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
  • C08G18/18—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
  • C08G18/08—Processes
  • C08G18/16—Catalysts
  • C08G18/22—Catalysts containing metal compounds
  • C08G18/24—Catalysts containing metal compounds of tin
  • C08G18/242—Catalysts containing metal compounds of tin organometallic compounds containing tin-carbon bonds
• • 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
• • 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
  • C08G2101/00—Manufacture of cellular products
• • 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 same.
• 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 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 catalyst composition for producing polyurethane foam comprising a tin compound (A) represented by the following chemical formula (1) and a tin compound (B) represented by the following chemical formula (2):
• R 1 , R 2 , and R 3 are each a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms and may be the same or different from each other.
• R 4 and R 6 are each a substituted or unsubstituted hydrocarbon group having 1 to 20 carbon atoms, or a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms and may be the same or different from each other.
• R 5 is a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms, or a halogen.
• R 7 , R 8 and R 9 are each a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, and may be the same or different.
• the tin compound (A) represented by the chemical formula (1) is at least one of acetylacetone-tin neodecanoate, ethyl acetoacetate-tin neodecanoate, 3,5-heptanedione-tin neodecanoate, 3-chloroacetylacetone-tin neodecanoate, dipivaloylmethane-tin neodecanoate, 1,3-diphenyl-1,3-propanedione-tin n
• the catalyst composition of the present invention has a practical curing speed.
• polyurethane foam produced using the catalyst composition of the present invention has excellent breathability and therefore satisfies the breathability requirements.
• the catalyst composition of the present invention achieves the above-mentioned excellent effects 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, a catalyst composition for producing polyurethane foam is provided which is highly safe, has a practical curing speed, and produces polyurethane foam that satisfies the breathability requirements.
• the catalyst composition of the present invention contains a tin compound (A) and a tin compound (B).
• the catalyst composition of the present invention preferably does not contain tin 2-ethylhexanoate, but may contain it.
• the content of tin 2-ethylhexanoate is, for example, 0 to 10 mass%, preferably 0 to 5 mass%, and more preferably 0 to 1 mass%.
• the content of tin compound (A) in the catalyst composition of the present invention is preferably 0.1 to 200 mass% relative to tin compound (B), more preferably 0.5 to 100 mass%, even more preferably 1 to 50 mass%, and even more preferably 5 to 30 mass%.
• the content of tin compound (A) relative to tin compound (B) is specifically, for example, 0.1, 0.5, 1, 2, 3, 4, 5, 10, 15, 20, 25, 30, 40, 50, 100, or 200 mass%, and may be in a range between any two of the numerical values exemplified here.
• the amount of the catalyst composition of the present invention used is not particularly limited, but is preferably in the range of 0.01 to 1 part by mass, and 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.
• the catalyst composition of the present invention may further contain an additional catalyst, if necessary.
• additional catalyst include other resinification catalysts, foaming catalysts, organometallic catalysts, carboxylate metal salt catalysts, and quaternary ammonium salt catalysts.
• additional catalyst include other resinification catalysts, foaming catalysts, organometallic catalysts, carboxylate metal salt catalysts, and quaternary ammonium salt catalysts.
• other resinification catalysts include 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)-piperaz
• 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.
• Tin compound (A) The tin compound (A) used in the present invention is represented by the chemical formula (1).
• R 1 , R 2 and R 3 are each a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms and may be the same or different from each other.
• R 4 and R 6 are each a substituted or unsubstituted hydrocarbon group having 1 to 20 carbon atoms or a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms and may be the same or different from each other.
• R 5 is a hydrogen atom, a hydrocarbon group having 1 to 10 carbon atoms or a halogen.
• examples of the alkyl group having 1 to 10 carbon atoms represented by R 1 , R 2 , and R 3 include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, 3-methylbutyl, pentyl, hexyl, heptyl, octyl, ethylhexyl, nonyl, and decyl.
• examples of the substituted or unsubstituted hydrocarbon group having 1 to 20 carbon atoms represented by R 4 and R 6 include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, ethylhexyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, icosyl, phenyl, etc.
• These alkyl groups may be substituted with an alkoxy group, a hydroxyl group, a halogen, a phenyl group, etc.
• substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentoxy, hexanoxy, heptanoxy, octanoxy, ethylhexanoxy, nonanoxy, decanoxy, undecanoxy, dodecanoxy, tridecanoxy, tetradecanoxy, pentadecanoxy, hexadecanoxy, heptadecoxy, octadecoxy, and nonadecanoxy.
• These alkoxy groups may be substituted with alkoxy groups, hydroxyl groups, halogens, phenyl groups, and the like.
• examples of the hydrocarbon group having 1 to 10 carbon atoms represented by R 5 include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, ethylhexyl, nonyl, decyl, and phenyl.
• halogen include fluoride, chloro, bromo, and iodine.
• tin compound (A) examples include acetylacetone-tin neodecanoate, ethyl acetoacetate-tin neodecanoate, 3,5-heptanedione-tin neodecanoate, 3-chloroacetylacetone-tin neodecanoate, dipivaloylmethane-tin neodecanoate, 1,3-diphenyl-1,3-propanedione-tin neodecanoate, 1-phenyl-1,3-butanedione-tin neodecanoate, bis(acetylacetone)tin, bis(ethyl acetoacetate)tin, bis(3,5-heptanedione)tin, bis(3-chloroacetylacetone)tin, bis(dipivaloylmethane)tin, bis(1,3-diphenyl-1,3
• Tin compound (B) The tin compound (B) used in the present invention is represented by the chemical formula (2).
• R 7 , R 8 and R 9 are each a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, and may be the same or different.
• examples of the alkyl group having 1 to 10 carbon atoms represented by R 7 , R 8 , and R 9 include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, 3-methylbutyl, pentyl, hexyl, heptyl, octyl, ethylhexyl, nonyl, decyl, etc.
• Specific examples of the number of carbon atoms are 1, 2, 3, 4, 5, 6, 7, 8, 9, and 10, and may be within a range between any two of the numerical values exemplified here.
• tin compounds (B) include tin diacetate, tin dipivalate, tin bis(2-ethylbutyrate), tin bis(2-ethylhexanoate), tin bis(n-octylate), tin bis(neononanoate), tin bis(isononanoate), and tin bis(neodecanoate), with tin bis(2-ethylhexanoate), tin bis(isononanoate), and tin bis(neodecanoate) being preferred.
• These tin compounds may be used alone or in combination of two or more.
• the catalyst composition of the present invention may be prepared by producing the tin compound (A) and the tin compound (B) separately and then mixing them, or the tin compound (A) and the tin compound (B) may be produced simultaneously.
• the tin compounds (A) and (B) can be produced by known methods. For example, they can be produced by heating various carboxylic acids and/or ⁇ -diketone compounds with stannous chloride in a solvent in the presence of an alkali compound at a temperature of about 30 to 70° C. Commercially available products can also be used, such as 2-ethylhexanoic acid, isononanoic acid, neodecanoic acid PG, and Versatic 10.
• polyurethane Foam 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 the catalyst composition.
• the active hydrogen-containing organic compound is an organic compound 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 the active hydrogen-containing organic compound include an organic compound having two or more of the above-mentioned functional groups in the molecule.
• the active hydrogen-containing organic compound includes a polyol (a compound having two or more hydroxyl groups at the molecular end).
• the active hydrogen-containing organic compound may include only a polyol, or may include both a polyol and an active hydrogen-containing organic compound other than a polyol (or a polyamine, etc.).
• the polyol is not particularly limited as long as it is generally used in the production of a urethane composition, and examples thereof include polyether polyol, polyester polyol, polymer polyol, 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.
• polyhydric alcohols examples include oil-modified polyester polyols obtained by blending higher fatty acids such as coconut oil fatty acid, linseed oil fatty acid, soybean oil fatty acid, cottonseed oil fatty acid, tung oil fatty acid, and castor oil fatty acid in the acid component.
• lactone polymers include those obtained by ring-opening polymerization of ⁇ -caprolactam, ⁇ -methyl- ⁇ -caprolactam, ⁇ -methyl- ⁇ -caprolactam, etc.
• 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.
• Flame-retardant polyols include, for example, phosphorus-containing polyols obtained by adding alkylene oxide to phosphoric acid compounds, polyols obtained by ring-opening polymerization of epichlorohydrin or trichlorobutylene oxide, polyether polyols, polyester polyols, and halogen-containing polyols in which the hydrogen atoms of acrylic polyols are partially or completely replaced with fluorine atoms, etc.
