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WO2007080900A1 - Composition de resine de polyurethane pour tissu etanche permeable a l’humidite et tissu etanche permeable a l’humidite - Google Patents

Composition de resine de polyurethane pour tissu etanche permeable a l’humidite et tissu etanche permeable a l’humidite Download PDF

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Publication number
WO2007080900A1
WO2007080900A1 PCT/JP2007/050184 JP2007050184W WO2007080900A1 WO 2007080900 A1 WO2007080900 A1 WO 2007080900A1 JP 2007050184 W JP2007050184 W JP 2007050184W WO 2007080900 A1 WO2007080900 A1 WO 2007080900A1
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WO
WIPO (PCT)
Prior art keywords
moisture
polyurethane resin
permeable waterproof
fabric
layer
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/JP2007/050184
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English (en)
Japanese (ja)
Inventor
Yutaka Hayashi
Junsho Kanenori
Yukichi Izumi
Yoshio Kobayashi
Tomonori Adachi
Hiroyuki Ogawa
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.)
Komatsu Seiren Co Ltd
Sanyo Chemical Industries Ltd
Original Assignee
Komatsu Seiren Co Ltd
Sanyo Chemical Industries Ltd
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Filing date
Publication date
Application filed by Komatsu Seiren Co Ltd, Sanyo Chemical Industries Ltd filed Critical Komatsu Seiren Co Ltd
Publication of WO2007080900A1 publication Critical patent/WO2007080900A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • C08G18/28—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
    • C08G18/4804—Two or more polyethers of different physical or chemical nature
    • C08G18/4808—Mixtures of two or more polyetherdiols
    • 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
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • 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
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
    • 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
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4854—Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group
    • 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
    • C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
    • C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
    • C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
    • C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
    • C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
    • 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

Definitions

  • Polyurethane resin composition for moisture-permeable waterproof fabric and moisture-permeable waterproof fabric for moisture-permeable waterproof fabric and moisture-permeable waterproof fabric
  • the present invention relates to a polyurethane resin composition for moisture-permeable waterproof fabric and a moisture-permeable waterproof fabric.
  • a moisture-permeable waterproof fabric having a nonporous polyurethane resin is dried by coating the fiber fabric with a moisture-permeable polyurethane resin solution, or drying after coating the release paper with the moisture-permeable polyurethane resin solution. Then, the obtained polyurethane resin film is manufactured by adhering to a fiber cloth with an adhesive (see, for example, Patent Document 1 and Patent Document 2). Solvents such as dimethylformamide (DMF), toluene, and methylethylketone (MEK), which are good solvents for polyurethane resins, are used as solvents for the polyurethane resin solutions used in these products, producing moisture-permeable waterproof fabrics.
  • DMF dimethylformamide
  • MEK methylethylketone
  • Patent Document 1 Japanese Patent Application Laid-Open No. 64-62320
  • Patent Document 2 JP-A-3-203920
  • Patent Document 3 Japanese Patent Laid-Open No. 2002-69370
  • Patent Document 4 Japanese Unexamined Patent Application Publication No. 2004-300178
  • the coating film processability (hereinafter referred to as film forming property may be smaller) than in the case of a polyurethane resin using a conventional solvent.
  • the moisture-permeable waterproof fabric that can be obtained with the same meaning) is not sufficient in water resistance (hereinafter sometimes referred to as waterproof), moisture permeability and heat resistance. The current situation is that it has not been put to practical use.
  • An object of the present invention is to provide a moisture permeable waterproof fabric having a coating strength equal to or higher than that of a polyurethane resin using a conventional solvent that has a small load on the work environment hygiene and exhaust treatment.
  • An object of the present invention is to provide a polyurethane resin composition having excellent water resistance, moisture permeability and heat resistance.
  • the present inventors can design a hydrophilic polyurethane resin that is soluble in an alcohol solvent and that has a performance equal to or higher than that of a polyurethane resin using a conventional solvent. As a result, they have reached the present invention.
  • the present invention provides a moisture-permeable waterproof fabric comprising an alcoholic solution of a hydrophilic polyurethane resin (A) having an oxyethylene group content of 10 to 80% by weight in the resin and a polyisocyanate (B) force.
  • A hydrophilic polyurethane resin
  • B polyisocyanate
  • the present invention relates to a polyurethane resin composition.
  • the alcohol in the alcohol solution is one or more alcohols selected from the group consisting of secondary and tertiary alcohols.
  • (A) is formed from a polymer diol (C) having an oxyethylene group-containing polymer diol (C1) as essential components, a diisocyanate (D), and a chain extender (E).
  • C polymer diol
  • D diisocyanate
  • E chain extender
  • the content of the oxyethylene group in (C1) is at least 3
  • the equivalent ratio of (D) and (C): (D) / (C) is (1.3 to 10) Zl.
  • an embodiment is an equivalent ratio of (D) and [(C) + ( ⁇ )]: (D) / [(C) + ( ⁇ )]
  • (D) is an alicyclic diisocyanate and ( ⁇ ) is an alicyclic diamine.
  • the polyisocyanate ( ⁇ ) is a urethane-modified product of hexamethylene diisocyanate, a burette-modified product, an isocyanurate-modified product, or an isocyanurate-modified product of isophorone diisocyanate.
  • hydrophilic monools or Is one or more selected from the group consisting of denatured products reacted with diol.
  • it is 3 to 60% by weight based on the weight of the (B) specific force (A).
