WO2023195406A1 - Liant organique de moule, et composition de sable de moulage et moule obtenus à l'aide de celui-ci - Google Patents

Liant organique de moule, et composition de sable de moulage et moule obtenus à l'aide de celui-ci Download PDF

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Publication number
WO2023195406A1
WO2023195406A1 PCT/JP2023/013085 JP2023013085W WO2023195406A1 WO 2023195406 A1 WO2023195406 A1 WO 2023195406A1 JP 2023013085 W JP2023013085 W JP 2023013085W WO 2023195406 A1 WO2023195406 A1 WO 2023195406A1
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Prior art keywords
mold
compound
organic binder
molds
foundry sand
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PCT/JP2023/013085
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English (en)
Japanese (ja)
Inventor
靖英 石田
彰伸 深津
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旭有機材株式会社
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Publication of WO2023195406A1 publication Critical patent/WO2023195406A1/fr

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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B22—CASTING; POWDER METALLURGY
    • B22C—FOUNDRY MOULDING
    • B22C1/00—Compositions of refractory mould or core materials; Grain structures thereof; Chemical or physical features in the formation or manufacture of moulds
    • B22C1/02—Compositions of refractory mould or core materials; Grain structures thereof; Chemical or physical features in the formation or manufacture of moulds characterised by additives for special purposes, e.g. indicators, breakdown additives
    • B22C1/10—Compositions of refractory mould or core materials; Grain structures thereof; Chemical or physical features in the formation or manufacture of moulds characterised by additives for special purposes, e.g. indicators, breakdown additives for influencing the hardening tendency of the mould material
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B22—CASTING; POWDER METALLURGY
    • B22C—FOUNDRY MOULDING
    • B22C1/00—Compositions of refractory mould or core materials; Grain structures thereof; Chemical or physical features in the formation or manufacture of moulds
    • B22C1/16—Compositions of refractory mould or core materials; Grain structures thereof; Chemical or physical features in the formation or manufacture of moulds characterised by the use of binding agents; Mixtures of binding agents
    • B22C1/20—Compositions of refractory mould or core materials; Grain structures thereof; Chemical or physical features in the formation or manufacture of moulds characterised by the use of binding agents; Mixtures of binding agents of organic agents
    • B22C1/22—Compositions of refractory mould or core materials; Grain structures thereof; Chemical or physical features in the formation or manufacture of moulds characterised by the use of binding agents; Mixtures of binding agents of organic agents of resins or rosins
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B22—CASTING; POWDER METALLURGY
    • B22C—FOUNDRY MOULDING
    • B22C9/00—Moulds or cores; Moulding processes
    • B22C9/12—Treating moulds or cores, e.g. drying, hardening
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/54—Polycondensates of aldehydes

Definitions

  • the present invention relates to an organic binder for molds used in the production of phenol urethane-based gas-curing molds or self-hardening molds used in sand mold manufacturing, and to molding sand compositions and molds obtained using the same. .
  • phenol molds have been used as one of the typical organic molds used in sand casting, using phenolic resin and polyisocyanate compounds as binders, and making use of their polyaddition reaction (urethanization reaction).
  • Urethane molds are known.
  • Such phenol urethane molds include mass-produced gas-hardening molds manufactured by the cold box method that do not require heating during molding, and non-mass-produced self-hardening molds manufactured by the room-temperature self-hardening method. widely known.
  • gas-curing molds made by the cold box method are usually made by mixing granular refractory foundry sand with an organic binder for molds consisting of a phenolic resin solution and a polyisocyanate compound solution in an organic solvent using a mixer. After producing a foundry sand composition in which the surface of foundry sand is coated with an organic binder by kneading, the foundry sand composition is blown into a predetermined mold to form a mold. It is manufactured by curing by passing a catalyst gas such as amine gas.
  • the problem to be solved by the present invention is to provide an organic binder for molds that exhibits excellent fast curing properties when cured at room temperature and is capable of shortening molding time.
  • Another object of the present invention is to provide a foundry sand composition and a mold obtained using such an organic binder for molds.
