US3128182A - Silver halide solvent containing developers and process - Google Patents

Silver halide solvent containing developers and process Download PDF

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Publication number
US3128182A
US3128182A US147055A US14705561A US3128182A US 3128182 A US3128182 A US 3128182A US 147055 A US147055 A US 147055A US 14705561 A US14705561 A US 14705561A US 3128182 A US3128182 A US 3128182A
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photographic
silver halide
color
pyrazolone
cyclohexane
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US147055A
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Charleton C Bard
Allan G Millikan
Jr Deane S Thomas
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Eastman Kodak Co
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Eastman Kodak Co
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Priority to US147055A priority patent/US3128182A/en
Priority to DEP1269A priority patent/DE1269484B/en
Priority to FR912638A priority patent/FR1336560A/en
Priority to GB40182/62A priority patent/GB1024612A/en
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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
    • G03C5/00—Photographic processes or agents therefor; Regeneration of such processing agents
    • G03C5/26—Processes using silver-salt-containing photosensitive materials or agents therefor
    • G03C5/50—Reversal development; Contact processes

Definitions

  • This invention relates to photography, and more particularly, to photographic developers for use in reversal processing of photographic color films and papers.
  • multi-layer photographic elements used for color photography there are usually at least three selectively sensitive emulsion layers coated on a conventional photographic support, such as cellulose ester film, paper, polyvinyl resin film, polyester film, etc.
  • a conventional photographic support such as cellulose ester film, paper, polyvinyl resin film, polyester film, etc.
  • the uppermost silver halide emulsion layer may be bluesensitive, while the silver halide emulsion layer closest to the support may be red-sensitized.
  • a green sensitized silver halide emulsion layer there may be a green sensitized silver halide emulsion layer.
  • a yellow filter layer is used between the blue-sensitive and the green-sensitized silver halide emulsion layer.
  • additional silver halide emulsion layers, gelatin interlayers, and the like may also be present.
  • the silver halide emulsion layers may contain some of the processing ingredients, such as the color-forming compounds or couplers.
  • the photographic material is first processed to a conventional black-and-white silver negative in a developer which does not contain a developing agent capable of coupling with any of the color-forming compounds or couplers which may be present. Without removing unexposed silver halide, the material is given a reversal reexposure, followed by color development.
  • the technique of color reversal processing is well known to those skilled in the photographic art and color materials which can be used in such processing have been previously described in a number of domestic and foreign patents, such as Mannes et al. US. Patent 2,252,718, issued August 19, 1941.
  • the color materials useful in the present invention include those having silver halide emulsion layers containing the color-forming materials or couplers in a layer, or layers, as well as color materials intended for processing in a color developer which contains the color coupler.
  • cyclohexane compounds containing an amino radical and in addition to the amino radical, a polar substituent, such as hydroxyl, amino, hydroxyalkyl (hydroxyethyl, hydroxypropyl, etc.), etc.
  • Particularly useful cyclohexane compounds are those which contain an aminomethyl substituent.
  • Typical cyclohexane compounds useful in our invention comprise 1,4-bis(methylamino)cyclohexane, 4- aminocyclohexanol, 1-cyclohexaneamino-Z-propanol, etc.
  • cyclohexane compounds of our invention when used either in the black-and-white negative developer, or in one or more of the color developers, have adequate photographic activity and permit reasonable film speeds with very low fog density. They have low volatility, low toxicity, high water solubility and only a slight tendency to form carbamates under the alkaline conditions present in many of these photographic developers. In addition, when these cyclohexane compounds are employed in color developers, they show no tendency to reduce the sharpness of the color images.
  • the cyclohexane compounds used as silver halide solvents in our invention can be employed under rather wide concentration ranges, depending upon the type of silver halide developer, concentration of alkali, type of alkali, type of coupler, etc. In general, we have found that quite useful results are obtained in black-and-white silver halide negative developers if the concentration of the cyclohexane compound varies from about 0.5 to 10 grams per liter. Approximately the same concentration ranges for the cyclohexane compound can be employed in color developers, although we have found that especially good results are obtained within the range of about 1 to 8 grams per liter.
  • the cyclohexane compounds of our invention can be employed in a variety of aqueous alkaline solutions containing various photographic developing agents.
  • the black-and-white negative developing agents which have been found particularly useful in our invention comprise the dihydroxybenzenes, such as hydroquinone, toluquinone, etc., N-methyl-p-aminophenol salts, etc., or mixtures of such developing agents.
  • useful in the negative developers of our invention are the 3-pyrazolidones, such as 1-phenyl-3-pyrazolidone, 4,4-dimethyl-1- phenyl-3-pyrazolidone, etc.
  • Typical of r-forrning developers are the sulfonarnido substituted penylenediamines disclosed in Weissberger et al., US. Pa nt 2,548,574, issued April 10, 195]; the substituted p-p enylenediamines disclosed in Weissberger et al., US. Patent 2,566,271, issued August 28, 1951, etc.
  • the pH of the developers useful in our process can vary depending upon the particularv photographic material which is to be processed in the developers.
  • color developers it has been found that the cyclohexane compounds of our invention are outstanding at relatively high pH values, i.e., where the pH is at least 10.0 and as high as 11.5 to 12.5.
  • Our invention is primarily directed to the development of the ordinarily employed gelatino-silver-balide developing-out emulsions, e.g., gelatino-silver-chloride, -chlorobromide, -chioroiodide, -chiorobromiodide, -bromide, -bromiodide, etc. While the results illustrated below were obtained using gelatino-silver bromiodide emulsions, excellent results can be obtained using other silver halide emulsions. These emulsions can be coated in the usual manner on a suitable support, e.g.. glass, cellulose nitrate film, cellulose acetate film, polyvinyl film, polyester film, paper, metal, etc.
  • a suitable support e.g. glass, cellulose nitrate film, cellulose acetate film, polyvinyl film, polyester film, paper, metal, etc.
