# US 2019/0169529 A1 · Photolabile acetal and ketal compounds for the controlled release of active volatile carbonyl compounds

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 2019/0169529 A1
- Document ID: US20190169529A1
- Status: Published application
- Kind: A1
- Application number: 16/272,504
- Filed: 2019-02-11
- Published: 2019-06-06
- Earliest claimed: 2015-01-21
- Assignees: Firmenich SA
- Applicants: Firmenich SA
- Inventors: Andreas HERRMANN
- Web page: https://patentgrep.com/patent/US20190169529A1

## CPC

- C11B 9/0003: {Compounds of unspecified constitution defined by the chemical reaction for their preparation}
- C07D 319/08: condensed with carbocyclic rings or ring systems
- C11B 9/0015: {containing oxygen as the only heteroatom}
- C11D 3/001: {Softening compositions}
- C11D 3/50: Perfumes
- C11B: PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES (drying-oils C09F)
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C11D: DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL

## Abstract

A method for releasing one or more active volatile aldehydes or ketones from a delivery system based on photosensitive acetal or ketal compounds capable of liberating upon exposure to light an active volatile carbonyl compound in a controlled manner from a surface into the surrounding environment. The delivery system can be used to release active substances such as flavors, fragrances, malodor counteractants, insect attractants or insect repellents. The invention also relates to the use of such acetal or ketal compounds in perfumery, as well as in perfuming compositions or perfumed consumer articles.

## Claims

### Claim 1

A method for releasing one or more active volatile aldehydes or ketones which comprises:
providing a delivery system that includes a compound of formula
wherein
R1 and R2 represent simultaneously or independently a hydrogen atom, a C1-18 hydrocarbon group or a C1-18 group that includes one to three oxygen atoms, one to two nitrogen atoms, and/or one sulfur atom, provided that at least one or both of R1 and R2 includes one of the C1-18 groups; wherein R1 and R2 are derived from an active aldehyde or ketone of formula (R1)(R2)C(═O); said aldehyde or ketone having a molecular weight comprised between 80 and 230 g/mol and being a C5-18 compound;
R3 represent simultaneously or independently from each other, a hydrogen atom, a linear C1-C8 alkyl group, a branched or cyclic C3-C8 alkyl group, a hydroxy group, a methoxy group, an ethoxy group, a 2-hydroxyethoxy group, a 2-ethoxyethoxy group, a (OCH2CH2)nOH group, a (OCH2CH2)nOCH3 group, a methylthio group, a dimethylamino group, or a diethylamino group, with n being an integer varying between 2 and 8; and
R4 and R5 represent, simultaneously or independently from each other, a hydrogen atom, a linear C1-C4 alkyl group, a branched C3-C4 alkyl group, a methoxy group, an ethoxy group, a 2-hydroxyethoxy group, a 2-ethoxyethoxy group, a (OCH2CH2)nOH group, a (OCH2CH2)nOCH3 group, a methylthio group, a dimethylamino group, or a diethylamino group, with n having the same meaning as above, wherein at least one R4 and at least one R5 are a dimethylamino group; and
triggering the release of the one or more active volatile aldehyde or ketone by light.

### Claim 2 (depends on 1)

The method of claim 1, wherein at least two R4 and/or at least two R5 are hydrogen atoms.

### Claim 3 (depends on 1)

The method of claim 1, wherein all of the groups R4 and R5, which are not a hydrogen atom, represent the same group selected from the group consisting of a linear C1-C4 alkyl group, a branched C3-C4 alkyl group, a methoxy group, an ethoxy group, a (OCH2CH2)nOH group, a (OCH2CH2)nOCH3 group, a methylthio group, a dimethylamino group, and a diethylamino group with n being an integer varying between 2 and 8.

### Claim 4 (depends on 1)

The method of claim 1, wherein the R4 and R5 group in ortho position with respect to the bond between the aromatic ring and the oxygenated ring are hydrogen atoms.

### Claim 5 (depends on 1)

The method of claim 1, wherein R4 and R5 are a hydrogen atom, a methoxy group or a dimethylamino group.

### Claim 6 (depends on 1)

The method of claim 1, wherein R3 represents a hydrogen atom, a linear or branched C1-C4 alkyl group, a methoxy group, a dimethylamino group or a diethylamino group.

### Claim 7 (depends on 1)

The method of claim 1, wherein the active volatile aldehyde or ketone is a perfuming ingredient.

### Claim 8 (depends on 1)

The method of claim 1, wherein R4 and R5 represent, simultaneously or independently, from each other, a hydrogen atom, or a methylthio group, with at least one R4 or R5 being a methylthio group.

### Claim 9 (depends on 9)

The method of claim 9, wherein the R4 and R5 groups in ortho position with respect to the bond between the aromatic ring and the oxygenated ring are hydrogen atoms, or wherein the R4 and R5 groups in ortho and para position with respect to the bond between the aromatic ring and the oxygenated ring are hydrogen atoms.

### Claim 10 (depends on 1)

The method of claim 1, wherein the release of the perfuming compounds, is triggered by light at a wavelength above 280, above 300 nm, or above 330 nm.

### Claim 11 (depends on 1)

A perfuming composition comprising
i) at least one compound of formula (I), 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.

### Claim 12 (depends on 1)

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

### Claim 13 (depends on 12)

The perfuming consumer product of claim 12, wherein the perfumery consumer product is a perfume, a fabric care product, a body-care product, an air care product, a home care product or a car care product.

### Claim 14 (depends on 12)

The perfuming consumer product of claim 12, wherein the perfumery consumer product is a fine perfume, a cologne, an after-shave lotion, a liquid or solid detergent, a unidose detergent, a fabric softener, a fabric refresher, an ironing water, a paper, a bleach, a carpet cleaner, a curtain-care product, a shampoo, a conditioner, a coloring preparation, a color care product, a hair shaping product, a hair spray, a skin cream or lotion, 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, a leather care product, a hard-surface detergent, a polish, a wax or a plastic cleaner.