EP4334396A1 - Biogenes schwarzpigment, verfahren zu seiner herstellung und seine verwendung - Google Patents
Biogenes schwarzpigment, verfahren zu seiner herstellung und seine verwendungInfo
- Publication number
- EP4334396A1 EP4334396A1 EP22727864.5A EP22727864A EP4334396A1 EP 4334396 A1 EP4334396 A1 EP 4334396A1 EP 22727864 A EP22727864 A EP 22727864A EP 4334396 A1 EP4334396 A1 EP 4334396A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- biogenic
- mass
- black pigment
- pigment
- less
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
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- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229920005573 silicon-containing polymer Polymers 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000002341 toxic gas Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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
-
- 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
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K9/00—Use of pretreated ingredients
- C08K9/04—Ingredients treated with organic substances
- C08K9/06—Ingredients treated with organic substances with silicon-containing compounds
-
- 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
- C09C3/00—Treatment in general of inorganic materials, other than fibrous fillers, to enhance their pigmenting or filling properties
- C09C3/006—Combinations of treatments provided for in groups C09C3/04 - C09C3/12
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- 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
- C09C3/00—Treatment in general of inorganic materials, other than fibrous fillers, to enhance their pigmenting or filling properties
- C09C3/04—Physical treatment, e.g. grinding, treatment with ultrasonic vibrations
- C09C3/041—Grinding
-
- 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
- C09C3/00—Treatment in general of inorganic materials, other than fibrous fillers, to enhance their pigmenting or filling properties
- C09C3/12—Treatment with organosilicon compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
- C09D11/037—Printing inks characterised by features other than the chemical nature of the binder characterised by the pigment
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/32—Inkjet printing inks characterised by colouring agents
- C09D11/324—Inkjet printing inks characterised by colouring agents containing carbon black
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/60—Additives non-macromolecular
- C09D7/61—Additives non-macromolecular inorganic
- C09D7/62—Additives non-macromolecular inorganic modified by treatment with other compounds
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2004/00—Particle morphology
- C01P2004/51—Particles with a specific particle size distribution
-
- 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
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- C01—INORGANIC CHEMISTRY
- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2006/00—Physical properties of inorganic compounds
- C01P2006/60—Optical properties, e.g. expressed in CIELAB-values
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- 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
- C01P2006/60—Optical properties, e.g. expressed in CIELAB-values
- C01P2006/62—L* (lightness axis)
-
- 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
- C01P2006/60—Optical properties, e.g. expressed in CIELAB-values
- C01P2006/63—Optical properties, e.g. expressed in CIELAB-values a* (red-green axis)
-
- 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
- C01P2006/60—Optical properties, e.g. expressed in CIELAB-values
- C01P2006/64—Optical properties, e.g. expressed in CIELAB-values b* (yellow-blue axis)
-
- 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
- C01P2006/80—Compositional purity
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- 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
- C08K2201/00—Specific properties of additives
Definitions
- Biogenic black pigment process for its production and its use
- the present invention relates to a biogenic black pigment.
- the present invention relates to a method for producing the biogenic black pigment.
- the present invention relates to the use of the biogenic black pigment.
- Carbonaceous charred materials were used for cave drawings as early as the Stone Age. The technical requirements for such materials were low, a more or less black shade was sufficient.
- Soot was needed for the production of leather paint, paints, printer's ink, inks and car grease.
- soot Instructions for making soot can be found in Codex latinus Monacensis 4 one around the year Manuscript created in 1470 in the Tegernsee dormitor. In order to produce particularly fine soot for special applications, tree resins in particular were burned with a limited supply of air. Until the 16th century, this was the only known process for producing soot with the smallest particle sizes comparable to carbon black. This process is still used today under the name flame black process. From the 19th century, soot was increasingly extracted from natural gas and coal tar.
- a further disadvantage is that the content of acidic surface oxides on the pigment blacks has to be increased by means of an oxidative post-treatment in order to make them processable. Nitrogen dioxide, nitric acid or ozone are used as the oxidizing agent.
- Carbon powders are also available on the market. These carbon powders consist e.g. of pyrolyzed oak wood, coconut shells or hemp materials. These materials have a large particle size distribution and low color strength. In the discolorations, e.g. in PVC-p, clear specks appear due to large particles. With the exception of powdered coconut charcoal, all of these materials are more or less brown in color or have a bluish or gray tinge, such as oak charcoal, graphite flakes, pine charcoal or vine charcoal (supplier: Werth-Metall, Arnplant Str. 21, 99096 Erfurt). These materials are unusable as pigments.
