Classifications

• • 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
  • C08G18/24—Catalysts containing metal compounds of tin
  • C08G18/244—Catalysts containing metal compounds of tin tin salts of carboxylic acids
• • 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
  • C08G18/165—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 covered by C08G18/18 and C08G18/24
• • 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
  • C08G18/20—Heterocyclic amines; Salts thereof
  • C08G18/2045—Heterocyclic amines; Salts thereof containing condensed heterocyclic rings
  • C08G18/2063—Heterocyclic amines; Salts thereof containing condensed heterocyclic rings having two nitrogen atoms in the condensed ring system
• • 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
  • C08G18/4825—Polyethers containing two hydroxy groups
• • 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
  • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
  • C08G18/72—Polyisocyanates or polyisothiocyanates
  • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
  • C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
  • C08G18/7614—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring
  • C08G18/7621—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring being toluene diisocyanate including isomer mixtures
• • 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
  • C08G2110/0008—Foam properties flexible
• • 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

Definitions

• the present invention relates to a catalyst composition for producing polyurethane foam, and a method for producing polyurethane foam using the catalyst composition obtained by this production method.
• Polyurethane foam is manufactured using polyol and polyisocyanate as the main raw materials, with the addition of catalysts, blowing agents, surfactants, etc., and is used in various types of foam. For example, it is widely used after being processed into soft foams for cushions, mattresses, etc., and hard foams for building materials, home appliances, etc.
• Amine compounds and other resinification catalysts as well as metal compounds and amine compounds and other foaming catalysts, are used as catalysts for forming polyurethane foam.
• the metal compounds used include tin, lead, bismuth, and zirconium, and among these, tin octoate (tin 2-ethylhexanoate) has been widely used (Patent Documents 1 and 2).
• the present invention was made in consideration of these circumstances, and aims to provide a method for producing a catalyst composition for producing polyurethane foam that is highly safe, has a practical curing speed, and produces polyurethane foam that meets the breathability requirements.
• a method for producing a catalyst composition for producing polyurethane foam comprising a step of mixing 2.10 to 4.00 moles of at least one carboxylic acid selected from neodecanoic acid, neononanoic acid, and isononanoic acid with 1 mole of stannous chloride.
• a method for producing a polyurethane foam comprising reacting an active hydrogen-containing organic compound containing a polyol with a polyisocyanate in the presence of the catalyst composition produced by the method according to [1] or [2].
• the catalyst composition produced by the method of the present invention has a practical curing speed.
• polyurethane foam produced using the catalyst composition produced by the method of the present invention has excellent breathability and therefore satisfies the breathability requirements.
• the catalyst composition produced by the method of the present invention has the above-mentioned excellent effects even without containing tin 2-ethylhexanoate, so there is no need to contain tin 2-ethylhexanoate and it is highly safe. Therefore, according to the present invention, there is provided a method for producing a catalyst composition for producing polyurethane foam that is highly safe, has a practical curing speed, and produces polyurethane foam that satisfies the breathability requirements.
• the method for producing a catalyst composition for producing polyurethane foam of the present invention comprises a step of mixing 2.10 to 4.00 moles of at least one carboxylic acid selected from neodecanoic acid, neononanoic acid, and isononanoic acid with 1 mole of stannous chloride. This mixing step causes 1 mole of stannous chloride to react with the carboxylic acid to obtain a catalyst composition suitable for producing polyurethane foam (the catalyst composition obtained in this step is referred to as "catalyst composition A").
• Stannous chloride is a divalent tin compound represented by SnCl2 , and may be an anhydride or a hydrate (e.g., dihydrate). From the viewpoints of catalytic activity and gas permeability, neodecanoic acid is particularly preferred as the carboxylic acid.
• a catalyst composition in which the coordination number of carboxylate ions ( RCOO- ) and carboxylic acids (RCOOH) to the tin atom exceeds 2 is obtained.
• the ratio of carboxylic acid to 1 mole of stannous chloride is preferably 2.10 to 3.00 moles, more preferably 2.10 to 2.50 moles, and even more preferably 2.10 to 2.30. From the viewpoint of breathability, this ratio is preferably 2.20 to 4.00 moles, and even more preferably 2.50 to 3.00 moles. From the viewpoint of the balance between curability and breathability, this ratio is preferably 2.20 to 2.50 moles.
• this ratio is, for example, 2.10, 2.15, 2.20, 2.25, 2.30, 2.40, 2.50, 2.60, 2.70, 2.80, 2.90, 3.00, 3.10, 3.20, 3.30, 3.40, 3.50, 3.60, 3.70, 3.80, 3.90, or 4.00 moles, or may be in a range between any two of the values exemplified here.
• stannous chloride and carboxylic acid in the presence of an alkaline compound.
• An example of an alkaline compound is sodium hydroxide.
• carboxylic acid Before mixing stannous chloride and carboxylic acid, it is preferable to mix the carboxylic acid with an aqueous solution of an alkaline compound and mix the resulting aqueous solution with stannous chloride. It is preferable to mix stannous chloride with carboxylic acid in the form of an aqueous solution of stannous chloride hydrate.
• the temperature of the aqueous solution obtained by mixing is preferably 30 to 70°C. This is because the reaction tends to proceed quickly in this case.
