DE19701869A1 - Colour photographic material used in colour photographic films, etc. - Google Patents

Abstract

A photographic material, with a base and light-sensitive silver halide emulsion layer(s), contains a colour coupler and a dye stabiliser for the dye formed from the colour coupler by colour development. The coupler is a 4-hydroxybenzoxazole of formula (I) and the dye stabiliser is a 2-(benzotriazol-2-yl)- or 2-(tri-azin-2-yl)-phenol of formula (II), phenol derivative of formula (III) or N-heterocyclic compound of formula (IV). In (I), R<1>, R<2> = hydrogen (H) or a substituent; X = H, halogen or a group released in chromogenic development; and Y = a chemical bond, arylene, het-arylene or a group of the formula -NH-CO-, -NH-SO2-, -NH-CO-NH-, -NH-SO2-NH- or -NH-CO-O- linked to the 2-position of the oxazole ring. In (II), R<21-24> = H, alkyl, alkoxy, aryl, aryloxy, acyl or acylamino; and X<2> = a benzotriazol-2-yl or tri-azin-2-yl group. In (III), R<31> = H, alkyl, aryl or acyl; R<32-36> = as R<31>, halogen, nitro (NO2), cyano (CN), carboxyl (COOH), sulpho (-SO3H), -OR<31>, alkylthio, arylthio, acylamino or -N(R<37>)R<38>, provided that R<34> not = H or halogen if R<31> = H or acyl; R<37> = alkyl or aryl; and R<38> = H or R<37>. In (IV), R<41> = H, alkyl, alkoxy or acyl; R<42-45> = aryl or R<41>; and Q = a group containing a 5-8-membered ring.

Description

The invention relates to a photographic recording material with a new Combination of cyan couplers of formula I and dye stabilizers one of Formulas II, III and IV.

The cyan couplers used according to the invention are verbin compounds of the formula I (4-hydroxybenzoxazoles)

They are the subject of German Patent Application P 44 15 776.2. cyan coupler of the formula I provide in the chromogenic development cyan dyes with good Absorption properties (low side absorptions); the dark and light But stability leaves something to be desired.

The invention is based on the object, a color photographic recording indicate a chromium-green part in chromogenic development Color image with good absorption properties, as well as good dark storage stability and provides good light stability.

The invention is a color photographic recording material with a support and disposed thereon at least one photosensitive Silver halide emulsion layer containing a color coupler together with a Colorant stabilizer for the chromogenic development of the color coupler produced dye, characterized in that the color coupler corresponds to the formula I.

in which mean:
R¹, R² is H or a substituent;
XH, a halogen atom or a group cleavable in chromogenic development;
Y is a chemical bond, an arylene radical, a hetaryl radical or one of the following groups which is bonded via one of its N atoms to the 2-position of the oxazole ring: -NH-CO-, NH-SO₂-, -NH-CO-NH , -NH-SO₂-NH- and -NH-CO-O-,
and that the dye stabilizer corresponds to one of the formulas II, III and IV

in which mean:
R²¹ to R²⁴ (independently of one another) are H, alkyl, alkoxy, aryl, aryloxy, acyl or acylamino;
X² is a benzotriazol-2-yl or triazin-2-yl radical;
R³¹ is H, alkyl, aryl or acyl;
R³² to R³⁶ (independently of one another) have a radical such as R³¹ or halogen, -NO₂, -CN, -COOH, -SO₃H, -OR³¹, alkylthio, arylthio, acylamino, or -N (R³⁷) R³⁸, where R³⁴ does not denote H or halogen if R³¹ is H or acyl;
R³⁷ is alkyl or aryl;
R³⁸H or a radical such as R³⁷;
R⁴¹ is H, alkyl, alkoxy or acyl;
R⁴² to R⁴⁵ (independently of one another) aryl or a radical such as R⁴¹;
Q the neces sary to complete a 5- to 8-membered ring remainder.

