CN115594987A - Acid orange disazo dye and preparation method thereof - Google Patents
Acid orange disazo dye and preparation method thereof Download PDFInfo
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- CN115594987A CN115594987A CN202211189438.XA CN202211189438A CN115594987A CN 115594987 A CN115594987 A CN 115594987A CN 202211189438 A CN202211189438 A CN 202211189438A CN 115594987 A CN115594987 A CN 115594987A
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- diphenylcyclohexane
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- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- 238000005859 coupling reaction Methods 0.000 claims abstract description 49
- 230000008878 coupling Effects 0.000 claims abstract description 48
- 238000010168 coupling process Methods 0.000 claims abstract description 48
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 24
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims abstract description 24
- 239000012954 diazonium Substances 0.000 claims abstract description 18
- 150000001989 diazonium salts Chemical class 0.000 claims abstract description 16
- 235000010288 sodium nitrite Nutrition 0.000 claims abstract description 12
- 150000001875 compounds Chemical class 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 7
- 238000001035 drying Methods 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 5
- 238000006193 diazotization reaction Methods 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 238000005185 salting out Methods 0.000 claims description 4
- 230000032050 esterification Effects 0.000 claims description 3
- 238000005886 esterification reaction Methods 0.000 claims description 3
- 238000004806 packaging method and process Methods 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims 5
- 238000004043 dyeing Methods 0.000 abstract description 16
- 239000004744 fabric Substances 0.000 abstract description 10
- 230000000694 effects Effects 0.000 abstract description 4
- 239000002253 acid Substances 0.000 abstract description 3
- 230000001988 toxicity Effects 0.000 abstract description 3
- 231100000419 toxicity Toxicity 0.000 abstract description 3
- 239000000975 dye Substances 0.000 description 34
- 239000000243 solution Substances 0.000 description 26
- 239000000047 product Substances 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
- 239000000980 acid dye Substances 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 229920006052 Chinlon® Polymers 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- SJEYSFABYSGQBG-UHFFFAOYSA-M Patent blue Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 SJEYSFABYSGQBG-UHFFFAOYSA-M 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 235000017550 sodium carbonate Nutrition 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000012085 test solution Substances 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- -1 4,4' -diaminotriphenylmethane diazonium salt Chemical class 0.000 description 1
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 1
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229920004933 Terylene® Polymers 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 235000009120 camo Nutrition 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 235000005607 chanvre indien Nutrition 0.000 description 1
- IQFVPQOLBLOTPF-HKXUKFGYSA-L congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000983 mordant dye Substances 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- IAAKNVCARVEIFS-UHFFFAOYSA-M sodium;4-hydroxynaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(O)=CC=C(S([O-])(=O)=O)C2=C1 IAAKNVCARVEIFS-UHFFFAOYSA-M 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Images
Classifications
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- 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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/18—Preparation of azo dyes from other azo compounds by acylation of hydroxyl group or of mercapto group
- C09B43/20—Preparation of azo dyes from other azo compounds by acylation of hydroxyl group or of mercapto group with monocarboxylic acids, carbamic acid esters or halides, mono- isocyanates or haloformic acid esters
- C09B43/202—Aliphatic, cycloaliphatic, araliphatic carboxylic acids
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
The invention relates to the technical field of chemistry, in particular to an acid orange disazo dye and a preparation method thereof, which comprises the steps of diazotizing a 4,4 '-diamino-1, 1' -diphenylcyclohexane compound in the environment of sodium nitrite and hydrochloric acid to obtain a diazonium salt of the 4,4 '-diamino-1, 1' -diphenylcyclohexane compound; coupling the diazonium salt of the 4,4 '-diamino-1, 1' -diphenylcyclohexane compound twice and then esterifying to obtain a coupling product solution; and carrying out post-treatment on the coupling product solution to obtain the acid orange disazo dye. The acid orange disazo dye can be dyed under an acid condition, and has bright color, good lifting power, high solubility, good leveling property and high color fastness during dyeing. In addition, the acid orange disazo dye is safe and low in toxicity. Solves the problem of poor dyeing effect of the existing dye on the fabric.
