WO2017085278A1 - Partikelförmiges kohlenstoffmaterial herstellbar aus nachwachsenden rohstoffen und verfahren zu dessen herstellung - Google Patents
Partikelförmiges kohlenstoffmaterial herstellbar aus nachwachsenden rohstoffen und verfahren zu dessen herstellung Download PDFInfo
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- WO2017085278A1 WO2017085278A1 PCT/EP2016/078176 EP2016078176W WO2017085278A1 WO 2017085278 A1 WO2017085278 A1 WO 2017085278A1 EP 2016078176 W EP2016078176 W EP 2016078176W WO 2017085278 A1 WO2017085278 A1 WO 2017085278A1
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- TZMQHOJDDMFGQX-UHFFFAOYSA-N hexane-1,1,1-triol Chemical compound CCCCCC(O)(O)O TZMQHOJDDMFGQX-UHFFFAOYSA-N 0.000 description 1
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- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
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- UDKSLGIUCGAZTK-UHFFFAOYSA-N phenyl pentadecane-1-sulfonate Chemical compound CCCCCCCCCCCCCCCS(=O)(=O)OC1=CC=CC=C1 UDKSLGIUCGAZTK-UHFFFAOYSA-N 0.000 description 1
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- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical class [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- 238000002444 silanisation Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
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- TXDNPSYEJHXKMK-UHFFFAOYSA-N sulfanylsilane Chemical class S[SiH3] TXDNPSYEJHXKMK-UHFFFAOYSA-N 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
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- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
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- 230000000930 thermomechanical effect Effects 0.000 description 1
- NBXZNTLFQLUFES-UHFFFAOYSA-N triethoxy(propyl)silane Chemical compound CCC[Si](OCC)(OCC)OCC NBXZNTLFQLUFES-UHFFFAOYSA-N 0.000 description 1
- FBBATURSCRIBHN-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyldisulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSCCC[Si](OCC)(OCC)OCC FBBATURSCRIBHN-UHFFFAOYSA-N 0.000 description 1
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- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical class [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
- C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
- C09C1/44—Carbon
- C09C1/48—Carbon black
- C09C1/56—Treatment of carbon black ; Purification
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
- B60C1/00—Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition
- B60C1/0016—Compositions of the tread
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
- B60C1/00—Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition
- B60C1/0025—Compositions of the sidewalls
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
- B60C5/00—Inflatable pneumatic tyres or inner tubes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/04—Reinforcing macromolecular compounds with loose or coherent fibrous material
- C08J5/0405—Reinforcing macromolecular compounds with loose or coherent fibrous material with inorganic fibres
- C08J5/042—Reinforcing macromolecular compounds with loose or coherent fibrous material with inorganic fibres with carbon fibres
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
- C08K3/013—Fillers, pigments or reinforcing additives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/02—Elements
- C08K3/04—Carbon
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L21/00—Compositions of unspecified rubbers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L97/00—Compositions of lignin-containing materials
- C08L97/005—Lignin
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
- C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
- C09C1/44—Carbon
- C09C1/48—Carbon black
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/002—Inorganic compounds
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10B—DESTRUCTIVE DISTILLATION OF CARBONACEOUS MATERIALS FOR PRODUCTION OF GAS, COKE, TAR, OR SIMILAR MATERIALS
- C10B53/00—Destructive distillation, specially adapted for particular solid raw materials or solid raw materials in special form
- C10B53/02—Destructive distillation, specially adapted for particular solid raw materials or solid raw materials in special form of cellulose-containing material
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2004/00—Particle morphology
- C01P2004/60—Particles characterised by their size
- C01P2004/61—Micrometer sized, i.e. from 1-100 micrometer
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2006/00—Physical properties of inorganic compounds
- C01P2006/12—Surface area
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2006/00—Physical properties of inorganic compounds
- C01P2006/19—Oil-absorption capacity, e.g. DBP values
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2400/00—Characterised by the use of unspecified polymers
- C08J2400/22—Thermoplastic resins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2400/00—Characterised by the use of unspecified polymers
- C08J2400/24—Thermosetting resins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2400/00—Characterised by the use of unspecified polymers
- C08J2400/26—Elastomers
-
- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E50/00—Technologies for the production of fuel of non-fossil origin
- Y02E50/10—Biofuels, e.g. bio-diesel
Definitions
- the present invention relates to a particulate carbonaceous material according to claim 1 and to a process for its preparation according to claim 9 and to the use of the material of claim 19 in polymer blends.
- particulate carbon material There are many applications for particulate carbon material.
- One application is the use as a filler for polymers such as elastomers, thermosets or thermosets.
- fillers are used to improve the rubber properties of the crosslinked rubber articles, e.g. measured as tensile strength, hardness, stiffness or tear strength to influence.
- the product properties such as, for example, vehicle rolling resistance, abrasion and wet skidding behavior are adjusted.
- the influence of rubber-technical properties by a filler is also referred to as reinforcement.
- particulate carbon material which can be used, for example, as a filler and based on renewable raw materials is described, which has surprisingly good properties when used as a filler in elastomers in comparison to the conventionally prepared fillers carbon black and silica.
- a filler is a particulate solid which is added to an elastomer, thermoplastic or thermoset.
- the rubber-technical properties of a (for example by vulcanization) crosslinked rubber mixture by the addition of the filler usually influenced differently with other additives prior to crosslinking.
- a typical filler is silica.
- silica is meant essentially precipitated silica which is mainly used in rubber articles. In addition, there is also the fumed silica.
- Another typical filler is carbon black. This is always meant carbon black, so a technically targeted soot with defined properties. Soot is mainly produced by incomplete combustion or pyrolysis. By soot is meant here no by-products of combustion as in the case of diesel soot or chimney soot.
- the reinforcing effect of carbon black and / or silica correlates strongly with the primary particle size of the filler.
- the primary particle size is directly related to the specific surface area.
- inactive carbon blacks low surface area carbon blacks are referred to as inactive carbon blacks, medium surface carbon blacks as semi-active carbon blacks, and high surface area carbon blacks as active carbon blacks, herein referred to as the degree of reinforcing effect of the respective carbon blacks in the rubber.
- inactive carbon blacks have BET surface areas ⁇ 30 m 2 / g, semi-active carbon black 30-70 m 2 / g and active carbon blacks 90 to> 150 m 2 / g.
- the importance of the surface as a guide is also clear from the fact that the first digit of the ASTM carbon blacks reflects the particle size or the surface. For silica, the differentiation is less pronounced.
- Silica with marked enhancer action typically have BET surface areas> 100 m 2 / g.
- filler is meant a product that achieves at least the performance of an inactive carbon black.
- a performance that is at least comparable to that of an inactive carbon black, is hereinafter also referred to as reinforcing effect.
- a typical inactive carbon black is N990.
- the particle surface is composed of the outer and the inner surface.
- Associated parameter is the specific surface of the particulate material.
- the specific surface can be measured as an outer surface by means of Statistical thickness surface area, abbreviated to STSA, or as a total surface of outer and inner surface by means of nitrogen surface according to Brunauer, Emmett and Teller, BET for short.
- STSA Statistical thickness surface area
- BET Brunauer, Emmett and Teller
- BET surface area minus STSA surface area is a measure of the porosity of finely divided materials as it represents the surface of the pores. The smaller the difference the less porous the material is.For non-porous materials, the BET also describes well the fineness.
- the BET surface area and the STSA surface are determined in accordance with standard ASTM D 6556-14.
- the sample preparation / outgassing for the STSA and BET measurement takes place at 150 ° C.
- STSA Method (Statistical Thickness Surface Area): The evaluation uses the same measurement data as in the BET method, but the measurement is made at higher partial pressures (0.2 to 0.5).
- the STSA method is based on the so-called t-plot evaluation method according to de Boer, later modified by Magee. Here it is assumed that the adsorption takes place locally differently in different stack heights and then have a statistical thickness.
- the STSA surface is also given in m 2 / g and is a measure of the "outer" surface of a soot particle, but above all it is a measure of the rubber-effective surface.
- Soot and silica are composed of primary particles. These geometrical units, which do not exist in isolation but can be seen in pictorial representations, have grown together into aggregates, the adhesion being due to strong chemical bonds.
- aggregates can be aggregated together to form agglomerates, with the connection of several aggregates to agglomerates via weak forces. Agglomerates can be destroyed by dispersion.
- the degree of aggregate formation is outdated by DBP absorption or more recently by oil absorption. Further details can be found in ASTM D 2414. One also speaks of the oil absorption number with the abbreviation OAN for English oil absorption number. A high value of DBP or oil absorption characterizes
- the performance of carbon black or silica in rubber applications is usually determined by measuring rubber characteristics. Rubber characteristics describe certain properties of a rubber compound in the crosslinked, for example, vulcanized state.
