EP3768757A1 - One component allophanate formulations through basecoat catalyst migration - Google Patents
One component allophanate formulations through basecoat catalyst migrationInfo
- Publication number
- EP3768757A1 EP3768757A1 EP19713669.0A EP19713669A EP3768757A1 EP 3768757 A1 EP3768757 A1 EP 3768757A1 EP 19713669 A EP19713669 A EP 19713669A EP 3768757 A1 EP3768757 A1 EP 3768757A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- diisocyanate
- methyl
- allophanate
- acetate
- isocyanato
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
- C08G18/798—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing urethdione groups
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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
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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
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- C08G18/20—Heterocyclic amines; Salts thereof
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- C08G18/2063—Heterocyclic amines; Salts thereof containing condensed heterocyclic rings having two nitrogen atoms in the condensed ring system
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- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
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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
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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
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/3246—Polyamines heterocyclic, the heteroatom being oxygen or nitrogen in the form of an amino group
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- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3225—Polyamines
- C08G18/325—Polyamines containing secondary or tertiary amino groups
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- C—CHEMISTRY; METALLURGY
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- 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
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- C—CHEMISTRY; METALLURGY
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/3225—Polyamines
- C08G18/3253—Polyamines being in latent form
- C08G18/3256—Reaction products of polyamines with aldehydes or ketones
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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
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4862—Polyethers containing at least a part of the ether groups in a side chain
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- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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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
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08G18/751—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
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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
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- C08G18/7818—Nitrogen containing -N-C=0 groups containing ureum or ureum derivative groups
- C08G18/7831—Nitrogen containing -N-C=0 groups containing ureum or ureum derivative groups containing biuret groups
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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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- C08G18/797—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
- C09D175/04—Polyurethanes
- C09D175/06—Polyurethanes from polyesters
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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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- 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 a one component allophanate composition used in
- the catalyst migrates to the one component allophanate composition and catalyzes the system.
- Polyurethane-forming compositions are widely used in a variety of commercial, industrial and household applications, such as in automotive clear-coat and seat cushion applications.
- Polyurethane systems that employ isocyanates which are pre-reacted with monofunctional reagents to form relatively thermally labile compounds are called blocked isocyanates.
- Uretdiones are a type of blocked isocyanate.
- Uretdiones are typically prepared by dimerizing isocyanate to form uretdione(s) with unreacted isocyanate end-groups which can then be extended with a polyol to form a polymeric material containing two or more uretdione groups in the polymer chain.
- uretdiones are referred to as“1 ,3-diaza-2,4- cyclobutanones”,“1 ,3-diazatidin-2,4-diones”,“2,4-dioxo-1 ,3-diazetidines”, “urethdiones” or“uretidiones”.
- the polymer has few, if any, free isocyanate groups, which is achieved by controlling the stoichiometry of the polyisocyanate, polyol and by the use of a blocking agent.
- Polyuretdiones may react with polyols in the presence of tertiary amine catalysts and thus do not form stable systems in terms of shelf-life. Therefore, polyuretdiones and polyols cannot form one component systems in the presence of suitable tertiary amine catalysts.
- tertiary amine catalysts To the best of the present inventors’ knowledge, no one has developed a cross-linking approach using a one component allophanate composition in conjunction with a basecoat containing a catalyst in which the one component allophanate composition is applied to the basecoat, the catalyst migrates to the one component allophanate composition and catalyzes the system.
- 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.
- This cross-linking approach provides for the use of a one component allophanate composition in conjunction with a basecoat containing a tertiary amine catalyst in which the one component allophanate composition is applied to the basecoat, the catalyst migrates to the clear-coat and catalyzes the system.
- 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 one component allophanate composition comprising a neutralized polyol; a polyuretdione resin; and an optional reducer.
- the present invention provides a method of making a one component allophanate composition comprising combining a polyuretdione resin and a neutralized polyol in the presence of an optional reducer.
- the present invention provides a system comprising a one component allophanate composition and a catalyst containing a basecoat, wherein the one component allophanate composition comprises a neutralized polyol, a polyuretdione resin and an optional reducer, and wherein the catalyst comprises a tertiary amine.
