WO2017132089A1 - Compositions de marquage de trafic contenant des amines polyfonctionnelles - Google Patents

Compositions de marquage de trafic contenant des amines polyfonctionnelles Download PDF

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WO2017132089A1
WO2017132089A1 PCT/US2017/014546 US2017014546W WO2017132089A1 WO 2017132089 A1 WO2017132089 A1 WO 2017132089A1 US 2017014546 W US2017014546 W US 2017014546W WO 2017132089 A1 WO2017132089 A1 WO 2017132089A1
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Prior art keywords
paint
aqueous latex
agents
latex paint
added
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Kevin NEWELL
Haibo Li
Jeremy CHEEK
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Ennis Flint Inc
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Ennis Paint Inc
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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
    • C09D179/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09D161/00 - C09D177/00
    • C09D179/02—Polyamines
    • 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
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/02—Polyamines
    • C08G73/0273—Polyamines containing heterocyclic moieties in the main chain
    • 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
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/0622—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms
    • C08G73/0633—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms with only two nitrogen atoms in the ring
    • 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
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/0622—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms
    • C08G73/0638—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms with at least three nitrogen atoms in the ring
    • 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
    • C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
    • 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
    • C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
    • C09D133/02—Homopolymers or copolymers of acids; Metal or ammonium salts thereof
    • 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
    • C09D179/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09D161/00 - C09D177/00
    • C09D179/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
    • 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
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/004—Reflecting paints; Signal paints
    • 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
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/02—Emulsion paints including aerosols
    • C09D5/022—Emulsions, e.g. oil in water
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2201/00—Properties
    • C08L2201/54—Aqueous solutions or dispersions

Definitions

  • aqueous coating compositions containing an anionically stabilized polymer, one or more polyfunctional amines, and a volatile base.
  • Coating compositions can further include one or more additional copolymers, which may or may not be anionically stabilized, and/or additional additives, including pigments, defoamers, pigment dispersing agents, thickeners, surfactants, and combinations thereof.
  • the setting time (and drying time) of the coating compositions can be decreased. Also provided are coatings formed from the coating compositions described herein, as well as methods of forming these coatings.
  • the present disclosure relates generally to fast-drying coating compositions containing polyfunctional amines for use in a variety of applications.
  • Disclosed are fast drying aqueous coating compositions comprising; an anionically stabilized copolymer, a polyfunctional amine, and a volatile base exhibiting improved early water (water wash-off) resistance. These coatings exhibit fast drying times upon application to a surface.
  • the coating compositions display suitable physical properties for a wide variety of exterior coating/paint applications.
  • the coating compositions contain one or more anionically stabilized polymers.
  • the coating compositions also contain a polyfunctional amine, such as those comprising recurring units derived from the reaction of one tri-glycidyl moiety and a single di-, or tri-functional amino monomers, or combination of mono/bi, mono/tri, mono/tetra, bi/bi, bi/tri, bi/tetra, tri/tri, tri/tetra, and tetra/tetra functional amino monomers with a bi- or tri-glycidyl moiety, or a combination thereof.
  • Suitable polyfunctional amines can possess a variety of molecular weights and degrees of nitrogen-derivatization.
  • the polyfunctional amine can have an average molecular weight of between 100 and 500,000 Daltons and/or a degree of nitrogen- derealization between 5% and 100%.
  • the polyfunctional amine is present in the coating composition at between 0.1% by weight and 2.5% by solid weight of the polyfunctional amine to the total weight of the coating/paint formulae.
  • the coating compositions also contain a volatile base.
  • volatile bases include, but are not limited to, ammonia, lower alkylamines such as dimethylamine and diethylamine, ethanolamine, morpholine, aminopropanol, 2-amino-2-methyl-l-propanol, 2- dimethylaminoethanol, and combinations thereof.
  • the volatile base is ammonia.
  • Coating compositions can further contain an additional polymer.
  • the additional polymer can be, for example, a polymer or copolymer derived from one or more (meth)acrylate monomers, vinyl aromatic monomers, ethylenically unsaturated aliphatic monomers, vinyl ester monomers, and combinations thereof.
