EP3768748A1 - Système catalytique pour dispersions d'uretdione - Google Patents

Système catalytique pour dispersions d'uretdione

Info

Publication number
EP3768748A1
EP3768748A1 EP19711127.1A EP19711127A EP3768748A1 EP 3768748 A1 EP3768748 A1 EP 3768748A1 EP 19711127 A EP19711127 A EP 19711127A EP 3768748 A1 EP3768748 A1 EP 3768748A1
Authority
EP
European Patent Office
Prior art keywords
acid
uretdione
catalyst system
group
catalyst
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.)
Withdrawn
Application number
EP19711127.1A
Other languages
German (de)
English (en)
Inventor
Saskia BEUCK
Sebastian Dörr
Hans-Josef Laas
Dorota Greszta-Franz
Nusret Yuva
Ralph-Georg BORN
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 Deutschland AG
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 EP18163620.0A external-priority patent/EP3543269A1/fr
Priority claimed from US15/933,495 external-priority patent/US11312881B2/en
Priority claimed from US15/933,570 external-priority patent/US10731051B2/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 US15/933,487 external-priority patent/US20190292305A1/en
Priority claimed from US15/933,511 external-priority patent/US11440988B2/en
Priority claimed from EP18163621.8A external-priority patent/EP3543270A1/fr
Priority claimed from US15/933,507 external-priority patent/US20190292294A1/en
Priority claimed from US15/933,475 external-priority patent/US11008416B2/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 EP18163625.9A external-priority patent/EP3543271A1/fr
Priority claimed from EP18181876.6A external-priority patent/EP3590987A1/fr
Priority claimed from EP18181877.4A external-priority patent/EP3590988A1/fr
Application filed by Covestro Deutschland AG, Covestro LLC filed Critical Covestro Deutschland AG
Publication of EP3768748A1 publication Critical patent/EP3768748A1/fr
Withdrawn 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 a catalyst system comprising
  • the present invention further relates to a kit, which comprises the catalyst system of the present invention and an aqueous uretdione dispersion having an acid value of from 1 to 100 mg KOH / g and further having at least one carboxyl group, a process for producing a polyurethane layer comprising the catalyst system of the present invention and said uretdione dispersion and the thereby obtained Polyurethane layer, as well as the use of the catalyst system for curing aqueous uretdione dispersions and / or for the production of paints or coatings.
  • EP 0 803 524 A1 describes amidines as catalysts in uretdione group-containing PU powder coating compositions.
  • the uretdione component and the OH-containing binder component are solid at room temperature. These are applied to the substrate by electrostatic powder spraying or vortex sintering, the curing temperatures being above 130 ° C. Their application as aqueous systems is not possible.
  • EP1526146 A1 describes a polyurethane powder coating composition.
  • the activity of the amidine catalysts decreases significantly in the presence of acids.
  • Epoxide group-terminated, uretdione-group-containing polyaddition compounds having a melting point of 40-130 ° C. are used.
  • the epoxide is anchored in the backbone, it is for example 2,3-epoxy-l-propanol and / or epoxidized soybean oil used.
  • a catalyst from the group of metal acetylacetonates, metal hydroxides, metal alcoholates, quaternary ammonium hydroxides, quaternary ammonium fluorides or quaternary ammonium carboxylates is used for curing.
  • the curing temperature is usually 120-160 ° C. Their application as aqueous systems is not possible.
  • WO 2009/095117 Al powder coating compositions which have a melting point of more than 40 ° C.
  • the catalyst used are quaternary ammonium salts or phosphonium salts.
  • the co-catalyst used is an epoxide compound of terephthalic acid diglycidyl ether and trimellitic triglycidyl ether (Araldit PT 912) or acetylacetonate. With these systems, no curing temperatures below 120 ° C are possible. Also, their use as aqueous systems is not possible.
  • the object of the present invention was therefore to develop catalyst systems for the crosslinking of aqueous anionic polyurethane dispersions containing uretdione groups.
  • a cross-linking of the polymers should be possible.
  • the polymerization should preferably be able to take place below 100 ° C. (low-temperature crosslinking).
  • the catalyst systems should also be insensitive to acidic conditions.
  • the catalyst systems should contain no organometallic compounds.
  • a catalyst system comprising or consisting of
  • the present invention relates to:
  • Catalyst system comprising or consisting of
  • Catalyst system according to embodiment 1 or 2 characterized in that the at least one acid scavenger B) is selected from aliphatic or aromatic alcohols, diols, polyols, ethers and acids containing at least one epoxy group.
  • Catalyst system characterized in that A) to B) in a mass ratio of 1: 1 to 10: 1, preferably 2: 1 to 6: 1 and / or A) to C) in a mass ratio of 0.5: 1 to 5: 1, preferably 1: 1 to 2: 1 and / or B) to C) in a mass ratio of 1: 1 to 1:10, preferably 1: 1 to 1: 6 present.
  • a kit comprising the catalyst system according to any of embodiments 1 to 5 and separately therefrom an aqueous uretdione dispersion characterized by having an acid value of 1 to 100 mg KOH / g, preferably 2 to 50 mg KOH / g, stronger 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 of 2: 1 as a solvent and also having at least one carboxyl group.
  • kits according to embodiment 6 characterized in that the equivalent ratio of uretdione to hydroxy groups used is 0.5: 1 to 1: 0.5, preferably 0.75: 1 to 1: 0.75, most preferably 1: 1 ,
  • a process for producing a polyurethane layer comprising the steps
