CN115521636A - Dicyan-containing sun-proof anthraquinone disperse dye and preparation method thereof - Google Patents
Dicyan-containing sun-proof anthraquinone disperse dye and preparation method thereof Download PDFInfo
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- CN115521636A CN115521636A CN202211302845.7A CN202211302845A CN115521636A CN 115521636 A CN115521636 A CN 115521636A CN 202211302845 A CN202211302845 A CN 202211302845A CN 115521636 A CN115521636 A CN 115521636A
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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
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/24—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being only condensed with an anthraquinone nucleus in 1-2 or 2-3 position
- C09B5/2409—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being only condensed with an anthraquinone nucleus in 1-2 or 2-3 position not provided for in one of the sub groups C09B5/26 - C09B5/62
- C09B5/2436—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being only condensed with an anthraquinone nucleus in 1-2 or 2-3 position not provided for in one of the sub groups C09B5/26 - C09B5/62 only nitrogen-containing hetero rings
- C09B5/2445—Phtaloyl isoindoles
- C09B5/2454—5,6 phtaloyl dihydro isoindoles
- C09B5/2463—1,3 oxo or imino derivatives
- C09B5/2472—1,3 dioxo derivatives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/58—[b]- or [c]-condensed
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Abstract
The invention belongs to the field of chemical industry, and particularly relates to a dicyan-containing sun-proof anthraquinone disperse dye and a preparation method thereof. The structural general formula of the dicyan-containing sun-proof anthraquinone-containing disperse dye is as follows:
Description
Technical Field
The invention belongs to the field of chemical industry, and particularly relates to a dicyano-containing sun-proof anthraquinone disperse dye and a preparation method thereof.
Technical Field
The disperse dyes can be divided into azo dyes and anthraquinone dyes according to chemical structures, wherein the anthraquinone disperse dyes are dyes with the largest dosage except the azo dyes and have the characteristics of bright and stable color, light resistance, good fastness and the like. However, with the more and more extensive application of the dyes in the modern printing and dyeing industry, the requirement of people on the light fastness of the dyes is continuously improved, and the traditional anthraquinone type disperse dyes are difficult to meet the light fastness requirement of the dyes under some special environments.
The process of photobleaching of anthraquinone disperse dyes is a very complicated process, and can be divided into photooxidation bleaching and photoreduction bleaching according to mechanisms. Both fading mechanisms are closely related to the molecular structure of the dye, and the light fastness of the dye is related to factors such as the chromogen structure of the dye, ultraviolet irradiation and the like. It is generally believed that the higher the density of the electron cloud in the amino group in the anthraquinone structure, the more readily it is oxidized to hydroxylamine, resulting in a decrease in light fastness. Therefore, the conventional method is to introduce an electron-withdrawing group to the ortho-position of the amino group of the anthraquinone type disperse dye to reduce the electron cloud density of the amino group, thereby improving the light fastness of the dye.
201610046791.0, an invention, 1, 4-diamino-2, 3-dicyan anthraquinone, provides a dye with cyano group directly introduced to ortho-position of anthraquinone amino group, but the chromatic light of the dye is shifted due to strong electric absorbability of cyano group, the dye is not pure blue dye, and the dyeing performance is poor.
201010142513.8, namely a preparation method of a disperse blue 60 and homologues thereof, provides an anthraquinone disperse dye C.I. disperse blue 60 with good light fastness (7 grade), and can meet the application requirements of most conventional textiles on light fastness. However, c.i. disperse blue 60 still fails to meet the light fastness requirements of textiles in special environments.
202111316457X, the invention, "light-fast anthraquinone disperse dyes and their preparation methods", provides two light-fast anthraquinone disperse dyes, the molecular structure of which contains hindered amine light-stable segments, with excellent light-fast fastness. However, the color fastness to washing is poor, and the requirement of the color fastness to washing of partial textiles cannot be met.
Disclosure of Invention
The invention aims to provide a light-fast anthraquinone disperse dye and a preparation method thereof, and the disperse dye has the characteristics of higher dye uptake, color fastness to washing and light fastness.
In order to solve the technical problems, the invention provides a dicyan-containing sun-proof anthraquinone disperse dye, which has a molecular structure general formula as follows:
in the formula: r is-CH 2 -CH 2 -or
As a further improvement of the sun-proof anthraquinone disperse dye, the disperse dye has a structural formula of any one of the following:
the invention also provides a preparation method of the sun-proof anthraquinone disperse dye, which comprises the following steps:
1) Dissolving the N, N-dicyanoethyl derivative and 1, 4-diaminoanthraquinone-2, 3-dicarboxylic anhydride in DMF, heating to 105-110 ℃, stirring and reacting for 3-5 hours to obtain a target disperse dye solution;
the molar ratio of the N, N-dicyanoethyl derivative to 1, 4-diaminoanthraquinone-2, 3-dicarboxylic anhydride is 3;
2) And carrying out post-treatment on the target disperse dye solution obtained in the step 1) to obtain the sun-proof anthraquinone disperse dye.
