CA2140370A1 - Liquid tooth-cleaning formulations - Google Patents

Liquid tooth-cleaning formulations

Info

Publication number
CA2140370A1
CA2140370A1 CA002140370A CA2140370A CA2140370A1 CA 2140370 A1 CA2140370 A1 CA 2140370A1 CA 002140370 A CA002140370 A CA 002140370A CA 2140370 A CA2140370 A CA 2140370A CA 2140370 A1 CA2140370 A1 CA 2140370A1
Authority
CA
Canada
Prior art keywords
tooth
hydroxypropyl
weight
cleaning formulations
present
Prior art date
Legal status (The legal status 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 status listed.)
Abandoned
Application number
CA002140370A
Other languages
French (fr)
Inventor
Klaus Schumann
Franz Foerg
Claus Gutzschebauch
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Henkel AG and Co KGaA
Original Assignee
Individual
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 Individual filed Critical Individual
Publication of CA2140370A1 publication Critical patent/CA2140370A1/en
Abandoned legal-status Critical Current

Links

Classifications

    • 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
    • A61K8/737Galactomannans, e.g. guar; Derivatives thereof
    • 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
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41Amines
    • A61K8/416Quaternary ammonium compounds
    • 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
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • 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
    • 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
    • A61K8/733Alginic acid; Salts thereof
    • 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
    • A61K8/90Block copolymers
    • 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
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/59Mixtures
    • A61K2800/594Mixtures of polymers

Abstract

The invention concerns liquid tooth-cleaning agents which keep their flow properties over a long period. These properties are ensured by the use of xanthane as a consistency regulator in conjunction with (a) a hydroxypropyl-substituted hydrocolloid or (b) a cationic nitrogen-containing surfactant or (c) an ampholytic surfactant or (d) an N-acyl-sarcisinate or (e) an N-acyl-tauride or (f) a poly(ethylene glycol)/poly(propylene glycol) copolymer with an average molecular weight of 1,000 to 5,000 or a combina-tion of the compounds listed in (a) to (f).

Description

21~0370 WO 9~01080 PCT/EP93/01701 Liquid tooth-cleaning formulations This invention relates to liquid tooth-cleaning formulations which show long-term fluidity.
Toothpastes normally exhibit pseudoplastic behavior and can be characterized by their yield point. They may be extruded from a tube and assume a stable position on the toothbrush. However, this formulation requires some care on the part of the user during extrusion because the toothpaste can emerge suddenly from the tube. In such an event, part of the strand of toothpaste often drops off on application to the toothbrush or on insertion of the toothbrush into the mouth and remains unused in the oral cavity or in the wash basin.
The problem addressed by the present invention was to provide a liquid tooth-cleaning formulation showing long-term fluidity. In the context of the invention, long-term fluidity means that the tooth-cleaning formula-tion is present in liquid form and, depending on the viscosity to which it is adjusted, issues thinly from a storage container or can be removed dropwise from a container and that the consistency established is retain-ed for a prolonged period until the formulation has been used up. The tooth-cleaning formulation according to the invention would penetrate between the bristle heads immediately on application to the toothbrush and not after a few brushing movements, as is the case with conventional toothpastes. After application, the liquid tooth-cleaning formulation would remain on and between the bristles pending use and would not run down the bristle shafts. A liquid tooth-cleaning formulation such as this would lend itself to exact dispensing and hence to very economic use. There would be no need for direct contact between the storage container and the brush in 214037~
-
2 PCT/EP93/01701 contrast to toothpastes extruded from a tube. This would provide for particularly hygienic application. In addition, a liquid tooth-cleaning formulation would enable the storage container to be completely emptied 5 which is not possible with tubes of toothpaste.
The fact that the tooth-cleaning formulation would be present in liquid form would not of course affect the actual tooth-cleaning and dental-care properties of the formulation.
It is known from DE-A5 16 67 871 that the hydrocol-loid, xanthan, can be used as a suspending and thickening agent in liquid dental-care formulations.
However, it has been found that the need for long-term fluidity is not satisfied when xanthan is used in 15 the presence of silica abrasives. Thus, the fluidity of a liquid dental-care formulation of the type in question diminishes after a short time through the development of excessive yield points and dynamic viscosities.
It has now surprisingly been found that a liquid 20 tooth-cleaning formulation retains its fluidity in the long term providing xanthan is used in conjunction with certain viscosity stabilizers as a consistency regulator.
In the context of the invention, the viscosity stabili-zers in question are substances which prevent gradual 25 "after-thickening" of the liquid tooth-cleaning formula-tion, i.e. the development of a high yield point.
The viscosity stabilizers according to the invention are:

30 a) hydroxypropyl-substituted hydrocolloids or b) cationic nitrogen-containing surfactants or c) ampholytic surfactants or d) N-acyl sarcosinates or e) N-acyl taurides or 35 f) polyethylene glycol/polypropylene glycol copolymers 2lln37~
3 PCT/EP93/01701 with an average molecular weight of 1,000 to 5,000.

