US3470883A - Tobacco smoke filters - Google Patents

Tobacco smoke filters Download PDF

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Publication number
US3470883A
US3470883A US756128A US3470883DA US3470883A US 3470883 A US3470883 A US 3470883A US 756128 A US756128 A US 756128A US 3470883D A US3470883D A US 3470883DA US 3470883 A US3470883 A US 3470883A
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Prior art keywords
tobacco
polymer
cigarette
filter
acid
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Expired - Lifetime
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US756128A
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English (en)
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Thomas H Shepherd
Francis E Gould
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National Patent Development Corp
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National Patent Development Corp
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    • 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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S521/00—Synthetic resins or natural rubbers -- part of the class 520 series
    • Y10S521/905—Hydrophilic or hydrophobic cellular product

Definitions

  • Tobacco smoke filters are prepared from a porous, hydrophilic acrylate or methacrylate polymer having a pore volume of at least 60%.
  • the pores are conveniently formed by polymerizing in aqueous medium and freeze drying or by polymerizing with or without water utilizing a foaming agent to form a hard, friable foam.
  • the present invention relates to tobacco smoke filters and more particularly to the removal from tobacco smoke tars which may contain undesirable components such as carcinogenic substances therein.
  • Carcinogenesis the causing of cancerous growth in living tissue, is a complex process. Many factors are involved; some related to the host and others to the agent. Some agents by themselves cause irreversible alterations in cells which may lead to the production of cancer; others promote the carcinogenic process. The former are called initiators; the latter, promoters.
  • cigarette smoke for example, is a heterogeneous mixture of gases, uncondensed vapors, and liquid particulate material.
  • One important factor determining the composition of the smoke is the temperature in the burning zone. While air is being drawn through a cigarette, the temperature of the burning zone may reach approximately 884 C. and when the cigarette is burned in the absence of air being drawn therethrough, the temperature is approximately 835 C. At these temperatures, extensive pyrolytic reactions occur in the tobacco adjacent to the burning zone. Some of the many constituents of tobacco are stable enough to distill unchanged, but many others suffer extensive reactions involving oxidation, dehydrogenation, cracking, rearrangement, and condensation. It is thus not surprising that some 500 different compounds have been identified in the smoke.
  • Another object of this invention is to provide a process for producing such filter elements.
  • Still another object of the invention is to provide a tobacco filter element which enhances removal of carcinogens formed during combustion of said tobacco.
  • a further object of the invention is to prepare a porous hydrophilic polymer.
  • the polymer has a high surface area and a pore volume preferably in the range of 60 to The surface area is usually between 10 and 300 meters2/gram.
  • the pores are preferably formed by freeze drying the polymer which has been formed in the presence of water.
  • the freeze drying is usually done at -5 to -30 ⁇ C. Lower temperatures can be used but the process is slower.
  • the drying or desiccation is preferably done in a vacuum of less than l mm. Hg, e.g. 0.001 mm. although a vacuum of up to about 4.5 rnm. can be used.
  • the desiccation product is then disintegrated to provide granules having a high specific surface area.
  • the particles generally are from l0 mesh to 200 mesh, preferably 40 to 100 mesh (U.S. Standard Sieve).
  • a concentrated electrolyte can be put into the polymer, e.g. sodium chloride or ammonium bicarbonate, to pull the water out.
  • the freeze drying or concentrated electrolyte procedure is employed to avoid shrinkage of the polymer to the non-porous type as it dries.
  • the porous product or sponge can be prepared by polymerizing the acrylate or methacrylate in the presence of a blowing agent which will decompose at the temperature of polymerization.
  • the blo-wing agent procedure can be used whether the polymerization is carried out without a solvent 0r whether water is employed.
  • the porous polymer is formed with the aid of a blowing agent preferably 0.5 to 5% of blowing agent is used based on the Weight of the polymerizable monomer although up to of foaming agent can be used.
  • the foamed polymer can be extruded to produce rods of a predetermined diameter as a filter of the foam can be disintegrated into granules as set forth above.
