PL212902B1 - Colourful imidazol salts and production method of colourful imidazol salts - Google Patents

Description

Description of the invention

The present invention relates to colored imidazolium salts and a method for preparing colored imidazolium salts.

Imidazolium salts are organic compounds consisting of an organic cation containing an imidazole ring with a positive charge on the azomethine nitrogen atom, stabilized by a negative ion, derived from an anion, of an inorganic or organic nature. The area of application of imidazolium salts increases from year to year. This is due to the unique properties of this group of compounds. They show high surface activity, are effective in destroying bacteria and fungi, have antistatic and anti-caking properties. They have also found application in catalysis as phase transfer catalysts, in electroplating processes and in drug production.

Eosin is a bromo derivative of fluorescein and is present as red crystals. It is soluble in alcohol, and its sodium and potassium salts are soluble in water, ethyl acetate and alcohol. Eosin is used as a dye for textiles, in the production of ink, in the coloring of cosmetics and gasoline, and as a component of toners. Eosin salts. sodium or potassium, they are a red to pink crystalline powder. They are used in biology for staining cells: they stain acidic particles of cell structures such as cytoplasm. collagen fibers or most of the secretory grains in cells. Eosin is also strongly absorbed by red blood cells, staining them bright red.

Eosin B or its disodium salt has a distinctly bluish tinge, while Eosin Y or its disodium salt has a distinctly yellowish tinge. These compounds are soluble in water.

Fluorescein is a popular fluochromatic dye. It comes in the form of a yellowish to red crystalline powder. It is sparingly soluble in water, but dissolves well in dilute acids and bases. Fluoresceine is produced by the condensation of phthalic anhydride with resorcinol. It is the raw material for obtaining eosins. Fluorescein is used in dyeing silk and wool. Its sodium salt, also called uranine. it is used for dyeing textiles, in oceanography as a marker of sea water and in the dyeing of agrochemicals. detergents or antifreeze. Uranine is an orange-red crystalline powder, soluble in water, odorless.

Erythrosin B is the iodine derivative of fluorescein with a clearly bluish tinge. It is used to color cosmetics and food (11127). Erythrosine is also used as a dye for nerve cells and bacteria in the soil. This compound allows one to perceive the rotational diffusion of membrane proteins, acting as a phosphorescent probe.

₁

The invention relates to colored imidazolium salts of the general formula I. wherein R ¹ is a proton or bromine, or iodine or a nitro group, R ² is a proton or bromine, or iodine, R ³ is a proton or bromine, or iodine, ⁴ proton or bromine, or iodine, or nitro group, R ⁵ is a straight chain alkyl group containing from 2 to 12 carbon atoms and a process for the preparation of colored imidolol salts of general formula I in which R ¹ is proton or bromine, or iodine, or a nitro group, ^R2 is a proton or bromine or iodine, R ³ is a proton or bromine, Iub iodine, R ⁴ is a proton or bromine ₅

IUB iodine, Iub nitro, R ⁵ is a straight chain alkyl group containing from 2 to 12 ATO ₅ atoms, which is characterized in that the halides imidazolium general formula 2 wherein R ⁵ is a straight chain alkyl group containing from 2 to 12 carbon react with an organic salt of general formula 3, wherein R ¹ is a proton or bromine, or iodine, or a nitro group, R ² is a proton or bromine, or iodine, R ³ is a proton or bromine, or iodine, R ⁴ is proton or bromine, or iodine, or nitro group, M is potassium or sodium or ammonium cation, in a molar ratio of 2: 1 at a temperature of 277 K to 373 K in an aqueous medium, then the solvent is evaporated under reduced pressure at a temperature from 293 K to 333 K, an anhydrous organic solvent is added, then the precipitate is separated by filtration, acetone is evaporated and dried under reduced pressure at a temperature of 303 to 373 K.

