CN105237764A - Method for preparing poly-o-phenylenediamine microspheres by taking hydrogen peroxide as oxidizing agent - Google Patents
Method for preparing poly-o-phenylenediamine microspheres by taking hydrogen peroxide as oxidizing agent Download PDFInfo
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- CN105237764A CN105237764A CN201510723375.5A CN201510723375A CN105237764A CN 105237764 A CN105237764 A CN 105237764A CN 201510723375 A CN201510723375 A CN 201510723375A CN 105237764 A CN105237764 A CN 105237764A
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- phenylenediamine
- hydrogen peroxide
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- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 title claims abstract description 73
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 title claims abstract description 66
- 238000000034 method Methods 0.000 title claims abstract description 20
- 239000004005 microsphere Substances 0.000 title abstract description 5
- 239000007800 oxidant agent Substances 0.000 title abstract description 3
- 238000002360 preparation method Methods 0.000 claims abstract description 29
- 239000008367 deionised water Substances 0.000 claims abstract description 18
- 229910021641 deionized water Inorganic materials 0.000 claims abstract description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 18
- NLQWLEKKDYTBIR-UHFFFAOYSA-N benzene-1,2-diamine;hydrogen peroxide Chemical compound OO.NC1=CC=CC=C1N NLQWLEKKDYTBIR-UHFFFAOYSA-N 0.000 claims abstract description 5
- 230000009514 concussion Effects 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 7
- 239000005030 aluminium foil Substances 0.000 claims description 4
- 238000007789 sealing Methods 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000000243 solution Substances 0.000 abstract description 19
- 239000007864 aqueous solution Substances 0.000 abstract description 2
- 238000005303 weighing Methods 0.000 abstract description 2
- 239000007853 buffer solution Substances 0.000 abstract 4
- 239000000203 mixture Substances 0.000 abstract 2
- 238000005516 engineering process Methods 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 229920002334 Spandex Polymers 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 239000004759 spandex Substances 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000005611 electricity Effects 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 235000000509 Chenopodium ambrosioides Nutrition 0.000 description 1
- 244000098897 Chenopodium botrys Species 0.000 description 1
- 235000005490 Chenopodium botrys Nutrition 0.000 description 1
- 108010001336 Horseradish Peroxidase Proteins 0.000 description 1
- 244000000231 Sesamum indicum Species 0.000 description 1
- 235000003434 Sesamum indicum Nutrition 0.000 description 1
- DPDMMXDBJGCCQC-UHFFFAOYSA-N [Na].[Cl] Chemical compound [Na].[Cl] DPDMMXDBJGCCQC-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000002322 conducting polymer Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
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- Cosmetics (AREA)
- Manufacturing Of Micro-Capsules (AREA)
Abstract
The invention discloses a method for preparing poly-o-phenylenediamine microspheres by taking hydrogen peroxide as an oxidizing agent. The method comprises the following steps: I, preparation of a PBS buffer solution: preparing the PBS buffer solution, wherein the concentration of the solution is 40-50 mmol/L and the pH value is 7.0-7.5; II, preparation of an o-phenylenediamine solution: weighing out and dissolving 10-20 mg of o-phenylenediamine in 1-2 mL of the PBS buffer solution prepared in the step I; III, preparation of a hydrogen peroxide solution: adding 1-2 mL of the hydrogen peroxide solution into a container, then adding 2-4 mL of deionized water into the container, and vibrating and shaking the container to make the mixture in the container uniform; and IV, preparation of a hydrogen peroxide-o-phenylenediamine solution: adding the PBS buffer solution, the o-phenylenediamine solution and the hydrogen peroxide aqueous solution into the container in a volume ratio of 1 : 1 : (1-8), vibrating and shaking the container to make the mixture in the container uniform, and placing the container and leaving the container overnight. The method disclosed by the invention synthesizes poly-o-phenylenediamine microspheres by adopting a one-step method, so that the method is simple in step and convenient to operate, and the grain sizes and shapes of the poly-o-phenylenediamine microspheres are controlled by changing the processing conditions.
Description
Technical field
The invention belongs to field of polymer material preparing technology, relate to a kind of preparation method of poly-o-phenylenediamine microballoon.