  • Photographic silver halide emulsions useful in our iuverition can also contain such addenda as chemical sensitizers, e.g.. sulfur sensitizers (e.g., allyl thiocarbarnide, thiourea. allyl isothiocyanate, cystine, etc), various gold compounds (eg. potassium chloroaurate, auric trichloride, etc.) (see US. Patents 2,540,085; 2,597,856 and 2,597,915), various azaindene compounds (such as those disclosed in US. Patent 2,716,062), condensation prodcol nets of alkylene oxides, such as those shown in US. Patent 2,400,532, as well as the additives mentioned in Jones et al.,'U.S. Patent 2,937,089.
  • chemical sensitizers e.g., sulfur sensitizers (e.g., allyl thiocarbarnide, thiourea. allyl isothi
  • ypical color-forming compounds or couplers which areuseful in color photography, according to our inventior t, include the following:
  • amylsulfanilide Z-cyanoacetylcoumarone-S-sulfon-N-n-butylanilide
  • Z-cyanoacetyl-S -benzoylamino-coumarone 2-cyanoacetylcoumarone-S-sulfonclimethylamide
  • amylsulfonanilide 1-p-laurylphenyl-3-methyl-5-pyrazolonc 1-B-naphthyl-B-amyl-S-pyrazolone l-p-nitrophenyl-3 -n-amyl-5-pyrazolone 1-pphenoxyphenyl-3-n-amyl-5-pyrazolone 1- henyl-3 -namyl-5-pyrazolone 1,4-phenylene bis-3-( l-phenyl-S-pyrazolone) 1 -phenyl-3-acctylamino-5 -pyrazolone 1-phenyl-3 -propionylamino-5-pyrazolone 1-phenyl-3 -n-valerylamino-5 -pyrazolone 1-phenyl-3-chloroacetylamino-S-pyrazolone 1-phenyl-3 -d ichl oro acetylamino-S-pyrazolone 1-phenyl-3 -benz
  • amylacetanilide N,N'-di(w-benzoylacetyl)-p-phenylenediamine N,N'-di-(acetoacetamino)diphenyl Z-methoxyacetanilide a- ⁇ 3- a- (2,4-di-tert.-amylphenoxy) acetam1do]benzoyl sions of our invention include those described in Spenceand Carroll US. Patent 2,640,776, issued June 2, 1953;
  • Example 1 A portion 'ofa gelatino-silver-bromiodide emulsion which had been sensitized with a sulfur compound and a gold salt as mentioned-above, was'coated on a cellulose acetate support and dried.- The. coating was then cut into ,several strips and one strip of each was then exposed for second to'a 500w att, 3000 K. light source on an Eastman Type II sensitomcter. One of the exposed strips was then developed for 3 minutes in adeveloper having the following composition;
  • the strip was then washed for about 2 minutes in .Water and ;then given a reversal exposure for about 10 seconds (flash) with a No. 2 Photoflood set at a distance of about 60 inches.
  • the strip was then developed for approximately minutes in a developer having the following formula:
  • the strip was then treated for about 2 minutes in a fixing bath having the following composition:
  • Thei strip was then washed in water and dried.
  • the processed strip showed good definition and speed.
  • Example 2 A multi-layer photographic element of the type described in Mannes et al. US. Patent 2,252,718, issued August 19, 1941, was exposed to an original multi-colored scene and developed for about 3% minutes at 80 F. in a developer having the following composition:
  • the photographic element was then spray washed with Water for about 30 seconds and exposed to red illumination of about 1100 ft. candle seconds.
  • the exposed material was then developed in a cyan developer having the following formula:
  • the photographic element was then washed for about 30 seconds with water and exposed to blue light of 300 ft. candle seconds intensity and developed in a yellow colorproducing developer containing a phenylenediamine color developing agent, such as 4-amino-N,N-diethylaniline hydrochloride and a yellow coupler, such as Coupler No. 47 from column 4 of US. Patent 2,956,876.
  • a phenylenediamine color developing agent such as 4-amino-N,N-diethylaniline hydrochloride and a yellow coupler, such as Coupler No. 47 from column 4 of US. Patent 2,956,876.
  • the photographic element was then washed and fogged chemically by treatment with a sodium borohydride solution.
  • the photographic element was then developed in a magenta color developer containing a color-developing agent, such as that used in Example 1 above and a magenta coupler, such as Coupler No. 30 in column 4 of U.S. Patent 2,956,876.
  • the photographic element was then bleached, fixed and dried as described in Example 1.
  • Example 3 Example 2 was repeated using a negative developer containing 6.0 grams per liter of l-cyclohexylamino-Z- propanol in place of the 4-aminoeyclohexanol used in Example 2. Again, there was a substantial increase in speed compared to material processed in a negative developer containing isopropylamine as the silver halide solvent.
  • a photographic developing composition consisting of an aqueous alkaline solution comprising a photographic developing agent and a silver halide solvent comprising a cyclohexane containing an amino radical attached to the carbocyclic ring thereof and in addition to saidamino radical, a polar substituent selected from the class consisting of an amino radical, a hydroxyalkyl radical.
  • a photographic of an aqueous alkaline solution comprising a photographic developing agent and 1,'4-bis(methylamino)cyclohexane.
  • a photographic developing composition consisting of an aqueous alkaline solution comprising a photographic developing agent and 4-aminocyclohexanol.
  • a photographic developing composition consisting of an aquoeus alkaline solution comprising at least one photographic developing agent selected from the class consisting ofv 3-pyrazolidones, dihydroxyben zenes and p-N- hydroxyl radical and a a developing borhfioiiidii consisting" 12.
  • methylaminophenol salts and a'silver halide solvent com-- prising a cyclohexane containing an amino radical attached to the carbocyclic ring thereof and in addition to said amino radical, a polar substituent'selected from the class consisting of an amino radical, a hydroxyl radical and a hydroxyalkyl radical.
  • a photographic developing composition consisting of an aqueous alkaline solution comprising at least one photographic silver halide developing agent selected from the class consisting of 3-pyrazolidones, dihydroxybenzenes and p-N-methylaminophenol salts, and 1,4-bis(methylamino)cyclohexane.
