EP0283672B1 - Zigarette - Google Patents

Zigarette Download PDF

Info

Publication number
EP0283672B1
EP0283672B1 EP88101280A EP88101280A EP0283672B1 EP 0283672 B1 EP0283672 B1 EP 0283672B1 EP 88101280 A EP88101280 A EP 88101280A EP 88101280 A EP88101280 A EP 88101280A EP 0283672 B1 EP0283672 B1 EP 0283672B1
Authority
EP
European Patent Office
Prior art keywords
nicotine
cigarette
tobacco
percent
cigarettes
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
Application number
EP88101280A
Other languages
English (en)
French (fr)
Other versions
EP0283672A3 (en
EP0283672A2 (de
Inventor
Jerry Wayne Lawson
Bruce Randall Bullings
Thomas Albert Perfetti
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
RJ Reynolds Tobacco Co
Original Assignee
RJ Reynolds Tobacco Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from US07/012,922 external-priority patent/US4830028A/en
Application filed by RJ Reynolds Tobacco Co filed Critical RJ Reynolds Tobacco Co
Priority to AT88101280T priority Critical patent/ATE94727T1/de
Publication of EP0283672A2 publication Critical patent/EP0283672A2/de
Publication of EP0283672A3 publication Critical patent/EP0283672A3/en
Application granted granted Critical
Publication of EP0283672B1 publication Critical patent/EP0283672B1/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Images

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
    • A24D1/00—Cigars; Cigarettes
    • 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

