CN114869792A

CN114869792A - Novel oral care compositions, methods of making and uses thereof

Info

Publication number: CN114869792A
Application number: CN202210504145.XA
Authority: CN
Inventors: 易正芳; 邵婷; 仇文卫; 王李婷; 刘明耀
Original assignee: East China Normal University
Current assignee: East China Normal University
Priority date: 2018-06-22
Filing date: 2019-06-21
Publication date: 2022-08-09
Also published as: CN110314107A

Abstract

The present invention provides a novel oral care composition comprising an ethyl Lauroyl Arginine (LAE) ion pair derivative. The invention also provides a method for preparing the oral care composition containing the derivative and the prepared oral care composition. The derivatives of the oral care composition have the characteristics of being natural, non-toxic, efficient and bacteriostatic, easy to degrade and environment-friendly.

Description

Novel oral care compositions, methods of making and uses thereof

The application is a divisional application of Chinese patent application with application date of 2019, 6 and 21, application number of 201910543405.2 and invention name of 'new oral care composition and preparation method and application thereof'.

Technical Field

The invention relates to an oral care composition, in particular to an oral care composition containing lauroyl arginine ethyl ester derivatives (ion pair compounds), wherein the lauroyl arginine ethyl ester ion pair has antibacterial effect, and can help the oral care composition to clean teeth, treat or prevent dental diseases and simultaneously keep the composition stable and exert the antibacterial effect.

Background

Dental plaque is a soft deposit that forms on teeth and includes the accumulation of bacteria and bacterial byproducts. In addition to being unsightly, plaque is also associated with the development of gingivitis and other forms of periodontal disease. Cationic antibacterial agents (e.g., arginine-based esters, sn (ii) compounds, cetylpyridinium chloride) have been proposed for oral care and, in particular, for combating plaque formation and oral infections associated with plaque formation. However, these agents are often incompatible with other ingredients found in dentifrices (i.e., mouthwashes, toothpastes, tooth powders, and chewing gums), thereby reducing their antimicrobial activity in the formulation.

Because of the almost epidemic incidence of dental erosion, there is a continuing need to improve the antimicrobial activity and stability of oral care compositions (e.g., dentifrices).

Lauroyl arginine Ethyl ester (LAE) is an organic matter formed by condensing fatty acid and dibasic amino acid, is a white hygroscopic solid, is chemically stable within the pH range of 3-7, has a melting point of 50-58 ℃, can be dispersed in 1kg of water at the temperature of 247g, has a distribution coefficient of more than 10 in water and oil, and is mainly in a water phase. Researches find that the lauroyl arginine ethyl ester LAE has the characteristics of strong antibacterial capability, low biological toxicity, good in vivo metabolism effect and high environmental compatibility. The most representative characteristic is that no residue is left in the metabolism of lauroyl arginine ethyl ester, and related researches show that lauroyl arginine ethyl ester can be rapidly metabolized naturally in human bodies and animal bodies, is firstly hydrolyzed into Lauroyl Arginine (LAS) and ethanol, then LAS is hydrolyzed into naturally existing dietary components of lauric acid and arginine, the lauric acid is further metabolized into carbon dioxide and water, and the arginine is metabolized into ornithine, urea and carbon dioxide. All primary metabolites and final metabolites produced during the metabolism of lauroyl arginine ethyl ester are non-toxic and harmless, and are the same as the metabolites of food ingested daily by humans and animals in the body.

In 2005, LAE was approved by FDA as a GRAS (generally recognized as safe) food additive in the united states, approved by European Food Safety Administration (EFSA) for safe food certification in 2007, and listed as a standard of food additive general law by 2011 international committee on food code, and is approved as a preservative for 20 kinds of foods and fresh agricultural products.

