EP1942752A1

EP1942752A1 - Cucurbituril added cigarettes and manufacturing method thereof

Info

Publication number: EP1942752A1
Application number: EP06716291A
Authority: EP
Inventors: Kimoon Kim; Kyeng-Min Park; Young-Ho Ko; Narayanan Selvapalam
Original assignee: POSTECH Academy Industry Foundation
Current assignee: POSTECH Academy Industry Foundation
Priority date: 2006-03-09
Filing date: 2006-03-09
Publication date: 2008-07-16
Also published as: JP4931931B2; EP1942752A4; WO2007102634A1; JP2009515549A; KR20080047348A; KR100964503B1; US20080264433A1

Abstract

Provided is a cucurbituril-containing tobacco. The cucurbituril-containing tobacco includes a cucurbituril represented by Formula 1. The cucurbituril-containing tobacco can produce a reduced amount of harmful substances.

Description

CUCURBITURIL ADDED CIGARETTES AND MANUFACTURING METHOD

THEREOF

TECHNICAL FIELD

The present invention relates to a cucurbituril-containing tobacco and a method of preparing the same, and more particularly, to a tobacco producing a reduced amount of a harmful component and a method of preparing the same.

BACKGROUND ART

Generally, tobacco is leaf tobacco that has been processed to a state suitable for smoking, chewing, etc. Tobacco is mostly designed for smoking, and thus, can be classified into cigarette, cigar, cut tobacco, etc. Cigarette is the most common form of tobacco, and thus, tobacco is commonly referred to as "cigarette". Tobacco contains a large amount of harmful substances, and thus, excessive smoking can cause serious health problems. In this regard, the regulation for prohibition of smoking in public places was recently designed and has been gradually strengthened.

The relationship between smoking and disease has been actively studied from the mid 1900's, and many evidences of an association between smoking and a high incidence of various diseases (e.g., lung cancer) or other health problems have been accumulated. About 4,000 components of tobacco smoke have been identified, which constitute about 95% by volume or more of tobacco smoke, and the remaining 5% is made up of a trace amount of components. Tobacco smoke is produced during incomplete combustion of tobacco.

Complete combustion of tobacco produces only water and carbon dioxide. The incomplete combustion of tobacco results from incomplete combustibility of some of tobacco leaf components, insufficient oxygen supply, and local temperature difference during tobacco combustion. The combustion of tobacco is a process involving distillation, sublimation, thermal decomposition, thermal synthesis, and volatilization. Tobacco smoke is an aerosol in which liquid or particulate materials are suspended in a gaseous phase, and the gaseous phase is defined as a gaseous or vapor component that passes through the Cambridge glass-fiber filter capable of retaining 99% or more of particulate materials with a particle size greater than 0.1 //Hi. The gaseous or vapor component is composed of nitrogen (59%), oxygen (13.4%), carbon dioxide (13.5%), carbon monoxide (3.2%), etc. The gaseous or vapor component also contains a low molecular weight volatile component that inhibits a bronchial ciliary action, e.g., aldehyde, ketone, alcohol, and ester.

A material that is trapped when smoke stream flows through the Cambridge glass-fiber filter is defined as a particulate-phase component. The particulate-phase component constitutes about 8% of tobacco smoke and contains at least 38 known carcinogens (e.g., tar), substances with carcinogenic potentiality, nicotine, and many other inorganic or organic chemicals.

Korean Patent Laid-Open Publication No. 2005-0083035 and No. 1999-0031164 disclose a tobacco filter including an activated carbon, zeolite particles, an adsorptive powder, etc. to minimize the inhalation of harmful components of tobacco smoke. However, these techniques are unsatisfactory to reduce the inhalation of harmful components of tobacco smoke.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 is a flow diagram illustrating a method of preparing a cucurbituril- containing tobacco according to an embodiment of the present invention;

FIG. 2 is a transmitted perspective view illustrating a cucurbituril-containing tobacco according to an embodiment of the present invention; and

FIG. 3 is a transmitted perspective view illustrating a cucurbituril-containing tobacco according to another embodiment of the present invention.

DETAILED DESCRIPTION OF THE INVENTION Technical Goal of the Invention

The present invention provides a tobacco producing a reduced amount of a harmful component and a method of preparing the same.

