GB2464188A - Dyes and inks suitable for use in ink jet printing - Google Patents

Dyes and inks suitable for use in ink jet printing Download PDF

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Publication number
GB2464188A
GB2464188A GB0917208A GB0917208A GB2464188A GB 2464188 A GB2464188 A GB 2464188A GB 0917208 A GB0917208 A GB 0917208A GB 0917208 A GB0917208 A GB 0917208A GB 2464188 A GB2464188 A GB 2464188A
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Prior art keywords
optionally substituted
formula
ink
compound
group
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GB0917208D0 (en
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Gavin Wright
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Fujifilm Imaging Colorants Ltd
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Fujifilm Imaging Colorants Ltd
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Priority claimed from GB0818703A external-priority patent/GB0818703D0/en
Priority claimed from GB0818708A external-priority patent/GB0818708D0/en
Priority claimed from GB0818706A external-priority patent/GB0818706D0/en
Priority claimed from GB0818709A external-priority patent/GB0818709D0/en
Priority claimed from GB0818710A external-priority patent/GB0818710D0/en
Priority claimed from GB0818707A external-priority patent/GB0818707D0/en
Priority claimed from GB0818704A external-priority patent/GB0818704D0/en
Priority claimed from GB0818705A external-priority patent/GB0818705D0/en
Application filed by Fujifilm Imaging Colorants Ltd filed Critical Fujifilm Imaging Colorants Ltd
Publication of GB0917208D0 publication Critical patent/GB0917208D0/en
Publication of GB2464188A publication Critical patent/GB2464188A/en
Withdrawn legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
    • C07D221/18—Ring systems of four or more rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
    • C07D275/04—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
    • C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
    • C09B5/02—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic ring being only condensed in peri position
    • 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
    • C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
    • C09B5/02—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic ring being only condensed in peri position
    • C09B5/022—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic ring being only condensed in peri position not provided for in one of the sub groups C09B5/04 - C09B5/20
    • C09B5/026—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic ring being only condensed in peri position not provided for in one of the sub groups C09B5/04 - C09B5/20 only S-containing hetero rings
    • 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
    • C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
    • C09B5/02—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic ring being only condensed in peri position
    • C09B5/10—Isothiazolanthrones; Isoxazolanthrones; Isoselenazolanthrones
    • 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
    • C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
    • C09B5/02—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic ring being only condensed in peri position
    • C09B5/14—Benz-azabenzanthrones (anthrapyridones)
    • 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
    • C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
    • C09B5/02—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic ring being only condensed in peri position
    • C09B5/16—Benz-diazabenzanthrones, e.g. anthrapyrimidones
    • 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

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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)
  • Inks, Pencil-Leads, Or Crayons (AREA)

Abstract

Anthraquinone type dyes of formulae (1) - (8) (wherein all variables are defined in claim 1) may be useful as magenta dyes for use in ink jet printing.

