WO1997003641A1 - Dental care product containing polyolefine wax - Google Patents

Dental care product containing polyolefine wax

Info

Publication number
WO1997003641A1
WO1997003641A1 PCT/EP1996/002930 EP9602930W WO9703641A1 WO 1997003641 A1 WO1997003641 A1 WO 1997003641A1 EP 9602930 W EP9602930 W EP 9602930W WO 9703641 A1 WO9703641 A1 WO 9703641A1
Authority
WO
WIPO (PCT)
Prior art keywords
wax
dental care
care product
product containing
particle size
Prior art date
Application number
PCT/EP1996/002930
Other languages
German (de)
French (fr)
Inventor
Michael Wolfgang MÜLLER
Horst Westenfelder
Franz Frosch
Original Assignee
Basf Aktiengesellschaft
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 Basf Aktiengesellschaft filed Critical Basf Aktiengesellschaft
Publication of WO1997003641A1 publication Critical patent/WO1997003641A1/en

Links

Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73Polysaccharides
    • A61K8/731Cellulose; Quaternized cellulose derivatives
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8105Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • A61K8/8111Homopolymers or copolymers of aliphatic olefines, e.g. polyethylene, polyisobutene; Compositions of derivatives of such polymers

Definitions

  • the present invention relates to pasty dentifrices containing 1 to 30% by weight of polyolefin wax with an average particle size of 5 to 45 ⁇ m.
  • the invention further relates to the use of polyolefin wax with an average particle size of 5 to 45 ⁇ m as an abrasive in pasty dentifrices.
  • Dental care products generally contain abrasives that support the mechanical cleaning effect of the toothbrush.
  • No. 3,955,942 describes abrasives which are contained in toothpaste and which consist of agglomerates of small inorganic particles.
  • DE-A 21 04 473 describes waxes as a matrix substance for active substances contained in toothpaste.
  • abrasives based on inorganic material lead to damage to the tooth enamel due to their coarse grinding action or, particularly in the case of older people with partially exposed dentin, to the tooth necks.
  • the object of the present invention was therefore to provide pasty dental care products with a mild but effective abrasive.
  • Suitable polyolefin waxes of the dental care agent according to the invention are polymers of ethylene, including, in addition to linear polyethylene of high, medium and low density (HDPE, MDPE, LLDPE), especially high-pressure polyethylene of low density (LDPE); furthermore syndiotactic and preferably isotactic polypropylene wax, and copolymers of 0.1 to 99.9 mol%
  • Suitable waxes of the dentifrice according to the invention have an average particle size in the range from 5 to 45 ⁇ m and preferably in the range from 8 to 15 ⁇ m.
  • melt viscosity in the range from 100 to 1000 mm 2 / s, preferably in the range from 110 to 500 mm 2 / s, measured according to DGF M-III 8 at 120 ° C.
  • Polyethylene waxes from the high-pressure and low-pressure processes ie waxes from ethylene homo- or C 3 - to Cs copolymers whose density is in the range from 0.910 to 0.970 g / cm 3, are particularly suitable.
  • the polyolefin waxes according to the definition are generally known, in some cases commercially available and otherwise obtainable in a known manner, for example by Ziegler, metallocene (EP-A 602 509, EP-A 571 882), Phillips or high-pressure polymerization of ethylene or alkylene 1-enes, or by degrading the high molecular weight olefin polymers on which the waxes are based (Ullmanns Encyklopadie der Technische Chemie, 4th edition, vol. 24, pp. 1-49, in particular pp. 36 to 45, (1983)).
  • the waxes are generally micronized using standard methods.
  • polyolefin waxes whose density, measured according to DGF M-III 2a (57), is in the range from 0.900 to 0.990 g / cm 3 , preferably in the range from 0.910 to 0.970 g / cm 3 .
  • the dentifrice according to the invention contains the ingredients and types customary for dentifrices in terms of type and quantity (GA NOWAK, The Cosmetic Preparations, Volume 2, 3rd Edition 1984, Chapter 15) such as, for example, cleaning and polishing materials, for example calcium carbonate , surface-active substances, active substances, mucilages, thixotropic agents, taste and aroma substances, humectants, preservatives and coloring substances.
  • cleaning and polishing materials for example calcium carbonate , surface-active substances, active substances, mucilages, thixotropic agents, taste and aroma substances, humectants, preservatives and coloring substances.
  • the polyolefin waxes are contained in the dentifrice according to the invention in an amount of 1 to 30% by weight, preferably 5 to 15% by weight, based on the dentifrice.
  • the conventional inorganic abrasives such as precipitated calcium carbonate, silica, calcium phosphate or aluminum oxide, may also be present in minor amounts in the dentifrices according to the invention.
  • the content of the wax in the mixture of polyolefin wax and solid inorganic constituents of the dentifrice is then generally in the range from 3 to 60% by weight.
  • the dentifrice according to the invention can be in the form of toothpaste, toothpaste or tooth gel.
  • the dentifrice according to the invention can be briefly swollen, for example, by mixing the components, for example in a mixer of the Bäko-Mix brand, and subsequent homogenization can be obtained under vacuum.
  • the RDA is determined using a method from Missouri Analytical Laboratories, Inc.
  • RDA is rasion for radioactive dentin waste first In this test, extracted human teeth are irradiated radioactive and then cleaned with the test toothpaste and a reference material. The radioactivity is measured in the abrasion.
  • the RDA value for the reference material is set to 100 and the test measured values based on it.
  • Example 1 The experiment of Example 1 was repeated, but the polyethylene wax Luvitol® PE 10 was completely replaced by silica gel.
  • the toothpaste was found to have a rough, highly abrasive effect and the tooth necks were attacked, the RDA value was high.

