US3608564A - Cigarette filter - Google Patents
Cigarette filter Download PDFInfo
- Publication number
- US3608564A US3608564A US825069A US3608564DA US3608564A US 3608564 A US3608564 A US 3608564A US 825069 A US825069 A US 825069A US 3608564D A US3608564D A US 3608564DA US 3608564 A US3608564 A US 3608564A
- Authority
- US
- United States
- Prior art keywords
- cigarette filters
- fibers
- cigarette
- finely divided
- percent
- 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
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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
- A24D3/08—Use of materials for tobacco smoke filters of organic materials as carrier or major constituent
Definitions
- Cigarette filters comprising one graft polymer selected from the group consisting of polyvinyl alcohol grafted with at least one monoethylenically unsaturated vinyl BACKGROUND OF THE INVENTION 1.
- This invention relates to a cigarette filter which effectively removes tar and nicotine, and to a method of making the same.
- cellulose derivatives such as cellulose, methyl cellulose, oxycellulose and partially hydrolyzed cellulose
- vinyl polymers such as, polymethyl methacrylate, polyvinyl acetate and polyvinyl butyral, activated alumina, silica gel, ion exchange resins and activated carbon as the adsorbent.
- This invention has been completed as the result of many studies about methods for producing a cigarette filter having good tar and nicotine removal which does not injure the flavor of the cigarette atsmoking.
- the present invention involves the discovery of an improved cigarette filter formed from at least one graft copolymer selected from the group consisting of polyvinyl alcohol grafted with at least one monoethylenically unsaturated vinyl monomer and partially saponified polyvinyl acetate grafted with at least one monoethylenically unsaturated vinyl monomer.
- This invention relates to a cigarette filter which is saponified by comprising a graft copolymer composed of polyvinyl alcohol grafted with a copolymerizable vinyl compound and partially saponified polyvinyl acetate grafted with copolymerizable vinyl compound.
- the most preferable filter in this invention is one comprising a porous finely divided powder of said graft copolymer having a surface area of 15 to 200 m. /g. and a 10 to 300 mesh particle size dispersed in a bundle of mechanically crimped cellulose diacetate fibers having a 1.6 to 15 denier monofilaacrylamide, acrylonitrile, vinyl chloride, vinylidene chloride, vinyl acetate, ethylene, propylene and styrene. These monomers are used alone or by mixing two or more thereof. Ester-type monomers are most preferred among these monomers, and graft polymers produced therefrom have high affinity for tar and nicotine. Consequently, good filters are obtainable.
- the amount of the vinyl monomer grafted to the base polymer is from 10 to 310 weight percent to the polymer. If it is less than 10 weight percent, effective results are not obtained in the resulting graft polymer, and if it is over 310 weight percent, the flavor of the smoke decreases. Further, it is not preferred to graft in an amount of over 310 weight percent because of difficulty in processing.
- the amount of the branching polymer is preferably from 10 to 310 weight percent to the base polymer. 1
- graft polymers in this range have excellent affinity for tar and nicotine and give excellent flavor at smoking, it is possible to produce excellent cigarette filters using said polymers.
- any method may be adopted according to the kinds of vinyl monomers, such as a method using a persulfate, a peroxide, a cerium salt or an azobisisobutylonitrile as the catalyst, or methods utilizing radioactive rays, etc.
- the polymerization may be carried out either in a homogenous system or in a heterogeneous system. In other words, the polymerization process per se is not critical.
- the finely divided powder has a 10 to 300 mesh, preferably from 60 to mesh, particle size, and most preferably a 15 to 200 m. /g. surface area. It becomes a porous finely divided powder.
- the specific gravity thereof is from 1.1 to 0.2.
- the finely divided powder can be produced by the following methods.
- a polymer slurry which is prepared as a solution or dispersion of graft polymer gelatinized in poor solvent, water or by salting out gradually, is separated by precipitation, dried, powderedand screened to arrange the particle size within the range described above.
- a solution or dispersion containing the graft polymer is frozen at less than 20 C., and then solvent is removed under a reduced pressure of from 18 mm. Hg to 1.2Xl0 mm. Hg After drying, the polymer is powdered.
