WO2023136228A1 - 無機粒子分散用ビヒクル組成物、無機粒子分散用ビヒクル組成物の製造方法、無機粒子分散スラリー組成物、及び、電子部品の製造方法 - Google Patents

無機粒子分散用ビヒクル組成物、無機粒子分散用ビヒクル組成物の製造方法、無機粒子分散スラリー組成物、及び、電子部品の製造方法 Download PDF

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WO2023136228A1
WO2023136228A1 PCT/JP2023/000245 JP2023000245W WO2023136228A1 WO 2023136228 A1 WO2023136228 A1 WO 2023136228A1 JP 2023000245 W JP2023000245 W JP 2023000245W WO 2023136228 A1 WO2023136228 A1 WO 2023136228A1
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weight
meth
inorganic particle
inorganic particles
composition
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PCT/JP2023/000245
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French (fr)
Japanese (ja)
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健司 山内
丈 大塚
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積水化学工業株式会社
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    • 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
    • C08F20/00—Homopolymers and 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
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/10—Esters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/01—Hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or 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 of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/04—Homopolymers or copolymers of esters
    • C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical

Definitions

  • the present invention relates to a vehicle composition for dispersing inorganic particles, a method for producing a vehicle composition for dispersing inorganic particles, a slurry composition for dispersing inorganic particles, and a method for producing an electronic component.
  • compositions in which inorganic particles such as ceramic powders and glass particles are dispersed in a binder resin have been used in the production of multilayer electronic components such as multilayer ceramic capacitors.
  • Such laminated ceramic capacitors are generally manufactured using the following method. First, after adding additives such as a plasticizer and a dispersant to a solution of a binder resin dissolved in an organic solvent, ceramic raw material powder is added and mixed uniformly using a ball mill or the like to obtain an inorganic particle dispersion composition. .
  • the resulting inorganic particle dispersion composition is cast on the surface of a support such as a release-treated polyethylene terephthalate film or SUS plate using a doctor blade, reverse roll coater, or the like, and volatile matter such as an organic solvent is collected. After removing it, it is peeled off from the support to obtain a ceramic green sheet. Next, the resulting ceramic green sheets are coated with a conductive paste that will become internal electrodes by screen printing or the like, and a plurality of these sheets are stacked, heated and pressure-bonded to obtain a laminate.
  • the resulting laminate is heated to thermally decompose and remove components such as the binder resin, ie, a so-called degreasing treatment, followed by firing to obtain a fired ceramic body having internal electrodes. Further, external electrodes are applied to the end faces of the fired ceramic body obtained, and fired to complete a laminated ceramic capacitor.
  • the firing process often causes problems such as swelling and cracking of the fired body, and it is desirable to degrease the binder resin at a low temperature in a short period of time. Therefore, the use of a binder resin that can be fired at a low temperature and has a low residual carbon component after firing has been studied.
  • Patent Document 1 discusses the use of paraffin wax or polyethylene glycol in order to keep the degreasing temperature at a relatively low temperature of 230°C to 350°C.
  • Patent Document 2 an acrylic resin having an average molecular weight of 2.0 ⁇ 10 5 or more, an acid value of 2.4 to 7.2, and a glass transition temperature of 50 to 90° C. is used as the binder resin. It is considered to enhance the removability of
  • the present disclosure (1) is a composition containing a (meth) acrylic resin, a terpene compound, and a solvent, wherein the terpene compound has a boiling point of 150 ° C. or higher and 320 ° C. or lower, and a double bond in the molecule and containing 0.02 parts by weight or more and 1.8 parts by weight or less of the terpene compound relative to 100 parts by weight of the (meth)acrylic resin, a vehicle composition for dispersing inorganic particles.
  • the present disclosure (2) is the vehicle composition for dispersing inorganic particles of the present disclosure (1), wherein the terpene compound is at least one selected from the group consisting of monoterpene compounds and sesquiterpene compounds.
  • the terpene compound is geraniol, linalool, myrcene, limonene, nerol, ⁇ -ocimene, ⁇ -ocimene, ⁇ -terpinene, terpinolene, phellandrene, amorphadiene, ⁇ -farnesene, ⁇ -farnesene, farnesol , nerolidol, carvone, geranic acid, citral and citronellal, the vehicle composition for dispersing inorganic particles of the present disclosure (1) or (2).
  • the present disclosure (4) is an inorganic particle dispersion in any combination with any of the present disclosure (1) to (3), wherein the solvent is at least one selected from the group consisting of terpineol, dihydroterpineol and dihydroterpineol acetate It is a vehicle composition for The present disclosure (5) is a vehicle for dispersing inorganic particles in any combination with any of the present disclosures (1) to (4), wherein the (meth)acrylic resin contains 40% by weight or more of a segment derived from isobutyl methacrylate. composition.
  • a (meth)acrylic resin is produced by adding a polymerization initiator to a raw material monomer mixture containing a (meth)acrylic acid ester and a raw material monomer mixture containing a solvent to copolymerize the raw material monomer mixture.
  • the polymerization initiator is an organic peroxide, and the amount of active oxygen in the polymerization initiator is 0.04 parts by weight or more with respect to 100 parts by weight of the raw material monomer mixture in the presence of the terpene compound.
  • the present disclosure (7) is a vehicle composition for dispersing inorganic particles according to any one of the present disclosures (1) to (5), and an inorganic particle-dispersed slurry composition containing inorganic particles.
  • the present disclosure (8) is a method for producing an electronic component, comprising a step of degreasing at a temperature of 300° C. or higher and 400° C. or lower using the inorganic particle-dispersed slurry composition of the present disclosure (7).
  • the present invention will be described in detail below.
  • the reason why the degreasing time of the (meth)acrylic resin is long is that the thermal decomposition of the (meth)acrylic resin progresses through the following mechanism.
  • the firing environment temperature is higher than the ceiling temperature of (meth)acrylic resin.
  • a depolymerization reaction occurs in which a portion of the decomposed monomer is further thermally oxidatively combusted and decomposed into lower molecular weight components.
  • most of the decomposed monomers are repolymerized into polymers by the heat of baking.
  • most of the thermally decomposed polymer components are polymerized again, so the apparent decomposition rate for decomposing the (meth)acrylic resin is slow, which causes degreasing to take a long time. .