Chinese patent invention 200980104596.7, "use of cationic surfactants to protect against dental erosion" discloses the administration of LAE as a cationic surfactant as a composition for oral use, such as a dry powder mixture of a confection, a candy, a tablet, a lozenge, a lollipop, a chewy, a jelly, a gum, drops or a powdered drink intended for dissolution, wherein the LAE compound is present in the composition at a concentration of 0.001 to 5% by weight, preferably 0.001 to 2% by weight. In the composition, the presence of LAE produces a microbial effect and provides a source of neutralizing plaque acids, which is highly effective.

Chinese patent 201480081262.3 entitled mouthwash composition containing peroxide source and N-acetyl-L-arginine alkyl ester salt discloses LAE and its salt and hydrogen peroxide (H) ₂ O ₂ ) A proportioned mouthwash wherein the LAE and its salt is present in the composition in a concentration of 0.05 to 0.4% by weight, preferably 0.1 to 0.3% by weight, is capable of having a dual effect of an effective whitening activity and an antimicrobial activity, and the effect is capable of maintaining the whitening activity and the antimicrobial activity over time.

In view of the above, studies on LAE have been conducted in the prior art, but no reports on the use of LAE derivatives for preparing oral care products have been found.

Disclosure of Invention

One principle of the invention is that according to the characteristics that lauroyl arginine ethyl ester LAE has strong antibacterial ability, low biological toxicity, good in vivo metabolism effect, high environmental compatibility and no reaction with other compounds at normal temperature, the LAE is further improved to obtain a novel derivative, namely, LAE and organic acid salt are subjected to condensation reaction, so that the LAE ion pair compound is obtained. The ion pair compound is used as a bacteriostatic agent and a preservative component in the fruit and vegetable fresh-keeping, and has the advantages of better bacteriostatic effect and lower dosage compared with LAE, thereby being more beneficial to preparing natural environment-friendly fruit and vegetable fresh-keeping agent.

Accordingly, it is a first object of the present invention to provide the use of a LAE ion pair compound for the preparation of an oral care composition, wherein the LAE ion pair compound has the formula (III) as shown below:

wherein, the RCOO ^- The organic acid or salt is selected from salicylic acid, formic acid, ammonium formate, calcium formate, acetic acid, sodium diacetate, propionic acid, ammonium propionate, sodium propionate, calcium propionate, butyric acid, sodium butyrate, lactic acid, benzoic acid, sodium benzoate, sorbic acid, sodium sorbate, 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 having antibacterial activity. In a preferred embodiment, the organic acid salt is selected from the group consisting of nicotinic acid, tartaric acid, oxalic acid.

In any of the above embodiments, the oral care composition is a dentifrice, tooth freshener, tooth filler or occluding agent, gum treatment, and food for chewing by the teeth.

In a particular embodiment, the dentifrice is a toothpaste, tooth powder, mouthwash, the tooth freshener is chewing gum, mint, the gum treatment is a drop, spray, wipe for the treatment of gum disease, and the tooth filler or obturating agent is a filler or obturating agent for the treatment of dental caries or tubules, root canals of the bone marrow of a tooth.

In another embodiment, the food chewed by the teeth is a confection, candy, lozenge, lollipop, chewy, jelly, gum, or the like.

In one embodiment, the concentration of the LAE ion pair in the oral care composition is from 0.01 to 2% by mass; preferably, from 0.001 to 0.01%, from 0.01 to 0.1%, from 0.05 to 0.1%, from 0.1 to 0.2%, from 0.01 to 1%, from 0.1 to 1%, from 1 to 2% or from 1.5 to 2%; further preferably, it is 0.05-0.1% or 0.1-0.2%.

It is a third object of the present invention to provide a method of preparing an oral care composition comprising the above LAE ion pair compound, comprising the steps of:

(1) heating and dissolving the compound shown in the formula (II), and then adding an organic acid salt solution;

(2) fully stirring and uniformly mixing, and reacting to generate the LAE ionic compound under the condition of heating, wherein the reaction is shown as the following reaction formula:

wherein, the RCOO ^- The organic acid or salt is selected from salicylic acid, formic acid, ammonium formate, calcium formate, acetic acid, sodium diacetate, propionic acid, ammonium propionate, sodium propionate, calcium propionate, butyric acid, sodium butyrate, lactic acid, benzoic acid, sodium benzoate, sorbic acid, sodium sorbate, 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 having antibacterial activity.

