Drug – bio-affecting and body treating compositions – Dentifrices
Reexamination Certificate
2000-02-28
2001-05-22
Rose, Shep K. (Department: 1614)
Drug, bio-affecting and body treating compositions
Dentifrices
C424S052000
Reexamination Certificate
active
06235268
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
This invention relates to an antiplaque oral composition containing an alkoxy substituted 2-hydroxy benzophenone which exhibits heightened antibacterial efficacy against plaque causing oral bacteria.
2. The Prior Art
Dental plaque is a soft deposit which forms on teeth as opposed to calculus which is a hard calcified deposit on teeth. Unlike calculus, plaque may form on any part of the tooth surface, particularly at the gingival margin. Hence, beside being unsightly, it is implicated in the occurrence of gingivitis.
It is difficult to predict the efficacy of antibacterial agents when incorporated in oral compositions. For example, cationic antibacterial materials such as chlorhexidine, benzthonium chloride and cetyl pyridinium chloride have been used by the art as antibacterial antiplaque agents in oral compositions. However, such agents are generally not effective when there is also present anionic surfactants required for the effective performance of oral compositions such as toothpaste and mouthrinses. Nonionic antibacterial materials are compatible with anionic ingredients in oral compositions and nonionic halogenated hydroxydiphenyl ethers such as Triclosan have been effectively employed in oral compositions as antibacterial antiplaque agents when admixed with neutral materials such as humectants, abrasives and thickeners used in the formulation of oral compositions. Notwithstanding the antibacterial efficacy of Triclosan, there is a continuing interest in the oral composition field for antibacterial agents which are compatible with anionic surfactants present in such compositions.
It is known to the art, U.S. Pat. No. 3,993,779, that 2-hydroxy benzophenone, and certain alkyl, benzene, halogen and cyclohexyl-substituted 2-hydroxy benzophenones have antibacterial action and are suitable for use as preservatives and disinfectants.
Japanese Patent 03170414 discloses the use of 2-hydroxybenzophenone in toothpaste, for the prevention and treatment of periodontal disorders. Although effective for this purpose, the antiplaque efficacy of the toothpaste containing the hydroxybenzophenone compound is limited and an improvement in its efficacy is required for acceptability in commercial use.
SUMMARY OF THE INVENTION
In accordance with the present invention there is provided an oral antiplaque composition exhibiting heightened antibacterial efficacy against plaque causing oral bacteria which is comprised of an alkoxy substituted 2-hydroxybenzophonone orally acceptable vehicle containing a mixture of an anionic surfactant such as sodium lauryl sulfate and a betaine based surfactant the 4-alkoxysubstituted 2-hydroxy benxophenone having the following formula:
where X, Y, X′ and Y′ represent hydrogen, and lower straight chain or branched alkyl radicals such as C
1
-C
4
radicals such as methyl, ethyl, propyl, isopropyl and butyl, or cycloalkyls such as C
3
-C
6
, such as cyclopropyl, cyclobutyl or cyclohexyl, and R represents lower alkoxy radicals, such as C
1
-C
8
radicals, such as methoxy, ethoxy, propoxy, and octyloxy radicals or combinations thereof and the salts thereof.
As will hereinafter be disclosed, the presence in the oral composition vehicle of the mixture of anionic surfactant and betaine compound provides an unexpected increase the antiplaque efficacy of the oral composition.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
Representative 4-alkoxy substituted 2-hydroxyphenone compounds useful in the practice of the present invention include but are not limited to 2-hydroxy-4-ethoxybenzophenone, 2-hydroxy-4-isopropoxybenzophenone, 2-hydroxy-4-methoxy-4′-t-butyl-benzophenone, 2-hydroxy-4-methoxy-5-methyl-benzophenone. The compound 2-hydroxy-4-methoxybenzophenone is preferred for use in the present invention as the very low toxicity indicated by an LD-50 (oral/rats) of 12.8 g/kg, LD-50 being a standard measure of acute toxicity and defined as lethal dose at which 50% of the rat population dies, Merck Index, Eleventh Ed., Merck & Co., Inc., Rahway, N.J., USA (1989). The fact that the 4-alkoxy substituted 2-hydroxyphenone is non-halogenated suggests that it will be suitable as an ingredient in daily user oral hygiene products such as dentifrice and mouth rinse formulations and will be easily biodegradable.
