WO1992003222A1 - Dispersant, substance particulaire traitee en surface, procede d'utilisation de dispersant et compositon de dispersion - Google Patents

Dispersant, substance particulaire traitee en surface, procede d'utilisation de dispersant et compositon de dispersion Download PDF

Info

Publication number
WO1992003222A1
WO1992003222A1 PCT/JP1991/001131 JP9101131W WO9203222A1 WO 1992003222 A1 WO1992003222 A1 WO 1992003222A1 JP 9101131 W JP9101131 W JP 9101131W WO 9203222 A1 WO9203222 A1 WO 9203222A1
Authority
WO
WIPO (PCT)
Prior art keywords
dispersant
polymer
medium
acid
treated
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/JP1991/001131
Other languages
English (en)
Japanese (ja)
Inventor
Shizuo Kitahara
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.)
Zeon Corp
Original Assignee
Nippon Zeon Co Ltd
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
Priority claimed from JP2224503A external-priority patent/JPH04108873A/ja
Priority claimed from JP2224502A external-priority patent/JPH04108874A/ja
Application filed by Nippon Zeon Co Ltd filed Critical Nippon Zeon Co Ltd
Publication of WO1992003222A1 publication Critical patent/WO1992003222A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
    • C08C19/00—Chemical modification of rubber
    • 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
    • C09D7/45—Anti-settling agents

