EP3768758A1 - Einkomponenten-polyurethan-/allophanatformulierungen mit reaktivem reduktionsmittel - Google Patents

Einkomponenten-polyurethan-/allophanatformulierungen mit reaktivem reduktionsmittel

Info

Publication number
EP3768758A1
EP3768758A1 EP19713670.8A EP19713670A EP3768758A1 EP 3768758 A1 EP3768758 A1 EP 3768758A1 EP 19713670 A EP19713670 A EP 19713670A EP 3768758 A1 EP3768758 A1 EP 3768758A1
Authority
EP
European Patent Office
Prior art keywords
diisocyanate
methyl
polyol
acetate
isocyanato
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Withdrawn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
EP19713670.8A
Other languages
English (en)
French (fr)
Inventor
Alan Ekin
Joseph Pierce
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 US15/933,470 external-priority patent/US11292864B2/en
Priority claimed from EP18163621.8A external-priority patent/EP3543270A1/de
Priority claimed from US15/933,511 external-priority patent/US11440988B2/en
Priority claimed from US15/933,507 external-priority patent/US20190292294A1/en
Priority claimed from US15/933,500 external-priority patent/US10696775B2/en
Priority claimed from US15/933,475 external-priority patent/US11008416B2/en
Priority claimed from US15/933,553 external-priority patent/US10633477B2/en
Priority claimed from US15/933,527 external-priority patent/US20190292296A1/en
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 US15/933,487 external-priority patent/US20190292305A1/en
Priority claimed from EP18163620.0A external-priority patent/EP3543269A1/de
Priority claimed from EP18163625.9A external-priority patent/EP3543271A1/de
Priority claimed from EP18181876.6A external-priority patent/EP3590987A1/de
Priority claimed from EP18181877.4A external-priority patent/EP3590988A1/de
Application filed by Covestro Deutschland AG, Covestro LLC filed Critical Covestro Deutschland AG
Publication of EP3768758A1 publication Critical patent/EP3768758A1/de
Withdrawn legal-status Critical Current

