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
  • C09B67/006—Preparation of organic pigments
• • 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
  • G03F1/00—Originals for photomechanical production of textured or patterned surfaces, e.g., masks, photo-masks, reticles; Mask blanks or pellicles therefor; Containers specially adapted therefor; Preparation thereof
  • G03F1/54—Absorbers, e.g. of opaque materials
  • G03F1/56—Organic absorbers, e.g. of photo-resists
• • 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
  • C09B29/00—Monoazo dyes prepared by diazotising and coupling
  • C09B29/32—Monoazo dyes prepared by diazotising and coupling from coupling components containing a reactive methylene group
  • C09B29/33—Aceto- or benzoylacetylarylides
  • C09B29/335—Aceto- or benzoylacetylarylides free of acid groups
  • C09B29/338—Heterocyclic arylides, e.g. acetoacetylaminobenzimidazolone
• • 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
  • C09B33/00—Disazo and polyazo dyes of the types A->K<-B, A->B->K<-C, or the like, prepared by diazotising and coupling
  • C09B33/02—Disazo dyes
  • C09B33/153—Disazo dyes in which the coupling component is a bis-(aceto-acetyl amide) or a bis-(benzoyl-acetylamide)
• • 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
  • C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
  • C09B35/02—Disazo dyes
  • C09B35/021—Disazo dyes characterised by two coupling components of the same type
  • C09B35/035—Disazo dyes characterised by two coupling components of the same type in which the coupling component containing an activated methylene group
• • 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
  • C09B67/0077—Preparations with possibly reduced vat, sulfur or indigo 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
  • G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
  • G03F7/105—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images

Definitions

• the present invention relates to pigment dispersions, a process for their preparation and the pigment dispersions obtainable by this process and their use for pigmenting high molecular weight material.
• the pigments should have pure, strong and brilliant shades that make it possible to open up a large color space. Furthermore, they should not only be able to be used as a single pigment, but also as a combination element in, for example, trichromatic pigments. In terms of application technology, it proves to be advantageous to apply the pigment as a dispersion, since complex mixing and grinding operations, which represent an additional hygienic burden, can be avoided. In addition, dispersions provide better reproducibility of the pigmentation process because the pigment particles are more homogeneously distributed than in the powder form. For economic reasons, it is particularly desirable to use concentrated, stable dispersions which require little space during transport or storage and at the same time have good stability.
• compositions of polymers and latent pigments from EP-A 654 711 are known, as are chemical, thermal or photolytic methods with which
• Pigment particles can be generated by known methods, in previously structured layers consisting of polymers and soluble pigment precursors.
• polymer is synonymous with polymer and / or
• the object of the present invention was therefore to provide pigment dispersions which have a high stability and a good transparency and a process for their preparation.
• the present invention accordingly relates to a method for producing
• Pigment dispersions of a pigment, a polymer and a solvent by a1) a mixture A, containing a latent pigment and a polymer, thermally, chemically or photolytically treated and b) then mixed with a solvent, or a2) a mixture B, containing a Latent pigment, a polymer and a
• Solvents thermally, chemically or photolytically treated.
• the weight ratio of latent pigment to polymer of mixtures A and B is selected in the range from 1: 1 to 1:20, preferably in the range from 1: 1, 5 to 1:10 and particularly preferably in the range from 1: 1, 5 to 15.
• the pigments are produced from the soluble pigment precursors, the latent pigments, by thermal, chemical or photolytic treatment, which can be carried out in analogy to EP-A 654 711 or EP-A-742255.
• Mixture A or B is usually treated thermally.
• the mixture is heated in the temperature range from 100 to 200 ° C. for one minute to 36 hours, particularly preferably in the temperature range from 120 to 150 ° C. for 10 minutes to 24 hours.
• the thermal treatment is carried out under pressure.
• this is selected in the range from 70 kPa to 10 MPa, preferably from 90 kPa to 5 MPa, with atmospheric pressure being particularly preferred.
• Mixtures A and B can generally be prepared for one minute to 36 hours, preferably for 10 minutes to 24 hours, by generally known methods of mixing, such as by stirring, kneading or swirling.
• the mixing and the thermal treatment of mixture A is carried out in the extruder.
• the process steps in the extruder can be carried out continuously or batchwise.
• any type of extruder can be used, for example two-screw extruders or kneading extruders, with two-screw extruders rotating with one another being particularly preferred.
• the operation with an extruder is generally known and is described, for example, in "The Canadian Journal of Chemical Engineering", 71, June 1993 and US 3,637,545.
• a further embodiment of the process according to the invention therefore relates to production in the extruder by thermally treating mixture A in an extruder.
• Mixtures A or B are preferably homogeneous mixtures.
• Mixture B is particularly preferably a solution, and very particularly preferably a homogeneous solution, in the components are evenly distributed.
• the word homogeneous here limits to "macroscopically uniform” and is in this sense the opposite of heterogeneous; since homogeneous is not synonymous with “pure, unmixed", mixtures can also be homogeneous, such as powder, saline, wine, milk chocolate (Römpp, 1997, p. 1795).
• mixture A can be prepared by mixing the latent pigment and the polymer with a solvent and then removing the solvent by generally known methods.
• solvents are used in which the latent pigment and / or the polymer, particularly preferably latent pigment and polymer, are dissolved.
• the solvent-containing mixtures A or B of latent pigment and polymer are prepared by stirring, preferably intensive stirring.
• the mixtures comprising latent pigment, polymer and solvent are prepared by separately preparing two mixtures, one each from latent pigment and solvent and one from polymer and solvent, which are generally preferred for one minute to 24 hours during 10 minutes to 12 hours. If desired, it is also possible to first mix a latent pigment and polymer and then add a solvent to this mixture.
• solvent means non-water-containing organic and / or water-containing solvents, which may contain organic solvents, and / or solvent mixtures thereof.
• polar, aprotic solvents such as aliphatic CrC 4 alcohols such as methanol, ethanol, 1- or 2-propanol, 1- or 2-isopropanol, n-butanol, sec-butanol, tert.
• -Butanol also polyols, cellosolves and carbitols such as ethylene glycol, diethylene glycol, triethylene glycol, glycerol, propylene glycol, diacetone alcohols such as 4-hydroxy-4-methyl-2-pentanone or ether alcohols such as bis (2-hydroxyethyl) ether, bis (2 hydroxyproplyl ether or bis (2-hydroxybutyl) ether, ethylene glycol monomethyl or monoethyl ether, propylene glycol methyl ether, dipropylene glycol methyl ether, tripropylene glycol methyl ether, ethylene glycol phenyl ether, ethylene glycol methyl ether, propylene glycol phenyl ether, diethylene glycol monomethyl or monoethyl ether, diethylene glycol monobutyl ether, triethylene glycol monomethyl or monoethyl ether, further ethers such as dioxane, dimethoxyethane or tetra
• the solvent is usually used in 50 to 99.99% by weight, preferably 80 to 99.99% by weight, based on the total weight of latent pigment and polymer.
• the thermal treatment of latent pigment and polymer can be carried out with or without a solvent.
• mixture B can also be concentrated on, preferably up to 20% by weight of the total mass of latent pigment and polymer.
• the solvent is usually removed by generally known methods such as distillation, preferably under reduced pressure.
• mixture A which contains no solvent, can be dried before the thermal treatment, preferably in the temperature range from 40 to 150 ° C. for 1 hour to 24 hours and particularly preferably in the temperature range from 40 to 80 ° C. for 1 hour to 12 hours.
• the thermally, chemically or photolytically treated mixture A is provided with a non-water-containing organic and / or water-containing solvent.
