US20040024074A1 - Porous carbons - Google Patents
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- US20040024074A1 US20040024074A1 US10/344,248 US34424803A US2004024074A1 US 20040024074 A1 US20040024074 A1 US 20040024074A1 US 34424803 A US34424803 A US 34424803A US 2004024074 A1 US2004024074 A1 US 2004024074A1
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- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B35/00—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
- C04B35/515—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products based on non-oxide ceramics
- C04B35/52—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products based on non-oxide ceramics based on carbon, e.g. graphite
- C04B35/524—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products based on non-oxide ceramics based on carbon, e.g. graphite obtained from polymer precursors, e.g. glass-like carbon material
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- 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
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- 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
- C01B32/30—Active carbon
- C01B32/312—Preparation
- C01B32/318—Preparation characterised by the starting materials
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- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B38/00—Porous mortars, concrete, artificial stone or ceramic ware; Preparation thereof
- C04B38/0051—Porous mortars, concrete, artificial stone or ceramic ware; Preparation thereof characterised by the pore size, pore shape or kind of porosity
- C04B38/0064—Multimodal pore size distribution
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- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B38/00—Porous mortars, concrete, artificial stone or ceramic ware; Preparation thereof
- C04B38/009—Porous or hollow ceramic granular materials, e.g. microballoons
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- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B2235/00—Aspects relating to ceramic starting mixtures or sintered ceramic products
- C04B2235/70—Aspects relating to sintered or melt-casted ceramic products
- C04B2235/74—Physical characteristics
- C04B2235/77—Density
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/24—Structurally defined web or sheet [e.g., overall dimension, etc.]
- Y10T428/24273—Structurally defined web or sheet [e.g., overall dimension, etc.] including aperture
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
Definitions
- the present invention relates to improved phenolic resin structures which can be used as ion exchange resins and can be used to prepare porous carbon materials and to a methods for making these.
- the ion exchange powders can be produced by either bulk curing of the resin followed by milling (e.g. WO91/09891) to produce a low porosity powder or by reversed phase condensation (TJnitaka Ltd U.S. Pat. No. 4,576,969 1986).
- milling e.g. WO91/09891
- reversed phase condensation TJnitaka Ltd U.S. Pat. No. 4,576,969 1986.
- One of the limitations of these materials was limited intenal porosity and they were rapidly replaced by the highly porous sulphonated styrene divinyl benzene copolymer based ion exchange resins when these became available.
- phenolic based resins have largely disappeared, specific applications do still exist in food related industries based on their underlying performance characteristics.
- the phenolic resins can be carbonised to form mesoporous carbons.
- Mesoporous carbons are used as adsorbents or catalysts supports and can be used in spherical, granular of thin film form.
- Existing production methods use gas phase and chemical activation routes to produce mesoporous carbons but, activated carbon, as conventionally produced, is normally microporous ( ⁇ 2 nm pore diameter—IUPAC definition) with little or no pore volume in the mesopore (2-50 nm) and macropore (>50 nm) range.
- IUPAC definition microporous
- evaporative emission control when used as a catalyst support, particularly in liquid phase applications, this is a major drawback.
- Chemical activation can also be used to directly produce mesoporous carbons by pelleting or extruding a plasticised acidic lignin base char and then directly carbonising and activating the mixture as disclosed in U.S. Pat. No. 5,324,703.
- the production route also leads to a low macroporosity, which can have disadvantages in catalytic and liquid phase processes.
- the route also has the disadvantage of requiring compounds such as phosphoric acid and zinc chloride as the activating agents, which can cause severe environmental problems and have a major impact on the materials of construction of the process plant.
- a method for forming a porous resin structure which method comprises the condensation of a nucleophilic component with an electrophilic cross-linking agents in solution in the presence of a pore former.
- the condensation can be catalysed or non catalysed.
- the invention also provides a method for forming a porous carbon structure in which the porous resin is carbonised to form the porous carbon structure.
