DE1285885B - Color photographic recording material - Google Patents

Description

The invention relates to a color photographic recording material, which contains a yellow coupler which is soluble in organic solvents.

It is known that a color image has better stability against light, heat and moisture achieved when using couplers with oil-soluble groups that are not or only in water sparingly soluble organic solvents (hereinafter referred to as coupler solvents) are dissolved and are dispersed in this form in the emulsion.

These so-called protective couplers must have fully adequate photographic properties, e.g. B. with regard to coupling efficiency and speed, fogging, hue, etc. In addition, must they be sufficiently soluble in a coupler solvent and readily dispersible in the emulsion. the numerous known protecting couplers are either not sufficiently soluble in the coupler solvents or not sufficiently dispersible in the emulsion, or it is too costly to manufacture.

There are e.g. B. Couplers having a dialkylphenoxy group (U.S. Patent 2,875,057) or with a dialkylcyclohexyloxy group (U.S. Patent 2,920,961). The cost of making The starting materials required for this connection are very important, as are the photographic properties are not "satisfactory in all respects."

The object of the invention is to provide a fetegrafisdies material containing a yellow coupler e! the yellow coupler TiTXüpplerlösung is ^ well soluble, leads to an excellent coupling effect and color tone and is also cheap to manufacture.

The invention is based on color photographic material in a silver halide layer as Yellow coupler contains and is a benzoylacetanilide with a substituent in the 5-position in the anilide nucleus characterized in that the yellow coupler is an ester of m- (benzoylacetamino) benzoic acid with the general formula

with at least 8 carbon atoms, in the 5-position of the anilide nucleus. This is the yellow coupler Protected against diffusion out of the emulsion. The melting point of the coupler is low. There in general organic esters are used as the coupler solvent, the coupler has a carboxylic acid ester group good affinity for coupler solvents, and solubility as well as dispersibility in the emulsion are excellent.

The coupler having a carboxylic acid ester group has very good coupling efficiency and speed, which is due to the fact that the carboxylic ester group has large electron attraction has, whereby the coupling efficiency and speed is favorably influenced.

By means of a lower alkoxy group or a halogen atom in the ortho position of the anilide nucleus, the Coupling ability and speed as well as the color shade positively influenced.

The starting materials required for the production of such couplers, such as benzoylacetate, 3-amino-4-methoxybenzoic acid, 3-Amino-4-chlorobenzoic acid and its esters as well as lauryl alcohol are considered to be widespread Commercial products available at low prices, and the synthesis takes place in two or more three stages so that the couplers are comparatively very cheap.

With the same weight of a coupler dispersed in the emulsion, the effectiveness is one Low molecular weight coupler in general, the number of molecules present larger than a ^ üppier ~ vörFnoHereiir Molecular weight. If in the general formula I X is a hydrogen atom, R is a dodecyl group (this has a sufficient anti-diffusion effect) and Y is a methoxy group (formula V) or a Is chlorine atom (Formula XIII), then the molecular weight of the coupler is 481 and 485.5, respectively and is about 13% lower than that of a yellow coupler having a dialkylphenoxy group. For example has the yellow coupler of the formula

COOR NHCOCH ₇ O-

COCHCONH X

45 COCH ₉ CONH

OCH ₃

in which R is a straight or branched alkyl group with at least 8 carbon atoms or an aliphatic radical with at least 8 carbon atoms and at least one ether bond, Y a hydrogen atom, a lower alkoxy group or a / halogen atom and X represents a hydrogen or halogen atom.

The yellow couplers used according to the invention are new compounds disclosed in US Pat a simple process using readily available and inexpensive raw materials can be. Regarding the photographic properties, such as coupling efficiency and speed, Fogging, hue, etc. will produce excellent results. The durability the color image against light, heat and moisture is also excellent.

As can be seen from the general formula, the coupler according to the invention carries as substituents a carboxylic ester group which is an alkyl group

50

C ₅ H _u - (t)

a molecular weight of 558. From these facts it can be seen that the couplers according to the invention exhibit improved coupling efficiency and result in a high density yellow image.

In attempts to lower the molecular weight and to increase the coupling efficiency the following was found: If R is an octyl group (8 carbon atoms), the coupler has a sufficient one Diffusion resistance, so that no undesirable side effects occur in this regard. On the other hand, it is very soluble in coupler solvents and dispersible in the emulsion. If X is a hydrogen atom, R is an octyl group and Y is a methoxy group (Formula III) or a chlorine atom (Formula XI), the very advantageous molecular weight is obtained of 425 and 429.5, respectively.

