US3770446A

US3770446A - Color photographic silver halide material containing acetanilide couplers

Info

Publication number: US3770446A
Application number: US00203882A
Authority: US
Inventors: M Furuya; T Endo; S Sato; T Hanzawa; I Inoue
Original assignee: Konica Minolta Inc
Current assignee: Konica Minolta Inc
Priority date: 1970-12-18
Filing date: 1971-12-01
Publication date: 1973-11-06
Anticipated expiration: 1990-11-06
Also published as: DE2162899B2; GB1346952A; DE2162899C3; JPS4917734B1; DE2162899A1

Abstract

WHEREIN Ar and Ar1 are an aryl group and X is hydrogen or a group capable of being released at the time of color development, is produced which is high in coupling reactivity, have spectral absorption characteristics suitable for the color reproduction principle of the tricolor substractive color photography and form dye images which are stable to heat, light and humidity.

A yellow coupler of the general formula:

Description

United States Patent 1 Sato et al.

[73] Assignee: Konishiroku Photo Industry Co.,

Ltd., Tokyo, Japan [22] Filed: Dec. 1, 1971 [21] Appl. No.: 203,882

[30] Foreign Application Priority Data Dec. 18, 1970 Japan 45/113101 [52] US. Cl 96/100, 96/3, 96/55, 260/562 [51] Int. Cl G031: 1/40 [58,] Field of Search 96/100 [56] References Cited UNITED STATES PATENTS 3,277,155 10/1966 Loria et al. 96/100 1 Nov. 6, 1973 Weissberger et a1. 96/100 lwama et al. 96/100 Primary Examiner-J. Travis Brown Att0rneyJordan B. Bierman et al.

[57] ABSTRACT A yellow coupler of the general formula:

CH X

wherein Ar and Ar are an aryl group and X is hydrogen or a group capable of being released at the time of color development, is produced which is high in coupling reactivity, have spectral absorption characteristics suitable for the color reproduction principle of the tricolor substractive color photography and form dye images which are stable to heat, light and humidity.

4 Claims, No Drawings COLOR PHOTOGRAPIIIC SILVER IIALIDE MATERIAL CONTAINING ACETANILIDE COUPLERS This invention relates to a color photographic material containing a novel yellow color-forming coupler.

It is well known to form a yellow, magenta and cyan colored image in a multi-layered color photographic material by coupling the couplers contained in the photographic material with the oxidation product of an aromatic primary amine type developing agent.

Couplers used for forming color photographic images should satisfy the following fundamental requirements:

1. They should be high in coupling reactivity with the oxidation product of a developing agent and should form' dy'e images high in color density.

2. They should form dye images which have spectral absorption characteristics suitable for the color reproduction principle of the tricolor substractive color photography.

3. They should form dye images which are stable to heat, light and humidity and are difficulty discolored.

In addi'tion thereto, the couplers are required to be such that they are easily dispersible in photographic emulsions and do not fog photographic emulsions or deteriorate the photographic speeds thereof.

In order to satisfy the above-mentioned requirements, many studies have heretofore. been made, but no satisfactory couplers have been obtained yet. Particularly in the case of yellow couplers, the fulfilment of the said three requirements is difficult. For example, the anisoylacetic acid anilide coupler disclosed in J apenese Patent Publication No. 19,956/1970, which has the structural formula (I) shown below, forms a yellow dye image high in'color density, but the dye image is insufficient in spectral absorption characteristics and light fastness.

' tCsHll Further, the yellow coupler disclosed in US. Pat. No.

tographic materials is particularly required. When used in such photographic materials, however, the conventional yellow couplers bring about various drawbacks. Accordingly, there has been desired the advent of yellow couplers suitable for quick photographic treatment.

With an aim to overcome the above-mentioned drawbacks, we made extensive studies to find that a color photographic material containing a novel yellow coupler of the general formula shown below not only exhibits improfye d photographic speed and dye image density but also gives a dye image having excellent fastness and light absorption characteristics advantageous for color reproduction, and that a marked enhancement in dye image density can be attained particularly when one-bath bleaching-fixing method'is adopted during the color development of the photographic material. General formula:

idirnethylphenyl or 4-chloro iidimethylphenyl, while;

