KR101170506B1 - Process for Preparing Bis2-hydroxyethylterephthalate from Waste Polyethyleneterephthalate - Google Patents
Process for Preparing Bis2-hydroxyethylterephthalate from Waste Polyethyleneterephthalate Download PDFInfo
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- KR101170506B1 KR101170506B1 KR1020090067595A KR20090067595A KR101170506B1 KR 101170506 B1 KR101170506 B1 KR 101170506B1 KR 1020090067595 A KR1020090067595 A KR 1020090067595A KR 20090067595 A KR20090067595 A KR 20090067595A KR 101170506 B1 KR101170506 B1 KR 101170506B1
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- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
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Abstract
본 발명은 폐 폴리에틸렌테레프탈레이트를 이용한 폴리에스테르 비스(2-하이드록시에틸)테레프탈레이트의 제조방법에 관한 것이다. 본 발명의 폐 폴리에틸렌테레프탈레이트를 이용한 비스(2-하이드록시에틸)테레프탈레이트를 제조하는 방법은, 폐 PET를 분쇄한 다음, 에틸렌글리콜을 가하고 고온, 고압의 초임계 상태(supercritical state)에서 20 내지 45분 동안 반응시키는 공정을 포함한다. 본 발명의 비스(2-하이드록시에틸)테레프탈레이트를 제조하는 방법에 의하면, 폐 PET로 부터 폴리에스테르 원료물질인 비스(2-하이드록시에틸)테레프탈레이트(BHET)의 고수율 대량생산이 가능하다. The present invention relates to a method for producing polyester bis (2-hydroxyethyl) terephthalate using waste polyethylene terephthalate. The method for producing bis (2-hydroxyethyl) terephthalate using waste polyethylene terephthalate of the present invention comprises pulverizing waste PET, and then adding ethylene glycol and adding 20 to 20 in a supercritical state at a high temperature and high pressure. 45 minutes reaction. According to the method for producing bis (2-hydroxyethyl) terephthalate of the present invention, it is possible to mass-produce high yield of bis (2-hydroxyethyl) terephthalate (BHET), a polyester raw material, from waste PET. .
폐 폴리에틸렌테레프탈레이트, 초임계 해당공정, 폴리에스테르 비스(2-하이드록시에틸)테레프탈레이트 Waste polyethylene terephthalate, supercritical glycolysis, polyester bis (2-hydroxyethyl) terephthalate
Description
본 발명은 폐 폴리에틸렌테레프탈레이트(poly(ethyleneterephthalate), PET)를 이용한 비스(2-하이드록시에틸)테레프탈레이트(bis(2-hydroxyethyl) terephthalate, BHET)의 제조방법에 관한 것이다. 좀 더 구체적으로, 본 발명은 폐 폴리에틸렌테레프탈레이트를 분쇄한 다음, 초임계 해당공정(supercritical glycolysis)에 의해 폴리에스테르 원료물질인 폴리에스테르 비스(2-하이드록시에틸)테레프탈레이트를 제조하는 방법에 관한 것이다.The present invention relates to a method for producing bis (2-hydroxyethyl) terephthalate (BHET) using waste polyethylene terephthalate (poly (ethyleneterephthalate), PET). More specifically, the present invention relates to a method for preparing polyester bis (2-hydroxyethyl) terephthalate as a raw material of polyester by pulverizing waste polyethylene terephthalate and then supercritical glycolysis. will be.
PET는 테레프탈산(terephthalic acid, TPA) 또는 디메틸테레프탈레이트(dimethylterephthalate, DMT)를 원료로 하여 생성된 폴리에스테르로서, 고강도, 저중량, 가스(특히, 이산화탄소)에 대한 저투과성, 높은 광투과율, 대량생산의 특성을 가지는 것으로 알려져 있다. 1970년대 중반부터 PET는 미국과 캐나다, 서유 럽 등에서 음료수 병으로 널리 사용되어 왔으며, 최근에는 다양한 오디오와 비디오 테이프 및 섬유의 제조에도 이용되는 등 다양한 산업 및 생활분야에 자리잡기 시작하여, 수요와 소비량이 계속 증가할 것으로 예상된다. PET is a polyester produced from terephthalic acid (TPA) or dimethylterephthalate (DMT) as a raw material. It is known to have characteristics. Since the mid-1970s, PET has been widely used as a beverage bottle in the United States, Canada, and Western Europe. Recently, PET has been established in various industries and lifestyles, such as in the manufacture of various audio, video tapes, and textiles. This is expected to continue to increase.