₁

A second method for producing colored salts of imidazolium general formula 1, wherein R ¹ 23 is a proton or bromine, Iub iodine, Iub nitro, R ² is a proton or bromine, Iub iodine, R ³ is 45 proton or bromine, Iub iodine, R ⁴ is a proton or bromine, Iub iodine, Iub nitro, R ⁵ is prostołańcychową alkyl group containing from 2 to 12 carbon atoms, lies in the fact that halides imidazole ₅ zoliowe of general formula 2 wherein R ⁵ is a straight chain alkyl group having 2 from ₁ to 12 carbon atoms is reacted with an organic salt of general formula 3 wherein R ¹ is

GB 212 902 B1 proton or bromine, Iub iodine, Iub nitro, R ² is a proton or bromine, Iub iodine, R ³ is a proton or bromine, Iub iodine, R ⁴ is a proton or bromine, Iub iodine, Iub nitro, M denotes potassium or sodium, or ammonium, in a 2: 1 molar ratio at a temperature of 277 to 373K in an aqueous medium, then a hydrophobic organic solvent is added, then the organic layer is rinsed with distilled water until the disappearance of halogen ions in the effluent, further evaporation solvent under reduced pressure at a temperature above 293K. and dried in conditions of reduced pressure at a temperature above 293K.

Due to the solution according to the invention, the following technical and economic effects were obtained: new compounds belonging to the group of imidazolium salts were obtained.

The application use of these imidazolium salts is very wide, including:

- components of varnishes, paints, polymer-type coating materials (PHT, PP, PE, PVC),

- reaction catalysts,

- solvents,

- ingredients of wood preservatives against fungi and bacteria.

₁

Invention are colored imidazolium salts of formula 1 wherein R ¹ is a proton 23 or bromine, Iub iodine, Iub nitro, R ² is a proton or bromine, Iub iodine, R ³ is a proton or 45 bromine, Iub iodine, R ⁴ R5 represents a proton or bromine, or iodine, or a nitro group, R ⁵ is a straight chain alkyl group containing from 2 to 12 carbon atoms. The method of their preparation is illustrated by the following examples:

P r z k ł a d I

3-B-estoxymethyl-1-methylimidazolyl eosinate B ₃

0.005 moles of the sodium salt of eosin B were dissolved in 30 cm ³ of distilled water and _{3 were} introduced into a 100 cm ³ round-bottom flask equipped with a magnetic stirrer. 0.01 l mole of 3-butoxymethyl-1-methylimidazolium chloride dissolved in 20 cm ³ of distilled water was added to solution ₃ . The reaction proceeded for 24 hours at 298 K. At the bottom of the flask to obtain ₃ hydrophobic thick, tarry gunk. After the water was separated off, the residue was dissolved in 20 cm ^{3 of} chloroform. The resulting solution was washed with water in a separating funnel until all chlorides were removed. The content of inorganic salt was monitored with an aqueous solution of silver nitrate. After phase separation, chloroform was evaporated from the organic phase. The residue was dried at 353 K under reduced pressure.

The compound structure was confirmed by elemental CHN analysis for C38H41Br2N6O11 (M = 917.57):

values calculated in%: C = 49.74: 11 = 4.50: N = 9.16: values obtained in%: C = 49.52: H = 4.33: N = 8.91.

P r z x l a d II

Eosinate B 3-decyloxymethyl-1-methylimidazolium ₃

To a 100 cm ³ round-bottom flask equipped with a magnetic stirrer, 0.005 mol of eosin B in the form of salt, dissolved in 20 cm of distilled water, was introduced and ₃

0.009 mol of 3-decyloxymethyl-1-methylimidazolium chloride dissolved in 10 cm ³ of distilled water. The reaction mixture was vigorously stirred for 24 hours at the temperature of 298K. ₃ was then separated water from hydrophobic product, which is dissolved in 20 cm ³ of chloroform. The chloroform solution was washed with distilled water until the sodium chloride was completely removed from the chloroform phase. The presence of chlorides was checked with an aqueous solution of silver nitrate. After evaporating the chloroform, the residue was dried at 353K under reduced pressure. The product obtained was a green wax. Dissolved in acetone, it has acquired a very bright orange color. The purity of the obtained compound was determined on the basis of a two-phase titration (PN-HN-ISO-2871-1), obtaining a cationic active substance content of 70.5%.

