KR20130048986A

KR20130048986A - Amphiphilic block copolymer, manufacturing method of the same, and cosmetic composition containing amphiphilic block copolymer

Info

Publication number: KR20130048986A
Application number: KR1020110113947A
Authority: KR
Inventors: 이현석; 김용진; 김도훈; 유재원; 이찬우; 김준오
Original assignee: (주)아모레퍼시픽
Priority date: 2011-11-03
Filing date: 2011-11-03
Publication date: 2013-05-13

Abstract

The present invention provides an amphiphilic block copolymer comprising a polyester as a hydrophobic block and a polyphosphoryl choline as a hydrophilic block, a preparation method thereof, and a cosmetic composition containing an amphiphilic block copolymer.

Description

Amphiphilic block copolymers, preparation methods thereof, and cosmetic compositions containing amphiphilic block copolymers {AMPHIPHILIC BLOCK COPOLYMER, MANUFACTURING METHOD OF THE SAME, AND COSMETIC COMPOSITION CONTAINING AMPHIPHILIC BLOCK COPOLYMER}

The present invention relates to an amphiphilic block copolymer, a method for preparing the same, and a cosmetic composition containing an amphiphilic block copolymer.

In the field of cosmetics and pharmaceuticals, there has been a need for the development of formulations that stably collect various agonists that are poorly soluble or unstable in the water. In order to overcome this problem, emulsion emulsion technology using nanoparticles or microparticles has been developed as a core technology for stabilization. In general, such an emulsification system uses a low molecular weight surfactant having a specific hydrophilic-hydrophobic ratio value to form fine emulsified particles, so that the fine particles containing the active ingredient tend to be unstable in the aqueous solution. In addition, since the emulsion film is very physicochemically weak, salts or charged organic matters are destroyed by contamination by inorganic substances, and the emulsion film is very weak against heat and light, and thus, there are many disadvantages in the long term storage.

To overcome these drawbacks, stabilization techniques using amphiphilic block polymers that can form more robust physicochemical interfacial films have been developed. Polymeric surfactants composed of hydrophilic blocks and hydrophobic blocks can be stably formed at the nano level by self-association force of the polymer itself without the addition of various additives and dispersants to overcome the insufficient colloidal stability. Amphiphilic block polymers composed of polyester polymer and PEG, a hydrophilic polymer, have been widely used as representative polymer surfactants, but for environmental reasons, the use of PEG-based raw materials is gradually limited.

As a raw material to replace PEG, MPC, a lipid-like substance containing phospholipid, which is a constituent of cell membrane, has been successfully synthesized recently, and based on high hydrophilicity and biocompatibility, it can be used for medical devices, drug delivery, and cosmetic surfactant. The desire to utilize is greatly increasing.

MPC, a biocompatible biomaterial, contains a vinyl group capable of polymerizing as well as phospholipids, and thus has a great advantage of preparing block polymers by polymerizing with other monomers. In fact, recently, a study has been introduced to prepare a block polymer combining PLA and MPC and use it as a carrier for drug delivery. However, ATRP (atom transfer radical polymerization) used in the polymerization of hydrophilic MPC with cyclic monomers of hydrophobic polyester series Synthesis is not suitable for cosmetic applications due to the complexity of synthesis and purification and the use of metal catalysts. Accordingly, there is an urgent need to develop an effective method for preparing a block polymer surfactant composed of an MPC block and a hydrophobic polyester block.

Japanese Laid-Open Patent No. 2004-137199

In order to solve the above problems, the present invention provides a novel amphiphilic block copolymer comprising a hydrophilic MPC block and a hydrophobic polyester block by using a RAFT polymerization method capable of precise control of molecular weight without a metal catalyst and a method of preparing the same. In addition, the amphiphilic block copolymer has the ability to form uniform microparticles through self-association and excellent emulsification performance, and thus, to provide a cosmetic composition having excellent emulsifying ability by containing an amphiphilic block copolymer. do.

In order to solve the above object, the present invention provides an amphiphilic block copolymer comprising a polyester as a hydrophobic block and a polyphosphoryl choline as a hydrophilic block.

In one embodiment of the present invention, the polyester (A) as a hydrophobic block and the polyphosphoryl choline (B) as a hydrophilic block may be of a bi-block type of A-B form.

