EP3768751A1 - Compositions aqueuses contenant des groupes uretdione et procédé pour leur préparation - Google Patents

Compositions aqueuses contenant des groupes uretdione et procédé pour leur préparation

Info

Publication number
EP3768751A1
EP3768751A1 EP19711129.7A EP19711129A EP3768751A1 EP 3768751 A1 EP3768751 A1 EP 3768751A1 EP 19711129 A EP19711129 A EP 19711129A EP 3768751 A1 EP3768751 A1 EP 3768751A1
Authority
EP
European Patent Office
Prior art keywords
uretdione
diisocyanate
groups
acid
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
EP19711129.7A
Other languages
German (de)
English (en)
Inventor
Dorota Greszta-Franz
Saskia BEUCK
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 US15/933,495 external-priority patent/US11312881B2/en
Priority claimed from US15/933,527 external-priority patent/US20190292296A1/en
Priority claimed from US15/933,500 external-priority patent/US10696775B2/en
Priority claimed from EP18163625.9A external-priority patent/EP3543271A1/fr
Priority claimed from EP18163620.0A external-priority patent/EP3543269A1/fr
Priority claimed from US15/933,570 external-priority patent/US10731051B2/en
Priority claimed from US15/933,507 external-priority patent/US20190292294A1/en
Priority claimed from EP18163621.8A external-priority patent/EP3543270A1/fr
Priority claimed from US15/933,553 external-priority patent/US10633477B2/en
Priority claimed from US15/933,487 external-priority patent/US20190292305A1/en
Priority claimed from US15/933,475 external-priority patent/US11008416B2/en
Priority claimed from US15/933,511 external-priority patent/US11440988B2/en
Priority claimed from US15/933,470 external-priority patent/US11292864B2/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 EP3768751A1 publication Critical patent/EP3768751A1/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 polyacrylate copolymer (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 lacquers and coating agents have risen sharply due to ever stricter emulsion strains with regard to the solvents released in the paint application.
  • 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 coating compositions to be processed from an aqueous phase have become known on the basis of polyurethane, which satisfies the high demands of practice to a sufficient extent.
  • 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 generally known that the epoxy varnishes are inferior to the polyurethane varnishes in most properties. According to 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.
  • EP 1687354 A1 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.
  • 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 2015232609A1 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 the 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 not infrequently long transport distances must be expected.
  • the above problems have been solved by the use of a physical mixture of the specific hardener and the polyacrylate copolymer of the present invention.
  • dispersions could be obtained which have an increased storage stability compared to the compositions known in the prior art.
  • 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 ratio of 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 polyacrylate copolymer (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 hardener (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), 1-isocyanato-3,3,5-trimethyl-5-i so cyanoatomethyl cy clohexane (isophorone diisocyanate IPDI), dicyclohexylmethane-2,4'- and / or 4,4'-diisocyanate, tetramethylxylylene diisocyanate (TMXDI), Trii so cy anatononan, T oluylenediisocyanat (TDI), diphenylmethane-2,4'- and / or 4,4'-diisocyanate
  • Aqueous uretdione group-containing composition according to aspect 1 or 2 characterized in that as feedstocks for the at least one uretdione group-containing hardener (A) hydroxyl-containing monomers and / or polymers are used.
  • 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 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 polyacrylate copolymer (B) is obtained by reacting a mixture of free-radically polymerizable monomers (M) comprising or consisting of (Ml) hydroxyl and carboxyl-free (meth) acrylic esters with CI to CI 2 hydrocarbon radicals in the alcohol unit;
  • (M4) optionally vinyl esters of aliphatic carboxylic acids
  • (M5) optionally at least one cycloaliphatic ester of (meth) acrylic acid and / or vinylaromatics.
  • Aqueous uretdione group-containing composition according to one of the preceding aspects, characterized in that
  • the at least one hydroxyl group-containing polyacrylate copolymer (B) has an OH content of more than 1% by weight - calculated as OH group to solid content, molecular weight 17 g / mol - and a number average molecular weight Mn of 500 to 20,000 g / mol. 8.
  • Aqueous uretdione according to one of the preceding aspects, characterized in that the solvent title is selected from acetone, methyl ethyl ketone, ethyl acetate, butyl acetate, xylene, heavy benzene, such as the commercially available Solvesso 100 or Solvesso 150, propyl englykolmono-n-butyl ether, dipropylene glycol dimethyl ether, methoxypropyl acetate, dibasic esters or mixtures thereof.
