WO2019183323A1 - Formulations de polyuréthane/allophanate à un seul composant comprenant un réducteur réactif - Google Patents

Formulations de polyuréthane/allophanate à un seul composant comprenant un réducteur réactif Download PDF

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Publication number
WO2019183323A1
WO2019183323A1 PCT/US2019/023325 US2019023325W WO2019183323A1 WO 2019183323 A1 WO2019183323 A1 WO 2019183323A1 US 2019023325 W US2019023325 W US 2019023325W WO 2019183323 A1 WO2019183323 A1 WO 2019183323A1
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WO
WIPO (PCT)
Prior art keywords
diisocyanate
methyl
polyol
acetate
isocyanato
Prior art date
Application number
PCT/US2019/023325
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English (en)
Inventor
Alan Ekin
Joseph Pierce
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 US15/933,507 external-priority patent/US20190292294A1/en
Priority claimed from EP18163625.9A external-priority patent/EP3543271A1/fr
Priority claimed from US15/933,527 external-priority patent/US20190292296A1/en
Priority claimed from US15/933,470 external-priority patent/US11292864B2/en
Priority claimed from US15/933,500 external-priority patent/US10696775B2/en
Priority claimed from EP18163621.8A external-priority patent/EP3543270A1/fr
Priority claimed from US15/933,553 external-priority patent/US10633477B2/en
Priority claimed from US15/933,475 external-priority patent/US11008416B2/en
Priority claimed from US15/933,570 external-priority patent/US10731051B2/en
Priority claimed from US15/933,487 external-priority patent/US20190292305A1/en
Priority claimed from US15/933,495 external-priority patent/US11312881B2/en
Priority claimed from EP18163620.0A external-priority patent/EP3543269A1/fr
Priority claimed from US15/933,511 external-priority patent/US11440988B2/en
Priority claimed from EP18181876.6A external-priority patent/EP3590987A1/fr
Priority claimed from EP18181877.4A external-priority patent/EP3590988A1/fr
Priority to EP19713670.8A priority Critical patent/EP3768758A1/fr
Application filed by Covestro Llc, Covestro Deutschland Ag filed Critical Covestro Llc
Publication of WO2019183323A1 publication Critical patent/WO2019183323A1/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
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/10—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
    • 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
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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
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    • C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
    • C08G18/20—Heterocyclic amines; Salts thereof
    • C08G18/2045—Heterocyclic amines; Salts thereof containing condensed heterocyclic rings
    • C08G18/2063—Heterocyclic amines; Salts thereof containing condensed heterocyclic rings having two nitrogen atoms in the condensed ring system
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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    • C08G18/20—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
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    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
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    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/2805—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
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    • C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
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    • C—CHEMISTRY; METALLURGY
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    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
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    • C08G18/30—Low-molecular-weight compounds
    • 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
    • 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
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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
    • C08G18/40—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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    • C08G18/72—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
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    • 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
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    • 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
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    • C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
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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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    • C08G18/7837—Nitrogen containing -N-C=0 groups containing ureum or ureum derivative groups containing allophanate 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
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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
    • C09D175/04—Polyurethanes
    • C09D175/06—Polyurethanes from polyesters
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    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
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    • C09D175/12—Polyurethanes from compounds containing nitrogen and active hydrogen, the nitrogen atom not being part of an isocyanate group
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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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    • 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
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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 one component, polyurethane/allophanate clear-coat compositions used in conjunction with a basecoat and a reactive reducer.
  • the reactive reducer contains a tertiary amine catalyst for a possible dual role of catalyzing the clear-coat and neutralizing the basecoat, if necessary.
  • the present invention attempts to alleviate problems inherent in the art by providing an alternative cross-linking approach to obtain compositions having physical properties similar to those of polyurethane compositions.
  • Various embodiments of the inventive approach involve crosslinking polyuretdione resins with neutralized polyols in the presence of a reactive reducer containing a reducing agent and a tertiary amine catalyst. The reaction between the polyol and the
  • compositions and methods are described in terms of “comprising” various components or steps, the compositions and methods can also“consist essentially of” or“consist of” the various components or steps.
  • adheresive or “adhesive compound” refer to any substance that can adhere or bond two items together. Implicit in the definition of an "adhesive composition” or “adhesive formulation” is the concept that the composition or formulation is a combination or mixture of more than one species, component or compound, which can include adhesive monomers, oligomers, and polymers along with other materials.
