WO2022100867A1 - Polymère en tant qu'agent dispersant universel pour pigments dans une composition de colorant ou de revêtement - Google Patents

Polymère en tant qu'agent dispersant universel pour pigments dans une composition de colorant ou de revêtement Download PDF

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Publication number
WO2022100867A1
WO2022100867A1 PCT/EP2020/082241 EP2020082241W WO2022100867A1 WO 2022100867 A1 WO2022100867 A1 WO 2022100867A1 EP 2020082241 W EP2020082241 W EP 2020082241W WO 2022100867 A1 WO2022100867 A1 WO 2022100867A1
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WO
WIPO (PCT)
Prior art keywords
bis
hydroxyphenyl
polymer
pigment
pigments
Prior art date
Application number
PCT/EP2020/082241
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English (en)
Inventor
Ryan LIN WEI'AN
Lichang Zhou
Peng Xu
Wee Shong Chin
Original Assignee
Rhodia Operations
National University Of Singapore
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Rhodia Operations, National University Of Singapore filed Critical Rhodia Operations
Priority to PCT/EP2020/082241 priority Critical patent/WO2022100867A1/fr
Publication of WO2022100867A1 publication Critical patent/WO2022100867A1/fr

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Classifications

    • 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
    • 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

Definitions

  • the present invention relates to a polymer which could be used as universal dispersant for pigments in colorant or coating composition.
  • the present invention further provides a colorant composition comprising the same, which has low active on pigment dosage.
  • the present invention further provides a coating composition comprising the polymer as universal dispersant for pigments which has favorable tinting strength and dispersion performance.
  • Pigments are ordinarily organic or inorganic dry powders that incorporate a mixture of primary particles, aggregates and agglomerates.
  • the pigment should be dispersed homogeneously throughout the coating composition in order to ensure a uniform appearance of the final coating.
  • the process of pigment dispersion can be divided into three different stages, namely wetting, grinding and stabilization stage.
  • pigments are usually wetted, disaggregated and de-agglomerated in a vehicle to obtain a dispersion of the pigment particles. Wetting involves incorporation of the pigment into the vehicle replacing pigment-air interfaces with pigmentvehicle interfaces.
  • Dispersants can also facilitate the dispersion of pigments by reducing the interfacial tension between pigment-vehicle interface.
  • pigment agglomerates are broken down to its primary particle size by mechanical shear force.
  • pigment dispersant will absorb onto the surface of the pigment particle and prevent flocculation by electrostatic and/or steric repulsion force.
  • An ideal pigment dispersion consists of a homogenous suspension of pigment particles with good colloidal stability over time.
  • Pigments impart color to both solvent and latex paints and coatings. They also contribute to the opacity, durability and hardness of paint coatings. They are added to paint in the form of dry pigment powders and/or pigmented tinting concentrate during paint manufacture at the paint plant. In addition, especially for consumer latex paints, they may be added in the form of pigmented paint tinting concentrates at the point of sale, such as at retail paint stores. Essentially, the consumer may choose a custom-made color of the paint by having the retailer add a tinting concentrate to a white or tintable base.
  • Tinting strength refer to the ability of a color pigment to change the hue of a paint. It is highly dependent on the particle size and dispensability of the color pigment in a paint system. A finely disperse state of color pigment in paint is necessary to achieve high color tinting strength. Low tinting strength will require higher dosage of colorant to achieve a desired color shades. As such, formulation cost will increase and it can leads to complication during application and performance issue.
  • color paints can be instantly produced at the point of sale by mixing precise amount of concentrated colorant into a white base paint.
  • Such paint tinting system is robust and makes possible for paint store to provide thousands of colors with limited inventory.
