WO2023074225A1 - Charge carbonée support de noir de carbone - Google Patents

Charge carbonée support de noir de carbone Download PDF

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Publication number
WO2023074225A1
WO2023074225A1 PCT/JP2022/035845 JP2022035845W WO2023074225A1 WO 2023074225 A1 WO2023074225 A1 WO 2023074225A1 JP 2022035845 W JP2022035845 W JP 2022035845W WO 2023074225 A1 WO2023074225 A1 WO 2023074225A1
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WO
WIPO (PCT)
Prior art keywords
carbon black
carbonaceous
carbonaceous material
supporting
carbon
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Application number
PCT/JP2022/035845
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English (en)
Japanese (ja)
Inventor
孝陽 金井
洋之 内野
Original Assignee
三洋貿易株式会社
日本微粒子材料株式会社
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Application filed by 三洋貿易株式会社, 日本微粒子材料株式会社 filed Critical 三洋貿易株式会社
Publication of WO2023074225A1 publication Critical patent/WO2023074225A1/fr

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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
    • 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
    • C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
    • 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
    • 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
    • C09D17/00—Pigment pastes, e.g. for mixing in paints

Definitions

  • the present invention relates to a carbon black-supported carbon that can be easily dispersed in a resin precursor, which is a raw material of a resin, without impairing the properties such as electrical properties and colorability possessed by the carbonaceous filler and without using a dispersant.
  • a resin precursor which is a raw material of a resin
  • it relates to a carbon-carrying carbon that can be easily dispersed in polyols as raw materials for polyurethane.
  • Polyols in the present invention are polyhydric alcohols that serve as raw materials or intermediates for resins, and raw materials or intermediates for phenol resins, urea resins, melamine resins, modified unsaturated polyester resins, alkyd resins, and epoxy resins in addition to polyurethanes.
  • Polyurethane is a reaction product of polyols and polyisocyanates.It has excellent moldability, various forms, and a wide range of mechanical properties.It is used for gravure ink, synthetic leather, elastomers, paints, adhesives, and coatings. It is widely used as a cushioning material.
  • polyurethane has disadvantages such as being easily decomposed by light, heat, etc., and being easily charged.
  • a method of blending a carbonaceous filler is implemented in various applications.
  • phenolic resins, urea resins, melamine resins, modified unsaturated polyester resins, raw materials for alkyd resins, and epoxy resins for the same purpose as for polyurethanes, a technique of blending carbonaceous fillers is implemented in various applications.
  • carbon black may have insufficient dispersibility in resin precursors and resins. For example, even if a large amount of carbon black, which is a typical carbonaceous filler, is added to polyurethane, the dispersibility of carbon black and polyols is poor. This is because the carbon black surface has few functional groups that increase affinity with polyols, and the affinity with polyols is not good. This is because the carbon blacks aggregate with each other.
  • the present inventors have found that the carbonaceous filler exhibits good dispersibility in the resin precursor without chemically changing the surface or using a dispersant or the like, which may impair the original properties of the carbonaceous filler.
  • carbonaceous particles having a specific average particle diameter and containing many phenolic hydroxyl groups as surface functional groups were used as the carbonaceous material.
  • the present inventors have found that a carbon black-supporting carbonaceous filler having carbon black supported on its surface achieves the object, and completed the present invention.
  • the present invention provides a carbon black-supporting carbonaceous filler in which carbon black is supported on a carbonaceous material.
  • the carbonaceous material may have a component content (dry basis weight) of 80% or more fixed carbon content, less than 8% volatile content, and less than 4% ash content as defined in JIS-M 8812:2004.
  • the carbonaceous material may have 0.005 mmol/m 2 or more of phenolic hydroxy groups per external specific surface area.
  • the carbonaceous material may be carbonaceous particles having an average particle diameter (D50) of 0.1 to 100 ⁇ m.
  • the carbon black-supporting carbonaceous filler may support 1 part by weight or more and 200 parts by weight or less of carbon black with respect to 100 parts by weight of the carbonaceous material.
  • the carbon black may have an average particle size of 0.01 to 0.3 ⁇ m.
  • the true specific gravity of the carbonaceous material may be 1.5 or less.
  • the carbonaceous material may be a carbonaceous material selected from bio-carbons.
