GB2340839A - 8-aroylamino-2-[(carboxyaryl)azo]-1-hydroxy-naphthalene-disulphonic acid dyes for use in ink jet inks - Google Patents

8-aroylamino-2-[(carboxyaryl)azo]-1-hydroxy-naphthalene-disulphonic acid dyes for use in ink jet inks Download PDF

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GB2340839A
GB2340839A GB9919873A GB9919873A GB2340839A GB 2340839 A GB2340839 A GB 2340839A GB 9919873 A GB9919873 A GB 9919873A GB 9919873 A GB9919873 A GB 9919873A GB 2340839 A GB2340839 A GB 2340839A
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formula
ink
ink jet
water
optionally substituted
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GB9919873D0 (en
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Paul Wight
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Avecia Ltd
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Avecia Ltd
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    • 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
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/24—Monoazo dyes prepared by diazotising and coupling from coupling components containing both hydroxyl and amino directing groups
    • C09B29/28—Amino naphthols
    • C09B29/30—Amino naphtholsulfonic acid

Abstract

Compounds of Formula (1) having one or more azo groups and salts thereof: <EMI ID=1.1 HE=43 WI=49 LX=782 LY=562 TI=CF> <PC>[wherein: <DL TSIZE=4> <DT>Ar<SP>1</SP><DD>is substituted aryl (especially phenyl and napthyl) wherein at least one substituent is -COOH; <DT>R<SP>1</SP><DD>is H or optionally substituted alkyl; <DT>L<DD>is substituted phenyl carrying at least one substituent at the 2- position, or optionally substituted naphthy] are disclosed. </DL> Also disclosed are compositions comprising a compound of the Formula (1) and a water-soluble magenta dye; liquid compositions, especially inks and coloured concentrates, containing a compound of Formula (1 ); an ink jet printing process using the inks, substrates printed with the inks, and an ink jet printer cartridge and an ink jet printer containing the inks.

Description

2340839 COMPOUNDS This invention relates to dyes, to inks, to compositions
and to their use in ink jet printing (%P"). 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.
There are many demanding performance requirements for dyes and inks used in UP. For example they desirably provide sharp, non-feathered images having good water-fastness, light-fastness and optical density. 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.
According to the present invention there is provided a compound of Formula (1) and salts thereof:
0 W\ A, Arl---N OH N L N "5, N H03S S03H is Formula (1) wherein:
Ar' is substituted aryl carrying at least one -COOH group; R' is H or optionally substituted alkyl; L is substituted phenyl carrying at least one substituent at the 2- position, or optionally substituted naphthyl.
Preferably the compound of Formula (1) is a mono-azo compound (i.e. it contains only one -N=W group).
Preferably R' is H or optionally substituted Cl_.-alkyl, more preferably H or Cl,-alkyi optionally substituted by -OH, -COOH, -S03H or -CM It is especially preferred that R'is methyl, ethyl or H, more especially H.
Ar' is preferably substituted naphthyl or, more preferably, substituted phenyl, wherein at least one of the substituents is -COOH. It is especially preferred that Ar' is a group of the Formula (2):
P 1 2 (HOOC),,,,,9_ (13)p Formula (2) wherein:
each B independently is a substituent other than H; p is 0 to 4; n is 1 or 2; and (n+p) is 5 or less.
Preferably each B independently 'S -S03H, -PO3H2, -CF3, optionally substituted alkoxy, optionally substituted alkyl, optionally substituted amino, halo, -CN, -OH, -N02 or -SO2W; wherein W is optionally substituted alkyl (preferably optionally substituted Cl-1. -alkyl), optionally substituted aryl (preferably optionally substituted phenyl), - NIRIR 3, vinyl or a group convertible to vinyl on treatment with aqueous alkali; and R 2 and R3 are each independently H, optionally substituted alkyl or optionally is substituted aryi, or R 2 and R 3 together with the nitrogen to which they are attached form an optionally substituted piperaziny], morpholinyl or piperidinyl ring.
Preferably R 2 and R' are each independently H, optionally substituted C, 10-alkyl or optionally substituted phenyl, more preferably H, optionally substituted Cl-6-alkyl or optionally substituted phenyl.
When W is a group which is convertible to vinyl on treatment with aqueous alkali it is preferably of the formula -CH2CH20SO3H, -CH2CH2SS0,1-1, -CH2CH2C1 or -CH2CH20COCH, Preferably W is -NR 2 R', -CH=CH2or -CH2CH2OS0,1-1 and especially -CH=CH2 or -NR 2 R 3, wherein R 2 and R 3 are as hereinbefore defined.