Molecular weights and solubility of couplers to be used according to the invention are given in Table 1 specified.

Table 1 COOR

<f ~ \ - COCH ₂ CONH - / \

Structural formula

Molecular weight

Tuesday

Solubility*)

Tri. Ethyl acetate

- C10H21

- C12H25

- CH ₂ CH (C ₂ H ₅ ) (CH ₂ ) ₃ CH ₃

- (CH ₂ ) 7CH (CH ₃ ) 2

Ill -OCH ₃ -C ₈ Hi ₇

IV -OCH ₃ -Ci ₀ H ₂ I.

V -OCH ₃ -C12H25

VI -OCH ₃ - Ci ₄ H ₂₉

VII -OCH ₃

XI -Cl

XII -Cl

XIII -Cl

XIV-Cl

XV -Cl

*) = G / l00 g of solvent (25 ⁰ C).
Di. = dibutyl phthalate.
Tri. = Tributyl phosphate.

Another advantage is that a greater amount of coupler will disperse in the emulsion can be used by using a coupler which has higher solubility in the coupler solvent Has. This also promotes the coupling effectiveness and thus the color density. From table 1 it can be seen that the couplers according to the invention have excellent solubility, especially in Esters such as phthalic acid esters, phosphoric acid esters and acetic acid esters. This also takes place including an extremely low or slow precipitation of coupler crystals when the Coupler solution is in a supercooled state. If in formula I X is a hydrogen atom and

Y is a chlorine atom (formulas XI, XII, XIII), then the melting point is 22 to 36 ⁰ C higher than when

Y is a methoxy group even if R is the same substituent in both cases. The solubility in a coupler solvent is less than one third less than when R is a methoxy group.

It has also been found that the melting point is lowered and the solubility is increased considerably, when Y is a chlorine atom and R is a branched alkyl chain instead of a straight alkyl chain chooses. Such couplers with increased solubility can be easily produced if one does this commercially available aliphatic alcohols with side chains, such as 2-ethylhexanol, isodecyl alcohol or triisodecyl alcohol is used.

With the couplers according to the invention one achieves, in particular due to their very much higher Solubility, a significant improvement in the density of the color image, hue, transparency and the resistance of the color photographic material to light, heat and moisture.

The number of carbon atoms of the substituent R can be an odd number, but in view of the accessibility, purity and price of the 425

453

481

509

537

429.5

457.5

485.5

429.5

457.5

30th
15th

21 2y 24

1.5
41
80

40
61
53
56
25th
8th

1.0
110
163

28.2
26.8
22.4
29.4
29.8
15.11
10.5
6.2
23.8
47.6

The substances concerned are generally preferred to residues with an even C number.

As already mentioned, the starting material for introducing the radical R can be an aliphatic Be alcohol with a straight or branched chain. This can also have one or more ether bonds included, e.g. B. Alcohols according to the general formulas

HO (CH ₂ LO- (CHACH ₃

or HO (CH ₂ ) _m - O - (CH ₂ ) n - O - (CH ₂ ) _P CH ₃

In these formulas, m, η and ρ are integers greater than 1 and m + n ^ 7, as it is e.g. B. is the case with diethylene glycol monobutyl ether. In general, higher alcohols with at least 8 carbon atoms can be used with advantage as starting material for the introduction of the radical R.

As can be seen from Synthesis Example 3 below, in the case of the coupler according to the invention an active methylene hydrogen atom can easily be exchanged for a halogen atom. There a such halogen-substituted coupler with 2 equivalents of silver ion forms the color, one has the The advantage is that half of the silver ions produce the same color.

The numerical values given in Table 1 for the solubility relate to room temperature. However, the solubility rises sharply with temperature, and at an elevated temperature one can achieve a considerable Dissolve amount of coupler in poor solubility. This solution can be used for practical application disperse in gelatin and mix the dispersion into the photographic emulsion. In the exemplary embodiments Examples 3, 5 and 9 relate to a method using a high-boiling solvent, while in the

Examples 7 and 8 a low-boiling solvent and Examples 1 and 2 both kinds of Solvents are used.