Links

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
    • C08G18/78—Nitrogen
    • C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
    • C08G18/798—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing urethdione groups
    • 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
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    • 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
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    • 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
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    • 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
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    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
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    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
    • C08G18/3225—Polyamines
    • C08G18/3234—Polyamines cycloaliphatic
    • 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
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    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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    • 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, in general to polymers, and more specifically, to one component, polyurethane/allophanate clear-coat compositions used in conjunction with a basecoat and a reactive reducer.
  • the reactive reducer contains a tertiary amine catalyst for a possible dual role of catalyzing the clear-coat and neutralizing the basecoat, if necessary.
  • Polyurethane-forming compositions are widely used in a variety of commercial, industrial and household applications, such as in automotive clear-coat and seat cushion applications.
  • Polyurethane systems that employ isocyanates which are pre-reacted with monofunctional reagents to form relatively thermally labile compounds are called blocked isocyanates.
  • Uretdiones are a type of blocked isocyanate.
  • Uretdiones are typically prepared by dimerizing isocyanate to form uretdione(s) with unreacted isocyanate end-groups which can then be extended with a polyol to form a polymeric material containing two or more uretdione groups in the polymer chain.
  • uretdiones are referred to as“1 ,3-diaza-2,4- cyclobutanones”,“1 ,3-diazatidin-2,4-diones”,“2,4-dioxo-1 ,3-diazetidines”, “urethdiones” or“uretidiones”.
  • the polymer has few, if any, free isocyanate groups, which is achieved by controlling the stoichiometry of the polyisocyanate, polyol and by the use of a blocking agent.
  • Polyuretdiones may react with polyols in the presence of tertiary amine catalysts and thus do not form stable systems in terms of shelf-life. Therefore, polyuretdiones and polyols cannot form stable one component systems in the presence of suitable tertiary amine catalysts.
  • the tertiary amine catalyst is attracted to the acidic basecoat due to acidity differences between the clear-coat and the basecoat. If an excess amount of catalyst is added to the clear-coat to both catalyze the clear-coat and to neutralize the basecoat; then very short pot-life is provided for the clear-coat.
  • no one has developed a cross-linking approach using a one component clear-coat composition in conjunction with an optional basecoat using a reactive reducer.
  • the present invention attempts to alleviate problems inherent in the art by providing an alternative cross-linking approach to obtain compositions having physical properties similar to those of polyurethane compositions.
  • Various embodiments of the inventive approach involve crosslinking polyuretdione resins with neutralized polyols in the presence of a reactive reducer containing a reducing agent and a tertiary amine catalyst. The reaction between the polyol and the
  • polyuretdione will proceed once the reactive reducer has reduced the viscosity of the formulation to appropriate levels.
  • clear-coat curing is improved as the reactive reducer reduces the viscosity of the basecoat and at the same time neutralizes the basecoat, if necessary.
  • the basecoat does not require a neutralizer, the presence of tertiary amine in the basecoat can help with clear-coat curing by migrating to the clear-coat.
  • a range of "1 .0 to 10.0" is intended to include all sub-ranges between (and including) the recited minimum value of 1 .0 and the recited maximum value of 10.0, that is, having a minimum value equal to or greater than 1 .0 and a maximum value equal to or less than 10.0, such as, for example, 2.4 to 7.6.
  • Any maximum numerical limitation recited in this specification is intended to include all lower numerical limitations subsumed therein and any minimum numerical limitation recited in this specification is intended to include all higher numerical limitations subsumed therein. Accordingly, Applicant reserves the right to amend this specification, including the claims, to expressly recite any sub-range subsumed within the ranges expressly recited herein.
  • compositions and methods are described in terms of “comprising” various components or steps, the compositions and methods can also“consist essentially of” or“consist of” the various components or steps.
  • the present invention provides a clear- coat composition comprising a neutralized polyol; a polyuretdione resin; and a reactive reducer comprising a tertiary amine catalyst and a reducing agent.
  • the present invention provides a method of making a clear-coat comprising combining a polyuretdione resin and a neutralized polyol in the presence of a reactive reducer comprising a tertiary amine catalyst and a reducing agent.
  • the present invention also provides a one component composition comprising: a neutralized polyol; a polyuretdione resin; and a reducing agent, wherein the composition has a storage stability of at least 14 months, as measured by viscosity increase.
  • the present invention provides an allophanate polymer system made by a method comprising combining a neutralized polyol with a polyuretdione resin in the presence of a reactive reducer comprising a tertiary amine catalyst and a reducing agent to produce a clear-coat, and contacting the clear-coat with a basecoat comprising a tertiary amine catalyst.
  • the same or a different, reactive reducer may be used to reduce the viscosity of the basecoat and comprises a tertiary amine catalyst that acts as a neutralizer for acidic groups within the basecoat, if necessary.
  • the polyuretdione and polyol of the formulations can be supplied together which makes them one component. The reaction between polyol and polyuretdione will proceed after the reactive reducer has reduced the viscosity of the formulation to an appropriate level.
