KR20030083777A - Poly(acryloyl pyrrole), poly(acryloyl chloride)-g-polypyrrole and synthesis - Google Patents
Poly(acryloyl pyrrole), poly(acryloyl chloride)-g-polypyrrole and synthesis Download PDFInfo
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Abstract
Description
본 발명은 플라스틱 축전지, 스마트 윈도우(smart window), 전자기파 차폐제 등에 사용되는 폴리아크릴로일 클로라이드-g-폴리피롤 공중합체, 그 전구체 및 제조방법에 관한 것이다.FIELD OF THE INVENTION The present invention relates to polyacryloyl chloride-g-polypyrrole copolymers used in plastic storage batteries, smart windows, electromagnetic wave shielding agents, and the like, precursors thereof, and methods of manufacturing the same.
전도성 고분자는 금속에 비하여 가볍고 산화환원 반응을 통하여 전기 에너지를 저장할 수 있으며, 산화상태를 조절해주면 색상의 변화가 일어나기 때문에 플라스틱 축전지, 스마트 윈도우, 전자기파 차폐재 등에 이용될 수 있다.Conductive polymers are lighter than metals and can store electrical energy through redox reactions, and can be used in plastic storage batteries, smart windows, electromagnetic shielding materials, etc., because color changes occur when the oxidation state is controlled.
그러나, 전도성 고분자는 기존의 고분자 재료에 비해 가공성, 유연성, 용해성 등의 성질이 취약한 단점이 있다.However, the conductive polymer has a disadvantage in that the properties such as processability, flexibility, solubility are weak compared to the conventional polymer material.
따라서, 물성이 좋은 범용성 고분자와 복합체 및 공중합체를 형성하여 전도성 고분자가 가지는 단점을 개선하고자 하는 연구가 진행되고 있다.Therefore, researches are being conducted to improve the disadvantages of the conductive polymer by forming a composite and a copolymer with a general purpose polymer having good physical properties.
그 중에서도 복합체에 관한 연구는 많이 행해지고 있지만 공중합체에 관한 연구는 별로 없다. 그리고, 복합체의 경우에는 공중합체에 비하여 전기전도도가 떨어지는 단점이 있다.Among them, many studies have been conducted on composites, but few studies on copolymers. In addition, the composite has a disadvantage in that electrical conductivity is lower than that of the copolymer.
따라서, 본 발명에서는 앞에서 언급한 전도성 고분자의 단점을 개선하면서 복합체에 비해 전기전도도가 우수한 폴리아크릴로일 클로라이드-g-폴리피롤을 제공하는 데 그 목적이 있다.Accordingly, an object of the present invention is to provide a polyacryloyl chloride-g-polypyrrole having excellent electrical conductivity compared to the composite while improving the disadvantages of the aforementioned conductive polymer.
또한, 본 발명은 상기와 같은 폴리아크릴로일 클로라이드-g-폴리피롤의 전구체인 폴리아크릴로일 피롤을 제공하는데도 그 목적이 있다.It is also an object of the present invention to provide a polyacryloyl pyrrole which is a precursor of the above polyacryloyl chloride-g-polypyrrole.
그리고, 본 발명은 폴리아크릴로일 피롤을 제조하는 방법을 제공하는데도 그 목적이 있다.The present invention also provides a method for producing a polyacryloyl pyrrole.
또한, 본 발명은 폴리아크릴로일 피롤로부터 폴리아크릴로일 클로라이드-g-폴리피롤을 제조하는 방법을 제공하는 데도 그 목적이 있다.It is also an object of the present invention to provide a method for producing polyacryloyl chloride-g-polypyrrole from polyacryloyl pyrrole.
상기와 같은 목적을 달성하기 위한 본 발명의 신규한 폴리아크릴로일 피롤은다음 화학식 1로 표시되며 분자량 1000 내지 500000인 것임을 그 특징으로 한다.The novel polyacryloyl pyrrole of the present invention for achieving the above object is represented by the following formula (1) is characterized in that the molecular weight of 1000 to 500000.
화학식 1Formula 1
상기 식에서, n은 1 내지 1000의 수이다.Wherein n is a number from 1 to 1000.
