US2429249A - Stabilized aryl diazo-n-sulfonate light-sensitive material - Google Patents

Stabilized aryl diazo-n-sulfonate light-sensitive material Download PDF

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Publication number
US2429249A
US2429249A US502466A US50246643A US2429249A US 2429249 A US2429249 A US 2429249A US 502466 A US502466 A US 502466A US 50246643 A US50246643 A US 50246643A US 2429249 A US2429249 A US 2429249A
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United States
Prior art keywords
diazo
solution
light
sulfonate
light sensitive
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
US502466A
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English (en)
Inventor
Glahn William Henry Von
Maximilian K Reichel
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GAF Chemicals Corp
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General Aniline and Film Corp
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Filing date
Publication date
Priority to FR959577D priority Critical patent/FR959577A/fr
Application filed by General Aniline and Film Corp filed Critical General Aniline and Film Corp
Priority to US502466A priority patent/US2429249A/en
Application granted granted Critical
Publication of US2429249A publication Critical patent/US2429249A/en
Priority to GB34476/47A priority patent/GB641276A/en
Priority to CH277044D priority patent/CH277044A/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • 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
    • G03C1/56Diazo sulfonates

Definitions

  • This invention relates to the production of diazotype light sensitive layer wherein the lightsensitive agent is an aryl diazo-N-sulfonate and more particularly to the improvement of the stability and printing speed of such diazotype light sensitive layers.
  • Reproduction media for the photoprinting of transparent or semi-transparent originals in which media the photosensitive material is a diazo compound are well known. They are generally produced by treating the surface of a suitable base, such as paper, with a solution of two dye components, one of which, the diazo component, is the photosensitive body and the other, known as the azo component or coupling component, is a compound capable of reacting under suitable conditions with the diazo component to form a dye.
  • the diazo component of such a light sensitive layer decomposes upon exposure to light to a compound which can no longer combine with the coupling component to form a dye.
  • 2,217,189 do not have as long a shelf life as the ammonia developable light sensitive layers coated with a solution of a diazo compound and an azo component. Furthermore, the coating solution is unstable and precipitates colored material after a short time which renders it un- This instability of the coating solution and shelf life of the coated paper can be improved by adding a quantity of sodium bisulfite to the coating solution as recommended in the patent. However, if sufficient 'sodium bisulfite is added to accomplish a commercially desirable stability and shelf life, the speed of printing by exposure to light is so retarded as to render the light sensitive layer unsuitable for any practical purpose.
  • the coating solution can be sufficiently stabilized for all practical purposes and that the shelf life of the coated paper can be improved to an extent comparable with ammonia developable diazotype layers by adding ketones, ketonic acids or aromatic aldehydes or their substitution products, which will form addition products with bisulfites to the coating solution containing the diazo-N-sulfonate derived from a p-phenylene diamine, an
  • ketonic acid is desirlight sensitive layer by adding at least molecularly equivalent amounts of the ketone, ketonic acid or aromatic aldehyde.
  • Coating solutions which are stable for several days under ordinary ticularly adaptable to this process: Acetone, ketopentamethylene, cyclohexanone. acetonyl acetone, furfuraldehyde, levulinic acid, pyruvic acid, aceto acetic acid alkyl esters and benzaldehyde. It will be understood that the classification ketonic acids includes salts of such acids and their esters.
  • a coating solution was prepared by stirring into solutionin 1,000 cc. of water:
  • a zinc acetate precoated paper was coated with the above solution and dried in the usual manner. Samples of this coated paper were then exposed to light. under adiapositive and the thus exposed sensitized samples were developed by contact with heat. Qther samples of the unexposed, but coated paper together with the exposed and developed samples were then stored for the purpose of determining the stability of the light sensitive layer of the finished print. Similar tests were made at the same time on the same type of paper coated with a solution containing the same components as above with the exception of thebenzaldehyde. It was observed that the printing speed and stability of the papers coated with. the solution containing the benzaldehyde were far greater than the printing speed and stability of papers coated with the same solutionlacking. the benzaldehyde.
  • a coating solution was prepared by stirring into solution in 1,000 cc. of water:
  • Zinc acetate precoated paper samples were coated with this solution and dried in the usual manner. The same tests were made as i th e Of Example 1 and the. results compared with the results obtained from a paper coated with the same solution but omitting the acetone. It was found that the stability and light sensitivity or printing speed of paper coatings made with the solution of this example have the same improved characteristics as compared with the characteristics of the paper coated with the same solution lacking the acetone as were observed in the case of. Example I.
  • a coating solution was prepared by stirring into solution in 950 cc. of water:
  • Example II The resulting solution was coated on zinc acetate precoated paper and the coatings dried in the usual manner. Samples of these coatings were. then tested for stability'and sensitivity to light by exposing same'under a diapositive and developing the exposed light sensitive layers by heating. The thus exposed and developed prints and samples of unexposedcoatings were stored in the same manner as in Example I. It was found that the papers coated with the solution of this example had excellent characteristics as to stability and light sensitivity and showed a marked improvement over samples prepared from the same solution, but omitting the acetonyl acetone.
  • a coating solution- was prepared by stirring into. solution in 950 cc. of water:
  • a light sensitive layer on a suitable base comprising a mono diazo-N-sulfonate derivative of a p-phenylene diamine, an azo component, an alkali metal bisulfite, and a member of the group consisting of ketones, ketonic acids, and aromatic aldehydes Which form addition products withbisulfites.
  • a light sensitive layer on a suitable base comprising a mono diazo-N-sulfonate derivative of p-phenylene diamine, an azo component, and an addition product of an alkali metal bisulfite with a member of the group consisting of ketones, ketonic acids and aromatic aldehydes which form addition products With bisulfites.
  • a light sensitive layer on a suitable base comprising a mono diazo-N-sulfonate derivative of a p-phenylene diamine, an azo component, an alkali metal bisulfite and benzaldehyde.
  • a light sensitive layer on a suitable base comprising a mono diazo-N-sulfonate derivative of a p-phenylene diamine, an azo component, an alkali metal bisulfite and acetone.
  • a light sensitive layer on a suitable base comprising amono diazo-N-sulfonate derivative 01 a p-phenylene diamine, an azo component, an alkali metal bisulfite and pyruvic acid.

