Combinations of oxonols and a polymer having infrared-absorbing groups are known from WO 2001/94123.

JP-A-2001-342364 discloses, in general, the use of oxonols in printing colorants and also in further applications without mention of highly soluble compounds.

Compositions comprising at least one oxonol dye and at least one metal complex are known from WO 03/042989.

The object of the present invention is to provide compounds having high tinctorial strength that are very readily soluble in organic solvents and only sparingly soluble in water and that can be used, for example, as soluble printing dyes and wood stains, and in the colouring of polar plastics. This cannot be achieved using the compounds known today.

It has now been found, surprisingly, that the dyes according to the invention, which are in the form of specific organic salts and contain one or more branched aliphatic substituents, achieve the above-mentioned object to a substantial degree.

The present invention accordingly relates to dyes of formula wherein

R and R, are each independently of the other C,-C12alkyl which may, from C3 on, be branched, C,-C, 2alkoxy the alkyl radical of which may, from C3 on, be linear or branched, unsubstituted or C,-C, 2alkyl-or C1-C, 2alkoxy-substituted aryl, especially phenyl, or C,-C, 2- alkoxy-substituted C,-C, 2alkyl and Cat+ is an organic cation.

Dyes of formula (1) wherein R and R, are each independently of the other C1-C12alkyl which may, from C3 on, be branched, C,-C, 2alkoxy the alkyl radical of which may, from C3 on, be linear or branched, or C1-C12alkyl- or C1-C12alkoxy-substituted aryl are important.

Among the dyes of formula (I), preference is given to those wherein R is branched C3-C12- alkyl or C3-C12alkoxy, the alkyl radical in C3-Cl2alkoxy being branched, or is C1-C12alkoxy- substituted C1-C12alkyl and R, is C,-C, 2alkyl, branched C3-C12alkyl or C3-C, 2alkoxy, the alkyl radical in C3-C, 2alkoxy being branched, or is C,-C, 2alkoxy-substituted C,-C, 2alkyl.

Preference is likewise given to dyes of formula (1) wherein Cat+ is an organic cation containing at least one branched radical.

In the context of the present invention, an organic cation Cat+ containing at least one branched radical is understood to mean, for example, a primary amine having a branched C3-C14alkyl chain or a secondary, tertiary or quaternary amine having at least linear or branched C3-C, 4alkyl chain.

R is preferably isopropoxypropyl (C3H6-O-CH (CH3) 2).

R, is preferably ethyl, butyl or isopropoxypropyl.

R2 R2 Cat+ is preferably the ammonium cation H-+ R3 of an amine of formula N-R3, R4 R4 wherein R2 and R3 are each independently of the other hydrogen, C2-C14alkyl unsubstituted or hydroxy-or amino-substituted and optionally interrupted by an oxygen atom and R4 is

C2-C14alkyl unsubstituted or hydroxy-or amino-substituted and optionally interrupted by an oxygen atom.

Cat+ is more especially a cation derived from Primene 81 R3, a commercial product from Rohm & Haas, a primary amine mixture with heavily branched C, 2-C, aalkyl side chains, or is derived from C,-C, 4tetraalkylammonium hydroxide.

The cations Cat+ may also be in the form of mixtures.

The dyes of formula (1) can be prepared according to processes known perse, for example by reacting 1 mol of a compound of formula and 1 mol of a compound of formula with 1 mol of the compound of formula in an organic solvent and in the presence of a base to form a compound of formula

R, R, and Cat+ having the definitions and preferred meanings given above.

It is also possible to use mixtures of pyridones; equally, other propionic dialdehyde derivatives can be used, such as Dianil or Dianil hydrochloride.

In the case of a primary, secondary or tertiary amine, Cat+ is derived from the amine itself and, in the case of tetraalkylammonium, is derived from the corresponding hydroxide.

Solvents may in this case be water or organic polar solvents, for example alcohols, amides, ketones or also amines. Where amines are used as solvents (e. g. pyridine, triethylamine), the corresponding pyridinium or triethylammonium salt is obtained, which can then be converted into the soluble product by treatment with the corresponding desired cation.

Equally, it is possible using an inorganic base to prepare the corresponding oxonol salt, which likewise yields the highly soluble dye. The reaction temperature may generally be from room temperature (approximately 20°C) to the boiling point of the solvent used.

I The compounds of formula (2) to (4) are known or can be prepared in a manner known per se.

The organic solvents in which the dyes according to the invention are soluble are, for example, linear, branched or cyclic alcohols, linear, branched or cyclic ketones, carboxylic acid esters, toluene and xylene.

