Zinc meso-trans-dihexadecyltetrabenzoporphyrinate

FIELD: chemistry.

SUBSTANCE: invention concerns a new compound, zinc meso-trans-dihexadecyltetrabenzoporphyrinate .

EFFECT: compound can be applied as a fat-soluble green colorant for solution dyeing of paraffin and polyethylene.

1 cl, 2 ex, 2 dwg

 

The invention relates to the chemical industry, namely, to the new connection - meso-TRANS-dihexadecylnaphthalene zinc, which can be used as a fat-soluble green dye for dyeing paraffins and polyethylene in the bulk material for thin-film microelectronics, as well as in other areas of science and technology.

The level of technology

Known tetrabenzoporphyrin zinc, which is a structural analogue [R.P. Linstead, Noble E.G. // J. Am. Chem. Soc. 1937. Part. II. P.933].

However, it cannot be used as a fat-soluble dye, as poorly soluble in polar organic solvents and insoluble in non-polar.

The closest structural analogues of the claimed compounds are zinc complexes of meso-tetraalkylfuranidones [Vinkobrnada, Sondaschule, VCCIO, Eaaaat. // CHC. 1984. No. 1. P.61].

However, these compounds, when used as a fat-soluble dyes does not allow you to get rich green color due to poor solubility in nonpolar organic solvents.

The invention

Inventive task was to search for new compounds, which are derived from tetrabenzoporphyrin zinc, which is about what was lagalo would be more soluble in nonpolar organic solvents, that would give the opportunity to use it as a fat-soluble dye.

The problem is solved meso-TRANS-dihexadecylnaphthalene zinc formula

The structure of this compound proved by data of elemental analysis, electronic, vibrational and NMR1N spectroscopy.

So, in the electronic absorption spectrum of the inventive meso-TRANS-dihexadecylnaphthalene zinc (figure 1) are in the visible area of the two main absorption bands in the region 427 nm and 627 nm. The IR spectrum of meso-TRANS-dihexadecylnaphthalene zinc (figure 2) has an absorption in the region 3060 cm-1corresponding to the fluctuations in the relations of C-H in the benzene rings isoindoline fragments, intense bands at 2923 and 2851 cm-1characterize fluctuations ties With-N in the alkyl substituents, the oscillation of the links C-N correspond to the band at 1464 cm-1. The NMR spectrum1N. meso-TRANS-dihexadecylnaphthalene zinc measured in CDCl3marked resonance of two meso-protons as singlet at 10.16 ppm, signals sixteen protons isoindoline fragments observed as multiplet in the region 7.77-7.41 ppm, a triplet at 2.75 ppm corresponds to resonance of the four protons of two alpha-methylene groups of the alkyl substituents, the singlet at 1.33 ppm, the character is not a resonance 56 protons of the remaining 28 methylene groups of the alkyl substituents and the triplet at 0.85 ppm corresponds to the resonance of six protons metal end groups of the alkyl substituents.

Information confirming the possibility of carrying out the invention.

To implement the method uses the following substances:

phthalimid - TU 6-09-3635-75;

stearic acid - GOST 9419-78

zinc acetate dehydrate - GOST 5823-78

zinc oxide - GOST 10262-73.

Method implemented in two stages.

Stage 1. Interaction phthalimide with stearic acid in the presence of zinc oxide according to the scheme

A mixture of 1.47 g (0.01 mol) of phthalimide, 2.84 g (0.01 mol) of stearic acid and 0.5 g of zinc oxide are heated at a temperature of 320°in a stream of argon for 1 h, then the reaction mass is then cooled, the excess carboxylic acid is removed by consecutive washing of the reaction mass to 10%potassium hydroxide solution and water. The residue is dissolved in 30 ml of chloroform and treated with 20 ml of 20%hydrochloric acid. The organic phase is separated, the solvent is removed, the residue is dissolved in carbon tetrachloride and chromatographic on a column filled with alumina II degree of activity by Brockmann (eluent - CCl4by collecting basic dark red zone.

The obtained 3,3/-[1(1-oxo-1H-isoindole-3-yl)heptageniidae]2,3-dihydro-1H-isoindole-1-it.

Yield 0.76 g (30%).

Waxy substance purple the CSOs color, soluble in benzene, CCl4, chloroform.

Electronic absorption spectrum (CCl4), λmaxnm (D/Dmax): 458 (0.84) 426 (1.00).

An NMR spectrum1H (CDCl3), δ, ppm: 10.92 (1H), 7.83-7.25 m (8H), 2.21 t (2H), 1.24 (28N), 0.84 t (3H).

Mass spectrum (ES)m/z (%): 498 [M]+(29), 368 (38), 331 (32), 160 (100).

Found, %: C 79.01; N, 8.55; N, 6.14. With33H42N2O2.

Calculated, %: C 79.48; N, 8.49; N, 6.25.

Stage 2. A mixture of 0.5 g (0.001 mol) of 3,3/-[1-(1-oxo-1H-isoindole-3-yl)heptageniidae]-2,3-dihydro-1H-isoindole-1-she and 1.5 g (0.007 mol) dihydrate zinc acetate is heated to 320°C and maintained at this temperature for 30 min, then the reaction mass is then cooled, dissolved in CCl4and chromatographic on a column filled with alumina II degree of activity by Brockmann (eluent mixture of CCl4- dioxane, 2:1 by volume), collecting the main green area.

Received meso-TRANS-dihexadecylnaphthalene zinc.

Yield 0.28 g (34%).

Waxy substance, dark green color, soluble in benzene, chloroform, CCl4, hexane, malorastvorima in acetone.

Electronic absorption spectrum (CCl4), λmaxnm (lgε): 402 (4.59), 427 (5.02), 579 (4.03), 626 (4.50).

IR-spectrum (solid layer), νcm-1: 3060 (CAr-H), 2923, 2851 (CAlk-N), 1464 (C-N).

An NMR spectrum1H (CDCl3), δ, ppm: 11.12 (2N), 7.777.41 m (N), 2.75 t (4H), 1.33 (N), 0.85 t (6N).

Found, %: C 80.22, H 8.76, N 5.12. With68H84N4Zn.

Calculated, %: C 79.85, H 8.28, N 5.48.

Example 1. The use of meso-TRANS-dihexadecylnaphthalene zinc as a dye for dyeing polyethylene in mass. Dyeing is carried out as follows: 2 g of granulated polyethylene mixed with 5 mg of meso-TRANS-dihexadecylnaphthalene zinc and maintained at 190°With stirring for 10 minutes

The sample is attached.

Example 2. The use of meso-TRANS-dihexadecylnaphthalene zinc as a dye for dyeing the wax. Dyeing is carried out as follows: 2 g of paraffin mixed with 5 mg of meso-TRANS-dihexadecylnaphthalene zinc and maintained at 130°With stirring for 10 minutes

The sample is attached.

Meso-TRANS-dihexadecylnaphthalene zinc formula



 

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