In a preferred embodiment each B independently is -S031-1, -P031-12, -CF3, optionally substituted C1.10-alkoxy, optionally substituted Cl,,-alkyl, optionally substituted amino, -F 2 3 -Cl, -Br, -CN, -OH, -N02 or -S02NIR R, wherein R2 and R3 are as hereinbefore defined.
When B, R 2 or R 3 is substituted the substituent(s) islare preferably selected from Cl-,-alkyl, C,-hydroxyalkyl, Cl,-alkoxy, C,-4-alkylCO, -OH, -S03H, -COOH, -P031-12, halo and -NH2.
It is especially preferred that each B independently 'S -S03H, -CF3, -NH2, halo, -NI-ICOC,-4-alkyl (preferably -NHCOCH3), C,,,,-alkoxy, -S02NHC,,-alkyl, -S02NHC,,-hydroxyalkyl or Cl-a-alkyl optionally substituted by -OH, -COOH, -NH2 or -S03H.
When Ar' is a group of the Formula (2), preferably p = 0 and n = 1 or 2. It is especially preferred that p=O, n=l and that the -COOH group is attached ortho to the azo group shown in Formula (1).
3 When Ar' is substituted naphthyl it is preferably substituted by one COOH and optionally one or more of the hereinbefore defined groups B. This -COOH group is preferably attached ortho to the azo group shown in Formula (1). An especially preferred substituted naphthyl group represented by Ar' is an optionally substituted 1 -carboxy-naphth-2-yi group.
Preferably L is of the Formula (3) or (4):
X G_ (T), M11 Formula (3) Formula (4) wherein:
X and each T independently is a substituent other than H; m is 0 to 4; and q is 0 to 7.
Preferably q is 0 to 3, more preferably 0 or 1 and especially 0. m is preferably 0 or 1, more preferably 0.
Preferably X and each T independently are selected from the preferred groups described above for B or COOH, more preferably a group B as hereinbefore defined.
It is especially preferred that each T independently 'S -S03H, -CF3, -NH2, halo, -NI-ICOC,-alkyl (preferably -NHCOCH3), C,,-alkoxy, -S02NHC,,-alkyl, -S02NHC,,-hydroxyalkyl or C,,-alkyl optionally substituted by -OH, -COOH, -NH2 or -S03H.
It is especially preferred that X 'S -S03H, -CF3, -NH2, halo, C,-6-alkoxy or C,,,-alkyl optionally substituted by -OH, -COOH, -NH2 or -S03H. More especially X is C,-alkyl, Cl-4-alkoxy, -Cl, -Br or -OH, particularly methyl or -Cl.
When L is of the Formula (4), the naphthyl group is preferably attached at the 1-, or more preferably 2- position to the carbonyl group shown in Formula (1).
It is especially preferred that L is of the Formula (3), wherein m=0.
The floating sulpho group shown in Formula (1) is preferably attached meta to the -NR'- group.
In view of the foregoing preferences, a preferred compound according to the first aspect of the present invention is of the Formula (5) or a salt thereof:
J 4 0 xl 4 R,,, OH N HOOC H S S03H Formula (5) wherein:
xl is -S03H, -CF3, -NH2, halo, Cl,,,-alkoxy or Cl,.-alkyl optionally substituted by -OH, -COOH, -NH2 or -S03H; and R 4 is H or Cl-4-alkyl optionally substituted by -OH, -COOH or -S03H.
X' is preferably halo (especially F, Cl or Br), Cl-6-alkyl or -S03H, more preferably C,-alkyl, C,,-alkoxy, -S03H, -Cl or Br, particularly C,-4-alkyl, -Cl or - S03H and especially -Cl or -S03H.
The -COOH group shown in Formula (5) is preferably attached ortho to the azo group.
Especially preferred compounds of the Formula (5) are those in which the COOH group is attached ortho to the azo group; R 4 is H or C,-alky]; and X' is -Cl, C,,-alkyl (especially methyl or ethyl) or -S03H.
is The compounds of the invention exhibit a high solubility in aqueous media and provide prints which exhibit good light-fastness and chroma when incorporated into inks for ink jet printing. We have found that the presence of the substituent X in Formula (3) and X' in Formula (5) provides compounds with a particularly high light- fastness.
