WO2011053877A2 - Compositions oxydantes à haute stabilité - Google Patents

Compositions oxydantes à haute stabilité Download PDF

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Publication number
WO2011053877A2
WO2011053877A2 PCT/US2010/054873 US2010054873W WO2011053877A2 WO 2011053877 A2 WO2011053877 A2 WO 2011053877A2 US 2010054873 W US2010054873 W US 2010054873W WO 2011053877 A2 WO2011053877 A2 WO 2011053877A2
Authority
WO
WIPO (PCT)
Prior art keywords
whitening
teeth
whitening composition
composition
hydrogen peroxide
Prior art date
Application number
PCT/US2010/054873
Other languages
English (en)
Other versions
WO2011053877A3 (fr
Inventor
R. Eric Montgomery
Original Assignee
Discus Dental, Llc
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 Discus Dental, Llc filed Critical Discus Dental, Llc
Publication of WO2011053877A2 publication Critical patent/WO2011053877A2/fr
Publication of WO2011053877A3 publication Critical patent/WO2011053877A3/fr

Links

Classifications

    • 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
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/22—Peroxides; Oxygen; Ozone
    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A61K8/8158—Homopolymers or copolymers of amides or imides, e.g. (meth) acrylamide; Compositions of derivatives of such polymers
    • 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
    • A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
    • A61K2800/87—Application Devices; Containers; Packaging

