CN112341430A - Monoazo compound, preparation method and application thereof - Google Patents
Monoazo compound, preparation method and application thereof Download PDFInfo
- Publication number
- CN112341430A CN112341430A CN202011251616.8A CN202011251616A CN112341430A CN 112341430 A CN112341430 A CN 112341430A CN 202011251616 A CN202011251616 A CN 202011251616A CN 112341430 A CN112341430 A CN 112341430A
- Authority
- CN
- China
- Prior art keywords
- alkyl
- monoazo
- compound
- chain
- hydrogen
- 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.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
- C09B29/0059—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing only sulfur as heteroatom
-
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
- C09B29/0833—Amino benzenes characterised by the substituent on the benzene ring excepted the substituents: CH3, C2H5, O-alkyl, NHCO-alkyl, NHCOO-alkyl, NHCO- C6H5, NHCOO-C6H5
- C09B29/0834—Amino benzenes characterised by the substituent on the benzene ring excepted the substituents: CH3, C2H5, O-alkyl, NHCO-alkyl, NHCOO-alkyl, NHCO- C6H5, NHCOO-C6H5 linked through -O-
-
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
- C09B29/0833—Amino benzenes characterised by the substituent on the benzene ring excepted the substituents: CH3, C2H5, O-alkyl, NHCO-alkyl, NHCOO-alkyl, NHCO- C6H5, NHCOO-C6H5
- C09B29/0836—Amino benzenes characterised by the substituent on the benzene ring excepted the substituents: CH3, C2H5, O-alkyl, NHCO-alkyl, NHCOO-alkyl, NHCO- C6H5, NHCOO-C6H5 linked through -N=
- C09B29/0838—Amino benzenes characterised by the substituent on the benzene ring excepted the substituents: CH3, C2H5, O-alkyl, NHCO-alkyl, NHCOO-alkyl, NHCO- C6H5, NHCOO-C6H5 linked through -N= specific alkyl-CO-N-, aralkyl CON-, cycloalkyl CON-, alkyl OCON-
-
- 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
- D06P1/16—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 dispersed, e.g. acetate, dyestuffs
- D06P1/18—Azo 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
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/24—Polyamides; Polyurethanes
- D06P3/26—Polyamides; Polyurethanes using dispersed dyestuffs
-
- 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
- D06P3/34—Material containing ester groups
- D06P3/52—Polyesters
- D06P3/54—Polyesters using dispersed dyestuffs
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Dispersion Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
Abstract
The invention relates to a thiophene derivative as a diazo component monoazo compound, a preparation method and application thereof. The monoazo compound is shown as a formula (1), wherein R1Is hydrogen, methoxy, ethoxy, propoxy, butoxy, 2-methoxyethyl, halogen; r2，R3Means hydrogen, C1‑6A linear or branched alkyl or cycloalkyl chain, with or without intervening atoms in the alkyl chain, allyl, cyanoethyl, benzyl,Benzyl ethyl, alpha-methylbenzyl, -R6COOR7Wherein R is6Is methylene group, ethylene group, propylene group,
R7is C1‑6A linear or branched chain or a cycloalkane chain, with or without intervening atoms for the alkyl chain; r4Is hydrogen, methyl, ethyl, hydroxy, -NHO2S‑C1‑4Alkyl or substituted alkyl, -NHOC-C1‑4Alkyl or substituted alkyl, halogen, -NHO2S‑C1‑4Alkyl or substituted alkyl and-NHOC-C1‑4C in alkyl or substituted alkyl1‑4Is methyl, ethyl, substituted alkyl is 2-methoxyethyl, chloroethyl; r5Is C1‑4An alkyl group. The preparation method comprises the steps of preparing diazonium salt from a diazonium component in sulfuric acid, and coupling the diazonium salt with a coupling component in acid water to prepare the target compound. The dye obtained by the invention has high color development intensity, bright color and good application performance.
Description
Technical Field
The invention relates to the technical field of disperse dyes, in particular to a monoazo compound taking thiophene derivatives as a diazo component, and a preparation method and application thereof.
