WO2021210534A1 - ウレタン化合物 - Google Patents

ウレタン化合物 Download PDF

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Publication number
WO2021210534A1
WO2021210534A1 PCT/JP2021/015176 JP2021015176W WO2021210534A1 WO 2021210534 A1 WO2021210534 A1 WO 2021210534A1 JP 2021015176 W JP2021015176 W JP 2021015176W WO 2021210534 A1 WO2021210534 A1 WO 2021210534A1
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WO
WIPO (PCT)
Prior art keywords
urethane
compound
diisocyanate
urethane compound
water
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2021/015176
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English (en)
French (fr)
Japanese (ja)
Inventor
育男 山本
晋一 南
斌 周
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Daikin Industries Ltd
Original Assignee
Daikin Industries Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Daikin Industries Ltd filed Critical Daikin Industries Ltd
Priority to KR1020227028927A priority Critical patent/KR102822550B1/ko
Priority to EP21789359.3A priority patent/EP4137479A4/en
Priority to CN202180016271.4A priority patent/CN115135637B/zh
Priority to JP2022515372A priority patent/JP7469695B2/ja
Publication of WO2021210534A1 publication Critical patent/WO2021210534A1/ja
Priority to US17/964,526 priority patent/US12473394B2/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • 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
    • C08G18/80—Masked polyisocyanates
    • C08G18/8061—Masked polyisocyanates masked with compounds having only one group containing active hydrogen
    • C08G18/8064—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with monohydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C265/00—Derivatives of isocyanic acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C07D251/30—Only oxygen atoms
    • C07D251/34—Cyanuric or isocyanuric esters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1818—C13or longer chain (meth)acrylate, e.g. stearyl (meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/22—Esters containing halogen
    • C08F220/24—Esters containing halogen containing perhaloalkyl radicals
    • 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
    • C08G18/246—Catalysts containing metal compounds of tin tin salts of carboxylic acids containing also 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
    • C08G18/2805—Compounds having only one group containing active hydrogen
    • C08G18/2815—Monohydroxy compounds
    • C08G18/283—Compounds containing ether groups, e.g. oxyalkylated monohydroxy compounds
    • 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
    • C08G18/2805—Compounds having only one group containing active hydrogen
    • C08G18/285—Nitrogen containing compounds
    • 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
    • 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
    • C08G18/703—Isocyanates or isothiocyanates transformed in a latent form by physical means
    • C08G18/705—Dispersions of isocyanates or isothiocyanates in a liquid medium
    • C08G18/706—Dispersions of isocyanates or isothiocyanates in a liquid medium the liquid medium being water
    • 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
    • C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
    • C08G18/78—Nitrogen
    • C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
    • C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
    • C08G18/792—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/80—Masked polyisocyanates
    • 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
    • C08G18/80—Masked polyisocyanates
    • C08G18/8003—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen
    • C08G18/8054—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/38
    • C08G18/8058—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/38 with compounds of C08G18/3819
    • 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
    • C08G18/80—Masked polyisocyanates
    • C08G18/8061—Masked polyisocyanates masked with compounds having only one group containing active hydrogen
    • C08G18/807—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with nitrogen containing compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes
    • C09D175/08—Polyurethanes from polyethers
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/263—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof
    • D06M15/277—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof containing fluorine
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/564—Polyureas, polyurethanes or other polymers having ureide or urethane links; Precondensation products forming them
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/564—Polyureas, polyurethanes or other polymers having ureide or urethane links; Precondensation products forming them
    • D06M15/568—Reaction products of isocyanates with polyethers
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2101/00—Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
    • D06M2101/02—Natural fibres, other than mineral fibres
    • D06M2101/04—Vegetal fibres
    • D06M2101/06—Vegetal fibres cellulosic
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
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    • D06M2101/00—Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
    • D06M2101/16—Synthetic fibres, other than mineral fibres
    • D06M2101/30—Synthetic polymers consisting of macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M2101/34—Polyamides
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
    • D06M2200/10—Repellency against liquids
    • D06M2200/11—Oleophobic properties
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
    • D06M2200/10—Repellency against liquids
    • D06M2200/12—Hydrophobic properties

Definitions

  • the present disclosure relates to a urethane compound and an aqueous urethane composition containing a urethane compound.
  • Patent Document 1 International Publication No. 2006/038466 discloses an aqueous dispersion type polyurethane composition containing a polyisocyanate represented by a specific chemical formula as an essential component.
  • Patent Document 2 Japanese Patent Publication No.