  • a photographic developing composition consisting of an aqueous alkaline solution comprising at least one photographic silver halide developing agent selected from the class consisting of 3-pyrazolidones, dihydroxybenzenes and p-N-methylaminophenol salts, and 4-aminocyclohexanol.
  • a photographic developing composition consisting of an aqueous alkaline solution comprising at least one photographic silver halide developing agent selected from the class consisting of 3-pyrazolidones, dihydroxybenzenes and p-N-methylaminophenol salts, and l-cyclohexylamino-2-propanol.
  • a photographic developing composition consisting of an aqueous alkaline solution comprising a phenylenediamine photographic silver halide developing agent and a silver halide solvent comprising a cyclohexane containing an amino radical attached to the carbocyclic ring thereof and in addition to said amino radical, a polar substituent selected from the class consisting of an amino radical, a hydroxyl radical and a hydroxyalkyl radical.
  • a photographic developing composition consisting of an aqueous alkaline solution comprising a p-N-phenylenediamine photographic silver halide developing agent and 1,4-bis(methylamino)cyclohexane.
  • a photographic developing composition consisting of an aqueous alkaline solution comprising a p-phenylenediamine photographic silver halide developing agent and -1-cyclohexylamino-2-propanol.
  • compositions a silverhalide solvent comprising a cyclohexane containing an amino radical attached to the carbocyclic ring thereof and in addition to said amino radical, a polar substituent selected from the class consisting of an amino radical, a hydroxyl rad ical and a hydroxyalkyl I radical.
  • a process according to claim 17 wherein said silver halide solvent is 1-cyclohexylamino-2-propanol.

Description

United States Patent New Jersey No Drawing. Filed Oct. 23, 1961, Ser. No. 147,055
20 Claims. (Cl. 9661) This invention relates to photography, and more particularly, to photographic developers for use in reversal processing of photographic color films and papers.
In multi-layer photographic elements used for color photography, there are usually at least three selectively sensitive emulsion layers coated on a conventional photographic support, such as cellulose ester film, paper, polyvinyl resin film, polyester film, etc. For example, the uppermost silver halide emulsion layer may be bluesensitive, while the silver halide emulsion layer closest to the support may be red-sensitized. Between these two emulsion layers, there may be a green sensitized silver halide emulsion layer. Frequently, a yellow filter layer is used between the blue-sensitive and the green-sensitized silver halide emulsion layer. Of course, additional silver halide emulsion layers, gelatin interlayers, and the like, may also be present. The silver halide emulsion layers may contain some of the processing ingredients, such as the color-forming compounds or couplers. In processing multi-layer color materials of the type useful in our invention, the photographic material is first processed to a conventional black-and-white silver negative in a developer which does not contain a developing agent capable of coupling with any of the color-forming compounds or couplers which may be present. Without removing unexposed silver halide, the material is given a reversal reexposure, followed by color development. The technique of color reversal processing is well known to those skilled in the photographic art and color materials which can be used in such processing have been previously described in a number of domestic and foreign patents, such as Mannes et al. US. Patent 2,252,718, issued August 19, 1941.
The color materials useful in the present invention include those having silver halide emulsion layers containing the color-forming materials or couplers in a layer, or layers, as well as color materials intended for processing in a color developer which contains the color coupler.
3,128,182 Patented Apr. 7, 1964 them have the added disadvantage of reducing the defini- It is, therefore, an object of our invention to provide improved developers for reversal color photography. Another object is to provide a method of processing reversal color materials using the improved developers of our invention. Other objects will become apparent from a consideration of the following description and examples. In the processing of various photographic materials, it has been rather common to employ silver halide solvents in the photographic silver halide developing compositions for the purpose of accelerating either black-andwhite or color development. However, some of the amines which have been previously used in the developing compositions of photographic color materials have been found to be highly toxic and quite volatile. In addition, some of these amines readily form carbamates in the photographic developers commonly used and some of tion of the colored images formed in certain of the sensitized layers, particularly the green-sensitized layer which develops into a magenta image. Some of these amines also interfere with development so that development does not proceed to the production of an image of desired density.
While some amines have useful properties for specific types of photographic developers, such properties are usually unique and limited to the use of a particular set of conditions. These amine silver halide solvents when used in the black-and-white developers will affect the curve shapes of all sensitized layers as well as affecting the overall speed and fog, while in a color developer, the curve shape of the layer being developed is primarily affected, as well as the covering power of the resulting dye, silver/dye ratio, and the sharpness of the dye image. The activity of certain of the silver halide solvents, such as isopropylamine, particularly in the black-and-whitedeveloper, is lower where the alkaline material is an alkali metal carbonate, since such silver halide solvents readily form carbamates with the carbonate, resulting in a serious loss of the silver halide solvent.
We have now found that the afore-mentioned difficulties in the black-and-white developing solutions, as well as the color developing solutions, can be entirely or large ly overcome by using as silver halide solvents, cyclohexane compounds containing an amino radical, and in addition to the amino radical, a polar substituent, such as hydroxyl, amino, hydroxyalkyl (hydroxyethyl, hydroxypropyl, etc.), etc. Particularly useful cyclohexane compounds are those which contain an aminomethyl substituent. Typical cyclohexane compounds useful in our invention comprise 1,4-bis(methylamino)cyclohexane, 4- aminocyclohexanol, 1-cyclohexaneamino-Z-propanol, etc.
It has been found that the cyclohexane compounds of our invention, when used either in the black-and-white negative developer, or in one or more of the color developers, have adequate photographic activity and permit reasonable film speeds with very low fog density. They have low volatility, low toxicity, high water solubility and only a slight tendency to form carbamates under the alkaline conditions present in many of these photographic developers. In addition, when these cyclohexane compounds are employed in color developers, they show no tendency to reduce the sharpness of the color images.
