Method of cold dyeing with insoluble azo colourants of fibrous materials

FIELD: textile industry.

SUBSTANCE: invention can be used the most effectively in the field of dyeing and finishing works to increase the range of colours when colouring with insoluble azo colourants of fabrics from natural fibers. The cold dyeing method with insoluble azo colourants of fibrous materials of natural fibers is carried out by impregnating with the solution of azo dyestuff component followed by treatment with a diazonium salt. As azo dyestuff component the solution of methyl phloroglucinol is used with a concentration of 5 g/l, soaking with it is carried out for five minutes at a liquor ratio 1:20 at a temperature of 50-60°C, diazonium salt is used at a concentration of 10 g/l and processing with it is carried out for 20-25 minutes at 10-15°C.

EFFECT: invention enables to simplify dyeing of fibrous materials, to recycle unusable explosives.

1 tbl, 3 ex

 

The invention relates to the field of textile industry, and more specifically to a method for production of azo dyes on the fiber using cold dyeing. The invention can most effectively be used in the field of dyeing and finishing production to extend the range of colors when dyeing insoluble azo dyes fabrics of protein and cellulose fibers.

There is a method of cold dyeing wool provides for the impregnation of wool aqueous-alkaline solution of azo-components, which use water-alkaline extract of buckwheat in module baths 1:50 at 20°C for 12-24 h at 70-80°C for 20-30 min followed by treatment of the salt of the page, taken in an amount of 1-2% by weight of wool, at 10-15°C for 10-15 min (patent RF №2110632, publ. 10.05.1998). The disadvantage of this method of dyeing are the duration of the dyeing, the use of an alkaline solution of azo-components and coloring in a narrow range of colors.

There is a method of cold dyeing cellulosic materials using as azo-components at dyeing 4,4'-deoxycytidylate with dissolution in alkali for application to cellulosic material (copyright certificate №133856, publ. bull. No. 23 of 1960). The main disadvantage of dyeing this method is the use of an alkaline solution of azo-components and coloring in a narrow range of colors.

The known method the crash is of wool and silk ice dyes using as azo-components of the connection, obtained by condensation of 2,3-oximately acid with amino compounds of the aromatic series, with subsequent transformation of anilides in the Quaternary salt by heating with alkylating agents (copyright certificate №93496, publ. in bull. No. 4 1952 - prototype). The disadvantage of this method of dyeing with these dyes is the need for a synthesis of azo-components representing derivatives of 2-hydroxy-3-naphthoic acid. Such a synthesis is possible only in conditions of multi-stage, complex and expensive process.

The proposed method is intended to replace the already known methods suffer from some major drawbacks. As you know, for the formation of insoluble azo dyes the fabric is impregnated with an alkaline solution of azo-components, dried at relatively high temperatures of 50-60°C, and the alkali, concentrating, debilitating effect on the fabric. In addition, fabric, prodluzovani alkaline solution of azo-components, may not, without harm to persist for a long time (more than a day), as under the influence of light and air, oxidation occurs, the tissue turns brown and when the diazotization color is not bright, as usual, and dirty-dim.

In the proposed method, the above drawback is eliminated by the fact that as azo-components of the mixture is applied metallo glucina, does not require to store for the azocoupling reaction in an alkaline environment.

The technical result of the present invention is to create a new way of ice dyeing fibrous materials using as azo-components of a new product chemical modification of 2,4,6-trinitrotoluene - methyl phloroglucinol used (Fig), which avoids the synthesis of complex molecules isotalo, to expand the range of dyes and at the same time to dispose of unusable explosives.

Technical result is achieved by the proposed method lies in the fact that the cold dyeing insoluble azo dyes fibrous materials from natural fibers is carried out by impregnation with a solution of azo-components followed by treatment of the salt of the page. As azo-components using a solution of methyl phloroglucinol used with a concentration of 5 g/l, the impregnation of them are 5 minutes at module baths 1:20 at a temperature of 50-60°C. Sol, page used with a concentration of 10 g/l and handling it are 20-25 minutes at 10-15°C.

To achieve a more intense color wool fabric processing, MFG lead again on the same technology. Then the fabric is squeezed, dried, and then treated with salt, page in acidic or neutral medium.