  • the coating compositions can also include one or more additives, including pigments, fillers, dispersants, coalescents, pH neutralizing agents, plasticizers, defoamers, surfactants, thickeners, biocides, co-solvents, and combinations thereof.
  • coatings formed from the coating compositions described herein, as well as methods of forming these coatings and/or paints are formed by applying a coating composition described herein to a surface, and allowing the coating to dry to form a coating.
  • the resultant dry coatings typically comprise, at minimum, an anionically stabilized polymer and a polyfunctional amine.
  • the dry coatings can further comprise one or more additional polymers and/or additives as described above.
  • the coating thickness can vary depending upon the application of the coating. In some embodiments, the coating has a dry thickness of between 5 mils and 20 mils. In general, the coating must have a change in viscosity, provided as a change in Krebs Units (AKU) of 10 KU or less after being placed in an oven for 14 days, according to the ASTM D-562 standard.
  • AKU Krebs Units
  • the coating compositions can be applied to a variety of surfaces including, but not limited to metal, asphalt, concrete, stone, ceramic, wood, plastic, polymer, polyurethane foam, glass, and combinations thereof.
  • the preferred surfaces of this disclosure are those used in roadway paving and surfacing.
  • the coating compositions can be applied to interior or exterior surfaces.
  • (meth)acrylate monomer includes aery late, methacrylate, diacrylate, and dimethacrylate monomers.
  • the coating compositions described herein contain one or more anionically stabilized polymers.
  • the anionically stabilized polymer includes an acrylic-based copolymer.
  • the acrylic-based copolymer is derived from two or more, three or more, or four or more (meth)acrylate monomers.
  • the acrylic-based copolymer is derived from one or more (meth)acrylate monomers selected from the group consisting of methyl methacrylate, butyl acrylate, 2-ethylhexylacrylate, and combinations thereof.
  • the emulsion polymerization can be carried out as a batch process, as a semi-batch process, or in the form of a continuous process.
  • a portion of the monomers can be heated to the polymerization temperature and partially polymerized, and the remainder of the monomer batch can be subsequently fed to the polymerization zone continuously, in steps, or with superposition of a concentration gradient.
  • the copolymer is produced in a single stage (i.e., does not include separate feeds having different monomer compositions so as to produce a multistage polymer particle such as a core/shell particle).
  • the emulsion polymerization can be performed with a variety of auxiliaries, including water- soluble initiators and regulators. Reduction-oxidation (redox) initiator systems are also suitable as initiators for the emulsion polymerization.
  • Dispersants such as surfactants, can also be added during polymerization to help maintain the dispersion of the monomers in the aqueous medium.
  • Anionic and nonionic surfactants can be used during polymerization.
  • the coating compositions described herein further contain one or more poly functional amines.
  • the poly functional amine functions as a fast drying agent and decreases the setting time of the coating compositions.
  • Polyfunctional amines are compounds which contain a plurality of primary amine groups, secondary amine groups, or combinations thereof.
  • the polyfunctional amine contains at least three primary amine groups, secondary amine groups, or combinations thereof.
  • the polyfunctional amine can be a polymer or copolymer derived from one or more monomers containing an amine group.
  • the polyfunctional amine is an acrylic polymer derived from one or more monomers comprising an amino group.
  • Polyfunctional amines, as described herein are polyamines that are N-derivatized such that one or more amine nitrogens have been derivatized (i.e., some number of the primary and/or secondary amine groups within the polyamine have been covalently modified to replace one or more hydrogen atoms in the primary and/or secondary amine groups with a non-hydrogen moiety).
  • polyfunctional amines can include polyamines where at least a portion of the primary amine groups have been converted to either secondary or tertiary amine groups.
  • polyfunctional amines can include polyamines where at least a portion of the secondary amine groups have been converted to tertiary amines.
  • Suitable polyfunctional amines are known in the art, and include polyamines in which some number of the primary and/or secondary amine groups have been covalently modified to replace one or more hydrogen atoms with a non-hydrogen moiety (R).
