US2416773A - Stabilized diazotype photoprinting materials - Google Patents

Stabilized diazotype photoprinting materials Download PDF

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Publication number
US2416773A
US2416773A US571352A US57135245A US2416773A US 2416773 A US2416773 A US 2416773A US 571352 A US571352 A US 571352A US 57135245 A US57135245 A US 57135245A US 2416773 A US2416773 A US 2416773A
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Prior art keywords
light
coating
sulfo
acid
sensitive
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US571352A
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Maximilian K Reichel
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GAF Chemicals Corp
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General Aniline and Film Corp
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Priority to US571352A priority Critical patent/US2416773A/en
Priority to GB29263/46A priority patent/GB617451A/en
Priority to CH265220D priority patent/CH265220A/en
Priority to FR938841D priority patent/FR938841A/en
Application granted granted Critical
Publication of US2416773A publication Critical patent/US2416773A/en
Priority to DEP29350A priority patent/DE869007C/en
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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
    • G03C1/60—Compositions containing diazo compounds as photosensitive substances with macromolecular additives

Definitions

  • This invention relates to the stabilization of photo-printing materials having light sensitive layers which are produced by the incorporation of a diazo compound as the light-sensitive medium onto the surface of a suitable carrier base. More particularly, it refers to the stabilization of so-called dry-development diazotype light-sensitive layers wherein the diazo compound is incorporated into the light sensitive layer together with an azo dyestufi coupling component.
  • diazo compounds for such dry-development or two-component diazotype light-sensitive layers the most suitable have been found to be those which are derived from orthoor para-aminonaphthols or aromatic paradiamines, particularly N-monoor di-substituted aromatic paradiamines.
  • Various processes are known for the preparation of light-sensitive layers which depend upon the use of a diazo compound as the light-sensitive medium, and various materials have been employed for the carrier of the light-sensitive layer, including textiles, paper, cellulosic films, and glass and metal surfaces.
  • the sensitized carrier is exposed to light under a transparent original which it is desired to reproduce and the diazo compound is decomposed in the areas unprotected by the outline of the original.
  • the undecomposed diazo compound in the protected areas is then used to develop'the image of the original by coupling the said diazo compound in an alkaline atmosphere with an azo dyestuff coupling component.
  • the development of the dyestuff forming the image is effected by bringing the exposed light-sensitive layer into contact with gaseous ammonia. This is known as the dry developing process.
  • the dyestuif components, as applied on the carrier are relatively unstable and cannot be stored for long periods prior to use.
  • the lightsensitive layers which carry the coupling component as well as the diazo compound in the light-sensitive layer are subject to premature coupling of the said dyestuif components as well as decomposition of the diazo compound upon long storage.
  • coating solutions and the light-sensitive layers prepared therefrom can be l5 ortho-hydroxy-carboxylic acids of the benzene or naphthalene series. 7
  • Diazotype light-sensitive layers which have been stabilized by addition of compounds of the above classshow greatly improved keeping qualities and are stable against decomposition or deterioration for much longer periods of storage than hitherto possible when using the same diazo light-sensitive compositions without these sta-
  • the following examples illustratethe invention but they are not intended to limit it thereto. The parts are by weight unless otherwise stated.
  • Example 1 A coating solution (A) was made up as follows:
  • Another coating solution (B) was made up containing the same ingredients as in (A) except that parts citric acid and 44 parts 5-sulio-salicylic acid were substituted for the 100 parts of citric acid. These solutions were then separately spread on strips 59' of paper, fabric, and film by the usual coating,
  • Example 2 The composition of the coating solutions A and B was the same as in Example 1, but as a stabilizer 47 parts 5-sulfo-o-cresotic acid per liter were used instead of the 5-sulfo-salicylic acid.