  • aqueous Uretdiondispersion having 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 the weight ratio 2: 1 as a solvent, and having at least one carboxyl group;
  • step iv) drying the mixture from step iii), preferably at room temperature and v) curing the mixture from step iv) with heat to 120 ° C, preferably up to 100 ° C, for up to 180 minutes, preferably up to 120 minutes.
  • molecular weights are determined by GPC (gel permeation chromatography) using polystyrene standards.
  • percentages by weight in the present invention refer to the total weight of the particular system or the total weight of the particular component.
  • a copolymer may contain a given monomer in weight percent, in which case the weight percentages would be based on the total weight of the copolymer.
  • At least one refers to the nature of the compounds rather than individual molecules.
  • at least one acid scavenger B is to be understood as containing at least one type of acid scavenger, but contained in an arbitrary number of molecules in the composition.
  • two or more types of acid scavengers may be present in any arbitrary number, if the amounts are not defined.
  • a kit in the sense of the present invention is a system in which the catalyst system of the present invention and the aqueous carboxyl group-containing uretdione dispersion are spatially separated from each other.
  • the catalyst system comprises at least one compound A) selected from azoles, oxazoles, thiazoles, benzotriazole, benzimidazole, and benzoxazole and their salts.
  • the at least one compound A) is selected from pyrazole, imidazole, 1,2,3-triazole, 1,2,4-triazole and benzotriazole and their salts.
  • the salts are preferably alkali metal, alkaline earth metal or ammonium salts.
  • the at least one compound A) selected from 1,2,3-triazole, 1,2,4-triazole and benzotriazole and their salts, more preferably from the alkali and alkaline earth salts of 1,2,3-triazole, 1 2,4-triazole and benzotriazole; most preferably from the Na, Li and K salts of 1,2,3-triazole, 1,2,4-triazole and benzotriazole, especially the sodium salts thereof.
  • the catalyst system comprises at least one acid scavenger B) containing at least one epoxy group.
  • the at least one acid scavenger B) is selected from aliphatic or aromatic alcohols, diols, polyols, ethers and acids containing at least one epoxy group, preferably selected from C 2-20 alcohols, C 2-20 diols, C 4- 50 polyols having at least 3 hydroxy groups, C 3-50 ethers and polyethers and C 3-20 acids containing at least one epoxy group.
  • glycidyl ethers such as butyl glycidyl ether, pentaerythritol tetraglycidyl ether, glycidyl isopropyl ether, 2-ethylhexyl glycidyl ether,
  • Polyethylene glycol diglycidyl ether, 1,4-cyclohexanedimethanol diglycidyl ether or polyfunctional glycidyl ethers which are commercially available under the name HELOXY TM Modifier from Hexion.
  • the at least one acid scavenger B) preferably has a viscosity of from 5 to 500 mPas, more preferably from 50 to 250 mPas, most preferably from 100 to 200 mPas, measured at 25 ° C. according to DIN 53015: 2001-02.
  • the at least one acid scavenger B) has an epoxy equivalent (weight per epoxy group) of 120 to 650 g / eq, preferably 125 to 250 g / eq, measured according to DIN 16945: 1989-03.
  • the at least one acid scavenger B) has an epoxy value of from 20.0 to 35.0%, more preferably from 23.5 to 33.0%, most preferably from 26.5 to 32.5%, measured according to DIN 16945: 1989-03.
  • Suitable amidine catalysts C) in which the CN double bond is present as part of an open-chain molecule are, for example, N, N-dimethyl-N'-phenylformamidine or N, N, N'-trimethylformamidine, the preparation of which, for. In Chem. Ber. 98, 1078 (1965).
  • suitable amidines C) in which the CN double bond is part of a cyclic system may be mentioned here: in 1-position substituted 2-methyltetrahydropyrimidines, as described for.
  • Suitable catalysts C) in which the CN double bond is arranged exocyclically on a ring system are, for example, imines of N-alkyl-substituted lactams, such as 2-methylimino-1-methylpyrrolidone, the preparation of which, for. In Chem. Ber. 101, 3002 (1968).
  • Preferred as at least one component C) are bicyclic, N, N, N'-trisubstituted amidine-containing catalysts of the general formula (1)
  • n is an integer from 1 to 3, preferably 2.
  • Such bicyclic amidines is known and described, for example, in DE 1 545 855 A1 or EP 662 476 A1.
  • Particularly preferred catalysts C) are 1,5-diazabicyclo [4.3.0] non-5-ene (DBN) and 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU), in particular DBU.
  • the invention further relates to a kit in which an acidic aqueous uretdione dispersion and the catalyst system of the present invention are present separately.
  • Suitable uretdione dispersions are those generally known to those skilled in the art, with the proviso that they have 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 the weight ratio 2: 1 as solvent, and having at least one carboxyl group.
  • a first step (I) an ionic uretdione group-containing, hydrophilicized, hydroxyl or isocyanate end-group-containing prepolymer by reaction of
  • BG further polyol component
  • M n molecular weight of 62 to 500 g / mol, preferably 62 to 400 g / mol, particularly preferably 62 to 300 g / mol
  • AG polyisocyanates
  • polyisocyanates (AG) having an NCO functionality of> 2 and
  • the implementation of the first two synthesis steps can be carried out in the reverse order or in a single reaction step. It is also possible to use the polyol component (BG) proportionally in the preparation of the prepolymer (I). It is likewise possible to use the compound (C) proportionally in the prepolymerization (II) of the uretdione group-containing polyisocyanate mixture.