- rubber articles are the finished To understand articles made of rubber after their crosslinking or vulcanization. These finished rubber articles are also referred to in the present specification as rubber parts, moldings, articles made of elastomeric material or rubber product. From the wide variety of rubber parts in various applications, there are a variety of different sizes for the description of rubber parts. Depending on the field of application, positive values of a variable elsewhere can also be considered as negative.
- modulus 50% modulus 100%, modulus 200% or modulus 300% As rubber technical parameters are primarily tensile strength (ASTM D 412, DIN 53504), tear strength (DIN 53455) and the stress at 50%, 100%, 200% and 300% elongation (DIN 53504), hereinafter referred to as modulus 50% modulus 100%, modulus 200% or modulus 300% referred used. Furthermore, for example, the hardness (ASTM D 2240) may play a role. For these sizes, high but not too high values are considered positive.
- tan delta is the quotient of the loss modulus E "and the storage modulus E 'of the elastomer material, distinguishing the value of the tan delta in the high temperature range, in particular the tan delta at 60 ° C and the tan delta in the lower temperature range. in particular, the tan delta at 0 ° C. While the tan delta indicates the rolling friction of a tire at 60 ° C, the tan delta is used to assess the wet grip of a tire at 0 ° C. For the tan delta at 60 ° C low values are preferred in this context, high values for the tan delta at 0 ° C.
- the tan delta values are determined by means of a dynamic mechanical analysis (temperature sweep)
- the dynamic mechanical analysis (DMA) becomes prismatic in the case described here Dimensions of 2x10x35 mm for the temperature variation performed on an Eplexor 150N Dynamic Mechanical Thermal Spectrometer.
- Untreated silica is a filler with polar functional groups that can interfere with cross-linking in sulfur-crosslinked systems.
- the disruption of sulfur crosslinking may be due, for example, to the adsorption of vulcanization aids to the polar functional groups of the filler surface.
- the different surface energies of polymer and filler prevent a good dispersion of the filler in the polymer and at a reheating of the mixture (eg in the vulcanization) to an undesirable re-agglomeration of the already dispersed filler particles result (so-called Grestoffflokkulation). This is the starting point for the addition of reagents to the silica.
- the polar groups of the silica are reacted with suitable basic compounds, whereby these groups are deactivated or masked.
- the silica as such in its entirety is activated in this way in its function as reinforcing filler, ie the surface chemistry of the silica is adapted by this activation or masking to the surface chemistry of the polymer. See: Fritz Röthemeier, Franz Sommer, 3rd edition, Carl Hanser Verlag Kunststoff 2013 on page 301 - 302. To improve the rubber properties, silica is generally used with coupling reagents.
- Coupling reagents are bifunctional compounds which, on the one hand, attach to the silica and, on the other hand, to the rubber, thus creating a bond between the silica and the rubber. This is particularly important since silica and rubber are inherently incompatible chemically.
- a typical coupling agent is bis (triethoxypropylsilyl) tetrasulfide when using silica in rubber.
- adhesion promoters are used, which also provide for a bond between polymer and another component, which may be another polymer or a filler.
- coupling agent is also understood to mean an adhesion promoter.
- the grain size or the particle size distribution is often indicated. This is mainly determined by laser diffraction or sieve analysis. It is usually stated either what percentage of the number (Q0 distribution) or the volume (Q3 distribution) of particles of a certain geometric extension of the total amount of particles has. The indication is usually in ⁇ .
- the particle size covers the size of the particle present under the specific conditions. It depends on the dispersing medium and the dispersion quality. The particle size does not distinguish between particles as a result of macroscopic caking, for example by foreign substances, particles as a result of microscopic agglomeration in the case of insufficient dispersing effort or particles in the form of isolated aggregates or primary particles. It indicates the extent of an externally limited body, even if it may consist of several connected parts. By means of the material density (bulk density), the mass distribution can be calculated from the volume distribution.
- the morphology of fillers may be fibrous, platy or spherical.
- the length-to-diameter ratio can be used.
- the expansions in different spatial directions are determined, for example, by means of electron microscopic measurements (TEM, SEM).
- TEM electron microscopic measurements
- the aspect ratio the quotient of the largest and smallest extent. It can be specified both in the form x: y and in the form of the calculated quotient.
- a sphere would have an aspect ratio of 1, ellipsoidal structures of about 1.5 to 2 and fiber-like structures over 10.
- soot which is produced from raw materials of fossil origin, ie based on coal tar, natural gas or crude oil hereinafter referred to as classic carbon black.
- Raw materials of fossil origin are above all all derived from petroleum substances, such as distillates, distillation residues or processed by cracking petroleum ingredients. Also included among the fossil raw materials are all products obtained in the distillation, coking or liquefaction of lignite, coal or anthracite.
- Natural gas is also a fossil resource. All fossil carbon sources have in common that their 14 C content is below that of renewable raw materials because they no longer participate in the constant isotope exchange.
- renewable resources are all products derived from the direct use of plants or animals. If one thinks of the soot production process, these can be primarily vegetable oils or animal fats. In the broader sense, and thus in the sense of this document, any biomass counts.
- Biomass are all organic substances that are accessible from the use of plants or animals or that are generated as waste of this use; including derived or separated derived products and wastes. Without limiting it here, wood, straw, sugar, starch, vegetable oil, leaves, peels, bagasse, empty fruit stands, fermentation residues, green waste or organic municipal waste can be cited as typical biomass forms. It is common to call organic material that has a shorter regeneration time than peat biomass. Specifically, this includes waste from the industrial use of plants. For example, large amounts of wood are processed in the pulp industry where lignin-containing wastes such as black liquor are produced. All biomass have in common that their 14 C content is above that of fossil resources, as they participate in the steady isotope exchange.
- a biomass species is lignin, which is obtained in some wood processing processes.
- Lignin is a naturally occurring polymer, which can be derived primarily from the basic building blocks coumaryl, coniferyl and sinapyl alcohol.
- KRAFT lignin usually dissolved in black liquor, hydrolysis lignin or lignin sulfonate.
- the hydrogen atoms in the typical lignin-type hydroxyl groups may be proportionally replaced by metal cations.
- the lignosulfonate is actually a chemical derivative of lignin, as it has additional sulfonate groups added during processing.
- HTC is the abbreviation for hydrothermal carbonation. This is the treatment of a substance in aqueous phase under pressure and at elevated temperature. Due to the increased pressure, it is possible to carry out reactions in liquid water in which the temperature is well above 100 ° C, ie above the boiling point of water at atmospheric pressure.
- Fillers having a reinforcing effect are used according to the prior art predominantly for improving the rubber properties of rubber articles.
- the two most common fillers for rubber applications are carbon black and silica. Soot is extracted almost exclusively from fossil fuels. Since the product according to the invention is a e.g. Particulate carbon material which can be used as a filler and is obtained from renewable raw materials is not part of the state of the art for the classic carbon blacks obtained from fossil raw materials. Silica is a filler derived from inorganic silicon compounds. Therefore, silicas are also not state of the art.
- carbon black can also be produced from renewable raw materials.
- the disclosed carbon black is said to be a filler in especially narrower ones Aggregate size distribution above all have an improved modulus in rubber applications.
- the carbon blacks characterized in WO 2010/043562 A1 are in the range of the classic carbon blacks N220 and N375 in terms of their basic properties.
- the soot described here is produced in the classic Furnace process, whereby natural gas is used in a pre-combustion chamber and the release of fossil carbon occurs.
- the so obtained carbon black has an S content of max. 2.5%, a volatile matter content according to DI N 53552 of max. 2.5% on and thus roughly a C content of more than 95% carbon.
- WO 2014/096544 A1 claims a carbon product which is formed from porous carbon particles having a surface area of more than 500 m 2 / g and an average pore volume of less than 1 ml / g, which in turn comprises primary particles, such as aggregates, exist, which have a particle size of less than 250 nm.
- the carbon product is obtained from hydrothermal carbonization of bio-material that has more than 40% carbon to dry weight.
- lignin, tannin and betulin, hydrolysis lignin, products from the production of paper, plates, biofuel or brewing products are mentioned.
- the carbon content of the products described in the examples is between 77.31 and 86.44% carbon.
- the strong carbonization of the material indicated in the examples means that other elements, such as especially oxygen and hydrogen, must be depleted. This inevitably leads to the disadvantage that the surface chemistry of the material is depleted, that is, there are less functional groups on the surface. The lower surface groups have a detrimental effect on possible attachment mechanisms to the polymer. It is also known to use renewable raw materials such as lignin or lignin derivatives both without and with coupling reagents in rubber mixtures directly to influence the rubber properties in the crosslinked state.
- DE 10 2008 050 966 A1 describes a rubber mixture containing a lignin derivative, more particularly a ligninsulfonic acid derivative, up to alkali or alkaline earth salts of lignosulfonic acid.