  • 2014-210882 comprises a polyisocyanate unit, a polyethylene oxide unit which is a single-terminal hydroxyl group, and a blocking agent unit, and the number ratio of allophanate group / isocyanurate group is 30/100.
  • a blocked polyisocyanate composition of ⁇ 200/100 is disclosed.
  • cross-linking agents cannot always assist in sufficient water and oil repellency, and there has been a demand for higher performance cross-linking agents that assist in washing durability.
  • the present disclosure provides a urethane compound formed from a long-chain alcohol having a hydrocarbon group having 7 to 40 carbon atoms.
  • Aspect 2 Moreover, (A3) blocking agent, and (A4) alcohol compound, The urethane compound according to embodiment 1, which comprises a unit formed from at least one selected from.
  • Aspect 3 The isocyanate (A1) is tolylene diisocyanate (TDI), diphenylmethane diisocyanate (MDI), MDI oligomer, naphthalene-1,5-diisocyanate, xylylene diisocyanate, hexamethylene diisocyanate (HDI), 4,4-dicyclohexylmethane diisocyanate, norbornan. 10.
  • the aspect 1 or 2 wherein the diisocyanate, isophorone diisocyanate (IPDI), diisocyanate adduct, allophanate-modified product, biuret-modified product, isocyanurate-modified product or carbodiimide-modified product, and at least one selected from urethane prepolymers.
  • IPDI isophorone diisocyanate
  • Urethane compound Urethane compound.
  • Aspect 5 2. Urethane compound.
  • Aspect 6 The alcohol compound (A4) is a monool or polyol, Monool is a compound in which a C 2 or C 3 alkylene oxide is added to a starting monoalcohol having 1 to 10 carbon atoms.
  • Aspect in which the polyol is a polyol having three or more diols and hydroxyl groups, and is at least one selected from low molecular weight polyols, polyether polyols, polyester polyols, polyester polycarbonate polyols, and crystalline or non-crystalline polycarbonate polyols.
  • the urethane compound according to any one of 2 to 5.
  • Aspect 7 The urethane compound according to any one of aspects 1 to 6 and at least one selected from the group consisting of polyisocyanate (A1), long-chain alcohol (A2), blocking agent (A3) and alcohol compound (A4) are included. Urethane mixture.
  • Aspect 8 An aqueous urethane composition comprising (A) the urethane compound according to any one of aspects 1 to 6 and (B) water.
  • Aspect 9 The aqueous urethane composition according to aspect 8, wherein the aqueous urethane composition is an aqueous dispersion.
  • Aspect 10 The water-based urethane composition according to aspect 8 or 9, wherein the water-based urethane composition is a cross-linking agent or an auxiliary agent.
  • Aspect 11 The production of the aqueous urethane composition according to any one of aspects 8 to 10, wherein the isocyanate (A1) and the long-chain alcohol (A2) are mixed and reacted in an organic solvent, and then mixed with water.
  • Aspect 12 A method for treating a base material, which comprises treating the base material with a surface treatment composition containing the urethane compound according to any one of aspects 1 to 6.
  • Aspect 13 A treated textile product in which the urethane compound according to any one of aspects 1 to 6 is attached to an object to be treated as a crosslinked product.
  • a urethane compound that functions as an auxiliary agent for improving the performance of a surface treatment agent such as a water-repellent oil-repellent agent can be obtained.
  • Urethane compounds help the surface treatment agent to provide high water and oil repellency.
  • high washing durability can be obtained, and in particular, high washing durability can be obtained with respect to water repellency.
  • the present invention relates to an aqueous urethane composition containing (A) a urethane compound and (B) water.
  • Z is a directly bonded or divalent or trivalent hydrocarbon group having 1 to 5 carbon atoms. n is 1 or 2. ] It is formed from the long-chain alcohol indicated by. That is, the urethane compound (A) has a unit formed from the polyisocyanate (A1) and a unit formed from the long-chain alcohol (A2).
  • the urethane compound (A) is (A3) blocking agent, and (A4) alcohol compound, It may have a unit formed from at least one selected from.
  • the urethane compound (A) preferably has both a unit formed from the blocking agent (A3) and a unit formed from the alcohol compound (A4).
  • the urethane compound (A) may be formed from the following components.