  • the carbonaceous material may be a bio-raw material mainly composed of lignin/cellulose/hemicellulose or a carbonaceous material obtained by carbonizing low-carbonized lignite at 1000° C. or lower.
  • the carbon black-supporting carbonaceous filler may be used for dispersing and blending in polyols, which are raw materials for thermosetting resins such as polyurethane.
  • the carbon black-supporting carbonaceous filler is a carbonaceous material that firmly supports carbon black and contains many phenolic hydroxy groups in the functional groups on the surface. It exhibits good dispersibility against other thermosetting resins such as polyurethane, and a large amount of carbon black component can be easily blended into thermosetting resins such as polyurethane without using a dispersant.
  • Various properties expected of carbonaceous fillers such as prevention properties, coloring properties, and electrical conductivity, can be exhibited more strongly.
  • the carbonaceous material used in the present invention has a six-membered carbon ring structure as its chemical structure, and the hydroxy group (OH), which has a high affinity for polyols, is directly bonded to the six-membered carbon ring. is valid. This is completely different from the technology in which the carboxyl group (COOH) is effective as a surface property for dispersing in water.
  • the external surface area herein In the book, the abundance (mmol/m 2 ) of phenolic hydroxy groups (Ph-type OH) per surface area is referred to as “external specific surface area”.
  • the amount of functional groups per external specific surface area is an index indicating the amount of functional groups on the surface of the carbonaceous material.
  • This index is calculated from the measurement of the total amount of acidic functional groups and the amount of strongly acidic functional groups using the acid-base titration Boehm method, and the measurement of the external specific surface area STSA.
  • it is the phenolic hydroxyl group, not the alkyl hydroxyl group, that is sought by the Boehm method. That is, it is a value obtained by taking the amount of strongly acidic functional groups as the amount of carboxyl groups (COOH), taking the difference between the amount of all acidic functional groups and the amount of strongly acidic functional groups as the amount of phenolic hydroxy groups, and dividing it by the external specific surface area STSA.
  • the amount of phenolic hydroxy groups (Ph OH) should be 0.005 mmol/m 2 or more per external specific surface area, and the amount of carboxyl groups (COOH) should be 0.001 mmol/m 2 or less per external specific surface area. It is desirable to have The amount of phenolic hydroxy groups per external specific surface area is preferably 0.010 mmol/m 2 or more. Although the upper limit is not particularly limited, it is expected that production will be difficult if it exceeds about 0.10 mmol/m 2 in terms of mass production.
  • the external specific surface area (STSA) of the carbonaceous material may be 0.01-100 m 2 /g, preferably 0.1-10 m 2 /g. More desirably, it may be 0.3 to 5 m 2 /g.
  • the carbonaceous material has an average particle diameter (D50) of 0.1 ⁇ m or more and 100 ⁇ m or less, preferably 1 ⁇ m or more.
  • the carbonaceous particles are 20 ⁇ m or less. If the average particle size (D50) is smaller than this, the carrier carbon tends to aggregate with each other, making it difficult to support carbon black. If it is larger than this, uniformity will be lost.
  • the average particle size (D50) may be measured, for example, with a CPS Instruments disc centrifugal particle size distribution analyzer, Model DC24000UHR.
  • the carbonaceous material should have a fixed carbon content of 80% or more and a volatile content of less than 8% as defined in JIS-M 8812: 2004 as a dry basis weight. desirable.
  • the ash content is desirably less than 4% because it does not contribute to performance as a filler.
  • a material with a volatile content of 8% or more cannot be applied because the six-membered carbon ring is underdeveloped and there are many hydrocarbon (CH) moieties that do not exhibit properties as a carbonaceous filler. It is preferably 85% or more fixed carbon, more preferably 90% or more fixed carbon.
  • the true specific gravity is closer to the specific gravity (about 1.00 to 1.30) of the resin precursor such as polyols, the better the long-term dispersion stability. 50 or less is desirable.
  • Biocarbon is a carbonaceous material obtained by carbonizing organic matter (biomass) such as agricultural and forestry waste, waste wood, and food waste. Examples thereof include biomaterials mainly composed of lignin, cellulose, and hemicellulose, or carbonaceous materials obtained by carbonizing low-carbonized lignite coal (such as Australian lignite) at 1000°C or lower, preferably 800°C or lower.
  • a carbonaceous material may also be obtained by introducing a phenolic hydroxy group into a relatively high-purity carbon material such as coal, graphite, or graphene.
  • methods for introducing phenolic hydroxy groups include oxygen plasma irradiation, UV and/or ozone oxidation treatment, ion beam irradiation, gas phase oxidation using gas, and liquid phase oxidation using acid, hydrogen peroxide, or the like. Law, etc. may be used.
