EP1675913A1 - Preparations de pigments azoiques pour l'heliogravure d'emballages ou la flexographie - Google Patents

Preparations de pigments azoiques pour l'heliogravure d'emballages ou la flexographie

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Publication number
EP1675913A1
EP1675913A1 EP04765816A EP04765816A EP1675913A1 EP 1675913 A1 EP1675913 A1 EP 1675913A1 EP 04765816 A EP04765816 A EP 04765816A EP 04765816 A EP04765816 A EP 04765816A EP 1675913 A1 EP1675913 A1 EP 1675913A1
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EP
European Patent Office
Prior art keywords
azo pigment
weight
pigment preparation
acid
preparation according
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.)
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Application number
EP04765816A
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German (de)
English (en)
Inventor
Heinz Bach
Ulrich Ott
Rainer Winter
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.)
Clariant Produkte Deutschland GmbH
Original Assignee
Clariant Produkte Deutschland GmbH
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Filing date
Publication date
Application filed by Clariant Produkte Deutschland GmbH filed Critical Clariant Produkte Deutschland GmbH
Publication of EP1675913A1 publication Critical patent/EP1675913A1/fr
Withdrawn legal-status Critical Current

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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
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B68/00—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology
    • C09B68/40—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology characterised by the chemical nature of the attached groups
    • C09B68/42—Ionic groups, e.g. free acid
    • C09B68/423—Cationic groups
    • C09B68/4235—Ammonium groups or derivatives thereof
    • 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
    • C09B67/0004—Coated particulate 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
    • 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
    • C09B68/00—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology
    • C09B68/40—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology characterised by the chemical nature of the attached groups
    • C09B68/44—Non-ionic groups, e.g. halogen, OH or SH
    • C09B68/444—Polyether

Definitions

  • Azo pigment preparations for rotogravure and flexographic printing The invention relates to azo pigments which are prepared with a special natural resin derivative with a high acid number and which, when used in concentrates, e.g. for packaging gravure and flexographic printing inks have improved application properties, especially improved rheology.
  • Printing inks, especially gravure and flexographic printing inks are dispersed in varnish and solvents with a high pigment concentration.
  • the concentrate for printing inks thus obtained can be further processed to the finished printing ink.
  • concentrates for printing inks have a pigment content of up to 35%. After dispersing, concentrates are usually stored temporarily in special containers and later made up.
  • EP-A-0 796 900 discloses pigment preparations for water-dilutable printing inks which contain a resin with an acid number of up to 300 mg KOH / g. In the case of azo pigments, however, these preparations still show clear thixotropic behavior.
  • the present invention relates to an azo pigment preparation
  • an azo pigment preparation comprising a) at least one azo pigment, preferably a diaryl yellow pigment, b) a resin based on rosin or modified rosin with an acid number equal to or greater than 320 mgKOH / g, preferably equal to or greater than 330 mg KOH / g, and c) an ammonium salt of a sulfonated yellow diaryl pigment.
  • Preferred azo pigment preparations consist essentially of 50 to 90% by weight, in particular 60 to 80% by weight, of component a), 5 to 45% by weight, in particular 10 to 38% by weight, of component b), and 0.1 to 20% by weight, in particular 2 to 10% by weight, of component c), in each case based on the total weight of the azo pigment preparation.
  • Suitable azo pigments a) are monoazo, disazo, ⁇ -naphthol, naphtol AS, acetoacetylamino-benzimidazolone, acetoacetylamino-quinazolinedione and acetoacetylamino-quinoxalinedione pigments.
  • azo pigments are those with an amine component from the group aniline, 2-nitroaniline, anthranilic acid methyl ester, 2,5-dichloro-aniline, 2-methyl-4-chloroaniline, 2-trifluoromethyl-4-chloroaniline, 2,4,5-trichloroaniline ; 3-amino-4-methyl-benzamide, 4-amino-3-chloro-N'-methylbenzamide, o-toluidine, o-dianisidine, 2,2 ', 5,5'-tetrachlorobenzidine, 2-amino-5-methyl -benzenesulfonic acid and 2-amino-4-chloro-5-methyl-benzenesulfonic acid.