The structure of the compound was confirmed by performing proton and carbon nuclear magnetic resonance spectra:

¹ H NMR (DMSOcfe) = 0.840 ppm (t, J = 4.4 Hz, 6H): 1.207 (m, 28H): 1.467 (m, 4H) 3.459 (t, J = 4.3 Hz, 4H): 3.901 (s, 6H): 5.571 (s, 4H): 6.517 (s, 1H): 7.057 (d, J = 3.1 Hz, 1H): 7.326 (1, J = 3.3 Hz, 1H): 7.510 (1, J = 2.5 Hz, 1H): 7.783 (d, J = 5.3 Hz, 2H): 7.866 (d, J = 4.1 Hz, 2H): 7.994 (d, J = 1.9 Hz, 1H): 9.473 (s, 2H):

¹³ C NMR (DMSOcfe) ppm = 13.954: 22.112: 25.321: 28.644: 28.708: 28.964: 28.991: 30.680: 31.301: 35.916: 69.159: 78.089: 101.339: 121.868: 124.023: 124.712: 127.342: 127.730: 129.003: 129.145: 129.012: 130,158: 130,423: 134,285: 135,426: 137,380: 152,541: 163,118: 168,350.

PL 212 902 B1

Elemental analysis of CHN for C50H65Br2N6O11 (M = 1857.89): values calculated in%: C = 55.30: H = 6.03: N = 7.74: values obtained in%: C = 55.12: H = 5 , 81: N = 7.56.

P r x l a d III

Eosinate B 3-dodecyloxymethyl-1-methylimidazolium

In a round-bottom flask equipped with a magnetic stirrer, 0.004 mol ₃ of eosin B sodium salt was dissolved in 30 cm ³ of distilled water. A 2-fold molar excess of ₃ -dodecyloxymethyl-1-methylimidazolium chloride dissolved in 20 cm ³ of distilled water was added to the solution.

The reaction was carried out for 24 hours at the temperature of 295K. A hydrophobic, thick, tarry goo was obtained at the bottom of the flask. After separating the water. the residue is dried at. 353K under reduced these _three pressure. The product was then dissolved in 50 cm ^{3 of} anhydrous acetone. The precipitate was filtered off and the filtrate's solvent was evaporated. The residue was dried at 353 K under reduced pressure. The product was obtained in the form of a thick black wax.

The purity of the obtained compound was determined on the basis of a two-phase titration (PN-KN-ISO-2871-1), resulting in a cationic active substance content of 85%.

The compound structure was confirmed by elemental CHN analysis for C54H73Br2N6O11 (M - 1141.99):

values calculated in%: C = 56.76: 11 = 6.44: N = 7.36:

values obtained in%: C - 56.55: H = 6.14: N = 7.15.

P r x l a d IV

3-butoxymetyIo-1-methylimidazolium eosinate ₃

The reactor was charged 0.005 mol of the sodium salt of Eosin Y dissolved in 30 cm ^{3 of} distilled water were added 0.010 mol of 3-butoksymetyIo 1 metyIoimidazoliowego ₃ dissolved in 20 cm ³ of distilled water. With intensive stirring at the temperature of 353K for 24 hours, the product in the form of a green wax appeared. After separation of water, the residue was dried in a temperatu ₃ sculpture 353 K, under reduced pressure. The product was then dissolved in 50 cm ^{3 of} anhydrous acetone. The precipitate was filtered off and the filtrate's solvent was evaporated. The residue was dried at 353 K under reduced pressure. The product was obtained as a green wax.

