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1. WO2000039221 - IMPROVED METHOD FOR PRODUCING THERMALLY CLEAVABLE, SOLUBLE PIGMENT DERIVATIVES

Publication Number WO/2000/039221
Publication Date 06.07.2000
International Application No. PCT/EP1999/010006
International Filing Date 16.12.1999
Chapter 2 Demand Filed 02.05.2000
IPC
C07D 487/22 2006.01
CCHEMISTRY; METALLURGY
07ORGANIC CHEMISTRY
DHETEROCYCLIC COMPOUNDS
487Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/-C07D477/183
22in which the condensed system contains four or more hetero rings
C09B 43/136 2006.01
CCHEMISTRY; METALLURGY
09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES; MORDANTS; LAKES
43Preparation of azo dyes from other azo compounds
12by acylation of amino groups
136with polyfunctional acylating agents
C09B 43/26 2006.01
CCHEMISTRY; METALLURGY
09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES; MORDANTS; LAKES
43Preparation of azo dyes from other azo compounds
18by acylation of hydroxy groups
26with polyfunctional acylating agents
C09B 47/24 2006.01
CCHEMISTRY; METALLURGY
09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES; MORDANTS; LAKES
47Porphines; Azaporphines
04Phthalocyanines
08Preparation from other phthalocyanine compounds
24Obtaining compounds having -COOH or -SO3H radicals, or derivatives thereof, directly bound to the phthalocyanine radical
C09B 47/26 2006.01
CCHEMISTRY; METALLURGY
09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES; MORDANTS; LAKES
47Porphines; Azaporphines
04Phthalocyanines
08Preparation from other phthalocyanine compounds
24Obtaining compounds having -COOH or -SO3H radicals, or derivatives thereof, directly bound to the phthalocyanine radical
26Amide radicals
C09D 11/32 2014.01
CCHEMISTRY; METALLURGY
09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
DCOATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
11Inks
30Inkjet printing inks
32characterised by colouring agents
CPC
C09B 47/24
CCHEMISTRY; METALLURGY
09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES ; , e.g. PIGMENTS; MORDANTS; LAKES
47Porphines; Azaporphines
04Phthalocyanines ; abbreviation: Pc
08Preparation from other phthalocyanine compounds ; , e.g. cobaltphthalocyanineamine complex
24Obtaining compounds having —COOH or —SO3H radicals, or derivatives thereof, directly bound to the phthalocyanine radical
C09B 47/26
CCHEMISTRY; METALLURGY
09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES ; , e.g. PIGMENTS; MORDANTS; LAKES
47Porphines; Azaporphines
04Phthalocyanines ; abbreviation: Pc
08Preparation from other phthalocyanine compounds ; , e.g. cobaltphthalocyanineamine complex
24Obtaining compounds having —COOH or —SO3H radicals, or derivatives thereof, directly bound to the phthalocyanine radical
26Amide radicals
C09D 11/32
CCHEMISTRY; METALLURGY
09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
DCOATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
11Inks
30Inkjet printing inks
32characterised by colouring agents
C09D 7/41
CCHEMISTRY; METALLURGY
09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
DCOATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
7Features of coating compositions, not provided for in group C09D5/00
40Additives
41Organic pigments; Organic dyes
G03F 7/0007
GPHYSICS
03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR;
7Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
0005Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
0007Filters, e.g. additive colour filters; Components for display devices
G03F 7/029
GPHYSICS
03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR;
7Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
004Photosensitive materials
027Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
028with photosensitivity-increasing substances, e.g. photoinitiators
029Inorganic compounds; Onium compounds; Organic compounds having hetero atoms other than oxygen, nitrogen or sulfur
Applicants
  • CIBA SPECIALTY CHEMICALS HOLDING INC. [CH/CH]; Klybeckstrasse 141 CH-4057 Basel, CH (AllExceptUS)
  • SCHACHT, Hans-Thomas [DE/DE]; DE (UsOnly)
  • SREENIVASAN, Ramaswami [IN/IN]; IN (UsOnly)
  • CHANDRASEKHAR, Mudaliar, Dayal [IN/IN]; IN (UsOnly)
  • MOEGLE, Gilbert [FR/FR]; FR (UsOnly)
  • WAGNER, Barbara [DE/DE]; DE (UsOnly)
  • MONNIER, Charles, Edward [CH/CH]; CH (UsOnly)
Inventors
  • SCHACHT, Hans-Thomas; DE
  • SREENIVASAN, Ramaswami; IN
  • CHANDRASEKHAR, Mudaliar, Dayal; IN
  • MOEGLE, Gilbert; FR
  • WAGNER, Barbara; DE
  • MONNIER, Charles, Edward; CH
Common Representative
  • CIBA SPECIALTY CHEMICALS HOLDING INC.; Patentabteilung Klybeckstrasse 141 CH-4057 Basel, CH
Priority Data
2585/9829.12.1998CH
Publication Language German (DE)
Filing Language German (DE)
Designated States
Title
(DE) VERBESSERTES VERFAHREN ZUR HERSTELLUNG THERMISCH SPALTBARER, LÖSLICHER PIGMENTDERIVATE
(EN) IMPROVED METHOD FOR PRODUCING THERMALLY CLEAVABLE, SOLUBLE PIGMENT DERIVATIVES
(FR) AMELIORATION APPORTEE A UN PROCEDE POUR PRODUIRE DES DERIVES DE PIGMENTS SOLUBLES, POUVANT ETRE DECOMPOSES THERMIQUEMENT
Abstract
(DE)