  • an acid-functional compound (C) and a further polyisocyanate component (AG) are added simultaneously or in a further step.
  • Suitable polyisocyanate components are aliphatic, cycloaliphatic, araliphatic and / or aromatic isocyanates having an average functionality of from 2 to 5, preferably 2 and having an isocyanate content of from 0.5 to 60% by weight, preferably from 3 to 40% by weight.
  • % particularly preferably from 5 to 30 wt .-%, such as 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, Toluylene diisocyanate (TDI), diphenylmethane-2,4'- and / or 4,4'-diisocyanate (MDI), triphenylmethane-4,4'-diisocyanate or naphthylene-l, 5-diiso
  • isophorone diisocyanate dicyclohexylmethane 2,4'- and / or 4,4'-diisocyanate or hexamethylene diisocyanate, in particular isophorone diisocyanate.
  • Suitable polyisocyanates are also the known prepolymers having terminal isocyanate groups, such as are obtainable in particular by reacting the abovementioned simple polyisocyanates, especially diisocyanates, with substoichiometric amounts of organic compounds having at least two isocyanate-reactive functional groups.
  • the ratio of isocyanate groups to NCO-reactive hydrogen atoms is 1.05: 1 to 10: 1, preferably 1.5: 1 to 4: 1, wherein the hydrogen atoms are preferably derived from hydroxyl groups.
  • the type and proportions of the starting materials used in the preparation of NCO prepolymers are selected so that the NCO prepolymers preferably have an average NCO functionality of 2 to 3 and a number average molecular weight of 300 to 10,000 g / mol, preferably 800 to 4000 g / mol.
  • Suitable components (A2 ') are polyisocyanates which contain 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. 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 from which the uretdione-containing building blocks (A2 ') are synthesized are tetramethylene diisocyanate, cyclohexane-1,3- and 1,4-diisocyanate, pentamethylene diisocyanate, hexamethylene diisocyanate (HDI), 1-isocyanato-3,3, 5-trimethyl-5-isocyanatomethylcyclohexane (isophorone diisocyanate IPDI), dicyclohexylmethane 2,4'- and / or 4,4'-diisocyanate, tetramethylxylylene diisocyanate (TMXDI), triisocyanatononane,
  • Toluylene 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 isocyanates.
  • TDI Toluylene diisocyanate
  • MDI diphenylmethane-2,4'- and / or 4,4'-diisocyanate
  • triphenylmethane-4,4'-diisocyanate or naphthylene-l 5-diisocyanate and any mixtures of such isocyanates.
  • isophorone diisocyanate dicyclohexylmethane 2,4'- and / or 4,4'-diisocyanate or hexamethylene diisocyanate.
  • component (A2 ') may also have isocyanurate, biuret, allophanate, urethane and / or urea structures.
  • the polyol component (BG) 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 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 acid functional compounds (C) are hydroxy-functional carboxylic acids, preferably mono- and dihydroxycarboxylic acids, e.g. 2-hydroxyacetic acid, 3-hydroxypropanoic acid or 12-hydroxy-9-octadecanoic acid (ricinoleic acid).
  • Preferred carboxylic acids (C) are those in which the carboxyl group is hindered in its reactivity due to steric effects, e.g. Lactic acid.
  • Particularly preferred are 3-hydroxy-2,2-dimethylolpropanoic acid (hydroxypivalic acid) or dimethylolpropionic acid, most preferably exclusively dimethylolpropionic acid is used.
  • step (I) if component (BG) is used as a proportion in step (I), its proportion is at most 50% by weight, based on the sum of components (C) and (BG). Preferably, in step (I) only component (C) is used.
  • the polyol component (B2 ') is selected from the group of
  • linear, difunctional polyols having average molecular weights Mn of from 350 to 4000 g / mol, preferably from 350 to 2000 g / mol, particularly preferably from 350 to 1000 g / mol,
  • Suitable polyol component (bl) are 2 to 6-hydric alcohols and / or mixtures thereof which have no ester groups. Typical examples are 1,2-ethanediol, 1,2-propanediol and 1,3-diol, 1,4-butanediol, 1,2 or 2,3, 1,6-hexanediol, 1,4-dihydroxycyclohexane, glycerol, Trimethylolethane, trimethylolpropane, pentaerythritol and sorbitol. Of course, as component (bl) it is also possible to use alcohols with ionic groups or groups convertible into ionic groups. Preference is given, for example, to 1,4- or 1,3-butanediol, 1,6-hexanediol or trimethylolpropane and mixtures thereof.
  • Suitable linear difunctional polyols (b2) are selected from the group of polyethers, polyesters and / or polycarbonates.
  • the polyol component (b2) contains at least one ester group-containing diol of molecular weight Mn from 350 to 4000 g / mol, preferably from 350 to 2000 g / mol, more preferably from 350 to 1000 g / mol. It is the average, calculated from the hydroxyl number molecular weight.
  • the ester diols are mixtures in which, in minor amounts, individual components 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.
  • component (b2) are polycaprolactone diols having an average molecular weight of from 350 to 4000 g / mol, preferably from 350 to 2000 g / mol, particularly preferably from 350 to 1000 g / mol, which are prepared in a manner known per se from a diol or diol mixture the type exemplified above as starter and e-caprolactone have been prepared.
  • the preferred starter molecule is 1,6-hexanediol.
  • Particularly preferred are those polycaprolactone diols which have been prepared by polymerization of e-caprolactone using 1,6-hexanediol as a starter.
  • linear polyol component (b2) it is also possible to use (co) polyethers of ethylene oxide, propylene oxide and / or tetrahydrofuran.
  • polyethers having an average molecular weight Mn of from 500 to 2000 g / mol, such as e.g. Polyethylene 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.
