CN102858310B - There is the most fluorine-containing of high micro efficacy and the dentifrice without anion surfactant - Google Patents
There is the most fluorine-containing of high micro efficacy and the dentifrice without anion surfactant Download PDFInfo
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- 239000004094 surface-active agent Substances 0.000 title claims abstract description 22
- 150000001450 anions Chemical class 0.000 title claims abstract description 20
- 239000011737 fluorine Substances 0.000 title abstract description 14
- 229910052731 fluorine Inorganic materials 0.000 title abstract description 14
- YCKRFDGAMUMZLT-UHFFFAOYSA-N fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title abstract description 13
- 239000000551 dentifrice Substances 0.000 title description 10
- 239000000203 mixture Substances 0.000 claims abstract description 90
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims abstract description 54
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims abstract description 36
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims abstract description 15
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims abstract description 13
- 239000000600 sorbitol Substances 0.000 claims abstract description 13
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 24
- KRHYYFGTRYWZRS-UHFFFAOYSA-M fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 7
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- LNAZSHAWQACDHT-XIYTZBAFSA-N (2R,3R,4S,5R,6S)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2S,3R,4S,5R,6R)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2R,3R,4S,5R,6R)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- CWSZBVAUYPTXTG-UHFFFAOYSA-N 5-[6-[[3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-2-yl]oxymethyl]-3,4-dihydroxy-5-[4-hydroxy-3-(2-hydroxyethoxy)-6-(hydroxymethyl)-5-methoxyoxan-2-yl]oxyoxan-2-yl]oxy-6-(hydroxymethyl)-2-methyloxane-3,4-diol Chemical compound O1C(CO)C(OC)C(O)C(O)C1OCC1C(OC2C(C(O)C(OC)C(CO)O2)OCCO)C(O)C(O)C(OC2C(OC(C)C(O)C2O)CO)O1 CWSZBVAUYPTXTG-UHFFFAOYSA-N 0.000 description 1
- UDMBCSSLTHHNCD-KQYNXXCUSA-N Adenosine monophosphate Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O UDMBCSSLTHHNCD-KQYNXXCUSA-N 0.000 description 1
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- 229940043256 Calcium Pyrophosphate Drugs 0.000 description 1
- JUNWLZAGQLJVLR-UHFFFAOYSA-J Calcium pyrophosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])(=O)OP([O-])([O-])=O JUNWLZAGQLJVLR-UHFFFAOYSA-J 0.000 description 1
- 229940105329 Carboxymethylcellulose Drugs 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N D-sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- NEFBYIFKOOEVPA-UHFFFAOYSA-K Dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
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- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
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- GUBGYTABKSRVRQ-UUNJERMWSA-N Lactose Natural products O([C@@H]1[C@H](O)[C@H](O)[C@H](O)O[C@@H]1CO)[C@H]1[C@@H](O)[C@@H](O)[C@H](O)[C@H](CO)O1 GUBGYTABKSRVRQ-UUNJERMWSA-N 0.000 description 1
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- XAPRFLSJBSXESP-UHFFFAOYSA-N Oxycinchophen Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=C(O)C=1C1=CC=CC=C1 XAPRFLSJBSXESP-UHFFFAOYSA-N 0.000 description 1
- XCOJIVIDDFTHGB-UEUZTHOGSA-N Perillartine Chemical compound CC(=C)[C@H]1CCC(\C=N\O)=CC1 XCOJIVIDDFTHGB-UEUZTHOGSA-N 0.000 description 1
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- UDIPTWFVPPPURJ-UHFFFAOYSA-M Sodium cyclamate Chemical compound [Na+].[O-]S(=O)(=O)NC1CCCCC1 UDIPTWFVPPPURJ-UHFFFAOYSA-M 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- CZMRCDWAGMRECN-GDQSFJPYSA-N Sucrose Natural products O([C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O1)[C@@]1(CO)[C@H](O)[C@@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-GDQSFJPYSA-N 0.000 description 1
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- 239000010642 eucalyptus oil Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
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- 235000019314 gum ghatti Nutrition 0.000 description 1
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- GUBGYTABKSRVRQ-XLOQQCSPSA-N lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- AWLNSWJVBZROPZ-UHFFFAOYSA-N lauramidopropyl betaine Chemical compound CCCCCCCCCCCC(=O)NCCC[N+](N)(N)CC([O-])=O AWLNSWJVBZROPZ-UHFFFAOYSA-N 0.000 description 1
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- 238000004519 manufacturing process Methods 0.000 description 1
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- 239000001525 mentha piperita l. herb oil Substances 0.000 description 1
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- IAYPIBMASNFSPL-UHFFFAOYSA-N oxane Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
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- MSXHSNHNTORCAW-UHFFFAOYSA-M sodium 3,4,5,6-tetrahydroxyoxane-2-carboxylate Chemical compound [Na+].OC1OC(C([O-])=O)C(O)C(O)C1O MSXHSNHNTORCAW-UHFFFAOYSA-M 0.000 description 1
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Abstract
Describing a kind of oral care composition and method, wherein said combination does not contains anion surfactant and fluorine source；Described compositions contains: 15% weight is to the glycerol of 35% weight；17% weight is to the propylene glycol of 45% weight；Sorbitol with 15% weight to 35% weight.