  • this process involves mixing of multiple colorants containing surfactants and pigments of different size and chemistry into different paint base.
  • surfactant combinations are generally less than optimal and it can lead to loss of pigment stabilization, flocculation and poor color acceptance. Over-dosage of dispersants and other are necessary to resolve such issue but it can leads to problem such as surfactant leeching, foaming, poor water resistance and rheology control.
  • the present invention provide a polymer which solves the above technical needs, meaning the polymer can disperse a wide range of pigment chemistries with low active dosage.
  • the polymer provided by the present invention has a formula of wherein
  • Ar is derived from resorcinol, hydroquinone, 2,2-bis(4- hydroxyphenyl)propane (bisphenol A), poly(Bisphenol A-co-epichlorohydrin), isomer mixtures of dihydroxydiphenylmethane (bisphenol F), 4,4'- dihydroxydiphenylcyclohexane, 2,2-bis(4-hydroxy-3-methylphenyl)propane, 4,4'- dihydroxybiphenyl, 4,4'-dihydroxybenzophenone, 1,1-bis(4- hydroxyphenyl)ethane, 2,2-bis-4-(2'-hydroxypropoxy)phenylpropane, 1 , 1 -bis(4- hydroxyphenyl)isobutane, 2,2-bis(4-hydroxy-3-tert-butylphenyl)propane, bis(2- hydroxynaphthyl)methane, 1,5-dihydroxynaphthalene, tris(4- hydroxyphenyl)
  • RT is a Ci to Cis alkyl
  • R 2 and R 3 are each independently selected from •Y o L T o OH wherein L is a Ci to C 6 saturated or unsaturated alkylene group or C 3 to C 8 cycloalkylene group; n is an integer of 3 to 20 , p is an integer of 0 to 30, q is an integer of 5 to
  • a colorant composition comprising the polymer as illustrated above and a pigment selected from organic or inorganic pigments or the combination thereof.
  • a coating composition comprising I) a binding polymer which is selected from pure acrylic, styrene acrylic, fluoropolymer acrylic, urethane acrylic, vinyl acrylic and/or an acrylated ethylene vinyl acetate copolymer or combinations thereof;
  • any particular upper concentration, weight ratio or amount can be associated with any particular lower concentration, weight ratio or amount, respectively.
  • alkyl means a saturated hydrocarbon radical, which may be straight, branched or cyclic, such as, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, t-butyl, pentyl, n-hexyl, cyclohexyl.
  • (Cn-Cm) in reference to an organic group, wherein n and m are each integers, indicates that the group may contain from n carbon atoms to m carbon atoms per group.
  • Pigment usually in the form of organic or inorganic dry powder, is a substance that imparts color to another substance or mixture.
  • “Colorant” is also a substance that imparts color to another substance or mixture, and generally includes pigment and other additives.
  • the polymer as universal dispersant for dispersing pigments
  • the polymer as universal dispersant for dispersing pigments in colorant or coating has a formula of wherein
  • Ar is derived from resorcinol, hydroguinone, 2,2-bis(4- hydroxyphenyl)propane (bisphenol A), poly(Bisphenol A-co-epichlorohydrin), isomer mixtures of dihydroxydiphenylmethane (bisphenol F), 4,4'- dihydroxydiphenylcyclohexane, 2,2-bis(4-hydroxy-3-methylphenyl)propane, 4,4'- dihydroxybiphenyl, 4,4'-dihydroxybenzophenone, 1,1-bis(4- hydroxyphenyl)ethane, 2,2-bis-4-(2'-hydroxypropoxy)phenylpropane, 1 , 1 -bis(4- hydroxyphenyl)isobutane, 2,2-bis(4-hydroxy-3-tert-butylphenyl)propane, bis(2- hydroxynaphthyl)methane, 1,5-dihydroxynaphthalene, tris(4- hydroxyphenyl)me
  • RT is a Ci to Cis alkyl
  • R 2 and R 3 are each independently selected from T o o wherein L is a Ci to C 6 saturated or unsaturated alkylene group or C 3 to C 8 cycloalkylene group; n is an integer of 3 to 20 , p is an integer of 0 to 30, g is an integer of 5 to 60.
  • Ar is derived from 2,2-bis(4- hydroxyphenyl)propane (bisphenol A), or isomer mixtures of dihydroxydiphenylmethane (bisphenol F).
  • L is a saturated Ci to C 6 alkylene group, or C 3 to C 8 cycloalkylene group; preferably L is a linear saturated Ci to C 6 alkylene, more preferably L is selected from methylene, ethylene, propylene or butylene, cyclopropylene, cyclobutylene, cyclopentylene, or cylcohexylene.
  • the polymer as provided is prepared from the composition comprising: a) glycidyl ether of polyhydric phenol; b) alkoxylated primary amine; and c) optionally C 3 to C 8 aliphatic dicarboxylic acid, C 5 to C cycloaliphatic dicarboxylic acid or the derivatives thereof.