- the nucleophilic component can be for example phenol, a phenolformaldehyde pre-polymer—a Novolac optionally together with a modifying agent.
- the electrophilic component can be for example formaldehyde, hexamine, furfural.
- the pore former acts as the solvent.
- Methods for preparation of the porous polycondensation resins generally comprise dissolving nucleophilic components (e.g. phenol, Novolac, modifying reagents) and electrophilic cross-linking components (e.g. formaldehyde, hexamine, furfural) in the pore former with or without catalysts (acidic or basic) and thermosetting the solution obtained to produce cured, solid, insoluble and infusible resins with the pore former evenly distributed within the resin matrix creating pores of controlled size.
- nucleophilic components e.g. phenol, Novolac, modifying reagents
- electrophilic cross-linking components e.g. formaldehyde, hexamine, furfural
- the invention is particularly useful for producing porous carbons which can be carbonised to mesoporous/macroporous carbons.
- mesoporous carbon we mean here a carbon possessing alongside micropores, pores with diameter from ca.2 nm to ca. 50 nm and by macroporous a carbon possessing alongside micropores pores with diameters larger than 50 nm , as measured by nitrogen adsorption and mercury porosimetry methods and as defined by IUPAC.
- the phenolformaldehyde condensation pre-polymer can be a Novolac resin.
- Novolac resins are typically produced by the acid catalysed condensation of phenol and formaldehyde in approximately equimolar amounts.
- Novolacs are usually thermoplastic solid polymers that melt at or above 100° C. depending on the average molecular weight. They are essentially linear chains with molecular weights of from 500 to 2000 D, where phenolic moieties are linked with methylene (predomitly) and methylene ether bridges and possess one nucleophilic active site, predominantly in the unsubstiteted ortho-position to hydroxyl group. There can be also varying degrees of chain branching depending upon the production conditions.
- Nitrogen containing compounds that are active in polycondensation reactions such as urea, aromatic (aniline) and heteroaromatic (melamine) ammes. These allow the introduction of specific types of nitrogen functionality into the initial polymer (and final carbon) and influence the development of the mesoporous structure of both the resins and the final carbons.
- nucleophilic modifying reagents which can be used in the present invention possess two and more active sites and are more reactive in condensation reactions than phenol or Novolacs. It means that they are first to react with primary cross-linking agents forming secondary cross-linking agents in situ In the case of melamine it is preferable to prepare the secondary cross-linkidg agent—hydroxymethylated melamine—in advance.
- Novolacs are thermally stable in that they can be heated and cooled repeatedly without structural change. They are cured on addition of cross-linking agents and heating.
- the process of the invention is carried out in solution and the pore former can also be the solvent
- the pore former can also be the solvent
- a solution obtained from commercial Novolac pre-polymers together with modifying reagents (if required), cross-liking agents and catalysts (if required) and an appropriate amount of the pore former as a solvent, is heated to bring about the cross-linking reaction, resulting in a solid resin.
- the solid porous polycondensation resins which can be used in the invention can be produced directly from phenol (and optionally modifying agents) and formaldehyde (or other cross-linking agents) on heating their solution in the pore former with the catalyst (acidic or basic).
- reaction solution will set during the cross-linking reaction if the correct composition is used “locking” the pore former into the resin structure and creating a mesoporous resin.
- the porous resin precursor can be cast into a block and comminuted to give a powder of particle size in the range of 1 to 1000 microns.
- This resin powder can then be carbonised to give a porous carbon with a pore size which can be controlled e.g. to give a mean pore size of between 2 and 50 nm (mesopores) or greater than 50 nm (macropores) and also with micropores with a mean pore size between 0.6 and 2 nm.
- the viscous solution of the partially cross-linked pre-polymer is poured into a hot liquid such as mineral oil containing a dispersing agent and the mixture stirred, the pre-polymer solution will form into beads. These are initially liquid and then, as curing proceeds, they become solid.