  • the present inventors have found that by adding a predetermined amount of a specific terpene compound to a (meth)acrylic resin, it is possible to suppress the repolymerization of decomposed monomers in the degreasing process and increase the decomposition initiation temperature. It has been found that the apparent decomposition rate can be improved and degreasing can be performed at a low temperature for a short period of time. In addition, they have found that a vehicle composition for dispersing inorganic particles containing such a specific terpene compound is also excellent in viscosity stability.
  • the vehicle composition for dispersing inorganic particles contains a (meth)acrylic resin.
  • the (meth)acrylic resin is not particularly limited, it preferably contains a segment derived from a (meth)acrylic acid ester having an ester substituent having 8 or less carbon atoms.
  • that the number of carbon atoms in the ester substituent is 8 or less means that the total number of carbon atoms other than the carbon atoms constituting the (meth)acryloyl group in the (meth)acrylic acid ester is 8 or less.
  • the (meth)acrylic acid ester having an ester substituent having 8 or less carbon atoms means anything other than the (meth)acrylic acid ester having a glycidyl group, which will be described later.
  • Examples of (meth)acrylic acid esters having an ester substituent having 8 or less carbon atoms include (meth)acrylic acid esters having a linear, branched or cyclic alkyl group.
  • Examples of the (meth)acrylic acid ester having a linear alkyl group include methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, n-butyl (meth)acrylate and the like.
  • Examples of the (meth)acrylic acid ester having a branched alkyl group include alkyl such as t-butyl (meth)acrylate, isobutyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, and benzyl (meth)acrylate. (Meth)acrylates are mentioned.
  • Examples of the (meth)acrylic ester having a cyclic alkyl group include cyclohexyl (meth)acrylate.
  • the (meth)acrylic acid esters in which the ester substituent has 8 or less carbon atoms include 2-hydroxyethyl (meth)acrylate, hydroxypropyl (meth)acrylate, hydroxybutyl (meth)acrylate, (meth)acryl A (meth)acrylic acid ester having a hydroxyl group or a carboxyl group such as an acid can also be used. Among them, since it can be quickly degreased at low temperature, it is possible to have a segment derived from a (meth)acrylic acid ester having a linear alkyl group or a (meth)acrylic acid ester having a branched alkyl group.
  • the (meth)acrylic acid ester having a carbon number of 8 or less in the ester substituent includes a (meth)acrylic acid ester having a linear alkyl group and a (meth)acrylic acid ester having a branched alkyl group. Combinations of acid esters are preferred.
  • (meth) acrylic acid ester having 8 or less carbon atoms in the ester substituent a (meth) acrylic acid ester having 1 to 4 carbon atoms in the ester substituent may be used.
  • (Meth)acrylic acid esters having a number of 5 to 8 may be used.
  • the content of the segment derived from the (meth)acrylic acid ester having 8 or less carbon atoms in the ester substituent in the (meth)acrylic resin is 40% by weight or more because it can improve low-temperature decomposability and stringiness. is preferably 50% by weight or more, more preferably 55% by weight or more, even more preferably 60% by weight or more, preferably 100% by weight or less, more preferably 95% by weight or less, and even more preferably 80% by weight or less . Within the above range, the low-temperature decomposability of the binder resin can be improved, and excellent toughness can be imparted to the resulting ceramic green sheet.
  • the content of the segment derived from the (meth)acrylic acid ester having 1 to 4 carbon atoms in the ester substituent in the (meth)acrylic resin is preferably 30% by weight or more, and 35% by weight from the viewpoint of low-temperature decomposability. It is more preferably 100% by weight or less, more preferably 95% by weight or less, even more preferably 90% by weight or less, even more preferably 84% by weight or less, and particularly preferably 82% by weight or less.
  • the content of the segment derived from the (meth)acrylic acid ester having 1 to 2 carbon atoms in the ester substituent in the (meth)acrylic resin is preferably 10% by weight or more from the viewpoint of low-temperature decomposability, and 20 % by weight or more is more preferable, 40% by weight or less is preferable, and 30% by weight or less is more preferable.
  • the content of the segment derived from the (meth)acrylic acid ester having 3 to 4 carbon atoms in the ester substituent in the (meth)acrylic resin is preferably 40% by weight or more from the viewpoint of low-temperature decomposability, and 50 It is more preferably 90% by weight or less, and more preferably 80% by weight or less.
  • the content of the segment derived from the (meth)acrylic ester having 5 to 8 carbon atoms in the ester substituent in the (meth)acrylic resin is preferably 0% by weight or more from the viewpoint of low-temperature decomposability. It is more preferably 15% by weight or more, still more preferably 18% by weight or more, preferably 50% by weight or less, more preferably 40% by weight or less, and even more preferably 30% by weight or less.
  • the content of the segment derived from the isobutyl methacrylate in the (meth)acrylic resin is preferably 40% by weight or more, more preferably 50% by weight or more, preferably 70% by weight or less, and 60% by weight from the viewpoint of low-temperature decomposability. % or less is more preferable.
  • the (meth)acrylic resin may have a segment derived from a (meth)acrylic acid ester having an ester substituent having 9 or more carbon atoms.
  • a segment derived from a (meth)acrylic ester having 9 or more carbon atoms in the ester substituent By having a segment derived from a (meth)acrylic ester having 9 or more carbon atoms in the ester substituent, the decomposition end temperature of the (meth)acrylic resin can be sufficiently lowered, and the obtained inorganic particles Dispersion sheets can be toughened.
  • the ester substituent preferably has a branched chain structure from the viewpoint of low-temperature decomposability.
  • the number of carbon atoms in the ester substituent is preferably 30 or less, more preferably 20 or less, even more preferably 10 or less.
  • Examples of the (meth)acrylic acid ester having an ester substituent having 9 or more carbon atoms include a (meth)acrylic acid ester having a linear or branched alkyl group having 9 or more carbon atoms, polyalkylene glycol (Meth)acrylate and the like.
  • Examples of the (meth)acrylic acid ester having a linear or branched alkyl group include n-nonyl (meth)acrylate, isononyl (meth)acrylate, n-decyl (meth)acrylate, isodecyl (meth) Acrylate, n-lauryl (meth)acrylate, isolauryl (meth)acrylate, n-stearyl (meth)acrylate, isostearyl (meth)acrylate and the like.