  • 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.
  • Aqueous uretdione group-containing composition according to one of the preceding aspects, characterized in that
  • aqueous composition containing uretdione groups has been obtained by mixing the uretdione group-containing dyeing agent (A) with the at least one polyacrylate copolymer (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.
  • the average molecular weight according to this invention is defined as the number average molecular weight Mn.
  • Mn is determined at 23 ° C in tetrahydrofuran as the solvent. The measurement is carried out as described in DIN 55672-1: 2007-08 "Gel Permeation Chromatography, Part 1 - Tetrahydrofuran as Eluent" with a SECURITY GPC System from PSS Polymer Service, flow rate 0.6 ml / min.
  • 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.
  • 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, a portion of the isocyanate groups in Ur etdiongrupp s transferred.
  • DMAP 4-dimethylaminopyridine
  • Isocyanates (a1) from which the uretdione-containing building blocks are built up, 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 tolylene diisocyanate
  • MDI diphenylmethane-2,4'- and / or 4,4'-diisocyanate
  • MDI tripfaenylmethane-4,4'-diisocyanate or naphthylene-1, 5-diisocyanate and any mixtures of such isocyanates.
  • component (A) may also have isocyanurate, biuret, allophanate, urethane and / or hamsto ff structures.
  • reaction of these uretdione group-bearing polyisocyanates to uretdione groups having Hartem (A) involves the reaction of the free NCO groups of the above 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) preferably comprises at least one diol containing ester groups and having a molecular weight Mn of from 350 to 4000 g / mol, preferably from 350 to 2000 g / mol, more preferably from 350 to 1000 g / mol.
  • the ester diols are mixtures in which, in minor amounts, individual constituents may also be present which have a molecular weight below or above these limits.
  • 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 its 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 are 1,4- or 1,3-butanediol, 1,6-hexanediol or trimethylolpropane and mixtures thereof.
  • 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 a starter, and lactones such as .beta.-propiolactone, g-butyrolactone, g- and d-valerolactone, e-caprolactone, 3,5,5- and 3,3,5-T rimethylcaprolacton or any mixtures thereof Lactones have been produced. Particularly preferred are those polycaprolactone diols which have been prepared by polymerization of e-caprolactone.
  • 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.
  • these are, for example, the per se known ester groups having diols or mixtures of such diols, such as by reaction of alcohols with minor amounts of dicarboxylic acids, corresponding Di carbonklareanhydriden, corresponding Dicarbonklam create lower alcohols or lactones h.
  • Suitable acids are succinic acid, adipic acid, sebacic acid, phthalic acid, isophthalic acid, phthalic anhydride, tetrahydrophthalic acid, maleic acid, maleic anhydride, dimethyl maleate and terephthalic acid bis-glycol ester.
  • Suitable lactones for the preparation of these ester diols are, for example, ⁇ -propiolactone, g-butyrolactone, g- and d-valerolactone, ⁇ -caprolactone, 3,5,5- and 3,3,5-trimethyl-caprolactone or any desired mixtures of such lactones.
  • Uretdiongrupp en having hardener (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, di ethyl entriamin, Ethanolamine, aminoethyl-ethanolamine, diaminocyclohexane, hexamethylenediamine, methyliminobispropylamine, iminobispropylamine, bis (aminopropyl) piperazine, aminoethylpiperazine, 1,2-diaminocyclohexane, triethyl-entetramine, tetraethylpentamine, bis (4-amino-cyclohexyl) methane, bis (4-amino
  • 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, ethyl 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 the expert understands groups that have an ability for anion or cation formation.
  • 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,
  • Dihydroxy succinic acid, or polyhydroxy acids, such as gluconic acid Dihydroxy succinic acid, or polyhydroxy acids, such as gluconic 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 curing agents (A) having primary groups are likewise preferably free of anionic sulfonic acid groups.
  • 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 hardeners (A) are furthermore preferably free of 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 polyalkyleneoxy polyethylenes 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 polyacrylate copolymer (component (B)).
  • polyacrylate copolymer 1 encompasses both polyacrylate copolymers and poly (meth) acrylate copolymers.