  • the present invention can be suitably implemented in various embodiments as listed below. It is understood that the aspects and technical features of the present invention are not limited to those described below, but can be recognized based on the inventive idea that can be understood from the description of the specification. Should.
  • the compound a contains one or more selected from the group consisting of glycol oligomers, glyceryl ethers of glycol oligomers, fatty acid polycondensates, glyceryl ethers of fatty acid polycondensates, and glyceryl esters of fatty acid polycondensates.
  • Organic binder is polyoxyethylene glyceryl ether, polyoxypropylene glyceryl ether, glyceryl ether of ricinoleic acid polycondensate, or glyceryl ester of ricinoleic acid polycondensate.
  • a polyisocyanate compound and a predetermined compound are reacted together as an isocyanate group-containing compound that reacts with the phenol resin and an organic solvent.
  • the product is an essential component, it exhibits excellent fast curing properties when molding molds according to the cold box method or room temperature self-hardening method, which does not require heating during molding. A reduction in molding time can advantageously be achieved.
  • triethylamine (TEA ) and other amines making it an organic binder for molds that advantageously reduces the burden on the environment.
  • FIG. 2 is an explanatory diagram schematically showing a molding device used when evaluating fast curing properties.
  • the phenolic resin used as one of the main components in the organic binder for molds according to the present invention is not particularly limited, and has conventionally been used when molding phenol urethane molds.
  • Various known phenolic resins can be used as appropriate.
  • phenols and aldehydes are mixed in such a way that the ratio of aldehyde is generally about 0.5 to 3.0 mol per 1 mol of phenol.
  • examples include benzyl ether type phenolic resins, resol type phenolic resins, novolak type phenolic resins, and modified phenolic resins thereof, which are obtained by addition/condensation reactions, and mixtures thereof, which are soluble in organic solvents.
  • orthocresol-modified phenolic resins modified with orthocresol more preferably benzyl ether-type orthocresol-modified phenolic resins, and mixtures thereof are particularly important because of their solubility in organic solvents and their compatibility with polyisocyanates. It is preferably used in the present invention because it not only has excellent compatibility, but also can effectively improve the strength (initial strength) of the mold obtained.
  • the catalyst used in the above addition/condensation reaction between phenols and aldehydes is not particularly limited, and depending on the type of phenol resin desired, known acidic catalysts and bases may be used.
  • various catalysts conventionally used in the production of phenolic resins can be used as appropriate.
  • catalysts include metal salts containing metal elements such as tin, lead, zinc, cobalt, manganese, and nickel; more specifically, lead naphthenate, zinc naphthenate, Examples include lead acetate, zinc chloride, zinc acetate, zinc borate, lead oxide, and combinations of acids and bases that can form such metal salts.
  • the amount used is not particularly limited, but is generally about 0.01 to 5 parts by weight per 100 parts by weight of the phenol. It will be used at the same rate.
  • phenols that provide phenolic resins include alkylphenols such as phenol, cresol, xylenol, p-tert-butylphenol, and nonylphenol, polyhydric phenols such as resorcinol, bisphenol F, and bisphenol A, and mixtures thereof.
  • aldehydes include formaldehyde, formalin, paraformaldehyde, polyoxymethylene, glyoxal, furfural, and mixtures thereof.
  • orthocresol-modified phenolic resin which is one of the phenolic resins that can be advantageously employed in the present invention
  • orthocresol and phenol can be combined in the presence of a reaction catalyst such as a metal salt
  • a reaction catalyst such as a metal salt
  • cocondensation orthocresol modified phenolic resin of orthocresol and phenol (2) mixed orthocresol modified phenolic resin of orthocresol resin and phenol resin, which are obtained by reacting with aldehydes, these ( (3) modified orthocresol modified phenolic resin, which is obtained by modifying the resins of 1) and (2) with a modifier (modifier), and 2 of (1), (2), and (3)
  • modified orthocresol modified phenolic resin which is obtained by modifying the resins of 1) and (2) with a modifier (modifier), and 2 of (1), (2), and (3) Examples include mixtures of more than one species.
