SU1608188A1 - Method of producing 3ъ,3ъ-dimethyl-6,8-dinitro-1ъ-propylspiro [2n-1-benzopyran-2,2ъ-indoline] - Google Patents

Abstract

The invention relates to heterocyclic substances, in particular the preparation of 3, 3, -dimethyl-6,8-dinitro-1-propylspiro [2-H-1-benzopyran-2,2-indoline], used as a photochromic substance in photosensitive materials for optical recording information. The goal is to make it possible to obtain a polydisperse crystalline film of the target product. To do this, 3,3-dimethyl-1-propyl-2 - [(3,5-dinitro-2-oxydophenyl-1) vinyl] indolenium on a substrate is sprayed at 450 ° C and a pressure in the range of ^10-6 ≤Р≥2 ^. 10 ^-5 mm Hg to obtain a 100% yield of the target product in the form of a homogeneous film, i.e. in solid form.

Description

films are recorded on a Specord M-40j spectrophotometer IR spectra are recorded on a Specord 1P-71 instrument. In the UV spectrum of the obtained polydisperse crystal film of compound I there is no absorption in the visible region of the spectrum, characteristic of compound II, there is a maximum around 350 nm, corresponding to the nitro-substituted chromium-free structure I.

In the IR spectrum of the obtained film of compound I, all the absorption bands characteristic of the spiropyranic structures are shown (1650 () of the pyranium ring); 1610, 1590 cm (H) of the aromatic system, conjugated with an unsaturated group); 910, 915,

935. cm- (C (--nwpo 0)) In addition, the spectrum obtained coincides with the CK spectrum of the solution of compound I.

The resulting film is photosensitive. When irradiated

With UV light - the irradiated field, the reaction occurs. I II is accompanied by staining.

Example 2. Analogously to Example 1, a polydisperse film of spiropyran I is obtained at an evaporation temperature of 480 ° C. At this temperature, the film is optically heterogeneous (the control is carried out using an interference microscope MP1-5).

Example 3c. Analogously to Example 1, a polydisperse film of spiropyran I is obtained at an evaporator temperature. The spray burden is 1800 s. The film is homogeneous.

EXAMPLE 4 Analogously to Example 1, a polydisperse film of spiropyran I is obtained at a temperature of sp. 450 C and residual pressure to orr. This pressure is the ultimate 5M residual pressure attained at the unit VUP-4 with an additional system of vacuum traps cooled with liquid nitrogen At. This product yield is 100%, the film is uniform.

And p and m e-p 5 “Similarly to example 1, a polydisperse film of spiropyran I is obtained at an evaporator temperature of 450 ° C and a residual pressure of 2 x X 10 Torr. In this case, the product yield is 100%, the film is homogeneous.

Example 6. Analogously to example 1, the merocyanine form of compound II is sprayed at an evaporator temperature of 450 ° C and a residual

0

five

0

five

0

five

0

five

pressure W Yu Torr. Under these conditions, the decomposition of the substance II occurs, and the decomposition products are deposited on the substrate.

As can be seen from the above examples, at pressures below 2 10 Torr, compound II decomposes, and the temperature ensures a uniform film.

Example 7 Comparative testing of photosensitive thin polydisperse films of Compound I obtained as a result of thermal vacuum synthesis with the photosensitivity of 1,3,3-trimethyl-6-nitroindoline spiropyran widely used in the series of spiropyrans.

The absorption coefficient of solid-phase polydisperse films is chosen to be $ 99% at a wavelength of 365 nm in order to ensure the full absorption of the activating light, the emission of a mercury lamp (А 365 nm) and to ensure that the measurement conditions are identical. The film under study is placed in a cuvette chamber with a Specord-UV-ViS spectrophotometer irradiation system. The dependence of the increase in optical density in the long-wavelength region, the spectrum on the time of irradiation with photoactive light is recorded. The relative rate constants of the direct photocolouring reaction are defined as the tg of the slope of the graph D (t) to the t axis at C- 0. Comparison of the rate constants of the direct photorecoating reaction of thin polydisperse films of spiropyran I and the standard (.1,3,3- trimethyl-6-nitroindolin spiropyran) is carried out with respect to the tg of the angles of inclination of the tangent D (t) to the t axis at. Photosensitivity is estimated by the speed of photocoloring about

As shown by comparative tests when irradiating with UV light from a mercury lamp (365 nm), 11 films of spiropyrans are stained, and the photo-dyeing rate of compound I is 1.9 times as high as the photo staining rate of the standard — M I

tg fC reference 1.9).

Along with photochemical activity, spiropyran I also possesses thermochromic properties. Thermal painting proceeds when the polydisperse film is heated up to 90-100 s. The Reference spiropyran does not possess thermochromic properties.

Thus, the proposed method allows to obtain 3, 3-dinetyl-6,8-dinitro-1-propyl spiro 2H-1-benzopyran-2,2-indoline in solid-phase form, which makes it possible to expand the scope of its use as a photosensitive compounds.

Claims (1)

Formula invented and The method of obtaining 3, 3-dimethyl--6,8-dinitro-1-propylspiro G2H-1-benzopyran-2,2-indindina formula NzS SN (I) using 3,3-dimethyl-1-pro-saw-2- (3,5-dinitro-2-oxidophenyl-1) vinyl indolenini formula (IG N02 sn-o 0 N02 characterized in that in order to obtain the desired product as a polydisperse crystalline film for expanding its non-X for use, the compound of formula (II) is sprayed onto the substrate in vacuum at a residual pressure of 10 P 2-10. mm Hg, and a temperature of 450 ° C.