443 



3 



4,830,028 



extending surface thereof with circumscribing plug 

 wrap material 40. 



The filler element 30 is attached to the tobacco rod IS 

 by lipping material 45 which circumscribes both the 

 entire length of the filter element and an adjacent region 

 of the lobncco rod The inner surface of the tipping 

 material 45 is fixedly secured to the outer surfnce of the 

 plug wrap 40 and the outer surface of the wrapping 

 material 25 of the tobacco rod. using a suitable adhesive. 



in order to control the performance characteristics oK 

 the smoking article 



As used herein, the term "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 throujih the sm<»king 

 article and exiting the extreme mouth end portion of the 

 smoking article. For air diluted or ventilated smoking 

 articles of this invention, the amount of air dilution can 



If desired, a ventilated or air diluted smoking article is 10 vary Preferably, the amount of air dilution for a ciga- 



providcd with an air dilution means such as a series of 

 perforations 50 each of which extend through the lip- 

 ping material and plug wrap. 



Typically, the tobacco rod has a length which ranges 

 from about 50 mm to about 85 mm. a circumference of 15 

 .tbout 17 mm to about 27 mm: and the wrapping mate- 

 rial thereof is a conventional cigarette wrapping paper 

 If desired a dual wrapper system can be employed. The 

 tobacco rods and the resulting cigarettes can be manu- 

 factured in any known configuration using known ciga- 20 

 rettc making techniques and equipment. 



Typically, the filter element has a length which 

 ranges from about 20 mm to about 35 mm and a circum- 

 ference of about 19 mm to about 27 mm. The filter 



rctte is greater than about 20 percent, more preferably 

 greater than about 30 percent. The upiwr limit of air 

 dilution for a cigarette typically is lexs than about 80 

 percent, more frequently less than about 60 percent. 



The salt provided from nicotine and an organic acid 

 (also referred to herein as a "nicotine/organic acid 

 salt") requires nicotine as a necessary component The 

 nicotine can be naturally occurring nicotine which is 

 obtained as an extract from nicotineous species (e.g.. 

 tobacco) or synthetic nicotine The nicotine can be 

 l-nicoliiie, d-nicotine, or a mixture of d-iiicotine and 

 l-nicotine. Preferably, the nicotine is employed in rela- 

 tively pure form (e.g., greater than about 15 percent 

 pure, more preferably greater than about 99 percent 



material can be any suitable material such a.s cellulose 25 pure) and is "water clear" in appearance in order to 

 acetate, polypropylene, tobjicco material, or the like avoid or minimize the formation of tarry residues dur- 

 The plug wrap typically is a conventional paper plug ing the subsequent salt formation steps. The nicotine 

 wrap, and can be either air permeable or esseniially air can be purified by distillation or other suitable methods, 

 impermeable. However, if desired, a nonwrapped cellu- Organic acids useful herein are any organic acids or 

 lose acetate filter element can be employed. The various 30 organic compounds that behave as Lewis acids when 

 filter elements suitable for use in this invention can oe contacted with nicotine. Preferred organic acids are 

 manufactured using known cigarette filter making tech- those acids which form salts with nicotine in a 1:1. 2:1 

 niques and equipment. or 3:1 molar ratio (organic acid:nicotine). Examples of 

 The filler material employed in the manufacture of organic acids useful in practicing the present invention 

 the smokable rod can vary Preferably, tlie majority of 35 are aromatic acids including benzoic-type acids and 

 the filler material present in llie smokable rod is a smok- substituted benzoic -type acids, hydroxyacids, heterocy- 

 able material such as tobacco material, or a blend die acids, terpenoid acids, sugar acids such as the pectic 

 thereof with a tobacco substitute material. Examples of acids, amino acids, cycloaliphatic acids, dicarboxylic 

 suitable tobacco materials include lluccured. Burley, acids, aliphatic acids, keto acids, and the like Preferred 

 Md. or Oriental tobaccos: processed tobacco materials 40 organic acids are the straight-chain and branched-chain 

 such as expanded tobaccos, processed tobacco stems. aliphatic acids, more preferably the aliphatic monocar- 

 reconstiluted tobacco materials or reconstituted to- boxylic acids, aiid especially the keto aliphatic mono- 

 hacco materials having varying levels of endogenous carboxylic acids. Examples of suitable organic acids 

 and exogenous nicotine; or blends thereof. If desired, include formic, acetic, propionic, isobutyric, butyric, 

 the tobacco materials can be blended with small 45 alpha-methylbutyric, isovaleric, bela-mcthylvaleric. 

 amounlsof carbonized and/or pyrolyzed materials The caproic, 2-furoic, phenylacetic, heptanoic, octanoic. 

 smokable materials are employed in the form of particu- nonanoic, malic, citric, oxalic, malonic, glycolic, suc- 

 lates as is common in conventional cigarette manufac- cinic, ascorbic, tartaric, fumaric and pyruvic acids, as 

 lure. For example, the smokable filler material can be well as the lower fatly acids (i.e., having carbon chains 

 employed in the foim of strands cut into widths ranging 50 less than Cn) and the higher fatly acids (i.e.. having 

 from about 1/25 inch to about 1/60 inch, preferably carbon chains of C12 to C20). and other such acids The 

 from about 1/30 inch to about 1/40 inch Generally. most preferred organic acid is a gamma keto aliphatic 

 such strands have lengths which range from about 0.25 acid known as levulinic acid (CHjCOCHiCHiCOOH). 

 inch to about 3 inches. Useful organic compounds which exhibit an acid char- 

 Typically, the tipping material circumscribes the 55 acter and which form salts with nicotine include the 

 filter element and an adjacent region of the tobacco rod plienolics such as guaiacol, vanillin, protocatechualde- 

 such that the tipping material extends about 3 mm to hyde, and the like. 



about 6 mm along the length of the tobacco rod. Typi- ' Preferred nicotine/organic acid salts have a molar 



cally, the tipping material is a conventional p.iper tip- ratio of organic acid to nicotine of 11, 2:1 or 31, most 



ping material. The tipping material can have a porosity 60 preferably 3:1 The most preferred salts are totally ion- 



which can vary For example, the tipping material can ized salts of nicotine and the organic acid. For example. 



be essentially air impermeable, air permeable, or be 

 treated (e.g., by mechanical or laser perforation tech- 

 niques) so as to have a region of perforations, openings 

 or vents thereby providing a means for providing air 65 

 dilution to the cigarette. The total surface area of the 

 |>erforalions and the positioning of the perforations 

 along Ihc periphery of the smtiking article can t>e varied 



a particularly preferred sail is provided from 1 mole of 

 nicotine and 3 moles of levulinic acid and has a molar 

 ratio thereof of 1:3. 



The nicotine/organic acid salts are prepared using 

 techniques generally known to those skilled in the art 

 Many of such techniques have been catalogued by Per- 

 fetti in Beitraqe Zur Tbbak/onchung Iiiteniaiionat. Vol. 



