US2950314A - Color couplers for color photography - Google Patents

Color couplers for color photography Download PDF

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US2950314A
US2950314A US575718A US57571856A US2950314A US 2950314 A US2950314 A US 2950314A US 575718 A US575718 A US 575718A US 57571856 A US57571856 A US 57571856A US 2950314 A US2950314 A US 2950314A
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amino
sulphofluoride
benzene
color
acetyl
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Cat Arthur Henri De
Raphael Karel Van Poucke
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Gevaert Photo Producten NV
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
    • C07K1/006—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length of peptides containing derivatised side chain amino acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/38—Nitrogen atoms
    • C07D277/44—Acylated amino or imino radicals
    • C07D277/46—Acylated amino or imino radicals by carboxylic acids, or sulfur or nitrogen analogues thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/54—Nitrogen and either oxygen or sulfur atoms
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
    • G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
    • G03C7/32—Colour coupling substances
    • G03C7/36—Couplers containing compounds with active methylene groups
    • G03C7/362—Benzoyl-acetanilide couplers

Definitions

  • the color couplers needed for this purpose are preferably incorporated in the photographic emulsion layers or in colloid layers located in the vicinity thereof.
  • a substituent such as a chain of several carbon atoms.
  • substituents which render the coupler water-soluble are usually introduced. Sulpho groups in particular are efiective in this respect.
  • acylacetarylides As couplers for yellow, the acylacetarylides have been used in practice. As acylacetarylides sulphonated in their arylide part, only the acetyl acetarylides have been obtained by allowing diketene to react with sulphonated aniline derivatives. Corresponding sulphonated aroylacetarylides have not been obtained, due to the lack of a suitable method.
  • An object of the present invention is a method for preparing aroyl-acetarylides sulphonated in the arylide part.
  • a further object is a class of new sulphonated aroyl-acetarylides.
  • Another object is a process for the production of a colored photographic image by the use of these aroyl-acetarylides.
  • Still a further object is a light-sensitive photographic material containing such aroylacetarylides.
  • a reducible silver salt image is developed with a primary amino aromatic developing agent in the presence of an aroyl-acetarylide sulphonated in its arylide part wherein the hydrogen atoms of the metehylene group may be replaced by substituents which readily split oil on color development.
  • such compounds are prepared by condensing an aroylacetic ester with a compound of the formula NH -aryl-SO F, and by hydrolyzing the rsulting sulphofluoride into the corresponding sulphonic acid or ester.
  • the aryl group of the ester or of the sulphofluoride may contain a group able to render the coupler fast to difiusion.
  • the aryl group of the ester may contain a nitro group which after condensation may be reduced to an amino group, wherein a group rendering fast to diffusion may be introduced Without difliculty.
  • Aromatic compounds may be treated with fluorosulphonic acid.
  • Steinkopf I. prakt. Chem. (2) 117 (1927) 1-82
  • Steinkopf has nitrated two sulphofluorides, obtained in this way, into m-Nitro-benzene sulphofluoride, and p-Methyl-m-nitro-benzene sulphofiuon'de.
  • nitro-sulphofluorides have been converted into the corresponding amino compounds by reducing a 25% alcoholic solution of the nitro-sulphofluoride by means of Raney nickel at 40-400 C. and under a hydrogen pressure of 10-100 atm. After elimination of the Raney nickel, the filtrate is either distilled or evaporated until the amine crystallizes. In this way we have prepared.
  • Potassium fluoride may also be allowed to react with acetyl-amino arylene sulphochlorides.
  • the resulting acetylamino-arylene-sulphofiuorides may be de-acylated by means of HCl in alcohol. In this way we have prepared:
  • CH CH (CH COCl (myristoyl-chloride), p-myristoyl-amino-m-nitro-benzenesulphofluoride, M.P. 64 C. (from acetonitrile), is obtained. Reducing the latter with Raney nickel in dioxane at 40-50 C. and under a hydrogen pressure ofi 10-50 atm., eliminating the nickel and evaporating the filtrate until the product crystallizes by cooling, yields p-myristoyl-amino-m-amino-benzene-sulphofluoride, M.P. 122 C.
  • Condensation of these sulphofluorides with beta-keto esters may be done in the usual way by refluxing the two compounds in toluene or xylene, evaporating the latter after condensation, and recrystallizing the product.
  • the sulphofluorides In order to convert the sulphofluorides into the correspending sulphonic acids, they are first dissolved in acetone or aqueous dioxane and treated at 60 C. with an aqueous solution of sodium hydroxide. After cooling, the sodium salt of the coupler crystallizes out, or is precipitated by the addition of salt. These sodium salts are recrystallized and may easily be. dissolved in water or in a mixture of water and alcohol for addition to a silver halide emulsion or to a colloid which will form a layer adjacent to a silver halide emulsion layer or separated therefrom by a water-permeable colloid layer.
  • primary aromatic amino developing agents may be used mono-, diand tri-amino compounds; as monoamino developers may be mentioned amino phenols and amino cresols, their halogen derivatives, and also amino naphthols.
  • R represents an aryl radical selected from the group consisting of alkoxyphenyl, alkoXy naphthyl, dialkoxy phenyl, dichloro alkoxy phenyl, isooctyl phenoxy ethoxy phenyl, nitrophenyl, and acylamino phenyl
  • R" represents a monocyclic arylene radical of the.
  • benzene series selected from the group consisting of phenylene, chlorophenylene, dialkyl amino phenylene, alkyl phenylene, alkoxy phenylene, dialkoxyphenylene, and acylaminophenylene, and Me represents an alkali metal atom, comprising condensing an 'aroyl acetic ester of the following formula:
  • R represents a lower alkyl group, with a compound of the formula H N-R'SO F, and hydrolyzing V the resulting compound in the presence of an alkali metal hydroxide.
  • R represents an aryl radical selected from the group consisting of alkoxyphenyl, alkoXy naphthyl, dialkoxy phenyl, dichloro alkoxy phenyl, isooctyl phenoxy ethoxy phenyl, nitrophenyl, and acylamino phenyl
  • R represents a monocyclic arylene radical of the benzene series, selected from the group consisting of phenylene, chlorophenylene, dialkyl amino phenylene, alkyl phenylene, alkoxy phenylene, dialkoxyphenylene, and acylaminophenylene
  • Me represents an alkali metal atom, said sulphonated aroyl acetarylide being prepared by condensing an aroyl acetic ester of the following formula:
  • RCO'CH -COOR wherein R" represents a lower alkyl group, with a compound of the formula H NR'-SO F, and hydrolyzing the resulting compound in the presence of an alkali metal hydroxide.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • Biophysics (AREA)
  • Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Analytical Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