- the rubber composition prepared using this Ligninsulfonklaivats may also contain carbon black or silica.
- the application also claims a tire from the aforementioned rubber compound.
- a disadvantage is, as the examples disclosed in DE 10 2008 050 966 A1 show that the lignin derivatives are always used in addition to 40 phr of carbon black or 80 phr of silica / 5 phr of carbon black.
- silica is used in this document for silicic acid. Thus, only an improvement of the rubber technical parameters in combination with the classic fillers is achieved.
- the use of renewable raw materials in rubber mixtures with the aid of coupling reagents makes particular use of knowledge in the use of silica.
- silica it is generally known that in sulfur-crosslinked systems fillers having polar functional groups, such as e.g. untreated silicic acid that interfere with cross-linking. At the same time it is known that this disorder can be mitigated by adding suitable reagents such as amines or glycols. The functional groups are blocked or masked. See: Fritz Röthemeier, Franz Sommer, 3rd edition, Carl Hanser Verlag Kunststoff 2013 on page 301 - 302.
- silica reinforcement it is known that the effect of silica on coupling reagents can be significantly improved.
- functional alkoxysilanes are used which, on the one hand, can bind to the silica upon mixing with the alkoxysilane group to form an Si-O-Si bond and later bind to the rubber polymer with a further function in the vulcanization, if appropriate with the aid of added sulfur.
- Suitable reinforcing white fillers are silicic acid and silicates.
- silane as a coupling reagent in renewable resources to be used as fillers are known.
- EP 2 223 928 A1 describes a functionalized lignin, wherein groups contained in the lignin react with functionalizing agents and these reagents may be anhydrides, esters and silanes. Furthermore, a rubber mixture is disclosed which contains functionalized lignin as a filler, optionally mixed with conventional carbon black or silica and optionally a coupling reagent for the functionalized lignin or for the silica.
- HTC hydrothermal carbonization
- WO 2014/122163 A1 discloses a method for producing carbon-enriched biomass material, the resulting biomass material, and describes its use.
- the feedstock lignocellulosic material is treated at elevated temperature, preferably at a maximum of 120-320 ° C, and partially oxidizing conditions, ie at substoichiometric presence of oxygen preferably in the range 0.15-0.45 mol / kg dry lignocellulosic material, and after opening In the reactor, solid products are optionally separated from the reaction mixture.
- the feed has a moisture content between 10% and 70% and a size between 0.2 and 100 mm.
- the applied pressure is between 1 and 100 bar absolute.
- the reaction time is given as 2-500 min.
- the carbon concentration is increased by 8 - 25%.
- the material obtained has a maximum of 45-60% carbon, besides 5-8% hydrogen and 35-50% oxygen. As a use, only the combustion, especially in the ground state for dust firing is specified.
- a method for obtaining carbonized lignin having a defined grain size distribution from a lignin-containing liquid wherein the lignin-containing liquid is subjected to hydrothermal carbonization, whereby the lignin is converted into a carbonized lignin, and the carbonized lignin from the carbonated lignin-containing Liquid is separated, the lignin-containing liquid is subjected to a hydrothermal carbonization at temperatures in the range of about 150 ° C to about 280 ° C and the grain size distribution of the carbonized lignin by adjusting the H + ion concentration in the lignin-containing liquid before and / or during the hydrothermal carbonization is set.
- the adjustment of the H + ion concentration of a lignin-containing liquid can influence the distribution of the grain size of the obtained product, ie the size of the agglomerates.
- a particulate carbon material preparable from renewable raw materials in particular from lignocellulosic biomass, has the following features: a 14 C content which corresponds to that of renewable raw materials, preferably greater than 0.20 Bq / g carbon, particularly preferably greater than 0 , 23 Bq / g carbon, but preferably less than 0.45 Bq / g carbon;
- OAN oil absorption number
- lignocellulosic biomass and in particular lignocellulosic biomass with a proportion of klason lignin of more than 80% are preferably used as the renewable raw material (for the determination of the lignin content, the Klason process is used in which the polysaccharides are replaced by a biomass two-stage acid hydrolysis degraded and the remaining lignin residue is then weighed as Klason lignin).
- Lignin is a byproduct of woody biomass fractionation processes.
- the lignin is typically either solubilized and then separated from the non-soluble constituents of the woody biomass (eg KRAFT process) or the woody biomass is depolymerized so that the lignin remains predominantly as a solid (eg hydrolysis process). Accordingly, depending on the type of fractionation process, the lignin is either dissolved in a lignin-containing liquid, for example black liquor, or as a generally mechanically dewatered solid. If the lignin is dissolved in a liquid containing the lignin, the lignin can usually be precipitated therefrom, for example using acids or acidic gases, and recovered as a mechanically dewatered solid (compare, for example, the LignoBoost process).
- the 14 C content which corresponds to that of renewable raw materials, distinguishes the present particulate carbon material, which can be used, for example, as a filler in elastomers, thermosets or thermosetting plastics, from classic carbon black based on fossil raw materials.
- the particulate carbon material has a 14 C content of greater than 0.20 Bq / g of carbon, particularly preferably greater than 0.23 Bq / g of carbon, but preferably in each case less than 0.45 Bq / g of carbon.
- the carbon content based on the ashless dry matter of more than 60% by mass and less than 80% by mass, preferably more than 65% by mass and less than 75% by mass, more preferably more than 68% by mass and less than 74% by weight, moreover preferably more than 70% by weight and less than 73% by weight distinguishes the present filler which can be used particulate carbon material of renewable raw materials used as filler, such as wood flour, etc., which typically have a lower carbon content.
- the carbon content based on the ashless dry matter of more than 60% by mass and less than 80% by mass distinguishes the present particulate carbon material from products made from renewable raw materials, for example by fractionation, extraction, distillation or crystallization, such as sugar, starch, Cellulose, etc., which typically have a lower carbon content based on the ashless dry matter of 40% by mass to 50% by mass.
- the present particulate carbon material differs from lignin which has been separated from biomass by a KRAFT process, which typically has a carbon content based on the ashless dry matter of 65 mass%.
- the carbon content based on the ashless dry matter of more than 60% by mass and less than 80% by mass also distinguishes the present particulate carbon material from conventional carbon black produced according to the usual carbon black production processes or the variants of bio-based carbon blacks both via the usual Rußher einhussclar but also for example via pyrolysis, partial oxidation, carbonization or similar processes are prepared, which typically have a higher carbon content based on the ashless dry matter of about 95% and more. Even in the case of highly oxidized carbon blacks containing 950 ° C. according to DIN 53552 of 20% and additionally 2.5% sulfur, the carbon content, based on the ashless dry matter, is approximately 88%.
- the advantage of the low carbon content of the present product compared with carbon black is that the surface functionality resulting from the renewable raw materials is partly retained and can be utilized in the application, for example via coupling reagents.
- the STSA surface area of at least 5 m 2 / g and at most 200 m 2 / g, preferably between 8 m 2 / g and 100 m 2 / g further distinguishes the present particulate carbon material from non-porous lignin or non-porous particulate material over the hydrothermal carbonation, which usually has BET surface areas of less than 2 m 2 / g, with the - usually not measured - STSA surfaces are naturally slightly lower.
- the present particulate carbon material differs therefrom from particulate materials of renewable resources having a high specific BET surface area due to their high porosity, such as pyrolysis carbons, coals recovered via partial oxidation, coals recovered via hydrothermal carbonation and activated carbons in that the particulate carbon material present is substantially non-porous and very finely divided, which is detected by the STSA surface.
- the STSA surface has values between 10 m 2 / g and 80 m 2 / g, preferably between 12 m 2 / g and 70 m 2 / g, more preferably between 15 m 2 / g and 70 m 2 / g, particularly preferably between 20 m 2 / g and 70 m 2 / g.
- the BET surface area of the present particulate carbon material differs only by a maximum of 20%, preferably by a maximum of 15%, more preferably by a maximum of 10%, from the STSA surface.
- the pore volume of the particulate carbon material is ⁇ 0.1 cm 3 / g, more preferably ⁇ 0.01 cm 3 / g, particularly preferably ⁇ 0.005 cm 3 / g.
- the present particulate carbon material differs from finely divided porous materials such as ground biogenic powdered activated carbon, which in addition to a BET surface area of more than 500 m 2 / g may also have an STSA surface area of not more than 10 m 2 / g.
- the advantage of the high STSA surface compared to lignin and HTC carbon is the high fineness of the product, which allows a high degree of interaction between the present product and eg polymers.
- Advantage of almost nonexistent Porosity of the present product is that, for example, compared to the use of porous carbon materials, additives and crosslinking chemicals can not lose their effectiveness by penetrating the pores.
