EP0607801B1 - Photographic colour recording material - Google Patents

Description

The invention relates to a color photographic recording material with an expanded range of gradations in Range of maximum densities and thus one clearly improved tracing at high densities at the same time excellent color separation.

A lack of differentiation in the red tones is one Weakness of most color negative papers on the market. This weakness is particularly noticeable if films with very high inter-image effects and used very high color saturation and then copied onto conventional color negative paper become.

A certain improvement of this shortcoming will be according to EP 304 297, US 4 806 460 and US 5 084 374 that with a color photographic material with a first and a second silver halide emulsion layer, those for a first and a second area of the visible spectrum are sensitized and each color-forming couplers contain the second emulsion layer to a limited extent even for the first Range of the visible spectrum is sensitized. Contains e.g. the red-sensitive layer additionally a green sensitizer, so be in the purple area Instead of 11 previously developed 15 visible levels. Color photographic materials are usually for blue light, green light and red light sensitized. This applies in particular to print materials. For reasons of print compatibility (color papers of different origins must be made with negatives from Film correct colors in different origins reproduce) are print materials in the blue sensitive Range at about 480 nm, in the green sensitive range at about 550 nm and in the red-sensitive region at about 700 nm sensitized.

In the given example, the red-sensitive one Layer to a small extent also for the wavelength range around 550 nm with additional sensitivity to green or also for the wavelength range of 480 nm additional sensitivity to blue made sensitive.

This measure, as described, for example a secondary density of a different color in the purple area, e.g. Teal produced, but only in areas higher Density. In areas of high red density, the eye picks up this false color density not as color distortion, but true as a deepening of the main color. However, it can the measure can only be used for red tones without a color distortion is actually visible. The However, the number of additionally obtained gradation levels is not yet sufficient. It is also disadvantageous that pure purple and yellow tones, depending on the type of additional Sensitization to be falsified.

The object of the present invention is to provide of a color photographic material that one extended range of gradations for the color separations in the Range of maximum densities and thus a clear has improved tracing at high densities, which is also characterized by great color purity, especially in purple or yellow.

This object is achieved in that with a color photographic material with at least a cyan coupling containing a red sensitizer Silver halide emulsion layer, at least a purple coupling containing a green sensitizer Silver halide emulsion layer and at least a yellow coupling containing a blue sensitizer Silver halide emulsion layer the least a blue sensitive silver halide emulsion layer contains another spectral sensitizer, the Sensitization maximum between the sensitization maxima the red and green sensitive and / or the at least a red sensitive silver halide emulsion layer contains another spectral sensitizer, its sensitization maximum between the sensitization maxima the green and blue sensitive silver halide emulsion layer lies. Preferably that is Sensitization maximum this as a "gap sensitizer" (LS) designated dye by at least 15 nm from the sensitization maxima of the green or blue sensitizers and at least 30 nm from the sensitization maximum of the red sensitizer removed.

The sensitization maximum is on the finished material certainly. The material that the gap sensitizer contains, with an otherwise identical material compared, which does not contain the gap sensitizer. The additionally occurring absorption maximum is the sensitization maximum of the gap sensitizer.

The additional sensitizer can be used in any amount, preferably in an amount of 0.01 to 3 µmol / m ² .

For example, a blue-sensitive layer (λ _max at 480 nm) can additionally be sensitized for the range 580 to 650 nm and a red-sensitive layer (λ _max at 700 nm) for the range 495 to 530 nm. The red-sensitive layer is preferably additionally sensitized for the range 495 to 530 nm, in particular 495 to 515 nm.

The one according to the invention is particularly preferred Material is a material specified in the Order on a support at least one blue sensitive, containing at least one yellow coupler Silver halide emulsion layer, an intermediate layer, at least one green sensitive, at least one Silver halide emulsion layer containing magenta couplers, an intermediate layer, at least one red-sensitive, containing at least one cyan coupler Silver halide emulsion layer and at least contains a protective layer, characterized in that the red sensitive silver halide emulsion layer in the manner according to the invention additionally for the area from 495 to 515 nm is sensitized.

The gap sensitizer is added to the emulsion preferably after chemical ripening.

As silver halides of the color coupler-containing silver halide emulsion layers come AgBr, AgBrCl, AgBrClI and AgCl into consideration.

The silver halides preferably contain all photosensitive Layers at least 80 mole% chloride, in particular 95 to 100 mol% of chloride, 0 to 5 mol% Bromide and 0 to 1 mol% iodide. The silver halide emulsions can work directly positive or preferably be negative working emulsions.

The silver halide can be predominantly compact Act crystals that e.g. regular cubic or are octahedral or can have transitional forms. However, twins, e.g. platelet-shaped Crystals are present, their average ratio from diameter to thickness preferably at least 5: 1, wherein the diameter of a grain is defined as the Diameter of a circle with a circle content accordingly the projected area of the grain. The Layers can also be tabular silver halide crystals in which the ratio of Diameter to thickness is greater than 5: 1, e.g. 12: 1 to 30: 1.

The silver halide grains can also have one multiple have layered grain structure, in the simplest case with an inner and an outer grain area (core / shell), the halide composition and / or other Modifications such as Endowments of the individual Grain areas are different. The middle The grain size of the emulsions is preferably between 0.2 µm and 2.0 µm, the grain size distribution can be both be homo- and heterodisperse. The emulsions can in addition to the silver halide, organic silver salts included, e.g. Silver benzotriazolate or silver behenate.

Two or more types of silver halide emulsions, which are manufactured separately as Mixture can be used.

The photographic emulsions can be different Methods (e.g. P. Glafkides, Chimie et Physique Photographique, Paul Montel, Paris (1967), G.F. Duffin, Photographic Emulsion Chemistry, The Focal Press, London (1966), V.L. Zelikman et al., Making and Coating Photographic Emulsion, The Focal Press, London (1966) soluble silver salts and soluble halides become.

The silver halide is preferably precipitated in Presence of the binder, e.g. the gelatin and can carried out in the acidic, neutral or alkaline pH range are, preferably silver halide complexing agents can also be used. The latter belong e.g. Ammonia, thioether, imidazole, ammonium thiocyanate or excess halide. The merge the water-soluble silver salts and the halides is carried out one after the other after the single-jet or simultaneously using the double-jet method or by any combination of both methods. Prefers is the dosage with increasing inflow rates, the "critical" feed rate at which barely no new germs are created, not exceeded should. The pAg range can fall into vary wide limits, preferably the so-called pAg-controlled method used in which a certain pAg kept constant or a defined one pAg profile is traversed during the precipitation. In addition to the preferable precipitation with excess halide but also the so-called inverse precipitation with excess silver ions possible. Except through precipitation, the Silver halide crystals also through physical ripening (Eastern forest ripening), in the presence of excess Halide and / or silver halide complexing agents to grow. The growth of the emulsion grains can even predominantly by Ostwald ripening, preferably a fine-grained, so-called Lippmann emulsion, mixed with a less soluble emulsion and is redeemed on the latter.

The silver halide grains can be precipitated in the presence of "growth modifiers" are substances that are influence the growth so that special grain shapes and grain surfaces (e.g. 111 surfaces with AgCl) arise.

During precipitation and / or physical ripening The silver halide grains can also contain salts or complexes of elements of group 8, 1b, 2b, 3a, 4a and 5a of Periodic table of the elements for doping the silver halides be used.

The precipitation can also be carried out in the presence of sensitizing dyes respectively. Complexing agent and / or dyes can be any Deactivate the point in time, e.g. by changing the pH or by an oxidative treatment.

Gelatin is preferably used as the binder. However, this can be done in whole or in part by others synthetic, semi-synthetic or natural occurring polymers are replaced. Synthetic Gelatin substitutes are, for example, polyvinyl alcohol, Poly-N-vinyl pyrolidone, polyacrylamides, polyacrylic acid and their derivatives, especially their Copolymers. Naturally occurring gelatin substitutes are other proteins such as Albumin or casein, cellulose, chitins, chitosans, Sugar, starch or alginates. Semi-synthetic gelatin substitutes are usually modified natural products. Cellulose derivatives such as hydroxyalkyl cellulose, Carboxymethyl cellulose and phthalyl cellulose as well Gelatin derivatives by reaction with alkylation or Acylating agents or by grafting on polymerizable monomers have been obtained Examples of this.

The binders should have a sufficient amount of functional groups so that by implementation sufficiently resistant with suitable hardening agents Layers can be created. Such functional Groups are especially amino groups, however also carboxyl groups, hydroxyl groups and active methylene groups.

The gelatin which is preferably used can be acidic or alkaline digestion. The production such gelatin is described, for example, in The Science and Technology of Gelatine, published by A.G. Ward and A. Courts, Academic Press 1977, page 295 ff. The gelatin used in each case should have the lowest possible photographic content contain active impurities (inert gelatine). High viscosity, low swelling gelatins are particularly advantageous. The gelatin can partially or be completely oxidized.

After crystal formation is complete or already closed the soluble salts are removed at an earlier point in time removed from the emulsion, e.g. by pasta and washing, by flaking and washing, by ultrafiltration or through ion exchangers.

The photographic emulsions may contain compounds to prevent fogging or to stabilize the photographic function during production, storage or photographic processing.
Azaindenes are particularly suitable, preferably tetra- and pentaazaindenes, in particular those which are substituted by hydroxyl or amino groups. Such connections are for example from Birr, Z. Wiss. Phot. 47 (1952), pp. 2-58. Salts of metals, aromatic sulfonic or sulfinic acids such as benzenesulfinic acid, or nitrogen-containing heterocycles such as nitrobenzimidazole, nitroindazole, (subst.) Benzotriazoles or benzothiazolium salts can also be used as antifoggants. Heterocycles containing mercapto groups, for example mercaptobenzthiazoles, mercaptobenzimidazoles, mercaptotetrazoles, mercaptothiadiazoles, mercaptopyrimidines, are particularly suitable, these mercaptoazoles also being able to contain a water-solubilizing group, for example a carboxyl group or sulfo group. Other suitable compounds are published in Research Disclosure No. 17643 (1978), Section VI.

The stabilizers can the silver halide emulsions before, during or after their ripening. Of course, the connections can also be made to others photographic layers that a silver halide layer are assigned.

Mixtures of two or more of the mentioned compounds are used.

The silver halide emulsions are commonly used chemically matured, for example by exposure to Gold compounds or compounds of the divalent Sulfur.

The photographic emulsion layers or other hydrophilic Colloid layers of the one produced according to the invention Photosensitive material can be surface active Contains agents for various purposes, such as coating aids to prevent electrical charging Improvement of the sliding properties, for emulsifying the Dispersion, to prevent adhesion and to improve the photographic characteristics (e.g. acceleration of development, high contrast, sensitization etc.).

1. Rotsensibilisatoren
Dicarbocyanine mit Naphthothiazol oder Benzthiazol als basischen Endgruppen, die in 5- und/oder 6-Stellung durch Halogen, Methyl, Methoxy substituiert sein können sowie 9.11-alkylen-verbrückte, insbesondere 9.11-Neopentylenthiadicarbocyanine mit Alkyl- oder Sulfoalkylsubstituenten am Stickstoff.

2. Grünsensibilisatoren
9-Ethyloxacarbocyanine, die in 5-Stellung durch Chlor oder Phenyl substituiert sind und am Stickstoff der Benzoxazolgruppen Alkyl- oder Sulfoalkylreste, vorzugsweise Sulfoalkylsubstituenten tragen.

3. Blausensibilisatoren
Methincyanine mit Benzoxazol, Benzthiazol, Benzselenazol, Naphthoxazol, Naphthothiazol als basischen Endgruppen, die in 5- und/oder 6-Stellung durch Halogen, Methyl, Methoxy substituiert sein können und mindestens eine, vorzugsweise zwei, Sulfoalkylsubstituenten am Stickstoff tragen. Ferner Apomerocyanine mit einer Rhodaningruppe.

Suitable sensitizing dyes are cyanine dyes, in particular of the following classes:

1. Red sensitizers
Dicarbocyanines with naphthothiazole or benzthiazole as basic end groups, which can be substituted in the 5- and / or 6-position by halogen, methyl, methoxy and 9.11-alkylene-bridged, in particular 9.11-neopentylene thiadicarbocyanines with alkyl or sulfoalkyl substituents on nitrogen.

2. Green sensitizers
9-ethyloxacarbocyanines which are substituted in the 5-position by chlorine or phenyl and carry alkyl or sulfoalkyl radicals, preferably sulfoalkyl substituents, on the nitrogen of the benzoxazole groups.

3. Blue sensitizers
Methine cyanines with benzoxazole, benzthiazole, benzselenazole, naphthoxazole, naphthothiazole as basic end groups, which can be substituted in the 5- and / or 6-position by halogen, methyl, methoxy and carry at least one, preferably two, sulfoalkyl substituents on the nitrogen. Furthermore apomerocyanines with a rhodanine group.

worin

X₁ - X₆

O, NR₁, S, Se, Te, P(R₁), P(R₁)₃, CH₂, CHR₂, C(R₂)₂

R₁

Alkyl, gegebenenfalls substituiertes Sulfoalkyl, Carboxyalkyl, Aryl, insbesondere Phenyl

R₂

Aryl, insbesondere Phenyl, Alkyl, insbesondere mit 1 bis 5 C-Atomen, CN

R₃, R₄, R₅, R₆, R₁₉ R₂₀, R₂₁, R₂₂

Wasserstoff, Halogen, Alkoxy, Aryloxy, Cyan, Hydroxy, Sulfo, Carboxy, Alkoxycarbonyl, Aryloxycarbonyl, Acylaminosulfonyl, Aminosulfonyl, Alkylaminosulfonyl, Dialkylaminosulfonyl, Arylaminosulfonyl, Diarylaminosulfonyl, Aryl, Arylmercapto, Alkylmercapto oder Alkyl oder
   R₃ und R₆ bzw. R₁₉ und R₂₂ zusammen eine π-Bindung
   R₄ und R₅ bzw. R₂₀ und R₂₁ zusammen einen 3 bis 12-gliedrigen Ring, der Heteroatome und Mehrfachbindungen enthalten kann,

R₇, R₈, R₉

Alkyl, gegebenenfalls substituiertes Sulfoalkyl, Carboxyalkyl oder Aryl

R₁₀, R₁₁, R₁₂

Wasserstoff, Halogen, Cyan, Aryl, Aryloxy, Arylmercapto, Alkyl, Alkoxy oder Alkylmercapto

R₁₃, R₁₄, R₁₅, R₁₆ R₁₇, R₁₈, R₂₃, R₂₄ R₂₅, R₂₆

Wasserstoff, Halogen, Alkoxy, Cyan, Hydroxy, Sulfo, Carboxy, Alkoxycarbonyl, Aryloxycarbonyl, Acylaminosulfonyl, Aminosulfonyl, Alkylaminosulfonyl, Arylaminosulfonyl, Diarylaminosulfonyl, Aryl, Aryloxy, Arylmercapto, Alkyl oder Alkylmercapto,

R₄₈

Wasserstoff, Alkyl, Sulfoalkyl, Carboxyalkyl, Acyl oder eine negative Ladung,

R₄₉

-CN, -CON(R₁)₂ oder -SO₂R₁,

Z

die restlichen Glieder eines 3 bis 12-gliedrigen Ringes, der Heteroatome und Doppelbindungen enthalten kann,

M^⊕

ein Kation,

Y^⊖

ein Anion und

n

0 oder 1

bedeuten.Sensitizers for the range from 495 to 530 nm can be representatives of the following classes of substances represented by the formulas I to XI, XXVI and XXVII:

wherein

X ₁ - X ₆

O, NR ₁ , S, Se, Te, P (R ₁ ), P (R ₁ ) ₃ , CH ₂ , CHR ₂ , C (R ₂ ) ₂

R ₁

Alkyl, optionally substituted sulfoalkyl, carboxyalkyl, aryl, especially phenyl

R ₂

Aryl, in particular phenyl, alkyl, in particular with 1 to 5 carbon atoms, CN

R ₃ , R ₄ , R ₅ , R ₆ , R ₁₉ R ₂₀ , R ₂₁ , R ₂₂

Hydrogen, halogen, alkoxy, aryloxy, cyano, hydroxy, sulfo, carboxy, alkoxycarbonyl, aryloxycarbonyl, acylaminosulfonyl, aminosulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, arylaminosulfonyl, diarylaminosulfonyl, aryl, arylmercapto, alkylmercapto or alkyl or
R ₃ and R ₆ or R ₁₉ and R ₂₂ together form a π bond
R ₄ and R ₅ or R ₂₀ and R ₂₁ together form a 3 to 12-membered ring which may contain heteroatoms and multiple bonds,

R ₇ , R ₈ , R ₉

Alkyl, optionally substituted sulfoalkyl, carboxyalkyl or aryl

R ₁₀ , R ₁₁ , R ₁₂

Hydrogen, halogen, cyan, aryl, aryloxy, arylmercapto, alkyl, alkoxy or alkylmercapto

R ₁₃ , R ₁₄ , R ₁₅ , R ₁₆ R ₁₇ , R ₁₈ , R ₂₃ , R ₂₄ R ₂₅ , R ₂₆

Hydrogen, halogen, alkoxy, cyan, hydroxy, sulfo, carboxy, alkoxycarbonyl, aryloxycarbonyl, acylaminosulfonyl, aminosulfonyl, alkylaminosulfonyl, arylaminosulfonyl, diarylaminosulfonyl, aryl, aryloxy, arylmercapto, alkyl or alkylmercapto,

R ₄₈

Hydrogen, alkyl, sulfoalkyl, carboxyalkyl, acyl or a negative charge,

R ₄₉

-CN, -CON (R ₁ ) ₂ or -SO ₂ R ₁ ,

Z.

the remaining members of a 3 to 12-membered ring which may contain heteroatoms and double bonds,

M ^⊕

a cation,

Y ^⊖

an anion and

n

0 or 1

mean.

Aryl and alkyl radicals can be further substituted. Acyl is especially alkylcarbonyl or arylcarbonyl.

Examples of substituents for the sulfoalkyl radicals are Hydroxy and halogen, especially chlorine.