  • oxygen plasma irradiation UV and/or ozone oxidation treatment
  • ion beam irradiation gas phase oxidation using gas
  • liquid phase oxidation using acid, hydrogen peroxide, or the like. Law, etc. may be used.
  • the method of low-temperature carbonization of bio-raw materials or low-carbonized lignite coal which are organic substances already having oxygen-containing groups, relatively easily controls the formation of functional groups to produce the carbonaceous material of the present invention. It is usually preferred because it gives you material.
  • the carbon black supported on the carbonaceous material is not particularly limited, and any of furnace black, thermal black, channel black, etc. can be used.
  • the carbonaceous material can impart basic physical properties as a carbonaceous filler, such as weather resistance, antistatic properties, reinforcing properties, and coloring properties, and can also impart various properties of each carbon black, such as electrical conductivity.
  • Carbon black having an average particle diameter (arithmetic mean diameter by microscopic observation) of preferably 0.01 to 0.3 ⁇ m (10 to 300 nm) is used. In the measurement using an electron microscope, the diameter may be measured by irradiating a circular spotlight capable of changing the circular diameter onto the peripheral portion of the particle in the image measured by the electron microscope.
  • the ratio of carbon black supported on the carbonaceous material is preferably 1% by weight or more and 200% by weight or less, more preferably 1% by weight or more and 100% by weight or less, still more preferably 1% by weight, with respect to 100 parts by weight of the carbonaceous material. part or more and 50 parts by weight or less. If the content of carbon black is less than this, the effect of adding carbon black will be insufficient. On the other hand, if it exceeds this range, it becomes difficult to carry, and there is a concern that unsupported carbon black may cause poor dispersion.
  • the carbon black is supported by mechanically contacting the carbonaceous material as a carrier with the carbon black.
  • carbon-based particles in which six-membered carbon rings are developed are brought into contact with each other, strong irreversible bonds are formed between the particles.
  • it can be carried out by mechanically applying strong pressure to the particles using an automatic mortar, ball mill, crusher, or the like.
  • Whether or not carbon black is supported on the carbonaceous filler can be easily visually confirmed by, for example, whether or not the carbon black precipitates or aggregates in the polyol liquid when the carbonaceous filler is dispersed in the polyol liquid. can.
  • the carbon black-supporting carbonaceous filler of the present invention is suitably dispersed in a resin precursor which is a raw material of the resin.
  • carbon black-supporting carbonaceous fillers can be suitably dispersed and blended in polyols, which are raw materials for thermosetting resins such as polyurethane.
  • the polyols are those generally used as raw materials for polyurethane and other thermosetting resins, and are not particularly limited. . Modified or mixed products thereof, or prepolymers obtained by partially polymerizing them may be used.
  • Polyols include phenolic resins, their modified products and their intermediates, intermediates of urea resins and melamine resins, intermediates of modified unsaturated polyester resins, bisphenol A prepolymers and urethane prepolymers which are raw materials for alkyd resins and epoxy resins. may be When a large amount of carbon black-supporting carbonaceous filler is mixed, it is preferable to select one having a viscosity that takes workability into consideration.
  • the carbon black-supporting carbonaceous filler of the present invention When the carbon black-supporting carbonaceous filler of the present invention is blended with polyols, it can be mixed at any ratio, but in practice, the content of the carbon black-supporting carbonaceous filler is preferably 1 to 80% by weight. range, more preferably 5-70% by weight. If it is less than this, for example, when it is mixed with polyols and isocyanates, which are polyurethane raw materials, it will be diluted, and the characteristics of the carbon black-supporting carbonaceous filler will be difficult to develop. On the other hand, if this is exceeded, uniform mixing becomes difficult and not practical. Phenol resins, urea resins, melamine resins, modified unsaturated polyester resins, alkyd resins and epoxy resins are also diluted by mixing with other raw materials. It is preferably blended in the range of 5 to 70% by weight.
  • the dispersion obtained by dispersing and blending the carbon black-supporting carbonaceous filler of the present invention in polyols is used as polyols for resin raw materials such as polyurethane as it is, raw materials such as polyisocyanates in a predetermined amount, and auxiliary raw materials as necessary.
  • resin raw materials such as polyurethane as it is, raw materials such as polyisocyanates in a predetermined amount, and auxiliary raw materials as necessary.
