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WO1997030685A1 - Bain de bouche a teneur alcoolique reduite - Google Patents

Bain de bouche a teneur alcoolique reduite Download PDF

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Publication number
WO1997030685A1
WO1997030685A1 PCT/US1996/002480 US9602480W WO9730685A1 WO 1997030685 A1 WO1997030685 A1 WO 1997030685A1 US 9602480 W US9602480 W US 9602480W WO 9730685 A1 WO9730685 A1 WO 9730685A1
Authority
WO
WIPO (PCT)
Prior art keywords
composition
reduced alcohol
reduced
mouthwash composition
antimicrobial mouthwash
Prior art date
Application number
PCT/US1996/002480
Other languages
English (en)
Inventor
Pauline Pan
R. Michael Buch
Frank Volpe
Michael Rubin
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 PCT/US1996/002480 priority Critical patent/WO1997030685A1/fr
Priority to AU53552/96A priority patent/AU5355296A/en
Publication of WO1997030685A1 publication Critical patent/WO1997030685A1/fr

Links

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
    • 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
    • A61K8/347—Phenols
    • 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
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
    • 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

Definitions

  • Listerine ® -brand mouthwash is a well-known antiseptic mouthwash that has been used by millions of people for over one hundred years and has been proven effective in killing microbes in the oral cavity that are responsible for plaque, gingivitis and bad breath.
  • Thymol together with other essential oils such as methyl salicylate, menthol and eucalyptol, are active ingredients in antiseptic mouth rinses such as Listerine ® . These oils achieve their efficacy although present in small amounts. Without being restricted to any specific theory, it is now believed that the efficacy and taste of antiseptic mouthwashes such as Listerine ® may be due to the dissolution of these four active ingredients.
  • the amount of polyols employed is generally inversely proportional to the amount of ethanol; that is, as the level of ethanol is reduced below about 22% v/v, it is generally necessary to increase the concentration of polyols beyond about 18% w/v to maintain good antimicrobial efficacy.
  • a reduced alcohol, antimicrobial mouthwash composition which comprises (a) an antimicrobially effective amount of one or more essential oils; (b) a reduced level, up to about 22% v/v, of ethanol; (c) at least about 18% w/v of one or more polyols sufficient to provide an enhanced antimicrobial activity of said essential oils at said reduced level of ethanol, such that the R-Factor (defined below) of said mouthwash composition is less than about 2.0, preferably less than about 1.2, and most preferably less than about 1.0; and (d) water.
  • reduced level of alcohol is meant an amount of ethanol up to about 22% v/v, such as an amount of from about 9% v/v to about 22% v/v,
  • the ratio of water to ethanol is in the range of from about 3:1 to about 25:1, preferably from about 3.2:1 to about 10:1, by volume.
  • Suitable flavors include oil of anise (about 0.01% w/v to about 0.2% w/v) and benzyl alcohol (about 0.001% w/v to about 0.1% w/v).
  • the mouthwash is a clear, green color and further includes spearmint oil (about 0.01% w/v to about 2.0% w/v) as an additional flavorant.
  • spearmint oil about 0.01% w/v to about 2.0% w/v
  • Other flavors such as citrus oils, vanillin and the like may be incorporated to provide further taste variations.
  • a mouthwash composition that is totally free of anethole or at least essentially free of anethole (i.e., trace amounts or amounts which are so small as to not contribute functionally to the taste or flavor properties of the composition).
  • the particular flavor oils and other taste-improving ingredients employed will vary depending upon the particular taste and feel desired. Those skilled in the art can select and customize these types of ingredients to provide the desired results.
  • Zinc chloride may be added as an astringent for an "antiseptic cleaning" feeling in an amount of from about 0.0025% w/v to about 0.0075% w/v.
  • the mouthwash formulations of the present invention may be formulated to be substantially clear and colorless, acceptably approved food dyes are preferably used to provide a pleasing color to the formulations of the invention. These may be selected from the long list of acceptable food dyes and in particular may be
  • the mouthwash composition of the present invention may also be formulated, if desired, as gels, foams, pastes,
  • the mouthwash compositions of the present invention may be formulated in a dry powder, chewing gum, semi-solid, solid or liquid concentrate form.
  • water is added to q.s. the volume to the necessary total for a liquid concentrate, or water may be removed using standard evaporation procedures known in the art to prepare a composition in dry powder form. Both may then have water added at a later date when ready for use.
  • Such forms are advantageous for storage and shipping.
  • Jordan's medium with pH indicator (“recovery medium”) is prepared by adding 1 ml of a 1% bromocresol purple stock solution (i.e., 0.1 gram bromocresol purple in 10 mis distilled water) to 1 liter of
  • the culture for the assay is prepared as follows. Upon receipt, the ATCC culture is rehydrated and subcultured according to the directions supplied by the American Type Culture Collection. The subculture is streaked for purity on Brain-Heart Infusion Agar (DIFCO) and inoculated into 100 ml of sterile BHI. The agar plates are examined for purity after 14-18 hours. If
