EP1606249A2 - Nouveaux composes, leur procede de preparation et leur utilisation en tant que colorants et pigments - Google Patents

Nouveaux composes, leur procede de preparation et leur utilisation en tant que colorants et pigments

Info

Publication number
EP1606249A2
EP1606249A2 EP04718971A EP04718971A EP1606249A2 EP 1606249 A2 EP1606249 A2 EP 1606249A2 EP 04718971 A EP04718971 A EP 04718971A EP 04718971 A EP04718971 A EP 04718971A EP 1606249 A2 EP1606249 A2 EP 1606249A2
Authority
EP
European Patent Office
Prior art keywords
printing
formula
alkyl
compounds
production
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP04718971A
Other languages
German (de)
English (en)
Inventor
Jean-Marie Adam
Pramod V. Dalvi
Vadiraj Subbanna Ekkundi
Jean-Pierre Bacher
Sandip Tiwari
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.)
BASF Schweiz AG
Original Assignee
Ciba Spezialitaetenchemie Holding AG
Ciba SC Holding AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Ciba Spezialitaetenchemie Holding AG, Ciba SC Holding AG filed Critical Ciba Spezialitaetenchemie Holding AG
Publication of EP1606249A2 publication Critical patent/EP1606249A2/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D211/40—Oxygen atoms
    • C07D211/44—Oxygen atoms attached in position 4
    • C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
    • 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
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/0091—Methine or polymethine dyes, e.g. cyanine dyes having only one heterocyclic ring at one end of the methine chain, e.g. hemicyamines, hemioxonol
    • 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
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
    • C09B23/04—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups one >CH- group, e.g. cyanines, isocyanines, pseudocyanines
    • 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
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/10—The polymethine chain containing an even number of >CH- groups
    • C09B23/102—The polymethine chain containing an even number of >CH- groups two heterocyclic rings linked carbon-to-carbon
    • 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
    • C09B55/00—Azomethine dyes
    • C09B55/009—Azomethine dyes, the C-atom of the group -C=N- being part of a ring (Image)
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/41—Organic pigments; Organic dyes

