CN110403846A

CN110403846A - New cosmetic composition and its preparation method and application

Info

Publication number: CN110403846A
Application number: CN201910548558.6A
Authority: CN
Inventors: 易正芳; 邵婷; 仇文卫; 刘明耀
Original assignee: East China Normal University
Current assignee: East China Normal University
Priority date: 2018-06-22
Filing date: 2019-06-24
Publication date: 2019-11-05
Also published as: CN115089504A

Abstract

The present invention provides a kind of preservative for cosmetics comprising lauroyl arginine ethyl ester (LAE) ion pair derivative.The method of cosmetics the present invention also provides preparation containing the preservative and its cosmetic composition of preparation.Cosmetic composition of the invention, preservative have the characteristics that Nantural non-toxic, Efficient antibacterial, are easy to degrade, are environmental-friendly.

Description

New cosmetic composition and its preparation method and application

Technical field

The present invention relates to cosmetic composition, it is specifically related to containing lauroyl arginine ethyl ester derivative (ion pair Close object) cosmetic composition, the lauroyl arginine ethyl ester ion pair have antibacterial effect, cosmetic composition can be helped to exist While playing make-up and beauty function, moreover it is possible to keep composition stable and play antibacterial effect.

Background technique

Cosmetics refer to any position that human body surface is interspersed among with smearing, sprinkling or other similar method, such as skin Skin, hair refer to toenail, lips and teeth etc., to reach cleaning, maintenance, beauty, modification and change appearance, or amendment human scent, it protects Hold the chemical industrial product or fine chemical product for the purpose of kilter.

Since cosmetics are included there are many organic matter nutritional ingredient, in order not to allow these nutritional ingredients to generate bacterium, cause Skin care products is rotten, and preservative is added in cosmetics, inhibits the growth and breeding of bacterium, fungi, avoids cosmetics from generating rotten Phenomenon, to maintain freshness and lasting effect.

The type of preservative is extensive, primary differentiation preservative and natural antiseptic agent, and effect specifically includes that

(1) growth and breeding for inhibiting microorganism keep the property of cosmetics to stablize, and make not variable after its use of uncapping Matter extends the holding time；

(2) demand of the more cosmetics of moisture to preservative is larger, such as toner, lotion；And closer to ointment or The cosmetics of wax, microorganism are more difficult to survive, and the demand to preservative is relatively small.

(3) it is compounded in Cosmetic Manufacture usually using several preservatives, expands antibacterial range to reach, improves medicine Effect, anti-secondary pollution and other effects.Common preservative includes benzoic acid, sodium benzoate, Phenoxyethanol, the different thiophene of methyl in cosmetics Oxazoline ketone (abbreviation MIT), salicylic acid, sorbic acid, para hydroxybenzene potassium acid esters, resorcinol, boric acid.With the development of society, developing Nantural non-toxic type preservative becomes research hotspot in the various fields including cosmetics, food.

Although suitable preservative is nontoxic to the human body, even if being that micro constitutent long-time service can also affect people. For example, Phenoxyethanol, is preservative common in cosmetics, the concentration in cosmetics is generally 0.5% to 1%.Benzene oxygen second Alcohol be under intermediate concentration it is toxic, brain and nervous system can be had an impact.For another example, hydroxybenzoic acid esters preservative exists The highest limitation of single ester is 0.4% in cosmetics, mixed ester 0.8%.Once it has been reported that being excessively used in cosmetics to hydroxyl Yl benzoic acid ester can cause contact dermatitis.

Other mould inhibitors for being commonly used for cosmetics are as follows:

It can be seen that currently used preservative, additive amount is all higher, how to guarantee the effect of bacteria mildew-proof In the case of, while minimum additive amount (be, for example, less than 0.05%, be even less than 0.01%) is kept, it is anti-for cosmetics to become research and development The research hotspot of rotten agent.

