WO1991013608A1 - Dentifrice inhibiting dental plaque - Google Patents

Dentifrice inhibiting dental plaque Download PDF

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Publication number
WO1991013608A1
WO1991013608A1 PCT/NO1991/000032 NO9100032W WO9113608A1 WO 1991013608 A1 WO1991013608 A1 WO 1991013608A1 NO 9100032 W NO9100032 W NO 9100032W WO 9113608 A1 WO9113608 A1 WO 9113608A1
Authority
WO
WIPO (PCT)
Prior art keywords
silicone oil
dentifrice
teeth
antibacterial agent
plaque
Prior art date
Application number
PCT/NO1991/000032
Other languages
French (fr)
Inventor
Gunnar Rölla
Jan Eirik Ellingsen
Original Assignee
Roella Gunnar
Ellingsen Jan E
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
Priority to BR919106122A priority Critical patent/BR9106122A/en
Application filed by Roella Gunnar, Ellingsen Jan E filed Critical Roella Gunnar
Priority to US07/930,551 priority patent/US5422098A/en
Priority to DE69110125T priority patent/DE69110125T2/en
Priority to KR1019920702136A priority patent/KR0180243B1/en
Priority to EP91905384A priority patent/EP0518924B1/en
Priority to JP91505211A priority patent/JPH05506846A/en
Priority to CA002077341A priority patent/CA2077341C/en
Priority to SU915053128A priority patent/RU2071315C1/en
Publication of WO1991013608A1 publication Critical patent/WO1991013608A1/en
Priority to NO923471A priority patent/NO178652C/en
Priority to FI923982A priority patent/FI99259C/en
Priority to NO924371A priority patent/NO176627C/en
Priority to GR950402317T priority patent/GR3017204T3/en

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
    • A61K8/30—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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89—Polysiloxanes
    • A61K8/891—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone

Definitions

  • the present invention relates to dentifrices having an improved effect against the growth of plaque on teeth.
  • the dentifrices may be in the form of powders, tooth pastes, chewing gums etc. , but tooth pastes are normally preferred.
  • An important constituent of the dentifrices of the invention is organopolysiloxanes.
  • British Patent No. 789.851 discloses oral hygiene compo ⁇ sitions containing an organopolysiloxane and a higher aliphatic acyl amide of an amino carboxylic acid compound which is preferably a water-soluble carboxylate salt.
  • British Patent No. 1.194.885 describes the addition of a quaternised tertiary cyclic amine in which a Cg_22 aliphatic radical is attached to the quaternary nitrogen atom, to a dimethyl polysiloxane to improve the adherence of the silicone film to the teeth.
  • EP patent application, publication No. 0376363 discloses the use of aminoalkyl silicones and sarcosinate surfactants to prevent staining of teeth and in preventing caries, particularl in conjunction with antimicrobials which have a tendency to stain teeth.
  • Dental plaque consists of dense aggregates of bacteria which attach to the tooth enamel, mainly in the interproximal area, or along the gingival margin.
  • the enamel disintegrates when sucrose or other fermentable carbohydrates are consumed; the plaque bacteria produce organic acids (mainly lactate) in this situation which cause dissolution of the hydroxyapatite of which enamel mainly consists.
  • Dental plaque may also produce enzymes, toxins or antigens which may cause inflammation of the gingival tissue. A chronic inflammation under certain conditio lead to loss of the alveolar bone which supports the teeth, and subsequent toothloss.
  • silicone oil binds to the enamel surfaces of teeth, and provides a hydrophobic surface thereon by forming a thin layer of oil which covers the surface for several hours after a single application.
  • this layer of silicone oil can serve as a reservoir of certain antibacterial agents which are soluble in silicone oil directly or indirectly, after an initial step where the antibacterial agent is dissolved in another organic solvent, and the resultin solution is then dissolved in silicone oil.
  • the invention provides a dentifrice which comprises silicone oil and a fat-soluble antibacterial agent dissolved therein, either directly or after dissolution of the anti ⁇ bacterial agent in an organic solvent.
  • Suitable silicone oils are e.g. the fluid organopolysilo ⁇ xanes described in the above mentioned British Patent No. 789.851.
  • a preferred class comprises the diphenyl or di(C ! _4)alkyl polysiloxanes, in particular liquid dimethylpoly- siloxane.
  • Suitable antibacterial agents are antiseptic phenols, in particular triclosan (also called irgasan) (5-chloro-2- (2 ,4-dichlorophenoxy)phenol) , which may be used in amounts varying from 0.01%, based on the silicone oil, to the maximum amount soluble in the silicone oil.
  • triclosan also called irgasan
  • irgasan 5-chloro-2- (2 ,4-dichlorophenoxy)phenol
  • the antibacterial agent is insoluble in the silicone oil, it may first be dissolved in a suitable organic solvent such as ethanol, and the resulting solution is then dissolved in the silicone oil.
  • the antibacterial agent is non-toxic and is soluble in the silicone oil used and of very limited solubility in water.
  • Triclosan is such an agent and is also known to decrease plaque formation (but not dissolved in polysiloxanes), see e.g. CA. vol 81(1974) no 20897y.
  • the polysiloxane is non-toxic, such as Dow Corning® 200 which has been used in the examples.
  • the silicone oil When the dentifrice is applied to the teeth, the silicone oil forms a hydrophobic layer which serves as a reservoir for the antibacterial agent. As known in the art, the silicone oil in itself will provide some protection due to its hydrophobic character. However we have now found that the protection will be much better when the antibacterial agent is dissolved therein and subsequently slowly released into the environment.
  • the treatment furthermore inhibits calculus formation, probably due to the smooth silicone oil-covered surface which prevents the fixation of calculus to the teeth, and triclosan which inhibits plaque formation. Calculus constitutes in fact calcifi plaque.
  • Fig. 1 illustrates the score for each of the six test persons after painting their teeth with water only.
  • Fig. 2 illustrates the score for the same persons after treatment with dimethylpolysiloxane.
  • Fig. 3 illustrates the score for the same person (-1) after treatment with 0.3 % of triclosan suspended in water.
  • Fig. 4 illustrates the score after treatment with dimethylpolysiloxane containing 0.3% triclosan.
  • the pairs of letters of the right hand side of the graph represent the initials of the test persons, and the subsequent number is the experiment involved.
  • the abscissa indicates the score distribution, and the ordinate represents the number of surfaces having the indicated score for each test person. While triclosan alone gives no improvement, it will be seen that the silicone oil results in an increased number of scores 0 and 1 compared with the control. Silicone oil + 0.3% triclosa gives a marked improvement in plaque scores compared with the control (Fig.l) and the silicone oil treated teeth (Fig.2).