Definitions

  • the present invention relates to compositions used to whiten teeth, and more particularly to highly stable oxidizing compositions comprising hydrogen peroxide and an oxidation-resistant thickened carrier comprising a 2-acrylamido-2-methylpropane sulfonic acid (AMPS) polymer or copolymer.
  • AMPS 2-acrylamido-2-methylpropane sulfonic acid
  • the inventive compositions thickened with an AMPS polymer or copolymer are found to be unexpectedly stable, particularly with respect to viscosity and hydrogen peroxide concentration over time, such that highly effective tooth whitening gels may be formulated and stored at room temperature for extended periods of time without the need for refrigeration.
  • hydrogen peroxide is formulated into gel or paste compositions that have sufficient "body” (or in other words, a high enough level of viscosity and/or thixotropy) in order to adhere, cling or otherwise remain in contact with the tooth surfaces without risk of migrating to adjacent soft tissue surfaces such as the crevicular spaces, the lingual and buccal mucosa, and other soft tissue surfaces in the oral cavity.
  • Body or in other words, a high enough level of viscosity and/or thixotropy
  • Whitening compositions with sufficient body are also easier to apply using standard clinical applicators such as brushes, syringes, swabs and other similar devices.
  • Polymers and copolymers such as carboxypolymethylene (Carbopol®), acrylic acid / C10-C30 alkyl acrylate copolymers (Pemulen®), polyoxyethylene / polyoxypropylene block copolymers (Pluronic®), and hydroxypropylcellulose (Klucel®), amongst others, have been used with varying degrees of success, but generally exhibiting a time- and temperature- dependent decrease in viscosity in the presence of hydrogen peroxide and even when composition stabilizers are present.
  • Polymers and copolymers such as carboxypolymethylene (Carbopol®), acrylic acid / C10-C30 alkyl acrylate copolymers (Pemulen®), polyoxyethylene / polyoxypropylene block copolymers (Pluronic®), and hydroxypropylcellulose (Klucel®), amongst others, have been used with varying degrees of success, but generally exhibiting a time- and temperature- dependent decrease in viscosity
  • polymers and copolymers utilized in the present inventive compositions may be employed for their particularly unique properties, such as reduced water solubility for those circumstances in which long term gel contact could lead to "leaching" of a typical water-soluble gel from a delivery device such as a dental tray. Such leaching can lead to composition ingestion and contact with sensitive soft tissues in the oral cavity and digestive tract. Limiting this result of viscosity degradation is a significant and unexpected improvement over the water-soluble prior art compositions.
  • expiration dating of a particular composition (conducted typically at 25 degrees C. and 60% relative humidity to represent room temperature storage conditions and at 40 degrees C. and 75% relative humidity to represent accelerated or stressed storage conditions), limitations are placed on the expiration dating of a particular composition.
  • the expiration date represents that date beyond which the performance-related properties (such as remaining concentration of hydrogen peroxide and, in particular, viscosity) are observed or predicted to fall below a suitable established range.
  • manufacturers often have no choice but to recommend storage of tooth whitening compositions at refrigerated temperatures, which is inconvenient and time-consuming, but allows for the longer product shelf life demanded by dentists and dental distributors who cannot precisely predict when a product in inventory may be used or sold.
  • a number of thickened hydrogen peroxide gels are commercially available for whitening teeth. In order to preserve hydrogen peroxide potency over a reasonable shelf life (e.g., 12 to 18 months), it is necessary to store these commercial products in a refrigerated state, typically between 2 degrees C and 8 degrees C (36 degrees Fahrenheit to 46 degrees Fahrenheit).
  • Opalescence Boost Gel (Ultradent, South Jordan, UT) is a 45% hydrogen peroxide gel that despite its low pH of approximately 3.0 (which is more favorable for hydrogen peroxide stability than higher pH levels), the product must still be refrigerated to avoid loss of hydrogen peroxide potency and gel viscosity, both of which would lead to poor performance of the product as a tooth whitener.
  • Colgate Visible White Chairside gel (Colgate-Oral Pharmaceuticals, New York, NY), according to information on its MSDS, is a 40 - 50% hydrogen peroxide gel with a pH between 1.8 and 2.8, and thickened with silicon dioxide. Refrigerated storage is also recommended for this product to avoid premature degradation of gel potency and rheological properties. Both of these commercial products require refrigerated storage, which is often inconvenient in the limited space available in a typical dentist's office, and both products require a waiting period for the gels to equilibrate to room temperature before use, which is often not possible or is inconvenient due to tight patient scheduling windows.
  • the present invention is directed to highly storage- stable oxidizing compositions for general bleaching or whitening purposes, but in particular for whitening teeth, comprising (1) hydrogen peroxide and (2) a thickening polymer or copolymer comprising a pendant sulfonic acid group contributed by building block monomers such as 2-acrylamido-2-methylpropane sulfonic acid (AMPS). While not being bound to any particular theory, it is speculated that the pendant sulfonic acid moiety on the thickener polymer or copolymer contributes to the stability of the hydrogen peroxide. This is in stark contrast to prior art thickening polymers or copolymers which are not observed to possess such stabilizing abilities and in fact may contribute to more rapid degradation of the hydrogen peroxide in the composition.
  • AMPS 2-acrylamido-2-methylpropane sulfonic acid
  • the present invention is further directed to tooth whitening compositions comprising (1) hydrogen peroxide at a concentration between about 3 and 50% by weight, (2) a hydrogen peroxide stabilizer, and (3) a thickening polymer or copolymer comprising a pendant sulfonic acid group, said compositions being stable for extended periods of time when stored at room temperature.
  • the present invention is further directed to a method of using these compositions.
  • the highly stable oxidizing compositions of the present invention are comprised of an oxidizing compound and a thickening polymer containing a pendant sulfonic acid moiety.
  • the inventive compositions of the present invention are comprised of an oxidizing compound and a thickening polymer containing a pendant sulfonic acid moiety.
  • compositions may also contain optional components. Both the essential and optional components will be described more fully in the following paragraphs.
  • Oxidizing compounds contemplated to have utility in the formulation of the inventive compositions include hydrogen peroxide, carbamide peroxide, sodium percarbonate, calcium peroxide, PVP-hydrogen peroxide complexes, allyl methacrylate crosspolymer / hydrogen peroxide complexes, and other similar compounds that yield or generate hydrogen peroxide in the presence of water.
  • Thickening polymers containing a pendant sulfonic acid moiety that are contemplated to have utility in the formulation of the inventive compositions include 2- acrylamido-2-methylpropane sulfonic acid (AMPS) polymers and copolymers.
  • AMPS 2- acrylamido-2-methylpropane sulfonic acid
  • H 2 C CH— C N C CH 2 — S0 3 H
  • Polymers, copolymers and crosspolymers synthesized from AMPS include hydroxyethyl acrylate / sodium acryloyldimethyltaurate copolymer (Sepinov EMT-10 from Seppic S.A., a division of Air Liquide), ammonium acryloyldimethyl taurate / vinyl pyrrolidone copolymer (Aristoflex AVC, Clariant International LTD), ammonium acryloyldimethyltaurate / beheneth-25 methacrylate crosspolymer (Aristoflex HMB, Clariant International LTD), sodium acrylate / sodium acryloyldimethyltaurate copolymer (a component of Sepigel EG and Simulgel SMS 88, Seppic S.A.),