  • the composition further comprises one or more additives selected from the group consisting of a weather resistance stabilizer, a heat resistance stabilizer, a colorant, an inorganic filler, an organic modifier, and a penetration improver. Is also preferred.
  • the present invention also provides:
  • a moisture permeable waterproof fabric A moisture permeable waterproof fabric
  • the present invention also relates to a moisture-permeable waterproof fabric characterized in that the nonporous layer is a polyurethane resin layer formed by applying the composition.
  • the moisture-permeable waterproof fabric preferably further has an adhesive layer at least at a part between the fiber fabric and the nonporous layer.
  • the present invention also provides
  • a second fiber fabric and
  • Non-porous layer of polyurethane resin formed at least in part between the first fiber fabric and the second fiber fabric
  • a moisture permeable waterproof fabric having
  • the present invention also relates to a moisture-permeable waterproof fabric characterized in that the nonporous layer is a polyurethane resin layer formed from the composition.
  • the moisture-permeable waterproof fabric further adheres to at least a part of at least one of the first fiber fabric and the nonporous layer, or the second fiber fabric and the nonporous layer. It is preferable to have a layer.
  • the present invention also provides:
  • Release paper A non-porous layer of polyurethane resin comprising the above composition, and
  • the present invention also relates to a method for producing a moisture-permeable waterproof fabric characterized in that after the fiber fabric surface is bonded to the surface on the adhesive layer side of the laminate obtained by laminating layers in this order, the release paper is peeled off.
  • the laminate comprises a step of coating the release composition on the release paper to form a non-porous layer of polyurethane resin, and
  • the present invention provides
  • the present invention also relates to a method for imparting moisture permeability and waterproofness to a fiber fabric, characterized in that a nonporous layer formed by applying the above composition is provided on at least a part of at least one side of the fiber fabric.
  • the present invention provides:
  • the present invention also relates to the use of the composition as the nonporous layer in a moisture permeable waterproof fabric having a polyurethane resin nonporous layer on at least a part of at least one side of the fiber fabric.
  • the alcohol solution of the hydrophilic polyurethane resin (A) having an oxyethylene group content of 10 to 80% by weight and soluble in alcohol is composed of a polymer diol (C), diisocyanate (D), and chain extension.
  • a polyurethane resin solution comprising a polyurethane resin comprising an agent (E) and an alcohol solvent (F).
  • a substance that dissolves 10 g or more per 100 g of alcohol is judged to be soluble.
  • the polymer diol (C) is preferably a polymer diol containing an oxyethylene group-containing polymer diol (C1) as an essential component from the viewpoint of moisture permeability.
  • a polymer diol (C2) other than (C1) can be used in combination as long as the moisture permeability is not inhibited.
  • (C2) is usually 60% by weight or less based on the weight of (C). From the viewpoint of wettability, it is preferably 5 to 50% by weight.
  • Examples of (C2) include polyether diols (C21) other than (C1), polyester diols (C
  • the content is preferably at least 30% by weight, more preferably 40 to 100% by weight, based on the weight of (C1).
  • Examples of (C1) include polyoxyethylene glycol (hereinafter abbreviated as PEG), polyoxyethyleneoxypropylene block copolymerized diol (hereinafter abbreviated as PEPG), polyoxyethyleneoxytetramethylene block copolymerized diol, and ethylene oxide.
  • Random copolymerization of ethylene and propylene oxide Random copolymerization diol of ethylene oxide and tetrahydrofuran; Ethylene glycol mononole, propylene glycolenole, 1,4_butanediole, 1,6_hexamethylene glycol, bis Ethylene oxide adducts of low molecular weight Daricol, such as (hydroxymethyl) cyclohexane, 4, 4, 1-bis (2-hydroxyethoxy) -diphenylpropane; number average molecular weight [hereinafter abbreviated as Mn.
  • Mn number average molecular weight
  • Condensed polyether obtained by reacting PEG of 1,000 or less and dicarboxylic acid [carbon number (hereinafter abbreviated as C) 2 to 12, such as succinic acid, adipic acid, sebacic acid, terephthalic acid, isophthalic acid, etc.] Ester diols; and mixtures of two or more of these.
  • PEG, PEPG, and polyoxyethyleneoxytetramethylene block copolymer diol are preferable from the viewpoint of moisture permeability, and PEG and PEPG are particularly preferable.
  • Mn of (C1) is preferably 500 to 20,000, more preferably 700 to 15,000 from the viewpoint of moisture permeability and coating strength.
  • polyoxypropylene glycol include polyoxytetramethylene glycol (hereinafter abbreviated as PTMG), polyoxypropyleneoxytetramethylene block copolymerized diol, and the like, and mixtures of two or more thereof.
  • PTMG polyoxytetramethylene glycol
  • polyoxypropyleneoxytetramethylene block copolymerized diol include polyoxypropylene glycol, polyoxytetramethylene glycol (hereinafter abbreviated as PTMG), polyoxypropyleneoxytetramethylene block copolymerized diol, and the like, and mixtures of two or more thereof.
  • polyester diol (C22) examples include polyethylene adipate, polybutylene adipate, poly 2,2-dimethyltrimethylene adipate, poly 3-methylpentamethylene adipate, polyhexamethylene adipate, polystrength prolatatone diol, and 2 A mixture of seeds or more can be mentioned.
  • Examples of the polycarbonate diol (C23) include polyhexamethylene carbonate dial.
  • Preferred Mn of (C2) is the same as Mn of (CI).
