US3880660A - Processing silver halide photographic material with a polymeric defoaming agent - Google Patents

Processing silver halide photographic material with a polymeric defoaming agent Download PDF

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Publication number
US3880660A
US3880660A US312792A US31279272A US3880660A US 3880660 A US3880660 A US 3880660A US 312792 A US312792 A US 312792A US 31279272 A US31279272 A US 31279272A US 3880660 A US3880660 A US 3880660A
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US
United States
Prior art keywords
processing
photographic material
solution
polymer
silver halide
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Expired - Lifetime
Application number
US312792A
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English (en)
Inventor
Masao Ishihara
Sadatugu Terada
Masayoshi Mayama
Tohru Kobayashi
Riyouzou Maeda
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Konica Minolta Inc
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Konica Minolta Inc
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Assigned to KONICA CORPORATION reassignment KONICA CORPORATION RELEASED BY SECURED PARTY (SEE DOCUMENT FOR DETAILS). Assignors: KONISAIROKU PHOTO INDUSTRY CO., LTD.
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
    • C07D213/20—Quaternary compounds thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/10—Esters
    • C08F20/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
    • 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
    • G03C5/29—Development processes or agents therefor
    • G03C5/305—Additives other than developers
    • G03C5/3056—Macromolecular additives

Definitions

  • R is a hydrogen atom or a methyl group
  • X is an anion
  • Q* is
  • R is a lower alkyl, phenyl or benzyl group
  • R and R are individually a lower alkyl group; provided that when R is a lower alkyl group, R and R may form together a nitrogen-containing 5-to-6membered heterocyclic nucleus
  • A is a group of nonmetal atoms selected from carbon, nitrogen and sulfur. which are necessary to form a 5-to-6-membered heterocyclic nucleus together with N' C-.
  • homopolymers or copolymers containing as polymer components such unit components of the general formula shown below are excellent defoaming agents having the above-mentioned characteristics, and have accomplished, based on the above finding, a process for treating silver halide light-sensitive photographic materials without causing any drawbacks derived from the foaming of processing solutions, characterized in that the said defoaming agents are incorporated into photographic processing solutions and/or silver halide light-sensitive photographic materials to be treated.
  • R is a lower alkyl, phenyl or benzyl group
  • R and R are individually a lower alkyl group, provided that in case R is a lower alkyl group, R and R may form together a nitrogen-containing 5 to o-membered hetcrocyclic nucleus
  • the polymerization degree of such homopolymer or copolymer is found to be within the range of from 20 to 1500.
  • Typical examples of the homopolymers and copolym'ers which contain as polymer components the unit components having the aforesaid general formula, are enumerated below by way of structural formulas. in which 11,11 and n: are individually an average polymerization degree. and n n is a polymerization molar rano.
  • the defoaming agents used in HESIS EXAMPLE 2 the present invention include not only homopolymers S h i f the exemplified compound (9) but also copolymers with other monomers such as. for A example. acrylamide. N-vinylpyrrolidone. N.N- hlimxture comprlsmg (1 m l of y y dimethylacrylamide. diacetonacrylamide. acrylic acid. "T dcrylne 1 molt?) of Pl' hydrochlomethacrylic acid. methyl acrylate.
  • a mixture comprising 142 g. (1 mole) of glycidyl 40 methacrylate. 96 g. 1 mole) of trimethylamine hydrochloride. 240 g. of benzyl alcohol and 0.1 g. of hydroquinone was reacted with stirring at 60C. for 70 minutes. Thereafter. the reaction mixture was poured into acetone to deposit crystals. The crystals were recovered by filtration and then recrystallized from ethanol to obtain 150 g. of a monomer of the formula.
  • the above-mentioned homopolymers and copolymers used in the present invention have molecular weights in the range from 5.000 to 200.000. preferably from 10.000 to 50.000. 1n the ease of copolymers.
  • the copolymerization ratio is preferably such that the amount of the unit component of the aforesaid general formula is 30 mole percent or more.
  • the amount of these compounds to be incorporated into processing solutions are preferably in proportion to the amounts of foaming substances accumulated in the processing solutions, as is clear from the application purposes of said compounds.
  • the compounds are desired to be incorporated into one of the layers constituting silver halide light-sensitive photographic materials, it is most effective to incorporate the compounds into the outer-most layers, e.g. the protective layer or the outer-most layer on the reverse side, which contact directly with the processing solutions.
  • the layers, into which the compounds have been incorporated. may further be coated externally with other layers, so far as the dissolving-out of the compounds is not disturbed.
  • Photographic materials include various silver halide lightsensitive materials to be processed according to diffusion transfer method, direct positive method, silver dye bleaching method and stabilization method, in addition to black-white and color negative films, reversal positive films and printing papers which are processed according to ordinary methods.
  • the compounds used in the present invention are incorporated into photographic materials in such a manner that the compound is dissolved in water or an organic solvent or a mixture thereof, and the resulting solution is added to a coating liquid for preparation of a photographic material, thereby incorporating the compound into one of the layers of the photographic material, or the abovementioned solution is directly coated, if necessary after incorporation of a coating aid, on the surface of a photographic material.
  • the amount of the compound to be incorporated into the said layer of photographic material is to 50 percent by weight based on the weight of gelatin, while the proportion of the compound to be directly coated on the photographic material is 2 mg/m or more, whereby favorable effects can be attained.