(3) After full reaction, cooling to room temperature, purifying and then drying in vacuum to prepare the lauroyl arginine ethyl ester organic acid ion pair compound shown in the formula (III);

(4) dissolving the LAE ion pair compound in an organic solvent in a container to obtain an ion pair compound mother solution;

(5) adding the mother liquor into the matrix of the oral care composition at room temperature, and stirring thoroughly to obtain the oral care composition.

In the step (1), the heating and dissolving temperature is 50-100 ℃; preferably, it is 90 ℃.

In the step (2), the reaction temperature is 50-100 ℃; preferably, it is 90 ℃.

In the step (2), the reaction time is 50-100 ℃; preferably, it is 90 ℃.

In the step (3), the vacuum drying condition is 50-100 ℃; preferably, it is 60 ℃.

In the step (4), the container is preferably made of stainless steel or inert material.

In the step (4), the organic solvent is methanol, ethanol or the like.

In another embodiment, the RCOO ^- The preparation method of the organic acid salt comprises the following steps: adding the organic acid into a methanol solution, adding a proper amount of NaOH, stirring at room temperature until a white solid is separated out, carrying out suction filtration, and washing with methanol to obtain the organic acid salt.

It is a fourth object of the present invention to provide an oral care composition comprising the above LAE ion pair compound or prepared by the above method, which comprises the LAE ion pair compound in a concentration of 0.01 to 1% by mass, or 0.1 to 1% by mass, or 1 to 2% by mass, or 1.5 to 2% by mass; preferably, it is 0.01-0.1%, 0.05%.

Terms and definitions:

lauroyl arginine Ethyl ester (LAE) is an organic matter formed by condensing fatty acid and dibasic amino acid, is a white hygroscopic solid, is chemically stable within the pH range of 3-7, has a melting point of 50-58 ℃, can be dispersed in 1kg of water at the temperature of 247g, has a distribution coefficient of more than 10 in water and oil, and is mainly in a water phase. Researches find that the lauroyl arginine ethyl ester LAE has the characteristics of strong antibacterial capability, low biological toxicity, good in vivo metabolism effect and high environmental compatibility. The most representative characteristic is that no residue is left in the metabolism of lauroyl arginine ethyl ester, and related researches show that the lauroyl arginine ethyl ester can be rapidly and naturally metabolized in human bodies and animal bodies to generate lauric acid and arginine which are further metabolized into ornithine, urea, carbon dioxide and water. All primary metabolites and final metabolites produced during the metabolism of lauroyl arginine ethyl ester are non-toxic and harmless, and are the same as the metabolites of food ingested daily by humans and animals in the body.

The invention improves the derivatives of the LAE, breaks through the traditional thought of the development of the derivatives, namely, the traditional thought is not limited to selecting the proper forms of acid, alkali and salt/ester which are traditionally suitable for the LAE, or treating the LEA with acid, alkali, salt or esterification groups, but creatively selects an acid radical group which can enhance the bacteriostatic synergistic effect of the LAE and combines the acid radical group and the base radical group into a new derivative, namely an ion pair compound, through strong intermolecular ionic bonds, so that the application of the LAE derivative in oral care compositions is remarkably improved.

Technical effects

The advantages of the oral care composition of the present invention are:

the LAE ion pair compound is creatively used to replace bacteriostatic agents and preservatives in oral care compositions, and the oral care composition has the advantages of low cost, simple preparation process and good stability of the traditional oral care composition, and also has the advantages of obvious bacteriostatic effect, single component, simple preparation, no harm to human bodies, easy catabolism, easy long-term storage and the like.