  • Suitable mono-functional linear polyethers (b3) are, for example, (co) polyethers of ethylene oxide and / or propylene oxide. Preference is given to monoalcohol-initiated polyalkylene oxide polyethers of average molecular weight Mn of from 350 to 2500 g / mol with at least 70% of ethylene oxide units.
  • (co) polymers with more than 75% ethylene oxide units and a molecular weight Mn of 350 to 2500 g / mol, preferably from 500 to 1000 g / mol.
  • As starter molecules in the preparation of these polyether monofunctional alcohols having 1 to 6 carbon atoms are preferably used.
  • Suitable polyols (B3 ') are polyols having an OH functionality greater than or equal to 2, and with average molecular weights of 500 to 5000 g / mol, preferably from 500 to 3000 g / mol, particularly preferably from 500 to 2000 g / mol.
  • Preferred polyols (B3 ') are e.g. Polyether average molecular weight of 300 to 2000 g / mol and an average functionality of 2.5 to 4 OH groups / molecule. Also preferred are polyesters of average OH functionality of 2.5 to 4.0. Suitable diols and dicarboxylic acids for the polyesters are those mentioned under component (b2), but additionally contain tri- to hexafunctional short-chain polyols, e.g. Trimethylolpropane, pentaerythritol or sorbitol.
  • polyester polyols based on adipic acid, phthalic acid, isophthalic acid and tetrahydrophthalic acid, as well as 1,4-butanediol and 1,6-hexanediol.
  • the carboxylic acid groups present in the polyurethanes of the invention are preferably at least 50%, more preferably 80% to 120%, particularly preferably 95 to 105% neutralized with suitable neutralizing agents (N) and then dispersed with deionized water.
  • the neutralization can take place before, during or after the dispersing or dissolving step. However, preference is given to neutralization before the addition of water.
  • Amines such as e.g. Triethylamine, diisopropylhexylamine, particularly preferred is dimethylethanolamine.
  • suitable uretdione dispersions of the present invention are storage-stable, reactive aqueous uretdione-group-containing compositions which comprise a physical mixture dispersed in water and, if appropriate, organic solvents
  • (B12) at least one hydroxyl-containing polyol which contains at least one chemically bonded carboxylic acid group
  • the amount ratio of the components (Al l) and (Bl 2) is such that the molar ratio of the uretdione present NCO groups of the harder (Al l) to NCO-reactive groups of the polyol (B12) 0.5: 1 to 1: 0.5 and 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 of 2: 1 as a solvent.
  • Suitable polyisocyanates containing uretdione groups as starting compounds for the component (Al 1) are the polyisocyanates (A2 ') described above.
  • reaction of these uretdione group-carrying polyisocyanates to uretdione-containing hard (Al1) involves the reaction of the free NCO groups of the starting compounds (A2 ') with the polyol component (BG), optionally with the concomitant use of the polyol component (b2).
  • polyol component in the preparation of uretdione groups having curing agent (Al l) also low molecular weight ester-containing 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.
  • ester-containing diols or mixtures of such diols are, for. B. by reacting alcohols with minor amounts of dicarboxylic acids, corresponding dicarboxylic anhydrides, corresponding dicarboxylic acid esters of lower alcohols or lactones.
  • suitable acids are succinic acid, adipic acid, sebacic acid, phthalic acid, isophthalic acid, phthalic anhydride, tetrahydrophthalic acid, maleic acid, maleic anhydride, terephthalic acid dimethyl ester and terephthalic acid bis-glycol ester.
  • Suitable lactones for the preparation of 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.
  • solvents may be used in the preparation of the uretdione group-containing hardeners (Al 1).
  • Suitable solvents for uretdione hardeners (Al l) are all liquid substances which do not react with other ingredients, eg. As acetone, methyl ethyl ketone, ethyl acetate, butyl acetate, xylene, Solvesso 100, Solvesso 150, propylene glycol mono-n-butyl ether (Dowanol PnB, (Dow Chemicals)), ® Proglyde DMM (Dow Chemicals), methoxypropyl acetate and Dibasicester.
  • the uretdione group-containing hardener (Al l) are free from ionic or non-ionic hydrophilizing compounds.
  • ionically hydrophilizing compounds the person skilled in the art understands compounds which have at least one group capable of 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 hardening agents (Al 1) are preferably free of anion-forming, 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 uretdione hardening agents (Al 1) 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 (Al 1) are furthermore preferably free from nonionically hydrophilizing compounds, such as, for example, polyalkylene oxide polyether alcohols or polyalkylene oxide polyether amines.
  • the uretdione groups are hardeners (Al 1) preferably free of polyethylene oxide polyether or mixed polyalkylene oxide polyethers whose alkylene oxide units consist of at least 30 mol% of ethylene oxide units.
  • Suitable polyols (Bl 2) can be selected from polyester polyols, polyether polyols, polyurethane ether polyols, polyurethane ester polyols, polycaprolactone polyols,
  • Starting component for the polyols (B12) are those polyols, preferably diols, in question, which contain at least one carboxylic acid group, generally 1 to 3 carboxylic acid groups per molecule.
  • dihydroxycarboxylic acids such as a, a-dialkylolalkanoic acids, especially a, a dimethylolalkanoic acids, such as 2,2-dimethylolacetic acid, 2,2-
  • Suitable polyols (B12) are polyols having an OH content greater than 1% by weight (calculated as OH group on solid content, molecular weight 17 g / mol) and with number-average molecular weights Mn from 500 to 20,000 g / mol, preferably from 500 to 10,000 g / mol, more preferably from 500 to 5,000 g / mol.