  • Suitable polyacrylate copolymers can be obtained, for example, by the synthesis of the following mixture of radically polymerizable monomers (M):
  • (M4) optionally vinyl esters of aliphatic carboxylic acids
  • (M5) optionally at least one cycloaliphatic ester of (meth) acrylic acid and / or vinylaromatics.
  • the mixture may further optionally contain polyols (PO) selected from the group of polyester polyols and / or polycarbonate polyols, wherein the polyols have a mean Hy droxylgrupp enfunktionloisries of at least 2.
  • PO polyols
  • the polyacrylate dispersions according to the invention can have high hydroxyl group contents, so that, without being bound by theory, a higher degree of crosslinking and thus higher hardness of the coatings can be achieved.
  • acrylic acid or methacrylic acid are also referred to as (meth) acrylic acid.
  • hydroxyl and carboxyl free monomers are used acrylates and methacrylates having 1 to 18 carbon atoms in the alcohol part of the ester group.
  • the alcohol moiety is preferably aliphatic and may be linear or branched.
  • Suitable monomers of component (III) are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, the isomeric pentyl, hexyl, 2-ethylhexyl , Octyl and dodecyl (meth) acrylates.
  • Preferred monomers (Ml) are methyl, n-butyl, isobutyl, tert-butyl (meth) acrylate and 2-ethylhexyl acrylate and styrene.
  • Suitable hydroxy-functional monomers are ethylenically unsaturated, hydroxyl-containing monomers such as hydroxyalkyl esters of unsaturated carboxylic acids, preferably hydroxyalkyl (meth) acrylates having 2 to 12, preferably 2 to 6 carbon atoms in the hydroxyalkyl radical. Examples of particularly preferred compounds are 2-
  • Hydroxy ethyl (meth) acrylate the isomeric hydroxypropyl (meth) acryl late, 2, 3 and 4 Hydroxybutyl (meth) acrylates and the isomeric hydroxyhexyl (meth) acrylates.
  • Suitable carboxyl-functional free-radically polymerizable monomers are olefinically unsaturated monomers containing carboxylic acid or carboxylic anhydride groups, such as acrylic acid, methacrylic acid, beta-carboxyethyl acrylate, crotonic acid, fumaric acid, maleic anhydride, itaconic acid or monoalkyl esters of dibasic acids or anhydrides, such as maleic acid monoalkyl esters. Acrylic acid and / or methacrylic acid are preferred.
  • Suitable vinyl esters of aliphatic carboxylic acids may be included.
  • these monomers are the esterification products of vinyl alcohol with linear or branched, aliphatic carboxylic acids such as vinyl acetate, vinyl propionate, vinyl butyrate, vinyl 2-ethylhexanoate, vinyl octanoate, vinyl decanoate, vinyl neodecanoate, vinyl dodecanoate (vinyl laurate) or vinyl stearate.
  • Suitable monomers (M5) are, for example, cyclohexyl (meth) acrylate, alkyl group-substituted cyclohexyl (meth) acrylates, 4-tert-butylcyclohexyl (meth) acrylate,
  • Suitable alkylene oxides preferably include ethylene oxide or mixtures of ethylene oxide and propylene oxide.
  • the hydrophilization of the copolymers is carried out by ionic groups, ie monomers (M3).
  • the proportions of the monomers (III) to (M6) can be selected such that the polyacrylate copolymer has an OH number (DIN EN ISO 4629-1: 2016-12) of 50 to 400 mg KOH / g, preferably from 100 to 300 mg KOH / g solids.
  • the polyester polyols and / or polycarbonate polyols (PO) it is preferred that the average hydroxyl group functionality be at least 2.5.
  • Suitable polyester polyols are the known polycondensates of poly (tri, tetra) ols and di- and optionally poly (tri, tetra) - carboxylic acids or hydroxycarboxylic acids or lactones.
  • polyesters instead of the free polycarboxylic acids, it is also possible to use the corresponding polycarboxylic anhydrides or corresponding polycarboxylic acid esters of lower alcohols to prepare the polyesters.
  • suitable alcohols are trimethylolpropane, glycerol, erythritol, pentaerythritol, trimethylolbenzene or trishydroxyethyl isocyanurate.
