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, in general to polymers, and more specifically, to polymers made with blended isocyanate-based uretdione- containing resins, neutralized polyols, and tertiary amine catalysts.
• the resulting allophanate polymers may be used to make coatings, adhesives, castings, composites, and sealants.
• 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 an 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.
• the present invention reduces or eliminates problems inherent in the art by providing a reaction mixture comprising a blend of a first isocyanate-based uretdione-containing resin and a second isocyanate-based uretdione-containing resin; a neutralized polyol and a tertiary amine catalyst; and optionally, an additive package selected from the group consisting of flow control additives, pigments (colorants), wetting agents, and solvents, wherein the first isocyanate and the second isocyanate are different.
• the first isocyanate-based uretdione-containing resin and the second isocyanate-based uretdione-containing resin may be cold blended or hot blended.
• Uretdione-containing resins can be crossl inked with polyols to form allophanate groups in the presence of tertiary amine catalysts.
• Uretdiones can be made by catalytic dimerization of isocyanates. After dimerization, the remaining isocyanates can be reacted with polyols (diols, monools) to increase functionality and/or molecular weight.
• polyols diols, monools
• Different isocyanate-based uretdione-containing resins can be made separately using polyols (diols, monools) in flasks, reactors, or vessels and later cold blended. The cold blended uretdione-containing resins can then be formulated with neutralized polyols and tertiary amine catalysts to provide optimum performance.
• hot blended uretdione-containing resins can be made by reacting two or more of different kinds of uretdione- containing resins in the same flasks, reactors, or vessels, and then reacting the remaining isocyanates with polyols (diols, monools).
• the hot blended uretdione-containing resins can be formulated with neutralized polyols and tertiary amine catalysts to provide optimum performance.
• the present inventors have unexpectedly discovered that coatings, adhesives, castings, composites, and sealants made from formulations that were made from hot blended uretdione containing resins exhibit superior performance over those formulations that were made from cold blended uretdione containing resins.
• any numerical range recited in this specification is intended to include all sub-ranges of the same numerical precision subsumed within the recited range.
• 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.
• the grammatical articles“a”,“an”, and“the”, as used herein, are intended to include“at least one” or“one or more”, unless otherwise indicated, even if“at least one” or“one or more” is expressly used in certain instances.
• these articles are used in this specification to refer to one or more than one (i.e., to“at least one”) of the grammatical objects of the article.
• “a component” means one or more components, and thus, possibly, more than one component is contemplated and may be employed or used in an implementation of the described embodiments.
• the use of a singular noun includes the plural, and the use of a plural noun includes the singular, unless the context of the usage requires otherwise.
• the present invention provides a reaction mixture comprising a blend of a first isocyanate-based uretdione- containing resin and a second isocyanate-based uretdione-containing resin; a neutralized polyol and a tertiary amine catalyst; and optionally, an additive package selected from the group consisting of flow control additives, pigments (colorants), wetting agents, and solvents, wherein the first isocyanate and the second isocyanate are different.
• the first isocyanate-based uretdione-containing resin and the second isocyanate-based uretdione-containing resin may be cold blended or hot blended. Coatings, adhesives, castings, composites, and sealants made from hot blended formulations exhibit superior performance over those made from cold blended formulations.
