WO2019183313A1 - Durée de vie en pot prolongée pour des résines polyurétdione à durcissement à basse température - Google Patents
Durée de vie en pot prolongée pour des résines polyurétdione à durcissement à basse température Download PDFInfo
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- WO2019183313A1 WO2019183313A1 PCT/US2019/023312 US2019023312W WO2019183313A1 WO 2019183313 A1 WO2019183313 A1 WO 2019183313A1 US 2019023312 W US2019023312 W US 2019023312W WO 2019183313 A1 WO2019183313 A1 WO 2019183313A1
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- Prior art keywords
- acid
- diisocyanate
- reaction mixture
- polyols
- isocyanato
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- 0 *N(C(N1*)=O)C1=O Chemical compound *N(C(N1*)=O)C1=O 0.000 description 1
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- 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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- C08G18/00—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
- C08G18/2009—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
- 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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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
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- C08G18/28—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
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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
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- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3203—Polyhydroxy compounds
- C08G18/3206—Polyhydroxy compounds aliphatic
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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
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- C08G18/3225—Polyamines
- C08G18/3234—Polyamines cycloaliphatic
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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
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- C08G18/3225—Polyamines
- C08G18/3246—Polyamines heterocyclic, the heteroatom being oxygen or nitrogen in the form of an amino group
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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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
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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
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3225—Polyamines
- C08G18/3253—Polyamines being in latent form
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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
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- C08G18/3253—Polyamines being in latent form
- C08G18/3256—Reaction products of polyamines with aldehydes or ketones
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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
- C08G18/40—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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- 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
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- C08G18/48—Polyethers
- C08G18/4862—Polyethers containing at least a part of the ether groups in a side chain
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- 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
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- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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- C08G18/721—Two or more polyisocyanates not provided for in one single group C08G18/73 - C08G18/80
- C08G18/725—Combination of polyisocyanates of C08G18/78 with other polyisocyanates
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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
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- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/73—Polyisocyanates or polyisothiocyanates acyclic
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
- C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
- C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
- C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
- C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
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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
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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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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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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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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
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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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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
- C09D175/06—Polyurethanes from polyesters
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives 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
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
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- C09J175/12—Polyurethanes from compounds containing nitrogen and active hydrogen, the nitrogen atom not being part of an isocyanate group
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2190/00—Compositions for sealing or packing joints
Definitions
- the present invention relates, in general to polymers, and more specifically, to compositions useful as coatings, adhesives, castings, composites, and sealants which are made with polyuretdiones and polyols in the presence of acid blocked tertiary amine catalysts to extend pot-life of the resultant coatings, adhesives, castings, composites, and sealants without diminishing performance.
- 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 a uretdione with unreacted isocyanate groups which can then be extended with a polyol to form a polymeric material containing two or more uretdione groups in the polymer chain.
- uretdiones are referred to as“1 ,3-diaza-2,4-cyclobutanones”,“1 ,3-diazatidin-2,4-diones”,“2,4-dioxo- 1 ,3-diazetidines”,“urethdiones” or“uretidiones”.
- the polymer has few, if any, free isocyanate groups, which is achieved by controlling the stoichiometry of the polyisocyanate, polyol and by the use of a blocking agent.
- the present invention 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 polyols in the presence of an acid-blocked tertiary amine catalyst in which the acid has a pKa of greater than 4.82.
- the tertiary amine catalyst may be activated at any temperature from room temperature (20-25'C) or ⁇ o130 ⁇ .
- the inventive compositions may extend the pot-life of resultant 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 polyol; and an acid- blocked tertiary amine catalyst; and optionally, an additive package (e.g. flow control, wetting agent) and solvent, wherein the acid has a pK a of greater than 4.82.
- the present invention further provides a method comprising, reacting a polyuretdione resin with a polyol in the presence of an acid-blocked tertiary amine catalyst, wherein the reaction mixture optionally includes an additive package (e.g., flow control, wetting agent) and solvent, and wherein the acid has a pK a of greater than 4.82.
- the acid-blocked tertiary amine catalyst may be activated at any temperature from room temperature (20 ⁇ ) to 130 ⁇ .
- inventive allophanate polymer 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.
- coating composition refers to a mixture of chemical components that will cure and form a coating when applied to a substrate.
- adheresive or “adhesive compound” refer to any substance that can adhere or bond two items together. Implicit in the definition of an "adhesive composition” or “adhesive formulation” is the concept that the composition or formulation is a combination or mixture of more than one species, component or compound, which can include adhesive monomers, oligomers, and polymers along with other materials.