또한, 본 발명의 폴리아크릴로일 클로라이드-g-폴리피롤 공중합체는 다음 화학식 2로 표시되며 분자량 2000 ∼ 1000000 인 것임을 특징으로 한다.In addition, the polyacryloyl chloride-g-polypyrrole copolymer of the present invention is represented by the following formula (2) and characterized in that the molecular weight of 2000 ~ 1000000.
화학식 2Formula 2
상기 식에서, m과 n은 1 내지 1000의 수이다.Wherein m and n are numbers from 1 to 1000.
상기 화학식 1로 표시되는 폴리아크릴로일 피롤은 화학식 3으로 표시되는 피롤염과 다음 화학식 4로 표시되는 아크릴로일 클로라이드를 -20∼50℃에서 1 내지 24시간 동안 반응시킨 후, 개시제를 넣고 55∼75℃에서 1 내지 24시간 동안 반응시켜 얻어지는 것임을 그 특징으로 한다.The polyacryloyl pyrrole represented by the formula (1) is a pyrrole salt represented by the formula (3) and the acryloyl chloride represented by the following formula (4) for 1 to 24 hours at -20 to 50 ℃, and then put the initiator It is characterized in that it is obtained by reacting for 1 to 24 hours at ~ 75 ℃.
화학식 3Formula 3
화학식 4Formula 4
그리고, 상기 화학식 2로 표시되는 폴리아크릴로일클로라이드-g-폴리피롤은 상기 화학식 1로 표시되는 폴리아크릴로일피롤을 전기화학 중합하여 얻어지는 것임을 특징으로 한다.The polyacryloyl chloride-g-polypyrrole represented by Chemical Formula 2 may be obtained by electrochemical polymerization of the polyacryloylpyrrole represented by Chemical Formula 1.
도 1은 본 발명 실시예 1에 따라 얻어진 폴리아크릴로일 피롤의 적외선 흡수 스펙트럼이고,1 is an infrared absorption spectrum of a polyacryloyl pyrrole obtained according to Example 1 of the present invention,
도 2는 본 발명 실시예 2에 따라 얻어진 폴리아크릴로일 피롤의 적외선 흡수 스펙트럼이다.2 is an infrared absorption spectrum of polyacryloyl pyrrole obtained according to Example 2 of the present invention.
이와같은 본 발명을 더욱 상세하게 설명하면 다음과 같다.The present invention will be described in more detail as follows.
본 발명은 상기 화학식 1로 표시되는 폴리아크릴로일 피롤과 이로부터 얻어진 상기 화학식 2로 표시되는 폴리아크릴로일클로라이드-g-폴리피롤과 이들의 제조방법에 관한 것이다.The present invention relates to a polyacryloyl pyrrole represented by the formula (1), and a polyacryloyl chloride-g-polypyrrole represented by the formula (2) obtained therefrom and a method for producing the same.
본 발명에서 상기 화학식 1로 표시되는 폴리아크릴로일 피롤은 상기 화학식 3으로 표시되는 피롤염과 상기 화학식 4로 표시되는 아크릴로일 클로라이드로부터 제조된다.In the present invention, the polyacryloyl pyrrole represented by Chemical Formula 1 is prepared from the pyrrole salt represented by Chemical Formula 3 and the acryloyl chloride represented by Chemical Formula 4.
여기서, 화학식 3으로 표시되는 피롤염은 피롤과 포타슘 하이드라이드를 용매 존재 하에서 상온으로 1∼24시간 반응시켜 현탁액으로 얻을 수 있다.Here, the pyrrole salt represented by the formula (3) can be obtained as a suspension by reacting pyrrole and potassium hydride at room temperature for 1 to 24 hours in the presence of a solvent.
이와같이 얻어진 피롤염과 아크릴로일 클로라이드를 -20 내지 50℃에서 1 내지 24시간 동안 반응시킨 후, 여기에 개시제로서 AIBN을 넣고 55 내지 75℃에서 1 내지 24시간 동안 반응시키면 본 발명에서의 화학식 1로 표시되는 폴리아크릴로일피롤을 얻을 수 있다.The pyrrole salt and the acryloyl chloride thus obtained are reacted at -20 to 50 ° C for 1 to 24 hours, and then AIBN is added thereto as an initiator and reacted at 55 to 75 ° C for 1 to 24 hours. Polyacryloylpyrrole represented by can be obtained.
