KR20080001053A - Biodegradable aliphatic polyester resin compositionand preparation thereof on the excellence of bionics adapt - Google Patents

Abstract

A biodegradable aliphatic polyester composition having excellent biocompatibility is provided to obtain a non-toxic resin decomposed into water and carbon dioxide in vivo, having excellent moldability, mechanical strength, flexibility and controlled decomposition rate, and useful as absorbable suture, drug carriers or other medical materials. A biodegradable aliphatic polyester composition is obtained from main ingredients containing an aliphatic dicarboxylic acid including succinic acid and an aliphatic glycol that is a mixture formed of at least two dicarboxylic acids in 1,4-butanediol and ethylene glycol, in the presence of an organic compound catalyst obtained by adding 0.1-2.0 g of a tetrahydric alcohol compound having a long aliphatic backbone derived from aleuritic acid and ethylene glycol functional groups per mole of the aliphatic dicarboxylic acid; 0.0001-0.002 g of a titanate-based organometallic catalyst per mole of the aliphatic dicarboxylic acid; and 0.5-1 parts by weight of a phosphate-based stabilizer per part by weight of the metal catalyst. The biodegradable aliphatic polyester composition has a number average molecular weight of 45,000-120,000, a weight average molecular weight of 200,000-500,000, a melting point of 50-120 deg.C and a melt index of 0.5-30(190 deg.C, 2,160 g).

Description

Biodegradable aliphatic polyester composition with excellent biocompatibility and preparation method thereof {BIODEGRADABLE ALIPHATIC POLYESTER RESIN COMPOSITIONAND PREPARATION THEREOF ON THE EXCELLENCE OF BIONICS ADAPT}

The present invention relates to a biodegradable aliphatic polyester composition excellent in biocompatibility and a method for producing the same. The composition proposed by this invention is a composition of a high molecular weight biodegradable aliphatic polyester in which no toxicity is expressed in the body. The composition of the present invention is a biodegradable aliphatic polyester composition which is biodegradable and has excellent moldability and can be injected or extruded in the form of fibers, films and injection molding.

Conventionally, the composition of aliphatic polyester is a high molecular weight biodegradable compound that does not express toxicity in the body, and has been provided as a commodity such as surgical sutures, artificial blood vessels, artificial bones, drug carriers, etc. in the medical field.

Surgical suture materials widely used in the medical field are both natural polymer and polypropylene synthetic polymer materials. Recently, the provision of biodegradable polymer material medical supplies that decompose in the body environment such as moisture, microorganisms, enzymes, etc. contributes to the development of precise and complex medical technology.

Polyglycolide (Polyglycolide) as such a biodegradable polymer material; Polyglyconet, which is a copolymer of glycolide and trimethylene carbonate; Polyglactin, a copolymer of lactic acid and glycolic acid; Polyglycapron, which is a copolymer of polydioxanonone and glycolide-epsilon-caprolactone, is used.

Polyglycolide and polyglycine lack softness and resilience and cannot be used if sutures are made from monofilaments. This material is used as sutures to manufacture and braid multifilaments to compensate for shortcomings.

When the absorbent yarn is made of a polymer material obtained by block copolymerization of polylactic acid and hydrophilic polyethylene glycol, the water content of the polyethylene glycol copolymer is not suitable for weakening the fiber strength. The absorbent sand thus prepared is not suitable due to its low absorption in the body.

Although US Pat. No. 4,224,946 discloses aliphatic / aromatic copolyesters as surgical sutures, these sutures may retain aromatic components, which are carcinogens, during the degradation after the procedure. In addition, it is difficult to manufacture and process absorbent yarns due to the slow cooling rate during processing, excessive flexibility and elongation rate, and low tensile strength, which is not suitable as a surgical suture.

