US2529464A - Diazotype composition containing n-hydroxyethyl-m-toluidine-p-diazos - Google Patents

Diazotype composition containing n-hydroxyethyl-m-toluidine-p-diazos Download PDF

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Publication number
US2529464A
US2529464A US698874A US69887446A US2529464A US 2529464 A US2529464 A US 2529464A US 698874 A US698874 A US 698874A US 69887446 A US69887446 A US 69887446A US 2529464 A US2529464 A US 2529464A
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United States
Prior art keywords
diazo
diazotype
toluidine
light
coated
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Expired - Lifetime
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US698874A
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English (en)
Inventor
Glahn William H Von
Lester N Stanley
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GAF Chemicals Corp
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General Aniline and Film Corp
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Publication date
Application filed by General Aniline and Film Corp filed Critical General Aniline and Film Corp
Priority to US698874A priority Critical patent/US2529464A/en
Priority to GB25598/47A priority patent/GB642422A/en
Priority to FR953306D priority patent/FR953306A/fr
Priority to CH273427D priority patent/CH273427A/fr
Application granted granted Critical
Publication of US2529464A publication Critical patent/US2529464A/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
    • G03C1/54—Diazonium salts or diazo anhydrides

Definitions

  • This invention relates to the production of diazotype light-sensitive layers or other diazotype materials and more particularly to diazotype materials wherein the light-sensitive agent is a diazo derivative of a p-phenylene diamine compound having the following formula;
  • R is a member of the group consisting of hydrogen, methyl, ethyl and hydroxyethyl groups.
  • Such relatively fast coupling components include 2,3-dihydroxynaphthalene and acetoacetanilide which are highly desirable for use in the production of deep blue and black tones when coupled with suitable diazo compounds.
  • this fast coupling property of such azo components tends to increase the precoupling tendencies of the composition and, therefore, reduce the shelf life of they light-sensitive diazotype layer in which such components are employed. Consequently, unless such diazotypes are used by exposing and developing shortly after their manufacture, they will exhibit as a result of precoupling instability a background color which not only detracts from the appearance of the reproduction but reduces the contrast between the developed image and the background.
  • Such precoupling instability is a decided disadvantage in the production of diazotype intermediate transparencies since the background color resulting from precoupling of the dye components will absorb, actinic lightiin the background areas where the transparency should transmit the light. Since precoupling will not be uniform, the background of the final reproduction taken from the intermediate transparencywill obtain various degrees of exposure and will, consequently, be colored in varying depths of the sepia color. 1 Furthermore, the contrast of the intermediate transparency Will be considerably reduced by the background color rendering it more difilcult to detect flaws in the intermediate reproduction.
  • Diazo compounds of this class are stable compounds under ordinary conditions but decompose read: ily upon exposure to light to produce colorless non-coupling decomposition products. They thus provide the characteristic of photo-sen sitivity necessary to any diazo compound used for the production of diazotype copies.
  • An added advantage of the p-phenylene diamine diazo derivatives of the above-described class is the ability of these compounds to remain in a solution with the other components which are used in diazotype coating solutions and par ticularly in those cases where the coating solution is relatively concentrated, such as coating solutions for the production of intermediate transparencies or diazotype media for the copying of transparent microphotographs.
  • This factor is important since in the case of hitherto known diazos containing a methyl group ortho to the diazo group it is difficult to achieve practical concentrations of the diazo component in such diazotype coating solutions.
  • N diethyl m toluidine-p-diazonium chloride- ZnClz double salt or N-hydroxyethyl-N-furfurylm-toluidine-p-diazo-ZnCl2 double salt is used as the diazo component in a heavily loaded coating solution for intermediate foils and microphotographs, the diazo tends to precipitate out, thus impairing uniform penetration and producing a high surface concentration of the diazo. Due to the excellent solubility of p-phenylene diamine diazos of the above class, this disadvantage is overcome even in the case of the most concentrated coating solutions employed.
  • the base or support carrying or containing light-sensitive compounds, azo dye components and other coating mate-rials is coated, dipped, brushed or sprayed with the sensitizing solution by means known to the art, the particular type of application depending upon the carrier employed.
  • carriers such materials as paper or cloth, either of which may be opaque, semitransparent or of a transparentized type, or a film, such as prepared from cellulose nitrate, celluloseacetate or other cellulose esters or regenerated cellulose and the like, or a glass plate or sheet metal may be employed.
  • the coating solution is generally aplied by using a trough-and doctor blade but may, however, be brushed or or sprayed.
