CN101495467A - Method for preventing coloration of catechins and dentifrice composition - Google Patents
Method for preventing coloration of catechins and dentifrice composition Download PDFInfo
- Publication number
- CN101495467A CN101495467A CNA2007800277489A CN200780027748A CN101495467A CN 101495467 A CN101495467 A CN 101495467A CN A2007800277489 A CNA2007800277489 A CN A2007800277489A CN 200780027748 A CN200780027748 A CN 200780027748A CN 101495467 A CN101495467 A CN 101495467A
- Authority
- CN
- China
- Prior art keywords
- catechin
- water
- gum
- hydrogel particle
- dentifrice composition
- 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.)
- Granted
Links
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Images
Landscapes
- Pyrane Compounds (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Cosmetics (AREA)
Abstract
The invention is directed to a method for preventing coloration of catechins by adding to catechins, a water-soluble polymer capable of forming a water-insoluble complex with catechins; and hydrogel particles containing a water-insoluble complex of catechins and a polymer capable of forming a water-insoluble complex with catechins. Further, the invention is directed to a dentifrice composition containing hydrogel particles containing catechins and a polymer capable of forming a water-insoluble complex with catechins, a binder and water.
Description
Technical field
The hydrogel particle that the present invention relates to the coloring inhibiting method of catechin and contain the water-insoluble complex compound of catechin.In addition, relate to the dentifrice composition that contains catechin.
Background technology
Contain polyphenols such as catechin and tannic acid in our the known tealeaves.Especially know that catechin has different physiological roles such as the effect, increased blood pressure restraining effect, blood sugar rising restraining effect of antioxygenation, anti-microbial effect, inhibition blood cholesterol concentration.Because catechin itself is the strong anti-oxidation material, therefore oxidation, polymeric problem can appear in preservation.And then the oxidation of catechin and/or polymerization meeting cause variable color, have limited its use range in preparation.Therefore, need to suppress the oxidation and the polymeric method of catechin.
Because the Polyphenols in the product too much can influence the quality of commodity, JP-A 9-47654 is intended to remove Polyphenols, is different from the oxidation and the polymeric method that suppress catechin.
JP-A 8-333380 discloses a kind of tea saponin manufacture method, wherein, with the hot water extraction residue of moisture lower alcohol extraction tealeaves, handles this extracting solution with the water-insoluble polyvinylpyrrolidone, to remove the catechin that exists in this extracting solution.
JP-A 1-218550 discloses a kind of manufacture method of removing the tea liquid of tannic acid, and it comprises: with the tealeaves after the warm water extraction anaerobic treatment, behind the filtration extracting solution, add insoluble polyvinylpyrrolidone and carry out filtering operation.
Known decayed tooth and periodontopathy are to be caused by intraoral bacterium.Therefore, generally adopt and in composition for oral cavity, add sterilant, killing oral cavity bacterium or to suppress its activity, thus prevention decayed tooth and periodontopathy.Particularly advocate naturally in recent years, avoid using the material of chemosynthesis, use natural component as sterilant.For example, known green tea extract and composition tea-polyphenol compound (catechin etc.) thereof can effectively suppress the propagation (for example, JP-A 1-90124, JP-A 2-25413, JP-A 3-86814 etc.) of oral cavity bacterium.According to the record of these documents, green tea extract etc. suppress the propagation of the cause of disease bacterium Porphyromonas gingivalis of the cause of disease bacterium Stereptcoccus mutans of decayed tooth and periodontopathy, and the composition for oral cavity of effective prevention decayed tooth, periodontopathy is provided.But, because polyphenolic substance (catechin etc.) contacts with oxygen oxidation, polymerization promptly take place, thereby significant variable color takes place, therefore, the composition for oral cavity self of cooperation polyphenolic substance through the time variable color be difficult to avoid.As having that the method for the variable color that suppresses it has proposed: for example, in containing the plant milk extract of polyphenol, add carbonatoms 4～5 sugar alcohols (for example Xylitol, erythritol etc.) and enclose method (JP-A2000-297022) in the oxygen impermeable bag more respectively.
On the other hand, method as the effective constituent that cooperates various medicaments, volatility in composition for oral cavity etc. has also proposed following method, promptly, by this composition is encapsulated or in wrap in that shell is medium to make it stable method (JP-A 61-225115, JP-A 1-275520 etc.).
Summary of the invention
The invention provides a kind of coloring inhibiting method of catechin, it adds water-soluble polymers (hereinafter referred to as polymer A) in catechin, and this water-soluble polymers and catechin form the water-insoluble complex compound.
In addition, the invention provides the hydrogel particle that contains the water-insoluble complex compound that forms by catechin and polymer A.
The invention provides the dentifrice composition that contains hydrogel particle, binding agent and water, hydrogel particle contains catechin and water-soluble polymers, and this water-soluble polymers and catechin form the water-insoluble complex compound.
The invention provides the purposes of water-soluble polymers in the painted inhibition of catechin that forms the water-insoluble complex compound with catechin.Further, the invention provides the purposes as toothpaste of the composition that contains hydrogel particle, binding agent and water, wherein, hydrogel particle contains catechin and forms the water-soluble polymers of water-insoluble complex compound with catechin.
Description of drawings
The figure of the relation between the solubility rate of Fig. 1 catechin that to be expression obtain by the test luminance difference that obtains of example 1 with by test example 2.
Fig. 2 is the design sketch of expression dentifrice composition A to gum.
Fig. 3 is the design sketch of expression dentifrice composition B to gum.
Embodiment
Disclose the polyphenol sorbent material that is made of matrix material among the JP-A 9-47654, this matrix material contains insoluble polyvinylpyrrolidone and constitutes in the base material with the regenerated fibre material.
It is catechin etc. that JP-A 8-333380 is intended to remove target compound saponin(e dud in addition, and it is different from oxidation and the polymeric method that suppresses catechin.