Background
With the development of textile industry, more and more functional new materials and new designs are applied to the production of textile garments and fabrics, such as the development of functional polyester fabrics, the application of polyester spandex stretch fabrics and novel polyester fiber fabrics, and the design of color collision matching of garments and fabrics, especially the growth of sports fabrics and outdoor fabrics, and these garments and fabrics have higher requirements on the washing fastness of disperse dyes. Although the conventional disperse dyes can dye, the molecular attraction between the dyes and fibers is greatly reduced, so that the fastness of the dyed fabric is reduced to different degrees, and particularly the washing fastness is reduced remarkably. Therefore, the development of new high water-washable dyes is a problem with great practical significance.
Disclosure of Invention
In order to solve the problems, the invention provides a monoazo compound using heterocyclic amino as a diazo component, and a preparation method and application thereof. The invention is particularly applicable to: the dyeing is carried out on terylene and spandex textile fabrics and terylene superfine fibers to obtain the effect with good light fastness, washing fastness and sublimation fastness.
The invention relates to a monoazo compound with a molecular structure of diazo component of thiophene derivatives as shown in formula (1),
(1) in the formula
R1Wherein is hydrogen, methoxy, ethoxy, propoxy, butoxy, 2-methoxyethyl, or halogen;
R2means hydrogen, C1-6Straight or branched alkyl or cycloalkyl chain, including, for the alkyl chain, interrupted or not interrupted, allyl, cyanoethyl, benzyl, phenethyl, phenylcarbonylmethoxy, -R6COOR7Wherein R is6Refers to methylene, ethylene or propylene groups; r7Is C1-6Straight or branched or cyclic alkyl chains, including with or without intervening atoms for the alkyl chain;
R3is hydrogen, allyl, cyanoethyl, benzyl, phenethyl, phenylcarbonylmethoxy, C1-6Straight, branched or cyclic alkyl chains, for alkyl chains, from C2Upwards, with or without the insertion of oxygen, nitrogen or sulphur atoms, and with or without the inclusion of atoms, -R, in the case of alkyl chains6COOR7Wherein R is6Is a methylene group, an ethylene group or a propylene group; r7Is C1-6Straight or branched or cyclic alkyl chains, including with or without intervening atoms for the alkyl chain;
R4refers to hydrogen, methyl, ethyl, hydroxy, -NHO2S-C1-4Alkyl or substituted alkyl, -NHOC-C1-4Alkyl or substituted alkyl, halogen, -NHO ═ S-C1-4Alkyl or substituted alkyl and-NHOC-C1-4C in alkyl or substituted alkyl1-4Is methyl, ethyl, substituted alkylThe radical is 2-methoxyethyl or chloroethyl;
R5is referred to as C1-4An alkyl group.
The monoazo compounds, optimized R, according to the invention1Refers to hydrogen, methoxy, ethoxy or 2-methoxyethyl.
The monoazo compounds, optimized R, according to the invention2Refers to ethyl, cyanoethyl, benzyl, -R6COOR7Wherein R is6Is a methylene group, an ethylene group, a propylene group, R7Is C1-6Straight or branched chain or cycloalkane chain, with or without inclusion of atoms in the alkyl chain.
The monoazo compounds, optimized R, according to the invention6Refers to methyl, ethyl or methyl methylene.
The monoazo compounds, optimized R, according to the invention7Refers to methyl or ethyl.
The monoazo compounds, optimized R, according to the invention4Refers to hydrogen, methyl, hydroxy, -NHO2S-C1-4Alkyl or-NHOC-C1-4An alkyl group.
