CN102961754A - Beta-cyclodextrin calcium carbonate microsphere drug loading system as well as preparation method and application thereof - Google Patents
Beta-cyclodextrin calcium carbonate microsphere drug loading system as well as preparation method and application thereof Download PDFInfo
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- CN102961754A CN102961754A CN201210532284XA CN201210532284A CN102961754A CN 102961754 A CN102961754 A CN 102961754A CN 201210532284X A CN201210532284X A CN 201210532284XA CN 201210532284 A CN201210532284 A CN 201210532284A CN 102961754 A CN102961754 A CN 102961754A
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Abstract
The invention discloses a beta-cyclodextrin calcium carbonate microsphere drug loading system which comprises 20-95% of beta-cyclodextrin calcium carbonate microsphere and 5-80% of active ingredients. Moreover, the invention provides a preparation method of the beta-cyclodextrin calcium carbonate microsphere and a preparation method of a drug loading beta-cyclodextrin calcium carbonate microsphere which is applied to the field of oral care. According to the drug loading beta-cyclodextrin calcium carbonate microsphere, the bad odor of the drugs is overcome, the irritation of the drugs is reduced, the effect of efficiently cleaning the oral cavities is achieved and the aim of remaining the active ingredients for a long time is realized.
Description
Technical field
The invention belongs to household chemicals field, relate to a kind of beta-schardinger dextrin-calcium carbonate microspheres medicine-carried system and its preparation method and application.
Background technology
That calcium carbonate is that occurring in nature exists is the abundantest, one of biogenic mineral material the most widely, has special mechanical performance, optical property and complicated pattern.Can make respectively ground calcium carbonate and precipitated calcium carbonate by physical method and chemical method at present.Comprise carbonizatin method, precipitation method and gaseous diffusion process in the chemical preparation process.The carbanion that wherein precipitation method utilizes calcium ion that water-soluble Ca salt provides and carbonate to provide reacts under optimum conditions Direct precipitation and generates calcium carbonate, simple to operate, the conditions such as reactant concentration, reaction temperature, mineralising time can control to obtain required crystalline structure flexibly, so range of application is wider.The characteristics such as calcium carbonate is simple because of its production technology, environmental friendliness is pollution-free, at rubber, plastics, printing ink and coatings industry, and important function has been brought into play in the field such as papermaking, health product.
The characteristics such as calcium carbonate is a kind of important inorganic material and typical biogenic mineral, and is simple because of its production technology, that environmental friendliness is pollution-free are widely used in the industries such as plastics, papermaking, printing ink, coating, weaving, binding agent, cosmetics, food.Be one of filler of large usage quantity in the rubber industry such as calcium carbonate, not only can increase the volume of rubber product, can also significantly improve tensile strength, tearing strength, the wearability of product itself, significant strengthening action is arranged.In recent years, along with the development of artificial bionic synthetic calcium carbonate technology and process for modifying surface, the using value of calcium carbonate also is greatly improved.
Beta-schardinger dextrin-is to have 71, and the cyclic oligosaccharide of-4 glucose units, space structure are up big and down small slightly tapered cylinders, and the molecule outside is hydrophilic, and is inboard hydrophobic.Because its its unique structure, beta-schardinger dextrin-can wrap and connect multiple guest molecule, and very similar enzyme is called as molecular capsule to the identification of substrate.Because beta-schardinger dextrin-can increase drug solubility, strengthen medicine stability, the regulating drug rate of release is covered bad smell, therefore is widely used in the fields such as medicine, food, cosmetics.
The medicine controlled releasing technology comprises reservoir devices (film control type), matrix type (matrix type), microcapsule and particle type at present.Reservoir devices is a class dosage form that is enclosed with the polymeric membrane of control drug release rate in the Drug Storage periphery.Matrix type then directly is dispersed in medicine in the skeleton of macromolecular material formation, and two kinds of methods all can reduce the peak valley toxic and side effects of medicine, is difficult for causing the drug accumulation poisoning, increases Drug therapy stability, improves curative effect.Microcapsule and particle type controlled release preparation can be regarded microminiaturized depot formulation and skeleton preparation as, and be big or small below 1mm, more general only 0.1 μ m or tens of micron.Therefore microcapsule and microspheric not only possess the advantage of reservoir devices and matrix type, and particle volume is little, by molecule carrying medicament like this, can more accurate control drug loading amount, and fixed point achieves the goal and discharges the position, reaches drug release regularly, orientation, the function of location.
