CN110314107A - New oral care composition and its preparation method and application - Google Patents
New oral care composition and its preparation method and application Download PDFInfo
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- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
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Abstract
The present invention provides a kind of new oral care composition comprising lauroyl arginine ethyl ester (LAE) ion pair derivative.The method of oral care composition the present invention also provides preparation containing the derivative and its oral care composition of preparation.Oral care composition of the invention, derivative have the characteristics that Nantural non-toxic, Efficient antibacterial, are easy to degrade, are environmental-friendly.
Description
Technical field
The present invention relates to oral care composition, it is specifically related to containing lauroyl arginine ethyl ester derivative (ion pair
Compound) oral care composition, the lauroyl arginine ethyl ester ion pair have antibacterial effect, oral care can be helped
Composition is while playing it and cleaning the teeth, treats or prevents odontopathy, moreover it is possible to keep composition stable and play antibacterial imitating
Fruit.
Background technique
Plaque is the soft sludge formed on tooth, and the accumulation including bacterium and bacterial by-products.In addition to not
Except refined, bacterial plaque is also related with the generation of gingivitis and the periodontosis of other forms.It has proposed cationic antibacterial agent
(for example, being based on arginic ester, Sn (II) compound, cetylpyridinium chloride) is used for oral care, and especially uses
To resist bacterial plaque formation and form relevant mouth infection to bacterial plaque.However, these reagents usually with dentifrice (i.e. mouthwash,
Toothpaste, tooth powder and chewing gum) in visible other compositions it is incompatible, to reduce its antimicrobial work in the preparation
Property.
Due to the almost epidemic incidence of dental erosion, oral care composition (such as dentifrice) how is improved
Antimicrobial acivity and stability, there is lasting demands.
Lauroyl arginine ethyl ester (Ethyl lauroyl arginate, LAE) is one kind by fatty acid and binary amino
Organic matter made of acid condensation is white hygroscopic solid, and chemical property is stablized in the range of pH3~7,50~58 DEG C of fusing point,
The LAE of 247g is dispersed in the water of 1kg at this temperature, its distribution coefficient in water and in oil is greater than 10, that is, is primarily present in
In water phase.The study found that lauroyl arginine ethyl ester LAE has, strong antibacterial, bio-toxicity is low, internal metabolic effects are good,
The high feature of being compatible with the environment property.And wherein most representative feature is the metabolism noresidue of lauroyl arginine ethyl ester, it is related
Researches show that lauroyl arginine ethyl esters can quickly carry out natural metabolism in human body and animal body, is hydrolyzed into laurel first
Acyl arginine (LAS) and ethyl alcohol, LAS is hydrolyzed to naturally occurring dietary ingredient lauric acid and arginine, lauric acid again later
It can be further metabolized carbon dioxide and water, arginine is then metabolized as ornithine, urea and carbon dioxide.Lauroyl essence
Generated all metabolites and final product are all nontoxic in propylhomoserin ethyl ester metabolic process, with humans and animals
The metabolite of the food of daily ingestion in vivo is identical.
2005, it was GRAS (generally accepted safety) based food additive that U.S. FDA, which ratifies LAE, had passed through Europe within 2007
The safety food of continent food safety management office (EFSA) authenticates, and LAE is included in food additive by Codex Alimentary Commission in 2011
Add in the general code standard of agent, license LAE is as preservative in 20 numerous foods and fresh agricultural products.
Chinese invention patent 200980104596.7, " using cationic surfactant protect tooth erosion " disclose with
LAE is as cationic surfactant as the composition forms application orally used, the oral care group orally used
Closing object is, for example, sweet food, candy, tablet, lozenge, lollipop, toffee, jelly, glycocoll, drops or the drink for being intended for use in dissolution
The powder mixture of feed powder, wherein the LAE compound is with by weight 0.001% to 5%, preferably by weight 0.001%
Concentration to 2% is present in composition.In the composition, due to LAE presence and generate microbial change rules, and provide
The source for neutralizing bacterial plaque acid, obtains good effect.
