EP3768749A1 - Wässrige uretdiongruppenhaltige zusammensetzungen und verfahren zu deren herstellung - Google Patents
Wässrige uretdiongruppenhaltige zusammensetzungen und verfahren zu deren herstellungInfo
- Publication number
- EP3768749A1 EP3768749A1 EP19711125.5A EP19711125A EP3768749A1 EP 3768749 A1 EP3768749 A1 EP 3768749A1 EP 19711125 A EP19711125 A EP 19711125A EP 3768749 A1 EP3768749 A1 EP 3768749A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- uretdione
- acid
- group
- diisocyanate
- groups
- 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.)
- Pending
Links
Classifications
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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
- C08G18/70—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
- C08G18/798—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing urethdione groups
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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
- C08G18/08—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
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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
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
- C08G18/20—Heterocyclic amines; Salts thereof
- C08G18/2009—Heterocyclic amines; Salts thereof containing one heterocyclic ring
- C08G18/2036—Heterocyclic amines; Salts thereof containing one heterocyclic ring having at least three nitrogen atoms in the ring
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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
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
- C08G18/20—Heterocyclic amines; Salts thereof
- C08G18/2045—Heterocyclic amines; Salts thereof containing condensed heterocyclic rings
- C08G18/2063—Heterocyclic amines; Salts thereof containing condensed heterocyclic rings having two nitrogen atoms in the condensed ring system
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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
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
- C08G18/20—Heterocyclic amines; Salts thereof
- C08G18/2045—Heterocyclic amines; Salts thereof containing condensed heterocyclic rings
- C08G18/2072—Heterocyclic amines; Salts thereof containing condensed heterocyclic rings having at least three nitrogen atoms in the condensed ring system
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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
- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/2815—Monohydroxy compounds
- C08G18/282—Alkanols, cycloalkanols or arylalkanols including terpenealcohols
- C08G18/2825—Alkanols, cycloalkanols or arylalkanols including terpenealcohols having at least 6 carbon atoms
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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
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3203—Polyhydroxy compounds
- C08G18/3206—Polyhydroxy compounds aliphatic
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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
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- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3225—Polyamines
- C08G18/3234—Polyamines cycloaliphatic
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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
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3225—Polyamines
- C08G18/3246—Polyamines heterocyclic, the heteroatom being oxygen or nitrogen in the form of an amino group
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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
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3225—Polyamines
- C08G18/325—Polyamines containing secondary or tertiary amino groups
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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
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3225—Polyamines
- C08G18/3253—Polyamines being in latent form
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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
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3225—Polyamines
- C08G18/3253—Polyamines being in latent form
- C08G18/3256—Reaction products of polyamines with aldehydes or ketones
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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
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4236—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups
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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
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4862—Polyethers containing at least a part of the ether groups in a side chain
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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
- C08G18/70—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
- C08G18/725—Combination of polyisocyanates of C08G18/78 with other polyisocyanates
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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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/73—Polyisocyanates or polyisothiocyanates acyclic
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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
- C08G18/70—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
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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
- C08G18/70—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
- C08G18/7806—Nitrogen containing -N-C=0 groups
- C08G18/7818—Nitrogen containing -N-C=0 groups containing ureum or ureum derivative groups
- C08G18/7831—Nitrogen containing -N-C=0 groups containing ureum or ureum derivative groups containing biuret groups
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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
- C08G18/70—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
- C08G18/7806—Nitrogen containing -N-C=0 groups
- C08G18/7818—Nitrogen containing -N-C=0 groups containing ureum or ureum derivative groups
- C08G18/7837—Nitrogen containing -N-C=0 groups containing ureum or ureum derivative groups containing allophanate groups
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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
- C08G18/70—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
- C08G18/797—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing carbodiimide and/or uretone-imine groups
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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
- C09D175/04—Polyurethanes
- C09D175/06—Polyurethanes from polyesters
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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
- C09D175/04—Polyurethanes
- C09D175/12—Polyurethanes from compounds containing nitrogen and active hydrogen, the nitrogen atom not being part of an isocyanate group
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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
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
- C09J175/06—Polyurethanes from polyesters
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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
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
- C09J175/12—Polyurethanes from compounds containing nitrogen and active hydrogen, the nitrogen atom not being part of an isocyanate group
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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
- C08G2190/00—Compositions for sealing or packing joints
Definitions
- the present invention relates to aqueous uretdione group-containing compositions comprising or consisting of
- At least one hardener containing uretdione groups based on aliphatic, cycloaliphatic, araliphatic and / or aromatic polyisocyanates, which contains no chemically bonded hydrophilizing groups;
- the quantitative ratio of components (A) and (B) is such that the molar ratio of the uretdione present NCO groups of the harder (A) to NCO-reactive groups of the polyol (B) 3: 0.5 to 0 , 5: 3 and wherein A and B are present as a physical mixture.
- the invention relates to a process for producing a polyurethane layer using the aqueous uretdione group-containing composition of the present invention, the polyurethane layer obtained therefrom, and a substrate coated or adhered to this polyurethane layer.
- aqueous coating systems are already available for many applications, they often can not achieve the high quality level of conventional, solvent-borne coatings in terms of resistance to solvents and chemicals or even elasticity and mechanical stress.
- no polyurethane-based coating agents to be processed from an aqueous phase have hitherto become known which sufficiently satisfy the high requirements in practice.
- aqueous uretdione-containing dispersion coatings can be prepared by combining a solid uretdione compound with a molten water-dispersible resin, salting the water-dispersible resin if necessary, and dispersing the resin composition in water.
- the molten water-dispersible resin may have a functionality reactive with the uretdione compound, or the coating composition may contain another water-dispersible resin having a uretdione compound-reactive functionality.
- an epoxy resin was used. It is well known that the epoxy varnishes are inferior in most properties to polyurethane varnishes.
- EP 1687354 A1 it is also necessary for the preparation of these dispersion coatings to use an additional emulsifier, which further impairs the coating properties of the dispersion coatings.
- the production method described in EP 1687354 A1 is associated with a very high thermal load for the uretdione groups, which in practice would most likely lead to a loss of the uretdione groups.
- the dispersions described in EP 1687354 Al were applied immediately after preparation. There is no information in EP 1687354 Al about the stability of these dispersions.
- water-dispersible hydrophilic uretdione-containing polyisocyanates can be found, for example, in DE 2538484 A1 and DE 10 2005 036 654 A1.
- a hydrophilizing group ie, a carboxyl group
- DE 2538484 A nor DE 10 2005 036 654 Al give information on the stability of these dispersions.
- no physical Mixtures of a specific uretdione hardener and a specific polyol are present.
- US 2015232609A1 discloses water-dispersible hydrophilic uretdione-containing polyisocyanates obtainable by reacting a uretdione group-bearing prepolymer with an emulsifier comprising an ionogenic group, the ionic group having either a pKa> 8 or a pKb> 8 in water at room temperature.
- Such uretdione-containing reaction products showed an improved storage stability of 8 weeks at room temperature, but this is still insufficient for practical applications in industry, where in many cases long transport distances must be expected.
- the present invention particularly relates to:
- Aqueous uretdione group-containing compositions comprising or consisting of
- At least one hardener containing uretdione groups based on aliphatic, cycloaliphatic, araliphatic and / or aromatic polyisocyanates, preferably based on aliphatic, cycloaliphatic, and / or araliphatic polyisocyanates, particularly preferably based on aliphatic and / or cycloaliphatic polyisocyanates, which does not chemically bound hydrophilicizing groups;
- the quantitative ratio of the components (A) and (B) is such that the molar ratio of the uretdione NCO groups of the harder (A) to NCO-reactive groups of the polyol (B) is 3.0: 0, 5 to 0.5: 3.0, preferably from 2.5: 1.0 to 1.0: 2.5; more preferably 2.0: 2.0 to 1.0 to 1.0: 2.0 and wherein (A) and (B) exist as a physical mixture.