  • the coatings of A and B and the storage and test ing procedures were the same as in Example 1.
  • the stability of the coating. made according to this example was found to be superior to that of the coating made from a solution not containacid in the ing 5-sulfo-o-cresotic acid as a stabilizer.
  • Example 3 The composition of the coating solutions A and B was the same as in Example 1, but as a stabilizer 53.5 parts of 8-sulfo-2-hydroxy-3-naphthalene-carboxylic acid per liter were used instead of the 5-sulfo-salicylic acid.
  • Example 1 The stability of the coating made according to this example was found to be superior to that of the coating made from solution A not containing ,8-sulfo 2 hydroxy-3-naphthalene-carboxylic acid as a stabilizer.
  • Example 4 A coating solution was made up as follows:
  • solution A Sodium salt of the naphthalene-1,3,6-trisulfonic acid Aluminum sulfate were d ssolved in 1000 cc. of water (solution A)
  • Another coating solution (B) was made up containing the same ingredients as in solution (A). except that ,50 parts citric acid and 44 parts of 5-sulfo-salicylic acid were substituted for the 100 partsiof citric acid. Solutions A and B were then separately spread on strips of paper, fabric, and film by the usual coating method in the same manner as described in Example 1.
  • the lightsensitive layer thus produced was then stored at room temperature for several months and its stability then tested by observing the appearance of color in the light-sensitive layer due to premature coupling of the dye components and by comparison of its light-sensitive qualities with those of a testsample prepared and treated in the same manner as the light-sensitive layer of this example. but omitting the 5-sulfo-salicylic acid as a stabilizer. When so tested, it was found that the light-sensitive layer made in accordance with light-sensitive layers.
  • this example shows no discoloration due to premature coupling of the dye components after the storage period, whereas, the light-sensitive layer not having the 5-sulfo-salicylic acid as a stabilizing agent, under the same conditions, shows a' considerable amount of coloring, due to premav ture coupling.
  • Example 5 A coating solution was made up as follows:
  • Example 7 A coating solution was made up as follows:
  • Example 8 lene carboxylic acid per liter were used instead of the 5-sulfo-o-cresotic acid.
  • the coating, storage and testing procedures are the same as in Example 1.
  • the stability of the coating made according to this example was found to be superior to that of the coating made from solution A not containing 6-sulfo-2-hydroxy 3 naphthalenecarboxylic acid as a stabilizer.
  • Photoprinting materials comprising light sensitive layers on a suitable base containing in the light-sensitive layer a diazo compound suitable for forming a stable two-component diazotype layer, an azo dye coupling component and a member of the class consisting of sulfonated ortho-hydroxy-carboxylic acids of the benzene and naphthalene series.
  • Photoprinting materials comprising lightsensitive layers on a suitable base containing in the light-sensitive layer a diazo compound derived from an aromatic paradiaminean azo dye coupling component and a member of the class consisting of sulfonated ortho-hydroxy-carboxylic acids of the benzene and naphthalene series.
  • Photoprinting materials comprising lightsensitive layers on a suitable base containing in the light-sensitive layer a diazo compound derived from an ortho-aminonaphthol compound, an azo dye coupling component and a member of 6 the class consisting of sulfonated ortho-hydroxycarboxylic acids of the benzene and naphthalene series.
  • Photoprinting materials comprising lightsensitive layers on a suitable base containing in the light-sensitive layer a diazo compound derived from an aromatic paradiamine, an azo dye coupling component and 5-sulfo-salicylic acid.
  • Photoprinting materials comprising lightsensitive layers on a suitable base containing in the light sensitive layer a diazo compound derived from an aromatic paradiamine, an azo dye coupling component and 8-sulfo-2-hydroxy-3- naphthalene-carboxylic acid.
  • Photoprinting materials comprising lightsensitive layers on a suitable base containing in the light-sensitive layer, a diazo compound derived from an ortho-aminonaphthol compound, an azo dye coupling component and 5-su1fo-ocresotic acid.

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  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (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)

