Tobacco – Product or device having identifiable constituent to flavor... – Organic compound
Reexamination Certificate
2000-02-15
2002-08-27
Fiorilla, Christopher A. (Department: 1731)
Tobacco
Product or device having identifiable constituent to flavor...
Organic compound
C131S276000, C131S275000, C131S278000, C131S369000, C131S359000, C131S352000, C162S139000
Reexamination Certificate
active
06440223
ABSTRACT:
FIELD OF THE INVENTION
The present invention generally relates to smoking articles such as cigarettes, and in particular to smoking articles containing heat activatable flavorant-generating composition and process for making same.
BACKGROUND OF THE INVENTION
Flavor and aroma are important characteristics of smoking articles. To improve the flavor and aroma in smoking articles, flavorful and aromatic substances, including various natural extracts, have been included in smoking articles. For example, various processes for producing and using tobacco extracts, aroma oils and concentrates are proposed in the U.S. Pat. No. 3,136,321 to Davis; U.S. Pat. No. 3,316,919 to Green; U.S. Pat. No. 3,424,171 to Rooker; U.S. Pat. No. 4,421,126 to Gellatly and U.S. Pat. No. 4,506,682 to Mueller and European Patent Publication No. 338,831 to Clapp et al.
U.S. Pat. No. 5,413,122 discloses making a flavorful and aromatic composition from &bgr;-hydroxy &agr;-amino acids by contacting the amino acids with a liquid having an aqueous character. The ratio of liquid to amino acid is 4:1 to 40:1. The mixture is subjected to heat treatment in an enclosed environment to react the amino acids and to thereby provide an aqueous solution of volatile pyrazine flavorants. The resulting aqueous extract containing flavorful pyrazines is then applied to smoking materials to provide flavor and aroma in the smoking articles.
It has also been proposed to react sugars with amino acids to produce desirable flavorants for smoking articles and foods. For example, U.S. Pat. No. 3,478,015 discloses heating a mixture of an amino acid and a sugar in the presence of a polyhydric alcohol and using the reaction product as a flavoring material.
U.S. Pat. No. 3,920,026 describes reacting the amino acid valine with a sugar, other hydroxycarbonyl compound, or dicarbonyl compound under heat treatment in a solvent such as glycerol or propylene glycol and at a temperature of about 100° C. to about 200° C. for about 0.5 to 5 hours. Optionally, a catalyst such as a flavanoid or hydroxyacid is included in the reaction. The reaction products can be used as flavorants in tobacco compositions.
U.S. Pat. No. 4,306,577 discloses the production of flavorants for smoking compositions by reacting reducing sugars and selected amino acids in the presence of ammonium hydroxide and optionally in the presence of an aldehyde in an essentially solvent-free system at a temperature range of 90° C. to 115° C. The selected amino acids are those that have at least two nitrogens such as glutamine, asparagine, lysine, and arginine.
Similarly, U.S. Pat. No. Re. 32,095 discloses reacting a reducing sugar with a source of ammonia in the presence of a trace amount of certain amino acids at a temperature in the range of about 90° C. to about 115° C. for about 5 to 15 minutes. The trace amino acids include aspartic acid, glutamic acid, asparagine, and glutamnine. The weight ratio of sugar to amino acid is in the range of 200-300:1, and the weight ratio of sugar to ammonia source is about 5-15:1.
U.S. Pat. No. 4,286,606 proposes reacting carboxylic acids having a carbon chain of 6 to 26 carbon atoms with a reducing sugar in the presence of ammonia or ammonium hydroxide under heated conditions to produce flavorants for use in smoking articles.
