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
  • C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
  • C09B31/16—Trisazo dyes
  • C09B31/26—Trisazo dyes from other coupling components "D"
  • C09B31/28—Heterocyclic compounds
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
  • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
  • Y10T428/00—Stock material or miscellaneous articles
  • Y10T428/24—Structurally defined web or sheet [e.g., overall dimension, etc.]
  • Y10T428/24802—Discontinuous or differential coating, impregnation or bond [e.g., artwork, printing, retouched photograph, etc.]

Definitions

• B is optionally substituted phenylene or naphthylene; n is 0 or 1 ; and D is a pyrazolonyl group; wherein the liquid medium comprises an organic solvent.
• the optional substituents on B are preferably selected from carboxy, sulpho, phosphato, optionally substituted amino, acylamino, optionally substituted ureido, optionally substituted alkyl, optionally substituted alkoxy and optionally substituted aryl.
• B When B is substituted phenylene it preferably carries one or more groups selected from optionally substituted C ⁇ -alkyl, optionally substituted C 1-e -alkyIthio, optionally substituted C 1-6 -alkoxy, optionally substituted amino, optionally substituted ureido, carboxy and sulphate
• the naphthylene ring When B is optionally substituted naphthylene the naphthylene ring preferably carries one or more water solubilising groups, more preferably by one or two groups selected from carboxyl, sulphonic and phosphonic acid groups.
• optionally substituted phenylene and naphthylene groups represented by B there may be mentioned 7-sulphonaphth-1 ,4-ylene, naphth-1 ,4-ylene, 2,5-dimethoxyphen-1 ,4-ylene, 2,5-di(2-hydroxyethoxy)phen-1 ,4-ylene and 2-methoxy-5- methylphen-1 ,4-ylene.
• D is a pyrazolonyl group carrying at least one carboxy, sulpho or phosphato group.
• D is preferably a pyrazolonyl group of Formula (2a) or Formula (
• Preferred optionally substituted C ⁇ -alkoxy groups are optionally substituted C M -alkyl, more preferably C ⁇ -alkyl which is unsubstituted or carries a carboxy, sulpho or phosphato group.
• Preferred optionally substituted phenyl groups are those mentioned above for A.
• Preferred optionally substituted sulphonamide groups are of the formula
• optionally substituted amino groups are optionally substituted acylamino, especially C ⁇ -acylamino, more preferably optionally substituted ureido which is unsubstituted or carries a carboxy, sulpho or phosphato group.
• acyl groups are optionally substituted C ⁇ alkylacyl, optionally substituted phenylacyl, preferably acetyl or benzoyl.
• R 1 there may be mentioned methyl, carboxy and H.
• R 2 and R 3 are preferably each independently an optionally substituted aryl group, more preferably phenyl or phenyl carrying one or two substituents selected from carboxy and sulpho.
• D is of Formula (2a) or (2b); R 1 is H, methyl or carboxy; and
• Reaction conditions are those generally used in the dyestuff art, for example as described in for example EP 0356080.
• the preferred salts are alkali metal salts (especially lithium, sodium and potassium salts), ammonium and substituted ammonium salts and mixtures thereof.
• alkali metal salts especially lithium, sodium and potassium salts
• ammonium and substituted ammonium salts and mixtures thereof are especially preferred salts.
• Especially preferred salts are sodium, potassium and lithium salts, salts with ammonia and volatile amines and mixtures thereof.
• the lithium salts have good solubility, forming particularly storage stable inks with low toxicity and no tendency to block ink jet nozzles.
• the compounds may be converted into a desired salt using known techniques.
• the dyes are completely in the form of the ammonium salt or substituted ammonium salt and mixed alkali metal and either ammonium salt or substituted ammonium salt are effective, especially those in which at least 50% of the cations are ammonium or substituted ammonium ions.
• Still further salts are those with the counter ions described in US 5,830,265, claim 1 , integer (b), which are included herein by reference thereto.
• the compounds of Formula (1) may exist in tautomeric forms other than those shown in this specification. These tautomers are included within the scope of the present claims.
• a preferred composition comprises: (a) from 0.01 to 30 parts of a compound of Formula (1 ) or salt thereof; and
• 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 20°C of at least 10%. This allows the preparation of liquid dye concentrates which may be used to prepare inks and reduces the chance of the dye precipitating if evaporation of the liquid medium occurs during storage.
• Preferred water-miscible organic solvents include C ⁇ -alkanols, preferably methanol, ethanol, n-propanol, isopropanol, n-butanol, sec-butanol, tert-butanol, n-pentanol, cyclopentanol and cyclohexanol; linear amides, preferably dimethylformamide or dimethylacetamide; ketones and ketone-alcohols, preferably acetone, methyl ether ketone, cyclohexanone and diacetone alcohol; water-miscible ethers, preferably tetrahydrofuran and dioxane; diols, preferably diols having from 2 to 12 carbon atoms, for example pentane-1 ,5-diol, ethylene glycol, propylene glycol, butylene glycol, pentylene glycol, hexylene glycol and thiodiglycol
• Especially preferred water-soluble organic solvents are cyclic amides, especially 2- pyrrolidone, N-methyl-pyrrolidone and N-ethyl-pyrrolidone; diols, especially 1 ,5-pentane diol, ethyleneglycol, thiodiglycol, diethyleneglycol and triethyleneglycol; and mono- C ⁇ -alkyl and C ⁇ -alkyl ethers of diols, more preferably mono- C ⁇ -alkyl ethers of diols having 2 to 12 carbon atoms, especially ((2-methoxy-2)-ethoxy)-2-ethoxyethanol.
• the dyes of the invention may be used as the sole colorant in inks because of their attractive black shade. However, if desired, one may combine the present compounds with one or more further colorants if a slightly different shade is required for a particular end use.
