KR20230085970A - Preparing method of dextrin polysaccharide polymeric derivatives - Google Patents

Abstract

The present invention discloses a method for preparing a dextrin polysaccharide polymer derivative.
Since the method for producing dextrin ester of the present invention does not use toxic substances, environmental damage can be reduced, worker safety can be guaranteed, and damage caused by residual solvent can be reduced.
In addition, the transparency of oil gel prepared by using the dextrin ester as a final compound may be improved.

Description

Method for preparing dextrin polysaccharide polymer derivatives {PREPARING METHOD OF DEXTRIN POLYSACCHARIDE POLYMERIC DERIVATIVES}

The present invention relates to a method for preparing a dextrin polysaccharide polymer derivative, and more specifically, to a method for preparing a dextrin ester, which is an example of a dextrin polysaccharide polymer derivative, using a reaction solvent that is improved from conventional reaction solvents.

Dextrin ester, which is an example of a dextrin polysaccharide polymer derivative, is an oil gelling agent that is used to impart viscosity to oily emollients in cosmetics or to prepare a gel form, and also to improve the feeling of use.

In particular, when oil is gelled using dextrin ester, product formulation researchers want not to harm the transparency of the oil gel, and not to harm the spreadability and moisturizing power. For this reason, the physical properties of dextrin esters that maintain the transparency of oil gels can be judged as a measure of luxury, so dextrin esters that support high-transparency gels are preferred.

Dextrin ester is prepared by reacting dextrin and acyl chloride, and in the synthesis process, the reaction solvent and reaction catalyst determine the degree of reactivity and reaction yield, and determine the physical properties of the final dextrin ester.

U.S. Patent No. 5,840,883 discloses formamides, for example, dimethylformamide and acetamide, as well as ketone compounds and aromatic compounds as reaction solvents, and U.S. Patent Publication 2005/0019296 discloses N-methyl-2-pyrrolidone. this was used

Conventional inventions mainly used N-methyl-2-pyrrolidone or dimethylformamide as a reaction solvent, but these reaction solvents are classified as toxic substances and have severe regulatory characteristics. In particular, since several tens of ppm to thousands of ppm of the reaction solvent remain in the dextrin ester after the reaction, the harmfulness of these residual solvents sometimes affects the overall quality of cosmetic materials.

Therefore, it is necessary to research and develop methods for preparing dextrin esters that can be applied as safe and high-quality cosmetic materials.

US registered patent 5,840,883 US Patent Publication 2005/0019296

Therefore, when the present inventors of the present invention use N-ethyl-2-pyrrolidone as a reaction solvent when preparing dextrin ester, it is very safe because the reaction solvent does not remain, and the dextrin ester produced by synthesizing the dextrin ester as a solvent The present invention was completed by finding that the transparency of an oil gel prepared by using as a final compound was improved.

Therefore, a specific problem of the present invention is to provide a method for preparing a dextrin ester using N-ethyl-2-pyrrolidone as a reaction solvent.

In order to solve the above problems, the present invention discloses the following means.

Specifically, the present invention discloses a method for preparing a dextrin ester represented by Chemical Formula 1 by reacting dextrin with an acyl chloride represented by Chemical Formula 2 in the presence of N-ethyl-2-pyrrolidone as a reaction solvent.

Since the method for preparing the dextrin ester of the present invention does not use toxic substances, it can reduce environmental damage and ensure the safety of workers.

In addition, it is possible to reduce damage caused by residual solvents that remain in a small amount.

In addition, the transparency of oil gel prepared by using the produced dextrin ester as a final compound may be improved.

The dextrin ester thus synthesized can be used to impart viscosity to oily emollients or to prepare a gel form when applied to cosmetics.

The effects of the present invention are not limited to the effects mentioned above, and various effects may be included within a range apparent to those skilled in the art from the contents to be described below.

Hereinafter, the present specification will be described in more detail.

