WO1998012263A1 - Colorant azoique pour imprimante a jet d'encre - Google Patents

Colorant azoique pour imprimante a jet d'encre Download PDF

Info

Publication number
WO1998012263A1
WO1998012263A1 PCT/GB1997/002377 GB9702377W WO9812263A1 WO 1998012263 A1 WO1998012263 A1 WO 1998012263A1 GB 9702377 W GB9702377 W GB 9702377W WO 9812263 A1 WO9812263 A1 WO 9812263A1
Authority
WO
WIPO (PCT)
Prior art keywords
formula
nhc
alkyl
independently
alkoxy
Prior art date
Application number
PCT/GB1997/002377
Other languages
English (en)
Inventor
Christine Millard
Roy Bradbury
Peter Gregory
Original Assignee
Zeneca Limited
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
Priority claimed from GBGB9619612.6A external-priority patent/GB9619612D0/en
Priority claimed from GBGB9619585.4A external-priority patent/GB9619585D0/en
Priority claimed from GBGB9619591.2A external-priority patent/GB9619591D0/en
Priority claimed from GBGB9619586.2A external-priority patent/GB9619586D0/en
Priority claimed from GBGB9619589.6A external-priority patent/GB9619589D0/en
Priority claimed from GBGB9619572.2A external-priority patent/GB9619572D0/en
Priority claimed from GBGB9619592.0A external-priority patent/GB9619592D0/en
Priority claimed from GBGB9619593.8A external-priority patent/GB9619593D0/en
Priority claimed from GBGB9619571.4A external-priority patent/GB9619571D0/en
Priority claimed from GBGB9619574.8A external-priority patent/GB9619574D0/en
Priority claimed from GBGB9619588.8A external-priority patent/GB9619588D0/en
Priority claimed from GBGB9619575.5A external-priority patent/GB9619575D0/en
Priority claimed from GBGB9619570.6A external-priority patent/GB9619570D0/en
Priority claimed from GBGB9619587.0A external-priority patent/GB9619587D0/en
Priority claimed from GBGB9619590.4A external-priority patent/GB9619590D0/en
Priority claimed from GBGB9619584.7A external-priority patent/GB9619584D0/en
Priority to GB9902959A priority Critical patent/GB2332441B/en
Priority to US09/269,061 priority patent/US6290763B1/en
Priority to AU41260/97A priority patent/AU4126097A/en
Application filed by Zeneca Limited filed Critical Zeneca Limited
Publication of WO1998012263A1 publication Critical patent/WO1998012263A1/fr

Links

Classifications

    • 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
    • C09D11/00—Inks
    • C09D11/30—Inkjet printing inks
    • C09D11/32—Inkjet printing inks characterised by colouring agents
    • C09D11/328—Inkjet printing inks characterised by colouring agents characterised by dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B43/00—Preparation of azo dyes from other azo compounds
    • C09B43/12—Preparation of azo dyes from other azo compounds by acylation of amino groups
    • C09B43/136—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents
    • C09B43/16—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents linking amino-azo or cyanuric acid residues

