Microcapsules containing a gas-generating photolabile ketoacid or ketoester and uses thereof

Patent metadata

Field	Value
Publication number	US-9738859-B2
Application number	US-201414893518-A
Country	US
Kind code	B2
Filing date	May 20, 2014
Priority date	May 22, 2013
Publication date	Aug 22, 2017
Grant date	Aug 22, 2017

Abstract

The present invention relates to water-dispersable microcapsules comprising an oil phase, e.g. a perfume, containing a photolabile α-ketoacid or α-ketoester capable of generating a gas upon exposure to light. The gas is able to cause an extension or the breaking of the microcapsule allowing the release of the oil phase and thus increasing the long-lastingness of the odor perception. 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 molecules.

First claim

What is claimed is:

1. A non-diffusive microcapsule comprising;
A. a core comprising:
an oil phase;
at least one photolabile α-ketoacid or α-ketoester capable of generating, upon exposure to light a gas of CO or CO 2 and being of formula

wherein R 1 represents:
i) a C 1-16 hydrocarbon group optionally comprising one to four oxygen, sulphur or nitrogen atoms, provided that no heteroatom is directly connected to the CO group; or
ii) a group of formula R 1′ (CO—COOR 2 ) n wherein R 2 has the same meaning as below and R 1′ is a C 2-10 hydrocarbon group, optionally comprising one or two oxygen or nitrogen atoms, provided that no heteroatom is directly connected to the CO group, wherein R 1′ is linked to the keto functional group of the α-ketoacid or α-ketoester and wherein n is an integer comprised between 1 and 4;

and wherein R 2 represents either a hydrogen atom or an alkaline metal ion, or a primary or secondary group which is:
a) a C 1-4 hydrocarbon group optionally comprising one or two oxygen or nitrogen atoms; or
b) a C 5-22 hydrocarbon group optionally comprising one to ten oxygen atoms or one to two nitrogen atoms; provided that said C 5-22 hydrocarbon group is such as that the corresponding aldehyde or ketone of the O—R 2 moiety is an odorless compound; or
c) a group of formula R 2′ (OOC—CO—R 1 ), wherein R 1 has the same meaning as above and R 2′ is a C 2-12 hydrocarbon group optionally comprising one to six oxygen atoms and wherein R 2′ is linked to the ester functional group of the α-ketoester, and wherein n is an integer comprised between 1 and 4;
provided that at least one of R 1 or R 2 is a group as defined in i) or a) or b) respectively; and
optionally comprising at least one photo-catalyst; and

B. a shell surrounding said core formed by interfacial polymerization or by a phase separation process induced by polymerization or by coacervation;
wherein the amount of gas generated upon exposure to light is sufficient to expand and break the shell to release the oil from the capsule.

2. A microcapsule according to claim 1 , characterized in that it comprises, based on the total microcapsule weight, from about 20% to about 96% of oil phase.

3. A microcapsule according to claim 1 , characterized in that R 1 represents:
i) a C 1-10 hydrocarbon group optionally comprising one or two oxygen, sulphur or nitrogen atoms, provided that no heteroatom is directly connected to the CO group; or
ii) a group of formula R 1′ (CO—COOR 2 ) n wherein R 2 has the meaning set in claim 1 ; R 1′ is a C 2-6 hydrocarbon group and n is equal to 1 or 2.

4. A microcapsule according to claim 1 , characterized in that R 2 represents a hydrogen atom or a primary or secondary group which is:
a) a C 2-4 hydrocarbon group optionally comprising one or two oxygen or nitrogen atoms; or
b) a C 5-16 hydrocarbon group optionally comprising one to seven oxygen atoms or one or two nitrogen atoms; provided that said C 5-16 hydrocarbon group is such as that the corresponding aldehyde or ketone of the O—R 2 moiety is an odorless compound; or
c) a group of formula R 2′ (OOC—CO—R 1 ) n wherein R 1 has the meaning set in claim 1 and R 2′ is a C 2-6 hydrocarbon group optionally comprising one or two oxygen atoms and n is equal to 1 or 2.

5. A microcapsule according to claim 1 , characterized in that said α-ketoacid or α-ketoester generates a gas upon exposure to light at a wavelength comprised between 450 and 320 nm.

