WO2008020058A2

WO2008020058A2 - Use of monosaccharides or disaccharides for masking odours and method and composition for masking odours

Info

Publication number: WO2008020058A2
Application number: PCT/EP2007/058529
Authority: WO
Inventors: Martin Bertau; Thomas Henle; Michael Katzberg; Katja Schulz; Gerhard Jörg; Marletta Grosse
Original assignee: Technische Universität Dresden
Priority date: 2006-08-17
Filing date: 2007-08-16
Publication date: 2008-02-21
Also published as: WO2008020058A3; DE102006040276A1

Abstract

The invention relates to the use of at least one monosaccharide and/or at least one disaccharide for masking odours and to compositions for masking odours, containing at least one monosaccharide and/or disaccharide and, optionally, auxiliary agents and additives. The invention also relates to a method for reducing odours in which an object or a surface from which the odour seeps is treated with an active amount of the claimed composition. The invention masks, amongst other things, odours which are produced by substances with an intense smell or substances having a low olfactory threshold, for example, vanillin, garlic, onion and also tobacco smoke. The claimed odour-masking agents can be used in many areas, for example, for masking odours in detergents, conditioners or cleaning agents, cosmetics, medicaments or for air purification.

Description

Use of mono- or disaccharides to mask odors, and methods and composition for masking odors

The invention relates to the use of mono- or disaccharides to mask odors, and to a method and composition for masking odors.

The odor masking agents according to the invention can be used in many areas, for example for the neutralization of perceived as unpleasant odors such. As tobacco smoke, cooking and frying odors or body and animal odors.

Means and methods for masking odors are already known from the prior art.

In this case, a smell is replaced by a more intense odor, e.g. drowned out by using a fragrance. A disadvantage of this method is that one odor load is replaced by another. The cause is not eliminated.

Furthermore, it is known, the odoriferous substance by the use of so-called. Odor absorbers, e.g. based on zeolite or activated carbon. A disadvantage of this method is that in particular activated carbon, but also zeolites are not suitable to mask the perceived as unpleasant odors by applying to living or wearing textiles.

For odor masking also cyclodextrins or cyclodextrin derivatives are also used. Cyclodextrins are toroidally shaped cyclic oligosaccharides consisting of α-1, 4-glycosidically linked glucose molecules. According to the number of glucose molecules, a distinction is made between α-cyclodextrin (composed of six glucose molecules), β-cyclodextrin (composed of seven glucose molecules), γ-cyclodextrin (eight glucose molecules) and δ-cyclodextrin (nine glucose molecules). Cyclodextrins have a hydrophobic central cavity in which lipophilic compounds can be included.

Cyclodextrin-based air improvers or textile binders bind the compounds responsible for the unpleasant odors in the central cavities of the cyclodextrin (FIG. 1). This will mask the odor of the entrapped substances.

Covalently bonded with textile fibers cyclodextrin derivatives are used for the production of "intelligent textiles", which are supposed to bind body odors. A particular disadvantage of the use of cyclodextrins or cyclodextrin derivatives is the fact that cyclodextrins are relatively expensive to prepare and the inclusion of the target substances can be kinetically inhibited because the lipophilic particles causing the unpleasant odor first penetrate the hydrophilic barrier water must before it can be complexed by cyclodextrins.

In addition, α-cyclodextrin is classified as an irritant substance, especially as an eye irritant.

The object of the invention is therefore to provide methods and means for odor masking, which are cheaper to produce than known from the prior art means and even allow a substance inclusion even if it is kinetically inhibited in cyclodextrins. In addition, the substances used should not be toxic or irritating.

According to the invention the object is achieved by the use of at least one mono- and / or a disaccharide for masking odors.

Surprisingly, mono- or disaccharides are able to mask odors. By means of gas chromatographic investigations, the inventors could e.g. prove that the vanilla smell can be retained by the use of mono- or disaccharides.

As shown in Figure 2, mono- and disaccharides adopt a structure which divides them into a hydrophilic and a hydrophobic domain. By hydrophobic interactions with the lipophilic agent, e.g. an odoriferous substance such as vanillin, at the hydrophobic interface, this structure is stabilized. With the addition of a second saccharide unit, this process repeats, which at this stage benefits from the presence of a saccharide, since hydrophilic interactions between the sugars (hydrogen bonds) facilitate co-deposition. By adding more sugar molecules, the growing complex is completed. The advantage is that due to the hydrophobic interactions, the lipophilic particle is directly trapped by the hydrophobic interface, whereas in the case of cyclodextrins (see Figure 1) it would first have to carry out the kinetically unfavorable transfer into the hydrophilic phase.

