Stabilized perfume oils

Patent metadata

Field	Value
Publication number	US-9845449-B2
Application number	US-201213585926-A
Country	US
Kind code	B2
Filing date	Aug 15, 2012
Priority date	Feb 18, 2010
Publication date	Dec 19, 2017
Grant date	Dec 19, 2017

Abstract

Stable formulations and perfume compositions include amino alcohol(s) as well as >10 wt % fragrances.

First claim

What is claimed is:

1. A perfume composition comprising:
one or more fragrance compounds selected from the group of compound classes consisting of terpenoids, pyrocatechol derivatives, phenol derivatives, aromatics, aliphatics, alicycles, and heterocycles;
amino alcohol(s) according to the formula (II)

wherein R 1 , R 2 , and R 3 in formula (II), mutually independently in each case, denote hydrogen or hydrocarbon residues, or hydroxyalkyl residues in which the hydrocarbon or hydroxyalkyl residues are optionally substituted; and
optionally one or more solvents selected from the group consisting of benzyl alcohol, dipropylene glycol, Dowanol, ethanol, isopropanol, isopropyl myristate, paraffin, propylene glycol, castor oil, and triazine,
wherein the fragrance compound(s) and amino alcohol(s) constitute at least 50 wt. % of the perfume composition.

2. The composition according to claim 1 , wherein the formula (II) is selected from the group consisting of 2-aminopropane-1,3-diol, 2-amino-2-(hydroxymethyl)propane-1,3-diol, 2-amino-2-methylpropane-1,3-diol, 2-amino-2-ethylpropane-1,3-diol, and 1-phenyl-2-aminopropane-1,3-diol.

3. The composition according to claim 1 , wherein more than 1 wt % of the fragrance compound(s) contained are selected from those fragrances that carry an aldehyde function (RCH═O), a keto group (RR′C═O), a hydroxy function (—OH), and/or groups having isolated double bonds, the “wt %” indication referring to the total quantity of perfume oils contained in the composition.

4. The composition according to claim 1 , wherein at least one scent aldehyde selected from adoxal, anisaldehyde, cymal, ethyl vanillin, florhydral, helional, heliotropin, hydroxycitronellal, koavon, lauraldehyde, lyral, methylnonylacetaldehyde, P-T-bucinal, phenylacetaldehyde, undecylenealdehyde, vanillin, 2,6,10-trimethyl-9-undecenal, 3-dodecen-1-al, alpha-n-amylcinnamaldehyde, 4-methoxybenzaldehyde, benzaldehyde, 3-(4-tert-butylphenyl)propanal, 2-methyl-3-(para-methoxyphenyl)propanal, 2-methyl-4-(2,6,6-trimethyl-2(l)-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-isopropylbenzylaldehyde, 1,2,3,4,5,6,7,8-octahydro-8,8-dimethyl-2-naphthaldehyde, 2,4-dimethyl-3-cyclohexene-1-carboxaldehyde, 2-methyl-3-(isopropylphenyl)propanal, 1-decanal, decylaldehyde, 2,6-dimethyl-5-heptenal, 4-(tricyclo[5.2.1.0(2,6)]-decylidene-8)-butanal, octahydro-4,7-methane-1H-indenecarboxaldehyde, 3-ethoxy-4-hydroxybenzaldehyde, para-ethyl-alpha,alpha-dimethylhydrocinnamaldebhyde, alpha-methyl-3,4-(methylenedioxy) hydrocinnanmaldehyde, 3,4-methylenedioxybenzaldehyde, alpha-n-hexylcinnam-aldehyde, m-cymene-7-carboxaldehyde, alpha-methylphenylacetaldehyde, 7-hydroxy-3,7-dimethyloctanal, undecenal, 2,4,6-trimethyl-3-cyclohexene-1-carboxaldehyde, 4-(3)(4-methyl-3-pentenyl)-3-cyclohexenecarboxaldehyde, 1-dodecanal, 2,4-dimethylcyclohexene-3-carboxaldehyde, 4-(4-hydroxy-4-methylpentyl)-3-cylohexene-1-carboxaldehyde, 7-methoxy-3,7-dimethyloctan-1-al, 2-methylundecanal, 2-methyldecanal, 1-nonanal, 1-octanal, 2,6,10-trimethyl-5,9-undecadienal, 2-methyl-3-(4-tert-butyl)propanal, dihydrocinnamaldehyde, 1-methyl-4-(4-methyl-3-pentenyl)-3-cyclohexene-1-carboxaldehyde, 5- or 6-methoxyhexahydro-4,7-methane indane-1- or -2-carboxaldehyde, 3,7-dimethyloctan−1-al, 1-undecanal, 10-undecen−1-al, 4-hydroxy-3-methoxybenzaldehyde, 1-methyl-3-(4-methylpentyl)-3-cyclohexenecarboxaldehyde, 7-hydroxy-3,7-dimethyloctanal, trans-4-decenal, 2,6-nonadienal, para-tolylacetaldehyde, 4-methylphenylacetaldehyde, 2-methyl-4-(2,6,6-trimethyl−1-cyclohexen-1-yl)-2-butenal, ortho-methoxycinnamaldehyde, 3,5,6-trimethyl-3-cyclohexenecarboxaldehyde, 3,7-dimethyl-2-methylene-6-octenal, phenoxyacetaldehyde, 5,9-dimethyl-4,8-decadicnal, peony aldehyde (6,10-dimethyl-3-oxa-5,9-undecadicn-1-al), hexahydro-4,7-methane indane-1-carboxaldehyde, 2-methyloctanal, alpha-methyl-4-(1-methylethyl)benzeneacetaldehyde, 6,6-dimethyl-2-norpinene-2-propionaldehyde, para-methylphenoxyacetaldehyde, 2-methyl-3-phenyl-2-propen−1-al, 3,5,5-trimethylhexanal, hexahydro-8,8-dimethyl-2-naphthaldehyde, 3-propylbicyclo[2.2.1]-hept-5-ene-2-carbaldehyde, 9-decenal, 3-methyl-5-phenyl-1-pentanal, methylnonylacetaldehyde, hexanal, trans-2-hexenal, 1-p-menthene-q-carboxaldehyde, or mixtures thereof, is contained as the fragrance compound(s).

