444 



4,830,028 



12. No. 2. p 43 (1983). which i^ incorporated herein by 

 reference Preferably, nicotine/organic acid salts are 

 provided by coniacling nicotine with at least the stoi- 

 chiometric amount of tlie organic acid necessary to 

 form the particular snil under conditions sufncieni to 

 form the sail. 



The preferred salts provided from nicotine and the 

 organic acid generally are essentially non-volatile at 

 conditions under which the smoking articles are manu- 

 factured and stored, however, specific properties of the 

 various salts can vary For example, nicotine/organic 

 acid salts havmg slraiglit-chain or branched-chain ali- 

 phatic acids having less than 20 carbon atoms generally 

 have a molar ratio of 1:3 (nicotine:acid). and generally 



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 addi- 

 tive within the smoking article. For example, the ;iddi- 

 tivc can be applied using syringes or techniques such iis 

 spraying, electrostatic deposition, impregnation, garni- 

 ture injection, spray drying, inclusion and encapsulation 

 techniques, and the like. 



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 desir- 



able that the concentration of the salt within the solu- 



are liquid in form at ambient conditions. Such salts 15 tion not be so dilute that the salt experiences significant 



typically decompose at temperatures less than 100' C, dissociation. Typically, the concentration of salt within 



usually in the range from .iboul 50' C. to about 60° C the solution is about 20 weight percent or more. 



As another example, nicotine/organic acid salts having Suitable solvents for the salts include water, ethanol. q^ 



dicarboxylic organic acids generally have a molar ratio glycerol, propylene glyco.^and the like, as well as coni^ 



of 1:2 (nicotincracid), and generally are solid in form at 20 binations thereof Generally, most nicotine/organic 



ambient conditions. Such salts typically decompose at 

 temperatures in the range from about 90' C. to about 

 120' C. As yet another example, nicotine/organic acid 

 salts having acids contaimng phenyl groups generally 

 have molar ratios of 1 I. . I 2 or 1 :3 (nicotine:acid) Gen- 

 erally such salts are soiid 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 



acid salts are soluble or miscible in such solvents, and 

 the salts do not undergo substantial dissociation when 

 solubilizcd to small amounts. For example, the salt can 

 be hydrated in water without undergoing a significant 

 amount of dissociation. However, salts diluted with 

 substantial amounts of solvent can undergo dissocinlion 

 to some degree to provide for the application of a mix- 

 ture of nicotine/organic acid salt, nicotine and organic 

 acid to the smoking article. Thus, it is possible lo apply 



the flavor or aroma of the aerosol, as numerous organic 30 an additive in the form of nicotine and levulinic acid to 



acids are suitable flavorants. However, whether a par- the smoking article. 



ticular nicotine/organic acid salt acts as a flavoaant If desired, smoking articles can have incorporated 



depends upon the amount of the particular salt em- therein as an additive (i) at least one salt consisting of 



ployed as an additive as well as the flavor threshold of nicotine and an organic acid, and (ii) nicotine. Preferred 



the particular acid entploycd for the salt formation. See, 35 additives of such type include at least one salt having a 



for example, lobaccn Flavoring For Smoking Products. molar ratio of nicotine to organic acid of 1:3. 



by Lcffingwellet al, p. II to 15(1972). Examples of salts The amount of nicotine/organic acid salt or sails 



which can provide flavor and aroma lo the mainstream employed within the smoking article can vary. The 



_aerosol at certain levels include nicotine acetate, nico- amount of salt incorporated within the smoking article 



tine oxalate, nicotine mllate. nicotine isovalerate, nico- 40 depends upon factors such as the placement of the sail 



tine lactate, nicotine citr.ite. nicotine phenylacetatc and within the smoking article, and the configuraiional as- 



nicotine mynstate. Ilowcvcr.itmaybcdcsirabletou.se pects of the smoking article. Configurationat aspects 



salts which provide flavor characteristics lo the ciga- include the composition and characteristics of the filter 



relic al low amounts m order to not provide undesirable material and initial filler blend, the degree of ventilation 



off-tastes or aromas to the cigarette. For example, it 45 of the article, and other such factors. For example, for 



may be desirable to employ certain salts at low enough most cigarettes having filler material comprising a nico- 



levels in order lliat the cigarette does not exhibit taste or tine content of from about I weight percent to about 2 



aroma characteristics which can be perceived as being weight percent, it frequently is desirable to provide salt 



chemical, metallic, bitter, pungent or soapy in nature, or additive to provide a total nicotine conlenl of up to 



as being dissonant to the general organoleptic charac- 50 about 8 weight percent, more frequently up lo about 4 



(eristics associated with tobacco smoke 



The most preferred nicotine/organic acid salt is nico- 

 tine tevulinale. Such a salt can provide a smooth, palat- 

 able character to the cigarette while not providing any 

 significant dis.sonant taste or aroma. If desired, certain 

 amounts of various nicotine/organic acid salts can be 

 blended with nicotine levulinate and employed as the 

 additive of this invention. 



The salts can be incorporated into the smoking article 



weight percent to the cigarette in order lo provide 

 tobacco tasle. strength and satisfaction upon use. Gen- 

 erally, the amount of nicotine/organic acid salt applied 

 lo a cigarette provides from about 0.2 to about 15, pref- 

 erably from about I to about 10 weight percent of salt 

 additive, based on the total weight of ihe sail and the 

 amount of filler material within the cigarette. In certain 

 instances, it is desirable lo employ about 3 weight per- 

 cent of salt additive or more, based on the total weight 



in a variety of places or sites. For example, the salt can (tO of ihe salt and the amount of filler material within the 



be applied lo the filler m.iterial, incorporated within 

 some or all of Ihe filler material, applied to the wrapper 

 C'f 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 heal, or the like. 



Typically, the nicotino/urgunic acid salt additive or 

 additive mixture is incorporated in the smoking article 

 by admixing the additive with the smokable material. 



cigarette. 



The smoking articles of this invention preferably 

 provide a mainstream aerosol exhibiting a pH_ which is 

 essentially equal to or less than that of a similar smoking 

 65 article not having the additive (eg, the nicotine/or- 

 ganic acid salt additive) incorporated therein In certain 

 circumstances, an amount of nicotine/organic acid salt 

 additive is incorporated into the smoking article in 



