Microcapsules containing a gas-generating photolabile polymer and uses thereof

Patent metadata

Field	Value
Publication number	US-10105311-B2
Application number	US-201515528657-A
Country	US
Kind code	B2
Filing date	Nov 23, 2015
Priority date	Nov 24, 2014
Publication date	Oct 23, 2018
Grant date	Oct 23, 2018

Abstract

The present invention relates to water-dispersable microcapsules comprising an oil phase, e.g. a perfume, containing a photolabile polymer comprising α-ketoacid or α-ketoester group 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 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, or consisting of:
an oil phase;
at least one photolabile linear or graft polymer comprising an α-ketoacid or α-ketoester group capable of generating, upon exposure to light a gas selected among the group consisting of CO and CO 2 and comprising at least one unit of formula

wherein said unit of formula (I) comprises a benzenediyl functional group substituted in meta or para and is part of:
a) a backbone of a linear polymer of formula

wherein n represents an integer varying between 2 and 1000, R 1 represents a C 1-8 hydrocarbon group and R 2 represents a hydrogen atom or a methyl group; or
b) a side chain of a graft polymer of formula

wherein
M represents a C 1-8 aliphatic hydrocarbon group optionally comprising one or two oxygen atoms and/or one nitrogen atom;
P represents a OR 3 ; a COOR 3 group, a COOCH 2 C 6 H 5 group, a COOC 6 H 5 group, a C 6 H 5 group, a C 6 H 4 COOR 3 group, a C 6 H 4 OH group, a OC(═O)R 3 group, a CON(R 3 ) 2 , a 2-oxopyrrolidin-1-yl or a 2-oxoazepan-1-yl wherein R 3 represents a hydrogen atom, a C 1-18 alkyl group, a (CH 2 CH 2 ) 1-3 OH group;
L is a hydrogen atom or a methyl group;
X represents the unit of formula (I) provided that the oxygen atom of the carboxyl functional group of the unit (I) is linked to a primary or secondary carbon atom;
R 1 represents a hydrogen atom, a C 1-22 hydrocarbon group optionally comprising one to three oxygen atoms and/or one to two nitrogen atoms and/or one sulfur atom, or, if R 1 is linked to the oxygen atom of the carboxyl functional group of the unit (I), an alkaline metal ion;
p is an integer varying between 5 and 1000;
q is an integer varying between 0 and 500;
r is an integer varying between 0 and 1; and
T is a polymer terminating group;
optionally comprising at least one photo-catalyst; and

B) a shell surrounding said core formed by interfacial polymerization, by a phase separation process induced by polymerization or by coacervation.

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

3. A microcapsule according to claim 1 , wherein R 1 represents a C 1-8 aliphatic hydrocarbon.

4. A microcapsule according to claim 1 , wherein the photolabile polymer is a polymer of formula (III).

5. A microcapsule according to claim 4 , wherein M represents a group of formula

wherein the wavy line indicates the location of the bond between M and X, and the bold line indicates the location of the bond between M and the unit of formula [C(L)CH 2 ] P , and wherein Y represents an oxygen atom, or a carboxyl functional group, R 4 represents C 1-7 aliphatic hydrocarbon group and r is an integer varying between 0 and 1 providing that r is equal to 0 only when Y is a carboxyl functional group.

6. A microcapsule according to claim 4 , wherein R 1 represents a C 2-10 alkyl group optionally comprising one to three oxygen atoms and/or one or two nitrogen atoms.

7. A microcapsule according to claim 6 , wherein the α-ketoacid or α-ketoester group generates a gas upon exposure to light at a wavelength comprised between 450 and 320 nm.

8. A microcapsule according to claim 7 , wherein said microcapsules comprise, based on the total microcapsule weight, from about 10% to about 50% by weight of photolabile polymer.

9. A microcapsule according to claim 1 , wherein said shell surrounding said core is an aminoplast, polyamide, polyester, polyurea or polyurethane resins or a mixture thereof.

10. A microcapsule according to claim 1 , wherein said shell has a thickness varying between 20 and 500 nm.

11. A microcapsule according to claim 1 , wherein the oil phase contains a perfuming oil.

12. A perfuming consumer product comprising:
i) as a perfuming ingredient, at least one microcapsule, defined in claim 11 ; and
ii) optionally a free perfume oil.

13. A perfuming consumer product according to claim 12 , wherein the perfumery consumer product is a perfume, a fabric care product, a body-care product, an air care product or a home care product.

14. A perfuming consumer product according to claim 12 , wherein the perfumery 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.

15. A method for intensifying or prolonging fragrance of a perfume ingredient on a surface, which comprises treating the surface with a microcapsule as defined in claim 11 in the presence of light under conditions which are susceptible of allowing release of the perfume oil.

16. A method for intensifying or prolonging fragrance of a perfume ingredient on a surface, which comprises treating the surface with a perfuming consumer product as defined in claim 12 in the presence of light under conditions which are susceptible of allowing release of the perfume oil.

17. The method of claim 16 wherein the perfumery consumer product is a perfume, a fabric care product, a body-care product, an air care product or a home care product.

18. The method of claim 16 wherein the perfumery 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.

Assignees

• Firmenich & Cie

Inventors

• Herrmann Andreas
• Berthier Damien
• Lamboley Serge
• Paret Nicolas

Classifications

• A61K8/37

  Esters of carboxylic acids · CPC title

• C11D3/507

  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

• A61K8/91 Primary

  Graft copolymers (A61K8/89 takes precedence) · CPC title

• A61K8/85

  Polyesters · CPC title