A detailed description of this is as follows. Meanwhile, each description and embodiment disclosed in the present invention may also be applied to other descriptions and embodiments for each. That is, all combinations of the various elements disclosed herein fall within the scope of the present invention. In addition, it cannot be seen that the scope of the present invention is limited by the specific descriptions described below.

Expressions such as “comprising” used in this specification are understood as open-ended terms that include the possibility of including other embodiments, unless specifically stated otherwise in a phrase or sentence in which the expression is included. It should be.

The terms or words used in the description and claims of the present invention should not be construed as being limited to ordinary or dictionary meanings, and the inventors use the concept of terms appropriately in order to explain their invention in the best way. Based on the principle that it can be defined, it should be interpreted as meaning and concept consistent with the technical spirit of the present invention.

Manufacturing method of dextrin ester

The present invention provides a method for preparing a dextrin ester represented by Chemical Formula 1 by reacting dextrin with an acyl chloride represented by Chemical Formula 2 in the presence of N-ethyl-2-pyrrolidone as a reaction solvent.

[Formula 1]

[Formula 2]

In Formula 1,

A is hydrogen or (C=O)-R';

In this case, R' is a substituted or unsubstituted straight-chain or branched alkyl group having 3 to 25 carbon atoms,

n is an integer from 1 to 20;

In Formula 2,

R is a straight-chain or branched alkyl group having 3 to 25 carbon atoms.

In the present invention, the term “dextrin” generically refers to polysaccharides having a molecular weight smaller than that of starch, and has a structure of (C ₆ H ₁₀ O ₅ ) _n .

In the present invention, the term "acyl chloride" is a derivative having a structure in which OH of carboxylic acid is substituted with Cl, and when Cl is released and exists as an anion, it is stable and thus a nucleophilic acyl substitution reaction is possible.

In the present invention, the method for preparing dextrin ester is a reaction in which (C=O)-R bonds to an OH group of polysaccharide dextrin by a nucleophilic acyl substitution reaction between dextrin, which is a polysaccharide, and acyl chloride to form an ester group, wherein the ester group is There are three OH groups that can be bonded, and among them, dextrin ester is prepared by combining two or more groups.

In the present invention, the term "dextrin ester" is a polysaccharide polymer used to impart viscosity to oily emollients in cosmetics or to prepare a gel form. Specifically, it is a material that connects a fatty acid ester to a polysaccharide dextrin, and a reaction solvent and a reaction catalyst are very important in the synthesis process. Specifically, the reaction solvent affects not only the reaction yield but also the physical properties of the final product dextrin ester. In particular, dextrin ester makes oil into gel, and the transparency of gel oil is also an important property, and the choice of reaction solvent affects this transparency.

In general, dimethylformamide and N-methyl-2-pyrrolidone are often used as reaction solvents, and most of them correspond to toxic substances. Therefore, it is intended to solve problems that have not been solved in the past by using N-ethyl-2-pyrrolidone, which has no harmful controversy, as a reaction solvent.

In the present invention, the method for preparing the dextrin ester may be performed in the presence of a catalyst, but is not limited thereto.

In the present invention, the catalyst may be any one of 3-picoline or pyridine, but is not limited thereto.

Specifically, the reaction catalyst affects the physical properties of the final product dextrin ester as well as the reaction yield like the reaction solvent. The catalysts, 3-picoline and pyridine, are catalysts that play a role in reducing damage to the human body and the environment by preventing harmful or toxic substances from being generated, and transparency is improved when dextrin esters prepared using these catalysts are used in oil emollients. has the effect of

In the present invention, in Formula 1, A is hydrogen or (C=O)-R', where R' is a substituted or unsubstituted straight-chain or branched alkyl group having 7 to 21 carbon atoms, and n is 1 to 10 It may be an integer of 12, but is not limited thereto.

In the present invention, in Formula 1, n means an average degree of polymerization.

In the present invention, in Formula 2, R may be a substituted or unsubstituted straight-chain or branched alkyl group having 7 to 21 carbon atoms, but is not limited thereto.

