DE1547921A1 - Photosensitive diazotype materials - Google Patents

Description

Photosensitive diazotype materials,

The present invention relates generally to photosensitive ones Diazotype materials and in particular light-sensitive diazotype materials, the dyes Contain, which after exposure and development, images of deep red-brown coloration and high tinting power result in the manufacture of Diazotype Rapid paper and as a color tint for the production of tracing papers with black lines immediate and " find practical use.

With the help of the Diaζοtypie process, a color image by coupling a component with a color image

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light-sensitive diazonium salt produced. A diazotype photosensitive material based on the above reaction generally contains a support or base material having a photosensitive diazonium salt which is destroyed and otherwise changed by exposure to light in the image-forming area, thereby preventing the reaction with the color-forming component. The image is thus generated in the unexposed area by the development, which triggers the coupling reaction and the azo-dye and thus the diazotype image is created. Since the .product of the coupling reaction is an azo dye _? Many color-forming components can be used to produce the desired spectral sensitivity distribution. In the production of the diazotype compositions, however, numerous difficulties have arisen so far in order that, after development, an image of high contrast density is formed in which the color formed by the coupling reaction has deeply colored tones of high color strength. Many of the difficulties identified above stem, in part, from the choice of coupling components which, while useful for producing certain hues, are limited in their use because the images produced thereby have poor color strength of the dye formed and low contrast density.

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The diazotype photosensitive materials of the present invention Invention produce after exposure and development Color images with high contrast density and high coloring power. They are characterized by deep red-brown Tints of high tinting power. A family of color formers Components have been found that, when coupled with the diazonium salts, provide high density and dyes high coloring power.

The deep red-brown in the coupling with diazonium salts Coupling components which produce tints of high tinting power are 2-halo-resorcinols, which are generally represented by the formula

OK

uH

can be characterized in the X chlorine or 3rom means.

The diazonium salts used in the manufacture of photosensitive Diasonium materials of the invention are used include those known in the literature Diazonium salts, usually in the form of their double salts with zinc chloride, stannous chloride, .Bordifluorid and - the like Compounds are used according to the invention

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suitable connections are:

(1) p-Diethylaminobenzenediazonium fluoroborate

(2) p-Amino-N-ethyl-ortho-toluidine deazonium fluoroborate

(3) p-Amino-N-ethyl-N-hydroxyethylanilinediazonium fluoroborate

(4) 4-p-Morpholinylanilinediazonium fluoroborate

(5) p-Amino-N-cyclohexyl-N-ethylanilindiazoniuinhydrogentetrachlorozincate

(6) 4- (4-Methy1-1-piperaziny1) -anilindiazonium hydrogen tetrachlorine tin cat

(7) 2,5-Diethoxy-4- (4-methyl-1-piperaziny1) -anilinediazonium fluoroborate

(8) 1- (2,5-Diethoxy-4-aminophenyl) -4-ethoxycarbonyl-lpiperazine diazonium fluoroborate

(9) 2,5-Biethoxy-4 (4-butyl-1-piperazinyl) aniline-azonium hydrogentetrachlorozincate

(10) 2,5-diethoxy-4- (4-methyl-1-piperazinyl) -benzenediazoniumhyd roe tetrachlorocinicate

(11) 2,5-dibutoxy-4- (4-methyl-1-piperazinyl) -benzenediazonium aide-drug tetrachlorocinlcat

(12) 2,5-dirnethoxy-4- (4-ethyl-1-piperazinyl) -benzenediazoniumhyd rogent e trachlorozincate

(13) 2, i> -I) ipropoxy-4 (4-ethyl-1-piperazinyl) -benzenediazonium hydrogen tetrachlorozincate

(14) 2,5-Diethoxy-4- (4-butyl-1-piperazinyl) -benzenediazonium hydrogen tetrachlorozincate

(15) 2,5-Dipropoxy-4- (4-butyl-1-piperaziny1) -benzenediazonium hydrogen tetrachlorozincate

(16) 4- (4-iiethyl-1-piperazinyl) -benzoläiazoniumhydrogentβtrachlorzincat

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. (17) 4- (4-Ethyl-1-piperazinyl) benzene diazonium hydrogen tetrachlorozincate

(18). 4- (4 - Fb.enyl-l-piperazinyl) -benzenediazoQiumhydrogan-

tetrachlorozincate

(.19) 2,5-D.iphenoxy-4 - ("4 ~ me-thy 1-1-pipäraziiay 1) -benzoldiazonxum-

hydrogen tetrachlorozincate

(20) 2,5-di- (p-methy! Phenoxy) -4 ^ (4-ethy1-1-piperazinyl) -

benzenediazonium hydrogen tetraclalorzincate

(21) 2,5-diethoxy-4 - (. 4- (2-hydroxyethyl) -pipe-razinyl) -

benzene diazonium hydrogeatetrachlorocate

(22) p- (4- (2-Hyäroxyäthyl) -l-piperazittyl) -bensoläiazonium- * hydrogen tetrachlorite

(23) 2,5-Dimethoxy-4 - ("4-methyl-1-piperazinyl) -benzenediazonium-

hydrogentetraohlorsinkat

(24) -3-Butoxy-4- (4-methyl-l.-piperazinyl) -beazoldiazonium hydrogen tetrachlorozincate

(25) 4- (4- (3 ~ Hydroxypropyl) -l-piparazinyl) ~ Benzoldiazonium-Hydrogentetrachlorzincat

(26) 2,5 ~ dietoxy-4- (4-ptienyl-1-pip8razIn.yl) -denzOldiazoniunihydrogentetrachlorzincat

(27) 2,5-diethoxy-4- (4-ethoxy oar bony l-l-p.ipera.zinyl) ^ -benzenediazonium hydrogen tetraciilorzincate

(28) 2,5-DibutQxy-4- (4-ethoxy carbony. 1-1-piperazinyl) -benzene-diazonium hydrogen tetrachlorozincate.