Definitions

  • New compounds a process for their preparation and their use as dyes and pigments
  • the present invention relates to new compounds, to their preparation and to their use in the production of coloured plastics or polymeric colour particles.
  • the subject of the present invention are compounds of formula (1 )
  • Ri is hydrogen, hydroxy, halogen, nitro, cyano, amino, carboxy, carboxylic ester, sulfo, sulfonic ester, carboxylic amide, sulfonic amide, alkoxy, aryloxy, alkylthio or arylthio,
  • X is -O-, -S-, -NH- or-N(alkyI)-
  • Y is hydrogen or carboxylic ester
  • R 2 is hydrogen, alkyl or CN
  • A is a heterocyclic or linear or polycondensed aromatic group which is unsubstituted or substituted by hydroxy alkyl, halogen, nitro, cyano, amino, acylamino, carboxylic ester, sulfonic ester, carboxylic amide, sulfonic amide, alkoxy, aryloxy, alkylthio, arylthio or phenyl, or A together with T and R 2 can form an allycyclic or heterocyclic ring.
  • an alkyl is for example a straight-chain or branched C h alky! as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, 2-pentyl, 3-pentyl, 2,2-dimethylpropyl, hexyl, hepty 1, 2,4,4-trimethylpen yl, 2-ethylhexyl or octyl, preference being given to a C ⁇ _ t alkyl.
  • an alkylthio is for example methylthio, ethylthio, propylthio, butyl- thio, heptylthio or hexylthio.
  • an alkoxy is for example a straight-chain or branched C . . . alkoxy, for example methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert.
  • n-pentyloxy 2-pentyloxy, 3-pentyloxy, 2,2-dimethylpropoxy, n-hexyloxy, n-heptyloxy, n-octyloxy, 1 , 1 ,3,3-tetr amethylbutoxy or 2-ethylhexyloxy.
  • an aryloxy is to be understood as being for example a C ⁇ - 2 ,aryl- oxy, preferably a C ⁇ -i ⁇ aryloxy radical, for example phenoxy or 4-methyl ⁇ henoxy.
  • an arylthio is for example phenylthio or napthylthio.
  • a as aromatic group includes, for example, phenylene, naphthalene, acenaphthylene, anthracene, phenanthrene, naphthacene, chrysene, pyrene or petylene.
  • W is preferably phenylene, naphthalene, anthracene, phenanthrene, perylene or pyrene, and most preferably phenylene or naphthalene.
  • a as heterocyclic group is, for instance, pyridine, pyrazine, pyrimidine, pyridazine, indole iso- i ⁇ dole, quinoline, isoquinoline, carbazole, phenothiazine, benzimidazolone, benzothiazole, pyrrolo, imidazole, pyrrolidine, piperidine, piperazine, morpholine or pyrazole.
  • Heterocyclic ring formed by A, T and R ⁇ can be for example pyridine, pyrazine, pyrimidine, pyridazine, indole isoindole, quinoline, isoquinoline, carbazole, phenothiazine, benzimidazolone, benzothiazole, pyrrolo, imidazole, pyrrolidine, piperidine, piperazine, morpholine or pyrazole.
  • an ester is for example methyl-, ethyl-, propyl- or butylester.
  • the preferred compounds of formula (1) are a) phenyl-butyrolactams of formula
  • R . and A have the meaning given under the formula (1) and Et is -CH2CH3.
  • A is preferred a group substituted by one or more electron donor groups as for example -OCrC 2 alkyl, -NHC . -C h alky!, -N(CrC 12 alky]) 2 or-SC C ⁇ 2 alkyl.
  • A is most preferred one of the following groups:
  • Alkyl means C . - ⁇ _ .2 alkyl, preferably C . -C alkyl.
  • Preferred heterocycles which are formed with A, T and R 2 are:
  • R . is hydrogen
  • R 2 is hydrogen
  • A is phenyl which is unsubstituted or substituted by nitro, methoxy, ethoxy, methylthio, chloro acetyloxy, -N(CH 3.2 or -N(C 2 H 6 ) 2 , 1-naphthyl, 9-anthracenyl, pyrene, 2-ethylcarbonyl, isoin- doline or isoindolinone
  • X is -O- or-NH-
  • Y is hydrogen or COOC 2 H 5
  • T C-
  • the most preferred compounds of formula (1) are the compounds of the formulae
  • the compounds of formula (1) according to the invention are prepared, for example, by reacting a compound of formula
  • Compounds of formula (1) can contain one or more water soluble groups as sulfonic, carboxylic or cationic groups.
  • Water soluble derivatives of compounds of formula ( ) can be used as dyestuffs for textile application, coloration of cotton, wool, polyamide and polyacrylonitrile using all the well known dyeing processes.
  • Such dyes are useful for dyeing and printing manufactured natural polymer and especially synthetic hydrophobic fibre materials, especially textile materials.
  • Textile materials composed of blend fabrics comprising such manufactured natural polymer or synthetic hydrophobic textile materials are likewise dyeable or printable with the dyes of the invention.
  • Useful manufactured natural polymer textile materials are especially cellulose acetate and cellulose triacetate.
  • Synthetic hydrophobic textile materials are especially linear aromatic polyesters, for example polyesters formed from a terephthalic acid and glycols, particularly ethylene glycol, or condensation products of terephthalic acid and 1,4-bis(hydroxymethyl)cyclohexane; polycarbo-
  • nates for example those formed from ⁇ , ⁇ -dimethyl ⁇ 4,4-dihydroxydiphenylmethane and phosgene; or fibres based on polyvinyl chloride or polyamide.