한편, 이렇게 우수한 특성을 가지는 PET는 용이하게 자연 분해되지 않는 특성으로 인하여, 심각한 환경오염 문제를 야기시키는 것이 문제점으로 대두되어 왔다. 이러한 폐 PET를 재활용하는 방법으로는, 크게 물리적인 방법과 화학적인 방법이 알려져 있다. 물리적 재활용 방법은 PET 클립이나 플레이크 형태로 이용하는 것이고, 화학적인 방법은 중합된 폐 PET를 원료물질인 단량체(monomer) 또는 올리고머(oligomer)로 분해하기 위해서 사용하는 것이나, 산업적인 측면에서는 화학적인 방법을 이용하는 것이 더욱 바람직하다. On the other hand, PET having such excellent properties has been a problem that causes serious environmental pollution problem due to the property that does not easily decompose naturally. As a method of recycling such waste PET, a physical method and a chemical method are known. The physical recycling method is used in the form of PET clips or flakes, and the chemical method is used to decompose the polymerized waste PET into a monomer or oligomer as a raw material. It is more preferable to use.
그동안 개발된 화학적인 방법으로는, 메탄올 분해(methanolysis), 해당공정 (glycolysis), 가수분해(hydrolysis), 가아미노 분해(aminolysis), 가암모니아 분해(ammonolysis) 등이 있는데, 이들 방법 중 메탄올 분해, 해당공정, 가수분해 등이 가장 널리 이용되고 있다. 그러나, 상기 분해방법 중 메탄올 분해와 가수분해는 PET를 분해할시 생성된 제품의 품질과 양이 극히 제한적이며, 분해 반응시간이 길고, PET 합성의 원료물질인 TPA 또는 DMT 중 한 종류만 생산하여 이들을 원료로 하는 각 PET 생산공정에 제한적으로 사용될 수 밖에 없다는 단점을 가진다. Chemical methods developed in the past include methanolysis, glycolysis, hydrolysis, aminolysis and ammonolysis, among which methanolysis, Glycolysis and hydrolysis are the most widely used. However, methanol decomposition and hydrolysis of the decomposition method is extremely limited in the quality and quantity of the product produced when decomposing PET, the decomposition reaction time is long, and only one type of TPA or DMT which is a raw material of PET synthesis It has a disadvantage that it can only be limited to each PET production process using these as raw materials.
따라서, 상술한 종래기술의 문제점을 해결하여, 메탄올 분해와 가수분해에 비하여 상대적으로 용이하게 BHET를 생산할 수 있는 해당공정을 이용한다면, 대량 으로 배출되는 폐 PET를 이용하여 새로운 PET 생산의 원료로 사용할 수 있을 것으로 예상되나, 아직까지는 이에 대한 보고가 전무한 실정이다.Therefore, by solving the problems of the prior art described above, if using the corresponding process that can produce BHET relatively easily compared to methanol decomposition and hydrolysis, it can be used as a raw material for the production of new PET using waste PET discharged in large quantities It is expected to be possible, but there are no reports on this.
본 발명자들은 상술한 종래기술의 문제점을 해결하기 위하여 예의 연구노력한 결과, 초임계 상태에서 용이하게 BHET를 제조할 수 있는 해당공정을 이용하면, PET의 해중합 반응에 의한 사용성, 융해성, 분산성이 우수한 폴리에스테르 원료물질인 단량체, 즉, 비스(2-하이드록시에틸)테레프탈레이트를 제조할 수 있음을 확인하고, 본 발명을 완성하게 되었다. The present inventors have made diligent research efforts to solve the above-mentioned problems of the prior art. As a result, using the corresponding process capable of easily producing BHET in a supercritical state, the usability, dissolvability, and dispersibility of PET by depolymerization reaction It was confirmed that the monomer, i.e., bis (2-hydroxyethyl) terephthalate, as an excellent polyester raw material could be prepared, and completed the present invention.
결국, 본 발명의 주된 목적은 초임계 해당공정을 이용하여 폐 폴리에틸렌 테레프탈레이트로 부터 비스(2-하이드록시에틸)테레프탈레이트를 제조하는 방법을 제공하는 것이다.After all, the main object of the present invention is to provide a method for producing bis (2-hydroxyethyl) terephthalate from waste polyethylene terephthalate using supercritical glycolysis.