The structure of the compound was confirmed by performing proton and carbon nuclear magnetic resonance spectra:

¹ H NMR _(DMSOd6) 5ppm = 0.828 (1, J = 4.8 Hz, 6H): 1.242 (m, 411): 1.459 (m, 4H) 3.455 (1, J = 4.2 Hz, 4H) : 3.867 (s, 6H): 5.532 (s, 4H): 6.306 (s, 1H): 6.593 (s, 1H): 6.905 (d, J = 4.0 Hz, 1H): 7.274 (t, J = 2 , 2 Hz, 1H): 7.630 (t, J = 3.0 Hz, 1H): 7.754 (d, 2H): 7.847 (d, 2H): 8.073 (d, J = 4.5 Hz, 1H): 9.426 (s, 2H):

¹³ C NMR _(DMSOd6) 5ppm = 13.598: 18.546: 30.680: 35.898: 68.854: 99.125: 109.446 1 17.997: 121.850: 124.009: 129.095: 129.186: 129.378: 129.451: 129.729: 129.899: 130.345: 132.824: 137.293: 152.911: 167.218: 167.323: 168.167,

Elemental analysis of CHN for C38H41Br4N4O7 (M = 985.37): values calculated in%: C = 46.32: H = 4.19: N = 5.69: values obtained in%: C = 46.14: 11 = 3 , 92: N = 5.35.

P r z k ł a d V

3-decyloxymethyl-1-methylimidazolyl eosinate Y ₃

In a round-bottom flask, equipped with a magnetic stirrer, 0.004 mol of Eosin Y salt was dissolved in 30 cm ³ of distilled water. A two-fold molar excess of chloride ₃ was added to the solution.

3-decyloxymethyl-1-methylimidazolium, dissolved in 20 cm ³ of distilled water. The reaction was carried out for 24 hours at a temperature of 315 K. The reaction product came out in the form of a liquid bottom layer. After the water was separated off, the residue was dried at 353 K under reduced pressure. ₃ was then dissolved in 50 cm ³ of anhydrous acetone. The precipitate was filtered off and the filtrate's solvent was evaporated. The residue was dried at 353K under reduced pressure.

The purity of the obtained compound was determined on the basis of a two-phase titration (PN-KN-ISO-2871-1), resulting in a cationic active substance content of 97.5%.

The structure of the compound was confirmed by performing proton and carbon nuclear magnetic resonance spectra:

¹ H NMR (DMSOcfe) 5ppm = 0.840 (t, J = 4.4 Hz, 6H): 1.198 (m, 28H): 1.447 (m, 4H) 3.429 (t, J = 4.3 Hz, 4H): 3.853 (s, 6H): 5.522 (s, 4H): 6.265 (s, 1H): 6.631 (s, 1H): 7.106 (d, J = 2.7 Hz, 1H):

PL 212 902 B1

7,500 (t, J = 2.5 Hz, 1H): 7.765 (d, 2H): 7.848 (d, 2H): 8.018 (t, J = 2.9 Hz, 1H): 8.364 (d, 1H): 9.571 (s, 2H):

¹³ C NMR (DMSOcfe) 5ppm = 13.965: 22.109: 25.328: 28.658: 28.704: 28.714: 28.956: 28.988: 31.291: 35.802: 69.087: 79.175: 98.799: 109.409: 117.539: 121.646: 123.790: 127.962: 128.195: 128.530: 129.014: 129.511: 129.646: 129.888: 132.186: 137.279: 152.675: 167.210: 167.814.

Elemental CHN analysis for C50H65Br4N4O7 (M = 1 153.69): values calculated in%: C = 52.05: H = 5.68: N = ^: 4.86: values obtained in%: C = 51.83: H = 5.38: N = 4.55.

