DD206006A1 - RADIATION SENSITIVE MATERIAL - Google Patents

Abstract

THE TASK ON RADIATION SENSITIVE MATERIAL FOR OPTICAL RECORDING ON THE BASIS OF A PERHALOGENIDSYSTEMS WITH LIGHT to be synthesized DYE PRECURSORS USED IN THE IMAGE CONSTRUCTION RESPONSE STABLE DYES WITH ABSORPTION MAXIMA ON 550nm DELIVER, IS SOLVED BY THE STAHLUNGSEMPFINDLICHE MATERIAL COMPRISING DYE PRECURSORS, PERHALOGENIDEN, BINDERS AND POSSIBLY OTHER PHOTOGRAPHIC ADDITIVENESS AS A COLORING PREPARATION AZOFFINS OF GENERAL FORMULES I AND II IN WHICH, IN THE XS, -CH = CH-; R1, R2 HYDROGEN, ALKYL, CYANETHYL, ALKYLESTER; R3, R4 HYDROGEN, ALKYL, ALKOXY, HALOGEN, -N / R1 / R2; R5 HYDROGEN, HALOGEN, ALKYL, ALKOXY, HALOGENALKOXY, NITRO, CYANO, RHODANO, PHENYL, ARYL, -N / R1 / R2; HALOGEN METHYLSULFINYL, MEANS, INCLUDES.

Description

Radiation-sensitive material

Field of application of the invention

The invention relates to a radiation-sensitive material for direct optical recording.

Characteristic of known technical solutions

Strahlungsespfindliche materials based on Per "halides and dye precursors are already the subject of numerous patents and publications (R, H. Spraqua, HL Fichter / E. Wainer Phot" Sei.Eng, 5, 99 (1961), A.MacLachlan Ö. Phys. Ctem, 71, 718 (1967), RA Fotland Phot.Sei.Eng. 18, 33 (1970), RH Spraque, HL Fichter Phot.Sei.Eng. 8, 95 (1964) RH Spraque, about Urbancik, G. Stewart, Phot, Vol., 9, 133 (1965), RH Spraque, 3. Roscow Phot.Sei.Eng.8, 91 (1964), OS 2 241 563, OS 2 055 872, OS 2,112,836). The dyestuff precursors used here are spiropyranes, arylamines, leuco bases of di- or triphenylraethane dyes, styryl and cyanine bases, as well as indoles, which can only be prepared by elaborate complicated and costly syntheses.They are unstable and desirably defected when exposed to light and heat They also use phenylazonaphthalene, aminoazobenzenes, azo dyes from CH-acidic couplers as image-dye-forming compounds compared to the herköramlichen dye precursors the advantage of a more straightforward

Λ Λ »Π

n ιΛ / ΛΛ .. Γ. K Π ft K

242 6 55 7

Synthesis, a wide variety of possible shades and a higher light fastness. The disadvantage is that during normal processing (exposure, fixation), the longest-lasting absorption of these dyes takes place only up to about 550 nm.

Object of the invention

The aim of the invention is to improve the performance characteristics of silver-free recording materials.

Presentation of the essence is invention

The known optical recording materials generally have the disadvantage that the resulting image dyes are unstable to light and heat, are expensive to manufacture. their absorption maxima are below 570 nm. It is therefore an object of the invention to provide dye precursors for Perhalogenidsysterae that are easy to prepare and as a result of the image formation reaction stable image dyes with Absorptionsraaxima over 550 nra provide »Erfindungsgesnäß the object is achieved by the radiation-sensitive silver-free material consisting of dye precursors, perhalides, binders and optionally further photographic additives, as dye precursors azo dyes of the general formula

H ²

\ -nn- / Vn "" ¹

I ^K 2

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in the X R ₁ . , R ₂ ^R 3 ' • ^R 4

S, -CH = CH-.)

identical or different, hydrogen, alkyl of up to 6 carbon atoms, optionally substituted cyanoethyl, alkyl ester;

same or different. Hydrogen, alkyl with

1 to 6 carbon atoms, alkoxy of 1 to 6

R is carbon atoms, halogen, N ^ 1;

Hydrogen, alkyl of 1 to 6 carbon atoms, optionally substituted, alkoxy of 1 to 7 carbonators, haloalkoxy of 1 to 6 carbon atoms, nitro, cyano, rhodano

Halogen, phenyl, aryl, N 1, haloethyl

^R 2 is sulfinyl, haloethylsulfonyl;

mean, contains «

The azo dyes are prepared by diazotization of the heterocyclic amines and coupling with differently substituted affinobenzenes. «

The perhalides used are preferably Tetrabrorakohlen material, iodofor®, Hexabromaceton and tribroethanol individually or in a mixture. To increase the sensitivity, it is additionally possible to contain UV sensitizers. Common compounds include Michler's ketone, pN, N-diraethylafliinobenzaldehyde and phenthiazine. In addition, additives such as plasticizers (Diaethylformamid) can be used.

The azo dyes, in concentrations of 0.015 raol / 1 to 0.03 raol / l, together with the photosensitive compound, the additives and a binder, are applied to the usual photographic supports, e.g. Polymer film, paper, glass applied. Suitable binders are polymers, polymer mixtures and copolymers.