• Polyamines include, for example, aliphatic polyamines and aromatic polyamines.
• Aliphatic polyamines include ethylenediamine and polyether polyamines
• aromatic polyamines include 3,3'-dichloro-4,4'-diaminodiphenylmethane, DETDA, 2,4-diamino-3,5-diethyltoluene, 2,6-diamino-3,5-diethyltoluene, and mixtures thereof, such as Albemarle's Ethacure 100 (2,4-isomer/2,6-isomer mass ratio of approximately 80/20), Albemarle's Ethacure 420 (4,4'-methylenebis(N-sec-butylaniline)), and 4,4'-methylenebis(2-ethyl-6-methylaniline).
• active hydrogen-containing organic compounds can be used alone or in combination of two or more.
• the active hydrogen-containing organic compound contains both a polyol and a polyamine. In this case, the workability, curability, and mechanical properties of the composition are particularly good.
• Polyisocyanates are compounds having two or more isocyanate groups in the molecule. There are no particular limitations on the polyisocyanate as long as it is a commonly used compound. Examples of the polyisocyanate include alkylene diisocyanates such as trimethylene diisocyanate, trimethylhexamethylene diisocyanate, tetramethylene diisocyanate, and hexamethylene diisocyanate; cycloalkylene diisocyanates such as bis(isocyanatemethyl)cyclohexane, cyclopentane diisocyanate, cyclohexane diisocyanate, and isophorone diisocyanate; aromatic diisocyanates such as tolylene diisocyanate, phenylene diisocyanate, diphenylmethane diisocyanate, and diphenyl ether diisocyanate; aromatic aliphatic diisocyanates such as xylylene diisocyanate and di
• isocyanate tetraisocyanates such as diphenyldimethylmethane tetraisocyanate, polymerized polyisocyanates such as tolylene diisocyanate dimer and trimer, and terminal isocyanate-containing compounds obtained by reacting an excess amount of these polyisocyanates with a low-molecular-weight active hydrogen-containing organic compound such as ethylene glycol, propylene glycol, diethylene glycol, trimethylolpropane, hydrogenated bisphenol A, hexanetriol, glycerin, pentaerythritol, castor oil, triethanolamine, etc.
• a low-molecular-weight active hydrogen-containing organic compound such as ethylene glycol, propylene glycol, diethylene glycol, trimethylolpropane, hydrogenated bisphenol A, hexanetriol, glycerin, pentaerythritol, castor oil, triethanolamine, etc.
• the content of the polyisocyanate of the present invention is preferably 1 to 100 parts by mass, more preferably 5 to 70 parts by mass, more preferably 20 to 60 parts by mass, and even more preferably 30 to 50 parts by mass, relative to 100 parts by mass of the active hydrogen-containing organic compound.
• Specific examples of this content are 1, 5, 10, 15, 20, 30, 40, 50, 60, 70, 80, 90, and 100 parts by mass, and may be within a range between any two of the numerical values exemplified here.
• a blowing agent a surfactant, a flame retardant, a crosslinking agent, etc.
• a colorant an antioxidant, other conventionally known additives, etc. can also be used.
• water As the blowing agent, water, alternative fluorocarbons, and hydrocarbons such as dichloromethane or pentane can be used alone or in combination. Water is particularly preferred as the blowing agent.
• carbon dioxide gas is generated during the reaction of polyol with polyisocyanate, and the foaming is caused by the carbon dioxide gas.
• the amount of water used as the blowing agent is preferably 1.0 to 5.0 parts by mass, more preferably 2.0 to 4.0 parts by mass, per 100 parts by mass of polyol.
• the foam stabilizer may be any foam stabilizer that is commonly used as a polyurethane foam raw material, such as silicone compounds and nonionic surfactants.
• the amount of foam stabilizer is preferably 0.1 to 4.0 parts by mass, more preferably 0.2 to 2.0 parts by mass, and even more preferably 0.3 to 1.0 parts by mass, per 100 parts by mass of polyol.
• the polyurethane foam of the present invention can be manufactured, for example, by mixing and stirring the above-mentioned materials using a mixer or a dedicated polyurethane foaming machine, and then injecting the mixture into a container or mold and foaming it.
