SU1321731A1 - N1n-dimethyldiimide perilene-3,4,9,10 of tetracarboxylic acid with improved coloristic and strength properties on polymeric materials and method of producing same - Google Patents

Abstract

The invention relates to the field of the aniline dye industry, in particular to the pigment N-N-dimethyl-imide perylene-3,4,9,10-tetracarboxylic acid in a new physical form, with maxima of the intensity of reflections on the diffractogram at Bragg angles, 4 & deg. 25.2% 23.7, 13, D, 11.9, 8.1. The pigment is characterized by improved color and strength properties on polymeric materials. In the process of obtaining this pigment, the oxidation of the leuco-compound is carried out in the presence of 1-15% by weight of is -. the naphthalide surfactant surfactant, and methylation is di-. The diimide perylene-3,4,9,10-tetracarboxylic acid diimide salt is directly after oxidation at 65-75 ° C. 2 sec. f-ly. S С /) с с tsD СО

Description

The invention relates to the aniline-dye industry, in particular, to methods for producing a perylene pigment based on an S, N-dimethyldiimide perylene-3,4,9,10-tetracarb onoic acid, used in the paint and varnish industry, printing, for dyeing polymeric materials and syn - Gets in bulk in burgundy color.

The purpose of the invention is to obtain N, N-dimethyldiimide perylene-3,4,9,10-tetracarboxylic acid in a new physical form with improved color and strength properties on polymeric materials using a simplified technology.

S, N-Dimethyldiimide perylene 3,4,9,

t5 5 ma.ch. ceresin, 20 math. paraffin, melt the mass by heating to 80-90 0, add 150 mas. wollastanite, 5 ma.ch. .aerosila, 240 ma.ch. natural chalk, 18 ma.ch.

10-tetracarboxylic acid in the new physical form is characterized by max-20 lanolin, 40 wt.h. glycerol, with intensity simuyami reflexes 7 ma.h. castor oil, 5 mah.

odorants (coniferous extract) and 10 ma.h, pigment. The mass is stirred at 85-95 ° C for 10-15 minutes, "cooled 25 to 20-25 ° C and molded clay, colored red (), characterized by a yellowish tint (, 0) and a pure color tone (, 1) .

PRI me R 5. Dyeing polyester. 1 ma.ch. lavsan crumbs, powdered D, 05 ma.ch. pigment melted down for 1 hour at 280 ° C

on the diffractogram at the Bragg angles, 4; 25.2; 23.7; 13.1; 11.9; 8.1 differs from the pigment in a known physical form with a higher degree of crystallinity (at the corresponding Bragg angles up to 10%) and improved quality, enhanced heat resistance (from 280 to 325 C), weather resistance (from 6 to 7 balances), resistance to (3–4 to 4–5 points), resistant to organic solvents (acetone, benzene, 5% aqueous solution of caustic soda) (from 3-4 to 4–5 points), and also has the advantage of dye concentration (hp), shade (hp) and purity (l S).

Example 1. Dyeing nylon in mass. 1 ma.ch. nylon crosh35

40

, hold for 1 h at au U and from the melt they form a dyed lavsan filament of burgundy color with a yellowish tint (, 8), increased color intensity () and an improved tone purity (, 3).

PRI-m e r 6. Dyeing of polyvinyl chloride. Prepare a mixture of 1 wt. suspension polyvinyl chloride, 0, .h. dibutyl phthalate, 0.05 May, h cadmium stearate, 0.02 wt. titanium dioxide, 0.01 wt. calcium stearate and 0.01 mac. pigment burgundy perylene. The mixture was placed in a thermostat to swell and held for 1 hour at 85 ° C, after which the paste was applied to the glass. Glass with a strip of painted polyvinyl chloride can withstand 10 min. After cooling, the film is removed from the glass. The film has a burgundy color with a yellowish tint (, 0), an increased purity of tone (, 1) and is distinguished by a high intensity of coloring (С 116%).

ki, powdered 0.005-0.01 mach. pigment, melt, hold for 2 hours at 270-275 ° C, and a colored nylon thread is formed from the melt. The color of the yarn obtained is distinguished by high intensity (), yellow tint (, 1) and high purity of tone (, 4).

