GB757271A - Improvements in photographic developing agents - Google Patents

Improvements in photographic developing agents

Info

Publication number
GB757271A
GB757271A GB22511/54A GB2251154A GB757271A GB 757271 A GB757271 A GB 757271A GB 22511/54 A GB22511/54 A GB 22511/54A GB 2251154 A GB2251154 A GB 2251154A GB 757271 A GB757271 A GB 757271A
Authority
GB
United Kingdom
Prior art keywords
pyrazolidone
methyl
cr1r2
dimethyl
ethyl
Prior art date
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
Application number
GB22511/54A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Kodak Ltd
Original Assignee
Kodak Ltd
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
Application filed by Kodak Ltd filed Critical Kodak Ltd
Publication of GB757271A publication Critical patent/GB757271A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • G03C5/30—Developers
    • G03C5/3028—Heterocyclic compounds
    • G03C5/3035—Heterocyclic compounds containing a diazole ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/06—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D231/08—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with oxygen or sulfur atoms directly attached to ring carbon atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)

Abstract

The invention comprises pyrazolidones of the formula <FORM:0757271/IV(a)/1> where R is alkyl, hydroxyalkyl, carboxyalkyl, or aryl and R1 and R2 are alkyl (same or different), and their preparation from R.NH.NH2 and Hal-CH2-CR1R2-CO-Hal with an acid-binding agent mixed at 0-10 DEG C. and then heated, e.g. to 100 DEG C. for 1-10 hours. Substituents in the aryl group R may then be modified, e.g. acyloxyalkyl, acyloxy and acylamino hydrolysed to hydroxyalkyl, hydroxy or amino respectively, or nitro reduced to amino. Examples are given of the preparation of 1-phenyl-4 : 4-dimethyl-3-pyrazolidone, 1 - p - tolyl - 4 : 4 - dimethyl - 3-pyrazolidone and 1 - (p - b - acetoxyethylphenyl) - 4 : 4 - dimethyl - 3 - pyrazolidone, hydrolysed to the b -hydroxyethyl compound. The products are photographic developing agents, in which process they are oxidized to bimolecular compounds, probably bis-[1-(alkyl or aryl) - 4 : 4 - dialkyl - 3 - pyrazolidon - 5-yls]. The product from 1-phenyl-4 : 4-di-methyl-3-pyrazolidone is isolated. Other specified products of the invention are 1-(p-aminophenyl) - 4 - methyl - 4 - propyl - 3 - pyrazolidone, 1 - (p - chlorophenyl) - 4 - methyl - 4-ethyl - 3 - pyrazolidone, 1 - (p - acetamidophenyl) - 4 : 4 - diethyl - 3 - pyrazolidone, 1-(p - methoxyphenyl) - 4 : 4 - diethyl - 3 - pyrazolidone, 1 - (7 - hydroxy - 2 - naphthyl) - 4-methyl - 4 - propyl - 3 - pyrazolidone, 1 - (mchlorophenyl) - 4 - methyl - 4 - ethyl - 3 - pyrazolidone, 1 - (m - acetamidophenyl) - 4 : 4-dimethyl - 3 - pyrazolidones: 1 - (p - nitrophenyl), 1 - (p - cyanophenyl), 1 - (p - acetamidophenyl), 1 - (p - benzylphenyl), 1 - (pcarboxyphenyl), 1 - (m - aminophenyl), 1-methyl, 1-carboxymethyl and 1-hydroxyethyl. Other groups specified for R are ethyl, propyl, isobutyl, carboxyethyl, o- and m-tolyl, o- and m - methoxyphenyl, p - dialkylaminophenyl, o- and m-nitrophenyl, bromophenyl, o-chlorophenyl, o- and m-carboxyphenyl, hydroxyalkylphenyl, hydroxyphenyl and a - and b -naphthyl. b -Halofatty acid halides of the above formula are made from aldehydes CHR1R2-CHO by treatment with alkaline formaldehyde to give HO-CH2-CR1R2-CHO, oxidation to the acid HO-CH2-CR1R2-COOH and treatment of the latter with thionyl chloride. Compounds in which R1 and R2 are identical can also be made from CH2-CR1R2-COOH and sulphuryl chloride. The preparation of b -chlorotrimethylacetyl chloride is exemplified. Other products are mentioned. p - (b - Acetoxyethyl) - phenylhydrazine hydrochloride is made by diazotizing p-(b -acetoxy-ethyl)-aniline and reducing the product with stannous chloride.
GB22511/54A 1953-08-03 1954-08-03 Improvements in photographic developing agents Expired GB757271A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US372148A US2772282A (en) 1953-08-03 1953-08-03 3-pyrazolidones

Publications (1)

Publication Number Publication Date
GB757271A true GB757271A (en) 1956-09-19

Family

ID=23466906

Family Applications (1)

Application Number Title Priority Date Filing Date
GB22511/54A Expired GB757271A (en) 1953-08-03 1954-08-03 Improvements in photographic developing agents

Country Status (4)

Country Link
US (1) US2772282A (en)
BE (1) BE530884A (en)
FR (1) FR1131853A (en)
GB (1) GB757271A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6083673A (en) * 1996-01-23 2000-07-04 Eastman Kodak Company Organic/inorganic developer composition

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3166568A (en) * 1965-01-19 Therapeutic compositions containing
NL279140A (en) * 1961-05-31
NL125600C (en) * 1962-06-07
US3453109A (en) * 1966-06-24 1969-07-01 Eastman Kodak Co Forming a relief by developing and hardening an exposed unhardened silver halide emulsion in the exposed areas with 3-pyrazolidones having hydroxymethyl substitution in the 4-position
US4209580A (en) * 1978-10-02 1980-06-24 Eastman Kodak Company Substituted 1-phenyl-3-pyrazolidinone electron transfer agents
US4266002A (en) * 1978-10-02 1981-05-05 Eastman Kodak Company Substituted 1-phenyl-3-pyrazolidinone electron transfer agents
JPS5850534A (en) * 1981-09-21 1983-03-25 Fuji Photo Film Co Ltd Multilayer color photosensitive material
JPH0648371B2 (en) * 1986-11-07 1994-06-22 富士写真フイルム株式会社 Processing method of silver halide photographic light-sensitive material for X-ray
CA2026606A1 (en) * 1989-11-13 1991-05-14 Eastman Kodak Company Photographic developing solution for use with fore-hardened x-ray films
DE69223192T2 (en) * 1991-08-16 1998-06-18 Agfa Gevaert Nv A silver halide photographic material
GB9623709D0 (en) * 1996-11-14 1997-01-08 Kodak Ltd Novel auxiliary developing agents,photographic materials incorporating them and the use thereof
US6087084A (en) * 1997-11-14 2000-07-11 Eastman Kodak Company Auxiliary developing agents, photographic materials incorporating them and the use thereof

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB542502A (en) * 1940-07-10 1942-01-13 John David Kendall Improvements in or relating to photographic development processes
US2688024A (en) * 1951-10-17 1954-08-31 Ilford Ltd Production of 3-pyrazolidones
US2704762A (en) * 1952-08-25 1955-03-22 Ilford Ltd Production of 3-pyrazolidones

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6083673A (en) * 1996-01-23 2000-07-04 Eastman Kodak Company Organic/inorganic developer composition

Also Published As

Publication number Publication date
BE530884A (en)
US2772282A (en) 1956-11-27
FR1131853A (en) 1957-02-28

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