Process for controlling malodors using oxazolidines

Patent metadata

Field	Value
Publication number	US-9862727-B2
Application number	US-201414179949-A
Country	US
Kind code	B2
Filing date	Feb 13, 2014
Priority date	Aug 31, 2011
Publication date	Jan 9, 2018
Grant date	Jan 9, 2018

Abstract

The invention describes a method for degrading off-odors by employing a special 1-aza-3,7-dioxabicyclo[3.3.0]octane compound. Degradation of off-odors to the point of extinction of the off-odor, on hard and/or soft surfaces, in particular on textiles, and in room air, is made possible.

First claim

What is claimed is:

1. A method for degrading off-odors from amine derivatives and sulfur derivatives by employing a 1-aza-3,7-dioxabicyclo[3.3.0]octane compound of the general formula (I)

wherein
R 1 , R 2 , R 3 , R 4 mutually independently denote residues that, in a compound of the general formula R 1 —C(═O)—R 2 or R 3 —C(═O)—R 4 , yield a fragrance aldehyde having at least six carbon atoms or a fragrance ketone having at least six carbon atom,
R 5 , R 6 , R 7 mutually independently denote H or a hydrocarbon residue that can be acyclic or cyclic, substituted or unsubstituted, branched or unbranched as well as saturated or unsaturated

whereby the off-odor is deactivated.

2. The method according to claim 1 , wherein the fragrance aldehyde is selected from the group consisting of adoxal (2,6,10-trimethyl-9-undecenal), anisaldehyde (4-methoxybenzaldehyde), cymal (3-(4-isopropylphenyl)-2-methylpropanal), ethyl vanillin, florhydral (3-(3-isopropylphenyl)butanal), helional (3-(3,4-methylenedioxyphenyl)-2-methylpropanal), heliotropin, hydroxycitronellal, lauraldehyde, lyral (3- and 4-(4-hydroxy-4-methyl pentyl)-3-cyclohexene-1-carboxaldehyde), methyl nonyl acetaldehyde, lilial (3-(4-tert-butylphenyl)-2-methylpropanal), phenyl acetaldehyde, undecylenealdehyde, vanillin, 2,6,10-trimethyl-9-undecenal, 3-dodecen-1-al, alpha-n-amylcinnamaldehyde, melonal (2,6-dimethyl-5-heptenal), 2,4-dimethyl-3-cyclohexene-1-carboxaldehyde (triplal), 4-methoxybenzaldehyde, benzaldehyde, 3-(4-tert-butylphenyl)propanal, 2-methyl-3-(para-methoxyphenyl)propanal, 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-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, 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-dimethylhydrocinnamaldehyde, alpha-methyl-3,4-(methylenedioxy)hydrocinnamaldehyde, 3,4-methylenedioxybenzaldehyde, alpha-n-hexylcinnamaldehyde, m-cymene-7-carboxaldehyde, alpha-methyl phenyl acetaldehyde, 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-methyl pentyl)-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-methyl phenyl acetaldehyde, 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-decadienal, peony aldehyde (6,10-dimethyl-3-oxa-5,9-undecadien-1-al), hexahydro-4,7-methane indane-1-carboxaldehyde, 2-methyloctanal, alpha-methyl-4-(1-methyl ethyl)benzeneacetaldehyde, 6,6-dimethyl-2-norpinene-2-propionaldehyde, para-methyl phenoxy acetaldehyde, 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, methyl nonyl acetaldehyde, hexanal, and trans-2-hexenal.