- the average bead particle size is controlled by several process parameters including the sirer type and speed, the oil temperature and viscosity, the pre-polymer solution viscosity and volume ratio of the solution to the oil and can be adjusted between 5 and 2000 microns. These beads can then be filtered off from the oil and, after pore former removal, pyrOlysed to give meso- or macroporous carbon beads.
- solvents that can be employed as the pore formers.
- the key requirements for these solvents are: high solubility/compatibility of the reaction components in the solvent; useable viscosity of the pre-polymer/cross-linking agent/solvent solution (this for instance essentially rules out glycerol which gives an unacceptably high viscosity); reasonably high boiling temperature to perform the polycondensation reaction at a reasonable rate without significant solvent evaporation.
- Pore formers which can be used include but are not limited to: ethylene glycol, 1,4-butylene glycol (diols); diethylene glycol, triethylene glycol (diols-ethers); gamma-butyrolactone, propylene carbonate (cyclic esters); dimethylformamide, N-methyl-2-pyrrolidinone (substituted amides, cyclic and linear); monoethanolamine (aminoalcohol).
- the pore former In the presence of a low level of pore former the pore former is compatible with, and remains within, the cross-linked resin domains, (e.g., ⁇ 120 parts/100 parts Novolac for the Novolac-Hexamine-Ethylene Glycol reaction system), whilst the remainder forms a solution with the partially cross-linked polymer between the domains.
- the pore former adds to the light polymer fraction increasing the volume of material in the voids between the domains that gives rise to the mesoporosity.
- the higher the pore former content the wider micropores and the higher the pore volume.
- This phase separation mechanism then provides a variety of ways of controlling the pore development in the cross-linked resin structures. These are: chemical composition and concentration of the pore former; chemical composition and quantity of the cross-linking electrophilic agents, presence, chemical nature and concentration of modifying nucleophilic agents, chemical composition of phenolic nucleophilic components (phenol, Novolac), presence, chemical nature (acidic, basic) and concentration of the catalyst.
- the solvent should also be incompatible with the oil and compatible with water in order to secure the formation of a “water in oil” type emulsion with the beads of the resin solution dispersed in the bulk of the oil, minimise the solvent extraction into the oil and problems with its recovery and enhance simple recovery of the solvent from the solid resin beads by washing with water.
- Some pore formers under special conditions, are also able to contribute to the cross-linking process.
- active carbocations can be formed from ethylene glycol in strong acidic media or the methylol derivatives of monoethanolamine and formamide with formaldehyde, which will react as secondary cross-linking agents.
- the primary cross-linking agents used in the invention are formaldehyde, furfural and hexamethylenetetramine (hexamine).
- Formaldehyde is introduced either in solution in the pore former or as solid paraformaldehyde, (CH 2 O) x .
- Formaldehyde cross-links phenolic moieties forming —CH 2 — and —CH 2 —O—CH 2 —bridges at ratios depending on the pH of the reaction mixture.
- Methylene bridges are the only ones formed in strong acidic and strong alkali media, whereas at pH's close to neutral either type of bridges appear. Water is formed as the stoichiometric secondary condensation product at a level depending on the type of bridge formed.
- the “condensation” water may then influence the phase separation and mesopore formation process by reducing the compatibility of the water containing pore former with the resin domain depending on the pore forming solvent being used.
- Furfural differs from formaldehyde in that the electrophilic reactivity of its carbonyl group is supplemented by the high nucleophilic activity of the heterocycle. Moreover, ring scission and consecutive reactions can give a wide range of products, which can provide additional cross-linking paths, possibly involving phenolic hydroxyls. These are typical for furan resin derivatives, especially in acidic media and, in combination with other cross linking agents, provide an additional route to modify both the chemical structure and porosity of the resins.