The preparation method of the monoazo compound of the present invention comprises the steps of mixing the compound of formula (2)
Dissolving in acid, cooling to-5-20 ℃, dropwise adding nitrosyl sulfuric acid, keeping the temperature at-5-20 ℃ for 1-5 hours after adding nitrosyl sulfuric acid, and diazotizing to obtain diazonium salt for later use; dispersing the compound shown in the formula (3) in an acidic aqueous medium of sulfuric acid or acetic acid,
cooling to 0-15 ℃ for coupling reaction, dripping heavy nitrogen liquid while stirring, adding the heavy nitrogen liquid for 1-4 hours, preserving the heat for 2-6 hours at the same temperature, filtering and washing to obtain the product of the invention;
wherein R is1、R2、R3、R4And R5Has the definition of the formula (1) above;
wherein, the acid in the reaction is one or two mixed acids of sulfuric acid, formic acid, acetic acid, propionic acid and phosphoric acid;
wherein the diazotization temperature is-5-20 ℃;
wherein the coupling temperature is 0 ℃ to 15 ℃.
The preparation method of the monoazo compound has the optimized diazotization temperature of 0-10 ℃ in the reaction.
The preparation method of the monoazo compound has the coupling optimization temperature of 5-10 ℃ in the reaction.
In the preparation method of the monoazo compound, the acid in the reaction is one of concentrated sulfuric acid, acetic acid or phosphoric acid, or a mixture of any two of the concentrated sulfuric acid, the acetic acid and the phosphoric acid.
According to the preparation method of the monoazo compound, the diazotization temperature in the reaction is 5-10 ℃, the diazotization is not thorough at low temperature, the diazotization is unstable at high temperature, impurities are easily generated by decomposition, and the impurities are brought to the reaction at high or low temperature.
In the preparation method of the monoazo compound, the coupling temperature in the reaction is 5-10 ℃, the coupling temperature is low, the coupling time is long, and the diazo component is decomposed; the temperature is high, the coupling component is easy to hydrolyze, and impurities are generated, so that the purity of the dye is reduced.
The monoazo compound is used as disperse dye. The disperse dye is applied to dyeing or printing of polyester, polyamide fibers or fabrics thereof.
The disperse dye comprises a mixture of at least two monoazo dyes of formula (1) according to claim 1 of different structures.
The monoazo compound is characterized in that as shown in (1a),
the monoazo compound is characterized in that as shown in (1b),
the monoazo compound is characterized in that as shown in (1c),
the monoazo compound is characterized in that as shown in (1d),
the monoazo compound is characterized in that as shown in (1e),
the monoazo compound is characterized in that the monoazo compound is represented by (1f),
monoazo compounds according to claim 1 wherein (1g),
monoazo compounds according to claim 1 wherein (1h) represents
The monoazo compound and the mixture of monoazo compounds of the invention can be used as disperse dyes for hydrophobic fiber materials, especially for dyeing or printing and dyeing of polyester fibers, and polyamide textile dyeing requirements. Before the mixture of the monoazo compound and the monoazo compound with the novel structure is used, the mixture is mixed with a dispersing agent and a dispersing auxiliary agent and suspended in a liquid medium, and then sanding, microparticulation and drying are carried out to obtain the disperse dye shown in the formula (1); the dispersing auxiliary agent is one or more of an anionic dispersing agent and a nonionic auxiliary agent.
The anionic dispersant is one or more of a naphthalenesulfonic acid formaldehyde condensate, an alkyl naphthalenesulfonic acid formaldehyde condensate, a benzyl naphthalenesulfonic acid formaldehyde condensate and lignosulfonate; the nonionic auxiliary agent is fatty alcohol-polyoxyethylene ether or fatty acid-polyoxyethylene ester.
The mixture of the monoazo compound and the monoazo compound is added with an auxiliary agent, wherein the mixture of the monoazo compound and the monoazo compound accounts for 10-50% by weight, and the auxiliary agent accounts for 50-90% by weight.
The invention relates to a monoazo compound prepared by taking thiophene derivatives as diazo components, which is taken as disperse dye and has the following advantages compared with the traditional azo dye and anthraquinone dye which take aniline derivatives as diazo components:
(1) high color development strength and good color fastness. The dye of the invention is 3-4 times of the color development intensity of anthraquinone dyes with the same color. The sublimation fastness, washing fastness and lifting power of the dye are far higher than those of anthraquinone dyes.
