WO2014077640A1

WO2014077640A1 - Composition for slow emission of fragrance comprising complexes of cucurbituril and fragrance molecule

Info

Publication number: WO2014077640A1
Application number: PCT/KR2013/010434
Authority: WO
Inventors: Kimoon Kim; Young Ho Ko; Su Hyun Lee; Selvapalam Narayanan; Don Wook Lee
Original assignee: Postech Academy-Industry Foundation
Priority date: 2012-11-16
Filing date: 2013-11-15
Publication date: 2014-05-22

Abstract

Disclosed herein is a composition for slowly releasing a fragrant molecule, including a complex of cucurbituril and a fragrant molecule. The composition is advantageous in that the fragrant molecule is more slowly released when it exists in the form of a complex compared to when it exists alone. Therefore, when a product including this complex is manufactured, the reduction of a fragrant material due to the long-term storage thereof can be minimized, and a fragrant material can be released for a long period of time compared to conventional products. Accordingly, it is presumed that this composition will be applied to air cleaning and environment improvement.

Description

COMPOSITION FOR SLOW EMISSION OF FRAGRANCE COMPRISING COMPLEXES OF CUCURBITURIL AND FRAGRANCE MOLECULE

The present invention relates to a composition for slowly releasing a fragrant molecule, the composition including a complex of cucurbituril and a fragrant molecule, and a method of preparing the same.

To date, as an air freshener, a fragrant material itself or a polymer structure physically impregnated with a fragrant material has been used. Recently, in order to develop a fragrant material which can maintain a fragrance effect for a long period of time, macrocyclic molecules that can interact with fragrant molecules have attracted considerable attention. Cyclodextrin is a typical example of such macrocyclic molecules. Cyclodextrin was discovered in 1891 and has been actively researched ever since it was found that cyclodextrin reacts with several compounds to form inclusion complexes. Thus, cyclodextrin has been utilized in various fields such as food manufacture, medicine and the like.

Meanwhile, cucurbituril, which is another typical macrocyclic molecule, has attracted considerable attention as an alternative to cyclodextrin in various application fields. Particularly, characteristics of cucurbituril, such as high stability, high selectivity, strong bonding force and the like, were ascertained by scholarly basic research. For this reason, cucurbituril has been researched in various fields, such as molecular structures, chromatography, catalytic reactions, drug delivery, biosensors (biochips), nanodevices, etc.

International Patent Application Publication No. WO 2000/68232 discloses cucurbit[n]uril which is represented by the following Chemical Formula below:

[Chemical Formula]

wherein n is an integer of 4 to 12.

Each of the cucurbituril derivatives is a compound composed of glycoluril monomers having no substituent group (KR-A-10-2007-0073225).

Cucurbituril, which is a macrocyclic compound, has a hydrophobic cavity, and has hydrophilic inlets at both sides thereof. Therefore, hydrophobic interaction occurs in the cavity of cucurbituril, and hydrogen bonding, polar interaction, cation-polar interaction and the like occur at the upper and lower inlets thereof at which six carbonyl groups are located, so cucurbituril exhibits inclusion effects using extremely stable noncovalent binding with various kinds of compounds. Particularly, cucurbituril is formed into a complex by extremely stable noncovalent binding with compounds having a functional group such as an amino group, a carboxylic group or the like. Thanks to it having such characteristics, cucurbituril can be used as a material for slowly releasing a fragrance, based on interaction stronger than that of cyclodextrin.

It is proposed in the prior patent of the present inventors that cucurbituril can be used as a bad odor remover or the like because it has a structure which can be bonded with an organic compound. However, experiments that may support the possibility have never been carried out by the present inventors or other researchers. Thus, the present inventors experimentally found that cucurbituril can slowly release a fragrant molecule when it reacts with a fragrant molecule in its cavity to form a complex, and the present inventors also found the optimal composition ratio of the complex and the optimal conditions required to exhibit functions. Based on these findings, the present invention was completed.