  • the diisocyanate (D) used in the hydrophilic polyurethane resin solution (A) in the present invention is, for example, C (the same applies hereinafter except for carbon in the NCO group) 6 to: 12 aliphatic diisocyanate, C6 ⁇ : 15 alicyclic diisocyanates, C8 ⁇ : 12 araliphatic diisocyanates, C6-30 aromatic diisocyanates and mixtures of two or more thereof.
  • aliphatic diisocyanate examples include hexamethylene diisocyanate (HDI), dodecamethylene diisocyanate, 2,2,4_trimethylhexamethylene diisocyanate, lysine diisocyanate. 1, 3, 6-trimethylhexamethylene diisocyanate and the like.
  • HDI hexamethylene diisocyanate
  • dodecamethylene diisocyanate 2,2,4_trimethylhexamethylene diisocyanate
  • lysine diisocyanate 1, 3, 6-trimethylhexamethylene diisocyanate and the like.
  • alicyclic diisocyanate examples include isophorone diisocyanate (hereinafter abbreviated as IPDI), dicyclohexylmethane 4,4'-diisocyanate, 1,4-cyclohexanediisocyanate, methylcyclohexane. 1,2,4 diisocyanate, 1,4 bis (2-isocyanatoethyl) cyclohexane and the like.
  • IPDI isophorone diisocyanate
  • dicyclohexylmethane 4,4'-diisocyanate 1,4-cyclohexanediisocyanate
  • methylcyclohexane methylcyclohexane
  • 1,2,4 diisocyanate 1,4 bis (2-isocyanatoethyl) cyclohexane and the like.
  • araliphatic diisocyanate examples include p- or m-xylylene diisocyanate, ⁇ , ⁇ '-tetramethylxylylene diisocyanate, and the like.
  • aromatic diisocyanate examples include 1, 3— or 1, 4 phenylene diisocyanate, 2, 4 and / or 2, 6 tolylene diisocyanate (hereinafter abbreviated as TDI), 2, 4 ′. — And ⁇ or 4,4'-diphenylmethane diisocyanate (hereinafter abbreviated as MDI), naphthalene-1,5-diisocyanate, 3,3'-dimethyldiphenylmethane-1,4'-diisocyanate, etc. Is mentioned.
  • alicyclic diisocyanates are preferred among these, and IPDI is particularly preferred.
  • Examples of the chain extender (E) include low molecular diols [C2 to 10 such as ethylene glycol (hereinafter abbreviated as EG), propylene glycol, 1,4-butanediol (hereinafter abbreviated as BD), etc.], Aliphatic diamines (C2-6, such as ethylene diamine), alicyclic diamines (C5-15, such as 4,4'-diaminocyclohexane, isophorone diamine (hereinafter abbreviated as IPDA), 4, 4'-diamino Dicyclohexylmethane (hereinafter abbreviated as DADCHM)], aromatic diamines (C6 to: 15, for example, 4, 4, monophenylenediamine, 4, 4'-diaminodiphenylmethane) Etc.), hydrazine and the like, and mixtures of two or more thereof. Of these, low molecular diols and alicyclic diamine
  • Examples of the alcohol solvent (F) include primary alcohols (Cl-10, such as methanol, ethanol, n_propinoreanololeconole, n- butinoreanoreconole, ethyleneglycolenomonomethyl ether).
  • Ethylene glycol monoethyl ether, etc. secondary alcohol [C3 to: 10, for example, isopropyl alcohol (hereinafter abbreviated as IPA), sec-butyl alcohol, propylene glycol monomethyl ether (hereinafter abbreviated as MPG), propylene glycol mono Examples thereof include propyl ether (hereinafter abbreviated as PPG), tertiary alcohol [C4-10, such as t-butyl alcohol (hereinafter abbreviated as t BA)], and mixtures of two or more of these.
  • IPA isopropyl alcohol
  • MPG propylene glycol monomethyl ether
  • PPG propylene glycol mono
  • PPG propyl ether
  • t BA tertiary alcohol
  • one alcohol selected from the group consisting of secondary alcohols and tertiary alcohols, and a mixture of two or more thereof are particularly preferable.
  • the oxyethylene group content of the hydrophilic polyurethane resin (A) is 10% by weight or more, preferably 20% by weight or more, more preferably 25% from the viewpoint of moisture permeability based on the total weight of (A). From the viewpoint of the strength of the film (coating film), it is 80% by weight or less, preferably 70% by weight or less, and more preferably 65% by weight or less.
  • the oxyethylene group content can be calculated as follows:
  • the equivalent ratio of each component of diisocyanate (D), polymer diol (C) and chain extender (E) is (D) / (C).
  • the equivalence ratio is usually preferably (1.3 to 10) Zl, more preferably (1.5 to 5) from the viewpoint of heat resistance and the modulus (texture) of the coating film (nonporous layer, the same shall apply hereinafter) described later. ) / 1.
  • the equivalent ratio of (D) to [(C) + (E)] [(D) / [(C) + (E)]] is usually from the viewpoint of molecular weight of polyurethane resin and practically useful physical properties. It is preferably (0.9 to: 1.
  • (A) can be obtained by reacting (D), (C) and (E) in the above equivalent ratio.
  • (A) reaches the target molecular weight and there is an NCO group at both ends or at one end, block the NC ⁇ group with alkanolamine or low-molecular dallicol, which will be described later, at both ends. OH group is introduced.
