WO2023139635A1 - Composition de résine d'uréthane - Google Patents

Composition de résine d'uréthane Download PDF

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Publication number
WO2023139635A1
WO2023139635A1 PCT/JP2022/001566 JP2022001566W WO2023139635A1 WO 2023139635 A1 WO2023139635 A1 WO 2023139635A1 JP 2022001566 W JP2022001566 W JP 2022001566W WO 2023139635 A1 WO2023139635 A1 WO 2023139635A1
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Prior art keywords
resin composition
urethane resin
composition according
foam
test
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PCT/JP2022/001566
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English (en)
Japanese (ja)
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慎一 江川
和久 永田
文隆 中村
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株式会社日本アクア
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Priority to PCT/JP2022/001566 priority Critical patent/WO2023139635A1/fr
Publication of WO2023139635A1 publication Critical patent/WO2023139635A1/fr

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    • 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
    • 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
    • C08G18/16—Catalysts
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
    • C08L75/04—Polyurethanes

Definitions

  • the present invention relates to a urethane resin composition and the like used as a heat insulating material for buildings.
  • a test device called a cone calorimeter is used in an exothermic test conforming to ISO-5660 for evaluating the flame retardancy of a urethane resin composition.
  • the cone calorimeter is equipped with a cone heater arranged above a specimen cut into a predetermined size, and a spark rod provided between the specimen and the cone heater.
  • combustible gas is generated from the test specimen by heating with a cone heater, and the combustible gas is ignited by the spark of the spark rod to generate combustion.
  • spark contact During the exothermic test, there were some specimens that swelled when heated by the cone heater, and it was sometimes confirmed that the swollen part of the specimen came into contact with the spark plug, or that discharge occurred even though the expanded specimen did not come into contact with the plug (these phenomena are hereinafter also referred to as "spark contact"). Test specimens with spark contact do not produce valid results when conforming to ISO-5660, so it is necessary to check the presence or absence of spark contact each time.
  • a urethane resin composition when used as a heat insulating material, there is also a problem that pressure is applied to an interior material (such as a gypsum board) provided around the heat insulating material due to swelling due to heating, resulting in breakage. If the interior material is damaged, the heat in the event of a fire is likely to be conducted to the heat insulating material, increasing the possibility that the exterior material will also be thermally affected.
  • an interior material such as a gypsum board
  • one of the objects of the present invention is to provide a urethane resin composition that is less likely to swell when heated.
  • the present invention is a urethane resin composition that forms a foam that constitutes a heat insulating material for buildings, which contains at least a polyisocyanate compound, a polyol compound, a trimerization catalyst, a foaming agent and a flame retardant, and does not contain a foam stabilizer and a surface conditioner.
  • a urethane resin composition that is less likely to swell when heated. Further, in a preferred embodiment of the present invention, it is possible to obtain a urethane resin composition that does not cause spark contact even in an exothermic test conforming to ISO-5660. Furthermore, in a preferred embodiment of the present invention, when used as a heat insulating material for a building, it is possible to obtain a urethane resin composition that does not cause the heat insulating material to swell beyond the clearance from the heat insulating material to the interior material, and does not cause the interior material to be pushed up and damaged. Furthermore, in a preferred embodiment of the present invention, it is possible to contribute to cost reduction by reducing the number of raw materials required for forming the urethane resin composition.
  • the urethane resin composition according to the present invention is for forming a foam that constitutes a heat insulating material for buildings, and contains at least a polyisocyanate compound, a polyol compound, a trimerization catalyst, a blowing agent, and a flame retardant, and does not contain a foam stabilizer and a surface conditioner.
  • the urethane resin composition according to the present invention may further contain mineral-derived materials such as clay minerals.
  • a heat insulating layer can be formed on a building by dividing the above composition into a polyisocyanate compound (first liquid) and other components (second liquid), and mixing and spraying the two, or by mixing and spraying the two.
  • the urethane resin composition according to the present invention can be provided with the following performances by adjusting the composition of each material.