The compounds of the invention may be in the free acid or salt form. Preferred salts are water-soluble, for example alkali metal salts, especially lithium, sodium and potassium salts, ammonium and substituted ammonium salts. Especially preferred salts are salts with sodium, lithium, ammonia and volatile amines. The compounds may be converted into a salt using known techniques. For example, an alkali metal salt may be converted into a salt with ammonia or an amine by dissolving an alkali metal salt in water, acidifying with a mineral acid, adjusting the pH of the solution to pH 9 to 9.5 with ammonia or the amine and removing the alkali metal cations by dialysis, reverse osmosis or ultrafiltration.
The compounds of the invention may be prepared using conventional techniques for the preparation of azo dyes. For example a suitable method comprises coupling the diazonium salt of an amine of the formula Ar'N1-12 with a compound of the Formula (6), preferably under mildly alkaline reaction conditions:
1 0 R\ OH NA L I HO 3S S03H Formula (6) wherein, L, Ar' and R' are as hereinbefore defined.
The coupling reaction is preferably performed in a liquid medium, more preferably an aqueous medium and especially water. A reaction temperature in the range of from -50C to 2011C is preferred, more preferably from 0 to 10"C. Preferably a reaction time of I to 48, more preferably 3 to 24 hours is used.
The coupling reaction is preferably performed in the presence of a base. The base may be any inorganic base for example, ammonia, an alkali metal or alkali earth metal hydroxide, carbonate or bicarbonate, or an organic base. Preferred organic bases are tertiary amines for example, N-alkylated heterocycles, for example N-(C,,-alkyl)morpholine, N-(C,,-alkyl)piperidine, N,N'-di(C,,- alkyl)piperazine; tri(C,,-alkyl)amines, for example triethylamine, and optionally substituted pyridines, especially pyridine.
The amount of base used may be varied between wide limits but it is preferred to use less than 40, more preferably less than 10 and especially from 3 to 5 moles for each mole of the compound of Formula (6).
After the coupling reaction the product may be isolated by precipitating the product as a salt from the reaction mixture for example by the addition of a suitable alkali metal salt, especially sodium chloride. Alternatively, the product may be isolated in its free acid form by acidifying the reaction mixture, preferably using a mineral acid, especially hydrochloric acid. Where the product precipitates as a solid it may be separated from the mixture by filtration.
If desired unwanted anions may be removed from the product of the above process by dialysis, osmosis, ultrafiltration or a combination thereof.
The diazotisation of the amine of the formula ArNH2 is preferably performed in an aqueous medium at a pH below 7 in the presence of a suitable diazotisation agent. Dilute mineral acid, e.g. HCl or H2SO4, is preferably used to achieve the desired acidic conditions. Conveniently the diazotisation agent is formed in-situ, for example by dissolving an alkali metal nitrite, preferably sodium nitrite, in a molar excess of mineral acid, preferably HC1. Normally at least one mole of diazotisation agent per mole of the compound of formula Ar'-NH2, preferably from 1 to 1.25 moles, will be used in the diazotisation.
The temperature of the diazotisation is not critical and may conveniently be carried out at from -50C to 200C, preferably from 0 to I OOC and especially from 0 to 50C.
6 The compound of the Formula (6) may be prepared using conventional techniques, for example by condensing a compound of the Formula LC(O)C1 with a compound of the Formula (7):
R\ OH NH HO 3si 4 S03H Formula (7) wherein L and R' are as hereinbefore defined.
The compounds of Formula (1) may exist in tautomeric forms other than those shown in this specification, for example the hydrazo tautomer. These tautomers are included within the scope of the present claims.
The present invention also covers mixtures comprising two or more dyes of the Formula (1).
According to a second aspect of the present invention there is provided a composition comprising:
is (a) one or more compound according to the first aspect of the present invention; and (b) one or more water-solubie magenta dye other than a compound according to the first aspect of the invention.
The water-soluble magenta dye is preferably a xanthene dye, or an azo or bis azo dye, more preferably an anionic azo or bis azo dye and especially an azo or bis azo dye which contains one or more groups selected from sulphonate, carboxylate and thiocarboxylate groups.