Chinese invention patent 201480081262.3 " includes peroxide source and N- acetyl-L-arginine alkyl ester salt
Mouthrinse composition " discloses LAE and its salt and hydrogen peroxide (H2O2) proportion mouthwash, wherein the LAE and its salt are to press
The concentration of poidometer 0.05% to 0.4%, preferably by weight 0.1% to 0.3% is present in composition, can have
Effectively whitening and antimicrobial acivity double effects, and the effect can brighten work described in passage maintenance at any time
Property and antimicrobial acivity.
In conclusion having carried out the research to LAE in the prior art, but it yet there are no and LAE derivative is used to prepare mouth
The relevant report of chamber nursing product.
Summary of the invention
One of principle of the invention is, according to lauroyl arginine ethyl ester LAE have strong antibacterial, bio-toxicity it is low,
The characteristics of not reacting under internal metabolic effects are good, being compatible with the environment property is high and room temperature with other compounds, it is further right
LAE is improved, and obtains a kind of new derivatives, i.e., condensation reaction is occurred for LAE and acylate, to obtain LAE ion
To compound.The ion-pair compound has antibacterial as the bacteriostatic agent and preservative ingredient in preserving fruit and vegetable utilizing relative to LAE
Effect is more preferable and the lower advantage of dosage, to be more conducive to prepare the fruit and vegetable fresh-keeping agent of natural environmental-protective type.
Therefore, first goal of the invention of the invention is to provide LAE ion-pair compound and is used to prepare oral care composition
Purposes, wherein the LAE ion-pair compound have the structural formula as shown in following formula (III):
Wherein, the RCOO-Organic acid or salt be selected from salicylic acid with antibacterial activity, formic acid, ammonium formate, calcium formate,
Acetic acid, sodium Diacetate, propionic acid, propionic acid ammonium, sodium propionate, calcium propionate, butyric acid, sodium butyrate, lactic acid, benzoic acid, sodium benzoate, mountain
Pears acid, sodium sorbate, potassium sorbate, fumaric acid, citric acid, potassium citrate, sodium citrate, calcium citrate, tartaric acid, apple
Acid, phosphoric acid, sodium carbonate, oxalic acid or carbonic acid.In a preferred embodiment, the acylate be selected from niacin, tartaric acid,
Oxalic acid.
In any of the above-described embodiment, the oral care composition is dentifrice, tooth freshener, tooth filler
Or blocking agent, gingival therapeutic agent, and the food for passing through teeth chewing.
In a specific embodiment, the dentifrice is toothpaste, tooth powder, mouthwash, and the tooth freshener is mouth
Fragrant sugar, peppermint candy, the gingival therapeutic agent are the drops for treating gum disease, spray, smear agent, the tooth filler or resistance
Suppository is the canaliculi dentales for treating saprodontia or dentale marrow, the filler or blocking agent of canalis radicis dentis.
In another embodiment, the food by teeth chewing be sweet food, candy, lozenge, lollipop,
Toffee, jelly, glycocoll etc..
In one embodiment, mass percent concentration of the LAE ion pair in oral care composition is
0.01-2%；It preferably, is 0.001-0.01%, 0.01-0.1%, 0.05-0.1%, 0.1-0.2%, 0.01-1%, 0.1-
1%, 1-2% or 1.5-2%；It is further preferred that being 0.05-0.1% or 0.1-0.2%.
Third goal of the invention of the present invention is to provide the oral care composition that preparation contains above-mentioned LAE ion-pair compound
Method, step includes:
(1) formula (II) compound represented is dissolved by heating, acylate solution is then added；
(2) mixing is sufficiently stirred, and under heating conditions, reaction generates LAE ion degree compound, and the reaction is such as
Shown in lower reaction equation:
Wherein, the RCOO-Organic acid or salt be selected from salicylic acid with antibacterial activity, formic acid, ammonium formate, calcium formate,
Acetic acid, sodium Diacetate, propionic acid, propionic acid ammonium, sodium propionate, calcium propionate, butyric acid, sodium butyrate, lactic acid, benzoic acid, sodium benzoate, mountain
Pears acid, sodium sorbate, potassium sorbate, fumaric acid, citric acid, potassium citrate, sodium citrate, calcium citrate, tartaric acid, apple
Acid, phosphoric acid, sodium carbonate, oxalic acid or carbonic acid.