  • the tobacco filter of the present invention can be employed in cigarettes, cigars, pipes or other smoking implements.
  • the filter can be the sole filter or other filters can be employed such as activated carbon, plasticized cellulose acetate fibers, corrugated paper, polyethylene particles or fibers, etc.
  • the filtering elements of the present invention are also useful as non-migratory humectant carriers when presaturated with a polyhydric alcohol, e.g. glycerine, propylene glycol, ethylene glycol, polypropylene glycol, sorbitol, mannitol, corn syrup.
  • a polyhydric alcohol e.g. glycerine, propylene glycol, ethylene glycol, polypropylene glycol, sorbitol, mannitol, corn syrup.
  • a polyhydric alcohol e.g. glycerine, propylene glycol, ethylene glycol, polypropylene glycol, sorbitol, mannitol, corn syrup.
  • a polyhydric alcohol e.g. glycerine, propylene glycol, ethylene glycol, polypropylene glycol, sorbitol, mannitol, corn syrup.
  • the hydrophilic polymer filtering element can be impregnated with a flavor, e.g. menthol, peppermint, or natural or artificial tobacco flavor for slow release of the flavor imparting compound to the smoke.
  • a flavor e.g. menthol, peppermint, or natural or artificial tobacco flavor for slow release of the flavor imparting compound to the smoke.
  • blowing or foaming agents examples include sodium bicarbonate, sodium bicarbonate-citric acid (e.g. 4:3), potassium bicarbonate, azobisisobutyronitrile, N,N dimethyl N,N' dinitrosoterephthalamide, p,p' oxybis (benzenesulfonyl hydrazide), urea-biuret (1:2), diazoaminobenzene, 1,6-di-n-decyl azobisformamide, diphenyl 4,4'di(sulfonylazide) p,p'oxybis (N-nitroso N methyl benzenesulfonamide), tetramethylene dinitroso dimethyl urethane, benzene sulfonic acid hydrazide, -naphthalene sulfonic acid hydrazide, diphenyl sulfone-3,3'disulfonyl hydrazide, benz
  • the hydrophilic monomer employed is preferably a hydroxy lower alkyl acrylate or methacrylate or a hydroxy lower alkoxy lower alkyl acrylate or methacrylate, e.g. 2hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, diethylene glycol monomethacrylate, diethylene glycol monoacrylate, 2hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, 3-hydroxypropyl acrylate, 3-hydroxypropyl methacrylate, dipropylene glycol monomethacrylate.
  • Acrylamide, methylol acrylamide, methacrylamide, methylol methacrylamide and diacetone acrylamide are useful but less preferred hydrophilic monomers.
  • the most preferred monomer is 2-hydroxyethyl methacrylate and the next most preferred monomer is 2-hydroxyethyl acrylate.
  • hydroxyalkyl mono acrylates and methacrylates a small amount of the diacrylate or dimethacrylate is also formed. Ordinarily this need not be removed since it aids in forming cross linked hydrophilic polymers.
  • the preferred polymers of the invention are cross linked although uncross linked hydrophilic acrylates and methacrylates can also be employed.
  • cross linking agent When cross linked polymers are prepared the cross linking agent can be present in an amount of 0.05 to of the total monomers, usually not over 10% and preferably not over 2%. The most preferred range of cross linking agent is 0.1 to 0.2% of the total monomers.
  • Typical examples of cross linking agents include ethylene glycol diacrylate, ethylene glycol dimethacrylate, 1,2-butylene dimethacrylate, 1,3-butylene dimethacrylate, 1,4-butylene dimethacrylate, propylene ⁇ glycol diacrylate, propylene glycol diacrylate, diethylene glycol dimethacrylate, dipropylene glycol dimethacrylate, diethylene glycol diacrylate, dipropylene glycol diacrylate, divinyl benzene, divinyl toluene, diallyl tartrate, allyl pyruvate, allyl malate, divinyl tartrate, triallyl melamine, N,N'methylene bis acrylamide, glycerine trim
  • diallyl ester of benzene phosphonic acid polyester maleic anhydride with triethylene glycol, polyallyl glucose, e.g. triallyl glucose, polyallyl sucrose, e.g. pentaallyl sucrose, sucrose diacrylate, glucose dimethacrylate, pentaerythritol tetraacrylate, sorbitol dimethacrylate, di allyl aconitate, divinyl citraconate, diallyl fumarate.
