EP3768750A1 - Compositions aqueuses contenant des groupes uretdione et leur procédé de préparation - Google Patents

Compositions aqueuses contenant des groupes uretdione et leur procédé de préparation

Info

Publication number
EP3768750A1
EP3768750A1 EP19711126.3A EP19711126A EP3768750A1 EP 3768750 A1 EP3768750 A1 EP 3768750A1 EP 19711126 A EP19711126 A EP 19711126A EP 3768750 A1 EP3768750 A1 EP 3768750A1
Authority
EP
European Patent Office
Prior art keywords
diisocyanate
uretdione
polyol
groups
composition according
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
Application number
EP19711126.3A
Other languages
German (de)
English (en)
Inventor
Dorota Greszta-Franz
Saskia BEUCK
Sebastian Dörr
Hans-Josef Laas
Nusret Yuva
Heinz-Dietmar Gewiss
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Covestro Deutschland AG
Covestro LLC
Original Assignee
Covestro Intellectual Property GmbH and Co KG
Covestro LLC
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from EP18163625.9A external-priority patent/EP3543271A1/fr
Priority claimed from US15/933,487 external-priority patent/US20190292305A1/en
Priority claimed from US15/933,507 external-priority patent/US20190292294A1/en
Priority claimed from US15/933,527 external-priority patent/US20190292296A1/en
Priority claimed from US15/933,553 external-priority patent/US10633477B2/en
Priority claimed from US15/933,470 external-priority patent/US11292864B2/en
Priority claimed from US15/933,500 external-priority patent/US10696775B2/en
Priority claimed from EP18163621.8A external-priority patent/EP3543270A1/fr
Priority claimed from US15/933,570 external-priority patent/US10731051B2/en
Priority claimed from US15/933,475 external-priority patent/US11008416B2/en
Priority claimed from EP18163620.0A external-priority patent/EP3543269A1/fr
Priority claimed from US15/933,495 external-priority patent/US11312881B2/en
Priority claimed from US15/933,511 external-priority patent/US11440988B2/en
Priority claimed from EP18181876.6A external-priority patent/EP3590987A1/fr
Priority claimed from EP18181877.4A external-priority patent/EP3590988A1/fr
Application filed by Covestro Intellectual Property GmbH and Co KG, Covestro LLC filed Critical Covestro Intellectual Property GmbH and Co KG
Publication of EP3768750A1 publication Critical patent/EP3768750A1/fr
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—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
    • 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
    • C08G18/08—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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
    • C08G18/20—Heterocyclic amines; Salts thereof
    • C08G18/2045—Heterocyclic amines; Salts thereof containing condensed heterocyclic rings
    • C08G18/2063—Heterocyclic amines; Salts thereof containing condensed heterocyclic rings having two nitrogen atoms in the condensed ring system
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/18—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
    • 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
    • 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
    • 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
    • C08G18/3234—Polyamines cycloaliphatic
    • 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
    • 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
    • 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
    • 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
    • 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
    • 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
    • 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
    • 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
    • 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
    • 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
    • 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
    • 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
    • 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
    • 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
    • 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
    • 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
    • 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.
  • US 2015232609 A1 discloses water-dispersible hydrophilic uretdione-containing polyisocyanates obtainable by reacting a uretdione-bearing prepolymer with an emulsifier comprising an ionogenic group, the ionogenic 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, which is still insufficient for practical applications in industry, where not infrequently 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, more preferably based on aliphatic, and / or cycloaliphatic polyisocyanates, which are not chemically bonded containing hydrophilizing 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: 1.0 to 1.0: 2.0 and wherein (A) and (B) exist as a physical mixture.
  • Aqueous uretdione group-containing composition according to aspect 1 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 4,4'-diisocyanate (MDI), triphenylmethane-4
  • Aqueous uretdione group-containing composition according to aspect 1 or 2 characterized in that
  • Aqueous uretdione group-containing composition according to one of the preceding aspects, characterized in that
  • the at least one uretdione group-containing hardener (A) has 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.
  • 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 1 to 50 mg KOH / g, more preferably 1 to 5 mg KOH / g, preferably measured according to DIN EN ISO
  • Aqueous uretdione group-containing composition according to one of the preceding aspects, characterized in that
  • the at least one hydroxyl-containing polyol (B) which is not ionically hydrophilized is obtained by reacting
  • A3) optionally at least one polyol other than A2,
  • the at least one hydroxyl-containing polyol (B) which is not ionically hydrophilized preferably has an acid number of at most 5 mg KOH / g, determined according to DIN EN ISO 2114: 2002-06 with acetone and ethanol in a weight ratio of 2: 1 as 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 hydroxy-containing polyol (B) has an OH content greater than 1% by weight - calculated as OH group to solid content, molecular weight 17 g / mol - and / or 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, Propylene glycol mono-n-butyl ether, dipropylene glycol dimethyl ether, methoxypropyl acetate, dibasic esters or mixtures thereof.
  • Aqueous uretdione 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.
  • Aqueous uretdione group-containing composition according to one of the preceding aspects, characterized in that
  • the sum of the weight fractions of (A), (B) and (D) is from 30 to 60% by weight, based on the solids content of the total aqueous composition.
  • a process for producing a polyurethane layer comprising the steps
  • step iv) curing the mixture from step iii) with heat from 40 ° C to 180 ° C for up to 180 minutes.
