US20190031880A1 - Modified pigments and use thereof - Google Patents

Modified pigments and use thereof Download PDF

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Publication number
US20190031880A1
US20190031880A1 US16/044,960 US201816044960A US2019031880A1 US 20190031880 A1 US20190031880 A1 US 20190031880A1 US 201816044960 A US201816044960 A US 201816044960A US 2019031880 A1 US2019031880 A1 US 2019031880A1
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Prior art keywords
pigment
interface
modified
organic pigment
modified organic
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Inventor
Pedro Cavaleiro
Matthias Bouwman
Pascal Senter
Philippe Favresse
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Evonik Operations GmbH
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Evonik Degussa GmbH
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Assigned to EVONIK DEGUSSA GMBH reassignment EVONIK DEGUSSA GMBH ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: SENTER, Pascal, CAVALEIRO, PEDRO, FAVRESSE, PHILIPPE, BOUWMAN, Matthias
Publication of US20190031880A1 publication Critical patent/US20190031880A1/en
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Priority to US17/158,498 priority Critical patent/US20210163751A1/en
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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
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0001—Post-treatment of organic pigments or dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/0084—Dispersions of dyes
    • C09B67/0085—Non common dispersing agents
    • C09B67/0089—Non common dispersing agents non ionic dispersing agent, e.g. EO or PO addition products
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0001—Post-treatment of organic pigments or dyes
    • C09B67/002—Influencing the physical properties by treatment with an amine
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0001—Post-treatment of organic pigments or dyes
    • C09B67/0003—Drying, e.g. sprax drying; Sublimation of the solvent
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0001—Post-treatment of organic pigments or dyes
    • C09B67/0017—Influencing the physical properties by treatment with an acid, H2SO4
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/0084—Dispersions of dyes
    • C09B67/0085—Non common dispersing agents
    • C09B67/009—Non common dispersing agents polymeric dispersing agent
    • 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
    • C09D11/00—Inks
    • C09D11/02—Printing inks
    • C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
    • C09D11/037—Printing inks characterised by features other than the chemical nature of the binder characterised by the pigment
    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes
    • 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
    • C09D7/60—Additives non-macromolecular
    • C09D7/63—Additives non-macromolecular organic