  • Suitable neutralizing agents (N) 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.
  • solvents under (CI 3) are all liquid substances suitable that do not react with other ingredients. Preferred are acetone, methyl ethyl ketone, ethyl acetate, butyl acetate, xylene, Solvesso 100, Solvesso 150, propylene glycol mono-n-butyl ether (Dowanol PnB), methoxypropyl acetate and dibasic ester.
  • the solvent used can then be removed by distillation.
  • leveling agents such as polysilicones or acrylates, light stabilizers, for.
  • sterically hindered amines, or other auxiliaries such as.
  • fillers and pigments such as titanium dioxide may be added in an amount of up to 50% by weight of the uretdione dispersion. Examples:
  • the uretdione ring opening was characterized by a Bruker FT-fR spectrometer (Tensor II with platinum ATR (diamond crystal) unit) The spectra were recorded in a wavenumber range of (4000-400) cm 1. The maximum of the uretdione peak (approximately 1760 cm 1 ) was evaluated, and peak heights to comparative systems were compared to an initial value set to 100% (uretdione film without catalyst, dried at room temperature) The uretdione peak height of the films cured at 180 ° C. for 30 min set to 0%. Variations were determined relative to these 100 and 0% values (ratio formation).
  • the solids content (non-volatile content) was determined by heating a weighed sample at 125 ° C to constant weight. At constant weight, the solids content is calculated by weighing the sample back.
  • the NCO content was determined volumetrically according to DIN-EN ISO 11909.
  • the control of free NCO groups was carried out by IR spectroscopy (band at 2260 cm 1 ).
  • the indicated viscosities were determined by means of rotational viscometry according to DIN 53019: 2016-10 at 23 ° C. using a rotational viscometer with a shear rate of 40 l / s, Anton Paar Germany GmbH, Ostfildern, Germany.
  • the mean particle sizes (number average) of the polyurethane dispersions were determined after dilution with deionized water by laser correlation spectroscopy (instrument: Malvern Zetasizer 1000, Malver Inst. Limited, London, UK).
  • the zeta potential was measured by diluting one drop of the sample with 20 mL of demineralized water and homogenizing by stirring. Subsequently, the zeta potential was determined at 23 ° C in the Malvern Nanosizer ZS90 (Malvern Instruments,dorfberg, Germany).
  • the acid number of the respective dispersion was determined in accordance with DIN EN ISO 2114: 2002-06.
  • the solvent used was a mixture of acetone and ethanol (2: 1, by weight).
  • the unit of acid number is mg KOH per g of the sample analyzed.
  • Heloxy Modifier TP Polyfunctional glycidyl ether of trimethylolpropane, Hexion
  • Bayhydrol A2695 water-dilutable, OH-functional polyacrylate dispersion; about 41% in water / l-butoxy-2-propanol, neutralized with triethanolamine / dimethylethanolamine, 7.2% 1-butoxy-2-propanol, Fa. Covestro
  • Dowanol PnB Propylene glycol mono-n-butyl ether, Dow
  • Solvent Naphtha 100 an aromatic solvent, Azelis
  • DMPS Dimethylolpropionic acid
  • IPDI isophorone diisocyanate
  • DMAP 4-dimethylaminopyridine
  • the resulting white dispersion had the following properties:
  • 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 again held at 138 ° C for 1 hr. After cooling to 100 ° C, the reaction mixture was bottled. This gave a slightly yellowish, highly viscous polyacrylate solution.
  • 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 again held at 138 ° C for 1 hr. After cooling to 110 ° C, the reaction mixture was bottled. This gave a slightly yellowish, highly viscous polyacrylate solution.
  • Part 1 from Table 3 was weighed into a stirring apparatus under nitrogen and heated to 148 ° C. Thereafter, Part 2 was uniformly added at 128 ° 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 the addition, the reaction mixture was again held at 148 ° C for 1 hr. After cooling to 80 ° C, the polyacrylate solution was bottled.
  • the uretdione dispersion of Preparation Example 1 was dispersed in water and then mixed in a speed mixer (2000 rpm) with Bayhydrol A2695. Heloxy Modifier TP was added, then 1,2,4-Na triazolate (10% in water) and DBU (10% in water, freshly mixed) were added. The mixture was again mixed with a speed mixer (2000 rpm) and allowed to stand on the bench for 30 minutes for foam reduction.
  • the mixture was applied to glass or sheet with a coating knife having a layer thickness of 150-180 ⁇ m (wet).
  • the plates were dried at room temperature for 5 minutes and then baked at 100 ° C for 30 minutes.
  • the resulting coatings were evaluated by application technology and an IR spectrum was recorded.
  • the uretdione dispersion from Preparation Examples 3 ad was in a speed mixer (2000 rev / min) with the uretdione dispersion of Preparation Example 1, Heloxy Modifier TP, 1,2,4-Na triazolate (10% in water) and DBU (10% in water, freshly mixed). The mixture was allowed to stand for 30 minutes to reduce foam.
  • the curing reaction can be monitored by observing the ring opening of the uretdione by IR spectroscopy.
  • IR uretdione peak With the combination of sodium triazolate, DBU and heloxy modifier TP, the IR uretdione peak has almost disappeared ( ⁇ 4% relative to the height of the uretdione peak of the dried starting material).
  • Pendulum hardness also increases with the effectiveness of the catalyst mixture.
  • the resistance to xylene, MPA, EA and acetone should be at least 1/1/2/4, the water resistance must be at least 1-2. Both resistances can only be obtained by the catalyst mixture.
  • an equimolar amount of uretdione to alcohol (entries 13 to 16) leads to much higher hardnesses and better resistances than an excess of alcohol (entries 9 to 12).