  • azo pigments 4-methyl-2-nitro-phenylamine, 4-chloro-2-nitro-phenylamine, 3,3'-dichlorobiphenyl-4,4'-diamine, SS-dimethyl-biphenyM ⁇ '- diamine, 4-methoxy-2-nitro-phenylamine, 2-ethoxy-4-nitro-phenylamine, 4-amino-2,5-dimethoxy-N-phenylbenzenesulfonamide, 5-amino-isophthalic acid dimethyl ester, anthranilic acid, 2 -Trifluoromethyl-phenylamine, 2-amino-terephthalic acid, dimethyl ester, 1, 2-bis- (2- Amino-phenoxy) -ethane, 2-amino-4-chloro-5-methyl-benzenesulfonic acid, 2-methoxyphenylamine, 4- (4-amino-benzoylamino) -benzamide, 2,4
  • azo pigments are those with a coupling component from the group of acetoacetic arylides of the general formula (I),
  • n is a number from 0 to 3
  • R 1 is a dC -alkyl group, such as methyl or ethyl; a CrC alkoxy group such as methoxy or ethoxy; a trifluoromethyl group; a nitro group; a halogen atom such as fluorine, chlorine or bromine; an NHCOCH 3 group; a S0 3 H group; a SO 2 NR 10 R 11 group in which R 10 and R 11 are identical or different and denote hydrogen or CC alkyl; a COOR 10 group in which R 10 has the meaning given above; or can be a COONR 12 R 13 group in which R 12 and R 13 are independent from each other is hydrogen, C 1 -C 4 alkyl or phenyl, the phenyl ring being substituted by two or three identical or different substituents from the group CrC 4 alkyl, CC alkoxy, trifluoromethyl, nitro, halogen, COOR 10 , where R 10
  • X represents hydrogen, a COOH group or a group of the general formula (III),
  • n and R 1 are as defined above;
  • the bisacetoacetylated diaminophenyls and biphenyls the phenyl or biphenyl ring being unsubstituted or having 1, 2, 3 or 4 identical or different radicals CH 3 , C 2 H 5 , OCH 3 , OC 2 H 5 , NO Z) F, Cl, CF 3 can be substituted;
  • Q 1 , Q 2 and Q 3 may be the same or different and N, NR 2 , CO, N-CO, NR -CO, CO-N, CO-NR 2 , CH , N-CH, NR 2 -CH, CH-N, CH-NR 2 , CH 2 , N-CH 2 , NR 2 -CH 2 , CH 2 -N, CH 2 -NR 2 or S0 2 , where R 2 represents a hydrogen atom; for a C 1 -C 4 -alkyl group, such as methyl or ethyl; or represents a phenyl group which may be unsubstituted or substituted by halogen, CrC 4 alkyl, C 1 -C alkoxy, trifluoromethyl, nitro, cyano, with the proviso that the combination of Q 1 , Q 2 and Q 3 with
  • R 3 is a group CH 3 , COOCH 3 or COOC 2 H 5 ,
  • R 4 is a group CH 3 , SO 3 H or a chlorine atom, and p is a number from 0 to 3, where p> 1 R 4 can be the same or different, into consideration.
  • Particularly preferred azo pigments for the purposes of the present invention are the diaryl yellow pigments.
  • Diaryl yellow pigments are generally understood to mean those of the formula (1)
  • Ar 1 and Ar 2 are the same or different and an unsubstituted or with one to three substituents from the group halogen, such as chlorine, methyl or
  • Methoxy substituted phenyl group and X and Y independently of one another denote H or Cl.
  • Preferred diaryl yellow pigments for the purposes of the present invention are Cl.
  • the rosin is preferably used in the form of commercially available rosins containing resin acids from the group of abietic acid, dehydroabietic acid, laevopimaric acid and palustric acid.
  • resin acids from the group of abietic acid, dehydroabietic acid, laevopimaric acid and palustric acid.
  • the resin acids mentioned can also be used as such.