  • the R groups present within a polyfunctional amine can be selected such that the polyfunctional amine possesses a hydrophilicity which renders the polyfunctional amine compatible with the aqueous compositions described herein.
  • the R groups within the polyfunctional amine can be selected such that the polyfunctional amine is water soluble or water dispersible.
  • Polyfunctional amines are generally incorporated into the compositions in amounts less than 10% by weight, based on the dry weight of the anionically stabilized copolymer.
  • the amount of polyfunctional amine present in the composition can be selected in view of the identity of the polyfunctional amine, the nature of the anionically stabilized copolymer present in the composition, and the desired setting time of the composition.
  • the polyfunctional amine is present in the composition at between 0.1% by weight and 5% by weight, based on the dry weight of the anionically stabilized copolymer. In certain embodiments, the polyfunctional amine is present in the composition at between 0.5% by weight and 2.5% by weight, based on the dry weight of the anionically stabilized copolymer.
  • Polyfunctional amines having a range of molecular weights and degrees of nitrogen- derivatization can be incorporated into the coating compositions.
  • the setting time of the composition, as well as the physical properties of the resultant coating can be varied by selection of the loading level, molecular weight, microstructure (e.g., degree of branching), and the degree of nitrogen-derivatization of the polyfunctional amine.
  • the setting time of the composition, as well as the physical properties of the resultant coating can also be influenced by ambient conditions during coating application and drying, including humidity and temperature.
  • a particular polyfunctional amine is incorporated into the coating composition at a particular loading level in view of ambient conditions, including humidity and temperature, to achieve a coating having a desired setting time, desired physical properties, or a combination thereof.
  • the polyfunctional amines have a weight average molecular weight of varying from about 100 to 500,000 Daltons; more preferably from 500 to 100,000 and most preferably from 1 ,000 to 20,000. Since the polymers of the present invention become highly crosslinked upon drying, there is no substantial disadvantage to starting with very low molecular weight polymers.
  • the fast drying coating compositions described herein also contain a volatile base.
  • Volatile bases are basic substances that are soluble in water, remain in the aqueous coating composition under normal storage conditions, and evaporate from the aqueous coating composition under suitable drying conditions.
  • one or more volatile bases are incorporated in the composition in an effective amount to maintain the pH of the coating composition in the range of from 7.5 to 12.5 or in the range from 9 to 1 1. In some embodiments, one or more volatile bases are incorporated in the composition at between 0.1% by weight and 5.0% by weight. In certain embodiments, one or more volatile bases are incorporated in the composition at between 0.5% by weight and 2.5% by weight.
  • Suitable volatile bases can be selected on the basis of several factors, including their basicity and volatility.
  • Exemplary volatile bases include, but are not limited to, ammonia, lower alkylamines such as dimethylamine, triethylamine, and diethylamine, ethanolamine, diethanolamine, triethanolamine, morpholine, aminopropanol, 2-amino-2-methyl-l -propanol, 2-dimethylaminoethanol, and combinations thereof.
  • the volatile base is ammonia.
  • ammonia is the sole volatile base present in the coating composition.
  • ammonia can be incorporated in admixture with other volatile bases, non-volatile bases, such as alkali metal hydroxides, or combinations thereof.
  • the aqueous coating compositions can further include one or more additives, including pigments, fillers, dispersants, coalescents, pH modifying agents, plasticizers, defoamers, surfactants, thickeners, biocides, co-solvents, and combinations thereof.
  • additives including pigments, fillers, dispersants, coalescents, pH modifying agents, plasticizers, defoamers, surfactants, thickeners, biocides, co-solvents, and combinations thereof.
  • additives including pigments, fillers, dispersants, coalescents, pH modifying agents, plasticizers, defoamers, surfactants, thickeners, biocides, co-solvents, and combinations thereof.
