MXPA97003118A

MXPA97003118A - Metine and azametine dyes based on trifluorometilpiride

Info

Publication number: MXPA97003118A
Application number: MXPA/A/1997/003118A
Authority: MX
Inventors: Johann Schmidt Andreas; Sens Rudiger; Etzbach Karlheinz
Original assignee: Basf Aktiengesellschaft
Priority date: 1994-11-10
Filing date: 1997-04-29
Publication date: 1997-06-01

Abstract

Pyridone dyes of the formula (I), wherein X is nitrogen or CH, R1 is a carbocyclic or heterocyclic 5-membered or 6-membered radical, R2 is cyano, carbamoyl, C1-C6 alkoxycarbonyl or C1-C4 alkanoyl and R3 is C 1 -C 13 substituted or unsubstituted alkyl, substituted or unsubstituted phenyl, or substituted or unsubstituted amino, a method for its thermal transfer and a method for coloring or printing materials by means of novel dyes

Description

META INA V AZAMETI COLORANTS BASED ON TR IFLUOROMETILPYRIDONES The present invention relates to novel pyridone dyes of the formula I R3 wherein X is nitrogen or CH, R1 is a carbocyclic or heterocyclic radical of 5 members or 6 members, R2 is cyano, carbamoyla, alkoxycarbani C1-C6 or C1-C4 alkanoyl and R3 is C1-C13 alkyl, substituted or unsubstituted, and may be interrupted by 1 to 3 oxygen ether atoms, is either substituted or unsubstituted phenyl or a radical of the formula NE1E3, where El and E2 are identical or different and, independently of each other, are each hydrogen, substituted or unsubstituted C1-C13 alkyl and may be interrupted by I3 oxygen ether atoms, or are each C5-C7 cycloalkyl, substituted or unsubstituted phenyl, substituted or unsubstituted pyridyl, C1-6 alkanoyl C13 substituted or unsubstituted, C 1 -C 13 alkoxycarbonyl, aikhi lsu Ifoni lo substituted or unsubstituted C 1 -C 13, C 1 -C 7 cycloalkylsulfonyl, substituted or unsubstituted phenylsul fonyl, substituted or unsubstituted pyridylsulfonyl, substituted or unsubstituted benzoyl, pi i-1 Icarb oni lo o tieni lcarbani lo or else El and E2, together with the nitrogen atom that links them, are succinimido unsubstituted or substituted by C1-C4 alkyl, phthalimido unsubstituted or substituted by C1-C4 alkyl or a radical saturated heterocyclic of 5 members or of > members that may contain additional heteroatoms, a process for their thermal transfer and a process for coloring or printing synthetic materials by means of novel dyes. JP-A-339 237/1993 discloses the preparation of 1-l-l-3-cyano-4-trof luoro and i-l-6-hydroxypyrid-2-one. In addition, JP-A-331 382/1993 and Bull. Chem. Soc. Japan 6é < 1993), 1790-1794, present azo dyes having the aforementioned compound as a coupling component. It is an object of the present invention to provide novel dyestuffs and azame dyes which have profitable performance characteristics. We have found that this object is achieved by means of the pyridone dyes of the formula I which are defined at the outset. R 1 is a carbocyclic or heterocyclic radical, preferably aromatic, 5-membered or 6-membered, substituted or unsubstituted and which may be benzofused.

R1 can be derived, for example, from components of the benzene, indole, quinaline, naphthalene, pyrrole, thiazole, benzyl idazole, benzothiazole, thiophene, or pyridine series. Important Rl radicals are, for example, the radicals of formulas Ia to II.