- the present invention provides an allophanate system made by a method comprising combining a neutralized polyol with a polyuretdione resin in the presence of an optional reducer to produce a one component allophanate composition, and contacting the one component allophanate composition with a basecoat comprising a tertiary amine catalyst.
- the present invention provides a method for producing an allophanate polymer by the following route:
- inventive allophanate polymer system is particularly applicable in coatings, adhesives, castings, composites, and sealants.
- polymer encompasses prepolymers, oligomers and both homopolymers and copolymers; the prefix “poly” in this context referring to two or more.
- molecular weight when used in reference to a polymer, refers to the number average molecular weight, unless otherwise specified.
- polyol refers to compounds comprising at least two free hydroxy groups. Polyols include polymers comprising pendant and terminal hydroxy groups.
- coating composition refers to a mixture of chemical components that will cure and form a coating when applied to a substrate.
- 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
- the barrier may provide a seal between surfaces.
- A“casting composition” refers to a mixture of liquid chemical components which is usually poured into a mold containing a hollow cavity of the desired shape, and then allowed to solidify.
- A“composite” refers to a material made from two or more polymers, optionally containing other kinds of materials. A composite has different properties from those of the individual polymers/materials which make it up.
- Cured refers to components and mixtures obtained from reactive curable original compound(s) or mixture(s) thereof which have undergone a chemical and/or physical changes such that the original compound(s) or mixture(s) is(are) transformed into a solid, substantially non-flowing material.
- a typical curing process may involve crosslinking.
- curable means that an original compound(s) or composition material(s) can be transformed into a solid, substantially non flowing material by means of chemical reaction, crosslinking, radiation crosslinking, or the like.
- compositions of the invention are curable, but unless otherwise specified, the original compound(s) or composition material(s) is(are) not cured.
- basecoat means the first (undermost) layer applied to the surface of a substrate prior to application of a subsequent or finishing coat.
- the term encompasses basecoats, undercoats, and tiecoats.
- the components useful in the present invention comprise a polyisocyanate.
- polyisocyanate refers to compounds comprising at least two unreacted isocyanate groups, such as three or more unreacted isocyanate groups.
- the polyisocyanate may comprise diisocyanates such as linear aliphatic polyisocyanates, aromatic polyisocyanates, cycloaliphatic polyisocyanates and aralkyl
- uretdiones particularly preferred are those blocked isocyanates known as uretdiones.
- the uretdiones useful in the invention may be obtained by catalytic dimerization of polyisocyanates by methods which are known to those skilled in the art.
- dimerization catalysts include, but are not limited to, trialkylphosphines,
- aminophosphines and aminopyradines such as dimethylaminopyridines, and tris(dimethylamino)phosphine, as well as any other dimerization catalyst.
- the result of the dimerization reaction depends, in a manner known to the skilled person, on the catalyst used, on the process conditions and on the polyisocyanates employed.
- products it is possible for products to be formed which contain on average more than one uretdione group per molecule, the number of uretdione groups being subject to a distribution.
- the (poly)uretdiones may optionally contain isocyanurate, biuret, allophanate, and iminooxadiazine dione groups in addition to the uretdione groups.
- the uretdiones are NCO-functional compounds and may be subjected to a further reaction, for example, blocking of the free NCO groups or further reaction of NCO groups with NCO-reactive compounds having a functionality of two or more to extend the uretdiones to form polyuretdione prepolymers.
- Suitable blocking agents include, but are not limited to, alcohols, lactams, oximes, malonates, alkyl acetoacetates, triazoles, phenols, imidazoles, pyrazoles and amines, such as butanone oxime,
- diisopropylamine 1 ,2,4-triazole, dimethyl-1 ,2,4-triazole, imidazole, diethyl malonate, ethyl acetoacetate, acetone oxime, 3,5-dimethylpyrazole, caprolactam, N-tert-butylbenzylamine and cyclopentanone including mixtures of these blocking agents.
- NCO-reactive compounds with a functionality of two or more include polyols.
- the NCO-reactive compounds are used in amounts sufficient to react with all free NCO groups in the uretdione.
- free NCO groups it is meant all NCO groups not present as part of the uretdione, isocyanurate, biuret, allophanate and iminooxadiazine dione groups.
