EP1470761B1 - Smoking filter and smoking article - Google Patents

Smoking filter and smoking article Download PDF

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Publication number
EP1470761B1
EP1470761B1 EP03701015.4A EP03701015A EP1470761B1 EP 1470761 B1 EP1470761 B1 EP 1470761B1 EP 03701015 A EP03701015 A EP 03701015A EP 1470761 B1 EP1470761 B1 EP 1470761B1
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EP
European Patent Office
Prior art keywords
filter
acid
cigarette
hydrotalcite
hydrotalcite compound
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP03701015.4A
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German (de)
English (en)
French (fr)
Other versions
EP1470761A1 (en
EP1470761A4 (en
Inventor
Takashi c/o JAPAN TOBACCO INC. SASAKI
Masafumi c/o JAPAN TOBACCO INC. TARORA
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Japan Tobacco Inc
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Japan Tobacco Inc
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Filing date
Publication date
Application filed by Japan Tobacco Inc filed Critical Japan Tobacco Inc
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Publication of EP1470761A4 publication Critical patent/EP1470761A4/en
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Publication of EP1470761B1 publication Critical patent/EP1470761B1/en
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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
    • 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
    • A24D3/16—Use of materials for tobacco smoke filters of inorganic materials
    • 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
    • A24D3/062—Use of materials for tobacco smoke filters characterised by structural features
    • A24D3/063—Use of materials for tobacco smoke filters characterised by structural features of the fibers
    • 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
    • A24D3/08—Use of materials for tobacco smoke filters of organic materials as carrier or major constituent
    • A24D3/10—Use of materials for tobacco smoke filters of organic materials as carrier or major constituent of cellulose or cellulose derivatives
    • 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
    • A24D3/12—Use of materials for tobacco smoke filters of ion exchange materials