The color of the obtained dyed little depends on the structure of the Oia methyl phloroglucinol used and is determined by the structure of azalina. In this method of dyeing obtained a wide range of colors (About orange, pink and fast scarlet salt b - color yellow and red scales; diazelam purple, fast bordeaux gp salt and fast blue salt gr - color blue-purple spectrum). The proposed method is of great economic importance. Processing salt, page in acidic or neutral medium for fabrics made of natural fibers reduces the damage of protein and fiber. This method allows you to achieve a great variety of colors and shades for natural fibers.

Using a solution of methyl phloroglucinol used for treatment of fibrous materials with ice dyeing in combination with the diazonium compounds enables to receive labels with characteristics of resistance to physico-mechanical stress, which is not inferior to similar measures for fully synthetic dyes. Samples were tested for performance and found that the resistance to washing, dry and wet friction is 4-5 points on a scale of gray samples.

The following examples explain the present invention. In the examples, wool, silk, cotton is used in the form of a fabric.

Example 1. Ice dyeing wool by treating a solution of methyl phloroglucinol used and the salt of the page based on 2,5-dichloraniline. 5 g of wool, pre-soaked in distilled water and wrung out, pour R is the target Fig a concentration of 5 g/l module when the bath 20 in the amount of 100 ml (solid content per 100 ml of the substance 0.5 g). The wool is treated at 60°C for 5 minutes. After processing Fig wool wring out, leave in the open access of air for 15-20 minutes and then treated with the same solution MFG at 60°C for 5 minutes, dried and filled with a solution of diazonium salts to mix directly on the fiber.

Preparation of a solution of diazonium salts Fast Scarlet Saltr. 10 g Fast Scarlet Saltr dissolved in 1000 ml of warm distilled water (solid content per 100 ml of the substance 1 g), cooled on the outside and add conc. HCl to pH ≤3,5. For a combination of 5 g of wool take 100 ml of the solution of diazonium salts (module baths 20). The combination is carried out at a temperature of 10-15°C for 20 minutes the Sample is well washed with warm running water, malout and again washed with water and dried in the open air during the day. Coat color is orange - red.

Example 2. Ice dyeing silk by treating a solution of methyl phloroglucinol used and the salt of the page on the basis of 5-nitro-2-aminoanisole. Solution preparation MFG for sample silk weight 5 g are as in example 1.

Silk is treated at a temperature of 50°C for 5 minutes. After processing, MFG natural silk press, leave in the open access of air for 15-20 minutes, dried and filled with a solution of diazonium salts to mix directly on the fiber.

Need a kitchen the other solution diazole pink O. 10 g of diazole pink dissolved in About 1000 ml of warm distilled water (solid content per 100 ml of the substance 1 g). Then the solution is cooled from the outside and gradually add conc. HCl to pH ≤3,5. For a combination of 5 g of silk take 100 ml of the solution of diazonium salts (module baths 20). The combination is carried out at a temperature of 10-15°C for 20 minutes Washing and drying the samples, as in example 1. Coat color is yellowish-pink.

Example 3. Ice dyeing cotton by treatment with a solution of methyl phloroglucinol used and the salt of the page on the basis of 3-amino-6-benzoylamine 4-methoxytoluene. Solution preparation MFG for sample silk weight 5 g are as in example 1.

The cotton is treated at 60°C for 5 minutes. After processing Fig cotton wring out, leave in the open access of air for 15-20 minutes, dried and filled with a solution of diazonium salts to mix directly on the fiber.

Preparation of the solution of diazole purple. 10 g of diazole filetosave dissolved in 1000 ml of warm distilled water (solid content per 100 ml of the substance 1 g). Then the solution is cooled from the outside and bring the pH of the environment to the interval of 4.5 to 6.5. For a combination of 5 g of cotton take 100 ml of the solution of diazonium salts (module baths 20). The combination is carried out at a temperature of 10-15°C for 20 minutes Washing and drying the samples, as in example 1. Color cotton purple with red ottink the M.

Characteristics of stability stained tissue samples for physico-chemical and physico-mechanical effects are presented in the table.

As can be seen from the table, the stability of the dyed wool samples and physico-chemical effects is satisfactory.

At the same time applying a new azocompound MFG product obtained by treatment of obsolete raw materials, allows with one hand, to solve the environmental problem in the country, and on the other, to expand the color gamut of azo dyes.