The dyes according to the invention are especially very readily soluble in polar solvents, especially in methanol, ethanol, ethyl acetate, butyl acetate and isobutyl methyl ketone.

The present invention relates also to a process for the production of coloured plastics or polymeric colour particles, which comprises blending with one another a high molecular weight organic material and a tinctorially effective amount of at least one dye of formula (1).

The colouring of high molecular weight, organic substances using the dye of formula (1) is effected, for example, by admixing such a dye with such substrates using roll mills or mixing or grinding apparatuses, with the result that the dye is dissolved or finely distributed in the high molecular weight material. The high molecular weight organic material with the admixed dye is then processed according to methods known per se, such as, for example, calendering, compression moulding, extrusion, coating, spinning, pouring or injection moulding, whereby the coloured material acquires its final shape. Admixture of the dye can also be effected immediately prior to the actual processing step, for example by continuously simultaneously feeding pulverulent dye and a granulated or pulverulent high molecular weight organic material and, optionally, also additional ingredients, such as additives, directly into the intake zone of an extruder, the constituents being mixed just prior to processing.

Generally, however, preference is given to mixing the dye into the high molecular weight organic material beforehand, because more evenly coloured substrates can be obtained.

It is often desirable, in order to produce non-rigid moulding or to reduce their brittleness, to incorporate so-called plasticisers into the high molecular weight compounds prior to shaping.

There may be used as plasticisers, for example, esters of phosphoric acid, phthalic acid or sebacic acid. In the process according to the invention, the plasticisers may be incorporated into the polymers before or after the incorporation of the colorant. It is also possible, in order to achieve different shades of colour, to add to the high molecular weight organic materials, in addition to the dye of formula (1), also further dyes or other colorants in any desired amounts, optionally together with further additives, e. g. fillers or siccatives.

Preference is given to the colouring of thermoplastic plastics, especially in the form of fibres or films.

Preferred high molecular weight organic materials that can be coloured in accordance with the invention are, very generally, polymers having a dielectric constant 2 2.5, especially polyesters, polycarbonate (PC), polystyrene (PS), polymethyl methacrylate (PMMA), polyamide, polyethylene, polypropylene, styrene/acrylonitrile (SAN) and acrylonitrile/butadiene/styrene (ABS). Especially preferred are polyesters and polyamide.

More especially preferred are linear aromatic polyesters obtainable by polycondensation of terephthalic acid and glycols, especially ethylene glycol, or condensation products of terephthalic acid and 1,4-bis (hydroxymethyl) cyclohexane, for example polyethylene

terephthalate (PET) or polybutylene terephthalate (PBTP); also polycarbonates, e. g. those obtained from a, a-dimethyl-4, 4-dihydroxy-diphenylmethane and phosgene, or polymers based on polyvinyl chloride and on polyamide, e. g. polyamide-6 or polyamide-6. 6.

The dyes according to the invention impart to the above-mentioned materials, especially the polyester and polyamide materials, shades of strong colour having very good in-use fastness properties, especially a good fastness to light.

The dyes of formula (1) according to the invention can also be used in the printing of semi- synthetic and, especially, synthetic hydrophobic fibre materials, more especially textile materials, and also in the printing of paper, plastics films or metal foils, especially aluminium foils.

Semi-synthetic textile materials that come into consideration are especially cellulose 2/2 acetate and cellulose triacetate.

Synthetic hydrophobic textile materials consist especially of linear, aromatic polyesters, for example polyesters of terephthalic acid and glycols, especially ethylene glycol, or condensation products of terephthalic acid and 1,4-bis (hydroxymethyl) cyclohexane ; of polycarbonates, e. g. polycarbonates obtained from a, a-dimethyl-4, 4'-dihydroxy-diphenyl- methane and phosgene, and of fibres based on polyvinyl chloride and on polyamide.

The dyes according to the invention are also highly suitable for the printing of polyester/wool and polyester/cellulosic fibre blends.

The said textile material can be in a variety of processing forms, e. g. in the form of fibres, yarns or non-wovens, in the form of woven fabrics or knitted fabrics.

It is advantageous to convert the dyes according to the invention into a dye preparation prior to use. For that purpose, the dye is so ground that its particle size is on average from 0.1 to 10 microns. Grinding can be carried out in the presence of dispersants. For example, the dried dye is ground with a dispersant or is kneaded into paste form with a dispersant and then dried in vacuo or by atomisation. The preparations so obtained can be used, after the addition of water, to prepare printing colorants or printing pastes.