U.S. Pat. No. 4,638,816 describes another method for improving the flavor and aroma characteristics in cigarettes. Glucose is reacted with ammonium hydroxide to produce so called 1-deoxy 1-amino sugars such as 1-deoxy 1-aminoglucose, which are stable and odorless at ambient temperatures. The 1-amino sugar is applied to tobacco fillers. The 1-deoxy 1-amino sugar-impregnated fillers are then subjected to a heat treatment at a high temperature. The heat treatment is said to convert the 1-amino sugar to a “browning” complex such as pyrazine-containing compounds. The cigarettes made thereof are said to have enhanced flavor when smoked.
Although these and other materials can enhance the taste of tobacco products, because of the volatile nature of flavorant and aroma materials, they are often lost at least in part during cigarette manufacturing and packaging steps. Also quantities of the flavorant and aroma materials can diminish during the storage of the finished smoking articles and it is often necessary to increase the initial content of flavorants to compensate.
SUMMARY OF THE INVENTION
In accordance with the present invention, a heat activatable flavorant-generating composition comprising 2-deoxy 2-amino sugars is generated by reacting a mixture consisting essentially of a fructose source, ammonium hydroxide, and optionally diammonium phosphate. The heat activatable flavorant-generating composition is significantly less volatile than conventional flavorful and aromatic substances, and is converted to flavorants such as pyrazine under smoking conditions, i.e., during smoking. The composition can be used as top dressing and incorporated directly into smoking articles without any heating prior to smoking. The resultant smoking articles, when smoked, exhibit highly desirable flavor and aroma properties.
Accordingly, in a first aspect, the present invention relates to a method for improving the flavor and aroma properties in a smoking article. An aqueous mixture of reactable components consisting essentially of a fructose source, ammonium hydroxide, and optionally diammonium phosphate is reacted for a time and under conditions sufficient to provide a heat activatable flavorant-generating composition. In particular, the mixture is exposed to a temperature sufficiently high and for a period of time sufficiently long so as to provide a heat activatable flavorant-generating composition, which comprises one or more 2-deoxy-2-amino sugar compounds. However, because the composition is heat activatable, it is preferable that the reaction mixture is not exposed to such a high temperature for a sufficiently long period of time so as to degrade the amino sugars or to convert them into volatile flavorants. Typically the components of the mixture are allowed to react with each other at a temperature of no greater than about 85° C., preferably no greater than about 50° C. Conveniently, the reaction can be carried out at about room temperature, i.e., about 25° C.
The resultant composition, which contains 2-deoxy 2-amino sugars, can be stored under ambient or refrigerated conditions for substantial time periods of at least about 60 days up to about 4 months without any significant conversion of the materials to volatile flavorants or degradation of the active materials. Moreover, once applied to tobacco materials, the compositions are stabilized by components of the tobacco and can be stored under normal conditions without degradation.
The heat activatable flavorant-generating composition can be directly incorporated into smoking articles without further heat treatment and without heating the tobacco. For example, the composition can be applied as top dressing components for tobacco cut fillers, as well as for other smokable materials. Alternatively, such heat activatable flavorant-generating composition can be incorporated into other types of smoking articles described in, e.g., U.S. Pat. No. 4,708,151 to Shelar; U.S. Pat. No. 4,714,082 to Banerjee et al.; U.S. Pat. No. 4,756,318 to Clearman et al.; and U.S. Pat. No. 4,793,365 to Sensabaugh et al.; as well as European Patent Publication Nos. 212,234 and 277,519.
The heat activatable flavorant-generating composition of this invention typically contains about 0.01 to about 15% by weight of 2-deoxy 2-amino glucose and also has relatively low volatility in both solutions and smoking articles. When the composition is incorporated into a smoking article, flavorful and aromatic substances are generated when the smoking article is smoked. Consequently, the loss of flavorants and aroma substances during the manufacturing process and storage of smoking articles is reduced. Further, the smoking articles can have more consistent and uniform flavorful and aromatic characters because the flavor compositions are
Coleman, III William Monroe
Dominguez Luis Mayan
Dube Michael Francis
Smith Kenneth Wayne
Fiorilla Christopher A.
Halpern Mark
R. J. Reynolds Tobacco Co.
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