Background technology
The structure of material and pattern have very important impact, so the polymer microsphere structure with different-shape causes the great interest of people (KawaguchiH, Prog.Polym.Sci., 2000,25:1171) for their performance.Rigid structure very difficult dissolving (HiguchiM, ImodaD, HiraoToshikazu.Adv.Mater., 1996,29:8277) in the common solvents such as methyl alcohol, acetonitrile, tetrahydrofuran (THF) that poly-o-phenylenediamine is special.Satisfactory stability makes its have a wide range of applications in the field such as bio-sensing, micro-touch reaction, antistatic layer, battery shielding material (LiD, HuangJX, RichardBK.AccChemRes, 2009142; 135-145).
Receive much concern because poly-o-phenylenediamine has good electricity, optics and redox characteristic always, have wide prospect in fields such as material, the energy, electromagnetic shieldings.Have electric conductive polymer since MacDiarmid in 1984 is obtained by O-Phenylene Diamine monomer in acid condition, poly-o-phenylenediamine has become one of the fastest conductive polymers of present progress.Reason is that poly-o-phenylenediamine has following tempting unique advantage: 1, raw material is easy to get, and synthesis is simple; 2, there is excellent microwave absorption performance, chemical property, chemical stability and optical property; 3, unique doping phenomenon; 4, high specific conductivity; 5, good environmental stability (ComposTLA is had, KerstingDF, FerreiraCA.Chemicalsynthesisofpolyanilineusingsulphanili cacidasdopantagentintothereactionalmedium [J], SurfaceandCoatingsTechnology, 1999,122:3-5., 2; Zhang Qinghua, Wang Xianhong, Jing Xiabin. the synthesis of poly-o-phenylenediamine and spectral response curve [J] thereof, chemistry world, 2001,5:242-244).Poly-o-phenylenediamine is considered to the conducting polymer composite being hopeful most to be applied in practice.To conduct electricity material based on poly-o-phenylenediamine, developing many new technologies at present, such as electromangnetic spectrum, antistatic technology, APollution prevention technology for ships, stealthy technique, overall plastic anti-corrosion of metal technology, solar cell, electrochromism, sensor element, secondary battery material, catalytic material and impregnating material (AmbrosiA, MorrinA, SmythMR, etal.AnalyticaChimicaActa [J] .2008, 609:37-43BrazdziuvieneK, JureviciuteI, MalinauskasA.ElectrochimActa [J] .2007, 53:785-791).
At present, more researchist finds that O-Phenylene Diamine is difficult to be oxidized to poly-o-phenylenediamine at normal temperatures, and major part is all by realizing in the form of catalyst forming poly-o-phenylenediamine micella or microballoon to the oxidation of O-Phenylene Diamine.As document (1) Synth.Met., 1997,84; The people such as 99-100, Sun obtain poly-o-phenylenediamine with iron ion catalyzing hydrogen peroxide oxidation O-Phenylene Diamine; Document (2) J.Am.Chem.Soc., 1999,121, the people such as 71-78, Liu obtain poly-o-phenylenediamine with horseradish peroxidase catalyses hydrogen peroxide oxidation O-Phenylene Diamine, document (3) J.Am.Chem.Soc., 2009, the people such as 131,12528-12529, Surwade utilize hydrogen peroxide oxidation O-Phenylene Diamine to obtain poly-o-phenylenediamine in the aqueous solution of sodium-chlor.These methods can obtain poly-o-phenylenediamine, but still can not realize single stage method hydrogen peroxide direct oxidation O-Phenylene Diamine at normal temperatures and pressures obtains the object of poly-o-phenylenediamine, and particle diameter and pattern all can not get effective control.
Summary of the invention
The object of this invention is to provide a kind of take hydrogen peroxide as the method that poly-o-phenylenediamine microballoon prepared by oxygenant, adopt one-step synthesis method poly-o-phenylenediamine microballoon, step is simple, easy to operate, can change processing conditions to control poly-o-phenylenediamine microspherulite diameter and pattern.
The object of the invention is to be achieved through the following technical solutions:
A kind of take hydrogen peroxide as the method that poly-o-phenylenediamine microballoon prepared by oxygenant, first o-phenylenediamine solution is added in PBS buffered soln, then be that oxygenant directly makes O-Phenylene Diamine in-situ polymerization with hydrogen peroxide, concussion shakes up and can obtain the poly-o-phenylenediamine of particle diameter and morphology controllable after leaving standstill.Concrete technology step is as follows:
One, the preparation of PBS buffered soln: take 2.9 ~ 3.0gNa
2hPO
4with 0.029 ~ 0.030gNaH
2pO
4be dissolved in 180 ~ 200mL deionized water, compound concentration be 40 ~ 50mmol/L, PBS buffered soln that pH value is 7.0 ~ 7.5;
Two, the preparation of o-phenylenediamine solution: take 10 ~ 20mg O-Phenylene Diamine and be dissolved in the PBS buffered soln of 1 ~ 2mL step one preparation;
Three, the preparation of superoxol; Be added in container by 1 ~ 2mL superoxol, then in container, add 2 ~ 4mL deionized water, concussion shakes up;
Four, the preparation of hydrogen peroxide-o-phenylenediamine solution: be PBS buffered soln, the o-phenylenediamine solution of step 2 preparation and the aqueous hydrogen peroxide solution of step 3 preparation that 1:1:1 ~ 8 add step one and prepare according to volume ratio in a reservoir, concussion shakes up and places and spends the night.