• the thermally, chemically or photolytically treated mixture B can also be mixed with a solvent, or a solvent change can be carried out.
• the solvent can be changed by generally known methods, such as by distilling off the solvent, decanting or filtering and then adding the desired solvent.
• the solvent is mixed after the thermal, chemical or photolytic treatment by the customary methods of mixing, in particular by stirring the components.
• a dispersion containing pigment, polymer and solvent can also be prepared directly from mixture B, preferably a homogeneous mixture B and particularly preferably a solution containing latent pigment, polymer and solvent, during the thermal treatment.
• fine pigment dispersion is prepared by mixing a solution of latent pigment with a solution of polymer, concentrating the reaction mixture obtained by distilling off the solvent, particularly preferably concentrating to dryness, and heating the resulting concentrate by thermal treatment Mixture containing pigment and polymer is produced, which is dispersed in water-containing and / or non-water-containing organic solvents.
• the present invention therefore also relates to a process for the production of pigment dispersions from a pigment, a polymer and a solvent by d) a mixture comprising a latent pigment, a polymer and a
• the present invention relates to a process for the preparation of pigment dispersions from a pigment and a polymer by thermal, chemical or photolytic treatment of a solution C containing a latent pigment, a polymer and a solvent.
• a further preferred embodiment of the present invention relates to a process for the preparation of pigment dispersions from a pigment, a polymer and a solvent by g1) a solution C containing a latent pigment, a polymer and a solvent, and g2) subsequently from the so solution obtained, the solvent is removed, and g3) thereafter the solvent-free mixture is treated thermally, chemically or photolytically, and g4) the solvent is then added to the treated mixture.
• pigment dispersions are prepared from a pigment, a polymer and a solvent by preparing d1) a mixture B containing a latent pigment, a polymer and a solvent, and d2) subsequently from the mixture thus obtained Partly removed solvent, and d3) then treated the mixture thus obtained thermally, chemically or photolytically.
• the process according to the invention can be used to produce non-aqueous and aqueous pigment dispersions.
• the present invention relates to the preparation of non-water-containing dispersions by treating e1) a mixture A comprising a latent pigment and a polymer, thermally, chemically or photolytically and e2) thereafter with a non- added water-containing solvent, or e3) a mixture B containing a latent pigment, a polymer and a non-water-containing solvent, thermally, chemically or photolytically treated.
• Non-aqueous solvents are organic solvents.
• the present invention also relates to the preparation of water-containing pigment dispersions by treating f1) a mixture A comprising a latent pigment and a polymer, thermally, chemically or photolytically and f2) then adding a water-containing solvent , or f3) a mixture B, containing a latent pigment, a polymer and a water-containing solvent, thermally, chemically or photolytically treated.
• Aqueous solvents stand for water, which can additionally contain organic solvents and / or bases.
• the thermally, chemically or photolytically treated mixture is mixed with a water-containing solution, preferably a water-containing solution containing a base.
• the thermally, chemically or photolytically treated mixture can be mixed with a water-miscible organic solvent such as dioxane or tetrahydrofuran, which preferably dissolves the polymer, before mixing with a water-containing solution.
• a water-miscible organic solvent such as dioxane or tetrahydrofuran, which preferably dissolves the polymer, before mixing with a water-containing solution.
• the water-containing pigment dispersions are adjusted to a pH> 7, particularly preferably to a pH> 8.
• the pH can be adjusted by mixing the water-containing mixture containing pigment, polymer and water with a base, or by mixing the thermally, chemically or photolytically treated mixture with a water-containing solution containing a base.
• the bases contained in the water-containing solutions are organic or inorganic bases.
• the organic bases used are preferably hydroxides of organic cations such as trimethylammonium or triethylammonium or amines such as mono-, di- or tri-methylamine, mono-, di- or tri-ethylamine or
• Lithium, potassium or sodium hydroxide are preferably used as inorganic bases. Dimethylaminoethanol or morpholine are particularly preferred.
• a water-containing pigment dispersion is prepared by a) mixing the thermally, chemically or photolytically treated mixture with an organic solvent, in particular with a water-miscible organic solvent, and b) subsequently by adding a water-containing one Solution containing a base, especially an organic base, adjusts the pH to> 7.
• the organic solvent is removed.
• the solvent is removed by distillation, which is preferably carried out under reduced pressure.
• the pigment dispersions according to the invention may optionally have a residual proportion of latent pigment, based on pigment, of at most 10% by weight, but preferably less than 5% by weight and very particularly preferably less than 1% by weight.
• the pigment dispersions according to the invention have a pigment concentration in the range from 0.01 to 10% by weight, preferably from 0.1 to 5% by weight, based on the total weight of the pigment dispersion.
• the fine pigment dispersions produced by the process according to the invention preferably have an average particle size distribution of 0.015-0.5 micrometers, particularly preferably 0.03-0.3 micrometers and very particularly preferably from 0.05-0.2 microns.
• the particle size distribution was determined using the Joyce-Loebl disc centrifugation method.
• the dispersion according to the invention can additionally contain additives, such as surface-active compounds, which have a preferred spatial orientation in solvents.
• additives such as surface-active compounds, which have a preferred spatial orientation in solvents.
• the water-based pigment dispersions are large molecules consisting of a hydrophilic head and a hydrophobic tail, such as Fluorad FC-170, a non-ionic fluorine-containing surfactant, from 3 M Inc. (or like OLOA TM 1200 from Chevron Corp., Richfield, CA, Amoco TM 9250, from Amoco Chemical Co., Naperville, IL).
• the dispersions obtained preferably have ⁇ 20% by weight, more preferably from ⁇ 10% by weight and very particularly preferably ⁇ 5% by weight of additives and, if desired, can also contain further cosolvents, such as, for example, cyclohexanone, cyclopentanone, N, N '-Dimethylformamide or dimethyl sulfoxide.
• Polymers consisting of a hydrophilic and hydrophobic part are preferably used as polymers for water-containing pigment dispersions.
• the former part can be ionizable and form salts or be non-ionizable.
• the polymers are preferably random, block or graft polymers.
• the hydrophilic part of the polymers is preferably composed, for example, of monomers which, in addition to functional groups such as, for example, alcohol, carboxylic acid, carboxamide, carboxylic ester or sulfonic acid groups, sulfate, cyanate or carboxylic anhydride, or ether groups such as ethylene or Propylene oxide groups and in addition a polymerizable vinyl or vinylene residue such as an acrylic, or methyl-acrylic, crotyl, sulfoethylmethylacryl, sulfopropylmethylacryl, vinylnaphthyl, vinylphenyl, vinyltolyl residue and an itaconyl residue such as, for example, itaconyl monoester, maleic acid or a maleinyl residue such as Examples include maleic acid monoesters, a fumaryl radical such as, for example, fumaryl monoesters and in particular vinylbenzoic acid.
• functional groups such as, for example, alcohol, carboxylic acid, car
• the monoesters are preferably monoesters of itaconyl, maleic or fumaric acid.
• Monomers are preferred which have carboxyl, carboxylic anhydride, sulfonate or sulfate groups as functional groups.
• Carboxyl or carboxylic anhydride groups such as vinylbenzoic acid or maleic anhydride are particularly preferred.
• the hydrophobic part of the polymers are preferably selected from the group of the apolar monomers consisting of styrene, styrene derivatives, such as C t ⁇ alkyl substituted styrene, and vinyl chloride, vinylnaphthalene, Vinylnaphthalinderivaten as -C 4 alkyl-substituted vinyl naphthalene, vinyl toluene, ⁇ , m, p or m, p vinyl toluene and aliphatic, C 12 -C 18 alkenes.
