WO2016052981A1 - Procede de fabrication de capsules creuses de carbone - Google Patents

Procede de fabrication de capsules creuses de carbone Download PDF

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Publication number
WO2016052981A1
WO2016052981A1 PCT/KR2015/010295 KR2015010295W WO2016052981A1 WO 2016052981 A1 WO2016052981 A1 WO 2016052981A1 KR 2015010295 W KR2015010295 W KR 2015010295W WO 2016052981 A1 WO2016052981 A1 WO 2016052981A1
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WIPO (PCT)
Prior art keywords
carbon
acid
polymer particles
particles
hollow carbon
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PCT/KR2015/010295
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English (en)
Korean (ko)
Inventor
김인영
이진영
손권남
황의용
권원종
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주식회사 엘지화학
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Priority claimed from KR1020150137058A external-priority patent/KR101783446B1/ko
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to JP2017508968A priority Critical patent/JP6524215B2/ja
Priority to CN201580051800.9A priority patent/CN106794990B/zh
Priority to US15/512,694 priority patent/US10821687B2/en
Publication of WO2016052981A1 publication Critical patent/WO2016052981A1/fr

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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
    • B01J13/02—Making microcapsules or microballoons
    • B01J13/04—Making microcapsules or microballoons by physical processes, e.g. drying, spraying
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B32/00—Carbon; Compounds thereof
    • C01B32/05—Preparation or purification of carbon not covered by groups C01B32/15, C01B32/20, C01B32/25, C01B32/30