Abstract

Dental care product in paste form containing 1 to 30 wt.% polyolefine wax with an average particle size of 5 to 45 νm.

Description

Polyolefinwachs enthaltende ZahnpflegemittelDentifrices containing polyolefin wax
Beschreibungdescription
Die vorliegende Erfindung betrifft pastöse Zahnpflegemittel, ent¬ haltend 1 bis 30 Gew.-% Polyolefinwachs der mittleren Teilchen¬ größe 5 bis 45 μm.The present invention relates to pasty dentifrices containing 1 to 30% by weight of polyolefin wax with an average particle size of 5 to 45 μm.
Weiterhin betrifft die Erfindung die Verwendung von Polyolefin- wachs der mittleren Teilchengröße 5 bis 45 μm als Schleifmittel in pastösen Zahnpflegemitteln.The invention further relates to the use of polyolefin wax with an average particle size of 5 to 45 μm as an abrasive in pasty dentifrices.
Zahnpflegemittel enthalten im allgemeinen Schleifmittel welche die mechanisch-reinigende Wirkung der Zahnbürste unterstützen.Dental care products generally contain abrasives that support the mechanical cleaning effect of the toothbrush.
Die US 3,955,942 beschreibt Schleifmittel die in Zahnpasta ent¬ halten sind und die aus Agglomeraten von kleinen anorganischen Pa-rtikeln bestehen.No. 3,955,942 describes abrasives which are contained in toothpaste and which consist of agglomerates of small inorganic particles.
Die DE-A 21 04 473 beschreibt Wachse als Matrixsubstanz für Wirk¬ stoffe, die in Zahnpasta enthalten sind.DE-A 21 04 473 describes waxes as a matrix substance for active substances contained in toothpaste.
Schleifmittel auf der Basis von anorganischem Material führen je- doch wegen ihrer groben SchleifWirkung zu Schädigungen des Zahn¬ schmelzes oder, besonders bei älteren Personen mit teilweise freiliegendem Zahnbein, zur Schädigung der Zahnhälse.However, abrasives based on inorganic material lead to damage to the tooth enamel due to their coarse grinding action or, particularly in the case of older people with partially exposed dentin, to the tooth necks.
Aufgabe der vorliegenden Erfindung war es daher, pastöse Zahn- Pflegemittel mit einem milden, aber wirksamen Schleifmittel zur Verfügung zu stellen.The object of the present invention was therefore to provide pasty dental care products with a mild but effective abrasive.
Demgemäß wurden pastöse Zahnpflegemittel, enthaltend 1 bis 30 Gew.-% Polyolefinwachs der mittleren Teilchengröße 5 bis 45 μm gefunden.Accordingly, pasty dentifrices containing 1 to 30% by weight of polyolefin wax with an average particle size of 5 to 45 μm have been found.
Außerdem wurde die Verwendung von Polyolefinwachs als Schleif¬ mittel in Zahnpflegemitteln gefunden.The use of polyolefin wax as an abrasive in dentifrices has also been found.