  • test tubes are then incubated anaerobically overnight (i.e., 14-16 hours) at 37°C.
  • the number of test tubes will vary depending upon the number of different mouthwash samples being tested, but it will be convenient to describe an assay of a
  • mouthwash with the succeeding four sets of three tubes each in that row being reserved for the four reduced alcohol samples. There are three tubes in each set because each assay is performed in triplicate.
  • plaque wires are then transferred into fresh Jordan's medium in 75 tubes (in a second rack) and again incubated anaerobically for 24 hours at 37°C. This procedure is repeated once more.
  • the plaque wires are cultured for 3 days, with two transfers after initial inoculation.
  • additional racks are prepared: a first (assay) rack whose test tubes each contain 6 ml of the sample mouthwashes; a second (water) rack whose test tubes each contain 6 ml of sterile deionized water; third and fourth racks whose test tubes each contain 6 ml of Letheen broth rinse; and a fifth rack whose test tubes each contain 5 ml of Jordan's recovery medium.
  • the racks may be marked for test series identity and time (by row).
  • Assay Procedure Each assay will involve triplicate testing at time points separated by one minute
  • intervals e.g., at 2, 3, 4, 5 and 6 minutes of
  • the exact time of exposure of the plaque wires to the sample mouthwashes can be varied according to the thickness of the "plaques;” ideally, the exposure period will result in positive microorganism growth in the first one or two sampling intervals of the high alcohol control group, (i.e., the first and second row) and no growth thereafter.
  • Mouthwash exposure takes place in a 37° New Brunswick shaking water bath (shake speed 3) and may be staggered so that the 5 time points are run concurrently, but with sufficient time to permit accurate timing and handling.
  • Positive growth is indicated by a color change from purple to yellow (i.e., if the microorganism is still viable, it will produce an acid which causes the color change); positive growth is often accompanied by an increase in broth turbidity.
  • each mouthwash sample is located in the same set of three tubes in each row of the rack, the critical time necessary for the sample to completely kill the microorganism can be determined by observing the point (front to back or bottom to top, as the case may be) at which the Jordan recovery medium color changed from yellow to purple.
  • the critical kill time for any sample divided by the critical kill time for the control mouthwash in that same rack, gives the R-Factor for that sample.
  • Table 2 summarizes a statistical scale developed by the present inventors which relates the observed change from growth (+) to no growth (-) to critical kill times. For example, as shown in the first row of Table 2, where the observed condition changes from growth (continuous +'s) to no growth (continuous -'s) ("no anomaly"), the critical kill time is determined by adding 0.50 minute to the time at which the last growth observation (+) was made. The balance of Table 2 sets forth how critical kill times are determined for different observed growth/no growth intervals between continuous growth segments and continuous no growth segments.
  • a mouthwash composition containing 19% v/v ethanol and 18% w/v sorbitol was prepared as follows. First, an alcohol solution of active essential oils and flavor oils was prepared by dissolving the ingredients listed in Table 4 in 200 mls of ethanol (USP): To the resulting alcohol solution were then added the additional ingredients shown in Table 5 (along with suitable dyes to obtain the desired color):
  • the pH was adjusted to 4.2. Approximately 600 mls of deionized water was then added, and the solution was mixed until all solids were dissolved. Additional deionized water was added with mixing to bring the total solution to 1 liter. A clear mouthwash solution was obtained.
  • Example 2 A number of different mouthwash compositions A-J were prepared. The composition ingredients and amounts used (except for the dyes) are shown in Table 6 below.
  • the mouthwashes were prepared as follows. An alcohol solution was prepared by dissolving the flavor oils, part of the thymol and part of the methyl salicylate in 227 or 200 milliters of ethanol (USP). Into the resulting solution was then dissolved the remaining methyl salicylate, the remaining thymol, the benzoic acid and the Pluronic surfactant. 300 mis of the deionized water was then slowly added to the resulting solution, with mixing. The sorbitol (USP) solution, or propylene glycol, was then added, with continued mixing, followed by the sodium saccharin, the sodium citrate and the citric acid, with mixing until
  • Endotoxin is a component of the outer wall of Gram negative bacteria and if shed by the bacteria at or near infection sites about the teeth and gums will elicit inflammation and gingivitis. Removal of
  • Control mouthwash was the high alcohol (27% v/v) standard described above.
  • mouthwash clearly decrease the degree of endotoxin remaining in the culture, supporting its value in preventing inflammation and subsequent gum disease.
  • plaque penetration assay (described above) -- was employed in this invention.
  • the results of this assay reported as "Critical Kill Times" (or "CKT"), are more predictive of the in vivo effect of oral mouthrinses than endotoxin measurements.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Emergency Medicine (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Cosmetics (AREA)