Description

MAGENTA DYES AND INKS FOR USE IN INK-JET PRINTING
This invention relates to dyes, compositions and inks for ink-jet printers, to printing processes, to printed substrates and to ink-jet printer cartridges.
Ink-jet printing 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 set of inks used in this technique typically comprise yellow, magenta, cyan and black inks.
With the advent of high-resolution digital cameras and ink-jet printers it is becoming increasingly common for consumers to print off photographs using an ink-jet printer.
While ink-jet printers have many advantages over other forms of printing and image development there are still technical challenges to be addressed. For example, there are the contradictory requirements of providing ink colorants that are soluble in the ink medium and yet display excellent wet-fastness (i.e. prints do not run or smudge when printed). The inks also need to dry quickly to avoid sheets sticking together after they have been printed, but they should not form a crust over the tiny nozzles in the printer head. Storage stability is also important to avoid particle formation that could block the tiny nozzles used in the printer especially since consumers can keep an ink-jet ink cartridge for several months.
Furthermore, and especially important with photographic quality reproductions, the resultant images should not fade rapidly on exposure to light or common oxidising gases such as ozone. It is also important that the shade and chroma of the colorant are exactly right so that an image may be optimally reproduced.
Thus developing new inks and colorants for ink-jet printing presents a unique challenge in balancing all these conflicting and demanding properties.
The present invention provides compounds of Formulae (1) to (8) and salts thereof: (R1) R2 Forrnula(1) wherein: R2 is an optionally substituted hydrocarbyl group; R4 is optionally substituted aryl, optionally substituted heterocyclyl or n is 0 to 4; wherein the compound of Formula (1) carries at least one substituent selected from the group consisting of-SO3H, -CO2H, -COSH or -P03H2; R3)N-R (R1) (IIIIIXIIJ o NH R5 Formula (2) wherein: R6 is optionally substituted aryl or optionally substituted heteroaryl; n is 0 to 4; and wherein the compound of Formula (2) carries at least one substituent selected from the group consisting of-SO3H, -CO2H, -COSH or -P03H2;
-z X (R1) o A
Formula (3) wherein: R2 is an optionally substituted hydrocarbyl group; A is S, 0 or NR7; R7 is H, optionally substituted alkyl, optionally substituted aryl or optionally nisoto4; one of X, Y and Z is -S-; one of X, Y and Z is -C(=0)-; and one of X, Y and Z is optionally substituted carbon: and wherein the compound of Formula (3) carries at least one substituent selected from the group consisting of -SO3H, -CO2H, -COSH or -P03H2; x2
NN
(R1) IIIIiIIIIJiE o S Formula (4) wherein: R2 is an optionally substituted hydrocarbyl group; X2 is H, optionally substituted alkyl, optionally substituted aryl or optionally n is 0 to 4; and provided that the compound of Formula (4) carries at least one substituent selected from the group consisting of -SO3H, -CO2H, -.COSH and -P03H2; x2
NN (R1) o R2
Formula (5) wherein: R2 is an optionally substituted hydrocarbyl group; X2 is H, optionally substituted alkyl, optionally substituted aryl or optionally n is 0 to 4; and provided that (i) the compound of Formula (5) carries at least one substituent selected from the group consisting of-SO3H, -CO2H, -COSH and -P03H2; and (ii) X2 and R2 are not both phenyl; (R8) 0 A Formula (6) wherein: R8 is -SO3H, -CO2H, -COSH or -P03H2, halo, nitro, cyano, CORd, CONRdRe, SO2NRdRe or SO2Rd where Rd and Re are each independently H, optionally substituted alkyl or optionally substituted aryl; R2 is an optionally substituted hydrocarbyl group; A is S, 0 or NR7; R7 is H, optionally substituted alkyl, optionally substituted aryl or optionally n is 0 to 4; X3 and Y2 together with the anthrone ring to which they are attached form a 5-membered optionally substituted fused heterocyclic ring system wherein one of X3 and Y2 is N and the other is 0, S or optionally substituted carbon: wherein the compound of Formula (6) carries at least one substituent selected from the group consisting of is -SO3H, -CO2H, -COSH or -P03H2; and provided that the compound of Formula (6) is not of Formula (a) or a salt thereof
ONQ
Formula (a); x4 (R1) 0 A Formula (7) wherein: R2 is an optionally substituted hydrocarbyl group; A is S or 0; n is 0 to 4; one of X4, Y3 and Z2 is -NR3-; one of X4, Y3 and Z2 is -C(=O)-; and one of X4, Y3 and Z2 is optionally substituted carbon; and
ZX
(R1) I I 0 NR
R