• the present invention further provides a method of making an allophanate polymer comprising blending a first isocyanate-based uretdione-containing resin and a second isocyanate-based uretdione-containing resin to form a resin blend, reacting the resin blend with a neutralized polyol in the presence of a tertiary amine catalyst, optionally in the presence of an additive package selected from the group consisting of flow control additives, pigments (colorants), wetting agents, and solvents, wherein the first isocyanate and the second isocyanate are different.
• the polyol may be neutralized by reaction with an acid scavenger at a temperature ranging from room temperature (21 ° - 24°) to 120°.
• an acid scavenger at a temperature ranging from room temperature (21 ° - 24°) to 120°.
• R1 and R2 are the same but different than R3 and R 4 .
• R3 and R 4 are the same but different than R1 and R2.
• Ri, R2, R3, and R 4 may be independently the same or different.
• the scheme shows the reaction with uretdione from R1 and R2 forming an allophanate group.
• the second uretdione from R 4 and R5 does form allophanate as well.
• the inventive allophanate polymer system is particularly applicable in 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
• the barrier 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 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.
• “hot blended” or “hot blending” means taking a first isocyanate-based uretdione-containing resin and a second isocyanate-based uretdione-containing resin and mixing them together in a flask, reactor, or other vessel, with heating while reacting with the appropriate polyol(s) to obtain a uretdione blend with specific functionality and molecular weight.
• the resulting hot blends may be liquid when cooled to room temperature after completion of the reaction.
• “cold blended” or“cold blending” means the first isocyanate-based uretdione-containing resin and the second isocyanate- based uretdione-containing resin are made in separate flasks, reactors, or other vessels, with the appropriate polyols to achieve a specific
• the resins After the completion of the reactions of uretdione-containing resins with polyols, the resins are cooled down to room temperature for cold blending. The first isocyanate-based uretdione- containing resin and the second isocyanate-based uretdione-containing resin are then mixed together at specified ratios. The resulting cold blends may be liquid.
• 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 112 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.
• organic diisocyanates which are suitable for the present invention include 1 ,4-tetramethylene diisocyanate, 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- cyclohexy
• diisocyanate 1 -isocyanato-1 -methyl-4(3)-isocyanato-methyl cyclohexane, and 2,4- and 2,6-hexahydrotoluene diisocyanate, toluene diisocyanate (TDI), diphenyl methane 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. Particularly preferred diisocyanates are 1 ,6-hexamethylene diisocyanate (HDI) and isophorone diisocyanate (IPDI).
• HDI 1 ,6-hexamethylene diisocyanate
• IPDI isophorone diisocyanate
• 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 reaction mixture containing the polyuretdione and the neutralized polyol in the presence of a tertiary amine catalyst may be heated to a temperature of 140°, in other embodiments to a temperature of fro m 20° to 140°.
• the polyols useful in the present invention may be either low molecular weight (62-399 Da, as determined by gel permeation
• the polyols in the present invention include 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 examples 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.
• 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.
• One commonly utilized oxyalkylation method is by reacting a polyol with an 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 polycarboxyl
• polycarboxyl ic 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.
• 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.
• polycarboxyl ic acids such as trimellitic acid and tricarballylic acid (where acids are referred to above, it is understood that the anhydrides of those acids which form anhydrides can be used in place of the acid).
• lower alkyl esters of acids such as dimethyl glutamate can be used.
• 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
• unsaturated copolymerizable materials such as alkyl(meth)acrylates; 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
• a minor amount of higher functional, monomeric polyols such as trimethylolpropane, glycerol or pentaerythritol, may be used.
• the polyol is N-(2-aminoethyl)-2-aminoethyl
• Acid scavengers should be covalently bonded to the acidic groups within the polyol.
