CN116102898A - Preparation method of direct blending dark blue - Google Patents
Preparation method of direct blending dark blue Download PDFInfo
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- CN116102898A CN116102898A CN202310152053.4A CN202310152053A CN116102898A CN 116102898 A CN116102898 A CN 116102898A CN 202310152053 A CN202310152053 A CN 202310152053A CN 116102898 A CN116102898 A CN 116102898A
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- Prior art keywords
- reaction
- solution
- coupling
- diaminodiphenylamine
- diazotization
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Links
- 238000002156 mixing Methods 0.000 title claims abstract description 19
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 42
- 238000006243 chemical reaction Methods 0.000 claims abstract description 39
- 238000005859 coupling reaction Methods 0.000 claims abstract description 34
- 238000006193 diazotization reaction Methods 0.000 claims abstract description 29
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims abstract description 28
- 230000008878 coupling Effects 0.000 claims abstract description 21
- 238000010168 coupling process Methods 0.000 claims abstract description 21
- 239000002253 acid Substances 0.000 claims abstract description 18
- 239000000463 material Substances 0.000 claims abstract description 16
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims abstract description 14
- 235000010288 sodium nitrite Nutrition 0.000 claims abstract description 14
- 238000000034 method Methods 0.000 claims abstract description 7
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims abstract description 7
- 235000017557 sodium bicarbonate Nutrition 0.000 claims abstract description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000001035 drying Methods 0.000 claims abstract description 4
- 238000005185 salting out Methods 0.000 claims abstract description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 12
- 239000012954 diazonium Substances 0.000 claims description 12
- 230000001276 controlling effect Effects 0.000 claims description 9
- 150000001989 diazonium salts Chemical class 0.000 claims description 9
- 239000000047 product Substances 0.000 claims description 7
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 claims description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
- 230000002378 acidificating effect Effects 0.000 claims description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 6
- 238000003825 pressing Methods 0.000 claims description 6
- 230000001105 regulatory effect Effects 0.000 claims description 6
- 239000011780 sodium chloride Substances 0.000 claims description 6
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims description 3
- CAMXVZOXBADHNJ-UHFFFAOYSA-N ammonium nitrite Chemical compound [NH4+].[O-]N=O CAMXVZOXBADHNJ-UHFFFAOYSA-N 0.000 claims description 3
- 238000010009 beating Methods 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 239000012065 filter cake Substances 0.000 claims description 3
- 239000000706 filtrate Substances 0.000 claims description 3
- 238000000227 grinding Methods 0.000 claims description 3
- 238000006386 neutralization reaction Methods 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 3
- 239000010865 sewage Substances 0.000 claims description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- 238000006277 sulfonation reaction Methods 0.000 claims description 3
- 239000002351 wastewater Substances 0.000 claims description 3
- 238000004043 dyeing Methods 0.000 abstract description 9
- 239000000975 dye Substances 0.000 abstract description 5
- 238000007639 printing Methods 0.000 abstract description 5
- 230000009286 beneficial effect Effects 0.000 abstract description 2
- GBBJCSTXCAQSSJ-XQXXSGGOSA-N clevudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1[C@H](F)[C@@H](O)[C@H](CO)O1 GBBJCSTXCAQSSJ-XQXXSGGOSA-N 0.000 abstract 1
- 229960005338 clevudine Drugs 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 238000000746 purification Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000011161 development Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000009940 knitting Methods 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- VKURVCNKVWKGLX-UHFFFAOYSA-N 5-amino-2-(4-aminoanilino)benzenesulfonic acid Chemical compound C1=CC(N)=CC=C1NC1=CC=C(N)C=C1S(O)(=O)=O VKURVCNKVWKGLX-UHFFFAOYSA-N 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000000982 direct dye Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 229910052595 hematite Inorganic materials 0.000 description 1
- 239000011019 hematite Substances 0.000 description 1
- LIKBJVNGSGBSGK-UHFFFAOYSA-N iron(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Fe+3].[Fe+3] LIKBJVNGSGBSGK-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/50—Tetrazo dyes
- C09B35/56—Tetrazo dyes of the type
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/22—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof from sulfonic acids, by reactions not involving the formation of sulfo or halosulfonyl groups; from sulfonic halides by reactions not involving the formation of halosulfonyl groups
Abstract
The invention discloses a preparation method of direct blending dark blue, and belongs to the field of printing and dyeing. The method comprises the following steps: s1, diazotizing, namely putting 3000kg of water, 4000kg of ice, 1500kg of 4.4' -diaminodiphenylamine-2-sulfonic acid and 3140kg of 30% hydrochloric acid solution into a closed reaction tank, and adding 2500kg of prepared 30% sodium nitrite solution; s2, coupling once, and adding excessive sodium bicarbonate into the prepared 15% clevudine solution; s3, secondary diazotization, namely adding 30% hydrochloric acid solution and ice into the primary coupling material through a high-level tank, and adding 30% sodium nitrite solution; s4, secondary coupling, namely adding a pre-prepared clev acid solution into the materials after the secondary diazotization reaction through an overhead tank, and carrying out secondary coupling reaction; s5, salting out, press filtration and drying. The invention ensures that the direct blending dark blue light is less poor and yellowish green, is beneficial to the subsequent market sales, does not need to use other dyes for color mixing, and reduces the cost.