• the preferred hydrophobic non-polar monomers are, for example, styrene, vinyl toluene and octadecene.
• copolymers with a narrow molar mass distribution in the range of 1-2 Mw / Mn (where Mw means mean weight and Mn means mean number).
• the molar mass (number average) of the copolymers is preferably ⁇ 100000 g / mol.
• Copolymers consisting, for example, of styrene, vinyltoluene and vinylbenzoic acid monomers preferably have a molar mass of 10000-30000 g / mol, particularly preferably 15000-20000 g / mol and very particularly preferably 10000-15000 g / mol.
• a further preferred embodiment of the invention relates to copolymers which are produced, for example, from styrene and maleic anhydride monomers, preferably have a molar mass of 500-5000 g / mol, particularly preferably 1000-3000 g / mol and very particularly preferably 500- 1500 g / mol.
• Acrylate, methacrylate, styrene and vinyl polymers are usually used for non-aqueous pigment dispersions.
• polyvinyl butyrate are used for ethanolic pigment dispersions and methyl methacrylate for dispersions with methyl ethyl ketone as solvent or copolymers of methyl methacrylate and butyl acrylate for pigment dispersion with chloroform as solvent.
• Preferred polymers for water-containing pigment dispersion are composed, for example, of polymers containing carboxyl groups, such as, for example, styrene, vinyltoluene and vinylbenzoic acid or vinylbenzoic acid and nonpolar monomers, and of styrene and maleic anhydride or of copolymers of long-chain alkenes (C 12 -C 18 ) with maleic anhydride such as, for example, styrene -Maleic anhydride, styrene-vinyltoluene-vinylbenzoic acid or octadecene-maleic anhydride together.
• polymers containing carboxyl groups such as, for example, styrene, vinyltoluene and vinylbenzoic acid or vinylbenzoic acid and nonpolar monomers
• a preferred embodiment of the process according to the invention relates to the production of water-containing basic pigment dispersions from a latent pigment with a solution of a copolymer containing vinylbenzoic acid and a non-polar monomer or with a solution containing a carboxyl group-containing polymer.
• the polymers for aqueous or non-aqueous pigment dispersions are commercially available, for example from the company, Scientific Polymer Products Inc., or can be prepared by known methods, for example as described in US Pat. No. 4,597,764 or 4,508,880, or for example for the production of carboxyl-containing products
• Copolymers given in Example 1 can be prepared by radical polymerization of the monomers in the presence of a radical initiator such as 4,4'-azobis (4-cyanopentanoic acid) and a radical transfer agent such as dodecyl mercaptan.
• the monomers and polymerization or copolymerization aids such as free radical initiators or free radical transfer agents and solvents, are commercially available products and can be obtained, for example, from Fluka.
• Latent pigments are understood to mean soluble pigment precursors as described, for example, in US Pat. No. 5,616,725 and 5,561, 232.
• Isoindoline, isoindolinone, perylene, and phthalocyanine series which is about a
• Heteroatoms are selected from the group consisting of N, O or S and form part of the radical A, and
• R 5 and R 6 are substituted d-Ce alkylene or C 2 -C 5 alkenylene, or R 1 and R 2 independently of one another are hydrogen, CrC ⁇ -al yl, CrC 6 alkoxy,
• R 3 and R independently of one another are hydrogen, dC 4 alkyl or a group
• R 5 and R 6 are independently hydrogen, CC 24 alkyl, through O, S or, with
• R 7 , R 8 and R 9 are independently hydrogen, CrC 24 alkyl or C 3 -C 24 alkenyl
• R 82 is hydrogen, -CC 6 alkyl or a group of the formula
• R 84 is hydrogen or dC 6 -AII ⁇ yl
• R 85 is hydrogen, d-C ⁇ -alkyl, unsubstituted or substituted by C r C 6 -alkyl phenyl, or
• G 1 is unsubstituted or singly or multiply with CC 12 alkyl, C r C ⁇ 2 alkoxy, dC 12 alkylthio or C -C 24 dialkylamino is substituted p, qC 2 -C 12 alkylene, where p and q are different position numbers,
• G 2 represents a heteroatom selected from the group consisting of N, O or S, and wherein, i if G 2 is O or S, the number 0 and, if G 2 is N, the number 1, and
• R 10 and Rn independently of one another unsubstituted or singly or multiply with dC 12 alkoxy, dC ⁇ alkylthio, C 2 -C 2 dialkylamino, C 6 -C ⁇ aryloxy, C 6 -C 12 arylthio, C 7 -C 24 alkylarylamino or C 12 - C 24 diarylamino substituted dC 12 alkyl or [- (p'.q'-Ca-C ⁇ alkyleneJ-R ⁇ -J ü -dC ⁇ alkyl, wherein ii is a number from 1 to 1000, p 'and q' are different Position numbers are
• R 12 independently of the others, denotes a heteroatom O, S or CrC 12 alkyl-substituted N, and C 2 -C 12 alkylene in the repeating units [C 2 -C 1 alkylene-R 12 ] can be identical or different, and
• Alkyl or alkylene can be straight-chain, branched, monocyclic or polycyclic.
• any substituents are CC alkylene, it is a straight-chain or branched alkylene such as, for example, methylene, dimethylene, trimethylene, 1-methyl-methylene, 1, 1-dimethyl-methylene, 1, 1-dimethyl-dimethylene, 1- Ethyl dimethylene, 1-ethyl-1-methyl dimethylene or tetramethylene.
• XCC 6 is alkylene, it is a straight-chain or branched alkylene such as, for example, methylene, dimethylene, trimethylene, 1-methyl-methylene, 1, 1-dimethyl-methylene, 1-ethyl-dimethylene, 1-ethyl-1 -methyl-dimethylene, tetramethylene, 1, 1-dimethyl-ethylene, 1, 1-dimethyl-propylene, 2,2-dimethyl-propylene, 1-ethyl-propylene, 2-ethyl-propylene, 2-methyl-butylene, pentamethylene, hexamethylene , 2,2-dimethylbutylene, 3,3-dimethylbutylene, 2,2-dimethylbutylene, or 1-ethylbutylene, 2-ethylbutylene.
• alkylene such as, for example, methylene, dimethylene, trimethylene, 1-methyl-methylene, 1, 1-dimethyl-methylene, 1-ethyl-dimethylene, 1-ethyl-1 -methyl
• X as C 2 -C 5 alkenylene means straight-chain or branched alkenylene such as, for example, vinyl, allyl, methallyl, 1-methyl-2-butenyl or 2-butenyl.
• any substituents p, qC 2 -C 4 alkylene are, it is, for example, 1, 2-ethylene, 1, 2-propylene, 1, 3-propylene, 1, 2-butylene, 1, 3-butylene, 2,3-butylene, 1,4-butylene or 2-methyl-1,2-propylene.
• any substituents p.q-d-C ⁇ alkenylene mean, it is, for example, an isomer of pentylene, hexylene, octylene, decylene or dodecylene.
• any substituents are dd-alkyl, it is, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl or tert-butyl, cyclobutyl.
• d-C ⁇ -Alkyl can additionally be n-pentyl, 2-pentyl, 3-pentyl, 2,2-dimethylpropyl, cyclopentyl, cyclohexyl, n-hexyl or dimethylbutyl, and in addition d-dralkyl means, for example, n-octyl, 1, 1 , 3,3-tetramethylbutyl, 2-ethylhexyl, nonyl, trimethylcyclohexyl, decyl, menthyl, thujyl, bornyl, 1-adamantyl, 2-adamantyl or dodecyl, and dC 24 -alkyl, furthermore tetradecyl, hexadecyl, octadecyl, eicosyl, heneicosyl , Docosyl or Tetracosyl mean.
