WO2000059979A1 - Dispersions de polyurethanne bloque au dimethylpyrazol et polyisocyanate pour produits d'ensimage pour fibres de verre textile - Google Patents

Dispersions de polyurethanne bloque au dimethylpyrazol et polyisocyanate pour produits d'ensimage pour fibres de verre textile Download PDF

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Publication number
WO2000059979A1
WO2000059979A1 PCT/EP2000/002483 EP0002483W WO0059979A1 WO 2000059979 A1 WO2000059979 A1 WO 2000059979A1 EP 0002483 W EP0002483 W EP 0002483W WO 0059979 A1 WO0059979 A1 WO 0059979A1
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weight
component
optionally
dispersion
groups
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PCT/EP2000/002483
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German (de)
English (en)
Inventor
Harald Blum
Karin Naujoks
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Bayer Aktiengesellschaft
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Priority to AU38140/00A priority Critical patent/AU3814000A/en
Publication of WO2000059979A1 publication Critical patent/WO2000059979A1/fr

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    • 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
    • C—CHEMISTRY; METALLURGY
    • C03—GLASS; MINERAL OR SLAG WOOL
    • C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
    • C03C25/00—Surface treatment of fibres or filaments made from glass, minerals or slags
    • C03C25/10—Coating
    • C03C25/24—Coatings containing organic materials
    • C03C25/26—Macromolecular compounds or prepolymers
    • C—CHEMISTRY; METALLURGY
    • C03—GLASS; MINERAL OR SLAG WOOL
    • C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
    • C03C25/00—Surface treatment of fibres or filaments made from glass, minerals or slags
    • C03C25/10—Coating
    • C03C25/24—Coatings containing organic materials
    • C03C25/26—Macromolecular compounds or prepolymers
    • C03C25/32—Macromolecular compounds or prepolymers obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
    • C03C25/326—Polyureas; Polyurethanes
    • 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
    • C08G18/0804—Manufacture of polymers containing ionic or ionogenic groups
    • C08G18/0819—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups
    • C08G18/0823—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups containing carboxylate salt groups or groups forming them
    • 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
    • C08G18/0804—Manufacture of polymers containing ionic or ionogenic groups
    • C08G18/0819—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups
    • C08G18/0828—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups containing sulfonate groups or groups forming them
    • 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
    • C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
    • C08G18/4018—Mixtures of compounds of group C08G18/42 with compounds of group C08G18/48
    • 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
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/721—Two or more polyisocyanates not provided for in one single group C08G18/73 - C08G18/80
    • C08G18/722—Combination of two or more aliphatic and/or cycloaliphatic polyisocyanates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3442—Heterocyclic compounds having nitrogen in the ring having two nitrogen atoms in the ring
    • C08K5/3445—Five-membered rings