Accordingly, the present invention relates to water-and humectant-containing tooth-cleaning formulations in the form of a liquid preparation with long-term fluidity and a viscosity of 2,000 to 10,000 and preferably 5,000 to 8,000 mPa-s at 25C, xanthan in a quantity of 0.02 to 3.0% by weight being present as consistency regulator and a compound selected from the group consisting of a) hydroxypropyl-substituted hydrocolloids or b) cationic nitrogen-containing surfactants or c) ampholytic surfactants or d) N-acyl sarcosinates or e) N-acyl taurides or f) polyethylene glycol/polypropylene glycol copolymers with an average molecular weight of 1,000 to 5,000 in a quantity of 0.01 to 5.0% by weight or a combination of the compounds mentioned under a) to f) in a quantity of 0.01 to 10% by weight being present as viscosity stabilizer (all the percentages by weight mentioned being based on the tooth-cleaning formulation as a whole).
Xanthan is preferably present in a quantity of 0.01 to 0.8% by weight, based on the tooth-cleaning formula-tion as a whole.
Hydroxypropyl-substituted hydrocolloids are prefer-ably present in a quantity of 0.01 to 0.5% by weight, based on the tooth-cleaning formulation as a whole. Pre-ferred representatives are hydroxypropyl guar, hydroxy-propyl cellulose, alginic acid propylene glycol esters or carboxyethyl and carboxymethyl cellulose propylene glycol esters. Accordingly, the propylene glycol function may be attached both by an ether group and by an ester group.
The degree of etherification or esterification per hydro-
4 PCT/EP93/01701 colloid monomer unit is in the usual range of 0.25 toabout 1.
Hydroxypropyl guar and alginic acid propylene glycol ester are particularly preferred, being present in a quantity of 0.01 to 0.5% by weight, based on the tooth-cleaning formulation as a whole.
The ratio by weight of xanthan to hydroxypropyl-substituted hydrocolloid is from 20:1 to 2:1 and prefer-ably from 9:1 to 3:1.
Cationic nitrogen-containing surfactants are, for example, quaternary ammonium compounds, for example cetyl trimethylammonium chloride, dicetyl dimethylammonium chloride or distearyl dimethylammonium chloride.
Ampholytic surfactants are, for example, betaines corresponding to the following general formula:

RlN(CH3)2CH2COO

where R1 is, for example, lauryl, myristyl, cetyl, stearyl, cocoalkyl, tallow alkyl or hydrogenated tallow alkyl, betaines corresponding to the following general formula:

+
R2c(o)NH(cH2)nN(cH3)2cH2coo where R2, for example, may have all the meanings mentioned for Rl and n is an integer of 1 to 6, for example laur-amidopropyl dimethyl betaine or cocoamidopropyl dimethyl betaine.
The betaines are preferably present in a quantity of 0.01 to 1.5% by weight, based on the tooth-cleaning formulation as a whole. Lauramidopropyl betaine and cocoamidopropyl betaine are particularly preferred. N-acyl sarcosinates and N-acyl taurides are also viscosity
5 PCT/EP93/01701 stabilizers in the context of the invention.
In the N-acyl sarcosinates corresponding to the general formula:

R3C(o)N(CH3)CH2Coo-and the N-acyl taurides corresponding to the following general formula:

R4C(o)N(CH3)CH2CH2So3 R3 and R4, for example, may have the meanings mentioned for R1.
Block polymers or statistical copolymers may be used as the polyethylene glycol/propylene glycol copolymers with an average molecular weight of 1,000 to 5,000. The tooth-cleaning formulations preferably contain statisti-cal copolymers which are present in a quantity of 0.02 to 5.0% by weight, based on the tooth-cleaning formulation as a whole.
The mixture of xanthan and the viscosity stabilizer is incorporated in a liquid carrier. The liquid carrier consists of water and moisture-retaining substances, for example polyalcohols such as, for example, glycerol, sorbitol, xylitol, 1,2-propylene glycol or polyethylene glycols with an average molecular weight of 200 to 1,500.
These humectants are present in a quantity of 15 to 85~
by weight, based on the tooth-cleaning formulation as a whole.
Other constituents of the tooth-cleaning formula-tions according to the invention are:

- polishes such as, for example, precipitated and gel silicas which do not themselves make a significant contribution towards thickening, calcium phosphates, 2l4n37~

Wo 94/01080 6 PCT/EP93/01701 polymetaphosphates, aluminium oxide and aluminium hydroxide, the polishes typically being present in a quantity of 10 to 25% by weight, based on the tooth-cleaning formulation as a whole, - solubilizers such as, for example, PEG-30-glycerol monostearic acid ester, PEG-60-glycerol tri(hydroxy-stearic acid) ester, 0 - surfactants, for example anionic surfactants, am-photeric surfactants, nonionic surfactants, prefer-ably sodium laurylsulfate, sodium fatty alcohol ether sulfates, fatty acid glycerol ester sulfate, fatty alcohol EO ethers, fatty alcohol oligosac-charides, - water-soluble fluorine components, for example fluoride and monofluorophosphates, 20 - anti-scale agents, for example phosphonates, prefer-ably azacycloheptane-2,2-diphosphonate, pyrophos-phates (disodium salt or tetrapotassium salt), poly-phosphates (tri- and tetrapolyphosphate), 25 - pH regulators, for example mono-, di-, trialkali metal monophosphates, citrates, - sweeteners, for example saccharine, Acesulfam-K, cyclamate, aspartame, - flavoring oils and plant extracts, for example peppermint oil, spearmint oil, eucalyptus oil, anise oil, fennel oil, caraway oil, menthyl acetate, cinnamic aldehyde, vanillin and thymol and straw-berry, raspberry, pineapple, apple and orange 2140~70 .

flavorings, - microbistatic agents, - and ethanol and dyes.

The liquid tooth-cleaning formulations according to the invention have a viscosity at 25C of around 2,000 to 10,000 and preferably in the range from 5,000 to 8,000 mPa s. They retain their fluidity in the long term, even in the presence of silica abrasives and in conjunction with a high content of humectants. They may be conven-iently dispensed dropwise from a storage container by inverting the container.
The tooth-cleaning formulations according to the invention are applied in liquid form to the bristles of a toothbrush in a quantity of about 1 g so that they may be conventionally used for cleaning teeth. In addition, the tooth-cleaning formulations according to the inven-tion may be used as mouthwashes for rinsing the mouth and throat and also between the teeth. To prepare a mouth-wash, approximately 1 g of the tooth-cleaning formulation according to the invention is added to 20 ml of water.
The following Examples are intended to illustrate the invention without limiting it in any way.

Examples Liquid tooth-cleaning formulations with the follow-ing compositions were prepared.
The tooth-cleaning formulations were kept for 1 hour at 25C in sealed 250 ml screw-top glass bottles, after which their viscosities were measured. The viscosity measurements were carried out with a Brookfield Synchro-Lectric viscosimeter at 25C (type RVF, spindle 3); the ` 21~0370 W0 94/01080 8 PCT/EP93/01701rotational speed was 4 r.p.m.

1. Liquid tooth-cleaning formulation, transParent Glycerol (86%) 35 %
5 Sorbitol (70%) 30 %
Water (deionized) 9.915%
Ethanol (96% by volume) 5.0 %
Polyethylene glycol 400 3.0 %
Precipitated silica (Sident 12 DS)12.0 %
10 Xanthan 0.15 %
Hydroxypropyl guar (Jaguar HP-60)0.05 %
Sodium laurylsulfate 1.5 %
PEG-30-glycerol monostearic acid ester0.5 %
Azacycloheptane-2,2-diphosphonate (Na salt) 1.15 %
15 Sodium fluoride 0.23 %
Saccharine (sodium salt) 0.3 %
Flavoring oil 1.2 %
Dye 0.005%

Viscosity at 25C: 8,000 mPa-s 2. Liquid tooth-cleaninq formulation, opaque Sodium laurylsulfate 1.5 %
Water (deionized) 38.697%
25 Azacycloheptane-2,2-diphosphonic acid1.0 %
Sodium hydroxide 0.315%
Polyethylene glycol 400 2.0 %
Xanthan 0.59 %
Hydroxypropyl guar (Jaguar HP-60)0.06 %
Glycerol (86%) 21.0 %
Sorbitol (70%) 20.0 %
Precipitated silica (Sident 12 DS)12.0 %
Sodium fluoride 0.231%
Titanium dioxide 1.0 %
35 Saccharine (sodium salt) 0.1 %

21403~0 .