Definitions

  • Dispersant surface-treated particulate matter, method of using dispersant, and dispersion composition
  • the present invention relates to a method for dispersing a particulate material, for example, a filler, a reinforcing agent, an inorganic fine particle such as a magnetic powder or a pigment, an organic pigment, and an organic fine particle such as a single fiber chip in a medium such as a solvent or a polymer.
  • the present invention relates to a dispersant, fine particles surface-treated with a dispersant, a method for using the dispersant, and a dispersion composition of the particulate matter.
  • a particulate inorganic substance such as titanium oxide or zinc oxide is blended as a pigment, and a particulate organic substance is added to a pigment or coating film. It is used as a filler.
  • inorganic substances such as calcium carbonate and silica are used as fillers and reinforcing agents.
  • Organic fine particles such as single fiber chops and granular polymers are also compounded as reinforcing agents and surface treatment agents.
  • silane coupling agents for example, silane coupling agents and titanium coupling agents.
  • metal salts of fatty acids and the like are used. The use of these compounds improves the adhesion between the two at the interface. The force dispersibility is still insufficient, and the type of applicable particulate matter is limited. .
  • an object of the present invention is to provide a novel dispersant which can be applied to various kinds of fine inorganic and organic substances and improves the dispersibility of the fine particles in a medium such as an organic medium or a polymer. .
  • Another object of the present invention is to provide a fine particle substance and a stable fine particle substance dispersion composition which are treated with the above dispersant and have improved dispersibility in various media, and provide a method of using the dispersant. It is in.
  • the present inventors have conducted intensive studies in order to achieve the above object, and as a result, have found that a specific polymer exhibits an excellent action as a dispersant for a particulate substance in various media.
  • the polymer is improved in processability, transportability, filling property, etc. in order to suppress the increase in viscosity of the system to which the particulate material has been added, and furthermore, the particulate material previously surface-treated with the polymer. Showed good dispersibility in various media.
  • the present invention has been completed based on the above findings.
  • the modified polymer (a) obtained by reacting an unsaturated polymer with an organic compound having a carboxylic acid group and an aldehyde group in the presence of a protonic acid or a Lewis acid, Polymer (mouth) of the union combined with tin compound and isoprene treated with tin tetrachloride
  • a dispersant for dispersing fine particles in a medium characterized by containing at least one polymer selected from the group consisting of: (c), a particulate material surface-treated with any of the above dispersants
  • Dispersant composition of fine particles comprising any one of the above-mentioned dispersants, fine particles and medium or dispersion of fine particles comprising a medium and a medium surface-treated with any of the above dispersants Composition provided
  • the dispersant of the present invention has a function of facilitating uniform dispersion of various inorganic and organic fine particles in various media, and also has a dispersion stabilizing function of preventing reaggregation.
  • a dispersion stabilizing function of preventing reaggregation.
  • the present invention uses a polymer obtained by the following method as a dispersant.
  • the modified polymer (a) obtained by reacting an unsaturated polymer with an organic compound having a carboxyl group and an aldehyde group in the presence of the protic acid or Lewis acid used in the present invention is disclosed in It is a compound obtained by the method described in Japanese Patent Publication No. 3802.
  • the unsaturated polymer L in the molecular chain is a polymer having a carbon-carbon double bond at the terminal of the molecular chain.
  • Examples of the polymer having the bond in the molecular chain include conjugated diene such as butadiene, isoprene, and piperylene, dicyclopentadiene, and ethylene. Homopolymers and copolymers of lidennorbornene; copolymers of conjugated gens and vinyl monomers such as polybutadiene, polyisoprene, styrene butter copolymers [random copolymers, block copolymers (A-B, A — B— Type A, etc., where A represents a polybutadiene block and B represents a polystyrene block.)], Styrene-isoprene copolymer [random copolymer, block copolymer (A-B type, A — B— Type A, etc., where A is a polyisoprene block and B is a polystyrene block.)], Acrylonitrile-butadiene copolymer, butadiene-
  • polystyrene diacrylate examples include low molecular weight polymers such as low molecular weight polyethylene, polypropylene, and oligomers of polyolefin, or oligomers; polybutene, polyethylene glycol diacrylate, and polypropylene glycol.
  • macromers such as diacrylate, polypropylene glycol dimethacrylate, polystyrene methacrylate, and polystyrene diacrylate.
  • a polymer having a carbon-carbon double bond in the molecular chain or at the molecular chain terminal may be used.
  • the molecular weight is not particularly limited, and the number average molecular weight in terms of standard polystyrene measured by GPC is 3 Oligomers from 1000 to 100,000 to high molecular weight polymers are included.
