WO2019183315A1 - Neutralisation d'acide polyol pour durcissement d'urétdione à basse température - Google Patents

Neutralisation d'acide polyol pour durcissement d'urétdione à basse température Download PDF

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Publication number
WO2019183315A1
WO2019183315A1 PCT/US2019/023314 US2019023314W WO2019183315A1 WO 2019183315 A1 WO2019183315 A1 WO 2019183315A1 US 2019023314 W US2019023314 W US 2019023314W WO 2019183315 A1 WO2019183315 A1 WO 2019183315A1
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WO
WIPO (PCT)
Prior art keywords
diisocyanate
polyol
isocyanato
methyl
group
Prior art date
Application number
PCT/US2019/023314
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English (en)
Inventor
Alan Ekin
David P. Zielinski
Rick L. Adkins
Nigel Barksby
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 EP18163625.9A external-priority patent/EP3543271A1/fr
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 US15/933,507 external-priority patent/US20190292294A1/en
Priority claimed from EP18163620.0A external-priority patent/EP3543269A1/fr
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 US15/933,470 external-priority patent/US11292864B2/en
Priority claimed from US15/933,527 external-priority patent/US20190292296A1/en
Priority claimed from US15/933,495 external-priority patent/US11312881B2/en
Priority claimed from US15/933,511 external-priority patent/US11440988B2/en
Priority claimed from EP18181877.4A external-priority patent/EP3590988A1/fr
Priority claimed from EP18181876.6A external-priority patent/EP3590987A1/fr
Priority to CN201980034350.0A priority Critical patent/CN112105666B/zh
Priority to EP19713668.2A priority patent/EP3768756A1/fr
Application filed by Covestro Llc, Covestro Deutschland Ag filed Critical Covestro Llc
Publication of WO2019183315A1 publication Critical patent/WO2019183315A1/fr

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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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    • C08G18/08—Processes
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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
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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
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    • C08G18/2805—Compounds having only one group containing active hydrogen
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    • 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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    • 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
    • C08G18/3246—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
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    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
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    • C08G18/3225—Polyamines
    • C08G18/3253—Polyamines being in latent form
    • C—CHEMISTRY; METALLURGY
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    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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    • C08G18/3225—Polyamines
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    • C08G18/3256—Reaction products of polyamines with aldehydes or ketones
    • C—CHEMISTRY; METALLURGY
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    • 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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    • C—CHEMISTRY; METALLURGY
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    • 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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    • 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
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    • 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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    • 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
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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.
  • 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
  • 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”, ⁇ ,3-diazatidin-2,4-diones”, “2,4-dioxo-1 ,3-diazetidines”,“urethdiones” or“uretidiones”.
  • the polymer has few, if any, free isocyanate groups, which is achieved by controlling the stoichiometry of the polyisocyanate, polyol and by the use of a blocking agent.
  • the present invention 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.
  • the polyol may be neutralized by reaction with an acid scavenger at a temperature ranging from room temperature (21 ⁇ -24 ⁇ ) to 120 ⁇ .
  • the resulting allophanate polymer may be used to make coatings, adhesives, castings, composites, and sealants.
  • 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.
  • compositions and methods are described in terms of “comprising” various components or steps, the compositions and methods can also“consist essentially of” or“consist of” the various components or steps.
  • the present invention provides a reaction mixture comprising a polyuretdione resin; a neutralized polyol and a tertiary amine catalyst; and optionally, an additive package (e.g. flow control, wetting agent) and solvent.
  • the present invention further provides a method of making an allophanate polymer comprising reacting a polyuretdione resin with a neutralized polyol in the presence of a tertiary amine catalyst, wherein the reaction mixture optionally includes an additive package (e.g., flow control, wetting agent) and solvent.
  • the polyol may be neutralized by reaction with an acid scavenger at a temperature ranging from room temperature (21 ⁇ -24 ⁇ ) to 120 ⁇ .
  • an acid scavenger at a temperature ranging from room temperature (21 ⁇ -24 ⁇ ) to 120 ⁇ .
