WO1996010929A1 - Cigarette filters and the like - Google Patents
Cigarette filters and the like Download PDFInfo
- Publication number
- WO1996010929A1 WO1996010929A1 PCT/IB1995/000853 IB9500853W WO9610929A1 WO 1996010929 A1 WO1996010929 A1 WO 1996010929A1 IB 9500853 W IB9500853 W IB 9500853W WO 9610929 A1 WO9610929 A1 WO 9610929A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- filter
- smoke
- filter according
- antioxidant
- sorbitol
- Prior art date
Links
- 235000019504 cigarettes Nutrition 0.000 title claims description 14
- 239000000779 smoke Substances 0.000 claims abstract description 21
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 10
- 239000003112 inhibitor Substances 0.000 claims abstract description 10
- 241000208125 Nicotiana Species 0.000 claims abstract description 9
- 235000002637 Nicotiana tabacum Nutrition 0.000 claims abstract description 9
- 230000003078 antioxidant effect Effects 0.000 claims abstract description 9
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims abstract description 8
- 239000000600 sorbitol Substances 0.000 claims abstract description 8
- BVCOHOSEBKQIQD-UHFFFAOYSA-N 2-tert-butyl-6-methoxyphenol Chemical compound COC1=CC=CC(C(C)(C)C)=C1O BVCOHOSEBKQIQD-UHFFFAOYSA-N 0.000 claims description 3
- YZNXOCVTNIERFC-UHFFFAOYSA-N 1-[2-(furan-2-yl)-5-hydroxy-6-(hydroxymethyl)-1,3-dioxan-4-yl]ethane-1,2-diol Chemical class O1C(CO)C(O)C(C(O)CO)OC1C1=CC=CO1 YZNXOCVTNIERFC-UHFFFAOYSA-N 0.000 claims description 2
- YBVRFTBNIZWMSK-UHFFFAOYSA-N 2,2-dimethyl-1-phenylpropan-1-ol Chemical compound CC(C)(C)C(O)C1=CC=CC=C1 YBVRFTBNIZWMSK-UHFFFAOYSA-N 0.000 claims description 2
- 239000002530 phenolic antioxidant Substances 0.000 claims description 2
- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 abstract description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 230000000711 cancerogenic effect Effects 0.000 description 4
- 230000000391 smoking effect Effects 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 231100000357 carcinogen Toxicity 0.000 description 2
- 231100000315 carcinogenic Toxicity 0.000 description 2
- 239000003183 carcinogenic agent Substances 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 229960002715 nicotine Drugs 0.000 description 2
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 2
- AXFBAIOSECPASO-UHFFFAOYSA-N pentacyclo[6.6.2.02,7.04,16.011,15]hexadeca-1(14),2(7),3,5,8(16),9,11(15),12-octaene Chemical compound C1=C(C=C23)C4=C5C3=CC=CC5=CC=C4C2=C1 AXFBAIOSECPASO-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 102000002004 Cytochrome P-450 Enzyme System Human genes 0.000 description 1
- 108010015742 Cytochrome P-450 Enzyme System Proteins 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000001917 fluorescence detection Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 231100000219 mutagenic Toxicity 0.000 description 1
- 230000003505 mutagenic effect Effects 0.000 description 1
- 238000002423 nitrogen--phosphorus detection Methods 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000013618 particulate matter Substances 0.000 description 1
- 231100000586 procarcinogen Toxicity 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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
- A24D3/14—Use of materials for tobacco smoke filters of organic materials as additive
Definitions
- the present invention is concerned with the treatment of filters for tobacco smoke particularly cigarette filters, to limit the carcinogenic effect of the smoke passed by them to the consumer
- One particular class of compounds falling within this category comprises the polycyclic aromatic hydrocarbons (PAH) which are converted by the cytochrome P450 enzyme system in the liver or the lung into oxygenated derivatives which have been shown to be carcinogenic
- PAH polycyclic aromatic hydrocarbons
- Pryor et al Science 220:425-427
- the effect of free-radicals in the smoke has been extensively discussed, for example by Church and Pryor Environ Hea lth Perspect 64111-126 (1985)
- GB-A-1044434 discloses the use of 2,4-monofurfuryl ⁇ dene sorbitol in cigarette filters to reduce the content of PAH in the smoke
- EP-B-0 345 362 discloses the use of a particular type of free-radical inhibitor in skin cosmetics
- the inhibitor in question is chosen from a group of furfurylidene derivatives of sorbitol. in particular 2.4-monofurfurylidene sorbitol and the tetra-O-alkyl derivatives thereof
- a method for preparing 2,4-monofurfuryl ⁇ dene sorbitol was disclosed in US-A-3.383.279 comprising gradual addition of furfurol to acidified sorbitol thus forming the 2,4-O-furfuryl ⁇ dene derivative
- a filter for tobacco smoke comprising means forming a passageway for smoke, characterised in that on a surface of the passageway arranged to contact the smoke there is provided an O-alkylated derivative of 2.4-monofurfuryl ⁇ dene sorbitol together with an antioxidant.