Description
Cross-Reference to Related Applications
This application claims the priority of the U.S. Provisional Patent Application No. 61/299,730 submitted on January 29th, 2010, this application is attached to herein by quoting in full.
Background technology
The present invention relates to oral care composition；More particularly, it relates to do not contain the compositions of fluoride sources and anion surfactant.Described oral care composition contains pH controlling agent and containing glycerol, propylene glycol and the wetting agent system of Sionit.
Fluorine and anion surfactant are the common constituents in oral care composition.Known local uses the oral care composition containing fluorine and anion surfactant to have beneficial effect.Fluoride sources and anion surfactant also have contribution to micro-effect of oral care composition.
Although when in oral care composition by topical application, fluorine and anion surfactant can provide some benefit, but there are still the situation that need not be exposed to fluorine and anion surfactant.For example, the fluorine being exposed to high dose can cause fluorosis.The unfavorable effect being exposed to fluorine and anion surfactant is particularly pertinent in child.
Therefore, being constantly needed to new oral care composition, said composition does not contains fluorine or anion surfactant, and has high micro-effect.
Summary of the invention
In some embodiments, the present invention provides without anion surfactant and the oral care composition of fluorine.In some embodiments, described oral care composition contains glycerol, propylene glycol and Sorbitol.
On the other hand, the method that the present invention includes providing oral health benefits to oral surfaces, the method includes contacting oral surfaces with the oral care composition containing glycerol, propylene glycol, Sorbitol and citric acid, and wherein said oral care composition does not contains anion surfactant and fluoride sources.
Describe in detail
Embodiment of the present invention provide administration and give or use compositions and the method giving people or other animal body.It is therefore preferable that be applied to the specific material of the present invention and compositions pharmaceutically or cosmetically can be accepted." pharmaceutically acceptable " or " the most acceptable " composition here used applies to people and/or animal, treatment needed for providing, sensation, decoration or the interests of beauty treatment and not there is unsuitable adverse side effect (such as toxicity, astringent taste, stimulation and anaphylaxis), and there is rational interests/Hazard ratio.Following definition and unrestriced guidance should take in when reading and explain invention presented here description.
Word used herein above " preferably " and " preferably " refer to provide under certain conditions embodiment of the present invention of certain interests.But, identical or other in the case of, it also may be preferable for other embodiment.Additionally, the description to one or more preferred embodiments is not meant to that other embodiment is useless, more it is not meant to be excluded in outside the scope of the present invention other embodiment.
" oral care composition " used herein above is to be suitable for administration to give or use and give human or animal body, with treatment or prevention oral conditions, or improves the health of human or animal and/or the compositions of appearance.
Term used herein above " dentifrice " refers to be suitable for being administered to give or use giving the paste in oral cavity, glue or liquid preparation.
Unless otherwise stated, all of percent stated of this specification and content should be understood to refer to percetage by weight.The content be given is that weight based on active substance calculates.No matter particular value described herein, refer to the content of each composition, also refers to the further feature of embodiment, all represents that this value adds and subtracts the certain deviation brought due to measurement error.For example, the content of 10% can include 9.5% or 10.5%, and those of ordinary skill in the art is it will be appreciated that measure the error degree brought.Unless otherwise stated, all of measurement is all to carry out under 25 C.
