CN112457684A - Acid red dye for fur and preparation method and application thereof - Google Patents
Acid red dye for fur and preparation method and application thereof Download PDFInfo
- Publication number
- CN112457684A CN112457684A CN202011547422.2A CN202011547422A CN112457684A CN 112457684 A CN112457684 A CN 112457684A CN 202011547422 A CN202011547422 A CN 202011547422A CN 112457684 A CN112457684 A CN 112457684A
- Authority
- CN
- China
- Prior art keywords
- acid red
- fur
- formula
- red dye
- dye
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Images
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
- C09B57/00—Other synthetic dyes of known constitution
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/18—Ring systems of four or more rings
-
- 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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0072—Preparations with anionic dyes or reactive dyes
- C09B67/0073—Preparations of acid or reactive dyes in liquid form
-
- 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
- D06P1/39—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 acid dyes
- D06P1/40—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 acid dyes using acid dyes without azo groups
-
- 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
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/30—Material containing basic nitrogen containing amide groups furs feathers, dead hair, furskins, pelts
- D06P3/3008—Material containing basic nitrogen containing amide groups furs feathers, dead hair, furskins, pelts using acid dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Coloring (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
The invention relates to an acid red dye for fur, a preparation method and application thereof, wherein the chemical structure of the acid red dye for fur is shown as a formula (I), and the preparation method comprises the following steps: the acid red dye for fur shown in the formula (I) is obtained by reacting a compound shown in the formula (II) and a compound shown in the formula (III) serving as raw materials under the catalysis of a catalyst. The invention develops a brand-new acid red dye, which has good compatibility and level-dyeing property with other dyes such as acid blue and acid yellow, has excellent fastness indexes such as perspiration fastness, light fastness, dry and wet rubbing fastness and washing fastness, and is very suitable for dyeing fur. The preparation method of the acid red dye for fur is simple and easy to operate, is very suitable for large-scale industrial production, and has good practicability. The acid red dye for fur prepared by the method has high yield and high purity.
Description
Technical Field
The invention belongs to the technical field of dyes, particularly relates to an acid red dye and a preparation method and application thereof, and particularly relates to an acid red dye for fur and a preparation method and application thereof.
Background
Along with the popularization of fur overcoats in common people, people pay more and more attention to the color light and fastness of furs, and particularly, the red dye special for furs has high requirements on light fastness and dry and wet rubbing fastness, so that people in the fur field pay attention to the fur.
Although the acid red 88 has good compatibility and level-dyeing property, the light fastness can hardly meet the requirements of customers; most of red dyes with good fastness disclosed in the prior art, such as an acid red dye composition disclosed in CN101177545A, mainly comprises one or more components A with a structure shown in formula (I) and one or more components B with a structure shown in formula (II) or the acid red dye composition consists of one or more components A with a structure shown in formula (I) and one or more components B with a structure shown in formula (II), and red dyed fabrics with good performances such as heat sensitivity, stability, bright color, sun resistance, washing resistance, sweat resistance and the like can be obtained by adjusting the proportion of different components; for example, CN1058277C, which is a new non-carcinogenic monoazo acid red dye, contains no carcinogenic mutagenic aromatic amine, and has the same color fastness performance as that of forbidden acid red 35 dye, such as sunlight, soaping, sweat stain, tweed, sea water, etc. and thus can replace forbidden acid red 35 dye, and these dyes have poor compatibility and synchronism with acid blue and acid yellow.
Therefore, it is necessary to develop a blue-biased red dye, which can be matched with blue and yellow to produce bright dyes with good fastness.
Disclosure of Invention
Aiming at the defects of the prior art, the invention aims to provide an acid red dye and a preparation method and application thereof, and particularly provides the acid red dye for fur and the preparation method and application thereof.
In order to achieve the purpose, the invention adopts the following technical scheme:
in a first aspect, the present invention provides an acid red dye for fur (herein named acid red HFR), wherein the chemical structure of the acid red dye for fur is shown as formula (i):
the invention develops a brand-new acid red dye with the structure as shown in the specification, the dye has good compatibility with other dyes such as acid blue and acid yellow, has good level-dyeing property, has excellent fastness indexes such as perspiration fastness, light fastness, dry and wet rubbing fastness and washing fastness, and is very suitable for dyeing fur.