Ar, which is aryl group used in a yellow dye imagefonning acylacetoanilidetype coupler of the prior art,

represents, for example, phenyl, 3,5-dicarboxyphenyl, 2'chloro-5-[y-(2,4-di-tert-amylphenoxy)butyramido]- phenyl, 2-methoxy-4-[a-(2,4-di-tert-amylphenox- C5Hu(t) y)acetamido]phenyl, 2- hl 5-[i 3- 3,265,506, which has the structural formula (II) shown 45 dodecyloxyphenoxy)butyramido]phenyl, 2-chloro-5- below, gives a ye llowdye image less in absorption at the green light wavelength region, which is undesirable for color reproduction according to the substractive photography, and excellent instability to light and (N-methyl-N-octadecylsulfamyl)phenyl, 2-methoxy-5- dodecylsuccinimidophenyl or 2-chloro-5-hexadecyloxycarbonylphenyl; and X is hydrogen or'a group capable of being released at the time of color development and heat, but has such drawbacks 'that it is low in coupling 50 represents, for example a chloro, bromo, acetoxy, steareactivity with the oxidation producto'f a developing agent and hence difficulty forms a dye image high in density.

CPI; mc d 0ocH,coNH

t i n Thus, among theconventional couplers, those capable of forming high density dye images cannot give dye images excellent in light and moisture fastness, while those capable of forming dye images excellent in light and moisture fastness cannot give high density dye im- 5 roxy, phenylthio, 4-carboxyphen'oxy, methylsulfonyloxy or benzotriazole group. e

The coupler of the aforesaid general'forinula displays excellent effects which cannot be expected from the conventional couplers, as mentioned previously. These excellent effects are considered ascribable to the aryloxy group introduced into the a-position of the isobutyryl group shown in the aforesaid formula. That is, a color photographic material containing a coupler of the aforesaid general formula, in which an alkyl, aryl or alkoxy group has been introduced into the a-position of said isobutyryl group, is poor in linearity of the characteristic curve thereof and hence gives a dye image low in gradation. Further, particularly when one-bath bleaching-fixing method is adopted for the development of such color photographic material, the density of the resulting color image and other photographic properties are not satisfactory. However, when the cou- 5 pler of the aforesaid general formula is used, no such drawbacks are brought about as will be clarified' in the examples set forth later.

The coupler of the aforesaid general formula which CH: Q-o-i-o ocmc ONHQ is used in the present invention is synthesized, for ex ample, in the following manner:

a-( a-Phenoxyisobutyrl )-2-chloro-S-[-y-(2,4-di-tertamylphenoxy )butyramido]acetanilide W oi An a-halogeno-isobutyric acid ethyl ester is reacted with a substituted or unsubstituted phenol in the pres- 30 ence of sodium alcoholate to form. an a-aryloxyisobutyric acid ester. The thus formed ester is treated with sodium acetonitrile to prepare an aryloxyisobutyryl acetonitrile, which is then imino-etherified and hydrolyzed to obtain an aryloxy-isobutyrylacetic acid es- 35 ter. This ester may alternatively be synthesized by condensing an acetoacetic acid ester with an aryloxyisobutyric acid chloride, and hydrolyzing the condensation product. The thus obtained acetic acid ester is condensed with a correspondingarylamine to obtain a coupler of the aforesaid general formula in which X is hydrogen. A coupler of the aforesaid formula, in which CH a o-i-cocmcom1 tiHn a-[ a-(4-Methoxyphenoxy)iSobutyrylj Z-chlOro-S-[y- 2,4-di-tert-amylphenoxy)butyramido]acetanilide CH3 mco--o-c cocmcomr II-Ia I oocmcoocfluu a-[a-(4-Methoxyphenoxy)isobutyryl]-2-chloro-5- dodecyloxycarbonyl-methoxycarbonyl acetanilide c1 CH3 Hao--o-e-coomcoml (L CH3.

4 OzN ClBHN a-[a-(4-Methylphenoxy)isobutyryl]2-chloro-5-(N- methyl-N-octadecylaminosulfonyl) acetanilide 3 ILLICOwHmOQ-wiHH tu n a-[a-( 2-Chlorophenoxy)isobutyryl]-2-chloro-5-['y- (2,4-di-tert-amylphenoxy)butyrylamido] acetanilide nncowmnoQ-rmm 7 a-(4-carboxyphenyoxy )-a-[a-( 4-methoxyphenoxy) isobutyryl]-2-chl0ro-5-['y-( 2,4-di-tertamylphenoxy)butyramido] acetanilide on; C1O+CO err-com;