  • the present invention provides a m ethod for producing an allophanate polymer by the following route: Tertiary Amine
  • the inventive allophanate polymer system is particularly applicable in the production of 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.
  • adhesive or “adhesive compound” refer to any substance that can adhere or bond two items together. Implicit in the definition of an "adhesive composition” or “adhesive formulation” is the concept that the composition or formulation is a combination or mixture of more than one species, component or compound, which can include adhesive monomers, oligomers, and polymers along with other materials.
  • A“sealant composition” refers to a composition which may be applied to one or more surfaces to form a protective barrier, for example, to prevent ingress or egress of solid, liquid or gaseous material or alternatively to allow selective permeability through the barrier to gas and liquid. In particular, it may provide a seal between surfaces.
  • A“casting composition” refers to a mixture of liquid chemical components which is usually poured into a mold containing a hollow cavity of the desired shape, and then allowed to solidify.
  • A“composite” refers to a material made from two or more polymers, optionally containing other kinds of materials. A composite has different properties from those of the individual polymers/materials which make it up.
  • Cured refers to components and mixtures obtained from reactive curable original compound(s) or mixture(s) thereof which have undergone a chemical and/or physical changes such that the original compound(s) or mixture(s) is(are) transformed into a solid, substantially non-flowing material.
  • a typical curing process may involve crosslinking.
  • curable means that an original compound(s) or composition material(s) can be transformed into a solid, substantially non flowing material by means of chemical reaction, crosslinking, radiation crosslinking, or the like.
  • compositions of the invention are curable, but unless otherwise specified, the original compound(s) or composition material(s) is(are) not cured.
  • the components useful in the present invention comprise a polyisocyanate.
  • polyisocyanate refers to compounds comprising at least two unreacted isocyanate groups, such as three or more unreacted isocyanate groups.
  • the polyisocyanate may comprise diisocyanates such as linear aliphatic polyisocyanates, aromatic polyisocyanates, cycloaliphatic polyisocyanates and aralkyl
  • uretdiones particularly preferred are those blocked isocyanates known as uretdiones.
  • the uretdiones useful in the invention may be obtained by catalytic dimerization of polyisocyanates by methods which are known to those skilled in the art.
  • dimerization catalysts include, but are not limited to, trialkylphosphines,
  • aminophosphines and aminopyradines such as dimethylaminopyridines, and tris(dimethylamino)phosphine, as well as any other dimerization catalyst.
  • the result of the dimerization reaction depends, in a manner known to the skilled person, on the catalyst used, on the process conditions and on the polyisocyanates employed.
  • products it is possible for products to be formed which contain on average more than one uretdione group per molecule, the number of uretdione groups being subject to a distribution.
  • the (poly)uretdiones may optionally contain isocyanurate, biuret, allophanate, and iminooxadiazine dione groups in addition to the uretdione groups.
  • the uretdiones are NCO-functional compounds and may be subjected to a further reaction, for example, blocking of the free NCO groups or further reaction of NCO groups with NCO-reactive compounds having a functionality of two or more to extend the uretdiones to form polyuretdione prepolymers.
  • Suitable blocking agents include, but are not limited to, alcohols, lactams, oximes, malonates, alkyl acetoacetates, triazoles, phenols, imidazoles, pyrazoles and amines, such as butanone oxime,
  • diisopropylamine 1 ,2,4-triazole, dimethyl-1 ,2,4-triazole, imidazole, diethyl malonate, ethyl acetoacetate, acetone oxime, 3,5-dimethylpyrazole, caprolactam, N-tert-butylbenzylamine and cyclopentanone including mixtures of these blocking agents.
  • NCO-reactive compounds with a functionality of two or more include polyols.
  • the NCO-reactive compounds are used in amounts sufficient to react with all free NCO groups in the uretdione.
  • free NCO groups it is meant all NCO groups not present as part of the uretdione, isocyanurate, biuret, allophanate and iminooxadiazine dione groups.