Accordingly, the present invention has been devised to solve the above-mentioned problems, and an object of the present invention is to provide a composition for slowly releasing a fragrant molecule, the composition including a complex of cucurbituril and a fragrant molecule. This composition is characterized in that a fragrant molecule is slowly released.

However, an object to be accomplished by the present invention is not limited to the above-mentioned object, and other objects (not mentioned) will be clearly understood from the following descriptions by those skilled in the art.

In order to accomplish the above object, an aspect of the present invention provides a composition for slowly releasing a fragrant molecule, the composition including a complex of a fragrant molecule and a compound represented by Chemical Formula 1 below:

[Chemical Formula 1]

wherein n is an integer of 4 to 20, and X is O, S or NH, and

wherein the composition includes 45 to 100 wt% of the compound of Chemical Formula 1 of n = 7.

The compound of Chemical Formula 1 is cucurbituril.

As described above, the composition including a complex of cucurbituril and a fragrant molecule according to the present invention is advantageous in that the fragrant molecule is more slowly released when it exists in the form of a complex compared to when it exists alone. Therefore, when a product including this complex is manufactured, the reduction of a fragrant material due to the long-term storage thereof can be minimized, and a fragrant material can be released for a long period of time compared to conventional products. Accordingly, it is presumed that this composition will be applied to air cleaning and environment improvement.

The above and other objects, features and advantages of the present invention will be more clearly understood from the following detailed description taken in conjunction with the accompanying drawings, in which:

FIG. 1 is a schematic view showing a complex of cucurbituril and a fragrant molecule;

FIG. 2 is a view showing the 1H-NMR results of menthol bonded with cucurbit[6]uril, menthol bonded with cucurbit[7]uril and menthol bonded with cucurbit[8]uril;

FIG. 3 is a graph showing the results of measuring the release rates of ethyl butyrate from a complex of cucurbituril and ethyl butyrate in the state of an aqueous solution;

FIG. 4 is a graph showing the results of measuring the release rates of ethyl butyrate from a complex of cucurbituril and ethyl butyrate in the dry state;

FIG. 5 is a graph showing the results of measuring the release rates of camphor from a complex of cucurbituril and camphor in the state of an aqueous solution;

FIG. 6 is a graph showing the results of measuring the release rates of camphor from a complex of cucurbituril and camphor in the dry state;

FIG. 7 is a graph showing the results of measuring the release rates of menthol from a complex of cucurbituril and menthol in the state of an aqueous solution;

FIG. 8 is a graph showing the results of measuring the release rates of menthol from a complex of cucurbituril and menthol in the dry state;

FIG. 9 is a graph showing the results of measuring the release rates of hexanal from a complex of cucurbituril and hexanal in the state of an aqueous solution; and

FIG. 10 is a graph showing the results of measuring the release rates of hexanal from a complex of cucurbituril and hexanal in the dry state.

Hereinafter, preferred embodiments of the present invention will be described in detail with reference to the attached drawings.

The present invention provides a composition for slowly releasing a fragrant molecule, the composition including a complex of a fragrant molecule and a compound represented by Chemical Formula 1 below:

[Chemical Formula 1]

wherein n is an integer of 4 to 20, and X is O, S or NH, and

The compound of Chemical Formula is cucurbituril.

According to the experiment of the present inventors (refer to Example 1), since the cavity of cucurbit[7]uril, which is the compound of Chemical Formula 1 of n = 7, is most easily bonded with a fragrant material, cucurbit[7]uril is most advantageous in terms of slowly releasing a fragrant molecule. In this case, it is preferred that the ratio of the amount of cucurbit[7]uril to the total amount of cucurbituril be high. However, in order to increase the amount of cucurbit[7]uril at the time of synthesizing cucurbit[7]uril, a process of purifying the synthesized cucurbit[7]uril (crude cucurbit[7]uril) is additionally required, thus decreasing economical efficiency. Therefore, the synthesized crude cucurbit[7]uril itself can be used to slowly release a fragrant molecule, and, in this case, the amount of cucurbit[7]uril in the crude cucurbit[7]uril may be 45% to 100% based on the total amount of cucurbituril. The composition may further include cucurbiturils of Chemical Formula 1 of n = 4 to 6 and 8 to 20 in an amount of 0 ~ 35%. Among the cucurbiturils of Chemical Formula 1 of n = 4 to 6 and 8 to 20, cucurbit[6]uril is mostly used. Besides, the composition may further include cucurbiturils of Chemical Formula 1 of n = 4, 5 and 8 to 20 in an amount of 0 ~ 5%.