Aliphatic polyesters without aromatics are similar to polyethylene and polypropylene, which are flexible and tensile strength, and are biodegradable because they are suitable for the mechanical properties of medical polymer materials required by absorbent sand, drug carriers, artificial bones, and artificial joints. It is being used as a material for plastics. However, in order to give excellent physical properties and processability, a polymer having an average molecular weight of 30,000 or more is required. In the prior art, in order to obtain this molecular weight, a large amount of Sn, Zn, Sb-based metal catalysts and phosphorus-based stabilizers are included in the aliphatic polyester polymerization process, thereby causing toxicity in the body.

The present invention proposes an aliphatic polyester compound as a biocompatible compound having a novel structure and properties. The present invention proposes a resin having a number average molecular weight of 45,000 to 120,000 and a weight average molecular weight of 200,000 to 500,000 in the presence of a minimum metal catalyst and a method for producing the same. This invention proposes a biodegradable aliphatic polyester composition containing no carcinogen. This invention proposes a biodegradable aliphatic polyester composition without causing toxicity. This invention proposes a biocompatible aliphatic polyester compound having mechanical properties and processability at the general resin level.

High molecular weight aliphatic polyester

The researchers of this invention have prepared a new organic compound catalyst (II) for producing high molecular weight aliphatic polyester (I) in the presence of a minimum metal catalyst. The organic compound catalyst was given as a multifunctional compound having a long main chain and four hydroxyl groups by reacting eleuritic acid with ethylene glycol. The prepared compound catalyst is used as a main catalyst in the synthesis of aliphatic polyester. When the compound catalyst is added to the esterification reaction during the aliphatic polyester synthesis step, many reaction functional groups connect the polymer chain to a longer length during the aliphatic polyester polymerization. The aliphatic polyester thus obtained is an aliphatic polyester having a high molecular weight equivalent to that of a conventional aliphatic polyester, and furthermore, the aliphatic polyester of the present invention has a non-toxic biocompatibility, and a side chain of the polymer chain is an amorphous region of molecular structure. Good biodegradability is also given by increasing.

Organic Compound Catalyst (II)

An organic compound catalyst (II) is prepared for preparing a biodegradable resin composition which is the polymer aliphatic polyester (I) resin. The catalyst (II) of the present invention was charged with auritic acid in the reactor, ethylene glycol was added in a range of 1.2 mol to 1.8 mol with respect to 1 mol of the aureic acid, and then the temperature was increased to 200 ° C. under the tetrabutylene titanate catalyst (IV). Prepare by stirring while raising. Increasing the temperature in the above process produces the water quoted in Scheme 1 as a by-product. This water is removed and the remaining material is made of aliphatic polyhydric alcohol (III) and used as the organic compound catalyst (II) of the present invention. In the above process, the addition amount of the tetrabutylene titanate as the catalyst (IV) is 0.1 g to 0.15 g based on 1 mole of aureic acid. More preferably, it is 0.12g-0.13g.

In the preparation of the polyhydric alcohol organic compound catalyst (II), it is important to properly control the molar ratio of ethylene glycol and areuritic acid and the reaction temperature so as to suppress the autopolymerization of the areuritic acid molecule, and the ethylene glycol is the carboxyl group of the areuritic acid. To be able to combine. As the self-polymerization of the areuritic acid molecules increases, the end group decreases, thereby reducing the catalytic effect. If this condition is serious, the gelation of the resin proceeds in the synthesis of aliphatic polyester, the discharge of the resin from the reactor is impossible, and the final product cannot be processed. However, when ethylene glycol reacts properly to the carboxyl group of the aureic acid, as shown in Scheme 1, each hydroxyl group exhibits different activity, and the short hydroxyl group in the middle of the compound causes steric hindrance due to long chains on both sides of the functional group. The reaction proceeds to the extent that the gelation reaction does not proceed during the synthesis of the resin by lowering the reactivity of the resin. This reaction process produces short side chains in the resulting polyester resin chain, and this secondary reaction increases the reaction rate of the resin synthesis and increases the molecular weight distribution of the polyester, thereby improving the processability of the polyester resin obtained later, and the molecular structure. By increasing the amorphous region in the biodegradation function is also improved.