- a solution or dispersion containing the graft polymer is dried by spraying into a dry heating stream at 60- 130 C. or by spraying at from 40 to C. under from 260 to 58 mm. Hg., and then the polymer is powdered.
- the resulting porous finely divided powder is dispersed in a raw material of the filter, for example, an opened fiber bundle, and then the fiber bundle is formed into a rod shape and finally into the filter tip shape.
- the method for producing the filter by adding the powder into the fiber bundle is not restricted.
- the easiest method comprises uniformly dispersing the powder in an opened tow by a disperser as used in the step of making common filter plugs, such as by rolling up a paper to a 7.9 mm. diameter with a cigarette paper rolling machine I to produce a filter plug, and cutting such a plug to a 17 mm.
- the most preferred filter in this invention is that comprising from 5 to 80 percent of a porous finely divided powder (consisting of the graft polymer as described above based on the weight of fibers) dispersed in a fiber bundle of mechanically crimped cellulose diacetate having a 1.6 to 8 denier monofilament size, a 30,000 to 90,000 total filament denier, and with crimps offrom 5 to 30/inch.
- the finely divided powder of the graft polymer prepared by grafting the monoethylenically unsaturated vinyl monomers to the polyvinyl alcohol and the partially saponified polyvinyl acetate does not have a large adsorbing capacity for water, and is comparatively hard before smoking. Further, it does not become sodden by moisture in the mouth or the tobacco and have the adsorption resistance increase by dissolution of polyvinyl alcohol by the moisture. Furthermore, since the finely divided powder has a suitable hydrophobic property, it has the characteristic that the smoke of the tobacco does not dry excessively. Moreover, since the removal of perfume, often added during preparation of the tobacco, is small when compared with the removal upon the use of polyvinyl alcohol, the smoking taste of the tobacco is not injured.
- an adhesive consisting of a solution or dispersion containing more than weight percent of a plasticizer such as triacetin, the acetate of ethyleneglycol, the acetate of. polyethylene glycol and methylethyl ether, etc., or vinyl acetate, may be sprayed in an amount of from 5 to 18 weight percent (to the fiber tow) in order to bind the fibers to themselves, as well as to bind the finely divided powder and fibers. If desired, other additives or adsorbents for injurious materials may be used together therewith.
- a plasticizer such as triacetin, the acetate of ethyleneglycol, the acetate of. polyethylene glycol and methylethyl ether, etc., or vinyl acetate
- any fiber for example polypropylene fiber or viscose fiber, which is known as suitable for cigarette filter fibers, may be used.
- a filter which is produced by spraying a solution or dispersion of the graft polymer onto the filter tow to cause the graft polymer to adhere to the surface of fibers, removing solvent and forming said tow by rolling it up with a paper is included in this invention.
- filters in which a finely divided powder is contained as associated matter are included in this invention.
- filters in which a finely divided powder is contained therein as capsules are included in this invention.
- filter tips in which a finely divided powder is contained therein as capsules are included in this invention.
- filter tips in which said powder is sandwiched between fiber filters are included in this invention.
- a polymer prepared by grafting methyl methacrylate to polyvinyl alcohol and partially saponified polyvinyl acetate is quite soluble in acetone, dimethylsulfoxide (DMSO) and dimethylformamide (DMF).
- DMSO and DMF are not suitable as the solvent of the graft polymer, and acetone is preferably used.
- Solvents for polymers grafted by vinyl monomers besides methyl methacrylate are as follows.
- Methyl acrylate Ethyl acetate, DMSO and DMF.
- Ethyl acrylate Toluene, DMSO and DMF.
- Butyl acrylute Toluene, DMSO and DMF.
- Acrylamide DMF.
- Smoking device definite flux type Gas permeation resistance Conditions ofsmoking Smokingtime: 2 sec/round Smoking interval: 58 sec Smoking flux: 17.5 ml/sec Smoking round: 8/cigarette Method for collecting smoke:
- the tobacco used for determination was conditioned at 25 C., and 60 percent RH for over 48 hours.
