Photocontrolled photochromic electroluminescent and electroconductive polymers for photonics

FIELD: chemistry.

SUBSTANCE: present invention pertains to new photochromic monomers

Alk=CH3-C10H21 X=Cl, Br, I, F, NH2, CH2OH, CH2Cl, CH2Br, CHO, CO2H, method of obtaining them, photochromic polymers- polyazomethines, which are reversibly photocontrolled due to introduction into their structure, of dihetarylenthane class photochromic fragments.

EFFECT: obtaining new photochromic photocontrolled polymers for designing new information technologies.

8 cl, 25 dwg, 15 ex

 

The technical field to which the invention relates.

The present invention relates to novel photochromic the monomers, the new photochromic polymers, methods for their preparation for the creation of new information technologies, photobrowser electroluminescense and conductive devices, including displays, photoperiodically polymer LEDs.

The level of technology

Currently an urgent task in the field of information technology is the creation of a flexible and projection displays, and light emitting diodes based on organic electroluminescense and conductive polymers using polyazomethines or condensing nitrogen-containing hetero-chain polymers. These polymer layers can serve as analogs of the invention.

The drawback of such polymeric materials is that their electroluminescence, and the conductivity is controlled by light.

At present, it was found that giving new properties of these polymers allows you to extend their functionality and practical use in Photonics.

The present invention consists in the synthesis of photochromic electroluminescense and conductive polymers whose properties by introducing in their structure photochromic fragments become reversible fotopro the act. Therefore, such polymers have enhanced functionality. Photochromic polymers of this type are suitable for use in the development of photochromic materials for different areas of Photonics ("Applied Photochromic Polymer Systems". McArdle, S. C., Ed. Blackie, Glasgow, 1992; Barachevsky VA "Photochromic organic media: state-of-the-art and future". Proc. SPIE, vol.2968, 77-86, 1997). The application of the proposed systems based on conductive and electroluminescense polymers with photochromic fragments opens up prospects for the development of displays of various types with dual photo - electric control. Thermally irreversible photochromic transformations associated compounds from the class of digitalisation successfully used to create a photochromic recording media, allowing for the development of three-dimensional bitwise (bitwise) optical random-access memory (M. Irie. "Dihetarylethenes for Memories and Switches". Chem. Reviews, vol.100, 1685-1716, 2000). The inclusion of photochromic fragments in the polymer chain can be used to improve developed photochromic recording medium by increasing the concentration of photochromic molecules in the polymer environment and a sharp reduction in their diffusion movement. The result of such improvements is a significant increase in information capacity. The lack of mutual thermal transformations of two forms of the molecules of digitalisation used is as photochromic fragments of polymers, expands the scope of a reversible photochromic photoperiodically radiation (J.A.Delaire, .Nakatani. "Linear and Nonlinear Optical Properties of Photochromic Molecules and Materials". Chem. Reviews, vol.100, 1817-1845, 2000).

The problem is solved due to the fact that as photochromic monomers for obtaining photobrowser electroluminescense and electrically conductive polymers are the following functional compounds from the class of digitalisation (1):

Alk=CH3-C10H21

X=Cl, Br, I, F, NH2CH2HE, CH2Cl, CH2Br, CHO, CO2N

Photochromism of diarylethene (DAE) is reversible photocyclization, i.e. in the photoinduced transition from the open form (PF) AND in the cyclic form (ZF)

Because it alters the paired communication system in photochromic molecules, they allow you to control the specified properties of the polymers.

The present invention is directed to new functional dietrelated (1), the retrieval method, the photochromic polyazomethine, photochromic Cardo poliolefine and methods for their production, to use as a photochromic fragments of new functional is x digitalisation (1). The use of these photochromic compounds provides polyazomethines based on them reversible fotoralerei electroluminescent and conductive properties due to photochromic transformations of polymer fragments, altering the degree of electronic coupling.

A method of obtaining a photochromic monomers include acylation derivative benzothiophene (and peroration, thienothiophene, pornotopia) dichlorohydrin glutaric acid in methylene chloride in the presence of aluminum chloride and subsequent reductive cyclization of the obtained diketones under the action of TiCl4, Zn in THF in the presence of pyridine, with further formirovanie reaction products dichlormethane ether in nitrobenzene in the presence of aluminum chloride.

Photochromic polyazomethine based photochromic monomers (1) have the following General structural formula and molecular weight from 25,000 to 50,000:

where Alk=CH3-C10H21

y=-C=N-; -N=C-

where n=50-100.

The retrieval method comprises the polycondensation in a solution of monomers according to claim 1 with aromatic diamines or dialdehyde when temperature is from about 20 to 200° C.

Under Cardo polymers understand the polymers, the Central carbon atom which is part of the surround lateral cyclic (Cardo) group.

Photochromic Cardo polyazomethine in accordance with the present invention have a molecular weight of 30,000 to 50,000 and General structural formula:

where Alk=CH3-C10H21

y=-C=N-; -N=C-

where n=50-100.

The retrieval method comprises the polycondensation in solution photochromic monomer (1) with Cardo aromatic diamines or dialdehyde at a temperature of about 20-200°C.

Analysis of the known scientific-technical and patent literature showed that the full set of features that characterize these technical solutions that were not previously known, i.e. the proposed solutions meet the criterion of "novelty".

The invention is illustrated by examples and drawings.

Figure 1 shows the structural formulas photochromic monomers used to produce the photochromic copolymers and polymers.

Figure 2 illustrates the design of photochromic transformations of digitalisation.

Figure 3 presents a scheme of obtaining photochromic monomer 5 from the class of the inventive photochromic functional connections.

Figure 4 shows with entry absorption of open source And (curve 1) and photoinduced In (curves 2-7) photochromic monomer 5 in toluene before (1) and after exposure to UV light increases the exposure accordingly.

Figure 5 presents the kinetic curves (D(t) is the optical density) of photocreative UV light (curve 1) and photobleaching visible light (curve 2) solution of the photochromic monomer 5 in toluene at the wavelength of maximum absorption band of the cyclic forms of the Century

Figure 6 shows a scheme for obtaining a photochromic monomer 8 from the class of the inventive photochromic functional connections.

Figure 7 shows a scheme for obtaining a photochromic monomer 10 from the class of the inventive photochromic functional connections.

On Fig presents the scheme of obtaining photochromic monomer 17 from the class of the inventive photochromic functional connections.

Figure 9 shows a scheme for obtaining a photochromic monomer 20 from the class of the inventive photochromic functional connections.

Figure 10 presents the scheme of obtaining photochromic monomer 25 from the class of the inventive photochromic functional connections.

Figure 11 shows a scheme for obtaining a photochromic monomer 31 from the class of the inventive photochromic functional connections.

On Fig presents the scheme of obtaining polyazomethine III.

On Fig shows absorption spectra of open source And the shape (curve 1) and scattering (curve 2) after UV irradiation through a glass filter UFS-2 and after irradiation of visible light through clanny filter LGL-12 (curve 3) for films of photochromic polymer III in polycarbonate (4 wt.% of dry weight of polymer).

On Fig presents the kinetic curves photocreative UV light through a glass filter UFS-2 (curve 1) and photobleaching visible light through a glass filter LGL-12 (curve 2) for films of photochromic polymer III in polycarbonate (4 wt.% of dry weight of polymer) at the wavelength of maximum absorption band of the cyclic forms of the Century

On Fig presents the structure of the photochromic polymer IIIa.

On Fig presents the structure of the photochromic polymer IIIb.

On Fig presents the structure of the photochromic polymer IIIc.

On Fig presents the structure of the photochromic polymer IIId.

On Fig scheme of the synthesis of the photochromic polymer V.

On Fig shows absorption spectra of open source And the shape (curve 1) and photoinduced forms after exposure to UV light through a glass filter UFS-2 (curve 2)and after irradiation of visible light through a glass filter LGL-12 (curve 3) for films of photochromic polymer V polycarbonate (4 wt.% of dry weight of polymer).

On Fig presents the kinetic curves photocreative UV light through a glass filter UFS-2 (curve 1) and photobleaching visible light through a glass filter LGL-12 (curve 2) for films of photochromic polymer V polycarbonate (4 wt.% of dry weight of polymer) in the wavelength band maximum will is of circular form Century.

On Fig presents the structure of the photochromic polymer Va.

On Fig presents the structure of the photochromic polymer VI

On Fig presents the structure of the photochromic polymer VII.

On Fig presents the structure of the photochromic polymer VIII.

Information confirming the possibility of carrying out the invention, but not limit the amount of stated claims.

Example 1

Photochromic monomers 1,2-bis(2-methyl-6-formyl-1-benzothiophen-3-yl)cyclopentene 5A-e class used photochromic monomers containing benzothiophene fragments associated cyclopentenone bridge, was synthesized on the basis of benzothiophenes 2A-e according to the scheme shown in figure 3.

Source benzothiophene 2A-e were obtained by the described methods: 2-methylbenzoate (2A) (Synthesis of sulfides, teofanov and thiol type compounds found in crude oil. Edited Enterology. M.: "Nauka", 1988, s), 2,4-dimethylbenzamide and 2.7-dimethylbenzamide (2b, 2C) (Monatsh. Chem. 1960, 91, 1070), 2,4-dimethylbenzamide and 2,6-dimethylbenzamide (2d, 2e) (J.Chem. Soc., Chem. Com. 1974, 5, 174).