The cyclohexane compounds used as silver halide solvents in our invention can be employed under rather wide concentration ranges, depending upon the type of silver halide developer, concentration of alkali, type of alkali, type of coupler, etc. In general, we have found that quite useful results are obtained in black-and-white silver halide negative developers if the concentration of the cyclohexane compound varies from about 0.5 to 10 grams per liter. Approximately the same concentration ranges for the cyclohexane compound can be employed in color developers, although we have found that especially good results are obtained within the range of about 1 to 8 grams per liter.
The cyclohexane compounds of our invention can be employed in a variety of aqueous alkaline solutions containing various photographic developing agents. The black-and-white negative developing agents which have been found particularly useful in our invention comprise the dihydroxybenzenes, such as hydroquinone, toluquinone, etc., N-methyl-p-aminophenol salts, etc., or mixtures of such developing agents. Also, useful in the negative developers of our invention are the 3-pyrazolidones, such as 1-phenyl-3-pyrazolidone, 4,4-dimethyl-1- phenyl-3-pyrazolidone, etc.
Any of the conventional color-forming developing agents which have been previously described in the prior art can be used in our invention. The color-forming developers or developing agents which have been found to be especially useful in our invention include aromatic primary amines containing an amino (substituted or not) or iiydroxyl substituent. Phenylenediamines and substitut-d derivatives thereof containing a primary amino gr p are especially useful in our invention. Typical of r-forrning developers are the sulfonarnido substituted penylenediamines disclosed in Weissberger et al., US. Pa nt 2,548,574, issued April 10, 195]; the substituted p-p enylenediamines disclosed in Weissberger et al., US. Patent 2,566,271, issued August 28, 1951, etc.
The pH of the developers useful in our process, including both the color developers and the black-and-whitc negative developers, can vary depending upon the particularv photographic material which is to be processed in the developers. In the case of color developers, it has been found that the cyclohexane compounds of our invention are outstanding at relatively high pH values, i.e., where the pH is at least 10.0 and as high as 11.5 to 12.5.
Our invention is primarily directed to the development of the ordinarily employed gelatino-silver-balide developing-out emulsions, e.g., gelatino-silver-chloride, -chlorobromide, -chioroiodide, -chiorobromiodide, -bromide, -bromiodide, etc. While the results illustrated below were obtained using gelatino-silver bromiodide emulsions, excellent results can be obtained using other silver halide emulsions. These emulsions can be coated in the usual manner on a suitable support, e.g.. glass, cellulose nitrate film, cellulose acetate film, polyvinyl film, polyester film, paper, metal, etc.
Photographic silver halide emulsions useful in our iuverition can also contain such addenda as chemical sensitizers, e.g.. sulfur sensitizers (e.g., allyl thiocarbarnide, thiourea. allyl isothiocyanate, cystine, etc), various gold compounds (eg. potassium chloroaurate, auric trichloride, etc.) (see US. Patents 2,540,085; 2,597,856 and 2,597,915), various azaindene compounds (such as those disclosed in US. Patent 2,716,062), condensation prodcol nets of alkylene oxides, such as those shown in US. Patent 2,400,532, as well as the additives mentioned in Jones et al.,'U.S. Patent 2,937,089.
ypical color-forming compounds or couplers which areuseful in color photography, according to our inventior t, include the following:
l COUPLERS PRODUCING CYAN IMAGES 5- (p-amylphenoxybenze nesulfonamino) l -naphthol 5- N-benzyl-N naphtha]enesulfonamino l -naphthol 5-(n-benzyl-N-n-valerylamino)-1-naphthol S-caproy] amino- 1 -naphthol Z-chloro-S-(N-n -valcrylN-pisopropylbenzylamino) -1- naph thol 2,4-dichloro-5- (p -n itrobenzoyl-fi-o-hydroxyethylamino) l-naphth ol 12,4-Qdichloro-5-palmitylamino-Lnaphthol 2,2-dihydroxy-5 ,5 ditvromostilbenc S-diphcnylethcrsniionamido-l-naphthol l-hyd roxy ZtN-isoa m3- l-N-phenyl napb tha mide l.-hydroxy-2-( N-psec amylphenyl) naphthamide X-hydroxyl -a-naphtho vl-1,2,3,4-tetrahydroquinoline 2-lauryl-4-chloro phenol l-naphthol-2-carboxyiicu-11aphthalidc 1-naphthol-5-sul fo-cycloh exy l n mide 5 -phenoxyacetam ino-l-napint S-B-phenylpropionylamino-i; 'thol Monochlor-S-(N-y-phcnylpr :j g" -psec.-amylbenzoylamino) -1-naphthol 2-acetylamino-5-methylphenol 2-benzoylamino-3,S-dimethylpb-s 6- {'y-{ 4- ['y- 2,4-di-tert. amy lp utyramido1phenoxy} acetamido}-2,4-dichloro iylphenol l-hydroxy-Z- 5- 2,4-di-t ert. amylpr' 1oxy)-n-butyl]naphthamide 2-ct(p-tert. amylphenoxy) n butyi' 'ii no-S-methylphenol nino-4-chloro-5- ntethylphenol Z-(tf-tert. amylphenoxy-p-bcnz yl no-4-chl0ro-5- methylphenol 2-(4--tert.amyl-3'-phenoxybenzoyl.- 5 -3,5-dimethyll'phenol phenol 2-(4-tert. amyl-3-phenoxybenzoylamino) -3-meth vl-lphenol 2-(4-tert. amyl-3'-phenoxybenzoylamino)--6-1neihyl-1- phenol 2-(4"-tert. amyl-3 '-phenoxybenzoyl amino -3,6-diniethylphenol 2,6-di(4"-tert. amyl 3-p'hcnoxybcnzoylaminc)-l-phcnol 2-a (4'-tert. amylphenoxy)butyrylamino-i phenol 2-(o-acetarnido-fi-phenylcthyl)-l-hydroxynaphthamide 2(4-tert. amyl-3--phenoxybenzoylamino)QLS-dimethyll-phenol 2-[a-(4-tert. amylphenoxy)-nbutyrylammold-methyllphenol 2(4-tert. amyl-3'-phcnoxybenzoylamino)-4-chloro' iphenol 3-[ x-(4'-tert. amylphcnory)-n-lmtyrylamino]-6-chlorophenol 3-(4"-tert. amyl-3-phenoxybenzoylamino) phenol 3-la-(4'-tert. amylphenoxy)-n-butyrylumino}-5-chlorophenol 3-{a-(4-tert. amylphenoxy)--n-butyrylamino}-Zchlorophenol I 2-a-(4'-tert. an'iylphenoxybutyryiamino)-5-chlorophcnol 2-(4-tert. amyl-B'-phenoxybenzoyiamino)-3-chlorophenol S-benzene sulfonaminodmaphthol 2,4-dichloro-5-bcnzcnesnliimamino-lmapbthol 2,4-dichloro-5- (p-tolucnesulfonaminohl -naphthoi 5-( l,2,3,4-tetrahydronaphthalencfi-sullaminn t-l-naphti'toi 2,4-dichloro-5-(4'-br0modiphcnyl-4-sullonamino)--lnaphthol 5-(quinolinc-S-sulfamino)-Lnaphthol Any of the acylaminophenol couplers disclosed in Sal- NlIC o-dn-o-Qonn C II etc.