  • A“sealant composition” refers to a composition which may be applied to one or more surfaces to form a protective barrier, for example to prevent ingress or egress of solid, liquid or gaseous material or alternatively to allow selective permeability through the barrier to gas and liquid. In particular, it may provide a seal between surfaces.
  • A“casting composition” refers to a mixture of liquid chemical components which is usually poured into a mold containing a hollow cavity of the desired shape, and then allowed to solidify.
  • 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,
  • 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
  • 1 ,6-hexamethylene diisocyanate (HDI), 2,2,4-trimethyl-1 ,6-hexamethylene diisocyanate, 1 ,12-dodecamethylene diisocyanate, cyclohexane-1 ,3- and 1 ,4-diisocyanate, 1 -isocyanato-2-isocyanato-methyl cyclopentane, 1 - isocyanato-3-isocyanatomethyl-3, 5, 5-trimethyl cyclohexane (isophorone diisocyanate or IPDI), bis-(4-isocyanatocyclohexyl)methane, 1 ,3- and 1 ,4- bis(isocyanatomethyl)-cyclohexane, bis-(4-isocyanato-3-methyl- cyclohexyl)-methane, a,a,a',a'-tetramethyl-1 ,3- and 1 ,4-xylene
  • diisocyanate 1 -isocyanato-1 -methyl-4(3)-isocyanato-methyl cyclohexane, and 2,4- and 2,6-hexahydrotoluene diisocyanate, toluene diisocyanate (TDI), diphenylmethane diisocyanate (MDI), pentane diisocyanate (PDI) - bio-based, and, isomers of any of these; or combinations of any of these. Mixtures of diisocyanates may also be used.
  • Preferred diisocyanates include 1 ,6-hexamethylene diisocyanate, isophorone diisocyanate, and bis(4-isocyanatocyclohexyl)-methane because they are readily available and yield relatively low viscosity polyuretdione polyurethane oligomers.
  • the polyols useful in the present invention may be either low molecular weight (65-399 Da, as determined by gel permeation
  • the polyol of the present invention includes low molecular weight diols, triols and higher alcohols and polymeric polyols such as polyester polyols, polyether polyols, polycarbonate polyols, polyurethane polyols and hydroxy-containing (meth)acrylic polymers.
  • triols and higher alcohols include trimethylol propane and pentaerythritol. Also useful are polyols containing ether linkages such as diethylene glycol and triethylene glycol.
  • the suitable polyols are polymeric polyols having hydroxyl values less than 200, such as 10 to 180. Examples of polymeric polyols include polyalkylene ether polyols, polyester polyols including hydroxyl-containing polycaprolactones, hydroxy-containing (meth)acrylic polymers, polycarbonate polyols and polyurethane polymers.
  • polyether polyols examples include poly(oxytetramethylene) glycols, poly(oxyethylene) glycols, and the reaction product of ethylene glycol with a mixture of propylene oxide and ethylene oxide.
  • polyether polyols formed from the oxyalkylation of various polyols, for example, glycols such as ethylene glycol, 1 ,4-butane glycol, 1 ,6-hexanediol, and the like, or higher polyols, such as trimethylol propane, pentaerythritol and the like.
  • glycols such as ethylene glycol, 1 ,4-butane glycol, 1 ,6-hexanediol, and the like
  • polyols such as trimethylol propane, pentaerythritol and the like.
  • alkylene oxide for example, ethylene oxide in the presence of an acidic or basic catalyst.
  • Polyester polyols can also be used as a polymeric polyol component in the certain embodiments of the invention.
  • the polyester polyols can be prepared by the polyesterification of organic polycarboxylic acids or anhydrides thereof with organic polyols.
  • the polyester polyols Preferably, the
  • polycarboxylic acids and polyols are aliphatic or aromatic dibasic acids and diols.
  • the diols which may be employed in making the polyester include alkylene glycols, such as ethylene glycol and butylene glycol, neopentyl glycol and other glycols such as cyclohexane dimethanol, caprolactone diol (for example, the reaction product of caprolactone and ethylene glycol), polyether glycols, for example, poly(oxytetramethylene) glycol and the like.
  • alkylene glycols such as ethylene glycol and butylene glycol
  • neopentyl glycol and other glycols such as cyclohexane dimethanol
  • caprolactone diol for example, the reaction product of caprolactone and ethylene glycol
  • polyether glycols for example, poly(oxytetramethylene) glycol and the like.