  • the reactive reducer contains a reducing agent (solvent) and a catalyst.
  • the inventive allophanate polymer system is particularly applicable in producing coatings, adhesives, castings, composites, and sealants.
  • polymer encompasses prepolymers, oligomers and both homopolymers and copolymers; the prefix “poly” in this context referring to two or more.
  • molecular weight when used in reference to a polymer, refers to the number average molecular weight, unless otherwise specified.
  • polyol refers to compounds comprising at least two free hydroxy groups. Polyols include polymers comprising pendant and terminal hydroxy groups.
  • coating composition refers to a mixture of chemical components that will cure and form a coating when applied to a substrate.
  • adheresive or “adhesive compound” refer to any substance that can adhere or bond two items together. Implicit in the definition of an "adhesive composition” or “adhesive formulation” is the concept that the composition or formulation is a combination or mixture of more than one species, component or compound, which can include adhesive monomers, oligomers, and polymers along with other materials.
  • A“sealant composition” refers to a composition which may be applied to one or more surfaces to form a protective barrier, for example to prevent ingress or egress of solid, liquid or gaseous material or alternatively to allow selective permeability through the barrier to gas and liquid. In particular, it may provide a seal between surfaces.
  • A“casting composition” refers to a mixture of liquid chemical components which is usually poured into a mold containing a hollow cavity of the desired shape, and then allowed to solidify.
  • A“composite” refers to a material made from two or more polymers, optionally containing other kinds of materials. A composite has different properties from those of the individual polymers/materials which make it up.
  • "Cured,” “cured composition” or “cured compound” refers to components and mixtures obtained from reactive curable original compound(s) or mixture(s) thereof which have undergone a chemical and/or physical changes such that the original compound(s) or mixture(s) is(are) transformed into a solid, substantially non-flowing material.
  • a typical curing process may involve crosslinking.
  • curable means that an original compound(s) or composition material(s) can be transformed into a solid, substantially non flowing material by means of chemical reaction, crosslinking, radiation crosslinking, or the like.
  • compositions of the invention are curable, but unless otherwise specified, the original compound(s) or composition material(s) is (are) not cured.
  • basecoat means the first (undermost) layer applied to the surface of a substrate prior to application of a subsequent or finishing coat.
  • the term encompasses basecoats, undercoats, and tiecoats.
  • the components useful in the present invention comprise a polyisocyanate.
  • polyisocyanate refers to compounds comprising at least two unreacted isocyanate groups, such as three or more unreacted isocyanate groups.
  • the polyisocyanate may comprise diisocyanates such as linear aliphatic polyisocyanates, aromatic polyisocyanates, cycloaliphatic polyisocyanates and aralkyl
  • uretdiones particularly preferred are those blocked isocyanates known as uretdiones.
  • the uretdiones useful in the invention may be obtained by catalytic dimerization of polyisocyanates by methods which are known to those skilled in the art.
  • dimerization catalysts include, but are not limited to, trialkylphosphines,
  • aminophosphines and aminopyradines such as dimethylaminopyridines, and tris(dimethylamino)phosphine, as well as any other dimerization catalyst.
  • the result of the dimerization reaction depends, in a manner known to the skilled person, on the catalyst used, on the process conditions and on the polyisocyanates employed.
  • products it is possible for products to be formed which contain on average more than one uretdione group per molecule, the number of uretdione groups being subject to a distribution.
  • the (poly)uretdiones may optionally contain isocyanurate, biuret, allophanate, and iminooxadiazine dione groups in addition to the uretdione groups.
  • the uretdiones are NCO-functional compounds and may be subjected to a further reaction, for example, blocking of the free NCO groups or further reaction of NCO groups with NCO-reactive compounds having a functionality of two or more to extend the uretdiones to form polyuretdione prepolymers.
  • Suitable blocking agents include, but are not limited to, alcohols, lactams, oximes, malonates, alkyl acetoacetates, triazoles, phenols, imidazoles, pyrazoles and amines, such as butanone oxime,
  • diisopropylamine 1 ,2,4-triazole, dimethyl-1 ,2,4-triazole, imidazole, diethyl malonate, ethyl acetoacetate, acetone oxime, 3,5-dimethylpyrazole, caprolactam, N-tert-butylbenzylamine and cyclopentanone including mixtures of these blocking agents.
  • NCO-reactive compounds with a functionality of two or more include polyols.
  • the NCO-reactive compounds are used in amounts sufficient to react with all free NCO groups in the uretdione.
  • free NCO groups it is meant all NCO groups not present as part of the uretdione, isocyanurate, biuret, allophanate and iminooxadiazine dione groups.
  • the resulting polyuretdione contains at least 2, such as from 2 to 10 uretdione groups. More preferably, the polyuretdione contains from 5% to 45% uretdione, 10% to 55% urethane, and less than 2% isocyanate groups. The percentages are by weight based on total weight of resin containing uretdione, urethane, and isocyanate.
  • Suitable polyisocyanates for producing the uretdiones useful in embodiments of the invention include, organic diisocyanates represented by the formula
  • R represents an organic group obtained by removing the isocyanate groups from an organic diisocyanate having (cyclo)aliphatically bound isocyanate groups and a molecular weight of 1 12 to 1000, preferably 140 to 400.
  • Preferred diisocyanates for the invention are those
  • R represents a divalent aliphatic hydrocarbon group having from 4 to 18 carbon atoms, a divalent cycloaliphatic hydrocarbon group having from 5 to 15 carbon atoms, or a divalent araliphatic hydrocarbon group having from 7 to 15 carbon atoms.
  • 1 ,6-hexamethylene diisocyanate (HDI), 2,2,4-trimethyl-1 ,6-hexamethylene diisocyanate, 1 ,12-dodecamethylene diisocyanate, cyclohexane-1 ,3- and 1 ,4-diisocyanate, 1 -isocyanato-2-isocyanato-methyl cyclopentane, 1 - isocyanato-3-isocyanatomethyl-3, 5, 5-trimethyl cyclohexane (isophorone diisocyanate or IPDI), bis-(4-isocyanatocyclohexyl)methane, 1 ,3- and 1 ,4- bis(isocyanatomethyl)-cyclohexane, bis-(4-isocyanato-3-methyl- cyclohexyl)-methane, a,a,a',a'-tetramethyl-1 ,3- and 1 ,4-xylene