In the present invention, the acyl chloride represented by Chemical Formula 2 may be any one or more of the compounds represented by Chemical Formulas 2-1 to 2-6 below, but is not limited thereto.

[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Formula 2-4]

[Formula 2-5]

[Formula 2-6]

In the compound represented by Formula 2-5, p and q are each independently an integer of 0 to 13, and the sum of p and q is 13.

In the present invention, the compound represented by Formula 2-1 is ethylhexanoyl chloride, and the compound represented by Formula 2-2 is lauroyl chloride, represented by Formula 2-3 The compound is myristoyl chloride, the compound represented by Formula 2-4 is palmitoyl chloride, and the compound represented by Formula 2-5 is typically isostearoyl chloride (Isostearoyl chloride). ), and the compound represented by Formula 2-6 is behenoyl chloride.

In the present invention, the dextrin ester represented by Formula 1 is dextrin laurate, dextrin myristate, dextrin palmitate, dextrin behenate, dextrin palmitate/ It may be any one selected from the group consisting of ethyl hexanoate (Dextrin Palmitate/Ethyl Hexanoate) and dextrin isostearate (Dextrin Isostearate), but is not limited thereto.

In the present invention, the dextrin and the acyl chloride represented by Formula 2 may be reacted at a weight ratio of 1:2.9 to 5.8, but is not limited thereto.

Example

ingredient

Raw materials used in the following Examples and Comparative Examples were purchased from Sigma-Aldrich Korea and TCI.

Preparation Example 1: Preparation of palmitoyl chloride

After adding 56 g of thionyl chloride to a reactor equipped with a reflux condenser and raising the temperature to 75° C. using an oil bath, 100 g of palmitic acid was slowly added for 1 hour. After the addition was completed, the reaction was maintained for 90 minutes, and then the temperature was raised to 100 ° C. and distilled to collect the reaction solution.

Then, the collected reaction solution was used after increasing the purity using a vigreux column.

Preparation Example 2: Preparation of ethylhexanoyl chloride

After adding 96 g of thionyl chloride and raising the temperature to 75° C. using an oil bath, 100 g of 2-ethylhexanoic acid was slowly added for 1 hour. After the addition was completed, the reaction was maintained for 90 minutes, and then the temperature was raised to 100 ° C. and distilled to collect the reaction solution.

Then, the collected reaction solution was used after increasing the purity using a vigreux column.

Preparation Example 3: Preparation of isostearoyl chloride (Isostearoyl chloride)

After adding 56 g of thionyl chloride and raising the temperature to 75° C. using an oil bath, 100 g of isostearic acid was slowly added for 1 hour. After the addition was completed, the reaction was maintained for 90 minutes, and then the temperature was raised to 100 ° C. and distilled to collect the reaction solution.

Then, the collected reaction solution was used after increasing the purity using a vigreux column.

Palmitoyl chloride, ethylhexanoyl chloride, and isostearoyl chloride prepared by the above method were used as starting materials for dextrin ester synthesis, and the synthesis and measurement values through this It is the same as the following Examples and Comparative Examples.

Example 1. Preparation of Dextrin Palmitate

Using a 500 mL separate reactor equipped with a stirrer, thermometer and cooling tube, 35 g of N-ethyl-2-pyrrolidone as a reaction solvent, 55 g of 3-picoline as a catalyst, and 17.8 g of dextrin as a starting material (DE = 11, number average molecular weight = 1700, average degree of polymerization (n) = 10) was added, and the temperature was raised to 60 ° C. to dissolve completely. Thereafter, 40 g of 3-picoline was separately added to the above reactor, and then 91 g of palmitoyl chloride prepared according to Preparation Example 1 was slowly added. After completion of the addition, the temperature was raised to 80 ° C. and reacted for 4 hours. Thereafter, after slowly cooling to 50 ° C, 270 g of methanol was added and cooled to 25 ° C to proceed with precipitation. After filtering the reaction product, homogenization was performed using a mixed solution of acetone/water (volume ratio: 7:3), and after neutralization, washing was performed twice with acetone. The reaction product was vacuum dried at 50° C. for 1 day to obtain 90 g of dextrin palmitate.