- A“sealant composition” refers to a composition which may be applied to one or more surfaces to form a protective barrier, for example, to prevent ingress or egress of solid, liquid or gaseous material or 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.
- compositions 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
- polyisocyanates Particularly preferred in the present invention 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 2 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,
- NCO-reactive compounds with a functionality of two or more include polyols.
- the NCO-reactive compounds are used in amounts sufficient to react with all free NCO groups in the uretdione.
- free NCO groups it is meant all NCO groups not present as part of the uretdione, isocyanurate, biuret, allophanate and iminooxadiazine dione groups.
- the resulting polyuretdione contains at least 2, such as from 2 to 10 uretdione groups. More preferably, the polyuretdione contains from 5% to 45% uretdione, 10% to 55% urethane, and less than 2% isocyanate groups. The percentages are by weight based on total weight of resin containing uretdione, urethane, and isocyanate.
- Suitable polyisocyanates for producing the uretdiones useful in embodiments of the invention include, organic diisocyanates represented by the formula
- R represents an organic group obtained by removing the isocyanate groups from an organic diisocyanate having (cyclo)aliphatically bound isocyanate groups and a molecular weight of 112 to 1000, preferably 140 to 400.
- Preferred diisocyanates for the invention are those 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.
- 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), diphenyl methane diisocyanate (MDI), pentane diisocyanate (PDI)— bio-based, and, isomers of any of these; or combinations of any of these. Mixtures of diisocyanates may also be used.
- 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 tertiary amine in the tertiary amine catalyst includes, but is not limited to, triethylene diamine; substituted imidazoles such as 1-2 dimethylimidazole, 1 -methyl-2- hydroxyethylimidazole; N.N'dimethylpiperazine or substituted piperazines such as aminoethylpiperazine or bis(N-methyl piperazine)ethylurea or N.N'.N'trimethyl aminoethylpiperazine; N-methylpyrrolidines and substituted methyl pyrrolidines such as 2-aminoethyl-N,methylpyrrolidines or Bis(N- methylpyrrolidine)ethyl urea; or other tertiary aminoalkylureas or bis(tertiary amino alkyl) urea such as N,N-(3-dimethylaminopropyl)urea; 3- dimethylaminopropylamine; N l N
- the tertiary amine catalysts are acid blocked versions of 1 ,8-diazabicyclo[5.4.0]undec-7ene, 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.
- Suitable acids for blocking the tertiary amines in various embodiments of the invention include organic carboxylic acids including C1-C20 mono- or dicarboxylic acids, such as formic, acetic, propionic, butyric, caproic, carbolic, 2-ethyl-hexanoic, caprylic, cyanoacetic, pyruvic, benzoic, oxalic, malonic, succinic, phthalic, salicylic and maleic acids.
- organic carboxylic acids including C1-C20 mono- or dicarboxylic acids, such as formic, acetic, propionic, butyric, caproic, carbolic, 2-ethyl-hexanoic, caprylic, cyanoacetic, pyruvic, benzoic, oxalic, malonic, succinic, phthalic, salicylic and maleic acids.
- Examples of such acid-blocked tertiary amine catalysts useful in embodiments of the present invention include, but are not limited to, those available from Air Products under the POLYCAT, DABCO, LK and VERSALINK trade names, those available from Momentive Performance Materials under NIAX trade name; and the JEFFCAT catalysts from Huntsman.
- the acid-blocked tertiary amine catalysts may be heated to a temperature of 1000. In other embodiments, a broader temperature range of from room
- the present inventors have unexpectedly found that the pK a of the acid component of the acid-blocked tertiary amine catalyst has an effect on the pot-life and physical properties of the resultant materials.
- Those acids having a pKa of 4.82 and below appear to be less effective at prolonging pot-life and retaining physical properties.
- Those acids having a pKa of greater than 5.0 produce better results and those acids having a pKa of greater than 5.5 produce even better results.
- the present inventors believe that those acids having a pKa of from greater than 4.82 to 10 provide the best combination of pot-life and physical properties in the resultant coatings, adhesives, castings, composites, and sealants made from the compositions of the invention.
- the polyols useful in the present invention may be either low molecular weight (62-399 Da, as determined by gel permeation chromatography) or high molecular weight (400 to 10,000 Da, as determined by gel permeation chromatography) materials and in various embodiments will have average hydroxyl values as determined by ASTM E222-10, Method B, of between 1000 and 10, and preferably between 500 and 50.