The diazotype light-sensitive materials are made according to the techniques known from the literature. Thus, the diazo type coating layer can contain 0.5 to 5.0 parts of the selected diazo compound per 100 parts of lacquer solution

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keep.

The lacquer solution can also contain various additives customary for the production of light-sensitive diazotype materials. These are metal salts which intensify the color image, such as ammonium sulphate, nickel sulphate, zinc chloride and the like; Stabilizers, such as thiourea, thiourea Ally ₅ naphthalenetrisulphonic and similar compounds!; Acids that retard pre-coupling such as acetic acid, boric acid, tartaric acid, etc .; hygroscopic agents such as glycol, glycerin and like compounds; Wetting agents such as saponin, lauryl sulfonate, cetylbenzenesulfonate, oleic acid amides of N-methyl taurine and similar compounds.

The base on which the lacquer solution is applied can be any base that is in the diazotype field is used. Examples of this base are all types of high quality sulfite cellulose paper, rayon or Cotton fabrics, starch-filled fabrics, in particular hydrolyzed cellulose acetate films, regenerated Cellulose acetate and the like.

The following examples illustrate the practice of the invention; the specified parts are parts by weight, unless otherwise stated.

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iwenge in D. Gram 5 '.O- 2 4th , 0 100 , 0

Example 1;

A paper oasis material is mixed with a solution of the coated with the following composition:

Composition of the solution

citric acid

Zinc chloride

2-chlororesorcinol -

p- (Ethyl (2- hydroxyethyl) amino "] benzene iaz oniumc hlorzinlca t

Silica pigment (Cab-o-Sil) water

The paper was dried and the photosensitive was removed Material was placed under a clear original in the usual manner known for aazotype photographic printing exposed to light. The development of the picture was over this causes the exposed paper to be exposed to the ammonia vapor suspends. According to the original, a red-brown one became Color image was formed which had a high contrast density. The color density and redness of the produced color image showed that the dye had high coloring power.

Example 2: '

A suitable base material is made with a solution as follows Composition coated:

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BATHROOM OB5ÜINAL

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Ethylene Glycol Citric Acid Zinc Chloride 2-Chlororesorcinol

p-Morpholinobenzene diazonium chlorozincate Silica water

Parts by weight "3 5 5 2.

3 2

1Ü0

The base material was dried and exposed to light under a transparent original. After that the " exposed paper exposed to ammonia vapor. A deep red orange dye was obtained, which has a much possessed stronger visibly perceptible density compared to those dyes in which in the above-mentioned composition Resorcinol or a 2-alky! Resorcinol instead of 2-chlororesorcinol was used. The improvement of, Color density. is especially less with the very important ones strong pencil lines noticeable.

example J>:

A suitable base material is covered with the composition of the following composition:

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Parts by weight

Ethylene glycol 5

Citric acid 5

Tin chloride 5

2-chlororesorcinol 2

5-methyl-4-pyrrolidinylbenzene,

diazonium chlorozincate

Silica 2

V / ater 100

The base material was dried and exposed to light under a transparent original. The exposed paper was developed over ammonia vapor. A deep red-orange dye was obtained ₉ which showed much more visibly discernible dicates than dyes obtained using resorcinol or a 2-alkylresorcinol _β instead of 2-chlororesorcinol. The improvement in the density of the ink is particularly noticeable in the very important, less vigorous pencil strokes.

example Ai

Mn suitable base material was made with a solution as follows Composition coated:

Parts by weight

Ethylene glycol ~. 3

Thiourea 4

Citric acid 5

Zinc chloride 5

2-bromoresorcinol 009830/1429 ²

p-Cethyl (2-hydroxyethyl) amino ~] -

benzold iazonium chlorozincate 4

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Parts by weight

Silica 2

Water 100

The base material was dried and placed under a translucent Original exposed to light. The exposed kapier was then developed using ammonia vapor. JJs became a deep red-brown dye is obtained, the much larger one visually perceptible density oesass as dyes made using resorcinol or a 2-alkylresorcinol instead of 2-bromoresorcinol in the above composition were obtained. The improvement of the density of parquet is especially useful for the very important, less vigorous pencil strokes noticeable.

By comparative tests with the above-mentioned materials and other coupling components such as 2-methylresorcinol and 4-chlororesorcinol have been shown to be the 2-halo resorcinols of the present invention compared to other coupling components with improved color images Give color density and red tint.

Claims;

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Claims (3)

1.) Photosensitive diazotype hatorials, which after the exposure and the action of ammonia give a color image of high contrast density and high pulp strength, marked through a base layer that is coated with a photosensitive composition that is a light-sensitive diazonium salt and 2-chlororesorcinol or ■ Contains 2-Lromresorcin al3 coupling component. 2.) Diazotype r.material according to claim 1, characterized in that that the coupling component is 2-chlorresorcinol, 3.) diazotype material according to claim 1, characterized in, that the coupling component is 2-bromoresorcinol. 0 0 983 0/1429 b «, oRIGiNAL