EP1603902A1 - Neue heterocyclische verbindungen, verfahren zu deren herstellung und deren verwendung als farbstoffe und pigmente - Google Patents

Neue heterocyclische verbindungen, verfahren zu deren herstellung und deren verwendung als farbstoffe und pigmente

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Publication number
EP1603902A1
EP1603902A1 EP04741425A EP04741425A EP1603902A1 EP 1603902 A1 EP1603902 A1 EP 1603902A1 EP 04741425 A EP04741425 A EP 04741425A EP 04741425 A EP04741425 A EP 04741425A EP 1603902 A1 EP1603902 A1 EP 1603902A1
Authority
EP
European Patent Office
Prior art keywords
formula
hydrogen
printing
compound
mol
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Withdrawn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
EP04741425A
Other languages
English (en)
French (fr)
Inventor
Jean-Marie Adam
Pramod V. Dalvi
Vadiraj Subbanna Ekkundi
Jean-Pierre Bacher
Ramaswami Wilderness Society SREENIVASAN
Deepak M. Hsg. Society RANE
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 EP1603902A1 publication Critical patent/EP1603902A1/de
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/44—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/96—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three 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
    • C07D263/36—One oxygen atom
    • C07D263/40—One oxygen atom attached in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members

Definitions

  • the present invention relates to new compounds, to their preparation and to their use in the production of coloured plastics or polymeric colour particles
  • R-i is hydrogen, hydroxy, halogen, nitro, cyano, ammo, carboxy, carboxylic ester, sulfo, sulfonic ester, carboxylic amide, sulfonic amide, alkylthio, arylthio, alkoxy or aryloxy
  • R' ⁇ is hydrogen, hydroxy, halogen, nitro, cyano, ammo, carboxy, carboxylic ester, sulfo, sulfonic ester, carboxylic amide, sulfonic amide, alkylthio, arylthio, alkoxy or aryloxy
  • X is -0-, -S-, -NH- or -N(alkyl)-
  • X' is -0-, -S-, -NH- or -N(alkyl)-
  • Y is hydrogen or carboxylic ester
  • Y' is hydrogen or carboxylic ester
  • Z ⁇ s C-
  • n 0, 1 , 2 or 3
  • m 0, 1 , 2 or 3
  • B is a phenyl ring
  • W is a heterocyclic, or linear or polycondensed aromatic group which is unsubstituted or substituted by alkyl, halogen, hydroxy, alkoxy, alkylthio or amino
  • R 2 is hydrogen, alkyl, halogen, hydroxy, alkoxy, alkylthio or amino.
  • an alkyl is for example a straight-chain or branched C ⁇ alkyl as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, 2-pentyl, 3-pentyl, 2,2-dimethylpropyl, hexyl, heptyl, 2,4,4-trimethylpentyl, 2-ethylhexyl or octyl, preference being given to a C 1-4 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 1-8 alkoxy, for example methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert. butoxy, n-pentyloxy, 2-pentyloxy, 3-pentyloxy, 2,2-dimethylpropoxy, n-hexyloxy, n-heptyloxy, n-octyloxy, 1 ,1 ,3,3-tetramethylbutoxy or 2-ethylhexyloxy.
  • an aryloxy is to be understood as being for example a C 6 . 24 aryl- oxy, preferably a C 6- ⁇ 2 aryloxy radical, for example phenoxy or 4-methylphenoxy.
  • an arylthio is for example phenylthio or napthylthio.
  • W as aromatic group includes, for example, phenylene, naphthalene, acenaphthylene, anthracene, phenanthrene, naphthacene, chrysene, pyrene or perylene.
  • W is preferably phenylene, naphthalene, anthracene, phenanthrene, perylene or pyrene, and most preferably phenylene or naphthalene.
  • W as heterocyclic group is, for instance, pyhdine, pyrazine, pyrimidine, pyridazine, indole iso- indole, quinoline, isoquinoline, carbazole, phenothiazine, benzimidazolone, benzothiazole, pyrrolo, imidazole, pyrrolidine, piperidine, piperazine, morpholine or pyrazole.
  • an ester is for example methyl-, ethyl-, propyl- or butylester.
  • preferred compounds of formula (1 ) are a) compounds of phenyl-butyrolactams of formula
  • preferred compounds of formula (1 ) are e) compounds of phenyl-carboethoxy-butyrolactams of formula
  • n 0, 1 or 2
  • the compounds of formula (1 ) according to the invention are prepared, for example, by reacting 2 mol of compound of formula
  • R 1 , R ⁇ , X, X , Y, Y , Z, Z, x and y are as defined above for formula (1), n is 0, 1 , 2 or 3, m is 0, 1 , 2 or 3, B is a phenyl ring, R 2 is hydrogen, alkyl, halogen, hydroxy, alkoxy, alkylthio or amino and R 3 is hydrogen, C C 12 alkyl or CN, at elevated temperature or by oxidation 2 mol of compound of formula (50) at elevated temperature or by oxidation 1 mol of compound of formula (50) and 1 mol of compound of formula (51 ) at elevated temperature.
  • Ph means phenyl and Ac 2 0 means acetic anhydride
  • the compound of formula (1 ) can be symmetrical or asymmetrical and can contain one or more water soluble groups (sulfonic, carboxylic or cationic groups).
  • Water soluble derivatives of compounds of formula (1 ) 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; polycarbonates, for example those formed from ⁇ , ⁇ -dimethyl-4,4-dihydroxydiphenylmethane and phosgene; or fibres based on polyvinyl chloride or polyamide.
  • 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
  • polycarbonates for example those formed from ⁇ , ⁇ -dimethyl-4,4-dihydroxydiphenylmethane and phosgene
  • fibres based on polyvinyl chloride or polyamide are especially linear aromatic polyesters, for example polyesters formed from a terephthalic acid