The present invention relates also to the use of the dyes according to the invention in the preparation of printing colorants or printing pastes, optionally also together with other dyes, as well as to the printing colorants or printing pastes obtained.

The amount of dyes to be added to the printing colorants or printing pastes is dependent on the desired colour strength; in general, amounts of from 0.01 to 15% by weight, especially from 0.02 to 10% by weight, based on the material to be printed, have proved suitable.

For printing, the customary thickeners will be used, e. g. modified or unmodified natural products, for example alginates, British gum, gum arabic, crystal gum, carob flour, tragacanth, carboxymethyl cellulose, hydroxyethyl cellulose, starch or synthetic products, for example polyacrylamides, polyacrylic acid or copolymers thereof, or polyvinyl alcohols.

The printing pastes also comprise, if desired, acid donors, such as butyrolactone or sodium hydrogen phosphate, preservatives, sequestering agents, emulsifiers, organic solvents, e. g. alcohols, esters, toluene and xylene, binders, e. g. nitrocellulose and vinyl copolymers, softeners, e. g. citric acid, oxidising agents, deaerating agents, light stabilisers and UV stabilisers.

For printing, the printing paste is applied directly to the entire surface of the material to be printed or to parts thereof, printing machines of the customary type, e. g. flexographic/intaglio printing, offset printing, rotary or flat-film printing machines, advantageously being used. The printing pastes according to the invention are also suitable for transfer printing.

The dyes according to the invention impart to the mentioned materials, especially to polyester materials, level colour shades having very good in-use fastness properties.

The present invention relates also to the use of the dyes of formula (1) in the preparation of printing inks, preferably for inks used in an ink-jet method.

The present invention relates also to the aqueous inks used in the ink-jet printing method that comprise at least one dye of formula (1).

The total amount of dyes present in the inks is preferably from 0.5 to 35% by weight, especially from 1 to 30% by weight and more especially from 1 to 20% by weight, based on the total weight of the ink. The especially preferred lower limit is 1.2% by weight, especially 1.5% by weight. The especially preferred upper limit is 15% by weight, especially 10% by weight.

The inks preferably comprise a solubiliser or a humectant, such as a water-miscible organic solvent, for example a C :-C4alcohol, such as methanol, ethanol, n-propanol, isopropanol, n-butanol, sec-butanol, tert-butanol or isobutanol ; an amide, e. g. dimethylformamide or di- methyl acetamide; a ketone or ketone alcohol, e. g. acetone, methyl isobutyl ketone, diace- tone alcohol ; an ether, e. g. tetrahydrofuran or dioxan ; a nitrogen-containing heterocyclic compound, e. g. N-methyl-2-pyrrolidone or 1, 3-dimethyl-2-imidazolidone ; a polyalkylene glycol, preferably a low molecular weight polyethylene glycol having a molecular weight of from 100 to 800, e. g. diethylene glycol, triethylene glycol, tetraethylene glycol, polyethylene glycol 200, polyethylene glycol 300, polyethylene glycol 400 or polyethylene glycol 600, especially having a molecular weight of from 150 to 400, or a low molecular weight poly- propylene glycol, e. g. dipropylene glycol, tripropylene glycol, polypropylene glycol P 400 or polypropylene glycol P 425; a C,-C4alkyl ether of a polyalkylene glycol, e. g. diethylene glycol monobutyl ether, 2- (2-methoxyethoxy) ethanol, 2- (2-ethoxyethoxy) ethanol, 2- [2- (2-methoxy- ethoxy) ethoxy] ethanol or 2- [2- (2-ethoxyethoxy) ethoxy] ethanol ; a C2-C6alkylene glycol or a thioglycol, e. g. ethylene glycol, propylene glycol, butylen glycol, 1, 5-pentanediol, thiodi- glycol, hexylene glycol ; further a polyol, e. g. glycerol or 1,2, 6-hexanetriol ; or a C,-C4alkyl ether of a polyhydric alcohol, e. g. 2-methoxyethanol or 1-methoxypropan-2-ol.

More especially, the inks comprise at least one solubiliser or humectant from the group consisting of polyethylene glycols having a molecular weight of from 150 bis 400, diethylene glycol monobutyl ether, N-methyl-2-pyrrolidone and glycerol and especially tetraethylene glycol, polyethylene glycol 400, diethylene glycol monobutyl ether and glycerol, usually in an amount of from 2 to 30% by weight, especially from 5 to 25% by weight and more especially from 20 to 25% by weight, based on the total weight of the ink.