  • a film is used as the support, in order to obtain proper penetration swelling agents are added to the coating solution and the solution is applied by dipping.
  • the coating solution may contain the usual agents, such as metal salts de signed to intensify the dyestuif images, such as aluminum sulfate, titanium ammonium fluoride,
  • the diazo and azo components are applied to the support in combination and are then exposed to light under an inmage, followed by development with ammonia or other alkaline vapor, nevertheless, the invention is also applicable to the so-called moist development process.
  • the solution applied to the support contains as the only dye component the diazo compound of the class set forth above.
  • the coated support is exposed and the diazo decomposed in the exposed areas in the same manner as in the case of the two-component system but the unexposed areas are developed with a solution of alkaline agents containing the coupling component.
  • these diazos have the further advantage of producing sepia images of outstanding opacity to ultra violet light when they are used with couplers which will produce sepia shades, such as resorcinol, resorcinol sulfonic acid, dichlororesorcinol, 4-bromoresorcinol, 3-hydroxyphenoxy acetic acid, 3-acetaminophenol, 3-hydroxyphenyl guanide and 3-hydroxyphenyl bi-guanide.
  • couplers which will produce sepia shades, such as resorcinol, resorcinol sulfonic acid, dichlororesorcinol, 4-bromoresorcinol, 3-hydroxyphenoxy acetic acid, 3-acetaminophenol, 3-hydroxyphenyl guanide and 3-hydroxyphenyl bi-guanide.
  • Example 1 A transparent paper stock is coated with a solution containing per cc. of water:
  • Example 2 A transparent paper stock is coated with a solution containing per 100 cc. of water:
  • the diazotype coating of this example is found to have the same high degree of precoupling stability as the composition of Example 1 when compared with the same standards. It also has the same solubility, ease of coating and penetration qualities as Example l and produces upon exposure and development a dark sepia print having excellent visual density and the same high degree of photographic density or opacity to ultra violet light as the prints obtained in accordance with Example 1.
  • Emample 3 A transparent paper stock is coated with a solution containing per 100 cc. of water:
  • the paper coated in accordance with the formula of this example also has the same high degree of precoupling stability as that of Example 1 in comparison with the same standards as were compared in Example 1. Its solubility, coating and penetration properties are also excellent in comparison With the named standards of Example 1. Upon exposure under an image and subsequent development by contact with ammonia, a darkreddish sepia print is obtained which has excellent visual and photographic density. These prints make excellent intermediate or transition positives.
  • the combination of this example has particularly good properties for use in reflex printing wherein the translucent sheet coated as above is placed over an opaque original and light is transmitted through the translucent coated sheet to be reflected in part from the original thereby forming a latent positive image in the translucent sheet to be developed in the usual manner and used as an intermediate, if desired, for the production of further diazotype copies.
  • Example 4 A transparent paper stock is coated with a solution containing per cc. of water:
  • Example 5 A transparent paper stock is coated with a solution containing per 100 cc. of water:
  • Example 6 A regular paper stock is coated with a solution containing per 100 cc. of Water:
  • N-ethyl-N-hydroxyethyl-m-toluidine-pdiazo-ZnClz double salt 2.0 g. 2,3-dihydroxynaphthalene-6-sulfonic acid 0.5 g.
  • the thus coated paper has excellent stability to precoupling and can be stored for a much longer period of time than a paper similarly prepared from a coating solution containing similarly constituted di-azos which are unsubstituted in the position ortho to the diazo group, such as N-ethyl- N-hydroxyethylaniline-;p-diazo ZnClz double salt wherein coupling of the 2,3-dihydroxynaphthalene occurs in a relatively short time.
  • a coating solution containing similarly constituted di-azos which are unsubstituted in the position ortho to the diazo group, such as N-ethyl- N-hydroxyethylaniline-;p-diazo ZnClz double salt wherein coupling of the 2,3-dihydroxynaphthalene occurs in a relatively short time.
  • composition of this example also has a faster printing speed than similar compositions containing as the diazo compound N-ethyl-mtoluidine-p-diazo ZnCl double salt.
  • Example 7 A regular paper stock is coated with a solution containing per 100 cc. of water:
  • diazotype paper ha the same exceptional precoupling stability and fast printing properties as the diazotype paper of Examples 6 and 7 and yieldsupon exposure and development a maroon image of sharp contrast on a clear white background.
  • Example 1 Upon substituting in Example 1, 3.5v g. oi ibromoresorcinol; 3.0 g. 3-hydroxyphenoxyacetic acid; 2.8 g. 3-acetylaminophenol or 3.4 g. 1,3-dihydroxybenzene-5-sulfonic acid as the azo' dye component in place of the 2.2 g. of resorcinol used in Example 1, diazotype coatings having the-same superior properties as the coating of Example 1 are obtained.
  • the sepia dye image is a lighter tone than in the case of resorcinol or the resorcinol derivatives.
  • a diazotype photographic material comprising a light-sensitive diazonium salt of the compound having the formula: V