Synthesis of 1,2-bis(2-methyl-6-formyl-1-benzothiophen-3-yl)Cyclopentanol 5A-e included acylation of benzothiophenes 2A-e dichlorohydrin glutaric acid in methylene chloride in the presence of aluminum chloride and subsequent reductive cyclization of the obtained diketones 3A-e, which ex is started topics that compounds 4A-e were obtained from 60-73% yield by cyclization of diketones 3A-e under the action of TiCl4, Zn in THF in the presence of pyridine, while the literature describes the connection is obtained by cyclization of 4A diketone 3A under the action of TiCl4, Zn in THF to yield 54% (Synthesis 1998, 1092-1094). Subsequent formirovanie products 4A-e dichlormethane ether in nitrobenzene in the presence of aluminum chloride led to the formation of 1,2-bis(2-methyl-6-formyl-1-benzothiophen-3-yl)Cyclopentanol 5A-E.

The General scheme for the synthesis of 1,5-bis-(methyl-1-beautifun-3-yl)pentane-1,5-diones 3A-e

To a well stirred mixture of 20.2 mmol of methylbenzamide 2A-e and 10.1 mmol of dichlorohydrin glutaric acid in 50 ml of methylene chloride are added at 0°From 42.5 mmol of anhydrous aluminum chloride. The reaction mass is stirred at room temperature for 3-6 hours. Poured on ice water, extracted with methylene chloride (3×100 ml), the collected organic layers washed with aqueous solution of NaHCO3, dried over magnesium sulfate, the solvent evaporated under vacuum. The residue is recrystallized from hexane.

1,5-Bis-(2-methyl-1-benzothiophen-3-yl)pentane-1,5-dione 3A

Obtain 3.25 g of product 3A (82%), TPL 165-167°With (hexane: chloroform, 6:1, by vol.). Mass spectrum, m/z: 392, [M]+. An NMR spectrum1H (DMSO-d6, δ, ppm, J/Hz): 2,0-2,2 (m, 2H, CH2), 2,62 (s, 6N, 2×CH3), 3,1-3, (USM, 4H, 2×CH2), 7,3-7,5 (USM, 4H, 4×CHarene), a 7.85-8,2 (USM, 4H, 4×CHarene). Found (Percent): C, 70,42; N, 5,16; S, 16,29. With23H20O2S2. Calculated (%): C, 70,37; N, 5,14; S, 16,34.

1,5-Bis-(2,5-dimethyl-1-benzothiophen-3-yl)pentane-1,5-dione 3b

Obtain 3.57 g of product (3b) (84%), TPL 171-173°With (hexane: chloroform, 6:1, by vol.). Mass spectrum, m/z: 420, [M]+. An NMR spectrum1H (DMSO-d6, δ, ppm, J/Hz): 2,0-2,3 (m, 2H, CH2), is 2.40 (s, 6N, 2×CH3), 2,62 (s, 6N, 2×CH3), a 2.75-3,2 (USM, 4H, 2×CH2), 7,4-8,1 (USM, 6N, 6×CHarene). Found (Percent): C, 71,45; N, 5,77; S, 15,20. C25H24O2S2. Calculated (%): C, 71,39; N, 5,75; S, 15,25.

1,5-Bis-(2,7-dimethyl-1-benzothiophen-3-yl)pentane-1,5-dione 3s

Get 3,61 g of the product (3C) (85%), TPL 159-161°With (hexane: chloroform, 6:1, by vol.). Mass spectrum, m/z: 420, [M]+. An NMR spectrum1H (DMSO-d6, δ, ppm, J/Hz): of 2.1-2.4 (m, 2H, CH2), of 2.56 (s, 6N, 2×CH3), to 2.66 (s, 6N, 2×CH3), 2,8-3,2 (USM, 4H, 2×CH2)and 7.1-7.5 (USM, 4H, 4×CHarene), an 8.0-8.3 (USM, 2H, 2×CHarene). Found (Percent): C, 71,43; N, 5,73; S, 15,29. With25H24O2S2. Calculated (%): C, 71,39; N, 5,75; S, 15,25.

1,5-Bis-(2,4-dimethyl-1-benzothiophen-3-yl)pentane-1,5-dione 3d

Gain of 3.32 g of the product (3d) (78%), TPL 156-158°With (hexane: chloroform, 6:1, by vol.). Mass spectrum, m/z: 420, [M]+. An NMR spectrum1H (DMSO-d6, δ, ppm, J/Hz): 2,0-2,3 (m, 2H, CH2), 2,62 (s, 6N, 2 on; CH3), of 2.64 (s, 6N, 2×CH3), 2,9-3,2 (USM, 4H, 2×CH2), 7,2-8,0 (USM, 6N, 6×CHarene). Found (Percent): C, 71,35; N, 5,77; S, 15,30. C25H24About2S2. Calculated (%): C, 71,39; N, 5,75; S, 15,25.

1,5-Bis-(2,6-dimethyl-1-benzothiophen-3-yl)pentane-1,5-dione 3E

Get 3,66 g of the product (3E) (86%), TPL 171-173°With (hexane: chloroform, 6:1, by vol.). Mass spectrum, m/z: 420, [M]+. An NMR spectrum1H (DMSO-d6, δ, ppm, J/Hz): 2,05-of 2.25 (m, 2H, CH2), 2,44 (s, 6N, 2×CH3), 2,62 (s, 6N, 2×CH3), a 2.9-3.15 in (USM, 4H, 2×CH2), 7,25 to 7.4 (USM, 2H, 2×CHarene), 7,7-7,9 (USM, 4H, 2×CHarene). Found (Percent): C, 71,47; N, 5,73; S, 15,31. C25H24O2S2. Calculated (%): C, 71,39; N, 5,75; S, 15,25.

General methods of synthesis of 1,2-bis(2-methyl-1-benzothiophen-3-yl)cyclopentene 4

To a well stirred suspension of 7.93 mmol of zinc in fresh anhydrous THF (50 ml) at -10°With under argon is added dropwise 2.8 ml of TiCl4. After the addition, the reaction mixture is heated under argon for 1 h Cooled to 20°and add 12.8 mmol diketone 3A-e and anhydrous pyridine (5 ml). Boil under argon for another 20 hours Poured into 10% K2CO3(150 ml) and the aqueous layer was extracted with Et2O (5×100 ml). The collected organic extracts are dried MgSO4and distilled under vacuum. The residue is cleaned using flash chromatography on silica gel (Merck, 0,063-0,1), eluent PHE is Romany ether (40/70)-AcOEt (10:1, vol.).

1,2-bis(2-methyl-1-benzothiophen-3-yl)cyclopentan 4A

Obtain 2.76 g of the product 4A (60%) with TPL 186,5-187,5°, TPL lit. 187-188°With (Synthesis 1998, 1092-1094).

1,2-bis(2,5-dimethyl-1-benzothiophen-3-yl)cyclopentan 4b

Get 3,19 g of the product (4b) (69%), TPL 165-167°With (hexane: chloroform, 6:1, by vol.). Mass spectrum, m/z: 388, [M]+. An NMR spectrum1H (DMSO-d6, δ, ppm, J/Hz): 2,08-2,23 (USM, 2H, CH2), is 2.40 (s, 6N, 2×CH3), 2,52 (s, 6N, 2×CH3), 3,09-3,24 (USM, 4H, 2×CH2), 7,16 (m, 2H, Harene) 7,31 (m, 2H, Harene) of 7.55 (m, 2H, Harene). Found (Percent): C, 77,30; N, 6,21; S, 16,43. C25H24S2. Calculated (%): C, 77,35; N, 6,23; S, 16,38.

1,2-bis(2,7-dimethyl-1-benzothiophen-3-yl)cyclopentan 4C

Get 3,37 g of the product (4C) (73%), TPL 174-176°With (hexane: chloroform, 6:1, by vol.). Mass spectrum, m/z: 388, [M]+. An NMR spectrum1H (DMSO-d6, δ, ppm, J/Hz): 2,08-2,23 (USM, 2H, CH2), 2,50 (s, 6N, 2×CH3), 2,52 (s, 6N, 2×CH3), 3,09-3,24 (USM, 4H, 2×CH2), 7,02 (m, 2H, Harene), 7,12 (m, 2H, Harene), 7,21 (m, 2H, Harene). Found (Percent): C, 77,32; N, 6,24; S, 16,45. C25H24S2. Calculated (%): C, 77,25; N, 6,26; S, 16,50,

1,2-bis(2,4-dimethyl-1-benzothiophen-3-yl)cyclopentan 4d

Get 2,82 g of the product (4d) (61%), TPL 171-173°With (hexane: chloroform, 6:1, by vol.). Mass spectrum, m/z: 388, [M]+. An NMR spectrum1H (DMSO-d6that δ, ppm, J/Hz): 2,08-2,23 (USM, 2H, CH2), 2,52 (s, 6N, 2×CH3), 2,69(s, 6N, 2×CH3), 3,09-3,24 (USM, 4H, 2×CH2), 7,00 (m, 2H, Harene), 7,20 (m, 2H, Harene), 7,52 (m, 2H, Harene). Found (Percent): C, 77,33; N, 6,24; S, 16,48. C25H24S2. Calculated (%): C, 77,26; N, 6,23; S, 16,52.

1,2-bis(2,6-dimethyl-1-benzothiophen-3-yl)cyclopentan 4E

Obtain 3.0 g of product (4E) (65%), TPL 184-186°With (Mass spectrum, m/z: 388, [M]+. An NMR spectrum1H (DMSO-d6, δ, ppm, J/Hz): 2,21-2,23 (USM, 2H, CH2), 2,44 (s, 6N, 2×CH3), 2,52 (s, 6N, 2×CH3), 3,09-3,24 (USM, 4H, 2×CH2), 7,18 (m, 2H, Harene), 7,38 (m, 2H, Harene), 7,53 (m, 2H, Harene). Found (Percent): C, 77,30; N, 6,24; S, 16,44. C25H24S2. Calculated (%): C, 77,41; N, 6,22; S 16,50.