- Hexamine can be introduced as a powder directly into the reaction solution. On heating ring cleavage occurs, catalysed by traces of water and, possibly, protonic solvents, resulting in the formation of the active species—aminocarbinols. On cross-linking these form different bridges, including simple methylene and more complex—nitrogen-containing groupings like bis-methylene amine, tris-methylene amine and 1,3-oxazine.
- the low molecular weight condensation by-products are water, that then cleaves the next portion of hexamine, and ammonia Ammonia, though highly volatile at the reaction conditions, increases the pH of the reaction solution when no acidic or basic catalysts are present, which may also affect the phase separation and mesopore formation process.
- hexamine is preferably used for cross-linking Novolac resin at a concentration of 9 weight parts hexamine per 100 weight parts of Novolac. This ensures the formation of the solid resin with maximal cross-linking degree. This is in contrast to previously disclosed sintered resin structures where typicaly up to 3 parts of hexamine per 100 parts of Novolac were used (EP 0245551).
- hexamine is used in the ethylene glycol solution at a level of 3 weight parts per 100 weight parts of Novolac only non-porous semi-solid rubbery material is obtained, whereas at 9 weight parts level a highly mesoporous and solid resin is produced. It is thought that ethylene glycol might act as an internal plasicizer when the cross-linking degree is not adequate.
- Novolac primary cross-linking agent—modifying agent reaction system.
- the modifying agent reacts rapidly with the primary cross-linking agent forming a secondary cross-linking agent that then binds the Novolac chains together.
- the resin consists of homocondensed phenolformaldehyde chains bridged with nitrogen-containing groupings (or resorcinol or hydroquinone derived moieties).
- Phenol cross-linking agent—modifying agent—strong acidic or strong basic catalyst. Separate homocondensation processes occur for the two different nucleophilic reagents (phenol and modifying agent). This then results in the formation of a binary resin matrixes where the two resin components behave in a different way on thermal treatment.
- Phenol cross-linking agent—modifying agent—weak acidic or weak basic catalysts, or no catalyst at all. This leads to a co-condensation process with formation of structurally homogeneous material with modifying moieties evenly distributed within phenolic resin.
- the development of mesoporosity within a resin of constant composition is also dependent upon the rate of the cross-linking reaction.
- the condensation reaction rate can be controlled by the reaction temperature and also via heat transfer phenomena which are controlled by the physical form of the resin (block, beads, etc). This is found in the preparation of the spherical resin, where heat transfer phenomena can be ignored because the process is carried out in hot oil with small resin droplets. If the solid cured spherical resin is prepared from a solution of Novolac and hexamine in ethylene glycol by smoothly increasing the temperature to 100-105° C. (solution quite close to gel state), dispersing the solution into the oil at about the same temperature, and then gradually raising the temperature to 150-160° C.
- a highly mesoporous resin is formed.
- the mesoporosity of the resulting cured resin will be dramatically decreased.
- the first resin produces highly mesoporous carbon with moderate to low microporosity.
- the second resin produces carbon with relatively high microporosity, but low mesoporosity.
- the way in which the pore former is removed from the cured resin can be important to the generation of the porosity in corresponding carbon. If the pore former (e.g., ethylene glycol) is removed simply on pyrolysis during the carbon production, the mesoporosity may be lost It has been found that it is preferable to remove the pore former at a low temperature, e.g., below 100° C., via washing the resin with water or vacuum distillation, with subsequent recycling of the pore former. The washing (sometimes—after neutralisation) becomes absolutely necessary, when alkalis or sulphuric acid are used as catalysts. This is because alkalis will affect the carbonisation process, sometimes in very undesirable way, whereas sulphuric acid will contaminate the carbon with sulphur, reducing its value as a catalysts supports.
- a low temperature e.g., below 100° C.
- hetero atoms can be incorporated in the resin structure.
- Metals such as copper, nickel, chromium etc, can be incorporated in the porous resin structure by incorporating the metal as a solution of a salt in the pore forming solvent prior to cross linking the resin and non metals and metalloids can be incorporated directly into the mesoporous resin and thence into the mesoporous carbons.
