FRAGRANT FORMULATIONS, METHODS OF MANUFACTURE THEREOF AND ARTICLES COMPRISING THE SAME

• US 20110274643A1
• Filed: 05/10/2011
• Published: 11/10/2011
• Est. Priority Date: 05/10/2010
• Status: Active Grant

• Current Assignee: GFBiochemicals Limited
• Original Assignee: Segetis Inc (GFBiochemicals Italy SpA)
• Inventors: Yontz, Dorie J.
• Granted Patent: US 9,301,910 B2
• Time in Patent Office: Days
• US Class Current: 424/76.1
• 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

Disclosed herein is a fragrant formulation comprising a fragrant composition, and an alkyl ketal ester. Disclosed herein too are methods for manufacturing the fragrant formulation.

Claims

1. A fragrant formulation comprising:

at least one fragrant composition, and

an alkyl ketal ester of formula (1)

2. The fragrant formulation of claim 1, wherein the fragrant composition is a flavorant.

3. The fragrant formulation of claim 1, wherein the fragrant composition is a perfume.

4. The fragrant formulation of claim 1, wherein the fragrant composition comprises a perfume and a flavorant.

5. The fragrant formulation of claim 1, wherein the alkyl ketal ester is selected from the group consisting of ethyl-LGK, ethyl-LPK, n-butyl-LGK, n-butyl-LPK or a combination comprising at least one of the foregoing alkyl ketal esters.

6. The fragrant 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.

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

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

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

10. The fragrant formulation of claim 1, further comprising water and a partially- or fully water-miscible alkyl ketal ester.

11. The fragrant formulation of claim 1, comprising an alcoholic phase or an alcohol-water mixture.

12. The fragrant 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 fragrant 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 fragrant formulation of claim 1, comprising from about 0.001 to about 40 percent by weight of the fragrant composition, based on the total weight of the formulation.

15. The fragrant formulation of claim 1, where the at least one fragrant composition is derived from berries, allspice, juniper, seeds, almond, anise, celery, cumin, nutmeg oil, bark, cassia, cinnamon, sassafras, wood, camphor, cedar, rosewood, sandalwood, agar wood, rhizome, galangal, ginger, leaves, basil, bay leaf, cinnamon, common sage, eucalyptus, lemon grass, melaleuca, oregano, patchouli, peppermint, pine, rosemary, spearmint, tea tree, thyme, wintergreen, resin, frankincense, myrrh, flowers, cannabis, chamomile, clary sage, clove, scented geranium, hops, hyssop, jasmine, lavender, manuka, marjoram, rose, rosemary, basil, lemon grass, ylang-ylang, peel, bergamot, grapefruit, lemon, lime, orange, tangerine, root, valerian, mango, or the like, or a combination comprising at least one of the foregoing.

16. The fragrant formulation of claim 1, where the at least one fragrant composition is derived from alcohols;

aldehydes;

esters;

ketones;

lactones;

thiols;

linear terpenes;

cyclic terpenes;

aromatic species;

amines, or a combination thereof.

17. The fragrant formulation of claim 16, where the alcohol is a furaneol, a 1-hexanol, a cis-3-hexen-1-ol, a menthol, or a combination comprising at least one of the foregoing alcohols;

where the aldehyde is an acetaldehyde, a hexanal, a cis-3-hexenal, a furfural or a combination comprising at least one of the foregoing aldehydes;

where the ester is a fructone, a hexyl acetate, an ethyl methylphenylglycidate, a methyl formate, a methyl acetate, a methyl butyrate, a methyl butanoate, an ethyl acetate, an ethyl butyrate, an ethyl butanoate, an isoamyl acetate, a pentyl butyrate, a pentyl butanoate, a pentyl pentanoate, or a combination comprising at least one of the foregoing esters;

where the ketone is a dihydrojasmone, an oct-1-en-3-one, a 2-acetyl-1-pyrroline, a 6-acetyl-2,3,4,5-tetrahydropyridine, or a combination comprising at least one of the foregoing ketones;

where the lactone is a γ

-decalactone, a γ

-nonalactone, a δ

-octalactone, or a combination comprising at least one of the foregoing lactones;

where the thiol is a ethanethiol, grapefruitmercaptan, a methanethiol, a 2-methyl-2-propanethiol or a combination comprising at least one of the foregoing lactones;

where the linear terpene is a myrcene, geraniol, nerol, citral, lemonal, geranial, neral, citronellal, citronellol, linalool, nerolidol, or a combination comprising at least one of the foregoing linear terpenes;

where the cyclic terpene is a limonene, camphor, terpincol, ionone, thujuon, or a combination comprising at least one of the foregoing cyclic terpenes;

where the aromatic species are benzaldehyde, eugenol, cinnamaldehyde, ethyl maltol, vanillin, anisole, anethole, estragole, thymol, or a combination comprising at least one of the foregoing aromatic species;

where the amines are thiethylamine, trimethylamine, cadaverine, pyridine, indole, skatole, or a combination comprising at least one of the foregoing amines.