  • Suitable additives that can optionally be incorporated into the composition include rheology modifiers, wetting and spreading agents, leveling agents, conductivity additives, adhesion promoters, anti-blocking agents, anti-cratering agents and anti-crawling agents, anti- freezing agents, corrosion inhibitors, anti-static agents, flame retardants and intumescent additives, dyes, optical brighteners and fluorescent additives, UV absorbers and light stabilizers, chelating agents, cleanability additives, crosslinking agents, flatting agents, flocculants, humectants, insecticides, lubricants, odorants, oils, waxes and slip aids, soil repellants, stain resisting agents, and combinations thereof.
  • the coating compositions described above can be provided as aqueous dispersions having a volume solids content of from 45 - 65% or from 60-77% by weight of the total paint formulation.
  • coatings formed from the coating compositions described herein are formed by applying a coating composition described herein to a surface, and allowing the coating to dry to form a coating.
  • the resultant dry coatings typically comprise, at minimum, an anionically stabilized polymer and a polyfunctional amine.
  • the dry coatings can further comprise one or more additives (e.g., pigments and/or fillers) as described above.
  • Coating compositions can be applied to a surface by any suitable coating technique, including spraying, rolling, brushing, or spreading. Coating compositions can be applied in a single coat, or in multiple sequential coats (e.g., in two coats or in three coats) as required for a particular application. Generally, the coating composition is allowed to dry under ambient conditions. However, in certain embodiments, the coating composition can be dried, for example, by heating and/or by circulating air over the coating.
  • Coating thickness can vary depending upon the application of the coating.
  • the coating compositions can be applied to a variety of surfaces including, but not limited to metal, asphalt, concrete, stone, ceramic, wood, plastic, polyurethane foam, glass, and combinations thereof.
  • the coating compositions can be applied to interior or exterior surfaces.
  • the coating is applied to a surface to reflect solar radiation.
  • the coating will generally contain one or more pigments that reflect solar energy, such as titanium dioxide. By reflecting the sun's heat, the coating can help to cool a surface.
  • the roof coating can help to reduce a building's interior temperatures and cooling costs.
  • the coating is applied to a road surface as traffic paint.
  • the road surface can be, for example, asphalt or concrete.
  • the coating contains a filler such as a reflective filler.
  • Polyfunctional amines can also be incorporated as fast drying agents in other types of compositions which contain anionically stabilized copolymers.
  • polyfunctional amines may be utilized to decrease the setting time of other compositions where fast setting and/or rain resistance are desirable.
  • an aqueous coating composition (that may be an aqueous latex paint) comprising: (a) one or more anionically stabilized acrylic copolymer;
  • the polyfunctional amines may further include one or more variations of structures I-x-1 and I-x-2' provided as I-x-1 ' and I-x-2" so that a final polyfunctional amine structure is partially or fully saturated and/or highly branched wherein: ( ⁇ - ⁇ - ⁇ ')
  • n is a number between 1 and 100, and where M n is 5,000 to 20,000 Daltons.
  • the aqueous latex paint provides for dry times on paved surfaces in an atmosphere that is characterized as possessing at least 50% and up to 75% relative humidity with a final AKu value of no greater than 10.0, as measured using ASTM D711.
  • the aqueous latex paint provides for water resistance that reduces or eliminates blistering, wherein the aqueous latex paint is tested according to ASTM D870 for water immersion.
  • the latex paint provides for water resistance that improves scrub resistance as compared to said aqueous latex paint with commercially available quick drying agents (CQDA's) by at least 30 % wherein the paint is tested according to ASTM D 2486 for water immersion.
  • CQDA's commercially available quick drying agents
  • the latex paint provides for water resistance that improves color fastness by improving opacity to at least 98 % as compared to aqueous latex paint with commercially available quick drying agents (CQDA's) wherein the paint is tested according to ASTM D 2850 for color opacity.
  • CQDA's commercially available quick drying agents
  • the aqueous latex paint may contain only white pigment or yellow pigment.
  • the aqueous latex paint contains polyfunctional amines having average molecular weights of between 100 and 500,000 Daltons and more preferably an average molecular weight of between 5,000 and 20,000 Daltons.
  • the aqueous latex composition may be present in the paint at between 0.1% by weight and 5% by weight, based on a dry weight of an anionically stabilized copolymer.