cm (i) c 0 Cum,

oz-Lauryloxy-a-[a-(4-chlorophenoxy)isobutyryl]-3,5-

dicarboxy acetanilide Among the above-exemplified couplers, the couplers of the type exemplified by the numbers (l2), (l3) and (14) are those which have been called two-equivalent couplers by those skilled in the art. In forming 1 mole of yellow dye, an ordinary coupler requires 4 moles of silver halide, whereas the two-equivalent coupler requires only 2 moles of silver halide. Thus, the coupler of the two-equivalent type requires a smaller amount of silver halide in forming a definite amount of dye, and hence brings about many such advantages in preparing a color photographic material as saving of silver, thinning of emulsion film, improvement in sharpness, etc. Further, the coupler of the type exemplified by the number is a coupler for use in a light-sensitive material to be developed according to dye image transfer method, i.e., a coupler suitable for use in a lightsensitive material to be color-developed according to a method in which the diffusibility of a dye formed in the light-sensitive layer of the photographic material is utilized, and the dye'is diffused and transferred to the image-receiving layer adjacent to the light-sensitive layer, thereby forming a dye image in the image-receiving lay- Concrete procedures for synthesizing the exemplified couplers are set forth below with reference to synthesis examples.

Synthesis Example 1 a. A solution of 23 g. of metallic sodium in 1 liter of distilled alcohol was charged with 94 g. of phenol and then boiled for 30 minutes. Thereafter, 195 g. of

a-bromoisobutyric acid ethyl ester was added, and the resulting mixture was boiled for 3 hours. Subsequently,

T LE

X CH:

X b.p. (C/mrnHg) n ss-9o/a 4-ocn, iso-lsa/a 44:11, 104-10555 107-1 12/2.s 44:1 1 13-1 15/2 2,40 126-128/2.5 35-011,] 129-130/3 44:1

s-no 155-160/3 the liquid reaction mixture was poured into water, and

b. 115 Grams of metallic sodium was dissolved in 250 ml. of methanol and then the methanol was distilled off under reduced pressure. The residue was suspended in 300 ml. of acetonitrile, added with 100 g. of the a-phenoxyisobutyric acid ethyl ester obtained in (a) and then boiled for 5 hours. Subsequently, the liquid reaction mixture was poured into water, and unreacted ester was extracted with 300 ml. of ether. Thereafter, the aqueous layer was adjusted to pH 6.0, and a deposited oily substance was extracted with ether, washed with water, dried and then freed from the other under reduced pressure. The residue was recrystallized from 100 ml. of ligroin to obtain white powdery a-phenoxyisobutyl acetonitrile, m.p. 7374C., yield 42%. Nitrile compounds different in substituent can be syn= thesized in the same manner as above by use of the' a-substituted phenoxyisobutyric' acid ethyl ester obtained in (a). Typical examples of the nitrile compounds are set forth in Table 2.

TABLE 2 x CH;

X m.p. (refractive index in the case of liquid) H 7374C. 4-OCH; 84-86C. 44:", 71c. 2-Cl Liquid, 01,, 1.5082 4-Cl 8182C. 2,4-Cl Liquid, n 1.5223 3,5-CH Liquid, n ,f 1.5423 4-Cl c. 35 Grams of the a-phenoxylsobutryhacetonitri'le obtained in (b) was dissolved in a mixed solvent comprising 24 g. of absolute alcohol and- 32 g. of chloroform. Into the resulting solution, hydrochloric acid gas was introduced for 2 hours at 40 to 45C. Subsequently, the liquid reaction mixture was poured into water and heated at 50 to 55C. for 30 minutes to deposit an oily substance. The oily substance was extracted with n-hexane, washed with water, dried and then concentrated under reduced pressure to obtain a-phenoxyisobutyrylacetic acid ethyl ester, yield percent. In the same manner as above, )S-keto-acid esters were obtained by use of the substituted a-phenoxyisobutyryl-acetonitrile synthesized in (b). Typical examples of the esters are set forth in Table 3.

