EP3313941A1 - Mélanges de pigments naphtol as - Google Patents

Mélanges de pigments naphtol as

Info

Publication number
EP3313941A1
EP3313941A1 EP16735833.2A EP16735833A EP3313941A1 EP 3313941 A1 EP3313941 A1 EP 3313941A1 EP 16735833 A EP16735833 A EP 16735833A EP 3313941 A1 EP3313941 A1 EP 3313941A1
Authority
EP
European Patent Office
Prior art keywords
alkylcarbamoyl
alkyl
hydrogen
formula
azopigmentmischung
Prior art date
Legal status (The legal status 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 status listed.)
Withdrawn
Application number
EP16735833.2A
Other languages
German (de)
English (en)
Inventor
Ulrike Rohr
Joachim Eichhorn
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Avient Switzerland GmbH
Original Assignee
Clariant Plastics and Coatings Ltd
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 Clariant Plastics and Coatings Ltd filed Critical Clariant Plastics and Coatings Ltd
Publication of EP3313941A1 publication Critical patent/EP3313941A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • C09B67/0046—Mixtures of two or more azo dyes
    • C09B67/0051—Mixtures of two or more azo dyes mixture of two or more monoazo dyes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/22—Compounds containing nitrogen bound to another nitrogen atom
    • C08K5/23—Azo-compounds
    • 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
    • C09D7/41—Organic pigments; Organic dyes
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
    • G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K2201/00—Specific properties of additives
    • C08K2201/014—Additives containing two or more different additives of the same subgroup in C08K
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0041—Optical brightening agents, organic pigments