Lauroyl arginine ethyl ester (Ethyl lauroylarginate, LAE) is one kind by fatty acid and binary amino acid Organic matter made of condensation, be white hygroscopic solid, in the range of pH3~7 chemical property stablize, fusing point 50~58, DEG C should At a temperature of the LAE of 247g be dispersed in the water of 1kg, its distribution coefficient in water and in oil is greater than 10, that is, is primarily present in water Xiang Zhong.The study found that lauroyl arginine ethyl ester LAE have strong antibacterial, bio-toxicity is low, internal metabolic effects are good, with The high feature of Environmental compatibility.And wherein most representative feature is the metabolism noresidue of lauroyl arginine ethyl ester, correlation is ground Natural metabolism can quickly be carried out in human body and animal body by studying carefully display lauroyl arginine ethyl ester, generate lauric acid and arginine, Further it is metabolized as ornithine, urea, carbon dioxide and water.It is generated all in lauroyl arginine ethyl ester metabolic process Metabolite and final product be all it is nontoxic, with the metabolite phase of the food of humans and animals daily ingestion in vivo Together.

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 cosmetic combinations orally used Object is, for example, sweet food, candy, tablet, lozenge, lollipop, toffee, jelly, glycocoll, drops or the beverage for being intended for use in dissolution The powder mixture of powder, wherein the LAE compound is arrived with by weight 0.001% to 5%, preferably by weight 0.001% 2% concentration is present in composition.In the composition, due to LAE presence and generate microbial change rules, and provide neutralization The source of 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 by weight The concentration of meter 0.05% to 0.4%, preferably by weight 0.1% to 0.3% is present in composition, can have effectively The double effects of whitening and antimicrobial acivity, and the effect can passage at any time remain described whitening and anti- Microbial activity.

Chinese patent application CN201280027864, entitled " the makeup sun-screening agent with improved water resistance Or dermatology's sun-screening agent " purposes that a kind of LAE is used to prepare makeup sun-screening agent or dermatology's sun-screening agent, said preparation are disclosed It further include -10 stearate of emulsifier polyglycerol other than UV lightscreening agent.

In conclusion having carried out the research to LAE in the prior art, but yet there are no LAE, even LAE derivative Relevant report for cosmetics anticorrosive mildewproof.Meanwhile although LAE and its conventional derivatives are with a wide range of applications, Its core patent rests in the developed countries such as America and Europe, for fields such as the health cares of being served China as early as possible, and The needs in " planning of 2025 strategic development of made in China " about biological medicine and its related application are responded, are badly in need of research now The new application and new derivatives of LAE and application, to realize that China's biotechnology overtakes other vehicles to the bend of American-European countries, to take It is engaged in the great target of science and technology power.

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, further to LAE It improves, obtains a kind of new derivatives, i.e., condensation reaction is occurred into for LAE and acylate, to obtain LAE ion pair Close object.The ion-pair compound has fungistatic effect more as the bacteriostatic agent and preservative ingredient in cosmetics, relative to LAE The good and lower advantage of dosage, to be more conducive to prepare the cosmetics preservative 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 cosmetic composition Purposes, wherein the LAE ion-pair compound 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, sorb 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 acylate is selected from niacin, tartaric acid, oxalic acid.

In any of the above-described embodiment, the cosmetic composition is face cream, toner, clarifying lotion, make up remover, makeup Lotion, facial mask, lipstick, mousse, nail polish etc..

Wherein, mass percent concentration of the LAE ion-pair compound in cosmetic composition is 0.0030-1%； It preferably, is 0.0030-0.01,0.01-1%；It is further preferred that being 0.0032-0.01%, 0.01-0.05%, 0.05- 0.1%.

Third goal of the invention of the present invention is to provide cosmetic composition of the preparation containing above-mentioned LAE ion-pair compound Method, step include:

(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 as follows Shown in reaction equation:

(3) sufficiently after reaction, cooling room temperature is dried in vacuo, after purification to prepare lauroyl essence ammonia shown in formula (III) Acetoacetic 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 cosmetic composition, is sufficiently stirred, to obtain cosmetics 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 one embodiment, wherein the RCOO^-Organic acid or salt are selected from the salicylic acid with antibacterial activity, first Acid, ammonium formate, calcium formate, acetic acid, sodium Diacetate, propionic acid, propionic acid ammonium, sodium propionate, calcium propionate, butyric acid, sodium butyrate, lactic acid, benzene Formic acid, sodium benzoate, sorbic acid, sodium sorbate, potassium sorbate, fumaric acid, citric acid, potassium citrate, sodium citrate, citric acid Calcium, tartaric acid, malic acid, phosphoric acid, sodium carbonate, oxalic acid or carbonic acid.In a preferred embodiment, the organic acid is selected from cigarette Acid, tartaric acid, oxalic acid.