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  • Chemical & Material Sciences (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)
US502466A 1943-09-15 1943-09-15 Stabilized aryl diazo-n-sulfonate light-sensitive material Expired - Lifetime US2429249A (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
FR959577D FR959577A (nl) 1943-09-15
US502466A US2429249A (en) 1943-09-15 1943-09-15 Stabilized aryl diazo-n-sulfonate light-sensitive material
GB34476/47A GB641276A (en) 1943-09-15 1947-12-29 Stabilized aryl diazo-n-sulfonate light sensitive material
CH277044D CH277044A (fr) 1943-09-15 1948-02-10 Produit diazotype sensible à la lumière.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US502466A US2429249A (en) 1943-09-15 1943-09-15 Stabilized aryl diazo-n-sulfonate light-sensitive material

Publications (1)

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US2429249A true US2429249A (en) 1947-10-21

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US502466A Expired - Lifetime US2429249A (en) 1943-09-15 1943-09-15 Stabilized aryl diazo-n-sulfonate light-sensitive material

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US (1) US2429249A (nl)
CH (1) CH277044A (nl)
FR (1) FR959577A (nl)
GB (1) GB641276A (nl)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2653091A (en) * 1950-01-31 1953-09-22 Rca Corp Photographic diazotype composition and heat development thereof
US2694009A (en) * 1948-10-01 1954-11-09 Keuffel & Esser Co Diazo-n-sulfonate light-sensitive material
US2732299A (en) * 1952-07-22 1956-01-24 Light sensitive
US3113865A (en) * 1960-05-05 1963-12-10 Eastman Kodak Co Heat developable diazo sulfones
US3140180A (en) * 1959-04-29 1964-07-07 Keuffel & Esser Co Heat developable diazotype reproduction coatings comprising thermolabile carboxylic tertiary alkyl esters
US3453112A (en) * 1959-11-23 1969-07-01 Bauchet & Cie Ets Heat-developable diazotype material
US3607287A (en) * 1968-12-30 1971-09-21 Keuffel & Esser Co Negative-working two-component diazosulfonate material
US3713825A (en) * 1970-04-27 1973-01-30 Plastic Coating Corp Light-activated diazography
US4403028A (en) * 1981-01-26 1983-09-06 Andrews Paper & Chemical Co., Inc. Light sensitive diazonium salts and diazotype materials
US4419432A (en) * 1982-09-22 1983-12-06 Keuffel & Esser Company Diazotype composition stabilization

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS62253157A (ja) * 1986-04-25 1987-11-04 Sharp Corp 感熱記録体を用いた複写方法

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1483797A (en) * 1923-03-20 1924-02-12 British Dyestuffs Corp Ltd Dyeing and printing acetyl silk and materials containing it
GB294972A (en) * 1927-05-03 1928-08-03 Frans Van Der Grinten Improvements in the manufacture of diazo-types
US1973148A (en) * 1934-09-11 Products adapted fob the produc
DE677685C (de) * 1936-03-04 1939-09-12 Hans Th Bucherer Dr Verfahren der Diazotypie
US2217189A (en) * 1938-12-05 1940-10-08 Kalle & Co Ag Process of preparing photographic prints

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1973148A (en) * 1934-09-11 Products adapted fob the produc
US1483797A (en) * 1923-03-20 1924-02-12 British Dyestuffs Corp Ltd Dyeing and printing acetyl silk and materials containing it
GB294972A (en) * 1927-05-03 1928-08-03 Frans Van Der Grinten Improvements in the manufacture of diazo-types
DE677685C (de) * 1936-03-04 1939-09-12 Hans Th Bucherer Dr Verfahren der Diazotypie
US2217189A (en) * 1938-12-05 1940-10-08 Kalle & Co Ag Process of preparing photographic prints

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2694009A (en) * 1948-10-01 1954-11-09 Keuffel & Esser Co Diazo-n-sulfonate light-sensitive material
US2653091A (en) * 1950-01-31 1953-09-22 Rca Corp Photographic diazotype composition and heat development thereof
US2732299A (en) * 1952-07-22 1956-01-24 Light sensitive
US3140180A (en) * 1959-04-29 1964-07-07 Keuffel & Esser Co Heat developable diazotype reproduction coatings comprising thermolabile carboxylic tertiary alkyl esters
US3453112A (en) * 1959-11-23 1969-07-01 Bauchet & Cie Ets Heat-developable diazotype material
US3113865A (en) * 1960-05-05 1963-12-10 Eastman Kodak Co Heat developable diazo sulfones
US3607287A (en) * 1968-12-30 1971-09-21 Keuffel & Esser Co Negative-working two-component diazosulfonate material
US3713825A (en) * 1970-04-27 1973-01-30 Plastic Coating Corp Light-activated diazography
US4403028A (en) * 1981-01-26 1983-09-06 Andrews Paper & Chemical Co., Inc. Light sensitive diazonium salts and diazotype materials
US4419432A (en) * 1982-09-22 1983-12-06 Keuffel & Esser Company Diazotype composition stabilization

Also Published As

Publication number Publication date
CH277044A (fr) 1951-08-15
GB641276A (en) 1950-08-09
FR959577A (nl) 1950-03-31

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