- the average size of the primary particles of the particulate carbon material is advantageously limited to a value greater than 8 nm, preferably greater than 10 nm, more preferably greater than 15 nm.
- the primary particles of the particulate carbon material have a heterogeneous size distribution.
- the smaller particle fraction accordingly has a size of greater than 8 nm, preferably greater than 10 nm, more preferably greater than 15 nm, up to a size of 250 nm.
- the larger particle fraction has sizes above 250 nm.
- primary particles are grown into aggregates, whereby the size of the primary particles differs from the size of the aggregates.
- the size of the primary particles is below 250 nm.
- the primary particles are smaller than aggregates, preferably by an average of at least a factor of 2, more preferably by an average of at least a factor of 4.
- primary particles can be present individually and then theoretically equated with aggregates. In this preferred embodiment, however, this is only rarely, preferably less than 25%, more preferably less than 20%, most preferably less than 15% of the case. This is especially true for primary particles larger than 250 nm in size.
- the OAN value is between 65 ml / 100 g and 150 ml / 100 g, more preferably between 70 ml / 100 g and 130 ml / 100 g, moreover preferably between 75 ml / 100 g and 130 ml / 100 g , especially preferably between 80 ml / 100g and 120 ml / 100g.
- OAN absorption is determined according to ASTM D 2414-00.
- the advantage of the high oil absorption number over carbon products with lower oil adsorption number is the presence of aggregates which have an advantageous effect on the interactions between the present particulate carbon material and, for example, polymers.
- the present particulate carbon material has a water content of less than 5% by mass, preferably less than 3% by mass, more preferably less than 2% by mass.
- the present low water content or the dry state of the carbon material allows its incorporation, e.g. as a filler in polymers because generation of vapor bubbles at high temperature is avoided.
- increased humidity of the carbon material is troublesome for the use of coupling reagents.
- a 15% suspension of the particulate carbon material in distilled water has an electrical conductivity of less than 5 mS / cm, preferably less than 3 mS / cm, and more preferably less than 2 mS / cm.
- the electrical conductivity (determined as the conductance of the measuring probe of the PCE-PHD1 device at 20 ° C. to 25 ° C.) is used here as a measure of the ion content or the ion concentration, in particular of ions selected from the group containing Na + , Ca 2 + , S0 4 2 " , CO3 2" , S 2 " , HS " .
- Advantage of the low Leiêt is the low proportion of water-soluble ions, which could also be separated when used for example in polymers of the present product.
- an embodiment of the particulate carbon material in a 15% suspension in distilled water has a pH of> 6, preferably> 7, more preferably> 8.
- the pH of a 15% suspension of the particulate carbon material in distilled water is less than 10, more preferably less than 9.
- the advantage of the neutral or slightly basic pH of the present product, for example, is its good compatibility with the others Components of the polymer mixture.
- the present particulate carbon material has a D / G signal ratio in the Raman spectrum between 0.20 and 0.90, preferably between 0.40 and 0.75, more preferably between 0.45 and 0.70 as a measure of the proportion of graphitic carbon.
- the area ratio D / G of the D band to the G band in the Raman spectrum can be used.
- the D-band is above 1300 cm-1 to about 1360 cm-1 and the G-band (graphite band) is about 1580-1590 cm-1.
- the integrals of the Raman spectrum are calculated by the D-band and the G-band and then put into proportion.
- the material can be used in some applications - due to its share of graphitic carbon - as a classic soot and beyond - due to its share of amorphous carbon and the elements bonded to it - more Functionalities are available.
- the present particulate carbon material has low solubility in basic solution.
- the present particulate carbon material advantageously has a high resistance to bases.
- a high resistance to bases means that less than 40%, preferably less than 30%, particularly preferably less than 15%, in particular less than 10% of the particulate carbon material present goes into solution.
- the following procedure is preferably used to determine the base stability:
- the percent base strength is determined by dividing the dry weight of the weighed residue by the dry weight of the particulate carbon material weighed and multiplying by 100.
- the solubility of the particulate carbon material in percent is determined by subtracting the base stability of 100.
- the particulate carbon material of lignin of the invention differs in that its resistance to bases is markedly increased.
- This has the advantage that the present particulate carbon material is e.g. in the case of use as a filler in rubber products or plastic products on contact with water from the rubber product or plastic product is not easily washed out.
- the particulate carbonaceous material according to the invention has a surface chemistry comparable to silica.
- a silica-comparable surface chemistry it is meant that the present carbon material has high OH group density.
- the oxygen content of the present ashless particulate carbonaceous material is between 20 mass% and 30 mass%, preferably between 20 mass% and 25 mass%.
- the present particulate carbon material differs from carbon black, which is obtained, for example, by intensive carbonization (pyrolysis, oxidation, hydrothermal carbonation, etc.) from renewable resources, characterized in that the functional groups of the renewable raw materials used to produce the present particulate carbon material not by the thermal treatment has been largely separated, but continue to be available for attachment to polymers or coupling reagents available.
- carbon black which is obtained, for example, by intensive carbonization (pyrolysis, oxidation, hydrothermal carbonation, etc.) from renewable resources, characterized in that the functional groups of the renewable raw materials used to produce the present particulate carbon material not by the thermal treatment has been largely separated, but continue to be available for attachment to polymers or coupling reagents available.
- the ash content of the particulate carbon material based on the dry matter is at least 1% by mass but less than 8% by mass, more preferably at least 2% by mass and less than 6% by mass, moreover preferably at least 3% by mass and less than 6% by mass, in particular at least 4% by mass and less than 6% by mass (ash content in accordance with DIN 51719 at 815 ° C.).
- the D90 of the particle size distribution (as a measure of the size of the particles present under the specific conditions) is less than 30 ⁇ m, preferably less than 20 ⁇ m, more preferably less than 15 ⁇ , more preferably less than 10 ⁇ , especially at less than 5 ⁇ .
- the D99 of the Q3 particle size distribution is less than 30 ⁇ m, preferably less than 20 ⁇ m, more preferably less than 15 ⁇ m, more preferably less than 10 ⁇ m, in particular less than 5 ⁇ m ⁇ .
- the D99 of the Q3 distribution of the particle size at more than 1 ⁇ m is preferably more than 2 ⁇ m.
- the present particulate carbon material when used for example in polymers caused by the maximum size of the separated particles causes no impurity, which for example premature cracking or breaking of the polymer or Surface defects in the extrusion lead.
- the average ball diameter determined with the aid of the STSA surface is advantageously at least 2 times, preferably at least 3 times, more preferably at least 4 times, in particular at least 6 times smaller, assuming a material density (bulk density) of 1500 kg / m 3 as the average diameter (D50) of the separated particle measured via the Q3 distribution of the grain size.
- the average ball diameter is calculated using the following formulas:
- the measurement of the particle size distribution of the particulate carbon material is carried out in a 10% suspension with distilled water by means of laser diffraction. Before and / or during the measurement of the particle size distribution, the sample to be measured is dispersed with ultrasound until a particle size distribution which is stable over several measurements is obtained.
- the STSA surface of the present particulate carbon material is preferably substantially independent of its Q3 distribution of grain size and characterizes the fineness of the primary particles.
- the present particulate carbon material has a 14 C content equal to that of renewable resources, preferably greater than 0.20 Bq / g of carbon, more preferably greater than 0.23 Bq / g of carbon, but preferably less than 0.45 Bq / g carbon;
- the particulate carbonaceous material of the present invention has a shape which substantially conforms to the shape of classical carbon black.
- a form of the present particulate carbon material comparable to classic carbon black is given, for example, by the particulate carbon material
- the present u.a. filler-formable particulate carbonaceous material of prior art fillers obtained, for example, by refining renewable resources, characterized in that the filler has a distinct structure comparable to that of classical carbon blacks.
- the shape can be determined, for example, by SEM images.
- the particulate carbon material which can be used as a filler preferably has a non-fibrous morphology, by which is meant that the aspect ratio is less than 10, preferably less than 5.
- the present particulate carbon material has a 14 C content equal to that of renewable resources, preferably greater than 0.20 Bq / g of carbon, more preferably greater than 0.23 Bq / g of carbon, but preferably less than 0.45 Bq / g of carbon;
- a carbon content in relation to the ashless dry matter of more than 60% by mass and less than 80% by mass;
- this preferred embodiment of the present particulate carbon material has a similar potential for filler-polymer interactions as a classic carbon black and allows for this interaction potential additionally via a similar mechanism as with silicic acid eg supplemented by coupling reagents.
- the particulate carbon material may be used, for example, as a filler or reinforcing filler.
- the particulate carbon material according to the invention can be used, for example, in rubber and rubber mixtures or plastic.
- polymer blends which are characterized in that they contain at least one polymer and at least one particulate carbon material according to the invention.