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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)
  • Oral & Maxillofacial Surgery (AREA)
  • Emergency Medicine (AREA)
  • Cosmetics (AREA)
  • Dental Preparations (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)
  • Earth Drilling (AREA)
  • Quick-Acting Or Multi-Walled Pipe Joints (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Laying Of Electric Cables Or Lines Outside (AREA)
  • Electric Cable Installation (AREA)

Abstract

Dentifrice comprising a liquid silicone oil and a fat-soluble antibacterial agent dissolved therein either directly or indirectly after dissolution of the antibacterial agent in an organic solvent. The dentifrice is useful for protection of teeth against plaque formation due to a slow release of the antibacterial agent into the saliva.

Description

"DENTIFRICE INHIBITING DENTAL PLAQUE".
The present invention relates to dentifrices having an improved effect against the growth of plaque on teeth. The dentifrices may be in the form of powders, tooth pastes, chewing gums etc. , but tooth pastes are normally preferred. An important constituent of the dentifrices of the invention is organopolysiloxanes.
From British Patent No. 686.429 it is known to incorporate organopolysiloxanes in dentifrices to prevent the adhesion of or facilitate the removal of tars, stains, tartar and the like from teeth.
British Patent No. 789.851 discloses oral hygiene compo¬ sitions containing an organopolysiloxane and a higher aliphatic acyl amide of an amino carboxylic acid compound which is preferably a water-soluble carboxylate salt. British Patent No. 1.194.885 describes the addition of a quaternised tertiary cyclic amine in which a Cg_22 aliphatic radical is attached to the quaternary nitrogen atom, to a dimethyl polysiloxane to improve the adherence of the silicone film to the teeth.
A similar solution is suggested in US patent 4.161.518 where quaternary ammonium groups are incorporated in an organo- siloxane molecule.
EP patent application, publication No. 0376363 discloses the use of aminoalkyl silicones and sarcosinate surfactants to prevent staining of teeth and in preventing caries, particularl in conjunction with antimicrobials which have a tendency to stain teeth.
Bacterial growth on teeth is a well known problem. The two major dental diseases, caries and periodontitis, are initiated and develop only in the presence of dental plaque. Dental plaque consists of dense aggregates of bacteria which attach to the tooth enamel, mainly in the interproximal area, or along the gingival margin. The enamel disintegrates when sucrose or other fermentable carbohydrates are consumed; the plaque bacteria produce organic acids (mainly lactate) in this situation which cause dissolution of the hydroxyapatite of which enamel mainly consists. Dental plaque may also produce enzymes, toxins or antigens which may cause inflammation of the gingival tissue. A chronic inflammation under certain conditio lead to loss of the alveolar bone which supports the teeth, and subsequent toothloss.
Inhibition of adsorption of bacteria to dental enamel will thus have the potential to prevent both dental caries and periodontal disease. The mecanism by which the bacteria bind to enamel is not well understood. The inhibition of plaque formation obtained up to now has been caused by antibacterial agents with a longterm effect in the mouth. These substances interfere with bacterial growth rather than with the adsorption of bacteria to enamel. Such substances have untoward side effects like staining of teeth and tongue, and unpleasant taste, and they cause a general decrease of the number of bacteria in the oral cavity. Substances which solely reduce the growth of plaque on the teeth by interference with their binding mechanisms have not yet been found.
As it will appear from the above it is previously known that silicone oil binds to the enamel surfaces of teeth, and provides a hydrophobic surface thereon by forming a thin layer of oil which covers the surface for several hours after a single application. We have now surprisingly found that this layer of silicone oil can serve as a reservoir of certain antibacterial agents which are soluble in silicone oil directly or indirectly, after an initial step where the antibacterial agent is dissolved in another organic solvent, and the resultin solution is then dissolved in silicone oil.
Thus, the invention provides a dentifrice which comprises silicone oil and a fat-soluble antibacterial agent dissolved therein, either directly or after dissolution of the anti¬ bacterial agent in an organic solvent.
Suitable silicone oils are e.g. the fluid organopolysilo¬ xanes described in the above mentioned British Patent No. 789.851. A preferred class comprises the diphenyl or di(C!_4)alkyl polysiloxanes, in particular liquid dimethylpoly- siloxane.
Suitable antibacterial agents are antiseptic phenols, in particular triclosan (also called irgasan) (5-chloro-2- (2 ,4-dichlorophenoxy)phenol) , which may be used in amounts varying from 0.01%, based on the silicone oil, to the maximum amount soluble in the silicone oil.