- EXAMPLE l 100 parts of partially saponified polyvinyl alcohol having an 8,000 average degree of polymerization and a 92 percent saponification value was dissolved completely in 1,600 parts of boiled distilled water at 85 C. in a nitrogen stream, and then 2.5 parts of the cerium salt of ammonium sulfate, 230 parts of methyl methacrylate, and 2.0 parts of conc. nitric acid (concentration 60-62 percent) were added thereto. The graft polymerization took place at 60 C. for 4 hours (degree of grafting was weight percent). After the reaction was over, the polymerization solution was gradually poured into about a 10-fold amount of methanol with vigorous stirring. The resulting precipitate was washed, filtered and dried, and then powdered to give a finely divided powder having a 60-80 mesh particle size. This powder had a 14.2 m. /g. surface area average.
- a tow of cellulose diacetate filaments mechanically crimped having a 4 denier monofilament size and a 55,000 total filament denier was opened.
- the finely divided powder described above consisting of polyvinyl alcohol grafted with methyl methacrylate
- a gas stream at from 28 to 30 cm./sec. flux.
- the tow was then rolled up to a 7.9 mm. diameter using a paper by means of a cigarette plug making machine to produce a filter plug.
- the plug was cut to a 17 mm. length to produce tips.
- a tip was then put onto an end of the standard cigarette by a cellophane tape having a 12 mm. width so as to keep it in close contact with the cutting surface.
- the properties of the resulting filter are shown in table 1, in comparison with those of a filter which does not contain a finely divided graft polymer powder.
- the filter of this invention not only provides good removal of tar and nicotine in tobacco smoke, but good removal of phenolic compounds (stimulative ingredient) and gives an excellent smoking flavor to smokers.
- a tow of cellulose diacetate filaments mechanically crimped having 4 denier monofilaments and a 55,000 total filaments denier was opened. After spraying triacetin in an amount of 6.7 percent based on the weight of the tow, the finely divided powder described above was dispersed in the amount of 32.5 weight percent onto the tow by an electromagnetic vibrator. The tow was then rolled upon a cigarette plug making machine and sufficiently dried. After being plasticized, a plug having a 7.9 mm. diameter was obtained.
- the resulting plug was cut into a 17 mm. length to produce tips.
- a tip having a definite gas-permeation resistance By selecting a tip having a definite gas-permeation resistance, the characteristics of the filter were determined. The results are shown in table 2.
- the reaction product was force-sprayed into a heating stream at 128 C. to form a finely divided powder. From this finely divided powder, particles of a 60 to 90 mesh size were selected. The surface area of the resulting finely divided powder was approximately 28 m. /g,, measured by the B.E.T. method.
- a tow of mechanically crimped polypropylene filaments having a 9.5 denier monofilament and an 82,000 denier total filament size was sufficiently opened.
- the finely divided powder of the graft copolymer described above was dispersed in the amount of 28 weight percent, to the tow.
- the tow containing the finely divided powder was treated by a cigarette plug making machine to produce a filter plug having a 7.9 mm. diameter, which was then cut to 102:0.2 mm. By further cutting, filter tips having a 17 mm. length were obtained.
- a graft polymer was produced by mixing 100 parts of partially saponified polyvinyl alcohol which had a 1,750 average degree of polymerization and an percent saponification value, 30 parts of methyl methacrylate and 150 parts of methacrylonitrile in water, and then carrying out emulsion polymerization. Into the system containing the polymer solu tion was added parts of activated clay. The mixture was frozen at 63C. and dried under 1 mm. Hg.
- the graft polymer obtained was powdered into 60 to 80 mesh size by a mill.
- the finely divided powder had a 92 mF/g. surface area.
- a tow consisting of mechanically crimped polypropylene filaments having a 9.5 denier monofilament size and an 80,000 total filament size was opened by compressed air. Then a toluene solution of 4.2 weight percent (to the tow) of ethylene-vinyl acetate copolymer (72:28) was sprayed onto the tow. Then the finely divided powder described above was added to the tow in an amount of 3l.l weight percent by a disperser. The tow containing the finely divided powder was treated by a cigarette plug making machine to produce a filter plug having a 7.9 mm. diameter, which was then cut to 1021202 mm. By further cutting, filter tips having a 17 mm. length were obtained.
