CN110314107A - New oral care composition and its preparation method and application - Google Patents

Abstract

The present invention provides a novel oral care composition comprising a lauroyl arginine ethyl ester (LAE) ion pair derivative. The present invention also provides methods of preparing oral care compositions containing the derivatives and oral care compositions prepared therefrom. In the oral care composition of the present invention, its derivatives have the characteristics of natural non-toxicity, efficient bacteriostasis, easy degradation and environmental friendliness.

Description

Novel oral care composition, preparation method and application thereof

technical field

The present invention relates to an oral care composition, in particular to an oral care composition containing a lauroyl arginine ethyl ester derivative (ion pair compound), the lauroyl arginine ethyl ester ion pair has antibacterial effect and can help oral care The composition can maintain the stability of the composition and exert an antibacterial effect while exerting its cleaning, treatment or prevention of dental diseases.

Background technique

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 (eg, arginine-based esters, Sn(II) compounds, cetylpyridinium chloride) have been proposed for oral care, and in particular to combat and be associated with plaque formation of oral infections. 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 formulations.

Due to the near-epidemic incidence of dental erosion, there is a continuing need for how to improve the antimicrobial activity and stability of oral care compositions such as dentifrices.

Ethyl lauroyl arginate (LAE) is an organic compound formed by the condensation of fatty acids and dibasic amino acids. It is a white hygroscopic solid with stable chemical properties in the pH range of 3 to 7 and a melting point of 50 to 58 °C. , 247g of LAE can be dispersed in 1kg of water at this temperature, and its partition coefficient in water and oil is greater than 10, that is, it mainly exists in the water phase. The study found that lauroyl arginine ethyl ester LAE has the characteristics of strong antibacterial ability, low biological toxicity, good metabolism in vivo, and high compatibility with the environment. Among them, the most representative feature is that lauroyl arginine ethyl ester has no residue in metabolism. Relevant studies have shown that lauroyl arginine ethyl ester can be rapidly metabolized naturally in humans and animals, and is first hydrolyzed into lauroyl arginine. (LAS) and ethanol, which is then hydrolyzed to the naturally occurring dietary components lauric acid and arginine, which is further metabolized to carbon dioxide and water, and arginine, which is metabolized to ornithine, urea, and carbon dioxide. All primary metabolites and final products produced during the metabolism of lauroyl arginine ethyl ester are non-toxic and harmless, and are the same as the metabolites in the body of the food ingested by humans and animals daily.

In 2005, the US FDA approved LAE as a GRAS (generally recognized as safe) food additive, and in 2007, it passed the safe food certification of the European Food Safety Authority (EFSA). In China, LAE is licensed to be used as a preservative in more than 20 kinds of food and fresh agricultural products.

Chinese Patent for Invention 200980104596.7, "Protection of Tooth Erosion Using Cationic Surfactant" discloses the application of LAE as a cationic surfactant as a composition for oral use, such as sweets, candies, Tablets, lozenges, lollipops, jellies, jellies, gums, drops or dry powder mixtures of beverage powders intended for dissolution, wherein the LAE compound is 0.001% to 5% by weight, preferably as Concentrations of 0.001% to 2% by weight are present in the composition. In the composition, the presence of LAE produces a microbial effect, provides a source of neutralizing plaque acid, and achieves good results.

Chinese invention patent 201480081262.3, "Mouthwash composition comprising peroxide source and N-acetyl-L-arginine alkyl ester salt" discloses the ratio of LAE and its salt to hydrogen peroxide (H ₂ O ₂ ) Mouthwash, wherein the LAE and its salts are present in the composition at a concentration of 0.05% to 0.4% by weight, preferably 0.1% to 0.3% by weight, capable of having a dual effect of effective whitening activity and antimicrobial activity , and this effect maintains the whitening activity and antimicrobial activity over time.

To sum up, research on LAE has been carried out in the prior art, but there is no relevant report on the use of LAE derivatives for the preparation of oral care products.

SUMMARY OF THE INVENTION

One of the principles of the present invention is that, according to the characteristics of lauroyl arginine ethyl ester LAE with strong antibacterial ability, low biological toxicity, good in vivo metabolism effect, high compatibility with the environment, and no reaction with other compounds at room temperature, further research on LAE was improved to obtain a new derivative, that is, the condensation reaction of LAE with organic acid salts was carried out to obtain LAE ion-pair compounds. As a bacteriostatic agent and preservative component in the preservation of fruits and vegetables, the ion-pair compound has the advantages of better bacteriostatic effect and lower dosage than LAE, thereby being more conducive to the preparation of natural and environmentally friendly fruit and vegetable preservatives.