The stability of the obtained dyed to physico-chemical and physico-mechanical
SampleColor stability
Resistant to frictionResistance to washing. Change the initial coloring/shading of the white sample/shading of adjacent sample
Resistance to dry friction. Lightening initial coloring/shading white sampleResistance to wet abrasion. Lightening initial coloring/shading white sample
1 234
Wool (Fig and salt the page based on 2,5-dichloraniline)5/45/45/4/5
Silk (Fig and salt the page on the basis of 5-nitro-2-aminoanisole)5/55/55/4/4
Cotton (MFG and salt the page on the basis of 3-amino-6-benzoylamine 4-methoxytoluene)5/55/55/4/4

How cold dyeing insoluble azo dyes fibrous materials from natural fibers by impregnation with a solution of azo-components with subsequent processing salt, page, characterized in that as azo-components using a solution of methyl phloroglucinol used with a concentration of 5 g/l, the impregnation of them are 5 min at module baths 1:20 at a temperature of 50-60°C, salt, page used with a concentration of 10 g/l and handling it are 20-25 min at 10-15°C.



 

Same patents:

FIELD: chemistry.

SUBSTANCE: invention relates to a novel crystalline modification of an azo pigment with Colour Index 151, which is meant for pigmentation of macromolecular natural or synthetic organic materials. The invention discloses 2-[[1-[[(2,3-dihydro-2-oxo-1H-benzimidazol-5-yl)amino]carbonyl]-2-oxopropyl]azo] benzoic acid (yellow pigment with Colour Index 151) (I), characterised by value ΔE* (black/white) in the fundamental tone less than 22.0±0.7. Described also is a method for synthesis of the said compound and use thereof in dyeing macromolecular natural or synthetic organic materials.

EFFECT: pigment has high opaqueness and high colour intensity.

7 cl, 2 dwg, 5 ex

FIELD: chemistry.

SUBSTANCE: disclosed is a method of producing mono- or disazo dyes based on methyl phloroglucinol (MPG), involving azo coupling of MPG and a diazonium salt at temperature (-)5 -(+)10°C, pH from less than 1 to 8 and molar ratio of MPG to the diazonium salt between 1:1 and 1:2.

EFFECT: recycling trinitrotoluene using an environmentally and technologically acceptable method to obtain dyes based on MPG with high output and high selectivity, having high resistance to physical and chemical effects compared to analogues on structure and application, for example, azo dyes based on p-cresol.

3 tbl, 15 ex

Dispersed azo dyes // 2376334

FIELD: chemistry.

SUBSTANCE: described are new dispersed azo dyes, which contain cyanmethyl ester groups of formula (I) , in which D, R1-R7, s, n assume values given in paragraph 1 of the formula of invention.

EFFECT: proposed dyes have high colour intensity, resistance to water, are less sensitive to changes in pH of the environment compared to known dyes of this group.

8 cl, 11 tbl, 235 ex

Dispersed azo dyes // 2376334

FIELD: chemistry.

SUBSTANCE: described are new dispersed azo dyes, which contain cyanmethyl ester groups of formula (I) , in which D, R1-R7, s, n assume values given in paragraph 1 of the formula of invention.

EFFECT: proposed dyes have high colour intensity, resistance to water, are less sensitive to changes in pH of the environment compared to known dyes of this group.

8 cl, 11 tbl, 235 ex

Dispersed azo dyes // 2376334

FIELD: chemistry.

SUBSTANCE: described are new dispersed azo dyes, which contain cyanmethyl ester groups of formula (I) , in which D, R1-R7, s, n assume values given in paragraph 1 of the formula of invention.

EFFECT: proposed dyes have high colour intensity, resistance to water, are less sensitive to changes in pH of the environment compared to known dyes of this group.

8 cl, 11 tbl, 235 ex

Dispersed azo dyes // 2376334

FIELD: chemistry.

SUBSTANCE: described are new dispersed azo dyes, which contain cyanmethyl ester groups of formula (I) , in which D, R1-R7, s, n assume values given in paragraph 1 of the formula of invention.

EFFECT: proposed dyes have high colour intensity, resistance to water, are less sensitive to changes in pH of the environment compared to known dyes of this group.

8 cl, 11 tbl, 235 ex

Azo dyes // 2324714

FIELD: chemistry.