  • polyallyl glucose e.g. triallyl glucose
  • polyallyl sucrose e.g. pentaallyl sucrose, sucrose diacrylate, glucose dimethacrylate, pentaerythritol tetraacrylate, sorbitol dimethacrylate, di allyl aconitate, divinyl citraconate, diallyl fumarate.
  • partial esters of polybasic acids such as mono 2hydroxy propyl itaconate, mono 2-hydroxyethyl itaconate, mono 2- hydroxyethyl citraconate, mono-2-hydroxypropyl aconitate, mono 2-hydroxyethyl maleate, mono-2-hydroxypropyl fumarate, monomethyl itaconate, monoethyl itaconate, mono Methyl Cellosolve ester of itaconic acid (Methyl Cellosolve is the monomethyl ether of diethylene glycol), mono Methyl Cellosolve ester of maleic acid.
  • partial esters of polybasic acids such as mono 2hydroxy propyl itaconate, mono 2-hydroxyethyl itaconate, mono 2- hydroxyethyl citraconate, mono-2-hydroxypropyl aconitate, mono 2-hydroxyethyl maleate, mono-2-hydroxypropyl fumarate, monomethyl itaconate, monoethyl itaconate, mono Methyl Cell
  • catalysts for carrying out the polymerization there is employed free radical catalyst in the range of 0.05 to 1% of the polymerizable hydroxyalkyl ester, for example, the preferred amount of catalyst is 0.1 to 0.2% of the monomer.
  • Typical catalysts include t-butyl peroctoate, benzoyl peroxide, isopropyl percarbonate, methylethylketone peroxide, cumene hydroperoxide and dicumylperoxide.
  • Irradiation e.g., by ultra violet light or gamma rays, also can be employed to catalyze the lpolymerization. Polymerization can be done at 20 to 150 C., usually 40 to 90 C.
  • Typical examples of suitable cross linked hydrophilic polymers are those prepared in Wichterle Patent 2,976,- 576, Examples l, 2, 3 and 4 followed by freeze drying, e.g. at 10 C. in place of molding and the polymers prepared in Wichterle Patent 3,220,960, e.g. Examples III, V, VI, VII and IX with the modification that the polymers are freeze dried, e.g. at 5 C. to form porous products having large surface areas. While the formation of micro pores as in Wichterle Patent 2,976,576 Example 3 is adequate for liquid filtration it does not give a Satisfactory cigarette filter. Instead procedures such as those set forth supra must be resorted to.
  • FIGURE 1 is a perspective View of a cigarette having a lter according to the invention.
  • FIGURE 2 is a sectional view taken along the line 2&-2 0f FIGURE l
  • FIGURE 3 is a sectional view taken along the line 3 of FIGURE 2;
  • FIGURE 4 is a sectional view of a smoking pipe filter according to the invention.
  • a cigarette designated generically at 2 comprising tobacco 4, foamed, hydrophilic acrylate or methacrylate filter 6 and cellulose acetate fibers 8 encased in an overall outer paper wrapper 10.
  • the particles of -filter 6 have a mesh size of -40 to 100 mesh and a surface area of about 200 m.2/g.
  • FIGURE 4 shows a smoking pipe filter 12 containing foamed hydrophilic acrylate or methacrylate particles 14 encased in cartridge 16.
  • the cartridge has screens (not shown) at both ends, the openings in the screen are of smaller size, e.g. 325 mesh, than the particles of the highly porous acrylate or methacrylate, -40 to 100 mesh.