- the Chinese manufacturer Spec Chem Industry Inc. (Shilin Industrial Park, No.10 Wanshou Road, Jiangbei New Area, Nanjing, PR. China) (www.specchemind.com) offers carbon black pigments made from bamboo, wood, coconut shells, Oak wood and food-grade vegetables can be produced by pyrolysis at 1000°C.
- the grain sizes of the SpecKare®BCP pigment are between 2500 nm and 5000 nm (2.5 pm to 5 pm).
- the pigments are used in face and body cleansers, dental care, mud packs, cakes, cookies and ice cream.
- SpecKare® BCP is very weak in color and not suitable for technical coloring of plastic materials.
- the present invention was based on the object of producing a biogenic black pigment from renewable materials which has a deep black hue, high color strength, good dispersibility, a low PAH value and a low heavy metal content.
- the biogenic black pigment is said to be outstandingly suitable for the achromatic coloring and tinting of plastics, plastic parts, coating materials, printing inks, inks, paints, paper, cardboard, cardboard, and mineral materials, and as a reinforcing filler for rubber-like, thermoplastic, liquid-crystalline, and magnetorheological elastomers.
- “Renewable materials” are also referred to below as renewable raw materials or biomass.
- biogenic black pigment according to the invention according to independent patent claim 1 was found.
- Advantageous embodiments of the biogenic black pigment according to the invention are the subject matter of dependent claims 2 to 6.
- the biogenic black pigment of the invention had a deep black hue, high color strength, good dispersibility, a low PAH value and a low heavy metal content.
- the biogenic black pigment is ideal for the achromatic coloring and tinting of plastics, plastic parts, coating materials, printing inks, inks, paints, paper, cardboard, cardboard and mineral materials, as well as reinforcing fillers for rubber-like, thermoplastic, liquid-crystalline and magnetorheological elastomers.
- biogenic black pigment according to the invention was not toxic due to its particularly low content of polycyclic aromatic hydrocarbons (PAH) and its particularly low content of heavy metals, which was below the respective limit values.
- PAH polycyclic aromatic hydrocarbons
- the advantageous properties of the biogenic black pigment according to the invention and thus also the method according to the invention for its production can be attributed to the fact that the black pigment was slightly polar because it had a carbon content of ⁇ 95% by mass and a Oxygen content> 5% by mass.
- the black pigment was slightly polar because it had a carbon content of ⁇ 95% by mass and a Oxygen content> 5% by mass.
- the advantageous properties of the biogenic black pigment according to the invention and thus also the method according to the invention for its production can be attributed to the fact that the black pigment was not obtained from the gas phase, but was obtained from a biogenic raw material by precipitation followed by pyrolysis.
- the inventive method by a special biogenic, particulate Carbon material went out as the starting product, delivered the desired advantageous end product in high yield and in an excellently reproducible manner.
- the special, biogenic, particulate carbon material made it possible to carry out the pyrolysis during the method according to the invention in a comparatively short time at comparatively low temperatures, which is why the method according to the invention was particularly energy-efficient compared to other pyrolysis methods.
- the special, biogenic, particulate carbon material allows the biogenic black pigment obtained from it to be outstandingly suitable for achromatic coloring and chromatic tinting.
- a further advantage was that the starting product of the process according to the invention itself represents a product of value that can be produced easily and can also be used in a variety of ways, so that it was always available in sufficient quantities. This made the process of the invention, and thus the biogenic black pigments of the invention, particularly economical.
- biogenic black pigment of the invention could be put to numerous uses, the diversity of which was surprising. This advantageously distinguished the biogenic black pigment of the invention from conventional, commercially available carbon blacks and black pigments.
- biogenic black pigments according to the invention also had particular application advantages.
- the biogenic black pigment according to the invention has a 14 C content of greater than 0.20 Bq/g carbon, particularly preferably greater than 0.23 Bq/g carbon, but less than 0.45 Bq/g carbon, preferably less than 0.40 Bq /g carbon.
- the 14 C content is determined using the radiocarbon method in accordance with DIN EN 16640:2017-08.
- biogenic in the context of the present invention means that the black pigment according to the invention can be obtained from renewable raw materials and is therefore not obtained from fossil raw materials.
- the biogenic black pigment of the invention has a proportion of volatile components, determined according to DIN 51720, based on the dry matter of the pigment, of 20% by mass to 40% by mass. This is preferably at least 22.5% by mass. This is preferably at most 35% by mass, more preferably at most 30% by mass.