P r x l a d VI

3-dodecyloxymethyl-1-methylimidazolium-eosinate ₃

0.004 mol of Eosin Y salt dissolved in 30 cm ³ of distilled water was introduced into the reactor. To the solution was added 0.009 mol of 3-dodecyIoksymetyIo 1 metyIoimidazoliowy rozpuszczo nego ₃ in 20 cm ³ of distilled water. The reaction was carried out for 24 hours at the temperature of 298K. After the water was separated off, the residue was dried at 353 K under reduced pressure. The ₃ product was then dissolved in 50 cm ^{3 of} anhydrous acetone. The precipitate was filtered off and the filtrate's solvent was evaporated. The residue was dried at 353K under reduced pressure. The product was obtained in the form of thick tar. The purity of the obtained compound was determined on the basis of a two-phase titration (PN-EN-ISO-2871-1), resulting in a cationic active substance content of 93%.

The structure of the compound was confirmed by performing proton and carbon nuclear magnetic resonance spectra:

¹ H NMR (DMSOcfe) 5ppm = 0.847 (t, J = 4.4 Hz, 6H): 1.219 (m, 36H): 1.458 (m, 4H) 3.442 (t, J = 4.3 Hz, 4H): 3.865 (s, 6H): 5.534 (s, 4H): 6.277 (s, 1H): 6.614 (s, 1H): 7.013 (d, J = 8.4 Hz, 1H): 7.137 (1, J = 1, 3 Hz, 1H): 7.532 (t, J = 1.5 Hz, 1H): 7.769 (d, 2H): 7.853 (d, 2H): 8.031 (d, J = 1.6 Hz, 1H): 9.509 ( s, 2H):

¹³ C NMR (DMSO from ₆ ) 5ppm = 13.954: 22.112: 25.330: 28.658: 28.731: 29.009: 29.032: 29.064: 31.310: 35.857: 69.155: 78.016: 98.979: 109.533: 117.778: 121.841: 123.977: 128.583: 128.780: 128.875: 128.875: 128.975: : 129,049: 129,528: 129,889; 129.980: 130.177: 132.514: 137.385: 152.906: 167.451: 168.085.

Elemental analysis of CHN for C54H73Br4N4O7 (Μ = 1209.79): values calculated in%: C = 53.61: H = 6.08: N = 4.63: values obtained in%: C = 53.40: 11 = 5.85: N = 4.40.

Example VII

3-Butoxymethyl-1-methylimidazolium erythrosinate ₃

A round bottom flask with a capacity of 100 cm ^3, equipped with a magnetic stirrer, Can you ₃ czono salt, erythrosine 0.004 mol dissolved in 30 cm ³ of distilled water. ₃ was added to the solution

0.009 mol of 3-butoxymethyl-1-methylimidazolium chloride dissolved in 20 cm ³ of distilled water. The reaction was carried out for 24 hours at the temperature of 298K. After the water was evaporated, the residue ₃ was dried at 353K under reduced pressure. The product was then dissolved in 50 cm ^{3 of} anhydrous acetone. The precipitate was filtered off and the filtrate's solvent was evaporated. The residue was dried at 353K under reduced pressure.

The structure of the compound was confirmed by performing proton and carbon nuclear magnetic resonance spectra:

¹ H NMR _(DMSOd6) 5ppm = 0.832 (1, J = 4.8 Hz, 6H): 1.245 (m, 4H): 1.460 (m, 4H) 3.477 (1, J = 2.6 Hz, 4H) : 3.861 (s, 611): 5.529 (s, 4H): 6.872 (s, 2H): 7.105 (d, J = 4.1 Hz, 1H): 7.247 (t, J = 3.1 Hz, 1H): 7.535 (t, J = 2.4 Hz, 1H): 7.754 (d, J = 1.6 Hz, 2H): 7.845 (d, J = 1.6 Hz, 2H): 8.024 (d, J = 4, 5 Hz, 1H): 9.456 (s, 2H):

¹³ C NMR (DMSO from ₆ ) 5ppm = 13.644: 18.569: 30.691: 35.919: 68.817: 75.003: 77.994: 95.194: 111.478: 120.316: 121.674: 123.851: 128.144: 128.544: 128.874: 129.790: 130.009; 132.516: 137.131: 137.670: 156.982: 167.019: 171.001.