JP-A 1-218550 is intended to remove the tannin component in the extracting solution, and it is different from oxidation and the polymeric method that suppresses catechin.
In the prior art, knownly adsorb catechin with polyvinylpyrrolidone, the technology that catechin is removed in absorption, still, the oxidation and/or the polymerization that suppress catechin are not clear with the method that prevents variable color.
The object of the present invention is to provide suppress catechin painted preventing the method for variable color, and the painted hydrogel particle that is inhibited of catechin.
Present inventors find: contain hydrogel particle by making dentifrice composition, comprise catechin in this hydrogel particle and form the particular polymers of water-insoluble complex compound with catechin, can make catechin keep stable, simultaneously can the gel particle be broken easily, thereby catechin is had an effect effectively at the near surface of tooth and gum, and the usability of this dentifrice composition is good.
The invention provides maintenance catechin stablizing in composition, catechin is had an effect effectively to tooth and gum during use, and the good dentifrice composition of usability.
According to the present invention, thereby catechin and polymer A form water-insoluble complex compound stabilization catechin, can suppress the painted of catechin thus.
Toothpaste agent of the present invention can keep the stable of catechin, and catechin is had an effect effectively at the near surface of tooth and gum, can improve the state of tooth and gum, and usability is good.
Among the present invention, catechin is a non-polymerized katechin, for example can enumerate non-phenotype catechins such as catechin, l-Epigallocatechol, catechin and gallate and nutgall catechin gallic acid ester; L-Epicatechol, epigallocatechin, L-Epicatechin gallate and NVP-XAA 723 isophenous catechin etc.Catechin can be by extracting green tea extract with hot water or water-miscible organic solvent from tealeaves, and it is concentrated refining etc. obtaining.In addition, the enriched material of the green tea extracts such as " Sunphenon " of " Polyphenon " by using commercially available Mitsui agricultural (strain) commercial firm, " TEAFURAN " of Yi Tengyuan (strain) commercial firm, sun chemistry (strain) commercial firm, carry out the composition adjustment, and obtain being fit to the green tea extract of the object of the invention.
So long as form the water-soluble polymers of water-insoluble complex compound, then polymer A used among the present invention is not particularly limited with catechin.
In addition, " water-insoluble complex compound " is during with the aqueous solution of the aqueous solution of catechin and polymer A, the insoluble substance of separating out from water.Can be by the turbidity of mixed solution, separating out of water-insoluble complex compound confirmed at the peak of the water-insoluble complex compound that obtains when perhaps measuring mixed solution by laser diffraction/diffuse transmission type particle size distribution device.
As polymer A, can enumerate polyvinylpyrrolidone, polyvinyl alcohol, Natvosol etc., preferably polyethylene pyrrolidone (hereinafter to be referred as PVP).
From the painted viewpoint of effective inhibition catechin, the weight-average molecular weight of polymer A is preferred more than 6000, and is more preferably more than 60000, further preferred more than 400000, most preferably more than 1300000.In addition, from suppressing the viewpoint that the water-insoluble complex compound becomes blocky agglutinator, obtains small water-insoluble complex compound, the weight-average molecular weight of polymer A is preferred below 3000000, more preferably below 2000000.
Among the present invention, the weight-average molecular weight of polymer A is to be the value of light scattering determining by common weight-average molecular weight measuring method.
In the method for the present invention, from the painted viewpoint of effective inhibition catechin, the addition of polymer A is preferably 1～4 times of weight of catechin, more preferably 1～3 times of weight, more preferably 1.2～2.2 times of weight.
Among the present invention, in the aqueous solution of catechin etc., add the aqueous solution of polymer A etc., mix, form the water-insoluble complex compound, thereby can suppress the painted of catechin with mixing machine.
Hydrogel particle of the present invention contains the water-insoluble complex compound that is formed by catechin and polymer A.
Said in this specification sheets " hydrogel " is meant with the moisture swelling body of water as solvent polymer (gel former) that form, that be not dissolved in water.As gel former, preferred natural high moleculer eompound for example can be enumerated Seaweed Extracts such as agar, kappa-carrageenan, ι-carrageenin, lambda-carrageenan, Furcelleran, alginates, propylene glycol alginate; Plant seed viscous substances such as guar gum, Viscogum BE, tamarind seed polysaccharide class, tara gum, cassia gum; Fruit such as pectin, arabogalactan viscous substance; Xanthan gum, Sclerotium gum (Scleroglucan), pulullan polysaccharide, dextran, gelling gum, curdlan production by biological goos such as (Curdlan); Animal proteins such as gelatin, albumin, casein; Plant protein such as soy-protein, aleuronat; Mierocrystalline cellulose and derivatives thereof such as carboxymethyl cellulose, methylcellulose gum, avicel cellulose; Starch and derivatives thereof such as starch, starch-phosphate, starch ethanol acid esters.They can be used singly or two or more kinds mixed.As forming the polymer of the brittle gels particle of easy disintegrating physically, preferred kappa-carrageenan, agar, gelling gum.
In addition, agar is dissolved in the temperature of water generally more than 75 ℃, for its principal constituent at 75～90 ℃.Gelling temperature when agar is dissolved in the water postcooling is 30～45 ℃.
In the hydrogel particle of the present invention, the water-insoluble complex compound of catechin and polymer A is dispersed in the external phase that contains gel former and water, again by they institute's embeddings.Polymer A is with respect to the ratio of the catechin in the water-insoluble complex compound, from the painted viewpoint of effective inhibition catechin, and preferred 1～4 times of weight, more preferably 1～3 times of weight, more preferably 1.2～2.2 times of weight.
