WO2023072128A1 - Composition colorante et article revêtu - Google Patents

Composition colorante et article revêtu Download PDF

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Publication number
WO2023072128A1
WO2023072128A1 PCT/CN2022/127604 CN2022127604W WO2023072128A1 WO 2023072128 A1 WO2023072128 A1 WO 2023072128A1 CN 2022127604 W CN2022127604 W CN 2022127604W WO 2023072128 A1 WO2023072128 A1 WO 2023072128A1
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Prior art keywords
meth
ethylenically unsaturated
unsaturated monomer
water
component
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PCT/CN2022/127604
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English (en)
Inventor
Naiwo YU
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Guangdong Huarun Paints Co., Ltd.
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Application filed by Guangdong Huarun Paints Co., Ltd. filed Critical Guangdong Huarun Paints Co., Ltd.
Publication of WO2023072128A1 publication Critical patent/WO2023072128A1/fr

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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
    • 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
    • C09D15/00—Woodstains
    • 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
    • C09D133/04—Homopolymers or copolymers of esters
    • C09D133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C09D133/08—Homopolymers or copolymers of acrylic acid esters
    • 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
    • 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
    • C09D5/002—Priming 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
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/65—Additives macromolecular
    • 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
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/66—Additives characterised by particle size
    • C09D7/67—Particle size smaller than 100 nm
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2205/00—Polymer mixtures characterised by other features
    • C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
    • C08L2205/025—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group containing two or more polymers of the same hierarchy C08L, and differing only in parameters such as density, comonomer content, molecular weight, structure

Definitions

  • the present application relates to a colorant composition and a coated article. Specifically, the present application relates to a colorant composition for a porous substrate, and a coated article comprising a coating formed by the colorant composition.
  • Colorants are often applied to porous substrates (such as wood) and can be used, for example, to provide color while allowing an appearance to transparently exhibit natural color and texture of some substrates.
  • porous substrates such as wood
  • colorants for wood there are two basic types of colorants for wood, including water-based and oil-based colorants.
  • water-based colorants are attracting more and more attention.
  • researchers have been trying to develop some water-based colorants.
  • the existing water-based colorants still have many shortcomings during the application process, such as poor wipeability (the ability for application in wipe-coating) , poor entry into conduit (or vessel) , uneven and non-vivid colors, slow drying speed and poor adhesion.
  • water-based acrylic emulsion system or water-based alkyd system are mainly used in most water-based colorants.
  • the main problems of water-based acrylic emulsion system include unsatisfied entry into conduit, too fast drying, poor wiping property, poor color development (color rendering property) .
  • the main problems of water-based alkyd system include slow drying after wiping, or being even unable to completely dry, poor interlayer adhesion, poor paint film resistance. These problems make the existing water-based colorants poor performance, cumbersome application process, high cost, thus limiting the wide range of applications. Moreover, before the application process of colorants, a primer is usually required for close or semi-close treatment in order to obtain an improved vivid and uniform color effect.
  • a colorant composition which exhibits improved properties with respect to at least one of the above issues.
  • a colorant that has good overall performance in terms of wipeability, drying speed, color rendering, surface resistance, etc.
  • a colorant composition having a two-in-one use of a coloring agent and a primer is also highly desired.
  • a first aspect of the present application provides a composition
  • a composition comprising a component (A) , comprising at least one water-dilutable acrylic resin and water, and a component (B) comprising at least one colorant, wherein the at least one water-dilutable acrylic resin has at least one hydrophilic group and at least one self-crosslinking functional group, and the at least one water-dilutable acrylic resin in the component (A) has a (n) (average) particle size of from 0.01 ⁇ m to 0.1 ⁇ m.
  • a second aspect of the present application provides a coated article comprising a substrate and the composition as described herein or a cured coating formed therefrom at least partially applied on the substrate.
  • a water-dilutable acrylic resin is used as the main resin, which is present in component (A) in the form of smaller particle sizes. It has been found that the composition described herein can have good overall performance in two or more aspects of wipeability, drying speed, color development, surface resistance, intercoat adhesion, fillability, and resistance to grain raising/puffing. Moreover, the composition described herein can have a two-in-one use of a coloring agent (or a wipe stain) and a primer, which can save at least one sealing primer during application, thereby saving time and cost. The composition described herein can have both good comprehensive performance and two-in-one use.
  • Fig. 1 illustrates photographs of three exemplary embodiments in the sealing (or close) process for shallow conduit substrates, where (a) is a photograph of the exemplary embodiment with a sealing primer and a comparative sample, (b) is a photograph of the exemplary embodiment without a sealing primer and with a comparative sample, and (c) is a photograph of the exemplary embodiment without a sealing primer and with the composition as described herein.
  • Fig. 2 illustrates photographs of three exemplary embodiments in the open process for deep conduit substrates, where (a) is a photograph of the exemplary embodiment with a sealing primer and a comparative sample, (b) is a photograph of the exemplary embodiment without a sealing primer and with a comparative sample, and (c) is a photograph of the exemplary embodiment without a sealing primer and with the composition as described herein.