- Aqueous uretdione group-containing composition characterized in that the at least one uretdione group-containing curing agent (A) by reacting monomeric isocyanates comprising or consisting of at least one monomeric isocyanate selected from tetramethylene diisocyanate, cyclohexane-1,3- and 1,4-diisocyanate, pentamethylene diisocyanate, hexamethylene diisocyanate (HDI), l-isocyanato 3,3,5-trimethyl-5-isocyanatomethylcyclohexane (isophorone diisocyanate IPDI), dicyclohexylmethane 2,4'- and / or 4,4'-diisocyanate, tetramethylxylylene diisocyanate (TMXDI), triisocyanatononane, tolylene diisocyanate (TDI), diphenylmethane-2, 4'- and / or 4,
- Aqueous uretdione group-containing composition according to aspect 1 or 2 characterized in that
- uretdione group-containing hardener (A) hydroxyl-containing monomers and / or polymers are used as feedstocks for the at least one uretdione group-containing hardener (A) hydroxyl-containing monomers and / or polymers.
- Aqueous uretdione group-containing composition according to one of the preceding aspects, characterized in that
- the at least one uretdione group-containing curing agent (A) has a free NCO content of less than 5 wt .-% and a content of uretdione groups from 1 to 18 wt .-% (calculated as C2N2O2, molecular weight 84 g / mol).
- Aqueous uretdione group-containing composition according to one of the preceding aspects, characterized in that
- the aqueous composition has an acid number of 1 to 100 mg KOH / g, preferably 2 to 50 mg KOH / g, more preferably 5 to 30 mg KOH / g, preferably measured according to DIN EN ISO 2114: 2002-06 with acetone and ethanol in a weight ratio 2: 1 as a solvent, and calculated on solids content.
- Aqueous uretdione group-containing composition according to one of the preceding aspects, characterized in that
- the at least one hydroxyl-containing polyol (B) by reacting hydroxy or aminocarboxylic acids comprising or consisting of at least one carboxylic acid selected from 2,2-dimethylolacetic acid, 2,2-dimethylol butyric acid, 2,2-dimethylolpentanoic acid, dihydroxysuccinic acid, a, W-diaminovaleric acid or mixtures thereof, preferably from dimethylolpropionic acid or hydroxypivalic acid.
- Aqueous uretdione group-containing composition according to one of the preceding aspects, characterized in that
- the at least one hydroxy group-containing polyol (B) has an OH content greater than 1% by weight, calculated as OH group to solids content, molecular weight 17 g / mol, and a number average molecular weight Mn of 500 to 20,000 g / mol.
- the solvent is selected from acetone, methyl ethyl ketone, ethyl acetate, butyl acetate, xylene, heavy benzene, such as the commercially available Solvesso 100 or Solvesso 150,
- Aqueous uretdione dispersion according to one of the preceding aspects, characterized in that
- auxiliaries and additives are selected from the group of flow control agents, for example polysilicones or acrylates, light stabilizers, for example sterically hindered amines, catalysts, for example tin (II) 2-ethylhexanoate or dibutyltin dilaurate, fillers and pigments, for example titanium dioxide, or Mixtures thereof.
- flow control agents for example polysilicones or acrylates
- light stabilizers for example sterically hindered amines
- catalysts for example tin (II) 2-ethylhexanoate or dibutyltin dilaurate
- fillers and pigments for example titanium dioxide, or Mixtures thereof.
- pigments for example titanium dioxide, or Mixtures thereof.
- step iii) curing the mixture from step iii) with heat from 40 ° C to 180 ° C for up to 180 minutes.
- Harder (A) containing at least one hydroxy group-containing polyol (B) was obtained in the absence of water and subsequent dispersion with water. 13.
- the average molecular weight is defined according to this invention as the number average molecular weight Mn, unless explicitly stated otherwise.
- Mn is determined by gel permeation chromatography (GPC) at 23 ° C in tetrahydrofuran as a solvent. The measurement is carried out as described in DIN 55672-1: 2016-03: "Gel Permeation Chromatography, Part 1 - Tetrahydrofuran as Eluent” (SECURITY GPC system from PSS Polymer Service, flow rate 1.0 ml.
- percentages by weight in the present invention refer to the total weight of the particular system or the total weight of the particular component.
- a copolymer may contain a given monomer in weight percent, in which case the weight percentages would be based on the total weight of the copolymer.
- At least one refers to the nature of the compounds rather than individual molecules.
- at least one polyol is to be understood as containing at least one type of polyol, but contained in an arbitrary number of molecules in the composition.
- two or more types of polyols may be present in any arbitrary number, if the amounts are not defined.
- the aqueous uretdione group-containing composition is substantially free of another co-emulsifier (in addition to component (B)).
- the term "substantially free of” according to the present invention is defined as preferably less than 1 wt%, more preferably less than 0.25 wt%, even more preferably less than 0.1 wt%. , most preferably less than 0.01 wt .-% or no fraction of the respective compound, each based on the total weight of the aqueous uretdione groups-containing composition.
- the aqueous uretdione group-containing composition of the present invention is preferably a polyurethane-based composition.
- Suitable polyisocyanates containing uretdione groups as starting compounds for component (A) are polyisocyanates containing at least one isocyanate group and at least one Uretdion group included. These are prepared, as described, for example, in WO 02/92657 A1 or WO 2004/005364 A1 by reaction of suitable starting isocyanates (al). Here, under catalysis, for example with triazolates or 4-dimethylaminopyridine (DMAP) as catalysts, some of the isocyanate groups are converted into uretdione groups.
- DMAP 4-dimethylaminopyridine
- isocyanates (a1) from which the uretdione-containing building blocks are synthesized are tetramethylene diisocyanate, cyclohexane-1,3- and 1,4-diisocyanate, pentamethylene diisocyanate, hexamethylene diisocyanate (HDI), 1-isocyanato-3,3,5 trimethyl-5-isocyanatomethylcyclohexane (isophorone diisocyanate IPDI), dicyclohexylmethane-2,4'- and / or 4,4'-diisocyanate,
- TXDI Tetramethylxylylene diisocyanate
- TDI Triisocyanatononan
- MDI diphenylmethane-2,4'- and / or 4,4'-diisocyanate
- MDI triphenylmethane-4,4'-diisocyanate or naphthylene-l, 5-diisocyanate and any Mixtures of such isocyanates.
- component (A) may also have isocyanurate, biuret, allophanate, urethane and / or urea structures.
- reaction of these uretdione group-carrying polyisocyanates to uretdione-containing hard (A) involves the reaction of the free NCO groups of the abovementioned polyisocyanates with a polyol component (bl), optionally with the concomitant use of the polyol component (b2).
- the polyol component (bl) preferably has a hydroxyl group functionality of> 2 and a molecular weight M n of 62 to 500 g / mol, preferably 62 to 400 g / mol, particularly preferably 62 to 300 g / mol.
- the polyol component (bl) preferably contains 2- to 6-valent polyol components of molecular weight Mn of 62 to 500 g / mol, preferably 62 to 400 g / mol, particularly preferably 62 to 300 g / mol.