Description
Technical Field
The invention relates to the technical field of chemistry, in particular to an acid orange disazo dye and a preparation method thereof.
Background
Dyes that dye in an acidic medium are referred to as acid dyes. The acid dye is usually sulfonate, but a few carboxylate, can be dissolved in water, has bright color, is mainly used for dyeing and printing wool, leather, silk, chinlon, polyamide fiber and the like, and is also used for dyeing food and paper. Acid dyes can be classified into strongly acidic dyes, weakly acidic dyes, and neutral mordant dyes according to their chemical structures and dyeing conditions.
The strong acid dye is developed at the earliest time, is required to be dyed in a strong acid dye bath, has a simple molecular structure and low relative molecular mass, and can be uniformly dyed. However, strongly acidic dyes do not give good wet fastness because of the high damage to the fabric during dyeing. Neutral medium dye has good light fastness but poor dyeing brilliance, and has poor effect of reducing the dyeing of fabrics.
Disclosure of Invention
The invention aims to provide an acid orange disazo dye and a preparation method thereof, and aims to solve the problem that the existing dye has poor dyeing effect on fabrics.
In order to achieve the above object, in a first aspect, the present invention provides a method for preparing an acid orange disazo dye, comprising the steps of:
diazotizing 4,4 '-diamino-1, 1' -diphenylcyclohexane compounds in the environment of sodium nitrite and hydrochloric acid to obtain diazonium salt of the 4,4 '-diamino-1, 1' -diphenylcyclohexane compounds;
performing coupling twice on the diazonium salt of the 4,4 '-diamino-1, 1' -diphenylcyclohexane compound, and then performing esterification to obtain a coupling product solution;
and carrying out post-treatment on the coupling product solution to obtain the acid orange disazo dye.
Wherein the molar ratio of the 4,4 '-diamino-1, 1' -diphenylcyclohexane compound, the hydrochloric acid and the sodium nitrite is 1:4-6:2.0-2.05.
Wherein the diazotization reaction is carried out at 0-5 ℃.
Wherein, the diazo salt of the 4,4 '-diamino-1, 1' -diphenylcyclohexane compound is esterified after being coupled twice, so as to obtain a coupling product solution, which comprises:
coupling the diazonium salt of the 4,4 '-diamino-1, 1' -diphenylcyclohexane compound with a first compound at 3-5 ℃ to obtain a primary coupling product;
coupling the primary coupling product with a second compound at 5-8 ℃ to obtain a secondary coupling product;
and (3) esterifying the secondary coupling product and a third compound at 68-75 ℃ to obtain a coupling product solution.
Wherein the molar ratio of the first compound to the 4,4 '-diamino-1, 1' -diphenylcyclohexane compound is 1.0-1.1:1, the pH value of the system is 8-8.5;
the molar ratio of the second compound to the 4,4 '-diamino-1, 1' -diphenylcyclohexane compound is 0.95-1.05:1, the pH value of the system is 9.5-10;
the molar ratio of the third compound to the 4,4 '-diamino-1, 1' -diphenylcyclohexane compound is 1.05 to 1.1:1, the pH value of the system is 8.5-9.5.
Wherein the post-treatment of the coupling product solution to obtain the acid orange disazo dye comprises the following steps:
heating the coupling product solution and adjusting the pH value to obtain an adjusted solution;
and sequentially salting out, filtering, drying, crushing and packaging the adjusting solution to obtain the acid orange disazo dye.