LS-I-1:

X₁, X₂, X₃ = O, X₄ = S, R₃ und R₆ zusammen eine π-Bindung, R₄ und R₅ zusammen -CH=CH-CH=CH-, R₇, R₈ C₂H₅, R₉, R₁₀ CH₃, R₁₁ H; 498;

LS-I-2:

X₁, X₂, X₃ = O, X₄ = S, R₃ und R₆ zusammen eine π-Bindung, R₄ und R₅ zusammen die restlichen Glieder eines 5-Phenylbenzoxazols, R₇ CH₃, R₈ C₂H₅, R₉ (CH₂)₃-SO₃H, R₁₀, R₁₁ H; 498;

LS-I-3:

X₁, X₂, X₃ = O, X₄ = S, R₃ und R₆ zusammen eine π-Bindung, R₄ und R₅ zusammen die restlichen Glieder eines 5-Hydroxybenzoxazols, R₈ CH₃, R₇, R₉ C₂H₅, R₁₀, R₁₁ H; 495 nm;

LS-I-4:

X₁, X₂, X₃ = O, X₄ = S, R₃ und R₆ zusammen eine π-Bindung, R₄ und R₅ zusammen die restlichen Glieder eines 5-Chlorbensoxazols, R₇, R₈ CH₃, R₉ C₂H₅, R₁₀, R₁₁ H; 495;

LS-I-5:

X₁, X₂, X₃ = O, X₄ = S, R₃ und R₆ zusammen eine π-Bindung, R₄, R₅ 2-Furyl, R₇ H, R₈, R₉, CH₃, R₁₀, R₁₁ H; 500;

LS-I-6:

X₁, X₂, X₃ = O, X₄ = S, R₃ und R₆ zusammen eine π-Bindung, R₄, R₅ 2-Furyl, R₈ H, R₇ CH₃, R₉ (CH₂)₃-SO₃H, R₁₀, R₁₁ H; 505;

LS-I-7:

X₁, X₂, X₃ = O, X₄ = S, R₃ und R₆ zusammen eine π-Bindung, R₄, R₅ 2-Furyl, R₇, R₉ CH₃, R₈ C₂H₅, R₁₀, R₁₁ H; 500;

LS-I-8:

X₁, X₂, X₃ = O, X₄ = S, R₃ und R₆ zusammen eine π-Bindung, R₄, R₅ 2-Furyl, R₇, R₈ CH₃, R₉ (CH₂)₃-SO₃H, R₁₀, R₁₁ H; 492;

LS-I-9:

X₁, X₂, X₃ = O, X₄ = S, R₃ und R₆ zusammen eine π-Bindung, R₄, R₅ Phenyl, R₇ CH₃, R₈ C₂H₅, R₉ 2-Chlor-3-sulfopropyl, R₁₀, R₁₁ H; 493;

LS-I-10:

X₁, X₂, X₃ = O, X₄ = S, R₃ und R₆ zusammen eine π-Bindung, R₄, R₅ Phenyl, R₇ CH₃, R₈ C₂H₅, R₉ (CH₂)₃-SO₃H, R₁₀, R₁₁ H; 495;

LS-I-11:

X₁, X₂, X₃ = O, X₄ = S, R₃ und R₆ zusammen eine π-Bindung, R₄, R₅ Phenyl, R₇, R₈ CH₃, R₉ C₂H₅, R₁₀, R₁₁ H; 499;

LS-I-12:

X₁, X₂, X₃ = O, X₄ = S, R₃ und R₆ zusammen eine π-Bindung, R₄, R₅ Phenyl, R₇, R₈ CH₃, R₉ CH₂-COOH, R₁₀, R₁₁ H; 497;

LS-I-13:

X₁, X₂, X₃ = O, X₄ = S, R₃ und R₆ zusammen eine π-Bindung, R₄ und R₅ zusammen die restlichen Glieder eines 5-Chlorbenzoxazols, R₇, R₈ CH₃, R₉ (CH₂)₃SO₃H, R₁₀, R₁₁ H; 495;

LS-II-14:

X₁, X₂ = S, R₃ und R₆ zusammen eine π-Bindung, R₄ und R₅ zusammen -CH=CH-CH=CH-, R₇, R₉ C₂H₅, R₁₀, R₁₁, R₁₉, R₂₀, R₂₁, R₂₂ H, R₁₂ CN, Y^⊖ ClO₄ ^⊖ , n = 1; 500;

LS-II-15:

X₁, X₂ = S, R₃, R₄, R₅, R₆, R₁₀, R₁₁, R₁₂ H, R₁₉ und R₂₂ zusammen eine π-Bindung, R₂₀ N-Morpholinocarbonyl, R₇, R₉, R₂₁ CH₃, Y^⊖ I^⊖, n = 1; 532;

LS-II-16:

X₁ = O, X₂ = S, R₃ und R₆ zusammen eine π-Bindung, R₄ und R₅ zusammen -CH=C(CH₃)-C(CH₃)=CH-, R₇ CH₃, R₉ (CH₂)₃SO₃ ^⊖ , R₁₀, R₁₁, R₁₂, R₁₉, R₂₀, R₂₁, R₂₂ H, n = 0; 497;

LS-II-17:

X₁, X₂ = S, R₃ und R₆ zusammen eine π-Bindung, R₄ 2-Hydroxyisopropyl, R₅, R₇, R₉ CH₃, R₁₀, R₁₁, R₁₂, R₁₉, R₂₀, R₂₁, R₂₂ H, Y^⊖ I^⊖ , n = 1; 505;

LS-II-18:

X₁, X₂ = S, R₁₉ und R₂₂ zusammen eine π-Bindung, R₂₀ OC₂H₅, R₅, R₁₀, R₁₁, R₁₂, R₃, R₄, R₆, R₂₁ H, R₇, R₉ CH₃, Y^⊖ I^⊖ , n = 1; 520;

LS-II-19:

X₁, X₂ = S, R₃ und R₆ zusammen eine π-Bindung, R₄ Phenyl, R₅, R₇, R₉ CH₃, R₁₀, R₁₁, R₁₂, R₁₉, R₂₀, R₂₁, R₂₂ H, Y^⊖ I^⊖ , n = 1; 532;

LS-II-20

X₁ = O, X₂ = S, R₃ und R₆ zusammen eine π-Bindung, R₄ und R₅ zusammen die restlichen Glieder eines 5-Methylbenzoxazols, R₇ CH₃, R₉ CH₂-CH(Cl)-CH₂-SO₃ ^⊖ , R₁₀, R₁₁, R₁₂, R₁₉, R₂₀, R₂₁, R₂₂ H, n = 0; 492;

LS-II-21

X₁, X₂ = S, R₁₉ und R₂₂ zusammen eine π-Bindung, R₃, R₄, R₅, R₆, R₁₀, R₁₁, R₁₂, R₂₀, R₂₁ H, R₇, R₉ CH₃, Y^⊖ I^⊖ , n = 1; 517;

LS-II-22

X₁ = O, X₂ = S, R₃ und R₆ zusammen eine π-Bindung, R₄ und R₅ zusammen die restlichen Glieder eines 5-Phenylbenzoxazols, R₇, R₉ CH₃, R₁₀, R₁₁, R₁₂, R₁₉, R₂₀, R₂₁, R₂₂ H; Y^⊖ CH₃OSO₃ ^⊖ , n = 1; 492;

LS-II-23

X₁, X₂ = S, R₁₉ und R₂₂ zusammen eine π-Bindung, R₃, R₄, R₅, R₆, R₁₀, R₁₁, R₁₂ = M, R₇ R₉, R₂₀, R₂₁ = CH₃, Y^⊖ I^⊖ , n = 1; 518;

LS-II-24

X₁, X₂ = S, R₃ und R₆ zusammen eine π-Bindung, R₄ und R₅ zusammen -CH=CH-CH=CH-, R₇ C₂H₅, R₉ CH₃, R₁₀, R₁₁, R₁₉, R₂₀, R₂₁, R₂₂ H, R₁₂ CN, Y^⊖ ClO₄ ^⊖, n = 1; 500;

LS-II-25

X₁, X₂ = S, R₁₉ und R₂₂ zusammen eine π-Bindung, R₃, R₄, R₅, R₆, R₁₀, R₁₁, R₁₂, R₂₀ H, R₂₁ Phenyl, R₇, R₉ C₂H₅, Y^⊖ ClO₄ ^⊖ , n = 1; 520;

LS-II-26

X₁, X₂ = O, R₃ und R₆ zusammen, sowie R₁₉ und R₂₂ zusammen je eine π-Bindung, R₄, R₁₀, R₁₂, R₂₀ H, R₅, R₂₁ Phenyl, R₁₁ CH₃, R₇ (CH₂)₃SO₃ ^⊖ , R₉ (CH₂)₃SO₃H, n = 0; 515;

LS-II-27

X₁, X₂ = O, R₃ und R₆ zusammen sowie R₁₉ und R₂₂ zusammen je eine π-Bindung, R₄, R₁₀, R₁₂, R₂₀ H, R₅, R₂₁ CH₃, R₁₁ C₂H₅, R₇ (CH₂)₃SO₃ ^⊖, R₉ (CH₂)₃SO₃H, n = 0; 500;

LS-II-28

X₁, X₂ = O, R₃ und R₆ zusammen sowie R₁₉ und R₂₂ zusammen je eine π-Bindung, R₄, R₁₀, R₁₂, R₂₀ H, R₅, R₂₁ CH₃, R₇, R₁₁ C₂H₅, R₉ (CH₂)₃SO₃ ^⊖ , n = 0; 498;

LS-II-29

X₁, X₂ = O, R₃ und R₆ zusammen sowie R₁₉ und R₂₂ zusammen je eine π-Bindung, R₄, R₁₀, R₁₂, R₂₀ H, R₅, R₂₁ Phenyl, R₇, R₁₁ C₂H₅, R₉ (CH₂)₃SO₃ ^⊖ , n = 0; 513;

LS-II-30

X₁, X₂ = O, R₃ und R₆ zusammen sowie R₁₉ und R₂₂ zusammen je eine π-Bindung, R₄, R₁₀, R₁₂, R₂₀ H, R₅, R₂₁ Phenyl, R₇, R₁₁ C₂H₅, R₉ (CH₂)₃SO₃ ^⊖ , n = 0; 513;

LS-II-31

X₁, X₂ = O, R₃ und R₆ zusammen sowie R₁₉ und R₂₂ zusammen je eine π-Bindung, R₄, R₁₀, R₁₂, R₂₀ H, R₅, R₂₁ Phenyl, R₉ (CH₂)₃SO₃ ^⊖ , R₇ (CH₂)₃SO₃H, R₁₁ C₂H₅, n = 0; 515;

LS-II-32

X₁, X₂ = O, R₃ und R₆ zusammen sowie R₁₉ und R₂₂ zusammen je eine π-Bindung, R₄, R₅, R₂₀, R₂₁, R₁₁ CH₃, R₁₀, R₁₂ H, R₉ (CH₂)₃SO₃ ^⊖ , R₇ (CH₂)₃SO₃H, n = 0; 510;

LS-II-33

X₁, X₂ = O, R₃ und R₆ zusammen sowie R₁₉ und R₂₂ zusammen je eine π-Bindung, R₄, R₅, R₂₀, R₂₁ CH₃, R₉ (CH₂)₃SO₃ ^⊖ , R₇ (CH₂)₃SO₃H, R₁₀, R₁₂ H, R₁₁ C₂H₅, n = 0; 510;

LS-II-34

X₁, X₂ = O, R₃ und R₆ zusammen sowie R₁₉ und R₂₂ zusammen je eine π-Bindung, R₄, R₂₀ Ethoxycarbonyl, R₅, R₂₁, R₇, R₉, R₁₁ CH₃, R₁₀, R₁₂ H, Y^⊖ ClO₄ ^⊖ , n = 1; 498;

LS-II-35

X₁, X₂ = O, R₃ und R₆ zusammen sowie R₁₉ und R₂₂ zusammen je eine π-Bindung, R₄, R₂₀ Ethoxycarbonyl, R₅, R₇, R₉, R₂₁ CH₃, R₁₀, R₁₁, R₁₂ H, Y^⊖ ClO₄ ^⊖ , n = 1; 502;

LS-II-36

X₁, X₂ = O, R₃ und R₆ zusammen sowie R₁₉ und R₂₂ zusammen je eine π-Bindung, R₄, R₂₀ Ethoxycarbonyl, R₅, R₂₁ CH₃, R₇ (CH₂)₃SO₃ ^⊖ , R₉ (CH₂)₃SO₃H, R₁₀, R₁₂ H, R₁₁ C₂H₅, n = 0; 500;

LS-II-37

X₁, X₂ = O, R₃ und R₆ zusammen sowie R₁₉ und R₂₂ zusammen je eine π-Bindung, R₄, R₂₀ Ethoxycarbonyl, R₅, R₁₁, R₂₁ CH₃, R₇ (CH₂)₃SO₃ ^⊖, R₉ (CH₂)₃SO₃H, R₁₀, R₁₂ H, n = 0; 500;

LS-II-38

X₁, X₂ = O, R₃ und R₆ zusammen sowie R₁₉ und R₂₂ zusammen je eine π-Bindung, R₄, R₂₀ Ethoxycarbonyl, R₅, R₁₁, R₂₁ CH₃, R₉ (CH₂)₃SO₃ ^⊖, R₇ C₂H₅, R₁₀, R₁₂ H, n = 0; 499;

LS-II-39

X₁, X₂ = O, R₃ und R₆ zusammen sowie R₁₉ und R₂₂ zusammen je eine π-Bindung, R₄, R₂₀ Ethoxycarbonyl, R₅, R₂₁ CH₃, R₉ (CH₂)₃SO₃ ^⊖ , R₇ R₁₁ C₂H₅, R₁₀, R₁₂ H, n = 0; 499;

LS-II-40

X₁, X₂ = O, R₃ und R₆ zusammen sowie R₁₉ und R₂₂ zusammen je eine π-Bindung, R₄, R₅, R₁₁, R₂₀, R₂₁ CH₃, R₉ (CH₂)₃SO₃ ^⊖ , R₇ C₂H₅, R₁₀, R₁₂ H, n = 0; 508;

LS-II-41

X₁, X₂ = O, R₃ und R₆ zusammen sowie R₁₉ und R₂₂ zusammen je eine π-Bindung, R₄, R₅, R₂₀, R₂₁ CH₃, R₉ (CH₂)₃SO₃ ^⊖ , R₇, R₁₁ C₂H₅, R₁₀, R₁₂ H, n = 0; 508;

LS-II-42

X₁ = S, X₂ = O, R₁₉ und R₂₂ zusammen eine π-Bindung, R₂₀ und R₂₁ die restlichen Glieder eines 5-Phenylbenzoxazols, R₉ (CH₂)₃SO₃ ^⊖ , R₇, R₁₁ C₂H₅, R₁₀, R₁₂, R₃, R₄, R₅, R₆ H, n = 0; 502;

LS-II-43

X₁ = S, X₂ = O, R₁₉ und R₂₂ zusammen eine π-Bindung, R₂₀ und R₂₁ die restlichen Glieder eines 5-Chlorbenzoxazols, R₉ (CH₂)₃SO₃ ^⊖ , R₇, R₁₁ C₂H₅, R₁₀, R₁₂, R₃, R₄, R₅, R₆ H, n = 0; 498;

LS-II-44

X₁, X₂ = S, R₁₉ und R₂₂ zusammen eine π-Bindung, R₃, R₄, R₅, R₆, R₁₀, R₁₂, R₂₀ H, R₂₁ Phenyl, R₉ (CH₂)₃SO₃ ^⊖ , R₇ (CH₂)₃SO₃H, R₁₁ C₂H₅, n = 0; 505;

LS-II-45

X₁, X₂ = S, R₁₉ und R₂₂ zusammen eine π-Bindung, R₃, R₄, R₅, R₆ R₁₀, R₁₂, R₂₀ H, R₂₁ Cl, R₉ (CH₂)₃SO₃ ^⊖ , R₇ (CH₂)₃SO₃H, R₁₁ C₂H₅, n = 0; 502;

LS-II-46

X₁, X₂ = S, R₁₉ und R₂₂ zusammen eine π-Bindung, R₂₀, R₂₁ CH₃, R₉ (CH₂)₃SO₃ ^⊖ , R₇ (CH₂)₃SO₃H, R₃, R₄, R₅, R₆ R₁₀, R₁₂ H, R₁₁ C₂H₅, n = 0; 520;

LS-II-47

X₁, X₂ = S, R₁₉ und R₂₁ zusammen eine π-Bindung, R₂₀, R₂₁ CH₃, R₉ (CH₂)₃SO₃ ^⊖ , R₇, R₁₁ C₂H₅, R₃, R₄, R₅, R₆, R₁₀, R₁₂ H, n = 0; 520;

LS-III-48

X₃, X₅ = O, X₄ = S, R₇, R₈, R₉ CH₃, R₁₀, R₁₁, R₁₃, R₁₄, R₁₅, R₁₆ H; 497;

LS-III-49

X₃, X₅ = O, X₄ = S, R₇ (CH₂)₃SO₃H, R₈, R₉ CH₃, R₁₀, R₁₁, R₁₃, R₁₄, R₁₅, R₁₆ H; 500;

LS-III-50

X₃, X₅ = O, X₄ = S, R₇, R₈ (CH₂)₃SO₃H, R₉ CH₃, R₁₀, R₁₁, R₁₃, R₁₄, R₁₅, R₁₆ H; 505;

LS-III-51

X₃, X₅ = O, X₄ = S, R₇, R₈ CH₃, R₉ (CH₂)₃SO₃H, R₁₀, R₁₁, R₁₃, R₁₄, R₁₅, R₁₆ H; 500;

LS-IV-52

X₁, X₃ = S, X₂, X₄ = O, R₃, R₄, R₅, R₆, R₁₀, R₁₁ H, R₇, R₉ C₂H₅; 500;

LS-IV-53

X₁, X₃ = S, X₂, X₄ = O, R₃, R₄, R₅, R₆, R₁₀, R₁₁ H, R₇ C₂H₅, R₉ CH₃; 500;

LS-IV-54

X₁, X₃ = S, X₂, X₄ = O, R₃, R₄, R₅, R₆, R₁₀, R₁₁ H, R₇ C₂H₅, R₉ (CH₂)₃SO₃H; 500;

LS-IV-55

X₁, X₃ = S, X₂, X₄ = O, R₃, R₄, R₅, R₆, R₁₀, R₁₁ H, R₇ (CH₂)₃SO₃H, R₉ C₂H₅; 500;

LS-IV-56

X₁ = CH₂, X₂, X₃ = S, X₄ = O, R₃, R₄, R₅, R₆, R₁₁ H, R₇ C₂H₅, R₉ (CH₂)₂CH(CH₃)SO₃H, R₁₀ CH₃; 523;

LS-IV-57

X₁ = CH₂, X₂, X₃ = S, X₄ = O, R₃, R₄, R₅, R₆, R₁₁ H, R₇, R₁₀ C₂H₅, R₉ (CH₂)₂CH(CH₃)SO₃H; 522;

LS-IV-58

X₁ = CH₂, X₂ = NCH₃, X₃ = S, X₄ = O, R₃, R₄, R₅, R₆, R₁₀, R₁₁ H, R₇ CH₃, R₉ (CH₂)₃SO₃H; 500;

LS-IV-59

X₁ = CH₂, X₂ = NCH₃, X₃ = S, X₄ = O, R₃, R₄, R₅, R₆, R₁₀, R₁₁ H, R₇, R₉ CH₃; 495;

LS-V-60

X₁ = O, R₇ C₂H₅, R₉ (CH₂)₄SO₃ ^⊖ , R₁₀, R₁₃, R₁₄, R₁₆, R₁₇, R₁₈, R₂₃, R₂₅, R₂₆ H, R₁₅ Phenyl, R₂₄ OCH₃, n = 0; 500;

LS-V-61

X₁ = O, R₇, R₉ C₂H₅, R₁₀, R₁₃, R₁₄, R₁₆, R₁₇, R₁₈, R₂₃, R₂₅, R₂₆ H, R₁₅ Phenyl, R₂₄ OCH₃, Y^⊖ I^⊖ , n = 1; 500;