llnited States Patent COLOR COUPLERS FOR COLOR PHOTOGRAPHY Arthur Henri De Cat, Mortsel-Antwerp, and Rapha'e'l Karel Van Poucke, Mechlin, Belgium, assignors to Gevaert Photo-Producten N.V., Mortsel, Belgium, 2 Belgian company No Drawing. Filed Apr. 3, 1956, Ser. No. 575,718 Claims priority, application Great Britain Apr. '5, 1955 2 Claims. (Cl. 260-507) This invention relates to a process for producing photographic color images by color development, to color couplers for use in such process, and to the preparation of such color couplers.
It is known to produce color photographic images by color development. The color couplers needed for this purpose are preferably incorporated in the photographic emulsion layers or in colloid layers located in the vicinity thereof. In order to prevent wandering of these conplers out of their initial layer into another layer, they are usually loaded by a substituent such as a chain of several carbon atoms. Besides this substituent, other substituents which render the coupler water-soluble are usually introduced. Sulpho groups in particular are efiective in this respect.
As couplers for yellow, the acylacetarylides have been used in practice. As acylacetarylides sulphonated in their arylide part, only the acetyl acetarylides have been obtained by allowing diketene to react with sulphonated aniline derivatives. Corresponding sulphonated aroylacetarylides have not been obtained, due to the lack of a suitable method.
An object of the present invention is a method for preparing aroyl-acetarylides sulphonated in the arylide part. A further object is a class of new sulphonated aroyl-acetarylides. Another object is a process for the production of a colored photographic image by the use of these aroyl-acetarylides. Still a further object is a light-sensitive photographic material containing such aroylacetarylides.
Now we have found a method for preparing such aroyl-acetarylides sulphonated in the arylide part and it has been found that such compounds are good couplers. In comparison with similar couplers, they are very soluble and are indifierent to silver halide emul- SIOIIS.
According to the present invention, a reducible silver salt image is developed with a primary amino aromatic developing agent in the presence of an aroyl-acetarylide sulphonated in its arylide part wherein the hydrogen atoms of the metehylene group may be replaced by substituents which readily split oil on color development.
Further according to the present invention, such compounds are prepared by condensing an aroylacetic ester with a compound of the formula NH -aryl-SO F, and by hydrolyzing the rsulting sulphofluoride into the corresponding sulphonic acid or ester. The aryl group of the ester or of the sulphofluoride may contain a group able to render the coupler fast to difiusion. Alternatively, the aryl group of the ester may contain a nitro group which after condensation may be reduced to an amino group, wherein a group rendering fast to diffusion may be introduced Without difliculty.
Compounds of the formula NH -aryl-SO F may be obtained in different Ways.
Aromatic compounds may be treated with fluorosulphonic acid. Steinkopf (I. prakt. Chem. (2) 117 (1927) 1-82) has nitrated two sulphofluorides, obtained in this way, into m-Nitro-benzene sulphofluoride, and p-Methyl-m-nitro-benzene sulphofiuon'de.