  • (meth)acrylic acid esters having a branched alkyl group having 9 or more carbon atoms are preferable, and isononyl (meth)acrylate, isodecyl (meth)acrylate, and isostearyl (meth)acrylate are more preferable.
  • the above isodecyl methacrylate is particularly excellent in decomposability as compared with other long-chain alkyl methacrylates.
  • polyalkylene glycol (meth)acrylate examples include those having ethylene glycol units (oxyethylene units), propylene glycol units (oxypropylene units), butylene glycol units (oxybutylene units), and the like.
  • the above polyalkylene glycol (meth)acrylate may have an alkoxy group at its terminal, or may have an ethylhexyl group at its terminal.
  • the alkoxy group examples include a methoxy group, an ethoxy group, and a butoxy group.
  • the alkoxy group may be linear or branched, preferably branched.
  • the polyalkylene glycol (meth)acrylate preferably has a branched alkylene glycol structure.
  • polyalkylene glycol (meth)acrylates having at least one of ethylene glycol units, propylene glycol units, and butylene glycol units are preferred. More preferred are polyethylene glycol methacrylate, polypropylene glycol methacrylate, ethoxypolypropylene glycol methacrylate, methoxypolypropylene glycol methacrylate, polybutylene glycol methacrylate, and polypropylene glycol-polybutylene glycol methacrylate.
  • Methoxypolypropylene glycol methacrylate, polypropylene glycol methacrylate, polybutylene glycol methacrylate, and propylene glycol-polybutylene glycol methacrylate have less baking residue and are particularly excellent in low-temperature decomposability compared to other alkylene glycol (meth)acrylates.
  • the content of the segment derived from the (meth)acrylic acid ester having 9 or more carbon atoms in the ester substituent in the (meth)acrylic resin is preferably 5% by weight or more, and 10% by weight, from the viewpoint of low-temperature decomposability. % or more, preferably 40% by weight or less, and more preferably 30% by weight or less.
  • the (meth)acrylic resin may have a segment derived from a (meth)acrylic acid ester having a glycidyl group.
  • a segment derived from the (meth)acrylic ester having a glycidyl group By having a segment derived from the (meth)acrylic ester having a glycidyl group, the strength of the obtained laminate can be sufficiently improved.
  • Examples of the (meth)acrylic acid ester having a glycidyl group include glycidyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate glycidyl ether, 3,4-epoxycyclohexylmethyl (meth)acrylate and the like.
  • the content of the segment derived from the (meth)acrylic acid ester having a glycidyl group in the (meth)acrylic resin is preferably 0% by weight or more, and preferably 1% by weight or more, from the viewpoint of solvent resistance and low-temperature decomposability. It is more preferably 2% by weight or more, preferably 10% by weight or less, and more preferably 7% by weight or less.
  • the content of the (meth)acrylic resin in the vehicle composition for dispersing inorganic particles is not particularly limited, but is preferably 5% by weight or more and preferably 80% by weight or less. By setting the content of the (meth)acrylic resin within the above range, it is possible to obtain an inorganic particle-dispersed slurry composition that can be degreased even when fired at a low temperature.
  • the content of the (meth)acrylic resin is more preferably 6% by weight or more, still more preferably 15% by weight or more, even more preferably 30% by weight or more, and more preferably 78% by weight or less.
  • the weight-average molecular weight of the (meth)acrylic resin in terms of polystyrene is preferably 10,000 or more, and preferably 200,000 or less.
  • the vehicle composition for dispersing inorganic particles has sufficient viscosity, and by setting the weight average molecular weight to 200,000 or less, printability can be improved. It becomes possible. Further, within the above range, a sufficient viscosity can be secured even with a relatively small amount of the binder resin, and an inorganic particle-dispersed slurry composition with improved stringiness can be obtained.
  • the weight average molecular weight is more preferably 30,000 or more, and more preferably 190,000 or less.
  • the ratio (Mw/Mn) of the weight average molecular weight (Mw) to the number average molecular weight (Mn) is preferably 2 or more and 8 or less.
  • the component having a low degree of polymerization is appropriately contained, so that the viscosity of the vehicle composition for dispersing inorganic particles is within a suitable range, and productivity can be enhanced.
  • the sheet strength of the obtained inorganic particle-dispersed sheet can be made moderate. Further, if the Mw/Mn is less than 2, the leveling property during coating of the green sheet may be poor, and the smoothness of the green sheet may be deteriorated.
  • Mw/Mn is more than 8, the amount of high-molecular-weight components increases, which may result in poor drying properties of the green sheet and poor surface smoothness.
  • the Mw/Mn is more preferably 3 or more, and more preferably 7 or less.
  • the weight-average molecular weight and number-average molecular weight in terms of polystyrene can be obtained by GPC measurement using, for example, a column LF-804 (manufactured by Showa Denko KK).
  • the glass transition temperature (Tg) of the (meth)acrylic resin is not particularly limited, but is preferably 30°C or higher, and preferably lower than 60°C. When the glass transition temperature is within the above range, the amount of plasticizer added can be reduced, and the low-temperature decomposability of the (meth)acrylic resin can be improved.
  • the Tg can be measured using, for example, a differential scanning calorimeter (DSC).
  • the glass transition temperature is more preferably 35° C. or higher, still more preferably 40° C. or higher, and more preferably 55° C. or lower.
  • the (meth)acrylic resin has a time required to decompose 90% by weight when heated from 30° C. to 5° C./min (hereinafter also referred to as “90% by weight decomposition time”) of 50 minutes or less. preferable. As a result, extremely high low-temperature decomposability can be achieved and the time required for degreasing can be shortened.
  • the 90% by weight decomposition time can be measured using, for example, TGDTA.
  • the method for producing the (meth)acrylic resin is not particularly limited.
  • a method comprising the steps of: adding a polymerization initiator to a starting monomer mixture containing a (meth)acrylic acid ester and a starting monomer mixture containing a solvent to copolymerize the starting monomer mixture to produce a (meth)acrylic resin.
  • a solvent or the like is added to a raw material monomer mixture containing a (meth)acrylic ester or the like to prepare a monomer mixture.
