CN116178983A - Preparation method of direct blending brown - Google Patents
Preparation method of direct blending brown Download PDFInfo
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- CN116178983A CN116178983A CN202310196741.0A CN202310196741A CN116178983A CN 116178983 A CN116178983 A CN 116178983A CN 202310196741 A CN202310196741 A CN 202310196741A CN 116178983 A CN116178983 A CN 116178983A
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- reaction
- sodium
- anilide
- solution
- coupling
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Links
- 238000002156 mixing Methods 0.000 title claims abstract description 21
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 46
- 238000006243 chemical reaction Methods 0.000 claims abstract description 39
- 238000005859 coupling reaction Methods 0.000 claims abstract description 39
- 150000003931 anilides Chemical class 0.000 claims abstract description 32
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims abstract description 32
- 230000008878 coupling Effects 0.000 claims abstract description 25
- 238000010168 coupling process Methods 0.000 claims abstract description 25
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims abstract description 20
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims abstract description 20
- 235000010288 sodium nitrite Nutrition 0.000 claims abstract description 16
- 239000012954 diazonium Substances 0.000 claims abstract description 14
- 239000000203 mixture Substances 0.000 claims abstract description 12
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims abstract description 11
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 11
- 239000011734 sodium Substances 0.000 claims abstract description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229910001868 water Inorganic materials 0.000 claims abstract description 11
- 239000000047 product Substances 0.000 claims abstract description 10
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims abstract description 10
- 235000017557 sodium bicarbonate Nutrition 0.000 claims abstract description 10
- 239000011780 sodium chloride Substances 0.000 claims abstract description 10
- 239000002253 acid Substances 0.000 claims abstract description 8
- 150000001989 diazonium salts Chemical class 0.000 claims abstract description 8
- 239000000463 material Substances 0.000 claims abstract description 8
- 238000003825 pressing Methods 0.000 claims abstract description 8
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims abstract description 6
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 4
- 238000001035 drying Methods 0.000 claims abstract description 4
- 239000012065 filter cake Substances 0.000 claims abstract description 4
- 239000011541 reaction mixture Substances 0.000 claims abstract description 4
- 238000005185 salting out Methods 0.000 claims abstract description 4
- 239000007787 solid Substances 0.000 claims abstract description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 18
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 18
- 230000001276 controlling effect Effects 0.000 claims description 10
- 238000006193 diazotization reaction Methods 0.000 claims description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
- 238000006386 neutralization reaction Methods 0.000 claims description 6
- 230000001105 regulatory effect Effects 0.000 claims description 6
- -1 anilide diazonium salt Chemical class 0.000 claims description 5
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 claims description 3
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 3
- CAMXVZOXBADHNJ-UHFFFAOYSA-N ammonium nitrite Chemical compound [NH4+].[O-]N=O CAMXVZOXBADHNJ-UHFFFAOYSA-N 0.000 claims description 3
- 229940051881 anilide analgesics and antipyretics Drugs 0.000 claims description 3
- 239000000706 filtrate Substances 0.000 claims description 3
- 238000000227 grinding Methods 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 238000004537 pulping Methods 0.000 claims description 3
- 239000010865 sewage Substances 0.000 claims description 3
- 229910000029 sodium carbonate Inorganic materials 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
- 239000000835 fiber Substances 0.000 claims 1
- 238000004043 dyeing Methods 0.000 abstract description 13
- 238000007639 printing Methods 0.000 abstract description 7
- 239000004753 textile Substances 0.000 abstract description 2
- 239000000975 dye Substances 0.000 description 5
- 239000002994 raw material Substances 0.000 description 3
- 238000011161 development Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000009940 knitting Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- 230000009286 beneficial effect Effects 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
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 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
- 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
- 238000000746 purification 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
- C09B35/02—Disazo dyes
- C09B35/039—Disazo dyes characterised by the tetrazo component
- C09B35/28—Disazo dyes characterised by the tetrazo component the tetrazo component containing two aryl nuclei linked by at least one of the groups —CON<, —SO2N<, —SO2—, or —SO2—O—
- C09B35/32—Disazo dyes characterised by the tetrazo component the tetrazo component containing two aryl nuclei linked by at least one of the groups —CON<, —SO2N<, —SO2—, or —SO2—O— from two different coupling components
Abstract
The invention discloses a preparation method of directly blended brown, and belongs to the field of textile printing and dyeing. The method comprises the following steps: s1, diazotizing, namely putting 3000kg of water, 4000kg of ice, 1560kg of anilide and 5500kg of 30% hydrochloric acid solution into a closed reaction tank, adding 3300kg of prepared 30% sodium nitrite solution, and reacting for 2 hours to obtain diazonium salt; s2, performing primary coupling, preparing 4500kg of 15% sodium metaaminobenzene sulfonate solution in a batching kettle, and adding excessive sodium bicarbonate; s3, secondary coupling; adding an r acid solution prepared in advance into the primary coupling mixture, and carrying out a secondary coupling reaction for about 3 hours; s4, salting out, filter pressing and drying; adding a certain amount of sodium chloride solid into the secondary coupling reaction mixture to precipitate and crystallize the coupling reaction product in the solution, and then sending the material into a filter press for filter pressing treatment, wherein the filter cake is a directly blended brown wet product. The invention can obtain good direct blending brown light, the direct blending brown light is brighter than standard, and the saturation of the colored light is brighter.