In step one of the present invention, the preparation steps of described PBS buffered soln is as follows: weighing 2.9 ~ 3.0gNa careful on precision balance
2hPO
4with 0.029 ~ 0.030gNaH
2pO
4, join in the vessel containing 180 ~ 200mL deionized water, shake in Ultrasonic Cleaners and shake up, make it dissolve completely.Recording its pH value with pH meter is 7.0 ~ 7.5, and concentration is 40 ~ 50mmol/L.
In step 2 of the present invention, the preparation steps of described o-phenylenediamine solution is as follows: precision balance weighs accurately 10 ~ 20mg O-Phenylene Diamine and be dissolved in the PBS buffered soln of 1 ~ 2mL step one preparation, in Ultrasonic Cleaners, concussion shakes up and makes it all dissolve, to be dissolved completely after keep in Dark Place with aluminium-foil paper sealing.
In step 3 of the present invention, the preparation steps of described superoxol is as follows: select commercially available AR rank hydrogen peroxide agent, measure 1 ~ 2mL superoxol and be added in vessel, then in vessel, add 2 ~ 4mL deionized water with liquid-transfering gun, concussion shakes up, and keeps in Dark Place with aluminium-foil paper sealing.
In step 4 of the present invention, the preparation steps of described hydrogen peroxide-o-phenylenediamine solution is as follows: measure 1mLPBS buffered soln, 1mL o-phenylenediamine solution, 1 ~ 8mL superoxol with liquid-transfering gun, slight concussion shakes up, and is placed in shady and cool dry place 12 ~ 24 hours.
In the present invention, the gloomy liquid-transfering gun of French gill is adopted to carry out measuring of solvent; Plum Teller-Tuo benefit ten thousand/precision balance is adopted to be used for taking of medicine; Plum Teller-Tuo benefit SevenCompact series pH meter is adopted to be used for the regulation and control of pH; IKAVORTEX vibrator is adopted to be used for the dissolving of solute; Adopt Ningbo new sesame biotechnology Ultrasonic Cleaners to be used for solution to dissolve completely; Adopt German Lycra DMi8 type fluorescence inverted microscope for the morphology observation of microballoon.
Effect of the present invention and advantage as follows:
1, one-step synthesis method poly-o-phenylenediamine microballoon, step is simple, operates more convenient.
What 2, the pattern of poly-o-phenylenediamine microballoon and particle diameter all controlled is fine.
3, this oxidizing reaction does not need very harsh condition, does not need to carry out anhydrous and oxygen-free operation, does not need other additional oxidant or catalyzer.
Accompanying drawing explanation
Fig. 1 is poly-o-phenylenediamine microballoon design sketch under German Lycra DMi8 type fluorescence inverted microscope prepared by embodiment 1;
Fig. 2 is that poly-o-phenylenediamine microballoon multiple under German Lycra DMi8 type fluorescence inverted microscope prepared by embodiment 1 amplifies rear design sketch;
Fig. 3 is that poly-o-phenylenediamine microballoon multiple under German Lycra DMi8 type fluorescence inverted microscope prepared by Fig. 2 amplifies rear grain size distribution.
Embodiment
Below in conjunction with accompanying drawing, technical scheme of the present invention is further described; but be not limited thereto; everyly technical solution of the present invention modified or equivalent to replace, and not departing from the spirit and scope of technical solution of the present invention, all should be encompassed in protection scope of the present invention.
Embodiment 1:
Take 2.9016gNa
2hPO
4and 0.0296gNaH
2pO
4to be dissolved in compound concentration in 200mL deionized water be the pH value of 50mmol/L be 7.4 PBS buffered soln; Taking 10mg O-Phenylene Diamine is dissolved in 1mLPBS buffered soln (50mmol/L, pH value is 7.4); Be added in container by 5mL superoxol, then in container, add 10mL deionized water, concussion shakes up; Adding pH value in a reservoir is respectively the PBS buffered soln of 7.4, the O-Phenylene Diamine prepared and each 1mL of aqueous hydrogen peroxide solution, and concussion shakes up and places spends the night.