Description

Patented Mar. 4, 1947 UNITED STATES PATENT OFFICE Maximilian K. Reichel, Easton, Ia'.., assignor to General Aniline & Film Corporation, New York,
N. Y., a corporation of Delaware No Drawing. Application January 4, 1945,
' Serial No. 571,352,
6 Claims.
This invention relates to the stabilization of photo-printing materials having light sensitive layers which are produced by the incorporation of a diazo compound as the light-sensitive medium onto the surface of a suitable carrier base. More particularly, it refers to the stabilization of so-called dry-development diazotype light-sensitive layers wherein the diazo compound is incorporated into the light sensitive layer together with an azo dyestufi coupling component. As diazo compounds for such dry-development or two-component diazotype light-sensitive layers, the most suitable have been found to be those which are derived from orthoor para-aminonaphthols or aromatic paradiamines, particularly N-monoor di-substituted aromatic paradiamines.
Various processes are known for the preparation of light-sensitive layers which depend upon the use of a diazo compound as the light-sensitive medium, and various materials have been employed for the carrier of the light-sensitive layer, including textiles, paper, cellulosic films, and glass and metal surfaces. The sensitized carrier is exposed to light under a transparent original which it is desired to reproduce and the diazo compound is decomposed in the areas unprotected by the outline of the original. The undecomposed diazo compound in the protected areas is then used to develop'the image of the original by coupling the said diazo compound in an alkaline atmosphere with an azo dyestuff coupling component.
In the two-component layers which contemplate the incorporation of the coupling component into the light-sensitive layer with the diazo compound, the development of the dyestuff forming the image is effected by bringing the exposed light-sensitive layer into contact with gaseous ammonia. This is known as the dry developing process. The dyestuif components, as applied on the carrier are relatively unstable and cannot be stored for long periods prior to use. The lightsensitive layers which carry the coupling component as well as the diazo compound in the light-sensitive layer are subject to premature coupling of the said dyestuif components as well as decomposition of the diazo compound upon long storage.
Many attempts have been made to obtain more stable coating solutions and to render the lightsensitive layers produced therefrom less sensitive to deterioration without impairing the lightsensitive qualities of the diazo compound upon which the production of accurate images from the 30 bilizers.
2 original depends. These attempts have hitherto been relatively unsuccessful. It is therefore the object of this invention to provide coating solutions and light-sensitive layers, using diazo com- 5 pounds as the light-sensitive medium which can be stored for long periods prior to use and will be stable during storage, even under unfavorable conditions.
I have found that coating solutions and the light-sensitive layers prepared therefrom can be l5 ortho-hydroxy-carboxylic acids of the benzene or naphthalene series. 7
Examples of such compounds are:
5-sulf0-Salicy1ic acid B-sulfo-o-cresotic acid 6-su1fo-2hydroxy-3-naphtha1ene-carboxylic acid 8-sulfo-2-hydroxy-3-naphtha1ene-carboxylic acid Diazotype light-sensitive layers which have been stabilized by addition of compounds of the above classshow greatly improved keeping qualities and are stable against decomposition or deterioration for much longer periods of storage than hitherto possible when using the same diazo light-sensitive compositions without these sta- The following examples illustratethe invention but they are not intended to limit it thereto. The parts are by weight unless otherwise stated.
Example 1 A coating solution (A) was made up as follows:
were dissolved in 100 cc. of water. Another coating solution (B) was made up containing the same ingredients as in (A) except that parts citric acid and 44 parts 5-sulio-salicylic acid were substituted for the 100 parts of citric acid. These solutions were then separately spread on strips 59' of paper, fabric, and film by the usual coating,
method for the production of diazo-type lightsensitive layers, using a doctor blade to insure a thin even coating. After storage at room temperature for several months, the stability of the sensitized materials of A and B was tested by example, is superior to that of the sample which does not contain the 5-sulfo-salicylic light-sensitive layer.
Example 2 The composition of the coating solutions A and B was the same as in Example 1, but as a stabilizer 47 parts 5-sulfo-o-cresotic acid per liter were used instead of the 5-sulfo-salicylic acid. The coatings of A and B and the storage and test ing procedures were the same as in Example 1. The stability of the coating. made according to this example was found to be superior to that of the coating made from a solution not containacid in the ing 5-sulfo-o-cresotic acid as a stabilizer.
Erample 3 The composition of the coating solutions A and B was the same as in Example 1, but as a stabilizer 53.5 parts of 8-sulfo-2-hydroxy-3-naphthalene-carboxylic acid per liter were used instead of the 5-sulfo-salicylic acid. The coating,
storage, and testing procedures were the same as in Example 1. The stability of the coating made according to this example was found to be superior to that of the coating made from solution A not containing ,8-sulfo 2 hydroxy-3-naphthalene-carboxylic acid as a stabilizer.
, Example 4 A coating solution was made up as follows:
i V V 7 Parts Zinc chloride double salt of the diazo compound obtained from N,N-dimethy1-p-,
phenylenediamine 12.5 Citric acid 100 2,3-dihydroxy-naphthalene 5.9 Thiourea 45.0