  • Ingredient (A1) + Ingredient (A2) Ingredient (A1) + Ingredient (A2) + Ingredient (A3) Ingredient (A1) + Ingredient (A2) + Ingredient (A4)
  • any one of the polyisocyanate (A1), the long chain alcohol (A2), the blocking agent (A3) and the alcohol compound (A4) may be at least partially unreacted. Therefore, the present disclosure comprises at least one selected from the group consisting of polyisocyanate (A1), long chain alcohol (A2), blocking agent (A3) and alcohol compound (A4), and urethane containing urethane compound (A). Provide the mixture.
  • polyisocyanate (A1) examples include tolylene diisocyanate (TDI), diphenylmethane diisocyanate (MDI), MDI oligomer, naphthalene-1,5-diisocyanate, xylylene diisocyanate, hexamethylene diisocyanate (HDI), 4,4-dicyclohexylmethane.
  • the polyisocyanate (A1) is preferably a diisocyanate.
  • R is preferably a linear or branched hydrocarbon group.
  • the hydrocarbon group may be a linear hydrocarbon group in particular.
  • the hydrocarbon group is preferably an aliphatic hydrocarbon group, particularly a saturated aliphatic hydrocarbon group, particularly an alkyl group.
  • the hydrocarbon group preferably has 12 to 30 carbon atoms, and more preferably 16 to 22 carbon atoms.
  • Z is a directly bonded or divalent or trivalent hydrocarbon group having 1 to 5 carbon atoms, regardless of whether it has a linear structure or a branched structure. good.
  • the carbon number of Z is preferably 2 to 4, particularly 2.
  • Z is, -CH 2 CH 2 -, - CH 2 CH 2 CH 2 -, or -CH 2 CH 2 CH 2 CH 2 - is preferably. It is preferable that Z is not a direct bond.
  • the blocking agent (A3) is a compound that masks the isocyanate group of polyisocyanate and suppresses the reaction of the isocyanate group.
  • the blocking agent (A3) include oximes, phenols, alcohols, mercaptans, amides, imides, imidazoles, ureas, amines, imines, pyrazoles, and active methylene compounds.
  • Other examples of the blocking agent (A3) include pyridinol, thiophenols, diketones and esters.
  • the blocked polyisocyanate (blocked isocyanate compound) may be modified with a compound having a hydrophilic group. Oxime, pyrazole, and an active methylene compound are preferable as the blocking agent (A3) because the water repellency and oil repellency are increased. The presence of the blocking agent enhances the water-repellent washing durability.
  • oximes examples include formamide oxime, acetaldoxime, acetone oxime, methyl ethyl keto oxime and cyclohexanone oxime.
  • phenols examples include phenols, which may optionally have at least one (preferably one or two) C 1-10 alkyl groups.
  • phenol include phenol; monoalkylphenol (eg, cresol, ethylphenol, propylphenol, butylphenol, hexylphenol, 2-ethylhexylphenol and octylphenol); and dialkylphenol (eg, diethylphenol, dipropylphenol, dipropylphenol). (Propylcresol, dibutylphenol, di-2-ethylhexylphenol, dioctylphenol and dinonylphenol).
  • additional phenols include styrenated phenols, hydroxybenzoates.
  • alcohols have C 1 -C 30 alkyl group (preferably monovalent) include alcohols (especially alkanol) it is.
  • alcohols include methanol, ethanol, propanol, 1-butanol, sec-butanol, 2-ethyl-1-hexanol, 2-methoxyethanol, 2-butoxyethanol, 2-methoxy-1-propanol and 3-methyl.
  • -2-Penten-4-in-1-all can be mentioned.
  • Specific examples of the mercaptan include butyl mercaptan and dodecyl mercaptan.
  • amides include acetanilide, acetate amide, ⁇ -propiolactam, ⁇ -butyrolactam, ⁇ -valerolactam, ⁇ -caprolactam, laurolactam, stearolactam, N-methyl- ⁇ -. Included are caprolactam and pyrrolidinone.
  • imides include acid imides such as imide maleate and imide succinimide.
  • imidazole examples include imidazole and 2-methylimidazole.
  • urea examples include urea, thiourea and ethylene urea.
  • amines include diphenylamine, aniline, carbazole, diethylamine, dipropylamine and propylethylamine.
  • imine include ethyleneimine and polyethyleneimine.
  • pyrazole examples include 2-methyl-pyrazole, 3-methyl-pyrazole, 4-methyl-pyrazole, 2,4-dimethyl-pyrazole, 2,5-dimethyl-pyrazole, 3,4-dimethyl-pyrazole, 3 , 5-Dimethyl-pyrazole, 4-nitro-3,5-dimethyl-pyrazole, 4-bromo-3,5-dimethyl-pyrazole.