  • aqueous composition containing uretdione groups was obtained by mixing the hardener (A) containing uretdione groups with the at least one polyol (B) in the absence of water and subsequent dispersion with water.
  • Polyurethane layer in particular polyurethane film, obtainable by a process according to aspect 11 or 12.
  • molecular weights are determined by GPC (gel permeation chromatography) using polystyrene standards.
  • the average molecular weight is according to this invention as the number average molecular weight Mn defined. Mn is determined at 23 ° C in tetrahydrofuran as a solvent. The measurement is carried out as described in DIN 55672-1: 2007-08 "Gel Permeation Chromatography, Part 1 - Tetrahydrofuran as Eluent" described with a SECURITY GPC system from PSS Polymer Service, flow rate 0.6 ml / min.
  • % by weight refers 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.
  • the term "at least one" refers to the nature of the compounds rather than individual molecules.
  • at least one copolymer is to be understood to contain at least one type of copolymer, but it is contained in an arbitrary number of molecules in the composition.
  • 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 uretdione group. 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-isocyanatomethyl (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 subordinate quantities may also contain individual constituents which have a molecular weight below or below this limit. These are the polyester diols known per se, which are built up from diols and dicarboxylic acids.
  • diols examples include 1,4-dimethylolcyclohexane, 1,4- or 1,3-butanediol, 1,6-hexanediol, neopentyl glycol, 2,2,4-trimethyl-1,3-pentanediol, trimethylolpropane and pentaerythritol or mixtures such 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, glut
  • 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.
  • polyol component (b2) in the preparation of uretdione groups having curing agent (A) and low molecular weight ester groups having diols of a mean, calculated from functionality and hydroxyl number molecular weight of 134 to 349 g / mol, preferably 176 to 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, phthalic, isophthalic, phthalic, tetrahydrophthalic, maleic, maleic, terephthalic
  • 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 cycloaliphatic amines and amino alcohols having 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 forming anions or cations 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 polyol (component (B)).
  • the polyol can be obtained by reacting a polyisocyanate (Al) with that with the component (A2) "optionally with the concomitant use of the polyol component (A3).
  • polyisocyanates examples include tetramethylene diisocyanate, cyclohexane-1,3- and 1,4-diisocyanate, pentamethylene diisocyanate, hexamethylene diisocyanate (HDI), 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 , 4'-diisocyanate (MDI), triphenylmethane-4,4'-diisocyanate or naphthylene-l, 5-diisocyanate and any mixtures of such
  • the component (Al) may also have isocyanurate, biuret, allophanate, urethane and / or urea structures.
  • A2 is a polyalkoxy ether derivative which has at least one, preferably two, -OH radicals; more preferably it is a compound of formula (I):
  • X is H or alkyl, preferably H or C 1-20 -alkyl, more preferably H or C 2-10 -alkyl;
  • R is a C14 alkylene radical
  • p is an integer from 2 to 50;
  • n is independently 0 or 1 and
  • n is independently 0 or 1
  • X is H, methyl, ethyl, or propyl, preferably ethyl;
  • R is methyl
  • p is an integer of 5 to 25;
  • n is independently 0 or 1 and
  • n is independently 0 or 1
  • n or m in each unit p is equal to 1 and the number of n> m, preferably the total number of n is at least 2 * m, more preferably n is at least 3 * m, am most preferably, only n is present.
  • Suitable compounds A3 are selected from at least one polyol other than A2, preferably selected from polyesterpolyols, polyetherpolylenes, polyurethanepolyols, polyacrylatepolyols, polymethacrylatepolyols, polycarbonatepolyols or mixtures thereof, more preferably A3 selected from polyesterpolyols, polyetherpolyols, polycarbonatepolyols, polyurethanepolyols, polyacrylatepolyols, Polymethacrylate polyols, C 2 -C 10 hydrocarbons having at least two hydroxy radicals, or mixtures thereof, more preferably A3 is a polyester polyol.
  • Preferred compounds for A3 are the compounds described above under (bl) and (b2), respectively.
  • polyol (B) is prepared from 5 to 80 wt .-%, preferably 10 to 60 wt .-% component (Al),
  • the preparation of the polyurethane resin used according to the invention is preferably carried out in such a way that one see a polyol (B) with at least one uretdione curing agent (A), based on aliphatic, (cyclo) aliphatic, araliphati see and / or aromatic polyisocyanates, which no chemically bonded hydrophilizing Groups homogeneously mixed in non-aqueous system and dispersed with deionized water.
  • A uretdione curing agent
  • solvents under (C) all liquid substances are suitable which do not react with other ingredients. Preference is given to 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. Optionally, 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. Examples:
  • Ymer N 120 - a linear, difunctional TMP-started polyethylene glycol monomethyl ether having an OH number of 100-120 mg KOH / g, available from Perstorp
  • 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 from Malvern (DE) according to DIN ISO 13321: 2004-10. 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.
  • the dispersion remained stable for 5 months at 23 ° C.
  • the dispersions were mixed in a speed mixer at 2000 rpm for 1 minute and applied to a coil metal plate with a doctor blade having a layer thickness of 180 ⁇ m (wet).
  • the plates with the applied wet paints were flashed for 5 min at room temperature, baked for 30 min at 180 ° C and then stored for 4 days at room temperature.
  • the stored films were evaluated by application technology (Table 2).
  • the uretdione-containing dispersions according to the invention give hard and stable fack.
  • IPDI with a content of free isocyanate groups of 17.0% and a calculated content of uretdione groups of 20.8% were heated to 80 ° C. under dry nitrogen and admixed with 500 g (1.00 eq) of methoxypolyethylene glycol 500. It was then stirred at a reaction temperature of max. 70 ° C until the NCO content of the reaction mixture had dropped to a value of less than 0.1%. There was a pale yellow colored liquid, which was then dispersed in the water to 30 wt .-% solids content, filled into a 500 ml bottle with a water-filled riser and allowed to stand at 23 ° C. In the riser, a volume displacement of water was already observed after one day, which points to CO2 evolution and thus to a poor storage stability of the hydrophilicized uretdione group-containing polyisocyanate (Table 3).