Definitions

  • the present invention is in the field of azo pigments.
  • Naphthol AS pigments are of particular technical interest, since these usually achieve high color strengths and the magenta range of
  • Quinacridone pigments such as PR 122, can be achieved, which then has an adverse effect on the color strength and the process costs.
  • the present invention now describes mixtures of naphthol AS pigments which, surprisingly, do not exhibit this disadvantage and whose dyeings have a brilliant magenta hue with simultaneously high color strength and transparency and low costs.
  • the invention relates to mixtures of naphthol AS pigments, each containing at least one naphthol AS pigment of the formulas (Ia) and (Ib),
  • X 1 , X 3 carbamoyl, C 1 -C 4 -alkylcarbamoyl, di (C 1 -C 4) -alkylcarbamoyl, sulfamoyl,
  • X 2 , X 4 are hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, halogen or nitro;
  • Y 1 , Y 2 are hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, halogen or C 1 -C 4 -alkoxycarbonyl; and
  • Z 1 , Z 2 is hydrogen, phenyl, naphthyl, benzimidazolonyl, substituted phenyl or substituted naphthyl, where the substituents 1, 2, 3 or 4 in the number and selected from the group halogen, nitro, cyano, C 1 -C 4
  • X 1 , X 3 preferably carbamoyl, C 1 -C 4 -alkylcarbamoyl, di (C 1 -C 4) -
  • Alkylcarbamoyl particularly preferably carbamoyl, Ci-C2-alkylcarbamoyl or di (Ci-C2) -alkylcarbamoyl.
  • X 2 , X 4 are preferably hydrogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy, especially
  • Y 1 , Y 2 is preferably C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy, particularly preferably methyl,
  • Z 1 , Z 2 is preferably hydrogen, phenyl, or nitro, cyano, halogen, C 1 -C 4 -alkyl and / or C 1 -C 4 -alkoxy-substituted phenyl, particularly preferably phenyl or with nitro, methyl, ethyl, methoxy and / or ethoxy
  • Preferred for the purposes of the present invention are mixtures of naphthol AS pigments, which in each case contain at least one naphthol AS pigment of the formulas (IIa) and (IIb),
  • X 2 is hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, halogen or nitro;
  • Y is hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, halogen or C 1 -C 4 -alkyl
  • Z 1 , Z 2 is hydrogen, phenyl, naphthyl, benzimidazolonyl, substituted phenyl or substituted naphthyl, wherein the substituents 1, 2, 3 or 4 in the number and selected from the group halogen, nitro, cyano, C 1 -C 4 alkoxycarbonyl, carbamoyl , C 1 -C 4 -alkylcarbamoyl, di (C 1 -C 4) -alkylcarbamoyl, phenylcarbamoyl, sulfamoyl, phenylsulfamoyl, C 1 -C 4 -alkylsulfamoyl, di (C 1 -C 4) -alkylsulfamoyl, C 1 -C 4 -acylamino, C 1 -C 4 -alkyl and C 1 -C 4 -alkylcarbamoyl -C4-
  • halogen is preferably F, Cl or Br, especially Cl.
  • the invention relates to mixtures of naphthol AS pigments, each of which contains at least one naphthol AS pigment of the formulas (IIIa) and (IIIb),
  • X 1 is carbamoyl, C 1 -C 2 -alkylcarbamoyl or di (C 1 -C 2) -alkylcarbamoyl;
  • Y is methyl, methoxy, ethyl or ethoxy
  • Z 1 is phenyl or one, two or three radicals from the group
  • Z 2 have the meaning nitrophenyl or cyanophenyl.
  • naphthol AS pigments each containing at least one naphthol AS pigment of the above formulas (IIIa) and (IIIb), wherein
  • X 1 is carbamoyl, methylcarbamoyl or ethylcarbamoyl
  • Y is methoxy or ethoxy
  • Z 1 is methylphenyl, ethylphenyl, methoxyphenyl or
  • Z 2 have the meaning nitrophenyl or cyanophenyl.
  • naphthol AS pigments each containing at least one naphthol AS pigment of the above formulas (IIIa) and (IIIb), wherein
  • X 1 is carbamoyl or methylcarbamoyl; Y is methoxy;
  • Z 1 is methylphenyl, in particular o-methylphenyl
  • Z 2 has the meaning nitrophenyl, in particular m-nitrophenyl.
  • the pigment mixtures according to the invention expediently contain 1 to 99% by weight of a component of the formula (Ia), (IIa) or (IIIa) and 99 to
  • a component of the formula (Ib), (IIb) or (IIIb) particularly preferably 10 to 90% by weight of a component of the formula (Ia), (IIa) or (IIIa) and 90 to 10% by weight .-% of a component of formula (Ib), (IIb) or (IIIb), most preferably 25 to 75 wt .-% of a component of formula (la), (IIa) or (IIIa) and 75 to 25 wt.
  • the pigment mixtures according to the invention optionally contain one or more additional colorants of the general formula (IV) in proportions of up to 10% by weight, for example from 0.1 to 10% by weight, based on the total weight of the pigment mixture,
  • X 1 , X 2 , Y has one of the meanings given above and M is hydrogen, an alkali metal, an alkaline earth metal or for
  • the pigment mixtures according to the invention may optionally contain one or more residual couplers from the group of the ⁇ -naphthol derivatives of the general formulas (VIA) and / or (VIb) in proportions of up to 10% by weight, for example from 0.1 to 10% by weight, based on the total weight of the pigment mixture, of