Definitions

  • This invention relates to dyes, to inks and to their use in ink jet printing ("UP").
  • UP is a non-impact printing technique in which droplets of ink are ejected through a fine nozzle onto a substrate without bringing the nozzle into contact with the substrate.
  • the inks are often required to dry quickly when applied to a substrate to prevent smudging, but they should not form a crust over the tip of an ink jet nozzle because this will stop the printer from working.
  • the inks should also be stable to storage over time without decomposing or forming a precipitate which could block the fine nozzle.
  • Formula (1) which comprises any suitable form of the compound: such as salt; stereoisomer, zwitterion, polymorph, complex, isotopic form, combinations thereof in the same species and mixtures thereof; where: n represents from 1 to 5 inclusive; R ⁇ R 1B , R 4 and R 4B each independently comprises at least one of the following substituents, optionally substituted:
  • R 5 and R 6 each independently comprises at least one of the following substituents: H, C 1 . B alkyl and aryl; and R 2 and R 3 each independently comprises at least one of the following substituents, optionally substituted:
  • X comprises one of the following: -NHC.,- 8 alkylene;
  • X comprises one of the following: -NHC ⁇ alkylene
  • Formula (2) a moiety of Formula(2) where m and p is each independently from 0 to 5 inclusive, provided that (m + p) is from 1 to 5 inclusive, and R 1A , R 2A , R A and R 4C each independently comprises at least one of those optionally substituted substituents as defined herein for R 1 , R 2 , R 4 and R 4S respectively; and any other suitable labile or non-labile substituent not mentioned above, where the optional substituents herein comprise: C alkyl (optionally substituted with at least one halo) , C,. 4 alkoxy (optionally substituted with at least one halo), carboxy, sulpho hydroxy, ammo, mercapto, cyano, nitro and halo
  • R 2 and/or R 3 represent a labile atom or group, it is preferably an atom or group which is bound by a chemical bond to the t ⁇ azine nucleus which is displaceable by a hydroxyl group of cellulose under mildly alkaline aqueous conditions to form a covalent bond between the triazine nucleus and cellulose Labile atoms and groups that may be represented by R 2 and/or R 3 independently comprise: halo (preferably F and Cl), sulphonic acid groups; thiocyano groups; optionally substituted quaternary ammonium groups (preferably t ⁇ alkylammonium groups) and/or optionally substituted pyridinium groups (preferably 3- and 4-carboxy pyridinium groups)
  • Preferred non-labile groups represented by R 2 and/or R 3 independently comprise groups of the formulae -OR 7 , -SR 8 and/or -NR 9 R 10 , more preferably -OH,-NH 2 , -NH(C 1
  • R 7 , R 8 , R 9 and/or R 10 are each independently selected from the following optionally substituted substituents.
  • H alkyl (preferably C h alky!, especially C 1 . 4 alkyl); cycloalkyl, aryl (preferably phenyl), aralkyl [preferably -(CH 2 ) 1 .
  • R 9 and R 10 together with the nitrogen atom to which they are attached form an optionally substituted 5- or 6- membered ring, preferably an optionally substituted morpholine, piperidine or piperazine ring, more preferably piperazine in which the free ring N-atom is optionally substituted by a C ⁇ _ 4 -alkyl or hydroxy-C 2 . 4 -alkyl group
  • the substituent is preferably selected from the optional substituents listed above, more preferably is selected from: hydroxy, methyl, methoxy, sulpho and carboxy
  • Advantageous dyes of Formula (1) are those in which n ⁇ s 2,
  • R 1B and R 4B represent H;
  • R 1 represents H, or -NHCONR 5 R 6 ;
  • R 4 represents H, C. B alkyl or C,. 8 alkoxy; and R 2 and R 3 each independently represents H, C- 8 alkoxy, -NHC, 8 alkyleneOH, -SC, 8 -alkyleneSO 3 H, -NHC, 8 alkyleneN(C. 8 alkyl) 2 ,
  • any radical group mentioned above as a substituent refers to a monovalent radical unless otherwise stated
  • a group which comprises a chain of three or more atoms signifies a group in which the chain wholly or in part may be linear, branched and/or form a ring (including spiro and/or fused rings)
  • the total number of certain atoms is specified for certain substituents for example C ⁇ n alkyl, signifies an alkyl group comprising from 1 to n carbon atoms
  • the substituent may replace any H attached to an atom in the ring and may be located at any available position on the ring
  • Hydrocarbon substituents or parts of substituents may comprise one or more double and/or triple carbon to carbon bonds and the term 'alkyl' as used herein encompasses alkenyl and alkynyl
  • the term 'aryl' encompasses alkenyl and alkynyl
  • 'aryl' encompasses alkenyl and alkynyl
  • composition ingredients, substituents and/or compounds described herein will be understood to mean suitable for use in UP for example by providing desirable properties to the ink or being compatible with any inert carriers and/or diluents suitable for formulating such inks
  • suitable compounds are those which will, in addition, undergo the specified reactions To be particularly acceptable for use in UP compounds of Formula (1 ) may be Ames negative
  • At least one mono azo dye of Formula (1) including any suitable salts and tautomers thereof, in which n is 2, R 1B , R 4 and R 4B are all H,
  • R 1 is H, or -NHCONR 5 R 6 , where R 5 and R 6 is each independently H, C, 4 alkyl or aryl, and R 2 and R 3 is each independently -NHC 1 4 alkyleneOH, -SC. ⁇ alkyleneSOaH,
  • More preferred monoazo dyes of Formula (1) in this first preferred aspect of the invention are those in which: the carboxy groups on the phenyl ring in Formula (1) are meta to the azo group; and R 1 is methyl or NHCOCH 3
  • at least one bisazo dye of Formula (1) including any suitable salts and tautomers thereof, in which: n is 2; R 1B and R 4B are both H;