  • Example 1 100 grams of Z-hydroxyethyl methacrylate were mixed with 0.15 gram of tertiary butyl peroctoate. 0.2 gram of ethylene glycol dimethacrylate was added along with 1 gram of sodium bicarbonate. The mixture was heated to 70 C. and the resulting polymer was disintegrated into pellet size particles (30 mesh) by grinding and shearing. The pellets had 60% void space therein. The pellets were employed as a tobacco smoke filter in a cigarette.
  • ExampleZ The procedure of Example 1 was repeated but the pellets were mixed in a 50-50 mixture of glycerine and water for 8 hours to provide a non-migratory humectant action and dried. The resulting pellets were employed as a tobacco smoke filter in a cigarette.
  • Example 3 The process of Example 2 was repeated with the exception that tobacco avor was added to the glycerinewater mixture to impart a tobacco avor to the filtered smoke to replace the avor lost by filtration of the tars and other combustion products which normally impart the tobacco avor upon inhalation.
  • Example 4 In another embodiment a alcoholic solution of menthol based on the hydrophilic polymer was employed as a flavoring agent along with the tobacco flavor in Example 3.
  • the alcoholic solutions may be employed so as to result in an amount ranging from 1 to 90% by weight of the hydrophilic polymer.
  • the alcoholic solution normally is saturated with menthol.
  • the 10% alcoholic solution is preferred, particularly if glycerine is employed as the humectant.
  • Example 5 90 grams of 2-hydroxyethyl methacrylate, 10 grams of itaconic acid, 2 grams of t-butyl peroctoate, 1.5 grams of sodium bicarbonate were heated to 85 C. for 6 hours and the resulting porous, foamed, polymer used as a cigarette filter.
  • Example 6 A solution was prepared consisting of 30 grams of 2- hydroxyethyl mehtacrylate, 0.3 gram of ethylene glycol dimethacrylate, 0.15 gram of ammonium persulfate, 0.1 gram of sodium bisulfite and 70 grams of water. The solution was then poured into a 200 ml. beaker and placed in a closed chamber at a temperature of 50 C. under a carbon dioxide atmosphere. Polymerization occurred Within 30 minutes to form a white, opaque, spongy, cylindrical mass. (The polymer precipitates as a foam.) This mass was frozen at 5 C. and subjected to a vacuum of 1 mm. Hg absolute to remove the water from the solid phase.
  • the dried, rigid, friable mass was then crushed to provide granules having a high specific surface area, i.e. 50 HL2/g., a pore volume of 70% and a particle size of l-40 mesh to 100 mesh.
  • the product was employed as a cigarette iilter.
  • Example 7 The procedure of Example 6 was repeated omitting the ethylene glycol dimethacrylate to produce an uncross linked hydrophilic polymer which also was useful as a cigarette filter.
  • Example 8 pire volume of 80% and was employed as a cigarette fi ter.
  • Example 9 Granules prepared in accordance with Example 6 were screened to provide a fraction with a 40 mesh particle size.
  • Cigarette filters were prepared by removing one half of the cellulose filter of a conventional cigarette and filling the void with the prepared granules. Cigarettes prepared in this Ymanner were compared with control cigarettes of conventional construction.
  • the cigarettes were conditioned for 24 hours at 75 F. and 60% relative humidity. Smoking was done in a room conditioned to 75i2 F. and 60i2% R.H.
  • the smoking system consisted of the cigarette, a tared Cambridge iilter assembly and a smoking machine that produces a 35 ml. puf of 2-second duration at a rate of one puff per minute. All cigarettes were smoked to the predetermined butt length of 33 mm. Five cigarettes were smoked through each Cambridge filter and the results calculated and reported in terms of one cigarette.
  • Moisture was determined by GLC. This determination was made according to the procedure described in a paper entitled Determination of Moisture in Total Particulate Matter by Schultz and Spears in Tobacco Science, vol. X, pp. 75-76 (1966).
