WO2013129215A1 - Particules composites de résine/inorganiques et leur procédé de production - Google Patents

Particules composites de résine/inorganiques et leur procédé de production Download PDF

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Publication number
WO2013129215A1
WO2013129215A1 PCT/JP2013/054271 JP2013054271W WO2013129215A1 WO 2013129215 A1 WO2013129215 A1 WO 2013129215A1 JP 2013054271 W JP2013054271 W JP 2013054271W WO 2013129215 A1 WO2013129215 A1 WO 2013129215A1
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inorganic
composite resin
inorganic composite
scale
resin particles
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PCT/JP2013/054271
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English (en)
Japanese (ja)
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西村修平
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日本エクスラン工業株式会社
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Priority to JP2014502157A priority Critical patent/JP6213458B2/ja
Publication of WO2013129215A1 publication Critical patent/WO2013129215A1/fr

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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
    • C09D151/00—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers
    • C09D151/10—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers grafted on to inorganic materials
    • 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
    • C09D11/10—Printing inks based on artificial resins
    • C09D11/106—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
    • C08F220/343—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate in the form of urethane links
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F292/00—Macromolecular compounds obtained by polymerising monomers on to inorganic materials

Definitions

  • the present invention relates to an inorganic composite resin particle having a novel structure and a method for producing the same.
  • Particles obtained by coating the surfaces of resin particles with metal exhibit characteristics similar to those of metal particles in terms of conductivity and design properties, and have a low specific gravity. Therefore, such particles have been used in place of metal particles in applications where metal particles have been used conventionally. In such a situation, many metal composite particles in which a metal layer is formed on the surface of resin particles in order to efficiently express metallic characteristics have been reported.
  • Patent Document 1 proposes metal-coated particles obtained by forming a metal layer by an electroless plating method after forming an inorganic particle layer on a resin powder.
  • Patent Document 2 proposes metal-coated particles having a uniform metal layer obtained by simultaneously depositing a metal and a metal oxide on a resin surface by an electroless plating method.
  • Patent Document 3 discloses particles in which resin powder and metal powder having malleability or ductility are mixed with a high shearing force and a high compressive force so that a thin metal piece is fixed on the surface of the resin powder.
  • Patent Document 4 discloses a process of coating a dispersion medium coated with paste-like colored metal flakes containing an organic solvent, and contacting the dispersion powder coated with the colored metal flakes to transfer the colored metal flakes to the resin powder. The resin powder to which the colored metal flakes were attached obtained through the step of attaching is disclosed.
  • JP-A-4-228503 Japanese Patent Laid-Open No. 7-18455 JP-A-4-50235 JP 2001-181576 A
  • an object of the present invention is to provide inorganic composite resin particles to which scale-like inorganic substances are adhered while maintaining an independent shape, and a method for producing the same.
  • the above object of the present invention is achieved by the following means.
  • the inorganic composite resin particle according to (1) which is obtained by polymerizing a vinyl monomer in the presence of a scale-like inorganic substance.
  • the vinyl monomer includes a vinyl monomer having at least one group selected from the group consisting of an isocyanate group, a blocked isocyanate group, a uretdione group, and an isocyanurate group ( Inorganic composite resin particles according to 2).
  • a mixture of a vinyl monomer having a solubility in water of less than 5% by weight, a polymerization initiator and a scale-like inorganic substance is dispersed in an aqueous medium, and a water-soluble amine compound is added, followed by suspension polymerization.
  • the method for producing inorganic composite resin particles according to any one of (1) to (6) wherein: (8) A coating composition containing the inorganic composite resin particles according to any one of (1) to (6). (9) An ink composition comprising the inorganic composite resin particles according to any one of (1) to (6). (10) A resin molded product containing the inorganic composite resin particles according to any one of (1) to (6).