이의 구체적인 반응메카니즘은 다음 반응식 1과 같다.The specific reaction mechanism thereof is shown in Scheme 1 below.
이와같이 얻어진 폴리아크릴로일 피롤은 분자량이 1000 내지 500000이며, 피롤의 치환률이 1 내지 50%이다.The polyacryloyl pyrrole thus obtained has a molecular weight of 1000 to 500000 and a substitution rate of pyrrole of 1 to 50%.
한편, 본 발명에서 전도성 고분자의 단점을 개선하면서 복합체에 비해 전기전도도가 우수한 특성을 갖는 화학식 2로 표시되는 폴리아크릴로일 클로라이드-g-폴리피롤은 상기와 같이 얻어진 화학식 1로 표시되는 폴리아크릴로일 피롤로부터 제조되어진다.On the other hand, the polyacryloyl chloride-g-polypyrrole represented by the formula (2) having the characteristics of excellent electrical conductivity compared to the composite while improving the disadvantages of the conductive polymer in the present invention polyacryloyl represented by the formula (1) obtained as described above It is made from pyrrole.
구체적으로는 화학식 1로 표시되는 폴리아크릴로일 피롤을 아세토니트릴에 녹여 용해시킨 후, 백금 전극상에 스핀 코팅하여 3전극 셀을 사용하여 전기화학방법에 의해 제조한다. 구체적인 전기화학 중합조건으로는 용매로는 아세토니트릴 또는 디클로로메탄 등을 사용할 수 있고, 단량체로는 피롤을, 지지 전해질로는 Et4NBF4를 사용할 수 있고, 전위는 -1.0 내지 +1.0V, 중합시간은 1 내지 2시간인 것이 바람직하다.Specifically, the polyacryloyl pyrrole represented by the formula (1) is dissolved in acetonitrile and dissolved, followed by spin coating on a platinum electrode to prepare a electrochemical method using a three-electrode cell. As specific electrochemical polymerization conditions, acetonitrile or dichloromethane may be used as a solvent, pyrrole may be used as a monomer, and Et 4 NBF 4 may be used as a supporting electrolyte, and the potential is −1.0 to +1.0 V. It is preferable that time is 1 to 2 hours.
이와 같은 전기화학 중합을 거치면 짙은 갈색의 필름을 얻을 수 있는데, 이것이 화학식 2로 표시되는 폴리아크릴로일 클로라이드-g-폴리피롤이다. 얻어진 폴리아크릴로일 클로라이드-g-폴리피롤의 분자량은 50000 내지 300000인 것이 바람직하다.Through such electrochemical polymerization, a dark brown film is obtained, which is polyacryloyl chloride-g-polypyrrole represented by the formula (2). The molecular weight of the obtained polyacryloyl chloride-g-polypyrrole is preferably 50000 to 300000.
이와 같이 얻어진 폴리아크릴로일 클로라이드-g-폴리피롤은 한 구조로 인해 복합체에 비해서는 전기전도도가 우수하면서 유연한 특성을 갖게 된다.Thus obtained polyacryloyl chloride-g-polypyrrole has excellent electrical conductivity and flexible properties compared to the composite due to one structure.
이하, 본 발명을 실시예에 의거 상세히 설명하면 다음과 같은 바, 본 발명이 실시예에 의해 한정되는 것은 아니다.Hereinafter, the present invention will be described in detail with reference to Examples, but the present invention is not limited by the Examples.
실시예 1: 폴리아크릴로일 피롤의 제조Example 1 Preparation of Polyacryloyl Pyrrole
3구 플라스크에 질소를 흘려주면서 분말 형태의 포타슘 하이드라이드를 n-헥산으로 미네랄 오일을 제거한 후 넣고, 정제한 THF를 대기와의 접촉을 피하기 위하여 주사기를 이용하여 주입하였다. 마그네틱 바를 사용하여 상온에서 반응액을 교반하면서 새로 정제한 피롤을 당량비로 주입하고, 상온에서 4시간 동안 반응시켜 포타슘 피롤염을 합성하였다.Nitrogen was poured into the three-necked flask, and powdered potassium hydride was removed after removing mineral oil with n-hexane, and purified THF was injected by using a syringe to avoid contact with the atmosphere. Using a magnetic bar, while stirring the reaction solution at room temperature, newly purified pyrrole was injected in an equivalent ratio, and reacted at room temperature for 4 hours to synthesize potassium pyrrole salt.