  • dicarboxylic acids examples include phthalic acid, isophthalic acid, terephthalic acid, tetrahydrophthalic acid, hexahydrophthalic acid, cyclohexanedicarboxylic acid, adipic acid, azelaic acid, sebacic acid, glutaric acid, tetrachlorophthalic acid, maleic acid, fumaric acids, itaconic acid, malonic acid, suberic acid, 2-methylsuccinic acid, 3,3- Diethyl glutaric acid and 2,2-dimethyl succinic acid.
  • the possible anhydrides of these acids are also suitable.
  • the anhydrides are encompassed by the term "acid”.
  • monocarboxylic acids such as benzoic acid, hexanecarboxylic acid or fatty acids, provided that the average functionality of the polyol is greater than 2.
  • Saturated aliphatic or aromatic acids are preferred, such as adipic acid or isophthalic acid.
  • polycarboxylic acids such as trimellitic acid can be used.
  • hydroxycarboxylic acids that can be used as reactants in the preparation of a hydroxyl-terminated polyester polyol include hydroxycaproic acid, hydroxybutyric acid, hydroxydecanoic acid or hydroxy stearic acid.
  • suitable lactones include e-caprolactone or butyrolactone.
  • the suitable hydroxyl-containing polycarbonates are obtainable by reacting carbonic acid derivatives, for example diphenyl carbonate, dimethyl carbonate or phosgene with polyols.
  • carbonic acid derivatives for example diphenyl carbonate, dimethyl carbonate or phosgene
  • examples include ethylene glycol, 1,2- and 1,3-propanediol, 1,3- and 1,4-butanediol, 1,6-hexanediol, 1,8-octanediol, neopentylglycol, 1,4-bishydroxymethylcyclohexane, 2- Methyl-1, 3-propanediol, 2,2,4-trimethylpentane-l, 3-diol, dipropylene glycol, polypropylene glycols, dibutylene glycol, polybutylene glycols, bisphenol A, T etrabrombisphenol A, but also lactone-modified diols.
  • the diol component preferably contains 40 to 100% by weight of hexanediol, preferably 1,6-hexanediol and / or hexanediol derivatives, more preferably those which contain ether or ester groups in addition to terminal OH groups.
  • the polycarbonate polyols include branching through the incorporation of polyfunctional components, especially low molecular weight polyols.
  • Examples of compounds which are suitable for this purpose include glycerol, trimethylolpropane, hexane-l, 2,6-triol, butane-l, 2,4-triol, trimethylolpropane, pentaerythritol, quinitol, marinitol and sorbitol, methyl glycoside or 1, 3, 4, 6-dianhydrohexitol e.
  • the preparation of the polyacrylate copolymer can in principle be carried out by means of conventional free radical polymerization in organic phase.
  • the polyacrylate copolymer is preferably prepared in a multi-stage process, as already described in EP-A 0 947 557 or in EP-A 1 024 184.
  • a hydrophobic monomer mixture which is free of acid groups or with a low acid group content added, and then at a later time in the polymerization, a hydrophilic monomer mixture, containing acid groups, added, wherein the hydrophilic monomer mixture contains acid groups which are not monomers from Type (M4) and (M5) included.
  • the copolymerization is generally carried out at 40 to 180 ° C, preferably at 80 to 160 ° C.
  • Suitable initiators (I) for the polymerization reaction include organic peroxides such as di-tert-butyl peroxide, or tert-butyl peroxy-2-ethylhexanoate and azo compounds.
  • the amount of initiator used depends on the desired molecular weight. For reasons of operational safety and easier handling and peroxide initiators can be used in the form of a solution in suitable organic solvents of the type already mentioned.
  • the rate of addition of the initiator (I) in the process of the invention may be controlled to continue until the end of the monomer feed, and the amounts of solvent in steps one and two are chosen so that an organic solvent content of less than 20 wt .-% results.
  • the amounts of the ingredients are preferably calculated so as to give a mass ratio of (Ml): (M2) of 9: 1 to 6: 1, particularly preferably a mass ratio of (Ml): (M2) of 4: 1 to 3: 1.
  • (Ml) is also preferably: (M3) from 50: 1 to 40: 1, particularly preferably (Ml): (M3) from 35: 1 to 30: 1.
  • the radical polymerization can be carried out in the presence of a solvent or solvent / water mixture that is filled into the reaction vessel.