LS-V-62

X₁ = O, R₇ C₂H₅, R₉ (CH₂)₃SO₃ ^⊖ , R₁₀, R₁₃, R₁₄, R₁₆, R₁₇, R₁₈, R₂₃, R₂₅, R₂₆ H, R₁₅ Phenyl, R₂₄ OCH₃, n = 0; 500;

LS-V-63

X₁ = O, R₇ C₂H₅, R₉ (CH₂)₂SO₃ ^⊖ , R₁₀, R₁₃, R₁₄, R₁₆, R₁₇, R₁₈, R₂₃, R₂₅, R₂₆ H, R₁₅ Phenyl, R₂₄ OCH₃, n = 0; 500;

LS-V-64

X₁ = O, R₇ (CH₂)₃SO₃H, R₉ (CH₂)₃SO₃ ^⊖ , R₁₀, R₁₃, R₁₄, R₁₆, R₁₇, R₁₈, R₂₃, R₂₅, R₂₆ H, R₁₅ Phenyl, R₂₄ OCH₃, n = 0; 505;

LS-V-65

X₁ = O, R₇ (CH₂)₃SO₃H, R₉ (CH₂)₂-SO₃ ^⊖ , R₁₀, R₁₃, R₁₄, R₁₆, R₁₇, R₁₈, R₂₃, R₂₅, R₂₆ H, R₁₅ Phenyl, R₂₄ OCH₃, n = 0; 505;

LS-V-66

X₁ = O, R₇ C₂H₅, R₉ (CH₂)₃SO₃ ^⊖ , R₁₀, R₁₃, R₁₄, R₁₆, R₁₇, R₁₈, R₂₃, R₂₅, R₂₆ H, R₁₅ Chlor, R₂₄ OCH₃, n = 0; 500;

LS-V-67

X₁ = O, R₇ (CH₂)₃SO₃H, R₉ (CH₂)₃SO₃ ^⊖ , R₁₀, R₁₃, R₁₄, R₁₆, R₁₇, R₁₈, R₂₃, R₂₅, R₂₆ H, R₁₅ Chlor, R₂₄ OCH₃, n = 0; 503;

LS-V-68

X₁ = S, R₇, R₉ C₂H₅, R₁₀, R₁₃, R₁₄, R₁₆, R₂₃, R₂₄, R₂₅, R₂₆ H, R₁₅ SO₃ ^⊖ , n = 0; 500;

LS-VI-69

X₁ = O, X₃ = S, Z -CH₂-CH₂-CH₂-, R₃ und R₆ zusammen eine π-Bindung, R₄ und R₅ zusammen -CH=CH-CH=CH-, R₉ (CH₂)₃SO₃H, R₁₀ CN, R₁₁, R₁₂, R₁₃, R₁₄ H; 500;

LS-VI-70

X₁ = O, X₃ = S, Z -CH₂-CH₂-CH₂-, R₃ und R₆ zusammen eine π-Bindung, R₄ und R₅ zusammen die restlichen Glieder eines 5-Phenylbenzoxazols, R₉ (CH₂)₃SO₃H, R₁₀ CN, R₁₁, R₁₂, R₁₃, R₁₄ H; 510;

LS-VI-71

X₁ = O, X₃ = S, Z -CH₂-CH₂-CH₂-, R₃ und R₆ zusammen eine π-Bindung, R₄ und R₅ zusammen die restlichen Glieder eines 5-Chlorbenzoxazols, R₉ (CH₂)₃SO₃H, R₁₀ CN, R₁₁, R₁₂, R₁₃, R₁₄ H; 505;

LS-VI-72

X₁ = O, X₃ = S, Z -CH₂-CH₂-CH₂-, R₃ und R₆ zusammen eine π-Bindung, R₄ und R₅ zusammen die restlichen Glieder eines 5-Phenylbenzoxazols, R₉ (CH₂)₂SO₃H, R₁₀ CN, R₁₁, R₁₂, R₁₃, R₁₄ H; 510;

LS-VII-73

X₁, X₂, X₃ = S, X₄ = O, R₃ und R₆ zusammen eine π-Bindung, R₄ C₂H₅OCOCH=CH-, R₅, R₉ CH₃, R₇ HOOC-CH₂; 495;

LS-VII-74

X₁, X₂, X₃ = S, X₄ = O, R₃ und R₆ zusammen eine π-Bindung, R₄ H, R₅ CH₃, R₇ HOOC-CH₂, R₉ (CH₂)₃SO₃H; 495;

LS-VII-75

X₁, X₂, X₃ = S, X₄ = O, R₃ und R₆ zusammen eine π-Bindung, R₄ H, R₅, R₉ CH₃, R₇ (CH₂)₃SO₃H; 495;

LS-VII-76

X₁, X₂, X₃ = S, X₄ = O, R₃ und R₆ zusammen eine π-Bindung, R₄ H, R₅ CH₃, R₇ C₂H₅, R₉ (CH₂)₃SO₃H; 495;

LS-VIII-77

X₁, X₂ = S, X₃ = O, Z -CH₂-CH₂-CH₂, R₇, R₉ C₂H₅, R₈ C₄H₉, R₁₀, R₁₅, R₁₆ H, R₁₃ und R₁₄ zusammen -CH=CH-CH=CH-, Y^⊖ NO₃ ^⊖ , n = 1; 498;

LS-VIII-78

X₁, X₂ = S, X₃ = O, Z -CH₂-CH₂-CH₂, R₇, (CH₂)₃SO₃ ^⊖ , R₈, R₉ C₂H₅, R₁₀, R₁₅, R₁₆ H, R₁₃ und R₁₄ zusammen -CH=CH-CH=CH-, n = 0; 500;

LS-VIII-79

X₁, X₂ = S, X₃ = O, Z -CH₂-CH₂-CH₂, R₇, (CH₂)₃SO₃ ^⊖ , R₈ C₂H₅, R₉ (CH₂)₃SO₃H, R₁₀, R₁₅, R₁₆ H, R₁₃ und R₁₄ zusammen -CH=CH-CH=CH-, n = 0; 503;

LS-IX-80

X₁ = NCH₃, X₂, X₃ = S, X₄, X₅, X₆ = O, R₃ und R₆ zusammen eine π-Bindung, R₄ und R₅ zusammen -CH=CH-CH=CH-, R₇, R₉ CH₃, R₈ C₂H₅; 505;

LS-IX-81

X₁ = NCH₃, X₂, X₆ = S, X₃ = C(CN)₂, X₄, X₅ = O, R₃ und R₆ zusammen eine π-Bindung, R₄ und R₅ zusammen -CH=CH-CH=CH-, R₇, R₈ C₂H₅, R₉ (CH₂)₃SO₃H; 520;

LS-IX-82

X₁ = NCH₃, X₂, X₆ = S, X₃ = C(CN)₂, X₄, X₅ = O, R₃ und R₆ zusammen eine π-Bindung, R₄ und R₅ zusammen -CH=CH-CH=CH-, R₇, R₈ C₂H₅, R₉ CH₃; 520;

LS-IX-83

X₁ = NCH₃, X₂, X₃ = S, X₄, X₅, X₆ = O, R₃ und R₆ zusammen eine π-Bindung, R₄ und R₅ zusammen -CH=CH-CH=CH-, R₇ CH₃, R₈ C₂H₅, R₉ (CH₂)₃SO₃H; 508;

LS-IX-84

X₁, X₂, X₄, X₅ = O, X₃, X₆ = S, R₃ und R₆ zusammen eine π-Bindung, R₄, R₅ 2-Furyl, R₇, R₈ C₂H₅, R₉ CH₃; 500;

LS-IX-85

X₁, X₂, X₄, X₅ = O, X₃, X₆ = S, R₃ und R₆ zusammen eine π-Bindung, R₄, R₅ Phenyl, R₇, R₈ C₂H₅, R₉ (CH₂)₃SO₃H; 498;

LS-IX-86

X₁, X₂, X₄, X₅ = O, X₃, X₆ = S, R₃ und R₆ zusammen eine π-Bindung, R₄, R₅ CH₃, R₇, R₈ C₂H₅, R₉ (CH₂)₃SO₃H; 495;

LS-IX-87

X₁, X₂, X₄, X₅ = O, X₃, X₆ = S, R₃ und R₆ zusammen eine π-Bindung, R₄, R₅ 2-Furyl, R₇, R₈ C₂H₅, R₉ (CH₂)₃SO₃H; 502;

LS-X-88

X₃, X₅ = O, X₄ = S, R₇, R₈, R₉ C₂H₅, R₁₀, R₁₁, R₁₃, R₁₄, R₁₅, R₁₆ H; 498;

LS-X-89

X₃, X₅ = O, X₄ = S, R₇, R₁₀, R₁₁, R₁₃, R₁₄, R₁₅, R₁₆ H, R₈, R₉ CH₃; 490;

LS-X-90

X₃, X₅ = O, X₄ = S, R₇, R₈, R₉ CH₃, R₁₀, R₁₁, R₁₃, R₁₄, R₁₅, R₁₆ H; 500;

LS-X-91

X₃, X₅ = O, X₄ = S, R₇, R₈ CH₃, R₉ (CH₂)₃SO₃H, R₁₀, R₁₁, R₁₃, R₁₄, R₁₅, R₁₆ H; 503;

LS-XI-92

X₁, X₄ = S, X₃, X₅ = O, R₇, R₈ C₂H₅, R₉, R₁₀ CH₃, R₁₁ H, R₁₃ CH₃S; 500;

LS-XI-93

X₁, X₄ = S, X₃, X₅ = O, R₇, R₈, R₉ CH₃, R₁₀, R₁₁ H, R₁₃ CH₃S; 505;

LS-XI-94

X₁, X₄ = S, X₃, X₅ = O, R₇, R₁₃ CH₃, R₈ C₂H₅, R₉ (CH₂)₃SO₃H, R₁₀, R₁₁ H; 495;

LS-XI-95

X₁, X₄ = S, X₃, X₅ = O, R₇, R₈ CH₃, R₉, (CH₂)₃SO₃H, R₁₀, R₁₁ H, R₁₃ Phenyl; 502.

LS-I-134

X₁, X₂, X₃ = O, X₄ = S, R₃ und R₆ zusammen eine π-Bindung, R₄ und R₅ zusammen die restlichen Glieder eines 5-Carboxymethylenoxy-benzoxazols (Pyridiniumsalz), R₇ CH₃, R₈, R₉ C₂H₅, R₁₀, R₁₁ H; 495;

LS-II-135

X₁ = O, X₂ = S, R₃ und R₆ zusammen eine π-Bindung, R₄ und R₅ zusammen die restlichen Glieder eines 5-Carboxymethylen-oxy-benzoxazols, R₇ CH₃, R₉ C₂H₅, R₁₀, R₁₁, R₁₂, R₁₉, R₂₀, R₂₁, R₂₂ H, Y^⊖ I^⊖, n = 1; 500;

LS-II-136

X₁, X₂ = O, R₃ und R₆ zusammen sowie R₁₉ und R₂₂ zusammen je eine π-Bindung, R₄ und R₅ zusammen sowie R₂₀ und R₂₁ zusammen jeweils die restlichen Glieder eine 5-Benzoyloxybenzoxazols, R₇, R₉ C₂H₅, R₁₀, R₁₁, R₁₂ H, Y^⊖ C₂H₅OSO₃ ^⊖, n = 1; 513;

LS-XXVI-137

R₁ C₂H₅, R₄₈ negative Ladung, R₄₉ CN, M⁺K⁺, n = 1; 495;

LS-XXVI-138

R₁ C₂H₅, R₄₈ negative Ladung, R₄₉ -CONH₂, M⁺Na⁺, n = 1; 500;

LS-XXVI-139

R₁ C₂H₅, R₄₈ H, R₄₉ -CONH₂, n = 0; 500;

LS-XXVI-140

R₁ C₂H₅, R₄₈ negative Ladung, R₄₉ -CONHC₂H₅, M⁺ HN⁺(C₂H₅)₃, n = 1; 500;

LS-XXVI-141

R₁ C₂H₅, R₄₈ negative Ladung, R₄₉

M⁺ Na⁺, n = 1; 500;

LS-XXVI-142

R₁ C₂H₅, R₄₈ negative Ladung, R₄₉ CONHCH₂-CH=CH₂, M⁺ Na⁺, n = 1; 500;

LS-XXVI-143

R₁ C₂H₅, R₄₈ negative Ladung, R₄₉ CONHCH₂CH₂OH, M⁺K⁺, n = 1; 500;

LS-XXVI-144

R₁ H, R₄₈ negative Ladung, R₄₉ CONH₂, M⁺K⁺, n = 1; 500;

LS-XXVI-145

R₁ H, R₄₈ negative Ladung, R₄₉ CONHPhenyl, M⁺K⁺, n = 1; 510;

LS-XXVI-146

R₁ Ethyl, R₄₈ negative Ladung, R₄₉ SO₂-Phenyl, M⁺K⁺, n = 1; 495;

LS-XXVII-147

R₁ CH₂COOC₂H₅, R₇, R₈ Phenyl, R₄₈ negative Ladung, M⁺ HN⁺(C₂H₅)₃, n = 1; 500;

LS-XXVII-148

R₁ CH₂CH₂OH; R₇, R₈ Phenyl, R₄₈ negative Ladung, M⁺ HN^⊕ (C₂H₅)₃, n = 1; 500;

LS-XXVII-149

R₁ C₂H₅, R₇, R₈ Phenyl, R₄₈ negative Ladung, M⁺ HN⁺(C₂H₅)₃, n = 1; 500;

LS-XXVII-150

R₁, R₇, R₈ Phenyl, R₄₈ negative Ladung, M⁺ HN⁺(C₂H₅)₃, n = 1; 500.

Suitable examples of formulas I to XI and their sensitization maxima in nm are:

LS-I-1:

X ₁ , X ₂ , X ₃ = O, X ₄ = S, R ₃ and R ₆ together form a π bond, R ₄ and R ₅ together -CH = CH-CH = CH-, R ₇ , R ₈ C ₂ H ₅ , R ₉ , R ₁₀ CH ₃ , R ₁₁ H; 498;

LS-I-2:

X ₁ , X ₂ , X ₃ = O, X ₄ = S, R ₃ and R ₆ together form a π bond, R ₄ and R ₅ together form the remaining members of a 5-phenylbenzoxazole, R ₇ CH ₃ , R ₈ C ₂ H ₅ , R ₉ (CH ₂ ) ₃ -SO ₃ H, R ₁₀ , R ₁₁ H; 498;

LS-I-3:

X ₁ , X ₂ , X ₃ = O, X ₄ = S, R ₃ and R ₆ together form a π bond, R ₄ and R ₅ together form the remaining members of a 5-hydroxybenzoxazole, R ₈ CH ₃ , R ₇ , R ₉ C ₂ H ₅ , R ₁₀ , R ₁₁ H; 495 nm;

LS-I-4:

X ₁ , X ₂ , X ₃ = O, X ₄ = S, R ₃ and R ₆ together form a π bond, R ₄ and R ₅ together form the remaining members of a 5-chlorobensoxazole, R ₇ , R ₈ CH ₃ , R ₉ C ₂ H ₅ , R ₁₀ , R ₁₁ H; 495;

LS-I-5:

X ₁ , X ₂ , X ₃ = O, X ₄ = S, R ₃ and R ₆ together form a π bond, R ₄ , R ₅ 2-furyl, R ₇ H, R ₈ , R ₉ , CH ₃ , R ₁₀ , R ₁₁ H; 500;

LS-I-6:

X ₁ , X ₂ , X ₃ = O, X ₄ = S, R ₃ and R ₆ together form a π bond, R ₄ , R ₅ 2-furyl, R ₈ H, R ₇ CH ₃ , R ₉ (CH ₂ ) ₃ -SO ₃ H, R ₁₀ , R ₁₁ H; 505;

LS-I-7:

X ₁ , X ₂ , X ₃ = O, X ₄ = S, R ₃ and R ₆ together form a π bond, R ₄ , R ₅ 2-furyl, R ₇ , R ₉ CH ₃ , R ₈ C ₂ H ₅ , R ₁₀ , R ₁₁ H; 500;

LS-I-8:

X ₁ , X ₂ , X ₃ = O, X ₄ = S, R ₃ and R ₆ together form a π bond, R ₄ , R ₅ 2-furyl, R ₇ , R ₈ CH ₃ , R ₉ (CH ₂ ) ₃ -SO ₃ H, R ₁₀ , R ₁₁ H; 492;

LS-I-9:

X ₁ , X ₂ , X ₃ = O, X ₄ = S, R ₃ and R ₆ together form a π bond, R ₄ , R ₅ phenyl, R ₇ CH ₃ , R ₈ C ₂ H ₅ , R ₉ 2- Chloro-3-sulfopropyl, R ₁₀ , R ₁₁ H; 493;

LS-I-10:

X ₁ , X ₂ , X ₃ = O, X ₄ = S, R ₃ and R ₆ together form a π bond, R ₄ , R ₅ phenyl, R ₇ CH ₃ , R ₈ C ₂ H ₅ , R ₉ (CH ₂ ) ₃ -SO ₃ H, R ₁₀ , R ₁₁ H; 495;

LS-I-11:

X ₁ , X ₂ , X ₃ = O, X ₄ = S, R ₃ and R ₆ together form a π bond, R ₄ , R ₅ phenyl, R ₇ , R ₈ CH ₃ , R ₉ C ₂ H ₅ , R ₁₀ , R ₁₁ H; 499;

LS-I-12:

X ₁ , X ₂ , X ₃ = O, X ₄ = S, R ₃ and R ₆ together form a π bond, R ₄ , R ₅ phenyl, R ₇ , R ₈ CH ₃ , R ₉ CH ₂ -COOH, R ₁₀ , R ₁₁ H; 497;

LS-I-13:

X ₁ , X ₂ , X ₃ = O, X ₄ = S, R ₃ and R ₆ together form a π bond, R ₄ and R ₅ together form the remaining members of a 5-chlorobenzoxazole, R ₇ , R ₈ CH ₃ , R ₉ (CH ₂ ) ₃ SO ₃ H, R ₁₀ , R ₁₁ H; 495;

LS-II-14:

X ₁ , X ₂ = S, R ₃ and R ₆ together form a π bond, R ₄ and R ₅ together -CH = CH-CH = CH-, R ₇ , R ₉ C ₂ H ₅ , R ₁₀ , R ₁₁ , R ₁₉ , R ₂₀ , R ₂₁ , R ₂₂ H, R ₁₂ CN, Y ^⊖ ClO ₄ ^⊖ , n = 1; 500;

LS-II-15:

X ₁ , X ₂ = S, R ₃ , R ₄ , R ₅ , R ₆ , R ₁₀ , R ₁₁ , R ₁₂ H, R ₁₉ and R ₂₂ together form a π bond, R ₂₀ N-morpholinocarbonyl, R ₇ , R ₉ , R ₂₁ CH ₃ , Y ^⊖ I ^⊖ , n = 1; 532;

LS-II-16:

X ₁ = O, X ₂ = S, R ₃ and R ₆ together form a π bond, R ₄ and R ₅ together -CH = C (CH ₃ ) -C (CH ₃ ) = CH-, R ₇ CH ₃ , R ₉ (CH ₂ ) ₃ SO ₃ ^⊖ , R ₁₀ , R ₁₁ , R ₁₂ , R ₁₉ , R ₂₀ , R ₂₁ , R ₂₂ H, n = 0; 497;

LS-II-17:

X ₁ , X ₂ = S, R ₃ and R ₆ together form a π bond, R ₄ 2-hydroxyisopropyl, R ₅ , R ₇ , R ₉ CH ₃ , R ₁₀ , R ₁₁ , R ₁₂ , R ₁₉ , R ₂₀ , R ₂₁ , R ₂₂ H, Y ^⊖ I ^⊖ , n = 1; 505;

LS-II-18:

X ₁ , X ₂ = S, R ₁₉ and R ₂₂ together form a π bond, R ₂₀ OC ₂ H ₅ , R ₅ , R ₁₀ , R ₁₁ , R ₁₂ , R ₃ , R ₄ , R ₆ , R ₂₁ H , R ₇ , R ₉ CH ₃ , Y ^⊖ I ^⊖ , n = 1; 520;

LS-II-19:

X ₁ , X ₂ = S, R ₃ and R ₆ together form a π bond, R ₄ phenyl, R ₅ , R ₇ , R ₉ CH ₃ , R ₁₀ , R ₁₁ , R ₁₂ , R ₁₉ , R ₂₀ , R ₂₁ , R ₂₂ H, Y ^⊖ I ^⊖ , n = 1; 532;

LS-II-20

X ₁ = O, X ₂ = S, R ₃ and R ₆ together form a π bond, R ₄ and R ₅ together form the remaining members of a 5-methylbenzoxazole, R ₇ CH ₃ , R ₉ CH ₂ -CH (Cl) - CH ₂ -SO ₃ ^⊖ , R ₁₀ , R ₁₁ , R ₁₂ , R ₁₉ , R ₂₀ , R ₂₁ , R ₂₂ H, n = 0; 492;

LS-II-21

X ₁ , X ₂ = S, R ₁₉ and R ₂₂ together form a π bond, R ₃ , R ₄ , R ₅ , R ₆ , R ₁₀ , R ₁₁ , R ₁₂ , R ₂₀ , R ₂₁ H, R ₇ , R ₉ CH ₃ , Y ^⊖ I ^⊖ , n = 1; 517;

LS-II-22

X ₁ = O, X ₂ = S, R ₃ and R ₆ together form a π bond, R ₄ and R ₅ together form the remaining members of a 5-phenylbenzoxazole, R ₇ , R ₉ CH ₃ , R ₁₀ , R ₁₁ , R ₁₂ , R ₁₉ , R ₂₀ , R ₂₁ , R ₂₂ H; Y ^⊖ CH ₃ OSO ₃ ^⊖ , n = 1; 492;

LS-II-23

X ₁ , X ₂ = S, R ₁₉ and R ₂₂ together form a π bond, R ₃ , R ₄ , R ₅ , R ₆ , R ₁₀ , R ₁₁ , R ₁₂ = M, R ₇ R ₉ , R ₂₀ , R ₂₁ = CH ₃ , Y ^⊖ I ^⊖ , n = 1; 518;

LS-II-24

X ₁ , X ₂ = S, R ₃ and R ₆ together form a π bond, R ₄ and R ₅ together -CH = CH-CH = CH-, R ₇ C ₂ H ₅ , R ₉ CH ₃ , R ₁₀ , R ₁₁ , R ₁₉ , R ₂₀ , R ₂₁ , R ₂₂ H, R ₁₂ CN, Y ^⊖ ClO ₄ ^⊖ , n = 1; 500;

LS-II-25

X ₁ , X ₂ = S, R ₁₉ and R ₂₂ together form a π bond, R ₃ , R ₄ , R ₅ , R ₆ , R ₁₀ , R ₁₁ , R ₁₂ , R ₂₀ H, R ₂₁ phenyl, R ₇ , R ₉ C ₂ H ₅ , Y ^⊖ ClO ₄ ^⊖ , n = 1; 520;

LS-II-26

X ₁ , X ₂ = O, R ₃ and R ₆ together, and R ₁₉ and R ₂₂ together each have a π bond, R ₄ , R ₁₀ , R ₁₂ , R ₂₀ H, R ₅ , R ₂₁ phenyl, R ₁₁ CH ₃ , R ₇ (CH ₂ ) ₃ SO ₃ ^⊖ , R ₉ (CH ₂ ) ₃ SO ₃ H, n = 0; 515;

LS-II-27

X ₁ , X ₂ = O, R ₃ and R ₆ together and R ₁₉ and R ₂₂ together each have a π bond, R ₄ , R ₁₀ , R ₁₂ , R ₂₀ H, R ₅ , R ₂₁ CH ₃ , R ₁₁ C ₂ H ₅ , R ₇ (CH ₂ ) ₃ SO ₃ ^⊖ , R ₉ (CH ₂ ) ₃ SO ₃ H, n = 0; 500;

LS-II-28

X ₁ , X ₂ = O, R ₃ and R ₆ together and R ₁₉ and R ₂₂ together each have a π bond, R ₄ , R ₁₀ , R ₁₂ , R ₂₀ H, R ₅ , R ₂₁ CH ₃ , R ₇ , R ₁₁ C ₂ H ₅ , R ₉ (CH ₂ ) ₃ SO ₃ ^⊖ , n = 0; 498;

LS-II-29

X ₁ , X ₂ = O, R ₃ and R ₆ together and R ₁₉ and R ₂₂ together each have a π bond, R ₄ , R ₁₀ , R ₁₂ , R ₂₀ H, R ₅ , R ₂₁ phenyl, R ₇ , R ₁₁ C ₂ H ₅ , R ₉ (CH ₂ ) ₃ SO ₃ ^⊖ , n = 0; 513;

LS-II-30

X ₁ , X ₂ = O, R ₃ and R ₆ together and R ₁₉ and R ₂₂ together each have a π bond, R ₄ , R ₁₀ , R ₁₂ , R ₂₀ H, R ₅ , R ₂₁ phenyl, R ₇ , R ₁₁ C ₂ H ₅ , R ₉ (CH ₂ ) ₃ SO ₃ ^⊖ , n = 0; 513;

LS-II-31

X ₁ , X ₂ = O, R ₃ and R ₆ together and R ₁₉ and R ₂₂ together each have a π bond, R ₄ , R ₁₀ , R ₁₂ , R ₂₀ H, R ₅ , R ₂₁ phenyl, R ₉ ( CH ₂ ) ₃ SO ₃ ^⊖ , R ₇ (CH ₂ ) ₃ SO ₃ H, R ₁₁ C ₂ H ₅ , n = 0; 515;

LS-II-32

X ₁ , X ₂ = O, R ₃ and R ₆ together and R ₁₉ and R ₂₂ together each have a π bond, R ₄ , R ₅ , R ₂₀ , R ₂₁ , R ₁₁ CH ₃ , R ₁₀ , R ₁₂ H , R ₉ (CH ₂ ) ₃ SO ₃ ^⊖ , R ₇ (CH ₂ ) ₃ SO ₃ H, n = 0; 510;

LS-II-33

X ₁ , X ₂ = O, R ₃ and R ₆ together and R ₁₉ and R ₂₂ together each have a π bond, R ₄ , R ₅ , R ₂₀ , R ₂₁ CH ₃ , R ₉ (CH ₂ ) ₃ SO ₃ ^⊖ , R ₇ (CH ₂ ) ₃ SO ₃ H, R ₁₀ , R ₁₂ H, R ₁₁ C ₂ H ₅ , n = 0; 510;

LS-II-34

X ₁ , X ₂ = O, R ₃ and R ₆ together and R ₁₉ and R ₂₂ together each have a π bond, R ₄ , R ₂₀ ethoxycarbonyl, R ₅ , R ₂₁ , R ₇ , R ₉ , R ₁₁ CH ₃ , R ₁₀ , R ₁₂ H, Y ^⊖ ClO ₄ ^⊖ , n = 1; 498;

LS-II-35

X ₁ , X ₂ = O, R ₃ and R ₆ together and R ₁₉ and R ₂₂ together each have a π bond, R ₄ , R ₂₀ ethoxycarbonyl, R ₅ , R ₇ , R ₉ , R ₂₁ CH ₃ , R ₁₀ , R ₁₁ , R ₁₂ H, Y ^⊖ ClO ₄ ^⊖ , n = 1; 502;

LS-II-36

X ₁ , X ₂ = O, R ₃ and R ₆ together and R ₁₉ and R ₂₂ together each have a π bond, R ₄ , R ₂₀ ethoxycarbonyl, R ₅ , R ₂₁ CH ₃ , R ₇ (CH ₂ ) ₃ SO ₃ ^⊖ , R ₉ (CH ₂ ) ₃ SO ₃ H, R ₁₀ , R ₁₂ H, R ₁₁ C ₂ H ₅ , n = 0; 500;

LS-II-37

X ₁ , X ₂ = O, R ₃ and R ₆ together and R ₁₉ and R ₂₂ together each have a π bond, R ₄ , R ₂₀ ethoxycarbonyl, R ₅ , R ₁₁ , R ₂₁ CH ₃ , R ₇ (CH ₂ ) ₃ SO ₃ ^⊖ , R ₉ (CH ₂ ) ₃ SO ₃ H, R ₁₀ , R ₁₂ H, n = 0; 500;

LS-II-38

X ₁ , X ₂ = O, R ₃ and R ₆ together and R ₁₉ and R ₂₂ together each have a π bond, R ₄ , R ₂₀ ethoxycarbonyl, R ₅ , R ₁₁ , R ₂₁ CH ₃ , R ₉ (CH ₂ ) ₃ SO ₃ ^⊖ , R ₇ C ₂ H ₅ , R ₁₀ , R ₁₂ H, n = 0; 499;

LS-II-39

X ₁ , X ₂ = O, R ₃ and R ₆ together and R ₁₉ and R ₂₂ together each have a π bond, R ₄ , R ₂₀ ethoxycarbonyl, R ₅ , R ₂₁ CH ₃ , R ₉ (CH ₂ ) ₃ SO ₃ ^⊖ , R ₇ R ₁₁ C ₂ H ₅ , R ₁₀ , R ₁₂ H, n = 0; 499;

LS-II-40

X ₁ , X ₂ = O, R ₃ and R ₆ together and R ₁₉ and R ₂₂ together each have a π bond, R ₄ , R ₅ , R ₁₁ , R ₂₀ , R ₂₁ CH ₃ , R ₉ (CH ₂ ) ₃ SO ₃ ^⊖ , R ₇ C ₂ H ₅ , R ₁₀ , R ₁₂ H, n = 0; 508;

LS-II-41

X ₁ , X ₂ = O, R ₃ and R ₆ together and R ₁₉ and R ₂₂ together each have a π bond, R ₄ , R ₅ , R ₂₀ , R ₂₁ CH ₃ , R ₉ (CH ₂ ) ₃ SO ₃ ^⊖ , R ₇ , R ₁₁ C ₂ H ₅ , R ₁₀ , R ₁₂ H, n = 0; 508;

LS-II-42

X ₁ = S, X ₂ = O, R ₁₉ and R ₂₂ together form a π bond, R ₂₀ and R ₂₁ the remaining members of a 5-phenylbenzoxazole, R ₉ (CH ₂ ) ₃ SO ₃ ^⊖ , R ₇ , R ₁₁ C ₂ H ₅ , R ₁₀ , R ₁₂ , R ₃ , R ₄ , R ₅ , R ₆ H, n = 0; 502;

LS-II-43

X ₁ = S, X ₂ = O, R ₁₉ and R ₂₂ together form a π bond, R ₂₀ and R ₂₁ the remaining members of a 5-chlorobenzoxazole, R ₉ (CH ₂ ) ₃ SO ₃ ^⊖ , R ₇ , R ₁₁ C ₂ H ₅ , R ₁₀ , R ₁₂ , R ₃ , R ₄ , R ₅ , R ₆ H, n = 0; 498;

LS-II-44

X ₁ , X ₂ = S, R ₁₉ and R ₂₂ together form a π bond, R ₃ , R ₄ , R ₅ , R ₆ , R ₁₀ , R ₁₂ , R ₂₀ H, R ₂₁ phenyl, R ₉ (CH ₂ ) ₃ SO ₃ ^⊖ , R ₇ (CH ₂ ) ₃ SO ₃ H, R ₁₁ C ₂ H ₅ , n = 0; 505;

LS-II-45

X ₁ , X ₂ = S, R ₁₉ and R ₂₂ together form a π bond, R ₃ , R ₄ , R ₅ , R ₆ R ₁₀ , R ₁₂ , R ₂₀ H, R ₂₁ Cl, R ₉ (CH ₂ ) ₃ SO ₃ ^⊖ , R ₇ (CH ₂ ) ₃ SO ₃ H, R ₁₁ C ₂ H ₅ , n = 0; 502;

LS-II-46

X ₁ , X ₂ = S, R ₁₉ and R ₂₂ together form a π bond, R ₂₀ , R ₂₁ CH ₃ , R ₉ (CH ₂ ) ₃ SO ₃ ^⊖ , R ₇ (CH ₂ ) ₃ SO ₃ H, R ₃ , R ₄ , R ₅ , R ₆ R ₁₀ , R ₁₂ H, R ₁₁ C ₂ H ₅ , n = 0; 520;

LS-II-47

X ₁ , X ₂ = S, R ₁₉ and R ₂₁ together form a π bond, R ₂₀ , R ₂₁ CH ₃ , R ₉ (CH ₂ ) ₃ SO ₃ ^⊖ , R ₇ , R ₁₁ C ₂ H ₅ , R ₃ , R ₄ , R ₅ , R ₆ , R ₁₀ , R ₁₂ H, n = 0; 520;

LS-III-48

X ₃ , X ₅ = O, X ₄ = S, R ₇ , R ₈ , R ₉ CH ₃ , R ₁₀ , R ₁₁ , R ₁₃ , R ₁₄ , R ₁₅ , R ₁₆ H; 497;

LS-III-49

X ₃ , X ₅ = O, X ₄ = S, R ₇ (CH ₂ ) ₃ SO ₃ H, R ₈ , R ₉ CH ₃ , R ₁₀ , R ₁₁ , R ₁₃ , R ₁₄ , R ₁₅ , R ₁₆ H ; 500;

LS-III-50

X ₃ , X ₅ = O, X ₄ = S, R ₇ , R ₈ (CH ₂ ) ₃ SO ₃ H, R ₉ CH ₃ , R ₁₀ , R ₁₁ , R ₁₃ , R ₁₄ , R ₁₅ , R ₁₆ H ; 505;

LS-III-51

X ₃ , X ₅ = O, X ₄ = S, R ₇ , R ₈ CH ₃ , R ₉ (CH ₂ ) ₃ SO ₃ H, R ₁₀ , R ₁₁ , R ₁₃ , R ₁₄ , R ₁₅ , R ₁₆ H ; 500;

LS-IV-52

X ₁ , X ₃ = S, X ₂ , X ₄ = O, R ₃ , R ₄ , R ₅ , R ₆ , R ₁₀ , R ₁₁ H, R ₇ , R ₉ C ₂ H ₅ ; 500;

LS-IV-53

X ₁ , X ₃ = S, X ₂ , X ₄ = O, R ₃ , R ₄ , R ₅ , R ₆ , R ₁₀ , R ₁₁ H, R ₇ C ₂ H ₅ , R ₉ CH ₃ ; 500;

LS-IV-54

X ₁ , X ₃ = S, X ₂ , X ₄ = O, R ₃ , R ₄ , R ₅ , R ₆ , R ₁₀ , R ₁₁ H, R ₇ C ₂ H ₅ , R ₉ (CH ₂ ) ₃ SO ₃ H; 500;

LS-IV-55

X ₁ , X ₃ = S, X ₂ , X ₄ = O, R ₃ , R ₄ , R ₅ , R ₆ , R ₁₀ , R ₁₁ H, R ₇ (CH ₂ ) ₃ SO ₃ H, R ₉ C ₂ H ₅ ; 500;

LS-IV-56

X ₁ = CH ₂ , X ₂ , X ₃ = S, X ₄ = O, R ₃ , R ₄ , R ₅ , R ₆ , R ₁₁ H, R ₇ C ₂ H ₅ , R ₉ (CH ₂ ) ₂ CH (CH ₃ ) SO ₃ H, R ₁₀ CH ₃ ; 523;

LS-IV-57

X ₁ = CH ₂ , X ₂ , X ₃ = S, X ₄ = O, R ₃ , R ₄ , R ₅ , R ₆ , R ₁₁ H, R ₇ , R ₁₀ C ₂ H ₅ , R ₉ (CH ₂ ) ₂ CH (CH ₃ ) SO ₃ H; 522;

LS-IV-58

X ₁ = CH ₂ , X ₂ = NCH ₃ , X ₃ = S, X ₄ = O, R ₃ , R ₄ , R ₅ , R ₆ , R ₁₀ , R ₁₁ H, R ₇ CH ₃ , R ₉ (CH ₂ ) ₃ SO ₃ H; 500;

LS-IV-59

X ₁ = CH ₂ , X ₂ = NCH ₃ , X ₃ = S, X ₄ = O, R ₃ , R ₄ , R ₅ , R ₆ , R ₁₀ , R ₁₁ H, R ₇ , R ₉ CH ₃ ; 495;

LS-V-60

X ₁ = O, R ₇ C ₂ H ₅ , R ₉ (CH ₂ ) ₄ SO ₃ ^⊖ , R ₁₀ , R ₁₃ , R ₁₄ , R ₁₆ , R ₁₇ , R ₁₈ , R ₂₃ , R ₂₅ , R ₂₆ H , R ₁₅ phenyl, R ₂₄ OCH ₃ , n = 0; 500;

LS-V-61

X ₁ = O, R ₇ , R ₉ C ₂ H ₅ , R ₁₀ , R ₁₃ , R ₁₄ , R ₁₆ , R ₁₇ , R ₁₈ , R ₂₃ , R ₂₅ , R ₂₆ H, R ₁₅ phenyl, R ₂₄ OCH ₃ , Y ^⊖ I ^⊖ , n = 1; 500;

LS-V-62

X ₁ = O, R ₇ C ₂ H ₅ , R ₉ (CH ₂ ) ₃ SO ₃ ^⊖ , R ₁₀ , R ₁₃ , R ₁₄ , R ₁₆ , R ₁₇ , R ₁₈ , R ₂₃ , R ₂₅ , R ₂₆ H , R ₁₅ phenyl, R ₂₄ OCH ₃ , n = 0; 500;

LS-V-63

X ₁ = O, R ₇ C ₂ H ₅ , R ₉ (CH ₂ ) ₂ SO ₃ ^⊖ , R ₁₀ , R ₁₃ , R ₁₄ , R ₁₆ , R ₁₇ , R ₁₈ , R ₂₃ , R ₂₅ , R ₂₆ H , R ₁₅ phenyl, R ₂₄ OCH ₃ , n = 0; 500;