• the further colorants are preferably dyes. When further colorants are included in the ink these are preferably selected from black, magenta and yellow colorants and combinations thereof. Suitable further black colorants include C.I. Food Black 2, C.I. Direct Black 19,
• C.I.Reactive Black 31 PRO-JETTM Fast Black 2, C.I. Direct Black 195; C.I.Direct Black 168; and black dyes described in patents by Lexmark (e.g. EP 0 539,178 A2, Example 1 , 2, 3, 4 and 5), Orient Chemicals (e.g. EP 0 347 803 A2, pages 5-6, azo dyes 3, 4, 5, 6, 7, 8, 12, 13, 14, 15 and 16) and Seiko Epson Corporation.
• Suitable further magenta colorants include PRO-JETTM Fast Magenta 2.
• Suitable further yellow colorants include C.I.Direct Yellow 142; C.I.Direct Yellow 132; C.I.Direct Yellow 86; C.I.Direct Yellow 85; C.I. Direct Yellow 173; and C.I.Acid Yellow 23.
• the ink may also contain additional components conventionally used in ink jet printing inks, for example viscosity and surface tension modifiers, corrosion inhibitors, biocides, kogation reducing additives and surfactants which may be ionic or non-ionic.
• the pH of the composition is preferably from 4 to 11 , more preferably from 7 to 10.
• the viscosity of the composition at 25°C is preferably less than 50cP, more preferably less than 20 cP and especially less than 5cP.
• a further aspect of the invention provides a process for printing an image on a substrate comprising applying thereto a composition according to the first aspect of the present invention to the substrate by means of an ink jet printer.
• the substrate is preferably paper, plastic, a textile, metal or glass, more preferably a treated substrate such as a coated paper or coated plastic, especially coated paper.
• Preferred plain or treated papers are papers which may have an acid, alkaline or neutral character. Examples of commercially available treated papers include HP Premium Coated Paper, HP Photopaper (both available from Hewlett Packard Inc.); Stylus Pro 720 dpi Coated Paper, Epson Photo Quality Glossy Film, Epson Photo Quality Glossy Paper (all available from Seiko Epson Corp.); Canon HR 101 High Resolution Paper, Canon GP 201 Glossy Paper, Canon HG 101 and HG201 High Gloss Film and Canon PR101 (all available from Canon).
• a further aspect of the present invention provides a paper, an overhead projector slide or a textile material printed with a composition , a compound or by means of a process as hereinbefore defined.
• a still further aspect of the present invention provides an ink jet printer cartridge, optionally refillable, comprising one or more chambers and a composition, wherein the composition is present in at least one of the chambers and the composition is according to the second aspect of the present invention.
• the present compounds and compositions provide prints of attractive, neutral black shades which are particularly well suited for the ink jet printing of text and images.
• the compositions have good storage stability and low tendency to block the very fine nozzles used in ink jet printers.
• the resultant images have good optical density, light- fastness, wet-fastness and resistance to fading in the presence of oxidising air pollutants. This is achieved without the need for copper or other transition metals used in the dyes of US 2001/0027734.
• the dyes of the present invention are simpler to make and more environmentally friendly than the metallised dyes of US 2001/0027734.
• 2-Sulpho-4-methoxyaniline (20.3g, 0.1M) was stirred in water (150ml) at room temperature and 2N NaOH added to form a solution at pH 8.0.
• 2N NaNO 2 solution 50ml was added and the mixture stirred to homogenise.
• the solution was added gradually to a mixture of ice/water (150ml) and 36% HCI (40ml) at 5°C and the resulting suspension stirred for 2 hours at 0-10 °C.
• Sulphamic acid solution (10%) was added in order to remove excess nitrous acid.
• 2,5-Dimethoxyaniline (28.5g, 0.1M) was dissolved in water (300ml) and cooled to room temperature. The resulting suspension was added to the above diazo suspension at 0-10 °C and the pH adjusted to 4.5 by the addition of sodium acetate. The mixture was stirred for 18 hours and the dye collected by filtration and washed with water (100ml).
• the resultant diazonium salt suspension was then slowly added to a solution of 1-(4-sulphophenyl)-5- pyrazolone-3-carboxylic acid (4.51 g, obtained from Pfaltz & Bauer) in water (200ml) at pH 7 (lithium hydroxide) at 0-10°C, maintaining the pH at 6-7 by addition of lithium hydroxide (2 M). After stirring for a further 1 hour the temperature was raised to 30°C and lithium chloride 25% w/v was added (exothermic). The stirred suspension was allowed to self- cool to 50°C and the product was then isolated by filtration.
• Example 1 The method of Example 1 was repeated except that 2,5-dimethoxyaniline in Stage A was replaced by 2-methyl-5-methoxyaniline.
• Example 3 The method of Example 3 was repeated except that Gamma acid in Stage B was replaced by 1-hydroxy-8-amino-3,6-naphthylene disulphonic acid.
• SurfynolTM 465 is a surfactant available from Air Products and Chemicals Inc., USA.
• inks were prepared according to Tables 1 and 2 wherein the dye described in the first column is the dye made in the above example of the same number. 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.
• IPA isopropanol
• MEOH methanol
• MIBK methylisobutyl ketone
• P12 propane-1 ,2-diol
• BDL butane-2,3-diol
• TBT tertiary butanol
• TDG thiodiglycol
• Example 4 The inks prepared in Example 4 were printed onto the substrates indicated in Table 5 using a HP560TM ink jet printer. The printed substrates were then assessed for ozone fastness using an ozone test cabinet from Hampden Test Equipment. The exposures to ozone were carried out for 24 hours at 40°C and 50% relative humidity in the presence of 1 part per million of ozone. Ozone-fastness was judged by measuring the optical density before and after exposure to ozone using a Gretag Spectrolino SpectrodensitometerTM. Thus, the lower the %OD loss the greater the ozone fastness. The results are shown in Table 5 where the example number of the dye used to prepare the ink is indicated in the left hand column. These clearly demonstrate that inks based on compositions of this invention display good ozone fastness. Table 5