- an inorganic compound is soluble in the pore former it can be added directly to the initial reaction solution
- the preparation procedure is then carried out in the usual way.
- the metal species are then evenly distributed within the resin matrix.
- the hydroxy- or aminogroups of phenolic resin enhances the initial distribution to the atomic level. Incorporation of the highly dispersed element within the resin then leads to a high dispersion of the element in the carbon formed during pyrolysis.
- the transformation of the porous resins in any physical form and shape into the porous carbons of the invention is performed by carbonisation, i.e. high temperature treatment in an inert atmosphere and at temperatures from ⁇ 600° C. upwards.
- the pyrolysis process commences at about 400° C. and is largely complete by around 700° C. although further small weight losses continue up to around 1400° C.
- surface area development is only significant above around 600° C. at which point the material is not strictly carbon
- the development of a significant electrical conductivity is only observed at above 700° C.
- the inert atmosphere for the pyrolysis can be secured by the appropriate gas flow.
- Nitrogen and argon can be used as inert purge gases at any temperature whilst carbon dioxide is effectively inert up to around 800° C. in the absence of catalytic metals. Vacuum may also be used although this can lead to the development of molecular sieving behaviour. Due to the presence of mesopores in these materials, which provide efficient escape routes for the volatile products, the heating rates employed can be very high—up to 10° C. per minute.
- the porosity of the carbons can be further enhanced by conventional activation methods, e.g. by activation in steam above 750° C. or carbon dioxide above 800° C., which can give surface areas as measured by BET 5 point method of up to 2000 m 2 /g.
- the size distribution of the spheres can be controlled to give a dispersion of D90AD10 of better than 10 (preferably better than 5) and the larger pores can be controlled from a mean diameter of 2 nm up to 50 nm (mesopores) or greater than 50 nm (macropores) and where the mean micropore diameter can be controlled to between 0.6 and 2 nm to give
- the materials of the present invention can be advantageously used in a wide variety of demanding applications where the high physical strength and high attrition resistance offer special benefits. These include, but are not limited to, liquid phase catalyst supports, blood filtration and any application where the carbon is used in a fluid bed or moving bed environment.
- the large mesopores can also be advantageously utilised in system where larger molecules are either adsorbed or grafted within the pores. These can include drug release systems, chiral supports etc.
- the invention is illustrated in the following examples.
- SA weight Condensation Residence # EG, weight parts parts temperature, ° C. time, minutes 1 259 35.4 72 ⁇ 1 80 2 370 45 77 ⁇ 1 120 3 259 17.0 72 ⁇ 1 300
- the resulting viscous solution was poured as a stream into 2-4 volumes of stirred preheated (110-115° C.) mineral oil containing 0.5% of a drying oil, acting as a dispersing agent.
- the temperature of the resulting mixture dropped to 100-102° C., and cross-linking occurred normally within 1-2 minutes.
- the resulting slurry was gradually heated up to 115-120° within 30-60 minutes to complete the curing and cooled down. Resin in bead form was filtered off from the oil, washed several times with hot water to remove both pore former and catalyst.
- the resulting porous spherical resin containing water, residual oil, traces of pore former and catalyst can then be directly carbonised to produce spherical porous carbon
- organic solvent preferably with ethanol-ether 1:1 v/v solution
- a reaction mixture containing 94 weight parts of phenol, specified amounts of aniline (A), ethylene glycol pore former, paraformaldehyde and concentrated sulphuric acid was heated with stirring up to specified condensation temperature (complete paraformaldehyde dissolution occurs around 60° C.) and maintained at this temperature for specified residence time (see Table 2-1).