In one embodiment of the present invention, the phosphoryl choline, the phosphorylcholine is 2-methacryloyloxyethyl phosphoryl choline (MPC), 2-bromoethoxyphenoxyphosphoryl meta At least one selected from the group consisting of 2-bromoethoxyphenoxyphosphoryl methacrylate, and 10-bisbenzyloxyphosphoryl oxydecyl methacrylate (10- [Bis (benzyloxy) phosphoryloxy] decyl methacrylate).

In one embodiment of the present invention, the polyphosphoryl choline may have a molecular weight of 1,000 to 100,000 Daltons.

In one embodiment of the present invention, the polyester is polycaprolactone, poly-L-lactic acid, poly-D, L-lactic acid, poly-D-lactic acid-co-glycolic acid, poly-L-lactic acid-co- At least one selected from the group consisting of glycolic acid, poly-D, L-lactic acid-co-glycolic acid, and copolymers thereof.

In one embodiment of the present invention, the polyester may have a molecular weight of 1,000 to 100,000 Daltons.

In one embodiment of the present invention, the weight ratio of the polyester and phosphoryl choline (phosphoryl choline) in the block copolymer may be 1: 9 to 9: 1.

In one embodiment of the present invention, the polyester is polycaprolactone, the phosphoryl choline is 2-methacryloyloxyethylphosphoryl choline, the block copolymer may be represented by the following formula (1).

[Formula 1]

(Wherein n and m are each independently an integer of 2 to 500.)

The present invention also provides a method for producing an amphiphilic block copolymer comprising living radical polymerization of phosphoryl choline and polyester.

In one embodiment of the present invention, the production method is to polymerize a polyester block through ring-opening polymerization;

Adding a nonmetallic chain transfer reagent to the polyester block; And

And adding a phosphoryl choline to the polyester block to which the non-metallic chain transfer reactant is bonded to polymerize the polyester-polyphosphorylcholine block copolymer by a living radical polymerization method.

In one embodiment of the present invention, the living radical polymerization may be RAFT (Reversible Addition-Fragmentation chain Transfer) method.

In one embodiment of the present invention, the polyester and phosphoryl choline (ester choline), ester bonds, unhydride bonds, carbamate bonds, carbonate bonds, imine bonds, amide bonds, secondary amine bonds, urethane bonds, It may be one or more bonds selected from the group consisting of phosphodiester bonds and hydrazone bonds.

In one embodiment of the present invention, the non-metallic chain transfer reaction agent may be 4-cyanopentanoic acid dithiobenzoate.

The present invention also provides a cosmetic composition containing the amphiphilic block copolymer.

According to the manufacturing method of the amphiphilic block copolymer of the present invention, unlike the conventional manufacturing method by using the RAFT polymerization method, the synthesis can be simplified, precise molecular weight control and uniform size distribution can be obtained. Amphiphilic block copolymers of the present invention can be used as a surfactant excellent in self-association force, emulsifying ability, moisturizing and hygroscopicity. This can be excellently applied to cosmetic compositions and the like.

1 is an average particle size distribution diagram of an amphiphilic block copolymer nanoparticles according to an embodiment of the present invention.

Hereinafter, preferred embodiments of the present invention will be described in detail in order to facilitate the present invention by those skilled in the art.

The present invention provides an amphiphilic block copolymer comprising a polyester as a hydrophobic block and a polyphosphoryl choline as a hydrophilic block.

The block copolymer may be composed of polyester (A) as a hydrophobic block and polyphosphorylcholine (B) as a hydrophilic block in a biblock form of AB form. Polyesters as hydrophobic blocks are biodegradable, and polyphosphorylcholine as hydrophilic blocks are biocompatible, including phospholipids.

Specifically, the production method of the present invention is to polymerize a polyester block through ring-opening polymerization; Adding a nonmetallic chain transfer reagent to the polyester block; And polymerizing the polyester-polyphosphorylcholine block copolymer by living radical polymerization by adding phosphoryl choline to the polyester block to which the non-metallic chain transfer reaction agent is bound.

Hereinafter, the manufacturing method of the amphiphilic block copolymer of this invention is described in detail.

First, the polyester block is polymerized by ring-opening polymerization.