Advantageously, the mono- and disaccharides of the invention form dynamic complexes with the odor-causing substances, so that a substance inclusion is also possible if it is kinetically inhibited in cyclodextrins. In addition, the mono- and disaccharides of the invention are cheaper than cyclodextrins.

In contrast to α-cyclodextrin, which is classified as an irritant substance and in particular is considered eye irritant, mono- and disaccharides such as glucose and maltose are not toxic. They are not labeled with a danger symbol and in particular have no skin-irritating properties. Mono- and disaccharides are therefore a toxicologically harmless complexing agent for lipophilic agents that produce odors.

In addition, mono- and disaccharides such as glucose and maltose are more soluble in water than cyclodextrins, especially as α-cyclodextrin. This is particularly advantageous when residues of the odor masking agent of the invention and the odoriferous substances entrapped therein are easily removed, e.g. should be eliminated by washing.

With the invention u.a. Masking odors caused by intense odor or low odor threshold substances, e.g. Vanillin, garlic, onion odor, cabbage or fishy odor, cooking and frying odors, waste, body and animal odors, sweat smell, odors due to faeces and urine and "tobacco smoke".

Bad odors are also caused by certain ingredients in detergents such as detergents, fabric softeners or personal care products such as soaps and cosmetics, but also in pharmaceuticals such as plant extracts or pharmaceuticals. These odors can also be masked by the use according to the invention of mono- or disaccharides. When using the mono- or disaccharides according to the invention, the compounds which cause the unpleasant odors are complexed. Advantageously, the detergents and personal care products are not impaired in their effectiveness by the inventive use of mono- or disaccharides for odor masking. The addition of perfumes, which are often triggers of allergies or can cause skin irritation (H. Marquardt, S. Schäfer, Textbook of Toxicology, 2nd ed., Scientific Publishing Company, Stuttgart, 2004, p. 971), to the Übertönung the bad odors By certain ingredients in cleaning products and personal care products can thereby advantageously reduce and ideally completely avoided.

Another advantage of the use according to the invention of mono- or disaccharides for odor masking is the possibility that microorganisms may form the complex-forming additive. use cker as a carbon source. In the course of microbial degradation, the trapped compounds are mitverstoffwechsel, whereby these are permanently eliminated.

This process is especially useful in cosmetic applications: perspiration on the skin is virtually odorless even in poorly ventilated areas of the body. Unpleasant odors are primarily due to microbial metabolic activity.

Microorganisms find in populated areas of the body, which are characterized by a constant moist warm microclimate, by the mono- and disaccharides invention better growth conditions. As a result, microbial metabolic processes are changed and the odor images included according to the invention are eliminated more rapidly microbially.

Another benefit also associated with microbial metabolic activity is the ability of microorganisms to metabolize whiteners and optical brighteners from the fiber. With cotton fabrics, this means that the armpit parts that are frequently affected in this regard assume a yellowish to brownish color. By providing sufficient metabolic energy in the form of the monosaccharides and disaccharides according to the invention, the microorganisms are prevented from degrading the optical brighteners and, at the same time, unpleasant odors are first complexed and later metabolically eliminated.

In a preferred embodiment of the invention, the monosaccharide is selected from the group consisting of trioses, tetroses, pentoses, hexoses or heptoses or derivatives thereof. Particularly preferred is an embodiment in which the monosaccharide is selected from the group consisting of glyceraldehyde, dihydroxyacetone, erythrose, threose, erythrulose, arabinose, lyxose, ribose, deoxyribose, xylose, ribulose, xylulose, allose, galactose, glucose, mannose and fructose , The use of glucose has proved to be particularly suitable.

The disaccharide is selected in a preferred embodiment of the invention from the group consisting of reducing and non-reducing disaccharides or their derivatives. Particularly preferred is an embodiment in which the disaccharide is selected from the group consisting of trehalose, maltose, sucrose or lactose. Particularly suitable is the use of sucrose and / or maltose has been found. The mono- and disaccharides are used singly or in combination.

Preferably, the concentration of the mono- or disaccharides (s) is substantially between 1 and 30 weight percent based on the total composition, preferably between 5 and 20 weight percent, more preferably between 7.5 and 15 weight percent.

The mono- and / or disaccharides for masking odors are preferably used in detergents, care or cleaning agents, cosmetics or medicaments or for air purification.

