US2531091A - N-acetonyl-pyridinium chloride as an azo coupling component in diazotypes - Google Patents

N-acetonyl-pyridinium chloride as an azo coupling component in diazotypes Download PDF

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Publication number
US2531091A
US2531091A US686951A US68695146A US2531091A US 2531091 A US2531091 A US 2531091A US 686951 A US686951 A US 686951A US 68695146 A US68695146 A US 68695146A US 2531091 A US2531091 A US 2531091A
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United States
Prior art keywords
diazotypes
acetonyl
pyridinium chloride
coupling component
azo coupling
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Expired - Lifetime
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US686951A
Inventor
Andre E Van Dormael
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Gevaert Photo Producten NV
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Gevaert Photo Producten NV
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    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03CPHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C1/00Photosensitive materials
    • G03C1/52Compositions containing diazo compounds as photosensitive substances
    • G03C1/58Coupling substances therefor

Definitions

  • This invention relates to a process for preparing diazotypes.
  • the primary object of this invention is to provide a color coupler to be used in the preparation of diazotypes which is of great effectiveness.
  • R represents aryl, alkyl or aralkyl
  • X represents H, aryl, alkyl, aralkyl, acyl or a hydroaromatic residue
  • Y represents H, aryl, alkyl, aralkyl, acyl or a hydroaromatic residue.
  • I employ N- acetonyl-pyridinium chloride as a coupler.
  • my new coupling component is its great solubility and its quality of rapidly coupling and giving very intense dyestuffs with the usual diazo compounds.
  • the coupling element of my invention may be used singly or in any combination. Whenused in mixtures, diazotypes of very intense neutral color are obtained whereas, for instance, the use of phloroglucinol alone produces only a brown violet color.
  • EwampZe.-To a suitable paper is applied a solution of 1.5 g. of diazonium compound from p-diethylamino aniline, 1 g. of tartaric acid, 0.8 g. of aluminum sulphate, 0.15 g. of phloroglucinol and 0.08 g. of N-acetonylpyridinium chloride in cm. of water.
  • the paper is exposed through a diapositive and developed in an ammoniacal atmosphere.
  • the paper is exposed through a diapositive and developed in an ammoniacal atmosphere. A dark magenta print is obtained.
  • My new coupling component may be added either to the developer when the half-wet process is used, or to a solution which contains one or more diazo compounds and which is applied as light-sensitive layer to an adapted paper.
  • the method which comprises selectively exposing a lightsensitive material containing a light-sensitive diazo compound, and coupling the diazo compound retained in the unexposed areas with N- acetonyl-pyridinium chloride.

Description

Patented Nov. 21, 1950 N-AOETONYL-PYRIDINIUM CHLORIDE AS AN AZO CDUPLIN G COMPONENT EN DIAZO- TYPES Andre E. Van Dcrmael, Heverlee (Louvain), Bel- .gium,
assignor to Gevaert Photo-Producten N. V., Antwerp-Mortsel, Belgium, a company of Belgium No Drawing. Application July 29, 1946, Serial 1 Claim.
This invention relates to a process for preparing diazotypes.
The primary object of this invention is to provide a color coupler to be used in the preparation of diazotypes which is of great effectiveness.
Other objects will appear from the following description.
In diazotype processes, mono or polyhydroxy compounds as, for instance, resorcinol and phloroglucinol are chiefly used as coupling compounds.
It has also been proposed to use coupling components of the following formula:
wherein R represents aryl, alkyl or aralkyl; X represents H, aryl, alkyl, aralkyl, acyl or a hydroaromatic residue; and Y represents H, aryl, alkyl, aralkyl, acyl or a hydroaromatic residue.
All these coupling components produce with the usual diazo compounds dyestufis which form a more or less intense image. Regarding the second named group, it is said to offer the special advantage of being usable mixed with other components givin hereby opaque neutral colors.
It has been found that all organic compounds which contain a reactive methyl group are well suited as coupling components in the preparation of diazotypes, whereby known and commonly used diazo compounds may be "used as light-sensitive compounds.
According to this invention, I employ N- acetonyl-pyridinium chloride as a coupler.
The most important characteristics of my new coupling component is its great solubility and its quality of rapidly coupling and giving very intense dyestuffs with the usual diazo compounds.
The coupling element of my invention may be used singly or in any combination. Whenused in mixtures, diazotypes of very intense neutral color are obtained whereas, for instance, the use of phloroglucinol alone produces only a brown violet color.
The following example will serve to further In Belgium August 3, 1945 illustrate my invention but it is to be understood that this invention is not limited to the example iven.
EwampZe.-To a suitable paper is applied a solution of 1.5 g. of diazonium compound from p-diethylamino aniline, 1 g. of tartaric acid, 0.8 g. of aluminum sulphate, 0.15 g. of phloroglucinol and 0.08 g. of N-acetonylpyridinium chloride in cm. of water.
The paper is exposed through a diapositive and developed in an ammoniacal atmosphere. A
sharp black print is obtained.
The paper is exposed through a diapositive and developed in an ammoniacal atmosphere. A dark magenta print is obtained.
My new coupling component may be added either to the developer when the half-wet process is used, or to a solution which contains one or more diazo compounds and which is applied as light-sensitive layer to an adapted paper.
When used alone, it produces in both cases chiefly colored images. By using a mixture, it is possible to obtain all the desired colors and also practically complete neutral images.
Due to the great variety of my coupling component, all colors are obtainable and all coupling methods are usable so that multicolored images can easily be obtained.
I claim:
In the preparation of diazotypes, the method which comprises selectively exposing a lightsensitive material containing a light-sensitive diazo compound, and coupling the diazo compound retained in the unexposed areas with N- acetonyl-pyridinium chloride.
ANDRE E. VAN DORMAEL.
REFERENCES CITED The following references are of record in the file of this patent:
UNITED STATES PATENTS Num er Name Date 1,822,065 Sprongerts Sept. 8, 1931 2,027,229 Hinman Jan. '7, 1936 2,154,918 Schneider et a1. Apr. 18, 1939 2,217,189 Sus Oct. 8, 1940 2,331,326 Kendall Oct. 12, 1943 2,405,523 Sease Aug. 6, 1946
US686951A 1945-08-03 1946-07-29 N-acetonyl-pyridinium chloride as an azo coupling component in diazotypes Expired - Lifetime US2531091A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
BE266905X 1945-08-03