- the dry matter of the black pigment according to the invention is accordingly the anhydrous pigment.
- the biogenic black pigment according to the invention preferably has a proportion of volatile components, determined in accordance with DIN EN 53552, based on the dry mass of the pigment, of 20% by mass to 40% by mass. This is preferably at least 25% by mass. This is preferably at most 35% by mass, more preferably at most 30% by mass.
- the volatile fraction of the black pigment according to the invention can thus be determined both in accordance with DIN 51720 and in accordance with DIN EN 53552.
- the biogenic black pigment according to the invention preferably has a proportion of so-called fixed carbon, based on the dry mass of the pigment, of 60% by mass to 80% by mass. This is preferably at least 65% by mass, more preferably at least 65.5% by mass. This is preferably at most 75% by mass, more preferably at most 72.5% by mass.
- the proportion of fixed carbon, based on the dry mass of the pigment is calculated as follows: 100 wt D1506-15 (550°C), based on the dry weight of the pigment.
- the biogenic black pigment according to the invention has a mass fraction of carbon, determined according to DIN 51732, based on the dry mass of the pigment, of more than 60% by mass, preferably more than 65% by mass, more preferably more than 70% by mass. , particularly preferably more than 75% by mass, particularly preferably more than 77.5% by mass.
- the proportion by mass of carbon, based on the dry mass is preferably less than 95% by mass, more preferably less than 94% by mass, even more preferably less than 93% by mass more preferably less than 90% by mass, particularly preferably less than 87.5% by mass, more preferably less than 85% by mass.
- the biogenic black pigment according to the invention preferably has a mass fraction of oxygen, based on the ash-free dry mass, of more than 5% by mass, preferably more than 7.5% by mass, more preferably more than 8% by mass, particularly preferably more than 9% by mass, particularly preferably more than 10% by mass, but preferably less than 20% by mass, preferably less than 17.5% by mass, particularly preferably less than 15% by mass % more preferably less than 12.5% by mass.
- the mass fraction of oxygen, based on the ash-free dry matter is calculated as follows: 100% by mass minus carbon content minus hydrogen content minus nitrogen content minus sulfur content, with the carbon content, hydrogen content and nitrogen content being determined according to DIN 51732 and the sulfur content according to DIN 51724- 3 is determined.
- the ash-free dry matter is determined according to ASTM D1506-15 (550°C).
- the ash-free dry mass can be calculated from the difference between the dry mass determined according to DIN 51718 and the ash content determined according to ASTM D1506-15 (550°C).
- the biogenic black pigment according to the invention has an ash content, determined according to ASTM D1506-15 (550° C.), based on the dry mass of the pigment, of more than 0.5% by mass, preferably more than 1% by mass and less than 7% by mass, preferably less than 6% by mass, preferably less than 5% by mass, particularly preferably less than 4% by mass.
- the biogenic black pigment according to the invention has preferably been modified by means of at least one additive, preferably at least partially on its surface.
- the biogenic black pigment according to the invention also preferably has a mass fraction of at least one additive for modifying, in particular for partial depolarization, the pigment surface of 1.0% by mass to 10% by mass, based in each case on the dry mass of the pigment. This means the mass fraction after the modification has taken place. It should be noted here that, depending on the additive used, elimination products such as alcohols can be formed during the modification, which then do not contribute to the aforementioned mass fraction.
- the mass fraction is preferably less than 8% by mass, more preferably less than 6% by mass.
- the at least one surface modification additive is preferably selected from the group consisting of silanes, siloxanes and alkylammonium salts of copolymers with acidic groups, and mixtures thereof.
- An example of a suitable additive based on Alkyl ammonium salts of copolymers is BYK®-9076 from Altana.
- An example of a suitable additive based on organofunctional silanes is 3-aminopropyltrimethoxysilane (GENIOSIL® GF 96 from WACKER).
- the biogenic black pigment according to the invention has a mass fraction of polycyclic aromatic hydrocarbons (PAH), based on the dry mass of the pigment, of less than 10 ppm.
- PAH polycyclic aromatic hydrocarbons
- the content of polycyclic aromatics was determined according to FDA Method 63 according to 21 CFR Sec 178.3297:1994-07 in connection with MAS_PA036:2013-12 and MAS_PA017:2016-09.
- the sum of the 22 PAHs is preferably less than 10 ppm, more preferably less than 8 ppm, particularly preferably less than 5 ppm.