Definitions

  • the present invention relates to cigarettes and other such types of smoking articles.
  • Cigarettes are popular smoking articles which have a substantially cylindrical rod shaped structure and include a charge of tobacco (i.e., in cut filler form) surrounded by a wrapper such as paper thereby forming a tobacco rod.
  • a wrapper such as paper
  • popular cigarettes include blends of tobacco materials, the majority of the blends having nicotine contents in the range from about 1.2 percent to about 2.25 percent, more frequently from about 1.4 percent to about 2 percent, and most frequently from about 1.6 percent to about 1.8 percent, based on the dry weight of the tobacco materials. It has become desirable to manufacture cigarettes having cylindrical filters aligned in an end-to-end relationship with the tobacco rod.
  • filters are manufactured from fibrous materials such as cellulose acetate and are attached to the tobacco rod using a circumscribing tipping material.
  • Popular cigarettes classified as “full flavor” cigarettes deliver a desirable tobacco taste, flavor and satisfaction to the smoker.
  • the "full flavor” cigarettes deliver about 14 mg or more of FTC "tar” per cigarette.
  • a second classification of popular cigarettes is the “full flavor low tar” classification.
  • the “full flavor low tar” cigarettes deliver from about 8 to about 14 mg of FTC “tar” per cigarette, as well as lower levels of FTC nicotine as compared to “full flavor” cigarettes.
  • a third classification of popular cigarettes is the “ultra low tar” classification. Such “ultra low tar” cigarettes deliver still lower levels of FTC “tar” and nicotine.
  • the “ultra low tar” cigarettes deliver less than about 7 mg of FTC "tar” per cigarette.
  • the "full flavor low tar” and “ultra low tar” cigarettes conventionally have air dilution means such as laser perforations provided in the periphery of the mouthend region thereof, or have filter elements highly efficient for the removal of "tar” and nicotine from the mainstream aerosol.
  • cigarettes having a naturally high nicotine content as cut filler to enhance the tobacco taste, strength and satisfaction of such cigarettes.
  • cigarettes having high nicotine contents eg., which include tobacco blends having natural nicotine contents above about 2.25 weight percent
  • cigarettes having high nicotine contents generally have the propensity to yield unpalatable mainstream smoke which may be perceived as harsh or irritating to the mouth, nose and throat of the user.
  • a cigarette such as an "ultra low tar" cigarette which is capable of delivering a good tobacco taste, strength and smoking satisfaction characteristic of a "full flavor low tar” cigarette while being perceived as palatable but not as overly harsh or irritating.
  • a cigarette such as a "full flavor low tar” cigarette which is capable of delivering a good tobacco taste, strength and smoking satisfaction characteristic of a "full flavor” cigarette while being perceived as palatable but not as overly harsh or irritating.
  • the present invention relates to a smoking article which delivers good tobacco taste while being capable of delivering relatively low amounts of FTC "tar.”
  • Preferred articles of this invention are cigarettes which deliver taste, strength and smoking satisfaction characteristic of "full flavor” cigarettes, and relatively low levels of FTC "tar” characteristic of "full flavor low tar” cigarettes. Also preferred are cigarettes which deliver taste, strength and smoking satisfaction characteristic of "full flavor low tar” cigarettes, and relatively low levels of FTC "tar” characteristic of "ultra low tar” cigarettes.
  • the preferred cigarettes are extremely palatable and provide the perception of having a smooth smoking character (i.e., not providing a perceived harsh or irritating character) relative to a comparable cigarette delivering similar levels of FTC "tar.”
  • cigarettes having i) relatively low FTC "tar" to FTC nicotine ratios, (ii) relatively low FTC carbon monoxide to FTC nicotine ratios, (iii) good tobacco flavor, strength and satisfaction, and (iv) a smooth, palatable smoking character without being overly mild tasting.
  • the levulinic acid is an additive to at least a portion of the smokable material.
  • the acid can be present within the cigarette in a dissociated and/or nondissociated form.
  • the levulinic acid can be present within the cigarette as levulinic acid and/or levulinate ion.
  • dry weight in referring to the smokable material of the smoking article is meant the mass of the smokable material after being dried to constant weight at 214°F (101°C) for 3 hours in a force-draft oven. See, Moseley et al, Ind. Eng. Chem ., Vol. 43, p. 2342 (1951).
  • the term "nicotine content" in referring to the smokable material is meant the mass alkaloid nicotine as analyzed and quantitated by spectroscopic techniques divided by the dry weight of the smokable material analyzed. See, Harvey et al, Tob. Sci. , Vol. 25, p. 131 (1981).
  • the smokable material from which cigarettes of this invention are manufactured conveniently can be a cut filler material composed of one or more tobacco materials having a naturally high nicotine content.
  • the naturally high nicotine content tobacco material(s) can be employed alone or as blends with (i) one or more tobacco materials having low nicotine contents, and/or (ii) one or more tobacco substitutes.
  • cigarettes of this invention include those cigarettes wherein the smokable material thereof exhibits a total nicotine content or blend nicotine content above about 2,25 percent.
  • a cigarette in accord with this invention conveniently can have incorporated therein at least one salt provided from nicotine and an organic acid.
  • the salt is incorporated within the cigarette as an additive.
  • the salt is such that the molar ratio of nicotine to organic acid therein is 1:3.
  • the salt additive includes nicotine levulinate.
  • the particular salt is incorporated into the cigarette in such a manner that during use of the cigarette, the salt is subjected to decomposition conditions.
  • a cigarette of this invention can include a smokable material as well as at least one salt of nicotine and an organic acid as an additive, wherein (i) the nicotine content of the cigarette is above about 2,25 percent, based on the dry weight of the smokable material, and (ii) one of the aforementioned salts is nicotine levulinate.
  • the presence of the nicotine/levulinic acid salt within the cigarette provides improved tobacco taste, strength and smoking satisfaction as well as improved or maintained flavor characteristics to the aerosol during use of the article while avoiding undesirable off-tastes during use.
  • Figure 1 is a longitudinal sectional view of a cigarette of this invention.
  • the cigarette includes a generally cylindrical rod 15 of smokable material 20, such as tobacco cut filler, contained in circumscribing outer wrapping material 25.
  • the rod 15 is hereinafter referred to as a "tobacco rod.”
  • the ends of the tobacco rod are open to expose the smokable material.
  • the cigarette 10 also includes a filter element 30 positioned adjacent one end of the tobacco rod 15 such that the filter element and tobacco rod are axially aligned in an end-to-end relationship, preferably abutting one another.
  • Filter element 30 has a generally cylindrical shape, and the diameter thereof is essentially equal to the diameter of the tobacco rod.
  • the ends of the filter element are open to permit the passage of air and smoke therethrough.
  • the filter element 30 includes filter material 35 which is overwrapped along the longitudinally extending surface thereof with circumscribing plug wrap material 40.
  • the filter element 30 is attached to the tobacco rod 15 by tipping material 45 which circumscribes both the entire length of the filter element and an adjacent region of the tobacco rod.
  • the inner surface of the tipping material 45 is fixedly secured to the outer surface of the plug wrap 40 and the outer surface of the wrapping material 25 of the tobacco rod, using a suitable adhesive.
  • a ventilated or air diluted cigarette is provided with an air dilution means such as a series of perforations 50 each of which extend through the tipping material and plug wrap.
  • the tobacco rod has a length which ranges from about 50 mm to about 85 mm, a circumference of about 17 mm to about 27 mm; and the wrapping material thereof is a conventional cigarette wrapping paper.
  • Suitable cigarette wrapping papers are commercially available as Reference Nos. 719 and 856 from Kimberly-Clark Corp. or as Ecusta Experimental Nos. TOD 01788 and TOD 03363 from Ecusta Corp. If desired a dual wrapper system can be employed.
  • the tobacco rods and the resulting cigarettes can be manufactured in any known configuration using known cigarette making techniques and equipment.
  • the filter element has a length which ranges from about 20 mm to about 35 mm and a circumference of about 17 mm to about 27 mm.
  • the filter material can be any suitable material such as cellulose acetate, polypropylene, tobacco material, or the like. Filter materials having compositions or characteristics so as to exhibit low nicotine filtration efficiencies can be employed.
  • the plug wrap typically is a conventional paper plug wrap, and can be either air permeable or essentially air impermeable. However, if desired, a nonwrapped cellulose acetate filter element can be employed.
  • the various filter elements suitable for use in this invention can be manufactured using known cigarette filter making techniques and equipment.
  • the tipping material circumscribes the filter element and an adjacent region of the tobacco rod such that the tipping material extends about 3 mm to about 6 mm along the length of the tobacco rod.
  • the tipping material is a conventional paper tipping material.
  • the tipping material can have a porosity which can vary.
  • the tipping material can be essentially air impermeable, air permeable, or be treated (eg., by mechanical or laser perforation techniques) so as to have a region of perforations, openings or vents thereby providing a means for providing air dilution to the cigarette.
  • the total surface area of the perforations and the positioning of the perforations along the periphery of the cigarette can be varied in order to control the performance characteristics of the cigarette.
  • air dilution is the ratio (generally expressed as a percentage) of the volume of air drawn through the air dilution means to the total volume of air and aerosol drawn through the cigarette and exiting the extreme mouthend portion of the cigarette.
  • the amount of air dilution can vary.
  • the amount of air dilution for a cigarette is greater than about 20 percent, more preferably greater than about 30 percent.
  • the upper limit of air dilution for a cigarette typically is less than about 80 percent, more frequently less than about 60 percent.
  • the smokable material employed in the manufacture of the tobacco rod can vary.
  • the tobacco material can be engineered in a processed form such as an extruded form (eg., as a foamed extruded rod or extruded into a tubular shape), have the form of filler such as tobacco cut filler, or the like.