  • a method of adding a polymerization initiator to the resulting monomer mixture to copolymerize the raw material monomer mixture can be mentioned.
  • a terpene compound having two or more double bonds in the molecule may be added to the monomer mixed solution.
  • the polymerization method is not particularly limited, and examples thereof include emulsion polymerization, suspension polymerization, bulk polymerization, interfacial polymerization, and solution polymerization. Among them, solution polymerization is preferred because of its simplicity and high yield.
  • the polymerization initiator is not particularly limited, it is preferably an organic peroxide.
  • the 10-hour half-life temperature of the organic peroxide is preferably 45° C. or higher, more preferably 50° C. or higher, preferably lower than 74° C., and preferably 70° C. or lower. more preferred. By using such an organic peroxide, decomposability can be enhanced.
  • the above 10-hour half-life temperature means the temperature at which 50% of the organic peroxide decomposes in 10 hours, and is determined by the iodometric titration method, titration using a ferroin indicator, colorimetric method using ferrous salt, infrared It can be measured by spectrum or the like.
  • polymerization initiator examples include di(3,5,5-trimethylhexanoyl) peroxide (10-hour half-life temperature 59.4° C., active oxygen content 5.09%), dilauryl peroxide (10-hour half-life temperature 61.6°C, active oxygen content 4.01%), disuccinic acid peroxide (10-hour half-life temperature 65.9°C, active oxygen content 6.83%), dibenzoyl peroxide (10-hour half-life Temperature 73.6 ° C., active oxygen content 6.61%), t-butyl hydroperoxide (10-hour half-life temperature 166.5 ° C., active oxygen content 17.75%), di-t-butyl peroxide (10 time half-life temperature 123.7°C, active oxygen content 10.94%), tertiary hexyl peroxypivalate (10-hour half-life temperature 53.2°C, active oxygen content 7.91%), t-butyl peroxy Neodecanoate (10-hour half-life temperature 48 ° C., active oxygen
  • the active oxygen content (%) of the polymerization initiator can be determined by [(number of peroxide bonds in the molecule ⁇ 16)/molecular weight].
  • the amount of the polymerization initiator to be added is not particularly limited. It is preferable to adjust the amount of the polymerization initiator to be added so as to be 0.4 parts by weight or more and 0.3 parts by weight or less.
  • the amount of active oxygen with respect to 100 parts by weight of the raw material monomer mixture is more preferably 0.06 parts by weight or more, still more preferably 0.08 parts by weight or more, more preferably 0.29 parts by weight or less, and further 0.26 parts by weight or less. preferable.
  • the amount of the polymerization initiator to be added as described above the reaction rate can be improved and the amount of residual monomers can be reduced.
  • the method of adding the polymerization initiator is not particularly limited, but if a large amount is added at once, the reaction may run out of control, so it is preferable to add the polymerization initiator in multiple portions.
  • the vehicle composition for dispersing inorganic particles contains a terpene compound.
  • the terpene compound has a boiling point of 150° C. or higher and 320° C. or lower and has two or more double bonds in the molecule.
  • By containing the terpene compound it becomes possible to trap monomer radicals generated by thermal decomposition of the resin during degreasing and baking, and prevent repolymerization of the monomer. As a result, the decomposition start temperature can be lowered, and degreasing can be performed at a lower temperature in a shorter period of time.
  • the terpene compounds are terpenes and derivatives thereof. Specifically, hydrocarbons or derivatives thereof represented by (C 5 H 8 ) n composed of two or more isoprene units, monoterpene compounds, sesquiterpene compounds, diterpene compounds, sesterterpene compounds, triterpene compounds, tetraterpene compounds, and the like. 1 or more and 4 or less are preferable, and, as for n, 2 or more and 3 or less are more preferable. As the terpene compound, a monoterpene compound and a sesquiterpene compound are particularly preferable. Moreover, the terpene compound may have an acyclic structure, or may have a cyclic structure such as a monocyclic structure or a polycyclic structure. Among them, a monocyclic structure is preferred.
  • the terpene compound has two or more double bonds in the molecule, preferably two to four double bonds, more preferably two to three double bonds.
  • the boiling point of the terpene compound is 150° C. or higher, preferably 160° C. or higher, more preferably 170° C. or higher, 320° C. or lower, preferably 300° C. or lower, and more preferably 290° C. or lower.
  • the said boiling point means the boiling point in a normal pressure.
  • the boiling point can be measured, for example, by a boiling point elevation method, a dynamic method, a Siwoloboff method, or the like.
  • Science of Petroleum, Vol. II. Converted values may be used as described on page 1281 (1938).
  • terpene compounds include geraniol (boiling point 229°C), linalool (boiling point 198°C), myrcene (boiling point 167°C), limonene (boiling point 176°C), nerol (225°C), ⁇ -ocimene (boiling point 180°C), ⁇ -ocimene (boiling point 180°C), ⁇ -terpinene (boiling point 187°C), terpinolene (boiling point 185°C), amorphadiene (boiling point 240°C), ⁇ -farnesene (boiling point 240°C), ⁇ -farnesene ( boiling point 240°C), farnesol (boiling point 320°C), nerolidol (boiling point 290°C), carvone (231°C), gellanic acid (250°C), citral (
  • the content of the terpene compound in the vehicle composition for dispersing inorganic particles is 0.02 parts by weight or more and 1.8 parts by weight or less with respect to 100 parts by weight of the (meth)acrylic resin.
  • the effect of promoting thermal decomposition can be sufficiently exhibited, and organic substances are less likely to remain when used to produce ceramic green sheets, and cracking and swelling of the fired body can be prevented.
  • a highly reliable multilayer ceramic capacitor can be obtained.
  • the increase in viscosity over time can be suppressed.
  • the content is too high, the polymerization reaction will be difficult to proceed, especially when polymerizing in the presence of a terpene compound, and the polymer conversion rate may deteriorate.
  • the content of the terpene compound relative to 100 parts by weight of the acrylic resin is preferably 0.02 parts by weight or more, more preferably 0.05 parts by weight or more, preferably 1.8 parts by weight or less, and more preferably 1.2 parts by weight or less. preferable.
  • the content of the terpene compound can be measured by, for example, GC-MS.
  • the vehicle composition for dispersing inorganic particles contains a solvent.