  • it can be mixed with a catalyst, a foam stabilizer, a foaming agent, a cross-linking agent, etc. and cured to obtain a resin product such as polyurethane having a high carbon black content.
  • flame retardants, fillers, colorants, stabilizers, release agents, and the like may be added depending on the purpose and application.
  • Solvents may be used for dilution and the like.
  • a dispersion obtained by dispersing and blending the carbon black-supporting carbonaceous filler of the present invention with polyols is used as a masterbatch, and this masterbatch dispersion is mixed with raw materials such as polyols, and these are blended with polyisocyanates. It can also be cured later to obtain a resin product such as a polyurethane product with the desired carbonaceous filler content.
  • Resin products such as polyurethane obtained in this way have a high carbonaceous filler content due to the fine and uniform dispersion of the carbonaceous filler. Since the properties can be fully expressed, it can be suitably used in various applications such as inks, synthetic leathers, elastomers, paints, adhesives, coatings, and cushioning materials.
  • Carbonaceous material CC1 Pulverized charcoal product derived from pine wood carbonized at 550°C (manufactured by CarbonNeat, Sanyo Trading Sales “Neat90”) Average particle size (D50) 5 ⁇ m External specific surface area (STSA) 1 m 2 /g True specific gravity 1.12 Industrial analysis 96.1% fixed carbon, 1.8% volatiles, 2.1% ash (dry basis weight) Ph-type OH group amount per external specific surface area: 0.080 mmol/m 2 Amount of COOH groups per external specific surface area: Below measurement limit External specific surface area (STSA) 0.5 m 2 /g True specific gravity 1.1 Industrial analysis 90.3% fixed carbon, 2.5% volatiles, 7.2% ash (dry basis weight) Ph OH group amount per external specific surface area 0.005mmol/m 2 COOH group amount per external specific surface area: below measurement limit
  • Carbon black CB1 “N220” grade equivalent, average particle size 0.02 ⁇ m (20 nm) True specific gravity 1.8-1.9 Volatile content 1.0%, ash content 0.03% Nitrogen adsorption specific surface area (N2SA) 120m 2 /g External specific surface area (STSA) 106m 2 /g DBP absorption 114mL/100g Ph-type OH group amount per external specific surface area: 0.00085 mmol/m 2 COOH group amount per external specific surface area: 0.00028 mmol/m 2 Carbon black CB2: "N990" grade equivalent, average particle size 0.3 ⁇ m (300 nm) True specific gravity 1.9 Volatile content 0.5%, ash content 0.1% Nitrogen adsorption specific surface area (N2SA) 8m 2 /g External specific surface area (STSA) 8m 2 /g DBP absorption 40mL/100g Ph-type OH group amount per external specific surface area: 0.00025 mmol/m 2 COOH
  • Examples 1 to 10 Reference Examples, Comparative Examples 1 and 2
  • the obtained carbon black-supporting carbonaceous fillers A1 to A10, and carbon blacks CB1 and CB2 for comparison were used and blended with polyols to confirm their dispersibility.
  • polyurethanes were produced by blending with polyisocyanates.
  • the following materials were used as polyols and polyisocyanates.
  • Polyol B1 Polyether polyol "P-3000" manufactured by ADECA
  • Polyol B2 urethane foam resin for casting manufactured by Nisshin Resin Co., Ltd.
  • Liquid A polyol polyisocyanate C1 urethane foam resin for casting B liquid diisocyanate manufactured by Nisshin Resin Co., Ltd.
  • Table 1 also shows the state of dispersion of the carbon black-supported carbon and the physical properties of the obtained polyurethane resin.
  • the dispersibility of the carbon black-supporting carbonaceous filler in polyols was evaluated according to the following criteria. A: Fluid and well dispersed. O: Viscosity increased and no fluidity, but dispersed. x: A gel-like undispersed mass is generated or separated and precipitated from polyols, and cannot be dispersed. In any of Examples 1 to 10, when the carbonaceous filler was dispersed in the polyol liquid, carbon black did not precipitate or aggregate in the polyol liquid, and carbon black was supported on the carbonaceous material. It could be confirmed.
  • the specific volume resistivity ( ⁇ cm) of the polyurethanes obtained in Examples 8 and 10 was simply measured by a two-electrode method and found to be 2.4 ⁇ 10 4 ⁇ cm and 4.5 ⁇ 10 6 ⁇ cm, respectively. It was confirmed that the black-supporting carbonaceous filler also exhibits electrical conductivity, which is a characteristic of carbon black. In Comparative Examples 1 and 2, carbon black could not be dispersed in polyols, and polyurethane molded articles could not be obtained.
  • the polyurethanes produced in Examples 4 to 10 and Reference Example were molded, and their appearance was evaluated according to the following criteria. ⁇ : Aggregation derived from carbon black or the like was not confirmed at all, and the appearance was good. ⁇ : Aggregation was confirmed slightly, but there was no problem in practical use and appearance. x: Aggregation of carbon black or the like occurred.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Pigments, Carbon Blacks, Or Wood Stains (AREA)