  • diisocyanate 1 -isocyanato-1 -methyl-4(3)-isocyanato-methyl cyclohexane, and 2,4- and 2,6-hexahydrotoluene diisocyanate, toluene diisocyanate (TDI), diphenylmethane diisocyanate (MDI), pentane diisocyanate (PDI) - bio-based, and, isomers of any of these; or combinations of any of these. Mixtures of diisocyanates may also be used.
  • Preferred diisocyanates include 1 ,6-hexamethylene diisocyanate, isophorone diisocyanate, and bis(4-isocyanatocyclohexyl)-methane because they are readily available and yield relatively low viscosity polyuretdione polyurethane oligomers.
  • the uretdiones may comprise from 35% to 85% resin solids in the composition of present invention, excluding solvents, additives or pigments. In other embodiments, from 50% to 85% and in still other embodiments, 60% to 85%.
  • the uretdiones may comprise any resin solids amount ranging between any combinations of these values, inclusive of the recited values.
  • the polyols useful in the present invention may be either low molecular weight (65-399 Da, as determined by gel permeation
  • the polyol of the present invention includes low molecular weight diols, triols and higher alcohols and polymeric polyols such as polyester polyols, polyether polyols, polycarbonate polyols, polyurethane polyols and hydroxy-containing (meth)acrylic polymers.
  • the low molecular weight diols, triols and higher alcohols useful in the instant invention are known to those skilled in the art. In many embodiments, they are monomeric and have hydroxy values of 200 and above, usually within the range of 1500 to 200.
  • Such materials include aliphatic polyols, particularly alkylene polyols containing from 2 to 18 carbon atoms. Examples include ethylene glycol, 1 ,4-butanediol, 1 ,6- hexanediol; cycloaliphatic polyols such as cyclohexane dimethanol.
  • triols and higher alcohols include trimethylol propane and pentaerythritol. Also useful are polyols containing ether linkages such as diethylene glycol and triethylene glycol.
  • the suitable polyols are polymeric polyols having hydroxyl values less than 200, such as 10 to 180. Examples of polymeric polyols include polyalkylene ether polyols, polyester polyols including hydroxyl-containing polycaprolactones, hydroxy-containing (meth)acrylic polymers, polycarbonate polyols and polyurethane polymers.
  • polyether polyols examples include poly(oxytetramethylene) glycols, poly(oxyethylene) glycols, and the reaction product of ethylene glycol with a mixture of propylene oxide and ethylene oxide.
  • polyether polyols formed from the oxyalkylation of various polyols, for example, glycols such as ethylene glycol, 1 ,4-butane glycol, 1 ,6-hexanediol, and the like, or higher polyols, such as trimethylol propane, pentaerythritol and the like.
  • glycols such as ethylene glycol, 1 ,4-butane glycol, 1 ,6-hexanediol, and the like
  • polyols such as trimethylol propane, pentaerythritol and the like.
  • alkylene oxide for example, ethylene oxide in the presence of an acidic or basic catalyst.
  • Polyester polyols can also be used as a polymeric polyol component in the certain embodiments of the invention.
  • the polyester polyols can be prepared by the polyesterification of organic polycarboxylic acids or anhydrides thereof with organic polyols.
  • the polyester polyols Preferably, the
  • polycarboxylic acids and polyols are aliphatic or aromatic dibasic acids and diols.
  • the diols which may be employed in making the polyester include alkylene glycols, such as ethylene glycol and butylene glycol, neopentyl glycol and other glycols such as cyclohexane dimethanol, caprolactone diol (for example, the reaction product of caprolactone and ethylene glycol), polyether glycols, for example, poly(oxytetramethylene) glycol and the like.
  • alkylene glycols such as ethylene glycol and butylene glycol
  • neopentyl glycol and other glycols such as cyclohexane dimethanol
  • caprolactone diol for example, the reaction product of caprolactone and ethylene glycol
  • polyether glycols for example, poly(oxytetramethylene) glycol and the like.
  • other diols of various types and, as indicated, polyols of higher functionality may also be utilized in various embodiments of the invention.
  • Such higher polyols can include, for example, trimethylol propane, trimethylol ethane, pentaerythritol, and the like, as well as higher molecular weight polyols such as those produced by oxyalkylating low molecular weight polyols.
  • An example of such high molecular weight polyol is the reaction product of 20 moles of ethylene oxide per mole of trimethylol propane.
  • the acid component of the polyester consists primarily of monomeric carboxylic acids or anhydrides having 2 to 18 carbon atoms per molecule.
  • the acids which are useful are phthalic acid, isophthalic acid, terephthalic acid, tetrahydrophthalic acid, hexahydrophthalic acid, adipic acid, azelaic acid, sebacic acid, maleic acid, glutaric acid, chlorendic acid, tetrachlorophthalic acid and other dicarboxylic acids of varying types.
  • polycarboxylic acids such as trimellitic acid and tricarballylic acid (propane-1 ,2,3-tricarboxylic acid).
  • polyester polyols formed from polybasic acids and polyols polycaprolactone-type polyesters can also be employed. These products are formed from the reaction of a cyclic lactone such as e-caprolactone with a polyol with primary hydroxyls such as those mentioned above. Such products are described in U.S. Pat. No. 3,169,949.
  • hydroxy- containing (meth)acrylic polymers or (meth)acrylic polyols can be used as the polyol component.
  • the (meth)acrylic polymers are polymers of 2 to 20 percent by weight primary hydroxy-containing vinyl monomers such as hydroxyalkyl acrylate and methacrylate having 2 to 6 carbon atoms in the alkyl group and 80 to 98 percent by weight of other ethylenically
  • alkyl(meth)acrylates unsaturated copolymerizable materials
  • alkyl(meth)acrylates unsaturated copolymerizable materials
  • the percentages by weight being based on the total weight of the monomeric charge.
  • suitable hydroxy alkyl(meth)acrylates are hydroxy ethyl and hydroxy butyl(meth)acrylate.
  • suitable alkyl acrylates and (meth)acrylates are lauryl methacrylate, 2-ethylhexyl methacrylate and n-butyl acrylate.
  • copolymerizable monomers which can be copolymerized with the hydroxyalkyl (meth)acrylates include ethylenically unsaturated materials such as monoolefinic and diolefinic hydrocarbons, halogenated
  • monoolefinic and diolefinic hydrocarbons unsaturated esters of organic and inorganic acids, amides and esters of unsaturated acids, nitriles and unsaturated acids and the like.
