KR20190105289A - Bio polymer and fabricating method of the same - Google Patents

Abstract

The present invention relates to a biopolymer compound synthesized by using a material derived from nature and a manufacturing method thereof. A polymer compound derived from nature according to an embodiment of the present invention is synthesized by using a cashew nut shell liquid (CNSL) as a starting material. A biopolyurethane manufactured by applying the biopolymer compound has improved thermal stability and mechanical properties.

Description

Naturally Derived Polymeric Compounds and Method for Preparing the Same {Bio polymer and fabricating method of the same}

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a biopolymer compound synthesized using a naturally derived material and a method for preparing the same, and to a polymer compound and a method for preparing the same, using as cashew net shell liquild (CNSL) a starting material.

Polyurethane is produced through a urethane reaction using a polyol compound having a hydroxyl group (-OH) and an isocyanate compound having an isocyanate group (-NCO) as raw materials. Until recently, the polyurethane industry used polyols obtained from petrochemical products as raw materials, but waste cooking oil, Daewoo oil, palm oil, linseed oil, rapeseed oil, etc. have increased as environmental awareness and demand for reproducible biopolyol have increased steadily. There is a growing interest in the development of multi-use eco-friendly polyol materials. In general, petroleum-based polyols have the advantages of low viscosity and excellent workability of the polyurethane produced, whereas biopolyols prepared from natural fats and oils have lower usability and physical properties of the prepared polyurethanes compared to petroleum-based polyols. It is known to have this low problem. Despite these problems, the development of the use of biopolyol is steadily progressing, and efforts to offset the shortcomings of the biopolyol through technology development of additives and the like continue.

Biopolyol production methods can be roughly classified into biological synthesis methods and chemical synthesis methods. Large companies such as Cargill, Dupont, and AMD manufacture and sell biopolyols in a biological manner using vegetable oils, but there is a problem that mass production is not easy due to the characteristics of biological methods. Thus, organic synthesis is preferred over biological synthesis.

Published Patent Publication No. 10-2009-0038269

The problem to be solved by the present invention relates to the production of non-edible bio-derived cardanol-based bio-polyols and bio-polyurethanes, to produce a bio-polyol by modifying the raw material cardanol, using the prepared bio-polyol To prepare polyurethane. The bio-polyurethanes produced in this way have antimicrobial properties and the possibility of improving physical properties. Therefore, cardanol-based biopolyols are not only substitutes for petroleum-based polyols, but also eco-friendly biopolyols as antimicrobial polyols with differentiated molecular structures. New possibilities for urethane production.

Other objects and advantages of the present invention will become apparent from the following detailed description, claims and drawings.

Naturally derived polyol compound according to an embodiment of the present invention for achieving the problem to be solved by using a cashew nut shell extract (cashew net shell liquild: CNSL) as a starting material.

The extract is any one of cardanol, cardol, methyl cardol, and anacardic acid.

When the extract is cardanol, it is represented by the following formula (2).

[Formula 2]

Naturally-derived polymer compound according to another embodiment of the present invention for achieving the problem to be solved by using a cashew nut shell extract (cashew net shell liquild: CNSL) as a starting material.

The extract is any one of cardanol, cardol, methyl cardol, and anacardic acid.

When the extract is the cardanol, it is represented by the following formula (2).

[Formula 2]

Naturally derived polymer compounds are represented by the following formula (3).

[Formula 3]

According to another aspect of the present invention, there is provided a method of preparing a polymer compound, wherein a cashew net shell liquild (CNSL) is used as a starting material, and the polyol compound is modified by modifying the extract. And preparing a polymer using the polyol compound.

The extract is any one of cardanol, cardol, methyl cardol, and anacardic acid.

When the extract is cardanol, preparing the polyol compound may include modifying the cardanol.

The modifying the cardanol may include reacting the cardanol with 1,4-dibromobutane and potassium carbonate to form an intermediate compound.

The method may further include preparing the polyol compound represented by Chemical Formula 2 by reacting the intermediate compound with potassium carbonate and diethanolamine.

[Formula 2]

When the polyol compound is a compound represented by the following Chemical Formula 2, the step of synthesizing the polymer may include reacting the compound represented by the following Chemical Formula 2 and the following Chemical Formula 4.

[Formula 2]

[Formula 4]

When the polymer is synthesized, the compound of Formula 4 and the compound of Formula 2 are reacted such that the ratio (-NCO / -OH) of the -NCO group of Formula 4 to the -OH group of Formula 2 is 1.1 to 1.4.