- the resulting polyuretdione contains at least 2, such as from 2 to 10 uretdione groups. More preferably, the polyuretdione contains from 5% to 45% uretdione, 10% to 55% urethane, and less than 2% isocyanate groups. The percentages are by weight based on total weight of resin containing uretdione, urethane, and isocyanate.
- Suitable polyisocyanates for producing the uretdiones useful in embodiments of the invention include, organic diisocyanates represented by the formula
- R represents an organic group obtained by removing the isocyanate groups from an organic diisocyanate having (cyclo)aliphatically bound isocyanate groups and a molecular weight of 1 12 to 1000, preferably 140 to 400.
- Preferred diisocyanates for the invention are those
- R represents a divalent aliphatic hydrocarbon group having from 4 to 18 carbon atoms, a divalent cycloaliphatic hydrocarbon group having from 5 to 15 carbon atoms, or a divalent araliphatic hydrocarbon group having from 7 to 15 carbon atoms.
- diisocyanate 1 -isocyanato-1 -methyl-4(3)-isocyanato-methyl cyclohexane, and 2,4- and 2,6-hexahydrotoluene diisocyanate, toluene diisocyanate (TDI), diphenylmethane diisocyanate (MDI), pentane diisocyanate (PDI) - bio-based, and, isomers of any of these; or combinations of any of these. Mixtures of diisocyanates may also be used.
- Preferred diisocyanates include 1 ,6-hexamethylene diisocyanate, isophorone diisocyanate, and bis(4-isocyanatocyclohexyl)-methane because they are readily available and yield relatively low viscosity polyuretdione polyurethane oligomers.
- the uretdiones may comprise from 35% to 85% resin solids in the composition of present invention, excluding solvents, additives or pigments. In other embodiments, from 50% to 85% and in still other embodiments 60% to 85%.
- the uretdiones may comprise any resin solids amount ranging between any combinations of these values, inclusive of the recited values.
- the polyols useful in the present invention may be either low molecular weight (65-399 Da, as determined by gel permeation
- the polyol of the present invention includes low molecular weight diols, triols and higher alcohols and polymeric polyols such as polyester polyols, polyether polyols, polycarbonate polyols, polyurethane polyols and hydroxy-containing (meth)acrylic polymers.
- the low molecular weight diols, triols and higher alcohols useful in the instant invention are known to those skilled in the art. In many embodiments, they are monomeric and have hydroxy values of 200 and above, usually within the range of 1500 to 200.
- Such materials include aliphatic polyols, particularly alkylene polyols containing from 2 to 18 carbon atoms. Examples include ethylene glycol, 1 ,4-butanediol, 1 ,6- hexanediol; cycloaliphatic polyols such as cyclohexane dimethanol.
- triols and higher alcohols 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.
- One commonly utilized oxyalkylation method is by reacting a polyol with an alkylene oxide, for example, ethylene oxide in the presence of an acidic or basic catalyst.
- Polyester polyols can also be used as a polymeric polyol component in the certain embodiments of the invention.
- the polyester polyols can be prepared by the polyesterification of organic 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.
- polyester polyols formed from polybasic acids and polyols can also be employed. These products are formed from the reaction of a cyclic lactone such as
- 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.
- 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.
- Examples of such 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.
- Suitable hydroxy-functional polycarbonate polyols may be those prepared by reacting monomeric diols (such as 1 ,4-butanediol, 1 ,6- hexanediol, di-, tri- or tetraethylene glycol, di-, tri- or tetrapropylene glycol, 3-methyl-1 ,5-pentanediol, 4,4'-dimethylolcyclohexane and mixtures thereof) with diaryl carbonates (such as diphenyl carbonate, dialkyl carbonates (such as dimethyl carbonate and diethyl carbonate), alkylene carbonates (such as ethylene carbonate or propylene carbonate), or phosgene.
- monomeric diols such as 1 ,4-butanediol, 1 ,6- hexanediol, di-, tri- or tetraethylene glycol, di-, tri- or tetrapropylene glycol, 3-methyl
- a minor amount of higher functional, monomeric polyols such as trimethylolpropane, glycerol or pentaerythritol, may be used.