  • R and R A is each independently: H, C 1 . 4 alkoxy, NHCOH, C 1 . 4 alkylcarbonylamino, or NHCONR 5 R 6 ; where R s and R 6 is each independently H, C 1 - alkyl or aryl; R 4 and R 4A is each independently H, C ⁇ alkyl or -C 4 alkoxy; R 2 is a moiety of Formula (2) where m is 2, p is 0 and R 4C is H; R 2A is H, or C-. 4 alkoxy; and R 3 is: -NHC ⁇ alkyleneOH, -SC ⁇ alkyleneSOaH, -NHC 1 . 4 alkyleneN(C 1 . 4 -alkyl) 2 ;
  • R 5 and R 6 is each independently H, C.. 4 alkyl or aryl; and R 2 and R 3 is each independently: -NHC 1 . 4 alkyleneOH, -SC 1 . 4 alkyleneSO 3 H,
  • More preferred monoazo dyes of Formula (1) in this third preferred aspect of the invention are those in which: the carboxy groups on the phenyl ring in Formula (1) are meta to the azo group; R 1 is methyl, -NHCOCH 3 ; -NHCONH 2 ; or methoxy; and R 4 is methoxy.
  • at least one bisazo dye of Formula (1) (which comprises at least one piperazinyl substituent), including any suitable salts and tautomers thereof, in which
  • R 1B and R 4B are both H
  • R 1 and R 1A is each independently H, C 1 4 alkyl, C 1 4 alkoxy, -NHCOH, C- 4 alkylcarbonylam ⁇ no or NHCONR 5 R 6 where R 5 and R 6 is each independently H, C, 4 -alkyl or aryl, R" and R 4A is each independently H, C- 4 alkyl or C, 4 alkoxy, R 2 is a moiety of Formula (2) where m is 2, p is 0 and R 4C is H, R 2A is H, and
  • R 3 is ' where X is -NHC, 4 alkylene or a direct link
  • More preferred bisazo dyes of Formula (1) in this fourth preferred aspect of the invention are those in which the carboxy groups on the phenyl rings in Formulae (1) and (2) are meta to the azo group, R 1 and R 1A is each independently methoxy, -NHCOCH 3 or -NHCONH 2 , and R 4 and R 4A is each independently H or methoxy
  • Salts of Formula (1) may be formed from one or more organic and/or inorganic base(s) or ac ⁇ d(s) and compounds of Formula (1 ) which are acidic and/or basic (for example acid and/or base addition salts)
  • Salts of Formula (1) comprise all acceptable salts that may be formed from monovalent and/or multivalent acids and/or bases [for example those formed by partial neutralisation of carboxy lie acids of Formula (1) where n + m > 1]
  • Salts of Formula (1) also comprise all enantiome ⁇ c salts formed with acceptable chiral acids and/or bases and/or any mixtures of enantiomers of such salts (for example racemic mixtures)
  • Preferred salts are alkali metal salts, especially lithium, sodium and potassium salts, ammonium and substituted ammonium salts
  • Especially preferred salts are salts with ammonia and volatile amines
  • the dyes may be converted into a salt using known techniques For example, an alkali metal salt of a
  • Certain compounds of Formula (1 ) may exist as one or more stereoisomers, for example, enantiomers diastereoisomers, geometric isomers, tautomers, conformers and/or suitable combinations thereof possible in the same species It is particularly preferred that dyes of Formula (1 ) comprise all tautome ⁇ c forms including those not specifically illustrated herein
  • the present invention comprises all acceptable stereoisomers of compounds of Formula (1) and any suitable mixtures thereof
  • Certain compounds of Formula (1) may exist as one or more zwittenons, for example, species which comprise two or more centres of ionic charge
  • the present invention comprises all acceptable zwittenons of Formula (1) and any suitable mixtures thereof
  • Certain compounds of Formula (1) may exist as one or more polymorphs, for example, phases, crystalline forms, amorphous forms, solid solutions, interstitial compounds and/or any suitable mixtures thereof
  • the present invention includes all acceptable polymorphs of Formula (1) and any suitable mixtures thereof
  • Certain compounds of Formula (1) may exist in the form of one or more complexes, for example, chelates, solvates, organometallic complexes, and/or complexes with other suitable ligands Such complexes may be formed between an acceptable substrate in which the compound of Formula (1 ) and/or the substrate may act as a ligand
  • the substrate may comprise one or more acceptable solvents to form solvates
  • the complexes may be non-stoichiomet ⁇ c, for example if the complex is a hydrate it may comprise a hemihydrate, monohydrate and/or dihydrate
  • the present invention includes all acceptable complexes of Formula (1) and any suitable mixtures thereof
  • Certain compounds of Formula (1) may exist as one or more isotopic forms in which one or more atoms in Formula (1 ) comprise one or more suitable isotopes
  • the natural ratios of various isotopes may be altered by suitable means, for example certain 12 C atoms in certain compounds of Formula (1) may be substantially replaced by the less common 1 C and/or
  • Compounds of Formula (1) in which R 2 is a moiety of Formula (2) may be prepared by condensing a suitable compound of Formula (1) in which R 3 is Cl with a compound of formula R 3 H in which R 3 is other than Cl.
  • Compounds of Formula (1) in which R 2 is a moiety of Formula (2) and R 3 is Cl may be prepared by condensing a suitable compound of Formula (3) preferably in the presence of a base with a suitable compound of Formula (4):
  • Compounds of Formula (3) may be prepared by condensing with cyanuric chloride, preferably tn the presence of a base, a suitable azo compound of Formula (5):
  • Compounds of Formula (4) may be prepared by diazotising a suitable aromatic amine of Formula (6):
  • diazotisation is preferably performed at a temperature below 6°C, more preferably at a temperature in the range -10°C to 5°C
  • diazotisation is performed in water, more preferably at a pH below 7
  • Dilute mineral acids such as HCI or H 2 SO 4 , are often used to achieve the desired acidic conditions
  • the azo dyes may be isolated by known methods such as spray drying or precipitation followed by filtration
  • An aspect of the present invention comprises an ink comprising at least one compound of Formula (1) as defined herein and a suitable medium