  • Non-combustibility The urethane resin composition according to the present invention can have non-combustibility specified in the exothermic test based on the test of ISO-5660.
  • ⁇ 2.1.1> ISO-5660 test In the exothermic test conforming to ISO-5660, a test device called a cone calorimeter is used.
  • the cone calorimeter is equipped with a cone heater placed above a test piece cut to a predetermined size and a spark rod provided between the test piece and the cone heater.
  • the test piece is heated by the cone heater to generate combustible gas, which is ignited by the spark of the spark rod to cause combustion.
  • the urethane resin composition according to the present invention can have a swelling amount that does not cause spark contact when the ISO-5660 test is carried out.
  • the maximum expansion length in the height direction of the specimen should be less than 8 mm, more preferably 2 mm or less.
  • the urethane resin composition according to the present invention can have a foam density of 30 kg/m3 or more. By setting the density of the foam to 30 kg/m 3 or more, it is possible to obtain a sufficient effect of suppressing deformation against impact from other sources when used as a heat insulating material for buildings.
  • Polyisocyanate compound A polyisocyanate compound is a material used as a main ingredient in the urethane resin composition according to the present invention.
  • polyisocyanate compounds include aromatic polyisocyanates, alicyclic polyisocyanates, aliphatic polyisocyanates, and modified polyisocyanates.
  • aromatic polyisocyanate include phenylene diisocyanate, tolylene diisocyanate, xylylene diisocyanate, diphenylmethane diisocyanate, dimethyldiphenylmethane diisocyanate, triphenylmethane triisocyanate, naphthalene diisocyanate, and polymethylene polyphenyl polyisocyanate.
  • Examples of the alicyclic polyisocyanate include cyclohexyl diisocyanate, methylcyclohexyl diisocyanate, isophorone diisocyanate, dicyclohexylmethane diisocyanate, dimethyldicyclohexylmethane diisocyanate, and the like.
  • Examples of the aliphatic polyisocyanate include methylene diisocyanate, ethylene diisocyanate, propylene diisocyanate, tetramethylene diisocyanate, hexamethylene diisocyanate and the like.
  • the modified polyisocyanate is an isocyanate group-terminated prepolymer obtained by reacting a polyol component with a polyisocyanate compound, and includes urethane-modified products, carbodiimide-modified products, urea-modified products, burette-modified products, allophanate-modified products, and the like.
  • the polyisocyanate compound can be used alone or in combination of two or more.
  • polymethylene polyphenyl polyisocyanate polymeric MDI, crude MDI
  • polymeric MDI polymeric MDI, crude MDI
  • polymethylene polyphenyl polyisocyanate examples include Millionate MR-200, MR-100 and MR-400 manufactured by Tosoh, Sumidule 44V20L and Dismodur 44V20L manufactured by Covestro, PM-200 and PM-400 manufactured by Wanhua Chemical, and PAPI27 and PAPI135 manufactured by DOW.
  • the amount of polyisocyanate contained in the urethane resin composition is preferably such that the isocyanate index is 150-1000. When it is 150 or more, the flame retardancy is further improved, and when it is 1000 or less, the adhesion to the frame or the like is good.
  • the isocyanate index is most preferably in the range of 400-600.
  • the isocyanate index is calculated from the equivalent ratio of the isocyanate group contained in the isocyanate component to the active hydrogen contained in the polyol component and the water of the foaming agent. [Isocyanate group] / [OH group] (molar ratio) ⁇ 100
  • Polyol compound A polyol compound is a material used as a curing agent in the urethane resin composition according to the present invention.
  • the polyol compound consists of an ester-based polyol compound or an ether-based polyol compound and combinations thereof.
  • Ester Polyol compounds include, for example, polymers obtained by dehydration condensation of polybasic acids and polyhydric alcohols, polymers obtained by ring-opening polymerization of lactones such as ⁇ -caprolactone and ⁇ -methyl- ⁇ -caprolactone, and condensates of hydroxycarboxylic acids and the above polyhydric alcohols.