• the acid scavengers may be selected from carbodiimides, anhydrides, epoxies, trialkylorthoformates, amine compounds, and 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
• the neutralization is conducted at any temperature ranging from room temperature (21 ° - 24° to 120°, in other embodiments from room temp erature (21 ° - 24°) to 80° and in certain embodiments at room te mperature (21 ° - 24°).
• the first and second isocyanate-based uretdione-containing resins may be blended (either hot blended or cold blended) at various ratios ranging from 92:8 to 24:76; in some embodiments the ratio may be 83:17 to 24:76; in yet other embodiments the ratio may be 74:26 and in still other embodiments the ratio may be 24:76 depending upon the identities of the first and second isocyanates.
• 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,
• compositions of the present invention may further include any of a variety of additives such as defoamers, devolatilizers, surfactants, thickeners, flow control additives, colorants (including pigments and dyes) or surface additives.
• additives such as defoamers, devolatilizers, surfactants, thickeners, flow control additives, colorants (including pigments and dyes) or surface additives.
• composition of the invention may be contacted with a substrate 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.
• inventive 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 inventive composition is applied as a single layer. In other embodiments, the composition of the present invention may be applied as multiple layers as needed.
• POLYOL A an aromatic free, branched hydroxyl-bearing polyester polyol, commercially available from Covestro LLC as DESMOPHEN 775 XP;
• ADDITIVE A an active anti-hydrolysis agent for polyester polyurethanes, being used as an acid scavenger for acidic groups within the polyols, commercially available from Rhein Chemie as STABAXOL I;
• ADDITIVE B a surface additive on polyacrylate-basis for solvent-borne coating systems and printing inks, commercially available from BYK Chemie as BYK 358N; CATALYST A 1 ,8-diazabicyclo[5.4.0]undec-7-ene (DBU), tertiary amine catalyst, commercially available from Air Products as POLYCAT DBU; 10% CATALYST A solution was made in butyl acetate;
• URETDIONE A a 1 -isocyanato-3-isocyanatomethyl-3, 5,5- trimethyl cyclohexane (isophorone diisocyanate or IPDI)-based uretdione prepolymer, proprietary product of Covestro LLC, having a uretdione equivalent weight of 1,276 and a viscosity of 817 cPs in 50% butyl acetate;
• URETDIONE B a 1 ,6-hexamethylene diisocyanate (HDI) and 1- isocyanato-3-isocyanatomethyl-3, 5, 5-trimethyl cyclohexane (isophorone diisocyanate or IPDI)- based uretdione prepolymer, proprietary product of Covestro LLC, having a uretdione equivalent weight of 824 and a viscosity of 8,250 cPs in 30% butyl acetate;
• HDI 1 ,6-hexamethylene diisocyanate
• IPDI isophorone diisocyanate
• URETDIONE C a 1 ,6-hexamethylene diisocyanate (HDI) and 1- isocyanato-3-isocyanatomethyl-3, 5, 5-trimethyl cyclohexane (isophorone diisocyanate or IPDI)- based uretdione prepolymer, proprietary product of Covestro LLC, having a uretdione equivalent weight of 822 and a viscosity of 16,500 cPs in 30% butyl acetate;
• HDI 1 ,6-hexamethylene diisocyanate
• IPDI isophorone diisocyanate
• URETDIONE D a 1 ,6-hexamethylene diisocyanate (HDI) and 1- isocyanato-3-isocyanatomethyl-3, 5, 5-trimethyl cyclohexane (isophorone diisocyanate or IPDI)- based uretdione prepolymer, proprietary product of Covestro LLC, having a uretdione equivalent weight of 820 and a viscosity of 15,300 cPs in 30% butyl acetate;
• HDI 1 ,6-hexamethylene diisocyanate
• IPDI isophorone diisocyanate
• URETDIONE E a 1 ,6-hexamethylene diisocyanate (HDI) and 1- isocyanato-3-isocyanatomethyl-3,5,5-trimethyl cyclohexane (isophorone diisocyanate or IPDI)- based uretdione prepolymer, proprietary product of Covestro LLC, having a uretdione equivalent weight of 814 and a viscosity of 8,680 cPs in 30% butyl acetate;
• HDI 1 ,6-hexamethylene diisocyanate
• IPDI isophorone diisocyanate
• URETDIONE F a 1 ,6-hexamethylene diisocyanate (HDI) and 1- isocyanato-3-isocyanatomethyl-3, 5, 5-trimethyl cyclohexane (isophorone diisocyanate or IPDI)- based uretdione prepolymer, proprietary product of Covestro LLC, having a uretdione equivalent weight of 812 and a viscosity of 22,500 cPs in 30% butyl acetate;
• HDI 1 ,6-hexamethylene diisocyanate
• IPDI isophorone diisocyanate