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Preferably, polystyrene oil is used. The thickness of the recording layer is variable, but is preferably below 10.

The processing of the material is as follows. As a first step, the exposure is carried out with a high-pressure mercury vapor lamp. Their duration depends on the sensitivity of the layer, which is determined by the azo dyes used and the additives. It averages 15 - 120 sec.

The exposure decomposes the perhalide and produces hydrohalic acid. This causes a change in the color of the azo dye at the exposed areas and thus the appearance of the image. · The image embossing is completed with the exposure *

In the second step, the image must be fixed. In this case, both the unreacted perhalide and the unreacted azo dye are removed from the layer by suitable solvents. In polystyrene systems, a mixture of gasoline / acetone / ethyl acetate »has proven itself. The result is blue images on a colorless background. The advantage over conventional perhalide materials lies in the long-wavelength absorption of the dyes and in a high stability of the finished recording against light and heat.

AusfÖhrungsbeispiele example 1

A photosensitive material is prepared by applying the following composition to a polyethylene terephthalate support:

70 rag

100 rag phenthiazine 100 mg ^CH ^ 3 200 mg CBr ₄

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100 rags of dimethylformamide

10 ml polystyrene / methylene chloride / dichloroethane solution (7.5 % ± g)

The layer is dried at room temperature for 10 minutes and then has a layer thickness of 5-8 / Uta. For exposure, a high-pressure mercury vapor HBO 200 is used (removal of sample - lamp 20 cm).

After 120 sec. Exposure to an optical density of 1.0 (573 no, 610 nm).

Example 2

As indicated in Example 1, the following material is prepared and tested:

CH, 0

70 mg

100 mg of phenthiazine · 100 mg of CHI ₃ 200 mg of C8r ₄ 100 rag of diethylformamide

10 ml polystyrene / methylene chloride / dichloroethane solution (7.5 % ± g)

After 60 seconds of exposure the optical density is 1.4 (585 n®, 663 na).

Example 3

A material of the following composition is prepared according to Example 1

το. «g

SCN

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100 mg of phenthiazine 100 mg CHI ₃ 200 mg CBr.

100 mg of dimethylformamide

10 ml polystyrene / methylene chloride / dichloroethane solution (7.5%)

The optical density after 60 sec exposure is 0.5 (5.88 nm, 618 nm).

Example 4

According to Example 1, the following photosensitive material is prepared and processed:

100 mg of phenthiazine 2

CHl 100 mg ₃₂₀₀ mg CB r.

100 mg of dimethylformamide

10 ml polystyrene / methylene chloride / dichloroethane solution (7.5%)

The optical density is after 90 sec exposure 1.2 (565 nm, 623 nm sch).

Example 5

Analogously to the preceding examples, the preparation and processing of the following composition takes place

H. 70 mg

CH.

2426 5 5

100 mg phenthiazine 100 rd CHI ₃ 200 rag ^C8r 4 100 mg dimethylformamide

10 ml polystyrene / methylene chloride / dichloroethane solution (7.5%)

After 60 seconds of exposure, the optical density is 1.15 (580 nm, 625 nm).

Example 6

The following photosensitive material is produced and tested as already stated

^C 2 ^H 5

70 ng

100 rag of phenthiazine 100 rag CHI ₃ 200 ag ^CBr 4 100 rag dimethylformamide

10 ml polystyrene / methylene chloride / dichloroethane solution (7.5 % ± g)

After 30 seconds of exposure, an optical density of 1.6 is reached (570 nm, 624 nm sch),

Example 7

As is known, the following material is produced. The processing corresponds to the previous examples:

70 mg. N

LJ

" ^C 2 ^H 5 100 ag phenthiazine

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200 mg 100 ing

CBr ^ CHI.

100 mg of dimethylformamide

10 ml polystyrene / methylene chloride / dichloroethane solution (7.5 % ± g)

Mach 90 sec exposure is the optical density achieved:> 1, 4 (570 nm, 613 nra)

In Table 1, dyes are compiled, which can also be used according to Example 1.

Table 1:

\ -N (CH ₃ ) ₂

X before exposure 526 549 (mn) after exposure - 416 512 558 O- - 487 510 590 - 426 509 591 I N (CH ₃ ) J 541 518 665 I NH ₂ 527 641 OCH ₃ SOCF, j 538 610 I CH ₃ NO ₂ 550 600 years H 599! OCF ₃ SO ₂ CF ₃ 598! CF ₃ 588 i 588 j 586 I 582

Claims (1)

invention claim R in the R ₁ * R ₂ ' ^R S, -CH = CH-; identical or different, hydrogen, alkyl of 1 to 6 carbon atoms, optionally substituted, cyanoethyl, alkyl esters; identical or different, hydrogen, alkyl sit 1 to 6 carbon atoms, alkoxy slit I to 6 carbon atoms »halogen
R ¹ z Hydrogen, halogen, alkyl of 1 to 6 carbon atoms, optionally substituted, alkoxy of 1 to 6 carbon atoms, haloalkoxy of 1 to 6 carbon atoms, nitro, cyano »Rhodano, Phenyl, aryl, N-haloethylsulfinyl, halo-ene