Sodium salt of the naphthalene-1,3,6-trisulfonic acid Aluminum sulfate were d ssolved in 1000 cc. of water (solution A) Another coating solution (B) was made up containing the same ingredients as in solution (A). except that ,50 parts citric acid and 44 parts of 5-sulfo-salicylic acid were substituted for the 100 partsiof citric acid. Solutions A and B were then separately spread on strips of paper, fabric, and film by the usual coating method in the same manner as described in Example 1. The lightsensitive layer thus produced was then stored at room temperature for several months and its stability then tested by observing the appearance of color in the light-sensitive layer due to premature coupling of the dye components and by comparison of its light-sensitive qualities with those of a testsample prepared and treated in the same manner as the light-sensitive layer of this example. but omitting the 5-sulfo-salicylic acid as a stabilizer. When so tested, it was found that the light-sensitive layer made in accordance with light-sensitive layers.
this example shows no discoloration due to premature coupling of the dye components after the storage period, whereas, the light-sensitive layer not having the 5-sulfo-salicylic acid as a stabilizing agent, under the same conditions, shows a' considerable amount of coloring, due to premav ture coupling.
Example 5 Example 6 A coating solution was made up as follows:
- Parts Zinc chloride double salt of the diazo compound obtained from N ,N-diethyl-p-phenylene-diamine 14 Citric acid 1-phenyl-3-methyl-pyrazolone 8 Thiourea 45 were dissolved in 1000 cc. of water (solution A) Another coating solution (B) was made up containing the same ingredients as in solution A except that 50 parts of citric acid and 47 parts of 5-sulfo-o-cresotic acid were substituted for the 100 parts of citric acid. Solutions A and Bare then separately spread on strips of paper, fabric, and film by the usual coating method in the same manner as described in Example 1. The lightsensitive layer thus produced was then stored at room temperature for several months and its stability then tested in the same manner as in Example 1. The stability of the coating made according to this example was found to be superior to that of the coating made from a solution (A),
-' not containing 5-sulfo-o-cresotic acid.
Example 7 A coating solution was made up as follows:
Parts 2.1 diazo-hydroxy-naphthalene-5-sulfonic acid 14.0 Citric acid 100 Nickel sulfat 31.5 Phloroglucine 4.9 Thiourea 20.0
were dissolved in 1000 cc. of water (solution A). Another coating solution (B) was made up containing the same ingredients except that 50 parts of citric acid and 47 parts of 5-su1fo-o-cresotic acid were substituted for the 100 parts of citric acid. These solutions are then separately spread on strips of paper, fabric, and film by the-usual coating method, for the production of diazo-type The storage and testing procedures were the same as in Example 1. The stability of the coatings made according to this example were found to be superior to that of they coating made from solution A not containing 5- sulfo-o-cresotic acids as a stabilizer.
Example 8 lene carboxylic acid per liter were used instead of the 5-sulfo-o-cresotic acid. The coating, storage and testing procedures are the same as in Example 1. The stability of the coating made according to this example was found to be superior to that of the coating made from solution A not containing 6-sulfo-2-hydroxy 3 naphthalenecarboxylic acid as a stabilizer.
Having now fully described my invention and having set forth the best manner in which to practice it, What I claim as new is:
1. Photoprinting materials comprising light sensitive layers on a suitable base containing in the light-sensitive layer a diazo compound suitable for forming a stable two-component diazotype layer, an azo dye coupling component and a member of the class consisting of sulfonated ortho-hydroxy-carboxylic acids of the benzene and naphthalene series.
2. Photoprinting materials comprising lightsensitive layers on a suitable base containing in the light-sensitive layer a diazo compound derived from an aromatic paradiaminean azo dye coupling component and a member of the class consisting of sulfonated ortho-hydroxy-carboxylic acids of the benzene and naphthalene series.
3. Photoprinting materials comprising lightsensitive layers on a suitable base containing in the light-sensitive layer a diazo compound derived from an ortho-aminonaphthol compound, an azo dye coupling component and a member of 6 the class consisting of sulfonated ortho-hydroxycarboxylic acids of the benzene and naphthalene series.
4. Photoprinting materials comprising lightsensitive layers on a suitable base containing in the light-sensitive layer a diazo compound derived from an aromatic paradiamine, an azo dye coupling component and 5-sulfo-salicylic acid.
5. Photoprinting materials comprising lightsensitive layers on a suitable base containing in the light sensitive layer a diazo compound derived from an aromatic paradiamine, an azo dye coupling component and 8-sulfo-2-hydroxy-3- naphthalene-carboxylic acid.
6. Photoprinting materials comprising lightsensitive layers on a suitable base containing in the light-sensitive layer, a diazo compound derived from an ortho-aminonaphthol compound, an azo dye coupling component and 5-su1fo-ocresotic acid.
MAXIMILIAN K. REICHEL.
REFERENCES CITED The following references are of record in the file of this patent:
UNITED STATES PATENTS Schmidt et a1. Feb. 16, 1932
US571352A 1945-01-04 1945-01-04 Stabilized diazotype photoprinting materials Expired - Lifetime US2416773A (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
US571352A US2416773A (en) 1945-01-04 1945-01-04 Stabilized diazotype photoprinting materials
GB29263/46A GB617451A (en) 1945-01-04 1946-10-01 Stabilized photoprinting materials and process of producing them
CH265220D CH265220A (en) 1945-01-04 1946-11-14 Solution intended for the formation of sensitive diazotype layers for the printing of photocopies.
FR938841D FR938841A (en) 1945-01-04 1946-11-26 Improvements to equipment for photographic printing
DEP29350A DE869007C (en) 1945-01-04 1949-03-01 Stabilized blueprint material for the diazotype process

