KR100304054B1 - Making method of solubility polypyrrole to make of use mixed dofant - Google Patents
Making method of solubility polypyrrole to make of use mixed dofant Download PDFInfo
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- KR100304054B1 KR100304054B1 KR1019980041959A KR19980041959A KR100304054B1 KR 100304054 B1 KR100304054 B1 KR 100304054B1 KR 1019980041959 A KR1019980041959 A KR 1019980041959A KR 19980041959 A KR19980041959 A KR 19980041959A KR 100304054 B1 KR100304054 B1 KR 100304054B1
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- polypyrrole
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- dopant
- solubility
- dbsa
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- 229920000128 polypyrrole Polymers 0.000 title claims abstract description 21
- 238000000034 method Methods 0.000 title description 3
- 239000002019 doping agent Substances 0.000 claims abstract description 24
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims abstract description 12
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000004519 manufacturing process Methods 0.000 claims abstract description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 239000002245 particle Substances 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 239000003990 capacitor Substances 0.000 abstract description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract description 2
- 229910052782 aluminium Inorganic materials 0.000 abstract description 2
- 239000004020 conductor Substances 0.000 abstract description 2
- 229910052715 tantalum Inorganic materials 0.000 abstract description 2
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 abstract description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
- 239000003960 organic solvent Substances 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 239000012153 distilled water Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 239000002798 polar solvent Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- -1 carboxy1 Chemical group 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- FYAQQULBLMNGAH-UHFFFAOYSA-N hexane-1-sulfonic acid Chemical compound CCCCCCS(O)(=O)=O FYAQQULBLMNGAH-UHFFFAOYSA-N 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- WXHLLJAMBQLULT-UHFFFAOYSA-N 2-[[6-[4-(2-hydroxyethyl)piperazin-1-yl]-2-methylpyrimidin-4-yl]amino]-n-(2-methyl-6-sulfanylphenyl)-1,3-thiazole-5-carboxamide;hydrate Chemical compound O.C=1C(N2CCN(CCO)CC2)=NC(C)=NC=1NC(S1)=NC=C1C(=O)NC1=C(C)C=CC=C1S WXHLLJAMBQLULT-UHFFFAOYSA-N 0.000 description 1
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 238000005536 corrosion prevention Methods 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G9/00—Electrolytic capacitors, rectifiers, detectors, switching devices, light-sensitive or temperature-sensitive devices; Processes of their manufacture
- H01G9/004—Details
- H01G9/022—Electrolytes; Absorbents
- H01G9/025—Solid electrolytes
- H01G9/032—Inorganic semiconducting electrolytes, e.g. MnO2
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Electrochemistry (AREA)
- Engineering & Computer Science (AREA)
- Power Engineering (AREA)
- Inorganic Chemistry (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
Abstract
본 발명은 알루미늄 콘덴서나 탄탈콘덴서와 같은 콘덴서 제조시 전도체로 사용되는 폴리피롤에 있어서, 높은 용해성을 갖는 폴리피롤을 제조하기 위하여 긴사슬(CnH2n+1C6H5SO3H, n=8~12)의 DBSA (dodecyl benzen sulfonicacid) 0.1 mol과의 혼합 도판트를 피롤 0.4 mol과 반응시켜 가용성 폴리피롤을 제조하는 것을 특징으로 하는 혼합 도판트를 사용한 가용성 폴리피롤의 제조방법을 제공한다.In the present invention, in the polypyrrole used as a conductor when manufacturing a capacitor such as an aluminum capacitor or a tantalum capacitor, a long chain (C n H 2n + 1 C 6 H 5 SO 3 H, n = 8) is used to prepare polypyrrole having high solubility. It provides a method for producing a soluble polypyrrole using a mixed dopant, characterized in that to react the mixed dopant with 0.1 mol of dodecyl benzen sulfonicacid (DBSA ~ 12) with 0.4 mol of pyrrole.
Description
본 발명은 알루미늄 콘덴서나 탄탈콘덴서와 같은 콘덴서 제조시 전도체로 사용되는 혼합 도판트를 사용한 가용성 폴리피롤의 제조방법에 관한 것이다.The present invention relates to a method for producing soluble polypyrrole using a mixed dopant used as a conductor in the manufacture of a capacitor such as an aluminum capacitor or tantalum capacitor.