3. The method according to claim 1 , wherein the fragrance ketone is selected from the group consisting of methyl beta-naphthyl ketone, musk indanone (1,2,3,5,6,7-hexahydro-1,1,2,3,3-pentamethyl-4H-inden-4-one), tonalide (6-acetyl-1,1,2,4,4,7-hexamethyltetraline), alpha-damascone, beta-damascone, delta-damascone, isodamascone, damascenone, methyl dihydrojasmonate, menthone, carvone, camphor, koavone (3,4,5,6,6-pentamethylhept-3-en-2-one), fenchone, alpha-ionone, beta-ionone, gamma-methyl ionone, fleuramone (2-heptylcyclopentanone), dihydrojasmone, cis-jasmon, iso-E-super (1-(1,2,3,4,5,6,7,8-octahydro-2,3,8,8-tetramethyl-2-naphthalenyl)-ethan-1-one (and isomers)), methyl cedrenyl ketone, acetophenone, methyl acetophenone, para-methoxyacetophenone, methyl beta-naphthyl ketone, benzylacetone, benzophenone, para-hydroxyphenyl butanone, celery ketone (3-methyl-5-propyl-2-cyclohexenone), 6-isopropyldecahydro-2-naphthone, dimethyl octenone, Frescomenthe (2-butan-2-yl-cyclohexan-1-one), 4-(1-ethoxyvinyl)-3,3,5,5-tetramethylcyclohexanone, methyl heptenone, 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 (4-(1,3-benzodioxol-5-yl)butan-2-one), hexalone (1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-1,6-heptadien-3-one), isocyclemone E (2-acetonaphthone-1,2,3,4,5,6,7,8-octahydro-2,3,8,8-tetramethyl), methyl nonyl ketone, methyl cyclocitrone, methyl lavender ketone, orivone (4-tert-amyl cyclohexanone), 4-tert-butyl cyclohexanone, delphone (2-pentylcyclopentanone), muscone (CAS 541-91-3), neobutenone (1-(5,5-dimethyl-1-cyclohexenyl)pent-4-en-1-one), plicatone (CAS 41724-19-0), veloutone (2,2,5-trimethyl-5-pentylcyclopentan-1-one), 2,4,4,7-tetramethyloct-6-en-3-one, and tetrameran (6,10-dimethylundecen-2-one).

4. The method according to claim 1 , wherein in the 1-aza-3,7-dioxabicyclo[3.3.0]octane compound of the general formula (I), the residues R 5 and IC mutually independently each denote hydrogen or a C 1-6 hydrocarbon residue that can optionally be substituted.

5. The method according to claim 1 , wherein in the 1-aza-3,7-dioxabicyclo[3.3.0]octane compound of the general formula (I), the residue R 6 denotes a methyl, ethyl, or hydroxymethyl residue, or hydrogen.

6. The method according to claim 1 , wherein in the 1-aza-3,7-dioxabicyclo[3.3.0]octane compound of the general formula (I), the residues R 2 and R 4 each denote hydrogen.

7. The method according to claim 1 , wherein in the 1-aza-3,7-dioxabicyclo[3.3.0]octane compound of the general formula (I), the residues R 2 , R 4 , R 5 , IC each denote hydrogen and the residue R 6 denotes a methyl, ethyl, or hydroxymethyl residue or hydrogen; and that the residues R 1 and R 3 mutually independently each denote a C 6-24 hydrocarbon residue.

8. The method according to claim 1 , wherein the off-odors are present on hard and/or soft surfaces.

9. The method according to claim 1 for degrading off-odors on textiles, in the context of a textile treatment method in which the textile is exposed, in a manual or mechanical washing or soaking process, to a washing bath that contains a 1-aza-3,7-dioxabicyclo[3.3.0]octane compound of the general formula (I), where the temperature of the washing bath is 5 to 95° C.

10. The method according to claim 1 for degrading off-odors on textiles, in which method a liquid containing a 1-aza-3,7-dioxabicyclo[3.3.0]octane compound of the general formula (I) is sprayed onto the textile.

11. The method according to claim 1 for degrading off-odors on hard surfaces, in which method the hard surface is brought into contact with a liquid containing a 1-

Assignees

• Henkel Ag & Co Kgaa

Inventors

• Huchel Ursula
• Weyhe Marc
• Baron Lukas

Classifications

• A61L2103/50

  Textiles, e.g. bedwear or towels · CPC title

• C07D498/08 Primary

  Bridged systems · CPC title

• C11D3/0068

  Deodorant compositions · CPC title

• C11D3/507

  Compounds releasing perfumes by thermal or chemical activation · CPC title

• A61L9/14

  using sprayed or atomised substances {including air-liquid contact processes} · CPC title