In some embodiments, micro-effect of the most fluorine-containing and oral care composition without anion surfactant is by using the wetting agent system containing glycerol, propylene glycol and Sorbitol to maintain high level.Micro-effect of compositions refers to the ability that said composition tolerant microorganisms grows.A kind of method quick excitation test testing the micro-effect of compositions.The test of this quick excitation provides the EARLY STAGE EVALUATION of the ability of microorganism excitation adjoint to preparation tolerance in controlled manufacture equipment.
Described fast efficacy test (excitation test) is implemented on dentifrice, and to obtain test value, this test value represents the dentifrice tolerance to bacterial growth.In order to prove that dentifrice is effective, mixed cell (Gram-negative and gram-positive cocci) is introduced and reclaims in test product and after different time is spaced.This test measures the kill rate in a period of time and 24 hours interior total kill rates.Result calculates according to standardization region (NAUC) under curve.
Fluoride sources and anion surfactant (such as sodium lauryl sulfate) are the significant contributor of micro-effect of oral care composition.Scope without industrial fluorine and the NAUC value of the dentifrice without anion surfactant is from 17.0 to 30.0.
It is more than 30 according to the value of the NAUC of the oral care composition containing glycerol, propylene glycol and Sorbitol of the present invention.In preferred embodiments, the NAUC value of this oral cavity composition is 65-75 or higher.It is not intended to be limited by any special theory of operation, inventors believe that the high micro efficacy horizontal attribution according to this embodiment is in the low water content of said composition.It addition, the hydrone existed in embodiments is restricted or is difficult to obtain, this growth contributing to suppressing microorganism.Therefore, gross weight based on compositions calculates, and the preferably present composition contains less than 15%, more preferably contains less than 12%, even more preferably contains the water less than 10%.
The content range of the glycerol in described oral care composition can be 10% to 35%, more preferably 17% to 33%, even more preferably 19% to 29%, calculate based on weight.In a preferred embodiment, said composition contains the glycerol of 20% to 24%, calculates based on weight.
The content range of the propylene glycol in described oral care composition can be 15% to 45%, more preferably 19% to 35%, even more preferably 20% to 30%, calculate based on weight.In a preferred embodiment, described compositions contains the propylene glycol of about 25% weight.
The content of the Sorbitol in described oral care composition can be 10% to 35%, more preferably 17% to 30%, even more preferably 28% to 28%, calculate based on weight.In a preferred embodiment, described compositions contains the Sorbitol of about 23% weight.
Present inventors have further discovered that, in there is the most fluorine-containing of the wetting agent system containing glycerol, propylene glycol and Sorbitol and the oral care composition without anion surfactant, add pH controlling agent surprisingly the excitation testing level of said composition is brought up to the level suitable with tradition dentifrice system.
In one embodiment, the content of the pH controlling agent in described oral care composition can be about 0.05% to about 0.2%, calculates based on weight.In a preferred embodiment, described compositions contains the pH controlling agent of about 0.1%.In one embodiment, described pH controlling agent is citric acid.
The NAUC value of 1 is preferably had greater than according to the oral care composition containing pH controlling agent and wetting agent system of the present invention.
The inventors discovered that some solvent of use or alcohol, and/or the use glycerol more than 35% and/or the propylene glycol less than 17% provide and have NAUC less than 50.0, the oral care composition of even less than 30.0, wherein percent calculates based on weight.
The oral care composition of the present invention can also use optional additive, such as those additives being generally used for forming dentifrice, include but not limited to grinding agent and/or amorphous silica gel, other wetting agent, stabilizer, antibacterial, sweeting agent, coloring agent, treatment reagent, caries preventive agent, chelating/sequestering agent, vitamin, aminoacid, protein, antiplaque agent, antilithic, opacifier, antibiotic, antienzyme, enzyme, pH controlling agent, oxidant, antioxidant, brightening agent, primary amino acid (with free alkali form or the form of salt) and other pH controlling agent.
In one embodiment, described oral care composition can include flavoring agent or sweet substance.Any suitable flavoring agent or sweet substance can be used.The suitably example of flavouring ingredients has flavored oils, such as spearmint oil, Fructus Piperis peppermint oil, oil of wintergreen, wiping wood oil, Oleum Caryophylli, sage oil, Eucalyptus oil, Ma Yuelan (marjoram) oil, Oleum Cinnamomi, Fructus Citri Limoniae and orange, and methyl salicylate.Suitably sweeting agent includes sucrose, lactose, maltose, xylitol, sodium sulfinate (sodium
Cyclamate), perillartine, AMP (aspartyl phenyl alanine, methyl ester), saccharin etc..In a suitable case, flavoring agent and sweeting agent can account for about 0.001% to the 5% of compositions or more individually or together, the most each account for 0.1-2.5%.