Main material of polyester

Aliphatic polyester (I) synthesized using the long-chain tetrahydric alcohol compound (III) synthesized by the above process as a catalyst (II) is an aliphatic (including cyclic aliphatic) dicarboxylic acid containing succinic acid as a main material ( Or anhydride thereof) and 1,4-butanediol. Preferably, succinic acid alone component and 1,4-butanediol; ② Succinic acid single component and ethylene glycol single component ③ Succinic acid single component 75 to 100 parts by weight, 1,4-butanediol and any one of the alkylene group (including cyclic alkylene group) glycol having 2 to 3 or 5 to 10 carbon atoms 25 To 0 to 0 parts by weight of a mixed material; ④ 75 to 100 parts by weight of any one of succinic acid and other dicarboxylic acids (dicarboxylic acids having 2 to 3 or 5 to 10 alkylene groups (including cyclic alkylene groups)) and 1,4-butanediol In a mixture of 100 to 0 parts by weight of the sole component of; Use either.

This invention will become clearer as it understands the process for producing the aliphatic polyester resin processed in two steps.

The first step is to obtain a catalyst (II), and to the reactor, an aliphatic (including cyclic aliphatic) dicarboxylic acid (or anhydride thereof) containing succinic acid and an aliphatic (including cyclic aliphatic) glycol monomer are introduced. Induce a transesterification reaction at a temperature of 180 ℃ to 200 ℃. The resulting material, water or methanol, is removed. The chemical reaction in this process is shown in Scheme 2. In Scheme 2 glycol is 1,4-butanediol and dicarboxylic acid is succinic acid.

Scheme 2 is a representative example of a chemical reaction in the reaction system. N in Scheme 2 is an integer from 1 to 50 as in Scheme 1.

The reaction molar ratio of dicarboxylic acid and glycol in Scheme 2 is 1: 1.2 to 1: 1.8. If the molar ratio is less than 1: 1.2, the reactivity decreases and the color is affected. If the molar ratio exceeds 1: 1.8, the cost increases. Considering two opposing aspects, the molar ratio of the preferred compound in Scheme 2 is 1: 1.3.

The second step is to obtain aliphatic polyester (I) using catalyst (II). In the second step, 0.1 g to 2.0 g per 1 mol of the tetrahydric alcohol (III) compound having the long aliphatic main chain shown in Scheme 1 is added to the aliphatic dicarboxylic acid (including the cycloaliphatic) as the main material, followed by The step reaction product is polycondensed with a polyester which is 120 to 360 minutes at a temperature of 240 to 260 ° C. and a vacuum of 0.05 to 2 torr to produce aliphatic polyester (I).

That is, the reaction product and the unreacted dicarboxylic acid component produced in the first step are each reacted with adjacent molecules while removing substances such as water, ethanol or glycol by the chemical reaction as in Scheme 2, respectively, and the number average molecular weight of 45,000 to 120,000. A polyester resin (I) having a weight average molecular weight of 200,000 to 500,000 is molded. However, the gelation of the synthesized aliphatic polyester occurs when the tetrahydric alcohol sulfide (III) having a long aliphatic main chain used at this time exceeds 2.0 g with respect to 1 mol of the dicarboxylic acid. When such a gelation reaction occurs, it is difficult to discharge the resin in the reactor, and even if discharged, the processing becomes impossible, thereby making it useless. On the contrary, when the amount of the tetrahydric alcohol sulfide (III) is less than 0.1 g per 1 mole of the aliphatic dicarboxylic acid, only a weak reaction is performed as a catalyst, and thus a sufficient high molecular weight resin cannot be obtained. Preferably, the amount of tetravalent alcohol sulfide (III) is 0.5 g to 1.0 g per mole of aliphatic dicarboxylic acid. An example of this polyester resin (I) formation reaction is shown in Scheme 3.

