464 



4,836,224 



7 8 



However, it may be desirable to use organic acids in the art. Many of such techniques have been cata- 



which provide specific flavor characteristics to the logued by Perfelti in Beiirage Zur Tabak/onchung Inter- 



cigarette at low amounts in order to not provide unde- national. Vol. 12, No. 2, p. 43 (1983), which is incorpo- 



sirable ofT-tastcs or aromas to the cigarette. For exam- rated herein by reference. Preferably, nicotine/organic 



pie, it may be desirable to employ certain organic acids 5 acid salts are provided by conucting nicotine with at 



at low enough levels in order that the cigarette does not least the stoichiometric amount of the organic acid 



exhibit taste or aroma characteristics which can be per- necessary to form the particular salt under conditions 



ceived as being chemical, metallic, bitter, pungent or sufTicient to form the salt. 



soapy in nature, or as being dissonant to the general The preferred salts provided from nicotine and the 



organoleptic characteristics associated with tobacco 10 organic acid generally are essentially non-volatile at 



smoke. conditions under which the smoking articles are manu- 



The most preferred organic acid is levulinic acid. faclured and stored, however, specinc properties of the 



Such an organic acid can provide a smooth, palatable various salts can vary. For example, nicotine/organic 



character to the cigarette while not providing any sig- acid salts having straight-chain or branched-chain ali- 



nificant dissonant taste or aroma. If desired, certain 15 phatic acids having less than 20 carbon atoms generally 



amounts of various other organic acids can be blended have a molar ratio of 1:3 (nicotine.acid), and generally 



with levulinic acid and employed as the additive of this are liquid in form at ambient conditions. Such salts 



invention. For example, it is desirable that a majority of typically decompose at temperatures less than 100' C, 



the organic acid additive be levulinic acid. usually in the range from about 50' C. to about 60' C. 



The organic acid additive can be incorporated into 20 As another example, nicotine/organic acid salts having 



the cigarette in a variety of places or sites. For example, dicarboxylic organic acids generally have a molar ratio 



the organic acid or organic acid mixture can be applied of 1:2 (nicotine:acid), and generally are solid in form at 

 to the niler material, incorporated within some or all of ambient conditions. Such salts typically decompose at 



thenilermaterial, applied to the wrapper of the tobacco temperatures in the range from about 90' C. to about 



rod, applied within the glue line of the wrapper of the 2S 120' C. As yet another example, nicoline/organic acid 



tobacco rod, provided within the filter element of the salts having acids containing phenyl groups generally 



cigarette, or the like. If desired, the organic acid addi- have molar ratios of 1:1, 1:2 or 1:3 (nicotine:acid). Gen- 



tive can be incorporated into processed tobaccos during erally such salts are solid in form at ambient conditions. 



the manufacture of such materials. For example, the Such salts typically decompose at temperature in the 



organic acids can be mixed with tobacco extracts or 30 range from about 1 10' C. to about 200' C. 



tobacco aroma oils, and the resulting tobacco material- Numerous nicotine/organic acid salts can improve 



/organic acid mixture can be blended with, mixed with, the flavor or aroma of the aerosol, as numerous organic 



or otherwise used to treat other tobacco(s) or tobacco acids are suitable flavorants. Examples of salts which 



material(s). The organic acid can be applied to the ciga- can provide flavor and aroma to the mainstream aerosol 



rette or be present within the cigarette in nondissociated 35 at certain levels include nicotine acetate, nicotine oxa- 



form and/or in a dissociated (eg., carboxylate) form. late, nicotine malate, nicotine isovalerate, nicotine lac- 



Typically, the organic acid additive is incorporated in tate, nicotine citrate, nicotine phenylacetate and nico- 

 the cigarette by admixing the additive with the tobacco tine myristate. However, it may be desirable to use salts 

 material. The manner or process for applying the addi- which provide flavor characteristics to the cigarette at 

 live can vary depending upon whether the additive is 40 low amounts in order to not provide undesirable off- 

 applied diluted in liquid form, or upon the positioning of tastes or aromas to the cigarette, 

 the additive within the cigarette. For example, the addi- The most preferred nicotine/organic acid salt is nico- 

 tive can be applied using syringes or techniques such as tine levulinate. Such a salt can provide a smooth, palat- 

 spraying, casing, electrostatic deposition, impregnation, able character to the cigarette while not providing any 

 garniture ii^jection, spray drying, inclusion and encap- 45 signiflcant dissonant taste or aroma. If desired, certain 

 sulation techniques, and the like. amounts of various nicotine/organic acid salts can be 



Suitable solvents for the organic acids include water, blended with nicotine levulinate and employed as the 



ethanol, glycerol, propylene glycol, and the like, as well additive to provide cigarettes of this invention. 



as combinations thereof The salts can be incorporated into the cigarette in a 



One or more salts provided from nicotine and an 50 variety of places or sites. For example, the salt can be 



organic acid can be incorporated into the cigarette. The applied to Ihe filler material, incorporated within some 



use of such salts can provide for a cigarette having a or all of the filler material, applied to the wrapper of the 



relatively high nicotine content as well as provide the tobacco rod, applied within the glue line of the wrapper 



organic acid additive. Such salts can be incorporated of the tobacco rod, applied within a region (eg., a cav- 



into cigarettes which include tobacco materials having 55 ity) which is subjected to heal, or Ihe like, 



a wide range of nicotine contents. Typically, the nicoline/organic acid salt additive or 



Preferred nicotine/organic acid salts have a molar additive mixture is incorporated in Ihe cigarette by 



ratio of organic acid to nicotine of 1:1, 2:1 or 3:1, most admixing the additive with the tobacco material, the 



preferably 3:1. The most preferred salts are totally ion- manner or process for applying the additive can vary 



ized salts of nicotine and the organic acid. Such pre- 60 depending upon whether the additive is applied in solid 



ferred ionized salts are those salts wherein both of the or liquid form, or upon the positioning of the additive 



nicotine nitrogen atoms are ionized by the acid hydro- within the cigarette. For example, Ihe additive can be 



gens of the organic acids. For example, a particularly applied using syringes or techniques such as spraying, 



preferred salt is provided from I mole of nicotine and 3 electroslalic deposition, impregnation, garniture injec- 



molesoflevulinicacidandhasamolarratio thereof of 65 lion, spray drying, inclusion and encapsulation lech- 



'•'• niques, and the like. 



The nicotine/organic acid salts conveniently are pre- When the nicoline/organic acid salts are applied 



pared using techniques generally known to those skilled using spraying techniques it is desirable to form a liquid 