합성한 포타슘 피롤 염에 새롭게 정제한 아크릴로일 클로라이드를 THF에 녹여서 적가 펀넬을 통해 30분에 걸쳐 천천히 적가하였다. 적가시 심한 발열을 피하기 위해 아이스 배쓰를 사용하여 0℃로 온도를 낮추어 적가하고, 적가 완료 후에 다시 상온에서 4시간 동안 반응시켜 아크릴로일 피롤을 합성하였다.The newly purified acryloyl chloride was dissolved in THF and slowly added dropwise to the synthesized potassium pyrrole salt over 30 minutes through a dropwise funnel. In order to avoid severe exotherm during dropping, a drop in temperature was lowered to 0 ° C. using an ice bath, followed by reaction at room temperature for 4 hours again to synthesize acryloyl pyrrole.
아크릴로일 피롤이 합성된 플라스크에 개시제인 AIBN을 THF에 녹여서 넣고, 70℃에서 8시간 동안 반응시켜 폴리아크릴로일 피롤을 합성하였다.AIBN, an initiator, was dissolved in THF in a flask prepared with acryloyl pyrrole and reacted at 70 ° C. for 8 hours to synthesize polyacryloyl pyrrole.
합성한 화합물은 갈색 분말이었으며, 치환된 피롤의 함량을 NMR의 면적비로측정한 결과 34%였다. 그리고, 분자량은 70000 이었다.The synthesized compound was a brown powder, and the content of substituted pyrrole was 34% as measured by the area ratio of NMR. And the molecular weight was 70000.
합성한 화합물의 적외선 흡수 스펙트럼은 도 1과 같다.The infrared absorption spectrum of the synthesized compound is shown in FIG. 1.
실시예 2: 폴리아크릴로일 피롤의 제조Example 2: Preparation of Polyacryloyl Pyrrole
상기 실시예 1과 같은 방법으로 폴리아크릴로일 피롤을 제조하되, 다만 합성시 반응시간을 2시간으로 하여 수행하였다. 얻어진 화합물은 갈색 분말이었으며, 치환된 피롤의 함량은 NMR의 면적비에 의해 측정한 결과 10%이었다. 그리고, 분자량은 40000 이었다.Polyacryloyl pyrrole was prepared in the same manner as in Example 1, except that the reaction time was 2 hours. The obtained compound was brown powder, and the content of substituted pyrrole was 10% as measured by the area ratio of NMR. And the molecular weight was 40000.
합성한 화합물의 적외선 흡수 스펙트럼은 도 2와 같다.The infrared absorption spectrum of the synthesized compound is shown in FIG. 2.
실시예 3: 폴리아크릴로일 클로라이드-g-폴리피롤의 제조Example 3: Preparation of Polyacryloyl Chloride-g-Polypyrrole
상기 실시예 1로부터 얻어진 폴리아크릴로일 피롤을 아세토니트릴에 녹여 용해시킨 후, 원형 백금 전극상에 스핀 코팅하여 3전극 셀을 사용해 전기화학 방법에 의해 폴리아크릴로일 클로라이드-g-폴리피롤을 제조하였다.The polyacryloyl pyrrole obtained in Example 1 was dissolved in acetonitrile and dissolved, followed by spin coating on a circular platinum electrode to prepare polyacryloyl chloride-g-polypyrrole by an electrochemical method using a three-electrode cell. .
이때, 전기화학 중합조건으로는 용매로는 아세토니트릴을, 단량체로는 피롤을, 지지 전해질로는 Et4NBF4를 사용하였고, 가해준 전위는 0.8V이고, 중합시간은 1시간이었다.In this case, acetonitrile was used as the solvent, pyrrole was used as the monomer, and Et4NBF4 was used as the supporting electrolyte. The potential applied was 0.8 V and the polymerization time was 1 hour.