Formula (8) wherein: R2 is an optionally substituted hydrocarbyl group; R7 is H, optionally substituted alkyl, optionally substituted aryl or optionally nisoto4; one of X5, Y4 and Z3 is -NR4-; one of X5, Y4 and Z3 is -C(=O)-; and one of X5, Y4 and Z3 is carbon carrying an optionally substituted aryl or ON; and R1 and R3, when it is a substituent, are preferably independently selected from: optionally substituted alkyl (preferably 014-alkyl), optionally substituted alkenyl (preferably C14-alkenyl), optionally substituted alkynyl (preferably 014-alkynyl), optionally substituted alkoxy (preferably 014-alkoxy), optionally substituted aryl (preferably phenyl), optionally substituted aryloxy (preferably phenoxy), optionally substituted heterocyclyl (including heteroaryl), polyalkylene oxide (preferably polyethylene oxide or polypropylene oxide), 002H, SO3H, P03H2, nitro, cyano, halo, ureido, -SO2F, hydroxy, ester, sulfate, NRaRb, OONRaRb, NHOORa, carboxyester, sulfone, and SO2NRaRb wherein Ra and Rb are each independently H, optionally substituted alkyl (especially 014-alkyl), SRc, - ORc, -NH-Rc, wherein Rc is optionally substituted alkyl (preferably 014-alkyl), optionally substituted alkenyl (preferably 014-al kenyl), optionally substituted alkynyl (preferably C14-alkynyl), optionally substituted alkoxy (preferably 014-alkoxy), optionally substituted aryl (preferably phenyl), optionally substituted aryloxy (preferably phenoxy), optionally substituted heterocyclyl, polyalkylene oxide (preferably polyethylene oxide or polypropylene oxide), optional substituents for any of the above substituents may be selected from the same list of substituents.
Preferably R1 and R3, when it is a substituent, are independently -SO3H, -CO2H, -COSH or -P03H2, halo, nitro, cyano, CORd or _CONRdRe or SO2NRdRe, SORd, where Rd and Re are each independently H, optionally substituted alkyl (especially optionally substituted C14-alkyl) or optionally substituted aryl (especially optionally substituted phenyl).
R2 is preferably optionally substituted aryl, especially optionally substituted phenyl or optionally substituted naphthyl; optionally substituted alkyl, especially optionally substituted C14-alkyl or optionally substituted heterocyclyl, wherein the optional substituents may be selected from the list given above for R' and R3.
More preferably R2 is phenyl bearing one or two substituents selected from the group consisting of -SO3H and -CO2H; heteroaryl bearing one or two substituents selected from the group consisting of -SO3H and -CO2H; optionally substituted C14-alkylsulfonamide; or optionally substituted C14-alkylcarbonamide.
Preferably R4 is optionally substituted phenyl or optionally substituted alky, wherein optional substituents may be selected from the list given above for R' and R3.
More preferably R4 is optionally substituted phenyl carrying, either directly or on a substituent, a group selected from -SO3H, -CO2H, -COSH and -P03H2; or optionally substituted C14 alkyl, especially methyl.
Preferably n is 0 or 1.
The compounds of Formulae (1) to (8) are preferably free from fibre reactive groups. The term fibre reactive group is well known in the art and is described for example in EP 0356014 Al. Fibre reactive groups are capable, under suitable conditions, of reacting with the hydroxyl groups present in cellulosic fibres or with the amino groups present in natural fibres to form a covalent linkage between the fibre and the dye. As examples of fibre reactive groups excluded from the compounds of Formulae (1) to (8) there may be mentioned aliphatic sulfonyl groups which contain a sulfate ester group in beta- position to the sulfur atom, e.g. beta-sulfato-ethylsulfonyl groups, alpha, beta-unsaturated acyl radicals of aliphatic carboxylic acids, for example acrylic acid, alpha-chloro-acrylic acid, alpha-bromoacrylic acid, propiolic acid, rnaleic acid and mono-and dichloro maleic; also the acyl radicals of acids which contain a substituent which reacts with cellulose in the presence of an alkali, e.g. the radical of a halogenated aliphatic acid such as chloroacetic acid, beta-chloro and beta-bromopropionic acids and alpha, beta-dichloro-and dibromopropionic acids or radicals of vinylsulfonyl-or beta-chloroethylsulfonyl-or beta-sulfatoethyl-sulfonyl-endo-methylene cyclohexane carboxylic acids. Other examples of cellulose reactive groups are tetrafluorocyclobutyl carbonyl, trifluoro-cyclobutenyl carbonyl, tetrafluorocyclobutylethenyl carbonyl, trifluoro-cyclobutenylethenyl carbonyl; activated halogenated 1,3-dicyanobenzene radicals; and heterocyclic radicals which contain 1, 2 or 3 nitrogen atoms in the heterocyclic ring and at least one cellulose reactive substituent on a carbon atom of the ring, for example a triazinyl halide.
Acid and basic groups on the compounds of Formula (1), particularly acid groups, are preferably in the form of a salt. Thus, the Formulae shown herein include the compounds in free acid and in salt form.
Preferred salts are alkali metal salts, especially lithium, sodium and potassium, ammonium and substituted ammonium salts (including quaternary amines such as ((CH3)4N) and mixtures thereof. Especially preferred are salts with sodium, lithium, ammonia and volatile amines, more especially sodium salts.
The compounds of Formulae (1) to (8) may be converted into a salt using known techniques.
The compounds of Formulae (1) to (8) may exist in tautomeric forms other than those shown in this specification. These tautomers are included within the scope of the present invention. However, tautomers may not bear a substituent on a hydroxy/enol oxygen.