  • a coating composition that comprises “an” additive can be interpreted to mean that the coating composition includes “one or more” additives.
  • the singular form herein is intended to include the plural form unless otherwise indicated herein.
  • compositions comprising, including, containing, or having certain components, it is intended that the composition may include other optional components than the certain components expressly listed, and that the composition may consist of or be composed of the certain components; when a method is described as comprising, including, containing, or having certain steps, it is intended that the method may include other optional steps than the certain steps expressly listed, and that the method may consist of or be composed of the certain steps.
  • an element or component when it is described that an element or component is included in and/or selected from a list of recited elements or components, it is to be understood that the element or component can be any of the recited elements or components and can be selected from the group consisting of two or more of the recited elements or components.
  • a numerical range defined by an endpoint includes all any numerical value within that range.
  • a range of 1 to 5 encompasses numerical values of 1, 1.5, 2, 2.75, 3, 3.80, 4, 5, and the like.
  • the disclosed range of values includes all sub-ranges within that broader range.
  • a range of 1 to 5 includes sub-ranges of 1 to 4, 1.5 to 4.5, 1 to 2, and the like.
  • each point or single value can be used as lower or upper limit and combined with any other point or single value or combined with other lower or upper limits, and the resulting ranges should be understood as being explicitly disclosed in this application.
  • the term "or” as used herein is inclusive.
  • the phrase “A or B” means “A, B, or both A and B” , and can also be abbreviated as “A and/or B” . More specifically, any of the following conditions satisfy the condition “A or B” : A is true (or exists) and B is false (or does not exist) ; A is false (or does not exist) and B is true (or exists) ; or both A and B are true (or exist) .
  • exclusive “or” is represented herein by terms like “either A or B” and "one of A or B. "
  • the phrases “does not contain” and “is free of” mean that the composition does not contain the ingredient intentionally added.
  • the phrases “does not contain a certain component” and “is free of a certain component” can be understood to mean that the composition contains less than 1 wt. % (weight%) of the component, more preferably less than 0.5 wt. %, even more preferably less than 0.2 wt. %, most preferably less than 0.1 wt. %of the component, relative to total weight of the composition.
  • dispersion herein conforms to the definition in the IUPAC Compendium of Chemical Terminology (2007) , which defines a dispersion to be a material comprising more than one phase, where at least one of the phases consists of finely divided phase domains, often in the colloidal size range, distributed throughout a continuous phase domain.
  • dispersion refers to a mixture of a dispersible polymer and a dispersion medium (solvent or carrier fluid) . Unless otherwise stated, the term “dispersion” is intended to encompass the term “solution” .
  • aqueous dispersion refers to a dispersion in which the dispersion medium (solvent or carrier fluid) mainly or primarily contains water.
  • the dispersion medium comprises at least about 50 wt. %, preferably at least about 60 wt. %, more preferably at least 70 wt. %and at most about 99 wt. %and at most about 100 wt. %of water, based on the total weight of the dispersion medium.
  • aqueous dispersion is intended to include the terms “solution system” , "water-dilutable” system, or emulsion system with higher levels of water.
  • aqueous dispersion of resin refers to a stable dispersion of resin (i.e., polymer) in particulate form in an aqueous liquid medium, optionally with the aid of suitable dispersing aids such as surfactant and co-solvent.
  • suitable dispersing aids such as surfactant and co-solvent.
  • a stable dispersion do not separates into immiscible layers when stored at 49°C (120°F) or when a physical force such as vibration is applied for at least two weeks.
  • emulsion refers to an emulsified liquid formed by emulsification of a polymer in a liquid state or of a solution of a polymer dissolved in an organic solvent by an emulsifier in water, usually having a larger average particle size (e.g. from 0.2 to 1 ⁇ m) and opaque appearance.
  • water-dilutable resin means that the resin is capable of being diluted with water without the addition of an emulsifier for emulsification such that the resin is dispersed in water to form a stable aqueous dispersion, usually having a small average particle size (e.g. 0.1 ⁇ m, preferably from 0.015 to 0.05 ⁇ m, for example about 0.03 ⁇ m) and a transparent appearance.
  • a small average particle size e.g. 0.1 ⁇ m, preferably from 0.015 to 0.05 ⁇ m, for example about 0.03 ⁇ m
  • water-dilutable resins are quite different from resins that need to be emulsified to form an emulsion.
  • self-crosslinking when used in the context of a self-crosslinking polymer, refers to the capacity of a polymer to enter into a crosslinking reaction with itself and/or another molecule of the polymer, in the absence of an external crosslinker, to form a covalent linkage therebetween.
  • this crosslinking reaction occurs through reaction of complimentary reactive functional groups present on the self-crosslinking polymer itself or two separate molecules of the self-crosslinking polymer.
