US3362961A - N-substituted hydroxylamines - Google Patents

N-substituted hydroxylamines Download PDF

Info

Publication number
US3362961A
US3362961A US566253A US56625366A US3362961A US 3362961 A US3362961 A US 3362961A US 566253 A US566253 A US 566253A US 56625366 A US56625366 A US 56625366A US 3362961 A US3362961 A US 3362961A
Authority
US
United States
Prior art keywords
silver halide
hydroxylamine
silver
novel
product
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 - Lifetime
Application number
US566253A
Other languages
English (en)
Inventor
Green Milton
Adnan A Sayigh
Ulrich Henri
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.)
Polaroid Corp
Original Assignee
Polaroid Corp
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 GB1053067D priority Critical patent/GB1053067A/en
Priority claimed from US290619A external-priority patent/US3293034A/en
Priority to FR979357A priority patent/FR1399918A/fr
Priority to BE649724D priority patent/BE649724A/xx
Priority to DE19641447719 priority patent/DE1447719A1/de
Application filed by Polaroid Corp filed Critical Polaroid Corp
Priority to US566253A priority patent/US3362961A/en
Application granted granted Critical
Publication of US3362961A publication Critical patent/US3362961A/en
Anticipated expiration legal-status Critical
Expired - Lifetime 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
    • G03C5/3014—Hydrazine; Hydroxylamine; Urea; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
    • C07D211/94—Oxygen atom, e.g. piperidine N-oxide