  • an ink comprising
  • the number of parts of component (a) is preferably from 0 1 to 20, more preferably from 0 5 to 15, and especially from 1 to 5 parts
  • the number of parts of component (b) is preferably from 99 9 to 80, more preferably from 99 5 to 85, especially from 99 to 95 parts
  • component (a) is completely dissolved in component (b)
  • component (a) has a solubility in component (b) at
  • Preferred liquid media include water, a mixture of water and an organic solvent and an organic solvent free from water
  • the weight ratio of water to organic solvent is preferably from 99 1 to 1 99 more preferably from 99 1 to 50 50 and especially from 95 5 to 80 20
  • the organic solvent comprising the mixture of water and organic solvent is a water-miscible organic solvent or a mixture of such solvents
  • the liquid medium may comprise water and preferably two or more, more preferably from 2 to 8, water-soluble organic solvents
  • Preferred water-miscible organic solvents comprise C- 6 -alkanols, preferably methanol, ethanol, n-propanol, isopropanol, n-butanol, sec-butanol, tert-butanol, n-pentanol, cyclopentanol and/or cyclohexanol, linear amides, preferably dimethylformamide and/or dimethylacetamide, ketones and/or ketone-alcohols, preferably acetone, methyl ether ketone,
  • C- ⁇ alkyl ethers of diols preferably monoC ⁇ alkyl ethers of C 2 12 d ⁇ ols ⁇ for example 2-methoxyethanol, 2-(2-methoxyethoxy)ethanol, 2-(2-ethoxyethoxy)-ethanol,
  • More preferred water-soluble organic solvents are selected from cyclic amides (e g 2-pyrrol ⁇ done, N-methyl-pyrrolidone and N-ethyl-pyrro done), diols, (e g 1,5-pentane diol, ethyleneglycol, thiodiglycol, diethyleneglycol and tnethyleneglycol), C ⁇ alkyl ethers of diols (e g 2-methoxy-2-ethoxy-2-ethoxyethanol), and any suitable mixtures thereof
  • a preferred liquid medium comprises
  • Another preferred liquid medium comprises (a) from 60 to 80 parts water, (b) from 2 to 20 parts diethylene glycol, and
  • suitable media for inks of the present invention comprise a mixture of water and one or more organic solvents are described in US 4,963,189, US 4,703,113, US 4,626,284 and EP 0425150-A.
  • the solvent preferably has a boiling point of from 30° to 200°C, more preferably of from 40° to 150°C, especially from 50 to 125°C.
  • the organic solvent may be water-immiscible, water-miscible or a mixture of such solvents.
  • Preferred water- miscible organic solvents comprise any of those described above and mixtures thereof.
  • Preferred water-immiscible solvents comprise aliphatic hydrocarbons; esters (for example ethyl acetate) chlorinated hydrocarbons (for example dichloromethane), ethers (for example diethyl ether) and mixtures thereof.
  • the liquid medium comprises a water-immiscible organic solvent
  • a polar solvent for example a C,. 4 alkanol
  • the liquid medium is an organic solvent free from water it comprises a ketone (especially methyl ethyl ketone) and/or an alcohol (especially a C ⁇ alkanol, more especially ethanol or propanol).
  • the organic solvent free from water may be a single organic solvent or a mixture of two or more organic solvents. It is preferred that when the medium is an organic solvent free from water it is a mixture of 2 to 5 different organic solvents. This allows a medium to be selected which gives good control over the drying characteristics and storage stability of the ink.
  • Ink media comprising an organic solvent free from water are particularly useful where fast drying times are required and particularly when printing onto hydrophobic and non-absorbent substrates, for example plastics, metal and glass.
  • Preferred low melting solid media have a melting point in the range from 60°C to
  • Suitable low melting point solids include long chain fatty acids or alcohols, preferably those with C 18 . 24 chains, and sulphonamides.
  • the dye of Formula (1) may be dissolved in the low melting point solid or may be finely dispersed in it.
  • the ink may also contain additional components conventionally used in inks for P, for example viscosity and surface tension modifiers, corrosion inhibitors, biocides, kogation reducing additives and surfactants which may be ionic or non-ionic.
  • additional components conventionally used in inks for P for example viscosity and surface tension modifiers, corrosion inhibitors, biocides, kogation reducing additives and surfactants which may be ionic or non-ionic.
  • a further aspect of the invention provides a process for printing an image on a substrate comprising applying an ink comprising a dye of Formula (1) to the substrate by means of an ink jet printer.
  • the ink used in this process is preferably an ink of the present invention as defined herein.
  • the ink jet printer preferably applies the ink to the substrate in the form of droplets which are ejected through a small orifice onto the substrate.
  • Preferred ink jet printers are piezoelectric ink jet printers and thermal ink jet printers.
  • thermal ink jet printers programmed pulses of heat are applied to the ink in a reservoir by means of a resistor adjacent to the orifice, thereby causing the ink to be ejected in the form of small droplets directed towards the substrate du ⁇ ng relative movement between the substrate and the orifice
  • piezoelectric ink jet printers the oscillation of a small crystal causes ejection of the ink from the orifice
  • Preferred textile materials are natural, synthetic and semi-synthetic materials
  • preferred natural textile materials include wool, silk, hair and cellulosic materials, particularly cotton, jute, hemp, flax and linen
  • preferred synthetic and semi-synthetic materials include polyamides, polyesters, polyacrylonit ⁇ les and polyurethanes
  • the textile material has been treated with an aqueous pre-treatment composition comprising a thickening agent and optionally a water-soluble base and a hydrotropic agent and dried prior to step i) above
