WO2015004928A1 - Composition de résine d'uréthane - Google Patents
Composition de résine d'uréthane Download PDFInfo
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- WO2015004928A1 WO2015004928A1 PCT/JP2014/003705 JP2014003705W WO2015004928A1 WO 2015004928 A1 WO2015004928 A1 WO 2015004928A1 JP 2014003705 W JP2014003705 W JP 2014003705W WO 2015004928 A1 WO2015004928 A1 WO 2015004928A1
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- urethane resin
- weight
- parts
- resin composition
- flame retardant
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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
- 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
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4205—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups
- C08G18/4208—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing aromatic groups
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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
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/09—Processes comprising oligomerisation of isocyanates or isothiocyanates involving reaction of a part of the isocyanate or isothiocyanate groups with each other in the reaction mixture
- C08G18/092—Processes comprising oligomerisation of isocyanates or isothiocyanates involving reaction of a part of the isocyanate or isothiocyanate groups with each other in the reaction mixture oligomerisation to isocyanurate groups
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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
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/161—Catalysts containing two or more components to be covered by at least two of the groups C08G18/166, C08G18/18 or C08G18/22
- C08G18/163—Catalysts containing two or more components to be covered by at least two of the groups C08G18/166, C08G18/18 or C08G18/22 covered by C08G18/18 and C08G18/22
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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
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
- C08G18/1808—Catalysts containing secondary or tertiary amines or salts thereof having alkylene polyamine groups
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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
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/22—Catalysts containing metal compounds
- C08G18/225—Catalysts containing metal compounds of alkali or alkaline earth metals
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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
- 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
- C08G18/48—Polyethers
- C08G18/4829—Polyethers containing at least three hydroxy groups
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/0095—Mixtures of at least two compounding ingredients belonging to different one-dot groups
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/04—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent
- C08J9/12—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent
- C08J9/14—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent organic
- C08J9/143—Halogen containing compounds
- C08J9/144—Halogen containing compounds containing carbon, halogen and hydrogen only
- C08J9/146—Halogen containing compounds containing carbon, halogen and hydrogen only only fluorine as halogen atoms
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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
- C08G2110/00—Foam properties
- C08G2110/0025—Foam properties rigid
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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
- C08G2110/00—Foam properties
- C08G2110/0041—Foam properties having specified density
- C08G2110/005—< 50kg/m3
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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
- C08G2110/00—Foam properties
- C08G2110/0083—Foam properties prepared using water as the sole blowing agent
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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
- C08G2115/00—Oligomerisation
- C08G2115/02—Oligomerisation to isocyanurate groups
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
- C08J2375/04—Polyurethanes
- C08J2375/06—Polyurethanes from polyesters
Definitions
- the present invention relates to a urethane resin composition.
- Concrete reinforced with reinforcing bars or the like is used for apartment houses such as condominiums, detached houses, various facilities of schools, and outer walls of commercial buildings. Concrete has the advantage of maintaining strength over a long period of time as a structural material.
- hot weather such as summer
- heat is accumulated in concrete due to outside air or direct sunlight, and the inside of the building is heated by the accumulated heat.
- the concrete is cooled not only in summer but also in cold periods such as winter. As a result, the interior of the building is cooled. In this way, the outside temperature may affect the inside of the building for a long time through the concrete. In order to reduce this effect, heat insulation is usually applied to concrete.
- a hard urethane foam is sprayed on the concrete surface to form a heat insulating layer.
- the hard urethane foam may burn if a fire or the like occurs inside the building.
- a fire-resistant material called white cement which is mainly composed of volcanic ash, cement or the like, is sprayed on the surface of the hard urethane foam. By using the white cement, it is possible to prevent the hard urethane foam from burning.
- a technique for improving the flame retardancy of a cured urethane resin composition by forming a nurate bond when the urethane resin composition is cured is disclosed (patent) Reference 1).
- the technique which improves the flame retardance of a urethane resin composition is disclosed by using ammonium polyphosphate and red phosphorus as a flame retardant (patent document 2).
- a technique for improving the flame retardancy of a urethane resin composition by using a catalyst that promotes trimerization of ammonium polyphosphate and isocyanate groups as a flame retardant is also disclosed (Patent Document 3).
- An object of the present invention is to provide a urethane resin composition having a small calorific value when burned and excellent in flame retardancy.
- a urethane resin composition comprising a urethane resin containing a polyisocyanate compound and a polyol compound, a flame retardant, and a trimerization catalyst for promoting a trimerization reaction of an isocyanate group contained in the polyisocyanate compound,
- the flame retardant comprises red phosphorus and a phosphate-containing flame retardant;
- the red phosphorus is in the range of 3.0 to 20 parts by weight and the phosphate-containing flame retardant is in the range of 1.0 to 18 parts by weight with respect to 100 parts by weight of the urethane resin.
- the present invention provides a urethane resin composition.
- One of the present invention is [2] The urethane resin composition according to the above [1], wherein the weight ratio between the red phosphorus and the phosphate-containing flame retardant is in the range of 1: 3 to 3: 1.
- One of the present invention is [3] The urethane resin composition according to the above [1] or [2], wherein the phosphate-containing flame retardant is a monophosphate.
- One of the present invention is [4] The urethane resin composition according to any one of the above [1] to [3], wherein the polyisocyanate compound and the polyol compound contained in the urethane resin have an index in the range of 150 to 700. is there.