(3) sufficiently after reaction, cooling room temperature is dried in vacuo after purification, to prepare the essence of lauroyl shown in formula (III)
Propylhomoserin ethyl ester organic acid ion is to compound；
(4) in a reservoir, LAE ion-pair compound is dissolved in organic solvent, obtains ion-pair compound mother liquor；
(5) at room temperature, it takes above-mentioned mother liquor to be added in the matrix of oral care composition, is sufficiently stirred, to obtain oral cavity
Care composition.
In step (1), the temperature of the heating for dissolving is 50 DEG C -100 DEG C；It preferably, is 90 DEG C.
In step (2), the temperature of the reaction is 50 DEG C -100 DEG C；It preferably, is 90 DEG C.
In step (2), the time of the reaction is 50 DEG C -100 DEG C；It preferably, is 90 DEG C.
In step (3), the vacuum drying condition is 50 DEG C -100 DEG C；It preferably, is 60 DEG C.
In step (4), the container is preferably the container of stainless steel or inertia material.
In step (4), the organic solvent is methanol, ethyl alcohol etc..
In another embodiment, the RCOO-Acylate the preparation method is as follows: by the organic acid be added methanol
In solution, and suitable NaOH is added, is stirred at room temperature until white solid is precipitated, suction filtration is simultaneously washed with methanol point, is obtained organic
Hydrochlorate.
4th purpose of the invention is to provide containing above-mentioned LAE ion-pair compound or by mouth prepared by the above method
Chamber care composition, it includes mass percent concentration be 0.01-1% or 0.1-1% or 1-2% or 1.5-2% LAE from
Son is to compound；It preferably, is 0.01-0.1%, 0.05%.
Term and definition:
Lauroyl arginine ethyl ester (Ethyl lauroyl arginate, LAE) is one kind by fatty acid and binary amino
Organic matter made of acid condensation is white hygroscopic solid, and chemical property is stablized in the range of pH3~7,50~58 DEG C of fusing point,
The LAE of 247g is dispersed in the water of 1kg at this temperature, its distribution coefficient in water and in oil is greater than 10, that is, is primarily present in
In water phase.The study found that lauroyl arginine ethyl ester LAE has, strong antibacterial, bio-toxicity is low, internal metabolic effects are good,
The high feature of being compatible with the environment property.And wherein most representative feature is the metabolism noresidue of lauroyl arginine ethyl ester, it is related
Researches show that lauroyl arginine ethyl esters, and natural metabolism can be quickly carried out in human body and animal body, generates lauric acid and smart ammonia
Acid is further metabolized as ornithine, urea, carbon dioxide and water.Caused by lauroyl arginine ethyl ester metabolic process
All metabolites and final product be all it is nontoxic, with the metabolism of the food of humans and animals daily ingestion in vivo
Product is identical.
The present invention improves the derivative of LAE, breaks through the conventional thought developed for derivative, that is, is no longer limited to
Selection is traditionally suitable for acid, alkali, the salt/ester convenient form of LAE, or the place of acid, alkali, salt or esterified group is carried out to LEA
Reason, but a kind of creative sulfonate groups for selecting antibacterial synergistic effect that can enhance LAE, and unconventionally by the two
It is combined into new derivative, i.e. ion-pair compound by intermolecular strong ionic bond, is spread out to improve LAE significantly
Purposes of the biology in oral care composition.
Technical effect
The advantages of oral care composition of the present invention, is:
Creativeness replaces bacteriostatic agent and preservative in oral care composition using LAE ion-pair compound, is retaining
While the advantage that the low in cost of traditional oral care composition, manufacture craft are simple, stability is good, also there is antibacterial effect
Fruit is significant, and ingredient is single and preparation is simple, to no damage to human body, easily decomposes metabolism, and the advantages that being easy to long-term preservation.