The polymer is represented by the following formula (3).

[Formula 3]

According to the present invention, a biopolyol compound of a petroleum substitute can be applied by producing a biopolyol compound using cardanol which is a non-edible bio-derived material. In addition, the conventional vegetable oil bio polyol compound has the disadvantages of hydrolysis and degradation to microorganisms, the present invention overcomes these disadvantages, the bio-polyurethane prepared by applying it has improved thermal stability and mechanical properties. In addition, since the bio-polyurethane according to the present invention can be thermally cured, it also has an improvement in physical properties due to heat.

1 is a flow chart showing a method for producing a polymer compound according to an embodiment of the present invention.
Figure 2 shows the functional group NMR peak of the molecular structure before and after the synthesis of the polyol.
Figure 3 shows the IR measurement results of the molecular bonds before and after the synthesis of the polyol.
Figure 4 is a photograph of the polyurethane film produced by the present invention.
Figure 5 shows the results of IR measurement of molecular bonds before and after the synthesis of polyurethane.
Figure 6 is a photograph experimenting with the antimicrobial properties of the polyurethane film.
Figure 7 shows the degree of curing reaction of polyurethane with heat and reaction time.
8 is a TGA measurement result for the polyurethane of the present invention.
Figure 9 compares the tensile strength of the polyurethane and polyurethane film.

Advantages and features of the present invention and methods for achieving them will be apparent with reference to the embodiments described below in detail with the accompanying drawings. However, the present invention is not limited to the embodiments disclosed below, but will be implemented in various forms, and only the present embodiments are intended to complete the disclosure of the present invention, and the general knowledge in the art to which the present invention pertains. It is provided to fully convey the scope of the invention to those skilled in the art, and the present invention is defined only by the scope of the claims. DETAILED DESCRIPTION Hereinafter, exemplary embodiments of the present invention will be described in detail with reference to the accompanying drawings. Regardless of the drawings, the same reference numbers refer to the same components, and “and / or” includes each and every combination of one or more of the items mentioned.

The terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention. In this specification, the singular also includes the plural unless specifically stated otherwise in the phrase. As used herein, "comprises" and / or "comprising" does not exclude the presence or addition of one or more other components in addition to the mentioned components.

Unless otherwise defined, all terms (including technical and scientific terms) used in the present specification may be used in a sense that can be commonly understood by those skilled in the art. In addition, the terms defined in the commonly used dictionaries are not ideally or excessively interpreted unless they are specifically defined clearly.

Hereinafter, a naturally derived polyol compound and a naturally derived polymer compound based on the same will be described.

Naturally derived polyol compounds and polymer compounds of the present invention are each a cashew net shell liquild (CNSL) as a starting material.

Derivatives derived from the cashew nut shell extract, a natural vegetable oil extracted from the cashew fruit skin of the lacquer family in the rain forest, have been widely used in epoxy curing agents, phenolic resins, surfactants and emulsion breakers. Such cashew nut shell extracts include cardanol, kadol, methyl kadol, anacardic acid, and the like. Naturally derived polyol compounds and polymer compounds according to an embodiment of the present invention can be prepared using any one of the extracts listed above as a starting material. However, in consideration of processability or antimicrobial activity, it is most preferable to select cardanol as a starting material. Hereinafter, for convenience of explanation, it is assumed that the cashew nut shell extract is cardanol.

Cardanol is a substance represented by the following formula (1).

[Formula 1]

As can be seen from the above formula, cardanol is a mixture of phenol derivatives having four kinds of alkyl groups in the meta position, and compounds having respective alkyl groups are 3%, 34%, 22% and 41%, respectively, as described above. It is mixed at the ratio of.

However, cardanol itself has a problem that the stability is not great. In addition, phenolic groups present in cardanol are known to corrode skin mucosa, denature proteins and cell prototypes, damage cell membranes of erythrocytes and interfere with the transfer of oxygen to cause cancer. In addition, since the polymerization reactivity is very low, only a polymer having a number average molecular weight of several thousand or less can be obtained even if polymerization and curing are caused by oxidation by maintaining an appropriate temperature and humidity.

Thus, in order to use cardanol in the synthesis of high molecular materials, modification is required.

Using cardanol as a starting material, it is possible to form a polyol compound which is an intermediate for polymer synthesis.

Naturally-derived polyol compounds prepared using cardanol, a component derived from consulates, may be represented by the following formula (2).