Description
Technical Field
The invention relates to the field of printing and dyeing, in particular to a preparation method of direct blending dark blue.
Background
Dyeing and finishing is also called dyeing and finishing, and is a processing mode, and is also a general term of pretreatment, dyeing, printing, finishing, washing water and the like; the dyeing and finishing profession of the family now incorporates the light engineering profession; as early as six and seven thousand years ago in the new stone age, our ancestors were able to dye linen red with hematite powder. The original clan living in the Qinghai-Tidamu basin Nomuhong area can dye the knitting wool into yellow, red, brown, blue and the like, and the dyed knitting wool with color stripes is continuously enriched in color along with the continuous improvement and development of dyeing technology. The development trend of the printing and dyeing industry is that the printing and dyeing machine is efficient, energy-saving and environment-friendly, and the three aspects complement each other and are indispensable. Productivity is required to develop, and improvement of production efficiency is the most direct means; the energy saving is up to the stage that measures must be taken; the energy-saving measures are adopted, the productivity is developed, and meanwhile, the environmental protection consciousness and the pollution treatment means are also needed.
The direct blending dark blue is one of important varieties of direct dyes, and is prepared by adopting 4.4' -diaminodiphenylamine-2-sulfonic acid as a raw material through diazotization, primary coupling, secondary diazotization, secondary coupling and purification processes.
The existing direct blending dark blue light is worse and is yellowish green, so that the market is not free, and other dyes are needed for color mixing during sales, so that the cost is increased.
Disclosure of Invention
For the existing problems, the invention aims to provide a direct blending dark blue preparation method for solving the problems in the background technology.
In order to achieve the above purpose, the present invention provides the following technical solutions:
a preparation method of direct blending dark blue comprises the following steps:
s1, diazotizing
3000kg of water, 4000kg of ice, 1500kg of 4.4 '-diaminodiphenylamine-2-sulfonic acid and 3140kg of 30% hydrochloric acid solution are put into a closed reaction tank, the hydrochloric acid solution and the 4.4' -diaminodiphenylamine-2-sulfonic acid are added into a sulfonation kettle through a metering tank, beating and grinding are carried out for 0.5h at the temperature of about 0 ℃ in the kettle, 2500kg of prepared 30% sodium nitrite solution is added under the liquid level, and diazonium salt is obtained after 2h of reaction;
the reaction equation is:
in the reaction process, 4.4' diaminodiphenylamine-2-sulfonic acid, hydrochloric acid and sodium nitrite undergo diazotization reaction to generate diazonium salt; in diazotization reaction, hydrochloric acid firstly dissolves 4.4 'diaminodiphenylamine-2-sulfonic acid, sodium nitrite is added to generate nitrous acid, and finally diazonium salt is generated by the action of the nitrous acid and 4.4' diaminodiphenylamine-2-sulfonic acid;
s2, one-time coupling
Preparing a 15% clev acid solution in a batching kettle, and then adding excessive sodium bicarbonate into the clev acid solution to prepare a prepared solution for later use;
adding sodium carbonate into diazotization mixed materials through an overhead tank, regulating the pH to be slightly acidic, controlling the reaction temperature to be 10-15 ℃, adding 8000kg of pre-prepared clevus acid solution under strong stirring, and carrying out a first coupling reaction for about 4 hours to obtain a first coupling product; in the primary coupling reaction of the step, the conversion rate of 4.4' diaminodiphenylamine-2-sulfonic acid diazonium salt is 93.5%;
the main reaction equation is:
2HCL+NaCO3＝2NaCL+H2O+CO2；
s3, secondary diazotization
Adding 30% hydrochloric acid solution and ice into the primary coupling material through a high-level tank, controlling the reaction temperature to be about 0 ℃, and then adding 30% sodium nitrite solution under the liquid level through a hose, wherein the reaction time is about 2 hours; diazotization reaction needs to keep the inside of the reaction kettle in an acidic environment;
the reaction equation is:
s4, secondary coupling
Adding a pre-prepared clev acid solution into the materials after the secondary diazotization reaction through an overhead tank, carrying out neutralization reaction on sodium bicarbonate in the solution and hydrogen chloride in the mixed materials, regulating the pH to be weak alkaline, controlling the reaction temperature to be 10-15 ℃, and carrying out secondary coupling reaction for about 2.5 hours;
the reaction equation is:
2HCL+NaCO3＝2NaCL+H2O+CO2；
s5, salting out, filter pressing and drying
Adding a certain amount of sodium chloride solid into the secondary coupling reaction mixture to precipitate and crystallize a coupling reaction product in the solution, then conveying the material into a filter press for filter pressing treatment, and conveying filtrate wastewater W5-1 containing sodium bicarbonate, sodium chloride, ammonium nitrite and the like to a factory sewage treatment station for treatment; the filter cake is a direct blending dark green wet product.