Definitions

  • the invention relates to polyurethanes containing dimethylpyrazole, polyurethane polyureas or polyureas, processes for producing such products and their use in sizes.
  • polyurethane dispersions for the production of glass fiber sizes is e.g. known from US-A 4 255 317. Also e.g. from EP-A
  • the invention relates to polyurethanes, polyurethane-polyureas or polyureas in the form of dispersions which are modified with 0.1 to 15, preferably 0.25 to 7.5% by weight of dimethylpyrazole, a process for the preparation of such
  • the invention relates to dispersions based on polyurethanes, polyurethane-polyureas or polyureas which are preferably reaction products of
  • % of a (potentially) ionic structural component consisting of at least one compound with at least one group reactive towards NCO groups and at least one, optionally at least partially neutralized, group capable of salt formation
  • the invention also relates to dispersions based on polyurethanes, polyurethane-polyureas or polyureas which are particularly preferably the reaction products of
  • a nonionic-hydrophilic structural component consisting of at least one compound which is mono- to tetrafunctional in the sense of the isocyanate addition reaction and has at least one hydrophilic polyether chain, e) 0 to 10% by weight of at least one structural component different from a) to d) component with groups of molecular weight 32 to 2500 which are reactive towards isocyanate groups and f) 0.25 to 7.5% by weight of at least one monofunctional blocking agent which consists of at least 50% dimethylpyrazole
  • Amount used that a stable dispersion is formed is formed.
  • Polyol components a) suitable for producing the dispersions according to the invention are e.g. Polyester polyols (e.g. Ulimann's Encyclopedia of Industrial Chemistry, 4th edition, volume 19, pp. 62-65). Suitable raw materials for the production of these polyester polyols are difunctional alcohols such as ethylene glycol, 1,2- and 1,3-propylene glycol, 1,3-, 1,4-, 2,3-butanediol, 1,6-hexanediol, neopentylglycol, trimethylhexane - Diol, triethylene glycol, hydrogenated bisphenols, trimethylpentanediol, diethylene diglycol, dipropylenediglycol, 1,4-cyclohexanediol, 1,4-cyclohexanedimethanol and difunctional carboxylic acids or their anhydrides such as adipic acid, phthalic acid (anhydride), isophthalic acid, maleic acid (anhydride
  • polyester polymers are monocarboxylic acids such as benzoic acid, 2-ethylhexanoic acid, oleic acid, soybean oil fatty acid, stearic, peanut oil fatty acid, linseed oil fatty acid, nonanoic acid, cyclohexane-monocarboxylic acid, isononanoic acid, sorbic acid, conjuene fatty acid, department
  • Catalementary acid such as benzoic acid, 2-ethylhexanoic acid, oleic acid, soybean oil fatty acid, stearic, peanut oil fatty acid, linseed oil fatty acid, nonanoic acid, cyclohexane-monocarboxylic acid, isononanoic acid, sorbic acid, conjuene fatty acid, department.
  • lactylic acids such as benzoic acid, 2-ethylhexanoic acid, oleic acid, soybean oil fatty acid, stearic, peanut
  • polystyrene resin Suitable polyol components a) are polycarbonate diols which can be obtained, for example, by reacting diphenyl or dimethyl carbonate with low molecular weight diols or triols or ⁇ -caprolactone-modified diols or triols.
  • polyether polyols are especially by polymerization of ethylene oxide, propylene oxide, tetrahydrofuran,
  • polyol components a) mentioned can also be used as mixtures, if appropriate also together with other polyols a) such as Polyesteramides, polyether esters, polyacrylates are used.
  • Component b) consists of at least one organic di-, tri- or poly-isocyanate with a molecular weight of 140 to 1500, preferably 168 to 262.
  • hexamethylene diisocyanate (HDI) isophorone diisocyanate (IPDI), 4,4'-diisocyanatodicyclohexylmethane are suitable (H12MDI), 1,4-butane diisocyanate, hexahydrodiisocyanatotoluene, 1, 3-bishydroxymethylcyclohexane, hexahydrodiisocyanatoxylol, nonanetriisocyanate.
  • Aromatic isocyanates such as 2,4- or 2,6-diisocyanatotoluene (TDI), xylylene diisocyanate and 4,4'-diisocyanatodiphenyl methane are also suitable, but less preferred.
  • TDI 2,4- or 2,6-diisocyanatotoluene
  • xylylene diisocyanate and 4,4'-diisocyanatodiphenyl methane are also suitable, but less preferred.
  • Known polyisocyanates based on the above and also other isocyanates with uretdione, biuret, allophanate, isocyanurate, iminoxadiazinedione or urethane structural units can also be used.