These compounds according to the present invention may be prepared using processes well known to the skilled man. These processes are as described in W0200201 2402, which is incorporated herein by reference The compounds of Formulae (1) to (8) preferably have attractive strong red, violet or magenta shades (especially magenta) and are valuable colorants for use in the preparation of ink-jet printing inks. They benefit from a good balance of solubility, storage stability, resistance to bronzing and fastness to water, ozone and light. In particular they display excellent wet fastness and ozone fastness.
According to a second aspect of the present invention there is provided a composition comprising a compound of Formulae (1) to (8) and/or a salt thereof, as described in the first aspect of the invention, and a liquid medium.
Preferred compositions according to the second aspect of the invention comprise: (a) from 0.01 to 30 parts of a compound of Formulae (1) to (8) and salts thereof according to the first aspect of the invention; and (b) from 70 to 99.99 parts of a liquid medium; wherein all parts are by weight.
Preferably the number of parts of (a)+(b) = 100.
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 80 to 99.9, more preferably from 85 to 99.5 and especially from 95 to 99 parts.
Preferably component (a) is completely dissolved in component (b).
Preferably component (a) has a solubility in component (b) at 2000 of at least 10%. This allows the preparation of liquid dye concentrates that may be used to prepare more dilute inks and reduces the chance of the dye precipitating if evaporation of the liquid medium occurs during storage.
The inks may be incorporated in an ink-jet printer as a high concentration ink, a low concentration ink or both a high concentration and a low concentration ink. In the latter case this can lead to improvements in the resolution and quality of printed images. Thus the present invention also provides a composition (preferably an ink) where component (a) is present in an amount of 2.5 to 7 parts, more preferably 2.5 to 5 parts (a high concentration ink) or component (a) is present in an amount of 0.5 to 2.4 parts, more preferably 0.5 to 1.5 parts (a low concentration ink).
Preferred liquid media include water, a mixture of water and organic solvent and organic solvent free from water. Preferably the liquid medium comprises a mixture of water and organic solvent or organic solvent free from water.
When the liquid medium (b) comprises a mixture of water and organic solvent, 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.
It is preferred that the organic solvent present in the mixture of water and organic solvent is a water-miscible organic solvent or a mixture of such solvents.
Preferred water-miscible organic solvents include 016-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 and oligo-and poly-alkyleneglycols, preferably diethylene glycol, triethylene glycol, polyethylene glycol and polypropylene glycol; triols, preferably glycerol and 1,2,6-hexanetriol; mono-014-alkyl ethers of diols, preferably mono-01 4-alkyl ethers of diols having 2 to 12 carbon atoms, especially 2-methoxyethanol, 2-(2-methoxyethoxy)ethanol, 2-(2-ethoxyethoxy)-ethanol, 2-[2-(2-methoxyethoxy)ethoxy]ethanol, 2-[2-(2-ethoxyethoxy)-ethoxy]-ethanol and ethyleneglycol monoallylether; cyclic amides, preferably 2-pyrrolidone, N-methyl- 2-pyrrolidone, N-ethyl-2-pyrrolidone, caprolactam and 1,3-dimethylimidazolidone; cyclic esters, preferably caprolactone; sulfoxides, preferably dimethyl sulfoxide; and sulfones, preferably sulfolane. Preferably the liquid medium comprises water and 2 or more, especially from 2 to 8, water-miscible organic solvents.
Especially preferred water-miscible organic solvents are cyclic amides, especially 2-pyrrolidone, N-methyl-pyrrolidone and N-ethyl-pyrrolidone; diols, especially I,5-pentane diol, ethyleneglycol, thiodiglycol, diethyleneglycol and triethyleneglycol; and mono-C14-alkyl and C14-alkyl ethers of diols, more preferably mono-C14-alkyl ethers of dials having 2 to 12 carbon atoms, especially 2-methoxy-2-ethoxy-2-ethoxyethanol.
Examples of further suitable liquid media comprising 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-A-425,150.
When the liquid medium comprises organic solvent free from water, (i.e. less than 1 % water by weight) the solvent preferably has a boiling point of from 30 to 200°C, more preferably of from 40 to 15000, 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 are any of the hereinbefore- described water-miscible organic solvents and mixtures thereof. Preferred water-immiscible solvents include, for example, aliphatic hydrocarbons; esters, preferably ethyl acetate; chlorinated hydrocarbons, preferably CH2CI2; and ethers, preferably diethyl ether; and mixtures thereof.
When the liquid medium comprises a water-immiscible organic solvent, preferably a polar solvent is included because this enhances solubility of the dyes in the liquid medium. Examples of polar solvents include C14-alcohols.
