CA1116091A - Malic acid with a bisbiguanide or quaternary ammonium compound as an oral hygiene composition - Google Patents
Malic acid with a bisbiguanide or quaternary ammonium compound as an oral hygiene compositionInfo
- Publication number
- CA1116091A CA1116091A CA324,719A CA324719A CA1116091A CA 1116091 A CA1116091 A CA 1116091A CA 324719 A CA324719 A CA 324719A CA 1116091 A CA1116091 A CA 1116091A
- Authority
- CA
- Canada
- Prior art keywords
- bis
- dihydrochloride
- composition according
- diguanido
- bisbiguanide
- 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.)
- Expired
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
- A61K8/36—Carboxylic acids; Salts or anhydrides thereof
- A61K8/365—Hydroxycarboxylic acids; Ketocarboxylic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
- A61K8/416—Quaternary ammonium compounds
-
- 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
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/43—Guanidines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
- A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
Abstract
ABSTRACT
Oral hygiene compositions useful for controlling dental plaque And gingivitis and for presenting or reducing caries are produced comprising a cationic antimicrobial agent, which can be a bisbiguanide or quaternary ammonium compound, and malic acid as anti-stain agent which reduces the tooth staining effect of the cationic antimicrobial.
Oral hygiene compositions useful for controlling dental plaque And gingivitis and for presenting or reducing caries are produced comprising a cationic antimicrobial agent, which can be a bisbiguanide or quaternary ammonium compound, and malic acid as anti-stain agent which reduces the tooth staining effect of the cationic antimicrobial.
Description
TITLE: Oral Composi.tions The present invention relates to oral hyg:iene compositions useful ~or controllincJ dental plaque and cJi.ngivitis and Eor preven-tiny or red.uci.ng cari.es.
It is known that certain ca-ti.onic antimicrobial ayen-ts are capable of cont.rolling dental plaque and gingivitis and for preventiny or reducing caries when applied regularly to the tecth and oral cavi-ty. Such active agen-ts include certain bisbi~uanides and qua-ternary amMoniuM compounds. ~lowever, -these active insredients have the disadvantaye that they stain or discolour the surfaces of teeth.
For example i-t is known in the art that bisbiyuanides inhibit the formation of plaque and caries (see U.S. Pa-tent No. 1,365,030) and that certain anti-calculus agents may be combined therewith to inhibit the tendency of the bisbiyuanides to stain the ora]. surfaces (see U.S. Patent No. 3,934,002). ~mong the anti-calculus agents disclosed in U.S. Paten-t No. 3,934,002 are quaternary ammonium compounds, zinc phenolsulfonate, hydroxyquinoline, citric acid, lactic acid and pharmaceutically acceptable salts -thereof.
The present invention is based on the surprisiny discovery that malic acid markedly inhibi-ts the stainin~ of .:
tooth surfaces by such bisbiguanides or auaternary ammonium 25 compounds having similar activities. -~
Accordinyly, tne present invention provides an oral hygiene composition, useful for controllins den-tal plaque and ginsivitis and for preventing or reduciny caries which comprises a bisbiguanide or quaternary ammonium compoun~, ' '' ' ' ` ' : ' . " .......... , ' which is capable of con-trolling dental ~laque and ginyivitis and preventiny or reducing caries, and Malic acid.
The amount of bisbiyuanide or quaternary ammoniurn compound may be from 0.01% to about 1.0~ w/w based on the to~al weigh-t of ingredients of the composition or W/V when in li~uid form. s7hen the composi-tion is in the form of a concentrate for dilution before application to the oral acvity, larger amoun-ts of -the ac-tive ingredien-t may be presen-t.
The amount of malic acid may be from 0.1'~ -to 10.0~ w/w or w/v, especially from 0.1% to 1.0%. Likewise, if the composition i.s to be diluted before use, laryer arnounts of malic acid may he present.