• C 2 -C 2 alkyl is mono- or polyunsaturated, it is C 2 -C 12 alkenyl, C 2 -C 12 alkynyl, C 2 -C 12 alkapolyenyl or C 2 -C 2 alcapolyvinyl , in which two or more double bonds may optionally be isolated or conjugated such as vinyl, allyl, 2-propen-2-yl, 2-buten-1-yl, 3-buten-1-yl, 1, 3-butadien-2 -yl, 2-Cyclobuten-1 -yl, 2-penten-1-yl, 3-penten-1-yl, 2-methyl-1-buten-3-yl, 2-methyl-3-buten-2-yl , 3-methyl-2-buten-1-yl, 1,4-pentadien-3-yl, 2-cyclopenten-1-yl, 2-cyclohexen-1-yl, 3-cyclohexen-1-yl, 2,4 - Cyclohexadien-1-yl,
• C 3 -C 24 alkenyl is C 3 -C 24 alkyl which is mono- or polyunsaturated, it being possible for two or more double bonds to be isolated or conjugated, for example allyl, 2-propen-2-yl, 2- Buten-1-yl, 3-buten-1-yl, 1, 3-butadien-2-yl, 2-penten-1-yl, 3-penten-2-yl, 2-methyl-1-buten-3- yl, 2-methyl-3-buten-2-yl, 3-methyl-2-buten-1-yl, 1, 4-pentadien-3-yl, or the various isomers of hexenyl, octenyl, nonenyl, decenyl, dodecenyl , Tetradecenyl, Hexadecenyl, Octadecenyl, Eicosenyl, Heneicosenyl, Docosenyl, Tetra- cosenyl, Hexadienyl,
• Ci 2 -C 18 alkenes means for example Do-, Tri-, Tetra-, Penta-, Hexa-, Hepta- or Octadecen.
• C 4 -C 12 cycloalkyl is, for example, a monocyclic cycloalkyl such as cyclobutyl, cyclopentyl, cyclohexyl, trimethylcyclohexyl or menthyl, or a polycyclic cycloalkyl such as thujyl, bornyl, 1-adamantyl or 2-adamantyl.
• C 4 -C 12 cycloalkenyl is C -C 12 cycloalkyl which is mono- or polyunsaturated, it being possible for two or more double bonds to be isolated or conjugated, for example 2-cyclobuten-1-yl, 2-cyclopenten-1 -yl, 2-cyclohexen-1-yl, 3-cyclohexen-1-yl, 2,4-cyclohexadien-1-yl, 1-p-menthen-8-yl, 4 (10) -Thujen-10-yl, 2-norbornen-1-yl, 2,5-norbornenadien-1-yl or 7,7-dimethyl-2,4-norcaradien-3-yl.
• C 3 -C 24 alkynyl is C 3 - C 24 alkyl or C 3 -C 24 alkenyl which is doubly unsaturated one or more times, wherein the triple bonds may optionally be isolated or conjugated among themselves or with double bonds, for example 1-propin-3-yl, 1-butyn-4-yl, 1-pentyn-5-yl, 2-methyl-3-butyn-2-yl, 1, 4-pentadyn-3-yl, 1, 3- Pentadiin-5-yl, 1-hexin-6-yl, cis-3-methyl-2-penten-4-in-1-yl, trans-3-methyl-2-penten-4-in-1-yl, 1, 3-hexadiin-5-yl, 1-octin-8-yl, 1-nonin-9-yl, 1-decin-10-yl or 1-tetracosin-24-yl.
• d-C ⁇ -alkoxy means methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, tert-butoxy, n-amyloxy, tert-amyloxy or n-hexyloxy.
• dC 12 alkoxy is -0-CC 12 alkyl, preferably -OC C 4 alkyl.
• C 6 -C 12 aryloxy is -0-C 6 -C 12 aryl, for example phenoxy or naphthoxy, preferably phenoxy.
• dC 12 alkylthio is -S- dralkyl, in particular -S- r C 4 alkyl.
• C 6 -C 12 arylthio is -0-C 6 -C 12 aryl, for example phenylthio or naphthylthio, preferably phenylthio.
• C 2 -C 24 dialkylamino is N (alkyl 1 ) (alkyl 2 ), the sum of the carbon atoms in the two groups alkyl and alkyl 2 being from 2 to 24, preferably N (C 1 -C 4 alkyl) -C 1 -C 4 alkyl.
• C 7 -C 4 alkylarylamino is N (alkyl 1 ) (aryl 2 ), the sum of the carbon atoms in the two groups alkyl and aryl 2 being from 7 to 24, for example methylphenylamino, ethylnaphthylamino or butylphenanthrylamino, preferably methylphenylamino or ethylphenylamino.
• Ci 2 -C -diarylamino is N (aryl 1 ) (aryl 2 ), the sum of the carbon atoms in the two groups Aiyh and aryl 2 being from 12 to 24, for example diphenylamino or phenylnaphthylamino, preferably diphenylamino.
• Halogen means for example fluorine, chlorine, bromine, iodine. Halogen is preferably chlorine.
• Preferred latent pigments are compounds of the formula (I), such as perylene carboximides of the formulas Via or VIb
• D is hydrogen, dC 6 -alkyl, unsubstituted or substituted by halogen or dC 6 -alkyl phenyl, benzyl or phenethyl or B,
• R 15 and R 16 are independently hydrogen, halogen, CrC 24 alkyl, CrC ⁇ alkoxy or phenyl, or
• R 73 to R 76 independently of one another are hydrogen, halogen, -COO-C C 5 -alkyl or
• R ⁇ 7 is hydrogen, halogen or CrC 2 alkyl
• R 18 , R 19 and R 20 are independently hydrogen, halogen, dd-alkyl, C r C 4 - alkoxy, NECOd-C 4 alkyl, NECOPhenyl or NH-E
• at least one of the radicals R 18 , R 19 or R 20 are NECOd-C 4 -alkyl, NECOPhenyl or NH-E
• R ⁇ is hydrogen, CC 24 alkyl, benzyl or a group
• R 23 represents hydrogen, E or R 21 ,
• R 2 , R 25 , R 26 and R 27 independently of one another are hydrogen, CrC 24 alkyl, CC 6 alkoxy,
• R 28 and R 29 are independently hydrogen, halogen or d-C ⁇ -alkyl, or
• R 30 , R 31 and R 32 independently of one another are hydrogen, halogen, dC 6 -alkoxy, d-C ⁇ -alkyl, trifluoromethyl, nitro, acetyl, CONR 7 R 33 or S ⁇ 2 NR 7 R 33 , and R 33 for hydrogen, Halogen, CC 6 alkyl or unsubstituted or substituted with hydrogen or mono-, di- or trisubstituted by halogen, nitro, E, CONER 85 , NECO-R 85 , trifluoromethyl, d-C ⁇ -alkoxy or d-C ⁇ -alkyl ,
• R M is hydrogen, CN, d-C ⁇ -alkyl, dC 6 -alkoxy or halogen,
• R 35 and R 36 are independently hydrogen, halogen, d-C ⁇ -alkyl, dC 6 -alkoxy, nitro, acetyl or S ⁇ 2 NE-dC 6 -alkyl,
• R ⁇ 6 represents the same as R 30 or represents a radical, phenoxy or an ester, COO (d-C ⁇ -alkyl),
• R 87 is the same as R 31 or for a radical, NECO-phenyl,
• Aryl means for example heteroaryl or for example phenyl, phenanthryl or naphthyl, or
• R 89 is hydrogen, d-C ⁇ -alkoxy, dC 6 -alkyl or 1-naphthyl,
• Rso is hydrogen, dC 6 -alkoxy, dC 6 -alkyl, halogen, NECO-d-C ⁇ -alkyl, or unsubstituted, or with dC 6 -alkyl, dC 6 -alkoxy, mono-, di- or trisubstituted by halogen Phenacyl, with particular preference being given to the single or double substitution by Cl and
• R 91 is hydrogen, halogen, dC 6 -alkoxy, dC 6 -alkyl, NO 2 , or independently of one another the same meaning as R ⁇ 7 and R ⁇ s, or a group
• XVII is a pigment of the Color Index, PY 93, PY 94, PY95, PY 128 or PY 166, or
• XVIIIc where in XVIIIb when E is hydrogen, XVIIIb is pigment color index PR 144, PR 166, PR 214, PR 220, PR 221 or PR 242, and XVIIIc when E is hydrogen, XVIIIc is Pigment Color Index PO 31, R 37 and RM independently of one another are hydrogen, halogen, nitro, CrC 6 alkoxy, C 1 -C 6 alkyl, trifluoromethyl, CONER 45 or SO 2 NER 5 , but at least once CONER 45 or SO 2 NER 45 , and
• R 39 and R 10 are independently of one another hydrogen, halogen, nitro, dC 6 alkoxy or CrC ⁇ alkyl,
• R 40 , R ⁇ and R 42 independently of one another hydrogen, halogen, nitro, acetyl, dC 6 -alkoxy,
• R 3 and R ⁇ independently of one another hydrogen, halogen, Ci-C ⁇ -alkoxy or
• R 5 is hydrogen, halogen, dd-alkyl or unsubstituted or substituted by 1 to 3, preferably 2, substituents such as halogen, nitro, trifluoromethyl, dd-alkoxy or dC 4 -alkyl, E, preferably chlorine or methyl
• R 95 represents hydrogen or OCH 3 ,
• Rg ⁇ and R 97 independently of one another chlorine or methyl.