If the antibacterial agent is insoluble in the silicone oil, it may first be dissolved in a suitable organic solvent such as ethanol, and the resulting solution is then dissolved in the silicone oil.
It is important that the antibacterial agent is non-toxic and is soluble in the silicone oil used and of very limited solubility in water. Triclosan is such an agent and is also known to decrease plaque formation (but not dissolved in polysiloxanes), see e.g. CA. vol 81(1974) no 20897y. Similarly it is important that the polysiloxane is non-toxic, such as Dow Corning® 200 which has been used in the examples.
When the dentifrice is applied to the teeth, the silicone oil forms a hydrophobic layer which serves as a reservoir for the antibacterial agent. As known in the art, the silicone oil in itself will provide some protection due to its hydrophobic character. However we have now found that the protection will be much better when the antibacterial agent is dissolved therein and subsequently slowly released into the environment. The treatment furthermore inhibits calculus formation, probably due to the smooth silicone oil-covered surface which prevents the fixation of calculus to the teeth, and triclosan which inhibits plaque formation. Calculus constitutes in fact calcifi plaque.
Experimental
Six students painted their teeth 2 x daily with Q-tips moisted with either water, silicone oil (dimethylpolysiloxane) alone, 0.3 % triclosan in water or silicone oil + 0.3% triclosan. Their teeth were pumiced at the start of the study and plaque was scored on each surface of all the teeth after 4 days. No other form of oral hygiene was allowed. The test persons chewed six pieces of chewing gum containing 75% sucrose per da to increase plaque formation. The results are shown in Fig. 1- 4. Score 0 is given to surfaces with no plaque. Score 1 is given to surfaces where visible plaque is seen on the probe after running the point of the probe along the gingival margin of each tooth. Score 2 indicates visible plaque, and score 3 plaque up to 2 mm above the gingival margin.
Fig. 1 illustrates the score for each of the six test persons after painting their teeth with water only.
Fig. 2 illustrates the score for the same persons after treatment with dimethylpolysiloxane.
Fig. 3 illustrates the score for the same person (-1) after treatment with 0.3 % of triclosan suspended in water.
Fig. 4 illustrates the score after treatment with dimethylpolysiloxane containing 0.3% triclosan.
The pairs of letters of the right hand side of the graph represent the initials of the test persons, and the subsequent number is the experiment involved. The abscissa indicates the score distribution, and the ordinate represents the number of surfaces having the indicated score for each test person. While triclosan alone gives no improvement, it will be seen that the silicone oil results in an increased number of scores 0 and 1 compared with the control. Silicone oil + 0.3% triclosa gives a marked improvement in plaque scores compared with the control (Fig.l) and the silicone oil treated teeth (Fig.2).
The teeth of the group treated with silicone oil + triclosan were shiny clean. Small amounts of plaque occasion¬ ally present was easily removed with a compressed air syringe.
Five individuals who were selected on the basis that they produced high amounts of calculus in their mouths were selected for the study. They used a toothpaste which contained 0,3 % triclosan and silicone oil, and calculus was again scored after one month. The amounts of calculus formed were markedly reduced and the small amount present was easily removed since the calculus was only loosely attached to the teeth.
In an in vitro experiment glass test tubes were treated with either water, silicone oil or silicone oil + 0.3% triclosa 0.5 ml of a 1 day old culture of Strep, utans and 5 ml of glucose broth medium + 5% sucrose was then added to the tubes. Abundant growth and bacteria sticking to the glass wall was seen in the water treated tubes. The tubes treated with silicone oil alone showed reduced growth, only a few bacteria adhering to the glass surface. However, the test tube which had been pretreated with silicone oil containing 0.5% triclosa showed only negligible growth and no bacteria on the glass surface.
These experiments considered together indicate that the teeth and the glasstubes acquire a hydrophobic surface layer with antibaterial activity which inhibit adsorption of bacteri when treated with silicone oil and triclosan. This is a uniqu effect which is not obtained by any previously known clinical procedure in preventive dentistry. It is caused by the fact that the polysiloxane acts as a reservoir for the antibacteria agent (triclosan) dissolved therein. Small amounts of the anti bacterial agent are slowly released from the polysiloxane film adhering to the teeth and will therefore effectively inhibit the formation of plaque due to the limited solubility in water