In view of the foregoing preferences it is especially preferred that where the liquid medium is organic solvent free from water it comprises a ketone (especially methyl ethyl ketone) and/or an alcohol (especially a C14-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 liquid medium is organic solvent free from water it is a mixture of 2 to 5 different organic solvents. This allows a liquid medium to be selected that gives good control over the drying characteristics and storage stability of the ink.
Liquid media comprising 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.
The liquid media may of course 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.
Although not usually necessary, further colorants may be added to the ink to modify the shade and performance properties. Examples of such colorants include 0.1. Direct Yellow 86, 132, 142 and 173; 0.1. Direct Blue 307; 0.1. Food Black 2; 0.1. Direct Black 168 and 195 and 0.1. Acid Yellow 23.
It is preferred that the composition according to the invention is ink suitable for use in an ink-jet printer. Ink suitable for use in an ink-jet printer is ink which is able to repeatedly fire through an ink-jet printing head without causing blockage of the fine nozzles. To do this the ink must be particle free, stable (i.e. not precipitate on storage), free from corrosive elements (e.g. chloride) and have a viscosity which allows for good droplet formation at the print head.
Ink suitable for use in an ink-jet printer preferably has a viscosity of less than 20 cP, more preferably less than 10 cP, especially less than 5 cP, at 25°C.
Ink suitable for use in an ink-jet printer preferably contains less than SOOppm, more preferably less than 2SOppm, especially less than lOOppm, more especially less than 1 Oppm in total of divalent and trivalent metal ions (other than any divalent and trivalent metal ions bound to a colorant of Formulae (1) to (8) or any other colourant or additive incorporated in the ink).
Preferably ink suitable for use in an ink-jet printer has been filtered through a filter having a mean pore size below 10pm, more preferably below 3pm, especially below 2pm, more especially below 1pm. This filtration removes particulate matter that could otherwise block the fine nozzles found in many ink-jet printers.
Preferably ink suitable for use in an ink-jet printer contains less than SOOppm, more preferably less than 2SOppm, especially less than lOOppm, more especially less than 1 Oppm in total of halide ions.
A third aspect of the invention provides a process for forming an image on a substrate comprising applying a composition, preferably ink suitable for use in an ink-jet printer, according to the second aspect of the invention, thereto by means of an ink-jet printer.
The ink-jet printer preferably applies the ink to the substrate in the form of droplets that are ejected through a small orifice onto the substrate. Preferred ink-jet printers are piezoelectric ink-jet printers and thermal ink-jet printers. In 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 from the orifice in the form of small droplets directed towards the substrate during relative movement between the substrate and the orifice. In piezoelectric ink-jet printers the oscillation of a small crystal causes ejection of the ink from the orifice.
Alternately the ink can be ejected by an electromechanical actuator connected to a moveable paddle or plunger, for example as described in International Patent Application W000/48938 and International Patent Application W000/55089.
The substrate is preferably paper, plastic, a textile, metal or glass, more preferably paper, an overhead projector slide or a textile material, especially paper.
Preferred papers are plain or treated papers which may have an acid, alkaline or neutral character. Glossy papers are especially preferred.
Photographic quality papers are especially preferred. Photographic quality paper are high-gloss papers which give a similar finish to that typically seen with silver halide photo printing.
A fourth aspect of the present invention provides a material preferably paper, plastic, a textile, metal or glass, more preferably paper, an overhead projector slide or a textile material, especially paper more especially plain, coated or treated papers printed with a compound as described in the first aspect of the invention, a composition according to the second aspect of the invention or by means of a process according to the third aspect of the invention.
It is especially preferred that the printed material of the fourth aspect of the invention is a print on a photographic quality paper printed using a process according to the third aspect of the invention.
A fifth aspect of the present invention provides an ink-jet printer cartridge comprising a chamber and a composition, preferably ink suitable for use in an ink-jet printer, wherein the composition is in the chamber and the composition is as defined and preferred in the second aspect of the present invention. The cartridge may contain a high concentration ink and a low concentration ink, as described in the second aspect of the invention, in different chambers.
The invention is further illustrated by the following Examples in which all parts and percentages are by weight unless otherwise stated.
