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WO1994027566A1 - Arome peppermint ameliore pour produits d'hygiene orale - Google Patents

Arome peppermint ameliore pour produits d'hygiene orale Download PDF

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Publication number
WO1994027566A1
WO1994027566A1 PCT/US1994/005118 US9405118W WO9427566A1 WO 1994027566 A1 WO1994027566 A1 WO 1994027566A1 US 9405118 W US9405118 W US 9405118W WO 9427566 A1 WO9427566 A1 WO 9427566A1
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WIPO (PCT)
Prior art keywords
oil
oral hygiene
liquid oral
composition
weight
Prior art date
Application number
PCT/US1994/005118
Other languages
English (en)
Inventor
Mamoun Hussein
Shirley A. Barcelon
Edward Carlin
Original Assignee
Warner-Lambert Company
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Warner-Lambert Company filed Critical Warner-Lambert Company
Priority to AU68285/94A priority Critical patent/AU6828594A/en
Publication of WO1994027566A1 publication Critical patent/WO1994027566A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/342—Alcohols having more than seven atoms in an unbroken chain
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—Esters of carboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • A61K8/922—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof of vegetable origin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/52—Stabilizers

Definitions

  • This invention relates to oral hygiene products such as mouthwashes with an improved flavoring oil, in particular, with heavily rectified peppermint oil which is free of undesirable fractions so as to effect an uncharacteristically clean mint taste.
  • essential oils exhibiting penetrating characteristic flavors are well known in cosmetic, hygienic and pharmaceutical as well as food products.
  • Natural flavor oils are generally used in the form of products of a single distillation without further processing. For example, this kind of basic flavorant product has been quite suitable for use in gums and confections. Since natural flavor oil products are poorly soluble in water, conventional liquid oral hygiene products utilize relatively high concentrations of alcohol for aiding in the solubilization and taste perception of such flavorant essential oils.
  • the natural extracts of essential oils contain terpenes, including sesquiterpenes. These terpene components of natural flavor oils are undesirable since they tend to oxidize upon exposure to air resulting in the
  • the present invention is directed to an improved liquid oral hygiene composition which contains heavily rectified mint flavor oils producing a less bitter clean taste and a perception of acceptable clarity thus lowering the need for surfactant agents.
  • the present invention utilizes a rectification or fractionation process that does not require
  • the mint oils are also rendered more hydrophilic resulting in superior flavor perception attributes and lowering the requirement of alcohol in the oral vehicle.
  • Rectification removes undesirable fractions from the oil containing resins. Rectification or redistillation of flavorants or essential oils is applied to varying degrees depending on end use. It may vary from light to heavy. Light redistillation of the oils is required to meet USP or FCC specifications.
  • rectifications of flavor oils are used for oral hygiene preparations, liqueurs, boiled and high quality
  • the present invention is particularly directed to a liquid oral hygiene
  • composition with an improved minty flavor comprising (a) a flavor oil substantially free of undesirable
  • the present invention is directed to the liquid oral hygiene composition wherein the undesirable components comprising terpenes have been removed from the flavor oil by extraction or
  • the present invention is directed to the liquid oral hygiene composition wherein the terpenes are characterized by fractions of monoterpenes and sesquiterpenes.
  • the present invention is, moreover, directed to the liquid oral hygiene composition wherein the flavor oil is a mint oil.
  • the present invention is directed to the liquid oral hygiene composition wherein the mint oil is is derived from peppermint, spearmint, corn mint and mixtures thereof.
  • composition of the present invention wherein the mint oil is present in concentrations ranging from about 0.01% to about 5.0% by weight of the composition.
  • a liquid oral hygiene composition is directed to the present invention having a solution of a clarity of 5 National Turbidity Units (NTU) or less or, preferably, 3 NTU or less.
  • NTU National Turbidity Units
  • An embodiment of the liquid oral hygiene composition according to the present invention further includes an intense sweetening agent the concentration ranging up to about 3.0% by weight of the composition.