Detailed description of the invention
The ESI mass spectrogram of the cationic B+ molecular ion peak of Fig. 1: LAE ion-pair compound；
The ESI mass spectrogram of the anion A- molecular ion peak of Fig. 2: LAE niacin ion-pair compound；
The peak shape and chemical shift figure of Fig. 3: LAE 1H-NMR；
Fig. 4: the 1H-NMR of niacin peak shape and chemical shift figure；
The peak shape and chemical shift figure of the 1H-NMR of Fig. 5: LAE niacin ion pair；
The ESI mass spectrogram of the anion A- molecular ion peak of Fig. 6: LAE tartaric acid ion-pair compound.
Specific embodiment
In conjunction with following specific embodiments and attached drawing, the present invention is described in further detail, protection content of the invention
It is not limited to following embodiment.Without departing from the spirit and scope of the invention, those skilled in the art it is conceivable that change
Change and advantage is all included in the present invention, and using appended claims as protection scope.Implement mistake of the invention
Journey, condition, reagent, experimental method etc. are in addition to what is specifically mentioned below the universal knowledege of this field and known
Common sense, there are no special restrictions to content by the present invention.
Embodiment one: lauroyl arginine ethyl ester hydrochloride synthesizes the preparation method of ion-pair compound with niacin
Naotin (being purchased from uncommon love (Shanghai) the chemical conversion industry Development Co., Ltd of ladder) 2.0g is dissolved in 50mL water, is prepared
At niacin sodium-salt aqueous solution (A)；Lauroyl arginine ethyl ester hydrochloride 6.8g is dissolved in 40mL water, is heated to 90 DEG C, until
Lauroyl arginine ethyl ester hydrochloride all dissolves, and lauroyl arginine ethyl ester hydrochloride aqueous solution (B) is made；In 90 DEG C of conditions
It is lower that niacin sodium-salt aqueous solution (A) is slowly added into lauroyl arginine ethyl ester hydrochloride aqueous solution (B), it is stirred continuously, instead
It answers 2 hours, is cooled to room temperature, filter, precipitating is sufficiently washed with pure water, precipitate 60 DEG C of vacuum drying to get niacin ion pair
Compound 7.6g.
The analysis of embodiment two lauroyl arginine ethyl ester niacin ion-pair compound molecular formula, molecular weight
By mass spectrum,1H-NMR、13The obtained compound molecule formula of C-NMR Spectrum Analysis are as follows:
1. mass spectrum (ESI) is analyzed
Cationic B+The m/z=385.3 of molecular ion peak, referring to Fig. 1；
Anion A-The m/z=122.1 of molecular ion peak, referring to fig. 2.
Cationic calculated value is 507.4 in niacin ion-pair compound, measured value and theoretical calculation.
2.NMR analysis
By lauroyl arginine ethyl ester hydrochloride (referring to Fig. 3), niacin1H-NMR (referring to fig. 4) and LAE niacin ion
To compound1H-NMR (referring to Fig. 5) compares.Since LAE ion-pair compound is in salification process, in the ion pair
It is little to close the peak shape of lauroyl arginine ethyl ester and chemical shift variation in object, but all hydrogen on niacin have change in displacement,
Compared with former inorganic acid salt (i.e. LAE hydrochloride), soda acid two parts space length is more nearly its Spectral Characteristic, is had an impact,
Therefore it generates corresponding change, is not the two-part superposition of simple soda acid compared with former LAE and its hydrochloride, such as
When pure water washing precipitates, dissolubility has changed, this illustrates between all protons of lauroyl arginine ethyl ester and niacin
Strong interaction is produced, and forms stable single compound structure by strong ionic bond.
