Photolabile pro-fragrances

Patent metadata

Field	Value
Publication number	US-10235708-B2
Application number	US-201213586113-A
Country	US
Kind code	B2
Filing date	Aug 15, 2012
Priority date	Feb 17, 2010
Publication date	Mar 19, 2019
Grant date	Mar 19, 2019

Abstract

Photolabile scent storage substance that are capable of photoinduced release of cyclic compounds have at least one cyclic double bond. These scent storage substances are special ketones, and enable greatly improved stability of the scent impression, in particular with a fresh character, in typical applications, for example in textile laundering, room scenting, and in the cosmetic sector. More economical utilization of the stored scents can thereby be ensured. Also described are corresponding washing or cleaning agents, scenting methods, and methods for manufacturing the special ketones.

First claim

What is claimed is:

1. A washing or cleaning agent comprising at least one ketone of the general formula (I) in quantities of between 0.0001 and 5 wt. %, based on the total agent:

where i=1 or 2,
R3, R4, R5, R6, and R7, mutually independently, denote hydrogen, a halogen atom, NO 2 , a linear or branched, substituted or unsubstituted alkoxy group having 1 to 15 carbon atoms, or a linear or branched, substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, and
R1 and R2, mutually independently, denote a secondary, tertiary, or quaternary carbon atom, and
Q denotes at least one divalent substituted or unsubstituted group bridging R1 and R2 and having 1 to 10 carbon atoms.

2. The washing or cleaning agent according to claim 1 , wherein i=2 and Q comprises at least one bridging group encompassing 2 to 6 carbon atoms.

3. The washing or cleaning agent according to claim 1 , wherein one or more of R1, R2, and at least one divalent group Q bridging R1 and R2 comprises a substitution with at least one heteroatom selected from the group consisting of N, O, or S.

4. The washing or cleaning agent according to claim 1 , wherein four of the five aryl substituents R3, R4, R5, R6, and R7 denote hydrogen.

5. The washing or cleaning agent according to claim 1 , wherein by cleavage of a carbon bond, a ketone of the general formula (II)

and a compound of the general formula (III)

are formable.

6. The washing or cleaning agent according to claim 5 , wherein the compound of the general formula (III) in claim 5 is a cyclic terpene or cyclic terpenoid having at least one cyclic double bond.

7. The washing or cleaning agent according to claim 6 , wherein the cyclic terpene or cyclic terpenoid is selected from the group consisting of α-pinene, α-terpinene, limonene, β-bisabolene, humulene, terpinolene, phellandrene, trichodiene, and from enantiomers and/or diastereomers thereof.

8. A method for long-lasting scenting of surfaces, comprising:
applying the washing or cleaning agent according to claim 1 onto the surface to be scented, and
exposing said surface to an electromagnetic radiation encompassing the wavelengths from 200 to 400 nm.

9. The method according to claim 8 , wherein the step of applying the washing or cleaning agent onto the surface to be scented comprises applying a washing or cleaning agent comprising the ketone onto the surface to be scented.

10. A method for manufacturing the ketone of the general formula (I) in accordance with claim 1 , comprising:
a) hydroborating a compound of the general formula (III)

where i=1 or 2, and R1 and R2, mutually independently, denote a secondary, tertiary, or quaternary carbon atom and Q denotes at least one divalent substituted or unsubstituted group bridging R1 and R2 and having 1 to 10 carbon atoms,

b) reacting the organoborane adduct produced in step a) with a compound of the general formula (IV)

where X is a halogen atom and R3, R4, R5, R6, and R7, mutually independently, denote hydrogen, a halogen atom, NO 2 , a linear or branched, substituted or unsubstituted alkoxy group having 1 to 15 carbon atoms, or a linear or branched, substituted or unsubstituted alkyl group having 1 to 15 carbon atoms.

Assignees

• Gerke Thomas
• Kropf Christian
• Huchel Ursula
• Griesbeck Axel
• Hinze Olga
• Henkel Ag & Co Kgaa

Inventors

• Gerke Thomas
• Kropf Christian
• Huchel Ursula
• Griesbeck Axel
• Hinze Olga

Classifications

• G06Q30/0635 Primary

  replenishment orders; recurring orders · CPC title

• C11D3/2072

  Aldehydes-ketones · CPC title

• C11D3/507

  Compounds releasing perfumes by thermal or chemical activation · CPC title

• C07C45/68

  by increase in the number of carbon atoms · CPC title

• A61Q17/04

  Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations · CPC title