  • Suitable organic solvents are all known in Lackte chnologi e known solvents, with those are preferred, which are usually used as cosolvents in aqueous dispersions, such as alcohols, ethers, ethers containing ether groups, esters, ketones or nonpolar hydrocarbons or mixtures of these solvents ,
  • the Solvents are used in amounts such that their proportion in the finished dispersion is 0 to 20% by weight, preferably 0.1 to 15% by weight.
  • the number average molecular weight Mn of the polyacrylate copolymers can be set by a specific choice of the operating parameters, for example the molar monomer / initiator ratio, for example the reaction time or the temperature, generally between 500 g / mol and 30,000 g / mol, preferably between 1,000 g / mol and 15,000 g / mol, more preferably between 1,500 g / mol and 10,000 g / mol.
  • the hydroxyl group content of the polyacrylate copolymers in 100% form is preferably 1.5 to 12.0% by weight, preferably 2.0 to 10.0% by weight and more preferably 1.5 to 9.0% by weight
  • the acid groups present of the polyacrylate copolymers are preferably converted into their salt form by adding suitable neutralizing agents, at least proportionally.
  • suitable neutralizing agents are organic amines or water-soluble inorganic bases, such as, for example, soluble metal hydroxides, metal carbonates or metal hydrogencarbonates, for example sodium hydroxide or potassium hydroxide.
  • Suitable amines are butyldiethanolamine, N-methylmorpholine, triethylamine, ethyldiisopropylamine, N, N-dimethylethanolamine, N, N-dimethylisopropanolamine, N-methyldiethanolamine, diethylethanolamine, triethanolamine, butanolamine, morpholine, 2-aminomethyl-2-methylpropanol or isophoronediamine. In mixtures, it is also possible to use proportionate ammonia. Particularly preferred are triethanolamine, N, N-dimethylethanolamine and ethyldiisopropylamine.
  • the mixture of radically polymerizable monomers (M) does not contain: (M4) vinyl esters of aliphatic carboxylic acids.
  • vinyl esters of aliphatic carboxylic acids examples include the esterification products of vinyl alcohol with linear or branched, aliphatic carboxylic acids such as vinyl acetate, vinyl propionate, vinyl butyrate, vinyl 2-ethylhexanoate, vinyl octanoate, vinyl decanoate, vinyl neodecanoate, vinyl dodecanoate (vinyl laurate) or vinyl stearate.
  • the mixture of free-radically polymerizable monomers (M) does not contain: (M5): cycloaliphatic esters of (meth) acrylic acid and / or vinylaromatics.
  • these monomers to be avoided are cyclohexyl (meth) acrylate, alkyl group-substituted cyclohexyl (meth) acrylates, 4-tert-butylcyclohexyl (meth) acrylate, norbornyl (meth) acrylate, isobornyl (meth) acrylate, isobornyl acrylate and / or isobornyl methacrylate and / or mixtures of the above monomers.
  • the polyacrylate copolymer in 100% form has a hydroxyl group content of> 1.5 wt .-% to ⁇ 12.0 wt .-%, preferably from> 2.0 wt .-% to ⁇ 10.0 wt. -% on.
  • the hydroxyl group content can be calculated by dividing by 33 the hydroxyl number determined as described above.
  • the polyols (PO) have a hydroxyl group content of> 15 wt .-% to ⁇ 35 wt .-%, preferably from> 20 wt .-% to ⁇ 30 wt .-%, on.
  • Hydroxyl group content can be calculated by dividing the hydroxyl number determined by 33 as described above.
  • the polyols (PO) are polyester polyols obtained from the reaction of an at least tri-functional alcohol with a lactone.
  • a particularly preferred polyol is obtained from trimethylolpropane and e-caprolactone.
  • trimethylolpropane and e-caprolactone can be reacted in a weight ratio of> 60:40 to ⁇ 80:20, preferably> 68:32 to ⁇ 72:28.
  • the reaction may take place in the presence of a catalyst.
  • the monomers (III), (M2), (M3), (M4) and (M5) are used in the following amounts:
  • the polyurethane resin used according to the invention is preferably prepared by reacting a polyacrylate copolymer (B) with at least one uretdione group-containing hardener (A) based on aliphatic, (cyclo) aliphatic, araliphatic and / or aromatic polyisocyanates which does not have any chemically bonded hydrophilizing Contains groups homogeneously mixed in a non-aqueous system.
