Tobacco – Product or device having identifiable constituent to flavor... – Organic compound
Reexamination Certificate
2000-02-15
2001-12-04
Silverman, Stanley S. (Department: 1731)
Tobacco
Product or device having identifiable constituent to flavor...
Organic compound
C131S274000, C131S352000, C544S336000, C544S408000, C426S466000, C426S468000
Reexamination Certificate
active
06325860
ABSTRACT:
FIELD OF INVENTION
The present invention relates to smoking articles such as cigarettes, and in particular to processes for providing a flavorful and aromatic composition for use in smoking articles.
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 glutamine. 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.
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
The present invention provides a method of providing flavorful and aromatic substances which includes heating a mixture comprising a hydroxyketone, a Strecker aldehyde, and ammonium hydroxide. The resultant composition of flavorful and aromatic substances from the reaction includes a substantial quantity of flavorful and aromatic pyrazines that are especially desirable in smoking articles for improving the flavor and aroma properties of the smoking articles. As compared to the conventional methods known in the art, the method of the present invention produces pyrazines at a significantly greater yield. Moreover, a much greater percentage of pyrazines have branched alkyl side chains. As a result, the flavorful and aromatic substances generated in the present invention exhibit decreased volatility in addition to a lower sensory threshold, i.e., powerful sensory attributes at very low concentrations. Thus, smaller quantities of the flavorant and aroma materials of the invention can be used in smoking articles to provide a significantly greater enhancement of flavor and aroma. At the same time, loss of the flavorants during manufacturing and storage of the smoking articles is minimal.
Preferably the hydroxyketones employed in the method of the invention are lower alkyl based hydroxyketones, i.e., compounds comprising 6 carbon atoms or less and containing only carbon, oxygen and hydrogen atoms. Examples of preferred hydroxyketones include 3-hydroxy-2-propanone, 3-hydroxy-2-butanone, dihydroxyacetone. Examples of suitable Strecker aldehyde include acetaldehyde, propanal, 2-methylpropanal, butanal, 2-methylbutanal, 3-methylbutanal, pyruvic aldehyde, hexanal, benzaldehyde and phenylacetaldehyde.
The mixture of hydroxyketone, Strecker aldehyde, and ammonium hydroxide is preferably subjected to heat treatment at a temperature of at least about 75° C. for a period of time sufficiently long so as to provide a composition containing flavorful and aromatic substances, for example from about 5 min. to about 60 min. Although treatment times and temperatures employed in the invention can be widely varied, it is preferable that the mixture is not exposed to such a high temperature for a sufficiently long period of time so as to provide a composition that exhibits a burnt, tarry, overly bitter or highly metallic flavor. Advantageously, the heat treatment is at a temperature of not more than about 150° C.
In a preferred embodiment, the heat treatment of the mixture is conducted in a closed system under pressure. A pressure controlled environment is provided by a pressure chamber or vessel which provides, during heat treatment, containment of the components of the mixture as well as the resultant flavorful and aromatic substances. Heat treatment is preferably conducted at a pressure range of from about 10 psig to about 1,000 psig, normally from about 20 psig to about 500 psig.
The composition, i.e., produced by the method of the invention after heat treatment, contains flavorful and aromatic substances including pyrazines, especially pyrazines having branched alkyl side chains, which exhibit relatively low volatility and potent flavors. The flavorful and aromatic substances are useful as casing or top dressing components for tobacco laminae and cut filler, as well as for other smokable materials. The flavorful and aromatic substances are also useful in those types of smoking articles described in 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 flavorful and aromatic substances are further useful as cigarette filter additives. For example, the flavorful and aromatic compositions can be incorporated into low-density polyethylene and formed into strands, and then incorporated into cigarette filters as described in U.S. Pat. No. 4,281,671 to Bynre et al. and U.S. Pat. No. 4,826,905 to Green, Jr. et al. The flavorful and aromatic compositions also are useful as cigarette wrapper additives; or as additives to the inner regions of cigarette packages (e.g., within a paper/foil laminate of cigarette package or within a low density polyethylene film which is placed within a cigarette package) in order to provide a desirable cigarette aroma and “pack aroma.”
The method of this invention can generate a significantly high yield of flavorants including pyrazines. In addition, because more pyrazines with branched alkyl side chains are produced, the aromatic flavorants generated in the method of
Halpern M.
R. J. Reynolds Tobacco Company
Silverman Stanley S.
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