  • the tobacco material of cigarettes has the form of cut filler.
  • the terms "filler” or "cut filler” are meant to include tobacco materials which have a form suitable for use in the manufacture of cigarette tobacco rods.
  • filler can include tobacco materials which are blended and are in a form ready for cigarette manufacture.
  • the tobacco filler materials conveniently are employed in the form of strands or shreds as is common in conventional cigarette manufacture.
  • the tobacco cut filler material can be employed in the form of strands cut into widths ranging from about 1/25 inch to about 1/60 inch, preferably from about 1/30 inch to about 1/40 inch.
  • such strands have lengths which range from about 0.25 inch to about 3 inches.
  • Tobacco materials can be cased and top dressed as is conventionally performed during various stages of cigarette manufacture.
  • additives such as flavorants and humectants can be applied to the tobacco material as is commonly done when cigarettes are manufactured.
  • Suitable additives include flavorants such as vanillin, cocoa, licorice, menthol, tobacco aroma oils, tobacco extracts, and the like.
  • Such additives conveniently are applied to the smokable material as top dressing components.
  • the majority of the filler material present in the smokable rod is a tobacco material.
  • the tobacco material can be blended with another smokable material such as a tobacco substitute material.
  • suitable tobacco materials include flue-cured, Burley, Maryland or Oriental tobaccos; processed tobacco materials such as expanded tobaccos, processed tobacco stems, reconstituted tobacco materials or reconstituted tobacco materials having varying levels of endogenous and exogenous nicotine; or blends thereof.
  • the tobacco materials can be blended with small amounts of carbonized and/or pyrolyzed materials.
  • Tobacco material(s) having a naturally high nicotine content conveniently constitute at least a portion of the smokable filler material useful in manufacturing smoking articles of this invention.
  • such useful high nicotine content tobaccos or high nicotine content processed tobaccos have nicotine contents of above about 2.5 percent.
  • the nicotine contents of high nicotine tobacco materials oftentimes are above about 3 percent, frequently above about 4 percent, and in certain circumstances above about 5 percent.
  • the nicotine content of tobacco materials useful in this invention does not exceed about 10 percent.
  • the high nicotine content filler material can vary.
  • tobaccos designated by the U.S.D.A. as Type 35 (One Sucker), Type 36 (Green River) or Type 37 (Virginia Sun Cured) are common tobaccos having a naturally high nicotine content.
  • a cultivar such as Nicotiana rustica often has a natural nicotine content in the range of about 6 percent to about 10 percent.
  • also useful are upper stalk leaves of commercial lines of flue-cured tobacco (designated by the U.S.D.A. as Types 11-14) and Burley tobacco (designated by the U.S.D.A. as Type 31).
  • the natural nicotine content of many tobaccos can depend upon the agronomic conditons under which the tobaccos are grown as well as the particular genetic line of the tobacco.
  • Processed tobacco materials can be employed. Such processed tobaccos can be provided using tobacco reconstitution-type processes. For example, materials can be manufactured using extrusion, cast sheet, fourdrinier or paper making processes. Raw materials used in manufacturing processed tobaccos can include those high nicotine tobaccos described hereinbefore; or various types of tobacco extracts can be employed in the manufacturing steps of the processed tobaccos. Alternatively, processed tobaccos can be manufactured under conditions suitable to provide products having various nicotine levels. If desired, nicotine can be incorporated into the expansion solvents used to provide a volume expanded processed tobacco material having a high nicotine content. A typical expansion process is described in U.S. Patent No. 3,524,451 to Fredrickson. Also, processed tobacco materials include tobaccos or tobacco materials mixed, blended or otherwise treated with tobacco extracts, spray dried tobacco materials or tobacco aroma oils. As such, the processed tobacco materials have high nicotine contents upon completion of the processing steps involved in their preparation or manufacture, and prior to their use in the manufacture of cigarettes.
  • High nicotine tobacco(s) and/or high nicotine processed tobacco(s) can be employed as the tobacco material of the cigarette, as the component(s) of cigarette blends or as portions of the components of cigarette blends.
  • the high nicotine tobacco(s) and/or high nicotine processed tobacco material(s) can be blended with tobacco substitute(s) and/or tobacco material(s) having nicotine contents of less than about 2 percent.
  • the so-called "American blends" having high nicotine contents i.e., total blend nicotine contents above about 2 percent
  • Typical total nicotine contents of the tobacco material or blends of materials from which tobacco rods for cigarettes of this invention are manufactured are greater than about 2.25 percent, generally greater than 2.5 percent, often greater than about 3 percent, frequently greater than about 3.5 percent, and in certain circumstances greater than about 4 percent.
  • Organic acids useful herein are any organic acids or organic compounds that behave as Lewis acids when contacted with nicotine.
  • organic acids useful in practicing the present invention are aromatic acids including benzoic-type acids and substituted benzoic-type acids, hydroxyacids, heterocyclic acids, terpenoid acids, sugar acids such as the pectic acids, amino acids, cycloaliphatic acids, dicarboxylic acids, aliphatic acids, keto acids, and the like.
  • Preferred organic acids are the straight-chain and branched-chain aliphatic acids, more preferably the aliphatic monocarboxylic acids, and especially the keto aliphatic monocarboxylic acids.
  • suitable organic acids include formic, acetic, propionic, isobutyric, butyric, alpha-methylbutyric, isovaleric, beta-methylvaleric, caproic, 2-furoic, phenylacetic, heptanoic, octanoic, nonanoic, malic, citric, oxalic, malonic, glycolic, succinic, ascorbic, tartaric, fumaric and pyruvic acids, as well as the lower fatty acids (i.e., having carbon chains less than C12) and the higher fatty acids (i.e., having carbon chains of C12 to C20), and other such acids.
  • lower fatty acids i.e., having carbon chains less than C12
  • higher fatty acids i.e., having carbon chains of C12 to C20
  • the most preferred organic acid is a gamma keto aliphatic acid known as levulinic acid (CH3COCH2CH2COOH).
  • Levulinic acid also is known as acetylpropionic acid, alpha-ketovaleric acid and 4-oxypentanoic acid.
  • Useful organic compounds which exhibit an acid character include the phenolics such as guaiacol, vanillin, protocatechualdehyde, and the like.
  • organic acids can improve the flavor or aroma of the aerosol, as numerous organic acids are suitable flavorants. However, whether a particular organic acid acts as a flavorant depends upon the amount of the particular organic acid employed as an additive as well as the flavor threshold of the particular acid employed. See, for example, Tobacco Flavoring For Smoking Products , by Leffingwell et al, p. 11 to 15 (1972). However, it may be desirable to use organic acids which provide specific flavor characteristics to the cigarette at low amounts in order to not provide undesirable off-tastes or aromas to the cigarette.
  • certain organic acids at low enough levels in order that the cigarette does not exhibit taste or aroma characteristics which can be perceived as being chemical, metallic, bitter, pungent or soapy in nature, or as being dissonant to the general organoleptic characteristics associated with tobacco smoke.
  • the most preferred organic acid is levulinic acid.
  • Such an organic acid can provide a smooth, palatable character to the cigarette while not providing any significant dissonant taste or aroma.
  • certain amounts of various other organic acids can be blended with levulinic acid and employed as the additive of this invention. For example, it is desirable that a majority of the organic acid additive be levulinic acid.
  • the organic acid additive can be incorporated into the cigarette in a variety of places or sites.
  • the organic acid or organic acid mixture can be applied to the filler material, incorporated within some or all of the filler material, applied to the wrapper of the tobacco rod, applied within the glue line of the wrapper of the tobacco rod, provided within the filter element of the cigarette, or the like.
  • the organic acid additive can be incorporated into processed tobaccos during the manufacture of such materials.
  • the organic acids can be mixed with tobacco extracts or tobacco aroma oils, and the resulting tobacco material/organic acid mixture can be blended with, mixed with, or otherwise used to treat other tobacco(s) or tobacco material(s).
  • the organic acid can be applied to the cigarette or be present within the cigarette in nondissociated form and/or in a dissociated (eg., carboxylate) form.
  • the organic acid additive is incorporated in the cigarette by admixing the additive with the tobacco material.
  • the manner or process for applying the additive can vary depending upon whether the additive is applied diluted in liquid form, or upon the positioning of the additive within the cigarette.
  • the additive can be applied using syringes or techniques such as spraying, casing, electrostatic deposition, impregnation, garniture injection, spray drying, inclusion and encapsulation techniques, and the like.
  • Suitable solvents for the organic acids include water, ethanol, glycerol, propylene glycol, and the like, as well as combinations thereof.
  • One or more salts provided from nicotine and an organic acid can be incorporated into the cigarette.
  • the use of such salts can provide for a cigarette having a relatively high nicotine content as well as provide the organic acid additive.
  • Such salts can be incorporated into cigarettes which include tobacco materials having a wide range of nicotine contents.
  • Preferred nicotine/organic acid salts have a molar ratio of organic acid to nicotine of 1:1, 2:1 or 3:1, most preferably 3:1.
  • the most preferred salts are totally ionized salts of nicotine and the organic acid.
  • Such preferred ionized salts are those salts wherein both of the nicotine nitrogen atoms are ionized by the acid hydrogens of the organic acids.
  • a particularly preferred salt is provided from 1 mole of nicotine and 3 moles of levulinic acid and has a molar ratio thereof of 1:3.
  • nicotine/organic acid salts conveniently are prepared using techniques generally known to those skilled in the art. Many of such techniques have been catalogued by Perfetti in Beitrage Zur Tabak Kauaba International , Vol. 12, No. 2, p. 43 (1983), which is incorporated herein by reference.
  • nicotine/organic acid salts are provided by contacting nicotine with at least the stoichiometric amount of the organic acid necessary to form the particular salt under conditions sufficient to form the salt.