  • the use of isophorone diisocyanate, hexamethylene diisocyanate and / or 4,4'-diisocyanatodicyclohexylmethane is particularly preferred.
  • Component c) consists of at least one (potentially) ionic compound with at least one group which is reactive towards isocyanate groups. These compounds are preferably at least one, preferably one or two hydroxyl and / or primary or secondary amino groups having carboxylic acid, sulfonic acid and phosphoric acid or salts thereof. Suitable acids are e.g. Hydroxypivalic acid, dimethylolacetic acid, 2,2'-dimethylolpropionic acid, 2,2'-dimethylolbutyric acid, 2,2'-dimethylolpentanoic acid, aminobenzoic acid, addition products of acrylic acid and diamines such as e.g. Ethylenediamine or isophoronediamine.
  • Suitable acids are e.g. Hydroxypivalic acid, dimethylolacetic acid, 2,2'-dimethylolpropionic acid, 2,2'-dimethylolbutyric acid, 2,2'-dimethylolpentanoic
  • sulfonate diols of the type described in US Pat. No. 4,108,814, optionally containing ether groups, is also suitable.
  • Amino-functional sulfonates are also suitable.
  • the free acid or amino groups in particular carboxyl and sulfonic acid groups, represent the “potentially ionic or anionic” groups mentioned above.
  • salt-like groups obtained by neutralization with bases or acids are the “ionic or anionic” groups mentioned above.
  • at least 50% of the addition product of acrylic acid and isophoronediamine is used as component c).
  • the cycloaliphatic group of this hydrophilizing agent results in particularly favorable compatibility, a reduced tendency to crystallize the polymer, improved physical drying after application and overall improved
  • Component d) consists of at least one nonipnic hydrophilic compound which has one or two groups which are reactive toward isocyanate groups per molecule, in particular hydroxyl and / or primary or secondary amino groups.
  • the polyether chains of these compounds consist of at least 30% built-in ethylene oxide units, in a preferred embodiment 40 to 95% built-in ethylene oxide units in addition to 5 to 60% built-in propylene oxide units.
  • Suitable such components d) have molecular weights of 300 to 6000 and are e.g. monofunctional polyethylene
  • propylene glycol monoalkyl ethers such as Breox® 350, 550, 750 from BP Chemicals, polyether LB 25, LB 30, LB 34, LB 40 from Bayer AG, polyethylene propylene glycols such as Carbowax® 300, 400, 1000, 2000, 6000 from Union Carbide, di - or monofunctional polyetheramines such as Jeffamine® ED600, ED900, ED4000, M715, Ml 000, M2070 from Texaco.
  • Monofunctional components d) with a molecular weight of 1000 to 2500 with a built-in propylene oxide content of 15 to 57% and a built-in ethylene oxide content of 85 to 43% are particularly preferably used.
  • Components e) are preferably 62 to 400.
  • the molecular weight build-up can be influenced by chain extension, chain branching and / or chain termination and / or functional groups can be introduced. If components e) are used to produce the prepolymer, preference is given to using hydroxy-functional components e) of the type mentioned. If components e) are used for chain extension of the prepolymer in organic solution or in aqueous dispersion, di- and / or trifunctional amine components e) are preferably used. For chain termination reactions, monoamino-functional alkoxysilanes such as e.g.
  • Suitable components f) in addition to dimethylpyrazole are e.g. Diisopropylamine, triazole, dimethyl malonate, diethyl malonate, dibutyl malonate, methyl acetoacetate, ethyl acetoacetate, butyl acetoacetate, butanone oxime, cyclohexanone oxime, acetone oxime, epsilon-caprolactam, phenol, e.g. Diisopropylamine, diethylamine,
  • the reaction of the components can be carried out with the addition of catalysts such as e.g. Dibutyltin dilaurate, tin 2-octoate, dibutyltin oxide or diazabicyclononane can be carried out.
  • catalysts such as e.g. Dibutyltin dilaurate, tin 2-octoate, dibutyltin oxide or diazabicyclononane can be carried out.
  • Amines such as triethylamine, N-methylmorpholine, diisopropylamine and potassium or sodium hydroxide can be used.
  • the degrees of neutralization are between 40 and 120%.
  • the solvents which may be used to prepare the dispersion can be partially or preferably completely removed from the dispersion by distillation.
  • the dispersions preferably contain no volatile organic compounds
  • the preferred solvent is acetone.
  • Hardeners based on polyisocyanates blocked with dimethylpyrazole are also suitable for use in sizes. These hardeners contain polyisocyanates with at least one aliphatic, aromatic, heterocyclic and / or aromatic group and optionally one or more hydrophilizing groups such as mono- or dihydroxy-functional polyethers based on ethylene oxide and / or