  • levopimaric acid in particular, which can also be formed from other resin acids via equilibrium reactions, is reacted with a dienophile.
  • Such compounds are known and described in Encyclopedia of Chem. Techn., Vol. 17, 1968, pp. 488-490.
  • resins with a high acid number of at least 320, preferably at least 330, in particular equal to or greater than 340 mg KOH / g resin are used.
  • the resin has the carboxyl group of the original resin acid and the two carboxyl groups or the acid anhydride function of the dienophile.
  • the acid anhydride group can be saponified.
  • component c) are ammonium salts, preferably tetraalkylammonium salts of sulfonated diaryl yellow pigments. Possible diaryl yellow pigments are those mentioned above, PY 12 is particularly preferred. Since component c) should be as sparingly soluble in water as possible, there is expediently only one sulfo group which is either in the radical Ar 1 or in Ar 2 (formula (1)) , As alkyl residues of the ammonium ion, dC 2 o-alkyl residues come into consideration.
  • the ammonium ion preferably contains at least one C 1 -C 20 -alkyl radical, particularly preferably two of them. Particularly preferred ammonium ions are dioctadecyldimethylammonium and dihexadecyldimethylammonium.
  • the particularly preferred component c) is the dioctadecyldimethylammonium sulfonate from Pigment Yellow 12.
  • the azo pigment preparations according to the invention can also contain other auxiliaries (d), such as dispersants, polyester amides, anionic, cationic or nonionic surfactants, such as, for example, alcohol oxyalkylates, antistatic agents, extenders, adjusting agents, Waxes, defoamers, anti-dusting agents, preservatives, wetting agents, antioxidants, UV absorbers, other coloring agents for shading, light stabilizers, or a combination thereof.
  • auxiliaries such as dispersants, polyester amides, anionic, cationic or nonionic surfactants, such as, for example, alcohol oxyalkylates, antistatic agents, extenders, adjusting agents, Waxes, defoamers, anti-dusting agents, preservatives, wetting agents, antioxidants, UV absorbers, other coloring agents for shading, light stabilizers, or a combination thereof.
  • auxiliaries such as dispersants, polyester amides, anionic, cationic or nonionic surfactants, such
  • the other auxiliaries are usually used in amounts of 0 to 40% by weight, preferably 0.01 to 20% by weight, in particular 0.1 to 10% by weight, based on the total weight of the azo pigment preparation.
  • Shading colorants are usually used in amounts of up to 10% by weight, usually 0.01 to 10% by weight, based on the total weight of the azo pigment preparation.
  • the invention also relates to a process for the preparation of the azo pigment preparation according to the invention, characterized in that components a), b), c) and, if appropriate, the further auxiliaries d) are mixed with one another.
  • components c) and d) can be added at one or more points in time during azo pigment production.
  • component a) is a diaryl yellow pigment
  • the procedure is preferably such that an acetoacetylanilide is obtained with a tetrazotized diazonium salt of the corresponding benzidine, in the presence of component c), preferably in an amount of 0.1 to 20% by weight on the total weight of the azo pigment preparation, couples; the resulting pigment suspension is combined with an aqueous alkaline solution of component b) in an amount of 5 to 45% by weight and heated to a temperature between 65 and 150 ° C; the diaryl yellow pigment preparation fails by acidification and, if appropriate, further component d) is incorporated in an amount of 0 to 40% by weight.
  • the diazotization of the diazo component can be carried out by customary methods.
  • Examples of coupling components are acetoacetic anilide,
  • the azo coupling can be carried out in the presence of one or more compounds of component c), which may be added as an aqueous suspension or press cake to either the coupling suspension or the tetrazonium salt of benzidine or to both, or the reaction partners mentioned being combined at the same time.
  • the azo coupling is preferably carried out in an aqueous or aqueous-organic medium, preferably at a pH between 3 and 7, in particular between 4 and 6, and a temperature between 15 and 30 ° C., in particular between 20 and 30 ° C.
  • the pigment suspension is then washed with an aqueous alkaline solution, e.g. in dilute sodium hydroxide solution or potassium hydroxide solution, a resin b), the amount of resin, based on pigment, being 5 to 60% by weight, preferably 10 to 50% by weight.