The crude cucurbit[7]uril is synthesized by a method including the following steps. However, the synthesis method thereof is not limited thereto.

1) Glycoluril 1.05 M (150g) and paraformaldehyde 2.2 M (67g) are mixed with a sufficient amount of HCl (225mL), and this mixture is heated to 85 ~ 90℃ for 18 hours to obtain a cucurbituril solution.

2) H₂O (3L) is added to the cucurbituril solution, and then the solution is filtered to obtain a filtrate, and then the filtrate is mixed with methanol (2.4L) to obtain a solid-containing solution.

3) The solid-containing solution is filtered by a filter paper to obtain a solid compound, and then the solid compound is washed with methanol (2L) and dried to obtain crude cucurbit[7]uril.

According to an embodiment of the present invention, the complex of a compound of Chemical Formula 1 and a fragrant molecule is characterized in that the molar ratio of the compound to the fragrant molecule is 1: 0.5 ~ 1. Preferably, the molar ratio of the compound to the fragrant molecule may be 1: 1. Cucurbituril has a cavity. As the number of fragrant molecules charged in the cavity increases, the bonding rate of cucurbituril and fragrant molecules increases. Therefore, when a large number of fragrant molecules are bonded with cucurbituril, a large number of fragrant molecules are released, but characteristics of the complex are maintained constant regardless of the bonding rate thereof, and the complex is more easily formed when the molar ratio of cucurbituril to the fragrant molecule is 1: 0.5 ~ 1. The composition ratio of the complex is determined according to the solubility of a fragrant material in water and the amount of volatilized fragrant material with respect to temperature.

According to another embodiment of the present invention, the fragrant molecule may be selected from the group consisting of ethyl butyrate, camphor, menthol, hexanal, eugenol, citronellol, linalool, patchoulol, santalol, phenyl ethyl alcohol, terpineol, vanillin, benzaldehyde, methyl salicylate, isoamyl acetate, d-limonene, L-limonene, α-pinene, 2-hydroxy-p-cymene, methyl acetophenone, and cis-jasmone. However, the kinds of the fragrant molecules are not limited thereto.

According to still another embodiment of the present invention, the composition may further include water. According to the experiment of the present inventors, the fragrant molecule releasing function of cucurbituril is maximized when it exists in the state of an aqueous solution compared to when it exists in the dry state.

FIG. 1 is a schematic view showing a complex of cucurbituril and a fragrant molecule.

A method of preparing a complex of cucurbituril and a fragrant molecule includes the steps of: (i) mixing the compound of Chemical Formula 1 with a fragrant mole to obtain a mixture; (ii) adding an aqueous solution to the mixture to obtain a mixed solution; and (iii) volatilizing the mixed solution to form a dry complex for slowly releasing a fragrant molecule.

Hereinafter, the present invention will be described in more detail with reference to the following Examples. However, these Examples are set forth to illustrate the present invention, and the scope of the present invention is not limited thereto.

[Examples]

Example 1: Determining cucurbituril suitable for preparing a fragrant molecule complex

1-1: Determining cucurbituril

There are various cucurbituril derivatives. The present inventors expected that cucurbit[7]uril, among the cucurbituril derivatives, would be most suitable for preparing a fragrant molecule complex. The reason for this is as follows.