Definitions

  • a further object of this invention is to provide novel developer compositions useful in diffusion transfer processes.
  • the invention accordingly comprises the several steps and the relation and order of one or more of such steps with respect to each of the others, and the compositions possessing the features, properties and the relation of elements which are exemplified in the following detailed disclosure, and the scope of the application of which will be indicated in the claims.
  • the present invention relates to novel N-substituted hydroxylamines corresponding to the formula:
  • R and R is an alkoxyalkyl or alkoxyalkoxyalkyl radical, and the other of R and R is selected from the group consisting of alkyl, alkoxyalkyl, alkoxyalkoxylalkyl, or alkenyl radical.
  • the alkyl, alkoxy and alkenyl radicals preferably contain from 1 to 3 carbons, but may contain more carbons provided the resulting compound is soluble in 5% aqueous sodium hydroxide.
  • the preferred alkoxyalkyl hydroxylamines include:
  • an exposed silver halide emulsion is treated with a liquid processing composition while in superposed relationship with an image-receiving material.
  • the liquid processing composition develops exposed silver halide to silver and reacts with unexposed silver halide to form a complex silver salt which is transferred to the image-receiving material and there reduced to silver to form a positive print.
  • the processing composition includes a silver halide solvent, such as sodium thiosulfate, and may also contain a film-forming material for increasing the viscosity of the composition.
  • silver halide solvent refers to reagents which will form a soluble complex with silver halide, as is Well known in the art of forming silver images by transfer.
  • EXAMPLE 6 A silver iodobromide emulsion sold by E. I. du Pont de Nemours & C0,, Wilmington, Del., was exposed and processed with a composition comprising:
  • the image-receiving element comprised a silver-receptive stratum containing silver precipitating nuclei dispersed n a matrix of colloidal silica coated on a water-impervious base according to the practice described in US. Patent No. 2,823,122, issued Feb. 11, 1958.
  • the exposed emulsion and the image-receiving element were advanced, in superposed relationship, between a pair of pressure-applying rollers to spread the processing solution between them in a thin layer. After an imbibition period of approximately sixty seconds, the emulsion, together with the layer of solution, was stripped from the image-receiving element to uncover the positive print.
  • EXAMPLE 7 The procedure described in Example 6 was repeated using approximately 75 cc. of N,N-di-(2-methoxyethyl)- hydroxylamine as the developing agent.
  • EXAMPLE 8 The procedure described in Example 6' was repeated using a mixture of approximately 40* cc. of N,N-di-(2- ethoxyethyl)-hydroxylamine and approximately 6 cc. of N,N-di-(2-methoxymethyl)-hydroxylamine.
  • the silver transfer images obtained in the above examples were characterized by substantially longer range and more neutral tones than were obtained using N,N- diethyl-hydroxylamine under similar conditions.
  • the latter compound is characterized by substantial volatility at room temperatures. While this a desirable property for many purposes, there results a strong fishy or amine odor which is objectionable in many applications, e.g., where a number of prints are to be made in a short time in the same room.
  • the novel developing agents of this invention do not exhibit strong odors at room temperature because their vapor pressures are appreciably lower than that of N,N-diethyl-hydroxylamine.
  • the novel developing agents of this invention also are characterized by having colorless or substantially colorless oxidation products.
  • the induction periods of the novel developing agents of this invention were tested by applying an approximately 1 molar solution of the hydroxylamine in 5% sodium hydroxide to a fogged silver iodobromide emulsion and noting the elapsed time before strong developing starts.
  • the compounds prepared in Examples 15 all showed induction periods of from 1 to 2 seconds as compared with 2.5 to 3 seconds for N,N-diethylhydroxylamine and 8 seconds for N,N-dimethyl-hydroxylamine.
  • the developed area also reached its blackest color (or full development) in less or no longer times than the last-mentioned compounds.
  • R and R taken together may comprise the atoms necessary to complete a heterocyclic ring including the nitrogen atom, a carbon atom of said heterocyclic ring being substituted by an alkoxy group.
  • An example of such a compound is N-hydroxyi ethoxypiperidine, the synthesis of which is set forth in the following example.
  • This compound gave good results when used as a silver halide developing agent in the manner described above, giving a development induction period of 4 seconds, slightly longer than that of N,N-diethylhydroxy1amine.
  • novel developing agents may be employed in solution or they may be initially incorporated in a layer of the photosensitive or image-receiving elements; in the latter case they are preferably employed as acid salts, e.g., as the hydrochloride or hydrobromide.
  • N,N-di- (Z-methoxyethoxyethyl -hydroxylamine N-ethyl-N-2ethoxyethyl-hydroxylamine.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Hydrogenated Pyridines (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US566253A 1963-06-26 1966-07-19 N-substituted hydroxylamines Expired - Lifetime US3362961A (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
GB1053067D GB1053067A (en, 2012) 1963-06-26
FR979357A FR1399918A (fr) 1963-06-26 1964-06-23 Nouveaux agents de développement de l'halogénure d'argent
BE649724D BE649724A (en, 2012) 1963-06-26 1964-06-25
DE19641447719 DE1447719A1 (de) 1963-06-26 1964-06-26 Photographischer Entwickler
US566253A US3362961A (en) 1963-06-26 1966-07-19 N-substituted hydroxylamines

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US290619A US3293034A (en) 1963-06-26 1963-06-26 Alkoxy hydroxylamines as photographic developers
US566253A US3362961A (en) 1963-06-26 1966-07-19 N-substituted hydroxylamines

Publications (1)

Publication Number Publication Date
US3362961A true US3362961A (en) 1968-01-09

Family

ID=26966299

Family Applications (1)

Application Number Title Priority Date Filing Date
US566253A Expired - Lifetime US3362961A (en) 1963-06-26 1966-07-19 N-substituted hydroxylamines

Country Status (4)

Country Link
US (1) US3362961A (en, 2012)
BE (1) BE649724A (en, 2012)
DE (1) DE1447719A1 (en, 2012)
GB (1) GB1053067A (en, 2012)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
US4801516A (en) * 1986-06-25 1989-01-31 Fuji Photo Film Co., Ltd. Method of processing silver halide color photographic material using a developer comprising a hydroxylamine and an antifoggant
EP0565315A3 (en) * 1992-04-08 1994-08-17 Chugai Shashin Yakuhin Colour development composition and method of processing silver halide colour photographic material using the same
US5646327A (en) * 1995-12-08 1997-07-08 Eastman Kodak Company Method for preparing hydroxylamines using vinylic compounds without base neutralization and reaction mixture produced thereby
WO2004062780A3 (en) * 2003-01-09 2004-09-02 Argonaut Technologies Inc Stirring system

