Photolabile pro-fragrances

Patent metadata

Field	Value
Publication number	US-9730875-B2
Application number	US-201615012227-A
Country	US
Kind code	B2
Filing date	Feb 1, 2016
Priority date	Jun 22, 2012
Publication date	Aug 15, 2017
Grant date	Aug 15, 2017

Abstract

Fragrances that provide a scent of freshness tend to be volatile and are therefore not very economical when used in typical applications such as washing or cleaning processes, so they have to be used in relatively large quantities to be able to produce adequate effects. The disclosed photolabile pro-fragrances provide a much longer-lasting sense of fragrance, in particular with a scent of freshness, when used in typical applications, thus allowing said fragrances to be used economically.

First claim

What is claimed is:

1. A washing or cleaning agent containing at least one compound of the general formula (I),

wherein R denotes a substituted hydrocarbon residue with 2 to 20 C atoms, having at least one carbonyl group or ester group,
R1, R2 each, independently of one another, denote hydrogen, a linear or branched, substituted or unsubstituted alkoxy group with 1 to 15 C atoms, a linear or branched, substituted or unsubstituted alkyl group or alkenyl group with 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, —NO 2 , a linear or branched, substituted or unsubstituted alkoxy group with 1 to 15 C atoms, a linear or branched, substituted or unsubstituted alkyl group with 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 quaternary ammonium residue of formula (II),

wherein
A denotes a CH 2 or a CH 2 CH 2 O group with n=1 to 20 and
B denotes oxygen with m=0 or 1, wherein m=0 if A is a CH 2 CH 2 O group and R8, R9, R10 each, independently of one another, denote H or a substituted or unsubstituted, alkyl, cycloalkyl, alkenyl, aryl or acyl group-containing residue, and wherein two of the residues R8, R9, R10 can in each case be joined together by ring closure.

2. The washing or cleaning agent according to claim 1 , wherein the substituents R1 and R2, independently of one another, denote a linear or branched, substituted or unsubstituted alkyl group with 1 to 6 C atoms, preferably 1 to 3 C atoms, in particular in each case a methyl residue.

3. The washing or cleaning agent according to claim 1 , wherein substituents R3, R4, R6 and R7 each denote hydrogen, and wherein the residue R5 denotes a quaternary ammonium residue of formula (II),

wherein
A denotes a CH 2 or a CH 2 CH 2 O group with n=1 to 20 and
B denotes oxygen with m=0 or 1, wherein m=0 if A is a CH 2 CH 2 O group and R8, R9, R10 each, independently of one another, denote H or a substituted or unsubstituted, alkyl, cycloalkyl, alkenyl, aryl or acyl group-containing residue, and wherein two of the residues R8, R9, R10 can in each case be joined together by ring closure.

4. The washing or cleaning agent according to claim 1 , wherein R denotes a substituted hydrocarbon residue with 2 to 20 C atoms, which has at least one ester group, and R2 denotes a substituted or unsubstituted aryl residue.

5. The washing or cleaning agent according to claim 1 , wherein R denotes a substituted hydrocarbon residue with 2 to 20 C atoms and R2 denotes a linear or branched, substituted or unsubstituted alkyl group or alkenyl group with 1 to 15 C atoms.

6. The washing or cleaning agent according to claim 1 , wherein R denotes a substituted hydrocarbon residue with 2 to 20 C atoms substituted with a cyclic alkenyl residue that has at least one carbonyl group and R2 denotes a linear or branched an alkyl group with 1, 2 or 3 C atoms.

7. The washing or cleaning agent according to claim 1 , wherein the compound corresponds to one of the following formulae (III) to (X)

8. The washing or cleaning agent according to claim 1 , wherein the compound comprises 0.0001 to 5 wt. % of the total washing or cleaning agent.

9. The washing or cleaning agent according to claim 1 , wherein the compound comprises 0.001 to 4 wt. % of the total washing or cleaning agent.

10. The washing or cleaning agent according to claim 1 , wherein the compound comprises 0.01 and 3 wt. % of the total washing or cleaning agent.

11. The washing or cleaning agent according to claim 1 , wherein the compound comprises 0.1 and 2 wt. % of the total washing or cleaning agent.

12. The washing or cleaning agent according to claim 1 , further comprising at least one surfactant selected from the group consisting of anionic, cationic, nonionic, zwitterionic and amphoteric surfactants and mixtures thereof.

Assignees

• Henkel Ag & Co Kgaa

Inventors

• Gerke Thomas
• Kropf Christian
• Huchel Ursula
• Griesbeck Axel
• Landes Agnieszka

Classifications

• C07C217/74

  with rings other than six-membered aromatic rings being part of the carbon skeleton · CPC title

• C07D207/06

  with radicals, containing only hydrogen and carbon atoms, attached to ring carbon atoms · CPC title

• A61Q13/00

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

• A61K8/4913 Primary

  having five membered rings, e.g. pyrrolidone carboxylic acid · CPC title

• C11D3/50

  Perfumes · CPC title