  • the co-condensed orthocresol-modified phenolic resin of (1) above is a co-condensed resin obtained by reacting orthocresol and phenol simultaneously or stepwise with aldehydes, Depending on the reaction conditions such as the type of reaction catalyst used, novolac type, resol type, benzyl ether type, and cocondensation type orthocresol modified phenolic resins that are a combination of these types can be obtained.
  • a benzyl ether type cocondensation type orthocresol modified phenol resin is preferably used.
  • the mixed orthocresol-modified phenolic resin (2) above is at least one selected from the group of novolak-type, resol-type, and benzyl ether-type orthocresol resins obtained by reacting orthocresol with aldehydes. Obtained by mixing a seed orthocresol resin with at least one phenolic resin selected from the group of novolac-type, resol-type and benzyl ether-type phenolic resins obtained by reacting phenol and aldehydes. It is something.
  • a benzyl ether type mixed orthocresol modified phenol resin which is a mixture of a benzyl ether type orthocresol resin and a benzyl ether type phenol resin, is preferably used.
  • the orthocresol resin and phenol resin are mixed so that the blending ratio of orthocresol and phenol is within the range mentioned above.
  • they are preferably mixed at a ratio of orthocresol resin/phenol resin (weight ratio) of 5/95 to 95/5, more preferably 20/80 to 80/20.
  • modified orthocresol-modified phenolic resin (3) can be further treated with any optional additive during or after the production of the co-condensed orthocresol-modified phenolic resin, orthocresol resin, or phenolic resin.
  • Modifiers such as alkyd resins, epoxy resins, melamine resins, urea resins, xylene resins, vinyl acetate resins, polyamide resins, urea compounds, melamine compounds, epoxy compounds, furfuryl alcohol, polyvinyl alcohol , urea, amides, linseed oil, cashew nut shell liquid, rosin, starch, monosaccharides, etc., modified by mixing or reacting with them, selected from the group of novolac type, resol type and benzyl ether type resins. At least one type of modified orthocresol modified phenolic resin. Among these, benzyl ether-type modified orthocresol-modified phenol resins are advantageously used in the present invention.
  • the phenolic resin used as one of its main components has the following properties: low viscosity, compatibility with the polyisocyanate solution described below, coating properties on foundry sand, From the viewpoint of mold properties, etc., a solution (hereinafter referred to as "phenolic resin") is generally dissolved in an organic solvent consisting of a combination of a polar organic solvent and a non-polar organic solvent, and the concentration thereof is about 30 to 80% by weight. It is used in the form of a solution (referred to as "solution").
  • a polyisocyanate compound and compound a (a compound having 2 or 3 hydroxyl groups and/or carboxyl groups in the molecule and having a number average molecular weight of 300 to 3000.
  • reaction product with a compound in which the total number of hydroxyl groups and carboxyl groups contained in one molecule is 2 or 3), in which the proportion of compound a in the reaction product is 0.1 to 10.0 mass % (hereinafter also simply referred to as "reaction product") is used and constituted, which is a major technical feature. Since such a predetermined compound is used in place of a conventional polyisocyanate compound, the organic binder for molds according to the present invention can be used in a cold box method or room-temperature self-hardening method that does not require heating during molding. When used in mold manufacturing, it exhibits excellent rapid curing properties and advantageously shortens molding time.
  • a compound with a number average molecular weight that is too large or too small may be used as the compound a of the present invention.
  • a compound having 2 or 3 hydroxyl groups and/or carboxyl groups in the molecule and having a number average molecular weight of 300 to 3000 is used as compound a in the present invention.
  • the proportion of compound a in the reaction product of the polyisocyanate compound and compound a is preferably 0.1 to 12.0% by mass, more preferably 0.5 to 11% by mass. 0% by weight is used, most preferably 1.0-10.5% by weight.
  • the ratio of compound a to the polyisocyanate compound in the reaction product refers to the ratio of compound a to the amount (mass) of the polyisocyanate compound used when the polyisocyanate compound and compound a are reacted. It means the proportion of the amount used (mass).