Definitions

  • the present invention relates to a production method capable of mass production of hollow carbon capsules.
  • Hoi low carbon capsule refers to particles in which the shell having a pore inside and forming a p 0re is made of carbon. Due to the internal pore of the hollow carbon capsule, the surface area is wide, and the pore can serve as a storage space.
  • the hollow carbon capsulum has various uses such as adsorbents, hydrogen storage materials, additives, catalyst supports, and lubricants.
  • the manufacturing principle of the hollow carbon capsule is to form the structure of the template core and the carbon precursor shell, and then remove the template. At this time, it is divided into a method of using a hard template and a method of using a sof t template according to the type of template used.
  • the method of using a hard template is a method of using an inorganic material of silica or metal oxide film as a template.
  • Hard template is easy to maintain the pore structure because there is almost no change in shape during carbonization, there is an advantage that the shape of the pore can be easily adjusted by adjusting the shape of the hard template.
  • the carbonization process requires the formation of a carbon shell and then the removal of the hard template. The shell formation and the pore formation are divided into two stages. In general, the removal of the hard template with toxic acidic or basic materials causes environmental problems. have.
  • the method of using a soft template is a method of using an organic material capable of thermal decomposition such as a polymer as a template.
  • the polymer used as a template is thermally decomposed and removed, and at the same time, carbonization of the carbon precursor proceeds at the same time, so the process is simple and no toxic substance is used.
  • the pyrolysis and carbonization of the polymer proceed simultaneously and the form of the formed pore is likely to collapse, care must be taken in selecting the material compared to the method using a hard template.
  • the method of using a soft template has two main considerations, one is to prepare particles of the core part of the soft template and the shell part of the carbon precursor before the carbonization process, and the other is the material of the soft template and the carbon precursor.
  • thermal properties of the two materials are similar, an additional process is required because the shape of the formed pore is likely to collapse.
  • a method of carbon-coating the surface of polystyrene particles with glucose having similar thermal properties to form a core (polystyrene) / shell (carbon) structure and heat-treating the same has been reported (Robin J). White et al., J. Am. Chem. Soc., 2010, 132: 17360-17363).
  • this method requires about 24 hours of glucose pretreatment in the autoclave to form carbon shells, which is not suitable for mass production because of the long process time. not. Therefore, the thermal properties of the soft template and the carbon precursor must be distinguished.
  • the carbon precursor forms the carbon shell
  • a material that can maintain the structure of the carbon shell to be formed must be selected. Therefore, there is a need for a method for producing hollow carbon capsules that are suitable for mass production while using soft templates and that can maintain the shape of pore well. Therefore, the inventors of the present invention while studying a method for mass production of hollow carbon capsules, using the polymer particles as a soft template, spray and drying (spray-drying) method, using a simple and effective production of hollow carbon capsules It was confirmed that the present invention was completed.
  • the present invention is to provide a manufacturing method capable of producing a hollow carbon capsule simply and effectively.
  • the present invention is to provide a vacuum-type carbon capsule produced by the above production method.
  • the present invention provides a method of manufacturing a hollow carbon capsule comprising the following steps:
  • Step 1 Preparing a spray solution comprising a carbon precursor, polymer particles, and a solvent (step 1);
  • the term "hol low carbon capsule” refers to a particle having a core / shell structure in which the core portion is a pore and the shell portion is made of carbon.
  • the hollow carbon capsule prepared in the present invention may be prepared in a form in which they are aggregated together. When manufactured in a clustered form, each shell has a structure that connects to another shell. An example of a hollow carbon capsule according to the present invention is shown in FIG. 6.
  • the pore can be used as an adsorbent, a hydrogen storage material, an additive, a catalyst support, a lubricant, and the like.
  • the principle of producing hollow carbon capsules according to the invention is to produce particles of the core / shell structure and then to remove the material of the core while maintaining the structure of the shell. In other words, removal of the core material and formation of the carbon shell must occur simultaneously through the heat treatment.
  • step 1 is a step of preparing a spray solution for spraying and drying, the step of preparing a spray solution containing a carbon precursor, polymer particles and a solvent.
  • the polymer of the polymer particles may be used one or more, and may be polystyrene, poly (methyl methacrylate), polypropylene, polyethylene, polyurethane, polyvinyl alcohol, polyvinylacetate or ethylene-vinyl acetate.
  • the polymer of the polymer particles is polystyrene.
  • the polymer particles can be easily purchased commercially, in the case of polystyrene particles can be easily prepared by the emulsion polymerization method.
  • the emulsion polymerization process comprises the steps of adding to a polystyrene monomer and an emulsifier * solvent; And it can be prepared by the step of polymerization by adding an initiator. Water may be used as the solvent, and SDS (sodium dodecyl sul fate) may be used as the emulsifier.
  • the emulsion polymerization method has the advantage of controlling the size of the polystyrene particles by controlling the content of the emulsifier and monomer.
  • the carbon precursor is characterized in that it crosslinks at a temperature lower than the thermal decomposition temperature of the polymer particles. That is, the carbon precursor and the polymer particles have different thermal behavior depending on temperature.
  • FIG. 2 Experimental Example 1
  • polystyrene particles are pyrolyzed at 400-450 ° C.