In Formula I, there is no particular limitation on the substituents R¹ and R². Typical examples are halogen, -NO₂, -COOH, alkyl, alkenyl, cycloalkyl, Cycloalkenyl, alkynyl, bicyclic or polycyclic hydrocarbon radicals, Aryl, heterocyclyl, alkoxy, aryloxy, acyloxy, sulphonyloxy, heterocyclyloxy, Silyloxy, alkylthio, arylthio, heterocyclylthio, amino, alkylamino, dialkylamino, Cycloamino, arylamino, acylamino, imido, ureido, thioureido, sulfonamido, sul famoylamino, acyl, sulfonyl, sulfinyl, sulfamoyl, phosphonyl, phoshinyl, however with the proviso that R¹ is not halogen.

By way of example, halogen represented or contained in R¹ or R² is, for example Fluror, chlorine or bromine.

By R¹ or R² shown or contained therein alkyl substituents here preferably radicals having 1-32 C atoms, straight-chain or branched, unsub substituted or substituted, e.g. Substituted with hydroxyl, aryl, alkoxy, aryloxy or acyl. Typical examples are methyl, ethyl, propyl, isopropyl, butyl, Tertiary butyl, tertiary amyl, hexyl, octyl, tertiary octyl, dodecyl, hexadecyl, Heptadecyl, 2-phenoxypropyl, ω-penoxypropyl, ω-benzoylpropyl, 2-phenoxy pentyl, 2-phenoxydodecyl.  

By alkenyl substituents represented by R¹ or R² or contained therein ent keep 2-32 C-atoms; the alkenyl substituent may be straight or branched his.

Cycloalkyl and cyclo represented by or represented by R¹ and R², respectively Alkenyl substituents contain 3-12 C atoms, preferably 5-7 C atoms. Typical cycloalkyl radicals are cyclopentyl and cyclohexyl.

Bicyclic or polycyclic compounds represented by or represented by R¹ and R², respectively For example, hydrocarbon radicals are spiro substituents such as spiro [3,3] heptan-1-yl or bridged hydrocarbon radicals such as bicyclo [2,2,1] heptan-1-yl, Tricyclo [3,2,1,1] decane-1-yl or 7,7-dimethylbicyclo [2,2,1] heptan-1-yl.

Aryl substituents represented by R¹ or R² or contained therein are included For example, phenyl and substituted phenyl, z. With halogen, cyan, Carboxy, alkyl, cycloalkyl, alkoxy, sulfamoyl, alkylthio and / or acylamino substituted phenyl radicals.

Heterocyclic substituents represented by R¹ or R² or contained therein are, for example, 5- to 7-membered heterocycles; typical examples are 2-furyl, 2-thienyl, 2-pyrimidinyl, 2-benzthiazolyl, 1-pyrrolyl, 1-tetrazolyl. Heterocyclyl-oxy Substituents are preferably 5- or 7-membered ring bonded via an O atom. Heterocycles; typical examples are 3,4,5,6-tetrahydropyranyl-2-oxy, 1-Phenyltetrazoly-5-oxy. Heterocyclylthio substituents are preferably over an S atom-bonded 5 to 7-membered heterocycles; typical examples are 2-pyridylthio, 2-benzthiazolylthio, 2,4-diphenoxy-1,3,5-triazinyl-6-thio.

Cycloamino substituents represented by R¹ or R² or contained therein For example, pyrrolidino, piperidino, morpholino, thiomorpholino, S, S-di oxothiomorpholino or piperazino.

By R¹ or R² represented or contained therein acyl substituents are of an organic carboxylic acid, a carbamic acid or a carbonic acid half derived ester. Examples are alkylcarbonyl, arylcarbonyl, hetarylcarbonyl, Carbamoyl, alkylcarbamoyl, arylcarbamoyl, N-alkyl-N-aryl-carbamoyl, hetaryl carbamoyl, alkoxycarbonyl. Acyloxy substituents are, for example, alkylcar bonyloxy, arylcarbonyloxy, hetarylcarbonyloxy, alkoxycarbonyloxy, carbamoyl  oxy. Acylamino substituents are, for example, alkylcarbonylamino, arylcar bonylamino, hetarylcarbonylamino, ureido.

