CN112409820B - Reactive dye yellow brown and preparation method and application thereof - Google Patents
Reactive dye yellow brown and preparation method and application thereof Download PDFInfo
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- 239000000985 reactive dye Substances 0.000 title claims abstract description 60
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 238000000034 method Methods 0.000 claims abstract description 21
- 229920000742 Cotton Polymers 0.000 claims abstract description 20
- 150000001875 compounds Chemical class 0.000 claims description 76
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 68
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 60
- 235000010288 sodium nitrite Nutrition 0.000 claims description 30
- -1 alkali metal cation Chemical class 0.000 claims description 26
- 238000006243 chemical reaction Methods 0.000 claims description 26
- 238000003756 stirring Methods 0.000 claims description 23
- 239000002585 base Substances 0.000 claims description 22
- 229910052783 alkali metal Inorganic materials 0.000 claims description 20
- 239000012295 chemical reaction liquid Substances 0.000 claims description 20
- 239000011734 sodium Substances 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- 238000002156 mixing Methods 0.000 claims description 16
- 238000006482 condensation reaction Methods 0.000 claims description 14
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims description 11
- 229910006069 SO3H Inorganic materials 0.000 claims description 10
- 229910006145 SO3Li Inorganic materials 0.000 claims description 10
- 238000005859 coupling reaction Methods 0.000 claims description 10
- HQRPHMAXFVUBJX-UHFFFAOYSA-M lithium;hydrogen carbonate Chemical compound [Li+].OC([O-])=O HQRPHMAXFVUBJX-UHFFFAOYSA-M 0.000 claims description 10
- 229910000028 potassium bicarbonate Inorganic materials 0.000 claims description 10
- 235000015497 potassium bicarbonate Nutrition 0.000 claims description 10
- 239000011736 potassium bicarbonate Substances 0.000 claims description 10
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims description 10
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims description 6
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 claims description 6
- 230000009471 action Effects 0.000 claims description 6
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 6
- 239000004744 fabric Substances 0.000 claims description 6
- 239000005457 ice water Substances 0.000 claims description 6
- 229910004727 OSO3H Inorganic materials 0.000 claims description 4
- 229920000297 Rayon Polymers 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 229910052744 lithium Inorganic materials 0.000 claims description 4
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052700 potassium Inorganic materials 0.000 claims description 4
- 239000002964 rayon Substances 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 229910006127 SO3X Inorganic materials 0.000 claims description 2
- 238000004043 dyeing Methods 0.000 abstract description 52
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 abstract description 20
- 239000000986 disperse dye Substances 0.000 abstract description 10
- 230000008569 process Effects 0.000 abstract description 9
- 238000005265 energy consumption Methods 0.000 abstract description 3
- 230000009257 reactivity Effects 0.000 abstract description 2
- 239000011259 mixed solution Substances 0.000 description 91
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 38
- 239000000243 solution Substances 0.000 description 34
- 239000000203 mixture Substances 0.000 description 21
- 235000017557 sodium bicarbonate Nutrition 0.000 description 19
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 19
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
- 239000000975 dye Substances 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 8
- 229910000029 sodium carbonate Inorganic materials 0.000 description 8
- 235000017550 sodium carbonate Nutrition 0.000 description 8
- 238000004040 coloring Methods 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- 239000007788 liquid Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000011056 performance test Methods 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 238000004321 preservation Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 235000006040 Prunus persica var persica Nutrition 0.000 description 1
- 240000006413 Prunus persica var. persica Species 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000004134 energy conservation Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000012192 staining solution Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
- C09B62/503—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring the reactive group being an esterified or non-esterified hydroxyalkyl sulfonyl or mercaptoalkyl sulfonyl group, a quaternised or non-quaternised aminoalkyl sulfonyl group, a heterylmercapto alkyl sulfonyl group, a vinyl sulfonyl or a substituted vinyl sulfonyl group, or a thiophene-dioxide group
- C09B62/507—Azo dyes
- C09B62/513—Disazo or polyazo dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/04—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring
- C09B62/08—Azo dyes
- C09B62/09—Disazo or polyazo dyes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/38—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using reactive dyes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/58—Material containing hydroxyl groups
- D06P3/60—Natural or regenerated cellulose
- D06P3/66—Natural or regenerated cellulose using reactive dyes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/82—Textiles which contain different kinds of fibres
- D06P3/8204—Textiles which contain different kinds of fibres fibres of different chemical nature
- D06P3/8223—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and ester groups
- D06P3/8238—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and ester groups using different kinds of dye
- D06P3/8252—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and ester groups using different kinds of dye using dispersed and reactive dyes
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Dispersion Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a reactive dye yellow brown and a preparation method and application thereof, wherein the structure of the reactive dye yellow brown is shown as a general formula (I):
Description
Technical Field
The invention belongs to the technical field of dyes, and particularly relates to a reactive dye yellow brown and a preparation method and application thereof.
Background
When the polyester-cotton blended fabric on the market is dyed, a common dyeing method is a two-bath method, namely, the fabric is dyed and washed by disperse dye, and then dyed and washed by reactive dye. Although the homochromatism is good and the fastness is high, the working procedure is long, the energy consumption is excessive, the energy conservation and emission reduction and the clean production of printing and dyeing enterprises are not facilitated, and the problems of color spots and cylinder difference can be generated in the production along with the prolonging of the processing time, so that the product quality and the efficiency are influenced.
In order to solve the problems, many factories search for one-bath one-step dyeing of polyester cotton, but the yellow brown reactive dye still has poor high-temperature resistance, can only dye at about 50 ℃ and is not suitable for one-bath one-step dyeing by matching with disperse dye.