  • the resin particles having the metal layer on the surface can be easily produced without going through a complicated process by combining the metals at the production stage of the resin particles.
  • the scale-like inorganic substance maintains an independent shape, a large number of plane surfaces that are specularly reflected are generated on the surface, and the surface that specularly reflects light. Characteristics, i.e., glitter, can be obtained.
  • Such inorganic composite resin particles are structurally completely different from conventional metal-coated particles obtained by various plating treatments and kneading treatments, and are expected to be used in various applications.
  • the inorganic composite resin particles of the present invention can be produced easily and at low cost.
  • FIG. 1 is an SEM image of the appearance of the inorganic composite resin particles obtained in Example 1.
  • FIG. 2 is an SEM image of the surface of the inorganic composite resin particles obtained in Example 1.
  • FIG. 3 is a cross-sectional image of the inorganic composite resin particles obtained in Example 1.
  • FIG. 4 is an SEM image of the appearance of the inorganic composite resin particles obtained in Example 5.
  • FIG. 5 is an SEM image of the surface of the resin particles obtained in Comparative Example 1.
  • inorganic composite resin particles of the present invention scaly inorganic substances are attached to the surfaces of the resin particles, and the scaly inorganic substances are in a state of maintaining independent shapes on the particle surface. .
  • the state in which the flaky inorganic substance maintains an independent shape means that the flaky inorganic substance does not fuse with other flaky inorganic substances, and each flaky inorganic substance has an independent shape. Specifically, it indicates a state as shown in FIG. 2 or FIG. In the present invention, when the scale-like inorganic substance adheres to the particles, it does not receive a strong force, so that the scale-like inorganic substance is attached to the particles while maintaining its original shape and can be in this state. It is considered a thing.
  • the shape of the inorganic composite resin particles of the present invention is not particularly limited. However, when used as an additive to a paint or resin, etc., from the viewpoint of uniform mixing and obtaining a uniform appearance, FIG. It is desirable to have a spherical shape or a shape close to a spherical shape, and a narrow particle size distribution is preferable.
  • the size of the inorganic composite resin particles of the present invention is not particularly limited, but is preferably selected in consideration of the size of the scale-like inorganic substance from the viewpoint of attaching the scale-like inorganic substance.
  • the size of the inorganic composite resin particles of the present invention is preferably 5 to 1000 ⁇ m, more preferably 10 to 1000 ⁇ m, and even more preferably 50 to 1000 ⁇ m as an average particle size. If the average particle diameter exceeds 1000 ⁇ m, it can be produced, but the application may be limited.
  • the average particle size (d50) of the scaly inorganic material employed in the present invention is preferably 5 to 100 ⁇ m, more preferably 10 to 50 ⁇ m, and even more preferably 15 to 50 ⁇ m.
  • the average thickness is 0.01 to 5 ⁇ m, more preferably 0.1 to 2 ⁇ m. If the average particle diameter is less than 5 ⁇ m, the light may be irregularly reflected to obtain glitter, and it is difficult to produce industrially. On the other hand, when it exceeds 50 ⁇ m, problems such as dropping off in the process of producing inorganic composite resin particles tend to occur. On the other hand, when the average thickness is less than 0.01 ⁇ m, the scaly inorganic material is easily broken in the production process. When the average thickness exceeds 5 ⁇ m, the scale-like inorganic substance may not be stably attached.
  • a scale-like inorganic substance is so preferable that specific gravity is small.
  • the specific gravity is preferably 1 to 5, and more preferably 1 to 3.
  • the inorganic substance is localized on the surface of the monomer droplets by selecting such an inorganic substance having a small specific gravity. It is possible to produce inorganic composite resin particles that are easy to be converted and that the characteristics of the inorganic material are remarkable.
  • the type of scale-like inorganic substance is not particularly limited as long as the desired designability is obtained, and examples thereof include metals, metal compounds, and clay minerals.
  • the metal include copper, nickel, tin, gold, silver, aluminum, iron, titanium, stainless steel, and composite materials thereof.