  • the organic compound having a carboxyl group and an aldehyde group to be reacted with the above polymer has at least one of each group in the molecule, and is a linear aliphatic compound having up to 20 carbon atoms, a benzene ring, Naphthalene ring, pi It is selected from compounds having an aromatic ring such as a lysine ring and a furan ring, and alicyclic compounds such as a cyclopentane ring, a cyclopentene ring and a cyclohexane ring.
  • an oxygen atom, a sulfur atom, a nitrogen atom or a multiple bond can be appropriately contained in a molecular chain.
  • the hydrogen atom in the molecule can be replaced with an arbitrary substituent such as an alkyl group, an alkoxy group, a halogen atom, a hydroxyl group, an amino group or the like as long as the reaction is not adversely affected.
  • Compounds having an aromatic ring such as 2-formylacrylic acid, 6-formylhexanoic acid, formylmethoxyacetic acid, 2-formylbutyric acid, and 3- (carboxymethoxy) propioaldehyde, are 2-, 3-, or 4-carboxy.
  • a compound having an aromatic ring in which a carboxyl group or an atomic group containing this group and an aldehyde group or an atomic group containing this group are located adjacent to each other on the ring has a higher reaction rate.
  • the amount of organic compounds containing carboxyl and aldehyde groups is It is usually 0.01 to 20 parts by weight per 100 parts by weight of the compound having a sum bond.
  • the catalyst used for the reaction is selected from protonic acids and Lewis acids.
  • the protic acid include sulfuric acid, nitric acid, chlorosulfonic acid, p-toluenesulfonic acid, and hydrogen halide.
  • Lewis acids include metal or metalloid halides.
  • metal or metalloid halides For example, Be, B, Al, Si, P, S, Ti, V, Fe, Zn, Ga, As, Se, Zr, Nb, Mo, Cd, Sn, Sb, Te, Ta, W, hg, B i, elements such as U or PO, S eO, 'S_ ⁇ , S0 2, VO although such as oxygen one element conjugate halide or organic halide or these complexes, such as, and a carboxyl group Those which form a coordination bond with an organic compound having an aldehyde group are preferred.
  • a protonic acid More specifically BF 3, (CH 3) 2 BF, BC 1 3, A 1 C 1 3, A 1 B r 3, (C 2 H 5) A 1 C 1 2, POC 1 3, T i C 1 VC 1 4, Mo C 1 6, S n C 1 4, (CH 3) S n C 1 3, S b C 1 5, T e C 1 4 and WC 1 6 like c
  • a protonic acid Alternatively, two or more Lewis acids may be used in combination, or both acids may be used in combination.
  • the amount of these catalysts to be used is usually 0.01 to 5 mol per 1 mol of the organic compound having the group.
  • the reaction between the compound having an unsaturated bond and the organic compound having the group is usually performed in the presence of a solvent.
  • a solvent those which are inert to the catalyst and dissolve both compounds are particularly suitable.
  • aromatic solvents such as benzene and toluene
  • aliphatic solvents such as butane and hexane
  • halogenated hydrocarbon solvents such as chloroform and dichloroethane are exemplified.
  • the reaction is usually performed at a temperature of 0 to 100 ° C., for a reaction time of 10 seconds to several tens hours.
  • By adding a large amount of alcohol or hot water to the reaction system it is possible to simultaneously stop the reaction and coagulate the reaction product. If necessary, remove the remaining catalyst by washing.
  • the modified polymer (a) used in the present invention is obtained.
  • the polymer (mouth) obtained by force-pulling the anion living polymer used in the present invention with a tin compound can be produced by a known method described in JP-B-44-4996.
  • Anion polymerization is usually carried out using an alkali metal compound, especially an organolithium compound as a catalyst, but an alkaline earth metal compound can also be used.
  • Examples of the organic lithium compound include methyllithium, ethyllithium, butyllithium, octyllithium, 1,4-dilithiobutane, 1,5-dilithiopentane, and 1,10-dilithiodecane.
  • Examples of the alkaline earth metal compound catalyst include, for example, JP-A-51-115590, JP-A-52-9090, 30543, 48910, 98
  • Examples of the catalyst system include compounds such as barium, strontium, and calcium disclosed in JP-A No. 077, JP-A-56-112916, JP-A-118403, and JP-A-57-100146.
  • the amount of these anion polymerization catalysts used is determined in relation to the molecular weight of the produced polymer. Usually, it is about 0.1 to 200 millimol per 100 grams of monomer.
  • the monomers constituting the polymer are completely controlled as long as they can be anionically polymerized. Not limited.
  • conjugated diene monomers such as 1,3-butadiene, isoprene, 2,3-dimethylbutadiene, 1,3-pentene, styrene, 1-vinylnaphthalene, 1-methylstyrene, 2-vinylnaphthalene, 3—
  • monovinyl aromatic compounds such as methylstyrene
  • esters of (meth) acrylic acid such as methyl acrylate, ethyl acrylate, butyl acrylate, and methyl methacrylate.
  • the polymerization is usually carried out in a temperature range of from 120 ° C to 150 ° C.
  • the polymerization solvent include aliphatic hydrocarbon solvents such as butane, pentane, hexane, heptane, and octane; aromatic hydrocarbon solvents such as benzene, xylene, and toluene; and alicyclic solvents such as cyclohexane and methylcyclopentane.
  • aliphatic hydrocarbon solvents such as butane, pentane, hexane, heptane, and octane
  • aromatic hydrocarbon solvents such as benzene, xylene, and toluene
  • alicyclic solvents such as cyclohexane and methylcyclopentane.
  • hydrocarbon solvents One or more selected from hydrocarbon solvents are used.
  • the coupling with the tin compound can be performed during the polymerization, but is usually performed after the polymerization is completed.
  • the tin compounds used for coupling are methyltrichlorotin, dimethyldichlorotin, tetrachlorotin, dichlorotin, ethyltriclotin, tin, getyldichlorotin, tetrafluoros, methyltribromotin, dimethyldibutin, tin, phenyltrichlorotin, and phenyltrichlorotin.