본 발명에 따르면, 폐 PET를 재활용하여 얻어지는 해당공정의 원료물질인 에틸렌글리콜을 초임계 상태(supercritical state), 즉, 최소 온도가 719.70K, 최소 압력이 7.7Mpa이상의 조건에서 BHET를 제조한다. According to the present invention, BHET is produced in a supercritical state of ethylene glycol, which is a raw material of the process obtained by recycling waste PET, in a condition of a minimum temperature of 719.70 K and a minimum pressure of 7.7 Mpa or more.
본 발명의 비스(2-하이드록시에틸)테레프탈레이트를 제조하는 방법에 의하면, 폐 PET로 부터 새로운 PET를 생산하기 위한 원료물질인 비스(2-하이드록시에틸)테레프탈레이트(BHET)의 고수율 대량생산이 가능하다. 본 발명의 방법에 의하여 폐 PET를 재활용하여 제조한 BHET는 수용성으로, 폴리에스테르 수지를 제조하는 원료물질로 사용되며, 이렇게 제조된 폴리에스테르수지는 전자사진용 현상제, 잉크젯 잉크, 분체도료, 접착제, 수용성 섬유 가공제, 코팅제용 수지, 식품 보관용기, 음료수병, 등 다양한 소재로 사용할 수 있어 고부가 가치를 창출할 수 있을 뿐만 아니라, 재활용 기술향상 및 환경문제를 해결할 수 있는 장점이 있다. According to the method for producing bis (2-hydroxyethyl) terephthalate of the present invention, a high yield bulk of bis (2-hydroxyethyl) terephthalate (BHET), which is a raw material for producing new PET from waste PET Production is possible. BHET produced by recycling waste PET by the method of the present invention is water-soluble and is used as a raw material for producing a polyester resin, and the polyester resin thus prepared is an electrophotographic developer, inkjet ink, powder coating, adhesive , Water-soluble fiber processing agent, coating resin, food storage containers, beverage bottles, etc. can be used in a variety of materials can not only create a high value added, but also has the advantage of improving the recycling technology and environmental problems.
본 발명의 폐 폴리에틸렌테레프탈레이트를 이용한 비스(2-하이드록시에틸)테레프탈레이트를 제조하는 방법은, 폐 PET를 분쇄한 다음, 에틸렌글리콜을 가하고 고온, 고압의 초임계 상태(supercritical state)에서 20 내지 45분 동안 반응시키는 공정을 포함한다(참조: 도 1). 이때, PET는 일반적으로 TPA와 DMT 및 에틸렌글리콜(ethyleneglycol)로부터 합성된 중합체로서, 이에 한정되는 것은 아니나, 폐 PET 성형품, 폐 PET 섬유, 폐 PET필름, 폐 PET 음료수병 등 각종 폐 PET를 포함하며, 드라이아이스(dry ice)를 이용하여 유효직경이 10mm 이하로 분쇄시키는 것이 바람직하다. 반응은 오토클레이브(autoclave)에서 수행하며, 최종적인 반응 생성물(BHET)은 초임계 조건에서 20 내지 45분 동안 반응시킨 반응물을 차가운 물에 냉 각시켜 분산시킨 다음, 열을 가하여 물을 끓여주고 다시 냉각시켜 고체 화합물을 수득하는 것이 바람직하다. The method for producing bis (2-hydroxyethyl) terephthalate using waste polyethylene terephthalate of the present invention comprises pulverizing waste PET, and then adding ethylene glycol and adding 20 to 20 in a supercritical state at a high temperature and high pressure. The reaction is carried out for 45 minutes (see FIG. 1). In this case, PET is generally a polymer synthesized from TPA, DMT, and ethylene glycol (ethyleneglycol), but is not limited thereto, and includes various waste PET such as waste PET molded products, waste PET fiber, waste PET film, waste PET drinking water bottles, and the like. Using dry ice, the effective diameter is preferably pulverized to 10mm or less. The reaction is carried out in an autoclave, and the final reaction product (BHET) is cooled by dispersing the reactants reacted for 20 to 45 minutes in supercritical conditions in cold water, then heated to boil water and again It is preferred to cool to give a solid compound.