- Preferred polyol components (bl) are, for example, 1,4- and / or 1,3-butanediol, 1,6-hexanediol, 2,2,4-trimethyl-1,3-pentanediol, trimethylolpropane, polyester and / or polyether polyols of the middle one Molar weight M n of less than or equal to 500 g / mol.
- Suitable linear difunctional polyols (b2) are selected from the group of polyethers, polyesters, polycaprolactone diols and / or polycarbonates.
- the polyol component (b2) contains at least one diol containing ester groups of molecular weight Mn from 350 to 4000 g / mol, preferably from 350 to 2000 g / mol, particularly preferably from 350 to 1000 g / mol. It is the average, calculated from the hydroxyl number molecular weight.
- the ester diols are mixtures in which, in minor amounts, individual constituents may also be present which are lower or higher having these limits lying molecular weight.
- These are the polyester diols known per se, which are built up from diols and dicarboxylic acids.
- Suitable diols are, for example, 1,4-dimethylolcyclohexane, 1,4- or 1,3-butanediol, 1,6-hexanediol, neopentyl glycol, 2,2,4-trimethyl-1,3-pentanediol, trimethylolpropane and also pentaerythritol or mixtures thereof diols.
- Suitable dicarboxylic acids are, for example, aromatic dicarboxylic acids such as phthalic acid, isophthalic acid and terephthalic acid, cycloaliphatic dicarboxylic acids such as hexahydrophthalic acid, tetrahydrophthalic acid, endomethylenetetrahydrophthalic acid or its anhydrides and aliphatic dicarboxylic acids which are preferably used, such as succinic acid, glutaric acid, adipic acid, suberic acid, azelaic acid and sebacic acid or their anhydrides.
- aromatic dicarboxylic acids such as phthalic acid, isophthalic acid and terephthalic acid
- cycloaliphatic dicarboxylic acids such as hexahydrophthalic acid, tetrahydrophthalic acid, endomethylenetetrahydrophthalic acid or its anhydrides
- aliphatic dicarboxylic acids which are preferably used, such as succinic acid,
- Polyester diols based on adipic acid, phthalic acid, isophthalic acid and tetrahydrophthalic acid are preferably used as component (b2).
- preferred diols for example, 1,4- or 1,3-butanediol, 1,6-hexanediol or trimethylolpropane and mixtures thereof are used.
- component (b2) are polycaprolactone diols of average molecular weight from 350 to 4000 g / mol, preferably from 350 to 2000 g / mol, particularly preferably from 350 to 1000 g / mol, which in a conventional manner from a diol or diol mixture the type exemplified above as starter, and lactones such as .beta.-propiolactone, g-butyrolactone, g- and d-valerolactone, e-caprolactone, 3,5,5- and 3,3,5-trimethylcaprolactone or any mixtures of such lactones have been produced.
- lactones such as .beta.-propiolactone, g-butyrolactone, g- and d-valerolactone, e-caprolactone, 3,5,5- and 3,3,5-trimethylcaprolactone or any mixtures of such lactones have been produced.
- Particularly preferred are those polycaprolactone dio
- linear polyol component (b2) it is also possible to use (co) polyethers of ethylene oxide, propylene oxide and / or tetrahydrofuran, which consist of less than 30 mol% of ethylene oxide units.
- polyethers having an average molecular weight Mn of from 500 to 2000 g / mol such as e.g. Polypropylene oxides or polytetrahydrofurandiols.
- hydroxyl-containing polycarbonates preferably average molecular weight Mn of from 400 to 4000 g / mol, preferably from 400 to 2000 g / mol, for example hexanediol polycarbonate and polyestercarbonates.
- diol component (b2) in the preparation of the curing agent (A) containing uretdione groups it is also possible to use diols having an average molecular weight, calculated from functionality and hydroxyl number, of 134 to 349 g / mol, preferably 176 to, low molecular weight ester groups 349 g / mol, are used. These are, for example, the per se known, ester-containing diols or mixtures of such diols, as they are, for. B. by reacting alcohols with minor amounts of dicarboxylic acids, corresponding dicarboxylic anhydrides, corresponding dicarboxylic acid esters of lower alcohols or lactones.
- Suitable acids are succinic acid, adipic acid, sebacic acid, phthalic acid, isophthalic acid, phthalic anhydride, tetrahydrophthalic acid, maleic acid, maleic anhydride, terephthalic acid dimethyl ester and terephthalic acid bis-glycol ester.
- Suitable lactones for preparing these ester diols are, for example, ⁇ -propiolactone, g-butyrolactone, g- and d-valerolactone, ⁇ -caprolactone, 3,5,5- and 3,3,5-trimethylcaprolactone or any desired mixtures of such lactones.
- uretdione groups having curing agent (A) and amino-functional compounds can be used.
- suitable low molecular weight amino-functional compounds are aliphatic and cy cloaliphatic amines and amino alcohols with primary and / or secondary bound amino groups, such as. B.
- cyclohexylamine 2-methyl-l, 5-pentanediamine, diethanolamine, monoethanolamine, propylamine, butylamine, dibutylamine, hexylamine, monoisopropanolamine, diisopropanolamine, ethylenediamine, 1,3-diaminopropane, 1,4-diaminobutane, isophoronediamine, diethylenetriamine, ethanolamine, Aminoethylethanolamine, diaminocyclohexane, hexamethylenediamine, methyliminobispropylamine, iminobispropylamine, bis (aminopropyl) piperazine, aminoethylpiperazine, 1,2-diaminocyclohexane, triethylenetetramine, tetraethylenepentamine, bis (4-amino-cyclohexyl) methane, bis (4-amino-3-methylcyclohexyl) methane
- solvents may be used in the preparation of the curing agent (A) containing uretdione groups.
- Suitable solvents for uretdione curing agents (A) are all liquid substances which do not react with other ingredients, eg. Acetone, methyl ethyl ketone, ethyl acetate, butyl acetate, xylene, heavy benzene, such as the commercially available Solvesso 100 and Solvesso 150, propylene glycol mono-n-butyl ether, dipropylene glycol dimethyl ether, methoxypropyl acetate, dibasic esters or mixtures thereof.
- the uretdione group-containing hardeners (A) are substantially free of ionic or non-ionic, chemically-bonded hydrophilicizing groups.
- ionic hydrophilizing groups those skilled in the art will understand groups having an ability to form anions or cations.
- Groups capable of anion or cation formation are those which can be converted by chemical reaction into an anionic or cationic group, in particular by neutralization.
- the uretdione group-containing curing agents (A) are preferably free of anionic-capable, carboxyl-containing polyols or diols, e.g. Dihydroxycarboxylic acids, such as ⁇ , ⁇ -dialkylolalkanoic acids, in particular ⁇ , ⁇ -dimethylolalkanoic acids, such as 2,2-dimethylolacetic acid, 2,2-dimethylolpropionic acid, 2,2-dimethylolbutyric acid, 2,2-dimethylolpentanoic acid,
- Dihydroxycarboxylic acids such as ⁇ , ⁇ -dialkylolalkanoic acids, in particular ⁇ , ⁇ -dimethylolalkanoic acids, such as 2,2-dimethylolacetic acid, 2,2-dimethylolpropionic acid, 2,2-dimethylolbutyric acid, 2,2-dimethylolpentanoic acid,
- the hardeners (A) containing uretdione groups are preferably free from amino-containing compounds capable of anion formation such as, for example, ⁇ , W-diaminovaleric acid or 2,4-diamino-toluene-sulphonic acid.