  • the intense sweetening agent is selected from the group consisting of sodium or calcium saccharin salts, the free acid form of saccharin, cyclamate salts, chlorosucrose derivatives, dipeptide compounds, acesulfame-K, and blends thereof.
  • An improved mint flavored clear mouthwash composition containing substantially terpene free peppermint oil, one or more surfactant components ranging from about 0.01% to about 3% by weight, ethyl alcohol ranging up to about 35% by weight, a sweetening agent ranging up to 3.0% by weight, an antimicrobial quaternary ammonium salt ranging from about 0.005% to about 5%, a fluorine providing compound ranging from about 0.001% to about 0.1%, a coloring agent, and a pharmaceutically acceptable buffer ranging from about 0.05% to about 0.5% by weight.
  • Oral composition as defined herein pertains to a product (final or intermediate) which is not necessarily intended to be ingested but to be retained in the oral cavity, especially near or on the teeth's surfaces for a time sufficient for full contact and oral activity.
  • Oral vehicle as defined herein pertains to food grade ingestible or pharmaceutically acceptable material, suitable for applying the inventive
  • composition in the oral cavity is a composition in the oral cavity.
  • Essential oils are volatile oils or essences derived from plants and usually carry the odor or flavor of the plant obtained by distillation, expression or extraction.
  • the essential flavorant oils of the present invention include, but are not limited to, thymol, spearmint oil, peppermint oil, lemon oil, orange oil, sage oil, rosemary oil, cinnamon oil, pimento oil, laurel oil, wintergreen oil, clove oil, and eucalyptus oil.
  • the clarity of appearance and cleaner taste of rectified essential oils and, in particular, mint oils in oral or dental hygiene compositions according to the present invention are discussed in greater detail below.
  • the oral composition includes an oral vehicle and is in the form of a liquid such as a
  • the concentration of the essential oil(s) ranges by weight from about 0.01% to about 1.0%.
  • Typical non-toxic oral carrier vehicles known in the field of dental care and hygiene may be used in the present invention.
  • Preferred oral vehicles include water and water-alcohol mixtures.
  • the water-alcohol mixtures are generally employed in a weight ratio from about 1:1 to about 20:1, preferably from about 3:1 to about 20:1, and most preferably from about 3:1 to about 10:1, respectively.
  • the pH value of the vehicle is generally from about 3.0 to about 8.5, and preferably from about 4 to about 4.5.
  • a vehicle having a pH value below about 3 is generally found as irritating to the oral cavity.
  • a vehicle having a pH value greater than about 8.5 generally results in an unpleasant mouth feel.
  • the preferred embodiments of liquid oral compositions, such as mouthwashes, rinses and other dentifrice of the present invention may contain
  • additives normally employed in liquid oral hygiene compositions include sorbitol solution, a surfactant, a fluorine providing compound, a sweetening agent, a flavoring agent, a coloring agent, a humectant, a buffer, and the like, providing the
  • additives do not interfere with the oral hygiene
  • composition of the present invention properties of the composition of the present invention.
  • the liquid oral clinically effective oral hygiene compositions of the present invention may contain sorbitol or sorbitol solution in high weight to volume concentrations (w/v), i.e., from about 10% to about 60%, and preferably from about 15% to about 40%, of sorbitol solution, U.S. Pharmacopeia, which is a solution of sorbitol in water containing 70% total solids. Sorbitol solution supplies sweetness and body to the composition and gives a desirable mouth feel.
  • w/v weight to volume concentrations
  • Sorbitol solution also enhances flavor, prevents harsh taste and provides a fresh and lively sensation in the mouth.
  • Surfactants are organic compounds which reduce surface tension between liquids and aid in the dispersion of a composition throughout the oral cavity.
  • the surfactant in the present invention may be nonionic, ampholytic, or cationic.
  • the liquid oral hygiene compositions of the present invention may contain surfactants in amounts up to about 5%, preferably from about 0.01% to about 3%, and more preferably from about 0.05% to about 2%, by weight of the liquid oral hygiene composition.