General methods of synthesis of 1,2-bis(formyl-1-benzothiophen-3-yl)Cyclopentanol 5A-e

To a stirred solution of 3.33 mmol of 1,2-bis(dimethyl-1-benzothiophen-3-yl)cyclopentene 4A-e in nitrobenzene (25 ml) at 0°add 50 mmol dichlorodifluoro ether and 13,35 mmol of anhydrous aluminum chloride, stirred for 30 min at 0°and 20 hours at room temperature. The reaction mixture was poured into ice water and the product extracted with ethyl acetate, washed with water, dried with magnesium sulfate. After distillation of nitrobenzene under vacuum the product was then purified using column chromatography (Silica Gel, 0,063-0,1), eluent petrol. ether (40/70):ethyl acetate (6:1, by vol.).

1,2-bis(2-methyl-6-formyl-1-benzothiophen-3-yl)cyclopentan 5 is

Obtain 0.56 g of the dialdehyde (5A) (40%), TPL 196-197°With (hexane: chloroform, 6:1, by vol.). Mass spectrum, m/z: 416, [M]+. An NMR spectrum1H (DMSO-d6, δ, ppm, J/Hz): 2,25 (m, 6N, 2×CH3), 2,97 (USS, 6N, 3×CH2), a 7.6-8.5 in (USM, 6N, CHarene), 9,98 (USS, 2H, 2×SNO). Found (Percent): C, 72,16; N, 4,86; S, 15,34. C25H20O2S2. Calculated (%): C, 72,08; N, 4,84; S, 15,40.

The obtained compound 5A was dissolved in toluene at a concentration of C=2.10-4M. absorption Spectra of forms a and b were measured on the spectrophotometer Cary 50 (Varian) immediately after dissolution (figure 4, CR) and after exposure to UV light mercury lamps DRSH-250 through a glass filter UFS-2 of the standard set of glass optical filters (4, CR-7). Photochromic monomer is characterized by a high reversibility (cycles) photochromic transformations, as evidenced by the presence isometrically point on the curves of absorption (figure 4). Then measured the change in optical density (kinetics) of the solution at the maximum of the absorption band of the cyclic form under the action of the same UV light (a process photocreative) (figure 5, kr) and after reaching the state of equilibrium under the action of visible light of the same light source, passed through a glass filter LGL-12 (the process of photobleaching) (figure 5, kr). From the spectral-kinetic data shows that the connection oblad is no acceptable for practical use photochromic properties.

1,2-bis (2,5-dimethyl-6-formyl-1-benzothiophen-3-yl)cyclopentan 5b

Obtain 0.71 g of the dialdehyde (5b) (48%), TPL 181-183°With (hexane: chloroform, 6:1, by vol.). Mass spectrum, m/z: 444, [M]+. An NMR spectrum1H (DMSO-d6, δ, ppm, J/Hz): 2,0-2,4 (m, 2H, CH2), to 2.55 (s, 6N, 2×CH3), 2,86 (s, 6N, 2×CH3), 2,95-of 3.25 (m, 4H, 2×CH2), 7,40 (USS, 2H, 2×CHarene), 8,24 (USS, 2H, 2×CHarene), to 10.09 (USS, 2H, 2×SNO). Found (Percent): C, 73,03; N, 5,43; S, 14,37. C27H24O2S2. Calculated (%): C, 72,94; N, 5,44; S, 14,42.

1,2-bis(2,7-dimethyl-6-formyl-1-benzothiophen-3-yl)cyclopentan 5s

Obtain 0.96 g of the dialdehyde (5C) (65%), TPL 163-165°With (hexane: chloroform, 6:1, by vol.). Mass spectrum, m/z: 444, [M]+. An NMR spectrum1H (DMSO-d6, 5, ppm, J/Hz): of 2.05 to 2.35 (m, 2H, CH2), 2,50 (s, 6N, 2×CH3), only 2.91 (s, 6N, 2×CH3), a 3.0 to 3.25 (m, 4H, 2×CH2), 7,32 (USD, 2H, 2×CHarene), 7,79 (USD, 2H, 2×CHarene), 10,10 (USS, 2H, 2×SNO). Found (Percent): C, 72,90; N, 5,43; S, 14, 48mm. C27H24O2S2. Calculated (%): C, 72,94; N, 5,44; S, 14,42.

1,2-bis(2,4-dimethyl-5-formyl-1-benzothiophen-3-yl)cyclopentan 5d

Gain of 1.05 g of the dialdehyde (5d) (68%), TPL 187-189°With (hexane: chloroform, 6:1, by vol.). Mass spectrum, m/z: 444, [M]+. An NMR spectrum1H (DMSO-d6, δ, ppm, J/Hz): 2,0 to 2.35 (m, 2H, CH2), to 2.54 (s, 6N, 2×CH3), 2,97 (s, 6N, 2×CH3), 3,1-3,3 (m, 4H, 2×CH2), 7,47 (USD, 2H, 2×CHarenearene), 10,31 (USS, 2H, 2×SNO). Found (Percent): C, 72,99; N, The 5.45; S, 14,38. C27H24O2S2. Calculated (%): C, 72,94; N, 5,46; S, 14,42.

1,2-bis (2,6-dimethyl-5-formyl-1-benzothiophen-3-yl)cyclopentan 5e

Gain of 0.77 g of the dialdehyde (5e) (52%), TPL 201-203°With (hexane: chloroform, 6:1, by vol.). Mass spectrum, m/z: 444, [M]+. An NMR spectrum1H (DMSO-d6, δ, ppm, J/Hz): 2,0-2,4 (m, 2H, CH2), 2,52 (s, 6N, 2×CH3), 2,85 (s, 6N, 2×CH3), a 3.0 to 3.35 (m, 4H, 2×CH2), 7,31 (USS, 2H, 2×CHarene), 8,42 (USS, 2H, 2×CHarene), 10,28 (USS, 2H, 2×SNO). Found (Percent): C, 73,01; N, 5,46; S, 14,35. C27H24O2S2. Calculated (%): C, 72,94; N, 5,44; S, 14,42.

Example 2

1. The technique of synthesis of 1,2-bis(2-decyl-6-formyl-1-benzothiophen-3-yl)cyclopentene 5g.

1,2-bis(2-decyl-6-formyl-1-benzothiophen-3-yl)cyclopentan 5g get analgine 1,2-bis(2-methyl-6-formyl-1-benzothiophen-3-yl)cyclopentene 5A-e (see Example 1) using as starting compound 2-deliberation (see the General scheme of figure 3).

The target 1,2-bis(2-decyl-6-formyl-1-benzothiophen-3-yl)cyclopentan 5g obtained as an amorphous powder.

Mass spectrum, m/z: 668, [M]+. An NMR spectrum1H (DMSO-d6, δ, ppm, J/Hz): 0.88 (Tr, 6N, 2×CH3); 1.40-1.8 (m N, 8×CH2) 2.97 (USS, 6N, 3×CH2), 3.20 (m, 4H, 2×CH2); 7.6-8.5 (USM, 6N, CHarene), 9.98 (USS, 2H, 2×SNO). Found (Percent):C, 77.16; N, 8.86; S, 9.34. With43H56O2S2. Calculated (%): C, 77.25; H, 8.38; S, 9.58.

2. The technique of synthesis of 1,2-bis(2-methyl-6-carboxy-1-benzothiophen-3-yl)cyclopentene 8. Synthesis of lead according to the scheme shown in Fig.6.

Synthesis of dictaphone 7

To a solution of 0.75 g (2.1 mmol) of compound 4A in 15 ml of CH2Cl2added 0.75 g (5.6 mmol) AlCl3the reaction mixture was cooled to a temperature of 5°and then pricipal 5.5 mmol of acid chloride 6. Stirred the mixture at a temperature of 5-15°C for 3 hours, then added 50 ml of water and was extracted with 3×50 ml of ethyl acetate. The organic layer was dried over MgSO4and then was evaporated. The residue was cleaned through column chromatography (4:1 petroleum ether - ethyl acetate). The yield of compound 7 was 0.45 g (39%). TPL=158-162°C.

Synthesis of decollate 8

To a solution of 0.09 g (0.16 mmol) of compound 7 in 3 ml of dioxane was added 0.035 g (0.8 mmol) of NaOH in 3 ml of water and 0.5 ml of N2O2(30% solution in N2O). The reaction mixture was stirred for 10 h, then was added 10 ml of water and was acidified solution to pH=4 with diluted sulfuric acid. Precipitated amorphous precipitate was filtered and possile. The output connection 8 72%.

Mass spectrum, m/z: 448, [M]+. An NMR spectrum1H (DMSO-d6, δ, ppm, J/Hz): 2.26 (m, 6N, 2×CH3), 2.93 (USS, 6N, 3×CH2), 7.6-8.5 (USM, 6N, CHarene). Found (percent): C, 66.46; H, 4.86; S, 14.34. C25H20O4 S2. Calculated (%): C, 66.70; H, 4.46; S, 14.28.

3. The technique of synthesis of 1,2-bis(2-methyl-6-metiloksi-1-benzothiophen-3-yl)cyclopentene 9. Synthesis of lead according to the scheme shown in Fig.7.

Recovery of MDA 5A was performed by standard methods NaBH4in methanol. Output connection 9 to 52%.