- One of the present invention is [5] The urethane resin composition according to any one of the above [1] to [4], wherein the urethane resin composition contains at least one of a foam stabilizer and a foaming agent.
- One of the present invention is [6] The urethane resin composition according to any one of the above [1] to [5], wherein the density after curing is in the range of 0.020 to 0.080 kg / m 3 .
- the present invention also provides [7] A molded product obtained by molding the urethane resin composition according to any one of [1] to [6] is provided.
- the present invention also provides [8] The molded body according to the above [7], wherein the molded body is used for a building, an automobile, a railway vehicle, a ship, or an airplane.
- the urethane resin composition according to the present invention is excellent in handleability. Moreover, since the molded object obtained by the urethane resin composition which concerns on this invention has little calorific value at the time of combustion, it can exhibit the outstanding flame retardance.
- the urethane resin composition according to the present invention will be described.
- the urethane resin used for the urethane resin composition will be described.
- the polyisocyanate compound as a main ingredient what contains the polyisocyanate compound as a main ingredient, the polyol compound as a hardening
- the polyisocyanate compound that is the main component of the urethane resin include aromatic polyisocyanates, alicyclic polyisocyanates, and aliphatic polyisocyanates.
- aromatic polyisocyanate examples include phenylene diisocyanate, tolylene diisocyanate, xylylene diisocyanate, diphenylmethane diisocyanate, dimethyldiphenylmethane diisocyanate, triphenylmethane triisocyanate, naphthalene diisocyanate, polymethylene polyphenyl polyisocyanate, and the like.
- alicyclic polyisocyanate examples include cyclohexylene diisocyanate, methylcyclohexylene diisocyanate, isophorone diisocyanate, dicyclohexylmethane diisocyanate, and dimethyldicyclohexylmethane diisocyanate.
- Examples of the aliphatic polyisocyanate include methylene diisocyanate, ethylene diisocyanate, propylene diisocyanate, tetramethylene diisocyanate, and hexamethylene diisocyanate.
- the said polyisocyanate compound can use 1 type, or 2 or more types.
- the main component of the urethane resin is preferably diphenylmethane diisocyanate for reasons such as ease of use and availability.
- polyol compound that is a curing agent for the urethane resin examples include polylactone polyol, polycarbonate polyol, aromatic polyol, alicyclic polyol, aliphatic polyol, polyester polyol, polymer polyol, and polyether polyol.
- polylactone polyol examples include polypropiolactone glycol, polycaprolactone glycol, and polyvalerolactone glycol.
- the polycarbonate polyol can be obtained, for example, by a dealcoholization reaction between a hydroxyl group-containing compound such as ethylene glycol, propylene glycol, butanediol, pentanediol, hexanediol, octanediol, or nonanediol, and diethylene carbonate, dipropylene carbonate, or the like.
- a hydroxyl group-containing compound such as ethylene glycol, propylene glycol, butanediol, pentanediol, hexanediol, octanediol, or nonanediol, and diethylene carbonate, dipropylene carbonate, or the like.
- Examples of the aromatic polyol include bisphenol A, bisphenol F, phenol novolak, and cresol novolak.
- Examples of the alicyclic polyol include cyclohexanediol, methylcyclohexanediol, isophoronediol, dicyclohexylmethanediol, dimethyldicyclohexylmethanediol, and the like.
- Examples of the aliphatic polyol include ethylene glycol, propylene glycol, butanediol, pentanediol, and hexanediol.
- polyester polyol examples include a polymer obtained by dehydration condensation of a polybasic acid and a polyhydric alcohol, and a polymer obtained by ring-opening polymerization of a lactone such as ⁇ -caprolactone and ⁇ -methyl- ⁇ -caprolactone. And a condensate of hydroxycarboxylic acid and the above polyhydric alcohol.
- polybasic acid examples include adipic acid, azelaic acid, sebacic acid, terephthalic acid, isophthalic acid, and succinic acid.
- polyhydric alcohol examples include bisphenol A, ethylene glycol, 1,2-propylene glycol, 1,4-butanediol, diethylene glycol, 1,6-hexane glycol, neopentyl glycol, and the like. It is done.
- hydroxycarboxylic acid examples include castor oil, a reaction product of castor oil and ethylene glycol, and the like.
- polymer polyol examples include a polymer obtained by graft polymerization of an ethylenically unsaturated compound such as acrylonitrile, styrene, methyl acrylate, and methacrylate on the aromatic polyol, alicyclic polyol, aliphatic polyol, polyester polyol, and the like. , Polybutadiene polyols, modified polyols of polyhydric alcohols, or hydrogenated products thereof.
- modified polyol of the polyhydric alcohol examples include those modified by reacting a raw material polyhydric alcohol with an alkylene oxide.
- the polyhydric alcohol include trihydric alcohols such as glycerin and trimethylolpropane, Pentaerythritol, sorbitol, mannitol, sorbitan, diglycerin, dipentaerythritol, etc., tetra- to octavalent alcohols such as sucrose, glucose, mannose, fructose, methyl glucoside and derivatives thereof, Phenol, phloroglucin, cresol, pyrogallol, catechol, hydroquinone, bisphenol A, bisphenol F, bisphenol S, 1-hydroxynaphthalene, 1,3,6,8-tetrahydroxynaphthalene, anthrol, 1,4,5 , 8-tetrahydroxyanthracene, phenols such as 1-hydroxypyrene, Polybutadiene polyol,
- the method for modifying the polyhydric alcohol is not particularly limited, but a method of adding alkylene oxide (hereinafter abbreviated as “AO”) is preferably used.