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0255292B1 (en) * 1986-07-26 1994-05-11 Konica Corporation Processing solution of light-sensitive silver halide color photographic material and processing method of the same

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2185163A (en) * 1935-07-24 1939-12-26 Ig Farbenindustrie Ag Polyoxyalkylene ammonium compounds and process of preparing them
US2843481A (en) * 1954-07-19 1958-07-15 Polaroid Corp Photographic processes
US2857274A (en) * 1953-09-04 1958-10-21 Polaroid Corp Photographic compositions and processes
US2857276A (en) * 1954-11-23 1958-10-21 Polaroid Corp Photographic processes and compositions useful therein

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2185163A (en) * 1935-07-24 1939-12-26 Ig Farbenindustrie Ag Polyoxyalkylene ammonium compounds and process of preparing them
US2857274A (en) * 1953-09-04 1958-10-21 Polaroid Corp Photographic compositions and processes
US2843481A (en) * 1954-07-19 1958-07-15 Polaroid Corp Photographic processes
US2857276A (en) * 1954-11-23 1958-10-21 Polaroid Corp Photographic processes and compositions useful therein

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4801516A (en) * 1986-06-25 1989-01-31 Fuji Photo Film Co., Ltd. Method of processing silver halide color photographic material using a developer comprising a hydroxylamine and an antifoggant
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
EP0565315A3 (en) * 1992-04-08 1994-08-17 Chugai Shashin Yakuhin Colour development composition and method of processing silver halide colour photographic material using the same
US5646327A (en) * 1995-12-08 1997-07-08 Eastman Kodak Company Method for preparing hydroxylamines using vinylic compounds without base neutralization and reaction mixture produced thereby
WO2004062780A3 (en) * 2003-01-09 2004-09-02 Argonaut Technologies Inc Stirring system

Also Published As

Publication number Publication date
GB1053067A (en, 2012)
BE649724A (en, 2012) 1964-12-28
DE1447719A1 (de) 1969-01-23

Similar Documents

Publication Publication Date Title
US3293034A (en) Alkoxy hydroxylamines as photographic developers
US3287125A (en) Aminoalkyl hydroxylamines as photographic developers
US3455916A (en) Certain n,n-disubstituted hydroxylamines
JPH0473573B2 (en, 2012)
US3301678A (en) Process for stabilizing photographic images with heat
US3362961A (en) N-substituted hydroxylamines
DE1931057C2 (de) Verfahren zur Herstellung farbphotographischer Bilder
US3491151A (en) Preparation of alkylated hydroxylamines
US3938995A (en) Silver halide color photographic element and process containing leuco dyes
US3549370A (en) Quaternary ammonium bisulfites,sulfites or pyrosulfites as developer preservatives
US2949359A (en) Process for developing silver halide emulsions
US2857275A (en) Photographic compositions and processes
US2552241A (en) p-phenylenediamines containing alkylacylamidoethyl or alkylacylamidoethoxy ring substituents
US3772021A (en) Process for the development of silver halide light-sensitive material
US3002997A (en) Photographic products, processes and compositions
US3806345A (en) Hydroxylamine photographic developer
US3578449A (en) Transfer image process utilizing an organic phosphine as silver halide solvent
US3311474A (en) Photographic material
US3619185A (en) Photographic processing compositions and processes using same
US3337344A (en) Color photographic silver halide emulsion
US2843481A (en) Photographic processes
US4511733A (en) Fluorine-containing aminocarboxylic acid compounds
US3331850A (en) 5-(aryloxymethyl)-2-oxazolidinethiones
US3975423A (en) Alkylthioalkyl-substituted alkylsulfonylacetonitriles
GB851816A (en) Light-sensitive silver halide emulsions