  • Mn of hydrophilic polyurethane resin (A) [Mn of polyurethane resin is measured by gel permeation chromatography (GPC) method. ] Is preferably from 5,000 to 50,000, particularly preferably ⁇ or 10,000 to 300 to 300 from the viewpoint of the strength of the coating film described later and the viscosity, coating properties and uniform coating film of the polyurethane resin solution described later. , 000.
  • the measurement by the gel permeation chromatography (GPC) method is not particularly limited.
  • HLC-8220 manufactured by Tosohichi Corporation
  • the column temperature is 40 ° C.
  • the hydrophilic polyurethane resin (A) can be produced by a usual method, for example, a one-shot method in which a diisocyanate (D), a polymer diol (C) and a chain extender (E) are reacted simultaneously. , (D) and polymer diol (C) are reacted first, and then (E) is reacted successively.
  • the production of (A) can be carried out in the presence or absence of a solvent.
  • the alcohol solvent (F) is a suitable solvent when used in the presence of a solvent.
  • the production of (A) can be carried out by a production apparatus usually employed in the industry. If a solvent is not used, a kneader or an etrustruder can be used.
  • the hydrophilic polyurethane resin (A) produced in this manner is 30% by weight (resin content).
  • the solution viscosity measured as an IP A solution is usually 1 to 1,000 Pa's / 20 ° C. Like It is 3 ⁇ 300Pa's / 20. C.
  • the amount of the solvent in the alcohol solution of (A) is usually 5% of the polyurethane resin.
  • the amount is -50% by weight, preferably 10-40% by weight.
  • the reaction temperature is the same as that usually used for the polyurethane reaction, and usually 20 to 100 ° C when a good solvent is used. Usually 20 ⁇ 220 ° C.
  • a catalyst usually used in the polyurethane reaction for example, an amine catalyst (triethylamine, triethylenediamine, etc.) or a tin catalyst (dibutyltin dilaurate, etc.). Can be used.
  • an amine catalyst triethylamine, triethylenediamine, etc.
  • a tin catalyst dibutyltin dilaurate, etc.
  • a monohydric alcohol, monohydric amine, low-molecular glycol or alkanolamine can be used as a reaction terminator in order to complete the reaction if necessary.
  • Examples of monohydric alcohols include ethanol and butanol;
  • Examples of monohydric amines include dialkylamines such as jetylamine and dibutylamine;
  • Examples of low molecular weight darikols include ethylene darcol, propylene glycol, and 1,4 butanediol;
  • Examples include monoethanolamine and diethanolamine.
  • alkanolamine is preferred from the viewpoint of reactivity.
  • the hydroxyl value of (A) having O as an end group is preferably 0.5 to 25 (mgKOH / g. In the following, only numerical values are described), more preferably 1 to 20, more preferably 1.5 to 15.
  • the polyisocyanate (B) in the present invention for example, the above-mentioned diisocyanate (D), a urethane-modified product obtained by reacting the diisocyanate (D) with trimethylolpropane (TMP) at a molar specific force 3 ⁇ 4Zl
  • TMP trimethylolpropane
  • HDI, IPDI, or a modified product obtained by reacting TDI with TMP for example, trade names “WB40-100”, “Deyuranate P-301-75E” (all manufactured by Asahi Kasei Kogyo Co., Ltd.), “Coronate HL” (manufactured by Nippon Polyurethane Co., Ltd.), etc.
  • a molar specific force of 3 ⁇ 4 / 1 for example, HD or a modified product obtained by reacting IPDI with water.
  • “Sumijoule N-100” manufactured by Sumitomo Bayer Urethane Co., Ltd.
  • “Deyuranate 24A-100” manufactured by Asahi Kasei Kogyo Co., Ltd.
  • Isocyanurate modified [For example, HD pods or IPD pods or TDI trimers.
  • the product name “Midilleur N_3500” (manufactured by Sumitomo Bayer Urethane Co., Ltd., “Deyuranate TPA-100” (manufactured by Asahi Kasei Kogyo Co., Ltd.), etc.), modified products obtained by reacting these modified products with hydrophilic monools or diols
  • hydrophilic monools or diols for example, a molar ratio of the above urethane-modified product, burette-modified product, or isocyanurate-modified product and a hydrophilic monool obtained by adding 5 to 100 moles of ethylene oxide to an alcohol such as methanol or ethanol is 1 / (0.5 ⁇ : 1.
  • modified product, urethane modified product, burette modified product, isocyanurate modified product or IPDI isocyanurate modified product and hydrophilic diol such as PEG were reacted at a molar ratio of 2/1.
  • Modified body etc. dimer of the above modified body [for example, molar ratio of the above urethane modified body or burette modified body or isocyanurate modified body to EG, BD is 2/1 Reacted modified products, etc.] trimers of the above modified products [for example, HDI urethane modified product, burette modified product, isocyanurate modified product or IPDI isocyanurate modified product and TMP are reacted at a molar ratio of 3/1. And the like, and mixtures of two or more of these.
  • urethane-modified HDI burette-modified
  • isocyanurate-modified IPDI
  • IPDI isocyanurate modified products, modified products obtained by reacting these modified products with hydrophilic monool or diol, and mixtures of two or more of these.
  • the ratio of the hydrophilic polyurethane resin (A) and the polyisocyanate (B) used is less than 100 parts by weight of the resin component of (A).
  • the isocyanate (B) is preferably 3 to 60 parts by weight, more preferably 4 to 50 parts by weight, and particularly preferably 5 to 35 parts by weight. If it is 3 parts by weight or more, the coating film strength and heat resistance are sufficient, and if it is 60 parts by weight or less, the texture is good.
