USE OF CERTAIN COMPOUNDS TO MODIFY, REDUCE, OR ELIMINATE OFF-NOTES

Abstract

The present invention primarily concerns the use of one or more compound(s) with the Formula (I)

X.sub.kY.sub.lZ.sub.mO.sub.n (I),

as described herein, to modify, reduce or eliminate one or more off-note(s) of one or more substance(s) selected from the group (G1) as described herein, through chemical conversion of the substance or rather the substances of the group (G1) and thereupon modifying, reducing or eliminating the off-note(s), in a composition (Z1), which next to one or more compounds of the Formula (I) and the substance or rather the substances of the group (G1) further contains one or more substances selected from the group (G2) as described herein. Furthermore, the present invention concerns new methods for modifying, reducing or eliminating one or more off-note(s) and new compositions obtained therefrom.

Claims

1-14. (canceled)

15. A method for modifying, reducing, or eliminating one or more off-notes of one or more substances of (G1), the method comprising combining one or more compounds of Formula (I) with one or more substances of (G1) in a composition (Z1): the compounds of Formula (I) represented by:
X.sub.kY.sub.lZ.sub.mO.sub.n (I) wherein X=N, Na, K, Mg or Ca, k=0, 1 or 2, Y=C or S, 1=0, 1, 2 or 3, Z=H, with m=0, 1, 2, 3, 4, 5, 6, 7 or 8, and n=2, 3, 4, 5, 6, 7 or 8; and the composition (Z1) comprises: one or more compounds of Formula (I), (G1) one or more substances selected from aldehydes, ketones, unsaturated hydrocarbons, and amines, and (G2) one or more substances selected from alcohols, carboxylic acids, esters, carboxylates, mineral salts, saturated hydrocarbons, silicones, quaternary ammonium compounds, sulfates, and sulphuric acid esters.

16. The method of claim 15, wherein composition (Z1) comprises 0.001 to 30 wt. % of the one or more compounds of Formula (I), based on the total weight of composition (Z1).

17. The method of claim 15, wherein composition (Z1) comprises up to 0.1 wt. % of the one or more substances of (G1), based on the total weight of composition (Z1).

18. The method of claim 15, wherein the mass ratio of the total amount of compounds of Formula (I) to the total amount of substances of group (G1) in composition (Z1) 300:1 to 1:3.

19. The method of claim 15, wherein the molecular weight of the one or more compounds of Formula (I) is 500 g/mol to 30 g/mol.

20. The method of claim 15, wherein the one or more off-notes are selected from roasted, nutty, spicy, bitter, stinging, biting, scratchy, medicinal, fishy, aminous, hay-like, chemical, technical, burnt, fatty, sour, herbaceous, musty, rotten, fermented, terpenous, aromatic, fruity, woody, fleshy, ethereal, earthy, green, solvent-like, rubbery, charred, faecal, urinary, earthy, mushroomy, smoky, decaying, rancid, gasoline-like, buttery, vegetable-like, cooked, animalistic, sweaty, cheesy, cabbage-like, hot, cooling, creamy, flowery, ointment-like, mossy, metallic, workshop-like, indoor swimming pool-like, pyridine-like, pyrazine-like, ensilage-like, carrot-like, adhesive-like, disinfectant-like, dusty, spicy, powdery, astringent, papery, dusty, dry, and floury off-notes.

21. The method of claim 15, wherein the one or more substances of (G1) are selected from the substances of (G1): (G1) linear, branched, cyclic or aromatic aldehydes; linear, branched, cyclic or aromatic ketones; and branched or cyclic amines

22. The method of claim 15, wherein the one or more substances of G2) are selected from the substances of (G2): (G2) compounds with a molecular mass in the range of 18 through 2000 g/mol.