Embodiment three: lauroyl arginine ethyl ester hydrochloride synthesizes the preparation method of ion-pair compound with tartaric acid
Tartaric acid (being purchased from uncommon love (Shanghai) the chemical conversion industry Development Co., Ltd of ladder) 2.0g is dissolved in 50mL methanol, is added
The NaOH for entering equivalent is stirred at room temperature until white solid is precipitated, and suction filtration is simultaneously washed with 30mL methanol in three times, obtains tartaric acid
Sodium salt.Sodiotartrate is dissolved in 50mL water, is configured to sodium tartrate saline solution (A)；By lauroyl arginine ethyl ester hydrochloric acid
Salt 5.6g is dissolved in 40mL water, is heated to 90 DEG C, until lauroyl arginine ethyl ester hydrochloride all dissolves, lauroyl is made
Arginine ethyl ester hydrochloride aqueous solution (B)；Sodium tartrate saline solution (A) is slowly added into lauroyl under the conditions of 90 DEG C
It in arginine ethyl ester hydrochloride aqueous solution (B), is stirred continuously, reacts 2 hours, be cooled to room temperature, filter, it is abundant with pure water
Washing precipitating precipitates 60 DEG C of vacuum drying to get tartaric acid ion-pair compound 6.3g.
The analysis of example IV lauroyl arginine ethyl ester tartaric acid ion-pair compound molecular weight
Mass spectrum (ESI) analyzes cation B+The m/z=385.3 of molecular ion peak (referring to Fig. 1)
Anion A-The m/z=149.0 of molecular ion peak (referring to Fig. 6)
Cationic calculated value is 534.3 in niacin ion-pair compound, measured value and theoretical calculation.
Embodiment five: lauroyl arginine ethyl ester hydrochloride synthesizes the preparation method of ion-pair compound with oxalic acid
1.0g (is purchased from and explores Co., Ltd) by oxalic acid to be dissolved in 50mL methanol, the NaOH of equivalent is added, and is stirred at room temperature straight
To white solid is precipitated, filter and is washed in three times with 30mL methanol, oxalic acid sodium salt is obtained.Oxalic acid sodium salt is dissolved in 50mL water,
It is configured to oxalic acid sodium-salt aqueous solution (A)；Lauroyl arginine ethyl ester hydrochloride 4.7g is dissolved in 40mL water, is heated to 90 DEG C,
Until lauroyl arginine ethyl ester hydrochloride all dissolves, lauroyl arginine ethyl ester hydrochloride aqueous solution (B) is made；90
Oxalic acid sodium-salt aqueous solution (A) is slowly added into lauroyl arginine ethyl ester hydrochloride aqueous solution (B) under the conditions of DEG C, constantly
Stirring is reacted 2 hours, is cooled to room temperature, and filters, precipitating is sufficiently washed with pure water, precipitates 60 DEG C of vacuum drying to get grass
Acid ion is to compound 5.0g.
According to the method for embodiment two, NMR analysis and ESI analysis are carried out, the results showed that the wave spectrum of the ion-pair compound
Feature is not the two-part superposition of simple soda acid, and soda acid two parts space length is close, is had an impact, spectral data with
Former LAE and its hydrochloride are compared, and generate corresponding change, such as in pure water washing precipitating, dissolubility has changed, this
Illustrate to produce strong interaction between all protons of lauroyl arginine ethyl ester and oxalic acid, and passes through strong ionic bond
Form stable single compound structure.
Embodiment six: lauroyl arginine ethyl ester hydrochloride synthesizes the preparation method of ion-pair compound with carbonic acid
1.0g (is purchased from and explores Co., Ltd) by sodium carbonate to be dissolved in 50mL water, is configured to aqueous sodium carbonate (A)；It will
Lauroyl arginine ethyl ester hydrochloride 4.0g is dissolved in 40mL water, is heated to 90 DEG C, until lauroyl arginine ethyl ester hydrochloride
All dissolutions, are made lauroyl arginine ethyl ester hydrochloride aqueous solution (B)；It is under the conditions of 90 DEG C that aqueous sodium carbonate (A) is slow
Slowly it is added in lauroyl arginine ethyl ester hydrochloride aqueous solution (B), is stirred continuously, react 2 hours, be cooled to room temperature, mistake
Filter, precipitating is sufficiently washed with pure water, precipitates 60 DEG C of vacuum drying to get carbonate ions to compound 4.0g.