Claims

C l a i m s
1. Dentifrice comprising a silicone oil, c h a r a c t e r i z e d i n that it comprises a liquid silicone oil and a fat-soluble antibacterial agent dissolved therein either directly or indirectly after dissolution of the antibacterial agent in an organic solvent.
2. Dentifrice according to claim 1, c h a r a c t e r i z e d i n that the liquid silicone oil is a diphenyl or di(C1_4)alkyl-polysiloxane.
3. Dentifrice according to any of claims 1 and 2, c h a r a c t e r i z e d i n that the antibacterial agent iε selected from antiseptic phenols.
4. Dentifrice according to any of claims 1-3 , c h a r a c t e r i z e d i n that the silicone oil is a di-methylpolysiloxane.
5. Dentifrice according to any of claims 1-4, c h a r a c t e r i z e d i n that the antibacterial agent is triclosan (5-chloro-2-(2 ,4-dichlorophenoxy)phenol) .
PCT/NO1991/000032 1990-03-05 1991-03-04 Dentifrice inhibiting dental plaque WO1991013608A1 (en)

Priority Applications (12)

Application Number Priority Date Filing Date Title
JP91505211A JPH05506846A (en) 1990-03-05 1991-03-04 Plaque-inhibiting toothpaste
US07/930,551 US5422098A (en) 1990-03-05 1991-03-04 Dentifrice inhibiting dental plaque
DE69110125T DE69110125T2 (en) 1990-03-05 1991-03-04 TOOTHPASTE AGAINST DENTAL COATING.
KR1019920702136A KR0180243B1 (en) 1990-03-05 1991-03-04 Dentifrice inhibiting dental plaque
EP91905384A EP0518924B1 (en) 1990-03-05 1991-03-04 Dentifrice inhibiting dental plaque
BR919106122A BR9106122A (en) 1990-03-05 1991-03-04 DENTAL PLATE INHIBITOR DENTIFRICIO
CA002077341A CA2077341C (en) 1990-03-05 1991-03-04 Dentifrice inhibiting dental plaque
SU915053128A RU2071315C1 (en) 1990-03-05 1991-03-04 Agent for tooth cleansing
NO923471A NO178652C (en) 1990-03-05 1992-09-04 Dental care based on silicone oil and antiseptic phenol
FI923982A FI99259C (en) 1990-03-05 1992-09-04 Dental plaque reducing tooth cleaner
NO924371A NO176627C (en) 1990-03-05 1992-11-12 Device for retracting and connecting a cable laid on the seabed to a cable connected to an underwater structure
GR950402317T GR3017204T3 (en) 1990-03-05 1995-08-23 Dentifrice inhibiting dental plaque.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
NO90901031A NO901031L (en) 1990-03-05 1990-03-05 BACTERICID COMPOSITION.
NO901031 1990-03-05