Mass spectrum, m/z: 420, [M]+. An NMR spectrum1H (DMSO-d6, δ, ppm, J/Hz): 2.28 (m, 6N, 2×CH3), 2.87 (USS, 6N, 3×CH2), 4.56 (USS, 4H, 2×CH2), 7.6-8.5 (USM, 6N, CHarene). Found (percent): C, 71.76; H, 5.86; S, 15.34. C25H20O4S2. Calculated (%): C, 71.43; H, 5.71; S, 15.23.

4. The technique of synthesis of 1,2-bis(2-methyl-6-chloromethyl-1-benzothiophen-3-yl)cyclopentene 10. Synthesis of lead according to the scheme shown in Fig.7.

Getting dichloride 10 was performed by standard methods in the two-phase system of chloroform - 32% hydrochloric acid. Yield 67%.

An NMR spectrum1H (DMSO-d6, δ, ppm, J/Hz): 2.25 (m, 6N, 2×CH3), 2.97 (USS, 6N, 3×CH2), 4.45 (C., 4H, 2×CH2), 7.6-8.5 (USM, 6N, CHarene). Found (percent): C, 65.76; H, 4.96; Cl 15.92, S, 14.34. C25H20Cl2S2. Calculated (%): C, 65.79; H, 4.82; Cl 15.35, S, 14.03.

Example 2A

Photochromic 1,2-bis(2-methyl-5-formyl-4H-thieno[3,2-b]pyrrol-3-yl)cyclopentan 17 class used photochromic monomers were synthesized according to the scheme shown in Fig.

Methyl ester 2-azido-3-(5'-methyl-2'-thienyl)acrylic acid 12

To a mixture of sodium methylate prepared from (1.8 g, to 78.3 mmol) of sodium and 30 ml of abs. methanol, and (22,8 g, 0.2 mol) methyl ester etidocaine acid with stirring and the temperature-5-0°With added 30 mmol of methylthiophenethylamine 11 [methylthiocarbamate 11 was synthesized according to the method described in Orsanic Syntheses, Coll. Vol.4, p.915 (1963); Vol.31. p.108 (1951)]. The mixture was stirred at 0°With 30 minutes and 2 hours at room temperature. Add an aqueous solution of saturated NH4Cl and stirred for 10 minutes. The precipitation is filtered off and dried. Exit 11 (76%), TPL 51° (div.). Mass spectrum, m/z: 223, [M]+. An NMR spectrum1H (CDCl3that δ, ppm): 2.55 (s, 3H, CH3), 3.80 (s, 3H, CH3O), 6,74 (s, 1H, CH), 7.10 (s, 1H, CHarene), 7.15 (s, 1H, CHarene). IR-spectrum (KBr tablet with), ν/cm-1: 2120 OCS (N3). Found (percent): C, 48.52; H, 4.20; N, 19.02; S, 14.81. C9H9N3O2S. Calculated (%): C, 48.42; H, 4.06; N, at 18.82; S, 14.36.

Methyl ester of 2-methyl-4H-thieno[3,2-b]pyrrole-5-carboxylic acid 13

A solution of 30 mmol of methyl ether 2-azido-3-(thienyl-2')-acrylic acid 12 in 50 ml of toluene is boiled for 3 hours. The precipitation is filtered off, the mother liquor evaporated under vacuum and recrystallized from toluene. Precipitation unite. Exit 13 (95%), TPL 189-190°C (from toluene). Mass spectrum, m/z: 195, [M]+. An NMR spectrum1H (CDCl3that δ, ppm): 2.54 (who, 3H, CH3), 3.82 (s, 3H, CH3Oh), 6.65 (s, 1H, CHarene), 7.06 (s, 1H, CHarene), 9.25 (USS, 1H, NH). Found (percent): C, 55.40; H, 4.65; N, 7.23; S, 16.53. C9H9NO2S. Calculated (%): C, 55.37; H, 4.65; N, 7.17; S, 16.42.

1,5-bis-(2-methyl-5-methoxycarbonyl-4H-thieno[3,2-b]pyrrol-3-yl)pentane-1,5-dione 14

To a well stirred mixture of 20.2 mmol of thienopyrrole 13 and 10.1 mmol of dichlorohydrin glutaric acid in 50 ml of methylene chloride are added at 0°42.5 mmol of anhydrous aluminum chloride. The reaction mass is stirred at room temperature for 6 hours. Poured on ice water, extracted with methylene chloride (3×100 ml), the collected organic layers washed with aqueous solution of NaHCO3, dried over magnesium sulfate, the solvent evaporated under vacuum. The residue is recrystallized from hexane. Exit 14 (82%), TPL 175-177°With (hexane; chloroform, 6:1, by vol.). Mass spectrum, m/z: 486, [M]+. An NMR spectrum1H (DMSO-d6, δ, ppm, J/Hz): 2.0-2.2 (m, 2H, CH2), 2.62 (s, 6N, 2×CH3), 3.1-3.2 (USM, 4H, 2×CH2), 3.82 (s, 6N, 2×CH3Oh), 6.84 (s, 2H, 2×CHarene), 9.25 (USS, 2H, 2×NH). Found (percent): C, 56.64; H, 4.42; N, 5.82. With23H2N2O6S2. Calculated (%): C, 56.78; H, 4.56; N, 5.76.

1,2-bis(2-methyl-5-methoxycarbonyl-4H-thieno[3,2-b]pyrrol-3-yl)cyclopentan 15

To a well stirred suspension 7.93 mmol of zinc in fresh anhydrous THF (TH) (50 ml) at -10° With under argon is added dropwise 2.8 ml of TiCl4. After the addition, the reaction mixture is heated under argon for 1 h Cooled to 20°and add 12.8 mmol diketone 14 and anhydrous pyridine (5 ml). Boil under argon for another 20 hours Poured into 10% K2CO3(150 ml) and the aqueous layer was extracted with Et2O (5×100 ml). The collected organic extracts are dried MgSO4and distilled under vacuum. The residue is cleaned using flash chromatography on silica gel (Merck, 0.063-0.1), eluent petroleum ether (40/70)-AcOEt (10:1, by vol.). Exit 10 (60%) with TPL 196.5-has 197.5°C. Mass spectrum, m/z: 454, [M]+. An NMR spectrum1H (DMSO-d6, δ, ppm, J/Hz): 1.9-2.1 (m, 2H, CH2), 2.42 (s, 6N, 2×CH3), 3.0-3.1 (USM, 4H, 2×CH2), 3.71 (s, 6N, 2×CH3Oh), 6.63 (s, 2H, 2×CHarene), 9.12 (USS, 2H, 2×NH). Found (percent): C, 60.64; H, 4.72; N, 6.22. With23H22N2O4S2. Calculated (%): C, 60.77; H, 4.88; N, 6.16.

1,2-bis(2-methyl-5-oximeter-4H-thieno[3,2-b]pyrrol-3-yl)cyclopentan 16

To a well stirred solution of compound 15 (12 mmol) in 5 ml of ether was added LiAlH4(10 mmol) and the reaction mixture was stirred for 1 hour. When cooled, added water, and the separated ether layer. The solvent was distilled, the resulting product was cleaned using flash chromatography on silica gel (Merck, 0.063-0.1), eluent - petroleum ether (40/70)-AcOEt (10:1, by vol.). Exit 16 (59%) with TPL 166.5-167.5°C. Mass when ECtHR, m/z: 398, [M]+. An NMR spectrum1H (DMSO-d6, δ, ppm, J/Hz): 1.9-2.1 (m, 2H, CH2), 2.42 (s, 6N, 2×CH3), 3.0-3.1 (USM, 4H, 2×CH2), 4.82 (s, 4H, 2×CH2), 6.61 (s, 2R, 2×CHarene), 9.11 (USS, 2H, 2×NH). Found (percent): C, 63.34; H, 5.62; N, 7.12. C; C21H22N2O2S2. Calculated (%): C, 63.29; H, 5.56; N, 7.03.

1,2-bis(2-methyl-5-formyl-4H-thieno[3,2-b]pyrrol-3-yl)cyclopentan 17

To a well stirred solution of compound 16 (12 mmol) in 20 ml of methylene chloride was added to the complex of chromium trioxide with two molecules of pyridine (72 mmol) and the reaction mixture was stirred for 30 min at room temperature. The solvent was distilled, the resulting product was cleaned using flash chromatography on silica gel (Merck, 0.063-0.1), eluent - petroleum ether (40/70)-AcOEt (10:1, by vol.). Exit 17 (28%) as a viscous oil. Mass spectrum, m/z: 394, [M]+. An NMR spectrum1H (DMSO-d6, δ, ppm, J/Hz): 1.9-2.0 (m, 2H, CH2), 2.40 (s, 6N, 2×CH3), 3.0-3.1 (USM, 4H, 2×CH2), 6.58 (s, 2H, 2×CHarene), 9.18 (USS, 2H, 2×NH), 10.02 (USS, 2H SNO). Found (percent): C, 63.66; H, 4.62; N, 7.15. C21H18N2O2S2. Calculated (%): C, 63.96; H, 4.57; N, 7.11.

Example 3

Method for producing 1,2-bis[N-methyl(2-methyl-5-formyl-4H-thieno[3,2-b]pyrrol-3-yl)]cyclopentene 20. The synthesis was carried out according to the scheme shown in Fig.9.

1,2-bis[N-methyl(2-methyl-5-methoxycarbonyl-4H-thieno[3,-b]pyrrol-3-yl)]cyclopenten 18 received the standard method for methylation 15 iodide stands.