In a second aspect, the present invention provides a process for producing acid red dye for fur according to the first aspect, the process comprising the steps of:
reacting a compound (white solid) shown in a formula (II) and a compound (light gray solid) shown in a formula (III) serving as raw materials under the catalysis of a catalyst to obtain an acid red dye (red solid) for fur shown in a formula (I);
the preparation method of the acid red dye for fur (named acid red HFR in the invention) is simple and easy to operate, is very suitable for large-scale industrial production, and has good practicability. The acid red dye for fur prepared by the method has high yield and high purity.
Preferably, the preparation method comprises the following steps:
(1) mixing the compound shown in the formula (II) with water, heating and preserving heat;
(2) adding a compound shown as a formula (III) into the product obtained in the step (1), then adding a catalyst, adjusting the pH value, and reacting until the end point.
Preferably, the mass ratio of the compound represented by the formula (II) in the step (1) to water is 1 (50-300), such as 1:50, 1:80, 1:100, 1:150, 1:200, 1:230, 1:250 or 1:300, and other specific values in the numerical range can be selected, and are not described in detail herein, and preferably 1 (80-230).
The mass ratio of the compound shown in the formula (II) to water is specially selected to be 1 (50-300) because the purity and the yield are reduced if the amount of water is relatively reduced, mainly the water amount is not enough and is difficult to filter, and a filter cake is difficult to wash; if the amount of water used is relatively excessive, the product yield is seriously affected.
Preferably, the temperature in step (1) is raised to 60-80 ℃, for example, 60 ℃, 65 ℃, 68 ℃, 70 ℃, 72 ℃, 75 ℃ or 80 ℃, etc., preferably 68-72 ℃, and other specific values in the numerical range can be selected, which is not described herein again.
Preferably, the heat preservation time in the step (1) is 40-80min, for example, 40min, 50min, 60min, 70min or 80min, and other specific values in the numerical range can be selected, and are not repeated herein.
The heating and heat preservation treatment is to ensure that the compound shown in the formula (II) is fully pulped and has no obvious particles, so that the reaction is more complete, and the purity and yield of the reaction are improved.
Preferably, the compound represented by the formula (III) is added to the product of the step (1) in the step (2) for 25-35min, such as 25min, 28min, 30min, 32min or 35min, and the temperature is controlled at 60-80 ℃, such as 60 ℃, 65 ℃, 68 ℃, 70 ℃, 72 ℃, 75 ℃ or 80 ℃, and the like, preferably 68-72 ℃; other specific point values within the above numerical range can be selected, and are not described in detail herein.
The reason why the duration of adding the compound represented by the formula (III) to the product of the step (1) is 25 to 35min is that if the duration is further shortened, the dissolution effect of the compound represented by the formula (III) in the reaction system is affected, and the reaction effect is further affected.
Preferably, the mass ratio of the compound represented by the formula (III) to the compound represented by the formula (II) in the step (2) is (1.1-1.3):1, such as 1.1:1, 1.2:1 or 1.3:1, and other specific values in the numerical range can be selected, and are not repeated herein.
The mass ratio of the compound of the formula (III) to the compound of the formula (II) is specifically selected in the range of (1.1 to 1.3):1 because if the relative amount of the compound of the formula (III) is further reduced, the reaction of the compound of the formula (II) is incomplete, resulting in an excessively low yield; if the relative amount of the compound represented by the formula (III) is further increased, more by-products are produced and the purity is not high.
Preferably, the catalyst in step (2) comprises ferrous chloride, iron powder, cuprous chloride or cuprous sulfate, preferably cuprous sulfate.
When the catalyst is cuprous sulfate, the time required by the reaction is shortest, and the reaction time required by the ferrous chloride, the iron powder and the cuprous chloride is 8h, 10h and 7h respectively; meanwhile, the yield and the purity of the reaction are also highest.
Preferably, the mass of the catalyst in the step (2) is 1-7% of that of the compound shown in the formula (II), such as 1%, 2%, 3%, 4%, 5%, 6%, or 7%, and other specific values in the numerical range can be selected, and are not described in detail herein, and are preferably 3-5%.