For example, the yellow-brown reactive dye disclosed in Chinese patent CN104830097A and the preparation method thereof, the yellow-brown reactive dye is selected from any one compound in the following general formula, or a mixture prepared by compounding any two or more compounds in the following general formula according to any proportion,
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provide an improved reactive dye yellow brown and a preparation method thereof.
In order to achieve the purpose, the technical scheme adopted by the invention is as follows:
the reactive dye yellow brown has a compound structure shown as a general formula (I):
in the formula:
R1、R2、R3、R4each independently selected from H or an alkali metal cation;
j is selected from
P is selected from an integer between 0 and 3;
F1、F2each independently selected from Y1、SO3Y1、
Or
Said Y is1Is H or alkali metal cation, m and n are respectively and independently selected from integers between 1 and 5;
M1、M2、M3、M4、M5、M6each independently selected from Y2、SO3Y2An alkyl group having 1 to 5 carbon atoms or an alkoxy group having 1 to 5 carbon atoms, Y2Is H or an alkali metal cation;
A1、A2、A3、A4each independently selected from H or an alkali metal cation.
According to some embodiments of the invention, the alkali metal cation is Na, K or Li.
According to some embodiments of the invention, F1、F2Each independently selected from H, SO3H、SO3Na、SO3K、SO3Li、SO2C2H5、SO2C2H4Na、SO2C2H4K、SO2C2H4Li、SO2C2H4OSO3H、SO2C2H4OSO3Na、SO2C2H4OSO3K or SO2C2H4OSO3Li。
According to some embodiments of the invention, the M is1、M2、M3、M4、M5、M6Each independently selected from H, SO3H、SO3Na、SO3K、SO3Li、CH3O or CH3. Preferably, said M1、M6Each independently selected from H, SO3H、SO3Na、SO3K or SO3Li。
According to some embodiments of the invention, p is 0 or 1. When p is 0, the two benzene rings to which the J group is bonded are directly connected.
According to some embodiments of aspects of the invention, in the general formula I, the COOA1、COOA2、COOA3、COOA4Respectively at ortho, para or meta positions relative to the ring N group. Preferably, the COOA1、COOA4In the meta or para position, respectively, of the N group on the ring.
According to some embodiments of aspects of the invention, in the general formula I, M is1、M6Respectively positioned at ortho-position, meta-position or para-position of NH group on the benzene ring.
According to some embodiments of the invention, the compound of formula I is one of the compounds represented by the following structural formulae:
the invention adopts another technical scheme that: the preparation method of the yellow brown reactive dye comprises the following steps:
(1) carrying out primary condensation reaction on a compound shown as a formula II and a compound shown as a formula III to obtain a condensate;
(2) carrying out secondary condensation reaction on the first condensate and a compound shown as a formula IV to obtain a second condensate;
(3) carrying out diazo reaction on the secondary condensate under the action of nitrous acid to obtain a first intermediate;
(4) carrying out primary coupling reaction on the first intermediate and a compound shown as a formula V to obtain a second intermediate;
(5) carrying out diazo reaction on the compound shown in the formula VI under the action of nitrous acid to obtain a third intermediate;
(6) carrying out secondary coupling reaction on the second intermediate and the third intermediate to obtain a fourth intermediate;
(7) carrying out diazo reaction on the compound shown in the formula VII under the action of nitrous acid to obtain a fifth intermediate;
(8) carrying out coupling reaction on the fifth intermediate and the fourth intermediate for three times to obtain a sixth intermediate;
(9) carrying out tertiary condensation reaction on the sixth intermediate and a compound shown as a formula VIII to obtain a reactive dye yellow brown of the compound shown as the formula I;
wherein,
R1、R2、R3each independently selected from H or an alkali metal cation;
j is selected from
P is selected from an integer between 0 and 3;
M1、M2、M3each independently selected from X, SO3X is alkyl with 1-5 carbon atoms or alkoxy with 1-5 carbon atoms, and X is H or alkali metal cation;
f is selected from Y, SO3Y、
Y is H or alkali metal cation, and m and n are respectively and independently selected from integers between 1 and 5;
A1、A2each independently selected from H or an alkali metal cation.
According to some embodiment aspects of the invention, F is selected from H, SO3H、SO3Na、SO3K、SO3Li、SO2C2H5、SO2C2H4Na、SO2C2H4K、SO2C2H4Li、SO2C2H4OSO3H、SO2C2H4OSO3Na、SO2C2H4OSO3K or SO2C2H4OSO3Li。
According to some embodiment aspects of the invention, the M1、M2、M3Each independently selected from H, SO3H、SO3Na、SO3K、SO3Li、CH3O or CH3. Preferably, said M1Selected from H, SO3H、SO3Na、SO3K or SO3Li。
According to some embodiment aspects of the invention, the alkali metal cation is Na, K or Li.
According to some embodiment aspects of the invention, in the step (1), the feeding molar ratio of the compound represented by the formula II to the compound represented by the formula III is 1: 0.98-1.02, and the primary condensation reaction is carried out at a pH value of 3.0-4.5 and a temperature of 0-15 ℃.
According to some embodiment aspects of the invention, in the step (2), the feeding molar ratio of the compound represented by the formula II to the compound represented by the formula IV is 1: 0.95-1.01, and the secondary condensation reaction is performed at a pH value of 4.5-6.0 and a temperature of 15-25 ℃.
According to some example aspects of the invention, step (3) is embodied as: and mixing the secondary condensate, hydrochloric acid, nitrite and water, and reacting at 0-15 ℃ to obtain the first intermediate, wherein the feeding molar ratio of the compound shown in the formula IV, HCl and nitrite ions is 1 (1.5-2.5) to 1.0-1.1.