[Formula 2]

Based on the cardanol, the preparation of the polyol compound will be described later. On the other hand, the polyol compound, of course, in addition to the above-described cardanol, may be formed by using the starting material, kadol, methyl kadol, anacardic acid as the cashew nut shell extract.

On the other hand, the polymer compound according to an embodiment of the present invention can be synthesized as a cashew nut shell extract which is a natural component. That is, the polymer compound may be synthesized with any one of the cashew nut shell extract cardanol, kadol, methyl kadol, and anacardic acid. Preferably cardanol may be used.

When synthesizing a naturally-derived high molecular compound by using a cardanol as a starting material, the above-described polyol compound of Formula 2 may be used as an intermediate material. That is, based on the polyol compound of Formula 2, it is possible to synthesize a natural-derived polymer compound. Based on the cardanol as a starting material, based on the polyol compound of Formula 2, the synthesized natural-derived polymer compound may be represented by the following formula (3).

[Formula 3]

Subsequently, a description will be given of a method for producing a naturally-derived polymer compound according to another embodiment of the present invention.

1 is a flow chart showing a method for producing a naturally-derived polymer compound according to an embodiment of the present invention.

Referring to FIG. 1, in the method for preparing a natural-derived polymer compound according to an embodiment of the present invention, a cashew net shell liquild (CNSL) is used as a starting material, and the extract is modified (S10). It may include preparing a polyol compound (S20), and synthesizing a polymer using the polyol compound (S30).

First, cashew nut shell extract (cashew net shell liquild: CNSL) is modified (S10). The cashew nut shell extract may be selected from cardanol, cardol, methyl cardol, and anacardic acid. However, cardanol may be preferably selected. Hereinafter, for convenience of explanation, it is assumed that the extract is cardanol.

Cardanol is a substance represented by the following formula (1).

[Formula 1]

As can be seen from the above formula, cardanol is a mixture of phenol derivatives having four kinds of alkyl groups in the meta position, and compounds having respective alkyl groups are 3%, 34%, 22% and 41%, respectively, as described above. It is mixed at the ratio of.

Since cardanol is inferior in processability by itself, it is common to modify and use cardanol. According to an embodiment of the present invention, cardanol may be modified in two stages.

The first step of modifying cardanol is the reaction of cardanol with 1,4-dibromobutane and potassium carbonate to form an intermediate compound. In this case, the cardanol and 1, 4-dibromobutane and potassium carbonate may be dispersed in a solvent to proceed with the reaction. For example, acetone may be used as the solvent, but is not limited thereto. The one stage reforming reaction can be carried out, for example, at reflux for 24 hours. If necessary during the reaction, precipitation and unreacted material removal processes may be further performed to increase the purity of the intermediate compound.

Subsequently, the second step of modifying cardanol is to react the intermediate compound with potassium carbonate and diethanolamine. In this case, the intermediate compound, potassium carbonate and diethanolamine may be dispersed in a solvent to proceed with the reaction. For example, tetrahydrofuran may be used as the solvent, but is not limited thereto. After the reaction, after removing the solvent to be loaded, fractional extraction may be performed using ethyl acetate and distilled water. After fractionation, a final reformate of cardanol dissolved in ethyl acetate is obtained. Through this process, a polyol compound represented by Chemical Formula 2 is prepared. That is, the cardanol, which is a natural component, is finally modified into a polyol compound represented by Chemical Formula 2 through a two-stage reforming reaction.

[Formula 2]

Next, a polymer is synthesized using the polyol compound represented by Chemical Formula 2 (S30).

Synthesis of the polymer is carried out by reacting the polyol compound represented by Formula 2 with the polyfunctional isocyanate compound represented by Formula 4.

[Formula 4]

A polyurethane polymer compound represented by the following Chemical Formula 3 may be synthesized through a urethane reaction between a hydroxyl group (-OH) of Formula 2 and an isocyanate group (-NCO) of Formula 4.

[Formula 3]

In this case, the compound of Formula 4 and the compound of Formula 2 may be reacted such that the ratio (-NCO / -OH) of the -NCO group of Formula 4 to the -OH group of Formula 2 is 1.1 to 1.4. When the ratio is less than 1.1, the mechanical strength is weak, so that the free standing can not be a high molecular compound, when the ratio exceeds 1.4, the mechanical strength can be secured (that is, the polymer is free standing) can be mixed The economy cannot be satisfactory.

Synthesis process of the polymer compound according to an embodiment of the present invention can be represented as follows.