  • the carboxyl groups present in the polyacrylate copolymer (B) are preferably neutralized to at least 50%, more preferably 80% to 130%, particularly preferably 95 to 125% 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.
  • Amines such as e.g. Triethylamine, triethanolamine, diisopropylhexylamine, and dimethylethanolamine, particularly preferred are triethanolamine and 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, propyl englykolmono-n-butyleth er, 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. Examples:
  • Dowanol PnB Propylene glycol mono-n-butyl ether from Dow
  • Peroxan DB di-tert-butyl peroxide from Pergan.
  • Solvent Naphtha 100 an aromatic solvent, CAS: 64 742-95-6, from Azelis.
  • Veova 9 Versatic acid vinyl ester from the company Momentive. Used analytical methods:
  • 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 Malvem (DE) according to DIN ISO 13321: 2004-10.
  • the pH was determined using 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 gas chromatography with 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 chemical resistance was determined on a standardized coil test panel (Coil Coating black - CS 200570, Heinz Zanders für-Blech-Logiding).
  • a cotton swab soaked with the test substance xylene or water
  • IPDI isophorone diisocyanate
  • DMAP 4-dimethylaminopyridine
  • Part 1 of Table 1 was weighed into a stirring apparatus under nitrogen and heated to 138 ° C. Thereafter, Part 2 was added uniformly at 138 ° C in 20 min. Subsequently, immediately part 3 and part 4 were added in parallel in 4 hrs. 30 Min. At 138 ° C evenly. After the addition, the reaction mixture was kept at 138 ° C for 30 min. Finally, Part 5 and Part 6 were added uniformly in 1 hr. 30 Min. At 138 ° C in parallel. After the addition, the reaction mixture was further held at 138 ° C for 1 hr. After cooling, a slightly yellowish, highly viscous polyacrylate solution was obtained. 500 g of this solution were weighed into a stirring apparatus under nitrogen and heated to 70 ° C.
  • the dispersion remained stable at 23 ° C for 10 months.
  • Example 2 500 g polyacrylate solution from Example 1 were weighed into a stirring apparatus under nitrogen and heated to 70.degree. After homogenization, 283 g of the 60% crosslinker 1 solution in Dowanol PnB were added and the mixture was rehomogenized for 30 min. At 70 ° C, followed by addition of a mixture of 21.5 g triethanolamine and 4.3 g dimethylethanolamine. After stirring for a further 30 minutes at 70 ° C., 407 g of distilled water were stirred into the mixture. After fine adjustment of the viscosity to about 2000 mPas, a dispersion was obtained with the following characteristics:
  • Average particle size 175 nm
  • the dispersion remained stable at 23 ° C for 10 months.
  • Part 1 of Table 2 was weighed into a stirring apparatus under nitrogen and heated to 138 ° C. Thereafter, Part 2 was added uniformly at 138 ° C in 20 min. Subsequently, immediately part 3 and part 4 were added in parallel in 4 hrs. 30 Min. At 138 ° C evenly. After the addition, the reaction mixture was kept at 138 ° C for 30 min. Finally, Part 5 and Part 6 were added uniformly in 1 hr. 30 Min. At 138 ° C in parallel. After the addition, the reaction mixture was further held at 138 ° C for 1 hr. After cooling to give a slightly yellowish, highly viscous polyacrylate solution at 100 ° C, the reaction mixture was bottled.
  • the dispersion remained stable for 5 months at 23 ° C.
  • Part 1 from Table 3 was weighed into a stationary apparatus under nitrogen and heated to 148 ° C. Thereafter, Part 2 was uniformly added at 148 ° C in 20 min. Subsequently, Part 3 and Part 4 were added in parallel at the same time in 6 hours at 148 ° C. After the addition, the reaction mixture was held at 148 ° C for 60 min. After cooling to 80 ° C, the polyacrylate solution was bottled. Table 4
  • Part 1 of Table 4 was weighed into a stirring apparatus under nitrogen and heated to 144 ° C. Thereafter, part 2 was uniformly added at 144 ° C in 20 min. Subsequently, Part 3 and Part 4 were immediately added in parallel in 4 hrs. 30 Min. At 144 ° C evenly. After the addition, the reaction mixture was held at 144 ° C for 5 min. Finally, Part 5 and Part 6 were added uniformly in 1 hour 30 min. At 144 ° C dosed. After the addition, the reaction mixture was again held at 144 ° C for 1 hr. After cooling, a slightly yellowish, highly viscous polyacrylate solution was obtained.