Part of the invention is the use of mono- or disaccharides for masking odors in the air purification. By air purification (air scrubber) are advantageously higher extraction rates from the exhaust air, for. from production plants to water. In addition, microbial consortia are not polluted, whereby the washing waters are degradable in sewage treatment plants without negative impact on the biological stage.

The invention also includes a composition for masking odors which contains at least one mono- and / or one disaccharide and optionally auxiliaries and additives.

Preferably, the concentration of the mono- or disaccharides (s) in the composition is substantially between 1 and 30 percent by weight based on the total composition, preferably between 5 and 20 percent by weight, more preferably between 7.5 and 15 percent by weight.

In a preferred embodiment of the odor masking composition, the monosaccharide is selected from the group consisting of trioses, tetroses, pentoses, hexoses or heptoses or their derivatives. Particularly preferred is an odor masking composition in which the monosaccharide is selected from the group consisting of glyceraldehyde, dihydroxyacetone, erythrose, threose, erythrulose, arabinose, lyxose, ribose, deoxyribose, xylose, ribulose, xylulose, allose, galacto - se, glucose, mannose and fructose. The use of glulis in a composition for masking odors has proven particularly suitable. The disaccharide is selected in a preferred embodiment of the odor masking composition from the group consisting of reducing and non-reducing disaccharides or their derivatives. Particularly preferred is a odor masking composition in which the disaccharide is selected from the group consisting of trehalose, maltose, sucrose or lactose. Particularly suitable has been the use of sucrose and / or maltose in a composition for masking odors.

The mono- and disaccharides are used individually or in combination in the composition according to the invention.

The composition of the present invention is preferably in a sprayable form so that odors can be easily masked by, for example, spraying the article causing the odor. For example, textiles such as cotton, wool or hides can be treated with the agent according to the invention.

The composition according to the invention for masking odors is preferably present as an aqueous solution.

The composition of the invention is preferably used in detergents, care or cleaning agents, cosmetics or pharmaceuticals or for air purification.

Also part of the invention are washing, care or cleaning agents, cosmetics or medicaments which contain a composition according to the invention for masking odors.

Also part of the invention is a method for reducing odors, wherein an article or a surface from which emanates a smell, is treated with an effective amount of the composition according to the invention.

In a preferred embodiment of the method, the article or surface from which the odor emanates is sprayed with an effective amount of the composition of the invention. Based on the following figures and embodiments, the invention will be explained in more detail without limiting it.

Show

Fig. 1 complexation of the odor molecule vanillin by cyclodextrin

Fig. 2 Complexation of the odor molecule vanillin by maltose (left) and glucosis (right). Deposited in gray are the hydrogen bonds between the glucose units. In contrast, the glucose molecules are glycosidically linked in cyclodextrins.

Fig. 3 Influence of sucrose on the discharge of naphthalene from an aqueous

Solution by a stream of nitrogen. The drawn lines are trend lines.

Embodiment 1

Suppression of the smell of vanillin

A large sheet of cellulose filter paper (diameter 20 cm) was divided into four equal parts. The individual parts were processed differently.

Part 1 (for blank value determination):

The first quarter of the filter paper was sprayed with 1 ml of deionized H ₂ O and completely dried at room temperature. Subsequently, the filter paper was divided into two equal parts. Both parts (eighth) were cut into small pieces and tested with 3 ml of water headspace gas chromatography at a sample temperature of 70 ⁰ C.

As expected, no vanillin could be detected.

Part 2 (for blank value determination):

The second quarter of the filter paper was sprayed with 1 ml of aqueous sugar solution (10% by weight) and completely dried at room temperature. Subsequently, the filter paper was divided into two equal parts. Both parts (eighths) were chopped and examined with 3 ml of water headspace gas chromatography at a sample temperature of 70 ⁰ C. Again, as expected, no vanillin could be detected.

Part 3 (Retention effect of vanillin by sugar):

The third quarter of the filter paper was sprayed with 1 ml of aqueous solution [10% by weight of sugar and saturated with vanillin (5 mg / ml)] and completely dried at room temperature. Subsequently, the filter paper was divided into two equal parts. Both parts (eighth) were cut into small pieces and tested with 3 ml of water headspace gas chromatography at a sample temperature of 70 ⁰ C.

Here vanillin was detected.