  • specific examples of the polybasic acid include adipic acid, azelaic acid, sebacic acid, terephthalic acid, isophthalic acid, and succinic acid. Modification with terephthalic acid is preferred in terms of flame retardancy.
  • polyol compounds examples include polylactone polyols, polycarbonate polyols, aromatic polyols, alicyclic polyols, aliphatic polyols, polymer polyols, polyether polyols, and the like.
  • polylactone polyols examples include polypropiolactone glycol, polycaprolactone glycol, and polyvalerolactone glycol.
  • polycarbonate polyols examples include polyols obtained by a dealcoholization reaction of a hydroxyl group-containing compound such as ethylene glycol, propylene glycol, butanediol, pentanediol, hexanediol, octanediol, and nonanediol with diethylene carbonate, dipropylene carbonate, and the like.
  • aromatic polyols include bisphenol A, bisphenol F, phenol novolak, cresol novolak and the like.
  • Examples of the alicyclic polyols include cyclohexanediol, methylcyclohexanediol, isophoronediol, dicyclohexylmethanediol, and dimethyldicyclohexylmethanediol.
  • Examples of the aliphatic polyols include ethylene glycol, propylene glycol, butanediol, pentanediol, and hexanediol.
  • polyhydric polyether polyols examples include ethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, 1,8-octanediol, 1,9-nonanediol, 3-methyl-1,5-pentanediol, and 3,3-dimethylolheptane.
  • polyether polyols obtained by addition polymerization of alkylene oxides such as ethylene oxide, propylene oxide and butylene oxide using a compound having two or more, preferably 3 to 8, active hydrogen groups such as aliphatic polyamines as an initiator, or polyether polyols obtained by ring-opening polymerization of alkyl glycidyl ethers such as methyl glycidyl ether, aryl glycidyl ethers such as phenyl glycidyl ether, and cyclic ether monomers such as tetrahydrofuran.
  • polyether polyols containing bromine, phosphorus, or the like may be used.
  • Mineral-derived materials are intended to improve flame retardancy and density.
  • a silicate compound is preferable as the mineral-derived material.
  • mineral-derived materials that can be used include montmorillonite, saponite, hectorite, vermiculite, kaolinite, mica, and talc.
  • Kaolin is an example of a material containing kaolinite as a main component. The kaolin also includes calcined kaolin obtained by treating kaolin at a high temperature. Calcined kaolin is suitable because of its small moisture content and small particle size distribution.
  • the content of the mineral-derived material is not particularly limited, it is preferably 15 to 85 parts by weight with respect to 100 parts by weight of the polyol compound.
  • the trimerization catalyst is a material for reacting and trimerizing the isocyanate groups contained in the polyisocyanate compound to promote the formation of isocyanurate rings.
  • the trimerization catalyst include nitrogen-containing aromatic compounds such as tris(dimethylaminomethyl)phenol, 2,4-bis(dimethylaminomethyl)phenol, and 2,4,6-tris(dialkylaminoalkyl)hexahydro-S-triazine; carboxylic acid alkali metal salts such as potassium acetate, potassium 2-ethylhexanoate and potassium octylate; and quaternary ammonium salts such as tetramethylammonium salts, tetraethylammonium salts and tetraphenylammonium salts.
  • a combination of an alkyl metal carboxylate and a quaternary ammonium salt is desirable from the standpoint of adhesion at low temperatures and flame retardancy.
  • Tosoh Toyocat-TRX, Toyocat-TRV, Toyocat-TR20, Evonik DABCO TMR, DABCO TMR-2, DABCO TMR-7, DABCO K-15, UCAT 18X, Polycat46, Kao KAOLIZER NO. 410, KAOLIZER NO. 420 and the like can be exemplified as trimerization catalysts.
  • the content of the trimerization catalyst is not particularly limited, it is preferably 1 to 20 parts by weight with respect to 100 parts by weight of the polyol compound.
  • the amount is 1 part by weight or more, the flame retardancy is further improved, and when the amount is 20 parts by weight or less, problems such as clogging of the mixing section of the spray gun due to excessive reaction can be suppressed.