  • an aqueous pre-treatment composition comprising a thickening agent and optionally a water-soluble base and a hydrotropic agent and dried prior to step i) above
  • the pre-treatment composition preferably comprises a solution of the base and the hydrotropic agent in water containing the thickening agent
  • Particularly preferred pre- treatment compositions are described more fully in EP 0534660-A
  • the invention is further illustrated by the following Examples in which all parts and percentages are by weight unless otherwise stated
  • 3-Mercapto-1 -propane sulphonic acid (4 8 g) was dissolved in water (100 cm 3 ) and added to the mixture which was then stirred at pH 8 0 and room temperature for 16 hours A further portion of 3-mercapto-1 -propane sulphonic acid (13 5 g) in water (100 cm 3 ) was added to the mixture which was warmed to 50° C and kept at pH 8 to 9 for 6 hours and then was cooled to room temperature
  • Morpholine (3.6g) was added to the mixture which was then stirred at pH 8 to 9 and room temperature for 16 hours.
  • 2,5-Dimethoxyaniline (23 g) was dissolved with stirring in warmed ethanol (300 m 3 ) and the solution was cooled and added slowly to diazo solution prepared above. The mixture was stirred for 16 hours. A solid was collected by filtration under reduced 5 pressure and was dried in an oven at 60° C for 16 hours.
  • Example 6 The procedure of Example 6 was repeated except that at stage iii) morpholine (13.2 g) was used in place of the 3-mercapto-1-propanesulphonic acid to give the title compound (15.0 g).
  • Morpholine (18g) was added and the mixture was stirred at 65 to 75° C for 60 hours and then was cooled to room temperature.
  • This compound was prepared as described for Example 9 except that 3-mercapto-1- propanesulphonic acid (36 g) was used in place of the morpholine.
  • N-Acetylsulphanilyl chloride (116.5 g) was added to water (600 ml) at room temperature and the mixture was stirred
  • 2-Chloroethylam ⁇ ne hydrogen chloride (87 g) was dissolved in water (200 ml) and this solution was added to the sulphanilyl chloride mixture formed above.
  • the pH of the mixture was adjusted to pH 7 0 to 7.5 with a 15% solution of sodium carbonate and the mixture was stirred overnight at room temperature
  • the precipitate formed was collected by filtration under reduced pressure and then wasted with water (2 I) to give a damp paste
  • the paste was stirred into 2 N HCI (1 I) at a temperature of 80 to 85° C for 3 hours, until TLC showed the hydrolysis was complete
  • the solution was cooled to 0 to 10° C and the pH of the mixture was adjusted to pH 8 5 by adding solid sodium carbonate, whilst the temperature of the mixture was kept below 10° C
  • a solid was collected by filtration under reduced pressure, washed with water (3 I) and dried in an oven at 70° C to give 58.5 g of product
  • Piperazine (20g) was added and the mixture was warmed slowly to 70° C for 4 hours and then was cooled to room temperature.
  • the mixture was neutralised to pH 7 with concentrated HCI to form a precipitate which was collected by filtration under reduced pressure
  • the solid product was added to water (400 cm 3 ) to form a slurry the pH of which was adjusted to 9 with ammonia solution
  • the slurry was poured onto concentrated HCI (30 cm 3 ) and stirred for 10 minutes A solid was collected from the slurry by filtration under reduced pressure.
  • This compound was prepared as described for Example 15 (i) except that the equivalent molar amount of aniline was used in place of the o-anisidine.
  • 5-Aminoisophthalic acid (36.2 g) was dissolved in water (1 I) with stirring and the pH was adjusted to 8.0 with NaOH solution, then sodium nitrite (14 g) was added. The resulting solution was poured onto a mixture of concentrated HCI (60 cm 3 ) in ice (100 g) at a temperature of between 0 to10° C and stirred for 2 hours also at 0 to 10°C Excess nitrite was removed with a 10% solution of sulphamic acid
  • Ethanolamine (9.2 g, 6M) was added and the mixture was warmed to 70 ⁇ 5° C for 6 hours and then was cooled to room temperature.
  • the exemplified compounds 1 to 19, prepared as described above, were converted to their purified ammonium salts as follows. Each example was stirred in ammonia solution and a solid was collected by filtration. The crude ammonium salt thus obtained was then re-dissolved in ammonia solution the pH of which was adjusted to 9.
  • the solution was dialysed until its conductivity was measured to be less than 100 ⁇ Scm '1 .
  • the solution was then evaporated to dryness or filtered through Whatman GF/C and 0.45 ⁇ m filter papers to obtain a purified ammonium salt suitable for use directly in an ink as described below.
  • Inks separately comprising each exemplified dye were prepared by dissolving 2 parts of the ammonium salt, prepared as described above, in 98 parts of a mixture of water and 2-pyrrolidone (in a respective ratio of 90:10 by volume).
  • inks were printed onto plain paper using a thermal ink-jet printer to give a bright yellow print which had good optical density and light fastness.
  • Further inks comprising the exemplified dyes may be may be prepared as described in the following tables in which the number in the first column (headed Ex no ) denotes the example number of dye to be used in the ink
  • the dye may be in its free acid form and/or in the form of any suitable salt (e g ammonium salt)
  • Numbers quoted in the second column onwards refer to the number of parts of the relevant ingredient and all parts are by weight
  • the inks may be applied to paper by thermal or piezo ink jet printing
  • MEOH methanol
  • 2P 2-pyroll ⁇ done
  • MIBK methylisobutyl ketone
  • CET cetyl ammonium bromide
  • TBT tertiary butanol
  • TDG thiodiglycol
  • BDL butane-2,3-d ⁇ ol
  • PHO Na 2 HP0 4
  • P12 propane-1 ,2-d ⁇ ol