The pH of -the composition may be Erom about 5.0 to about 8Ø
The bisbiguanide may be 1,6-bis (2-ethylhexyldiyuanido hexane) dihydrochloride [alexidine dihydrochloride]; 1,6-bis (2-ethylhexyl di~uanido hexane) dihydrofluoride; 1,6-bis (2-ethylhexyl diguanido octane) dihydrochloride; 1,6-bis (2-ethylhexyl diguanido nonane) dihydrochloride; 1,6-bis (2-e-thylhexyl diguanido dodecane) dihydrochloride; or 1,6-di (4-chloropilenyl diguanido hexane) dihydrochloride or the diacetate or digluconate salt thereof. Alexidine dihydrochloride is especially preferred.
The quaternary ammonium compound may be dodecyl dimethyl-(2-phelloxyethyl)-ammoniurn; benzyldimethyl (2-)2-(p-1,3,3-tetramethyl but~il pheno~y)ethyl)ammon:ium; p-bromo-benzyldimethyl-~-(2'-isopro~yl, 4'-chloro, 5'-methyl phenoxy)-pro~yl ar~noniurn; l-hexadecyl-pyridini~n salt;
acylchloamino-formylmethyl pyridinium chloride-iodide com~lex; l~alkyl-4-aminoquinaldinium salt; decamethylene bis(4-aminoquinaldinum chloride) or hexadecamethylene bis (isoquinolinium chloride).
The usual flavouriny ayents, binders, sudsiny agents, humectants, alcohols, frayrances, abrasives and excipients known in the art can be added to the comositions of the present invention.
:.
i1hen the composit:Lon of the present invention is in the form oE a mouthwas11, oral rinse or garyle, -the comDosition is brought i.nto contact ~1ith the oral cavity and then expec-tora-ted. A dose of 15 to 20 rnl. for adults and about lO ml. for children i.s generally sufficient ~hen used on a daily basis, and ~7hen the concen-tration of act:ive bisbiguanide or quaternary ammoni.um compound is in -the range O.Ol -to l.o~ ~i/W or w/v.
I~hen the instant composition is :Ln tl1e form of a clentirice, such as a pas-te, powcler, concentrate, solution or gel :cor direct application to the teeth, it can be used in the normal manner in whic11 a toothpaste i.s used. ~hen the oral composition of the presen-t invention is in a eoneentrate for use with mec11anical irrigation devices sueh as a water jet or "~ater pi]c" ty~e device, approximately lO to 15 ml. should be sprayed into the mouth and circulated in the oral cavity ancl then be expectorated.
~hen the present composition is in the form of a ~reath freshener, ei-ther pump spray or aerosol type, approximately lO to 15 ml. should be sprayecl into the mouth, circulated therethrough and expectorated. When the composi-tion of the present invention is in the form of a troche or a lozenye, it should be allowed to dissolve in the mouth and then be expectorated.
The follo~1ing nonlimitative example more particularly illustrates the present invention.
Ingredients Per cent ~I/y Alexidine Dihydrochloride 0.035 Alcohol USP 15.0 . Glycerin USP lO.0 Flavour 0.4 Sodiurn Saccharin 0.02 Malic Acid 0.382 Buffering Agen-t to pll 5.0-8.0 ~ater USP q.s.
The rnouth~rinse is used in 15 ml. doses for adults to rinse the rnouth and then is expec-torated. For children in the 6 to 12 year old range, l~nl. is the reconlnenc1ec1mouth-rinsing dose.
* Trade Mark : , - .
. :. ' ' :, .
, . , ~ ~,, .
It is known that certain ca-ti.onic antimicrobial ayen-ts are capable of cont.rolling dental plaque and gingivitis and for preventiny or reducing caries when applied regularly to the tecth and oral cavi-ty. Such active agen-ts include certain bisbi~uanides and qua-ternary amMoniuM compounds. ~lowever, -these active insredients have the disadvantaye that they stain or discolour the surfaces of teeth.