Disclosure of the Invention

According to an aspect of the present invention, there is provided a tobacco filter including a cucurbituril represented by Formula 1 below: <Formula 1 >

wherein X is O, S, or NH;

Ai and A₂ are each H or respectively OR¹ and OR², SR¹ and SR², or NHR¹ and NHR² where R¹ and R² are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl of Ci-C₃₀, a substituted or unsubstituted alkenyl of Ci-C₃₀, a substituted or unsubstituted alkynyl of CrC₃₀, a substituted or unsubstituted carbonylalkyl of C₂-C₃₀, a substituted or unsubstituted thioalkyl of Ci-C₃₀, a substituted or unsubstituted alkylthiol of CrC₃₀, a substituted or unsubstituted alkoxy of CrC₃₀, a substituted or unsubstituted hydroxyalkyl of CrC₃₀, a substituted or unsubstituted alkylsilyl of CrC₃₀, a substituted or unsubstituted aminoalkyl of CrC₃₀, a substituted or unsubstituted aminoalkylthioalkyl of CrC₃₀, a substituted or unsubstituted cycloalkyl of C₅-C₃₀, a substituted or unsubstituted heterocycloalkyl of C₂-C₃₀, a substituted or unsubstituted aryl of C₆-C₃₀, a substituted or unsubstituted arylalkyl of C₆- C₂₀, a substituted or unsubstituted heteroaryl of C₄-C₃₀, and a substituted or unsubstituted heteroarylalkyl Of C₄-C₂₀; and n is an integer of 4 to 20.

X may be O, Ai and A₂ may be each H, and n may be an integer of 5 to 12. X may be O, Ai and A₂ may be each OH, and n may be an integer of 5 to 12. X may be O, Ai and A₂ may be each 0-CH₂-CH=CH₂, and n may be an integer of 5 to 12.

According to another aspect of the present invention, there is provided a tobacco including: a tobacco rod prepared by wrapping a processed leaf tobacco with a cigarette paper; and a tobacco filter, attached to a side of the tobacco rod to filter out a harmful component, including a cucurbituril represented by Formula 1 below: <Formula 1 >

wherein X is O, S, or NH;

A₁ and A₂ are each H or respectively OR¹ and OR², SR¹ and SR², or NHR¹ and

NHR² where R¹ and R² are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl of Ci-C₃₀, a substituted or unsubstituted alkenyl of C₁-C₃₀, a substituted or unsubstituted alkynyl of C1-C30, a substituted or unsubstituted carbonylalkyl of C₂-C₃₀, a substituted or unsubstituted thioalkyl of Ci-C₃₀, a substituted or unsubstituted alkylthiol of Ci-C₃₀, a substituted or unsubstituted alkoxy of Ci-C₃₀, a substituted or unsubstituted hydroxyalkyl of C₁-C₃₀, a substituted or unsubstituted alkylsilyl of CrC₃₀, a substituted or unsubstituted aminoalkyl of CrC₃₀, a substituted or unsubstituted aminoalkylthioalkyl of CrC₃₀, a substituted or unsubstituted cycloalkyl of C₅-C₃₀, a substituted or unsubstituted heterocycloalkyl of C₂-C₃₀, a substituted or unsubstituted aryl of C₆-C₃₀, a substituted or unsubstituted arylalkyl of C₆-

C₂₀, a substituted or unsubstituted heteroaryl of C₄-C₃₀, and a substituted or unsubstituted heteroarylalkyl of C₄-C₂₀; and n is an integer of 4 to 20.

According to still another aspect of the present invention, there is provided a tobacco including: a tobacco rod prepared by wrapping a processed leaf tobacco with a cigarette paper; a tobacco filter attached to a side of the tobacco rod to filter out a harmful component; and a cucurbituril, interposed between the tobacco rod and the tobacco filter, being represented by Formula 1 below:

wherein X is O, S, or NH;

NHR² where R¹ and R² are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl of Ci-C₃₀, a substituted or unsubstituted alkenyl of Ci-C₃₀, a substituted or unsubstituted alkynyl of CrC₃₀, a substituted or unsubstituted carbonylalkyl of C₂-C₃₀, a substituted or unsubstituted thioalkyl of Ci-C₃₀, a substituted or unsubstituted alkylthiol of CrC₃₀, a substituted or unsubstituted alkoxy of CrC₃₀, a substituted or unsubstituted hydroxyalkyl of CrC₃₀, a substituted or unsubstituted alkylsilyl of CrC₃₀, a substituted or unsubstituted aminoalkyl of CrC₃₀, a substituted or unsubstituted aminoalkylthioalkyl of CrC₃₀, a substituted or unsubstituted cycloalkyl of C₅-C₃₀, a substituted or unsubstituted heterocycloalkyl of C₂-C₃₀, a substituted or unsubstituted aryl of Ce-C₃₀, a substituted or unsubstituted arylalkyl of CQ-

According to yet another aspect of the present invention, there is provided a method of preparing a tobacco, the method including: blending, processing, and cutting tobacco leaves and wrapping the resultant product with a cigarette paper to prepare a tobacco rod; preparing a tobacco filter containing a cucurbituril represented by Formula

