Cleavable surfactant

Patent metadata

Field	Value
Publication number	US-11344493-B2
Application number	US-201816342523-A
Country	US
Kind code	B2
Filing date	Jan 22, 2018
Priority date	Jan 23, 2017
Publication date	May 31, 2022
Grant date	May 31, 2022

Abstract

Cleavable surfactants of formula (I)

having a total hydrophilic-lipophilic balance (HLB) of between 3 and 18 and wherein A is a group capable of releasing a flavor or fragrance aldehyde of formula (R 1 )CHO or a flavor or fragrance ketone of formula (R 1 )(R 2 )CO and is of formula

wherein the wavy line indicates the location of the bond between L and A; R 1 and R 2 represent a hydrogen atom or a saturated or unsaturated C 1 -C 18 hydrocarbon group, provided that at least one of the R 1 or R 2 groups has 6 consecutive carbon atoms and that both R 1 and R 2 taken together comprise a maximum of 18 carbon atoms; and L is a linear, branched or cyclic, saturated or unsaturated C 3 to C 40 hydrocarbon group. These surfactants solubilize and/or stabilize flavor and fragrance aldehydes and ketones in an aqueous environment and at the same time to control their release by hydrolysis.

First claim

What is claimed is:

1. A compound of formula

having a total hydrophilic-lipophilic balance comprised between 3 and 18 being calculated using the Effective Chain Length model and wherein
A is a group capable of releasing a flavor or fragrance aldehyde of formula (R 1 )CHO or a flavor or fragrance ketone of formula (R 1 )(R 2 )CO and is of formula

wherein the wavy line indicates the location of the bond between L and A; R 1 and R 2 represent independently from each other a hydrogen atom or a linear saturated or unsaturated C 1 -C 18 hydrocarbon group, optionally substituted with one to three oxygen atoms in the form of a hydroxyl, carbonyl, ether or ester group, or a branched or cyclic, saturated or unsaturated C 3 -C 18 hydrocarbon group, optionally substituted with one to three oxygen atoms in the form of a hydroxyl, carbonyl, ether or ester group or R 1 and R 2 , when taken together, represent a C 4-18 linear, branched or cyclic alkanediyl group, optionally substituted with one to three oxygen atoms in the form of a hydroxyl, carbonyl, ether or ester group, provided that at least one of the R 1 or R 2 groups has 6 consecutive carbon atoms and that both R 1 and R 2 taken together comprise a maximum of 18 carbon atoms;
L is a OC 6 H 4 CR 3 2 CR 3 2 group or a (OCH 2 CHR 3 ) q group, wherein R 3 represents a hydrogen atom or a methyl group and q is an integer varying between 3 and 10; and
Q is a polyimine, a poly(ethylene oxide), a poly(propylene oxide), a polypeptide, or a polysaccharide.

2. The compound according to claim 1 , wherein Q represents a poly(ethylene oxide), a poly(propylene oxide), or a polypeptide.

3. The compound according to claim 1 , wherein Q represents a CH 3 (OC 2 H 4 ) m group wherein m is an integer varying between 11 and 30.

4. A solubilizing system comprising water, perfuming or flavoring oil and at least one compound of formula (I) as defined in claim 3 .

5. The solubilizing system according to claim 4 , wherein the solubilizing system comprises water and dispersed perfuming or flavoring ingredient-containing oil droplets which are stabilized by the at least one compound of formula (I).

6. The solubilizing system according to claim 5 , characterized in that the perfuming or flavoring ingredient-containing oil comprises perfuming or flavoring ingredients being an aldehyde of formula R 1 CH(O) or a ketone of formula (R 1 )(R 2 )C(═O) wherein R 1 and R 2 represent independently from each other a hydrogen atom or a linear saturated or unsaturated C 1 -C 18 hydrocarbon group, optionally substituted with one to three oxygen atoms in the form of a hydroxyl, carbonyl, ether or ester group, or a branched or cyclic, saturated or unsaturated C 3 -C 18 hydrocarbon group, optionally substituted with one to three oxygen atoms in the form of a hydroxyl, carbonyl, ether or ester group or R 1 and R 2 , when taken together, represent a C 4-18 linear, branched or cyclic alkanediyl group, optionally substituted with one to three oxygen atoms in the form of a hydroxyl, carbonyl, ether or ester group, provided that at least one of the R 1 or R 2 groups has 6 consecutive carbon atoms and that both R 1 and R 2 taken together comprise a maximum of 18 carbon atoms.