According to some embodiment aspects of the invention, in the step (4), the feeding molar ratio of the compound shown as the formula IV to the compound shown as the formula V is 1: 0.95-1.0, and the primary coupling reaction is carried out at a pH value of 2.5-5.5 and a temperature of 10-20 ℃.
According to some example aspects of this invention, step (5) is embodied as: and mixing the compound shown in the formula VI, hydrochloric acid, nitrite and water, and reacting at 0-15 ℃ to obtain the third intermediate, wherein the feeding molar ratio of the compound shown in the formula VI, HCl and nitrite ions is 1 (1-2.5) to 1-1.1.
According to some embodiment aspects of the invention, in the step (6), the feeding of the second intermediate and the third intermediate is carried out according to the feeding molar ratio of the compound shown in the formula V to the compound shown in the formula VI of 1: 0.4-0.6, and the secondary coupling reaction is carried out at a pH value of 4.0-6.0 and a temperature of 10-20 ℃.
According to some example aspects of this invention, step (7) is embodied as: the compound shown in the formula VII, hydrochloric acid, nitrite and water are mixed and react at the temperature of 0-15 ℃, wherein the feeding molar ratio of the compound shown in the formula VII, HCl and nitrite ions is 1 (1-2.5) to 1-1.1.
According to some embodiment aspects of the invention, in the step (8), the fourth intermediate and the fifth intermediate are fed according to a feeding molar ratio of the compound shown in the formula V to the compound shown in the formula VII of 1: 0.98-1.02, and the third condensation reaction is carried out at a pH value of 4.0-6.0 and a temperature of 10-20 ℃.
According to some embodiment aspects of the invention, in the step (9), the feeding molar ratio of the compound represented by the formula II to the compound represented by the formula VIII is 1: 2.0-3.5, and the three-time condensation reaction is carried out at a pH value of 5.0-7.0 and a temperature of 75-90 ℃.
According to some example aspects of the invention, the method of making is embodied by the steps of:
(1) mixing the compound shown in the formula II, ice water and the compound shown in the formula III, adding weak base to adjust the pH value to 3.0-4.5, and then stirring and reacting for 2-4 h at 0-15 ℃ to obtain a first reaction liquid, wherein the weak base is one or more of sodium bicarbonate, lithium bicarbonate and potassium bicarbonate;
(2) adding the compound shown in the formula IV into the first reaction liquid, adding a weak base to adjust the pH value of the system to be 4.5-6.0, and stirring and reacting for 4-6 h at 15-25 ℃ to obtain a second reaction liquid, wherein the weak base is one or more of sodium bicarbonate, lithium bicarbonate and potassium bicarbonate;
(3) adding hydrochloric acid and sodium nitrite into the second reaction solution, and stirring and reacting for 1-3 hours at 0-15 ℃ to obtain a third reaction solution;
(4) adding the compound shown in the formula V into the third reaction liquid, adding weak base to adjust the pH value to 2.5-5.5, and stirring and reacting for 3-5 h at 10-20 ℃ to obtain a fourth reaction liquid, wherein the weak base is one or more of sodium bicarbonate, lithium bicarbonate and potassium bicarbonate;
(5) mixing the compound shown in the formula VI, hydrochloric acid, sodium nitrite and ice water, and reacting for 1-3 hours at 0-15 ℃ to obtain a fifth reaction solution;
(6) mixing the fifth reaction solution and the fourth reaction solution, adding weak base to adjust the pH value to 4.0-6.0, and stirring and reacting at 10-20 ℃ for 4-6 h to obtain a sixth reaction solution, wherein the weak base is one or more of sodium bicarbonate, lithium bicarbonate and potassium bicarbonate;
(7) mixing the compound shown in the formula VII, hydrochloric acid, sodium nitrite and ice water, and reacting for 1-3 hours at 0-15 ℃ to obtain a seventh reaction solution;
(8) mixing the seventh reaction liquid and the sixth reaction liquid, adding weak base to adjust the pH value to 4.0-6.0, and stirring and reacting for 2-4 hours at 10-20 ℃ to obtain an eighth reaction liquid, wherein the weak base is one or more of sodium bicarbonate, lithium bicarbonate and potassium bicarbonate;
(9) adding the compound shown in the formula VIII into the eighth reaction liquid, adding strong base to adjust the pH value to 5.0-7.0, and reacting at 75-90 ℃ for 6-9 hours to obtain a ninth reaction liquid;
(10) and drying the ninth reaction solution to obtain the reactive dye yellow brown.
According to some example aspects of the present invention, in the step (6), the fourth reaction solution and the fifth reaction solution are fed according to a feeding molar ratio of the compound represented by the formula V to the compound represented by the formula VI of 1: 0.4-0.6.
According to some example aspects of the present invention, in the step (8), the sixth reaction solution and the seventh reaction solution are fed according to a feeding molar ratio of the compound represented by the formula V to the compound represented by the formula VII of 1: 0.98-1.02.
According to another technical scheme adopted by the invention, the reactive dye yellow brown is applied to pure cotton, rayon, T/R or T/C blended fabrics.
When the reactive dye yellow brown is used for dyeing pure cotton (or rayon), the reactive dye yellow brown and anhydrous sodium sulphate are dissolved in water, the temperature is increased to 100-130 ℃, and the pure cotton (or rayon) is subjected to heat preservation dyeing, cooling, water washing and soaping.
The addition amount of the reactive dye yellow brown and the anhydrous sodium sulphate can be added according to the addition amount of the existing reactive dye and anhydrous sodium sulphate, and the heat preservation is usually 20-60 min. Such as about 40 min.