  • the aqueous latex paint may be present at between 0.5% by weight and 2.5% by weight, based on a dry weight of the anionically stabilized copolymer.
  • the aqueous latex paint may be comprised of one or more additional polymers and the paint may include additional pigments, fillers, dispersants, coalescents, pH modifying agents, plasticizers, defoamers, surfactants, thickeners, biocides, co-solvents, and combinations thereof.
  • Additional additives integrated into the paint may include rheology modifiers, wetting and spreading agents, leveling agents, conductivity additives, adhesion promoters, anti-blocking agents, anti-cratering agents and anti-crawling agents, anti-freezing agents, corrosion inhibitors, anti-static agents, flame retardants and intumescent additives, dyes, optical brighteners and fluorescent additives, UV absorbers and light stabilizers, chelating agents, cleanability additives, crosslinking agents, flatting agents, flocculants, humectants, insecticides, lubricants, odorants, oils, waxes and slip aids, soil repellants, stain resisting agents, and combinations thereof.
  • the aqueous latex paint may include aqueous dispersions having a volume solids content of between 45 and 65% by weight of a total paint formulation.
  • the aqueous latex paint may more preferably include aqueous dispersions having a volume solids content of between 60 and 77% by weight of a total paint formulation.
  • the coating compositions may be applied to a surface selected from the group consisting of metal, asphalt, concrete, stone, ceramic, wood, plastic, polyurethane foam, glass, and combinations thereof.
  • the coating compositions may have a dry coating (often a film) thickness of between 10 mils and 100 mils.
  • a dry coating of between 10 mils and 100 mils.
  • the mixture is added to the first vessel while stirring with a high sheer mixing blade at a moderate speed for at least 5 minutes and; (iv) adding to the first vessel a rheology modifier and water and stirring an overall mixture at high speed for at least another 5 minutes and
  • compositions containing polyfunctional amine crosslinkers as fast drying agents in latex compositions are provided herein.
  • these formulations are preferably used as traffic markings or roadway markings with the colors white and yellow provided. The selection of these specific colored embodiments in no way are suggested as a limitation of the disclosure.
  • Acrylic latex compositions containing a polyfunctional amine crosslinker as a fast-drying additive for white marking compositions are given as provided in Table 1.
  • Elastomeric coatings (white and yellow are the preferred colors obtained primarily by using inorganic pigments, but other colors are possible as well) containing at least one anionically stabilized acrylic-based copolymer and at least one polyfunctional amine with the structures (I-x-1) and ( ⁇ - ⁇ -2') and modifications thereof (as shown below) are described.
  • a commercially available quick drying agent such as a polyfunctional amine that is a known alkoxylated polyalkyleneimine was also prepared as a basis for comparison.
  • Examples 1-4 provide details of these coating formulations for producing white pigmented compositions.
  • Examples 5-8 provide details of these coating formulations for producing yellow pigmented compositions.
  • I-x-1 and I-x-2' structures include variations, provided as I-x-1 ' and I-x-2" below indicating that the final polyfunctional amine can be partially or fully saturated and/or highly branched:
  • R H or the next repeating unit and where the next repeating unit is represented as (I-x-1 '-RU) (I-x-l'-RU)
  • n is equal to a number 1 to 100
  • pigments and fillers including 140 lb Titanium dioxide, 510.0 lb Calcium carbonate, and 150 lb silica were added carefully while stirring at high speed for an additional 15 minutes.
  • 35 lb of a solvent methyl alcohol in this case although other alcohols and ketones could be substituted
  • 20.0 lb of a coalescent solvent such as 2,2,4-Trimethyl-l ,3-pentanediol monoisobutyrate was added to the mixture, while stirring continued.
  • a white paint composition containing a poly functional amine of the (I-x-1) structure shown was provided by adding 458.0 lb of in-house aqueous polymer emulsion, also referred to as EF Acrylic Latex 1 to a vessel to which was added 11 lb of the polyfunctional amine crosslinker (1-x-l) and stirred for 5 minutes using a high sheer mixing blade at moderate speed.