Mass spectrum, m/z: 482, [M]+. An NMR spectrum1H (DMSO-d6, δ, ppm, J/Hz): 1.9-2.1 (m, 2H, CH2), 2.42 (s, 6N, 2×CH3), 2.92 (s, 6N, 2×CH3), 3.0-3.1 (USM, 4H, 2×CH2), 3.71 (s, 6N, 2×CH3Oh), 6.63 (s, 2H, 2×CHarene). Found (percent): C, 62.64; H, 5.72; N, 5.22. C25H26N2O4S2. Calculated (%): C, 62.24; H, 5.39; N, 5.80.

1,2-bis(2-methyl-5-oximeter-4H-thieno[3,2-b]pyrrol-3-yl)cyclopentan 19

To a well stirred solution of compound 18 (12 mmol) in 5 ml of ether was added LiAlH4(10 mmol) and the reaction mixture was stirred for 1 hour. When cooled, added water, and the separated ether layer. The solvent was distilled, the resulting product was cleaned using flash chromatography on silica gel (Merck, 0.063-0.1), eluent - petroleum ether (40/70)-AcOEt (10:1, by vol.). Exit 19 (43%) with TPL 155-157 .5°C. Mass spectrum, m/z: 426, [M]+. An NMR spectrum1H (DMSO-d6, δ, ppm, J/Hz): 1.9-2.1 (m, 2H, CH2), 2.42 (s, 6N, 2×CH3), 2.92 (s, 6N, 2×CH3), 3.0-3.1 (USM, 4H, 2×CH2), 4.82 (s, 4H, 2×CH2), 6.61 (s, 2H, 2×CHarene). Found (percent): C, at 64.34; H, 6.32; N, 6.12. C23H26N2O2S2. Calculated (%): C, 64.79; H, 6.10; N, 6.57.

1,2-bis(2-methyl-5-formyl-4H-thieno[3,2-b]pyrrol-3-yl)cyclopentan 20

To a well stirred solution of compound 19 (12 mmol) in 20 ml of methylene chloride was added to the complex of chromium trioxide with two molecules of the mi pyridine (72 mmol) and the reaction mixture was stirred for 30 min at room temperature. The solvent was distilled, the resulting product was cleaned using flash chromatography on silica gel (Merck, 0.063-0.1), eluent - petroleum ether (40/70)-AcOEt (10:1, by vol.). Exit 20 (32%) as a viscous oil.

Mass spectrum, m/z: 422, [M]+. An NMR spectrum1H (DMSO-d6, δ, ppm, J/Hz): 1.9-2.0 (m, 2H, CH2), 2.40 (s, 6N, 2×CH3), 2.92 (s, 6N, 2×CH3), 3.0-3.1 (USM, 4H, 2×CH2), 6.58 (s, 2H, 2×CHarene.), 10.02 (USS, 2H SNO). Found (percent): C, 65.66; H, 7.62; N, 10.45. C23H22N2O2S2. Calculated (%): C, 65.40; H, 7.97; N, 10.14.

Example 4

Photochromic 1,2-bis(2-methyl-5-formestane[3,2-b]thiophene-3-yl)cyclopentan 25 of the class used photochromic monomers were synthesized according to the scheme shown in figure 10.

1,5-bis-(2-methyl-5-methoxycarbonyl-4H-thieno[3,2-b]thiophene-3-yl)pentane-1,5-dione 22

To a well stirred mixture of 20.2 mmol 2-methyl-5-methoxycarbonyl-4H-thieno[3,2-b]thiophene 21 and 10.1 mmol of dichlorohydrin glutaric acid in 50 ml of methylene chloride are added at 0°42.5 mmol of anhydrous aluminum chloride. The reaction mass is stirred at room temperature for 6 hours. Poured on ice water, extracted with methylene chloride (3×100 ml), the collected organic layers washed with aqueous solution of NaHCO3, dried over magnesium sulfate, the solvent evaporated under vacuum. The residue is recrystallized from hexane. Exit 22 (82), TPL 165-167°With (hexane; chloroform, 6:1, by vol.). Mass spectrum, m/z: 520, [M]+, An NMR spectrum1H (DMSO-d6, δ, ppm, J/Hz): 2.0-2.2 (m, 2H, CH2), 2.62 (s, 6N, 2×CH3), 3.1-3.2 (USM, 4H, 2×CH2), 3.82 (s, 6N, 2×CH3Oh), 6.84 (s, 2H, 2×CHareneFound (percent): C, 53.28; H, 3.65. With23H20About6S4. Calculated (%); C, 53.08; H, 3.87.

1,2-bis(2-methyl-5-methoxycarbonyl-4H-thieno[3,2-b]thiophene-3-yl)cyclopentan 23

To a well stirred suspension 7.93 mmol of zinc in fresh anhydrous THF (50 ml) at -10°With under argon is added dropwise 2.8 ml of TiCl4. After the addition, the reaction mixture is heated under argon for 1 h Cooled to 20°and add 12.8 mmol diketone 22 and anhydrous pyridine (5 ml). Boil under argon for another 20 hours Poured into 10% K2CO3(150 ml) and the aqueous layer was extracted with Et2O (5×100 ml). The collected organic extracts are dried MgSO4and distilled under vacuum. The residue is cleaned using flash chromatography on silica gel (Merck, 0.063-0.1), eluent - petroleum ether (40/70)-AcOEt (10:1, by vol.). Exit 23 (60%) with TPL 177.5-176.5°C. Mass spectrum, m/z: 488, [M]+. An NMR spectrum1H (DMSO-d6, δ, ppm, J/Hz): 1.9-2.1 (m, 2H, CH2), 2.42 (s, 6N, 2×CH3), 3.0-3.1 (USM, 4H, 2×CH2), 3.71 (s, 6N, 2×CH3Oh), 6.63 (s, 2H, 2×CHarene). Found (percent): C, 56.83; H, 4.22. With23H20O4S4. Calculated (%): the, At 56.55; H, 4.10.

1,2-bis(2-methyl-5-oximeter-4H-thieno[3,2-b]thiophene-3-yl)cyclopentan 24

To a well stirred solution of compound 23 (12 mmol) in 5 ml of ether was added LiAlH4(10 mmol) and the reaction mixture was stirred for 1 hour. When cooled, added water, and the separated ether layer. The solvent was distilled, the resulting product was cleaned using flash chromatography on silica gel (Merck, 0.063-0.1), eluent - petroleum ether (40/70)-AcOEt (10:1, by vol.). Exit 24 (59%) as a viscous oil. Mass spectrum, m/z: 432, [M]+. An NMR spectrum1H (DMSO-d6, δ, ppm, J/Hz): 1.9-2.1 (m, 2H, CH2), 2.42 (s, 6N, 2×CH3), 3.0-3.1 (USM, 4H, 2×CH2), 4.82 (s, 4H, 2×CH2), 6.61 (s, 2H, 2×CHarene). Found (percent): C, 63.34; H, 4.52. C21H20O2S4. Calculated (%): C, 63.89; H, 4.63.

1,2-bis(2-methyl-5-formyl-4H-thieno[3,2-b]thiophene-3-yl)cyclopentan 25

To a well stirred solution of compound 24 (12 mmol) in 20 ml of methylene chloride was added to the complex of chromium trioxide with two molecules of pyridine (72 mmol) and the reaction mixture was stirred for 30 min at room temperature. The solvent was distilled, the resulting product was cleaned using flash chromatography on silica gel (Merck, 0.063-0.1), eluent - petroleum ether (40/70)-AcOEt (10:1, by vol.). Exit 25 (28%) as a viscous oil. Mass spectrum, m/z: 428, [M]+. An NMR spectrum1H (DMSO-d6, δ, ppm, J/Hz): 1.9-2.1 (m, 2H, CH 2), 2.42 (s, 6N, 2×CH3), 3.0-3.1 (USM, 4H, 2×CH2), 4.82 (s, 4H, 2×CH2), 6.61(s, 2H, 2×CHarene), 9.11 (USS, 2H, Cho). Found (%); C, at 64.34; H, 3.62. With21H16S4. Calculated (%): C, 64.49; H, 3.74.

Example 5

Photochromic 1,2-bis(3,5-dimethyl-2-formestane[3,2-b]furan-6-yl)cyclopentan 31 of the class used photochromic monomers were synthesized according to the scheme shown in 11.

Ethyl 3,5-dimethylthieno[3,2-b]furan-2-carboxylate 27

3 Hydroaxe-5-methylthiophene 26 was obtained from 2-methyl-4-bromo-thiophene according to the method described in Organic Syntheses, Coll. Vol.5, p.642 (1973); Vol.43, p.55 (1963). To a solution of hydroxythiophene 18 (1.5 mmol) in 5 ml of benzene was added 1 mmol of NaH and heated to the boiling point of the reaction mixture were added 1.5 mmole of ethylchlorothioformate. The mixture is boiled for 4 hours and cooled, washed with water, the organic layer was dried over MgSO4. The solvent was distilled, the resulting substance was added with stirring for 1 h to 3 ml of concentrated sulfuric acid at a temperature of 5°C. the Mixture was stirred for another 1 h and Then added a mixture of water and ice and was extracted with 2 times 5 ml of benzene. The organic layer was washed with water, sodium carbonate solution, dried over MgSO4and removed, the product was isolated on a column of silica gel (eluent CHCl3). Exit 27 (48%), TPL 120-121°C. Mass spectrum, m/z: 224, [M]+. An NMR spectrum1H (DMSO-d6, δ, M.D.); 1.31 (m, 3H, CH3), 1.93 (s, 3H, CH3), 2.43 (s, 3H, CH3), 4.31 (m, 2H, CH2), 6.76 (s, N, Harene). Found (%); C, 58.83; H, 5.22; S, 14,18. With11H12About3S. Calculated (%): C, 58.91; H, 5.39; S, 14.30.