Preferred water-soluble magenta dyes include C.I. Acid Red 50, 52, 87, 91, 92, 95, 249 and 289; CI Direct Violet 106 and 107; compounds 100 to 107, 200 and 201 described on pages 8 and 9 of W096124636; compounds 1 to 24 shown described on cols. 4 to 10 in US 5,542,970; compounds 1 to 55 described on pages 7 to 17 of EP-A-682 088; compounds 1 to 14 shown in Example 1 to 6 of EP-A-194,885; compounds 1 to 24 described on pages 8 to 13 of EP-A-717 089; the compounds described in examples 1 to 16 in cots 5 to 11 of US 5,262,527; the dyes described in Examples 1 to 21 in WO 94116021; and one or more dyes of the Formula (8) and salts thereof:
7 B 1 RS z 1 NH2 N IN N-- N N A OH H03S Q H03S 0 H N,x A A N N -,\ NH2 1 ' N-2 P-/ - R B 2 z Formula (8) wherein:
B' and B 2 are, each independently, -S03H, -COOH, -CF3, alkoxy, alkyl or P03H2; Q is an organic linking group; Rsand R' are, each independently, H or optionally substituted alkyl; each A independently is N, C-Ci, C-CN or C-N02; Z' and Z2 are, each independently, -SR', -OR', -NR'R" or halogen; R 7, R", R9 & W0 are, each independently, H, optionally substituted alkyl, optionally substituted aryl or optionally substituted aralkyl; or R' and W0 together with the nitrogen to which they are attached, form an optionally substituted five or six membered ring; Especially preferred water-soluble magenta dyes for use in the composition is according to the second aspect of the invention include C.I. Acid Red 52, C.I. Acid Red 289 or a dye of the Formula (9), (10) or (11), or a salt of any of the foregoing:
-NH S03H OH NH--/ N N=N_ CH2b H03S S03H -NH 03H L 2 Formula (9) 8 COOH OH HOOC"" N=N OH NH-/ N N /r__H3 S03H N N- 1-103S)6 ' JC2H Formula (10) NH2 H03 N,, H CH2CH20H OH NI/ N H03S HO.SCH2C1-12NH --N CH2CH20H Formula (11) The dye of Formula (9) may be prepared using the method described in Example 1 of EP 0 559 310. The dye of the Formula (10) may be prepared using the method described in Example 3 of PCT publication number WO 94116021. The dye of Formula (11) may be prepared using the method described in Example 1 of WO 96124636.
The composition according to the second aspect of the present invention preferably comprises:
(a) from 1 to 99, more preferably from 3 to 70 and especially from 5 to 50 parts in total of the compound(s) according to the first aspect of the invention; and (b) from 99 to 1, more preferably from 30 to 97 parts and especially 95 to 50 parts in is total of the water-soluble magenta dye(s); wherein the parts are by weight and the sum of the parts (a) and (b) = 100 The composition may contain a single dye of Formula (1) or a mixture thereof.
Similarly, the composition may contain a single water-soluble magenta dye or a mixture of two or more water-soluble magenta dyes.
According to a third aspect of the present invention there is provided a liquid composition comprising:
(a) a compound according to the first aspect of the present invention, or a composition according to the second aspect of the invention; and (b) a liquid medium.
Preferred compounds comprising component (a) of the liquid composition are the preferred compounds according to the first aspect of the invention, more preferably one or 1 more compounds of the Formula (1) or Formula (5), as hereinbefore defined.
9 The liquid medium is preferably a low melting point solid, water, a mixture of water and an organic solvent or an organic solvent. More preferably the medium comprises (i), (ii) or (iii):
(i) a mixture of water and an organic solvent; (ii) an organic solvent free from water; or (iii) a low melting point solid.
The number of parts by weight of component (a) of the liquid composition is preferably from 0.01 to 30, more preferably 0.1 to 20, especially from 0. 5 to 15, and more especially from 1 to 5 parts. The number of parts by weight of component (b) is preferably from 99.99 to 70, more preferably from 99.9 to 80, especially from 99.5 to 85,and more especially from 99 to 95 parts. The number of parts (a) + (b) is preferably 100.
When the medium is a mixture of water and an organic solvent or an organic solvent free from water, preferably component (a) is completely dissolved in component (b). Preferably component (a) has a solubility in component (b) at 200C of at least 10%.
This allows the preparation of concentrates which may be used to prepare more dilute compositions and inks and reduces the chance of the compound(s) of component (a) of the composition precipitating if evaporation of the liquid medium occurs during storage.
When the medium comprises a mixture of water and an 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 Cl.,,-alkanols, preferably methanol, ethanol, n-propanol, isopropanol, n-butanol, sec-butanol, tert-butanol, n-pentanol, cyclopentanol and cyclohexanol; linear amides, preferably dimethy1formamide 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-hexanetdol; mono-C,,-alkyl ethers of diols, preferably mono-C,,- 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]-ethanoI and ethyleneglycol monoallylether; cyclic amides, preferably 2-pyrrolidone, N-methyl-2-pyrrolidone, N-ethyl-2-pyrrolidone, caprolactarn and 1,3-dimethylimidazolidone; cyclic esters, preferably caprolactone; sulphoxides, preferably dimethyl sulphoxide and sulpholane. Preferably the liquid medium comprises water and 2 or more, especially from 2 to 8, water-miscible organic solvents.
