US3816134A - Photographic color developing solutions containing p-toluenesulfonic acid salts of p-phenylenediamines - Google Patents

Photographic color developing solutions containing p-toluenesulfonic acid salts of p-phenylenediamines Download PDF

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Publication number
US3816134A
US3816134A US00204725A US20472571A US3816134A US 3816134 A US3816134 A US 3816134A US 00204725 A US00204725 A US 00204725A US 20472571 A US20472571 A US 20472571A US 3816134 A US3816134 A US 3816134A
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United States
Prior art keywords
ethyl
phenylenediamine
toluenesulfonic acid
color developing
salt
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Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
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US00204725A
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English (en)
Inventor
D Schellenberg
R Bent
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Eastman Kodak Co
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Eastman Kodak Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority to BE792265D priority Critical patent/BE792265R/xx
Application filed by Eastman Kodak Co filed Critical Eastman Kodak Co
Priority to US00204725A priority patent/US3816134A/en
Priority to CA141,663A priority patent/CA994807A/en
Priority to DE19722248906 priority patent/DE2248906A1/de
Priority to FR7242722A priority patent/FR2164220A6/fr
Priority to IT7232471A priority patent/IT971529B/it
Priority to GB5589172A priority patent/GB1416699A/en
Priority to JP47120778A priority patent/JPS5220140B2/ja
Priority to US435813A priority patent/US3907875A/en
Application granted granted Critical
Publication of US3816134A publication Critical patent/US3816134A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • G03C7/407—Development processes or agents therefor
    • G03C7/413—Developers
    • G03C7/4136—Developers p-Phenylenediamine or derivatives thereof