LS-V-64

X ₁ = O, R ₇ (CH ₂ ) ₃ SO ₃ H, R ₉ (CH ₂ ) ₃ SO ₃ ^⊖ , R ₁₀ , R ₁₃ , R ₁₄ , R ₁₆ , R ₁₇ , R ₁₈ , R ₂₃ , R ₂₅ , R ₂₆ H, R ₁₅ phenyl, R ₂₄ OCH ₃ , n = 0; 505;

LS-V-65

X ₁ = O, R ₇ (CH ₂ ) ₃ SO ₃ H, R ₉ (CH ₂ ) ₂ -SO ₃ ^⊖ , R ₁₀ , R ₁₃ , R ₁₄ , R ₁₆ , R ₁₇ , R ₁₈ , R ₂₃ , R ₂₅ , R ₂₆ H, R ₁₅ phenyl, R ₂₄ OCH ₃ , n = 0; 505;

LS-V-66

X ₁ = O, R ₇ C ₂ H ₅ , R ₉ (CH ₂ ) ₃ SO ₃ ^⊖ , R ₁₀ , R ₁₃ , R ₁₄ , R ₁₆ , R ₁₇ , R ₁₈ , R ₂₃ , R ₂₅ , R ₂₆ H , R ₁₅ chlorine, R ₂₄ OCH ₃ , n = 0; 500;

LS-V-67

X ₁ = O, R ₇ (CH ₂ ) ₃ SO ₃ H, R ₉ (CH ₂ ) ₃ SO ₃ ^⊖ , R ₁₀ , R ₁₃ , R ₁₄ , R ₁₆ , R ₁₇ , R ₁₈ , R ₂₃ , R ₂₅ , R ₂₆ H, R ₁₅ chlorine, R ₂₄ OCH ₃ , n = 0; 503;

LS-V-68

X ₁ = S, R ₇ , R ₉ C ₂ H ₅ , R ₁₀ , R ₁₃ , R ₁₄ , R ₁₆ , R ₂₃ , R ₂₄ , R ₂₅ , R ₂₆ H, R ₁₅ SO ₃ ^⊖ , n = 0; 500;

LS-VI-69

X ₁ = O, X ₃ = S, Z -CH ₂ -CH ₂ -CH ₂ -, R ₃ and R ₆ together form a π bond, R ₄ and R ₅ together -CH = CH-CH = CH-, R ₉ (CH ₂ ) ₃ SO ₃ H, R ₁₀ CN, R ₁₁ , R ₁₂ , R ₁₃ , R ₁₄ H; 500;

LS-VI-70

X ₁ = O, X ₃ = S, Z -CH ₂ -CH ₂ -CH ₂ -, R ₃ and R ₆ together a π bond, R ₄ and R ₅ together the remaining members of a 5-phenylbenzoxazole, R ₉ ( CH ₂ ) ₃ SO ₃ H, R ₁₀ CN, R ₁₁ , R ₁₂ , R ₁₃ , R ₁₄ H; 510;

LS-VI-71

X ₁ = O, X ₃ = S, Z -CH ₂ -CH ₂ -CH ₂ -, R ₃ and R ₆ together a π bond, R ₄ and R ₅ together the remaining members of a 5-chlorobenzoxazole, R ₉ ( CH ₂ ) ₃ SO ₃ H, R ₁₀ CN, R ₁₁ , R ₁₂ , R ₁₃ , R ₁₄ H; 505;

LS-VI-72

X ₁ = O, X ₃ = S, Z -CH ₂ -CH ₂ -CH ₂ -, R ₃ and R ₆ together a π bond, R ₄ and R ₅ together the remaining members of a 5-phenylbenzoxazole, R ₉ ( CH ₂ ) ₂ SO ₃ H, R ₁₀ CN, R ₁₁ , R ₁₂ , R ₁₃ , R ₁₄ H; 510;

LS-VII-73

X ₁ , X ₂ , X ₃ = S, X ₄ = O, R ₃ and R ₆ together form a π bond, R ₄ C ₂ H ₅ OCOCH = CH-, R ₅ , R ₉ CH ₃ , R ₇ HOOC- CH ₂ ; 495;

LS-VII-74

X ₁ , X ₂ , X ₃ = S, X ₄ = O, R ₃ and R ₆ together form a π bond, R ₄ H, R ₅ CH ₃ , R ₇ HOOC-CH ₂ , R ₉ (CH ₂ ) ₃ SO ₃ H; 495;

LS-VII-75

X ₁ , X ₂ , X ₃ = S, X ₄ = O, R ₃ and R ₆ together form a π bond, R ₄ H, R ₅ , R ₉ CH ₃ , R ₇ (CH ₂ ) ₃ SO ₃ H; 495;

LS-VII-76

X ₁ , X ₂ , X ₃ = S, X ₄ = O, R ₃ and R ₆ together form a π bond, R ₄ H, R ₅ CH ₃ , R ₇ C ₂ H ₅ , R ₉ (CH ₂ ) ₃ SO ₃ H; 495;

LS-VIII-77

X ₁ , X ₂ = S, X ₃ = O, Z -CH ₂ -CH ₂ -CH ₂ , R ₇ , R ₉ C ₂ H ₅ , R ₈ C ₄ H ₉ , R ₁₀ , R ₁₅ , R ₁₆ H , R ₁₃ and R ₁₄ together -CH = CH-CH = CH-, Y ^⊖ NO ₃ ^⊖ , n = 1; 498;

LS-VIII-78

X ₁ , X ₂ = S, X ₃ = O, Z -CH ₂ -CH ₂ -CH ₂ , R ₇ , (CH ₂ ) ₃ SO ₃ ^⊖ , R ₈ , R ₉ C ₂ H ₅ , R ₁₀ , R ₁₅ , R ₁₆ H, R ₁₃ and R ₁₄ together -CH = CH-CH = CH-, n = 0; 500;

LS-VIII-79

X ₁ , X ₂ = S, X ₃ = O, Z -CH ₂ -CH ₂ -CH ₂ , R ₇ , (CH ₂ ) ₃ SO ₃ ^⊖ , R ₈ C ₂ H ₅ , R ₉ (CH ₂ ) ₃ SO ₃ H, R ₁₀ , R ₁₅ , R ₁₆ H, R ₁₃ and R ₁₄ together -CH = CH-CH = CH-, n = 0; 503;

LS-IX-80

X ₁ = NCH ₃ , X ₂ , X ₃ = S, X ₄ , X ₅ , X ₆ = O, R ₃ and R ₆ together form a π bond, R ₄ and R ₅ together -CH = CH-CH = CH -, R ₇ , R ₉ CH ₃ , R ₈ C ₂ H ₅ ; 505;

LS-IX-81

X ₁ = NCH ₃ , X ₂ , X ₆ = S, X ₃ = C (CN) ₂ , X ₄ , X ₅ = O, R ₃ and R ₆ together form a π bond, R ₄ and R ₅ together -CH = CH-CH = CH-, R ₇ , R ₈ C ₂ H ₅ , R ₉ (CH ₂ ) ₃ SO ₃ H; 520;

LS-IX-82

X ₁ = NCH ₃ , X ₂ , X ₆ = S, X ₃ = C (CN) ₂ , X ₄ , X ₅ = O, R ₃ and R ₆ together form a π bond, R ₄ and R ₅ together -CH = CH-CH = CH-, R ₇ , R ₈ C ₂ H ₅ , R ₉ CH ₃ ; 520;

LS-IX-83

X ₁ = NCH ₃ , X ₂ , X ₃ = S, X ₄ , X ₅ , X ₆ = O, R ₃ and R ₆ together form a π bond, R ₄ and R ₅ together -CH = CH-CH = CH -, R ₇ CH ₃ , R ₈ C ₂ H ₅ , R ₉ (CH ₂ ) ₃ SO ₃ H; 508;

LS-IX-84

X ₁ , X ₂ , X ₄ , X ₅ = O, X ₃ , X ₆ = S, R ₃ and R ₆ together form a π bond, R ₄ , R ₅ 2-furyl, R ₇ , R ₈ C ₂ H ₅ , R ₉ CH ₃ ; 500;

LS-IX-85

X ₁ , X ₂ , X ₄ , X ₅ = O, X ₃ , X ₆ = S, R ₃ and R ₆ together form a π bond, R ₄ , R ₅ phenyl, R ₇ , R ₈ C ₂ H ₅ , R ₉ (CH ₂ ) ₃ SO ₃ H; 498;

LS-IX-86

X ₁ , X ₂ , X ₄ , X ₅ = O, X ₃ , X ₆ = S, R ₃ and R ₆ together form a π bond, R ₄ , R ₅ CH ₃ , R ₇ , R ₈ C ₂ H ₅ , R ₉ (CH ₂ ) ₃ SO ₃ H; 495;

LS-IX-87

X ₁ , X ₂ , X ₄ , X ₅ = O, X ₃ , X ₆ = S, R ₃ and R ₆ together form a π bond, R ₄ , R ₅ 2-furyl, R ₇ , R ₈ C ₂ H ₅ , R ₉ (CH ₂ ) ₃ SO ₃ H; 502;

LS-X-88

X ₃ , X ₅ = O, X ₄ = S, R ₇ , R ₈ , R ₉ C ₂ H ₅ , R ₁₀ , R ₁₁ , R ₁₃ , R ₁₄ , R ₁₅ , R ₁₆ H; 498;

LS-X-89

X ₃ , X ₅ = O, X ₄ = S, R ₇ , R ₁₀ , R ₁₁ , R ₁₃ , R ₁₄ , R ₁₅ , R ₁₆ H, R ₈ , R ₉ CH ₃ ; 490;

LS-X-90

X ₃ , X ₅ = O, X ₄ = S, R ₇ , R ₈ , R ₉ CH ₃ , R ₁₀ , R ₁₁ , R ₁₃ , R ₁₄ , R ₁₅ , R ₁₆ H; 500;

LS-X-91

X ₃ , X ₅ = O, X ₄ = S, R ₇ , R ₈ CH ₃ , R ₉ (CH ₂ ) ₃ SO ₃ H, R ₁₀ , R ₁₁ , R ₁₃ , R ₁₄ , R ₁₅ , R ₁₆ H ; 503;

LS-XI-92

X ₁ , X ₄ = S, X ₃ , X ₅ = O, R ₇ , R ₈ C ₂ H ₅ , R ₉ , R ₁₀ CH ₃ , R ₁₁ H, R ₁₃ CH ₃ S; 500;

LS-XI-93

X ₁ , X ₄ = S, X ₃ , X ₅ = O, R ₇ , R ₈ , R ₉ CH ₃ , R ₁₀ , R ₁₁ H, R ₁₃ CH ₃ S; 505;

LS-XI-94

X ₁ , X ₄ = S, X ₃ , X ₅ = O, R ₇ , R ₁₃ CH ₃ , R ₈ C ₂ H ₅ , R ₉ (CH ₂ ) ₃ SO ₃ H, R ₁₀ , R ₁₁ H; 495;

LS-XI-95

X ₁ , X ₄ = S, X ₃ , X ₅ = O, R ₇ , R ₈ CH ₃ , R ₉ , (CH ₂ ) ₃ SO ₃ H, R ₁₀ , R ₁₁ H, R ₁₃ phenyl; 502.

LS-I-134

X ₁ , X ₂ , X ₃ = O, X ₄ = S, R ₃ and R ₆ together form a π bond, R ₄ and R ₅ together form the remaining members of a 5-carboxymethyleneoxy-benzoxazole (pyridinium salt), R ₇ CH ₃ , R ₈ , R ₉ C ₂ H ₅ , R ₁₀ , R ₁₁ H; 495;

LS-II-135

X ₁ = O, X ₂ = S, R ₃ and R ₆ together form a π bond, R ₄ and R ₅ together form the remaining members of a 5-carboxymethylene-oxy-benzoxazole, R ₇ CH ₃ , R ₉ C ₂ H ₅ , R ₁₀ , R ₁₁ , R ₁₂ , R ₁₉ , R ₂₀ , R ₂₁ , R ₂₂ H, Y ^⊖ I ^⊖ , n = 1; 500;

LS-II-136

X ₁ , X ₂ = O, R ₃ and R ₆ together and R ₁₉ and R ₂₂ together each have a π bond, R ₄ and R ₅ together and R ₂₀ and R ₂₁ together the remaining members each a 5-benzoyloxybenzoxazole, R ₇ , R ₉ C ₂ H ₅ , R ₁₀ , R ₁₁ , R ₁₂ H, Y ^⊖ C ₂ H ₅ OSO ₃ ^⊖ , n = 1; 513;

LS-XXVI-137

R ₁ C ₂ H ₅ , R ₄₈ negative charge, R ₄₉ CN, M ⁺ K ⁺ , n = 1; 495;

LS-XXVI-138

R ₁ C ₂ H ₅ , R ₄₈ negative charge, R ₄₉ -CONH ₂ , M ⁺ Na ⁺ , n = 1; 500;

LS-XXVI-139

R ₁ C ₂ H ₅ , R ₄₈ H, R ₄₉ -CONH ₂ , n = 0; 500;

LS-XXVI-140

R ₁ C ₂ H ₅ , R ₄₈ negative charge, R ₄₉ -CONHC ₂ H ₅ , M ⁺ HN ⁺ (C ₂ H ₅ ) ₃ , n = 1; 500;

LS-XXVI-141

R ₁ C ₂ H ₅ , R ₄₈ negative charge, R ₄₉

M ⁺ Na ⁺ , n = 1; 500;

LS-XXVI-142

R ₁ C ₂ H ₅ , R ₄₈ negative charge, R ₄₉ CONHCH ₂ -CH = CH ₂ , M ⁺ Na ⁺ , n = 1; 500;

LS-XXVI-143

R ₁ C ₂ H ₅ , R ₄₈ negative charge, R ₄₉ CONHCH ₂ CH ₂ OH, M ⁺ K ⁺ , n = 1; 500;

LS-XXVI-144

R ₁ H, R ₄₈ negative charge, R ₄₉ CONH ₂ , M ⁺ K ⁺ , n = 1; 500;

LS-XXVI-145

R ₁ H, R ₄₈ negative charge, R ₄₉ CONHPhenyl, M ⁺ K ⁺ , n = 1; 510;

LS-XXVI-146

R ₁ ethyl, R ₄₈ negative charge, R ₄₉ SO ₂ phenyl, M ⁺ K ⁺ , n = 1; 495;

LS-XXVII-147

R ₁ CH ₂ COOC ₂ H ₅ , R ₇ , R ₈ phenyl, R ₄₈ negative charge, M ⁺ HN ⁺ (C ₂ H ₅ ) ₃ , n = 1; 500;

LS-XXVII-148

R ₁ CH ₂ CH ₂ OH; R ₇ , R ₈ phenyl, R ₄₈ negative charge, M ⁺ HN ^⊕ (C ₂ H ₅ ) ₃ , n = 1; 500;

LS-XXVII-149

R ₁ C ₂ H ₅ , R ₇ , R ₈ phenyl, R ₄₈ negative charge, M ⁺ HN ⁺ (C ₂ H ₅ ) ₃ , n = 1; 500;

LS-XXVII-150

R ₁ , R ₇ , R ₈ phenyl, R ₄₈ negative charge, M ⁺ HN ⁺ (C ₂ H ₅ ) ₃ , n = 1; 500.

innerhalb der Formel II solche der Formeln XIII und XIV:

innerhalb der Formel III solche der Formel XV

innerhalb der Formel IV solche der Formel XVI

innerhalb der Formel V solche der Formel XVII

innerhalb der Formel X solche der Formel XVIII

innerhalb der Formel XI solche der Formel XIX

Compounds of the formulas I, II, III, IV, V, X and XI are preferred, within the formula I those of the formula XII:

within formula II those of formulas XIII and XIV:

within formula III those of formula XV

within the formula IV those of the formula XVI

within the formula V those of the formula XVII

within formula X those of formula XVIII

within the formula XI those of the formula XIX

X

O, S, Se, NR₁,

R₂₇, R₂₈

H, CH₃, Phenyl, 2-Furyl, Cl, Methoxycarbonyl, Ethoxycarbonyl,

R₂₉, R₃₂, R₃₅, R₃₈, R₃₉, R₄₀, R₄₂, R₄₃, R₄₅, R₄₇

Methyl, Ethyl, gegebenenfalls substituiertes Sulfoalkyl, Carboxyalkyl,

R₃₀, R₃₁

Wasserstoff oder R₂₉,

R₃₃

Wasserstoff, Methyl, Ethyl,

R₃₄

H, CN,

R₃₆, R₃₇

H, CH₃, C₂H₅, Phenyl, Ethoxy, Morpholinocarbonyl, 1-Hydroxyisopropyl, Cl, Methoxycarbonyl, Ethoxycarbonyl,

R₄₁

H, Cl, CH₃, OH, OCH₃, Phenyl,

R₄₄

H, OCH₃,

R₄₆

H, CH₃, SCH₃, Cl, Phenyl,

Sensibilisatoren für den Absorptionsbereich 580 bis 650 nm können Vertreter folgender durch die Formeln XX und XXII repräsentierter Farbstoffklassen sein;

worin

R₁, R₂, R₃, R₄, R₁₀, R₁₁

Wasserstoff, Halogen, Alkoxy, Aryloxy, Cyan, Hydroxy, Sulfo, Carboxy, Alkoxycarbonyl, Aryloxycarbonyl, Acylaminosulfonyl, Aminosulfonyl, Alkylaminosulfonyl, Dialkylaminosulfonyl, Arylaminosulfonyl, Diarylaminosulfonyl, Aryl, Arylmercapto, Alkylmercapto oder Alkyl oder

R₁ und R₂

zusammen, bzw. R₂ und R₃, bzw. R₃ und R₄ zusammen, bzw. R₁₀ und R₁₁ zusammen einen aromatischen oder heteroaromatischen 3 bis 12-gliedrigen Ring, insbesondere einen anellierten Benzo- oder Naphthoring,

R₅, R₈

Aryl, Alkyl, gegebenenfalls substituiertes Sulfoalkyl, Carboxyalkyl,

R₆, R₇, R₉

Wasserstoff, Halogen, Cyan, Aryl, Arylmercapto, Aryloxy, Alkyl, Alkylmercapto oder Alkoxy,

X₁, X₂, X₃, X₄

O, NR, S, Se, Te, PR, PR₃, CH₂, CH-Alkyl, C(Alkyl)₂, CH-Aryl, C(Aryl)₂,

Y^⊖

ein Anion und

n

0 oder 1 bedeuten.