- the polyols in the present invention include low molecular weight diols, triols and higher alcohols and polymeric polyols such as polyester polyols, polyether polyols, polyurethane polyols and hydroxy- containing (meth)acrylic polymers.
- the low molecular weight diols, triols and higher alcohols useful in the instant invention are known to those skilled in the art. In many embodiments, they are monomeric and have hydroxy values of 200 and above, usually within the range of 1500 to 200.
- Such materials include aliphatic polyols, particularly alkylene polyols containing from 2 to 18 carbon atoms. Examples include ethylene glycol, 1 ,4-butanediol, 1,6- hexanediol; cycloaliphatic polyols such as cyclohexane dimethanol.
- triols and higher alcohols examples include trimethylol propane and pentaerythritol. Also useful are polyols containing ether linkages such as diethylene glycol and triethylene glycol.
- the suitable polyols are polymeric polyols having hydroxyl values less than 200, such as 10 to 180.
- polymeric polyols include polyalkylene ether polyols, polyester polyols including hydroxyl-containing polycaprolactones, hydroxy-containing (meth)acrylic polymers, polycarbonate polyols and polyurethane polymers.
- polyether polyols examples include poly(oxytetramethylene) glycols, poly(oxyethylene) glycols, and the reaction product of ethylene glycol with a mixture of propylene oxide and ethylene oxide.
- polyether polyols formed from the oxyalkylation of various polyols, for example, glycols such as ethylene glycol, 1 ,4-butane glycol, 1 ,6-hexanediol, and the like, or higher polyols, such as trimethylol propane, pentaerythritol and the like.
- glycols such as ethylene glycol, 1 ,4-butane glycol, 1 ,6-hexanediol, and the like
- polyols such as trimethylol propane, pentaerythritol and the like.
- alkylene oxide for example, ethylene oxide in the presence of an acidic or basic catalyst.
- Polyester polyols can also be used as a polymeric polyol component in the certain embodiments of the invention.
- the polyester polyols can be prepared by the polyesterification of organic polycarboxyl ic acids or anhydrides thereof with organic polyols.
- the polycarboxyl ic acids and polyols are aliphatic or aromatic dibasic acids and diols.
- the diols which may be employed in making the polyester include alkylene glycols, such as ethylene glycol and butylene glycol, neopentyl glycol and other glycols such as cyclohexane dimethanol, caprolactone diol (for example, the reaction product of caprolactone and ethylene glycol), polyether glycols, for example, poly(oxytetramethylene) glycol and the like.
- alkylene glycols such as ethylene glycol and butylene glycol
- neopentyl glycol and other glycols such as cyclohexane dimethanol
- caprolactone diol for example, the reaction product of caprolactone and ethylene glycol
- polyether glycols for example, poly(oxytetramethylene) glycol and the like.
- other diols of various types and, as indicated, polyols of higher functionality may also be utilized in various embodiments of the invention.
- Such higher polyols can include, for example, trimethylol propane, trimethylol ethane, pentaerythritol, and the like, as well as higher molecular weight polyols such as those produced by oxyalkylating low molecular weight polyols.
- An example of such high molecular weight polyol is the reaction product of 20 moles of ethylene oxide per mole of trimethylol propane.
- the acid component of the polyester consists primarily of monomeric carboxylic acids or anhydrides having 2 to 18 carbon atoms per molecule.
- acids which are useful are phthalic acid, isophthalic acid, terephthalic acid, tetrahydrophthalic acid,
- 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-ethylhexyl methacrylate and n-butyl acrylate.
- copolymerizable monomers which can be copolymerized with the hydroxyalkyl (meth)acrylates include ethylenically unsaturated materials such as monoolefinic and diolefinic hydrocarbons, halogenated monoolefinic and diolefinic hydrocarbons, unsaturated esters of organic and inorganic acids, amides and esters of unsaturated acids, nitriles and unsaturated acids and the like.
- 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
- the polyol is neutralized, for example, by the addition of an acid scavenger.
- Acid scavengers should be covalently bonded to the acidic groups within the polyol.
- Acid scavengers may be from a family of reactants to carboxylic or acrylic acid groups such as 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.
- Such compounds are commercially available from a variety of suppliers, such as for example, the monomeric carbodiimides sold under the STABAXOL trade name from Rhein Chemie, and bis(2,6-diisopropylphenyl) carbodiimide sold as EUSTAB HS-700 by Eutec Chemical Co., Ltd.
- 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.
- 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.
- 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.