23. The method of claim 15, wherein composition (Z1) further comprises: (G3) one more substances selected from water, methanol, ethanol, propanol, iso-propanol, butanol, pentanol, iso-amylalcohol, hexanol, heptanol, octanol, decanol, dodecanol, hexadecanol, octadecanol, propandiol, butandiol, pentandiol, hexandiol, heptandiol, octandiol, decandiol, dodecandiol, glycerol, sorbitol, propylene glycol, dipropylene glycol, triethyl citrate, methylcellulose, panthenol, iso-amylalcohol, methylbutanol, glucose, starch, formic acid, acetic acid, propionic acid, butyric acid, valeric acid, iso-valeric acid, caproic acid, caprylic acid, pelargonic acid, capric acid, myristic acid, stearic acid, lauric acid, palmitic acid, lactic acid, citric acid, oxalic acid, Na/K formate, Na/K acetate, Na/K propionate, Na/K butyrate, Na/K capronate, Na/K caprylate, Na/K decanoate, Na/K myristate, Na/K laurate, Na/K/Mg/Al/Zn stearate, Na/K palmitate, phytanoic acid, iso-propyl myristate, diethyl phthalate, methyl paraben, ethyl paraben, propyl paraben, lauryl sulfate, sorbitan tristearate, sorbitan monolaurate, sorbitan monooleate, sorbitan trioleate, sorbitan monopalmitate, lauryl ether sulfate, myristyle ether sulfate, paraffin, vasiline, propane, butane, iso-butane, pentane, methybutane, hexane, heptane, octane, nonane, decane, docane, tridecane, undecane, tetradecane, pentadecane, hexadecane, heptadecane, octadecane, menthan, cyclohexane, phytane, squalane, sterane, guaian, cedran, disodium dihydrogen diphosphate, tetra sodium diphosphate, dimethicone, cetylpyridinium chloride, polyquaternium, benzalkonium chloride, cetyltrimethylammonium bromide, benzalkonium chloride and hydrolysed keratin.

24. A method for modifying, reducing or eliminating one or more off-notes comprising: (i) providing a composition (Z0) comprising: one or more substances with off-notes; and one or more substances selected from (G2), (G2), and (G2): (G2) alcohols, carboxylic acids, esters, carboxylates, mineral salts, saturated hydrocarbons, silicones, quaternary ammonium compounds, sulfates and sulphuric acid esters; (G2) compounds with a molecular mass in the range from 18 through 2000 g/mol; and (G2) water, methanol, ethanol, propanol, iso-propanol, butanol, pentanol, iso-amylalcohol, hexanol, heptanol, octanol, decanol, dodecanol, hexadecanol, octadecanol, propandiol, butandiol, pentandiol, hexandiol, heptandiol, octandiol, decandiol, dodecandiol, glycerol, sorbitol, propylene glycol, dipropylene glycol, triethyl citrate, methylcellulose, panthenol, iso-amylalcohol, methylbutanol, glucose, starch, formic acid, acetic acid, propionic acid, butyric acid, valeric acid, iso-valeric acid, caproic acid, caprylic acid, pelargonic acid, capric acid, myristic acid, stearic acid, lauric acid, palmitic acid, lactic acid, citric acid, oxalic acid, Na/K formate, Na/K acetate, Na/K propionate, Na/K butyrate, Na/K capronate, Na/K caprylate, Na/K decanoate, Na/K myristate, Na/K laurate, Na/K/Mg/Al/Zn stearate, Na/K palmitate, phytanoic acid, iso-propyl myristate, diethyl phthalate, methyl paraben, ethyl paraben, propyl paraben, lauryl sulfate, sorbitan tristearate, sorbitan monolaurate, sorbitan monooleate, sorbitan trioleate, sorbitan monopalmitate, lauryl ether sulfate, myristyle ether sulfate, paraffin, vasiline, propane, butane, iso-butane, pentane, methybutane, hexane, heptane, octane, nonane, decane, docane, tridecane, undecane, tetradecane, pentadecane, hexadecane, heptadecane, octadecane, menthan, cyclohexane, phytane, squalane, sterane, guaian, cedran, disodium dihydrogen diphosphate, tetra sodium diphosphate, dimethicone, cetylpyridinium chloride, polyquaternium, benzalkonium chloride, cetyltrimethylammonium bromide, benzalkonium chloride and hydrolysed keratin; (ii) providing one or more compounds of the Formula (I),
X.sub.kY.sub.lZ.sub.mO.sub.n (I), wherein X=N, Na, K, Mg or Ca, k=0, 1 or 2, Y=C or S, 1=0, 1,2 or 3, Z=H, m=0, 1, 2, 3, 4, 5, 6, 7 or 8, and n=2, 3, 4, 5, 6, 7 or 8, (iii) adding the one or more compounds of Formula (I) to composition (Z0) to obtain a composition (Z1), (iv) thermally treating composition (Z1) for 0.1 hours through 168 days at a temperature of 15 to 120 C. and chemically converting the one or more substance selected from (G2), (G2), and (G2) to modify, reduce, or eliminate the undesirable off-notes via the compounds of the Formula (I), so that a composition (Z2) is obtained such that in comparison with the compositions (Z0) and (Z1) the undesirable off-notes are modified, reduced, or eliminated.