이고, m, n은 중합도를 나타내는 정수이다. 정수 m은 n보다 크다.In Scheme 3, A is

And m and n are integers showing degree of polymerization. The integer m is greater than n.

In the present invention, a catalyst may be added at the beginning or the end of the esterification reaction or transesterification reaction of the second step. At this time, the addition amount of a catalyst is 0.0001g-0.002g or less with respect to 1 mol of aliphatic dicarboxylic acid injected. If the added amount is less than 0.0001 g per 1 mole of aliphatic dicarboxylic acid, the esterification reaction is difficult, and if it exceeds 0.002 g, the theoretical amount of water, methanol or glycol is easily removed, but it is harmful to the living body due to the toxicity expressed from the catalyst. The quantity must be observed. As the catalyst, an organometallic compound containing titanate is used, and more preferably any one or two or more catalysts selected from tetrabutyl titanate and tetrapropyl titanate are used.

In addition, a stabilizer may be added between the beginning or the end of the second esterification reaction or transesterification reaction. The addition amount of the stabilizer is about the ratio of the stabilizer 0.5-1 with respect to the addition amount 1 of a metal catalyst by weight ratio. If the amount of the stabilizer is less than 0.5 ratio compared to the amount of the metal catalyst, the effect may not be obtained as a stabilizer, the color may deteriorate, and the reaction side reactant tetrahydrofuran may increase, causing toxicity to the product. When the amount of the stabilizer is more than 1 ratio of the amount of the metal catalyst, the reaction rate is long and it is difficult to obtain a high molecular weight polyester. As the stabilizer, one or more stabilizers of a phosphate system such as trimethyl phosphate, phospheric acid, and triphenyl phosphate are used.

As described above, the polyester resin of the present invention is a high molecular weight polymer through a two-step reaction. As described above, the number average molecular weight of the polyester resin provided in the present invention is 45,000 to 120,000, the weight average molecular weight is 200,000 to 500,000, the melting point is 50 to 120 ° C, and the melt index is 0.5 to 30 (190 ° C, 2160 g).

An embodiment of this invention is as follows. The present invention is not limited to the exemplified embodiments and various embodiments are included within the technical scope of the present invention.

Comparative Example 1

The air in the 500 ml Erlenmeyer flask was replaced with nitrogen. Into the Erlenmeyer flask, 108 g of 1,4-butanediol and 118 g of succinic acid were added. The temperature was raised in a nitrogen stream, and nitrogen was stopped at 140 to 200 ° C for 5 hours to induce an esterification reaction by condensation over 1.5 hours at 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 deglycol reaction was induced for 6 hours by the pressure of 15-0.2 mmHg at the temperature of 220 degreeC. The sample collected had a number average molecular weight of 16,100 and a weight average molecular weight of 44,100. 1.5 parts by weight of hexamethylene diisocyanate was added to 100 parts by weight of polyester in a kneader and pelletized at a working temperature of 180 to 200 ° C. The pellet sample had a number average molecular weight of 42,000 and a weight average molecular weight of 205,900, and the melting point measured by the DSC method was 118 ° C.

Comparative Example 2

The air in the 500 ml Erlenmeyer flask was replaced with nitrogen, 118 g of succinic acid and 4 g of 3-amino-4-hydroxybenzoic acid were added thereto, followed by esterification while gradually raising the temperature to allow water to flow out. When the temperature was 200 ° C., the temperature was fixed, and the theoretical amount of water was completely flowed out. Then, 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 was carried out for 2 hours to pour out the theoretical amount of water. In addition, 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. The temperature was further raised, the temperature was reduced to 0.3torr at 245 ° C, and condensation polymerization was carried out for 200 minutes. After the polycondensation, the sample had a melt index (190 ° C, 2160 g) of 12, a number average molecular weight of 32,000, a weight average molecular weight of 197,000, and a melting point of 97 ° C measured by DSC.

