WO2007102634A1 - Cucurbituril added cigarettes and manufacturing method thereof - Google Patents
Cucurbituril added cigarettes and manufacturing method thereof Download PDFInfo
- Publication number
- WO2007102634A1 WO2007102634A1 PCT/KR2006/000841 KR2006000841W WO2007102634A1 WO 2007102634 A1 WO2007102634 A1 WO 2007102634A1 KR 2006000841 W KR2006000841 W KR 2006000841W WO 2007102634 A1 WO2007102634 A1 WO 2007102634A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- substituted
- unsubstituted
- tobacco
- crc
- integer
- Prior art date
Links
Classifications
-
- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24D—CIGARS; CIGARETTES; TOBACCO SMOKE FILTERS; MOUTHPIECES FOR CIGARS OR CIGARETTES; MANUFACTURE OF TOBACCO SMOKE FILTERS OR MOUTHPIECES
- A24D1/00—Cigars; Cigarettes
- A24D1/002—Cigars; Cigarettes with additives, e.g. for flavouring
-
- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24D—CIGARS; CIGARETTES; TOBACCO SMOKE FILTERS; MOUTHPIECES FOR CIGARS OR CIGARETTES; MANUFACTURE OF TOBACCO SMOKE FILTERS OR MOUTHPIECES
- A24D3/00—Tobacco smoke filters, e.g. filter-tips, filtering inserts; Filters specially adapted for simulated smoking devices; Mouthpieces for cigars or cigarettes
- A24D3/06—Use of materials for tobacco smoke filters
- A24D3/14—Use of materials for tobacco smoke filters of organic materials as additive
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Cigarettes, Filters, And Manufacturing Of Filters (AREA)
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 >
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 >
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:
<Formula 1 >
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 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-
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:
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:
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:
<Formula 1>
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.
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.
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.
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.
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.
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.
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:
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:
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:
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:
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 CrC3O, a substituted or unsubstituted alkoxy of C1-C30, a substituted or unsubstituted hydroxyalkyl of Ci-C30, a substituted or unsubstituted alkylsilyl of Ci-C3O, 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-C3O, 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.
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP06716291A EP1942752A4 (en) | 2006-03-09 | 2006-03-09 | Cucurbituril added cigarettes and manufacturing method thereof |
PCT/KR2006/000841 WO2007102634A1 (en) | 2006-03-09 | 2006-03-09 | Cucurbituril added cigarettes and manufacturing method thereof |
KR1020087002687A KR100964503B1 (en) | 2006-03-09 | 2006-03-09 | Cucurbituril added cigarettes and manufacturing method thereof |
US12/091,557 US20080264433A1 (en) | 2006-03-09 | 2006-03-09 | Cucurbituril Added Cigarettes and Manufacturing Method Thereof |
JP2008541059A JP4931931B2 (en) | 2006-03-09 | 2006-03-09 | Tobacco added with cucurbituril and method for producing the same |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/KR2006/000841 WO2007102634A1 (en) | 2006-03-09 | 2006-03-09 | Cucurbituril added cigarettes and manufacturing method thereof |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2007102634A1 true WO2007102634A1 (en) | 2007-09-13 |
Family
ID=38475050
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/KR2006/000841 WO2007102634A1 (en) | 2006-03-09 | 2006-03-09 | Cucurbituril added cigarettes and manufacturing method thereof |
Country Status (5)
