DD148910A3 - ONE OR TWO-COMPONENT DIAZOTYPE MATERIAL - Google Patents

Abstract

The invention relates to a diazotype material with novel photosensitive compounds, which may be one- or two-component material. Through the use of diazonium compounds, which are decomposed by light of the wavelengths of 500 to 600 nm, a photosensitive diazotype material is to be created for the range of visible light of 500 to 600 nm. This object is achieved by the use of a- (phenyldiazonium-4) -4-dialkylaminocinnamic acid derivatives. The thus prepared Diazotypiemeterialien allow for the first time a duplication of red templates or information that Bildbildly of substances that absorb in the range of visible light, preferably from 500 to 600nm, are constructed.

Description

VEB Filmfabrik Wolfen Wolfen, 9.4.1979

PN 753

21 3 28 2 - ^

Int. Class .: G 03 c 1/54 single- or two-component diazotype material

Field of application of the invention .;

The invention relates to a diazotype material with novel photosensitive compounds, which may be one- or two-component material.

Charac k de r b ekannten, technical ^ Lösun gen is known, the diazo based on the ability of aromatic diazonium with color coupling substances azo dyes su produce and lose photochemically sfähiskeit by Lichteinwirkuns their Kupplun ^. The latent image obtained by exposure is then developed by the action of ammonia gas, by alkaline baths, or thermally by base-releasing additives. Mainly benzene diazonium salts having a tertiary amino group in the 4-position to the diazonium group and further substituents on the benzene ring, preferably in 2- and 5 ßfrellung used.

The important properties for the diazotype, such as high photosensitivity, sufficient thermal stability and coupling ability of the diazonium compounds are mainly determined by these substituents. The absorption of such benzene diazonium salts substituted by a ternary amino group in the 4-position to the diazonium group is for the maxima of the absorptions on

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the range between 350 and 450 nm limited, it must be exposed to light of the wavelengths in this area. Tertiary amino groups substituted in the 2-position to the diazonium group in the diazonium salts extend the range up to 450 nm at the maximum of the absorption (H. Böttcher et al., J. prakt. Chem. Jjij, 725 (1973)). The maxima of the absorption of diazonium salts of higher condensed aromatics such as ζ.Be pyrene or cyclically linked such. Pluvors reach 480 nm (T. Tsunoda et al., Nippon shashin Gakkai Kaishi 2 ^, 2? (1966)). In US-F. 2,660,526 describe the monodiazotised 4,4'-diamines of biphenyl and stilbene, which absorb even longer wavelengths. The previously described diazonium salts, which are used in the diazotype, thus absorb light up to a maximum of 500 nm. These diazotype materials are sensitive only to exposure to UV or blue light.

, Aim of the invention

 The aim of the invention is to provide a diazotype material which is sufficiently photosensitive to the visible light range, preferably from 500 to 600 nm, and allows the reproduction of information which is image-wise constructed of substances preferably in the range of visible light Absorb 500 to 600 nm.

Presentation of We sens THE INVENTION The object of the invention is to find diazonium compounds that can be decomposed by light of wavelengths of 500 to 600 nm and are formed at the unexposed areas by a basic developing with one or more couplers, colored image dyes may ·

213282

The object is achieved in that as photosensitive and couplable compounds. ^ - (phenyldiazonium-4) -4-dialkylaminozimtsäurederivate the general formula

in the

R _{1 is} hydrogen, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, halogen, preferably fluorine or chlorine, a fluorinated alkoxy group having 1 to 4 carbon atoms, a cyanoalkoxy group having 1 to 4 carbon atoms Atoms, the trifluoromethyl group;

R _{2 is} hydrogen, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, halogen, preferably fluorine and chlorine, a fluorinated alkoxy group having 1 to 4 carbon atoms, a cyanoalkoxy group having 1 to 4 carbon atoms Atoms, a trifluoromethyl group;

R _{3 is} hydrogen or halogen, preferably fluorine or chlorine;

R, R is an alkyl group having 1 to 5 carbon atoms, aralkyl group having 1 to 5 carbon atoms in the alkyl group, or R and R together form a 5- or 6-membered saturated heterocyclic ring consisting of nitrogen, carbon and oxygen atoms ;

Y is a carboxyl group, an ester group - COOR, where Rg can be an alkyl group having 1 to 4 carbon atoms, an acid amide group - CONR ₄ R ₅ , a nitrile group and

- 4- 213282

X is the anion of the diazonium compound

mean to be used in a diazonium material. In addition to the known in diazotype stabilizer acids such. SuIfosalicylsäure. Oxalic acid and the like. For example, couplers such as e.g. Naphthols, phenols, compounds with acidic carbon atoms, etc. The film-forming polymer in which either diazonium salt, stabilizer acid and coupler or only diazonium salt and stabilizer acid are embedded can bind the binders known in diazotype, such as e.g. Cellulose esters, polyvinyl alcohol u.a «be used.