The mass of the catalyst is 1-7% of that of the compound shown in the formula (II) because if the using amount of the catalyst is further reduced, the reaction time is prolonged to exceed 13h, and the time cost is consumed; if the amount of the catalyst is further increased, the formation of by-products is easily caused, and the purity of the dye is reduced.
Preferably, the pH value adjustment in the step (2) uses an alkaline solution.
Preferably, the alkaline solution comprises a sodium bicarbonate solution.
Preferably, the pH is adjusted to 7-8, for example, pH 7.0, pH 7.2, pH 7.5, pH 7.8, pH 8.0, etc., and other specific values in the value range can be selected, which is not described herein again.
The pH value is adjusted to 7-8 because the reaction time is prolonged due to further reduction of the pH value, and the purity and the yield are influenced; further increases in pH also affect purity and yield.
Preferably, the reaction in step (2) is carried out at 60-80 ℃, for example, 60 ℃, 65 ℃, 68 ℃, 70 ℃, 72 ℃, 75 ℃ or 80 ℃, etc., and other specific values in the numerical range can be selected, which are not described in detail herein, preferably 68-72 ℃.
The reaction temperature is specifically selected to be 60-80 ℃, when the reaction temperature is further reduced, the reaction process is slow, the reaction time is long, more byproducts are obtained, the purity is not high, and the yield is too low; when the reaction temperature is too high, the solubility of the acid red HFR is too good, and the solubility in water is too high, resulting in too low a yield.
Preferably, the end point of the reaction in step (2) is monitored by thin layer chromatography and the developing agent comprises cyclohexane.
Preferably, the reaction in step (2) is terminated, and then is incubated at 68-72 deg.C (e.g., 68 deg.C, 69 deg.C, 70 deg.C, 71 deg.C, 72 deg.C, etc.) for 40-60min (e.g., 40min, 45min, 50min, 55min, 60min, etc.), filtered, and washed with 8-12% (e.g., 8%, 9%, 10%, 11%, 12%, etc.) aqueous sodium chloride solution.
As a preferred technical scheme of the invention, the preparation method of the acid red dye for fur comprises the following steps:
(1) mixing a compound shown as a formula (II) with water according to a mass ratio of 1 (50-300), heating to 60-80 ℃, and preserving heat for 40-80 min;
(2) slowly adding the compound shown in the formula (III) into the product in the step (1) for 25-35min, controlling the temperature at 60-80 ℃, wherein the mass ratio of the compound shown in the formula (III) to the compound shown in the formula (II) is (1.1-1.3): 1;
(3) then adding a catalyst with the mass of 1-7% of the compound shown in the formula (II), adjusting the pH value to 7-8 by using 30% sodium bicarbonate solution, reacting at 60-80 ℃ until the end point, and monitoring by using a thin layer chromatography, wherein a developing agent comprises cyclohexane;
(4) and (3) after the reaction is finished, preserving the heat for 40-60min at 68-72 ℃, filtering, and washing with 8-12% sodium chloride aqueous solution to obtain the acid red dye for the fur.
In a third aspect, the present invention provides a use of the acid red dye for fur according to the first aspect for dyeing fur, wherein the dye used for dyeing fur is a single acid red dye for fur according to the first aspect or a complex dye comprising the acid red dye for fur according to the first aspect.
In practical application, those skilled in the art can use the acid red dye of the present invention in combination with other dyes such as acid blue 25 and acid yellow 49 according to actual needs, and the acid red dye has good compatibility. The acid red dye of the present invention is excellent in perspiration fastness, light fastness, dry and wet rubbing fastness and washing fastness, whether used alone or in combination.
Compared with the prior art, the invention has the following beneficial effects:
the invention develops a brand-new acid red dye (named acid red HFR in the invention), which has good compatibility with other dyes such as acid blue and acid yellow, good level-dyeing property and excellent fastness indexes such as perspiration fastness, light fastness, dry-wet rubbing fastness and washing fastness, and is very suitable for dyeing fur. The preparation method of the acid red dye for fur is simple and easy to operate, is very suitable for large-scale industrial production, and has good practicability. The acid red dye for fur prepared by the method has high yield and high purity.
Drawings
FIG. 1 is a high performance liquid chromatogram of the acid red dye for fur prepared in example 3;
FIG. 2 is a high performance liquid chromatogram of the acid red dye for fur prepared in example 4.