  • active methylene compounds include malonate esters (eg, C 1-30 -alkyl malonic acid esters), acetoacetic esters (eg, C 1-30 -alkyl acetoacetic ester) and acetylacetone.
  • the blocking agent for forming the blocked isocyanate compound is preferably a pyrazole compound or a malonate ester compound, particularly a pyrazole compound.
  • pyrazole compound examples include 2-methyl-pyrazole, 3-methyl-pyrazole, 4-methyl-pyrazole, 2,4-dimethyl-pyrazole, 2,5-dimethyl-pyrazole, and 3,4-dimethyl-pyrazole.
  • Examples thereof include 3,5-dimethyl-pyrazole, 4-nitro-3,5-dimethyl-pyrazole and 4-bromo-3,5-dimethyl-pyrazole.
  • the malonate ester compound is a reaction product (monoester or diester (preferably diester)) of malonic acid and an alcohol (for example, a monohydric alcohol).
  • alcohols have hydrocarbon groups with 1 to 30 carbon atoms attached to hydroxyl groups.
  • the hydrocarbon group is preferably an alkyl group, particularly an alkyl group having 1 to 4 carbon atoms.
  • malonate ester examples include dimethyl malonate, diethyl malonate, dipropyl malonate, dibutyl malonate, methyl malonate, ethyl malonate, propyl malonate and butyl malonate. Diesters are preferred. Preferred specific examples of the malonate ester include dimethyl malonate, diethyl malonate, dipropyl malonate and dibutyl malonate.
  • the alcohol compound (A4) may be monool or polyol.
  • the monool is preferably a compound obtained by adding a C 2 or C 3 alkylene oxide to a starting monoalcohol having 1 to 10 carbon atoms (such as methanol).
  • the polyol may be a polyol having three or more diols and hydroxyl groups.
  • the polyol may be a low molecular weight polyol, a polyether polyol, a polyester polyol, a polyester polycarbonate polyol, or a crystalline or non-crystalline polycarbonate polyol.
  • the alcohol compound (A4) preferably has a hydrophilic group in addition to the hydroxyl group. Hydrophilic groups are not consumed by the urethane reaction. Examples of hydrophilic groups are C 2 or C 3 alkylene oxide groups, amino groups and the like. Since the molecular weight of the urethane compound increases due to cross-linking, the alcohol compound (A4) may consist only of monool.
  • the urethane compound has an R0 group derived from polyisocyanate (A1) and an ⁇ Z (YR) n group derived from a long chain alcohol (A2), and further, a group derived from a blocking agent (A3) and an alcohol. It preferably has a group derived from compound (A4).
  • the total amount of the long-chain alcohol (A2) and the alcohol compound (A4) has an isocyanate index [equivalent ratio of isocyanate groups in polyisocyanate to active hydrogen groups in alcohol] of 2 to 0.5, preferably 1.5.
  • the amount may be up to 0.8, especially 1.2 to 0.9.
  • the molar ratio of the long chain alcohol (A2) to the alcohol compound (A4) is 10: 90-100: 0 or 10: 90-90: 10, for example 20: 80-80: 20, especially 30: 70-70: 30. May be.
  • the amount (equivalent ratio) of the blocking agent (A3) may be 1 to 50 equivalent%, for example 2 to 30 equivalent%, particularly 3 to 20 equivalent%, based on the equivalent of the isocyanate group in the polyisocyanate.
  • the water-based urethane composition contains a urethane compound (A) and water (B).
  • the amount of water (B) may be such that the amount of the urethane compound (A) is 0.1 to 70% by weight, for example, 1 to 50% by weight, based on the aqueous urethane composition.
  • the aqueous urethane composition may contain an organic solvent, and the amount of the organic solvent may be 200 parts by weight or less, for example, 1 to 50 parts by weight, based on 100 parts by weight of water (B).
  • the water-based urethane composition is preferably an aqueous dispersion.
  • the aqueous urethane composition is preferably a self-emulsifying type.
  • the aqueous urethane composition may contain an emulsifier (in an amount of 0.1 to 10 parts by weight with respect to 100 parts by weight of the urethane compound (A)), but preferably does not contain an emulsifier.
  • the urethane compound (A) can be produced by reacting the polyisocyanate (A1) with a long-chain alcohol (A2), and in some cases, an alcohol compound (A4), and if necessary, a blocking agent (A3). ..
