US3341331A - Photographic silver halide materials utilizing succinmonoamido benzoyl acetanilide color couplers - Google Patents

Photographic silver halide materials utilizing succinmonoamido benzoyl acetanilide color couplers Download PDF

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US3341331A
US3341331A US354049A US35404964A US3341331A US 3341331 A US3341331 A US 3341331A US 354049 A US354049 A US 354049A US 35404964 A US35404964 A US 35404964A US 3341331 A US3341331 A US 3341331A
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United States
Prior art keywords
coupler
acetanilide
silver halide
succinmonoamido
benzoyl acetanilide
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Expired - Lifetime
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US354049A
Inventor
Kimura Shiro
Tsuda Momotoshi
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Fujifilm Holdings Corp
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Fuji Photo Film Co Ltd
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Priority to US354049A priority Critical patent/US3341331A/en
Priority to GB13538/64A priority patent/GB1045633A/en
Priority to FR969951A priority patent/FR1395930A/en
Priority to DEF43203A priority patent/DE1246405B/en
Priority to BE653518A priority patent/BE653518A/xx
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    • 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

Definitions

  • c.6H33cH cHHcoHNQcocHZcoHN 3 cHzcooH ocH3 cooH 2.
  • 6H33cH cHHCoHNQcocHzcoHNQ cHzcooH ocQHs cooH s.
  • the coupler shows a sutcient solubility in aqueous media and a suitable spectral adsorption for color photography.
  • the presentv invention relates generally to a photograph- .ic sensitivematerial containing a yellow couplerhaving the general formula COOH COCHZCONI-I- t i OR.
  • R is an alkyl group having 8-716 carbon atoms "and R is an alkyl group having 1 4 carbon atoms.
  • Conventional yellow couplers for a subtractive color process are derivatives of lt-keto acid, which have in the molecules at least one carboxyl group or sulfonic acid group as an alkali-soluble group i.e., a group solubilizing the molecule in alkaline media.
  • the alkali-soluble groups of these known derivatives that is, the carboxyl groups or sulfonic acid groups are ones attached to the benzene nucleus of an anilide or the side chain of a benzoyl nucleus, but Vmost o f them are ones attachedto the atomic group of one side of an active methylene group.
  • a coupler which has been usedhitherto has a carboxyl group or carboxyl groups but in the known coupler havatonly one side of the active methylene group, the solubility in an alkali of the coupler cannot be improved remarkably by increasing the number of carboxyl groups. Hence, ⁇ it frequently occurs that the coupler is precipitated when added to an emulsion or even precipitated in an after-treatment step from a photographic sensitive material containing the coupler, which results in reducing markedly the transparency of the image.
  • an object of this invention is to provide a photographic sensitive material containing a yellow coupler having good solubility.
  • Another object of this invention is to provide a color 3,341,331 Patented Sept. 12, 1967 photographic sensitive material having good color reproducing property.
  • a further object of this invention is to provide a color photographic sensitive material which does not have such drawbacks as mentioned above.
  • the coupler employed in this invention contains hydrophilic carboxyl groups in both groups attached to an active methylene group and has very high solubility in an alkali as compared with a conventional coupler containing one or more alkali-soluble groups in only one of the groups attached to the active methylene group. Therefore, the coupler in this invention is not precipitated when it is added in an emulsion or is not precipitated in an after-treatment step, thereby allowing a color image having excellent transparency to be obtained.
  • the absorption spectrum of a pigment shifts always toward the longer wave side of the spectrum when a coupler which contains an electron attractive group such as carboxyl group is used
  • the absorption spectrum of a pigment does not shift toward the longer wave side and the maximum absorption wave length is narrow when the coupler according to this invention is used. Accordingly, the absorption in the green region which adversely affects the color reproduction is very small when the couplers of this invention are employed.
  • the color image obtained from the coupler according to this invention has ⁇ a very excellent durability against the eiect of temperature, humidity and light.
  • Examples of the couplers according to this invention are: l
  • Example 1 200 ml. of an aqueous 5% alkali solution (3.5 ml. of one normal solution -of caustic soda is used per one gramme of coupler) of 5-carboxy-2-methoxy(4-octadecenylsuccinrnonoamido)benzoyl acetanilide (Formula I) is mixed with 1 kg. of a silver halide photographic emulsion and the pH of the solution is adjusted to 7.1-8.0 with caustic soda or citric acid. The mixture is applied on a support such as film, dried, developed with the following developer after exposure, bleached and fixed.
  • a support such as film
  • the yellow image so obtained has its maximum absorption at 440 ma, high transparency and excellent light fastness, and is decolored very little by the effect of temperature and humidity.
  • Example 2 In .place of the coupler of Formula I in Example l, 5 carboxy 2 methoxy (4 tetradecenylsuccinmonoamido)benzoyl acetanilide (Formula II) is used and treated as described in Example l.
  • the yellow image so obtained has its maximum absorption at 440 ma, high transparency and suitable hue.
  • Example 3 In place of the coupler of Formula I in Example 1, 5 carboxy 2 ethoxy (4 octadecenylsuccinmonoamido)benzoyl acetanilide (Formula III) is used and treated as desecribed in Example l.
  • the yellow image so obtained has its maximum absorption at 441 ma, high transparency, land the sharpness 22 ml. of an aqueous 5% alkali solution (3.4 ml. of one normal solution of caustic soda is used per one gramme of coupler) of 3.5-dicarboxy-(4-stearoylmonoamido)benzoyl acetanilide (the comparative coupler) is mixed with g. of the silver halide photographic emulsion used in Example 1, adjusted to the pH value of 7.1- 8.0 with caustic soda or citric acid. The mixture is coated on a support such as lm, dried, then treated as described in Example l.
  • a support such as lm
  • the yellow image so obtained has its maximum absorption at 445 mp., and the absorption in the green region which affects the color reproduction is larger than the absorption obtained from the coupler according to this invention.
  • absorption curves 1, 2 and 3 of dyes obtained by development of a silver halide emulsion with a N,Ndiethylparaphenylene diamine in the presence of the compounds of Formulas I, and III and the comparative coupler having the structure shown in the legend of the drawing.
  • the spectroscopic absorption curves obtained by the normalized maximum absorption of visible region are used.
  • the maximum absorption obtained with couplers of Formulas I, II, III, and the comparative coupler of Example 4 are also shown in the following table.