  • 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 1 15°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. It is advantageous to convert the dyes into a dye preparation before use for this, 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. For example, 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 products, 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 tincto ally 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 5 -10 7 g/m°l. 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 polyfluoroethylene, polytrifluoro- chloroethylene or tetrafluoroethylene/hexafluoropropylene mixed polymerisate, and copoly- merisates of the mentioned monomers, especially ABS (acrylonitrile/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 or thiourea, 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, for
  • 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
  • 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 per se, 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.
  • additional ingredients such as additives
  • 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 containing, 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 of 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 desired 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 photolytically structurable high-molecular- weight material (resist).
  • the further production can be carried out, for example, analogously to EP-A-654 711 , 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 the compounds of formula (1 ) for optical infor- mation 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 compound of formula (1 ).
  • 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.
  • the following Examples serve to illustrate the invention Unless otherwise indicated, the parts are parts by weight and the percentages are percentages by weight The temperatures are given in degrees Celsius The relationship between parts by weight and parts by volume is the same as that between grams and cubic centimetres
  • Et means -CH 2 CH 3
  • Me means -CH 3
  • OMe means -OCH 3
  • t-But means -C(CH 3 ) 3
  • Ph means -Phenyl
  • OEt means -OCH 2 CH 3
  • n-But means -(CH 2 ) 3 CH 3
  • Table 1
  • Benzoylacrylic acid (10. Og, 0.056 mol), cuprous chloride (2.0 g, 0.010 mol), ammonium chloride (2.2 g, 0.041 mol) are taken in acetic anhydride (50 ml). It is gradually heated to reflux under stirring for 2 hours. After the reaction is over, it is thoroughly cooled in an ice bath. Settled solids are filtered through Buchner funnel. Solids are washed with acetic anhydride, water and ethanol to give the crude product (5.2 g). The crude solids are purified by soxhlet extraction in toluene to give pure red colored solids (3.8 g, 42%). m. p.315°C, Anal. Gale. For C 20 H 12 O 4 ; C, 75.94; H, 3.82; Found: C, 74.79; H, 3.82. All other compounds given in the Table 2 are obtained following the above same procedure.
  • 2,3-Bis-benzoylamino-succinic acid (5.0 g, 0.014 mol) (synthesized as given in Stachei, S. D. et al. Arch. Pharm. 312, 968, 1979) is taken in thionyl chloride (50 ml) and refluxed for 2 hours. Excess thionyl chloride is distilled off. Traces of thionyl chloride are removed by toluene co-distillation. It is cooled to room temperature and water is added to it. The crude mass is then filtered and dried in an oven till constant weight. The red colored pure product obtained, weighted (3.5g, 78%). Anal. Calc.
  • Benzamidine free base (6.0 g, 0.049 mol) and dimethyl acetylenedicarboxylate (3.6 g, 0.025 mol) are taken in benzene (ca. 50 ml).
  • the deep red colored solution obtained is heated to reflux for 2 hours.
  • the cooled mixture is filtered to give (9.0 g) of the crude.
  • the crude product is taken in minimum amount of warm DMF and poured on large excess of water under stirring.
  • the solids separated (2.1 g) are filtered and soxhlet extracted with methanol for 16 hours.
  • the methanol insoluble pure red colored product obtained, weighted (0.8 g, 10%).
  • 5-Phenyl-4-carbethoxy-1 ,3-dihydro-pyrrol-2-one (2.3 g, 0.01 mol) is dissolved in acetic acid (50 ml) at 60 to 70° C.
  • acetic acid 50 ml
  • 2,5-dimethoxy- terephthalaldehyde 1.0 g, 0.005 mol
  • temperature is increased to 100° C. Heating is continued for 3 hours and after cooling, solids are filtered through Buchner funnel.
  • the crude product is washed with acetic acid, water, DMF and methanol. Finally the crude product is dissolved in cone, sulphuric acid, reprecipitated from water and filtered.
  • 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)
  • Compositions Of Macromolecular Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Plural Heterocyclic Compounds (AREA)
EP04741425A 2003-03-19 2004-03-10 Neue heterocyclische verbindungen, verfahren zu deren herstellung und deren verwendung als farbstoffe und pigmente Withdrawn EP1603902A1 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
IN228CH2003 2003-03-19
INMA02282003 2003-03-19
PCT/EP2004/050276 WO2004089941A1 (en) 2003-03-19 2004-03-10 New heterocyclic compounds, a process for their preparation and their use as dyes and pigments

Publications (1)

Publication Number Publication Date
EP1603902A1 true EP1603902A1 (de) 2005-12-14

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RU2383539C2 (ru) * 2005-06-08 2010-03-10 Джапан Тобакко Инк. Гетероциклические соединения
JP2008106021A (ja) * 2006-10-27 2008-05-08 Dainippon Ink & Chem Inc ピロリノン化合物の製造方法及びビピロリノン化合物の製造方法
CN103664916B (zh) * 2012-09-12 2016-08-24 中国科学院化学研究所 基于联噻吩亚二吡咯及其衍生物的共轭小分子材料及其制备方法与应用
CN117715988A (zh) * 2022-07-15 2024-03-15 Dic株式会社 联吡咯啉酮化合物

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DE2608481C2 (de) * 1976-03-02 1978-03-30 Hoechst Ag, 6000 Frankfurt Verfahren zum Farben von wasserunlöslichen, thermoplastischen Polymerisaten und Polykondensaten in der Masse

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