  • the dispersion remained stable for 5 months at 23 ° C.
  • the dispersions were homogenized in a speed mixer at 2000 rpm for 1 minute on a coil plate with a doctor blade with a layer thickness of 180 mih (wet).
  • the plates with the applied wet paints were baked for 5 min at room temperature, for 30 min at 180 ° C and then stored for 24 hours at room temperature.
  • the stored films were evaluated by application technology (Table 6).
  • the uretdione-containing dispersions according to the invention give hard and stable coatings. From the uretdione-containing dispersions according to the invention, it is possible to produce both glossy and semi-gloss coatings h.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Sealing Material Composition (AREA)
  • Paints Or Removers (AREA)
  • Application Of Or Painting With Fluid Materials (AREA)

Abstract

La présente invention concerne des compositions aqueuses contenant des groupes uretdione, comprenant ou constituées par (A) au moins un durcisseur contenant des groupes uretdione, à base de polyisocyanates aliphatiques, cycloaliphatiques, araliphatiques et/ou aromatiques, qui ne contient pas de groupes d'hydrophilisation liés chimiquement ; (B) au moins un copolymère de polyacrylate ; (C) le cas échéant des solvants ; et (D) le cas échéant des adjuvants et des additifs ; le rapport des quantités des composants (A) et (B) étant dimensionné de manière telle que le rapport molaire des groupes NCO se trouvant sous forme d'uretdione du durcisseur (A) aux groupes réactifs avec NCO du copolymère de polyacrylate (B) vaut 3:0,5 à 0,5:3 et A et B se trouvant sous forme de mélange physique. En outre, l'invention concerne un procédé pour la préparation d'une couche de polyuréthane à l'aide de la composition aqueuse contenant des groupes uretdione de la présente invention, la couche de polyuréthane ainsi obtenue et un substrat qui est revêtu ou collé à l'aide de cette couche de polyuréthane.
EP19711129.7A 2018-03-23 2019-03-21 Compositions aqueuses contenant des groupes uretdione et procédé pour leur préparation Pending EP3768751A1 (fr)

Applications Claiming Priority (16)

Application Number Priority Date Filing Date Title
US15/933,527 US20190292296A1 (en) 2018-03-23 2018-03-23 Polyol acid neutralization for low temperature uretdione curing
US15/933,475 US11008416B2 (en) 2018-03-23 2018-03-23 Aqueous, curable composition, comprising dispersed uretdione prepolymer, reactant and azolate
EP18163620.0A EP3543269A1 (fr) 2018-03-23 2018-03-23 Dispersions de polyuréthane contenant de l'uretdione comprenant des groupes hydrophiles
US15/933,570 US10731051B2 (en) 2018-03-23 2018-03-23 Basecoat acid neutralization through inorganic salts
US15/933,507 US20190292294A1 (en) 2018-03-23 2018-03-23 One component allophanate formulations through basecoat catalyst migration
EP18163621.8A EP3543270A1 (fr) 2018-03-23 2018-03-23 Système catalyseur pour dispersions d'uretdions
US15/933,495 US11312881B2 (en) 2018-03-23 2018-03-23 One component polyurethane/allophanate formulations with reactive reducer
US15/933,500 US10696775B2 (en) 2018-03-23 2018-03-23 Curing for polyallophanate compositions through undercoat acid neutralization
EP18163625.9A EP3543271A1 (fr) 2018-03-23 2018-03-23 Compositions aqueuses contenant des groupes urétdione et son procede de fabrication
US15/933,511 US11440988B2 (en) 2018-03-23 2018-03-23 Polyuretdione-containing resin blend compositions
US15/933,470 US11292864B2 (en) 2018-03-23 2018-03-23 Compositions using polyuretdione resins
US15/933,487 US20190292305A1 (en) 2018-03-23 2018-03-23 Uretdione based polyurethane compositions
US15/933,553 US10633477B2 (en) 2018-03-23 2018-03-23 Extended pot-life for low temperature curing polyuretdione resins
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/EP2019/057069 WO2019180131A1 (fr) 2018-03-23 2019-03-21 Compositions aqueuses contenant des groupes uretdione et procédé pour leur préparation