- the AO include AO having 2 to 6 carbon atoms, such as ethylene oxide (hereinafter abbreviated as “EO”), 1,2-propylene oxide (hereinafter abbreviated as “PO”), 1,3-propyloxide. 1,2-butylene oxide, 1,4-butylene oxide and the like.
- EO ethylene oxide
- PO 1,2-propylene oxide
- 1,3-propyloxide 1,2-butylene oxide, 1,4-butylene oxide and the like.
- PO, EO, and 1,2-butylene oxide are preferable from the viewpoint of properties and reactivity, and PO and EO are more preferable.
- block addition or random addition may be used, or a combination thereof may be used.
- polyether polyol examples include ring-opening polymerization of at least one alkylene oxide such as ethylene oxide, propylene oxide, and tetrahydrofuran in the presence of at least one low molecular weight active hydrogen compound having two or more active hydrogens. And the resulting polymer.
- the low molecular weight active hydrogen compound having two or more active hydrogens include diols such as bisphenol A, ethylene glycol, propylene glycol, butylene glycol, 1,6-hexanediol, Triols such as glycerin and trimethylolpropane, Examples include amines such as ethylenediamine and butylenediamine.
- the polyol used in the present invention is preferably a polyester polyol or a polyether polyol because the effect of reducing the total calorific value upon combustion is great. Among them, it is more preferable to use a polyester polyol having a molecular weight of 300 to 500.
- the index which is the ratio (NCO / OH) of the active hydrogen group (OH) of the polyol compound and water to the active isocyanate group (NCO) in the polyisocyanate compound is [equivalent number of isocyanate] ⁇ 100 ⁇ [ The number of equivalents of polyol + the number of equivalents of water].
- the equivalent number of the polyol compound is represented by [hydroxyl value of polyol compound (mgKOH / g)] ⁇ [weight of polyol compound (g)] ⁇ [molecular weight of potassium hydroxide].
- the equivalent number of the isocyanate compound is represented by [molecular weight of isocyanate group] ⁇ 100 ⁇ [weight% of isocyanate group].
- the equivalent number of water is represented by [weight of water (g)] ⁇ 2 ⁇ [molecular weight of water].
- the index range is usually mixed so as to be in the range of 150-700. This range is preferably in the range of 200 to 700, more preferably in the range of 300 to 700, and still more preferably in the range of 350 to 650.
- the equivalent ratio is 150 or more, the amount of isocyanurate groups in the urethane resin composition can be prevented from decreasing, and thus the flame retardancy can be prevented from being decreased.
- the equivalent ratio is 700 or less, the urethane resin composition can be prevented from becoming too brittle. be able to.
- a urethane resin curing catalyst can be used in addition to the urethane resin.
- the urethane curing catalyst include amino compounds, tin compounds, and acetylacetone metal salts.
- amino compound examples include pentamethyldiethylenetriamine, triethylamine, N-methylmorpholine bis (2-dimethylaminoethyl) ether, N, N, N ′, N ′′, N ′′ -pentamethyldiethylenetriamine, N, N, N '-Trimethylaminoethyl-ethanolamine, bis (2-dimethylaminoethyl) ether, N-methyl-N'N'-dimethylaminoethylpiperazine, imidazole substituted secondary amine functional group in imidazole ring with cyanoethyl group
- N, N-dimethylcyclohexylamine, diazabicycloundecene triethylenediamine, tetramethylhexamethylenediamine, N-methylimidazole, trimethylaminoethylpiperazine, tripropylamine, Examples thereof include tetramethylammonium salt, tetraeth
- tin compound examples include dibutyltin diacetate and dibutyltin dilaurate.
- acetylacetone metal salt examples include acetylacetone aluminum, acetylacetone iron, acetylacetone copper, acetylacetone zinc, acetylacetone beryllium, acetylacetone chromium, acetylacetone indium, acetylacetone manganese, acetylacetone molybdenum, acetylacetone titanium, acetylacetone cobalt, acetylacetone vanadium, and acetylacetone zirconium. It is done.
- the urethane resin curing catalyst can be used alone or in combination of two or more.
- the addition amount of the urethane resin curing catalyst used in the urethane resin composition according to the present invention is not particularly limited, but is preferably in the range of 0.01 to 10 parts by weight with respect to 100 parts by weight of the urethane resin. More preferably, it is in the range of 0.01 to 8 parts by weight, more preferably in the range of 0.01 to 6 parts by weight, and in the range of 0.01 to 1.5 parts by weight. Most preferably. In the case of 0.01 parts by weight or more and 10 parts by weight or less, it is easy to handle and the reaction is easily controlled.
- the polyurethane resin used in the present invention may be a polyurethane resin that has reacted with an isocyanate group contained in a polyisocyanate compound, which is the main component of the polyurethane resin, to trimerize it and promote the formation of an isocyanurate ring.
- Aromatic compounds such as S-triazine, potassium acetate, sodium acetate, potassium 2-ethylhexanoate, sodium 2-ethylhexanoate, quaternary ammonium compounds such as tertiary amine carboxylates, 2-ethylaziridine, etc.
- Amine compounds such as aziridines, lead compounds such as diazabicycloundecene, lead naphthenate and lead octylate, alcoholate compounds such as sodium methoxide, phenolate compounds such as potassium phenoxide, quaternary ammonium salts of carboxylic acids, etc. Use it.