Detailed Description
To further illustrate the technical means and effects of the present invention, the following further describes the technical solution of the present invention with reference to the preferred embodiments of the present invention, but the present invention is not limited to the scope of the embodiments.
The compounds of formula (II) (HPLC ≥ 97%), the compounds of formula (III) (HPLC ≥ 99%), cuprous sulfate (HPLC ≥ 96%), ferrous chloride, iron powder, cuprous chloride, sodium bicarbonate (HPLC ≥ 98%), cyclohexane (analytically pure ≥ 99.99%) in the following examples were purchased from the alatin chemical reagent net.
The purity of the product calculated in the following example was determined by Shimadzu LC-10ATvp HPLC, wherein the mobile phase was: 65/35 flow rate, 1.0mL/min, and type of chromatography column Thermo ScientificTM DNAPacTMRP HPLC column.
The compounds of formula (I), formula (II) and formula (III) referred to in the following examples are as follows:
example 1
This example provides an acid red dye for fur having the following structure, and the preparation method thereof is as follows:
(1) mixing 4.5g of a compound shown as a formula (II) with water according to a mass ratio of 1:180, heating to 70 ℃, and keeping the temperature for 60 min;
(2) slowly adding the compound shown in the formula (III) into the product obtained in the step (1) for 30min, and controlling the temperature at 70 ℃, wherein the mass ratio of the compound shown in the formula (III) to the compound shown in the formula (II) is 1.2: 1;
(3) then cuprous sulfate with the mass of 3% of that of the compound shown in the formula (II) is added, the pH value is adjusted to 7.5 by using 30% sodium bicarbonate solution, the reaction is carried out at 70 ℃ until the end point, the monitoring is carried out by using thin layer chromatography, the developing agent is cyclohexane, and the reaction is completed within 5 hours;
(4) and (3) after the reaction is finished, preserving the temperature for 50min at 70 ℃, filtering, and washing by using 10% sodium chloride aqueous solution to obtain the acid red dye for fur. The product was tested for purity and yield as shown in table 1.
Example 2
This example provides an acid red dye for fur of the following constitution, which was prepared by a method different from that of example 1 only in that the temperature in step (1) was raised to 20 ℃, the temperature in step (2) was controlled to 20 ℃, the reaction temperature in step (3) was 20 ℃ and the temperature in step (4) was maintained at 20 ℃. All other conditions remained unchanged. The product was tested for purity and yield as shown in table 1.
Example 3
This example provides an acid red dye for fur of the following constitution, which was prepared by a method different from that of example 1 only in that the temperature in step (1) was raised to 40 ℃, the temperature in step (2) was controlled to 40 ℃, the reaction temperature in step (3) was 40 ℃ and the temperature in step (4) was maintained at 40 ℃. All other conditions remained unchanged. The product was tested for purity and yield as shown in table 1. Its high performance liquid chromatography is shown in figure 1.
Example 4
This example provides an acid red dye for fur of the following constitution, which was prepared by a method different from that of example 1 only in that the temperature in step (1) was raised to 60 ℃, the temperature in step (2) was controlled to 60 ℃, the reaction temperature in step (3) was 60 ℃ and the temperature in step (4) was maintained at 60 ℃. All other conditions remained unchanged. The product was tested for purity and yield as shown in table 1. Its high performance liquid chromatography is shown in FIG. 2.
Example 5
This example provides an acid red dye for fur of the following constitution, which was prepared by a method different from that of example 1 only in that the temperature in step (1) was raised to 80 ℃, the temperature in step (2) was controlled to 80 ℃, the reaction temperature in step (3) was 80 ℃ and the temperature in step (4) was maintained at 80 ℃. All other conditions remained unchanged. The product was tested for purity and yield as shown in table 1.
Example 6
This example provides an acid red dye for fur of the following constitution, which was prepared by a method different from example 1 only in that the temperature was raised to 90 ℃ in step (1), the temperature in step (2) was controlled to 90 ℃, the reaction temperature in step (3) was 90 ℃ and the temperature in step (4) was maintained at 90 ℃. All other conditions remained unchanged. The product was tested for purity and yield as shown in table 1.