25. The method of claim 24, further comprising: (v) adding hydroxide ions to composition (Z2) after the thermal treatment and thermally treating the composition obtained therefrom for 0.1 through 48 hours.

26. The method of claim 24, further comprising irradiating composition (Z1) with UV-light for 0.5 to 96 hours.

27. The method of claim 24, further comprising adding iron and/or copper ions to composition (Z2).

28. A composition (Z2) producible by the method of claim 24, wherein composition (Z2) comprises up to 0.05 wt. % of the one or more compound of Formula (I), based on the total weight of composition (Z2).

29. The method of claim 15, wherein the composition (Z1) comprises 0.01 through 20 wt. % of the one or more compounds of Formula (I), based on the total weight of composition (Z1).

30. The method of claim 15, wherein the composition (Z1) comprises up to 0.001 wt. % of the one or more substances of (G1), based on the total weight of composition (Z1).

31. The method of claim 15, wherein the mass ratio of the total amount of compounds of Formula (I) to the total amount of substances of group (G1) in composition (Z1) from 10:1 through 1:1.

32. The method of claim 15, wherein the molecular weight of the one or more compounds of Formula (I) is 160 g/mol to 30 g/mol.

33. The method of claim 15, wherein the one or more substances of (G1) are selected from the substances of (G1): (G1) compounds with a molecular mass of 18 to 700 g/mol.

34. The method of claim 15, wherein the one or more substances of (G1) are selected from the substances of (G1): (G1) formaldehyde, acetaldehyde, propanal, butanal, pentanal, hexanal, heptanal, octanal, nonanal, decanal, undecanal, dodecanal, tetradecanal, hexadecanal, octadecanal, decadienal, dodecandienal, heptadienal, hexadienal, octadienal, undecandienal, decenal, undecenal, heptenal, trienale and further, octenone, octenal, nonenal, decenal, propanone, butanone, pentanone, pentenone, octadienone, methylnonadienone, pentylfuran, hexanone, heptanone, decanone, methylheptenone, methylheptadienone, methylpropanal, methylbutanal, phenylethanal, hydroxymethylfuranone, hydroxydimethylfuranone, hydroxyethylfuranone, acrolein, benzaldehyde, furfural, furylidenketone, carene, indene, squalene, ocimene, limonene, terpinene, phellandrene, pinene, myrcene, tridecene, tetradecene, dodecene, pentadecene, undecene, decene, nonene, octadecene, heptadecene, hexadecene, farnesene, humulene, butene, pentene, methylpentene, butandiene, methylbutadiene, undectriene, longifolen, menthadiene, methylbutene, styrene, methylamine, dimethylamine, trimethylamine, ethylamine, diethylamine, triethylamine, butylamine, ethanolamine, diethanolamine, triethanolamine and furfurylamine.

Description

EXAMPLE 1BODY GEL

[0069] Upon application of a body gel on the skin or rather upon applying crme, after a certain time, also a certain undesirable off-note was perceived next to the perfuming, which was described as technical, fishy, musty. The analysis of the formulation via different methods resulted in that the used polyquat (quaternary amino compounds), which releases trimethylamine, was the reason for this undesirable off-note.

Production of the Body Gel:

[0070]

TABLE-US-00001 Mix A Mix B Mix C Mix D Mix E Phase Ingredients INCI [wt.-%] [wt.-%] [wt.-%] [wt.-%] [wt.-%] A Water Water (Aqua) 84.50 84.45 84.45 96.10 96.05 Glycerol Glycerol 2.00 2.00 2.00 2.00 2.00 B Polyquaternium- Polyquaternium- 0.80 0.80 0.8 0.80 0.80 37 37 Percarbamide Urea peroxide 0 0.05 0.05 0 0.05 C Sodiumhydroxide Sodiumhydroxide, 0.50 0.50 0.50 0.50 0.50 solution water 10% D Hydrochloric Hydrochloric 0.60 0.60 0.60 0.60 0.60 acid solution acid, water 10% E Symdiol68 1,2- 0.50 0.50 0.50 0 0 hexandiol, caprylyl glycol Hydrolite 5 Pentylene 5.00 5.00 5.00 0 0 glycol Extrapone Water, 1.00 1.00 1.00 0 0 Hibiscus propylene glycol, glucose, Hibiscus extract Timiron Sun Mica, titanium 0.10 0.10 0.10 0 0 gold Sparkle dioxide, MP-29 iron oxide F Neo-PCL water Trideceth-9, 3.00 3.00 3.00 0 0 Soluble N PEG-5, ethyl hexanoate, water Perfume Perfume 1.00 1.00 0.95 0 0 Propylene Propylene 0 0 0.05 0 0 glycol glycol Solubilizer PEG-40 1.00 1.00 1.00 0 0 Hydrogenated castor oil, tridedeth-9, propylene glycol, water