  • polyester fibres are exhaust dyed from an aqueous dispersion in the presence of customary anionic or nonionic dispersants with or without customary carriers at temperatures between 80 and 140°C.
  • Cellulose acetate is preferably dyed at between about 65 to 85°C and cellulose triacetate at up to 115°C.
  • the above dyes are also useful for dyeing by the thermosol, exhaust and continuous processes and for printing processes.
  • the exhaust process is preferred.
  • the liquor ratio depends on the apparatus, the substrate and the make-up form. However, the liquor ratio can be chosen to be within a wide range, for example in the range from 4:1 to 100:1, but it preferably is between 6:1 to 25:1.
  • the textile material mentioned may be present in the various processing forms, for example as a fibre, yarn or web or as a woven or loop-formingly knitted fabric.
  • the dyes are ground so that their particle size is on average between 0.1 and 10 microns.
  • the grinding may be effected in the presence of dispersants.
  • the dried dye is ground with a dispersant or kneaded in paste form with a dispersant and then dried under reduced pressure or by spray drying.
  • the preparations thus obtained can be used to prepare print pastes and dyebaths by adding water.
  • Printing utilizes the customary thickeners, for example modified or nonmodified natural pro- . ducts, for example alginates, British gum, gum arabic, crystal gum, carob bean flour, traga- canth, carboxymethylcellulose, hydroxyethylcellulose, starch or synthetic products, for example polyacrylamides, polyacrylic acid or copolymers thereof or polyvinyl alcohols.
  • customary thickeners for example modified or nonmodified natural pro- . ducts, for example alginates, British gum, gum arabic, crystal gum, carob bean flour, traga- canth, carboxymethylcellulose, hydroxyethylcellulose, starch or synthetic products, for example polyacrylamides, polyacrylic acid or copolymers thereof or polyvinyl alcohols.
  • the above dyes confer on the materials mentioned, especially on polyester material, level shades having very good service fastnesses, such as in particular good light fastness, especially a very good hot light fastness, fastness to dry heat setting and pleating, chlorine fastness and wet fastness such as fastness to water, perspiration and washing; the dyeings are further characterized by good rub fastness and heat stability.
  • Water insoluble derivatives of compounds of formula (1) can be used as disperse dyes for coloration of PET by exhaustion or pigments for mass coloration of plastics or can be used for inks and paints. These products can also be used for coloration of wood and metals and they are also suitable as functional dyes for special applications such as optical information storage, or display devices or printed circuit boards.
  • the present invention relates also to a process for the production of coloured plastics or polymeric colour particles, which comprises mixing together a high molecular weight organic material and a tinctorially effective amount of at least one compound of formula (1 ).
  • the present invention further relates to the use of the compounds of formula (1) individually as colourants, especially for colouring or pigmenting organic or inorganic, high-molecular- weight or low-molecular-weight material, especially high-molecular-weight organic material. It is also possible, however, for the compositions according to the invention comprising compounds of formula (1 ) to be used in the form of mixtures, solid solutions or mixed crystals.
  • Compounds of formula (1 ) can also be combined with colourants of another chemical class, for example with dyes or pigments, for example those selected from the group of the diketo- pyrrolopyrroles, quinacridones, perylenes, dioxazines, anthraquinones, indanthrones, fla- vanthrones, indigos, thioindigos, quinophthalones, isoindolinones, isoindolines, phthalocyani- nes, metal complexes, azo pigments and azo dyes.
  • dyes or pigments for example those selected from the group of the diketo- pyrrolopyrroles, quinacridones, perylenes, dioxazines, anthraquinones, indanthrones, fla- vanthrones, indigos, thioindigos, quinophthalones, isoindolinones, isoindolines, phthalocyani- nes, metal
  • the high-molecular-weight material may be organic or inorganic and may be synthetic and/or natural material.
  • the high-molecular-weight organic material usually has an average molecular weight of 10 6 -10 7 g/mol. It may be, for example, a natural resin or a drying oil, rubber or casein or a modified natural material, such as chlorinated rubber, oil-modified alkyd resins, viscose, or a cellulose ether or ester, such as ethylcellulose, cellulose acetate, propionate or butyrate, cellulose acetobutyrate or nitrocellulose, but is especially a completely synthetic organic polymer (duroplasts and thermoplasts) as may be obtained by polymerisation, for example by polycondensation or polyaddition.