  • Example 2 In an identical manner as described in Example 1 above, while mixing this solution, 7.0 lb defoamer, 5.0 lb octylphenol ethoxylate nonionic surfactant, 8 lb of a high performance dispersant polymer combination, 0.2 lb biocide, and 0.3 lb thickener was pre-mixed with 11.3 lb of water and subsequently added to the Latex 1 emulsion with the (I-x-1) crosslinker and allowed to continue stirring with a high sheer mixing blade at a moderate speed for another 5 minutes. To this, approximately 10 lb ammonia, or more was added to obtain a solution of pH 10.
  • pigments and fillers including 140 lb titanium dioxide, 510 lb calcium carbonate, and 150 lb silica were added carefully while stirring at high speed for 15 minutes. After completion of the mixing and accompanying grinding, 35 lb of the solvent as described in Example 1 was added slowly and at reduced stirring speed together with 3.0 lb propylene glycol and 10 lb of a waterbome float solution intermediate. Then 10 g glycol ether solvent and 10 lb of a coalescent solvent such as 2,2,4-Trimethyl-l ,3-pentanediol monoisobutyrate, were added to the mixture and this mixture was allowed to continuously stir.
  • EXAMPLE 3 EXAMPLE 3 :
  • a white paint composition containing a polyfunctional amine of the ( ⁇ - ⁇ -2') structure shown was provided by adding 458.0 lb of in-house aqueous polymer emulsion, also referred to as EF Acrylic Latex 1 to a vessel to which was added 11 lb of the polyfunctional amine crosslinker (1- ⁇ -2') and stirred for 5 minutes using a high sheer mixing blade at moderate speed.
  • a white paint composition containing a commercially available quick drying agent (CQDA) was provided by adding 458.0 lb of in-house aqueous polymer emulsion, also referred to as EF Acrylic Latex 1 to a vessel to which was added 11 lb of the commercially available quick drying agent (CQDA) and stirred for 5 minutes using a high sheer mixing blade at moderate speed.
  • CQDA commercially available quick drying agent
  • Table 1 provided below summarizes the four different white paint (coating) compositions described above.
  • Paint viscosity is determined by measuring Krebs Units (Ku) using a paddle type viscometer according to ASTM D562. Viscosities of 80 to 90 Ku are considered suitable for testing. When the formulation(s) was complete, the off the mill (OTM) viscosity (KU) and pH of the paints were measured and recorded. The formulation KU and pH was retested after being allowed to sit overnight.
  • OTM off the mill
  • the change in Krebs Units should be less than or equal to 10 Ku and preferably less than 7 Ku, when measured per ASTM-562, entitled "Standard Test Method for Consistency of Paints Measuring Krebs Unit (KU) Using a Stormer-Type Viscometer".
  • a ⁇ of greater than 10 Ku is considered a formulation failure and the coating is not viable for commercial use for traffic paint compositions.
  • OTM off-the-mill
  • a non-ionic, water soluble hydroxyethyl cellulose thickener can be added to raise the viscosity to within the suitable range for testing.
  • An example thickener is Natrosol HBR 250.
  • Example 1 presented an insufficient initial viscosity measurement and was allowed to sit overnight in order to allow for complete activation of the thickener and equilibration of the formulation.
  • the overnight Ku was measured at 80.6 with a pH of 10.34.
  • 0.15 g thickener was added to increase the viscosity to within the measurable range of 80-90 Ku.
  • Viscosity was measured after the addition of thickener at 82.2 Ku.
  • the formulation was again allowed to sit ovemight where the viscosity was again measured and determined to be 83.20 Ku with a pH of 10.34. After a 2 week period of heat stability, the final Ku was measured at 139.70.
  • the composition containing an anionically stabilized acrylic- based copolymer and a polyfunctional amine of Structure ( ⁇ - ⁇ -2'), (Example 3) exhibited a AKu of 0.8 with a dry time according to ASTM standard D711 of 8 minutes, and with a 75% humidity dry time of 11 minutes.