- the sum of the 7 GS-PAK is preferably less than 10 ppm, more preferably less than 5 ppm, particularly preferably less than 2 ppm.
- the sum of the 18 GS-PAH is preferably less than 10 ppm, more preferably less than 8 ppm, particularly preferably less than 5 ppm.
- the mass fraction of benzo[a]pyrene, benzo[e]pyrene, benzo[a]anthracene, benzo[b]fluoranthene, benzo[j]fluoranthene, benzo[k]fluoranthene or dibenzo[a,h]anthracene is preferably included in each case less than 2.0 ppm, more preferably less than 1.0 ppm, more preferably less than 0.5 ppm, in particular less than 0.25 ppm, in some cases less than 0.2 ppm.
- the biogenic black pigment according to the invention has a mass fraction of lead, mercury, cadmium and chromium, based on the dry matter of the pigment, of less than 100 ppm, preferably less than 50 ppm, particularly preferably less than 25 ppm, determined according to DIN EN ISO 11885 and based on the dry matter , on.
- the biogenic black pigment according to the invention preferably has a mass fraction of manganese, determined according to DIN EN ISO 11885 and based on the dry mass, of more than 10 ppm and less than 100 ppm.
- the biogenic black pigment of the invention has an STSA according to ASTM standard D6556 of 5 m 2 /g to 200 m 2 /g, preferably 10 m 2 /g to 150 m 2 /g, preferably 15 m 2 /g to 150 m 2 /g , particularly preferably 20 m 2 /g to 120 m 2 /g and in particular 20 to 80 m 2 /g.
- the biogenic black pigment according to the invention preferably has a BET according to ASTM standard D6556, which is preferably at least 10% greater than the STSA.
- the BET is preferably at least 25 m 2 /g, more preferably at least 30 m 2 /g, more preferably at least 50 m 2 /g, also preferably at least 100 m 2 /g, moreover preferably at least 150 m 2 /g g, more preferably at least 200 m 2 /g, more preferably at least 250 m 2 /g.
- the BET is at most 500 m 2 /g, preferably at most 400 m 2 /g, more preferably at most 350 m 2 /g, in particular at most 300 m 2 /g.
- the BET is preferably 5 m 2 /g, more preferably 10 m 2 /g, more preferably 20 m 2 /g, particularly preferably 50 m 2 /g, in particular 100 m 2 /g, further preferably 150 m 2 /g, in embodiments 200 m 2 /g higher than the STSA.
- the BET is preferably no more than 400 m 2 /g, more preferably no more than 300 m 2 /g above the STSA.
- the true density of the biogenic black pigment is preferably less than 1.6 g/cm 3 , particularly preferably less than 1.5 g/cm 3 .
- the true density is determined by means of helium pycnometry, for example in a helium pycnometer (Pycnomatic ATC) from Porotec GmbH at a temperature of 20°C.
- the particle size distribution of the biogenic black pigment is determined according to DIN ISO 13320:2020.
- the samples are prepared by dispersing the biogenic black pigment for 10 minutes with an Ultraturax at approx. 1% by mass in distilled water.
- the sample preparation can be supplemented by the use of ultrasound with a defined energy input of preferably 6,000 Ws or 12,000 Ws. Ultrasonic treatment leads to deagglomeration. Irrespective of whether the sample preparation takes place with or without ultrasonic treatment, the particle size distribution is measured using ultrasound.
- the D99 value of the Q3 cumulative curve distribution of the grain size distribution without sample preparation with ultrasound of the biogenic black pigment is less than 100 pm. It is preferably less than 50 ⁇ m, particularly preferably less than 20 ⁇ m, particularly preferably less than 15 ⁇ m, in particular less than 10 ⁇ m, in some embodiments less than 5 ⁇ m. It is preferably more than 0.5 ⁇ m, preferably more than 1 ⁇ m, in particular more than 2 ⁇ m. As mentioned above, the D99 value is determined according to DIN ISO 13320:2020.
- the biogenic black pigment according to the invention preferably has a D50 value of the Q3 cumulative curve distribution of the grain size distribution of 10 nm to 5000 nm. It is preferably more than 100 nm, moreover preferably more than 200 nm, particularly preferably more than 500 nm, in particular at more than 750 nm.
- the D50 value of the Q3 cumulative curve distribution of the grain size distribution is preferably less than 4000 nm, more preferably less than 3000 nm, in particular less than 2000 nm, furthermore preferably less than 1000 nm. As mentioned above, the D50 value is determined according to DIN ISO 13320:2020.