폴리피롤은 정전기 방지, 전자기파 차폐, 축전지, photoelectrochemical 전지, electrochromic display, 부식방지, resisitive heating, cableshielding, microwave absorbor, 온도센서, 충격센서, 화학적 센서 등에 이용되고, 특히 높은 전기 전도도와 열적 안정성, 저렴한 단가, 고주파 영역에서의 이상적인 저임피던스 가능, 우수한 노이즈(noise) 흡수성, 넓은 온도, 주파수 영역에서의 안정한 정전 용량 때문에 고체 전해 콘덴서의 전해질층으로 사용된다.Polypyrrole is used in anti-static, electromagnetic shielding, battery, photoelectrochemical cell, electrochromic display, corrosion prevention, resisitive heating, cableshielding, microwave absorbor, temperature sensor, shock sensor, chemical sensor, etc., especially high electrical conductivity and thermal stability, low cost, It is used as an electrolyte layer of solid electrolytic capacitors because of its ideal low impedance in the high frequency region, excellent noise absorption, wide temperature, and stable capacitance in the frequency region.
기존의 폴리피롤의 제조방법은 500 mol 증류수속에 0.30 mol 피롤과 0.15 mol DBSA(dodecyl benzen sulfonic acid)를 혼합하고 섞는다. 별도로 0.06 mol(NH4)2S2O8를 100 mol 증류수에 혼합하여 섞는다.The conventional method for producing polypyrrole is mixed with 0.30 mol pyrrole and 0.15 mol DBSA (dodecyl benzen sulfonic acid) in 500 mol distilled water. Separately, mix and mix 0.06 mol (NH 4 ) 2 S 2 O 8 in 100 mol distilled water.
0°C에서 24시간 반응시키고 메탄올, 아세톤, 증류수로 세척후 여과한다. 여과된 분말을 30°C에서 12시간 진공오븐에서 건조하여 폴리피롤 분말을 제조한다.After 24 hours of reaction at 0 ° C. and washed with methanol, acetone, distilled water and filtered. The filtered powder is dried in a vacuum oven at 30 ° C. for 12 hours to prepare a polypyrrole powder.
DBSA(dodecyl benzene sulfonic acid)를 도판트를 사용하여 m-cresol, chloroform, THF(tetrahydrofuran), DMF(dimethylformamide)의 일부 유기용매에 용해가 가능한 폴리피롤을 제조하였다.Dodecyl benzene sulfonic acid (DBSA) was used as a dopant to prepare polypyrrole that can be dissolved in some organic solvents of m-cresol, chloroform, THF (tetrahydrofuran), and DMF (dimethylformamide).
이러한 긴 사슬의 DBSA만을 도판트로 사용하였기 때문에 도판트와 용매에 대한 상호작용을 고려하지 않은 결과가 되어 m-cresol, o-chlorophenol, chloroform, dichloromethane, THF, DMSO, NMP, DMF, trifluoroethanol, trifluoroacetic acid, benzyl alchol와 같은 일반적인 유기용매에 대한 용해도가 매우 낮고 가공성이 떨어지는 단점이 있었다.Since only the long chain DBSA was used as the dopant, the interaction between the dopant and the solvent was not considered, resulting in m-cresol, o-chlorophenol, chloroform, dichloromethane, THF, DMSO, NMP, DMF, trifluoroethanol, and trifluoroacetic acid. However, the solubility in general organic solvents such as benzyl alchol was very low and the processability was poor.
또한, 기존 방법에 의한 DBSA만으로 도핑된 폴리피롤은 극성 정도가 적은 m-cresol, 극성인 THF, DMF의 한정된 일부 유기용매에 낮은 유기용매에 낮은 용해성 (3 wt%/vol 미만)을 갖으며 비극성인 chloroform 용매에 용해시 1g의 DBSA을 또 첨가하여야만 용해성을 보여주는 문제점을 가졌다.In addition, polypyrrole doped with DBSA by conventional methods has low solubility (less than 3 wt% / vol) in non-polar m-cresol, polar THF, and some limited organic solvents of DMF and low polarity. When dissolved in chloroform solvent, 1g of DBSA should be added to show solubility.