  • Suitable nonionic surfactants in the present invention include poly(oxyethylene)-poly(oxypropylene) block copolymers. Such copolymers are known
  • Poloxamers may have varying contents of ethylene oxide and propylene oxide which results in poloxamers which have a wide range of chemical
  • poloxamer surfactants of the present invention are non-toxic, are acceptable as direct food additives, are stable, readily dispersible in aqueous systems and are compatible with the wide variety of formulating
  • Poloxamer surfactants in the present invention should have a Hydrophilic-Lipophilic Balance (HLB) of between about 10 and about 30, and preferably between about 10 and about 25.
  • Suitable poloxamers in this invention include: Poloxamers 105, 108, 123, 124, 183, 184, 185, 188, 215, 217, 234, 235, 237, 238, 284, 288, 334, 335, 338, and 407.
  • HLB Hydrophilic-Lipophilic Balance
  • poloxamer is Poloxamer 407, which has an HLB of about 22, and is sold under the tradename Pluronic F-127 by BASF Wyandotte, Parsippany, N.J.
  • poloxamers should constitute from about 0.01% to about 5%, and preferably from about 0.05% to about 1%, by weight of the total volume of liquid oral hygiene composition (w/v).
  • nonionic surfactants useful in the oral composition of this invention are the ethoxylated hydrogenated castor oils. These surfactants are prepared by hydrogenating castor oil and treating the hydrogenated product with from about 10 to about 200 moles of ethylene glycol. These ethoxylated castor oils.
  • ethylene oxide added to the hydrogenated castor oil product Suitable PEG hydrogenated castor oils include PEG 16, 20, 25, 30, 40, 50, 60, 80, 100, and 200.
  • the PEG hydrogenated castor oil surfactant is Cremophor RH40, a commercially available product from BASF-Wyandotte, Parsippany, N.J. Ethoxylated hydrogenated castor oil surfactants, when present in the liquid oral dental hygiene composition for combatting plaque and
  • gingivitis should constitute from about 0.2% to about 2%, and preferably from about 0.5% to about 1%, by weight of the total volume of liquid oral hygiene composition (w/v).
  • nonionic surfactants useful in the present invention include condensates of sorbitan esters of fatty acids with ethylene oxide (polysorbates) such as sorbitan mono-oleate with from about 20 to about 60 mole percent of ethylene oxide (e.g., "Tween", a
  • Particularly preferred polysorbates are Polysorbate 20 (polyoxyethylene 20 sorbitan monolaurate, Tween 20) and Polysorbate 80
  • Additional suitable nonionic surfactants useful in the oral composition of the present invention are the condensation products of an alpha-olefin oxide containing 10 to 20 carbon atoms, a polyhydric alcohol containing 2 to 10 carbon atoms and 2 to 6 hydroxyl groups, and either ethylene oxide or a mixture of ethylene oxide and propylene oxide.
  • the resultant surfactants are polymers which have a molecular weight in the range from about 400 to about 1600, contain from about 40% to about 80% ethylene oxide, by weight, and have an alpha-olefin oxide to polyhydric alcohol mole ratio in the range from about 1:1 to about 1:3,
  • nonionic surfactants useful in the present invention include condensates of sorbitan esters of fatty acids with polyethylene glycol such as sorbitan diisostearate condensed with polyethylene glycol.
  • a particularly preferred polyethylene glycol condensate of a diisostearate sorbate ester is EmSorb 2726, a
  • Amphoteric surfactants have the capacity to behave as either an acid or a base.
  • surfactants useful in the present invention include quaternized imidazole derivatives.
  • Cationic surfactants are surfactants which carry a positive charge. Cationic surfactants
  • antimicrobial quaternary ammonium salts especially useful in the present invention include antimicrobial quaternary ammonium salts.