  • the class of polymers includes, for example, polyolefins, such as polyethylene, polypropylene, polyisobutylene, and substituted polyole- fins, such as polymerisates of monomers such as vinyl chloride, vinyl acetate, styrene, acry- lonitrile, acrylates, methacrylates, fluoropolymers, such as polyfiuoroethylene, polytrifluoro- chloroethylene or tetrafluoroethylene/hexafluoropropylene mixed polymerisate, and copoly- merisates of the mentioned monomers, especially ABS (acrylon itrile/butadiene/styrene) or EVA (ethylene/vinyl acetate).
  • polyolefins such as polyethylene, polypropylene, polyisobutylene
  • substituted polyole- fins such as polymerisates of monomers such as vinyl chloride, vinyl acetate, styrene, acry
  • condensation products of formaldehyde with phenols the so-called phenoplasts, and condensation products of formaldehyde and urea orthiourea, also melamine, the so-called aminoplasts
  • the polyesters used as surface coating resins either saturated, such as alkyd resins, or unsaturated, such as maleic resins, and also linear polyesters, polyamides, polyurethanes, polycarbonates, polyphenylene oxides or silicones, and silicone resins.
  • the mentioned high-molecular-weight compounds may be present individually or in mixtures in the form of kneadable compounds, melts or in the form of spinning solutions.
  • They may also be present in the form of their monomers or in the polymerised state in dissolved form as film-formers or binders for paints or printing inks, such as, for example, boiled linseed oil, nitrocellulose, alkyd resins, melamine resins and urea-formaldehyde resins or acrylic resins.
  • film-formers or binders for paints or printing inks such as, for example, boiled linseed oil, nitrocellulose, alkyd resins, melamine resins and urea-formaldehyde resins or acrylic resins.
  • Low-molecular-weight materials are, for example, mineral oils, waxes or lubricating greases.
  • the present invention further relates, therefore, to the use of the compounds of formula (1 ) for the production of inks, for printing inks in printing processes, for flexographic printing, screen printing, the printing of packaging, security colour printing, intaglio printing or offset printing, for preliminary printing stages and for textile printing, for office and home use or for graphics, such as, for example, for paper goods, for ball-point pens, felt-tip pens, fibre-tip pens, paperboard, wood, (wood) stains, metal, stamp pads or inks for impact printing processes (with impact printing ink ribbons), for the production of colourants, for paints, for use in industry or advertising, for textile decoration and industrial labelling, for roll coating or powder coating compositions or for automobile paints, for high-solids (low-solvent), water-containing or metallic paints or for pigmented formulations for aqueous paints, for mineral oils, lubricating greases or waxes, for the production of coloured plastics for coatings, fibres, plates or moulded substrates
  • the present invention further relates to inks comprising high-molecular-weight organic material and a colour-producing amount of the compound of formula (1).
  • the inks can be produced by mixing the compounds according to the invention with polymeric dispersants.
  • the mixing of the compounds according to the invention with the polymeric dispersant is preferably carried out by generally known mixing methods, such as stirring or mixing, and the use of an intensive mixer, such as an Ultraturax, is especially to be recommended.
  • the weight ratio of the compounds according to the invention to ink is advantageously selected to be in the range of from 0.0001 to 75 % by weight, preferably from 0.001 to 50 % by weight, based on the total weight of the ink.
  • the present invention therefore relates also to a process for the production of inks which comprises mixing high-molecular-weight organic material with a colour-producing amount of the compound of formula (1).
  • the present invention further relates to colourants comprising high-molecular-weight organic material and a compound according to the invention of formula (1) in a colour-producing amount.
  • the present invention relates, in addition, to a process for the preparation of colourants which comprises mixing a high-molecular-weight organic material and a colour-producing amount of the compound according to the invention of formula (1).
  • the present invention further relates to coloured or pigmented plastics or polymeric coloured particles comprising high-molecular-weight organic material and compound of formula (1) in a colour-producing amount.
  • the present invention relates, in addition, to a process for the preparation of coloured or pigmented plastics or polymeric coloured particles which comprises mixing together a high-molecular-weight organic material and a colour-producing amount of the compound of formula ( D-).
  • the colouring of high-molecular-weight organic substances with the colourants of formula (1) is carried out, for example, by mixing such a colourant, optionally in the form of a master batch, into those substrates using roll mills or mixing or grinding apparatus, whereby the colourant is dissolved or finely distributed in the high-molecular-weight material.