By reacting the polyol compound of formula (2) and the polyfunctional isocyanate compound represented by formula (4), a polyurethane polymer compound represented by the formula (3) is finally synthesized. In another embodiment of the present invention, the polymer compound may include a natural component, thereby replacing the petroleum component.

The biopolyol compound of a petroleum substitute can be applied by manufacturing the bio polyol compound using cardanol which is a non-edible bio-derived substance. In addition, the conventional vegetable oil bio polyol compound had the disadvantages of hydrolysis and degradation to microorganisms, the present invention overcomes these disadvantages, the bio-polyurethane prepared by applying this showed improved thermal stability and mechanical properties. In addition, since the bio-polyurethane according to the present invention can be thermally cured, it was also expected to improve physical properties due to heat.

Therefore, biopolyurethanes using such cardanol-based biopolyols are basically functional biopolyurethanes because they possess antibacterial properties, and can be biopolyurethanes having improved physical properties (mechanical and thermal).

Hereinafter, the present invention will be described in more detail with reference to Examples. These examples are only for illustrating the present invention in more detail, it will be apparent to those skilled in the art that the scope of the present invention is not limited by these examples in accordance with the gist of the present invention. .

Preparation Example 1 Synthesis of Polyol Compound

After dissolving cardanol (0.02 mol, 6 g, Palmer, USA), 1,4 dibromobutane (0.02 mol, 3 g, Sigma, USA) and potassium carbonate (0.02 mol, 3 g, Sigma, USA) in an acetone solvent, The reaction was carried out. The reaction was carried out at reflux for 24 hours, and precipitated using methanol to remove unreacted material after completion of the reaction. After several precipitations, all remaining solvent was removed to obtain an intermediate compound.

Subsequently, the obtained intermediate compound (0.02 mol, 3 g), potassium carbonate (0.02 mol, 3 g) and diethanolamine (0.02 mol, 3 g, Sigma, USA) were dissolved in tetrahydrofuran (THF) solvent for 24 hours. The reaction was carried out at reflux. After removing the remaining solvent after the reaction first, the separation was performed using ethyl acetate (EA) and distilled water. Then, the remaining solvent was removed to take the modified cardanol dissolved in EA to obtain a polyol compound that is a modified cardanol.

Figure 2 shows the functional group NMR peak of the molecular structure before and after the synthesis of the polyol, Figure 3 shows the IR measurement results of the molecular bonds before and after the synthesis of the polyol. As can be seen in Figures 2 and 3, it can be seen that the peak for -OH appeared while maintaining the basic skeleton of cardanol. That is, it can be seen that by the preparation example, a cardanol-based polyol compound was prepared.

Preparation Example 2 Polyurethane Polymer Synthesis

A polyol compound (0.02 mol, 3 g) prepared in Preparation Example 1 and a polyfunctional isocyanate compound (0.026 mol, 3.9 g, Sigma, USA) represented by the following Chemical Formula 4 of Chemical Formula 4 were dissolved in tetrahydrofuran (THF) as a solvent. It dissolved and proceeded the polymer synthesis reaction.

[Formula 4]

After reacting in the reactor, the stirring solution was cast on a 140 mm × 140 mm (length × width) Teflon mold. Curing at 50 ° C. for 24 hours after casting. Thereafter, residual solvent present in the film was removed in a vacuum oven at 50 ° C. for 24 hours. Thereby, the polyurethane film like FIG. 4 was manufactured. Formula 5 shows a crosslinked polyurethane film.

[Formula 5]

Figure 5 shows the results of IR measurement of molecular bonds before and after the synthesis of polyurethane. As can be seen in Figure 5, it can be seen that the urethane functional group appeared after the reaction while maintaining the basic skeleton of the polyol. That is, it can be seen that the polyurethane based on the polyol compound of Preparation Example 1 was prepared by the Preparation Example.

Experimental Example 1: Determination of the antimicrobial activity of the prepared polyurethane

Escherichia coli (E. coli, ATCC 8739) was investigated the antimicrobial activity of the polyurethane film prepared using the shaking flask method. E. coli cells were incubated in nutrient solution for 18 hours at 37 ° C. to prepare bacterial suspensions. The colonies were used to lift the colonies in 30mL nutrient medium and incubated with shaking at 37 ° C for 18 hours. After washing twice with Phosphate buffersaline (PBS) solution, redispersed in PBS solution to yield 1 × 10 ⁷ CFU (colony-forming unit) per mL. The bacterial cell concentration was estimated by measuring the absorbance of the cell dispersion at 600 nm by comparison with the standard calibration curve. In order to evaluate the bactericidal activity of the polyurethane film, the film was immersed in a bacterial suspension (2 cm × 2 cm) and shaken at 25 ° C. for 24 hours. The solution was then serially diluted and 0.1 mL of 1 × 10 ⁴ CFU dilution was spread over agar medium. Spreaded agar medium was incubated at 37 ° C. for 18 hours, and the number of surviving colonies was counted. Antimicrobial activity was calculated through the following equation (1).