Abstract

L'invention a trait à une composition antimicrobienne pour bains de bouche, efficace pour prévenir et atténuer la mauvaise haleine, la plaque dentaire et les affections gingivales connexes, comportant une quantité efficace sur le plan antimicrobien d'une ou de plusieurs huiles essentielles actives, une concentration réduite, allant jusqu'à 22 % en poids volume, d'alcool, des concentrations renforcées, d'au moins 18 % en poids volume d'un ou de plusieurs polyols augmentant l'efficacité des substances actives dans la cavité buccale et de l'eau. Ces substances actives non seulement renforcent l'efficacité du produit mais sont, de surcroît, entièrement dissoutes dans de faibles concentrations d'éthanol, ce qui donne au produit un aspect attrayant.
PCT/US1996/002480 1996-02-23 1996-02-23 Bain de bouche a teneur alcoolique reduite WO1997030685A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
PCT/US1996/002480 WO1997030685A1 (fr) 1996-02-23 1996-02-23 Bain de bouche a teneur alcoolique reduite
AU53552/96A AU5355296A (en) 1996-02-23 1996-02-23 Reduced alcohol mouthwash

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/US1996/002480 WO1997030685A1 (fr) 1996-02-23 1996-02-23 Bain de bouche a teneur alcoolique reduite

Publications (1)

Publication Number Publication Date
WO1997030685A1 true WO1997030685A1 (fr) 1997-08-28