Country | Link |
---|---|
US (1) | US20080264433A1 (en) |
EP (1) | EP1942752A4 (en) |
JP (1) | JP4931931B2 (en) |
KR (1) | KR100964503B1 (en) |
WO (1) | WO2007102634A1 (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104059077A (en) * | 2014-07-08 | 2014-09-24 | 贵州大学 | Substituent group hexahydric cucurbitnuril and preparation method thereof |
CN104151459A (en) * | 2014-08-12 | 2014-11-19 | 贵州大学 | Quinary, senary or octonary cucurbituril bridged acrylic acid polymer and preparation method thereof |
CN104193867A (en) * | 2014-08-12 | 2014-12-10 | 贵州大学 | Seven-membered cucurbit urils bridged acrylic polymer and preparation method and application thereof |
CN104592240A (en) * | 2015-01-05 | 2015-05-06 | 贵州大学 | Seven-membered cucurbituril bridged acrylic acid naphthol ester as well as preparation method and application thereof |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102008008018A1 (en) * | 2008-02-07 | 2009-08-27 | Daimler Ag | Vehicle window and motor vehicle with a vehicle window |
CN106666826B (en) * | 2017-02-24 | 2019-11-19 | 江西中烟工业有限责任公司 | A kind of melon ring additive and preparation method thereof of pair of Harm reduction techniques flavouring |
CN114057690B (en) * | 2021-11-30 | 2024-02-27 | 昆明理工大学 | Clathrate compound of semi-cucurbit [6] urils and tobacco alkaloids, and preparation method and application thereof |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2527234A1 (en) | 1974-06-21 | 1976-01-08 | Kiichi Arakawa | CIGARETTE FILTER |
WO1999039595A1 (en) * | 1998-02-09 | 1999-08-12 | Rousseau Research, Inc. | Tobacco products with vitamin e |
WO2003013286A1 (en) * | 2001-08-02 | 2003-02-20 | Japan Tobacco Inc. | Filter for cigarette |
WO2003013287A1 (en) * | 2001-08-02 | 2003-02-20 | Japan Tobacco Inc. | Filter for cigarette |
WO2003055888A1 (en) | 2002-01-03 | 2003-07-10 | Postech Foundation | Hydroxycucurbituril derivatives, their preparation methods and uses |
DE10300083A1 (en) | 2002-02-12 | 2003-08-21 | Ufl Umweltanalytik Und Forschu | Cigarette filter for absorbing harmful substances containing active carbon and cyclodextrin useful for decreasing the level of harmful substances inhaled by smokers |
WO2003092416A1 (en) * | 2002-04-27 | 2003-11-13 | British American Tobacco (Investments) Limited | Improvements relating to smoking articles and smokable filler materials therefor |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE60007257T2 (en) * | 1999-10-21 | 2004-09-16 | Pohang University Of Science And Technology Foundation, Pohang | Process for the preparation of cucurbituril derivatives |
US7152609B2 (en) * | 2003-06-13 | 2006-12-26 | Philip Morris Usa Inc. | Catalyst to reduce carbon monoxide and nitric oxide from the mainstream smoke of a cigarette |
-
2006
- 2006-03-09 WO PCT/KR2006/000841 patent/WO2007102634A1/en active Application Filing
- 2006-03-09 JP JP2008541059A patent/JP4931931B2/en not_active Expired - Fee Related
- 2006-03-09 US US12/091,557 patent/US20080264433A1/en not_active Abandoned
- 2006-03-09 EP EP06716291A patent/EP1942752A4/en not_active Withdrawn
- 2006-03-09 KR KR1020087002687A patent/KR100964503B1/en not_active IP Right Cessation
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2527234A1 (en) | 1974-06-21 | 1976-01-08 | Kiichi Arakawa | CIGARETTE FILTER |
WO1999039595A1 (en) * | 1998-02-09 | 1999-08-12 | Rousseau Research, Inc. | Tobacco products with vitamin e |
WO2003013286A1 (en) * | 2001-08-02 | 2003-02-20 | Japan Tobacco Inc. | Filter for cigarette |
WO2003013287A1 (en) * | 2001-08-02 | 2003-02-20 | Japan Tobacco Inc. | Filter for cigarette |
WO2003055888A1 (en) | 2002-01-03 | 2003-07-10 | Postech Foundation | Hydroxycucurbituril derivatives, their preparation methods and uses |
KR20030060053A (en) * | 2002-01-03 | 2003-07-12 | 학교법인 포항공과대학교 | Hydroxy cucrubiturils and their derivatives, their preparation methods and uses |