- the D99 (or the D50) of the Q3 cumulative curve distribution is the D99 (or the D50) of the Q3 cumulative curve distribution.
- Grain size distribution which was measured after sample preparation by ultrasonic treatment with 6000 Ws energy input at a maximum of 70%, more preferably at a maximum of 60% of the D99 (or the D50) of the Q3 cumulative curve distribution of the grain size distribution, which was measured after sample preparation without ultrasonic treatment.
- the D99 (or the D50) of the Q3 cumulative curve distribution is the D99 (or the D50) of the Q3 cumulative curve distribution.
- Grain size distribution which was measured after sample preparation by ultrasonic treatment with 6000 Ws energy input, at least 10%, more preferably at least 20% of the D99 (or the D50) of the Q3 cumulative curve distribution of the grain size distribution was measured after sample preparation without ultrasonic treatment.
- the black pigment according to the invention is preferably used in a concentration of at least 1% and at most 5%, preferably at most 4%, more preferably at most 3%.
- An exemplary biogenic black pigment according to the invention is characterized by the following colorimetric values, preferably when using 1 or 2%, particularly preferably 1%, in PVC-p or polypropylene, preferably polypropylene:
- Color data (also referred to herein as colorimetric values) such as L*(D65), a*(D65), b*(D65), dL*(D65), da*(65), db*(D65) and dE*ab(D65 ) are collected in the sense of the present invention in particular by means of a spectrophotometer with CIE standard illumination D65.
- the diffuse geometry also spherical geometry, diffuse/8°, d/8°
- specularity SPIN [specular included] or RSIN [reflectance specular included]
- the biogenic black pigment of the invention preferably has an L*(D65) value of greater than 23, preferably greater than 24 and less than 26, preferably less than 25.
- the biogenic black pigment of the invention preferably has an a*(D65) value of greater than -0.4, preferably greater than -0.2, particularly preferably greater than -0.1 and less than 0.2.
- the biogenic black pigment of the invention preferably has a b*(D65) value of greater than -0.5, preferably greater than -0.2, particularly preferably greater than -0.1 and less than 0.2.
- the biogenic black pigment according to the invention preferably has a dL*(D65) value of greater than 1.3 and less than 1.4.
- the biogenic black pigment of the invention preferably has a da*(D65) value of greater than 0.03 and less than 1.0.
- the biogenic black pigment of the invention preferably has a db*(D65) value of greater than -0.7 and less than -0.5.
- the biogenic black pigment of the invention preferably has a dE*ab(D 65) value of greater than 1.2 and less than 1.5.
- the values preferably relate in each case to use of the black pigment in PVC-p or polypropylene, preferably polypropylene, preferably in an amount of 1 or 2%, particularly preferably 1%.
- % preferably means % by mass.
- the black pigment is particularly preferably characterized by the following colorimetric values, preferably when using 2% in PVC-p;
- colorimetric values compare favorably with the colorimetric values of customary and known, commercially available carbon black pigments.
- a suitable reference pigment is e.g. Printex 30 from Orion Engineered Carbon.
- the biogenic black pigment according to the invention is preferably produced using the method according to the invention.
- At least one biogenic, particulate carbon material is used
- the biogenic, particulate carbon material used is preferably not itself a black pigment, in particular not black.
- the BET surface area of the biogenic, particulate carbon material preferably deviates from its STSA surface area by a maximum of 20%.
- a 15 percent suspension of the biogenic, particulate carbon material in distilled water preferably has an electrical conductivity of ⁇ 5 mS/cm.
- the biogenic, particulate carbon material preferably has a D/G ratio of 0.2 to 9.0 as a measure of the proportion of graphitic carbon in the Raman spectrum.
- the biogenic, particulate carbon material preferably has a D90 value of the Q3 particle size distribution of ⁇ 30 ⁇ m.
- Lignin-containing biomass in particular lignin-containing biomass with a proportion of Klason lignin greater than 80% by mass, based on the dry matter, is preferably used to produce the biogenic, particulate carbon material (cf. DE 10 2016 201 801 A1, paragraph [0040]; Science Direct: Klason Lignin - an overview
- biomass any biomass is referred to as biomass here, the term “biomass” herein so-called phytomass, i.e. biomass originating from plants, zoomass, i.e. biomass originating from animals, and microbial biomass, i.e. biomass originating from microorganisms including fungi, encompasses it the biomass is dry biomass or fresh biomass and originates from dead or living organisms.