Therefore, the first object of the present invention is to provide the use of a LAE ion pair compound for preparing an oral care composition, wherein the LAE ion pair compound has a structural formula represented by the following formula (III):

Wherein, the RCOO ^- 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 with antibacterial activity 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. In a preferred embodiment, the organic acid salt is selected from niacin, tartaric acid, oxalic acid.

In any of the above embodiments, the oral care composition is a dentifrice, a tooth cooler, a dental filling or blocker, a gum treatment, and a chewable food product.

In a specific embodiment, the dentifrice is a toothpaste, a tooth powder, a mouthwash, the tooth cooling agent is a chewing gum, a mint, and the gum treatment agent is a drop, a spray, a wipe for treating gum disease, The dental filling or blocking agent is a filling agent or blocking agent for the treatment of dental caries or dental bone marrow of canaliculi and root canals.

In another specific embodiment, the chewable food product is a confection, candy, lozenge, lollipop, jelly, jellies, gummies, and the like.

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

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

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

(2) fully stirring and mixing, and under the condition of heating, reaction generates LAE ionicity compound, and described reaction is shown in following reaction formula:

Wherein, the RCOO ^- 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 with antibacterial activity 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.

(3) after fully reacting, cooling room temperature, vacuum drying after purification, thereby preparing the lauroyl arginine ethyl ester organic acid ion pair compound shown in formula (III);

(4) in the container, the LAE ion-pair compound is dissolved in the organic solvent to obtain the ion-pair compound mother liquor;

(5) At room temperature, get the above-mentioned mother liquor and add it to the matrix of the oral care composition, and stir well to obtain the oral care composition.

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

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

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

In step (3), the vacuum drying conditions are 50°C-100°C; preferably, it is 60°C.

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

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

In another embodiment, the preparation method of the RCOO ^- organic acid salt is as follows: adding the organic acid to a methanol solution, adding an appropriate amount of NaOH, stirring at room temperature until a white solid is precipitated, suction filtration and washing with methanol to obtain organic acid salts.

The fourth object of the present invention is to provide an oral care composition containing the above-mentioned LAE ion-pair compound or prepared by the above-mentioned method, which contains a mass percentage concentration of 0.01-1% or 0.1-1% or 1-2% or 1.5-2% % of LAE ion pair compound; preferably, 0.01-0.1%, 0.05%.

Terms and Definitions:

Ethyl lauroyl arginate (LAE) is an organic compound formed by the condensation of fatty acids and dibasic amino acids. It is a white hygroscopic solid with stable chemical properties in the pH range of 3 to 7 and a melting point of 50 to 58 °C. , 247g of LAE can be dispersed in 1kg of water at this temperature, and its partition coefficient in water and oil is greater than 10, that is, it mainly exists in the water phase. The study found that lauroyl arginine ethyl ester LAE has the characteristics of strong antibacterial ability, low biological toxicity, good metabolism in vivo, and high compatibility with the environment. The most representative feature is that there is no residue in the metabolism of lauroyl arginine ethyl ester. Relevant studies have shown that lauroyl arginine ethyl ester can be rapidly metabolized naturally in humans and animals to generate lauric acid and arginine. Metabolized to ornithine, urea, carbon dioxide and water. All primary metabolites and final products produced during the metabolism of lauroyl arginine ethyl ester are non-toxic and harmless, and are the same as the metabolites in the body of the food that humans and animals ingest daily.

The present invention improves the derivatives of LAE, and breaks through the traditional thinking for the development of derivatives, that is, it is no longer limited to selecting suitable forms of acids, bases, and salts/esters traditionally suitable for LAE, or performing acid, base, The treatment of salt or esterification group, but creative selection of an acid group that can enhance the antibacterial synergistic effect of LAE, and unconventionally combine the two into new derivatives through strong intermolecular ionic bonds, That is, ion-pair compounds, thereby significantly improving the use of LAE derivatives in oral care compositions.

technical effect

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

The invention uses the LAE ion pair compound creatively to replace the bacteriostatic agent and preservative in the oral care composition, while retaining the advantages of low cost, simple production process and good stability of the traditional oral care composition, and also has a significant bacteriostatic effect, It has the advantages of single component, simple preparation, no harm to human body, easy catabolism, easy long-term storage and the like.