Definitions

  • the present invention relates to a smoking filter and a smoking article.
  • the adsorbent used in the past also adsorbs the components other than formaldehyde, with the result that it was possible for adverse effects to be given to the flavor and taste of the smoking article.
  • JP 2001 300220 A discloses an air cleaning filter apparatus constituted of a first filter obtained by supporting acidic phosphate and a copper compound on a base material and a second filter obtained by supporting a hydrotalcite compound and a sulfite on a base material.
  • EP-A-0 532 329 discloses cigarettes including a filter element which have a gathered web of paper incorporating a carbonaceous material. The paper is gathered so as to include a plurality of longitudinally extending channels, and the channels provide a cross-sectional void area of about 5 to about 30 percent of the filter element.
  • An object of the present invention is to provide a smoking filter and a smoking article capable of selectively removing formaldehyde contained in mainstream smoke.
  • the present invention is directed to a cigarette, characterized by comprising:
  • a smoking filter for a cigarette i.e. a cigarette filter containing a hydrotalcite compound exhibiting a lamellar structure in which a large number of octahedral layers of a metal hydroxide are laminated one upon the other.
  • the hydrotalcite compound used in the present invention is represented by a general formula: M 2+ 1-x M 3+ x (OH) 2 (A n- ) x/n • mH 2 O
  • M 2+ represents a divalent metal ion selected from the group consisting of a Mg ion, a Zn ion, a Ni ion and a Ca ion
  • M 3+ represents an Al ion
  • the cigarette filter is prepared by dispersing a hydrotalcite compound having an average particle diameter falling within a range of between 200 ⁇ m and 800 ⁇ m in, for example, the fiber tow or an unwoven fabric sheet.
  • the typical fiber used in the present invention is formed of cellulose acetate.
  • the cigarette filter prefferably be prepared by forming a paper sheet added with a hydrotalcite compound having an average particle diameter not larger than 10 ⁇ m.
  • the cigarette filter prefferably includes a plurality of filter segments, at least one filter segment containing a hydrotalcite compound.
  • a charcoal filter segment in addition to the filter segment containing the hydrotalcite compound.
  • the cigarette filter prefferably includes a plurality of filter segments and hydrotalcite particles filled in the space present between the adjacent filter segments.
  • a smoking article including the cigarette filter referred to above and a tobacco rod connected to the smoking filter.
  • hydrotalcite compounds permit effectively removing formaldehyde.
  • the hydrotalcite compound exhibits a lamellar structure in which a large number of octahedral layers of a divalent or trivalent metal hydroxide are laminated one upon the other, and an anion is intercalated in the octahedral layers.
  • the octahedral layer is referred to as a host and exhibits basicity. It is considered reasonable to understand that the removal of formaldehyde achieved by the hydrotalcite compound results from contribution of the basicity of the host and from the ion exchange function performed by the intercalated anions.
  • hydrotalcite compound is represented by a general formula: M 2+ 1-x M 3+ x (OH) 2 (A n- ) x/n • mH 2 O.
  • a Mg ion constitutes the divalent metal ion M 2+ included in the general formula given above
  • an Al ion constitutes the trivalent metal ion M 3+
  • CO 3 2- or SO 4 2- constitutes the anion A n- .
  • a Zn ion, a Ni ion or a Ca ion to constitute the divalent metal ion M 2+ in addition to the Mg ion.
  • the anion is selected from the group consisting of OOC-COO, Cl, Br, F, NO 3 , Fe(CN) 6 3- , Fe(CN) 6 4- , phthalic acid, isophthalic acid, terephthalic acid, maleic acid, alkenyl acid and its derivative, malic acid, salicylic acid, acrylic acid, adipic acid, succinic acid, citric acid and sulfonic acid in addition to CO 3 2- and SO 4 2- .
  • the symbol x in the general formula is larger than 0.1 and smaller than 0.4, i.e., 0.1 ⁇ x ⁇ 0.4, and the symbol m is larger than 0 and smaller than 2, i.e., 0 ⁇ m ⁇ 2.
  • the Mg-Al-based hydrotalcite compound is stable in the case where the value of x falls within a range of between 0.20 and 0.33.
  • a reaction is carried out by adding an alkali carbonate or both an alkali carbonate and a caustic alkali to an aqueous solution containing a water-soluble aluminum salt selected from the group consisting of aluminum sulfate, aluminum acetate and aluminum potassium sulfate or aluminic acid and a water-soluble magnesium salt while maintaining the pH value of the reaction mixture at 8.0 or more.
  • a water-soluble aluminum salt selected from the group consisting of aluminum sulfate, aluminum acetate and aluminum potassium sulfate or aluminic acid and a water-soluble magnesium salt
  • hydrotalcite compound it is possible to control a micro pore size of the hydrotalcite compound by, for example, the size of the anion intercalated in the hydrotalcite compound. It is also possible for the hydrotalcite compound to perform various functions depending on the nature of the anion and on the state of the interlayer water.
  • the hydrotalcite compound it is desirable to control the particle diameter of the hydrotalcite compound as follows.
  • the hydrotalcite compound it is desirable for the hydrotalcite compound to have a particle diameter of 200 to 800 ⁇ m, more desirably 400 to 600 ⁇ m.
  • the hydrotalcite compound it is desirable for the hydrotalcite compound to have a particle diameter not larger than 10 ⁇ m.
  • a hydrotalcite compound represented by Mg 6 Al 2 (OH) 16 CO 3 •4H 2 O was used.
  • the particle diameter of the hydrotalcite compound was controlled to 250 to 500 ⁇ m by pulverization and sieving.
  • a filter 1 shown in FIG. 1 was prepared by using the hydrotalcite compound.
  • a hydrotalcite powder 3 was filled in the space present between two acetate filter segments 2, 2 each wrapped with a plug wrapper and, then, the resultant structure was wrapped with a forming paper 4 so as to prepare the filter 1 of the plug-space-plug structure.