Due to the application of the technical scheme, compared with the prior art, the invention has the following advantages:
the reactive dye has higher reactivity, good color fixing capability and good dyeing capability, and the reactive dye does not need to be added with soda for color fixing during dyeing, so that the use of the soda is avoided. Meanwhile, the reactive dye also has high temperature resistance, can be used in cooperation with a disperse dye, and can be used for dyeing a polyester-cotton product at the temperature of 100 ℃ or higher, so that a one-bath dyeing process is realized, the dyeing process is simplified, the dyeing time is shortened, the discharge capacity is greatly reduced, and the labor cost and the energy consumption are reduced.
Detailed Description
In order to make the objects, technical solutions and effects of the present invention clearer and clearer, the present invention is described in further detail below. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
In the following examples, each raw material was commercially available, and hydrochloric acid having a concentration of 30% was used.
Example 1
The reactive dye yellow brown provided in this example is prepared by the following method:
(1) will be provided with
Adding into crushed ice and water, stirring
The mixture is added into the reactor,adding sodium bicarbonate to adjust the pH value to 3.0-3.5, reacting for 3.5h at the temperature of 5-10 ℃ to obtain a first mixed solution, wherein,
and
the feeding molar ratio of (A) to (B) is 1: 0.99;
(2) will be provided with
Adding the mixture into the first mixed solution, adding sodium bicarbonate to adjust the pH value to 5.5-6.0, reacting for 5.5h at the temperature of 20-25 ℃ to obtain a second mixed solution, wherein,
and
the feeding molar ratio of (1: 0.96);
(3) adding hydrochloric acid and sodium nitrite into the second mixed solution, reacting for 1.5h at 0-5 ℃ to obtain a third mixed solution, wherein,
the feeding molar ratio of HCl to sodium nitrite is 1:2.0: 1.0;
(4) will be provided with
Adding the mixture into the third mixed solution, adding sodium bicarbonate to adjust the pH value to 4.0-4.5, reacting for 4.5 hours at the temperature of 10-15 ℃ to obtain a fourth mixed solution, wherein,
and
the feeding molar ratio of (A) to (B) is 1: 1.0;
(5) will be provided with
Adding the mixture into water and crushed ice, stirring, keeping the temperature at 0-5 ℃, adding a hydrochloric acid solution, adding a sodium nitrite solution, reacting for 1.5 hours to obtain a fifth mixed solution, wherein,
the feeding molar ratio of HCl to sodium nitrite is 1:1.0: 1.0;
(6) adding the fifth mixed solution into the fourth mixed solution, adding sodium bicarbonate to adjust the pH value to 5.5-6.0, and reacting at 10-15 ℃ for 5-6 h to obtain a sixth mixed solution, wherein the feeding of the fourth mixed solution and the fifth mixed solution is carried out according to the proportion
And
the feeding molar ratio of (1: 0.49) is carried out;
(7) will be provided with
Adding the mixed solution into water and crushed ice, stirring, keeping the temperature at 10-15 ℃, adding a hydrochloric acid solution, adding a sodium nitrite solution, reacting for 1h to obtain a seventh mixed solution, wherein,
the feeding molar ratio of HCl to sodium nitrite is 1:1.0: 1.01;
(8) adding the seventh mixed solution into the sixth mixed solution, adding sodium bicarbonate to adjust the pH value to 5.5-6.0, and reacting for 2.5 hours at 15-20 ℃ to obtain an eighth mixed solution, wherein the feeding of the sixth mixed solution and the seventh mixed solution is carried out according to the proportion
And
the feeding molar ratio of (1: 1.02) is carried out;
(9) will be provided with
Adding the mixture into the eighth mixed solution, adding sodium carbonate to adjust the pH value to 5.5-6.0, reacting for 7 hours at the temperature of 75-80 ℃ to obtain a ninth mixed solution, wherein,
and
the feeding molar ratio of (1: 2.5);
(10) and drying the ninth mixed solution.
The product has the following structural formula:
example 2
The reactive dye yellow brown provided in this example is prepared by the following method:
(1) will be provided with
Adding into crushed ice and water, stirring
Adding the mixture, adding sodium bicarbonate to adjust the pH value to 3.0-3.5, reacting for 3 hours at the temperature of 5-10 ℃ to obtain a first mixed solution, wherein,
and
the feeding molar ratio of (A) to (B) is 1: 0.99;
(2) will be provided with
Adding into the first mixed solution, and adding carbonic acidAdjusting the pH value to 5.5-6.0 with sodium bicarbonate, reacting for 6h at 20-25 ℃ to obtain a second mixed solution, wherein,
and
the feeding molar ratio of (1: 0.96);
(3) adding hydrochloric acid and sodium nitrite into the second mixed solution, reacting for 1.5h at 0-5 ℃ to obtain a third mixed solution, wherein,
the feeding molar ratio of HCl to sodium nitrite is 1:2.0: 1.0;
(4) will be provided with
Adding the mixture into the third mixed solution, adding sodium bicarbonate to adjust the pH value to 4.0-4.5, reacting for 5 hours at the temperature of 10-15 ℃ to obtain a fourth mixed solution, wherein,
and
the feeding molar ratio of (A) to (B) is 1: 1.0;
(5) will be provided with
Adding the mixture into water and crushed ice, stirring, keeping the temperature at 0-5 ℃, adding a hydrochloric acid solution, adding a sodium nitrite solution, reacting for 1.5 hours to obtain a fifth mixed solution, wherein,
the feeding molar ratio of HCl to sodium nitrite is 1:1.0: 1.1;
(6) adding the fifth mixed solution into the fourth mixed solution, adding sodium bicarbonate to adjust the pH value to 5.5-6.0, and reacting for 5 hours at 10-15 ℃ to obtain a sixth mixed solution, wherein the fourth mixed solution and the fourth mixed solutionThe fifth mixed solution is fed according to
And
the feeding molar ratio of (1: 0.5) is carried out;
(7) will be provided with
Adding the mixed solution into water and crushed ice, stirring, keeping the temperature at 0-5 ℃, adding a hydrochloric acid solution, adding a sodium nitrite solution, reacting for 1h to obtain a seventh mixed solution, wherein,
the feeding molar ratio of HCl to sodium nitrite is 1:1.0: 1.01;
(8) adding the seventh mixed solution into the sixth mixed solution, adding sodium bicarbonate to adjust the pH value to 5.5-6.0, and reacting for 3 hours at 15-20 ℃ to obtain an eighth mixed solution, wherein the feeding of the sixth mixed solution and the seventh mixed solution is carried out according to the proportion
And
the feeding molar ratio of (1: 1.02) is carried out;
(9) will be provided with
Adding the mixture into the eighth mixed solution, adding sodium carbonate to adjust the pH value to 5.5-6.0, reacting for 7 hours at the temperature of 75-80 ℃ to obtain a ninth mixed solution, wherein,
and
the feeding molar ratio of (1: 2.5);
(10) and drying the ninth mixed solution.