Landscapes

  • 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 un système catalytique comprenant : A) au moins un composé choisi parmi les azoles, les oxazoles, les thiazoles, le benzotriazole, le benzimidazole, le benzoxazole et leurs sels ; B) au moins un piégeur d'acide contenant au moins un groupe époxy ; et C) au moins un catalyseur comprenant une structure amidine N,Ν,Ν'-trisubstituée ayant une teneur en groupes amidine de 12,0 à 47,0 % en poids, exprimé comme CN2 avec un poids moléculaire = 40. Un kit comprend le système catalytique de la présente invention et une dispersion aqueuse d'uretdione ayant un indice d'acide de 1 à 100 mg KOH/g et en outre au moins un groupe carboxyle. L'invention concerne également un procédé pour fabriquer une couche de polyuréthane avec le système catalytique selon la présente invention et ladite dispersion d'uretdione et la couche de polyuréthane ainsi obtenue, ainsi que l'utilisation du système catalytique pour le durcissement de dispersions d'uretdione aqueuses acides et/ou la fabrication de vernis ou de revêtements.
EP19711127.1A 2018-03-23 2019-03-21 Système catalytique pour dispersions d'uretdione Withdrawn EP3768748A1 (fr)

Applications Claiming Priority (16)

Application Number Priority Date Filing Date Title
US15/933,495 US11312881B2 (en) 2018-03-23 2018-03-23 One component polyurethane/allophanate formulations with reactive reducer
US15/933,470 US11292864B2 (en) 2018-03-23 2018-03-23 Compositions using polyuretdione resins
US15/933,553 US10633477B2 (en) 2018-03-23 2018-03-23 Extended pot-life for low temperature curing polyuretdione resins
US15/933,487 US20190292305A1 (en) 2018-03-23 2018-03-23 Uretdione based polyurethane compositions
US15/933,511 US11440988B2 (en) 2018-03-23 2018-03-23 Polyuretdione-containing resin blend compositions
EP18163621.8A EP3543270A1 (fr) 2018-03-23 2018-03-23 Système catalyseur pour dispersions d'uretdions
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
US15/933,527 US20190292296A1 (en) 2018-03-23 2018-03-23 Polyol acid neutralization for low temperature uretdione curing
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
US15/933,475 US11008416B2 (en) 2018-03-23 2018-03-23 Aqueous, curable composition, comprising dispersed uretdione prepolymer, reactant and azolate
US15/933,507 US20190292294A1 (en) 2018-03-23 2018-03-23 One component allophanate formulations through basecoat catalyst migration
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/EP2019/057066 WO2019180129A1 (fr) 2018-03-23 2019-03-21 Système catalytique pour dispersions d'uretdione

Publications (1)

Publication Number Publication Date
EP3768748A1 true EP3768748A1 (fr) 2021-01-27

Family

ID=65767037

Family Applications (14)

Application Number Title Priority Date Filing Date
EP19713667.4A Withdrawn EP3768755A1 (fr) 2018-03-23 2019-03-21 Compositions utilisant des résines polyurétdione
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
EP19713666.6A Withdrawn EP3768754A1 (fr) 2018-03-23 2019-03-21 Compositions de mélange de résines contenant des polyuretdione
EP19711126.3A Pending EP3768750A1 (fr) 2018-03-23 2019-03-21 Compositions aqueuses contenant des groupes uretdione et leur procédé de préparation
EP19713668.2A Pending EP3768756A1 (fr) 2018-03-23 2019-03-21 Neutralisation d'acide polyol pour durcissement d'urétdione à basse température
EP19713670.8A Withdrawn EP3768758A1 (fr) 2018-03-23 2019-03-21 Formulations de polyuréthane/allophanate à un seul composant comprenant un réducteur réactif
EP19711127.1A Withdrawn EP3768748A1 (fr) 2018-03-23 2019-03-21 Système catalytique pour dispersions d'uretdione
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
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
EP19711129.7A Pending EP3768751A1 (fr) 2018-03-23 2019-03-21 Compositions aqueuses contenant des groupes uretdione et procédé pour leur 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
EP19711128.9A Withdrawn EP3768745A1 (fr) 2018-03-23 2019-03-21 Dispersions de polyuréthane contenant de l'urétdione comprenant des groupes hydrophiles

Family Applications Before (6)