  • monomers include styrene, 1 ,3-butadiene, acrylamide, acrylonitrile, a-methyl styrene, a-methyl chlorostyrene, vinyl butyrate, vinyl acetate, alkyl chloride, divinyl benzene, diallyl itaconate, triallyl cyanurate and mixtures thereof.
  • these other ethylenically unsaturated materials are used in admixture with the above-mentioned acrylates and methacrylates.
  • the polyol may be a polyurethane polyol.
  • These polyols can be prepared by reacting any of the above-mentioned polyols with a minor amount of polyisocyanate (OH/NCO equivalent ratio greater than 1 :1 ) so that free primary hydroxyl groups are present in the product.
  • polyisocyanate OH/NCO equivalent ratio greater than 1 :1
  • mixtures of both high molecular weight and low molecular weight polyols such as those mentioned above may be used.
  • Suitable hydroxy-functional polycarbonate polyols may be those prepared by reacting monomeric diols (such as 1 ,4-butanediol, 1 ,6- hexanediol, di-, tri- or tetraethylene glycol, di-, tri- or tetrapropylene glycol, 3-methyl-1 ,5-pentanediol, 4,4'-dimethylolcyclohexane and mixtures thereof) with diaryl carbonates (such as diphenyl carbonate, dialkyl carbonates (such as dimethyl carbonate and diethyl carbonate), alkylene carbonates (such as ethylene carbonate or propylene carbonate), or phosgene.
  • monomeric diols such as 1 ,4-butanediol, 1 ,6- hexanediol, di-, tri- or tetraethylene glycol, di-, tri- or tetrapropylene glycol, 3-methyl
  • the polyol is N-(2-aminoethyl)-2-aminoethyl
  • Acid scavengers should be covalently bonded to the acidic groups within the polyol.
  • Acid scavengers may be selected from carbodiimides, anhydrides, epoxies, trialkylorthoformates, amine compounds, or oxazolines. The present inventors believe, without wishing to be bound to any specific theory, that these acid scavengers covalently bind to carboxylic and acrylic acid groups within the polyols.
  • Such compounds are commercially available from a variety of suppliers, such as for example, the monomeric carbodiimides sold under the STABAXOL trade name from Rhein Chemie, and bis(2,6-diisopropylphenyl) carbodiimide sold as EUSTAB HS-700 by Eutec Chemical Co., Ltd.
  • Urethane reducing agents come in slow, medium and fast formulations, and may improve atomization, flow and leveling, which helps to provide a smooth finish with less "orange peel” effect.
  • the reducing agent of the present invention may contain various combinations of compounds including, but not limited to, n- butyl acetate, ethyl acetate, 2-methoxy-1 -methylethyl acetate, 1 -methoxy-2- propyl acetate, 2-methoxy-1 -propyl acetate, 2-ethoxyethyl acetate, n- heptane, methylcyclohexane, toluene, acetone, Varnish Makers and Painter (VM&P) naphtha, naphtha, light aliphatic solvent naphtha, acetate, isobutyl acetate, mixed xylenes, ethylbenzene, methyl eth
  • V&P Varnish Makers and Painter
  • suitable solvents include, but are not limited to aliphatic and aromatic hydrocarbons such as toluene, xylene, isooctane, acetone, butanone, methyl ethyl ketone, methyl amyl ketone, methyl isobutyl ketone, ethyl acetate, butyl acetate, pentyl acetate,
  • aliphatic and aromatic hydrocarbons such as toluene, xylene, isooctane, acetone, butanone, methyl ethyl ketone, methyl amyl ketone, methyl isobutyl ketone, ethyl acetate, butyl acetate, pentyl acetate,
  • the clear-coat composition of the invention may be contacted with the basecoat by any methods known to those skilled in the art, including but not limited to, spraying, dipping, flow coating, rolling, brushing, pouring, and the like.
  • the clear-coat compositions may be applied in the form of paints or lacquers onto any compatible substrate, such as, for example, metals, plastics, ceramics, glass, and natural materials.
  • the clear-coat composition is applied as a single layer. In other embodiments, it may be applied as multiple layers as needed.
  • the reaction between the polyol and the polyuretdione will proceed once the reactive reducer has reduced the viscosity of the formulation to appropriate levels.
  • clear-coat curing is improved as the reactive reducer reduces the viscosity of the basecoat and at the same time neutralizes the basecoat, if necessary.
  • the basecoat does not require a neutralizer, the presence of tertiary amine in the basecoat can help with clear-coat curing by migrating to the clear-coat.
  • the embodiments of the present invention described herein contain the same reactive reducer in the clear-coat composition and the basecoat, the present invention is not to be so limited.
  • the clear-coat composition and the basecoat may contain the same reactive reducer and in other embodiments they may contain different reactive reducers.
  • POLYOL A an aromatic free, branched hydroxyl-bearing polyester polyol, commercially available from Covestro as DESMOPHEN 775 XP;
  • ADDITIVE B a surface additive on polyacrylate-basis for solvent-borne coating systems and printing inks, commercially available from BYK Chemie as BYK 358N;
  • URETDIONE A a 1 -isocyanato-3-isocyanatomethyl-3, 5,5- trimethyl cyclohexane (isophorone diisocyanate or IPDI)-based uretdione, commercially available from Covestro as CRELAN EF 403; REDUCER A a universal medium reducer, commercially
  • REACTIVE REDUCER B 150 parts REDUCER A and the listed amount of
  • BASECOAT B 100 parts BASECOAT A and 50 parts
  • REACTIVE REDUCER B was added to both BASECOAT B and CLEAR-COAT A just before spray application.
  • BASECOAT B was spray applied with a conventional high- volume, low-pressure (HVLP) sprayer over PRIMER A.
  • HVLP high- volume, low-pressure
  • CLEAR-COAT FORMULATION A was prepared as follows. POLYOL A was reacted with ADDITIVE A prior to formulation. In a 500 mL plastic container 14.17 parts of POLYOL A and ADDITIVE A mixture, 0.57 parts ADDITIVE B, 7.90 parts n-butyl acetate (“n-BA”), 96.61 parts
  • URETDIONE A were added. The resulting mixture was mixed using a FLACKTEK speed mixer for one minute. Just prior to spraying, 100 parts REACTIVE REDUCER B was added to CLEAR-COAT A and mixed with a FLACKTEK speed mixer for one minute. This mixture was spray applied using a conventional HVLP sprayer.
  • Iron phosphate-treated ACT B1000 4”x12” (10.2 cm x 30.5 cm) test panels were sprayed with PRIMER A (polyurethane automotive primer) before receiving BASECOAT followed by CLEAR-COAT A.
  • the thickness of the black polyester BASECOAT A was 2 mils (50 pm) wet and the thickness of CLEAR-COAT A was 5 mils (125 pm) wet (2 mils (50 pm) dry).
  • the resulting panels were tested for microhardness and MEK double rubs and the results are summarized in Table I.