- TABLE 2-1 EG, PF, A, SA, weight weight weight weight Condensation Residence # parts parts parts parts temp. ° C. time, min. 1 272 56.7 4.7 37.2 73 ⁇ 1 105 2 284 59 9.3 39 73 ⁇ 1 115 3 310.5 64.8 18.6 42.4 73 ⁇ 1 140 4 336.2 70.2 27.9 45.9 73 ⁇ 1 180
- the resulting porous spherical resin containing water, residual oil, traces of pore former and low molecular weight fraction was carbonised by heating at 800° C. in flowing carbon dioxide to produce the spherical porous carbon. If the resin beads are carbonised directly after separation from the oil, without washing, the porosity of resulting carbons decreases.
- the sample of resin should be washed repeatedly with organic solvent, preferably with ethanol-ether 1:1 v/v solution, and dried in vacuo until constant weight
- the pore size distribution graphs and some structural parameters of both resins and carbonised materials are presented on FIGS. 3 a and 3 b and Tables 3-2 and 3-3, respectively.
- FIG. 3 b shows the effect of the pore former in resin composition on the porosity of corresponding carbonised materials.
- TABLE 3-3 BET area, m 2 /g Pore Volume (P/P 0 0.98), cm 3 /g Carbon 3.1 473.2 0.26 Carbon 3.2 468.3 0.30 Carbon 3.3 592.2 0.48 Carbon 3.4 567.3 0.54 Carbon 3.5 579.6 0.88 Carbon 3.6 525.1 1.02 Carbon 3.7 469.3 1.13 Carbon 3.8 482.0 0.84 Carbon 3.9 524.8 1.06
- a reaction solution containing 100 weight parts of industrial Novolac resin, 12 weight parts of hexamine, 7 weight parts of anhydrous copper(D) sulphate, 190.4 weight parts of ethylene glycol and 33.6 weight parts of monoethanolamine (catalyst and pore former) was gradually heated from 60 to 100° C. in 35-40 minutes. Then the viscous solution was poured in a stream into stirred pre-heated (115-120° C.) mineral oil containing 0.5% of the drying oil. After the initial drop in the resulting emulsion temperature to 110-112° C. further heating was applied at the rate 0.5° C. per minute up to 150° C. Normally cross-lining occurred at 115-120° C.
- FIG. 7 and Table 7 present pore size distributions and some structural parameters of the carbons derived from this resin and containing ca. 5% weight of finely dispersed copper.
- Carbon 7.1 was prepared by heat treatment of the resin at 800° C. in flowing carbon dioxide.
- Reaction solution consisting of 100 weight parts of industrial Novolac resin, 9 weight parts of hexamine, 20 weight parts of boric acid and 258 weight parts of ethylene glycol was heated up from 70 to 100° C. in 45 min. Resulting viscous solution was poured in stream into 3 volumes of stirred preheated (105° C.) oil, containing 0.5% of the drying oil. On further heating curing occurred at around 110° C. Further heating was applied up to 160° C. in 30 min. to complete the curing. After filtering the resin beads off further treatment prior to carbonisation was applied in three different ways:
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- Phenolic Resins Or Amino Resins (AREA)
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Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US11/786,072 US7842736B2 (en) | 2000-08-09 | 2007-04-10 | Porous carbons |
US11/786,074 US20080032092A1 (en) | 2000-08-07 | 2007-04-10 | Porous carbons |
US11/786,073 US20080090924A1 (en) | 2000-08-09 | 2007-04-10 | Porous carbons |
US11/800,805 US7850942B2 (en) | 2000-08-09 | 2007-05-07 | Porous carbons |
US12/459,554 US20100035058A1 (en) | 2000-08-09 | 2009-07-01 | Porous carbons |
US12/913,361 US8591855B2 (en) | 2000-08-09 | 2010-10-27 | Porous carbons |