Examples 7 to 11
This example provides an acid red dye for fur of the following structure, which was prepared by a method different from example 1 only in that the mass ratios of the compound represented by the formula (II) in the step (1) to water were 1:50, 1:80, 1:120, 1:230, and 1:300, respectively. All other conditions remained unchanged. The product was tested for purity and yield as shown in table 1.
Examples 12 to 14
This example provides an acid red dye for fur of the following structure, and the preparation method thereof is different from that of example 1 only in that the catalysts added in step (3) are ferrous chloride, iron powder, and cuprous chloride in this order. All other conditions remained unchanged. The product was tested for purity and yield as shown in table 1.
Examples 15 to 17
This example provides an acid red dye for fur of the following structure, which was prepared by a method different from example 1 only in that the amounts of the catalysts added in step (3) were 1%, 5%, and 7% in this order. All other conditions remained unchanged. The product was tested for purity and yield as shown in table 1.
Examples 18 to 21
This example provides an acid red dye for furs of the following structure, which is prepared by a process different from example 1 only in that the amount of the compound of the formula (II) is kept constant, but the mass ratios of the compound of the formula (III) to the compound of the formula (II) are 0.97:1, 1.05:1, 1.30:1, 1.40:1, respectively. All other conditions remained unchanged. The product was tested for purity and yield as shown in table 1.
Examples 22 to 24
This example provides an acid red dye for fur of the following structure, which is prepared by a method different from example 1 only in that the pH is adjusted to 3.5, 5.5, 9.5 in order by using a 30% sodium bicarbonate solution in step (3). All other conditions remained unchanged. The product was tested for purity and yield as shown in table 1.
Evaluation test:
(1) product purity and yield are shown in table 1:
TABLE 1
From the data in table 1, it can be seen that: the preparation method of the acid red dye for fur, which is provided by the invention, has the advantages of high purity and high yield, and the purity and the yield of the product can be obviously influenced by the reaction temperature, the amount of water, the type of the catalyst, the amount of the catalyst, the mass ratio of the two raw materials and the pH value of a reaction system.
(2) Evaluation of fastness index
Three dyes were prepared, one of which was the acid red HFR of the present invention prepared in example 1 alone; the second is a compound dye prepared by mixing the acid red HFR, the acid blue 25 and the acid yellow 49 according to the invention in a mass ratio of 5:7:8 in example 1; the third is a compound dye prepared by mixing the acid red HFR, the acid blue 25 and the acid yellow 49 according to the invention in a mass ratio of 10:1:1 in example 1. The staining was performed according to the following procedure:
(2.1) selecting skins: selecting raw leather with clean fur, wherein the shrinkage temperature is more than or equal to 95 ℃;
(2.2) dyeing at a bath ratio of 20:1 at a temperature of 70 ℃:
(2.2.1)0.8ml/L of fur leveling agent DL for 30 min;
(2.2.2) acid Red HFR 0.5ml/L for 60 min;
or silver gray (0.5ml/L acid red HFR, 0.7ml/L acid blue 25, 0.8ml/L acid yellow 49) for 60 min;
or wine red (1ml/L acid red HFR, 0.1ml/L acid blue 25, 0.1ml/L acid yellow 49) for 60 min;
(2.2.3)1.0 ml/L85% formic acid, 60 min;
(2.2.4)1.0 ml/L85% formic acid, 30 min;
(2.2.5) peeling, cleaning, spin-drying, drying and finishing.
Evaluating the obtained dyed leather by four indexes of perspiration fastness, light fastness, dry and wet rubbing fastness and washing fastness, wherein the light fastness adopts Japanese standard JIS L0842-2008, and the highest grade is 5; the washing fastness is referenced to GB/T3921-2008; the dry and wet rubbing fastness is in reference to GB/T3922; perspiration fastness is referred to ISO 105E04: 1996. The results are shown in table 2:
TABLE 2
Name of dye | Fastness to perspiration | Color fastness to sunlight | Dry and wet rubbing fastness | Fastness to washing |
Acid Red HFR | Grade 3-4 | Grade 5 | Grade 5 | Grade 5 |
Silver ash | 4 stage | 4-5 stages | Grade 5 | 4-5 stages |
Wine red | 4 stage | 4-5 stages | Grade 5 | 4-5 stages |
As can be seen from the data in Table 2: the acid red dye has good fastness indexes no matter used alone or in combination.