• the method for producing a polyurethane foam of the present invention is characterized by reacting and foaming an active hydrogen-containing organic compound including a polyol with a polyisocyanate in the presence of a catalyst composition.
• Catalyst composition As the catalyst composition used in the production of polyurethane foam, only the above-mentioned catalyst composition A may be used, or an additional catalyst may be used as necessary.
• the amount of catalyst composition A used is not particularly limited, but is preferably in the range of 0.01 to 1 part by mass, more preferably in the range of 0.05 to 0.5 parts by mass, per 100 parts by mass of the active hydrogen-containing organic compound including polyol.
• Additional catalysts include other resinification catalysts, foaming catalysts, organometallic catalysts, carboxylate metal salt catalysts, or quaternary ammonium salt catalysts.
• Other resinification catalysts include, for example, 1,4-diazabicyclo[2.2.2]octane (DACBO), triethylenediamine, N,N-dicyclohexylmethylamine, N,N-dimethylcyclohexylamine, N,N-dimethylaminohexanol, 1,2-dimethylimidazole, N.(N',N'-dimethylaminoethyl)-morpholine, tetramethylguanidine, dimethylaminoethanol, N-methyl-N'-(2hydroxyethyl)-piperazine.
• DACBO 1,4-diazabicyclo[2.2.2]octane
• foaming catalyst examples include amine catalysts such as bis(2-dimethylaminoethyl)ether, triethylamine, dimethylaminoethoxyethanol, N,N,N'-trimethylaminoethylethanolamine, and N,N,N',N",N"-pentamethyldiethylenetriamine.
• the amount of the additional catalyst is preferably 0.01 to 1.0 parts by mass, more preferably 0.02 to 0.5 parts by mass, and even more preferably 0.05 to 0.2 parts by mass, per 100 parts by mass of polyol.
• the additional catalyst may contain tin 2-ethylhexanoate, but preferably does not contain tin 2-ethylhexanoate. If catalyst composition A is 100% by mass, the content of tin 2-ethylhexanoate is, for example, 0 to 10% by mass, preferably 0 to 5% by mass, and more preferably 0 to 1% by mass.
• Active hydrogen-containing organic compounds including polyols
• Active hydrogen-containing organic compounds are organic compounds having active hydrogen.
• the active hydrogen is a hydrogen of a functional group capable of forming a urethane bond or a urea bond by reacting with an isocyanate. Examples of such functional groups include a hydroxyl group and an amino group.
• Examples of active hydrogen-containing organic compounds include organic compounds having two or more of the above-mentioned functional groups in the molecule.
• active hydrogen-containing organic compounds include polyols (compounds having two or more hydroxyl groups at the molecular end).
• Examples of active hydrogen-containing organic compounds include only polyols, and may include both polyols and active hydrogen-containing organic compounds other than polyols (or polyamines, etc.).
• the polyols are not particularly limited as long as they are generally used in the production of urethane compositions, and examples of such polyols include polyether polyols, polyester polyols, polymer polyols, and flame-retardant polyols such as phosphorus-containing polyols and halogen-containing polyols. These polyols can be used alone or in appropriate mixtures.
• polyether polyols examples include those obtained by ring-opening addition polymerization of, for example, ethylene oxide, propylene oxide, or mixtures of these using ethylene glycol, propylene glycol, glycerin, pentaerythritol, ethylenediamine, ethanolamine, diethanolamine, or the like as an initiator, or polytetramethylene ether glycol obtained by ring-opening polymerization of tetrahydrofuran.
• polyester polyols include those obtained by the condensation reaction of polybasic carboxylic acids such as maleic acid, fumaric acid, succinic acid, adipic acid, sebacic acid, azelaic acid, phthalic acid, isophthalic acid, terephthalic acid, and trimellitic acid with polyhydric alcohols, and lactone polymers.
• polybasic carboxylic acids such as maleic acid, fumaric acid, succinic acid, adipic acid, sebacic acid, azelaic acid, phthalic acid, isophthalic acid, terephthalic acid, and trimellitic acid with polyhydric alcohols, and lactone polymers.
• polyhydric alcohols include ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, 1,3-butylene glycol, 1,4-butylene glycol, 1,5-pentanediol, 1,6-hexanediol, neopentyl glycol, decamethylene glycol, 2,4,4-trimethyl-1,3-pentanediol, cyclohexanediol, cyclohexanedimethanol, xylylene glycol, hydroquinone bis(hydroxyethyl ether), hydrogenated bisphenol A, trimethylolpropane, glycerin, 1,2,6-hexanetriol, pentaerythritol, castor oil, and the like.
• polymer polyols examples include compounds obtained by polymerizing or copolymerizing polymerizable monomers containing hydroxyl groups, such as hydroxyethyl acrylate, hydroxybutyl acrylate, and trimethylolpropane acrylate monoester, either alone or with monomers copolymerizable therewith, such as acrylic acid, methacrylic acid, styrene, acrylonitrile, and ⁇ -methylstyrene.
• hydroxyl groups such as hydroxyethyl acrylate, hydroxybutyl acrylate, and trimethylolpropane acrylate monoester, either alone or with monomers copolymerizable therewith, such as acrylic acid, methacrylic acid, styrene, acrylonitrile, and ⁇ -methylstyrene.

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• Chemical & Material Sciences (AREA)
• Health & Medical Sciences (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Medicinal Chemistry (AREA)
• Polymers & Plastics (AREA)
• Organic Chemistry (AREA)
• Polyurethanes Or Polyureas (AREA)
• Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)

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Citations (9)

• 2024
  • 2024-06-17 JP JP2025528047A patent/JPWO2024262458A1/ja active Pending
  • 2024-06-17 WO PCT/JP2024/021880 patent/WO2024262458A1/ja not_active Ceased
  • 2024-06-17 EP EP24825859.2A patent/EP4733342A1/en active Pending
  • 2024-06-17 TW TW113122267A patent/TW202508704A/zh unknown
  • 2024-06-17 CN CN202480029631.8A patent/CN121039188A/zh active Pending

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