Comparative Example 3

The air in the 500 ml Erlenmeyer flask was replaced with nitrogen, 118 g of succinic acid and 12 g of amino salicylic acid were added thereto, and the temperature was gradually raised to induce an esterification reaction to inject water. After fixing the elevated temperature at 200 ° C. and completely distilling the theoretical amount of water, 92 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 a period of time to drain the theoretical amount of water. Again, 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. The temperature was further increased, the temperature was reduced to 0.3torr at 245 ° C, and condensation polymerization was performed for 150 minutes. Melt index (190 degreeC, 2160g) was 9, the number average molecular weight 33,000, the weight average molecular weight 240,000, and the melting point measured by the DSC method was 98 degreeC.

Comparative Example 4

The internal air of the 500 mL Erlenmeyer flask was replaced with nitrogen, and 100.3 g of 1,4-butanediol 108g succinic acid and 21.9 g of adipic acid were added thereto. The temperature was raised in a nitrogen stream, the nitrogen supply was stopped at 200 ° C. for 2 hours, and an esterification reaction was induced by condensation over 0.5 hours under a reduced pressure of 20 to 2 mmHg. Subsequently, 0.07 g of catalyst tetraisopropyl titanium, 0.45 g of dibutyltin oxide, and trimethyl phosphate as a stabilizer were added under a nitrogen stream at atmospheric pressure. The temperature was increased to reduce the pressure to 15-0.2 mmHg at a temperature of 250 ° C. and induce a deglycol reaction for 3.2 hours. 1.5 parts by weight of hexamethylene diisocyanate was added to 100 parts by weight of polyester in a kneader and pelletized at a working temperature of 180 to 200 ° C. The pellet sample had a number average molecular weight of 31,000 or a weight average molecular weight of 84,000, and the melting point measured by the DSC method of the sample was 95 ° C.

Example 1

Substitute the nitrogen in the 1000 mL first triangle flask with nitrogen, add 304.43 g of areuretic acid and 78.16 g of ethylene glycol, add 0.12 g of tetrabutylene titanate as a catalyst, and slowly raise the temperature at 200 ° C. Reaction was advanced and water was distilled out. When the theoretical amount of water was released, the reaction was terminated to synthesize a tetrahydric alcohol having an aliphatic long chain.

Nitrogen was replaced by internal air of another 500 mL second triangular flask, 118 g of succinic acid and 117.16 g of 1,4-butanediol were added, and 0.001 g of tetrabutyl titanate was added as a catalyst while gradually raising the temperature to 200 ° C. The reaction was carried out for 3 hours in order to drain the theoretical amount of water.

In addition, 0.6 g of an aliphatic long main chain tetrahydric alcohol prepared in the first triangle flask was added to 0.001 g of tetrabutylene titanate as a catalyst, and 0.001 g of trimethyl phosphate as a stabilizer to the second triangle flask. Subsequently, the temperature was raised and the temperature was reduced to 0.5 Torr at 255 ° C. and a condensation polymerization reaction was induced for 240 minutes. The resulting biodegradable resin had a melt index (190 占 폚 and 2160 g) of 3.0, a number average molecular weight of 58,000 and a weight average molecular weight of 153,000, and the melting point measured by the DSC method was 118 占 폚.

Example 2

Replace the inside of 500ml Erlenmeyer flask with nitrogen, add 1,4-butanediol 117.16g succinic acid 100.3g, adipic acid 21.9g, add 0.001g of tetrabutyl titanate as catalyst while gradually raising the temperature to 200 ° C After reacting for 3 hours in the air stream, the theoretical amount of water was flowed out to obtain an aliphatic long-chain tetrahydric alcohol. To 0.6 g of the produced aliphatic long main chain tetrahydric alcohol, 0.001 g of catalyst tetrabutylene titanate and 0.001 g of stabilizer trimethylphosphate were added. Then, the temperature was raised and the temperature induced a polycondensation reaction at 255 ° C. under a reduced pressure of 0.5 Torr for 192 minutes. The biodegradable resin samples of the resulting material had a melt index (190 DEG C and 2160 g) of 6.0, a number average molecular weight of 58,000, a weight average molecular weight of 153,000, and a melting point of 95 DEG C measured by the DSC method.

