketones, e.g. benzophenone
• CPC Class Codes: A61K 8/368 with carboxyl groups directly bound to carbon atoms of aromatic rings
• CPC Class Codes: A61K 8/4953 containing pyrimidine ring derivatives, e.g. minoxidil
• CPC Class Codes: A61K 8/4973 with oxygen as the only hetero atom
• CPC Class Codes: A61K 8/498 having 6-membered rings or their condensed derivatives, e.g. coumarin
• CPC Class Codes: A61K 8/922 of vegetable origin
• CPC Class Codes: A61K 8/925 of animal origin
• CPC Class Codes: A61K 8/927 of insects, e.g. shellac
• CPC Class Codes: A61K 8/9789 Magnoliopsida [dicotyledons]
• CPC Class Codes: A61P 17/10 Anti-acne agents
• CPC Class Codes: A61P 31/00 Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
• CPC Class Codes: A61P 31/10 Antimycotics
• CPC Class Codes: A61Q 1/02 Preparations containing skin colorants, e.g. pigments preparations in powder form A61Q1/12
• CPC Class Codes: A61Q 1/04 : for lips
• CPC Class Codes: A61Q 1/06 : Lipsticks
• CPC Class Codes: A61Q 1/10 : for eyes, e.g. eyeliner, mascara
• CPC Class Codes: A61Q 1/12 : Face or body powders for grooming, adorning or absorbing
• CPC Class Codes: A61Q 15/00 : Anti-perspirants or body deodorants deodorisation of air A61L9/00
• CPC Class Codes: A61Q 17/04 : Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
• CPC Class Codes: A61Q 3/00 : Manicure or pedicure preparations
• CPC Class Codes: A61Q 5/10 : Preparations for permanently dyeing the hair
• CPC Class Codes: A61Q 9/04 : Depilatories
• CPC Class Codes: C08K 5/156 : having two oxygen atoms in the ring
• CPC Class Codes: C09D 7/45 : Anti-settling agents

Abstract

Personal care formulations containing alkyl ketal esters having the structure

wherein a is 0 or an integer of 1 to 12; b is 0 or 1; R² is a divalent C_1-8 group optionally substituted with up to 5 hydroxyl groups; and R¹ is C_1-6 alkyl.

Claims

1. A personal care formulation comprising an alkyl ketal ester, wherein the alkyl ketal ester is methyl-LPK, ethyl-LPK, n-butyl-LPK, ethyl-LEK, Me-AcAcGK, Et-AcAcGK, ethyl-LTMEK, ethyl-LTMPK, or a combination comprising at least one of the foregoing;

and

an active agent selected from organic anti-aging agents, organic anti-acne agents, organic skin whiteners, organic ultraviolet light absorbers, organic tanning agents, organic anti-alopecia agents, antifungal agents, anti-dandruff active agents, anti-perspirant active agents, antimicrobial agents, organic medicinals, depilatory compounds, hair dyes, organic insect repellants, and a combination thereof;

wherein methyl-LPK is of the formula;

