Microcapsules and uses thereof

Patent metadata

Field	Value
Publication number	US-9334464-B2
Application number	US-201214361389-A
Country	US
Kind code	B2
Filing date	Nov 26, 2012
Priority date	Nov 29, 2011
Publication date	May 10, 2016
Grant date	May 10, 2016

Abstract

The present invention relates to core-shell microcapsules comprising photolabile 2-oxoacetate pro-fragrance molecules capable of liberating an active molecule such as, for example, an aldehyde or ketone upon exposure to light. The present invention concerns also the use of said microcapsules in perfumery as well as the perfuming compositions or perfumed articles comprising the invention's microcapsules to provide a prolonged release of fragrant aldehydes and/or ketones.

First claim

What is claimed is:

1. A core-shell microcapsule comprising:
a) a core of an oily phase containing at least one photolabile pro-fragrance ingredient which is a 2-oxoacetate derivative of formula

wherein,
R 1 represents a linear, branched or cyclic, saturated or unsaturated C 1 -C 16 hydrocarbon group, optionally substituted with one or two methoxy groups, and R 2 is a CH(R′)(R″) group derived from the corresponding C 6-20 perfuming aldehyde of formula (R″)CHO or C 6-20 perfuming ketone of formula (R′)(R″)C═O; and

b) a shell surrounding said core and formed by interfacial polymerisation or by a polymerisation induced phase separation process;
wherein the photolabile pro-fragrance ingredient releases a fragrant aldehyde or ketone when exposed to light by transforming the OR 2 moiety into a perfuming aldehyde (R″)CHO or ketone (R′)(R″)C═O, with simultaneous formation of a R 1 COOH or R 1 CHO residue.

2. A microcapsule according to claim 1 , comprising at least one pro-fragrance ingredient of formula (I) wherein R 1 represents a linear, branched or cyclic C 1 -C 10 hydrocarbon group.

3. A microcapsule according to claim 1 , comprising at least one pro-fragrance ingredient of formula (I) wherein R 1 represents a methyl, ethyl, tert-butyl, isopropyl, cyclopentyl or cyclohexyl group or a phenyl group optionally substituted with one or two methoxy groups.