Example 2. Preparation of Dextrin Palmitate

35 g of N-ethyl-2-pyrrolidone as a reaction solvent, 46.7 g of pyridine as a catalyst, and 17.8 g of dextrin as a starting material (DE = 11, number average molecular weight = 1700, average degree of polymerization (n) = 10) was added, and the temperature was raised to 60° C. to dissolve completely. Thereafter, 33 g of pyridine was separately added to the above reactor, and then 91 g of palmitoyl chloride prepared according to Preparation Example 1 was slowly introduced. After completion of the addition, the temperature was raised to 80 ° C. and reacted for 4 hours. Thereafter, after slowly cooling to 50 ° C, 270 g of methanol was added and cooled to 25 ° C to proceed with precipitation. After filtering the reaction product, homogenization was performed using a mixed solution of acetone/water (volume ratio: 7:3), and after neutralization, washing was performed twice with acetone. The reaction product was vacuum dried at 50° C. for one day to obtain 89 g of dextrin palmitate.

Example 3. Preparation of Dextrin Palmitate/Ethyl Hexanoate (Ratio of 27:10)

Using a 500 ml separate reactor equipped with a stirrer, thermometer and cooling tube, 35 g of N-ethyl-2-pyrrolidone as a reaction solvent, 55 g of 3-picoline as a catalyst, and 17.8 g of dextrin as a starting material (DE = 11, number average molecular weight = 1700, average degree of polymerization (n) = 10) was added and the temperature was raised to 60 ° C to completely dissolve. Thereafter, 40 g of 3-picoline was separately added to the above reactor, and then 75 g of palmitoyl chloride prepared according to Preparation Example 1 and 17 g of ethylhexanoyl chloride prepared according to Preparation Example 2 were slowly added. put in After completion of the addition, the temperature was raised to 80 ° C. and reacted for 4 hours. Thereafter, after slowly cooling to 50 ° C, 270 g of methanol was added and cooled to 25 ° C to proceed with precipitation. After filtering the reaction product, homogenization was performed using a mixture of acetone/water 7:3 (volume ratio: 7:3), neutralization was performed, and washing was performed twice with acetone. The reaction product was vacuum dried at 50° C. for one day to obtain 85 g of dextrin palmitate/ethyl hexanoate.

Example 4. Preparation of Dextrin Palmitate/Ethyl Hexanoate (Ratio of 27:10)

35 g of N-ethyl-2-pyrrolidone as a reaction solvent, 46.3 g of pyridine as a catalyst, and 17.8 g of dextrin as a catalyst (DE= 11, number average molecular weight = 1700, average degree of polymerization (n) = 10) was added, and the temperature was raised to 60 ° C to completely dissolve. Thereafter, 33 g of pyridine was separately added to the reactor, and then 75 g of palmitoyl chloride prepared according to Preparation Example 1 and 17 g of ethylhexanoyl chloride prepared according to Preparation Example 2 were slowly added. After completion of the addition, the temperature was raised to 80 ° C. and reacted for 4 hours. Thereafter, after slowly cooling to 50 ° C, 270 g of methanol was added and cooled to 25 ° C to proceed with precipitation. After filtering the reaction product, homogenization was performed using a mixture of acetone/water 7:3 (volume ratio: 7:3), neutralization was performed, and washing was performed twice with acetone. The reaction product was vacuum dried at 50° C. for one day to obtain 85 g of dextrin palmitate/ethyl hexanoate.