  • Z 1 and Z 2 have one of the meanings given above.
  • the pigment mixtures according to the invention can be prepared
  • the resulting pigment suspension can be filtered and the resulting moist presscake is expediently dried to constant weight.
  • the pigment mixtures according to the invention can also be prepared by co-sublimation in vacuo or by mixing the separately prepared
  • Ether alcohols or carboxylic acids such as acetic acid, trifluoroacetic acid or dichloroacetic acid.
  • the azo coupling reaction is preferably carried out in aqueous solution or suspension, and preferably at a pH between 3 and 9, but it can also be organic solvents, optionally used in admixture with water, for example alcohols having 1 to 10 carbon atoms, such as methanol , Ethanol, n-propanol, isopropanol, butanols, such as n-butanol, sec-butanol, tert-butanol, pentanols, such as n-pentanol, 2-methyl-2- butanol, hexanols such as 2-methyl-2-pentanol, 3-methyl-3-pentanol, heptanols such as 2-methyl-2-hexanol, 3-ethyl-3-pentanol, octanols, such as 2,4,4-trimethyl 2-pentanol, cyclohexanol; or glycols, such as ethylene glyco
  • Ether such as methyl isobutyl ether, tetrahydrofuran or
  • Glycol ethers such as monomethyl or monoethyl ethers of ethylene or propylene glycol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, butyl glycols or methoxybutanol; Ketones, such as acetone,
  • aliphatic acid amides such as formamide, dimethylformamide, N-methylacetamide or ⁇ , ⁇ -dimethylacetamide; Urea derivatives, such as tetramethylurea; or cyclic carboxylic acid amides, such as N-methylpyrrolidone, valero or caprolactam; Esters, such as carboxylic acid C 1 -C 6 -alkyl esters, such as butyl formate,
  • Ethyl acetate or propionic acid propyl ester or carboxylic acid Ci-Cö- glycol ester; or glycol ether acetates such as 1-methoxy-2-propyl acetate; or
  • Phthalic or benzoic acid C 1 -C 6 -alkyl esters, such as ethyl benzoate; cyclic esters such as caprolactone; Nitriles, such as acetonitrile or benzonitrile;
  • aliphatic or aromatic hydrocarbons such as cyclohexane or benzene; or benzene substituted by alkyl, alkoxy, nitro or halogen, such as toluene, xylenes, ethylbenzene, anisole, nitrobenzene, chlorobenzene, o-dichlorobenzene,
  • the solvents mentioned can also be used as mixtures. Preferably water-miscible solvents are used.
  • An optional finish following the pigment synthesis includes picking up the prepared naphthol-AS pigment mixture, either directly from the synthesis or after intermediate isolation e.g. B. as a press cake
  • organic solvents typically about 5 to 30 wt .-% solids content
  • Preferred solvents are C 3 -C 4 -alcohols, glycol ethers and chlorinated benzenes, for example isopropanol, isobutanol, butoxyethanol, ortho-dichlorobenzene, or a mixture thereof.
  • the amount of the solvent is preferably 1 to 30% by volume,
  • the pigment finish is preferably at a temperature between 20 ° C and 150 ° C, in particular between 40 ° C and 90 ° C, optionally under pressure, and preferably for 0.1 to 2 hours, in particular 0.25 to 1 hours, and preferred carried out at atmospheric pressure and preferably with stirring.
  • ordinary stirring devices such as B. Laboratory stirrers in question.
  • the solvent-treated pigment suspension is filtered and washed.
  • Dispersibility, brilliance, hue or contrast value can be the
  • Pigment mixtures according to the invention are also subjected to a fine distribution.
  • the desired particle size distribution depends on the desired field of application. If the colorant composition according to the invention is used, for example, in the form of a dispersed colorant in a mill base for color filters, it is advantageous to adjust a small primary particle size beforehand in a suitable manner. Particularly suitable for this application are primary particle sizes of less than 60 nm, preferably less than 40 nm in the d50 value. It is also advantageous to set a narrow particle size distribution.
  • the particle size distribution after reduction is preferably approximated to a Gaussian distribution in which the standard deviation sigma is preferably less than 30 nm, more preferably less than 20 nm.
  • the standard deviations are between 5 and 30 nm, preferably between 6 and 25 nm, in particular between 7 and 20 nm.
  • the standard deviation sigma ( ⁇ ) corresponds to the positive square root of the variance.
  • the variance v is the sum of the squared deviations from
  • Color filter application is advantageous if the d95 value of the comminuted particles is less than or equal to 70 nm.
  • the length to width ratio of the comminuted particles for the color filter application is preferably between 2: 1 and 1: 1.
  • Solvent used. Come as a crystalline inorganic salt
  • aluminum sulfate, sodium sulfate, calcium chloride, potassium chloride or sodium chloride preferably sodium sulfate, sodium chloride and