Description of drawings

Figure 1: ESI mass spectrum of the cation B+ molecular ion peak of the LAE ion-pair compound;

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

Figure 3: Peak shape and chemical shift diagram of 1H-NMR of LAE;

Figure 4: Peak shape and chemical shift diagram of 1H-NMR of nicotinic acid;

Figure 5: Peak shape and chemical shift diagram of 1H-NMR of LAE nicotinic acid ion pair;

Figure 6: ESI mass spectrum of the anion A-molecular ion peak of the LAE tartrate ion-pair compound.

Detailed ways

In conjunction with the following specific embodiments and accompanying drawings, the present invention will be further described in detail, and the protection content of the present invention is not limited to the following embodiments. Variations and advantages that can occur to those skilled in the art without departing from the spirit and scope of the inventive concept are included in the present invention, and the appended claims are the scope of protection. Processes, conditions, reagents, experimental methods, etc., for implementing the present invention, except for the content specifically mentioned below, are general knowledge and common knowledge in the art, and the present invention has no particular limitation.

Embodiment 1: the preparation method of lauroyl arginine ethyl ester hydrochloride and nicotinic acid synthetic ion pair compound

Dissolve 2.0 g of sodium nicotinate (purchased from Tixiai (Shanghai) Chemical Industry Development Co., Ltd.) in 50 mL of water to prepare a sodium nicotinate salt solution (A); 6.8 g of lauroyl arginine ethyl ester hydrochloride Dissolved in 40 mL of water, heated to 90°C, until all the lauroyl arginine ethyl ester hydrochloride was dissolved to prepare an aqueous solution of lauroyl arginine ethyl ester hydrochloride (B); The saline solution (A) was slowly added to the aqueous lauroyl arginine ethyl ester hydrochloride solution (B), stirred continuously, reacted for 2 hours, cooled to room temperature, filtered, fully washed with purified water, and the precipitate was vacuum-dried at 60°C, That is, 7.6 g of nicotinic acid ion-pair compound was obtained.

Example Analysis of Molecular Formula and Molecular Weight of Compounds with Dilauroyl Arginine Ethyl Ester Nicotinic Acid Ion Pair

The molecular formula of the compound obtained by mass spectrometry, ¹ H-NMR, and ¹³ C-NMR spectral analysis is:

1. Mass Spectrometry (ESI) Analysis

The m/z=385.3 of the cation B ⁺ molecular ion peak, see Figure 1;

Anion A ^- molecular ion peak m/z=122.1, see Figure 2.

The theoretical calculated value of nicotinic acid ion to the cation in the compound is 507.4, and the measured value is in good agreement with the theoretical value.

2. NMR analysis

Lauroyl arginine ethyl ester hydrochloride (see Figure 3), ¹ H-NMR of nicotinic acid (see Figure 4), and ¹ H-NMR of LAE nicotinic acid ion-pair compound (see Figure 5) were compared. Since the LAE ion-pair compound is in the process of salt formation, the peak shape and chemical shift of lauroyl arginine ethyl ester in this ion-pair compound do not change much, but all hydrogens on nicotinic acid have shift changes, and its spectral characteristics are similar to Compared with the original inorganic acid salt (ie LAE hydrochloride), the distance between the two parts of the acid and the base is closer and has an impact. Therefore, it has a corresponding change compared with the original LAE and its hydrochloride. It is not a simple acid-base two. Partial superposition, such as when the precipitate is washed with purified water, has changed the solubility, indicating a strong interaction between all hydrogen nuclei of ethyl lauroyl arginine and niacin through strong ionic bond formation stable single compound structure.

Embodiment three: the preparation method of lauroyl arginine ethyl ester hydrochloride and tartaric acid synthetic ion pair compound

2.0 g of tartaric acid (purchased from Tixiai (Shanghai) Chemical Industry Development Co., Ltd.) was dissolved in 50 mL of methanol, an equivalent of NaOH was added, stirred at room temperature until a white solid was precipitated, suction filtered and washed three times with 30 mL of methanol to obtain sodium tartrate. . Dissolve sodium tartrate in 50 mL of water to prepare an aqueous solution of sodium tartrate (A); dissolve 5.6 g of lauroyl arginine ethyl ester hydrochloride in 40 mL of water, and heat to 90°C until lauroyl arginine ethyl ester salt All the acid salts were dissolved to make lauroyl arginine ethyl ester hydrochloride aqueous solution (B); at 90°C, the sodium tartrate aqueous solution (A) was slowly added to lauroyl arginine ethyl ester hydrochloride aqueous solution ( In B), keep stirring, react for 2 hours, cool to room temperature, filter, fully wash the precipitate with pure water, and dry the precipitate under vacuum at 60°C to obtain 6.3 g of tartaric acid ion pair compound.