  • acrylamide / sodium acryloyldimethyltaurate copolymer (a component of Simulgel 600 and Simulgel 600 PHA, Seppic S.A.).
  • Optional components may be added or included in the inventive compositions in order to modify, preserve or enhance the performance or organoleptic characteristics.
  • Optional components include hydrogen peroxide stabilizers, humectants, secondary active ingredients, surface active agents, photoactive compounds, colorants, flavors, and sweeteners.
  • inventive compositions can be employed in a number of different methods of whitening teeth, including those intended for application to the teeth of a patient or subject by a dentist or other dental professional, and those intended for application by a patient or subject to his or her own teeth.
  • Tooth whitening methods involving application by a dentist or dental professional are referred to as “chairside” or “in-office” whitening procedures, and typically involve the placement of a tooth whitening gel directly onto the tooth surfaces or a subject while the subject is seated in a dental chair at a dental office, medspa, or other such setting.
  • Tooth whitening methods involving self-application of a tooth whitening composition by a subject are typically referred to as "take-home” or “over-the-counter” whitening procedures.
  • Take-home products may involve the fabrication of a custom-molded tray by a dentist or other dental professional, into which the tooth whitening gel is placed at home by the subject using a syringe, tube or other such container to dispense the gel.
  • Pre-molded or "one-size-fits-all" dental trays may be provided that are "pre-dosed” with a tooth whitening gel for subject or patient convenience.
  • Strips of material can be fashioned from various materials including deformable and non-deformable polymers and waxes, coated with a thin layer of tooth whitening gel and applied directly to the tooth surfaces in order to effect whitening.
  • Dispensing devices with integrated brushes, swabs or dauber applicators to allow for direct application of tooth whitening gels to the teeth surfaces may also be used effectively by a patient or subject. While not intended to impose any limitations to any particular method of use, it is contemplated that the present inventive compositions, due to their exceptional stability profiles, will be useful in all of the application modes and tooth whitening methods mentioned above, in particular when extended storage periods at room temperature are either desired or required.
  • composition above was manufactured by combining the water, glycerin, hydrogen peroxide, etidronic acid and potassium stannate in a Kynar-coated 2- gallon Ross mixing vessel and mixing with moderate to high shear agitation until the components were well blended. While continuing to mix, the hydroxyethyl acrylate / sodium acryloyldimethyltaurate copolymer was quickly added and the mixture agitated until the polymer powder was well dispersed and wetted out. The resulting mixture was then transferred to the Ross vacuum agitator, and slow agitation was begun under vacuum to defoam and deaerate the mixture.
  • the agitation was increased and continued under vacuum until the mixture became smooth, relatively clear and free from entrapped bubbles and/or air.
  • the mixture was then adjusted to a pH of about 5.0 with the ammonium hydroxide solution while continuing to mix under a vacuum.
  • the finished mixture a transparent to translucent gel, was then filled into plastic syringes for further testing.
  • Viscosity determination The viscosity of the gel of Example 1, as well as all of the other examples in the present invention, was determined by cone-plate viscometry using a Brookfield DVII+ Pro Viscometer (Brookfield Engineering) with cone-plate attachment. Cone-plate spindle 51Z was used and the conditions were 1 rpm spindle speed and temperature was held constant at 25 deg C using a circulating water bath. The viscosity 24 hours after manufacture was 39,353 centipoise.
  • pH Determination The pH of the gel of Example 1, as well as all of the other examples in the present invention, was determined using an Accumet AR15 pH/ISE meter (Fisher Scientific) and a standardized (two-point standardization at pH 4 and pH 7) combination pH probe. All samples were determined in neat form. The pH 24 hours after manufacture was 4.9.
  • Hydro en peroxide determination The hydrogen peroxide content, expressed as weight percent of the total composition weight, was determined using a standard iodometric titration (FMC Product Technical Guide: Hydrogen Peroxide Quantitative Test - Iodometric). The hydrogen peroxide concentration 24 hours after manufacture was 31.7% by weight of the entire composition.
  • Syringes of the gel from Example 1 were placed in a controlled environment storage chamber at 40 degrees C. and 75% relative humidity. For the first 12 weeks, samples were drawn from the stored syringes and allowed to equilibrate to room temperature overnight. Thereafter, test samples were drawn on a monthly basis.
  • Viscosity, pH and hydrogen peroxide determination tests were performed as described above and the values are reported in Table 1 below.
  • the gel of Example 1 possesses a high degree of stability with respect to viscosity, pH and hydrogen peroxide content. Regression analysis of the above data indicates that all of the physical properties tested will remain within +/-10% range of the initially reported numbers for pH and hydrogen peroxide concentration and within +/20 of the initially reported numbers for viscosity for at least 24 weeks, which is a high standard of control for performance specifications. Accelerated product aging is typically used to justify expiration dating for new products when room temperature stability testing would delay the introduction of a product to market. Typically, a product stored at 40 degrees C.
  • a cheek retractor was placed in the subject's mouth and soft tissues adjacent to the buccal tooth enamel were isolated using a light-cured resin dam
  • Example 1 gel was dispensed from a syringe directly onto and brushed evenly over the buccal tooth surfaces to be whitened, three of which (teeth #6 -
  • Example 2 The composition of Example 2 was manufactured in the same manner as in Example 1, resulting in a translucent gel that was packaged into polypropylene syringes.
  • the Example 2 gel syringes were subjected to a high temperature stress test to determine the gel's ability to maintain functional properties under extremes of
  • the comparative stability of the hydrogen peroxide gel of Example 2 was compared to that of a commercially available hydrogen peroxide gel used for tooth whitening in a chairside setting (Opalescence Boost, Ultradent Products, South Jordan, UT).
  • the hydrogen peroxide concentration of the Boost gel was determined to be 46% using the method previously described, and which is similar to the concentration of hydrogen peroxide in the gel of Example 2 (45%).
  • Three samples of both gels (in syringes) were placed in a constant temperature oven set to 85 degrees C for a period of 6 hours, during which the syringes were observed for any movement of the plunger (an indication of poor hydrogen peroxide stability).
  • composition is designed to be utilized in a patient- or subject- applied tooth whitening method involving a dental tray fabricated by a dentist or dental professional.
  • Table 2 contains a summary of the approximate ranges of concentrations (on a weight percent basis) for various components that may be present in the inventive compositions.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Emergency Medicine (AREA)
  • Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Cosmetics (AREA)
  • Thermotherapy And Cooling Therapy Devices (AREA)