In certain embodiments, described oral care composition can contain amphion and nonionic surfactant.Zwitterionic surfactant is known in the art, generally includes electric neutrality on the whole, but with the atom/group of at least one positive charge, and the surfactant of the atom/group of at least one negative charge.Preferred zwitterionic surfactant for the present invention is quaternary ammonium compound and glycine betaine, such as amido betaines, such as cocoamidoethyl betaine, cocoamidopropyl, lauramido propyl betaine etc..In some embodiments, the zwitterionic surfactant for the present invention is cocoamidopropyl.
Nonionic surfactant is known in the art, generally includes uncharged surfactant.Preferably nonionic surfactant can be the block copolymer of PULLRONIC F68.Such copolymer nonproprietary name commercially is referred to as poloxamer.This title poloxamer is generally used in combination with numeric suffix and specifies each copolymer.Various Poloxamer can have ethylene oxide and the propylene oxide of different content, which results in poloxamer and has the most multiple chemical constitution and molecular weight.Preferably Poloxamer is Poloxamer 407, BASF, Inc. (Parsippany, N.J.) sell with the trade name of PLURONIC F127.
In different embodiments, described oral care composition can include thickening agent, gel or a combination thereof.The thickening agent and the gel that can be used for the present invention include thickening agent that is inorganic, natural or that synthesize or gel.The example of the thickening agent and gel that can be used for the present invention includes inorganic thickening silica gel, such as amorphous silica gel, such as Zeodent 165 (Huber Corporation), Ireland lichen, iota-carrageenan, tragacanth, polyvinylpyrrolidone, glycerol, natural gum such as tragacanth, gum ghatti, Radix Acaciae senegalis, aluminium-magnesium silicate, sodium alginate, carboxymethyl cellulose, hydroxyethyl cellulose, hydroxypropyl cellulose, hydroxymethyl cellulose, hydroxymethyl carboxypropyl cellulose, methylcellulose, ethyl cellulose, Cellulose sulfate, and the mixture of these compounds and compositions.In certain embodiments, described compositions contains polishing agent, such as the aluminium oxide of silica gel, calcining, sodium bicarbonate, calcium carbonate, dicalcium phosphate or calcium pyrophosphate.
The preferably present composition does not contains alcohol or other solvent, not only due to said composition can be used by child, also as some alcohol and solvent reduces NAUC value.For example, NAUC value is brought down below 47.0 by Polyethylene Glycol (PEG) and/or xylitol.
In different embodiments, the invention provides the method providing oral health benefits to oral surfaces, described method includes contacting the compositions of embodiment of the present invention with oral surfaces.
The embodiment described herein can be further appreciated by by referring to following non-limiting embodiments.
Embodiment
Embodiment
1
Table 1 illustrates a preparation according to embodiment of the present invention.Effect of preparation 1 is through excitation test detection, and gained NAUC value is 88.51.
Table 1 preparation 1
| Composition | Percetage by weight |
| Sionit | 23.0 |
| Glycerol | 20.0 |
| Propylene glycol | 25.0 |
| Saccharin | 0.25 |
| Poloxomer 407 | 2.0 |
| CMC 7MF | 0.5 |
| Zeodent 165 | 10.0 |
| Zeodent 114 | 10.0 |
| Water | 9.0 |
| Flavoring agent | 0.25 |
Embodiment
2
Table 2 illustrates another preparation according to embodiment of the present invention.Effect of preparation 2 is through excitation test detection, and gained NAUC value is 133.31, suitable with the detected value of the traditional dentifrice containing fluoride sources and anion surfactant.
Table 2
| Composition | Percetage by weight |
| Sorbitol | 23.0 |
| Glycerol | 24.0 |
| Propylene glycol | 25.0 |
| Saccharin | 0.25 |
| Poloxomer 407 | 2.0 |
| CMC 7MF | 0.5 |
| Zeodent 165 | 8.0 |
| Zeodent 114 | 8.0 |
| Water | 8.9 |
| Flavoring agent | 0.25 |
| Citric acid | 0.1 |
As following it will be seen that preparation 2 is substantially identical with the preparation 4 in table 3 below, but with the addition of the citric acid (simultaneously reducing the amount of water) of 0.1 wt%.NAUC value is improved to 133.31 by the interpolation of citric acid unexpectedly from 61.31, improves more than twice.