(2) The diazo component is a heterocyclic compound, and the diazo component improves the structural molecular weight, so that the washing fastness of the disperse dye is improved, and the synthetic series of high-performance dyes have good practical significance and economic significance.
(3) Simple preparation process, low cost and less discharge of three wastes. In the process of preparing azo high-water-washing disperse dyes, the conventional aniline derivatives are used as azo disperse dyes of diazo components, and in order to achieve the purposes of high water washing and deep color, the desired effect can be achieved after diazotization, coupling, separation and drying and further cyanogen substitution reaction in an organic solvent. Long technological process and large amount of three wastes. The deep color high-water-washing disperse dye can achieve deep color and high-water-washing effects only by diazotization, coupling and separation without drying and cyanogen substitution reaction.
Meanwhile, the azo dye product can be in a single structure or a mixture of a plurality of dyes, and the composite dye can be a compound of a plurality of single dyes or can be directly synthesized into a mixed dye and then is commercially processed.
Detailed Description
In order to more clearly illustrate the technical solutions of the embodiments of the present invention, the present invention will be briefly described by the embodiments, and it is obvious that the embodiments described below are only examples of the present invention, and it is obvious for those skilled in the art that other technical solutions can be obtained according to the embodiments without creative efforts.
Example 1:
the starting materials used in the examples, formula (4) and formula (3a), can be prepared by known processes, and the other starting materials are commercially available commercial products suitable for dyes and intermediates.
120G sulfuric acid and 240G nitrosyl sulfuric acid were added to the flask, the temperature was lowered to 0-5 ℃ with stirring in an ice bath, and the 120G compound (4) was added for 1 hour, and after the addition was completed, the mixture was stirred at that temperature for 3 hours. After the reaction is finished, the diazonium salt is dropped into a mixture of 50ML sulfuric acid, 800G ice water and 160G compound (3a) at 0-5 ℃ within 1 hour, the mixture is continuously stirred for 3 hours, filtered and washed with water to be neutral to obtain the dye with the following formula,
the dye is used for dyeing polyester to obtain brilliant red light blue. λ max (nm) ═ 594nm
Example 2:
120G sulfuric acid and 240G nitrosyl sulfuric acid were added to the flask, the temperature was lowered to 0-5 ℃ with stirring in an ice bath, and the 120G compound (4) was added for 1 hour, and after the addition was completed, the mixture was stirred at that temperature for 3 hours. After completion of the reaction, the diazonium salt is dropped into a mixture of 50ML sulfuric acid, 800G ice water and 182G of the compound (3b) at 0 to 5 ℃ over 1 hour,
stirring for 3 hours, filtering, washing with water to be neutral to obtain the dye with the following formula,
the dye is used for dyeing polyester to obtain brilliant red light blue. λ max (nm) ═ 580nm
Example 3:
120G sulfuric acid and 240G nitrosyl sulfuric acid were added to the flask, the temperature was lowered to 0-5 ℃ with stirring in an ice bath, and the 120G compound (4) was added for 1 hour, and after the addition was completed, the mixture was stirred at that temperature for 3 hours. After completion of the reaction, the diazonium salt is dropped into a mixture of 50ML sulfuric acid, 800G ice water and 198G of the compound (3c) at 0 to 5 ℃ over 1 hour,
stirring for 3 hours, filtering, washing with water to be neutral to obtain the dye with the following formula,
the dye is used for dyeing polyester to obtain brilliant red light blue. λ max (nm) ═ 585nm
Example 4:
120G sulfuric acid and 240G nitrosyl sulfuric acid were added to the flask, the temperature was lowered to 0-5 ℃ with stirring in an ice bath, and the 120G compound (4) was added for 1 hour, and after the addition was completed, the mixture was stirred at that temperature for 3 hours. After completion of the reaction, the diazonium salt is dropped into a mixture of 50ML sulfuric acid, 800G ice water and 215G of the compound (3d) at 0 to 5 ℃ over 1 hour,