The liquid compositions according to this aspect of the invention are particularly useful as an ink or a coloured concentrate which may be used to prepare an ink. When the liquid composition is used as a coloured concentrate to prepare an ink, the ink is preferably prepared by diluting the coloured concentrate with a suitable liquid medium, preferably one of the hereinbefore described liquid media. It is preferred however, that the liquid composition according to the third aspect of the invention is an ink, more preferably an ink jet printing ink.
Examples of further suitable ink 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, EP 425,150A and US 5,207,824.
When the liquid medium comprises an organic solvent free from water, (i.e. less than 1 % water by weight) the solvent preferably has a boiling point of from 300 to 2000C, more preferably of from 401 to 1501C, especially from 50 to 1250C. The organic solvent may be water-immiscible, water-miscible or a mixture of such solvents. Preferred is water-miscible organic solvents are any of the hereinbefore described water-miscibie organic solvents and mixtures thereof. Preferred water-immiscible solvents include, for example, aliphatic hydrocarbons; esters, preferably ethyl acetate; chlorinated hydrocarbons, preferably CH2C12; 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 component (a) of the composition in the liquid medium. Examples of polar solvents include Cl,- alcohols. In view of the foregoing preferences it is especially preferred that where the liquid medium is an organic solvent free from water it comprises a ketone (especially methyl ethyl ketone) Wor an alcohol (especially a Cl,-alkanol, such as 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. This is particularly so when the liquid composition is used as an ink, especially an ink jet printing 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 60C to 125'C. Suitable low melting point solids include long chain fatty acids or alcohols, preferably those withC,,-24 chains, and sulphonamides. The compound of Formula (1) or Formula (3) may be dissolved in the low melting point solid or may be finely dispersed in it.
The compounds according to the present invention exhibit a high solubility in aqueous media, accordingly it is preferred that the liquid medium is a mixture of water and one or more water miscible organic solvent(s). An especially preferred liquid composition which is suitable for use as an ink for an ink jet printer comprises:
(a) from 1 to 10 parts in total of a compound or composition according to the first or second aspect of the invention; (b) from 2 to 60, more preferably 5 to 40 parts of water-soluble organic solvent; and (c) from 30 to 97, more preferably 40 to 85 parts water; wherein all parts are by weight and the sum of the parts (a) + (b) + (c) = 100.
The liquid compositions according to this third aspect of the invention 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, anti-cockle agents to reduce paper curling and surfactants which may be ionic or non-ionic.
The pH of the liquid composition is preferably from 4 to 10.
The compounds, compositions and liquid compositions according to the first and second aspects of the present invention may be, and preferably are, purified to remove undesirable impurities before they are incorporated into inks for ink jet printing.
Conventional purification techniques may be employed, for example ultrafiltration, reverse osmosis, dialysis or a combination thereof.
The liquid composition according to the third aspect of the invention preferably have a concentration of less than 100 parts per million, more preferably less than 50 parts per million, in total of undesirable ions, for example halide ions, silicon ions, peroxide radicals and divalent and trivalent metals, especially calcium ions. Such liquid compositions are particularly well suited to use as ink jet printing inks because higher levels of undesirable ions could lead to printing problems, especially in thermal ink jet printing heads.
A fourth aspect of the present invention provides a process for printing an image on a substrate comprising applying thereto by means of an ink jet printer an ink containing a compound according to the first aspect of the invention or a composition according to the second aspect of the invention.
The ink used in this process is preferably a liquid composition according to the third aspect of the present invention.
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. In thermal ink jet pirinters, 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 during relative movement between the substrate and the 12 orifice. In piezoelectric ink jet printers the oscillation of a small crystal causes ejection of the ink from the orifice.
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, P1kaline or WTI") neutral character.
,amples of commercially available papers include, HPPremium Coated Paper, HPIPhotopaper (all available from Hewlett Packard Inc), Stylus Pro 720 (pro%) cen-4 dpi Coated Paper, EpsonPhoto Quality Gl?p Film, EpsonJPh6to Quality Glossy Paper IRT. (RT;., (available from Seiko Epson Qorp.), CanonjHR 101 High Resolution Paper, Canon/GP 201 Glossy Paper CanonrHO 101 High Gloss Film (all available flom, Canon Inc.), Vie,) (Rr- I Wiggins Conqueroripaper (available from Wiggins Teape Ltd), Xerox4Acid Paper and XeroxAlkaline paper, Xero)Acid Paper (available from Xerox).