  • other diols of various types and, as indicated, polyols of higher functionality may also be utilized in various embodiments of the invention.
  • Such higher polyols can include, for example, trimethylol propane, trimethylol ethane, pentaerythritol, and the like, as well as higher molecular weight polyols such as those produced by oxyalkylating low molecular weight polyols.
  • An example of such high molecular weight polyol is the reaction product of 20 moles of ethylene oxide per mole of trimethylol propane.
  • the acid component of the polyester consists primarily of monomeric carboxylic acids or anhydrides having 2 to 18 carbon atoms per molecule.
  • the acids which are useful are phthalic acid, isophthalic acid, terephthalic acid, tetrahydrophthalic acid, hexahydrophthalic acid, adipic acid, azelaic acid, sebacic acid, maleic acid, glutaric acid, chlorendic acid, tetrachlorophthalic acid and other dicarboxylic acids of varying types.
  • polycarboxylic acids such as trimellitic acid and tricarballylic acid (propane-1 ,2,3-tricarboxylic acid).
  • hydroxy- containing (meth)acrylic polymers or (meth)acrylic polyols can be used as the polyol component.
  • the (meth)acrylic polymers are polymers of 2 to 20 percent by weight primary hydroxy-containing vinyl monomers such as hydroxyalkyl acrylate and methacrylate having 2 to 6 carbon atoms in the alkyl group and 80 to 98 percent by weight of other ethylenically
  • alkyl(meth)acrylates unsaturated copolymerizable materials
  • alkyl(meth)acrylates unsaturated copolymerizable materials
  • the percentages by weight being based on the total weight of the monomeric charge.
  • suitable hydroxy alkyl(meth)acrylates are hydroxy ethyl and hydroxy butyl(meth)acrylate.
  • suitable alkyl acrylates and (meth)acrylates are lauryl methacrylate, 2-ethylhexyl methacrylate and n-butyl acrylate.
  • copolymerizable monomers which can be copolymerized with the hydroxyalkyl (meth)acrylates include ethylenically unsaturated materials such as monoolefinic and diolefinic hydrocarbons, halogenated
  • the polyol may be a polyurethane polyol.
  • These polyols can be prepared by reacting any of the above-mentioned polyols with a minor amount of polyisocyanate (OH/NCO equivalent ratio greater than 1 :1 ) so that free primary hydroxyl groups are present in the product.
  • polyisocyanate OH/NCO equivalent ratio greater than 1 :1
  • mixtures of both high molecular weight and low molecular weight polyols such as those mentioned above may be used.
  • Suitable hydroxy-functional polycarbonate polyols may be those prepared by reacting monomeric diols (such as 1 ,4-butanediol, 1 ,6- hexanediol, di-, tri- or tetraethylene glycol, di-, tri- or tetrapropylene glycol, 3-methyl-1 ,5-pentanediol, 4,4'-dimethylolcyclohexane and mixtures thereof) with diaryl carbonates (such as diphenyl carbonate, dialkyl carbonates (such as dimethyl carbonate and diethyl carbonate), alkylene carbonates (such as ethylene carbonate or propylene carbonate), or phosgene.
  • monomeric diols such as 1 ,4-butanediol, 1 ,6- hexanediol, di-, tri- or tetraethylene glycol, di-, tri- or tetrapropylene glycol, 3-methyl
  • the polyol is N-(2-aminoethyl)-2-aminoethyl
  • Acid scavengers should be covalently bonded to the acidic groups within the polyol.
  • Acid scavengers may be selected from carbodiimides, anhydrides, epoxies, trialkylorthoformates, amine compounds, or oxazolines. The present inventors believe, without wishing to be bound to any specific theory, that these acid scavengers covalently bind to carboxylic and acrylic acid groups within the polyols.
  • the clear-coat composition of the invention may be contacted with the basecoat by any methods known to those skilled in the art, including but not limited to, spraying, dipping, flow coating, rolling, brushing, pouring, and the like.
  • the clear-coat compositions may be applied in the form of paints or lacquers onto any compatible substrate, such as, for example, metals, plastics, ceramics, glass, and natural materials.
  • the clear-coat composition is applied as a single layer. In other embodiments, it may be applied as multiple layers as needed.
  • the reaction between the polyol and the polyuretdione will proceed once the reactive reducer has reduced the viscosity of the formulation to appropriate levels.