  • Tin halides such as tin, 1,2 bis (trichlorostannyl) ethane, 1,4 bis (methyldichlorostannyl) butane, getyldiaryltin, propyltriaryltin, dibutyldimethoxytin, dibutylbis (octyloxy) tin, Tetramethylthiotin, tetradodeci
  • non-tin compounds such as luthiotin, dimethyltin oxide and dimethyltin sulfide, and tin halide compounds, and tin halide compounds are usually used.
  • the force coupling reaction is carried out at a temperature of 0 to 150 ° C for a period of 0.5 minutes to 20 hours.
  • the amount of the tin compound used is, for example, 1 to 1.5 equivalents of a halogen atom of an organolithium compound per equivalent of a lithium atom of the organolithium compound, taking a tin halide compound as an example.
  • the force coupling reaction is carried out in an atmosphere of an inert gas by adding a halide to the solution of the living polymer after completion of the polymerization.
  • the tin-coupling polymer is recovered from the reaction solution by using a usual polymer recovery method such as steam stripping.
  • a polymer (mouth) obtained by coupling the anion living polymer with the tin compound is obtained.
  • the polymer (c) is obtained by adding tin tetrachloride to a solution of an isoprene-based polymer in a solvent inert to tin tetrachloride, and treating the mixture with stirring.
  • isoprene-based polymers include natural rubber, polyisoprene, isoprene-butadiene copolymer (including random and block copolymers), isoprene-styrene copolymer [random copolymer and block copolymer (SI, SIS, Isoprene-acrylonitrile copolymer, isoprene-butadiene-acrylonitrile copolymer, and partially hydrides of these conjugated gen units. This In these copolymers
  • isoprene forms two or more chains.
  • Any solvent can be used as long as it dissolves the polymer and is inert to tin tetrachloride, and is not particularly limited.
  • examples thereof include aromatic hydrocarbon solvents such as benzene and toluene, alicyclic hydrocarbon solvents such as cyclohexane, and halogenated hydrocarbon solvents such as dichloromethane and ethylene dichloride. Alcohols, ketones and ethers which have chemical conversion to tin tetrachloride can also be used if the amount used is limited.
  • the concentration of the polymer in the solution is usually in the range of 1 to 50% by weight.
  • the water content in the solution is desirably 4 O O Ppm or less.
  • the amount of tin tetrachloride used varies depending on the type of solvent, water content and the like, but is usually in the range of 0.05 to 5 parts by weight per 100 parts by weight of the polymer. Reducing the amount of tin tetrachloride by coexisting an appropriate amount of a compound having active hydrogen such as trichloroacetic acid, tribromoacetic acid, water or methanol, or a halogen compound such as t-butyl chloride or benzyl chloride. Is possible.
  • a compound having active hydrogen such as trichloroacetic acid, tribromoacetic acid, water or methanol, or a halogen compound such as t-butyl chloride or benzyl chloride.
  • the processing is usually performed at 120 to 100 ° C, preferably 0 to 60 ° C. C
  • the processing time is about 1 minute to 10 hours. It is desirable to perform the treatment so that the glass transition temperature of the isoprene-based polymer after the treatment is increased by 3 ° C or less.
  • the reaction can be stopped and the reaction product can be separated at the same time by adding a large amount of alcohol or hot water to the reaction mixture or by steam stripping.
  • an isoprene-based polymer (c) treated with tin tetrachloride is obtained.
  • the particulate matter targeted by the present invention is not particularly limited, and the C-particle system which is an inorganic or organic substance having a granular form, a flake form, or a fibrous form is not particularly limited. as preferably 0 0 1 to 5 c inorganic fine particles is 0 m, for example, metal whiskers as reinforcing agents, Kure one, carbon black, silica, glass fibers, carbon fibers, carbide Geiso fiber ⁇ ;.
  • Calcium carbonate barium sulfate, mica, zinc oxide, magnesium oxide, antimony oxide, barium ferrite, strontium fluoride, aluminum hydroxide, magnesium hydroxide, basic magnesium carbonate, dolomite, dosonite, calcium sulfate, talc , Calcium gayate, pumice, montmoronite, bentonite, glass bal
  • shirasu balloon glass powder, barium titanate, tin oxide, zinc borate, zirconium titanate, etc .; titanium dioxide as pigment, iron oxide (including bengara), carbon black, zinc chromate, etc .; reactivity
  • the material include metal compounds such as zinc, magnesium, lead, and aluminum.
  • organic fine particles examples include low-molecular-weight organic compounds such as anthracene, pyrene, and fluorene; petroleum such as pitch; oil residue from naphtha under normal pressure; and asphalten; azo pigments, mordant dye lakes, phthalocyanine pigments, Pigments such as fluorescent pigments; fine particles of resins such as benzoguanamine resin, methacrylic acid resin, silicone resin, polyamide resin, polyester resin, polyphenylene xide, and fuynol-based thermosetting resin; aramid fiber, polyester fiber, polyamide fiber Single fiber chops of fibers such as 0
  • the medium in the present invention is not particularly limited as long as the above-mentioned particulate matter does not dissolve or is hardly compatible, and includes liquid and solid media c, for example, water, tetrahydrofuran, Various solvents such as acetonitrile, benzene, toluene, xylene, hexane, methyl ethyl
