US3547133A - Tobacco having an oxadiazole additive - Google Patents
Tobacco having an oxadiazole additive Download PDFInfo
- Publication number
- US3547133A US3547133A US771981A US3547133DA US3547133A US 3547133 A US3547133 A US 3547133A US 771981 A US771981 A US 771981A US 3547133D A US3547133D A US 3547133DA US 3547133 A US3547133 A US 3547133A
- Authority
- US
- United States
- Prior art keywords
- tobacco
- oxadiazole
- phenyl
- percent
- additive
- 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
- 235000002637 Nicotiana tabacum Nutrition 0.000 title description 28
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 title description 12
- 239000000654 additive Substances 0.000 title description 3
- 230000000996 additive effect Effects 0.000 title description 3
- 244000061176 Nicotiana tabacum Species 0.000 title 1
- 241000208125 Nicotiana Species 0.000 description 27
- 230000000391 smoking effect Effects 0.000 description 11
- 125000000217 alkyl group Chemical group 0.000 description 10
- 239000000779 smoke Substances 0.000 description 10
- 125000003342 alkenyl group Chemical group 0.000 description 9
- 235000019505 tobacco product Nutrition 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- 235000019504 cigarettes Nutrition 0.000 description 7
- 210000004081 cilia Anatomy 0.000 description 6
- 229910052736 halogen Inorganic materials 0.000 description 6
- 150000002367 halogens Chemical class 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 125000000753 cycloalkyl group Chemical group 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 150000004866 oxadiazoles Chemical class 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- VEUMBMHMMCOFAG-UHFFFAOYSA-N 2,3-dihydrooxadiazole Chemical compound N1NC=CO1 VEUMBMHMMCOFAG-UHFFFAOYSA-N 0.000 description 3
- 230000001886 ciliary effect Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 230000029058 respiratory gaseous exchange Effects 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- 125000004663 dialkyl amino group Chemical group 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000019634 flavors Nutrition 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- -1 oxadiazole compound Chemical class 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 210000002345 respiratory system Anatomy 0.000 description 2
- IWXUZMIVJPIVFM-UHFFFAOYSA-N 5-ethyl-3-phenyl-1,2,4-oxadiazole Chemical group O1C(CC)=NC(C=2C=CC=CC=2)=N1 IWXUZMIVJPIVFM-UHFFFAOYSA-N 0.000 description 1
- VRRLZUXQTZOCKJ-UHFFFAOYSA-N 5-methyl-3-phenyl-1,2,4-oxadiazole Chemical group O1C(C)=NC(C=2C=CC=CC=2)=N1 VRRLZUXQTZOCKJ-UHFFFAOYSA-N 0.000 description 1
- LAWKSSDADWQYAX-UHFFFAOYSA-N 5-methyl-3-phenyl-2H-oxadiazole Chemical compound CC1=CN(NO1)C1=CC=CC=C1 LAWKSSDADWQYAX-UHFFFAOYSA-N 0.000 description 1
- 101100264195 Caenorhabditis elegans app-1 gene Proteins 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 235000019506 cigar Nutrition 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 238000011067 equilibration Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000003100 immobilizing effect Effects 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 210000004379 membrane Anatomy 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000033764 rhythmic process Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000007921 spray Substances 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
- A24B15/30—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances
- A24B15/36—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring
Definitions
- This invention relates to improvements in tobacco products, and in particular to cigarettes, cigars and smoking tobacco products having enhanced flavor and physiological properties.
- cilia The bronchial and sinus tracts are lined with mucous membranes which are covered with minute hairlike structures known as cilia. lt is the function of the cilia, which beat in a well coordinated rhythm, to continuously cleanse the breathing passages by moving foreign material trapped in the mucous to the mouth area.
- R is phenyl
- X is hydrogen, halogen or lower alkyl
- R is lower alkyl or alkenyl or phenyl
- the tobacco is treated by applying a solution of the oxadiazole compound in a suitable solvent or as a powder after the tobacco leaf has been processed and aged in the usual manner but before it is converted into the finished smoking article.