- the uretdione group-containing hardeners (A) are also preferably free of sulfonic acid groups capable of forming anions.
- uretdione hardening agents (A) are preferably free of cation-forming compounds from the group of tertiary amino or ammonium compounds, e.g. Tris (hydroxyalkyl) amines, N, N'-bis (hydroxyalkyl) alkylamines, N-hydroxyalkyldialkylamines, trisaminoalkylamines, N, N'-bisaminoalkylalkylamines, N-aminoalkyldialkylamines, and mixtures thereof.
- Tris (hydroxyalkyl) amines e.g. Tris (hydroxyalkyl) amines, N, N'-bis (hydroxyalkyl) alkylamines, N-hydroxyalkyldialkylamines, trisaminoalkylamines, N, N'-bisaminoalkylalkylamines, N-aminoalkyldialkylamines, and mixtures thereof.
- the uretdione group-containing curing agents (A) are furthermore preferably free from nonionically hydrophilizing compounds, such as, for example, polyalkylene oxide polyether alcohols or polyalkylene oxide polyetheramines.
- the hardeners (A) containing uretdione groups are preferably free of polyethylene oxide polyethers or mixed polyalkylene oxide polyethers whose alkylene oxide units consist of at least 30 mol% of ethylene oxide units.
- Preferred uretdione hardeners (A) have a free NCO content of less than 5% by weight and a content of uretdione groups of 1 to 18% by weight (calculated as C2N2O2, molecular weight 84 g / mol).
- the hardeners (A) may also have isocyanurate, biuret, allophanate, urethane and / or urea structures.
- the composition also contains at least one hydroxyl-containing polyol which contains at least one chemically bonded carboxylic acid group (component (B)).
- Suitable polyols (B) may be selected from polyester polyols, polyether polyols, polyurethane ether polyols, polyurethane ester polyols, polycaprolactone polyols,
- Polyetheresterpolyolen, polycarbonate polyols, C2-io-hydrocarbon having at least two hydroxyl groups or mixtures thereof are selected, as long as such polyols have at least one chemically bonded carboxylic acid groups.
- the suitable polyols (B) are preferably from the group of polyurethane ether polyols, polyurethane ester polyols,
- Polycaprolactone polyols or polycarbonate polyols Particularly preferred are polyurethane ester polyols (B) prepared from 5 to 80 wt .-%, preferably 10 to 60 wt .-% of isocyanates (al),
- At least one chemically bonded carboxylic acid group-containing starting component (b3) for the polyols (B) are suitable such polyols, preferably diols, containing at least one carboxylic acid group, generally 1 to 3 carboxylic acid groups per molecule.
- dihydroxycarboxylic acids such as ⁇ , ⁇ -dialkylolalkanoic acids, especially ⁇ , ⁇ -dimethylolalkanoic acids, such as 2,2-dimethyloleacetic acid, 2,2-dimethylolpropionic acid, 2,2-dimethylolbutyric acid, 2,2-dimethylolpentanoic acid, dihydroxysuccinic acid, furthermore polyhydroxy acids, such as Gluconic acid, or aminocarboxylic acids such as a, W-diaminovaleric acid, and 2,4-diamino-toluene-sulfonic acid. It is also possible to use mixtures of the compounds described above.
- At least one chemically bonded carboxylic acid group-containing starting component (b3) for the polyols (B) is particularly preferred 2,2-dimethylolpropionic acid.
- monohydroxy-functional compounds which have at least one carboxylic acid group, for example hydroxypivalic acid or hydroxydecanoic acid.
- Suitable polyols (B) are polyols which preferably have an OH content of more than 1% by weight (calculated as OH group on solid content, molecular weight 17 g / mol) and preferably a number average Molecular weight Mn of 500 to 20,000 g / mol, preferably from 500 to 10,000 g / mol, particularly preferably from 500 to 5000 g / mol.
- the preparation of the polyurethane resin used according to the invention is preferably carried out by reacting a non-aqueous resin precursor of the polyol (B) with at least one uretdione curing agent (A) based on aliphatic, (cyclo) aliphatic, araliphatic and / or aromatic polyisocyanates, which contains no chemically bound hydrophilizing groups, homogeneously mixed in a nonaqueous system.
- the carboxylic acid groups present in the polyol (B) are preferably neutralized to at least 50%, more preferably 80% to 120%, particularly preferably 95 to 105% with suitable neutralizing agents and then dispersed with deionized water.
- the neutralization may be carried out before, during or after the dispersing step. However, preference is given to neutralization before the addition of water.
- Suitable neutralizing agents are, for example, triethylamine, dimethylaminoethanol, dimethylcyclohexylamine, triethanolamine, methyldiethanolamine, diisopropanolamine, ethyldiisopropylamine, diisopropylcyclohexylamine, N-methylmorpholine, 2-amino-2-methyl-1-propanol, ammonia or other customary neutralizing agents or neutralization mixtures thereof. Preference is given to tert. Amines such as e.g. Triethylamine, diisopropylhexylamine, particularly preferred is dimethylethanolamine.
- the neutralizing agents are to be counted among the group of auxiliary additives (D).
- solvents under (C) all liquid substances are suitable which do not react with other ingredients.
- Preferred are acetone, methyl ethyl ketone, ethyl acetate, butyl acetate, xylene, heavy benzene, such as the commercially available Solvesso 100 and Solvesso 150, propylene glycol mono-n-butyl ether, dipropylene glycol dimethyl ether, methoxypropyl acetate, dibasic esters or mixtures thereof.
- the solvent used can then be removed by distillation.
- customary additives such as leveling agents, for.
- leveling agents for.
- polysilicones or acrylates light stabilizers, for.
- sterically hindered amines, catalysts for example, tin (II) 2-ethylhexyloctoate or dibutyltin dilaurate or other auxiliaries, as described, for.
- tin (II) 2-ethylhexyloctoate or dibutyltin dilaurate or other auxiliaries as described, for.
- fillers and pigments such as titanium dioxide may be added in an amount of up to 50% by weight of the aqueous composition.
- the aqueous uretdione group-containing compositions contains or consists of
- Polyester 1 an aliphatic polyester prepared from 1419 g of trimethylolpropane, 4773 g of neopentyl glycol, 3093 g of adipic acid, 4101 g of isophthalic acid and 267 g of 1,2-propylene glycol having an acid number ⁇ 3 mg KOH / g and an OH number of 181 mg KOH / G.
- the NCO contents were determined titrimetrically in accordance with DIN EN ISO 11909: 2007-05.
- the determination of the average particle size (MTG) was carried out with a Zetasizer Nano Fa.
- pH value determination was carried out with a pH meter according to DIN ISO 976: 2008-07 diluted 1: 4 with distilled water.
- the residual monomer contents were measured according to DIN EN ISO 10283 by gas chromatography with an internal standard.
- the pendulum hardness was measured on a standardized coil test panel (Coil Coating black - CS 200570, Heinz Zanders für-Blech-Logiding) according to DIN EN ISO 1522: 2007-04 with a König pendulum.
- Part 1 from Table 1 was weighed into a stirring apparatus under nitrogen and homogenized for 1 hour at 60 ° C. Thereafter, Part 2 was added at 55 ° C so that by the exothermic reflux has arisen. The reaction mixture was refluxed until the NCO content dropped below 0.05%. Subsequently, the reaction mixture was cooled to 50 ° C, Part 3 was added and stirred for 1 hr. At 50 ° C. Thereafter, part 4 was added and stirred for 30 min. Finally, part 5 was stirred in 15 minutes and acetone distilled off in vacuo.