Bevorzugte Verbindungen der Formeln XX bis XXII entsprechen den Formeln XXIII, XXIV und XXV:

worin

R₁₂, R₁₃, R₁₈

H oder CH₃,

R₁₄, R₁₅

H, CH₃, Cl oder Phenyl,

R₁₆, R₁₇, R₁₉, R₂₀

H, CH₃, Cl, Phenyl oder

R₁₆

zusammen mit R₁₇ bzw. R₁₉ zusammen mit

R₂₀

die restlichen Glieder eines gegebenenfalls substituierten aromatischen oder heteroaromatischen Ringes bedeuten

und R₅, R₈, X₁ und X₂ die oben genannte Bedeutung haben.The substituents have the following meanings:

X

O, S, Se, NR ₁ ,

R ₂₇ , R ₂₈

H, CH ₃ , phenyl, 2-furyl, Cl, methoxycarbonyl, ethoxycarbonyl,

R ₂₉ , R ₃₂ , R ₃₅ , R ₃₈ , R ₃₉ , R ₄₀ , R ₄₂ , R ₄₃ , R ₄₅ , R ₄₇

Methyl, ethyl, optionally substituted sulfoalkyl, carboxyalkyl,

R ₃₀ , R ₃₁

Hydrogen or R ₂₉ ,

R ₃₃

Hydrogen, methyl, ethyl,

R ₃₄

H, CN,

R ₃₆ , R ₃₇

H, CH ₃ , C ₂ H ₅ , phenyl, ethoxy, morpholinocarbonyl, 1-hydroxyisopropyl, Cl, methoxycarbonyl, ethoxycarbonyl,

R ₄₁

H, Cl, CH ₃ , OH, OCH ₃ , phenyl,

R ₄₄

H, OCH ₃ ,

R ₄₆

H, CH ₃ , SCH ₃ , Cl, phenyl,

Sensitizers for the absorption range 580 to 650 nm can be representatives of the following classes of dyes represented by formulas XX and XXII;

wherein

R ₁ , R ₂ , R ₃ , R ₄ , R ₁₀ , R ₁₁

Hydrogen, halogen, alkoxy, aryloxy, cyano, hydroxy, sulfo, carboxy, alkoxycarbonyl, aryloxycarbonyl, acylaminosulfonyl, aminosulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, arylaminosulfonyl, diarylaminosulfonyl, aryl, arylmercapto, alkylmercapto or alkyl or

R ₁ and R ₂

together, or R ₂ and R ₃ , or R ₃ and R ₄ together, or R ₁₀ and R ₁₁ together an aromatic or heteroaromatic 3 to 12-membered ring, in particular a fused benzo or naphtho ring,

R ₅ , R ₈

Aryl, alkyl, optionally substituted sulfoalkyl, carboxyalkyl,

R ₆ , R ₇ , R ₉

Hydrogen, halogen, cyan, aryl, arylmercapto, aryloxy, alkyl, alkylmercapto or alkoxy,

X ₁ , X ₂ , X ₃ , X ₄

O, NR, S, Se, Te, PR, PR ₃ , CH ₂ , CH-alkyl, C (alkyl) ₂ , CH-aryl, C (aryl) ₂ ,

Y ^⊖

an anion and

n

0 or 1 mean.

Preferred compounds of the formulas XX to XXII correspond to the formulas XXIII, XXIV and XXV:

wherein

R ₁₂ , R ₁₃ , R ₁₈

H or CH ₃ ,

R ₁₄ , R ₁₅

H, CH ₃ , Cl or phenyl,

R ₁₆ , R ₁₇ , R ₁₉ , R ₂₀

H, CH ₃ , Cl, phenyl or

R ₁₆

together with R ₁₇ or R ₁₉ together with

R ₂₀

the remaining members of an optionally substituted aromatic or heteroaromatic ring

and R ₅ , R ₈ , X ₁ and X _{2 have} the meaning given above.

LS-XX-96

X₁, X₂, X₃ = S, X₄ = O, R₁, R₂, R₃, R₄, R₇ H, R₅, R₆ CH₃, R₈ C₂H₅; 595;

LS-XX-97

X₁, X₂, X₃ = S, X₄ = O, R₁, R₂, R₃, R₄, R₆, R₇ H, R₅ CH₃, R₈ C₂H₅; 590;

LS-XX-98

X₁, X₂, X₃ = S, X₄ = O, R₁, R₂, R₃, R₄, R₇ H, R₅, R₈ C₂H₅, R₆ CH₃; 600;

LS-XX-99

X₁, X₂, X₃ = S, X₄ = O, R₁, R₂, R₃, R₄, R₆, R₇ H, R₅ (CH₂)₃SO₃H, R₈ C₂H₅; 600;

LS-XX-100

X₁, X₂, X₃ = S, X₄ = O, R₁, R₂, R₃, R4, R₇ H, R₅, R₆, R₈ C₂H₅; 600;

LS-XXI-101

X₁, X₂ = S, R₁, R₂, R₁₀, R₁₁ Phenyl, R₅, R₇, R₈ C₂H₅, R₆, R₉ H, Y^⊖ I^⊖ , n = 1; 582;

LS-XXI-102

X₁, X₂ = S, R₁ zusammen mit R₂ sowie R₁₀ zusammen mit R₁₁ jeweils -CH=C(CH₃)-C(CH₃)=CH-, R₅, R₈ (CH₂)₂COOH, R₆, R₇, R₉ H, Y^⊖ I^⊖ , n = 1; 600;

LS-XXI-103

X₁, X₂ = S, R₁ zusammen mit R₂ sowie R₁₀ zusammen mit R₁₁ jeweils -CH=C(CH₃)-C(CH₃)=CH-, R₅ CH₂COO(CH₂)₄SO₃ ^⊖ , R₈ CH₂COO(CH₂)₄SO₃H, R₆, R₇, R₉ H, n = 0; 600;

LS-XXI-104

X₁, X₂ = S, R₁ zusammen mit R₂

R₁₀ zusammen mit R₁₁ die restlichen Glieder eines 6-Methylthiazols, R₅, R₇ C₂H₅, R₆, R₉ H, R₈ (CH₂)₃SO₃ ^⊖ , n = 0; 597;

LS-XXI-105

X₁, X₂ = S, R₁ zusammen mit R₂ sowie R₁₀ zusammen mit R₁₁ jeweils

R₅, R₇ C₂H₅, R₆, R₉ H, R₈ (CH₂)₃SO₃ ^⊖ , n = 0; 620;

LS-XXI-106

X₁, X₂ = S, R₁ zusammen mit R₂

R₁₀ zusammen mit R₁₁ -CH=C(CH₃)-C(CH₃)=CH-, R₅ (CH₂)₄SO₃ ^⊖ , R₆, R₉ H, R₇, R₈ C₂H₅, n = 0; 600;

LS-XXI-107

X₁, X₂ = S, R₁ zusammen mit R₂ die restlichen Glieder eines 5-Methylthiazols, R₁₀ zusammen mit R₁₁ die restlichen Glieder eines 5-Methoxythiazols, R₅ C₂H₅, R₆, R₉ H, R₇ CH₂-CH₂-Phenyl, R₈ (CH₂)₃SO₃ ^⊖, n = 0; 593;

LS-XXI-108

X₁, X₂ = S, R₁ zusammen mit R₂ sowie R₁₀ zusammen mit R₁₁ -CH=CH-CH=CH-, R₅, R₈ C₂H₅, R₆, R₉ H, R₇ CH₃, Y^⊖ Br^⊖ , n = 1; 618;

LS-XXI-109

X₁, X₂ = S, R₁ zusammen mit R₂ sowie R₁₀ zusammen mit R₁₁ -CH=CH-CH=CH-, R₅, R₈ C₂H₅, R₆, R₉ CH₃, R₇ H, Y^⊖ I^⊖ , n = 1; 590;

LS-XXI-110

X₁, X₂ = S, R₁ zusammen mit R₂

R₁₀ zusammen mit R₁₁ die restlichen Glieder eines an der OH-Gruppe durch

substituierten 5-Hydroxybenzthiazols, R₅ (CH₂)₃SO₃ ^⊖ , R₇, R₈ CH₃, R₆, R₉ H, n = 0; 600;

LS-XXI-111

X₁, X₂ = S, R₁ zusammen mit R₂ sowie R₁₀ zusammen mit R₁₁ -CH=CH-CH=CH-, R₅, R₈ (CH₂)₂COOH, R₆, R₇, R₉ H, Y^⊖ I^⊖ , n = 1; 600;

LS-XXI-112

X₁, X₂ = S, R₁ zusammen mit R₂ sowie R₁₀ zusammen mit R₁₁ -CH=CH-CH=CH-, R₅ C₂H₅, R₆, R₉ H, R₇ CH₃, R₈ (CH₂)₄SO₃ ^⊖ , n = 0; 620;

LS-XXI-113

X₁ = S, X₂ = Se, R₁ zusammen mit R₂ -CH=CH-CH=CH-, R₁₀ zusammen mit R₁₁ die restlichen Glieder eines 5-Methoxyselenazols, R₅, R₇ CH₃, R₆, R₉ H, R₈ C₂H₅, Y^⊖ ClO₄ ^⊖ , n = 1; 590;

LS-XXI-114

X₁, X₂ = S, R₁ zusammen mit R₂ sowie R₁₀ zusammen mit R₁₁ -CH=CH-CH=CH-, R₅, R₈ C₂H₅, R₆, R₇, R₉ H, Y^⊖ C₂H₅OSO₃ ^⊖ , n = 1; 585;

LS-XXI-115

X₁, X₂ = S, R₁ zusammen mit R₂ sowie R₁₀ zusammen mit R₁₁ -CH=CH-CH=CH-, R₅, R₈ (CH₂)₃COOH, R₆, R₇, R₉ H, Y^⊖ I^⊖ , n = 1; 588;

LS-XXI-116

X₁, X₂ = S, R₁ zusammen mit R₂ sowie R₁₀ zusammen mit R₁₁ -CH=CH-CH=CH-, R₅, R₈ CH₃, R₆, R₉ H, R₇ C₂H₅, Y^⊖ Cl^⊖ , n = 1; 605;

LS-XXI-117

X₁, X₂ = S, R₁ zusammen mit R₂ -CH=CH-CH=CH-, R₁₀ zusammen mit R₁₁

R₅ (CH₂)₂SO₂(CH₂)₂SO₃ ^⊖, R₆, R₉ H, R₇, R₈ C₂H₅, n = 0; 598;

LS-XXI-118

X₁, X₂ = S, R₁ zusammen mit R₂ sowie R₁₀ zusammen mit R₁₁ jeweils -CH=CH-CH=CH-, R₅ (CH₂)₂SO₂(CH₂)₂SO₃ ^⊖ , R₆, R₇, R₉ H, R₈ (CH₂)₂SO₂(CH₂)₂SO₃H, n = 0; 595;

LS-XXI-119

X₁, X₂ = S, R₁ zusammen mit R₂ sowie R₁₀ zusammen mit R₁₁ jeweils die restlichen Glieder eines 5-Methylbenzthiazols, R₅, R₈ C₂H₅, R₆, R₇, R₉ H, Y^⊖ I^⊖ , n = 1; 592;

LS-XXI-120

X₁, X₂ = S, R₁ zusammen mit R₂ sowie R₁₀ zusammen mit R₁₁ jeweils -CH=CH-CH=CH-, R₅ C₂H₅, R₆, R₉ H, R₇ CH₃, R₈ CH₂-CH(OH)-CH₂-SO₃ ^⊖ , n = 0; 580;

LS-XXI-121

X₁, X₂ = S, R₁ zusammen mit R₂ sowie R₁₀ zusammen mit R₁₁ jeweils die restlichen Glieder eines 5-Chlorbenzthiazols, R₅ (CH ₂)₃SO₃ ^⊖ , R₆, R₉ H, R₇ C₂H₅, R₈ (CH₂)₃SO₃H, n = 0; 650;

LS-XXI-122

X₁, X₂ = S, R₁ zusammen mit R₂

R₁₀ zusammen mit R₁₁ die restlichen Glieder eines an der OH-Gruppe durch

substituierten 5-Hydroxybenzthiazols, R₅ (CH₂)₃SO₃ ^⊖ , R₆, R₉ H, R₇, R₈ CH₃, n = 0; 600;

LS-XXI-123

X₁, X₂=S, R₁ zusammen mit R₂

R₁₀ zusammen mit R₁₁ die restlichen Glieder eines an der OH-Gruppe durch

substituierten 5-Hydroxybenzthiazols, R₅ (CH₂)₃SO₃ ^⊖ , R₆, R₉ H, R₈ CH₃, R₇ C₂H₅, n = 0; 640;

LS-XXI-124

X₁, X₂ = S, R₁ zusammen mit R₂ sowie R₁₀ zusammen mit R₁₁ jeweils die restlichen Glieder eines 6-Phenoxybenzthiazols, R₅, R₈ CH₃, R₆, R₉ H, R₇ C₂H₅, Y^⊖ ClO₄ ^⊖, n = 1; 585;

LS-XXI-125

X₁ = Se, X₂ = S, R₁ zusammen mit R₂

R₁₀ zusammen mit R₁₁ die restlichen Glieder eine 5-Hydroxybenzthiazols, R₅ (CH₂)₃SO₃ ^⊖ , R₆, R₉ H, R₇ C₂H₅, R₈ CH₃, n = 0; 600;

LS-XXI-126

X₁ = O, X₂ = Se, R₁ zusammen mit R₂

R₁₀ zusammen mit R₁₁ die restlichen Glieder eines 5-Methyl-6-methoxybenzselenazols, R₅ (CH₂)₃SO₃ ^⊖ , R₆, R₉ H, R₇, R₈ C₂H₅, n = 0; 620;

LS-XXI-127

X₁ = O, X₂ = S, R₁ zusammen mit R₂

R₁₀ zusammen mit R₁₁ die restlichen Glieder eines 5-Chlorbenzthiazols, R₅ (CH₂)₃SO₃ ^⊖ , R₆, R₉ H, R₇ C₂H₅, R₈ (CH₂)₃SO₃H, n = 0; 610;

LS-XXI-128

X₁ = O, X₂ = S, R₁ zusammen mit R₂

R₁₀ zusammen mit R₁₁ die restlichen Glieder eines 5-Chlorbenzthiazols, R₅ (CH₂)₃SO₃ ^⊖ , R₆, R₉ H, R₇ C₂H₅, R₈ (CH₂)₄SO₃H, n = 0; 610;

LS-XXI-129

X₁, X₂ = Se, R₁ zusammen mit R₂ sowie R₁₀ zusammen mit R₁₁ -CH=CH-CH=CH-, R₅, R₈ C₂H₅, R₆, R₉ H, R₇ CH₃, Y^⊖ClO₄ ^⊖ , n = 1; 635;

LS-XXI-130

X₁ = S, X₂ = N-C₂H₅, R₁ zusammen mit R₂

R₁₀ zusammen mit R₁₁

R₅ (CH₂)₃SO₃ ^⊖ , R₆, R₇, R₉ H, R₈ (CH₂)₂CH(CH₃)SO₃H, n = 0; 620;

LS-XXI-131

X₁ = O, X₂ = Se, R₁ zusammen mit R₂ die restlichen Glieder eines 5-Methylbenzoxazols, R₁₀ zusammen mit R₁₁ die restlichen Glieder eines 5-Methyl-6-methoxybenzselenazols, R₅ (CH₂)₃SO₃ ^⊖ , R₆, R₉ H, R₇, R₈ C₂H₅, n = 0; 620;

LS-XXI-132

X₁ = S, X₂ = Se, R₁ zusammen mit R₂ sowie R₁₀ zusammen mit R₁₁ jeweils -CH=CH-CH=CH-, R₅ (CH₂)₂SO₂(CH₂)₂SO₃ ^⊖, R₆, R₉ H, R₇ CH₃, R₈ C₂H₅, n = 0; 590;

LS-XXII-133

X₂ = C(CH₃)₂, R₁ zusammen mit R₂ sowie R₁₀ zusammen mit R₁₁ jeweils -CH=CH-CH=CH-, R₅ -(CH₂)₄-SO₃ ^⊖ , R₆, R₇, R₉ H, R₈ CH₃, n = 0; 580.

Suitable examples of the formulas XX to XXII and their sensitization maxima in nm are:

LS-XX-96

X ₁ , X ₂ , X ₃ = S, X ₄ = O, R ₁ , R ₂ , R ₃ , R ₄ , R ₇ H, R ₅ , R ₆ CH ₃ , R ₈ C ₂ H ₅ ; 595;

LS-XX-97

X ₁ , X ₂ , X ₃ = S, X ₄ = O, R ₁ , R ₂ , R ₃ , R ₄ , R ₆ , R ₇ H, R ₅ CH ₃ , R ₈ C ₂ H ₅ ; 590;

LS-XX-98

X ₁ , X ₂ , X ₃ = S, X ₄ = O, R ₁ , R ₂ , R ₃ , R ₄ , R ₇ H, R ₅ , R ₈ C ₂ H ₅ , R ₆ CH ₃ ; 600;

LS-XX-99

X ₁ , X ₂ , X ₃ = S, X ₄ = O, R ₁ , R ₂ , R ₃ , R ₄ , R ₆ , R ₇ H, R ₅ (CH ₂ ) ₃ SO ₃ H, R ₈ C ₂ H ₅ ; 600;

LS-XX-100

X ₁ , X ₂ , X ₃ = S, X ₄ = O, R ₁ , R ₂ , R ₃ , R4, R ₇ H, R ₅ , R ₆ , R ₈ C ₂ H ₅ ; 600;

LS-XXI-101

X ₁ , X ₂ = S, R ₁ , R ₂ , R ₁₀ , R ₁₁ phenyl, R ₅ , R ₇ , R ₈ C ₂ H ₅ , R ₆ , R ₉ H, Y ^⊖ I ^⊖ , n = 1; 582;

LS-XXI-102

X ₁ , X ₂ = S, R ₁ together with R ₂ and R ₁₀ together with R ₁₁ each -CH = C (CH ₃ ) -C (CH ₃ ) = CH-, R ₅ , R ₈ (CH ₂ ) ₂ COOH, R ₆ , R ₇ , R ₉ H, Y ^⊖ I ^⊖ , n = 1; 600;

LS-XXI-103

X ₁ , X ₂ = S, R ₁ together with R ₂ and R ₁₀ together with R ₁₁ each -CH = C (CH ₃ ) -C (CH ₃ ) = CH-, R ₅ CH ₂ COO (CH ₂ ) ₄ SO ₃ ^⊖ , R ₈ CH ₂ COO (CH ₂ ) ₄ SO ₃ H, R ₆ , R ₇ , R ₉ H, n = 0; 600;

LS-XXI-104

X ₁ , X ₂ = S, R ₁ together with R ₂

R ₁₀ together with R ₁₁ the remaining members of a 6-methylthiazole, R ₅ , R ₇ C ₂ H ₅ , R ₆ , R ₉ H, R ₈ (CH ₂ ) ₃ SO ₃ ^⊖ , n = 0; 597;

LS-XXI-105

X ₁ , X ₂ = S, R ₁ together with R ₂ and R ₁₀ together with R ₁₁ each

R ₅ , R ₇ C ₂ H ₅ , R ₆ , R ₉ H, R ₈ (CH ₂ ) ₃ SO ₃ ^⊖ , n = 0; 620;

LS-XXI-106

X ₁ , X ₂ = S, R ₁ together with R ₂

R ₁₀ together with R ₁₁ -CH = C (CH ₃ ) -C (CH ₃ ) = CH-, R ₅ (CH ₂ ) ₄ SO ₃ ^⊖ , R ₆ , R ₉ H, R ₇ , R ₈ C ₂ H ₅ , n = 0; 600;

LS-XXI-107

X ₁ , X ₂ = S, R ₁ together with R ₂ the remaining members of a 5-methylthiazole, R ₁₀ together with R ₁₁ the remaining members of a 5-methoxythiazole, R ₅ C ₂ H ₅ , R ₆ , R ₉ H, R ₇ CH ₂ -CH ₂ -phenyl, R ₈ (CH ₂ ) ₃ SO ₃ ^⊖ , n = 0; 593;