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AU (1) AU5355296A (fr)
WO (1) WO1997030685A1 (fr)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6261540B1 (en) * 1997-10-22 2001-07-17 Warner-Lambert Company Cyclodextrins and hydrogen peroxide in dental products
US6348187B1 (en) * 1996-01-24 2002-02-19 Warner-Lambert Company Peroxide/essential oils containing mouthwash compositions and two-part mouthwash systems
FR2905065A1 (fr) * 2006-08-24 2008-02-29 Tonino Vilia Composition cosmetique universelle aromatique a pouvoir regenerant pour le bien etre du corps
US7601731B2 (en) * 2003-06-06 2009-10-13 Board Of Regents, The University Of Texas System Antimicrobial flush solutions
EP1774953A3 (fr) * 2005-10-17 2010-01-20 Henkel AG & Co. KGaA Collutoire concentré
EP1774955A3 (fr) * 2005-10-17 2010-02-17 Henkel AG & Co. KGaA Collutoire prêt-à-l'emploi
US20120003163A1 (en) * 2010-06-30 2012-01-05 Mcneil-Ppc, Inc. Non-Alchohol Bioactive Essential Oil Mouth Rinses
CN102309424A (zh) * 2010-06-30 2012-01-11 麦克内尔-Ppc股份有限公司 制备无醇生物活性精油漱口液的方法
WO2022109261A3 (fr) * 2020-11-20 2022-07-21 Howard Frysh Élimination de tartre dentaire
CN119678946A (zh) * 2025-02-21 2025-03-25 温州医科大学附属第一医院 采用saew协同百里酚的抗菌消毒方法及其产品

Citations (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3250681A (en) * 1961-12-04 1966-05-10 Celanese Corp Ethylidene diacetate as bacteriostat in cosmetic and other compositions
EP0338978A2 (fr) * 1988-03-31 1989-10-25 Warner-Lambert Company Masquage du goût du thymol
EP0373758A2 (fr) * 1988-12-14 1990-06-20 Warner-Lambert Company Compositions antiseptiques contenant des dérivés de la hexahydro-5-pyrimidine-amine et du thymol et leur procédé de préparation
EP0497476A2 (fr) * 1991-01-30 1992-08-05 Colgate-Palmolive Company Compositions orales antiplaques
WO1994007477A1 (fr) * 1992-10-07 1994-04-14 Warner-Lambert Company Masquage du gout du thymol
WO1994018939A1 (fr) * 1993-02-19 1994-09-01 Warner-Lambert Company Composition de rinçage utilisee avant le brossage
WO1994027566A1 (fr) * 1993-05-20 1994-12-08 Warner-Lambert Company Arome peppermint ameliore pour produits d'hygiene orale
DE4418796A1 (de) * 1993-06-02 1994-12-15 Colgate Palmolive Co Oral anwendbare und gegen Plaque und Gingivitis wirkende Zusammensetzungen
WO1995034276A1 (fr) * 1994-06-10 1995-12-21 The Procter & Gamble Company Compositions de bain de bouche
EP0692246A1 (fr) * 1994-07-15 1996-01-17 Colgate-Palmolive Company Compositions orales
WO1996015770A1 (fr) * 1994-11-17 1996-05-30 Warner-Lambert Company Compositions antimicrobiennes orales
WO1996016633A1 (fr) * 1994-12-02 1996-06-06 Warner-Lambert Company Bain de bouche a teneur reduite en alcool