Description

Sept.
12, 1967 sHlRo KIMURA ETAL PHOTOGRAPHIC SILVER HALIDE MATERIALS UTILIZING SUCCINMONOAMIDO BENZOYL ACETANILIDE COLOR COUPLERS Filed Maren 2s, 1964 DYES MADE FROM: 4
Y cooH l. c.6H33cH=cHHcoHNQcocHZcoHN 3 cHzcooH ocH3 cooH 2. c|6H33cH=cHHCoHNQcocHzcoHNQ cHzcooH ocQHs cooH s. cH35c0HNOc0cH2coHNC cooH WAVELENGTH IN MILLIMICRONS INVENTORS im u r a Shir-O ing the carboxyl group or groups A caboxyl or sulfonic United States Patent Oiiice ABSTRACT OF THE DISCLOSURE A yellow-forming component or color coupler for silver halide emulsions used in light-sensitive color photography having the following general formula CO CHnC ON H- RCH=CHCH CON E@ OR OHiCOOH COOH wherein R is an alkyl group having 8-16 carbon atoms and R is an alkyl group having l-4 carbon atoms. The coupler shows a sutcient solubility in aqueous media and a suitable spectral adsorption for color photography.
` The presentv invention relates generally to a photograph- .ic sensitivematerial containing a yellow couplerhaving the general formula COOH COCHZCONI-I- t i OR.
CHzCOOH wherein R is an alkyl group having 8-716 carbon atoms "and R is an alkyl group having 1 4 carbon atoms.
. Conventional yellow couplers for a subtractive color process are derivatives of lt-keto acid, which have in the molecules at least one carboxyl group or sulfonic acid group as an alkali-soluble group i.e., a group solubilizing the molecule in alkaline media. The alkali-soluble groups of these known derivatives, that is, the carboxyl groups or sulfonic acid groups are ones attached to the benzene nucleus of an anilide or the side chain of a benzoyl nucleus, but Vmost o f them are ones attachedto the atomic group of one side of an active methylene group.
A coupler which has been usedhitherto has a carboxyl group or carboxyl groups but in the known coupler havatonly one side of the active methylene group, the solubility in an alkali of the coupler cannot be improved remarkably by increasing the number of carboxyl groups. Hence,` it frequently occurs that the coupler is precipitated when added to an emulsion or even precipitated in an after-treatment step from a photographic sensitive material containing the coupler, which results in reducing markedly the transparency of the image.
Further, when a coupler is used in which at least one acid group is introduced into the benzene nucleus of -keto acid anilde, not only is the absorption spectrum of thus formed pigment shifted to the longer wave length side of the spectrum but valso the absorption in green regions of the spectrum is broadened, which adversely aects the color reproduction.
Therefore, an object of this invention is to provide a photographic sensitive material containing a yellow coupler having good solubility.
Another object of this invention is to provide a color 3,341,331 Patented Sept. 12, 1967 photographic sensitive material having good color reproducing property.
A further object of this invention is to provide a color photographic sensitive material which does not have such drawbacks as mentioned above.
The coupler employed in this invention contains hydrophilic carboxyl groups in both groups attached to an active methylene group and has very high solubility in an alkali as compared with a conventional coupler containing one or more alkali-soluble groups in only one of the groups attached to the active methylene group. Therefore, the coupler in this invention is not precipitated when it is added in an emulsion or is not precipitated in an after-treatment step, thereby allowing a color image having excellent transparency to be obtained.
