CN113755027B - Reactive yellow dye composition, yellow dye and preparation method and application thereof - Google Patents
Reactive yellow dye composition, yellow dye and preparation method and application thereof Download PDFInfo
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- CN113755027B CN113755027B CN202111113132.1A CN202111113132A CN113755027B CN 113755027 B CN113755027 B CN 113755027B CN 202111113132 A CN202111113132 A CN 202111113132A CN 113755027 B CN113755027 B CN 113755027B
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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
- 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
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
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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
- 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
- C09B67/006—Preparation of organic pigments
- C09B67/0065—Preparation of organic pigments of organic pigments with only non-macromolecular compounds
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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
- 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
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- 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
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- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
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Abstract
The invention discloses a reactive yellow dye composition, a yellow dye and a preparation method and application thereof, and relates to the field of fine chemical industry, wherein the yellow reactive dye composition comprises a component A consisting of one or more compounds in a compound shown in a formula (I), and a component B consisting of one or more compounds in a compound shown in a formula (II); 50-100 parts by weight of component A and 0-50 parts by weight of component B, and the preparation method of the yellow dye comprises the following steps: and J acid acylation, coupling with a raw material containing R1 and R2, and finally hydrolyzing to obtain the reactive yellow dye. The dye does not generate three wastes during production and use, meets the current strict environmental protection requirements, and has good compatibility, high fixation rate and excellent comprehensive performance of various color fastness application performances in reactive dye dyeing application;
Description
Technical Field
The invention relates to the field of fine chemical industry, in particular to a reactive yellow dye composition, yellow dye prepared by the reactive yellow dye composition, a preparation method process and application of the prepared yellow reactive dye in dyeing and printing fibers or textiles thereof.
Background
With the increasing level of living, the requirements of people on textile products are also increasing, so that the requirements of reactive dyes for textile dyeing on various properties are becoming more severe. The reactive dye not only has excellent dyeing fastness and dyeing property, but also meets the environmental protection requirement. As a variety with larger market share, the reactive yellow dye is required to have good washing fastness and dyeing reproducibility, and higher lifting force and fixation rate. In order to improve the dyeing performance of the dye and enable the dye to have good dyeing effect, a plurality of reactive yellow dye patents appear in the industry.
Disclosure of Invention
In order to overcome the defects of poor dyeing fastness, poor dyeing performance and the like of yellow dyes in the prior art, a yellow dye composition and a yellow dye prepared by using the composition are provided. The dye composition has good lifting property, high fixation rate and excellent color fastness performances such as washing resistance, friction resistance, perspiration resistance and the like, is suitable for dyeing and printing of fibers or textile materials thereof, and is an environment-friendly reactive dye.
A first object of the present invention is to provide a reactive yellow dye composition comprising 50 to 100 parts by weight of component A and 0 to 50 parts by weight of component B.
The component A is at least one dye monomer A compound shown in the following formula (I):
wherein R is 1 And R is 2 Respectively H and SO 3 M 2 、-OCH 3 and-CH 3 One of (a), M 2 Is one of hydrogen, potassium, sodium, lithium and ammonium; r is R 3 is-SO 2 CH＝CH 2 or-SO 2 C 2 H 4 OSO 3 M 3 ，M 3 Is one of hydrogen, potassium, sodium, lithium and ammonium;
the component A is preferably selected from one of the following formulas or a mixture of two or more of the following formulas in any proportion:
wherein the dye monomers of formula (I) can each independently preferably be present in the form of a powder, a synthetic solution or an aqueous solution thereof.
The component B is at least one dye monomer B compound shown in the following formula (II);
wherein R is 4 Is H, -SO 3 M 2 、-OCH 3 and-CH 3 One of (a), M 2 Is one of hydrogen, potassium, sodium, lithium and ammonium; r is R 5 is-SO 2 CH＝CH 2 or-SO 2 C 2 H 4 OSO 3 M 4 ，M 4 Is one of hydrogen, potassium, sodium, lithium and ammonium.
The component B is preferably 0 to 40 parts by weight, and is preferably one of the following formulae or a mixture of two or more of them in any proportion:
preferably, the preparation method of the component A comprises the following steps:
step S1: adding ice water into a glass cup, then adding J acid and maleic anhydride, and carrying out an acylation reaction under the conditions that the temperature is 10-20 ℃ and the pH=3.0-6.5 to obtain a compound slurry of a formula (2), wherein the molecular structural formula of the formula (2) is as follows:
step S2: adding ice water into a glass cup, adding the formula (3) and sodium nitrite, then adding hydrochloric acid, and carrying out diazonium reaction at the temperature of 0 ℃ to obtain diazonium salt of the formula (4), wherein the molecular structural formulas of the formula (2) and the formula (3) are as follows:
step S3: adding the formula (2) into the synthesized diazonium salt formula (4), and carrying out coupling reaction under the conditions of an acid binding agent, the temperature of 0-10 ℃ and the pH=6.5-8.5 to obtain a compound slurry of the formula (5), wherein the structural formula of the compound of the formula (5) is as follows:
step S4: adding an alkaline compound into the formula (5), heating to 60-80 ℃, and carrying out hydrolysis reaction under the condition of pH=9-10 to obtain a dye finished product of the formula (I).