- the graft polymer was dissolved in toluene to produce a solution having a 2 weight percent concentration.
- Mechanically crimped cellulose diacetate filaments having a 4 denier monofilament size and a 55,000 denier total filament size were sufficiently opened, and then the toluene solution containing the graft polymer was sprayed thereon by a centrifugal device for adding a plasticizer.
- the graft polymer was contained in the low at an amount of weight percent. Triacetin was then sprayed (6 weight percent) onto the tow by a centrifugal plasticizer applicator.
- the tow was treated by a cigarette plug making machine to produce a plug having a 7.8 mm. diameter, which was then cut to 10230.2 mm. After further cutting to 17 mm., filter tips were obtained.
- a cigarette filter comprising a plug made from a bundle of opened fibers, the improvement which comprises said fibers having dispersed thereon a porous, finely divided, substantially hydrophobic graft polymer selected from the group consisting of polyvinyl alcohol grafted with at least one monoethylenically unsaturated vinyl monomer and partially saponified polyvinyl alcohol grafted with at least one monoethylenically unsaturated vinyl monomer.
- Cigarette filters of claim 1 wherein said grafted polymer has a polymerization degree of from 300 to 10,000.
- Cigarette filters of claim 1 wherein at least one of said vinyl monomers is a compound selected from the group consisting of lower alkyl esters of acrylic acid and lower alkyl esters of methacrylic acid.
- Cigarette filters of claim 4 wherein said lower alkyl ester of acrylic acid is a compound selected from the group consisting of methyl acrylate, ethyl acrylate and butyl acrylate.
- Cigarette filters of claim 8 wherein said grafted polymer is a finely divided powder having a particle size of from about 60 to about mesh.
- Cigarette filters of claim 8 wherein said finely divided powder has a surface area of from about 15 to about 200 mF/g.
- Cigarette filters of claim 8 wherein the weight of said finely divided powder ranges from about 5 to about 80 percent based on the weight of said plug.
- Cigarette filters of claim 1 wherein said plug comprises a crimped fiber bundle having a monofilament size ranging from about 1.6 to about 15 denier and from about 30,000 to about 000 total filament denier.
- Cigarette filters of claim 1 wherein said plug comprises fibers treated with an adhesive consisting of a solution or dispersion containing more than 20 percent by weight of a plasticizer.
- Cigarette filters of claim 19 wherein said fibers are sprayed with said adhesive in an amount of from 5 to 18 percent by weight of said fibers.
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Cigarettes, Filters, And Manufacturing Of Filters (AREA)
- Automatic Cycles, And Cycles In General (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP3272868 | 1968-05-15 |
Publications (1)
Publication Number | Publication Date |
---|---|
US3608564A true US3608564A (en) | 1971-09-28 |
Family
ID=12366888
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US825069A Expired - Lifetime US3608564A (en) | 1968-05-15 | 1969-05-15 | Cigarette filter |
Country Status (3)
Country | Link |
---|---|
US (1) | US3608564A (ja) |
DE (1) | DE1924495A1 (ja) |
GB (1) | GB1234134A (ja) |
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3856025A (en) * | 1972-03-23 | 1974-12-24 | Showa Denko Kk | Tobacco filters |
US3977417A (en) * | 1973-03-23 | 1976-08-31 | Philip Morris Incorporated | Smoking article and process for filtering tobacco smoke employing a cross-linked organic oil filter material |