  • lignosulfonate an example of a carbon precursor that can be used in the present invention
  • the carbon precursor is crosslinked in the vicinity of 200 ° C.
  • the core portion may be thermally decomposed to form empty spaces occupying the space, and carbon precursors in the shell portion may be carbonized to form carbon shells.
  • the carbon precursor may be used one or more, preferably a substance having aromaticity and soluble in water. Examples of carbon precursors having the above characteristics include lignosulfonate, tannic acid, gallic acid, vanillic acid, dopamine, folic acid, and caffe.
  • Acids (caffeic acid, rosmarinic acid, chlorogenic acid, ferulic acid, sinapinic acid, ellagic acid and ellagitannins).
  • the ellagitannin-based compounds include castalazine, castal in, casuarictin, grandinin, punicalagin and punicalin, Roburin A, telimagrandin, and terflavin B.
  • lignosulfonate may be used as the carbon precursor.
  • the diameter of the polymer particles corresponds to the pore diameter of the hollow carbon capsule to be finally produced, and may be appropriately selected depending on the intended use.
  • polymer particles having a diameter of 10 nm to 20,000 nm may be used.
  • the weight ratio of the carbon precursor and the polymer particles in the spray solution is preferably 0.07: 3 to 70: 3.
  • the thickness of the carbon shell can be controlled by adjusting the content of the carbon precursor, and the higher the content of the carbon precursor, the thicker the carbon shell.
  • the spray solution may further include carbon nanotubes. When the carbon nanotubes are used together, the carbon nanotubes remain during the heat treatment to be described later, so that the structure of the carbon shell can be stably maintained, and the electrical conductivity and the mechanical properties can be improved by the inherent characteristics of the carbon nanotubes.
  • the carbon nanotubes may be single-walled carbon nanotubes, double-walled carbon nanotubes and multi-walled carbon nanotubes.
  • the length of the carbon nanotubes is preferably 0.5 ⁇ ⁇ to 50 ⁇ ⁇ . It is preferable to sonicate the spray solution containing the carbon nanotubes so that the carbon nanotubes may be well dispersed in the spray solution.
  • the weight ratio of the carbon nanotubes and the carbon precursor in the spray solution is preferably 1.5: 1 to 10: 1.
  • Step 2 is a step of preparing particles of the core / shell structure, the step of preparing the particles by spraying and drying the spray solution prepared in step 1.
  • the spray-drying method is a method widely used in the manufacture of foods, medicines, ceramics, and the like.
  • Step 3 is a step of finally manufacturing the hollow carbon capsule, and heat treating the particles prepared in step 2 to carbonize the carbon precursor and remove the polymer particles.
  • the polymer particles are thermally removed through the heat treatment to form pores, and the carbon precursors are carbonized to form carbon shells.
  • the heat treatment temperature is controlled to a temperature that pyrolyzes the polymer particles and carbonizes the carbon precursor, preferably 200-35 (first treatment at C and second treatment at 400-60CTC. thermal polymer i zat ion,
  • the shell-shaped solid carbon through a primary treatment, it is possible to generate.
  • the secondary treatment temperature is a temperature at which the polymer particles are pyrolyzed, and the polymer particles may be removed through the secondary treatment to form pores.
  • the primary silver and the secondary temperature may be applied respectively, or a method of gradually increasing the temperature in a range including both the primary temperature and the secondary temperature may be applied.
  • the temperature was raised from room temperature (25 ° C) to 400 ⁇ 600 ° C, it is preferred to heat treatment for 2 hours at 400 ⁇ 600 ° C.
  • the temperature is preferably raised to 10 ° C / min.
  • the carbon nanotubes are additionally used in the step 1, since the carbon nanotubes are maintained as they are, the structure of the intertwined carbon nanotubes is maintained, and the polymer particles are removed by pyrolysis. It is possible to maintain the formed empty space (pore) stably.
  • the carbon nanotubes can impart electrical conductivity and mechanical strength to the hollow carbon capsule, and thus, the shape can be stably maintained even when the hollow carbon capsule is used under severe conditions.
  • the method for producing the hollow carbon capsule according to the present invention has the advantage of using a spraying and drying method to form a core / shell structure, using no toxic substances, reducing environmental problems, and being suitable for mass production.
  • the spray solution is an aqueous solution
  • a material that is well dispersed in water may be applied to change the properties of the hollow carbon capsule to be manufactured.
  • polymer particles which are soft templates by using polymer particles which are soft templates, pore formation and carbon shell formation are possible at the same time, and there is an advantage that the process is simple.
  • a carbon precursor a material that is inexpensive and easy to handle may be used, and thus, the process may be easy and manufacturing cost may be reduced.
  • the present invention provides a hollow carbon capsule prepared by the above production method. An example of a hollow carbon capsule made in accordance with the present invention is shown in FIG. 6. In the hollow carbon capsul, the diameter of the inner pore is 10 nm to 20, 000 mm 3.
  • the carbon shell has a thickness of 1 nm to 1,000 nm.
  • the diameter of the entire hollow carbon capsule is 12 nm to 22,000 nm.
  • Hollow carbon capsules produced according to the present invention is characterized in that the pore is uniformly formed as a rigid shell, and the shape of the shell is well maintained without being broken. Accordingly, the hollow carbon capsule manufactured according to the present invention can be used as an adsorbent, a hydrogen storage material, an additive, a catalyst support, a lubricant, and the like by utilizing a large surface area and an inner space.
  • the hollow carbon capsule can be produced simply and effectively by using the polymer particles as a soft template and by using a spray-drying method.
  • FIG. 1 schematically shows a method of manufacturing the hollow carbon capsule of the present invention.
  • FIG. 2 graphically shows the TGA results of polystyrene (PS) and lignosulfonate (LS). '