Definitions

  • p-phenylenediamine salts are the di-p-toluenesulfonic acid salts of 3-alkyl and 3-alkoxy N- alkyl-N-alkoxyalkyl-p-phenylenediamine developing agents.
  • Color development of the differently sensitized emulsion layers in color photographic elements containing nondiffusible couplers is advantageously performed in a single color development step to produce a color negative image reproduction when this development step is the first development step, or to produce a color reversal image if a negative black-and-white development step is used followed by a step in which the residual unexposed and undeveloped silver halide is made developable and then color developed.
  • diffusible couplers are used in the aqueous alkaline color developer solutions that are used to selectively color develop one silver halide emulsion layer at a time.
  • the silver and any residual silver halide are removed by silver bleaching and then fixing the photographic element.
  • R, and R are alkyl groups having from 1 to 4 carbon atoms i.e. methyl,-ethyl, propyl, butyl etc., hydroxy alkyl groups having from 1 to 4 carbon atoms i.e. hydroxy methyl, hydroxy ethyl, etc., or alkoxy alkyl groups having from 2 to 8 carbon atoms i.e. methoxy methyl, methoxy ethyl, ethoxy methyl, ethoxy ethyl etc. and R is an alkyl or alkoxy group having from 1 to 4 carbon atoms have been found to have unusually and unexpectedly high solubility in aqueous alkaline solutron.
  • R is an alkyl group having 1 to 4 carbon atoms, e.g. methyl, ethyl, propyl,
  • butyl, etc. and R is an alkyl group having from 1 to 4 carbon atoms, e.g. methyl, ethyl, propyl, butyl etc., or an alkoxy group having from 1 to 4 carbon atoms, e.g. methoxy, ethoxy, propoxy, butoxy.
  • Typical representative examples" of the preferred color developing agents of Formula I are the following:
  • .are prepared by reacting the appropriate w-alkoxyalkyl chloride or bromide with the appropriate N-ethyl- '3-alkyl-aniline or N-ethyl-3-alkoxyaniline.
  • the tertiary anilines formed by this reaction are then either nitrosated or azo-coupled followed by catalytic hydrogenation to give the corresponding p-phenylenediamine.
  • the p-toluenesulfonic acid salts of these materials are generally prepared by forming the 4-(2,5- Dichlorophenylazo) derivative of the pphenylenediamine derivative of Formula 1, reducing the azo dye and adding p-toluenesulfonic acid.
  • the di-p-toluenesulfonic acid salt of Preferred Color Developing Agent 3 is advantageously prepared by the following sequence of reactions:
  • N-(B-Ethoxyethyl )-N-ethyl-3-methylaniline Amixture of 135 g (1 mole) of N-ethyl-3-aniline, 153 g (1 mole) of 2-bromoethyl ethyl ether (purified by treatment with sodium bicarbonate and distillation), 88.2 g (1.05 mole) of sodium bicarbonate, 1,100 ml of ethanol and 290 ml of water are refluxed for a total'of 64 hours.
  • the ethanol is removed by distillation and the oil layer is extracted with ether; the ether extracts are dried and concentrated, followed by distillation of the residual oil under reduced pressure. After removal of the lower boiling foreruns, the fraction, b .p. 9295C/ 1mm (overheats readily) is collected. The yield of I is approximately percent.
  • the mixture is cooled to about 25C and allowed to stand undisturbed overnight.
  • the developer salt is filtered off and washed in a funnel with small portions of isopropyl alcohol.
  • the yield of Developing Agent 3, mp. 214 216C, is approximately 70 percent.
  • the di-p-toluenes'ulfonic acid salt of Color Developing Agent 5 is advantageously prepared similarly to developing agent (3), using N-ethyl-3-methoxyaniline and 2-bromoethyl methyl ether as starting materials.
  • N-Ethyl-3-methoxy-N-(B-methoxyethyD-aniline A mixture of 100 g (0.661 mole) of N-ethyl-3- methoxyaniline, 92 g (0.661 mole) of 2-bromoethyl methyl ether, 55.8 g (0.6665 mole) of sodium bicarbonate, 1,000 ml of ethanol and 280 m1 of water is refluxed for a total of 68 hours.
  • the di-p-toluenesulfonic acid salt of 4-amino-N- ethyl-3-methoxy-N-(B-methoxyethyl )aniline (Developing Agent 5) Exactly 4.86 g (0.127 mole) of the azo dye, IV, is reduced on Parr shaker, using 300 ml of absolute alcohol and Raney nickel as catalyst. When complete, the catalyst is filtered off, washed on funnel with more alcohol. Av total of 4.84 g (0.0254 mole) of p-toluenesulfonic acid (hydrate) in 50 m1 of ethanol is added; no precipitate occurs and the solution is concentrated to dryness under partial vacuum.
  • the gummy residue is then dissolved in a small quantity of absolute alcohol and a large excess of ethyl ether is added; the developer salt again comes out as a gum; the solution is cooled thoroughly (refrigerator) to precipitate the suspension and then the ether-alcohol layer is decanted. This treatment is repeated twice more to remove all of the regenerated 2,5-dichloroaniline. Finally, the developer salt is slurried thoroughly with ether only, gradually becoming crystalline; it is dried in a vacuum oven. The yield of Developing Agent 5, mp. 160 162C, is 62 percent.
  • the di-p-toluenesulfonic acid salt of Color Developing Agent 1 is made in a manner similar to the synthesis described for the corresponding acid salt of Color Developing Agent 5, excepting that an equimolar amount of N-ethyl-3-methylaniline is used in place of N-ethyl- 3-methoxyaniline.
  • the di-p-toluenesulfonic acid salt of Color Developing Agent 2 is made in a manner similar to the synthesis described for the corresponding acid salt of Color Developing Agent 5, excepting that an equimolar amount of arbromobutyl methyl ether is used in place of 2- bromoethyl methyl ether.
  • the di-p-toluenesulfonic acid salt of Color Develop ing Agent 4 is advantageously made in a manner similar to that described for the corresponding acid salt of Color Developing Agent 3, excepting that an equimolar amount of N-ethyl-3-propylaniline is used in place of N-ethyl-3-methylaniline.
  • Still other color developing agents of Formula I are made using the synthesis illustrated herein using the appropriate starting materials and intermediates.
  • EXAMPLE 1 The procedure described in Example 1 was repeated with solutions of dilferent pH values. The results are tabulated in Table 2.
  • EXAMPLE 3 The procedure described in Example 1 was repeated by adding the developer salt to sodium carbonate solutions of 25, or 320 g/l, respectively, to simulate actual color developer solutions. The results are tabulated in Table 3.