- Polymers can be thermoplastics, thermosets or elastomers.
- polymers are selected from a list of the following plastics or rubbers: polyester, polyethylene, polypropylene, polyestercarbonates, polyamides, polyimides, polyesteramides, polyetherimides, polyurethanes, polyvinyl alcohols, polyvinyl acetates, polyvinyl chlorides, polymethacrylates, polystyrenes, styrene-maleic anhydride, polycaprolactones, polybutylene terephthalates, polyepoxides ; Cellulose products such as cellulose acetate or cellulose nitrate, vulcanized fiber, polylactic acid, polyhydroxyalkanoates, chitin, casein, gelatin; Formaldehyde resins such as melamine-formaldehyde resin, urea-formaldehy
- the particulate carbon material may be used in amounts of from 10 mass% to 150 mass%, preferably 20 mass% to 120 mass%, more preferably 40 mass% to 100 mass%, most preferably 50 mass% .-% to 80 wt .-%, based on the mass of the rubber used, are used.
- the rubber mixture preferably contains at least the particulate carbon material according to the invention and, in addition, naturally occurring mineral, siliceous, chalky or calcareous fillers.
- the rubber mixture preferably contains the particulate carbon material according to the invention and a coupling reagent, preferably an organosilane.
- the organosilanes can be, for example, bis (trialkoxysilylalkyl) -oligo- or -poly-sulfide, for example bis (triethoxysilylpropyl) disulfide or bis (triethoxysilylpropyl) tetrasulfide, mercaptosilanes, aminosilanes, silanes with unsaturated hydrocarbon groups, for example vinylsilanes.
- silanes with large saturated hydrocarbon groups for example, dodecyltriethoxysilane, can act as coupling reagents, but with no covalent bonds, but rather van der Waals forces provide some coupling to the polymer.
- the organosilane is preferably used in amounts of 2% by mass to 16% by mass, more preferably 4% by mass to 14% by mass, particularly preferably 6% by mass to 12% by mass, based on the weight of the particulate carbon material used.
- selected rubber characteristics are achieved in the crosslinked state of the rubber mixture, which are comparable to those obtained using a Half-active carbon black or a silica can be achieved together with an organosilane.
- selected rubber-technical characteristics are preferably not only achieved but also exceeded in the crosslinked state of the rubber mixture, which are achieved when using a carbon black having an STSA surface comparable to that of the particulate carbon material.
- the rubber mixture contains the particulate carbon material according to the invention and a reagent masking the functional groups, preferably an organosilane, an amine or a glycol.
- a reagent masking the functional groups preferably an organosilane, an amine or a glycol.
- the amine for example, triethanolamine, hexamethylenetetramine, di-o-tolylguanidine or diphenylguanidine can be used.
- glycol ethylene glycol, tetraethylene glycol or polyethylene glycol can be used.
- the organosilane may be a trialkoxysilylalkylsilane, for example triethoxymethysilane, triethoxyethysilane or triethoxypropylsilane.
- the reagents mentioned are not able to be incorporated into the cross-linking via sulfur bridges. However, they react with the surface of the carbon material according to the invention with consumption of the functional groups, so that they affect the sulfur crosslinking less. Thus, the triethoxyalkyl silanes do not act as a coupling reagent. However, in addition to avoiding disrupted sulfur crosslinking, such silanes act as compatibilizers which match the surface energy of the filler particles to those of the polymer matrix, thus resulting in significantly improved dispersibility.
- carbon black in a rubber compound can be substituted for up to 100% by the particulate carbonaceous material present and still achieve comparable performance in the crosslinked state as with the carbon black in terms of selected rubber characteristics.
- silicic acid in a rubber mixture can be substituted by up to 100% by the particulate carbon material present and, nevertheless, comparable performance can be achieved in the crosslinked state as with silicic acid with regard to selected technical rubber properties, an organosilane being preferably used.
- Preferred rubber-technical characteristics are the modulus 50% and modulus 200% determined in the tensile test. Preferred are high values for the modulus 50% and modulus 200%.
- Another preferred rubber technical characteristic is the loss factor tan delta (quotient of loss modulus E "and storage modulus E 'of the elastomer material) at temperatures between 40 ° C., preferably 50 ° C., more preferably 60 ° C. and 100 ° C.
- This characteristic value is a common predictor value for the rolling friction in the tire industry, preferred are low values for the tan delta in the given temperature range, more preferably the tan delta depression is at least 10% over the carbon black reference, especially The tan delta reduction is preferably at least 15% higher than the carbon black reference
- Additional preferred rubber characteristic value is the loss factor tan delta at 0 ° C. determined in a dynamic mechanical analysis (temperature sweep)
- This characteristic value is a common predictive value for the wet grip in the tire industry, with high values for tan delta 0 ° C
- the tan delta increase is at least 10% higher than the carbon black reference.
- the rubber mixture contains in a preferred embodiment, in addition to the particulate carbon material also carbon blacks, preferably contain semi-active carbon blacks or active carbon blacks.
- This rubber mixture preferably contains at least the particulate carbon material, at least one carbon black preferably a semi-active carbon black or an active carbon black and naturally occurring mineral, silicate, calcareous or calcareous fillers.
- This rubber mixture preferably contains at least the particulate carbon material, at least one carbon black preferably a semi-active carbon black or an active carbon black and naturally occurring mineral, silicate, calcareous or calcareous fillers and at least one organosilane.
- the advantage of the simultaneous use of the particulate carbon material together with a carbon black is that certain rubber technical characteristics of the vulcanized rubber compound can be improved.
- the rubber mixture preferably contains not only the particulate carbon material according to the invention but also silicic acids, preferably precipitated and pyrogenic silicic acids, and may furthermore contain naturally occurring, mineral, siliceous, chalky or calcareous fillers and an organosilane.
- Synthetic rubbers are suitable for the preparation of the rubber mixtures according to the invention in addition to natural rubber (NR). Preferred synthetic rubbers are described, for example, in W. Hofmann, Kautschuktechnologie, Genter Verlag, Stuttgart 1980 or in WO 2010/043562 from page 15, line 4 to page 15, line 24.
- SBR styrene-butadiene copolymers
- BR polybutadiene
- NBR acrylonitrile-butadiene copolymers
- Chloroprene fluoro rubber or acrylic rubber and mixtures thereof.
- the rubber mixtures according to the invention may comprise further rubber auxiliaries, such as reaction accelerators, anti-aging agents, heat stabilizers, light stabilizers, antiozonants, processing aids, plasticizers, tackifiers, blowing agents, dyes, pigments, waxes, extenders, organic acids, retarders, metal oxides and activators, such as diphenylguanidine, triethanolamine, polyethylene glycol alkoxy-terminated polyethylene glycol or hexane triol known to the rubber industry.
- rubber auxiliaries such as reaction accelerators, anti-aging agents, heat stabilizers, light stabilizers, antiozonants, processing aids, plasticizers, tackifiers, blowing agents, dyes, pigments, waxes, extenders, organic acids, retarders, metal oxides and activators, such as diphenylguanidine, triethanolamine, polyethylene glycol alkoxy-terminated polyethylene glycol or hexane triol known to the rubber industry.
- Crosslinkers which can be used are sulfur, organic sulfur donors or free-radical formers.
- the rubber mixtures according to the invention may additionally contain vulcanization accelerators.
- the blending of the rubbers with the particulate carbon material, optionally carbon blacks, optionally silicas, optionally rubber auxiliaries and optionally organosilanes can be carried out in conventional mixing units, such as rolling mills, internal mixers and mixing extruders.
- conventional mixing units such as rolling mills, internal mixers and mixing extruders.
- such rubber mixtures are produced in the internal mixer, wherein the rubbers, the particulate carbon material, optionally carbon black, optionally silica, optionally rubber adjuvants and optionally organosilanes are mixed at 100 ° C to 170 ° C in one or more successive thermomechanical mixing stages.
- the order of addition and the time of addition of the individual components can have a decisive effect on the mixture properties obtained.
- the rubber mixture thus obtained is then usually mixed in an internal mixer or on a rolling mill at 40-120 ° C with the crosslinking chemicals and processed to form the so-called raw mixture for the subsequent process steps, such as molding and vulcanization.
- the vulcanization of the rubber mixtures according to the invention can be carried out at temperatures of 80 ° C to 200 ° C, preferably 130 ° C to 180 ° C, optionally under pressure of 10 to 200 bar.
- the rubber mixtures according to the invention are suitable for the production of rubber articles, ie articles from the fully crosslinked or vulcanized elastomers, so-called moldings, for example for the production of pneumatic tires, tire treads, tire sidewalls, cable jackets, hoses, drive belts, conveyor belts, roller coverings, tires, shoe soles, buffers, Sealing rings, profiles and damping elements.