For example i-t is known in the art that bisbiyuanides inhibit the formation of plaque and caries (see U.S. Pa-tent No. 1,365,030) and that certain anti-calculus agents may be combined therewith to inhibit the tendency of the bisbiyuanides to stain the ora]. surfaces (see U.S. Patent No. 3,934,002). ~mong the anti-calculus agents disclosed in U.S. Paten-t No. 3,934,002 are quaternary ammonium compounds, zinc phenolsulfonate, hydroxyquinoline, citric acid, lactic acid and pharmaceutically acceptable salts -thereof.
The present invention is based on the surprisiny discovery that malic acid markedly inhibi-ts the stainin~ of .:
tooth surfaces by such bisbiguanides or auaternary ammonium 25 compounds having similar activities. -~
Accordinyly, tne present invention provides an oral hygiene composition, useful for controllins den-tal plaque and ginsivitis and for preventing or reduciny caries which comprises a bisbiguanide or quaternary ammonium compoun~, ' '' ' ' ` ' : ' . " .......... , ' which is capable of con-trolling dental ~laque and ginyivitis and preventiny or reducing caries, and Malic acid.
The amount of bisbiyuanide or quaternary ammoniurn compound may be from 0.01% to about 1.0~ w/w based on the to~al weigh-t of ingredients of the composition or W/V when in li~uid form. s7hen the composi-tion is in the form of a concentrate for dilution before application to the oral acvity, larger amoun-ts of -the ac-tive ingredien-t may be presen-t.
The amount of malic acid may be from 0.1'~ -to 10.0~ w/w or w/v, especially from 0.1% to 1.0%. Likewise, if the composition i.s to be diluted before use, laryer arnounts of malic acid may he present.
The pH of -the composition may be Erom about 5.0 to about 8Ø
The bisbiguanide may be 1,6-bis (2-ethylhexyldiyuanido hexane) dihydrochloride [alexidine dihydrochloride]; 1,6-bis (2-ethylhexyl di~uanido hexane) dihydrofluoride; 1,6-bis (2-ethylhexyl diguanido octane) dihydrochloride; 1,6-bis (2-ethylhexyl diguanido nonane) dihydrochloride; 1,6-bis (2-e-thylhexyl diguanido dodecane) dihydrochloride; or 1,6-di (4-chloropilenyl diguanido hexane) dihydrochloride or the diacetate or digluconate salt thereof. Alexidine dihydrochloride is especially preferred.
The quaternary ammonium compound may be dodecyl dimethyl-(2-phelloxyethyl)-ammoniurn; benzyldimethyl (2-)2-(p-1,3,3-tetramethyl but~il pheno~y)ethyl)ammon:ium; p-bromo-benzyldimethyl-~-(2'-isopro~yl, 4'-chloro, 5'-methyl phenoxy)-pro~yl ar~noniurn; l-hexadecyl-pyridini~n salt;
acylchloamino-formylmethyl pyridinium chloride-iodide com~lex; l~alkyl-4-aminoquinaldinium salt; decamethylene bis(4-aminoquinaldinum chloride) or hexadecamethylene bis (isoquinolinium chloride).
The usual flavouriny ayents, binders, sudsiny agents, humectants, alcohols, frayrances, abrasives and excipients known in the art can be added to the comositions of the present invention.
:.
i1hen the composit:Lon of the present invention is in the form oE a mouthwas11, oral rinse or garyle, -the comDosition is brought i.nto contact ~1ith the oral cavity and then expec-tora-ted. A dose of 15 to 20 rnl. for adults and about lO ml. for children i.s generally sufficient ~hen used on a daily basis, and ~7hen the concen-tration of act:ive bisbiguanide or quaternary ammoni.um compound is in -the range O.Ol -to l.o~ ~i/W or w/v.
