Patent Application
20080264433
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.
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 μm. 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.
The present invention provides a tobacco producing a reduced amount of a harmful component and a method of preparing the same.
According to an aspect of the present invention, there is provided a tobacco filter including 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 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-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, A1 and A2 may be each H, and n may be an integer of 5 to 12.
X may be O, A1 and A2 may be each OH, and n may be an integer of 5 to 12.
X may be O, A1 and A2 may be each O—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:
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 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-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;
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 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-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 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:
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 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-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 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:
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 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-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 the present invention, a tobacco producing a reduced amount of a harmful component and a method of preparing the same are provided.
The present invention will now be described more fully with reference to the accompanying drawings, in which exemplary embodiments of the invention are shown.
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
Referring to
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 (S16).
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.
Referring to
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 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-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 0, A1 and A2 may be each H, and n may be an integer of 5 to 12.
Alternatively, X may be 0, A1 and A2 may be each OH, and n may be an integer of 5 to 12.
Still alternatively, X may be 0, A1 and A2 may be each O—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 [Acc. 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
Cucurbiturils are also denoted as cucurbit[n]urils where n is as defined in Formula 1 above.
Referring to
The current embodiment of the present invention is different from the previous embodiment shown in
Tobaccos according to the embodiments shown in
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.
100 mg of a cucurbit[5]uril powder of Formula 1 where X was 0, and A1 and A2 were each H was finely pulverized and incorporated into the filters of commercially available tobaccos (THIS™, KT&G™) as shown in
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 15 ml of ethylacetate and distilled under a reduced pressure. The residues were dissolved in 100 μl 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 (8/100 mesh). A column temperature was 100° C., nitrogen was used as a carrier gas, and a flow rate was 60 ml/min.
The experimental results are presented in Table 1 below.
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.
The results of Table 2 show that cucurbiturils can reduce the emission of CO and NO gases from tobacco filters.
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.
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.
Measurement of CO and NO Concentration in Gaseous Matter Passed Through 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.
The results of Table 4 show that cucurbiturils can reduce the emission of CO and NO gases from tobacco filters.
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.
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.
Measurement of CO and NO Concentration in Gaseous Matter Passed Through 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.
The results of Table 6 show that cucurbiturils can reduce the emission of CO and NO gases from tobacco filters.
Tobacco samples were prepared in the same manner as in Example 1 except that cucurbit[6]uril of Formula 1 where X was 0 and A1 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.
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.
Measurement of CO and NO Concentration in Gaseous Matter Passed Through 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.
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.
| Filing Document | Filing Date | Country | Kind | 371c Date |
|---|---|---|---|---|
| PCT/KR2006/000841 | 3/9/2006 | WO | 00 | 4/25/2008 |