stirring for 3 hours, filtering, washing with water to be neutral to obtain the dye with the following formula,
the dye is used for dyeing polyester to obtain brilliant red light blue. λ max (nm) ═ 596nm
Example 5:
120G sulfuric acid and 240G nitrosyl sulfuric acid were added to the flask, the temperature was lowered to 0-5 ℃ with stirring in an ice bath, and the 120G compound (4) was added for 1 hour, and after the addition was completed, the mixture was stirred at that temperature for 3 hours. After completion of the reaction, the diazonium salt was dropped into a mixture of 50ML sulfuric acid, 800G ice water and 196G of the compound (3e) at 0 to 5 ℃ over 1 hour,
stirring for 3 hours, filtering, washing with water to be neutral to obtain the dye with the following formula,
the dye is used for dyeing polyester to obtain brilliant red light blue. λ max (nm) ═ 583nm
Example 6:
120G sulfuric acid and 240G nitrosyl sulfuric acid were added to the flask, the temperature was lowered to 0-5 ℃ with stirring in an ice bath, and the 120G compound (4) was added for 1 hour, and after the addition was completed, the mixture was stirred at that temperature for 3 hours. After completion of the reaction, the diazonium salt was dropped into a mixture of 50ML sulfuric acid, 800G ice water and 172.6G of the compound (3f) at 0 to 5 ℃ over 1 hour,
stirring for 3 hours, filtering, washing with water to be neutral to obtain the dye with the following formula,
the dye is used for dyeing polyester to obtain brilliant red light blue. λ max (nm) 551nm
Example 7:
120G sulfuric acid and 240G nitrosyl sulfuric acid were added to the flask, the temperature was lowered to 0-5 ℃ with stirring in an ice bath, and the 120G compound (4) was added for 1 hour, and after the addition was completed, the mixture was stirred at that temperature for 3 hours. After completion of the reaction, the diazonium salt was dropped into a mixture of 50ML sulfuric acid, 800G ice water and 170.2G of the compound (3G) at 0 to 5 ℃ over 1 hour,
stirring for 3 hours, filtering, washing with water to be neutral to obtain the dye with the following formula,
the dye is used for dyeing polyester to obtain brilliant red light blue. λ max (nm) ═ 600nm
Example 8:
120G sulfuric acid and 240G nitrosyl sulfuric acid were added to the flask, the temperature was lowered to 0-5 ℃ with stirring in an ice bath, and the 120G compound (4) was added for 1 hour, and after the addition was completed, the mixture was stirred at that temperature for 3 hours. After completion of the reaction, the diazonium salt was dropped into a mixture of 50ML sulfuric acid, 800G ice water and 215G of the compound (3j) at 0 to 5 ℃ over 1 hour,
stirring for 3 hours, filtering, washing with water to be neutral to obtain the dye with the following formula,
the dye is used for dyeing polyester to obtain brilliant red light blue. λ max (nm) ═ 584nm
Example 9:
a structure represented by the formula (2)
Diazotisation with nitrosulphuric acid in sulphuric acid medium, coupling the diazonium salt obtained with a compound of formula (3) in acidic medium
Wherein R is1、R2、R3、R4And R5Having the above definition of formula (1), the monoazo compound of the present invention represented by formula (1) is obtained.
The invention also relates to mixtures of at least two coupling compounds of different structure of the formula (1), which mixtures have better application properties. The mixtures according to the invention can be prepared by simply mixing the individual monoazo compounds in proportions, for example by mixing the monoazo compounds of the formulae (1a) and (1 c). Or at least two coupling components shown in the formula (3) can be mixed according to a certain proportion, and the mixture is coupled with the diazonium salt prepared by the structure shown in the formula (2) under an acidic condition to synthesize the mixed dye. The amount of the individual monoazo compounds or coupling components in the mixture can vary within wide limits, for example the weight of the individual azo compounds in the mixture according to the invention comprising the two monoazo compounds can be 95: 5 to 5: 95 parts, in particular 80: 20 to 20: 80 parts of the raw materials.