Example Four: Analysis of Molecular Weight of Compounds by Lauroyl Arginine Ethyl Ester Tartaric Acid Ion

Mass spectrometry (ESI) analysis of cation B ⁺ molecular ion peak m/z = 385.3 (see Figure 1)

Anion A ^- m/z of molecular ion peak = 149.0 (see Figure 6)

The theoretical calculated value of nicotinic acid ion to the cation in the compound is 534.3, and the measured value is in good agreement with the theoretical value.

Embodiment 5: the preparation method of lauroyl arginine ethyl ester hydrochloride and oxalic acid synthetic ion pair compound

Dissolve 1.0 g of oxalic acid (purchased from Discovery Co., Ltd.) in 50 mL of methanol, add an equivalent of NaOH, stir at room temperature until a white solid is precipitated, filter with suction and wash with 30 mL of methanol for three times to obtain sodium oxalate. Dissolve sodium oxalate in 50 mL of water to prepare a sodium oxalate aqueous solution (A); dissolve 4.7 g of lauroyl arginine ethyl ester hydrochloride in 40 mL of water, and heat to 90°C until lauroyl arginine ethyl ester salt The sodium oxalate solution (A) was slowly added to the lauroyl arginine ethyl ester hydrochloride aqueous solution (B) at 90°C. In B), stirring continuously, reacting for 2 hours, cooling to room temperature, filtering, fully washing the precipitate with pure water, and drying the precipitate under vacuum at 60° C. to obtain 5.0 g of the oxalic acid ion pair compound.

According to the method of Example 2, NMR analysis and ESI analysis were carried out. The results showed that the spectral characteristics of the ion-pair compound were not simply the superposition of two parts of acid and base, and the distance between the two parts of acid and base was close, which had an impact, and its spectral data was the same as the original one. Compared with LAE and its hydrochloride, corresponding changes have occurred. For example, when the precipitate is washed with purified water, the solubility has changed, which indicates that there is a strong interaction between all the hydrogen nuclei of lauroyl arginine ethyl ester and oxalic acid, And formed a stable single compound structure through strong ionic bonds.

Embodiment 6: the preparation method of lauroyl arginine ethyl ester hydrochloride and carbonic acid synthetic ion pair compound

Dissolve 1.0 g of sodium carbonate (purchased from Discovery Co., Ltd.) in 50 mL of water to prepare a sodium carbonate aqueous solution (A); dissolve 4.0 g of lauroyl arginine ethyl ester hydrochloride in 40 mL of water, and heat to 90°C until Lauroyl arginine ethyl ester hydrochloride is completely dissolved to make lauroyl arginine ethyl ester hydrochloride aqueous solution (B); the sodium carbonate aqueous solution (A) is slowly added to lauroyl arginine at 90°C The ethyl ester hydrochloride aqueous solution (B) was continuously stirred, reacted for 2 hours, cooled to room temperature, filtered, fully washed with purified water, and the precipitate was vacuum-dried at 60°C to obtain 4.0 g of carbonate ion pair compound.

According to the method of Example 2, NMR analysis and ESI analysis were carried out. The results showed that the spectral characteristics of the ion-pair compound were not simply the superposition of two parts of acid and base, and the distance between the two parts of acid and base was close, which had an impact, and its spectral data was the same as the original one. Compared with LAE and its hydrochloride, there are corresponding changes, which indicates that all hydrogen nuclei of lauroyl arginine ethyl ester have strong interactions with carbonic acid, and form a stable single compound structure through strong ionic bonds.

Example 7: Determination of minimum inhibitory concentration (MIC) of lauroyl arginine ethyl ester ion-pair compound in vitro

Principle and purpose: According to the micro-broth dilution method stipulated by CLSI, after co-incubating the drug and bacteria in a 96-well plate for 24 hours, the minimum drug concentration that inhibits the growth of bacteria is the minimum inhibitory concentration of the drug.