  • EXAMPLE 4 The procedure described in Example 1 was repeated by adding the developer salt to solutions with 50, 100 or 150 g/l NaPTS. The results are summarized in Table 4.
  • EXAMPLE 5 The procedure described in Example 1 was repeated by adding the developer salt to a solution with g/l NaPT S. The results are given in Table 5.
  • Example 6 will serve to further distinguish the method and compositions of the present in- TABLE 5 vention from those of the prior art.
  • these organic acid salts of pphenylenediamine developing agents will be used in aqueous alkaline solution at a pH above about 8 and preferably above about 9.5.
  • concentration of the salt present in the solution will be dependent upon the concentration of developing agent which is required. Generally, this concentration will range from about 0.5 to about g/] in working developer compositions depending upon the particular system to which the developer is to be applied.
  • concentration of PT S salt is limited only by its own solubility and the stability of such a solution under a given set of conditions of storage and shipping.
  • the concentration of the PTS salt is limited by the use to which the solution is to be put and hence the amount of developer which it is sought to have present therein.
  • the specific color developing agents described in Formula ll hereinabove are concerned, the problem of color developer solubility no longer exists since the limits of the solubility of the FT S salts of these materials are generally at or well above the practical concentration limits for those materials in working solutions.
  • PT S p-phenylenediamines with p-toluenesulfonic acid
  • droxy lower alkyl, or alkoxy lower alkyl and R is lower alkyl or lower alkoxy have unexpectedly high solubility in aqueous alkaline solutions of the type utilized for the color development of color photographic elements and that hence they possess all of the above-described advantages incident to such unusually high solubility.
  • Solutions of these materials can of course include all of the addenda incident to developer compositions of the type described including but not limited to color developer stabilizing agents, alkali metal chloride, alkali metal bromide, sulfite ion and the alkali metal salts of weak acids.
  • Solutions of the PT S salts of the color developers described by Formulas I and II are formed simply by dissolving the same in an aqueous alkaline solution.
  • the working developer solutions can comprise up to about 200 g/l of color developing agent although much lower concentration levels on the order of from about 0.5 to about 15 g/l will provide satisfactory results in conventional processes as mentioned above. Concentrations above this level are useful when it is sought to speed up the development rate and/or to increase the throughput capability of the developer bath.
  • concentrated aqueous alkaline solutions of the PT S salts of the developing agent i.e. those solutions having concentrations above about 200 g/l will generally be prepared for shipping and storage.
  • concentrates may contain as much of the salt as tolerable in the particular system so that precipitation or phase separation does not occur.
  • these concentrates When received by the consumer-processor these concentrates will be diluted with water to provide working solutions with color developer agent concentration of up to, for example, perhaps 200 g/l.
  • the concentrate will generally contain a sufficient amount of alkali i.e. sodium, potassium or ammonium hydroxide or sodium 0r potassium carbonate to provide when dissolved in water to yield the desired developing agent concentration, a solution of the developing agent which has a pH above about 8 and preferably above about 9.5.
  • the active developing agent of working developer solutions prepared from such concentrates are pphenylenediamine developing agents they will include small amounts of sulfite ion which stabilize the developing agent against aerial oxidation during storage as a concentrate and while in use as a working developer solution.
  • benzyl alcohol (0-15 ml/l) alkali metal chlorides (0-15 g/l), alkali metal bromides (0.1-1.0 g/l), alkali metal or ammonium sulfite (0.1-5.0 g/l) and alkali metal or ammonium salts of weak acids (10.0-50.0 g/l) which are conventionally present in pphenylenediamine developer solutions of this type in the concentration ranges shown in parentheses
  • a stabilizer composition which insures that the developer does not separate into phases at levels of from about 0.1 to about 5.0 g/l.
  • Two such stabilizers are hydroxylamine sulfate and dihydroxyacetone. 7
  • the color development of a multilayer silver halide color emulsion layer is accomplished by contacting the silver halide with an aqueous alkaline solution of a p-phenylenediamine developing agent in the presence of a coupler that reacts with oxidized developing agent to form a dye.
  • the improvement in such a process comprises using the p-toluenesulfonic acid salt of the pphenylenediamine developing agent as the developing agent to provide higher concentrations of developing agent than would normally otherwise be possible.
  • lQAn aqueous alkaline photographic color developing solution containing, as the color developing agent, a p-toluenesulfonic acid salt which is highly soluble in aqueous alkaline solutions, said p-toluenesulfonic acid salt having the formula:
  • m is an integer having a value of from 2 to 4,
  • R is an alkyl group of l to 4 carbon atoms and R is a member selected from the group consisting of alkyl groups of l to 4 carbon atoms and alkoxy groups of l to 4 carbon atoms.
  • n is an integer having a value of from 2 to 4,
  • R is an alkyl group of l to 4 carbon atoms and R is a member selected from the group consisting of alkyl 13 14 groups of 1 to 4 carbon atoms and alkoxy groups of 1 4.
  • V N-Ethyl-N-methoxyethyL3-n-propyl-pto 4 carbon atoms. phenylenediamine;
  • said salt is a 5, N-ethyl-N-methoxyethyl-3-methoxy-pdi-p-toluenesulfonic acid salt of a member selected phenylenediamine; from the group consisting of: 5 and l N-Ethyl-N-methoxyethyl-3-methyl-p- 6. N-Ethyl-N-butoxyethyl-3-methyl-pphenylenediamine; phenylenediamine. 2. N-Ethyl-N-methoxybutyl-3-methyl-p- 9.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US00204725A 1971-12-03 1971-12-03 Photographic color developing solutions containing p-toluenesulfonic acid salts of p-phenylenediamines Expired - Lifetime US3816134A (en)