  • Films were cured at room temperature (21 O - 240) for one day, three days, one week, three weeks, and five weeks before testing.
  • Microhardness (Marten’s hardness) measurements were done using FISCHERSCOPE H100C instrument with the method described in DIN EN ISO 14577. Microhardness readings were taken under a 20 mN test load run to a maximum of 5 pm indentation depths over a 20-second application time. Results reported are an average of three readings for each formulation.
  • MEK double rubs were measured according to ASTM D4752- 10(2015). Results reported are an average of three readings for each formulation.
  • Table II summarizes the viscosities of the Formulation A (clear- coat only) from Table I. Viscosities were measured according to ASTM D7395-07(2012) using a BROOKFIELD RST Rheometer at 250, 100 s-1 shear rate for two minutes with a RST-50-1 spindle.“Initial viscosity” refers to the viscosity of the composition at the time it was made and“14 month viscosity” refers to the viscosity of the composition after 14 months of being stored at room temperature.
  • REACTIVE REDUCER B was prepared using REDUCER A and catalyst.
  • Formulation A did not contain any catalyst; therefore, it was a control formulation for both basecoat and clear-coat.
  • Formulations B, C, and D contained increasing levels of catalyst.
  • Formulation A had very poor performance in terms of microhardness and MEK double rubs.
  • the performance of coating increased as the amount of catalyst in REACTIVE REDUCER B was increased (Formulations B through D).
  • Formulations B and C had enough levels of catalyst for clear-coat; however, not enough catalyst to act as a neutralizer for basecoat.
  • Formulation D had enough amount of catalyst to catalyze clear-coat and to neutralize basecoat.
  • the present inventors postulate that the catalyst may play a dual role; a) to catalyze clear-coat and b) to neutralize the acidic basecoat.
  • Table II summarizes the viscosities of Formulation A (clear-coat only) and establishes its storage stability.
  • the one component clear-coat had all the components mixed except the catalyst.
  • the inventive formulation can be supplied as one component, it was stored at room temperature for 14 months. It is apparent to those skilled in the art that the viscosity of the formulation showed no signs of viscosity increase over that time, thus demonstrating that the inventive coating can be stored as one component for an extended time.
  • the one component allophanate polymers produced by the present invention are believed to be particularly applicable for coatings, adhesives, castings, composites, and sealants.
  • a clear-coat composition comprising: a neutralized polyol; a polyuretdione resin; and a reactive reducer comprising a reducing agent and a tertiary amine catalyst.
  • cyclohexane isophorone diisocyanate or IPDI
  • IPDI isophorone diisocyanate
  • bis-(4- isocyanatocyclohexyl)methane 1 ,3- and 1 ,4-bis(isocyanatomethyl)- cyclohexane, bis-(4-isocyanato-3-methyl-cyclohexyl)-methane, a,a,a',a'- tetram ethyl -1 ,3- and 1 ,4-xylene diisocyanate, 1 -isocyanato-1 -methyl-4(3)- isocyanato-methyl cyclohexane, and 2,4- and 2,6-hexahydrotoluene diisocyanate, toluene diisocyanate (TDI), diphenylmethane diisocyanate (MDI), pentane diisocyanate (PDI) - bio-
  • the reactive reducer contains one selected from the group consisting of 1 ,8-diazabicyclo[5.4.0]undec-7-ene, 7-methyl-1 ,5,7- triazabicyclo[4.4.0]dec-5-ene, 1 ,4,5,6-tetrahydro-1 ,2-dimethylpyrimidine,
  • 1 1 A method of applying the clear-coat composition made according to one of clauses 1 to 10 to a substrate, wherein the method comprises at least one of spraying, dipping, flow coating, rolling, brushing, and pouring.
  • a one component composition comprising: a neutralized polyol; a polyuretdione resin; and a reducing agent, wherein the
  • composition has a storage stability of at least 14 months, as measured by viscosity increase.
  • a method of making a clear-coat composition comprising: combining a polyuretdione resin and a neutralized polyol in the presence of a reactive reducer comprising a reducing agent and a tertiary amine catalyst.
  • polyol is selected from the group consisting of polyalkylene ether polyols, polyester polyols, hydroxyl containing polycaprolactones, hydroxyl-containing (meth)acrylic polymers, polycarbonate polyols, polyurethane polyols, and combinations thereof.
  • polyuretdione resin comprises the reaction product of catalytic dimerization of an isocyanate.
  • 1 ,6-hexamethylene diisocyanate (HDI), 2,2,4-trimethyl-1 ,6-hexamethylene diisocyanate, 1 ,12-dodecamethylene diisocyanate, cyclohexane-1 ,3- and 1 ,4-diisocyanate, 1 -isocyanato-2-isocyanato-methyl cyclopentane, 1 - isocyanato-3-isocyanatomethyl-3, 5, 5-trimethyl cyclohexane (isophorone diisocyanate or IPDI), bis-(4-isocyanatocyclohexyl)methane, 1 ,3- and 1 ,4- bis(isocyanatomethyl)-cyclohexane, bis-(4-isocyanato-3-methyl- cyclohexyl)-methane, a,a,a',a'-tetramethyl-1 ,3- and 1 ,4-xylene
  • TDI toluene diisocyanate
  • MDI diphenylmethane diisocyanate
  • PDI pentane diisocyanate
  • the reactive reducer contains one selected from the group consisting of 1 ,8- diazabicyclo[5.4.0]undec-7-ene, 7-methyl-1 ,5,7-triazabicyclo[4.4.0]dec-5- ene, 1 ,4,5,6-tetrahydro-1 ,2-dimethylpyrimidine, 1 ,2,4-triazole, sodium derivative and 2-tert-butyl-1 ,1 ,3,3-tetramethylguanidine, and combinations thereof.
  • An allophanate polymer system made by a method comprising: combining a neutralized polyol with a polyuretdione resin in the presence of a reactive reducer comprising a reducing agent and a tertiary amine catalyst to produce a clear-coat, and contacting the clear-coat with a basecoat comprising a reactive reducer which is the same as or different from the reactive reducer in the clear-coat.
  • an additive package selected from the group consisting of flow control additives, wetting agents, and a solvent.
  • polyuretdione resin comprises the reaction product of catalytic dimerization of an isocyanate.
  • the reducing agent is selected from the group consisting of n-butyl acetate, ethyl acetate, 2-methoxy-1 -methylethyl acetate, 1 - methoxy-2-propyl acetate, 2-methoxy-1 -propyl acetate, 2-ethoxyethyl acetate, n-heptane, methylcyclohexane, toluene, acetone, VM&P naphtha, naphtha, light aliphatic solvent naphtha, acetate, isobutyl acetate, mixed xylenes, ethylbenzene, methyl ethyl ketone, dimethyl ketone, methyl n-amyl ketone, methyl isobutyl ketone, 1 ,2,4 trimethyl benzene, isopropylbenzene, ethyl benzene, 1 -chloro-4 (trif
  • the neutralized polyol comprises the reaction product of a polyol and an acid scavenger.
  • the contacting comprises at least one of spraying, dipping, flow coating, rolling, brushing, and pouring.