Preferably, the preparation method of the component A comprises the following steps:
step S1: adding 100-200 parts by mass of ice water into a glass cup, then adding 10-30 parts by mass of J acid and 5-20 parts by mass of maleic anhydride, and carrying out an acylation reaction for 2-5 hours at the temperature of 10-20 ℃ and under the condition of pH=3.0-6.5 to obtain a compound slurry of the formula (2), wherein the molecular structural formula of the formula (2) is as follows:
step S2: adding 100-200 parts by mass of ice water into a glass cup, then adding 20-40 parts by mass of formula (3), adding 7-10 parts by mass of sodium nitrite, then adding 50-70 parts by mass of hydrochloric acid, and carrying out diazonium reaction for 23 hours at the temperature of 0 ℃ to obtain diazonium salt of formula (4), wherein the molecular structural formulas of formula (2) and formula (3) are as follows:
step S3: adding the formula (2) into the synthesized diazonium salt formula (4), and carrying out coupling reaction for 3-7 hours under the conditions of an acid binding agent, the temperature of 0-10 ℃ and the pH=6.5-8.5 to obtain a compound slurry of the formula (5), wherein the compound of the formula (5) has the structural formula:
step S4: adding an alkaline compound into the formula (5), heating to 60-80 ℃, and carrying out hydrolysis reaction for 3-6 hours under the condition of pH=9-10 to obtain a dye finished product of the formula (I). In the step S3, the acid-binding agent is preferably sodium bicarbonate, sodium carbonate, a mixed solution of Na CO and CH COONa, or an inorganic ammonium salt. In the step S4, the alkaline compound is preferably a liquid alkali.
Preferably, the preparation method of the component B is that J acid and maleic anhydride are subjected to one-time acylation reaction at the temperature of 10-20 ℃ and the pH value of 3.0-6.5. The acylation reaction is carried out for 2-5 hours.
A second object of the present invention is to provide a yellow dye which, in addition to comprising any of the above reactive yellow dye compositions, incorporates adjuvants commonly used in the art, selected from one or more of dispersants, fillers and other performance improving adjuvants. The auxiliary agent is preferably a filler. The dispersant may preferably be one of a self-dispersant MF and a dispersant NNO. The filler may preferably be one or more selected from anhydrous sodium sulphate, methyl naphthalene sulphonic acid formaldehyde condensate, sodium hexametaphosphate, naphthalene sulphonic acid formaldehyde condensate. The other performance improving auxiliary may preferably be one or more selected from a dust-proof agent, a solubility improving agent, an alkali-resistant auxiliary, a surfactant, an accelerating agent. The auxiliaries are preferably present in the form of powders and/or solutions. The addition amount of the auxiliary agent is preferably 10-50% of the total weight of the product
The third object of the present invention is to provide a preparation method of yellow dye, which is prepared by mixing 50-100 parts by weight of the active yellow dye composition and 0-50 parts by weight of auxiliary agent. Specifically, the component A is prepared by mixing 50-100 parts by weight, the component B is prepared by mixing 0-50 parts by weight and the auxiliary agent is prepared by mixing 0-50 parts by weight, and the content of the component A is preferably 50-90%. The mixing mode adopts a mode of mixing liquid slurry and then spray drying or mixing monomer powder. The liquid slurry is mixed for at least 2 hours; the powder is mixed together, the lower opening material is fed back to the upper opening material for at least 2 times, and the total mixing time is at least 2 hours.
A fourth object of the present invention is to provide a use of a yellow reactive dye composition as a yellow reactive dye. Preferably applied to the printing of fibers or textiles thereof, optionally including dyeing or printing. Further, the yellow reactive dye composition is preferably used for dyeing and printing cellulose fibers, protein fibers, polyamide fibers or textiles or blended fabrics thereof. Optionally, the cellulose fibers include cotton fibers, hemp fibers and regenerated fibers; optionally, the protein fibers include wool, silk and wool fabrics; optionally, the yellow reactive dye is used for dyeing cotton fiber or regenerated fiber.
The above preferred conditions can be arbitrarily combined on the basis of not deviating from the common knowledge in the art, and thus, the embodiments of the present invention can be obtained.
Compared with the prior art, the invention has the positive progress effects that: the invention provides a dye composition, and the dye is prepared by using the composition, so that the prepared dye has excellent dyeing fastness and dyeing property, is very suitable for dyeing and printing cellulose materials, and has excellent lifting property, excellent color fastness and deep and rich color.