Examples 10 to 273 (Table one)
The dyes described below are likewise suitable for dyeing polyester fiber materials. They are prepared analogously to the examples:
watch 1
Application example:
and (3) measuring the solid content of the dye filter cake obtained according to the embodiment, calculating the dry content, adding a dispersing agent MF (shown in the table 2) and a proper amount of water, performing sand grinding dispersion in a sand mill, filtering out dye dispersion slurry when the sample is qualified through inspection, and performing quick drying to obtain corresponding dye commodity powder.
TABLE 2
| Dye material | Amount of crude dye on drying (gram) | Dispersant MF (gram) |
| Example 1 | 3.25 | 9 |
| Example 2 | 3 | 9 |
| Example 3 | 3.12 | 9 |
| Example 4 | 3.47 | 9 |
| Example 5 | 2.54 | 9 |
| Example 6 | 2.38 | 9 |
| Example 7 | 2.34 | 9 |
| Example 8 | 2.36 | 9 |
| Example 1+ example 3 | 1.63+1.56 | 9 |
| Example 2+ example 6 | 0.638+2.552 | 9 |
| Example 4+ example 5 | 0.3+2.453 | 9 |
Taking 0.1 g of each disperse dye finished product, placing the disperse dyes finished product in 100ml of water for uniform dispersion, transferring 25ml of a transfer pipette, placing the transfer pipette in a dye vat of a high-temperature high-pressure dyeing machine, adding 74ml of water, adjusting the pH value of a dye bath to be 5 by using a sodium acetate buffer solution, adding 5g of superfine polyester fiber standard cloth, closing the dye vat, and starting dyeing: heating from 60 ℃ to 130 ℃ within 45 minutes, keeping the temperature at 130 ℃ for dyeing for 60 minutes, stopping heat preservation, cooling to below 90 ℃, taking out the dyed sample, carrying out cold water washing and reduction washing, and drying. The color fastness to washing, light, rubbing and sublimation are respectively measured by using national standards GB/T3921-1997, GB/T8427-1998 and GB/T3290-1997 GN/T5718-1997. The test results are shown in Table 3.
TABLE 3
As shown in the table, the thiophene derivative used as the diazo component monoazo compound can obtain good deep color, good sublimation fastness, good washing fastness and good light fastness no matter the thiophene derivative is a monomer dye or a mixture when the thiophene derivative is applied to dyeing of polyester blended yarns and polyester superfine fiber textiles.
Claims (10)
1. A monoazo compound represented by the formula (1)
(1) In the formula
R1Refers to hydrogen, methoxy, ethoxy, propoxy, butoxy, 2-methoxyethyl, or halogen;
R2means hydrogen, C1-6Straight or branched alkyl or cycloalkyl chains, including, for the alkyl chain, interrupted or not interrupted atoms,Allyl, cyanoethyl, benzyl, phenethyl, phenylcarbonylmethoxy, -R6COOR7Wherein R is6Refers to methylene, ethylene or propylene groups; r7Is C1-6Straight or branched or cyclic alkyl chains, including with or without intervening atoms for the alkyl chain;
R3is hydrogen, allyl, cyanoethyl, benzyl, phenethyl, phenylcarbonylmethoxy, C1-6Straight, branched or cyclic alkyl chains, for alkyl chains, from C3-6With or without intervening oxygen, nitrogen or sulfur atoms, and with or without intervening atoms, -R for alkyl chains6COOR7Wherein R is6Is a methylene group, an ethylene group or a propylene group; r7Is C1-6Straight or branched or cyclic alkyl chains, including with or without intervening atoms for the alkyl chain;
R4refers to hydrogen, methyl, ethyl, hydroxy, -NHO2S-C1-4Alkyl or substituted alkyl, -NHOC-C1-4Alkyl or substituted alkyl, halogen, -NHO2S-C1-4Alkyl or substituted alkyl and-NHOC-C1-4C in alkyl or substituted alkyl1-4Is methyl, ethyl, substituted alkyl is 2-methoxyethyl or chloroethyl;
R5is referred to as C1-4An alkyl group.