  • vinyl Aluminum is preferred when selecting a means for combining by suspension polymerization from the viewpoint of a small specific gravity difference from the monomer. Further, by using a resin-coated metal surface in advance, the affinity with the vinyl monomer is improved and the polymerization can be performed stably.
  • the clay mineral include layered silicate minerals, and natural mica and synthetic mica are preferably used.
  • the complex amount of the scale-like inorganic substance is preferably 0.1 to 50% by weight, more preferably 0.5 to 10% by weight, and further preferably 1 to 5% by weight based on the weight of the resin portion of the particles. %.
  • the composite amount is less than 0.1% by weight, the glitter may not be obtained.
  • the composite amount is more than 50% by weight, the amount of inorganic substances not combined with the resin increases, which is not only useless but also scaly from the surface. In some cases, the inorganic matter is easily peeled off.
  • the resin in the inorganic composite resin particles of the present invention is not particularly limited, and a resin suitable for obtaining desired characteristics may be selected.
  • a vinyl polymer is used. It is desirable to adopt.
  • the vinyl polymer has an advantage that it is easy to obtain desired characteristics because there are many types of vinyl monomers and the composition can be easily adjusted.
  • the method for producing the inorganic composite resin particles of the present invention is not particularly limited, but from the viewpoint of attaching the scaly inorganic substance while maintaining an independent shape, the vinyl monomer is added in the presence of the scaly inorganic substance. A method of polymerization is preferred.
  • a more preferable method is a method in which a mixed liquid of a vinyl monomer, a polymerization initiator, and a scaly inorganic substance is dispersed in an aqueous medium, and after adding a water-soluble amine compound, suspension polymerization is performed.
  • the scaly inorganic substance floats by convection or surface tension accompanying the volatilization of the vinyl monomer, and the affinity between the water-soluble amine compound added later and the scaly inorganic substance It is considered that the scale-like inorganic material is localized at the interface between the vinyl monomer droplet and the aqueous medium in combination with the effect of the polymerization. It is expected that adhered inorganic composite resin particles will be obtained. Hereinafter, this method will be described in detail.
  • a mixed liquid containing a vinyl monomer as a raw material, a scale-like inorganic substance, and a polymerization initiator is prepared.
  • this mixed liquid is finely dispersed in water by stirring or the like, thereby forming vinyl monomer droplets containing a scale-like inorganic substance.
  • stirring conditions and the like are set, and the size of the droplets is adjusted.
  • a water-soluble amine compound is added, then heating is started and suspension polymerization proceeds to obtain the inorganic composite resin particles of the present invention. .
  • the method for adding the water-soluble amine compound is not particularly limited, but it is desirable that the water-soluble amine compound is added in the stage before full-scale polymerization proceeds by heating. That is, by adding a water-soluble amine compound in the initial stage of polymerization, the scaly inorganic substance is localized in the vicinity of the surface of the vinyl monomer droplet, and then polymerized particles are formed. It becomes possible.
  • the addition amount of the water-soluble amine compound is 0.1 to 10% by weight, preferably 0.5 to 5% by weight, more preferably 1 to 3% by weight based on the vinyl monomer.
  • the addition amount is less than 0.1% by weight, the effect of localizing the scaly inorganic substance on the surface of the vinyl monomer droplets is weakened, and the inorganic composite resin particles of the present invention cannot be obtained and agglomerated. Agglomerated particles may be obtained.
  • the addition amount is more than 10% by weight, the viscosity may be excessively increased and polymerization may not be performed stably.
  • water-soluble amine compounds include ammonia, hydrazine, methylamine, dimethylamine, trimethylamine, ethylamine, diethylamine, triethylamine, ethylenediamine, ethanolamine, allylamine, ethanolamine, diethanolamine, triethanolamine, aniline, polyallylamine, polyethylene
  • water-soluble amine compounds include ammonia, hydrazine, methylamine, dimethylamine, trimethylamine, ethylamine, diethylamine, triethylamine, ethylenediamine, ethanolamine, allylamine, ethanolamine, diethanolamine, triethanolamine, aniline, polyallylamine, polyethylene
  • imine and polyvinylamine include imine and polyvinylamine.
  • polymer type polymers such as polyallylamine, polyethyleneimine, and polyvinylamine are preferable because polymerization can be performed more stably.