COUPLERS PRODUCING MAGENTA IMAGES l-p-sec. amylphenyl-3-n-amyl-5-pyrazolone 2-cyanoacetyl-5-(p-sec. amylbenzoylamino)coumarone Z-cyanoacetylcoumarone-S- (n-amyl-p-sec. amylsulfanilide) 2-cyanoacctylcoumarone-S- (N-n-amyl-p-tert. amylsulfanilide) Z-cyanoacetylcoumarone-S-sulfon-N-n-butylanilide Z-cyanoacetyl-S -benzoylamino-coumarone 2-cyanoacetylcoumarone-S-sulfonclimethylamide Z-cyanoacetylcoumarone-5-sulfon-N-methylanilide 2-cyanoacetylnaphthalene sulfon-N-methylanilide 2-cyanoacctylcoumarone5 -(N-y-phenylpropyl)-p-tert.
amylsulfonanilide 1-p-laurylphenyl-3-methyl-5-pyrazolonc 1-B-naphthyl-B-amyl-S-pyrazolone l-p-nitrophenyl-3 -n-amyl-5-pyrazolone 1-pphenoxyphenyl-3-n-amyl-5-pyrazolone 1- henyl-3 -namyl-5-pyrazolone 1,4-phenylene bis-3-( l-phenyl-S-pyrazolone) 1 -phenyl-3-acctylamino-5 -pyrazolone 1-phenyl-3 -propionylamino-5-pyrazolone 1-phenyl-3 -n-valerylamino-5 -pyrazolone 1-phenyl-3-chloroacetylamino-S-pyrazolone 1-phenyl-3 -d ichl oro acetylamino-S-pyrazolone 1-phenyl-3 -benzoylamino-5-pyrazolone l-phcnyl-3- m-aminobenzoyl) amino-S-pyrazolone l-phenyl-S-(p-sec. amylbenzoylamino)-5-pyrazolone l-phenyl-3 -diamylbenzoylamino-S-pyrazolone l -phenyl-3 B-naphthoylamino-S-pyrazolone 1-phcnyl-3-ph enylcarbamylamino-S-pyrazolone 1-phenyl-3-palmitylamino-S-pyrazolone 1 -ph enyl-3 -henzenesulfonylamino-S-pyrazolone 1-(p-phenoxyphcnyl)-3-(p-tcrt. amyloxybenzoyl)amino- 5- pyrazolone 1- (2',4,6-tribromophenyl -3-benzamido-5-pyrazolone 1-( 2,4,6'-trichlorophenyl '-3-benzamido-5-pyrazolone l-(2',4',6'-trichlorophenyl)-3-phenylacetamido-5-pyrazolone l-( 2',4',6-tribromophenyl -3 -phenylacetamido-5-pyrazolone 1- 2,4'-dichlorophenyl -3- 3 2"',4"'-di-tert. a ylphenoxyacetamido)benzamido] -5-pyrazolone I l- (2,4',6'-trichl orophenyl -3- 3 (2",4"-di-tert. amylv phenoxyacetamido benzamido] -5 pyrazolone 1-( 2,4',6-tribromophenyl -3- 3 2',4'-di-tert. amylphenoxyacetamido benzamido] -5-pyrazolone l- 2',4',6'-trichl0rophenyl -3- B- (2"',4"'-di-tert. amylphenoxy -propionamido] -5-pyrazolone 1-(2,4,6-tribromophenyl)-3-[p-(2"',4"'-di-tert. amy1 phenoxy) -propionamido] -5-pyrazolone amido]-5-pyrazolone 1-(2',4',6' trichlorophenyl.).-3-(4-nitroanilino)-5Ppyrazolone COUPLERS "PRODUCING. YELLOW IMAGES N-amyl-p-benzoylacetaminobenzenesulfonate N-(4-anisoylacetaminobenzenesulfonyl -N.-benzy1-mtoluidine N- (4-benzoylacetaminobenzenesulfonyl) -N-benzyl-mtoluidine 1 N-(4-benzoylacetaminobenzenesulfonyl)-N-n-amyl-p-= toluidine N-(4-benzoylacetaminobenzenesulfonyl)-N-benzvlaniline w- (p-Benzoylbenzoyl acetanilide w-Benzoylacet-2,S-dichloroanilide w-Benzoyl-p-sec. amylacetanilide N,N'-di(w-benzoylacetyl)-p-phenylenediamine N,N'-di-(acetoacetamino)diphenyl Z-methoxyacetanilide a-{3- a- (2,4-di-tert.-amylphenoxy) acetam1do]benzoyl sions of our invention include those described in Spenceand Carroll US. Patent 2,640,776, issued June 2, 1953;
Weissbergcr et al. US. Patent 2,407,210, issued September 3, 1946, and Weissberger et al. US. Patent 2,474,293, issued June 28, 1959..