4. A microcapsule according to claim 1 , comprising at least one pro-fragrance ingredient of formula (I) wherein R 2 is derived from an aldehyde selected from the group consisting of benzaldehyde, 1,3-benzodioxol-5-carboxaldehyde, 3-(1,3-benzodioxol-5-yl)-2-methylpropanal, 3-(4-tert-butyl-1-cyclohexen-1-yl)propanal, 2,4-decadienal, 2-decenal, 4-decenal, 8-decenal, 9-decenal, 3-(6,6-dimethyl-bicyclo[3.1.1]hept-2-en-2-yl)propanal, 2,4-dimethyl-3-cyclohexene-1-carbaldehyde, 3,5-dimethyl-3-cyclohexene-1-carbaldehyde, 1-(3,3-dimethyl-1-cyclohexyl)-1-ethanone, 5,9-dimethyl-4,8-decadienal, 3-(3,3- and 1,1-dimethyl-2,3-dihydro-1H-inden-5-yl)propanal, 2,6-dimethyl-5-heptenal, 3,7-dimethyl-2,6-octadienal, 3,7-dimethyloctanal, 3,7-dimethyl-6-octenal, (3,7-dimethyl-6-octenyl)acetaldehyde, 3-dodecenal, 4-dodecenal, 3-ethoxy-4-hydroxybenzaldehyde, 4-ethyl benzaldehyde, 3-(2 and 4-ethylphenyl)-2,2-dimethylpropanal, 2-furancarbaldehyde, 2,4-heptadienal, 3,5,5,6,7,8,8-heptamethyl-5,6,7,8-tetrahydronaphthalene-2-carbaldehyde, 4-heptenal, 2-hexenal, 3-hexenal, 2-hexyl-3-phenyl-2-propenal, 2-hydroxybenzaldehyde, 7-hydroxy-3,7-dimethyloctanal, 4-hydroxy-3-methoxybenzaldehyde, 4- and 3-(4-hydroxy-4-methylpentyl)-3-cyclohexene-1-carbaldehyde, 4-isopropylbenzaldehyde, 8-isopropyl-6-methyl-bicyclo[2.2.2]oct-5-ene-2-carbaldehyde, 3-(4-isopropylphenyl)-2-methylpropanal, 2-(4-isopropylphenyl)propanal, 2- and 4-methoxybenzaldehyde, 6-methoxy-2,6-dimethylheptanal, 3-(2-methoxyphenyl)acrylaldehyde, 8(9)-methoxy-tricyclo[5.2.1,0.(2,6)]decane-3(4)-carbaldehyde, 4-methylbenzaldehyde, 3-(4-methylcyclohex-3-en-1-yl)butanal, 2-(4-methylenecyclohexyl)propanal, 1-methyl-4-(4-methyl-3-pentenyl)-3-cyclohexen-1-carbaldehyde, 3-(4-methyl-3-pentenyl)-3-cyclohexene-1-carbaldehyde, 4-(4-methyl-3-pentenyl)-3-cyclohexene-1-carbaldehyde, (4-methylphenoxy)acetaldehyde, (4-methylphenyl)acetaldehyde, 3-methyl-5-phenylpentanal, 2-(1-methylpropyl)-1-cyclohexanone, 2-methyl-4-(2′,2′,3′-trimethyl-3′-cyclopentenyl)-4-pentenal, 2,4-nonadienal, 2,6-nonadienal, 2-nonenal, 3-nonenal, 6-nonenal, 8-nonenal, 2-octenal, 2-pentyl-3-phenyl-2-propenal, phenoxyacetaldehyde, 2-phenylacetaldehyde, 3-phenylbutanal, 3-phenylpropanal, 2-phenylpropanal, 3-phenyl-2-propenal, 4-(prop-1-en-2-yl)cyclohex-1-enecarbaldehyde, 3-(4-tert-butylphenyl)-2-methylpropanal, 3-(4-tert-butylphenyl)propanal, tricyclo[5.2.1,0(2,6)]decane-4-carbaldehyde, exo-tricyclo[5.2.1,0(2,6)]decane-8exo-carbaldehyde, 2,6,6-trimethyl-bicyclo[3.1.1]heptane-3-carbaldehyde, 2,4,6- and 3,5,6-trimethyl-3-cyclohexene-1-carbaldehyde, 2,2,3-trimethyl-3-cyclopentene-1-acetaldehyde, 2,6,10-trimethyl-2,6,9,11-dodecatetraenal, 2,5,6-trimethyl-4-heptenal, 3,5,5-trimethylhexanal, 2,6,10-trimethyl-9-undecenal, 2-undecenal, 10-undecenal or 9-undecenal and their mixtures, an aldehyde of formula (R″)CHO wherein R″ is a linear or α-branched alkyl group of C 6 to C 15 , and their mixtures.

