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WO2019183330A1 - Neutralisation d'acide de couche de fond au moyen de sels inorganiques - Google Patents

Neutralisation d'acide de couche de fond au moyen de sels inorganiques Download PDF

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Publication number
WO2019183330A1
WO2019183330A1 PCT/US2019/023334 US2019023334W WO2019183330A1 WO 2019183330 A1 WO2019183330 A1 WO 2019183330A1 US 2019023334 W US2019023334 W US 2019023334W WO 2019183330 A1 WO2019183330 A1 WO 2019183330A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
diisocyanate
pigments
methyl
pigment
Prior art date
Application number
PCT/US2019/023334
Other languages
English (en)
Inventor
Alan Ekin
Alan D. Bushmire
Original Assignee
Covestro Llc
Covestro Deutschland Ag
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 US15/933,500 external-priority patent/US10696775B2/en
Priority claimed from US15/933,553 external-priority patent/US10633477B2/en
Priority claimed from US15/933,511 external-priority patent/US11440988B2/en
Priority claimed from EP18163625.9A external-priority patent/EP3543271A1/fr
Priority claimed from US15/933,570 external-priority patent/US10731051B2/en
Priority claimed from US15/933,507 external-priority patent/US20190292294A1/en
Priority claimed from US15/933,495 external-priority patent/US11312881B2/en
Priority claimed from US15/933,487 external-priority patent/US20190292305A1/en
Priority claimed from EP18163621.8A external-priority patent/EP3543270A1/fr
Priority claimed from US15/933,527 external-priority patent/US20190292296A1/en
Priority claimed from EP18163620.0A external-priority patent/EP3543269A1/fr
Priority claimed from US15/933,475 external-priority patent/US11008416B2/en
Priority claimed from US15/933,470 external-priority patent/US11292864B2/en
Priority claimed from EP18181877.4A external-priority patent/EP3590988A1/fr
Priority claimed from EP18181876.6A external-priority patent/EP3590987A1/fr
Priority to EP19713339.0A priority Critical patent/EP3768752A1/fr
Application filed by Covestro Llc, Covestro Deutschland Ag filed Critical Covestro Llc
Publication of WO2019183330A1 publication Critical patent/WO2019183330A1/fr

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    • 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
    • C08G18/70—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
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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
    • C08G18/10—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
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    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
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    • 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
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    • 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
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    • C08G18/2072—Heterocyclic amines; Salts thereof containing condensed heterocyclic rings having at least three nitrogen atoms in the condensed ring system
    • C—CHEMISTRY; METALLURGY
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    • 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
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    • C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
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    • C—CHEMISTRY; METALLURGY
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    • C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
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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
    • C08G18/28—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
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    • 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
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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
    • C08G18/30—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
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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
    • C08G18/30—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
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    • C08G18/3225—Polyamines
    • C08G18/3253—Polyamines being in latent form
    • C08G18/3256—Reaction products of polyamines with aldehydes or ketones
    • C—CHEMISTRY; METALLURGY
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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
    • C08G18/42—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
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    • C08G18/40—High-molecular-weight compounds
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    • 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
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    • 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
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    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/73—Polyisocyanates or polyisothiocyanates acyclic
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    • 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
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    • C08G18/7831—Nitrogen containing -N-C=0 groups containing ureum or ureum derivative groups containing biuret groups
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    • 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
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    • 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
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    • 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
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    • 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
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    • C—CHEMISTRY; METALLURGY
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    • C08G2190/00—Compositions for sealing or packing joints

Definitions

  • the present invention relates, in general to polymers, and more specifically, to polymers made with neutralized polyols, uretdiones and tertiary amine catalysts that cure over neutralized basecoats.
  • 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, of the polyol, and by the use of a blocking agent.
  • Uretdione-based clear coats face some challenges when applied over pigmented basecoats due to the acidic nature of the basecoats.
  • the present invention attempts to alleviate problems inherent in the art by providing such 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 tertiary amine catalyst over a neutralized basecoat.
  • the polyol may be neutralized by reaction with an epoxy or cabodiimide at a temperature ranging from room temperature (21 ⁇ -24 ⁇ ) to 120 ⁇ .
  • the resulting allophanate p olymer may be used to make coatings, adhesives, castings, composites, and sealants.