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EP3768751A1 true EP3768751A1 (fr) 2021-01-27

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EP19713668.2A Pending EP3768756A1 (fr) 2018-03-23 2019-03-21 Neutralisation d'acide polyol pour durcissement d'urétdione à basse température
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
EP19711125.5A Pending EP3768749A1 (fr) 2018-03-23 2019-03-21 Compositions aqueuses contenant des groupes uretdione et leur procédé de préparation
EP19713670.8A Withdrawn EP3768758A1 (fr) 2018-03-23 2019-03-21 Formulations de polyuréthane/allophanate à un seul composant comprenant un réducteur réactif
EP19713667.4A Withdrawn EP3768755A1 (fr) 2018-03-23 2019-03-21 Compositions utilisant des résines polyurétdione
EP19711128.9A Withdrawn EP3768745A1 (fr) 2018-03-23 2019-03-21 Dispersions de polyuréthane contenant de l'urétdione comprenant des groupes hydrophiles
EP19713339.0A Pending EP3768752A1 (fr) 2018-03-23 2019-03-21 Neutralisation d'acide de couche de fond au moyen de sels inorganiques
EP19711127.1A Withdrawn EP3768748A1 (fr) 2018-03-23 2019-03-21 Système catalytique pour dispersions d'uretdione
EP19713666.6A Withdrawn EP3768754A1 (fr) 2018-03-23 2019-03-21 Compositions de mélange de résines contenant des polyuretdione
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
EP19711126.3A Pending EP3768750A1 (fr) 2018-03-23 2019-03-21 Compositions aqueuses contenant des groupes uretdione et leur procédé de préparation
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

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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
EP19711125.5A Pending EP3768749A1 (fr) 2018-03-23 2019-03-21 Compositions aqueuses contenant des groupes uretdione et leur procédé de préparation
EP19713670.8A Withdrawn EP3768758A1 (fr) 2018-03-23 2019-03-21 Formulations de polyuréthane/allophanate à un seul composant comprenant un réducteur réactif
EP19713667.4A Withdrawn EP3768755A1 (fr) 2018-03-23 2019-03-21 Compositions utilisant des résines polyurétdione
EP19711128.9A Withdrawn EP3768745A1 (fr) 2018-03-23 2019-03-21 Dispersions de polyuréthane contenant de l'urétdione comprenant des groupes hydrophiles
EP19713339.0A Pending EP3768752A1 (fr) 2018-03-23 2019-03-21 Neutralisation d'acide de couche de fond au moyen de sels inorganiques
EP19711127.1A Withdrawn EP3768748A1 (fr) 2018-03-23 2019-03-21 Système catalytique pour dispersions d'uretdione
EP19713666.6A Withdrawn EP3768754A1 (fr) 2018-03-23 2019-03-21 Compositions de mélange de résines contenant des polyuretdione
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
EP19711126.3A Pending EP3768750A1 (fr) 2018-03-23 2019-03-21 Compositions aqueuses contenant des groupes uretdione et leur procédé de préparation
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

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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

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CN111886272A (zh) 2020-11-03
EP3768752A1 (fr) 2021-01-27
WO2019180130A1 (fr) 2019-09-26
EP3768745A1 (fr) 2021-01-27
WO2019183305A1 (fr) 2019-09-26
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CN111886272B (zh) 2022-11-15
EP3768750A1 (fr) 2021-01-27
CN111886273A (zh) 2020-11-03
CN112105666A (zh) 2020-12-18
WO2019183300A1 (fr) 2019-09-26
CN111868133A (zh) 2020-10-30
EP3768749A1 (fr) 2021-01-27
CN111886271A (zh) 2020-11-03
EP3768754A1 (fr) 2021-01-27
CN112041367A (zh) 2020-12-04
EP3768757A1 (fr) 2021-01-27
WO2019183307A1 (fr) 2019-09-26
CN112105666B (zh) 2023-05-23
WO2019180128A1 (fr) 2019-09-26
WO2019180131A1 (fr) 2019-09-26
EP3768759A1 (fr) 2021-01-27
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EP3768747A1 (fr) 2021-01-27
CN112105665A (zh) 2020-12-18
EP3768755A1 (fr) 2021-01-27
EP3768748A1 (fr) 2021-01-27
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