  • Styrene-based polymers such as polystyrene, impact-resistant polystyrene resin, ABS resin, and AS resin; polyethylene polymers, polypropylene, polyisobutylene, and other olefin-based polymers; gen-based rubber [natural rubber, polyisoprene, polybutadiene, styrene-butadiene copolymer (Including random and block), styrene-isoprene copolymer (same as left), etc.] And partially hydrides thereof, engineering plastics such as polyethylene terephthalate, polycarbonate, polysulfone ether, and polyamides, celluloses such as cell acetate, acetate, and nitrocellulose, phenolic resins, epoxy resins, unsaturated polyester resins, polyurethane resins, and silicon. curable resin such as a resin, petroleum resin, terpene resin, synthetic resins such as polybutene, but not limited to c
  • the amount of the dispersant of the present invention varies depending on the type of the medium for dispersing the inorganic and / or organic fine particles, the surface area per weight of the substance or the type of the dispersant, the molecular weight, and the like.
  • the amount is at least 0.05 part by weight, preferably 0.05 to 100 parts by weight, more preferably 3 to 50 parts by weight, per 100 parts by weight of the substance.
  • Examples of the method of using the dispersant include the following methods.
  • the dispersant and the particulate matter are stirred and mixed at a temperature of 50 to 300 ° C, and the surface of the substance is treated with the dispersant, and then added to a medium, and if necessary, stirred and mixed. how to.
  • the amount of surface treatment (adhesion) of the dispersant to the substance the amount of the dispersant
  • it is at least 1% by weight, preferably 3% by weight or more based on the weight of the substance.
  • the method of surface treatment of the particulate matter with a dispersant is not particularly limited.
  • Examples thereof include the method of dry blending of the above (3), the method of immersing the substance in a solution of a dispersant of an inert organic solvent, the method of A method of spraying and applying a suspension of a dispersant using an inert solvent such as water to the substance may be used.
  • dispersant of the present invention In order to produce a dispersion in which the substance is uniformly dispersed in a polymer using the dispersant of the present invention or the particulate substance surface-treated with the dispersant, it is necessary to sufficiently mix the polymer and the substance. is necessary. Preferred mixing conditions depend on the type of polymer, chemical structure, and the like.
  • the dispersant and the substance are surface-treated with a dispersant using a conventional mixer such as a Henschel mixer, a Hobart mixer, a Banbury mixer, or a twin-screw extruder, and then mixed with the polymer. You may.
  • Processing of the polymer is generally performed at a temperature well above the glass transition temperature of the polymer, preferably at a temperature at which the polymer has a low melt viscosity.
  • the temperatures at which good processing takes place are, for example, in the temperature range of 170-230 ° C for low-density polyethylene, in the temperature range of 200-250 ° C for high-density polyethylene, and for polystyrene.
  • the temperature conditions for mixing the polymer and the particulate matter other than those exemplified in c may be a temperature range known to those skilled in the art for the target polymer.
  • a commonly used mixer can be used and is not particularly limited.
  • two-roll mill, c which include Wari ring blender Chancellor
  • Wari ring blender Chancellor When manufacturing by dissolving or dispersing various substances in a liquid medium (at room temperature or when heated) such as paints and inks, it is difficult to disperse them evenly.
  • a dispersion in which an agent, various pigments (for example, described in Kiki Color Index, Third Edition) and the like are dispersed in a suitable solvent such as water or an organic solvent.
  • a suitable solvent such as water or an organic solvent.
  • the substance and the amount suitable for the purpose may be selected.
  • the substance and the amount used are not particularly limited. Uses include carbon black, inorganic pigments, organic pigments and dyes, and toner (using a toner for electrostatic copying as a dispersion).
  • the medium of the dispersion composition is also selected according to the use of the dispersion composition, and is not particularly limited in the present invention.
  • a method of dispersing the particulate matter in a liquid medium for example, a solvent
  • a method in which the substance is added to a solvent to which a necessary amount of a dispersant is added a method in which the necessary amount of a dispersant and the substance are added to the solvent, Or a method in which the substance previously surface-treated with a dispersant is added to a solvent as described above, but other methods may be used.
  • the dispersant of the present invention can be used in various media of various inorganic and organic fine particles. It has a function of stabilizing the dispersion, which makes it easy to uniformly disperse the particles and prevents reaggregation. Further, since the increase in the viscosity of the system to which the substance is added is suppressed, the processability and transportability of the dispersion or the filling property of the substance are improved. C.
  • the thermal transfer ink contains at least one of the above-mentioned dispersant polymers (a) to (c), carbon black and a binder as main components, and the polymers (a) to (c) contain carbon black as the binder. It works to disperse it evenly, and as a result, the image obtained by using this thermal transfer ink becomes high quality and excellent in durability.
  • a binder conventionally used for this purpose is used. Examples of the above-mentioned waxes, higher fatty acids and various polymers of metal salts thereof, and the like. Carbon blacks conventionally used for this purpose are also used. Carbon black is usually used in the ink in the range of 5 to 40% by weight. If desired, other additives can be used.