  • the aqueous urethane composition can be produced by mixing and reacting polyisocyanate (A1) and long-chain alcohol (A2) in an organic solvent, and then adding water.
  • the aqueous urethane composition is prepared by mixing and reacting a polyisocyanate (A1), a long-chain alcohol (A2) and an alcohol compound (A4) in an organic solvent, and further reacting with a blocking agent (A3), and then reacting. It can be produced by adding water. After adding water, the organic solvent may be removed.
  • the temperature and time for reacting the long chain alcohol (A2) and the alcohol compound (A4) with the polyisocyanate (A1) may be 0 to 60 ° C. and 1 minute to 24 hours.
  • the temperature and time for reacting the blocking agent (A3) may be 30 to 120 ° C. and 1 minute to 24 hours.
  • the urethane compound (A) (and the aqueous urethane composition) can act as a cross-linking agent or an auxiliary agent.
  • the "auxiliary agent” is an agent that assists the performance of the surface treatment agent (an agent that improves water repellency, antifouling property, stain removal property, peelability and / or releasability, especially water repellency and oil repellency. Agents that cause treatment), agents that modify the object to be treated (particularly agents that modify textile products, such as agents that improve the texture of textile products), or agents that assist in stable processing during surface treatment. means. Means.
  • a surface treatment composition can be obtained by mixing the water-based urethane composition and the surface treatment agent.
  • the surface treatment agent mixed with the urethane compound (A) may be any, and may be fluorine-based, silicon-based, urethane-based, acrylic-based, or the like.
  • the surface treatment agent may be in the form of a solution, an emulsion (particularly an aqueous dispersion) or an aerosol, but is preferably an aqueous dispersion.
  • the active ingredient of the surface treatment agent are a fluorine-containing polymer, a silicon-containing polymer, polyurethane, a non-fluorine-non-silicon polymer, and the like.
  • the amount of the urethane compound (A) may be 1 to 100 parts by weight, particularly 5 to 50 parts by weight, based on 100 parts by weight of the active ingredient of the surface treatment agent.
  • the surface treatment composition can be used as a water repellent, an oil repellent, an antifouling agent, a stain remover, a release agent and a mold release agent.
  • the surface treatment composition can be applied to the object to be treated by a conventionally known method.
  • the treatment agent is dispersed in water (and / or an organic solvent), diluted, adhered to the surface of the object to be treated by a known method such as immersion coating, spray coating, foam coating, etc., and dried.
  • the method is adopted. It is preferable to perform curing.
  • the curing temperature may be 60 to 250 ° C., particularly 100 to 200 ° C., and the curing time may be 1 second to 10 minutes, particularly 10 seconds to 3 minutes.
  • the concentration of the urethane-containing fluoropolymer in the treatment liquid to be brought into contact with the base material may be 0.01 to 10% by weight (particularly in the case of dip coating), for example, 0.05 to 10% by weight.
  • the objects to be treated with the surface treatment composition include textile products, stone materials, filters (for example, electrostatic filters), dust masks, fuel cell parts (for example, gas diffusion electrodes and the like). Gas diffusion supports), glass, paper, wood, leather, fur, asbestos, bricks, cement, metals and oxides, ceramic products, plastics, coated surfaces, and plasters.
  • textile products For example, animal and vegetable natural fibers such as cotton, hemp, wool and silk, synthetic fibers such as polyamide, polyester, polyvinyl alcohol, polyacrylonitrile, polyvinyl chloride and polypropylene, semi-synthetic fibers such as rayon and acetate, glass fibers and carbon fibers. , Inorganic fibers such as asbestos fibers, or mixed fibers thereof.
  • the textile product may be in any form such as fiber or cloth.
  • the surface treatment composition can impart desired peelability to the surface of the base material. Therefore, the surface of the base material can be easily peeled off from another surface (another surface on the base material or a surface on another base material).
  • substrates to which the surface treatment composition is applied are textile products (eg, non-woven fabrics and woven fabrics), paper, stone, leather, resin, glass, metal and the like.
  • the equipment is preferably cloth or paper.
  • Surface treatment compositions can be stripped between similar substrates (eg, cloth to cloth, paper to paper), or different substrates (eg, cloth to resin, cloth to metal, paper to cloth, paper to glass). Used for peeling between.
  • the surface treatment composition can be used in the production of an adhesive sheet, a protective material for an adhesive surface of an adhesive tape, a release film, a release paper, a sticky note, and the like.
  • the surface treatment composition can also be used as an internal mold release agent or an external mold release agent.