As carrier material can as usual plastic film, paper, transparent paper, transparent paper, glass u.a. be used.

The compounds according to the invention show their maximum extinction in the range from 550 to 590 nm. For the first time, such an exposure with green light and a duplication of red templates is possible.

Exemplary embodiments Example 1

In 1000 cm of a 7.5% cellulose acetate solution in methylene

2 chloride / methanol, which is cast on 10 to 15 m surface and gives a transparent film, the following diazo system is introduced:

10 g of ethyl (phenyldiazonium-4) -4-dimethylaminocinnamic acid with 10 g of 2,3-dihydroxynaphthalene

2 g sulfosalicylic acid

By exposing a black or red original and development by ammonia, the purple diazotype material gives a red-brown image. The UV-visible spectrum of this diazo system shows an absorption maximum at 556 nm (FIG. 1).

- 5 - 2 13 2 8 2

example

In 1000 cm 'of a 7.5% strength ^s cellulose acetate in

Methylene chloride / methanol, which is cast on 10 to 15 m surface and gives a transparent film, the following diazo system is introduced:

10 g of o, - - (phenyldiazonium-4) -morpholinozimtsäure 7 g of β-naphthol 2 g of p-toluenesulfonic acid

By exposing a black or red template and developing with ammonia, the purple diazotype material gives a red image.

Example 3

3 In 1000 cm of a 7.5% solution of cellulose propionate in methylene chloride / methanol, which is cast on a 10 to 15 m surface and gives a transparent film, the following diazo system is introduced: 10 g of 0 <- (phenyldiazonium-4) -4 pyrrolidino ~ 3-methyl

cinnamic acid 4-methyl ester 7 g acetoacetanilide 2 g oxalic acid

By exposing a black or red template and developing with ammonia, the yellowish image of the purple diazo material is obtained.

Example 4

In 1000 cm of a 7.5% cellulose acetate solution in methylene chloride / methanol, which is cast on 10 to 15 m surface and gives a transparent film, the following diazo system is introduced: 10 g of <5 - (phenyldiazonium ~ 4) -4-piperidinozimtsäure -

dimethylamide 4 g naphthol AS-OL

, ₆ . 2 13 2 8 2

2 g of β-naphthol

2 g of acetoacetanilide

2 g of oxalic acid

By exposing a black or red template and developing with ammonia, the purple diazo material gives a brown picture.

example

In 1000 cm of a 6% polyvinyl alcohol solution in water, which is cast on 10 to 15 m surface and gives a transparent film, the following diazo system is introduced:

10 g of (phenyldiazonium-4) -4-dimethylaminocinnamic acid

nitrile 8 g R-salt 2 g sulfosalicylic acid

By exposing a black or red original and developing with ammonia, the purple diazo material gives a red-brown image.

Example 6

The following diazo system is introduced into 1000 cm of a 7.5% cellulose acetate solution in methylene chloride / methanol, which is cast on a 10-15 m surface and gives a transparent film.

10 g of v '- (phenyldiazonium-4) -4-dimethylaminocinnamonitrile 2 g of sulfonylic acid

By exposing a black or red original and developing by dampening at constant. pH ^ 8 with phloroglucinol and 2-hydroxy-3-naphthoic acid ethanolamide gives a brownish picture.

Claims (1)

• - 7 - 2 13282 invention claim One- or two-component diazotype material, characterized in that the photosensitive compound is 06- (phenyldiazonium-4) -4-dialkylaminocinnamic acid derivatives of the general formula -CH = C- in the R. hydrogen, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, halogen, preferably fluorine or chlorine, a fluorinated alkoxy group having 1 to 4 carbon atoms, a cyanoalkoxy group having 1 to 4 carbon atoms Atoms, the trifluoromethyl group; R "'is hydrogen, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, halogen, preferably fluorine and chlorine, a fluorinated alkoxy group having 1 to 4 carbon atoms, a cyanoalkoxy group having 1 to 4 carbon Atoms, a trifluoromethyl group; R. is hydrogen or halogen, preferably fluorine or chlorine; R.) An alkyl group having 1 to 5 carbon atoms, Aralkyl-Rgi group having 1 to 5 carbon atoms, in the alkyl radical or R. and R together form a 5- or 6-membered saturated heterocyclic ring consisting of nitrogen, Carbon and oxygen atoms; 213282 Y is a carboxyl group, an ester group - COOR_, where R_ can be an alkyl group having 1 to 4 carbon atoms, an acid amide group - CONR.R_, a nitrile group and X is the anion of the diazonium compound. For this 1 page drawings