  • Suitable organic solvents are, for example, ketones, esters, amides, sulfones, sulfoxides, nitro compounds, mono-, bis- or tris-hydroxy-C 2 -C 12 -alkanes which may be substituted by C 1 -C 8 -alkyl and one or more hydroxy groups consideration.
  • Particularly preferred are water-miscible high-boiling organic solvents based on monomeric, oligomeric and polymeric C 2 -C 3 -alkylene glycols, such as. B. diethylene glycol, diethylene glycol monomethyl and ethyl ether, triethylene glycol,
  • the weight ratio between the inorganic salt and the compound of the formula (I) is preferably (2 to 10) to 1, especially (3 to 7) to 1.
  • the weight ratio between the organic solvent and the inorganic salt is preferably (1 ml: 10 g) to (2 ml: 7 g).
  • the weight ratio between the organic solvent and the sum of inorganic salt and the colorant composition of the present invention is preferably (1 ml: 2 g) to (1 ml: 10 g).
  • the temperature during kneading can be between 40 and 140 ° C,
  • the kneading time is expediently 4 hours to 32 hours, preferably 8 hours to 20 hours.
  • the inorganic salt and the organic solvent are expediently removed by washing with water and the crushed colorants thus obtained are dried by conventional methods.
  • the material obtained after the fine distribution may optionally be used for the color filter application as a suspension, filter cake or dry material
  • Solvent after-treatment finishing treatment
  • finishing treatment are subjected to obtain a more homogeneous particle shape, without significantly increasing the particle size.
  • Preference is given to the use of steam-volatile
  • Solvents such as alcohols and aromatic solvents, particularly preferably branched or unbranched C 1 -C 6 -alcohols, toluene, xylene,
  • Chlorobenzene, dichlorobenzene, nitrotoluene or nitrobenzene usually under elevated
  • auxiliaries such as, for example, surfactants, pigmentary and nonpigmentary dispersants, fillers, setting agents, resins, waxes, defoamers, anti-dust agents, extenders, colorants for
  • Light stabilizers or a combination thereof can be used.
  • the addition of the adjuvant can be carried out at any time before, during or after the reaction / synthesis or, if appropriate, fine dispersion, all at once or in several portions.
  • the aids can be added, for example, directly to the solutions or suspensions of the reactants, but also during the reaction in liquid, dissolved or suspended form.
  • the total amount of auxiliaries added may be from 0 to 40% by weight, preferably from 1 to 30% by weight, particularly preferably from 2.5 to 25% by weight, based on the total weight of the pigment mixture plus auxiliary.
  • Suitable surfactants are anionic or anionic, cationic or cationic and nonionic substances or mixtures of these agents.
  • buffer solutions may also be added, preferably organic acids and their salts, such as
  • Citric acid / citrate buffer or of inorganic acids and their salts, such as phosphoric acid / phosphate buffer or
  • Carbonic acid / bicarbonate or carbonate buffer Carbonic acid / bicarbonate or carbonate buffer.
  • the pigment mixtures according to the invention can be combined / mixed with other organic and / or inorganic color pigments and / or with dyes.
  • Organic color pigments can for this purpose be selected from the group of azo and / or polycyclic pigments, eg. Yellow pigments, such as C.I.
  • red / magenta pigments such as Pigment Red 57, P.R. 48, P.R. 122, P.R. 146, P.R. 147, P.R. 269, P.R. 154, P.R. 185, P.R. 184, P.R. 192, P.R. 202, P.R. 207, P.R. 206, P.R. 209 or P.R. 254; and violet pigments such as Pigment Violet 19, P.V. 23, P.V. 29, P.V. 35 or P.V. 37, P.V. 57 and also blue pigments, such as Pigment Blue 15, P.B. 60 or P.B. 80th
  • Preferred colorants for shading are quinacridone pigments or a
  • Naphthol AS pigment is different from the compound of formula (Ia) and (Ib).
  • the following pigments in mixtures with the compositions according to the invention can be used as further components in the color film for the red area in addition to the abovementioned red / magenta pigments: C.I. Pigment Red 149, P.R. 166, P.R. 168, P.R. 177, P.R. 242, P.R. 264, as well as further diketopyrrolopyrroles, in particular brominated diketopyrrolopyrroles as described in WO2009 / 1441 15A1, as well as diketopyrrolo-pyrrole compositions, as described in WO2009 / 049736A2, EP2146230B1 and
  • Diketopyrrolo-pyrrole compositions are water-soluble dyes from the group of direct, reactive and acid dyes, and also dyes from the series of solvent dyes (solvent dyes), disperse dyestuffs and vat dyes (Vat Dyes).
  • Chroma which makes the pigment mixtures according to the invention attractive for many industrial applications.
  • they can be used for pigmenting high molecular weight organic materials of natural or synthetic origin, for example of plastics, resins, paints,
  • the naphthol according to the invention is used
  • AS pigment mixtures usually in an amount of 0.05 to 30 wt .-%