  • the fluorinated polymer can be applied to fibrous substrates (eg, textiles) by any of the methods known for treating textiles with liquids.
  • the textile is a cloth
  • the cloth may be dipped in the solution, or the solution may be attached or sprayed onto the cloth.
  • the treated textile product is dried and preferably heated at, for example, 100 ° C. to 200 ° C. in order to develop oil repellency.
  • the fluorine-containing polymer may be applied to textile products by a cleaning method, and may be applied to textile products by, for example, a washing application or a dry cleaning method.
  • the textile products to be processed are typically fabrics, which include textiles, knitted fabrics and non-woven fabrics, fabrics and carpets in the form of clothing, but textiles or yarns or intermediate textile products (eg, sliver or It may be blister yarn, etc.).
  • the textile material may be natural fibers (eg, cotton or wool), synthetic fibers (eg, biscorayon or leocell), or synthetic fibers (eg, polyester, polyamide or acrylic fibers), or , A mixture of fibers (eg, a mixture of natural and synthetic fibers).
  • the fluorine-containing polymer of the present disclosure is particularly effective in making cellulosic fibers (for example, cotton or rayon) oleophilic and oil-repellent.
  • the methods of the present disclosure generally make textile products hydrophobic and water repellent.
  • the fibrous substrate may be leather.
  • the fluorinated polymer is aqueous or aqueous at various stages of leather processing to make the leather hydrophobic and oleophobic, for example during the wet processing of the leather or during the finishing of the leather. It may be applied from emulsion to leather.
  • the fibrous substrate may be paper. The fluorinated polymer may be applied to preformed paper or at various stages of papermaking, for example during the drying period of the paper.
  • Treatment means applying a treatment agent (surface treatment composition) to an object to be treated by dipping, spraying, coating or the like.
  • the polymer which is the active ingredient of the treatment agent, permeates the inside of the object to be treated and / or adheres to the surface of the object to be treated.
  • a crosslinked product of the urethane compound adheres to the object to be treated.
  • the shower water repellency test was performed according to the AATCC test method 22-2010.
  • a glass funnel having a volume of at least 250 ml and a spray nozzle capable of spraying 250 ml of water for 20 to 30 seconds are used.
  • the test piece frame is a metal frame having a diameter of 15 cm.
  • Room temperature water (250 mL) is placed in a glass funnel and sprayed onto the test strip sheet (over a period of 25 to 30 seconds).
  • Oil repellency test The oil repellency test was carried out according to the AATCC test method 118-1992.
  • the treated test cloth is stored in a constant temperature and humidity chamber at a temperature of 21 ° C. and a humidity of 65% for 4 hours or more.
  • the test solution used is also stored at a temperature of 21 ° C.
  • the test is conducted in a constant temperature and humidity chamber having a temperature of 21 ° C. and a humidity of 65%. After gently dropping 0.05 ml of the test solution onto the test cloth and leaving it for 30 seconds, if the droplet remains on the test cloth, it is considered that the test solution has passed.
  • the oil repellency is the highest score of the passed test solution, and is evaluated on a 9-point scale of Fail 1, 2, 3, 4, 5, 6, 7 and 8 from a poor oil repellency to a good level.
  • the display "+" after the number indicates that the evaluation is higher than the number, and the display "-" indicates that the evaluation is lower than the number.
  • Water- and oil-repellent washing durability Washing according to the JIS L-0217-103 method is repeated 5 times, 10 times or 15 times, and the subsequent water-repellent and oil-repellent properties are evaluated (HL5, HL10 or HL15).
  • HL0 is the initial water and oil repellency without washing.
  • Synthesis example 1 Put 32.5 g of 1,6-hexamethylene diisocyanate nurate (NCO content 21.8%), 30 g of dipropylene glycol dimethyl ether, and 4.85 g of stearylamide ethyl alcohol in a 300 mL flask and put them in a nitrogen atmosphere from room temperature with stirring. The internal temperature was raised to 85 ° C., 0.020 g of dibutyltin dilaurate was added, and the mixture was stirred for 2 hours. Then, 5 g of polyethylene glycol monomethyl ether (molecular weight 1000) was added and stirred for 3 hours, and 14.3 g of dimethylpyrazole was further added and stirred for 2 hours.