- the dispersion remained stable for 14 months at 23 ° C.
- Example 2 was prepared as Example 1, except that 718 g of crosslinker 1 solution and 38 g of dimethylethanolamine were used.
- the dispersion thus obtained has the following characteristics:
- the dispersion remained stable for 14 months at 23 ° C.
- Example 3 was prepared as Example 1, except that the following quantity framework from Table 2 was used: TABLE 2
- the dispersion remained stable at 23 ° C for 10 months.
- IPDI isophorone diisocyanate
- DMAP 4-dimethylaminopyridine
- the dispersions were mixed in a speed mixer at 2000 rpm for 1 minute and applied to a coil plate with a doctor blade having a layer thickness of 180 ⁇ m (wet).
- the plates with the applied wet paints were aerated for 5 min at room temperature and then baked for 30 min at 180 ° C and stored for 4 days at room temperature.
- the stored films were evaluated by application technology (Table 4). Table 4
- the uretdione-containing dispersions according to the invention give hard and stable coatings.
Abstract
Description
Claims
Applications Claiming Priority (16)
Application Number | Priority Date | Filing Date | Title |
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US15/933,495 US11312881B2 (en) | 2018-03-23 | 2018-03-23 | One component polyurethane/allophanate formulations with reactive reducer |
EP18163621.8A EP3543270A1 (de) | 2018-03-23 | 2018-03-23 | Katalysatorsystem für uretdiondispersionen |
US15/933,470 US11292864B2 (en) | 2018-03-23 | 2018-03-23 | Compositions using polyuretdione resins |
US15/933,527 US20190292296A1 (en) | 2018-03-23 | 2018-03-23 | Polyol acid neutralization for low temperature uretdione curing |
US15/933,553 US10633477B2 (en) | 2018-03-23 | 2018-03-23 | Extended pot-life for low temperature curing polyuretdione resins |
US15/933,570 US10731051B2 (en) | 2018-03-23 | 2018-03-23 | Basecoat acid neutralization through inorganic salts |
US15/933,487 US20190292305A1 (en) | 2018-03-23 | 2018-03-23 | Uretdione based polyurethane compositions |
US15/933,507 US20190292294A1 (en) | 2018-03-23 | 2018-03-23 | One component allophanate formulations through basecoat catalyst migration |
EP18163620.0A EP3543269A1 (de) | 2018-03-23 | 2018-03-23 | Uretdionhaltige polyurethandispersionen mit hydrophilen gruppen |
US15/933,500 US10696775B2 (en) | 2018-03-23 | 2018-03-23 | Curing for polyallophanate compositions through undercoat acid neutralization |
US15/933,511 US11440988B2 (en) | 2018-03-23 | 2018-03-23 | Polyuretdione-containing resin blend compositions |
US15/933,475 US11008416B2 (en) | 2018-03-23 | 2018-03-23 | Aqueous, curable composition, comprising dispersed uretdione prepolymer, reactant and azolate |
EP18163625.9A EP3543271A1 (de) | 2018-03-23 | 2018-03-23 | Wässrige uretdiongruppenhaltige zusammensetzungen und verfahren zu deren herstellung |
EP18181876.6A EP3590987A1 (de) | 2018-07-05 | 2018-07-05 | Wässrige uretdiongruppenhaltige zusammensetzungen und verfahren zu deren herstellung |
EP18181877.4A EP3590988A1 (de) | 2018-07-05 | 2018-07-05 | Wässrige uretdiongruppenhaltige zusammensetzungen und verfahren zu deren herstellung |
PCT/EP2019/057064 WO2019180127A1 (de) | 2018-03-23 | 2019-03-21 | Wässrige uretdiongruppenhaltige zusammensetzungen und verfahren zu deren herstellung |
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EP3768749A1 true EP3768749A1 (de) | 2021-01-27 |
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EP19713663.3A Withdrawn EP3768747A1 (de) | 2018-03-23 | 2019-03-21 | Wässrige, härtbare zusammensetzung mit dispergiertem uretdion-präpolymer, reaktand und azolat |
EP19711125.5A Pending EP3768749A1 (de) | 2018-03-23 | 2019-03-21 | Wässrige uretdiongruppenhaltige zusammensetzungen und verfahren zu deren herstellung |
EP19713667.4A Withdrawn EP3768755A1 (de) | 2018-03-23 | 2019-03-21 | Zusammensetzungen mit polyuretdionharzen |
EP19713670.8A Withdrawn EP3768758A1 (de) | 2018-03-23 | 2019-03-21 | Einkomponenten-polyurethan-/allophanatformulierungen mit reaktivem reduktionsmittel |
EP19713669.0A Withdrawn EP3768757A1 (de) | 2018-03-23 | 2019-03-21 | Einkomponentige allophanatformulierungen durch grundschicht-katalysatormigration |
EP19711129.7A Pending EP3768751A1 (de) | 2018-03-23 | 2019-03-21 | Wässrige uretdiongruppenhaltige zusammensetzungen und verfahren zu deren herstellung |
EP19711127.1A Withdrawn EP3768748A1 (de) | 2018-03-23 | 2019-03-21 | Katalysatorsystem für uretdiondispersionen |
EP19711126.3A Pending EP3768750A1 (de) | 2018-03-23 | 2019-03-21 | Wässrige uretdiongruppenhaltige zusammensetzungen und verfahren zu deren herstellung |
EP19711128.9A Withdrawn EP3768745A1 (de) | 2018-03-23 | 2019-03-21 | Uretdionhaltige polyurethandispersionen mit hydrophilen gruppen |
EP19714972.7A Withdrawn EP3768759A1 (de) | 2018-03-23 | 2019-03-21 | Verlängerte topfzeit für niedrigtemperaturhärtende polyuretdionharze |
EP19713668.2A Pending EP3768756A1 (de) | 2018-03-23 | 2019-03-21 | Polyolsäureneutralisierung zur uretdionhärtung bei niedriger temperatur |
EP19713665.8A Withdrawn EP3768753A1 (de) | 2018-03-23 | 2019-03-21 | Verbesserte härtung für polyallophanatzusammensetzungen durch säureneutralisierung der grundierung |
EP19713666.6A Withdrawn EP3768754A1 (de) | 2018-03-23 | 2019-03-21 | Polyuretdionhaltige harzmischungszusammensetzungen |
EP19713339.0A Pending EP3768752A1 (de) | 2018-03-23 | 2019-03-21 | Neutralisierung der basisschicht durch anorganische salze |
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Application Number | Title | Priority Date | Filing Date |
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EP19713667.4A Withdrawn EP3768755A1 (de) | 2018-03-23 | 2019-03-21 | Zusammensetzungen mit polyuretdionharzen |