Example 5. Preparation of Dextrin Isostearate

Using a 500 mL separate reactor equipped with a stirrer, thermometer and cooling tube, 35 g of N-ethyl-2-pyrrolidone as a reaction solvent, 55 g of 3-picoline as a catalyst, and 17.8 g of dextrin as a starting material (DE = 11, number average molecular weight = 1700, average degree of polymerization (n) = 10) was added and the temperature was raised to 60 ° C to completely dissolve. Then, 40 g of 3-picoline was separately added to the above reactor, and then 99 g of isostearoyl chloride prepared according to Preparation Example 3 was slowly added. After completion of the addition, the temperature was raised to 80 ° C. and reacted for 4 hours. Thereafter, after slowly cooling to 50 ° C, 270 g of methanol was added and cooled to 25 ° C to proceed with precipitation. After filtering the reaction product, homogenization was performed using a mixed solution of acetone/water (volume ratio: 7:3), and after neutralization, washing was performed twice with acetone. The reaction product was vacuum dried at 50 degrees for 1 day to obtain 95 g of dextrin isostearate.

The yields of the dextrin esters prepared in Examples 1 to 5 are shown in Table 1 below.

dextrin
DE 11 acyl chloride
(input) reaction solvent reaction catalyst yield
(g) Example 1 17.8g palmitoyl chloride
(91g) N-ethyl-2-pyrrolidone 3-picoline 90g Example 2 17.8g palmitoyl chloride
(91g) N-ethyl-2-pyrrolidone pyridine 89g Example 3 17.8g Palmitoylchloride/Ethylhexylchloride
(75g/17g) N-ethyl-2-pyrrolidone 3-picoline 85g Example 4 17.8g Palmitoylchloride/Ethylhexylchloride
(75g/17g) N-ethyl-2-pyrrolidone pyridine 85g Example 5 17.8g Isostearoyl chloride (99g) N-ethyl-2-pyrrolidone 3-picoline 95g

Comparative Example 1. Preparation of Dextrin Palmitate

Using a 500 mL separate reactor equipped with a stirrer, thermometer and cooling tube, 30.7 g of N-methyl-2-pyrrolidone as a reaction solvent, 55 g of 3-picoline as a catalyst, and 17.8 g of dextrin as a starting material g (DE = 11, number average molecular weight = 1700, average degree of polymerization (n) = 10) was added, and the temperature was raised to 60 ° C. to dissolve completely. Thereafter, 40 g of 3-picoline was separately added to the above reactor, and then 91 g of palmitoyl chloride prepared according to Preparation Example 1 was slowly added. After completion of the addition, the temperature was raised to 80 ° C. and reacted for 4 hours. Thereafter, after slowly cooling to 50 ° C, 270 g of methanol was added and cooled to 25 ° C to proceed with precipitation. After filtering the reaction product, homogenization was performed using a mixed solution of acetone/water (volume ratio: 7:3), and after neutralization, washing was performed twice with acetone. The reaction product was vacuum dried at 50° C. for 1 day to obtain 89 g of dextrin palmitate.

Comparative Example 2. Preparation of Dextrin Palmitate

30.7 g of N-methyl-2-pyrrolidone as a reaction solvent, 46.7 g of pyridine as a catalyst, and 17.8 g of dextrin as a starting material ( DE = 11, number average molecular weight = 1700, average degree of polymerization (n) = 10) was added, and the temperature was raised to 60 ° C. to completely dissolve. Thereafter, 33 g of pyridine was separately added to the above reactor, and then 91 g of palmitoyl chloride prepared according to Preparation Example 1 was slowly introduced. After completion of the addition, the temperature was raised to 80 ° C. and reacted for 4 hours. Thereafter, after slowly cooling to 50 ° C, 270 g of methanol was added and cooled to 25 ° C to proceed with precipitation. After filtering the reaction product, homogenization was performed using a mixed solution of acetone/water (volume ratio: 7:3), and after neutralization, washing was performed twice with acetone. The reaction product was vacuum dried at 50° C. for 1 day to obtain 89 g of dextrin palmitate.