The structural formula of the product is as follows:
example 3
The reactive dye yellow brown provided in this example is prepared by the following method:
(1) will be provided with
Adding into crushed ice and water, stirring
Adding the mixture, adding sodium bicarbonate to adjust the pH value to 3.0-3.5, reacting for 4 hours at the temperature of 5-10 ℃ to obtain a first mixed solution, wherein,
and
the feeding molar ratio of (A) to (B) is 1: 0.99;
(2) will be provided with
Adding the mixture into the first mixed solution, adding sodium bicarbonate to adjust the pH value to 5.5-6.0, reacting for 6 hours at the temperature of 20-25 ℃ to obtain a second mixed solution, wherein,
and
the feeding molar ratio of (1: 0.96);
(3) adding hydrochloric acid and sodium nitrite into the second mixed solution, reacting for 1.5h at 0-5 ℃ to obtain a third mixed solution, wherein,
the feeding molar ratio of HCl to sodium nitrite is 1:2.0: 1.0;
(4) will be provided with
Adding the mixture into the third mixed solution, adding sodium bicarbonate to adjust the pH value to 4.0-4.5, reacting for 4 hours at the temperature of 10-15 ℃ to obtain a fourth mixed solution, wherein,
and
the feeding molar ratio of (1: 0.98);
(5) will be provided with
Adding the mixture into water and crushed ice, stirring, keeping the temperature at 0-5 ℃, adding a hydrochloric acid solution, adding a sodium nitrite solution, reacting for 1.5 hours to obtain a fifth mixed solution, wherein,
the feeding molar ratio of HCl to sodium nitrite is 1:1.0: 1.0;
(6) adding the fifth mixed solution into the fourth mixed solution, adding sodium bicarbonate to adjust the pH value to 5.5-6.0, and reacting for 5 hours at 10-15 ℃ to obtain a sixth mixed solution, wherein the feeding of the fourth mixed solution and the fifth mixed solution is carried out according to the proportion
And
the feeding molar ratio of (1: 0.51) is carried out;
(7) will be provided with
Adding the mixture into water and crushed ice, stirring, keeping the temperature at 0-5 ℃, adding a hydrochloric acid solution, and adding a sodium nitrite solution for reactionObtaining a seventh mixed solution within 1h, wherein,
the feeding molar ratio of HCl to sodium nitrite is 1:1.0: 1.01;
(8) adding the seventh mixed solution into the sixth mixed solution, adding sodium bicarbonate to adjust the pH value to 5.5-6.0, and reacting for 3 hours at 15-20 ℃ to obtain an eighth mixed solution, wherein the feeding of the sixth mixed solution and the seventh mixed solution is carried out according to the proportion
And
the feeding molar ratio of (1: 1.02) is carried out;
(9) will be provided with
Adding the mixture into the eighth mixed solution, adding sodium carbonate to adjust the pH value to 5.5-6.0, reacting for 7 hours at the temperature of 75-80 ℃ to obtain a ninth mixed solution, wherein,
and
the feeding molar ratio of (1: 2.5);
(10) and drying the ninth mixed solution.