Example 1
Preparation of: -CH3 cçp OSy L*o
OH
The dye of Example 1 may be prepared using a simple modification of the procedures as set out in W02002/O1 2402.
Example 2
Preparation of: cçç O HN.
CH2CH2SO3H The dye of Example 2 may be prepared using a simple modification of the procedures as set out in RU 2059610.
Example 3
Preparation of: OSy
OH
This compound may be prepared using processes which would be well known to one skilled in the art.
Example 4
Preparation of:
N N os SO3H
The dye of Example 4 may be prepared using a simple modification of the procedures as set out in US3707348.
Example 5
Preparation of:
N N oo1-o--o
The dye of Example 5 may be prepared using a simple modification of the procedures as set out in US3707348.
Example 6
Preparation of: HO.I1IJIIII1/? The dye of Example 6 may be prepared using a simple modification of the procedures as set out in W02002066450
Example 7
Preparation of compounds such as: H3C,o
N -
/_\ / 0 R-S 0 /_\ Compounds such as this may be prepared by reacting a bromo-substituted-anthrapyridone compound of Formula (B) BrI Formula (B) with a hydrocarbyl thiol.
Compounds such as those of Formula (B) may be prepared by reacting a compound such as that of Formula (C) with ethyl benzoyl acetate. H3C BrII\
Formula (C)
Example 8
Preparation of compounds such as: NC 0 (H
Q-
Compounds such as the above Formula, wherein Q is as defined above, may be prepared by reacting 1-substituted-amino anthraquinones of Formula (B) 0 \==/ Formula (B) with boron trifluoride diethyl etherate to give compounds of Formula (C):
Q-N
B-O \==/ Et Et Formula (C) The compounds of Formula (C) may then be reacted with malononitrile to give the title compounds Preparation of Inks Ink may be prepared by dissolving 3g of a dye such as that described in Example 1 in 97 ml of a liquid medium consisting of 7 parts 2-pyrrolidone; 7 parts diethylene glycol; 7 parts ethylene glycol; 1 part Sur{ynolRTM 465; 0.2 parts Tris buffer and the balance deionised water and adjusting the pH to between pH 8 to 8.5 with sodium hydroxide. Sur{ynolRTM 465 is a surtactant from Air Products.
Ink-iet Printinci Ink prepared as described above may be filtered through a 0.45 micron nylon filter and then incorporated into empty print cartridges using a syringe.
This ink may be printed on to plain paper or a specialised ink-jet media.
Prints, formed by ink-jet printing, may be tested for ozone fastness by exposure to Sppm ozone at 25°C, 50% relative humidity, for 24 hours in a Hampden 903 Ozone cabinet. Fastness of the printed ink to ozone can be judged by the difference in the optical density before and after exposure to ozone.
Light-fastness of the printed image may be assessed by fading the printed image in an Atlas Ci5000 Weatherometer for 100 hours and then measuring the change in the optical density. (RTM) Optical density measurements can be performed using a Gretag spectrolino spectrophotometer set to the following parameters: Measuring Geometry: 0°/45° Spectral Range: 380 -730nm Spectral Interval: lOnm Illuminant: D65 Observer: 2° (OlE 1931) Density: Ansi A External Filler: None Light and Ozone fastness may then be assessed by the percentage change in the optical density of the print, where a lower figure indicates higher fastness, and the degree of fade. The degree of fade is expressed as AE where a lower figure indicates higher light fastness. AE is defined as the overall change in the OlE colour co-ordinates L, a, b of the print and is expressed by the equation AE = (AL2 + A a2 + Ab2)°5.
Bronzing of the printed image may be conveniently assessed visually using an arbitrary scale of 0 (no bronzing) to 10 (heavy bronzing).
Further Inks The inks described in Tables A and B may be prepared using the compound of Example 1. The dye indicated in the first column is dissolved in 100 parts of the ink as specified in the second column on. Numbers quoted in the second column onwards refer to the number of parts of the relevant ink ingredient and all parts are by weight. The pH of the ink may be adjusted using a suitable acid or base. The inks may be applied to a substrate by ink-jet printing.
The following abbreviations are used in Tables A and B: PG = propylene glycol DEG = diethylene glycol NMP = N-methyl pyrrolidone DMK = dimethylketone IPA = isopropanol 2P = 2-pyrrolidone MIBK = methylisobutyl ketone P12 = propane-i,2-diol BDL = butane-2,3-diol TBT = tertiary butanol
TABLE A
Dye Water PG DEG NMP DMK IPA 2P MIBK 2.0 80 5 6 4 5 3.0 90 5 5 10.0 85 3 3 3 6 2.1 91 8 1 3.1 86 5 4 5 1.1 81 9 10 2.5 60 4 15 3 3 6 5 4 65 20 10 5 2.4 75 5 10 5 5 4.1 80 3 5 2 10 3.2 65 5 4 6 5 10 5 5.1 96 4 10.8 90 5 5 10.0 80 2 6 2 5 1 4 1.8 80 5 15 2.6 84 11 5 3.3 80 4 10 6 12.0 90 7 3 5.4 69 2 20 2 1 3 3 6.0 91 ____ ______ 4 _____ _____ 5 _____
TABLE B
Dye Water PG DEG NMP TBT BDL P12 Content _______ ____ ______ ______ ______ ______ _____ 3.0 80 20 9.0 90 5 5 1.5 85 5 5 5 2.5 90 6 4 3.1 82 4 8 6 0.9 85 10 5 8.0 90 5 5 4.0 70 10 4 5 11 2.2 75 10 10 3 2 10.0 91 9 9.0 76 9 7 3 5 5.0 78 5 11 6 5.4 86 7 7 2.1 70 5 10 5 5 5 2.0 90 10 2 88 12 78 5 7 10 8 70 2 20 8 80 10 10 80 ____ 20 _____ _____ _____ ____