  • the resulting polyuretdione contains at least 2, such as from 2 to 10 uretdione groups. More preferably, the polyuretdione contains from 5% to 45% uretdione, 10% to 55% urethane, and less than 2% isocyanate groups. The percentages are by weight based on total weight of resin containing uretdione, urethane, and isocyanate.
  • Suitable polyisocyanates for producing the uretdiones useful in embodiments of the invention include, organic diisocyanates represented by the formula
  • R represents an organic group obtained by removing the isocyanate groups from an organic diisocyanate having (cyclo)aliphatically bound isocyanate groups and a molecular weight of 1 12 to 1000, preferably 140 to 400.
  • Preferred diisocyanates for the invention are those represented by the formula wherein 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.
  • Examples of the organic diisocyanates which are particularly suitable for the present invention include 1 ,4-tetramethylene diisocyanate, 1 ,6-hexamethylene diisocyanate (HDI), 2,2,4-trimethyl-1 ,6-hexamethylene diisocyanate, 1 ,12-dodecamethylene diisocyanate, cyclohexane-1 ,3- and 1 ,4-diisocyanate, 1 -isocyanato-2-isocyanato-methyl cyclopentane, 1 - isocyanato-3-isocyanatomethyl-3, 5, 5-trimethyl cyclohexane (isophorone diisocyanate or IPDI), bis-(4-isocyanatocyclohexyl)methane, 1 ,3- and 1 ,4- bis(isocyanatomethyl)-cyclohexane, bis-(4-isocyanato-3-methyl- cyclohexy
  • diisocyanate 1 -isocyanato-1 -methyl-4(3)-isocyanato-methyl cyclohexane, and 2,4- and 2,6-hexahydrotoluene diisocyanate, toluene diisocyanate (TDI), diphenylmethane diisocyanate (MDI), pentane diisocyanate (PDI) - bio-based, and, isomers of any of these; or combinations of any of these. Mixtures of diisocyanates may also be used.
  • Preferred diisocyanates include 1 ,6-hexamethylene diisocyanate, isophorone diisocyanate, and bis(4-isocyanatocyclohexyl)-methane because they are readily available and yield relatively low viscosity polyuretdione polyurethane oligomers.
  • the uretdiones may comprise from 35% to 85% resin solids in the composition of present invention, excluding solvents, additives or pigments. In other embodiments, from 50% to 85% and in still other embodiments, 60% to 85%.
  • the uretdiones may comprise any resin solids amount ranging between any combinations of these values, inclusive of the recited values.
  • the 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 examples 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 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. Among the acids which are useful are phthalic acid, isophthalic acid, terephthalic acid, tetrahydrophthalic acid,
  • polycarboxyl ic acids such as trimellitic acid and tricarballylic acid (where acids are referred to above, it is understood that the anhydrides of those acids which form anhydrides can be used in place of the acid).
  • lower alkyl esters of acids such as dimethyl glutamate can be used.
  • polyester polyols formed from polybasic acids and polyols polycaprolactone-type polyesters can also be employed. These products are formed from the reaction of a cyclic lactone such as e-caprolactone with a polyol with primary hydroxyls such as those mentioned above. Such products are described in U.S. Pat. No.
  • 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-ethyl hexyl methacrylate and n-butyl acrylate.
  • copolymerizable monomers which can be copolymerized with the hydroxyalkyl (meth)acrylates include ethylenically unsaturated materials such as monoolefinic and diolefinic hydrocarbons, halogenated
  • monoolefinic and diolefinic hydrocarbons unsaturated esters of organic and inorganic acids, amides and esters of unsaturated acids, nitriles and unsaturated acids and the like.
  • monomers include styrene, 1 ,3-butadiene, acrylamide, acrylonitrile, a-methyl styrene, a-methyl chlorostyrene, vinyl butyrate, vinyl acetate, alkyl chloride, divinyl benzene, diallyl itaconate, triallyl cyanurate and mixtures thereof.
  • these other ethylenically unsaturated materials are used in admixture with the above-mentioned acrylates and methacrylates.