• ⁇ Production Example 1 (Acetylacetone-Tin Neodecanoate ⁇ A1>)> 1.0 g of tin(II) ethoxide, 0.48 g of acetylacetone, 0.82 g of neodecanoic acid, and 2 mL of ethanol were weighed into a 10 ml eggplant-shaped flask equipped with a nitrogen inlet tube, and stirred with a magnetic stirrer until dissolved. The solvent was removed by vacuum concentration, yielding 1.86 g of acetylacetone-tin neodecanoate ⁇ A1> as a yellow liquid. 119 Sn NMR analysis of this compound confirmed a new peak (-0.558 ppm) for acetylacetone-tin neodecanoate.
• ⁇ Production Example 2 (3,5-heptanedione-tin neodecanoate ⁇ A2>)> 1.0 g of tin(II) ethoxide, 0.61 g of 3,5-heptanedione, 0.82 g of neodecanoic acid, and 2 mL of ethanol were weighed into a 10 ml eggplant-shaped flask equipped with a nitrogen inlet tube, and stirred with a magnetic stirrer until dissolved. The solvent was removed by vacuum concentration, yielding 2.00 g of yellow liquid 3,5-heptanedione-tin neodecanoate ⁇ A2>. 119 Sn NMR analysis of this compound confirmed a new peak (-0.558 ppm) for 3,5-heptanedione-tin neodecanoate.
• ⁇ Production Example 4 (Dipivaloylmethane-Tin Neodecanoate ⁇ A4>)> 1.0 g of tin(II) ethoxide, 0.88 g of dipivaloylmethane, 0.82 g of neodecanoic acid, and 2 mL of ethanol were weighed into a 10 ml eggplant-shaped flask equipped with a nitrogen inlet tube, and stirred with a magnetic stirrer until dissolved. The solvent was removed by vacuum concentration, yielding 2.27 g of a yellow liquid dipivaloylmethane-tin neodecanoate ⁇ A4>. 119 Sn NMR analysis of this compound confirmed a new peak (-0.558 ppm) for dipivaloylmethane-tin neodecanoate.
• Tin di-n-octanoate ⁇ B1> 1.0 g of tin(II) ethoxide, 1.38 g of n-octanoic acid, and 2 mL of ethanol were weighed into a 10 mL eggplant-shaped flask equipped with a nitrogen inlet tube, and stirred with a magnetic stirrer until dissolved. The solvent was removed by vacuum concentration, yielding 1.94 g of a pale yellow solid, tin di-n-octanoate ⁇ B1>.
• Tin di-n-nonanoate ⁇ B2> 1.0 g of tin(II) ethoxide, 1.52 g of n-nonanoic acid, and 2 mL of ethanol were weighed into a 10 mL eggplant-shaped flask equipped with a nitrogen inlet tube, and stirred with a magnetic stirrer until dissolved. The solvent was removed by vacuum concentration, yielding 2.07 g of a pale yellow solid, tin di-n-nonanoate ⁇ B2>.
• Tin bis(isononanoate) ⁇ B3> 1.0 g of tin(II) ethoxide, 1.52 g of isononanoic acid, and 2 mL of ethanol were weighed into a 10 mL eggplant-shaped flask equipped with a nitrogen inlet tube, and stirred with a magnetic stirrer until dissolved. The solvent was removed by vacuum concentration to obtain 2.07 g of tin bis(isononanoate) ⁇ B3> as a pale yellow solid.
• Tin bis(neodecanoate) Neostan U-50 (manufactured by Nitto Chemical Industry Co., Ltd.)
• Isocyanate Toluene diisocyanate (TDI), manufactured by Tokyo Chemical Industry Co., Ltd.
• the catalysts of Examples 1 to 8 and 17 all had a content of tin compound (A) of more than 50% by mass relative to the tin compound (B), while the catalysts of Examples 9 to 16 and 18 to 30 all had a content of tin compound (A) of 5 to 30% by mass relative to the tin compound (B), and therefore the difference in curability is considered to be due to the difference in the content of tin compound (A) relative to the tin compound (B).

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• 2024
  • 2024-05-24 EP EP24815413.0A patent/EP4722268A1/en active Pending
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  • 2024-05-24 CN CN202480028012.7A patent/CN121219338A/zh active Pending
  • 2024-05-24 JP JP2025524070A patent/JPWO2024247930A1/ja active Pending
  • 2024-05-24 WO PCT/JP2024/019254 patent/WO2024247930A1/ja not_active Ceased

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