According to the method for embodiment two, NMR analysis and ESI analysis are carried out, the results showed that the wave spectrum of the ion-pair compound
Feature is not the two-part superposition of simple soda acid, and soda acid two parts space length is close, is had an impact, spectral data with
Former LAE and its hydrochloride are compared, and generate corresponding change, this illustrates between all protons of lauroyl arginine ethyl ester and carbonic acid
Strong interaction is produced, and forms stable single compound structure by strong ionic bond.
Embodiment seven: the measurement of the external minimal inhibitory concentration of lauroyl arginine ethyl ester ion-pair compound (MIC)
Principle and purpose: micro broth dilution method, drug and bacterium according to as defined in CLSI are incubated for for 24 hours altogether in 96 orifice plates
Afterwards, the repressed minimum drug concentration of bacterial growth is the minimal inhibitory concentration of the medicine.
Method: by lauroyl arginine ethyl ester hydrochloride (LAE hydrochloride) and above-mentioned prepared lauroyl arginine second
Ester organic acid ion to using (TSB) doubling dilution of trypticase soy broth to exist at various concentration, drug and bacterium respectively
It mixes and is incubated in 96 orifice plates, separately set abacterial blank control culture medium C K1 and add the culture medium of LAE (1000 μ g/ml)
The bacterium normal growth control medium CK3 of CK2 and non-drug containing.96 orifice plates are put into be incubated in 37 DEG C of incubators and are surveyed afterwards for 24 hours
Absorption photometric value at fixed each hole 625nm.With blank control OD625It is worth consistent hole and is considered as bacterium without obvious growth.Bacterium without
The drug minimum concentration obviously grown is minimal inhibitory concentration MIC (Minimal Inhibitory of the LAE to bacterium
Concentration)。
The comparison of antibacterial activity of the prepared a variety of LAE derivatives (ion-pair compound) relative to former LAE compound
As a result as shown in table 1 below.
The in-vitro antibacterial effect of 1 LAE of table and its ion-pair compound to two kinds of bacteriums
Wherein, the percent value in bracket () represents the mass percent of each additive in reaction system.
Interpretation of result:
(1) LAE ion-pair compound is most of keeps identical antibacterial activity, especially oxalic ion to Escherichia coli
The antibacterial activity of compound is risen；
(2) LAE ion-pair compound is most of keeps identical antibacterial activity, carbonate ions to staphylococcus aureus
Antibacterial activity decline to compound, the antibacterial activity of niacin ion-pair compound significantly rise；
Conclusion: the ion-pair compound of LAE derivative will not generate inhibition to the antibacterial activity of the former LAE of single component
Effect, is beneficial to antibacterial activity on the contrary.Wherein, niacin ion-pair compound produces significant suppression to staphylococcus aureus
Bacterium effect.
Embodiment eight: suspension quantitative method tests the effect that oral care product kills oral bacteria
Mouthrinse composition as shown in Table 2 is prepared using conventional method, removes H2O2Indicate outer with volume, remaining group component
It is indicated with mass percent (%).Wherein, control 1-2 is to contain cetylpyridinium chloride (CPC) and/or H2O2Mouthwash,
Negative control is blank water.
Streptococcus oralis (ATCC:43146) is seeded to 50mL dextrose bouillon, 37 degree of cultures are for 24 hours.
1ml culture is drawn, with 20000g centrifugation 10 minutes, separation of bacterial precipitating.Then, by cell precipitation resuspension
Afterwards, take 100 μ l drops in 5ml test fluid, after mixing, respectively at 2min, 5min, 10min, 20min.Then, it takes
0.5ml mixed liquor is placed in 5ML PBS test tube, is mixed and is suitably diluted, then takes 2-3 dilution, draw 0.5ml respectively,
Two plates are placed in, is poured into bacteria Agr culture medium, plate is overturn after solidification, with 37 degree of culture 48h, bacterium colony meter of laboring
Number.