First, cucurbit[7]uril can easily capture a fragrant molecule because it has a large cavity. In contrast, cucurbit[5]uril cannot be easily bonded with a fragrant molecule because it has very small cavity, and cucurbit[6]uril cannot be easily bonded with commonly-used fragrant molecule because it has such a cavity that only one linear alkyl chain can get into the cavity. (* Comparison of sizes of cavities of cucurbituril derivatives: cucurbit[8]uril > cucurbit[7]uril > cucurbit[6]uril > cucurbit[5]uril)

Second, cucurbit[7]uril is easily dissolved in water because it has high solubility in water. The solubility of cucurbit[6]uril or cucurbit[8]uril in water is less than 10^-5M because it has a symmetric molecule structure. In contrast, the solubility of cucurbit[7]uril in water is about 2 ~ 3 × 10^-2 M, which is high.

Therefore, the present inventors carried out the following experiment in order to confirm the expected results.

A complex was prepared by mixing 100 mg of cucurbit[7]uril and 11.8 mg of menthol at a molar ratio of 1: 1. 79.5 mg of cucurbit[6]uril and 118.3 mg of cucurbit[8]uril were respectively put into two mortars, and 11.8 mg of menthol was added to each of the mortars. 0.5 mL of distilled water was added to form a slurry, and then the slurry was stirred for 10 minutes using a pestle to prepare a complex. The complex was dried in an oven at 40℃ for 6 hours. The dried complexes were analyzed by 1H-NMR.

The 1H-NMR results thereof are shown in FIG. 2. As shown in FIG. 2, it can be ascertained that cucurbit[6]uril is barely bonded with menthol, cucurbit[8]uril is weakly bonded with menthol, and cucurbit[7]uril is strongly bonded with menthol.

Example 2: Preparation of complex of slowly releasing fragrant molecule, the complex including cucurbituril and ethyl butyrate, and evaluation of release rate of the fragrant molecule

2-1: Evaluation of release rate of fragrant molecule in aqueous solution

100 mg of cucurbit[7]uril and 8.8 mg of ethyl butyrate were put into a mortar. Subsequently, 0.5 mL of distilled water was added to the mortar to form a slurry, and then the slurry was stirred for 10 minutes using a pestle to prepare a complex. The complex was dried in an oven at 40℃ for 6 hours. 7.4 mg of the dried complex was dissolved in 2.5 mL D₂O, and was sonicated until it was completely dissolved, thus obtaining a solution.

Each of four 20 mL glass vials was charged with 0.5 mL of the obtained solution, and was then left at room temperature or 40℃. The residual 0.5 mL solution was immediately measured by 1H-NMR, and each of the solutions charged in the glass vials was measured by 1H-NMR after 0.5 hours, 1.5 hours, 3 hours and 5 hours, thus evaluating the amount of reduction of ethyl butyrate to the passage of time. In this case, air is introduced into each of the vials such that air is sufficiently circulated therein. Since cucurbit[7]uril is hardly volatilized due to its high molecular weight, the amount of reduction of ethyl butyrate was relatively quantitated by the integration ratio of NMR peak of cucurbit[7]uril and NMR peak of ethyl butyrate.

When a fragrant material (ethyl butyrate) existed alone, the amount of reduction of the fragrant material (ethyl butryrate) was evaluated based on methanesulfonic acid under the condition that cucurbit[7]uril does not exist. The results thereof are shown in FIG. 3. As shown in FIG. 3, it can be seen that, when ethyl butyrate existed alone, it took 0.5 hours (red full line) to completely release ethyl butyrate, but when ethyl butyrate was formed into a complex together with cucurbit[7]uril, it took 1.5 hours (blue full line) to completely release ethyl butyrate. From the experimental results, it can be ascertained that, when ethyl butyrate was formed into a complex together with cucurbit[7]uril, the reduction rate of ethyl butyrate became about three times lower compared to when ethyl butyrate existed alone.