- the polyol 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
- molecular weight polyols such as those mentioned above may be used.
- the polyol is N-(2-aminoethyl)-2-aminoethyl
- Acid scavengers should be covalently bonded to the acidic groups within the polyol.
- Acid scavengers can be selected from carbodiimides, anhydrides, epoxies, trialkylorthoformates, amine compounds, or oxazoline. 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
- Urethane reducers come 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,
- 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,
- 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.
- POLYOL A an aromatic free, branched hydroxyl-bearing
- polyester polyol commercially available from Covestro as DESMOPHEN 775 XP;
- polyurethanes being used as an acid scavenger for acidic groups within the polyols, commercially available from Rhein Chemie as STABAXOL I; ADDITIVE B a surface additive on polyacrylate-basis for solvent- borne coating systems and printing inks,
- URETDIONE A a 1 -isocyanato-3-isocyanatomethyl-3, 5, 5-trimethyl cyclohexane (isophorone diisocyanate or IPDI)- based uretdione prepolymer, proprietary product of Covestro LLC, having a uretdione equivalent weight of 1 ,276 and a viscosity of 817 cPs in 50% butyl acetate;
- REDUCER A a universal medium reducer, commercially
- RM UR 50 available from BASF as RM UR 50, recommended for use in temperatures between approximately 70°F - 85°F (21.1 *C - 29.40);
- BASECOAT A a black polyester refinish basecoat, commercially available from BASF as DIAMONT RM D403
- the basecoat Formulation B in Table 1 was prepared as follows. In a 200 ml_ plastic container 100 ml_ of BASECOAT A, 50 ml_ of
- REDUCER A 0.28 parts CATALYST A were added.
- the resulting mixture was mixed using a FLACKTEK speed mixer for one minute followed by application using a conventional FIVLP spray.
- the coating Formulation B in Table 1 was prepared as follows. POLYOL A had been reacted with ADDITIVE A prior to formulation. In a 500 mL plastic container 23.96 parts of the POLYOL A and ADDITIVE A reaction mixture, 0.94 parts ADDITIVE B, 8.51 parts n-butyl acetate, 161.85 parts URETDIONE A and 120 parts REDUCER A were added. The resulting mixture was mixed using a FLACKTEK speed mixer for one minute followed by application using a conventional HVLP spray.
- Iron phosphate treated ACT B1000 4”x12” (10.2 cm x 30.5 cm) test panels were sprayed with a polyurethane automotive primer before receiving basecoat followed by one component coating. Thickness of black polyester 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 microhardness and MEK double rubs.
- Films were cured at room temperature (21 ⁇ C - 241C) for four days and for five weeks before testing.
- Microhardness (Marten’s hardness) measurements were done using FISCFIERSCOPE FI100C instrument according to the method described in DIN EN ISO 14577. Microhardness readings were taken under a 20 mN test load run to a maximum of 5 pm indentation depths over a 20 second application time. Results reported are an average of three readings for each formulation.
- MEK double rubs were measured according to ASTM D4752- 10(2015). Results reported are an average of three readings for each formulation.
- Viscosities of the formulations in Table II were measured according to ASTM D7395-07(2012) using a BROOKFIELD RST
- Example A through E receive the same one component coating over basecoats that have different amounts of catalysts.
- the basecoat in Example A does not contain any catalyst;
- Examples B through E has incrementally increased amounts of catalyst added to the basecoat.
- one component coating curing is only triggered by the catalyst migrating from the basecoat.
- coating performance is improved significantly postulating that the one component coating curing is through migration of tertiary amine catalyst from the basecoat.
- Table II summarizes the viscosities of the one component coating used in examples A through E in Table I.
- the one component coating has all the components mixed except the catalyst.
- the inventive coating can be supplied as one component, it was placed in glass and tin containers and left at those temperatures for nine weeks. It will be apparent to those skilled in the art that none of the containers stored at any temperatures showed signs of viscosity increase thus showing that the inventive coating can be stored as one component.
- the one component allophanate polymers produced by the present invention are believed to be particularly applicable for coatings, adhesives, castings, composites, and sealants.
- a one component allophanate composition comprising a neutralized polyol a polyuretdione resin and optionally a reducer.