Detailed Description
Example 1:
the preparation of the compound of formula (1) is carried out by the following synthesis method
(1) Adding 100-200 parts by mass of ice water into a glass cup, then adding 10-30 parts by mass of J acid and 5-20 parts by mass of maleic anhydride, and carrying out an acylation reaction for 25 hours at the temperature of 10 ℃ and under the condition of pH=3.0.6.5 to obtain a compound slurry of the formula (2), wherein the molecular structural formula of the formula (2) is as follows:
(2) Adding 100-200 parts by mass of ice water into a glass cup, then adding 20-40 parts by mass of formula (3), adding 7-10 parts by mass of sodium nitrite, then adding 50-70 parts by mass of hydrochloric acid, and carrying out diazonium reaction for 23 hours at the temperature of 0 ℃ to obtain diazonium salt of formula (4), wherein the molecular structural formulas of the formula (3) and the formula (4) are as follows:
(3) Adding the formula (2) into the synthesized diazonium salt formula (4), and carrying out coupling reaction for 3-7 hours under the conditions of an acid binding agent, the temperature of 0-10 ℃ and the pH=6.5-8.5 to obtain a compound slurry of the formula (5), wherein the compound of the formula (5) has the structural formula:
(4) Adding an alkaline compound into the formula (5), heating to 60-80 ℃, and carrying out hydrolysis reaction for 3-6 hours under the condition of pH=9-10 to obtain a dye finished product of the formula (I) for standby.
Example 2:
(1) Adding 100-200 parts by mass of ice water into a glass cup, then adding 10-30 parts by mass of J acid and 5-20 parts by mass of maleic anhydride, and carrying out one-time acylation reaction for 25 hours at the temperature of 1020 ℃ and the pH value of 3.06.5 to obtain compound slurry.
(2) Adding 100-200 parts by mass of ice water into a glass cup, adding 20-40 parts by mass of para-ester, adding 7-10 parts by mass of sodium nitrite, adding 50-70 parts by mass of hydrochloric acid, and carrying out diazo reaction for 23 hours at the temperature of 0 ℃ to obtain para-ester diazonium salt for later use.
(3) And (3) adding J acid acylation into the synthesized para-ester diazonium salt, and carrying out coupling reaction for 3-7 hours at the temperature of 0-10 ℃ by using acid-binding agent sodium bicarbonate to adjust the pH value to be 6.5-8.5, so as to obtain coupling compound slurry.
(4) Adding an alkaline compound into the coupling compound, heating to 60-80 ℃, and carrying out hydrolysis reaction for 3-6 hours under the condition of pH=9-10 to obtain a dye finished product of the formula (1) for standby.
Example 3:
according to the data shown in Table 1, component A, component B, cosolvent and water are mixed by adopting liquid slurry, and then spray drying or powder mixing is carried out for 2 hours after the components are uniformly mixed.
Table 1: the dye raw material compositions of experiment numbers 1-7 were proportioned as follows:
dyeing property test
2g of the dye composition obtained according to experiment numbers 1-7 and 20ml/l of an anti-migration agent (sodium alginate paste 5%) were weighed and prepared into a solution of 20g/l with water; pouring the cotton woven cloth into a pad dyeing tank to carry out two-padding and two-padding (25 ℃ C., and the padding residual rate is 60-65%); prebaking (70 ℃); drying (150 ℃ x 2 min); pouring the prepared alkali liquor (200 g/l of anhydrous sodium sulfate, 20g/l of sodium carbonate, 5g/l of caustic soda and 1g/l of anti-dyeing salt S) into a pad dyeing tank, and putting the fabric into a fabric for two-padding and two-pad alkaline leaching (25 ℃ C., and the padding residual rate is 80%); steaming and fixing (102-105 ℃ for 45-90 s); then, after washing, soap boiling is carried out for 10min at 98 ℃ (2 g/l soap chips); finally, the resultant was washed with water, dried, and measured for color fastness, color light, etc., and the results are shown in Table 1.