  • the polyhydric phenol is the one or more selected from the group consisting of resorcinol, hydroquinone, 2,2-bis(4- hydroxyphenyl)propane (bisphenol A), poly(Bisphenol A-co-epichlorohydrin), isomer mixtures of dihydroxydiphenylmethane (bisphenol F), 4,4'- dihydroxydiphenylcyclohexane, 2,2-bis(4-hydroxy-3-methylphenyl)propane, 4,4'- dihydroxybiphenyl, 4,4'-dihydroxybenzophenone, 1 ,1-bis(4- hydroxyphenyl)ethane, 2,2-bis-4-(2'-hydroxypropoxy)phenylpropane, 1 , 1 -bis(4- hydroxyphenyl)isobutane, 2,2-bis(4-hydroxy-3-tert-butylphenyl)propane, bis(2- hydroxynaphthyl)
  • the alkoxylated primary amine is selected from an ethoxylated and/or propoxylated aliphatic primary amine having 1 to 18 carbon atoms
  • the exemplary aliphatic primary amine include but not limited to methyl amine, ethyl amine, propyl amine, or butyl amine.
  • C 3 to C 8 aliphatic dicarboxylic acid is selected from malonic acid, succinic acid and maleic acid or the combination thereof.
  • the derivatives of the C 3 to C 8 aliphatic dicarboxylic acid or C 5 to C cycloaliphatic dicarboxylic acid can be contemplated in the present invention.
  • the derivatives of the C 3 to C aliphatic or C 5 to C cycloaliphatic dicarboxylic acid mean acid esters, acid halides, acid anhydrides, or lactone thereof.
  • the polymer of the present invention as universal dispersant for dispersing pigments has a weight molecular weight ranging from 3,000 to 20,000g/mol determined by GPC measurement.
  • the polymer of the present invention as universal dispersant for dispersing pigments has an acid value ranging from 10 to 50 mg KOH/g determined by titration.
  • a colorant composition comprising a) the polymer as universal dispersant for dispersing pigments as illustrated above; and b) a pigment selected from organic or inorganic pigments or the combination thereof.
  • the colorant composition is provided as liquid or paste or any other formulation according to the actual need.
  • the dosage of the polymer as illustrated above may vary for different pigments and can be easily determined by technical experts in the art, for example the dosage can be 0.8 to 2.0 wt.% in case of yellow pigments, and 25 to 40 wt.% for black pigments.
  • the pigment contemplated in the present invention is selected from organic or inorganic pigments or the combination thereof.
  • Suitable inorganic pigments include but not limited to titanium dioxide pigments, such as Pigment White 6, and bismuth vanadate pigments; lead chromate pigments, such as C.l. Pigment Yellow 34 or 104 or C.l. Pigment Orange 21 ; molybdate red or molybdate orange pigments, such as C.l. Pigment Red 104; cerium sulfide pigments, such as C.l. Pigment Orange 75 or C.l. Pigment Red 265; complex inorganic chromatic pigments, such as C.l. Pigment Yellow 53, 118, 119, 157, 158, 159, 160, 161 , 162, 163, 164 or 189; C.l.
  • Pigment Brown 24, 33, 34, 35, 37, 39 or 40 C.l. Pigment Green 50 or C.l. Pigment Blue 28, 36 or 72; and silicate pigments, such as C.l. Pigment Blue 29, C.l. Pigment Violet 15 or C.l. Pigment Red 259.
  • Suitable organic pigments include but not limited to copper phthalocyanine pigments, such as C.l. Pigment Blue 15, 15:1 , 15:2, 15:3, 15:4, 15:6, 16 or C.l. Pigment Green 7, 36; Diketopyrrolo-pyrrole pigments, such as C.l. Pigment Red 254, 255, 264, 270, 272 or C.l. Pigment Orange 71 ,73; Dioxazine pigments, such as C.l. Pigment Violet 23, 37; Carbon pigment, such as C.l. Carbone black 6, 7, 8; Arylamide pigments, such as C.l.
  • Pigment Yellow 1 3, 65, 73, 74, 75, 97, 111 ; and Benzimidazolone pigments, such as C.l. Pigment Red 171 , 175, 176, 185, 208 or C.l. Pigment Violet 32 or C.l. Pigment Brown 25.
  • Benzimidazolone pigments such as C.l. Pigment Red 171 , 175, 176, 185, 208 or C.l. Pigment Violet 32 or C.l. Pigment Brown 25.
  • the colorant composition of the present invention can further comprises additives such as defoamer, rheology modifier, filler, neutralizing agent, biocide and the like.
  • the colorant composition comprises aqueous carrier such as water and organic solvents which are miscible with water.
  • the coating composition is a mixture of the coating composition.
  • a coating composition comprising:
  • a binding polymer which is selected from pure acrylic, styrene acrylic, fluoropolymer acrylic, urethane acrylic, vinyl acrylic and/or an acrylated ethylene vinyl acetate copolymer or combinations thereof;
  • coating refers to the paint composition after it has been applied to a substrate and has dried.
  • coating and “paint” can be used interchangeably.