결과적으로 짙은 갈색의 필름을 얻었으며, 그 분자량은 200000 이었다.As a result, a dark brown film was obtained with a molecular weight of 200000.
제조한 폴리아크릴로일 클로라이드-g-폴리피롤을 DSC(PERKIN ELMER 제품)를 사용하여 측정한 결과 녹는점은 209℃였다.The polyacryloyl chloride-g-polypyrrole prepared was measured using DSC (product of PERKIN ELMER), and the melting point was 209 ° C.
실시예 4: 폴리아크릴로일 클로라이드-g-폴리피롤의 제조Example 4 Preparation of Polyacryloyl Chloride-g-Polypyrrole
상기 실시예 3과 동일한 방법으로 폴리아크릴로일 클로라이드-g-폴리피롤을 제조하되, 다만 용매로서 디클로로메탄을 사용하였다.Polyacryloyl chloride-g-polypyrrole was prepared in the same manner as in Example 3, except dichloromethane was used as a solvent.
결과적으로 짙은 갈색의 필름을 얻었으며, 그 분자량은 240000이었다.As a result, a dark brown film was obtained, whose molecular weight was 240000.
제조한 폴리아크릴로일 클로라이드-g-폴리피롤을 DSC(PERKIN ELMER 제품)를 사용하여 측정한 결과 녹는점은 215℃였다.The polyacryloyl chloride-g-polypyrrole was measured using DSC (product of PERKIN ELMER) and the melting point was 215 ° C.
실시예 5: 폴리아크릴로일 클로라이드-g-폴리피롤의 제조Example 5 Preparation of Polyacryloyl Chloride-g-Polypyrrole
상기 실시예 3과 동일한 방법으로 폴리아크릴로일 클로라이드-g-폴리피롤을 제조하되, 다만 가해준 전위를 0.95V로 변경하였다.Polyacryloyl chloride-g-polypyrrole was prepared in the same manner as in Example 3, except that the applied potential was changed to 0.95V.
결과적으로 짙은 갈색의 필름을 얻었으며, 그 분자량은 300000 이었다.As a result, a dark brown film was obtained, which had a molecular weight of 300000.
제조한 폴리아크릴로일 클로라이드-g-폴리피롤을 DSC(PERKIN ELMER 제품)를 사용하여 측정한 결과 녹는점은 221℃였다.The polyacryloyl chloride-g-polypyrrole produced was measured using DSC (product of PERKIN ELMER) and the melting point was 221 ° C.
비교예 1: 폴리아크릴로일 클로라이드/폴리피롤의 제조Comparative Example 1: Preparation of Polyacryloyl Chloride / Polypyrrole
폴리아크릴로일 클로라이드(합성, 분자량 25000)를 아세토니트릴에 녹여 용해시킨 후, 원형 백금 전극상에 스핀 코팅하여 3전극 셀을 사용하여 전기화학 방법에 의해 폴리아크릴로일 클로라이드/폴리피롤을 제조하였다.Polyacryloyl chloride (synthetic, molecular weight 25000) was dissolved in acetonitrile and dissolved, followed by spin coating on a circular platinum electrode to prepare polyacryloyl chloride / polypyrrole by electrochemical method using a three-electrode cell.
전기화학 중합조건으로는 용매는 아세토니트릴을, 단량체로는 피롤을, 지지전해질로는 Et4NBF4를 사용하였고, 가해준 전위는 0.8V였고, 중합시간은 1시간이었다.As electrochemical polymerization conditions, acetonitrile was used as the solvent, pyrrole was used as the monomer, and Et 4 NBF 4 was used as the supporting electrolyte. The potential applied was 0.8 V and the polymerization time was 1 hour.
결과적으로 짙은 갈색의 필름을 얻었다.As a result, a dark brown film was obtained.
제조한 폴리아크릴로일 클로라이드/폴리피롤을 DSC(PERKIN ELMER 제품)를 사용하여 측정한 결과 녹는점은 181℃였다.The polyacryloyl chloride / polypyrrole produced was measured using DSC (product of PERKIN ELMER) and the melting point was 181 ° C.