The couplers according to the invention can also be incorporated into the photographic emulsion in other ways 2. B. a low melting point coupler can be mixed by heating in a Liquid can be melted and dispersed in this form in gelatin (cf. Example 6). Further it can be added to the emulsion as an alkaline aqueous solution (cf. Example 4).

In all of these different blending processes, excellent coupling with color developers is obtained, which contain N, N-disubstituted paraphenylenediamines as a developer.

The yellow image produced with couplers according to the invention shows good transparency and good color rendering as well as a sharp absorption spectrum for blue light from 400 to 480 mix, but none harmful absorption spectrum for green light from 500 to 600 ηΐμ, which reddish tones in yellow of the image. This is a very advantageous absorption characteristic for color photography.

The yellow images produced with known yellow couplers are slightly influenced by external conditions, such as light, heat and moisture, causing discoloration or fading. This is not the case with the couplers according to the invention. Deliver particularly stable images Couplers of the formula I which have a chlorine atom in the ortho position of the anilide nucleus.

Some examples of those constructed in accordance with the invention follow Coupler.

15th

20th

25th

COCH ₂ CONH

COOC ₈ H ₁ ,

(Ill)
OC H3

COOC ₁₀ H ₂₁

(IV)

45

OCH ₃

COOC ₁₂ H ₂₅

1

<^ ^ -COCH ₂ CONH - <^ y

(V)

OCH,

COCH, CONH

COOC ₁₄ H ₂₉

55 /

(VI)

OCH ₃

COOC ₁₆ H ₃₃

COCH ₂ CONH- />

] '(VII)

OCH ₃ COCH ₂ CONH

COOC ₁₈ H ₃₇

] - '· (viii)

OCH ₃

COOC ₈ H ₁₇

COCH ₂ CONH

(IX)

OC ₂ H ₅

COOC ₁₂ H ₂₅

COCH ₇ CONH

OC ₂ H ₅

COOC ₈ H ₁₇ COCH ₂ CONH - <^ ^)

Cl

COOC ₁₀ H ₂₁

COCH ₂ CONH- / V

/ XI)

(XII)

Cl

COOCj ₂ H ₂₅

COCH ₂ CONH-

ι
Cl

(XIII)

-COCHXONH-i

COOCH ₂ CH (CH ₂ J ₃ Ch ₃

COOCH ₂ C (CH ₂ I ₇ CH ₃

CH ₃

Cl

(XVI)

COOC ₁₃ H.

12 * * 25

—COCHXONH

- COCH ₇ CONH

-COCH ₁ CONH

COO (CH ₂ ) ₂ OiCH ₂ ) ₂ O (CH ₂ ) ₃ CH ₃

> (XIX)

OCH ₃

COOCH,

12 « ^J 25

(XX)

OCH ₃

COOC ₁₄ H ₂₉

) - COCHCONH

i Cl

-COCHjCONH-K / (XXI)

COOC ₁₂ H ₂₅
- COCHCONH "<> (XXII)

OCH ₃

The following examples are given for the preparation of the couplers:

Synthesis 1

1 a) Production of dodecyl ^ -amino ^ -methoxybenzoate

A four-necked flask of 2 l content was fitted with a stirrer, a thermometer, a connection for Introduction of nitrogen and a connection for distilling off that occurring as a by-product Methanol provided. Into this flask were added 181 g (1 mole) of methyl 3-amino-4-methoxybenzoate and 279 g (1.5 mol) n-bodecyl alcohol given. The contents of the flask was melted at an internal temperature of 80 ° C. Then 2.5 ecm of titanium butoxide were added added and the methanol formed was distilled off with the introduction of nitrogen gas. It was on heated an internal temperature of 170 to 180 C, the transesterification progressed slowly. To About 80% of the theoretical amount of methanol had distilled off in 4 hours. After that it was slow cooled to an internal temperature of 40 to 50 C. and the contents of the flask poured into 1 liter of methanol. After standing overnight, brown crises

stalls secluded. These were sucked off on the filter and washed with 500 ecm of methanol. After drying, 271 g of dodecyl 3-amino-4-methoxybenzoate were obtained in 81% yield. M.p. 47 up to 48 C.