  • hydrophilic polyurethane resin (A) various stabilizers for improving weather resistance, heat deterioration, etc., if necessary [weather resistance stabilizer (antioxidant, ultraviolet absorber, light stabilizer, etc.), heat resistance Stabilizer (Phosphorus compound heat stabilizer, Lataton compound heat stabilizer, etc.)], Colorant (Titanium oxide, Carbon black, etc.), Inorganic filler (Calcium carbonate, Silica, etc.), Organic modifier (AS resin, PVC, etc.) Resin, cellulose, protein, etc.) and a fiber fabric (described later) having a porous membrane (polytetrafluoroethylene porous membrane, polyurethane resin porous membrane, etc.) on at least one side.
  • Other additive agents such as penetration enhancers (butanol, toluene, etc.) for the purpose of improving adhesive strength can be contained.
  • the polyurethane resin composition for a moisture-permeable waterproof fabric of the present invention may be a mixture of the hydrophilic polyurethane resin (A), the polyisocyanate (B), other additives and the like only by ordinary stirring or mixing. It can be obtained by merging with a device (ball mill, kneader, sand blaster, roll mill, etc.), or by slipping.
  • the present invention provides a fiber fabric
  • a moisture permeable waterproof fabric A moisture permeable waterproof fabric
  • Another aspect of the present invention provides:
  • a second fiber fabric and
  • Non-porous layer of polyurethane resin formed at least in part between the first fiber fabric and the second fiber fabric
  • a moisture permeable waterproof fabric having
  • a moisture-permeable waterproof fabric characterized in that the nonporous layer is a polyurethane resin layer formed from the composition.
  • the fiber fabric for example, all fabrics made of natural fibers or synthetic fibers can be used. Specific examples include fabrics such as cotton, suf, polyester, nylon, and acrylic, and blends of two or more of these, mixed fibers, and interwoven fabrics. Examples of the form of the fabric include a woven fabric, a knitted fabric, a nonwoven fabric, and a raised fabric. Further, it may be a laminated base material having a porous film of a polyurethane resin or polytetrafluoroethylene on at least one surface of the fiber fabric. These fiber fabrics may be subjected to water repellent treatment with silicon resin, fluorine resin or the like in order to prevent excessive penetration of the coating liquid or adhesive into the fiber fabric.
  • the nonporous layer is formed from the polyurethane resin composition.
  • a method for forming the nonporous layer is not particularly limited, and a known method can be employed.
  • a direct coating method in which a resin composition (polyurethane resin composition) is directly applied to a fiber fabric, or a nonporous layer of resin is formed by applying the resin composition on a release paper to form a nonporous layer of resin.
  • a dry laminating method in which an adhesive is applied on the porous layer, the fiber fabric and the nonporous layer are bonded together, and the release paper is peeled off.
  • a dry lamination method is preferable.
  • the present invention is a.
  • a non-porous layer of polyurethane resin comprising the above composition, and
  • the present invention also relates to a method for producing a moisture-permeable waterproof fabric characterized in that after the fiber fabric surface is bonded to the surface on the adhesive layer side of the laminate obtained by laminating layers in this order, the release paper is peeled off.
  • the laminate includes a step of coating the release composition on the release paper to form a non-porous layer of polyurethane resin, and
  • a coating solution is prepared on a release paper using the polyurethane resin composition of the present invention and an alcohol solvent.
  • surfactants pigments such as titanium oxide and carbon black, inorganic or organic fine particles such as calcium carbonate, silica, cellulose, and protein may be added to the coating solution.
  • the coating liquid is applied onto the release paper using a knife coater, pipe coater, bar coater or the like. Then, it is dried at a temperature of about 100 ° C. to about 160 ° C. for about 30 seconds to 5 minutes using a dryer such as an air oven to form a non-porous layer of polyurethane resin. Also, if necessary, adjust the slit clearance of the coater when applying the coating liquid, and repeat the application and drying to make the nonporous layer the desired thickness.
  • an adhesive is applied to the obtained nonporous layer to form an adhesive layer.
  • the adhesive include known adhesives such as a two-component polyurethane resin, but a hot-melt resin such as a moisture curable resin that does not use an organic solvent is preferable from the viewpoint of the global environment and working environment.
  • a gravure coater for the adhesive, use a gravure coater, knife coater, pipe coater, bar coater, etc., and apply it to the entire nonporous layer in the form of a whole surface, a line, a dot, etc., and dry as necessary.
  • the fiber fabric surface is bonded to the coated surface of the adhesive layer.
  • the laminated body after pasting has a structure in which a fiber fabric, an adhesive layer, and a nonporous layer are sequentially laminated.
  • the obtained laminate is subjected to thermocompression bonding at a temperature of 80 ° C to 160 ° C, and if necessary, aged at 30 ° C to 110 ° C for 20 to 100 hours.
  • a moisture-permeable waterproof fabric in which a nonporous layer made of polyurethane resin is formed in this order on one side of the fiber fabric via an adhesive layer is obtained.
  • the thickness of the nonporous layer is preferably 5 111 to 100/1 111 from the viewpoint of water resistance.
  • the obtained moisture-permeable waterproof fabric may be subjected to a water-repellent treatment using a fluorine-based or silicon-based water-repellent agent.
  • the above polyurethane resin composition is directly applied to one side of a fiber fabric by a direct coating method, and another fiber fabric is immediately bonded and thermocompression bonded, or heated and dried after the direct coating.