  • Processing solutions include various processing solutions such as prehardening solution, developing solution, stopping solution, hardening solution, bleaching solution, and such composite solutions as monobath developing solution and bleach-fix solution.
  • processing solutions such as prehardening solution, developing solution, stopping solution, hardening solution, bleaching solution, and such composite solutions as monobath developing solution and bleach-fix solution.
  • the compounds may be directly added to the processing solutions or may be incorporated into processing agents to be dissolved.
  • Typical processings include any development treatments such as cinefilm development, tank development and spray type development.
  • procedures for agitation of the processing solutions include all such procedures as circulation of the solutions, stirring by means of a stirrer. introduction of nitrogen or air bubbles, jetting of the solutions, vibration or rotation of light-sensitive photographic materials.
  • sample (I) (II) (III) water 800 ml 800 ml 800 ml. Benzyl alcohol 3.8 ml. 3.8 ml. 3.8 ml. Sodium hexamcthaphosphatc 2.0 g. 2.0 g. 2.0 g.
  • sulfonate 17 aqueous solution
  • Compound as defoaming Excmplified Control agent W1 aqueous compound compound solution) (I) 0.5 mlv 0.5 ml. Water to make I liter 1 liter 1 liter Table 1 Time after foaming Average height of b shaking foams (I) (II) (III) 10sec. l8 mm. 0 mm. 9 mm. 30 see. 13 mm. 7 mm. so see. 12 mm. 6 mm.
  • the sample (ll), which has been incorporated with the exemplified compound 1 is less in foaming degree. and the foams formed in the sample (ll) disappear quickly. Although certain deforming effect is observed in the sample (III), which has been incorporated with the control compound, the effect is lower than that observed in the sample (ll).
  • a sample (I') identical in composition with the sample (I) except that the amount of the surface active agent was made 1.5 ml.. and a sample (ll) identical in composition with the sample (ll) except that the amount of the surface active agent was made 1.5 ml. and the amount of the exemplified compound (1 was made 0.5 ml.. were individually subjected to the same measurement as above.
  • the results obtained were as set forth in Table 27 Table 2 Time after foaming Average height by shaking of foam (l') (ll') I see. 35 mm. 3 mm. see. mm. 2 mm. on see. 31 mm. 0 mm. lZU sec. 30 mm. 0 mm.
  • EXAMPLE 1 Using an automatic developing machine of such a type as to agitate the developer by introduction of nitrogen gas, two silver halide light-sensitive color photographic films were individually treated with each of the developer (1) used in the test example and a developer (Il") identical in composition with the developer (ll) used in the test example except that 0.5 ml. of a 1 percent aqueous solution of the exemplified compound (3) was used in place of the exemplified compound l In this case. the developers (I) and (II) were individually measured in degree of foaming due to agitation derived from introduction of gas.
  • the method adopted in this case was such that the developer was charged into the same test tube as in the test example, nitrogen gas was continuously introduced into the developer for 30 seconds, and then the averge height of foams formed in the developer was measured after 10. 30 and 60 seconds.
  • the results obtained were as set forth in Table 3.
  • EXAMPLE 2 in this example were used two automatic developing machines for silver halide black-white printing papers.
  • a developer of the prescription (lll) shown below was charged into the developer tank of one developing machine. and a stop-fixer of the prescription (1V) shown below was charged into the stop-fixer tank of the same machine.
  • the same developer (III) as above was charged into the developer tank of the other developing machine.
  • a stopfixer of the prescription (V) shown below was charged into the stopfixer tank of the same machine.
  • EXAMPLE 3 In this example were used two automatic developing machines (A) and (B) for silver halide black-white printing papers.
  • the developer (III) used in Example 2 was charged into the developer tank of each developing machine, and the stop-fixer used in Example 2 was charged into the stop-fixer tank thereof.
  • Using these developing machines a large number of printing papers were processed. That is, the printing papers used in Example 2 were treated with the machine (A), and the same printing papers as above, except that 5 ml/m of a 2 percent aqueous solution of the exemplified compound (5) had been, coated by spraying on the surface of the emulsion layer of each printing paper, followed by drying, were treated with the machine (B).
  • EXAMPLE 4 In this example were used two automatic developing machines (A) and (B) of such a type as shown in Exam- 5 ple l.
  • the developer (I) used in the test example was charged into the developer tank of each developing machine.
  • the developing machine (A) was used to treat the silver halide light-sensitive color photographic film used in Example 1, and the developing machine 10 (B) was used to process the same photographic film as above except that ml/m of a O.l percent methanolacetone (:70) solution of the exemplified compound (6) had been coated on the reverse side of the film, followed by hot air drying.
  • the developer used in each developing machine was measured in degree of foaming clue to agitation derived from introduction of gas.
  • the method adopted in this case was such that nitrogen gas was continuously introduced into the developer for 30 seconds, and then the average height of foams formed in the developer was measured after 10, 30 and 60 seconds, like in Example I.
  • the results obtained were as set forth in Table 6.
  • R is hydrogen or Xeis an anion
  • Q is -N-- R2 01 -N -s 2.
  • acrylamide N-vinylpyrrolidone. N.N- dimethylacrylamide. diacetonacrylamide. acrylic acid.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • General Physics & Mathematics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
US312792A 1971-12-07 1972-12-07 Processing silver halide photographic material with a polymeric defoaming agent Expired - Lifetime US3880660A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP46098316A JPS5033849B2 (enrdf_load_stackoverflow) 1971-12-07 1971-12-07