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  • Organic Chemistry (AREA)
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Abstract

La présente invention concerne des compositions aqueuses contenant des groupes uretdione, renfermant ou étant constituées par (A) au moins un durcisseur contenant des groupes uretdione, à base de polyisocyanates aliphatiques, cycloaliphatiques, araliphatiques et/ou aromatiques qui ne contiennent pas de groupes hydrophiles liés chimiquement ; (B) au moins un polyol contenant des groupes hydroxy, qui n'est pas hydrophilisé par voie ionique ; (C) éventuellement des solvants ; et (D) éventuellement des adjuvants et des additifs, le rapport quantitatif des constituants (A) et (B) étant calculé de sorte que le rapport molaire entre les groupes NCO présents sous forme d'uretdione du durcisseur (A) et les groupes réactifs NCO du polyol (B) étant de 3:0,5 à 0,5:3, A et B se présentant sous la forme d'un mélange physique. L'invention concerne en outre un procédé de fabrication d'une couche de polyuréthane par utilisation de la composition aqueuse contenant des groupes uretdione de la présente invention, la couche de polyuréthane ainsi obtenue, ainsi qu'un substrat revêtu de cette couche de polyuréthane ou collé à celle-ci.
EP19711126.3A 2018-03-23 2019-03-21 Compositions aqueuses contenant des groupes uretdione et leur procédé de préparation Pending EP3768750A1 (fr)