- the O-alkylated derivative is desirably a C 1-5 -alkyl derivative, e.g. the methyl derivative, and the tetra-O-alkyl derivative is preferred.
- the filter according to the invention is particularly represented by a cigarette filter, which may have any conventional construction arranged to provide a very large surface area in contact with the smoke passing through, for example packed filaments, open-cell foams, etc.
- the free-radical inhibitor may be incorporated in the filter at any effective level, but typically at 2.5-30 mg per filter, especially about 5-20 mg, particularly when tetra-0-methyl 2,4-monofurfuryl ⁇ dene sorbitol is used
- the filter also contains an antioxidant and the ratio by weight of the sorbitol derivative to the antioxidant is desirably from about 1.5:1 to 31, especially, about 2.1
- Particularly preferred antioxidants comprise phenolic antioxidants such as tert-butyl-hydroxyanisole (BHA) or tert-butyl-hydroxytoluene (BHT). It appears that there is synergy between the sorbitol derivative and the antioxidant. and both components are necessary for maximum activity
- the active components can be added to the cigarette filter by any convenient method, for example by dosing with a solution of the components and allowing the solvent to evaporate.
- the packing material for the filter can be pre-impregnated with the active component before the filter is constructed.
- the test methods were standard in the industry for the investigation of cigarette smoking and analysis of tobacco smoke
- the cigarettes were "smoked" in a smoking machine conforming to the standard US Federal Trade Commission smoking protocol and the smoke was passed through a Cambridge filter, which was weighed before and after the smoking
- the increase in weight of the filter is the total particulate matter (TPM) Nicotine was extracted from the filter by washing with alkaline methanol and estimated using gas chromatography using a nitrogen-phosphorus detection
- the water content of the TPM was measured by extracting the filter with ethanol followed by gas chromatography with conductivity detection Tar is calculated by deducting the nicotine and water contents from the TPM
- Benzo[ ⁇ ]pyrene (BaP) is taken as a representative carcinogen for tobacco smoke and was measured by HPLC analysis (with fluorescence detection) of a cyclohexane extract Cambridge filter
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Cigarettes, Filters, And Manufacturing Of Filters (AREA)
Abstract
A filter for tobacco smoke comprises a free-radical inhibitor, particularly an O-alkylated derivative of 2,4-monofufurylidene sorbitol, together with an antioxidant to reduce the content of polycyclic aromatic hydrocarbons in the smoke.
Description
CIGARETTE FILTERS AND THE LIKE
The present invention is concerned with the treatment of filters for tobacco smoke particularly cigarette filters, to limit the carcinogenic effect of the smoke passed by them to the consumer
Tobacco smoke particularly that from cigarettes, is well-known to contain various components which are either carcinogens or pro-carcinogens One particular class of compounds falling within this category comprises the polycyclic aromatic hydrocarbons (PAH) which are converted by the cytochrome P450 enzyme system in the liver or the lung into oxygenated derivatives which have been shown to be carcinogenic A considerable amount of literature now exists in this field, for example Pryor, et al Science 220:425-427 Pryor. et al Cancer and Free-Radicals in Antimutagenesis and Anticarcinogenesis Mechanisms, Ed D Shankel. et a l ; Plenum Press, New York NY. pages 45-59. Janoff. et a l 1987 Am Rev Respir Dis 1361058-1064 and many others The effect of free-radicals in the smoke has been extensively discussed, for example by Church and Pryor Environ Hea lth Perspect 64111-126 (1985)
GB-A-1044434 discloses the use of 2,4-monofurfurylιdene sorbitol in cigarette filters to reduce the content of PAH in the smoke
In situations where free-radicals are known to cause harm, for example in the skin, the use of free-radical inhibitors is well-known For example EP-B-0 345 362 discloses the use of a particular type of free-radical inhibitor in skin cosmetics The inhibitor in question is chosen from a group of furfurylidene derivatives of sorbitol. in particular 2.4-monofurfurylidene sorbitol and the tetra-O-alkyl derivatives thereof A method for preparing 2,4-monofurfurylιdene sorbitol was disclosed in US-A-3.383.279 comprising gradual addition of furfurol to acidified sorbitol thus forming the 2,4-O-furfurylιdene derivative
We have now investigated the effect of these sorbitol derivatives in other areas Surprisingly, we have now found that the furfurylidene sorbitol derivatives of EP-B-0 345 362. in combinations with certain other components, can be used to impregnate tobacco smoke filters to achieve smoke which has a dramatically reduced content of PAH The mechanism of this action is unknown and unexpected: on the model of previous uses of free-
radical inhibitors, it would be expected that the inhibitor must be present at the site of absorption by the body and not at a remote location The compounds appear to remove mutagenic or carcinogenic compounds from the smoke, but other explanations are possible.
According to the present invention there is thus provided a filter for tobacco smoke comprising means forming a passageway for smoke, characterised in that on a surface of the passageway arranged to contact the smoke there is provided an O-alkylated derivative of 2.4-monofurfurylιdene sorbitol together with an antioxidant. The O-alkylated derivative is desirably a C1-5-alkyl derivative, e.g. the methyl derivative, and the tetra-O-alkyl derivative is preferred.
The filter according to the invention is particularly represented by a cigarette filter, which may have any conventional construction arranged to provide a very large surface area in contact with the smoke passing through, for example packed filaments, open-cell foams, etc.
The free-radical inhibitor may be incorporated in the filter at any effective level, but typically at 2.5-30 mg per filter, especially about 5-20 mg, particularly when tetra-0-methyl 2,4-monofurfurylιdene sorbitol is used
The filter also contains an antioxidant and the ratio by weight of the sorbitol derivative to the antioxidant is desirably from about 1.5:1 to 31, especially, about 2.1 Particularly preferred antioxidants comprise phenolic antioxidants such as tert-butyl-hydroxyanisole (BHA) or tert-butyl-hydroxytoluene (BHT). It appears that there is synergy between the sorbitol derivative and the antioxidant. and both components are necessary for maximum activity
The active components can be added to the cigarette filter by any convenient method, for example by dosing with a solution of the components and allowing the solvent to evaporate. Alternatively, the packing material for the filter can be pre-impregnated with the active component before the filter is constructed.
The following Example illustrates the invention further.
EXAMPLE - Measurement of benzo[α]pyrene and tar levels
In a series of tests, standard cigarettes were used - either Kentucky Reference 1R3F or commercial cigarettes containing no additives in the filter The following additives were investigated
2,4-monofurfurylidene sorbitol tetra-O-methyl ether (FT)
tert-butyl-hydroxyanisole (BHA) The results are summarised in the following table The stated additive dissolved in 40-60 μl diethyl ether, was added in six to ten aliquots using a microsyπnge to inject through the end of the filter Control cigarettes were prepared using diethyl ether only The cigarettes were stored in conditions of controlled humidity and temperature for twenty-four hours and were tested to check that there had been no change in the pressure drop across the filter
The test methods were standard in the industry for the investigation of cigarette smoking and analysis of tobacco smoke The cigarettes were "smoked" in a smoking machine conforming to the standard US Federal Trade Commission smoking protocol and the smoke was passed through a Cambridge filter, which was weighed before and after the smoking The increase in weight of the filter is the total particulate matter (TPM) Nicotine was extracted from the filter by washing with alkaline methanol and estimated using gas chromatography using a nitrogen-phosphorus detection The water content of the TPM was measured by extracting the filter with ethanol followed by gas chromatography with conductivity detection Tar is calculated by deducting the nicotine and water contents from the TPM Benzo[α]pyrene (BaP) is taken as a representative carcinogen for tobacco smoke and was measured by HPLC analysis (with fluorescence detection) of a cyclohexane extract Cambridge filter
As can be seen from the last column, for a 2:1 combination of FT and BHA, a highly significant reduction in BaP was noted. Similar applications in other smoke filters can be envisaged, for example filter cartridges in tobacco pipes. An expert in the art will be
able to foresee several modifications and variations, which will be considered all included within the scope of the present specification.
Claims
1 A filter for tobacco smoke comprising means forming a passageway for smoke, characterised in that on a surface of the passageway arranged to contact the smoke there is provided an O-alkylated derivative of 2,4-monofurfurylidene sorbitol together with an antioxidant
2 A filter according to Claim 1 in which the antioxidant is a phenolic antioxidant
3 A filter according to Claim 2, in which the antioxidant comprises tert-butyl-hydroxyanisole (BHA) or tert-butyl-hydroxytoluene (BHT).
4 A filter according to any of Claims 1 to 3, in which the O-alkylated derivative comprises 24-monofurfurylidene-1,3,5,6-tetra-0-methyl sorbitol
5 A filter according to any of Claims 1 to 4. in which the ratio by weight of the free-radical inhibitor to the antioxidant is from 1.5 1 to 3 1
6 A filter according to Claim 5, in which the ratio is about 21
7 A filter according to any of Claims 1 to 6 in the form of a cigarette filter
8 A filter according to Claim 7 containing 25 to 30 mg of the free-radical inhibitor
9 A filter according to Claim 8 containing about 5 to 20 mg of the free-radical inhibitor
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU35318/95A AU3531895A (en) | 1994-10-07 | 1995-10-06 | Cigarette filters and the like |
| EP95932154A EP0871380A1 (en) | 1994-10-07 | 1995-10-06 | Cigarette filters and the like |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| LU88544 | 1994-10-07 | ||
| LU88544A LU88544A1 (en) | 1994-10-07 | 1994-10-07 | Anticarcinogenic treatment for cigarette filters or the like |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1996010929A1 true WO1996010929A1 (en) | 1996-04-18 |
Family
ID=19731496
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/IB1995/000853 WO1996010929A1 (en) | 1994-10-07 | 1995-10-06 | Cigarette filters and the like |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP0871380A1 (en) |
| AU (1) | AU3531895A (en) |
| LU (1) | LU88544A1 (en) |
| WO (1) | WO1996010929A1 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2772561A1 (en) * | 1997-12-24 | 1999-06-25 | Aromes Et Parfums Franc | USE OF POLYPHENOLIC COMPOUNDS OR DERIVATIVES THEREOF AS SENSORS OF FREE RADICALS IN CIGARETTE FILTERS |
| FR2798302A1 (en) | 1999-09-13 | 2001-03-16 | Frederic Maillard | FILTER COMPRISING NITROGEN HETEROCYCLES, SUCH AS DNA, PARTICULARLY FOR THE FILTRATION OF TOBACCO SMOKE, CIGARETTE COMPRISING SUCH A FILTER |
| GR1004550B (en) * | 2003-05-30 | 2004-05-11 | Γεωργιος Δεληκωνσταντινος | Neutralization of toxic substances in cigarette smoke with a biological filter containing esters of carboxymetallo-porphyrins with bioflavonoids and sugars |
| WO2013060829A3 (en) * | 2011-10-28 | 2013-07-18 | Philip Morris Products S.A. | On-line system and method for nicotine analysis of a smoking article |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1533175A (en) * | 1964-11-25 | 1968-07-19 | Istituto Chemioterapico | Filtration process and element to remove harmful products from tobacco smoke |
| GB2230687A (en) * | 1989-04-28 | 1990-10-31 | Pecsi Dohanygyar | Highly efficient tobacco smoke filter |
| WO1994000138A1 (en) * | 1992-06-26 | 1994-01-06 | Vyrex Corporation | Airborne protectants against oxidative tissue damage |
| JPH0662824A (en) * | 1992-08-12 | 1994-03-08 | Kyodo Nyugyo Kk | Method for removing free radical from tobacco smoke |
-
1994
- 1994-10-07 LU LU88544A patent/LU88544A1/en unknown
-
1995
- 1995-10-06 EP EP95932154A patent/EP0871380A1/en not_active Withdrawn
- 1995-10-06 WO PCT/IB1995/000853 patent/WO1996010929A1/en not_active Application Discontinuation
- 1995-10-06 AU AU35318/95A patent/AU3531895A/en not_active Abandoned
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1533175A (en) * | 1964-11-25 | 1968-07-19 | Istituto Chemioterapico | Filtration process and element to remove harmful products from tobacco smoke |
| GB2230687A (en) * | 1989-04-28 | 1990-10-31 | Pecsi Dohanygyar | Highly efficient tobacco smoke filter |
| WO1994000138A1 (en) * | 1992-06-26 | 1994-01-06 | Vyrex Corporation | Airborne protectants against oxidative tissue damage |
| JPH0662824A (en) * | 1992-08-12 | 1994-03-08 | Kyodo Nyugyo Kk | Method for removing free radical from tobacco smoke |
Non-Patent Citations (1)
| Title |
|---|
| DATABASE WPI Week 9414, Derwent World Patents Index; AN 94-114240 * |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2772561A1 (en) * | 1997-12-24 | 1999-06-25 | Aromes Et Parfums Franc | USE OF POLYPHENOLIC COMPOUNDS OR DERIVATIVES THEREOF AS SENSORS OF FREE RADICALS IN CIGARETTE FILTERS |
| WO1999033365A1 (en) * | 1997-12-24 | 1999-07-08 | Biosynthec | Use of polyphenol compounds or their derivatives as scavengers of free radicals in cigarette filters |
| US8567412B2 (en) | 1997-12-24 | 2013-10-29 | Biosyntec | Use of polyphenol compounds or derivatives thereof as free-radical scavengers in cigarette filters |
| FR2798302A1 (en) | 1999-09-13 | 2001-03-16 | Frederic Maillard | FILTER COMPRISING NITROGEN HETEROCYCLES, SUCH AS DNA, PARTICULARLY FOR THE FILTRATION OF TOBACCO SMOKE, CIGARETTE COMPRISING SUCH A FILTER |
| GR1004550B (en) * | 2003-05-30 | 2004-05-11 | Γεωργιος Δεληκωνσταντινος | Neutralization of toxic substances in cigarette smoke with a biological filter containing esters of carboxymetallo-porphyrins with bioflavonoids and sugars |
| WO2013060829A3 (en) * | 2011-10-28 | 2013-07-18 | Philip Morris Products S.A. | On-line system and method for nicotine analysis of a smoking article |
Also Published As
| Publication number | Publication date |
|---|---|
| AU3531895A (en) | 1996-05-02 |
| LU88544A1 (en) | 1996-04-29 |
| EP0871380A1 (en) | 1998-10-21 |
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