TABLE 3 CH: 7 Q-o-(LcocWmo 01111 X (iHa X Refractive index H n 1.4920 4-OCH n 1.5010 4-CH, n 1.5020 2-Cl m, 1.5093 4-Cl u 1.5076 2,4-Cl 01,, 1.5223 3,5-CH n 1.5350 4-Cl d. 44 Grams of 2-chl0ro-5-(y-2,4-di-tert-aminophenoxy-butyramido) aniline was dissolved at an elevated temperature in 220 ml. of xylene. The resultingsolution was added with 27 g. of the a-phenoxy-isobutyryl-acetic acid ethyl ester obtained in (c), boiled,

freed by distillation from formed alcohol and then boiled for 3 hours. Thereafter, the xylene was removed by distillation under reduced pressure, and the residual glutinous substance was heated and dissolved in hexane and then allowed to cool, whereby the glutinous substance solidified. The thus obtained solid was recov-- ered by filtration, dried and then recrystallized from methanol to obtain a white powder, m.p. 130-131C., yield 65%. This powder was the exemplified coupler (1). In the same manner as above, the exemplified cou- 9 and were obtained by the condensation of amines with the B-keto-acid esters different in substituent which were obtained in (c).

TABLE 4 ,Properties of synthesized couplers Nitrogen analysis Exemplified 75 Grams of the a-(3-nitrophenoxy)isobutyric acid ester-synthesized in (a) of Synthesis Example 1 was heated at 60C. for 10 minutes together with 375 ml. of alcohol and 190 ml. of percent caustic soda. Thereafter, the reaction mixture w as poured into water and acidified with hydrochloric acid to deposit a pale yellow precipitate. This precipitate was recovered by filtration and recrystallized from methanol to obtain a-(3-nitrophenoxy)isobutyric acid, m.p. 45-50C. This acid was treated with phosphorus pentachloride in chloroform to form an acid chloride, which was then reacted with an ethoxymagnesium salt of acetoacetic acid ethyl ester to synthesize a-(3-nitrophenoxy) isobutyrylacetic acid ethyl ester (n,, 1.5150). This ester was condensed with anilinein xylene to a-[a-3- nitrophenoxy) isobutyryl1acetanilide (m.p. l 15C.), which was then converted into a-[a-(S-aminophenoxy) isobutyry1]acetanilide (m.p. 103104C.) and thereafter condensed with lauric acid chloride in acetonitrile to synthesize the exemplified coupler (9), m.p. 95-97C.

Nitrogen analysis:

Calculated 5.66%; Found 5.82%

SYNTHESIS EXAMPLE 3 comprising acetonitrile and triethylamine, charged 5 with 0.3 g. of thiophenol and then boiled. Subsequently, the solvent was removed by distillation under TABLE 5 Properties of couplers Nitrogen analysis Exemplified m.p. v

coupler (C. Calculated Found (12) -78 3.92 3.90 (13) 63-65 3.63 3.55 (14) ll3-ll5 3.43 3.32

SYNTHESIS EXAMPLE 4 -A solution of 50 g. of aminoisophthalic acid dimethyl ester in 200 ml. of xylene was charged with 70 g. of the a-(4-chlorophenoxy)isobutyrylacetic acid ethyl ester obtained in (c) of Synthesis Example 1 and then boiled, and formed alcohol was distilled off. Thereafter, the xylene was removed by distillationunder reduced pres- Sure, and the residue was dissolved in alcohol, charged with 100 ml. of 20 percent caustic soda, kept at 60C. for 10 minutes, diluted with water and then acidified with hydrochloric acid to deposit a precipitate. The precipitate was recovered by filtration, dried and then recrystallized from methanol to obtain a-[a-(4- chlorophenoxy)isobutyryl]-3,S-dicarboxyacetanilide, m.p. l-188C., yield 60 percent. This acetanilide was treated with sulfuryl chloride in chloroform to form a-chloro-a-[a-(4-chlorophenoxy)isobutyryl]-3,5- dicarboxyacetanilide, which was then condensed with sodium stearate in acetonitrile to obtain the exemplified coupler (15 m.p. 85-88C.