In the present invention, the polyester is in the form of a ring (ring) is not limited if the compound capable of ring-opening polymerization, preferably polycaprolactone, poly-L- lactic acid, poly-D, L- lactic acid, poly-D-lactic acid at least one selected from the group consisting of -co-glycolic acid, poly-L-lactic acid-co-glycolic acid, poly-D, L-lactic acid-co-glycolic acid, and copolymers thereof. More preferably polycaprolactone. Polycaprolactone (PCL) is a kind of biodegradable polyester, which is polymerized through ring opening polymerization of ε-caprolactone.

The polyester may be used regardless of the molecular weight, the molecular weight is preferably 1,000 to 100,000 Daltons. If it is less than 1,000 Daltons, it is difficult to express the properties of the polymer as an oligomer, and if it is more than 100,000 Daltons, it is difficult to apply to cosmetic formulations because it has a low hydrophobicity and solubility in water.

Next, a non-metallic chain transfer reagent is added to the polyester block.

A non-metallic chain transfer reagent is bonded to the end of the polyester block to form a form capable of starting living radical polymerization. The nonmetallic chain transfer reaction agent is preferably 4-cyanopentanoic acid dithiobenzoate.

Finally, phosphoryl choline is added to the polyester block to which the non-metallic chain transfer reaction agent is bonded to polymerize the polyester-polyphosphorylcholine block copolymer by a living radical polymerization method.

In the present invention, the phosphorylcholine is not limited as long as it is a phosphorylcholine including a phospholipid having biocompatibility. Preferably, the phosphorylcholine is 2-methacryloyloxyethylphosphorylcholine (2-methacryloyloxyethyl phosphoryl). choline, MPC), 2-bromoethoxyphenoxyphosphoryl methacrylate, and 10-bisbenzyloxyphosphoryloxyldecyl methacrylate (10- [Bis (benzyloxy) phosphoryloxy] decyl methacrylate) It may be one or more selected from the group consisting of. More preferably, it may be 2-methacryloyloxyethyl phosphoryl choline (MPC).

The polyphosphoryl choline may be used regardless of molecular weight, but may have a molecular weight of 1,000 to 100,000 Daltons. If it is less than 1,000 Daltons, it is difficult to have the characteristics of the polymer as an oligomer, and if it is more than 100,000 Daltons, it is difficult to have an interfacial activity due to excessive hydrophilicity.

Phosphorylcholine added by a nonmetallic chain transfer reagent bound to the polyester block is block copolymerized.

The living radical polymerization may be a reversible addition-fragmentation chain transfer (RAFT) method. By the RAFT (Reversible Addition-Fragmentation Chain Transfer) method, it is possible to synthesize particles having precise molecular weight control and uniform distribution. This allows the carboxyl group located at the terminal of the non-metallic chain transfer reagent and the hydroxy group located at the terminal of the polyester to be bonded to each other by DCC coupling to form a polyester-RAFT conjugate, which itself polymerizes phosphorylcholine. This is because it can be used as a macro-RAFT reagent.

The above-mentioned preparation method forms a polyester-polyphosphorylcholine amphiphilic block copolymer. At this time, the weight ratio of the polyester and phosphoryl choline (phosphoryl choline) may be 1: 9 to 9: 1. If the amount of the polyester exceeds the above range, there is a problem that it does not form a stable association and precipitates. If the amount of the phosphorylcholine exceeds the above range, it is dissolved directly in the aqueous solution. there is a problem.

The polyester and phosphorylcholine (phosphoryl choline) is not limited to covalent bonds, for example, ester bonds, unhydride bonds, carbamate bonds, carbonate bonds, imine bonds, amide bonds, secondary amine bonds, urethanes It may be one or more bonds selected from the group consisting of bonds, phosphodiester bonds and hydrazone bonds.

Amphiphilic block copolymers according to the present invention is a novel amphiphilic block copolymer, comprising polycaprolactone as a hydrophobic block and 2-methacryloyloxyethylphosphorylcholine as a hydrophilic block, represented by the following formula (1) It may be.

[Formula 1]

(Wherein n and m are each independently an integer of 2 to 500.)

Amphiphilic block copolymer according to the present invention is excellent in the self-association force can form a polymer assembly through self-association. As a method of forming a polymer assembly in an aqueous solution using the biodegradable block copolymer proposed in the present invention, a method of dispersing the biodegradable block copolymer polymer directly in an aqueous solution and then applying ultrasonic waves, and dispersing the polymer in an organic solvent Or dissolving and then evaporating or evaporating the organic solvent with excess water, dispersing or dissolving the polymer in the organic solvent, vigorously stirring using a homogenizer or a high pressure emulsifier and evaporating the solvent, dispersing the polymer in the organic solvent or After dissolving, there is a method of dialysis with an excess of water, a method of dispersing or dissolving a polymer in an organic solvent, and then gradually adding water.