  • a nonporous layer of polyurethane resin is also formed between the fiber fabric and the fiber fabric by a method in which a nonporous layer is formed and then an adhesive is applied to the surface and another fiber fabric is bonded. Can be obtained.
  • the following method can also be employed. First, as described above, a non-porous layer is formed on a release paper, and an adhesive is applied on the non-porous layer to form a first laminate having an adhesive layer formed thereon.
  • the above polyurethane resin composition is directly coated on one side of another fiber fabric, and heated and dried to form a second laminate having a nonporous layer.
  • the release paper is peeled off to thereby remove the nonporous layer.
  • a desired moisture-permeable waterproof fabric having a fiber fabric between the nonporous layer and the nonporous layer can be obtained.
  • the moisture-permeable waterproof fabric obtained may be subjected to water repellent treatment with the water repellent as necessary.
  • a nonporous layer is formed on a release paper in the same manner as described above, and an adhesive is applied on the nonporous layer to form an adhesive layer. Create two sets of this laminate.
  • the desired moisture-permeable waterproof fabric can be obtained by sandwiching the fiber fabric with the adhesive layer of the two sets of laminates and thermocompression bonding.
  • the following method can also be employed.
  • the polyurethane resin composition is directly applied to both sides of a fiber fabric by a direct coating method, and heated and dried to form a nonporous layer on both sides of the fiber fabric. Thereby, the desired moisture-permeable waterproof fabric can be obtained.
  • the moisture-permeable waterproof fabric of the present invention obtained above has moisture permeability and waterproofness (water resistance).
  • the polyurethane resin composition for moisture-permeable waterproof fabrics of the present invention has the following effects.
  • DADCHM 4, 4'-diaminodicyclohexylmethane
  • IP A Isopropyl alcohol
  • IPDA Isophorone diamine
  • IPDI Isophorone diisocyanate
  • MPG Propylene glycol monomethyl ether
  • PEPG Polyoxyethyleneoxypropylene block copolymer diol
  • the moisture permeability was evaluated by measuring the moisture permeability according to the potassium acetate method in JIS L 1099 (Method for testing moisture permeability of textile products).
  • the waterproof property was evaluated by measuring the water resistance according to JIS L 1092 (high water pressure method for testing waterproofness of textile products). Waterproof is synonymous with water resistance.
  • washing process was performed. Washing conditions ⁇ IS IS L 0217 Washed 10 times in accordance with 103 law.
  • the heat resistance is the heat resistance required when used in wear applications. In other words, it is required to withstand heat when bonding a hot-melt seam tape.
  • a moisture-permeable waterproof fabric is stitched together to create a seam, and hot melt seam tape used to prevent seam leakage is applied at a speed of 4 m / min while applying hot air at 650 ° C. [Laminating device: QHP805, manufactured by Queen Light Co., Ltd.].
  • Those with good heat resistance do not have holes in the resin film, but those with poor heat resistance will deteriorate the resin film, open holes, and reduce water resistance.
  • a four-necked flask equipped with a stirrer and a thermometer is charged with 55 parts of PEG of Mnl, 000 (calculated from the hydroxyl value), 45 parts of PTMG of Mnl, 000 and 55.5 parts of IPDI, and 110 ° C under a dry nitrogen atmosphere. After 5 hours of reaction, the mixture was cooled to 50 ° C., and 467 parts of IPA was added and dissolved uniformly to obtain a prepolymer solution.
  • 4 parts of DADCHM, 0.5 part of diethanolamine (reaction terminator) 0.53 parts of IPA in 90 parts of IPA was added dropwise to the above prepolymer solution and reacted at 40 ° C for 1 hour to give a resin concentration of 25%.
  • hydrophilic polyurethane resin (A-1) having a viscosity of 6,000 mPa's / 20 ° C was obtained.
  • This hydrophilic polyurethane resin (A-1) has an OE group content of 30% and a hydroxyl value of 3.0.
  • diisocyanate (D) / polymer diol (C) [equivalent ratio] 2.5
  • (D) represents IPDI
  • (C) represents PEG and PTMG
  • E) represents DADCHM.
  • hydrophilic polyurethane resin (A-2) An alcohol solution of hydrophilic polyurethane resin (A-2) with a viscosity of 7,000 mPa'sZ20 ° C was obtained.
  • This hydrophilic polyurethane resin (A-2) has an OE group content of 44% and a hydroxyl value of 4.1.
  • diisocyanate (D) / polymer diol (C) [equivalent ratio] 3.5
  • diisocyanate (D) / [polymer diol (C) + chain extender (E)] [equivalent ratio] 1.05 It is.
  • (D) represents IPDI
  • (C) represents PEPG
  • (E) represents IPDA.
  • This hydrophilic polyurethane resin (A-3) has an OE group content of 60% and a hydroxyl value of 4.1.
  • Diisocyanate (HD) / polymer diol (C) [equivalent ratio] 3 ⁇ 5
  • diisocyanate (D) / [polymeric diol (C) + chain extender (E)] [equivalent ratio] 1 ⁇ 05.
  • (D) represents IPDI, (C) ⁇ or PEG, and ( ⁇ ) ⁇ or DADCHM.
  • hydrophilic polyurethane resin (X-1) having a resin concentration of 25% and a viscosity of 10,000 mPa's / 20 ° C was obtained.
  • the hydrophilic polyurethane resin (_1) has a O group content of 33% and a hydroxyl value of 0.