1,5-bis(3,5-dimethyl-2-ethoxycarbonylethyl[3,2-b]furan-6-yl)pentane-1,5-dione 28

To a well stirred mixture of 20.2 mmol of taeniura 27 and 10.1 mmol of dichlorohydrin glutaric acid in 50 ml of methylene chloride are added at 0°42.5 mmol of anhydrous aluminum chloride. The reaction mass is stirred at room temperature for 6 hours. Poured on ice water, extracted with methylene chloride (3×100 ml), the collected organic layers washed with aqueous solution of NaHCO3, dried over magnesium sulfate, the solvent evaporated under vacuum. The residue is recrystallized from hexane. Exit 28 (82%), TPL 169-170°With (hexane: chloroform, 6:1, by vol.). Mass spectrum, m/z: 544, [M]+. An NMR spectrum1H (DMSO-d6, δ, ppm): 1.34 (m 6N, 2×CH3), 1.96 (m, 2H, CH2), 1.98 (s, 6N, 2×CH3), 2.40 (m, 4H, 2×CH2), 2.43 (s, 6N, 2×CH3), 4.31 (m, 4H, 2×CH2). Found (percent): C, 59.64; H, 5.22; S, 11.82. With27H28O8S2. Calculated (%): C, 59.54; H, 5.18; S, 11.77.

1,2-bis(3,5-dimethyl-2-ethoxycarbonylethyl[3,2-b]furan-6-yl)cyclopentan 29

To a well stirred suspension 7.93 mmol of zinc in fresh anhydrous THF (50 ml) at -10°under ergonomically dropwise 2.8 ml of TiCl 4. After the addition, the reaction mixture is heated under argon for 1 h Cooled to 20°and add 12.8 mmol diketone 28 and anhydrous pyridine (5 ml). Boil under argon for another 20 hours Poured into 10% K2CO3(150 ml) and the aqueous layer was extracted with Et2O (5×100 ml). The collected organic extracts are dried MgSO4and distilled under vacuum. The residue is cleaned using flash chromatography on silica gel (Merck, 0.063-0.1), eluent - petroleum ether (40/70)-AcOEt (10:1, by vol.). Exit 29 (62%) with TPL 198.5-199.5°C. Mass spectrum, m/z 512, [M]+. An NMR spectrum1H (DMSO-d6, δ, ppm): 1.34 (m 6N, 2×CH3), 1.94 (m, 2H, CH2), 1.98 (s, 6N, 2×CH3), 2.31 (m, 4H, 2×CH2), 2.40 (m, 4H, 2×CH2), 2.42 (s, 6N, 2×CH3). Found (percent): C, 63.34; H, 5.62; N, 12.36. With27H28O6S2. Calculated (%): C, 63.26; H, 5.51; S, 12.51.

1,2-bis(3,5-dimethyl-2-oxymethylene[3,2-b]furan-6-yl)cyclopentan 30

To a well stirred solution of compound 29 (12 mmol) in 5 ml of ether was added LiAlH4(10 mmol) and the reaction mixture was stirred for 1 hour. When cooled, added water, and the separated ether layer. The solvent was distilled, the resulting product was cleaned using flash chromatography on silica gel (Merck, 0.063-0.1), eluent - petroleum ether (40/70)-AcOEt (10:1, by vol.). Exit 30 (59%) with TPL 168.5-169.5°C. Mass spectrum, m/z 428, [M]+. An NMR spectrum1H (DMSO-d6, δ, ppm): 1.94 (who, 2H, CH2), 1.98 (s, 6N, 2×CH3), 2.31 (m, 4H, 2×CH2), 2.42 (s, 6N, 2×CH3) 4.62 (s, 4H, 2×CH2). Found (percent): C, at 64.34; H, 5.52. With23H24O4S2. Calculated (%): C, 64.48; H, 5.64; S, 14.96.

1,2-bis(3,5-dimethyl-2-formestane[3,2-b]furan-6-yl)cyclopentan 31

To a well stirred solution of compound 30 (12 mmol) in 20 ml of methylene chloride was added to the complex of chromium trioxide with two molecules of pyridine (72 mmol) and the reaction mixture was stirred for 30 min at room temperature. The solvent was distilled, the resulting product was cleaned using flash chromatography on silica gel (Merck, 0.063-0.1), eluent - petroleum ether (40/70)-AcOEt (10:1, by vol.). Exit 31 (28%) as a viscous oil. Mass spectrum, m/z: 424, [M]+. An NMR spectrum1H (DMSO-d6, δ, ppm, J/Hz): 1.9-2.1 (m, 2H, CH2), 2.42 (s, 6N, 2×CH3), 3.0-3.1 (USM, 4H, 2×CH2), 4.82 (s, 4H, 2×CH2), 6.78 (s, 2H, 2×CHarene), 9.34 (USS, 2H, Cho). Found (percent): C, 65.24; H, 4.56. With23H20O4S2. Calculated (%); C, 65.09; H, 4.72.

Example 6

Synthesis polyazomethine III was carried out from 1,2-bis(2-methyl-6-formyl-1-benzothiophen-3-yl)cyclopentane (compound 5A) and benzidine according to the scheme shown in Fig. In a three-neck flask with a capacity of 25 ml and equipped with a stirrer, reflux condenser and input for argon, place 0.25 g (0.6 mmol) of 1,2-bis(2-methyl-6-formyl-1-benzothiophen the-3-yl)cyclopentane (compound 5A) 0,110 g (0.6 mmol) of benzidine (II), 1 ml of N-methylpyrrolidone, hexamethylphosphoramide and 0,047 g dry LiCl. The solution is stirred for 16 hours at room temperature, then the reaction mixture was poured into methanol, the precipitate is washed with water, then with methanol and the polymer is dried under vacuum for 24 hours at t=60°C.

The yield of polymer III 97%. X (KBr, cm-1): C=N 1680. Mn=35000. The polymer is soluble in chloroform, tetrahydrofuran (THF), when heated in dimethylformamide (DMF) and toluene, insoluble in ethanol and acetone.

Sample photochromic polymer for measuring the spectral-kinetic characteristics were prepared by co-dissolving the photochromic polymer and polycarbonate, which was used as a polymeric binder, in chloroform. Then the solution was applied on a quartz substrate by centrifuging. The result was obtained photochromic film, which were measured by the method of example 1 absorption spectra of form a (Fig, curve 1) and form (Fig, curve 2), and kinetic curves photocreative (Fig, curve 1) and photobleaching (Fig, curve 2). In favor of the reversibility of the photochromic transformations evidenced by the reduction of photoinduced optical density under the action of visible light (Fig, curve 3). The spectral and kinetic data indicate photochrom is the PCA samples photochromic film.

Example 7

Polyazomethine IIIa (Fig) were obtained from the photochromic monomer I and 3,3'-diaminodiphenyl analogously to example 6. Yield 92%. Mn=28000. The polymer is soluble in chloroform, tetrahydrofuran, dimethylformamide and toluene, insoluble in ethanol and acetone.

Spectral-kinetic characteristics measured by the method described in example 1 for sample photochromic polymer made according to methods described in example 5 indicate practically acceptable photochromism of this polymer.

Example 8

Polyazomethine IIIb (Fig) were obtained from the photochromic monomer I and 4,4'-diaminoazobenzene analogously to example 6. Yield 95%. Mn=26000. The polymer is soluble in chloroform, tetrahydrofuran, dimethylformamide, not soluble in toluene, ethanol and acetone.

Spectral-kinetic characteristics measured by the method described in example 1 for sample photochromic polymer made according to methods described in example 5 indicate practically acceptable photochromism of this polymer.

Example 9

Polyazomethine IIIc (Fig) were obtained from the photochromic monomer I and 4,4'-diaminodiphenylmethane analogously to example 6. Output 90%. Mn=31000. The polymer is soluble in chloroform, tetrahydrofuran, dimethylformamide, not soluble in toluene, ethanol and acetone.

Spectral-kinetic characteristics, measured m is Todd, described in example 1 for sample photochromic polymer made according to methods described in example 2 indicate practically acceptable photochromism of this polymer.

Example 10

Polyazomethine IIId (Fig) were obtained from the photochromic monomer I and 2-(p-AMINOPHENYL)-5(6)-aminobenzimidazole analogously to example 6. Exit 98%. Mn=38000. The polymer is soluble in dimethylformamide, is not soluble in chloroform, tetrahydrofuran, toluene, ethanol and acetone.

Spectral-kinetic characteristics measured by the method described in example 1 for sample photochromic polymer made by the method shown in example 6, indicate practically acceptable photochromism of this polymer.

Example 11

Synthesis of Cardo polyazomethine V of the photochromic monomer I and anyoption IV was carried out according to the scheme shown in Fig. Polymer V based compounds 5A and anyoption IV obtained similarly polyazomethine III according to example 6. Yield 96%. IR (KBr, cm-1): C=N 1680. Mn=30000. The polymer is soluble in chloroform, tetrahydrofuran, dimethylformamide, and when heated in toluene, insoluble in ethanol and acetone.

Sample photochromic polymer for the spectral-kinetic studies were made by the method described in example 5.

Spectral and kinetic measurements were carried out according to the method is written in example 6. The obtained absorption spectra of the initial and photoinduced forms (Fig) and kinetic curves photocreative and photobleaching (Fig) indicate acceptable photochromism samples photochromic film.