  • the preferred salts provided from nicotine and the organic acid generally are essentially non-volatile at conditions under which the smoking articles are manufactured and stored, however, specific properties of the various salts can vary.
  • nicotine/organic acid salts having straight-chain or branched-chain aliphatic acids having less than 20 carbon atoms generally have a molar ratio of 1:3 (nicotine:acid), and generally are liquid in form at ambient conditions.
  • Such salts typically decompose at temperatures less than 100°C, usually in the range from about 50°C to about 60°C.
  • nicotine/organic acid salts having dicarboxylic organic acids generally have a molar ratio of 1:2 (nicotine:acid), and generally are solid in form at ambient conditions.
  • Such salts typically decompose at temperatures in the range from about 90°C to about 120°C.
  • nicotine/organic acid salts having acids containing phenyl groups generally have molar ratios of 1:1, 1:2 or 1:3 (nicotine:acid).
  • Such salts are solid in form at ambient conditions.
  • Such salts typically decompose at temperatures in the range from about 110°C to about 200°C.
  • Numerous nicotine/organic acid salts can improve the flavor or aroma of the aerosol, as numerous organic acids are suitable flavorants.
  • Examples of salts which can provide flavor and aroma to the mainstream aerosol at certain levels include nicotine acetate, nicotine oxalate, nicotine malate, nicotine isovalerate, nicotine lactate, nicotine citrate, nicotine phenylacetate and nicotine myristate.
  • the most preferred nicotine/organic acid salt is nicotine levulinate.
  • Such a salt can provide a smooth, palatable character to the cigarette while not providing any significant dissonant taste or aroma.
  • certain amounts of various nicotine/organic acid salts can be blended with nicotine levulinate and employed as the additive to provide cigarettes of this invention.
  • the salts can be incorporated into the cigarette in a variety of places or sites.
  • the salt can be applied to the filler material, incorporated within some or all of the filler material, applied to the wrapper of the tobacco rod, applied within the glue line of the wrapper of the tobacco rod, applied within a region (eg., a cavity) which is subjected to heat, or the like.
  • the nicotine/organic acid salt additive or additive mixture is incorporated in the cigarette by admixing the additive with the tobacco material.
  • the manner or process for applying the additive can vary depending upon whether the additive is applied in solid or liquid form, or upon the positioning of the additive within the cigarette.
  • the additive can be applied using syringes or techniques such as spraying, electrostatic deposition, impregnation, garniture injection, spray drying, inclusion and encapsulation techniques, and the like.
  • the nicotine/organic acid salts When the nicotine/organic acid salts are applied using spraying techniques it is desirable to form a liquid solution of the salt in a suitable solvent. Such solutions should exhibit a low enough viscosity to allow for spraying or injecting the solution. However, it is desirable that the concentration of the salt within the solution not be so dilute that the salt experiences significant dissociation. Typically, the concentration of salt within the solution is about 20 weight percent or more.
  • Suitable solvents for the salts include water, ethanol, glycerol, propylene glycol, and the like, as well as combinations thereof.
  • most nicotine/organic acid salts are soluble or miscible in such solvents, and the salts do not undergo substantial dissociation when solubilized to small amounts.
  • the salt can be hydrated in water without undergoing a significant amount of dissociation.
  • salts diluted with substantial amounts of solvent can undergo dissociation to some degree to provide for the application of a mixture of nicotine/organic acid salt, nicotine and organic acid to the cigarette.
  • cigarettes can have incorporated therein as an additive (i) at least one salt consisting of nicotine and an organic acid, and (ii) nicotine.
  • Preferred additives of such type include at least one salt having a molar ratio of nicotine to organic acid of 1:3.
  • the amount of organic acid employed within the cigarette can vary.
  • the amount of organic acid incorporated within the cigarette depends upon factors such as the placement of the organic acid within the cigarette, and the configurational aspects of the cigarette. Configurational aspects include the composition and characteristics of the filter material and initial filler blend, the degree of ventilation of the cigarette, and other such factors.
  • Configurational aspects include the composition and characteristics of the filter material and initial filler blend, the degree of ventilation of the cigarette, and other such factors.
  • the amount of organic acid applied to such a cigarette is greater than about 2 percent, and oftentimes greater than about 3 percent, based on the dry weight of the tobacco filler material within the cigarette.
  • the amount of nicotine/organic acid salt or salts employed within the cigarette can vary.
  • the amount of salt incorporated within the cigarette depends upon factors such as the placement of the salt within the cigarette, and the configurational aspects of the cigarette.
  • salt additive For most cigarettes having tobacco filler material comprising a nicotine content of from about 1 percent to about 2 percent, it frequently is desirable to provide salt additive to provide a total nicotine content of up to about 8 percent, more frequently up to about 4 percent to the cigarette.
  • Such an amount of additive can provide for good tobacco taste, strength and satisfaction upon use.
  • the amount of nicotine/organic acid salt applied to a typical cigarette provides from about 0.25 percent to about 20 percent, preferably from about 1.2 to about 13 percent of salt additive, based on the dry weight of the tobacco filler material within that cigarette. In certain instances, it is desirable to employ about 3.5 percent of salt additive or more, based on the dry weight of the tobacco filler material within the cigarette.
  • the cigarettes of this invention preferably provide a mainstream aerosol exhibiting a pH which is essentially equal to or less than that of a similar cigarette having a low amount (e.g., less than about 0.2 weight percent) of the organic acid additive incorporated therein.
  • an amount of organic acid additive is incorporated into a cigarette in order to reduce the pH of the mainstream aerosol during use thereof.
  • Mainstream aerosol is that aerosol which is drawn through the article and into the mouth of the user.
  • the mainstream aerosol is the mainstream tobacco smoke which includes the combustion and/or pyrolysis products of tobacco material.
  • mainstream aerosol is meant that averaged per-inhalation pH of the whole aerosol as measured using the techniques described by Sensabaugh et al in Tobacco Science , Vol. XI, pp. 25-30 (1967), which is incorporated herein by reference.
  • Typical mainstream aerosol pH for a cigarette ranges from about 4.5 units to about 8.5 units on average per cigarette.
  • a reduction in the pH of mainstream aerosol it is meant a lowering of the average pH of the mainstream aerosol per particular cigarette.
  • Such reduction is provided by the addition of an effective amount of the additive (eg., organic acid additive and/or nicotine/organic acid salt).
  • the reduction in pH is a lowering of the pH by more than about 0.03 pH unit; preferably by more than about 0.08 pH unit.
  • reduction in the pH of the mainstream aerosol does not provide a cigarette which yields mainstream aerosol having a pH significantly below 4.5 units.
  • the presence of the organic acid (which can be provided by the decomposition of the nicotine/organic acid salt during use of the cigarette can introduce a reduction of the pH of the mainstream aerosol depending upon the quantity and type of organic acid which is incorporated therein.
  • a certain balance, mellowing or marrying of the flavors culminate in a fuller bodied tobacco flavor, strength and satisfaction which is delivered to the user.
  • Such a flavor enhancing characteristic is particularly desirable for highly air diluted or "ultra low tar" cigarettes.
  • the pH of the mainstream aerosol is influenced by a number of factors.
  • the pH of mainstream cigarette smoke can be influenced by factors such as the type of tobacco material or blend of tobacco materials employed, the type of processed tobacco (eg., volume expanded tobacco or reconstituted tobacco), the configuration of the cigarette (eg., the filter tow material, the degree of air dilution, the circumference of the cigarette, the type of wrapping material, etc.), the manner of drawing on or puffing the cigarette, and other such factors.
  • Cigarettes of this invention generally deliver from about 0.2 mg to about 3.5 mg, frequently from about 0.3 mg to about 2.5 mg, more frequently from about 0.4 mg to about 1.5 mg of nicotine when smoked under FTC conditions.
  • FTC "tar" to FTC nicotine ratios for cigarettes of this invention are less than about 12, generally less than about 9, frequently less than about 7, and in certain instances less than about 5.
  • FTC "tar” to FTC nicotine ratios for cigarettes of this invention often can range from about 3 to about 6.
  • the FTC "tar” to FTC nicotine ratios of a cigarette having a nicotine/organic acid salt incorporated therein can be lowered by up to about 80 percent of that ratio of similar cigarette not having the salt additive incorporated therein.
  • a salt of nicotine and levulinic acid is provided using the following procedure.
  • levulinic acid Into a 500 ml round bottom flask equipped with a magnetic stirring bar and heating mantle is charged 69.6 g (0.6 mole) of levulinic acid.
  • the levulinic acid is stripped employing a conventional magnetic stirring unit.
  • the levulinic acid is obtained from Aldrich Chemical Co., Catalogue No. 1984-85, p. 672, Compound No. L-200-9, and is employed without further purification.
  • the levulinic acid is heated to about 50°C in order to provide a liquid form thereof, and the liquified component is subjected to stirring.
  • To the liquified levulinic acid is titrated 32.4 g (0.2 mole) of the purified 1-nicotine over about a 20 minute time period. It is preferred to introduce the nicotine to the organic acid in order to provide an environment of excess acid to nicotine and thus promote the formation of salt.
  • a clear, viscous yellow colored material weighing about 100 g results.
  • the product is 1-nicotine levulinate (as determined using infrared spectrometry), and has a nicotine to levulinic acid ratio of 1:3 (as determined by a destructive distillation in a 10 percent sodium hydroxide aqueous solution, subsequent extraction using isopropanol, and gas chromatographic analysis for nicotine).
  • the salt is believed to have a structure substantially as generally described in Fig. 13 of the Perfetti reference, supra .
  • Cigarettes incorporating varying amounts of the 1-nicotine levulinate salt are provided using the following procedure.