The product has the following structural formula:
example 4
The reactive dye yellow brown provided in this example is prepared by the following method:
(1) will be provided with
Adding into the powderStirring in ice and water, mixing
Adding the mixture, adding sodium bicarbonate to adjust the pH value to 3.0-3.5, reacting for 3 hours at the temperature of 5-10 ℃ to obtain a first mixed solution, wherein,
and
the feeding molar ratio of (A) to (B) is 1: 0.99;
(2) will be provided with
Adding the mixture into the first mixed solution, adding sodium bicarbonate to adjust the pH value to 5.5-6.0, reacting for 5 hours at the temperature of 20-25 ℃ to obtain a second mixed solution, wherein,
and
the feeding molar ratio of (1: 0.96);
(3) adding hydrochloric acid and sodium nitrite into the second mixed solution, reacting for 1.5h at 0-5 ℃ to obtain a third mixed solution, wherein,
the feeding molar ratio of HCl to sodium nitrite is 1:2.0: 1.1;
(4) will be provided with
Adding the mixture into the third mixed solution, adding sodium bicarbonate to adjust the pH value to 4.0-4.5, reacting for 5 hours at the temperature of 10-15 ℃ to obtain a fourth mixed solution, wherein,
and
the feeding molar ratio of (A) to (B) is 1: 1.0;
(5) will be provided with
Adding the mixture into water and crushed ice, stirring, keeping the temperature at 0-5 ℃, adding a hydrochloric acid solution, adding a sodium nitrite solution, reacting for 1.5 hours to obtain a fifth mixed solution, wherein,
the feeding molar ratio of HCl to sodium nitrite is 1:1.0: 1.0;
(6) adding the fifth mixed solution into the fourth mixed solution, adding sodium bicarbonate to adjust the pH value to 5.5-6.0, and reacting for 5.5 hours at 10-15 ℃ to obtain a sixth mixed solution, wherein the feeding of the fourth mixed solution and the fifth mixed solution is carried out according to the proportion
And
the feeding molar ratio of (1: 0.51) is carried out;
(7) will be provided with
Adding the mixed solution into water and crushed ice, stirring, keeping the temperature at 0-5 ℃, adding a hydrochloric acid solution, adding a sodium nitrite solution, reacting for 1h to obtain a seventh mixed solution, wherein,
the feeding molar ratio of HCl to sodium nitrite is 1:1.0: 1.01;
(8) adding the seventh mixed solution into the sixth mixed solution, adding sodium bicarbonate to adjust the pH value to 5.5-6.0, and reacting for 3 hours at 15-20 ℃ to obtain an eighth mixed solution, wherein the feeding of the sixth mixed solution and the seventh mixed solution is carried out according to the proportion
And
the feeding molar ratio of (1: 1.02) is carried out;
(9) will be provided with
Adding the mixture into the eighth mixed solution, adding sodium carbonate to adjust the pH value to 5.5-6.0, reacting for 6 hours at the temperature of 75-80 ℃ to obtain a ninth mixed solution, wherein,
and
the feeding molar ratio of (1: 2.5);
(10) and drying the ninth mixed solution.
The product has the following structural formula:
comparative example 1
The commercially available reactive dye is yellow brown, and the structural formula is as follows:
performance testing
1. Preparation of dyeing liquor
The reactive dyes of examples 1-4 and comparative example 1 were mixed according to the dyeing depth of 2% o.w.f, the anhydrous sodium sulphate dosage of 60g/l, the bath ratio of 1: 10, preparing each dyeing solution for later use.
2. Dyeing process (pure cotton)
The dyeing process using the dyeing solutions of examples 1 to 4 comprises: the dyeing liquid prepared by the reactive dyes of the embodiments 1 to 4 is heated, and pure cotton is dyed, washed and soaped, so that dyeing is completed.
Dyeing process using the dyeing liquor of comparative example 1: the dyeing liquid prepared by the reactive dye of the comparative example 1 is heated, and the sodium carbonate (the dosage is 20g/l) is added to dye, wash and soap the pure cotton, thus completing the dyeing.
3. Optimal coloring temperature determination
The dyeing solutions prepared by using the reactive dyes of example 1 and comparative example 1 were used to dye 12 cotton pieces of the same color at 60 ℃, 80 ℃, 100 ℃, 110 ℃, 120 ℃ and 130 ℃ respectively according to the above dyeing process, the color yields of the 12 dyed cotton pieces were measured respectively, and the relative color yields of the cotton pieces at 60 ℃, 80 ℃, 100 ℃, 110 ℃ and 120 ℃ were calculated respectively using the color yields at 130 ℃ as a reference standard, and the results are shown in table 1.
Table 1 shows the comparison of the optimum coloring temperatures of the reactive dye of example 1 with the reactive dye of comparative example 1
As can be seen from Table 1, the optimum coloring temperature of the reactive dye of example 1 is 100-130 ℃.
The dyeing liquid prepared by the active dyes of the embodiments 2 to 4 is used for dyeing different pure cotton with the same color at the temperature of 60 ℃, 80 ℃, 100 ℃, 110 ℃, 120 ℃ and 130 ℃, and the finally obtained optimal coloring temperature is also 100 to 130 ℃.
As can be seen from the above, the reactive dyes of examples 1 to 4 of the present invention have an optimum dyeing temperature of 100 to 130 ℃ which is the same as the dyeing temperature (110 to 130 ℃) of the disperse dye, and can be mixed with the disperse dye to perform one-bath dyeing. In addition, the reactive dyes of the embodiments 1 to 4 of the invention do not need to be added with soda ash for color fixation when being dyed.
The best coloring temperature of the existing common reactive dye is about 60 ℃, the dye cannot be simultaneously dyed with the disperse dye in one bath, and sodium carbonate is added for fixation during dyeing, so that the dyeing cost is increased, and the sewage and sludge treatment cost is also increased.
4. Testing of light resistance, wash resistance, perspiration resistance, friction resistance, hot press resistance, solubility
1) Respectively heating the dyeing solution prepared by the reactive dyes in the embodiments 1-4 to 100 ℃, carrying out heat preservation on pure cotton for 40min for dyeing, cooling, washing and soaping, and finishing dyeing.
2) The dyeing liquid prepared by the reactive dye of the comparative example 1 is heated to 60 ℃, pure cotton is dyed, sodium carbonate (20g/l) is added for fixation, the temperature is kept for 40min, and the dyeing is finished after cooling, washing and soaping.
The dyed pure cotton cloth was subjected to performance test, and the results are shown in table 2.
Table 2 shows the performance test of the reactive dyes yellow brown of examples 1 to 4 and comparative example 1
As can be seen from Table 2, the reactive dyes of examples 1 to 4 of the present invention have the same or better fastness than the conventional reactive dyes at 60 ℃ when dyed at a high temperature of 100 ℃. As is clear from the above Table 1, the dyeing properties of the conventional reactive dyes are poor when the dyes are dyed at a high temperature of 100 ℃.