Abstract

L'invention concerne des compositions épaissies à haute stabilité pour blanchir les dents qui contiennent des hauts niveaux de peroxyde d'hydrogène mais qui ne nécessitent pas d'être soumises à une réfrigération ou à d'autres conditions de stockage spéciales pour présenter une durée de vie prolongée.
PCT/US2010/054873 2009-10-30 2010-10-29 Compositions oxydantes à haute stabilité WO2011053877A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US25682109P 2009-10-30 2009-10-30
US61/256,821 2009-10-30

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WO2011053877A2 true WO2011053877A2 (fr) 2011-05-05
WO2011053877A3 WO2011053877A3 (fr) 2012-11-22

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Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ITMI20110873A1 (it) * 2011-05-18 2012-11-19 Tommaso Zuccheri Composizione sbiancante in forma di gel e relativo uso per lo sbiancamento dentale
US20160106641A1 (en) * 2014-10-20 2016-04-21 Oraceutical Llc Stable compositions for whitening teeth and methods of using same
WO2017019321A1 (fr) * 2015-07-28 2017-02-02 The Procter & Gamble Company Compositions d'hygiène buccale contenant des polymères, des copolymères ou des polymères réticulés amps
WO2017024110A1 (fr) 2015-08-04 2017-02-09 Isp Investments Llc Polymères dérivés d'éthers d'alcool vinylique à fonction amino et leurs applications
US20170281486A1 (en) * 2016-04-01 2017-10-05 The Procter & Gamble Company Oral Care Compositions Containing Potassium Nitrate and Peroxide
WO2017173197A1 (fr) * 2016-04-01 2017-10-05 The Procter & Gamble Company Compositions de soin bucco-dentaire contenant une phase de réseaux de gel et du nitrate de potassium
US20170281476A1 (en) * 2016-04-01 2017-10-05 The Procter & Gamble Company Oral Care Compositions Containing A Gel Network Phase
US20170281493A1 (en) * 2016-04-01 2017-10-05 The Procter & Gamble Company Oral Care Compositions With An Effective Flavor Display
US10219988B2 (en) 2016-04-01 2019-03-05 The Procter & Gamble Company Oral care compositions containing gel networks and potassium nitrate
EP3628375A1 (fr) * 2018-09-27 2020-04-01 Unilever N.V. Composition d'hygiène buccale
EP3288532B1 (fr) 2015-04-28 2021-06-23 Basf Se Polymères pour la stabilisation des composes peroxydiques