From suppressing the viewpoint that the water-insoluble complex compound becomes blocky agglutinator, obtains small water-insoluble complex compound, in the hydrogel particle of the present invention, the content of the water-insoluble complex compound of catechin and polymer A is preferably below the 12 weight %, more preferably below the 8 weight %, further below the preferred 6 weight %.
The destroyed viewpoint of hydrogel particle when preventing during being coupled to other reagent, preferred 0.25～5.0 weight % of the content of the gel former in the hydrogel particle of the present invention, more preferably 0.5～4.0 weight %, further preferred 1.0～3.0 weight %.
Hydrogel particle of the present invention also can contain water-soluble organic compounds such as carbohydrate, polyvalent alcohol except that containing water-insoluble complex compound of the present invention, gel former and water, and composition such as tinting material, sanitas, water soluble flavours.
As carbohydrate, can enumerate glucose, semi-lactosi, fructose, seminose, N.F,USP MANNITOL, sucrose, maltose, lactose etc.
As polyvalent alcohol, can enumerate glycerine, Sorbitol Powder, ethylene glycol, polyoxyethylene glycol, propylene glycol, polypropylene glycol, oligosaccharides etc.
The median size of hydrogel particle of the present invention, from the viewpoint of outward appearance and productivity, preferred 5～10000 μ m, more preferably 100～10000 μ m, further preferred 200～5000 μ m.Adopt the sieve of various mesh numbers, in water, the 100g particle carried out wet classification, remove excessive moisture with filter paper after, gravimetry is represented the median size (sieve method) of hydrogel particle with weight average particle diameter.
In addition, there is no particular limitation to the shape of hydrogel particle of the present invention, preferably has the shape of the rotator that is made of curved surface.At this, so-called " rotator that is made of curved surface " is meant, the Closed Graph that will be made of imaginary axis and continuous curve is that axle is rotated the shape that obtains with the imaginary axis, does not comprise that pyrometric cone and cylinder etc. have the planar shape.The shape of hydrogel particle, from viewpoint attractive in appearance, more preferably spherical or ellipticity.
Manufacturing process to hydrogel particle of the present invention is not particularly limited, for example, agar isogel formation agent, polymer A are mixed with ion exchanged water, be heated to the above temperature of solvent temperature and make it abundant dissolving, after adding the aqueous solution that mixes catechin again, by common drip method, spray method, perhaps paddling process etc. obtains hydrogel particle.
Drip method is to extrude mixed solution from the hole, utilizes the mixed solution be extruded because its surface tension or interfacial tension become the character of drop, with this drop cooling curing in gas phases such as air or in the liquid phase, thus the method for manufacturing hydrogel particle.In addition, from the viewpoint of the hydrogel particle of making uniform particle diameter, the mixed solution that preferred vibration is extruded from the hole.
Spray method is to use spray nozzle, and mixed solution when spray nozzle is sprayed to the gas phase, because its surface tension makes it to form drop, is made this drop cooling curing in gas phase, thereby makes the method for hydrogel particle.
Paddling process; be that blended characteristic and temperature are not adjusted in the liquid more than the gelling temperature in fact with mixed solution having; drop into mixed solution; make the mixed solution micronize by the shearing force that stirs; utilize the character that becomes drop owing to interfacial tension; make this drop with mixed solution cooling curing in the blended liquid in fact not, thereby make the method for hydrogel particle.
In any one method of drip method, spray method and paddling process, when extruding, the temperature of when spraying or the mixed solution when dropping into is preferably more than the gelling temperature and below 100 ℃.In addition, from can making the viewpoint of spherical particle attractive in appearance easily, the temperature of oil type dispersion liquid is preferably more than gelling temperature+10 ℃ in this water, more preferably more than gelling temperature+20 ℃.In addition, the upper limit of this temperature is 100 ℃ of the boiling points of water.
Hydrogel of the present invention can be coupled in makeup, washing composition, the bath agent etc.This external enwergy is used at composition for oral cavity, particularly in the dentifrice composition.
The hydrogel particle that comprises in the dentifrice composition of the present invention contains above-mentioned catechin and forms the water-soluble polymers (hereinafter referred to as polymer A) of water-insoluble complex compound with the plain class of above-mentioned youngster.
In this specification sheets, " hydrogel " is meant with water as the formed moisture swelling body that is not dissolved in the polymer (gel former) of water of solvent.As gel former, preferred natural high moleculer eompound.
The content of catechin in the hydrogel particle of the present invention, from giving full play to the health-care effect of catechin to gum, and from the viewpoint of the stability of hydrogel particle, preferred 0.001～10 quality %, more preferably 0.001～6 quality %, further preferred 0.01～2 quality %.In addition, the content of polymer A from the painted viewpoint of effective inhibition catechin, is preferably 1～4 times of quality of catechin, more preferably 1～3 times of quality, more preferably 1.2～2.2 times of quality.
In addition, the content of the water-insoluble complex compound that comprises in the hydrogel particle, thereby become the viewpoint that block agglutinator obtains small water-insoluble complex compound from suppressing the water-insoluble complex compound, be preferably below the 12 quality %, more preferably below the 8 quality %, more preferably below the 6 quality %.
In the present invention, the gel former that is used for hydrogel particle as mentioned above.
The content of the gel former in the hydrogel particle of the present invention, ruined viewpoint when preventing that hydrogel particle is coupled to dentifrice composition, as mentioned above.
Hydrogel particle of the present invention except that catechin, polymer A, gel former and water, as mentioned above, can also contain compositions such as water-soluble organic compounds such as carbohydrate, polyvalent alcohol, tinting material, sanitas, water soluble flavours.
The manufacture method of hydrogel particle of the present invention as mentioned above.
[dentifrice composition]
Dentifrice composition of the present invention contains above-mentioned hydrogel particle, binding agent and water.