  • the solvent is not particularly limited, it is preferable that it is excellent in coatability, drying property, dispersibility of inorganic powder, etc. when producing the inorganic particle-dispersed sheet.
  • the solvent include alcohols, ketones, acetic esters, carboxylic acid esters, aromatic hydrocarbons, terpenes and the like. In a preferred embodiment of the present invention, alcohols, ketones, acetic esters, aromatic hydrocarbons, and terpenes are more preferred as solvents.
  • the above terpenes are different from the above terpene compounds.
  • Monoethyl ether diethylene glycol monomethyl ether, diethylene glycol monoisobutyl ether, trimethylpentanediol monoisobutyrate, butyl carbitol, butyl carbitol acetate, terpineol, terpineol acetate, dihydroterpineol, dihydroterpineol acetate, texanol, isophorone, butyl lactate, dioctyl phthalate, dioctyl adipate, benzyl alcohol, phenylpropylene glycol, cresol and the like.
  • ethanol, toluene, xylene, butyl acetate, hexyl acetate, methyl ethyl ketone, terpineol, dihydroterpineol and dihydroterpineol acetate are preferable, and terpineol, dihydroterpineol and dihydroterpineol acetate are more preferable.
  • these solvents may be used independently and may use 2 or more types together.
  • the boiling point of the solvent is preferably 90°C or higher, and preferably 240°C or lower.
  • the boiling point is more preferably 100°C or higher, and more preferably 230°C or lower.
  • the above boiling point refers to the boiling point at normal pressure.
  • the content of the solvent in the vehicle composition for dispersing inorganic particles is not particularly limited. % or more, preferably 90% by weight or less, more preferably 80% by weight or less, and even more preferably 70% by weight or less.
  • the vehicle composition for dispersing inorganic particles may contain a dispersant, a thixotropic agent, and the like in addition to the (meth)acrylic resin, the terpene compound, and the solvent.
  • the method for producing the vehicle composition for dispersing inorganic particles is not particularly limited.
  • the (meth)acrylic resin is produced in the presence of the terpene compound, the (meth)acrylic acid ester and the solvent are included.
  • a (meth)acrylic resin composition obtained by adding a polymerization initiator to a raw material monomer mixture and polymerizing the raw material monomer mixture to produce a (meth)acrylic resin can be used as a vehicle composition for dispersing inorganic particles. .
  • the method of stirring and mixing the said solvent and the other component added as needed to the said (meth)acrylic resin composition using 3 rolls etc. is mentioned.
  • the (meth)acrylic resin composition obtained in the production of the (meth)acrylic resin is stirred and mixed with the solvent, the terpene compound, and other components that are optionally added using a triple roll or the like. and the like.
  • a method of removing unreacted monomers and the like from the (meth)acrylic resin composition obtained by producing the above (meth)acrylic resin, and adding and mixing a solvent and the like may also be used.
  • the polymerization initiator is added so that the amount of active oxygen in the polymerization initiator is 0.04 parts by weight or more and 0.3 parts by weight or less with respect to 100 parts by weight of the raw material monomer mixture.
  • a method for producing a vehicle composition for dispersing inorganic particles is also one aspect of the present invention.
  • An inorganic particle-dispersed slurry composition can be produced by adding inorganic particles, a plasticizer, and optionally other components to the inorganic particle-dispersing vehicle composition.
  • the inorganic particle-dispersing vehicle composition and the inorganic particle-dispersed slurry composition containing the inorganic particles are also aspects of the present invention.
  • the inorganic particle-dispersed slurry composition contains inorganic particles.
  • the inorganic particles are not particularly limited, and examples thereof include ceramic powder, glass powder, phosphor particles, silicon oxide, metal particles, and the like.
  • the ceramic powder is not particularly limited, and examples thereof include alumina, ferrite, zirconia, zircon, barium zirconate, calcium zirconate, titanium oxide, barium titanate, strontium titanate, calcium titanate, magnesium titanate, zinc titanate, Lanthanum titanate, neodymium titanate, lead zirconium titanate, alumina nitride, silicon nitride, boron nitride, boron carbide, barium stannate, calcium stannate, magnesium silicate, mullite, steatite, cordierite, forsterite, etc. be done.
  • MnO3 , PbZrTiO3 , SrBi2Ta2O9 , BiFeO3 , KNbO3 , PbVO3 , BiCo3 , Bi (Zn1 /2Ti1 / 2) 3 and the like can also be used.
  • the glass powder is not particularly limited .
  • Examples include glass powders of various silicon oxides such as 3- SiO 2 system and LiO 2 -Al 2 O 3 -SiO 2 system.
  • R is an element selected from the group consisting of Zn, Ba, Ca, Mg, Sr, Sn, Ni, Fe and Mn.
  • glass powder of PbO-B 2 O 3 -SiO 2 mixture, BaO-ZnO-B 2 O 3 -SiO 2 mixture or ZnO-Bi 2 O 3 -B 2 O 3 -SiO 2 mixture containing no lead, etc. of lead-free glass powder is preferred.
  • the phosphor particles are not particularly limited, and examples of the phosphor material include blue phosphor material, red phosphor material, green phosphor material, and the like, which are conventionally known as phosphor materials for displays.
  • examples of blue phosphor materials include MgAl 10 O 17 :Eu, Y 2 SiO 5 :Ce-based, CaWO 4 :Pb-based, BaMgAl 14 O 23 :Eu-based, BaMgAl 16 O 27 :Eu-based, BaMg 2 Al 14 .
  • BaMg 2 Al 14 O 27 Eu system
  • ZnS: (Ag, Cd) system is used.
  • red phosphor materials include Y2O3 : Eu system, Y2SiO5 :Eu system, Y3Al5O12 :Eu system, Zn3 ( PO4 ) 2 :Mn system, YBO3 : Eu . (Y,Gd)BO 3 :Eu system, GdBO 3 :Eu system, ScBO 3 :Eu system, and LuBO 3 :Eu system.
  • Green phosphor materials include, for example, Zn2SiO4 :Mn-based , BaAl12O19 :Mn - based , SrAl13O19 :Mn-based, CaAl12O19 :Mn-based, YBO3 :Tb-based, and BaMgAl14O .