Example 3

The inside of the 500 ml Erlenmeyer flask was replaced with nitrogen, 117.16 g of 1,4-butanediol and 146.14 g of adipic acid were added, and 0.001 g of tetrabutyl titanate was added as a catalyst while gradually raising the temperature to 200 ° C. The reaction was carried out for a period of time to release the theoretical amount of water. To 0.8 g of an aliphatic long main chain tetrahydric alcohol prepared as described above, 0.001 g of tetrabutylene titanate was added as a catalyst and 0.001 g of trimethylphosphate as a stabilizer. The temperature was continuously raised to reduce the pressure of 0.5 Torr and induce a condensation polymerization reaction for 240 minutes when the temperature was 255 ° C. The resulting biodegradable resin sample had a melt index (190 ° C., 2160 g) of 0.8, a number average molecular weight of 72,000, a weight average molecular weight of 238,000, and a melting point of 60 ° C. measured by the DSC method.

Example 4

The aliphatic polyesters obtained in Comparative Examples 1 to 4 and Examples 1 to 3 were produced as monofilaments at working temperature of 180 ° C. to 220 ° C., draw ratio 6 times, and diameter of 0.25 mm in the extruder. Had had the result.

Monofilament Strength Measurement Table sample Comparative Example 1 Comparative Example 2 Comparative Example 3 Comparative Example 4 Example 1 Example 2 Example 3 Strength (kgf) 3.2 3.1 2.8 2.9 3.2 3.1 3.1

Example 5

The monofilament samples obtained in Example 4 were cut into 5 cm each and disinfected with ethylene oxide gas for 24 hours, and then inactivated 10% fetal bovine serum (FBS) in 1 liter of Bulbecco's minimum essential medium, and 2gm of sodium bicarbonate, 200 mM L-glutamine, HEPES 5.75 Gm and antibiotics (penicilline 10,000 U, Streptomycin 100 mg, amphotericin B 25 mg / ml) were added to the culture medium, and the cell line L929 was inoculated with 50.8x10 ⁴ individuals, and the number of proliferated cells was measured 5 days later. The results in Table 2 were obtained in comparison with the control.

Cell proliferation chart Cell count (x 10 ⁴ ) Control (blank) 182.75 Comparative Example 1 137.0 Comparative Example 2 138.2 Comparative Example 3 142.1 Comparative Example 4 137.2 Example 1 183.75 Example 2 187 Example 3 207

Example 6

The aliphatic polyester obtained in Comparative Examples 1 to 4 and Examples 1 to 3 was subjected to a pressure of 1.5 tons at a working temperature of 120 ° C. to 160 ° C. using a hot press to produce a film having a thickness of 100 μm, and the soil having a depth of 30 cm. After 8 weeks of reclamation, the biodegradability was measured by gravimetric analysis. Table 3 shows the measurement results.

Biodegradability Chart Initial weight (g) Weight after 8 weeks of landfill (g) Biodegradability (%) Comparative Example 1 11.21 1.08 90.4 Comparative Example 2 11.83 0.92 92.2 Comparative Example 3 11.54 1.01 91.2 Comparative Example 4 11.81 0.98 91.7 Example 1 11.32 1.01 91.1 Example 2 11.49 0.90 92.2 Example 3 11.82 0.96 91.9

As described above, according to the present invention, in the synthesis of aliphatic polyester, a low molecular weight generated by using a conventional polyfunctional monomer by adding a polyfunctional aliphatic alcohol having a hydrosil group with different activity as a chain extender to the reaction to obtain a product. The problem of abrupt increase of polyester and gelation was solved. In addition, the present invention was able to obtain a resin with excellent biocompatibility by using almost no harmful catalyst component to the human body used in the conventional aliphatic polyester synthesis process, and furthermore, it was possible to obtain a higher molecular weight aliphatic polyester. In addition, the present invention has almost the same mechanical properties of the resulting aliphatic polyester as the aliphatic polyester according to the prior art. Since the polyester resin composition produced in this invention is manufactured at low cost, medical absorbent sutures can be manufactured at low cost.