  • filters of the plug-space-plug structure as shown in FIG. 1 were prepared by using following adsorbents: charcoal, charcoal having a high specific surface area, alkali metal salt impregnated charcoal, amine impregnated charcoal, active alumina, magnesium oxide, aluminum oxide, magnesium silicate, zinc oxide, silica gel, zeolite, construction material pulp for formalin, a column packing material for gas chromatography (GC), and water-absorbing resin.
  • adsorbents charcoal, charcoal having a high specific surface area, alkali metal salt impregnated charcoal, amine impregnated charcoal, active alumina, magnesium oxide, aluminum oxide, magnesium silicate, zinc oxide, silica gel, zeolite, construction material pulp for formalin, a column packing material for gas chromatography (GC), and water-absorbing resin.
  • the amount of formaldehyde contained in cigarette mainstream smoke was measured according to "Health Canada - Official Method" (2,4-DNPH-HPLC method) so as to provide the removal rate of formaldehyde.
  • DNPH 2,4-dinitrophenyl hydrazine
  • a DNPH trapping solution 12 is put in a Drechsel-type trap 11.
  • the Drechsel-type trap 11 has an inner volume of 100 mL, and an amount of the DNPH trapping solution 12 is 80 mL.
  • the trap 11 is put in an ice water bath 13 so as to be cooled.
  • the lower end of a glass pipe 14 to which a cigarette 10 is attached is dipped in the trapping solution 12 within the trap 11.
  • a glass pipe 15 having a Cambridge pad 16 mounted thereto is arranged to communicate with the dead volume of the trap 11, and a smoking machine 17 was connected to the Cambridge pad 16.
  • the cigarette 10 was attached to the glass pipe 14 so as to permit the cigarette 10 to be automatically smoked under the standard smoking conditions specified in ISO standards. To be more specific, the operation of sucking 35 mL of the smoke in a single puff for two seconds for a single cigarette was repeated at an interval of 58 seconds. While the mainstream smoke was being bubbled, formaldehyde was converted into a derivative of DNPH. Two cigarettes were used for the measurement. In this case, the cigarettes using the different adsorbents were controlled to exhibit the same pressure loss.
  • the formaldehyde derivative thus formed was measured by high-performance liquid chromatography (HPLC).
  • HPLC high-performance liquid chromatography
  • the trapping solution was filtered, followed by diluting the filtered trapping solution with a Trizma Base solution (4 mL of trapping solution : 6 mL of Trizma Base solution). Then, the diluted solution was measured by the HPLC.
  • the measuring conditions of the HPLC were as follows:
  • FIG. 3 is a graph showing the removal rates of formaldehyde in the case of using various adsorbents. As apparent from FIG. 3 , formaldehyde was most effectively removed in the case of using hydrotalcite as the adsorbent.
  • the removal rate of the vapor phase components contained in cigarette mainstream smoke was measured by using as an adsorbent a hydrotalcite compound or charcoal constituting the most general adsorbent for a cigarette.
  • a filter similar to that shown in FIG. 1 was manufactured as in Example 1 by preparing a hydrotalcite compound having a particle diameter of 250 to 500 ⁇ m or charcoal as an adsorbent and loading the adsorbent in an amount of 50 mg. Then, a cigarette was prepared by connecting a tobacco section containing 12 mg of tar to the filter thus manufactured.
  • FIG. 4 shows the trapping method of the vapor phase components.
  • a cigarette 10 was attached to a smoking machine 17 so as to permit the cigarette 10 to be automatically smoked under the standard smoking conditions specified in the ISO standards.
  • the particle phase in the mainstream smoke was removed by a Cambridge filter, and the vapor phase was trapped by a gas bag 20.
  • the operation of sucking 35 mL of the smoke in 2 seconds in a single puff for each cigarette was repeated at an interval of 58 seconds.
  • 10 conditioned cigarettes (conditioned under temperature of 22°C and humidity of 60%) were automatically smoked.
  • FIG. 5 shows gas chromatography.
  • a prescribed amount of the vapor phase components trapped in the gas bag 20 is stored in a sample loop 21.
  • the vapor phase components are injected into a gas chromatograph 22.
  • the components are separated in a column (DB-WAX) and detected in a detector. Further, the amounts of the components are analyzed by using a program installed in a personal computer 23. The analytical value was obtained by dividing the peak area of each of the vapor phase components by the peak area of the standard gas.
  • FIG. 6 is a graph showing the relationship between the vapor pressure of the vapor phase component and the removal rate of the component.
  • the removal rate is increased with increase in the vapor pressure of the vapor phase component in the case of using charcoal as an adsorbent.
  • the removal rate is specifically high in respect of formaldehyde, supporting that the hydrotalcite compound permits selectively removing formaldehyde.
  • the hydrotalcite compound is granulated, it is possible to prepare samples differing from each other in the particle size distribution. In this case, the samples are classified depending on the average particle diameter of the hydrotalcite compound.
  • FIG. 7A shows three types of samples having the average particle diameters of 250 ⁇ m, 500 ⁇ m, and 800 ⁇ m, respectively.
  • Filters of the construction as shown in FIG. 1 were prepared by using hydrotalcite particles differing from each other in the average particle diameter. These filters differed from each other in the loading amount of the hydrotalcite particles.
  • filters of the construction shown in FIG. 1 were also prepared by using charcoal. These filters also differed from each other in the loading amount of the charcoal.
  • the resistance to draw was examined in respect of these filters under the sucking flow rate of 1050 mL/min.
  • the resistance to draw was calculated by excluding the resistance to draw due to the two acetate filter segments 2, 2 shown in FIG. 1 .
  • FIG. 7B is a graph showing the relationship between the average particle diameter and the resistance to draw. As apparent from FIG. 7B , the resistance to draw is high in the case of using the adsorbent particles having the average particle diameter of 250 ⁇ m and is low in the case of using the adsorbent particles having the average particle diameter of 800 ⁇ m. FIG. 7B also indicates that it is reasonable to use hydrotalcite particles having the average particle diameter falling within a range of between 400 ⁇ m and 600 ⁇ m in designing cigarettes.