Priority Applications (9)

Application Number Priority Date Filing Date Title
BE792265D BE792265R (fr) 1971-12-03 Procede de traitement photographique en couleurs et composes chimiques utiles pour la mise en oeuvre de ce
US00204725A US3816134A (en) 1971-12-03 1971-12-03 Photographic color developing solutions containing p-toluenesulfonic acid salts of p-phenylenediamines
CA141,663A CA994807A (en) 1971-12-03 1972-05-09 Color developers
DE19722248906 DE2248906A1 (de) 1971-12-03 1972-10-05 Farbphotographisches entwicklungsverfahren und farbentwickler zur durchfuehrung des verfahrens
FR7242722A FR2164220A6 (en, 2012) 1971-12-03 1972-12-01
IT7232471A IT971529B (it) 1971-12-03 1972-12-04 Materiali per fotografia
GB5589172A GB1416699A (en) 1971-12-03 1972-12-04 Salts of substituted p-phenylene diamine developing agents and their use in colour photography
JP47120778A JPS5220140B2 (en, 2012) 1971-12-03 1972-12-04
US435813A US3907875A (en) 1971-12-03 1974-01-23 Di-p-toluenesulfonic acid salt of N-ethyl-N-methoxyethyl-3-methyl 1,4 benzenediamine

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US00204725A US3816134A (en) 1971-12-03 1971-12-03 Photographic color developing solutions containing p-toluenesulfonic acid salts of p-phenylenediamines

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US (1) US3816134A (en, 2012)
JP (1) JPS5220140B2 (en, 2012)
BE (1) BE792265R (en, 2012)
CA (1) CA994807A (en, 2012)
DE (1) DE2248906A1 (en, 2012)
FR (1) FR2164220A6 (en, 2012)
GB (1) GB1416699A (en, 2012)
IT (1) IT971529B (en, 2012)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2613120A1 (de) * 1976-03-27 1977-10-06 Agfa Gevaert Ag Verfahren zur entwicklung von farbphotographischen bildern mit p-dialkylaminoanilin-farbentwicklern
US4113491A (en) * 1975-02-10 1978-09-12 Konishiroku Photo Industry Co., Ltd. Color photographic developing composition
US4394440A (en) * 1982-01-22 1983-07-19 Eastman Kodak Company Yellow-dye-forming photographic developing composition
US4481268A (en) * 1981-02-09 1984-11-06 Eastman Kodak Company Method of forming a photographic dye image
EP1156365A1 (en) * 2000-05-17 2001-11-21 Agfa-Gevaert A concentrate comprising a p-phenylenediamine derivative