Claims (6)

  1. CLAIMS1. Compounds of Formulae (1) to (8) and salts thereof: R3)N-R (R1) o S Formula (1) wherein: R2 is an optionally substituted hydrocarbyl group; R4 is optionally substituted aryl, optionally substituted heterocyclyl or n is 0 to 4; wherein the compound of Formula (1) carries at least one substituent selected from the group consisting of-503H, -CO2H, -COSH or -P03H2; R3)N-R (R1) o NH R5 Formula (2) wherein: R5 is optionally substituted alkyl; R6 is optionally substituted aryl or optionally substituted heteroaryl; n is 0 to 4; and wherein the compound of Formula (2) carries at least one substituent selected from the group consisting of-503H, -CO2H, -COSH or -P03H2;-z X(R1) ItIIIIIJII o A Formula (3) wherein: R is an optionally substituted hydrocarbyl group; A is S, 0 or NR7; R7 is H, optionally substituted alkyl, optionally substituted aryl or optionally n is 0 to 4; one of X, Y and Z is -S-; one of X, Y and Z is -C(=0)-; and one of X, Y and Z is optionally substituted carbon: and wherein the compound of Formula (3) carries at least one substituent selected from the group consisting of -SO3H, -CO2H, -.COSH or -P03H2; x2NN (R1) o SFormula (4) wherein: R2 is an optionally substituted hydrocarbyl group; X2 is H, optionally substituted alkyl, optionally substituted aryl or optionally n is 0 to 4; and provided that the compound of Formula (4) carries at least one substituent selected from the group consisting of -SO3H, -CO2H, -.COSH and -P03H2; x2NN(R1) IIIItiIIIIJiE ° Formula (5) wherein: R is an optionally substituted hydrocarbyl group; X2 is H, optionally substituted alkyl, optionally substituted aryl or optionally n is 0 to 4; and provided that (i) the compound of Formula (5) carries at least one substituent selected from the group consisting of-SO3H, -CO2H, -COSH and -P03H2; and (ii) X2 and R2 are not both phenyl; (R8) o A Formula (6) wherein: R8 is -SO3H, -CO2H, -COSH or -P03H2, halo, nitro, cyano, CORd, CONRdRe, SO2NRdRe or SO2Rd where Rd and Re are each independently H, optionally substituted alkyl or optionally substituted aryl; R2 is an optionally substituted hydrocarbyl group; AisS,00rNR7; R7 is H, optionally substituted alkyl, optionally substituted aryl or optionally n is 0 to 4; X3 and Y2 together with the anthrone ring to which they are attached form a 5-membered optionally substituted fused heterocyclic ring system wherein one of X3 and Y2 is N and the other is 0, S or optionally substituted carbon: wherein the compound of Formula (6) carries at least one substituent selected from the group consisting of is -SO3H, -CO2H, -COSH or -P03H2; and provided that the compound of Formula (6) is not of Formula (a) or a salt thereof N-: HO2C Formula (a); x4 (R1) 0 A. 2R
    Formula (7) wherein: R2 is an optionally substituted hydrocarbyl group; AisSorO; n is 0 to 4; one of X4, Y3 and Z2 is -NR3-; one of X, Y and Z is -C(=O)-; and one of X4, Y3 and Z2 is optionally substituted carbon; and (R1) Formula (8) wherein: R2 is an optionally substituted hydrocarbyl group; R7 is H, optionally substituted alkyl, optionally substituted aryl or optionally n is 0 to 4; one of X5, Y4 and Z3 is -NR4-; one of X5, Y4 and Z3 is -C(=O)-; and one of X5, Y4 and Z3 is carbon carrying an optionally substituted aryl or ON; and R1° is optionally substituted alkyl, optionally substituted aryl or optionally
  2. 2. A composition comprising a compound of Formulae (1) to (8) and/or a salt thereof, as described in claim 1 and a liquid medium.
  3. 3. A composition as claimed in claim 2 which is ink suitable for use in an ink-jet printer.
  4. 4. A process for forming an image on a substrate comprising applying ink suitable for use in an ink-jet printer, according to claim 3, thereto by means of an ink-jet printer.
  5. 5. A material printed with a compound as described in claim 1.
  6. 6. An ink-jet printer cartridge comprising a chamber and ink suitable for use in an ink-jet printer, according to claim 3, wherein the ink is in the chamber.
GB0917208A 2008-10-11 2009-10-01 Dyes and inks suitable for use in ink jet printing Withdrawn GB2464188A (en)