Definitions

  • the present invention relates to modified organic pigments, and to the production and use thereof in paints, varnishes, printing inks and other coating materials.
  • Pigments are colouring substances present in insoluble dispersed form in the application medium.
  • Application media are, for example, organic solvents, paints, varnishes, pigment preparations, printing inks and other coatings in which the pigment is incorporated.
  • the crude pigments formed in the synthesis are ground or comminuted.
  • dry grinding and wet grinding methods There are various known fine distribution methods for conversion of a crude pigment to pigment or pre-pigment form. In the dry and wet grinding methods, use of grinding bodies results in abrasion and hence introduction of extraneous substances into the product.
  • the pulverulent pigments are produced by reactions in the gas phase, in a flame, by sol-gel processes, in the plasma or by desublimation.
  • particles of small diameter have a particularly high tendency to agglomerate and therefore have to be stabilized.
  • the stabilization of the pigments is of great significance in the coatings industry, since pigments, being an important formulation constituent, determine the visual appearance and the physicochemical properties of a coating. In order that they can display their action to an optimal degree in the coating, they have to be homogeneously and finely distributed in the varnish during the dispersion process. The distribution has to be stabilized, in order that this state is maintained in the course of production, storage, processing and subsequent film formation. Recombination of the primary particles and aggregates can lead to formation of sediment, increasing viscosity, losses of gloss, inadequate colour depth, low hiding capacity, phase separation of the pigments and poor reproducibility of colour shades.
  • dispersants are generally used, in order thus to achieve maximum levels of filling. Being surface-active materials, the dispersants wet and cover the surface of the particles to be dispersed, and stabilize them against unwanted reagglomeration.
  • Pigments in aqueous pigment preparations are stabilized exclusively by wetting agents and dispersants, whereas dispersion in solventborne pigment preparations is often promoted by dispersing resins (Brock, Groteklaes, Mischke, Lehrbuch der Lacktechnologie [Coatings Technology], Vincentz Verlag Hannover 1998, p. 240).
  • the prior art discloses putting particulate pigments into a state from which they can be processed further as easily as possible.
  • WO 03/039716 describes an apparatus and a process for production of nanoparticulate pigments, in which a preliminary pigment material is evaporated and then condensed and collected in a collecting fluid.
  • the problem addressed by the present invention is that of modifying organic pigments in such a way that they can be easily dispersed and simultaneously have a high colour intensity, with no requirement for any additional grinding step by comparison with the production of the corresponding pigments.
  • wetting agents and dispersants can be classified in various ways.
  • the classifications of these are defined according to the chemical structure or are divided into ionic and nonionic products.
  • Other classifications are guided by the fields of use (aqueous and nonaqueous) or by the pigment group (organic and inorganic). Separation according to molecular size is also conceivable (low or high molecular weight). Owing to the complexity of amphiphilic substances which additionally also fulfil unique functions, it is not easy to develop a simple model concept.
  • the problem addressed by the present invention was therefore also that of determining or defining wetting agents and dispersants with which the modification of the organic pigments could be assured.
  • HSPs Hansen solubility parameters
  • Modified organic pigments according to Embodiment 1 characterized in that the interface-active compounds are chemical amphiphilic, ionic, nonionic compounds of low and/or high molecular weight.
  • Modified organic pigments according to Embodiment 1 characterized in that the interface-active compounds are polyether-modified fatty adds, polyether-modified fatty acid amide amines, polyether-modified amine derivatives, Jeffamine derivatives, polyether-modified oils and fats and derivatives thereof.
  • Modified organic pigments according to Embodiment 1 characterized in that the interface-active compounds are phosphorylated polyether derivatives, especially based on fatty alcohols.
  • Modified organic pigments according to Embodiment 1 characterized in that the interface-active compounds are polyether-modified styrene-maleic add copolymers and maleate resins.
  • Modified organic pigments according to Embodiment 1 or 2 characterized in that the compounds have one or more functionalities having an affinity for the pigment surface.
  • Modified organic pigments according to Embodiment 1 characterized in that the organic pigments are selected from the group of the azo, diazo, condensed azo, naphthol, metal complex, thioindigo, indanthrone, isoindanthrone, anthanthrone, anthraquinone, isodibenzanthrone, triphendioxazine, quinacridone, perylene, diketopyrrolopyrrole and phthalocyanine pigments.
  • the organic pigments are selected from the group of the azo, diazo, condensed azo, naphthol, metal complex, thioindigo, indanthrone, isoindanthrone, anthanthrone, anthraquinone, isodibenzanthrone, triphendioxazine, quinacridone, perylene, diketopyrrolopyrrole and phthalocyanine pigments.