Description
Technical Field
The invention relates to the field of textile printing and dyeing, in particular to a preparation method of directly blending brown.
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 brown D-RS is prepared by adopting anilide as a raw material at present through diazotization, primary coupling, secondary coupling and purification processes. Is one of the main chromatograms of direct blending dyes, can be used for single-color dyeing, and can be used for mixed dyeing with other direct blending dyes, and has wide application range and large use amount.
The color light of the product prepared by the existing direct blending brown is darker than the standard, and the saturation of the color light is darker, so that the subsequent printing and dyeing effect is affected.
Disclosure of Invention
For the existing problems, the invention aims to provide a direct blending palm 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 brown comprises the following steps:
s1, diazotizing
Adding 3000kg of water, 4000kg of ice, 1560kg of anilide and 5500kg of 30% hydrochloric acid solution into a closed reaction tank, adding the hydrochloric acid solution and the anilide into a sulfonation kettle through a metering tank, controlling the temperature in the kettle to be about 0 ℃ for pulping and grinding, adding 3300kg of prepared 30% sodium nitrite solution under the liquid level through a hose, and reacting for 2 hours to obtain diazonium salt; the conversion of anilide in this step was about 98%;
the reaction equation is:
in the reaction process, diazotizing anilide, hydrochloric acid and sodium nitrite to generate anilide diazonium salt; in diazotization reaction, hydrochloric acid firstly dissolves anilide, sodium nitrite is generated by the sum of the anilides, and finally diazonium salt is generated by the action of the sodium nitrite and p-nitroaniline; therefore, although calculated according to the reaction equation, the reaction kettle is filled with a mixture of anilide diazonium salt, hydrogen chloride, sodium chloride, water, residual sodium nitrite and the like after the reaction is finished;
s2, one-time coupling
4500kg of 15% sodium metaaminobenzene sulfonate solution is prepared in a batching kettle, and then excessive sodium bicarbonate is added into the sodium metaaminobenzene sulfonate solution, so that the prepared solution is ready for use;
adding 30% sodium carbonate solution into diazotization mixture by an overhead tank, regulating the pH to be slightly acidic, controlling the reaction temperature to be 10-15 ℃, adding the pre-prepared sodium metaaminobenzenesulfonate solution under strong stirring, and carrying out a first coupling reaction to obtain a first coupling product after 1h of reaction; since the diazotization mixture contains excessive hydrogen chloride, the excessive hydrogen chloride can be subjected to neutralization reaction with sodium bicarbonate;
the reaction equation is:
s3, secondary coupling
Adding an r acid solution prepared in advance into the primary coupling mixed material, carrying out neutralization reaction on sodium bicarbonate in the solution and hydrogen chloride in the mixed material, regulating pH to be weak alkaline, controlling the reaction temperature to be 10-15 ℃, and carrying out secondary coupling reaction for about 3 hours;
the reaction equation is:
s4, 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 W4-1 containing sodium bicarbonate, sodium chloride and ammonium nitrite to a factory sewage treatment station for treatment; the filter cake is a direct blending brown wet product, and the water content is about 20%.