Als geeignete Polyolefinwachse des erfindungsgemäßen Zahnpflege¬ mittels verwendet man Polymerisate des Ethylens, darunter neben linearem Polyethylen hoher, mittlerer und niedriger Dichte (HDPE, MDPE, LLDPE) vor allem Hochdruck-Polyethylen niedriger Dichte (LDPE) ; ferner syndiotaktisches und vorzugsweise isotaktisches Polypropylenwachs, sowie Copolymerisate aus 0,1 bis 99,9 Mol-%Suitable polyolefin waxes of the dental care agent according to the invention are polymers of ethylene, including, in addition to linear polyethylene of high, medium and low density (HDPE, MDPE, LLDPE), especially high-pressure polyethylene of low density (LDPE); furthermore syndiotactic and preferably isotactic polypropylene wax, and copolymers of 0.1 to 99.9 mol%
Ethylen und 99,9 bis 0,1 Mol-% eines C3- bis Cs-Alk-l-ens, wie vor allem Propylen; weitere geeignete Alk-1-ene sind z.B. But-l-en, Pent-1-en, Hex-l-en, Oct-l-en und 4-Methylpent-l-en sowie Ge¬ mische von Alk-1-enen.Ethylene and 99.9 to 0.1 mol% of a C 3 - to Cs-alk-1-ene, such as especially propylene; further suitable alk-1-enes are, for example, but-l-enes, Pent-1-ene, hex-1-ene, oct-1-ene and 4-methylpent-l-ene and mixtures of alk-1-enes.
Geeignete Wachse des erfindungsgemäßen Zahnpflegemittels haben eine mittlere Teilchengröße im Bereich von 5 bis 45 μm und vor¬ zugsweise im Bereich von 8 bis 15 μm.Suitable waxes of the dentifrice according to the invention have an average particle size in the range from 5 to 45 μm and preferably in the range from 8 to 15 μm.
Sie haben im allgemeinen eine Schmelzeviskosität im Bereich von 100 bis 1000 mm2/s, vorzugsweise im Bereich von 110 bis 500 mm2/s, gemessen nach DGF M-III 8 bei 120°C.They generally have a melt viscosity in the range from 100 to 1000 mm 2 / s, preferably in the range from 110 to 500 mm 2 / s, measured according to DGF M-III 8 at 120 ° C.
Besonders gut geeignet sind Polyethylenwachse aus den Hochdruck- und Niederdruckprozessen, also Wachse aus Ethylen-Homo- oder C3- bis Cs-Copolymerisaten deren Dichte im Bereich von 0,910 bis 0,970 g/cm3 liegt.Polyethylene waxes from the high-pressure and low-pressure processes, ie waxes from ethylene homo- or C 3 - to Cs copolymers whose density is in the range from 0.910 to 0.970 g / cm 3, are particularly suitable.
Die definitionsgemäßen Polyolefinwachse sind allgemein bekannt, zum Teil handelsüblich und im übrigen in bekannter Weise erhält¬ lich, beispielsweise durch Ziegler-, Metallocen- (EP-A 602 509, EP-A 571 882) , Phillips- oder Hochdruckpolymerisation von Ethylen oder Alk-1-enen, oder indem man den Wachsen zugrunde liegende hochmolekulare Olefinpolymerisate abbaut (Ullmanns Encyklopädie der technischen Chemie, 4. Auflage, Bd. 24, S. 1-49, insbesondere S. 36 bis S. 45, (1983) ) .The polyolefin waxes according to the definition are generally known, in some cases commercially available and otherwise obtainable in a known manner, for example by Ziegler, metallocene (EP-A 602 509, EP-A 571 882), Phillips or high-pressure polymerization of ethylene or alkylene 1-enes, or by degrading the high molecular weight olefin polymers on which the waxes are based (Ullmanns Encyklopadie der Technische Chemie, 4th edition, vol. 24, pp. 1-49, in particular pp. 36 to 45, (1983)).
Die Wachse werden im allgemeinen mit den üblichen Verfahren mikronisiert.The waxes are generally micronized using standard methods.