  • hydrotalcite particles having a desired size it is possible to provide hydrotalcite particles having a desired size by employing any granulating method such as rolling granulation, compression molding, coating granulation, or extrusion molding. It should be noted in this connection that, in order to avoid the breakage of the hydrotalcite particles in the manufacturing process of the filter, it is desirable to employ a granulating method that permits manufacturing granulated hydrotalcite particles having an appropriate hardness. The present inventor found that it is possible to prevent the hydrotalcite particles from being broken in the manufacturing process of the filter if the hydrotalcite particles have a hardness falling within a range of between 300 g/mm 2 and 3,000 g/mm 2 .
  • This Example is intended to support that the reduction rate of the formaldehyde content in mainstream smoke achieved by the hydrotalcite particle is dependent on the surface area of the hydrotalcite particle.
  • Various granulated hydrotalcite particles were prepared by means of (A) rolling granulation, (B) compression molding, and (C) extrusion molding.
  • the average surface area per unit weight of the hydrotalcite particles was calculated by using a laser scattering type particle size distribution measuring apparatus.
  • FIG. 8 is a graph showing the result.
  • This Example is intended to examine the reduction rate of formaldehyde contained in mainstream smoke, which is achieved by a paper filter to which hydrotalcite particles are added, and by a cellulose acetate filter to which granulated hydrotalcite particles are added.
  • a paper sheet was made while adding hydrotalcite particles having an average particle diameter not larger than 10 ⁇ m. Then, the paper filter 7 shown in FIG. 9 was prepared by using the resultant paper sheet. For comparison, a filter was prepared by forming a paper sheet to which hydrotalcite particles were not added.
  • a filter was also prepared by dispersing granulated hydrotalcite particles in the cellulose acetate tow.
  • a cellulose acetate filter was prepared without using hydrotalcite particles.
  • the filters thus prepared were 25 mm long and were made as uniform as possible in the resistance to draw.
  • the ratio of formaldehyde outflow to tar outflow was decreased in the paper filter containing the hydrotalcite particles, compared with the acetate filter containing the hydrotalcite particles. It is considered reasonable to understand that the result was achieved by the large contact surface area of the hydrotalcite particles having an average particle diameter not larger than 10 ⁇ m dispersed in the paper filter.
  • This Example is intended to support that the reduction rate of the organic vapor components can be increased by the combination of a hydrotalcite filter and a charcoal filter.
  • Filters I, II, III of the triple segment structure including an acetate filter segment, a hydrotalcite (HT) filter segment and a charcoal filter segment as shown in Table 2 were prepared.
  • the acetate filter segment was prepared by bundling cellulose acetate tow and was 7 mm long.
  • the hydrotalcite (HT) filter segment was prepared by bundling cellulose acetate tow having 70 mg of hydrotalcite particles dispersed therein and was 10 mm long.
  • the charcoal filter segment was prepared by bundling cellulose acetate tow having 70 mg of charcoal particles dispersed therein and was 10 mm long.
  • FIG. 10 shows the construction of the filter III shown in Table 2.
  • a charcoal filter segment 5 is arranged on the side of the cut tobacco
  • an acetate filter segment is arranged on the inhaling side
  • an HT filter segment 6 is arranged intermediate between the charcoal filter segment 5 and the acetate filter segment 2.
  • the filter III permits lowering the content of the total organic vapor because of the function of the charcoal filter and also permits lowering the formaldehyde content because of the function of the hydrotalcite (HT) filter.
  • Table 2 Cut tobacco side Center Inhaling side TOV reduction rate (%) FA reduction rate (%) I charcoal filter acetate filter acetate filter 62.7 67.2 II acetate filter HT filter acetate filter 20.8 69.3 III charcoal filter HT filter acetate filter 64.8 71.9 Weight of additives: 70 mg/10 mm Filter length: 10mm, 10mm, and 7mm Ventilation resistance of filter tip: 72 mmWG/27 mm Ventilation hole: no
  • the filter of the construction as shown in FIG. 1 it is possible to use another filter segment in place of at least one of the acetate filter segments 2.
  • a hydrotalcite filter segment or a charcoal filter segment in place of at least one of the acetate filter segments 2.
  • the cellulose acetate tow having a hydrotalcite compound dispersed therein were used for forming the hydrotalcite filter segment.
  • a hydrotalcite filter segment prepared by forming a paper sheet made by adding hydrotalcite compound was also possible.
  • a filter comprising a charcoal filter segment 5, a space filled with hydrotalcite particles 3, a hydrotalcite (HT) filter segment 6 and an acetate filter segment 2, as shown in FIG. 11 .
  • the hydrotalcite filter segment 6 it is possible for the hydrotalcite filter segment 6 to be acetate filter-based or paper filter-based in this case, too. It is possible for the arrangement of the space filled with the HT particles 3 and the HT filter segment 6 to be opposite to that shown in FIG. 11 . In FIG. 11 , the space is filled with HT particles. Alternatively, it is possible for the space to be filled with charcoal particles.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Inorganic Chemistry (AREA)
  • Cigarettes, Filters, And Manufacturing Of Filters (AREA)
  • Solid-Sorbent Or Filter-Aiding Compositions (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Filtering Materials (AREA)
EP03701015.4A 2002-01-08 2003-01-07 Smoking filter and smoking article Expired - Lifetime EP1470761B1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP2002001509 2002-01-08
JP2002001509 2002-01-08
PCT/JP2003/000036 WO2003056947A1 (fr) 2002-01-08 2003-01-07 Filtre anti-fumee et article a fumer

