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WO1999021662A1 - Modification des surfaces de solides polymeres - Google Patents

Modification des surfaces de solides polymeres Download PDF

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Publication number
WO1999021662A1
WO1999021662A1 PCT/US1998/022308 US9822308W WO9921662A1 WO 1999021662 A1 WO1999021662 A1 WO 1999021662A1 US 9822308 W US9822308 W US 9822308W WO 9921662 A1 WO9921662 A1 WO 9921662A1
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WO
WIPO (PCT)
Prior art keywords
resins
gas
particulate solids
resin
pressure
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.)
Ceased
Application number
PCT/US1998/022308
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English (en)
Inventor
Douglas S. Richart
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Individual
Original Assignee
Individual
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Individual filed Critical Individual
Publication of WO1999021662A1 publication Critical patent/WO1999021662A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29B—PREPARATION OR PRETREATMENT OF THE MATERIAL TO BE SHAPED; MAKING GRANULES OR PREFORMS; RECOVERY OF PLASTICS OR OTHER CONSTITUENTS OF WASTE MATERIAL CONTAINING PLASTICS
    • B29B9/00—Making granules
    • B29B9/16—Auxiliary treatment of granules
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D7/00—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials
    • B05D7/02—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials to macromolecular substances, e.g. rubber
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C59/00—Surface shaping of articles, e.g. embossing; Apparatus therefor
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C71/00—After-treatment of articles without altering their shape; Apparatus therefor
    • B29C71/009—After-treatment of articles without altering their shape; Apparatus therefor using gases without chemical reaction
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/12—Powdering or granulating
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/12—Powdering or granulating
    • C08J3/16—Powdering or granulating by coagulating dispersions
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/20—Compounding polymers with additives, e.g. colouring
    • C08J3/203—Solid polymers with solid and/or liquid additives
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D2401/00—Form of the coating product, e.g. solution, water dispersion, powders or the like
    • B05D2401/90—Form of the coating product, e.g. solution, water dispersion, powders or the like at least one component of the composition being in supercritical state or close to supercritical state
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C71/00—After-treatment of articles without altering their shape; Apparatus therefor
    • B29C71/0009—After-treatment of articles without altering their shape; Apparatus therefor using liquids, e.g. solvents, swelling agents
    • B29C2071/0054—Supercritical fluid treatment, i.e. using a liquid in which distinct liquid and gas phases do not exist
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids

Definitions

  • This application relates to methods and means for modifying the surfaces of particulate solid polvmers. More particularly, the invention relates to methods and means for tackifving the surfaces of polymeric materials variously to adhere solids to their surfaces, to alter their surface geometry and to achieve controlled agglomeration of the particulate solids.
  • the invention finds particular utility, for example, in preparing polymeric compositions in which pigments, metal powders and flakes, catalysts, silica, mica, charge control agents and other particulate solids are adhered to the surfaces of the compositions.
  • the compositions may be used in fusion coating processes including those which utilize electrostatic deposition.
  • Another suggested field of use of the invention is in the preparation of electrostatic toners and pharmaceuticals in which solid active ingredients are adhered to particulate polymers, carriers or diluent materials.
  • the invention is described with particular regard to the formulation of coating powders for use in fusion coating processes although it should be understood that it is not intended that the invention be so limited. Background Art
  • Coating powders are widely used in fusion coating processes in which decorative and protective coatings are applied to metals and other substrates.
  • Coating powders are usually based on thermosetting resin systems comprising a resin, curing agents or another co-reactable resin, additives to control surface tension, gloss, resistance to light and heat, pigments and fillers to control color and reduce cost, and catalvsts to reduce the temperature required for curing or to promote faster curing at a higher temperature.
  • thermosetting resin systems comprising a resin, curing agents or another co-reactable resin, additives to control surface tension, gloss, resistance to light and heat, pigments and fillers to control color and reduce cost, and catalvsts to reduce the temperature required for curing or to promote faster curing at a higher temperature.
  • Today coating powders are usually made in melt mixing processes in which all the ingredients are thoroughly mixed and dispersed at elevated temperature above the melting point of the base resins, typically in a mixing extruder. The extrudate is cooled, broken into coarse chips and then ground to a fine powder, as in an air impact mill. Typical coating powders have a median particle size of about 30 - 35 ⁇ m and have no particles larger than about 180 ⁇ m. Powders made by this method are substantially uniform in that each particle contains the starting ingredients in the proportions in which they were initially included in the formulation. The temperatures at which coating powders are mixed, transported and stored and used in fusion coating processes impose a number of requirements.
  • coating powders should have a glass transition temperature, Tg, of at least about 50°C, and preferably higher.
  • Coating powders which have low melt viscosities at comparatively low temperatures find utility, for example, in the application of clear coats in automotive applications. Typicallv, a clear coat is applied over plastic or other components which can be harmed at high curing temperatures.
  • powders which cure at comparatively low temperatures are desired, for example, the coating of heat sensitive articles or assemblies that contain wood, rubber or plastic components. Catalysts are used to increase the rate at which the resin will cure at low temperatures, but they can only be used at relatively low levels.
  • the curing reaction may proceed too rapidly in the mixing extruder, leading to an undesirable increase in melt viscositv and loss of flow in the final powder.
  • excessive cross linking in the extruder will cause gelation of a thermosetting mixture rendering it useless in powder coating processes.
  • Thermosetting coating powders that are too reactive at low temperatures may react under ambient conditions while being transported or stored.
  • the melt flow of reactive powders may continue to decrease over a matter of days or several months, to the point where they will no longer adequately flow during application.
  • Even currently available commercial powders show a decrease in flow during storage to some degree and the useful life is typicallv about one year.
  • Very reactive powders, such as those in coating pipe and reinforcing bars (rebar) have a more limited storage life and may require refrigerated shipping and storage.
  • the ability of a powder to retain good melt flow characteristics during storage is frequently referred to as storage stability.
  • conductive solids like carbon black may be incorporated into the coating powders.
  • the conductive carbon particles are more effective in reducing resistivity if the carbon particles are adhered to the surface of the coating powders rather than being melt mixed in and encapsulated by the insulating coating powders.
  • the triboelectric charging characteristics of a powder is improved if a triboelectric additive is adhered to the surface of and not encapsulated in the coating powders since the tribo-electrification of a particle occurs only on its surface.
  • Aluminum, mica, silica, glass and pigment flakes are used to formulate coating powders that will exhibit a metallic appearance.
  • these solids are encapsulated in the coating powders, their decorative effectiveness will be concealed. Further, if mixed with the coating powders under conditions of high shear, as in a mixing extruder, the flakes can be ground into such small particles that the metallic effect provided by the solid in flake form is lost and the finish that results from such a coating powder has a dull, gray appearance.