The method specifically comprises the following steps:
adding ethanol into the target disperse dye solution obtained in the step 1) for segregation, cooling to 25 +/-5 ℃, then carrying out suction filtration, washing a filter cake with ethanol, then washing with hot water (about 60-70 ℃), and drying (at 80 ℃ to constant weight) to obtain a finished product, namely the sun-proof anthraquinone disperse dye.
The reaction formula of the invention is as follows:
r is-CH 2 -CH 2 -or
When the N, N-dicyanoethyl derivative is N, N-dicyanoethyl-1, 2-ethylenediamine, the product obtained is
When the N, N-dicyanoethyl derivative is N, N-dicyanoethyl-1, 4-phenylenediamine, the resulting product is
The preparation method of the light-fast anthraquinone disperse dye adopts 1, 4-diaminoanthraquinone-2, 3-dicarboxylic anhydride and N, N-dicyanoethyl derivative as raw materials, introduces cyano groups on the basis of 1, 4-diaminoanthraquinone color bodies, and effectively improves the color fastness to washing and light fastness of the dye.
The sun-proof anthraquinone disperse dye is used for dyeing hydrophobic Polyester (PET) fibers, and the dyeing process refers to 202111316457X invention of the sun-proof anthraquinone disperse dye and a preparation method thereof.
The lightfast anthraquinone disperse dye is improved on the basis of a1, 4-diaminoanthraquinone chromophore structure, introduces a cyano group (namely N, N-dicyanoethyl-1, 2-ethylenediamine or N, N-dicyanoethyl-1, 4-phenylenediamine group), and utilizes the function of the cyano group to effectively absorb ultraviolet rays to inhibit the photobleaching reaction of the anthraquinone dye, thereby improving the lightfast fastness of the dye. The dye has wide application prospect in the field with strict requirement on light fastness.
It is to be emphasized that: the invention is a disperse dye containing cyan, and 201610046791.0, 201010142513.8 and 202111316457X provide a conventional disperse dye structure.
In conclusion, the light-fast anthraquinone disperse dye overcomes the defect that the traditional commercial anthraquinone disperse dye is not suitable for special environments with high requirements on light fastness, and meanwhile, as a novel anthraquinone disperse dye structure, the light-fast anthraquinone disperse dye has excellent light fastness and enriches the varieties of the high-light-fastness disperse dye.
Detailed Description
The invention will be further described with reference to specific examples, but the scope of the invention is not limited thereto:
1, 4-diamino-2, 3-dicarboxylic anhydride anthraquinone (CAS: 3176-87-2), N-dicyanoethyl-1, 2-ethanediamine (CAS: 55534-79-7), N-dicyanoethyl-1, 4-benzenediamine (CAS: 104851-97-0) are all known compounds.
Example 1, a light fast anthraquinone disperse dye containing dicyano and a preparation method thereof, comprising the following steps:
0.03mol (about 5.0 g) of N, N-dicyanoethyl-1, 2-ethylenediamine and 0.02mol (about 7.7 g) of 1, 4-diaminoanthraquinone-2, 3-dicarboxylic anhydride are added into a three-neck flask to be completely dissolved in DMF (40 mL), the mixture is heated and stirred at 105 ℃ for reaction for 5 hours until the reaction end point, then a proper amount (about 30 mL) of ethanol is added for segregation, the mixture is filtered after being cooled to the normal temperature (25 +/-5 ℃), a filter cake is washed by ethanol (about 30 mL), and then the filter cake is washed by hot water (about 100 mL) at 60 ℃, dried in an oven at 80 ℃ to constant weight, 8.34g (0.0182 mol) of the dried finished product is 94.5% in purity, and the yield is 91.4%, thus obtaining the target product A1.