Elemental CHN analysis for C38H41I4N4O7 (M = 1173.37): values calculated in%: C = 38.90; H = 3.52: N = 4.77: values found in%: C = 38.71; H = 3.30: N = 4.56,

P r x l a d VIII

3-decyloxymethyl-1-methylimidazolium erythrosinate

To a round-bottomed flask equipped with a magnetic stirrer, 0.004 mol of erythrosine salt ₃ dissolved in 30 cm ³ of distilled water was introduced and 0.008 mol of 3-decyloxymethyl-16 chloride was added.

PL 212 902 B1 ₃

-methylimidazolium dissolved in 20 cm ³ of distilled water. The reaction was carried out for 24 _{three hours} at a temperature of 298K. After the water has evaporated. the residue was dissolved in 20 cm ^{3 of} chloroform and washed with distilled water until the sodium chloride was completely removed from the chloroform phase. The content of chloride ions was checked with an aqueous solution of silver nitrate. After removing the solvent from the organic phase, the residue was dried at 353K under reduced pressure. The purity of the obtained compound was determined on the basis of two-phase titration (PN-EN-ISO-2871-1), obtaining the cationic active substance content of 87.5 ° C.

The compound structure was confirmed by elemental CHN analysis for C50H65I4N4O7 (M = 1341.69):

values calculated in%: C = 44.76: H = 4.88: N = 4.18: values obtained in%: C = 44.5 1:11 = 4.65: N = 3.95.

P r x l a d IX

3-dodecyloxymethyl-1-methylimidazolium erythrosinate ₃

0.004 mol of erythrosine sodium dissolved in 30 cm ³ of distilled water was introduced into the reactor. With vigorous stirring the solution was added 0.008 mol of _3-3 dodecyIoksymetyIo

-1-methylimidazolium dissolved in 20 cm ³ of distilled water. The reaction was carried out for hours at 298K. After the water has evaporated. the residue was dried at 353K ₃ under reduced pressure. The product was then dissolved in 50 cm ^{3 of} anhydrous acetone. The precipitate was filtered off and the filtrate's solvent was evaporated. The residue was dried at 353K under reduced pressure. The purity of the obtained compound was determined on the basis of a two-phase titration (PN-EN-ISO-2871-1), resulting in a cationic active substance content of 82%.

The compound structure was confirmed by elemental CHN analysis for C54H73I4N4O7 (M = 1397.79):

values calculated in%: C = 46.40: H = 5.26: N = 4.01: values obtained in%: C = 46.10: 11 = 5.05: N = 3.80.

P r z k ł a d X

3-Butoxymethyl-1-methylimidazolium fluoresceinate

To a round-bottomed flask equipped with a magnetic stirrer, 0.007 moles of the salt _{3 of} fluorescein dissolved in 30 cm ³ of distilled water were introduced. A 2-fold excess of ₃ molar 3-butoxymethyl-1-methylimidazolium chloride dissolved in 20 cm ³ of distilled water was added to the solution. The reaction was carried out for 24 hours at the temperature of 298K. After the water was evaporated, the residue ₃ was dried at 353K under reduced pressure. The product was then dissolved in 50 cm ^{3 of} anhydrous acetone. The precipitate was filtered off and the filtrate's solvent was evaporated. The residue was dried at 353 K under reduced pressure.