As a further scheme of the invention: the feeding mole ratio is 4.4' diaminodiphenylamine-2-sulfonic acid: hydrogen chloride = 1mol:4.8mol.
Compared with the prior art; the beneficial effects of the invention are as follows: the invention adopts 4.4' diaminodiphenylamine-2-sulfonic acid as raw material, and is prepared by diazotization, primary coupling, secondary diazotization, secondary coupling and purification processes, thus ensuring that the direct blending dark blue light is less poor and yellowish green, facilitating the subsequent market sales, not needing to use other dyes for color mixing and reducing the cost.
Detailed Description
In the description of the present invention, it should be noted that, unless explicitly stated and limited otherwise, the terms "mounted," "provided," "connected," and "connected" are to be construed broadly; for example, the connection may be fixed connection, detachable connection, or integral connection, mechanical connection, electrical connection, direct connection, indirect connection via an intermediate medium, or communication between two elements. The specific meaning of the above terms in the present invention will be understood in specific cases by those of ordinary skill in the art.
The direct blending dark blue is produced by adopting 4, 4' -diaminodiphenylamine-2-sulfonic acid as a raw material and adopting diazotization, primary coupling, secondary diazotization, secondary coupling and purification processes.
The method comprises the following steps:
s1, diazotizing
3000kg of water, 4000kg of ice, 1500kg of 4.4 '-diaminodiphenylamine-2-sulfonic acid and 3140kg of 30% hydrochloric acid solution are put into a closed reaction tank, the hydrochloric acid solution and the 4.4' -diaminodiphenylamine-2-sulfonic acid are added into a sulfonation kettle through a metering tank, beating and grinding are carried out for 0.5h at the temperature of about 0 ℃ in the kettle, 2500kg of prepared 30% sodium nitrite solution is added under the liquid level, and diazonium salt is obtained after 2h of reaction. In this diazotization reaction, the conversion of 4.4' diaminodiphenylamine-2-sulfonic acid was 98%.
The reaction equation is:
in the reaction process, 4.4' diaminodiphenylamine-2-sulfonic acid, hydrochloric acid and sodium nitrite undergo diazotization reaction to generate diazonium salt. In diazotization reaction, hydrochloric acid firstly dissolves 4.4 'diaminodiphenylamine-2-sulfonic acid, sodium nitrite is added to generate nitrous acid, and finally diazonium salt is generated by the action of the nitrous acid and 4.4' diaminodiphenylamine-2-sulfonic acid.
S2, one-time coupling
Preparing a 15% clev acid solution in a batching kettle, and then adding excessive sodium bicarbonate into the clev acid solution to prepare the prepared solution for standby.
Adding sodium carbonate into diazotization mixture through a high-level tank, regulating the pH to be slightly acidic, controlling the reaction temperature to be 10-15 ℃, adding 8000kg of pre-prepared clevus acid solution under strong stirring, and carrying out a first coupling reaction for about 4 hours to obtain a first coupling product. In the primary coupling reaction of the step, the conversion rate of 4.4' -diaminodiphenylamine-2-sulfonic acid diazonium salt is 93.5%.
The main reaction equation is:
2HCL+NaCO3＝2NaCL+H2O+CO2；
s3, secondary diazotization
Adding 30% hydrochloric acid solution and ice into the primary coupling material through a high-level tank, controlling the reaction temperature to be about 0 ℃, and then adding 30% sodium nitrite solution under the liquid level through a hose, wherein the reaction time is about 2 hours. The diazotization reaction needs to keep the inside of the reaction kettle in an acidic environment.