Use precipitation method artificial bionic synthetic calcium carbonate, by effective production control condition, and in building-up process, add beta-schardinger dextrin-, the calcium carbonate micro structure is combined with beta-schardinger dextrin-, prepare the beta-schardinger dextrin-calcium carbonate microspheres.The calcium carbonate microparticle that obtains under suitable preparation technology has regular spherical, and spherical surface is coarse, and whole system has enough large surface area.And the molecular capsule beta-schardinger dextrin-that its microsphere surface is included, the surface area that can utilize calcium carbonate fully with Oleum Folium Artemisiae Argyi, Cortex Cinnamomi wet goods medicament contact and with the medicine parcel wherein, the while medicines structure is unaffected.With this load system for the preparation of oral care product; under the acid condition of oral cavity, calcium carbonate and beta-schardinger dextrin-all can slowly effectively be degraded, thereby the clathrate Chinese medicine is progressively discharged; effectively the prolong drug effectiveness time, protect for a long time oral environment.At present, about beta-schardinger dextrin-with calcium carbonate combines and the advantage of carrying medicament is not still fully excavated, report very rarely, and the application of such medicine-carried system is restricted especially.
Summary of the invention
The beta-schardinger dextrin-space structure is up big and down small slightly tapered cylinder, and the molecule outside is hydrophilic, and is inboard hydrophobic.Borrow the Van der Waals force drug molecule that some size and shapes are suitable to be contained in the circulus, form the outer field macromole of ultra micro cryptomere clathrate.By this clathration, not only can increase drug solubility, increase the stability of medicine, and can cover the adverse drug abnormal smells from the patient, reduce poisonous side effect of medicine, regulate drug release rate, improve bioavailability.Various plants quintessence oil and natural extracts have the effects such as antiinflammatory, antiallergic, raising are immune, antibiotic, analgesia, spasmolytic, antioxidation, emesis, but volatile, easily oxidized, their application that had the drawbacks limit such as bad smell.Just the said medicine shortcoming can be overcome by beta-schardinger dextrin-calcium carbonate microspheres system carrying medicament, also medicine irritation can be effectively reduced simultaneously.
Purpose of the present invention is providing a kind of medicine carrying beta-schardinger dextrin-calcium carbonate microspheres, comprises by weight percentage following composition:
Beta-schardinger dextrin-calcium carbonate microspheres 20-95%;
Active component 5-80%.
The preferred little 50-85% of beta-schardinger dextrin-calcium carbonate, active component 15%-50%.
Described active component comprises thymol, Mentholum, tea polyphenols, Oleum Caryophylli, wintergreen oil, eucalyptus oil, Oleum Folium Artemisiae Argyi, Oleum Cinnamomi, tea tree ethereal oil, Oleum lavandula angustifolia, Fructus Citri Limoniae oil, litsea cubeba oil, citronella oil, patchouli oil, perilla oil, Fructus Zanthoxyli oil, the Flos Pelargonii quintessence oil, the gin quintessence oil, Radix Oenotherae erythrosepalae quintessence oil, Oleum Vitis viniferae, Herba Origani oil, Flos Rosae Rugosae quintessence oil, Aloe powder, flavone extract, the curcumin extract, anthrone Anthraquinones extract, in organic acid and the alkaloids extract one or more.
Provide in addition a kind of preparation method of beta-schardinger dextrin-calcium carbonate microspheres to comprise following steps:
A) configuration sodium carbonate liquor adds beta-schardinger dextrin-to fully dissolving, obtains the beta-schardinger dextrin-sodium carbonate liquor,
B) under agitation, fast the beta-schardinger dextrin-sodium carbonate liquor is joined in the calcium chloride solution with the corresponding molar concentration of sodium carbonate liquor of step in a),
C) leave standstill, centrifugal, drying.
D) with step c) the beta-schardinger dextrin-calcium carbonate microspheres of gained adds and contains in the solution of active constituents of medicine, and vibrations are stirred,
E) dry for standby.
The molar concentration of described sodium carbonate liquor is 50mM-150mM, and the molar concentration of the beta-schardinger dextrin-in the described beta-schardinger dextrin-sodium carbonate liquor is 0.1mM-10mM.
The molar concentration of described sodium carbonate liquor is 50mM, 100mM or 150mM, and the molar concentration of the beta-schardinger dextrin-in the described beta-schardinger dextrin-sodium carbonate liquor is 0.1mM, 1mM or 10mM.