  • the basecoat may be neutralized by complex formation with an inorganic salt.
  • the uretdione-based clear-coating of the invention may be applied over neutralized basecoats.
  • 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 system comprising an allophanate composition comprising a neutralized polyol, a polyuretdione resin, a tertiary amine catalyst, an additive package, and a reducer; and a neutralized basecoat comprising an inorganic salt and a pigment.
  • the present invention further provides a method of making an allophanate system comprising combining a neutralized polyol with a polyuretdione resin in the presence of a tertiary amine catalyst, an additive package, and a reducer to produce an allophanate composition, and contacting the allophanate composition with a neutralized basecoat comprising an inorganic salt and a pigment.
  • the polyol may be neutralized with a carbodiimide or an epoxy acid scavenger at a temperature ranging from room temperature (21 °C -24 ⁇ ) to 120 ⁇ .
  • the basecoat may be neutralized with an inorganic salt through complex formation with acidic groups within the basecoat.
  • the present invention provides a method for producing an allophanate polymer over neutralized basecoats by the following route:
  • 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
  • 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 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 nonflowing 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-di methyl pyrazole, 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.
  • 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 (colorants). 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.
  • 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.
  • 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 (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 (n-BA).
  • 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-1 ,5
  • 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
  • Suitable epoxy or carbodiimide acid scavenging 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.
  • Glycidyl ethers such as 1 ,4-cyclohexanedimethanol diglycidyl ether, commercially available from Air Products as EPODIL 757 are also suitable in the practice of the present invention.
  • Inorganic salts should be complexed with the acidic groups within the basecoat.
  • the present inventors believe, without wishing to be bound to any specific theory, that these inorganic salts act as acid scavengers by complexing with the carboxylic and acrylic acid groups within the basecoat.
  • a preferred type of inorganic salt for use in various embodiments of the present invention contains a metal ion.
  • suitable metal ions for inclusion in the inorganic salts include, but are not limited to, titanium, vanadium, aluminum chromium, manganese, potassium, iron, cobalt, nickel, lithium, copper, zirconium, zinc, and the lanthanides (lanthanum, cerium, praseodymium, neodymium, promethium, samarium, europium, gadolinium, terbium, dysprosium, holmium, erbium, thulium, ytterbium, and lutetium).
  • Suitable inorganic salts for use in the present invention include, but are not limited to, metal acetylaceto nates such as zinc(ll)
  • acetylacetonate aluminum acetylacetonate, iron(lll) acetylacetonate, lithium acetylacetonate, nickel(ll) acetylacetonate, zirconium(IV) acetylacetonate, and potassium acetylacetonate.
  • the neutralization of the polyol and of the basecoat is conducted at any temperature ranging from room temperature (21 ⁇ -24 ⁇ ) to 120 ⁇ , in other embodim ents from room temperature (21 ⁇ -24 ⁇ ) to 80 * 0 and in certain emb odiments at room temperature (21 -24 ⁇ ).
  • 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,
  • Urethane reducers are available in slow, medium and fast formulations, and may improve atomization, flow and leveling, which provide a smooth finish with less "orange peel.” Depending on the“speed” of the reducer, it 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 ethyl ketone, dimethyl ketone,
  • the basecoats useful in the invention include one or more colorants, such as pigments and dyes.
  • Any suitable pigment can be used in the basecoat of the present invention.
  • suitable pigments include inorganic white pigments, inorganic chromatic pigments, iron oxide pigments, oxidic mixed-phase pigments, organic pigments, and inorganic black pigments.
  • inorganic white pigments mention should be made in particular of oxides, such as titanium dioxide, zinc oxide (ZnO, zinc white), zirconium oxide, carbonates such as lead white, sulfates, such as lead sulfate, and sulfides such as zinc sulfide, and lithopones; titanium dioxide is particularly preferred.
  • oxides such as titanium dioxide, zinc oxide (ZnO, zinc white), zirconium oxide, carbonates such as lead white, sulfates, such as lead sulfate, and sulfides such as zinc sulfide, and lithopones; titanium dioxide is particularly preferred.
  • inorganic chromatic pigments mention should be made of those from the group of oxides and hydroxides in the form of their individual inorganic compounds or mixed phases, especially iron oxide pigments, chromium oxide pigments and oxidic mixed-phase pigments with rutile or spinel structure, and also bismuth vanadate, cadmium, cerium sulfide, chromate, ultramarine and iron blue pigments.