The polymer assembly formed by the amphiphilic block copolymer according to the present invention may form nano-sized particles to carry an active ingredient therein. This self-association force has the ability to form uniform fine particles and excellent emulsification performance, and thus can be stably dispersed in the water phase. It is therefore suitable as a biocompatible polymer surfactant.

The present invention also provides a cosmetic composition containing the amphiphilic block copolymer. The amphiphilic block copolymer is preferably contained 0.1 to 5% by weight based on the total weight of the composition. If it is less than 0.1% by weight, it is difficult to expect the required emulsifying performance, and if it is more than 5% by weight, a rough feeling peculiar to a polymer may appear.

The cosmetic composition according to the present invention can be solubilized various bioactive components using the amphiphilic block polymer to be stably dispersed in the water phase. That is, the composition may have excellent stability while using a biocompatible and biodegradable harmless surfactant.

The cosmetic composition of the present invention is not particularly limited in formulation, and may be appropriately selected as desired. For example, skin lotion, skin softener, skin toner, astringent, lotion, milky lotion, moisturizing lotion, nutrition lotion, massage cream, nutritional cream, moisturizing cream, hand cream, foundation, essence, nutrition essence, pack, soap, cleansing But the present invention is not limited thereto, and may be manufactured by any one or more formulations selected from the group consisting of a foam, a cleansing lotion, a cleansing cream, a body lotion and a body cleanser.

When the formulation of the present invention is a paste, cream or gel, animal fiber, plant fiber, wax, paraffin, starch, tracant, cellulose derivative, polyethylene glycol, silicone, bentonite, silica, talc or zinc oxide may be used as the carrier component .

When the formulation of the present invention is a powder or a spray, lactose, talc, silica, aluminum hydroxide, calcium silicate or polyamide powder may be used, and especially in the case of spray, additionally chlorofluorohydrocarbon, propane Propellant such as butane or dimethyl ether.

In the case of the solution or emulsion of the present invention, a solvent, a solvent or an emulsifier is used as a carrier component, and examples thereof include water, ethanol, isopropanol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, propylene glycol, , 3-butyl glycol oil, glycerol aliphatic ester, polyethylene glycol or sorbitan fatty acid esters.

When the formulation of the present invention is a suspension, a carrier such as water, a liquid diluent such as ethanol or propylene glycol, a suspending agent such as ethoxylated isostearyl alcohol, polyoxyethylene sorbitol ester and polyoxyethylene sorbitan ester, Cellulose, aluminum metahydroxide, bentonite, agar or tracant, etc. may be used.

When the formulation of the present invention is a cleansing agent, as a carrier component, an aliphatic alcohol sulfate, an aliphatic alcohol ether sulfate, a sulfosuccinic acid monoester, isethionate, an imidazolinium derivative, a methyltaurate, a sarcosinate, a fatty acid amide ether sulfate, an alkyl Amidobetaines, fatty alcohols, fatty acid glycerides, fatty acid diethanolamides, vegetable oils, linolin derivatives or ethoxylated glycerol fatty acid esters and the like can be used.

The cosmetic composition may further contain ingredients included in a functional additive and a general cosmetic composition. The functional additives may include water-soluble vitamins, oil-soluble vitamins, polymer peptides, polymeric polysaccharides, sphingolipids and seaweed extracts.

In addition to the said functional additive, you may mix | blend the component contained in a general cosmetic composition with the cosmetic composition of this invention as needed. In addition to the other components included, oils and fats, moisturizers, emollients, surfactants, organic and inorganic pigments, organic powders, ultraviolet absorbers, preservatives, fungicides, antioxidants, plant extracts, pH adjusters, alcohols, pigments, flavorings, blood circulation And accelerators, cooling agents, limiting agents, purified water, and the like.

The present invention is described in more detail through the following implementation. However, the examples are for illustrating the present invention, and the scope of the present invention is not limited thereto.