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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)
EP19713670.8A 2018-03-23 2019-03-21 Einkomponenten-polyurethan-/allophanatformulierungen mit reaktivem reduktionsmittel Withdrawn EP3768758A1 (de)

Applications Claiming Priority (16)

Application Number Priority Date Filing Date Title
EP18163621.8A EP3543270A1 (de) 2018-03-23 2018-03-23 Katalysatorsystem für uretdiondispersionen
US15/933,487 US20190292305A1 (en) 2018-03-23 2018-03-23 Uretdione based polyurethane compositions
US15/933,500 US10696775B2 (en) 2018-03-23 2018-03-23 Curing for polyallophanate compositions through undercoat acid neutralization
US15/933,475 US11008416B2 (en) 2018-03-23 2018-03-23 Aqueous, curable composition, comprising dispersed uretdione prepolymer, reactant and azolate
US15/933,553 US10633477B2 (en) 2018-03-23 2018-03-23 Extended pot-life for low temperature curing polyuretdione resins
US15/933,527 US20190292296A1 (en) 2018-03-23 2018-03-23 Polyol acid neutralization for low temperature uretdione curing
US15/933,470 US11292864B2 (en) 2018-03-23 2018-03-23 Compositions using polyuretdione resins
US15/933,511 US11440988B2 (en) 2018-03-23 2018-03-23 Polyuretdione-containing resin blend compositions
US15/933,507 US20190292294A1 (en) 2018-03-23 2018-03-23 One component allophanate formulations through basecoat catalyst migration
EP18163620.0A EP3543269A1 (de) 2018-03-23 2018-03-23 Uretdionhaltige polyurethandispersionen mit hydrophilen gruppen
EP18163625.9A EP3543271A1 (de) 2018-03-23 2018-03-23 Wässrige uretdiongruppenhaltige zusammensetzungen und verfahren zu deren herstellung
US15/933,570 US10731051B2 (en) 2018-03-23 2018-03-23 Basecoat acid neutralization through inorganic salts
US15/933,495 US11312881B2 (en) 2018-03-23 2018-03-23 One component polyurethane/allophanate formulations with reactive reducer
EP18181876.6A EP3590987A1 (de) 2018-07-05 2018-07-05 Wässrige uretdiongruppenhaltige zusammensetzungen und verfahren zu deren herstellung
EP18181877.4A EP3590988A1 (de) 2018-07-05 2018-07-05 Wässrige uretdiongruppenhaltige zusammensetzungen und verfahren zu deren herstellung
PCT/US2019/023325 WO2019183323A1 (en) 2018-03-23 2019-03-21 One component polyurethane/allophanate formulations with reactive reducer

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Publication Number Publication Date
EP3768758A1 true EP3768758A1 (de) 2021-01-27

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Family Applications (14)