  • Modified organic pigments according to any of the preceding Embodiments, characterized in that the modified pigments comprise 5% to 50% by weight, preferably 10% to 40% by weight, more preferably 14% to 35% by weight, of interface-active compounds based on 100% by weight of the modified organic pigments.
  • Process according to Embodiment 9 characterized in that the addition of the interface-active compounds is conducted in aqueous solution, preferably in alkaline solution.
  • Embodiments for production of pigment preparations are described.
  • FIG. 1 shows a schematic diagram of the Hansen space according to the invention.
  • FIG. 2 shows a schematic of a compound outside the Hansen space (unlabelled arrow).
  • FIG. 3 shows the dispersibility of the pigments according to the invention in water.
  • HSPs Hansen solubility parameters
  • the radius (distance) from the centre of the Hansen space can be calculated by means of the vector geometry.
  • Vector geometry also called “analytical geometry” is concerned with linear calculations in spaces and is known to those skilled in the art.
  • FIG. 1 shows a schematic diagram of the Hansen space according to the invention.
  • Pigments having interface-active compounds outside the Hansen space according to the invention do not have better colour quality.
  • solubility parameters according to Hansen is known to those skilled in the art and was elucidated in his work, “The Three Dimensional Solubility Parameter and Solvent Diffusion Coefficient, Their Importance In Surface Coating Formulation”, by Charles M. Hansen Danish Technical Press, Copenhagen, 1967.
  • HSPs Hansen solubility parameters
  • Hansen solubility parameters consist of a set of three values: a dispersion component ( ⁇ D), a polar component ( ⁇ P) and a hydrogen bond-forming component ( ⁇ H). These three components describe the forces that contribute to the cohesive energy density of a chemical compound, and enable a qualitative description beyond quantitative details of “hydrophobic”, “polar” or “lipophilic”.
  • the dissolution capacity of the materials can be determined and hence the Hansen space with its three Hansen solubility parameters can also be calculated.
  • the centre of the Hansen space here constitutes the optimal dissolution capacity of all materials.
  • the radius describes the limit of the Hansen space.
  • the interface-active compounds were each stirred in 32 solvents at 800 rpm at 20° C. for 20 minutes. The concentration was 0.25 g/5 ml of solvent. This procedure was conducted in a fully automated manner by means of the Formax High-Throughput Formulation System. Subsequently, the dissolution capacity of the interface-active compounds was determined in the respective solvents.
  • the dissolution capacity is assessed according to the following six-level scale:
  • HSPiP software version 5.0.0.4, programmed and sold by Prof. Steven J Abbott, Hiroshi Yamamoto and Charles Hansen (available via www.hansen-solubility.com). It calculates and determines the Hansen space using these data.
  • the interface-active compounds are chemical amphiphilic, ionic, nonionic compounds of low and/or high molecular weight that are within the above-detailed Hansen space according to the invention.
  • the interface-active compounds are polyether-modified fatty acids, polyether-modified fatty acid amide amines, polyether-modified amine derivatives, Jeffamine derivatives, polyether-modified oils and fats and derivatives thereof.
  • the interface-active compounds are phosphorylated polyether derivatives, especially based on fatty alcohols.
  • the interface-active compounds are maleate resins and polyether-modified styrene-maleic acid copolymers.
  • Maleate resins are Diels-Alder adducts of rosins with maleic acid or fumaric acid, which may also be wholly or partly esterified with polyhydric alcohols.
  • the interface-active compounds are polyesters modified with groups having pigment affinity.
  • the interface-active compounds are nonionic ethoxylated sugar surfactants.
  • polyoxyethylene sorbitan monolaurate More preferably, they are polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monopalmitate, polyoxyethylene sorbitan monostearate, polyoxyethylene sorbitan monooleate, polyoxyethylene sorbitan tristearate.
  • the interface-active compounds have one or more functionalities having an affinity for a pigment surface.
  • Suitable interface-active compounds having the required Hansen parameters are the products available from Evonik Industries AG, for example TEGO® Dispers 652, TEGO® Dispers 655, TEGO® Dispers 673, TEGO® Dispers 740W, TEGO® Dispers 750.
  • the Erkamar 3260 product from Robert Kraemer GmbH & Co. KG is also suitable.
  • the organic pigments are preferably selected from the group of the azo, diazo, condensed azo, naphthol, metal complex, thioindigo, indanthrone, isoindanthrone, anthanthrone, anthraquinone, isodibenzanthrone, triphendioxazine, quinacridone, perylene, diketopyrrolopyrrole and phthalocyanine pigments.
  • Naphthol AS pigments are conventionally produced in batch processes. For the yield, coloristic quality and consistency of quality, it is necessary that the process parameters such as temperature, time, commixing and colourant concentration and the suspension concentration are maintained and controlled. Further difficulties also arise in batch processes on scale-up from laboratory scale to the industrial scale, since the tank and stirrer geometries or transfers of heat have a great effect on the primary particle size, grain size distribution.