  • hydrochloric acid 31%
  • the precipitated hydrochloride is made by adding 179 g of sodium nitrite solution (40%) over 15 to
  • the clarified diazonium salt solution from a1) is initially charged, adjusted to pH 4.3 to 4.5 by adding about 38 g of sodium acetate (in the form of a 4N solution) and cooled to 10 ° C. Thereafter, with stirring, the coupler solution from a2) is metered in over the course of 1 to 1.5 h, the pH being kept at 4.8 to 5 by simultaneous addition of a total of about 190 g of hydrochloric acid (31% strength) , Subsequently, about 2.5 to 3 h or until the disappearance of
  • Diazo component stirred at RT to 30 ° C and pH 5 to 6. After completion of the coupling reaction is heated for a further 1 h to about 50 ° C, then filtered and washed with water. After drying and grinding, 480 g of the bluish dark red pigment mixture according to the invention are obtained which contain the
  • Example 36 The pigment mixtures according to the invention of Examples 2 to 35 show the desired bluish-red magenta hue and at the same time a high brilliance.
  • Example 36 The pigment mixtures according to the invention of Examples 2 to 35 show the desired bluish-red magenta hue and at the same time a high brilliance.
  • a pigment of the formula (13) and 30 g of a pigment of the formula (2) are added in each case in the form of a moist presscake in 1000 g of water and homogenized by 1-hour stirring at RT to 95 ° C. After filtration, drying and grinding, 100 g of a
  • a reaction mixture obtained according to Example 1a or 1b containing 480 g of a mixture of the pigments of the formulas (1) and (2) in a mass ratio of 65: 35 is treated with 72 g of C.I. Pigment Red 269 of the formula
  • a reaction mixture obtained according to Example 1 a or 1 b which contains 480 g of a mixture of the pigments of the formulas (1) and (2) in a mass ratio of 65: 35, with 96 g C.I. Pigment Red 122 with the formula
  • the chroma and the hue angle were determined in an alkyd paint (0.5%).
  • the chroma C is the
  • pigment mixtures according to the invention preferably between 58 and 74 (74> C> 58) and more preferably between 60 and 70 (70> C> 60).
  • the hue h is preferably between 345 and 360 or between 0 and 15, and particularly preferably between 350 and 360 or between 0 and 10 (CIELAB coordinates).
  • the varnish thus obtained is transferred by means of a handcoater to a film-drawing apparatus and drawn up in 100 ⁇ m wet film thickness onto a test card (chromo cardboard, white, cast-coated on one side, 300 g / m 2 , size 100 ⁇ 230 mm).
  • the lacquer card is first dried at room temperature for 15 minutes and then dried in a drying oven at 60 ° C. for 60 minutes.
  • the values for chroma (C) and hue (h) are measured by means of a D65 standard light lamp at an observation angle of 10 °, for example with a Datacolor - Spectraflash - SF600 - PLUS CT spectrophotometer, in accordance with DIN 5033-7, ISO 7724- 2 measured.
  • 15.0 g of the pigment mixture according to the invention according to Example 1 are in a paint shaker beaker with 52.1 g of methoxypropyl acetate (PGMEA), 5.0 g n-butanol and 16.0 g of Disperbyk ® 2001 (BYK-Chemie, polymeric dispersing aid - solution) and 1 1, 9 g Ripoxy ® SPC-2000 (Showa high polymers Japan, 38% strength polymeric binder solution) with stirring.
  • PGMEA methoxypropyl acetate
  • Disperbyk ® 2001 BYK-Chemie, polymeric dispersing aid - solution
  • 1 1, 9 g Ripoxy ® SPC-2000 Showa high polymers Japan, 38% strength polymeric binder solution
  • the obtained binder-containing pigment dispersion is determined by means of a
  • the layer thickness is in each case about 1 to 2 micrometers.
  • the glass plates are allowed to flash and then dried for 10 min at 80 ° C in a convection oven (Binder). From the glass plates are the values of the color coordinates (x, y, Y, and CIELAB, Spectrophotometer Datacolor 650, light C) , 2 ° observer), measured transmission curves (ditto) and contrast values (Contrast Tester Tsubosaka CT-1). From the determined contrast ratios and the measured x-values for the glass plates of each sample a mathematical straight line is calculated. This straight line describes the dependence of the contrast value on the color coordinate x. Using the linear equation, the contrast ratio is calculated at a defined x-value and compared with the contrast ratio of the comparative sample at this x-value.
  • the Mill Base and color dispersion is analogous as in the case of Application example COF-1 produced. However, none are used
  • magenta quinacridone pigment for use in color filters (Hostaperm Red EG-COF, C.I. Pigment Red 209, Clariant Products Germany GmbH).
  • the relative contrast ratio KV refers to the coloration of the
  • the value x denotes the color coordinate in the CIE Yxy standard color space.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Optical Filters (AREA)
  • Paints Or Removers (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)