Method: Lauroyl arginine ethyl ester hydrochloride (LAE hydrochloride) and the organic acid ion pair of lauroyl arginine ethyl ester prepared above were used twice in tryptone soybean broth medium (TSB). Diluted to different concentrations, the drug and bacteria were mixed and incubated in a 96-well plate, and a blank control medium CK1 without bacteria, a medium CK2 supplemented with LAE (1000 μg/ml), and a normal growth control medium CK3 without drugs were set up. . The 96-well plate was incubated in a 37°C incubator for 24 hours, and the absorbance value at 625 nm of each well was measured. Wells with OD ₆₂₅ values consistent with the blank control were considered to have no significant bacterial growth. The lowest concentration of drug without obvious growth of bacteria is the minimum inhibitory concentration MIC (Minimal Inhibitory Concentration) of LAE to bacteria.

The results of the comparison of the antibacterial activities of the prepared various LAE derivatives (ion-pair compounds) with respect to the original LAE compounds are shown in Table 1 below.

Table 1 In vitro antibacterial effects of LAE and its ion-pair compounds against two bacteria

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

Result analysis:

(1) Most of LAE ion-pair compounds maintain the same antibacterial activity against Escherichia coli, especially the antibacterial activity of oxalate ion-pair compounds increases;

(2) Most of the LAE ion-pair compounds maintained the same antibacterial activity against Staphylococcus aureus, the antibacterial activity of the carbonate ion-pair compound decreased, and the antibacterial activity of the niacin ion-pair compound increased significantly;

Conclusion: The ion-pair compounds of LAE derivatives do not inhibit the antibacterial activity of the original LAE of a single component, but are beneficial to the antibacterial activity on the contrary. Among them, the nicotinic acid ion-pair compound produced a significant bacteriostatic effect on Staphylococcus aureus.

Example 8: Suspension Quantitative Method to Test the Effect of Oral Care Products on Killing Oral Bacteria

The mouthwash compositions shown in Table 2 were prepared using conventional methods, except that H ₂ O ₂ was expressed by volume, and the remaining components were expressed by mass percentage (%). Wherein, the control 1-2 is a mouthwash containing cetyl pyridine chloride (CPC) and/or H ₂ O ₂ , and the negative control is blank water.

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

1 ml of the culture was aspirated and centrifuged at 20,000 g for 10 minutes to isolate the bacterial pellet. Then, after the cell pellet was resuspended, 100 μl was dropped in 5 ml of the test solution, and after mixing evenly, 2 min, 5 min, 10 min, and 20 min respectively. Then, take 0.5ml of the mixture and put it in a 5ml PBS test tube, mix well and dilute properly, then take 2-3 dilutions, pipette 0.5ml respectively, put them in two plates, pour them with bacterial agar medium, and then solidify. Invert the plate, incubate at 37°C for 48h, and count the viable colonies.

The experiment was repeated 3 times, and the bacteriostatic rate was calculated:

Bacteriostatic rate=(A-B)×100%/A

Among them, A = the average number of colonies in the control sample

B = the average number of colonies in the test sample

The results are shown in Table 2.

Table 2

Result analysis:

The test results of the antibacterial effect showed that the 0.01% LAE acetate ion pair has achieved a combined antibacterial effect close to that of cetylpyridinium chloride (CPC) and H ₂ O ₂ , but better than that of single use of H ₂ O ₂ . Bacterial effect.

Although in the above experiment, the bacteriostatic effect and detergency of the 0.2% dose group were the highest, and from the patent application submitted by the applicant earlier (invention title: "Lauroyl arginine ethyl ester derivatives and as animals According to the in vitro cell test data of "Use of Antibacterial Agents", Application No.: 201810648982.3), 0.0032% concentration has produced bacteriostatic effect, and increasing the dose of LAE and its derivatives within a certain range can improve the bacteriostatic effect, but Compared with the 0.1% dose group, the bacteriostatic effect was not significantly improved, indicating that the dose range of 0.01%-0.2% has met the production needs

In addition, according to the current relevant national standards (GB15797-2002, Appendix C4), within the prescribed time of application concentration, if the bacteriostatic rate is 50-90%, it has bacteriostatic effect, and >90% has strong bacteriostatic effect. Although increasing the addition amount of LAE and its derivatives will correspondingly increase the bacteriostatic rate, high bacteriostatic rate means more residues, which is not conducive to human health. Even so, since the bacteriostatic components of LAE and its derivatives of the present invention are natural, environmentally friendly and non-toxic components, high-dose addition and use still have the advantage of being friendly and friendly to human body compared with traditional chemical bacteriostatic agents.

Therefore, considering the production cost and actual production needs, the mass percentage concentration of LAE and its ion pair as the active ingredient of the kitchen oil 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%, most preferably 0.05%, which can effectively prevent and control the disease, and 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.