  • Comparative synthesis example 1 Put 32.5 g of diphenyldiisocyanate (NCO content 21.8%) and 30 g of dipropylene glycol dimethyl ether in a 300 mL flask, raise the internal temperature from room temperature to 85 ° C. under stirring while creating a nitrogen atmosphere, and add 0.020 g of dibutyltin dilaurate. It was put in and stirred for 2 hours. Then, 5 g of polyethylene glycol monomethyl ether (molecular weight 1000) was added and stirred for 3 hours, and 14.3 g of methyl ketooxime was further added and stirred for 2 hours. The disappearance of NCO groups was confirmed by IR, and the mixture was cooled to room temperature. After cooling, water at 40 ° C. was added under strong stirring, and the mixture was stirred for 10 minutes to produce an aqueous dispersion having a solid content of 20%.
  • NCO content 21.8% dipropylene glycol dimethyl ether
  • Comparative synthesis example 2 In a 300 mL flask, put 32.5 g of a nurate form of 1,6-hexamethylene diisocyanate (NCO content 21.8%), 30 g of dipropylene glycol dimethyl ether, and 4.05 g of stearyl alcohol, and put them in a nitrogen atmosphere under stirring at room temperature to 85 ° C. The internal temperature was raised to 0.020 g of dibutyltin dilaurate and stirred for 2 hours. Then, 5 g of polyethylene glycol monomethyl ether (molecular weight 1000) was added and stirred for 3 hours, and 14.3 g of dimethylpyrazole was further added and stirred for 2 hours.
  • NCO content 21.8% 1,6-hexamethylene diisocyanate
  • dipropylene glycol dimethyl ether 1,6-hexamethylene diisocyanate
  • 4.05 g of stearyl alcohol stearyl alcohol
  • VCM vinyl chloride
  • azo group-containing water-soluble initiator 0.4 g of an azo group-containing water-soluble initiator is added, and the mixture is reacted at 60 ° C. for 20 hours to carry out an aqueous dispersion of a fluorine-containing polymer.
  • Fluorine-containing water-repellent oil-repellent agent was obtained.
  • the composition of the polymer was almost the same as the composition of the charged monomer.
  • Example 1 The fluorine-containing water repellent oil repellent obtained in Synthesis Example 2 (water and oil repellent as an active ingredient a fluorinated acrylic polymer having a C 6 perfluoroalkyl group) and 4% by diluting with water, in Synthesis Example 1
  • the obtained aqueous dispersion was added so as to be 1%, and the mixture was uniformly stirred.
  • Ten nylon woven fabrics (500 mm x 200 mm) and cotton cloth (500 mm x 200 mm) were continuously immersed in this test solution, passed through a mangle, and treated with a pin tenter at 170 ° C. for 1 minute. After that, each of the nylon woven cloth and the cotton cloth was subjected to a shower water repellency test, an oil repellency test and a washing durability test thereof.
  • Table A The results are shown in Table A.
  • Comparative Examples 1 and 2 The procedure is the same as that of Example 1 except that the aqueous dispersion obtained in Comparative Synthesis Example 1 (Comparative Example 1) or Comparative Synthesis Example 2 (Comparative Example 2) is used instead of the aqueous dispersion obtained in Synthesis Example 1. Was repeated. The results are shown in Table A.
  • Example 2 The same procedure as in Example 1 was repeated except that the aqueous dispersion of the non-fluorine polymer obtained in Synthesis Example 3 was used instead of the aqueous dispersion of the fluorine-containing polymer obtained in Synthesis Example 2. The results are shown in Table A.
  • Comparative Examples 3 and 4 The procedure is the same as that of Example 2 except that the aqueous dispersion obtained in Comparative Synthesis Example 1 (Comparative Example 3) or Comparative Synthesis Example 2 (Comparative Example 4) is used instead of the aqueous dispersion obtained in Synthesis Example 1. Was repeated. The results are shown in Table A.
  • the urethane composition of the present disclosure can be used as a cross-linking agent or an auxiliary agent.
  • the urethane composition of the present disclosure can be used together with a surface treatment agent, can enhance the efficacy of the surface treatment agent, and can improve the durability of the efficacy (particularly the washing durability).