SUBSTANCE: scope of invention covers new azo dyes intended to obtain spin dyed plastics or dope-dyed fibers. Azo dyes are described with formula I in which each of R1 and R2 independently from each other are -NH-(CH2CH2)-OH, -NH-CH2-CHOH-CH2-OH, -NH-(CH2CH2)-S-(CH2CH2)-OH, -NH-(CH2CH2)-NH-(CH2CH2)-OH,-NH-(CH2CH2)-NH2,-NH-CH2-CHOH-CH2-NH2, -NH-CH2-CON(CH2CH2OH)2,-NH-CH2CH2-CON(CH2CH2OH)2, , R3 - -CN or -CONH2, R4 - methyl or trifluoromethyl, R5 -CF3, , R6 - hydrogen or chlorine atom and R7 - hydrogen, chlorine, bromine atom, -NO2.

EFFECT: proposed azo dyes possess elevated dying capacity.

5 cl, 18 tbl, 2 ex

FIELD: organic chemistry, azo dyes.

SUBSTANCE: invention relates to azo dyes designated for coloring or printing on synthetic or semisynthetic fibrous materials. Invention describes azo dyes of the formula (1) given in the invention description comprising residue 2-NHR3-3-cyano-4-methyl-NHR2-methylpyridine as azo-containing component wherein R2 means unsubstituted or substituted aryl radical or unsubstituted or substituted aralkyl radical; R3 means unsubstituted or substituted aryl radical or unsubstituted or substituted aralkyl radical under condition that one of substitutes R2 and R3 represents unsubstituted or substituted aryl radical and another substitute represents unsubstituted or substituted aralkyl radical wherein indicated substituted aralkyl radical is not 2-hydroxy-2-phenylethyl. Also, invention describes mixtures comprising at least two structurally different azo dyes of the formula (1), and tricolor mixture based on red azo dye of the formula (1), sky-blue and yellow dye. Dye mixtures based on azo dye of the formula (1) possess the enhanced staining capacity as compared with individual dyes and increased stability of coloring to light and alkali at high temperatures.

EFFECT: improved and valuable properties of azo dyes.

10 cl, 2 tbl, 2 ex

FIELD: organic chemistry, dyes.

SUBSTANCE: invention relates to dispersed dyes based on N-butylphthalimidyldiazo component and aniline azo component that are designated for staining and printing on semisynthetic and synthetic hydrophobic fibrous materials. Invention describes dyes of the formula (1): wherein R1 means hydrogen atom, methyl or -NHCO-(C1-C4)-alkyl; R2 means (C1-C4)-alkyl wherein is possible but optionally the alkyl chain comprising C2- or more carbon atoms is broken by oxygen atom; R3 has any value of R2 but independently on R2. Also, invention describes a mixture of dyes comprising at least two structurally different dyes of the formula (1). Proposed dyes of the formula (1) and mixtures of indicated dyes provide staining on semisynthetic and synthetic fibrous materials with good strength indices, especially, to laundering and perspiration. Proposed dyes of the formula (1) possess the enhanced staining intensity and thermal stability as compared with the known similar dyes comprising ethyl group near nitrogen atom of phthalimidyl radical.

EFFECT: improved properties of dyes.

7 cl, 1 tbl, 3 ex

FIELD: organic chemistry, dyes.

SUBSTANCE: invention relates to the dispersed dyes comprising N-methylphthalimide-diazo-component and a coupling aniline component. Invention proposes a dye of the formula (1): wherein R means hydrogen or bromine atom; R1 means hydrogen atom, methyl or -NHCO-(C1-C4)-alkyl; R2 means (C1-C4)-alkyl substituted with (C1-C4)-alkoxy-group; R3 has any value among R2 being independently of R2. Invention proposes a mixture of dyes comprising at least one azo dye of the formula (1) and at least one azo dye of the formula (4): wherein R1 means hydrogen atom, methyl or -NHCO-(C1-C4)-alkyl; R2 means (C1-C4)-alkyl wherein is possible but not obligatory that C2-alkyl chain or comprising more carbon atoms is broken with oxygen atom, and R has any value of R being independently of R2. Also, invention proposes a method for coloring or printing on semisynthetic or synthetic hydrophobic fibrous materials wherein dye of the formula (1) or mixture of dyes of formulae (1) and (4) is applied on such materials or added in them. Invention proposes dispersed dyes providing coloring characterizing by high strength degree in laundry and against sweat.