  • a substrate herein is a surface, such as a composite building material. Paint compositions, formulations and coatings therefrom as described herein will be suitable for any building product, whether natural, synthetic or composite in nature.
  • a coating composition formulation described has a binding polymer or mixture thereof.
  • the binding polymer may be derived from at least one acrylic monomer, such as an acrylic acid, acrylic acid ester, methacrylic acid, and methacrylic acid ester.
  • the binding polymer is derived from one or more monomers, examples of which include polyvinylidine fluoride, styrene, alpha-methyl styrene, vinyl chloride, acrylonitrile, methacrylonitrile, ureido methacrylate, vinyl acetate, vinyl esters of branched tertiary monocarboxylic acids, itaconic acid, crotonic acid, maleic acid, fumaric acid, ethylene, and C 4 -C 8 conjugated dienes.
  • monomers examples of which include polyvinylidine fluoride, styrene, alpha-methyl styrene, vinyl chloride, acrylonitrile, methacrylonitrile, ureido methacrylate, vinyl acetate, vinyl esters of branched tertiary monocarboxylic acids, itaconic acid, crotonic acid, maleic acid, fumaric acid, ethylene, and C 4 -C 8 conjugated dienes.
  • the binding polymer is selected from the acrylic latex polymers including methyl methacrylate, butyl- or isobutylmethacrylate and their blends, and polymerize with longer chain substituents.
  • the component II of the polymer as universal dispersant and the component III of the pigments are illustrated as above, they can be provided as a whole as a colorant composition, or provided separately.
  • the universal dispersant has a dosage of 0.1 to 4 wt.% for inorganic pigment and 3 to 60 wt.% for organic pigment, based on the total amount of the water borne coating composition.
  • the coating composition is waterborne or solvent based. In one preferred embodiment of the present invention, the coating composition is a waterborne composition.
  • the water-borne coating composition is prepared by a well-known dispersion process wherein water as the dispersion medium. Thickener were added for rheological control. In most cases the thickener is a cellulosic compound that swells in water. Neutralizer, wetting and dispersing agent, defoamer and several other additives are further mixed into the system. Pigments and fillers were added under high sheer speed and grind to disperse form commonly referred to as mill-base. Later, in the typical dispersion process, the mill-base is let down (diluted) with water, binding polymer and additional additives such as coalescing agent, rheology modifiers etc.
  • the synthesis of the polymer involves step-growth polymerization via epoxy ring opening of a glycidyl ether of polyhydric phenols by an alkoxylated primary amine.
  • the glycidyl ether of polyhydric phenols the alkoxylated amine (equal amount) were mixed in ethanol and refluxed at 85°C for 24 hours under N2 blanketing.
  • the resulting product was then dried via rotary evaporator at 60°C.
  • the obtained product was further functionalized with excess lactone via esterification reaction.
  • the lactone (2 eq) was added to the obtained product in tetra hydrofuran and refluxed for 24 hours at 85°C under N2 blanketing. Unreacted lactone were removed by dialysis using a dialysis bag in ethanol for 2 hours at 40°C followed by drying via rotary evaporation at 60°C, thereby to provide the polymer.
  • AOP refers to the optimum dispersant dosage to obtain the minimum viscosity point.
  • the AOP is determined as follows: Deionized water, defoamer, neutralizer and zirconium beads was first added into a grinding container. Mixture was then agitated using a dispermill follow by the addition of pigment powder. Mixture then undergo high shear grinding for 15mins to form a thick pigment slurry. Low shear viscosity was then measured with a Brookfield viscometer. A small amount of dispersant was then added and grind for 3mins before viscosity measurement. This process was repeated until viscosity minimum is achieve. AOP is the amount of the added dispersant by which the minimum viscosity is obtained.
  • the tinting strength of the dried film was determined by using a Color Spectrophotometer (BYK-Gardner).
  • the polymer provided in the present invention has lower effective dosage (AOP) in colorant, and it further proves in table 4 that the polymer of the present invention can disperse various pigments, both inorganic and organic, with lower effective dosage and favorable tinting strength and dispersion performance, compared to the Benchmark BYK 190.