Nitrogen analysis:

Calculated 2.08% Found 2.04%

For incorporation of the aforesaid couplers used in the present invention into color photographic materials, there may be adopted any of the known procedures. For example, in the case of a coupler of the type exemplified by the number l i.e. a coupler having no hydrophilic group in the molecule, a color photographic material may be prepared accordingto the socalled protect type dispersion procedure carried out by dissolving the coupler in a high boiling solvent such as dibutyl phthalate or tricresyl phosphate or a low boiling solvent such as ethyl acetate or butyl acetate, or in a mixture thereof, mixing the resulting solution with an aqueous gelatin solution containing a surface active agent, dispersing the mixed solution by means of a col loid mill or a high speed rotary mixer to form a coupler dispersion, adding the coupler dispersion directly to a silver halide photographic emulsion, coating the emulsion on a suitable support such as a glass plate, synthetic resin sheet, cellulose triacetate film, polyester film, baryta paper or laminated paper, and then drying the emulsion. In the case of a coupler of the type exemplified by the number (15), i.e. a coupler having a hydrophilic group in the molecule, a color photographic material may be prepared according to the so-called Fischers method carried out by dissolving the coupler in an aqeuous caustic alkali oralkali carbonate solution, either alone or in combination with a hydrophilic organic solvent, adding the resulting solution directly to a silver halide photographic emulsion, coating the emulsion to such a support as mentioned above, and then drying the emulsion.

The above-mentioned procedures are illustrative and not limitative. 1n the above, the amount of the coupler to be incorporated into the emulsion is preferably in' the range from to 100 g. per mole of silver halide, but is not always limited to said range and is variable according to the kind of the coupler and the application purpose of the resulting color photographic material. Further, the coupler may be used in combination with a coupler of same or different kind in order to improve the dispersibility thereof into the photographic emulsion and to satisfy such conditions as the variation and control of hue which are necessary for preparation and properties of color photographic material.

The silver halide photographic silver halide emulsions used in the present invention may be prepared by use of various silver halides such as silver chloride, silver iodobromide and silver chlorobromide. These emulsions may contain chemical sensitizers, e.g., sulfur sensitizers, such natural sensitizer as present in gelatin, reduction sensitizers and noble metal salts. Further, the emulsions may have been incorporated with ordinary photographic additives such as, for example, antifoggants, stabilizers, anti-stain agents, anti-irradiation agents, physical property-improving high polymer additives, hardeners and coating aids, and may contain known carbocyanine dye, merocyanine dye, etc. as optical sensitizers therefor.

The thus obtained color photographic materials are exposed to a-rays, B-rays or the like radiations, visible rays or infrared rays, developed with a developer containing a p-phenylenediamine type developing agent, and then bleached, desilvered and fixed, whereby high density dye images excellent in spectral absorption characteristics, light fastness and moisture fastness and high in gradation can be obtained.

When an ultraviolet absorber of the benzophenone type (e.g., 2-hydroxy-4-dodecyloxybenzophenone) or of the triazole type (e.g. 2-(2-hydroxy-3', 5-di-tert-butylphenyl)benzotriazole) is incorporated into a color photographic material containing the coupler of the aforesaid general formula, the light fastness of the resulting color image canfurther be enhanced. It is also possible to further enhance the light fastness by use of said ultraviolet absorber in combination with an alkyl-substituted phenol.

Typical developing agents used for development of the color photographic materials according to the present invention are sulfates sulfites and hydrochlorides of:

N,N-diethyl-p-phenylenediamine,

N-ethy1-N-B-methanesulfonamidoethyl-3-methyl-4- aminoaniline,

N-ethyl-N-hydroxyethyl-p-phenylenediamine,

N-ethyl-N-hydroxyethyI-Z-methyl-pphenylenediamine, and

N,N-diethy1-2-methy1-p-pheny1enediamine.

Further, the colordevelopers may contain development-controlling agents, e.g. citrazinic acid, in addition to the above-mentioned developing agents.

The present invention is illustrated in further detail below with reference to examples, but the examples are merely illustrative and the invention is, of course, not limited only to these.

Example 1 20 Grams of each of the exemplified couplers l and (8) was dissolved at 60C. in a mixed solvent comprising 20 ml. of dibutyl phthalate and 60 ml. of butyl acetate. The resulting solution was mixed with 10 m1. of a 10 percent aqueous solution of alkanol B (alkyl-naphthalenesulfonate produced by Du Font) and 200 ml. of a 5 percent aqueous gelatin solution, and the mixed so solution was dispersed by means of a colloid mill to form a coupler dispersion. This coupler dispersion was added to 1 kg. of a gelatin silver iodobromide emulsion, which was then coated on a film base and dried to obtain a color photographic material 'having a stable film free from the fear of deposition of Sodium hydroxide Water to make vH'H PPE" mocmoo omma The developed photographic materials were subjected to ordinary stopping and fixing treatments, washed with water for 10 to 15 minutes, and then bleached at 25C. for 5 minutes in a bleaching bath of the following composition:

Potassium ferricyanide Potassium bromide 50 g. Water to make 1,000 ml.