The following examples will serve to illustrate the manner of practicing our invention.
Example 1 A portion 'ofa gelatino-silver-bromiodide emulsion which had been sensitized with a sulfur compound and a gold salt as mentioned-above, was'coated on a cellulose acetate support and dried.- The. coating was then cut into ,several strips and one strip of each was then exposed for second to'a 500w att, 3000 K. light source on an Eastman Type II sensitomcter. One of the exposed strips was then developed for 3 minutes in adeveloper having the following composition;
Sodium hexametaphosphate g 0.4 Sodium 'sulfite (anhydrous) g' 40.0 N-methyl-p-aminophenolsulfate y g 5.0 Hydroquinone g 2.0 Sodium carbonate (monohydrate') g 25.0 Potassium bromide g 1.0 Potassium iodide (0.l% solution) ccs 2 Water to make one liter. (pl-I was 10.1 at70 F.)
The strip was then washed for about 2 minutes in .Water and ;then given a reversal exposure for about 10 seconds (flash) with a No. 2 Photoflood set at a distance of about 60 inches. The strip was then developed for approximately minutes in a developer having the following formula:
Sodium hexametaphosphate g 1.0 Sodium sulfite (anhydrous) g 30 Sodium sulfate g 30 Sodi'um bromide g 0.5 Potassium iodide (0.1% solution) ccs 5 1,4-bis aminomcth yl cyclohexane -g- 5 Coupler 1 g 0.85 Sodfum hydroxide g 3 Col r developer g 3 Hy oxylamine sulfate g 0.35 Wa r to make 1 liter. (p at 80 F. was 12.40.) v
1 (2,4,6-trichlorophenyl) 3 [ll-(4 nitrophenoxy)- acct niido]5-p vrazolone.
2 amino-N,N-diethyl-3-methylaniliue hydrochloride. The, strip was then washed for about minutes in water andtreated for about 2 mintues in a silver bleach bath having the following composition:
, G. Potassium ferricyanide 100 Potassium bromide 10 Borax n 7.5 Boric acid 5.0 Water to make 1 liter.
The strip was then treated for about 2 minutes in a fixing bath having the following composition:
1 Ga Sodium thiosulfate (pentahydrate) 200 Sodium sulfite (anhydrous) 10 Water to make 1 liter.
Thei strip was then washed in water and dried. The processed strip showed good definition and speed.
In order to show that the cyclohexane compounds of ourlinvention are unique in photographic developers, one of the exposed strips was processed in a manner identical to that illustrated in the above example, except that the cyclohexane compound was omitted from the color developer. The strip processed in the color developer containing the cyclohexane compound had a D-max. difference of only -.14 compared to the control strip. On the other hand, when one of the exposed strips of Example 1 was processed as described in that example, except that cyclohexylamine was used in place of the 1,4-bis(methylamiho)cyclohexane in the color developer, there was a magenta D-max. difference of .48 compared to the control. These results can be summarized as follows.
AD-max.
E Addenda-Color developer: from control I Control Cyclohexylamine .48 1,4-bis(methylamino)cyclohexane .14
7 Example 2 A multi-layer photographic element of the type described in Mannes et al. US. Patent 2,252,718, issued August 19, 1941, was exposed to an original multi-colored scene and developed for about 3% minutes at 80 F. in a developer having the following composition:
The photographic element was then spray washed with Water for about 30 seconds and exposed to red illumination of about 1100 ft. candle seconds. The exposed material was then developed in a cyan developer having the following formula:
Water to one liter.
1 Sodium tetraphosphate.
'- As hydrochloride.
3 2-(o-acetamido-B-phenylethyl)-l-hydroxynaphthamidc.
The photographic element was then washed for about 30 seconds with water and exposed to blue light of 300 ft. candle seconds intensity and developed in a yellow colorproducing developer containing a phenylenediamine color developing agent, such as 4-amino-N,N-diethylaniline hydrochloride and a yellow coupler, such as Coupler No. 47 from column 4 of US. Patent 2,956,876. The photographic element was then washed and fogged chemically by treatment with a sodium borohydride solution. The photographic element was then developed in a magenta color developer containing a color-developing agent, such as that used in Example 1 above and a magenta coupler, such as Coupler No. 30 in column 4 of U.S. Patent 2,956,876.
The photographic element was then bleached, fixed and dried as described in Example 1.
As compared with a photographic element which had been similarly processed using a negative developer containing 6.5 grams per liter of isopropylamine. it was noted that there was a substantial speed increase for the material processed in the 4-aminocyelohexanol (approximately /2 stop), that there was a relatively small loss -in reversal D-max. (0.15 unit) and that there was an increase in the speed/fog ratio compared to the material processed in the developer containing the isopropylamine. In order to produce a material processed in a negative developer containing isopropylamine and provide a speed comparable to material processed in the 4-aminocyclo hexanol-containing developer, it was found necessary to increase the isopropylamine concentration to such an extent that the D-max. of the resulting image was materially reduced in all layers of the elements.
Example 3 Example 2 was repeated using a negative developer containing 6.0 grams per liter of l-cyclohexylamino-Z- propanol in place of the 4-aminoeyclohexanol used in Example 2. Again, there was a substantial increase in speed compared to material processed in a negative developer containing isopropylamine as the silver halide solvent.
The invention has been described in detail with particular reference to preferred embodiments thereof, but it will be understood that variations and modifications can be effected within the spirit and scope of the invention as described hereinabove and as defined in the appended claims.
What We claim as our invention and desire secured by Letters Patent of the United States is: I
1. A photographic developing composition consisting of an aqueous alkaline solution comprising a photographic developing agent and a silver halide solvent comprising a cyclohexane containing an amino radical attached to the carbocyclic ring thereof and in addition to saidamino radical, a polar substituent selected from the class consisting of an amino radical, a hydroxyalkyl radical.
2. A photographic of an aqueous alkaline solution comprising a photographic developing agent and 1,'4-bis(methylamino)cyclohexane.