  • the filter assembly As soon as the filter assembly had been weighed, it was opened and the filter placed in a dry 30 ml. serum bottle. The inner face of the filter holder was then wiped with one-fourth of a Cambridge filter pad and this added to the serum bottle. Ten ml. of dry dioxane-isopropanol (100:1) was measured from an automatic burette into the serum bottle and the stopper inserted. The bottle was shaken for 20 minutes on a Wrist-Action shaker.
  • a sample of 10 microliters was Withdrawn with a Hamilton syringe through the rubber serum cap and subjected to gas chromatography in an Aerograph -P3 gas chromatograph.
  • the moisture content of the particulate matter was read from a calibration curve made by adding known amounts of Water to the solvent mixture. Filters conditioned at 75 F. and 60% R.H. were run and the average value of the moisture content subtracted from the amounts found in the used filters to get the net moisture content.
  • the lter element of the present invention is eiective in removing tar and nicotine from tobacco smoke.
  • Example 10 The procedure of Example 6 was repeated but there was included in the aqueous mixture 0.4 gram of sodium bicarbonate and 0.3 gram of citric acid to aid in forming the foamed product.
  • a tobacco smoke iilter comprising a substantially cylindrical charge of a hydrophilic particulate polymeric compound, said particulate lter material being highly porous and having a high surface area and being selected from the group consisting of polymers of hydroxy lower alkyl acrylates, hydroxy lower alkyl methacrylates, hydroxy lower alkoxy lower alkyl acrylates and hydroxy lower alkoxy lower alkyl methacrylates, wherein the highly porous, high surface area characteristics are produced by foaming or freeze drying the polymer mix.
  • acrylate or methacrylate comprises a polymer of a member of the group consisting of hydroxyethyl acrylate, hydroxyethyl methacrylate, hydroxypropyl acrylate and hydroxypropyl methacrylate.
  • a cigarette according to claim 6 wherein the polymer is a polymer of Z-hydroxyethyl methacrylate.
  • porous hydrophilic acrylate or methacrylate polymer is produced by polymerizing said acrylate or methacrylate in an aqueous medium to produce a solid polymer, then freezing the polymer below 0 C. and subjecting the frozen polymer to a vacuum to dry the polymer and thereby form the pores.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Cigarettes, Filters, And Manufacturing Of Filters (AREA)
US756128A 1968-08-29 1968-08-29 Tobacco smoke filters Expired - Lifetime US3470883A (en)

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JP (1) JPS4916639B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
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Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3567118A (en) * 1968-09-05 1971-03-02 Nat Patent Dev Corp Entrapped essences in dry composite fiber base products giving a strong fragrance when wet in water
US3608564A (en) * 1968-05-15 1971-09-28 Mitsubishi Rayon Co Cigarette filter
US3655129A (en) * 1968-07-17 1972-04-11 Ppg Industries Inc Slow release films and methods of making same
US3660115A (en) * 1969-05-09 1972-05-02 Fries & Fries Inc Solid particulate aromatic materials and process for preparing same
DE2159352A1 (de) * 1970-12-09 1972-06-29 Engel W Vorgefertigter Gegenstand aus Kunstharz