  • ZnO Zn system
  • ZnS (Cu, Al) system
  • ZnS Ag system
  • Y 2 O 2 S Eu system
  • ZnS Zn system
  • (Y, Cd) BO 3 Eu system
  • BaMgAl 12 O 23 Eu-based ones
  • the metal particles are not particularly limited, and examples thereof include powders of copper, nickel, palladium, platinum, gold, silver, aluminum, tungsten, alloys thereof, and the like.
  • metals such as copper and iron, which have good adsorption properties with carboxyl groups, amino groups, amide groups, etc. and are easily oxidized, can also be suitably used. These metal powders may be used alone or in combination of two or more.
  • various carbon blacks, carbon nanotubes, and the like may also be used.
  • LiTi2 ( PO4 ) 3 lithium titanate ( Li4Ti5O12 ), Li4 / 3Ti5 / 3O4 , LiCoO2 , lithium germanium phosphate ( LiGe2 ( PO4 ) 3 ) , Li 2 —SiS based glass, Li 4 GeS 4 —Li 3 PS 4 based glass, LiSiO 3 , LiMn 2 O 4 , Li 2 SP 2 S 5 based glass/ceramics, Li 2 O—SiO 2 , Li 2 O—V 2 O 5 —SiO 2 , LiS—SiS 2 —Li 4 SiO 4 based glass, ion conductive oxides such as LiPON, Li 2 O—P 2 O 5 —B 2
  • the content of the inorganic particles in the inorganic particle-dispersed slurry composition is not particularly limited, but is preferably 10% by weight or more, more preferably 20% by weight or more, preferably 90% by weight or less, and more preferably 60% by weight or less. 50% by weight or less is more preferable, and 45% by weight or less is even more preferable. When it is within the above range, it can have sufficient viscosity, can have excellent coatability, and can have excellent dispersibility of inorganic particles.
  • the inorganic particle-dispersed slurry composition preferably contains a plasticizer.
  • the plasticizer include di(butoxyethyl) adipate, dibutoxyethoxyethyl adipate, triethylene glycol bis(2-ethylhexanoate), triethylene glycol dihexanoate, acetyl tributyl citrate, acetyl triethyl citrate, dibutyl sebacate and the like.
  • non-aromatic plasticizer it is preferable to use a non-aromatic plasticizer, and it is more preferable to contain a component derived from adipic acid, triethylene glycol or citric acid.
  • a plasticizer having an aromatic ring is not preferable because it is likely to burn and become soot.
  • the plasticizer what has a C4 or more alkyl group is preferable.
  • the plasticizer suppresses the absorption of water into the plasticizer and prevents defects such as voids and swelling in the resulting inorganic particle-dispersed sheet. can do.
  • the alkyl group of the plasticizer is preferably located at the molecular terminal.
  • the plasticizer preferably has a carbon:oxygen ratio of 5:1 to 3:1.
  • the carbon:oxygen ratio By setting the carbon:oxygen ratio within the above range, it is possible to improve the combustibility of the plasticizer and prevent the generation of residual carbon. Moreover, compatibility with (meth)acrylic resin can be improved, and a plasticizing effect can be exhibited even with a small amount of plasticizer.
  • high-boiling organic solvents having a propylene glycol skeleton or a trimethylene glycol skeleton can be preferably used as long as they contain an alkyl group having 4 or more carbon atoms and have a carbon:oxygen ratio of 5:1 to 3:1.
  • the boiling point of the plasticizer is preferably 240°C or higher and lower than 390°C.
  • the boiling point refers to the boiling point at normal pressure.
  • the content of the plasticizer in the inorganic particle-dispersed slurry composition is not particularly limited, but is preferably 0.1% by weight or more, more preferably 0.5% by weight or more, further preferably 1% by weight or more, and 3.0% by weight. % by weight or less is preferable, 2.5% by weight or less is more preferable, and 2% by weight or less is even more preferable. By setting it within the above range, it is possible to reduce the baking residue of the plasticizer.
  • the inorganic particle-dispersed slurry composition may contain an additive such as a surfactant.
  • the surfactant is not particularly limited, and examples thereof include cationic surfactants, anionic surfactants, and nonionic surfactants.
  • the nonionic surfactant is not particularly limited, it is preferably a nonionic surfactant having an HLB value of 10 or more and 20 or less.
  • the HLB value is used as an index representing the hydrophilicity and lipophilicity of a surfactant, and several calculation methods have been proposed. is defined as S, the acid value of the fatty acid constituting the surfactant as A, and the HLB value as 20 (1-S/A).
  • nonionic surfactants having polyethylene oxide in which an alkylene ether is added to the fatty chain are suitable, and specifically, for example, polyoxyethylene lauryl ether, polyoxyethylene cetyl ether, etc. are preferably used. be done.
  • the above nonionic surfactant has good thermal decomposability, but if added in a large amount, the thermal decomposability of the inorganic particle-dispersed slurry composition may decrease, so the content is preferably 5% by weight or less.
  • the content of the (meth)acrylic resin in the inorganic particle-dispersed slurry composition is not particularly limited, but is preferably 1% by weight or more, more preferably 3% by weight or more, further preferably 5% by weight or more, and 30% by weight or less. is preferred, 20% by weight or less is more preferred, and 10% by weight or less is even more preferred. Within the above range, it is possible to obtain an inorganic particle-dispersed slurry composition that can be degreased even when fired at a low temperature.
  • the content of the terpene compound in the inorganic particle-dispersed slurry composition is preferably 0.02 parts by weight or more and preferably 1.8 parts by weight or less with respect to 100 parts by weight of the (meth)acrylic resin.
  • the content of the terpene compound can be measured by, for example, GC-MS.
  • the content of the solvent in the inorganic particle-dispersed slurry composition is not particularly limited, but is preferably 40% by weight or more, more preferably 45% by weight or more, still more preferably 50% by weight or more, and preferably 80% by weight or less. % by weight or less is more preferable, and 65% by weight or less is even more preferable. Within the above range, the coatability and the dispersibility of the inorganic particles can be improved.
  • the content of the solvent in the inorganic particle-dispersed slurry composition is preferably 100 parts by weight or more, more preferably 120 parts by weight or more, and 150 parts by weight with respect to 100 parts by weight of the (meth)acrylic resin. It is more preferably 300 parts by weight or less, more preferably 270 parts by weight or less, and even more preferably 250 parts by weight or less.