I~hen the instant composition is :Ln tl1e form of a clentirice, such as a pas-te, powcler, concentrate, solution or gel :cor direct application to the teeth, it can be used in the normal manner in whic11 a toothpaste i.s used. ~hen the oral composition of the presen-t invention is in a eoneentrate for use with mec11anical irrigation devices sueh as a water jet or "~ater pi]c" ty~e device, approximately lO to 15 ml. should be sprayed into the mouth and circulated in the oral cavity ancl then be expectorated.
~hen the present composition is in the form of a ~reath freshener, ei-ther pump spray or aerosol type, approximately lO to 15 ml. should be sprayecl into the mouth, circulated therethrough and expectorated. When the composi-tion of the present invention is in the form of a troche or a lozenye, it should be allowed to dissolve in the mouth and then be expectorated.
The follo~1ing nonlimitative example more particularly illustrates the present invention.
Ingredients Per cent ~I/y Alexidine Dihydrochloride 0.035 Alcohol USP 15.0 . Glycerin USP lO.0 Flavour 0.4 Sodiurn Saccharin 0.02 Malic Acid 0.382 Buffering Agen-t to pll 5.0-8.0 ~ater USP q.s.
The rnouth~rinse is used in 15 ml. doses for adults to rinse the rnouth and then is expec-torated. For children in the 6 to 12 year old range, l~nl. is the reconlnenc1ec1mouth-rinsing dose.
* Trade Mark : , - .
. :. ' ' :, .
, . , ~ ~,, .
Claims (7)
IS CLAIMED ARE DEFINED AS FOLLOWS:
1. An oral hygiene composition, useful for controlling dental plaque and gingivitis and for preventing or reducing caries which comprises from 0.01% to 1% w/w or w/v of a bisbiguanide or quaternary ammonium compound, which is capable of controlling dental plaque and gingivitis and preventing or reducing caries, and from 0.1% to 10% w/w or w/v of malic acid, the composition having a pH of from substantially 5.0 to 8Ø
2. A composition according to claim 1, wherein the amount of malic acid is from 0.1% to 1.0% w/w or w/v.
3. A composition according to claim 1, characterised in that a bisbiguanide is present and is one of 1,6-bis (2-ethylhexyl diguanido hexane) dihydrochloride;
1,6-bis (2-ethylhexyl diguanido hexane) dihydrofluoride, 1,6-bis (2-ethylhexyl diguanido octane) dihydrochloride; 1,6-bis (2-ethylhexyl diguanido nonane) dihydrochloride; or 1,6-di (4-chlorophenyl diguanido hexane) dihydrochloride or the diacetate or digluconate salt thereof.
1,6-bis (2-ethylhexyl diguanido hexane) dihydrofluoride, 1,6-bis (2-ethylhexyl diguanido octane) dihydrochloride; 1,6-bis (2-ethylhexyl diguanido nonane) dihydrochloride; or 1,6-di (4-chlorophenyl diguanido hexane) dihydrochloride or the diacetate or digluconate salt thereof.
4. A composition according to claim 1, characterised in that a quaternary ammonium compound is present and is one of dodecyl dimethyl-(2-phenoxy-ethyl)-ammonium; benzyldimethyl(2-)2-(p-1,3,3-tetramethyl butyl phenoxy) ethoxyl) ethyl)ammonium; p-bromobenzyl-dimethyl-.gamma.-(2'-isopropyl,4'-chloro,5'-methyl phenoxy)-propyl ammonium; l-hexadecyl-pyridinium salt; acylcholaminoformyl-methyl pyridinium chloride-iodide complex; l-alkyl-4-amino-quinaldinium salt;
decamethylene bis(4-aminoquinaldinium chloride) or hexadecamethylene bis (isoquinolinium chloride).
decamethylene bis(4-aminoquinaldinium chloride) or hexadecamethylene bis (isoquinolinium chloride).
5. A composition according to claim 4, characterised in that the antimi-crobial agent is 1,6-bis (2-ethylhexyl diguanido hexane) dihydrochloride.