The above performance tests were performed using the following criteria:
1) color fastness to rubbing: GB/T3920-
2) Color fastness to perspiration: GB/T3922-
3) Color fastness to light: GB/T8427. 2008. method 3
4) Color fastness to washing: GB/T3921-
5) Heat resistance at 200 ℃: GB/T6152-1997.
6) Solubility: GB/T21879-2015.
5. Polyester cotton one-bath dyeing
At room temperature, the reactive dye of example 1 was dyed at a depth of 2% o.w.f, the commercially available disperse dye yellow brown T-DW (wujiang peach-derived dye) at a depth of 0.96o.w.f, anhydrous sodium sulphate 60g/l, bath ratio 1: 10 preparing a staining solution. Heating the dyeing solution to 110-.
The result shows that the cloth surface color is full when the yellow brown T-DW dye of the example 1 and the disperse dye are dyed in one bath, and the polyester and cotton dyeing has no color difference, thereby achieving the effect of dyeing in two baths.
The above embodiments are merely illustrative of the technical ideas and features of the present invention, and the purpose thereof is to enable those skilled in the art to understand the contents of the present invention and implement the present invention, and not to limit the protection scope of the present invention. All equivalent changes and modifications made according to the spirit of the present invention should be covered within the protection scope of the present invention.
The endpoints of the ranges and any values disclosed herein are not limited to the precise range or value, and such ranges or values should be understood to encompass values close to those ranges or values. For ranges of values, between the endpoints of each of the ranges and the individual points, and between the individual points may be combined with each other to give one or more new ranges of values, and these ranges of values should be considered as specifically disclosed herein.
Claims (10)
1. A yellow brown reactive dye is characterized in that: the structure of the yellow brown reactive dye compound is shown as a general formula I:
in the formula:
R1、R2、R3、R4each independently selected from H or an alkali metal cation;
j is selected from
P is selected from an integer between 0 and 3;
F1、F2each independently selected from H, SO3Y1Or
Said Y is1Is H or alkali metal cation, and m is an integer between 1 and 5;
M1、M2、M3、M4、M5、M6each independently selected from H, SO3Y2An alkyl group having 1 to 5 carbon atoms or an alkoxy group having 1 to 5 carbon atoms, Y2Is H or an alkali metal cation;
A1、A2、A3、A4each independently selected from H or an alkali metal cation.
2. The reactive dye yellow brown according to claim 1, characterized in that: the alkali metal cation is Na, K or Li.
3. The reactive dye yellow brown according to claim 1, characterized in that: said F1、F2Each independently selected from H, SO3H、SO3Na、SO3K、SO3Li、SO2C2H4OSO3H、SO2C2H4OSO3Na、SO2C2H4OSO3K or SO2C2H4OSO3Li; the M is1、M2、M3、M4、M5、M6Each independently selected from H, SO3H、SO3Na、SO3K、SO3Li、CH3O or CH3。
4. The reactive dye yellow brown according to claim 1, characterized in that: and p is 0 or 1.
5. The reactive dye yellow brown according to claim 1, characterized in that: the compound shown in the general formula I is one of the compounds shown in the following structural formula:
6. a method for preparing yellow brown reactive dye according to any one of claims 1 to 5, wherein the yellow brown reactive dye comprises the following components: the preparation method comprises the following steps:
(1) carrying out primary condensation reaction on a compound shown as a formula II and a compound shown as a formula III to obtain a condensate;
(2) carrying out secondary condensation reaction on the first condensate and a compound shown as a formula IV to obtain a second condensate;
(3) carrying out diazo reaction on the secondary condensate under the action of nitrous acid to obtain a first intermediate;
(4) carrying out primary coupling reaction on the first intermediate and a compound shown as a formula V to obtain a second intermediate;
(5) carrying out diazo reaction on the compound shown in the formula VI under the action of nitrous acid to obtain a third intermediate;
(6) carrying out secondary coupling reaction on the second intermediate and the third intermediate to obtain a fourth intermediate;
(7) carrying out diazo reaction on the compound shown in the formula VII under the action of nitrous acid to obtain a fifth intermediate;
(8) carrying out coupling reaction on the fifth intermediate and the fourth intermediate for three times to obtain a sixth intermediate;
(9) carrying out tertiary condensation reaction on the sixth intermediate and a compound shown as a formula VIII to obtain a reactive dye yellow brown of the compound shown as the formula I;
wherein,
R1、R2、R3each independently selected from H or an alkali metal cation;
j is selected from
P is selected from an integer between 0 and 3;
M1、M2、M3each independently selected from H, SO3X is alkyl with 1-5 carbon atoms or alkoxy with 1-5 carbon atoms, and X is H or alkali metal cation;
f is selected from H, SO3Y、
Y is H or alkali metal cation, and m is an integer between 1 and 5;
A1、A2each independently selected from H or an alkali metal cation.
7. The method of claim 6, wherein: f is selected from H, SO3H、SO3Na、SO3K、SO3Li、SO2C2H4OSO3H、SO2C2H4OSO3Na、SO2C2H4OSO3K or SO2C2H4OSO3Li; the M is1、M2、M3Each independently selected from H, SO3H、SO3Na、SO3K、SO3Li、CH3O or CH3(ii) a The alkali metal cation is Na, K or Li.