한편, 상기 초임계 온도조건은 719.7K 이상, 1300K 이하의 조건이 바람직한데, 1300K 이상이 되면, 반응기의 손상과 대량생산에 어려움이 있고, 719.7K 이하가 되면 초임계 조건에서 예상되는 고수율과 짧은 반응시간을 기대할 수 없다. 또한, 초임계 압력조건은 7.7Mpa 이상, 15Mpa 이하의 조건이 바람직한데, 15Mpa 이상이 되면, 반응기의 손상 및 반응기 제작의 비용이 증가하여 대량생산이 어려워 지고, 7.7Mpa 이하가 되면, 폐 PET의 원료화 반응시간이 길며 수율이 낮아 진다. 따라서, 가장 바람직하게는, 폐 PET를 드라이아이스(dry ice)를 이용하여 분쇄한 다음, 에틸렌글리콜을 가하고 719.7K 이상, 1300K 이하의 온도조건 및 7.7Mpa 이상 15Mpa 이하의 압력조건에서 30 내지 35분 동안 반응시키면, 90% 이상의 수율로 BHET를 수득할 수 있다. On the other hand, the supercritical temperature conditions are more than 719.7K, 1300K or less is preferable, when 1300K or more, there is a difficulty in the damage and mass production of the reactor, when it is less than 719.7K and the high yield expected in the supercritical conditions Short response times cannot be expected. In addition, the supercritical pressure condition is preferably 7.7Mpa or more and 15Mpa or less, but when it is 15Mpa or more, the damage of the reactor and the cost of the reactor production increase, making mass production difficult. The raw material reaction time is long and the yield is low. Therefore, most preferably, the waste PET is pulverized using dry ice, and then ethylene glycol is added, followed by 30 to 35 minutes at 719.7K or more, 1300K or less temperature conditions and 7.7Mpa or more and 15Mpa or less pressure conditions. Reaction can yield BHET in a yield of at least 90%.
이때, PET와 에틸렌글리콜 반응은 상기 화학식 1의 반응공정에 의하여 진행된다. 화학식 1은 본 발명의 폐 폴리에틸렌테레프탈레이트로부터 비스(2-하이드록시에틸)테레프탈레이트를 제조하는 화학반응 공정을 개략적으로 나타낸 것이다. 상기 화학식 1에서 보듯이, 폐 PET의 분해공정에서 비스(2-하이드록시에틸)테레프탈레이트를 생성하는 것이 목적이지만, 상기 공정에서 첫 번째 반응뿐만 아니라, 두 번째 반응으로 인하여 비스(2-하이드록시에틸)테레프탈레이트이외의 생성물이 분해과정에서 제조되어, 화학식 1에 나타낸 여러 반응물 중 비스(2-하이드록시에틸)테레프탈레이트의 비율이 90%이상 생성된다. At this time, the PET and ethylene glycol reaction is carried out by the reaction process of the formula (1). Formula 1 schematically illustrates a chemical reaction process for preparing bis (2-hydroxyethyl) terephthalate from waste polyethylene terephthalate of the present invention. As shown in Chemical Formula 1, the purpose is to produce bis (2-hydroxyethyl) terephthalate in the decomposition process of waste PET, but the bis (2-hydroxy due to the second reaction as well as the first reaction in the process. Products other than ethyl) terephthalate are prepared in the decomposition process, and the ratio of bis (2-hydroxyethyl) terephthalate in the various reactants shown in Formula 1 is 90% or more.
이하, 실시예를 통하여 본 발명을 보다 상세히 설명하고자 한다. 이들 실시예는 오로지 본 발명을 보다 구체적으로 설명하기 위한 것으로, 본 발명의 요지에 따라 본 발명의 범위가 이들 실시예에 의해 제한되지 않는다는 것은 당업계에서 통상의 지식을 가진 자에게 있어서 자명할 것이다.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 of ordinary skill 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. .
우선, 범용으로 폐 PET를 재활용할 수 있는 방법을 연구하기 위하여, 각기 다른 3종류의 PET를 사용하여 동일한 실험을 진행한 후, BHET의 수율에 대한 실험을 진행하였다. First, in order to study a method for recycling waste PET for general purpose, the same experiment was conducted using three different types of PET, and then an experiment on the yield of BHET was conducted.