- the addition amount of the trimerization catalyst used in the flame-retardant urethane resin composition according to the present invention is not particularly limited, but may be in the range of 0.01 to 10 parts by weight with respect to 100 parts by weight of the urethane resin. Preferably, it is in the range of 0.01 to 8 parts by weight, more preferably in the range of 0.01 to 6 parts by weight, and 0.5 to 1.5 parts by weight. The range is most preferable.
- the amount is 0.01 parts by weight or more, the amount of isocyanurate groups in the urethane resin composition can be prevented from decreasing, so that the flame retardancy can be prevented.
- the amount is 10 parts by weight or less, the urethane resin composition Can be prevented from becoming too brittle.
- the trimerization catalyst can be used alone or in combination of two or more.
- a foaming agent is used in addition to the urethane resin.
- a foaming agent can be added to the urethane resin composition according to the present invention.
- foaming agent examples include water, Low boiling point hydrocarbons such as propane, butane, pentane, hexane, heptane, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, Chlorinated aliphatic hydrocarbon compounds such as dichloroethane, propyl chloride, isopropyl chloride, butyl chloride, isobutyl chloride, pentyl chloride, isopentyl chloride, Fluorine compounds such as trichloromonofluoromethane, trichlorotrifluoroethane, CHF 3 , CH 2 F 2 , CH 3 F, Hydrochlorofluorocarbon compounds such as dichloromonofluoroethane (for example, HCFC141b (1,1-dichloro-1-fluoroethane), HCFC22 (chlorodifluoromethane), HCFC142
- the foaming agent used in the present invention is preferably pentane, hydrofluorocarbon, or water, and more preferably hydrofluorocarbon and water are used in combination or water is used alone.
- the amount of the foaming agent used in the urethane resin composition according to the present invention is not particularly limited, but is preferably in the range of 0.1 to 20 parts by weight with respect to 100 parts by weight of the urethane resin. More preferably, it is in the range of 1 to 18 parts by weight, more preferably in the range of 0.1 to 15 parts by weight, and in the range of 0.3 to 10 parts by weight. Most preferred.
- the water range is 0.1 parts by weight or more, formation of bubbles is promoted and a good foam is obtained, and when it is 20 parts by weight or less, the vaporization force is increased and the bubbles are prevented from becoming coarse. Can do.
- a foam stabilizer can also be used in the urethane resin composition according to the present invention.
- the foam stabilizer include surfactants such as polyoxyalkylene foam stabilizers such as polyoxyalkylene alkyl ether, silicone foam stabilizers such as organopolysiloxane, and the like.
- the amount of the foam stabilizer used for the urethane resin cured by the chemical reaction is appropriately set according to the urethane resin cured by the chemical reaction to be used. For example, for example, 100 parts by weight of the urethane resin On the other hand, it is preferably 0.01 to 5 parts by weight, more preferably 0.1 to 4 parts by weight, and still more preferably 1 to 3 parts by weight.
- the catalyst, the foaming agent and the foam stabilizer may be used alone or in combination of two or more.
- red phosphorus used in the present invention will be described.
- a commercial item can be selected suitably and can be used.
- the amount of red phosphorus used in the fireproof urethane resin composition according to the present invention is in the range of 3.0 to 20 parts by weight with respect to 100 parts by weight of the urethane resin. This range is more preferably in the range of 3.0 to 12 parts by weight.
- the range of the red phosphorus is 3.0 parts by weight or more, the self-extinguishing property of the urethane resin composition according to the present invention is maintained, and when it is 20 parts by weight or less, the urethane resin composition according to the present invention Foaming is not hindered.
- the phosphate-containing flame retardant used in the present invention contains phosphoric acid.
- phosphoric acid used in the phosphate-containing flame retardant include various phosphoric acids such as monophosphoric acid, pyrophosphoric acid, and polyphosphoric acid.
- Examples of the phosphate-containing flame retardant include salts of the various phosphoric acids with at least one metal or compound selected from metals of Group IA to IVB of the periodic table, ammonia, aliphatic amines, and aromatic amines. Can be mentioned.
- Examples of the metals in 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, piperazine and the like.
- Examples of the aromatic amine include pyridine, triazine, melamine, and ammonium.
- the phosphate-containing flame retardant may be subjected to a known water resistance improving treatment such as silane coupling agent treatment or coating with a melamine resin, and a known foaming aid such as melamine or pentaerythritol may be added. May be.
- phosphate-containing flame retardant examples include monophosphate, pyrophosphate and the like.
- the monophosphate is not particularly limited, and examples thereof include ammonium salts such as ammonium dihydrogen phosphate and diammonium hydrogen phosphate.
- Sodium salts such as monosodium phosphate, disodium phosphate, trisodium phosphate, monosodium phosphite, disodium phosphite, sodium hypophosphite, Potassium salts such as monopotassium phosphate, dipotassium phosphate, tripotassium phosphate, monopotassium phosphite, dipotassium phosphite, potassium hypophosphite, Lithium salts such as monolithium phosphate, dilithium phosphate, trilithium phosphate, monolithium phosphite, dilithium phosphite, lithium hypophosphite, Barium salts such as barium dihydrogen phosphate, barium hydrogen phosphate, tribarium phosphate, barium hypophosphite
- a monophosphate such as ammonium dihydrogen phosphate, diammonium hydrogen phosphate, primary aluminum phosphate, phosphoric acid It is more preferable to use at least one selected from the group consisting of monosodium and tertiary aluminum phosphate, and it is more preferable to use ammonium dihydrogen phosphate and diammonium hydrogen phosphate.