Drawings

FIG. 1: ESI mass spectrum of cation B + molecular ion peak of LAE ion pair compound;

FIG. 2: ESI mass spectrum of anion A-molecular ion peak of LAE nicotinic acid ion pair compound;

FIG. 3: peak shape and chemical shift pattern of 1H-NMR of LAE;

FIG. 4: peak shape and chemical shift pattern by 1H-NMR of nicotinic acid;

FIG. 5: peak shape and chemical shift pattern by 1H-NMR of LAE nicotinic acid ion pair;

FIG. 6: ESI mass spectrum of LAE tartrate ion on the anion A-molecule ion peak of the compound.

Detailed Description

The present invention will be described in further detail with reference to the following specific examples and drawings, and the present invention is not limited to the following examples. Variations and advantages that may occur to those skilled in the art may be incorporated into the invention without departing from the spirit and scope of the inventive concept, and the scope of the appended claims is intended to be protected. The procedures, conditions, reagents, experimental methods and the like for carrying out the present invention are general knowledge and common general knowledge in the art, except for the contents specifically mentioned below, and the present invention is not particularly limited.

The first embodiment is as follows: preparation method of ion pair compound synthesized from lauroyl arginine ethyl ester hydrochloride and nicotinic acid

Dissolving 2.0g of sodium nicotinate (purchased from Taishiai (Shanghai) chemical industry development Co., Ltd.) in 50mL of water to prepare a sodium nicotinate saline solution (A); dissolving lauroyl arginine ethyl ester hydrochloride 6.8g in 40mL of water, heating to 90 ℃ until the lauroyl arginine ethyl ester hydrochloride is completely dissolved to prepare lauroyl arginine ethyl ester hydrochloride aqueous solution (B); slowly adding the sodium nicotinate aqueous solution (A) into the lauroyl arginine ethyl ester hydrochloride aqueous solution (B) at 90 ℃, continuously stirring, reacting for 2 hours, cooling to room temperature, filtering, fully washing the precipitate with purified water, and performing vacuum drying on the precipitate at 60 ℃ to obtain 7.6g of the nicotinic acid ion pair compound.

Example analysis of molecular formula and molecular weight of compound by dilauroyl arginine ethyl ester nicotinic acid ion pair

By mass spectrometry, ¹ H-NMR、 ¹³ The compound obtained by C-NMR spectroscopy has the formula:

1. mass Spectrometry (ESI) analysis

Cation B ⁺ The molecular ion peak has m/z 385.3, see fig. 1;

anion A ^- The molecular ion peak has m/z of 122.1, see fig. 2.

The theoretical calculation of the niacin ion for the cation in the compound was 507.4, and the observed value coincided with the theoretical value.

NMR analysis

Extracting lauroyl arginine ethyl ester hydrochloride (see FIG. 3), nicotinic acid ¹ H-NMR (see FIG. 4) and of LAE Niacin ion-pair Compounds ¹ H-NMR (see FIG. 5). In the salt forming process of the LAE ion pair compound, the peak shape and chemical shift of lauroyl arginine ethyl ester in the ion pair compound are not changed greatly, but all hydrogen on nicotinic acid has shift change, and the spectral characteristics of the acid and base part are closer to the space distance compared with the original inorganic acid salt (namely LAE hydrochloride), so that the influence is generated, and the corresponding change is generated compared with the original LAE and the hydrochloride thereof, the simple superposition of the acid and base parts is not generated, for example, the solubility is changed when purified water is used for washing and precipitating, which shows that strong interaction is generated between all hydrogen nuclei of the lauroyl arginine ethyl ester and the nicotinic acid, and a stable single compound structure is formed through strong ionic bonds.