18. The fragrant formulation of claim 1, where the at least one fragrant composition comprises geraniol, geranyl acetate, linalool, linalyl acetate, tetrahydrolinalool, citronellol, citronellyl acetate, dihydromyrcenol, dihydromyrcenyl acetate, tetrahydromyrcenol, terpineol, terpinyl acetate, nopol, nopyl acetate, 2-phenylethanol, 2-phenylethyl acetate, benzyl alcohol, benzyl acetate, benzyl salicylate, benzyl benzoate, styrallyl acetate, amyl salicylate, methyl salicylate, dimethylbenzyl carbinol, trichloromethylphenylcarbinyl acetate, p-tert.butyl-cyclohexyl acetate, isononyl acetate, vetiveryl acetate, vetiverol, alpha-n-amylcinammic aldehyde, alphah-hexylcinammic aldehyde, 2-methyl-3-(p-tert.butylphenyl)-propanol, 2-methyl-3-(p-isopropylphenyl)-prop anal, 3-(p-tert.butylphenyl)-propanal, tricyclodecenyl acetate, tricyclodecenyl propionate, 4-(4-hydroxy-4-methylpentyl)-3-cyclohexene carbaldehyde, 4-(4-methyl-3-pentenyl)-3-cyclohexene carbaldehyde, 4-acetoxy-3-pentyletetrahydropyran, methyl-dihydrojasmonate, 2-n-heptylcyclopentanone, 3-methyl-2-pentylcyclopentanone, n-decanal, 9-decenol-1, pehoxyethyl isobutyrate, phenylacetaldehyde dimethyl acetal, phenylacetaldehyde diethyl acetal, geranonitrile, citronellonitrile, cedryl acetate, 3-isocamphycyclohexanol, cedryl methyl ether, isolongifolanone, aubepine nitrile, aubepine, heliotropine, coumarin, eugenol, vanillin, diphenyl oxide, hydroxycitronellal, ionones, methylionones, isomethylioniones, irones, cis-3-hexenol and esters thereof, indane musk, tetralin musk, isochroman musk, macrocyclic ketones, macrolactone musk, ethylene brassylate, aromatic nitro-musk or combinations thereof.

19. The fragrant formulation of claim 1, further comprising a surfactant.

20. The fragrant formulation of claim 1, further comprising an antioxidant, an antiozonant, an antibacterial agent, a humectant, a colorant, a dye, a pigment, a food additive, a pheromone, a musk, a carbonate ion source, an alkalizing agent, a pH buffer, a conditioning agent, a chelant, an auxiliary agent, a solvent, a surfactant, a nonsurfactant suspending agent, an emulsifier, a skin conditioning agent, a hair conditioning agent, a hair fixative, a film-former, a skin protectant, a binder, a chelating agent, an antimicrobial agent, an antifungal agent, an antidandruff agent, an abrasive, an adhesive, an absorbent, a deodorant agent, a antiperspirant agent, an opacifying and pearlescing agent, a preservative, a propellant, a spreading aid, a sunscreen agent, a sunless skin tanning accelerator, an ultraviolet light absorber, a pH adjusting agent, a botanical, a hair colorant, an oxidizing agent, a reducing agent, a skin bleaching agent, a pigment, a physiologically active agent, an anti-inflammatory agent, a topical anesthetic, and fragrance solubilizer, a fragrance fixative a polymer, or a combination thereof.

21. The fragrant formulation of claim 1, which is in the form of a candle.

22. A method comprising:

blending a fragrant composition and an alkyl ketal ester of formula (I)

23. The method of claim 22, further comprising extracting the fragrant composition using the ketal adduct.

24. The method of claim 23, further comprising adding additional alkyl ketal ester to the fragrant formulation.

25. The method of claim 23, further comprising removing alkyl ketal ester from the fragrant formulation.

26. The method of claim 22, further comprising blending the fragrant composition with a compound, where the compound is an antioxidant, an antiozonant, an antibacterial agent, a humectant, a colorant, a dye, a pigment, a flavoring, a food additive, a pheromone, a musk, a carbonate ion source, an alkalizing agent, a pH buffer, a conditioning agent, a chelant, an auxiliary agent, a solvent, a surfactant, a nonsurfactant suspending agent, an emulsifier, a skin conditioning agent, a hair conditioning agent, a hair fixative, a film-former, a skin protectant, a binder, a chelating agent, an antimicrobial agent, an antifungal agent, an antidandruff agent, an abrasive, an adhesive, an absorbent, a dye, a deodorant agent, a antiperspirant agent, an opacifying and pearlescing agent, a preservative, a propellant, a spreading aid, a sunscreen agent, a sunless skin tanning accelerator, an ultraviolet light absorber, a pH adjusting agent, a botanical, a hair colorant, an oxidizing agent, a reducing agent, a skin bleaching agent, a pigment, a physiologically active agent, an anti-inflammatory agent, a topical anesthetic, a perfume and perfume solubilizer, a polymer, or a combination thereof. Plus what ever additions earlier in the claim set

27. An article comprising a fragrant composition and an alkyl ketal ester of formula (1):

28. The article of claim 27, which is selected from the group consisting of body lotions, shampoos, massage oils, perfume sticks and lanterns, air fresheners, candles, paints, varnishes, furniture care, insect repellents, in polymers, cleaners, detergents, cosmetics, toiletries, cosmeceuticals and beauty aids, and personal hygiene and cleansing products applied to the skin, hair, scalp, and nails of humans and animals.

29. The article of claim 27, which is in the form of a household care product.

30. The article of claim 27, which is in the form of a health care product.