1 below; and assembling the tobacco rod and the tobacco filter:

<Formula 1> wherein X is O, S, or NH;

NHR² where R¹ and R² are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl of C₁-C₃₀, a substituted or unsubstituted alkenyl of C₁-C₃₀, a substituted or unsubstituted alkynyl of C₁-C₃₀, a substituted or unsubstituted carbonylalkyl of C₂-C₃₀, a substituted or unsubstituted thioalkyl of C₁-C₃₀, a substituted or unsubstituted alkylthiol of C₁-C₃₀, a substituted or unsubstituted alkoxy of C₁-C₃₀, a substituted or unsubstituted hydroxyalkyl of C₁-C₃₀, a substituted or unsubstituted alkylsilyl of C₁-C₃₀, a substituted or unsubstituted aminoalkyl of C₁-C₃₀, a substituted or unsubstituted aminoalkylthioalkyl of C₁-C₃₀, a substituted or unsubstituted cycloalkyl of C₅-C₃₀, a substituted or unsubstituted heterocycloalkyl of C₂-C₃₀, a substituted or unsubstituted aryl of C₆-C₃₀, a substituted or unsubstituted arylalkyl of C₆-

According to a further aspect of the present invention, there is provided a method of preparing a tobacco, the method including: blending, processing, and cutting tobacco leaves and wrapping the resultant product with a cigarette paper to prepare a tobacco rod; preparing a tobacco filter; preparing a cucurbituril represented by Formula

1 below; and assembling the tobacco rod, the tobacco filter, and the cucurbituril:

<Formula 1 > wherein X is O, S, or NH;

A₁ and A₂ are each H or respectively OR¹ and OR², SR¹ and SR², or NHR¹ and NHR² where R¹ and R² are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl of CrC₃₀, a substituted or unsubstituted alkenyl of C₁-C₃₀, a substituted or unsubstituted alkynyl of C1-C₃₀, a substituted or unsubstituted carbonylalkyl of C₂-C₃0, a substituted or unsubstituted thioalkyl of C1-C30, a substituted or unsubstituted alkylthiol of CrC₃₀, a substituted or unsubstituted alkoxy of C₁-C₃₀, a substituted or unsubstituted hydroxyalkyl of CrC₃₀, a substituted or unsubstituted alkylsilyl of C₁-C₃₀, a substituted or unsubstituted aminoalkyl of CrC₃₀, a substituted or unsubstituted aminoalkylthioalkyl of C₁-C₃₀, a substituted or unsubstituted cycloalkyl of C₅-C₃₀, a substituted or unsubstituted heterocycloalkyl of C₂-C₃₀, a substituted or unsubstituted aryl of C₆-C₃₀, a substituted or unsubstituted arylalkyl of C₆- C₂₀, a substituted or unsubstituted heteroaryl of C₄-C₃₀, and a substituted or unsubstituted heteroarylalkyl of C₄-C₂o; and n is an integer of 4 to 20.

Effect of the Invention

According to the present invention, a tobacco producing a reduced amount of a harmful component and a method of preparing the same are provided.

BEST MODE FOR CARRYING OUT THE INVENTION

The present invention will now be described more fully with reference to the accompanying drawings, in which exemplary embodiments of the invention are shown. FIG. 1 is a flow diagram illustrating a method of preparing a cucurbituril- containing tobacco according to an embodiment of the present invention.

Hereinafter, a method of preparing a cucurbituril-containing tobacco according to an embodiment of the present invention will be described in detail with reference to FIG. 1.

Referring to FIG. 1 , first, various tobacco leaves are blended (S10). In operation S10, various tobacco leaves with distinctive flavors, tastes, or colors are blended to give final tobacco products with a characteristic flavor, taste, or color.

Next, the blend of the tobacco leaves is processed (S12). This operation involves fermentation, heating, flavoring, defect removal, etc. to enhance the commercial value of tobacco products. The blend of the tobacco leaves may also be humidified or heated to soften the tobacco leaves. Next, the processed tobacco leaves are cut into leaf pieces with an appropriate size (S14). The leaf pieces are transported to a tobacco-manufacturing machine (not shown).

Next, the leaf pieces are wrapped with a cigarette paper to obtain a filter-free tobacco rod (S 16). On the other hand, a tobacco filter is separately prepared (S30). At this time, a cucurbituril may be incorporated to the tobacco filter (S40). The content of the cucurbituril may be 1-99 parts by weight, more preferably 25-75 parts by weight, based on 100 parts by weight of the tobacco filter. If the content of the cucurbituril is less than 1 part by weight, the removal efficiency of a harmful component may be lowered. On the other hand, if it exceeds 99 parts by weight, a cucurbituril powder may be insufficiently supported by the tobacco filter.

