US2605182A - Diazotypes containing n-substituted p-diazoanilines having radicals of at least four conjugated c-c double bonds as n-substituents - Google Patents

Diazotypes containing n-substituted p-diazoanilines having radicals of at least four conjugated c-c double bonds as n-substituents Download PDF

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Publication number
US2605182A
US2605182A US788656A US78865647A US2605182A US 2605182 A US2605182 A US 2605182A US 788656 A US788656 A US 788656A US 78865647 A US78865647 A US 78865647A US 2605182 A US2605182 A US 2605182A
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United States
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parts
diazotype
light
diazo
mixture
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Expired - Lifetime
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US788656A
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English (en)
Inventor
Willard D Peterson
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GAF Chemicals Corp
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General Aniline and Film Corp
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Priority to BE486034D priority Critical patent/BE486034A/xx
Application filed by General Aniline and Film Corp filed Critical General Aniline and Film Corp
Priority to US788656A priority patent/US2605182A/en
Priority to FR988975D priority patent/FR988975A/fr
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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
    • G03C1/00—Photosensitive materials
    • G03C1/52—Compositions containing diazo compounds as photosensitive substances
    • G03C1/54—Diazonium salts or diazo anhydrides

Definitions

  • This invention relates to .diazotype reproducing material which will reproduce positive copies from positive originals, and more particularly to the use of diazo compounds in said diazotype materials as the light sensitive element which will decompose under exposure to long wave length light.
  • diazo compounds In the reproduction of positive copies from positive originals bythe diazotype method diazo compounds have been employed which will be decomposed most effectively. by light in the range of 3600 A. to 4200 A.
  • the diazocompounds which have thus beenemployed hayenotbeen selected because of this'sensitivity to that range of light emanations, but have"beenselectedbecause they possess other properties which particularly suit them for use in the diazotype process; Thus these diazos will couple with azo dye coupling 4 Claims. (Cl. 957) exposure; equipment to sources-.01"; 'slight zuzliieh components in the proper coupling medium or atmosphere to produce .d-yeimages in a wide range 'of colors, particularly in deep shades.
  • Diazo derivatives of o-amino naphthols have also been employed to some extent and monodiazo derivatives of ophenyldiamines where the undiazotized amino group is at least mono-substitutedby one of the above-mentioned substituent groups have been suggested, but are of little importance commercially.
  • These diazo compounds which have been found mostsuitable for diazotype reproduction work as indicated above are most effectively decomposed by sources of light emitting rays in the 3600A. to 4200 A. line. In general, it can be said that diazotype materials hereto fore employed are decomposed only by Wave length of light shorter than 4800-5000 A.
  • incandescent lamp's emit light which is particularly'rich in wave lengths above thei4000 line they constitute a -wasteiul source of energy for this purpose.
  • the new class of diazo compounds may be defined as'N-substituted p-diazoanilines inwhich the substituent 'or ssubstituents on the. amino group contain at least four conjugated carbon to carbon bonds in a cyclic nucleus.
  • the diazo compounds of this class are diazo derivatives of amines which may be represented by the for- '5'-(4-amlno-2-carboxyphenylamino)-quinollne-4-carboxyllc mulae:
  • R1 contains at least four conjugated carbon to carbondouble bonds innan aromatic orheterocyclic ring system
  • R2 is a heterocyclic trifiuoride, zinc chloride, cadmium chloride
  • naphthalene disulfonic acid and the like.
  • Diazo compounds of this class can be readily prepared by the diazotization of the corresponding amine and the formation of the diazo complex by the usual methods.
  • the diazo compound is applied to a suitable carrier such as paper, a regenerated cellulose. cellulose ester or cellu ose ethe s ip. a glass plate. textile.
  • diluent tforthe coating *solution-organic solvents of .high ,volatility-suchas alicohols, particularly isopropyl alcohol,.ethers-and.
  • ketones as for example, acetone
  • acetone may be employed either wholly or partially in place of the water, particularly when the film materials of re-.-
  • the diazo compound may be added to the coating solution as the only azo dye component and the solution coated onto the carrier in the same manner.