In a second aspect, the present invention provides an acid orange disazo dye having the structural formula:
the invention relates to a preparation method of acid orange disazo dye, which comprises the steps of diazotizing 4,4 '-diamino-1, 1' -diphenylcyclohexane compounds in the environment of sodium nitrite and hydrochloric acid to obtain diazonium salt of the 4,4 '-diamino-1, 1' -diphenylcyclohexane compounds; coupling the diazonium salt of the 4,4 '-diamino-1, 1' -diphenylcyclohexane compound twice and then esterifying to obtain a coupling product solution; and carrying out post-treatment on the coupling product solution to obtain the acid orange disazo dye. The acid orange disazo dye can be dyed under an acid condition, and has bright color, good lifting power, high solubility, good leveling property and high color fastness during dyeing. In addition, the acid orange disazo dye is safe and low in toxicity. Solves the problem of poor dyeing effect of the existing dye on the fabric.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the embodiments or the prior art will be briefly described below, it is obvious that the drawings in the following description are only some embodiments of the present invention, and for those skilled in the art, other drawings can be obtained according to the drawings without creative efforts.
FIG. 1 is a chemical equation for diazotizing 4,4 '-diamino-1, 1' -diphenylcyclohexane compounds in the presence of sodium nitrite and hydrochloric acid to obtain diazonium salts of 4,4 '-diamino-1, 1' -diphenylcyclohexane compounds.
FIG. 2 is a chemical equation for the procedure of twice coupling the diazonium salt of the 4,4 '-diamino-1, 1' -diphenylcyclohexane compound and then esterifying to obtain a coupled product solution.
FIG. 3 is a flow chart of a method for preparing acid orange disazo dye according to the present invention.
Detailed Description
Reference will now be made in detail to embodiments of the present invention, examples of which are illustrated in the accompanying drawings, wherein like or similar reference numerals refer to the same or similar elements or elements having the same or similar function throughout. The embodiments described below with reference to the drawings are illustrative and intended to be illustrative of the invention and are not to be construed as limiting the invention.
Referring to fig. 1 to 3, in a first aspect, the present invention provides a method for preparing acid orange disazo dye, comprising the following steps:
s1, diazotizing a 4,4 '-diamino-1, 1' -diphenylcyclohexane compound in the environment of sodium nitrite and hydrochloric acid to obtain a diazonium salt of the 4,4 '-diamino-1, 1' -diphenylcyclohexane compound;
specifically, the molar ratio of the 4,4 '-diamino-1, 1' -diphenylcyclohexane compound to the hydrochloric acid to the sodium nitrite is 1:4-6:2.0-2.05. Wherein, the sodium nitrite solution is added into the solution of the 4,4 '-diamino-1, 1' -diphenylcyclohexane compound and hydrochloric acid in the formula 1 quickly and slowly; preferably, the molar ratio of the 4,4 '-diamino-1, 1' -diphenylcyclohexane compound of the formula 1 to hydrochloric acid is 1:4 to 6, more preferably 1:5; preferably, the molar ratio of the 4,4 '-diamino-1, 1' -diphenylcyclohexane compound of the formula 1 to the sodium nitrite is 1:2.0 to 2.05, more preferably 1: 2.02-2.03.
The diazotization reaction is carried out at 0-5 ℃.
S2, carrying out coupling twice on the diazonium salt of the 4,4 '-diamino-1, 1' -diphenylcyclohexane compound, and then carrying out esterification to obtain a coupling product solution;
specifically, the diazonium salt of the 4,4 '-diamino-1, 1' -diphenylcyclohexane compound is coupled with a first compound at the temperature of 3-5 ℃ to obtain a primary coupling product; coupling the primary coupling product with a second compound at 5-8 ℃ to obtain a secondary coupling product; and (3) esterifying the secondary coupling product and a third compound at 68-75 ℃ to obtain a coupling product solution.