  • a coating applied on a surface or a substrate When used in the context of "a coating applied on a surface or a substrate” , the term “on” includes both coatings applied directly or indirectly to a surface or substrate. Thus, for example, a coating applied to a primer layer on a substrate is regarded as a coating applied on the substrate.
  • a composition comprising a component (A) , comprising at least one water-dilutable acrylic resin and water, and a component (B) comprising at least one colorant.
  • the at least one water-dilutable acrylic resin has at least one hydrophilic group and at least one self-crosslinking functional group, and the at least one water-dilutable acrylic resin in the component (A) has a particle size of from 0.01 ⁇ m to 0.1 ⁇ m.
  • the water-dilutable acrylic resin is obtained by reacting: (a) at least one ethylenically unsaturated monomer having self-crosslinkable functional group, at least one ethylenically unsaturated monomer having hydrophilic group, or combinations thereof.
  • at least one crosslinking agent may be added into reaction mixture.
  • the self-crosslinking (self-crosslinkable) functional group can be a ketone carbonyl (ketocarbonyl) group or an epoxy group, a hydrolyzable group, or an aziridinyl group.
  • the at least one ethylenically unsaturated monomer having at least one self-crosslinkable functional group comprises at least one ethylenically unsaturated monomer containing ketone carbonyl group or epoxy group, at least one ethylenically unsaturated monomer containing hydrolyzable group, at least one ethylenically unsaturated monomer containing aziridinyl group, or combinations thereof.
  • At least one ethylenically unsaturated monomer containing ketone carbonyl group or epoxy group comprises diacetone acrylamide, methyl vinyl ketone, acetoacetoxyethyl (meth) acrylate, glycidyl (meth) acrylate, (meth) allyl glycidyl ether, 1-allyloxy-3, 4-epoxybutane, 1- (3-butenyloxy) -2, 3-epoxypropane, 4-vinyl-1-cyclohexane-1, 2-epoxide, or combinations thereof.
  • the at least one ethylenically unsaturated monomer containing hydrolyzable group may be an alkoxysilyl group, such as a C1-4 alkoxysilyl group (such as a methoxysilyl group, ethoxysilyl group) .
  • the at least one ethylenically unsaturated monomer containing hydrolyzable group comprises vinyltrimethoxysilane, vinyltriethoxysilane, vinyltributoxysilane, vinylmethoxydimethylsilane, vinylethoxydimethylsilane, vinylisobutoxydimethylsilane, vinyldimethoxymethylsilane, vinyldiethoxymethylsilane, vinyltris (2-methoxyethoxy) silane, vinyldiphenylethoxysilane, vinyltriphenoxysilane, 3- (vinylphenylaminopropyl) trimethoxysilane, 3- (vinylbenzylaminopropyl) trimethoxysilane, 3- (vinylphenylaminopropyl) triethoxysilane, 3- (vinylbenzylaminopropyl) triethoxysilane, divinylbenzylaminopropyl) triethoxysilane, divinylbenzylaminoprop
  • the at least one ethylenically unsaturated monomer containing aziridinyl group comprises 2- (1-aziridinyl) ethyl (meth) acrylate, 2- (1-aziridinyl) propyl (meth) acrylate, 3- (1-aziridinyl) propyl (meth) acrylate, or combinations thereof.
  • the at least one ethylenically unsaturated monomer having hydrophilic group comprises at least one ethylenically unsaturated monomer containing hydroxyl group, at least one ethylenically unsaturated monomer containing carboxyl group, at least one ethylenically unsaturated monomer containing amido group, or combinations thereof.
  • Examples of the at least one ethylenically unsaturated monomer containing hydroxyl group may include, but not limited to, hydroxyalkyl esters of unsaturated fatty acids [such as mono-or di-hydroxy C2-6 alkyl esters of carboxylic acids, such as hydroxy C2-6 alkyl esters of (meth) acrylic acid, for example 2-hydroxyethyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate; and mono-or di-hydroxy C2-6 alkyl esters of maleic acid, such as 2-hydroxyethyl maleate, di (2-hydroxypropyl) maleate] ; and aliphatic, cycloaliphatic or aromatic vinyl compounds with hydroxyl group (such as alpha-hydroxystyrene) .
  • hydroxyalkyl esters of unsaturated fatty acids such as mono-or di-hydroxy C2-6 alkyl esters of carboxylic acids, such as hydroxy C
  • the at least one ethylenically unsaturated monomer containing hydroxyl group comprises hydroxyalkyl ester of (meth) acrylic acid, hydroxyalkyl ester of maleic acid, or combinations thereof.
  • the at least one ethylenically unsaturated monomer containing hydroxyl group may comprise hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate, hydroxybutyl (meth) acrylate, N-hydroxymethylacrylamide, 2-hydroxyethyl maleate, di (2-hydroxypropyl) maleate, or combinations thereof.
