KR100308535B1 - Polyester resin composition and method for producing the same - Google Patents

Abstract

PURPOSE: Provided is a polyester resin composition which has mechanical properties such as melt viscosity requisite for numerous cast processing for moldings and sufficient tear strength requisite for moldings, and a method for producing the same. CONSTITUTION: The polyester resin composition is prepared by the steps of (i) subjecting aliphatic(including cycloaliphatic) dicarboxylic acid(or its anhydride) comprising adipic acid and 0.1-50 wt.%(based on a theoretical weight of polyester) of monomers containing one or two and more hydroxyl group, amine group, and carboxylic group as a functional group to any one or two and more reactions selected from condensation, esterification, and transesterification reactions at 160-240deg.C, (ii) adding aliphatic(including cycloaliphatic) glycol comprising at least any one selected from 1,4-butane diol and ethylene glycol to product obtained from the (i) and subjecting them to esterification or transesterification reaction at 200-220deg.C, and (iii) polycondensing a product obtained from the (ii) at the temperature of 210-270deg.C and degree of vacuum of 0.005-10 torr to produce a high molecular polyester.

Description

[Name of invention]

Polyester resin composition and its manufacturing method

Detailed description of the invention

[Purpose of invention]

[Technical field to which the invention belongs and the prior art in that field]

The present invention relates to a polyester resin composition and a method for manufacturing the same, and in particular, the conventional aliphatic polyester has a biodegradability and solves the difficulty of practical use as a trash bag or shopping bag caused by the lack of tear strength. A high molecular weight polyester resin composition and a method for producing the same.

Representative polyester resins used in various applications such as fibers, molded articles and films are high molecular weight aromatic polyester resins produced by condensation polymerization of terephthalic acid and ethylene glycol or terephthalic acid and 1,4-butanediol, wherein high molecular weight poly Ester refers to a polymer having a number average molecular weight of 10,000 or more. However, the aromatic polyester resins do not decompose in the natural ecosystem after disposal and have remained for a long time causing serious environmental pollution problems.

On the other hand, it is already known that aliphatic polyesters are biodegradable (see Journal of Macromol. SCI-Chem., A-23 (3), 1986, 393-409), and are currently used for medical materials, agricultural and fishery materials, and Some applications have been made in packaging materials, and other practical researches have been carried out.

However, due to the flexible structure and low crystallinity of the main chain, the existing aliphatic polyester has low melting point and low thermal stability during melting, which is easy to thermally decompose, and it is not easy to form processing due to the melt flow index, as well as tensile strength and tearing steel. There is a problem that the use is limited because of poor physical properties such as. In order to put the aliphatic polyester into practical use, the number average molecular weight must be raised to 30,000 or more, but it is difficult to raise the number average molecular weight of the aliphatic polyester to 15,000 or more in a commonly known condensation polymerization system.

As one method for solving this problem, a method of synthesizing a high molecular weight aliphatic polyester resin having a number average molecular weight of 30,000 or more by appropriately adjusting the reaction temperature, vacuum degree and catalyst conditions is disclosed in Korean Patent Application Laid-Open No. 95-758. It is disclosed in the call. However, the aliphatic polyester resins produced by this method have a low weight average molecular weight, are extremely sensitive to heat, and have poor moldability.

As another conventional example, Korean Patent Laid-Open Publication No. 95-14171 discloses a method for producing a high molecular weight aliphatic polyester by adding a monomer of trivalent or higher polyhydric alcohol or trivalent or higher polyhydric carboxylic acid during polyester production. Is disclosed. According to this method, by introducing the monomer into the reaction system, the reaction time can be shortened, the molecular weight distribution can be diffused, and the moldability can be improved. However, since the low molecular weight polyester is rapidly increased to decrease the physical properties such as tensile strength, it is not only practical to use, but also has a problem of high gelation, which makes it difficult to control the reactivity.