  • the foaming agent is a material that promotes a decrease in the density of the molded product by generating gas inside the resin when the polyisocyanate compound (first liquid) and other components (second liquid) are mixed.
  • blowing agents include water. The reaction between isocyanate and water generates carbon dioxide, which is trapped inside the foam and accelerates the density reduction of the molded product.
  • foaming agents include those called physical foaming agents as listed below. Although it is liquid at room temperature, it gasifies inside the resin due to the exothermic reaction between isocyanate and polyol, accelerating the density reduction of the molded product.
  • dichloromonofluoroethane e.g., HCFC141b (1,1-dichloro-1-fluoroethane
  • HCFC22 chlorodifluoromethane
  • HCFC142b 1-chloro-1,1-difluoroethane
  • Hydrofluorocarbon HFC-245fa (1,1,1,3,3-pentafluoropropane) manufactured by Central Glass
  • HFC-365mfc (1,1,1,3,3-pentafluorobutane) manufactured by Honeywell, and the like.
  • nitrogen gas, oxygen gas, argon gas, carbon dioxide gas, etc. that can be dispersed or dissolved in the polyol component or the isocyanate component can be used as the foaming agent.
  • the content of the foaming agent is not particularly limited, it is preferably 1 to 100 parts by weight with respect to 100 parts by weight of the polyol. As the weight part of the foaming agent increases, the density of the foam decreases, but at the same time, the dimensional stability and compressive strength also decrease.
  • one or more of the foaming agents may be used.
  • a flame retardant is a material for imparting flame retardancy to the urethane resin composition according to the present invention.
  • the flame retardant is not particularly limited, but preferably includes at least one selected from the group consisting of red phosphorus, ammonium polyphosphate and phosphate ester in order to obtain high flame retardancy.
  • a combination of two or more kinds of ammonium polyphosphate or phosphate ester in addition to red phosphorus is preferable in terms of obtaining even higher flame retardancy.
  • Red Phosphorus Red phosphorus is a material for suppressing the total calorific value during combustion.
  • the red phosphorus used in the present invention is not limited, and commercially available products can be appropriately selected and used.
  • the content of the red phosphorus is not particularly limited, it is desirable to use 15 to 35 parts by weight of the red phosphorus with respect to 100 parts by weight of the polyol compound.
  • a phosphate-containing flame retardant like red phosphorus, is a material for suppressing the total calorific value during combustion.
  • the phosphate-containing flame retardant used in the present invention contains phosphoric acid.
  • Examples of the phosphate-containing flame retardant include salts of at least one metal or compound selected from the various phosphoric acids and metals of Groups IA to IVB of the periodic table, ammonia, aliphatic amines, and aromatic amines.
  • Examples of the metals of Groups IA to IVB of the periodic table include lithium, sodium, calcium, barium, iron (II), iron (III), and aluminum.
  • Examples of the aliphatic amine include methylamine, ethylamine, diethylamine, triethylamine, ethylenediamine and piperazine.
  • Examples of aromatic amines include pyridine, triazine, melamine, and ammonium.
  • the phosphate-containing flame retardant may be subjected to known water resistance improvement treatments such as silane coupling agent treatment and coating with melamine resin, or may be added with known foaming aids such as melamine and pentaerythritol.
  • the phosphate-containing flame retardant include monophosphates, pyrophosphates, polyphosphates, and the like.
  • the monophosphate include ammonium salts such as ammonium phosphate, ammonium dihydrogen phosphate, and diammonium hydrogen phosphate; sodium salts such as monosodium phosphate, disodium phosphate, trisodium phosphate, monosodium phosphite, disodium phosphite, and sodium hypophosphite; potassium salts such as monopotassium phosphate, dipotassium phosphate, tripotassium phosphate, monopotassium phosphite, dipotassium phosphite, and potassium hypophosphite; lithium salts such as lithium, dilithium phosphite and lithium hypophosphite; barium salts such as barium dihydrogen phosphate, barium hydrogen phosphate, tribarium phosphate and barium hypophosphit
  • a polyphosphate because the self-extinguishing property of the phosphate-containing flame retardant is improved, and it is more preferable to use ammonium polyphosphate or aluminum phosphite, which forms a foam layer when heated.
