Combination of an amino alcohol, a fragrance and a silicic acid ester, and the use of same as a pro-fragrance

Patent metadata

Field	Value
Publication number	US-9587206-B2
Application number	US-201414327795-A
Country	US
Kind code	B2
Filing date	Jul 10, 2014
Priority date	Feb 1, 2012
Publication date	Mar 7, 2017
Grant date	Mar 7, 2017

Abstract

The invention relates to a composition of (a) a selected amino alcohol compound of general formula (I), (b) a scent aldehyde and/or scent ketone, and (c) a selected silicic acid ester, to the use of same as a pro-scent, as well as to washing and cleaning agents, fabric softeners and cosmetics which contain these. The invention also relates to a method for prolonging the perception of scent in such agents, and to a method for removing malodors by applying said composition.

First claim

What is claimed is:

1. A composition for providing the delayed release of scent comprising:
(a) an amino alcohol compound of the general Formula (I)

wherein R 5 , R 6 , R 7 independently of each other stand for H or a hydrocarbon group that can be acyclic or cyclic, substituted or unsubstituted, branched or unbranched as well as saturated or unsaturated,
or mixtures of these compounds,
(b) a scent aldehyde and/or scent ketone and
(c) a silicic acid ester of the general Formula (II):

wherein all R, independently of each other, are selected from the group that comprises H, the linear or branched, saturated or unsaturated, substituted or unsubstituted C 1 - 6 hydrocarbon groups and scent alcohol residues, and n assumes values in the range 2 to 100, wherein the silicic acid ester at least partially comprises scent alcohol residues.

2. The composition according to claim 1 , wherein the scent aldehyde and/or the scent ketone reacts at least partially under cyclization with the amino alcohol compound of the general Formula (I) to form a 1-aza-3,7-dioxabicyclo [3.3.0]octane compound of the general Formula (III)

wherein R 1 , R 2 , R 3 , R 4 independently of each other stand for residues that in a compound of the general Formula R 1 —C(═O)—R 2 or R 3 —C(═O)—R 4 form a scent aldehyde containing at least 6 carbon atoms or a scent ketone containing at least 6 carbon atoms.

3. The composition according to claim 2 , wherein R 2 , R 4 , R 5 , R 6 , R 7 mean hydrogen and R 1 and R 3 each mean a C 5-24 hydrocarbon residue.

4. The composition according to claim 1 , wherein the scent aldehyde and the scent ketone are selected from the jasmones, ionones, damascones and damascenones, menthone, carvone, iso-E-super, methylheptenone, melonal, cymal, ethyl vanillin, helional, hydroxycitronellal, koavone, methylnonylacetaldehyde, phenylacetaldehyde, undecylenaldehyde, 3-dodecen-1-al, alpha-n-amylcinnamaldehyde, benzaldehyde, 3-(4-tert-butylphenyl)-propanal, 2-methyl-3-(para-methoxyphenylpropanal), 2-methyl-4-(2,6,6-trimethyl-2(1)-cyclohexen-1-yl)butanal, 3-phenyl-2-propenal, cis/trans-3,7-dimethyl-2,6-octadien-1-al, 3,7-dimethyl-6-octen-1-al, [(3,7-dimethyl-6-octenyl)oxy]acetaldehyde, 4-isopropylbenzyaldehyde, 2,4-dimethyl-3-cyclohexene-1-carboxyaldehyde, 2-methyl-3-(isopropylphenyl)propanal, decylaldehyde, 2,6-dimethyl-5-heptenal, alpha-n-hexylcinnamaldehyde, 7-hydroxy-3,7-dimethyloctanal, undecenal, 2,4,6-trimethyl-3-cyclohexene-1-carboxaldehyde, 1-dodecanal, 2,4-dimethylcyclohexene-3-carboxaldehyde, 4-(4-hydroxy-4-methylpentyl)-3-cylohexene-1-carboxaldehyd, 2-methylundecanal, 2-methyldecanal, 1-nonanal, 1-octanal, 2,6,10-trimethyl-5,9-undecadienal, 2-methyl-3-(4-tert-butyl)propanal, dihydrocinnamaldehyde, 3,7-dimethyloctan-1-al, 1-undecanal, 10-undecen-1-al, 4-hydroxy-3-methoxybenzaldehyde, trans-4-decenal, 2,6-nonadienal, para-tolylacetaldehyde, 3,7-dimethyl-2-methylene-6-octenal, 2-methyloctanal, alpha-methyl-4-(1-methylethyl)benzeneacetaldehyde, 2-methyl-3-phenyl-2-propen-1-al, 3,5,5-trimethylhexanal, 3-propyl-bicyclo[2.2.1]hept-5-ene-2-carbaldehyde, 9-decenal, 3-methyl-5-phenyl-1-pentanal, methylnonylacetaldehyde, citral, 1-decanal, florhydral, 2,4-dimethyl-3-cyclohexene-1-carboxaldehyde, heliotropin and mixtures thereof.