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)

Abstract

Des colorants azoïques représentés par la formule générale (1) conviennent particulièrement comme colorants pour une imprimante à jet d'encre. Cette formule comporte toute forme appropriée du composé, notamment sous forme de sel, sous forme stéréoisomère, zwittérion, polymorphe, complexe, isotopique, des combinaisons de ces formes dans les mêmes espèces et des mélanges de ces formes. Dans cette formule, n représente une valeur comprise entre 1 et 5, R?1, R1B, R4 et R4B¿ comprennent chacun, indépendamment les uns des autres, au moins un des substituants suivants éventuellement substitué: H¿1?, C1-8alkyle; C1-8alcoxy; -NHCOH, C1-8alkylcarbonylamino, et -NHCONRR?5R6 où R5 et R6¿ comprennent chacun, indépendamment l'un de l'autre, au moins un des substituants suivants: H, C¿1-8?alkyle et aryle ; et R?2, R3¿ comprennent chacun, indépendamment les uns des autres, au moins un des substituants suivants éventuellement substitué: H; C¿1-8?alcoxy; -NHC1-8alkylèneOH, -SC1-8alkylèneSO3H; -NHC1-8alkylèneN(C1-8alkyle)2; (a) où X comprend l'un des substituants suivants: -NHC1-8alkylène; -NHphénylSO2NHC1-8alkylène; et une liaison directe, (b) où X comprend l'un des substituants suivants: -NHC1-8alkylène; -NHphénylSO2NHC1-8alkylène; et une liaison directe, une fraction du composé de la formule (2) où m et p valent chacun indépendamment l'un de l'autre de 0 à 5 inclus sous réserve que (m + p) soient compris entre 1 et 5 inclus, et R?1A, R2A, R4A et R4C¿ comprennent chacun, indépendamment les uns des autres, au moins un des substituants éventuellement substitué défini ci-dessus pour R?1, R2, R4 et R4B¿ respectivement; et tout autre substituant approprié labile ou non labile non mentionné ci-dessus; où les substituants éventuels précités comprennent: C¿1-4? (éventuellement substitué par au moins un radical halo), C1-4alcoxy (éventuellement substitué par au moins un radical halo), des radicaux carboxy, sulfo, hydroxy, amino, mercapto, cyano, nitro et halo.
PCT/GB1997/002377 1996-09-19 1997-09-05 Colorant azoique pour imprimante a jet d'encre WO1998012263A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
GB9902959A GB2332441B (en) 1996-09-19 1997-09-05 Azo dyes for ink-jet printing
AU41260/97A AU4126097A (en) 1996-09-19 1997-09-05 Azo dyer for ink-jet printing
US09/269,061 US6290763B1 (en) 1996-09-19 1997-09-05 AZO dyes and compositions comprising such dyes

Applications Claiming Priority (32)