Abstract

L'invention concerne une charge carbonée support de noir de carbone telle qu'un noir de carbone est supporté par un matériau carboné. Ce matériau carboné présente une teneur (poids de base sèche) de 80% ou plus en carbone fixe, de moins de 8% en composant volatile et de moins de 4% en taux de cendres selon une analyse immédiate. Cette charge carbonée support de noir de carbone est caractéristique en ce qu'un groupe hydroxy phénolique représente ０,００５ｍmole/ｍ２ ou plus par surface spécifique de partie externe, en ce qu'elle consiste en des particules carbonées de diamètre particulaire moyen （D50） compris entre ０,１ et １００μｍ, et en ce que le noir de carbone est supporté à raison d'une plage de 1 partie en masse ou plus à 200 parties en masse ou moins pour 100 parties en masse de matériau carboné.
PCT/JP2022/035845 2021-10-29 2022-09-27 Charge carbonée support de noir de carbone WO2023074225A1 (fr)

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JP2021-177080 2021-10-29
JP2021177080 2021-10-29

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Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0137407B2 (fr) * 1981-01-21 1989-08-07 Idemitsu Kosan Co
JP2015196744A (ja) * 2014-03-31 2015-11-09 大王製紙株式会社 顔料分散液用の炭素微粒子の製造方法、顔料分散液の製造方法、顔料分散液用の炭素微粒子、顔料分散液、及びインクジェット用インク
CN108793119A (zh) * 2017-05-03 2018-11-13 申广 一种炭黑和石墨烯微片复合材料制备技术
JP2019503954A (ja) * 2015-11-21 2019-02-14 サンコール インダストリーズ ゲゼルシャフト ミット ベシュレンクテル ハフツングＳｕｎｃｏａｌ Ｉｎｄｕｓｔｒｉｅｓ Ｇｍｂｈ 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
WO2020220047A1 (fr) * 2019-04-26 2020-10-29 Thomas Jefferson University Encre durable à base de biocharbon présentant des propriétés conductrices
KR20210038376A (ko) * 2019-09-30 2021-04-07 주식회사 엘지화학 스티렌-공액디엔계 중합체 고무 조성물
KR20210092392A (ko) * 2020-01-16 2021-07-26 경상국립대학교산학협력단 리그닌 유래 활성탄의 제조방법 및 이에 따라 제조된 활성탄을 포함하는 고분자 복합재료

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0137407B2 (fr) * 1981-01-21 1989-08-07 Idemitsu Kosan Co
JP2015196744A (ja) * 2014-03-31 2015-11-09 大王製紙株式会社 顔料分散液用の炭素微粒子の製造方法、顔料分散液の製造方法、顔料分散液用の炭素微粒子、顔料分散液、及びインクジェット用インク
JP2019503954A (ja) * 2015-11-21 2019-02-14 サンコール インダストリーズ ゲゼルシャフト ミット ベシュレンクテル ハフツングＳｕｎｃｏａｌ Ｉｎｄｕｓｔｒｉｅｓ Ｇｍｂｈ 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
CN108793119A (zh) * 2017-05-03 2018-11-13 申广 一种炭黑和石墨烯微片复合材料制备技术
WO2020220047A1 (fr) * 2019-04-26 2020-10-29 Thomas Jefferson University Encre durable à base de biocharbon présentant des propriétés conductrices
KR20210038376A (ko) * 2019-09-30 2021-04-07 주식회사 엘지화학 스티렌-공액디엔계 중합체 고무 조성물
KR20210092392A (ko) * 2020-01-16 2021-07-26 경상국립대학교산학협력단 리그닌 유래 활성탄의 제조방법 및 이에 따라 제조된 활성탄을 포함하는 고분자 복합재료

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