LS-XXI-108

X ₁ , X ₂ = S, R ₁ together with R ₂ and R ₁₀ together with R ₁₁ -CH = CH-CH = CH-, R ₅ , R ₈ C ₂ H ₅ , R ₆ , R ₉ H, R ₇ CH ₃ , Y ^⊖ Br ^⊖ , n = 1; 618;

LS-XXI-109

X ₁ , X ₂ = S, R ₁ together with R ₂ and R ₁₀ together with R ₁₁ -CH = CH-CH = CH-, R ₅ , R ₈ C ₂ H ₅ , R ₆ , R ₉ CH ₃ , R ₇ H, Y ^⊖ I ^⊖ , n = 1; 590;

LS-XXI-110

X ₁ , X ₂ = S, R ₁ together with R ₂

R ₁₀ together with R ₁₁ through the remaining members on the OH group

substituted 5-hydroxybenzthiazole, R ₅ (CH ₂ ) ₃ SO ₃ ^⊖ , R ₇ , R ₈ CH ₃ , R ₆ , R ₉ H, n = 0; 600;

LS-XXI-111

X ₁ , X ₂ = S, R ₁ together with R ₂ and R ₁₀ together with R ₁₁ -CH = CH-CH = CH-, R ₅ , R ₈ (CH ₂ ) ₂ COOH, R ₆ , R ₇ , R ₉ H, Y ^⊖ I ^⊖ , n = 1; 600;

LS-XXI-112

X ₁ , X ₂ = S, R ₁ together with R ₂ and R ₁₀ together with R ₁₁ -CH = CH-CH = CH-, R ₅ C ₂ H ₅ , R ₆ , R ₉ H, R ₇ CH ₃ , R ₈ (CH ₂ ) ₄ SO ₃ ^⊖ , n = 0; 620;

LS-XXI-113

X ₁ = S, X ₂ = Se, R ₁ together with R ₂ -CH = CH-CH = CH-, R ₁₀ together with R ₁₁ the remaining members of a 5-methoxyselenazole, R ₅ , R ₇ CH ₃ , R ₆ , R ₉ H, R ₈ C ₂ H ₅ , Y ^⊖ ClO ₄ ^⊖ , n = 1; 590;

LS-XXI-114

X ₁ , X ₂ = S, R ₁ together with R ₂ and R ₁₀ together with R ₁₁ -CH = CH-CH = CH-, R ₅ , R ₈ C ₂ H ₅ , R ₆ , R ₇ , R ₉ H , Y ^⊖ C ₂ H ₅ OSO ₃ ^⊖ , n = 1; 585;

LS-XXI-115

X ₁ , X ₂ = S, R ₁ together with R ₂ and R ₁₀ together with R ₁₁ -CH = CH-CH = CH-, R ₅ , R ₈ (CH ₂ ) ₃ COOH, R ₆ , R ₇ , R ₉ H, Y ^⊖ I ^⊖ , n = 1; 588;

LS-XXI-116

X ₁ , X ₂ = S, R ₁ together with R ₂ and R ₁₀ together with R ₁₁ -CH = CH-CH = CH-, R ₅ , R ₈ CH ₃ , R ₆ , R ₉ H, R ₇ C ₂ H ₅ , Y ^⊖ Cl ^⊖ , n = 1; 605;

LS-XXI-117

X ₁ , X ₂ = S, R ₁ together with R ₂ -CH = CH-CH = CH-, R ₁₀ together with R ₁₁

R ₅ (CH ₂ ) ₂ SO ₂ (CH ₂ ) ₂ SO ₃ ^⊖ , R ₆ , R ₉ H, R ₇ , R ₈ C ₂ H ₅ , n = 0; 598;

LS-XXI-118

X ₁ , X ₂ = S, R ₁ together with R ₂ and R ₁₀ together with R ₁₁ each -CH = CH-CH = CH-, R ₅ (CH ₂ ) ₂ SO ₂ (CH ₂ ) ₂ SO ₃ ^⊖ , R ₆ , R ₇ , R ₉ H, R ₈ (CH ₂ ) ₂ SO ₂ (CH ₂ ) ₂ SO ₃ H, n = 0; 595;

LS-XXI-119

X ₁ , X ₂ = S, R ₁ together with R ₂ and R ₁₀ together with R ₁₁ each the remaining members of a 5-methylbenzthiazole, R ₅ , R ₈ C ₂ H ₅ , R ₆ , R ₇ , R ₉ H, Y ^⊖ I ^⊖ , n = 1; 592;

LS-XXI-120

X ₁ , X ₂ = S, R ₁ together with R ₂ and R ₁₀ together with R ₁₁ each -CH = CH-CH = CH-, R ₅ C ₂ H ₅ , R ₆ , R ₉ H, R ₇ CH ₃ , R ₈ CH ₂ -CH (OH) -CH ₂ -SO ₃ ^⊖ , n = 0; 580;

LS-XXI-121

X ₁ , X ₂ = S, R ₁ together with R ₂ and R ₁₀ together with R ₁₁ each the remaining members of a 5-chlorobenzothiazole, R ₅ (CH ₂ ) ₃ SO ₃ ^⊖ , R ₆ , R ₉ H, R ₇ C ₂ H ₅ , R ₈ (CH ₂ ) ₃ SO ₃ H, n = 0; 650;

LS-XXI-122

X ₁ , X ₂ = S, R ₁ together with R ₂

R ₁₀ together with R ₁₁ through the remaining members on the OH group

substituted 5-hydroxybenzthiazole, R ₅ (CH ₂ ) ₃ SO ₃ ^⊖ , R ₆ , R ₉ H, R ₇ , R ₈ CH ₃ , n = 0; 600;

LS-XXI-123

X ₁ , X ₂ = S, R ₁ together with R ₂

R ₁₀ together with R ₁₁ through the remaining members on the OH group

substituted 5-hydroxybenzthiazole, R ₅ (CH ₂ ) ₃ SO ₃ ^⊖ , R ₆ , R ₉ H, R ₈ CH ₃ , R ₇ C ₂ H ₅ , n = 0; 640;

LS-XXI-124

X ₁ , X ₂ = S, R ₁ together with R ₂ and R ₁₀ together with R ₁₁ each have the remaining members of a 6-phenoxybenzothiazole, R ₅ , R ₈ CH ₃ , R ₆ , R ₉ H, R ₇ C ₂ H ₅ , Y ^⊖ ClO ₄ ^⊖ , n = 1; 585;

LS-XXI-125

X ₁ = Se, X ₂ = S, R ₁ together with R ₂

R ₁₀ together with R ₁₁ the remaining members a 5-hydroxybenzthiazole, R ₅ (CH ₂ ) ₃ SO ₃ ^⊖ , R ₆ , R ₉ H, R ₇ C ₂ H ₅ , R ₈ CH ₃ , n = 0; 600;

LS-XXI-126

X ₁ = O, X ₂ = Se, R ₁ together with R ₂

R ₁₀ together with R ₁₁ the remaining members of a 5-methyl-6-methoxybenzselenazole, R ₅ (CH ₂ ) ₃ SO ₃ ^⊖ , R ₆ , R ₉ H, R ₇ , R ₈ C ₂ H ₅ , n = 0; 620;

LS-XXI-127

X ₁ = O, X ₂ = S, R ₁ together with R ₂

R ₁₀ together with R _{11 are} the remaining members of a 5-chlorobenzothiazole, R ₅ (CH ₂ ) ₃ SO ₃ ^⊖ , R ₆ , R ₉ H, R ₇ C ₂ H ₅ , R ₈ (CH ₂ ) ₃ SO ₃ H, n = 0; 610;

LS-XXI-128

X ₁ = O, X ₂ = S, R ₁ together with R ₂

R ₁₀ together with R ₁₁ the remaining members of a 5-chlorobenzothiazole, R ₅ (CH ₂ ) ₃ SO ₃ ^⊖ , R ₆ , R ₉ H, R ₇ C ₂ H ₅ , R ₈ (CH ₂ ) ₄ SO ₃ H, n = 0; 610;

LS-XXI-129

X ₁ , X ₂ = Se, R ₁ together with R ₂ and R ₁₀ together with R ₁₁ -CH = CH-CH = CH-, R ₅ , R ₈ C ₂ H ₅ , R ₆ , R ₉ H, R ₇ CH ₃ , Y ^⊖ ClO ₄ ^⊖ , n = 1; 635;

LS-XXI-130

X ₁ = S, X ₂ = NC ₂ H ₅ , R ₁ together with R ₂

R ₁₀ together with R ₁₁

R ₅ (CH ₂ ) ₃ SO ₃ ^⊖ , R ₆ , R ₇ , R ₉ H, R ₈ (CH ₂ ) ₂ CH (CH ₃ ) SO ₃ H, n = 0; 620;

LS-XXI-131

X ₁ = O, X ₂ = Se, R ₁ together with R ₂ the remaining members of a 5-methylbenzoxazole, R ₁₀ together with R ₁₁ the remaining members of a 5-methyl-6-methoxybenzselenazole, R ₅ (CH ₂ ) ₃ SO ₃ ^⊖ , R ₆ , R ₉ H, R ₇ , R ₈ C ₂ H ₅ , n = 0; 620;

LS-XXI-132

X ₁ = S, X ₂ = Se, R ₁ together with R ₂ and R ₁₀ together with R ₁₁ each -CH = CH-CH = CH-, R ₅ (CH ₂ ) ₂ SO ₂ (CH ₂ ) ₂ SO ₃ ^⊖ , R ₆ , R ₉ H, R ₇ CH ₃ , R ₈ C ₂ H ₅ , n = 0; 590;

LS-XXII-133

X ₂ = C (CH ₃ ) ₂ , R ₁ together with R ₂ and R ₁₀ together with R ₁₁ each -CH = CH-CH = CH-, R ₅ - (CH ₂ ) ₄ -SO ₃ ^⊖ , R ₆ , R ₇ , R ₉ H, R ₈ CH ₃ , n = 0; 580.

Sensitizers can be dispensed with if for intrinsic sensitivity in a certain spectral range of the silver halide is sufficient, for example the blue sensitivity of silver bromide iodides.

Color coupler for generating the blue-green partial color image are usually couplers of the phenol or α-naphthol type and of the pyrazolopyrrole type.

Color coupler for generating the purple partial color image are usually couplers of the 5-pyrazolone type Indazolons or the pyrazoloazole.

Color coupler for generating the yellow partial color image are usually couplers with an open chain ketomethylene grouping, in particular couplers of the type α-acylacetamids; suitable examples are α-benzoylacetanilide couplers and α-pivaloylacetanilide couplers.

The color couplers can be 4-equivalent couplers, but also act as 2-equivalent couplers. Latter are derived from the 4-equivalent couplers in that they contain a substituent in the coupling point, which is split off at the clutch.

The couplers usually contain a ballast residue, diffusion within the material, i.e. either within a shift or from shift to shift, impossible to make. Instead of couplers with one Ballast residues can also be used with high molecular weight couplers become.

Suitable color couplers or references in which such are described in Research Disclosure 17 643 (1978), Chapter VII.

High molecular weight color couplers are for example in DE-C-1 297 417, DE-A-24 07 569, DE-A-31 48 125, DE-A-32 17 200, DE-A-33 20 079, DE-A-33 24 932, DE-A-33 31 743, DE-A-33 40 376, EP-A-27 284, US-A-4 080 211 described. The high molecular color couplers are used in usually by polymerization of ethylenically unsaturated monomeric color couplers. You can but also obtained by polyaddition or polycondensation become.

Incorporation of couplers or other connections in silver halide emulsion layers can in the way done that first of the connection in question a solution, a dispersion or an emulsion and then the pouring solution for that one Layer is added. Choosing the right one Solvent or dispersant depends on the particular Solubility of the compound.

Methods of introducing into water essentially are insoluble compounds by grinding processes for example in DE-A 26 09 741 and DE-A 26 09 742 described.

Hydrophobic compounds can also be made using high-boiling solvents, so-called oil formers, be introduced into the casting solution. Appropriate Methods are described, for example, in US Pat. No. 2,322,027, US Pat 2 801 170, US-A 2 801 171 and EP-A 0 043 037.

Instead of the high-boiling solvents, oligomers can or polymers, so-called polymeric oil formers Find.

The compounds can also be in the form of loaded latices be introduced into the casting solution. Is referred for example on DE-A 25 41 230, DE-A 25 41 274, DE-A 28 35 856, EP-A 0 014 921, EP-A 0 069 671, EP-A 0 130 115, U.S. 4,291,113.

The diffusion-resistant storage of anionic water-soluble Compounds (e.g. from dyes) can also be used With the help of cationic polymers, so-called pickling polymers respectively.

Suitable oil formers are e.g. Alkyl phthalate, Phosphonic acid esters, phosphoric acid esters, citric acid esters, Benzoic acid esters, amides, fatty acid esters, trimesic acid esters, Alcohols, phenols, aniline derivatives and Hydrocarbons.

Examples of suitable oil formers are dibutyl phthalate, Dicyclohexyl phthalate, di-2-ethylhexyl phthalate, decyl phthalate, Triphenyl phosphate, tricresyl phosphate, 2-ethylhexyl diphenyl phosphate, Tricyclohexyl phosphate, tri-2-ethylhexyl phosphate, Tridecyl phosphate, tributoxyethyl phosphate, Trichloropropyl phosphate, di-2-ethylhexylphenyl phosphate, 2-ethylhexyl benzoate, dodecyl benzoate, 2-ethylhexyl p-hydroxybenzoate, Diethyldodecanamide, N-tetradecylpyrrolidone, Isostearyl alcohol, 2,4-di-tert-amylphenol, Trioctyl citrate, N, N-dibutyl-2-butoxy-5-tert-octylaniline, Paraffin, dodecylbenzene and diisopropylnaphthalene.

The photographic material can also contain UV light-absorbing compounds, white toners, spacers, filter dyes, formalin scavengers, white couplers, light stabilizers, antioxidants, D _Min dyes, additives to improve dye, coupler and white stabilization and to reduce the color fog, plasticizers (latices ), Biocide and others contain.

Compounds that absorb UV light are said to be on the one hand the image dyes before fading by UV-rich Protect daylight and on the other hand as filter dyes the UV light in daylight during exposure absorb and thus improve the color rendering of a film. Usually for the two tasks Connections of different structures are used. Examples are aryl-substituted benzotriazole compounds (US-A 3 533 794), 4-thiazolidone compounds (US-A 3,314,794 and 3,352,681), benzophenone compounds (JP-A 2784/71), cinnamic acid ester compounds (US-A 3,705,805 and 3,707,375), butadiene compounds (US-A 4,045,229) or Benzoxazole compounds (US-A 3 700 455).

Ultraviolet absorbing couplers (such as Cyan couplers of the α-naphthol type) and ultraviolet absorbing Polymers are used. These ultraviolet absorbents can be done by pickling in a special Layer fixed.

Include filter dyes suitable for visible light Oxonol dyes, hemioxonol dyes, styryl dyes, Merocyanine dyes, cyanine dyes and Azo dyes. Of these dyes, oxonol dyes, Hemioxonol dyes and merocyanine dyes used particularly advantageously.

Suitable whiteners are e.g. in Research Disclosure 17,643 (Dec. 1978), Chapter V, in US-A 2,632,701, 3,269,840 and in GB-A 852 075 and 1 319 763.

Certain layers of binder, especially that of Carrier most distant layer, but also occasionally Intermediate layers, especially if they during the manufacturing process the furthest from the wearer represent removed layer, can be photographically inert Contain particles of inorganic or organic nature, e.g. as a matting agent or as a spacer (DE-A 33 31 542, DE-A 34 24 893, Research Disclosure 17 643, (Dec. 1978), Chapter XVI).

The average particle diameter of the spacers is in particular in the range from 0.2 to 10 µm. The Spacers are insoluble in water and can be insoluble in alkali or be alkali-soluble, the alkali-soluble generally in an alkaline development bath be removed from the photographic material. Examples suitable polymers are polymethyl methacrylate, Copolymers of acrylic acid and methyl methacrylate and hydroxypropylmethyl cellulose hexahydrophthalate.

Additives to improve the dye, coupler and White stability and to reduce the color fog (Research Disclosure 17 643/1978, Chapter VII) can belong to the following chemical substance classes: Hydroquinones, 6-hydroxychromanes, 5-hydroxycoumarans, Spirochromanes, spiroindanes, p-alkoxyphenols, steric hindered phenols, gallic acid derivatives, methylenedioxybenzenes, Aminophenols, sterically hindered amines, derivatives with esterified or etherified phenolic Hydroxyl groups, metal complexes.

Compounds that have both a sterically hindered amine partial structure as well as a sterically hindered phenol partial structure in one molecule (US-A 4,268,593) are particularly effective in preventing Impairment (deterioration or degradation) of yellow Color images as a result of the development of heat, Moisture and light. To the impairment (deterioration or the degradation) of purple color images, especially their impairment (deterioration or degradation) as a result of exposure to light, to prevent are Spiroindane (JP-A 159 644/81) and Chromane by hydroquinone diether or monoether substituted (JP-A 89 835/80) are particularly effective.

The layers of the photographic material can with the usual hardening agents are hardened. Suitable Hardening agents are e.g. Formaldehyde, glutaraldehyde and similar aldehyde compounds, diacetyl, cyclopentadione and similar ketone compounds, bis (2-chloroethyl urea ), 2-hydroxy-4,6-dichloro-1,3,5-triazine and others Compounds containing reactive halogen (US-A 3,288,775, US-A 2,732,303, GB-A 974 723 and GB-A 1 167 207) divinyl sulfone compounds, 5-acetyl-1,3-diacrylhexahydro-1,3,5-triazine and other connections, which contain a reactive olefin bond (US-A 3,635,718, U.S. 3,232,763 and GB 994,869); N-hydroxymethylphthalimide and other N-methylol compounds (US-A 2,732,316 and US-A-2,586,168); Isocyanates (US-A 3,103,437); Aziridine compounds (US-A 3,017,280 and US-A 2,983,611); Acid derivatives (US-A 2 725 294 and US-A 2,725,295); Carbodiimide-type compounds (US-A 3 100 704); Carbamoylpyridinium salts (DE-A 22 25 230 and DE-A 24 39 551); Carbamoyloxypyridinium compounds (DE-A 24 08 814); Compounds with a phosphorus-halogen bond (JP-A 113 929/83); N-carbonyloximide compounds (JP-A 43353/81); N-sulfonyloximido compounds (US-A 4,111,926), dihydroquinoline compounds (US-A 4,013,468), 2-sulfonyloxypyridinium salts (JP-A 110 762/81), formamidinium salts (EP-A 0 162 308), compounds with two or more N-acyloximino groups (US-A 4,052,373), epoxy compounds (US-A 3,091,537), compounds of the isoxazole type (US-A 3,321,313 and US-A 3 543 292); Halocarboxyaldehydes such as mucochloric acid; Dioxane derivatives such as dihydroxydioxane and di-chlorodioxane; and inorganic hardeners such as chrome alum and zirconium sulfate.