As still further aspects of the invention: the molar ratio of the anilide to the hydrogen chloride is 1mol of the anilide to 4.4mol of the hydrogen chloride.
As still further aspects of the invention: the secondary coupling is carried out by adjusting the pH of the medium to be 7.5-8, and controlling the temperature to be 10-15 ℃.
Compared with the prior art; the beneficial effects of the invention are as follows: the production of the direct blending brown is carried out by taking anilide as raw material, diazotizing, coupling once, coupling twice and purifying, obtaining good direct blending brown, and the direct blending brown has brighter color light than standard, brighter saturation of color light, and ensuring the effect of subsequent printing and dyeing.
Detailed Description
Embodiments of the present invention will be described below; the technical scheme in the embodiment of the invention is clearly and completely described; obviously; the described embodiments are only a few embodiments of the present invention; but not all embodiments. Based on the embodiments in the present invention; all other embodiments obtained by those skilled in the art without undue burden; all falling within the scope of the present invention.
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 preparation method of the direct blending brown comprises the steps of diazotizing anilide serving as a raw material, coupling once, coupling twice and purifying. The method comprises the following steps:
s1, diazotizing
Adding 3000kg of water, 4000kg of ice, 1560kg of anilide and 5500kg of 30% hydrochloric acid solution into a closed reaction tank, adding the hydrochloric acid solution and the anilide into a sulfonation kettle through a metering tank, controlling the temperature in the kettle to be about 0 ℃ for pulping and grinding, adding 3300kg of prepared 30% sodium nitrite solution under the liquid level through a hose, and reacting for 2 hours to obtain diazonium salt; the conversion of anilide in this step was about 98%.
The reaction equation is:
in the reaction process, diazotizing reaction is carried out on the anilide, hydrochloric acid and sodium nitrite, so as to generate the diazonium salt of the anilide. In diazotization reaction, hydrochloric acid firstly dissolves anilide, sodium nitrite is generated by the sum of the anilides, and finally diazonium salt is generated by the action of the sodium nitrite and p-nitroaniline. Thus, although calculated according to the reaction equation, after the reaction is completed, the reaction vessel is filled with a mixture of anilide diazonium salt, hydrogen chloride, sodium chloride, water, and the remaining sodium nitrite, etc.
S2, one-time coupling
4500kg of 15% sodium metaaminobenzene sulfonate solution is prepared in a batching kettle, and then excessive sodium bicarbonate is added into the sodium metaaminobenzene sulfonate solution, so that the prepared solution is ready for use.
Adding 30% sodium carbonate solution into diazotization mixture by a high-level tank, regulating the pH to be slightly acidic, controlling the reaction temperature to be 10-15 ℃, adding the pre-prepared sodium metaaminobenzenesulfonate solution under strong stirring, and carrying out a first coupling reaction to obtain a first coupling product after 1h of reaction. Since the diazotized mixture contains an excess of hydrogen chloride, the excess hydrogen chloride will undergo a neutralization reaction with sodium bicarbonate.
The reaction equation is:
2HCL+NaCO 3 ＝2NaCL+H 2 O+CO 2
s3, secondary coupling
Adding an r acid solution prepared in advance into the primary coupling mixture, carrying out neutralization reaction on sodium bicarbonate in the solution and hydrogen chloride in the mixture, regulating pH to be weak alkaline, controlling the reaction temperature to be 10-15 ℃, and carrying out secondary coupling reaction for about 3 hours.
The reaction equation is:
s4, 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 W4-1 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 brown wet product, and the water content is about 20%.
The optimal proportion of the product is as follows: 15.6 g of anilide, 55.00 g of 30% hydrochloric acid solution, 13.50 g of sodium metaaminobenzene sulfonate and 12.90 g of r acid
The method comprises the following steps: only 4 moles of acid are required for 1 mole of amino diazotisation in the anilide diazonium; 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 anilide. The molar ratio of anilide to hydrogen chloride was 1mol of anilide to 4.4mol of hydrogen chloride. In the secondary coupling, the medium is adjusted to pH=7.5-8 for coupling, and the temperature is controlled to be 10-15 ℃.
Experimental or test data.
Conclusion: the DL values are positive, the color is lighter and brighter, and the dye with positive C value is brighter and is favored by downstream products.
