Taste masking of phenolics using citrus flavors

Details Taste masking of phenolics using citrus flavors Taste masking of phenolics using citrus flavors

2001-12-28

2003-03-18

Rose, Shep K. (Department: 1614)

Drug, bio-affecting and body treating compositions

Dentifrices

C424S058000

Reexamination Certificate

active

06534042

ABSTRACT:

BACKGROUND OF THE INVENTION
The present invention relates to oral care products comprising citrus-masked phenolics Oral compositions including mouthwashes and dentifrices containing phenolic compounds have been formulated using one or more of the following: menthol, methyl salicylate, eucalyptol and thymol are well known (U.S. Pat. No. 4,945,087, PCT Int. Appl. Nos. WO 94 16,674; WO 94 07,477; WO 94 18,939). These compositions are characterized by their relatively high alcohol levels (20-27 volume %) which causes them to have negative aesthetics, including excessive “bite” and “bum”. These compositions often have an unpleasant medicinal taste which can be unattractive to consumers. In particular, thymol is the ingredient which contributes most to the unpleasant, medicinal and harsh taste of these compositions although the combination of several phenolics imparts greater negative taste attributes to these compositions than any one phenolic by itself.
Triclosan (2,4,4′-trichloro-2′-hydroxydiphenyl ether) is a phenolic, nonionic antimicrobial agent used in various soap and toiletry products. In the oral care area, triclosan has been used as a plaque-inhibitory agent in various toothpastes and mouthrinses. Triclosan can have an unpleasant, medicinal taste and at sufficient concentration can cause numbing of the tongue and other mucosal and gingival tissues.
Citrus-flavored mouthwashes or dentifrices have been formulated, as well as methods for preparing clear citrus-flavored mouthwashes including for example, U.S. Pat. Nos. 3,876,759 and 4,420,471.
The use of limonene and its derivatives has been used to improve flavor impact and flavor stability in chewing gum compositions (U.S. Pat. No. 4,157,401) as well as in cleaning compositions (U.S. Pat. Nos. 4,511,488 and 4,620,937). Limonene and its derivatives has been shown to have anti-bacterial effects (Zuckerman, I. “Effect of oxidized d-limonene on micro-organisms” Nature, No. 4273, pp. 517, 1951; Yousef C. A. 91 #151896b (1979), Antimicrobial activity of volatile oil components (limonene)). In the oral care area, limonene has been used as a stabilizer to prevent the loss by adsorption of triclosan on the interior surfaces of packaging containers (U.S. Pat. Nos. 5,187,951; 5,135,738; 5,279,813; 5,273,741).
SUMMARY OF INVENTION
The present invention relates to an oral rinse, dentifrice, or oral gel composition comprising:
a) about 0.01 weight % to about 5 weight % of citrus flavor, citrus flavor ingredient, or mixtures thereof;
b) about 0.01 weight % to about 5 weight % of a phenolic, said phenolic selected from the group consisting of menthol, eucalyptol, methyl salicylate, thymol, triclosan, and mixtures thereof; and
C) an orally acceptable carrier.
A preferred embodiment of the present invention relates to an oral rinse, dentifrice, or oral get composition comprising:
a) about 0.01 weight % to about 5 weight % of a citrus flavor, citrus flavor ingredient, or mixtures thereof;
b) about 0.01 weight % to about 5 weight % of a phenolic, said phenolic selected from the group consisting of menthol, eucalyptol, methyl salicylate, thymol, triclosan, and mixtures thereof;
c) about 0.1 weight % to about 70% of a polyol, said polyol selected from the group consisting of glycerol, sorbitol, propylene glycol, butylene glycol, xylitol, cyclodextrin and its derivatives, and mixtures thereof;
d) about 0.01 weight % to about 10 weight % of an oral acceptable surfactant; and
e) an orally acceptable carrier.
A more preferred embodiment of the present invention relates to an oral rinse, dentifrice, or oral gel composition comprising:
a) about 0.01 weight % to about 5 weight % of citrus flavor selected from the group consisting of orange, grapefruit, lemon, mandarin orange, lime, tangerine, and tangelo; citrus flavor ingredient selected from the group consisting of limonene, citral, cadiene, decylaldehyde, linalool, terpineol, linalyl esters, terpinyl acetate, citronellal, &agr;-terpinene, &ggr;-terpinene, 2-dodecanal, &agr;-pinene, &bgr;-pinene, 2-pentenal, decanal, and C