Next, the tobacco rod and the tobacco filter are assembled (S18). At this time, a cucurbituril may also be incorporated between the tobacco rod and the tobacco filter, without being incorporated into the tobacco filter (S40). Finally, thus-prepared separate tobaccos are encased to thereby obtain final tobacco products (S20).

Cucurbiturils were first reported by R. Behrend, E. Meyer, and F. Rusche in

1905. In early 2000, Ki-Moon Kim and coworkers reported the improved preparation and separation of well-known cucurbit[6]uril and its homologues, cucurbit[n]urils (n = 5, 7, 8) and identified their X-ray crystal structures [J. Am. Chem. Soc. 2000, 122, 540].

Cucurbiturils will be specifically described later.

FIG. 2 is a transmitted perspective view illustrating a cucurbituril-containing tobacco according to an embodiment of the present invention. Referring to FIG. 2, a tobacco 10 includes a tobacco rod 11 and a tobacco filter 12.

The tobacco rod 11 is prepared by wrapping a blend of tobacco leaves with a cigarette paper, as described above. The tobacco filter 12 includes a first filter portion 12a contacting with the tobacco rod 11 , a third filter portion 12c contacting with the mouth of a smoker, and a second filter portion 12b interposed between the first filter portion 12a and the third filter portion 12c.

The first filter portion 12a and the third filter portion 12c are common fiber filters, and may be made of the same material or different materials.

The second filter portion 12b includes a cucurbituril represented by Formula 1 below:

wherein X is O, S, or NH;

A₁ and A₂ are each H or respectively OR¹ and OR², SR¹ and SR², or NHR¹ and NHR² where R¹ and R² are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl of C₁-C₃₀, a substituted or unsubstituted alkenyl of CrC₃₀, a substituted or unsubstituted alkynyl of Ci-C₃₀, a substituted or unsubstituted carbonylalkyl of C₂-C₃₀, a substituted or unsubstituted thioalkyl of C₁-C₃₀, a substituted or unsubstituted alkylthiol of Ci-C₃₀, a substituted or unsubstituted alkoxy of C₁-C₃₀, a substituted or unsubstituted hydroxyalkyl of CrC₃₀, a substituted or unsubstituted alkylsilyl of CrC₃₀, a substituted or unsubstituted aminoalkyl of CrC₃₀, a substituted or unsubstituted aminoalkylthioalkyl of C₁-C₃₀, a substituted or unsubstituted cycloalkyl of C₅-C₃₀, a substituted or unsubstituted heterocycloalkyl of C₂-C₃₀, a substituted or unsubstituted aryl of Ce-C₃₀, a substituted or unsubstituted arylalkyl of C₆- C₂₀, a substituted or unsubstituted heteroaryl of C₄-C₃₀, and a substituted or unsubstituted heteroarylalkyl of C₄-C₂₀; and n is an integer of 4 to 20. Specifically, X may be O, Ai and A₂ may be each H, and n may be an integer of 5 to 12.

Alternatively, X may be O, Ai and A₂ may be each OH, and n may be an integer of 5 to 12. Still alternatively, X may be O, A₁ and A₂ may be each 0-CH₂-CH=CH₂, and n may be an integer of 5 to 12.

The above-described cucurbiturils and cucurbituril derivatives are compounds consisting of unsubstituted glycoluril monomer units. Cucurbituril derivatives consisting of substituted glycoluril monomer units are also known [Angew, Chem. Int. Ed. Engl. 1992, 31 , 1475]. Hereinafter, cucurbiturils and cucurbituril derivatives will be commonly referred to simply as "cucurbiturils".

Cucurbiturils are macrocyclic compounds and have a lipophilic cavity and two hydrophilic entrances at upper and lower portions. In this respect, lipophilic interactions occur in the cavity of cucurbiturils, and hydrogen bonds, polar-polar interactions, and positive charge-polar interactions occur in the two entrances having six carbonyl groups. Therefore, cucurbiturils have retention capacity for various compounds by a very stable non-covalent linkage with these compounds. Cucurbiturils form a very stable non-covalent linkage, in particular, with compounds having a functional group such as an alkyl group, an amino group, or a carboxyl group, alkaline metals, heavy metals, or amine group-containing gaseous compounds. Based on such characteristics, studies about application of cucurbiturils in various areas have been continuously conducted.

Cucurbiturils are host molecules having cavities therein, and can form a non- covalent linkage with guest molecules to produce host-guest complexes [Ace. Chem. Res. 2003, 36, 621]. Furthermore, cucurbiturils also have adsorption capability to various molecules capable of non-covalently binding with the cucurbiturils, and harmful gases, such as CO and NOx, [Angew. Chem. Int. Ed. 2002, 41, 3020]. Thus, cucurbiturils can be used to filter out specific molecules or gas components. In this regard, the incorporation of cucurbituril homologues, derivatives, or mixtures into conventional tobacco filters can promote the filtration, deodorization, neutralization, or removal of harmful substances, such as nicotine, tar, nicoteline, anabasin, CO, NO, and NOx, in tobacco smoke, thereby minimizing the inhalation of the harmful substances.