Publications (1)

Publication Number Publication Date
WO1991013608A1 true WO1991013608A1 (en) 1991-09-19

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ID=19892952

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/NO1991/000032 WO1991013608A1 (en) 1990-03-05 1991-03-04 Dentifrice inhibiting dental plaque

Country Status (17)

Country Link
US (1) US5422098A (en)
EP (1) EP0518924B1 (en)
JP (1) JPH05506846A (en)
KR (1) KR0180243B1 (en)
AT (1) ATE123216T1 (en)
AU (1) AU646025B2 (en)
BR (1) BR9106122A (en)
CA (1) CA2077341C (en)
DE (1) DE69110125T2 (en)
DK (1) DK0518924T3 (en)
ES (1) ES2075431T3 (en)
FI (1) FI99259C (en)
GR (1) GR3017204T3 (en)
HU (1) HUT63052A (en)
NO (3) NO901031L (en)
RU (1) RU2071315C1 (en)
WO (1) WO1991013608A1 (en)

Cited By (10)

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EP0528457A1 (en) * 1991-08-07 1993-02-24 Unilever N.V. Oral compositions containing an aminosilicone and a lipophilic compound
US5393745A (en) * 1993-12-02 1995-02-28 Schmidt; Alfred Method for treating aphthae using dimethylpolysiloxane
US5607663A (en) * 1994-12-01 1997-03-04 Minnesota Mining And Manufacturing Company Hydrocarbyl containing coatings, compositions and methods of use
US5662887A (en) * 1994-12-01 1997-09-02 Minnesota Mining And Manufacturing Company Fluorocarbon containing coatings, compositions and methods of use
US5866630A (en) * 1993-12-06 1999-02-02 Minnesota Mining And Manufacturing Company Optionally crosslinkable coatings compositions and methods of use
WO2000000024A1 (en) * 1998-06-27 2000-01-06 Trevor Woollard Polydimethylsiloxane containing composition
WO2000000025A1 (en) * 1998-06-27 2000-01-06 Trevor Peter Woollard Germicidal composition
CN1063610C (en) * 1996-02-06 2001-03-28 天津市医药工业技术研究所 Broad-spectrum fungicide
US6312668B2 (en) 1993-12-06 2001-11-06 3M Innovative Properties Company Optionally crosslinkable coatings, compositions and methods of use
WO2002011682A2 (en) * 2000-08-07 2002-02-14 Unilever N.V. Oral composition comprising a silicone and a water-insoluble active agent

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US6280707B1 (en) 1998-12-15 2001-08-28 Dentsply International Inc. Oral prophalaxis paste
GB9922871D0 (en) * 1999-09-28 1999-12-01 Mccormack Limited A novel method for the temporary attenuation of dentine hypersensitivity
US6685921B2 (en) 2000-10-25 2004-02-03 The Procter & Gamble Company Dental care compositions
US7025950B2 (en) 2002-05-09 2006-04-11 The Procter & Gamble Company Oral care compositions comprising dicarboxy functionalized polyorganosiloxanes
US7166235B2 (en) 2002-05-09 2007-01-23 The Procter & Gamble Company Compositions comprising anionic functionalized polyorganosiloxanes for hydrophobically modifying surfaces and enhancing delivery of active agents to surfaces treated therewith
CN102802732B (en) * 2009-09-11 2016-04-27 宝洁公司 For the method and composition of oral surfaces hydrophobically modified
US8992893B2 (en) 2011-04-19 2015-03-31 Arms Pharmaceutical, Llc Method of inhibiting harmful microorganisms and barrier-forming composition therefor
US10426761B2 (en) 2011-04-19 2019-10-01 Arms Pharmaceutical, Llc Method for treatment of disease caused or aggravated by microorganisms or relieving symptoms thereof
BR112015031726A2 (en) 2013-06-24 2017-07-25 Procter & Gamble smudge-proof oral care composition