Patent Citations (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3250681A (en) * 1961-12-04 1966-05-10 Celanese Corp Ethylidene diacetate as bacteriostat in cosmetic and other compositions
EP0338978A2 (fr) * 1988-03-31 1989-10-25 Warner-Lambert Company Masquage du goût du thymol
US4945087A (en) * 1988-03-31 1990-07-31 Warner-Lambert Company Taste masking of thymol
EP0373758A2 (fr) * 1988-12-14 1990-06-20 Warner-Lambert Company Compositions antiseptiques contenant des dérivés de la hexahydro-5-pyrimidine-amine et du thymol et leur procédé de préparation
EP0497476A2 (fr) * 1991-01-30 1992-08-05 Colgate-Palmolive Company Compositions orales antiplaques
WO1994007477A1 (fr) * 1992-10-07 1994-04-14 Warner-Lambert Company Masquage du gout du thymol
WO1994018939A1 (fr) * 1993-02-19 1994-09-01 Warner-Lambert Company Composition de rinçage utilisee avant le brossage
WO1994027566A1 (fr) * 1993-05-20 1994-12-08 Warner-Lambert Company Arome peppermint ameliore pour produits d'hygiene orale
DE4418796A1 (de) * 1993-06-02 1994-12-15 Colgate Palmolive Co Oral anwendbare und gegen Plaque und Gingivitis wirkende Zusammensetzungen
WO1995034276A1 (fr) * 1994-06-10 1995-12-21 The Procter & Gamble Company Compositions de bain de bouche
EP0692246A1 (fr) * 1994-07-15 1996-01-17 Colgate-Palmolive Company Compositions orales
WO1996015770A1 (fr) * 1994-11-17 1996-05-30 Warner-Lambert Company Compositions antimicrobiennes orales
WO1996016633A1 (fr) * 1994-12-02 1996-06-06 Warner-Lambert Company Bain de bouche a teneur reduite en alcool

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6348187B1 (en) * 1996-01-24 2002-02-19 Warner-Lambert Company Peroxide/essential oils containing mouthwash compositions and two-part mouthwash systems
US6261540B1 (en) * 1997-10-22 2001-07-17 Warner-Lambert Company Cyclodextrins and hydrogen peroxide in dental products
US8709342B2 (en) 2003-06-06 2014-04-29 Board Of Regents, The University Of Texas System Antimicrobial flush solutions
US9078441B2 (en) 2003-06-06 2015-07-14 Board Of Regents, The University Of Texas System Antimicrobial flush solutions
US7601731B2 (en) * 2003-06-06 2009-10-13 Board Of Regents, The University Of Texas System Antimicrobial flush solutions
EP1774953A3 (fr) * 2005-10-17 2010-01-20 Henkel AG & Co. KGaA Collutoire concentré
EP1774955A3 (fr) * 2005-10-17 2010-02-17 Henkel AG & Co. KGaA Collutoire prêt-à-l'emploi
FR2905065A1 (fr) * 2006-08-24 2008-02-29 Tonino Vilia Composition cosmetique universelle aromatique a pouvoir regenerant pour le bien etre du corps
US20120003163A1 (en) * 2010-06-30 2012-01-05 Mcneil-Ppc, Inc. Non-Alchohol Bioactive Essential Oil Mouth Rinses
CN102309424A (zh) * 2010-06-30 2012-01-11 麦克内尔-Ppc股份有限公司 制备无醇生物活性精油漱口液的方法
US20140322146A1 (en) * 2010-06-30 2014-10-30 Mcneil-Ppc, Inc. Methods of preparing non-alcohol bioactive essential oil mouth rinses
US9084902B2 (en) 2010-06-30 2015-07-21 Mcneil-Ppc, Inc. Non-alchohol bioactive essential oil mouth rinses
US9693944B2 (en) 2010-06-30 2017-07-04 Johnson & Johnson Consumer Inc. Methods of preparing non-alcohol bioactive essential oil mouth rinses
US9763863B2 (en) 2010-06-30 2017-09-19 Johnson & Johnson Consumer Inc. Methods of preparing non-alcohol bioactive essential oil mouth rinses
US10434050B2 (en) 2010-06-30 2019-10-08 Johnson & Johnson Consumer Inc. Methods of preparing non-alcohol bioactive essential oil mouth rinses
US10993894B2 (en) 2010-06-30 2021-05-04 Johnson & Johnson Consumer Inc. Methods of preparing non-alcohol bioactive essential oil mouth rinses
WO2022109261A3 (fr) * 2020-11-20 2022-07-21 Howard Frysh Élimination de tartre dentaire
CN119678946A (zh) * 2025-02-21 2025-03-25 温州医科大学附属第一医院 采用saew协同百里酚的抗菌消毒方法及其产品

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