  • Examples of the at least one ethylenically unsaturated monomer containing carboxyl group may include, but not limited to, unsaturated carboxylic acids or anhydrides thereof, for example (meth) acrylic acid, crotonic acid, isocrotonic acid, ethylacrylic acid, propylacrylic acid, isopropylacrylic acid, itaconic acid, maleic anhydride and fumaric acid; and their salts, for example, alkali metal salts, alkaline earth metal salts, ammonium salts, amine salts; and half-esters of linear or branched alcohols having 1 to 20 carbon atoms with unsaturated polycarboxylic acids or their anhydrides, for example monomethyl maleate, monoethyl maleate, 2-ethylhexyl maleate.
  • unsaturated carboxylic acids or anhydrides thereof for example (meth) acrylic acid, crotonic acid, isocrotonic acid, ethylacrylic acid, propy
  • the at least one ethylenically unsaturated monomer containing carboxyl group comprises (meth) acrylic acid, crotonic acid, isocrotonic acid, ethylacrylic acid, propylacrylic acid, isopropylacrylic acid, itaconic acid, maleic anhydride, fumaric acid, or combinations thereof.
  • Examples of the at least one ethylenically unsaturated monomer containing amido group may include, but not limited to, C2-8 carboxylic acid amides that may be substituted by substituents, such as (meth) acrylamide, ⁇ -ethyl (meth) acrylamide, ⁇ -ethylmethyl (meth) acrylamide, N-methyl (meth) acrylamide, N-butoxymethyl (meth) acrylamide, diacetone (meth) acrylamide.
  • the substituent may be, for example, C1-4 alkyl, C1-4 alkoxy, C1-4 acyl and the like.
  • the ethylenically unsaturated monomer containing amido group comprises (meth) acrylamide, ⁇ -ethyl (meth) acrylamide, N-methyl (meth) acrylamide, N-butoxymethyl (meth) acrylamide, diacetone (meth) acrylamide, or combinations thereof.
  • (b) optional at least one crosslinking agent may be added in the reaction for preparation of the water-dilutable acrylic resin.
  • Any suitable crosslinking agent known in the art may be used.
  • the crosslinking agent may be a hydrazide.
  • Commonly used hydrazides are dihydrazide and polyhydrazide. Examples of dihydrazides include carbonic dihydrazide, oxalic dihydrazide, succinic dihydrazide, adipic dihydrazide, azelaic dihydrazide, sebacic dihydrazide.
  • adipic dihydrazide, azelaic dihydrazide, sebacic dihydrazide or their combinations may be used as crosslinking agent.
  • polyhydrazide examples include 3, 3, 3-nitrilotripropionhydrazide [N (CH 2 CH 2 CONHNH 2 ) 3 ] with N, N, N', N'-ethylenediaminetetrapropionhydrazide [ (H 2 NHNCOCH 2 CH 2 ) 2 NCH 2 CH 2 N (CH 2 CH 2 CONHNH 2 ) 2 ] , N-amino polyacrylamide containing about 10 mol %hydrazide with a degree of polymerization below 100, etc.
  • component (A) may also include a crosslinking agent.
  • a crosslinking agent Those skilled in the art would easily determine the appropriate amount of the crosslinking agent according to actual needs.
  • the amount of the crosslinking agent may be 0-0.8 wt.%, such as 0.1-0.5 wt. %, based on the total weight of component (A) .
  • the preferences of the crosslinking agent are the same as those described above.
  • the water-dilutable acrylic resin herein is synthesized by free radical solution polymerization in at least one organic solvent.
  • the water-dilutable acrylic resin in component (A) has a relatively small particle size of from 0.01 ⁇ m to 0.1 ⁇ m, such as from 0.01 to 0.07 ⁇ m, preferably from 0.015 to 0.05 ⁇ m, more preferably from 0.01 ⁇ m to 0.03 ⁇ m.
  • particle size herein refers to the average particle size, which can be measured by laser light scattering. For example, the measurement may be performed using a commercially available laser particle size analyzer. Usually, it can be considered that the measured average particle size is D50 or Dv50. The particular measurement method and measurement conditions can be easily determined by those skilled in the art.
  • the water-dilutable acrylic resin is used in the form of a resin solution.
  • the water-dilutable acrylic resin can have a solid content of 35-50%.
  • the water-dilutable acrylic resin may have a solid content of 38-45%, more preferably a solid content of 40-42%, such as a solid content of about 41%.
  • water-dilutable acrylic resin is usually purchased as resin solutions and used directly.
  • the at least one water-dilutable acrylic resin is present in amount of from 20 wt. %to 30 wt. %. Based on the weight of the component (A) , the at least one water-dilutable acrylic resin is present in amount of from 10 wt. %to 30 wt. %, preferably from 12 wt. %to 28 wt. %, for example about 25 wt. %. In some preferred embodiments, based on the weight of the component (A) , the at least one water-dilutable acrylic resin is present in amount of from about 20 wt. %to 30 wt. %.
  • the water-dilutable acrylic resin this disclosure is fundamentally different from the common water-based acrylic resin emulsion in the art.