  • vinyl monomers examples include acrylate monomers such as methyl acrylate, ethyl acrylate, 2-ethylhexyl acrylate, lauryl acrylate, dimethylaminoethyl acrylate, diethylaminoethyl acrylate, methyl methacrylate, Methacrylic acid ester monomers such as ethyl methacrylate, lauryl methacrylate, dimethylaminoethyl methacrylate, styrene monomers such as styrene and p-methylstyrene, alkyl vinyl ethers such as methyl vinyl ether and ethyl vinyl ether, vinyl acetate, butyric acid Vinyl ester monomers such as vinyl; N-alkyl substituted (meth) acrylamides such as N-methylacrylamide and N-ethylacrylamide; nitrile monomers such as acrylonitrile and methacrylonitrile; Polyfunctional monomers such as x
  • scale-like inorganic substances can be more stably attached, which is particularly preferable. This effect is due to the reaction between these vinyl monomers and the water-soluble amine compound in the state where the scale-like inorganic substance is localized on the droplet surface by the water-soluble amine compound added later. It is thought that it may be more stabilized.
  • the amount of the vinyl monomer having an isocyanate group or a functional group that generates an isocyanate group is preferably 0.1 to 3% by weight, more preferably, based on the total weight of the vinyl monomer used. Is 0.5 to 2% by weight.
  • Examples of the functional group that generates an isocyanate group include a blocked isocyanate group, a uretdione group having a structure in which the isocyanate group is dimerized, and an isocyanurate group having a structure in which the isocyanate group is trimerized.
  • examples of these vinyl monomers are not particularly limited, but when a production method in which polymerization is performed in an aqueous medium such as aqueous suspension polymerization is employed, reaction with water is suppressed.
  • a vinyl monomer having a blocked isocyanate group, a uretdione group, an isocyanurate group, or the like is preferable.
  • Such monomers include ethoxylated isocyanuric acid triacrylate, ⁇ -caprolactone modified tris- (2-acryloxyethyl) isocyanurate, isocyanuric acid ethylene oxide modified di (meth) acrylate, isocyanuric acid ethylene oxide modified tri (meth).
  • the amount of the scale-like inorganic substance added may be an amount that can generally cover the particle surface from the viewpoint of obtaining glitter, and the vinyl monomer as described in the above-mentioned range of the composite amount of the scale-like inorganic substance. Is preferably 0.1 to 50% by weight, more preferably 0.5 to 10% by weight, and still more preferably 1 to 5% by weight. If the amount of scale-like inorganic substance added is too small, there may be a problem that resin particles that do not contain any scale-like inorganic substance are partially produced. When the addition amount of the scale-like inorganic substance becomes excessive, there may be a problem that the inorganic substance falls off from the surface of the resin particles.
  • the inorganic composite resin particles of the present invention described above can be used, for example, as an additive for giving an appearance having metallic luster to a resin molded product as well as a paint and an ink composition.
  • Most of the inorganic composite resin particles of the present invention are composed of a resin and have a small specific gravity. Therefore, even when added to a paint or the like, the inorganic composite resin particles have an advantage that they are less likely to settle than metal particles.
  • Examples of a method for producing such a paint or ink composition include a method of adding the inorganic composite resin particles and the binder resin of the present invention to an organic solvent.
  • the binder resin is not particularly limited, and examples thereof include thermoplastic resins, thermosetting resins, and photocurable resins. Specifically, acrylic resins, polyester resins, polyvinyl chloride, polyurethane, silicone Examples thereof include resins and melamine resins.
  • an acrylic resin, an acrylic-silicone resin, or the like can be suitably used.
  • the organic solvent is not particularly limited as long as it dissolves the binder resin.
  • examples include ether (ethyl cellosolve), ethyl acetate, butyl acetate, isopropyl alcohol, acetone, and anisole. These may be used alone or in combination of two or more.
  • various additives such as coloring agents, such as a leveling agent, a surface modifier, a defoaming agent, and a pigment, may be added to this coating material and ink composition.
  • the inorganic composite resin particles of the present invention are added, and then a sand mill, a ball mill, an attritor, a high-speed rotary stirring device, three A method of uniformly dispersing and mixing using a roll or the like can be mentioned.