2. The formulation of claim 1, wherein the active agent is lactic acid, 2-hydroxydecanoic acid, 2-hydroxyoctanoic acid and glycolic acid, beta-hydroxy acids such as beta-hydroxy salicylic acid, avobenzone, benzoate-4-methylbenzylidene, cinoxate, dioxybenzone, homosalate, menthyl anthranilate, mexoryl SX, drometrizole trisiloxane, octocrylene, octyl methoxycinnamate, ethylhexyl salicylate, oxybenzone, padimate O,p-aminobenzoic acid (PABA), phenylbenzimidazole sulfonic acid, sulisobenzone, titanium trolamine salicylate, salicylic acid, a retinoic acid, benzoyl peroxide, hydroquinone, arbutun, a plant extract containing arbuten, kojic acid, azelaic acid, glycyrrhetic acid, levulinic acid, 2-cyano-3,3-diphenylacrylic acid, sodium benzotriazolyl butylphenol sulfonate, ethyl-2-cyan-3,3-diphenylacrylate, 2-t-butyl-6-(5-chloro-2H-benzotriazol-2-yl)-p-cresol, 2-(2-H-benzotriazol-2-yl)-4-methylphenol, benzophenone-12, bornelone, 2-benzotriazolyl-4-tert-octylphenol, dihydroxyacetone, erythrulose, dihydroxyacetone-ortho-ethyl acetate, canthaxanthin, afamelanotide, minoxidil, finasteride, dutasteride, ketoconazole, zinc pyrithione, selenium sulfide, clotrimazole, tea tree oil, piroctone olamine, an amphetamine, an antihistamine, methylphenidate, oxymetazoline, tetrahydrolzoline hydrochloride, psilocybin calcium, thioglycolate, sodium thioglycolate, thioglycolic acid, ammonium thioglycolate, butyl thioglycolate, ethanolamine thioglycolate, glyceryl thioglycolate, isooctyl thioglycolate, isopropyl thioglycolate, magnesium thioglycolate, methyl thioglycolate, potassium thioglycolate, aluminum zirconium tetrachlorohydrex gly, aluminum chlorohydrate, aluminum chloride, resorcinol, 1-napthol, p-aminophenol, p-phenylenediamine, salts of p-phenylenediamine, 4-amino-2-hydroxytoluene, phenoxyethanol, N,N-diethyl-m-toluamide, p-menthane-3,8-diol, nepetalactone, citronella oil, permethrin, neem oil, bog myrtle extract, or a combination comprising at least one of the foregoing active agents.

3. The formulation of claim 1, comprising from 0.001 to 40% by weight of the active agent, based on the total weight of the personal care formulation.

4. The formulation of claim 2, comprising from 0.001 to 30% by weight of the active agent and from 2 to 60% by weight of water, each based on the total weight of the personal care formulation.

5. The formulation of claim 1, further comprising at least one of

(a) a paraffinic, naphthenic, or aromatic mineral oil,

(b) a nonionic organic compound having

a melting temperature of less than 45°

C.,

a molecular weight of at least 190 Daltons,

an amido or ester group, and

an alkyl chain containing at least 8 carbon atoms, and

a solubility in water of no greater than 1 part in 99 parts of water;

(c) a nonionic organosilicone compound having

a melting temperature of less than 45°

C., and

a solubility in water of no greater than 1 part in 99 parts of water;

(d) a long chain alcohol; and

(e) a wax.

6. The formulation of claim 1, comprising at least one fully water miscible alkyl ketal ester.

7. The formulation of claim 1, comprising at least one partially water-miscible alkyl ketal ester.

8. The formulation of claim 1, comprising at least one sparingly water-miscible alkyl ketal ester.

9. The formulation of claim 1, comprising water and a partially- or fully water-miscible alkyl ketal ester which together form a cosolvent mixture into which at least one active is dissolved.

10. The formulation of claim 1, comprising an alcoholic phase or an alcohol-water phase, and an alkyl ketal ester that is miscible in the alcohol to the extent of at least 10 parts of the alkyl ketal ester in 90 parts by weight of the alcohol, wherein the alkyl ketal ester and at least one active agent is at least partially dissolved into the alcoholic phase or alcohol-water phase.

11. The formulation of claim 9, wherein the alcohol is ethanol, isopropanol, 1,2-propylene glycol, or 1,3-propane diol.

12. The formulation of claim 1, in the form of an emulsion comprising an aqueous phase and an oil phase, wherein the aqueous phase comprises the alkyl ketal ester, and the alkyl ketal ester is partially or fully water-miscible.

13. The formulation of claim 1, in the form of an emulsion comprising an aqueous phase and an oil phase, wherein the oil phase comprises the alkyl ketal ester.

14. The formulation of claim 1, wherein the alkyl ketal ester is ethyl-LPK, n-butyl-LPK or a combination comprising at least one of the foregoing alkyl ketal esters.

15. The formulation of claim 1, further comprising at least one fragrance.

16. The formulation of claim 1, further comprising at least one surfactant.

17. The formulation of claim 1, further comprising nitrocellulose, modified corn starch, acrylates/octylacrylamide copolymer, polyurethane-14 and AMP-acrylates copolymer, hydrolyzed wheat protein, polyvinylpyridine, hydrolyzed wheat protein/PVP crosspolymer, vinyl acetate/crotonates/vinyl neodecanoate copolymers, potassium butyl ester of PVM/MA copolymer, polyurethane-14 and AMP-acrylates copolymer, isobutylene/ethyl maleimide/hydroxylethylmaleimide copolymer, polyvinylpyrrolidine/vinyl acetate polymers, acrylates/hydroxyesters acrylates copolymer, polyurethanes, polyvinyl methyl ester/maleate, octylacrylamide/acrylates/butylaminoethyl methacrylate copolymer, or a combination comprising at least one of the foregoing polymers.