Abstract

L'invention concerne des mélanges de pigments azoïques comprenant au moins un pigment azoïque de formule (la) et au moins un pigment azoïque de formule (Ib), dans lesquelles X1, X3 représentent séparément carbamoyle, alkylcarbamoyle C1-C4, di-alkylcarbamoyle (C1-C4), sulfamoyle, phénylsulfamoyle alkylsulfamoyle C1-C4 ou di-alkylsulfamoyle C1-C4 ; X2, X4 représentent séparément hydrogène, alkyle C1-C4, alcoxy C1-C4, halogène ou nitro; Y1, Y2 représentent séparément hydrogène , alkyle C1-C4, alcoxy C1-C4, halogène ou alkoxycarbonyle C1-C4 ; et Z1, Z2 représentent séparément hydrogène, phényle, naphtyle, benzimidazolonyl, phényle substitué ou naphtyle substitué, les substituants étant au nombre de 1, 2, 3 ou 4 et choisis dans le groupe halogène, nitro, cyano, alcoxycarbonyle C1-C4, carbamoyle, alkylcarbamoyle C1-C4, di-alkylcarbamoyle C1-C4, phénylcarbamoyle, sulfamoyle, phénylsulfamoyle, alkylsulfamoyle C1-C4, di-alkylsulfamoyle C1-C4, acylamino C1-C4, alkyle C1-C4 et alcoxy C1-C4, et les pigments des formules (la) et (Ib) étant différents.
EP16735833.2A 2015-06-25 2016-06-20 Mélanges de pigments naphtol as Withdrawn EP3313941A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102015211828.2A DE102015211828A1 (de) 2015-06-25 2015-06-25 Naphthol AS-Pigment-Mischungen
PCT/EP2016/064200 WO2016207113A1 (fr) 2015-06-25 2016-06-20 Mélanges de pigments naphtol as

Publications (1)

Publication Number Publication Date
EP3313941A1 true EP3313941A1 (fr) 2018-05-02

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
EP16735833.2A Withdrawn EP3313941A1 (fr) 2015-06-25 2016-06-20 Mélanges de pigments naphtol as

Country Status (6)

Country Link
US (1) US10787572B2 (fr)
EP (1) EP3313941A1 (fr)
JP (1) JP2018529785A (fr)
CN (1) CN107735459A (fr)
DE (1) DE102015211828A1 (fr)
WO (1) WO2016207113A1 (fr)

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DE102015211828A1 (de) 2016-12-29
US10787572B2 (en) 2020-09-29
US20180187016A1 (en) 2018-07-05
JP2018529785A (ja) 2018-10-11
CN107735459A (zh) 2018-02-23

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