(Ha) (Hb) (lie) (lid) (lie) (iif) (iig) (Hh) ("i) (" i) where n is 0 or 1, Zl is hydrogen, C1-C13 alkyl which may be interrupted by 1 to 3 oxygen ether atoms, or is hydroxyl, C1-C4 alkoxy, alkyl lsul foni lamino C1-C4, mono- or dialki laminosul foni lamino C1-C4 or a radical -NHC0Z7 or - HC02Z7, where Z7 is phenyl, benzyl, tolyl or C1-C13 alkyl which may be interrupted by 1 to 3 oxygen ether atoms, Z2 is hydrogen, C1-C4 alkyl or C1-C4 alkoxy, Z3 and Z4 are identical or different and, independently of each other, are each hydrogen or substituted or unsubstituted C1-C13 alkyl and can are interrupted by 1 to 3 oxygen ether atoms or are each C3-C4 alkenyl, C5-C7 cycloalkyl, phenyl or tolyl or, together with the nitrogen atom linking them, are a saturated 5-membered heterocyclic radical or of > members which may contain additional heteroatoms, Z5 is hydrogen or C1-C4 alkyl and ZA is hydrogen, halogen, C1-C13 alkyl, substituted or unsubstituted phenyl, substituted or unsubstituted benzyl, C5-C7 cycloalkyls, thienyl, hydroxyl, alkoxy C1-C4, C1-C4 alkylthi, or mono-C1-C1-C13. All alkyl or alkenyl groups found in the aforementioned formulas can be straight chain or branched. When urging substituted alkyl radicals in the aforementioned formulasUnless otherwise stated, suitable substitutents may be, for example, cyclohexyl, substituted or unsubstituted phenyl, C1-C8 alkanoyloxy, C1-C8 alkylaminocarboni loxy, C1-C8 alkoxycarbonyl, C1-C8 alkoxycarbonyl loxy, the alkyl chain of the three radicals mentioned can ultimately be interrupted by one to three oxygen ether atoms and can be substituted by phenyl or phenoxy, and cyclohexylloxy, phenoxy, halogen, hydroxyl or cyano. Alkyl radicals have, in general terms, one or two constituents. When alkyl radicals interrupted by oxygen ether atoms occur in the aforementioned formulas, alkyl radicals interrupted by one or two oxygen ether atoms are preferred. When substituted phenyl or pyridyl radicals occur in the aforementioned formulas, suitable substituents may be, for example, C 1 -C 8 alkyl, C 1 -C 8 alkoxy, halogen, especially chlorine or bromine, nitro or carbonyl.

Phenyl or pyridyl radicals have, in general terms, 1 to 3 substituents. Radicals R3, El, E2, Zl, Z2, Z4, Z5, Z¿ > and suitable Z7 are, for example, methyl, ethyl, prapila, isopropyl, butyl, isobutyl, sec-butyl or tert-butyl. R3, El, E2, Z1, Z3, Z4, 16 and Z7 are, additionally, each, for example, pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, 2-methyl, heptyl, octyl, -ethylhethyl, isaoctyl, nanoyl, isononyl, decyl, isodecyl, undecyl, dodecyl, tridecyl or isatrideci lo. (The names isooctyl, isononyl, isoyl ilo and isatrideci are common names and originate from the alcohols obtained by oxo synthesis (see Encyclopedia of Industrial Chemistry of Ull ann, 5th edition, vol. Al, pages 290 to 293, and vol. A10, pages 284 and 285).) R3, El, E2, Z1, Z3, Z4 and Z7 are each, in addition, for example, 2-methoxyetho, 2-eto-o-ti-lo, 2-propo? , 2-buto-ethyl, 2- or 3-metaxipropyla, 2- or 3-etho? Iprapi lo, 2- or 3-propoxyproxy, 2- or 3-butoxypropyl, 2- either 4-methobutyl, 2- or 4-ethoxybutyl, 2- or 4-butoxybutyl, 3,6-dioxyhepyl, 3,6-diox-octyl, 4,8-dioxanoni, 3 , 7-dio? Aocti lo, 3,7-dioxanonila, 4, 7-d ioxaoct i lo, 4, 7-dio? Anoni lo, 4,8-dioxadecila, 3,6,9-trioxadeci lo or 3, 6,9-trioxaundeci la. Zl, Z2 and Z6 are, in addition, each, for example, methoxy, ethoxy, propo i, isopropoxy, butoxy, isobutoxy or sec-buto ^ i. R3, El, E2 and Z? they are, in addition, each, for example, phenyl, 2-, 3-, or 4-methylphenyl, 2-, 3-, or 4-et-1-phenyl, 2-, -t- or 4-propyl. Ifeni lo, 2-, 3- or 4-? Soprop? Lfem lo, 2-, 3- or 4-butylphenyl, 2,4-d? Met 11 phen., 2-, 3- or 4-methoxypheni , 2-, 3- or 4-ethoxypheni, 2-, 3- or 4-metax? Fem lo, 2-, 3- or 4-ethoxyphenyl, 2-, 3- or 4-3 sobuta ?? feni 2, 4-d? methox? phenyl, 2-, 3- or 4-chlorophenol, 2,6-d? chlorophenol, 2- 3 or 4-mtophenyl, or 2-, 3-, or 4-c rbox? feni lo. Z3, Z4, Z ?, El and E2 are each, in addition, for example, cyclopentyl, cyclohexyl, or xclahep I. R3, Z3, Z4, El and E2 are each, also, for example, benzyl, 2-met i lbencí la, 1- or 2-feni lei lo, 2-h? drox? et i lo, 2- or 3-h? drox? prop? lo, 2-cyanoetyl, 2- or 3-c? Anopropyl, 2-acetyl loxyl, 2-, or 3-acetyl loxipropyl, 2- isobutyrimethyl, 2- or 3- ? sobut ip loxipropy lo, 2-methoxycarbom leti lo, 2- or 3-methox? carbon? propyl, 2-etho? icarbomleti lo, 2- or 3-etax? carbon? Ipropyl, 2- ethoxycarb sniloxieti lo, 2- or 3-methox? carbon? laxipropyl, 2-ethoxycarbonyloxyethyl, 2- or 3-ethoxycarbon? loxipropy lo, 2-butox? carban? loxie i lo, 2- or 3-butox? carbon? laxipropx lo, 2- < 2-fen? letoxJ arboni lo? i) et? lo, 2- 3 (2-f nor letaxxcarboni loxi) prop? What is 2- (2-ethoxyethoxycarbonyloxy) et? it or 2- or 3- (2-ethoxyethoxycarboni loxi) prop? the.