Application Number Priority Date Filing Date Title
GB9619574.8 1996-09-19
GB9619589.6 1996-09-19
GB9619585.4 1996-09-19
GBGB9619572.2A GB9619572D0 (en) 1996-09-19 1996-09-19 Bisazo inkjet dyes
GB9619593.8 1996-09-19
GB9619612.6 1996-09-19
GB9619570.6 1996-09-19
GB9619572.2 1996-09-19
GBGB9619592.0A GB9619592D0 (en) 1996-09-19 1996-09-19 Bisazo inkjet dyes
GBGB9619593.8A GB9619593D0 (en) 1996-09-19 1996-09-19 Bisazo inkjet dyes
GB9619592.0 1996-09-19
GBGB9619571.4A GB9619571D0 (en) 1996-09-19 1996-09-19 Monoazo inkjet dyes
GBGB9619574.8A GB9619574D0 (en) 1996-09-19 1996-09-19 Monoazo inkjet dyes
GB9619584.7 1996-09-19
GB9619587.0 1996-09-19
GBGB9619612.6A GB9619612D0 (en) 1996-09-19 1996-09-19 Bizao inkjet dyes
GB9619571.4 1996-09-19
GBGB9619589.6A GB9619589D0 (en) 1996-09-19 1996-09-19 Monoazo inkjet dyes
GBGB9619586.2A GB9619586D0 (en) 1996-09-19 1996-09-19 Monoazo inkjet dyes
GBGB9619587.0A GB9619587D0 (en) 1996-09-19 1996-09-19 Monoazo inkjet dyes
GBGB9619590.4A GB9619590D0 (en) 1996-09-19 1996-09-19 Bisazo inkjet dyes
GBGB9619584.7A GB9619584D0 (en) 1996-09-19 1996-09-19 Bisazo inkjet dyes
GB9619575.5 1996-09-19
GBGB9619585.4A GB9619585D0 (en) 1996-09-19 1996-09-19 Bisazo inkjet dyes
GBGB9619570.6A GB9619570D0 (en) 1996-09-19 1996-09-19 Monoazo inkjet dyes
GB9619591.2 1996-09-19
GBGB9619575.5A GB9619575D0 (en) 1996-09-19 1996-09-19 Bisazo inkjet dyes
GBGB9619588.8A GB9619588D0 (en) 1996-09-19 1996-09-19 Monoazo inkjet dyes
GB9619590.4 1996-09-19
GB9619588.8 1996-09-19
GB9619586.2 1996-09-19
GBGB9619591.2A GB9619591D0 (en) 1996-09-19 1996-09-19 Monoazo inkjet dyes

Publications (1)

Publication Number Publication Date
WO1998012263A1 true WO1998012263A1 (fr) 1998-03-26

Family

ID=27585625

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB1997/002377 WO1998012263A1 (fr) 1996-09-19 1997-09-05 Colorant azoique pour imprimante a jet d'encre

Country Status (3)

Country Link
AU (1) AU4126097A (fr)
GB (1) GB2332441B (fr)
WO (1) WO1998012263A1 (fr)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0918074A1 (fr) * 1997-11-20 1999-05-26 ILFORD Imaging Switzerland GmbH Colorants azoiques, leur préparation et utilisation
EP1031614A1 (fr) * 1999-02-23 2000-08-30 ILFORD Imaging Switzerland GmbH Colorants chromorésistants, leur préparation et leur utilisation
WO2003008509A1 (fr) * 2001-07-19 2003-01-30 Cabot Corporation Compositions d'encre contenant des pigments colores modifies et procedes de fabrication de ces compositions
JP2006152264A (ja) * 2004-10-26 2006-06-15 Nippon Kayaku Co Ltd 水溶性アゾ化合物、インク組成物および着色体
WO2007049366A1 (fr) * 2005-10-25 2007-05-03 Nippon Kayaku Kabushiki Kaisha Compose azoique hydrosoluble, composition d’encre et materiau colore
US7771525B2 (en) 2006-11-01 2010-08-10 Nippon Kayaku Kabushiki Kaisha Water-soluble azo compound or salt thereof, ink composition and colored product

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0468647A1 (fr) * 1990-07-26 1992-01-29 Zeneca Limited Composés anioniques
EP0612820A2 (fr) * 1993-02-26 1994-08-31 Canon Kabushiki Kaisha Encre procédé d'enrégistrement à jet d'encre et appareil
EP0669381A2 (fr) * 1994-02-28 1995-08-30 Canon Kabushiki Kaisha Colorant, encre contenant ce colorant, et méthode d'enregistrement par jet d'encre et instrument utilisant cette encre
EP0719847A1 (fr) * 1994-04-25 1996-07-03 Seiko Epson Corporation Composition d'encre a base d'eau et procede d'impression avec cette encre

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0468647A1 (fr) * 1990-07-26 1992-01-29 Zeneca Limited Composés anioniques
EP0612820A2 (fr) * 1993-02-26 1994-08-31 Canon Kabushiki Kaisha Encre procédé d'enrégistrement à jet d'encre et appareil
EP0669381A2 (fr) * 1994-02-28 1995-08-30 Canon Kabushiki Kaisha Colorant, encre contenant ce colorant, et méthode d'enregistrement par jet d'encre et instrument utilisant cette encre
EP0719847A1 (fr) * 1994-04-25 1996-07-03 Seiko Epson Corporation Composition d'encre a base d'eau et procede d'impression avec cette encre