1 H NMR(400MHz,DMSO-d6)：δ8.29(t,2H),7.85(d,2H),4.82(s,4H),3.59(t,2H),3.01(t,4H),2.73(t,4H),2.60(t,2H)；ESI MS(m/z,％):457.2([M+H] + ,100)。
Examples 2,
Adding 0.03mol (about 6.5 g) of N, N-dicyanoethyl-1, 4-phenylenediamine and 0.02mol (about 7.7 g) of 1, 4-diamino-2, 3-dicarboxylic anhydride anthraquinone into a three-neck flask, completely dissolving the N, N-dicyanoethyl-1, 4-phenylenediamine in DMF (40 mL), heating and reacting at 105 ℃ for 5 hours until the reaction end point, adding a proper amount of ethanol (about 30 mL) for segregation, cooling to normal temperature, carrying out suction filtration, washing a filter cake with ethanol, then washing with hot water, drying in an oven at 80 ℃ to constant weight, obtaining a finished product after drying, wherein the finished product is 8.94g (0.0177 mol), the purity is 96.4%, the yield is 92.3%, and the light-fast anthraquinone disperse dye A2 is obtained and has the following structure:
1 H NMR(400MHz,DMSO-d6)：δ8.31(t,2H),7.83(d,2H),7.09(d,2H),6.90(d,2H),4.80(s,4H),3.72(t,4H),3.14(t,4H)；ESI MS(m/z,％):505.2([M+H] + ,100)。
experiment 1,
0.25g of the dye (A1/A2), 0.5g of dispersant NNO, 12g of zirconium beads (1 mm) and 20mL of water are taken to be sanded in a sand mill for 8 hours, after the sanding is finished, fine nylon cloth is used for filtering, and the collected dispersion liquid is subjected to constant volume to 500 by using deionized watermL (in a 500mL volumetric flask), preparing a dye color paste; transferring disperse dye color paste according to the chroma requirement of owf 2 percent, and mixing the disperse dye color paste according to the bath ratio of 1:50 adding deionized water, then transferring the solution into a dyeing cup, adding the PET fabric to be dyed, placing the dyeing cup in a high-temperature high-pressure dyeing instrument, and setting the dyeing program as follows: heating to 90 deg.C at a rate of 2 deg.C/min, heating to 130 deg.C at a rate of 1 deg.C/min, holding for 1 hr, cooling to room temperature at a rate of 2 deg.C/min, taking out the dyed cloth sample, respectively sucking 1mL of dyed solution before and after dyeing into 10mL volumetric flasks, metering to scale with acetone, and measuring with ultraviolet-visible spectrophotometer at the maximum absorption wavelength of the dye (lambda) max ) And (4) measuring the absorbance, and calculating the dye uptake by using the Lambert-beer law.
The dye-uptake of A1 was 98.6%, and that of A2 was 97.9%.
The dyed cloth sample is subjected to color fastness to artificial light according to the national standard sublimation fastness test for textiles (GB/T5718-1997), the color fastness to washing of the color fastness test for textiles (GB/T3921-2008) and the color fastness test for textiles: xenon arc (GB/T8427-2008) requires reduction cleaning (reduction cleaning process is 2g/L sodium hydrosulfite, 1g/L NaOH, bath ratio is 1:
the dye A1 and the dye A2 are used for dyeing cloth samples, the sublimation fastness is grade 5, the color fastness to washing is grade 5, and the light fastness is grade 8.
Comparative experiment 1,
The detection was carried out according to the method described in the above experiment 1, with the c.i. disperse blue 60 dye replacing the dye of the present invention: the dye uptake is 92.5%, the fastness to sublimation is 4-5 grade, and the fastness to light is 8 grade.
Specific property pairs are shown in table 1 below.
TABLE 1
| Dye material | Dye uptake/% | Colour fastness to sublimation | Color fastness to light |
| C.i. disperse blue 60 | 92.5 | 4-5 | 7 |
| A1 | 98.6 | 5 | 8 |
| A2 | 97.9 | 5 | 8 |
As can be seen from the results in table 1, the light fastness of A1 and A2 is superior to that of c.i. disperse blue 60 having the same color matrix structure, the sublimation fastness and the light fastness can be further improved by introducing cyano groups on the basis of the 1, 4-diaminoanthraquinone color body structure, and the dye uptake of A1 and A2 is higher than that of c.i. disperse blue 60, and the dye uptake is good.
Comparative example 1, the N, N-dicyanoethyl-1, 2-ethylenediamine in example 1 was changed to N, N-diethyl-1, 2-ethylenediamine, and the remainder was identical to example 1. The obtained product is:
the dye uptake was 89.7% as determined by the method described in experiment 1; the fastness to sublimation is grade 4, and the fastness to light is grade 6-7. The performance versus A1 ratio is shown in table 2 below.
Comparative example 2, the product A1 was changed to 1, 4-diamino-2, 3-dicyanoanthraquinone,
the dye uptake was 78.5% as determined by the method described in experiment 1 above; the fastness to sublimation is grade 4, and the fastness to light is grade 6-7. The performance versus A1 ratio is shown in table 2 below.
TABLE 2
| Dye material | Dye uptake/% | Color fastness to sublimation | Color fastness to light |
| A1 | 98.6 | 5 | 8 |
| Comparative example 1 | 89.7 | 4 | 6-7 |
| Comparative example 2 | 78.5 | 4 | 6-7 |
As can be seen from the results in Table 2, the light fastness of A1 is superior to that of comparative example 1 in which the color base structures are the same and comparative example 2 in which a cyano group is directly introduced in the ortho-position of the anthraquinone amino group, the sublimation fastness and the light fastness can be further improved by introducing the cyano group on the basis of the 1, 4-diaminoanthraquinone color body structure, and the dye uptake of A1 is higher than that of comparative examples 1 and 2, and the dye uptake of A1 is good.