TABLE 1
As can be seen from the above table, when the yellow reactive dye composition of the present invention is used as a yellow reactive dye, various performance indexes are good, especially the fastness to water, perspiration and rubbing are particularly good, the cut fixation rate is high, and the yellow reactive dye composition is an environment-friendly yellow reactive dye capable of meeting the requirements of high-end customers, and the above-mentioned is only a preferred embodiment of the present invention, and not intended to limit the present invention, any modification, equivalent replacement and change made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (10)
1. A reactive yellow dye composition characterized by: comprises 50-100 parts by weight of component A and 15-50 parts by weight of component B;
the component A comprises at least one of dye monomer A compounds shown in the following formula (I):
wherein R is 1 And R is 2 Respectively H and SO 3 M 2 、-OCH 3 and-CH 3 One of (a), M 2 Is one of hydrogen, potassium, sodium, lithium and ammonium; r is R 3 is-SO 2 CH＝CH 2 or-SO 2 C 2 H 4 OSO 3 M 3 ，M 3 Is one of hydrogen, potassium, sodium, lithium and ammonium;
the component B comprises at least one of dye monomer B compounds shown in the following formula (II);
wherein R is 4 Is H, -SO 3 M 2 、-OCH 3 and-CH 3 One of (a), M 2 Is one of hydrogen, potassium, sodium, lithium and ammonium; r is R 5 is-SO 2 CH＝CH 2 or-SO 2 C 2 H 4 OSO 3 M 4 ，M 4 Is one of hydrogen, potassium, sodium, lithium and ammonium.
2. A reactive yellow dye composition according to claim 1, wherein: the component A is selected from one of the following formulas or a mixture of two or more of the following formulas in any proportion:
3. a reactive yellow dye composition according to claim 1, wherein: the component B is 0-40 parts by weight and is selected from one or a mixture of more than two of the following formulas in any proportion:
4. a reactive yellow dye composition according to claim 1, wherein: the preparation method of the component A comprises the following steps:
step S1: adding ice water into a glass cup, then adding J acid and maleic anhydride, and carrying out an acylation reaction under the conditions that the temperature is 10-20 ℃ and the pH=3.0-6.5 to obtain a compound slurry of a formula (2), wherein the molecular structural formula of the formula (2) is as follows:
step S2: adding ice water into a glass cup, adding the formula (3) and sodium nitrite, then adding hydrochloric acid, and carrying out diazonium reaction at the temperature of 0-15 ℃ to obtain diazonium salt of the formula (4), wherein the molecular structural formulas of the formula (3) and the formula (4) are as follows:
step S3: adding the formula (2) into the synthesized diazonium salt formula (4), and carrying out coupling reaction under the conditions of an acid binding agent, the temperature of 0-10 ℃ and the pH=6.5-8.5 to obtain a compound slurry of the formula (5), wherein the structural formula of the compound of the formula (5) is as follows:
step S4: adding an alkaline compound into the formula (5), heating to 60-80 ℃, and carrying out hydrolysis reaction under the condition of pH=9-10 to obtain a dye finished product of the formula (I).
5. A reactive yellow dye composition according to claim 1, wherein: the preparation method of the component A is that J acid and maleic anhydride are subjected to one-time acylation reaction at the temperature of 10-20 ℃ and the pH value of 3.0-6.5.
6. A yellow dye, characterized by: the dye comprising the reactive yellow dye composition of any one of claims 1-5 and an auxiliary.
7. The method for preparing a yellow dye according to claim 6, wherein: the yellow dye is prepared by mixing 50-100 parts by weight of the active yellow dye composition and 0-50 parts by weight of the auxiliary agent.
8. The method for preparing a yellow dye according to claim 7, wherein: the mixing adopts a mode of mixing liquid slurry and then spray drying or mixing monomer powder.
9. Use of the reactive yellow dye composition according to any one of claims 1 to 5 as yellow dye.
10. Use according to claim 9, characterized in that the reactive yellow dye composition is used for the dyeing and printing of fibres or textiles thereof.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1333313A (en) * | 1970-12-12 | 1973-10-10 | Hoechst Ag | Water-soluble reactive metal complex monoazo dyestuffs and a process for their manufacture |
| US3873513A (en) * | 1968-08-06 | 1975-03-25 | Us Agriculture | Methylolated reaction product of a hydroxy carbamate and a cellulose-dyeing azo dyestuff containing a chlorotriozinyl group |
| CN111334086A (en) * | 2020-04-10 | 2020-06-26 | 浙江瑞华化工有限公司 | Maotai-red reactive dye composition and preparation method and application thereof |
| CN111607250A (en) * | 2020-06-15 | 2020-09-01 | 江苏德旺数码科技有限公司 | High-fastness reactive orange dye composition |
-
2021
- 2021-09-23 CN CN202111113132.1A patent/CN113755027B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3873513A (en) * | 1968-08-06 | 1975-03-25 | Us Agriculture | Methylolated reaction product of a hydroxy carbamate and a cellulose-dyeing azo dyestuff containing a chlorotriozinyl group |
| GB1333313A (en) * | 1970-12-12 | 1973-10-10 | Hoechst Ag | Water-soluble reactive metal complex monoazo dyestuffs and a process for their manufacture |
| CN111334086A (en) * | 2020-04-10 | 2020-06-26 | 浙江瑞华化工有限公司 | Maotai-red reactive dye composition and preparation method and application thereof |
| CN111607250A (en) * | 2020-06-15 | 2020-09-01 | 江苏德旺数码科技有限公司 | High-fastness reactive orange dye composition |
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