[0071] Phase A and phase B were mixed and dissolved homogeneously while stirring at 40 C. for 2 hours. After the addition of phase C, is was stirred further for 1 hour at 40 C. After that, phase D was added while stirring and the temperature was lowered to room temperature. After mixing phase E, it was added while stirring. Then, phase F was mixed and added to the batch while stirring.

Application Test:

[0072] 150 mg of each mixture was distributed evenly over a forearm skin area of 73 cm using a spatula. After about 30 seconds, the off-note was perceptible and was examined both sensorially and analytically. Therefore, the perfumed mixtures A, B and C as well as the unperfumed mixtures D and E were compared.

Sensory Examination:

[0073] The sensory examinations were carried out by means of a sensory-trained group of 15 persons, whereby the samples were randomized and coded, whereby both the perceived intensity and the perceived sensory impression itself were described. This group evaluated the intensity of the perceived impressions (total intensity), as well as the perceived intensity of the off-note on a scale from 0 to 9, whereby 0 stands for no perceived intensity and 9 for a highly intense intensity impression. Furthermore, the group described the sensory impressions with different attributes.

[0074] a) Results of the Perfumed Mixtures A, B and C:

TABLE-US-00002 Perfumed mixtures Mix A Mix B Mix C Total intensity 6.3 7.2 6.4 Intensity of the 4.7 1.5 1.4 off-note Description flowery, fruity, fresh, fruity, flowery, fresh, fishy, technical, flowery, musty fruity, musty musty Total intensity in comparison with Increase by 14% comparable Mix A Intensity of the off-note in Reduction by Reduction by comparison with Mix A 68% 70%

[0075] The intensity of the off-note of mixture A was classified as perceptible (4) to clearly perceptible (5), while mixtures B and C were rated as barely perceptible (1) to weakly perceptible (2). Thus, mixtures B and C showed a significant reduction of the off-note intensity compared to mixture A.

[0076] b) Results of the Unperfumed Mixtures D and E:

TABLE-US-00003 Unperfumed mixtures Mix D Mix E Total intensity 5.1 1.5 Intensity of the 5.1 1.5 off-note Description fishy, technical, technical, musty musty Intensity of the off-note in Reduction by comparison with Mix D 71%

[0077] Since these were unperfumed mixtures, only the off-note was perceptible and the overall intensity was identical to the off-note intensity. The intensity of the off-note of mixture D was clearly perceived (5), while the mixture E was rated as barely perceptible (1) to weakly perceptible (2). Thus the mixture E showed a clear reduction of the off-note intensity of 71% compared to mixture D.

[0078] Analytical Examination:

[0079] The trimethylamine, the cause of the undesirable off-note, could only be analysed in the trace range at the detection limit of the GC-MS in the unperfumed mixtures D and E. In the perfumed mixtures A, B and C coelutions of the trimethylamine with other ingredients occurred. The determination of the trimethylamine was carried out in the vapour phase over the mixture applied to the forearm, analogously to the sensory evaluation. This headspace with the trimethylamine was continuously sucked off and the trimethylamine was deposited on the Tenax carrier matrix. The headspace sampling was performed at room temperature and at a flow of 100 mL/min for 15 minutes. This carrier matrix loaded with trimethylamine was sampled by means of a GC/MS and the MS areas (counts) were determined. From the determined areas of mixtures D and E, a factor was determined by proportioning the proportions.

TABLE-US-00004 Unperfumed mixtures Mix D Mix E Areas trimethylamine 82586 7859 Area factor von mixture D and E 10.5

[0080] The area and thus the released amount of trimethylamine has been reduced by a factor of 10.5.