EP19713670.8A Withdrawn EP3768758A1 (de) | 2018-03-23 | 2019-03-21 | Einkomponenten-polyurethan-/allophanatformulierungen mit reaktivem reduktionsmittel |
EP19713669.0A Withdrawn EP3768757A1 (de) | 2018-03-23 | 2019-03-21 | Einkomponentige allophanatformulierungen durch grundschicht-katalysatormigration |
EP19711129.7A Pending EP3768751A1 (de) | 2018-03-23 | 2019-03-21 | Wässrige uretdiongruppenhaltige zusammensetzungen und verfahren zu deren herstellung |
EP19711127.1A Withdrawn EP3768748A1 (de) | 2018-03-23 | 2019-03-21 | Katalysatorsystem für uretdiondispersionen |
EP19711126.3A Pending EP3768750A1 (de) | 2018-03-23 | 2019-03-21 | Wässrige uretdiongruppenhaltige zusammensetzungen und verfahren zu deren herstellung |
EP19711128.9A Withdrawn EP3768745A1 (de) | 2018-03-23 | 2019-03-21 | Uretdionhaltige polyurethandispersionen mit hydrophilen gruppen |
EP19714972.7A Withdrawn EP3768759A1 (de) | 2018-03-23 | 2019-03-21 | Verlängerte topfzeit für niedrigtemperaturhärtende polyuretdionharze |
EP19713668.2A Pending EP3768756A1 (de) | 2018-03-23 | 2019-03-21 | Polyolsäureneutralisierung zur uretdionhärtung bei niedriger temperatur |
EP19713665.8A Withdrawn EP3768753A1 (de) | 2018-03-23 | 2019-03-21 | Verbesserte härtung für polyallophanatzusammensetzungen durch säureneutralisierung der grundierung |
EP19713666.6A Withdrawn EP3768754A1 (de) | 2018-03-23 | 2019-03-21 | Polyuretdionhaltige harzmischungszusammensetzungen |
EP19713339.0A Pending EP3768752A1 (de) | 2018-03-23 | 2019-03-21 | Neutralisierung der basisschicht durch anorganische salze |
Country Status (3)
Country | Link |
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EP (14) | EP3768747A1 (de) |
CN (10) | CN111886273A (de) |
WO (15) | WO2019180130A1 (de) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN110698622A (zh) * | 2019-10-12 | 2020-01-17 | 北京长润化工有限公司 | 酮亚胺潜伏固化剂和具有其的反应型聚氨酯热熔胶及应用 |
CN113816812A (zh) * | 2021-08-27 | 2021-12-21 | 湖北航天化学技术研究所 | 一种液体型脲类降速剂、制备方法及固体推进剂 |
Family Cites Families (100)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3169945A (en) | 1956-04-13 | 1965-02-16 | Union Carbide Corp | Lactone polyesters |
DE1078568B (de) | 1957-08-30 | 1960-03-31 | Basf Ag | Verfahren zur Herstellung von Carbonsaeureamidinen |
NL126422C (de) | 1960-10-14 | |||
DE2312391A1 (de) * | 1973-03-13 | 1974-09-19 | Bayer Ag | Pulverfoermige, vernetzbare ueberzugsmittel |
DE2456469C2 (de) | 1974-11-29 | 1983-01-13 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von in Wasser löslichen bzw. dispergierbaren blockierten Polyisocyanaten und ihre Verwendung als Beschichtungsmittel |
DE2538484C2 (de) * | 1975-08-29 | 1985-02-07 | Chemische Werke Hüls AG, 4370 Marl | Verfahren zur Herstellung von lösungsmittelfreien, ausschließlich wäßrigen, thermisch vernetzbaren lagerstabilen Dispersionen von lichtstabilen Polyurethanen |
US4119602A (en) | 1977-04-07 | 1978-10-10 | W. R. Grace & Co. | Aqueous urethane codispersions |
DE2853937A1 (de) | 1978-12-14 | 1980-07-03 | Bayer Ag | Verfahren zur herstellung von wasserdispergierbaren oder -loeslichen blockierten polyisocyanaten, die nach dem verfahren erhaeltlichen blockierten polyisocyanate, sowie diese blockierte polyisocyanate als isocyanatkomponente enthaltende lackbindemittel |
DE3030572A1 (de) * | 1980-08-13 | 1982-03-18 | Chemische Werke Hüls AG, 4370 Marl | Verfahren zur herstellung von uretdiongruppenhaltigen polyadditionsprodukten sowie die danach hergestellten produkte |
US4496684A (en) | 1984-06-01 | 1985-01-29 | Olin Corporation | Uretdione group-containing polyurethane oligomers and aqueous dispersions thereof |
JPS63284273A (ja) * | 1987-05-15 | 1988-11-21 | Dainippon Ink & Chem Inc | 粉体塗料用樹脂組成物 |
EP0424697B1 (de) | 1989-10-03 | 1996-04-17 | Asahi Glass Company Ltd. | Wässrige Polyurethanzusammensetzung und ihre Verwendung |
DE4001783A1 (de) | 1990-01-23 | 1991-07-25 | Bayer Ag | Polyisocyanatgemische, ein verfahren zu ihrer herstellung und ihre verwendung als bindemittel fuer ueberzugsmittel oder als reaktionspartner fuer gegenueber isocyanatgruppen oder carboxylgruppen reaktionsfaehige verbindungen |
CA2047635C (en) * | 1990-07-30 | 2003-09-30 | Terry A. Potter | Two-component aqueous polyurethane dispersions |
DE4136618A1 (de) * | 1991-11-07 | 1993-05-13 | Bayer Ag | Wasserdispergierbare polyisocyanatgemische |
DE4221924A1 (de) | 1992-07-03 | 1994-01-13 | Bayer Ag | In Wasser lösliche oder dispergierbare Polyisocyanatgemische und ihre Verwendung in Einbrennlacken |
DE4322242A1 (de) * | 1993-07-03 | 1995-01-12 | Basf Lacke & Farben | Wäßriges Zweikomponenten-Polyurethan-Beschichtungsmittel, Verfahren zu seiner Herstellung und seine Verwendung in Verfahren zur Hestellung einer Mehrschichtlackierung |
CA2134009C (en) | 1993-11-11 | 2005-03-08 | Oleg Werbitzky | Bicyclic amidines, process for their preparation, and their use as catalyst |
DE4406444A1 (de) | 1994-02-28 | 1995-08-31 | Huels Chemische Werke Ag | Hydroxyl- und uretdiongruppenhaltige Polyadditionsprodukte und Verfahren zu ihrer Herstellung sowie deren Verwendung zur Herstellung abspaltfreier Polyurethan-Pulverlacke hoher Reaktivität und die danach hergestellten Polyurethan-Pulverlacke |
US5795950A (en) * | 1994-05-20 | 1998-08-18 | Asahi Kasei Kogyo Kabushiki Kaisha | Straight chain crystalline polyuretdione |
ES2208660T3 (es) * | 1994-06-06 | 2004-06-16 | Basf Corporation | Composiciones de revestimiento que contienen aldimina e isocianato y proceso para su preparacion. |
US5523376A (en) * | 1994-12-21 | 1996-06-04 | Bayer Corporation | Coating compositions based on aldimines and polyisocyanates containing uretdione groups |
CA2245730C (en) * | 1996-02-17 | 2006-01-03 | Imperial Chemical Industries Plc | Coating composition |
DE19611849A1 (de) | 1996-03-26 | 1997-10-02 | Bayer Ag | Neue Isocyanattrimerisate und Isocyanattrimerisatmischungen, deren Herstellung und Verwendung |