Example 1 Preparation of Polycaprolactone-Polymethacryloyloxyethylphosphorylcholine Block Copolymer (PCL-b-PMPC)

1-1. Polycaprolactone (PCL) Block Production through Ring Opening Polymerization

Raw material name Content (g, ml) 1.ε-caprolactone monomer 10 g 2. Butanol 0.1 ml 3.Octanoic acid tin (Tin (Ⅱ) 2-ethylhexanoate) 0.01 g

Manufacturing method

1) The raw materials 1 to 3 of Table 1 were added to the dried 250 ml flask, a magnetic bar was added, a condenser was connected, and a vacuum was added three times.

2) The flask was sealed and placed in an oil bath at 110 ° C. for polymerization for 24 hours while stirring.

3) After the polymerization was completed, the temperature was lowered to room temperature, completely dissolved in methylene chloride, and then precipitated in excess methanol. This process was repeated three times to remove unreacted monomers and oligomers.

The sample obtained after precipitation was dried under reduced pressure at room temperature for 12 hours or more to obtain 8.8 g of a polycaprolactone polymer (PCL-OH) having a hydroxyl group bonded to one end. Hydrogen nuclear magnetic resonance analysis confirmed that the number average molecular weight is 9,000 Da, and the amount of the remaining monomer or catalyst is negligible.

1-2. Coupling nonmetallic chain transfer reagent to PCL-OH end by DCC coupling

Raw material name Content (g, ml) 1.PCL-OH (Prepared in Example 1-1) 5 g 2. 4-Cyanopentanoic acid dithiobenzoate (non-metal chain transfer reagent) 0.3 g DCC ( N, N′- Dicyclohexylcarbodiimide) 0.1 ml 4.DMAP (4- (Dimethylamino) pyridine) 0.01 g 5. Methylene chloride 100 ml

Manufacturing method

1) To the dried 250ml flask, the raw materials 1 to 5 of Table 2 were added, a magnetic bar was put in, a condenser was connected, and a vacuum was added three times.

2) The flask was sealed and the coupling reaction proceeded for 48 hours while stirring at room temperature.

3) After the reaction was completed, the temperature was lowered to room temperature, completely dissolved in methylene chloride, and then precipitated in excess methanol. This process was repeated three times to remove unreacted monomers and oligomers.

The sample obtained after precipitation was dried under reduced pressure at room temperature for at least 12 hours to obtain 4.5 g of a polymer (PCL-RAFT) having a non-metallic chain transfer reagent coupled to one end. Hydrogen nuclear magnetic resonance analysis confirmed that the coupling degree of the nonmetallic chain transfer reagent was 67%.

1-3. Preparation of Polycaprolactone-Polymethacryloyloxyethylphosphorylcholine Block Copolymer (PCL-b-PMPC) by RAFT Polymerization

Raw material name Content (g, ml) 1.PCL-RAFT (Prepared in Example 1-2) 3 g 2.MPC (2-METHACRYLOYLOXYETHYL PHOSPHORYL CHOLINE) 4.5 g ACPA (4,4'-Azobis (4-cyanopentanoic acid), initiator) 8 ml 4. Dimethyl Sulfoxide 50 ml 5. Ethanol 50 ml

Manufacturing method

1) The raw materials 1 to 5 of Table 3 were added to the dried 250 ml flask, a magnetic bar was added, a condenser was connected, and a vacuum was added three times.

2) The flask was sealed and proceeded with RAFT polymerization for 24 hours while stirring at 70 ° C.

3) After the reaction was completed, the temperature was lowered to room temperature, and then precipitated in excess ethyl ether. This process was repeated three times to remove unreacted monomers and remaining oligomers.

The sample obtained after precipitation was dried under reduced pressure at room temperature for 12 hours or more to obtain 6.2 g of a block polymer (PCL-b-PMPC) consisting of polycaprolactone and polymethacryloyloxyethylphosphorylcholine (Formula 1). Hydrogen nuclear magnetic resonance analysis confirmed that the number average molecular weight is 28,000 Da, the block ratio of PCL and PMPC is 1: 2.

[Formula 1]

Wherein n is 74 and m is 48.

Comparative Example 1 Preparation of Polycaprolactone-Block-Polyethylene Glycol Copolymer (PCL-b-PEG)

Raw material name Content (g, ml) Monomethoxy polyethylene glycol 10 g 2. ε-caprolactone monomer 10 g 3.Octanoic acid tin (Tin (Ⅱ) 2-ethylhexanoate) 0.05 g

Manufacturing method

1) Into a dried 50 mL flask, the magnetic bars coated with the raw materials 1 to 3 and Teflon of Table 4 were put in a vacuum for 30 minutes, and then sealed.