  • the polyol may be a polyurethane polyol.
  • These polyols can be prepared by reacting any of the above-mentioned polyols with a minor amount of polyisocyanate (OH/NCO equivalent ratio greater than 1 :1 ) so that free primary hydroxyl groups are present in the product.
  • polyisocyanate OH/NCO equivalent ratio greater than 1 :1
  • mixtures of both high molecular weight and low molecular weight polyols such as those mentioned above may be used.
  • Suitable hydroxy-functional polycarbonate polyols may be those prepared by reacting monomeric diols (such as 1 ,4-butanediol, 1 ,6- hexanediol, di-, tri- or tetraethylene glycol, di-, tri- or tetrapropylene glycol, 3-methyl-1 ,5-pentanediol, 4,4'-dimethylolcyclohexane and mixtures thereof) with diaryl carbonates (such as diphenyl carbonate, dialkyl carbonates (such as dimethyl carbonate and diethyl carbonate), alkylene carbonates (such as ethylene carbonate or propylene carbonate), or phosgene.
  • monomeric diols such as 1 ,4-butanediol, 1 ,6- hexanediol, di-, tri- or tetraethylene glycol, di-, tri- or tetrapropylene glycol, 3-methyl
  • the polyol is N-(2-aminoethyl)-2-aminoethyl
  • Acid scavengers should be covalently bonded to the acidic groups within the polyol.
  • the acid scavengers may be selected from carbodiimides, anhydrides, epoxies, trialkylorthoformates, amine compounds, and oxazolines.
  • the present inventors believe, without wishing to be bound to any specific theory, that these acid scavengers covalently bind to carboxylic and acrylic acid groups within the polyols.
  • Such compounds are commercially available from a variety of suppliers such as for example, the monomeric carbodiimides sold under the
  • the neutralization is conducted at any temperature ranging from room temperature (21 ⁇ - 24 ⁇ ) to 120 ⁇ , in other embodiments from room temp erature (21 ⁇ - 24 ⁇ ) to 800 and in certain embodiments at room te mperature (210 - 240).
  • suitable solvents include, but are not limited to aliphatic and aromatic hydrocarbons such as toluene, xylene, isooctane, acetone, butanone, methyl ethyl ketone, methyl amyl ketone, methyl isobutyl ketone, ethyl acetate, butyl acetate, pentyl acetate,
  • aliphatic and aromatic hydrocarbons such as toluene, xylene, isooctane, acetone, butanone, methyl ethyl ketone, methyl amyl ketone, methyl isobutyl ketone, ethyl acetate, butyl acetate, pentyl acetate,
  • compositions of the present invention may further include any of a variety of additives such as defoamers, devolatilizers, surfactants, thickeners, flow control additives, colorants (including pigments and dyes) or surface additives.
  • additives such as defoamers, devolatilizers, surfactants, thickeners, flow control additives, colorants (including pigments and dyes) or surface additives.
  • the 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.
  • the 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.
  • the composition of the present invention may be applied as multiple layers as needed.
  • POLYOL A an aromatic free, branched hydroxyl-bearing
  • polyester polyol commercially available from Covestro as DESMOPHEN 775 XP;
  • POLYOL C hydroxyl-functional acrylic polyol commercially available from Nuplex as Setalux D A 870 BA.
  • ADDITIVE A an active anti-hydrolysis agent for polyester polyurethanes, being used here as an acid scavenger for acidic groups within the polyols, commercially available from Rhein Chemie as STABAXOL I;
  • ADDITIVE B a surface additive on polyacrylate-basis for
  • ADDITIVE C epoxy reactive diluent being used here as an acid scavenger for acidic groups within the polyols, commercially available from Air Products as Epodil 757.
  • 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.
  • Acid numbers were determined using a METTLER TOLEDO EASY PLUS titrator according to ASTM D7253-16 with 0.025 N KOH as the titrant.
