CN1900171A - Direct blended rose red dye and preparation process thereof - Google Patents
Direct blended rose red dye and preparation process thereof Download PDFInfo
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- CN1900171A CN1900171A CN 200610088172 CN200610088172A CN1900171A CN 1900171 A CN1900171 A CN 1900171A CN 200610088172 CN200610088172 CN 200610088172 CN 200610088172 A CN200610088172 A CN 200610088172A CN 1900171 A CN1900171 A CN 1900171A
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- aniline
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- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- 241000220317 Rosa Species 0.000 title claims description 28
- 239000001044 red dye Substances 0.000 title abstract 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims abstract description 57
- 238000006243 chemical reaction Methods 0.000 claims abstract description 53
- 239000000975 dye Substances 0.000 claims abstract description 52
- 238000002156 mixing Methods 0.000 claims abstract description 31
- 238000006482 condensation reaction Methods 0.000 claims abstract description 26
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 239000012954 diazonium Substances 0.000 claims description 13
- 150000001989 diazonium salts Chemical class 0.000 claims description 13
- 238000005516 engineering process Methods 0.000 claims description 13
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 12
- 235000017550 sodium carbonate Nutrition 0.000 claims description 12
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 12
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 claims description 9
- 238000003756 stirring Methods 0.000 claims description 7
- 235000010288 sodium nitrite Nutrition 0.000 claims description 6
- REJHVSOVQBJEBF-OWOJBTEDSA-N 5-azaniumyl-2-[(e)-2-(4-azaniumyl-2-sulfonatophenyl)ethenyl]benzenesulfonate Chemical compound OS(=O)(=O)C1=CC(N)=CC=C1\C=C\C1=CC=C(N)C=C1S(O)(=O)=O REJHVSOVQBJEBF-OWOJBTEDSA-N 0.000 claims description 5
- REJHVSOVQBJEBF-UHFFFAOYSA-N DSD-acid Natural products OS(=O)(=O)C1=CC(N)=CC=C1C=CC1=CC=C(N)C=C1S(O)(=O)=O REJHVSOVQBJEBF-UHFFFAOYSA-N 0.000 claims description 5
- 239000012065 filter cake Substances 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 4
- 238000009413 insulation Methods 0.000 claims description 4
- 239000010813 municipal solid waste Substances 0.000 claims description 4
- DPDMMXDBJGCCQC-UHFFFAOYSA-N [Na].[Cl] Chemical compound [Na].[Cl] DPDMMXDBJGCCQC-UHFFFAOYSA-N 0.000 claims description 3
- 238000013019 agitation Methods 0.000 claims description 3
- 238000003556 assay Methods 0.000 claims description 2
- 230000008034 disappearance Effects 0.000 claims description 2
- 238000004090 dissolution Methods 0.000 claims description 2
- 238000004809 thin layer chromatography Methods 0.000 claims description 2
- 238000004043 dyeing Methods 0.000 abstract description 16
- 229920000742 Cotton Polymers 0.000 abstract description 6
- 229920002678 cellulose Polymers 0.000 abstract description 3
- 239000001913 cellulose Substances 0.000 abstract description 3
- 239000000835 fiber Substances 0.000 abstract description 3
- 238000000034 method Methods 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 3
- 238000005265 energy consumption Methods 0.000 abstract description 2
- 239000002351 wastewater Substances 0.000 abstract description 2
- 229920000728 polyester Polymers 0.000 abstract 2
- 229920000297 Rayon Polymers 0.000 abstract 1
- 230000000711 cancerogenic effect Effects 0.000 abstract 1
- 231100000315 carcinogenic Toxicity 0.000 abstract 1
- 238000005859 coupling reaction Methods 0.000 abstract 1
- 238000004904 shortening Methods 0.000 abstract 1
- 239000003292 glue Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- PGJJYXPMHZOQHJ-UHFFFAOYSA-N 2-[1,2-diamino-2-(2-sulfophenyl)ethenyl]benzenesulfonic acid Chemical compound C=1C=CC=C(S(O)(=O)=O)C=1C(N)=C(N)C1=CC=CC=C1S(O)(=O)=O PGJJYXPMHZOQHJ-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical class CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 description 1
- 206010007247 Carbuncle Diseases 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- -1 aliphatics amine Chemical class 0.000 description 1
- POJOORKDYOPQLS-UHFFFAOYSA-L barium(2+) 5-chloro-2-[(2-hydroxynaphthalen-1-yl)diazenyl]-4-methylbenzenesulfonate Chemical compound [Ba+2].C1=C(Cl)C(C)=CC(N=NC=2C3=CC=CC=C3C=CC=2O)=C1S([O-])(=O)=O.C1=C(Cl)C(C)=CC(N=NC=2C3=CC=CC=C3C=CC=2O)=C1S([O-])(=O)=O POJOORKDYOPQLS-UHFFFAOYSA-L 0.000 description 1
- 238000003287 bathing Methods 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- ZIPLUEXSCPLCEI-UHFFFAOYSA-N cyanamide group Chemical group C(#N)[NH-] ZIPLUEXSCPLCEI-UHFFFAOYSA-N 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 239000000982 direct dye Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000002932 luster Substances 0.000 description 1
- 150000007974 melamines Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Coloring (AREA)
Abstract
A direct blending rose-red dye has a chemical structure shown in a formula , and the preparation process comprises a first condensation reaction, an aniline diazo reaction, a coupling reaction, a second condensation reaction and a third condensation reaction which are sequentially carried out, so that the direct blending rose-red dye is finally obtained; the dye does not contain carcinogenic chemicals prohibited by European countries such as Germany, is suitable for both cellulose dyeing and one-bath one-step dyeing of polyester/cotton, polyester/viscose and blended fibers, and has the advantages of reducing dyeing procedures, shortening dyeing time, reducing dyeing wastewater, reducing dyeing energy consumption, reducing dyeing cost and increasing yield.