The molar ratio of the first compound to the 4,4 '-diamino-1, 1' -diphenylcyclohexane compound is 1.0 to 1.1:1, preferably 1.05 to 1.1:1; the pH value of the system is 8-8.5, and 8 is preferred; the molar ratio of the second compound to the 4,4 '-diamino-1, 1' -diphenylcyclohexane compound is 0.95-1.05:1, the pH value of the system is 9.5-10, and is preferably 9.5; the molar ratio of the third compound to the 4,4 '-diamino-1, 1' -diphenylcyclohexane compound is 1.05-1.1:1, the pH value of the system is 8.5-9.5, and is preferably 9.0.
The first compound is formula (3) in fig. 2, the second compound is formula (4) in fig. 2, and the third compound is formula (5) in fig. 2.
And S3, carrying out post-treatment on the coupling product solution to obtain the acid orange disazo dye.
Specifically, heating the coupling product solution and then adjusting the pH value to obtain an adjusted solution; and sequentially salting out, filtering, drying, crushing and packaging the adjusting solution to obtain the acid orange disazo dye.
Example 1:
step 1: diazotization of 4,4 '-diamino-1, 1' -diphenylcyclohexane
26.6g (0.1 mol) of 4,4 '-diamino-1, 1' -diphenylcyclohexane was weighed, 53ml (0.5 mol) of 30% hydrochloric acid and 300ml of water were added, and dissolved by stirring. Then adding ice to cool to 0 ℃, adding 30% aqueous solution prepared by 14g of sodium nitrite (0.203 mol) at first, quickly and slowly, reacting for 60 minutes, controlling the pH in the whole reaction process to be =1.0, obtaining 4,4 '-diamino-1, 1' -diphenylcyclohexane diazonium salt, detecting the test solution to be blue by a Congo red test paper, detecting the test solution to be blue by a starch potassium iodide test paper, eliminating excessive nitrous acid by sulfamic acid after the reaction is finished, and filtering to remove insoluble substances for later use.
And 2, step: coupling of
38.26g of sodium 2-naphthol-6, 8-disulfonate (0.11 mol) was added to 200ml of water, dissolved by adding 16g of soda ash and the pH was adjusted to 7.5. The solution of 4,4 '-diamino-1, 1' -diphenylcyclohexane diazo liquid is firstly added into the solution quickly and then slowly, and 10% sodium carbonate solution is used for controlling the reaction pH =8 and the temperature 5 ℃ for 5 hours, so as to generate the primary coupled monoazo reaction product. 9.4g of phenol (0.1 mol) were dissolved in 200ml of water. This solution was slowly added to the monoazo reaction product, and the reaction pH =9.5 and the temperature 8 ℃ were controlled with 10% soda solution for 3 hours, and the end point was detected by the ring penetration method. The sodium 1-naphthol-4 sulfonate is slightly excessive, and the 4,4' -diaminotriphenylmethane diazonium salt disappears to obtain a secondary coupling reaction product. The temperature of the secondary coupling compound is raised to 70 ℃, 21g (0.11 mol) of paratoluensulfonyl chloride is added into the secondary coupling compound for 1.5 hours, and the reaction is kept for 3 hours.
And step 3: post-treatment
Adding sodium chloride in an amount which is 10 percent of the total volume, salting out, filtering and drying to obtain 134g of finished dye. The color and light of the product are similar.
Application example:
the sample obtained in example 1 was used as acid orange disazo dye for dye application: 1g of chinlon, 1.0% of dyeing concentration, 1:50. transferring 20ml of dye solution into a dyeing cup, adding 1ml of acetic acid and 10ml of anhydrous sodium sulphate, adding distilled water to 50ml, and stirring uniformly. And putting the wetted fabric into a prepared dye bath at 40 ℃, heating to 95 ℃ for 45min, keeping the temperature at 95 ℃ for 45min, cooling to 60 ℃, taking out the dyed fabric, washing with water, and drying.
Finally, the application properties of the examples were measured, and the results are shown in Table 1.
TABLE 1
The color data (CIELAB) were determined and the results are shown in Table 2.
TABLE 2
The acid orange disazo dye can be used for dyeing under an acidic condition, and has the advantages of bright color, good lifting power, high solubility, good leveling property and high color fastness during dyeing. In addition, the acid orange disazo dye is safe and low in toxicity.