  • Ethylene propylene oxide or polyhydroxycarboxylic acids are described, for example, in WO 97/12924 or in EP-A 159 117.
  • Preferred hardeners contain polyisocyanates with uretdione, biuret, isocyanurate, iminooxadiazinedione, allophanate and / or urethane structural units based on 1,6-hexamethylene diisocyanate, isophorone diisocyanate and / or H ⁇ -MDI.
  • the corresponding polyisocyanates are available, for example, as Desmodur N 3400®, N 3300® or N 100® from Bayer AG.
  • Proportions are mixed.
  • the sizes preferably contain 10 to 50% by weight of hardener, based on the film-forming polymer.
  • NCO-functional polyurethane prepolymer is then diluted with 550 g of acetone and reacted with 39.9 g of dimethylpyrazole until the theoretical NCO value is reached.
  • the customary auxiliaries including a lubricant and 3-aminopropyltriethoxysilane as an adhesion promoter (10% based on the amount of dispersion used), glass fibers were produced, sized, cut and dried in a customary and known manner. The glass fibers were compounded in polyamide 6 for reinforcement.
  • improved processability was achieved, which can be seen in showed a significantly reduced amount of "specks” or specks and precipitates during the sizing process and in a reduced bulk volume (1 / Kg) of the coated and crushed glass fibers.
  • the tensile and flexural strength of the test specimens produced therefrom was also 10 to 20% improved.
  • 1000 g of a difunctional polypropylene glycol with a molecular weight of 1000, 162 g of polyether LB 25, 107.2 g of trimethylolpropane and 69.4 g of a dihydroxy-functional hydrophilizing agent with sodium sulphonate groups are (6) in a 6-1 stirred vessel with stirring, cooling and heating device.
  • Molecular weight 432 weighed, homogenized at 80 ° C, cooled to 60 ° C and reacted with 932.4 g of isophorone diisocyanate until the theoretical NCO value is reached. After cooling to 45 ° C., 65.3 g of dimethylpyrazole are added so that the reaction temperature does not exceed 65 ° C.
  • a stirred vessel with a stirring, cooling and heating device, 264 g of a difunctional polyester of phthalic anhydride and hexanediol with a molecular weight of 2000, 67 g of polyether LB 25 and 6.9 g of 1,4-butanediol are homogenized at 80 ° C. and with a mixture of 85 g of isophorone diisocyanate and 24.8 g of Desmodur W (Bayer AG) until the theoretical NCO value is reached.
  • 264 g of a difunctional polyester of phthalic anhydride and hexanediol with a molecular weight of 2000 67 g of polyether LB 25 and 6.9 g of 1,4-butanediol are homogenized at 80 ° C. and with a mixture of 85 g of isophorone diisocyanate and 24.8 g of Desmodur W (Bayer AG) until the theoretical NCO value is reached.
  • a) 160 g of a difunctional polyester of adipic acid, hexanediol and neopentyl glycol with a molecular weight of 1700 and 5.8 g of polyether LB 25 are homogenized at 80 ° C. in a 1 l stirred vessel with a stirring, cooling and heating device and mixed with a mixture of 24 g of isophorone diisocyanate and 18 g of hexamethylene diisocyanate until the theoretical NCO value is reached.
  • the mixture is then diluted with 270 g of acetone and a mixture of 2.5 g of the diaminofunctional hydrophilizing agent described in Example 4), 15 g of isophoronediamine and 25 g of water are added in 5 minutes.
  • the reaction mixture is stirred at 50 ° C. for 15 minutes and then dispersed by adding 300 g of water.
  • Acetone gives a 41.5% dispersion.
  • 177 g of a polyisocyanate based on hexamethylene diisocyanate (Desmodur® N3300, Bayer AG) and 4 g of polyether LB 25, 5.2 g of 1, 4-butanediol, are placed in a 1-l stirred vessel with a stirring, cooling and heating device.
  • 30.5 g of the hydrophilizing agent described in Example 2), 55.1 g of dimethylpyrazole and 11.7 g of butanone oxime are reacted in the presence of 50 g of acetone until no more NCO groups can be detected.
  • the reaction mixture was dispersed by adding water. After the acetone has been distilled off, a 30% dispersion of a hydrophilic polyisocyanate blocked with dimethylpyrazole is obtained.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Materials Engineering (AREA)
  • Geochemistry & Mineralogy (AREA)
  • General Chemical & Material Sciences (AREA)
  • General Life Sciences & Earth Sciences (AREA)
  • Manufacturing & Machinery (AREA)
  • Wood Science & Technology (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