- the treated tobacco may contain from about 0.5 percent to l percent of the oxadiazole by weight.
- the preferable level of treatment is usually about 1 percent to 5 percent by weight of the substituted oxadiazole.
- the solvent used for application may be a polar organic solvent, such as an alcohol, ether, etc., a mixture of two or more of the above or an aqueous mixture of one of these.
- the solvent is chosen so as to give good solubility of the oxadiazole and still be readily volatile or easily removed from the tobacco after treatment without interfering with the moisture balance of the final treated tobacco. After the solvent has evaporated and the final moisture adjustment, if any, is made, the tobacco-is converted into its final salable form as a smoking article in the usual manner.
- a smoking tobacco consisting essentially of tobacco and from 0.1 percent to 10 percent by weight of said tobacco of a derivative of oxadiazole of the general formula N-O ⁇ X--RC/ CR' -wherein X is selected from the group consisting of hydrogen, amino, alkylamino, dialkylamino, alkyl, cycloalkyl, alkenyl, and a halogen, said alkyl, cycloalkyl and alkenyl groups having .1 to 12 carbon atoms; R is selected from the group consisting of phenyl, alkyl, cycloalkyl, and alkenyl groups of l to 12 carbon atoms; and R is selected. from the group consisting of phenyl, alkyl, cycloalkyl and alkenyl groups having I to 12 carbon atoms, any of which may be substituted with halogen.
- a smoking tobacco product according to claim 1 wherein said oxadiazole is 3-phenyl-5-methyl-1,2,4-oxadiazole.
- a smoking tobacco product according to claim 1 wherein said oxadiazole is 3-phenyl-5-ethyl-1,2,4-oxadiazole.
- R is phenyl
- R is selected from the group consisting of phenyl, alkyl and alkenyl groups having from I to 12 carbon atoms
- X is selected from the group consisting of hydrogen, halogen, and lower alkyl groups having from 1 to l2 carbon atoms.
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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Manufacture Of Tobacco Products (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US77198168A | 1968-10-30 | 1968-10-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3547133A true US3547133A (en) | 1970-12-15 |
Family
ID=25093537
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US771981A Expired - Lifetime US3547133A (en) | 1968-10-30 | 1968-10-30 | Tobacco having an oxadiazole additive |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3547133A (da) |
| CH (1) | CH505566A (da) |
| DE (1) | DE1954786C3 (da) |
| DK (1) | DK129760B (da) |
| ES (1) | ES372995A1 (da) |
| FI (1) | FI50824C (da) |
| GB (1) | GB1255340A (da) |
| LU (1) | LU59730A1 (da) |
-
1968
- 1968-10-30 US US771981A patent/US3547133A/en not_active Expired - Lifetime
-
1969
- 1969-10-29 DK DK572469AA patent/DK129760B/da not_active IP Right Cessation
- 1969-10-29 ES ES372995A patent/ES372995A1/es not_active Expired
- 1969-10-29 FI FI693100A patent/FI50824C/fi active
- 1969-10-30 LU LU59730D patent/LU59730A1/xx unknown
- 1969-10-30 CH CH1619269A patent/CH505566A/fr not_active IP Right Cessation
- 1969-10-30 GB GB53242/69A patent/GB1255340A/en not_active Expired
- 1969-10-30 DE DE1954786A patent/DE1954786C3/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| LU59730A1 (da) | 1970-03-02 |
| DE1954786A1 (de) | 1970-06-18 |
| DK129760B (da) | 1974-11-18 |
| DE1954786C3 (de) | 1979-10-25 |
| ES372995A1 (es) | 1972-03-16 |
| DE1954786B2 (de) | 1979-03-01 |
| FI50824B (da) | 1976-04-30 |
| DK129760C (da) | 1975-05-05 |
| CH505566A (fr) | 1971-04-15 |
| FI50824C (fi) | 1976-08-10 |
| GB1255340A (en) | 1971-12-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| AS | Assignment |
Owner name: LORILLARD, INC. Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNOR:LOEW S THEATRES INC.;REEL/FRAME:004516/0906 Effective date: 19850819 |