Example three: preparation method of ion pair compound synthesized by lauroyl arginine ethyl ester hydrochloride and tartaric acid

2.0g of tartaric acid (purchased from Chiese chemical industry Co., Ltd.) was dissolved in 50mL of methanol, and an equivalent amount of NaOH was added thereto, and the mixture was stirred at room temperature until a white solid was precipitated, and then the solution was filtered under suction and washed with 30mL of methanol three times to obtain a tartaric acid sodium salt. Dissolving sodium tartrate salt in 50mL of water to prepare a sodium tartrate salt aqueous solution (A); dissolving 5.6g of lauroyl arginine ethyl ester hydrochloride in 40mL of water, heating to 90 ℃ until the lauroyl arginine ethyl ester hydrochloride is completely dissolved to prepare lauroyl arginine ethyl ester hydrochloride aqueous solution (B); slowly adding the tartaric acid sodium salt aqueous solution (A) into the lauroyl arginine ethyl ester hydrochloride aqueous solution (B) at 90 ℃, continuously stirring, reacting for 2 hours, cooling to room temperature, filtering, fully washing the precipitate with purified water, and drying the precipitate in vacuum at 60 ℃ to obtain 6.3g of the tartaric acid ion pair compound.

Example analysis of molecular weight of Compounds by Artocylarginine Ethyl ester tartrate ions

Mass Spectrometry (ESI) analysis of cation B ⁺ Molecular ion peak m/z 385.3 (see fig. 1)

Anion A ^- Molecular ion peak m/z 149.0 (see FIG. 6)

The theoretical calculation of the niacin ion for the cation in the compound was 534.3, and the observed value coincided with the theoretical value.

Example five: preparation method for synthesizing ion pair compound by using lauroyl arginine ethyl ester hydrochloride and oxalic acid

Oxalic acid (purchased from research Co., Ltd.) 1.0g was dissolved in 50mL of methanol, and an equivalent amount of NaOH was added thereto, and the mixture was stirred at room temperature until a white solid precipitated, filtered under suction and washed with 30mL of methanol three times to obtain an oxalic acid sodium salt. Dissolving sodium oxalate in 50mL of water to prepare sodium oxalate aqueous solution (A); dissolving 4.7g of lauroyl arginine ethyl ester hydrochloride in 40mL of water, heating to 90 ℃ until the lauroyl arginine ethyl ester hydrochloride is completely dissolved to prepare lauroyl arginine ethyl ester hydrochloride aqueous solution (B); slowly adding the sodium oxalate salt aqueous solution (A) into the lauroyl arginine ethyl ester hydrochloride aqueous solution (B) at 90 ℃, continuously stirring, reacting for 2 hours, cooling to room temperature, filtering, fully washing the precipitate with purified water, and drying the precipitate in vacuum at 60 ℃ to obtain 5.0g of the oxalate ion pair compound.

The results of NMR and ESI analyses performed according to the method of example two show that the ion pair compound is not a simple superposition of two acid and base portions, which are closely spaced and affect the spectral characteristics, and the spectral data of the ion pair compound is changed compared with the original LAE and its hydrochloride, for example, the solubility is changed when the precipitate is washed with purified water, which indicates that all hydrogen nuclei of lauroyl arginine ethyl ester have strong interactions with oxalic acid and form a stable single compound structure through strong ionic bonds.

Example six: preparation method of ion pair compound synthesized by lauroyl arginine ethyl ester hydrochloride and carbonic acid

1.0g of sodium carbonate (purchased from research Co., Ltd.) was dissolved in 50mL of water to prepare an aqueous sodium carbonate solution (A); dissolving 4.0g of lauroyl arginine ethyl ester hydrochloride in 40mL of water, heating to 90 ℃ until the lauroyl arginine ethyl ester hydrochloride is completely dissolved to prepare lauroyl arginine ethyl ester hydrochloride aqueous solution (B); slowly adding the sodium carbonate aqueous solution (A) into the lauroyl arginine ethyl ester hydrochloride aqueous solution (B) at 90 ℃, continuously stirring, reacting for 2 hours, cooling to room temperature, filtering, fully washing the precipitate with purified water, and drying the precipitate in vacuum at 60 ℃ to obtain 4.0g of the carbonate ion pair compound.