본 발명은 전술한 바와 같은 문제점을 해결하기 위하여 안출된 것으로, 본 발명은 일반적인 유기용매에 대해 높은 용해성을 가지는 폴리피롤을 제조하기 위한 것이다.The present invention has been made to solve the above problems, the present invention is to produce a polypyrrole having a high solubility in a general organic solvent.
본 발명은 전술한 목적을 달성하기 위한 것으로서, 본 발명은 긴 사슬 (CnH2n+1C6H5SO3H, n=8~12)의 DBSA(dodecyl benzen sulfonic acid 0.1 mol 와 큰 입자크기의 극성을 갖는 도판트(alkoxy, carboxyl, sulfonyl, hydroxy1) 0.1 mol과의 혼합도판트를 피롤 0.4 mol과 반응시켜 가용성 폴리피롤을 제조하는 것을 특징으로 하는 혼합도판트를 사용한 가용성 폴리피롤의 제조방법을 제공한다.The present invention is to achieve the above object, the present invention is a long chain (C n H 2n + 1 C 6 H 5 SO 3 H, n = 8 ~ 12) DBSA (dodecyl benzen sulfonic acid 0.1 mol and large particles) A method for preparing soluble polypyrrole using a mixed dopant is prepared by reacting a mixed dopant with 0.1 mol of dopant (alkoxy, carboxyl, sulfonyl, hydroxy1) having polarity of size with 0.4 mol of pyrrole. to provide.
도 1은 다양한 유기용매내에서 용해된 본 발명에 의한 극성작용기인 DES와 DBSA의 혼합 도판트로 도핑된 폴리피롤의 UV/Vis.-NIR 스펙트럼.1 is a UV / Vis.-NIR spectrum of polypyrrole doped with a mixed dopant of DES and DBSA, a polar functional group according to the invention, dissolved in various organic solvents.
이하, 첨부된 도면을 참조하여 본 발명의 구성과 작용을 설명한다.Hereinafter, with reference to the accompanying drawings will be described the configuration and operation of the present invention.
도 1은 다양한 유기 용매내에서 용해된 본 발명에 의한 극성 작용기인 DES와 DBSA의 혼합 도판트로 도핑된 폴리피롤의 UN/Vis-NIR 스펙트럼이다.1 is a UN / Vis-NIR spectrum of polypyrrole doped with a mixed dopant of DES and DBSA, a polar functional group according to the invention, dissolved in various organic solvents.
상기 도 1에서 알수 있듯이, UN/Vis.-NIR 스펙트럼의 결과에서도 극성 용매에 대해 근 적외선 영역에서의 강한 흡수 피크를 보여주고 있다.As can be seen in Figure 1, the results of the UN / Vis.-NIR spectrum also shows a strong absorption peak in the near infrared region for the polar solvent.
긴 사슬(CnH2n+1C6H5SO3H, n=8~12)의 DBSA(dodecyl benzen sulfonic acid) 0.1 mol와 큰 입자크기의 극성을 갖는 도판트(alkoxy(알콕시), carboxy1(카보닐), sulfony1(설폰닐), hydroxyl(수산화기)) 0.1 mol과의 혼합도판트를 피롤 0.4 mol과 반응시켜 가용성 폴리피롤을 제조한다.0.1 mol of dodecyl benzen sulfonic acid (DBSA) of long chains (C n H 2n + 1 C 6 H 5 SO 3 H, n = 8-12) and a polar dopant having a large particle size (alkoxy, alkoxy) Soluble polypyrrole is prepared by reacting a mixed dopant with 0.1 mol (carbonyl), sulfonyl (sulfonyl), hydroxyl (hydroxyl group)) with 0.4 mol of pyrrole.
상기의 방법에 의한 일실시예를 설명하면 다음과 같다.An embodiment according to the above method will be described.
증류수 80 ml속에 0.4 mol의 피롤과 0.05 mol의 DBSA를 넣어 잘 섞은 후 별로도 20 ml 증류수와 0.05 mol의 DBSA와 0.1 mol의 극성을 갖는 도판트(alkoxy, carboxyl, sulfonyl, hydroxyl 등)를 산화제인 (NH4)2S2O80.08 mol과 혼합하여 섞는다.After mixing 0.4 mol pyrrole and 0.05 mol DBSA in 80 ml of distilled water, mix 20 ml distilled water with 0.05 mol DBSA and 0.1 mol polar dopant (alkoxy, carboxyl, sulfonyl, hydroxyl, etc.). (NH 4 ) 2 S 2 O 8 Mix with 0.08 mol and mix.