- the phosphate-containing flame retardant can be used alone or in combination of two or more.
- the amount of the phosphate-containing flame retardant used in the present invention is in the range of 1.0 to 18 parts by weight with respect to 100 parts by weight of the urethane resin.
- the range of the phosphate-containing flame retardant is 1.0 part by weight or more, the self-extinguishing property of the urethane resin composition according to the present invention is maintained, and when it is 18 parts by weight or less, the urethane according to the present invention is maintained. Foaming of the resin composition is not inhibited.
- the red phosphorus and the phosphate-containing flame retardant are used together because the total calorific value of the molded article of the urethane resin composition obtained is reduced.
- the weight ratio of the red phosphorus and the phosphate-containing flame retardant is preferably in the range of 1: 3 to 3: 1. .
- the urethane resin composition according to the present invention can be used in combination with a flame retardant other than the red phosphorus and the phosphate-containing flame retardant.
- flame retardants include phosphate esters, bromine-containing flame retardants, boron-containing flame retardants, and antimony-containing flame retardants.
- the phosphate ester is not particularly limited, but it is preferable to use a monophosphate ester, a condensed phosphate ester, or the like.
- the monophosphate ester is not particularly limited, and examples thereof include trimethyl phosphate, triethyl phosphate, tributyl phosphate, tri (2-ethylhexyl) phosphate, tributoxyethyl phosphate, triphenyl phosphate, tricresyl phosphate, and trixylenyl phosphate.
- the condensed phosphate ester is not particularly limited, and examples thereof include trialkyl polyphosphate, resorcinol polyphenyl phosphate, resorcinol poly (di-2,6-xylyl) phosphate (trade name PX- manufactured by Daihachi Chemical Industry Co., Ltd.). 200), hydroquinone poly (2,6-xylyl) phosphate and condensed phosphates such as condensates thereof.
- condensed phosphate esters examples include resorcinol polyphenyl phosphate (trade name CR-733S), bisphenol A polycresyl phosphate (trade name CR-741), aromatic condensed phosphate ester (trade name CR747), and resorcinol.
- examples thereof include polyphenyl phosphate (trade name ADK STAB PFR, manufactured by ADEKA), and bisphenol A polycresyl phosphate (trade names FP-600 and FP-700).
- a monophosphate ester because it is highly effective in reducing the viscosity in the composition before curing and reducing the initial calorific value, and using tris ( ⁇ -chloropropyl) phosphate. Is more preferable.
- the phosphoric acid ester can be used alone or in combination of two or more.
- the addition amount of the phosphate ester used in the present invention is in the range of 0.1 to 200 parts by weight with respect to 100 parts by weight of the urethane resin.
- the amount of the phosphate ester added is preferably in the range of 0.1 to 100 parts by weight, more preferably in the range of 0.1 to 50 parts by weight, and 5 to 15 parts by weight. If it is the range, it is still more preferable.
- the range of the phosphoric acid ester is 0.1 parts by weight or more, the molded body made of the urethane resin composition according to the present invention can be prevented from cracking the dense residue formed by the heat of fire, and 200 parts by weight or less. In this case, foaming of the urethane resin composition according to the present invention is not inhibited.
- the bromine-containing flame retardant is not particularly limited as long as it is a compound containing bromine in the molecular structure, and examples thereof include aromatic brominated compounds.
- aromatic brominated compounds include, for example, hexabromobenzene, pentabromotoluene, hexabromobiphenyl, decabromobiphenyl, hexabromocyclodecane, decabromodiphenyl ether, octabromodiphenyl ether, hexabromodiphenyl ether, bis (penta Monomer organic bromine compounds such as bromophenoxy) ethane, ethylene-bis (tetrabromophthalimide), tetrabromobisphenol A, A polycarbonate oligomer produced from brominated bisphenol A as a raw material, a brominated polycarbonate such as a copolymer of the polycarbonate oligomer and bisphenol A, Brominated epoxy compounds such as
- the bromine-containing flame retardant can be used alone or in combination of two or more.
- the amount of the bromine-containing flame retardant used in the present invention is not particularly limited, but is preferably in the range of 0.1 to 60 parts by weight with respect to 100 parts by weight of the urethane resin, and 0.1 parts by weight.
- the range is more preferably in the range of ⁇ 50 parts by weight, still more preferably in the range of 0.1 part by weight to 40 parts by weight, and most preferably in the range of 2 parts by weight to 5 parts by weight.
- Examples of the boron-containing flame retardant used in the present invention include borax, boron oxide, boric acid, and borate.
- Examples of the boron oxide include diboron trioxide, boron trioxide, diboron dioxide, tetraboron trioxide, and tetraboron pentoxide.
- Examples of the borate include alkali metals, alkaline earth metals, elements of Group 4, Group 12, and Group 13 of the periodic table, and ammonium borate.
- alkali metal borate such as lithium borate, sodium borate, potassium borate, cesium borate
- alkaline earth metal borate such as magnesium borate, calcium borate, barium borate, boron
- zirconium acid zinc borate, aluminum borate, and ammonium borate.
- the boron-containing flame retardant used in the present invention is preferably a borate, more preferably zinc borate.
- the boron-containing flame retardant can be used alone or in combination of two or more.
