Method for producing aqueous polymer dispersions containing colorants
A polymer and dispersion technology, applied in organic dyes, paper coatings, powder coatings, etc., can solve the problems of unstable sedimentation of polymer dispersions, decreased migration of fluorescent dyes, and limitations of preparation processes.
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Embodiment 1
[0315] Embodiment 1: the preparation of N-nonylperylene-3,4-dicarboximide (dye 10)
[0316] Under nitrogen, 5 g (15.5 mmol) of perylene-3,4-dicarboxylic anhydride (prepared according to Liebigs Ann.1995, 1229-1244), 2.44 g (17 mmol) of n-nonylamine and 75 A mixture of N-methylpyrrolidone (NMP) in mL was heated to 175°C for 1.5 hours. After cooling to room temperature, the resulting precipitate was filtered, washed with methanol and dried at 80° C. under reduced pressure. This gives 5.5 g (79%) of the desired product in the form of dark red crystals with a melting point of 201°C.
[0317] Analytical data for dye 10:
[0318] Elemental analysis (% weight calculated value / measured value):
[0319] C: 83.2 / 83.3; H: 6.5 / 6.5; N: 3.1 / 3.1;
[0320] Mass Spectrum (FD, 8kV): m / z=447 (M + , 100%);
[0321] UV / VIS (CH 2 Cl 2 ): λ max (ε)=482(28791), 500(32531)nm;
[0322] 1 H-NMR (400MHz, CDCl 3): δ=8.02(d, 2H), 7.82(d, 2H), 7.70(d, 2H), 7.59(d, 2H), 7.51(d, 2H), 4.05(m, 2H), ...
Embodiment 2
[0323] Example 2: N-(2,6-diisopropylphenyl)-1,6,9-tris(p-tert-butylphenoxy)-perylene-3,4-diformyl Preparation of amine (dye 11)
[0324] Under stirring, 32.3 grams (45 mmoles) of N-(2,6-diisopropylphenyl)-1,6,9-tribromoperylene-3,4-dicarboximide ( Prepared according to WO96 / 22332 Example 1a), a mixture of 27.0 g (180 mmol) p-tert-butylphenol, 16.6 g (120 mmol) anhydrous finely ground potassium carbonate and 1200 ml N-methylpyrrolidone (NMP) Heat to 120°C for 6 hours. After cooling to room temperature, the reaction mixture was added under stirring in 4500 g of 6% by weight aqueous hydrochloric acid solution, and the mixture was stirred for 2 hours, then the precipitated solid was filtered, washed with water until neutral and placed under reduced pressure in Drying was carried out at 100°C. Filtration through a short column of silica gel using dichloromethane as eluent, followed by removal of the solvent under reduced pressure gave 38.9 g (93%) of the desired product in the f...
Embodiment 3
[0331] Example 3: Preparation of 3-hexyl-9(10)-(6-methacryloyloxy-1-hexynyl)perylene (dye 12a)
[0332] 1 g (2.3 mmol) of 3-hexyl-9(10)-(6-hydroxy-1-hexynyl) perylene (according to Liebigs Ann. / Recueil 1997 , 395-407, prepared by basic hydrolysis of 3-(6-acetoxy-1-hexynyl)-9(10)-hexylperylene) dissolved in 60 ml of anhydrous dioxane, in Heat to 45 °C under nitrogen, mix with 0.75 ml triethylamine and 0.52 ml methacryloyl chloride, stir at 45 °C for 4 hours, then mix with 0.52 ml methacryloyl chloride, stir at 45 °C for an additional 12 hours , cooled to room temperature, mixed with 250 ml of water, and extracted with a total of 350 ml of dichloromethane. The solvent was distilled off under reduced pressure and the residue was chromatographed on silica gel using dichloromethane as eluent. After removal of the solvent under reduced pressure, 790 mg (68%) of the desired product were isolated as a yellow, finely crystalline solid.
[0333] Analytical data for dye 12a:
[0334]...
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