Another method of raising the number average molecular weight of aliphatic polyester is disclosed in Korean Patent Application Laid-Open No. 95-25072, which refers to (1) aliphatic (including cyclic aliphatic) glycols, and (2) Presence or ratio of aliphatic (including cyclic aliphatic) dicarboxylic acids (or acid anhydrides) as a main component and a small amount of (3) trivalent or more polyhydric alcohols or trivalent or higher polyhydric carboxylic acid (or acid anhydrides) monomers The high molecular weight aliphatic polyester composition obtained by making the isocyanate which is a coupling agent react with the aliphatic polyester of the number average molecular weight 15,000-20,000 obtained by dehydration reaction and the deglycol reaction in presence is further disclosed. The number average molecular weight of the aliphatic polyester resin obtained by this method was about 20,000-70,000. However, according to this method, since the reaction time is long, productivity decreases, and the isocyanate which is a coupling agent used to increase the molecular weight is extremely harmful to the human body.

As described above, in order to prepare a high molecular weight aliphatic polyester resin, a method of adding isocyanate, which is a coupling agent, or a polyfunctional monomer such as polyhydric alcohol or polyhydric carboxylic acid is used in preparing the aliphatic polyester. come. However, the aliphatic polyester thus prepared had problems with productivity, physical properties, moldability, and the like.

[Technical problem to be achieved]

It is an object of the present invention to provide a biodegradable polyester resin composition having a high molecular weight sufficient for practical use and a method for producing the same.

Another object of the present invention is to provide a polyester resin composition having mechanical properties such as melt viscosity required for various molding processes such as injection molding, blow molding, film molding, and the like, and sufficient tear strength required for practical use of the molded article, and a manufacturing method thereof. It is.

[Configuration and Function of Invention]

According to the present invention, (1) an aliphatic (including cyclic aliphatic) dicarboxylic acid (or anhydride thereof) containing adipic acid, and (2) at least one selected from 1,4-butanediol and ethylene glycol In the presence of a monomer containing aliphatic (including cyclic aliphatic) glycol as a main component and each containing one or more hydroxyl groups, amine groups and carboxyl groups as functional groups of 0,1 to 30% by weight relative to the theoretical weight of polyester. Provided is a polyester resin composition obtained by subjecting one or two or more reactions selected from a condensation reaction, an esterification reaction, and a transesterification reaction to a polycondensation reaction.

In order to prevent the rapid increase and gelation of low molecular weight polyester during the preparation of the polyester resin, preferably, any one of condensation reaction, esterification reaction and transesterification reaction is performed by first adding the dicarboxylic acid and the monomer. After distilling out water or methanol, the resulting reaction product and the glycol are esterified or transesterified, followed by polycondensation reaction of the reaction product to produce a high molecular weight polyester resin. It is characterized by.

The polyester resin composition of the present invention will be described in more detail. An aliphatic (including cyclic aliphatic) dicarboxylic acid (or anhydride thereof) containing adipic acid as a main component, 1,4-butanediol and ethylene glycol Aliphatic (including cyclic aliphatic) glycols containing any one or more selected from the group consisting of: adipic acid monocomponent and 1,4-butanediol monocomponent; ② adipic acid monocomponent and ethylene glycol monocomponent ③ adipic acid monocomponent, 1,4-butanediol and other glycols (glycols having alkylene groups (including cyclic alkylene groups) having 2 to 3 and 5 to 10 carbon atoms) Mixed components of; ④ Using any one selected from adipic acid and other dicarboxylic acids (dicarboxylic acid having 2 to 3 and 5 to 10 alkylene groups (including cyclic alkylene groups) and 1,4-butanediol) do. In this case, in the case of ③, the ratio of 1,4-butanediol and other glycols is 85:15 to 100: 0, and in case of ④, the ratio of adipic acid and other dicarboxylic acids is 90:10 to 100. It is characterized by: 0.