- the most preferred biomass used herein to prepare the black pigment is phytomass, preferably dead phytomass.
- Dead phytomass includes, but is not limited to, dead, shed, or severed plants and components.
- the starting product described above (biogenic, particulate carbon material) is preferably pyrolyzed at a temperature of Tp yroiyse from 250° C. to 600° C., preferably from 350° C. to 500° C. It is advantageous to keep T pyrolysis between 1 minute and 180 minutes.
- Tp yroiyse from 250° C. to 600° C.
- the oxygen content of the atmosphere is preferably more than 0.5% by volume.
- the pyrolysis is carried out in a drum furnace, a fluidized bed dryer, a fluidized bed reactor or a rotary kiln.
- the pyrolysis is preferably carried out in a fluidized bed, in a rotary kiln or in a rotary kiln under an inert gas.
- the protective gas preferably consists of nitrogen and/or carbon dioxide or of nitrogen and/or carbon dioxide with an oxygen content of ⁇ 10% by volume, preferably less than 5% by volume, particularly preferably less than 2.5% by volume, more preferably less than 2 Vol%.
- the oxygen content of the protective gas is preferably more than 0.5% by volume.
- the protective gas in the rotary kiln is fed in countercurrent to the product flow.
- the starting material biogenic, particulate carbon material
- the resulting biogenic black pigment is preferably subjected to fine grinding.
- the fine grinding is carried out in such a way that the particle size of the biogenic black pigment is adjusted to the above-mentioned ranges of the D99 value and the D50 value of the Q3 cumulative curve distribution.
- the preferred dry grinding process is gas jet grinding, preferably in a classifier mill using air, nitrogen or superheated steam as the grinding gas.
- Another preferred grinding method is grinding with grinding bodies in an annular mill.
- the preferred wet grinding process is wet grinding, for example using grinding media in an agitator ball mill.
- Glass beads or ceramic beads which preferably have a diameter of 2 mm to 10 mm, are preferably used as grinding media.
- the suspension of the biogenic black pigment according to the invention resulting from the wet grinding preferably has a pH of between 5 and 11.
- Formic acid can be added to the suspension until a pH of less than 7 is reached. Treatment with formic acid can also further reduce the heavy metal content.
- the biogenic black pigment according to the invention is filtered and the filter cake is washed with water until the conductivity of the filtrate is ⁇ 300 pS/cm.
- the filter cake is preferably dried at ⁇ 80° C., and the dried biogenic black pigment is then preferably deagglomerated in a mill.
- the suspension of the biogenic black pigment according to the invention is dried in a spray dryer.
- biogenic black pigment according to the invention is outstandingly suitable for the achromatic coloring and tinting of plastics, plastic parts, coating materials, printing inks, inks, paints, paper, cardboard and mineral materials, and as reinforcing fillers for rubber-like, thermoplastic, liquid-crystalline and magnetorheological elastomers.
- the materials and objects according to the invention in particular the plastics, plastic granules, plastic moldings, coating materials and coatings, printing inks and prints, inks and images and documents produced with these inks, paints and coatings, paper, cardboard, cartons, mineral materials and components and components from Rubber-like, thermoplastic, liquid-crystalline and magnetorheological elastomers, all of which contain at least one biogenic black pigment according to the invention, have particularly advantageous application properties such as excellent color strength, color strength, color fastness, color stability, light fastness and light stability, and in their function as reinforcing fillers, even in low proportions by mass, an excellent reinforcing effect Effect on.
- thermogenic black pigment according to the invention with a concentration of at least 1% and at most 5%, preferably at most 4%, more preferably at most 3%, and the following colorimetric values have:
- Preferred materials which contain the biogenic black pigment according to the invention comprise or consist of a matrix material selected from the following list: polyester, polyethylene, polypropylene, polyester carbonates, polyamides, polyimides, polyester amides, polyetherimides, polyurethanes, polyvinyl alcohols, polyvinyl acetates, polyvinyl chlorides, polymetacrylates, 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-formaldehyde resin, melamine-phenol resins, phenol-formaldehyde resins; Silicone polymer, natural rubber, styrene butad
- the preferred use of the materials containing the biogenic black pigment according to the invention is the production of children's toys, car interior trim, plastic granules for extrusion processes or food packaging.