8. The method of claim 6, wherein: in the step (1), the feeding molar ratio of the compound shown in the formula II to the compound shown in the formula III is 1: 0.98-1.02, and the primary condensation reaction is carried out at a pH value of 3.0-4.5 and a temperature of 0-15 ℃; in the step (2), the feeding molar ratio of the compound shown in the formula II to the compound shown in the formula IV is 1: 0.95-1.01, and the secondary condensation reaction is carried out at a pH value of 4.5-6.0 and a temperature of 15-25 ℃; the specific implementation of the step (3) is as follows: mixing the secondary condensate, hydrochloric acid, nitrite and water, and reacting at 0-15 ℃ to obtain the first intermediate, wherein the feeding molar ratio of the compound shown in the formula IV, HCl and nitrite ions is 1 (1.5-2.5) to 1.0-1.1; step (4), the feeding molar ratio of the compound shown in the formula IV to the compound shown in the formula V is 1: 0.95-1.0, and the primary coupling reaction is carried out at a pH value of 2.5-5.5 and a temperature of 10-20 ℃; the specific implementation of the step (5) is as follows: mixing the compound shown in the formula VI, hydrochloric acid, nitrite and water, and reacting at 0-15 ℃ to obtain the third intermediate, wherein the feeding molar ratio of the compound shown in the formula VI, HCl and nitrite ions is 1 (1-2.5) to 1-1.1; in the step (6), feeding the second intermediate and the third intermediate according to the feeding molar ratio of the compound shown in the formula V to the compound shown in the formula VI of 1: 0.4-0.6, and carrying out secondary coupling reaction at the pH value of 4.0-6.0 and the temperature of 10-20 ℃; the specific implementation of the step (7) is as follows: mixing the compound shown in the formula VII, hydrochloric acid, nitrite and water, and reacting at 0-15 ℃, wherein the feeding molar ratio of the compound shown in the formula VII, HCl and nitrite ions is 1 (1-2.5) to 1-1.1; in the step (8), feeding the fourth intermediate and the fifth intermediate according to the feeding molar ratio of the compound shown in the formula V to the compound shown in the formula VII of 1: 0.98-1.02, wherein the third condensation reaction is carried out at the pH value of 4.0-6.0 and the temperature of 10-20 ℃; in the step (9), the feeding molar ratio of the compound shown in the formula II to the compound shown in the formula VIII is 1: 2.0-3.5, and the tertiary condensation reaction is carried out at a pH value of 5.0-7.0 and a temperature of 75-90 ℃.
9. The method of claim 6, wherein: the specific implementation of the preparation method comprises the following steps:
(1) mixing the compound shown in the formula II, ice water and the compound shown in the formula III, adding weak base to adjust the pH value to 3.0-4.5, and then stirring and reacting for 2-4 h at 0-15 ℃ to obtain a first reaction liquid, wherein the weak base is one or more of sodium bicarbonate, lithium bicarbonate and potassium bicarbonate;
(2) adding the compound shown in the formula IV into the first reaction liquid, adding a weak base to adjust the pH value of the system to be 4.5-6.0, and stirring and reacting for 4-6 h at 15-25 ℃ to obtain a second reaction liquid, wherein the weak base is one or more of sodium bicarbonate, lithium bicarbonate and potassium bicarbonate;
(3) adding hydrochloric acid and sodium nitrite into the second reaction solution, and stirring and reacting for 1-3 hours at 0-15 ℃ to obtain a third reaction solution;
(4) adding the compound shown in the formula V into the third reaction liquid, adding weak base to adjust the pH value to 2.5-5.5, and stirring and reacting for 3-5 h at 10-20 ℃ to obtain a fourth reaction liquid, wherein the weak base is one or more of sodium bicarbonate, lithium bicarbonate and potassium bicarbonate;
(5) mixing the compound shown in the formula VI, hydrochloric acid, sodium nitrite and ice water, and reacting for 1-3 hours at 0-15 ℃ to obtain a fifth reaction solution;
(6) mixing the fifth reaction solution and the fourth reaction solution, adding weak base to adjust the pH value to 4.0-6.0, and stirring and reacting at 10-20 ℃ for 4-6 h to obtain a sixth reaction solution, wherein the weak base is one or more of sodium bicarbonate, lithium bicarbonate and potassium bicarbonate;
(7) mixing the compound shown in the formula VII, hydrochloric acid, sodium nitrite and ice water, and reacting for 1-3 hours at 0-15 ℃ to obtain a seventh reaction solution;
(8) mixing the seventh reaction liquid and the sixth reaction liquid, adding weak base to adjust the pH value to 4.0-6.0, and stirring and reacting for 2-4 hours at 10-20 ℃ to obtain an eighth reaction liquid, wherein the weak base is one or more of sodium bicarbonate, lithium bicarbonate and potassium bicarbonate;
(9) adding the compound shown in the formula VIII into the eighth reaction liquid, adding strong base to adjust the pH value to 5.0-7.0, and reacting at 75-90 ℃ for 6-9 hours to obtain a ninth reaction liquid;
(10) and drying the ninth reaction solution to obtain the reactive dye yellow brown.
10. Use of the reactive dye yellow brown according to any one of claims 1 to 5 in pure cotton, rayon, T/R or T/C blended fabrics.
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| CN104371356A (en) * | 2014-09-29 | 2015-02-25 | 浙江亿得化工有限公司 | Low-alkali or alkali-free active bright yellow dye and preparation method thereof |
| CN104830097A (en) * | 2015-04-13 | 2015-08-12 | 浙江亿得化工有限公司 | Yellowish-brown reactive dye and preparation method thereof |
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| CN104371356A (en) * | 2014-09-29 | 2015-02-25 | 浙江亿得化工有限公司 | Low-alkali or alkali-free active bright yellow dye and preparation method thereof |
| CN104830097A (en) * | 2015-04-13 | 2015-08-12 | 浙江亿得化工有限公司 | Yellowish-brown reactive dye and preparation method thereof |
Non-Patent Citations (1)
| Title |
|---|
| Serological properties of simple substances. I. Precipitation reactions between antibodies and substances containing two or more haptenic groups;Pauling, Linus等;《Journal of the American Chemical Society》;19421231;第64卷;2994-3003 * |
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