  • the water-dilutable acrylic resin in this disclosure is prepared by hydrophilic modification of alcohol-soluble acrylic resin, and is soluble in water to form a homogeneous phase.
  • Water-dilutable acrylic resin not only retains some excellent properties of solvent-based resins (including, for example, good resistance, good clarity, excellent compatibility with many solvents and pigments, etc. ) , but also has significantly improved water solubility.
  • resins in ordinary water-based acrylic resin emulsions are usually obtained by polymerizing water-based monomers, are dispersed with large particle size in water, and exhibit in an emulsion state. So ordinary water-based acrylic resin emulsions cannot form a homogeneous phase, thereby limiting their permeability and transparency.
  • the water-dilutable acrylic resin herein has at least one self-crosslinking functional group in addition to the hydrophilic group.
  • the water-dilutable acrylic resins herein are capable of self-crosslinking, providing good crosslink density, good water resistance, and desired film-forming speed, and even providing blocking effects.
  • this unique combination of properties not only allows the preparation of stable aqueous systems with better environmental friendliness and workability, but also allows composition containing water-dilutable acrylic resin to be used for coloring at the same time meanwhile functioning as a sealing primer.
  • component (A) may also contain an acrylic emulsion.
  • the amount of acrylic emulsion is 0-15 wt. %, such as 5 wt. %, 8 wt. %, 10 wt. %, 12 wt. %.
  • component (A) contains no (is free of) or almost no acrylic emulsion, such as no more than 5 wt. %, no more than 3 wt. %, no more than 1 wt. %, or even no more than 0.2 wt. %of the weight of component (A) . It has now been found that component (A) containing no or almost no acrylic emulsion can further improve properties such as wipeability, entry into conduit, interlayer adhesion, water resistance, compared to component (A) containing acrylic emulsion.
  • composition or component (A) described herein may also contain suitable drying retarders.
  • the amount of drying retarder is 1-45 wt. %, such as 10-40 wt. %, 20-35 wt. %.
  • composition or component (A) described herein may also contain additional additives, such as but not limited to fillers, anti-skinning agents, driers, emulsifiers, anti-migration aids, antibacterial agents, chain extenders, lubricants, wetting agents, biocides, plasticizers, film forming auxiliaries, defoamers, colorants, waxes, antioxidants, corrosion inhibitors, antifreezes, rheology additives, thickening agents, dispersants, pH adjusters, adhesion promoters, UV stabilizers, leveling agents or combinations thereof.
  • Each optional ingredient is present in an amount sufficient for its intended purpose, but preferably such an amount does not adversely affect the coating composition or the cured coating resulting therefrom.
  • the component (A) comprises a film forming auxiliary, a drying retarder, a defoamer, a thickening agent, a wetting agent, or combinations thereof.
  • component (A) comprises from about 0 to about 30 wt. %, such as from about 0.1 to about 20 wt. %, of additional additives relative to the total weight of component (A) .
  • the amount of each additive in component (A) may each independently range from 0.1 wt. %to 10.0 wt. %, for example 0.2 wt. %, 0.3 wt. %, 0.4 wt. %, 0.6 wt. %, 0.7 wt. %, 0.8 wt. %, 0.9 wt.
  • component (A) may contain 1-5 wt. %of film forming auxiliaries, based on the weight of component (A) .
  • component (A) comprises 20-60 wt. %, for example 25 wt. %, 30 wt. %, 35 wt. %, 40 wt. %, 45 wt. %, 50 wt. %, relative to the total weight of component (A) .
  • component (A) may further comprise at least one co-solvent.
  • the amount of optional co-solvent, if present, is relatively low.
  • component (A) may contain 15 wt. %or less of the co-solvent, based on the total weight of component (A) .
  • the amount of co-solvent may be about 5-15 wt. %, preferably about 6-12 wt. %, more preferably about 8-10 wt. %, based on the total weight of component (A) .
  • the amount of co-solvent may be even more preferably about 6, 7, 8, 9, 10, 11 or 12 wt. %based on the total weight of component (A) .
  • the co-solvent can be an organic solvent commonly used in the art.
  • the co-solvent can be a mono-or polyhydric alcohol, such as propanol, butanol, hexanol; glycol ethers or esters, such as diethylene glycol dialkyl ethers having a C1-C6 alkyl group, dipropylene glycol dioxane having a C1-C6 alkyl group, ethoxypropanol, and butyl glycol; diols, such as ethylene glycol and propylene glycol; and ketones, such as methyl ethyl ketone, acetone, cyclohexanone; N-methylpyrrolidone, N-ethyl pyrrolidones; aromatic or aliphatic hydrocarbons such as toluene, xylene or linear or branched aliphatic C6-C12 hydrocarbons.
  • the co-solvent is water-miscible.