  • the exposure under a suitable positive or negative picture, drawing or the like is effected as before but the image is developed by bathingthe exposed element in an alkaline bath containing the azo dye coupler necessary to couple with the undecomposed diazo to form the. desired azo .dye in the unexposed areas.
  • any compound which will function as a coupling component may be employed either in the coating composition or with the-diazo compound as a two-component system or in thedeveloping solution as a color forming -develperto. be used with a single component -diazotype system.
  • thecoupling component selected will be one which willproduce the desired color or a combination of coupling componentswhich will produce a desired multi-color 'eiifect.
  • preferredcoupling, components are-the sodium salt of 2-amino-8-naphthol-3,fi-disulfonic acid,
  • the diazo-compounds of this invention are particularly sensitive-to long wave light of wave lengths greater than 4200' A. and as high as 6000l n, whichwave lengths are emitted by fluorescent lights, they are also sensitiveto'shorter wave length light, l and in 'view" of- "this dual sensitivity as compared with "diazo compounds "here-'- tofore employed in diazotype production, which latter do not enjoy the long wavesensitivitythe new diazo compounds permit "the utilization pt A
  • The. new diazo compounds also have the. ad
  • Example-1.+4 diczophenyl-anaphthylamine A mixture of 13.5 parts of 4-aminophenyla naphthylamine [prepared by the method of .J.
  • A' mixture of 1.0'part of the zinc chloride complex of 4-(a-naphthylamino) -benzenediazonium chloride, 1.5 parts citric acid, 1.5 parts thiourea, 50 parts water and 0.25 part ofv 3,5-dihydroxybenzoic acid is coated on rag sulfite paper, This coating shows sensitivity tolight, having wave lengths betwen 3250A. and 5200 A. with a maximum sensitivityof 4350 A. Thesevalues may be compared with the sensitivity .of p"-diethylaminobenzenediazonium chloride complex of zinc chloride, which is sensitive to light in the range of 3500-4600 A, with a mammum sensitivityat 4100 A.
  • the mixture is cooled to .3 G and 40 parts of molar sodium nitrite solutionfis added;; ;This' mixture isstirred for 18 hours and the excess nl: trite is destroyed by the addition of urea and the mixture is filtered. To the filtrate is added parts of-concentrated hydrochloric acidiand l8. partsof an 85% solution ofzinc chloride. fIhe mixture is cooled and filtered. A yellow-orange.
  • naphthalene-G-sulfonic acid 120 parts water, 30
  • a coated paper using diazotiz'ed aminq phenyl-B-naphthylamine as the light-sensitive 3 /2 minutes exposure to the fluorescent lampto' give a comparable print, i. e., the printing speed of the new material is nearly double that of the fastest diazotype material now produced when printed by means of a fluorescent light, as a source of long wave length light.
  • Example 4.N-(p-diazophenyl)-carbazole v To a hot solution of 29.4 parts of N-(p-aminophenyl) -carbazole [prepared by the'method of Helv. chim. Acta 6, 94101 (1923)] in 300 parts of formic acid was added 10.1 parts of concentrated hydrochloric acid. On cooling the solution to 10-15 0., a white precipitate was noted. To the suspension at 10 C. was added dropwise, over a period of 45 minutes, 21 parts '7. of 5 molar sodium nitrite solution. A trace of sulfamic 'acid'was added to destroy the excess ni trite. To the mixture was added 320 parts of a 10% solution of naphthalene-1,5-disulfonic acid.
  • a mixture of 11.7 parts of 2-(p-aminophenylamino) -quino1ine, 50 parts of water and 20 parts of concentrated hydrochloric acid is cooled to 0 C.
  • a solution of 3.5 parts of sodium nitrite and 7 parts of water is added dropwise over a period of minutes and the mixture stirred for an additional 30 minutes.
  • a yellow precipitate, which formed, is dissolved by adding 500 parts of absolute alcohol to the mixture.
  • the mixture is cooled to l0 C. and filtered.
  • the product. amounting to 13 parts, is purified by dissolving 6 parts of the material in 350 parts of water, cooling to 0 C. and adding 40 parts of 85% zinc chloride.
  • the brilliant yellow solid, which formed, is cooled and dried in vacuo.
  • a diazotype material comprising an insoluble support having a non-colloidal coating containing a light sensitive diazo derivative of a p-phenylenediamine of the following formulae:
  • R is a member of the group consisting of hydrogen, alkyl, and substituted alkyl
  • Y is a member of the group consisting of hydrogen, carboxyl and sulfonic acid radicals
  • R1 is a member of the group consisting of aromatic and heterocyclic radicals of the naphthalene, anthracene,
  • R2 is a heterocyclic ring system containing the N atom as a hetero atom selected from the group consisting of indole and carbazole ring systems.
  • a diazotype material comprising an insoluble support having a non-colloidal coating containing as the light sensitive agent a diazo derivative of 4-aminophenyl-u-naphthylamine having the structural formula:
  • a diazotype material comprising an insoluble support having a non-colloidal coating containing as the light sensitive agent a diazo derivative of N-(p-aminophenyl) -carbazole having the structural formula:

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Heat Sensitive Colour Forming Recording (AREA)
  • Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
US788656A 1947-11-28 1947-11-28 Diazotypes containing n-substituted p-diazoanilines having radicals of at least four conjugated c-c double bonds as n-substituents Expired - Lifetime US2605182A (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
BE486034D BE486034A (en, 2012) 1947-11-28
US788656A US2605182A (en) 1947-11-28 1947-11-28 Diazotypes containing n-substituted p-diazoanilines having radicals of at least four conjugated c-c double bonds as n-substituents
FR988975D FR988975A (fr) 1947-11-28 1948-11-22 Matériel d'impression diazotype

Applications Claiming Priority (1)

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US788656A US2605182A (en) 1947-11-28 1947-11-28 Diazotypes containing n-substituted p-diazoanilines having radicals of at least four conjugated c-c double bonds as n-substituents

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US2605182A true US2605182A (en) 1952-07-29

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FR (1) FR988975A (en, 2012)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20150307478A1 (en) * 2009-06-12 2015-10-29 Abivax Compounds useful for treating aids
US9827237B2 (en) 2013-07-05 2017-11-28 Abivax Compounds useful for treating diseases caused by retroviruses
US10253020B2 (en) 2009-06-12 2019-04-09 Abivax Compounds for preventing, inhibiting, or treating cancer, AIDS and/or premature aging
US11441181B2 (en) 2013-01-17 2022-09-13 Abivax miRNA-124 as a biomarker
US11649210B2 (en) 2014-07-17 2023-05-16 Abivax Use of quinoline derivatives for the treatment of inflammatory diseases
US11992499B2 (en) 2018-12-20 2024-05-28 Abivax Quinoline derivatives for use in the treatment of inflammation diseases

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1756400A (en) * 1926-02-22 1930-04-29 Kalle & Co Ag Light-sensitive materials and process of making them
US1758676A (en) * 1927-07-21 1930-05-13 Kalle & Co Ag Light-sensitive layers and process of preparing them
US1983005A (en) * 1927-05-14 1934-12-04 Zaiden Hojin Rikagaku Kenkyujo Positive sensitized paper
US2100063A (en) * 1931-12-09 1937-11-23 Kaile & Co Ag Process for the production of tanned pictures
US2277409A (en) * 1939-08-03 1942-03-24 Norton & Gregory Ltd Chemical composition

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1756400A (en) * 1926-02-22 1930-04-29 Kalle & Co Ag Light-sensitive materials and process of making them
US1983005A (en) * 1927-05-14 1934-12-04 Zaiden Hojin Rikagaku Kenkyujo Positive sensitized paper
US1758676A (en) * 1927-07-21 1930-05-13 Kalle & Co Ag Light-sensitive layers and process of preparing them
US2100063A (en) * 1931-12-09 1937-11-23 Kaile & Co Ag Process for the production of tanned pictures
US2277409A (en) * 1939-08-03 1942-03-24 Norton & Gregory Ltd Chemical composition

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10975063B2 (en) 2009-06-12 2021-04-13 Abivax Compound, and production method thereof, and methods of treatment using the compound
US9908869B2 (en) 2009-06-12 2018-03-06 Abivax Compounds useful for treating aids
US10017498B2 (en) * 2009-06-12 2018-07-10 Abivax Compounds useful for treating AIDS
US10253020B2 (en) 2009-06-12 2019-04-09 Abivax Compounds for preventing, inhibiting, or treating cancer, AIDS and/or premature aging
US10683284B2 (en) 2009-06-12 2020-06-16 Abivax Compounds for preventing, inhibiting, or treating cancer, aids and/or premature aging
US20150307478A1 (en) * 2009-06-12 2015-10-29 Abivax Compounds useful for treating aids
US11014918B2 (en) 2009-06-12 2021-05-25 Abivax Compounds and pharmaceutical compositions containing at least one of the compounds
US11441181B2 (en) 2013-01-17 2022-09-13 Abivax miRNA-124 as a biomarker
US9827237B2 (en) 2013-07-05 2017-11-28 Abivax Compounds useful for treating diseases caused by retroviruses
US11649210B2 (en) 2014-07-17 2023-05-16 Abivax Use of quinoline derivatives for the treatment of inflammatory diseases
US11649211B2 (en) 2014-07-17 2023-05-16 Abivax Use of quinoline derivatives for the treatment of inflammatory diseases
US12202804B2 (en) 2014-07-17 2025-01-21 Abivax In vitro or ex vivo methods for screening a quinoline derivative
US11992499B2 (en) 2018-12-20 2024-05-28 Abivax Quinoline derivatives for use in the treatment of inflammation diseases

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Publication number Publication date
BE486034A (en, 2012)
FR988975A (fr) 1951-09-03

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