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. Any reference sign in a claim should not be construed as limiting the claim concerned.
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 (3)
1. The preparation method of the direct blending brown is characterized by comprising the following steps:
s1, diazotizing
Adding 3000kg of water, 4000kg of ice, 1560kg of anilide and 5500kg of 30% hydrochloric acid solution into a closed reaction tank, adding the hydrochloric acid solution and the anilide into a sulfonation kettle through a metering tank, controlling the temperature in the kettle to be about 0 ℃ for pulping and grinding, adding 3300kg of prepared 30% sodium nitrite solution under the liquid level through a hose, and reacting for 2 hours to obtain diazonium salt; the conversion of anilide in this step was about 98%;
the reaction equation is:
in the reaction process, diazotizing anilide, hydrochloric acid and sodium nitrite to generate anilide diazonium salt; in diazotization reaction, hydrochloric acid firstly dissolves anilide, sodium nitrite is generated by the sum of the anilides, and finally diazonium salt is generated by the action of the sodium nitrite and p-nitroaniline; therefore, although calculated according to the reaction equation, the reaction kettle is filled with a mixture of anilide diazonium salt, hydrogen chloride, sodium chloride, water, residual sodium nitrite and the like after the reaction is finished;
s2, one-time coupling
4500kg of 15% sodium metaaminobenzene sulfonate solution is prepared in a batching kettle, and then excessive sodium bicarbonate is added into the sodium metaaminobenzene sulfonate solution, so that the prepared solution is ready for use;
adding 30% sodium carbonate solution into diazotization mixture by an overhead tank, regulating the pH to be slightly acidic, controlling the reaction temperature to be 10-15 ℃, adding the pre-prepared sodium metaaminobenzenesulfonate solution under strong stirring, and carrying out a first coupling reaction to obtain a first coupling product after 1h of reaction; since the diazotization mixture contains excessive hydrogen chloride, the excessive hydrogen chloride can be subjected to neutralization reaction with sodium bicarbonate;
the reaction equation is:
2HCL+NaCO 3 ＝2NaCL+H 2 O+CO 2
s3, secondary coupling
Adding an r acid solution prepared in advance into the primary coupling mixed material, carrying out neutralization reaction on sodium bicarbonate in the solution and hydrogen chloride in the mixed material, regulating pH to be weak alkaline, controlling the reaction temperature to be 10-15 ℃, and carrying out secondary coupling reaction for about 3 hours;
the reaction equation is:
2HCL+NaCO 3 ＝2NaCL+H 2 O+CO 2 ；
s4, 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 W4-1 containing sodium bicarbonate, sodium chloride and ammonium nitrite to a factory sewage treatment station for treatment; the filter cake is a direct blending brown wet product, and the water content is about 20%.
2. The method for preparing the direct blending brown fiber according to claim 1, wherein the molar ratio of the anilide to the hydrogen chloride is 1mol of anilide to 4.4mol of hydrogen chloride.
3. The method for preparing the direct blending brown according to claim 1, wherein the secondary coupling is carried out by adjusting the medium to ph=7.5-8, and the temperature is controlled to be 10-15 ℃.
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| CN202310196741.0A CN116178983A (en) | 2023-03-03 | 2023-03-03 | Preparation method of direct blending brown |
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| Application Number | Priority Date | Filing Date | Title |
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| CN202310196741.0A CN116178983A (en) | 2023-03-03 | 2023-03-03 | Preparation method of direct blending brown |
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| CN116178983A true CN116178983A (en) | 2023-05-30 |
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| CN202310196741.0A Pending CN116178983A (en) | 2023-03-03 | 2023-03-03 | Preparation method of direct blending brown |
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101531831A (en) * | 2009-04-07 | 2009-09-16 | 吴江梅堰三友染料化工有限公司 | Production method of direct blended brown D-RS dye |
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- 2023-03-03 CN CN202310196741.0A patent/CN116178983A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101531831A (en) * | 2009-04-07 | 2009-09-16 | 吴江梅堰三友染料化工有限公司 | Production method of direct blended brown D-RS dye |
Non-Patent Citations (1)
| Title |
|---|
| 《最新染料使用大全》编写组: "《最新染料使用大全》", vol. 1, 31 August 1996, 中国纺织出版社, pages: 1249 * |
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