- 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 substrate by any methods known to those skilled in the art, including but not limited to, spraying, dipping, flow coating, rolling, brushing, pouring, and the like.
- inventive compositions may be applied in the form of paints or lacquers onto any compatible substrate, such as, for example, metals, plastics, ceramics, glass, and natural materials.
- the composition is applied as a single layer. In other embodiments, the inventive compositions 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
- CATALYST B a low emissive, acid-blocked (pK a s of 2.89 and
- CATALYST C an acid-blocked (pKa of 10.0), tertiary amine
- tertiary amine catalyst based on DBU, -40% DBU content commercially available from Air Products as POLYCAT SA-102;
- tertiary amine catalyst based on DBU -30% DBU content, commercially available from Momentive Performance Materials as NIAX A-575;
- CATALYST F an acid-blocked (pKas of 2.89 and 5.51), heat activated tertiary amine catalyst based on DBU, -30% DBU content, commercially available from Air Products as POLYCAT SA8;
- 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.
- Coating formulation 1 was prepared as follows: Prior to formulating 11.69 parts of POLYOL A and 0.12 parts of ADDITIVE A were mixed and stored at 80 ⁇ for one week. In a 200 mL plastic container 11.81 parts of the ADDITIVE A and POLYOL A mixture, 0.47 parts ADDITIVE B, 6.60 parts n-butyl acetate (BA), 0.25 parts CATALYST A were added. The resulting mixture was mixed using a FLACKTEK speed mixer for one minute. Then, 80.51 parts URETDIONE A solution (50% in n-butyl acetate) was added to the mixture. The resulting mixture was mixed for an additional minute followed by application using a drawdown bar onto test panels. The formulations of the other examples were made in a similar manner according to the amounts and ingredients listed in Table I.
- 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” x 12” (10.2 cm x 30.5 cm) steel test panels (ACT B1000).
- “Room temperature” films were cured at 20 ⁇ -25 ⁇ f or 24 hours before testing.
- The“100 ⁇ ” films were cured at 100 ⁇ for 30 minutes in an electric oven and left at room temperature for 24 hours before testing.
- Microhardness (“Marten’s hardness”) measurements were done using FISCHERSCOPE H100C 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.
- Table I includes data comparing the various forms of catalysts containing acid-blocked and unblocked DBU. Included are results of hardness testing, chemical resistance by way of MEK double rubs and pot- life by viscosity over time.
- Formulations of Examples 1 , 3, 5, 7, 9, and 1 1 are comparative in terms of DBU amounts (0.5% DBU loading (based on solids)) to the formulations of Examples 2, 4, 5, 6, 10, and 12 which utilize 1 % DBU catalyst (based on solids).
- the catalyst levels included in the Table I account for both DBU catalyst and acid blocking agent. Examples 3, 4, 5, and 6 show improvement in pot-life without sacrificing physical properties in comparison to unblocked catalysts of Examples 1 and 2.
- the pKa of the acid blocking agent has an effect on pot-life and physical properties.
- the pKa of acid blocking agent used in Examples 5 and 6 is 10 (Catalyst C), which shows improvement in pot-life without sacrificing physical properties.
- the pKa of acid blocking agent used in Examples 7 and 8 is 4.82 (Catalyst D), which shows improvement in pot-life; however, physical properties are lacking.
- the pKa of acid blocking agent used in Examples 9 and 10 is 2.97
- Catalyst E which again shows improvement in pot-life; however, physical properties are lacking.
- the acid blocking agent used in Examples 3, 4, 1 1 and 12 has two pKa values and is the same (Catalyst B and Catalyst F).
- Catalyst B and Catalyst F has the same acid blocking agent.
- Examples 3 and 4 (using Catalyst B) show improvement in pot-life without sacrificing physical properties.
- Examples 1 1 and 12 (using Catalyst F) show improvement in pot-life; however, physical properties are lacking. The reason for the difference is with the amount of DBU that is present in comparison to acidic groups.
- Catalyst B has -50% DBU in which both acid groups of pKa 2.89 and 5.51 are being used during blocking.
- Catalyst F has -30% DBU in which the majority of the DBU is being blocking with stronger acid of pKa 2.89 rather than pKa 5.51 .
- Comparison of performance of formulations using Catalyst B and F gives a great indication of the role of pKa of acid blocking agent where higher than pKa of 4.82 is needed in order to improve pot-life without sacrificing physical performance.
- compositions of the present invention are particularly applicable in or as coatings, adhesives, castings, composites, and sealants with good performance and extended pot-life.