5. The composition according to claim 1 , wherein the scent aldehyde and/or the scent ketone reacts at least partially under cyclization with the amino alcohol compound of the general Formula (I) to form a compound of the general Formula (IV)

wherein R 1 and R 2 , independently of one another stand for groups that in a compound of the general Formula R 1 —C(═O)—R 2 form a scent aldehyde containing at least 6 carbon atoms or a scent ketone containing at least 6 carbon atoms.

6. The composition according to claim 1 , wherein at least 5 mol % of the R residues of the general Formula (II) are selected from the group methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl.

7. The composition according to claim 1 , wherein at least 10 mol %, of the R residues of the general Formula (II) are selected from the group consisting of the residues of the scent alcohols 10-undecen-1-ol, 2,6-dimethylheptan-2-ol, 2-methylbutanol, 2-methylpentanol, 2-phenoxyethanol, 2-phenylpropanol, 2-tert-butylcyclohexanol, 3,5,5-trimethylcyclohexanol, 3-hexanol, 3-methyl-5-phenylpentanol, 3-octanol, 3-phenylpropanol, 4-heptenol, 4-isopropylcyclohexanol, 4-tert-butylcyclohexanol, 6,8-dimethyl-2-nonanol, 6-nonen-1-ol, 9-decen-1-ol, alpha-methylbenzyl alcohol, alpha-terpineol, amyl salicylate, benzyl alcohol, benzyl salicylate, beta-terpineol, butyl salicylate, citronellol, cyclohexyl salicylate, decanol, dihydromyrcenol, dimethylbenzyl carbinol, dimethylheptanol, dimethyloctanol, ethyl salicylate, ethyl vanillin, eugenol, farnesol, geraniol, heptanol, hexyl salicylate, isoborneol, isoeugenol, isopulegol, linalool, menthol, myrtenol, n-hexanol, nerol, nonanol, octanol, p-menthan-7-ol, phenylethyl alcohol, phenol, phenyl salicylate, tetrahydrogeraniol, tetrahydrolinalool, thymol, trans-2-cis-6-nonadienol, trans-2-nonen-1-ol, trans-2-octenol, undecanol, vanillin, cinnamyl alcohol and mixtures thereof.

8. The composition according to claim 1 , wherein n assumes values in the range 2 to 50.

9. A washing or cleaning agent, fabric softener or cosmetics, comprising:
(a) an amino alcohol compound of the general Formula (I)

wherein R 5 , R 6 , R 7 independently of each other stand for H or a hydrocarbon group that can be acyclic or cyclic, substituted or unsubstituted, branched or unbranched as well as saturated or unsaturated,
or mixtures of these compounds,
(b) a scent aldehyde and/or scent ketone and
(c) a silicic acid ester of the general Formula (II):

wherein all R, independently of each other, are selected from the group that comprises H, the linear or branched, saturated or unsaturated, substituted or unsubstituted C 1-6 hydrocarbon groups and scent alcohol residues, wherein the silicic acid ester at least partially comprises scent alcohol residues, and n assumes values in the range 2 to 100.

10. A method for extending the perceived scent of washing or cleaning agents, fabric softeners or cosmetics or of hard surfaces treated with them, wherein the composition according to claim 1 is added to the washing or cleaning agents, fabric softeners or cosmetics, and wherein the scent is released by hydrolysis.

11. A method for eliminating malodors of worn washing comprising the step of contacting the worn washing with a composition comprising:
(a) an amino alcohol compound of the general Formula (I)

wherein R 5 , R 6 , R 7 independently of each other stand for H or a hydrocarbon group that can be acyclic or cyclic, substituted or unsubstituted, branched or unbranched as well as saturated or unsaturated,
or mixtures of these compounds,
(b) a scent aldehyde and/or scent ketone and

Assignees

• Henkel Ag & Co Kgaa

Inventors

• Bauer Andreas
• Huchel Ursula
• Gerigk Andreas
• Weyhe Marc
• Gerke Thomas
• Smyrek Hubert

Classifications

• C11B9/0015

  containing oxygen as the only heteroatom · CPC title

• C11B9/0003

  Compounds of unspecified constitution defined by the chemical reaction for their preparation · CPC title

• A61K8/41 Primary

  Amines · CPC title

• A61Q19/00

  Preparations for care of the skin · CPC title

• C11D3/507

  Compounds releasing perfumes by thermal or chemical activation · CPC title