- composition further includes an additive package selected from the group consisting of flow control additives, wetting agents, and solvents.
- the method comprises at least one of spraying, dipping, flow coating, rolling, brushing, and pouring.
- 1 A method of making a one component allophanate composition comprising: combining a polyuretdione resin and a neutralized polyol in the presence of an optional reducer.
- polyuretdione resin comprises the reaction product of catalytic dimerization of an isocyanate.
- TDI toluene diisocyanate
- MDI diphenylmethane diisocyanate
- PDI pentane diisocyanate
- 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.
- a system comprising: a one component allophanate composition and a catalyst containing a basecoat, wherein the one component allophanate composition comprises a neutralized polyol, a polyuretdione resin and an optional reducer, and wherein the catalyst comprises a tertiary amine.
- 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.
- 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 method comprises at least one of spraying, dipping, flow coating, rolling, brushing, and pouring.
- the neutralized polyol comprises the reaction product of a polyol and an acid scavenger.
- polyuretdione resin comprises the reaction product of catalytic dimerization of an isocyanate.
- 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'- 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, iso
- the reducer 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 (trifl
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Abstract
Description
Claims
Applications Claiming Priority (16)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US15/933,527 US20190292296A1 (en) | 2018-03-23 | 2018-03-23 | Polyol acid neutralization for low temperature uretdione curing |
EP18163621.8A EP3543270A1 (en) | 2018-03-23 | 2018-03-23 | Catalyst system for uretdion dispersions |
US15/933,495 US11312881B2 (en) | 2018-03-23 | 2018-03-23 | One component polyurethane/allophanate formulations with reactive reducer |
EP18163620.0A EP3543269A1 (en) | 2018-03-23 | 2018-03-23 | Uretdione-containing polyurethane-dispersions comprising hydrophilic groups |
US15/933,507 US20190292294A1 (en) | 2018-03-23 | 2018-03-23 | One component allophanate formulations through basecoat catalyst migration |
EP18163625.9A EP3543271A1 (en) | 2018-03-23 | 2018-03-23 | Compositions containing uretdione groups and method for their preparation |
US15/933,500 US10696775B2 (en) | 2018-03-23 | 2018-03-23 | Curing for polyallophanate compositions through undercoat acid neutralization |
US15/933,475 US11008416B2 (en) | 2018-03-23 | 2018-03-23 | Aqueous, curable composition, comprising dispersed uretdione prepolymer, reactant and azolate |
US15/933,570 US10731051B2 (en) | 2018-03-23 | 2018-03-23 | Basecoat acid neutralization through inorganic salts |
US15/933,511 US11440988B2 (en) | 2018-03-23 | 2018-03-23 | Polyuretdione-containing resin blend compositions |
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 |
EP18181876.6A EP3590987A1 (en) | 2018-07-05 | 2018-07-05 | Aqueous compositions containing uretdione groups and method for their preparation |
EP18181877.4A EP3590988A1 (en) | 2018-07-05 | 2018-07-05 | Aqueous compositions containing uretdione groups and method for their preparation |
PCT/US2019/023319 WO2019183319A1 (en) | 2018-03-23 | 2019-03-21 | One component allophanate formulations through basecoat catalyst migration |
Publications (1)
Publication Number | Publication Date |
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EP3768757A1 true EP3768757A1 (en) | 2021-01-27 |
Family
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Family Applications (14)
Application Number | Title | Priority Date | Filing Date |
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EP19713668.2A Pending EP3768756A1 (en) | 2018-03-23 | 2019-03-21 | Polyol acid neutralization for low temperature uretdione curing |
EP19711129.7A Pending EP3768751A1 (en) | 2018-03-23 | 2019-03-21 | Aqueous uretdione group-containing compositions and method for producing same |