  • Cigarettes having lengths of about 99 mm and circumferences of about 24.85 mm have tobacco rod lengths of 68 mm and filter element lengths of 31 mm.
  • the tobacco rod includes a charge of tobacco cut filler weighing about 0.74 g contained in a circumscribing cigarette paper wrap which is sold commercially as 754 Cigarette Paper by Ecusta Corp.
  • the filter element is manufactured using conventional cigarette filter making technology from cellulose acetate tow (2.7 denier per filament, 48,000 total denier) and circumscribing air permeable paper plug wrap having a CORESTA porosity of 26,000 cm/min.
  • the tobacco rod and filter element are aligned in an abutting, end-to-end relationship and secured together using tipping paper having a CORESTA porosity of 3135 ml/min.
  • the tipping paper is adhesively secured to the filter element and the adjacent portion of the tobacco rod.
  • the tipping material circumscribes the length of the filter element and about 3 mm of the length of the tobacco rod.
  • Cigarettes so described are manufactured using a Pilot Cigarette Maker from Hauni-Werke Korber & Co. KG.
  • a ring of mechanically provided perforations extends around the periphery of the cigarette about 13 mm from the extreme mouthend thereof.
  • the perforations so provided yield cigarettes which are 50 percent air diluted.
  • the cigarettes so manufactured are designated Sample Nos. 1, 2, 3 and C-1, corresponding to the sample of filler material from which each cigarette is manufactured.
  • the filler material employed in providing the tobacco rod is in the form of strands cut at about 32 cuts per inch.
  • the initial filler material includes a blend of about 9 percent Burley tobacco, about 41 percent flue-cured tobacco, about 32 percent reconstituted tobacco material, and about 18 percent Oriental tobaccos.
  • the blend has an aqueous casing of glycerin and flavors applied thereto.
  • the first lot is treated with 20 g of the 1-nicotine levulinate additive.
  • the second lot is treated with 60 g of the 1-nicotine levulinate additive.
  • the third lot is treated with 100 g of the 1-nicotine levulinate additive.
  • the fourth lot is not treated with the 1-nicotine levulinate additive and is employed for comparison purposes.
  • the 1-nicotine levulinate additive is applied to cut filler as a spray using a hand sprayer to apply a 1:1 mixture of water and additive.
  • Each of the four lots are separately placed in sealed plastic bags and stored at 70°F for 2 days. Then, the four lots are each mixed with about 480 g of a cut filler mixture of about 75 parts volume expanded Burley tobacco and about 25 parts volume expanded flue-cured tobacco.
  • the volume expanded cut filler mixture is added to each lot using a mixing drum in order to provide a well mixed blend having a moisture content of about 12 percent to about 13 percent.
  • the resulting blend provided from the first lot of filler material has about 1 percent of the 1-nicotine levulinate salt applied thereto (based on the filler conditioned weight) and is designated as Sample No. 1.
  • the resulting blend provided from the second lot of filler material has about 3 percent of the 1-nicotine levulinate salt applied thereto (based on the filler conditioned weight) and is designated as Sample No. 2.
  • the resulting blend provided from the third lot of filler material has about 5 percent of the 1-nicotine levulinate salt applied thereto (based on the filler conditioned weight) and is designated as Sample No. 3.
  • the resulting blend provided from the fourth lot of filler material is not treated with the 1-nicotine levulinate salt additive, is employed for comparison purposes, and is designated as Sample No. C-1.
  • the data in Table I indicate that the various cigarettes have increased nicotine contents and exhibit increased FTC nicotine values as the level of 1-nicotine levulinate is increased.
  • the FTC "tar" to nicotine ratios for the samples decrease as the level of 1-nicotine levulinate is increased.
  • the various cigarettes each exhibit similar "tar" deliveries, carbon monoxide deliveries and puff counts.
  • the samples of the invention i.e., Sample Nos. 1-3
  • the cigarette having about 5 percent salt additive i.e., Sample No. 3
  • Sample No. 3 exhibits greater impact and smoothness as well as less harshness than the cigarette not having salt additive (i.e., Sample No. C-1).
  • Sample No. 2 is not significantly different organoleptically from Sample No. C-1 in terms of harshness and overall taste, even through there is a substantial increase in FTC nicotine of the sample relative to the comparative sample.
  • the nicotine levulinate additive provides for a cigarette having a relatively low FTC "tar" to FTC nicotine ratio while having a smooth (i.e., not overly harsh) taste.
  • Cigarettes incorporating varying amounts of the 1-nicotine levulinate salt are provided using the following procedure.
  • Cigarettes having lengths of about 84 mm and circumferences of about 24.85 mm have tobacco rod lengths of 57 mm and filter element lengths of 27 mm.
  • the tobacco rod includes a charge of tobacco cut filler weighing about 0.49 g contained in a circumscribing cigarette paper wrap which is sold commercially as 854 Cigarette Paper by Ecusta Corp.
  • the filter element is manufactured using conventional cigarette filter making technology from cellulose acetate tow (2.1 denier per filament, 48,000 total denier) and circumscribing non-air permeable paper plug wrap. The tobacco rod and filter element are aligned in an abutting, end-to-end relationship and secured together using a non-air permeable tipping paper.
  • the tipping paper is adhesively secured to the filter element and the adjacent portion of the tobacco rod.
  • the tipping material circumscribes the length of the filter element and about 3 mm of the length of the tobacco rod.
  • Cigarettes so described are manufactured using a Pilot Cigarette Maker from Hauni-Werke Korber & Co. KG.
  • a ring of laser perforations are provided around the periphery of the cigarette about 13 mm from the extreme mouthend thereof.
  • the perforations penetrate through the tipping paper and plug wrap, and are provided using a Laboratory Laser Perforator from Hauni-Werke Korber & Co. KG.
  • the perforated cigarette is 75 percent air diluted.
  • the cigarettes so manufactured are designated Sample Nos. 4, 5, 6 and C-2, corresponding to the sample of filler material from which each cigarette is manufactured.
  • the filler material employed in providing the tobacco rod is in the form of strands cut at about 32 cuts per inch.
  • the initial filler material includes a blend of about 43 percent burley tobacco, about 6 percent flue-cured tobacco, about 19 percent reconstituted tobacco material, and about 32 percent Turkish tobacco.
  • the blend has an aqueous casing of glycerin and flavors applied thereto.
  • the first lot is treated with 60 g of the 1-nicotine levulinate additive.
  • the second lot is treated with 140 g of the 1-nicotine levulinate additive.
  • the third lot is treated with 200 g of the 1-nicotine levulinate additive.
  • the fourth lot is not treated with the 1-nicotine levulinate additive and is employed for comparison purposes.
  • the 1-nicotine levulinate additive is applied to cut filler as a spray using a hand sprayer to apply a 1:1 mixture of water and additive.
  • Each of the four lots are separately placed in sealed plastic bags and stored at 70°F for 2 days. Then, the four lots are each mixed with about 1,060 g of a cut filler mixture of about 35 parts volume expanded burley tobacco and about 65 parts volume expanded flue-cured tobacco,.
  • the volume expanded cut filler mixture is added to each lot using a mixing drum in order to provide a well mixed blend having a moisture content of about 12 percent to about 13 percent.
  • the resulting blend provided from the first lot of filler material has about 3 percent of the 1-nicotine levulinate salt applied thereto (based on the filler conditioned weight) and is designated as Sample No. 4.
  • the resulting blend provided from the second lot of filler material has about 7 percent of the 1-nicotine levulinate salt applied thereto (based on the filler conditioned weight) and is designated as Sample No. 5.
  • the resulting blend provided from the third lot of filler material has about 10 percent of the 1-nicotine levulinate salt applied thereto (based on the filler conditioned weight) and is designated as Sample No. 6.
  • the resulting blend provided from the fourth lot of filler material is not treated with the 1-nicotine levulinate salt additive, is employed for comparison purposes, and is designated as Sample No. C-2.
  • Sample No. C-3 is prepared.
  • Sample No. C-3 is provided by adding nicotine to a cigarette designated as Sample No. C-2.
  • about 30 mg of a 1:1 mixture of ethanol and 85 percent pure 1-nicotine is injected into the cigarette in order to provide a nicotine content of about 3.92 percent to the cigarette.
  • the nicotine/ethanol mixture is incorporated into the tobacco rod by inserting a syringe into the lighting end of the rod and slowly pulling the syringe from the rod while injecting the mixture into the rod.
  • Sample No. 7 is provided by injecting about 10 mg of the previously described 1:1 mixture of ethanol nicotine into a cigarette designated as Sample No. 6 using a syringe in the manner previously described.
  • the cigarette so provided comprises a nicotine levulinate additive as well as an exogenous nicotine additive.
  • the data in Table II indicate that the various cigarettes have increased nicotine contents and exhibit increased FTC nicotine values as the level of 1-nicotine levulinate is increased.
  • the FTC "tar" to nicotine ratios for the samples decrease as the level of 1-nicotine levulinate is increased.
  • the various cigarettes each exhibit similar "tar" deliveries, carbon monoxide deliveries and puff counts.
  • the samples of the invention i.e., Sample Nos. 4-6
  • the pH of the whole smoke of Sample No. C-3 is very much higher than that of any of the other samples.
  • Sample Nos. 5, 6 and C-2 Evaluations of the organoleptic properties of Sample Nos. 5, 6 and C-2 indicate that the cigarette having about 10 percent salt additive (i.e., Sample No. 6) exhibits greater impact and smoothness as well as less harshness than the cigarette not having the salt additive (i.e., Sample No. C-2). All cigarettes sampled provide good tobacco taste and do not exhibit a perceivable chemical off-taste or non-cigarette taste.
  • Sample No. 5 is not significantly different organoleptically from Sample No. C-2 in terms of impact, smoothness, harshness and overall taste even though the sample provides a higher level of FTC nicotine than the comparative sample.
  • Sample No. C-3 is extremely harsh and is not palatable.
  • Sample No. 7 surprisingly exhibits a smooth smoking character and is palatable, even though the sample has a relatively high level of exogenous nicotine incorporated therein.
  • Cigarettes having a high nicotine content and incorporating varying amounts of the levulinic acid are provided using the following procedure.