Comparative Example 3. Preparation of Dextrin Palmitate

20 g of acetamide as a reaction solvent, 46.7 g of pyridine as a catalyst, and 17.8 g of dextrin as a starting material (DE=11, number average molecular weight= 1700, average degree of polymerization (n) = 10) was added, and the temperature was raised to 60° C. to dissolve completely. Thereafter, 33 g of pyridine was separately added to the above reactor, and then 91 g of palmitoyl chloride prepared according to Preparation Example 1 was slowly introduced. After completion of the addition, the temperature was raised to 80 ° C. and reacted for 4 hours. Thereafter, after slowly cooling to 50 ° C, 270 g of methanol was added and cooled to 25 ° C to proceed with precipitation. After filtering the reaction product, homogenization was performed using a mixed solution of acetone/water (volume ratio: 7:3), and after neutralization, washing was performed twice with acetone. The reaction product was vacuum dried at 50° C. for 1 day to obtain 85 g of dextrin palmitate.

Comparative Example 4. Preparation of Dextrin Palmitate/Ethyl Hexanoate (Ratio of 27:10)

Using a 500 ml separate reactor equipped with a stirrer, thermometer and cooling tube, 30.7 g of N-methyl-2-pyrrolidone as a reaction solvent, 55 g of 3-picoline as a catalyst, and 17.8 g of dextrin as a starting material g (DE = 11, number average molecular weight = 1700, average degree of polymerization (n) = 10) was added and the temperature was raised to 60 ° C to completely dissolve. Thereafter, 40 g of 3-picoline was separately added to the above reactor, and then 75 g of palmitoyl chloride prepared according to Preparation Example 1 and 17 g of ethylhexanoyl chloride prepared according to Preparation Example 2 were slowly added. put in After completion of the addition, the temperature was raised to 80 ° C. and reacted for 4 hours. Thereafter, after slowly cooling to 50 ° C, 270 g of methanol was added and cooled to 25 ° C to proceed with precipitation. After filtering the reaction product, homogenization was performed using a mixture of acetone/water 7:3 (volume ratio: 7:3), neutralization was performed, and washing was performed twice with acetone. The reaction product was vacuum dried at 50° C. for one day to obtain 85 g of dextrin palmitate/ethyl hexanoate.

The yields of the dextrin esters prepared in Comparative Examples 1 to 4 are shown in Table 2 below.

dextrin
DE 11 acyl chloride
(input) reaction solvent reaction catalyst yield
(g) Comparative Example 1 17.8g palmitoyl chloride
(91g) N-methyl-2-pyrrolidone 3-picoline 89g Comparative Example 2 17.8g palmitoyl chloride
(91g) N-methyl-2-pyrrolidone pyridine 89g Comparative Example 3 17.8g palmitoyl chloride
(91g) acetamide pyridine 85g Comparative Example 4 17.8g Palmitoylchloride/
Ethylhexyl chloride
(75g/17g) N-methyl-2-pyrrolidone 3-picoline 85g

Experimental example

Experimental Example 1. Turbidity measurement

measurement method

The turbidity measurement method is to make a gel by adding 2 g of the dextrin esters according to Examples 1 to 5 and Comparative Examples 1 to 4 to 20 g of each emollient oil, and then measure the scattering degree by turbid particles. Nephelometry The Nephelometry Turbidity Unit (NTU) was measured, and the emollient oils used were mineral oil, isododecane, CEH (cetylethylhexanoate), MCT (medium chain triglyceride oil) and HUD (heptylundecylenate). At this time, the transparency of the components of the emollient oil for the reaction solvent used in the synthesis is shown in Table 3 below.

used for synthesis
reaction solvent Transparency (NTU) mineral oil isododecane CEH MCTs HUD N-ethyl-2-pyrrolidone 124 210 555 302 510 N-methyl-2-pyrrolidone 180 325 820 462 757

result

Referring to Table 4 below, in the case of dextrin esters according to Examples 1 to 5 prepared using N-ethyl-2-pyrrolidone as a reaction solvent, oil gels were prepared compared to dextrin esters according to Comparative Examples 1 to 4 It was confirmed that the transparency (NTU) of the city oil was improved.