While the absorption spectrum of a pigment shifts always toward the longer wave side of the spectrum when a coupler which contains an electron attractive group such as carboxyl group is used, the absorption spectrum of a pigment does not shift toward the longer wave side and the maximum absorption wave length is narrow when the coupler according to this invention is used. Accordingly, the absorption in the green region which adversely affects the color reproduction is very small when the couplers of this invention are employed.
Moreover, the color image obtained from the coupler according to this invention has `a very excellent durability against the eiect of temperature, humidity and light.
As described above, a natural color image of excellent color reproduction can be obtained when the couplers according to this invention-is used.
Examples of the couplers according to this invention are: l
/COOH -COCHZCOHNQ o ou,
(Il) S-carboxy-Z-methoxy-(4-tetradecenylsuccinmonoamido) benzoyl acetanilide,
COOH
l -oocmooHN-O (III) 5-carboxy-2-ethoxy-(4-octadecenylsuccinmonoamido)benzoyl acetanilide,
oooH
-oooHlooHN-O CH2() 0 OH I COCHaC OHN CHzCOOH 1. SYNTHESIS OF CARBOXY 2 METHOXY- (4 OCTADECENYLSUCCINMONOAMIDO)BEN- ZOYL ACETANILIDE One mole of 5-carboxy-2-methoxy-(4-aminobenzoyl) acetanilide and 1 mole of octadecenyl succinic anhydride .are put in a three neck ask, one liter of dimethyl formaldehyde is added, and they are heated to 95 C. with stirring and reacted at that temperature for 4 hrs. After reaction, the product is cooled to normal temperature, poured in 7 liters of ice water to deposit crystals. It is filtered under suction, washed well with water, and dried. On recrystallizing from methanol, the above-identified acetanilide which decomposes at G-159 C. is obtained.
Yield: 60%.
2. SYNTHESIS OF 5 CARBOXY 2 METHOXY- (4-TETRADECENYLSUCCINMONOAMIDO BEN- ZOYL ACETANILIDE To 1 mole of 5-carboxy-2-methoxy-(4-aminobenzoyl) acetanilide and l mole of tetradecenyl succinic anhydride is added 1 liter of dimethyl formaldehyde and they are treated as described in l. The above-identified acetanilide which melts at 15S-156 C. is obtained.
Yield: 60%.
3. SYNTHESIS OF 5 CARBOXY 2 ETHOXY- (4 OCTADECENYLSUCCINMONOAMIDO)BEN- ZOYL ACETANILIDE To 1 mole of 5-carboxy-2-ethoxy- (4-aminobenzoyl) acetanilide and 1 mole of octadecenyl succinic anhydride is added 1 liter of dimethyl formaldehyde and they are treated as described in l. The above-identified acetanilide which melts at 163-165 C. is obtained.
Yield: 65%.
The use of the couplers is further illustrated by the following examples.
Example 1 200 ml. of an aqueous 5% alkali solution (3.5 ml. of one normal solution -of caustic soda is used per one gramme of coupler) of 5-carboxy-2-methoxy(4-octadecenylsuccinrnonoamido)benzoyl acetanilide (Formula I) is mixed with 1 kg. of a silver halide photographic emulsion and the pH of the solution is adjusted to 7.1-8.0 with caustic soda or citric acid. The mixture is applied on a support such as film, dried, developed with the following developer after exposure, bleached and fixed.
l G. N,Ndiethyl par-aphenylene diamine 2.0 Sodium sulte 2.0 Sodium carbonate 20.0 Potassium bromide Balance water to make l liter.
The yellow image so obtained has its maximum absorption at 440 ma, high transparency and excellent light fastness, and is decolored very little by the effect of temperature and humidity.
Example 2 In .place of the coupler of Formula I in Example l, 5 carboxy 2 methoxy (4 tetradecenylsuccinmonoamido)benzoyl acetanilide (Formula II) is used and treated as described in Example l.