- a reaction mixture comprising: a polyuretdione resin; a neutralized polyol; an acid-blocked tertiary amine catalyst; and optionally, an additive package selected from the group consisting of flow control additives, wetting agents, and solvents, wherein the acid has a pK a of greater than 4.82.
- 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 1,4- and 2,6-hexahydrotoluene diisocyanate
- toluene diisocyanate TDI
- diphenylmethane diisocyanate MDI
- pentane diisocyanate - bio-based, and, isomers of any of these.
- the acid-blocked tertiary amine catalyst comprises one selected from the group consisting of 1 ,8-diazabicyclo[5.4.0]undec-7ene, 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.
- a method of making a composition comprising: reacting a polyuretdione resin and a neutralized polyol in the presence of an acid- blocked tertiary amine catalyst, wherein the acid has a pK a of greater than 4.82.
- composition further includes an additive package selected from the group consisting of flow control additives, wetting agents, and solvents.
- polyuretdione resin comprises the reaction product of catalytic dimerization of an isocyanate.
- TDI toluene diisocyanate
- MDI diphenyl methane diisocyanate
- PDI pentane diisocyanate
- polyol is one or more selected from the group consisting of polyether polyols, polyester polyols, hydroxy-containing (meth)acrylic polymers and (meth)acrylic polyols, polyurethane polyol, polycaprolactone polyol, and combinations thereof.
- [0107] 35 A method of applying the reaction mixture made according to one of clauses 17 to 34, wherein the method comprises at least one of spraying, dipping, flow coating, rolling, brushing, and pouring.
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Abstract
La présente invention concerne un mélange de réaction comprenant une résine polyurétdione, un polyol neutralisé, un catalyseur d'amine tertiaire bloquée par un acide, et éventuellement, un lot d'additifs choisis dans le groupe constitué par les additifs de régulation de débit, les agents de mouillage, et les solvants, où l'acide a un pKa supérieur à 4,82. Les compositions préparées à partir du mélange de réaction selon la présente invention peuvent être catalysées à des températures allant de la température ambiante à 130 °C et se prêtent particulièrement bien dans les applications dans ou sous la forme de revêtements, adhésifs, moulages, composites et produits d'étanchéité ayant de bonnes performances et une durée de vie en pot prolongée.
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
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EP19714972.7A EP3768759A1 (fr) | 2018-03-23 | 2019-03-21 | Durée de vie en pot prolongée pour des résines polyurétdione à durcissement à basse température |
CN201980034098.3A CN112105665A (zh) | 2018-03-23 | 2019-03-21 | 延长适用期的用于低温固化的聚脲二酮树脂 |
Applications Claiming Priority (30)
Application Number | Priority Date | Filing Date | Title |
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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 | ||
EP18181877.4 | 2018-07-05 | ||
EP18181876.6A EP3590987A1 (fr) | 2018-07-05 | 2018-07-05 | Compositions aqueuses contenant des groupes urétdione et leur procédé de production |
EP18181877.4A EP3590988A1 (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 |
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 |
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 |
PCT/EP2019/057069 WO2019180131A1 (fr) | 2018-03-23 | 2019-03-21 | Compositions aqueuses contenant des groupes uretdione et procédé pour leur préparation |
PCT/EP2019/057066 WO2019180129A1 (fr) | 2018-03-23 | 2019-03-21 | Système catalytique pour dispersions d'uretdione |
PCT/US2019/023292 WO2019183305A1 (fr) | 2018-03-23 | 2019-03-21 | Durcissement amélioré de compositions de polyallophanate par neutralisation de l'acide de sous-couche |
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PCT/EP2019/057068 WO2019180130A1 (fr) | 2018-03-23 | 2019-03-21 | Dispersions de polyuréthane contenant de l'urétdione comprenant des groupes hydrophiles |
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 |
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 |
