GB1045242A - Diazonium compounds and diazotype material - Google Patents

Diazonium compounds and diazotype material

Info

Publication number
GB1045242A
GB1045242A GB2596/64A GB259664A GB1045242A GB 1045242 A GB1045242 A GB 1045242A GB 2596/64 A GB2596/64 A GB 2596/64A GB 259664 A GB259664 A GB 259664A GB 1045242 A GB1045242 A GB 1045242A
Authority
GB
United Kingdom
Prior art keywords
group
cycloalkyl
radical
alkyl
substituted
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
GB2596/64A
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.)
Grinten Chem L V D
Chemische Fabriek L Van der Grinten NV
Original Assignee
Grinten Chem L V D
Chemische Fabriek L Van der Grinten NV
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 Grinten Chem L V D, Chemische Fabriek L Van der Grinten NV filed Critical Grinten Chem L V D
Publication of GB1045242A publication Critical patent/GB1045242A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/40—Radicals substituted by oxygen atoms
    • C07D307/42—Singly bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C275/40—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by nitrogen atoms not being part of nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • 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
    • G03C1/00—Photosensitive materials
    • G03C1/52—Compositions containing diazo compounds as photosensitive substances
    • G03C1/54—Diazonium salts or diazo anhydrides

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heat Sensitive Colour Forming Recording (AREA)

Abstract

The invention comprises a diazonium compound of the general formula <FORM:1045242/C2/1> in which X is an anion, R1 is an alkyl, branched alkyl, cycloalkyl or aralkyl radical, R2 represents hydrogen or an alkyl, branched alkyl, cycloalkyl, aralkyl, aryl or heterocyclic radical, or an alkoxy, branched alkoxy, cycloalkyloxy, aralkyloxy, aryloxy or a hetercyclic radical, which is attached to the CO-group via an oxygen atom, or represents a substituted amino group or a substituted amidocarbonyl or a substituted amidocarbonylalkyl group, R3 is an alkylsulphonamido, aralkylsulphonamido, arylsulphonamido, 2 - amino - 4 - imino - 1,3,5-triazinyl (1)-group or a -NH-CO-R5-group in which R5 represents hydrogen or an alkyl, branched alkyl, cycloalkyl, aralkyl, aryl or heterocyclic radical, or an alkoxy, branched alkoxy, cycloalkoxy, aralkoxy, aryloxy radical or a heterocyclic radical which is attached to the CO-group via an oxygen atom, or represents a substituted amino radical or a substituted amidocarbonyl group, or a substituted amidocarbonylalkyl group, and R4 is an alkyl, branched alkyl, cycloalkyl, aralkyl or aryl radical. The novel diazonium compounds may be made from a 4-chloro-2-aminophenolalkyl, branched alkyl, cycloalkyl, aralkyl or aryl ether whereby the amino group is (a) acylated with, e.g., a carbohalide or an ester of chloroformic acid, or (b) converted into a sulphonamido group using an organic sulphochloride, or (c) reacted with dicyandiamide to form a bi-guanidino group, whereupon ring closure to form a triazinyl ring with an organic carboxylic acid or its anhydride takes place. The ether or 4-chloro-2-(acylamino, sulphonamido or triazinyl) phenol so formed is nitrated and its chlorine atom is then replaced by a monoalkyl, branched alkyl, cycloalkyl, or aralkylamino group, which is subsequently acylated. The nitro group in the product is reduced to the corresponding amine and the diazonium compound is made in the usual way. The 4-chloro-2-amino-phenol ethers can be made by introducing a nitro group in the ortho position of 4-chlorophenol, etherifying the hydroxyl group and reducing the nitro group to an amino group. The aryl ethers are obtained by fusing 2,5-dichloronitrobenzene with a hydroxyaryl compound and potassium hydroxide and reducing the nitro group.
GB2596/64A 1963-02-01 1964-01-21 Diazonium compounds and diazotype material Expired GB1045242A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
NL288469 1963-02-01

Publications (1)

Publication Number Publication Date
GB1045242A true GB1045242A (en) 1966-10-12

Family

ID=19754387

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2596/64A Expired GB1045242A (en) 1963-02-01 1964-01-21 Diazonium compounds and diazotype material

Country Status (10)

Country Link
US (1) US3338713A (en)
BE (1) BE643153A (en)
CH (1) CH461267A (en)
DE (1) DE1251656B (en)
DK (1) DK114878B (en)
ES (1) ES295910A1 (en)
FI (1) FI40438B (en)
GB (1) GB1045242A (en)
NL (2) NL288469A (en)
SE (1) SE315496B (en)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL133921C (en) * 1964-06-01 1972-04-17
DD54880A (en) * 1965-07-01
NL132069C (en) * 1965-07-02
US3463639A (en) * 1965-12-15 1969-08-26 Addressograph Multigraph Benzene diazonium salts useful in diazotype materials having ortho carboxamido substitution
US3547637A (en) * 1966-07-06 1970-12-15 Keuffel & Esser Co Light-sensitive diazotype material
US3868255A (en) * 1969-07-23 1975-02-25 Gaf Corp Diazonium salts and diazotype materials
US4043816A (en) * 1972-05-26 1977-08-23 Oce-Van Der Grinten N.V. Photographic process for making diazotype copies utilizing small quantity of liquid developer
NL172373C (en) * 1972-05-26 1983-08-16 Oce Van Der Grinten Nv METHOD FOR MAKING DIAZOTYP COPIES
US4306007A (en) * 1978-03-13 1981-12-15 Am International, Inc. Process of making and using fade-resistant diazo microfilm
CH626877A5 (en) * 1978-08-22 1981-12-15 Aerni Leuch Ag

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB521492A (en) * 1938-09-20 1940-05-23 S C & P Harding Ltd Improvements in the production of diazotype light-sensitive layers
US2326782A (en) * 1941-04-16 1943-08-17 Keuffel & Esser Co Photosensitive material
FR1001352A (en) * 1946-04-24 1952-02-22 Francolor Sa Dyes for color photography
US2665985A (en) * 1949-10-26 1954-01-12 Keuffel & Esser Co Light-sensitive diazo compounds and photoprint material prepared therefrom
NL218185A (en) * 1957-06-17

Also Published As

Publication number Publication date
US3338713A (en) 1967-08-29
CH461267A (en) 1968-08-15
SE315496B (en) 1969-09-29
BE643153A (en) 1964-07-30
DK114878B (en) 1969-08-11
ES295910A1 (en) 1964-03-16
FI40438B (en) 1968-09-30
NL288469A (en)
DE1251656B (en) 1967-10-05
NL121032C (en)

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