  • the inorganic particle-dispersed slurry composition may contain a dispersant, a thixotropic agent, or the like.
  • the viscosity of the inorganic particle-dispersed slurry composition is not particularly limited, but the viscosity measured at 20° C. using a Brookfield viscometer with the probe rotation speed set to 5 rpm is preferably 0.1 Pa ⁇ s or more. , 100 Pa ⁇ s or less.
  • the viscosity is preferably 0.1 Pa ⁇ s or more. , 100 Pa ⁇ s or less.
  • the method for producing the inorganic particle-dispersed slurry composition is not particularly limited, and conventionally known methods can be mentioned. a method of stirring and mixing the above solvent and other components added depending on the conditions using a three-roll roller or the like.
  • the inorganic particle-dispersed slurry composition containing the vehicle composition for dispersing inorganic particles is coated on a support film that has been subjected to mold release treatment on one side, the solvent is dried, and the inorganic particle-dispersed sheet is formed by forming into a sheet. can be manufactured. Further, a step of degreasing may be performed at a temperature of 300° C. or more and 350° C. or less in an oxygen atmosphere.
  • a method for producing an inorganic particle-dispersed sheet which includes a step of degreasing at a temperature of 300° C. or higher and 350° C. or lower in an oxygen atmosphere using the vehicle composition for dispersing inorganic particles, is also one aspect of the present invention.
  • the inorganic particle-dispersed sheet which is another embodiment of the present invention, preferably has a thickness of 1 to 20 ⁇ m.
  • the method for producing the inorganic particle-dispersed sheet includes, for example, a method in which the inorganic particle-dispersed slurry composition is applied to form a uniform coating film on a support film by a coating method such as a roll coater, a die coater, a squeeze coater, a curtain coater, or the like. etc.
  • a coating method such as a roll coater, a die coater, a squeeze coater, a curtain coater, or the like. etc.
  • the resulting (meth)acrylic resin composition is used as a vehicle composition for dispersing inorganic particles without drying, and then a plasticizer, inorganic particles, a solvent, etc. are added to obtain inorganic particles. It is preferable to process the dispersion slurry composition into an inorganic particle dispersion sheet.
  • (meth)acrylic resin is dried, undried particles called particles are generated when it is resolubilized, and such particles are difficult to remove even by filtration using a cartridge filter
  • the support film used for producing the inorganic particle-dispersed sheet is preferably a flexible resin film having heat resistance and solvent resistance. Since the support film has flexibility, the inorganic particle-dispersed slurry composition can be applied to the surface of the support film by a roll coater, a blade coater, or the like, and the resulting inorganic particle-dispersed sheet-forming film is wound into a roll. It can be stored and supplied as is.
  • the resin forming the support film examples include fluorine-containing resins such as polyethylene terephthalate, polyester, polyethylene, polypropylene, polystyrene, polyimide, polyvinyl alcohol, polyvinyl chloride, and polyfluoroethylene, nylon, and cellulose.
  • the thickness of the support film is preferably 20 to 100 ⁇ m, for example.
  • it is preferable that the surface of the support film is subjected to a release treatment, so that the support film can be easily peeled off in the transfer step.
  • the drying temperature is preferably 80° C. or higher and 120° C. or lower. Even if a solvent with a high boiling point is used, it can be dried by blowing air even at a low temperature.
  • An electronic component can be produced by using the inorganic particle-dispersed slurry composition and the inorganic particle-dispersed sheet.
  • a multilayer ceramic capacitor can be produced by using the inorganic particle-dispersed slurry composition and the inorganic particle-dispersed sheet as electrode pastes and dielectric green sheets.
  • a method for producing an electronic component which includes a step of degreasing at a temperature of 300° C. or higher and 400° C. or lower using the inorganic particle-dispersed slurry composition, is also one aspect of the present invention.
  • an inorganic particle dispersed sheet containing ceramic powder such as barium titanate as inorganic particles can be used as the dielectric green sheet.
  • an inorganic particle-dispersed slurry composition containing metal particles such as nickel as inorganic particles can be used as the electrode paste.
  • the electrode paste is printed on the dielectric green sheet and dried to form a dielectric sheet.
  • a method for printing the electrode paste is not particularly limited, and examples thereof include a screen printing method, a die coat printing method, an offset printing method, a gravure printing method, an inkjet printing method, and the like.
  • the obtained dielectric sheets are laminated, hot-pressed, and punched into a predetermined size to form a laminated body.
  • the punched laminate is degreased and fired in a firing furnace to decompose and remove organic components such as (meth)acrylic resin.
  • the degreasing temperature is preferably 300° C. or higher, and preferably 400° C. or lower.
  • the firing temperature can be selected according to the melting point of the inorganic particles.
  • the firing is preferably carried out in a reducing atmosphere so as not to oxidize the internal electrodes. For example, when barium titanate is used as the inorganic particles, firing at 1100° C. for 3 hours can yield a multilayer ceramic capacitor. can.
  • a vehicle composition for dispersing inorganic particles which can be degreased at a lower temperature in a shorter time and has excellent viscosity stability. Further, it is possible to provide a method for producing a vehicle composition for dispersing inorganic particles, an inorganic particle-dispersed slurry, and a method for producing an electronic component.
  • MMA methyl methacrylate
  • iBMA isobutyl methacrylate
  • PPOMA polypropylene glycol monomethacrylate
  • Examples 7 to 10, Comparative Examples 1 and 5 Monomers were mixed so as to have the composition shown in Table 1, and 100 parts by weight of an acrylic monomer, 100 parts by weight of a solvent shown in Table 1, and additives of the types and amounts shown in Table 1 were mixed to obtain a monomer mixed solution. . Furthermore, a vehicle composition for dispersing inorganic particles was prepared in the same manner as in Example 1, except that the polymerization initiator and solvent were added in several portions so that the total amount of addition was as shown in Table 1. A vehicle composition for dispersing inorganic particles and a slurry composition for dispersing inorganic particles were prepared in the same manner as in Example 1, except that the solvent and inorganic particles were added so as to have the formulations shown in Table 2.