A fifth aspect of the present invention provides a substrate, preferably a paper, an overhead projector slide or a textile material, printed with a liquid composition according to the third aspect of the present invention or by means of the process according to the fourth aspect of the present invention.
According to a sixth aspect of the present invention there is provided an ink jet printer cartridge comprising a chamber and ink, wherein the ink is present in the chamber and the ink contains a compound or a composition according to the first or second aspect of the invention. Preferably the ink is a liquid composition according to the third aspect of the invention.
According to a seventh aspect of the present invention there is provided an ink jet printer containing an ink jet printer cartridge, wherein the ink jet printer cartridge is as defined in the sixth aspect of the present invention.
The invention is further illustrated by the following Examples in which all parts and percentages are by weight unless otherwise stated.
ExamaLe 1 Dye (1) ci 0 OH HN HOOC N=N I I-1Z H03S.105S03H Dye (1) Dye 1 was prepared in accordance with following process:
13 Stage (a): Diazotisation Anthranilic acid (7.0g, 0.05 moles) was dissolved in water (10Omls) and concentrated hydrochloric acid (20mis). The solution was cooled to 0-50C and sodium nitrite (4.0g, 0.06 moles) was added in small portions. The solution was stirred a further 1.5 hours at 0-51C, then the excess nitrous acid destroyed by the addition of saturated suiphamic acid solution.
Stage (b): Coupling 2-chlorobenzoyl H acid (28.6g at 76%, 0.05 moles) was suspended in water (200mis) and dissolved by the addition of 2M sodium hydroxide to pH 7.5. The solution was screened and then added to the product of stage (a) over 10 minutes at 0-50C. The mixture was stirred for 1 hour at 0-50C then allowed to rise to ambient and stirred a further 2 hours. The product was filtered off and washed with 10% brine (2 x 100mis), then saturated brine (500mis). The title product was washed with acetone (300mis) and then oven dried at 501C.
Example 2
Dye 2 0 OH HN-b HOOC N=N H03S SO3H Dye (2) Dye (2) was prepared using the same method described above for the preparation of Dye (1), except the 2-chlorobenzoyl chloride used in Example 1 was replaced with 2-methyibenzoyl chloride.
Example 3 Inks and Ink Jet Printinci Ink An ink comprising 3 parts of Dye (1) from Example 1 and 97 parts of an ink medium comprising:
10 parts butyl CarbitoITM [2-(2-b utyoxyethoxy)etha n oil; parts glycerol; 1 part Surfynol' 465 (a non-ionic surfactant available from Air Products Inc.); 79 parts water 14 was prepared by dissolving Dye (1) is the medium and filtering the resultant ink through a 0.45lam filter.
Ink Jet Printin-q (ierm The ink was loaded into an Seiko EpsonStylus Colour Pro ink jet printer and was ink jet printed onto each of the substrates shown in column 1 of Table 1. The resulting prints were a bright magenta shade with a high water- fastness. The prints exhibited the reflected optical density shown under "ROW in Table 1, as measured using an X-Rite TM 938 Spectrodensitometer.
The light-fastness of each print was assessed by exposing a portion ofeach print to 50 hours fading in an Atlas Ci-35a Weatherometer and measuring the colour difference (AE) between the faded and un-faded portions of the print using an X-Rite TM Spectrodensitometer. The measured AE values are shown in column 3 of Table 1. A small AE value corresponds to a small colour difference and hence a high light-fastness.
is Table 1
Substrate ROD AE (after 50 hours) X. Acid 1.002 4.15 S. Coated 1.094 3.85 S Glossy Paper 1.54 10-41 Glossy Film 1.665 8.19 In Table 1 the following abbr%iat' 4 )ons are used:
X. Acid XeroxAcid aper (, 'I S. Coated Seiko EpsoryCoated paper (am) S. Glossy Paper Seiko Epson)Glossy paper (R?.-) S. Glossy Film Seiko Epson klossy Film rli 1.1 Example 4
Further dyes of Formula (A) may be prepared using the same method described for the preparation of Dye (1), except in place of the 2-chlorobenzoyl chloride used in Example 1 there is used the benzoyl chloride shown in Table 2.
Table 2
Dye Benzoyl Chloride Dye (3) C' cl 0 0 111 Dye (4) cl cl - 0 )/,--0 cl Dye (5) C, CH30 _b 0 Dye (6) C,;b 0, Dye (7) H3C cl - /I- CH3 0 H3C Dye (8) C, F /I- F 0 Example 5
The inks described in Tables 3, 4, 5 and 6 may be prepared wherein the Dye described in the first column is the Dye described in the above Examples. 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.