The inks may in addition comprise solubilisers, e. g. c-caprolactam.

As humectants in the inks according to the invention there also come into consideration, for example, urea or a mixture of sodium lactate (advantageously in the form of a 50 to 60% aqueous solution) and glycerol and/or propylene glycol in amounts of preferably from 0.1 to 30% by weight, especially from 2 to 30% by weight.

The inks may comprise thickeners of natural or synthetic origin, inter alia for adjusting the viscosity.

Examples of thickeners that may be mentioned include commercially available alginate thickeners, starch ethers and carob flour ethers, especially sodium alginate on its own or in admixture with modified cellulose, for example methyl, ethyl, carboxymethyl, hydroxyethyl, methylhydroxyethyl, hydroxypropyl or hydroxypropylmethyl cellulose, especially with preferably from 20 to 25 percent by weight of carboxymethyl cellulose. There may furthermore be mentioned as synthetic thickeners, for example, those based on poly (methy acrylic acids or poly (meth) acrylamides.

The inks contain such thickeners in an amount of, for example, from 0.01 to 2% by weight, especially from 0.01 to 1 % by weight and more especially from 0.01 to 0.5% by weight, based on the total weight of the ink.

The inks may also comprise buffer substances, for example borax, borate, phosphate, poly- phosphate or citrate. Examples that may be mentioned are borax, sodium borate, sodium tetraborate, sodium dihydrogen phosphate, disodium hydrogen phosphate, sodium triply- phosphate, sodium pentapolyphosphate and also sodium citrate. They are used especially in amounts of from 0.1 to 3% by weight, more especially from 0.1 to 1 % by weight, based on the total weight of the ink, to establish a pH value of, for example, from 4 to 9, especially from 5 to 8.5.

Further additives that may be present in the inks are surfactants or wetting agents.

Surfactants or wetting agents that come into consideration are the commercially available anionic or non-ionic surfactants.

Furthermore, the inks may in addition comprise customary additives, e. g. anti-foams or especially substances that inhibit fungal and/or bacterial growth. Such additives are usually used in amounts of from 0.01 to 1 % by weight, based on the total weight of the ink.

Suitable preservatives include formaldehyde-yielding agents, e. g. paraformaldehyde and trioxane, especially aqueous formaldehyde solutions, for example 30 to 40 percent by weight formaldehyde solutions, imidazole compounds, e. g. 2- (4-thiazolyl) benzimidazole, thiazole compounds, e. g. 1, 2-benzisothiazolin-3-one or 2-n-octyl-isothiazolin-3-one, iodine compounds, nitriles, phenols, haloalkylthio compounds or pyridine derivatives, especially 1, 2- benzisothiazolin-3-one or 2-n-octyl-isothiazolin-3-one.

The inks can be prepared in customary manner by mixing together the individual components, for example in the desired amount of ethanol or water. Suspended matter and insoluble components present in the inks are removed, for example, by filtration through filters having a pore size of from 0.2 to 0.5 m.

Preference is given to inks having a viscosity of from 1 to 40 mPa s, especially from 1 to 20 mPa s and more especially from 1 to 10 mPa s.

The inks according to the invention are suitable for use in recording systems in which the ink is expressed from a small aperture in the form of droplets and directed onto a planar substrate on which an image is formed. Suitable substrates include, for example, paper, plastics films or textile fibre materials, preferably paper or plastics films and especially a plastics-coated paper. Suitable recording systems include, for example, commercially available ink-jet printers for use in paper printing or textile printing.

As examples of paper that can be printed with the inks according to the invention there may be mentioned commercially available ink-jet paper, photo paper, glossy paper, plastics- coated paper, e. g. Epson Ink-jet Paper, Epson Photo Paper, Epson Glossy Paper, Epson Glossy Film, HP Special Ink-jet Paper, Encad Photo Gloss Paper and Ilford Photo Paper.

Plastics films that can be printed with the inks according to the invention are, for example, transparent or cloudy/opaque. Suitable plastics films are, for example, 3M Transparency Film. Preference is given to glossy paper, such as, for example, Epson Glossy Paper.

As textile fibre materials there come into consideration especially nitrogen-containing or hydroxy group-containing fibre materials, for example woven textile fabric made of cellulose, silk, wool or synthetic polyamides, especially silk.