- the amount of boron-containing flame retardant used in the present invention is in the range of 0.1 to 60 parts by weight with respect to 100 parts by weight of the urethane resin.
- the amount of boron-containing flame retardant added is preferably in the range of 0.1 to 50 parts by weight, more preferably in the range of 0.1 to 40 parts by weight, and 1 to 10 parts by weight. More preferably, it is in the range of parts.
- the range of the boron-containing flame retardant is 0.1 parts by weight or more, the self-extinguishing property of the urethane resin composition according to the present invention is maintained, and when it is 60 parts by weight or less, the urethane resin composition according to the present invention.
- the foaming of objects is not hindered.
- antimony-containing flame retardant examples include antimony oxide, antimonate, and pyroantimonate.
- antimony oxide examples include antimony trioxide and antimony pentoxide.
- antimonate examples include sodium antimonate and potassium antimonate.
- pyroantimonate examples include sodium pyroantimonate and potassium pyroantimonate.
- the antimony-containing flame retardant used in the present invention is preferably antimony trioxide.
- the antimony-containing flame retardant can be used alone or in combination of two or more.
- the amount of the antimony-containing flame retardant added is not particularly limited, but is preferably in the range of 0.1 to 60 parts by weight, preferably 0.1 to 50 parts by weight with respect to 100 parts by weight of the urethane resin. More preferred is a range of 0.1 parts by weight to 40 parts by weight, still more preferred is a range of 1 part by weight to 10 parts by weight.
- the range of the antimony-containing flame retardant is 0.1 parts by weight or more, the self-extinguishing property of the urethane resin composition according to the present invention is maintained, and when it is 60 parts by weight or less, the urethane resin composition according to the present invention.
- the foaming of objects is not hindered.
- the urethane resin composition according to the present invention can use an inorganic filler.
- the inorganic filler is not particularly limited.
- the inorganic filler can be used alone or in combination of two or more.
- the urethane resin composition according to the present invention is an antioxidant, such as phenol-containing, amine-containing, sulfur-containing, heat stabilizer, metal harm-preventing agent, as long as the object of the present invention is not impaired.
- An antistatic agent, a stabilizer, a crosslinking agent, a lubricant, a softener, a pigment, an additive such as a tackifier resin, and a tackifier such as polybutene and a petroleum resin can be included.
- the urethane resin composition according to the present invention reacts and cures, the viscosity changes with time. Therefore, before using the urethane resin composition according to the present invention, the urethane resin composition is divided into two or more to prevent the urethane resin composition from reacting and curing. And when using the urethane resin composition which concerns on this invention, the urethane resin composition which concerns on this invention is obtained by putting together the said urethane resin composition divided
- the method for producing the urethane resin composition is not particularly limited.
- the method of mixing the components of the urethane resin composition, the urethane resin composition is suspended in an organic solvent, or heated and melted.
- a method of preparing a slurry by dispersing in a solvent, or a reaction curable resin component contained in the urethane resin composition contains a component that is solid at a temperature of 25 ° C.
- the urethane resin composition can be obtained by a method such as melting the urethane resin composition under heating.
- the main component of urethane resin and the curing agent may be separately kneaded together with a filler or the like and kneaded with a static mixer, a dynamic mixer or the like immediately before injection. Further, the components of the urethane resin composition excluding the catalyst and the catalyst can be kneaded in the same manner immediately before injection.
- the urethane resin composition according to the present invention can be obtained by the method described above.
- a method for curing the urethane resin composition according to the present invention will be described.
- the reaction starts, the viscosity increases with the passage of time, and the fluidity is lost.
- a molded body made of the urethane resin composition can be obtained by injecting the urethane resin composition into a container such as a mold or a frame material and curing it.
- heat can be applied or pressure can be applied.
- the density of the urethane resin composition after curing is not particularly limited, but is preferably in the range of 0.020 to 0.080 kg / m 3 , and preferably in the range of 0.030 to 0.080 kg / m 3. , still more preferably in the range of 0.030 ⁇ 0.070kg / m 3, and most preferred range of 0.030 ⁇ 0.060kg / m 3.
- the molded body made of the urethane resin composition after curing is easy to handle because of its low specific gravity.
- a molded body made of the urethane resin composition is cut into a length of 10 cm, a width of 10 cm and a thickness of 5 cm to prepare a sample for a corn calorimeter test.
- the total calorific value of the corn calorimeter test when heated at a radiant heat intensity of 50 kW / m 2 for 20 minutes can be measured in accordance with the test method of ISO-5660. it can.
- the urethane resin composition according to Example 1 was prepared by being divided into three components (A) to (C).
- the details of each component shown in Table 1 are as follows.
- B-4 Trimerization catalyst (manufactured by Kao Corporation, product name: Kao Riser No. 410)
- B-5 Trimerization catalyst (manufactured by Kao Corporation, product name: Kao Riser No. 420)
- B-6 Pentamethyldiethylenetriamine (manufactured by Tosoh Corporation, product name: TOYOCAT-DT)
- C-1 Water C-2: HFC-365mfc (1,1,1,3,3-pentafluorobutane, manufactured by Solvay Japan) using the following mixture HFC-245fa (1,1,1,3,3-pentafluoropropane, manufactured by Central Glass Co., Ltd.)