US13/097,819 US8227518B2 (en) | 2000-08-09 | 2011-04-29 | Porous carbons |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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GB0019417.5 | 2000-08-09 | ||
GBGB0019417.5A GB0019417D0 (en) | 2000-08-09 | 2000-08-09 | Mesoporous carbons |
PCT/GB2001/003560 WO2002012380A2 (en) | 2000-08-09 | 2001-08-07 | Porous carbons |
Related Child Applications (5)
Application Number | Title | Priority Date | Filing Date |
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US11/786,074 Division US20080032092A1 (en) | 2000-08-07 | 2007-04-10 | Porous carbons |
US11/786,073 Division US20080090924A1 (en) | 2000-08-09 | 2007-04-10 | Porous carbons |
US11/786,073 Continuation US20080090924A1 (en) | 2000-08-09 | 2007-04-10 | Porous carbons |
US11/786,072 Division US7842736B2 (en) | 2000-08-09 | 2007-04-10 | Porous carbons |
US11/800,805 Continuation US7850942B2 (en) | 2000-08-09 | 2007-05-07 | Porous carbons |
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US20040024074A1 true US20040024074A1 (en) | 2004-02-05 |
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Family Applications (7)
Application Number | Title | Priority Date | Filing Date |
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US10/344,248 Abandoned US20040024074A1 (en) | 2000-08-07 | 2001-08-07 | Porous carbons |
US11/786,073 Abandoned US20080090924A1 (en) | 2000-08-09 | 2007-04-10 | Porous carbons |
US11/786,072 Expired - Fee Related US7842736B2 (en) | 2000-08-09 | 2007-04-10 | Porous carbons |
US11/786,074 Abandoned US20080032092A1 (en) | 2000-08-07 | 2007-04-10 | Porous carbons |
US11/800,805 Expired - Fee Related US7850942B2 (en) | 2000-08-09 | 2007-05-07 | Porous carbons |
US12/459,554 Abandoned US20100035058A1 (en) | 2000-08-09 | 2009-07-01 | Porous carbons |
US13/097,819 Expired - Lifetime US8227518B2 (en) | 2000-08-09 | 2011-04-29 | Porous carbons |
Family Applications After (6)
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US11/786,072 Expired - Fee Related US7842736B2 (en) | 2000-08-09 | 2007-04-10 | Porous carbons |
US11/786,074 Abandoned US20080032092A1 (en) | 2000-08-07 | 2007-04-10 | Porous carbons |
US11/800,805 Expired - Fee Related US7850942B2 (en) | 2000-08-09 | 2007-05-07 | Porous carbons |
US12/459,554 Abandoned US20100035058A1 (en) | 2000-08-09 | 2009-07-01 | Porous carbons |
US13/097,819 Expired - Lifetime US8227518B2 (en) | 2000-08-09 | 2011-04-29 | Porous carbons |
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AU (1) | AU2001276542A1 (es) |
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WO (1) | WO2002012380A2 (es) |
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Also Published As
Publication number | Publication date |
---|---|
JP6143411B2 (ja) | 2017-06-07 |
JP2004506753A (ja) | 2004-03-04 |
EP2218680A3 (en) | 2015-07-08 |
US7842736B2 (en) | 2010-11-30 |
JP2011168484A (ja) | 2011-09-01 |
US20110237691A1 (en) | 2011-09-29 |
ATE542848T1 (de) | 2012-02-15 |
GB0019417D0 (en) | 2000-09-27 |
JP4834281B2 (ja) | 2011-12-14 |
AU2001276542A1 (en) | 2002-02-18 |
US20080090924A1 (en) | 2008-04-17 |
EP1370605B1 (en) | 2012-01-25 |
US20080032092A1 (en) | 2008-02-07 |
EP1370605A2 (en) | 2003-12-17 |
US20080025907A1 (en) | 2008-01-31 |
US20100035058A1 (en) | 2010-02-11 |
ES2379627T3 (es) | 2012-04-30 |
WO2002012380A2 (en) | 2002-02-14 |
US8227518B2 (en) | 2012-07-24 |
US7850942B2 (en) | 2010-12-14 |
EP2218680A2 (en) | 2010-08-18 |
WO2002012380A3 (en) | 2003-10-09 |
US20100029795A1 (en) | 2010-02-04 |
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