- plastic mixtures which are characterized in that they contain at least one plastic and at least one particulate carbon according to the invention.
- Plastic in this context means a thermoplastic or thermosetting plastic.
- the particulate carbon material may be used in amounts of 10% by mass to 150% by mass, preferably 20% by mass to 120% by mass, more preferably 30% by mass to 100% by mass, based on the mass of used plastic, are used.
- the plastic mixture preferably contains the particulate carbon material according to the invention and an adhesion promoter or a coupling reagent.
- the adhesion promotion is based on the use of maleic anhydride or other organic acids, preferably unsaturated carboxylic acids.
- adhesion promoters it is also possible, for example, to use silanes, preferably with particularly large hydrocarbon radicals, for example triethoxydodecylsilane.
- the adhesion promoter is preferably used in amounts of 2% by mass to 16% by mass, more preferably 4% by mass to 14% by mass, particularly preferably 6% by mass to 12% by mass, based on the composition used of the plastic used.
- Plastics may be, for example, polyethylene (PE), polypropylene (PP), polyvinyl acetate (PVA) or thermoplastic elastomers (TPE).
- the plastic mixtures according to the invention are preferably used for the production of cables, pipes, fibers, films, in particular agricultural films, engineering plastics and injection-molded articles.
- the present particulate carbon material is prepared in a process according to the invention, which in particular allows the adjustment of the STSA surface area and the OAN value to the range given above.
- a multistage, in particular four-stage, process for the hydrothermal treatment, in particular carbonization of renewable raw materials, in particular of renewable raw materials with a content of more than 80% Klason lignin is provided by
- a liquid containing the renewable raw material is provided,
- Raw material in the liquid containing the renewable raw material the pH of the liquid containing the renewable raw material, the concentration of inorganic ions in the liquid containing the renewable raw material,
- a STSA surface of at least 5 m 2 / g and a maximum of 200 m 2 / g and an OAN value of at least 50 ml / 100g and a maximum of 150ml / 100g is set.
- the conductance of the liquid containing the renewable raw material is used instead of the concentration of the inorganic ions of the liquid containing the renewable raw material.
- the STSA surface area and the OAN value of the particulate carbonaceous material obtained in the fourth step are obtained by mutual agreement
- the desired STSA surface is adjusted by increasing the temperature of the hydrothermal treatment and / or prolonging the residence time in the hydrothermal treatment with a desired increase in the STSA surface area.
- the temperature of the hydrothermal treatment is increased and / or the residence time in the hydrothermal treatment is prolonged when the yield of dry particulate carbon material is very low, preferably less than 10%, more preferably less than 20%, moreover preferably less than 30%, particularly preferably less than 40%, in each case based on the dry mass of the renewable raw material.
- the STSA surface area and the OAN value of the particulate carbonaceous material obtained in the fourth step are obtained by mutual agreement
- Raw material in the liquid containing the renewable resource the pH of the liquid containing the renewable resource, the concentration of inorganic ions in the renewable
- the concentration of the organic dry matter of the renewable raw material in the liquid containing the renewable resource increased and / or
- the pH of the liquid containing the renewable raw material is lowered and / or
- the concentration of inorganic ions in the liquid containing the renewable resource is increased.
- the desired STSA surface is adjusted by lowering the temperature of the hydrothermal treatment and / or shortening the residence time in the hydrothermal treatment with a desired lowering of the STSA surface.
- temperature and residence time is meant not only the maximum temperature, which is maintained over a certain residence time, but the temperature-time profile, which is passed through in the second step. If, in the following, no temperature-time profile is indicated, however, the temperature is meant to be the maximum temperature which is maintained over a certain residence time. Temperature and dwell time are also referred to collectively below as process conditions.
- the present method has the advantage over the prior art that the formation of the desired finely divided particles is not already completed in the first step, but only during the hydrothermal treatment in the second step conditions are brought to the formation of the particulate carbon material with corresponding STSA Surface and OAN value. Only by such a procedure, it becomes possible, at the same time a particle formation and a reaction As a result, this leads to a particulate carbon material which, for example, also differs from the renewable raw material used in terms of its carbon content or its resistance to bases.
- the concentration of the organic dry matter of the renewable raw material in the liquid containing the renewable raw material in the liquid containing the renewable raw material, the pH of the liquid containing the renewable raw material, the concentration of inorganic ions in the liquid containing the renewable raw material,
- the polymerization of the renewable raw material in the second step is largely suppressed or limited so that a particulate carbon with a corresponding STSA surface area and OAN value is obtained, and the particle size distribution.
- the size distribution of the agglomerates or particles separated under certain conditions can be directly influenced to the size of the primary particles which is detected by the STSA surface.
- the build-up of porosity in the material is suppressed, as evidenced by a small difference between the STSA surface area and the BET surface area of the particulate carbon material. Preference is given to recruitment and mutual coordination
- the concentration of the organic dry matter of the renewable raw material in the liquid containing the renewable raw material in the liquid containing the renewable raw material, the pH of the liquid containing the renewable raw material, the concentration of inorganic ions in the liquid containing the renewable raw material,
- the STSA surface area and the OAN value of the particulate carbonaceous material obtained in the fourth step are adjusted
- Raw material in the liquid containing the renewable raw material preferably to a value between 5 wt .-% and 40 wt .-%, more preferably between 10 wt .-% and 20 wt .-%,
- the pH of the liquid containing the renewable raw material at 20 ° C to 25 ° C preferably to a value> 7, more preferably> 8, particularly preferably> 8.5, more preferably ⁇ 1 1,
- the concentration of inorganic ions in the liquid containing the renewable raw material preferably at a value between 10 mS / cm and 200 mS / cm, preferably between 10 and 150 mS / cm, more preferably between 10 and 50 mS / cm, more preferably between 10 and 40 mS / cm, particularly preferably between 10 mS / cm and 25 mS / cm (determined as conductance of the probe of the PCE-PHD 1 at 20 ° C to 25 ° C), the temperature of the hydrothermal treatment preferably to a maximum value between 200 ° C and 250 ° C, preferably to a maximum value between 210 and 245 ° C and / or
- the residence time in the hydrothermal treatment is preferably controlled to a duration of between 1 minute and 6 hours, preferably between 30 minutes and 4 hours, particularly preferably between 1 hour and 3 hours, and thus an STSA surface area between 5 m 2 / g and 200 m 2 / g and an OAN value between 50 ml / 100g and 150ml / 100g.
- the renewable raw material in the first step is completely dissolved in the liquid containing the renewable resource.
- the renewable raw material is not completely dissolved in the liquid containing the renewable resource in the first step, but
- the advantage of the complete solution of the renewable raw material in the liquid containing the renewable raw material is that a solid-solid transition is suppressed and the solid which can be separated off in the third step is completely formed from the solution, ie a transition from the solution to the solid takes place.
- the process is operated continuously, wherein the process conditions of the hydrothermal treatment are kept constant in the second step and a continuous adjustment of the pH and the conductance of the liquid contained in the renewable raw material in the first step, to fluctuations in the quality of the renewable raw material compensate.
- This approach has the advantage that the much more complex setting of the process conditions in the second step can be avoided.
- the temperature and the residence time in the second step are adjusted so that to achieve an STSA surface between 5 m 2 / g and 200 m 2 / g and an OAN value between 50 ml / 100g and 150 ml /100 g
- Ions can be made by addition of salts until the matching to the process conditions of the second stage concentration of inorganic ions, measured over the conductance, is reached.
- This approach has the advantage that the conductance can be used to fine tune the quality of the liquid containing the renewable resource, as it can be measured much easier and more reliable than the pH.
- the concentration of the organic dry matter of the renewable raw material is adjusted in the liquid containing the renewable raw material, the pH of the liquid containing the renewable raw material and / or the concentration of inorganic ions in the liquid containing the renewable raw material in the second step.
- the renewable raw material in the liquid containing the renewable raw material is advantageously completely dissolved in the first step and the formation of the desired finely divided particles during the hydrothermal treatment in the second step not only by the selected process conditions but also by increasing the concentration the organic dry matter of the renewable raw material in the liquid containing the renewable resource, a reduction in the pH of the liquid containing the renewable resource or an increase Hung of the concentration of inorganic ions in the liquid containing the renewable raw material brought about.
- the advantage of such a process control is that the conditions which lead to the formation of the desired finely divided particles can be specifically brought about in the second step, thereby increasing the stability of the process and optionally reducing the residence time in the second step.
- the concentration of the dry organic matter in the liquid containing the particulate carbon material it is advantageous to lower the concentration of the dry organic matter in the liquid containing the particulate carbon material, increase the pH of the liquid containing the particulate carbon material, or lower the concentration of inorganic ions in which the particulate carbon material containing liquid causes. This advantageously takes place already in the second step or at the latest in the third step.