실시예 1: 폐 PET를 이용한 BHET의 제조 Example 1 Preparation of BHET Using Waste PET
폐 PET((주)SK화학, 도 2에 분자량 분포를 나타냄) 펠렛을 믹서기에 넣고 유리전이 온도 이하로 낮추어 PET가 쉽게 분쇄되도록 드라이 아이스를 넣어 1시간 동안 방치하였다. 그런 다음, 0.3g의 분쇄된 PET 및 5.0g의 에틸렌글리콜을 오토클레이브(autoclave)에 넣어 723K에서 20 내지 45분 동안 반응시키고, 꺼내어 차가운 물에서 식혀 분산시켜 주었다. 이어, 열을 가하여 용액의 온도를 증가시켜 물을 끓여 주었다. 이때, 끓는 물을 이용하는 이유는, BHET는 끓는 물에서 완전히 용해되지만, 반응되지 않은 올리고머들은 물에 용해되지 않아 손쉽게 생성된 BHET를 분리할 수 있고, 끓는 물에 녹았던 BHET는 물의 온도를 낮추어 주면 BHET가 결정화 되어 쉽게 분리가 가능하도록 해주는 역할을 한다. 반응 생성물인 비스(2-하이드록시에틸)테레프탈레이트(bis(2-hydroxyethyl)terephthalate, BHET)를 정량분석하기 위하여, 물과 테트라하이드로퓨란(tetrahydrofuran)이 50:50(부피비)으로 혼합된 용액에 용해시켜, 고성능 액체크로마토그래피(HPLC)로 분석하였다: 이때, HPLC조건은 분석물질을 20μl 투입하고, 0.8ml/min 유속의 THF/H2O를 용매로 Reverse-phase Zorbax-C8 컬럼을 사용하여 254nm에서 측정하였다. 그 결과, 반응 30분 후 폐 PET는 90% 이상의 수율로 BHET로 변환되었는 바, 단시간에 대량의 BHET가 생성함을 알 수 있었다. Waste PET (SK Chemical Co., Ltd., showing molecular weight distribution in FIG. 2) pellets were placed in a blender and lowered below the glass transition temperature, and then left for 1 hour with dry ice so that PET was easily crushed. Then, 0.3 g of crushed PET and 5.0 g of ethylene glycol were placed in an autoclave, reacted at 723 K for 20 to 45 minutes, taken out, and cooled and dispersed in cold water. Then, heat was applied to increase the temperature of the solution to boil water. At this time, the reason for using boiling water is that BHET is completely dissolved in boiling water, but unreacted oligomers are not dissolved in water, and thus, easily generated BHET can be separated, and BHET dissolved in boiling water lowers the temperature BHET is crystallized and plays a role in making it easy to separate. To quantify the reaction product, bis (2-hydroxyethyl) terephthalate (BHET), water and tetrahydrofuran were mixed in a 50:50 (volume ratio) solution. Dissolved and analyzed by high performance liquid chromatography (HPLC): HPLC conditions were performed using 20 μl of analyte and using a reverse-phase Zorbax-C8 column with THF / H 2 O at 0.8 ml / min flow rate as a solvent. Measured at 254 nm. As a result, the waste PET was converted into BHET at a yield of 90% or more after 30 minutes, and it was found that a large amount of BHET was produced in a short time.
실시예 2: 폐 PET 혼합물질을 이용한 BHET의 제조 Example 2 Preparation of BHET Using Waste PET Blend
폐 PET 혼합물질(다양한 종류의 폐 PET 병을 분쇄한 시료, 도 2에 분자량 분포를 나타냄)를 드라이아이스를 이용하여 칩(chip)의 형태로 분쇄한 다음, 0.3g의 분쇄된 PET와 5.0g의 에틸렌글리콜을 오토클레이브에 넣어 723K에서 20 내지 45분 동안 반응시키고, 오토클레이브를 차가운 물에서 식혀주었다. 반응 생성물인 비스(2-하이드록시에틸)테레프탈레이트(BHET)를 정량분석하기 위하여, 물과 테트라하이드로퓨란(tetrahydrofuran)이 50:50(부피비)으로 혼합된 용액에 용해시켜, 실시예 1에서와 동일한 조건에서 고성능 액체크로마토그래피(HPLC)로 분석하였다. 그 결과, 반응 20 내지 45분 후 폐 PET는 90% 이상의 수율로 BHET로 변환되었는 바, 단시간에 대량의 BHET가 생성함을 알 수 있었다. The waste PET mixture (samples of various kinds of waste PET bottles, shown in the molecular weight distribution in FIG. 2) was ground into chips using dry ice, followed by 0.3 g of crushed PET and 5.0 g Ethylene glycol was added to the autoclave and reacted at 723 K for 20 to 45 minutes, and the autoclave was cooled in cold water. In order to quantify the reaction product bis (2-hydroxyethyl) terephthalate (BHET), water and tetrahydrofuran were dissolved in a mixed solution at 50:50 (volume ratio), Analysis was performed by high performance liquid chromatography (HPLC) under the same conditions. As a result, the waste PET was converted to BHET in a yield of 90% or more after 20 to 45 minutes, it was found that a large amount of BHET is produced in a short time.