As being used for binding agent of the present invention, can enumerate for example sodium alginate, Xylo-Mucine, carrageenin, xanthan gum, sodium polyacrylate, Natvosol, hydroxypropylcellulose, pectin, tragacanth gum, gum arabic, guar gum, POLY-karaya (karaya gum), Viscogum BE, gelling gum, tamarind seed gum, Semen Plantaginis glue (Psyllium seed gum), polyvinyl alcohol, Sodium chondroitin sulfate A and methoxy EMA anhydride copolymer etc., preferred especially sodium alginate, Xylo-Mucine, carrageenin and xanthan gum.
In the above-mentioned binding agent, preferably 0.5～2.5 product as sodium alginate by the intramolecularly mannuronic acid/guluronic acid of buying easily of sales such as Kimica (strain), DainipponPharma (M/G than).Xylo-Mucine preferably is 0.6～2.5 product, the more preferably product of degree of etherification 0.8～1.5 by the degree of etherification of buying easily of sales such as DAICEL chemistry, the first industrial pharmacy.Carrageenin can use any one in kappa-carrageenan, ι-carrageenin, 3 kinds of isomer of lambda-carrageenan, can use by the commercially available products of buying easily such as Kelco, MRC POLYSACCHARIDE, sun chemistry, more preferably ι-carrageenin, lambda-carrageenan.Xanthan gum can be used by commercially available products of buying easily such as sun chemistry, Kelco, Dainippon Pharma, with carboxymethyl cellulose and time spent, the preferred low xanthan gum of cellulase activity of removing the plain enzyme of small amount of fibers of sneaking in the xanthan gum of using.
Binding agent can use a kind or be used in combination more than 2 kinds, the content of binding agent in the composition is from obtaining storage stability, the viscosity of composition, the viewpoint of stronger refrigerant sense, preferred 0.1～3 quality %, more preferably 0.1～2 quality %, further preferred 0.2～1.2 quality %.
The content of the hydrogel particle in the dentifrice composition of the present invention, from the viewpoint of the stability of dentifrice composition, preferred 0.01～15 quality %, more preferably 0.1～10 quality %, further preferred 1～5 quality %.
The content of the moisture in the dentifrice composition of the present invention is from obtaining the viewpoint of storage stability, stronger refrigerant sense, preferred 1～50 quality %, more preferably 5～40 quality %, further preferred 10～30 quality %.
From the viewpoint of refrigerant sense, ice-cold sense and taste, can further cooperate powder or the granulous erythritol of particle diameter less than 355 μ m in the dentifrice composition of the present invention.There are 3 kinds of isomer such as L-erythritol, D-erythritol, meso-erythritol in the structure of erythritol, can use wherein any one among the present invention.Can use common available product as erythritol, for example can enumerate, recrystallize and crystalloid erythritol of obtaining etc. behind the glucose fermentation.As commercially available product and available crystalloid erythritol has day to grind the product that chemistry (strain), the Foods of Mitsubishi Chemical (strain), Celestare company are made.In addition, the erythritol of big particle diameter re-uses after it can being pulverized and adjusting particle diameter.The pulverizing of erythritol can be used common roller mill, sledge mill, high speed disintegrator, pulverising mill etc., preferably adjusts granularity is easy and production efficiency is high sledge mill, high speed disintegrator.
From in the persistent viewpoint of intraoral coolness, the above and discontented 355 μ m of the preferred 45 μ m of the particle diameter of erythritol, the more preferably above and discontented 300 μ m of 53 μ m, the further above and discontented 250 μ m of preferred 75 μ m.The particle diameter of erythritol when 45 μ m are above, can be in mouth moment dissolve, coolness is lasting thereby preferred.In addition, when the discontented 355 μ m of particle diameter, in mouth, dissolve easily and bring into play coolness.
In addition, the particle diameter of erythritol is measured in mode as described below.
Sieve: JIS standard sieve Φ 75mm
Bore size: from top, be respectively the sieve of 500 μ m, 355 μ m, 250 μ m, 180 μ m, 125 μ m, 90 μ m and 45 μ m bore size, the bottom is a susceptor.
Bobbing machine: Micro type electromagnetic vibration machine M-2 (tube well physics and chemistry is learned apparatus (strain))
Method: the 15g sample is placed on the sieve of 500 μ m, with electromagnetic vibration machine classification 5 minutes.The total amount of the erythritol that will on all sieves of 250 μ m, 180 μ m, 125 μ m, 90 μ m and 45 μ m bore size, stay as particle diameter more than 45 μ m and the erythritol of discontented 355 μ m.
The use level of the erythritol in the dentifrice composition of the present invention, from the viewpoint of refrigerant sense and coolness, preferred 15～60 quality %, more preferably 20～55 quality %, further preferred 25～50 quality %, most preferably 30～50 quality %.
Erythritol preferably is dispersed in the dentifrice composition with powder type.Therefore, preferably in the finishing operation of making, drop into erythritol with powder type.By adopting this method, erythritol almost completely is not dissolved in the water, can exist with powder type in dentifrice composition.
Can also further contain abrasive in the dentifrice composition of the present invention.As abrasive, can enumerate outside the silica products such as precipitation threshold silicon-dioxide, silica gel, aluminosilicate, silconosilicate, gluconosilicate, can also enumerate lime carbonate, secondary calcium phosphate, Calcium Pyrophosphate, aluminium hydroxide, aluminum oxide, magnesiumcarbonate, trimagnesium phosphate etc.Preferred 0～15 quality % of the content of the abrasive in dentifrice composition of the present invention, more preferably 0～12 quality %.
In the dentifrice composition of the present invention, can in not influencing the object of the invention scope, suitably contain other compositions that can be used for composition for oral cavity, for example antioxidant, wetting agent, effective component, whipping agent, sanitas, spices, sweeting agent, pH regulator agent etc.