6. A composition according to any one of claims 1, 2 or 3 in the form of a mouthwash, oral rinse, dentifrice, toothpowder, aerosol, troche or lozenge, gel, or in a form suitable for dispensing through a water jet.
7. A composition according to any one of claims 4 and 5, in the form of a mounthwash, oral rinse, dentifrice, toothpowder, aerosol, troche or lozenge, gel, or in a form suitable for dispensing through a water jet.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US892,276 | 1978-03-31 | ||
| US05/892,276 US4183916A (en) | 1978-03-31 | 1978-03-31 | Oral compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1116091A true CA1116091A (en) | 1982-01-12 |
Family
ID=25399700
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA324,719A Expired CA1116091A (en) | 1978-03-31 | 1979-03-30 | Malic acid with a bisbiguanide or quaternary ammonium compound as an oral hygiene composition |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4183916A (en) |
| EP (1) | EP0004719A3 (en) |
| AU (1) | AU523448B2 (en) |
| CA (1) | CA1116091A (en) |
| DK (1) | DK134179A (en) |
| NZ (1) | NZ190031A (en) |
| ZA (1) | ZA791531B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4961923A (en) * | 1988-02-19 | 1990-10-09 | Dentsply Management Corp. | Irrigants for use in scaling and/or lavage apparatus |
| US6190642B1 (en) | 1988-02-19 | 2001-02-20 | Dentsply Research & Development Corp. | Irrigating and lavage compositions |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USRE31397E (en) * | 1978-03-31 | 1983-09-27 | Beecham Inc. | Oral compositions |
| US4267164A (en) * | 1980-01-31 | 1981-05-12 | Block Drug Company Inc. | Effervescent stannous fluoride tablet |
| US4323551A (en) * | 1981-02-19 | 1982-04-06 | The Procter & Gamble Company | Mouthwash compositions |
| EP0110568A1 (en) * | 1982-10-29 | 1984-06-13 | The Procter & Gamble Company | Oral compositions |
| US4521403A (en) * | 1983-01-20 | 1985-06-04 | Simon Gilbert I | Chemotherapeutic method for treating periodontal disease |
| US4567036A (en) * | 1983-12-30 | 1986-01-28 | Simon Gilbert I | Chemotherapeutic method for treating periodontal disease, and composition therefore |
| GB8625103D0 (en) * | 1986-10-20 | 1986-11-26 | Unilever Plc | Disinfectant compositions |
| US5948390A (en) * | 1997-08-25 | 1999-09-07 | Pfizer Inc. | Stable zinc/citrate/CPC oral rinse formulations |
| US6121213A (en) * | 1998-07-28 | 2000-09-19 | Block Drug Company, Inc. | Stable peroxide denture paste |
| CA2355293C (en) | 1998-12-23 | 2005-08-16 | Orphan Medical, Inc. | Microbiologically sound and stable solutions of gamma-hydroxybutyrate salt for the treatment of narcolepsy |
| WO2001070178A2 (en) | 2000-03-23 | 2001-09-27 | Dentsply International Inc. | Tooth whitening composition |
| US6685923B2 (en) | 2001-01-25 | 2004-02-03 | Dentsply Research & Development Corp. | Tooth whitening material and method of whitening teeth |
| US20030108846A1 (en) * | 2001-12-06 | 2003-06-12 | Kimberly-Clark Worldwide, Inc. | Disposable oral hygiene device and methods of making same |
| US9241885B2 (en) * | 2004-01-29 | 2016-01-26 | The Procter & Gamble Company | Oral care compositions comprising increased bioavailable levels of quaternary ammonium antimicrobials |
| CN1314384C (en) * | 2004-11-22 | 2007-05-09 | 南方医科大学 | Oral cavity nursing agent |