- a clamping building block which contains the biogenic black pigment according to the invention with a concentration of at least 1% and at most 5%, preferably at most 4%, more preferably at most 3%, having at least 4 elevations and at least one depression, with at least one depression being designed in this way that it can accommodate at least one elevation of another clamping block, thereby creating a clamping connection between two clamping blocks, and which has the following colorimetric values:
- the invention is substantiated by the following examples.
- the examples are not limitative but exemplify the nature and purpose of the invention.
- the person skilled in the art can readily provide further examples on the basis of the technical teaching without being inventive himself.
- the brown, finely divided, biogenic, particulate carbon materials are produced from kraft lignin using the following process steps:
- the starting products were pyrolyzed in a laboratory rotary kiln from NaberTherm with an inner glass tube having a length of 73 cm and a diameter of 10 cm.
- the pyrolysis conditions can be found in Table 2.
- the PAH content was particularly low.
- the black pigment PD-4 was treated with BYK® 90761 as a finish, incorporated into polypropylene (Daplen® 3007) and subjected to a comparative colorimetric measurement.
- the black pigments Printex® 30 and LampBlack (Color Index Pigment Black 6 (77266); grain size 90 to 120 nm) served as comparison pigments.
- a further comparison was carried out in relation to the starting material ES-B used.
- the results of the colorimetric Measurements can be found in Table 4. In each case 1 wt
- the biogenic black pigment PD-4 according to the invention could very easily be incorporated homogeneously into the polypropylene.
- the colored polypropylene had excellent colorimetric values, which in particular are much better than the values determined for the starting material ES-B.
- a porcelain crucible with a volume of 100 ml was filled to the brim with 15.38 g of the brown, finely divided, particulate, biogenic carbon material ES-A and packed airtight with aluminum foil.
- the crucible was then tempered in a muffle furnace at 500°C for 30 minutes; after this time the development of smoke gas had ended. After cooling, the crucible was unpacked.
- the yield of the biogenic black pigment according to the invention was 9.54 g, which corresponds to a yield after carbonization of 62.03%.
- the black pigment was ground for 48 hours in a 1.5 L ball mill with 180 g of water, 4.5 g of BYK® 9076 and 500 g of 10 mm diameter porcelain balls.
- the pigment suspension was then separated from the porcelain balls using a sieve, filtered off in a Büchner funnel with a vacuum using special filter paper (from Macherey-Nagel, MN 85/70), dried in a drying cabinet at 60 °C and then placed in ground in an impact mill for 4 minutes.
- Example 6 The performance properties of the biogenic black pigment of Example 5 according to the invention were outstanding.
- Example 6 The performance properties of the biogenic black pigment of Example 5 according to the invention were outstanding.
- the black pigment of Example 6 was ground in screw-top jars with a volume of 250 ml, an internal diameter of 62 mm and an internal height of 75 mm. In each case, 150 g of glass beads with a diameter of 2.8 to 3.4 mm, 90 ml of water and 10.0 g of black pigment 7 were introduced into a screw-top jar. 0.5 g Byk® 9076 was added as an additive. Four of these filled screw-top jars were placed in a holder and ground twice for 10 minutes each in a paint dispenser from Olbrich Know-How.
- the pigment suspension 8 was then separated from the glass beads using a sieve, filtered off in a Büchner funnel with a vacuum through a special filter paper (from Macherey-Nagel, MN 85/70), dried at 60° C. in a drying cabinet and then in a Impact mill ground for 4 minutes.
- the resulting biogenic black pigment 7 according to the invention also had outstanding performance properties. example 8
- the black pigment of Example 6 was ground in screw-top jars with a volume of 250 ml, an internal diameter of 62 mm and an internal height of 75 mm.
- 150 g of glass beads with a diameter of 2.8 to 3.4 mm, 90 ml of water and 10.0 g of black pigment 7 were introduced into a screw-top jar.
- 0.5 g Geniosil GF 96 was added as an additive.
- Four of these filled screw-top jars were placed in a holder and ground twice for 10 minutes each in a paint dispenser from Olbrich Know-How.
- the pigment suspension 9 was then separated from the glass spheres using a sieve, and the glass spheres were cleaned of black pigment 9 still adhering with water.
- the pH of the pigment suspension 9 was 9.4.
- the pigment suspension 9 was then filtered off in a Buchner funnel under reduced pressure through special filter paper (from Macherey-Nagel, MN 85/70), dried in a drying cabinet at 80° C. and ground in a hammer mill for 4 minutes.
- This biogenic black pigment 8 according to the invention also had outstanding performance properties.