As antioxidant, the composition that can be used for composition in the oral cavity can be used, for example L-xitix and salt thereof can be enumerated with resistance of oxidation or reducing power, saccharosonic acid and salt thereof, alpha-tocopherol acetate, the dl-alpha-tocopherol, rosemary extract, stevia extract-containing liquid, the sunflower seeds extract, Tenox PG, butylated hydroxytoluene, butylated hydroxy anisole, the L-cysteine salt, phytic acid, Resorcinol and glucosides thereof, nordihydroguaiaretic acid, xitix high-grade aliphatic ester (laurate, stearate, isostearate, cetylate etc.), lignum-vitae resin etc.As the salt of L-xitix, saccharosonic acid or alpha-tocopherol acetic acid, can enumerate the salt of sodium salt, calcium salt, ferrous salt, cetylate etc.These antioxidants can use separately, also can select to use more than 2 kinds.From suppressing the viewpoint that appearance color changes, the content of the antioxidant in the dentifrice composition of the present invention is preferably 0.0005～50 quality %, more preferably 0.001～20 quality %, further preferred 0.01～5 quality %.
Can enumerate for example glycerine, Sorbitol Powder, polyoxyethylene glycol, propylene glycol, ethylene glycol, 1,3 butylene glycol, polypropylene glycol, Xylitol, erythritol, maltose alcohol, Saccharum lactis etc. as wetting agent, can use wherein a kind or be used in combination more than 2 kinds.From guaranteeing the viewpoint of the transparency, the content of these wetting agents in the dentifrice composition of the present invention is preferably 40～95 quality %, more preferably 60～80 quality %.
Dentifrice composition of the present invention can be made dentifrice composition, liquid dentifrice composition, gel dentifrice composition etc. according to well-established law according to purposes.
Embodiment
Set forth enforcement of the present invention below by embodiment.Embodiment is an illustration of the present invention, is not limitation of the invention.
In following examples, the median size of hydrogel particle is measured by above-mentioned sieve method.
Embodiment 1
(ISP makes with the 20g polyvinylpyrrolidone, K-15, weight-average molecular weight 8000) is dissolved in the 330g ion exchanged water and the synthetic aqueous solution (85 ℃), with (sun chemistry (strain) is made with 10g catechin powder, SUNPHENON 100S) is dissolved in the 140g ion exchanged water and the synthetic aqueous solution (20 ℃), mix (8000r/min, 1 minute) with homixerizer, obtain catechin/PVP complex compound aqueous dispersions of forming shown in the table 1.
Table 1
| Weight % | |
| Polyvinylpyrrolidone (K-15) | 4.0 |
| Catechin (SUNPHENON 100S) | 2.0 |
| Ion exchanged water | 94.0 |
(she makes in that foodstuffs industry (strain) with 12.5g agar, UP-37), (ISP makes the PVP of 4g, K-30, weight-average molecular weight 60000), (ISP makes the PVP of 12g, K-90, weight-average molecular weight 1300000) is dissolved in the 321.5g ion exchanged water and the synthetic aqueous solution (85 ℃), the modulation aqueous solution (20 ℃) with 10g catechin powder (SUNPHENON 100S) being dissolved in the 140g ion exchanged water, mix (8000r/min with homixerizer, 1 minute), afterwards, by carrying out the interior bag of the catechin/PVP complex compound hydrogel particle that gas phase is sprayed and obtained composition shown in the table 2.The median size of hydrogel particle is 195 μ m.
Table 2
| Weight % | |
| Agar (UP-37) | 2.5 |
| Polyvinylpyrrolidone (K-30) | 0.8 |
| Polyvinylpyrrolidone (K-90) | 2.4 |
| Catechin (SUNPHENON 100S) | 2.0 |
| Ion exchanged water | 92.3 |
Comparative example 1
10g catechin powder (SUNPHENON 100S) is dissolved in the catechin aqueous solution of modulation 2 weight % in the 490g ion exchanged water.
Test example 1
Bag hydrogel particle in the catechin that use is obtained by embodiment 1/PVP complex compound aqueous dispersions, the catechin/PVP complex compound that obtains by embodiment 2, by the catechin aqueous solution that comparative example 1 obtains, press to form shown in the table 3 and modulate preparation.The preparation that makes was preserved one month down at 50 ℃, measured the luminance difference of preserving front and back according to following method.Estimate the variable color degree according to this luminance difference.The results are shown in table 3.
The assay method of＜luminance difference 〉
In inner capacities the preparation after filling preservation in the transparent vessel (AS ONE society, PS CASENo.1) of 3cm * 3cm * 1cm, sealing.With this container, include camera lens together in, on blank sheet of paper, photograph as 9 points (as depth of shade 1～9) and the CASMATCH (DNP manufacturing) of A, 2,4,6,8,10,12,14, the B of the KODAK GRAY SCALE of depth of shade standard.Photography conditions is under the illumination of annular lamp, to carry out with certain flashing speed, aperture, focal length.Image after the photography is after carrying out colorimetric compensation by the CASMATCH standard on the ADOBE PHOTOSHOP, brightness (Brightness of HSB color model) with the quantitative tested position of WINROOF (three paddy business Co., Ltd.), try to achieve the difference of brightness when preserving 1 month the brightness of goods and beginning for 50 ℃ again by following formula, as the variable color degree.
Variable color degree=(brightness after 50 ℃ are preserved 1 month)-(brightness during beginning)
Table 3
*1: the polyoxyethylene glycol of molecular-weight average 600
*2:CMC＜1150〉Daicel chemistry (strain)
Table 3 shows, when wrapping hydrogel particle in catechin/PVP complex compound of the catechin/PVP complex compound aqueous dispersions that cooperates embodiment 1, embodiment 2, when cooperating the catechin aqueous solution of comparative example 1, variable color has obtained inhibition, particularly when cooperating the hydrogel particle of embodiment 2, variable color has obtained significantly suppressing.Hence one can see that, in catechin/PVP complex compound of catechin/PVP complex compound aqueous dispersions of embodiment 1, embodiment 2 in the bag hydrogel particle, carries out the variable color that oxidation and/or polymerization cause and obtained inhibition owing to catechin, and catechin is stabilized.