As the monomer added to the present invention, a monomer containing one or two or more hydroxyl groups, amine groups and carboxyl groups may be used as a functional group. Examples thereof include 3-amino-4-hydroxybenzoic acid and 4-amino-3-hydroxybenzoic. acid, 2-amino-5-hydroxybenzoic acid, aminosalicylic acid, 3-chloro-L-tyrosine, L-3- (3,4-dihydroxyphenyl) alanine, and the like, and any one or a mixture of two or more thereof selected from the present invention It is used as a monomer of.

In addition, according to the present invention is provided a method for producing the aliphatic polyester resin, the production method is composed of a three-step reaction, will be described below divided by step.

In the first stage reaction for producing the polyester resin of the present invention, an aliphatic (including cyclic aliphatic) dicarboxylic acid (or anhydride thereof) containing adipic acid and a hydroxyl group, an amine group, and a carboxyl group are each one as a functional group. Alternatively, by adding a monomer containing two or more, water or methanol produced by condensation reaction, esterification reaction, and transesterification reaction at a temperature of 160-240 ° C. or two or more reactions is discharged. At this time, if the reaction temperature is less than 160 ℃ water or methanol is difficult to escape, whereas if it exceeds 240 ℃, the reaction products may be carbonized or scattered, so pay attention to the reaction temperature control. In addition, the addition amount of the monomer is preferably about 0.1 to 30% by weight relative to the theoretical weight of the polyester, if the addition amount is less than 0.1% by weight not only the reaction time is long, but also the physical properties are lowered, while the addition amount is 30% by weight Beyond this, the rate of biodegradation is delayed and the melting point is too high, causing problems in the molding process and increasing costs. The chemical reaction proceeding in this process is shown in Scheme 1 below, wherein the dicarboxylic acid is adipic acid, and the monomer is 4-amino-3-hydride containing one amine group, one hydroxyl group and one carboxyl group. An example using oxybenzoic acid is shown.

However, in Reaction Formula 1, n is 1 to 50 as an integer. Since the dicarboxylic acid component is more added than the monomer component, the dicarboxylic acid is bonded to the sock end of the reaction product, and the reaction produces a reaction product having a number average molecular weight of 200 to 10,000. Thereafter, the unreacted dicarboxylic acid component remains in the reaction system.

Next, in the second stage reaction, aliphatic (including cyclic aliphatic) glycol containing any one or more selected from 1,4-butanediol and ethylene glycol is added to the first stage reaction product at a temperature of 200 to 220 ° C. The esterification reaction or the transesterification reaction is carried out to completely discharge the water or methanol produced. The chemical reaction proceeding in this process is shown in the following schemes 2 and 3, wherein the glycol is shown an example using 1,4-butanediol. In addition, Scheme 2 below shows a chemical reaction between the reaction product of Scheme 1 and aliphatic (including cyclic aliphatic) glycol, and Scheme 3 shows unreacted aliphatic (including cyclic aliphatic) remaining in the reaction system of the first stage reaction. The esterification reaction of a carboxylic acid (or anhydride thereof) with an aliphatic (including cyclic aliphatic) glycol is shown.

Reaction Schemes 2 and 3 show only representative examples of chemical reactions that proceed in the reaction system, n is 1 to 50 as an integer as in Scheme 1, and m is 180 to 400 as an integer.

At this time, the reaction molar ratio of the glycol and the dicarboxylic acid introduced in the first step ranges from 1: 1.1 to 1: 2. When the molar ratio is less than 1: 1.1, the reactivity decreases and affects color. On the other hand, exceeding 1: 2 is expensive. Therefore, it is preferable that the molar ratio of the said compound is 1: 1.4.

Finally, in the third step reaction, the polyester, which is the second step reaction product, is polycondensed for 60 to 200 minutes at a temperature of 210 to 270 ° C. and a vacuum of 0.005 to 10 torr to produce a high molecular weight polyester. That is, after the reaction product and the unreacted dicarboxylic acid component generated in the first step described above have undergone chemical reactions as in Scheme 2 and Scheme 3, respectively, they are continuously discharged with water, methanol, or glycol. Reaction with adjacent molecules forms a polyester resin having a number average molecular weight of 30,000 to 70,000 and a weight average molecular weight of 160,000 to 600,000.