- the black pigment of Example 6 was ground in screw-top jars with a volume of 250 ml, an internal diameter of 62 mm and an internal height of 75 mm.
- 150 g of glass beads with a diameter of 2.8 to 3.4 mm, 90 ml of water and 10.0 g of black pigment 7 were placed in a screw-top jar.
- 0.5 g Geniosil GF 96 was added as an additive.
- Four of these filled screw-top jars were placed in a holder and ground twice for 10 minutes each in a paint dispenser from Olbrich Know-How.
- the pigment suspension was then separated from the glass beads using a sieve; the glass beads were cleaned with water to remove any black pigment 9 still adhering.
- the pH of the pigment suspension was 9.9.
- a fraction of pigment suspension 9 was further processed in example 10.
- the remaining fraction was further processed as follows:
- the pigment suspension was then filtered off in a Buchner funnel under reduced pressure through special filter paper (from Macherey-Nagel, MN 85/70), dried in a drying cabinet at 80° C. and ground in a hammer mill for 4 minutes.
- the analytically determined heavy metal contents are listed in Table 5. The analysis was carried out according to DIN EN ISO 11885, 2009-09 edition.
- Example 10 The production of the biogenic black pigment 10 according to the invention
- the pigment suspension from example 9 was first adjusted to a pH of ⁇ 6 with formic acid.
- the resulting pigment suspension was then filtered off in a Buchner funnel under reduced pressure through a special filter paper (from Macherey-Nagel, MN 85/70).
- the pigment filter cake was washed to reduce the conductivity and thus the salt content of the black pigment 10 to a conductivity of ⁇ 300 pS/cm of the wash water.
- the black pigment 10 obtained was dried at 80° C. in a drying cabinet and ground in an impact mill for 4 minutes.
- the analytically determined heavy metal contents are listed in Table 5. The analysis was carried out according to DIN EN ISO 11885, 2009-09 edition.
- Table 5 Determination of the heavy metal content of black pigments 9 and 10 according to DIN EN ISO 11885, 2009-09 edition in mg/kg (ppm) By treating the black pigment 9 with formic acid according to Example 10, a significant reduction in the heavy metal content was achieved.
- pigments are their colorimetric properties such as hue and color strength. These properties can only be determined in colorations in polymeric materials in comparison to a reference pigment.
- the black pigments of Examples 1 to 10 according to the invention were tested in PVC-p, produced analogously to DIN EN 14469-1 and DIN EN 14469-2, or in polyethylene.
- biogenic black pigments of Examples 1 to 10 according to the invention exhibited excellent shades and color strengths in comparison with conventional black pigments.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
- Carbon And Carbon Compounds (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
Claims
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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EP21172354 | 2021-05-05 | ||
PCT/EP2022/062166 WO2022234023A1 (de) | 2021-05-05 | 2022-05-05 | Biogenes schwarzpigment, verfahren zu seiner herstellung und seine verwendung |
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EP4334396A1 true EP4334396A1 (de) | 2024-03-13 |
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EP22727864.5A Pending EP4334396A1 (de) | 2021-05-05 | 2022-05-05 | Biogenes schwarzpigment, verfahren zu seiner herstellung und seine verwendung |
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EP (1) | EP4334396A1 (de) |
JP (1) | JP2024518930A (de) |
KR (1) | KR20240004962A (de) |
WO (1) | WO2022234023A1 (de) |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
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DE2846405A1 (de) | 1978-10-25 | 1980-05-08 | Degussa | Pigmentruss fuer schwarzlacke |
US4393034A (en) | 1980-10-22 | 1983-07-12 | Ashland Oil, Inc. | Energy efficient process for the production of carbon black |
IN168779B (de) | 1986-03-24 | 1991-06-01 | Cabot Corp | |
DE102016201801A1 (de) * | 2015-11-21 | 2017-05-24 | Suncoal Industries Gmbh | Partikelförmiges Kohlenstoffmaterial herstellbar aus nachwachsenden Rohstoffen und Verfahren zu dessen Herstellung |
-
2022
- 2022-05-05 JP JP2023568088A patent/JP2024518930A/ja active Pending
- 2022-05-05 KR KR1020237041853A patent/KR20240004962A/ko unknown
- 2022-05-05 WO PCT/EP2022/062166 patent/WO2022234023A1/de active Application Filing
- 2022-05-05 EP EP22727864.5A patent/EP4334396A1/de active Pending
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JP2024518930A (ja) | 2024-05-08 |
KR20240004962A (ko) | 2024-01-11 |
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