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

Abstract

La présente invention concerne un polymère qui pourrait être utilisé en tant qu'agent dispersant universel pour des pigments dans une composition de colorant ou de revêtement. La présente invention concerne également une composition de colorant le comprenant, qui présente un faible dosage à effet actif sur les pigments. La présente invention concerne en outre une composition de revêtement comprenant le polymère en tant qu'agent dispersant universel pour des pigments qui présente un pouvoir de coloration et une performance de dispersion favorables.
PCT/EP2020/082241 2020-11-16 2020-11-16 Polymère en tant qu'agent dispersant universel pour pigments dans une composition de colorant ou de revêtement WO2022100867A1 (fr)

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PCT/EP2020/082241 WO2022100867A1 (fr) 2020-11-16 2020-11-16 Polymère en tant qu'agent dispersant universel pour pigments dans une composition de colorant ou de revêtement

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PCT/EP2020/082241 WO2022100867A1 (fr) 2020-11-16 2020-11-16 Polymère en tant qu'agent dispersant universel pour pigments dans une composition de colorant ou de revêtement

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WO2022100867A1 true WO2022100867A1 (fr) 2022-05-19

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1111015A1 (fr) * 1999-12-20 2001-06-27 Eastman Kodak Company Procédé de production d'une encre pour l'impression par jet d'encre
CN101597446A (zh) * 2008-12-25 2009-12-09 天津兆阳纳米科技有限公司 一种稳定型黄色纳米水性颜料分散液
US20140007794A1 (en) * 2012-07-03 2014-01-09 Columbia Insurance Company Universal VOC-Free Metallic/Pearlescent Colorants
WO2017029290A1 (fr) * 2015-08-20 2017-02-23 Basf Se Préparations universelles de pigments destinées à être utilisées sur le lieu de vente
CN107083129A (zh) * 2016-05-20 2017-08-22 南京长江涂料有限公司 一种水性超薄型钢结构防火涂料及其制备方法
CN107840848A (zh) * 2016-09-18 2018-03-27 南京工业大学 一类吡咯并吡咯二酮聚醚衍生物及其制备方法

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1111015A1 (fr) * 1999-12-20 2001-06-27 Eastman Kodak Company Procédé de production d'une encre pour l'impression par jet d'encre
CN101597446A (zh) * 2008-12-25 2009-12-09 天津兆阳纳米科技有限公司 一种稳定型黄色纳米水性颜料分散液
US20140007794A1 (en) * 2012-07-03 2014-01-09 Columbia Insurance Company Universal VOC-Free Metallic/Pearlescent Colorants
WO2017029290A1 (fr) * 2015-08-20 2017-02-23 Basf Se Préparations universelles de pigments destinées à être utilisées sur le lieu de vente
CN107083129A (zh) * 2016-05-20 2017-08-22 南京长江涂料有限公司 一种水性超薄型钢结构防火涂料及其制备方法
CN107840848A (zh) * 2016-09-18 2018-03-27 南京工业大学 一类吡咯并吡咯二酮聚醚衍生物及其制备方法

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