5. A microcapsule according to claim 1 , comprising at least one pro-fragrance ingredient of formula (I) wherein R 2 is derived from a ketone selected from the group consisting of a damascenone, a damascene, a ionone or methyl ionone, irone, macrocyclic ketone such as, for example, cyclopentadecanone or 3-methyl-4-cyclopentadecen-1-one and 3-methyl-5-cyclopentadecen-1-one or 3-methyl-1-cyclopentadecanone, 1-(2-aminophenyl)-1-ethanone, 1-(3,3-dimethyl-1-cyclohexen-1-yl)-4-penten-1-one, 1-(5,5-dimethyl-1-cyclohexen-1-yl)-4-penten-1-one, 1-(3,3-dimethyl-1-cyclohexyl)-1-ethanone, 2,5-dimethyl-2-octene-6-one, 4,7-dimethyl-6-octene-3-one, (3,7-dimethyl-6-octenyloxy)acetaldehyde, 1-(2,4-dimethylphenyl)-1-ethanone, 4-(1,1-dimethylpropyl)-1-cyclohexanone, 2,4-di-tert-butyl-1-cyclohexanone, ethyl 4-oxopentanoate, 1-(4-ethylphenyl)-1-ethanone, 1-(3,5,5,6,8,8-hexamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)ethanone, 2-hexyl-1-cyclopentanone, 2-hydroxy-3-methyl-2-cyclopenten-1-one, 4-(4-hydroxy-1-phenyl)-2-butanone, 1-(2- and 4-hydroxyphenyl)-1-ethanone, 2-isopropyl-5-methylcyclohexanone, 4-isopropyl-2-cyclohexen-1-one, 1-(5-isopropyl-2-methylcyclohex-1- or 2-en-1-yl)propanone, 1-(4-isopropyl-1-phenyl)-1-ethanone, 2-(2-mercaptopropan-2-yl)-5-methylcyclohexanone, 1-(4-methoxyphenyl)-1-ethanone, 7-methyl-2H,4H-1,5-benzodioxepin-3-one, 5-methyl-3-heptanone, 6-methyl-5-hepten-2-one, methyl 3-oxo-2-pentyl-1-cyclopentaneacetate, 1-(4-methylphenyl)-1-ethanone, 5-methyl-2-(propan-2-ylidene)cyclohexanone, 5-methyl-2-(prop-1-en-2-yl)cyclohexanone, 2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enone, 5-methyl-exo-tricyclo[6.2.1,0(2,7)]undecan-4-one, 3-methyl-4-(1,2,2-trimethylpropyl)-4-penten-2-one, 2-naphthalenyl-1-ethanone, 1-(octahydro-2,3,8,8-tetramethyl-2-naphthalenyl)-1-ethanone, 3,4,5,6,6-pentamethyl-3-hepten-2-one, 2-pentyl-1-cyclopentanone, 4-phenyl-2-butanone, 1-phenyl-1-ethanone, 2- and 4-tert-butyl-1-cyclohexanone, 1-(4-tert-butylphenyl)-1-ethanone), 3,5,6,6-tetramethyl-4-methyleneheptan-2-one, 2,4,4,7-tetramethyl-6-octen-3-one, 1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-one, 2,6,6-trimethyl-1-cycloheptanone, 2,6,6-trimethyl-2-cyclohexene-1,4-dione, 4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-2-butanone, 1-(2,4,4-trimethyl-2-cyclohexen-1-yl)-2-buten-1-one, 1-(3,5,6-trimethyl-3-cyclohexen-1-yl)-1-ethanone, 2,2,5-trimethyl-5-pentyl-1-cyclopentanone or a C 6-15 ketone of formula (R′)(R″)C=o wherein R′ and R″ are linear alkyl groups, and their mixtures.

6. A microcapsule according to claim 1 , comprising at least one pro-fragrance ingredient of formula (I) selected from the group consisting of 3-(4-tert-butyl-1-cyclohexen-1-yl)propyl 2-oxo-2-phenylacetate, 3-(4-tert-butylphenyl)-2-methylpropyl 2-cyclohexyl-2-oxoacetate, 3-(4-(tert-butyl)phenyl)-2-methylpropyl 2-oxo-2-phenylacetate, decyl 2-cyclohexyl-2-oxoacetate, decyl 2-oxo-2-phenylacetate, (2,4-dimethyl-3-cyclohexen-1-yl)methyl 2-cyclohexyl-2-oxoacetate, (2,4-dimethyl-3-cyclohexen-1-yl)methyl 2-oxo-2-phenylacetate, 1-(3,3- and 5,5-dimethyl-1-cyclohexen-1-yl)-4-pentenyl 2-oxo2-phenylacetate, 3-(3,3- and 1,1-dimethyl-2,3-dihydro-1H-inden-5-yl)propyl 2-oxo-2-phenylacetate, 2,6-dimethyl-5-heptenyl 2-oxo-2-phenylacetate, 3,7-dimethyl-2,6-octadienyl 2-cyclohexyl-2-oxoacetate, 3,7-dimethyl-2,6-octadienyl 2-(4-methylcyclohexyl)-2-oxoacetate, 3,7-dimethyl-2,6-octadienyl 3-methyl-2-oxopentanoate, 3,7-dimethyl-2,6-octadienyl 2-oxo-2-phenylacetate, 3

Assignees

• Firmenich & Cie

Inventors

• Berthier Damien
• Herrmann Andreas
• Paret Nicolas
• Ouali Lahoussine

Classifications

• B01J13/06 Primary

  by phase separation · CPC title

• C11B9/0019 Primary

  carbocylic acids; Salts or esters thereof · CPC title

• C11D3/505

  encapsulated or adsorbed on a carrier, e.g. zeolite or clay · CPC title

• B01J13/16

  Interfacial polymerisation · CPC title