  • Cigarettes having lengths of about 84 mm and circumferences of about 24.85 mm have tobacco rod lengths of 57 mm and filter element lengths of 27 mm.
  • the tobacco rod includes a charge of tobacco cut filler weighing about 0.76 g contained in a circumscribing cigarette paper wrap which is sold commercially as 854 Cigarette Paper by Ecusta Corp.
  • the filter element is manufactured using conventional cigarette filter making technology from cellulose acetate tow (2.1 denier per filament, 48,000 total denier) and circumscribing air permeable paper plug wrap having a CORESTA porosity of 26,000 cm/min.
  • the tobacco rod and filter element are aligned in an abutting, end-to-end relationship and secured together using porous (air permeable) tipping paper.
  • the tipping paper is adhesively secured to the filter element and the adjacent portion of the tobacco rod.
  • the tipping material circumscribes the length of the filter element and about 4 mm of the length of the tobacco rod.
  • Cigarettes so described are manufactured using a Pilot Cigarette Maker from Hauni-Werke Korber & Co. KG.
  • a ring of mechanically provided perforations extends around the periphery of the cigarette about 13 mm from the extreme mouthend thereof.
  • the perforations so provided yield cigarettes which are 75 percent air diluted.
  • the cigarettes so manufactured are designated Sample Nos. 8, 9, 10 and C-4, corresponding to the sample of filler material from which each cigarette is manufactured.
  • the filler material employed in providing the tobacco rod is in the form of strands cut at about 32 cuts per inch.
  • the initial filler material includes a blend of about 40 percent Burley tobacco having a nicotine content of about 5 percent, about 18 percent flue-cured tobacco having a nicotine content of about 3.5 percent, about 30 percent reconstituted tobacco material having a nicotine content of about 0.5 percent, and 12 percent of an Oriental tobacco blend having a nicotine content of about 0.9 percent.
  • the blend has an aqueous casing of glycerin and flavors applied thereto.
  • the first lot is treated with 120 g of the levulinic acid additive.
  • the second lot is treated with 280 g of the levulinic acid additive.
  • the third lot is treated with 400 g of the levulinic acid additive.
  • the fourth lot is not treated with the levulinic acid additive and is employed for comparison purposes.
  • the levulinic acid additive is applied to cut filler as a spray using a hand sprayer as a mixture of water and additive.
  • the quantity of water of the water/additive mixture is adjusted to attain a final cut filler moisture content of about 15 percent.
  • Each of the four lots are separately placed in sealed plastic bags and stored at 70°F for 2 days. Then, the four lots are each mixed with about 2,000 g on a dry weight basis, of a cut filler mixture of about 35 parts volume expanded Burley tobacco having a nicotine content of about 4 percent, and about 65 parts volume expanded flue-cured tobacco having a nicotine content of about 4 percent.
  • the volume expanded cut filler mixture is added to each lot using a mixing drum in order to provide a well mixed blend having a moisture content of between about 12 percent and about 13 percent.
  • the resulting blend provided from the first lot of filler material has about 3 percent of the levulinic acid applied thereto (based on the filler dry weight) and is designated as Sample No. 8.
  • the resulting blend provided from the second lot of filler material has about 7 percent of the levulinic acid applied thereto (based on the filler dry weight) and is designated as Sample No. 9.
  • the resulting blend provided from the third lot of filler material has about 10 percent of the levulinic acid applied thereto (based on the filler dry weight) and is designated as Sample No. 10.
  • the resulting blend provided from the fourth lot of filler material is not treated with the levulinic acid additive, is employed for comparison purposes, and is designated as Sample No. C-4.
  • the reduction in the smoke pH of the samples of the invention is indicative of a substantial increase in the hydronium ion concentration of the tobacco smoke.
  • Such an increase in the hydronium ion concentration of the mainstream smoke is sufficient to provide a change in the organoleptic quality of the smoke.
  • Organoleptic evaluation of the samples indicates that the cigarettes of the invention are smooth smoking while the control sample is very harsh.
  • the mildness of Sample Nos. 8 and 9 is considered comparable.
  • the cigarettes of the invention yield good tobacco taste, strength and smoking satisfaction.
  • the control sample is very strong, and the overpowering sensation provided thereby is not satisfying.
  • Cigarettes incorporating varying amounts of the levulinic acid are provided using the following procedure.
  • Cigarettes having lengths of about 84 mm and circumferences of about 24.85 mm have tobacco rod lengths of 57 mm and filter element lengths of 27 mm.
  • the tobacco rod includes a charge of tobacco cut filler weighing about 0.82 g contained in a circumscribing cigarette paper wrap which is sold commercially as 856 Cigarette Paper by Ecusta Corp.
  • the filter element is manufactured using conventional cigarette filter making technology from cellulose acetate tow (2.7 denier per filament, 48,000 total denier) and circumscribing air permeable paper plug wrap having a CORESTA porosity of about 26,000 cm/min.
  • the tobacco rod and filter element are aligned in an abutting, end-to-end relationship and secured together using essentially air impermeable tipping paper.
  • the tipping paper is adhesively secured to the filter element and the adjacent portion of the tobacco rod.
  • the tipping material circumscribes the length of the filter element and about 4 mm of the length of the tobacco rod.
  • Cigarettes so described are manufactured using a Pilot Cigarette Maker from Hauni-Werke Korber & Co. KG.
  • a ring of laser perforations extends around the periphery of the cigarette about 13 mm from the extreme mouthend thereof.
  • the perforations so provided yield cigarettes which are 50 percent air diluted.
  • the cigarettes so manufactured are designated Sample Nos. 11, 12, 13 and C-5, corresponding to the sample of filler material from which each cigarette is manufactured.
  • the filler material employed in providing the tobacco rod is in the form of strands cut at about 32 cuts per inch.
  • the initial filler material includes a blend of about 31 percent Burley tobacco having a nicotine content of about 5 percent, about 20 percent flue-cured tobacco having a nicotine content of about 3.5 percent, about 31 percent reconstituted tobacco material having a nicotine content of about 0.5 percent, and 18 percent of an Oriental tobacco blend having a nicotine content of about 0.9 percent.
  • the blend has an aqueous casing of glycerin and flavors applied thereto.
  • the first lot is treated with 40 g of the levulinic acid additive.
  • the second lot is treated with 120 g of the levulinic acid additive.
  • the third lot is treated with 200 g of the levulinic acid additive.
  • the fourth lot is not treated with the levulinic acid additive and is employed for comparison purposes.
  • the levulinic acid additive is applied to cut filler as a spray using a hand sprayer as a mixture of water and additive.
  • the quantity of water of the water/additive mixture is adjusted to attain a final cut filler moisture content of about 15 percent.
  • Each of the four lots are separately placed in sealed plastic bags and stored at 70°F for 2 days. Then, the four lots are each mixed with about 880 g on a dry weight basis, of a cut filler mixture of about 35 parts volume expanded Burley tobacco having a nicotine content of about 4 percent, and about 65 parts volume expanded flue-cured tobacco having a nicotine content of about 4 percent.
  • the volume expanded cut filler mixture is added to each lot using a mixing drum in order to provide a well mixed blend having a moisture content of between about 12 percent and about 13 percent.
  • the resulting blend provided from the first lot of filler material has about 1 percent of the levulinic acid applied thereto (based on the filler dry weight) and is designated as Sample No. 11.
  • the resulting blend provided from the second lot of filler material has about 3 percent of the levulinic acid applied thereto (based on the filler dry weight) and is designated as Sample No. 12.
  • the resulting blend provided from the third lot of filler material has about 5 percent of the levulinic acid applied thereto (based on the filler dry weight) and is designated as Sample No. 13.
  • the resulting blend provided from the fourth lot of filler material is not treated with the levulinic acid additive, is employed for comparison purposes, and is designated as Sample No. C-5.
  • Organolepic evaluation of the samples indicates that the cigarettes of the invention are smooth smoking while the control sample is very harsh.
  • the mildness of Sample Nos. 12 and 13 is considered comparable.
  • the cigarettes of the invention yield good tobacco taste, strength and smoking satisfaction.
  • the control sample is very strong, and the overpowering sensation provided thereby is not satisfying.
  • Cigarettes incorporating varying amounts of the levulinic acid are provided using the following procedure.
  • Cigarettes having lengths of about 84 mm and circumferences of about 24.85 mm have tobacco rod lengths of 57 mm and filter element lengths of 27 mm.
  • the tobacco rod includes a charge of tobacco cut filler weighing about 0.82 g contained in a circumscribing cigarette paper wrap which is sold commercially as 856 Cigarette Paper by Ecusta Corp.
  • the filter element is manufactured using conventional cigarette filter making technology from cellulose acetate tow (2.7 denier per filament, 48,000 total denier) and circumscribing air permeable paper plug wrap having a CORESTA porosity of about 26,000 cm/min.
  • the tobacco rod and filter element are aligned in an abutting, end-to-end relationship and secured together using essentially air impermeable tipping paper.
  • the tipping paper is adhesively secured to the filter element and the adjacent portion of the tobacco rod.
  • the tipping material circumscribes the length of the filter element and about 4 mm of the length of the tobacco rod.
  • Cigarettes so described are manufactured using a Pilot Cigarette Maker from Hauni-Werke Korber & Co. KG.
  • the cigarettes so manufactured are designated Sample Nos. 14, 15, 16 and C-6, corresponding to the sample of filler material from which each cigarette is manufactured.
  • the filler materials employed in providing the tobacco rods for Sample Nos. 14, 15, 16 and C-6 are the filler materials described for Sample Nos. 11, 12, 13 and C-5, respectively.
  • Organolepic evaluation of the samples indicates that the cigarettes of the invention are smooth smoking while the control sample is very harsh.
  • the mildness of Sample Nos. 15 and 16 is considered comparable.
  • the cigarettes of the invention yield good tobacco taste, strength and smoking satisfaction.
  • the control sample is very strong, and the overpowering sensation provided thereby is not satisfying.