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US571352A US2416773A (en) 1945-01-04 1945-01-04 Stabilized diazotype photoprinting materials

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CH (1) CH265220A (en)
DE (1) DE869007C (en)
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GB (1) GB617451A (en)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2545057A (en) * 1946-06-12 1951-03-13 Gen Aniline & Film Corp Diazotypes containing resorcinol sulfonic acids as coupling components
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
US3944422A (en) * 1969-09-01 1976-03-16 Mita Industrial Company Limited Photosensitive material in use for diazo-type multicolor reproduction
US4403028A (en) * 1981-01-26 1983-09-06 Andrews Paper & Chemical Co., Inc. Light sensitive diazonium salts and diazotype materials
EP0277273A1 (en) * 1987-01-08 1988-08-10 Andrews Paper and Chemical Co., Inc. Diazotype compositions
US5106718A (en) * 1988-10-20 1992-04-21 Ciba-Geigy Corporation Positive photoresist composition containing alkali-soluble phenolic resin, photosensitive quinonediazide compound and sulfonyl containing compound

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ZA6706181B (en) * 1966-10-18

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1760780A (en) * 1927-09-06 1930-05-27 Kalle & Co Ag Light-sensitive layers and process of preparing them
US1811029A (en) * 1927-12-10 1931-06-23 Kalle & Co Ag Process of preparing light-sensitive layers by means of diazo compounds and the products obtainable thereby
US1845989A (en) * 1928-11-03 1932-02-16 Kalle & Co Ag Light-sensitive layers and process of preparing them

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1760780A (en) * 1927-09-06 1930-05-27 Kalle & Co Ag Light-sensitive layers and process of preparing them
US1811029A (en) * 1927-12-10 1931-06-23 Kalle & Co Ag Process of preparing light-sensitive layers by means of diazo compounds and the products obtainable thereby
US1845989A (en) * 1928-11-03 1932-02-16 Kalle & Co Ag Light-sensitive layers and process of preparing them

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2545057A (en) * 1946-06-12 1951-03-13 Gen Aniline & Film Corp Diazotypes containing resorcinol sulfonic acids as coupling components
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
US3944422A (en) * 1969-09-01 1976-03-16 Mita Industrial Company Limited Photosensitive material in use for diazo-type multicolor reproduction
US4403028A (en) * 1981-01-26 1983-09-06 Andrews Paper & Chemical Co., Inc. Light sensitive diazonium salts and diazotype materials
EP0277273A1 (en) * 1987-01-08 1988-08-10 Andrews Paper and Chemical Co., Inc. Diazotype compositions
US5106718A (en) * 1988-10-20 1992-04-21 Ciba-Geigy Corporation Positive photoresist composition containing alkali-soluble phenolic resin, photosensitive quinonediazide compound and sulfonyl containing compound

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Publication number Publication date
FR938841A (en) 1948-10-26
CH265220A (en) 1949-11-30
GB617451A (en) 1949-02-07
DE869007C (en) 1953-03-02

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