By R¹ or R² represented or contained therein sulfonyl substituents z. As any type of alkylsulfonyl, arylsulfonyl or hetarylsulfonyl. sulfonamido Substituents are for example Alkylsulfonamido, Arylsulfonymido or Het arylsulfonamido.

By R¹ or R² shown or contained therein sulfinyl substituents are z. For example, any type of alkylsulfinyl, arylsulfinyl or hetarylsulfinyl.

By R¹ or R² shown or contained therein sulfamoyl substituents z. For example, any type of alkylsulfamoyl, arylsulfamoyl or hetarylsulfamoyl. Sulfamoylamino substituents are, for example, alkylsulfamoylamino or Arylsulfamoylamino.

By R¹ or R² represented or contained therein phosphonyl substituent are z. For example, any type of alkylphosphonyl, arylphosphonyl, alkoxyphosphonyl or Aryloxy phosphonyl.

By R¹ or R² shown or contained therein ureido substituents z. As any type of alkylureido, arylureido or hetarylureido.

By R¹ or R² represented or contained therein imido substituents are, for. B. Succinimido, 3-heptadecylsuccinimido, glutarimido or phthalimido.

A residue X which can be split off by X in chromogenic development may be, for example: H, a halogen atom such as Cl, Br or F, substituents such as: alkoxy, aryloxy, heterocyclyloxy, acyloxy, sulphonyloxy, alkoxycarbonyl oxy, aryloxycarbonyloxy, alkyloxalyloxy, alkoxyoxalyloxy, alkylthio, arylthio, Heterocyclylthio, alkyloxythiocarbonylthio, acylamino, sulfonamido, an N-hal tiger heterocycle, which is linked via an N atom with the coupler radical, Alkoxycarbonylamino, aryloxycarbonylamino, carboxyl, -N = N-aryl.

Examples of cyan couplers of the formula I used according to the invention are in listed below.

A in the formulas II, III and IV by one of the radicals R²¹ to R⁴⁵ or Q represented or contained therein alkyl radical can straight-chain, branched or be cyclic and optionally further substituted. One through one of the leftovers R²¹ to R⁴⁵ or Q shown or included therein aryl radical may also be further substituted. Examples of suitable substituents on alkyl or Aryl radicals in R²¹ to R⁴⁵ or Q are the radicals mentioned for R³², in particular Halogen, hydroxy, alkoxy, aryloxy, alkoxycarbonyl, acyloxy and acylamino.

By R²¹ to R⁴⁵ or Q shown or contained therein acyl substituents are from an aliphatic or aromatic carboxylic acid, carbamic acid, Sulfonic acid, sulfinic acid, sulfamic acid, phosphoric acid, phosphonic acid, Derived phosphorous acid or a carbonic acid half ester.  

A triazin-2-yl radical represented by X.sup.2 in formula II is in particular a 1,3,5- Triazin-2-yl radical. The benzotriazol-2-yl and triazin-2-yl groups represented by X² can carry further substituents, for. As halogen, alkoxy, aryloxy or Aryl.

In preferred embodiments of the invention are referred to below bene compounds of the formulas II, III and IV as a stabilizer ver applies:

Formula II: X² = benzotriazol-2-yl; R 21 = H, alkyl; R²², R²⁴ = H; R 23 = alkyl;
Formula II: X² = triazin-2-yl; R²¹, R²³, R²⁴ = H; R²² = alkoxy;
Formula III: R³¹ = H, alkyl; R³² to R³⁶ = H, alkyl, -OH, alkoxy, acylamino, acyl;
Formula IV: Q completes a 6-ring; R⁴², R⁴⁴ = H, alkyl; R⁴³, R⁴⁵ = alkyl.