Part 4 (Vanilla detection without retention effect):

The fourth quarter of the filter paper was sprayed with 1 ml of saturated vanillin solution (5 mg / ml) and completely dried at room temperature. Subsequently, the filter paper was divided into two equal parts. Both parts (eighth) were cut into small pieces and tested with 3 ml of water headspace gas chromatography at a sample temperature of 70 ⁰ C.

Here vanillin was detected.

The vanillin peak areas determined by headspace gas chromatography are summarized in Table 1.

The headspace-gas chromatographically determined vanillin peak areas (Table 1) showed that in the filter paper - which was sprayed with aqueous vanillin-sugar solution - the vanillin peak areas determined were significantly smaller than the filter paper treated without sugar. These effects are on the order of about 30% peak area loss and are consistent with repeat measurements.

Table 1: Examination of filter papers

Sample preparation: filter paper cellulose

Add (spray) 1, 0 ml aq. Solutions with / without sugar see below Drying 2 h finely chopped

Add 3 ml H ₂ O to the dried filter paper

See:

2 ml vanillin solution (saturated) + 1 ml H ₂ O (without filter paper) 450,000

Used chemicals:

Sugar: sucrose

Sugar solution: 10% by weight of sugar in water

Vanillin-sugar solution: in saturated aqueous vanillin solution, 10% by weight of sucrose was dissolved

Filter paper: Cellulose was sprayed with 1 ml of the aqueous solutions (see above)

Embodiment 2:

Suppression of the odor of menthol

A menthol solution (1/10 of the saturation concentration) without addition of maltose and with maltose additive (5% by weight and 10% by weight) headspace gas chromatography at different sample temperatures (35 ⁰ C / 50 ⁰ C / 70 ⁰ C. ).

Part 1 (for blank value determination):

For the blank determination 3 ml of distilled H ₂ O without the addition of menthol and maltose were headspace gas chromatography at sample temperatures of 35 ⁰ C, 50 ⁰ C and 70 ⁰ C examined.

As expected, no menthol could be detected. Part 2 (retention effect of menthol by maltose):

The aqueous menthol solution [5 and 10 wt .-% maltose] was examined headspace gas chromatography at sample temperatures of 35 ⁰ C, 50 ⁰ C and 70 ⁰ C.

Here menthol was detected.

Part 3 (Menthol detection without retention effect):

The aqueous solution was menthol without the addition of maltose headspace gas chromatography at sample temperatures of 35 ⁰ C, 50 ⁰ C and 70 ⁰ C examined.

Here menthol was detected.

The menthol peak areas determined by headspace gas chromatography are summarized in Table 2.

The menthol peak areas (Table 2) of the menthol solution with addition of maltose determined by headspace gas chromatography were smaller than without maltose addition. These effects are on the order of about 10% peak area loss (at 10% maltose solution) and about 5% peak area loss (at 5% maltose solution), and are about the same order of magnitude at all temperatures and repeat measurements.

TABLE 2 Examination of mentha solution (1/10 of the saturation concentration)

Sample preparation: Examination of the solution without added maltose

Addition of 5% by weight of maltose to the menthaol solution Addition of 10% by weight of maltose to the menthaol solution

Used chemicals:

Sugar: maltose

Sugar solution: 5 and 10% by weight of maltose in water

Menthol-sugar solution: in 1/10 of the saturated aqueous solution of menthol 5 and 5

10% by weight of maltose dissolved

Embodiment 3

Suppression of the smell of naphthalene

A naphthalene solution (24 mg / l) was without addition of sucrose, and sucrose with additive (10 and 20% by weight) headspace gas chromatography at a sample temperature of 35 ⁰ C examined.

Part 1 (for blank value determination):

For the blank determination 3 ml of distilled H ₂ O without the addition of naphthalene and sucrose were headspace gas chromatography at 35 ⁰ C sample temperature studied.

As expected, no naphthalene could be detected.

Part 2 (Retention effect of naphthalene by sucrose):

The aqueous naphthalene solution [10 and 20 wt .-% sucrose] was examined by headspace gas chromatography at 35 ⁰ C sample temperature.

Here, naphthalene was detected.

Part 3 (Naphthalene detection without retention effect):

The aqueous solution was naphthalene without the addition of sucrose headspace gas chromatography at 35 ⁰ C sample temperature studied.

Here, naphthalene was detected.

The naphthalene peak areas determined by headspace gas chromatography are summarized in Table 3. The headspace-gas chromatographically determined naphthalene peak areas (Table 1) of the naphthalene solution with addition of sucrose were significantly smaller than without sucrose addition. These effects are on the order of about 30% peak area loss (at 10% sucrose solution) and about 60% peak area loss (at 20% sucrose solution) and are consistent with repeat measurements.