  • the phosphate-containing flame retardant may be used alone or in combination of two or more.
  • the content of the phosphate-containing flame retardant is not particularly limited, it is preferably 20 to 50 parts by weight with respect to 100 parts by weight of the polyol compound.
  • Chlorine-Containing Flame Retardant is an element for suppressing the maximum heat release rate at the initial stage of combustion.
  • the following five types of flame retardants are widely used as chlorine-containing flame retardants.
  • TCEP tris(chloroethyl) phosphate
  • TCPP tris( ⁇ -chloropropyl) phosphate
  • TDCP tris(dichloropropyl) phosphate
  • V6 Tetrakis(2-chloroethyl)dichloroisopentyl diphosphate
  • V6 polyoxyalkylene bis (dichloroalkyl) phosphate
  • the content of the chlorine-containing flame retardant is not particularly limited, it is preferably 60 to 120 parts by weight with respect to 100 parts by weight of the polyol compound.
  • Foam stabilizers and surface conditioners that are not included in the formulation in the present invention are described below.
  • the foam stabilizer is an organic siloxane-polyoxyalkylene copolymer or the like used in the production of polyurethane foam.
  • foam stabilizers include L-6900 manufactured by MOMENTIVE, SH-193 manufactured by Dow Corning Toray, and the like.
  • a surface conditioning agent is an additive that functions as an antifoaming agent, a leveling agent, and an anti-popping agent by controlling surface tension to form a good coating film.
  • surface conditioners include acrylic polymers such as SEI-W01 and SEI-1501 manufactured by Kusumoto Kasei.
  • the urethane resin composition according to the present invention may contain the following materials as appropriate.
  • the catalyst used to form the urethane foam is a material that promotes the reaction between isocyanate and active hydrogen present in polyol and the reaction between isocyanate and water.
  • Examples of the catalyst having an amine group include triethylenediamine, N,N,N',N'',N'-pentamethyldiethylenetriamine, N,N,N',N'-tetramethyl-1,6-hexanediamine, N,N,N',N'-tetramethylethylenediamine and other N-alkylpolyalkylenepolyamines, N'-(2-hydroxyethyl)-N,N,N'-trimethylethylenediamine, 1-(2-dimethylaminoethyl)-4-methylpiperazine, 1,2-dimethylimidazole, 1-isobutyl-2-methylimidazole, N-methylmorpholine, N-ethylmorpholine, N,N-dimethylaminoethylmorpholine, dimethylcyclohexylaminedimethylethanolamine, dimethylaminohexanol, dimethylaminoethoxyethanol, diazabicycloundecene and the like
  • catalysts containing organic metals include bismuth octylate, lead octylate, tin(II) 2-ethylhexanoate, dibutylbis[(1-oxooctyl)oxy]stannane, dibutyltin diacetate, and dibutyltin dilaurate.
  • Examples of amine catalyst products include Tosoh's TEDA-L33, TOYOCAT-ET, TOYOCAT-MR, TOYOCAT-TE, TOYOCAT-DT, TOYOCAT-NP, RX-5, RX-10, TOYOCAT-DM70, Evonik's DABCO 33LV, DABCO BL-19, and DABCO BL-1. 1, DABCO DMEA, DABCO T, DABCO N-MM, DABCO N-EM, DABCO XDM, DABCO NC-IM, Polycat201, Polycat204, KAOLIZER NO. 1, KAOLIZER NO. 3, KAOLIZER NO. 10, KAOLIZER NO. 31, KAOLIZER NO.
  • KAOLIZER NO. 22 KAOLIZER NO. 25
  • KAOLIZER NO. 26 KAOLIZER NO. 120
  • KAOLIZER NO. 300 KAOLIZER NO. 350
  • KAOLIZER NO. 390 KAOLIZER NO. 390 and the like.
  • One or more of these catalysts can be used.