• R 98 , R 99 or R 100 independently of one another chlorine, methyl or COOCH 2 CH CI,
• R- ⁇ and R 78 independently of one another E, hydrogen, CrC ⁇ 2 alkyl or unsubstituted or with halogen, C ⁇ -C ⁇ alkyl, dC 6 alkoxy, nitro, acetyl, SO 2 NEd-C 6 alkyl or SO 2 NH 2 substituted C 6 -C 12 aryl,
• R 79 and R 80 independently of one another are hydrogen, halogen, d-C ⁇ -alkyl, d-C ⁇ -alkoxy, nitro, cyano, CONH 2 , SO 2 NECrC 6 -alkyl, SO 2 NH 2 , SO 3 H, SO 3 Na or unsubstituted or substituted by halogen, CC-C ⁇ alkyl d 6 alkoxy, nitro, acetyl, SO 2 NEd-C 6 alkyl or SO 2 NH 2 substituted C 6 -C 12 aryl, and
• R 81 is hydrogen, halogen, nitro, cyano, hydroxy or dC 6 alkoxy or
• YH 2 a divalent metal selected from the group Cu (ll), Zn (ll), Fe (ll), Ni (ll), Ru (ll), Rh (ll), Pd (ll), Pt (ll), Mn (II), Mg (II), Be (II), Ca (II), Ba (II), Cd (II), Hg (II), Sn (II), Co (II) or Pb (II) are preferred Cu (ll), Zn (ll), Fe (ll) Ni (ll) or Pd (ll) or mono- or divalent oxometal selected from the group V (O), Mn (O) or TiO, Z -CH (R 47 ) -, -CO- or -SO 2 -,
• R 46 is hydrogen, d-C ⁇ -alkyl, -N (E) R 47 , -NECOR 48 , -SO 2 (NH) 2 CO 2 C (CH 3 ) 3 , -COR 48 or
• R 47 is hydrogen or -C ⁇ -alkyl
• R 48 dd-alky! and R 9 is hydrogen, halogen, CrC 6 alkyl or d-C ⁇ -alkoxy, z for zero or 1, y for zero or for a number from 1 to 8, K for zero or 1, L for zero or a number of Is from 1 to 16, wherein when y is from 1 to 4, K and L are zero, or when K and L are from 1 to 16, y is zero, and
• L T and L 2 each bonded to one of the 8 nitrogen atoms forming the phthalocyanine complex and / or to one of the 8 carbon atoms forming the phthalocyanine complex, independently of one another denote hydrogen, halogen, d-Ci ⁇ -alkoxy, CrC ⁇ 8 alkylthio, CrC ⁇ 8 - Alkylamino, C 2 -C 18 -dialkylamino, morpholine or for unsubstituted or substituted with dC 12 -alkyl piperidine, and
• T for each T independently of one another halogen, dC 18 alkyl, d -CC 8 alkoxy, dC 18 - alkylthio or C 2 -C 8 dialkylamino, and
• R 50 and R 51 independently of one another are hydrogen, halogen, CrC 24 alkyl, CrC 6 alkoxy,
• R 52 and R ⁇ independently of one another are hydrogen, halogen, CrC 6 alkyl, C r C 6 alkoxy or -
• CN, R ⁇ and R 55 are independently hydrogen, halogen or CrC 6 alkyl and
• R 56 hydrogen or dd-alky! mean, wherein in the formulas mentioned above E is hydrogen or B, with the
• E is B at least once in each formula, and for B those mentioned above
• R 18 , R 19 and R 20 independently of one another dC -alkoxy
• R 28 and R 29 are independently hydrogen, halogen or dd-alkyl
• R30, R31 and R 3 independently of one another are hydrogen, halogen, CrC 6 alkoxy, CrC 6 alkyl,
• R 3 3 represents hydrogen, halogen, CrC 6 alkyl or unsubstituted or substituted with hydrogen, halogen, nitro, E, CrC 6 alkoxy or d-C ⁇ -alkyl, or
• R ⁇ and Rs ⁇ independently of one another hydrogen, halogen, CrC 6 alkoxy, -C-C 6 alkyl,
• R 6 ⁇ and R 62 are independently hydrogen, chlorine, CONER ⁇ or SO 2 NER 66, at least once CONER ⁇ or SO 2 denote NER ⁇ ,
• R 39 for hydrogen, chlorine or methyl
• R ⁇ 3 , R & 4 and R 65 independently of one another are hydrogen, chlorine, methoxy, methyl, or at least once CONER ⁇ or SO 2 NER ⁇ , and
• R ⁇ for unsubstituted or with 1 to 3 substituents selected from the group consisting of chlorine, trifluoromethyl, methoxy, methyl or E substituted phenyl or
• Z is -CO-or -SO 2 -, and z is zero or 1 and y is a number from 1 to 4,
• Carbon atoms independently of one another, denote hydrogen, C 2 -C 18 dialkylamino,
• Morpholine or unsubstituted or substituted with CrC ⁇ 2 alkyl piperidine in particular piperidine substituted with CrC ⁇ 2 alkyl, and very particularly 4-n-propylpiperidine, and
• Rsound R 51 is independently hydrogen, halogen, dC 4 alkyl, CrC 6 alkoxy,
• R 52 and R 53 are hydrogen and Rs ⁇ are hydrogen, methyl or ethyl, and where E in the formulas is each hydrogen or B, with the proviso that E is at least once B in each formula, and B the above-mentioned preferences apply.