  • test samples were prepared by applying 4 mils (100 pm) wet film (2 mils (50 pm) dry) thickness of the formulation onto iron phosphate pre-treated 4”x12” (10.2 cm x 30.5 cm) steel test panels (ACT B1000).
  • MEK double rubs were measured according to ASTM D4752- 10(2015). Results reported are an average of three readings for each formulation.
  • the coating formulation in Table I was prepared as follows: in a 100 ml_ plastic container 2.92 parts of POLYOL A, 0.12 parts ADDITIVE B, 1 .10 parts n-butyl acetate, 0.61 parts CATALYST A (in 10% n-butyl acetate) were added. The resulting mixture was mixed using a
  • the first process involves neutralization of POLYOL A by ADDITIVE A at 120 ⁇ for 2 hours followed by cooling down to room temperature. This process simulates neutralization in a polyester polyol reactor.
  • Table IV summarizes the acid number readings of the POLYOL A and ADDITIVE A mixture after being mixed/reacted for one and seven days. After the acid numbers were determined, coating formulations were prepared followed by application onto substrates. MEK double rubs and microhardness readings were determined one day after application. Table IV
  • the second process involved neutralization of POLYOL A by ADDITIVE A at 800 for several days followed by coo ling down to room temperature. This process simulates neutralization in a hot storage area for viscous materials.
  • Table V summarizes the acid number readings of the POLYOL A and ADDITIVE A mixture after being mixed/reacted for one, two, three, seven, eight, and thirteen days. After the acid numbers were determined, coating formulations were prepared followed by application onto substrates. MEK double rubs and microhardness readings were determined one day after application.
  • the third process involved neutralization of POLYOL A by ADDITIVE A at room temperature for several days. This process simulates neutralization in a warehouse that was kept at room
  • Table VI summarizes the acid number readings of the POLYOL A and ADDITIVE A mixture after being mixed/reacted for one, seven, thirteen, twenty one, twenty eight, and fifty six days. After the acid numbers were determined, coating formulations were prepared followed by application onto substrates. MEK double rubs and microhardness readings were determined one day after application. Table V
  • Table VII summarizes two coating formulations for
  • Example A was based on POLYOL B without any acid scavenger (ADDITIVE C), whereas Example B was based on POLYOL B with acid scavenger (ADDITIVE C) that was neutralized using the second process for seven days. Coating formulations were prepared followed by application onto substrates. MEK double rubs and
  • microhardness readings were determined one, four, seven, and fourteen days after application.
  • MEK double rubs and microhardness readings were determined after curing in an electric oven for thirty minutes at 600, 800, 1000, 1200, and 1400.
  • Table VIII summarizes MEK double rubs and microhardness results of the formulation from Table VII over time.
  • Table IX summarizes MEK double rubs and microhardness results of the formulation from Table VII cured at different temperatures.
  • Example C was based on POLYOL C without any acid scavenger (ADDITIVE A), while Example D was based on POLYOL C with acid scavenger (ADDITIVE A) that was neutralized using the second process for seven days.
  • Coating formulations were prepared, followed by application onto substrates. MEK double rubs and Microhardness readings were determined one, four, seven, and fourteen days after application.
  • Table XI summarizes MEK double rubs and microhardness results of the formulation from Table X over time.
  • Tables X, and XI summarize coating formulations and performances where Example C contained an acrylic polyol without an acid scavenger. Furthermore, Example D contained an acrylic polyol with an acid scavenger, ADDITIVE A. As can be appreciated by reference to Tables X, and XI, it will be apparent to those skilled in the art that neutralization of polyol has a positive impact on coating performance over time.
  • the allophanates produced by the present invention are particularly applicable in or as coatings, adhesives, castings, composites, and sealants with good performance.
  • a reaction mixture comprising: a polyuretdione resin; a neutralized polyol; and a tertiary amine catalyst; and optionally, an additive package selected from the group consisting of flow control additives, wetting agents, and solvents.
  • a method of making an allophanate polymer comprising: reacting a polyuretdione resin and a neutralized polyol in the presence of a tertiary amine catalyst. [0087] 13. The method according to clause 12, wherein the
  • composition further includes an additive package selected from the group consisting of flow control additives, and wetting agents, and solvents.