  • Naphthol AS pigments are of particular industrial interest since they usually attain high colour intensities and cover the magenta region of the process colour set. In addition, they have good lightfastness.
  • DE 102004019560 A1 DE 602006017431 D1 describe the production of naphthol AS pigments and the use thereof in dispersions.
  • the modified organic pigments comprise 2% to 70% by weight, preferably 5% to 50% by weight, more preferably 15% to 35% by weight, of interface-active compounds based on 100% by weight of the modified organic pigments.
  • the invention further provides the process for producing the modified organic pigments, wherein the interface-active compounds within the Hansen space according to the invention are added during the production of the organic pigments.
  • the interface-active compounds can be added at any time during the production of the organic pigments.
  • the conventional production process for organic pigments is divided into the following component steps:
  • the addition of the interface-active compounds takes place during the synthesis of the crude pigments, after the synthesis of the crude pigments or after the workup of the crude pigments.
  • the modification preferably precedes the drying of the crude pigments.
  • the process according to the invention enabled the production of organic pigments with narrow particle size distribution.
  • the modified organic pigments have improved dispersion properties. It is suspected that the interface-active compounds interact with the surface of the pigments owing to van der Waals forces. The interaction is so stable that it was possible to reduce or prevent agglomeration of the pigments.
  • the addition of the interface-active compounds is conducted in aqueous solution, preferably in alkaline solution at a pH of 8 to 9.
  • the weight ratio of the interface-active compounds to the 4-aminobenzamide is from 0.3:1 to 10:1, preferably 0.5:1 to 5:1, more preferably 0.35:1 to 3.5:1.
  • the invention also provides for the use of the modified organic pigments according to the invention for production of paints, varnishes, printing inks, coating materials, floor coatings, potting compounds and filling compounds.
  • Suitable paint systems into which the modified organic pigments according to the invention can be incorporated are any solventborne or aqueously formulated one-component or two-component paint systems (1K or 2K), but also solvent-free systems.
  • Examples of 1K paint systems are those based on alkyd, acrylate, styrene acrylate, epoxy, polyvinyl acetate, polyester or polyurethane binders. Any kind of curing is possible, for example by oxidative drying, physical drying, self-crosslinking, UV or electron beam curing or crosslinking by baking.
  • 2K paint systems crosslink as a result of the addition of at least one hardener component.
  • crosslinking mechanisms are combined in order to achieve a better shelf life. All combinations of curing mechanisms are permissible here.
  • hydroxyl-containing polyesters or polyacrylate resins can be crosslinked with isocyanates or blocked isocyanates or melamine resins as 2K systems.
  • isocyanates or blocked isocyanates or melamine resins as 2K systems.
  • epoxy systems where the epoxy binder is reacted with an amine hardener.
  • the modified organic pigments according to the invention can be used in pigment pastes, coating materials, printing inks and/or printing varnishes in a concentration of 0.01% to 90.0% by weight, preferably of 0.5% to 35% by weight, and more preferably of 1% to 25% by weight, based on the application medium.
  • Parameters or measurements are preferably determined using the methods described hereinbelow. In particular, these methods were used in the examples of the present intellectual property right.
  • the tinted varnishes were applied with a spiral coating bar (100 ⁇ m, from TQC GmbH) to test charts (for example from Leneta, Opacity charts, Form 2A).
  • the colour intensity was obtained after drying at 50° C. for 24 h was subjected to a colour measurement.
  • the colour of the paint surfaces was measured with an X-Rite instrument (model: X-Rite SP 60).
  • CIE-Lab system is useful as a three-dimensional system for quantitative description of the colour loci. In this system, the colours green (negative a* values) and red (positive a* values) are plotted on one axis, and the colours blue (negative b* values) and yellow (positive b* values) on the axis arranged at right angles thereto.
  • the two axes cross at the achromatic point.
  • the CIE-Lab system can be used to describe not just colour loci but also colour separations via the specification of the three coordinates.
  • Table 3 also shows the coordinates of the comparative example VM with a distance from the centre outside the Hansen space.
  • the distance from the centre of the Hansen space can be calculated by means of the vector geometry.
  • Vector geometry (also called “analytical geometry”) is concerned with linear calculations in spaces and is known to those skilled in the art.
  • FIG. 2 shows a schematic of a compound outside the Hansen space (unlabelled arrow).
  • the arrow labelled “r” shows the radius of the Hansen space from the centre.