• R ⁇ and R 67 independently of one another are hydrogen, methyl, tert-butyl, chlorine, bromine,
• E denotes hydrogen or B, with the proviso that E is at least once B and B has the meaning of the last-mentioned preference, and
• R M is hydrogen, halogen, -C ⁇ alkoxy, d-C ⁇ alkyl,
• R 69 is CrC ⁇ alkoxy, especially methoxy
• R 70 is CONHE, SO 2 NMeE or SO 2 NHE, in particular SO 2 NHE or SO 2 NMeE, and
• Azo compounds such as mono- and bis-azo compounds of the formulas LX, LXI, XXXV, XXXVa, XXXVIa or XXXVIb
• E is -COO-C (CH 3 ) 2 -CH 2 CH 3 or -COO-C (CH 3 ) 3 and
• R 71 is chlorine or methyl, and R ⁇ 2 , R ⁇ 3 , R M and R 6 s have the meanings given above, and
• Phthalocyanines of the formula XXI with the last-mentioned preferences,
• E is hydrogen or B, with the proviso that E is at least once B and B has the meaning of the last-mentioned preference.
• the compounds XXXIVc, XXXIVd and XXXVa are still new and also an object of this invention and methods for their preparation by reacting a pigment of the formulas XXXIVd, XXXIVdl or XXXVal
• R 69 and R 70 correspond to the latter preferences, provided that E is hydrogen and
• compounds of the formulas XXXIV c, XXXIVd or XXXVa are prepared by the general process for the preparation of latent pigments, as described in US Pat. No. 5,484,943 and 5,615,725, by Pigment of the formulas XXXIV d, XXXIVdl or XXXVal with a reactive bond of B, which causes the formulas Cl-B or BOB to react.
• B particularly preferably represents di-tert-alkyl carbonate such as, for example, di-tert-butyl or di-tert-amyl carbonate.
• reaction can be carried out in the presence of an organic solvent, preferably in aprotic ones such as tetrahydrofuran.
• the reaction is usually carried out with the addition of an organic base such as, for example, nitrogen-containing bases such as triethylamine, dimethylaminopyridine, preferably with dimethylaminopyridine.
• an organic base such as, for example, nitrogen-containing bases such as triethylamine, dimethylaminopyridine, preferably with dimethylaminopyridine.
• the compounds of the formulas XXXIV c, XXXIVd or XXXVa are used to prepare the pigment dispersions according to the invention.
• the present invention further relates to pigment dispersions containing
• Non-water-containing or water-containing solvent and polymer correspond to the definitions of the method according to the invention given above.
• the pigment dispersions according to the invention can be prepared in accordance with the method according to the invention, or can be prepared directly from the pigments by mechanical comminution and subsequent selection techniques, such as described in US Pat. No. 4,597,794, 5,085,698, 5,030,669 or WO 96/14925, according to the process according to the invention Filtration or centrifugation to remove coarse particles with the addition of stabilizing copolymers.
• organic pigments of the pigment dispersions according to the invention are compounds of the formula (LXII)
• a and x correspond to the meaning given in formula (I), and (K) for hydrogen or a cation of an alkali metal such as Li + , Na + , K + , an alkaline earth metal such as Mg ++ 2 , Ca ++ y 2 ,
• the pigment dispersions according to the invention can also contain the organic pigments colloidally embedded in the polymer and / or solvent and / or in solution.
• the present invention therefore further relates to the pigment dispersions according to the invention which contain a pigment in colloidal form.
• the present invention preferably relates to a pigment dispersion comprising
• the present invention also relates to the pigment dispersions obtainable by the processes according to the invention.
• the pigment dispersions according to the invention can, if desired, be used in further formulation or conditioning for special applications.
• the present invention therefore also relates to the use of the pigment dispersions according to the invention and the compounds XXXIVc, XXXIVd or XXXVa, or the pigment form obtainable from these compounds, for dyeing / pigmenting high-molecular material, which can be organic or inorganic in nature and mean plastics and / or natural substances can.
• the compounds XXXIV c, XXXIVd or XXXVa can be converted into the pigment form by generally known methods, such as by thermal, chemical or photolytic treatment, as described, for example, in EP-A 654 711 or EP-A-742255.
• the high molecular weight materials can be, for example, natural resins or dry oils, rubber or casein or modified natural substances such as chlorinated rubber, oil-modified alkyd resins, viscose, cellulose ethers or esters such as ethyl cellulose, cellulose acetate, propionate, or butyrate, celulose and nitro cellulose , act, but in particular fully synthetic organic polymers (thermosets and thermoplastics), as can be obtained by polymerization, for example by polycondensation or polyaddition.
• natural resins or dry oils rubber or casein or modified natural substances such as chlorinated rubber, oil-modified alkyd resins, viscose, cellulose ethers or esters such as ethyl cellulose, cellulose acetate, propionate, or butyrate, celulose and nitro cellulose , act, but in particular fully synthetic organic polymers (thermosets and thermoplastics), as can be obtained by polymerization, for example by polycondensation
• the class of the polymers includes, for example, polyolefins such as polyethylene, polypropylene, polyisobutylene, further substituted polyolefins, such as polymers of monomers such as vinyl chloride, vinyl acetate, styrene, acrylonitrile, acrylic acid esters, methacrylic acid esters, fluoropolymerizates such as, for example, polyfluorethylene, polytrifluorochloroethylene or tetrafluoropropylene / copolymerized hexafluoropropylene / hexafluoropropylene / copolymerized hexafluoropropylene of the monomers mentioned, in particular ABS (acrylonitrile / butadiene / styrene) or EVA (ethylene / vinyl acetate).
• polyolefins such as polyethylene, polypropylene, polyisobutylene
• further substituted polyolefins such as polymers of mono
• polyesters both saturated such as alkyd resins, and unsaturated such as maleic resins, also linear polyesters, polyamides, polyurethanes, polycarbonates, polyphenylene oxides or silicones, silicone resins.
• the high molecular weight compounds mentioned can be present individually or in mixtures as plastic compositions, melts or in the form of spinning solutions, lacquers or printing inks. Depending on the intended use, it proves advantageous to use the disperse pigment concentrates according to the invention as toners or in the form of preparations.
• the present invention therefore preferably relates to the use of the pigment dispersions according to the invention and a compounds XXXIVc, XXXIVd or XXXVa or the pigment form obtainable from these compounds or the compositions according to the invention containing high molecular weight material, in particular high molecular weight organic material, and a dye-effective amount of the compounds of the formulas XXXIVc, XXXIVd or XXXVa, or the pigment form obtainable from these compounds, or the pigment dispersions according to the invention for the production of inks or printing inks in printing processes for flexographic printing, screen printing, packaging printing, security color printing, gravure printing or offset printing, for prepress and for textile printing, for office and home applications or graphic applications, for paper goods, for ballpoint pens, felt-tip pens, fiber pens, cardboard, wood, (wood) stains, metal, ink pads or inks for impact printing processes (with impact printing bracelets), or for the production of
• Toners or polymeric color particles for the production of toners for dry copy toners and liquid copy toners or electrophotographic toners can be produced in master batches and in turn can be used in master batches for the production of colored plastics.
• the invention further relates to compositions comprising high molecular weight material, in particular high molecular weight organic material, and a dye-effective amount of the compounds of the formulas XXXIVc, XXXIVd or XXXVa, or the pigment form obtainable from these compounds, or the pigment dispersions according to the invention.
• organic substances with the compounds obtained according to the invention for example, such a compound is admixed to these substrates, if appropriate in the form of masterbatches, using rolling mills, mixing or grinding apparatus.
• the pigmented material is then brought into the desired final shape by methods known per se, such as calendering, pressing, extrusion, painting, casting or injection molding.