Described stirring condition is 4-70 ℃, and mixing speed is 300-900rpm, and the rear mixing time that feeds intake is controlled at 30 minutes.
Described stirring condition is 25 or 40 ℃, and mixing speed is 600 or 900rpm, and the rear mixing time that feeds intake is controlled at 10 minutes.
A kind of oral care product is provided in addition, has comprised the medicine-carried system of described beta-schardinger dextrin-calcium carbonate microspheres.
Described oral care product is preferably chewing gum or toothpaste.
The present invention will obtain following income:
1. in conjunction with structural advantages and the range of application thereof of calcium carbonate and beta-schardinger dextrin-, thus design and prepare a kind of beta-schardinger dextrin-calcium carbonate microspheres.
2. investigated above-mentioned microsphere as the potentiality of drug loading system, the result shows that this medicine-carried system load efficiency is high, drug release is thorough.
3. said medicine load system is applied to the preparation of specific product, has further confirmed its practicality.
4. use the newtype drug load system that the present invention relates to and prepare a kind of safely and effectively oral care product, this product combines the advantage of traditional oral care product, the forgone shortcoming of traditional oral care product has realized making the purpose of the long-acting retention of active component when reaching the high-efficiency cleaning oral cavity.
5. can cover the adverse drug abnormal smells from the patient, reduce poisonous side effect of medicine, regulate drug release rate, improve bioavailability.
Description of drawings
Fig. 1 uses calcium carbonate 100mM-beta-schardinger dextrin-0.1mM, reacts the Electronic Speculum figure of resulting calcium carbonate microspheres.
Fig. 2 uses calcium carbonate 100mM-beta-schardinger dextrin-1mM, reacts the Electronic Speculum figure of resulting calcium carbonate microspheres.
Fig. 3 uses calcium carbonate 100mM-beta-schardinger dextrin-10mM, reacts the Electronic Speculum figure of resulting calcium carbonate microspheres.
Fig. 4 uses calcium carbonate 150mM-beta-schardinger dextrin-0.1mM, reacts the Electronic Speculum figure of resulting calcium carbonate microspheres.
Fig. 5 uses calcium carbonate 150mM-beta-schardinger dextrin-1mM, reacts the Electronic Speculum figure of resulting calcium carbonate microspheres.
Fig. 6 uses calcium carbonate 150mM-beta-schardinger dextrin-10mM, reacts the Electronic Speculum figure of resulting calcium carbonate microspheres.
Fig. 7 uses the drug release curve chart of dry medicine carrying beta-schardinger dextrin-calcium carbonate microspheres in artificial saliva that is loaded with wintergreen oil, eucalyptus oil, Oleum Folium Artemisiae Argyi, Oleum Caryophylli (according to mass ratio 1/3/2/2).
Specific embodiment
The preparation of beta-schardinger dextrin-calcium carbonate microspheres
Prepare the sodium carbonate liquor of different molar concentrations (50mM-150mM), the beta-schardinger dextrin-that adds the certain mass ratio is stirred to fully dissolving (0.1mM-10mM), under stirring, 4 ℃-70 ℃, 300-900 rpm fast mentioned solution is added in the calcium chloride solution of corresponding molar concentration, leave standstill 10min-60min, centrifugal three times of centrifugal rear repetition pure water rinsing, drying.Metal spraying thermal field scanning electron microscopic observation pattern.
Embodiment 1
The preparation molar concentration is the sodium carbonate liquor of 100mM, and making beta-schardinger dextrin-concentration after the adding cyclodextrin is stirred to and dissolves fully is 0.1mM.Under 25 ℃, 600 rpm stir, mentioned solution is added in the calcium chloride solution of corresponding molar concentration (10mM) fast, leave standstill 30min, centrifugal three times of centrifugal rear repetition pure water rinsing, drying.Metal spraying thermal field scanning electron microscopic observation pattern, as shown in Figure 1.
The preparation molar concentration is the sodium carbonate liquor of 100mM, and it is 1mM that the adding beta-schardinger dextrin-is stirred to the rear beta-schardinger dextrin-concentration of fully dissolving.Under 25 ℃, 600 rpm stir, mentioned solution is added in the calcium chloride solution of corresponding molar concentration (100mM) fast, leave standstill 30min, centrifugal three times of centrifugal rear repetition pure water rinsing, drying.Metal spraying thermal field scanning electron microscopic observation pattern, as shown in Figure 2.