Test example 2
Bag hydrogel particle in the catechin that use is obtained by embodiment 1/PVP complex compound aqueous dispersions, the catechin/PVP complex compound that obtains by embodiment 2, by the catechin aqueous solution that comparative example 1 obtains, press to form shown in the table 4 and modulate lauryl sodium sulfate aqueous solution.After at room temperature preserving 1 month, the catechin of stripping is tried to achieve solubility rate in the quantitative as follows lauryl sodium sulfate aqueous solution.The results are shown in table 4.
The quantivative approach of catechin concentration in the＜lauryl sodium sulfate aqueous solution 〉
Get 1.0g sample (lauryl sodium sulfate aqueous solution), mix with 19.0g phosphoric acid buffer and 5.0g tartrate ferron.Measure the absorbancy of modulation back mixed solution at the 540nm place.Then,, draw detection line, thereby calculate the concentration of catechin in the sample, try to achieve solubility rate with the known catechin aqueous solution of catechin powder (SUNPHENON 100S) modulation concentration.In addition, the tartrate ferron is by 100mg ferrous sulfate (7 water salt), 500mg sodium-potassium tartrate being dissolved in water to 100ml and synthetic, phosphoric acid buffer be by with M/15 disodium phosphate soln and M/15 dipotassium hydrogen phosphate solution by 84: 16 mixed and synthetic.
Table 4
The measurement result of the luminance difference of use-testing example 1 will be drawn by the solubility rate of the catechin that obtains of test example 2 and the relation between the luminance difference, the results are shown in Fig. 1.As can be seen from Figure 1, the more little luminance difference of the solubility rate of catechin in lauryl sodium sulfate aqueous solution is just more little.Promptly, when PVP/ catechin complex compound mixes with lauryl sodium sulfate aqueous solution, low discoloration inhibition effect is good more more for the solubility rate of catechin in lauryl sodium sulfate aqueous solution, can suppress the oxidation and/or the polymerization of catechin, the good stability of catechin.
Embodiment 3
PVP (K-30 with 12.5g agar (UP-37), 10.0g, weight-average molecular weight 60000) is dissolved in the 327.5g ion exchanged water and the synthetic aqueous solution (85 ℃), with 5g catechin powder (SUNPHENON 100S) is dissolved in the 145g ion exchanged water and the synthetic aqueous solution (20 ℃), mix (8000r/min with homixerizer, 1 minute), by carrying out the interior bag of the catechin/PVP complex compound hydrogel particle that gas phase is sprayed and obtained composition shown in the table 5 and median size.
As outside the PVP, all the other are identical with embodiment 3 except the PVP (ISP makes, K-60, weight-average molecular weight 400000) that uses 10.0g, obtain forming shown in the table 5 and the interior hydrogel particle that wraps of catechin/PVP complex compound of median size.
Embodiment 5
Except the PVP (K-90, weight-average molecular weight 1300000) that uses 10.0g as outside the PVP, all the other are identical with embodiment 3, obtain forming shown in the table 5 and the interior hydrogel particle that wraps of catechin/PVP complex compound of median size.
Table 5
Test example 3
Bag hydrogel particle in the catechin that use is obtained by embodiment 3～5/PVP complex compound is pressed and is formed the modulation lauryl sodium sulfate aqueous solution shown in the table 6.After at room temperature preserving 10 days, according to the same quantitative lauryl sodium sulfate aqueous solution of method of test example 2 in the catechin of stripping, try to achieve solubility rate.The results are shown in table 6.
Table 6
As can be known from the results of Table 6, the molecular weight of the PVP in the hydrogel particle is high more, and the solubility rate of catechin in lauryl sodium sulfate aqueous solution is just more little.According to the relation of luminance difference of test example 1, as can be known: it is good more that the high more variable color of the molecular weight of PVP suppresses effect, can suppress the oxidation and/or the polymerization of catechin, the good stability of catechin.
The PVP (K-90) of PVP (K-30), the 9.0g of 12.5g agar (UP-37), 3.0g is dissolved in the 325.5g ion exchanged water and the synthetic aqueous solution (85 ℃), with 10g catechin powder (SUNPHENON 100S) is dissolved in the 140g ion exchanged water and the synthetic aqueous solution (20 ℃), mix (8000r/min with homixerizer, 1 minute), afterwards, by carrying out the interior bag of the catechin/PVP complex compound hydrogel particle that gas phase is sprayed and obtained composition shown in the table 7 and median size.
Embodiment 7
The PVP (K-90) of PVP (K-30), the 10.5g of 12.5g agar (UP-37), 3.5g is dissolved in the 323.5g ion exchanged water and the synthetic aqueous solution (85 ℃), the modulation aqueous solution (20 ℃) with 10g catechin powder (SUNPHENON100S) being dissolved in the 140g ion exchanged water, mix (8000r/min with homixerizer, 1 minute), afterwards, by carrying out the interior bag of the catechin/PVP complex compound hydrogel particle that gas phase is sprayed and obtained composition shown in the table 7 and median size.
The PVP (K-90) of PVP (K-30), the 15.0g of 12.5g agar (UP-37), 5.0g is dissolved in the 323.5g ion exchanged water and the synthetic aqueous solution (85 ℃), with 10g catechin powder (SUNPHENON 100S) is dissolved in the 140g ion exchanged water and the synthetic aqueous solution (20 ℃), mix (8000r/min with homixerizer, 1 minute), afterwards, by carrying out the interior bag of the catechin/PVP complex compound hydrogel particle that gas phase is sprayed and obtained composition shown in the table 7 and median size.