Claims (12)

A main material which is aliphatic glycol which is a mixture of aliphatic dicarboxylic acid containing succinic acid and dicarboxylic acid in 1,4-butanediol and ethylene glycol; An organic compound catalyst added with 0.1 g to 2.0 g of a tetravalent alcohol compound having an aliphatic long main chain prepared by using auritic acid as a functional group and ethylene glycol with respect to 1 mole of aliphatic dicarboxylic acid as the main material; 0.0001 g to 0.002 g of a titanate-based organometallic catalyst based on 1 mole of the aliphatic dicarboxylic acid; And a phosphate stabilizer based on 1 part by weight of the metal catalyst in the presence of 0.5 to 1 part by weight; A polyester resin composition having a number average molecular weight of 45,000 to 120,000, a weight average molecular weight of 200,000 to 500,000, a melting point of 50 to 120 ° C, and a melt viscosity of 0.5 to 30 (190 ° C, 2,160 g). The method of claim 1, wherein the main material is in one mole of the glycol; A polyester composition mixed and reacted at a ratio of 1.2 to 1.8 moles of the dicarboxylic acid. The dicarboxylic acid component of the main material is succinic acid; The glycol component is 1,4-butanediol; Polyester composition. The dicarboxylic acid component of the main material is succinic acid; Aliphatic glycol component is 1,4-butanediol; Polyester composition. The dicarboxylic acid component of the main material is succinic acid; The glycol component is ethylene glycol; Polyester resin composition. The dicarboxylic acid component of the main material is succinate; The glycol component is any one of glycol mixed with 1,4-butanediol and a mixed component of an alkylene group having 2 to 3 or 5 to 10 carbon atoms; Polyester resin composition. The polyester resin composition according to claim 6, wherein the other glycol is composed of 25 to 0 parts by weight based on 75 to 100 parts by weight of the 1,4-butanediol. The dicarboxylic acid component according to claim 1, wherein the dicarboxylic acid component is a mixed component of succinic acid and dicarboxylic acid having an alkylene group having 2 to 3 or 5 to 10 carbon atoms; A polyester resin composition comprising any one of mixed components of the 1,4-butanediol with a single component ethylene glycol. The dicarboxylic acid component of the main material is 75 to 100 parts by weight of succinic acid; Polyester resin composition which is a mixture of 25-0 weight part of other dicarboxylic acids. An absorbent suture made of the polyester resin composition according to claim 1. 10. A molded article provided by molding the polyester resin composition obtained in any one of claims 1 to 9 by extrusion or injection. Preparing a main material which is an aliphatic glycol which is a mixture of aliphatic dicarboxylic acid comprising succinic acid and dicarboxylic acid among 1,4-butanediol and ethylene glycol; Preparing a catalyst having 0.1 g to 2.0 g of a tetrahydric alcohol compound having an aliphatic long main chain prepared by using auritic acid and ethylene glycol as a functional group in one mole of the main material; Mixing a catalyst with the main material and reacting at least one of condensation reaction, esterification reaction and transesterification reaction; Inducing a polycondensation reaction; A method of producing a polyester resin composition having a number average molecular weight of 45,000 to 120,000, a weight average molecular weight of 200,000 to 500,000, a melting point of 50 to 120 ° C, and a melt viscosity of 0.5 to 30 (190 ° C, 2,160 g).