The preparation molar concentration is the sodium carbonate liquor of 100mM, and it is 10mM that the adding beta-schardinger dextrin-is stirred to the rear beta-schardinger dextrin-concentration of fully dissolving.Under 25 ℃, 600 rpm stir, mentioned solution is added in the calcium chloride solution of corresponding molar concentration (100mM) fast, leave standstill 30min, centrifugal three times of centrifugal rear repetition pure water rinsing, drying.Metal spraying thermal field scanning electron microscopic observation pattern, as shown in Figure 3.
Embodiment 4
The preparation molar concentration is the sodium carbonate liquor of 150mM, and it is 0.1mM that the adding beta-schardinger dextrin-is stirred to the rear beta-schardinger dextrin-concentration of fully dissolving.Under 25 ℃, 600 rpm stir, mentioned solution is added in the calcium chloride solution of corresponding molar concentration (100mM) fast, leave standstill 30min, centrifugal three times of centrifugal rear repetition pure water rinsing, drying.Metal spraying thermal field scanning electron microscopic observation pattern, as shown in Figure 4.
Embodiment 5
The preparation molar concentration is the sodium carbonate liquor of 150mM, and it is 1mM that the adding beta-schardinger dextrin-is stirred to the rear beta-schardinger dextrin-concentration of fully dissolving.Under 25 ℃, 600 rpm stir, mentioned solution is added in the calcium chloride solution of corresponding molar concentration (100mM) fast, leave standstill 30min, centrifugal three times of centrifugal rear repetition pure water rinsing, drying.Metal spraying thermal field scanning electron microscopic observation pattern, as shown in Figure 5.
Embodiment 6
The preparation molar concentration is the sodium carbonate liquor of 150mM, and it is 10mM that the adding beta-schardinger dextrin-is stirred to the rear beta-schardinger dextrin-concentration of fully dissolving.Under 25 ℃, 600 rpm stir, mentioned solution is added in the calcium chloride solution of corresponding molar concentration (100mM) fast, leave standstill 30min, centrifugal three times of centrifugal rear repetition pure water rinsing, drying.Metal spraying thermal field scanning electron microscopic observation pattern, as shown in Figure 6.
Medicine carryingβ-
The preparation of cyclodextrin calcium carbonate microspheres
Get the beta-schardinger dextrin-calcium carbonate microspheres of an amount of drying, be impregnated in the soybean oil saturated solution of the liquid essential oil of reasonable recipe or solid effective ingredient, stir vibrations 48h, microsphere surface is fully contacted with quintessence oil.After micro-ball load reached capacity, filtering solution took out medicine carrying cyclodextrin calcium carbonate granule, and oven dry is for subsequent use naturally.
Embodiment 7
Get the dry beta-schardinger dextrin-calcium carbonate microspheres of 100g, get 50g wintergreen oil, 150g eucalyptus oil, 100g Oleum Folium Artemisiae Argyi, 100g Oleum Caryophylli (according to mass ratio 1/3/2/2) mix homogeneously and make " total quintessence oil ".The beta-schardinger dextrin-calcium carbonate microspheres be impregnated in the excessive quintessence oil solution, stir vibrations 48h, microsphere is fully contacted with quintessence oil.After micro-ball load reached capacity, filtering solution took out medicine carrying beta-schardinger dextrin-calcium carbonate microspheres, and oven dry is for subsequent use naturally.
Embodiment 8
Get the dry beta-schardinger dextrin-calcium carbonate microspheres of 100g, get 50g wintergreen oil, 150g eucalyptus oil, 50g Mentholum, 50g thymol (according to mass ratio 1/3/1/1).With the solid material Mentholum and thymol is dissolved in wintergreen oil and eucalyptus oil is prepared into " quintessence oil liquid ".The beta-schardinger dextrin-calcium carbonate microspheres be impregnated in excessive " quintessence oil liquid ", stir vibrations 48h, microsphere surface is fully contacted with quintessence oil.After micro-ball load reached capacity, filtering solution took out medicine carrying beta-schardinger dextrin-calcium carbonate microspheres, and oven dry is for subsequent use naturally.
Embodiment 9
Get the dry beta-schardinger dextrin-calcium carbonate microspheres of 100g, get 50g tea polyphenols, 150g Aloe powder, 50g Mentholum, 50g thymol (according to mass ratio 1/3/1/1) mix homogeneously and make " total quintessence oil ".The beta-schardinger dextrin-calcium carbonate microspheres be impregnated in the excessive quintessence oil solution, stir vibrations 48h, microsphere surface is fully contacted with quintessence oil.After micro-ball load reached capacity, filtering solution took out medicine carrying cyclodextrin calcium carbonate microspheres, and oven dry is for subsequent use naturally.
