DD263982A1 - PROCESS FOR PREPARING 2-DIAZO-1-OXO-1,2-DIHYDRO-NAPHTHALENE DERIVATIVES - Google Patents

Abstract

The invention relates to a process for the preparation of 2-diazo-1-oxo-1,2-dihydronaphthalenderender, which find application in image recording. The aim of the invention is to provide a process for the preparation of novel compounds with increased photosensitivity. This is achieved according to the invention by the introduction of hydroxy or alkoxy groups in the 7-position of 2-diazo-1-oxo-1,2-dihydronaphthalene.

Description

2. The method according to claim 1, characterized in that R ₂ and / or R ₃ sulfonic acid ester of aromatic polyhydroxy compounds.

Field of application of the invention

The invention relates to a process for the preparation of novel 2-diazo-1-oxo-1,2-dihydronaphthalenderender which is used in image recording application.

Characteristic of the known state of the art

2-Diazo-1-oxo-1,2-dihydronaphthalene derivatives are disclosed in various imaging materials such as photoresists, printing plates, diazo copying disks, and the like. a. used since lanpem. The properties of the 2-diazo-1-oxo-1,2-dihydronaphthalengrundkörpers can be controlled by substitution within certain limits. Above all, the 4- or 5-membered sulfonated derivatives and the sulfonic acid esters or amides derived therefrom are known, as described in J. Koser: Light-Sensitive Systems, New York 1965. These modifications can affect various application properties interesting properties. Thus, one can produce positive or negative-working photosensitive layers via suitable esters or amide components. Furthermore, the solubility and compatibility with various binders can be controlled in this way.

Also known is the introduction of nitro groups into the 2-diazo-1-oxo-1,2-dihydronaphyllene base.

All these modifications have little effect on the absorption spectrum in the long-wavelength range around 400 to 405 nm. In particular, it is not possible to further shift the absorption in the long-wave range and thus to contribute to increasing the photosensitivity.

Object of the invention

The object of the invention is to provide a process for the preparation of novel 2-diazo-1-oxo-1,2-dihydronaphthalene compounds having increased photosensitivity.

Explanation of the essence of the invention

The invention has for its object to provide a process for the preparation of novel 2-diazo-1-oxo-1,2-dihydronaphthalene whose light absorption is extended in the long wavelength range to specify. According to the invention, this object is achieved by introduction of hydroxy or alkoxy groups in the 7-position of the 2-diazo-1-oxo-1,2-dihydronaphthaler. IViaπ is based on 1,7-Dihydroxynaphthalenderivaten, which are coupled in an aqueous-alkaline solution or suspension or in a solvent mixture with Arendiazoniumsalzen in the 2-position. if the

Coupling is not specifically in the 2-position, can also nltrosiert v / earth. The resulting K'jpplungsprodukte or oxime derivatives are reduced to the amino compounds and then reacted with nitrite to the 1-diazo-1-oxo-1,2-dihydro-7-hydroxynaphthalenen invention. The hydroxy group in the 7-position can subsequently be alkylated. Preferably, an alkyl radical having a chain length of from one to eight carbon atoms is introduced for this purpose. The compounds of the invention are characterized in that the light absorption of the boring absorption band, the boi previously known derivatives of the same body is 400 to 405nm, is advanced significantly baihochrom to 430 to 440 mn.

This achieves a better adaptation to the emission of the exposure devices. In particular, when mercury vapor lamps are used, a better utilization of the emission wavelength of these radiators located at 436 .mu.m is achieved. In practical use, this translates into a higher photosensitivity. This circumstance has a particularly advantageous effect on exposure apparatus operating monochromatically with light of wavelength 436 nm. Depending on the choice of the other substituents, it is possible to prepare derivatives of the compounds according to the invention which are soluble in both aqueous and organic media.

embodiments

10 g of 1,7-dihydroxynaphthalene are dissolved in 150 ml of water and mixed with 4.2 g of sodium nitrite dissolved in 50 ml of water. The solution is cooled to ⁰ ° C. and slowly acidified with acetic acid. After 3 hours, the mixture is concentrated to about 50 ml water jet vacuum and the solid is filtered off with suction. This gives 6.5 g of 7-hydroxy-1,2-naphthoquinone-2-oxime (Vf .. .. "tion 1).

8 g of the compound 1 are dissolved in 100 ml of 2.5 N sodium hydroxide solution and treated at room temperature in portions with about 28 g of sodium dithionite so that the temperature rises to 70 ° C. It is acidified with hydrochloric acid and filtered off with suction, the solid is recrystallised from hydrochloric acid. 5.3 g of 1,7-dihydroxy-2-aminonaphthalene hydrochloride (Compound 2).

2 g of compound 2 are dissolved in a mixture of 20 ml of ethanol and 10 ml of water, cooled to ⁰ ° C. and treated dropwise with 0.65 g of sodium nitrite dissolved in a little water. Then acidify carefully with dilute hydrochloric acid.

After 15 minutes, 20 ml of water are added and the solid is filtered off with suction. Yield: 1.12 g of 7-hydroxy-1-oxo-2-di8zo-1,2-dihydronaphthalene (Compound 3).

Example 2:

2.2 g of aniline are mixed with 8, brine hydrochloric acid (dilution 1: 1) and diazotized at ⁰ ° C. with 1.44 g of sodium nitrite. The diazonium salt is added dropwise at 8-10 ° C in a solution of 5 g of 1 J-dihydroxynaphthalene-sulfonic acid and 3.2 g of anhydrous sodium carbonate in 50 ml of water. It is allowed to stand at room temperature for 30 minutes. Thereafter, the mixture is heated to 60-70 ⁰ C and spatially spiked with about 10g sodium dithionite until the solution has turned pale yellow. Allow to cool and acidify carefully with concentrated hydrochloric acid. This precipitates the 1 ^ -Dihydroxy ^ -sulfo ^ -aminonaphthalenhydrcchlorid (compound 4); Yield: 3.2g.

2 g of compound 4 are slurried in 15 ml of water and cautiously at 0 ⁹ C with stirring with a mixture of 1.5 g of copper sulfate pentahydrate and 0.52 g of sodium nitrite, dissolved in 8 ml of water. After standing at ⁰ ° C. for 15 minutes, the 4-sulfo-7-hydroxy-2-diazo-1-oxo-1,2-dihydronaphthalene (compound 5) is filtered off with suction; Yield: 1.2g.

Example 3:

2.5 g Vorbindung 3 are mixed with 5 ml of dimethyl sulfate and heated to 40 ° C for 2 hours on a water bath. The solid first goes into solution, while the end of the reaction solidifies the contents of the flask. The reaction product: 7-Meihoxy-1-oxo-2-diazo-1,2-dihydronaphthalene (Compound 6) is isolated by suction.

Claims (1)

-1- 263 9d2 Claims: 1. A process for the preparation of 1-diazo- ^1- oxo-1,2-dihydronaphfbalenderivaten, characterized in that naphthalene derivatives of general formula 1, in which R _{1 is} hydrogen, alkyl having 1 to 8 carbon atoms, R ₂ and R _{3 are} hydrogen, halogen or sulfone groups, coupled with arendiazonium salts or nitronieri and the erhaienen Naphthalenderivate reduced to the corresponding 2-amino-naphthalenes and then with nitrite to the 2 Diazo-1-oxo-1,2-dihydronaphthalene derivatives of the formula 2 in which R ₁ , R ₂ , R _{3 have the} above meaning diazotized.