The poly-o-phenylenediamine microballoon prepared of the present embodiment under German Lycra DMi8 type fluorescence inverted microscope design sketch as shown in Figure 1, after multiple amplifies, design sketch as shown in Figure 2.As shown in Figure 3, the poly-o-phenylenediamine microspherulite diameter that prepared by the present embodiment is about 11.5 μm.
Embodiment 2:
Take 2.9016gNa
2hPO
4and 0.0296gNaH
2pO
4to be dissolved in compound concentration in 200mL deionized water be the pH value of 50mmol/L be 7.4 PBS buffered soln; Taking 10mg O-Phenylene Diamine is dissolved in 1mLPBS buffered soln (50mmol/L, pH value is 7.4); Be added in container by 5mL superoxol, then in container, add 10mL deionized water, concussion shakes up; Add PBS buffered soln 1mL, o-phenylenediamine solution 1mL, aqueous hydrogen peroxide solution 2mL that pH value is 7.4 in a reservoir respectively, concussion shakes up and places spends the night.
Embodiment 3:
Take 2.9016gNa
2hPO
4and 0.0296gNaH
2pO
4to be dissolved in compound concentration in 200mL deionized water be the pH value of 50mmol/L be 7.4 PBS buffered soln; Taking 10mg O-Phenylene Diamine is dissolved in 1mLPBS buffered soln (50mmol/L, pH value is 7.4); Be added in container by 5mL superoxol, then in container, add 10mL deionized water, concussion shakes up; Add PBS buffered soln 1mL, o-phenylenediamine solution 1mL, aqueous hydrogen peroxide solution 4mL that pH value is 7.4 in a reservoir respectively, concussion shakes up and places spends the night.
Embodiment 4:
Take 2.9016gNa
2hPO
4and 0.0296gNaH
2pO
4to be dissolved in compound concentration in 200mL deionized water be the pH value of 50mmol/L be 7.4 PBS buffered soln; Taking 10mg O-Phenylene Diamine is dissolved in 1mLPBS buffered soln (50mmol/L, pH value is 7.4); Be added in container by 5mL superoxol, then in container, add 10mL deionized water, concussion shakes up; Add PBS buffered soln 1mL, o-phenylenediamine solution 1mL, aqueous hydrogen peroxide solution 8mL that pH value is 7.4 in a reservoir respectively, concussion shakes up and places spends the night.
Embodiment 5:
Take 2.9016gNa
2hPO
4and 0.0296gNaH
2pO
4to be dissolved in compound concentration in 200mL deionized water be the pH value of 50mmol/L be 7.4 PBS buffered soln; Taking 10mg O-Phenylene Diamine is dissolved in 1mLPBS buffered soln (50mmol/L, pH value is 7.4); Be added in container by 5mL superoxol, then in container, add 10mL deionized water, concussion shakes up; Add PBS buffered soln 1mL, o-phenylenediamine solution 1mL, aqueous hydrogen peroxide solution 10mL that pH value is 7.4 in a reservoir respectively, concussion shakes up and places spends the night.
Claims (7)
1. be the method that poly-o-phenylenediamine microballoon prepared by oxygenant with hydrogen peroxide, it is characterized in that described method steps is as follows:
One, the preparation of PBS buffered soln: the PBS buffered soln that compound concentration is 40 ~ 50mmol/L, pH value is 7.0 ~ 7.5;
Two, the preparation of o-phenylenediamine solution: take 10 ~ 20mg O-Phenylene Diamine and be dissolved in the PBS buffered soln of 1 ~ 2mL step one preparation;
Three, the preparation of superoxol; Be added in container by 1 ~ 2mL superoxol, then in container, add 2 ~ 4mL deionized water, concussion shakes up;
Four, the preparation of hydrogen peroxide-o-phenylenediamine solution: be PBS buffered soln, the o-phenylenediamine solution of step 2 preparation and the aqueous hydrogen peroxide solution of step 3 preparation that 1:1:1 ~ 8 add step one and prepare according to volume ratio in a reservoir, concussion shakes up and places and spends the night.