In a second aspect, the present invention provides an acid orange disazo dye having the structural formula:
in a third aspect, the present invention provides the use of an acid orange disazo dye for dyeing fabric, comprising: in an acid bath, the fabric is dyed with the acid orange disazo dye according to the invention.
Specifically, the fabric types include wool, silk, cotton, hemp, nylon, chinlon, terylene, and the like.
While the present invention has been described with reference to certain preferred embodiments and embodiments, it will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the invention as defined by the appended claims.
Claims (7)
1. The preparation method of the acid orange disazo dye is characterized by comprising the following steps:
diazotizing 4,4 '-diamino-1, 1' -diphenylcyclohexane compounds in the environment of sodium nitrite and hydrochloric acid to obtain diazonium salt of the 4,4 '-diamino-1, 1' -diphenylcyclohexane compounds;
coupling the diazonium salt of the 4,4 '-diamino-1, 1' -diphenylcyclohexane compound twice and then esterifying to obtain a coupling product solution;
and carrying out post-treatment on the coupling product solution to obtain the acid orange disazo dye.
2. The process for preparing acid orange disazo dye according to claim 1,
the molar ratio of the 4,4 '-diamino-1, 1' -diphenylcyclohexane compound to the hydrochloric acid to the sodium nitrite is 1:4-6:2.0-2.05.
3. The process for preparing acid orange disazo dye according to claim 2,
the diazotization reaction is carried out at 0-5 ℃.
4. The process for preparing acid orange disazo dye according to claim 3,
the method for preparing the coupling product solution comprises the following steps of performing coupling twice on the diazonium salt of the 4,4 '-diamino-1, 1' -diphenylcyclohexane compound, and then performing esterification to obtain the coupling product solution:
coupling the diazonium salt of the 4,4 '-diamino-1, 1' -diphenylcyclohexane compound with a first compound at 3-5 ℃ to obtain a primary coupling product;
coupling the primary coupling product with a second compound at 5-8 ℃ to obtain a secondary coupling product;
and (3) esterifying the secondary coupling product and a third compound at 68-75 ℃ to obtain a coupling product solution.
5. The process for preparing acid orange disazo dye according to claim 4,
the molar ratio of the first compound to the 4,4 '-diamino-1, 1' -diphenylcyclohexane compound is 1.0-1.1:1, the pH value of the system is 8-8.5;
the molar ratio of the second compound to the 4,4 '-diamino-1, 1' -diphenylcyclohexane compound is 0.95-1.05:1, the pH value of the system is 9.5-10;
the molar ratio of the third compound to the 4,4 '-diamino-1, 1' -diphenylcyclohexane compound is 1.05-1.1:1, the pH value of the system is 8.5-9.5.
6. The process for preparing acid orange disazo dye according to claim 5,
the post-treatment of the coupling product solution to obtain the acid orange disazo dye comprises the following steps:
heating the coupling product solution and adjusting the pH value to obtain an adjusted solution;
and sequentially salting out, filtering, drying, crushing and packaging the adjusting solution to obtain the acid orange disazo dye.
7. An acid orange disazo dye prepared by the method of claim 6, wherein the acid orange disazo dye has the following structural formula:
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| CN103415323A (en) * | 2011-03-10 | 2013-11-27 | 荷兰联合利华有限公司 | Composition |
| CN107997986A (en) * | 2017-12-08 | 2018-05-08 | 花安堂生物科技集团有限公司 | A kind of acidic hair coloring preparation and its hair colouring methods |
| FR3114502A1 (en) * | 2020-09-29 | 2022-04-01 | L'oreal | Process for removing make-up from colored keratin materials using an aqueous composition containing a water-soluble salt of a monovalent or divalent cation. |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD102398A1 (en) * | 1973-03-29 | 1973-12-12 | ||
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