The 4-alkoxy 2-hydroxy benzophenone is incorporated in the oral compositions of the present invention in a non-toxic, effective antiplaque amount, typically in a range of about 0.003 to about 5%, preferably about 0.005 to about 3% and more preferably about 0.02 to about 1% by weight.
The surfactant mixture present in the compositions of the present invention in addition to their normal functionality to achieve thorough and complete dispersion of the 4-alkoxy substituted 2-hydroxybenzophenone antibacterial agent throughout the oral cavity also unexpectedly increase the antibacterial efficacy of the hydroxybenxophenone compound. The anionic surfactant and betaine based surfactants are present in the composition at a weight ratio of about 0.5:2.0 and preferably about 1:1.
Examples of anionic surfactants useful in the practice of the present invention include water-soluble salts of higher fatty acid monoglyceride monosulfates, such as the sodium salt of the monosulfated monoglyceride of hydrogenated coconut oil fatty acids, higher alkyl sulfates such as sodium lauryl sulfate, alkyl aryl sulfonates such as sodium dodecyl benzene sulfonate, higher alkyl sulfoacetates, higher fatty acid esters of 1,2- dihydroxy propane sulfonate, and the substantially saturated higher aliphatic acyl amides of lower aliphatic amino carboxylic acid compounds, such as those having 12 to 16 carbons in the fatty acid, alkyl or acyl radicals and alkoyl taurines, and the like. Examples of the last mentioned amides and taurates are N-lauroyl sarcosine, and the sodium, potassium and ethanolamine salts of N-lauroyl, N-myristoyl, or N-palmitoyl sarcosine which should be substantially free from soap or similar higher fatty acid material as well as N-methyl-N-cocoyl (or oleoyl or palmitoyl) taurines.
The term “betaine based surfactant” includes amphoteric compounds such as amidobetaine compounds such as cocoamidoethylbetaine, cocoamidopropyl betaine, laurylamido propyl betaine and related compounds as for example fatty acid amido alkyl betaines and mixtures thereof.
The anionic surfactant is incorporated in the oral composition, a concentration of about 0.5 to about 2% by weight and preferably 0.75 to 1% by weight and the betaine based surfactant is incorporated in the oral composition at a concentration of about 0.5 to about 2% by weight and preferably about 0.5 to about 1% by weight.
Linear molecularly dehydrated polyphosphate salts can be optionally employed herein as anticalculus agents. They are well known, being generally employed in the form of their wholly or partially neutralized water soluble alkali metal (e.g. potassium or sodium) or ammonium salts, and any mixtures thereof. Representative examples include sodium tripolyphosphate, monosodium triacid,-, disodium diacid-, trisodium monoacid-, and tetrasodium-pyrophosphates, the corresponding potassium salts and the like. In the present invention, they can be employed in the oral compositions in approximate weight amounts of about 0.1 to about 3%, typically about 1 to about 2.5%, more typically about 1.5 to about 2%, especially about 2%. Preferred anticalculus agents are tetraalkali metal pyrophosphates such as tetrasodium and tetrapotassium pyrophosphates, and mixtures thereof.
Fluoride ions may also be included in the oral compositions of the present invention to provide an anticaries effect. Among these materials are inorganic fluoride salts, such as soluble alkali metal fluoride salts, for example, sodium fluoride, potassium fluoride, sodium monofluorophosphate and sodium hexafluorosilicate. Alkali metal and tin fluorides, such as sodium and stannous fluorides, sodium monofluorophosphate and mixtures thereof, are preferred.
The amount of fluorine-providing salt is generally p
Gaffar Abdul
Scherl Dale S.
Szeles Lori
Xu Tao
Colgate-Palmolive Company
Rose Shep K.
Shapiro Paul
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