  • the inorganic composite resin particles of the present invention are not limited to organic solvent-based paints and ink compositions as described above, and can be used for various paints and ink compositions such as solvent-free, water-based, and powder. .
  • thermoplastic or thermosetting resin examples include a polymethyl methacrylate resin, an MS resin, a polycarbonate resin, and a polyester resin.
  • a resin having excellent transparency, good weather resistance, and rigidity is preferably used.
  • Examples of a method for producing such a resin molded product include a method in which a resin and an inorganic composite resin particle are mixed with a mixer, kneaded with a melt kneader, and then extruded to obtain a resin molded product such as a sheet. Further, it is possible to adopt a method of taking out as pellets after melt-kneading, and injection-molding the pellets after melting.
  • the coating film or molded article prepared as described above has a number of planar surfaces that are mirror-reflected on the surface and contains the inorganic composite resin particles of the present invention having a glittering property. Appearance with excellent glitter.
  • Example 1 The reaction vessel was charged with 500 parts by weight of water, and then 3 parts by weight of polyvinyl alcohol was dissolved. To this aqueous solution, 150 parts by weight of methyl methacrylate, 10 parts by weight of ethylene glycol dimethacrylate, 1 part by weight of ethoxylated isocyanuric acid triacrylate, aluminum paste manufactured by Asahi Kasei Chemicals Corporation (GX-40A, average particle diameter 19 ⁇ m, specific gravity 1.7) 15 A mixed solution of 1 part by weight of 2,2′-azobis (2-methylvaleronitrile) was added to maintain the dispersion state under constant stirring, and after adding 2 parts by weight of polyethyleneimine, 60 ° C. For 5 hours to conduct suspension polymerization. The obtained suspension was filtered, washed with water and dried, and then classified with a vibration classifier to obtain inorganic composite resin particles of Example 1. The average particle diameter of the particles was 250 ⁇ m.
  • FIGS. 3 images of the appearance, surface and cross section of the inorganic composite resin particles of Example 1 are shown in FIGS. From these images, it was confirmed that in the obtained inorganic composite resin particles, scale-like metals were adhered in a state of maintaining independent shapes. Moreover, the metal was not contained inside the particles. In FIG. 3, what appears white inside the particles is that the scale-like metal formed on the back side of the resin (that is, the back side of the image) is seen through.
  • Example 2 Inorganic composite resin particles of Example 2 were obtained in the same manner as Example 1 except that ethoxylated isocyanuric acid triacrylate was not used. The average particle size of the particles was 269 ⁇ m. Moreover, in the SEM image of this particle
  • Example 3 Except for using 15 parts by weight of aluminum paste (HR-40A, average particle diameter 19 ⁇ m, specific gravity 1.4, resin coat type) manufactured by Asahi Kasei Chemicals Corporation instead of 15 parts by weight of aluminum paste (GX-40A) In the same manner as in Example 1, inorganic composite resin particles of Example 3 were obtained. The average particle diameter of the particles was 302 ⁇ m. Moreover, in the SEM image of this particle
  • Example 4 Resin particles of Example 4 were obtained in the same manner as Example 1 except that the amount of aluminum paste (GX-40A) added was changed to 85 parts by weight. The average particle size of the particles was 1025 ⁇ m. Moreover, in the SEM image of this particle
  • Example 5 instead of 15 parts by weight of aluminum paste (GX-40A), 15 parts by weight of pearl pigment (LIMINA EXTEROROR PEARL RADIANCE 1303D, mica coated with rutile titanium oxide, average particle diameter of 21 ⁇ m, specific gravity of 2.8) manufactured by BASF is used. Except for this, resin particles of Example 5 were obtained in the same manner as Example 1. The average particle diameter of the particles was 67 ⁇ m. Moreover, as shown in FIG. 4, in the SEM image of this particle
  • pearl pigment LIMINA EXTEROROROR PEARL RADIANCE 1303D, mica coated with rutile titanium oxide, average particle diameter of 21 ⁇ m, specific gravity of 2.8
  • Comparative Example 1 Resin particles of Comparative Example 1 were obtained in the same manner as Example 1 except that no polyethyleneimine was added. When an SEM image of the obtained particles was observed, as shown in FIG. 5, the scaly metal was submerged inside the particle, and the scaly metal was not attached. In addition, a large number of particles were partially fused to form an irregular shape.
  • Comparative Example 2 Resin particles of Comparative Example 2 were obtained in the same manner as in Example 1 except that the amount of aluminum paste (GX-40A) added was changed to 0.01 parts by weight. When SEM images of the obtained particles were observed, many resins in which no metal was combined were observed.