  • the mixture is then heated to a temperature of 65 to 150 ° C., preferably 80 to 120 ° C., particularly preferably 85 to 100 ° C., for preferably at least 15 minutes, normally 30 minutes to 10 hours.
  • hydrochloric acid, sulfuric acid or acetic acid a pH of preferably 2 to 6, particularly preferably 3 to 5, is set, the azo pigment preparation according to the invention failing.
  • the suspension is filtered, washed free of salt, dried and optionally ground.
  • the suspension of the azo pigment is 1 to 3% by weight of a fatty alcohol alkoxylate, such as e.g. described in EP-B1-0 587 021, added as component d).
  • the azo pigment preparations according to the invention can be used to pigment high-molecular organic materials of natural or synthetic origin, for example plastics, resins, lacquers, paints, electrophotographic toners and developers, electret materials, color filters and inks, printing inks and seeds.
  • High molecular weight organic materials that can be pigmented with the azo pigment preparations according to the invention are, for example Cellulose compounds, such as, for example, cellulose ethers and esters, such as ethyl cellulose, nitrocellulose, cellulose acetates or cellulose butyrates, natural binders, such as, for example, fatty acids, fatty oils, resins and their conversion products, or synthetic resins, such as polycondensates, polyadducts, polymers and copolymers, such as, for example, aminoplasts, in particular Urea and melamine formaldehyde resins, alkyd resins, acrylic resins, phenoplasts and phenolic resins, such as novolaks or resols, urea resins, polyvinyls, such as polyvinyl alcohols, polyvinyl acetals, polyvinyl acetates or polyvinyl ethers, polycarbonates, polyolefins, such as polystyren
  • the azo pigment preparations according to the invention are used in an amount of 0.05 to 30% by weight, preferably 0.1 to 15% by weight.
  • This crude can be used to produce color concentrates in liquid or solid form in concentrations of 5 to 99% by weight, alone or optionally in a mixture with other crudes or finished pigments.
  • the azo pigment preparations according to the invention are also suitable as colorants in electrophotographic toners and developers, such as, for example, one- or two-component powder toners (also called one- or two-component developers), magnetic toners, liquid toners, latex toners, polymerization toners and special toners.
  • Typical toner binders are polymerization, polyaddition and polycondensation resins, such as styrene, styrene-acrylate, styrene-butadiene, acrylate, polyester, phenol-epoxy resins, polysulfones, polyurethanes, individually or in combination, and polyethylene and polypropylene, which also contain other ingredients, such as charge control agents, waxes or flow aids, or can be modified with these additives afterwards.
  • resins such as styrene, styrene-acrylate, styrene-butadiene, acrylate, polyester, phenol-epoxy resins, polysulfones, polyurethanes, individually or in combination, and polyethylene and polypropylene, which also contain other ingredients, such as charge control agents, waxes or flow aids, or can be modified with these additives afterwards.
  • the azo pigment preparations according to the invention are suitable as colorants in powders and powder coatings, in particular in triboelectrically or electrokinetically sprayable powder coatings which are used for the surface coating of objects made of, for example, metal, wood, plastic, glass, ceramic, concrete, textile material, paper or rubber.
  • Epoxy resins, carboxyl- and hydroxyl-containing polyester resins, polyurethane and acrylic resins are typically used as powder coating resins together with conventional hardeners. Also find combinations of resins
  • epoxy resins are often used in combination with carboxyl- and hydroxyl-containing polyester resins.
  • Typical hardener components are, for example, acid anhydrides, imidazoie and dicyandiamide and their derivatives, blocked isocyanates, bisacylurethanes, phenolic and melamine resins, triglycidyl isocyanurates, oxazolines and dicarboxylic acids.
  • the azo pigment preparations according to the invention are suitable as colorants in ink-jet inks on an aqueous and non-aqueous basis, microemulsion inks and in such inks which work according to the hot-melt process.
  • Ink-jet inks generally contain a total of 0.5 to 15% by weight, preferably 1.5 to 8% by weight (calculated on a dry basis) of one or more of the azo pigment preparations according to the invention.