- Component (X) polyisocyanate compound (hereinafter referred to as “polyisocyanate”) MDI (manufactured by Nippon Polyurethane Industry Co., Ltd., product name: Millionate MR-200) Viscosity: 167 mPa ⁇ s, isocyanate content 30.5-32.0%
- each component of a polyol compound, a catalyst, a flame retardant and a polyisocyanate is weighed in a 1000 ml polypropylene beaker, using a three-one motor (product name: BLW1200), 25 ° C., 400 rpm. The mixture was stirred for 2 minutes. A foam stabilizer and a foaming agent were added to the above components after stirring, and the mixture was stirred for about 10 seconds at 25 ° C. and 1200 rpm using a three-one motor to prepare a foam.
- each compounding component shown in Table 1 is a unit by weight, and the total value of the polyol compound and the polyisocyanate is expressed as 100 parts by weight.
- the obtained urethane resin composition lost fluidity with the passage of time, and a cured product of the urethane resin composition was obtained.
- the cured product was evaluated according to the following criteria, and the results are shown in Table 1. The density was 0.052. The results are also shown in Table 1 (unit: g / cm 3 ).
- Example 1 Compared to Example 1, the amount of foaming agent C-1 used was 0.6 parts by weight, except that D-3 was used in an amount of 3.0 parts by weight instead of flame retardant D-2. The experiment was conducted exactly as in Example 1. The results are shown in Table 1.
- Example 1 Compared to Example 1, the amount of foaming agent C-1 used was 0.6 parts by weight, except that D-4 was used in place of flame retardant D-2. The experiment was conducted exactly as in Example 1. The results are shown in Table 1.
- Example 1 Compared to Example 1, the amount of foaming agent C-1 used was 0.6 parts by weight, except that D-5 was used in an amount of 3.0 parts by weight instead of flame retardant D-2. The experiment was conducted exactly as in Example 1. The results are shown in Table 1.
- Example 1 Compared to the case of Example 1, the amount of foaming agent C-1 used was 0.6 parts by weight, except that D-6 was used in place of flame retardant D-2. The experiment was conducted exactly as in Example 1. The results are shown in Table 1.
- Example 1 Compared to the case of Example 1, the amount of foaming agent C-1 used was 1.0 part by weight, the foaming agent C-2 was not used, and the amount of polyol A-1 used was 11. The experiment was performed in the same manner as in Example 1 except that the amount was 9 parts by weight and that the amount of polyisocyanate used was 88.1 parts by weight. The results are shown in Table 1.
- Example 6 The experiment was performed in the same manner as in Example 6 except that 6.0 parts by weight of flame retardant D-2 was used as compared with Example 6. The results are shown in Table 1.
- Example 1 Compared to the case of Example 1, the amount of foaming agent C-1 used was 0.6 parts by weight, the amount of flame retardant D-2 used was 6.0 parts by weight, polyol compound A- The experiment was performed in exactly the same manner as in Example 1, except that 15.4 parts by weight of polyol compound A-2 was used instead of 1, and the amount of polyisocyanate used was 84.6 parts by weight. The results are shown in Table 1.
- Example 8 Compared with the case of Example 8, it was carried out except that 30.1 parts by weight of polyol compound A-3 was used instead of polyol compound A-2, and that the amount of polyisocyanate used was 69.9 parts by weight. The experiment was conducted exactly as in Example 8. The results are shown in Table 1.
- Example 8 Compared to the case of Example 8, it was carried out except that 15.5 parts by weight of polyol compound A-4 was used instead of polyol compound A-2 and that the amount of polyisocyanate used was 84.5 parts by weight. The experiment was conducted exactly as in Example 8. The results are shown in Table 1.
- Example 8 Compared to the case of Example 8, it was carried out except that 16.7 parts by weight of polyol compound A-5 was used instead of polyol compound A-2, and the amount of polyisocyanate used was 83.3 parts by weight. The experiment was conducted exactly as in Example 8. The results are shown in Table 1.
- Example 1 Compared to the case of Example 1, 0.7 parts by weight of the trimerization catalyst B-3 was used instead of the trimerization catalyst B-2, and the use amount of the blowing agent C-1 was 0.6 parts by weight. The experiment was performed in exactly the same manner as in Example 1 except that. The results are shown in Table 1.
- Example 12 As compared with Example 12, the experiment was performed in exactly the same manner as in Example 12 except that 0.7 parts by weight of trimerization catalyst B-5 was used instead of trimerization catalyst B-3. The results are shown in Table 1.
- Example 2 In the case of Example 1, except that the amount of the flame retardant D-1 used was 12.0 parts by weight and the amount of the flame retardant D-2 used was 6.0 parts by weight as compared with the case of Example 1. The experiment was carried out in exactly the same way. The results are shown in Table 2.
- Example 2 In the case of Example 1, except that the amount of the flame retardant D-1 used was 3.0 parts by weight and the amount of the flame retardant D-2 used was 1.0 parts by weight, compared with the case of Example 1. The experiment was carried out in exactly the same way. The results are shown in Table 2.
- Example 2 The experiment was performed in exactly the same manner as in Example 1, except that the amount of flame retardant D-1 used was 9.0 parts by weight compared to Example 1. The results are shown in Table 2.
- Example 2 In the case of Example 1 except that the amount of the flame retardant D-1 used was 3.0 parts by weight and the amount of the flame retardant D-2 used was 9.0 parts by weight compared to the case of Example 1. The experiment was carried out in exactly the same way. The results are shown in Table 2.