  • Figure 3 is a graph showing the TGA results with the increased carbon capsule according to an embodiment of the present invention.
  • FIG. 4 is a graph showing the BET surface area and the pore distribution (FIG. 4A) and the Isotherm dot result (FIG. 4B) of the hollow carbon capsule according to the embodiment of the present invention.
  • FIG. 5A shows polystyrene particles
  • FIG. 5B shows particles of PS core / LS shell before heat treatment
  • FIG. 5C shows particles of PS core / LS shell after heat treatment.
  • Figure 6 shows the pore and carbon shell of the hollow carbon capsule according to an embodiment of the present invention.
  • Figure 7 shows an SEM image of a hollow carbon capsule according to an embodiment of the present invention.
  • Figure 8 shows a TEM image of a hollow carbon capsule according to an embodiment of the present invention.
  • FIG. 9 is a graph showing the BET surface area (FIG. 9A) and the pore distribution (FIG. 9B) of the vaporized carbon capsule according to the embodiment of the present invention.
  • Figure 10 shows the powder resistance measurement results of the hollow carbon capsule according to an embodiment of the present invention.
  • polystyrene particles used as soft templates were prepared. Specifically, 0.1 g of sodium dodecyl sulfate (SDS) was added to 90 mL of distilled water, followed by stirring (300 rpm) while raising the temperature to 80 ° C. to dissolve SDS. 10 g of styrene was added to the solution and mixed for 10 minutes. 0.1 g of the initiator KPSCpotassium persulfate) was completely dissolved in 10 mL of distilled water, which was then added to the styrene-dissolved solution and polymerized for 6 hours to prepare the polystyrene particles in a sol state (10 wt% PS sol.) . The prepared polystyrene particles are shown in Figure 5 (a), the diameter of the particles was about 200 nm.
  • SDS sodium dodecyl sulfate
  • the manufacturing method of the hollow carbon capsule according to the present invention is schematically illustrated in FIG. 1. Specifically, 1 g of lignosulfonate was added to 200 mL of distilled water, and completely dissolved using bath sonication. 10 wt PS sol prepared in Preparation Example in the solution. 30 mL was added and mixed with a homogenizer to prepare a spray solution. Spray and dry the spray solution with a Spray-dryer (Outlet temp .: 180 ° C, aspirator: 95%, feeding rate: 15%), and heat the temperature up to 600 ° C at a rate of 10 ° C / min in a tube furnace. After raising for 2 hours at 600 ° C. (Ar condition), a hollow carbon capsule was prepared.
  • Thermogravimetric analysis was performed to confirm the temperature-dependent behavior of lignosulfonate and polystyrene in the heat treatment process. Specifically, the weight according to temperature was measured for each of the used lignosulfonate (LS) and the polystyrene particles, and the results are shown in FIG. 2. As shown in FIG. 2, the lignosulfonate (LS) exhibited a constant mass loss with increasing temperature, and thermal polymerization occurred at about 200-35 CTC, indicating that about 45 wt% of carbon remained after the entire process.
  • the lignosulfonate can be assumed to have about 45% by weight of carbon remaining. Therefore, the content of lignosulfonate in the final hollow carbon capsule is theoretically about 11% by weight (0.25 X 0.45), which is consistent with the result of FIG.
  • the specific surface area and pore volume of the prepared hollow carbon capsule were measured as shown in FIG. 4. As a result, the BET surface area was measured to be 126.9483 m 2 / g and the pore volume was 0.328744 cmVg. 5) Observation of hollow carbon capsule
  • the prepared hollow carbon capsule was observed in a microscope as shown in FIG. 5, and polystyrene particles and core / shell particles before the heat treatment process were also observed for comparison.
  • Fig. 5 (a) shows the polystyrene particles before spraying, which are spherical particles having a diameter of about 200 nm.
  • Figure 5 (b) shows the core / shell particles before the heat treatment process, the total diameter is about 1000-3000 nm and polystyrene particles were observed inside.
  • 5 (c) shows the hollow carbon capsule after the heat treatment process, where pore was observed in the place where the polystyrene was removed, and it was observed that the carbon shell did not collapse and maintained its shape well. 6, the hollow carbon capsule was observed in more detail with a microscope.
  • the spray solution Spray-dryer (Out 1 et temp .: 180 ° C, aspirator ⁇ '95%, feeding rate: 15%) by spraying and drying, in a tube furnace at a rate of TC / min to a temperature 600 ° C After raising and calcining at 600 ° C. for 2 hours (Ar conditions), hollow carbon capsules were prepared. 2) Observation of the hollow carbon cap
  • the hollow carbon capsule prepared in Example was observed under a microscope.
  • FIG. 7 SEM images are shown in FIG. 7 and TEM images are shown in FIG. 8.
  • FIG. 7 it was confirmed that the form of pore was well maintained after carbonization, and the pore diameter was about 20C 220 nm, which was almost the same as the diameter of the polystyrene particles prepared in Preparation Example. From this, it was confirmed that the space in which the polystyrene particles were removed was well maintained as a pore.
  • FIG. 8 it was confirmed that the carbon nanotubes in the form of entangled in the hollow carbon capsule maintains the pore structure.
  • the BET surface area was 133.5264 m 2 / g
  • the pore volume was 0.309500 cm 3 / g.
  • the powder resistance of the hollow carbon capsule prepared in the above example was measured.
  • the powder resistance of the hollow carbon capsule prepared in Example 1 was also measured for comparison. Specifically, 1 g of each hollow carbon capsule was placed in a powder holder, and a bar was added. This was mounted on a powder resistance measuring device (HPRM-1000, Hantech Co., Ltd.), and then the sheet resistance, electrical conductivity, and packing density were measured while pressing the cylindrical bar at a constant pressure. The results are shown in FIG. 10 and Table 1 below.
  • the hollow carbon kaepseul of Example 2 containing the carbon nanotubes showing a high electric conductivity of approximately 10 5 times greater than that in Example 1.
  • the hollow carbon capsule according to the present invention can be confirmed that the conductive pathways are formed internally and externally due to the carbon nanotubes, thereby significantly improving the electrical conductivity.
  • the conductivity increased as the measured pressure increased.