  • the thermal transfer ink is produced by melt-kneading a binder and carbon black and, if necessary, other additives in the presence of the dispersant of the present invention. Due to the presence of the dispersant, it is extremely easy to disperse the carbon black into the binder.It is only necessary to mix with low shear using a stirrer such as a conventional stirrer with various shapes and a static mixer. It is enough. If a polymer having a monomer composition and a molecular weight suitable for the binder is selected as the dispersant of the present invention, the dispersant of the present invention can be used without adding another binder.
  • the prepared thermal transfer ink is represented by polyethylene terephthalate film, polyimide film, condenser paper, silk fabric, aluminum foil, etc. It can be applied to the support by a conventionally used method such as hot melt coating, reverse roll coating, and gravure opening coating, so that a thermal transfer sheet of excellent quality can be obtained. it can
  • thermal transfer ink using the dispersant of the present invention is uniformly dispersed in the carbon black binder component, an image recorded using this ink is compared with an image using the conventional thermal transfer ink. The quality is remarkably high and the image durability is excellent.
  • M n is the number average molecular weight in terms of standard polystyrene measured by GPC.
  • the amount of the dispersant added is% by weight with respect to the inorganic fine particles.
  • a vulcanized compound of polyisoprene rubber (Nip012200, manufactured by Nippon Zeon Co., Ltd.) was prepared, and the vulcanization properties were improved by improving the dispersibility of carbon black.
  • the rubber was first mixed with carbon black using a small Banbury mixer, and sulfur and a vulcanization accelerator were added to the mixture using a small roll and mixed.
  • This compound was press-vulcanized at 140 ° C for 25 minutes to obtain a vulcanized product, and the strength characteristics and rebound resilience (using a Dunlop trypsometer at room temperature) were measured. The results are shown in Table 4. c
  • Dispersant ⁇ or ⁇ Add 10 parts of azo organic pigment lake C (manufactured by Dainichi Seika) and 20 parts to 200 parts of toluene / methylethyltoluene (1/1) Then, after irradiating with ultrasonic waves (same as in Example 1) for 1 minute, the mixture was stirred under the condition of 300 rpm to prepare a dispersion liquid (dispersion composition) of the organic pigment.
  • azo organic pigment lake C manufactured by Dainichi Seika
  • the dispersibility of this dispersion was evaluated by the amount of the organic pigment remaining on the filter after passing through a N03 glass filter, and the dispersion stability was evaluated from the sedimentation state of the organic pigment over time of the dispersion passed through the filter.
  • the dispersibility was indicated by “ ⁇ ” when excellent without residual amount, and “X” when the residual amount was inferior.
  • Dispersion stability was indicated by ⁇ when it was excellent without sedimentation even after one month, and X when it settled and was inferior after one week. The results are shown in Table 5.
  • the mixture was stirred and mixed at 100 ° C for 30 minutes to prepare a thermal transfer ink.
  • Each of the obtained inks was thinly applied on a glass plate, and the dispersibility of carbon black was observed with an optical microscope. Good or bad dispersibility was indicated by ⁇ and X.
  • Each ink was coated on a 6 ⁇ m-thick biaxially stretched polyethylene terephthalate (PET) film so that the dry thickness of the ink was 5 // m. It was applied using.
  • PET polyethylene terephthalate
  • the inks were heated so that each of them was in an optimal flow state.
  • the resulting thermal transfer sheet was mounted on a thermal printer and printed on plain paper. The quality of the print was evaluated on a 5-point scale, including the resolution and the presence or absence of white spots.
  • the raw materials for dispersants A, D and J were used as dispersants A ', D' and J ', respectively, and these were used to prepare and evaluate a thermal transfer ink in the same manner in accordance with the formulation shown in Table 6. Furthermore, a thermal transfer ink (Nol 7) without using a dispersant was prepared and evaluated. The results are shown in Table 6.
  • the dispersant of the present invention can be used in the manufacture of a wide range of products that require uniform dispersion of various particulate substances.
  • bonded magnets using magnetic materials variant magnetic powders
  • magnetic recording media toner for electrostatic image development, discs, tapes (magnetic powder in magnetic recording layer and back coat layer, binder such as carbon black)
  • Paints and molded articles using EMI materials inks using pigments (printing inks, thermal transfer inks, conductive inks, etc.); thermal transfer ink ribbon coating agents: paints, conductive materials, etc.
  • Conductive and electrostatic composite materials used Wires, building materials, etc. using arrogant materials; Dyes, catalysts, etc.
  • dispersion and stabilizing materials Fillers, reinforcing agents, antifriction materials, etc. Rubber and plastic molded products, FRP, FRTP, etc .; used to manufacture various oils (for example, lubricating oils, engine oils, etc.) to which oil additives such as sludge dispersants, detergent dispersants, and load additives are added. be able to.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (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)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