실시예 3: 폐 PET 병을 이용한 BHET의 제조 Example 3 Preparation of BHET Using Waste PET Bottles
코카콜라 음료수 폐 PET 병(도 2에 분자량 분포를 나타냄)을 드라이아이스를 이용하여 분말 형태로 분쇄한 다음, 0.3g의 분쇄된 PET와 5.0g의 에틸렌글리콜을 오토클레이브에 넣어 723K에서 20 내지 45분 동안 반응시키고, 오토클레이브를 차가운 물에서 식혀주었다. 반응 생성물인 비스(2-하이드록시에틸)테레프탈레이트(BHET)를 정량분석하기 위하여, 물과 테트라하이드로퓨란(tetrahydrofuran)이 50:50(부피비)으로 혼합된 용액에 용해시켜 고성능 액체크로마토그래피(HPLC)로 분석하였다. 그 결과, 반응 20 내지 45분 후 폐 PET는 90% 이상의 수율로 BHET로 변환되었는 바, 단시간에 대량의 BHET가 생성함을 알 수 있었다. The Coca Cola beverage waste PET bottle (showing the molecular weight distribution in FIG. 2) was ground in powder form using dry ice, and then 0.3 g of crushed PET and 5.0 g of ethylene glycol were placed in an autoclave for 20 to 45 minutes. And the autoclave was cooled in cold water. To quantify the reaction product bis (2-hydroxyethyl) terephthalate (BHET), water and tetrahydrofuran were dissolved in a 50:50 (volume ratio) solution and mixed with high performance liquid chromatography (HPLC). ). As a result, the waste PET was converted to BHET in a yield of 90% or more after 20 to 45 minutes, it was found that a large amount of BHET is produced in a short time.
실시예 4: BHET의 반응시간에 따른 수율의 변화 Example 4 Change in yield with reaction time of BHET
상기 실시예 1-3의 방법을 이용하여 제조된 BHET의 반응시간에 따른 수율의 변화를 확인하였다(참조: 표 1) The change in yield according to the reaction time of the prepared BHET using the method of Example 1-3 was confirmed (see Table 1).
도 3은 본 발명의 표 1의 실험방법에 의해 제조된 비스(2-하이드록시에틸)테레프탈레이트의 수율을 나타내는 그래프이다. 도 3의 그래프에서 보듯이, 반응시간이 30분 이후에도 BHET 생성물을 얻을 수 있지만, 반응시간이 30 내지 35분 사이에 BHET의 최대수율을 얻을 수 있음을 확인하였다. 3 is a graph showing the yield of bis (2-hydroxyethyl) terephthalate prepared by the experimental method of Table 1 of the present invention. As shown in the graph of Figure 3, the reaction time is obtained even after 30 minutes BHET product, it was confirmed that the maximum yield of BHET can be obtained between the
이상, 본 발명을 바람직한 실시예를 참조하여 설명하였지만, 당해 기술 분야의 숙련된 당업자라면 하기의 특허청구범위에 기재된 본 발명의 사상 및 영역으로부터 벗어나지 않는 범위 내에서, 본 발명을 다양하게 변경시킬 수 있음을 이해할 수 있을 것이다.Although the invention has been described above with reference to preferred embodiments, those skilled in the art can variously change the invention without departing from the spirit and scope of the invention as set forth in the claims below. I can understand that.
도 1은 본 발명의 폐 폴리에틸렌테레프탈레이트로부터 비스(2-하이드록시에틸)테레프탈레이트를 제조하는 공정을 개략적으로 나타낸 그림이다. 1 is a schematic diagram illustrating a process for preparing bis (2-hydroxyethyl) terephthalate from waste polyethylene terephthalate of the present invention.
도 2는 본 발명에서 사용된 폐 폴리에틸렌테레프탈레이트의 평균 분자량을 나타내는 그래프이다. Figure 2 is a graph showing the average molecular weight of the waste polyethylene terephthalate used in the present invention.
도 3은 본 발명의 방법에 있어서, 반응시간에 따른 비스(2-하이드록시에틸)테레프탈레이트의 제조수율을 나타내는 그래프이다. 3 is a graph showing the production yield of bis (2-hydroxyethyl) terephthalate according to the reaction time in the method of the present invention.
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