According to W. Davies and J. Dick (J. Chem. Soc. (1931) 2104-09), compounds of the formula aryl-S0 01 may be treated with potassium fluoride. have prepared:
o-Nitro-benzene-sulphofluoride, M.P. 60 C., p-Nitro-benzene-sulphofiuoride, M.P. C., p-Chloro-rn-nitro-benzene-sulphofluoride, M.P. 54 C.,
and
In this way we p Dimethylamino m nitro -benzene -sulphofluoride,
M.P. 64 C.
The above six nitro-sulphofluorides have been converted into the corresponding amino compounds by reducing a 25% alcoholic solution of the nitro-sulphofluoride by means of Raney nickel at 40-400 C. and under a hydrogen pressure of 10-100 atm. After elimination of the Raney nickel, the filtrate is either distilled or evaporated until the amine crystallizes. In this way we have prepared.
m-Aminobenzenesulphofluoride, B.P. 161 C./ 14
o-Amino-benzene-sulphofluoride, M.P. 62 C.
p-Amino-benzenc-sulphofiuoride, M.P. 68-70 C.,
p-Chlorom-amino-benzene-sulphofluoride, M.P. 69 C.,
p-Dimethyl-amino-m-amino benzene-sulphofluoride, M.P.
p-Methyl-m-amino-benzene-sulphofluoride, M.P. 93 C.
Potassium fluoride may also be allowed to react with acetyl-amino arylene sulphochlorides. The resulting acetylamino-arylene-sulphofiuorides may be de-acylated by means of HCl in alcohol. In this way we have prepared:
p-Methoxy-amino-benzene-sulphofluoride, M.P. 62 C.,
2-Methoxy-5-amino-benzene-sulphofluoride, M.P. 74 C.,
and
2 5 dimethoxy 3 amino benzene sulphofluoride,
M.P. 132 C.
CH (CH COCl (myristoyl-chloride), p-myristoyl-amino-m-nitro-benzenesulphofluoride, M.P. 64 C. (from acetonitrile), is obtained. Reducing the latter with Raney nickel in dioxane at 40-50 C. and under a hydrogen pressure ofi 10-50 atm., eliminating the nickel and evaporating the filtrate until the product crystallizes by cooling, yields p-myristoyl-amino-m-amino-benzene-sulphofluoride, M.P. 122 C.
Condensation of these sulphofluorides with beta-keto esters may be done in the usual way by refluxing the two compounds in toluene or xylene, evaporating the latter after condensation, and recrystallizing the product.
The following compounds were prepared in this way:
rn-(p-Hexadecyl-oxy-benzoyl-acetyl-amino) -benzenesulphofluoride, M.P. 112 C.,
'p-(p-Hexadeeyl-oxy-benzoylracetyl amino) -benzene-sulphofluoride, M.P. 135 C.,
p-Methoxy-m- (p-heXadecyl-oxy-benzoyl acetyl amino)- benzene-sulphofluoride, M.P. 156 C.,
p-Methyl-rn- (p-hexadecyl-oxy-benzoyl-acetylamino) -b enzene-sulphofluoride, M.P. 135 C.,
p-(p-Dodecyl-oXy-benzoyl-acetyl-amino)-benzene-sulphofluoride, M.P. 144 C.,
m- [p-(p-Isooctyl phenoxy ethoxy) benzoyl] acetylamino-benzene-sulphofluoride, M.P. 148 C.,
p-Myristoyl amino-m-benzoyl-acetyl-amino-benzene sulphofiuoride, M.P..160 C.,-
3-(p-hexadecyl-oxy-benzoyl-acetyl amino) 6 methoxybenzene-sulphofluoride, M.P. 105 C.,
3-(p-hexadecyl-oxy-benzoyl acetyl-amino)-4-chloro benzenesulphofluoride, M.P. 132 C.,
3-(p-hexadecyl-oxy-benzoyl-acetyl-amino) -4-methyl benzene-sulphofluoride, M.P. 139 C.,
3 (p-heXadecyl-oxy-benzoylacetylamino) 2-5 -dimethoxybenzene-sulphofluoride, M.P. 120 C.,
m-(p-I-Iexadecyl-oXy-naphthoyl-acetyl amino) benzenesulphofluoride, M.P. 98-99 C.,
m- (4-HeXadecyl-oXy-3-5-dichloro-benzoyl-acetyl-amino) benzene-sulphofluoride, M.P. 132l35 C.,
m-(a-Hexadccyl-oxy-fi-naphthoyl-acetyl-amino)-benzenesulpbofluoride, M.P. 90-92 C.,
m-(p-Hexadecyl-oXy-m-methoXy-benzoyl-acetyl amino)- benzene-sulphofiuoride, M.P. 9799 C., and