L'invention se rapporte à un dispersant qui est utilisé pour disperser des particules fines dans un milieu et qui contient au moins un polymère choisi parmi un polymère modifié obtenu grâce à la réaction d'un polymère insaturé avec un composé organique renfermant des groupes à la fois carboxyle et aldéhyde en présence d'un acide protonique ou d'un acide de Lewis, un polymère obtenu par couplage de polymères vifs anioniques par l'intermédiaire d'un composé d'étain, et un polymère d'isoprène traité au moyen de trétrachlorure d'étain. Ce dispersant peut être utilisé dans la fabrication d'une grande variété de produits, dans lesquels une dispersion homogène de diverses substances particulaires est requise, par exemple pour des supports d'entregistrement magnétique, des encres à thermotransfert, des matériaux d'enduction, des substances toner pour le développement d'images à charge électrostatique, etc.
PCT/JP1991/001131 1990-08-28 1991-08-27 Dispersant, substance particulaire traitee en surface, procede d'utilisation de dispersant et compositon de dispersion Ceased WO1992003222A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP2224503A JPH04108873A (ja) 1990-08-28 1990-08-28 感熱転写インキ
JP2224502A JPH04108874A (ja) 1990-08-28 1990-08-28 分散剤、表面処理された微粒子状物質、分散剤の使用方法並びに分散液
JP2/224503 1990-08-28
JP2/224502 1990-08-28