Die Erfindung betrifft ein Verfahren zur Herstellung einer Verbindung der Formel A(D)x(E)y durch Reaktion einer Verbindung der Formel A(H)x(H)y mit einem Pyrokohlensäurediester der Formel (I), worin x und y unabhängig voneinander je eine ganze Zahl von 0 bis 6 bedeuten, jedoch nicht gleichzeitig x und y die Zahl 0, A für den Rest eines Chromophors der Chinacridon-, Anthrachinon-, Perylen-, Indigo-, Chinophthalon-, Indanthron-, Isoindolinon-, Isoindolin-, Dioxazin, Azo-, Phthalocyanin- oder Diketopyrrolopyrrol-reihe-steht, der über ein oder mehrere N-Atome mit x Gruppen D und über ein oder mehrere O-Atome mit y Gruppen E verbunden ist, wobei diese N-Atome und O-Atome Teil des Restes A bilden, jede Gruppe D oder E unabhängig von den anderen für Wasserstoff oder eine Gruppe der Formel (II) steht, wobei mindestens eine Gruppe D oder E nicht Wasserstoff ist, und L eine beliebige, zur Solubilisierung geeignete Gruppe bedeutet, in Gegenwart einer Base als Katalysator, dadurch gekennzeichnet, dass diese Reaktion in einem aromatischen oder heteroaromatischen Lösungsmittel stattfindet, ausgewählt aus unsubstituiertem oder mit 1 bis 3 C1-C6Alkyl, Phenyl, Benzyl, C1-C6Alkoxy, Phenoxy, C1-C24Alkylthio, Halogen und/oder Nitro substituiertem Benzol, Diphenyl, Pyridin, Chinolin und Pyrrol sowie beliebigen Gemischen davon. Durch die Verwendung eines aromatischen Lösungsmittels werden vor allem Monoazo, Bisazo und Phthalocyaninpigmente mit überraschend besseren Resultaten solubilisiert. Sowohl die Ausbeute als auch die Reinheit sind deutlich höher als in den bisher bekannten Lösungsmitteln, und es lassen sich mehr solubilisierende Gruppen im Pigment einbauen. Die erfindungsgemässe Methode ist insbesondere auch vorteilhaft zur Herstellung von Latentpigmenten in grösseren Mengen geeignet.
(EN)
The invention relates to a method for producing a compound of formula A(D)x(E)y by reacting a compound of formula A(H)x(H)y, in the presence of a base which serves as a catalyst, with a diethyl pyrocarbonate of formula (I), wherein x and y, independent of one another, each represent a whole number ranging from 0 to 6, however x and y are not equal to 0 at the same time; A represents the radical of a chromophore of the quinacridone series, anthraquinone series, perylene series, indigo series, quinophthalone series, indanthrone series, isoindolinone series, isoindoline series, dioxazine series, azo series, phthalocyanine series or of the dicetopyrrolopyrrol series, which is bound to x groups D via one or more N atoms, and to y groups E via one or more O atoms, whereby these N atoms and O atoms form part of radical A; each group D or E, independent of one another, represents hydrogen or a group of formula (II), whereby at least one group D or E is not hydrogen, and L represents any group which can be solubilized. The inventive method is characterized in that this reaction takes place in an aromatic or heteroaromatic solvent, selected from benzene, diphenyl, pyridine, quinoline and pyrrole, as well as from any mixtures thereof, which is non-substituted or which is substituted with 1 to 3 C1-C6 alkyl, phenyl, benzyl, C1-C6 alkoxy, phenoxy, C1-C24 alkylthio, halogen and/or nitro. Primarily monoazo, bisazo and phthalocyanine pigments are solubilized with astonishingly improved results by using an aromatic solvent. Both the yield as well as the purity are significantly higher than those obtained using preart solvents, and it is possible to incorporate more solubilizing groups in the pigment. The inventive method is, in particular, also advantageously suited for producing latent pigments in large quantities.
(FR)
L'invention concerne un procédé pour produire un composé de formule A(D)x(E)y par réaction, en présence d'une base servant de catalyseur, d'un composé de formule A(H)x(H)y avec un diester d'acide pyrocarboxylique de formule (I), dans laquelle x et y représentent indépendamment l'un de l'autre un nombre entier compris entre 0 et 6, x et y ne valant pas simultanément 0; A représente un radical de la série quinacridone, anthraquinone, pérylène, indigo, quinophtalone, indanthrone, iso-indolinone, iso-indoline, dioxazine, azo, phthalocyanine ou dicétopyrrolopyrrol, qui est lié à x groupes D par l'intermédiaire d'un ou plusieurs atomes de N, et à y groupes E par l'intermédiaire d'un ou plusieurs atomes de O, ces atomes de N et de O formant une partie du radical A; chaque groupe D ou E représente indépendamment des autres hydrogène ou un groupe de formule (II), au moins un groupe D ou E ne représentant pas hydrogène, et L représentant un groupe quelconque pouvant être solubilisé. Ce procédé est caractérisé en ce que cette réaction a lieu dans un solvant aromatique ou hétéroaromatique, sélectionné parmi benzène, diphényle, pyridine, quinoline et pyrrol (ou des mélanges quelconques de ces derniers), non substitués ou substitués par 1 à 3 radicaux suivants: alkyle C1-C6, phényle, benzyle, alcoxy C1-C6, phénoxy, alkylthio C1-C24, halogène et/ou nitro. L'utilisation d'un solvant aromatique permet de solubiliser, avec des résultats étonnamment meilleurs, principalement des pigments monoazoïques, bisazoïques et de phthalocyanine. Aussi bien le rendement que la pureté sont nettement meilleurs qu'avec les solvants connus jusqu'à présent, et il est possible d'incorporer davantage de groupes solubilisants dans le pigment. Ce procédé peut également être mis en oeuvre de façon avantageuse pour la production de pigments latents en grandes quantités.
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