P. I m e r 2. Dyeing in lacquer. Stir the mixture 1 wt.h. pigment, 25 ma.ch. titanium dioxide, and 17.3 mch. (alkyd or alkydmelamine resin) for 30 minutes and the resulting paste is applied to the coating. The pigment in the enamel coating has a high color intensity (), improved hue (, 2) and color tone purity (, 6).

PRI me R 3. Use in printing. Mix 1 mac. pigment with 4 ma.ch. Drying oils are carefully ground on a three-roll paint mill for three passes. The resulting paste is used for high-quality offset printing. Printed prints have a higher color intensity (), improved hue (, 5) and color tone purity (, 9).

Example4. Dyeing plasticine. In the dispersion mixer load 500 mas. petrolatum,

5 ma.ch. ceresin, 20 math. paraffin, melt the mass by heating to 80-90 0, add 150 mas. wollastanite, 5 ma.ch. .aerosila, 240 ma.ch. natural chalk, 18 ma.ch.

lanolin, 40 ma.ch. glycerol, 7 ma.ch. castor oil, 5 mah.

PRI me R 5. Dyeing polyester. 1 ma.ch. lavsan crumbs, powdered D, 05 ma.ch. pigment melted down for 1 hour at 280 ° C

, hold for 1 h at au U and from the melt they form a dyed lavsan filament of burgundy color with a yellowish tint (, 8), increased color intensity () and an improved tone purity (, 3).

PRI-m e r 6. Dyeing of polyvinyl chloride. Prepare a mixture of 1 wt. suspension polyvinyl chloride, 0, .h. dibutyl phthalate, 0.05 May, h cadmium stearate, 0.02 wt. titanium dioxide, 0.01 wt. calcium stearate and 0.01 mac. pigment burgundy perylene. The mixture was placed in a thermostat to swell and held for 1 hour at 85 ° C, after which the paste was applied to the glass. Glass with a strip of painted polyvinyl chloride can withstand 10 min. After cooling, the film is removed from the glass. The film has a burgundy color with a yellowish tint (, 0), an increased purity of tone (, 1) and is distinguished by a high intensity of coloring (С 116%).

PRI me R 7. Dyeing plastisol 0.1 m.h. pigment mixed

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from 7.9 mach., talc, 4 mach. with a solution of caustic soda, squeeze out 36 g of melted paraffin, 18 may. diimide; salts of diimide perylene 3,4, octyl phthalate and 70 wt.h. polyvinyl chloride emulsion caustic. The Maeeu is thoroughly mixed and a placetiol capable of heat treatment (when) is obtained. The platform has an intense red color with a yellowish tinge (, 4), an increased intensity of 10 mixes 1 coloring intensity (, 4) and an improved purity of tone (, 3 ).

Example 160 g of potassium hydroxide is heated to 150 ° C, 1.7 g of industrial oil and 26 g of J5 triethanolamine are added. 33.5 g of naphthalimide are slowly added to the obtained melt, stirred for 2 hours at 180 ° C, 700 g of water are diluted in masses, cooled until the mixture is added, 0.35 g of canned sodium hydroxide and 120 g of acid are added. - foil soap, oxidized by air, and dipped. The output of the pigment 31.3 g (89%). The filter is filtered, washed with pigment fractogram, as in the example of 5% aqueous solution of potassium hydroxide, pg g

squeeze out. 35.9 g of the di-potassium salt of di- EXAMPLE 12. The imide perylene-3,4,9,10-tetracarbon-25 procedure of Example 8 is carried out using a pependiuyru on an acid in the form of a paste;

. Put 29 g of potassium carbonate sodium hypochlorite in solution in place of air in 500 g of water, add 2 g of alkyl and 1.7 g of the preparation OC-20, instead of can- (C, -C, J-trimethylammonium chloride, and soap Pigment yield: 91%. 66.7 g of benzoyl sulfate methyl ester 30 A diffractogram of the pigment, as in 9 U-tetracarboxylic acid, is suspended in a solution of 29 g of potassium carbonate in 500 g of water, 2 g of alkyl is added (C., -C) -trimethylammonium chloride and 66.7 g of methyl benzene sulphonic ester, heated to, stirred for 3 hours, heated to

h, filter the osa-. dock, wash it with water, isopropyl alcohol and eno with water. Obtain 31.9 g of product in pigment form, 90%. The diffraction pattern of the pigment, as in example 8.