0°C에서 20시간 반응시키고 증류수 또는 0.1 M의 극성을 갖는 도판트 (alkoxy, carboxyl, sulfonyl, hydroxyl 등) 수용액으로 세척하여 여과한다. 여기서 얻어진 분말을 24시간 진공 건조 라인에서 건조시켜 폴리피롤 분말을 얻는다.The reaction is carried out at 0 ° C. for 20 hours and filtered by washing with distilled water or aqueous dopant (alkoxy, carboxyl, sulfonyl, hydroxyl, etc.) having a polarity of 0.1 M. The powder obtained here is dried in a vacuum drying line for 24 hours to obtain polypyrrole powder.
본 발명에 의한 극성 작용기(alkoxy, carboxy1, sulfonyl, hydroxyl)를 갖고 있는 도판트, sulfosalichlic acid(SSA), diethysulfate(DES), sodium salt 4-hydoxy hexane sulfonate(SHES)을 DBSA와 함께 도판트로 사용하여 합성된 폴리피롤을 여러 가지 유기용매에 녹여 용해도를 측정하여 표 1에 나타내었다.Dopant having a polar functional group (alkoxy, carboxy1, sulfonyl, hydroxyl) according to the present invention, sulfosalichlic acid (SSA), diethysulfate (DES), sodium salt 4-hydoxy hexane sulfonate (SHES) using a DBSA with a dopant The synthesized polypyrrole was dissolved in various organic solvents and the solubility was measured.
[표 1] 기존 방식에 의한 DBSA로 도핑된 폴리피롤과 본 발명에 의한 혼합도판트로 도핑된 폴리피롤의 용해도(wt % vol.)Table 1 Solubility of polypyrrole doped with DBSA according to the conventional method and polypyrrole doped with mixed dopant according to the present invention (wt% vol.)
※ sulfosalicylic acid; SSA, diethylsulfate; DESSulfosalicylic acid; SSA, diethylsulfate; DES
sodium salt 4-hydoxy hexane sulfonate; SHHSsodium salt 4-hydoxy hexane sulfonate; SHHS
DBSA만을 도판트로 사용하였을 경우에는 DBSA의 낮은 극성으로 인하여 대부분의 극성 용매에 대해 친화성을 보이지 않아 용해도가 떨어지는 단점을 가지고 있다. 그러나, 극성을 갖는 도판트(alkoxy, carboxyl, sulfonyl, hydroxyl 등)을 첨가하면 대부분의 극성 용매에 대해 친화성이 증가하여 일반적인 유기용매에 대한 용해성이 증가된다.When only the DBSA is used as a dopant, due to the low polarity of the DBSA, there is a disadvantage in that the solubility is poor because it does not show affinity for most polar solvents. However, the addition of polar dopants (alkoxy, carboxyl, sulfonyl, hydroxyl, etc.) increases the affinity for most polar solvents, increasing the solubility in common organic solvents.
전술한 바와 같은 본 발명의 효과는 긴 사슬과 큰 입자크기의 극성 도판트를 혼합하여 사용하면 일반적인 유기용매(m-cresol, chloroform, dichlorform, NMP, DMSO, THF, DMF, benzylalcohol, trifluoroaethanol 등)에 대해 용해성을 향상시킬 수 있다.As described above, the effect of the present invention is that when a long chain and a large particle size polar dopant are mixed and used in general organic solvents (m-cresol, chloroform, dichlorform, NMP, DMSO, THF, DMF, benzylalcohol, trifluoroaethanol, etc.) Solubility can be improved.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20030000642A (en) * | 2001-06-26 | 2003-01-06 | 파츠닉(주) | Electrolyte layer forming method tantalum capacitor |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20020088976A (en) * | 2001-05-22 | 2002-11-29 | 파츠닉(주) | Making method of solubility polypyrrole having a high electric conductivity |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20030000642A (en) * | 2001-06-26 | 2003-01-06 | 파츠닉(주) | Electrolyte layer forming method tantalum capacitor |
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| KR20000025050A (en) | 2000-05-06 |
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