1 b) Preparation of Benzoylaceto-2-methoxy-5-dodecyloxycarbonylanilide (Formula V)

A three-necked flask equipped with a stirrer, thermometer and connection for distilling off the ethanol formed as a by-product was filled with 192 g (1 mol) of ethylbenzoyl acetate and 335 g (1 mol) of the dodecyl-3-amino-4-methoxybenzoate prepared according to the above procedure. After the reaction mixture had been kept at an internal temperature of 150 to 160 ° C. with stirring, the distillation of the ethanol began. About 60 ° / ₀ of the theoretical amount had been distilled off after about 6 hours. Ethanol was then distilled off under reduced pressure for a further 30 minutes without stirring. After slow cooling, the reaction product was poured into 21 petroleum ether. After standing overnight, yellowish white crystals had separated out. These were filtered off with suction, washed with 1 liter of petroleum ether and recrystallized from 1.71 ligroin. 317 g of benzoylaceto - 2 - methoxy - 5 - dodecyloxycarbonylanilide were obtained in a yield of 66%. M.p. 75 to 76 C.

Synthesis 2

2 a) Preparation of dodecyl 3-amino-4-chlorobenzoate

It was worked as under 1 a) with the difference that methyl 3-amino-4-chlorobenzoate in place of methyl 3-amino-4-methoxybenzoate was used. The resulting crystals were made from methanol recrystallized. Dodecyl S-aniino ^ chlorobenzoate was obtained in 79% yield. M.p. 60 up to 62 C.

2 b) Production of Benzoylaceto ^ -chlor-S-dodecyloxycarbonylanilide (Formula XIII)

The procedure was as in 1 b) with the difference that dodecyl 3-amino-4-chlorobenzoate was used instead of dodecyl 3-amino-4-methoxybenzoate was used. The resulting crystals became out Ligroin recrystallized. Benzoylaceto-1-chloro-S-dodecyloxycarbonylanilide was obtained in 60% yield. M.p. 98 to 100 C.

Synthesis 3

Preparation of Benzoylchloraceto-2-methoxy-5-dodecyloxycarbonylanilide (Formula XX)

In a 500 ccm three-necked flask equipped with a stirrer and thermometer, 48.1 g (0.1 mol) Benzoylaceto-2-methoxy-5-dodecyloxycarbonylanilide dissolved in 250 ecm of chloroform with stirring. Under Maintaining an internal temperature of 5 to 10 C were 14.8 g (0.11 mol) of sulfuryl chloride added dropwise. After stirring for 3 hours at an internal temperature of 10 C, the chloroform became distilled off at low temperature under reduced pressure. After adding 400 ecm of acetonitrile and cooling, white crystals separated out. These were filtered off and converted from 300 ecm petroleum ether

809648/1850

ίο

crystallized. 37 g of benzoylchloraceto ^ -methoxy-S-dodecyloxycarbonylanilide were obtained in 72% yield. Mp. 74-75 ⁰ C.

Table 2 shows the melting points and the results of nitrogen analysis of some typical yellow couplers according to the invention.

Table 2

COCHCONH

COOR

X X R. - C ₈ Hi ₇ I.
Y Y M.p. "C N analysis found Ver - C10H21 3.40 binding H - C12H25 - OCHa 58 to 60 calculated 3.11 H - C14H29 -OCH ₃ 75 to 76 3.30 2.86 III .... H - C16H33 -OCH ₃ 75 to 76 3.09 2.76 IV .... H - Ci ₈ H ₃₇ -OCH ₃ 71 to 72 2.91 2.69 V .... H -C ₈ H ₁₇ -OCH ₃ 77 to 79 2.75 2.59 VI .... H - C10H21 - OCH ₃ 80 to 82 2.61 3.11 VII .... H - C12H25 -Cl 94 to 95 2.48 2.91 VIII .... H - CH ₂ CH (C ₂ H ₅ ) (CHiJ) ₃ CH ₃ -CI 97 to 98 3.26 2.59 XI .... H - (CHa) ₇ CH (CHa) ₂ -Cl 98 to 100 3.06 3.26 XII .... H -CHaCiCHa) ₂ (CHa) ₇ CHs -Cl 71 to 73 2.89 2.93 XIII .... H - (CHa) ₂ O (CH ₂ ) OO (CHa) ₃ CH ₃ OCH ₃ -Cl 60 to 62 3.26 3.02 XIV .... H - C12H25 -Cl 85 to 86 3.06 2.93 XV .... H -CI 73 to 75 2.89 2.73 XVI .... Cl -Cl 74 to 75 3.06 XIX .... 2.71 XX ....