  • diisocyanate (D) / high molecular diol (C) [equivalent ratio] 5.0
  • diisocyanate (D) Z [polymer diol (C) + chain extender (E)] [equivalent ratio] 1.02 It is.
  • (D) represents MDI
  • (C) represents PTMG
  • (E) represents BD.
  • hydrophilic polyurethane resin (X-2) with a viscosity of 6,000mPa's / 20 ° C Obtained.
  • This hydrophilic polyurethane resin (X_ 2) has a ⁇ E group content of 5% and a hydroxyl value of 4.8.
  • diisocyanate (D) / polymer diol (C) [equivalent ratio] 2.5
  • (D) represents IPDI
  • (C) represents PEG and PTMG
  • E) represents DADCHM.
  • (D) represents IPDI
  • (C) represents PEG
  • (E) represents IPDA.
  • Polyester taffeta for both warp and horizontal yarns 83 decitex / 72 filaments, warp density 160, Z2. 54cm, horizontal density 70 / 2.54cm, polyester taffeta thickness 0.1mm
  • a fluorine-based water repellent [a water repellent used before imparting a non-porous layer of polyurethane resin to a fiber fabric.
  • Product name "Asahi Guard AG710", manufactured by Asahi Glass Co., Ltd. same as below. ] was used as the fiber fabric.
  • the following coating solution was prepared, and the coating solution was applied onto the entire surface of the release paper using a knife coater.
  • the coating solution on the release paper was dried at 100 ° C using an air oven to obtain a 30 x m nonporous layer.
  • the polyisocyanate (B) a modified urethane product of HDI [trade name “WB40_100”, manufactured by Asahi Kasei Kogyo Co., Ltd.] was used.
  • Polyisocyanate (B) [HDI urethane modified product, the same shall apply hereinafter] 4 parts IPA 40 parts
  • a moisture-permeable waterproof fabric was obtained in the same manner as in Example 1 except that an alcohol solution of the hydrophilic polyurethane resin (A-2) was used as the coating solution.
  • the performance of the obtained moisture permeable waterproof fabric is shown in Table 1.
  • a moisture-permeable waterproof fabric was obtained in the same manner as in Example 1 except that an alcohol solution of hydrophilic polyurethane resin (A-3) was used as the coating solution.
  • the performance of the obtained moisture permeable waterproof fabric is shown in Table 1.
  • a moisture-permeable waterproof fabric was obtained in the same manner as in Example 1 except that 100 parts of a DMF / MEK solution of hydrophilic polyurethane resin (X_1), 10 parts of DMF, and 30 parts of MEK were used as the coating liquid.
  • the performance of the obtained moisture permeable waterproof fabric is shown in Table 1.
  • a moisture-permeable waterproof fabric was obtained in the same manner as in Example 1 except that an alcohol solution of hydrophilic polyurethane resin (X-2) was used as the coating solution.
  • the performance of the obtained moisture permeable waterproof fabric is shown in Table 1.
  • a moisture-permeable waterproof fabric was obtained in the same manner as in Example 1 except that an alcohol solution of hydrophilic polyurethane resin (X-3) was used as the coating solution.
  • the performance of the resulting moisture-permeable waterproof fabric is shown in Table 1. It was.
  • Example 1 using only an alcohol solvent have good water resistance and moisture permeability, and in particular, Example 2 using the resin (A-2) has an excellent balance. It has become.
  • Comparative Example 1 using resin (X-1) are also good, but because DMF and MEK are used, there are risks and costs in terms of work environment sanitation and exhaust treatment. It contains a problem.
  • Example 2 Using a knife coater, directly apply the coating liquid in Example 1 to one side of the water-repellent fiber fabric in Example 1, and dry it at 100 ° C. using an air oven. A non-porous layer having a thickness of 30 xm was formed on the surface. Thereafter, aging was performed in the same manner as in Example 1 to obtain a moisture-permeable waterproof fabric having a non-porous layer of polyurethane resin formed on one side of the fiber fabric without an adhesive layer. The performance of the obtained moisture-permeable waterproof fabric is shown in Table 2.
  • Example 2 In the same manner as in Example 1, the fiber fabric and the adhesive layer on the nonporous layer were overlapped and bonded using a nip roll, and then aged at 70 ° C for 72 hours, and then the release paper was peeled off. Next, on the nonporous layer from which the release paper was peeled off, the adhesive was applied again in the form of dots, and an adhesive layer was formed using a gravure coater. Next, another water-repellent fiber fabric produced by the same method as in Example 1 was overlaid on the adhesive layer on the nonporous layer, and bonded using a nip roll.
  • Example 2 Thereafter, aging and water-repellent treatment were performed in the same manner as in Example 1, and (first fiber fabric)-(first adhesive layer)-(nonporous layer of polyurethane resin)-(second adhesive layer) ) A moisture-permeable waterproof fabric having a structure laminated in the order of (second fiber fabric) was obtained. The performance of the obtained moisture-permeable waterproof fabric is shown in Table 2.
  • Example 1 Apply the coating solution in Example 1 directly to the water-repellent fiber fabric in Example 1 with a knife coater, and dry at 100 ° C using an air oven, so that the coating solution is completely dry.
  • another fiber fabric was stacked on top of each other, and drying at 100 ° C. was continued.
  • aging and water repellent treatment were performed in the same manner as in Example 1, and a moisture-permeable layer having a nonporous layer of polyurethane resin between the first fiber fabric and the second fiber fabric without an adhesive layer interposed therebetween.