  • polyuretdione resin comprises the reaction product of catalytic dimerization of an isocyanate.
  • HDI 1,6-hexamethylene diisocyanate
  • 2,2,4-trimethyl-1 ,6-hexamethylene diisocyanate 1,12-dodecamethylene diisocyanate
  • TDI toluene diisocyanate
  • MDI diphenylmethane diisocyanate
  • PDI pentane diisocyanate
  • the tertiary amine catalyst comprises 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,
  • polyol is selected from the group consisting of polyalkylene ether polyol, polyester polyols hydroxyl containing polycaprolactones, hydroxyl-containing (meth)acrylic polymers, polycarbonate polyols, polyurethane polyols and combinations thereof.
  • An allophanate polymer made by a method comprising: reacting a polyuretdione resin and a neutralized polyol in the presence of a tertiary amine catalyst.
  • the tertiary amine catalyst comprises 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,
  • the solvent is selected from the group consisting of toluene, xylene, isooctane, acetone, butanone, methyl ethyl ketone, methyl amyl ketone, methyl isobutyl ketone, ethyl acetate, butyl acetate, pentyl acetate, tetrahydrofuran, ethyl ethoxypropionate, N-methyl-pyrrolidone,
  • the neutralized polyol comprises the reaction product of a polyol and an acid scavenger.

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  • Wood Science & Technology (AREA)
  • Life Sciences & Earth Sciences (AREA)
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Abstract

La présente invention concerne un mélange réactionnel comprenant une résine de polyurétdione, un polyol neutralisé, un catalyseur amine tertiaire, et facultativement, un ensemble d'additifs choisi dans le groupe constitué par des additifs de régulation d'écoulement, des agents mouillants et des solvants. La présente invention concerne également des procédés de fabrication d'allophanates qui sont particulièrement applicables dans ou sous la forme de revêtements, d'adhésifs, de moulages, de composites et de produits d'étanchéité ayant de bonnes performances.
PCT/US2019/023314 2018-03-23 2019-03-21 Neutralisation d'acide polyol pour durcissement d'urétdione à basse température WO2019183315A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
CN201980034350.0A CN112105666B (zh) 2018-03-23 2019-03-21 用于低温脲二酮固化的多元醇酸中和
EP19713668.2A EP3768756A1 (fr) 2018-03-23 2019-03-21 Neutralisation d'acide polyol pour durcissement d'urétdione à basse température

Applications Claiming Priority (30)

Application Number Priority Date Filing Date Title
US15/933,475 US11008416B2 (en) 2018-03-23 2018-03-23 Aqueous, curable composition, comprising dispersed uretdione prepolymer, reactant and azolate
US15/933,527 2018-03-23
EP18163625.9 2018-03-23
US15/933,507 US20190292294A1 (en) 2018-03-23 2018-03-23 One component allophanate formulations through basecoat catalyst migration
US15/933,470 2018-03-23
EP18163620.0A EP3543269A1 (fr) 2018-03-23 2018-03-23 Dispersions de polyuréthane contenant de l'uretdione comprenant des groupes hydrophiles
US15/933,500 2018-03-23
US15/933,570 US10731051B2 (en) 2018-03-23 2018-03-23 Basecoat acid neutralization through inorganic salts
US15/933,475 2018-03-23
US15/933,487 2018-03-23
EP18163625.9A EP3543271A1 (fr) 2018-03-23 2018-03-23 Compositions aqueuses contenant des groupes urétdione et son procede de fabrication
EP18163621.8 2018-03-23
EP18163621.8A EP3543270A1 (fr) 2018-03-23 2018-03-23 Système catalyseur pour dispersions d'uretdions
EP18163620.0 2018-03-23
US15/933,495 US11312881B2 (en) 2018-03-23 2018-03-23 One component polyurethane/allophanate formulations with reactive reducer