- This procedure ensures that, upon completion of the formation of the desired particulate material, no further solid is produced, for example during the cooling phase at the end of the second step or by increasing the concentration of the dry organic matter in the liquid containing the particulate carbon material, for example by evaporation in the third Step is formed.
- the pressure corresponds at least to the saturated steam pressure of the liquid containing the renewable raw material.
- the concentration of organic dry matter of a lignin-containing liquid in the first step is between 10% by mass and 20% by mass
- the pH of the lignin-containing liquid in the first step is more than 8.5 and less than 10.5,
- the residence time of the lignin-containing liquid in the hydrothermal treatment in the second step between 120 and 240 minutes by
- the STSA surface area of the thus obtained particulate carbon material measured after dehydration in the third step and drying in the fourth step has a value between 5 m 2 / g and 50 m 2 / g and an OAN value between 50 ml / 100 g and 100 ml / 100g.
- the process according to the invention may further comprise a laundry following the dehydration in the third step or a pulverization following the drying in the fourth step.
- the drying in the fourth step is preferably carried out at temperatures below the softening point of the particulate carbon material, preferably at temperatures below 150 ° C., more preferably at temperatures below 130 ° C.
- the D90 of the Q3 distribution of the particle size of the particulate carbon material after drying in the fourth step by pulverization to a value less than 30 ⁇ , preferably less than 20 ⁇ , more preferably less than 15 ⁇ particularly preferably less than 10 ⁇ adjusted.
- the process is carried out in particular without the addition of a co-polymerizable compound or a polymerization initiator and without fermentation of the biomass.
- Figure 1 is a diagram of the stress-strain curve in the tensile test as an example of the rubber technical characteristics of crosslinked rubber articles from SBR with the particulate carbon material according to the invention and of the associated reference.
- Figure 2 is a diagram of the curves of the loss factor tan delta (logarithmic
- Figure 3 is a graph of the stress-strain curve in the tensile test as a comparison of the rubber characteristics of crosslinked rubber articles from SBR, with the untreated lignin, with the particulate carbon material according to the invention but without coupling reagent and with the Particulate carbon material and coupling reagent according to the invention are provided.
- Figure 4 is a graph of the stress-strain curve in the tensile test as a comparison of the rubber characteristics of crosslinked rubber articles from SBR, with the particulate carbon material according to the invention but without further additive, with the particulate carbon material according to the invention and a reagent for masking the functional groups and with the particulate inventive Carbon material and a coupling reagent are provided.
- Figure 5 is a graph of the stress-strain curve in the tensile test as a comparison of the rubber technical characteristics of articles of Elastomerwerkstoff- mixtures based on natural rubber and butadiene NR / BR and the particulate carbon material in each case with different mixing procedures and from the reference.
- Figure 6 is a graph of the stress-strain curve in the tensile test as a comparison of the rubber technical characteristics of crosslinked rubber articles made of NBR, which are provided with the particulate carbon material according to the invention without coupling reagent and the reference.
- the exemplary embodiments describe the process according to the invention for obtaining the particulate carbonaceous material according to the invention, its properties and its performance in the crosslinked rubber.
- a liquid containing the renewable resource is provided.
- water (1) and lignin (2) are mixed and a lignin-containing liquid having an adjusted content of organic dry matter (3) is prepared.
- the lignin is then completely dissolved in the lignin-containing liquid.
- the pH is adjusted to the desired value by adding a base or an acid (6) (7).
- the solution is prepared by intensive mixing in a suitable temperature (4) for sufficient time (5).
- a certain concentration of inorganic ions is set, which is measurable as conductivity (9).
- the composition and properties of the lignin-containing liquid thus prepared are shown in Table 1,
- composition of the lignin used is shown in Table 2.
- the liquid containing the renewable raw material is subjected to a hydrothermal treatment to obtain a solid.
- the solution prepared in the first step is heated from a starting temperature (10) over a heating time (1 1) to a reaction temperature (12) which is maintained over a reaction time (13). Subsequently, cooling takes place over a cooling time (14) to a final temperature (15). As a result, a solid is obtained.
- the pH (16) and the conductivity (17) of the liquid containing the solid vary.
- the pH and the concentration of inorganic ions in the first step and appropriate choice of process conditions in the second step set in the second step conditions in which the particulate carbon material in a crude form of the Solution separates.
- the process conditions of the second step are listed in Table 3.
- the crude particulate carbon material is dewatered and optionally washed.
- the crude particulate carbon material is largely separated from the liquid containing it by dehydration (18). Subsequently, the crude particulate carbon material is washed with a multiple of mass of water and dehydrated again (19).
- Table 4 The process conditions of the third step are summarized in Table 4.
- the dehydrated crude particulate carbon material and remaining liquid are dried at elevated temperature (20, see Table 5), thereby obtaining the particulate carbon material. Subsequently, the particulate carbon material can be de-agglomerated (21, see Table 5).
- the carbon materials obtained according to the embodiments 1 and 2 are introduced as a filler in a rubber compound and vulcanized with the aid of further additives.
- the composition of the rubber compound is shown in Table 7.
- SBR used was solution SBR (sSBR) Buna VSL 4526-0 HM from Lanxess. It is a copolymer of 26% by mass of styrene in addition to butadiene. Its Mooney viscosity is 65 ME (ASTM D 1646). Zinc oxide, stearic acid and sulfur were from Fischer Scientific. 2-N-cyclohexyl benzothiazolesulfenamide (CBS) was from Lanxess. 1,3-Diphenylguanidine (DPG) was used by Sigma-Aldrich Co. LLC, USA. The process oil TDAE (VIVATEC 500) was from Klaus Dahleke KG.
- SBR solution SBR (sSBR) Buna VSL 4526-0 HM from Lanxess. It is a copolymer of 26% by mass of styrene in addition to butadiene. Its Mooney viscosity is 65 ME (ASTM D 1646). Zinc oxide, stearic acid
- the antioxidant 2,2,4-trimethyl-1,2-dihydroquinoline polymer TMQ was supplied by CH Erbslöh, Krefeld. N- (1,3-dimethylbutyl) -N'-phenyl-P-phenylenediamine (6PPD) was purchased from GmbH & Co. KG, Düsseldorf. As coupling was used bis (triethoxysilylpropyl) tetrasulfide, which is sold under the name Si69 ® from Evonik Industries.
- SBR was presented in the internal mixer (Haake Rheomix 600P, ThermoFisher Scientific, Düsseldorf) at 145 ° C and a filling factor of 0.7, corresponding to 56 cm 3 volume. Subsequently, the fillers were added in two stages. After optional addition of silane Si69 For complete silanization, the temperature in the internal mixer was kept in a range between 140-165 ° C for 10 minutes and mixed at a speed of 60 min -1 .
- antioxidants and vulcanization additives were carried out on a two-roll mill (Polymix-1 10L, Servitec Maschinen Service GmbH, Wustermark) at a starting temperature of 50 ° C and a constant friction of 1: 1 .2.
- the rubber compounds reference and A are crosslinked using a usual for the application of carbon black vulcanization process.
- the rubber compounds B, C and D (Table 7) are crosslinked using a vulcanization process common to the use of silica together with Si69.
- the samples were vulcanized in a laboratory press TP1000 (Fontijne Grotnes B.V., Viaardingen Netherlands) at 160 ° C and a pressing force of 150 kN.
- the optimal vulcanisation time tgo was determined by means of a Rubber Process Analyzer (Scarabaeus SIS-V50, Scarabaeus GmbH, Wetzlar).
- Examples B, C and D (in which a coupling reagent is added) comparable properties as the filler N660.
- the values for the modulus 50%, modulus 100% and modulus 200% of examples B and C are at least as high as for the reference.
- the increase of the degree of filling from 40 phr (B) to 60 phr (D) of the particulate carbon material according to Example 2 at elongation in the lower range (up to 100%) leads to an increase of the voltage values, ie the modulus 50% and Modulus 100%, leads.
- the loss factor tan delta (quotient of loss modulus E "and storage modulus E 'of the elastomer material) as a function of the temperature, determined in a dynamic mechanical analysis (temperature sweep), is shown in Figure 2 and Table 8.
- the tan delta curves are close to each other, although the curve of the reference mixture from about 76 ° C is slightly lower than that of Example 12 A and thus indicates a slightly lower energy loss.
- Example 12 B The use of the particulate carbon material of Example 2 in combination with a coupling reagent (Example 12 B) leads to significant changes.
- the energy loss properties of mixture 12 B are significantly improved compared to the reference with N660, which is visible at the lower curve in the temperature range above the glass transition temperature.
- the elastomeric material containing the particulate carbon material of Example 2 and a coupling reagent has lower values than the N 660 for tan delta reference above the glass transition temperature, suggesting a relatively reduced rolling friction in a tire of this material.