  • any compound having 2 or 3 hydroxyl groups and/or carboxyl groups in the molecule and having a number average molecular weight of 300 to 3000 may be used as compound a without particular limitation.
  • polyoxyethylene glyceryl ether, polyoxypropylene glyceryl ether, glyceryl ether of ricinoleic acid polycondensate, or glyceryl ester of ricinoleic acid polycondensate which have a number average molecular weight of 300 to 3000, are used as compounds. By using it as a, it becomes possible to enjoy the effects of the present invention more advantageously.
  • aromatic, aliphatic or alicyclic polyisocyanates such as diphenylmethane diisocyanate, polymethylene polyphenylene polyisocyanate (hereinafter referred to as "polymeric MDI"), hexamethylene diisocyanate, 4,4'-dicyclohexylmethane
  • polymeric MDI polymethylene polyphenylene polyisocyanate
  • hexamethylene diisocyanate 4,4'-dicyclohexylmethane
  • various conventionally known polyisocyanate compounds can be mentioned, such as prepolymers having two or more isocyanate groups obtained by reacting these polyisocyanate compounds with polyols, and these can be used alone or in combination of two or more types. may be reacted with the above compound a in combination.
  • any conventionally known method can be used.
  • the polyisocyanate compound, compound a, and the organic solvent are held at room temperature (or while heating) for 12 hours or more, preferably about 24 to 72 hours, with sufficient stirring (or after sufficient stirring). By doing so, it is possible to cause the polyisocyanate compound and compound a to react.
  • the reaction product obtained in this way is generally made of a non-polar organic solvent or a mixed solvent of a non-polar organic solvent and a polar solvent. is used as a solution in which it is dissolved to a concentration of approximately 40 to 90% by weight.
  • the organic solvent for dissolving the above-mentioned phenolic resin and reaction product should be one that is non-reactive with the reaction product and a good solvent for the solute (phenol resin or reaction product) to be dissolved.
  • a polar solvent for dissolving the phenolic resin i) an amount for dissolving the reaction product that does not cause separation of the phenolic resin. It is used in combination with a non-polar solvent.
  • aliphatic carboxylic acid esters for example, aliphatic carboxylic acid esters, and among them, from the viewpoint of environmental safety, dicarboxylic acid methyl ester mixtures (manufactured by DuPont, trade name: DBE, Dicarboxylic acid alkyl esters such as dimethyl glutarate, dimethyl adipate, and dimethyl succinate), vegetable oil methyl esters such as rapeseed oil methyl ester, ethyl oleate, ethyl palmitate, mixtures thereof, fatty acid monoesters, etc.
  • esters examples thereof include ketones such as isophorone, ethers such as isopropyl ether, and furfuryl alcohol.
  • non-polar solvents in ii) above include petroleum-based hydrocarbons such as paraffins, naphthenes, and alkylbenzenes; specific examples include Ipsol 150 (IP150, manufactured by Idemitsu Kosan Co., Ltd., petroleum-based solvent); , Hysol 100 (made by ENEOS Co., Ltd., petroleum-based solvent), AF Solvent No. 4 (AF4, made by ENEOS Co., Ltd., petroleum-based solvent), HAWS (made by Shell Chemicals Japan Co., Ltd.; petroleum-based solvent), etc. I can do it.
  • Ipsol 150 IP150, manufactured by Idemitsu Kosan Co., Ltd., petroleum-based solvent
  • Hysol 100 made by ENEOS Co., Ltd., petroleum-based solvent
  • AF Solvent No. 4 AF4, made by ENEOS Co., Ltd., petroleum-based solvent
  • HAWS made by Shell Chemicals Japan Co., Ltd.; petroleum-based solvent
  • the organic binder for molds according to the present invention is composed of the above-mentioned phenolic resin solution and a solution containing a predetermined reaction product. It is also possible to appropriately select and blend various known additives used in binders. However, it goes without saying that these various additives need to be used in amounts that do not impede the effects that can be enjoyed by the present invention. Examples of additives that can be blended in the present invention include pot life extenders, strength deterioration inhibitors, mold release agents, and drying inhibitors.