  • iron oxide pigments are Color Index Pigment Yellow 42, Pigment Red 101 , Pigment Blue 1 1 , Pigment Brown 6, and transparent iron oxide pigments.
  • chromium oxide pigments are Color Index Pigment Green 17 and Pigment Green 18.
  • oxidic mixed-phase pigments are nickel titanium yellow and chromium titanium yellow, cobalt green and cobalt blue, zinc iron brown and chromium iron brown, and also iron manganese black and spinel black.
  • Examples of preferred organic pigments are those of the monoazo, disazo, laked azo, b-naphthol, Naphiol AS, benzimidazolone, disazo condensation, azo metal complex, isoindoline and isoindolinone series, and also polycyclic pigments such as those from the phthalocyanine, quinacridone, perylene, perinone, thioindigo,
  • laked dyes such as Ca, Mg and Al lakes of dyes containing sulfonic acid or carboxylic acid groups, and also carbon blacks, which for the purposes of this specification are taken to be pigments and of which a large number are known. Mention should be made in particular of acidic to alkaline carbon blacks obtained by the furnace black process, and also chemically surface-modified carbon blacks, examples being sulfo- or carboxyl-containing carbon blacks.
  • inorganic black pigments examples include those as already described above together with the inorganic chromatic pigments, especially black iron oxide, spinel black, and black oxidic mixed-phase pigments.
  • the basecoat can contain the pigment at a level of at least 1%, in some cases at least 2%, in other cases at least 5% by weight, in some situations at least 10% and in other situations at least 15% by weight. Also, the basecoat can contain the pigment at a level of up to 60%, in some cases up to 50%, in other cases up to 40%, in some situations up to 35% and in other situations up to 30% by weight, based on the weight of basecoat.
  • the amount of the pigment in the basecoat can be any of the values recited above or can range between any of the values recited above.
  • 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.
  • 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 composition of the invention is applied as a single layer. In other embodiments, the inventive composition may be applied as multiple layers as needed.
  • 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.
  • REDUCER A a universal medium reducer
  • 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 an IPDI based uretdione prepolymer, proprietary product of Covestro, having a uretdione equivalent weight of 1 ,276 and a viscosity of 817 cPs in 50% butyl acetate.
  • the BASECOAT formulations A, B, C, D, E, F, G, and H in Table I were prepared following the same procedure.
  • Five parts of respective ADDITIVE (C, D, E, F, G, H, I, and J) was mixed in with 100 parts of BASECOAT A and grinded using glass beads in a metal can by using a paint shaker. After grinding, 50 parts of REDUCER A and the resulting mixture was mixed in a 200 mL plastic container using a FLACKTEK speed mixer for one minute followed by application using a conventional HVLP spray.
  • the BASECOAT formulation I is a reference formulation that did not need to be mixed with any of the ADDITIVES C, D, E, F, G, H, I, and J.
  • Iron phosphate treated ACT B952, 4”x12” test panels were used. Thickness of basecoat was 2 mils (50 pm) wet and thickness of the one component coating was 5 mils (125 pm) wet (2 mils (50 pm) dry). The resulting panels were used to test for MEK double rubs.
  • MEK double rubs were measured according to ASTM D4752- 10(2015). Results reported are an average of three readings for each formulation.
  • One day (RT) is the test results of the coatings (basecoat, clear-coat) that were cured at room temperature for 1 day (no long term basecoat aging).
  • One day (100 1C) is the test resu Its of the coatings (basecoat, clear-coat) that were cured at 100 O fo r 30 minutes and resting at room temperature for 1 day before testing (no long term basecoat aging).
  • 6 weeks is the test results of the coatings that ADDITIVES C, D, E, F, G, H, I and J had been aged with BASECOAT A at room temperature for 6 weeks.
  • Example I is a reference formulation that did not receive any additives into BASECOAT A. All examples A, B, C, D, E, F, G, H, and I received the same clear-coat over basecoat. Looking at MEK double rubs results, it is apparent to those skilled in the art that neutralization of basecoat with the inorganic salt improves chemical resistance of clear-coat significantly.