p- (Hexadecyl-oxy-m-methoxy-b enzoyl-acetyl-amino) -b en- 'zene-sulphofluorideJMP. 115116 C.
By condensing m-amino-benzene-sulphofluoride with m-nitro benzoyl-acetic acid ethyl ester and reducing the resulting product with Raney nickel in ethyl alcohol at 6080 C. and under a hydrogen pressure of 80-100 atm., m-[m-amino-benzoyl-acetyl-aminol benzene sulphofluoride was obtained. From the latter were obtained, by condensation with palmito-yl chloride and with alpha-hexa-decyl succinic anhydride:
m- (m-palmitoyl-amino-benzoyl-acetyl amino) benzenesulphofluoride, M.P. 96-98 C., and
m[m(Alpha-hexadecyl-succinyl amino)benzoyl acetyllbenzene-sulphofluoride, M.P; 180 C.
In order to convert the sulphofluorides into the correspending sulphonic acids, they are first dissolved in acetone or aqueous dioxane and treated at 60 C. with an aqueous solution of sodium hydroxide. After cooling, the sodium salt of the coupler crystallizes out, or is precipitated by the addition of salt. These sodium salts are recrystallized and may easily be. dissolved in water or in a mixture of water and alcohol for addition to a silver halide emulsion or to a colloid which will form a layer adjacent to a silver halide emulsion layer or separated therefrom by a water-permeable colloid layer.
As primary aromatic amino developing agents may be used mono-, diand tri-amino compounds; as monoamino developers may be mentioned amino phenols and amino cresols, their halogen derivatives, and also amino naphthols.
wherein R represents an aryl radical selected from the group consisting of alkoxyphenyl, alkoXy naphthyl, dialkoxy phenyl, dichloro alkoxy phenyl, isooctyl phenoxy ethoxy phenyl, nitrophenyl, and acylamino phenyl, R" represents a monocyclic arylene radical of the. benzene series, selected from the group consisting of phenylene, chlorophenylene, dialkyl amino phenylene, alkyl phenylene, alkoxy phenylene, dialkoxyphenylene, and acylaminophenylene, and Me represents an alkali metal atom, comprising condensing an 'aroyl acetic ester of the following formula:
wherein R represents a lower alkyl group, with a compound of the formula H N-R'SO F, and hydrolyzing V the resulting compound in the presence of an alkali metal hydroxide.
2. A sulphonated aroyl-acetarylide of the following structure:
wherein R represents an aryl radical selected from the group consisting of alkoxyphenyl, alkoXy naphthyl, dialkoxy phenyl, dichloro alkoxy phenyl, isooctyl phenoxy ethoxy phenyl, nitrophenyl, and acylamino phenyl, R represents a monocyclic arylene radical of the benzene series, selected from the group consisting of phenylene, chlorophenylene, dialkyl amino phenylene, alkyl phenylene, alkoxy phenylene, dialkoxyphenylene, and acylaminophenylene, and Me represents an alkali metal atom, said sulphonated aroyl acetarylide being prepared by condensing an aroyl acetic ester of the following formula: V
RCO'CH -COOR wherein R" represents a lower alkyl group, with a compound of the formula H NR'-SO F, and hydrolyzing the resulting compound in the presence of an alkali metal hydroxide. 7
References Cited in the file of this patent UNITED STATES PATENTS 1,971,409 Henle et a1. Aug. 28, 1934 2,083,962 Petitcolas June 15, 1937 2,303,928 Froehlick et al. Dec. 1, 1942 2,312,040 Kendall et al Feb. 23, 1943 2,748,164. Dodson May 29, 1956