• plasticizers for example, esters of phosphoric acid, phthalic acid or sebacic acid can serve as such.
• the plasticizers can be incorporated into the polymers before or after the incorporation of the compounds obtained according to the invention. It is also possible to add fillers or other coloring constituents, such as white, colored or black pigments, to the high molecular weight, organic substances in addition to the compounds obtained according to the invention in order to achieve different colors.
• the high molecular weight organic materials and the pigment dispersions obtained according to the invention are optionally finely dispersed or dissolved together with additives such as fillers, other pigments, siccatives or plasticizers in a common organic solvent or solvent mixture. You can do this by dispersing or dissolving the individual components for yourself or several together, and only then bringing all the components together.
• the present invention therefore furthermore relates to a process for the preparation of the compositions according to the invention by reacting high molecular weight organic material with a dye-effective amount of the pigment dispersion according to the invention or compounds of the formulas XXXIVc, XXXIVd or XXXVa or the pigment form obtainable from these compounds.
• the weight ratio of the pigment dispersions according to the invention or of the compounds of the formulas XXXIVc, XXXIVd or XXXVa, or of the pigment form obtainable from these compounds, to the compositions according to the invention is expediently in the range from 0.001 to 75% by weight, preferably from 0.01 to 50% by weight. %, based on the total weight of the composition.
• the present invention further relates to inks which consist of the compositions according to the invention.
• the inks can be produced, for example, by mixing the pigment dispersions according to the invention or the compounds of the formulas XXXIVc, XXXIVd or XXXVa, or the pigment form obtainable from these compounds, with polymeric dispersants.
• the pigment dispersion is mixed with the polymeric dispersant using the generally known methods of mixing, such as stirring or mixing, and it is preferable to use intensive mixers such as Ultraturax.
• the compounds of the formulas XXXIVc, XXXIVd or XXXVa are generally mixed before, during or after mixing with a polymeric dispersant generally known methods, such as thermal, chemical or photolytic methods, converted to the corresponding pigment.
• the pigment concentration of the ink is expediently generally in the range from 0.001 to 75% by weight, preferably from 0.01 to 50% by weight, based on the total weight of the ink.
• polymeric dispersants are polyacrylic resins containing carboxylic acid groups, such as polymeric methacrylic or crotonic acids, in particular those obtained by polymerizing acrylic acid or acrylic acid and other acrylic monomers such as acrylic acid esters.
• a small proportion of a water-dilutable organic solvent in 0.01 to 30% by weight, based on the total weight of the ink and / or water and / or bases, can be mixed in, so that a pH in the range from 7 to 11 is reached. It may also be advantageous to add, for example, preservatives, anti-foaming agents, surfactants, light stabilizers and pH regulators to the printing ink according to the invention.
• Suitable pH regulators are, for example, inorganic salts such as lithium hydroxide or carbonate, quaternary ammonium hydroxide or carbonate.
• preservatives and antifoams are, for example, sodium dehydroacetate, 2,2-dimethyl-6-acetoxydioxane or ammonium thioglycolate.
• Known agents described in US Pat. No. 5,106,417 which regulate the viscosity or the surface tension can also be used.
• Water-dilutable organic solvents are, for example, aliphatic dC 4 alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol, tert-butanol, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or diacetone alcohol, and also polyols, cellosolves and carbitols such as ethylene glycol, diethylene glycol, triethylene glycol, glycerol, Propylengylkol, ethylene glycol monomethyl or monoethyl ether, propylene glycol methyl ether, dipropylene glycol methyl ether, tripropylene glycol methyl ether, ethylene glycol phenyl ether, propylene glycol phenyl ether, diethylene glycol monomethyl or monoethyl ether, Diethylenglykolmonobutylether.Triethyleng
• the working up is carried out according to the usual methods for working up dispersions by separation processes such as sieving or centrifuging the coarse particles from the dispersion obtained. It has proven advantageous to centrifuge in two stages of different intensities. First at 10 minutes to 1 hour at 2000 to 4000 rpm and then at 10 minutes to 1 hour at 6000 to 10000 rpm.
• the dispersion After centrifugation or sieving, the dispersion can be used directly as an ink for, for example, inkjet printing.
• the present invention therefore also relates to a process for the preparation of inks by mixing high molecular weight organic material and a dye-effective amount of the disperse pigment dispersion according to the invention or of the compounds of the formulas XXXIVc, XXXIVd or XXXVa, or of the pigment form obtainable from these compounds.
• the present invention relates to the use of a high-molecular material pigmented according to the invention containing the pigment dispersion according to the invention, in particular the pigment dispersions containing organic solvents, for the production of color filters.
• the present invention relates to a process for the production of color filters containing a transparent substrate and a red, blue and green layer applied thereon in any order, by using a respectively colored pigment dispersion according to the invention for the production of the red, blue and green layers, or this Layers contain a corresponding colored compound XXXIVc, XXXIVd or XXXVa or pigment form obtainable from a compound XXXIVc, XXIVd or XXXVa or a composition according to the invention.
• the differently colored layers preferably have such patterns that they do not overlap on at least 5% of their surface and very particularly preferably do not overlap.
• the manufacture and use of color filters or brightly pigmented, high-molecular organic materials are described in Displays 14/2, 1151 (1993), Journal of the SID / 3, 341-346 (1993) or at IDW'95 (contribution CF-3, Pages 57-60 of the printed version) or Journal of Photopolymer Science and Technology 9/1, 109-120 (1196) and in Nippon Steel Corp. , Application JP 09176511-A, Primary Accession No. 97-399776 / 37, Pigment dispersion compositions for color resist inks, Asahi Glass Co.
• the color filters can be produced, for example, using inks, in particular printing inks, which contain the pigment dispersions according to the invention, or, for example, by mixing a pigment dispersion according to the invention with chemically, thermally or photolytically structurable high molecular material (resist).
• the further production can be carried out, for example, analogously to EP-A 654 711, by application to a substrate, such as, for example, an LCD, subsequent photostructuring and development.
• the pigment dispersions according to the invention which have non-aqueous solvents or dispersion media for polymers are particularly preferred for the production of color filters.
• the invention further comprises a transparent substrate, each containing a red, blue and green layer, each containing a correspondingly colored pigment dispersion according to the invention or a compound XXXIVc, XXXIVd or XXXVa or the pigment form obtainable from a compound XXXIVc, XXXIVd or XXXVa or a composition according to the invention pigmented high molecular weight organic material, is coated.
• the order of the coating is usually irrelevant.
• the differently colored layers preferably have such patterns that they do not overlap, particularly preferably do not overlap, on at least 5% of their area.
• the present invention also includes color filters containing a transparent substrate and a red, blue and green layer applied thereon, each obtainable from a correspondingly colored pigment dispersion according to the invention or a compound XXXIVc, XXXIVd or XXXVa or containing those obtainable from a compound XXXIVc, XXXIVd or XXXVa Pigment form or a composition according to the invention.
• the present invention relates to toners containing a pigment dispersion according to the invention or a compound XXXIVc, XXXIVd or XXXVa or the pigment form obtainable from a compound XXXIVc, XXXIVd or XXXVa or a composition according to the invention containing pigmented high molecular weight organic material in a color-effective amount.
• the present invention relates to processes for the production of toner by adding a high molecular weight organic material and a dye-effective amount of the disperse pigment dispersion according to the invention or the compound of the formulas XXXIVc, XXXIVd or XXXVa, or the pigment form pigment form obtainable from these compounds or a composition according to the invention, containing pigmented high molecular material, mixed together.
• toners, lacquers, inks or colored plastics are produced by mixing in masterbatches using rolling mills, mixing or grinding apparatus.