The results of NMR and ESI analyses performed according to the method of example two show that the ion pair compound does not have a simple superposition of two acid and base portions, the two acid and base portions are close in space distance and have an influence, and the spectral data of the ion pair compound is changed correspondingly compared with the original LAE and hydrochloride thereof, which indicates that all hydrogen nuclei of the lauroyl arginine ethyl ester have strong interaction with carbonic acid and form a stable single compound structure through strong ionic bonds.

Example seven: determination of lauroyl arginine ethyl ester ion pair compound Minimum Inhibitory Concentration (MIC) in vitro

The principle and the purpose are as follows: according to the microbubult dilution method specified by CLSI, the minimum drug concentration at which bacterial growth is inhibited after 24h of co-incubation of the drug with bacteria in a 96-well plate is the minimum inhibitory concentration of the drug.

The method comprises the following steps: lauroyl arginine ethyl ester hydrochloride (LAE hydrochloride) and the pair of lauroyl arginine ethyl ester organic acid ions prepared above are respectively diluted to different concentrations by Trypticase Soy Broth (TSB), the drug and the bacteria are mixed and incubated in a 96-well plate, and a blank control medium CK1 without bacteria, a medium CK2 added with LAE (1000. mu.g/ml) and a normal growth control medium CK3 without the drug are additionally arranged. The absorbance at 625nm of each well was measured after incubating the 96-well plate in a 37 ℃ incubator for 24 hours. OD with blank control ₆₂₅ Wells with consistent values were considered to have no significant growth of bacteria. The lowest concentration of drug at which bacteria do not significantly grow is the minimum Inhibitory concentration mic (minimum inhibition concentration) of LAE to bacteria.

The results of comparing the antibacterial activity of various LAE derivatives (ion pair compounds) prepared with respect to the original LAE compound are shown in table 1 below.

TABLE 1 in vitro antibacterial Effect of LAE and its ion-pair Compounds on two bacteria

Wherein the percentage value in the bracket () represents the mass percentage of each additive in the reaction system.

And (4) analyzing results:

(1) most of the LAE ion pair compound keeps the same antibacterial activity to escherichia coli, and especially the antibacterial activity of the oxalic acid ion pair compound is increased;

(2) most of LAE ion pair compounds keep the same antibacterial activity to staphylococcus aureus, the antibacterial activity of carbonic acid ion pair compounds is reduced, and the antibacterial activity of nicotinic acid ion pair compounds is obviously improved;

and (4) conclusion: ion pair compounds of LAE derivatives do not inhibit the antibacterial activity of the original LAE in a single component, but are beneficial to the antibacterial activity. Wherein, the nicotinic acid ion pair compound has obvious bacteriostatic effect on staphylococcus aureus.

Example eight: suspension quantitative method for testing oral care product effect of killing oral bacteria

The mouthwash compositions shown in Table 2 were prepared using conventional methods except for H ₂ O ₂ The amounts of the remaining components are expressed in mass percent (%) except in terms of volume. Wherein the control 1-2 contains cetylpyridinium chloride (CPC) and/or H ₂ O ₂ The rinse of (1) and the negative control was blank water.

Streptococcus oralis (ATCC:43146) was inoculated into 50mL of glucose broth and cultured at 37 degrees for 24 h.

1ml of the culture was aspirated and centrifuged at 20000g for 10 minutes to separate the bacterial pellet. Then, resuspending the cell pellet, dropping 100 μ l into 5ml of the test solution, mixing well, and then respectively 2min, 5min, 10min and 20 min. Then, 0.5ml of the mixed solution is placed in a 5MLPBS test tube, mixed evenly and diluted properly, then 2-3 dilutions are taken, 0.5ml of the mixed solution is respectively absorbed and placed in two plates, bacterial agar culture medium is used for pouring, the plates are turned over after solidification, and are cultured for 48h at 37 ℃, and viable colonies are counted.

The test is repeated for 3 times, and the bacteriostasis rate is calculated:

the bacteriostasis rate is (A-B) multiplied by 100%/A

Wherein A is the average colony number of the control sample

B-average colony count of test sample

The results are shown in Table 2.