  • a pot life extender is a component that has been traditionally used to suppress the urethanization reaction and extend the pot life of foundry sand compositions.
  • various known compounds are appropriately selected and used, such as isophthalic acid chloride, salicylic acid, benzoic acid, phosphoric acid, acidic phosphate ester, phosphorus chloride, boric acid, etc. I can list them.
  • the strength deterioration inhibitor is used to prevent mold strength from deteriorating in a humid environment and to improve the adhesion between the resin component of the organic binder and the foundry sand, and is a suitable agent.
  • examples include amino-based silanes such as N- ⁇ (aminoethyl)- ⁇ -aminopropyltrimethoxysilane and ⁇ -aminopropyltriethoxysilane, and epoxy-based silanes such as ⁇ -glycidoxypropyltrimethoxysilane.
  • Examples include silane coupling agents such as.
  • the amount of the strength deterioration inhibitor used is generally about 0.01 to 5 parts by mass, preferably about 0.05 to 2.5 parts by mass, per 100 parts by mass of the phenolic resin. , will be adopted.
  • the organic binder for molds according to the present invention is composed of the various components as described above, and a phenol urethane gas-curing mold or self-hardening mold is molded using this organic binder. This is what happens.
  • the organic binder for molds according to the present invention is mixed into the foundry sand, so that the surface of the foundry sand is coated with the organic binder for molds.
  • a foundry sand composition (kneaded sand) coated with a binder will be produced. That is, by sufficiently kneading and mixing foundry sand with a phenolic resin solution as an organic binder, a solution containing a predetermined reaction product, and other various additives as necessary.
  • a foundry sand composition is produced by coating the surface of foundry sand with an organic binder for molding.
  • the phenolic resin solution constituting the organic binder and the solution containing the predetermined reaction product are gradually subjected to polyaddition reaction (urethanization) from the stage of mixing them. reaction), they are prepared separately in advance and are usually mixed together when kneading with foundry sand. Further, the kneading/mixing operation is preferably carried out at a temperature of about -10 to 50°C using a conventional continuous or batch mixer.
  • the foundry sand composition obtained as described above is shaped in a mold such as a mold that gives a desired shape, and then a catalyst gas for curing is passed through the molding sand composition.
  • a catalyst gas for curing is passed through the molding sand composition.
  • the catalyst gas include conventionally known tertiary amine gases such as triethylamine, dimethylethylamine, and dimethylisopropylamine, as well as cyclic nitrogen compounds, pyridine, and N-ethylmorpholine. At least one kind is appropriately selected and used in a usual quantitative range.
  • a foundry sand composition is produced by coating the surface of the foundry sand with an organic binder.
  • a curing catalyst is further mixed together with the organic binder at the time of kneading.
  • the curing catalyst include bases, amines, metal ions, etc. that are commonly used in the known Ashland method.
  • the obtained foundry sand composition is cured by the added curing catalyst, and is immediately shaped in a mold that gives the desired shape to produce a self-hardening mold. That's what happens.
  • the blending amounts of the phenol resin solution and the solution containing the predetermined reaction products are as follows: A proportion is preferably adopted in which the blending amount of each product is about 0.01 to 5.0 parts by mass, preferably about 0.1 to 2.0 parts by mass, per 100 parts by mass of foundry sand. be done.
  • the foundry sand used in the present invention is not particularly limited, and may be natural sand or artificial sand as long as it is fire-resistant and has been conventionally used for molds. do not have.
  • silica sand, olivine sand, zircon sand, chromite sand, alumina sand, ferrochrome slag, ferronickel slag, converter slag, mullite artificial particles (for example, the product name available from Itochu Ceratec Corporation) Cerabeads”) and recycled sand thereof, and one or more of these may be used in combination.
  • mullite-based artificial particles which are spherical and have excellent crush resistance, are more preferably employed from the viewpoint of polishing regeneration treatment after mold recovery.