| BR112019002366B1 (en) | 2016-08-11 | 2022-11-29 | Colgate-Palmolive Company | COMPOSITION FOR ORAL HYGIENE, METHOD TO MANUFACTURE THE SAID AND METHOD TO TREAT AND/OR INHIBIT CHEMICAL STAINS, DENTAL EROSION, GINGIVAL DISEASE, HALITOSIS AND/OR BIOFILM FORMATION |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3124506A (en) * | 1964-03-10 | Compositions containing lactic acid | ||
| US1275275A (en) * | 1915-06-19 | 1918-08-13 | Samuel Levinston | Mouth toilet preparation. |
| NL106944C (en) * | 1958-10-31 | |||
| US3937805A (en) * | 1971-11-10 | 1976-02-10 | Colgate-Palmolive Company | Method of making dentifrice compositions containing insolubilized salts of 1,6-di-(p-chlorophenyl biguanido) hexane |
| US3934002A (en) * | 1972-06-30 | 1976-01-20 | The Procter & Gamble Company | Oral compositions for plaque, caries and calculus retardation with reduced staining tendencies |
| GB1365030A (en) * | 1972-11-30 | 1974-08-29 | Merck & Co Inc | Oral compositions |
| CH590659A5 (en) * | 1973-01-20 | 1977-08-15 | Blendax Werke Schneider Co | |
| US3937807A (en) * | 1973-03-06 | 1976-02-10 | The Procter & Gamble Company | Oral compositions for plaque, caries, and calculus retardation with reduced staining tendencies |
| US3925543A (en) * | 1973-11-01 | 1975-12-09 | Colgate Palmolive Co | Antibacterial oral compositions containing preservative-antioxidants |
| US3887701A (en) * | 1974-11-01 | 1975-06-03 | Colgate Palmolive Co | Antibacterial oral compositions containing preservative-antioxidants |
| US4051234A (en) * | 1975-06-06 | 1977-09-27 | The Procter & Gamble Company | Oral compositions for plaque, caries, and calculus retardation with reduced staining tendencies |
| US4067962A (en) * | 1975-08-01 | 1978-01-10 | The Procter & Gamble Company | Oral compositions containing trifluoromethyl phenyl bis-biguanides as antiplaque agents |
| JPS5822009B2 (en) * | 1976-02-07 | 1983-05-06 | 藤沢薬品工業株式会社 | Method for removing bitterness from oral chlorhexidine preparations |
| US4080441A (en) * | 1976-12-27 | 1978-03-21 | Colgate-Palmolive Company | Antibacterial oral composition |
| DE2722187A1 (en) * | 1977-05-17 | 1978-11-23 | Colgate Palmolive Co | Buccal hygiene composition or dentifrice - contains a nitrogen-contg. germicide and a water-soluble polyamino-polyphosphonic acid or its salts |
-
1978
- 1978-03-31 US US05/892,276 patent/US4183916A/en not_active Ceased
-
1979
- 1979-03-19 EP EP79300425A patent/EP0004719A3/en not_active Withdrawn
- 1979-03-28 NZ NZ190031A patent/NZ190031A/en unknown
- 1979-03-30 AU AU45560/79A patent/AU523448B2/en not_active Ceased
- 1979-03-30 ZA ZA791531A patent/ZA791531B/en unknown
- 1979-03-30 DK DK134179A patent/DK134179A/en not_active Application Discontinuation
- 1979-03-30 CA CA324,719A patent/CA1116091A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4961923A (en) * | 1988-02-19 | 1990-10-09 | Dentsply Management Corp. | Irrigants for use in scaling and/or lavage apparatus |
| US6190642B1 (en) | 1988-02-19 | 2001-02-20 | Dentsply Research & Development Corp. | Irrigating and lavage compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| NZ190031A (en) | 1981-03-16 |
| EP0004719A3 (en) | 1979-10-31 |
| EP0004719A2 (en) | 1979-10-17 |
| ZA791531B (en) | 1980-04-30 |
| AU523448B2 (en) | 1982-07-29 |
| US4183916A (en) | 1980-01-15 |
| AU4556079A (en) | 1979-10-04 |
| DK134179A (en) | 1979-10-01 |
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