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0918074A1 (fr) * 1997-11-20 1999-05-26 ILFORD Imaging Switzerland GmbH Colorants azoiques, leur préparation et utilisation
US6068687A (en) * 1997-11-20 2000-05-30 Ilford Imaging Switzerland Gmbh Azo dyes and their preparation and use
EP1031614A1 (fr) * 1999-02-23 2000-08-30 ILFORD Imaging Switzerland GmbH Colorants chromorésistants, leur préparation et leur utilisation
US6320031B1 (en) 1999-02-23 2001-11-20 Ilford Imaging Switzerland Gmbh Monoazo dyes and their preparation and use
WO2003008509A1 (fr) * 2001-07-19 2003-01-30 Cabot Corporation Compositions d'encre contenant des pigments colores modifies et procedes de fabrication de ces compositions
US6641653B2 (en) 2001-07-19 2003-11-04 Cabot Corporation Ink compositions comprising modified colored pigments and methods for preparing the same
JP2006152264A (ja) * 2004-10-26 2006-06-15 Nippon Kayaku Co Ltd 水溶性アゾ化合物、インク組成物および着色体
WO2007049366A1 (fr) * 2005-10-25 2007-05-03 Nippon Kayaku Kabushiki Kaisha Compose azoique hydrosoluble, composition d’encre et materiau colore
US7740696B2 (en) 2005-10-25 2010-06-22 Nippon Kayaku Kabushiki Kaisha Water-soluble azo compound, ink composition, and colored article
US7771525B2 (en) 2006-11-01 2010-08-10 Nippon Kayaku Kabushiki Kaisha Water-soluble azo compound or salt thereof, ink composition and colored product

Also Published As

Publication number Publication date
GB9902959D0 (en) 1999-03-31
GB2332441A (en) 1999-06-23
GB2332441B (en) 2001-03-21
AU4126097A (en) 1998-04-14

Similar Documents

Publication Publication Date Title
EP0979253B1 (fr) Colorants a base de phtalocyanine pour encres d'imprimantes a jet d'encre
US6488752B1 (en) Monoazo dyestuffs, a composition and an ink for ink jet printing comprising them
EP1239010B1 (fr) Phthalocyanines, compositions et leur utilisation
US6569212B2 (en) Phthalocyanine ink-jet dyes
EP1093492B1 (fr) Composes de phtalocyanine et leurs utilisations
US6277185B1 (en) Dye compounds, compositions containing them and their use
US6290763B1 (en) AZO dyes and compositions comprising such dyes
EP1009775B1 (fr) Composes de phtalocyanine utilises dans les encres pour impression a jet d'encre
EP0975698B1 (fr) Colorants a base de phtalocyanine pour encres d'imprimantes a jet d'encre
US5891230A (en) Bisazo ink-jet dyes
US6332918B1 (en) Phthalocyanine compounds for ink-jet printing
WO1998012263A1 (fr) Colorant azoique pour imprimante a jet d'encre
US6712893B1 (en) Dis-azo dyestuffs and use thereof in ink-jet printing
JPH09208843A (ja) 化合物
US6517620B1 (en) Mono-azo dyes and inks for ink-jet printing
US6344076B1 (en) Monoazo dyes and inks containing them
US6746525B1 (en) Disazo dyes and inks containing them
US6514329B1 (en) Mono-azo dyes and inks for ink-jet printing
GB2341868A (en) Sulpho and phenylaminosulphonyl substituted phthalocyanine derivatives and their use in ink jet inks
EP1871840A2 (fr) Colorants disazoiques pour impression a jet d'encre
US6736888B1 (en) Disazo dyes and inks containing them
US6695899B1 (en) Disazo dyestuffs for ink jet printing
US20090142553A1 (en) Yellow Dye and a Process for Ink Jet Printing Using the Dye
JPH09208844A (ja) 化学化合物
US20080233289A1 (en) Dyes Comprising [(4-[2-Amino-3,6-Disulpho-8-Hydroxynaphth-1-Ylazo]Anilino)- 1,3,5-Triazinyl] Moities

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AL AM AT AU AZ BA BB BG BR BY CA CH CN CU CZ DE DK EE ES FI GB GE GH HU IL IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MD GH

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): GH KE LS MW SD SZ UG ZW AT BE CH DE DK ES FI FR GB GR IE IT LU MC NL PT SE

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
121 Ep: the epo has been informed by wipo that ep was designated in this application
WWE Wipo information: entry into national phase

Ref document number: 09269061

Country of ref document: US

NENP Non-entry into the national phase

Ref country code: JP

Ref document number: 1998514376

Format of ref document f/p: F

REG Reference to national code

Ref country code: DE

Ref legal event code: 8642

122 Ep: pct application non-entry in european phase
NENP Non-entry into the national phase

Ref country code: CA