Publications (1)

Publication Number Publication Date
WO1992003222A1 true WO1992003222A1 (fr) 1992-03-05

Family

ID=26526097

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP1991/001131 Ceased WO1992003222A1 (fr) 1990-08-28 1991-08-27 Dispersant, substance particulaire traitee en surface, procede d'utilisation de dispersant et compositon de dispersion

Country Status (1)

Country Link
WO (1) WO1992003222A1 (fr)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS50111138A (fr) * 1973-12-29 1975-09-01
JPS62164766A (ja) * 1986-01-14 1987-07-21 Nippon Soda Co Ltd 表面処理剤
JPH0252032A (ja) * 1988-08-12 1990-02-21 Japan Synthetic Rubber Co Ltd 固形燃料スラリー組成物
JPH02113008A (ja) * 1988-10-21 1990-04-25 Kuraray Co Ltd 片末端に非置換もしくは置換ビニル基を有する共役ジエン系マクロモノマー、及びその製造方法及びそれを含有する組成物

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS50111138A (fr) * 1973-12-29 1975-09-01
JPS62164766A (ja) * 1986-01-14 1987-07-21 Nippon Soda Co Ltd 表面処理剤
JPH0252032A (ja) * 1988-08-12 1990-02-21 Japan Synthetic Rubber Co Ltd 固形燃料スラリー組成物
JPH02113008A (ja) * 1988-10-21 1990-04-25 Kuraray Co Ltd 片末端に非置換もしくは置換ビニル基を有する共役ジエン系マクロモノマー、及びその製造方法及びそれを含有する組成物

Similar Documents

Publication Publication Date Title
US4994520A (en) Carbon black-graft polymer, method for production thereof, and use thereof
JP3098033B2 (ja) 封入磁性粒子，顔料及びカーボンブラック，それに関連した組成物及び方法
EP0978766B1 (fr) Toner pour developpement d'image electrostatique, contenant de la resine a base de polyolefine a structure cyclique
US6001533A (en) Composition for forming non-conductive light-shielding layer, and non-conductive light-shielding layer containing same
WO1988003545A1 (fr) Fines particules spheriques colorees, procede de production et utilisations
EP1377614A2 (fr) Polymeres, copolymeres et derives de polypropylene isotactiques de faible poids moleculaire et substances preparees au moyen de ceux-ci
CA3117242A1 (fr) Composition d'appret conductrice et son procede de preparation
US5482809A (en) Liquid toners from soluble polymeric dispersants with reactive groups
US5272212A (en) Colored spherical fine particles, process for production thereof and applications thereof
EP1669408B1 (fr) Composition de composite spherique et procede de production d'une composition de composite spherique
US5294233A (en) Additive for organic medium or thermoplastic polymer
WO1992003222A1 (fr) Dispersant, substance particulaire traitee en surface, procede d'utilisation de dispersant et compositon de dispersion
JP4781534B2 (ja) エポキシ系液体トナー配合物
JPH0625869B2 (ja) 磁性トナ−の製造法
JPH04108874A (ja) 分散剤、表面処理された微粒子状物質、分散剤の使用方法並びに分散液
JPS5891702A (ja) ゴム状重合体の回収方法
JP2001272816A (ja) 静電荷像現像用トナー
US5780167A (en) Magnetic recording medium having a binder comprising a star block polymer with dispersing groups
JP3083306B2 (ja) 分散剤、表面処理された無機物質及び有機微粒子並びに分散剤の使用方法
JP3259005B2 (ja) 分散剤、表面処理された微粒子及び分散剤の使用方法
JP2891634B2 (ja) ポリマーマイクロカプセルの製造方法
JPH04108873A (ja) 感熱転写インキ
JP2007238415A (ja) ポリマー被覆炭素質材料、ポリマー被覆炭素質材料の製造方法及びトナー
JPS5817551B2 (ja) 塗料用組成物
JPH0657006A (ja) 非水溶媒中でのポリマー微粒子の製法

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): DE GB KR US

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AT BE CH DE DK ES FR GB GR IT LU NL SE

REG Reference to national code

Ref country code: DE

Ref legal event code: 8642