The following abbreviations are used in Tables 3, 4, 5 and 6:
PG = propylene glycol DEG = diethylene glycol NMP = N-methyl pyrrolidone TFP = 2,2,3,3-tetrafluoropropanol CYC = cyclohexanol 2P = 2-pyrrolidone P12 = propane- 1,2-diol UR = Urea CET= cetyl ammonium bromide PHO = Na2HPO, and TBT = tertiary butanol TDG = thiodiglycol GLY = glycerol P-1,5 = Pentane-1,5-diol PEG 200 = Polyethylene glycol (average molecular weight of 200) H - 1,6 = Hexane 1,6-diol CAP = caprolactone 16 CAP-L = caprolactam TEA = triethanolamine DEG-MBE = diethylene glycol monobutyl ether EG = ethylene glycol BUT = y-butyrolactone TABLE 3
Ink Dye Dye Water PG DEG NMP P-1,5 TEA CYC BUT CAP EG CAP-L Content 1 1 3.0 90 5 4.8 0.2 2 2 10.0 85 3 3 3 5 3 2 2.1 91 8 1 1 4 1 3.1 86 5 0.2 4 4.8 2 1.1 81 9 0.5 0.5 6 1 2.5 60 4 15 3 3 6 9 4 7 1 5 65 20 5 10 5 8 1 2.4 75 5 4 5 6 5 9 2 4.1 80 3 5 2 9.7 0.3 1 3.2 65 5 4 6 5 4 5 11 2 5.1 96 4 6 12 2 10.8 90 5 5 13 1 10.0 80 2 6 2 5 1 14 2 1.8 80 5 4 1 2.6 84 11 15 16 1 3.3 80 2 10 2 5 6 17 2 12.0 90 7 0.3 2.7 18 2 5.4 69 2 20 2 1 3 3 TABLE 4 -,/:
Ink Dye Dye Water GLY DEG NMP CET TBT TDG UR PHO 2P P12 Content 19 1 3.0 80 15 0.2 4.8 2 9.0 90 5 1.2 5 21 1 1.5 85 3.8 5 0.16 4.64 0.2 22 1 2.5 90 6 3.88 0.12 23 2 3.1 82 4 8 0.3 5.7 24 2 0.9 85 10 4.8 0.2 1 8.0 90 4.7 5 0.3 26 1 4.0 70 10 4 1 4 11 27 1 2.2 75 4 10 3 2 6 28 2 10.0 91 6 3 29 2 9.0 76 9 7 2.05 0.95 5 1 5.0 78 5 11 6 31 1 5.4 86 7 7 32 2 2.1 70 5 5 5 0.1 0.2 0.1 5 0.1 9.5 33 1 2.0 90 10 34 1 2 88 2 10 2 5 78 5 12 5 36 2 8 70 2 8 15 5 37 2 10 80 8 12 38 1 10 80 10 co TABLE5
Ink Dye Dye Water PEG DEG- NMP H-1,6 TEA TF BUT CAP EG CAP-L Content 200 MBE 39 1 2.0 80 5 6 4 5 2 3.0 90 5 4.8 0.2 41 2 10.0 85 3 3 3 5 1 42 1 2.1 91 8 1 43 1 3.1 86 5 0.2 3.8 5 44 1 1.1 81 9 0.5 0.5 9 2 2.5 60 4 15 3 3 6 5 4 46 2 5 65 20 10 47 2 2.4 75 5 4 5 6 5 48 1 4.1 80 3 5 2 9.7 0.3 49 1 3.2 70 5 4 6 5 4 6 5 2 5.1 96 4 51 1 10.8 90 5 5 52 2 10.0 80 2 6 2 5 1 4 53 2 1.8 80 5 15 54 1 2.6 84 11 5 2 3.3 80 2 10 2 6 56 1 12.0 90 7 0.3 2.8 57 1 5.4 69 2 20 2 1 3 3 58 2 6.0 91 4 5 (0 TABLE 6
Ink Dye Dye Water PEG DEG- NMP H-1,6 TEA TFP BUT CAP EG CAP-L Content 200 MBE 59 1 2.0 80 5 6 4 5 2 3.0 90 5 4.8 0.2 61 2 10.0 85 3 3 3 5 1 62 1 2.1 91 8 1 63 1 3.1 86 5 0.2 3.8 5 64 1 1.1 81 9 0.5 0.5 9 2 2.5 60 4 15 3 3 6 5 4 66 2 5 65 20 10 67 2 2.4 75 5 4 5 6 5 68 1 4.1 80 3 5 2 9.7 0.3 69 1 3.2 70 5 4 6 5 4 6 5 2 5.1 96 4 71 1 10.8 90 5 5 72 2 10.0 80 2 6 2 5 1 4 73 2 1.8 80 5 15 74 1 2.6 84 11 5 2 3.3 80 2 10 2 6 76 1 12.0 90 7 0.3 2.8 77 1 5.4 69 2 20 2 1 3 3 78 2 6.0 91 4 5 - 3 1 21

Claims (16)

  1. A compound of Formula (1) and salts thereof: 0 1 R\ k Ar-N OH N L 11 N HS'- H 03' 4 S03 Formula (1) wherein:
    Arl is substituted aryl carrying at least one -COOH group; R' is H or optionally substituted alkyl; L is substituted phenyl carrying at least one substituent at the 2- position, or optionally substituted naphthyl.