Recently, while studying the utility of cucurbiturils as drug delivery systems, the present inventors developed a hydroxycucurbituril wherein an active substituent (i.e., a hydroxy group) is introduced into a cucurbituril as represented by Formula 1 above (see Korean Patent Laid-Open Publication No. 2003-60053).

Various substituents can be easily introduced into the above-described hydroxycucurbituril, which enables the synthesis of various cucurbituril derivatives.

Referring again to FIG. 2, the second filter portion 12b may include one or more cucurbiturils represented by Formula 1 above.

Cucurbiturils are also denoted as cucurbit[n]urils where n is as defined in Formula 1 above. FIG. 2 illustrates that the cucurbituril-containing second filter portion 12b is formed separately from the first and third filter portions 12a and 12c, but the present invention is not limited thereto. The second filter portion 12b may also be formed integrally with the first and third filter portions 12a and 12c. In this case, the cucurbituril is dispersed in the first and third filter portions 12a and 12c. FIG. 3 is a transmitted perspective view illustrating a cucurbituril-containing tobacco according to another embodiment of the present invention.

Referring to FIG. 3, a tobacco 20 includes a tobacco rod 21 , a tobacco filter 22, and a cucurbituril 23.

The current embodiment of the present invention is different from the previous embodiment shown in FIG. 2 except that the cucurbituril 23 is not contained in the tobacco filter 22 but interposed between the tobacco rod 21 and the tobacco filter 22.

Tobaccos according to the embodiments shown in FIGS. 2 and 3 are prepared in different manners due to their structural difference. That is, the preparation of a tobacco according to the embodiment shown in FIG. 2 includes preparing a tobacco rod, preparing a cucurbituril-containing tobacco filter, and assembling the tobacco rod and the tobacco filter, whereas the preparation of a tobacco according to the embodiment shown in FIG. 3 includes preparing a tobacco rod, preparing a tobacco filter, preparing a cucurbituril, and assembling the tobacco rod, the tobacco filter, and the cucurbituril.

That is, in the preparation of a tobacco according to the embodiment shown in FIG. 2, cucurbituril incorporation occurs during the preparation of the tobacco filter. On the other hand, in the preparation of a tobacco according to the embodiment shown in FIG.

3, cucurbituril incorporation occurs during assembling a tobacco rod and a tobacco filter.

Hereinafter, the present invention will be described more specifically with reference to the following working examples. The following working examples are for illustrative purposes and are not intended to limit the scope of the present invention.

Examples

Example 1

Tobacco preparation

100 mg of a cucurbit[5]uril powder of Formula 1 where X was O, and Ai and A₂ were each H was finely pulverized and incorporated into the filters of commercially available tobaccos (THIS™, KT&G™) as shown in FIG. 2 to thereby prepare tobacco samples.

Measurement of nicotine concentration in tobacco filters

The tobacco samples were loaded into pipes and smoked. Then, tobacco filters were separated and the concentration of nicotine in the tobacco filters was measured as follows. That is, the tobacco filters were extracted with about 15ml of ethylacetate and distilled under a reduced pressure. The residues were dissolved in 100μβ of ethylacetate, and the resultant solutions were used as test samples. The test samples were analyzed by gas chromatography (HP 5890 with FID, U.S.A) on a glass column (2 m in length and 3 mm in diameter) packed with 2% Tharmon 1000 + 1 % KOH chromosorb WAM (8/100mesh). A column temperature was 100^°C , nitrogen was used as a carrier gas, and a flow rate was 60 m^/min.

The experimental results are presented in Table 1 below.

Table 1

A: tobacco filter with no cucurbituril B: tobacco filter with cucurbituril

As shown in Table 1 , the cucurbituril-containing tobacco filters retained a larger amount of nicotine than the cucurbituril-free tobacco filters. This result shows that cucurbiturils can reduce the emission of nicotine from tobacco filters.

Measurement of CO and NO concentration in gaseous matter passed through tobacco filters

Tobacco smoke, which had passed through the tobacco filters, was collected, and the concentration of CO and NO in the tobacco smoke was measured using a gas analyzer (UniGas 3000+, Eurotron, Italy).

The experimental results are presented in Table 2 below.

Table 2

A: tobacco filter with no cucurbituril B: tobacco filter with cucurbituril

The results of Table 2 show that cucurbiturils can reduce the emission of CO and NO gases from tobacco filters.