  • the powder that is not deposited on a substrate is collected in a reclamation system and recycled by mixing the over-spray with virgin coating powders.
  • metal flakes When metal flakes are loosely mixed with and segregate from the coating powders, the flakes are not charged to the same extent or deposited at the same rate as the coating powders. Over a period of time, the amount of flake in the coating powders will continually increase until a point is reached at which the high concentration of metal flakes interferes with the charging mechanism. If the powder in the ionized field becomes too conductive, the electrostatic gun may "short out.” Further, the appearance of the coatings will change as the ratio of flakes to powder changes.
  • U.K. Patent Specification 1 ,404,556 describes coating powders in which aluminum flakes are imbedded into the powder by milling, e.g, in a ball-mill. Since the flakes may be significantly fragmented, the coating powders produced by this method do not achieve the luster of comparable solvent-based metallic paints.
  • U.S. Pat. 3,632,369 discloses a method of mixing dry plastic particles with dry pigments in a high-speed mixer. By maintaining the mixer blades blade at a high angular velocity, the pigment is adheres to the plastic without agglomerating the particles.
  • U.S. Pat. No. 4, 197,35 1 describes brush polishing a dry mixture of metal flakes and plastic powder so as to embed the flakes into the powder. Although the coating powder obtained may have a high luster, the brush polishing method described in this patent is impractical for industrial scale production of coating powders.
  • U.S. Pat. 4,598,006 is an impregnation process in which active agents are impregnated into pharmaceutical compounds by use of swelling agents.
  • U.S. Pat. 4,820,752 discloses a method of infusing an additive into a polymer by using a compressed fluid that is normally a gas at room temperature. The polymer has some degree of solubility in the compressed gas.
  • U.S. Pat. 5, 187,220 adheres a flake material to the surface of coating powders that have been softened by heating the coating powders to close to their melting point. Sufficient mechanical shear is imparted to prevent the agglomeration of the coating powders.
  • U.S. Patent 5,470,893 discloses a method in which composite particles are formed by the agglomeration of individual particles bv mechanical means. Summary of the Invention It's an object of this invention is to prepare coating powders which cure at lower temperatures but which can be processed, prior to the addition of catalysts and accelerators, by usual techniques in a mixing extruder.
  • Another object of this invention is to allow the preparation of more reactive coating powders, which cure rapidly at elevated temperatures but have good storage stability.
  • a further object of this invention is to adhere catalysts, metal flakes, pigments, conductive solids and flake pigments, to the surface of fusion coating powders.
  • Another object of the invention is to alter the conductivity, tri bo-electric charging characteristics and surface appearance of fusion coating powders and the coatings made from the coating powders.
  • Yet another object of the invention is to make efficient utilization of particulate materials in altering the surface properties of fusion coating powders and the coatings made from the coating powders.
  • Another object of this invention is alter the surface geometry of fusion coating powders to make them more nearly spherical.
  • Another object of this invention is to agglomerate fusion coating powders under controlled conditions to form larger particles from smaller panicles.
  • the "supercrital range" is used to mean those conditions of temperature and pressure at which material that is a gas at room temperature is at, or sufficiently close to, its supercritical phase to be effective to tackifv the surfaces of resins by partial solvation of resins.
  • the solids are contacted while the surfaces of the powders are tacky.
  • the process is discontinued by changing the pressure or temperature conditions to remove the gas from its supercritical range by bleeding the gas awav from the powders. This results in non-tacky, free flowing powders which have altered surface characteristics, that is the surfaces may more nearly approach a spherical shape without jagged corners or the powders may have solids adhered to their surfaces.
  • the invention is based on the fact that many gases, while in their supercritical range, solvate the surface of resin particles and make them tacky.
  • the maximum solvating power of gases is observed at the supercritical phase of the gases but significant solvating power is also observed at conditions approaching the supercritical phase. It is usually easier to conduct the solvation of powders in this invention at ambient temperature conditions to avoid heating or cooling of the treatment vessel.
  • the treatment gas is carbon dioxide
  • the supercritical range begins at room temperature (i.e. about 20° C) and at pressure of about 820 psi.
  • any temperature or pressure above these given values for carbon dioxide can be exceed while staying within the defined "supercritical range.” Under these conditions the resin particles will not adhere to each other provided a sufficient amount of agitation (kinetic energy) is imparted to the resin particles.
  • the lowest possible temperature and pressure should be used, together with the shortest possible processing time, so as to adhere the additives to the surface of the particles without diffusing them into the interior of the particles.