Dye 0.07 %
Disodium phosphate 0.5 %
Flavoring oil 1.0 %

Viscosity at 25C: 6,600 mPa-s 3. Liquid tooth-cleaning formulation, transParent Sodium laurylsulfate 1.50 %
PEG-30-glycerol monostearic acid ester 0.5 %
10 Cocoamidopropyl betaine 0.18 %
Disodium phosphate 0.2 %
Water 24.668%
Flavoring oil 1.1 %
Sodium hydroxide 0.315%
15 Ethanol (96% by volume) 5.0 %
Glycerol (86%) 28.38 %
Polyethylene glycol (MW 400)3.0 %
Precipitated silica (Sident 12 DS) 12.0 %
Dye 0.001%
20 Xanthan 0.2 %
Sodium fluoride 0.231%
Sorbitol (70%) 21.7 %
Saccharine (sodium salt) 0.2 %
Azacycloheptane-2,2-diphosphonate 25 (sodium salt) 1.0 %

Viscosity at 25C 9,000 mPa s 4. Liquid tooth-cleaning formulation, opaque 30 Sodium laurylsulfate 1.5 %
Water (deionized) 22.365%
Ucon 75-H-450 (statistical PEG/PPG
copolymer, Union Carbide) 1.0 %
Polyethylene glycol 400 2.0 %
35 Xanthan 0.2 %
Glycerol (86%) 28.0 %

214û370 Sorbitol (70%) 30.0 %
Precipitated silica (Sident 12 DS) 12.0 %
Sodium fluoride 0.23 %
Titanium dioxide 1.0 %
5 Saccharine (sodium salt) 0.2 %
Dye 0 005%
Disodium phosphate 0.50 %
Flavoring oil 1.0 %

Viscosity at 25C: 7,200 mPa-s For use as a dentifrice, approximately 1 g of the tooth-cleaning formulation are applied in liquid form to the bristles of a toothbrush and conventionally used for cleaning teeth.
For use as a mouthwash, approximately 1 g of the tooth-cleaning formulation are dispersed in 20 ml of water.

is present as the viscosity stabilizer in a quantity of 0.1 to 10% by weight.

Claims (5)

1. Water- and humectant-containing tooth-cleaning formulations in the form of a liquid preparation with long-term fluidity and a viscosity of 2,000 to 10,000 and preferably 5,000 to 8,000 mPas at 25°C, xanthan being present as consistency regulator in a quantity of 0.02 to 3.0% by weight and a hydroxypropyl-substituted hydrocol-loid being present as viscosity stabilizer in a quantity of 0.01 to 5.0% by weight.
2. Tooth-cleaning formulations as claimed in claim 1, characterized in that xanthan is present in a quantity of 0.1 to 0.8% by weight.
3. Tooth-cleaning formulations as claimed in claim 1 or 2, characterized in that a hydroxypropyl-substituted hydrocolloid is present in a quantity of 0.01 to 0.5% by weight and is selected from the group consisting of carboxyethyl or carboxymethyl cellulose propylene glycol ester, alginic acid propylene glycol ester, hydroxypropyl cellulose or hydroxypropyl guar.
4. Tooth-cleaning formulations as claimed in claims 1 to 3, characterized in that a hydroxypropyl-substituted hydrocolloid is present in a quantity of 0.01 to 0.5% by weight and is selected from hydroxypropyl guar or alginic acid propylene glycol ester.
5. Tooth-cleaning formulations as claimed in claim 1, characterized in that a combination of the hydroxypropyl-substituted hydrocolloid with a compound from the group consisting of a) nitrogen-containing cationic or ampholytic surfac-tants or b) N-acyl sarcosinates c) N-acyl taurides or d) polyethylene glycol/polypropylene glycol copolymers with an average molecular weight of 1,000 to 5,000
CA002140370A 1992-07-10 1993-07-01 Liquid tooth-cleaning formulations Abandoned CA2140370A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEP4222739.9 1992-07-10
DE4222739A DE4222739A1 (en) 1992-07-10 1992-07-10 Liquid dentifrices

Publications (1)

Publication Number Publication Date
CA2140370A1 true CA2140370A1 (en) 1994-01-20

Family

ID=6462946

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002140370A Abandoned CA2140370A1 (en) 1992-07-10 1993-07-01 Liquid tooth-cleaning formulations

Country Status (10)