The bleached photographic materials were further washed with water for 5 minutes, and then treated at 25C. for 5 minutes in a fixing bath of the following composition:

Sodium thiosulfate (pentahydrate) 250 g. Water to make 1,000 ml.

Photographic properties Moisture Relative speed Latitude D max. Amax (mu) AA (mp.) l,igh1 faslncss fnstncss Known coupler (1) 150 0.76 1.94 445 81 77 )8 Known coupler (ll) 100 1.0 1.20 447 67 96 99 Exemplified coupler (1).. 116 1.18 1.32 445 94 99 Exemplified coupler (8) I 110 1.15 1.27 445 66 95 99 In Table 6, the latitude is the difference between the optical density 1.4 on the characteristic curve of the color photographic material and the amount of exposure corresponding to 0.3, and is represented by a relative value based on the difference in the case of the known coupler (II); the AA is the value (unit mg.) of difference between the absorption wavelength corresponding to the optical density 0.2 on the characteristic curve of the photographic material and the absorption maximum wavelength ()tmax), when the optical density of the absorption maximum wavelength is deemed as 1.0; the light fastness is the ratio of residual density to initial density when a sample having an initial density of 1.0 was exposed to an arc lamp for 16 hours; and the moisture fastness is the ratio of residual density to initial density when a sample having an initial density was allowed to stand for 14 days in an atmosphere at 50C. and 80 percent relative humidity.

From Table 6, it is understood that the color photographic material according to the present invention is more improved than the photographicmaterial containingthe known coupler (II) in photographic speed and maximum color density of dye image and is higher in gradation to bring about marked advantages in the reproduction of color, and that the color photographic material of the present invention gives a dye image far more excellent in spectral characteristics and fastnessesthan that formed by the photographic material containing the known coupler (1).

Example 2 Using 20 g. of eachof the exemplified couplers (l) and (5) and the known coupler (II), a coupler dispersion was prepared in the same manner as in Example 1. This dispersion was added to 1 kg. of a silver chlorobromide emulsion, which was then coated on a baryta paper and dried to obtain a'color photographic material.

The thus obtained photographic materials were exposed according to an ordinary procedure, developed at 25C. for l0 minutes with ,the same developer as in Example 1 and then treated at 25C. for 4 minutes in a stopping-fixing bath of the following composition:

Ammonium thiosulfate 120 g. Potassium metabisulfite 20 g. Acetic acid ml. Water to make 1,000 ml.

tetraacetic acid 40 g. Ferric chloride 30 g. Sodium carbonate (monohydrate) g. Potassium bromide g.' Sodium thios'ulfate (pentahydrate) 200 g. Water to make 1,000 ml.

The thus treated photographic materials were washed with water for 10 minutes, immersed for 2 minutes in a stabilization bath and then dried.

The absorption maximum and maximum color density of each of the thus obtained dye images were as set forth in Table 7.

TABLE 7 Amax (mu) D max Known coupler (ll) 447 1.16 Exemplified coupler (1 445 1 .86 447 1.79

Exemplified coupler (5) From Table 7, it is understood that the maximum density of yellow dye image formed from the coupler used in the present invention is far more excellent than in the case of the known coupler. Further, when Table 7 is compared with Table 6 in Example 1, it is understood that even when a single bleaching-fixing bath'is used according to Example 2, the coupler used in the present invention is excellent 'in color image-forming ability.

Example 3 A solution of the exemplified coupler (15) in an aqueous lN-caustic potash solution was added to a gelatin silver iodobromide emulsion. After adjusting to pH 6.5, the emulsion was coated on a film base and then dried to prepare a color photographic material. After exposure, the photographic material was contacted with a mordant-incorporated image-receiving sheet, which had previously been impregnated with a develaqueous sodium hydroxide solution.

After the development, the film was peeled off from the image-receiving sheet, whereby'a mordant-loaded yellow dye image was transferred onto said sheet. This dye image was not only excellent in light fastness and moisture fastness, like the images obtained in other examples, but also had a sufficient density and was high in gradation.