  • the gas-curing molds and self-hardening molds manufactured as described above effectively exhibit rapid curing properties during molding, and thus the molding time can be advantageously shortened.
  • it because it exhibits such excellent fast curing properties, it is possible to reduce the amount of amines used as catalyst gas, especially when manufacturing gas-cured molds using the cold box method, which is environmentally friendly. It is also possible to advantageously enjoy the effect of advantageously reducing the load on the vehicle.
  • phenolic resin solution A having a phenolic resin content of 50.0% by mass was prepared by dissolving using 0 parts by mass.
  • Solution I containing a reaction product of a polyisocyanate compound and a predetermined compound a was prepared according to the following procedure. That is, Polymeric MDI (MDI), which is a polyisocyanate compound, Ipsol 150 (IP150, manufactured by Idemitsu Kosan Co., Ltd., petroleum-based solvent), AF Solvent No. 4 (AF4, manufactured by ENEOS Co., Ltd., petroleum-based solvent), and the following. Compound a listed in Tables 1 to 3 are blended in the proportions shown in Tables 1 to 3 below, stirred thoroughly, and then maintained at a temperature of 25°C for two days (48 hours). Solution I according to each of the Examples and Comparative Examples was prepared. Regarding Solution I according to Comparative Example 1, compound a was not used, MDI, IP150, and AF4 were blended in the proportions shown in Table 3 below, and after thorough stirring, the solution was heated at 25°C for two days ( 48 hours).
  • MDI Polymeric MDI
  • IP150 manufactured by Idemitsu Ko
  • the test mold is immediately removed from the molding equipment, the side of the mold is hit with a rubber hammer, and the molding sand composition (cured and uncured molding sand composition; hereinafter simply referred to as the mixture) is poured out from inside the mold. ).
  • the molding sand composition cured and uncured molding sand composition; hereinafter simply referred to as the mixture
  • the mixture is poured out from inside the mold.
  • the cured product from the knocked-off mixture measure its weight: x (g), and measure the ratio of the weight of the cured product: x (g) to the weight (350 g) of the foundry sand composition accommodated in the mold. is calculated and set as the curing rate (%). It is judged that the larger the value of this curing rate (%), the better the rapid curing property.
  • phenolic resin solution B having a phenolic resin content of 58.0% by mass.

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Abstract

L'invention concerne un liant organique de moule qui présente une excellente propriété de durcissement rapide et peut raccourcir le temps de moulage lorsqu'un moule est fabriqué par durcissement à température ordinaire.　Le liant organique de moule utilisé pour mouler un moule à durcissement par gaz à base d'uréthane phénolique ou un moule à auto-durcissement est formé à l'aide, en tant que composants essentiels, d'une résine phénolique, d'un solvant organique et d'un produit de réaction de i) un composé polyisocyanate et ii) un composé a ayant deux ou trois groupes hydroxyle et/ou groupes carboxyle intramoléculaires et ayant une masse moléculaire moyenne en nombre de 300 à 3000, la proportion du composé a par rapport au composé polyisocyanate étant de 0,1 à 12,0 % en masse.
PCT/JP2023/013085 2022-04-04 2023-03-30 Liant organique de moule, et composition de sable de moulage et moule obtenus à l'aide de celui-ci WO2023195406A1 (fr)

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4946876A (en) * 1988-10-31 1990-08-07 Ashland Oil, Inc. Polyurethane-forming foundry binders containing a polyester polyol
JP2006272366A (ja) * 2005-03-28 2006-10-12 Asahi Organic Chem Ind Co Ltd 鋳型用有機粘結剤及びこれを用いて得られる鋳物砂組成物並びに鋳型

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4946876A (en) * 1988-10-31 1990-08-07 Ashland Oil, Inc. Polyurethane-forming foundry binders containing a polyester polyol
JP2006272366A (ja) * 2005-03-28 2006-10-12 Asahi Organic Chem Ind Co Ltd 鋳型用有機粘結剤及びこれを用いて得られる鋳物砂組成物並びに鋳型

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