  • clear-coat curing is improved as the reactive reducer reduces the viscosity of the basecoat and at the same time neutralizes the basecoat, if necessary.
  • the basecoat does not require a neutralizer, the presence of tertiary amine in the basecoat can help with clear-coat curing by migrating to the clear-coat.
  • ADDITIVE B a surface additive on polyacrylate-basis for solvent-borne coating systems and printing inks, commercially available from BYK Chemie as BYK 358N;
  • URETDIONE A a 1 -isocyanato-3-isocyanatomethyl-3, 5,5- trimethyl cyclohexane (isophorone diisocyanate or IPDI)-based uretdione, commercially available from Covestro as CRELAN EF 403; REDUCER A a universal medium reducer, commercially
  • BASECOAT B 100 parts BASECOAT A and 50 parts
  • REACTIVE REDUCER B was added to both BASECOAT B and CLEAR-COAT A just before spray application.
  • the thickness of the black polyester BASECOAT A was 2 mils (50 pm) wet and the thickness of CLEAR-COAT A was 5 mils (125 pm) wet (2 mils (50 pm) dry).
  • the resulting panels were tested for microhardness and MEK double rubs and the results are summarized in Table I.
  • Films were cured at room temperature (21 O - 240) for one day, three days, one week, three weeks, and five weeks before testing.
  • REACTIVE REDUCER B was prepared using REDUCER A and catalyst.
  • Formulation A did not contain any catalyst; therefore, it was a control formulation for both basecoat and clear-coat.
  • Formulations B, C, and D contained increasing levels of catalyst.
  • Formulation A had very poor performance in terms of microhardness and MEK double rubs.
  • the performance of coating increased as the amount of catalyst in REACTIVE REDUCER B was increased (Formulations B through D).
  • Formulations B and C had enough levels of catalyst for clear-coat; however, not enough catalyst to act as a neutralizer for basecoat.
  • Formulation D had enough amount of catalyst to catalyze clear-coat and to neutralize basecoat.
  • the present inventors postulate that the catalyst may play a dual role; a) to catalyze clear-coat and b) to neutralize the acidic basecoat.
  • Table II summarizes the viscosities of Formulation A (clear-coat only) and establishes its storage stability.
  • the one component clear-coat had all the components mixed except the catalyst.
  • the inventive formulation can be supplied as one component, it was stored at room temperature for 14 months. It is apparent to those skilled in the art that the viscosity of the formulation showed no signs of viscosity increase over that time, thus demonstrating that the inventive coating can be stored as one component for an extended time.
  • the one component allophanate polymers produced by the present invention are believed to be particularly applicable for coatings, adhesives, castings, composites, and sealants.
  • a clear-coat composition comprising: a neutralized polyol; a polyuretdione resin; and a reactive reducer comprising a reducing agent and a tertiary amine catalyst.
  • cyclohexane isophorone diisocyanate or IPDI
  • IPDI isophorone diisocyanate
  • bis-(4- isocyanatocyclohexyl)methane 1 ,3- and 1 ,4-bis(isocyanatomethyl)- cyclohexane, bis-(4-isocyanato-3-methyl-cyclohexyl)-methane, a,a,a',a'- tetram ethyl -1 ,3- and 1 ,4-xylene diisocyanate, 1 -isocyanato-1 -methyl-4(3)- isocyanato-methyl cyclohexane, and 2,4- and 2,6-hexahydrotoluene diisocyanate, toluene diisocyanate (TDI), diphenylmethane diisocyanate (MDI), pentane diisocyanate (PDI) - bio-
  • the reactive reducer contains one selected from the group consisting of 1 ,8-diazabicyclo[5.4.0]undec-7-ene, 7-methyl-1 ,5,7- triazabicyclo[4.4.0]dec-5-ene, 1 ,4,5,6-tetrahydro-1 ,2-dimethylpyrimidine,
  • 1 1 A method of applying the clear-coat composition made according to one of clauses 1 to 10 to a substrate, wherein the method comprises at least one of spraying, dipping, flow coating, rolling, brushing, and pouring.
  • a one component composition comprising: a neutralized polyol; a polyuretdione resin; and a reducing agent, wherein the
  • composition has a storage stability of at least 14 months, as measured by viscosity increase.