• the present invention relates to colorants containing a pigment dispersion according to the invention or a compound XXXIVc, XXXIVd or XXXVa or the pigment form obtainable from a compound XXXIVc, XXXIVd or XXXVa or a composition according to the invention containing pigmented high molecular weight organic material in an amount which is effective for coloring.
• the present invention relates to colored plastics or polymeric color particles containing a pigment dispersion according to the invention or a compound XXXIVc, XXXIVd or XXXVa or that from a compound XXXIVc, XXXIVd or XXXVa Available pigment form or a composition according to the invention, containing pigmented high molecular weight organic material in a dye-effective amount.
• the present invention relates to non-impact printing material containing a pigment dispersion according to the invention or a compound XXXIVc, XXXIVd or XXXVa or the pigment form obtainable from a compound XXXIVc, XXXIVd or XXXVa or a composition according to the invention containing pigmented high molecular weight organic material in a dye-effective Quantity.
• the present invention relates to a process for the production of non-impact printing material by using a high molecular weight organic material and a dye-effective amount of the disperse pigment dispersion according to the invention or the compound of the formulas XXXIVc, XXXIVd or XXXVa, or the pigment form obtainable from these compounds Pigment form or a composition according to the invention, containing pigmented high molecular material, mixed together.
• a dye-effective amount of the disperse pigment dispersion according to the invention or the compound of the formulas XXXIVc, XXXIVd or XXXVa, or the pigment form pigment form obtainable from these compounds or a composition according to the invention containing pigmented high molecular weight material generally means 0.0001 to 99.99% by weight. %, preferably 0.001 to 50% by weight and particularly preferably 0.01 to 50% by weight, based on the total weight of the material pigmented therewith.
• the process according to the invention produces very fine pigment dispersions without the high energy, time and apparatus requirements required for grinding and evaporation techniques.
• the pigment dispersions are characterized by high stability and transparency and have excellent coloristic and application properties. They are particularly suitable for the production of inks and color filters that have high color strengths, brilliance and transparency.
• the polymer After decanting the methanol, the polymer is washed with another portion of methanol. Finally, the polymer is dried in a desiccator over potassium hydroxide.
• the polymer has a molecular weight (number average) of 16000, determined by gel permeation chromatography. The ratio Mw / Mn (mass average / number average) is 1.94.
• the latent pigment solution is added to the polymer solution and the resulting yellow mixed solution is evaporated to dryness on a rotary evaporator under reduced pressure and a maximum temperature of 60 ° C.
• the resulting solid mixture is dried in vacuo at 60 ° C. for 14 hours and then exposed to a temperature of 140 ° C. in a preheated oven for 2 hours. After this heat treatment, the color of the solid mixture changes from yellow to red.
• the solid mixture is cooled to room temperature and provided with 20 ml of dioxane.
• the polymer is dissolved by ultrasound treatment while the generated pigment is dispersed. 700 microliters of morpholine and 20 ml of water are added in succession to the resulting dispersion.
• dioxane is distilled off on a rotary evaporator at reduced pressure, and the red dispersion is concentrated to 20.7 g.
• the resulting dispersion is homogeneous and transparent. It has a viscosity of 2.16 mPas at 25 ° C. There is no tendency to precipitate after several days.
• the latent pigment solution is added to the polymer solution and the resulting yellow mixed solution is evaporated to dryness on a rotary evaporator under reduced pressure ( ⁇ 1 mPa) and a maximum temperature of 60 ° C. for one hour.
• the solid mixture is exposed to a temperature of 140 ° C in a preheated oven for one hour. After this heat treatment, the color of the solid mixture changes from yellow to red.
• the solid mixture is cooled to room temperature and provided with 20 ml of dioxane.
• the polymer is dissolved by ultrasound treatment while the generated pigment is dispersed. 2 ml of morpholine and 30 ml of water are successively added to the resulting dispersion.
• dioxane is distilled off on a rotary evaporator at reduced pressure, and the red dispersion is concentrated to 20 g.
• the resulting dispersion is homogeneous and transparent. It has a viscosity of 6 mPas at 25 ° C. There is no tendency to precipitate after several days.
• 500 mg of the latent pigment of the formula XXXVII is dissolved in 15 ml of 1,4-dioxane and mixed with a solution of 1.5 g of the copolymer described in Example 1 in 20 ml of dioxane.
• the clear yellow solution is evaporated to dryness on a vacuum rotary evaporator and then dried further in a drying cabinet at approx. 200 torr and 60 ° C. for 15 hours.
• the resulting product is then heated in a forced-air drying cabinet at 140 ° C. for 2 hours.
• 20 ml of dioxane are added and the polymer is dissolved by ultrasound treatment and at the same time the regenerated pigment is dispersed.
• XXXVIII To a suspension of 10 g (17.8 mmol) XXXVIII, in which E has the meaning of H, Cl. Pigment Red 185, 1.53 g (12.5 mmol) of dimethylaminopyridine and 27.25 g (125 mmol) of di-tert-butyl dicarbonate are added to 250 ml of tetrahydrofuran. After stirring overnight at room temperature, the reaction mixture is filtered over MgSO 4 and the filtrate is concentrated. The concentrate is diluted with hexane, mixed intensively and the precipitated crude product is filtered, washed with hexane and then dried.
• thermogravimetric analysis of the decay shows an average decay temperature of 164.0 ° C; 46.6%, ⁇ M experimental 43.5%,
• Copolymers of 75% styrene and 25% maleic anhydride (acid number 275, from Scientific
• the dioxane is then evaporated off and the dispersion is concentrated to 20 g, corresponding to a pigment concentration of 1.33 percent by weight, based on the total weight of the dispersion.
• the resulting blue-red dispersion has a viscosity of 4.5 mPas at 25 ° C.
• a sample is diluted 40-fold with water and the transmission spectrum is measured in a 1 mm cuvette. At the maximum (520 nm) the absorption is 1.42, while at 660 nm it is only 0.1, which indicates fine particles with good transparency. Electron microscope images also show that all particle dimensions are below 0.5 micrometers.
• Thermogravimetric analysis of the decay shows an average temperature of 152.9 ° C; 49.9%, ⁇ M e ⁇ perim ⁇ ntielF 49.5%.
• thermogravimetric analysis of the decay shows an average decay temperature of 160.0 ° C;
• the solid After cooling, the solid is redispersed in 30 ml of dioxane, and then 6.5 g of N, N'-dimethylaminoethanol and 40 ml of water added, and the homogeneous dispersion is concentrated on a vacuum rotary evaporator to 33 g.
• a sample of the dispersion is diluted 100 times with water and the transmission spectrum is measured in a 1 mm cuvette. At the maximum (light wave 572 nm) the absorption is 1.21, while at 650 nm it is below 0.1, which indicates fine particles with good transparency.
• Example 2 2.8 g of the pigment dispersion of Example 2 are mixed with 0.7 g of a 2% strength (by weight) solution of a surfactant (Fluorad FC-171 from 3M Inc.) dissolved in diethylene glycol.
• a surfactant Fluorad FC-171 from 3M Inc.
• the resulting ink is tested in a "QuietJef (Hewlett-Packard) thermal inkjet printer equipped with a plastic device designed to hold the ink. Clear, clear print quality and surface coverage with a maximum optical density of 0.5 are obtained (measured This value is measured with a spectrophotometer in reflection mode, which is subtracted from the reflection of the paper. The ink shows no tendency to "bleed out" or penetrate through commercially available copy paper.
• Example 13 The ink shows no tendency to "bleed” or penetrate through commercially available copy paper.

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