Example 11. The process is carried out according to the method of Example 10 with the difference that instead of caustic potash, an alkaline agent is used as a mixture

acid. Heat to 65 ° C, stir for 3 hours, filter the precipitate and wash it with water. 31.2 g of product are obtained in pigment form. Output 88% (in terms of naphthalimide). The maximum intensity of the reflections on the diffraction pattern at the Bragg angles, 4; 25.2; 23.7; 13.1; 11.9; eight,. .

EXAMPLE 9 160 g of potassium hydroxide are melted by heating with 26 g of a mixture of MDHO-, di- and triethanolamines (1: 1: 1 mass ratio) and 5 g of water with 33.5 g of naphthalimide being slowly added. , stir 3 h at 170-175 ° C and then carry on the process According to the method of example 8. The pigment yield is 31.5 (89%). The diffraction pattern of the pigment, as in example 8.

least 8.

Example 13. The process is carried out according to the method of example 8 with the difference that instead of rosin soap it is used 1.1 g of syntamide-IOj and methylation is carried out at 50 ° C for 5 hours. The pigment yield is 87%. Pigment diffraction pattern as in Example 8. EXAMPLE 14. The process is carried out.

40 according to the method of Example 8, using, at the oxidation stage, 1.7 g of lignopol VFC instead of rosin powder. Pigment yield 88%. The diffraction pattern of the pigment, as in example 8.

45

Example 15. The process is carried out as described in Example 8, using 1.5 g of alkyl- (-C) -benzyldimethylammonium chloride Q at the stage of oxidation. Pigment yield 89%. Diffractogram — Example 10. A mixture of pigment is melted as in Example 8. 160 g of flaked potassium hydroxide and Example 16. The process is carried out with 26 g of triethanolamine by heating to 33.5 g of naphthalimide using the procedure of example 8, using 160 ° C, the oxidation stage 0.2 g of the product is stirred up for 3 hours at 170 seconds, diluted with the model of the salt of 2-naphthalene sulfoxide 700 g of water, cooled to, add 5 g of rosin powder, oxidize with air, filter the precipitate, wash it with 5% aqueous

logo sodium with formaldehyde. The pigment yield is 86%, the diffraction pattern is the same. Example 17. The process is carried out as described in Example 8, using

caustic soda solution, squeeze out 36 dikalevoy; diimide salts of perylene 3,4, stirred 1

ZO g caustic soda and 120 g caustic potassium. The output of the pigment 31.3 g (89%). Pigment diffractogram, as in the example pg g

9, U-tetracarboxylic acid, suspended in a solution of 29 g of potassium carbonate in 500 g of water, 2 g of alkyl- (C. -.-C) -trimethylammonium chloride and 66.7 g of methyl benzene sulphonic acid are added, heated to stir for 3 hours, heat to

h, filter the precipitate, wash it with water, isopropyl alcohol and eno water. Obtain 31.9 g of product in pigment form, 90%. The diffraction pattern of the pigment, as in example 8.

Example 11. The process is carried out according to the method of Example 10 with the difference that instead of caustic potash, an alkaline agent is used as a mixture

least 8.

Example 13. The process is carried out according to the method of example 8 with the difference that instead of rosin Soap 1.1 .g of sintamide-IOj is used and methylation is carried out at 50 ° C for 5 hours. The pigment yield is 87%. Pigment diffraction pattern as in Example 8. EXAMPLE 14. The process is carried out.