  • This class of compounds can be illustrated but not limited to,
  • cetylpyridinium chloride cetylpyridinium chloride, benzalkonium chloride,
  • a preferred embodiment of the present invention provides antimicrobial activity, domiphen bromide, 1-(3-chlorallyl)-3,5-7-triaza-1-azoniaadamantane chloride, and menthene ammonium chloride.
  • a preferred embodiment of the present invention provides antimicrobial activity, domiphen bromide, 1-(3-chlorallyl)-3,5-7-triaza-1-azoniaadamantane chloride, and menthene ammonium chloride.
  • quaternary ammonium salt detergent ranging from about 0.005% to about 5%.
  • Fluorine providing compounds may be fully or slightly water soluble and are characterized by their ability to release fluoride ions or fluoride containing ions in water and by their lack of reaction with other components in the composition. Typical fluorine
  • inorganic fluoride salts such as water-soluble alkali metal, alkaline earth metal, and heavy metal salts, for example, sodium fluoride,
  • potassium fluoride ammonium fluoride, cuprous fluoride, zinc fluoride, stannic fluoride, stannous fluoride, barium fluoride, sodium fluorosilicate, ammonium
  • the amount of fluorine providing compound present in a preferred embodiment of the liquid oral hygiene composition is dependent upon the type of fluorine providing compound employed, the solubility of the fluorine compound, and the nature of the final liquid oral hygiene composition.
  • the amount of fluorine providing compound used must be a nontoxic amount. In general, the fluorine providing compound when used will be present in an amount up to about 1%, preferably from about 0.001% to about 0.1%, and most preferably from about 0.001% to about 0.05%, by weight of the liquid oral hygiene composition.
  • sweetening agents those sweeteners well-known in the art, including both natural and artificial sweeteners, may be employed.
  • the sweetening agent used may be selected from a wide range of materials including water-soluble sweetening agents. water-soluble artificial sweetening agents,
  • water-soluble sweetening agents derived from naturally occurring water-soluble sweetening agents, dipeptide based sweetening agents, and protein based sweetening agents, including mixtures thereof.
  • representative categories and examples include:
  • water-soluble sweetening agents such as monosaccharides, disaccharides and polysaccharides such as xylose, ribose, glucose (dextrose), mannose,
  • galactose fructose (levulose), sucrose (sugar), maltose, invert sugar (a mixture of fructose and glucose derived from sucrose), partially hydrolyzed starch, corn syrup solids, dihydrochalcones, monellin, steviosides, glycyrrhizin, and sugar alcohols such as sorbitol, mannitol, maltitol, hydrogenated starch hydrolysates and mixtures thereof;
  • water-soluble artificial sweeteners such as soluble saccharin salts, i.e., sodium or calcium saccharin salts, cyclamate salts, the sodium, ammonium or calcium salt of 3,4-dihydro-6-methyl -1,2,3-oxathiazine-4-one-2, 2-dioxide, the potassium salt of 3,4-dihydro-6-methyl - 1,2,3-oxathiazine-4-one-2, 2-dioxide (Acesulfame-K), the free acid form of
  • L-aspartic acid derived sweeteners such as
  • water-soluble sweeteners derived from naturally occurring water-soluble sweeteners such as chlorinated derivatives of ordinary sugar (sucrose), known, for example, under the product designation of Sucralose;
  • an effective amount of sweetening agent is utilized to provide the level of sweetness desired in any particular liquid oral hygiene
  • compositions and this amount will vary with the
  • sweetener selected and the final liquid oral hygiene product The amount of sweetener normally present is in the range from about 0.0025% to about 90%, by weight of the embodiment of the liquid oral hygiene composition such as mouthwash or rinse, depending upon the sweetener used. The exact range of amounts for each type of sweetener is well known in the art and is not the subject of the present invention.
  • the flavoring agents include those flavors known to the skilled artisan, such as natural and artificial flavors. Suitable flavoring agents include mints, such as peppermint, citrus flavors such as orange and lemon, artificial vanilla, cinnamon, various fruit flavors, both individual and mixed and the like.