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2281594A1 (fr) * 1974-08-06 1976-03-05 Hunt Chem Corp Philip A Revelateur chromogene concentre et son procede de preparation
JPS5180229A (ja) * 1975-01-07 1976-07-13 Konishiroku Photo Ind Karaagenzoyososeibutsu
JPS5823618B2 (ja) * 1975-12-22 1983-05-16 コニカ株式会社 カラ−シヤシンヨウゲンゾウザイ
JPS59188641A (ja) 1983-04-11 1984-10-26 Fuji Photo Film Co Ltd ハロゲン化銀写真乳剤
JPS61245151A (ja) 1985-04-23 1986-10-31 Konishiroku Photo Ind Co Ltd ハロゲン化銀写真感光材料
JPS61250643A (ja) 1985-04-30 1986-11-07 Konishiroku Photo Ind Co Ltd ハロゲン化銀写真感光材料
JPS61250645A (ja) 1985-04-30 1986-11-07 Konishiroku Photo Ind Co Ltd ハロゲン化銀写真感光材料
JPS61255342A (ja) 1985-05-09 1986-11-13 Fuji Photo Film Co Ltd ハロゲン化銀カラ−写真感光材料
DE3682128D1 (de) 1985-07-17 1991-11-28 Konishiroku Photo Ind Photographisches silberhalogenidmaterial.
JPH0711695B2 (ja) 1985-09-25 1995-02-08 富士写真フイルム株式会社 撮影用ハロゲン化銀カラー感光材料の処理方法
US4892803A (en) 1986-01-23 1990-01-09 Fuji Photo Film Co., Ltd. Color image-forming process compressing developer containing no benzyl alcohol
EP0239363B1 (en) 1986-03-25 1992-10-28 Konica Corporation Light-sensitive silver halide photographic material feasible for high speed processing
EP0456210B1 (en) 1990-05-09 1999-10-13 Fuji Photo Film Co., Ltd. Method for processing a silver halide photographic material and light-sensitive material for photographing
JP2824717B2 (ja) 1992-07-10 1998-11-18 富士写真フイルム株式会社 ハロゲン化銀写真感光材料の処理方法
EP0589460B1 (en) 1992-09-24 2000-08-09 Fuji Photo Film Co., Ltd. Method for processing a black & white silver halide light-sensitive material
DE69516054T2 (de) 1994-07-18 2000-10-26 Konica Corp., Tokio/Tokyo Photographisches Silberhalogenidelement und sein Verarbeitungsverfahren
DE69515939T2 (de) 1994-08-11 2000-07-20 Konica Corp., Tokio/Tokyo Verfahren zur Verarbeitung eines photographischen lichtempfindlichen Silberhalogenidmaterials
JP3574986B2 (ja) 1996-01-16 2004-10-06 コニカミノルタホールディングス株式会社 ハロゲン化銀写真感光材料用固体処理剤及びハロゲン化銀写真感光材料の処理方法
US5773203A (en) * 1996-05-16 1998-06-30 Fuji Photo Film Co., Ltd. 4-(N,N-dialkylamino)aniline compounds, photographic processing composition containing the same and color image-forming method
US5994546A (en) * 1997-05-14 1999-11-30 Fuji Photo Film Co., Ltd. 4-(N,N-dialklylamino)aniline compounds, photographic processing composition containing the same and color image-forming method

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3656950A (en) * 1970-12-03 1972-04-18 Eastman Kodak Co Color photographic processes
US3658525A (en) * 1970-12-03 1972-04-25 Eastman Kodak Co Reversal color photographic processes

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3656950A (en) * 1970-12-03 1972-04-18 Eastman Kodak Co Color photographic processes
US3658525A (en) * 1970-12-03 1972-04-25 Eastman Kodak Co Reversal color photographic processes

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4113491A (en) * 1975-02-10 1978-09-12 Konishiroku Photo Industry Co., Ltd. Color photographic developing composition
DE2613120A1 (de) * 1976-03-27 1977-10-06 Agfa Gevaert Ag Verfahren zur entwicklung von farbphotographischen bildern mit p-dialkylaminoanilin-farbentwicklern
US4481268A (en) * 1981-02-09 1984-11-06 Eastman Kodak Company Method of forming a photographic dye image
US4394440A (en) * 1982-01-22 1983-07-19 Eastman Kodak Company Yellow-dye-forming photographic developing composition
EP1156365A1 (en) * 2000-05-17 2001-11-21 Agfa-Gevaert A concentrate comprising a p-phenylenediamine derivative
US6468723B2 (en) 2000-05-17 2002-10-22 Agfa-Gevaert N.V. Concentrate comprising a p-phenylenediamine derivative

Also Published As

Publication number Publication date
JPS5220140B2 (en, 2012) 1977-06-01
DE2248906A1 (de) 1973-06-07
JPS4864933A (en, 2012) 1973-09-07
BE792265R (fr) 1973-06-04
IT971529B (it) 1974-05-10
FR2164220A6 (en, 2012) 1973-07-27
GB1416699A (en) 1975-12-03
CA994807A (en) 1976-08-10

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