  • the high-molecular-weight organic material with the admixed colourant is then processed according to procedures known perse, such as, for example, calendering, compression moulding, extrusion moulding, coating, spinning, casting or injection-moulding, whereby the coloured material acquires its final form.
  • Admixing of the colourant can also be carried out immediately prior to the actual processing step, for example by continuously metering a powdered colourant according to the invention and a granulated high-molecular-weight organic material, and optionally also additional ingredients, such as additives, directly into the inlet zone of an extruder simultaneously, where mixing takes place just before the processing operation. In general, however, prior mixing of the colourant into the high-molecular-weight organic material is preferred, since more uniform results can be obtained.
  • plasticisers it is often desirable for the purpose of producing non-rigid mouldings or reducing the brittle- ness thereof to incorporate so-called plasticisers into the high-molecular-weight compounds before shaping.
  • plasticisers for example, esters of phosphoric acid, phthalic acid or sebacic acid.
  • the plasticisers can be incorporated into the polymers before or after the incorporation of the colourant.
  • any desired amounts of constituents such as white, coloured or black pigments.
  • the high-molecular-weight organic materials and the compounds of formula (1) optionally together with additional ingredients, such as fillers, dyes, pigments, siccatives or plasticisers, are finely dispersed or dissolved in a common organic solvent or solvent mixture. That procedure may comprise dispersing or dissolving each individual component on its own or dispersing or dissolving several components together and only then combining all the components. Processing is carried out in accordance with customary methods, for example by spraying, film-spreading or one of the many printing methods, whereupon the paint or printing ink is advantageously cured thermally or by irradiation, optionally after previous drying.
  • the high-molecular-weight material to be coloured is a paint
  • it may be a conventional paint or a special paint, for example an automobile finish, preferably a metal-effect finish con- taining, for example, metal or mica particles.
  • thermoplastics especially also in the form of fibres, and printing inks.
  • Preferred high-molecular-weight organic materials that can be coloured according to the invention are, very generally, polymers having a dielectric constant > 2.5, especially polyesters, polycarbonate (PC), polystyrene (PS), polymethylmethacrylate (PMMA), polyamide, polyethylene, polypropylene, styrene/acrylonitrile (SAN) or acrylonitrile/butadie- ne/styrene (ABS). More especially preferred are polyesters, polycarbonate, polystyrene and PMMA.
  • polyesters especially preferred are polyesters, polycarbonate and PMMA, especially aromatic polyesters that can be obtained by polycondensation of terephthalic acid, such as, for example, polyethylene terephthalate (PET) or polybutylene terephthalate.
  • PET polyethylene terephthalate
  • PMMA polybutylene terephthalate
  • They can be used in the form of their monomers or copolymers or in the polymerised state in dissolved form as film formers or binders for paints that can be used for the decoration of metal or for decorative colour finishes, and for printing inks used, for example, in the ink-jet printing process, or also for wood stains.
  • the present invention also relates to mineral oils, lubricating greases and waxes comprising high-molecular-weight organic material and a compound of formula (1), in a colour-producing amount.
  • the present invention also relates to a process for the preparation of mineral oils, lubricating greases and waxes, which comprises mixing high-molecular-weight organic material with a colour-producing amount rf the compound of formula (1).
  • the present invention also relates to non-impact printing material comprising high-molecular- weight organic material and a compound of formula (1 ), in a colour-producing amount.
  • the present invention relates, in addition, to a process for the preparation of non-impact printing material, which comprises mixing together a high-molecular-weight organic material and a colour-producing amount of the compound of formula (1).
  • the present invention further relates to a process for the production of colour filters comprising a transparent substrate and a red, a blue and a green coating applied thereto in any de- sired sequence, which comprises using for the production of the red, blue and green coatings a correspondingly coloured compound of formula (1).
  • the different-coloured coatings are preferably arranged in such a pattern that they do not overlap over at least 5 % of their respective surface area and, most preferably, do not overlap at all.
  • the colour filters can be coated, for example, using inks, especially printing inks, comprising the compounds according to the invention, or, for example, by mixing a compound according to the invention with a chemically, thermally or photolyticaily structurable high-molecular- weight material (resist).