  • the amount of flavoring agent employed herein is normally a matter of preference subject to such factors as the type of final liquid oral hygiene
  • composition the individual flavor and the strength of flavor desired.
  • amount of flavoring may be varied in order to obtain the result desired in the final product and such variations are within the
  • flavoring agents when used, are generally utilized in amounts that may, for example, range in amounts from about 0.05% to about 6%, by weight of the liquid oral hygiene composition.
  • the coloring agents (colors, colorants) useful in the present invention are used in amounts effective to produce the desired color.
  • the colorants may include natural food colors and dyes suitable for food, drug and cosmetic applications. These colorants are known as F. D. & C dyes and lakes.
  • the materials acceptable for the foregoing uses are preferably water-soluble.
  • Illustrative nonlimiting examples include the indigoid dye known as F. D. & C Blue No.2, which is the disodium salt of 5,5-indigotindisulfonic acid.
  • the dye known as F. D. & C Green No.1 comprises a triphenylmethane dye and is the monosodium salt of 4-[4-(N-ethyl-p-sulfoniumbenzylamino)
  • Suitable humectants in the oral composition of the present invention include glycerin, propylene glycol, polyethylene glycol, sorbitan, fructose,
  • employed, may be present in amounts from about 10% to about 60%, by weight of the liquid oral hygiene
  • Suitable buffers in the present invention include citric acid-sodium citrate, phosphoric
  • an oral antiseptic composition according to the present invention is made by first dissolving the surfactant, cetylpyridinium chloride, in water, then admixing sorbitol or sorbitol solution to the surfactant solution until the sorbitol is dissolved. Coloring agents, additional sweetening agents, and similar additives are admixed at the same time sorbitol is added. Flavorants, such as peppermint oil,
  • eucalyptol, and thymol are then admixed to the surfactant/sorbitol solution until dissolved.
  • the pH value of the solution is adjusted to 4-6 using 1-N hydrochloric acid or 1-N sodium hydroxide. Then
  • peppermint oil, eucalyptol, and thymol are conveniently added to the solution in the alcohol portion if any.
  • the apparatus useful in accordance with the present invention comprises mixing apparatus well known in the dental art, and therefore the selection of the specific apparatus will be apparent to the artisan.
  • Mint oils (from the Greek Mintho) are well known throughout the ages and originated in the
  • mint oils are extracted mainly from the leaf of mint plants. Its yield varies from one growing region to another. For the purpose of uniformity and consistency as well as purity or lack of contaminant toxic substances,
  • Table I shows an comparative analysis of peppermint oils from several different sources by gas chromatography.
  • Table II shows similarly obtained chromatographic data of spearmint oil constituents from four sources.
  • An important aspect of the present invention is the special fractionation of the oils to improve quality. This method achieves other special benefits as well as, e.g., enhanced flavor penetration or
  • the flavor oil that is incorporated into the oral hygiene composition has been fractionated or rectified using standard distillation equipment to remove the terpene components that act as flavor
  • Monoterpenes (II) are basically comprised of two of the above isoprene units whereas sesquiterpenes (III) are comprised of three of these units.
  • Standard deterpenation which results in removal of most of the "head” (monoterpene) fraction from the essential oil is also beneficial in providing enhanced flavor perception the fractionation of the oil is removing the "head” as well as the "tail” fractions.
  • Flavoring oils of particular utility in the practice of the present invention are those of the mint variety (Genus Mentha) such as peppermint (Mentha).
  • cinnamon is grown in China, Japan and South America and not considered “peppermint" in the U.S.A..
  • the amount of deterpenated flavor oil employed is normally a matter of preference but it has been found that amounts ranging from approximately 0.01% to approximately 5.0% by weight of the final composition are usable with amounts of about 0.1% to about 3% by weight being preferred.
  • the mint oils of the present invention can be utilized as the sole flavorant or can be combined with other standard single distillation mint oils.