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EP1314419B1 (fr) * 1995-09-25 2009-08-05 Discus Dental, LLC Compositions pour blanchir les dents
HUP0401326A2 (en) * 2001-08-17 2004-10-28 Smithkline Beecham Plc Novel device
US7022144B2 (en) * 2002-12-09 2006-04-04 L'oreal Oxidizing compositions containing a mixture of polymers including at least one copolymer based on acrylamide and 2-acrylamido-2-methylpropanesulphonic acid
US7217298B2 (en) * 2003-01-16 2007-05-15 L'oreal S.A. Ready-to-use bleaching compositions, preparation process and bleaching process
US7264471B2 (en) * 2004-05-05 2007-09-04 Ultradent Products, Inc. Methods and kits for bleaching teeth while protecting adjacent gingival tissue
US20060198797A1 (en) * 2005-11-07 2006-09-07 Giniger Martin S Stand-alone or enhancer composition for oral care
FR2907001B1 (fr) * 2006-10-12 2012-12-14 Seppic Sa Agent de decoloration ; procede pour sa preparation et utilisation pour decolorer les cheveux et blanchir les dents

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Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ITMI20110873A1 (it) * 2011-05-18 2012-11-19 Tommaso Zuccheri Composizione sbiancante in forma di gel e relativo uso per lo sbiancamento dentale
US20160106641A1 (en) * 2014-10-20 2016-04-21 Oraceutical Llc Stable compositions for whitening teeth and methods of using same
EP3288532B1 (fr) 2015-04-28 2021-06-23 Basf Se Polymères pour la stabilisation des composes peroxydiques
CN107847402A (zh) * 2015-07-28 2018-03-27 宝洁公司 含有amps聚合物、共聚物或交联聚合物的口腔护理组合物
WO2017019321A1 (fr) * 2015-07-28 2017-02-02 The Procter & Gamble Company Compositions d'hygiène buccale contenant des polymères, des copolymères ou des polymères réticulés amps
WO2017024110A1 (fr) 2015-08-04 2017-02-09 Isp Investments Llc Polymères dérivés d'éthers d'alcool vinylique à fonction amino et leurs applications
CN109069362A (zh) * 2016-04-01 2018-12-21 宝洁公司 含有硝酸钾和过氧化物的口腔护理组合物
AU2017240033B2 (en) * 2016-04-01 2020-01-30 The Procter & Gamble Company Oral care compositions containing a gel network phase and potassium nitrate
US20170281493A1 (en) * 2016-04-01 2017-10-05 The Procter & Gamble Company Oral Care Compositions With An Effective Flavor Display
WO2017173272A1 (fr) * 2016-04-01 2017-10-05 The Procter & Gamble Company Compositions de soin buccal contenant du nitrate de potassium et du peroxyde
WO2017173197A1 (fr) * 2016-04-01 2017-10-05 The Procter & Gamble Company Compositions de soin bucco-dentaire contenant une phase de réseaux de gel et du nitrate de potassium
US10219988B2 (en) 2016-04-01 2019-03-05 The Procter & Gamble Company Oral care compositions containing gel networks and potassium nitrate
AU2017240683B2 (en) * 2016-04-01 2020-01-16 The Procter & Gamble Company Oral care compositions containing potassium nitrate and peroxide
US20170281476A1 (en) * 2016-04-01 2017-10-05 The Procter & Gamble Company Oral Care Compositions Containing A Gel Network Phase
AU2017240034B2 (en) * 2016-04-01 2020-02-06 The Procter & Gamble Company Oral care compositions containing a gel network phase
US11517509B2 (en) 2016-04-01 2022-12-06 The Procter & Gamble Company Oral care compositions containing a gel network phase
US10758461B2 (en) 2016-04-01 2020-09-01 The Procter & Gamble Company Oral care compositions containing a gel network phase and potassium nitrate
US10765610B2 (en) 2016-04-01 2020-09-08 The Procter & Gamble Company Oral care compositions containing potassium nitrate and peroxide
US10925820B2 (en) 2016-04-01 2021-02-23 The Procter & Gamble Company Oral care compositions with an effective flavor display
US20170281486A1 (en) * 2016-04-01 2017-10-05 The Procter & Gamble Company Oral Care Compositions Containing Potassium Nitrate and Peroxide
EP3628375A1 (fr) * 2018-09-27 2020-04-01 Unilever N.V. Composition d'hygiène buccale

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