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EP19713339.0A Pending EP3768752A1 (de) 2018-03-23 2019-03-21 Neutralisierung der basisschicht durch anorganische salze
EP19713668.2A Pending EP3768756A1 (de) 2018-03-23 2019-03-21 Polyolsäureneutralisierung zur uretdionhärtung bei niedriger temperatur
EP19713669.0A Withdrawn EP3768757A1 (de) 2018-03-23 2019-03-21 Einkomponentige allophanatformulierungen durch grundschicht-katalysatormigration
EP19711128.9A Withdrawn EP3768745A1 (de) 2018-03-23 2019-03-21 Uretdionhaltige polyurethandispersionen mit hydrophilen gruppen
EP19713663.3A Withdrawn EP3768747A1 (de) 2018-03-23 2019-03-21 Wässrige, härtbare zusammensetzung mit dispergiertem uretdion-präpolymer, reaktand und azolat
EP19711129.7A Pending EP3768751A1 (de) 2018-03-23 2019-03-21 Wässrige uretdiongruppenhaltige zusammensetzungen und verfahren zu deren herstellung
EP19711126.3A Pending EP3768750A1 (de) 2018-03-23 2019-03-21 Wässrige uretdiongruppenhaltige zusammensetzungen und verfahren zu deren herstellung
EP19713667.4A Withdrawn EP3768755A1 (de) 2018-03-23 2019-03-21 Zusammensetzungen mit polyuretdionharzen
EP19711127.1A Withdrawn EP3768748A1 (de) 2018-03-23 2019-03-21 Katalysatorsystem für uretdiondispersionen
EP19713670.8A Withdrawn EP3768758A1 (de) 2018-03-23 2019-03-21 Einkomponenten-polyurethan-/allophanatformulierungen mit reaktivem reduktionsmittel
EP19713665.8A Withdrawn EP3768753A1 (de) 2018-03-23 2019-03-21 Verbesserte härtung für polyallophanatzusammensetzungen durch säureneutralisierung der grundierung
EP19713666.6A Withdrawn EP3768754A1 (de) 2018-03-23 2019-03-21 Polyuretdionhaltige harzmischungszusammensetzungen
EP19714972.7A Withdrawn EP3768759A1 (de) 2018-03-23 2019-03-21 Verlängerte topfzeit für niedrigtemperaturhärtende polyuretdionharze
EP19711125.5A Pending EP3768749A1 (de) 2018-03-23 2019-03-21 Wässrige uretdiongruppenhaltige zusammensetzungen und verfahren zu deren herstellung

Family Applications Before (9)

Application Number Title Priority Date Filing Date
EP19713339.0A Pending EP3768752A1 (de) 2018-03-23 2019-03-21 Neutralisierung der basisschicht durch anorganische salze
EP19713668.2A Pending EP3768756A1 (de) 2018-03-23 2019-03-21 Polyolsäureneutralisierung zur uretdionhärtung bei niedriger temperatur
EP19713669.0A Withdrawn EP3768757A1 (de) 2018-03-23 2019-03-21 Einkomponentige allophanatformulierungen durch grundschicht-katalysatormigration
EP19711128.9A Withdrawn EP3768745A1 (de) 2018-03-23 2019-03-21 Uretdionhaltige polyurethandispersionen mit hydrophilen gruppen
EP19713663.3A Withdrawn EP3768747A1 (de) 2018-03-23 2019-03-21 Wässrige, härtbare zusammensetzung mit dispergiertem uretdion-präpolymer, reaktand und azolat
EP19711129.7A Pending EP3768751A1 (de) 2018-03-23 2019-03-21 Wässrige uretdiongruppenhaltige zusammensetzungen und verfahren zu deren herstellung
EP19711126.3A Pending EP3768750A1 (de) 2018-03-23 2019-03-21 Wässrige uretdiongruppenhaltige zusammensetzungen und verfahren zu deren herstellung
EP19713667.4A Withdrawn EP3768755A1 (de) 2018-03-23 2019-03-21 Zusammensetzungen mit polyuretdionharzen
EP19711127.1A Withdrawn EP3768748A1 (de) 2018-03-23 2019-03-21 Katalysatorsystem für uretdiondispersionen

Family Applications After (4)

Application Number Title Priority Date Filing Date
EP19713665.8A Withdrawn EP3768753A1 (de) 2018-03-23 2019-03-21 Verbesserte härtung für polyallophanatzusammensetzungen durch säureneutralisierung der grundierung
EP19713666.6A Withdrawn EP3768754A1 (de) 2018-03-23 2019-03-21 Polyuretdionhaltige harzmischungszusammensetzungen
EP19714972.7A Withdrawn EP3768759A1 (de) 2018-03-23 2019-03-21 Verlängerte topfzeit für niedrigtemperaturhärtende polyuretdionharze
EP19711125.5A Pending EP3768749A1 (de) 2018-03-23 2019-03-21 Wässrige uretdiongruppenhaltige zusammensetzungen und verfahren zu deren herstellung

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Country Link
EP (14) EP3768752A1 (de)
CN (10) CN111886271A (de)
WO (15) WO2019183330A1 (de)

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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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WO2019183304A1 (en) 2019-09-26
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EP3768751A1 (de) 2021-01-27
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CN111886271A (zh) 2020-11-03
WO2019183330A1 (en) 2019-09-26
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CN112105666B (zh) 2023-05-23
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EP3768755A1 (de) 2021-01-27
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