EXAMPLE 2ETHANOL

[0081] Ethanol is used, among others, for producing flavour blends for products in the food, cosmetics (personal care), household (home care), fine fragrance, oral care, pharmaceuticals and pet food sectors. Depending on the production and quality of the ethanol, it may contain undesirable off-notes, which are annoying in the product and reduce its quality. The undesirable off-note was described as greasy, rancid, fermented, cheesy, spicy. The investigations showed that this unwanted off-note was mainly caused by acrolein, butanal, hexanal, butanedione, acetoin and pentanedione.

[0082] Sample Production:

TABLE-US-00005 I II III IV V VI Phase Ingredient [wt.-%] [wt.-%] [wt.-%] [wt.-%] [wt.-%] [wt.-%] A Ethanol 100 0 99.84 94 0 93.84 with off- note B Ethanol 0 100 0 0 94 0 p.A. C Sodium 0 0 0.05 0 0 0.05 percarbonate D Sodium 0 0 0.05 0 0 0.05 hydroxide solution 10% E Hydrochloric 0 0 0.06 0 0 0.06 acid solution 10% F Aroma 0 0 0 6 6 6

[0083] To prepare the samples, the phase C was added to the phase A in a glass vessel and stirred closed for 24 hours at room temperature. Then, the phase D was added and stirred closed for 4 hours at room temperature. While stirring, the addition of the phase E was made, then the addition of the phase F was made.

[0084] Sensory Evaluation:

[0085] The samples were tempered to room temperature in a closed screw-cap glass vessel, wherein the same vessels and sample volumes were used. For each measurement, a maximum of 6 to 10 samples was evaluated, and blank samples with tap water as well as some double identical samples were measured. The sensory evaluation was performed by a sensory-trained group of 15 persons as well as randomized and coded samples, wherein both the perceived intensity and the perceived sensory impression itself were described. This group evaluated the intensity of the perceived impressions (total intensity) as well as the perceived intensity of the off-note on a scale from 0 to 9, wherein 0 stands for no perceived intensity and 9 for a highly intense intensity impression. Furthermore, the sensory impressions were described with different attributes by the group.

TABLE-US-00006 Total Intensity intensity off-note Description Results Blind 0.1 0 neutral, odourless Comparison of the off- I 4.8 4.5 greasy, fermented, cheesy, note intensity of the vegetables, rancid, alcoholic, initial sample I with the spicy treated sample III II 1.5 0.4 alcoholic, neutral, technical, Reduction by 90% medicinal III 1.8 0.5 alcoholic, greasy, spicy Comparison of the off- IV 6.0 4.4 greasy, vegetables, spicy, note intensity of the orange, citrus, fruity, flowery initial sample IV with V 6.3 0 citrus, orange, fresh, fruity, the treated sample VI flowery Reduction by 91% VI 6.1 0.4 citrus, orange, fruity, flowery, spicy

[0086] The treated sample III showed a reduction of the off-note intensity by 90% and tended to be comparable with sample II (ethanol p.A.). The same tendencies were found in the aromatized samples. In the treated aromatized sample VI, the intensity of the off-note was evaluated as barely perceptible and was significantly reduced by 91%.p

[0087] Analytical Examination:

[0088] The unwanted off-note was mainly caused by acrolein, butanal, hexanal, butanedione, acetoin and pentanedione and could only be analyzed in the trace range by GC-MS in the non-aromatized samples I and III. In the aroma containing samples IV and VI, the substances causing the off-notes were masked by the added aroma substances and could therefore not be analyzed. The determination of the individual off-note components was carried out, analogous to the sensory evaluation, in the vapour phase above the sample in the screw cap jars at room temperature. This headspace with the off-note components was continuously sucked off, whereby the off-note components then accumulated on the Tenax carrier matrix. The headspace sampling was performed at room temperature and a flow of 100 mL/min for 30 minutes. The carrier matrix loaded with the off-note components was measured using GC/MS and the MS areas (counts) of the individual compounds causing the off-notes were evaluated. For the determination of the total off-note, the areas and thus the quantities of the individual off-note components were combined to a total area. These total areas of the samples I and III were put into relation and a factor was determined.

TABLE-US-00007 Sample I Sample III Total surface area off-note 5252214 535741 components Area factor of mixture D and E 9.8

[0089] The total surface area of the off-note components and thus the quantity in the headspace has been reduced by a factor of 9.8.