  • Microemulsion inks are based on organic solvents, water and possibly an additional hydrotropic substance (interface mediator).
  • Microemulsion inks generally contain 0.5 to 15% by weight, preferably 1.5 to 8% by weight, of one or more of the azo pigment preparations according to the invention, 5 to 99% by weight of water and 0.5 to 94.5% by weight. -% organic solvent and / or hydrotropic compound.
  • "Solvent based" ink-jet inks preferably contain 0.5 to 15% by weight of one or more of the azo pigment preparations according to the invention, 85 to 99.5% by weight of organic solvent and / or hydrotropic compounds.
  • Hot-melt inks are mostly based on waxes, fatty acids, fatty alcohols or sulfonamides, which are solid at room temperature and become liquid when heated, the preferred melting range being between approx. 60 ° C and approx.
  • Hot-melt ink-jet inks essentially consist, for example, of 20 to 90% by weight of wax and 1 to 10% by weight of one or more of the azo pigment preparations according to the invention. Furthermore, 0 to 20% by weight of an additional polymer (as a "dye dissolver"), 0 to 5% by weight of dispersing aid, 0 to 20% by weight of viscosity modifier, 0 to 20% by weight of plasticizer, 0 to 10% by weight % Stickiness additive, 0 to 10% by weight transparency stabilizer (prevents, for example, crystallization of the waxes) and 0 to 2% by weight antioxidant.
  • an additional polymer as a "dye dissolver”
  • dispersing aid 0 to 20% by weight of viscosity modifier
  • plasticizer 0 to 20% by weight of plasticizer
  • Stickiness additive 0 to 10% by weight
  • transparency stabilizer prevents, for example, crystallization of the waxes
  • the azo pigment preparations according to the invention are also used as colorants for color filters, both for additive and for subtractive color production, and as colorants for electronic inks (“electronic inks” or “e-inks”) or “electronic paper” (“e- paper ").
  • the pigment preparations according to the invention can be easily dispersed in varnishes customary for gravure printing inks, for example for gravure printing and flexographic printing, and produce printing inks with high gloss and particularly good rheological properties, namely lower thixotropy.
  • One object of the present invention is therefore in particular the use of the azo pigment preparations described for the production of printing inks, in particular gravure printing inks and flexographic printing inks.
  • percentages are percentages by weight unless otherwise specified.
  • a dome component suspension with a pH of 5.6 prepared by dissolving 37.6 parts of acetoacetic acid-m-xylidide with 29.4 parts of 33% sodium hydroxide solution in 500 parts of water and subsequent precipitation with 20 parts of 80% acetic acid, 4 parts of a fatty alcohol alkoxylate according to EP-A-0 587 021, Example 1 and 3.2 parts of dioctadecyldimethylammonium sulfonate from PY12 (component c) are added. The suspension is then coupled in two hours at a temperature of 20 to 25 ° C.
  • aqueous 3,3'-dichlorobenzidine tetrazo solution prepared by bisdiazotizing 23 parts of 3, 3'-dichlorobenzidine in dilute HCl and sodium nitrite.
  • the pH of the pigment suspension is adjusted to about 9 using sodium hydroxide solution, and a resin solution consisting of 20O parts of water, 22.2 parts of 33% NaOH and 16.9 parts of one is added
  • Example 2 The procedure is as in Example 1, but with the difference that a fumaric acid-rosin adduct with an acid number of 300 is used as the resin. 85 g of a diaryl yellow pigment preparation containing PY 13 are obtained. Comparative Example b The procedure is as in Example 1, but with the difference that a maleic acid-rosin adduct with an acid number of 150 is used as the resin. 84 g of a diaryl yellow pigment preparation containing PY 13 are obtained.