• URETDIONE G a 1 ,6-hexamethylene diisocyanate (HDI) and 1- isocyanato-3-isocyanatomethyl-3, 5, 5-trimethyl cyclohexane (isophorone diisocyanate or IPDI)- based uretdione prepolymer, proprietary product of Covestro LLC, having a uretdione equivalent weight of 808 and a viscosity of 12,900 cPs in 30% butyl acetate;
• HDI 1 ,6-hexamethylene diisocyanate
• IPDI isophorone diisocyanate
• URETDIONE H a 1 ,6-hexamethylene diisocyanate (HDI) and 1- isocyanato-3-isocyanatomethyl-3, 5, 5-trimethyl cyclohexane (isophorone diisocyanate or IPDI)- based uretdione prepolymer, proprietary product of Covestro LLC, having a uretdione equivalent weight of 809 and a viscosity of 9,220 cPs in 30% butyl acetate; URETDIONE I a 1 ,6-hexamethylene diisocyanate (HDI) and 1- isocyanato-3-isocyanatomethyl-3,5,5-trimethyl cyclohexane (isophorone diisocyanate or IPDI)- based uretdione prepolymer, proprietary product of Covestro LLC, having a uretdione equivalent weight of 808 and a viscosity of 18,800 cPs in 30% butyl
• URETDIONE J a 1 ,6-hexamethylene diisocyanate (HDI)-based uretdione prepolymer, proprietary product of Covestro LLC, having a uretdione equivalent weight of 871 and a viscosity of 10,800 cPs in 30% butyl acetate;
• HDI hexamethylene diisocyanate
• URETDIONE K a 1 ,6-hexamethylene diisocyanate (HDI)-based uretdione prepolymer, proprietary product of Covestro LLC, having a uretdione equivalent weight of 624 and a viscosity of 31 ,200 cPs in 20% butyl acetate.
• HDI hexamethylene diisocyanate
• Formulations A through AA in Table I were prepared following the same procedure. As an example, Formulation A was prepared as follows. POLYOL A had been reacted with ADDITIVE A prior to
• CATALYST A (10% solution in butyl acetate (n-BA)), 1 .70 parts n-butyl acetate, and 32.37 parts URETDIONE A were added. The resulting mixture was mixed using a FLACKTEK speed mixer for one minute followed by application using a drawdown bar.
• Zinc phosphate treated ACT B952, 3” x 9” (7.62 cm x 22.9) test panels were used. Thickness of coatings was 4 mils (100 pm) wet (2 mils (50 pm) dry). The resulting panels were used to test for MEK double rubs. [0062] Films were cured at 100 ° for 30 minutes and allow ed to stand for one day at room temperature before testing.
• MEK double rubs were measured according to ASTM D4752- 10(2015). Results reported are an average of three readings for each formulation.
• Examples A through AA were prepared to determine the difference between hot and cold blending of uretdione-containing resins on performance.
• Examples A, J, and K are reference formulations that were used for cold blending.
• Examples B, C, D, E, F, G, H, and I were hot blended formulations.
• Examples L, M, N, O, P, Q, R, S, T, U, V, W, X, Y, Z, and AA were cold blended formulations using Examples A, J, and K followed by coating formulation.
• Hot and cold blended formulations were made at the same blend ratios to permit direct comparison of their performance using MEK double rubs. By comparing the MEK double rubs results, it is apparent to those skilled in the art that coatings made from formulations containing resins that were hot blended had better performance (solvent resistance) based on MEK double rubs than corresponding coatings made from formulations containing cold blended resins.
• a reaction mixture comprising a blend of a first isocyanate- based uretdione-containing resin and a second isocyanate-based uretdione-containing resin; a neutralized polyol and a tertiary amine catalyst; and optionally, an additive package selected from the group consisting of flow control additives, pigments (colorants), wetting agents, and solvents, wherein the first isocyanate and the second isocyanate are different.
• TDI toluene diisocyanate
• MDI diphenyl methane diisocyanate
• PDI pentane diisocyanate
• a method of making an allophanate polymer comprising blending a first isocyanate-based uretdione-containing resin and a second isocyanate-based uretdione-containing resin to form a resin blend, reacting the resin blend with a neutralized polyol in the presence of a tertiary amine catalyst, optionally in the presence of an additive package selected from the group consisting of flow control additives, pigments (colorants), wetting agents, and solvents, wherein the first isocyanate and the second isocyanate are different.
• tertiary amine is 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.
• TDI toluene diisocyanate
• MDI diphenyl methane diisocyanate
• PDI pentane diisocyanate

