SU1447813A1 - N,n,nъ,nъ-tetra-(2-oxy-6-chloro-3-chloro-3-oxymethylphenylmethyl)-diamide malonic acid as hardener of gelatine emulsion photosensitive layers - Google Patents

Abstract

The invention relates to substituted amides of acids, in particular N, N, N, N-tetra- (2-oxy-6-chloro-3-oxy-methylphenylmethyl) diamide of malonic acid - dubitel emulsion gelatin layers. The purpose of the invention is to generate new, more effective tanning agents of this class. Synthesis of a new substance is carried out from (N, N, N, N.-tetra-3-chlorphenoxymethyl) diamide of malonic acid, isopropyl alcohol and paraform at boiling. Output 72% i p 1,4990, gross-f-la C lLj Cl NjOjo. Tests of a new tanning agent in photographic materials show the best strength of the emulsion layer and the value of the optical density of the veil (P 350 g and DO 0.01) in comparison with the analogue (P 300 g and D. 0.02). 1 tab. g

Description

.Hib

This invention relates to a novel chemical compound, namely, N, N, N, N tetra- (2-hydroxy-6-chloro-3-oxymethylphenylmethyl) diaonic of malonic acid, which can be used as an effective tanning agent of gelatin photosensitive layers. .

The purpose of the invention is to find out in the range of N, N, N, N-tetrasubstituted malonic acid diamides a new tanning agent, which improves the strength properties of emulsion gelatin photosensitive layers.

Example. Place 66.4 g (0.1 mol) of N5N, N jN-tetra-3-chlorophenoxymethyl) diamide of malonic acid and 48 g (0.8 mol) of isopropanol in a four-necked flask j equipped with a stirrer, reflux condenser and thermometer. Then, with constant stirring, 24 g (0.8 mol) of paraform and 27 ml of water are added to the reaction mass. The reaction mass is heated to the boiling point of the solvent (82.4 ° C) and boiled for 6-8 hours until the reactants are completely dissolved. After that, the thermometer is replaced with a 1 Dean-Stark garden and, continuing heating, the azeotrope isopropanol – water under vacuum (40–50 im Hg) is distilled off. The synthesized compound is filtered from excess paraform. Receive 56.5 g. (72% of theory) of light transparent in zkog

70

product with Pg, 1.4990, soluble in alcohol, aqueous alcohol (1: 1) when heated.

The individuality and purity of the obtained compound are controlled by thin layer chromatography on Silufol plates - UV-254 using aqueous alcohol as a solvent (1: 1) and water vapor as a solvent.

Found,%: C 53.58; 53.50, 4.25; 4.29; N 3.54-- 3.58.

H

С ,,, 0, о Calculated,%: J

53.60-, H 4.30; N 3.57.

The structure of the obtained compound is confirmed by the IR spectrum, in which the following characteristic bands of valence vibrations are observed: v-OH 3300,) -C 0-1670; -O-C-C1 680 cm, 1600; J —CH 1420-1460 cm.

4478132

The oak effect of the new compound is determined by the physico-mechanical and photographic parameters of the emulsion-gelatin layers (GOST 10691.0-73, GOST 5554-70, GOST 617425-76). In the finished positive emulsion before irrigation enter

ten

IS

20

25

thirty

35

40

45

50

55

tanning agent in the amount of 1 10 - 4,110 mol / l (alcohol-water solution) and this emulsion is poured on the laminated plates. The optimal concentration of the tanning agent, which determines the necessary thermal stability of the photo paper on the tenth day after watering (for Unibrom paper — 90 ° C), is 3–10 mol / l,

To speed up the tanning process, the emulsion layers are kept in a thermostat at elevated temperature (50i5 s). After certain periods of time (1,2,3 days), the layers are removed from the thermostat, cooled to room temperature and have physicomechanical properties (strength, deformation temperature) and photographic characteristics (photosensitivity, contrast ratio, optical density Byajm). The control of photographic properties on the plates is watered with the same emulsion without tanning agent.

Testing of physical and mechanical properties.

. The strength of the emulsion layer is determined by the magnitude of the dynamic load destroying the emulsion layer,

The test sample (6-9 cm) is kept for 5 minutes in distilled water at 20 ° C and placed under the rewinding rod; Such a determination is carried out in three places of the sample, and they are tested at least three times.

For the strength of the swollen emulsion layer take the arithmetic average value of all the determinations.

The temperature of the deforge units (mp. C) of the emulsion layer is determined by the disturbance of the surface of the emulsion layer when it is heated in water.

CH2

-T -C-CHoC-N 1 II

2 00

OH CH2 I CH201

as a dubitel emulsion

gelatinous photosensitive layers.

Sensitivity, 8

0.2. 20 20

Contrast ratio, 4.0

20

3.6

Claims (1)

35 claims Ν, Ν, Ν ¹ , Ν'-tetra- (2-hydroxy-6-chloro-3-hydroxymethylphenylmethyl) -malonic acid diamide of the formula as tanning agent of emulsion gelatin photosensitive layers. 5 1447813 6 Properties Control sample without tanning agent Sample dubbed ν, ν, ν ', ν'-tetraisopropoxymethyl) di - amidemethylphenyl malonic acid Ν, Ν, Ν ', ν'-tetra- (2-hydroxy-6-chloro-3-hydroxymethylphenylmethyl) -diamide of malonic acid Light sensitivity, B 0.2-10 ’ 20 20 20 Contrast Ratio 4.0 4.0 3.6 Optical density of the veil, 0.01 0.02 0.01 Mp, C 35 100 100 R ,, G 80 300 350