  • Example 2 To a dome component suspension with a pH of 5.0, prepared by indirect precipitation from 69.5 parts of N- (4-chloro-2,5-dimethoxyphenyl) -3-hydroxy-2-naphthalene carboxamide dissolved in 81 parts 33% sodium hydroxide solution in 400 parts of water and subsequent precipitation in 400 parts of water, 81 parts of 31% hydrochloric acid, 10.2 parts of 80% acetic acid, 3 parts of a fatty alcohol alkoxylate according to EP-A-0 587 021, Example 1. The suspension is then coupled in one hour at a temperature of 40 ° C.
  • Example 1 5.5 parts of a commercially available fatty alcohol alkoxylate according to EP-A-0 587 021, Example 1 are then added to the suspension. At 65 ° C. (cooling with ice), the suspension is adjusted to pH 5 with hydrochloric acid, filtered, washed until salt-free, in the press cake 1.8 parts of dioctadecyldimethylammonium sulfonate from PY12 (component c), kneaded at 80 ° C. and ground on a pin mill. 134 g of a pigment preparation containing P.R. 146th
  • Example 2 The procedure is as in Example 2, but with the difference that a fumaric acid-rosin adduct with an acid number of 300 is used as the resin. 136 g of a pigment preparation containing PR 146 are obtained. Comparative Example 2b The procedure is as in Example 2, but with the difference that a maleic acid-rosin adduct with an acid number of 150 is used as the resin. 136 g of a pigment preparation containing PR 146 are obtained.
  • Example 3 0.3 part of a nonionic surfactant (nonylphenol oxyethylate), 19 parts of 33% sodium hydroxide solution, 19 parts of 80% acetic acid are stirred into 600 parts of water and 64.7 parts of acetoacetic acid anilide are introduced at 10 ° C. The suspension is then coupled in two hours at a temperature of 20 to 25 ° C and a pH range of 5.6 to 4 with an approx. 10% aqueous 3,3'-dichlorobenzidine tetrazo solution (prepared by bisdiazotizing 23 parts 3 , 3'-dichlorobenzidine in dilute HCl and sodium nitrite).
  • a nonionic surfactant nonylphenol oxyethylate
  • the pH of the pigment suspension is adjusted to about 9 using sodium hydroxide solution and 0.4 parts of a fatty alcohol alkoxylate according to EP-A-0 587 021, Example 1, are added to it, with a resin solution consisting of 82 parts of water, 6.1 parts 33% NaOH and 8.17 parts of a maleic rosin adduct with the acid number 360.
  • the temperature of the suspension is raised to 95 ° C. and held for 3 hours. Then, the suspension is mixed with 1.2 parts of dioctadecyldimethylammonium sulfonate from P.Y.12 (component c). At 65 ° C
  • Example 3 The procedure is as in Example 3, but with the difference that a fumaric acid-rosin adduct with an acid number of 300 is used as the resin. 65 g of a diaryl yellow pigment preparation containing P.Y. 12th
  • Example 4 To a dome component suspension with a pH of 5.6, prepared by indirect precipitation from 49.9 parts of acetoacetic acid (2,5-dimethoxy-4-chloroanilide) dissolved in 25 parts of 33% sodium hydroxide solution in 200 parts Water and subsequent precipitation in 400 parts of water, 23.4 parts of 80% acetic acid, 5 parts of a nonionic surfactant (nonylphenol oxyethylate) are added. The suspension is then coupled in one hour at a temperature of 20 to 25 ° C.
  • acetoacetic acid 2,5-dimethoxy-4-chloroanilide
  • the pH of the pigment suspension is adjusted to about 9 using sodium hydroxide solution and a resin solution consisting of 150 parts of water, 8 parts of NaOH and 9.7 parts of a maleic acid-rosin adduct with an acid number of 360 is added.
  • the temperature of the suspension is raised 95 ° C increased and held for 0.5 hours.
  • the suspension is then mixed with 5 parts
  • Example 4 The procedure is as in Example 4, but with the difference that a maleic acid-rosin adduct with an acid number of 300 is used as the resin. 91.5 g of a diaryl yellow pigment preparation containing PY 83 are obtained. Comparative Example 4c The procedure is as in Example 4, but with the difference that a maleic acid-rosin adduct with an acid number of 150 is used as the resin. 92 g of a diaryl yellow pigment preparation containing PY 83 are obtained.