US15/933,570 2018-03-23
US15/933,511 2018-03-23
US15/933,527 US20190292296A1 (en) 2018-03-23 2018-03-23 Polyol acid neutralization for low temperature uretdione curing
US15/933,511 US11440988B2 (en) 2018-03-23 2018-03-23 Polyuretdione-containing resin blend compositions
US15/933,495 2018-03-23
US15/933,553 2018-03-23
US15/933,507 2018-03-23
US15/933,500 US10696775B2 (en) 2018-03-23 2018-03-23 Curing for polyallophanate compositions through undercoat acid neutralization
US15/933,470 US11292864B2 (en) 2018-03-23 2018-03-23 Compositions using polyuretdione resins
US15/933,487 US20190292305A1 (en) 2018-03-23 2018-03-23 Uretdione based polyurethane compositions
US15/933,553 US10633477B2 (en) 2018-03-23 2018-03-23 Extended pot-life for low temperature curing polyuretdione resins
EP18181876.6 2018-07-05
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EP18181876.6A EP3590987A1 (fr) 2018-07-05 2018-07-05 Compositions aqueuses contenant des groupes urétdione et leur procédé de production
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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/EP2019/057065 WO2019180128A1 (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/US2019/023299 WO2019183308A1 (fr) 2018-03-23 2019-03-21 Compositions utilisant des résines polyurétdione
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/US2019/023286 WO2019183300A1 (fr) 2018-03-23 2019-03-21 Composition aqueuse durcissable comprenant un prépolymère d'urétdione dispersé, un réactif et un azolate
PCT/US2019/023290 WO2019183304A1 (fr) 2018-03-23 2019-03-21 Compositions de polyuréthane à base d'uretdione
PCT/US2019/023297 WO2019183307A1 (fr) 2018-03-23 2019-03-21 Compositions de mélange de résines contenant des polyuretdione
PCT/US2019/023314 WO2019183315A1 (fr) 2018-03-23 2019-03-21 Neutralisation d'acide polyol pour durcissement d'urétdione à basse température
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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PCT/EP2019/057065 WO2019180128A1 (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
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/US2019/023312 WO2019183313A1 (fr) 2018-03-23 2019-03-21 Durée de vie en pot prolongée pour des résines polyurétdione à durcissement à basse température
PCT/US2019/023286 WO2019183300A1 (fr) 2018-03-23 2019-03-21 Composition aqueuse durcissable comprenant un prépolymère d'urétdione dispersé, un réactif et un azolate
PCT/US2019/023290 WO2019183304A1 (fr) 2018-03-23 2019-03-21 Compositions de polyuréthane à base d'uretdione
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CN111886272B (zh) 2022-11-15
EP3768750A1 (fr) 2021-01-27
CN111886273A (zh) 2020-11-03
CN112105666A (zh) 2020-12-18
WO2019183300A1 (fr) 2019-09-26
CN111868133A (zh) 2020-10-30
EP3768749A1 (fr) 2021-01-27
CN111886271A (zh) 2020-11-03
EP3768754A1 (fr) 2021-01-27
CN112041367A (zh) 2020-12-04
EP3768757A1 (fr) 2021-01-27
WO2019183307A1 (fr) 2019-09-26
CN112105666B (zh) 2023-05-23
EP3768751A1 (fr) 2021-01-27
WO2019180128A1 (fr) 2019-09-26
WO2019180131A1 (fr) 2019-09-26
EP3768759A1 (fr) 2021-01-27
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WO2019183323A1 (fr) 2019-09-26
CN112004853B (zh) 2023-07-28
EP3768747A1 (fr) 2021-01-27
CN112105665A (zh) 2020-12-18
EP3768755A1 (fr) 2021-01-27
EP3768748A1 (fr) 2021-01-27
WO2019183313A1 (fr) 2019-09-26
EP3768758A1 (fr) 2021-01-27
EP3768753A1 (fr) 2021-01-27
WO2019183308A1 (fr) 2019-09-26
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WO2019183330A1 (fr) 2019-09-26

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