Photolabile latex for the release of perfumes

Patent metadata

Field	Value
Publication number	US-9315763-B2
Application number	US-201214349857-A
Country	US
Kind code	B2
Filing date	Sep 28, 2012
Priority date	Oct 6, 2011
Publication date	Apr 19, 2016
Grant date	Apr 19, 2016

Abstract

The present invention relates to the field of perfumery. More particularly, it concerns co-polymeric latex particles derived from 2-oxo-2-(3- or 4-vinylphenyl)acetates 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 latex in perfumery as well as the perfuming compositions or perfumed articles comprising the invention's latex.

First claim

What is claimed is:

1. A polymer microparticle capable of releasing in a controlled manner a perfuming aldehyde or ketone, said polymer microparticle comprising:
a) at least one repeating unit of formula

wherein A represents a benzene-1,4-diyl or a benzene-1,3-diyl moiety, and R is a group capable of releasing a C 6-20 perfuming aldehyde or perfuming ketone;

b) optionally at least one repeating cross-linking unit of formula

wherein all x are simultaneously either 0 or 1, y is 2, 3 or 4;
R 1 represents a C 2-12 hydrocarbon di-, tri- or tetra-radical depending upon the value of y, optionally comprising from 1 to 5 oxygen atoms; and
R 2 represents a hydrogen atom or a methyl group;
alternatively, the repeating cross-linking unit is of formula

c) optionally at least one repeating unit of the formulae

wherein L is an oxygen atom or a NH group, B represents a COOR 4 group, a C 6 H 5 , a C 6 H 4 COOR 4 , a OR 4 , a R 4 COO, a CON(R 4 ) 2 , a 2-oxopyrrolidin-1-yl group or a 2-oxoazepan-1-yl group, each R 3 is a hydrogen atom or a methyl group, and each R 4 represents a hydrogen atom, a C 1-4 alkyl group or a (C 2 H 4 O) q R 3 group, with q being an integer varying between 1 and 10.

2. A polymer microparticle according to claim 1 , wherein R is a group that is capable of releasing a C 6-15 perfuming aldehyde or ketone.

3. A polymer microparticle according to claim 1 , wherein R 1 represents a C 2-9 hydrocarbon di-, tri- or tetra-radical optionally comprising 1, 2, 3 or 4 oxygen atoms.

4. A polymer microparticle according to claim 1 , wherein R 2 represents a hydrogen atom and said R 3 represents a hydrogen atom.

5. A polymer microparticle according to claim 1 , wherein R 4 represents a hydrogen atom, or one of a methyl, ethyl, propyl, isopropyl or butyl group.

6. A polymer microparticle according to claim 1 , wherein x is 1.

7. A polymer microparticle according claim 1 , wherein B represents a COOH, a COOCH 3 , a C 6 H 5 , a C 6 H 4 COOH, a OH, a CH 3 COO, a CONH 2 , a 2-oxopyrrolidin-1-yl group or a 2-oxoazepan-1-yl group.

8. A polymer microparticle according to claim 1 , having an average size of the particle comprised in the range between 100 nm and 100 μm.

9. A polymer microparticle according to claim 1 , wherein one of the following units is present:
a repeating unit (I) obtained from the corresponding monomer (I′) that has a Hansen solubility parameter comprised between 15 and 25 (MPa) 0.5 ;
a repeating unit (II) or (III) obtained from the corresponding monomer (II′) or (III′) that has a Hansen solubility parameter comprised between 10 and 29 (MPa) 0.5 ; or
a repeating unit (IV-a), (IV-b) or (IV-c) obtained from the corresponding monomer (IV-a′), (IV-b′) or (IV-c′) that has a Hansen solubility parameter comprised between 15 and 29 (MPa) 0.5
wherein (I′), ( II′), (III′), (IV-a′), (IV-b′) and (IV-c′) have the following structures

wherein A and R have the meaning indicated in formula (I);

wherein x, y, R 1 and R 2 have the meaning indicated in formula (II);

wherein L, R 3 , R 4 and B have the meaning indicated in formulae (IV-a), (IV-b), (IV-c).

10. A perfuming composition comprising:
i) as perfuming ingredient, at least one polymer microparticle as defined in claim 1 ;
ii) at least one ingredient selected from the group consisting of a perfumery carrier and a perfumery base; and
iii) optionally at least one perfumery adjuvant.

11. A perfumed article comprising:
i) as perfuming ingredient, at least one polymer microparticle as defined in claim 1 ; and
ii) a consumer product base.

12. A perfumed article according to claim 11 , wherein the consumer product base is one of a solid or liquid detergent, a fabric softener, a perfume, a cologne, an after-shave lotion, a perfumed soap, a shower salt, a bath salt, a mousse, an oil, a gel, a hygiene product, a hair care product, a shampoo, a body-care product, a deodorant, an antiperspirant, an air freshener, a cosmetic preparation, a fabric refresher, an ironing water, a paper, a wipe or a bleach.

13. The polymer microparticle of claim 1 , wherein said perfuming aldehyde is 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-dimethyl-2,3-dihydro-1H-inden-5-yl)propanal, 3-(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-ethylphenyl)-2,2-dimethylpropanal, 3-(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-(4-hydroxy-4-methylpentyl)-3-cyclohexene-1-carbaldehyde, 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-methoxybenzaldehyde, 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-trimethyl-3-cyclohexene-1-carbaldehyde, 3,5,6-trimethyl

Assignees

• Firmenich & Cie

Inventors

• Herrmann Andreas
• Berthier Damien
• Paret Nicolas
• Therrien Myléne

Classifications

• C08F220/18

  with acrylic or methacrylic acids · CPC title

• Y10T428/2982

  Particulate matter [e.g., sphere, flake, etc.] · CPC title

• C11D3/505

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

• C08L31/02

  Homopolymers or copolymers of esters of monocarboxylic acids · CPC title

• A61K8/8152

  Homopolymers or copolymers of esters, e.g. (meth)acrylic acid esters; Compositions of derivatives of such polymers · CPC title