  • co-solvents include, but are not limited to, ethanol, isopropanol, butanol, butoxydiglycol, butyl glycol, dipropylene glycol methyl ether (DPM) , propylene glycol methyl ether, ethylene glycol butyl ether, dipropylene glycol butyl ether (DPnB) , ethylene glycol ethyl ether, ethylene glycol monomethyl ether, ethylene glycol monohexyl ether, ethylene glycol mono-n-butyl ether, diethylene glycol monomethyl ether, ethylene glycol mono-n-butyl ether base ether, tripropylene glycol monomethyl ether, ethylene glycol monoisobutyl ether, diethylene glycol monoisobutyl ether, propylene glycol monoisobutyl ether, ethylene glycol monophenyl ether, propylene glycol monophenyl
  • component (A) is in form of a solution, more preferably a substantially transparent solution.
  • Transparency of the liquid (component (A) or water-dilutable acrylic resin) can be determined by methods known in the art.
  • the transparency of the liquid can be measured according to the Chinese National Standard GB/T 1721-2008.
  • “Substantially transparent” means that the value of transparency measured by the method according to the Chinese National Standard GB/T 1721-2008 is at least 80, such as 82-100, at least 85 or at least 87.
  • component (B) comprises at least one colorant powder, at least one colorant paste, or combinations thereof.
  • Colorants may be used in powder, paste or other suitable form.
  • various colors of pigments, colorants, toners, dyes and metallic effect agents may be used. Pigments, colorants, toners, dyes and metallic effect agents will be collectively referred to herein as "colorants" , unless otherwise specified.
  • Pigments used in the colorant composition of the present disclosure are known in the art. Suitable pigments include titanium dioxide, carbon black, lamp black, black iron oxide, red iron oxide, clear red iron oxide, yellow iron oxide, clear iron yellow, brown iron oxide (blends of red and yellow oxides with black oxides) , phthalocyanine green, phthalocyanine blue, organic reds (such as naphthol red, quinacridone red, and toulidine red) , quinacridone magenta, quinacridone violet, DNA orange, organic yellow (such as monoazo yellow) or a combination thereof.
  • Suitable pigments include titanium dioxide, carbon black, lamp black, black iron oxide, red iron oxide, clear red iron oxide, yellow iron oxide, clear iron yellow, brown iron oxide (blends of red and yellow oxides with black oxides) , phthalocyanine green, phthalocyanine blue, organic reds (such as naphthol red, quinacridone red, and toulidine red) , quinacridone magenta, quinacridone
  • the weight of component (B) is 0-10%, preferably 3-8%, such as 4%, 5%, 6%or 7%, based on the total weight of component (A) and component (B) .
  • the composition described herein can include 0.1-30 wt. %of colorant, based on the total weight of the composition. In other embodiments, the composition described herein may comprise 1-6 wt. %of colorant, based on the total weight of the composition.
  • a coated article comprising: a substrate, and the composition described herein or a cured coating formed therefrom at least partially applied on the substrate.
  • the composition described herein or a cured coating formed therefrom can cover at least 50%, such as at least 80%, at least 90%, at least 95%, and even up to 99%or 100%of surface of the substrate.
  • Substrates are porous substrates such as paper, cardboard, wood veneer, particle board, fiberboard, composite board, solid wood and other wood substrates.
  • the substrate may be oak (eg, white oak and red oak) , pine (eg, white pine and southern ponderosa pine) , aspen, spruce, cherry, walnut, redwood, cedar, maple, mahogany, birch, hickory, walnut, ash, fraxinus mandshurica, rosewood, or derivatives thereof (such as veneer) .
  • Various porous substrates may be colored by using the composition described in the present disclosure. This type of wood is often used to prepare furniture such as kitchen cabinets, bathrooms, dining tables, school desks, dressers and other furniture.
  • composition of the present application can be applied by conventional methods known to those of ordinary skill in the art.
  • the composition is applied by brushing, spraying and other application methods known in the art.
  • a coating may be formed from the composition of the present application, and thus also falls within the protection scope of the present application.
  • the present application also provides a coating obtainable from the composition described herein.
  • Transparency of liquid is measured according to Chinese National Standard GB/T 1721-2008.
  • Wipeability Parallel comparison test is carried out, under the same environmental conditions (room temperature and 60%humidity) and the same wiping method, wherein smooth wiping is scored 5 points, sluggish wiping is scored 1 point, and the wipeability is scored in 5 grades.
  • Performance of entering conduit is observed and evaluated under the same conditions (room temperature and 60%humidity) , the same application way and drying way, wherein 1 represents the worst performance, 5 represents the best.
  • Drying speed The sample to be tested is applied with a thickness of 80 ⁇ m, and dried for a given time at a temperature of 25°C (room temperature) and a humidity of 60%, and then the degree of hard dryness of the resulting coating is determined. The test results are recorded on a scale of from 1 to 5, with 1 being the worst (not completely dry) and 5 the best (completely drying) .
  • Water resistance is measured according to the Chinese National Standard GB/T3324-2017, with 1 being the worst and 5 the best, and then is scored in 5 grades.