The yellow image so obtained has its maximum absorption at 440 ma, high transparency and suitable hue.
Example 3 In place of the coupler of Formula I in Example 1, 5 carboxy 2 ethoxy (4 octadecenylsuccinmonoamido)benzoyl acetanilide (Formula III) is used and treated as desecribed in Example l.
The yellow image so obtained has its maximum absorption at 441 ma, high transparency, land the sharpness 22 ml. of an aqueous 5% alkali solution (3.4 ml. of one normal solution of caustic soda is used per one gramme of coupler) of 3.5-dicarboxy-(4-stearoylmonoamido)benzoyl acetanilide (the comparative coupler) is mixed with g. of the silver halide photographic emulsion used in Example 1, adjusted to the pH value of 7.1- 8.0 with caustic soda or citric acid. The mixture is coated on a support such as lm, dried, then treated as described in Example l.
The yellow image so obtained has its maximum absorption at 445 mp., and the absorption in the green region which affects the color reproduction is larger than the absorption obtained from the coupler according to this invention.
In the drawing are shown absorption curves 1, 2 and 3 of dyes obtained by development of a silver halide emulsion with a N,Ndiethylparaphenylene diamine in the presence of the compounds of Formulas I, and III and the comparative coupler having the structure shown in the legend of the drawing. The spectroscopic absorption curves obtained by the normalized maximum absorption of visible region are used. The maximum absorption obtained with couplers of Formulas I, II, III, and the comparative coupler of Example 4 are also shown in the following table.
Formula: Maximum absorption, mp. I 440 II 440 III 441 Comparative coupler 445 In the next table are shown the degradative ratio of blue filter density resulting from the exposure of the yellow image containing the indicated couplers for 7 days at 50 C., 90% relative humidity.
In the next table are shown the degradative ratio of blue filter density resulting from the exposure of the yellow image containing the indicated couplers for l2 hours by Xenon-tester (Shimazu XF-20 type).
Formula: Degradative ratio, percent I 43' II 42 III v 40 Comparative coupler 53 wherein R is an alkyl group having 8-16 carbon atoms and R' is an alkyl group having 1-4 carbon atoms.
2. The photographic sensitive material as claimed in claim 1 wherein said coupler is 5carboxy2methoxy(4 octadecenylsuccinmonoamido)benzoyl acetanilide.
3. The photographic sensitive material as claimed in claim 1 wherein said coupler is 5carboXy2methoXy-(4 tetradecenylsuccinmonoamido) benzoyl acetanilide.
4. The photographic sensitive material as claimed in claim 1 wherein said coupler is 5-carboxy-2-ethoxy-(4-ootadecenylsuccinmonoamido)benzoyl acetanilide.
5. The photographic sensitive material as claimed in claim 1 wherein said coupler is S-carboxy-Z-methoxy-(3- octadecenylsuccinmonoamido)benzoyl acetanilide.
6. The photographic sensitive material as claimed in claim 1 wherein said coupler is S-carboxy-Z-methoXy-(4- dodecenylsuccinmonoamido) benzoyl acetanilide.
7. A light sensitive silver halide photographic emulsion containing a non-diffusing coupler compound of the general formula OR CHICOOH COOH OR' CHzC 0 OH wherein R is an alkyl group having 8-16 carbon atoms and R is an alkyl group having 1-4 carbon atoms.
References Cited UNITED STATES PATENTS 3,056,674 10/ 1962 Hofstadt et al.
I. TRAVIS BROWN, Primary Examiner. NORMAN G. TORCHIN, Examiner.