Meanwhile, according to the present invention, a catalyst may be added at the beginning or the end of the second stage esterification reaction or transesterification reaction, the addition amount of which is 0.02% by weight to 2% by weight relative to the total composition weight. When the addition amount is less than 0.02% by weight, it is difficult to pour out the theoretical amount of water, methanol or glycol, and it takes a considerable time to pour out the theoretical amount of the water, methanol or glycol, while when the addition amount of the catalyst exceeds 2% by weight The theoretical amount of water, methanol or glycol is easily spilled but can affect color. At this time, any catalyst selected from metal compounds containing Ti, Ge, Zu, Fe, Mu ₂ , Co, Zr and the like is used as the catalyst to be used, and preferably titanate, antimonate, An organometallic compound containing tin oxide is used, more preferably in tetrabutyl titanate, calcium acetate, antimony oxide, dibutyl tin oxide, zinc acetate, antimonia acetate, antimony glycolate, tetrapropyl titanate Any one or two or more mixed catalysts selected are used.

In addition, the stabilizer may be added at the beginning or the end of the second stage esterification reaction or transesterification reaction, the addition amount is 0.02% to 2% by weight of the total composition. If the added amount is less than 0.02% by weight, the effect as a stabilizer is not obtained, the color becomes worse, whereas if the added amount of the stabilizer exceeds 2% by weight, the reaction rate becomes long and it is difficult to obtain a high molecular weight polyester. Therefore, the addition amount of the stabilizer is preferably 0.22% by weight, and any one or two or more mixed stabilizers selected from phosphate-based stabilizers such as trimethyl phosphate, phospheric acid, triphenyl phosphate and the like are used as the stabilizer.

In other words, the polyester resin of the present invention is a high molecular weight polymer through a three-step reaction, the number average molecular weight of the polyester resin is 30,000 ~ 70,000, the weight average molecular weight is 160,000 ~ 600,000, the melting point is 45 ~ 60 ℃, and the melt index is 0.1 ~ 50 (190 ℃, 2160g).

In addition, since the polyester resin according to the present invention has excellent tear strength, it is possible to solve the limitation on practical use that has occurred due to the lack of tear strength in the past. For example, it is difficult to manufacture and use a garbage bag and a shopping bag with an existing aliphatic polyester resin, so it is difficult to tear, but the polyester according to the present invention has improved tearing strength by an amine group present in a molecule, thereby enabling practical use. .

Hereinafter, the present invention will be described in more detail using examples.

Example 1

The 500 ml Erlenmeyer flask was replaced with nitrogen, and then 146 g of adipic acid and 4 g of 4-amino-3-hydroxybenzoic acid were added, followed by esterification while gradually raising the temperature to allow water to flow out. At this time, after fixing at a temperature of 200 ° C. and completely flowing out the theoretical amount of water, 90 g of ethylene glycol and 0.1 g of tetrabutyl titanate as a catalyst were added to the 500 ml Erlenmeyer flask, and the temperature was raised in a nitrogen stream. The reaction is carried out for 2 hours at < RTI ID = 0.0 > Then, 0.1 g of antimony acetate, 0.2 g of dibutyl tin oxide, 0.07 g of tetrabutyl titanate, and 0.2 g of trimethyl phosphate were added as a stabilizer. Then, the temperature was raised and the polycondensation reaction was performed for 140 minutes at 245 degreeC under reduced pressure of 0.3 Torr. The sample collected at this time had a melt index (190 ° C., 2160 g) of 3, a number average molecular weight of 37,000, a weight average molecular weight of 390,000, and a melting point of 45 ° C. measured by the DSC method.