DE10300083A1 (en) | 2002-02-12 | 2003-08-21 | Ufl Umweltanalytik Und Forschu | Cigarette filter for absorbing harmful substances containing active carbon and cyclodextrin useful for decreasing the level of harmful substances inhaled by smokers |
WO2003092416A1 (en) * | 2002-04-27 | 2003-11-13 | British American Tobacco (Investments) Limited | Improvements relating to smoking articles and smokable filler materials therefor |
Non-Patent Citations (3)
Title |
---|
MIYAHARA ET AL., ANGEW. CHEM., vol. 114, no. 16, 2002, pages 3146 - 3149 |
MIYAHARA Y., ABE K., INAZU T.: ""Molecular" Molecular Sieves: Lid-Free Decamethylcucurbit[5]uril Absorbes and Desorbs Gases Selectively", ANGREW. CHEM. INT. ED., vol. 41, no. 16, 2002, pages 3020 - 3023, XP008120926 * |
See also references of EP1942752A4 * |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104059077A (en) * | 2014-07-08 | 2014-09-24 | 贵州大学 | Substituent group hexahydric cucurbitnuril and preparation method thereof |
CN104151459A (en) * | 2014-08-12 | 2014-11-19 | 贵州大学 | Quinary, senary or octonary cucurbituril bridged acrylic acid polymer and preparation method thereof |
CN104193867A (en) * | 2014-08-12 | 2014-12-10 | 贵州大学 | Seven-membered cucurbit urils bridged acrylic polymer and preparation method and application thereof |
CN104592240A (en) * | 2015-01-05 | 2015-05-06 | 贵州大学 | Seven-membered cucurbituril bridged acrylic acid naphthol ester as well as preparation method and application thereof |
Also Published As
Publication number | Publication date |
---|---|
KR100964503B1 (en) | 2010-06-21 |
KR20080047348A (en) | 2008-05-28 |
US20080264433A1 (en) | 2008-10-30 |
JP4931931B2 (en) | 2012-05-16 |
EP1942752A4 (en) | 2013-01-16 |
EP1942752A1 (en) | 2008-07-16 |
JP2009515549A (en) | 2009-04-16 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US7025067B2 (en) | Activated charcoal filter for effectively reducing p-benzosemiquinone from the mainstream cigarette smoke | |
JP5161585B2 (en) | Cigarette with filter | |
RU2577838C2 (en) | Smoking article comprising alkanoylated glucoside and method for production thereof | |
WO2007102634A1 (en) | Cucurbituril added cigarettes and manufacturing method thereof | |
RU2048780C1 (en) | Smoking composition and a method of its producing | |
CN103054181B (en) | Coffee or cocoa composite particle filtering bar and manufacturing method thereof | |
WO2003013285A1 (en) | A filtering material for cigarette and its process to use ginkgo leaf ingredients | |
EP2517584A1 (en) | Composite filter comprising biological composition | |
US5000198A (en) | Agent for removing noxious tobacco components | |
Yamamoto et al. | Effect of cigarette circumference on formation rates of various components in mainstream smoke | |
JPH08505051A (en) | Filter cigarette | |
JPH06121664A (en) | Cigaret filter | |
Cvetkovic et al. | Catalytic reduction of NO and NOx content in tobacco smoke | |
WO2008155674A2 (en) | Smoking articles and method for treating tobacco material with a suspension containing bismuth containing compounds and optionally glycerin | |
JP2016502847A (en) | Aluminosilicate SAB-15 as an additive to reduce toxic and carcinogenic compounds present in cigarette smoke | |
US3842070A (en) | Filtering material | |
Haustein et al. | Tobacco constituents and additives | |
Hegde et al. | A Study to Determine the Nicotine Concentration and pH in Commercially Available Brands of Cigarettes and Bidis. | |
CN113598412A (en) | Composite filter tip for adsorbing 2-acetylpyridine in cigarette smoke and cigarette | |
KR20060019441A (en) | Method of a tobacco |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
WWE | Wipo information: entry into national phase |
Ref document number: 1020087002687 Country of ref document: KR |
|
WWE | Wipo information: entry into national phase |
Ref document number: 12091557 Country of ref document: US |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2006716291 Country of ref document: EP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2008541059 Country of ref document: JP |
|
NENP | Non-entry into the national phase |
Ref country code: DE |