Medicine carryingβ-
Cyclodextrin calcium carbonate microspheres drug loading is measured
The dry medicine carrying beta-schardinger dextrin-calcium carbonate microspheres of preparation is dissolved in DMSO solution, the microsphere Chinese medicine fully is dissolved in the DMSO solution, and solution is carried out gas chromatography and nuclear magnetic resonance method detection, determine the microsphere drug loading.
Getting the dry medicine carrying beta-schardinger dextrin-calcium carbonate microspheres that 100g is loaded with wintergreen oil, eucalyptus oil, Mentholum, thymol (according to mass ratio 1/3/1/1) is dissolved in the 10ml DMSO solution, stir vibrations 24h, make that carrying medicament fully is dissolved among the solvent in the microsphere.Treat after the solution equilibria, centrifugal filtration solution, and get an amount of solution and carry out chromatography of gases and nuclear magnetic resonance method detection, after analyzing collection of illustrative plates, determine to contain in the medicine " total quintessence oil " amount 22.5g.
Get the dry medicine carrying beta-schardinger dextrin-calcium carbonate microspheres that 100g is loaded with wintergreen oil, eucalyptus oil, Oleum Folium Artemisiae Argyi, Oleum Caryophylli (according to mass ratio 1/3/2/2) and be dissolved in the 10ml DMSO solution, stir vibrations 24h, make that carrying medicament fully is dissolved among the solvent in the microsphere.Treat after the solution equilibria, centrifugal filtration solution, and get an amount of solution and carry out chromatography of gases and nuclear magnetic resonance method detection, after analyzing collection of illustrative plates, determine to contain in the medicine " total quintessence oil " amount 18g.
Medicine carryingβ-
Cyclodextrin calcium carbonate microspheres drug release rate is observed
Get an amount of dry medicine carrying beta-schardinger dextrin-calcium carbonate microspheres, add in the artificial oral-cavity saliva, every certain interval of time goes a small amount of artificial saliva, residual drug content in the test determines salivas such as employing gas chromatogram, and draw medicine release rate profile in time.
Getting the dry medicine carrying beta-schardinger dextrin-calcium carbonate microspheres that 50g is loaded with wintergreen oil, eucalyptus oil, Oleum Folium Artemisiae Argyi, Oleum Caryophylli (according to mass ratio 1/3/2/2) impregnated in the 100ml artificial saliva, every interval 2h saliva that takes a morsel is carried out gas chromatography test, to 24h, stop sampling, draw medicine release profiles in time.Average for parallel three groups.Can find by observing saliva Chinese medicine concentration, after medicine carrying microballoons adds saliva, microsphere has a comparatively rapidly dispose procedure, and saliva Chinese medicine concentration is rapidly increased to 60mg/ml, As time goes on, saliva Chinese medicine concentration rises slowly, extremely final medicine all discharges, and drug level reaches 90mg/ml, and this result shows that this medicine-carried system can reach the progressively effect of slow release, make drug level maintain effect level, as shown in Figure 7.
Preparation take medicine carrying cyclodextrin calcium carbonate microspheres as the oral care product of function raw material
The preparation of embodiment 13 chewing gum
Get the dry medicine carrying beta-schardinger dextrin-of 100g calcium carbonate microspheres, get in 60 ℃ of constant temperature ovens of 500g gum base softening after, fully mix with the sweeting agents such as 30g maltose alcohol, 10g citric acid, 10g phospholipid and emulsifying agent raw material, after raw material is cooled to temperature and is lower than 40 ℃, drop in the noodle cutter and be squeezed into tissue tight, the sugared embryo of ganoid band shape, repeat to push twice, be squeezed to 5cm excision forming when thick, and place about the aging dry 10h of 20 ℃ of conditions, make moisture be controlled at 30% and get final product.