  • a waterproof fabric was obtained.
  • the performance of the obtained moisture-permeable waterproof fabric is shown in Table 2.
  • Example 2 In the same manner as in Example 1, a non-porous layer having a thickness of 15 xm was obtained on two release papers. Next, in the same manner as in Example 1, an adhesive layer is formed on each nonporous layer, and the water-repellent fiber fabric in Example 1 is sandwiched between the two adhesive layers. A nip roll was used and bonded together. Thereafter, in the same manner as in Example 1, after aging, the two release papers were peeled off to (non-porous layer of the first polyurethane resin) (first adhesive layer) (fiber cloth) Fabric)-(second adhesive layer)-(second polyurethane resin non-porous layer) in order to obtain a moisture-permeable waterproof fabric having a laminated structure. The performance of the obtained moisture-permeable waterproof fabric is shown in Table 2.
  • Example 2 In the same manner as in Example 4, a non-porous layer having a thickness of 15 zm was formed on one side of a water-repellent fiber fabric, and then aged at 70 ° C. for 72 hours. Further, a non-porous layer having a thickness of 15 zm is similarly formed on the other surface of the fiber fabric, and then aging is performed in the same manner as in Example 1 to form an adhesive layer on both surfaces of the fiber fabric. A moisture-permeable waterproof fabric having a nonporous layer of polyurethane resin was obtained without intervention. The performance of the obtained moisture-permeable waterproof fabric is shown in Table 2.
  • a moisture-permeable waterproof fabric obtained from the polyurethane resin composition of the present invention is a moisture-permeable waterproof fabric obtained from the polyurethane resin composition of the present invention.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

La présente invention concerne un tissu étanche perméable à l’humidité qui est réduit en termes de charge en ce qui concerne l'hygiène de l'environnement de travail et de traitement des gaz de décharge et est égal en ce qui concerne le revêtement d'un film (propriétés filmogènes) par comparaison aux tissus revêtus de résines classiques de polyuréthane pour des tissus étanches perméables à l’humidité utilisant un solvant tel que le DMF ou la MEC. Il est excellent en termes de résistance à l'eau (propriété d’étanchéité), de perméabilité à l’humidité et de résistance thermique. La présente invention concerne également une composition de résine de polyuréthane pour tissus étanches perméables à l’humidité qui comprend : une solution d'alcool d'une résine de polyuréthane hydrophile (A) ayant une teneur en groupe oxyéthylène de 10 à 80 % en poids ; et un polyisocyanate (B).
PCT/JP2007/050184 2006-01-10 2007-01-10 Composition de resine de polyurethane pour tissu etanche permeable a l’humidite et tissu etanche permeable a l’humidite Ceased WO2007080900A1 (fr)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110004731A (zh) * 2018-10-09 2019-07-12 东莞市科迪实业有限公司 一种防水透气纤维革的制备方法
CN113924327A (zh) * 2019-06-25 2022-01-11 Dic株式会社 湿气固化型聚氨酯树脂组合物、粘接剂、以及层叠体
CN114829700A (zh) * 2019-12-26 2022-07-29 东丽高帝斯株式会社 透湿防水布帛

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JPH0673669A (ja) * 1992-08-25 1994-03-15 Seikoh Chem Co Ltd 透湿性防水布帛の製造方法
WO1999020465A1 (fr) * 1997-10-23 1999-04-29 Komatsu Seiren Co., Ltd. Tissu impermeable a l'eau mais permeable a l'humidite, et pellicule de resine permeable a l'humidite renforcee avec du papier anti-adhesif pour la production de tissu
JP2003311862A (ja) * 2002-04-23 2003-11-06 Toray Ind Inc 透湿防水加工布帛およびそれを用いてなる衣料
JP2005154947A (ja) * 2003-11-26 2005-06-16 Toray Ind Inc 水系透湿防水複合材
JP2005239841A (ja) * 2004-02-25 2005-09-08 Sanyo Chem Ind Ltd 水系ポリウレタン樹脂エマルション

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Publication number Priority date Publication date Assignee Title
JPH0673669A (ja) * 1992-08-25 1994-03-15 Seikoh Chem Co Ltd 透湿性防水布帛の製造方法
WO1999020465A1 (fr) * 1997-10-23 1999-04-29 Komatsu Seiren Co., Ltd. Tissu impermeable a l'eau mais permeable a l'humidite, et pellicule de resine permeable a l'humidite renforcee avec du papier anti-adhesif pour la production de tissu
JP2003311862A (ja) * 2002-04-23 2003-11-06 Toray Ind Inc 透湿防水加工布帛およびそれを用いてなる衣料
JP2005154947A (ja) * 2003-11-26 2005-06-16 Toray Ind Inc 水系透湿防水複合材
JP2005239841A (ja) * 2004-02-25 2005-09-08 Sanyo Chem Ind Ltd 水系ポリウレタン樹脂エマルション

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110004731A (zh) * 2018-10-09 2019-07-12 东莞市科迪实业有限公司 一种防水透气纤维革的制备方法
CN113924327A (zh) * 2019-06-25 2022-01-11 Dic株式会社 湿气固化型聚氨酯树脂组合物、粘接剂、以及层叠体
CN113924327B (zh) * 2019-06-25 2023-10-10 Dic株式会社 湿气固化型聚氨酯树脂组合物、粘接剂、以及层叠体
CN114829700A (zh) * 2019-12-26 2022-07-29 东丽高帝斯株式会社 透湿防水布帛

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