  • a system comprising: an allophanate composition comprising a neutralized polyol, a polyuretdione resin, a tertiary amine catalyst, an additive package, and a reducer, and a neutralized basecoat comprising an inorganic salt and a pigment.
  • an allophanate composition comprising a neutralized polyol, a polyuretdione resin, a tertiary amine catalyst, an additive package, and a reducer, and a neutralized basecoat comprising an inorganic salt and a pigment.
  • tertiary amine is selected from the group consisting of 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.
  • 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.
  • the metal is selected from the group consisting of titanium, vanadium, aluminum chromium, manganese, potassium, iron, cobalt, nickel, lithium, copper, zirconium, zinc, lanthanum, cerium, praseodymium, neodymium, promethium, samarium, europium, gadolinium, terbium, dysprosium, holmium, erbium, thulium, ytterbium, and lutetium.
  • the metal is selected from the group consisting of titanium, vanadium, aluminum chromium, manganese, potassium, iron, cobalt, nickel, lithium, copper, zirconium, zinc, lanthanum, cerium, praseodymium, neodymium, promethium, samarium, europium, gadolinium, terbium, dysprosium, holmium, erbium, thulium, ytterbium, and lutet
  • the inorganic salt is selected from the group consisting of zinc(ll) acetylacetonate, aluminum acetylacetonate, iron(lll) acetylacetonate, lithium acetylacetonate, nickel(ll) acetylacetonate, zirconium(IV) acetylacetonate, and potassium
  • the pigment is selected from the group consisting of titanium dioxide, zinc oxide (ZnO), zirconium oxide, lead white, lead sulfate, zinc sulfide, and lithopones, titanium dioxide, bismuth vanadate, cadmium, cerium sulfide, chromate, ultramarine iron blue pigments, Color Index Pigment Yellow 42, Pigment Red 101 , Pigment Blue 11, Pigment Brown 6, transparent iron oxide pigments, Color Index Pigment Green 17, Pigment Green 18, nickel titanium yellow, chromium titanium yellow, cobalt green, cobalt blue, zinc iron brown, chromium iron brown, iron manganese black, spinel black, carbon black, and black iron oxide.
  • the pigment is selected from the group consisting of titanium dioxide, zinc oxide (ZnO), zirconium oxide, lead white, lead sulfate, zinc sulfide, and lithopones, titanium dioxide, bismuth vanadate, cadmium, cerium sulfide, chromate, ultramarine iron blue
  • TDI toluene diisocyanate
  • MDI diphenylmethane diisocyanate
  • PDI pentane diisocyanate
  • the method comprises at least one of spraying, dipping, flow coating, rolling, brushing, and pouring.
  • a method of making an allophanate system comprising: combining a neutralized polyol with a polyuretdione resin in the presence of a tertiary amine catalyst, an additive package, and a reducer to produce an allophanate composition, and contacting the allophanate composition with a neutralized basecoat comprising an inorganic salt and a pigment.
  • the tertiary amine catalyst comprises an amidine.
  • tertiary amine is selected from the group consisting of 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.
  • 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.
  • the metal is selected from the group consisting of titanium, vanadium, aluminum chromium, manganese, potassium, iron, cobalt, nickel, lithium, copper, zirconium, zinc, lanthanum, cerium, praseodymium, neodymium, promethium, samarium, europium, gadolinium, terbium, dysprosium, holmium, erbium, thulium, ytterbium, and lutetium.
  • the inorganic salt is selected from the group consisting of zinc(ll) acetylacetonate, aluminum acetylacetonate, iron(lll) acetylacetonate, lithium
  • the pigment is selected from the group consisting of titanium dioxide, zinc oxide (ZnO), zirconium oxide, lead white, lead sulfate, zinc sulfide, and lithopones, titanium dioxide, bismuth vanadate, cadmium, cerium sulfide, chromate, ultramarine iron blue pigments, Color Index Pigment Yellow 42, Pigment Red 101 , Pigment Blue 11, Pigment Brown 6, transparent iron oxide pigments, Color Index Pigment Green 17, Pigment Green 18, nickel titanium yellow, chromium titanium yellow, cobalt green, cobalt blue, zinc iron brown, chromium iron brown, iron manganese black, spinel black, carbon black, and black iron oxide.