Table 3: Examination of naphthalene solution (24 mg / l)

Sample preparation: Examination of the solution without added sucrose

Addition of 10% by weight of sucrose to the naphthalene solution Addition of 20% by weight of sucrose to the naphthalene solution

Material Area Naphthalene

Water 0

Water + sucrose 0

Water + sucrose (10% by weight) + naphthalene 375,000

Δ 41%

Water + naphthalene 860,000

Used chemicals:

Sugar: sucrose

Sugar solution: 10 and 20% by weight of sucrose in water

Naphthalene-sugar solution: to 24 mg / l naphthalene solution were dissolved 10 and 20 wt .-% sucrose

Embodiment 4

Slowing down the release of naphthalene

A naphthalene solution (concentration = 14 mg / L) was transferred without the addition of sucrose and with the addition of sucrose (10 wt .-%) in identical gas washing bottles and a constant stream of nitrogen passed through the solutions. At intervals of 15 minutes, the naphthalene fraction still in solution is determined by means of UV / VIS spectroscopy at 275 nm. FIG. 3 shows the influence of sucrose on the discharge of naphthalene from an aqueous solution through a stream of nitrogen. The drawn lines are trend lines. The discharge of naphthalene from an aqueous solution is slowed down in the presence of 10% by weight of sucrose. After 5 hours, the naphthalene content is 53% higher in solutions containing 10% by weight of sucrose.

Used chemicals:

Sugar: sucrose

Sugar solution: 10% by weight of sucrose in water

Naphthalene-sugar solution: to 14 mg / L naphthalene solution was dissolved 10% by weight of sucrose

Claims

claims

1. Use of at least one mono- and / or at least one disaccharide for masking odors.

2. Use according to claim 1, characterized in that the monosaccharide is selected from the group consisting of trioses, tetroses, pentoses, hexoses or heptoses and their derivatives.

3. Use according to claim 2, characterized in that the monosaccharide is selected from the group consisting of glyceraldehyde, dihydroxyacetone, erythrose, threose, erythrulose, arabinose, lyxose, ribose, deoxyribose, xylose, ribulose, xylulose, allose, galactose, glucose, Mannose and fructose.

4. Use according to claim 1, characterized in that the disaccharide is selected from the group consisting of reducing and non-reducing disaccharides and their derivatives.

5. Use according to claim 4, characterized in that the disaccharide is selected from the group consisting of trehalose, maltose, sucrose and lactose.

6. Use according to one of claims 1 to 5, characterized in that the / the mono- or disaccharide (s) is used for masking odors in detergents, care or cleaning agents, cosmetics or pharmaceuticals or for air purification / are.

7. A composition for masking odors, at least containing a mono- and / or disaccharide and optionally auxiliaries and additives.

Composition according to Claim 7, characterized in that the concentration of the mono- or disaccharides (s) is substantially between 1 and 30% by weight relative to the total composition.

Composition according to Claim 8, characterized in that the concentration of the mono- or disaccharides (s) is substantially between 5 and 20% by weight.

Composition according to Claim 9, characterized in that the concentration of the mono- or disaccharides (s) is substantially between 7.5 and 15% by weight.

1 1. A composition according to claim 7, characterized in that the monosaccharide is selected from the group consisting of trioses, tetroses, pentoses, hexoses or heptoses and their derivatives.

12. The composition of claim 1 1, characterized in that the monosaccharide is selected from the group consisting of glyceraldehyde, dihydroxyacetone, erythrose, threose, erythrulose, arabinose, lyxose, ribose, deoxyribose, xylose, ribulose, xylulose, allose, galactose, glucose , Mannose and fructose.

13. The composition according to claim 7, characterized in that the disaccharide is selected from the group consisting of reducing and non-reducing disaccharides and their derivatives.

14. The composition of claim 1 1, characterized in that the disaccharide is selected from the group consisting of trehalose, maltose, sucrose and lactose.

Composition according to any one of Claims 7 to 14, characterized in that the composition is in sprayable form.

A method for reducing odors wherein an article or a surface from which an odor emanates is treated with an effective amount of a composition according to any one of claims 7 to 15.

A method for reducing odors according to claim 16, characterized in that the article or surface from which the odor emanates is sprayed with an effective amount of a composition according to claim 15.

8. washing, care or cleaning agents, cosmetics or medicaments comprising a composition for masking odors according to one of claims 7 to 15.