Publications (3)

Publication Number Publication Date
EP1470761A1 EP1470761A1 (en) 2004-10-27
EP1470761A4 EP1470761A4 (en) 2009-05-27
EP1470761B1 true EP1470761B1 (en) 2015-12-30

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Application Number Title Priority Date Filing Date
EP03701015.4A Expired - Lifetime EP1470761B1 (en) 2002-01-08 2003-01-07 Smoking filter and smoking article

Country Status (15)

Country Link
US (1) US20040237983A1 (ko)
EP (1) EP1470761B1 (ko)
JP (1) JP3895327B2 (ko)
KR (1) KR100912311B1 (ko)
CN (2) CN1612701A (ko)
AU (1) AU2003202479A1 (ko)
CA (1) CA2472385C (ko)
DK (1) DK1470761T3 (ko)
ES (1) ES2563032T3 (ko)
MY (1) MY146655A (ko)
PT (1) PT1470761E (ko)
RU (1) RU2291657C2 (ko)
TW (1) TWI324049B (ko)
UA (1) UA77052C2 (ko)
WO (1) WO2003056947A1 (ko)

Cited By (2)

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CN110639283A (zh) * 2019-09-16 2020-01-03 江苏清荷材料科技有限公司 一种采用凹土复合材料制备空气滤网的方法
RU2739544C1 (ru) * 2017-06-19 2020-12-25 Джапан Тобакко Инк. Фильтр курительного изделия и способ его изготовления

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JP5623875B2 (ja) 2010-11-11 2014-11-12 株式会社ダイセル 複合粒子、タバコフィルター及びその製造方法並びにタバコ
EP2540174B1 (en) 2011-06-29 2017-06-21 Daicel Corporation Tobacco Filter Containing Magnesium Aluminometasilicate
RU2604020C2 (ru) * 2011-12-06 2016-12-10 Джапан Тобакко Инк. Сигаретный фильтр и сигарета
CN102551206A (zh) * 2012-01-04 2012-07-11 安徽中烟工业有限责任公司 一种可降低卷烟主流烟气有害成分释放量的含层状双氢氧化物的卷烟滤嘴
JP6575993B2 (ja) * 2015-05-25 2019-09-18 住江織物株式会社 アンモニアガス、二酸化硫黄ガス及び二酸化窒素ガス除去フィルター
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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2739544C1 (ru) * 2017-06-19 2020-12-25 Джапан Тобакко Инк. Фильтр курительного изделия и способ его изготовления
CN110639283A (zh) * 2019-09-16 2020-01-03 江苏清荷材料科技有限公司 一种采用凹土复合材料制备空气滤网的方法

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JPWO2003056947A1 (ja) 2005-05-12
CN1612701A (zh) 2005-05-04
AU2003202479A1 (en) 2003-07-24
WO2003056947A1 (fr) 2003-07-17
US20040237983A1 (en) 2004-12-02
EP1470761A1 (en) 2004-10-27
CA2472385C (en) 2011-08-02
PT1470761E (pt) 2016-03-18
ES2563032T3 (es) 2016-03-10
CN102028307A (zh) 2011-04-27
CA2472385A1 (en) 2003-07-17
RU2291657C2 (ru) 2007-01-20
KR20040073534A (ko) 2004-08-19
TW200301681A (en) 2003-07-16
JP3895327B2 (ja) 2007-03-22
EP1470761A4 (en) 2009-05-27
TWI324049B (en) 2010-05-01
MY146655A (en) 2012-09-14
UA77052C2 (en) 2006-10-16
KR100912311B1 (ko) 2009-08-14
RU2004124060A (ru) 2006-01-27
DK1470761T3 (en) 2016-02-15

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