2. according to claim 1 is the method that poly-o-phenylenediamine microballoon prepared by oxygenant with hydrogen peroxide, it is characterized in that the preparation steps of described PBS buffered soln is as follows: weigh 2.9 ~ 3.0gNa
2hPO
4with 0.029 ~ 0.030gNaH
2pO
4join in the vessel containing 180 ~ 200mL deionized water, shake in Ultrasonic Cleaners and shake up, make it dissolve completely.
3. according to claim 1 is the method that poly-o-phenylenediamine microballoon prepared by oxygenant with hydrogen peroxide, and it is characterized in that the concentration of described PBS buffered soln is 50mmol/L, pH value is 7.4.
4. according to claim 1 take hydrogen peroxide as the method that poly-o-phenylenediamine microballoon prepared by oxygenant, it is characterized in that the preparation steps of described o-phenylenediamine solution is as follows: weigh 10 ~ 20mg O-Phenylene Diamine and be dissolved in the PBS buffered soln of 1 ~ 2mL step one preparation, in Ultrasonic Cleaners, concussion shakes up and makes it all dissolve, to be dissolved completely after keep in Dark Place with aluminium-foil paper sealing.
5. according to claim 1 take hydrogen peroxide as the method that poly-o-phenylenediamine microballoon prepared by oxygenant, it is characterized in that the preparation steps of described superoxol is as follows: measure 1 ~ 2mL superoxol with liquid-transfering gun and be added in vessel, then in vessel, 2 ~ 4mL deionized water is added, concussion shakes up, and keeps in Dark Place with aluminium-foil paper sealing.
6. be the method that poly-o-phenylenediamine microballoon prepared by oxygenant with hydrogen peroxide according to claim 1 or 5, it is characterized in that described hydrogen peroxide is AR rank hydrogen peroxide agent.
7. according to claim 1 take hydrogen peroxide as the method that poly-o-phenylenediamine microballoon prepared by oxygenant, it is characterized in that the preparation steps of described hydrogen peroxide-o-phenylenediamine solution is as follows: measure 1mLPBS buffered soln, 1mL o-phenylenediamine solution, 1 ~ 8mL superoxol with liquid-transfering gun, concussion shakes up, and is placed in shady and cool dry place 12 ~ 24 hours.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110105567A (en) * | 2019-06-12 | 2019-08-09 | 黄淮学院 | Poly-o-phenylenediamine derivative and its application |
| CN113797979A (en) * | 2021-09-15 | 2021-12-17 | 中国科学院长春应用化学研究所 | Modified nano particle, preparation method and application thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5792830A (en) * | 1996-12-09 | 1998-08-11 | The Dow Chemical Company | Process for preparing polyaniline |
| CN104098768A (en) * | 2014-06-26 | 2014-10-15 | 上海师范大学 | Method for preparing chirality polyaniline under cyclodextrin induction and biocatalysis in DBSA (dodecylbenzene sulfonic acid) micellar system |
-
2015
- 2015-10-29 CN CN201510723375.5A patent/CN105237764B/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5792830A (en) * | 1996-12-09 | 1998-08-11 | The Dow Chemical Company | Process for preparing polyaniline |
| CN104098768A (en) * | 2014-06-26 | 2014-10-15 | 上海师范大学 | Method for preparing chirality polyaniline under cyclodextrin induction and biocatalysis in DBSA (dodecylbenzene sulfonic acid) micellar system |
Non-Patent Citations (2)
| Title |
|---|
| HAIFENG LIU ET AL: "Enthalpy change and mechanism of oxidation of o-phenylenediamine by hydrogen peroxide catalyzed by horseradish peroxidase", 《THERMOCHIMICA ACTA》 * |
| SUMEDH P. SURWADE ET AL: "Catalyst-Free Synthesis of Oligoanilines and Polyaniline Nanofibers Using H2O2", 《JOURNAL OF AMERICAN CHEMICAL SOCIETY》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110105567A (en) * | 2019-06-12 | 2019-08-09 | 黄淮学院 | Poly-o-phenylenediamine derivative and its application |
| CN110105567B (en) * | 2019-06-12 | 2021-09-03 | 黄淮学院 | Poly-o-phenylenediamine derivative and application thereof |
| CN113797979A (en) * | 2021-09-15 | 2021-12-17 | 中国科学院长春应用化学研究所 | Modified nano particle, preparation method and application thereof |
| CN113797979B (en) * | 2021-09-15 | 2022-12-20 | 中国科学院长春应用化学研究所 | Modified nano particle, preparation method and application thereof |
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| Publication number | Publication date |
|---|---|
| CN105237764B (en) | 2017-07-28 |
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