2) The sealed flask was placed in an oil bath at 150 ° C. and polymerization was performed for about 6 hours.

3) The mixed solution in the flask after polymerization was completely dissolved by adding 20 mL of methylene chloride as a solid solid phase, and then precipitated in excess ethyl ether. This process was repeated three times to remove unreacted monomers and oligomers.

The sample obtained by precipitation was dried under reduced pressure at room temperature for 12 hours to finally obtain 17.3 g of a polycaprolactone-block-polyethylelllycol block copolymer (PCL-b-PEG). Hydrogen nuclear magnetic resonance analysis confirmed that caprolactone was ring-opened at the terminal of monomethoxypolyethylene glycol to form a copolymer. It was confirmed that the number average molecular weight was about 9,200 Da through the integral ratio of the peaks corresponding to monomethoxy polyethylene glycol and polycaprolactone.

Examples 2 to 5 Preparation of Nanoparticles

Nanoparticles were prepared by incorporating Compound K, which is one of ginseng saponin derivatives, into the amphiphilic block polymer (PCL-b-PMPC) having self-association prepared in Example 1. Example 1 (PCL-b-PMPC) and compound K were added to 50 g of ethanol in the amounts shown in Table 5, respectively, and stirred to dissolve uniformly. After checking that dissolved, it was slowly added to 50 g of distilled water and stirred. The mixture was stirred for about 1 minute and the ethanol was evaporated while warming to 50 to 60 ° C., and finally a nanoparticle dispersion containing Compound K (Examples 2 to 5) was prepared. In addition, nanoparticle dispersion (Comparative Example 2) was prepared in the same manner by adding Comparative Example 1 (PCL-b-PEG) instead of Example 1.

ingredient Example 2 Example 3 Example 4 Example 5 Comparative Example 2 Example 1 (PCL-b-PMPC) 0.5 g 0.5 g 0.5 g 0.5 g - Compound K 0.1 g 0.25 g 0.4g 0.5 g 0.5 g Comparative Example 1 (PCL-b-PEG) - - - - 0.5 g

Test Example 1 Measurement of Size by Dynamic Light Scattering of Nanoparticles

The average particle size of the nanoparticles prepared in Examples 2 to 5 and Comparative Example 2 was measured using Zetasizer Nano ZS of Malvern, UK. The scattering angle was measured at 90 ° and the temperature was maintained at 25 ° C., and the results are shown in Table 6 below, and the particle size distribution of Example 2 is shown in FIG. 1.

Test substance Average particle size (nm) Critical micelle formation capacity (CMC) Example 2 66.0 4.68E-04 Example 3 68.1 4.11E-04 Example 4 75.2 4.32E-04 Example 5 88.5 3.89E-04 Comparative Example 2 120.0 6.15E-04

As can be seen in Table 6 and Figure 1, it was confirmed that the nanoparticle size of Examples 2 to 5 is smaller than that of Comparative Example 2, the CMC is smaller, particles of more uniform size are formed.

Formulation Example 1 Oil-In-Water Emulsifier

The composition of the oil-in-water emulsifier type containing the amphiphilic block polymer (PCL-b-PMPC) prepared in Example 3 is shown in Table 7 (unit: wt%).

ingredient content Cetearyl Alcohol (CETOS KD) One Hydrogenated C6-14 Olefin Polymer (Puresyn 4) 10 Triethanolamine (TEA) 0.08 Carbopol (Carbopol 981 (1%)) 8 Methyl paraben (DANISOL-M) 0.2 Prop paraben (DANISOL- P) 0.1 Distilled water Balance Example 3 (PCL-b-PMPC) 0.4 Sum 100

Claims

An amphiphilic block copolymer comprising a polyester as a hydrophobic block and a polyphosphoryl choline as a hydrophilic block.

The method of claim 1,
The phosphorylcholine is 2-methacryloyloxyethyl phosphoryl choline (MPC), 2-bromoethoxyphenoxyphosphoryl methacrylate (2-Bromoethoxyphenoxyphosphoryl methacrylate), and 10-bisbenzyl At least one amphiphilic block copolymer selected from the group consisting of oxyphosphoryl oxydecyl methacrylate (10- [Bis (benzyloxy) phosphoryloxy] decyl methacrylate).