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US3880660A true US3880660A (en) 1975-04-29

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US (1) US3880660A (enrdf_load_stackoverflow)
JP (1) JPS5033849B2 (enrdf_load_stackoverflow)
DE (1) DE2259871A1 (enrdf_load_stackoverflow)
GB (1) GB1408464A (enrdf_load_stackoverflow)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4135931A (en) * 1976-08-27 1979-01-23 Fuji Photo Film Co., Ltd. Method of image formation
US4138257A (en) * 1976-05-04 1979-02-06 Konishiroku Photo Industry Co., Ltd. Process for the treatment of photographic materials
US4209583A (en) * 1977-05-05 1980-06-24 Agfa-Gevaert, A.G. Corrosion preventative for two-bath stabilizer baths
US4780398A (en) * 1986-08-28 1988-10-25 Olin Hunt Specialty Products, Inc. Bleaching composition and process for color photographic materials

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5065050U (enrdf_load_stackoverflow) * 1973-10-16 1975-06-12
JPS5789976A (en) * 1980-11-26 1982-06-04 Matsushita Electric Ind Co Ltd Method and device for ink recording

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2375007A (en) * 1943-04-15 1945-05-01 Shell Dev Antifoaming composition
US3251782A (en) * 1963-06-28 1966-05-17 Du Pont Process for inhibiting foam formation in aqueous talc dispersions

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2375007A (en) * 1943-04-15 1945-05-01 Shell Dev Antifoaming composition
US3251782A (en) * 1963-06-28 1966-05-17 Du Pont Process for inhibiting foam formation in aqueous talc dispersions

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4138257A (en) * 1976-05-04 1979-02-06 Konishiroku Photo Industry Co., Ltd. Process for the treatment of photographic materials
US4135931A (en) * 1976-08-27 1979-01-23 Fuji Photo Film Co., Ltd. Method of image formation
US4209583A (en) * 1977-05-05 1980-06-24 Agfa-Gevaert, A.G. Corrosion preventative for two-bath stabilizer baths
US4780398A (en) * 1986-08-28 1988-10-25 Olin Hunt Specialty Products, Inc. Bleaching composition and process for color photographic materials

Also Published As

Publication number Publication date
GB1408464A (en) 1975-10-01
DE2259871A1 (de) 1973-06-14
JPS4863725A (enrdf_load_stackoverflow) 1973-09-04
JPS5033849B2 (enrdf_load_stackoverflow) 1975-11-04

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Owner name: KONICA CORPORATION, JAPAN

Free format text: RELEASED BY SECURED PARTY;ASSIGNOR:KONISAIROKU PHOTO INDUSTRY CO., LTD.;REEL/FRAME:005159/0302

Effective date: 19871021