  • Foam stabilizer B Silicone foam stabilizer (manufactured by Momentive, product name: L-6900)
  • trimerization catalyst E1 quaternary ammonium salt (manufactured by Evonik, product name: TMR-7)
  • E2 Potassium acetate catalyst (manufactured by Evonik, product name: Polycat46)
  • Foaming agent H1 HFO-1233zd (manufactured by Honeywell, product name: Solstice LBA)
  • H2 HFO-1336mzz (manufactured by Chemours, product name: Opteon 1100)
  • test body preparation method According to the formulations shown in the tables of each figure, the polyol, catalyst, trimerization catalyst, flame retardant, foaming agent, surface conditioner, and foam stabilizer components were weighed into a 1000 mL polypropylene beaker and stirred. This mixture is hereinafter referred to as a polyol premix.
  • the polyol premix and isocyanate were temperature controlled at 5°C.
  • An isocyanate component was added to the temperature-controlled polyol premix component according to the formulation in the table of each figure. After stirring with a hand mixer for about 3 seconds, the mixture was quickly poured into a wooden box of 200 ⁇ 200 ⁇ 200 mm and temperature-controlled at 20° C. to obtain a foam.
  • the isocyanate component is stirred and dispersed in advance immediately before mixing.
  • the foam cured for 24 hours after foaming was cut into a size of 99 mm ⁇ 99 mm ⁇ 50 mm, and after measuring the mass (the foam density was calculated from the obtained mass and size), a corn calorie test body was created. (This specimen is cut to a height of 50 mm in the foaming direction.)
  • Experimental Examples 1 and 2 are formulations containing either a foam stabilizer or a surface conditioner.
  • Test Examples 3, 4, 20, and 21 corresponded to semi-noncombustible materials
  • test specimens according to Experimental Examples 5 to 19 corresponded to noncombustible materials
  • the test specimens according to Experimental Examples 4 to 21 had a foam density of 30 kg/m3 or more.
  • test pieces according to Experimental Examples 23 to 26 and Experimental Examples 29 to 32 were equivalent to noncombustible materials, and had foam densities of 30 kg/m3 or more.

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  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
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  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
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Abstract

Le problème décrit par la présente invention est de fournir une composition de résine d'uréthane qui n'est pas susceptible de gonfler lorsqu'elle est chauffée. La solution selon l'invention est une composition de résine d'uréthane pour former une mousse qui constitue un matériau d'isolation thermique dans un bâtiment, ladite composition de résine d'uréthane contenant au moins un composé polyisocyanate, un composé polyol, un catalyseur de trimérisation, un agent moussant et un agent ignifuge, et ne contenant pas de stabilisateur de mousse ou de conditionneur de surface.
PCT/JP2022/001566 2022-01-18 2022-01-18 Composition de résine d'uréthane WO2023139635A1 (fr)

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JP2020526650A (ja) * 2017-07-11 2020-08-31 ディディピー スペシャリティ エレクトロニック マテリアルズ ユーエス インコーポレーテッド ３成分ポリウレタン接着剤組成物
JP2019094469A (ja) * 2017-11-28 2019-06-20 三菱ケミカル株式会社 難燃性ウレタン樹脂組成物及びその難燃性ポリウレタン成形体
JP2020007386A (ja) * 2018-07-03 2020-01-16 旭有機材株式会社 難燃性ポリウレタンフォーム用発泡性組成物
JP2020033461A (ja) * 2018-08-30 2020-03-05 株式会社日本アクア ウレタン樹脂組成物および建築物の断熱方法
JP2021107515A (ja) * 2019-12-27 2021-07-29 積水化学工業株式会社 ポリオール組成物、発泡性ポリウレタン組成物及びポリウレタンフォーム
WO2021193871A1 (fr) * 2020-03-25 2021-09-30 積水化学工業株式会社 Composition de polyol, composition de polyuréthane et mousse de polyuréthane
KR20210145872A (ko) * 2020-05-25 2021-12-03 대한폴리텍(주) 준불연 단열재 및 이의 제조방법

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