Embodiment 9
The PVP (K-90) of PVP (K-30), the 16.5g of 12.5g agar (UP-37), 5.5g is dissolved in the 323.5g ion exchanged water and the synthetic aqueous solution (85 ℃), with 10g catechin powder (SUNPHENON100S) is dissolved in the 140g ion exchanged water and the synthetic aqueous solution (20 ℃), mix (8000r/min with homixerizer, 1 minute), afterwards, by carrying out the interior bag of the catechin/PVP complex compound hydrogel particle that gas phase is sprayed and obtained composition shown in the table 7 and median size.
Table 7
Test example 4
Bag hydrogel particle in the catechin that use is obtained by embodiment 2, embodiment 6～9/PVP complex compound is pressed and is formed the modulation lauryl sodium sulfate aqueous solution shown in the table 8.Preserve under the room temperature after 20 days, according to the same quantitative lauryl sodium sulfate aqueous solution of method of test example 2 in the catechin of stripping, try to achieve solubility rate.The results are shown in table 8.
Table 8
As known from Table 8, when the weight ratio that cooperates catechin/PVP is the hydrogel particle of 1.0/1.6, the solubility rate minimum.That is, when the weight ratio of the catechin/PVP in the hydrogel particle was 1.0/1.6, it is best that variable color suppresses effect, can suppress the painted of catechin, the good stability of catechin.
Continue to set forth dentifrice composition of the present invention with following embodiment.
" % " in the example represents " quality % " when not specifying.
Production Example 1
(she makes in that foodstuffs industry (strain) with 15g agar, UP-37), (ISP makes the PVP of 16g, K-90, weight-average molecular weight 1300000) is dissolved in the 319g ion exchanged water and the synthetic aqueous solution (85 ℃), with with 10g tea extract (SUNPHENON 100S, sun chemistry (strain) is made, catechin content 60～70%) is dissolved in the 140g ion exchanged water and the synthetic aqueous solution (20 ℃), mix (8000r/min with homixerizer, 1 minute) afterwards, obtain the hydrogel particle formed shown in the table 9 by carrying out gas phase spraying.The median size of hydrogel particle is 200 μ m.
Table 9
The composition of hydrogel particle
| The composition title | Ratio (%) |
| Tea extract ( |
2 |
| Agar | 3 |
| PVP | 3.2 |
| Purified Water | Surplus |
| Add up to | 100 |
Hydrogel particle or tea extract (SUNPHENON100S that use is obtained by Production Example 1, sun chemistry (strain) is made, catechin content 60～70%), press modulation dentifrice composition A (reference substance) of composition shown in the table 10 and dentifrice composition B (the present invention's product).To dentifrice composition A and the dentifrice composition B that makes, estimate variable color and taste according to following method.The results are shown in the table 10.In addition, study influence as follows to gum.The results are shown among Fig. 2 and Fig. 3.
The evaluation method of＜variable color 〉
The dentifrice composition that obtains is inserted in the container, preserved one month down, the luminance difference after preserving is measured as follows, estimate its variable color degree according to this luminance difference at 50 ℃.In inner capacities the dentifrice composition after filling preservation in the transparent vessel (AS ONE society, PS CASE No.1) of 3cm * 3cm * 1cm, sealing.With this container, include camera lens together in, on blank sheet of paper, photograph as 9 points (as depth of shade 1～9) and the CASMATCH (DNP manufacturing) of A, 2,4,6,8,10,12,14, the B of the KODAK GRAY SCALE of depth of shade standard.Photography conditions is under the illumination of annular lamp, to carry out with certain flashing speed, aperture, focal length.Image after the photography is after carrying out colorimetric compensation by the CASMATCH standard on the ADOBE PHOTOSHOP, brightness (Brightness of HSB color model) with the quantitative tested position of WINROOF (three paddy business Co., Ltd.), try to achieve the difference of brightness when preserving 1 month the brightness of goods and beginning for 50 ℃ again by following formula (1), with it as the variable color degree.
Variable color degree=(50 ℃ of brightness of preserving down after 1 month)-(brightness during beginning) (1)
The evaluation method of＜taste 〉
By the evaluation group member of 9 specialties, by following 3 grade standards the fragrance of dentifrice composition A and dentifrice composition B is estimated, represent with its mean value.
Judgement criteria
1: do not relate to flavor
2: not too relate to flavor
3: relate to flavor
＜to the influence of gum 〉
Allow 9 more than 20 year old～men and women over fifty years old use dentifrice composition A and dentifrice composition B 1 week separately, before investigation is used and the changing conditions of the BOP (probe is hemorrhage, Bleeding OnProbing) after using.So-called BOP (Bleeding On Probing) is meant the tooth meat bottom of the WHO probe being inserted periodontal pocket (gap of tooth and gum), the hemorrhage state after extracting.If gum health would not do not have hemorrhage, if in periodontal pocket and bottom inflammation is arranged then hemorrhage easily.That is, the value of BOP number positional is many more, and the state of expression gum is bad more.
Table 10
*1: the polyoxyethylene glycol of molecular-weight average 600
*2:SORBSIL AC43 (INEOS Silica manufacturing)
*3:SORBSIL AC15 (INEOS Silica manufacturing)
*4:CMC＜1150〉Daicel chemistry (strain)
*5:SUNPHENON 100S, sun chemistry (strain) is made, catechin content 60～70%
Table 10 shows, contains the dentifrice composition B of the hydrogel particle with packetize in the catechin of the present invention, than the dentifrice composition A that contains the catechin that does not have interior packetize, has significant variable color and suppresses effect, and taste is also good.
In addition, Fig. 2 and Fig. 3 show that when using dentifrice composition A, the value of BOP does not almost change between 1 week, and the state of gum does not improve, still, when using dentifrice composition B, the value step-down of BOP between 1 week, the state of gum is improved.This is considered to because used the catechin of hydrogel particleization, so improved the effect of improving of gingivitis.