3. A photographic developing composition consisting of an aqueous alkaline solution comprising a photographic developing agent and 4-aminocyclohexanol.
4. A photographic developing composition consisting of an aqueous alkaline solution comprising, a photographic developing agent and 1-cyclohexylamino-2=propanol.
5. A photographic developing composition consisting of an aquoeus alkaline solution comprising at least one photographic developing agent selected from the class consisting ofv 3-pyrazolidones, dihydroxyben zenes and p-N- hydroxyl radical and a a developing borhfioiiidii consisting" 12. A photographic developing composi on as defined 'inplair'ir 11 wherein said aqueous alkaline solution con- I 'halide-developingagentto produce a colored image.
methylaminophenol salts, and a'silver halide solvent com-- prising a cyclohexane containing an amino radical attached to the carbocyclic ring thereof and in addition to said amino radical, a polar substituent'selected from the class consisting of an amino radical, a hydroxyl radical and a hydroxyalkyl radical.
6. A photographic developing composition consisting of an aqueous alkaline solution comprising at least one photographic silver halide developing agent selected from the class consisting of 3-pyrazolidones, dihydroxybenzenes and p-N-methylaminophenol salts, and 1,4-bis(methylamino)cyclohexane.
7. A photographic developing composition consisting of an aqueous alkaline solution comprising at least one photographic silver halide developing agent selected from the class consisting of 3-pyrazolidones, dihydroxybenzenes and p-N-methylaminophenol salts, and 4-aminocyclohexanol.
8.'A photographic developing composition consisting of an aqueous alkaline solution comprising at least one photographic silver halide developing agent selected from the class consisting of 3-pyrazolidones, dihydroxybenzenes and p-N-methylaminophenol salts, and l-cyclohexylamino-2-propanol.
9. A photographic developing composition consisting of an aqueous alkaline solution comprising a phenylenediamine photographic silver halide developing agent and a silver halide solvent comprising a cyclohexane containing an amino radical attached to the carbocyclic ring thereof and in addition to said amino radical, a polar substituent selected from the class consisting of an amino radical, a hydroxyl radical and a hydroxyalkyl radical.
10. A photographic developing composition as defined in claim 9 wherein said aqueous alkaline solution contains a color-forming compound capable of coupling with the oxidation products of said phenylenediamine silver halide developing agent to produce a colored image.
11. A photographic developing composition consisting of an aqueous alkaline solution comprising a p-N-phenylenediamine photographic silver halide developing agent and 1,4-bis(methylamino)cyclohexane.
15. A photographic developing composition consisting of an aqueous alkaline solution comprising a p-phenylenediamine photographic silver halide developing agent and -1-cyclohexylamino-2-propanol. I
16. A photographic developing composition as defined in claim 15 wherein said aqueous alkaline solution contains a color-forming compoundcapable of couplingwith the oxidation products "ofsaid"p-phenylenediamine silver halide developing agent to produce a colored image.
17. In the reversal process of color photography for producing a colored image in a photoexposed multilayer color material having sensitivity in discrete areas thereof in the red, green and blue regions, respectifv I of the visible spectrum, by first developing a black-andwhite negative image, followed by at least one development in a color developer to produce a color record, the step of incorporating in at least one of the developing,
compositions a silverhalide solvent comprising a cyclohexane containing an amino radical attached to the carbocyclic ring thereof and in addition to said amino radical, a polar substituent selected from the class consisting of an amino radical, a hydroxyl rad ical and a hydroxyalkyl I radical.
18. A process according to claim 17 wherein said sil 19. A process according to claim 17 wherein said silver halide solvent is 4-aminocyelohexanol.
20. A process according to claim 17 wherein said silver halide solvent is 1-cyclohexylamino-2-propanol.
References Cited in the file this patent UNITED STATES PATENTS 2,306,923 Wood Dec. 29, 1942 2,857,276 Land et al. Oct. 21, 1958 3,004,850 Dickinson et al. ...2 Oct. 17, 1961 FOREIGN PATENTS OTHER-REFERENCES Germany Ian. 5, 1955 UNITED STATES PATENT OFFICE CERTIFICATE OF CORRECTION Patent No. 3, 128,182 April 7, 1964 Charlton c. Bard et a1,
' It is hereby certified that error appears in the above numbered patent 'req'liring correction and that the said Letters Patent should read as corrected below.
Column 9, line 56, for "p-Nphenyl" read p-phenyl- Signed and sealed this 4th day of August 1964.
' (SEAL) A ttestf ERNEST w. SWIDER EDWARD J. BRENNER Atmsting Officer Commissioner of Patents

Claims (2)

1. A PHOTOGRAPHIC DEVELOPING COMPOSITION CONSISTING OF AN AQUEOUS ALKALINE SOLUTION COMPRISING A PHOTOGRAPHIC DEVELOPING AGENT AND A SILVER HALIDE SOLVENT COMPRISING A CYCLOHEXANE CONTAINING AN AMINO RADICAL ATTACHED TO THE CARBOCYCLIC RING THEREOF AND IN ADDITION TO SAID AMINO RADICAL, A POLAR SUBSTITUENT SELECTED FROM THE CLASS CONSISTING OF AN AMINO RADICAL, A HYDROXYL RADICAL AND A HYDROXYALKYL RADICAL.
6. A PHOTOGRAPHIC DEVELOPING COMPOSITION CONSISTING OF AN AQUEOUS ALKALINE SOLUTION COMPRISING AT LEAST ONE PHOTOGRAPHIC SILVER HALIDE DEVELOPING AGENT SELECTED FROM THE CLASS CONSISTING OF 3-PYRAZOLIDONES, DIHYDROXYBENZENES AND P-N-METHYLAMINOPHENOL SALTS, AND 1,4-BIS(METHYLAMINO)-CYCLOHEXANE.