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 change prepared by the above method Cosmetic compositions.

In any of the above-described embodiment, wherein mass percent of the LAE ion-pair compound in cosmetic composition Concentration is 0.0030-0.01,0.01-1%.In a preferred embodiment, the LAE ion-pair compound is in cosmetics group Closing the mass percent concentration in object is 0.0032-0.01%, 0.01-0.05%, 0.05-0.1%.

Term and definition:

Lauroyl arginine ethyl ester (Ethyl lauroylarginate, LAE) is one kind by fatty acid and binary amino acid Organic matter made of condensation is white hygroscopic solid, and chemical property is stablized in the range of pH3~7,50~58 DEG C of fusing point, should At a temperature of the LAE of 247g be dispersed in the water of 1kg, its distribution coefficient in water and in oil is greater than 10, that is, is primarily present in water Xiang Zhong.The study found that lauroyl arginine ethyl ester LAE have strong antibacterial, bio-toxicity is low, internal metabolic effects are good, with The high feature of Environmental compatibility.And wherein most representative feature is the metabolism noresidue of lauroyl arginine ethyl ester, correlation is ground Natural metabolism can quickly be carried out in human body and animal body by studying carefully display lauroyl arginine ethyl ester, generate lauric acid and arginine, Further it is metabolized as ornithine, urea, carbon dioxide and water.It is generated all in lauroyl arginine ethyl ester metabolic process Metabolite and final product be all it is nontoxic, with the metabolite phase of the food of humans and animals daily ingestion in vivo Together.

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 processing of acid, alkali, salt or esterified group is carried out to LEA, But the sulfonate groups of the creative antibacterial synergistic effect for selecting one kind that can enhance LAE, and the two is passed through unconventionally Intermolecular strong ionic bond is combined into new derivative, i.e. ion-pair compound, exists to improve LAE derivative significantly Purposes in cosmetic composition.

Technical effect

The advantages of cosmetic composition of the present invention, is:

Creativeness replaces bacteriostatic agent and preservative in cosmetic composition using LAE ion-pair compound, passes retaining It is also aobvious with fungistatic effect while the low in cost of cosmetic composition, the advantage that manufacture craft is simple, stability is good of uniting It writing, ingredient is single and preparation is simple, to no damage to human body, easily decomposes metabolism, 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 process of the invention, Condition, reagent, experimental method etc. are among the general principles and common general knowledge in the art in addition to what is specifically mentioned below, 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 configured to 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 the moon Osmanthus acyl arginine ethyl ester hydrochloride all dissolves, and lauroyl arginine ethyl ester hydrochloride aqueous solution (B) is made；Under the conditions of 90 DEG C Niacin sodium-salt aqueous solution (A) is slowly added into lauroyl arginine ethyl ester hydrochloride aqueous solution (B), is stirred continuously, reaction 2 Hour, it is cooled to room temperature, filters, precipitating is sufficiently washed with pure water, precipitate 60 DEG C of vacuum drying to get niacin ion pair chemical combination Object 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 of equivalent is stirred at room temperature until white solid is precipitated, and suction filtration is simultaneously washed with 30mL methanol in three times, obtains sodium tartrate Salt.Sodiotartrate is dissolved in 50mL water, is configured to sodium tartrate saline solution (A)；By lauroyl arginine ethyl ester hydrochloride 5.6g is dissolved in 40mL water, is heated to 90 DEG C, until lauroyl arginine ethyl ester hydrochloride all dissolves, lauroyl essence ammonia is made Acid ethyl ester hydrochloride saline solution (B)；Sodium tartrate saline solution (A) is slowly added into lauroyl arginine under the conditions of 90 DEG C It in ethyl ester saline solution (B), is stirred continuously, reacts 2 hours, be cooled to room temperature, filter, it is heavy sufficiently to be washed with pure water It forms sediment, 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；At 90 DEG C Under the conditions of oxalic acid sodium-salt aqueous solution (A) is slowly added into lauroyl arginine ethyl ester hydrochloride aqueous solution (B), constantly stir Mix, react 2 hours, be cooled to room temperature, filter, precipitating is sufficiently washed with pure water, precipitate 60 DEG C be dried in vacuo to get oxalic acid from Son 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 and original LAE and its hydrochloride are compared, and generate corresponding change, such as in pure water washing precipitating, dissolubility has changed, this explanation Strong interaction is produced between all protons and oxalic acid of lauroyl arginine ethyl ester, and is formd by strong ionic bond 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)；By the moon Osmanthus acyl arginine ethyl ester hydrochloride 4.0g is dissolved in 40mL water, is heated to 90 DEG C, until lauroyl arginine ethyl ester hydrochloride is complete Portion's dissolution, is 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 It is added in lauroyl arginine ethyl ester hydrochloride aqueous solution (B), is stirred continuously, react 2 hours, be cooled to room temperature, filter, use Pure water sufficiently washs precipitating, 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 and original LAE and its hydrochloride are compared, and generate corresponding change, this illustrates to generate between all protons of lauroyl arginine ethyl ester and carbonic acid Strong interaction, and form 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: lauroyl arginine ethyl ester hydrochloride (LAE) and above-mentioned prepared lauroyl arginine ethyl ester is organic Acid ion to respectively use (TSB) doubling dilution of trypticase soy broth at various concentration, drug and bacterium in 96 orifice plates In mix and be incubated for, separately set abacterial blank control culture medium C K1 and add the culture medium C K2 and not of LAE (1000 μ g/ml) The bacterium normal growth control medium CK3 of drug containing.96 orifice plates are put into be incubated in 37 DEG C of incubators and measure each hole afterwards for 24 hours Absorption photometric value at 625nm.With blank control OD₆₂₅It is worth consistent hole and is considered as bacterium without obvious growth.Bacterium is without obvious growth Drug minimum concentration be LAE to the minimal inhibitory concentration MIC (Minimal Inhibitory Concentration) of bacterium.

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

Compare	Escherichia coli	Staphylococcus aureus
			LAE	16	8
LAE niacin ion pair	16	4
			LAE tartaric acid ion pair	16	8
LAE oxalic ion pair	8	8
			LAE carbonate ions pair	16	16

Interpretation of result:

(1) LAE ion-pair compound it is most of to Escherichia coli keep identical antibacterial activity, especially LAE oxalic acid from Son rises the antibacterial activity of compound；

(2) LAE ion-pair compound is most of keeps identical antibacterial activity to staphylococcus aureus, LAE carbonic acid from Son declines the antibacterial activity of compound, and the antibacterial activity of LAE niacin ion-pair compound significantly rises；

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 staphylococcus aureus significant antibacterial Effect.

Embodiment eight: mould proof effect of the test LAE ion-pair compound to cosmetics

Principle

In this test simulation Cosmetic Manufacture and use process by the Potential feasibility of high-intensitive microbial contamination and Preservative is added in sample the optimum that microorganism grows in nature according to certain concentration, and can test to makeup Product product provides anti-corrosion effect.

1, prepare bacterium solution

By S. aureus Inoculate broth bouillon, 37 DEG C of cultures are for 24 hours.Aspergillus niger is inoculated with Cha Shi Liquid Culture Base, 25 DEG C of culture 6d.The two is configured to a certain amount of bacteria suspension respectively.

2, preparing cosmetics

It according to table 2, prepares make up remover (100ml), sets 6 formulas and a control altogether, wherein preservative is phenoxy group second Alcohol.Table 2

Note: LAE ion pair is LAE hydrochloric acid ion pair

3, inhibitory effect is tested

A certain amount of cosmetics are weighed, are inoculated with 10000 (cfu/g) staphylococcus aureuses and 1000000 (cfu/g) respectively Aspergillus niger after stirring, is placed 12h, 1d, 2d, 7d, 14d, 28d and is measured.Count of bacteria lecithin-tween Plain agar is used in 80- nutrient agar, control.As a result as shown in table 3-4.