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)
  • Cigarettes, Filters, And Manufacturing Of Filters (AREA)

Claims (11)

  1. Zigarette mit rauchbarem Material, welches von einem begrenzenden äußeren Umhüllungsmaterial aufgenommen wird, wobei die Zigarette
    (i) ein Verhältnis von FTC "Teer" zu FTC Nikotin von weniger als 9;
    (ii) einen Nikotingehalt von mehr als 2,25 %, bezogen auf das Trockengewicht des rauchbaren Materials, und
    (iii) im rauchbaren Material mehr als 1 %, bezogen auf dessen Trockengewicht, Lävulinsäure in dissoziierter und/oder nicht-dissoziierter Form
    hat.
  2. Zigarette nach Anspruch 1, deren Nikotingehalt, bezogen auf das Trockengewicht des rauchbaren Materials, größer als 2,5 % ist.
  3. Zigarette nach Anspruch 1, deren Nikotingehalt, bezogen auf das Trockengewicht des rauchbaren Materials, größer als 3 % ist.
  4. Zigarette nach Anspruch 1, 2 oder 3, deren Lävulinsäuregehalt, bezogen auf das Trockengewicht des rauchbaren Materials, größer als 2 % ist.
  5. Zigarette nach Anspruch 1, 2 oder 3, deren Lävulinsäuregehalt, bezogen auf das Trockengewicht des rauchbaren Materials, größer als 3 % ist.
  6. Zigarette nach einem oder mehreren der vorstehenden Ansprüche, in der im wesentlichen die gesamte Lävulinsäure in nicht-dissoziierter Form vorliegt.
  7. Zigarette nach einem oder mehreren der Ansprüche 1 bis 5, in der mindestens ein Teil der Lävulinsäure in Form von Nikotinlävulinat vorliegt.
  8. Zigarette nach einem oder mehreren der Ansprüche 1 bis 7, welche ein Verhältnis von FTC "Teer" zu FTC Nikotin von weniger als 7 hat.
  9. Zigarette nach Anspruch 1, welche ein Verhältnis von FTC "Teer" zu FTC Nikotin von 3 bis 6 hat.
  10. Zigarette nach einem oder mehreren der vorstehenden Ansprüche, bei der das rauchbare Material eine Mischung aus Tabakmaterialien ist.
  11. Zigarette nach einem oder mehreren der vorstehenden Ansprüche, welche ein Filterelement besitzt, in dem sich wenigstens ein Teil der Lävulinsäure befindet.
EP88101280A 1987-02-10 1988-01-29 Zigarette Expired - Lifetime EP0283672B1 (de)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT88101280T ATE94727T1 (de) 1987-02-10 1988-01-29 Zigarette.

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US07/012,922 US4830028A (en) 1987-02-10 1987-02-10 Salts provided from nicotine and organic acid as cigarette additives
US07/137,987 US4836224A (en) 1987-02-10 1987-12-24 Cigarette
US137987 1987-12-24
US12922 2001-10-22

Publications (3)

Publication Number Publication Date
EP0283672A2 EP0283672A2 (de) 1988-09-28
EP0283672A3 EP0283672A3 (en) 1989-07-12
EP0283672B1 true EP0283672B1 (de) 1993-09-22

Family

ID=26684181

Family Applications (1)

Application Number Title Priority Date Filing Date
EP88101280A Expired - Lifetime EP0283672B1 (de) 1987-02-10 1988-01-29 Zigarette

Country Status (11)

Country Link
EP (1) EP0283672B1 (de)
CN (1) CN1014486B (de)
AU (1) AU598342B2 (de)
BR (1) BR8800560A (de)
DE (1) DE3884246T2 (de)
DK (1) DK69488A (de)
ES (1) ES2043692T3 (de)
FI (1) FI880489A (de)
MY (1) MY103056A (de)
NO (1) NO880564L (de)
PT (1) PT86729B (de)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10231484B2 (en) 2007-12-18 2019-03-19 Juul Labs, Inc. Aerosol devices and methods for inhaling a substance and uses thereof
US10244793B2 (en) 2005-07-19 2019-04-02 Juul Labs, Inc. Devices for vaporization of a substance
US10517530B2 (en) 2012-08-28 2019-12-31 Juul Labs, Inc. Methods and devices for delivering and monitoring of tobacco, nicotine, or other substances
US10653180B2 (en) 2013-06-14 2020-05-19 Juul Labs, Inc. Multiple heating elements with separate vaporizable materials in an electric vaporization device
US10834964B2 (en) 2005-07-19 2020-11-17 Juul Labs, Inc. Method and system for vaporization of a substance
US10952468B2 (en) 2013-05-06 2021-03-23 Juul Labs, Inc. Nicotine salt formulations for aerosol devices and methods thereof
US11478021B2 (en) 2014-05-16 2022-10-25 Juul Labs, Inc. Systems and methods for aerosolizing a vaporizable material
US11660403B2 (en) 2016-09-22 2023-05-30 Juul Labs, Inc. Leak-resistant vaporizer device

Families Citing this family (42)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2935707A (en) * 1958-05-12 1960-05-03 Emerson Radio & Phonograph Cor Inductive tuning device
DE3837930C1 (de) * 1988-11-09 1989-09-28 H.F. & Ph.F. Reemtsma Gmbh & Co, 2000 Hamburg, De
US4920990A (en) * 1988-11-23 1990-05-01 R. J. Reynolds Tobacco Company Cigarette
GB8918556D0 (en) * 1989-08-15 1989-09-27 British American Tobacco Co Improvements relating to smoking articles
US5441060A (en) * 1993-02-08 1995-08-15 Duke University Dry powder delivery system
DE4332019C2 (de) * 1993-09-16 1996-06-13 Reemtsma H F & Ph Ventilierte Filtercigarette
US7726320B2 (en) 2006-10-18 2010-06-01 R. J. Reynolds Tobacco Company Tobacco-containing smoking article
CN101536636B (zh) * 2008-03-17 2011-04-20 湖北省烟草科研所 一种用混合物降低烟碱含量的方法
US20110268809A1 (en) * 2010-04-28 2011-11-03 Paul Andrew Brinkley Nicotine-Containing Pharmaceutical Compositions
CA2824970C (en) 2011-02-11 2016-05-03 Batmark Limited Inhaler component
US9078473B2 (en) 2011-08-09 2015-07-14 R.J. Reynolds Tobacco Company Smoking articles and use thereof for yielding inhalation materials
CN103070477B (zh) * 2013-01-16 2014-06-11 湖南中烟工业有限责任公司 氨基丙醇类化合物的应用
CN103126073B (zh) * 2013-03-05 2015-03-11 湖南中烟工业有限责任公司 一种可降低卷烟主流烟气中焦油含量的滤棒纤维基材添加剂及应用
CN103141941B (zh) * 2013-03-05 2015-02-11 湖南中烟工业有限责任公司 一种可降低卷烟主流烟气中酚类化合物的沟槽滤棒纤维素纸添加剂及应用
US10279934B2 (en) 2013-03-15 2019-05-07 Juul Labs, Inc. Fillable vaporizer cartridge and method of filling
CN103190702B (zh) * 2013-04-27 2014-02-26 红塔辽宁烟草有限责任公司 制造具有提高卷烟感官保润性能软胶囊的方法及其应用
MY178840A (en) 2013-05-21 2020-10-20 Philip Morris Products Sa Aerosol comprising distributing agent and a medicament source
KR102665932B1 (ko) 2013-12-05 2024-05-13 쥴 랩스, 인크. 에어로졸 장치를 위한 니코틴 액제 및 그 방법
CN110664012A (zh) 2013-12-23 2020-01-10 尤尔实验室有限公司 蒸发装置系统和方法
US10058129B2 (en) 2013-12-23 2018-08-28 Juul Labs, Inc. Vaporization device systems and methods
US10076139B2 (en) 2013-12-23 2018-09-18 Juul Labs, Inc. Vaporizer apparatus
US10159282B2 (en) 2013-12-23 2018-12-25 Juul Labs, Inc. Cartridge for use with a vaporizer device
USD842536S1 (en) 2016-07-28 2019-03-05 Juul Labs, Inc. Vaporizer cartridge
US20160366947A1 (en) 2013-12-23 2016-12-22 James Monsees Vaporizer apparatus
USD825102S1 (en) 2016-07-28 2018-08-07 Juul Labs, Inc. Vaporizer device with cartridge
US9839238B2 (en) 2014-02-28 2017-12-12 Rai Strategic Holdings, Inc. Control body for an electronic smoking article
GB2535427A (en) 2014-11-07 2016-08-24 Nicoventures Holdings Ltd Solution
GB2532062A (en) * 2014-11-07 2016-05-11 Nicoventures Holdings Ltd Container
KR102574658B1 (ko) 2014-12-05 2023-09-05 쥴 랩스, 인크. 교정된 투여량 제어
CN104432479B (zh) * 2014-12-25 2015-12-30 中国烟草总公司郑州烟草研究院 一种改进的低焦油混合型卷烟
CN104489898A (zh) * 2014-12-25 2015-04-08 中国烟草总公司郑州烟草研究院 一种低焦油烟碱比卷烟
SG10202108578XA (en) 2016-02-11 2021-09-29 Juul Labs Inc Securely attaching cartridges for vaporizer devices
UA125687C2 (uk) 2016-02-11 2022-05-18 Джуул Лебз, Інк. Заповнювальний картридж випарного пристрою та способи його заповнення
US10405582B2 (en) 2016-03-10 2019-09-10 Pax Labs, Inc. Vaporization device with lip sensing
USD849996S1 (en) 2016-06-16 2019-05-28 Pax Labs, Inc. Vaporizer cartridge
USD848057S1 (en) 2016-06-23 2019-05-07 Pax Labs, Inc. Lid for a vaporizer
USD851830S1 (en) 2016-06-23 2019-06-18 Pax Labs, Inc. Combined vaporizer tamp and pick tool
USD836541S1 (en) 2016-06-23 2018-12-25 Pax Labs, Inc. Charging device
CN111050572A (zh) * 2017-09-05 2020-04-21 日本烟草产业株式会社 烟草材料
USD887632S1 (en) 2017-09-14 2020-06-16 Pax Labs, Inc. Vaporizer cartridge
GB201903287D0 (en) * 2019-03-11 2019-04-24 Nicoventures Trading Ltd Composition
CN114886154A (zh) * 2022-05-27 2022-08-12 河南中烟工业有限责任公司 一种用于改善滤嘴通风卷烟干燥感的添加剂及其制备方法