2. Monoazo compounds according to claim 1 wherein R is1Is hydrogen, methoxy, ethoxy or 2-methoxyethyl.
3. Monoazo compounds according to claim 1 wherein R is2Is ethyl, cyanoethyl, benzyl, -R6COOR7Wherein R is6Is a methylene group, an ethylene group, a propylene group, R7Is C1-6Straight or branched chain or cycloalkane chain, with or without inclusion of atoms in the alkyl chain.
4. As claimed in claim 3The monoazo compound is characterized in that R is6Refers to methyl, ethyl or methyl methylene.
5. Monoazo compounds according to claim 1 or 3 wherein R is7Refers to methyl or ethyl.
6. Monoazo compounds according to claim 1 wherein R is4Refers to hydrogen, methyl, hydroxy, -NHO2S-C1-4Alkyl or-NHOC-C1-4An alkyl group.
7. A monoazo compound according to claim 1 wherein the monoazo compound is prepared by a process comprising the step of reacting a compound of formula (2)
Dissolving in acid, cooling to-5-20 ℃, dropwise adding nitrosyl sulfuric acid, keeping the temperature at-5-20 ℃ for 1-5 hours after adding nitrosyl sulfuric acid, and diazotizing to obtain diazonium salt for later use; dispersing the compound shown in the formula (3) in an acidic aqueous medium of sulfuric acid or acetic acid,
cooling to 0-15 ℃, then carrying out coupling reaction, dripping heavy nitrogen liquid while stirring, adding the heavy nitrogen liquid for 1-4 hours, preserving the heat for 2-6 hours at the same temperature, filtering, and washing with water to obtain the product of the invention;
wherein R is1、R2、R3、R4And R5Has the definition of the formula (1) above;
wherein, the acid in the reaction is one or two mixed acids of sulfuric acid, formic acid, acetic acid, propionic acid and phosphoric acid;
wherein the diazotization temperature is-5-20 ℃;
wherein the coupling temperature is 0 ℃ to 15 ℃.
8. Monoazo compounds according to claim 7, characterized in that: the temperature of diazotization in the reaction is 0-10 ℃.
9. Monoazo compounds according to claim 7, characterized in that: the temperature of coupling in the reaction is 5 ℃ to 10 ℃.
10. The monoazo compound according to claim 1, wherein: use as disperse dyes; the disperse dye is applied to the dyeing or printing of polyester, polyamide fiber or fabrics thereof; the disperse dye comprises a mixture of at least two monoazo dyes of formula (1) according to claim 1 of different structures.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202011251616.8A CN112341430A (en) | 2020-11-11 | 2020-11-11 | Monoazo compound, preparation method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202011251616.8A CN112341430A (en) | 2020-11-11 | 2020-11-11 | Monoazo compound, preparation method and application thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN112341430A true CN112341430A (en) | 2021-02-09 |
Family
ID=74363338
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202011251616.8A Pending CN112341430A (en) | 2020-11-11 | 2020-11-11 | Monoazo compound, preparation method and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN112341430A (en) |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1394365A (en) * | 1972-01-28 | 1975-05-14 | Impperial Chemical Ind Ltd | Disperse azo dyestuffs |
| US4257942A (en) * | 1977-10-06 | 1981-03-24 | Aziende Colori Nazionali Affini Acna S.P.A. | New water-insoluble azo dyes |
| US4507407A (en) * | 1984-06-25 | 1985-03-26 | Milliken Research Corporation | Process for in situ coloration of thermosetting resins |
| WO1996011987A1 (en) * | 1994-10-18 | 1996-04-25 | Basf Aktiengesellschaft | Methine and azo dye-containing dye mixtures |
| JPH0940659A (en) * | 1995-08-01 | 1997-02-10 | Mitsui Toatsu Chem Inc | Optical recording medium |