  • Fig. 1 is a photomicrograph of a resin mixture prior to treatment in accordance with this invention.
  • Fig. 2 is a photomicrograph of a resin mixture after it has been treated in accordance with this invention. Detailed Description of the Drawings
  • Both of the figures are photomicrographs taken with a Leica NH-T confocal microscope utilizing an ultraviolet primary laser and a secondary laser in the range at a magnification of 225x.
  • the two lasers are used to take sectional photomicrographs and the sections are assembled to construct a composite with a greater depth of field.
  • the white (or blank) and sometimes shiny spots in the photomicrographs are aluminum flakes and the other objects that appear in the photomicrographs are resin particles.
  • Fig. 1 is a photomicrograph taken of the resin mixture (i.e. epoxy coating powder and aluminum flake )of Example 3 before the mixture was treated in accordance with the method of this invention.
  • the photomicrograph clearly shows a number of manv discrete aluminum particles (white spots) that are not associated with any resin particles. Further, attention is called to the form and size of the resin particles. They are distinguished by the large size differences and the presence of manv very small particles. It can be observed that the resin particles are irregular in shape and have many sharp edges.
  • the size and configuration of the resin particles here viewed is typical of the characteristics of ground resins powders.
  • Fig. 2 is a photomicrograph taken of the resin blend that was formed bv the process of Example 3. Here it can be seen that their are no free aluminum particles that they all have adhered to the resins during the treatment with liquid carbon dioxide. Additional benefits were obtained by the use of the process of Example 3. Note that agglomerates have been formed and that there is almost a total absence of the very fine particles that are seen in Fig. 1. Finally, note how the configuration of the particles have changed in that most of the edges have been rounded and are not sharp like those of Fig. 1.
  • EXAMPLE I 10 g. of powder chips of a coating powder resin mixture compounded in a mixing extruder were thoroughly mixed with 0.38 g. of aluminum powder flake designated LE 2993 AR from Silberline Manufacturing Co.
  • the powder chips approximately 2-5 mm thick and ranging in size from about 0. 1 to about 2.0 mm were prepared on a conventional melt mixing extruder and flaker based on a standard coating powder composition comprising epoxy resins, a phenolic curative, an acrylic flow control additive, pigments and fillers.
  • the mixture of coating powder chips and aluminum powder were charged into the center of a 50 ml capacity extraction cylinder. At each end of the cylinder, polypropylene fiber packing was inserted occupying approximately 20% of the cylinder volume.
  • End plugs with a threaded hole for attachment high pressure tubing, were screwed in each end of the cylinder until pressure tight.
  • Tubing with pressure fittings were connected through a valve to a carbon dioxide cylinder, to the bottom plug of the extraction cylinder. Similar tubing was connected to the top of the cylinder and to a flow r meter subsequently vented to the atmosphere.
  • the cylinder is mounted in an oven so its temperature can be controlled between ambient and approximately 120° C.
  • the outlet valve of the carbon dioxide cylinder was opened and the inlet valve to the extraction opened and adjusted to give a gas flow rate through the apparatus of 3 liters per minutes
  • the liquid carbon dioxide was delivered from the cylinder at ambient temperature, 25° C, and cylinder pressure, 820 psi, and allowed to flow through the extraction cylinder for 30 minutes. After 30 minutes, the flow of carbon dioxide was stopped by closing the inlet valve and the pressure in the cylinder allowed to dissipate at a flow rate of 3 - 5 1/min. until it was at atmospheric pressure.
  • the high pressure tubing was removed from the extraction cylinder, the cylinder removed from the oven and the cylinder opened by removing the end caps.
  • Example I The procedure of Example I was repeated except that 10 g. of a powder prepared by grinding the resin mixture chips was mixed with 0.30 g. of aluminum powder.
  • the powder had an average particle size of 30 - 35 ⁇ m and all particles passed through a 100 mesh screen. After 30 minutes exposure to carbon dioxide flowing at 31/min., at a temperature of 24° C. and 820 psi, the cylinder was opened and the powder mixture with aluminum flakes examined. In this case, the powder had agglomerated to form a solid plug which could only be broken apart with some difficulty.
  • the reactor was opened and the coating powder with aluminum flakes recovered. On examination under 10X magnification, many aluminum flakes were attached to epoxy powder particles and could not be removed by mechanical manipulation. Some of the powder particles were slightly agglomerated but were easily broken up by light agitation to their original size.
  • EXAMPLE 4 A trial was carried out as in Example 3 except only 160 g. epoxy powder and 3% aluminum flake were charged to the reactor. The powder particles and aluminum flake were maintained in contact with each other by stirring at 600 rpm for 10 minutes at ambient temperature and a pressure of 800 psig. The vessel was depressurized over a period of 4 minutes with no agitation. As in Example 3, aluminum particles were firmly attached to the epoxv nowder particles and could not be separated bv rubbing. There was no agglomeration of the particles,