EP19713663.3A Withdrawn EP3768747A1 (en) | 2018-03-23 | 2019-03-21 | Aqueous, curable composition, comprising dispersed uretdione prepolymer, reactant and azolate |
EP19711125.5A Pending EP3768749A1 (en) | 2018-03-23 | 2019-03-21 | Aqueous uretdione group-containing compositions and method for producing same |
EP19713670.8A Withdrawn EP3768758A1 (en) | 2018-03-23 | 2019-03-21 | One component polyurethane/allophanate formulations with reactive reducer |
EP19713667.4A Withdrawn EP3768755A1 (en) | 2018-03-23 | 2019-03-21 | Compositions using polyuretdione resins |
EP19711128.9A Withdrawn EP3768745A1 (en) | 2018-03-23 | 2019-03-21 | Uretdione-containing polyurethane-dispersions comprising hydrophilic groups |
EP19713339.0A Pending EP3768752A1 (en) | 2018-03-23 | 2019-03-21 | Basecoat acid neutralization through inorganic salts |
EP19711127.1A Withdrawn EP3768748A1 (en) | 2018-03-23 | 2019-03-21 | Catalyst system for uretdione dispersions |
EP19713666.6A Withdrawn EP3768754A1 (en) | 2018-03-23 | 2019-03-21 | Polyuretdione-containing resin blend compositions |
EP19713665.8A Withdrawn EP3768753A1 (en) | 2018-03-23 | 2019-03-21 | Improved curing for polyallophanate compositions through undercoat acid neutralization |
EP19711126.3A Pending EP3768750A1 (en) | 2018-03-23 | 2019-03-21 | Aqueous uretdione group-containing compositions and method for producing same |
EP19713669.0A Withdrawn EP3768757A1 (en) | 2018-03-23 | 2019-03-21 | One component allophanate formulations through basecoat catalyst migration |
EP19714972.7A Withdrawn EP3768759A1 (en) | 2018-03-23 | 2019-03-21 | Extended pot-life for low temperature curing polyuretdione resins |
Family Applications Before (12)
Application Number | Title | Priority Date | Filing Date |
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EP19713668.2A Pending EP3768756A1 (en) | 2018-03-23 | 2019-03-21 | Polyol acid neutralization for low temperature uretdione curing |
EP19711129.7A Pending EP3768751A1 (en) | 2018-03-23 | 2019-03-21 | Aqueous uretdione group-containing compositions and method for producing same |
EP19713663.3A Withdrawn EP3768747A1 (en) | 2018-03-23 | 2019-03-21 | Aqueous, curable composition, comprising dispersed uretdione prepolymer, reactant and azolate |
EP19711125.5A Pending EP3768749A1 (en) | 2018-03-23 | 2019-03-21 | Aqueous uretdione group-containing compositions and method for producing same |
EP19713670.8A Withdrawn EP3768758A1 (en) | 2018-03-23 | 2019-03-21 | One component polyurethane/allophanate formulations with reactive reducer |
EP19713667.4A Withdrawn EP3768755A1 (en) | 2018-03-23 | 2019-03-21 | Compositions using polyuretdione resins |
EP19711128.9A Withdrawn EP3768745A1 (en) | 2018-03-23 | 2019-03-21 | Uretdione-containing polyurethane-dispersions comprising hydrophilic groups |
EP19713339.0A Pending EP3768752A1 (en) | 2018-03-23 | 2019-03-21 | Basecoat acid neutralization through inorganic salts |
EP19711127.1A Withdrawn EP3768748A1 (en) | 2018-03-23 | 2019-03-21 | Catalyst system for uretdione dispersions |
EP19713666.6A Withdrawn EP3768754A1 (en) | 2018-03-23 | 2019-03-21 | Polyuretdione-containing resin blend compositions |
EP19713665.8A Withdrawn EP3768753A1 (en) | 2018-03-23 | 2019-03-21 | Improved curing for polyallophanate compositions through undercoat acid neutralization |
EP19711126.3A Pending EP3768750A1 (en) | 2018-03-23 | 2019-03-21 | Aqueous uretdione group-containing compositions and method for producing same |
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CN110698622A (en) * | 2019-10-12 | 2020-01-17 | 北京长润化工有限公司 | Ketimine latent curing agent, reactive polyurethane hot melt adhesive with ketimine latent curing agent and application of reactive polyurethane hot melt adhesive |
CN113816812A (en) * | 2021-08-27 | 2021-12-21 | 湖北航天化学技术研究所 | Liquid urea speed reducer, preparation method and solid propellant |
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2019
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