The structure of the compound was confirmed by performing proton and carbon nuclear magnetic resonance spectra:

¹³ C NMR (DMSOd 6) 5ppm = 0.830 (t, J = 4.9 Hz, 6H): 1.243 (m, 4H): 1.457 (m, 4H): 3.462 (1, J = 4.3 Hz, 4H): 3.869 (s, 6H): 5.555 (s, 4H): 6.327 (t, J = 1.8 Hz, 1H): 6.601 (s, 1H): 6.631 (d, J = 1.2 Hz, 1H): 7.111 (d, J = 1.4 Hz, 1H): 7.139 (d, J = 1.6 Hz, 1H): 7.571 (1, J = 3.0 Hz, 1H): 7.792 (d, 2H): 7.875 ( d, 2H): 7.975 (d, J = 1.8 Hz, 1H): 9.562 (s, 2H):

¹³ C NMR _(DMSOd6) 5ppm = 13.497: 18.546: 30.681: 35.835: 68.766: 77.919: 102.273: 109.548: 118.641: 120.302: 121.651: 123.809: 127.060: 127.562: 128.144: 128.469: 129.530: 129.846: 130.307: 137.191: 137.679 : 155,135: 168,526.

Elemental analysis of CHN for C38H45N4O7 (M = 669.78): values calculated in%: C = 68.14: H = 6.77: N = 8.36: values obtained in%: C = 67.90: H = 6 , 52: N = 8.15.

P r z x l a d XI

3-decyloxymetyIo-1-methylimidazolium fluoresceinate ₃

A round bottom flask with a capacity of 100 cm ^3, equipped with a magnetic stirrer, Can you czono ₃ 0.006 mol of sodium fluorescein dissolved in 30 cm ³ of distilled water.

To the solution was added 0.012 mol of 3-decyloksymetyIo 1 metyIoimidazoliowy ₃ dissolved in 20 cm ³ of distilled water. The reaction was carried out for 24 hours at the temperature of 298K. After the water has evaporated. the residue was dried at 353K under reduced pressure. The dried product was dissolved in _{3 of} a size of 20 cm ³ of anhydrous acetone, dropped from the inorganic salt as a solid. After the precipitate was filtered off, the filtrate's solvent was evaporated, and the residue was dried at the temperature of 353K

PL 212 902 B1 under reduced pressure. The purity of the obtained compound was determined on the basis of two-phase titration (PN-EN-ISO-2871-1), obtaining the cationic active substance content of 78%.

The structure of the compound was confirmed by performing proton and carbon nuclear magnetic resonance spectra:

¹ H NMR (DMSOd 6) 5ppm = 0.845 (1, J = 4.5 Hz, 6H): 1.205 (m, 28H): 1.446 (m, 4H): 3.428 (t, J = 4.3 Hz, 4H): 3.829 (s, 6H): 5.515 (s, 4H): 6.053 (t, J = 4.3 Hz, 1H): 6.119 (s, 1H): 6.623 (d, J = 4.5 Hz, 1H): 7.031 (d, J = 2.2 Hz, 1H): 7.053 (d, J = 1.0 Hz, 1H): 7.431 (t, J = 2.4 Hz, 1H): 7.771 (d, 2H): 7.849 ( d, 2H): 7.962 (d, J = 3.1 Hz, 1H): 9.61 7 (s, 2H):

¹³ C NMR (DMSO-d6) 5 ppm = 13.974: 22.128: 25.351: 28.681: 28.718: 28.737: 28.974: 29.002: 31.309: 35.770: 69.068: 77.887: 102.269: 109.082: 120.288: 121.641: 123.786: 127.665: 128.158: 128.455: 128.986: 129.958: 134.404: 137.386: 137.684: 141.316: 156.898: 168.642: 178.224.

CHN elemental analysis for C50H69N4O7 (M = 838.10): values calculated in%: C = 71.65: H = 8.30: N = 6.68: values obtained in%: C = 71.47: H = 8 , 13: N = 6.45.