  • Alcohol resistance is measured according to the Chinese National Standard GB/T3324-2017, with 1 being the worst and 5 the best, and then is scored in 5 grades.
  • Fillability is scored in 5 grades, wherein 5 represents full filling of wood grain with good contrast, and 0 represents insufficient or uneven filling of wood grain with poor contrast.
  • Color effect Surface of the sample to be tested is visually observes and scored in 5 grades in aspects of color vividness, uniformity and texture clarity. An appearance with bright and uniform color and clear texture is the best and scored 5, whereas 1 represents the worst.
  • Interlayer adhesion is measured according to the Chinese National Standard GB/T3324-2017.10 groups of crossed grids with about 2 mm spacing were scribed out with a scoring knife, and a transparent tape is applied to the scored surface and then torn off. The adhesion are scored with a scale from 0 to 5 in aspects of color shedding in grids, with 0 being the best and 5 being the worst.
  • the appearance of component (A) is in the form of a substantially transparent solution (not in the form of an emulsion) , and the transparency was measured as 87.
  • Component (B) was formulated, which was a water-based glaze paste.
  • Component A and Component B were mixed in a weight ratio of 100: 5, to obtain a colorant composition.
  • Comparative Sample 1 Commercially available acrylic emulsion systems and waterborne alkyd resin systems were used as Comparative Sample 1 and Comparative Sample 2, respectively, as component (A) .
  • component (B) Using the same component (B) and amounts of components as in Example 1, two comparative colorant compositions were obtained, respectively.
  • the application was carried out using the construction process and conditions shown in Table 2, wherein in the wiping process, the two comparative colorant compositions prepared in Comparative Example 1 were used.
  • Example 1 As a coloring agent (or a wipe stain) and a sealing primer, the colorant composition of Example 1 comprising Sample 1 was used and applied according to the process and conditions shown in Table 4.
  • the water-based coloring agent comprising Comparative Sample 1 was used as a control.
  • Fraxinus mandshurica veneer or cherry wood veneer was used as the substrate to study the effect of the composition in sealing (or close) process of the shallow conduit substrate and in the process of the deep conduit substrate, respectively.
  • the application was carried out at room temperature (RT) and 60%humidity.
  • Solution Three using the composition described herein exhibited the same or similar effect in the resistance to grain raising. This is very surprising. Because in common application processes, a sealing primer is usually required to prevent the grain raising of wood substrates, and by using the composition described herein, better resistance to grain raising can be obtained without applying a sealing primer. It can be seen that the composition described herein has excellent sealing performance, which allows to omit at least one sealing primer in the sealing process or open process, thereby saving time and cost greatly, meanwhile exhibiting excellent color effect and adhesion.
  • Embodiment 1 A composition comprising: a component (A) , comprising at least one water-dilutable acrylic resin and water, and a component (B) comprising at least one colorant, wherein the at least one water-dilutable acrylic resin has at least one hydrophilic group and at least one self-crosslinking functional group, and the at least one water-dilutable acrylic resin in the component (A) has a particle size of from 0.01 ⁇ m to 0.1 ⁇ m.
  • Embodiment 2 An embodiment of Embodiment 1, wherein the water-dilutable acrylic resin is obtained by reacting: (a) at least one ethylenically unsaturated monomer having self-crosslinkable functional group, at least one ethylenically unsaturated monomer having hydrophilic group, or combinations thereof; and (b) optionally at least one crosslinking agent.
  • Embodiment 3 An embodiment of Embodiment 2, wherein the at least one ethylenically unsaturated monomer having at least one self-crosslinkable functional group comprises at least one ethylenically unsaturated monomer containing ketone carbonyl group or epoxy group, at least one ethylenically unsaturated monomer containing hydrolyzable group, at least one ethylenically unsaturated monomer containing aziridinyl group, or combinations thereof.
  • Embodiment 4 An embodiment of Embodiment 3, wherein the at least one ethylenically unsaturated monomer containing ketone carbonyl group or epoxy group comprises diacetone acrylamide, methyl vinyl ketone, acetoacetoxyethyl (meth) acrylate, glycidyl (meth) acrylate, (meth) allyl glycidyl ether, 1-allyloxy-3, 4-epoxybutane, 1- (3-butenyloxy) -2, 3-epoxypropane, 4-vinyl-1-cyclohexane-1, 2-epoxide, or combinations thereof.