Application Number Title Priority Date Filing Date
EP19713667.4A Withdrawn EP3768755A1 (fr) 2018-03-23 2019-03-21 Compositions utilisant des résines polyurétdione
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
EP19713666.6A Withdrawn EP3768754A1 (fr) 2018-03-23 2019-03-21 Compositions de mélange de résines contenant des polyuretdione
EP19711126.3A Pending EP3768750A1 (fr) 2018-03-23 2019-03-21 Compositions aqueuses contenant des groupes uretdione et leur procédé de préparation
EP19713668.2A Pending EP3768756A1 (fr) 2018-03-23 2019-03-21 Neutralisation d'acide polyol pour durcissement d'urétdione à basse température
EP19713670.8A Withdrawn EP3768758A1 (fr) 2018-03-23 2019-03-21 Formulations de polyuréthane/allophanate à un seul composant comprenant un réducteur réactif

Family Applications After (7)

Application Number Title Priority Date Filing Date
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
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
EP19711129.7A Pending EP3768751A1 (fr) 2018-03-23 2019-03-21 Compositions aqueuses contenant des groupes uretdione et procédé pour leur 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
EP19711128.9A Withdrawn EP3768745A1 (fr) 2018-03-23 2019-03-21 Dispersions de polyuréthane contenant de l'urétdione comprenant des groupes hydrophiles

Country Status (3)

Country Link
EP (14) EP3768755A1 (fr)
CN (10) CN111886273A (fr)
WO (15) WO2019183323A1 (fr)

Families Citing this family (3)

* 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
CN116063975A (zh) * 2021-11-02 2023-05-05 浙江华峰合成树脂有限公司 一种聚氨酯胶黏剂及其制备和应用

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
NL126422C (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
ATE251190T1 (de) * 1994-06-06 2003-10-15 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
EP1197506B1 (fr) * 2000-10-13 2006-01-25 Tosoh Corporation Catalysateur pour la préparation d'une composition de scellement à deux composants à base polyuréthane
DE10123417A1 (de) 2001-05-14 2002-11-21 Bayer Ag Verfahren zur Dimerisierung von Isophorondiisocyanat
JP4533745B2 (ja) 2002-07-04 2010-09-01 バイエル・マテリアルサイエンス・アクチェンゲゼルシャフト ウレトジオン基を有する重付加生成物
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
DE10347901A1 (de) * 2003-10-15 2005-05-19 Degussa Ag Polyurethan-Pulverlackbeschichtungen, welche feste uretdiongruppenhaltige Polyadditionsverbindungen enthalten, und ein Verfahren zu ihrer Herstellung
DE10347902A1 (de) * 2003-10-15 2005-05-19 Degussa Ag Feste uretdiongruppenhaltige Polyadditionsverbindungen
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
EP1778778A4 (fr) * 2004-08-12 2011-04-27 King Industries Inc Compositions organometalliques et compositions de revetement
DE102004043540A1 (de) * 2004-09-09 2006-03-30 Bayer Materialscience Ag Niedrigviskose Allophanate mit aktinisch härtbaren Gruppen
DE102004043538A1 (de) * 2004-09-09 2006-03-16 Bayer Materialscience Ag Herstellung von neuen strahlenhärtenden Bindemitteln
DE102004048773A1 (de) * 2004-10-07 2006-04-13 Degussa Ag Hydroxylterminierte uretdiongruppenhaltige Polyurethanverbindungen
DE102004049592A1 (de) * 2004-10-12 2006-05-04 Bayer Materialscience Ag Mit Soft-Touch-Lack beschichtete, verformbare Kunststoffverbundfolien und Kunststoffverbundelemente sowie deren Herstellung
US7135505B2 (en) * 2004-10-25 2006-11-14 Bayer Materialscience Llc Radiation curable coatings based on uretdione polyisocyanates
DE602005010120D1 (de) * 2004-12-15 2008-11-13 Akzo Nobel Coatings Int Bv Thiolfunktionelle verbindungen enthaltende wässrige beschichtungszusammensetzung
DE102004062588A1 (de) * 2004-12-24 2006-07-06 Degussa Ag Hochreaktive uretdiongruppenhaltige Polyurethanzusammensetzungen auf Basis von 1,4-Diisocyanatocyclohexylmethan
DE102005013401A1 (de) * 2005-03-23 2006-09-28 Degussa Ag Niedrigviskose uretdiongruppenhaltige Polyadditionsverbindungen, Verfahren zur Herstellung und Verwendung
DE102005013329A1 (de) * 2005-03-23 2006-11-16 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
ATE548401T1 (de) * 2008-03-20 2012-03-15 Basf Se Polyurethansysteme für die herstellung von polyurethan-sandwichteilen bei geringen formtemperaturen
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
EP2632965B1 (fr) * 2010-10-29 2017-04-26 Lubrizol Advanced Materials, Inc. Dispersions aqueuses cationiques de polyuréthanne
US9051499B2 (en) * 2010-12-08 2015-06-09 Dow Global Technologie Llc Two-part polyurethane adhesive for bonding fiber-reinforced plastics
EP2465886A1 (fr) * 2010-12-16 2012-06-20 Bayer MaterialScience AG Produits de polyaddition de polyisocyanate, leur procédé de fabrication et d'utilisation
EP2683767A1 (fr) * 2011-03-06 2014-01-15 King Industries, Inc. Compositions d'un complexe métal amidine et d'un second composé, compositions de revêtement les comprenant
US8841369B2 (en) * 2011-03-30 2014-09-23 Basf Se Latently reactive polyurethane dispersion with activatable crosslinking
WO2013043333A1 (fr) * 2011-09-21 2013-03-28 Dow Global Technologies Llc Polyuréthanes obtenus à l'aide de mélanges de composés amines tertiaires et d'acides de lewis comme catalyseurs
EP2877509B1 (fr) * 2012-07-26 2018-11-21 Covestro Deutschland AG Dispersion de polyuréthane aqueux contenant 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
HUE048106T2 (hu) * 2015-05-29 2020-05-28 Basf Se Poliuretán-poliizocianurát gyanták hosszú nyitott idejû szálas kompozitokhoz
JP6568996B2 (ja) * 2016-03-09 2019-08-28 旭化成株式会社 ポリイソシアネート組成物、コーティング組成物、水系コーティング組成物、及びコーティング基材