The and E2 are each also, for example, pyridyl, 2-, 3- or 4-met i I iridi lo, 2-, 3- or 4-metax ip i ri i la, farmyl, acetyl, propionyl, butyryl, is'obut iri lo, pentanoyl, hexanoyl, heptanoyl, ochatanoyl, 2-ei lhexanai lo, methoxycarboni, ethoxycarboni lo, propoxycarboni lo, isopropoxycarboni lo, butoxycarboni lo, isobutoxycarboni la, sec-butoxycarboni lo, met i lsul foni lo, etisul foni lo, propi lsulfoni lo, isopropi lsul foni lo, but i lsulfoni lo, iclopen i lsul foni la, cic lahex i lsulfoni lo, cyclohep i lsulfoni lo, feni Isulfoni lo, tol i lsulfoni lo, pyridi lsulfoni lo, benzoila, 2-, 3- or 4-meti lbenzoi lo, 2-, 3-? 4-methoxybenzoi lo, tien-2-i Icarboni lo or tien-3-i Icarboni lo. Zl is also, for example, meth i lsulfoni lamino, and the oni lamino, propi lsulfoni l mino, isopropi Isulfoni lamino, buti Isul foni lamino, mono- or dipropi laminsulsofni lamino, mono- or di isopropi laminsul foni lamino, mono- or dibuti leiminsuifoni lamino or (N-met il-N-eti l misul foni 1) amino. Z? > it is also, for example, fluorine, chlorine, bromine, benzyl, 2-met i lbe ci la, 2,4-dimet ilbenci lo, 2-methoxybenzyl, 2,4-dimetho-ibenz or, methylamino, ethylamino, prapilamino, isopropy lamino, butylated, pentyl, hexylamino, heptyl, amylamino, octylamine, 2-ylhexyl-lamino, methylthio, ethylthio, propyl, isopropyl lithium or bu ilia. Z3 and Z4 are each additionally, for example, to ilo or ilo metal.