The applicant states that the present invention is illustrated by the above examples to show the acid red dye for furs and the preparation method and application thereof, but the present invention is not limited to the above examples, i.e. it does not mean that the present invention must be implemented by the above examples. It should be understood by those skilled in the art that any modification of the present invention, equivalent substitutions of the raw materials of the product of the present invention, addition of auxiliary components, selection of specific modes, etc., are within the scope and disclosure of the present invention.
The preferred embodiments of the present invention have been described in detail, however, the present invention is not limited to the specific details of the above embodiments, and various simple modifications may be made to the technical solution of the present invention within the technical idea of the present invention, and these simple modifications are within the protective scope of the present invention.
It should be noted that the various technical features described in the above embodiments can be combined in any suitable manner without contradiction, and the invention is not described in any way for the possible combinations in order to avoid unnecessary repetition.
Claims (10)
2. the process for producing acid red dye for fur according to claim 1, wherein the process comprises the steps of:
reacting a compound shown in a formula (II) and a compound shown in a formula (III) serving as raw materials under the catalysis of a catalyst to obtain an acid red dye for fur shown in a formula (I);
3. the process for producing acid red dye for fur according to claim 2, wherein the process comprises the steps of:
(1) mixing the compound shown in the formula (II) with water, heating and preserving heat;
(2) adding a compound shown as a formula (III) into the product obtained in the step (1), then adding a catalyst, adjusting the pH value, and reacting until the end point.
4. The process for producing acid red dyes for fur use according to claim 3, wherein the mass ratio of the compound represented by the formula (II) in the step (1) to water is 1 (50-300), preferably 1 (80-230);
preferably, the temperature of step (1) is raised to 60-80 ℃, preferably 68-72 ℃;
preferably, the heat preservation time of the step (1) is 40-80 min.
5. The process for the preparation of acid red dyes for skins as claimed in claim 3 or 4, wherein the compound of formula (III) is added to the product of step (1) in step (2) for a period of 25-35min at a temperature of 60-80 ℃, preferably 68-72 ℃;
preferably, the mass ratio of the compound represented by the formula (III) to the compound represented by the formula (II) in the step (2) is (1.1-1.3): 1.
6. The process for the preparation of acid red dyes for skins as claimed in any one of claims 3 to 5, wherein the catalyst of step (2) comprises ferrous chloride, iron powder, cuprous chloride or cuprous sulfate, preferably cuprous sulfate;
preferably, the mass of the catalyst in step (2) is 1 to 7%, preferably 3 to 5%, of the mass of the compound of formula (II).
7. The process for producing acid red dye for fur according to any of claims 3 to 6, wherein the pH adjustment in the step (2) is carried out using an alkaline solution;
preferably, the alkaline solution comprises a sodium bicarbonate solution;
preferably, the pH is adjusted to 7-8.
8. The process for producing acid red dyes for furs according to any of claims 3 to 7, wherein the reaction in the step (2) is carried out at 60 to 80 ℃, preferably 68 to 72 ℃;
preferably, the end point of the reaction in step (2) is monitored by thin layer chromatography and the developing agent comprises cyclohexane.
9. The process for producing acid red dyes for furs according to any of claims 3 to 8, wherein the reaction of the step (2) is terminated and then the temperature is maintained at 68 to 72 ℃ for 40 to 60 minutes, filtered and washed with 8 to 12% aqueous sodium chloride solution.
