DD154403A1 - ONE OR TWO-COMPONENT DIAZOTYPE MATERIAL - Google Patents

Abstract

The invention relates to a one- or Zweikomponentendiazotypiematerial with significantly improved light stability. This is achieved by adding Cu (II) salts of organic carboxylic acids as bleach inhibitor to the diazo system. These copper salts are easy to synthesize and in no way affect the sensitometric properties.

Description

VEB Filmfabrik Wolfen Wolfen, 17. 11. 1980

PN 856 Wa / Hm

DC. Werndl Int.Cl. ³ / G 03 C 1/60

Dr. Marx

Dr. Rehorek

Dr. Epperlein

2 2 6 1 2 3 -ι-

One- or two-component diazo material

Application of the invention

The invention relates to a diazotype material with improved

Light stability of the image dyes.

9. ^. R. ^, L ^e .r., F? ΐ ^ Κ ^ ^e , L k ^e H i ^ai ? i ^{n s} M h tec African solutions The image dyes of diazotype materials are subjected by the radiation at the reader and by cloning tasks of diazo to diazo a considerable burden. Therefore, in addition to maintaining all other essential properties such as sensitivity, resolving power, coupling activity and duplicating ability, the light stability of the image dyes is an essential parameter of powerful diazo systems.

It is possible to a limited extent, by suitable substitution of diazonium and / or coupler component to improve the fading resistance of the azo dyes formed. However, the efficiency is low with relatively high synthesis effort.

It has therefore been found to be more advantageous to add certain compounds to the diazo system which suppress the fading under the conditions of the reading and exposure apparatuses. These fading inhibitors must fulfill several secondary conditions, such as system compatibility, suitable absorption maximum (as short-wavelength absorbing as the diazo component), stability in the processing process and good

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Accessibility. So far, hindered phenols (DE-PS 1 772 981), ethylene diamines (DE-AS 1 797 322) and 3-anilinopyrazoles (DD-VVP G 03 c / 221 629) were used as additives. The disadvantage of these compounds is the relatively low effect and partly in the high synthesis effort, which is necessary for the representation of the substances. Phosphoric acid anilides (DD-WP G 03 c / 222 062) can be relatively easily produced, but worsen the duplicability. All the compounds described so far are inherent in that they only maintain the stability of light for a time until they themselves are destroyed.

Object of the invention

The aim of the invention is to substantially improve the light stability of diazo materials.

Explanation of the essence of the invention

The compounds hitherto used for increasing the light stability have the disadvantage that they are too low in their effect over a longer period of time.

It is the object of the invention to find additives to Diazotypiematerial that stabilize the image dyes so that no or only slight fading effects occur even when exposed to light of several hours. All other properties of the material should be retained. The object is achieved erf indungsgem.äß characterized in that the one- or Zweikomponentendiazotypiematerial with fading inhibitor contains one or more Cu (II) salts of organic carboxylic acids.

Cu (II) salts of organic carboxylic acids, e.g. unbranched saturated aliphatic monocarboxylic acids (capric acid), branched saturated aliphatic (methyl-ethylacetic acid), unbranched unsaturated aliphatic (propiolic acid), branched unsaturated aliphatic (methacrylic acid) aromatic (salicylic acid), araliphatic (mandelic acid),

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cyclic aliphatic (cyclohexane carboxylic acid), heterocyclic (isonicotinic acid), saturated aliphatic dicarboxylic acids (adipic acid) unsaturated aliphatic (Maleinr ¹ acid), aromatic (phthalic acid), hydroxycarboxylic acids (lactic acid), halogen carboxylic acids (oij / 3-dichloro-propionic acid), keto acids (pyruvic acid) and tricarboxylic acids (citric acid). The Cu (II) salts are readily accessible synthetically (Gmelin's Handbook of Inorganic Chemistry, Vol. Cu) and, when used as inhibitors, lead to a considerable increase in the light fastness of the diazo materials. They show good system compatibility, so that all other requirements for a diazo system such as duplicability, thermal stability and sensitivity are fully met.

The copper salts are mixed to form a Diazotypiegießlösung with a diazonium salt, a stabilizer acid and optionally with one or more couplers and then dissolved in a polymer solution. This casting solution is then applied to a support. Suitable diazonium salts include 2-Aminobenzendiazonium-, 4-Aminobenzendiazonium-, 4-Thiobenzendiazoniumsalze and phenylenediamines. Suitable couplers are any known containing a hydroxy group in the o-position, e.g. 2-hydroxy-3-naphthamides, 2,3-dihydroxynaphthalenes, resorcinol or β-naphthol. As binders, cellulose derivatives, vinyl polymers, copolymers of vinyl chloride and vinyl acetate, polystyrenes, mixed polymers of alkyl acrylates and acrylic acid, polyethylene oxides are usable. Furthermore, the material may still contain the usual additives such as stabilizer acid, development accelerator and plasticizer. Support materials for the photosensitive layer may include polymer films of e.g. Polyethylene terephthalate, cellulose triacetate, paper, translucent paper, glass and metal.