Expression (1): Bactericidal property (%) = 100x (N ₀ -N _i ) / N ₀

N ₀ : bacterial CFU of blank

N _i : bacterial CFU of tested sample

The prepared bio polyurethane showed a bacteriostatic reduction rate of 99.9% when compared to the blank solution. That is, it was found that the polyurethane of the present invention has excellent antibacterial properties. FIG. 6 is a photograph of the antimicrobial activity of the polyurethane film. Referring to FIG. 6, it was confirmed that the polyurethane of the present invention had antimicrobial activity.

Experimental Example 2 Measurement of the Curing Reaction of the Prepared Polyurethane Film

The double bond in the polyol compound is a heat-curable part, and the polyurethane film manufactured based on this may be heat-cured at a condition of 120 to 160 ° C. This was measured experimentally. Attempt to heat the polyurethane for 7 days at 150 ℃ conditions did not proceed curing (a of Figure 7). When cobalt naphthenate was added 3wt% when preparing a polyurethane film as an accelerator to assist the curing progress, it was confirmed that the thermal curing is performed under the same conditions for 48 hours (Fig. 7b). Figure 7 shows the degree of curing reaction of polyurethane with heat and reaction time.

Experimental Example 3: Measurement of physical properties according to before and after curing of the prepared polyurethane

(1) thermal stability analysis (TGA)

Thermal stability characteristics were measured through the change in thermal weight of the sample. Experiments were performed using a TGA 4000 from Perkinelmer to measure the change in thermal weight.

In the case of vegetable oil, the thermal stability is low, but cardanol, which is a raw material of the polyurethane of the present invention, is basically higher in thermal stability than vegetable oil. Therefore, the polyol synthesized on the cardanol basis is expected to have excellent thermal stability, and the polyurethane film synthesized on the basis of the polyol is also expected to have excellent thermal stability. Experiments were conducted to verify the predictions and, as predicted, the polyurethanes of the present invention were found to have excellent thermal stability.

In addition, it was proved by experiment that the progress to the curing reaction showed a more improved thermal stability as compared to the existing thermal stability as a whole. 8 is a TGA measurement result for the polyurethane of the present invention. Referring to FIG. 8, the polyurethane of the present invention showed improved thermal stability compared to cardanol, which is a raw material, and in particular, in the case of a cured polyurethane film (cross-linking BPU film), it was found that the thermal stability was remarkable. . In addition, these figures are summarized in Table 1 below.

Sample T _5% ^a (℃) T _5% ^a (℃) T _5% ^a (℃) Residual amount (%, 700 ℃) Cardanol 259.07 277.17 321.17 0.16 Polyol 303.33 318.5 363.67 2.52 Polyurethane 284.00 303.50 366.67 0.99 Curing polyurethane 312.67 336.33 461.17 16.89

(2) measuring mechanical properties

Mechanical properties were measured using a universal testing machine (QM100S, Qmesys, Korea), and the tensile strength was measured at room temperature with the cross-head speed of 50 mm / min. The size of the measuring film was all the same in the standard of 50mm x 15mm (length x width). Referring to FIG. 9, it can be seen that as the curing proceeds, the tensile strength is increased by about 3 times or more compared to the existing polyurethane. In addition, these figures are summarized in Table 2 below.

Sample Tensile strength (MPa) Elongation at break (%) Young's modulus (MPa) Polyurethane 2.013 ± 0.06 135.92 ± 4.75 14.96 ± 1.47 Curing polyurethane 6.787 ± 0.63 5.01 ± 0.47 127.09 ± 14.84

(3) absorbance measurement

Moisture absorption of polyurethane film is measured according to ASTM D570 by 166 hours of immersion for 20 mm x 20 mm (length x width) of film so as to reach equilibrium, and then remove moisture remaining on the surface of the film. It calculated using (2).