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GB686429A (en) * 1951-01-09 1953-01-21 Dow Corning Ltd Improvements in or relating to dentifrices
GB789851A (en) * 1952-10-08 1958-01-29 Colgate Palmolive Co Preparations for the care and hygiene of the mouth
US4022880A (en) * 1973-09-26 1977-05-10 Lever Brothers Company Anticalculus composition
EP0161899A2 (en) * 1984-05-09 1985-11-21 Unilever Plc Dentifrice compositions
EP0220890A2 (en) * 1985-10-22 1987-05-06 Beecham Group Plc Oral hygiene composition
EP0371551A2 (en) * 1988-11-28 1990-06-06 Unilever N.V. Dentifrices including modified aminoalkyl silicones
EP0373688A2 (en) * 1988-11-28 1990-06-20 Unilever N.V. Dentifrices containing amino alkyl silicones
EP0376363A1 (en) * 1988-11-28 1990-07-04 Unilever N.V. Dentifrices containing amino alkyl silicones and sarcosinate surfactants

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0528457A1 (en) * 1991-08-07 1993-02-24 Unilever N.V. Oral compositions containing an aminosilicone and a lipophilic compound
US5393745A (en) * 1993-12-02 1995-02-28 Schmidt; Alfred Method for treating aphthae using dimethylpolysiloxane
US6312668B2 (en) 1993-12-06 2001-11-06 3M Innovative Properties Company Optionally crosslinkable coatings, compositions and methods of use
US6596403B2 (en) 1993-12-06 2003-07-22 3M Innovative Properties Company Optionally crosslinkable coatings, compositions and methods of use
US5866630A (en) * 1993-12-06 1999-02-02 Minnesota Mining And Manufacturing Company Optionally crosslinkable coatings compositions and methods of use
US5876208A (en) * 1993-12-06 1999-03-02 Minnesota Mining And Manufacturing Company Optionally crosslinkable coatings for orthodontic devices
US5888491A (en) * 1993-12-06 1999-03-30 Minnesota Mining And Manufacturing Company Optionally crosslinkable coatings, compositions and methods of use
US5662887A (en) * 1994-12-01 1997-09-02 Minnesota Mining And Manufacturing Company Fluorocarbon containing coatings, compositions and methods of use
US5607663A (en) * 1994-12-01 1997-03-04 Minnesota Mining And Manufacturing Company Hydrocarbyl containing coatings, compositions and methods of use
CN1063610C (en) * 1996-02-06 2001-03-28 天津市医药工业技术研究所 Broad-spectrum fungicide
WO2000000025A1 (en) * 1998-06-27 2000-01-06 Trevor Peter Woollard Germicidal composition
WO2000000024A1 (en) * 1998-06-27 2000-01-06 Trevor Woollard Polydimethylsiloxane containing composition
WO2002011682A2 (en) * 2000-08-07 2002-02-14 Unilever N.V. Oral composition comprising a silicone and a water-insoluble active agent
WO2002011682A3 (en) * 2000-08-07 2002-05-16 Unilever Nv Oral composition comprising a silicone and a water-insoluble active agent
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NO178652B (en) 1996-01-29
JPH05506846A (en) 1993-10-07
ES2075431T3 (en) 1995-10-01
DK0518924T3 (en) 1995-10-09
NO924371D0 (en) 1992-11-12
CA2077341A1 (en) 1991-09-06
ATE123216T1 (en) 1995-06-15
FI923982A0 (en) 1992-09-04
HU9202843D0 (en) 1992-11-30
KR0180243B1 (en) 1999-03-20
NO178652C (en) 1996-05-08
NO924371L (en) 1994-05-13
EP0518924A1 (en) 1992-12-23
NO923471D0 (en) 1992-09-04
BR9106122A (en) 1993-03-09
FI99259B (en) 1997-10-15
DE69110125D1 (en) 1995-07-06
AU7343491A (en) 1991-10-10
GR3017204T3 (en) 1995-11-30
CA2077341C (en) 2001-07-24
NO901031D0 (en) 1990-03-05
NO901031L (en) 1991-09-06
FI923982A (en) 1992-09-04
HUT63052A (en) 1993-07-28
NO176627B (en) 1995-01-23
US5422098A (en) 1995-06-06
NO176627C (en) 1999-11-11
NO923471L (en) 1992-09-04
FI99259C (en) 1998-01-26
AU646025B2 (en) 1994-02-03
RU2071315C1 (en) 1997-01-10
EP0518924B1 (en) 1995-05-31
DE69110125T2 (en) 1996-01-25

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