The reaction equation is:
s4, secondary coupling
Adding a pre-prepared clev acid solution into the materials after the secondary diazotization reaction through an overhead tank, carrying out neutralization reaction on sodium bicarbonate in the solution and hydrogen chloride in the mixed materials, regulating the pH to be weak alkaline, controlling the reaction temperature to be 10-15 ℃, and carrying out the secondary coupling reaction for about 2.5 hours.
The reaction equation is:
2HCL+NaCO3＝2NaCL+H2O+CO2；
s5, salting out, filter pressing and drying
Adding a certain amount of sodium chloride solid into the secondary coupling reaction mixture to precipitate and crystallize a coupling reaction product in the solution, then conveying the material into a filter press for filter pressing treatment, and conveying filtrate wastewater W5-1 containing sodium bicarbonate, sodium chloride, ammonium nitrite and the like to a factory sewage treatment station for treatment; the filter cake is a direct blending dark green wet product, and the water content is about 20%.
The optimal proportion of the product is as follows: 4,4 diaminodiphenylamine-2-sulfonic acid 1500, 30% hydrochloric acid solution 3140, clev acid 2400, clev acid 1150.
The method comprises the following steps: only 4 moles of acid are required for 1 mole of amino diazotization in the 4.4' diaminodiphenylamine-2-sulfonic acid diazotization reaction; however, in order for the reaction to proceed, the acid must be in an appropriate excess, the excess of acid being dependent on the basicity of the 4.4' diaminodiphenylamine-2-sulfonic acid. In the method, the feeding mole ratio is 4.4' diaminodiphenylamine-2-sulfonic acid: hydrogen chloride = 1mol:4.8mol.
Experimental or test data
Conclusion: by the adjustment method, the values of the subsequent color light values A and B are all within 0.5.
As would be apparent to one skilled in the art; it is obvious that the invention is not limited to the details of the above-described exemplary embodiments; and without departing from the spirit or essential characteristics of the invention; the invention can be embodied in other specific forms. Thus, the method comprises the steps of; from either point of view; the embodiments should be considered as exemplary; and is non-limiting; the scope of the invention is indicated by the appended claims rather than by the foregoing description; it is therefore intended to include within the invention all changes that fall within the meaning and range of equivalency of the claims.
Furthermore, it is provided that; it should be understood that; although the present description describes embodiments; but not every embodiment contains only one independent technical solution; this manner of description is for clarity only; the skilled artisan should recognize the specification as a whole; the technical solutions in the embodiments may also be combined appropriately; forming other embodiments as will be appreciated by those skilled in the art.
Claims (2)
1. The preparation method of the direct blending dark blue is characterized by comprising the following steps:
s1, diazotizing
3000kg of water, 4000kg of ice, 1500kg of 4.4 '-diaminodiphenylamine-2-sulfonic acid and 3140kg of 30% hydrochloric acid solution are put into a closed reaction tank, the hydrochloric acid solution and the 4.4' -diaminodiphenylamine-2-sulfonic acid are added into a sulfonation kettle through a metering tank, beating and grinding are carried out for 0.5h at the temperature of about 0 ℃ in the kettle, 2500kg of prepared 30% sodium nitrite solution is added under the liquid level, and diazonium salt is obtained after 2h of reaction;
the reaction equation is:
in the reaction process, 4.4' diaminodiphenylamine-2-sulfonic acid, hydrochloric acid and sodium nitrite undergo diazotization reaction to generate diazonium salt; in diazotization reaction, hydrochloric acid firstly dissolves 4.4 'diaminodiphenylamine-2-sulfonic acid, sodium nitrite is added to generate nitrous acid, and finally diazonium salt is generated by the action of the nitrous acid and 4.4' diaminodiphenylamine-2-sulfonic acid;
s2, one-time coupling
Preparing a 15% clev acid solution in a batching kettle, and then adding excessive sodium bicarbonate into the clev acid solution to prepare a prepared solution for later use;
adding sodium carbonate into diazotization mixed materials through an overhead tank, regulating the pH to be slightly acidic, controlling the reaction temperature to be 10-15 ℃, adding 8000kg of pre-prepared clevus acid solution under strong stirring, and carrying out a first coupling reaction for about 4 hours to obtain a first coupling product; in the primary coupling reaction of the step, the conversion rate of 4.4' diaminodiphenylamine-2-sulfonic acid diazonium salt is 93.5%;