2-2: Evaluation of release rate of fragrant molecule in dry state

100 mg of cucurbit[7]uril and 11.5 mg of ethyl butyrate were put into a mortar. Subsequently, 0.5 mL of distilled water was added to the mortar to form a slurry, and then the slurry was stirred for 10 minutes using a pestle to prepare complex samples. The complex samples were dried in an oven at 40℃ for 6 hours. Some of the dried complex samples were immediately measured by 1H-NMR, and others thereof were respectively charged in two 20 mL glass vials, and were then left at room temperature or 40℃. In this case, air is introduced into each of the vials such that air is sufficiently circulated therein. After 4 days, the amount of residual ethyl butyrate was evaluated by 1H-NMR measurement.

The experimental results thereof are shown in FIG. 4. From the experimental results shown in FIG. 4, it can be seen that the amount of ethyl butyrate bonded with cucurbit[7]uril was reduced by about 14% at room temperature for 4 days in the dry state. Further, it can be seen that, even when the experiment was carried out at 40℃ or more, the amount thereof was reduced similarly to such degree. That is, it can be seen that the release of ethyl butyrate from cucurbit[7]uril is very restricted in the dry state regardless of temperature.

Example 3: Preparation of complex of slowly releasing fragrant molecule, the complex including cucurbituril and camphor, and evaluation of release rate of the fragrant molecule

3-1: Evaluation of release rate of fragrant molecule in aqueous solution

100 mg of cucurbit[7]uril and 11.5 mg of camphor were put into a mortar. Subsequently, 0.5 mL of distilled water was added to the mortar to form a slurry, and then the slurry was stirred for 10 minutes using a pestle to prepare a complex. The complex was dried in an oven at 40℃ for 6 hours. 7.4 mg of the dried complex was dissolved in 2.5 mL D₂O, and was sonicated until it was completely dissolved, thus obtaining a solution.

Each of four 20 mL glass vials was charged with 0.5 mL of the obtained solution, and was then left at room temperature. The residual 0.5 mL solution was immediately measured by 1H-NMR, and each of the solutions charged in the glass vials was measured by 1H-NMR after 0.5 hours, 1.5 hours, 3 hours and 5 hours, thus evaluating the amount of reduction of camphor to the passage of time. In this case, since cucurbit[7]uril is hardly volatilized due to its high molecular weight, the amount of reduction of camphor was relatively quantitated by the integration ratio of NMR peak of cucurbit[7]uril and NMR peak of camphor. When a fragrant material (camphor) existed alone, the amount of reduction of the fragrant material (camphor) was evaluated based on methanesulfonic acid under the condition that cucurbit[7]uril does not exist. The results thereof are shown in FIG. 5.

As shown in FIG. 5, it can be seen that, when camphor existed alone, it took 3 hours (red full line) to completely release camphor, but when camphor was formed into a complex together with cucurbit[7]uril, only 10% of camphor was released during 5 hours (blue full line). From the experimental results, it can be ascertained that, when camphor was formed into a complex together with cucurbit[7]uril, the reduction rate of camphor became very low compared to when camphor existed alone.

3-2: Evaluation of release rate of fragrant molecule in dry state

100 mg of cucurbit[7]uril and 11.5 mg of camphor were put into a mortar. Subsequently, 0.5 mL of distilled water was added to the mortar to form a slurry, and then the slurry was stirred for 10 minutes using a pestle to prepare complex samples. The complex samples were dried in an oven at 40℃ for 6 hours. Some of the dried complex samples were immediately measured by 1H-NMR, and others thereof were respectively charged in two 20 mL glass vials, and were then left at room temperature or 40℃. In this case, air is introduced into each of the vials such that air is sufficiently circulated therein. After 3 days, the amount of residual camphor was evaluated by 1H-NMR measurement. The experimental results thereof are shown in FIG. 6.

From the experimental results shown in FIG. 6, it can be seen that the amount of ethyl butyrate bonded with cucurbit[7]uril was hardly changed at room temperature for 3 days in the dry state. Further, it can be seen that, even when the experiment was carried out at 40℃ or more, the amount thereof was not reduced. That is, it can be seen that the release of camphor from cucurbit[7]uril is very restricted in the dry state regardless of temperature.