Example 2

The 500 ml Erlenmeyer flask was replaced with nitrogen, and then 146 g of adipic acid and 2 g of aminosalicylicacid were added, followed by esterification while gradually raising the temperature to allow water to flow out. At this time, after fixing at a temperature of 200 ° C. and completely flowing out the theoretical amount of water, 90 g of ethylene glycol and 0.1 g of tetrabutyl titanate as a catalyst were added to the 500 ml Erlenmeyer flask, and the temperature was raised in a nitrogen stream. The reaction is carried out for 2 hours at < RTI ID = 0.0 > Then, 0.1 g of antimony acetate, 0.2 g of dibutyl tin oxide, 0.07 g of tetrabutyl titanate, and 0.2 g of trimethyl phosphate were added as a stabilizer. Subsequently, the temperature was raised and the polycondensation reaction was carried out at 245 ° C. under a reduced pressure of 0.3 Torr for 200 minutes. The sample thus obtained had a melt index (190 ° C, 2160g) of 5, a number average molecular weight of 37,400, a weight average molecular weight of 250,000, and a melting point of 45 ° C measured by the DSC method.

Example 3

After replacing the 500 ml Erlenmeyer flask with nitrogen, 132.6 g of adipic acid, 11.8 g of succinic acid, and 3 g of 2-amino-5-hydroxybenzoic acid were added, and the esterification reaction was carried out while gradually raising the temperature to allow water to flow out. At this time, after fixing at a temperature of 200 ° C. and completely flowing out the theoretical amount of water, 130 g of 1,4-butanediol and 0.1 g of tetrabutyl titanate as a catalyst were added to the 500 ml Erlenmeyer flask to increase the temperature in a nitrogen stream. Then, the reaction is carried out at 200 ° C. for 2 hours to allow the theoretical amount of water to flow out. Then, 0.1 g of antimony acetate, 0.2 g of dibutyl tin oxide, 0.07 g of tetrabutyl titanate, and 0.2 g of trimethyl phosphate were added as a stabilizer. Then, the temperature was raised and the polycondensation reaction was performed for 190 minutes at 245 degreeC under reduced pressure of 0.3 Torr. The sample collected at this time had a melt index (190 ° C, 2160g) of 8, a number average molecular weight of 410,000, and a weight average molecular weight of 290,000, and the melting point measured by the DSC method was 50 ° C.

Example 4

The 500 ml Erlenmeyer flask was replaced with nitrogen, and then 146 g of adipic acid and 4 g of 3-chloro-l-tyrogzne were added, followed by esterification while gradually raising the temperature to allow water to flow out. At this time, after fixing at a temperature of 200 ° C. and completely flowing out the theoretical amount of water, 130 g of 1,4-butanediol and 0.1 g of tetrabutyl titanate as a catalyst were added to the 500 ml Erlenmeyer flask to increase the temperature in a nitrogen stream. Then, the reaction is carried out at 200 ° C. for 2 hours to allow the theoretical amount of water to flow out. Then, 0.1 g of antimony acetate, 0.2 g of dibutyl tin oxide, 0.07 g of tetrabutyl titanate, and 0.2 g of trimethyl phosphate were added as a stabilizer. Then, the temperature was raised and polycondensation reaction was performed for 160 minutes at 245 degreeC under reduced pressure of 0.3 Torr. The sample thus collected had a melt index (190 ° C, 2160g) of 4, a number average molecular weight of 347,000, a weight average molecular weight of 380,000, and a melting point of 59 ° C measured by the DSC method.

Example 5

The 500 ml Erlenmeyer flask was replaced with nitrogen, and then 146 g of adipic acid and 3 g of 3-amino-4-hydroxybenzoic acid were added, followed by esterification while gradually raising the temperature to allow water to flow out. At this time, after fixing at a temperature of 200 ° C. and completely flowing out the theoretical amount of water, 130 g of 1,4-butanediol and 0.1 g of tetrabutyl titanate as a catalyst were added to the 500 ml Erlenmeyer flask to increase the temperature in a nitrogen stream. Then, the reaction is carried out at 200 ° C. for 2 hours to allow the theoretical amount of water to flow out. Then, 0.1 g of antimony acetate, 0.2 g of dibutyl tin oxide, 0.07 g of tetrabutyl titanate, and 0.2 g of trimethyl phosphate were added as a stabilizer. Then, the temperature was raised and polycondensation reaction was performed for 170 minutes at 245 degreeC under reduced pressure of 0.3 Torr. The sample collected at this time had a melt index (190 ° C, 2160g) of 11, a number average molecular weight of 35,300, and a weight average molecular weight of 217,000, and the melting point measured by the DSC method was 59 ° C.