L'invention concerne des polyuréthannes, des polyuréthanne-polyurées ou des polyurées contenant du diméthylpyrazol, des procédés de fabrication de tels produits et leur utilisation dans des produits d'ensimage.
PCT/EP2000/002483 1999-04-01 2000-03-21 Dispersions de polyurethanne bloque au dimethylpyrazol et polyisocyanate pour produits d'ensimage pour fibres de verre textile WO2000059979A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU38140/00A AU3814000A (en) 1999-04-01 2000-03-21 Dimethyl-pyrazole blocked polyurethane dispersions and polyisocyanate for dressing glass fibres

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19914885.6 1999-04-01
DE19914885A DE19914885A1 (de) 1999-04-01 1999-04-01 Dimethylpyrazol blockierte Polyurethan-Dispersionen und Polyisocyanate für Glasfaserschlichten

Publications (1)

Publication Number Publication Date
WO2000059979A1 true WO2000059979A1 (fr) 2000-10-12

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AU (1) AU3814000A (fr)
DE (1) DE19914885A1 (fr)
WO (1) WO2000059979A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006111287A1 (fr) * 2005-04-22 2006-10-26 Bayer Materialscience Ag Composition d'enduit
WO2013174830A1 (fr) * 2012-05-24 2013-11-28 Bayer Materialscience Ag Dispersion de polyuréthane-urée aqueuse bloquée
CN106432675A (zh) * 2015-03-06 2017-02-22 科思创德国股份有限公司 含有游离酸基团的水性聚氨酯脲分散体

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10133789A1 (de) * 2001-07-16 2003-02-06 Basf Ag Wässrige Dispersionen für hydrolysefeste Beschichtungen
US6894138B1 (en) * 2003-11-26 2005-05-17 Bayer Materialscience Llc Blocked polyisocyanate
DE102006025313A1 (de) 2006-05-31 2007-12-06 Bayer Materialscience Ag Lösemittelarme oder lösemittelfreie Vernetzer-Dispersion mit Pyrazol-blockierten Isocyanatgruppen
EP2103316A1 (fr) 2008-03-20 2009-09-23 Bayer MaterialScience AG Dispersions de polyuréthane hydrophiles
DE102008025613A1 (de) 2008-05-28 2009-12-03 Bayer Materialscience Ag Hydrophile Polyurethanbeschichtungen
CA2735744A1 (fr) 2008-09-04 2010-03-11 Bayer Materialscience Ag Solutions de polyurethane hydrophiles a base de tcd
EP2298825A1 (fr) 2009-09-17 2011-03-23 Bayer MaterialScience AG Dispersions d'urées de polyuréthane hydrophiles
CN102482393B (zh) * 2009-09-17 2013-12-11 拜尔材料科学股份公司 基于环己烷二甲醇的亲水性聚氨酯脲
KR20180094919A (ko) * 2015-12-22 2018-08-24 코베스트로 도이칠란트 아게 텍스타일을 위한 저-용매 코팅 시스템
DE102019101729B4 (de) 2019-01-24 2022-07-07 Jiuhua New Materials Technology Co., Ltd. Verfahren zur Herstellung eines Polyurea-Formkörpers oder eines Polyurea-Formkörperteiles und entsprechendes Polyureaformteil
EP3875512A1 (fr) 2020-03-05 2021-09-08 Covestro Deutschland AG Dispersion de réticulant hydrophilisée non ionique ayant des groupes uréthane/urée liés thermolatants
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WO2006111287A1 (fr) * 2005-04-22 2006-10-26 Bayer Materialscience Ag Composition d'enduit
WO2013174830A1 (fr) * 2012-05-24 2013-11-28 Bayer Materialscience Ag Dispersion de polyuréthane-urée aqueuse bloquée
KR20150013177A (ko) * 2012-05-24 2015-02-04 바이엘 머티리얼사이언스 아게 수성 블로킹된 폴리우레탄-우레아 분산액
CN104350078A (zh) * 2012-05-24 2015-02-11 拜耳材料科技股份有限公司 含水的封端聚氨酯-脲分散体
US20150141573A1 (en) * 2012-05-24 2015-05-21 Bayer Materialscience Ag Aqueous blocked polyurethane-urea dispersion
JP2015523428A (ja) * 2012-05-24 2015-08-13 バイエル・マテリアルサイエンス・アクチェンゲゼルシャフトＢａｙｅｒ ＭａｔｅｒｉａｌＳｃｉｅｎｃｅ ＡＧ 水性ブロック化ポリウレタン尿素分散体
US9404020B2 (en) 2012-05-24 2016-08-02 Covestro Deutschland Ag Aqueous blocked polyurethane-urea dispersion
CN104350078B (zh) * 2012-05-24 2019-01-18 科思创德国股份有限公司 含水的封端聚氨酯-脲分散体
KR102042295B1 (ko) * 2012-05-24 2019-11-07 코베스트로 도이칠란드 아게 수성 블로킹된 폴리우레탄-우레아 분산액
CN106432675A (zh) * 2015-03-06 2017-02-22 科思创德国股份有限公司 含有游离酸基团的水性聚氨酯脲分散体

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