  • Highly rectified peppermint oils and highly rectified deterpenated peppermint oils were compared in certain preferred embodiments of the mouthwashes in accordance with the present invention.
  • the highly rectified deterpenated oils were devoid of monoterpene fractions as the so-called "heads” fraction and the major portion of the so-called “tails” fraction comprising sesquiterpene compounds and derivatives thereof.
  • Highly rectified peppermint oils which are only about 50% relieved of the head monoterpene
  • peppermint oils are the prime quality Madras product from the Madras region in Oregon (U.S.A.), Rose Mitcham, rectified oil from a blend of Farwest Williamette, Midwest and Madras, and Farwest Terpeneless VR, a heavy fractionation of a blend of prime quality natural peppermint oils from the Madras Williamette Farwest producing regions of the U.S.A.
  • This product is steam distilled from fresh overground parts of the flowering plant, Mentha Piperata L.
  • the Farwest terpeneless oil is produced by the procedure essential oils, as e.g., similar to the rectification of lemon oil disclosed in U.S. Patent 3,867,262 as incorporated by reference, for illustration purposes:
  • the distillation residue (0.9 g.) consisted largely of high boiling waxes, coumarins, and
  • Chromatographic grade neutral alumina 60 g. was added to 100 ml. of ethyl acetate and the mixture was stirred gently. The alumina was allowed to settle and excess ethyl acetate was removed by decantation. The remaining alumina-ethyl acetate slurry was dried in a shallow layer for 16 hours at 70° F., after which time the odor of the ethyl acetate was only barely
  • the airdried alumina was added to a Kontes Chromaflex No. 25 glass-jacketed chromatographic column containing commercial pentane, which had been cooled and held at 10° C. by circulating cold water through the outer column jacket.
  • the alumina was allowed to settle evenly, aided by occasional gentle tapping of the column. Excess pentane was drained through the column until a "head" of one-sixteenth inch of pentane remained over the flat alumina surface at the top of the column.
  • the distillate from Part A (23.5 ml.) was carefully layered onto the surface of the alumina column prepared in Part B.
  • the effluent stopcock was opened slightly and the distillate allowed to percolate into the alumina bed until level with the tope of the alumina adsorbent.
  • Commercial pentane was carefully added to the column without disturbing the surface layer.
  • the effluent stopcock was opened and the pentane allowed to flow freely through the column.
  • Approximately 115 ml. of effluent was obtained before a change in refraction occurred, indicating initial elution of the terpene hydrocarbons.
  • the next 60 ml. of effluent contained all the terpenes. This eluate was collected, and the terpenes were recovered by low-temperature distillation to remove the pentane. Analysis of this fraction indicated that essentially no oxygenated compounds were present.
  • the pentane head on the alumina column (from Part C) was allowed to recede to within one-sixteenth inch of the surface of the alumina and 120 ml. of absolute ethanol was placed carefully on the column. The first 45 ml. of eluate was essentially pure pentane that had occupied the liquid portion of the column prior to addition of the ethanol. A clear change in
  • a sample of the product was dissolved in ethanol and it was found that this solution was entirely miscible with water.
  • Aqueous solutions for example, of the ethanolic, terpeneless lemon oil retained their typical lemon flavor during storage in green-colored Pyrex, screw-capped (Teflon liners), bottled at ambient temperature for at least one year without loss in flavor or development of off-flavor.
  • similar solutions of whole lemon oil developed off-flavors and odors within a few weeks.
  • fractionated peppermint oil containing lower amounts of menthone This particularly desirable, rectified peppermint oil has very low "head” and “tail” fractions as well as reduced concentrations of other components such as, e.g., 3-octanol, 1-octen-3-ol, menthofuran, and iso-menthone (see Table III). All percentages throughout the specification are by weight percent of the final composition unless otherwise specified.
  • Preparation A was undertaken to determine the turbidity readings on the following basic liquid oral composition type mouthrinse product flavored with different types of peppermint oil.