Besonders gut geeignet sind Polyolefinwachse deren Dichte, gemes sen nach DGF M-III 2a (57), im Bereich von 0,900 bis 0,990 g/cm3, vorzugsweise im Bereich von 0,910 bis 0,970 g/cm3 liegt.Particularly suitable are polyolefin waxes whose density, measured according to DGF M-III 2a (57), is in the range from 0.900 to 0.990 g / cm 3 , preferably in the range from 0.910 to 0.970 g / cm 3 .
Neben den Polyolefinwachsen enthält das erfindungsgemäße Zahn- pflegemittel die für Zahnpflegemittel in Art und Menge üblichen Bestandteile, (G.A. NOWAK, Die kosmetischen Präparate, Band 2, 3. Auflage 1984, Kapitel 15) wie beispielsweise Putz- und Polier¬ stoffe, zum Beispiel Calciumcarbonat, oberflächenaktive Stoffe, Wirkstoffe, Schleimstoffe, Thixotropiermittel, Geschmacks- und Aromastoffe, Feuchthaltemittel, Konservierungsstoffe und Farb- Stoffe.In addition to the polyolefin waxes, the dentifrice according to the invention contains the ingredients and types customary for dentifrices in terms of type and quantity (GA NOWAK, The Cosmetic Preparations, Volume 2, 3rd Edition 1984, Chapter 15) such as, for example, cleaning and polishing materials, for example calcium carbonate , surface-active substances, active substances, mucilages, thixotropic agents, taste and aroma substances, humectants, preservatives and coloring substances.
Die Polyolefinwachse sind in dem erfindungsgemäßen Zahnpflege¬ mittel zu 1 bis 30 Gew.-%, vorzugsweise zu 5 bis 15 Gew.-%, bezo¬ gen auf das Zahnpflegemittel enthalten. Daneben können, in untergeordneter Menge, in den erfindungs- gemäßen Zahnpflegemitteln auch die üblichen anorganischen Schleifmittel, wie beispielsweise gefälltes Calciumcarbonat, Kie¬ selsäure, Calciumphosphat oder Aluminiumoxid enthalten sein.The polyolefin waxes are contained in the dentifrice according to the invention in an amount of 1 to 30% by weight, preferably 5 to 15% by weight, based on the dentifrice. In addition, the conventional inorganic abrasives, such as precipitated calcium carbonate, silica, calcium phosphate or aluminum oxide, may also be present in minor amounts in the dentifrices according to the invention.
Der Gehalt des Wachses in der Mischung aus Polyolefinwachs und festen anorganischen Bestandteilen des Zahnpflegemittels liegt dann im allgemeinen im Bereich von 3 bis 60 Gew.-%.The content of the wax in the mixture of polyolefin wax and solid inorganic constituents of the dentifrice is then generally in the range from 3 to 60% by weight.
Das erfindungsgemäße Zahnpflegemittel kann als Zahnpasta, Zahn¬ creme oder als Zahngel vorliegen.The dentifrice according to the invention can be in the form of toothpaste, toothpaste or tooth gel.
Das erfindungsgemäße Zahnpflegemittel kann beispielsweise durch Mischen der Komponenten, beispielsweise in einem Mixer der Marke Bäko-Mix, kurzes quellen lassen und anschließende Homogenisierung unter Vakuum erhalten werden.The dentifrice according to the invention can be briefly swollen, for example, by mixing the components, for example in a mixer of the Bäko-Mix brand, and subsequent homogenization can be obtained under vacuum.