Claims (1)

  1. 8. THE PROCESS OF PRODUCING A YELLOW DYESTUFF IMAGE IN A SILVER HALIDE EMULSION WHICH COMPRISES EXPOSING SAID EMULSION TO LIGHT AND DEVELOPING THE SAME WITH A PRIMARY AROMATIC AMINO DEVELOPER IN THE PRESENCE OF A
US354049A 1964-03-23 1964-03-23 Photographic silver halide materials utilizing succinmonoamido benzoyl acetanilide color couplers Expired - Lifetime US3341331A (en)

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US354049A US3341331A (en) 1964-03-23 1964-03-23 Photographic silver halide materials utilizing succinmonoamido benzoyl acetanilide color couplers
GB13538/64A GB1045633A (en) 1964-03-23 1964-04-01 Novel benzoylacetanilide derivatives and their use in colour photographic materials
FR969951A FR1395930A (en) 1964-03-23 1964-04-07 Photographic sensitive materials
DEF43203A DE1246405B (en) 1964-03-23 1964-06-18 Color photographic material with a color coupler for yellow
BE653518A BE653518A (en) 1964-03-23 1964-09-24

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BE653518A BE653518A (en) 1964-03-23 1964-09-24

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5443858A (en) * 1993-11-18 1995-08-22 Golden Valley Microwave Foods, Inc. Composition for sweetening microwave popcorn; method and product
US5585127A (en) * 1995-03-02 1996-12-17 Golden Valley Microwave Foods, Inc. Composition and method for flavoring popped popcorn
US5750166A (en) * 1996-08-29 1998-05-12 Golden Valley Microwave Foods, Inc. Composition and method for flavoring popcorn product
JP2011524340A (en) * 2008-05-21 2011-09-01 ニュー・ワールド・ラボラトリーズ・インコーポレイテッド Selective caspase inhibitors and uses thereof
US8883235B2 (en) 2011-02-23 2014-11-11 Conagra Foods Rdm, Inc. Ingredient delivery system for popcorn kernels
US9045524B2 (en) 2009-05-21 2015-06-02 Novagenesis Foundation Selective caspase inhibitors and uses thereof
US9944674B2 (en) 2011-04-15 2018-04-17 Genesis Technologies Limited Selective cysteine protease inhibitors and uses thereof

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3056674A (en) * 1961-02-01 1962-10-02 Gen Aniline & Film Corp Color formers for producing yellow dye images by color development

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3056674A (en) * 1961-02-01 1962-10-02 Gen Aniline & Film Corp Color formers for producing yellow dye images by color development

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5443858A (en) * 1993-11-18 1995-08-22 Golden Valley Microwave Foods, Inc. Composition for sweetening microwave popcorn; method and product
US5585127A (en) * 1995-03-02 1996-12-17 Golden Valley Microwave Foods, Inc. Composition and method for flavoring popped popcorn
US5688543A (en) * 1995-03-02 1997-11-18 Golden Valley Microwave Foods, Inc. Composition and method for flavoring unpopped popcorn
US5750166A (en) * 1996-08-29 1998-05-12 Golden Valley Microwave Foods, Inc. Composition and method for flavoring popcorn product
EP2288615B1 (en) * 2008-05-21 2017-06-21 Genesis Technologies Limited Selective caspase inhibitors and uses thereof
JP2015110593A (en) * 2008-05-21 2015-06-18 ニュー・ワールド・ラボラトリーズ・インコーポレイテッドＮｅｗ Ｗｏｒｌｄ Ｌａｂｏｒａｔｏｒｉｅｓ Ｉｎｃ． Selective caspase inhibitors and uses thereof
US9562069B2 (en) 2008-05-21 2017-02-07 Genesis Technologies Limited Selective caspase inhibitors and uses thereof
JP2011524340A (en) * 2008-05-21 2011-09-01 ニュー・ワールド・ラボラトリーズ・インコーポレイテッド Selective caspase inhibitors and uses thereof
US10167313B2 (en) 2008-05-21 2019-01-01 Genesis Technologies Limited Selective caspase inhibitors and uses thereof
US9045524B2 (en) 2009-05-21 2015-06-02 Novagenesis Foundation Selective caspase inhibitors and uses thereof
US8883235B2 (en) 2011-02-23 2014-11-11 Conagra Foods Rdm, Inc. Ingredient delivery system for popcorn kernels
US9944674B2 (en) 2011-04-15 2018-04-17 Genesis Technologies Limited Selective cysteine protease inhibitors and uses thereof
US10975119B2 (en) 2011-04-15 2021-04-13 Genesis Technologies Limited Selective cysteine protease inhibitors and uses thereof

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BE653518A (en) 1965-01-18

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