  • the suspension formed was stirred at 70° C. for a further 60 min. 186.4 g of NaOH (10%) were used to adjust it to pH>7.
  • the interface-active compound according to the invention was added to the mixture in the weight ratio specified in Table 4 and Table 5.
  • the modified pigment according to the invention was coarsely comminuted in a knife mill (Retsch Grindomix GM200) at 10 000 rpm for 10 seconds.
  • the interface-active compounds according to the invention were added with the weight ratio specified in Table 4 or 5 to a solution consisting of 33.33 g of 2-methoxy-3-hydroxy-2-naphthanilide (for PR266) or 34.93 g of N-(2-ethoxyphenyl)-3-hydroxy-2-naphthalenecarboxamide (for PR170), 50 g of NaOH (10%), 100 g of ethanol, 8.33 g of sodium nitrite and 25 g of demineralized water.
  • This mixture was added dropwise at 5° C. over a period of 120 min to a solution consisting of 15.47 g of 4-aminobenzamide, 166.67 g of demineralized water, 28.87 g of conc. HCl and 16.67 g of sodium acetate.
  • the suspension formed was stirred at 70° C. for a further 60 min.
  • the mixture was alkalized with 62.13 g of 10% NaOH.
  • the modified pigment according to the invention was coarsely comminuted in a knife mill (Retsch Grindomix GM200) at 10 000 rpm for 10 seconds.
  • the suspension formed was stirred at 70° C. for a further 60 min.
  • the interface-active compound according to the invention was added to the filtercake in the weight ratio according to Table 4 or 5 and it was homogenized for 30 minutes. 10% HCl was used for acidification to a pH of 5, followed by drying in an air circulation oven at 70° C.
  • the modified pigment according to the invention was coarsely comminuted in a knife mill (Retsch Grindomix GM200) at 10 000 rpm for 10 seconds.
  • Comparative pigments VP2 and VP4 were produced without addition of interface-active compound.
  • Comparative pigments VP1 and VP3 were prepared analogously to the production processes specified in Tables 4 and 5 with addition of VM (interface-active compound outside the Hansen space). Comparative pigments VP1 and VP3 could not be filtered off.
  • the pigments were used in a water-thinnable white paint, in a concentrate and in a 2-component PU varnish.
  • the paints and varnishes are compared with one another on the basis of colour intensity.
  • composition was applied to test charts (Leneta charts) with a spiral coating bar (100 ⁇ m) and provided for colorimetry.
  • Table 7 shows the colour values measured. What is desired here is a minimum differential in the colour intensity F* between the paints with low shear energy and those with high shear energy. It is found that the inventive paints (L1, L3, L5) comprising the inventive pigments (P1, P3, P5) have a smaller differential than the comparative paints (VL2) comprising the comparative pigments (VP2).
  • the differential gives a statement as to the dispersibility of the pigments. It has been found that the pigments according to the invention do not require a high energy input for the paint to receive a good to very good colour intensity.
  • pigments are processed to a concentrate in order to enable flexible and variable production by holding various shades in stock.
  • inventive pigments and comparative pigments were therefore tested as concentrates with low and high shear forces:
  • compositions produced were applied as in the example of the water-thinnable white paint and evaluated by colorimetry.
  • inventive concentrates comprising the inventive pigments (P10, P14, P15) exhibited an elevated colour intensity F* when relatively low shear energies were used compared to the comparative concentrate (VK4) comprising the comparative pigment (VP4).
  • inventive pigment or comparative pigment To this mixture were added 2.5 g of inventive pigment or comparative pigment, which were then stirred in at a shear velocity of 3 m/s by means of a DISPERMAT CV from Getzmann for 10 minutes. After application and a flash-off time of 10 minutes at room temperature, followed by forced drying at 60° C. for 30 minutes, the colorimetric analysis was effected.
  • inventive pigment or comparative pigment were added to 85.5 g of the 2K polyurethane varnish produced, and dispersion was effected with a universal agitator (Hausschild Engineering, DAC 150 Dual Asymmetric Centrifuge) together with 2 mm glass beads in 250 ml screwtop glass bottles for 120 min. The glass beads were subsequently removed.
  • a universal agitator Hausschild Engineering, DAC 150 Dual Asymmetric Centrifuge
  • the PU varnishes (L10, L14, L16) comprising the inventive pigments P10, P14 and P16 had higher colour intensity than that of the comparative PU varnishes (VL4) comprising the comparative pigment VP4. More particularly, it can be inferred from Table 9 that the pigments according to the invention had good to very good dispersibility, since there were barely any perceptible differences in colour intensity between a varnish with high and low shear energy.
  • FIG. 3 shows the dispersibility of the pigments according to the invention in water.
  • the comparative pigment VP2 (without interface-active compound) was added to water.
  • the comparative pigment VP2 floated on the surface of the water.
  • VP2 and the interface-active compound M6 were added to water.
  • the middle beaker showed the modified pigment P6 according to the invention in water. Without stirring, it already had good dispersibility in water.