Example 12

Cardo polymer Va (Fig) on the basis of the photochromic monomer I and anyinflate obtained similarly polyazomethine V. the Output is 92%. Mn=32000. The polymer is soluble in chloroform, tetrahydrofuran, dimethylformamide, not soluble in toluene, ethanol and acetone.

Spectral-kinetic characteristics measured by the method described in example 1 for sample photochromic polymer made by the method shown in example 6, indicate practically acceptable photochromism of this polymer.

Example 13

Polyazomethine VI (Fig) were obtained from the photochromic monomer 17 and 3,3'-diaminodiphenyl analogously to example 6. Yield 92%. Mn=28000. The polymer is soluble in chloroform, tetrahydrofuran, dimethylformamide and toluene, insoluble in ethanol and acetone.

Spectral-kinetic characteristics measured by the method described in example 1 for sample photochromic polymer made by the method shown in example 6, indicate practically acceptable photochromism of this polymer.

Example 14

Polyazomethine VII (Fig) were obtained from the photochromic monomer 25 and 3'-diaminodiphenyl analogously to example 6. Yield 92%. Mn=30000. The polymer is soluble in chloroform, tetrahydrofuran, dimethylformamide and toluene, insoluble in ethanol and acetone.

Spectral-kinetic characteristics measured by the method described in example 1 for sample photochromic polymer made by the method shown in example 6, indicate practically acceptable photochromism of this polymer.

Example 15

Polyazomethine VIII (Fig) were obtained from the photochromic monomer 31 and 3,3'-diaminodiphenyl analogously to example 6. Yield 92%. Mn=26000. The polymer is soluble in chloroform, tetrahydrofuran, dimethylformamide and toluene, insoluble in ethanol and acetone.

Spectral-kinetic characteristics measured by the method described in example 1 for sample photochromic polymer made by the method shown in example 6, indicate practically acceptable photochromism of this polymer.

1. Photochromic monomers of General formula

Alk=CH3-C10H21

X=Cl, Br, I, F, NH2CH2HE, CH2Cl, CH2Br, CHO, CO2N.

2. A method of obtaining a photochromic monomers according to claim 1, comprising the acylation derivatives baie is stiofan, percolation, thienothiophene, pornotopia dichlorohydrin glutaric acid in methylene chloride in the presence of aluminum chloride and subsequent reductive cyclization of the obtained diketones under the action of TiCL4, Zn in tetrahydrofuran (THF) in the presence of pyridine, with further formirovanie reaction products dichlormethane ether in nitrobenzene in the presence of aluminum chloride.

3. Photochromic polyazomethine based photochromic monomers according to claim 1, having a molecular weight of from 25,000 to 50,000 and General structural formula:

where Alk=CH3-C10H21

y=-C=N-; -N=C-

where n=50-100.

4. A method of obtaining a photochromic polyazomethines according to claim 3, comprising the polycondensation in solution of the monomer according to claim 1 with a diamine or a dialdehyde at a temperature of from about 20 to 200°C.

5. Photochromic Cardo polyazomethine based photochromic monomers according to claim 1, having a molecular weight of from 30,000 to 50,000 and General structural formula:

where Alk=CH3-C10H21

y=-C=N-; -N=C-

where n=50-100.

6. The method of obtaining Cardo photochromic polyazomethines according to claim 5, comprising the polycondensation in solution photochromic monomers according to claim 1 with aromatic Cardo diamines or dialdehyde at a temperature of about 20-200°C.

7. The use of photochromic polyazomethines according to claim 3 in Photonics devices.

8. The use of photochromic Cardo polyazomethines according to claim 5 devices in Photonics, especially in photobrowser displays, as well as three-dimensional optical random-access memory, linear and nonlinear optical photoperiodically radiation.



 

Same patents:

FIELD: chemistry.

SUBSTANCE: present invention pertains to new photochromic monomers and new polymers based on such monomers, intended for use in making two-photon photochromic recording media for three dimensional optical memory and photoswitches of optical signals. Description is given of monomers

Q=; ; ;

Alk=CH3-C10H21 X=Cl, Br, I, F, NH2, CH2OH, CH2Cl, CH2Br, CHO, CO2H and X=CH2, O, S, NAlk; Y=O, S, NAlk; n=0-6; Q=; ; ; ; ;

Alk=CH3-C10H21, methods of obtaining them, photochromic polymers based on them, method of obtaining photochromic monomers and their application. The proposed materials exhibit thermal irreversibility of photochromic transformations and properties, making it possible to use photochromic polymers in two-photon random access optical memory.

EFFECT: obtaining materials with thermal irreversibility of photochromic transformations and properties, making it possible to use photochromic polymers in two-photon random access optical memory.

15 cl, 46 dwg, 31 ex

FIELD: information technologies.

SUBSTANCE: invention refers to information medium, to record and reproduction modes and devices. Information medium includes record material "L-H" ("low to high"). And record wavelength is shorter than 620 nanometers. Channel bit length is less than 105 nm. Track pitch is shorter than 600 nm. Minimum number of series channel bits of value "0" after modulation is equal 1.

EFFECT: elimination of substrate and record sensitivity deformation.

5 cl, 128 dwg

FIELD: information technologies.

SUBSTANCE: invention refers to recording technology applying high recording density optical disks, specifically of single record disks of BD-WO standard. According to invention record medium supplied with data structure for record medium data area control, contains defect control area storing the first data block storing the first information including data area record state; the second information including defect list, and the third information including the first indication specifying address where the first information is recorded.

EFFECT: available effective and advanced application of single record carrier, such as disk of BD-WO standard.

12 cl, 7 dwg

FIELD: chemistry.

SUBSTANCE: composition for coating of optical transparent information carriers is described, the composition being curable by UV radiation and including (A) from 1 to 60% by mass of at least one colloid oxide of metal, (B) from 0.1 to 50% by mass of at least one silyl acrylate hydrolysis product having a general formula (I): , (I) where a means an integer from 0 to 2, b means an integer from 1 to 3, and the sum a+b is from 1 to 3, R independently means non-branched or branched alkyl residue with 1 to 8 carbon atoms, cycloalkyl residue with 3 to 8 carbon atoms, unsubstituted or substituted aryl residue with 6 to 10 carbon atoms in the aryl portion, R1 independently means hydrogen, non-branched or branched alkyl residue with 1 to 8 carbon atoms, cycloalkyl residue with 3 to 8 carbon atoms, unsubstituted or substituted aryl residue with 6 to 10 carbon atoms in the aryl portion, R2 independently means hydrogen, non-branched or branched alkyl residue with 1 to 8 carbon atoms, unsubstituted or substituted aryl residue with 6 to 10 carbon atoms, R3 means single bond, or non-branched or branched, if necessary, substituted alkylene residue (alkane dienyl residue) with 1 to 8 carbon atoms in alkylene residue, or, if necessary, substituted arylene residue (aryl dienyl residue) with 6 to 10 carbon atoms in arylene residue, (C) from 25 to 90% by mass of at least one acrylate monomer of general formula (II) where n means a number from 1 to 6, R4 means hydrogen, non-branched or branched alkyl residue with 1 to 8 carbon atoms, unsubstituted or substituted aryl residue with 6 to 10 carbon atoms in the aryl portion and where substituents R4 may be the same or different; R5 means unsubstituted or substituted organic residue having a valency from 1 to 6 such as, if necessary, substituted, non-branched or branched aliphatic or aromatic hydrocarbon residue with 1 to 20 carbon atoms, and (D) from 0.01 to 15% by mass of at least one UV photoinitiator, respectively, with respect to the total mass of the composition, the composition being intended for coating transparent, polycarbonate-based, optical information carriers.

EFFECT: proposed composition is scratch-resistant and highly adhesive to the substrate surface.

3 cl, 2 tbl, 4 ex

FIELD: lighting.

SUBSTANCE: multilayer record carrier of a writable type has a first recording layer (40) having a first recording stack (50, 51) of a first type and a second recording layer (41) having a second recording stack (54, 55) of a second type. The first and second recording stacks have different writing parameters. Each recording layer has a pre-formed recording control pattern that is readable via a laser beam for indicating the track. At least one recording control pattern comprises recording stack type indicator for indicating the writing parameters of the second recording stack. A recording device has a control unit (20) for adjusting recording parameters in the device in dependence of the recording stack type indicator retrieved from the recording control pattern.

EFFECT: creation of the multilayer optical disc.

8 cl, 7 dwg

FIELD: personal computer hardware, possible use as information storage in computers, audio and video equipment.

SUBSTANCE: effect is achieved by reading and recording information on an immobile disk. Information storage, containing laser emitter, objective, impulse amplifier, buffer memory block and two-sided one-layered disk, additionally features block of sinusoidal oscillations and block for shifting phase for 90°, two amplifiers and two piezo-deflectors with reflectors on end, encoder and decoder, and a layer of photo-receiver is introduced into optical disk between first and second recording layers.

EFFECT: exclusion of disk drive and automatic tracking and regulating systems from composition of information storage.

6 dwg

Film compact-disk // 2313835

FIELD: engineering of optical record carriers.

SUBSTANCE: film compact-disk includes registering, reflecting, main and protective layers. Minimization of total thickness of compact-disk film is achieved by discontinuous enclosures of magnetic material, positioned in such a way, that in magnetic field magnetic material not only promotes setting of disk in given position, but also promotes rotation of the disk in its plane, with thickened parts on disk planes, positioned from the center towards the edge of circle in such a way, that air is captured during rotation of disk and forced out by centrifugal forces. The aperture in the middle of the disk is used for influx of air for cooling the disk.