Claims (1)

  1. 2. A SULPHONATED AROYL-ACETARYLIDE OF THE FOLLOWING STRUCTURE:
US575718A 1955-04-05 1956-04-03 Color couplers for color photography Expired - Lifetime US2950314A (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3393040A (en) * 1963-07-09 1968-07-16 Gevaert Photo Prod Nv Silver halide photographic elements containing sulfonic acid substituted aroylacetarylide couplers
US3547987A (en) * 1967-11-13 1970-12-15 Konishiroku Photo Ind Process for the preparation of 3-(4-alkoxybenzoylacetamino) - 4-alkoxybenzenesulfonates

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB976391A (en) * 1960-07-18 1964-11-25 Gevaert Photo Prod Nv Improvements in or relating to gelatin derivatives
BE636699A (en) * 1962-08-31
CH593806A5 (en) * 1974-11-14 1977-12-15 Ciba Geigy Ag

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1971409A (en) * 1930-09-09 1934-08-28 Gen Aniline Works Inc Aroylene-bis-acetic acid-arylides
US2083962A (en) * 1936-03-05 1937-06-15 Cie Nat Matieres Colorantes Process for the manufacture of amino and nitro derivatives
US2303928A (en) * 1940-10-10 1942-12-01 Gen Aniline & Film Corp Process for the production of photographic color images
US2312040A (en) * 1938-07-22 1943-02-23 Ilford Ltd Production of colored photographic images by color development and composition therefor
US2748164A (en) * 1956-05-29 Conhj

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2748164A (en) * 1956-05-29 Conhj
US1971409A (en) * 1930-09-09 1934-08-28 Gen Aniline Works Inc Aroylene-bis-acetic acid-arylides
US2083962A (en) * 1936-03-05 1937-06-15 Cie Nat Matieres Colorantes Process for the manufacture of amino and nitro derivatives
US2312040A (en) * 1938-07-22 1943-02-23 Ilford Ltd Production of colored photographic images by color development and composition therefor
US2303928A (en) * 1940-10-10 1942-12-01 Gen Aniline & Film Corp Process for the production of photographic color images

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3393040A (en) * 1963-07-09 1968-07-16 Gevaert Photo Prod Nv Silver halide photographic elements containing sulfonic acid substituted aroylacetarylide couplers
US3547987A (en) * 1967-11-13 1970-12-15 Konishiroku Photo Ind Process for the preparation of 3-(4-alkoxybenzoylacetamino) - 4-alkoxybenzenesulfonates

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BE546753A (en)
GB808276A (en) 1959-02-04
FR1145045A (en) 1957-10-21

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