Photolabile pro-fragrances

Patent metadata

Field	Value
Publication number	US-2016186103-A1
Application number	US-201615061053-A
Country	US
Kind code	A1
Filing date	Mar 4, 2016
Priority date	Jun 30, 2011
Publication date	Jun 30, 2016
Grant date	—

Abstract

Fragrances having a fresh character are usually very volatile and therefore not very economical in typical applications such as washing or cleaning processes for example. For that reason they have to be used in relatively large amounts in order to bring about appropriate effects. The present invention describes photolabile pro-fragrances of formula (I) that allow for a greatly improved persistence of the fragrance impression, in particular one having a fresh character, in typical applications. Said pro-fragrances attach very readily to target substrates, such as textiles for example. A more economical use of the fragrances in question can be ensured in this way.

First claim

What is claimed is:

1 . A ketone of the general formula (I),

wherein
R denotes a substituted hydrocarbon residue having at least one C═O group,
R1, R2 each independently of one another denote hydrogen, an aryl residue, a linear or branched, substituted or unsubstituted alkoxy group having 1 to 15 C atoms, a linear or branched, substituted or unsubstituted alkyl group having 1 to 15 C atoms or a substituted or unsubstituted aryl residue,
R3, R4, R5, R6 and R7 each independently of one another denote hydrogen, an amino group, —NO2, a linear or branched, substituted or unsubstituted alkoxy group having 1 to 15 C atoms, a linear or branched, substituted or unsubstituted alkyl group having 1 to 15 C atoms, a cycloalkyl residue, acyl residue, aryl residue, —OH, —NH 2 , halogen, NH alkyl or —N(alkyl) 2 ,
and wherein at least one of the residues R3, R4, R5, R6, R7 denotes a —CO—X group, where X═H, alkyl, cycloalkyl, aryl, acyl, —OH, —Oalkyl, NH 2 , NH-alkyl, —N(alkyl) 2 or halogen.

2 . The ketone according to claim 1 , wherein the substituents R1 and R2, independently of one another, denote a linear or branched, substituted or unsubstituted alkyl group having 1 to 6 C atoms, preferably 1 to 3 C atoms, in particular in each case a methyl residue, wherein R3, R6 and R7 each denote hydrogen, wherein the residues R4 and R5 each independently of one another denote hydrogen or a —CO—X group, where X═H, alkyl, cycloalkyl, aryl, acyl, —OH, —Oalkyl, —NH 2 , NH-alkyl, —N(alkyl) 2 or halogen, and wherein at least one of residues R4 or R5 denoting the —CO—X group.

3 . The ketone according to claim 1 , selected from the group consisting of ketones corresponding to formula (II) or (III)

wherein the residue R8 in each case denotes an optionally substituted hydrocarbon residue having at least 5 C atoms, wherein the residue X in each case denotes H, alkyl, cycloalkyl, aryl, acyl, —OH, —Oalkyl, —NH 2 , NH-alkyl, —N(alkyl) 2 or halogen.

4 . The ketone according to claim 3 , wherein the residue X denotes H or an —Oalkyl group.

5 . A washing or cleaning agent comprising at least one ketone according to claim 1 , wherein said ketone is contained in amounts of between 0.0001 and 5 wt. %, relative to the total agent.

6 . The washing or cleaning agent according to claim 5 , wherein it contains at least one surfactant selected from the group consisting of anionic, cationic, non-ionic, zwitterionic, amphoteric surfactants or mixtures thereof.

7 . The washing or cleaning agent according to claim 5 , wherein it is in solid or liquid form.

8 . A cosmetic agent comprising at least one ketone according to claim 1 , wherein said ketone is contained in amounts of between 0.0001 and 50 wt. %, relative to the total agent.

9 . A method for the lasting fragrancing of surfaces, wherein a ketone according to claim 1 is applied to the surface to be fragranced and said surface is then exposed to electromagnetic radiation.

Assignees

• Henkel Ag & Co Kgaa

Inventors

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

Classifications

• A61K8/368 Primary

  with carboxyl groups directly bound to carbon atoms of aromatic rings · CPC title

• A61Q13/00

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

• C11D3/50 Primary

  Perfumes · CPC title

• C07C69/76

  Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring · CPC title

• C11D3/2072

  Aldehydes-ketones · CPC title