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  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Dispersion Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Paints Or Removers (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Pigments, Carbon Blacks, Or Wood Stains (AREA)
US16/044,960 2017-07-26 2018-07-25 Modified pigments and use thereof Abandoned US20190031880A1 (en)

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EP17183262.9 2017-07-26
EP17183262.9A EP3434737B1 (de) 2017-07-26 2017-07-26 Modifizierte pigmente und ihre verwendung

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EP (1) EP3434737B1 (ja)
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CN (1) CN109306196A (ja)
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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10752801B2 (en) 2017-12-27 2020-08-25 Evonik Operations Gmbh Wetting agents and dispersants having rheological character
US11236204B2 (en) 2019-05-28 2022-02-01 Evonik Operations Gmbh Production of SiOC-bonded polyether siloxanes
US11261298B2 (en) 2019-05-28 2022-03-01 Evonik Operations Gmbh Tailored SiOC-based polyethersiloxanes
US11286366B2 (en) 2019-05-28 2022-03-29 Evonik Operations Gmbh Process for recycling silicones
US11377523B2 (en) 2019-05-28 2022-07-05 Evonik Operations Gmbh Process for producing non-cyclic alkoxy-functional polysiloxanes
US11420985B2 (en) 2019-05-28 2022-08-23 Evonik Operations Gmbh Acetoxy systems
US11472822B2 (en) 2019-05-28 2022-10-18 Evonik Operations Gmbh Process for purifying acetoxysiloxanes

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EP3744762A1 (de) 2019-05-28 2020-12-02 Evonik Operations GmbH Verfahren zur herstellung von polyoxyalkylen polysiloxan blockpolymerisaten
CN110078930A (zh) * 2019-05-29 2019-08-02 天津赫普菲乐新材料有限公司 一种梳形改性苯乙烯-羧酸共聚物及其应用