The method of claim 1,
The polyester is polycaprolactone, poly-L-lactic acid, poly-D, L-lactic acid, poly-D-lactic acid-co-glycolic acid, poly-L-lactic acid-co-glycolic acid, poly-D, L- At least one amphiphilic block copolymer selected from the group consisting of lactic acid-co-glycolic acid and copolymers thereof.

The method of claim 1,
The block copolymer includes polycaprolactone as a hydrophobic block and 2-methacryloyloxyethylphosphorylcholine as a hydrophilic block, and is represented by the following formula (1).
[Formula 1]

(Wherein n and m are each independently an integer of 2 to 500.)

The method of claim 1,
Amphiphilic block copolymer in which the polyester (A) as said hydrophobic block and the polyphosphorylcholine (B) as a hydrophilic block are comprised in the biblock type of AB form.

The method of claim 1,
The polyphosphoryl choline is an amphiphilic block copolymer having a molecular weight of 1,000 to 100,000 Daltons.

The method of claim 1,
The polyester is an amphiphilic block copolymer having a molecular weight of 1,000 to 100,000 Daltons.

The method of claim 1,
Amphiphilic block copolymer of the weight ratio of the polyphosphoryl choline (polyphosphoryl choline) and polyester in the block copolymer is 1: 9 to 9: 1.

A method for producing an amphiphilic block copolymer comprising living radical polymerization of polyester and phosphoryl choline.

The method of claim 9,
The production method is to polymerize a polyester block through ring-opening polymerization;
Adding a nonmetallic chain transfer reagent to the polyester block; And
Amphiphilic block comprising a; polymerizing a polyester-polyphosphorylcholine block copolymer by living radical polymerization by adding phosphoryl choline to the polyester block to which the nonmetallic chain transfer reaction agent is bound; Method of Preparation of Copolymer.

11. The method according to claim 9 or 10,
The living radical polymerization is a method of producing an amphiphilic block copolymer of RAFT (Reversible Addition-Fragmentation chain Transfer) method.

The method of claim 9,
The phosphorylcholine is 2-methacryloyloxyethyl phosphoryl choline (MPC), 2-bromoethoxyphenoxyphosphoryl methacrylate (2-Bromoethoxyphenoxyphosphoryl methacrylate), and 10-bisbenzyl A method for producing at least one amphiphilic block copolymer selected from the group consisting of oxyphosphoryl oxydecyl methacrylate (10- [Bis (benzyloxy) phosphoryloxy] decyl methacrylate).

The method of claim 9,
The polyester is polycaprolactone, poly-L-lactic acid, poly-D, L-lactic acid, poly-D-lactic acid-co-glycolic acid, poly-L-lactic acid-co-glycolic acid, poly-D, L- A process for producing at least one amphiphilic block copolymer selected from the group consisting of lactic acid-co-glycolic acid and copolymers prepared from monomers thereof.

The method of claim 9,
The polyester is polycaprolactone, the phosphoryl choline is 2-methacryloyloxyethylphosphoryl choline, and the block copolymer is represented by the following formula (1).
[Formula 1]

(Wherein n and m are each independently an integer of 2 to 500.)

The method of claim 9,
The polyphosphoryl choline is a method of producing an amphiphilic block copolymer having a molecular weight of 1,000 to 100,000 Daltons.

The method of claim 9,
The polyester is a method of producing an amphiphilic block copolymer having a molecular weight of 1,000 to 100,000 Daltons.

The method of claim 9,
Method of producing an amphiphilic block copolymer of the weight ratio of the polyester and phosphoryl choline (phosphoryl choline) in the block copolymer is 1: 9 to 9: 1.

The method of claim 9,
The polyester and phosphoryl choline (ester choline) is an ester bond, an unhydride bond, a carbamate bond, a carbonate bond, an imine bond, an amide bond, a secondary amine bond, a urethane bond, a phosphodiester bond and a hydrazone bond Method for producing an amphiphilic block copolymer that is combined with one or more selected from the group consisting of.

The method of claim 10,
The non-metallic chain transfer reaction agent is a 4-cyanopentanoic acid dithiobenzoate.

Cosmetic composition containing the amphiphilic block copolymer of any one of Claims 1-8.

The method of claim 20,
The amphiphilic block copolymer is contained in a cosmetic composition of 0.1 to 5% by weight based on the total weight of the composition.