40 according to the method of Example 8, using, at the oxidation stage, 1.7 g of lignopol VFC instead of rosin powder. Pigment yield 88%. The diffraction pattern of the pigment, as in example 8.

45

Example 15. The process is carried out as described in Example 8, using 1.5 g of alkyl- (-C) -benzyldimethylammonium chloride Q at the stage of oxidation. Pigment yield 89%. Pigment diffraction pattern as in Example 8. Example 16. The process is carried out according to the method of example 8, using 0.2 g of the product of mutual modem of the salt of 2-naphthalene sulfonic acid in the oxidation stage. Example 15. The process is carried out as described in example 8, using at the oxidation stage 1.5 g of alkyl- (-C) - benzyldimethylammonium chloride. Pigment yield 89%. Diffractogram of pigment as in example 8. Example 16. The process is carried out according to the procedure of Example 8, using, at the stage of oxidation, 0.2 g of the product together sodium salt of sodium 2-naphthalene sulfate with formaldehyde. The pigment yield is 86%, the diffraction pattern is the same. Example 17. The process is carried out as described in Example 8, using

five

oxidation stage 1.5 g polyethylene glycol -115. Vykod pigment 91%, diffraction pattern is the same.

Example 18 The process is carried out as described in Example 8, using, at the stage of oxidation, 1.8 g of superior W-OFP 100. The pigment yield is 90%, the diffraction pattern is the same.

Example 19. The process is carried out according to the method indicated in Example 8, using 1.6 g of sintanol DS-10 at the oxidation stage. Pigment yield 92%. The diffraction pattern of the pigment, as in example 8.

Example 20: The process is carried out as described in Example 8, using 1.7 g of dispersant CC in the oxidation step. Pigment yield 89%. The diffraction pattern of the pigment, as in example 8.

EXAMPLE 21 The process is carried out up to the procedure described in Example 8, using 1.5 g of wetting agent DB at the oxidation stage. Pigment yield 93%. Pigment diffractogram as in Example 8.

Example 22. The process is carried out as described in Example 8, using 1.5 g alkyl-CC in the oxidation step. - S.) -trimethylammonium chloride instead of rosin soap, and at the stage of methylation - 2 g of lauryl pyridinium sulfate as a catalyst and 58 g of dimethyl sulfate as methyl; 13

and- to-

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and strength properties of materials

Claims (2)

1. N, N-Dimethyldiimide perylene-3, A, 9,10-tetracarboxylic acid of the general formula: NSSG , with the maxima of the intensities of the reflections on the diffractogram at the Bragg angles, 4; 25.2 °; 23.7 °; 13, 11.9; 8.1 ° with improved color and strength properties on polymeric materials. 2. The method of producing N, N-dimethyl-diimide perylene-3,4,9,10-retracarboxylic acid by the interaction naphthalimide with caustic potash in tri-ethanolamine, oxidation of the leucodine diimide perylene-3,4,9,10-tetracarboxylic acid, and methylation of the di-meride diimide perylene-3,4, 9,10-tetracarboxylic acid at elevated temperature in the presence of a quaternary ammonium salt, characterized in that in order to improve the colouristic and lasting agent. Pigment yield 86%. His is the cognitive properties of the target product. The diffractogram, as in example 8, The proposed method for producing Bordeaux Perilone pigment simplifies the process and allows to obtain a pigment in a new physical form with improved color schemes. as well as simplifying the technology, the oxidation is carried out in the presence of 1-15% by weight of the surfactant naphthalimide, and methylation is directly after oxidation at 50-90 C. Compiled by A.Molin Editor N.Egorova Tehred A. Kravchuk Proofreader I.Erdeyi Order 2722/18 Circulation 633 Subscription VNIIPI USSR State Committee for inventions and discoveries 113035, Moscow, Zh-35, Raushsk nab., d, 4/5 Production and printing company, Uzhgorod, ul, Proektna, 4 as well as simplifying the technology, the oxidation is carried out in the presence of 1-15% by weight of the surfactant naphthalimide, and methylation immediately after oxidation at 50-90 ° C.