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2766145A (en) * 1954-07-26 1956-10-09 Reynolds Tobacco Co R Tobacco
US3136319A (en) * 1962-12-13 1964-06-09 Brown & Williamson Tobacco Smoking tobacco product having menthyl keto ester additive
GB1111007A (en) * 1965-03-30 1968-04-24 Imp Tobacco Co Ltd Improvements in cigarettes and paper therefor
US3313307A (en) * 1965-04-13 1967-04-11 Reynolds Tobacco Co R Tobacco
FR2182367A5 (en) * 1972-04-28 1973-12-07 Shaw Alec Smoking tobacco processing - for modification of aroma or other characteristics
FR2403035B1 (fr) * 1977-09-16 1988-03-04 Gallaher Ltd Procede d'impression d'une enveloppe pour produit cylindrique a fumer, et produits obtenus
US4489739A (en) * 1982-05-24 1984-12-25 Kimberly-Clark Corporation Smokable tobacco composition and method of making
EP0103970A3 (de) * 1982-08-20 1985-05-22 LAWRENCE, Peter Robin Broughton Salze von Aminen und Erzeugnisse welche diese Salze enthalten

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10244793B2 (en) 2005-07-19 2019-04-02 Juul Labs, Inc. Devices for vaporization of a substance
US10834964B2 (en) 2005-07-19 2020-11-17 Juul Labs, Inc. Method and system for vaporization of a substance
US10231484B2 (en) 2007-12-18 2019-03-19 Juul Labs, Inc. Aerosol devices and methods for inhaling a substance and uses thereof
US10517530B2 (en) 2012-08-28 2019-12-31 Juul Labs, Inc. Methods and devices for delivering and monitoring of tobacco, nicotine, or other substances
US10952468B2 (en) 2013-05-06 2021-03-23 Juul Labs, Inc. Nicotine salt formulations for aerosol devices and methods thereof
US10653180B2 (en) 2013-06-14 2020-05-19 Juul Labs, Inc. Multiple heating elements with separate vaporizable materials in an electric vaporization device
US11478021B2 (en) 2014-05-16 2022-10-25 Juul Labs, Inc. Systems and methods for aerosolizing a vaporizable material
US11660403B2 (en) 2016-09-22 2023-05-30 Juul Labs, Inc. Leak-resistant vaporizer device

Also Published As

Publication number Publication date
EP0283672A3 (en) 1989-07-12
AU1146988A (en) 1988-08-11
PT86729B (pt) 1992-05-29
CN1039530A (zh) 1990-02-14
DK69488A (da) 1988-08-11
CN1014486B (zh) 1991-10-30
AU598342B2 (en) 1990-06-21
EP0283672A2 (de) 1988-09-28
NO880564D0 (no) 1988-02-09
FI880489A (fi) 1988-08-11
FI880489A0 (fi) 1988-02-03
DK69488D0 (da) 1988-02-10
BR8800560A (pt) 1988-09-27
PT86729A (pt) 1988-03-01
NO880564L (no) 1988-08-11
DE3884246D1 (de) 1993-10-28
ES2043692T3 (es) 1994-01-01
MY103056A (en) 1993-04-30
DE3884246T2 (de) 1994-03-03

Similar Documents

Publication Publication Date Title
EP0283672B1 (de) Zigarette
US4836224A (en) Cigarette
US5031646A (en) Cigarette
US4920990A (en) Cigarette
US4941486A (en) Cigarette having sidestream aroma
Hoffmann The changing cigarette, 1950-1995
US4942888A (en) Cigarette
US5092353A (en) Cigarette
US5074321A (en) Cigarette
US4759380A (en) Filter cigarette having segmented sections
KR20190069583A (ko) 흡연 물품
JP7530975B2 (ja) タバコ組成物
US20090050165A1 (en) Herbal and tobacco filler composition for biri, cigarette and the like
JPH01281071A (ja) 不燃たばこ代用品
US6030462A (en) Smoking article having increased amino acid content
US4719929A (en) Non-tobacco smoking materials
CA1332335C (en) Citrus-flavored tobacco articles
US5370139A (en) Tobacco treatment process
EP0972456B1 (de) Regulierer für tabakraucharoma
US5076294A (en) Filter cigarette
US5060673A (en) Agglomerated matrix for cigarettes and method for making same
US20230157350A1 (en) Delivery systems and methods of making the same
US5076295A (en) Cigarette filter
HU215714B (hu) Ventilált füstszűrős cigaretta
CN111918563A (zh) 吸烟制品

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

AK Designated contracting states

Kind code of ref document: A2

Designated state(s): AT BE CH DE ES FR GB GR IT LI LU NL SE

PUAL Search report despatched

Free format text: ORIGINAL CODE: 0009013

AK Designated contracting states

Kind code of ref document: A3

Designated state(s): AT BE CH DE ES FR GB GR IT LI LU NL SE

17P Request for examination filed

Effective date: 19890922

17Q First examination report despatched

Effective date: 19901005

GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Kind code of ref document: B1

Designated state(s): AT BE CH DE ES FR GB GR IT LI LU NL SE

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: GR

Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT

Effective date: 19930922

REF Corresponds to:

Ref document number: 94727

Country of ref document: AT

Date of ref document: 19931015

Kind code of ref document: T

REF Corresponds to:

Ref document number: 3884246

Country of ref document: DE

Date of ref document: 19931028

ITF It: translation for a ep patent filed
ET Fr: translation filed
REG Reference to a national code

Ref country code: ES

Ref legal event code: FG2A

Ref document number: 2043692

Country of ref document: ES

Kind code of ref document: T3

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: GB

Effective date: 19940129

Ref country code: AT

Effective date: 19940129

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: SE

Effective date: 19940130

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: LU

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 19940131

Ref country code: LI

Effective date: 19940131

Ref country code: ES

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 19940131

Ref country code: CH

Effective date: 19940131

Ref country code: BE

Effective date: 19940131

REG Reference to a national code

Ref country code: GR

Ref legal event code: FG4A

Free format text: 3009781

PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT

BERE Be: lapsed

Owner name: R.J. REYNOLDS TOBACCO CY

Effective date: 19940131

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: NL

Effective date: 19940801

26N No opposition filed
NLV4 Nl: lapsed or anulled due to non-payment of the annual fee
GBPC Gb: european patent ceased through non-payment of renewal fee

Effective date: 19940129

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: FR

Effective date: 19940930

REG Reference to a national code

Ref country code: CH

Ref legal event code: PL

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: DE

Effective date: 19941001

REG Reference to a national code

Ref country code: FR

Ref legal event code: ST

REG Reference to a national code

Ref country code: GR

Ref legal event code: MM2A

Free format text: 3009781

EUG Se: european patent has lapsed

Ref document number: 88101280.1

Effective date: 19940810

REG Reference to a national code

Ref country code: ES

Ref legal event code: FD2A

Effective date: 19990301

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: IT

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 20050129