Comparative Example 1

After replacing the 500 ml Erlenmeyer flask with nitrogen, 108 g of 1,4-butanediol and 118 g of succinic acid were added thereto. The temperature was raised in a nitrogen stream, and nitrogen was stopped at 140 to 200 ° C. for 5 hours, and esterification reaction was carried out by condensation over 1.5 hours under a reduced pressure of 20 to 2 mmHg.

At this time, the number average molecular weight of the sample collected was 4,900, and the weight average molecular weight was 11,200.

Subsequently, 0.2 g of catalyst tetraisopropyltitanium was added under an atmospheric nitrogen stream. And the temperature was raised and the deglycol reaction was performed for 6 hours under reduced pressure of 15-0.2 mmHg at the temperature of 220 degreeC. The sample collected had a number average molecular weight of 16,100 or a weight average molecular weight of 44,100. Melting | fusing point measured by the DSC method of the said sample is 118 degreeC.

Comparative Example 2

After replacing the 500 ml Erlenmeyer flask with nitrogen, 92 g of ethylene glycol, 118 g of succinic acid, and 0.07 g of catalyst tetrabutyl titanate were added thereto. The temperature was raised in a nitrogen stream, and nitrogen was stopped at 200 ° C. for 2 hours to carry out esterification by condensation over 0.5 hours under a reduced pressure of 20 to 2 mmHg.

Subsequently, 0.07 g of catalyst tetrabutyl titanate, 0.45 g of dibutyl tin oxide, and 0.2 g of trimethyl phosphate as stabilizers were added under a nitrogen stream at atmospheric pressure. The deglycol reaction was performed for 18 hours under reduced pressure of 15-0.2 mmHg at the temperature of 250 degreeC. The sample collected had a number average molecular weight of 9,000 or a weight average molecular weight of 32,000. Melting | fusing point measured by the DSC method of the said sample is 100 degreeC.

Comparative Example 3

After replacing the 500 ml Erlenmeyer flask with nitrogen, 108 g of 1,4-butanediol, 21.9 g of adipic acid and 100.3 g of succinic acid were added thereto. The temperature was raised in a nitrogen stream, and nitrogen was stopped at 200 ° C. for 2 hours to carry out esterification by condensation over 0.5 hours under a reduced pressure of 20 to 2 mmHg.

Subsequently, 0.07 g of catalyst tetraisopropyltitanium, 0.45 g of dibutyl tin oxide, and trimethyl phosphate as a stabilizer were added under a nitrogen stream at atmospheric pressure. The temperature was raised and deglycol reaction was performed for 3.2 hours under reduced pressure of 15-0.2 mmHg at the temperature of 250 degreeC. The sample collected had a number average molecular weight of 31,000 or a weight average molecular weight of 84,000. Melting | fusing point measured by the DSC method of the said sample is 95 degreeC.

[Comparative Example 4]

After replacing the 500 ml Erlenmeyer flask with nitrogen, 92 g of ethylene glycol, 118 g of succinic acid, 0.5 g of glycerin, and 0.07 g of catalytic tetrabutyl titanate were added thereto. The temperature was raised in a nitrogen stream, and nitrogen was stopped at 200 ° C. for 2 hours to carry out esterification by condensation over 0.5 hours under a reduced pressure of 20 to 2 mmHg.

Subsequently, 0.07 g of catalyst tetrabutyl titanate, 0.45 g of dibutyl tin oxide, 0.25 g of stabilizer trimethyl phosphate, and 0.2 g of tetraisopropyl titanium were added under an atmospheric nitrogen stream. The temperature was raised and deglycol reaction was performed for 2.5 hours under reduced pressure of 15-0.2 mmHg at the temperature of 250 degreeC. The sample collected had a number average molecular weight of 27,000 or a weight average molecular weight of 221,000. Melting | fusing point measured by the DSC method of the said sample is 99 degreeC.

