Photolabile pro-fragrances

Patent metadata

Field	Value
Publication number	US-2016347704-A1
Application number	US-201615232125-A
Country	US
Kind code	A1
Filing date	Aug 9, 2016
Priority date	Feb 24, 2014
Publication date	Dec 1, 2016
Grant date	—

Abstract

The invention relates to specific ketones of formula (I) which act as photolabile pro-fragrances. The invention further relates to detergents or cleaning agents, cosmetic agents and air freshening products including ketones of said type. The invention also relates to a method for lastingly scenting surfaces and a method for lastingly fragrancing rooms using said ketones.

First claim

What is claimed is:

1 . A compound of general formula (I)

wherein
R is a substituted hydrocarbon group, preferably having 2 to 20 C atoms, which has at least one C═O group or an ester group, preferably a C═O group;
R1 is —COX;
R2 is hydrogen, a halogen atom, an aryl group, —NO 2 , a linear or branched, substituted or unsubstituted alkoxy group having up to 15 C atoms, or a linear or branched, substituted or unsubstituted alkenyl group having up to 15 C atoms, or a linear or branched or substituted or unsubstituted alkyl group having up to 15 C atoms;
R3, R4, R5, R6 and R7, independently of one another, are hydrogen, a halogen atom, an amino group, —NO 2 , —NH alkyl, —N(alkyl) 2 , a linear or branched, substituted or unsubstituted alkoxy group having up to 15 C atoms, or a linear or branched, substituted or unsubstituted alkyl group having up to 15 C atoms, a cycloalkyl group, an acyl group, an aryl group, —OH, —COY group, or a quaternary ammonium group of formula (II)

X is H, —R11, —OR11, —NR11R12, —SR11 or halogen, preferably is —OR11;
Y is hydrogen, alkyl, cycloalkyl, aryl, acyl, —OH, —Oalkyl, —NH 2 , NH-alkyl, —N(alkyl) 2 or halogen,
A is a CH 2 group or a CH 2 CH 2 O group with n=1 to 20;
B is oxygen with m=0 or 1, wherein m=0 when A is a CH 2 CH 2 O group;
R8, R9 and R10, independently of one another, are H or a substituted or unsubstituted group including alkyl, cycloalkyl, alkenyl, aryl or acyl groups, and wherein two of the groups R8, R9 and R10 can be interconnected by ring closure; and
R11 and R12, independently of one another, are hydrogen, a linear or branched, substituted or unsubstituted alkyl, aryl, alkylaryl, arylalkyl or alkenyl group, which can all optionally contain heteroatoms, preferably 1-3 heteroatoms selected from N, O and S, and preferably are a (CH(R13)CH(R14)O) p —R15 group with p=1-20 and wherein R13, R14 and R15, independently of one another, are hydrogen, or a linear or branched, substituted or unsubstituted alkyl group.

2 . The compound according to claim 1 , wherein R2 is a linear or branched, substituted or unsubstituted alkyl group having up to 6 C atoms.

3 . The compound according to claim 1 , wherein R2 is a linear or branched, substituted or unsubstituted alkyl group having 3 C atoms.

4 . The compound according to claim 1 , wherein R2 is a methyl group.

5 . The compound according to claim 1 , wherein R3, R4, R5, R6 and/or R7 denote hydrogen.

6 . The compound according to claim 1 , wherein R3, R4, R5, R6 and R7 denote hydrogen.

7 . The compound according to claim 1 , wherein the compound of formula I corresponds to the formula (III)

wherein
R16 is a hydrocarbon group having at least 5 C atoms, which in particular comprises a cyclic, optionally substituted hydrocarbon group, preferably a cyclic, substituted alkenyl group, in particular

X is H, —R11, —OR11, —NR11R12, —SR11 or halogen, preferably is —OR11; and
R11 and R12, independently of one another, are hydrogen, a linear or branched, substituted or unsubstituted alkyl or alkenyl group having up to 20 C atoms, an aryl group having 6 to 14 C atoms, alkylaryl or arylalkyl group, wherein alkyl and aryl are as defined above, and preferably are a linear or branched, unsubstituted alkyl group having up to 16 C atoms, or are a (CH(R13)CH(R14)O) p R15 group with p=1-20 and R13, R14 and R15, independently of one another, are hydrogen, or a linear or branched, substituted or unsubstituted alkyl group, preferably are a (CH(R13)CH(R14)O) p R15 group with p=1-10 and R13, R14 and R15, independently of one another, are hydrogen, methyl or ethyl.

8 . The compound according to claim 7 , wherein the compound of formula III is selected from the group consisting of (IV) to (X):

9 . A detergent or cleaning agent, comprising at least one compound of claim 1 .

10 . A detergent or cleaning agent according to claim 9 , wherein the compound of claim 1 comprises 0.0001 and 5% by weight of the total agent.

11 . A detergent or cleaning agent according to claim 9 , wherein the compound of claim 1 , comprises between 0.01 and 3% by weight of the total agent.

12 . The detergent or cleaning agent according to claim 9 , wherein it further comprises
(1) it includes at least one surfactant, selected from the group consisting of anionic, cationic, non-ionic, zwitterionic or amphoteric surfactants, or mixtures thereof; and/or (2) the detergent or cleaning agent is in solid or liquid form.

13 . An air freshening product, comprising at least one compound of claim 1 .

14 . An air freshening product according to claim 13 , wherein the compound of claim 1 comprises 0.0001 and 50% by weight of the total product.

15 . An air freshening product according to claim 13 , wherein the compound of claim 1 comprises 0.01 and 3% by weight of the total product.

16 . A cosmetic agent, comprising at least one compound of claim 1 .

17 . A cosmetic agent according to claim 16 , wherein the compound of claim 1 comprises 0.0001 and 5% by weight of the total agent.

18 . A cosmetic agent according to claim 16 , wherein the compound of claim 1 comprises 0.01 and 3% by weight of the total agent.

19 . A method for lastingly scenting surfaces, comprising, applying to a surface a compound according to claim 1 and exposing the surface to an electromagnetic radiation comprising the wavelengths from 200 to 600 nm.

Assignees

• Henkel Ag & Co Kgaa

Inventors

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

Classifications

• A61K8/37 Primary

  Esters of carboxylic acids · CPC title

• C11D3/50

  Perfumes · CPC title

• A61Q19/10

  Washing or bathing preparations · CPC title

• C07C2101/14

  Chemistry & Metallurgy · mapped topic

• C11B9/0061

  compounds containing a six-membered aromatic ring not condensed with another ring · CPC title