In the case of the ink-jet printing method, individual droplets of ink are sprayed onto a substrate from a nozzle in a controlled manner. It is mainly the continuous ink-jet method and the drop-on-demand method that are used for that purpose. In the case of the continuous ink-jet method, the droplets are produced continuously, droplets not required for the printing operation being discharged into a receptacle and recycled. In the case of the drop-on- demand method, on the other hand, droplets are generated as desired and used for printing; that is to say, droplets are generated only when required for the printing operation. The production of the droplets can be effected, for example, by means of a piezo ink-jet head or by thermal energy (bubble jet). For the process according to the invention, printing by means of a piezo ink-jet head is preferred, but preference is given also to printing according to the continuous ink-jet method.

The present invention relates also to the above-mentioned uses of the dyes according to the invention, such as in a method of printing semi-synthetic or synthetic hydrophobic fibre material, especially textile material, which comprises applying the dyes according to the invention to the said material. The mentioned hydrophobic fibre material is preferably textile polyester material.

Further substrates that can be treated by the process according to the invention and also preferred process conditions can be found hereinabove in the more detailed explanation of the use of the dyes according to the invention.

The invention relates also to the hydrophobic fibre material, preferably polyester textile material, paper and plastics films or metal foils, printed using the said process.

The dyes of formula (1) according to the invention are furthermore suitable for other recording methods, for example thermotransfer printing.

The following Examples serve to illustrate the invention. Unless otherwise indicated, parts are parts by weight and percentages are percentages by weight. The temperatures are given

in degrees Celsius. The relationship between parts by weight and parts by volume is the same as that between grams and cubic centimetres.

Example 1: 75.09 g (0.3 mol) of N- (3-isopropoxy-propyl)-3-cyano-4-methyl-2-pyridone are introduced, under nitrogen, into 300 ml of ethanol and then 27.24 g (0.147 mol) of Primene 81 Re (Rohm & Haas) and 24.63 g (0.15 mol) of tetramethoxypropane (Degussa) are added. The suspension is refluxed for 21 hours, and then the resulting blue solution is fully concentrated. The last residues of solvent can be distilled off under a high vacuum. 61 g (98% of theory) of a pulverulent blue compound of the formula below having a very high level of solubility in ethanol, methyl ethyl ketone and ethyl acetate are obtained, 4laX (DMF): 603 nm, CH3 CH3 NC, CH-CH = CH CN + NC CH-CH = CH CN + Primene 81 R O N O N O CH2 CH2-CH2-CH2-O-CH (CH3) 2 CH2 I o-CH (CH3) 2 Example 2: 115.7 g (0.3 mol) of wet (65%) N- (3-isopropoxy-propyl)-3-cyano-4-methyl-2-pyridone are introduced, under nitrogen, into 150 ml of pyridine, and then 24.63 g (0.15 mol) of tetra- methoxypropane (Degussa) are added. The suspension is refluxed for 22 hours and then cooled to room temperature. Stirring is continued for a further 24 hours at room temperature, and then the precipitate is filtered off with suction and washed with a small amount of ethanol. The blue product (pyridinium salt) is dried overnight at 65°C under 100 mbar.

A compound of formula (6)

is obtained.

22.5 g of the above-prepared product is stirred thoroughly at room temperature together with 6.77 g (36.9 mmol) of Primene 81 Ra (Rohm & Haas) in 300 ml of acetone, the product dissolving completely. The solution is concentrated and the product obtained is dried at room temperature under a high vacuum. Yield : 99.8% of theory. AmaX (DMF): 603 nm.

The following compounds listed in Table 1 were prepared analogously to Example 1: Table 1 CH3 CH3 NC CH-CH = CH CN at+ ll Cat O N''O O NI'O i R R R R, Cat' (DMF) C3H6-O-CH (CH3) 2 C3H6-O-CH (CH3) 2 Bu4N+ 603 C3H6-O-CH (CH3) 2 C3H6-O-CH (CH3) 2 Oct4N+ 603 C3He-O-CH (CH3) 2 C3H6-O-CH (CH3) 2 HexNH3+ 603 C3H6-O-CH (CH3) 2 C3H6-O-CH (CH3) 2 Pe4N+ 603 C3H6-O-CH (CH3) 2 C3H6-O-CH (CH3) 2 Oct3NH+ 603 C3H6-O-CH (CH3) 2 ethyl Primene 81 R+ 603 C3H6-O-CH (CH3) 2 ethyl Pe4N+ 603 ethyl ethyl Primene 81 R+ 603 ethyl ethyl Bu4N+ 603 ethyl ethyl Pe4N+ 602 In Table 1, Bu denotes n-butyl, Pe denotes n-pentyl, Hex denotes n-hexyl and Oct denotes n-octyl Example 3: 27.29 g (0.1 mol) of N- (3-isopropoxy-propyl)-3-cyano-4-methyl-2-pyridone (91.7%) and 19.43 g (0.1 mol) of N-ethyl-3-cyano-4-methyl-2-pyridone (92%) are introduced into 150 ml of (technical grade) isobutyl methyl ketone under nitrogen, and then 9.91 g of potassium acetate (99%) followed by 16.67 g (0.1 mol) of tetramethoxypropane (98.6%) are added. The suspension is heated for 3 hours, with stirring, at 104-106°C, the methanol formed being distilled off. The suspension is then cooled to 5°C and filtered and the precipitated product is subsequently washed twice with 50 ml of isobutyl methyl ketone each time. The blue product (mixture of the potassium salts of the symmetrically and asymmetrically substituted compounds) is dried overnight at 65°C under 100 mbar to yield a compound of formula (7) ; yield : 48.0 g = 95.5% of theory, X. x (DMF): 603 nm.