  • the addition of I-x-2' in the latex improved the water resistance and dry time of the coatings with compositions containing 11 lbs/100 gallons of (I- x-2') and was suitable for road pavement paint.
  • Drawdown samples were prepared via the procedure provided herein: A sample of paint was drawn to 15 mil wet film thickness onto to a clean black scrub test panel and allowed to dry horizontally for 30 to 60 minutes at ambient temperature and 50 to 55% relative humidity. When the drying time is complete, the samples were placed vertically into a vessel of 72°F ⁇ 2°F still tap water and allowed to remain there for 30 minutes, during which time the film is observed for effects of water damage and times of noted damage is recorded. After completion of the test, the samples were then removed from the water and further observed noting the percentage of wash off erosion, percentage of blistering of area exposed to water during test, and size of the blisters (Small ⁇ 5mm, Medium 5-10 mm, Large > 10mm). Recovery of blistering is measured as Pass/Fail. Pass was determined as a complete recovery of blistering after drying of the sample. Failure was determined if the film still showed effects of blistering after complete drying of the sample.
  • Example 1 was not a viable formulation and therefore was not suitable for further testing which is the reason that no further test results are provided. Within Table 4, only Example 2 passed the test. Example 3 and 4 exhibited delamination of the paint from the substrate.
  • Table 4 Water Immersion Performance of Compositions Containing Polyfunctional Amine Crosslinkers as a Fast Drying Agent (White) - All numbers in Table 4 correspond to minutes and seconds prior to inspection and determination
  • the color performance data of the viable white compositions containing polyfunctional amine crosslinkers of the present disclosure were tested according to ASTM D2805-96a, "Standard Test Method for Hiding Power of Paints by Reflectometry", are provided in Table 6.
  • the acceptable range of opacity according to the standard is between 77.16% and 99.00%.
  • Example 1 provided no testable final formulation and therefore no results were obtained.
  • a quart can containing 445.0 lb of in-house aqueous polymer emulsion, also referred to as EF Acrylic Latex 1 with an addition of 11 lb of the polyfunctional amine crosslinker ( ⁇ - ⁇ -2'), and stirred for 5 minutes using a high sheer mixing blade at moderate speed.
  • EF Acrylic Latex 1 with an addition of 11 lb of the polyfunctional amine crosslinker ( ⁇ - ⁇ -2')
  • ⁇ - ⁇ -2' polyfunctional amine crosslinker
  • EXAMPLE 6 To produce a yellow paint composition containing a commercially available quick drying agent (CQDA) a quart can containing 445.0 lb of in-house aqueous polymer emulsion, also referred to as EF Acrylic Latex 1 with an addition of 1 1 lb of the CDQA and stirred for 5 minutes using a high sheer mixing blade at moderate speed. Next, 6.0 lb defoamer, 6 lb. poly carboxy lie acid dispersant, 0.13 lb thickener, 5 lb grind aid surfactant, and 4 lb. amine alkoxylated stabilizing surfactant dispersion were added while stirring the Latex/CDQA mixture with a high sheer mixing blade at a moderate speed for another 5 minutes.
  • CQDA quick drying agent
  • 9.79 lb of water was added to the stirring mixture and stirred at high speed for another 5 minutes.
  • approximately 3.5 lb ammonia was added to obtain a solution of pH 10.
  • pigments and fillers including 23 lb Titanium dioxide, 560.0 lb Calcium carbonate, 24.6 lb organic yellow pigment, 1.5 lb yellow iron oxide, and 170 lb silica were added carefully while stirring at high speed for 15 minutes.
  • Formulations for yellow pigmented paint Examples 5-8 are summarized in Table 7 below: Table 7; Compositions Containing a Polyfunctional Amine Crosslinker as a Fast Drying Agent (Yellow) - All numbers correspond to weight in pounds of each additive
  • OTM off-the-mill
  • Example 7 had an Overnight Ku measurement of 70.5 Ku.
  • the Ovemight pH was measured at 9.63.
  • 0.50g thickener was added to increase the viscosity to within the measurable range of 80-90 Ku.