Abstract

La présente invention concerne un procédé de fabrication de capsules creuses de carbone au moyen de particules de polymère sous la forme d'un modèle souple et utilisant un procédé de séchage par pulvérisation, permettant ainsi la fabrication simple et efficace des capsules creuses de carbone.
PCT/KR2015/010295 2014-09-30 2015-09-30 Procede de fabrication de capsules creuses de carbone WO2016052981A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
JP2017508968A JP6524215B2 (ja) 2014-09-30 2015-09-30 中空型炭素カプセルの製造方法
CN201580051800.9A CN106794990B (zh) 2014-09-30 2015-09-30 中空碳胶囊的制备方法
US15/512,694 US10821687B2 (en) 2014-09-30 2015-09-30 Method for producing hollow carbon capsules

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
KR10-2014-0131859 2014-09-30
KR20140131859 2014-09-30
KR20140131860 2014-09-30
KR10-2014-0131860 2014-09-30
KR1020150137058A KR101783446B1 (ko) 2014-09-30 2015-09-25 중공형 탄소 캡슐의 제조 방법
KR10-2015-0137058 2015-09-25

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018186003A1 (fr) * 2017-04-07 2018-10-11 株式会社神戸製鋼所 Procédé de production de particules de carbone poreux et particules de carbone poreux

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018186003A1 (fr) * 2017-04-07 2018-10-11 株式会社神戸製鋼所 Procédé de production de particules de carbone poreux et particules de carbone poreux

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