the main reaction equation is:
2HCL+NaCO3＝2NaCL+H2O+CO2；
s3, secondary diazotization
Adding 30% hydrochloric acid solution and ice into the primary coupling material through a high-level tank, controlling the reaction temperature to be about 0 ℃, and then adding 30% sodium nitrite solution under the liquid level through a hose, wherein the reaction time is about 2 hours; diazotization reaction needs to keep the inside of the reaction kettle in an acidic environment;
the reaction equation is:
s4, secondary coupling
Adding a pre-prepared clev acid solution into the materials after the secondary diazotization reaction through an overhead tank, carrying out neutralization reaction on sodium bicarbonate in the solution and hydrogen chloride in the mixed materials, regulating the pH to be weak alkaline, controlling the reaction temperature to be 10-15 ℃, and carrying out secondary coupling reaction for about 2.5 hours;
the reaction equation is:
2HCL+NaCO3＝2NaCL+H2O+CO2；
s5, salting out, filter pressing and drying
Adding a certain amount of sodium chloride solid into the secondary coupling reaction mixture to precipitate and crystallize a coupling reaction product in the solution, then conveying the material into a filter press for filter pressing treatment, and conveying filtrate wastewater W5-1 containing sodium bicarbonate, sodium chloride, ammonium nitrite and the like to a factory sewage treatment station for treatment; the filter cake is a direct blending dark green wet product.
2. The method for preparing the direct blending navy blue according to claim 1, which is characterized in that the feeding mole ratio is 4.4' diaminodiphenylamine-2-sulfonic acid: hydrogen chloride = 1mol:4.8mo.
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| Application Number | Priority Date | Filing Date | Title |
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| CN202310152053.4A CN116102898A (en) | 2023-02-22 | 2023-02-22 | Preparation method of direct blending dark blue |
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| Application Number | Priority Date | Filing Date | Title |
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| CN202310152053.4A CN116102898A (en) | 2023-02-22 | 2023-02-22 | Preparation method of direct blending dark blue |
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Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63317569A (en) * | 1987-06-18 | 1988-12-26 | Canon Inc | Recording solution |
| RO111779B1 (en) * | 1994-01-05 | 1997-01-30 | Alexandru Constantinide | Preparation process for some non-benzidinic direct tetrakisazoic blue dyes |
| CN1193638A (en) * | 1997-03-13 | 1998-09-23 | 希巴特殊化学控股公司 | Azo dye mixtures, azo dyes, processes for their preparation, and their use |
| CN101307187A (en) * | 2008-07-09 | 2008-11-19 | 吴江梅堰三友染料化工有限公司 | Preparation process for directly blended spinning navy D-R dye |
| CN102408743A (en) * | 2011-08-10 | 2012-04-11 | 吴江梅堰三友染料化工有限公司 | Production process of direct blending navy blue D-R dye |
| CN111909536A (en) * | 2020-09-01 | 2020-11-10 | 浙江闰土染料有限公司 | Black direct dye composition, black direct dye and preparation method and application thereof |
| CN112358740A (en) * | 2020-11-06 | 2021-02-12 | 浙江闰土染料有限公司 | Navy blue direct dye and its preparation method and use |
-
2023
- 2023-02-22 CN CN202310152053.4A patent/CN116102898A/en active Pending
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63317569A (en) * | 1987-06-18 | 1988-12-26 | Canon Inc | Recording solution |
| RO111779B1 (en) * | 1994-01-05 | 1997-01-30 | Alexandru Constantinide | Preparation process for some non-benzidinic direct tetrakisazoic blue dyes |
| CN1193638A (en) * | 1997-03-13 | 1998-09-23 | 希巴特殊化学控股公司 | Azo dye mixtures, azo dyes, processes for their preparation, and their use |
| CN101307187A (en) * | 2008-07-09 | 2008-11-19 | 吴江梅堰三友染料化工有限公司 | Preparation process for directly blended spinning navy D-R dye |
| CN102408743A (en) * | 2011-08-10 | 2012-04-11 | 吴江梅堰三友染料化工有限公司 | Production process of direct blending navy blue D-R dye |
| CN111909536A (en) * | 2020-09-01 | 2020-11-10 | 浙江闰土染料有限公司 | Black direct dye composition, black direct dye and preparation method and application thereof |
| CN112358740A (en) * | 2020-11-06 | 2021-02-12 | 浙江闰土染料有限公司 | Navy blue direct dye and its preparation method and use |
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