  • Example 5 A dome component suspension with a pH of 5.5, prepared by dissolving 39.0 parts of acetoacetic acid-o-anisidide with 48.3 parts of 33% sodium hydroxide solution in 200 parts of water and subsequent precipitation with 33 parts of 80% acetic acid , is in two hours at a temperature of 18 to 20 ° and a pH range 5.5 to 4 with an approximately 10% aqueous 2-diazonium chloride-5-nitroanisole solution (prepared by diazotization of 30.6 parts 5 -Nitro-2-amino-anisole in dilute HCl and sodium nitrite) coupled.
  • aqueous 2-diazonium chloride-5-nitroanisole solution prepared by diazotization of 30.6 parts 5 -Nitro-2-amino-anisole in dilute HCl and sodium nitrite
  • the pH of the pigment suspension is adjusted to about 9, mixed with a resin solution consisting of 235 parts of water, 17.6 parts of 33% NaOH, 11 parts of a maleic acid-rosin adduct with an acid number of 360 and with 2 parts of one commercially available fatty alcohol alkoxylate with cloud point approx. 40 ° C.
  • the temperature of the suspension is raised to 95 ° C and held for 0.5 hours.
  • the suspension is adjusted to pH 5 with hydrochloric acid, with 5 parts of dioctadecyldimethylammonium sulfonate from P.Y.12
  • Example 5 The procedure is as in Example 5, but with the difference that a fumaric acid-rosin adduct with an acid number of 300 is used as the resin. 85 g of a diaryl yellow pigment preparation containing PY 74 are obtained. applications
  • NC alcohol gravure varnish of the following composition:
  • Solvent mixture with the following composition: 98.0% ethanol (99.9%) 2.0% ethyl acetate (99.9%) 100.0%
  • the dispersing concentrates are tempered at 23 ° C. With help of a
  • the thixotropy value ⁇ A is determined by the difference of the areas between the up curve of the ⁇ axis and the down curve of the ⁇ axis. This calculation is integrated in the measurement process.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Dispersion Chemistry (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)

Abstract

Préparation de pigments azoïques qui contient (a) au moins un pigment azoïque, (b) une résine à base de colophane ou de colophane modifiée ayant un indice d'acidité égal ou supérieur à 320 mgKOH/g, et (c) un sel d'ammonium d'un pigment jaune diaryle sulfoné.
EP04765816A 2003-10-16 2004-10-05 Preparations de pigments azoiques pour l'heliogravure d'emballages ou la flexographie Withdrawn EP1675913A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10348106A DE10348106A1 (de) 2003-10-16 2003-10-16 Azopigmentpräparationen für den Verpackungstief- und Flexodruck
PCT/EP2004/011102 WO2005037929A1 (fr) 2003-10-16 2004-10-05 Preparations de pigments azoiques pour l'heliogravure d'emballages ou la flexographie

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EP (1) EP1675913A1 (fr)
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WO (1) WO2005037929A1 (fr)

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JP5350827B2 (ja) * 2009-02-09 2013-11-27 富士フイルム株式会社 インク組成物、及び、インクジェット記録方法
US8273166B2 (en) * 2011-01-18 2012-09-25 Xerox Corporation Phase change ink compositions and colorants for use in the same
JP2020055970A (ja) * 2018-10-03 2020-04-09 Ｄｉｃグラフィックス株式会社 ラミネート用印刷インキ
JP2021080402A (ja) 2019-11-21 2021-05-27 Ｄｉｃグラフィックス株式会社 リキッド印刷インキ、及び積層体
CN115216750A (zh) * 2022-07-28 2022-10-21 河南华福包装科技有限公司 一种氧化硅高阻隔膜、温变高阻隔包装材料及其制备工艺

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JP2007508428A (ja) 2007-04-05
WO2005037929A1 (fr) 2005-04-28
US7318863B2 (en) 2008-01-15
CN100381503C (zh) 2008-04-16
US20070204762A1 (en) 2007-09-06
CN1867639A (zh) 2006-11-22
DE10348106A1 (de) 2005-05-19

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