Es eignet sich besonders gut zur Zahnpflege empfindlicher Zähne.It is particularly suitable for dental care of sensitive teeth.
Beispiele 1 und 2Examples 1 and 2
Es wurden unterschiedliche Zahncremes abgemischt. Mit diesen Zahncremes putzten sich dann 10 Probanden die Zähne und beurteil¬ ten die Wirkung der Zahncreme qualitativ. Außerdem wurden die Zahnhälse auf Verletzungen untersucht. Desweiteren wurde der RDA- Wert bestimmt (Tabelle) .Different toothpastes were mixed. With these toothpastes, 10 test subjects then brushed their teeth and qualitatively assessed the effect of the toothpaste. The tooth necks were also examined for injuries. Furthermore, the RDA value was determined (table).
Der RDA-Wert wird nach einer Methode der Missouri Analytical Laboratories, Inc. bestimmt. RDA steht für radioaktive Dentin-Ab-1 rasion. In diesem Test werden extrahierte menschliche Zähne ra¬ dioaktiv bestrahlt und dann mit der Testzahncreme und einem Referenzmaterial geputzt. Im Abrieb wird die Radioaktivität ge¬ messen. Der RDA-Wert für das Referenzmaterial wird auf 100 ge¬ setzt und die Testmeßwerte darauf bezogen.The RDA is determined using a method from Missouri Analytical Laboratories, Inc. RDA is rasion for radioactive dentin waste first In this test, extracted human teeth are irradiated radioactive and then cleaned with the test toothpaste and a reference material. The radioactivity is measured in the abrasion. The RDA value for the reference material is set to 100 and the test measured values based on it.
In allen erfindungsgemäßen Fällen wurde eine angenehme und gute SchleifWirkung der Zahnpasta festgestellt, wobei die Zahnhälse von Verletzungen verschont blieben.In all cases according to the invention a pleasant and good grinding effect of the toothpaste was found, the tooth necks being spared from injuries.
Vergleichsbeispiel VIComparative Example VI
Der Versuch von Beispiel 1 wurde wiederholt, jedoch wurde das Polyethylenwachs Luvitol ® PE 10 vollständig gegen Kieselgel aus¬ getauscht. Hier wurde eine rauhe, stark scheuernde Wirkung der Zahncreme festgestellt und die Zahnhälse wurden angegriffen, der RDA-Wert war hoch.The experiment of Example 1 was repeated, but the polyethylene wax Luvitol® PE 10 was completely replaced by silica gel. Here the toothpaste was found to have a rough, highly abrasive effect and the tooth necks were attacked, the RDA value was high.
Tabelletable
Zahncremes mit Luvitol PE 10 und/oder KieselgelToothpastes with Luvitol PE 10 and / or silica gel
Figure imgf000006_0001
a) Sorbit der Firma E. Merck
Figure imgf000006_0001
a) Sorbitol from E. Merck
b) Kieselgel der Firma Graceb) Grace's silica gel
c) Mikronisiertes Polyethylenwachs der Firma BASF Dichte (DGF M-III 2a) 0,940-0,955 g/cm3, Teilchengröße <10 μm.c) Micronized polyethylene wax from BASF Density (DGF M-III 2a) 0.940-0.955 g / cm 3 , particle size <10 μm.
d) Carboxymethylcellulose der Firma Hoechstd) carboxymethyl cellulose from Hoechst
Natriummonofluorphosphat der Firma GiulliniSodium monofluorophosphate from Giullini
Kieselgel der Firma Degussa Silica gel from Degussa