The hardening can be effected in a known manner be that the curing agent of the casting solution for the layer to be hardened is added, or in that the layer to be hardened is covered with a layer which contains a diffusible hardening agent.

Among the classes listed there are slow-acting ones and fast-acting hardeners and so-called Instant hardeners that are particularly beneficial. Under Immediate hardeners are understood as connections that are suitable Crosslink the binder so that immediately after Watering, at the latest after 24 hours, preferably at the latest after 8 hours the curing is completed is that no more through the crosslinking reaction conditional change in sensitometry and swelling of the Shift association occurs. Under swelling the Difference between wet film and dry film thickness understood in the aqueous processing of the film (Photogr. Sci., Eng. 8 (1964), 275; Photogr. Sci. Eng. (1972), 449).

These hardening agents that react very quickly with gelatin is it e.g. carbamoylpyridinium salts, those with free carboxyl groups of gelatin able to react, so that the latter with free Amino groups of the gelatin to form peptide bonds and crosslinking of the gelatin react.

There are diffusible hardeners that work on everyone Layers within a layer group in the same Wise hardening. But there are also shift-limited ones acting, non-diffusing, low molecular weight and high molecular hardener. With them you can individual Layers, e.g. the protective layer is particularly strong network. This is important when looking at the silver halide layer little because of the increase in silver opacity hardens and with the protective layer the mechanical Properties must improve (EP-A 0 114 699).

The color photographic materials according to the invention are usually processed by developing, bleaching, fixing and washing or stabilizing without subsequent washing, whereby bleaching and fixing can be combined into one processing step. All developing compounds which have the ability to coexist in the form of their oxidation product can be used as the color developer compound Color couplers to react to azomethine or indophenol dyes. Suitable color developer compounds are aromatic compounds of the p-phenylenediamine type containing at least one primary amino group, for example N, N-dialkyl-p-phenylenediamines such as N, N-diethyl-p-phenylenediamine, 1- (N-ethyl-N-methanesulfonamidoethyl) -3 -methyl-p-phenylenediamine, 1- (N-ethyl-N-hydroxyethyl) -3-methyl-p-phenylenediamine and 1- (N-ethyl-N-methoxyethyl) -3-methyl-p-phenylenediamine. Other useful color developers are described, for example, in J. Amer. Chem. Soc. 73 , 3106 (1951) and G. Haist, Modern Photographic Processing, 1979, John Wiley and Sons, New York, page 545 ff.

After color development, an acidic stop bath or follow a watering.

Usually the material after color development bleached and fixed. As bleaching agents e.g. Fe (III) salts and Fe (III) complex salts such as ferricyanides, Dichromate, water-soluble cobalt complexes used become. Iron (III) complexes are particularly preferred of aminopolycarboxylic acids, especially e.g. from Ethylenediaminetetraacetic acid, propylenediaminetetraacetic acid, Diethylenetriaminepentaacetic acid, nitrilotriacetic acid, Alanine diacetic acid, iminodiacetic acid, N-hydroxyethyl-ethylenediamine triacetic acid, Alkyliminodicarboxylic acids and of corresponding phosphonic acids. Suitable persulphates and peroxides are also bleaches, e.g. Hydrogen peroxide.

The bleach-fixing bath or fixing bath is usually followed by one Irrigation, which is carried out as countercurrent irrigation and consists of several tanks with their own water supply.

Favorable results can be obtained by using one following final bath, which has little or no formaldehyde contains.

However, the watering can be completed by a stabilizing bath to be replaced, usually in countercurrent to be led. This stabilizing bath takes over when formaldehyde is added also the function of a final bath.

The color photographic material according to the invention can are also subject to a reversal trend. Here the color development go with a first development Developer who has no dye with the couplers forms, and a diffuse second exposure or chemical veil ahead.

It is preferably the one according to the invention However, material is a color negative material, in particular Color negative paper or display material.

Examples

A color photographic recording material which is suitable for a rapid processing process was produced by applying the following layers in the order given to a paper coated on both sides with polyethylene. The quantities given relate to 1 m ² . The corresponding amounts of AgNO ₃ are given for the silver halide application.

example 1 Layer structure 1

1st layer (substrate layer)
0.2 g gelatin

2nd layer (blue-sensitive layer)
blue-sensitive silver halide emulsion (99.5 mol% chloride, 0.5 mol%. bromide, average grain diameter 0.78 µm) from 0.50 g AgNO ₃ , sensitization maximum 480 nm with
1.38 g gelatin
0.60 g yellow coupler Y-1
0.48 g tricresyl phosphate (CPM)

3rd layer (intermediate layer)
1.18 g gelatin
0.08 g 2,5-dioctyl hydroquinone
0.08 g dibutyl phthalate (DBP)

4th layer (green-sensitive layer)
green-sensitized silver halide emulsion (99.5 mol% chloride, 0.5 mol% bromide, average grain diameter 0.37 µm) from 0.40 g AgNO ₃ , sensitization maximum 550 nm with
1.02 g gelatin
0.37 g purple coupler M-1
0.40 g DBP

5th layer (intermediate layer)
1.20 g gelatin
0.66 g UV absorber of the formula

0.052 g 2,5-dioctyl hydroquinone
0.36 g CPM

6th layer (red-sensitive layer)
red-sensitized silver halide emulsion (99.5 mol% chloride, 0.5 mol% bromide, average grain diameter 0.35 µm) from 0.28 g AgNO ₃ , sensitization maximum 708 nm with
0.84 g gelatin
0.39 g of cyan coupler C-1
0.39 g CPM

7th layer (UV protective layer)
0.65 g gelatin
0.21 g UV absorber as in 5th layer
0.11 g CPM

8th layer (protective layer)
0.65 g gelatin
0.39 g of curing agent of the formula

Example 2 (comparison)

It became a color photographic recording material which differs from Example 1 in that that the red sensitive emulsion in layer 6 additionally green-sensitized with GS 1 (50 µmol / mol Ag) has been.

Example 3 (comparison)

It became a color photographic recording material prepared, which is described in Example 1 differs in that the layer 6 additional was blue-sensitized with 100 µmol / mol Ag BS-1.

Example 4 (Invention)

A color photographic recording material was produced which differs from Example 1 in that the red-sensitive layer containing a cyan coupler contains an additional silver halide emulsion (99.5 mol% chloride, 0.5 mol% bromide, average grain diameter 0.4 μm) contains 0.1 g of AgNO ₃ , which has been gap-sensitized with LS-IV-53 (20 μmol / mol Ag).

Example 5 (Invention)

It became a color photographic recording material which differs from Example 1 in that that the red-sensitive emulsion additionally with LS-I-1 (100 µmol / mol Ag) was gap-sensitized.

Example 6 (Invention)

It became a color photographic recording material which differs from Example 1 in that that the blue-sensitive emulsion additionally with LS-XXI-106 (100 µmol / mol Ag) gap-sensitized has been.

The materials were subjected to the following exposures a), b), c) or d) subjected and in the specified process processed.

a) durch einen Stufenkeil mit Filter, der durchlässig für grünes Licht ist.

b) durch einen Stufenkeil mit Filter, der durchlässig für blaues Licht ist.

c) durch einen Stufenkeil mit einem Filter, der durchlässig für blaues und grünes Licht ist und einen zusätzlichen Purpur- und Gelb-Filter, so daß auf dem verarbeiteten Material über den gesamten Dichtebereich ein klares Rot entsteht.

d) durch einen Stufenkeil mit einem Filter, der für rotes und grünes Licht durchlässig ist und einem Purpurfilter um ein klares Blau zu erzeugen.

exposure

a) through a step wedge with filter that is permeable to green light.

b) through a step wedge with filter that is transparent to blue light.

c) by a step wedge with a filter that is permeable to blue and green light and an additional purple and yellow filter, so that a clear red arises on the processed material over the entire density range.

d) by a step wedge with a filter that is transparent to red and green light and a purple filter to produce a clear blue.

a) die Zahl der erkennbaren Stufen und

b) bei Dichte 2,0 in Purpur (PP) oder Gelb (GB) der prozentuale Anteil von Blaugrün (BG) bestimmt (= Nebendichte, ND); ND_BG=[(D_BG bei D_PP=2,0)/D_PP=2,0] · 100.

After that

(a) the number of noticeable levels and

b) at density 2.0 in purple (PP) or yellow (GB) the percentage of blue-green (BG) is determined (= secondary density, ND); ND _BG = [(D _BG at D _PP = 2.0) / D _PP = 2.0] * 100.

Result:

material exposure Number of levels [%] ND _BG 1 a 15 10.0 comparison 1 b 15 3.0 comparison 1 c 16 - comparison 1 d 16 - comparison 2nd a 17th 13.5 comparison 2nd c 17th - comparison 3rd b 16 8.0 comparison 3rd c 17th - comparison 4th a 17th 10.2 invention 4th b 16 3.0 invention 4th c 21 - invention 5 a 17th 10.0 invention 5 b 15 3.2 invention 5 c 21 - invention 6 a 17th 10.3 invention 6 d 20th - invention

The examples show that the invention has a higher Number of levels that can be developed and a better detail drawing for the important red rendering (exposure c)) is obtained without the otherwise occurring at the same time Desaturation of the colors purple (exposure a)) or Yellow (exposure b)) as in comparison material 2 or 3rd

Sensibilisierungsmaximum: 708 nm

Sensibilisierungsmaximum: 480 nm

Sensibilisierungsmaximum: 550 nm

a) Farbentwickler - 45 s - 35°C Triethanolamin 9,0 g/l NN-Diethylhydroxylamin 4,0 g/l Diethylenglykol 0,05 g/l 3-Methyl-4-amino-N-ethyl-N-methansulfonamidoethyl-anilin-sulfat 5,0 g/l Kaliumsulfat 0,2 g/l Triethylenglykol 0,05 g/l Kaliumcarbonat 22 g/l Kaliumhydroxid 0,4 g/l Ethylendiamintetraessigsäure di-Na-Salz 2,2 g/l Kaliumchlorid 2,5 g/l 1,2-Dihydroxybenzol-3,4,6-trisulfonsäure-trinatriumsalz auffüllen mit Wasser auf 1.000 ml; pH 10,2 0,3 g/l

b) Bleichfixierbad - 45 s - 35°C Ammoniumthiosulfat 75 g/l Natriumhydrogensulfit 13,5 g/l Ammoniumacetat 2,0 g/l Ethylendiamintetraessigsäure (Eisen-Ammonium-Salz) 57 g/l Ammoniak 25 Gew.-%ig 9,5 g/l Essigsäure 9,0 g/l auffüllen mit Wasser auf 1.000 ml; pH 5,5

c) Wässern - 2 min - 33°C

D) Trocknen

Comparative samples and material according to the invention were exposed to a color negative (image motif) and processed in the specified process. The material according to the invention shows a significantly better tracing in the area of high red densities than the comparative samples of examples 1, 2 and 3, less color distortion at high purple densities than the comparative sample according to example 2 and less color distortion at high yellow densities than the comparative sample from Example 3.

Sensitization maximum: 708 nm

Sensitization maximum: 480 nm

Sensitization maximum: 550 nm

a) Color developer - 45 s - 35 ° C Triethanolamine 9.0 g / l NN-diethylhydroxylamine 4.0 g / l Diethylene glycol 0.05 g / l 3-methyl-4-amino-N-ethyl-N-methanesulfonamidoethyl aniline sulfate 5.0 g / l Potassium sulfate 0.2 g / l Triethylene glycol 0.05 g / l Potassium carbonate 22 g / l Potassium hydroxide 0.4 g / l Ethylenediaminetetraacetic acid di-Na salt 2.2 g / l Potassium chloride 2.5 g / l 1,2-Dihydroxybenzene-3,4,6-trisulfonic acid trisodium salt make up to 1,000 ml with water; pH 10.2 0.3 g / l

b) bleach-fix bath - 45 s - 35 ° C Ammonium thiosulfate 75 g / l Sodium bisulfite 13.5 g / l Ammonium acetate 2.0 g / l Ethylenediaminetetraacetic acid (iron ammonium salt) 57 g / l Ammonia 25% by weight 9.5 g / l acetic acid 9.0 g / l make up to 1,000 ml with water; pH 5.5

c) Soak - 2 min - 33 ° C

D) drying

Claims (7)

1. Colour photographic silver halide material having at least one cyan-coupling silver halide emulsion layer containing a red sensitiser, at least one magentacoupling silver halide emulsion layer containing a green-sensitiser and at least one yellow-coupling silver halide emulsion layer containing a blue-sensitiser on a support, characterised in that the blue-sensitive silver halide emulsion layer, of which there is at least one, contains a further spectral sensitiser (gap sensitiser), the sensitisation maximum of which is between the sensitisation maxima of the red- and green-sensitive and/or the red-sensitive silver halide emulsion layer, of which there is at least one, contains a furcher spectral sensitiser, the sensitisation maximum of which is between the sensitisation maxima of the green- and blue-sensitive silver halide emulsion layers.
2. Colour photograpric silver halide material according to claim 1, characterised in that the sensitisation maximum of the gap sensitiser is at least 15 nm away from the absorption maxima of the green or blue sensitisers and at least 30 nm away from the absorption maximum of the red sensitiser.
3. Colour photographic silver halide material according to claim 1, characterised in that the gap sensitiser is of one of the formulae I to XI, XXVI and XXVII

   

   

   

   

   

   

   

   

   

   

   

   

   

   in which

   X₁ -X₆

   mean O, NR₁, S, Se, Te, P(R₁), P(R₁)₃, CH₂, CHR₂, C(R₂)₂

   R₁

   means alkyl, optionally substituted sulfoalkyl, carboxyalkyl, aryl, in particular phenyl

   R₂

   means aryl, in particular phenyl, alkyl, in particular having 1 to 5 C atoms, CN

   R₃, R₄, R₅, R₆, R₁₉ R₂₀, R₂₁, R₂₂

   mean hydrogen, halogen, alkoxy, aryloxy, cyano, hydroxy, sulfo, carboxy, alkoxycarbonyl, aryloxycarbonyl, acylaminosulfonyl, aminosulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, arylaminosulfonyl, diarylaminosulfonyl, aryl, arylmercapto, alkylmercapto or alkyl or

   R₃ and R₆ or R₁₉ and R₂₂

   together mean a π bond

   R₄ and R₅ or R₂₀ and R₂₁

   together mean a 3- to 12-membered ring, which may contain heteroatoms and multiple bonds,

   R₄ and R₅ or R₂₀ and R₂₁

   together mean a 3- to 12-membered ring, which may contain heteroatoms and multiple bonds,

   R₇, R₈, R₉

   mean alkyl, optionally substituted sulfoalkyl, carboxyalkyl or aryl

   R₁₀, R₁₁, R₁₂

   mean hydrogen, halogen, cyano, aryl, aryloxy, arylmercapto, alkyl, alkoxy or alkylmercapto

   R₁₃, R₁₄, R₁₅, R₁₆ R₁₇, R₁₈, R₂₃, R_24, R₂₅, R₂₆

   mean hydrogen, halogen, alkoxy, cyano, hydroxy, sulfo, carboxy, alkoxycarbonyl, aryloxycarbonyl, acylaminosulfonyl, aminosulfonyl, alkylaminosulfonyl, arylaminosulfonyl, diarylaminosulfonyl, aryl, aryloxy, arylmercapto, alkyl or alkylmercapto,

   R₄₈

   means hydrogen, alkyl, sulfoalkyl, carboxyalkyl, acyl or a negative charge,

   R₄₉

   means -CN, -CON(R₁)₂ or -SO₂R₁,

   Z

   means the remaining members of a 3- to 12-membered ring, which may contain heteroatoms and double bonds,

   M^⊕

   means a cation,

   Y^⊖

   means an anion and

   n

   means 0 or 1.

4. Colour photographic silver halide material according to claim 1, characterised in that the gap sensitiser is of one of the formulae XII to XIX

   

   

   

   

   

   

   

   in which

   X

   means 0, S, Se, NR₁,

   R₂₇, R₂₈

   mean H, CH₃, phenyl, 2-furyl, Cl, methoxycarbonyl, ethoxycarbonyl,

   R₂₉, R₃₂, R₃₅, R₃₈, R₃₉, R₄₀, R₄₂, R₄₃, R₄₅, R₄₇

   mean methyl, ethyl, sulfoalkyl, carboxyalkyl,

   R₃₀, R₃₁

   mean hydrogen or R₂₉,

   R₃₃

   means hydrogen, methyl, ethyl,

   R₃₄

   means H, CN,

   R₃₆, R₃₇

   mean H, CH₃, C₂H₅, phenyl, ethoxy, morpholinocarbonyl, 1-hydroxyisopropyl, Cl, methoxycarbonyl, ethoxycarbonyl,

   R₄₁

   means H, Cl, CH₃, OH, OCH₃, phenyl,

   R₄₄

   means H, OCH₃,

   R₄₆

   means H, CH₃, SCH₃, Cl, phenyl.

5. Colour photographic silver halide material according to claim 1, characterised in that the gap sensitiser is of one of the formulae XX to XXII

   

   

   

   in which

   R₁, R₂, R₃, R₄, R₁₀, R₁₁

   mean hydrogen, halogen, alkoxy, aryloxy, cyano, hydroxy, sulfo, carboxy, alkoxycarbonyl, aryloxycarbonyl, acylaminosulfonyl, aminosulfonyl, alkylaminosulfonyl, dialkylaminosulfonyl, arylaminosulfonyl, diarylaminosulfonyl, aryl, arylmercapto, alkylmercapto or alkyl or

   R₁ and R₂

   together or R₂ and R₃ or R₃ and R₄ together or R₁₀ and R₁₁ together mean an aromatic or heteroaromatic 3- to 12-membered ring, in particular a fused benzo or naphtho ring,

   R₅, R₈

   mean aryl, alkyl, optionally OH-substituted sulfoalkyl, carboxyalkyl,

   R₆, R₇, R₉

   mean hydrogen, halogen, cyano, aryl, arylmercapto, aryloxy, alkyl, alkylmercapto or alkoxy,

   X₁, X₂, X₃, X₄

   mean 0, NR, S, Se, Te, PR, PR₃, CH₂, CH-alkyl, C(alkyl)₂, CH aryl, C(aryl)₂,

   Y^⊖

   means an anion and

   n

   means 0 or 1.

6. Colour photographic silver halide material according to claim 5, characterised in that the gap sensitiser is of one of the formulae XXIII to XXV

   

   

   

   in which

   R₁₂, R₁₃, R₁₈

   mean H or CH₃,

   R₁₄, R₁₅

   mean H, CH₃, Cl or phenyl,

   R₁₆, R₁₇, R₁₉, R₂₀

   mean H, CH₃, Cl, phenyl or
   R₁₆ together with R₁₇ or R₁₉ together with
   R₂₀ mean the remaining members of an optionally substituted aromatic or heteroaromatic ring
   and

   R₅, R₈, X₁ and X₂

   have the meaning stated in claim 5.

7. Colour photographic silver halide material according to claim 1, characterised in that the gap sensitiser of the formulae I to XI, XXVI, XXVII, XII to XIX, XX to XXII and XXIII to XXV according to claims 3 to 6 is added to the emulsion after chemical ripening.