18. A waxy personal care formulation comprising

a wax,

an emollient, and

an alkyl ketal ester, wherein the alkyl ketal ester is methyl-LPK, ethyl-LPK, n-butyl-LPK, ethyl-LEK, Me-AcAcGK, Et-AcAcGK, ethyl-LTMEK, ethyl-LTMPK, or a combination comprising at least one of the foregoing;

wherein methyl-LPK is of the formula;

19. The formulation of claim 18, further comprising from 0.5 to 10% by weight of a polar compound, based on the total weight of the formulation.

20. The formulation of claim 19, wherein the polar compound is water.

21. The formulation of claim 18, wherein the alkyl ketal ester is ethyl-LPK, n-butyl-LPK or a combination comprising at least one of the foregoing alkyl ketal esters.

22. A personal care formulation in the form of an emulsion, comprising

i) a continuous phase and a disperse phase wherein the continuous phase or the disperse phase is an aqueous phase and the other is an oil phase;

or at least two co-continuous phases wherein at least one of the co-continuous phases is an aqueous phase and at least one of the co-continuous phases is an oil phase; and

wherein any of the foregoing oil phases comprises at least one of

(a) a paraffinic, naphthenic, or aromatic mineral oil,

(b) a nonionic organic compound having

a melting temperature of less than 45°

C.,

a molecular weight of at least 190 Daltons,

an amido or ester group, and

an alkyl chain containing at least 8 carbon atoms, and

a solubility in water of no greater than 1 part in 99 parts of water,

(c) a nonionic organosilicone compound having

a melting temperature of less than 45°

C., and

a solubility in water of no greater than 1 part in 99 parts of water,

(d) a long chain alcohol, and

(e) a wax; and

ii) an alkyl ketal ester, wherein the alkyl ketal ester is methyl-LPK, ethyl-LPK, n-butyl-LPK, ethyl-LEK, Me-AcAcGK, Et-AcAcGK, ethyl-LTMEK, ethyl-LTMPK, or a combination comprising at least one of the foregoing;

wherein methyl-LPK is of the formula;

23. The formulation of claim 22, wherein the alkyl ketal ester is a partially or fully water-miscible alkyl ester located at least partially in the aqueous phase.

24. The formulation of claim 22, wherein the alkyl ketal ester is ethyl-LPK, n-butyl-LPK, or a combination comprising at least one of the foregoing.

25. The formulation of claim 24, wherein the alkyl ketal ester is at least partially located in the oil phase.

26. A personal care formulation comprising

an alkyl ketal ester, wherein the alkyl ketal ester is methyl-LPK, ethyl-LPK, n-butyl-LPK, ethyl-LEK, Me-AcAcGK, Et-AcAcGK, ethyl-LTMEK, ethyl-LTMPK, or a combination comprising at least one of the foregoing;

and

an additional cosmetically acceptable ingredient;

wherein methyl-LPK is of the formula;

27. The formulation of claim 26, in the form of a solution, dispersion, emulsion, gel, ointment, or solid.

28. The formulation of claim 26, comprising an aqueous phase, an alcohol phase, or an alcohol/water phase in which at least a portion of the alkyl ketal ester is dissolved.

29. The formulation of claim 26 which is an emulsion that contains at least one aqueous phase and at least one oil phase, and the alkyl ketal ester is in the aqueous phase, the oil phase, both the aqueous and oil phases, or at the interface between the aqueous and oil phases.

30. The formulation of claim 26, which is a solution that contains water and an alkyl ketal ester dissolved in the water, and wherein at least one of said cosmetically acceptable ingredients is immiscible in water but is dissolved in the water/alkyl ketal ester mixture.

31. The formulation of claim 26, wherein the alkyl ketal ester is selected from ethyl-LPK, n-butyl-LPK, and combinations thereof.