5. The composition according to claim 1 , wherein at least one scent ketone, selected from Buccoxime; isojasmone; methyl-beta-naphthylketone; musk indanone; Tonalid/Musk plus; alpha-damascone, beta-damascone, delta-damascone, isodamascone, damascenone, damarose, methyldihydrojasmonate, menthone, carvone, camphor, fenchone, alpha-ionone, beta-ionone, gamma-methyl (so-called) ionone, fleuramone, dihydrojasmone, cis-jasmone, iso-E-Super®, methylcedrenyl ketone or methyl cedrylone, acetophenone, methylacetophenone, para-methoxyacetophenone, methyl-beta-naphtyl ketone, benzylacetone, benzophenone, para-hydroxyphenylbutanone, celery ketone or livescone, 6-isopropyldecahydro-2-naphthone, dimethyloctenone, frescomenthe, 4-(1-ethoxyvinyl)-3,3,5,5-tetramethylcyclohexanone, methylheptenone, 2-(2-(4-methyl-3-cyclohexen-1-yl)propyl)cyclopentanone, 1-(p-menthen-6(2)yl)-1-propanone, 4-(4-hydroxy-3-methoxyphenyl)-2-butanone, 2-acetyl-3,3-dimethylnorbornane, 6,7-dihydro-1,1,2,3,3-pentamethyl-4(5H)indanone, 4-damascol, dulcinyl or cassione, gelsone, hexalone, isocyclemone E, methylcyclocitrone, methyl lavender ketone, orivone, para-tertiary butylcyclohexanone, verdone, deiphone, muscone, neobutenone, plicatone, veloutone, 2,44,7-tetramethyloct-6-en-3-one, tetrameran, or mixtures thereof, is contained as the fragrance compound(s).

6. The composition according to claim 1 , wherein the amino alcohol is included in quantities from 0.001 to 30 wt %.

7. The composition according to claim 1 , wherein the composition further comprises <15 wt % surfactants.

8. A method for manufacturing perfumed consumer product(s), comprising:
adding a perfume composition according to claim 1 to the consumer product(s).

9. A method for stabilizing one or more fragrance compounds, comprising
adding amino alcohol(s) according to the formula (III)

wherein R 1 , R 2 , and R 3 in formula (I), mutually independently in each case, denote hydrogen or hydrocarbon residues, or hydroxyalkyl residues in which the hydrocarbon or hydroxyalkyl residues are optionally substituted to a perfume composition comprising one or more fragrance compounds selected from the group of compound classes consisting of terpenoids, pyrocatechol derivatives, phenol derivatives, aromatics, aliphatics, alicycles, and heterocycles,
wherein the perfume composition optionally comprises one or more solvents selected from the group consisting of benzyl alcohol, dipropylene glycol, Dowanol, ethanol, isopropanol, isopropyl myristate, paraffin, propylene glycol, castor oil, and triazine, and
wherein the fragrance compound(s) and amino alcohol(s) constitute at least 50 wt. % of the perfume composition.

Assignees

• Huchel Ursula
• Gerigk Andreas
• Smyrek Hubert
• Bunn Ralf
• Bauer Andreas
• Materne Manuela
• Weyhe Marc
• Intemann Klaus
• Preis-Amberger Dagmar
• Henkel Ag & Co Kgaa

Inventors

• Huchel Ursula
• Gerigk Andreas
• Smyrek Hubert
• Bunn Ralf
• Bauer Andreas
• Materne Manuela
• Weyhe Marc
• Intemann Klaus
• Preis-Amberger Dagmar

Classifications

• A61Q13/00

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

• A61L9/01

  Deodorant compositions {(compositions released by contact with a liquid A61L9/05)} · CPC title

• A61K8/41

  Amines · CPC title

• C11D3/50 Primary

  Perfumes · CPC title

• A61L9/04

  using substances evaporated in the air without heating · CPC title