Example 2 Tobacco preparation

Tobacco samples were prepared in the same manner as in Example 1 except that cucurbit[7]uril was used instead of the cucurbit[5]uril.

Measurement of nicotine concentration in tobacco filters The concentration of nicotine in the filters of the above-prepared tobacco samples was measured in the same manner as in Example 1 , and the results are presented in Table 3 below. Table 3

A: tobacco filter with no cucurbituril B: tobacco filter with cucurbituril

As shown in Table 3, the cucurbituril-containing tobacco filters retained a larger amount of nicotine than the cucurbituril-free tobacco filters. This result shows that cucurbiturils can reduce the emission of nicotine from tobacco filters.

Like in Example 1 , tobacco smoke, which had passed through the tobacco filters, was collected, and the concentration of CO and NO in the tobacco smoke was measured. The results are presented in Table 4 below.

Table 4

A: tobacco filter with no cucurbituril B: tobacco filter with cucurbituril

The results of Table 4 show that cucurbiturils can reduce the emission of CO and NO gases from tobacco filters.

Example 3 Tobacco preparation

Tobacco samples were prepared in the same manner as in Example 1 except that a mixture of cucurbit[5]uril, cucurbit[6]uril, cucurbit[7]uril, and cucurbit[8]uril (weight ratio: 1 :1 :1 :1 ) was used instead of the cucurbit[5]uril.

Measurement of nicotine concentration in tobacco filters

The concentration of nicotine in the filters of the above-prepared tobacco samples was measured in the same manner as in Example 1 , and the results are presented in Table 5 below. Table 5

A: tobacco filter with no cucurbituril B: tobacco filter with cucurbituril

As shown in Table 5, the cucurbituril-containing tobacco filters retained a larger amount of nicotine than the cucurbituril-free tobacco filters. This result shows that cucurbiturils can reduce the emission of nicotine from tobacco filters.

Like in Example 1 , tobacco smoke, which had passed through the tobacco filters, was collected, and the concentration of CO and NO in the tobacco smoke was measured. The results are presented in Table 6 below.

Table 6

A: tobacco filter with no cucurbituril B: tobacco filter with cucurbituril

The results of Table 6 show that cucurbiturils can reduce the emission of CO and NO gases from tobacco filters.

Example 4 Tobacco preparation

Tobacco samples were prepared in the same manner as in Example 1 except that cucurbit[6]uril of Formula 1 where X was O and Ai and A₂ were each OH was used instead of the cucurbit[5]uril.

Measurement of nicotine concentration in tobacco filters

The concentration of nicotine in the filters of the above-prepared tobacco samples was measured in the same manner as in Example 1 , and the results are presented in Table 7 below. Table 7

A: tobacco filter with no cucurbituril B: tobacco filter with cucurbituril

As shown in Table 7, the cucurbituril-containing tobacco filters retained a larger amount of nicotine than the cucurbituril-free tobacco filters. This result shows that cucurbiturils can reduce the emission of nicotine from tobacco filters.

Like in Example 1 , tobacco smoke, which had passed through the tobacco filters, was collected, and the concentration of CO and NO in the tobacco smoke was measured. The results are presented in Table 8 below.

Table 8

A: tobacco filter with no cucurbituril B: tobacco filter with cucurbituril

The results of Table 8 show that cucurbiturils can reduce the emission of CO and NO gases from tobacco filters.

The above experimental examples have been illustrated in terms of the filtering effects of cucurbiturils on nicotine and CO/NO gas among harmful substances of tobacco. However, cucurbiturils, when incorporated into conventional tobacco filters, can also promote the filtration, deodorization, neutralization, or removal of other harmful substances, such as tar, nicoteline, and anabasin, thereby minimizing the inhalation of harmful substances during smoking.

While the present invention has been particularly shown and described with reference to exemplary embodiments thereof, it will be understood by those of ordinary skill in the art that various changes in form and details may be made therein without departing from the spirit and scope of the present invention as defined by the following claims.

Claims

1. A tobacco filter comprising a cucurbituril represented by Formula 1 below:

wherein X is O, S, or NH;