EFFECT: valuable properties of dyes.

7 cl, 2 tbl, 3 ex

FIELD: varnish-and-paint industry.

SUBSTANCE: invention discloses azo dyes based on diazotized 3,5-dinitroaniline or 2-amino-4,6-dinitrotoluene with β-naphthol or Azotol A as azo components. These dyes possess elevated heat resistance as compared to known similar-structure dyes based on mono- or dinitroaniline as diazo components, for example pigment Orange 3 and pigment Red 3, which allows their use for dyeing synthetic fibers in bulk.

EFFECT: expanded application possibilities.

5 cl, 4 tbl, 4 ex

FIELD: varnish-and-paint industry.

SUBSTANCE: invention discloses azo dyes based on diazotized 3,5-dinitroaniline or 2-amino-4,6-dinitrotoluene with β-naphthol or Azotol A as azo components. These dyes possess elevated heat resistance as compared to known similar-structure dyes based on mono- or dinitroaniline as diazo components, for example pigment Orange 3 and pigment Red 3, which allows their use for dyeing synthetic fibers in bulk.

EFFECT: expanded application possibilities.

5 cl, 4 tbl, 4 ex

FIELD: organic chemistry, dyes.

SUBSTANCE: invention relates to the dispersed dyes comprising N-methylphthalimide-diazo-component and a coupling aniline component. Invention proposes a dye of the formula (1): wherein R means hydrogen or bromine atom; R1 means hydrogen atom, methyl or -NHCO-(C1-C4)-alkyl; R2 means (C1-C4)-alkyl substituted with (C1-C4)-alkoxy-group; R3 has any value among R2 being independently of R2. Invention proposes a mixture of dyes comprising at least one azo dye of the formula (1) and at least one azo dye of the formula (4): wherein R1 means hydrogen atom, methyl or -NHCO-(C1-C4)-alkyl; R2 means (C1-C4)-alkyl wherein is possible but not obligatory that C2-alkyl chain or comprising more carbon atoms is broken with oxygen atom, and R has any value of R being independently of R2. Also, invention proposes a method for coloring or printing on semisynthetic or synthetic hydrophobic fibrous materials wherein dye of the formula (1) or mixture of dyes of formulae (1) and (4) is applied on such materials or added in them. Invention proposes dispersed dyes providing coloring characterizing by high strength degree in laundry and against sweat.

EFFECT: valuable properties of dyes.

7 cl, 2 tbl, 3 ex

FIELD: organic chemistry, dyes.

SUBSTANCE: invention relates to the dispersed dyes comprising N-methylphthalimide-diazo-component and a coupling aniline component. Invention proposes a dye of the formula (1): wherein R means hydrogen or bromine atom; R1 means hydrogen atom, methyl or -NHCO-(C1-C4)-alkyl; R2 means (C1-C4)-alkyl substituted with (C1-C4)-alkoxy-group; R3 has any value among R2 being independently of R2. Invention proposes a mixture of dyes comprising at least one azo dye of the formula (1) and at least one azo dye of the formula (4): wherein R1 means hydrogen atom, methyl or -NHCO-(C1-C4)-alkyl; R2 means (C1-C4)-alkyl wherein is possible but not obligatory that C2-alkyl chain or comprising more carbon atoms is broken with oxygen atom, and R has any value of R being independently of R2. Also, invention proposes a method for coloring or printing on semisynthetic or synthetic hydrophobic fibrous materials wherein dye of the formula (1) or mixture of dyes of formulae (1) and (4) is applied on such materials or added in them. Invention proposes dispersed dyes providing coloring characterizing by high strength degree in laundry and against sweat.

EFFECT: valuable properties of dyes.

7 cl, 2 tbl, 3 ex

FIELD: organic chemistry, dyes.