Applications Claiming Priority (16)

Application Number Priority Date Filing Date Title
US15/933,487 US20190292305A1 (en) 2018-03-23 2018-03-23 Uretdione based polyurethane compositions
EP18163620.0A EP3543269A1 (fr) 2018-03-23 2018-03-23 Dispersions de polyuréthane contenant de l'uretdione comprenant des groupes hydrophiles
US15/933,553 US10633477B2 (en) 2018-03-23 2018-03-23 Extended pot-life for low temperature curing polyuretdione resins
US15/933,470 US11292864B2 (en) 2018-03-23 2018-03-23 Compositions using polyuretdione resins
US15/933,500 US10696775B2 (en) 2018-03-23 2018-03-23 Curing for polyallophanate compositions through undercoat acid neutralization
EP18163621.8A EP3543270A1 (fr) 2018-03-23 2018-03-23 Système catalyseur pour dispersions d'uretdions
EP18163625.9A EP3543271A1 (fr) 2018-03-23 2018-03-23 Compositions aqueuses contenant des groupes urétdione et son procede de fabrication
US15/933,507 US20190292294A1 (en) 2018-03-23 2018-03-23 One component allophanate formulations through basecoat catalyst migration
US15/933,527 US20190292296A1 (en) 2018-03-23 2018-03-23 Polyol acid neutralization for low temperature uretdione curing
US15/933,495 US11312881B2 (en) 2018-03-23 2018-03-23 One component polyurethane/allophanate formulations with reactive reducer
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
US15/933,570 US10731051B2 (en) 2018-03-23 2018-03-23 Basecoat acid neutralization through inorganic salts
EP18181876.6A EP3590987A1 (fr) 2018-07-05 2018-07-05 Compositions aqueuses contenant des groupes urétdione et leur procédé de production
EP18181877.4A EP3590988A1 (fr) 2018-07-05 2018-07-05 Compositions aqueuses contenant des groupes urétdione et leur procédé de production
PCT/EP2019/057065 WO2019180128A1 (fr) 2018-03-23 2019-03-21 Compositions aqueuses contenant des groupes uretdione et leur procédé de préparation