What we claim is: v

1. A light-sensitive silver halide color photographic material which comprises a support and coated thereon a light-sensitive silver halide emulsion layer, characterized in that a yellow coupler of the general formula 3 Ar O CC-O -CH CONH-Ar' CH X wherein Ar and A1" are individually an aryl group; and X is hydrogen, chlorine, bromine, acetoxy, lauryloxy, stearoxy, phenylthio, 4-carboxy phenoxy, methylsulfonyloxy or benzotriazole is located in said material.

2. The photographic material asclaime'd in claim '1', whereinsaid yellow coupler is incorporated inthe lightsensitive 'silver halide emulsion layer.

3. The phtographic material as claimed in claim 1, wherein Ar and Ar, or Ar and Ar are independently phenyl or naphthyl. v

4. The light-sensitive silver halide color photographic material as claimed in claim 1, wherein said coupler is selcted from the group consisting of g a-(a-Phenoxyisobutyryl)-2-chloro-5-[-y-(2,4-di-tertamylphenoxy)butyramido1acetanilide, oz-[a-(4-Methoxyphenoxy)isobutyryl]-2-chloro-5-['y- (2,4-di-tert-amylphenoxy)butyramidolacetanilide, a-[a-(4-Methoxyphenoxy)isobutyryl]-2-chloro-5- dodecyloxycarbonyl-methoxycarbonyl acetanilide, a-[a-(4-Methylphenoxy)isobutyryl] 2-chloro-5-(N- methyl-N-octadecylaminosulfonyl) acetanilide,

Claims

2. The photographic material as claimed in claim 1, wherein said yellow coupler is incorporated in the light-sensitive silver halide emulsion layer.
3. The phtographic material as claimed in claim 1, wherein Ar and Ar'', or Ar and Ar'' are independently phenyl or naphthyl.
4. The light-sensitive silver halide color photographic material as claimed in claim 1, wherein said coupler is selcted from the group consisting of Alpha -( Alpha -Phenoxyisobutyryl)-2-chloro-5-( gamma -(2,4-di-tert-amylphenoxy)butyramido)acetanilide, Alpha -( Alpha -(4-Methoxyphenoxy)isobutyryl)-2-chloro-5-( gamma -(2,4-di-tert-amylphenoxy)butyramido)acetanilide, Alpha -( Alpha -(4-Methoxyphenoxy)isobutyryl)-2-chloro-5-dodecyloxycarbonyl-methoxycarbonyl acetanilide, Alpha -( Alpha -(4-Methylphenoxy)isobutyryl)-2-chloro-5-(N-methyl-N-octadecylaminosulfonyl) acetanilide, Alpha -( Alpha -(2-Chlorophenoxy)isobutyryl)-(2-chloro-5( gamma -(2,4-di-tert-amylphenoxy)butyrylamido)acetanilide, Alpha -( Alpha -(4-Chlorophenoxy)isobutyryl)-2-chloro-5-( gamma -(2,4-di-tert-amylphenoxy)butyramido)acetanilide, Alpha -( Alpha -(4-Chlorophenoxy)isobutyryl)-2-methoxy-5-dodecylsuccinimide acetanilide, Alpha -( Alpha -(4-Chlorophenoxy)isobutyryl)-2-chloro-5-hexadecyloxycarbonyl acetanilide, Alpha -( Alpha -(3-Laurylamidophenoxy)isobutyryl)benzoyl acetanilide, Alpha -( Alpha -(2,4-Dichlorophenoxy)isobutyryl)-2-chloro-5-( Alpha -(3-dodecyloxyphenoxy)butyramido)acetanilide, Alpha -( Alpha -(4-Chloro-3,5-dimethylphenoxy)isobutyryl)-2-chloro-5-( gamma -(2,4-di-tert-amylphenoxy)butyramido) acetanilide, Alpha -Chloro- Alpha -( Alpha -(4-methoxyphenoxy)isobutyryl)-2-chloro-5-( gamma -(2,4-di-tert-amylphenoxy)butyramido) acetanilide, Alpha -Phenylthio- Alpha -( Alpha -(4-methoxyphenoxy)isobutyryl)-2-chloro-5-( gamma -(2,4-di-tert-amylphenoxy)butyramido) acetanilide, Alpha -(4-Carboxyphenoxy)- Alpha -( Alpha -(4-methoxyphenoxy)isobutyryl) -2-chloro-5-( gamma -(2,4-di-tert-amylphenoxy)butyramido)acetanilide, and Alpha -Lauryloxy- Alpha -( Alpha -(4-chlorophenoxy)isobutyryl) 3,5-dicarboxy acetanilide.