  2. 2.A compound according to claim 1 wherein Arl is a group of the Formula (2):
    (HOOC),,, 9_ (B)P Formula (2) wherein:
    each B independently is a substituent other than H; p is 0 to 4; n is 1 or 2; and (n+p) is 5 or less.
  3. 3. A compound according to either claim 1 or claim 2 wherein L is of the Formula (3) or (4):
    X G- (T), M Formula (3) Formula (4) wherein:
    X and each T independently is a substituent other than H; m is 0 to 4; and 22 q is 0 to 7.
  4. 4. A compound according to claim 1 of the Formula (5) and salts thereof:
    0 Xl 4 1-:
    R\ 'I OH N HOOC H 31P S03H Formula (5) wherein:
    xl 'S -S03H, -CF3, -NH2, halo, Cl-6-alkoxy or C,,-alkyl optionally substituted by -OH, -COOH, -NH2 or -SOR and R 4 is H or Cl,-alkyl optionally substituted by -OH, -COOH or -S03H.
  5. 5. A compound according to claim 4 wherein the -COOH group is attached ortho to the azo group; R 4 is H or Cl,-alkyl; and X' is -Cl, C,-alkyl or-S03H.
    is
  6. 6. A composition comprising:
    (a) one or more compound according to any one of claims 1 to 5; and (b) one or more water-soluble magenta dye other than a compound according to any one of claims 1 to 5.
  7. 7. A composition according to claim 6 comprising:
    (a) from 1 to 99 parts in total of the compound(s) according to any one of claims 1 to 5; and (b) from 99 to 1 parts in total of the water-soluble magenta dye(s); wherein the parts are by weight and the sum of the parts (a) and (b) = 100.
  8. 8. A liquid composition comprising: (a) a compound according to any one of claims 1 to 5, or a composition according to either claim 6 or claim 7; and (b) a liquid medium.
  9. 9. A liquid composition according to claim 8 wherein the liquid medium comprises (i), (ii) or (iii):
    W a mixture of water and an organic solvent; (ii) an organic solvent free from water; or 23 (iii) a low melting point solid.
  10. 10. A liquid composition according to either claim 8 or claim 9 which is an ink.
  11. 11. A process for printing an image on a substrate comprising applying thereto by means of an ink jet printer an ink containing a compound according to any one of claims 1 to 5, or a composition according to either claim 6 or claim 7.
  12. 12. A substrate printed with a liquid composition according to either claim 8 or claim 9, or by means of the process according to claim 11.
  13. 13. An ink jet printer cartridge comprising a chamber and ink, wherein the ink is present in the chamber and the ink contains a compound according to any one of claims I to 5, or a composition according to either claim 6 or claim 7.
    is
  14. 14. An ink jet printer containing an ink jet printer cartridge, wherein the ink jet printer cartridge is as defined in claim 13.
  15. 15. A compound substantially as hereinbefore defined with reference to any one of the examples.
  16. 16. An ink substantially as hereinbefore defined with reference to any one of the examples.
GB9919873A 1998-08-28 1999-08-24 8-Aroylamino-2-[(carboxyaryl)azo]-1-hydroxy-naphthalene-disulphonic acid dyes for use in ink jet inks Expired - Fee Related GB2340839B (en)

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JP6031044B2 (en) 2011-01-14 2016-11-24 大連理工大学Ｄａｌｉａｎ Ｕｎｉｖｅｒｓｉｔｙ ｏｆ Ｔｅｃｈｎｏｌｏｇｙ Anthrapyridone sulfonic acid compound and its preparation
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