In particularly preferred embodiments of the invention are hereinafter circumscribed compounds of the formulas III and IV as a dye stabilizer used:

Formula III: R³¹ = H; R³² to R³⁶ = H, alkyl, acylamino, acyl;
Formula IV: R⁴¹ = alkyl, acyl.

Examples of compounds according to the invention of the formulas II, III and IV are

The color photographic recording material according to the invention contains at least a photosensitive silver halide emulsion layer and preferably an Ab follow several such photosensitive silver halide emulsion layers and optionally further auxiliary layers such as in particular protective layers and zwi the photosensitive layers arranged non-photosensitive Binder layers, wherein according to the present invention, at least one of existing photosensitive silver halide emulsion layers a cyan coupler of the formula I in combination with at least one compound of one of Formulas II, III and IV is assigned.

The compounds of the formulas II, III and IV used according to the invention act primarily as a light stabilizer and / or Dark Lagersta stabilizer (dye stabilizer), d. H. from the color coupler of the formula I. azomethine dyes formed in chromogenic development exhibit Presence of said compounds to a considerably increased stability. In addition, the compounds mentioned can also partially the function of a Apply oil former for the color coupler, d. H. they may be too together with other known oil formers as Kupplerlösungsmittel for Cyan couplers of the formula I can be used.

The addition to the casting solutions for the relevant layer takes place in the üb way. The concentration in the finished cast layer is for the Cyan coupler of the formula I 20 to 2000 mg / m², preferably 100 to 1500 mg / m²  and for the stabilizers 10 to 2000 mg / m², preferably 50 to 1500 mg / m².

Examples of color photographic materials are color negative films, color reversal films, color positive films, color photographic paper, color reversal photographic paper, color-sensitive materials for the color diffusion transfer method or the Sil berfarbbleich method.

The photographic materials consist of a support on which at least one photosensitive silver halide emulsion layer is applied. As a carrier In particular, thin films and films are suitable. An overview of carriers materials and on their front and back applied auxiliary layers is in Research Disclosure 37254, Part 1 (1995), p. 285.

The color photographic materials usually contain at least one red each sensitive, green-sensitive and blue-sensitive silver halide emulsions layer and optionally intermediate layers and protective layers.

Depending on the type of photographic material, these layers may be arranged differently. This is illustrated for the main products:
Color photographic films such as color negative films and color reversal films have 2 or 3 red-sensitive, cyan silver halide emulsion layers, 2 or 3 green-sensitive, magenta-coupling silver halide emulsion layers and 2 or 3 blue-sensitive yellow coupling silver halide emulsion layers on the support 2 in the order given below. The layers of the same spectral sensitivity differ in their photographic sensitivity, with the less sensitive sublayers generally being arranged closer to the carrier than the higher sensitive sublayers.

Between the green-sensitive and blue-sensitive layers is more common a yellow filter layer attached, the blue light prevents it, in the to reach underlying layers.

The possibilities of different layer arrangements and their off effects on the photographic properties are described in J. Int. Rec. Mats., 1994, Vol. 22, pages 183-193.  

Color photographic paper, which is generally much less sensitive to light as a color photographic film, has the order given below usually a blue-sensitive, yellow-coupling silver halo on the support genisemulsion layer, a green sensitive, purplish coupling silver halide emulsion layer and a red-sensitive, cyan silver halide emulsion layer on; the yellow filter layer can be omitted.

Deviations from the number and arrangement of the photosensitive layers can to achieve certain results. For example, you can all highly sensitive layers to a layer package and all low-sensitivity layers to another layer package in a photographic film summarized to increase the sensitivity (DE 25 30 645).

Essential constituents of the photographic emulsion layers are binders, Silver halide grains and color couplers.

Information on suitable binders can be found in Research Disclosure 37254, Part 2 (1995), p. 286.