R2 is, for example, methoxycarbonyl, ethanoalbonyl, propoxycarbonyl, isapropaxycarbonyl, butaxycarbonyl, pent i loxycarbonyl, hexyloxcarbonyl, acetyl, acetyl, prapionil, butyryl isabuthryl. Where E2 or Z3 and Z4, in each case together with the nitrogen atom that links them, are a satur 5-member hetaercyclic radical at either? > members which may also contain hetomatamines, suitable radicals of this type may be, for example, pyrrol idini lo, piperidinyl, orfolyl, piperazinyl or N- (Cl-C4 alkyl) ppiperazinyl. Preferred are pyridinone dyes of the formula I wherein X is CH. Preferred are also pyridane dyes of the formula I wherein R2 is cyano. Further preferred are pyridane dyes of the formula I wherein R 3 is C 1 -C 13 alkyl which may be interrupted by 1 to 3 oxygen ether atoms. Especially preferred are pyridane dyes of the formula I wherein R 3 is C 1 -C 6 alkyl which may be interrupted by 1 or 2 ether oxygen atoms. Pyridone dyes of the formula I are also preferred, where R 1 is a radical derived from a component of the benzene or thiazole series, especially a radical of the formula II i.

Particularly notable pyridone dyes are pyridone dyes of the formula where R3 is C1-C8 alkyl, 23 and Z4, independently of each other, are each C1-C8 alkyl substituted or unsubstituted by C1-C4 alkoxy, C1-C4 alkoxycarbany or phenylalkyl, or are each cyclopentyl, cyclohexyl or prop-1-en-3-ylo and Zó is C3-C10 alkyl or branched phenyl, especially branched C3-C8 alkyl. The pyridone dyes which are very especially notable are the pyridinone dyes of the formula wherein 16 is branched C3-C6 alkyl, especially branched C5 alkyl, and particularly neopentyl. Other very particularly remarkable pyridone dyes are pyridone dyes of the formula wherein, when Z3 and Z4 are each C1-C8 alkyl, the total number of carbrone atoms present in the two radicals Z3 and Z4 is at least 7, particulat least 8. The novel pyridone dyes of the formula I can be prepared by methods known per se.

For example, these pyridone dyes of the formula I wherein X is CH can be obtained by condensation of aldehydes of the formula III R ^ CHO ("i). where Rl has the meanings mentioned above, with trif luraromet i lpi ridona of formula IV CF3 where R2 and R3 each have the meanings mentioned above. These pyrirone dyes of the formula I wherein X is nitrogen can be obtained, for example, by condensation of nitroso compounds of the formula V Rl-HO (V > ' where R1 has the meanings mentioned above, or by oxidative coupling of the amino compounds of the formula IV R1- m * (VI), where Rl has the meanings mentioned above, with the trif luoro et i lpi idonas IV.

The intermedi for the preparation of the novel pyridone dyes are, in general terms, known per se. The present invention further rel to a process for the transfer of dyes from a substrto a plastic co paper by diffusion or sublimation with the aid of an energy source, comprising the use of a carrier on which they are loc. present one or more pyridone dyes of the formula I. For the preparation of the dye substr required for the novel process, the dyes of the formula I in a suitable organic solvent or in a mixture of solvents are processed with one or several binders, with or without addition of adjuvants to provide a printing ink. The latter contains the dyes of the formula I preferably in a dispersed molecular form. The printing ink can be applied to the inert substrby means of a knife applicator, and can be serr, for example, in the air or by using a hot air blower. Suitable organic solvents for the dyes of the formula I are, for example, solvents in which the solubility of the dyes of the formula I is greater than 1, greater than 5 '/. in weight at 20'C. Examples are ethanol propanol, isobutanol, tetrahydrofuran, methylene chloride, methylethyl ketone, cilcopentanone, iclohexanone, toluene, chlorobenzene and mixtures thereof. Suitable agglomerates are all resins or polymeric materials that are soluble in organic solvents and that can fix the dyes on the inert substrate in abrasion resistant form. The preferred binders are the binders which, after drying of the printing ink in the air, absorb the dyes in the form of a clear, transparent film, without visible crystallization of the dyes. Such binders are mentioned, for example, in US-A-5 132 438 or in the corresponding patent applications mentioned here. Other examples are saturated linear polyethers. Preferred binders are ethyl cellulose, ethylhydro-ethyl cellulose, polybutylene polymer, polyvinyl acetate, cellulose propionate and saturated linear lipid esters. The weight ratio between the binder and the dye is, in general, from 1: 1 to 10: 1. Suitable adjuvants are, for example, release agents according to that mentioned in US-A-5 132 438 or well in the corresponding patent applications mentioned here. Other examples are, in particular, organic additives which prevent the transfer dyes from crystallizing during storage or during the heating of the colored ink, for example cholesterol or vanillin. For example, suitable inert substrates are disclosed in US-A-5 132 438 or in the patent applications mentioned herein. The thickness of the dye substrate is, in general terms, from 3 to 30 μm. Suitable dye acceptor layers are, in principle, all thermosetting plastic layers having an affinity for the dyes to be transferred, for example polyesters or modified polycarbonates. Additional details in this context can be obtained, for example, in document US-A-5 132 438 or in the corresponding patent applications mentioned herein. The transfer is achieved by means of an energy source, for example, a laser or thermal printhead, and the latter must be able to heat up to a temperature greater than or equal to 300 ° C in such a way that the transfer of dye can be done in a time range ts O <; t < 15 sec. During this procedure, the dye migrates out of the transfer sheet and diffuses into the surface reversal of the receptor medium. The novel dyes of the formula I have performance characteristics that are advantageous in terms of dye transfer. They have a high solubility in the color ink (good compatibility with the binder, a high stability in the printing dye, a good transfer capacity, a high image stability (it is to go good resistance and good stability to environmental influences) , for example humidity, temperature or chemical products) allows a flexible color adaptation to the existing primary substrate colors, in the sense of an optimal trichromatic color (maximum possible brightness of primary or mixed colors and neutral black p ofundo). it has also found that synthetic materials can be colored or printed with benefit if they are treated with one or more novel colorants Synthetic materials are, for example, polystyrenes, polyamides or polycarbonates Particular examples are materials in a flexible form, such as, for example, fibers , yarns, twines, woven fabrics and woven fabrics of polyester, modified polyester, for example anionically modified liyester, polyester binding fabrics with cellulose, cotton, viscose or wool, or polia ida. The coloring and printing conditions are known per se. Colorations or impressions are obtained with good resistance, good level of brightness and excellent resistance to moisture, for example a good resistance to washing or to sweat.