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)
• Ink Jet Recording Methods And Recording Media Thereof (AREA)
• Ink Jet (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Coloring (AREA)

Priority Applications (6)

Applications Claiming Priority (2)

Publications (1)

Family

ID=9936496

Family Applications (2)

Family Applications After (1)

Country Status (8)

Cited By (7)

Families Citing this family (15)

Citations (3)

Family Cites Families (28)

• 2002
  • 2002-05-11 GB GBGB0210824.9A patent/GB0210824D0/en not_active Ceased
• 2003
  • 2003-05-08 EP EP03722842A patent/EP1506260B1/en not_active Expired - Lifetime
  • 2003-05-08 DE DE60330139T patent/DE60330139D1/de not_active Expired - Fee Related
  • 2003-05-08 AT AT03725383T patent/ATE449137T1/de not_active IP Right Cessation
  • 2003-05-08 US US10/513,750 patent/US7052538B2/en not_active Expired - Fee Related
  • 2003-05-08 WO PCT/GB2003/002007 patent/WO2003095563A1/en not_active Ceased
  • 2003-05-08 AT AT03722842T patent/ATE444995T1/de not_active IP Right Cessation
  • 2003-05-08 JP JP2004503561A patent/JP2005529990A/ja active Pending
  • 2003-05-08 AU AU2003230002A patent/AU2003230002A1/en not_active Abandoned
  • 2003-05-08 JP JP2004503562A patent/JP2005525449A/ja not_active Withdrawn
  • 2003-05-08 DE DE60329590T patent/DE60329590D1/de not_active Expired - Fee Related
  • 2003-05-08 AU AU2003227918A patent/AU2003227918A1/en not_active Abandoned
  • 2003-05-08 US US10/513,472 patent/US7041161B2/en not_active Expired - Fee Related
  • 2003-05-08 EP EP03725383A patent/EP1506261B1/en not_active Expired - Lifetime
  • 2003-05-08 WO PCT/GB2003/001981 patent/WO2003095562A1/en not_active Ceased

Patent Citations (3)

Non-Patent Citations (2)

Also Published As

Similar Documents

Legal Events