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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)
US698874A 1946-09-23 1946-09-23 Diazotype composition containing n-hydroxyethyl-m-toluidine-p-diazos Expired - Lifetime US2529464A (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
US698874A US2529464A (en) 1946-09-23 1946-09-23 Diazotype composition containing n-hydroxyethyl-m-toluidine-p-diazos
GB25598/47A GB642422A (en) 1946-09-23 1947-09-19 Diazotype compositions containing n-hydroxy-ethyl m-toluidine p-diazonium compounds
FR953306D FR953306A (fr) 1946-09-23 1947-09-23 Perfectionnements aux matériels photographiques diazotypes
CH273427D CH273427A (fr) 1946-09-23 1947-09-23 Matériel photographique diazotype.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US698874A US2529464A (en) 1946-09-23 1946-09-23 Diazotype composition containing n-hydroxyethyl-m-toluidine-p-diazos

Publications (1)

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US2529464A true US2529464A (en) 1950-11-07

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US (1) US2529464A (fr)
CH (1) CH273427A (fr)
FR (1) FR953306A (fr)
GB (1) GB642422A (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3462271A (en) * 1962-09-26 1969-08-19 Keuffel & Esser Co Diazotype material
US3498790A (en) * 1965-05-08 1970-03-03 Keuffel & Esser Co Diazotype material

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2929796A (en) * 1954-10-15 1960-03-22 Firestone Tire & Rubber Co Hydroxy-substituted phenylenediamines and their use in rubber
US4196145A (en) * 1973-10-15 1980-04-01 Clairol Incorporated Dyeing keratin fibers with 2-substituted m-toluenediamines

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2217189A (en) * 1938-12-05 1940-10-08 Kalle & Co Ag Process of preparing photographic prints
US2336309A (en) * 1941-05-29 1943-12-07 Eastman Kodak Co Diazotype photographic material

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2217189A (en) * 1938-12-05 1940-10-08 Kalle & Co Ag Process of preparing photographic prints
US2336309A (en) * 1941-05-29 1943-12-07 Eastman Kodak Co Diazotype photographic material

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3462271A (en) * 1962-09-26 1969-08-19 Keuffel & Esser Co Diazotype material
US3498790A (en) * 1965-05-08 1970-03-03 Keuffel & Esser Co Diazotype material

Also Published As

Publication number Publication date
GB642422A (en) 1950-09-06
CH273427A (fr) 1951-02-15
FR953306A (fr) 1949-12-05

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