Test is repeated 3 times, and calculates bacteriostasis rate:
Bacteriostasis rate=(A-B) × 100%/A
Wherein, A=control sample average colony number
B=test sample average colony number
The results are shown in Table 2.
Table 2
Interpretation of result:
Fungistatic effect testing result shows, 0.01% LAE acetato- is to having been achieved with close to hexadecyl
Pyridine (CPC) and H2O2Combination effect, but be better than single use H2O2Fungistatic effect.
Although in above-mentioned experiment, the fungistatic effect and detergency of 0.2% dosage group are highests, and first from applicant
(denomination of invention: " lauroyl arginine ethyl ester derivative and the use as animal antibacterial agent from the point of view of the patent application of submission
On the way ", application number: 201810648982.3) from the point of view of cell assay in vitro data, 0.0032% concentration has generated antibacterial effect
Fruit, and fungistatic effect can be improved in LAE and its a certain range of dosage increasing of derivative, but relative to 0.1% dosage group
Fungistatic effect does not increase significantly, illustrates that the dosage range of 0.01%-0.2% has met production needs
In addition, being made in regulation using concentration guidelines according to existing relevant national standard (GB15797-2002, appendix C 4)
With in the time, if bacteriostasis rate is to have bacteriostasis in 50-90%, > 90% is stronger bacteriostasis.Although improve LAE and its
The additive amount of derivative can correspondingly increase bacteriostasis rate, but excessively high bacteriostasis rate means more residual, is not conducive to human body
Health.Even so, the bacteriostatic agent due to LAE and its derivative of the invention is at belonging to the nontoxic ingredient of natural environmental-protective, because
The addition of this high dose has the advantages that using still than traditional chemicals bacteriostatic agent friendly to human body affine.
Accordingly, it is considered to arrive production cost and needs of production, therefore LAE and its ion pair are cleaned as kitchen greasy dirt
The mass percent concentration of the active constituent of agent is 0.01-1% or 0.1-1% or 1-2% or 1.5-2%, preferably effective concentration
For 0.01-0.1%, most preferably 0.05% when can effectively prevent morbidity, meet the needs of production.
Claims (10)
1.LAE ion-pair compound is used to prepare the purposes of oral care composition, which is characterized in that the LAE ion pair
Closing object has the structural formula as shown in following formula (III):
Wherein, the RCOO-Organic acid or salt be selected from salicylic acid with antibacterial activity, formic acid, ammonium formate, calcium formate, acetic acid,
Sodium Diacetate, propionic acid, propionic acid ammonium, sodium propionate, calcium propionate, butyric acid, sodium butyrate, lactic acid, benzoic acid, sodium benzoate, sorbic acid, mountain
Pears acid sodium, potassium sorbate, fumaric acid, citric acid, potassium citrate, sodium citrate, calcium citrate, tartaric acid, malic acid, phosphoric acid,
Sodium carbonate, oxalic acid or carbonic acid.
2. purposes as described in claim 1, which is characterized in that the acylate is selected from niacin, tartaric acid, oxalic acid.
3. purposes as described in claim 1, which is characterized in that the oral care composition be dentifrice, tooth freshener,
Tooth filler or blocking agent, gingival therapeutic agent, and the food for passing through teeth chewing.
4. purposes as claimed in claim 3, which is characterized in that
The dentifrice is toothpaste, tooth powder, mouthwash；
The tooth freshener is chewing gum, peppermint candy；
The gingival therapeutic agent is the drops for treating gum disease, spray, smears agent；
The tooth filler or blocking agent are the canaliculi dentales for treating saprodontia or dentale marrow, the filler or blocking agent of canalis radicis dentis；
The food by teeth chewing is sweet food, candy, lozenge, lollipop, toffee, jelly, glycocoll.