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Medicinal Chemistry (AREA)
  • Health & Medical Sciences (AREA)
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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006038466A1 (ja) 2004-10-05 2006-04-13 Adeka Corporation 水分散型ポリウレタン組成物
JP2013511574A (ja) * 2009-11-20 2013-04-04 ダイキン工業株式会社 含フッ素重合体および処理剤
JP2014210882A (ja) 2013-04-19 2014-11-13 旭化成ケミカルズ株式会社 ブロックポリイソシアネート組成物、水分散体、繊維処理剤組成物及び布帛

Family Cites Families (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL266256A (https=) * 1960-06-25
US4277380A (en) * 1979-03-29 1981-07-07 Textron, Inc. Water-dispersible urethane polymers and aqueous polymer dispersions
JPS5840134A (ja) * 1981-09-04 1983-03-09 Mitsubishi Petrochem Co Ltd 疎水性物質の水性分散液の製造方法
US5777023A (en) * 1996-10-01 1998-07-07 Union Camp Corporation Diamidediurethanes and hot-melt printing therewith
WO2000063269A1 (en) * 1999-04-19 2000-10-26 Inolex Investment Corporation Polyurethane foam cell opening agents and methods for making foam using the same
CA2286446C (en) * 1999-10-15 2007-01-09 American Dye Source, Inc. Hot melt ink compositions for inkjet printing applications
KR20020092704A (ko) * 2001-06-05 2002-12-12 닛폰 폴리우레탄 고교 가부시키가이샤 적층 접착제용 폴리이소시아네이트 경화제 및 그 제조방법
DE10325094B4 (de) * 2003-06-03 2006-02-16 Rudolf Gmbh & Co. Kg Chemische Fabrik Zubereitungen für die öl- und wasserabweisende Ausrüstung von Flächengebilden und deren Anwendung
JP4563729B2 (ja) 2003-09-04 2010-10-13 東京エレクトロン株式会社 プラズマ処理装置
JP5634012B2 (ja) * 2008-02-27 2014-12-03 株式会社Adeka 水系ポリウレタン樹脂組成物及びそれを塗布してなる被塗物
NZ591598A (en) * 2008-11-14 2012-08-31 Du Pont Particle-modified fluoropolymers for imparting surface properties to substrates wherein the particle-modified fluoropolymers impart oil repellency, water repellency and soil resistance properties
WO2010150699A1 (ja) * 2009-06-24 2010-12-29 旭硝子株式会社 撥水撥油剤および撥水撥油剤組成物
CN105339408B (zh) * 2013-06-27 2018-09-21 旭化成株式会社 多异氰酸酯组合物以及其的制造方法、封端多异氰酸酯组合物以及其的制造方法、树脂组合物、固化性树脂组合物、以及固化物
FR3015489B1 (fr) * 2013-12-20 2016-11-25 Inst Des Corps Gras Etudes Et Rech Techniques - Iterg Procede de preparation de dispersions de polyurethane par polymerisation en mini-emulsion
CN104711854B (zh) * 2015-03-23 2016-09-21 苏州陈恒织造有限公司 一种精梳棉与大豆蛋白纤维混纺面料用整理剂
EP3320011B1 (de) * 2015-07-08 2019-09-25 BYK-Chemie GmbH Urethan- und harnstoffgruppenhaltige reaktionsprodukte
US20190100615A1 (en) * 2016-03-29 2019-04-04 Asahi Kasei Kabushiki Kaisha Blocked polyisocyanate composition, one-component coating composition, coating film, and coated article
JP6682996B2 (ja) * 2016-04-28 2020-04-15 凸版印刷株式会社 感熱転写記録媒体
DE102016212443A1 (de) 2016-07-07 2018-01-11 Rudolf Gmbh Zubereitungen als Hydrophobierungsmittel
CN106753523A (zh) * 2016-11-18 2017-05-31 东营明德石油科技有限公司 一种广谱高效原油破乳剂的合成方法
JP6908193B2 (ja) * 2018-06-27 2021-07-21 Dic株式会社 フッ素系共重合体、滑水性表面改質剤、硬化性樹脂組成物、及び滑水性塗膜
CN109295730A (zh) * 2018-08-22 2019-02-01 新天地纺织印染（嘉兴）有限公司 紫外线阻隔剂及应用该紫外线阻隔剂的尼龙皮肤衣面料抗紫外处理工艺

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006038466A1 (ja) 2004-10-05 2006-04-13 Adeka Corporation 水分散型ポリウレタン組成物
JP2013511574A (ja) * 2009-11-20 2013-04-04 ダイキン工業株式会社 含フッ素重合体および処理剤
JP2014210882A (ja) 2013-04-19 2014-11-13 旭化成ケミカルズ株式会社 ブロックポリイソシアネート組成物、水分散体、繊維処理剤組成物及び布帛

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of EP4137479A4

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EP4137479A4 (en) 2024-04-24
JP7469695B2 (ja) 2024-04-17
KR102822550B1 (ko) 2025-06-20
EP4137479A1 (en) 2023-02-22

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