EFFECT: increased efficiency.

5 dwg

FIELD: improved multi-bit magnetic memorizing device with arbitrary selection and methods for functioning and manufacture of such a device.

SUBSTANCE: magnetic memory includes one or more paired cells, each one of which has multilayer magnetic structure. Structure contains magnetic-changeable ferromagnetic layer, ferromagnetic basic layer, having non-changeable magnetization state, and corresponding separating layer which divides ferromagnetic layers. Memory cells are ordered in such a way, that effective remaining magnetization of each cell is not parallel to cell axis which is parallel to its long side. Methods describe functioning process of such a device.

EFFECT: increased data recording density, reduced energy consumption and simplified manufacturing process of memorizing device.

3 cl, 30 dwg

FIELD: optical information recording, possible use for creating holographic optical elements.

SUBSTANCE: in accordance to method for recording information on amorphous chalcogenide film, including effect of laser radiation with energy exceeding width of forbidden zone, film is used based on germanium and gallium chalcogenides, which is produced by means of impulse laser spraying method.

EFFECT: production of high contrast information recording, increased resolution, cheaper information recording process.

3 cl, 4 dwg

FIELD: multi-layered body and method for producing multi-layered image in such a multi-layered body.

SUBSTANCE: multi-layered body contains two layers sensitive to laser radiation with partial overlapping. First and second laser radiation sensitive layers contain colorant, which under effect of laser radiation loses color or under effect of laser radiation changes its color, or laser radiation sensitive layer contains alloyed material, which under effect of laser radiation is subject to blackening. In first layer sensitive to laser radiation a multi-layered laser-induced component part of image may be formed, while in second laser radiation sensitive layer black marking may be formed, preferably a grayscale image, and/or special background layer at sections is located as intermediate layer between laser radiation sensitive layers and acts as locking layer, which is not transparent for laser radiation. In accordance to method of forming of multi-layered image in multi-layered body, multi-layered image is composed of several laser-induced components of image.

EFFECT: creation of multi-layered body, which realizes high degree of protection from forgery and special marking induced by laser.

2 cl, 7 dwg

FIELD: chemistry.

SUBSTANCE: present invention pertains to new photochromic monomers and new polymers based on such monomers, intended for use in making two-photon photochromic recording media for three dimensional optical memory and photoswitches of optical signals. Description is given of monomers

Q=; ; ;

Alk=CH3-C10H21 X=Cl, Br, I, F, NH2, CH2OH, CH2Cl, CH2Br, CHO, CO2H and X=CH2, O, S, NAlk; Y=O, S, NAlk; n=0-6; Q=; ; ; ; ;

Alk=CH3-C10H21, methods of obtaining them, photochromic polymers based on them, method of obtaining photochromic monomers and their application. The proposed materials exhibit thermal irreversibility of photochromic transformations and properties, making it possible to use photochromic polymers in two-photon random access optical memory.

EFFECT: obtaining materials with thermal irreversibility of photochromic transformations and properties, making it possible to use photochromic polymers in two-photon random access optical memory.

15 cl, 46 dwg, 31 ex

FIELD: technological processes.

SUBSTANCE: method of object protection against forgery includes application of information identifying mark to the surface of protected object by means of glue layer, in composition of which light-sensitive protein bacteriorhodopsin is introduced. Information identifying mark or its part is made transparent, and corresponding portion of protected object surface is made transparent or with mirror reflecting coating. During monitoring of object authenticity light-sensitive element that contains bacteriorhodopsin is illuminated, by means of two sources of light with lengths of waves, accordingly, in band of main and intermediate conditions of bacteriorhodopsin absorption.

EFFECT: invention allows to increase reliability of protection against forgery and monitoring of valuable documents and items.

3 cl, 4 dwg

FIELD: physics, photographic material.

SUBSTANCE: invention pertains to polymer cholesteric photoactive compounds, which can independently generate laser emission when irradiated with laser light. Such a compound can be used, for example, in photonics, optoelectronics and telecommunication systems. The cholesteric photoactive compound for generating laser emission consists of cholesteric liquid crystal, photoactive additive and laser dye. The liquid crystal used contains conjoint polymer n-(6-acrylyl oxycapril hydroxyphenyl)-n-methoxy benzoate with cholesterine-11-acrylyl undecanoate, containing molar quantities between 30% and 25% of the cholesterine-11-acrylyl undecanoate links. Photoactive additive used is 2.5-bis(4-methoxy cynnamoyl)-1.4;3.6-dianhydro-B-sorbitol, while the laser dye used is 4-(dicyano methylene)-2-methyl-6-(4-dimethyl amino styryl)-4H-pyran. The invention improves the temporal and thermal stability of the compound, and allows for its use at room temperatures and at lower temperatures as well. Sensitivity of the compound to external effects is also lowered.

EFFECT: increased thermal stability of photoactive compounds and lower sensitivity to external effects.

2 ex, 1 dwg

FIELD: polymer materials.

SUBSTANCE: invention relates to technology of manufacturing transparent profiled articles, for example, containers and bottles. Transparent article comprises continuous polyester matrix containing at least one incompatible filler dispersed therein. Incompatible filler provides domains in polyester matrix, each of them having particular size thereby forming a size range for domains contained in an article. To create turbidity, domain sizes lie within the range between about 400 nm and about 700 nm. Once size range is determined, a light absorbing substance can be selected to absorb light within a wavelength range, which at least essentially overlaps the preliminarily found domain size range.

EFFECT: facilitated finding substance masking turbidity of a polymer article.

20 cl, 12 dwg, 3 tbl

FIELD: organic chemistry, chemical technology.

SUBSTANCE: invention relates to novel oxazine compounds of the formula (I): wherein X means carbon atom; R1 and R2 mean hydrogen atom; n = 0; A and A' mean independently of one another: (a) linear or branched (C1-C12)-alkyl, (C3-C12)-cycloalkyl; (b) unsubstituted or monosubstituted aryl groups. Also, invention relates to a method for synthesis of photochrome oxazine compounds of the formula (I). Invention provides synthesis of novel compounds and a method for their synthesis used as photochrome compounds.

EFFECT: improved method of synthesis.

10 cl, 1 tbl, 9 ex

FIELD: optical materials.

SUBSTANCE: invention relates to radiation-sensitive compositions with variable refraction coefficients allowing novel model with refraction coefficient distribution to be obtained, in particular optical material used in optical electronics and information representation devices. Invention discloses emission-sensitive composition with variable dielectric permittivity containing decomposable compound (A), non-decomposable component (B) including inorganic oxide particles resistant to acid or base originated from acid or base source (C), and radiation-sensitive degradable substance (C), wherein refraction coefficient nA of decomposable compound A and refraction coefficient nB of non-decomposable compound B lie in one of following relationships: nB-nA ≥ 0.05 (1) and nA-nB ≥ 0.05 (2), amount of component B ranges from 10 to 90 wt parts based on 100 wt parts of summary amount of components A and B, and amount of component C ranges from 0.01 to 30 wt parts based on 100 wt parts of summary amount of components A and B. Model obtained from indicated composition allows one to vary in a simple way refraction coefficients thereby achieving sufficiently large difference between them and their stability irrespective of application conditions.

EFFECT: expanded possibilities in optical representation of information.

12 cl, 3 tbl, 7 ex

FIELD: optical data carriers.

SUBSTANCE: device has cation dye or mixture of cation dyes with optical characteristics, changed by means of recording beam, an at least one substance with functions of damper and phenol or substituted phenol with one hydroxide group or more, while it additionally contains phenol or substituted phenol in form of phenolate ion, forming a portion of anions for dye cations, as a stabilizer. Data carrier can contain anionic metal-organic thyolene complex as damper, which forms other portion of anions for dye cations.

EFFECT: higher stability, higher durability, lower costs.

5 cl, 1 tbl, 3 ex

FIELD: color-forming compositions and recording material.

SUBSTANCE: claimed composition includes developer containing urea-urethane compound and colorless or light colored leuco dye. Recording material based on this composition also is proposed.

EFFECT: color-forming compositions with improved image conservation ability and increased image intensity.

21 cl, 14 tbl, 153 ex

The invention relates to a method for ensuring the authenticity of the subject by applying to a photochromic ink

The invention relates to the field of devices that change color under the influence of electric current, namely, the electrochromic device and method of its manufacture

FIELD: nonferrous metallurgy industry; aircraft industry; other industries; production of the heat-resistant alloys on the basis of the nickel.

SUBSTANCE: the invention is pertaining to the dispergated coloring agents intended for the ink-jet recording. The invention describes the dispergated coloring agent containing the coloring agent and the pseudo-finely-dispergated particles of the polarizable polymer having the dimension less, than the particles of the coloring agent. In the dispergated coloring agent the coloring agent itself and the particles of the polarizable polymer are attached to each other. At that the pseudo-finely-dispergated particles of the polarizable polymer contain the interpolymer consisting of the monomeric components containing, at least, one type of the hydrophobic monomer and, at least, one type of the hydrophilic monomer, where the hydrophobic monomer contains, at least, the monomer having the methyl group in α - position and the radically-polymerizable non-saturated double bond. The invention also describes the method of production of the indicated dispergated coloring agent and the water ink produced on its basis. The presented dispergated coloring agent has the high stability for a long time and practically in the absence of the surface-active substance or the dispergator. The ink produced on its basis has stability of blowout in the ink-jet printing method.

EFFECT: the invention ensures, that the ink produced on the basis of the presented dispergated coloring agent has the high stability of blowout in the ink-jet printing method.

20 cl, 14 dwg, 7 tbl, 15 ex

Up!