5. purposes as described in claim 1, which is characterized in that the LAE ion-pair compound is in oral care composition
Mass percent concentration be 0.01-2%.
6. purposes as claimed in claim 5, which is characterized in that the LAE ion-pair compound is in oral care composition
Mass percent concentration be 0.001-0.01%, 0.01-0.1%, 0.05-0.1%, 0.1-0.2%, 0.01-1%, 0.1-
1%, 1-2% or 1.5-2%.
7. a kind of preparation method of oral care composition, which comprises the following steps:
(1) formula (II) compound represented is dissolved by heating, acylate solution is then added；
(2) mixing is sufficiently stirred, and under heating conditions, reaction generates LAE ion degree compound, the following reaction of reaction
Shown in formula:
Wherein, the RCOO-Organic acid or salt be selected from salicylic acid with antibacterial activity, formic acid, ammonium formate, calcium formate, acetic acid,
Sodium Diacetate, propionic acid, propionic acid ammonium, sodium propionate, calcium propionate, butyric acid, sodium butyrate, lactic acid, benzoic acid, sodium benzoate, sorbic acid, mountain
Pears acid sodium, potassium sorbate, fumaric acid, citric acid, potassium citrate, sodium citrate, calcium citrate, tartaric acid, malic acid, phosphoric acid,
Sodium carbonate, oxalic acid or carbonic acid；
(3) sufficiently after reaction, cooling room temperature is dried in vacuo, after purification to prepare LAE shown in formula (III) to compound；
(4) in a reservoir, above-mentioned LAE ion-pair compound is dissolved in organic solvent, obtains LAE ion-pair compound mother liquor；
(5) at room temperature, it takes the LAE ion-pair compound mother liquor to be added in the matrix of oral care composition, is sufficiently stirred, from
And obtain oral care composition.
8. the method for claim 7, which is characterized in that in step (1), the temperature of the heating for dissolving is 50 DEG C -100
℃；In step (2), the temperature of the reaction is 50 DEG C -100 DEG C.
9. containing LAE ion-pair compound described in claim 1 or the mouth being prepared by claim 7-8 the method
Chamber care composition, which is characterized in that it includes mass percent concentration be 0.01-1% or 0.1-1% or 1-2% or 1.5-
2% LAE ion-pair compound.
10. oral care composition as claimed in claim 9, which is characterized in that it includes mass percent concentration be 0.01-
0.1%, 0.05% LAE ion-pair compound.
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| CN101227884A (en) * | 2005-08-01 | 2008-07-23 | 米雷特实验室股份公司 | Corrosion protection system including cationic surfactant |
| CN101500552A (en) * | 2006-08-03 | 2009-08-05 | 米雷特实验室股份公司 | Antiviral use of cationic surfactant |
| US20090318557A1 (en) * | 2003-12-22 | 2009-12-24 | Stockel Richard F | Dermatological compositions |
| CN106565546A (en) * | 2016-10-21 | 2017-04-19 | 武汉桀升生物科技有限公司 | Lauroyl arginine ethyl ester glycol acid salt and preparation method and application thereof |
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| AR070271A1 (en) * | 2008-02-13 | 2010-03-25 | Miret Lab | USE OF CATIONIC TENSIOACTIVES FOR PROTECTION AGAINST DENTAL EROSION AND COMPOSITION FOR ORAL USE |
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2019
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|---|---|---|---|---|
| US20090318557A1 (en) * | 2003-12-22 | 2009-12-24 | Stockel Richard F | Dermatological compositions |
| CN101227884A (en) * | 2005-08-01 | 2008-07-23 | 米雷特实验室股份公司 | Corrosion protection system including cationic surfactant |
| CN101500552A (en) * | 2006-08-03 | 2009-08-05 | 米雷特实验室股份公司 | Antiviral use of cationic surfactant |
| CN106565546A (en) * | 2016-10-21 | 2017-04-19 | 武汉桀升生物科技有限公司 | Lauroyl arginine ethyl ester glycol acid salt and preparation method and application thereof |
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