(7).

Example 4: 48 g (0.0955 mol) of the compound of formula (7) prepared in Example 3 are introduced into 350 ml of deionised water and then heated to 50°C. Subsequently, while stirring vigorously, 350 ml of isobutyl methyl ketone and then 32.39 g (0.0955 mol) of tetrabutylammonium bromide are added thereto. After 5 min. , the phases are separated and the aqueous phase is again extracted by shaking with isobutyl methyl ketone. The combined organic phases are concentrated and the resulting product is dried at room temperature under a high vacuum to yield a compound of formula (8) ; yield : 67.09 g = 99.5% of theory, (DMF): 603 nm.

The following compounds and mixtures listed in Table 2 are obtained analogously to Example 3 or 4: Table 2 CH3 CH3 NC, CH-CH = CH ßCN Cat+ R R1 R R, Cat' (DMF) phenyl phenyl Primene 81 R+ 605 phenyl C3H6-O-CH (CH3) 2 Primene 81 R+ 604 phenyl C3H6-O-CH (CH3) 2 pyridinium+ 605 phenyl ethyl Primene 81 R+ 603 methyl ethyl Primene 81 R+ 602 C3H6-O-CH (CH3) 2 C3H6-O-CH (CH3) 2 Pr4N+ 602 ethyl ethyl Pe4N+ 602 ethyl C3HB-O-CH (CH3) 2 Pe4N+ 602 ethyl C3H6-O-CH (CH3) 2 Bu4N+ 602 In Table 2, Pr denotes propyl, Bu denotes n-butyl and Pe denotes n-pentyl, Example 1 of a printing colorant : 2.0% by weight of the dye of formula

are stirred into 98.0% by weight of a formulation consisting of 12.0% by weight of NC AH 27 (20% ATBC) [a nitrocellulose, soluble in ethanol, containing 20% by weight of acetyl tributyl citrate] 2.0% by weight of Hercolyn DE [a water-repellent agent] 10.0% by weight of ethoxypropanol 20.0% by weight of ethyl acetate and 56.0% by weight of ethanol until homogeneous.

5 10 15 20 25 The printing colorant gives a brilliant intense blue coloration on paper, plastics films or metal foils.

Example 2 of a printing colorant : 2.0% by weight of the dye of formula CH3 CH3 0 NC CH-CH = CH-CN + I Pdmene 81 R (10) O N''O NI'O i i C3Hs-O-CH (CH3) 2 CH2CH3 are stirred into 98.0% by weight of a formulation consisting of 14.0% by weight of vinylite VYHH (UCC) [a vinyl chloride/vinyl acetate copolymer (85%/15%)] 10.0% by weight of ethoxypropanol and 76.0% by weight of MEK [methyl ethyl ketone] until homogeneous.

The printing colorant gives a brilliant intense blue coloration on paper, plastics films or metal foils.

Example 3 of a printing colorant : 2.0% by weight of the dye of formula are stirred into 98.0% by weight of a formulation consisting of 12.0% by weight of NC AH 27 (20% ATBC) [a nitrocellulose, soluble in ethanol, containing 20% by weight of acetyl tributyl citrate] 2.0% by weight of Hercolyn DE [a water-repellent agent] 10.0% by weight of ethoxypropanol 20.0% by weight of ethyl acetate and 56.0% by weight of ethanol

until homogeneous.

The printing colorant gives a brilliant intense blue coloration on paper, plastics films or metal foils.