The novel dyes can also be used to color keratin fibers, for example to dye the hair or to dye skins. The novel dyes of the formula I can also be used with advantage for the production of color filters, in accordance with what is described, for example, in EP-A-399 473. Finally, they can be used advantageously as dyes for the preparation of toners for electrophotography. The following examples illustrate the invention. A) PREPARATION EXAMPLE a) 128 g of potassium thiocyanate were initially added in 150 ml of acetone, and 185 ml of 3,3-dimethyl chloride was added at a temperature of 20 to 25 ° C. Agitation was carried out for 8 hours at room temperature, after which 234 ml of dibutyl lamin were added dropwise. After 4 hours, 120 g of ice and 142 ml of a 5% by weight sodium hydroxide solution were added, the temperature was maintained at a maximum of 40 * C. A solution of 132 g of clear acetic acid in 120 ml of water was added and the mixture was heated at 80 ° C for 8 hours. Phase separation was performed or > 0 ° C. The organic phase was diluted with methylene chloride and extracted several times by stirring with dilute hydrochloric acid and then with water. The organic phase was dried over sodium sulfate, after which the solvent was removed by distillation in a rotary evaporator. 311 g of a dark oil containing 69.5 '/ »(SC) of the compound of the formula" ^ CH2C (CH3) 3 were obtained.