  • the further production can be carried out, for example, analogously to EP-A-654711, by application to a substrate, such as an LCD, subsequent photo-structuring and developing.
  • the invention further includes a transparent substrate coated with a red, a blue and a green coating each of a correspondingly coloured compound of formula (1), comprising pigmented high-molecular-weight organic material.
  • the sequence in which coating is carried out is not important as a rule.
  • the different-coloured coatings are preferably arranged in such a pattern that they do not overlap over at least 5% of their respective surface area and, most preferably, do not overlap at all.
  • the present invention also includes colour filters comprising a transparent substrate and, applied thereto, a red, a blue and a green coating, each obtainable from a correspondingly coloured compound of formula (1 ).
  • the present invention also includes the use of compounds of formula (1) for optical information storage applications (ois).
  • the present invention relates, in addition, to toners comprising high-molecular-weight organic material and a compound of formula (1), in a colour-producing amount.
  • the present invention also relates to a process for the production of toners, which comprises mixing together a high-molecular-weight organic material and a colour-producing amount of
  • the present invention also relates to inks or colourants for paints, printing inks, mineral oils, lubricating greases or waxes, or coloured or pigmented plastics, non-impact printing material, colour filters, cosmetics or toners comprising high-molecular-weight organic material and a compound of formula (1), in a colour-producing amount.
  • toners, paints, inks or coloured plastics are produced by processing master batches of toners, paints, inks or coloured plastics in roll mills or mixing or grinding apparatus.
  • a colour-producing amount of the compound of formula (1) means in the present invention normally from 0.0001 to 99.99 % by weight, preferably from 0.001 to 50 % by weight and especially from 0.01 to 50 % by weight, based on the total weight of the material coloured or pigmented therewith.
  • the coloured/pigmented high-molecular-weight materials obtained are distinguished by very high colour intensity, high saturation, good fastness to overspraying, good migration-stability, good fastness to heat, light and weathering and by a high gloss and good IR reflectance behaviour.
  • UV absorbers are advantageously mixed into the plastics or polymeric particles to be coloured with the compound of formula (1) according to the invention.
  • the amount of UV absorber can vary within a wide range; advantageously there is used from 0.01 to 1.0 % by weight, especially from 0.05 to 0.6 % by weight, more especially from 0.1 to 0.4 % by weight, of a UV absorber, based on the weight of the plastics or polymeric particles.
  • Example 1 (General method for condensation)
  • Example 8 (General Procedure for conversion of lactone to lactum) A suspended solution of 5-phenyl-3-(3-nitro) benzylidine-lactone from E ⁇ xample 1 (8.0 g, 0.027 mol) in absolute alcohol (60 ml) and ammonia solution (ca. 30%, d 0.89)(5 ml) is heated to 70-80° C for 15 minutes. Remaining ammonia solution (5 ml) and potassium carbonate (2.5 g) is added to it. The reaction is continued for 2 hours at 75-80° C maintaining the ammonia level in the solution by adding ammonia solution (ca. 10 ml), followed by the addition of potassium carbonate (ca. 2.5 g).
  • Example 30 Similar procedure is followed to prepare Example 30 (see Table 4) but using triethylamine instead of glacial acetic acid to neutralize 3-iminoisoindol-1-one.hydrochloride. Table 4
  • a stirred solution of hippuric acid (30 g, 0.16 mol), 1 -naphthalene (23.5 g, 0.16 mol) and sodium acetate (14 g, 0.17 mol) in acetic anhydride (250 ml) is heated under nitrogen atmosphere at 90-95° C for 2 hours.
  • the solution is cooled to 20° C, the curde product is filtered, and washed with acetic acid and water. Yield 24.5 g (49%) m. p.
  • polyester granules (PET Arnite D04-300, DSM) are pre-dried for 4 hours at
  • the resulting greenish yellow-coloured polyester granules have good allround fastness properties, especially good light fastness and high-temperature light fastness properties.
  • polyamide-6 granules Ultramid B3K, BASF are pre-dried for 4 hours at 75°C and then mixed homogeneously with
  • the homogeneous mixture is extruded in an extruder (twin screw 25 mm from Collin,
  • the resulting orange-coloured polyamide granules have good allround fastness properties, especially good light fastness and high-temperature light fastness properties.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Furan Compounds (AREA)
  • Ink Jet Recording Methods And Recording Media Thereof (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyrrole Compounds (AREA)
  • Cosmetics (AREA)
  • Paints Or Removers (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Thermal Transfer Or Thermal Recording In General (AREA)