The preparation of embodiment 14 toothpaste
Get the dry medicine carrying beta-schardinger dextrin-of 50g calcium carbonate microspheres, get 450g abrasivus silicon dioxide, the 15g sodium carboxymethyl cellulose, the 25g sodium lauryl sulfate, 50g glycerol, the 5g sweeting agent, the 3g antiseptic, the 2g stabilizing agent, first sweeting agent, antiseptic, glycerol are dissolved in the deionized water, under the vacuum condition aqueous solution are sucked in the cream pot processed, then open blender and add silicon dioxide, sodium carboxymethyl cellulose, sodium lauryl sulfate and medicine carrying granule, treat that mastic mills and stirred 50 minutes, each material mix homogeneously namely makes mastic.Whole process operates under vacuum condition carries out.
Claims (8)
1. the medicine-carried system of a beta-schardinger dextrin-calcium carbonate microspheres is characterized in that, comprises by weight percentage following composition:
Beta-schardinger dextrin-calcium carbonate microspheres 20-95%;
Active constituents of medicine 5-80%.
2. want the medicine-carried system of 1 described beta-schardinger dextrin-calcium carbonate microspheres such as right, it is characterized in that described active component comprises thymol, Mentholum, tea polyphenols, Oleum Caryophylli, wintergreen oil, eucalyptus oil, Oleum Folium Artemisiae Argyi, Oleum Cinnamomi, tea tree ethereal oil, Oleum lavandula angustifolia, Fructus Citri Limoniae oil, litsea cubeba oil, citronella oil, patchouli oil, perilla oil, Fructus Zanthoxyli oil, the Flos Pelargonii quintessence oil, the gin quintessence oil, Radix Oenotherae erythrosepalae quintessence oil, Oleum Vitis viniferae, Herba Origani oil, Flos Rosae Rugosae quintessence oil, Aloe powder, flavone extract, the curcumin extract, anthrone Anthraquinones extract, in organic acid and the alkaloids extract one or more.
3. the preparation method of the medicine-carried system of a beta-schardinger dextrin-calcium carbonate microspheres is characterized in that, comprises following steps:
A) configuration sodium carbonate liquor adds beta-schardinger dextrin-to fully dissolving, obtains the beta-schardinger dextrin-sodium carbonate liquor,
B) it is 4-70 ℃ at stirring condition, mixing speed is under the 300-900rpm, fast the beta-schardinger dextrin-sodium carbonate liquor is joined in the calcium chloride solution with the corresponding molar concentration of sodium carbonate liquor of step in a), in the rear mixing time that feeds intake is controlled at 30 minutes and stirs
C) leave standstill, centrifugal, drying,
D) with step c) the beta-schardinger dextrin-calcium carbonate microspheres of gained adds and contains in the solution of active constituents of medicine, and vibrations are stirred,
E) dry for standby.
4. the preparation method of the medicine-carried system of beta-schardinger dextrin-calcium carbonate microspheres as claimed in claim 3, it is characterized in that, the molar concentration of described sodium carbonate liquor is 50mM-150mM, and the molar concentration of the beta-schardinger dextrin-in the described beta-schardinger dextrin-sodium carbonate liquor is 0.1mM-10mM.
5. the preparation method of the medicine-carried system of beta-schardinger dextrin-calcium carbonate microspheres as claimed in claim 4, it is characterized in that, the molar concentration of described sodium carbonate liquor is 50mM, 100mM or 150mM, and the molar concentration of the beta-schardinger dextrin-in the described beta-schardinger dextrin-sodium carbonate liquor is 0.1mM, 1mM or 10mM.
6. the preparation method of the medicine-carried system of beta-schardinger dextrin-calcium carbonate microspheres as claimed in claim 3 is characterized in that, described stirring condition is 25 or 40 ℃, and mixing speed is 600 or 900rpm, and the rear mixing time that feeds intake was controlled in 10 minutes.
7. an oral care product is characterized in that, contains the medicine-carried system of beta-schardinger dextrin-calcium carbonate microspheres claimed in claim 1.
8. an oral care product is characterized in that, described oral care product is toothpaste or chewing gum.
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| CN103610603A (en) * | 2013-11-22 | 2014-03-05 | 广州市盛龙口腔清洁用品有限公司 | Vinegar-containing toothpaste |
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| CN101400408A (en) * | 2005-08-30 | 2009-04-01 | 吉万奥丹股份有限公司 | Compositions and methods to counteract oral malodour |
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| CN101400408A (en) * | 2005-08-30 | 2009-04-01 | 吉万奥丹股份有限公司 | Compositions and methods to counteract oral malodour |
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| CN103610603A (en) * | 2013-11-22 | 2014-03-05 | 广州市盛龙口腔清洁用品有限公司 | Vinegar-containing toothpaste |
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Application publication date: 20130313 |