(CH,) 2H b) A solution of 105 g of 2-dibutylamino-4- (2,2-dimethylpropi 1) thiazole (step a)) in 95 ml of N, N-dime 11 for a-ida was added dropwise, while cooled with water, to a solution of 441 ml of N, N-diethylformamide and 110 g of phosphorus oxychloride, said solution was prepared at a temperature of 0-5 ° C. The mixture was stirred for 2 hours, after which it was poured into ice / water, stirred overnight and then extracted with methyl acetate. The organic phase was then dried in sodium sulfate and the solvent was then removed by distillation in a rotary evaporator. 113. & g of a brown oil containing 83.5VÍ (BC) of the compound of the formula c) 654 g of 3-cyano-? -hydro were suspended? il-meti 1-4- tr i fluorome i llHp? pd? n ~ 2-one and 11.6 g of 2-d? but i lamino-4- (2,2-d? met? lprapi 1) -5-form ? 1 t azole (etaba b)) acetic anhydride at room temperature and then heated at 8 ° C for one hour. Pre-evaporated E3 that was removed on cooling was removed by filtration with suc ón, washed with water and methanol and recrystallized from ethyl acetate. 8.4 g (54.8 * / theoretical yield) of a crystalline compound or of the formula melting point: 169 ° C $ lambda ax (in CH2C12): 545 nm. 1H-NMP (C13, 250 MHz): delta = 8.02 (s; lH), 3.80 (t J 8 Hz5 2H), 3.58 (t, J * 8 Hz, 2H), 3.38 (s; 3H), 2.80 (s, 2H), 1.70 (m? 4H), 1.38 (m? 4H), 1.00 (s; 9H) , 0.95 (m, 6H). CHN 0 FS calculated 58.75 6.52 10.98 6.27 11.17 6.27 found 58.80 6.40 10. 0 6.30 11.20 6.30 EXAMPLE 6.34 g of 3-c? Ana-6-h? Drax? -l-met 11-4-tp f luoromet i llHp were suspended. ? pd-2-one and 4.37 g of 2-d? but? lane-4-phene 3 -5-rntrosotho-azole in 35 ml of acetic anhydride at room temperature and then heated to 80 ° C for 1 hour. The precipitate that separated upon cooling was removed by filtration with suction. It was washed with water and hexane and recpsltal i from ethyl acetate. 7.4 g (7.11 * / «of the theoretical level) of a 1 'blue crystalline compound was obtained to the formula TABLE 2 B) COLORING TRANSFER GENERAL METHOD: a) 10 g of dye are stirred in 100 g of a solution ÍOV, by weight of a binder of a mixture of methyl ethyl ketone / toluene / cyclohexanone (4.5: 2: 2 v / v / v), if necessary with brief heating at 80-90 ° C. The resulting printing ink is applied by means of a 6 μm spatula on a polyester film of 6 μt? of thickness, on the back of which a suitable slip layer has been agitated, and blow-dried for one minute with a hot air blower. Before I can i. Before printing the color ink, it must be dried additionally for at least 24 hours in the air since the residual solvents can negatively affect the printing process. b) The color ribbons are printed on commercial video printing paper (type VY-S of Hitachi) in a computer controlled experimental setup equipped with a commercial thermal print head. The energy output of the thermal print head is controlled by changing the voltage, the set pulse time is 7 s and only one pulse is being produced. The output energy is 0.7 to 2.0 mJ / point ,, Since the amplitude of the coloration is directly proportional to the energy supplied, it is possible to produce a wedge of color and evaluate it spectroscopically. The value W * (= energy in mJ for the extinction value l) is determined from the graph of the color depth against the energy supplied per heating element. The results obtained appear in Table 3 below. (In the data for Q *, the first value in each case refers to a er based on polyester and the second value in each case refers to a er based on pal ivini lb? Ti ral.) TABLE 3 No. of heat Q * (mJ / point) 1 0.76 0.76 2 1.01 1.12 3 1.02 1.16 4 1.01 1.10 5 1.58 1.34 6 0.80 0.82 7 1.01 1.12 8 .80 0.81 0.83 0.81 0.84 0.88 11 0.84 0.89 12 0.77 0.87 3 0.86 0.88 14 0.81 0.87 0.85 0.87 16 0.83 0.86 17 0.84 0.86 18 0.84 0.79 19 0.78 0.83 .0 0.80 0.77 21 0.75 0.78 22 1.08 23 1.08 24 1.04 1.01 25 0.95 26 1.18 27 0.97 0.94 c) COLORING APPLICATION METHOD A polyester fabric is introduced at a temperature of 55 * C in a staining bath containing V > of dye (based on the weight of the cloth), 1 g / 1 of the sodium salt of a condensate of naphthalene-2-sulfonic acid and formaldehyde and 0.5 ml / 1 of a buffer solution (pH 4.5). The bath was then heated to 130 ° C in the course of 30 minutes and maintained at this temperature for an additional 60 minutes. After cooling and washing, the cloth is cleaned by reduction for 30 minutes at 70 ° C in a bath containing 4 g / 1 of a solution of sodium hydroxide at 32% by weight, 2 g / 1 of sodium dithionite and 1 g / 1 of an adduct of 12 mol of ethylene oxide with 1 mol of olei lamina and then washed and dried. Bright red colorations were obtained which were very resistant to light and exhibited a good resistance to washing and sweating with the dyes of examples 1, 6 and 14. Example 1: X = 0.5, 0.75, 1.0 and 1.5 CA) Example 6: X = 0.1, 0.5, 0.75 (* /.) Example 14: X = 0.35, 0.5, 0.8 and 1.0 (%)