example 1

In a mixture of 1.2 ecm dibutyl phthalate, 3.0 ecm ethyl acetate and 0.8 ecm isopropanol, 4.0 g of coupler V and 0.8 g of a vinylpyrolidone-vinyl acetate copolymer (molar ratio 7: 3) were dissolved with heating. The solution was placed in 10 ecm of a 10% strength aqueous gelatin solution which contained 2.0 ecm of a 10% strength aqueous solution of sodium alkylbenzenesulfonate. This mixture was converted ^{into an emulsified dispersion of coupler, polymer and gelatin at 40 to 50 °} C. five times for 3 minutes each time, with pauses of 1 minute each time, in a high-speed homogenizer.

The entire dispersion became a halosilver gelatin emulsion mixed in, which contained 4.5 g of silver bromide and 7.5 g of gelatin. This mixture was used to produce a color photographic material cast on a cellulose acetate film support and dried. After exposure, a Solution of the following composition developed:

4-N, N-diethylaminoaniline 2.0 g

Sodium sulfite (anhydrous) 5.0 g

Sodium carbonate monohydrate 20.0 g

Potassium bromide 2.0 g

Water to top up to 11

After development, it was treated with the bleaching and fixing solutions described below and dried.

Bleach solution

Potassium ferric yanide 100 g

Potassium bromide 20 g

Water to top up to 11

Fixing solution

Na ₂ S ₂ O ₃ -SH ₂ 0 200 g

Sodium silicate 20 g

Acetic acid (28%) 45 g

Boric acid 7.5 g

Potassium alum 20 g

Water to top up to 11

The film produced in this way had a lemon yellow color and showed that in FIG. 1 absorption spectrum shown with an extremely low absorption in the green area. The yellow image was stable to heat and moisture, and the film was extremely transparent.

Example 2

With otherwise the same procedure as in Example 1, using coupler XIII was a Film made. The light yellow colored film had that shown in FIG. Spectral absorption curve shown in FIG with greatly reduced absorption in the green area.

This yellow image was also stable to light, heat and moisture and remained after a long storage time unchanged.

Example 3

A mixture of 2 g of Coupler V and 4 g of dibutyl phthalate was heated. The solution was mixed with 30 cc of a 7 ⁽⁾ / o gelatin solution containing 0.1 g of sodium dodecylbenzenesulfonate. The mixture was emulsified in a high speed homogenizer for ¹ minutes at 60 O ⁿ C. The entire emulsion was mixed into 100 g of a photographic emulsion containing 5 g of silver bromide and 6 g of gelatin. The mix was

poured onto a film support and dried. After exposure, the following solution was developed:

2-methyl-4-N, N-diethylaminoaniline 2.0 g

Sodium sulfite (anhydrous) 5.0 g

Sodium carbonate monohydrate 20.0 g

Potassium bromide ■ .... 2.0 g

Water to fill up on Il

The developed film was treated with the bleaching and fixing solutions given in Example 1 and then dried. A visually advantageous light yellow coloration with a slight red cast was obtained. The spectral absorption curve is in FIG. 3 shown. The yellow image was resistant to heat and moisture.

In comparative experiments with a yellow image produced by a known yellow coupler the fading from exposure to heat and moisture was noted. The results show the following Tabel:

Fade at 60C and 75% relative humidity

Coupler Initial
optical
Density Density according to
5 days Ver
pale Compound V ....
3.5 dicarboxy
((4-stearoylmono-
arnid) benzoyl) -
acetoanilide 1.20
1.35 1.15
0.40 4%
70%

40

35

Example 4

A mixture of 2 g of coupler V, 6 ecm 1 η-sodium hydroxide solution and 16 ecm methanol were used for Solution warmed. A 5% solution was obtained by making up to 40 ecm with water. The whole The solution was mixed into 100 g of a photographic emulsion containing 5 g of silver bromide and 6 g of gelatin. It was then neutralized with 1 ecm of 2% citric acid. After pouring onto a film carrier and drying, the film was treated as in Example 3. A light yellow image was obtained with an absorption maximum at 448 ma.