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FR912638A FR1336560A (en) 1961-10-23 1962-10-18 New developer for color photography
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US3352884A (en) * 1964-03-20 1967-11-14 Upjohn Co 1-benzenesulfonyl-3-(oxocycloalkyl)-ureas and the cyclic alkylene ketals thereof
US3960569A (en) * 1973-11-20 1976-06-01 Fuji Photo Film Co., Ltd. Diffusion transfer color film unit with hydroxy substituted alkylene amino development accelerators
US4030920A (en) * 1976-04-12 1977-06-21 Eastman Kodak Company Processing compositions containing glycols for color transfer processes comprising direct positive silver halide developement
US4076531A (en) * 1975-07-30 1978-02-28 E. I. Du Pont De Nemours And Company Image anchorage in photographic films
US4264717A (en) * 1978-10-21 1981-04-28 Agfa-Gevaert, A.G. Color photographic material and color photographic processes
EP0266797A2 (en) 1986-11-07 1988-05-11 Fuji Photo Film Co., Ltd. Method of processing silver halide color photographic material and photographic color developing composition
EP0452886A2 (en) 1990-04-17 1991-10-23 Fuji Photo Film Co., Ltd. Method of processing a silver halide color photographic material
US5310633A (en) * 1992-05-13 1994-05-10 Fuji Photo Film Co., Ltd. Bleach-fixing composition for color photographic material and method for processing a color photographic material with the same
US5362610A (en) * 1991-10-28 1994-11-08 Konica Corporation Photographic processing agent
US5366853A (en) * 1991-11-06 1994-11-22 Konica Corporation Tablet-shaped processing agent and method for processing silver halide photographic light sensitive materials
EP0631185A1 (en) 1993-06-11 1994-12-28 Fuji Photo Film Co., Ltd. Method for continuously processing silver halide color photosensitive material
US5409805A (en) * 1993-07-29 1995-04-25 Konica Corporation Solid processing agent for silver halide photographic light-sensitive materials
US5452045A (en) * 1992-10-30 1995-09-19 Konica Corporation Apparatus for processing a light-sensitive silver halide photographic material
EP0686875A1 (en) 1994-06-09 1995-12-13 Fuji Photo Film Co., Ltd. Method of processing silver halide color photographic materials
EP0720049A2 (en) 1990-05-09 1996-07-03 Fuji Photo Film Co., Ltd. Photographic processing composition and processing method using the same
US5576161A (en) * 1994-08-12 1996-11-19 Konica Corporation Silver halide light-sensitive photographic material and method of processing thereof
US5766830A (en) * 1994-09-09 1998-06-16 Konica Corporation Photographic processing method for processing a silver halide photographic light-sensitive material

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DE923891C (en) * 1952-05-06 1955-02-21 Agfa Ag Fuer Photofabrikation Process for developing photographic silver halide emulsions
US2857276A (en) * 1954-11-23 1958-10-21 Polaroid Corp Photographic processes and compositions useful therein
US3004850A (en) * 1958-11-28 1961-10-17 Ilford Ltd Production of positive photographic records

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US2531832A (en) * 1947-06-12 1950-11-28 Du Pont Silver halide developers containing polyethylene glycols
US2618558A (en) * 1949-04-12 1952-11-18 Eastman Kodak Co Photographic developers comprising an n,n - dialkyl-p-phenylenediamine and a benzenesulfonate
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US2857276A (en) * 1954-11-23 1958-10-21 Polaroid Corp Photographic processes and compositions useful therein
US3004850A (en) * 1958-11-28 1961-10-17 Ilford Ltd Production of positive photographic records

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3352884A (en) * 1964-03-20 1967-11-14 Upjohn Co 1-benzenesulfonyl-3-(oxocycloalkyl)-ureas and the cyclic alkylene ketals thereof
US3960569A (en) * 1973-11-20 1976-06-01 Fuji Photo Film Co., Ltd. Diffusion transfer color film unit with hydroxy substituted alkylene amino development accelerators
US4076531A (en) * 1975-07-30 1978-02-28 E. I. Du Pont De Nemours And Company Image anchorage in photographic films
US4030920A (en) * 1976-04-12 1977-06-21 Eastman Kodak Company Processing compositions containing glycols for color transfer processes comprising direct positive silver halide developement
US4264717A (en) * 1978-10-21 1981-04-28 Agfa-Gevaert, A.G. Color photographic material and color photographic processes
EP0266797A2 (en) 1986-11-07 1988-05-11 Fuji Photo Film Co., Ltd. Method of processing silver halide color photographic material and photographic color developing composition
EP0452886A2 (en) 1990-04-17 1991-10-23 Fuji Photo Film Co., Ltd. Method of processing a silver halide color photographic material
EP0720049A2 (en) 1990-05-09 1996-07-03 Fuji Photo Film Co., Ltd. Photographic processing composition and processing method using the same
US5362610A (en) * 1991-10-28 1994-11-08 Konica Corporation Photographic processing agent
US5366853A (en) * 1991-11-06 1994-11-22 Konica Corporation Tablet-shaped processing agent and method for processing silver halide photographic light sensitive materials
US5310633A (en) * 1992-05-13 1994-05-10 Fuji Photo Film Co., Ltd. Bleach-fixing composition for color photographic material and method for processing a color photographic material with the same
US5452045A (en) * 1992-10-30 1995-09-19 Konica Corporation Apparatus for processing a light-sensitive silver halide photographic material
EP0631185A1 (en) 1993-06-11 1994-12-28 Fuji Photo Film Co., Ltd. Method for continuously processing silver halide color photosensitive material
US5409805A (en) * 1993-07-29 1995-04-25 Konica Corporation Solid processing agent for silver halide photographic light-sensitive materials
EP0686875A1 (en) 1994-06-09 1995-12-13 Fuji Photo Film Co., Ltd. Method of processing silver halide color photographic materials
US5576161A (en) * 1994-08-12 1996-11-19 Konica Corporation Silver halide light-sensitive photographic material and method of processing thereof
US5766830A (en) * 1994-09-09 1998-06-16 Konica Corporation Photographic processing method for processing a silver halide photographic light-sensitive material

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