Information on suitable silver halide emulsions, their preparation, ripening, Stabilization and spectral sensitization including appropriate spectral sensitizers can be found in Research Disclosure 37254, Part 3 (1995), p. 286 and in Research Disclosure 37038, Part XV (1995), p. 89.

Photographic materials with camera sensitivity usually include Sil Berbromidiodidemulsionen, which may also contain small amounts of silver chloride can contain. Photographic copying materials contain either silver chloride bromide emulsions containing up to 80 mol% AgBr or silver chloride bromide emulsions with over 95 mol% AgCl.

For color couplers see Research Disclosure 37254, part 4 (1995), p. 288 and Research Disclosure 37038, Part II (1995), p. 80. The maximum absorption from the couplers and the color developer oxidation product formed dyes is preferably in the following areas: Yellow coupler 430 to 460 nm, magenta coupler 540 to 560 nm, cyan coupler 630 up to 700 nm.  

In color photographic films, to improve sensitivity, Graininess, sharpness and color separation are often used in the compounds Reaction with the developer oxidation product release compounds, the foto are graphically effective, z. B. DIR couplers which are a development inhibitor columns.

Information on such compounds, in particular couplers, can be found in Research Disclosure 37254, Part 5 (1995), p. 290 and in Research Disclosure 37038, Part XIV (1995), p. 86.

Most hydrophobic color couplers, but also other hydrophobic components the layers are usually in high boiling organic solvents dissolved or dispersed. These solutions or dispersions are then in a aqueous binder solution (usually gelatin solution) emulsified and are after drying the layers as fine droplets (0.05 to 0.8 microns through knife) in the layers.

Suitable high-boiling organic solvents, methods for incorporation into the layers of a photographic material and other methods, chemical To introduce compounds into photographic layers can be found in Research Disclosure 37254, Part 6 (1995), p. 292.

The usually between layers of different spectral sensitivity arranged non-photosensitive intermediate layers may contain agents, the unwanted diffusion of developer oxidation products from a photosensitive in another photosensitive layer with different prevent spectral sensitization.

Suitable compounds (white couplers, scavengers or EOP scavengers) can be found in Research Disclosure 37254, Part 7 (1995), p. 292 and in Research Disclosure 37038, Part III (1995), p. 84.

The photographic material may also contain UV light absorbing compounds brighteners, spacers, filter dyes, formalin scavengers, light stabilizers, antioxidants, D _min dyes, additives for improving the dye, coupler and white stability and for reducing the color fog, plasticizers (lattices), biocides and other things included.

Suitable compounds are found in Research Disclosure 37254, Part 8 (1995), P. 292 and Research Disclosure 37038, parts IV, V, VI, VII, X, XI and XIII (1995), p. 84 ff.

The layers of color photographic materials are usually cured, i. H., the binder used, preferably gelatin, by suitable crosslinked chemical processes.

Suitable hardener substances can be found in Research Disclosure 37254, part 9 (1995), p. 294 and Research Disclosure 37038, Part XII (1995), p. 86.

After imagewise exposure, color photographic materials become their character ter accordingly processed according to different methods. Details of the Procedures and required chemicals are in Research Disclosure 37254, Part 10 (1995), p. 294 and Research Disclosure 37038, parts XVI to XXIII (1995), p. 95 et seq., Together with exemplary materials.

example 1

A multilayer color photographic recording material (Sample 1) was made by placing on a substrate made of both sides with polyethylene coated paper, the following layers in the order given were applied. All quantities refer to 1 m², the amount of silver is indicated as AgNO₃:

Layer 1 (substrate layer):
0.10 g of gelatin

Layer 2 (blue-sensitive layer):
blue-sensitive silver halide emulsion (99.5 mol% chloride, 0.5 mol% bromide, average grain diameter 0.9 microns) from 0.50 g AgNO₃, with
1.25 g of gelatin
0.42 g yellow coupler XY-1
0.18 g yellow coupler XY-2
0.50 g of tricresyl phosphate (TKP)
0.10 g stabilizer XST-1
0.10 g stabilizer XST-2
0.70 mg blue sensitizer XBS-1
0.30 mg stabilizer XST-3

Layer 3 (intermediate layer):
1.10 g of gelatin
0.06 g of oxform scavenger XSC-1
0.06 g of oxform scavenger XSC-2
0.12 g TKP

Layer 4 (green-sensitive layer):
green-sensitive silver halide emulsion (99.5 mol% chloride, 0.5 mol% bromide, mean grain diameter 0.47 μm) from 0.40 g AgNO₃, with
0.77 g of gelatin
0.41 g magenta coupler XM-1
0.06 g stabilizer XST-4
0.12 g of oxform scavenger XSC-2
0.34 g of dibutyl phthalate (DBP)
0.70 mg green sensitizer XGS-1
0.50 mg stabilizer XST-5

Layer 5 (UV protection layer):
1.15 g of gelatin
0.50 g UV absorber XUV-1
0.10 g UV absorber XUV-2
0.03 g of oxform scavenger XSC-1
0.03 g of oxform scavenger XSC-2
0.35 g of diisononyl adipate

Layer 6 (red-sensitive layer):
red-sensitive silver halide emulsion (99.5 mol% chloride, 0.5 mol% bromide, average grain diameter 0.5 microns) from 0.30 g AgNO₃, with
1.0 g gelatin
0.46 g of cyan coupler I-53
0.46 g TKP
0.03 mg red sensitizer XRS-1
0.60 mg stabilizer XST-6

Layer 7 (UV protection layer):
0.35 g of gelatin
0.15 g UV absorber XUV-1
0.03 g UV absorber XUV-2
0.09 g TKP

Layer 8 (protective layer):
0.90 g of gelatin
0.05 g whitener XWT-1
0.07 g of stain (PVP)
1.20 mg of silicone oil
2.50 mg spacer (polymethylmethacrylate, average particle size 0.8 μm)
0.30 g of hardener XM-1

Compounds used in Example 1:

The color photographic material is characterized by a cyan color Zugsfilter and exposed a step wedge.

The processing baths were prepared according to the following procedure:

Color developer solution (CD) Tetraethylene glycol | 20.0 g N, N-diethyl 4.0 g (N-ethyl-N- (2-methanesulfonamido) ethyl)) - 4-amino-3-methylbenzene-sulfa-t 5.0 g potassium 0.2 g potassium carbonate 30.0 g polymaleic 2.5 g hydroxyethane 0.2 g Whitener (4,4'-diaminostilb type) 2.0 g potassium 0.02 g

Make up to 1000 ml with water, pH with KOH or H₂SO₄ to pH = 10.2 to adjust.

Bleach-fix solution (BX) Ammonium thiosulphate | 75.0 g sodium bisulfite 13.5 g Ethylenediaminetetraacetic acid (Fe-NH₄-salt) 45.0 g

Make up to 1000 ml with water, pH with ammonia (25%) or vinegar acid to pH 6.0.

Subsequently, the gb and pp secondary densities at a bg density of D = 1.0 determined. In addition, the sample with the light will turn on daylight standardized XENON lamp irradiated (20 m lux.h) and 42 days at 85 ° C, 60% rel. Damp stored dark. After that, in both cases the percentage Density determined (Table 1).

Samples 2 to 10

Samples 2 to 10 are prepared, processed and treated as sample 1 with the difference that as indicated in Table 1, the layer 6 a (or several compounds of one of the formulas II, III and IV in an amount of 0.23 g was added and / or the coupler I-53 by one of the couplers I-56 and I-59 has been replaced.

As can be seen from Table 1, the inventive compounds of the Formula II, III or IV, the light and dark storage stability of the invention Cyan coupler significantly improved and the secondary densities favorably influenced.  