US3882877A (en) * 1972-04-26 1975-05-13 Rothmans Of Pall Mall Filter for tobacco smoke
US3939260A (en) * 1969-11-26 1976-02-17 Societe Anonyme Dite: Orsymonde Therapeutic and cosmetic compositions
US20070181141A1 (en) * 2005-12-13 2007-08-09 Philip Morris Usa Inc. Smoking articles with activated carbon and sodium bicarbonate-treated fibers and method of treating mainstream smoke
US20090133704A1 (en) * 2003-11-07 2009-05-28 Strickland James A Tobacco Compositions
US20110297166A1 (en) * 2009-02-23 2011-12-08 Manabu Takeuchi Non-heating tobacco flavor suction device
US20120024306A1 (en) * 2010-03-26 2012-02-02 Philip Morris Usa Inc. Biopolymer foams as filters for smoking articles
CN102740946A (zh) * 2009-03-16 2012-10-17 原生生物国际股份公司 向冷性水凝胶及其作为过滤器的用途
US8627828B2 (en) 2003-11-07 2014-01-14 U.S. Smokeless Tobacco Company Llc Tobacco compositions
US9089162B2 (en) 2010-03-26 2015-07-28 Philip Morris Usa Inc. Smoking articles containing polymers of polycarboxylic acid esters
CN104910568A (zh) * 2015-01-28 2015-09-16 云南中烟工业有限责任公司 一种石墨烯-聚合物复合气凝胶的滤嘴香料棒及其制备方法
CN105661638A (zh) * 2016-01-26 2016-06-15 广东中烟工业有限责任公司 一种提高卷烟烟气中水分含量的方法
US20170065000A1 (en) * 2014-05-20 2017-03-09 Rai Strategic Holdings, Inc. Electrically-powered aerosol delivery system
US20190154414A1 (en) * 2016-11-01 2019-05-23 Midwest Outdoor Holdings, LLC Ballistic barrel cleaning shell
US11112223B2 (en) * 2020-01-24 2021-09-07 Midwest Outdoor Holdings, LLC Bore cleaning device operable to clean a bore of a firearm

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JPS5310050U (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * 1976-04-23 1978-01-27
RU2292824C2 (ru) 2002-09-19 2007-02-10 Джапан Тобакко Инк. Сигаретный фильтр
GB2395650B (en) * 2002-11-27 2005-09-07 Filtrona Int Ltd Tobacco smoke filter
US20050061338A1 (en) * 2003-06-18 2005-03-24 Olegario Raquel M. Reduction of polycyclic aromatic hydrocarbons in tobacco smoke using palladium salts
GB201817568D0 (en) * 2018-10-29 2018-12-12 Nerudia Ltd Smoking substitute consumable
GB201817569D0 (en) * 2018-10-29 2018-12-12 Nerudia Ltd Smoking substitute consumable
KR102386081B1 (ko) * 2020-04-22 2022-04-12 주식회사 케이티앤지 흡연 물품용 필터 및 이를 포함하는 흡연 물품
CN112237787B (zh) * 2020-10-23 2022-04-01 马鞍山中经悦怿生命科技有限公司 过滤颗粒的生产设备及方法

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US2739598A (en) * 1953-05-04 1956-03-27 R S Aries And Associates Inc Filter for tobacco smoke
US2933460A (en) * 1956-05-29 1960-04-19 Rohm & Haas Ion-exchange fibers, films and the like from sulfur containing alkoxymethyl monomers
US3366582A (en) * 1964-04-28 1968-01-30 American Can Co Cellulosic copolymer filter material

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US2739598A (en) * 1953-05-04 1956-03-27 R S Aries And Associates Inc Filter for tobacco smoke
US2933460A (en) * 1956-05-29 1960-04-19 Rohm & Haas Ion-exchange fibers, films and the like from sulfur containing alkoxymethyl monomers
US3366582A (en) * 1964-04-28 1968-01-30 American Can Co Cellulosic copolymer filter material

Cited By (33)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3608564A (en) * 1968-05-15 1971-09-28 Mitsubishi Rayon Co Cigarette filter
US3655129A (en) * 1968-07-17 1972-04-11 Ppg Industries Inc Slow release films and methods of making same
US3567118A (en) * 1968-09-05 1971-03-02 Nat Patent Dev Corp Entrapped essences in dry composite fiber base products giving a strong fragrance when wet in water