Example 4: Preparation of complex of slowly releasing fragrant molecule, the complex including cucurbituril and menthol, and evaluation of release rate of the fragrant molecule

4-1: Evaluation of release rate of fragrant molecule in aqueous solution

100 mg of cucurbit[7]uril and 11.8 mg of menthol were put into a mortar. Subsequently, 0.5 mL of distilled water was added to the mortar to form a slurry, and then the slurry was stirred for 10 minutes using a pestle to prepare a complex. The complex was dried in an oven at 40℃ for 6 hours. 7.4 mg of the dried complex was dissolved in 2.5 mL D₂O, and was sonicated until it was completely dissolved, thus obtaining a solution. Each of four 20 mL glass vials was charged with 0.5 mL of the obtained solution, and was then left at room temperature. The residual 0.5 mL solution was immediately measured by 1H-NMR, and each of the solutions charged in the glass vials was measured by 1H-NMR after 0.5 hours, 1.5 hours, 3 hours and 5 hours, thus evaluating the amount of reduction of menthol to the passage of time. In this case, since cucurbit[7]uril is hardly volatilized due to its high molecular weight, the amount of reduction of menthol was relatively quantitated by the integration ratio of NMR peak of cucurbit[7]uril and NMR peak of menthol. When a fragrant material (menthol) existed alone, the amount of reduction of the fragrant material (menthol) was evaluated based on methanesulfonic acid under the condition that cucurbit[7]uril does not exist. The results thereof are shown in FIG. 7.

As shown in FIG. 7, it can be seen that, when menthol existed alone, it took 3 hours (red full line) to completely release menthol, but when menthol was formed into a complex together with cucurbit[7]uril, only 75% of menthol was released during 5 hours (blue full line). From the experimental results, it can be ascertained that, when menthol was formed into a complex together with cucurbit[7]uril, the reduction rate of menthol became very low compared to when menthol existed alone.

4-2: Evaluation of release rate of fragrant molecule in dry state

100 mg of cucurbit[7]uril and 11.8 mg of menthol were put into a mortar. Subsequently, 0.5 mL of distilled water was added to the mortar to form a slurry, and then the slurry was stirred for 10 minutes using a pestle to prepare complex samples. The complex samples were dried in an oven at 40℃ for 6 hours. Some of the dried complex samples were immediately measured by 1H-NMR, and others thereof were respectively charged in two 20 mL glass vials, and were then left at room temperature or 40℃. In this case, air is introduced into each of the vials such that air is sufficiently circulated therein. After 3 days, the amount of residual menthol was evaluated by 1H-NMR measurement. The experimental results thereof are shown in FIG. 8.

From the experimental results shown in FIG. 8, it can be seen that the amount of menthol bonded with cucurbit[7]uril was reduced by about 4% at room temperature for 3 days in the dry state. Further, it can be seen that, even when the experiment was carried out at 40℃ or more, the amount thereof was reduced similarly to such degree. That is, it can be seen that the release of menthol from cucurbit[7]uril is very restricted in the dry state regardless of temperature.

Example 5: Preparation of complex of slowly releasing fragrant molecule, the complex including cucurbituril and hexanal, and evaluation of release rate of the fragrant molecule