Claims

Patentansprüche claims
1. Pastöse Zahnpflegemittel, enthaltend 1 bis 30 Gew.-% Polyole- finwachs der mittleren Teilchengröße 5 bis 45 μm.1. Pasty dentifrice containing 1 to 30% by weight of polyolefin wax with an average particle size of 5 to 45 μm.
2. Pastöse Zahnpflegemittel, nach Anspruch 1 wobei das Polyole- finwachs ein Polyethylenwachs ist.2. Pasty dentifrice according to claim 1, wherein the polyolefin wax is a polyethylene wax.
3. Pastöse Zahnpflegemittel, nach Anspruch 1, wobei das Polyole- finwachs eine Dichte im Bereich von 0,900 bis 0,990 g/cm3 hat.3. Pasty dentifrice according to claim 1, wherein the polyolefin wax has a density in the range from 0.900 to 0.990 g / cm 3 .
4. Verwendung von Polyolefinwachs der mittleren Teilchengröße 5 bis 45 μm als Schleifmittel in pastösen Zahnpflegemitteln.4. Use of polyolefin wax with an average particle size of 5 to 45 μm as an abrasive in pasty dentifrices.
5. Verwendung von Polyolefinwachs der mittleren Teilchengröße 5 bis 45 μm und einer Dichte von 0,900 bis 0,990 g/cm3 als Schleifmittel in pastösen Zahnpflegemitteln. 5. Use of polyolefin wax with an average particle size of 5 to 45 μm and a density of 0.900 to 0.990 g / cm 3 as an abrasive in pasty dentifrices.
PCT/EP1996/002930 1995-07-18 1996-07-04 Dental care product containing polyolefine wax WO1997003641A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19526078.3 1995-07-18
DE19526078 1995-07-18

Publications (1)

Publication Number Publication Date
WO1997003641A1 true WO1997003641A1 (en) 1997-02-06

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Country Status (1)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009149030A2 (en) * 2008-06-04 2009-12-10 The Procter & Gamble Company Oral care compositions and methods
US8735465B2 (en) 2010-03-10 2014-05-27 The Procter & Gamble Company Denture adhesive compositions

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
LU52524A1 (en) * 1965-12-07 1967-06-07
DE1492209A1 (en) * 1963-06-21 1970-01-02 Unilever Nv Polishes
US4007259A (en) * 1973-11-02 1977-02-08 Colgate-Palmolive Company Dental cream
JPS5736245A (en) * 1980-08-14 1982-02-27 Matsushita Electric Works Ltd YANESEKOHO
DE4330342A1 (en) * 1993-09-08 1995-03-09 Basf Ag Stable aqueous polyolefin wax dispersions

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1492209A1 (en) * 1963-06-21 1970-01-02 Unilever Nv Polishes
LU52524A1 (en) * 1965-12-07 1967-06-07
US4007259A (en) * 1973-11-02 1977-02-08 Colgate-Palmolive Company Dental cream
JPS5736245A (en) * 1980-08-14 1982-02-27 Matsushita Electric Works Ltd YANESEKOHO
DE4330342A1 (en) * 1993-09-08 1995-03-09 Basf Ag Stable aqueous polyolefin wax dispersions

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Week 8234, Derwent World Patents Index; AN 72-67933t, XP002018725 *

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009149030A2 (en) * 2008-06-04 2009-12-10 The Procter & Gamble Company Oral care compositions and methods
WO2009149030A3 (en) * 2008-06-04 2011-04-14 The Procter & Gamble Company Oral care compositions and methods
AU2009256366B2 (en) * 2008-06-04 2014-09-04 The Procter & Gamble Company Oral care compositions and methods
US8735465B2 (en) 2010-03-10 2014-05-27 The Procter & Gamble Company Denture adhesive compositions
US9463145B2 (en) 2010-03-10 2016-10-11 The Procter & Gamble Company Denture adhesive compositions

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