  • the pigment is selected from the group consisting of titanium dioxide, zinc oxide (ZnO), zirconium oxide, lead white, lead sulfate, zinc sulfide, and lithopones, titanium dioxide, bismuth vanadate, cadmium, cerium sulfide, chromate, ultramarine iron blue
  • TDI toluene diisocyanate
  • MDI diphenylmethane diisocyanate
  • PDI pentane diisocyanate
  • [0109] 34 A method of applying the allophanate system made according to one of clauses 18 to 33 to a substrate, wherein the method 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)
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  • 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)
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Abstract

La présente invention concerne un système comprenant une composition d'allophanate comprenant un polyol neutralisé, une résine de polyuretdione, un catalyseur amine tertiaire, une combinaison d'additifs et un agent réducteur ; et une couche de fond neutralisée comprenant un sel inorganique et un pigment. La présente invention concerne en outre un procédé de production d'un système allophanate consistant à combiner un polyol neutralisé avec une résine de polyuretdione en présence d'un catalyseur amine tertiaire, d'une combinaison d'additifs, et d'un agent réducteur afin de produire une composition d'allophanate, et à mettre en contact la composition d'allophanate avec une couche de fond neutralisée comprenant un sel inorganique et un pigment. Le système peut être utilisé pour fabriquer des revêtements, des adhésifs, des moulages, des composites et des agents d'étanchéité dans lesquels un revêtement transparent sur des couches de fond pigmentées neutralisées est considérablement amélioré par rapport au revêtement sur des couches de fond non neutralisées.
PCT/US2019/023334 2018-03-23 2019-03-21 Neutralisation d'acide de couche de fond au moyen de sels inorganiques WO2019183330A1 (fr)

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EP18163620.0A EP3543269A1 (fr) 2018-03-23 2018-03-23 Dispersions de polyuréthane contenant de l'uretdione comprenant des groupes hydrophiles
US15/933,570 US10731051B2 (en) 2018-03-23 2018-03-23 Basecoat acid neutralization through inorganic salts
US15/933,553 2018-03-23
US15/933,507 US20190292294A1 (en) 2018-03-23 2018-03-23 One component allophanate formulations through basecoat catalyst migration
EP18163625.9 2018-03-23
US15/933,495 US11312881B2 (en) 2018-03-23 2018-03-23 One component polyurethane/allophanate formulations with reactive reducer
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
US15/933,500 2018-03-23
US15/933,511 US11440988B2 (en) 2018-03-23 2018-03-23 Polyuretdione-containing resin blend compositions
US15/933,475 2018-03-23
EP18163620.0 2018-03-23
EP18163625.9A EP3543271A1 (fr) 2018-03-23 2018-03-23 Compositions aqueuses contenant des groupes urétdione et son procede de fabrication
US15/933,475 US11008416B2 (en) 2018-03-23 2018-03-23 Aqueous, curable composition, comprising dispersed uretdione prepolymer, reactant and azolate
US15/933,487 2018-03-23
US15/933,507 2018-03-23
US15/933,511 2018-03-23
US15/933,470 US11292864B2 (en) 2018-03-23 2018-03-23 Compositions using polyuretdione resins
US15/933,553 US10633477B2 (en) 2018-03-23 2018-03-23 Extended pot-life for low temperature curing polyuretdione resins
US15/933,527 US20190292296A1 (en) 2018-03-23 2018-03-23 Polyol acid neutralization for low temperature uretdione curing
US15/933,495 2018-03-23
US15/933,527 2018-03-23
US15/933,570 2018-03-23
EP18163621.8 2018-03-23
EP18163621.8A EP3543270A1 (fr) 2018-03-23 2018-03-23 Système catalyseur pour dispersions d'uretdions
US15/933,470 2018-03-23
EP18181876.6A EP3590987A1 (fr) 2018-07-05 2018-07-05 Compositions aqueuses contenant des groupes urétdione et leur procédé de production
EP18181876.6 2018-07-05