Embodiment 11
Hydrogel particle or tea extract (SUNPHENON100S that use is obtained by Production Example 1, sun chemistry (strain) is made, catechin content 60～70%), dentifrice composition C (reference substance) and the dentifrice composition D (product of the present invention) that forms shown in the modulometer 11.Dentifrice composition C that employing method evaluation similarly to Example 10 obtains and variable color and the taste of dentifrice composition D.The results are shown in the table 11.
Table 11
*1～
*5: identical with table 10
*6: erythritol has 5% the size-grade distribution of accounting for that accounts for the above and less than 355 μ m of 82%, 250 μ m that accounts for the above and less than 250 μ m of 13%, 45 μ m of particle diameter less than 45 μ m.
Table 11 shows, contains the dentifrice composition D of the hydrogel particle with packetize in the catechin of the present invention, than the dentifrice composition C that contains the catechin that does not have interior packetize, has significant variable color and suppresses effect, and taste is also good.
Claims (9)
1. the coloring inhibiting method of a catechin is characterized in that,
Add the water-soluble polymers that forms the water-insoluble complex compound with catechin in catechin, this is known as polymer A below water-soluble polymers.
2. inhibition method as claimed in claim 1 is characterized in that,
Described polymer A is a polyvinylpyrrolidone.
3. inhibition method as claimed in claim 1 or 2 is characterized in that,
The weight-average molecular weight of described polymer A is 6000～3000000.
4. as any described inhibition method in the claim 1～3, it is characterized in that,
Interpolation is the polymer A of 1～4 times of weight with respect to catechin.
5. a hydrogel particle is characterized in that,
Contain the water-insoluble complex compound that forms by catechin and the described polymer A of claim 1.
6. hydrogel particle as claimed in claim 5 is characterized in that,
Described polymer A is a polyvinylpyrrolidone.
7. a dentifrice composition is characterized in that,
Contain catechin and contain catechin and the hydrogel particle of the described polymer A of claim 1, binding agent and water.
8. dentifrice composition as claimed in claim 7 is characterized in that,
Described polymer A is a polyvinylpyrrolidone.
9. as claim 7 or 8 described dentifrice compositions, it is characterized in that,
Described binding agent is at least a kind that selects from sodium alginate, Xylo-Mucine, carrageenin, xanthan gum, sodium polyacrylate, Natvosol, hydroxypropylcellulose, pectin, tragacanth gum, gum arabic, guar gum, POLY-karaya, Viscogum BE, gelling gum, tamarind seed gum, Semen Plantaginis glue (Psylliumseed gum), polyvinyl alcohol, Sodium chondroitin sulfate A and methoxy-ethylene copolymer-maleic anhydride.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2006199515A JP4308230B2 (en) | 2006-07-21 | 2006-07-21 | Method for inhibiting catechin coloring |
| JP199515/2006 | 2006-07-21 | ||
| JP2006199516A JP5351379B2 (en) | 2006-07-21 | 2006-07-21 | Toothpaste composition |
| JP199516/2006 | 2006-07-21 | ||
| PCT/JP2007/063202 WO2008010403A1 (en) | 2006-07-21 | 2007-06-26 | Method for preventing coloration of catechins and dentifrice composition |
Publications (2)
| Publication Number | Publication Date |
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| CN101495467A true CN101495467A (en) | 2009-07-29 |
| CN101495467B CN101495467B (en) | 2012-07-25 |
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| CN2007800277489A Expired - Fee Related CN101495467B (en) | 2006-07-21 | 2007-06-26 | Method for preventing coloration of catechins and dentifrice composition |
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| JP (1) | JP4308230B2 (en) |
| CN (1) | CN101495467B (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102665661A (en) * | 2009-12-04 | 2012-09-12 | 花王株式会社 | Hydrogel particles |
| CN103596543A (en) * | 2011-06-17 | 2014-02-19 | 荷兰联合利华有限公司 | An oral care composition |
| CN103622875A (en) * | 2013-12-04 | 2014-03-12 | 中国计量学院 | Preparation method of catechin hydrogel skin care product |
| CN104684412A (en) * | 2012-10-05 | 2015-06-03 | 小川香料株式会社 | Powdery refreshing composition |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5461883B2 (en) * | 2008-08-05 | 2014-04-02 | 三洋電機株式会社 | Non-aqueous electrolyte for secondary battery and non-aqueous electrolyte secondary battery |
| JP2010131479A (en) * | 2008-12-02 | 2010-06-17 | Kao Corp | Hydrogel particle |
| EP2435504B1 (en) | 2009-05-29 | 2020-03-11 | Agency For Science, Technology And Research | Flavonoid hydrogel |
| CN112525844B (en) * | 2020-11-12 | 2024-06-04 | 德莱福(重庆)医疗器械有限公司 | Stable urea concentration test method in dialyser clearance simulation liquid |
-
2006
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102665661A (en) * | 2009-12-04 | 2012-09-12 | 花王株式会社 | Hydrogel particles |
| CN102665661B (en) * | 2009-12-04 | 2014-07-16 | 花王株式会社 | Hydrogel particles |
| CN103596543A (en) * | 2011-06-17 | 2014-02-19 | 荷兰联合利华有限公司 | An oral care composition |
| CN104684412A (en) * | 2012-10-05 | 2015-06-03 | 小川香料株式会社 | Powdery refreshing composition |
| CN103622875A (en) * | 2013-12-04 | 2014-03-12 | 中国计量学院 | Preparation method of catechin hydrogel skin care product |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2008024651A (en) | 2008-02-07 |
| CN101495467B (en) | 2012-07-25 |
| JP4308230B2 (en) | 2009-08-05 |
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