P r x l a d XII

3-dodecyloxymetyIo-1-methylimidazolium fluoresceinate ₃

0.006 mol of fluorescein salt dissolved in 30 cm ³ of distilled water was introduced into the reactor. To the solution was added 0.013 mol of _{3-dodecyloksymetyIo-1-3-methylimidazolium} dissolving baggage as 20 cm ³ of distilled water. The reaction was carried out for 24 hours at the temperature of 298K.

After water was evaporated, the residue was dried at 353K under reduced pressure. ₃ was then dissolved in 50 cm ³ of anhydrous acetone, the precipitate was filtered off, and the filtrate solvent was evaporated. The residue was dried at 353K under reduced pressure.

The purity of the obtained compound was determined on the basis of a two-phase titration (PN-EN-ISO-2871-1), resulting in a cationic active substance content of 98.5%.

The compound structure was confirmed by elemental CHN analysis for C54H77N4O7 (Μ = 894.21):

values calculated in%: C = 72.53: H = 8.68: N = 6.27: values obtained in%: C = 72.30: 11 = 8.45: N = 6.05.

Claims (3)

1. Colored imidazolium salts of the general formula, in which R ¹ is a proton or bromine, or 234 iodine, or nitro group, R ² is proton or bromine, or iodine, R ³ is proton or bromine or iodine, R ⁴ 5 is proton or bromine, or iodine, or nitro group, R ⁵ is straight chain alkyl group containing from 2 to 12 carbon atoms. ₁ Process for the preparation of colored imidazolium salts of general formula I, wherein R ¹ is a proton or bromine, or iodine, or a nitro group, R ² is a proton or bromine, or iodine, R ³ is propton or bromine, or iodine, R ⁴ is a proton or bromine, Iub iodine, Iub nitro, R ⁵ is a straight chain alkyl group containing from 2 to 12 carbon atoms, characterized in that the halides imidazole ₅ zoliowe of general formula 2 wherein R ⁵ is a straight chain alkyl group, containing from ₁ 2 to 12 carbon atoms are reacted with an organic salt of the general formula 3 in which R ¹ is proton or bromine, or iodine, or a nitro group, R ² is a proton or bromine or iodine, R ³ is a proton or bromine , Or iodine, R ⁴ is a proton or bromine or iodine or a nitro group, M is a potassium or sodium or ammonium cation, in a molar ratio of 2: 1 at a temperature of 298K to 353K, preferably 298K in an aqueous medium, and then the solvent is evaporated under reduced ₃ pressure at a temperature of 293 K to 353K, preferably 318 K, adding 50 cm ³ of anhydrous acetone, and the precipitate is separated, evaporated acetone and dried under reduced pressure at a temperature of from 303K to 373K. ₁ Process for the preparation of colored imidazolium salts of the general formula I, wherein R ¹ is a proton or bromine or iodine or a nitro group, R ² is a proton or bromine, or iodine, R ³ is propon or bromine, or iodine, R ⁴ is a proton or bromine, Iub iodine, Iub nitro, R ⁵ straight chain alkyl group containing from 2 to 12 carbon atoms, characterized in that halides, imidazolium ₅ of formula 2 wherein R ⁵ is a straight chain alkyl group having from 2 up to 12 ₁ carbon atoms, is reacted with an organic salt of the general formula 3 in which R ¹ is propton or bromine, or iodine, or a nitro group, R ² is a proton or bromine, or iodine, R ³ is a proton or PL 212 902 B1 bromine or iodine, R ⁴ is a proton or bromine or iodine, or a nitro group, M is potassium or sodium, or ammonium, in a molar ratio of 2: 1 at a temperature of 298K to 353K, preferably 298K, in the environment _{3 with} water, then 20 cm ^{3 of} hydrophobic organic solvent are added, then the organic layer is rinsed with distilled water until the disappearance of halogen ions in the effluent, the solvent is further evaporated under reduced pressure at a temperature above 298 K and dried under reduced pressure at a temperature of above 298K.