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EP19713339.0A Pending EP3768752A1 (fr) 2018-03-23 2019-03-21 Neutralisation d'acide de couche de fond au moyen de sels inorganiques
EP19711125.5A Pending EP3768749A1 (fr) 2018-03-23 2019-03-21 Compositions aqueuses contenant des groupes uretdione et leur procédé de préparation
EP19711129.7A Pending EP3768751A1 (fr) 2018-03-23 2019-03-21 Compositions aqueuses contenant des groupes uretdione et procédé pour leur préparation
EP19713663.3A Withdrawn EP3768747A1 (fr) 2018-03-23 2019-03-21 Composition aqueuse durcissable comprenant un prépolymère d'urétdione dispersé, un réactif et un azolate
EP19711128.9A Withdrawn EP3768745A1 (fr) 2018-03-23 2019-03-21 Dispersions de polyuréthane contenant de l'urétdione comprenant des groupes hydrophiles
EP19713666.6A Withdrawn EP3768754A1 (fr) 2018-03-23 2019-03-21 Compositions de mélange de résines contenant des polyuretdione
EP19713669.0A Withdrawn EP3768757A1 (fr) 2018-03-23 2019-03-21 Formulations d'allophanate à un composant par migration de catalyseur de couche de base
EP19714972.7A Withdrawn EP3768759A1 (fr) 2018-03-23 2019-03-21 Durée de vie en pot prolongée pour des résines polyurétdione à durcissement à basse température
EP19713668.2A Pending EP3768756A1 (fr) 2018-03-23 2019-03-21 Neutralisation d'acide polyol pour durcissement d'urétdione à basse température
EP19713667.4A Withdrawn EP3768755A1 (fr) 2018-03-23 2019-03-21 Compositions utilisant des résines polyurétdione
EP19713670.8A Withdrawn EP3768758A1 (fr) 2018-03-23 2019-03-21 Formulations de polyuréthane/allophanate à un seul composant comprenant un réducteur réactif
EP19711126.3A Pending EP3768750A1 (fr) 2018-03-23 2019-03-21 Compositions aqueuses contenant des groupes uretdione et leur procédé de préparation
EP19713665.8A Withdrawn EP3768753A1 (fr) 2018-03-23 2019-03-21 Durcissement amélioré de compositions de polyallophanate par neutralisation de l'acide de sous-couche
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EP19713339.0A Pending EP3768752A1 (fr) 2018-03-23 2019-03-21 Neutralisation d'acide de couche de fond au moyen de sels inorganiques
EP19711125.5A Pending EP3768749A1 (fr) 2018-03-23 2019-03-21 Compositions aqueuses contenant des groupes uretdione et leur procédé de préparation
EP19711129.7A Pending EP3768751A1 (fr) 2018-03-23 2019-03-21 Compositions aqueuses contenant des groupes uretdione et procédé pour leur préparation
EP19713663.3A Withdrawn EP3768747A1 (fr) 2018-03-23 2019-03-21 Composition aqueuse durcissable comprenant un prépolymère d'urétdione dispersé, un réactif et un azolate
EP19711128.9A Withdrawn EP3768745A1 (fr) 2018-03-23 2019-03-21 Dispersions de polyuréthane contenant de l'urétdione comprenant des groupes hydrophiles
EP19713666.6A Withdrawn EP3768754A1 (fr) 2018-03-23 2019-03-21 Compositions de mélange de résines contenant des polyuretdione
EP19713669.0A Withdrawn EP3768757A1 (fr) 2018-03-23 2019-03-21 Formulations d'allophanate à un composant par migration de catalyseur de couche de base
EP19714972.7A Withdrawn EP3768759A1 (fr) 2018-03-23 2019-03-21 Durée de vie en pot prolongée pour des résines polyurétdione à durcissement à basse température
EP19713668.2A Pending EP3768756A1 (fr) 2018-03-23 2019-03-21 Neutralisation d'acide polyol pour durcissement d'urétdione à basse température
EP19713667.4A Withdrawn EP3768755A1 (fr) 2018-03-23 2019-03-21 Compositions utilisant des résines polyurétdione
EP19713670.8A Withdrawn EP3768758A1 (fr) 2018-03-23 2019-03-21 Formulations de polyuréthane/allophanate à un seul composant comprenant un réducteur réactif

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EP19713665.8A Withdrawn EP3768753A1 (fr) 2018-03-23 2019-03-21 Durcissement amélioré de compositions de polyallophanate par neutralisation de l'acide de sous-couche
EP19711127.1A Withdrawn EP3768748A1 (fr) 2018-03-23 2019-03-21 Système catalytique pour dispersions d'uretdione