5-1: Evaluation of release rate of fragrant molecule in aqueous solution

100 mg of cucurbit[7]uril and 7.6 mg of hexanal were put into a mortar. Subsequently, 0.5 mL of distilled water was added to the mortar to form a slurry, and then the slurry was stirred for 10 minutes using a pestle to prepare a complex. The complex was dried in an oven at 40℃ for 6 hours. 7.1 mg of the dried complex was dissolved in 2.5 mL D₂O, and was sonicated until it was completely dissolved, thus obtaining a solution. Each of four 20 mL glass vials was charged with 0.5 mL of the obtained solution, and was then left at room temperature. The residual 0.5 mL solution was immediately measured by 1H-NMR, and each of the solutions charged in the glass vials was measured by 1H-NMR after 0.5 hours, 1.5 hours, 3 hours and 5 hours, thus evaluating the amount of reduction of hexanal to the passage of time. In this case, since cucurbit[7]uril is hardly volatilized due to its high molecular weight, the amount of reduction of hexanal was relatively quantitated by the integration ratio of NMR peak of cucurbit[7]uril and NMR peak of hexanal. When a fragrant material (hexanal) existed alone, the amount of reduction of the fragrant material (hexanal) was evaluated based on methanesulfonic acid under the condition that cucurbit[7]uril does not exist. The results thereof are shown in FIG. 9.

As shown in FIG. 9, it can be seen that, when hexanal existed alone, it took 1.5 hours (red full line) to completely release hexanal, but when hexanal was formed into a complex together with cucurbit[7]uril, only 45% of hexanal was released during 5 hours (blue full line). From the experimental results, it can be ascertained that, when hexanal was formed into a complex together with cucurbit[7]uril, the reduction rate of hexanal became very low compared to when hexanal existed alone.

5-2: Evaluation of release rate of fragrant molecule in dry state

100 mg of cucurbit[7]uril and 7.6 mg of hexanal were put into a mortar. Subsequently, 0.5 mL of distilled water was added to the mortar to form a slurry, and then the slurry was stirred for 10 minutes using a pestle to prepare complex samples. The complex samples were dried in an oven at 40℃ for 6 hours. Some of the dried complex samples were immediately measured by 1H-NMR, and others thereof were respectively charged in two 20 mL glass vials, and were then left at room temperature or 40℃. In this case, air is introduced into each of the vials such that air is sufficiently circulated therein. After 2 days, the amount of residual hexanal was evaluated by 1H-NMR measurement. The experimental results thereof are shown in FIG. 10.

From the experimental results shown in FIG. 10, it can be seen that the amount of hexanal bonded with cucurbit[7]uril was hardly reduced at room temperature for 2 days in the dry state. Further, it can be seen that, even when the experiment was carried out at 40℃ or more, the amount thereof was not reduced at all. That is, it can be seen that the release of hexanal from cucurbit[7]uril is very restricted in the dry state regardless of temperature.

Although the preferred embodiments of the present invention have been disclosed for illustrative purposes, those skilled in the art will appreciate that various modifications, additions and substitutions are possible, without departing from the scope and spirit of the invention as disclosed in the accompanying claims.

The composition is advantageous in that the fragrant molecule is more slowly released when it exists in the form of a complex compared to when it exists alone. Therefore, when a product including this complex is manufactured, the reduction of a fragrant material due to the long-term storage thereof can be minimized, and a fragrant material can be released for a long period of time compared to conventional products. Accordingly, it is presumed that this composition will be applied to air cleaning and environment improvement.

Claims

A composition for slowly releasing a fragrant molecule, the composition comprising a complex of a fragrant molecule and a compound represented by Chemical Formula 1 below:

[Chemical Formula 1]

wherein n is an integer of 4 to 20, and X is O, S or NH, and

wherein the composition comprises 45 to 100 wt% of the compound of Chemical Formula 1 of n = 7.
The composition of claim 1, wherein the complex of a compound of Chemical Formula 1 and a fragrant molecule has a molar ratio of the compound to the fragrant molecule of 1: 0.5 ~ 1.
The composition of claim 1, wherein the fragrant molecule is selected from the group consisting of ethyl butyrate, camphor, menthol, hexanal, eugenol, citronellol, linalool, patchoulol, santalol, phenyl ethyl alcohol, terpineol, vanillin, benzaldehyde, methyl salicylate, isoamyl acetate, d-limonene, L-limonene, α-pinene, 2-hydroxy-p-cymene, methyl acetophenone, and cis-jasmone.
The composition of claim 1, further comprising water.