Ai and A₂ are each H or respectively OR¹ and OR², SR¹ and SR², or NHR¹ and NHR² where R¹ and R² are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl of C-₁-C₃₀, a substituted or unsubstituted alkenyl of Ci-C₃₀, a substituted or unsubstituted alkynyl of C-1-C30, a substituted or unsubstituted carbonylalkyl of C₂-C₃₀, a substituted or unsubstituted thioalkyl of C₁-C₃₀, a substituted or unsubstituted alkylthiol of CrC₃₀, a substituted or unsubstituted alkoxy of Ci-C₃₀, a substituted or unsubstituted hydroxyalkyl of Ci-C₃₀, a substituted or unsubstituted alkylsilyl of CrC₃₀, a substituted or unsubstituted aminoalkyl of CrC₃₀, a substituted or unsubstituted aminoalkylthioalkyl of CrC₃₀, a substituted or unsubstituted cycloalkyl of C₅-C₃₀, a substituted or unsubstituted heterocycloalkyl of C₂-C₃₀, a substituted or unsubstituted aryl of C₆-C₃₀, a substituted or unsubstituted arylalkyl of C₆- C₂₀, a substituted or unsubstituted heteroaryl of C₄-C₃₀, and a substituted or unsubstituted heteroarylalkyl of C₄-C₂₀; and n is an integer of 4 to 20.

2. The tobacco filter of claim 1 , wherein X is O, Ai and A₂ are each H, and n is an integer of 5 to 12.

3. The tobacco filter of claim 1 , wherein X is O, A₁ and A₂ are each OH, and n is an integer of 5 to 12.

4. The tobacco filter of claim 1 , wherein X is O, Ai and A₂ are each 0-CH₂- CH=CH₂, and n is an integer of 5 to 12.

5. A tobacco comprising: a tobacco rod prepared by wrapping a processed leaf tobacco with a cigarette paper; and a tobacco filter, attached to a side of the tobacco rod to filter out a harmful component, comprising a cucurbituril represented by Formula 1 below:

wherein X is O, S, or NH;

Ai and A₂ are each H or respectively OR¹ and OR², SR¹ and SR², or NHR¹ and NHR² where R¹ and R² are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl of C₁-C₃₀, a substituted or unsubstituted alkenyl of C₁-C₃₀, a substituted or unsubstituted alkynyl of Ci-C₃₀, a substituted or unsubstituted carbonylalkyl of C₂-C₃₀, a substituted or unsubstituted thioalkyl of Ci-C₃₀, a substituted or unsubstituted alkylthiol of Ci-C₃₀, a substituted or unsubstituted alkoxy of CrC₃₀, a substituted or unsubstituted hydroxyalkyl of CrC₃₀, a substituted or unsubstituted alkylsilyl of CrC₃₀, a substituted or unsubstituted aminoalkyl of CrC₃₀, a substituted or unsubstituted aminoalkylthioalkyl of CrC₃₀, a substituted or unsubstituted cycloalkyl of C₅-C₃₀, a substituted or unsubstituted heterocycloalkyl of C₂-C₃₀, a substituted or unsubstituted aryl of C₆-C₃₀, a substituted or unsubstituted arylalkyl of C₆- C₂₀, a substituted or unsubstituted heteroaryl of C₄-C₃₀, and a substituted or unsubstituted heteroarylalkyl of C₄-C₂₀; and n is an integer of 4 to 20.

6. The tobacco of claim 5, wherein X is O, Ai and A₂ are each H, and n is an integer of 5 to 12.

7. The tobacco of claim 5, wherein X is O, Ai and A₂ are each OH, and n is an integer of 5 to 12.

8. The tobacco of claim 5, wherein X is O, Ai and A₂ are each 0-CH₂-

CH=CH₂, and n is an integer of 5 to 12.

9. A tobacco comprising: a tobacco rod prepared by wrapping a processed leaf tobacco with a cigarette paper; a tobacco filter attached to a side of the tobacco rod to filter out a harmful component; and a cucurbituril, interposed between the tobacco rod and the tobacco filter, being represented by Formula 1 below:

wherein X is O, S, or NH;

Ai and A₂ are each H or respectively OR¹ and OR², SR¹ and SR², or NHR¹ and NHR² where R¹ and R² are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl of C₁-C₃₀, a substituted or unsubstituted alkenyl of C₁-C₃₀, a substituted or unsubstituted alkynyl of CrC₃₀, a substituted or unsubstituted carbonylalkyl of C₂-C₃₀, a substituted or unsubstituted thioalkyl of C1-C30, a substituted or unsubstituted alkylthiol of C₁-C₃₀, a substituted or unsubstituted alkoxy of C₁-C₃₀, a substituted or unsubstituted hydroxyalkyl of CrC₃₀, a substituted or unsubstituted alkylsilyl of CrC₃₀, a substituted or unsubstituted aminoalkyl of C₁-C3Q, a substituted or unsubstituted aminoalkylthioalkyl of CrC₃₀, a substituted or unsubstituted cycloalkyl of C₅-C₃₀, a substituted or unsubstituted heterocycloalkyl of C₂-C₃₀, a substituted or unsubstituted aryl of Ce-C₃₀, a substituted or unsubstituted arylalkyl of C₆- C₂O, a substituted or unsubstituted heteroaryl of C4-C30, and a substituted or unsubstituted heteroarylalkyl of C₄-C2o; and n is an integer of 4 to 20.