7. A perfuming or flavoring composition comprising:
a) as perfuming or flavoring ingredient, at least one compound of formula (I) as defined in claim 1 ;
b) at least one ingredient selected from the group consisting of a perfumery or flavor carrier, a perfuming or flavoring co-ingredient and mixtures thereof; and
c) optionally at least one perfumery or flavor adjuvant.

8. A perfuming or flavoring consumer product comprising at least one compound of formula (I) as defined in claim 1 .

9. The perfuming consumer product according to claim 8 , wherein the consumer product is a perfuming consumer product comprising a perfume, a fabric care product, a body-care product, a cosmetic preparation, a skin-care product, an air care product or a home care product or the consumer product is a flavoring consumer product comprising a beverage.

10. The perfuming consumer product according to claim 9 , wherein the perfumery consumer product is selected from the group consisting of a fine perfume, a splash or eau de perfume, a cologne, an shave or after-shave lotion, a liquid or solid detergent, a fabric softener, a fabric refresher, an ironing water, a paper, a bleach, a carpet cleaners, curtain-care products a shampoo, a coloring preparation, a color care product, a hair shaping product, a dental care product, a disinfectant, an intimate care product, a hair spray, a vanishing cream, a deodorant or antiperspirant, hair remover, tanning or sun product, nail products, skin cleansing, a makeup, a perfumed soap, shower or bath mousse, oil or gel, or a foot/hand care products, a hygiene product, an air freshener, a “ready to use” powdered air freshener, a mold remover, furnisher care, wipe, a dish detergent or hard-surface detergent, a leather care product, and a car care product.

11. A method for releasing active volatile aldehydes or ketones comprising applying to a composition, an article or a surface an effective amount of at least one compound of formula (I) as defined in claim 1 .

12. A method for solubilizing and/or stabilizing hydrophobic molecules in an aqueous environment comprising adding to said aqueous environment an effective amount of at least one compound of formula (I) as defined in claim 1 .

13. A perfuming or flavoring composition comprising:
a) as perfuming or flavoring ingredient, a solubilizing system as defined in claim 4 ;
b) at least one ingredient selected from the group consisting of a perfumery or flavor carrier, a perfuming or flavoring co-ingredient and mixtures thereof; and
c) optionally at least one perfumery or flavor adjuvant.

14. A perfuming or flavoring consumer product comprising a solubilizing system, as defined in claim 4 .

15. The perfuming consumer product according to claim 14 , wherein the consumer product is a perfuming consumer product comprising a perfume, a fabric care product, a body-care product, a cosmetic preparation, a skin-care product, an air care product or a home care product or the consumer product is a flavoring consumer product comprising a beverage.

16. The perfuming consumer product according to claim 15 , wherein the perfumery consumer product is selected from the group consisting of a fine perfume, a splash or eau de perfume, a cologne, an shave or after-shave lotion, a liquid or solid detergent, a fabric softener, a fabric refresher, an ironing water, a paper, a bleach, a carpet cleaners, curtain-care products a shampoo, a coloring preparation, a color care product, a hair shaping product, a dental care product, a disinfectant, an intimate care product, a hair spray, a vanishing cream, a deodorant or antiperspirant, hair remover, tanning or sun product, nail products, skin cleansing, a makeup, a perfumed soap, shower or bath mousse, oil or gel, or a foot/hand care products, a hygiene product, an air freshener, a “ready to use” powdered air freshener, a mold remover, furnisher care, wipe, a dish detergent or hard-surface detergent, a leather care product, and a car care product.

17. A method for releasing active volatile aldehydes or ketones comprising applying to a composition, an article or a surface an effective amount of the solu

Assignees

• Firmenich & Cie

Inventors

• Lutz Eric
• Giuseppone Nicolas
• Herrmann Andreas
• Tchakalova Vera
• Benczedi Daniel

Classifications

• C08G65/331

  containing oxygen {(cyclic ether compounds C08G65/26)} · CPC title

• A61K2800/49

  Solubiliser, Solubilising system · CPC title

• A61Q13/00

  Formulations or additives for perfume preparations (essential oils or perfumes per se C11B9/00) · CPC title

• C11D1/008

  Polymeric surface-active agents · CPC title

• A23V2002/00

  Food compositions, function of food ingredients or processes for food or foodstuffs · CPC title