  • a method of making a clear-coat composition comprising: combining a polyuretdione resin and a neutralized polyol in the presence of a reactive reducer comprising a reducing agent and a tertiary amine catalyst.
  • polyol is selected from the group consisting of polyalkylene ether polyols, polyester polyols, hydroxyl containing polycaprolactones, hydroxyl-containing (meth)acrylic polymers, polycarbonate polyols, polyurethane polyols, and combinations thereof.
  • polyuretdione resin comprises the reaction product of catalytic dimerization of an isocyanate.
  • TDI toluene diisocyanate
  • MDI diphenylmethane diisocyanate
  • PDI pentane diisocyanate
  • the reactive reducer contains one selected from the group consisting of 1 ,8- diazabicyclo[5.4.0]undec-7-ene, 7-methyl-1 ,5,7-triazabicyclo[4.4.0]dec-5- ene, 1 ,4,5,6-tetrahydro-1 ,2-dimethylpyrimidine, 1 ,2,4-triazole, sodium derivative and 2-tert-butyl-1 ,1 ,3,3-tetramethylguanidine, and combinations thereof.
  • An allophanate polymer system made by a method comprising: combining a neutralized polyol with a polyuretdione resin in the presence of a reactive reducer comprising a reducing agent and a tertiary amine catalyst to produce a clear-coat, and contacting the clear-coat with a basecoat comprising a reactive reducer which is the same as or different from the reactive reducer in the clear-coat.
  • an additive package selected from the group consisting of flow control additives, wetting agents, and a solvent.
  • polyuretdione resin comprises the reaction product of catalytic dimerization of an isocyanate.
  • the reducing agent is selected from the group consisting of n-butyl acetate, ethyl acetate, 2-methoxy-1 -methylethyl acetate, 1 - methoxy-2-propyl acetate, 2-methoxy-1 -propyl acetate, 2-ethoxyethyl acetate, n-heptane, methylcyclohexane, toluene, acetone, VM&P naphtha, naphtha, light aliphatic solvent naphtha, acetate, isobutyl acetate, mixed xylenes, ethylbenzene, methyl ethyl ketone, dimethyl ketone, methyl n-amyl ketone, methyl isobutyl ketone, 1 ,2,4 trimethyl benzene, isopropylbenzene, ethyl benzene, 1 -chloro-4 (trif
  • the contacting comprises at least one of spraying, dipping, flow coating, rolling, brushing, and pouring.

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Abstract

La présente invention concerne un système polymère d'allophanate fabriqué par un procédé comprenant la combinaison d'un polyol neutralisé avec une résine de polyuretdione en présence d'un réducteur réactif comprenant un agent réducteur et un catalyseur amine tertiaire pour produire une couche transparente et la mise en contact de la couche transparente avec une couche de base comprenant un catalyseur amine tertiaire. La réaction entre le polyol et la polyuretdione se déroulera après que le réducteur réactif a réduit la viscosité de la formulation de couche transparente à un seul composant à des niveaux appropriés. Le système polymère d'allophanate selon l'invention est particulièrement applicable pour obtenir des revêtements, des adhésifs, des moulages par coulée, des composites et des produits d'étanchéité ayant de bonnes performances.