10. The tobacco of claim 9, wherein X is O, Ai and A₂ are each H, and n is an integer of 5 to 12.

11. The tobacco of claim 9, wherein X is O, Ai and A₂ are each OH, and n is an integer of 5 to 12.

12. The tobacco of claim 9, wherein X is O, Ai and A₂ are each 0-CH₂- CH=CH₂, and n is an integer of 5 to 12.

13. A method of preparing a tobacco, the method comprising: blending, processing, and cutting tobacco leaves, and wrapping the resultant product with a cigarette paper to prepare a tobacco rod; preparing a tobacco filter containing a cucurbituril represented by Formula 1 below; and assembling the tobacco rod and the tobacco filter:

wherein X is O, S, or NH;

Ai and A₂ are each H or respectively OR¹ and OR², SR¹ and SR², or NHR¹ and NHR² where R¹ and R² are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl of C₁-C₃₀, a substituted or unsubstituted alkenyl of C₁-C₃₀, a substituted or unsubstituted alkynyl of C₁-C₃₀, a substituted or unsubstituted carbonylalkyl of C₂-C₃₀, a substituted or unsubstituted thioalkyl of Ci-C₃₀, a substituted or unsubstituted alkylthiol of CrC_3O, a substituted or unsubstituted alkoxy of C₁-C₃₀, a substituted or unsubstituted hydroxyalkyl of Ci-C₃₀, a substituted or unsubstituted alkylsilyl of Ci-C_3O, a substituted or unsubstituted aminoalkyl of Ci-C₃₀, a substituted or unsubstituted aminoalkylthioalkyl of Ci-C₃₀, a substituted or unsubstituted cycloalkyl of C₅-C₃₀, a substituted or unsubstituted heterocycloalkyl of C₂-C₃₀, a substituted or unsubstituted aryl of Ce-C₃₀, a substituted or unsubstituted arylalkyl of Cβ- C₂₀, a substituted or unsubstituted heteroaryl of C₄-C₃₀, and a substituted or unsubstituted heteroarylalkyl of C₄-C₂₀; and n is an integer of 4 to 20.

14. The method of claim 13, wherein X is O, Ai and A₂ are each H, and n is an integer of 5 to 12.

15. The method of claim 13, wherein X is O, Ai and A₂ are each OH, and n is an integer of 5 to 12.

16. The method of claim 13, wherein X is O, Ai and A₂ are each 0-CH₂- CH=CH₂, and n is an integer of 5 to 12.

17. A method of preparing a tobacco, the method comprising: blending, processing, and cutting tobacco leaves, and wrapping the resultant product with a cigarette paper to prepare a tobacco rod; preparing a tobacco filter; preparing a cucurbituril represented by Formula 1 below; and assembling the tobacco rod, the tobacco filter, and the cucurbituril:

wherein X is O, S, or NH; Ai and A₂ are each H or respectively OR¹ and OR², SR¹ and SR², or NHR¹ and NHR² where R¹ and R² are each independently selected from the group consisting of hydrogen, a substituted or unsubstituted alkyl of Ci-C₃₀, a substituted or unsubstituted alkenyl of C1-C3₀, a substituted or unsubstituted alkynyl of C1-C₃₀, a substituted or unsubstituted carbonylalkyl of C₂-C_3O, a substituted or unsubstituted thioalkyl of Ci-C₃₀, a substituted or unsubstituted alkylthiol of CrC₃₀, a substituted or unsubstituted alkoxy of Ci-C₃₀, a substituted or unsubstituted hydroxyalkyl of CrC₃₀, a substituted or unsubstituted alkylsilyl of CrC₃₀, a substituted or unsubstituted aminoalkyl of CrC₃₀, a substituted or unsubstituted aminoalkylthioalkyl of CrC₃₀, a substituted or unsubstituted cycloalkyl of Cs-C₃₀, a substituted or unsubstituted heterocycloalkyl of C₂-C₃₀, a substituted or unsubstituted aryl of C₆-C₃₀, a substituted or unsubstituted arylalkyl of C₆- C₂₀, a substituted or unsubstituted heteroaryl of C₄-C₃₀, and a substituted or unsubstituted heteroarylalkyl Of C₄-C₂₀; and n is an integer of 4 to 20.

18. The method of claim 17, wherein X is O, Ai and A₂ are each H, and n is an integer of 5 to 12.

19. The method of claim 17, wherein X is O, Ai and A₂ are each OH, and n is an integer of 5 to 12.

20. The method of claim 17, wherein X is O, Ai and A₂ are each 0-CH₂- CH=CH₂, and n is an integer of 5 to 12.