8
to C
10
and C
12
aldehydes, acids, and esters found in citrus flavors; and mixtures thereof;
b) about 0.01 weight % to about 5 weight % of a phenolic, said phenolic selected from the group consisting of menthol, eucalyptol, methyl salicylate, thymol, triclosan, and mixtures thereof;
c) about 0.1 weight % to about 70% of a polyol, said polyol selected from the group consisting of glycerol, sorbitol, propylene glycol, butylene glycol, xylitol, cyclodextrin and its derivatives, and mixtures thereof;
d) about 0.01 weight % to about 10 weight % of an oral acceptable surfactant; and
e) an orally acceptable carrier.
The present invention also relates to a method for retarding development of plaque on a dental surface in the oral cavity of a mammal, comprising administering to said dental surface an amount of said oral rinse, dentifrice, or oral get composition effective in retarding said development of plaque.
The present invention also relates to a method of treating gingivitis, comprising administering to a mammal in need of such treatment an amount of said oral rinse, dentifrice, or oral gel composition effective in treating gingivitis.
The present invention also relates to a method of treating the presence of microorganisms in the oral cavity of a mammal, comprising administering to the mammal in need of such treatment an amount of said oral rinse, dentifrice, or oral gel composition effective in reducing the viable population of said micro-organisms.
DETAILED DESCRIPTION OF THE INVENTION
The dental formulations in this invention comprise oral rinses (e.g. mouthrinses or washes), dentifrices, and oral gels having an effective concentration of phenolic compounds where the unpleasant taste of the phenolics is masked by the addition of citrus flavor oils, aromatics, oleo resins, extracts, or ingredients thereof.
Citrus flavors that may be employed in this invention include natural and synthetic citrus oils, for example, orange, grapefruit, lemon, mandarin orange, lime, Mexican lime, tangerine, tangelo and blends thereof, as well as citrus aromatics, natural oleo resins, and extracts. Examples of products with synthetic flavors include Carrubba A9047 (an orange flavor) and Noville AN110099 (a citrus mint flavor). These flavors typically contain one or more citrus flavor ingredients including, for example, the following: d-limonene, I-limonene, dl-limonene, alpha-citral and beta-citral (geranol), &agr;-terpinene, &ggr;-terpinene, 2-dodecanal, &agr;-pinene, &bgr;-pinene, 2-pentenal, cadiene, decylaldehyde, linalool, terpineol, linalyl esters, terpinyl acetate, citronellal, decanal, as well as C
8
to C
10
and C
12
aldehydes, acids, and esters found in citrus flavors, and mixtures thereof. Either the natural or synthetic form of these ingredients could be used in the composition of the present invention. Certain of these ingredients may provide a better masking effect of the phenolics in these compositions either alone or in combination with other citrus oil components. For example, terpenes found in citrus flavors may be particularly effective in masking the unpleasant phenolic taste found in these compositions. Limonene is the most abundant terpene in citrus flavor and can be found at levels of approximately 90-95% in citrus flavors. It is possible that this terpene could be an important contributor to the masking effect of unpleasant phenolics by citrus oils. One hypothetical mechanism for the masking ability of citrus oils is that the chemical structure of d-limonene and its isomers is similar to several of the phenolics (e.g. thymol, menthol and eucalytol). Thus, limonene may act as an antagonist to phenolic compounds for taste receptors on the tongue.
Phenolics useful in the present invention include menthol, methyl salicylate, eucalyptol, thymol and triclosan, all of which have an antimicrobial activity. Thymol and triclosan are generally considered to have the best antimicrobial activity. Thymol is also an anthelmintic and an antiseptic. For oral rinses of the

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