Example 2 Samples 11 to 22

Samples 11 to 22 are made as Sample 1 with the difference as indicated in Table 2, the layer 6 is a compound of one of the formulas II, III and IV were added in an amount of 0.20 g and / or one of Comparative Compounds V-1, V-2 and V-3, coupler I-1 by 0.33 g of one of in Table 2 couplers I-54, I-55 and I-57 was replaced (Silver order lowered to 0.24 g!) And that the layer 4 together as follows is set:

Layer 4 (green-sensitive layer)
green sensitized silver halide emulsion (99.5 mole% chloride, 0.5 mole% bromide, average grain diameter 0.47 μm)
0.28 g of AgNO₃ with
0.88 g of gelatin
0.28 g magenta coupler XM-2
0.20 g Stabilizer XST-7
0.10 g stabilizer XST-8
0.30 g of dibutyl adipate
0.20 g isotridecanol
0.55 mg green sensitizer XGS-1
0.38 mg stabilizer XST-5.

Compounds used in Example 2 are XM-2, XST-7, XST-8

The samples are then exposed as described in Example 1, processed, irradiated and stored dark (Table 2).  

Table 2

(V: comparison, E: according to the invention)

As Table 2 shows, the compounds of the invention improve the formulas II, III and IV, the dye stability significantly stronger than the Vergleichsverbin tions that are in part even ineffective.

Claims (5)

A color photographic recording material having a support and having thereon at least one light-sensitive silver halide emulsion layer containing a color coupler together with a dye stabilizer for the dye formed in the chromogenic development from the color coupler, characterized in that the color coupler is of the formula I. in which mean:
R¹, R² is H or a substituent;
XH, a halogen atom or a group cleavable in chromogenic development;
Y is a chemical bond, an arylene radical, a hetaryl radical or one of the following groups which is bonded via one of its N atoms to the 2-position of the oxazole ring: -NH-CO-, -NH-SO₂-, -NH-CO -NH-, -NH-SO₂-NH- and -NH-CO-O-,
and that the dye stabilizer corresponds to one of the formulas II, III and IV in which mean:
R²¹ to R²⁴ (independently of one another) are H, alkyl, alkoxy, aryl, aryloxy, acyl or acylamino;
X² is a benzotriazol-2-yl or triazin-2-yl radical;
R³¹ is H, alkyl, aryl or acyl;
R³² to R³⁶ (independently of one another) have a radical such as R³¹ or halogen, -NO₂, -CN, -COOH, -SO₃H, -OR³¹, alkylthio, arylthio, acylamino, or -N (R³⁷) R³⁸, where R³⁴ is not H or halo when R³¹ is H or acyl;
R³⁷ is alkyl or aryl;
R³⁸H or a radical such as R³⁷;
R⁴¹ is H, alkyl, alkoxy or acyl;
R⁴² to R⁴⁵ (independently of one another) aryl or a radical such as R⁴¹;
Q is the radical necessary to complete a 5- to 8-membered ring. 2. Recording material according to claim 1 with a dye stabilizer of Formula II, characterized in that X² is benzotriazol-2-yl, R²¹ for H or alkyl, R²² and R²⁴ is H and R²³ is alkyl. 3. Recording material according to claim 1 with a dye stabilizer of Formula II, characterized in that X² represents triazin-2-yl, R²¹, R²³ and R²⁴ is H and R²² is alkoxyl. 4. Recording material according to claim 1 with a dye stabilizer of Formula III, characterized in that R³¹ is H or alkyl and R³² to R³⁶ is H, alkyl, -OH, alkoxy, acylamino or acyl.   5. A recording material according to claim 1 with a dye stabilizer of Formula IV, characterized in that Q is a remainder to complete represents a 6-membered ring, R⁴² and R⁴⁴ stand for H or alkyl and R⁴³ and R⁴⁵ are alkyl.