  • PROCEDURE
  • step (3) Slowly add step (1) to step (2) while mixing rapidly;
  • the turbidity measurement are indicate a marked improvement due to the highly rectified
  • Glycerin sodium saccharin, citric acid, sodium cetrate, sodium lauryl sulfate, yellow #10, green #3, poloxamer 407 (Part 1).
  • ingredients such as may be present in the composition of a mouthwash (See TABLE V) and may shorten shelf-life.

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Abstract

Composition liquide d'hygiène orale contenant une huile d'aromatisation spécialement rectifiée telle qu'une huile de pepppermint afin d'obtenir un goût pur moins amer, et réduisant la présence de menthol et de tensioactif. Les huiles de peppermint traitées par rectification spéciale présentent un effet avantageux sur l'efficacité et l'arôme de produits d'hygiène orale contenant de plus faibles quantités d'alcool.
PCT/US1994/005118 1993-05-20 1994-05-09 Arome peppermint ameliore pour produits d'hygiene orale WO1994027566A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU68285/94A AU6828594A (en) 1993-05-20 1994-05-09 Improved peppermint flavor for oral hygiene products

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US6520593A 1993-05-20 1993-05-20
US08/065,205 1993-05-20

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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997030685A1 (fr) * 1996-02-23 1997-08-28 Warner-Lambert Company Bain de bouche a teneur alcoolique reduite
US5681549A (en) * 1994-06-10 1997-10-28 The Procter & Gamble Company Mouthrinse compositions
US6548085B1 (en) * 1998-04-15 2003-04-15 Woodstream Corporation Insecticidal compositions and method of controlling insect pests using same
WO2008005549A3 (fr) * 2006-07-07 2008-06-26 Procter & Gamble Huiles aromatisantes à teneur réduite en soufre et utilisation dans des compositions d'hygiène bucco-dentaire
US8283135B2 (en) 2000-06-30 2012-10-09 The Procter & Gamble Company Oral care compositions containing combinations of anti-bacterial and host-response modulating agents
US9155769B2 (en) 2006-07-07 2015-10-13 The Procter & Gamble Co Flavor oils with reduced dimethyl sulfoxide content and use in oral compositions
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US11351097B2 (en) * 2015-12-30 2022-06-07 Colgate-Palmolive Company Oral care product and methods of use and manufacture thereof

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US5681549A (en) * 1994-06-10 1997-10-28 The Procter & Gamble Company Mouthrinse compositions
US5686063A (en) * 1994-06-10 1997-11-11 The Procter & Gamble Company Mouthrinse compositions
WO1997030685A1 (fr) * 1996-02-23 1997-08-28 Warner-Lambert Company Bain de bouche a teneur alcoolique reduite
US6548085B1 (en) * 1998-04-15 2003-04-15 Woodstream Corporation Insecticidal compositions and method of controlling insect pests using same
US8283135B2 (en) 2000-06-30 2012-10-09 The Procter & Gamble Company Oral care compositions containing combinations of anti-bacterial and host-response modulating agents
US9241885B2 (en) 2004-01-29 2016-01-26 The Procter & Gamble Company Oral care compositions comprising increased bioavailable levels of quaternary ammonium antimicrobials
WO2008005549A3 (fr) * 2006-07-07 2008-06-26 Procter & Gamble Huiles aromatisantes à teneur réduite en soufre et utilisation dans des compositions d'hygiène bucco-dentaire
US8007771B2 (en) 2006-07-07 2011-08-30 The Procter & Gamble Company Flavors for oral compositions
US8865192B2 (en) 2006-07-07 2014-10-21 The Procter & Gamble Co Flavor oils with reduced sulfur content and use in oral care compositions
US9155769B2 (en) 2006-07-07 2015-10-13 The Procter & Gamble Co Flavor oils with reduced dimethyl sulfoxide content and use in oral compositions
US11351097B2 (en) * 2015-12-30 2022-06-07 Colgate-Palmolive Company Oral care product and methods of use and manufacture thereof

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