비교예 2: 폴리아크릴로일 클로라이드/폴리피롤의 제조Comparative Example 2: Preparation of Polyacryloyl Chloride / Polypyrrole
상기 비교예 1과 동일한 방법으로 폴리아크릴로일 클로라이드/폴리피롤을 제조하되, 다만 용매로서 디클로로메탄을 사용하였다.Polyacryloyl chloride / polypyrrole was prepared in the same manner as in Comparative Example 1, except dichloromethane was used as a solvent.
결과적으로 짙은 갈색의 필름을 얻었다.As a result, a dark brown film was obtained.
제조한 폴리아크릴로일 클로라이드/폴리피롤을 DSC(PERKIN ELMER 제품)를 사용하여 측정한 결과 녹는점은 189℃였다.The polyacryloyl chloride / polypyrrole produced was measured using DSC (product of PERKIN ELMER), and the melting point was 189 ° C.
비교예 3: 폴리아크릴로일 클로라이드/폴리피롤의 제조Comparative Example 3: Preparation of Polyacryloyl Chloride / Polypyrrole
상기 비교예 1과 동일한 방법으로 폴리아크릴로일 클로라이드/폴리피롤을 제조하되, 다만 가해준 전위를 0.95V로 변경하였다.Polyacryloyl chloride / polypyrrole was prepared in the same manner as in Comparative Example 1, except that the applied potential was changed to 0.95V.
결과적으로 짙은 갈색의 필름을 얻었다.As a result, a dark brown film was obtained.
제조한 폴리아크릴로일 클로라이드/폴리피롤을 DSC(PERKIN ELMER 제품)를 사용하여 측정한 결과 녹는점은 193℃였다.The polyacryloyl chloride / polypyrrole produced was measured using DSC (product of PERKIN ELMER), and the melting point was 193 ° C.
실험예: 전기전도도의 측정Experimental Example: Measurement of Electrical Conductivity
상기 실시예로부터 얻어진 폴리아크릴로일 클로라이드-g-폴리피롤과 비교예로부터 얻어진 폴리아크릴로일 클로라이드/폴리피롤 필름의 전도도를 Keithly 2400 Sourcemeter(FLUKE사 제품)를 이용하여 4단자법으로 하여 측정하였다.The conductivity of the polyacryloyl chloride-g-polypyrrole obtained from the above example and the polyacryloyl chloride / polypyrrole film obtained from the comparative example was measured by a four-terminal method using a Keithly 2400 Sourcemeter (manufactured by FLUKE).
그 결과는 다음 표 1과 같다.The results are shown in Table 1 below.
상기 표 1의 결과로부터, 본 발명에서 얻어진 폴리아크릴로일 클로라이드-g-폴리피롤을 사용할 경우 종래 사용되던 복합체에 비하여 전기전도도가 더 큰 것을 알 수 있다.From the results of Table 1, it can be seen that when using the polyacryloyl chloride-g-polypyrrole obtained in the present invention, the electrical conductivity is larger than that of the conventional composite.
본 실험의 결과로부터 얻어진 폴리아크릴로일 클로라이드-g-폴리피롤을 사용할 경우 전도성 고분자와 비교해 볼 때 필름 형태로 얻을 수 있으므로 가공이 가능하고, 전도성 고분자의 문제점인 부서짐과 같은 단점을 해결할 수 있었다.When using the polyacryloyl chloride-g-polypyrrole obtained from the results of this experiment can be obtained in the form of a film compared to the conductive polymer can be processed, it was possible to solve the disadvantages such as breakage, a problem of the conductive polymer.
이상에서 상세히 설명한 바와 같이, 본 발명에 따라 얻어진 폴리아크릴로일 클로라이드-g-폴리피롤은 전도성 고분자의 단점을 개선하여 가공성, 유연성, 용해성이 우수하면서도 복합체에 비하여 전기전도도가 우수하여, 플라스틱 축전지, 스마트 윈도우, 전자기파 차폐재 등으로 유용하다.As described in detail above, the polyacryloyl chloride-g-polypyrrole obtained in accordance with the present invention improves the disadvantages of the conductive polymer and is excellent in processability, flexibility, and solubility, but also excellent in electrical conductivity compared to the composite, plastic storage battery, smart It is useful as a window, electromagnetic wave shielding material and the like.
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