Method and compositions for imparting cooling effect to tobacco products

Abstract

The present invention relates to smoking articles such as cigarettes, and in particular to a method and composition for providing a cooling effect to cigarettes. The tobacco rod of the cigarette contains a compound that imparts a cooing effect and sensation of freshness to tobacco smoke.

1 . A smoking article, the smoking article comprising: 
 a smokable material; and    a compound comprising a cyclic α-keto enamine, wherein the cyclic α-keto enamine is capable of imparting a cooling sensation to an oral cavity of a smoker upon inhalation of a smoke stream from the smoking article.    
   
   
       2 . The smoking article of  claim 1 , wherein the smokable material comprises a tobacco.  
   
   
       3 . The smoking article of  claim 1 , wherein the cyclic α-keto enamine is deposited on the smokable material.  
   
   
       4 . The smoking article of  claim 1 , wherein the cyclic α-keto enamine is selected from the group consisting of 3-methyl-2-(1-piperidinyl)-2-cyclopenten-1-one, 3-methyl-2-diethylamino-2-cyclopenten-1-one, 5-methyl-2-(1-piperidinyl)-2-cyclopenten-1-one, 5-methyl-2-diethylamino-2-cyclopenten-1-one, 5-methyl-2-dibutylamino-2-cyclopenten-1-one, 5-methyl-2-dihexylamino-2-cyclopenten-1-one, 5-ethyl-2-(1-pyrrolidinyl)-2-cyclopenten-1-one, (E)-4,5-dimethyl-2-(1-pyrrolidinyl)-2-cyclopenten-1-one, 3,5-dimethyl-2-(1-pyrrolidinyl)-2-cyclopenten-1-one, 3,4-dimethyl-2-(1-pyrrolidinyl)-2-cyclopenten-1-one, 3-(1-pyrrolidinyl)-2-cyclopenten-1-one, 2-methyl-3-(1-pyrrolidinyl)-2-cyclopenten-1-one, 1-pyrrolidinyl)-2-cyclohexen-1-one, 3-methyl-2-(1-pyrrolidinyl)-2-cyclohexen-1-one, 3,5,5-trimethyl-2-(1-pyrrolidinyl)-2-cyclohexen-1-one, 6-methyl-2-(1-pyrrolidinyl)-2-cyclohexen-1-one, 4,4,6-trimethyl-2-(1-pyrrolidinyl)-2-cyclohexen-1-one, 5-methyl-2-(1-morpholino)-2-cyclopenten-1-one, (S)-5-methyl-2-(2-methoxycarbony1-1-pyrrolidinyl)-2-cyclopenten-1-one, (S)-3-methyl-2-(2-carboxy-1-pyrrolidinyl)-2-cyclopenten-1-one, 2,5-dimethyl-4-(1-pyrrolidinyl)-3-(2H)-furanone, 4,5-dimethyl-3-(1-pyrrolidinyl)-2-(5H)-furanone, and mixtures thereof.  
   
   
       5 . The smoking article of  claim 1 , wherein the cyclic α-keto enamine comprises 3-methyl-2-(1-pyrrolidinyl)-2-cyclopenten-1-one.  
   
   
       6 . The smoking article of  claim 1 , wherein the cyclic α-keto enamine comprises 5-methyl-2-(1-pyrrolidinyl)-2-cyclopenten-1-one.  
   
   
       7 . The smoking article of  claim 1 , wherein the cyclic α-keto enamine comprises 5-methyl-4-(1-pyrrolidinyl)-3-(2H)-furanone.  
   
   
       8 . The smoking article of  claim 1 , wherein the cyclic α-keto enamine comprises 4-methyl-3-(1-pyrrolidinyl)-2-(5H)-furanone.  
   
   
       9 . The smoking article of  claim 1 , comprising a cigarette.  
   
   
       10 . The smoking article of  claim 1 , further comprising a filter.  
   
   
       11 . The smoking article of  claim 10 , wherein the filter comprises an activated charcoal or an activated carbon.  
   
   
       12 . A method of providing a smoke stream from a cigarette, wherein the smoke stream is capable of imparting a cooling sensation to an oral cavity, the method comprising: 
 providing a cigarette, the cigarette comprising a tobacco charge and a compound comprising a cyclic α-keto enamine;    combusting the tobacco charge, whereby a smoke stream is produced, the smoke stream comprising the cyclic α-keto enamine; and    inhaling the smoke stream, whereby a cooling sensation is imparted to an oral cavity.    
   
   
       13 . A smoking article, the smoking article comprising: 
 a smokable material; and    a compound selected from the group consisting of a carboxamide, a mentane glycerol ketal, a menthyl ester, an alkyl-substituted urea, a sulfonamide, a phosphine oxide, wherein the compound is capable of imparting a cooling sensation to an oral cavity of a smoker upon inhalation of a smoke stream from the smoking article.    
   
   
       14 . The smoking article of  claim 13 , wherein the carboxamide has a chemical formula corresponding to:  
     
       
         
         
             
             
         
       
     
   
   
       15 . The smoking article of  claim 13 , wherein the mentane glycerol ketal has a chemical formula corresponding to:  
     
       
         
         
             
             
         
       
     
   
   
       16 . The smoking article of  claim 13 , wherein the menthyl ester has a chemical formula corresponding to:  
     
       
         
         
             
             
         
       
     
   
   
       17 . The smoking article of  claim 13 , wherein the alkyl-substituted urea has a chemical formula corresponding to:  
     
       
         
         
             
             
         
       
     
   
   
       18 . The smoking article of  claim 13 , wherein the sulfonamide has a chemical formula corresponding to:  
     
       
         
         
             
             
         
       
     
   
   
       19 . The smoking article of  claim 13 , wherein the phosphine oxide has a chemical formula corresponding to:  
     
       
         
         
             
             
         
       
     
   
   
       20 . The smoking article of  claim 13 , wherein the smoking material comprises a tobacco.