To prepare a polyester resin by the method of Examples 1 to 5 using the method according to the invention, compared to the polyester resin prepared according to the conventional method the content of the composition and the analysis results according to the following Table 2 Shown in In the present invention, the melting point was measured using a PerkinElmer DSC at a heating rate of 10 ° C. per minute, and the melt index (MELT INDEX) was measured at 2,160 g load at 190 ° C. according to the KS method. In addition, molecular weight was measured by GPC.

As can be seen in Table 2, it can be seen that the polyester resin composition according to the present invention has a high number average molecular weight and a weight average molecular weight, a low melt index, and excellent physical properties such as tear strength.

[Effects of the Invention]

According to the present invention, the dicarboxylic acid component and the monomer are reacted first, and then, glycol is added to the reaction product, followed by a three step reaction of polycondensation through esterification or transesterification. A biodegradable polyester resin composition having a molecular weight and a method for producing the same are provided.

By adding and reacting the reactants in the steps described above, the problem of abrupt increase and gelation of low molecular weight polyester, which is conventionally caused by adding a polyfunctional monomer together with the dicarboxylic acid and the glycol, is solved. can do.

In addition, since the polyester resin according to the present invention has excellent tear strength, it is possible to solve the limitation on practical use that has occurred due to the lack of tear strength in the past. For example, it is difficult to manufacture and use a garbage bag and a shopping bag with an existing aliphatic polyester resin, so it is difficult to tear, but the polyester according to the present invention has improved tearing strength by an amine group present in a molecule, thereby enabling practical use. .

As such biodegradable polyester is put to practical use, it is decomposed by microorganisms at the time of disposal and finally remains as carbon dioxide and water, thereby solving the problem of plastic, which is the main culprit of global environmental pollution.

Claims (2)

(1) aliphatic (including cyclic aliphatic) containing adipic acid; (2) aliphatic (cyclic aliphatic) containing any one or more selected from 1,4-butanediol and ethylene glycol; Condensation reaction and esterification reaction in the presence of a monomer containing glycol as a main component and each having at least one hydroxyl group, an amine group and a carboxyl group as functional groups of 0.1 to 50% by weight relative to the theoretical weight of polyester. And the number average molecular weight obtained by the polycondensation reaction after one or two or more selected from the transesterification reaction, the weight average molecular weight is 160,000 ~ 600,000, the melting point is 45 ~ 60 ℃, melt viscosity ( 190 ℃, 2160g) is 0.1-50, and as the monomer 3-amino-4-hydroxybenzoic acid, 4-amino-3-hydroxybenzoic acid, 2-amino-5-hydroxybenzoic acid, aminosalicylic acid, 3-chloro-L -tyrosine, L-3- (3,4-d Polyester resin compound, characterized in that any one or a mixture of two or more selected from ihydroxyphenyl) alanine is used. (1) an aliphatic (including cyclic aliphatic) dicarboxylic acid (or anhydride thereof) containing adipic acid, and 0.1 to 50% by weight of (2) functional groups as the functional weight of a hydroxyl group, an amine group, and A first step of conducting any one or two or more reactions selected from condensation reaction, esterification reaction, and transesterification reaction at a temperature of 160 to 240 ° C. by adding a monomer containing one or two or more carboxyl groups, and the first Step 2 A second step of performing an esterification reaction or a transesterification reaction at a temperature of 200-220 ° C. by adding an aliphatic (including cyclic aliphatic) glycol including any one or more selected from 1,4-butanediol and ethylene glycol to the reaction product. And a third polycondensation of the polyester, which is the second step reaction product, at a temperature of 210 to 270 and a vacuum of 0.005 to 10 torr, to produce a high molecular weight polyester. Polyester resin manufacturing method characterized in that consisting of steps.