US3660115A (en) * 1969-05-09 1972-05-02 Fries & Fries Inc Solid particulate aromatic materials and process for preparing same
US3939260A (en) * 1969-11-26 1976-02-17 Societe Anonyme Dite: Orsymonde Therapeutic and cosmetic compositions
DE2159352A1 (de) * 1970-12-09 1972-06-29 Engel W Vorgefertigter Gegenstand aus Kunstharz
US3688985A (en) * 1970-12-09 1972-09-05 Walter H Engel Plastic article of manufacture impregnated with volatile matter
US3882877A (en) * 1972-04-26 1975-05-13 Rothmans Of Pall Mall Filter for tobacco smoke
US8636011B2 (en) 2003-11-07 2014-01-28 U.S. Smokeless Tobacco Company Llc Tobacco compositions
US20090133704A1 (en) * 2003-11-07 2009-05-28 Strickland James A Tobacco Compositions
US10945454B2 (en) 2003-11-07 2021-03-16 U.S. Smokeless Tobacco Company Llc Tobacco compositions
US8469036B2 (en) 2003-11-07 2013-06-25 U.S. Smokeless Tobacco Company Llc Tobacco compositions
US8627828B2 (en) 2003-11-07 2014-01-14 U.S. Smokeless Tobacco Company Llc Tobacco compositions
US10765140B2 (en) * 2003-11-07 2020-09-08 U.S. Smokeless Tobacco Company Llc Tobacco compositions
US10098376B2 (en) 2003-11-07 2018-10-16 U.S. Smokeless Tobacco Company Llc Tobacco compositions
US9491971B2 (en) * 2005-12-13 2016-11-15 Philip Morris Usa Inc. Specifically-defined smoking article with activated carbon sorbent and sodium bicarbonate-treated fibers and method of treating mainstream smoke
US20070181141A1 (en) * 2005-12-13 2007-08-09 Philip Morris Usa Inc. Smoking articles with activated carbon and sodium bicarbonate-treated fibers and method of treating mainstream smoke
US20170042220A1 (en) * 2005-12-13 2017-02-16 Philip Morris Usa Inc. Method of Manufacturing Smoking Article With Activated Carbon Sorbent and Sodium Bicarbonate-Treated Fibers
US20110297166A1 (en) * 2009-02-23 2011-12-08 Manabu Takeuchi Non-heating tobacco flavor suction device
US9138550B2 (en) * 2009-02-23 2015-09-22 Japan Tobacco Inc. Non-heating tobacco flavor suction device
CN102740946A (zh) * 2009-03-16 2012-10-17 原生生物国际股份公司 向冷性水凝胶及其作为过滤器的用途
US9089162B2 (en) 2010-03-26 2015-07-28 Philip Morris Usa Inc. Smoking articles containing polymers of polycarboxylic acid esters
US10039310B2 (en) 2010-03-26 2018-08-07 Philip Morris Usa Inc. Smoking articles containing polymers of polycarboxylic acid esters
US9226524B2 (en) * 2010-03-26 2016-01-05 Philip Morris Usa Inc. Biopolymer foams as filters for smoking articles
US10264815B2 (en) 2010-03-26 2019-04-23 Philip Morris Usa Inc. Biopolymer foams as filters for smoking articles
US20120024306A1 (en) * 2010-03-26 2012-02-02 Philip Morris Usa Inc. Biopolymer foams as filters for smoking articles
US20170065000A1 (en) * 2014-05-20 2017-03-09 Rai Strategic Holdings, Inc. Electrically-powered aerosol delivery system
CN104910568A (zh) * 2015-01-28 2015-09-16 云南中烟工业有限责任公司 一种石墨烯-聚合物复合气凝胶的滤嘴香料棒及其制备方法
CN105661638A (zh) * 2016-01-26 2016-06-15 广东中烟工业有限责任公司 一种提高卷烟烟气中水分含量的方法
CN105661638B (zh) * 2016-01-26 2019-08-30 广东中烟工业有限责任公司 一种提高卷烟烟气中水分含量的方法
US20190154414A1 (en) * 2016-11-01 2019-05-23 Midwest Outdoor Holdings, LLC Ballistic barrel cleaning shell
US10578408B2 (en) * 2016-11-01 2020-03-03 Midwest Outdoor Holdings, LLC Ballistic barrel cleaning shell
US11112223B2 (en) * 2020-01-24 2021-09-07 Midwest Outdoor Holdings, LLC Bore cleaning device operable to clean a bore of a firearm

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GB1255564A (en) 1971-12-01

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