  • the at least one ethylenically unsaturated monomer containing ketone carbonyl group or epoxy group comprises diacetone acrylamide, methyl vinyl ketone, acetoacetoxyethyl (meth) acrylate, glycidyl (meth) acrylate, (meth) allyl glycidyl
  • Embodiment 5 An embodiment of Embodiment 3, wherein the at least one ethylenically unsaturated monomer containing hydrolyzable group comprises vinyltrimethoxysilane, vinyltriethoxysilane, vinyltributoxysilane, vinylmethoxydimethylsilane, vinylethoxydimethylsilane, vinylisobutoxydimethylsilane, vinyldimethoxymethylsilane, vinyldiethoxymethylsilane, vinyltris (2-methoxyethoxy) silane, vinyldiphenylethoxysilane, vinyltriphenoxysilane, 3- (vinylphenylaminopropyl) trimethoxysilane, 3-(vinylbenzylaminopropyl) trimethoxysilane, 3- (vinylphenylaminopropyl) triethoxysilane, 3-(vinylbenzylaminopropyl) triethoxysilane, divinyldimethoxysilane, divinyl
  • Embodiment 6 An embodiment of Embodiment 3, wherein the at least one ethylenically unsaturated monomer containing aziridinyl group comprises 2- (1-aziridinyl) ethyl (meth) acrylate, 2- (1-aziridinyl) propyl (meth) acrylate, 3- (1-aziridinyl) propyl (meth) acrylate, or combinations thereof.
  • Embodiment 7 An embodiment of Embodiment 2, wherein the at least one ethylenically unsaturated monomer having hydrophilic group comprises at least one ethylenically unsaturated monomer containing hydroxyl group, at least one ethylenically unsaturated monomer containing carboxyl group, at least one ethylenically unsaturated monomer containing amido group, or combinations thereof.
  • Embodiment 8 An embodiment of Embodiment 7, wherein the at least one ethylenically unsaturated monomer containing hydroxyl group comprises hydroxyalkyl ester of (meth) acrylic acid, hydroxyalkyl ester of maleic acid, or combinations thereof; preferably hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate, hydroxybutyl (meth) acrylate, N-hydroxymethylacrylamide, 2-hydroxyethyl maleate, di (2-hydroxypropyl) maleate, or combinations thereof.
  • Embodiment 9 An embodiment of Embodiment 7, wherein the at least one ethylenically unsaturated monomer containing carboxyl group comprises (meth) acrylic acid, crotonic acid, isocrotonic acid, ethylacrylic acid, propylacrylic acid, isopropylacrylic acid, itaconic acid, maleic anhydride, fumaric acid, or combinations thereof.
  • Embodiment 10 An embodiment of Embodiment 7, wherein the ethylenically unsaturated monomer containing amido group comprises (meth) acrylamide, ⁇ -ethyl (meth) acrylamide, N-methyl (meth) acrylamide, N-butoxymethyl (meth) acrylamide, diacetone (meth) acrylamide, or combinations thereof.
  • Embodiment 11 An embodiment of any one of the preceding Embodiments, wherein the water-dilutable acrylic resin in the component (A) has a particle size of from 0.01 to 0.05 ⁇ m, preferably from 0.01 to 0.03 ⁇ m.
  • Embodiment 12 An embodiment of any one of the preceding Embodiments, wherein the component (A) is in form of a substantially transparent solution.
  • Embodiment 13 An embodiment of any one of the preceding Embodiments, wherein based on the weight of the component (A) , the at least one water-dilutable acrylic resin is present in amount of from 10 wt. %to 30 wt. %, preferably from 12 wt. %to 28 wt. %.
  • Embodiment 14 An embodiment of any one of the preceding Embodiments, wherein the component (A) further comprises a film forming auxiliary, a drying retarder, a defoamer, a thickening agent, a wetting agent, or combinations thereof.
  • Embodiment 15 An embodiment of any one of the preceding Embodiments, wherein the component (B) comprises at least one colorant powder, at least one colorant paste, or combinations thereof.
  • Embodiment 16 A coated article, comprising: a wood substrate, and the composition according to any one of Embodiments 1 to 15 or a cured coating formed therefrom at least partially applied on the wood substrate.
  • Embodiment 17 An embodiment of Embodiment 16, wherein the composition or the cured coating is in direct contact with the wood substrate.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Nanotechnology (AREA)
  • Paints Or Removers (AREA)

Abstract

La présente invention concerne une composition colorante et un article revêtu. La composition colorante comprend un composant (A) comprenant au moins une résine acrylique diluable dans l'eau et de l'eau, et un composant (B) comprenant au moins un colorant, l'au moins une résine acrylique diluable dans l'eau ayant au moins un groupe hydrophile et au moins un groupe fonctionnel auto-réticulable, et l'au moins une résine résine acrylique diluable dans l'eau dans le composant (A) a une taille de particules de 0,01 µm à 0,1 µm. La composition selon l'invention présente des avantages comprenant une propriété d'essuyage, une vitesse de séchage rapide, une propriété de rendu de couleur et une résistance de surface excellentes, et peut être utilisée en tant que combinaison d'un agent colorant (ou d'une tâche d'essuyage) et d'un apprêt, de manière à omettre au moins un apprêt d'étanchéité, à économiser du temps et de l'argent dans un procédé ouvert.
PCT/CN2022/127604 2021-10-29 2022-10-26 Composition colorante et article revêtu WO2023072128A1 (fr)

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JP2000043409A (ja) * 1998-07-29 2000-02-15 Daicel Chem Ind Ltd 被記録媒体及びその製造法
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