Claims

CLAIMS 1. A pyridone dye of the formula I
R * where X is nitrogen or CH, R1 is a 5-membered or 5-membered heterocyclic or carbacyclic radical, R2 is cyano, carbamoyl, C1-C6 alkoxycarbany or C1-C4 alkanoyl and R3 is C1-C13 alkyl, substituted or unsubstituted, and may be interrupted by the 3 oxygen ether atoms, either substituted or unsubstituted phenyl or a radical of the formula E1E3, where El and E2 are identical or different and, independently of each other, are each one hydrogen, substituted or unsubstituted C1-C13 alkyl and may be interrupted by the 3 oxygen ether atoms, or are each C5-C7 cycloalkyl, substituted or unsubstituted phenyl, substituted or unsubstituted pyridyl, C1-C13 alkanoyl unsubstituted or substituted, C1-C13 alkoxycarbonyl, substituted or unsubstituted C1-C13 alkylsulfonyl, C1-C7 cycloalkylsulfonyl, substituted or unsubstituted phenylsulfonyl, substituted or unsubstituted pyridyl sulfonyl, substituted or unsubstituted benzoyl, pyridyl carbonyl or thienicarbonyl or E1 and E2, together with the nitrogen atom linking them, are unsubstituted or unsubstituted or substituted by C1-C4 alkyl, phthalimido is unsubstituted or substituted by C1-C4 alkyl or a radical saturated 5-membered or 6-membered heterocyclic that may contain additional heteratans, excluding compounds where R 1 is a radical derived from 4-trir luoromethylpi lyrin as initial structure. 2. A pyridone dye according to claim 1, wherein X is CH.
3. A pyridone dye according to claim 1, wherein R2 is cyano.
4. A pyridone dye according to claim 1, wherein R3 is C1-C13 alkyl which may be interrupted by 1 to 3 oxygen ether atoms.
5. A pyridone dye according to claim 1, wherein R1 is a radical derived from a component of the benzene, indole, quinoline, nephthalene, pyrrole, thiazole, benzimidazole, benzothiazole, thiophene or pyridine series.
6. A conforming pyridone dye with claim 1, wherein R1 is a radical of the formula (lia) (Ilb) (lie) (lid) (II «) (Hf) (ig) (H) (Hi) ("j) where n is 0 or 1, Zl is hydrogen, C1-C13 alkyl which may be interrupted by 1 to 3 oxygen ether atoms, or is hydroxyl, C1-C4 alkoxy, alkylsulphonylamino C1-C4, mono- or either dialqui laminosul fani lamino C1-C4 or a radical -NHC0Z7 or else -NHC02Z7, where Z7 is phenyl, benzyl, tolyl or C1-C13 alkyl which may be interrupted by 1 to 3 oxygen ether atoms, • Z2 is hydrogen, C 1 -C 4 alkyl or C 1 -C 4 alkoxy, Z 3 and Z 4 are identical or different and, independently of each other, each one is hydrogen or substituted or unsubstituted C 1 -C 13 alkyl and can be interrupted by 1 to 3 The oxygen ether atoms are either C3-C4 alkenyl, C5-C7 cycloalkyl, phenylalanyl or, together with the nitrogen atom linking them, a 5-membered or 6-membered saturated heterocyclic radical which may contain additional heteroatoms, Z5 is hydrogen or C1-C4 alkyl and Z6 is hydrogen, halogen, alkyl C1-C13, substituted or unsubstituted phenjyl, substituted or unsubstituted benzyl, C5-C7 cycloalkyl, thienyl, hydroxyl, C1-C4 alkoxy, C1-C4 alkylthio or C1-C13 onoalkylamino.
7. A process for transferring dyes from a substrate to a plastic-coated paper by diffusion or sublimation with the aid of an energy source, comprising the use of a substrate on which one or more pyridone dyes are present. in accordance with claim i.
8. A process for coloring or printing synthetic materials, wherein the synthetic materials are treated with one or more pyridone dyes according to claim 1.