- Example 2 In the case of Example 1 except that the amount of the flame retardant D-1 used was 18.0 parts by weight and the amount of the flame retardant D-2 used was 6.0 parts by weight compared to the case of Example 1. The experiment was carried out in exactly the same way. The results are shown in Table 2.
- Example 2 The experiment was performed in exactly the same manner as in Example 1, except that the amount of flame retardant D-2 used was 18.0 parts by weight compared to Example 1. The results are shown in Table 2.
- Example 2 Compared to Example 1, the amount of polyol compound A-1 used was 10.0 parts by weight, and the amount of polyisocyanate used was 90.0 parts by weight. The experiment was performed in the same manner as in Example 1 except that the amount of flame retardant D-1 used was 3.0 parts by weight and the amount of flame retardant D-2 used was 1.0 parts by weight. The results are shown in Table 2.
- Example 22 In the case of Example 22, except that the amount of the flame retardant D-1 used was 1.0 part by weight and the amount of the flame retardant D-2 used was 3.0 parts by weight as compared with the case of Example 22. The experiment was carried out in exactly the same way. The results are shown in Table 2.
- Example 22 In the case of Example 22, except that the amount of the flame retardant D-1 used was 9.0 parts by weight and the amount of the flame retardant D-2 used was 3.0 parts by weight, compared with the case of Example 22. The experiment was carried out in exactly the same way. The results are shown in Table 2.
- Example 22 The experiment was performed in exactly the same manner as in Example 22, except that the amount of flame retardant D-2 used was 9.0 parts by weight, compared with Example 22. The results are shown in Table 2.
- Example 22 In the case of Example 22, except that the amount of the flame retardant D-1 used was 18.0 parts by weight and the amount of the flame retardant D-2 used was 6.0 parts by weight, compared with the case of Example 22. The experiment was carried out in exactly the same way. The results are shown in Table 2.
- Example 22 The experiment was performed in exactly the same manner as in Example 22, except that the amount of flame retardant D-2 used was 18.0 parts by weight, compared with Example 22. The results are shown in Table 2. The results are shown in Table 2.
- Example 14 In the case of Example 1, except that the amount of the flame retardant D-1 used was 2.0 parts by weight and the amount of the flame retardant D-2 used was 1.0 parts by weight, compared to the case of Example 1. The experiment was carried out in exactly the same way. The results are shown in Table 3.
- Example 16 The experiment was performed in exactly the same manner as in Example 1, except that the amount of flame retardant D-1 used was 1.0 part by weight compared to Example 1. The results are shown in Table 3.
- the molded product obtained from the urethane resin composition according to the present invention has a small calorific value when combusted, it can exhibit excellent flame retardancy.
- the molded body is preferably used for a material used for at least one of a building, an automobile, a railway vehicle, a ship, an airplane, and the like.
- the molded product of the urethane resin composition according to the present invention is excellent in flame retardancy, it is suitable for structural materials such as buildings, wall materials, floor materials, ceiling materials, heat insulating materials, seat materials such as vehicles, bed materials, etc.
- the urethane resin composition of the invention can be widely applied.
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Abstract
Le problème de l'invention réside dans une composition de résine d'uréthane présentant une ininflammabilité exceptionnelle. La solution selon l'invention porte sur une composition de résine d'uréthane contenant une résine d'uréthane contenant un composé polyisocyanate et un composé polyol, un retardateur de flamme et un catalyseur de trimérisation destiné à favoriser une réaction de trimérisation des groupes isocyanate contenus dans le composé polyisocyanate, la composition de résine d'uréthane étant caractérisée en ce que le retardateur de flamme contient du phosphore rouge et un retardateur de flamme contenant du phosphate, le phosphore rouge se situant dans la plage de 3,0 à 20 parties en poids et le retardateur de flamme contenant du phosphate se situant dans la plage de 1,0 à 18 parties en poids par 100 parties en poids de résine d'uréthane.
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Cited By (4)
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JP2015193839A (ja) * | 2014-03-27 | 2015-11-05 | 積水化学工業株式会社 | 難燃性ウレタン樹脂組成物 |
WO2016017797A1 (fr) * | 2014-08-01 | 2016-02-04 | 積水化学工業株式会社 | Composition de résine polyuréthane ignifuge |
EP3357947A4 (fr) * | 2015-09-30 | 2019-04-17 | Sekisui Chemical Co., Ltd. | Mousse de polyuréthane rigide ignifugeante |
US10676559B2 (en) | 2013-01-20 | 2020-06-09 | Sekisui Chemical Co., Ltd. | Flame-retardant urethane resin composition |
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- 2014-07-11 JP JP2014542631A patent/JP6378088B2/ja active Active
- 2014-07-11 WO PCT/JP2014/003705 patent/WO2015004928A1/fr active Application Filing
- 2014-07-11 TW TW103123945A patent/TW201510071A/zh unknown
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US10676559B2 (en) | 2013-01-20 | 2020-06-09 | Sekisui Chemical Co., Ltd. | Flame-retardant urethane resin composition |
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WO2016017797A1 (fr) * | 2014-08-01 | 2016-02-04 | 積水化学工業株式会社 | Composition de résine polyuréthane ignifuge |
EP3357947A4 (fr) * | 2015-09-30 | 2019-04-17 | Sekisui Chemical Co., Ltd. | Mousse de polyuréthane rigide ignifugeante |
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JPWO2015004928A1 (ja) | 2017-03-02 |
JP6378088B2 (ja) | 2018-08-22 |
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