SUBSTANCE: invention relates to dispersed dyes based on N-butylphthalimidyldiazo component and aniline azo component that are designated for staining and printing on semisynthetic and synthetic hydrophobic fibrous materials. Invention describes dyes of the formula (1): wherein R1 means hydrogen atom, methyl or -NHCO-(C1-C4)-alkyl; R2 means (C1-C4)-alkyl wherein is possible but optionally the alkyl chain comprising C2- or more carbon atoms is broken by oxygen atom; R3 has any value of R2 but independently on R2. Also, invention describes a mixture of dyes comprising at least two structurally different dyes of the formula (1). Proposed dyes of the formula (1) and mixtures of indicated dyes provide staining on semisynthetic and synthetic fibrous materials with good strength indices, especially, to laundering and perspiration. Proposed dyes of the formula (1) possess the enhanced staining intensity and thermal stability as compared with the known similar dyes comprising ethyl group near nitrogen atom of phthalimidyl radical.

EFFECT: improved properties of dyes.

7 cl, 1 tbl, 3 ex

FIELD: organic chemistry, azo dyes.

SUBSTANCE: invention relates to azo dyes designated for coloring or printing on synthetic or semisynthetic fibrous materials. Invention describes azo dyes of the formula (1) given in the invention description comprising residue 2-NHR3-3-cyano-4-methyl-NHR2-methylpyridine as azo-containing component wherein R2 means unsubstituted or substituted aryl radical or unsubstituted or substituted aralkyl radical; R3 means unsubstituted or substituted aryl radical or unsubstituted or substituted aralkyl radical under condition that one of substitutes R2 and R3 represents unsubstituted or substituted aryl radical and another substitute represents unsubstituted or substituted aralkyl radical wherein indicated substituted aralkyl radical is not 2-hydroxy-2-phenylethyl. Also, invention describes mixtures comprising at least two structurally different azo dyes of the formula (1), and tricolor mixture based on red azo dye of the formula (1), sky-blue and yellow dye. Dye mixtures based on azo dye of the formula (1) possess the enhanced staining capacity as compared with individual dyes and increased stability of coloring to light and alkali at high temperatures.

EFFECT: improved and valuable properties of azo dyes.

10 cl, 2 tbl, 2 ex

Azo dyes // 2324714

FIELD: chemistry.

SUBSTANCE: scope of invention covers new azo dyes intended to obtain spin dyed plastics or dope-dyed fibers. Azo dyes are described with formula I in which each of R1 and R2 independently from each other are -NH-(CH2CH2)-OH, -NH-CH2-CHOH-CH2-OH, -NH-(CH2CH2)-S-(CH2CH2)-OH, -NH-(CH2CH2)-NH-(CH2CH2)-OH,-NH-(CH2CH2)-NH2,-NH-CH2-CHOH-CH2-NH2, -NH-CH2-CON(CH2CH2OH)2,-NH-CH2CH2-CON(CH2CH2OH)2, , R3 - -CN or -CONH2, R4 - methyl or trifluoromethyl, R5 -CF3, , R6 - hydrogen or chlorine atom and R7 - hydrogen, chlorine, bromine atom, -NO2.

EFFECT: proposed azo dyes possess elevated dying capacity.

5 cl, 18 tbl, 2 ex

Dispersed azo dyes // 2376334

FIELD: chemistry.

SUBSTANCE: described are new dispersed azo dyes, which contain cyanmethyl ester groups of formula (I) , in which D, R1-R7, s, n assume values given in paragraph 1 of the formula of invention.

EFFECT: proposed dyes have high colour intensity, resistance to water, are less sensitive to changes in pH of the environment compared to known dyes of this group.

8 cl, 11 tbl, 235 ex

Dispersed azo dyes // 2376334

FIELD: chemistry.

SUBSTANCE: described are new dispersed azo dyes, which contain cyanmethyl ester groups of formula (I) , in which D, R1-R7, s, n assume values given in paragraph 1 of the formula of invention.

EFFECT: proposed dyes have high colour intensity, resistance to water, are less sensitive to changes in pH of the environment compared to known dyes of this group.

8 cl, 11 tbl, 235 ex

Dispersed azo dyes // 2376334

FIELD: chemistry.

SUBSTANCE: described are new dispersed azo dyes, which contain cyanmethyl ester groups of formula (I) , in which D, R1-R7, s, n assume values given in paragraph 1 of the formula of invention.

EFFECT: proposed dyes have high colour intensity, resistance to water, are less sensitive to changes in pH of the environment compared to known dyes of this group.

8 cl, 11 tbl, 235 ex

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