Country Link
EP (2) EP0648110B1 (en)
AT (1) ATE142870T1 (en)
CA (1) CA2140370A1 (en)
DE (2) DE4222739A1 (en)
DK (1) DK0648110T3 (en)
ES (1) ES2091622T3 (en)
FI (1) FI950100A0 (en)
GR (1) GR3021175T3 (en)
NO (1) NO943772D0 (en)
WO (1) WO1994001080A2 (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6506366B1 (en) 1998-10-01 2003-01-14 Henkel Kommanditgesellschaft Auf Aktien Liquid tooth cleaning gel
US6682719B2 (en) 2000-04-11 2004-01-27 Henkel Kommanditgesellschaft Auf Aktien Plaque-controlling liquid tooth cleaning agent
JP2007016021A (en) * 2005-06-06 2007-01-25 Meiji Milk Prod Co Ltd Composition for oral cavity care

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995022958A2 (en) * 1994-02-24 1995-08-31 Lingner + Fischer Gmbh Transparent liquid dentifrice
DE19522750A1 (en) * 1995-06-22 1997-01-02 Henkel Kgaa Liquid dentifrices
FR2743494B1 (en) * 1996-01-12 1998-02-06 Rhone Poulenc Chimie AQUEOUS DENTAL COMPOSITION BASED ON A MIXTURE OF XANTHANE GUM AND GUAR GUM AS A THICKENING AGENT
DE19831547A1 (en) * 1998-07-14 2000-01-20 Henkel Kgaa Fluid dentifrice having constant viscosity and good rheological properties, containing humectant, xanthan gum binder and specific type of precipitated silica polishing agent
FR3012333B1 (en) 2013-10-24 2015-11-13 Ouali Razira LIQUID TOOTHPASTE COMPRISING A HYDROLISA OF CHICOREOUS LEAVES, IN PARTICULAR IN THE STADIUM OF ENDIVE
CN111601828B (en) 2017-12-27 2023-03-31 博里利斯股份公司 Ziegler-Natta catalyst and preparation method thereof

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US3506757A (en) 1967-02-06 1970-04-14 Colgate Palmolive Co Liquid dentifrice containing powdered abrasive
GB2082062B (en) * 1980-08-19 1984-07-11 Colgate Palmolive Co Dentifrices containing xanthan and guar gum
GR79663B (en) * 1981-06-26 1984-10-31 Colgate Palmolive Co
US4401648A (en) * 1982-03-29 1983-08-30 Colgate-Palmolive Company Dental cream composition
US4837008A (en) * 1985-04-09 1989-06-06 Peroxydent Group Periodontal composition and method
US4623536A (en) * 1985-06-13 1986-11-18 Church & Dwight Co., Inc. Sodium bicarbonate containing toothpaste
DE3532860C1 (en) * 1985-09-14 1987-03-12 Blendax Werke Schneider Co Oral hygiene products
AU7204787A (en) * 1986-03-17 1987-10-09 Oral Research Laboratories, Inc. Treatment of dental surfaces with plaque retardants
JPH01501472A (en) * 1986-07-11 1989-05-25 オラル、リサーチ、ラボラトリーズ、インコーポレーテッド Composition for prolonging the action of antiplaque agents
JPH0784373B2 (en) * 1986-12-26 1995-09-13 ライオン株式会社 Oral composition
US5073363A (en) * 1989-10-06 1991-12-17 Pellico Michael A Foamable fluoride gels and method

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6506366B1 (en) 1998-10-01 2003-01-14 Henkel Kommanditgesellschaft Auf Aktien Liquid tooth cleaning gel
US6682719B2 (en) 2000-04-11 2004-01-27 Henkel Kommanditgesellschaft Auf Aktien Plaque-controlling liquid tooth cleaning agent
JP2007016021A (en) * 2005-06-06 2007-01-25 Meiji Milk Prod Co Ltd Composition for oral cavity care

Also Published As

Publication number Publication date
NO943772L (en) 1994-10-07
NO943772D0 (en) 1994-10-07
WO1994001080A3 (en) 1994-04-14
EP0648110B1 (en) 1996-09-18
FI950100A (en) 1995-01-09
EP0648110A1 (en) 1995-04-19
DE4222739A1 (en) 1994-01-13
FI950100A0 (en) 1995-01-09
EP0704201A1 (en) 1996-04-03
ATE142870T1 (en) 1996-10-15
GR3021175T3 (en) 1996-12-31
WO1994001080A2 (en) 1994-01-20
DE59303894D1 (en) 1996-10-24
ES2091622T3 (en) 1996-11-01
DK0648110T3 (en) 1997-02-24

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Legal Events

Date Code Title Description
FZDE Discontinued