10. Use of the acid red dye for fur according to claim 1 for dyeing fur, wherein the dye used for dyeing fur is the single acid red dye for fur according to claim 1 or a combination dye comprising the acid red dye for fur according to claim 1.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202011547422.2A CN112457684B (en) | 2020-12-24 | 2020-12-24 | Acid red dye for fur and preparation method and application thereof |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202011547422.2A CN112457684B (en) | 2020-12-24 | 2020-12-24 | Acid red dye for fur and preparation method and application thereof |
Publications (2)
Publication Number | Publication Date |
---|---|
CN112457684A true CN112457684A (en) | 2021-03-09 |
CN112457684B CN112457684B (en) | 2022-12-06 |
Family
ID=74803873
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202011547422.2A Active CN112457684B (en) | 2020-12-24 | 2020-12-24 | Acid red dye for fur and preparation method and application thereof |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN112457684B (en) |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3376320A (en) * | 1958-04-23 | 1968-04-02 | Geigy Ag J R | Anthraquinone dyestuffs |
US3534038A (en) * | 1965-11-16 | 1970-10-13 | Bayer Ag | Anthrapyrimadone and anthrapyridone dyestuffs containing an n-methylenecarboxamide group |
JP2006124611A (en) * | 2004-11-01 | 2006-05-18 | Canon Inc | Coloring compound and ink composition |
CN102936427A (en) * | 2012-08-03 | 2013-02-20 | 上海色如丹染料化工有限公司 | Light-resistant red ink jet dye mixture |
-
2020
- 2020-12-24 CN CN202011547422.2A patent/CN112457684B/en active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3376320A (en) * | 1958-04-23 | 1968-04-02 | Geigy Ag J R | Anthraquinone dyestuffs |
US3534038A (en) * | 1965-11-16 | 1970-10-13 | Bayer Ag | Anthrapyrimadone and anthrapyridone dyestuffs containing an n-methylenecarboxamide group |
JP2006124611A (en) * | 2004-11-01 | 2006-05-18 | Canon Inc | Coloring compound and ink composition |
CN102936427A (en) * | 2012-08-03 | 2013-02-20 | 上海色如丹染料化工有限公司 | Light-resistant red ink jet dye mixture |
Non-Patent Citations (1)
Title |
---|
穆振义: "《乌尔曼反应在染料合成中的应用》", 《染料工业》 * |
Also Published As
Publication number | Publication date |
---|---|
CN112457684B (en) | 2022-12-06 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN102978980B (en) | Polyester cotton one bath process dye | |
CN102660146B (en) | Oxidation-resistant disperse dye composition and preparation and application thereof | |
CN106245352A (en) | A kind of polyester-cotton blend microcapsule dispersion reactive dye One Bath Dyeing Process | |
CN111995879B (en) | Method for enhancing alkali resistance and oxidation resistance of benzisothiazole disperse dye | |
CN107476081B (en) | Dyeing and finishing process of polyester fiber-cellulose fiber mixed textile | |
CN113292867B (en) | Environment-friendly reactive dye and preparation method thereof | |
CN102605652A (en) | Method for dyeing pure silk by regarding rare earth material as mordant | |
CN114315636B (en) | Synthesis method of 1-propyl- [4- (4' -butylphenylazo) ] azobenzene | |
CN112457684B (en) | Acid red dye for fur and preparation method and application thereof | |
CN106590012B (en) | The isomer mixture of CLT acid prepares the method and product of acid dyes original powder | |
Bardole et al. | Iron salts in the post-metallization of mordant dyes | |
CN105086498A (en) | Heterocycle alkaline-washable carboxylic acid ethyl ester type disperse dye and preparation method thereof | |
CN102888766B (en) | Processing method for removing hydrolyzed reactive dyes on cotton knitted fabric by using solvent water system | |
CN106590013B (en) | The isomer mixture of CLT acid prepares acid dyes original powder and product | |
CN104629401B (en) | Bisazo disperse dye and preparation method and application thereof | |
CN104693141A (en) | Disperse dye compound as well as preparation method and use of disperse dye compound | |
CN108586274B (en) | Precursor of blue anthraquinone reactive disperse dye and preparation method thereof | |
JPS5818472B2 (en) | Dyeing method for cellulose fibers | |
CN106084874B (en) | A kind of disperse dyes and preparation method and application | |
CN105481722B (en) | Preparation method of 1, 4-diamino-2, 3-dicyanoanthraquinone | |
CN110294718B (en) | Azo purple red dye matrix and preparation method and application thereof | |
CN102493218A (en) | Method for carrying out dyeing by structure-modified anthraquinone natural dye | |
WO2019223016A1 (en) | Blue anthraquinone active disperse dye and preparation method therefor | |
US4013636A (en) | N,n-diethyl-4-(2,4-dinitro-6-alkylsulfonylphenylazo)-2-alkoxy-5-alkyl-carbonylaminoanilines | |
JPS5818474B2 (en) | Dyeing method for cellulose fibers |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant |