US3499452A - Tobacco compositions incorporating novel esters of polyhydroxy compounds - Google Patents
Tobacco compositions incorporating novel esters of polyhydroxy compounds Download PDFInfo
- Publication number
- US3499452A US3499452A US649422A US3499452DA US3499452A US 3499452 A US3499452 A US 3499452A US 649422 A US649422 A US 649422A US 3499452D A US3499452D A US 3499452DA US 3499452 A US3499452 A US 3499452A
- Authority
- US
- United States
- Prior art keywords
- tobacco
- glucose
- compounds
- percent
- 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
Links
- 150000001875 compounds Chemical class 0.000 title description 46
- 235000002637 Nicotiana tabacum Nutrition 0.000 title description 34
- 239000000203 mixture Substances 0.000 title description 9
- 150000002148 esters Chemical class 0.000 title description 8
- 244000061176 Nicotiana tabacum Species 0.000 title 1
- 241000208125 Nicotiana Species 0.000 description 33
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 22
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 19
- 239000008103 glucose Substances 0.000 description 18
- 239000000796 flavoring agent Substances 0.000 description 14
- 235000019634 flavors Nutrition 0.000 description 14
- 230000000391 smoking effect Effects 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- -1 trisaccaharides Chemical class 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical class O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 11
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 235000019504 cigarettes Nutrition 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 9
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 9
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 9
- 235000012141 vanillin Nutrition 0.000 description 9
- 238000000034 method Methods 0.000 description 8
- 239000000779 smoke Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 150000001298 alcohols Chemical class 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 239000000872 buffer Substances 0.000 description 6
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000003463 adsorbent Substances 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 235000019645 odor Nutrition 0.000 description 5
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 4
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 4
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 4
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 4
- 150000002016 disaccharides Chemical class 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 239000012259 ether extract Substances 0.000 description 4
- 150000004676 glycans Chemical class 0.000 description 4
- 150000002334 glycols Chemical class 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 229940041616 menthol Drugs 0.000 description 4
- 150000002772 monosaccharides Chemical class 0.000 description 4
- 229920001282 polysaccharide Polymers 0.000 description 4
- 239000005017 polysaccharide Substances 0.000 description 4
- 238000005507 spraying Methods 0.000 description 4
- 235000019505 tobacco product Nutrition 0.000 description 4
- DKULSTMKCYRQCP-UHFFFAOYSA-N 2-phenylethyl carbonochloridate Chemical compound ClC(=O)OCCC1=CC=CC=C1 DKULSTMKCYRQCP-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 235000009508 confectionery Nutrition 0.000 description 3
- 238000007598 dipping method Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 238000003822 preparative gas chromatography Methods 0.000 description 3
- 238000000197 pyrolysis Methods 0.000 description 3
- 238000007127 saponification reaction Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 150000004043 trisaccharides Chemical class 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 238000013270 controlled release Methods 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 2
- 229910000397 disodium phosphate Inorganic materials 0.000 description 2
- 235000019800 disodium phosphate Nutrition 0.000 description 2
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000003205 fragrance Substances 0.000 description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 2
- 239000001488 sodium phosphate Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 235000019568 aromas Nutrition 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 239000008366 buffered solution Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000000779 depleting effect Effects 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000005454 flavour additive Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000006174 pH buffer Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000012466 permeate Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
- A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
- A24B15/18—Treatment of tobacco products or tobacco substitutes
- A24B15/28—Treatment of tobacco products or tobacco substitutes by chemical substances
- A24B15/281—Treatment of tobacco products or tobacco substitutes by chemical substances the action of the chemical substances being delayed
Definitions
- This invention relates to novel esters of polyhydroxy compounds which may be used a flavorants in tobacco.
- n is an integer from 1 to 4
- R is a radical selected from the group consisting of acyclic alkyls having from 1-12 carbon atoms, vanillin and phenethyl
- R is a radical of a polyhydroxy compound selected from the group consisting of monosaccharides, disaccharides, trisaccharides, polysaccharides and glycols
- X is 'a radical selected from the group consisting of oxygen and sulfur.
- EXAMPLE 2 Tri-O-(phenethoxycarbonyl) glucose Into a reaction flask immersed in a Dry Ice-acetone bath at 75 C. is introduced 48.7 gm. (0.49 mole) of liquid phosgene. A sample of 40.0 gm. (0.33 mole) of phenethyl alcohol, dissolved in 25 ml. of n-hexane, is added to the phosgene over a period of one hour, while the solution is being stirred. The reaction flask is then allowed to reach room temperature and the phosgene allowed to reflux for five hours. At the end of this period the excess phosgene, hexane and the hydrogen chloride formed during the reaction is removed under reduced pressure.
- the crude phenethyl chloroformate is mixed with 100 ml. of ether and the solution washed once with 100 ml. of an aqueous solution containing 11.0 grns. sodium bicarbonate, and twice with 100 ml. portions of water.
- the organic layer is dried over anhydrous sodium sulfate and the solvent evaporated at reduced pressure yielding 59.5 gm. (99% of the theoretical) phenethyl chloroformate.
- the product is purified by column chromatography using silica gel (containing 6% water) as the adsorbent.
- the product is eluted with ether. Evaporation of the solvent deposited 15 gm. of purified mono-O-(vanillinoxycarbonyl) glucose.
- the vanillin content determined by vapor phase chromatography following saponification with alcoholic NaOH, was found to be 35%. Pyrolysis at 300 C. yielded 38.4% vanillin. The theoretical vanillin content based on an average formula of (C H O )C H O is 42.7%.
- This compound upon decomposition produces a strong disagreeable odor and typifies the use of this type of compound for use as fire warning agents.
- the more disagreeable the odor and the more volatile the material the more suitable it will be for this purpose.
- the odor would permeate the surrounding area and give warning of fire to those in the area.
- the compounds may be incorporated in ceiling paints or in wallboard and would serve as fire warning agents if the substance in which they were impregnated were to he heated beyond the point of decomposition of the fire warning agents.
- the amounts of the compounds of this invention which are to be employed as fiavorants for tobacco or as fire warning agents will obviously depend to a great extent upon the nature of the odoriferous material employed and also upon the effect which it is desired to achieve. Obviously, where a very strong odoriferous compound is employed, a lesser amount would have to be used than would be the case where a milder odor is involved.
- the material in which the compound is to be incorporated also affects the amount of the compound to be employed. For instance in tobacco products the amount to be employed will to a large extent be determined not only by the nature of the compound itself but also by the aroma which is sought, i.e. whether a mild flavor or a strong aromatic one is desired. Generally however, we have found that about 0.001 to 0.5 percent of the polyhydroxy compound ester based on the weight of the tobacco is quite satisfactory.
- Cigarettes prepared as described in the above examples Were evaluated for their smoke characteristics by an experienced taste panel. Cigarettes prepared as described in Example 5 exhibited a light sweet fragrance and flavor and produced a balanced smoke flavor spectrum. The light sweet fragrance and flavor were judged to be characteristic qualities of phenethyl alcohol. Cigarettes prepared as described in Example 6 produced a sweet flavor which was judged to be distinctly vanillin-like.
- R" is a radical selected from the group consisting of aliphatic and alicyclic alkyls having from 2 to 10 carbon atoms, vanillin and phenethyl; and R is a polyhydroxy compound selected from the group consisting of monosaccharides, disaccharides, trisaccharides, polysaccharides and glycols.
- the carbonate esters can be decomposed at a rate which is dependent on the temperature and on the pH of the environment thereby releasing fiavorants at a controlled rate.
- the rate of decomposition increases with increasing pH of the medium in contact with the compounds.
- a tobacco smoking article according to claim 1 wherein said compound is tri-O-(phenethoxycarbonyl) glucose.
Landscapes
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Manufacture Of Tobacco Products (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US64942267A | 1967-06-22 | 1967-06-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3499452A true US3499452A (en) | 1970-03-10 |
Family
ID=24604708
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US649422A Expired - Lifetime US3499452A (en) | 1967-06-22 | 1967-06-22 | Tobacco compositions incorporating novel esters of polyhydroxy compounds |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US3499452A (de) |
| CH (1) | CH511791A (de) |
| GB (1) | GB1231054A (de) |
Cited By (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4119106A (en) * | 1975-10-22 | 1978-10-10 | Philip Morris, Incorporated | Flavorant-release resin compositions |
| US4331166A (en) * | 1980-05-02 | 1982-05-25 | Philip Morris, Incorporated | Cigarette |
| US4509537A (en) * | 1983-04-04 | 1985-04-09 | Philip Morris Incorporated | Smoking compositions |
| US4540004A (en) * | 1983-08-01 | 1985-09-10 | Philip Morris, Incorporated | Smoking compositions containing a flavorant-release additive |
| US4804002A (en) * | 1987-05-29 | 1989-02-14 | P. H. Glatfelter Company | Tobacco product containing side stream smoke flavorant |
| US4941486A (en) * | 1986-02-10 | 1990-07-17 | Dube Michael F | Cigarette having sidestream aroma |
| US5144965A (en) * | 1991-05-15 | 1992-09-08 | Philip Morris Incorporated | Smoking compositions containing a vanillin-release additive |
| US5538018A (en) * | 1995-04-05 | 1996-07-23 | Philip Morris Incorporated | Cigarette smoking products containing a vanillin-release additive |
| US5876706A (en) * | 1997-08-18 | 1999-03-02 | S. C. Johnson & Son, Inc. | Air freshener dispenser device with taper candle feature |
| US5919423A (en) * | 1997-08-20 | 1999-07-06 | S. C. Johnson & Son, Inc. | Polymeric wick composition for air freshener candle product |
| US5955034A (en) * | 1997-08-20 | 1999-09-21 | S. C. Johnson & Son, Inc. | Air freshener taper candle product |
| US6013231A (en) * | 1997-12-17 | 2000-01-11 | S. C. Johnson & Son, Inc. | Wick composition for air freshener candle product |
| US6036925A (en) * | 1997-12-17 | 2000-03-14 | S. C. Johnson & Son, Inc. | Air freshener taper candle product |
| US20040040565A1 (en) * | 2002-08-30 | 2004-03-04 | Lixin Xue | Cigarette filters comprising unfunctionalized porous polyaromatic resins for removing gas phase constituents from mainstream tobacco smoke |
| US20110083679A1 (en) * | 2009-10-09 | 2011-04-14 | Philip Morris Usa Inc. | Immobilized flavorants for flavor delivery |
| CN109619644A (zh) * | 2018-12-06 | 2019-04-16 | 河南中烟工业有限责任公司 | 一种烟草加香加料系统异常报警方法 |
| CN116887705A (zh) * | 2021-11-18 | 2023-10-13 | 韩国烟草人参公社 | 新型香味剂、香味剂组合物及含该香味剂组合物的产品 |
| EP4223928A4 (de) * | 2021-11-18 | 2024-05-01 | KT & G Corporation | Tapetenzusammensetzung und tapeten mit emission einer aromatischen komponente durch wärme |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113461536A (zh) * | 2021-08-05 | 2021-10-01 | 四川三联新材料有限公司 | 一种苯乙醇降龙涎碳酸酯潜香物及其制备方法和应用 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2746890A (en) * | 1950-09-14 | 1956-05-22 | Larus & Brother Company Inc | Cigarette device |
| US3047433A (en) * | 1961-10-19 | 1962-07-31 | Philip Morris Inc | Use of diels-alder adducts as tobacco additives |
-
1967
- 1967-06-22 US US649422A patent/US3499452A/en not_active Expired - Lifetime
-
1968
- 1968-06-19 CH CH909068A patent/CH511791A/de not_active IP Right Cessation
- 1968-06-24 GB GB1231054D patent/GB1231054A/en not_active Expired
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2746890A (en) * | 1950-09-14 | 1956-05-22 | Larus & Brother Company Inc | Cigarette device |
| US3047433A (en) * | 1961-10-19 | 1962-07-31 | Philip Morris Inc | Use of diels-alder adducts as tobacco additives |
Cited By (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4119106A (en) * | 1975-10-22 | 1978-10-10 | Philip Morris, Incorporated | Flavorant-release resin compositions |
| US4127601A (en) * | 1975-10-22 | 1978-11-28 | Philip Morris, Incorporated | α-Substituted vinyl menthyl carbonates |
| US4331166A (en) * | 1980-05-02 | 1982-05-25 | Philip Morris, Incorporated | Cigarette |
| US4509537A (en) * | 1983-04-04 | 1985-04-09 | Philip Morris Incorporated | Smoking compositions |
| US4540004A (en) * | 1983-08-01 | 1985-09-10 | Philip Morris, Incorporated | Smoking compositions containing a flavorant-release additive |
| US4941486A (en) * | 1986-02-10 | 1990-07-17 | Dube Michael F | Cigarette having sidestream aroma |
| US4804002A (en) * | 1987-05-29 | 1989-02-14 | P. H. Glatfelter Company | Tobacco product containing side stream smoke flavorant |
| US5144965A (en) * | 1991-05-15 | 1992-09-08 | Philip Morris Incorporated | Smoking compositions containing a vanillin-release additive |
| US5538018A (en) * | 1995-04-05 | 1996-07-23 | Philip Morris Incorporated | Cigarette smoking products containing a vanillin-release additive |
| US5876706A (en) * | 1997-08-18 | 1999-03-02 | S. C. Johnson & Son, Inc. | Air freshener dispenser device with taper candle feature |
| US5919423A (en) * | 1997-08-20 | 1999-07-06 | S. C. Johnson & Son, Inc. | Polymeric wick composition for air freshener candle product |
| US5955034A (en) * | 1997-08-20 | 1999-09-21 | S. C. Johnson & Son, Inc. | Air freshener taper candle product |
| US6013231A (en) * | 1997-12-17 | 2000-01-11 | S. C. Johnson & Son, Inc. | Wick composition for air freshener candle product |
| US6036925A (en) * | 1997-12-17 | 2000-03-14 | S. C. Johnson & Son, Inc. | Air freshener taper candle product |
| US20040040565A1 (en) * | 2002-08-30 | 2004-03-04 | Lixin Xue | Cigarette filters comprising unfunctionalized porous polyaromatic resins for removing gas phase constituents from mainstream tobacco smoke |
| US6863074B2 (en) | 2002-08-30 | 2005-03-08 | Philip Morris Usa Inc. | Cigarette filters comprising unfunctionalized porous polyaromatic resins for removing gas phase constituents from mainstream tobacco smoke |
| US20110083679A1 (en) * | 2009-10-09 | 2011-04-14 | Philip Morris Usa Inc. | Immobilized flavorants for flavor delivery |
| US9185925B2 (en) | 2009-10-09 | 2015-11-17 | Philip Morris Usa Inc. | Immobilized flavorants for flavor delivery |
| US10716324B2 (en) | 2009-10-09 | 2020-07-21 | Philip Morris Usa Inc. | Immobilized flavorants for flavor delivery |
| US11957153B2 (en) | 2009-10-09 | 2024-04-16 | Philip Morris Usa Inc. | Immobilized flavorants for flavor delivery |
| CN109619644A (zh) * | 2018-12-06 | 2019-04-16 | 河南中烟工业有限责任公司 | 一种烟草加香加料系统异常报警方法 |
| CN116887705A (zh) * | 2021-11-18 | 2023-10-13 | 韩国烟草人参公社 | 新型香味剂、香味剂组合物及含该香味剂组合物的产品 |
| EP4223928A4 (de) * | 2021-11-18 | 2024-05-01 | KT & G Corporation | Tapetenzusammensetzung und tapeten mit emission einer aromatischen komponente durch wärme |
| US12473692B2 (en) | 2021-11-18 | 2025-11-18 | Kt&G Corporation | Wallpaper composition and wallpaper from which flavor ingredients are released by heat |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1231054A (de) | 1971-05-05 |
| CH511791A (de) | 1971-08-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| AS | Assignment |
Owner name: UNITED STATES TRUST COMPANY OF NEW YORK, AS COLLAT Free format text: SECURITY INTEREST;ASSIGNOR:LEGGETT GROUP, INC.;REEL/FRAME:004688/0579 Effective date: 19870325 Owner name: UNITED STATES TRUST COMPANY OF NEW YORK, AS COLLAT Free format text: SECURITY INTEREST;ASSIGNOR:LEGGETT GROUP, INC., A CORP. OF DE.;REEL/FRAME:004688/0579 Effective date: 19870325 |