Example 5

2 g of coupler XIII were dissolved in 6 g of dibutyl phthalate with heating. The further processing was carried out as in Example 3. A yellow-colored film and its spectral absorption curve were obtained in Fig. 4 is shown. The visually advantageous shade of yellow was slightly reddish. The yellow picture was Resistant to light, heat and moisture and can be stored for a long time.

There have been attempts to determine the fading on exposure to light, heat and Moisture carried out. For comparison, yellow images were used that were obtained by means of a known Coupler were made. The results are shown in the following tables:

Fading when exposed to light
Irradiation with 1.5 kW xenon lamp (6500 K)

Coupler Initial
optical
Yellow density Density according to
5 hours Ver
pale Compound XIII ..
3,5 dicarboxy
((4-stearoylmono-
amide) benzoyl) -
acetoanilide 1.ΙΟ
Ι.05 1.01
0.68 8th%
35%

Fade at 60 C and 75% relative humidity

Coupler Initial
optical
Yellow density Density according to
5 days Ver
pale ²⁰ Compound XIII ..
3,5 dicarboxy
((4-stearoylmono-
amide) benzoyl) -
25 acetoanilide 1.15
1.35 1.15
0.40 0 »/ ..
70%

Example 6

2 g of coupler XIV (melting point 71 to 73 C) were heated to melt and in 30 ecm a 10% gelatin solution containing 0.2 g of sodium dodecylbenzenesulfonate, mixed in. The mixture was emulsified into one for 10 minutes at 85 ° C in a high speed homogenizer Dispersion transferred.

The entire dispersion was mixed into 100 g of a photographic emulsion, the 5 g of silver bromide and contained 6 g gelatin. This produced a film which, as in Example 3, exposed and developed became. A light yellow image with an absorption maximum at 445 ma was obtained.

Example 7

2 g of coupler XIV were dissolved in 4 ecm of ethyl acetate with heating. After adding 30 ecm a 7% gelatin solution containing 0.1 g of sodium dodecylbenzenesulfonate was in a Homogenizer produced an emulsified dispersion at 50 ° C. for 10 minutes. With this was A film was produced as in Example 6, which was exposed and developed as in Example 3. One received a light yellow image with an absorption maximum at 445 ma.

Example 8

As in Example 7, an image was made with Coupler XX. The light yellow picture had the absorption maximum at 443 ma.

Example 9

2 g of coupler XX were dissolved in 6 g of dibutyl phthalate with heating. The further processing took place as in Example 3. A light yellow image was obtained, the absorption maximum of which was 448 ma.

Claims (9)

Patent claims: 1.Color photographic recording material, which is in a silver halide layer as a yellow coupler contains a benzoylacetanilide with a substituent in the 5-position in the anilide nucleus, characterized in that the yellow coupler is an ester of m- (benzoylacetamino) benzoic acid with the general formula COOR IO is. in which R is an unbranched or branched alkyl group with at least 8 carbon atoms or an aliphatic radical with at least 8 carbon atoms and at least one ether bond. Y is a hydrogen atom, a lower alkoxy group or a halogen atom and X a hydrogen or halogen atom means. 2. Color photographic recording material according to claim 1, characterized in that the yellow coupler benzoylaceto-Z-methoxy-S-dodecyloxycarbonylanilide is. 3. Color photographic recording material according to claim 1, characterized in that the yellow coupler benzoylaceto-I-methoxy-S-tetradecyloxycarbonylanilide is. 4. Color photographic recording material according to claim 1, characterized in that the yellow coupler benzoylaceto ^ -methoxy-S-hexadecyloxycarbonylanilide is. 5. Color photographic recording material according to claim 1, characterized in that the yellow coupler benzoylaceto-I-chloro-S-dodecyloxycarbonylanilide is. 6. Color photographic recording material according to claim 1, characterized in that the yellow coupler is benzoylaceto-2-chloro-5- (2-ethylhexyloxycarbonyl) anilide. 7. Color photographic recording material according to claim 1, characterized in that the yellow coupler benzoylaceto-2-chk> r-5- (8,8-dimethyloctyloxycarbonyO-anilide is. 8. Color photographic recording material according to claim 1, characterized in that the yellow coupler benzoylaceto-2-chloro-5- (2,2-dimethyldecyloxycarbonyl) anilide is. 9. Color photographic recording material according to claim 1, characterized in that the yellow coupler benzoylchloraceto-2-methoxy-5-dodecyloxycarbonylanilide is. 1 sheet of drawings