TABLE 2

And (4) analyzing results:

the results of the bacteriostatic effect tests showed that 0.01% of LAE acetate ion pair had been obtained close to cetylpyridinium chloride (CPC) and H ₂ O ₂ The combined bacteriostasis effect of the (A) is superior to that of the single use of H ₂ O ₂ The bacteriostatic effect of the composition.

Although the bacteriostatic effect and detergency were highest in the 0.2% dose group in the above experiments, and from the in vitro cell test data of the applicant's previously filed patent application (title of the invention: "use of lauroyl arginine ethyl ester derivative as antibacterial agent for animals", application No. 201810648982.3), the bacteriostatic effect was already produced at 0.0032% concentration, and the bacteriostatic effect was improved by increasing the dose of LAE and its derivative within a certain range, but the bacteriostatic effect was not significantly improved with respect to the 0.1% dose group, which indicates that the dose range of 0.01% -0.2% already satisfied the production requirement

In addition, according to the existing national relevant standards (GB15797-2002, appendix C4), in the action time specified by the specified use concentration, if the bacteriostatic rate is 50-90%, the bacteriostatic action is shown, and if the bacteriostatic rate is more than 90%, the bacteriostatic action is stronger. Although increasing the addition of LAE and its derivatives will increase the bacteriostatic rate, too high a bacteriostatic rate means more residue and is not good for human health. Even so, because the bacteriostatic agent components of the LAE and the derivatives thereof belong to natural environment-friendly and nontoxic components, the bacteriostatic agent has the advantage of being friendly to human bodies when being added and used in high dosage compared with the traditional chemical bacteriostatic agent.

Therefore, in consideration of production cost and actual production requirements, the LAE and ions thereof can effectively prevent and treat the diseases when the mass percentage concentration of the LAE and ions thereof to the active ingredients of the kitchen oil stain cleaning agent is 0.01-1%, or 0.1-1%, or 1-2%, or 1.5-2%, preferably the effective concentration is 0.01-0.1%, and most preferably 0.05%, and meet the production requirements.

Claims

Use of a LAE ion pair compound for the preparation of an oral care composition, wherein the LAE ion pair compound is prepared by reacting:

(1) dissolving the compound shown in the formula (II) in water, heating to 90 ℃ until the compound is completely dissolved, and then slowly adding tartrate, carbonate or oxalate solution at 90 ℃;

(2) fully stirring and uniformly mixing, and reacting under the condition of heating to 90 ℃ to obtain an LAE ion pair compound;

(3) after sufficient reaction, the reaction mixture is cooled to room temperature, and is fully washed and purified by purified water and then dried in vacuum, thereby preparing the purified LAE ion pair compound.
2. The use according to claim 1, wherein an oxalate solution is added in step (1).
3. The use of claim 1, wherein the oral care composition is a dentifrice, tooth freshener, tooth filler or occluding agent, gum treatment, and food to be chewed by the teeth.
4. The use according to claim 3,

the dentifrice is toothpaste, dentifrice, or collutory;

the tooth freshener is chewing gum or mint;

the gum therapeutic agent is drop, spray or smearing agent for treating gum diseases;

the dental filling or blocking agent is a filling or blocking agent for treating dental caries or tooth tubules and root canals of tooth marrow;

the food chewed by teeth is sweet food, candy, lozenge, lollipop, chewy, jelly, and gum.
5. The use of claim 1, wherein the LAE ion pair compound is present in the oral care composition at a concentration of 0.001 to 2% by weight.
6. The use of claim 5, wherein the LAE ion pair compound is present in the oral care composition at a concentration of 0.001 to 0.01%, 0.01 to 1%, or 1 to 2% by weight.
7. The use of claim 6, wherein the LAE ion pair compound is present in the oral care composition at a concentration of 0.01 to 0.1%, 0.1 to 1%, or 1.5 to 2% by weight.
8. The use of claim 7, wherein the LAE ion pair compound is present in the oral care composition at a concentration of 0.05 to 0.1% or 0.1 to 0.2% by weight.