Publications (1)

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US2531091A true US2531091A (en) 1950-11-21

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US (1) US2531091A (en)
BE (1) BE459543A (en)
CH (1) CH266905A (en)
ES (1) ES176413A1 (en)
FR (1) FR931187A (en)
GB (1) GB617115A (en)
NL (1) NL62542C (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3307952A (en) * 1963-11-20 1967-03-07 Ibm Formation of diazo couplers in situ
US4130426A (en) * 1974-04-22 1978-12-19 Fuji Photo Film Co., Ltd. Heat developable light-sensitive diazotype materials and process of use

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE489248A (en) * 1948-11-05
DE966201C (en) * 1953-08-14 1957-07-18 Bayer Ag Process for the preparation of cyclohexanone oxime by catalytic hydrogenation of nitrocyclohexane salts

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1822065A (en) * 1928-10-19 1931-09-08 Kalle & Co Ag Azo dyestuff components and process of preparing them
US2027229A (en) * 1931-07-08 1936-01-07 Frederick Post Company Accelerated diazo printing and materials therefor
US2154918A (en) * 1937-07-30 1939-04-18 Agfa Ansco Corp Coupling compounds for color forming development
US2217189A (en) * 1938-12-05 1940-10-08 Kalle & Co Ag Process of preparing photographic prints
US2331326A (en) * 1939-07-22 1943-10-12 Ilford Ltd Production of colored photographic images
US2405523A (en) * 1944-08-09 1946-08-06 Du Pont Light-sensitive photographic compositions and elements

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1822065A (en) * 1928-10-19 1931-09-08 Kalle & Co Ag Azo dyestuff components and process of preparing them
US2027229A (en) * 1931-07-08 1936-01-07 Frederick Post Company Accelerated diazo printing and materials therefor
US2154918A (en) * 1937-07-30 1939-04-18 Agfa Ansco Corp Coupling compounds for color forming development
US2217189A (en) * 1938-12-05 1940-10-08 Kalle & Co Ag Process of preparing photographic prints
US2331326A (en) * 1939-07-22 1943-10-12 Ilford Ltd Production of colored photographic images
US2405523A (en) * 1944-08-09 1946-08-06 Du Pont Light-sensitive photographic compositions and elements

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3307952A (en) * 1963-11-20 1967-03-07 Ibm Formation of diazo couplers in situ
US4130426A (en) * 1974-04-22 1978-12-19 Fuji Photo Film Co., Ltd. Heat developable light-sensitive diazotype materials and process of use

Also Published As

Publication number Publication date
FR931187A (en) 1948-02-16
NL62542C (en)
GB617115A (en) 1949-02-01
CH266905A (en) 1950-02-28
BE459543A (en) 1900-01-01
ES176413A1 (en) 1948-07-01

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