-
2020
- 2020-11-11 CN CN202011251616.8A patent/CN112341430A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1394365A (en) * | 1972-01-28 | 1975-05-14 | Impperial Chemical Ind Ltd | Disperse azo dyestuffs |
| US4257942A (en) * | 1977-10-06 | 1981-03-24 | Aziende Colori Nazionali Affini Acna S.P.A. | New water-insoluble azo dyes |
| US4507407A (en) * | 1984-06-25 | 1985-03-26 | Milliken Research Corporation | Process for in situ coloration of thermosetting resins |
| WO1996011987A1 (en) * | 1994-10-18 | 1996-04-25 | Basf Aktiengesellschaft | Methine and azo dye-containing dye mixtures |
| JPH0940659A (en) * | 1995-08-01 | 1997-02-10 | Mitsui Toatsu Chem Inc | Optical recording medium |
Non-Patent Citations (4)
| Title |
|---|
| ARNOLD T. PETERS和ADAM GBADAMOSI: "Disperse Dyes : 4-Hetarylazo Derivatives from N-P-Cyanoethyl-N-P-Hydroxyethylaniline", 《J. CHEM. TECH. BIOTECHNOL》 * |
| GEOFFREY HALLAS AND ANDREW D. TOWNS: "A Comparison of the Properties of Some 2-Aminothiophene- derived Disperse Dyes", 《DYES AND PIGMENT》 * |
| REGISTRY: "STN检索", 《STN检索》 * |
| 颜明贤等: "含羟基杂环系噻吩染料之合成及其性质之研究", 《J.CHIN COLLOLD ＆ INTERFACE SOC》 * |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5922034B2 (en) | Disperse azo dye | |
| CN102816453B (en) | Disperse dye monomeric compound and disperse dye | |
| CN1049674C (en) | Monoazo type pyridone series compound dye | |
| CN114316628A (en) | High-lifting-force monoazo disperse dye, and preparation and application methods thereof | |
| CN112646388A (en) | Pyrazole monoazo dye and preparation method thereof | |
| CN103709787B (en) | A kind of synthetic method of Azo type disperse dye composition | |
| CN110229541B (en) | Combined azo disperse dye and preparation method thereof | |
| CN112341430A (en) | Monoazo compound, preparation method and application thereof | |
| CN104592782B (en) | Be suitable to the azo type disperse dyes of dyeing in acid-alkaline bath, prepare and apply | |
| CN112341836B (en) | Weak acid red bisazo dye and preparation method thereof | |
| CN112442283B (en) | Azo type disperse dye compound suitable for dyeing in acid-alkaline bath, preparation method, composition and application thereof | |
| CN105238094B (en) | A kind of feux rouges blueness azo dispersion dyes with intensity of colour occurred frequently and preparation method thereof | |
| CN115386242B (en) | Preparation and application of flexible chain-connected disazo orange high-water-washing disperse dye compound | |
| KR102137478B1 (en) | Brilliant blue azo dye and method of preparation thereof, and its use | |
| CN115386243B (en) | Preparation and application of disazo red high-washing disperse dye compound connected by flexible chains | |
| CN109054429B (en) | Azo dye compound containing acetamide group and preparation method and application thereof | |
| CN111500088B (en) | Disperse yellow dye composition, dye product and application | |
| CN111484752A (en) | Dye compound, dye composition, and preparation method and application thereof | |
| US4642339A (en) | Thiazoleazophenylaminoethyl carbonyloxy-C8 -C10 -alkyl compounds useful as dyes for polyester fibers | |
| EP2859051B1 (en) | Anthraquinone azo dyes | |
| US4187218A (en) | Water-soluble acid azo dye | |
| CN117326972A (en) | Compound, preparation method thereof and application thereof in dye | |
| CN113462190B (en) | Azo dye compound with high washing fastness, preparation method and application | |
| CN110564177B (en) | Purple disperse dye composition for printing | |
| CN108864732B (en) | Azo dye compound containing methanesulfonamide group and preparation method and application thereof |
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 |