DE19616496A1 (de) | 1996-04-25 | 1997-10-30 | Bayer Ag | Abspaltfreier Polyurethan-Pulverlack mit niedriger Einbrenntemperatur |
DE19628394A1 (de) * | 1996-07-13 | 1998-01-15 | Huels Chemische Werke Ag | Wärmehärtende Einkomponenten-Klebstoffe auf Basis von Polyurethanen, ein Verfahren zu ihrer Herstellung sowie deren Verwendung |
US5977285A (en) * | 1997-08-07 | 1999-11-02 | Akzo Nobel N.V. | Sprayable coating compositions comprising oxazolidines, isocyanates and hydroxyl or amine functional resins |
US5814689A (en) * | 1997-08-29 | 1998-09-29 | Arco Chemical Technology, L.P. | Low viscosity polyuretidione polyurethanes and their use as curatives for solvent and water borne coatings |
JPH11279450A (ja) * | 1998-02-02 | 1999-10-12 | Asahi Chem Ind Co Ltd | 粉体塗料用組成物 |
DE19814061A1 (de) | 1998-03-30 | 1999-10-07 | Bayer Ag | Copolymerisatdispersionen, Bindemittelkombinationen auf Basis der Copolymerisatdispersionen, ein Verfahren zu deren Herstellung und deren Verwendung |
DE19854405B4 (de) * | 1998-11-25 | 2016-05-04 | Basf Se | Kompakte Kaschierung auf der Basis von Polyisocyanat-Polyadditionsprodukten |
GB9828446D0 (en) * | 1998-12-24 | 1999-02-17 | Ici Plc | Coating composition |
DE19903391A1 (de) | 1999-01-29 | 2000-08-03 | Bayer Ag | Wäßriges Überzugsmittel, Verfahren zu seiner Herstellung und seine Verwendung |
DE19929064A1 (de) * | 1999-06-25 | 2000-12-28 | Bayer Ag | Verfahren zur Herstellung Uretdiongruppen aufweisender Polyadditionsverbindungen |
EP1106613B1 (de) * | 1999-12-07 | 2002-04-10 | Chinese Petroleum Corporation | Uretedionderivat, es enthaltende härtbare Harzzusammensetzung und Verfahren zu seiner Herstellung |
DE60116825T2 (de) * | 2000-10-13 | 2006-07-27 | Tosoh Corp., Shinnanyo | Katalysator zur Herstellung von einer Zwei-Komponenten Polyurethandichtungsmasse |
DE10123417A1 (de) | 2001-05-14 | 2002-11-21 | Bayer Ag | Verfahren zur Dimerisierung von Isophorondiisocyanat |
CA2491459C (en) | 2002-07-04 | 2012-04-03 | Bayer Materialscience Ag | Polyadducts containing uretdione groups |
DE10234792A1 (de) * | 2002-07-31 | 2004-02-12 | Basf Coatings Ag | Strukturviskose Klarlack-Slurry, Verfahren zu ihrer Herstellung und ihre Verwendung |
ITVA20020064A1 (it) * | 2002-12-02 | 2004-06-03 | Lamberti Spa | Dispersioni acquose stabili di poliisocianati bloccati non ionici. |
JP4143825B2 (ja) * | 2003-01-28 | 2008-09-03 | 三菱瓦斯化学株式会社 | ポリイソシアネート化合物、その製造方法、重付加組成物、および粉体塗料 |
DE10320267A1 (de) * | 2003-05-03 | 2004-11-18 | Degussa Ag | Bei niedriger Temperatur härtbare feste uretdiongruppenhaltige Polyurethan-Pulverlackzusammensetzungen |
DE10347902A1 (de) * | 2003-10-15 | 2005-05-19 | Degussa Ag | Feste uretdiongruppenhaltige Polyadditionsverbindungen |
DE10347901A1 (de) * | 2003-10-15 | 2005-05-19 | Degussa Ag | Polyurethan-Pulverlackbeschichtungen, welche feste uretdiongruppenhaltige Polyadditionsverbindungen enthalten, und ein Verfahren zu ihrer Herstellung |
DE10348966A1 (de) | 2003-10-22 | 2005-06-02 | Degussa Ag | Hochreaktive Polyurethan-Pulverlackzusammensetzungen auf Basis epoxidgruppenterminierter, uretdiongruppenhaltiger Polyadditionsverbindungen |
US20050113552A1 (en) | 2003-11-25 | 2005-05-26 | Tazzia Charles L. | Method for making an aqueous coating with a solid crosslinking agent |
DE102004012903A1 (de) * | 2004-03-17 | 2005-10-06 | Bayer Materialscience Ag | Niedrigviskose Allophanate mit aktinisch härtbaren Gruppen |
DE102004020429A1 (de) * | 2004-04-27 | 2005-11-24 | Degussa Ag | Uretdiongruppenhaltige Polyurethanzusammensetzungen, welche bei niedriger Temperatur härtbar sind und (teil-)kristalline Harze enthalten |
DE102004020451A1 (de) * | 2004-04-27 | 2005-12-01 | Degussa Ag | Uretdiongruppenhaltige Polyurethanzusammensetzungen, welche bei niedriger Temperatur härtbar sind und (teil-)kristalline Harze enthalten |
US7485729B2 (en) * | 2004-08-12 | 2009-02-03 | King Industries, Inc. | Organometallic compositions and coating compositions |
WO2006022899A2 (en) * | 2004-08-12 | 2006-03-02 | King Industries, Inc. | Organometallic compositions and coating compositions |
DE102004043540A1 (de) * | 2004-09-09 | 2006-03-30 | Bayer Materialscience Ag | Niedrigviskose Allophanate mit aktinisch härtbaren Gruppen |
DE102004043538A1 (de) * | 2004-09-09 | 2006-03-16 | Bayer Materialscience Ag | Herstellung von neuen strahlenhärtenden Bindemitteln |
DE102004048773A1 (de) * | 2004-10-07 | 2006-04-13 | Degussa Ag | Hydroxylterminierte uretdiongruppenhaltige Polyurethanverbindungen |
DE102004049592A1 (de) * | 2004-10-12 | 2006-05-04 | Bayer Materialscience Ag | Mit Soft-Touch-Lack beschichtete, verformbare Kunststoffverbundfolien und Kunststoffverbundelemente sowie deren Herstellung |
US7135505B2 (en) * | 2004-10-25 | 2006-11-14 | Bayer Materialscience Llc | Radiation curable coatings based on uretdione polyisocyanates |
EP1833869B1 (de) * | 2004-12-15 | 2008-10-01 | Akzo Nobel Coatings International BV | Thiolfunktionelle verbindungen enthaltende wässrige beschichtungszusammensetzung |
DE102004062588A1 (de) * | 2004-12-24 | 2006-07-06 | Degussa Ag | Hochreaktive uretdiongruppenhaltige Polyurethanzusammensetzungen auf Basis von 1,4-Diisocyanatocyclohexylmethan |
DE102005013329A1 (de) * | 2005-03-23 | 2006-11-16 | Degussa Ag | Niedrigviskose uretdiongruppenhaltige Polyadditionsverbindungen, Verfahren zur Herstellung und Verwendung |
DE102005013401A1 (de) * | 2005-03-23 | 2006-09-28 | Degussa Ag | Niedrigviskose uretdiongruppenhaltige Polyadditionsverbindungen, Verfahren zur Herstellung und Verwendung |
DE102005019430A1 (de) * | 2005-04-25 | 2006-10-26 | Bayer Materialscience Ag | N-Methylpyrrolidon-freie Polyurethan-Dispersionen auf Basis von Dimethylolpropionsäure |
DE102005036654A1 (de) | 2005-08-04 | 2007-02-15 | Bayer Materialscience Ag | Selbstvernetzende PUR-Dispersionen mit Uretdionstruktur |