US4006749A (en) * | 1975-01-31 | 1977-02-08 | Consolidated Cigar Corporation | Removal of harmful components from tobacco smoke |
US4903714A (en) * | 1987-08-25 | 1990-02-27 | R. J. Reynolds Tobacco Company | Smoking article with improved mouthend piece |
US4961415A (en) * | 1987-01-16 | 1990-10-09 | Kimberly-Clark Corporation | Controlled draft and efficiency filter element for smoking articles |
US5439010A (en) * | 1993-01-06 | 1995-08-08 | Dexter Speciality Materials Ltd. | Fibrous bonded sheet material |
US5538019A (en) * | 1993-11-03 | 1996-07-23 | Schweitzer-Mauduit International, Inc. | Spunbond cigarette filter |
EP1156156A1 (en) * | 2000-05-19 | 2001-11-21 | Air Products And Chemicals, Inc. | High performance air and oil filters impregnated with a binder |
US6676806B1 (en) | 1998-08-14 | 2004-01-13 | Schweitzer-Mauduit International, Inc. | Process for increasing the wet strength of porous plug wraps for use in smoking articles |
US20090038632A1 (en) * | 2005-03-29 | 2009-02-12 | Maria Cashmore | Porous Carbon Materials and Smoking Articles and Smoke Filters Therefor Incorporating Such Materials |
WO2009080369A3 (en) * | 2007-12-20 | 2009-11-26 | Philip Morris Products S.A. | Hollow/porous fibers and applications thereof |
Citations (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2077298A (en) * | 1934-03-31 | 1937-04-13 | Eastman Kodak Co | Process for the extraction of halogen from fluids |
US2343091A (en) * | 1940-08-03 | 1944-02-29 | Du Pont | Treatment of textiles and composition useful therefor |
US2902420A (en) * | 1955-02-18 | 1959-09-01 | Distillers Co Yeast Ltd | Graft copolymers |
US2933460A (en) * | 1956-05-29 | 1960-04-19 | Rohm & Haas | Ion-exchange fibers, films and the like from sulfur containing alkoxymethyl monomers |
US3004851A (en) * | 1957-12-02 | 1961-10-17 | Jones Graphic Products Of Ohio | Light sensitized coating compositions and the production thereof |
US3083172A (en) * | 1959-02-26 | 1963-03-26 | Rohm & Haas | Graft copolymer of an acrylic ester with poly(vinyl acetate) |
US3098838A (en) * | 1959-12-22 | 1963-07-23 | Nat Starch Chem Corp | Polyvinyl ethyl ether-vinyl acetate graft copolymers |
US3148101A (en) * | 1958-06-26 | 1964-09-08 | Celanese Corp | Process for making non-woven batt |
US3220960A (en) * | 1960-12-21 | 1965-11-30 | Wichterle Otto | Cross-linked hydrophilic polymers and articles made therefrom |
US3297786A (en) * | 1961-10-03 | 1967-01-10 | Yardney International Corp | Method of graft polymerizing onto hydrophobic substrates |
US3464423A (en) * | 1968-10-25 | 1969-09-02 | Stauffer Chemical Co | Tobacco smoke filter |
US3470883A (en) * | 1968-08-29 | 1969-10-07 | Nat Patent Dev Corp | Tobacco smoke filters |
-
1969
- 1969-05-13 DE DE19691924495 patent/DE1924495A1/de active Pending
- 1969-05-13 GB GB1234134D patent/GB1234134A/en not_active Expired
- 1969-05-15 US US825069A patent/US3608564A/en not_active Expired - Lifetime
Patent Citations (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2077298A (en) * | 1934-03-31 | 1937-04-13 | Eastman Kodak Co | Process for the extraction of halogen from fluids |
US2343091A (en) * | 1940-08-03 | 1944-02-29 | Du Pont | Treatment of textiles and composition useful therefor |
US2902420A (en) * | 1955-02-18 | 1959-09-01 | Distillers Co Yeast Ltd | Graft copolymers |
US2933460A (en) * | 1956-05-29 | 1960-04-19 | Rohm & Haas | Ion-exchange fibers, films and the like from sulfur containing alkoxymethyl monomers |
US3004851A (en) * | 1957-12-02 | 1961-10-17 | Jones Graphic Products Of Ohio | Light sensitized coating compositions and the production thereof |
US3148101A (en) * | 1958-06-26 | 1964-09-08 | Celanese Corp | Process for making non-woven batt |
US3083172A (en) * | 1959-02-26 | 1963-03-26 | Rohm & Haas | Graft copolymer of an acrylic ester with poly(vinyl acetate) |
US3098838A (en) * | 1959-12-22 | 1963-07-23 | Nat Starch Chem Corp | Polyvinyl ethyl ether-vinyl acetate graft copolymers |
US3220960A (en) * | 1960-12-21 | 1965-11-30 | Wichterle Otto | Cross-linked hydrophilic polymers and articles made therefrom |
US3297786A (en) * | 1961-10-03 | 1967-01-10 | Yardney International Corp | Method of graft polymerizing onto hydrophobic substrates |
US3470883A (en) * | 1968-08-29 | 1969-10-07 | Nat Patent Dev Corp | Tobacco smoke filters |
US3464423A (en) * | 1968-10-25 | 1969-09-02 | Stauffer Chemical Co | Tobacco smoke filter |
Non-Patent Citations (1)
Title |
---|
Irwin, T. Hydron New Miracle Plastic With Myriad of Uses Popular Science. Vol. 194, No. 2, February, 1969 p. 92 95. Pages 93 & 95 cited. * |
Cited By (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3856025A (en) * | 1972-03-23 | 1974-12-24 | Showa Denko Kk | Tobacco filters |
US3977417A (en) * | 1973-03-23 | 1976-08-31 | Philip Morris Incorporated | Smoking article and process for filtering tobacco smoke employing a cross-linked organic oil filter material |
US4006749A (en) * | 1975-01-31 | 1977-02-08 | Consolidated Cigar Corporation | Removal of harmful components from tobacco smoke |
US4961415A (en) * | 1987-01-16 | 1990-10-09 | Kimberly-Clark Corporation | Controlled draft and efficiency filter element for smoking articles |
US4903714A (en) * | 1987-08-25 | 1990-02-27 | R. J. Reynolds Tobacco Company | Smoking article with improved mouthend piece |
US5439010A (en) * | 1993-01-06 | 1995-08-08 | Dexter Speciality Materials Ltd. | Fibrous bonded sheet material |
US5538019A (en) * | 1993-11-03 | 1996-07-23 | Schweitzer-Mauduit International, Inc. | Spunbond cigarette filter |
US6676806B1 (en) | 1998-08-14 | 2004-01-13 | Schweitzer-Mauduit International, Inc. | Process for increasing the wet strength of porous plug wraps for use in smoking articles |
US6390305B1 (en) * | 2000-05-19 | 2002-05-21 | Air Products Polymers, L.P. | Saturant binder systems for high performance air and oil filters |
EP1156156A1 (en) * | 2000-05-19 | 2001-11-21 | Air Products And Chemicals, Inc. | High performance air and oil filters impregnated with a binder |
US20090038632A1 (en) * | 2005-03-29 | 2009-02-12 | Maria Cashmore | Porous Carbon Materials and Smoking Articles and Smoke Filters Therefor Incorporating Such Materials |
US9907336B2 (en) * | 2005-03-29 | 2018-03-06 | British American Tobacco (Investments) Limited | Porous carbon materials and smoking articles and smoke filters therefor incorporating such materials |
WO2009080369A3 (en) * | 2007-12-20 | 2009-11-26 | Philip Morris Products S.A. | Hollow/porous fibers and applications thereof |
US8453653B2 (en) | 2007-12-20 | 2013-06-04 | Philip Morris Usa Inc. | Hollow/porous fibers and applications thereof |
EA019459B1 (ru) * | 2007-12-20 | 2014-03-31 | Филип Моррис Продактс С.А. | Полые/пористые волокна, способ их получения и курительное изделие, включающее такие волокна |
CN101918488B (zh) * | 2007-12-20 | 2014-04-02 | 菲利普莫里斯生产公司 | 空心/多孔纤维及其应用 |
US9585422B2 (en) | 2007-12-20 | 2017-03-07 | Philip Morris Usa Inc. | Hollow/porous fibers and applications thereof |
Also Published As
Publication number | Publication date |
---|---|
GB1234134A (ja) | 1971-06-03 |
DE1924495A1 (de) | 1969-11-27 |
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