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Families Citing this family (2)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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
NL265610A (fr) 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
DE69026570T2 (de) 1989-10-03 1996-10-31 Asahi Glass Co 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 (fr) * 1990-07-30 2003-09-30 Terry A. Potter Revetement de polyurethanne a deux elements en dispersion aqueuse
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 (fr) 1993-11-11 2005-03-08 Oleg Werbitzky Amidines bicycliques, methode pour leur obtention et leur utilisation comme catalyseur
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
DE69531847T2 (de) * 1994-06-06 2004-08-05 Basf Corp. Aldimin und Isocyanat enthaltende Beschichtungszusammensetzungen sowie Verfahren zu deren Herstellung
US5523376A (en) * 1994-12-21 1996-06-04 Bayer Corporation Coating compositions based on aldimines and polyisocyanates containing uretdione groups
CA2245730C (fr) * 1996-02-17 2006-01-03 Imperial Chemical Industries Plc Composition de revetement
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
DE69901260T2 (de) * 1999-12-07 2002-08-14 Chinese Petroleum Corp 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
BR0305352B1 (pt) 2002-07-04 2012-08-21 isocianato apresentando grupos uretodiona, seu processo de dimerização e suas aplicações.
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
US20060036007A1 (en) * 2004-08-12 2006-02-16 King Industries, Inc. Organometallic compositions and coating compositions
DE102004043538A1 (de) * 2004-09-09 2006-03-16 Bayer Materialscience Ag Herstellung von neuen strahlenhärtenden Bindemitteln
DE102004043540A1 (de) * 2004-09-09 2006-03-30 Bayer Materialscience Ag Niedrigviskose Allophanate mit aktinisch härtbaren Gruppen
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
CN101080429B (zh) * 2004-12-15 2010-10-13 阿克佐诺贝尔国际涂料股份有限公司 包含硫醇官能化合物的水基涂料组合物
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 (fr) * 2008-03-20 2012-03-07 Basf Se Systèmes polyuréthanne pour la fabrication de pièces sandwichs en polyuréthanne à des températures de moule faibles
EP2110395A1 (fr) * 2008-04-18 2009-10-21 Bayer MaterialScience AG Solutions de polyuréthane aqueuses pour systèmes de polyuréthane
EP2110396A1 (fr) * 2008-04-18 2009-10-21 Bayer MaterialScience AG Systèmes 1K-PUR en polyuréthanes aqueux ou solubles dans l'eau
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
CN103314043B (zh) * 2010-09-07 2015-07-08 拜耳知识产权有限责任公司 发泡耐光聚氨酯成型件
KR20140004091A (ko) * 2010-10-29 2014-01-10 루브리졸 어드밴스드 머티어리얼스, 인코포레이티드 수성의 양이온성 폴리우레탄 분산물
BR112013013865A2 (pt) * 2010-12-08 2016-09-13 Dow Global Technologies Llc sistema adesivo de poliuretano de dois componentes e processo para colar um par de substratos
EP2465886A1 (fr) * 2010-12-16 2012-06-20 Bayer MaterialScience AG Produits de polyaddition de polyisocyanate, leur procédé de fabrication et d'utilisation
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
US9969837B2 (en) * 2011-09-21 2018-05-15 Dow Global Technologies Llc Polyurethanes made using mixtures of tertiary amine compounds and lewis acids as catalysts
WO2014016294A1 (fr) * 2012-07-26 2014-01-30 Bayer Materialscience Ag Dispersion aqueuse de polyuréthane comprenant un polyester d'acide téréphtalique
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 (fr) * 2013-05-07 2014-11-12 Rhein Chemie Rheinau GmbH Compositions, leur fabrication et leur utilisation pour la fabrication de polyamides de fonte
US9206320B1 (en) * 2013-07-18 2015-12-08 Hentzen Coatings, Inc. Matte-appearance powder coating compositions with chemical agent resistance
RU2667525C9 (ru) * 2013-11-29 2018-12-12 Басф Се Полиуретановая система с длительным временем обработки и быстрым отверждением
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 (fr) * 2014-07-28 2016-02-03 Evonik Degussa GmbH Fabrication efficace de demi-produits et composants composites dans le cadre du procédé de pressage à froid utilisant des (méth)acrylates hydroxyfonctionnalisés réticulés par duroplastie à l'aide d'isocyanates ou d'uretdions
EP2990398B1 (fr) * 2014-08-29 2018-12-19 Covestro Deutschland AG Ester d'acide polyasparaginique hydrophile
EP2993202A1 (fr) * 2014-09-08 2016-03-09 Evonik Degussa GmbH Demi-produits composites et pièces moulées en étant constituées ainsi que pièces moulées directement fabriquées à base de (méth)acrylates hydroxyfonctionnalisés et d'uretdions réticulés par duroplastie
EP3026071A1 (fr) * 2014-11-26 2016-06-01 Henkel AG & Co. KGaA Dispersions de polyuréthane stabilisées
WO2016193020A1 (fr) * 2015-05-29 2016-12-08 Basf Se Résine à base de polyisocyuranate-polyuréthane pour matériaux composites renforcés par des fibres à temps ouvert long
EP3428207B1 (fr) * 2016-03-09 2019-11-13 Asahi Kasei Kabushiki Kaisha Composition de polyisocyanate, composition de revêtement, composition de revêtement aqueux et substrat revêtu

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WO2019183323A1 (fr) 2019-09-26
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CN112105665A (zh) 2020-12-18
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CN112004853B (zh) 2023-07-28
EP3768752A1 (fr) 2021-01-27
EP3768756A1 (fr) 2021-01-27
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CN111886273A (zh) 2020-11-03

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