DE102005049916A1 (de) * | 2005-10-17 | 2007-04-19 | Degussa Gmbh | Lagerstabile, reaktive Pulverlackzusammensetzungen mit kristallinen Bestandteilen |
DE102005053678A1 (de) * | 2005-11-10 | 2007-05-16 | Bayer Materialscience Ag | Hydrophile Polyisocyanatgemische |
DE102005060828A1 (de) * | 2005-12-20 | 2007-06-28 | Bayer Materialscience Ag | Verfahren zur Herstellung von Polyadditionsverbindungen |
DE102006042494A1 (de) * | 2006-09-07 | 2008-03-27 | Evonik Degussa Gmbh | Bei niedriger Temperatur härtbare, uretdiongruppenhaltige Polyurethanzusammensetzungen mit quartären Ammoniumhalogeniden |
DE102006046368A1 (de) * | 2006-09-29 | 2008-04-03 | Construction Research & Technology Gmbh | Funktionalisiertes Polyurethanharz, Verfahren zu seiner Herstellung sowie dessen Verwendung |
DE102007040239A1 (de) * | 2007-08-25 | 2009-05-07 | Bayer Materialscience Ag | Verfahren zur Herstellung von niedrigviskosen Allophanaten mit aktinisch härtbaren Gruppen |
DE102008007386A1 (de) | 2008-02-01 | 2009-08-06 | Evonik Degussa Gmbh | Verfahren zur Herstellung hochreaktiver uretdiongruppenhaltiger Polyurethanzusammensetzungen im Dryblend |
EP2257580B1 (de) * | 2008-03-20 | 2012-03-07 | Basf Se | Polyurethansysteme für die herstellung von polyurethan-sandwichteilen bei geringen formtemperaturen |
EP2110396A1 (de) * | 2008-04-18 | 2009-10-21 | Bayer MaterialScience AG | 1K-PUR-Systeme aus wässrigen oder wasserlöslichen Polyurethanen |
EP2110395A1 (de) * | 2008-04-18 | 2009-10-21 | Bayer MaterialScience AG | Wässrige Polyurethanlösungen für Polyurethan-Systeme |
DE102008002703A1 (de) * | 2008-06-27 | 2009-12-31 | Evonik Degussa Gmbh | Hochreaktive, Uretdiongruppen haltige Polyurethanzusammensetzungen, die metallfreie Acetylacetonate enthalten |
DE102008040967A1 (de) * | 2008-08-04 | 2010-02-11 | Leibniz-Institut Für Polymerforschung Dresden E.V. | Werkstoff-Kunststoff-Verbunde und Verfahren zu ihrer Herstellung |
DE102009008950A1 (de) * | 2009-02-13 | 2010-08-19 | Bayer Materialscience Ag | Wässrige Beschichtungssysteme auf Basis physikalisch trocknender Urethanacrylate |
DK2236533T3 (da) * | 2009-03-31 | 2012-02-20 | Sika Technology Ag | Varmehærdende eller varmeaktiverbar sammensætning indeholdende et overfladeaktiveret polyisocyanat |
US20110045219A1 (en) * | 2009-08-18 | 2011-02-24 | Bayer Materialscience Llc | Coating compositions for glass substrates |
US9080074B2 (en) * | 2010-03-19 | 2015-07-14 | Bayer Materialscience Llc | Low temperature curing polyuretdione compositions |
CN102311700A (zh) * | 2010-06-29 | 2012-01-11 | 拜耳材料科技(中国)有限公司 | 脂肪族聚脲涂料、制备方法及其应用 |
KR20130143564A (ko) * | 2010-09-07 | 2013-12-31 | 바이엘 인텔렉쳐 프로퍼티 게엠베하 | 내광성 발포 폴리우레탄 성형물 |
EP2632965B1 (de) * | 2010-10-29 | 2017-04-26 | Lubrizol Advanced Materials, Inc. | Wässrige kationische polyurethandispersionen |
KR20130129231A (ko) * | 2010-12-08 | 2013-11-27 | 다우 글로벌 테크놀로지스 엘엘씨 | 섬유-보강된 플라스틱을 접합시키기 위한 2-부분 폴리우레탄 접착제 |
EP2465886A1 (de) * | 2010-12-16 | 2012-06-20 | Bayer MaterialScience AG | Polyisocyanat-Polyadditionsprodukte, ein Verfahren zu ihrer Herstellung und ihre Verwendung |
US8912113B2 (en) * | 2011-03-06 | 2014-12-16 | King Industries, Inc. | Compositions of a metal amidine complex and second compound, coating compositions comprising same |
US8841369B2 (en) * | 2011-03-30 | 2014-09-23 | Basf Se | Latently reactive polyurethane dispersion with activatable crosslinking |
WO2013043333A1 (en) * | 2011-09-21 | 2013-03-28 | Dow Global Technologies Llc | Polyurethanes made using mixtures of tertiary amine compounds and lewis acids as catalysts |
CN104470963A (zh) * | 2012-07-26 | 2015-03-25 | 拜耳材料科技股份有限公司 | 包含对苯二甲酸聚酯的水性聚氨酯分散体 |
DE102012218081A1 (de) * | 2012-10-04 | 2014-04-10 | Evonik Industries Ag | Neuartige hydrophile Polyisocyanate mit verbesserter Lagerstabilität |
US9175117B2 (en) * | 2013-03-15 | 2015-11-03 | Covestro Llc | Dual cure composite resins containing uretdione and unsaturated sites |
EP2801587A1 (de) * | 2013-05-07 | 2014-11-12 | Rhein Chemie Rheinau GmbH | Zusammensetzungen, deren Herstellung und deren Verwendung zur Herstellung von Gusspolyamiden |
US9206320B1 (en) * | 2013-07-18 | 2015-12-08 | Hentzen Coatings, Inc. | Matte-appearance powder coating compositions with chemical agent resistance |
KR102289614B1 (ko) * | 2013-11-29 | 2021-08-17 | 바스프 에스이 | 가사 시간이 길고 경화가 빠른 폴리우레탄 시스템 |
DE102014209183A1 (de) * | 2014-05-15 | 2015-11-19 | Evonik Degussa Gmbh | Reaktive Zusammensetzung aus einer Uretdiongruppen haltigen Dispersion und Polyaminen |
DE102014214130A1 (de) * | 2014-07-21 | 2016-01-21 | Evonik Degussa Gmbh | Hochreaktive, Uretdiongruppen haltige Polyurethanzusammensetzungen, die Carbonatsalze enthalten |
EP2979851A1 (de) * | 2014-07-28 | 2016-02-03 | Evonik Degussa GmbH | Effiziente Herstellung von Composite-Halbzeugen und -Bauteilen im Nasspressverfahren unter Einsatz von hydroxyfunktionalisierten (Meth) Acrylaten, die mittels Isocyanaten oder Uretdionen duroplastisch vernetzt werden |
ES2715851T3 (es) * | 2014-08-29 | 2019-06-06 | Covestro Deutschland Ag | Esteres de poli(ácido aspártico) hidrófilos |
EP2993202A1 (de) * | 2014-09-08 | 2016-03-09 | Evonik Degussa GmbH | Composite-Halbzeuge und daraus hergestellte Formteile sowie direkt hergestellte Formteile auf Basis von hydroxyfunktionalisierten (Meth)Acrylaten und Uretdionen, die duroplastisch vernetzt werden |
EP3026071A1 (de) * | 2014-11-26 | 2016-06-01 | Henkel AG & Co. KGaA | Stabilisierte Polyurethan-Dispersionen |
DK3303437T3 (da) * | 2015-05-29 | 2020-03-16 | Basf Se | Polyurethan-polyisocyanurat-harpiks til fiber-kompositmaterialer med lang åben klæbetid |
CN108699204B (zh) * | 2016-03-09 | 2020-10-16 | 旭化成株式会社 | 多异氰酸酯组合物、涂覆组合物、水系涂覆组合物和涂覆基材 |
-
2019
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