division transparency
(NTU) division transparency
(NTU) Example 1 124 Comparative Example 1 180 Example 2 120 Comparative Example 2 165 Example 3 55 Comparative Example 3 350 Example 4 63 Comparative Example 4 95 Example 5 19

In addition, Table 5 below summarizes the hazard information of reaction solvents and reaction catalysts based on the "Act on Registration and Evaluation of Chemical Substances" and "Chemicals Control Act" of the Republic of Korea. It is characterized by combining selected substances by excluding harmful substances or toxic substances.

Referring to Table 5 below, when N-ethyl-2-pyrrolidone and acetamide are used as reaction solvents, and pyridine and 3-picoline are used as reaction catalysts, hazardous chemicals and critically controlled substances are not only excluded, but also However, even if a small amount of reaction solvent or reaction catalyst remains, concerns about hazards can be reduced.

However, in the case of dextrin palmitate of Comparative Example 3 in which acetamide as a reaction solvent and pyridine as a reaction catalyst were applied, it was confirmed that the transparency was relatively poor. It can be seen that

Therefore, when preparing the dextrin ester according to the present invention, N-ethyl-2-pyrrolidone is used as a reaction solvent and pyridine or 3-picoline is used as a reaction catalyst, thereby producing a dextrin ester having excellent physical properties. there is

hazardous chemicals Substances under priority control division reaction solvent N-methyl-2-pyrrolidone O O More than 0.3% toxic substances N-ethyl-2-pyrrolidone X X X Dimethylformamide O O More than 0.1% toxic substances acetamide X X X benzene O O More than 85% toxic substances toluene O O More than 85% toxic substances xylene O O More than 85% toxic substances reaction catalyst pyridine X X X 3-picoline X X X

Claims (8)

Method for preparing dextrin ester represented by Chemical Formula 1 by reacting dextrin with an acyl chloride represented by Chemical Formula 2 in the presence of N-ethyl-2-pyrrolidone as a reaction solvent:
[Formula 1]

[Formula 2]

In Formula 1,
A is hydrogen or (C=O)-R';
In this case, R' is a substituted or unsubstituted straight-chain or branched alkyl group having 3 to 25 carbon atoms,
n is an integer from 1 to 20;
In Formula 2,
R is a straight-chain or branched alkyl group having 3 to 25 carbon atoms. According to claim 1,
A method wherein the reaction is carried out in the presence of a catalyst. According to claim 2,
The method, characterized in that the catalyst is any one of 3-picoline or pyridine. According to claim 1,
In Formula 1,
A is hydrogen or (C=O)-R';
In this case, R' is a substituted or unsubstituted straight-chain or branched alkyl group having 7 to 21 carbon atoms,
wherein n is an integer from 1 to 12. According to claim 1,
In Formula 2,
R is a substituted or unsubstituted straight-chain or branched alkyl group having 7 to 21 carbon atoms. According to claim 1,
A method characterized in that the acyl chloride represented by Chemical Formula 2 is at least one of the compounds represented by Chemical Formulas 2-1 to 2-6:
[Formula 2-1]

[Formula 2-2]

[Formula 2-3]

[Formula 2-4]

[Formula 2-5]

[Formula 2-6]

In the compound represented by Formula 2-5, p and q are each independently an integer of 0 to 13, and the sum of p and q is 13. According to claim 1,
The dextrin ester represented by Formula 1 is dextrin laurate, dextrin myristate, dextrin palmitate, dextrin behenate, dextrin palmitate/ethylhexanoate ( Dextrin Palmitate / Ethyl Hexanoate) and dextrin isostearate (Dextrin Isostearate) method of any one selected from the group consisting of. According to claim 1,
A method characterized by reacting the dextrin and an acyl chloride represented by Formula 2 at a weight ratio of 1: 2.9 to 5.8.