Also Published As

Publication number Publication date
CN111886271A (zh) 2020-11-03
WO2019183304A1 (fr) 2019-09-26
EP3768757A1 (fr) 2021-01-27
WO2019180131A1 (fr) 2019-09-26
WO2019183319A1 (fr) 2019-09-26
WO2019183307A1 (fr) 2019-09-26
WO2019180130A1 (fr) 2019-09-26
CN112105665A (zh) 2020-12-18
EP3768751A1 (fr) 2021-01-27
CN112105666A (zh) 2020-12-18
WO2019180129A1 (fr) 2019-09-26
EP3768759A1 (fr) 2021-01-27
CN111886272B (zh) 2022-11-15
EP3768749A1 (fr) 2021-01-27
WO2019183300A1 (fr) 2019-09-26
CN112004853B (zh) 2023-07-28
EP3768758A1 (fr) 2021-01-27
EP3768753A1 (fr) 2021-01-27
WO2019180127A1 (fr) 2019-09-26
CN111868133A (zh) 2020-10-30
EP3768745A1 (fr) 2021-01-27
WO2019183313A1 (fr) 2019-09-26
EP3768750A1 (fr) 2021-01-27
EP3768754A1 (fr) 2021-01-27
CN111886273A (zh) 2020-11-03
CN112105666B (zh) 2023-05-23
WO2019180128A1 (fr) 2019-09-26
CN111886272A (zh) 2020-11-03
CN111868131A (zh) 2020-10-30
WO2019183308A1 (fr) 2019-09-26
CN112004853A (zh) 2020-11-27
CN112041367A (zh) 2020-12-04
WO2019183305A1 (fr) 2019-09-26
EP3768747A1 (fr) 2021-01-27
EP3768756A1 (fr) 2021-01-27
EP3768755A1 (fr) 2021-01-27
WO2019183330A1 (fr) 2019-09-26
CN112041367B (zh) 2023-05-16
CN111868135A (zh) 2020-10-30
WO2019183323A1 (fr) 2019-09-26
WO2019183315A1 (fr) 2019-09-26
EP3768752A1 (fr) 2021-01-27

Similar Documents

Publication Publication Date Title
EP1736490B1 (fr) Mélange de polymères à partir de polyols de polycarbonate
EP2121787B1 (fr) Dispersions de pur autoréticulantes sans cosolvants
DE102005036654A1 (de) Selbstvernetzende PUR-Dispersionen mit Uretdionstruktur
EP1910437B1 (fr) Dispersions de polyurethane (pur) autoreticulantes
EP1862486B1 (fr) Dispersions en réseau à faible teneur en solvants ou sans solvants à groupes isocyanates bloqués par le pyrazol
EP0959115B1 (fr) Compositions aqueuses de revêtement à base de PUR à deux composants
DE4213527A1 (de) Wäßrige Überzugsmittel für elastische Einbrennlackierungen
WO2009127365A1 (fr) Solutions aqueuses de polyuréthanes pour systèmes polyuréthanes
DE102004002525A1 (de) Beschichtungsmittelzusammensetzung
EP3109269B1 (fr) Dispersions de polyurethane sans uree
EP3768748A1 (fr) Système catalytique pour dispersions d'uretdione
EP1957551B1 (fr) Production d'une dispersion reticulee au moyen de groupes d'isocyanate bloques
EP1854816B1 (fr) Dispersions liquides à répartition granulométrique bimodale
EP1578837B1 (fr) Dispersions hydrophiles de polyurethanne-polyuree
EP3026071A1 (fr) Dispersions de polyuréthane stabilisées
DE4218449A1 (de) Wasserverdünnbare Zweikomponenten-Überzugsmasse, ein Verfahren zu deren Herstellung und deren Verwendung
EP3543270A1 (fr) Système catalyseur pour dispersions d'uretdions
EP0989145B1 (fr) Dispersions de polyurethanne aqueuses à teneur réduite en triéthylamine
EP3543271A1 (fr) Compositions aqueuses contenant des groupes urétdione et son procede de fabrication
EP3590987A1 (fr) Compositions aqueuses contenant des groupes urétdione et leur procédé de production
US20210024679A1 (en) Catalyst system for uretdione dispersions
EP3590988A1 (fr) Compositions aqueuses contenant des groupes urétdione et leur procédé de production

Legal Events

Date Code Title Description
STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: UNKNOWN

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE INTERNATIONAL PUBLICATION HAS BEEN MADE

PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: REQUEST FOR EXAMINATION WAS MADE

17P Request for examination filed

Effective date: 20201023

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR

AX Request for extension of the european patent

Extension state: BA ME

DAV Request for validation of the european patent (deleted)
DAX Request for extension of the european patent (deleted)
STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION HAS BEEN WITHDRAWN

18W Application withdrawn

Effective date: 20221020