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  • Chemical & Material Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Pigments, Carbon Blacks, Or Wood Stains (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Polymerisation Methods In General (AREA)
  • Processes Of Treating Macromolecular Substances (AREA)
  • Paints Or Removers (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)

Abstract

La présente invention concerne des particules composites de résine/inorganiques qui comprennent chacune une particule de résine et des flocons inorganiques adhérant à sa surface. Lesdites particules composites de résine/inorganiques se caractérisent en ce que les flocons inorganiques conservent des formes indépendantes les unes des autres. L'invention a trait également à un procédé permettant de produire simplement les particules composites de résine/inorganiques. Les particules composites de résine/inorganiques présentent une luminosité, ce qui leur permet d'être largement utilisées dans les matériaux de revêtement, les compositions d'encre, les moulages en résine, etc.
PCT/JP2013/054271 2012-02-29 2013-02-21 Particules composites de résine/inorganiques et leur procédé de production WO2013129215A1 (fr)

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JP2012-043803 2012-02-29
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPWO2018096964A1 (ja) * 2016-11-25 2018-12-27 東レ株式会社 ポリブチレンテレフタレート樹脂粒子の製造方法およびポリブチレンテレフタレート樹脂粒子
WO2020045184A1 (fr) * 2018-08-30 2020-03-05 日本エクスラン工業株式会社 Matériau porogène pour la fabrication d'un filtre céramique poreux

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JPS5294389A (en) * 1976-02-04 1977-08-08 Mitsui Toatsu Chem Inc Production of granulated moldable composite
JPS56103235A (en) * 1980-01-22 1981-08-18 Kanegafuchi Chem Ind Co Ltd Composite vinyl chloride resin composition and its preparation
JPS60228505A (ja) * 1984-04-24 1985-11-13 Chisso Corp 塩化ビニル系重合体組成物の製造方法
JPH02300205A (ja) * 1989-05-16 1990-12-12 Nippon Shokubai Kagaku Kogyo Co Ltd 磁性体含有球状微粒子、その製造方法およびその用途
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JPWO2018096964A1 (ja) * 2016-11-25 2018-12-27 東レ株式会社 ポリブチレンテレフタレート樹脂粒子の製造方法およびポリブチレンテレフタレート樹脂粒子
WO2020045184A1 (fr) * 2018-08-30 2020-03-05 日本エクスラン工業株式会社 Matériau porogène pour la fabrication d'un filtre céramique poreux
JP6701540B1 (ja) * 2018-08-30 2020-05-27 日本エクスラン工業株式会社 多孔質セラミックフィルタ製造用造孔材

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