  • the OTM Ku was measured again as 83.5 Ku. No further viscosity adjustment was needed and after a 2 week period of heat stability, the final Ku was measured at 81.3 Ku.
  • composition containing an anionically stabilized acrylic-based copolymer and a polyfunctional amine of Structure ( ⁇ - ⁇ -2'), (Example 8) exhibited AKu of - 1.8 with a dry time according to ASTM standard D71 1 of 5 minutes, with a 75% humidity dry time of 12 minutes.
  • Table 9 summarizes the dry time test results for Examples 5-8 for yellow paint.
  • the color performance data of the viable yellow compositions containing a polyfunctional amine crosslinker of the disclosure according to ASTM D2805-96a, "Standard Test Method for Hiding Power of Paints by Reflectometry", are provided in Table 11.
  • the acceptable range of opacity according to the standard is 77.16% to 99.00%.
  • compositions and methods of the appended claims are not limited in scope by the specific compositions and methods described herein, which are intended as illustrations of a few aspects of the claims and any compositions and methods that are functionally equivalent are intended to fall within the scope of the claims.
  • compositions and method steps disclosed herein are specifically described, other combinations of the compositions and method steps also are intended to fall within the scope of the appended claims, even if not specifically recited.
  • a combination of steps, elements, components, or constituents may be explicitly mentioned herein as well as combinations of steps, elements, components, and constituents are included though not explicitly stated.
  • the term "comprising" and variations thereof as used herein is used synonymously with the term “including” and variations thereof and are open, non-limiting terms.

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Abstract

La présente invention concerne des compositions de revêtement aqueuses contenant un polymère anioniquement stabilisé, une ou plusieurs amines polyfunctionnelles comme agents de réticulation, et une base volatile. Les compositions de revêtement peuvent en outre comprendre un ou plusieurs copolymères additionnels, qui peuvent ou pas être anioniquement stabilisés, et/ou des additifs additionnels, comprenant des pigments, des agents de démoussage, des agents de dispersion de pigment, des épaississants, des tensioactifs, et des combinaisons de ces derniers. En incorporant une ou plusieurs amines polyfunctionnelles, telles que celles comprenant des motifs de répétition dérivés de la réaction d'une fraction tri-glycidylique et d'un monomère amino di-, ou tri-fonctionnel unique, ou une combinaison de monomères amino mono/bi, mono/tri, mono/tétra, bi/bi, bi/tri, bi/tétra, tri/tri, tri/tétra, et tétra/tétra fonctionnels avec une fraction bi- ou tri-glycidylique, la résistance au lavage à l'eau des compositions de revêtement qui comprennent des formulations de peinture, peut être accrue.
PCT/US2017/014546 2016-01-29 2017-01-23 Compositions de marquage de trafic contenant des amines polyfonctionnelles Ceased WO2017132089A1 (fr)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108727960A (zh) * 2018-06-13 2018-11-02 合肥仁德电子科技有限公司 一种用于手机外壳的防水涂料及其制备方法
US20220033638A1 (en) * 2018-09-26 2022-02-03 Lubrizol Advanced Materials, Inc. Fast Drying Waterborne Coatings

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5527853A (en) * 1989-07-21 1996-06-18 Rohm And Haas Company Shelf stable fast-cure aqueous coating
US20150259562A1 (en) * 2013-03-15 2015-09-17 Ennis Paint, Inc Controlled Crosslinking of Latex Polymers With Polyfunctional Amines

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5527853A (en) * 1989-07-21 1996-06-18 Rohm And Haas Company Shelf stable fast-cure aqueous coating
US20150259562A1 (en) * 2013-03-15 2015-09-17 Ennis Paint, Inc Controlled Crosslinking of Latex Polymers With Polyfunctional Amines

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108727960A (zh) * 2018-06-13 2018-11-02 合肥仁德电子科技有限公司 一种用于手机外壳的防水涂料及其制备方法
US20220033638A1 (en) * 2018-09-26 2022-02-03 Lubrizol Advanced Materials, Inc. Fast Drying Waterborne Coatings

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