Abstract

La présente invention a trait à des composés de formule (I), dans laquelle : R1 est hydrogène, hydroxy, halogène, nitro, cyano, amino, carboxy, ester carboxylique, sulfo, ester sulfonique, amide carboxylique, amide sulfonique, alcoxy, aryloxy, alkylthio ou arylthio ; X est -O-, -S-, -NH- ou -N(alkyle)- ; Y est hydrogène, ester carboxylique ; Z est =C ou =N- ; T est =C- ou =N- ; R2 est hydrogène, alkyle ou CN ; n est 0 ou 1, lorsque Z est =N- alors n est 0 ; m est 0 ou 1, lorsque T est =N- alors m est 0 ; A est un groupe aromatique hétérocyclique ou linéaire ou polycondensé qui est non substitué ou substitué par hydroxy alkyle, halogène, nitro, cyano, amino, acylamino, ester carboxylique, ester sulfonique, amide carboxylique, amide sulfonique, alcoxy, aryloxy, alkylthio, arylthio ou phényle, ou A ensemble avec T et R2 peuvent former un noyau allycylique ou hétérocyclique. L'invention a également trait à leur préparation et leur utilisation dans la production de matière plastique colorée ou de particules de polymère colorées.
EP04718971A 2003-03-19 2004-03-10 Nouveaux composes, leur procede de preparation et leur utilisation en tant que colorants et pigments Withdrawn EP1606249A2 (fr)

Applications Claiming Priority (3)

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IN229CH2003 2003-03-19
INMA02292003 2003-03-19
PCT/EP2004/050275 WO2004083170A2 (fr) 2003-03-19 2004-03-10 Nouveaux composes, leur procede de preparation et leur utilisation en tant que colorants et pigments

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EP1606249A2 true EP1606249A2 (fr) 2005-12-21

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EP (1) EP1606249A2 (fr)
JP (1) JP2006524728A (fr)
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JP5224785B2 (ja) * 2006-11-08 2013-07-03 富士フイルム株式会社 有機顔料ナノ粒子の製造方法
JP2010267612A (ja) 2009-04-17 2010-11-25 Konica Minolta Business Technologies Inc 光電変換素子及び太陽電池
JP5878356B2 (ja) * 2011-09-30 2016-03-08 富士フイルム株式会社 着色組成物、および画像表示構造
JP6162984B2 (ja) * 2013-03-14 2017-07-12 山本化成株式会社 感熱発色性組成物及び該組成物を用いてなる感熱記録材料
WO2020120540A1 (fr) * 2018-12-13 2020-06-18 Essilor International Lentille ophtalmique comprenant un oxazolone

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DE2658942A1 (de) * 1976-12-24 1978-07-06 Basf Ag Chiral substituierte 2-imidazolin- 5-one
WO2003010135A1 (fr) * 2001-07-26 2003-02-06 Ajinomoto Co., Inc. Nouveaux derives de l'acide phenylpropionique
JP4164633B2 (ja) * 2001-11-30 2008-10-15 山田化学工業株式会社 ピロール化合物
FR2833164B1 (fr) * 2001-12-07 2004-07-16 Oreal Compositions cosmetiques antisolaires a base d'un melange synergique de filtres et utilisations

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See references of WO2004083170A2 *

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WO2004083170A2 (fr) 2004-09-30
JP2006524728A (ja) 2006-11-02
WO2004083170A3 (fr) 2005-04-28
CA2518707A1 (fr) 2004-09-30

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