6. A microcapsule according to claim 1 , characterized in that it comprises, based on the total microcapsule weight, from 10% to 50% of photolabile α-ketoacid or α-ketoester.

7. A microcapsule according to claim 1 , characterized in that the shell surrounding said core is an aminoplast, polyamide, polyester, polyurea or polyurethane resin or a mixture thereof.

8. A microcapsule according to claim 1 , characterized in that said shell has a thickness varying between 20 and 500 nm.

9. A microcapsule according to claim 1 , characterized in that the oil phase comprises a perfuming oil.

10. A perfuming consumer product comprising:
i) as perfuming ingredient, at least one microcapsule as defined in claim 9 ; and
ii) as an option a free perfume oil.

11. A perfuming consumer product according to claim 10 , characterized in that the consumer product is a perfume, a fabric care product, a body-care product, an air care product or a home care product.

12. A perfuming consumer product according to claim 10 , characterized in that the consumer product is a fine perfume, a cologne, an after-shave lotion, a liquid or solid detergent, a fabric softener, a fabric refresher, an ironing water, a paper, a bleach, a shampoo, a coloring preparation, a hair spray, a vanishing cream, a deodorant or antiperspirant, a perfumed soap, shower or bath mousse, oil or gel, a hygiene product, an air freshener, a “ready to use” powdered air freshener, a wipe, a dish detergent or hard-surface detergent.

13. A method to release a perfume from a microcapsule as defined in claim 9 , characterized in that said microcapsule is exposed to conditions allowing the degradation of the photolabile α-ketoacid or α-ketoester of formula (I) with concomitant formation of a gas at a rate above 8.0×10 −5 s −1 in order to break the shell to release the oil from the capsule.

14. A method to release a perfume from a microcapsule as defined in claim 9 , characterized in that said microcapsule is exposed to conditions allowing the degradation of the photolabile α-ketoacid or α-ketoester of formula (I) with concomitant formation of a gas at a rate above 1.0×10 −4 s −1 in order to break the shell to release the oil from the capsule.

15. A non-diffusive microcapsule comprising:
A. a core comprising:
an oil phase;
at least one photolabile α-ketoacid or α-ketoester capable of generating, upon exposure to light a gas of CO or CO 2 and being of formula

wherein R 1 represents:
i) a C 1-16 hydrocarbon group optionally comprising one to four oxygen, sulphur or nitrogen atoms, provided that no heteroatom is directly connected to the CO group; or
ii) a group of formula R 1′ (CO—COOR 2 ) n wherein R 2 has the same meaning as below and R 1′ is a C 2-10 hydrocarbon group, optionally comprising one or two oxygen or nitrogen atoms, provided that no heteroatom is directly connected to the CO group, wherein R 1′ is linked to the keto functional group of the α-ketoacid or α-ketoester and wherein n is an integer comprised between 1 and 4;

and wherein R 2 represents either a hydrogen atom or an alkaline metal ion, or a primary or secondary group which is:
a) a C 1-4 hydrocarbon group optionally comprising one or two oxygen or nitrogen atoms; or
b) a C 5-22 hydrocarbon group optionally comprising one to ten oxygen atoms or one to two nitrogen atoms; provided that said C 5-22 hydrocarbon group is such as that the corresponding aldehyde or ketone of the O—R 2 moiety is an odorless compound; or
c) a group of formula R 2′ (OOC—CO—R 1 ), wherein R 1 has the same meaning as above and R 2′ is a C 2-12 hydrocarbon group optionally comprising one to six oxygen atoms and wherein R 2′ is linked to the ester functional group of the α-ketoester, and wherein n is an integer comprised between 1 and 4;

provided that at least one of R 1 or R 2 is a group as

Assignees

• Firmenich & Cie

Inventors

• Herrmann Andreas
• Berthier Damien
• Paret Nicolas
• Trachsel Alain

Classifications

• C11D17/0039

  Coated compositions or coated components in the compositions, (micro)capsules · CPC title

• C11D3/507 Primary

  Compounds releasing perfumes by thermal or chemical activation · CPC title

• C11D3/505

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

• A61K2800/56

  Compounds, absorbed onto or entrapped into a solid carrier, e.g. encapsulated perfumes, inclusion compounds, sustained release forms · CPC title

• A61K8/365

  Hydroxycarboxylic acids; Ketocarboxylic acids · CPC title