Applications Claiming Priority (8)

Application Number Priority Date Filing Date Title
GB0818703A GB0818703D0 (en) 2008-10-11 2008-10-11 Magenta dyes and inks for use in ink-jet printing
GB0818708A GB0818708D0 (en) 2008-10-11 2008-10-11 Magenta dyes and inks for use in ink-jet printing
GB0818706A GB0818706D0 (en) 2008-10-11 2008-10-11 Magenta dyes and inks for use in ink-jet printing
GB0818709A GB0818709D0 (en) 2008-10-11 2008-10-11 Magenta dyes and inks for use in ink-jet printing
GB0818710A GB0818710D0 (en) 2008-10-11 2008-10-11 Magenta dyes and inks for use in ink-jet printing
GB0818707A GB0818707D0 (en) 2008-10-11 2008-10-11 Magenta dyes and inks for use in ink-jet printing
GB0818704A GB0818704D0 (en) 2008-10-11 2008-10-11 Magenta dyes and inks for use in ink-jet printing
GB0818705A GB0818705D0 (en) 2008-10-11 2008-10-11 Magenta dyes and inks for use in ink-jet printing

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012094820A1 (en) 2011-01-14 2012-07-19 大连理工大学 Anthrapyridone sulphonic acid compounds, preparation and use thereof
WO2013029260A1 (en) 2011-09-01 2013-03-07 大连理工大学 Carbonylpropylsulfonyl anthracene pyridone sulfonic acid compound and preparation method and use thereof
CN107068911A (en) * 2016-04-25 2017-08-18 中节能万润股份有限公司 A kind of organic electroluminescence device containing anthracene ketone compounds and its application

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002012402A2 (en) * 2000-08-07 2002-02-14 Eastman Chemical Company Colorant compounds containing copolymerizable vinyl groups
WO2008066024A1 (en) * 2006-11-29 2008-06-05 Nippon Kayaku Kabushiki Kaisha Anthrapyridone compound, salt thereof, magenta ink composition and colored body

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002012402A2 (en) * 2000-08-07 2002-02-14 Eastman Chemical Company Colorant compounds containing copolymerizable vinyl groups
WO2008066024A1 (en) * 2006-11-29 2008-06-05 Nippon Kayaku Kabushiki Kaisha Anthrapyridone compound, salt thereof, magenta ink composition and colored body

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012094820A1 (en) 2011-01-14 2012-07-19 大连理工大学 Anthrapyridone sulphonic acid compounds, preparation and use thereof
WO2013029260A1 (en) 2011-09-01 2013-03-07 大连理工大学 Carbonylpropylsulfonyl anthracene pyridone sulfonic acid compound and preparation method and use thereof
US8734580B2 (en) 2011-09-01 2014-05-27 Dalian University Of Technology Carbonyl propyl sulfuryl anthrapyridone sulfonic acid compounds and their preparation methods and applications
CN107068911A (en) * 2016-04-25 2017-08-18 中节能万润股份有限公司 A kind of organic electroluminescence device containing anthracene ketone compounds and its application
CN107068911B (en) * 2016-04-25 2019-05-14 中节能万润股份有限公司 A kind of organic electroluminescence device containing anthracene ketone compounds and its application

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