Table 3

Table 4

Interpretation of result:

Fungistatic effect testing result is shown, in the LAE ion pair of 0.005-0.1% concentration range, is all generated to makeup remover Or it is basic generate expected anti-mold effect, wherein 0.01% and 0.05% anti-mold effect difference is less, slightly below 0.1% it is anti- Mould effect.

The control of preservative phenoxetol, only 0.5% concentration can generate anti-mold effect substantially, and 0.1% concentration Can not any effect be generated to cosmetics.In view of Phenoxyethanol be under intermediate concentration it is toxic, can be to brain and mind It is had an impact through system.Obviously its excessively high additive amount is compared, the LAE ion pair concentration range of 0.01%-0.05% has more Low human body is non-toxic, and more preferable to Bacteria suppression ability.

Negative water compares no any anti-mold effect.

Although in above-mentioned test, the fungistatic effect highest of 0.1% dosage group, and the patent Shen formerly submitted from applicant Please see (denomination of invention: " lauroyl arginine ethyl ester derivative and the purposes as animal antibacterial agent ", application number: 201810648982.3) from the point of view of test data, antibacterial effect is can be improved in LAE and its a certain range of dosage increasing of derivative Fruit, but the fungistatic effect relative to 0.05% dosage group does not increase significantly, illustrates the dosage range of 0.01%-0.05% Production needs are met.

In addition, according to the CTFA primary plus bacterium preservation challenge test recommended and evaluation criterion, test initial mould and The inoculum concentration of bacterium is respectively 10000 (cfu/g) and 1000000 (cfu/g), it is desirable that reduces by 90% in the 7th day mould, bacterium drop Low 99.9%, and mean continues to decline in 28 days, so that it may think that mould inhibitor has antimildew function to cosmetics.If mentioned The additive amount of high LAE and its derivative, although bacteriostasis rate correspondinglys increase, excessively high bacteriostasis rate means more residual, not Be conducive to human health.Even so, since the bacteriostatic agent of LAE and its derivative of the invention are nontoxic at natural environmental-protective is belonged to Ingredient, therefore the addition of high dose have using still than traditional chemicals bacteriostatic agent and mould inhibitor it is affine to human body close friend The advantages of.

Accordingly, it is considered to arrive production cost and needs of production, therefore LAE and its ion pair are as cosmetic composition The mass percent concentration of active constituent is 0.0030-0.01,0.01-1%, wherein preferred effective concentration is 0.01- 0.05%, most preferably 0.05% when can effectively it is mould proof, meet the needs of production.

Claims

1.LAE ion-pair compound is used to prepare the purposes of cosmetic composition, which is characterized in that the LAE ion pair chemical combination 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 organic acid is selected from niacin, tartaric acid, oxalic acid.

3. purposes as described in claim 1, which is characterized in that the cosmetic composition be face cream, toner, clarifying lotion, Make up remover, makeup lotion, facial mask, lipstick, mousse, nail polish.

4. purposes as described in claim 1, which is characterized in that the LAE ion-pair compound is in cosmetic composition Mass percent concentration is 0.0030-1%.

5. purposes as claimed in claim 4, which is characterized in that the LAE ion-pair compound is in cosmetic composition Mass percent concentration is 0.0030-0.01,0.01-1%.

6. purposes as claimed in claim 5, which is characterized in that the LAE ion-pair compound is in cosmetic composition Mass percent concentration is 0.0032-0.01%, 0.01-0.05%, 0.05-0.1%.

7. a kind of preparation method of cosmetic composition, which comprises the following steps:

(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 lauroyl arginine second shown in formula (III) Ester organic acid ion is 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 cosmetic composition, is sufficiently stirred, thus Obtain cosmetic 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. described in any item LAE ion-pair compounds containing claim 1-6 pass through side described in claim 7 or 8 The cosmetic composition that method is prepared, which is characterized in that it includes mass percent concentration be 0.0030-0.01,0.01- 1% LAE ion-pair compound.

10. cosmetic composition as claimed in claim 9, which is characterized in that it includes mass percent concentration be 0.0032- 0.01%, the LAE ion-pair compound of 0.01-0.05% or 0.05-0.1%.