Equation (2):

W ₀ : the weight of the dry sample (g)

W ₁ : the weight of the wet sample (g)

The prepared film was cut into lengths of 10 mm in width and 10 mm in width, and the initial weight (W ₀ ) was measured. Then, the film was loaded in distilled water at room temperature to measure the weight (W ₁ ) at intervals of about 5 minutes. The results are summarized in Table 3 below.

Sample Gel content (%) Water uptake (%) 5 wt% H ₂ SO ₄ 5wt% NaOH 5wt% NaCl Polyurethane 65.93 ± 0.48 4.10 ± 0.47 Ⅱ Ⅲ Ⅲ Curing polyurethane 86.93 ± 0.88 3.70 ± 0.32 Ⅲ Ⅲ Ⅲ

(4) Crosslinking degree measurement

In order to evaluate the degree of crosslinking before and after crosslinking of the polyurethane film, the 20mmx20mm (lengthxwidth) film was immersed in the toluene solution for 166 hours to allow sufficient equilibrium to be reached. The oven was dried at 80 ° C. for about 2 hours and then the film weight change was measured. The average value was derived using a total of five samples, and the gel content was calculated through the equation (3). The results are summarized in Table 3 above.

Equation (3):

W _g : the weight of the insoluble sample (g)

W _f : the weight of the original sample (g)

(5) chemical resistance evaluation

Chemical resistance evaluation was observed for the change of the film after immersing the film for 166 hours in 5wt% H ₂ SO ₄ , 5wt% NaOH, 5wt% NaCl aqueous solution, respectively. The results are summarized in Table 3 above.

Referring to Table 3, it can be seen that the bio polyurethane has a high water resistance and chemical resistance regardless of the curing.

Although the embodiments of the present invention have been described above, the present invention is not limited to the above embodiments and can be manufactured in various forms, and a person of ordinary skill in the art to which the present invention pertains has the technical idea of the present invention. However, it will be understood that other specific forms may be practiced without changing the essential features. Therefore, it should be understood that the embodiments described above are exemplary in all respects and not restrictive.

Claims (15)

Naturally derived polyol compound derived from cashew net shell liquild (CNSL) as a starting material. The method of claim 1,
The extract is a natural polyol compound of any one of cardanol, kadol, methyl kadol, anacardic acid. The method of claim 1,
When the extract is cardanol, a naturally occurring polyol compound represented by the following formula (2).
[Formula 2]

Naturally derived high molecular compound synthesized using cashew net shell liquild (CNSL) as a starting material. The method of claim 4, wherein
The extract is any one of cardanol, kadol, methyl kadol, anacardic acid-derived natural polymer compound. The method of claim 4, wherein
When the extract is the cardanol, a natural derived polymer compound synthesized by a polyol compound represented by the following formula (2).
[Formula 2]

The method of claim 6,
Naturally derived high molecular compound represented by the formula (3).
[Formula 3]

In the production method of a naturally-derived high molecular compound using cashew net shell liquild (CNSL) as a starting material,
Modifying the extract to prepare a polyol compound; And
Method of producing a natural-derived polymer compound comprising the step of synthesizing a polymer using the polyol compound. The method of claim 8,
The extract is a method of producing a natural-derived polymer compound is any one of cardanol, kadol, methyl kadol, anacardic acid. The method of claim 8,
When the extract is cardanol, the step of preparing the polyol compound, a method of producing a natural-derived polymer compound comprising the step of modifying the cardanol. The method of claim 10,
The step of modifying the cardanol,
A method for producing a natural-derived polymer compound comprising the step of reacting the cardanol with 1,4-dibromobutane and potassium carbonate to form an intermediate compound. The method of claim 11,
A method for preparing a naturally-derived polymer compound further comprising the step of reacting the intermediate compound with potassium carbonate and diethanolamine to prepare the polyol compound represented by the following Chemical Formula 2.
[Formula 2]

The method of claim 8,
When the polyol compound is a compound represented by Formula 2, the step of synthesizing the polymer,
A method for preparing a naturally-derived polymer compound comprising reacting a compound represented by the following Chemical Formula 2 and the following Chemical Formula 4.
[Formula 2]

[Formula 4]

The method of claim 13,
When the polymer is synthesized, a natural derivative of reacting the compound of Formula 4 and the compound of Formula 2 so that the ratio (-NCO / -OH) of the -NCO group of Formula 4 to the -OH group of Formula 2 is 1.1 to 1.4 Method for producing a high molecular compound. The method of claim 13,
The polymer is a method of producing a natural-derived polymer compound represented by the formula (3).
[Formula 3]

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