EP18181877.4A EP3590988A1 (fr) 2018-07-05 2018-07-05 Compositions aqueuses contenant des groupes urétdione et leur procédé de production
EP18181877.4 2018-07-05

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PCT/US2019/023312 WO2019183313A1 (fr) 2018-03-23 2019-03-21 Durée de vie en pot prolongée pour des résines polyurétdione à durcissement à basse température
PCT/US2019/023297 WO2019183307A1 (fr) 2018-03-23 2019-03-21 Compositions de mélange de résines contenant des polyuretdione
PCT/US2019/023334 WO2019183330A1 (fr) 2018-03-23 2019-03-21 Neutralisation d'acide de couche de fond au moyen de sels inorganiques
PCT/EP2019/057064 WO2019180127A1 (fr) 2018-03-23 2019-03-21 Compositions aqueuses contenant des groupes uretdione et leur procédé de préparation
PCT/US2019/023290 WO2019183304A1 (fr) 2018-03-23 2019-03-21 Compositions de polyuréthane à base d'uretdione
PCT/US2019/023314 WO2019183315A1 (fr) 2018-03-23 2019-03-21 Neutralisation d'acide polyol pour durcissement d'urétdione à basse température
PCT/EP2019/057065 WO2019180128A1 (fr) 2018-03-23 2019-03-21 Compositions aqueuses contenant des groupes uretdione et leur procédé de préparation
PCT/US2019/023299 WO2019183308A1 (fr) 2018-03-23 2019-03-21 Compositions utilisant des résines polyurétdione
PCT/US2019/023319 WO2019183319A1 (fr) 2018-03-23 2019-03-21 Formulations d'allophanate à un composant par migration de catalyseur de couche de base
PCT/US2019/023292 WO2019183305A1 (fr) 2018-03-23 2019-03-21 Durcissement amélioré de compositions de polyallophanate par neutralisation de l'acide de sous-couche
PCT/EP2019/057069 WO2019180131A1 (fr) 2018-03-23 2019-03-21 Compositions aqueuses contenant des groupes uretdione et procédé pour leur préparation
PCT/EP2019/057066 WO2019180129A1 (fr) 2018-03-23 2019-03-21 Système catalytique pour dispersions d'uretdione
PCT/EP2019/057068 WO2019180130A1 (fr) 2018-03-23 2019-03-21 Dispersions de polyuréthane contenant de l'urétdione comprenant des groupes hydrophiles
PCT/US2019/023325 WO2019183323A1 (fr) 2018-03-23 2019-03-21 Formulations de polyuréthane/allophanate à un seul composant comprenant un réducteur réactif
PCT/US2019/023286 WO2019183300A1 (fr) 2018-03-23 2019-03-21 Composition aqueuse durcissable comprenant un prépolymère d'urétdione dispersé, un réactif et un azolate

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PCT/US2019/023290 WO2019183304A1 (fr) 2018-03-23 2019-03-21 Compositions de polyuréthane à base d'uretdione
PCT/US2019/023314 WO2019183315A1 (fr) 2018-03-23 2019-03-21 Neutralisation d'acide polyol pour durcissement d'urétdione à basse température
PCT/EP2019/057065 WO2019180128A1 (fr) 2018-03-23 2019-03-21 Compositions aqueuses contenant des groupes uretdione et leur procédé de préparation
PCT/US2019/023299 WO2019183308A1 (fr) 2018-03-23 2019-03-21 Compositions utilisant des résines polyurétdione
PCT/US2019/023319 WO2019183319A1 (fr) 2018-03-23 2019-03-21 Formulations d'allophanate à un composant par migration de catalyseur de couche de base
PCT/US2019/023292 WO2019183305A1 (fr) 2018-03-23 2019-03-21 Durcissement amélioré de compositions de polyallophanate par neutralisation de l'acide de sous-couche
PCT/EP2019/057069 WO2019180131A1 (fr) 2018-03-23 2019-03-21 Compositions aqueuses contenant des groupes uretdione et procédé pour leur préparation
PCT/EP2019/057066 WO2019180129A1 (fr) 2018-03-23 2019-03-21 Système catalytique pour dispersions d'uretdione
PCT/EP2019/057068 WO2019180130A1 (fr) 2018-03-23 2019-03-21 Dispersions de polyuréthane contenant de l'urétdione comprenant des groupes hydrophiles
PCT/US2019/023325 WO2019183323A1 (fr) 2018-03-23 2019-03-21 Formulations de polyuréthane/allophanate à un seul composant comprenant un réducteur réactif
PCT/US2019/023286 WO2019183300A1 (fr) 2018-03-23 2019-03-21 Composition aqueuse durcissable comprenant un prépolymère d'urétdione dispersé, un réactif et un azolate

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