Embodiment
3
Table 3 illustrates a series of preparation according to different embodiments of the present invention.Effect of these preparations is through excitation test detection, and gained NAUC value is more than 50.0.
Table 3
Comparative example
Table 4 illustrates a series of preparations of the contrast embodiment different according to the present invention, and these preparations employ PEG or xylitol, or both it, or the amount of glycerol more than 35 and/or the amount of propylene glycol is less than 17.Some comparative examples also use tetrasodium pyrophosphate (TSPP).Effect of preparation detects through provocation test, and gained NAUC value is less than 50.0.
Table 4
Each patent, application and the printed publication mentioned in this patent document means to be hereby incorporated by through quoting in full.
It will be understood by those skilled in the art that the embodiment described herein can make many changes and modifications without departing from the spirit of the invention.All these changes all fall within the scope of the present invention.
Claims (13)
1. an oral care composition, described compositions contains:
15% weight is to the glycerol of 35% weight；
17% weight is to the propylene glycol of 45% weight；With
15% weight is to the Sorbitol of 35% weight；
Wherein, described compositions does not contains anion surfactant and fluoride sources, and described compositions contains 0.05% weight citric acid to 0.4% weight, and described compositions contains 10% or lesser amount of water.
2. the compositions of claim 1, described compositions contains the citric acid of 0.1% weight.
3. the compositions of claim 1 or 2, described oral care composition contains 18% weight glycerol to 30% weight.
4. the compositions of claim 1 or 2, described oral care composition contains 20% weight glycerol to 25% weight.
5. the compositions of claim 1 or 2, described oral care composition contains 20% weight propylene glycol to 35% weight.
6. the compositions of claim 1 or 2, described oral care composition contains 24% weight propylene glycol to 32% weight.
7. the compositions of claim 1 or 2, described oral care composition contains the propylene glycol of 25% weight.
8. the compositions of claim 1 or 2, described oral care composition contains 18% weight Sorbitol to 28% weight.
9. the compositions of claim 1 or 2, described oral care composition contains the Sorbitol of 23% weight.
10. an oral care composition, described compositions contains:
20% weight is to the glycerol of 24% weight；
The propylene glycol of 25% weight；
The Sorbitol of 23% weight；With
The citric acid of 0.1% weight；And
Wherein, described compositions does not contains anion surfactant and fluoride sources, and described compositions contains 10% or lesser amount of water.
The compositions of 11. claim 10, wherein said compositions has the provocation test value more than 1.
The compositions of 12. claim 10 or 11, described compositions does not contains xylitol or Polyethylene Glycol.
13. according to the purposes in preparing medicine of the compositions any one of aforementioned claim, and described medicine is for treating or prevent oral disease or the patient's condition by being contacted by the oral surfaces of described compositions with main body in need.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US29973010P | 2010-01-29 | 2010-01-29 | |
| US61/299730 | 2010-01-29 | ||
| PCT/US2011/022860 WO2011094494A2 (en) | 2010-01-29 | 2011-01-28 | Fluoride free and anionic surfactant free dentifrice having a high micro efficacy |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN102858310A CN102858310A (en) | 2013-01-02 |
| CN102858310B true CN102858310B (en) | 2016-11-30 |
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ID=
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1232627A (en) * | 1968-06-18 | 1971-05-19 | ||
| CN1190886A (en) * | 1995-06-01 | 1998-08-19 | 科尔加特.帕尔莫利弗公司 | Preparation of a visually clear gel dentifrice |
| ES2137139A1 (en) * | 1998-06-16 | 1999-12-01 | Kin S A Lab | Use of an association of chlorhexidine digluconate and a zinc salt. |
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1232627A (en) * | 1968-06-18 | 1971-05-19 | ||
| CN1190886A (en) * | 1995-06-01 | 1998-08-19 | 科尔加特.帕尔莫利弗公司 | Preparation of a visually clear gel dentifrice |
| ES2137139A1 (en) * | 1998-06-16 | 1999-12-01 | Kin S A Lab | Use of an association of chlorhexidine digluconate and a zinc salt. |
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