  • Example 2 Preparation of vehicle composition for dispersing inorganic particles
  • a flask was charged with 30 parts by weight of n-butyl methacrylate (nBMA), 60 parts by weight of isobutyl methacrylate (iBMA), and 10 parts by weight of isodecyl methacrylate (iDMA).
  • nBMA n-butyl methacrylate
  • iBMA isobutyl methacrylate
  • iDMA isodecyl methacrylate
  • 20 parts by weight of methyl ethyl ketone as a solvent and 1.6 parts by weight of myrcene as a terpene compound having two or more double bonds were mixed to obtain a monomer mixture.
  • inorganic particle dispersion slurry composition green sheet resin composition
  • barium titanate (“BT-02”, manufactured by Sakai Chemical Industry Co., Ltd.) was added as inorganic particles.
  • average particle size of 0.2 ⁇ m) and acetyl tributyl citrate as a plasticizer were added so as to have the formulation shown in Table 2, and mixed using a ball mill to obtain an inorganic particle-dispersed slurry composition.
  • the slurry composition contains a very small amount of residual monomers that have not been polymerized into the polymer and decomposition residues of the initiator, but these are regarded as the weight of the solvent.
  • inorganic particle-dispersed sheet green sheet
  • the obtained inorganic particle-dispersed slurry composition is applied onto a release-treated polyester film so that the thickness after drying becomes 50 ⁇ m, and the mixture is kept at room temperature for 1 hour. After drying, it was dried at 80° C. for 3 hours using a hot air dryer to prepare an inorganic particle-dispersed sheet.
  • Examples 3-6, Comparative Examples 2-4 Monomers were mixed so as to have the composition shown in Table 1, and 100 parts by weight of an acrylic monomer, 20 parts by weight of a solvent shown in Table 1, and additives of the type and amount shown in Table 1 were mixed to obtain a monomer mixed solution. . Further, a resin composition was prepared in the same manner as in Example 1 except that the polymerization initiator and the solvent were added in several batches so that the total amount of addition was as shown in Table 1.
  • a vehicle composition for dispersing inorganic particles, a slurry composition for dispersing inorganic particles, and an inorganic particle-dispersed sheet were prepared in the same manner as in Example 2 except that the solvent, inorganic particles, and plasticizer were added so as to have the formulations shown in Table 2. made.
  • EMA n-ethyl methacrylate
  • nBMA n-butyl methacrylate
  • EHMA 2-ethylhexyl methacrylate
  • iDMA isodecyl methacrylate
  • HEMA hydroxyethyl methacrylate
  • Polymer conversion rate (%) [resin solid content (%) / solid content (%) when monomer is 100% polymer] ⁇ 100 ⁇ : polymer conversion rate is 96% or more and 100% or less ⁇ : polymer conversion rate is 90% or more and less than 96% ⁇ : polymer conversion rate is less than 90%
  • Viscosity change rate (%) [(Viscosity after 2 weeks - Viscosity immediately after preparation) / (Viscosity immediately after preparation)] ⁇ 100 ⁇ : Viscosity change rate is less than 10% ⁇ : Viscosity change rate is 10% or more and less than 20% ⁇ : Viscosity change rate is 20% or more
  • Decomposition start temperature is less than 220 ° C.
  • Decomposition start temperature is 220 ° C. or higher and less than 240 ° C.
  • Decomposition start temperature is 240 ° C. or higher (sintering residue)
  • the sample is white with almost no coloration.
  • ⁇ The sample was colored in beige or yellow.
  • x The sample was colored brown or black.
  • a conductive paste composed of silver, terpineol, and ethyl cellulose was produced.
  • a conductive paste was applied to the sintered body obtained using the dipping method, and sintered at 1250° C. for 3 hours to produce a multilayer ceramic capacitor (laminate 1).
  • Laminated ceramic capacitors (Laminates 2 to 9) were produced in the same manner as in “(Preparation of Laminate 1)” except that the ceramic green sheets and conductive paste films were prepared using the inorganic particle-dispersed slurry composition shown in Table 4. bottom.
  • ESR Equivalent series resistance
  • 10 multilayer ceramic capacitors were produced by the above method, and the multilayer ceramic capacitors were heat-treated in an air atmosphere at 150°C for 1 hour, then mounted on a measurement substrate, and 24 ⁇ 2 hours after the completion of the heat treatment, the network Equivalent series resistance (ESR) was measured using an analyzer. The measurement frequency was 10 MHz. Finally, the values for 10 pieces (for each condition) were averaged and evaluated according to the following criteria. ⁇ : ESR is less than 48 m ⁇ ⁇ : ESR is 48 m ⁇ or more
  • a vehicle composition for dispersing inorganic particles which can be degreased at a lower temperature in a shorter time and has excellent viscosity stability. Further, it is possible to provide a method for producing a vehicle composition for dispersing inorganic particles, an inorganic particle-dispersed slurry, and a method for producing an electronic component.
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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH08111346A (ja) * 1994-10-06 1996-04-30 Sumitomo Metal Mining Co Ltd 積層セラミックコンデンサー内部電極用ペースト
JPH09174579A (ja) * 1995-11-30 1997-07-08 Atohaas Holding Cv 重合性組成物から成形することにより得られる物品にカラーコントラストを形成する方法
JPH09174578A (ja) * 1995-11-30 1997-07-08 Atohaas Holding Cv 重合性組成物から成形することにより得られる物品にカラーコントラストを形成する方法および着色組成物
JP2020012013A (ja) * 2018-07-12 2020-01-23 公立大学法人大阪 熱分解性バインダー用のメタクリル酸エステル系ポリマー及び製品の製造方法

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH08111346A (ja) * 1994-10-06 1996-04-30 Sumitomo Metal Mining Co Ltd 積層セラミックコンデンサー内部電極用ペースト
JPH09174579A (ja) * 1995-11-30 1997-07-08 Atohaas Holding Cv 重合性組成物から成形することにより得られる物品にカラーコントラストを形成する方法
JPH09174578A (ja) * 1995-11-30 1997-07-08 Atohaas Holding Cv 重合性組成物から成形することにより得られる物品にカラーコントラストを形成する方法および着色組成物
JP2020012013A (ja) * 2018-07-12 2020-01-23 公立大学法人大阪 熱分解性バインダー用のメタクリル酸エステル系ポリマー及び製品の製造方法

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