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)

Applications Claiming Priority (16)

Publications (1)

Family

ID=65767037

Family Applications (14)

Family Applications Before (4)

Family Applications After (9)

Country Status (3)

Families Citing this family (3)

Family Cites Families (103)

• 2019
  • 2019-03-21 WO PCT/US2019/023319 patent/WO2019183319A1/en active Application Filing
  • 2019-03-21 CN CN201980034350.0A patent/CN112105666B/zh active Active
  • 2019-03-21 EP EP19713663.3A patent/EP3768747A1/de not_active Withdrawn
  • 2019-03-21 EP EP19711127.1A patent/EP3768748A1/de not_active Withdrawn
  • 2019-03-21 EP EP19714972.7A patent/EP3768759A1/de not_active Withdrawn
  • 2019-03-21 WO PCT/US2019/023299 patent/WO2019183308A1/en active Application Filing
  • 2019-03-21 WO PCT/EP2019/057065 patent/WO2019180128A1/de active Application Filing
  • 2019-03-21 CN CN201980021445.9A patent/CN111886272B/zh active Active
  • 2019-03-21 WO PCT/EP2019/057069 patent/WO2019180131A1/de active Application Filing
  • 2019-03-21 EP EP19713667.4A patent/EP3768755A1/de not_active Withdrawn
  • 2019-03-21 EP EP19713666.6A patent/EP3768754A1/de not_active Withdrawn
  • 2019-03-21 EP EP19713670.8A patent/EP3768758A1/de not_active Withdrawn
  • 2019-03-21 CN CN201980021506.1A patent/CN111868135A/zh active Pending
  • 2019-03-21 CN CN201980021447.8A patent/CN111886271A/zh active Pending
  • 2019-03-21 EP EP19713665.8A patent/EP3768753A1/de not_active Withdrawn
  • 2019-03-21 WO PCT/US2019/023297 patent/WO2019183307A1/en active Application Filing
  • 2019-03-21 CN CN201980021508.0A patent/CN112041367B/zh active Active
  • 2019-03-21 EP EP19711126.3A patent/EP3768750A1/de active Pending
  • 2019-03-21 WO PCT/US2019/023325 patent/WO2019183323A1/en active Application Filing
  • 2019-03-21 CN CN201980021559.3A patent/CN111868133A/zh active Pending
  • 2019-03-21 WO PCT/US2019/023290 patent/WO2019183304A1/en active Application Filing
  • 2019-03-21 EP EP19713668.2A patent/EP3768756A1/de active Pending
  • 2019-03-21 CN CN201980034098.3A patent/CN112105665A/zh active Pending
  • 2019-03-21 EP EP19711125.5A patent/EP3768749A1/de active Pending
  • 2019-03-21 WO PCT/US2019/023312 patent/WO2019183313A1/en active Application Filing
  • 2019-03-21 WO PCT/EP2019/057064 patent/WO2019180127A1/de active Application Filing
  • 2019-03-21 CN CN201980021448.2A patent/CN111886273A/zh active Pending
  • 2019-03-21 EP EP19711129.7A patent/EP3768751A1/de active Pending
  • 2019-03-21 EP EP19713339.0A patent/EP3768752A1/de active Pending
  • 2019-03-21 CN CN201980021630.8A patent/CN111868131A/zh active Pending
  • 2019-03-21 WO PCT/US2019/023292 patent/WO2019183305A1/en active Application Filing
  • 2019-03-21 CN CN201980021604.5A patent/CN112004853B/zh active Active
  • 2019-03-21 EP EP19713669.0A patent/EP3768757A1/de not_active Withdrawn
  • 2019-03-21 WO PCT/EP2019/057068 patent/WO2019180130A1/en active Application Filing
  • 2019-03-21 WO PCT/US2019/023286 patent/WO2019183300A1/en active Application Filing
  • 2019-03-21 WO PCT/EP2019/057066 patent/WO2019180129A1/de active Application Filing
  • 2019-03-21 EP EP19711128.9A patent/EP3768745A1/de not_active Withdrawn
  • 2019-03-21 WO PCT/US2019/023314 patent/WO2019183315A1/en active Application Filing
  • 2019-03-21 WO PCT/US2019/023334 patent/WO2019183330A1/en active Application Filing

Also Published As

Similar Documents

Legal Events