- untreated lignin was already used in rubber mixtures.
- the following comparative example shows the differential effect of untreated lignin and the carbon material according to the invention in a rubber compound.
- Lignin 3 from Table 2 is introduced as a filler in a rubber mixture for comparison purposes and vulcanized with the aid of further additives.
- the composition of the rubber compound corresponds to the composition in Example 12 B, but instead of the particulate carbon material from Example 2 now untreated lignin 3 is used.
- the rubber composition for Example 13 is crosslinked using a conventional vulcanization process for the use of silica together with Si69. The stress-strain curve in a tensile test as an example of the rubber properties of the resulting rubber article is shown together with the results of Example 12 A and 12 B in the diagram of Figure 3.
- Example 14 for determining the 14 C content of the product from Example 2
- Example 2 The material of Example 2 was added to the Poznah Radiocarbon Laboratory, Foundation of A. Mickiewicz University, ul. Rubiez 46, 61-612 Poznah for determination of the 14 C content. The method used is described by the head of the laboratory Tomasz Goslar on the website of the institute. The essential content of lignin is summarized below.
- the analysis shows the age of the carbon sample for archaeological purposes.
- the measurement result can also be specified as a specific activity.
- the specific activity analysis gave a value of 243.30 ⁇ 0.52 Bq / kgC or Bq / kg of carbon.
- Example 15 for the production of rubber articles from SBR with the particulate carbon material of Example 2 in the presence of a functional group masking reagent:
- the carbon material obtained according to embodiment 2 is introduced as a filler in a rubber compound and vulcanized with the aid of further additives.
- the Composition of the rubber compound and its processing corresponds to that in Example 12 B (Table 7), however, replacing the silane Si69 equimolar with triethoxymethylsilane, which corresponds to an employment of 1, 06 phr. Further processing is analogous to Example 12.
- the triethoxymethylsilane is unable to be incorporated into the network via sulfur bridges. However, it reacts with the surface of the carbon material according to the invention with consumption of the functional groups.
- the functional groups reacting with the silane are replaced externally by methyl groups, which leads to compatibilization of the filler surface with the nonpolar rubber matrix compared to the unmodified starting material.
- the triethoxymethylsilane-treated carbon material of the present invention provides a higher tensile strength in rubber than the carbon material used without silane, but is expected to lag behind the carbon material in combination with the coupling silane Si69.
- the stress-strain curve in a tensile test as an example of the rubber properties of the obtained rubber articles in Figure 4 shows that it may be useful in selected rubber systems and for selected applications to perform a masking of the functional groups.
- the carbon material obtained according to Example 2 is introduced as a filler in a mixture of NR and BR and vulcanized with the aid of further additives.
- a mixture (pre-mix) of NR and BR is first prepared in the internal mixer (Haake Rheomix 600P, ThermoFisher Scientific, Düsseldorf) at a starting temperature of 120 ° C., which is then mixed with the respective filler and further constituents is offset.
- the internal mixer starting temperature 35 ° C, speed 60 min -1
- first a masterbatch of BR, the filler and silane produced is then further processed with NR and the remaining constituents (also in the internal mixer, Starting temperature 120 ° C, speed 60 min -1 ).
- the quantity composition of both processing variants is identical.
- the stress-strain curve in a tensile test as an example of the rubber properties of the obtained rubber articles from Examples A and B are shown in the diagram of FIG. These show that in NR / BR mixtures the carbon material according to the invention can be used for reinforcement. Furthermore, it can be seen that the order of processing has an influence on the performance of the filler in the articles of the respective NR / BR rubber compound in the crosslinked state. In this way, modulus and tensile strength can be influenced.
- the carbon material obtained according to Example 4 is introduced as a filler in NBR and vulcanized with the aid of further additives but without coupling reagent.
- the composition of the rubber compound is shown in Table 9.
- Table 9 The mixtures are prepared on a Haake Rheomix 600 (tangential rotor geometry, 78 cm 3 ) with an initial temperature of 40 ° C and a rotor speed of 100 min -1 . There are first 2 min the NBR polymer, then 2 min additional stearic acid, ZnO, optionally material from Example 4 and talcum, further 4 min additionally optionally N990 and Mesamoll II, another 3 min antioxidants and a further 2 min the vulcanization mixed. The optimum cure time was determined by a Rubber Process Analyzer and the mixture vulcanized at 160 ° C for a minute value of (tgo + 1 / mm layer thickness).
- the hardness Shore A was determined according to DIN 53505: 2000-08, the tensile test according to DIN 53504: 2009-10 and the storage for 72 h at 70 ° C in oil Lubrizol OS 206304 according to DIN ISO 1817: 2008-08].
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Abstract
Description
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Priority Applications (23)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
HRP20230719TT HRP20230719T1 (hr) | 2015-11-21 | 2016-11-18 | Čestice ugljičnog materijala iz obnovljivih sirovina |
ES16809654T ES2949315T3 (es) | 2015-11-21 | 2016-11-18 | Material de carbono en forma de partículas producible a partir de materias primas renovables |
LTEPPCT/EP2016/078176T LT3377585T (lt) | 2015-11-21 | 2016-11-18 | Kietųjų dalelių anglies medžiaga iš atsinaujinančių žaliavų |
FIEP16809654.3T FI3377585T3 (en) | 2015-11-21 | 2016-11-18 | SMALL PARTICLE COAL MATERIAL FROM RENEWABLE RAW MATERIALS |
EP20160400.6A EP3682965B1 (de) | 2015-11-21 | 2016-11-18 | Verfahren zu herstellung von partikelförmigem kohlenstoffmaterial aus nachwachsenden rohstoffen |
CN202210133009.4A CN114395275A (zh) | 2015-11-21 | 2016-11-18 | 由可再生原材料制备的颗粒状的碳材料和用于其制备方法 |
KR1020187017579A KR20180083932A (ko) | 2015-11-21 | 2016-11-18 | 재생 가능한 원료로부터 제조될 수 있는 미립자 탄소 물질 및 상기 탄소 물질의 제조 방법 |
CA3002724A CA3002724C (en) | 2015-11-21 | 2016-11-18 | Particulate carbon material producible from renewable raw materials and method for its production |
EP16809654.3A EP3377585B1 (de) | 2015-11-21 | 2016-11-18 | Partikelförmiges kohlenstoffmaterial aus nachwachsenden rohstoffen |
DK16809654.3T DK3377585T3 (da) | 2015-11-21 | 2016-11-18 | Partikelformigt kulstofmateriale af fornyelige råstoffer |
BR112018008961-3A BR112018008961B1 (pt) | 2015-11-21 | 2016-11-18 | Material de carbono particulado que pode ser produzido a partir de matérias-primas renováveis e processo para sua produção |
US15/777,906 US11312864B2 (en) | 2015-11-21 | 2016-11-18 | Particulate carbon material producible from renewable raw materials and method for its production |
JP2018526521A JP6934867B2 (ja) | 2015-11-21 | 2016-11-18 | 再生可能な原料から製造することができる微粒子状炭素材料、およびその製造方法 |
BR122020009058-8A BR122020009058B1 (pt) | 2015-11-21 | 2016-11-18 | Processo em etapas múltiplas para o tratamento hidrotérmico de matérias-primas renováveis |
SI201631717T SI3377585T1 (sl) | 2015-11-21 | 2016-11-18 | Ogljikov material v obliki delcev iz obnovljivih surovin |
PL16809654.3T PL3377585T3 (pl) | 2015-11-21 | 2016-11-18 | Materiał węglowy w postaci cząstek z surowców odnawialnych |
CN201680068049.8A CN108291098A (zh) | 2015-11-21 | 2016-11-18 | 能由可再生原材料制备的颗粒状的碳材料和用于其制备方法 |
RU2018121627A RU2729689C2 (ru) | 2015-11-21 | 2016-11-18 | Зернистый углеродный материал, получаемый из возобновляемого сырья |
EP22150185.1A EP4006112A1 (de) | 2015-11-21 | 2016-11-18 | Mischungen, insbesondere kautschukmischungen, enthaltend aus nachwachsenden rohstoffen herstellbares partikelförmiges kohlenstoffmaterial und verwendung davon |
US16/847,523 US11639444B2 (en) | 2015-11-21 | 2020-04-13 | Hydrothermal treatment of renewable raw material |
US17/468,246 US11306209B2 (en) | 2015-11-21 | 2021-09-07 | Particulate carbon material producible from renewable raw materials and method for its production |
US17/468,253 US20210403723A1 (en) | 2015-11-21 | 2021-09-07 | Particulate Carbon Material Producible From Renewable Raw Materials And Method For Its Production |
US17/585,004 US20220145085A1 (en) | 2015-11-21 | 2022-01-26 | Particulate Carbon Material Producible From Renewable Raw Materials And Method For Its Production |
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