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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 |
PCT/EP2019/057069 WO2019180131A1 (fr) | 2018-03-23 | 2019-03-21 | Compositions aqueuses contenant des groupes uretdione et procédé pour leur préparation |
PCT/EP2019/057066 WO2019180129A1 (fr) | 2018-03-23 | 2019-03-21 | Système catalytique pour dispersions d'uretdione |
PCT/US2019/023292 WO2019183305A1 (fr) | 2018-03-23 | 2019-03-21 | Durcissement amélioré de compositions de polyallophanate par neutralisation de l'acide de sous-couche |
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CN (10) | CN111886273A (fr) |
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CN110698622A (zh) * | 2019-10-12 | 2020-01-17 | 北京长润化工有限公司 | 酮亚胺潜伏固化剂和具有其的反应型聚氨酯热熔胶及应用 |
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EP2993202A1 (fr) * | 2014-09-08 | 2016-03-09 | Evonik Degussa GmbH | Demi-produits composites et pièces moulées en étant constituées ainsi que pièces moulées directement fabriquées à base de (méth)acrylates hydroxyfonctionnalisés et d'uretdions réticulés par duroplastie |
EP3026071A1 (fr) * | 2014-11-26 | 2016-06-01 | Henkel AG & Co. KGaA | Dispersions de polyuréthane stabilisées |
CN107683297B (zh) * | 2015-05-29 | 2020-09-08 | 巴斯夫欧洲公司 | 用于纤维复合材料的具有较长开放时间的聚氨酯-聚异氰脲酸酯树脂 |
CN108699204B (zh) * | 2016-03-09 | 2020-10-16 | 旭化成株式会社 | 多异氰酸酯组合物、涂覆组合物、水系涂覆组合物和涂覆基材 |
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2019
- 2019-03-21 EP EP19713668.2A patent/EP3768756A1/fr active Pending
- 2019-03-21 CN CN201980021448.2A patent/CN111886273A/zh active Pending
- 2019-03-21 EP EP19711129.7A patent/EP3768751A1/fr active Pending
- 2019-03-21 EP EP19713663.3A patent/EP3768747A1/fr not_active Withdrawn
- 2019-03-21 WO PCT/EP2019/057068 patent/WO2019180130A1/fr active Application Filing
- 2019-03-21 CN CN201980034098.3A patent/CN112105665A/zh active Pending
- 2019-03-21 WO PCT/US2019/023319 patent/WO2019183319A1/fr active Application Filing
- 2019-03-21 EP EP19711125.5A patent/EP3768749A1/fr active Pending
- 2019-03-21 WO PCT/EP2019/057065 patent/WO2019180128A1/fr active Application Filing
- 2019-03-21 EP EP19713670.8A patent/EP3768758A1/fr not_active Withdrawn
- 2019-03-21 EP EP19713667.4A patent/EP3768755A1/fr not_active Withdrawn
- 2019-03-21 WO PCT/US2019/023325 patent/WO2019183323A1/fr active Application Filing
- 2019-03-21 EP EP19711128.9A patent/EP3768745A1/fr not_active Withdrawn
- 2019-03-21 WO PCT/US2019/023334 patent/WO2019183330A1/fr active Application Filing
- 2019-03-21 WO PCT/US2019/023299 patent/WO2019183308A1/fr active Application Filing
- 2019-03-21 EP EP19713339.0A patent/EP3768752A1/fr active Pending
- 2019-03-21 WO PCT/US2019/023312 patent/WO2019183313A1/fr active Application Filing
- 2019-03-21 EP EP19711127.1A patent/EP3768748A1/fr not_active Withdrawn
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- 2019-03-21 CN CN201980021604.5A patent/CN112004853B/zh active Active
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- 2019-03-21 CN CN201980021447.8A patent/CN111886271A/zh active Pending
- 2019-03-21 WO PCT/US2019/023297 patent/WO2019183307A1/fr active Application Filing
- 2019-03-21 CN CN201980021445.9A patent/CN111886272B/zh active Active
- 2019-03-21 EP EP19713666.6A patent/EP3768754A1/fr not_active Withdrawn
- 2019-03-21 WO PCT/US2019/023314 patent/WO2019183315A1/fr active Application Filing
- 2019-03-21 WO PCT/EP2019/057064 patent/WO2019180127A1/fr active Application Filing
- 2019-03-21 CN CN201980021630.8A patent/CN111868131A/zh active Pending
- 2019-03-21 EP EP19713665.8A patent/EP3768753A1/fr not_active Withdrawn
- 2019-03-21 WO PCT/EP2019/057069 patent/WO2019180131A1/fr active Application Filing
- 2019-03-21 WO PCT/EP2019/057066 patent/WO2019180129A1/fr active Application Filing
- 2019-03-21 EP EP19711126.3A patent/EP3768750A1/fr active Pending
- 2019-03-21 CN CN201980034350.0A patent/CN112105666B/zh active Active
- 2019-03-21 EP EP19713669.0A patent/EP3768757A1/fr not_active Withdrawn
- 2019-03-21 EP EP19714972.7A patent/EP3768759A1/fr not_active Withdrawn
- 2019-03-21 CN CN201980021508.0A patent/CN112041367B/zh active Active
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