Comparative example 3, N-dicyanoethyl-1, 2-ethylenediamine in example 1 was changed to tetramethylpiperidinamine, and the remainder was identical to example 1. The obtained product is:
the dye uptake was 95.8% as determined by the method described in experiment 1 above; the fastness to sublimation is grade 4, the fastness to washing is grade 3, and the fastness to sunlight is grade 8. The performance against A1 ratio is shown in table 3 below.
Comparative example 4, N-dicyanoethyl-1, 2-ethylenediamine in example 1 was changed to pentamethylpiperidine, and the remainder was identical to example 1. The obtained product is:
the dye uptake was 97.4% as determined by the method described in experiment 1 above; the fastness to sublimation is grade 4, the fastness to washing is grade 3, and the fastness to sunlight is grade 8. The performance versus A1 ratio is shown in table 3 below.
TABLE 3
| Dye material | Dye uptake/% | Color fastness to sublimation | Color fastness to washing | Color fastness to light |
| A1 | 98.6 | 5 | 5 | 8 |
| Comparative example 3 | 95.8 | 4 | 3 | 8 |
| Comparative example 4 | 97.4 | 4 | 3 | 8 |
As can be seen from the results in Table 3, the sublimation fastness and the washing fastness of A1 are superior to those of comparative example 3 and comparative example 4, in which the structures of the color precursors are the same, which shows that the sublimation fastness and the washing fastness can be further improved by introducing a cyano group based on the structure of the 1, 4-diaminoanthraquinone color body, and the dye uptake of A1 is higher than that of comparative examples 3 and 4, so that the dye uptake of A1 is good.
Finally, it is also noted that the above-mentioned list is only a few specific embodiments of the present invention. It is obvious that the invention is not limited to the above embodiments, but that many variations are possible. All modifications which can be derived or suggested by the person skilled in the art from the present disclosure are to be considered within the scope of the present invention.
Claims (5)
1. The light-fast anthraquinone disperse dye containing dicyan is characterized in that the general structural formula is as follows:
in the formula: r is-CH 2 -CH 2 -or
2. The dicyan-containing lightfast anthraquinone disperse dye according to claim 1, wherein the structural formula is any one of the following:
3. a process for preparing a dicyano containing lightfast anthraquinone-based disperse dye according to claim 1 or 2, which comprises the steps of:
1) Dissolving the N, N-dicyanoethyl derivative and 1, 4-diaminoanthraquinone-2, 3-dicarboxylic anhydride in DMF, heating to 105-110 ℃, stirring and reacting for 3-5 hours to obtain a target disperse dye solution;
the molar ratio of the N, N-dicyanoethyl derivative to 1, 4-diaminoanthraquinone-2, 3-dicarboxylic anhydride is 3;
2) And carrying out post-treatment on the target disperse dye solution obtained in the step 1) to obtain the sun-proof anthraquinone disperse dye.
4. The preparation method of the dicyan-containing lightfast anthraquinone-containing disperse dye according to claim 3, wherein the dicyan-containing disperse dye is prepared by the following steps:
the N, N-dicyanoethyl derivatives are N, N-dicyanoethyl-1, 2-ethylenediamine and N, N-dicyanoethyl-1, 4-phenylenediamine.
5. The method for preparing dicyan containing lightfast anthraquinone disperse dye according to claim 3 or 4, wherein the post-treatment of the step 2) is as follows:
adding ethanol into the target disperse dye solution obtained in the step 1) for segregation, cooling to 25 +/-5 ℃, carrying out suction filtration, washing a filter cake with ethanol, washing with hot water, and drying to obtain the sun-proof anthraquinone disperse dye.
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| CN102618084A (en) * | 2012-02-27 | 2012-08-01 | 中南林业科技大学 | Heterocyclic ring blue disperse dye and synthesizing method and application thereof |
| CN104893340A (en) * | 2015-04-16 | 2015-09-09 | 南通恒盛精细化工有限公司 | Novel technology for dispersing turquoise blue GL |
| CN113930085A (en) * | 2021-11-08 | 2022-01-14 | 浙江理工大学 | Sun-proof anthraquinone disperse dye and preparation method thereof |
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2022
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Patent Citations (7)
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| CN1218798A (en) * | 1992-07-08 | 1999-06-09 | Basf公司 | Process for preparing 1,4-diamino anthraquinone-2,3-dicyan |
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| CN101338081A (en) * | 2008-07-11 | 2009-01-07 | 浙江龙盛集团股份有限公司 | Disperse dark blue dye composition |
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