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Plasma & Fusion (AREA)
  • Mechanical Engineering (AREA)
  • Dispersion Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Paints Or Removers (AREA)
  • Pigments, Carbon Blacks, Or Wood Stains (AREA)

Abstract

On rend adhésives les surfaces de particules polymères en les mettant en contact avec un liquide qui est normalement un gaz à température ambiante. Ce gaz se trouve dans sa phase supercritique ou est proche de sa phase supercritique (à savoir, dans une plage supercritique) et on modifie les surfaces rendues adhésives de ces polymères par adhérence diversifiée de solides sur leurs surfaces, par modification de leur géométrie de surface ou par augmentation de leur dimension sous l'effet d'une agglomération contrôlée.
PCT/US1998/022308 1997-10-25 1998-09-21 Modification des surfaces de solides polymeres Ceased WO1999021662A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US95875197A 1997-10-25 1997-10-25
US08/958,751 1997-10-25

Publications (1)

Publication Number Publication Date
WO1999021662A1 true WO1999021662A1 (fr) 1999-05-06

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PCT/US1998/022308 Ceased WO1999021662A1 (fr) 1997-10-25 1998-09-21 Modification des surfaces de solides polymeres

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1197513A3 (fr) * 2000-10-10 2002-05-08 Kao Corporation Procédé pour préparer des particules composites
US6858369B1 (en) * 2000-04-27 2005-02-22 Sharp Kabushiki Kaisha Toner and manufacturing method thereof
CN108422581A (zh) * 2018-05-28 2018-08-21 林宗良 一种制造球形塑料颗粒的方法

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3674736A (en) * 1969-04-15 1972-07-04 Nat Distillers Chem Corp Process for the preparation of pigmented polymer powders of controlled particle shape and size and size distribution and product
US4774137A (en) * 1984-12-22 1988-09-27 Bayer Aktiengesellschaft Synthetic resin powders for coatings with reduced surface resistance
US5399597A (en) * 1992-11-02 1995-03-21 Ferro Corporation Method of preparing coating materials
US5474803A (en) * 1991-12-25 1995-12-12 Nara Machinery Co., Ltd. Method for preparing composite particles
US5766637A (en) * 1996-10-08 1998-06-16 University Of Delaware Microencapsulation process using supercritical fluids

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3674736A (en) * 1969-04-15 1972-07-04 Nat Distillers Chem Corp Process for the preparation of pigmented polymer powders of controlled particle shape and size and size distribution and product
US4774137A (en) * 1984-12-22 1988-09-27 Bayer Aktiengesellschaft Synthetic resin powders for coatings with reduced surface resistance
US5474803A (en) * 1991-12-25 1995-12-12 Nara Machinery Co., Ltd. Method for preparing composite particles
US5399597A (en) * 1992-11-02 1995-03-21 Ferro Corporation Method of preparing coating materials
US5766637A (en) * 1996-10-08 1998-06-16 University Of Delaware Microencapsulation process using supercritical fluids

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6858369B1 (en) * 2000-04-27 2005-02-22 Sharp Kabushiki Kaisha Toner and manufacturing method thereof
EP1197513A3 (fr) * 2000-10-10 2002-05-08 Kao Corporation Procédé pour préparer des particules composites
CN108422581A (zh) * 2018-05-28 2018-08-21 林宗良 一种制造球形塑料颗粒的方法

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