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KR100532107B1 (ko) * 2003-08-09 2005-11-29 삼성전자주식회사 아조 모이어티를 포함하는 자가 분산형 금속착물 착색제
DE10351737A1 (de) * 2003-11-06 2005-06-16 Degussa Ag Ruß
EP1566413B1 (de) * 2004-02-20 2006-04-19 Goldschmidt GmbH Verfahren zur Herstellung von homogenen, lagerstabilen Pasten, Farben, Lacken unter Mitverwendung ionischer Flüssigkeiten als Dispergierhilfsmittel
KR20060130094A (ko) * 2004-04-02 2006-12-18 다이스타 텍스틸파르벤 게엠베하 운트 콤파니 도이칠란트 카게 디지털 텍스타일 프린팅용 고내광성 잉크
DE102004019560A1 (de) 2004-04-22 2005-11-10 Clariant Gmbh Hochreine Naphthol AS-Pigmente
ES2403632T3 (es) 2005-11-28 2013-05-20 Agfa Graphics N.V. Dispersiones de pigmento no acuosas que contienen sinergistas de dispersión específicos
US7642282B2 (en) * 2007-01-19 2010-01-05 Milliken & Company Whitening agents for cellulosic substrates
DE102007018812A1 (de) * 2007-04-20 2008-10-23 Evonik Goldschmidt Gmbh Polyether enthaltende Dispergier- und Emulgierharze
PL2591057T3 (pl) * 2010-07-09 2019-12-31 Evonik Röhm Gmbh Wodna płynna farba zawierająca termostabilne dodatki dyspergujące do barwienia polimetakrylanów
DE102010039140A1 (de) * 2010-08-10 2012-02-16 Evonik Goldschmidt Gmbh Dispergiermittel und Verfahren zu deren Herstellung
JP6071439B2 (ja) * 2011-11-30 2017-02-01 キヤノン株式会社 フタロシアニン結晶の製造方法、および電子写真感光体の製造方法
JP6077772B2 (ja) * 2012-07-17 2017-02-08 理想科学工業株式会社 着色樹脂粒子分散体及びインク
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US9815986B2 (en) * 2013-09-27 2017-11-14 Dic Corporation Methods for producing aqueous pigment dispersion liquid and water-based ink for ink jet recording
EP2868720A1 (en) * 2013-11-01 2015-05-06 Siegwerk Druckfarben AG & Co. KGaA Printing ink with nitrated lignin ester as binder component
EP3085746A4 (en) * 2013-12-19 2017-07-12 DIC Corporation Aqueous pigment composition and pigment ink
JP6148626B2 (ja) * 2014-01-16 2017-06-14 理想科学工業株式会社 着色樹脂粒子分散体及びインクジェットインク
JP6249785B2 (ja) * 2014-01-16 2017-12-20 理想科学工業株式会社 着色樹脂粒子分散体及びインクジェットインク
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US10287448B2 (en) * 2016-07-08 2019-05-14 Evonik Degussa Gmbh Universal pigment preparation

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10752801B2 (en) 2017-12-27 2020-08-25 Evonik Operations Gmbh Wetting agents and dispersants having rheological character
US11236204B2 (en) 2019-05-28 2022-02-01 Evonik Operations Gmbh Production of SiOC-bonded polyether siloxanes
US11261298B2 (en) 2019-05-28 2022-03-01 Evonik Operations Gmbh Tailored SiOC-based polyethersiloxanes
US11286366B2 (en) 2019-05-28 2022-03-29 Evonik Operations Gmbh Process for recycling silicones
US11377523B2 (en) 2019-05-28 2022-07-05 Evonik Operations Gmbh Process for producing non-cyclic alkoxy-functional polysiloxanes
US11420985B2 (en) 2019-05-28 2022-08-23 Evonik Operations Gmbh Acetoxy systems
US11472822B2 (en) 2019-05-28 2022-10-18 Evonik Operations Gmbh Process for purifying acetoxysiloxanes

Also Published As

Publication number Publication date
EP3434737B1 (de) 2023-01-04
EP3434737A1 (de) 2019-01-30
JP2019026835A (ja) 2019-02-21
US20210163751A1 (en) 2021-06-03
CN109306196A (zh) 2019-02-05
ES2940217T3 (es) 2023-05-04
DK3434737T3 (da) 2023-03-27
JP7254458B2 (ja) 2023-04-10

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