PCT/US2019/023325 2018-03-23 2019-03-21 Formulations de polyuréthane/allophanate à un seul composant comprenant un réducteur réactif WO2019183323A1 (fr)

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US15/933,495 2018-03-23
US15/933,495 US11312881B2 (en) 2018-03-23 2018-03-23 One component polyurethane/allophanate formulations with reactive reducer
US15/933,500 US10696775B2 (en) 2018-03-23 2018-03-23 Curing for polyallophanate compositions through undercoat acid neutralization
US15/933,553 2018-03-23
US15/933,487 2018-03-23
EP18163620.0 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
US15/933,553 US10633477B2 (en) 2018-03-23 2018-03-23 Extended pot-life for low temperature curing polyuretdione resins
US15/933,475 US11008416B2 (en) 2018-03-23 2018-03-23 Aqueous, curable composition, comprising dispersed uretdione prepolymer, reactant and azolate
US15/933,507 US20190292294A1 (en) 2018-03-23 2018-03-23 One component allophanate formulations through basecoat catalyst migration
US15/933,500 2018-03-23
US15/933,570 2018-03-23
EP18163625.9 2018-03-23
US15/933,527 US20190292296A1 (en) 2018-03-23 2018-03-23 Polyol acid neutralization for low temperature uretdione curing
US15/933,475 2018-03-23
US15/933,470 US11292864B2 (en) 2018-03-23 2018-03-23 Compositions using polyuretdione resins
EP18163620.0A EP3543269A1 (fr) 2018-03-23 2018-03-23 Dispersions de polyuréthane contenant de l'uretdione comprenant des groupes hydrophiles
US15/933,511 US11440988B2 (en) 2018-03-23 2018-03-23 Polyuretdione-containing resin blend compositions
EP18163625.9A EP3543271A1 (fr) 2018-03-23 2018-03-23 Compositions aqueuses contenant des groupes urétdione et son procede de fabrication
US15/933,487 US20190292305A1 (en) 2018-03-23 2018-03-23 Uretdione based polyurethane compositions
EP18163621.8 2018-03-23
US15/933,527 2018-03-23
US15/933,507 2018-03-23
US15/933,570 US10731051B2 (en) 2018-03-23 2018-03-23 Basecoat acid neutralization through inorganic salts
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
EP18181876.6A EP3590987A1 (fr) 2018-07-05 2018-07-05 Compositions aqueuses contenant des groupes urétdione et leur procédé de production
EP18181877.4 2018-07-05
US15/933,511 2018-08-23

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PCT/US2019/023314 WO2019183315A1 (fr) 2018-03-23 2019-03-21 Neutralisation d'acide polyol pour durcissement d'urétdione à basse température
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/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/US2019/023297 WO2019183307A1 (fr) 2018-03-23 2019-03-21 Compositions de mélange de résines contenant des polyuretdione
PCT/EP2019/057065 WO2019180128A1 (fr) 2018-03-23 2019-03-21 Compositions aqueuses contenant des groupes uretdione et leur procédé de préparation
PCT/US2019/023334 WO2019183330A1 (fr) 2018-03-23 2019-03-21 Neutralisation d'acide de couche de fond au moyen de sels inorganiques
PCT/US2019/023299 WO2019183308A1 (fr) 2018-03-23 2019-03-21 Compositions utilisant des résines polyurétdione
PCT/US2019/023290 WO2019183304A1 (fr) 2018-03-23 2019-03-21 Compositions de polyuréthane à base 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/EP2019/057069 WO2019180131A1 (fr) 2018-03-23 2019-03-21 Compositions aqueuses contenant des groupes uretdione et procédé pour leur préparation
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
PCT/EP2019/057066 WO2019180129A1 (fr) 2018-03-23 2019-03-21 Système catalytique pour dispersions d'uretdione
PCT/EP2019/057064 WO2019180127A1 (fr) 2018-03-23 2019-03-21 Compositions aqueuses contenant des groupes uretdione et leur procédé de préparation
PCT/US2019/023325 WO2019183323A1 (fr) 2018-03-23 2019-03-21 Formulations de polyuréthane/allophanate à un seul composant comprenant un réducteur réactif

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PCT/US2019/023314 WO2019183315A1 (fr) 2018-03-23 2019-03-21 Neutralisation d'acide polyol pour durcissement d'urétdione à basse température
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/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/US2019/023297 WO2019183307A1 (fr) 2018-03-23 2019-03-21 Compositions de mélange de résines contenant des polyuretdione
PCT/EP2019/057065 WO2019180128A1 (fr) 2018-03-23 2019-03-21 Compositions aqueuses contenant des groupes uretdione et leur procédé de préparation
PCT/US2019/023334 WO2019183330A1 (fr) 2018-03-23 2019-03-21 Neutralisation d'acide de couche de fond au moyen de sels inorganiques
PCT/US2019/023299 WO2019183308A1 (fr) 2018-03-23 2019-03-21 Compositions utilisant des résines polyurétdione
PCT/US2019/023290 WO2019183304A1 (fr) 2018-03-23 2019-03-21 Compositions de polyuréthane à base 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/EP2019/057069 WO2019180131A1 (fr) 2018-03-23 2019-03-21 Compositions aqueuses contenant des groupes uretdione et procédé pour leur préparation
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
PCT/EP2019/057066 WO2019180129A1 (fr) 2018-03-23 2019-03-21 Système catalytique pour dispersions d'uretdione
PCT/EP2019/057064 WO2019180127A1 (fr) 2018-03-23 2019-03-21 Compositions aqueuses contenant des groupes uretdione et leur procédé de préparation

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