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Failure to use

In 1000 ml of a 10% cellulose acetate solution becomes

-2 -2

Diazosystern of 4.5 ♦ 10 moles of diazonium salt, 5.3 · 10th

mol of coupler, 1.7 x 10 -5 mole of p-toluenesulfonic acid and 10 to 10 ~ mol of Cu (II) salts of an organic carboxylic acid. This is cast on 10 - 15 m ^ Polyethylentherephthalatunterlage to obtain a transparent film. The image dye is generated by developing in basic medium and subjected to xenotest for 15 hours. The results are shown in the table. As diazonium salts were used:

(I) 2,5-Diethoxy-4-morpholinobenzene diazonium tetrachloroborate

(Π) 2,5-dibutoxy-4-morpholino-benzene-diazonium tetrachlorozincate

as a coupler

(1) 2-hydroxy-3-naphthoic acid o-anisidide

(2) 2-Hydroxy-3-naphthoic acid ~ ^ "2,4-dimethoxy = 5-chloroanilide_7

(3) 2-Hydroxy-3-naphthoic acid ^ ~ 2-methyl-4-chloro-aryl_7

(4) 2-Hydroxy-3-naphthoic acid ^ ~ 2-methyl-4-methoxyanilide_7

(5) 2-hydroxy-3-naphthoic acid - ^ "* 2-methyl-3-nitroanilide_7

(6) resorcinol

(7) β-naphthol

characteristics used substance amount diazonium pimp fading rate without the carboxylic acid Surname component- 15 h Xenotest inhibitor th with inhibitor Monocarboxylic acid 2.36. 10 ' ² mol aliphatic. Cu (II) propionate 2,13. 10 ~ ² mol I (L) / (6) 0 % 24 % saturated. 3.55 · 10 " ² _m0 l II (1) 5% 51 % unbranched 4.73 x 10 "nol II (6) 0 % 29 % C ₁ - C ₁₂ 9.47 · 10 ^-2 mol II (7) 0 % 90 % 2.13 x 10 ^"2 mol II (5) 8 % 50 % 2.13 x 10 -8 x ² mol II (2) 3 % 51 % 2.09 x 10 ^"2 mol II (3) 14 % 49 % butyrate Cu (II) 1.72 x 10 ^"2 mol I (I) / (6) 0 % 24 % Cu (II) -capronat 1.72. 10 ~ ² mol II (1) 0% 51 % 1.72 x 10 ^"2 mol II (6) ο % 26 % 2.73 x 10 ^"2 mol II (5) 15 % 43 % Cu (II) acetate 2.21 "10" ² mol I (L) / (6) 2 % 42 % laurate, Cu (II) II (1) 10 % 47 %

Characteristic of the carboxylic acid used name θ substance amount 3-azonium components pimp Fade rate with inhibitor 15 h Xenotest without inhibitor Monocarboxylic acid aliphatic, saturated, branched ^C 4 - ^C 10 Cu (II) -pivalinat 3.77 x 10 ^"2 mole 2.26 x lO ~ ² mol 1.50 x 10" ² rnol 2.26 x 10 * ^"2 mol 1.50 x 10" ² moles of 2.26 x 10 ^-2 mol HHHHHH HHHHH (l) / (6) (1) (7) (2) (3) (4) 3% 0 % 0 % 0 % 0 % 9 % 27 % 51 % 30 % 50% 39 % 34 % Monocarboxylic acid aliphatic, unsaturated, unbranched Cu (II) oleate 1.90 · lO ^"2 mol 1.90 mol 1.90 .LO ~ ² x 10" ² πιο1 II II II (1) (6) (3) , 8% 0 % 8% 51 % 26 % 39 % Monocarboxylic acid aromatic Cu (II) benzoate 6.55 × 10 ^-3 πιο1 II (1) 11% 51% Monocarboxylic acid araliphatic Cu (II) phenyl acetate 9.00 x 10 ^-3 inol 1.50 .10 " ² mol I II (1) / (6) (7) 5 % 0 % 24 % 90%

Characteristic of the carboxylic acid used ί name Substance amount Diazonium components pimp Bleaching advice without inhibitor e 15 h Xenotest with inhibitor Monocarboxylic acid aliphatic, halogen-substituted Cu (II) -chloracetat 3.01 · lO ~ ² mol II (1) 8 % 47 % Dicarboxylic acid aliphatic, saturated Cu (II) malonate 1.24 · 10 ^-2 mol II (1) 17 % 51 % Dicarboxylic acid * aliphatic, unsaturated Cu (II) maleate 1.35 · 10 " ² πιο1 II (1) 19 % 51 % Aromatic dicarboxylic acid Cu (II) phthalate 1.20 "10" ² mol II (1) 17 % 51% tricarboxylic citrate Cu (II) 1.25 .10 " ² mol II (1) 20 Y ₀ 51 % keto acid Cu (II) pyruvate 1.50 x 10 ~ ² ΐηο1 II (1) 20 %. 51 % hydroxy Cu (II) -laktate 1,81 .10 "" ^ mOl II (1) 13 % 51 % Straight carboxylic acid Cu (II) -isonicotat 1.23 x 10 "" ² ιηο1 II (1) 18% 51 %

Claims (4)

invention claim 1. One- or Zweikomponentendiazotypiematerial with fading inhibitors characterized in that it contains as fading inhibitor one or more Cu (II) -Sslze organic carboxylic acids. 2. One- or Zweikomponentendiazotypiematerial with fading inhibitors according to item 1, characterized in that it contains as fading inhibitor one or more Cu (II) salts of organic monocarboxylic acids. 3. One- or Zweikomponentendiazotypiematerial with fading 'inhibitors according to item 1, characterized in that it contains as fading inhibitor one or more Cu (II) salts of organic dicarboxylic acids. 4. A one- or two-component diazotype material with bleaching inhibitors according to item I, characterized in that it contains as bleaching inhibitor one or more Cu (II) salts of organic tricarboxylic acids.