Description
Technical field
The present invention relates generally to a kind of direct blend dye and preparation technology thereof.
Background technology
Directly the application of blend dye is extensive day by day, except that be used to wash/cotton, wash/glue the blending, also can be used for BLENDED FABRIC such as hair/sticking, brocade/sticking, nitrile/cotton, nitrile/glue.Developed at present the direct blending D type dye of 28 kinds, as yellow D-2RL, yellow D-3RNL, carbuncle D-BLL, navy D-R, brown D-RS etc., can be mixed with dispersed dye is used to wash/cotton, the one-bath dyeing washing/glue, also can be used for normal dyeing.Most of directly blend dye kind both can be used as direct blend dye and had used, and also can be used as direct fast dye and used.In this direct blending D type dye series of products, also lack a variety of chromatograms.
Summary of the invention
The purpose of this invention is to provide a kind of direct blending rose dye, replenish the rhodo chromatogram of direct blending D type dye series of products.
Another purpose of the present invention provides the preparation technology of described direct blending rose dye.
The present invention can be implemented by the following technical programs:
A kind of direct blending rose dye, it has following structural formula:
In the formula: R1=NH
2CH
2CH
2OH or
R
2=H or CH
3
Described R
2Be preferably H.
The present invention can also be implemented by the following technical programs:
A kind of preparation technology of direct blending rose dye, it may further comprise the steps:
(1), condensation reaction for the first time: after cyanuric chloride, ice, water mixing, make condenses for the first time with 1-amino-8 naphthols-3,6 disulfonic acid solution hybrid reaction again;
(2), aniline doazo reaction: with aniline and mixed in hydrochloric acid, mix with Sodium Nitrite again and carry out doazo reaction, generate diazonium salt of aniline;
(3), linked reaction: with described diazonium salt of aniline and described first time condenses carry out linked reaction and generate monoazo-dyes;
(4), condensation reaction for the second time: with 4,4 ' diaminostilbene-2,2 '-disulfonic acid and sodium hydroxide and water mixed dissolution after, generate the condenses second time with described monoazo-dyes hybrid reaction;
(5), condensation reaction for the third time: with 1, the 4-morpholine and described second time the condenses hybrid reaction obtain direct blending rose dye.
The described condensation reaction first time is: the cyanuric chloride of 18-19 weight part was joined in the trash ice of the water of 50-60 weight part and 80-100 weight part stirring to pulp 15-25 minute, temperature is 0-2 degree centigrade, drip 1-amino-8 naphthols-3 then, 6 disulfonic acid solution, temperature keeps 0-5 degree centigrade, keep the pH value 3-3.2 of reaction soln then with sodium carbonate solution, continue to react, make condenses for the first time to reaction end; Described 1-amino-8 naphthols-3,6 disulfonic acid solution is the water that is added the 170-180 weight part by 1-amino-8 naphthols-3,6 disulfonic acid of 34~36 weight parts, and adjusting pH value with sodium hydroxide solution again is 6-6.5, prepared solution.
Described aniline doazo reaction is: with the water of 9-10 weight part aniline and 20-30 weight part, and the concentration of 30-40 weight part is 30% mixed in hydrochloric acid and makes the aniline dissolving, add ice-cooled again to temperature 0-2 degree centigrade, adding 23-25 weight part concentration is 30% sodium nitrite solution in 20-30 minute, makes diazonium salt of aniline after the reaction.
Described linked reaction is: will be 6-7 with the sodium carbonate solution pH value that neutralizes at condenses condensation reaction obtains described first time first time, be added in the diazonium salt of aniline that obtains in the described aniline doazo reaction then, reaction is after 1.5-2.5 hour under temperature 0-5 degree centigrade, the condition of pH value 6-7, be transferred to pH value 8-8.5 with yellow soda ash again, continue to react 0.8-1.2 hour up to the diazonium salt of aniline disappearance, make the rose monoazo-dyes.
The described condensation reaction second time is: with 4 of 18-19 weight part, 4 ' diaminostilbene-2,2 '-water that disulfonic acid adds the 135-140 weight part stirs, regulate pH value to 7.8-8.2 with sodium hydroxide solution again, make 4,4 ' diaminostilbene-2,2 '-disulfonic acid all dissolves, then this solution is poured in the monoazo-dyes that makes in described linked reaction, progressively be warmed up to 39-40 degree centigrade again, at any time keep reaction soln pH value 7-7.5 with sodium carbonate solution, reacted 1.5-2.5 hour, make condenses for the second time.
Described condensation reaction for the third time is: with 1 of 9-10 weight part, the 4-morpholine joins and also under agitation heat to 93-98 degree centigrade in the condenses second time that makes in the described condensation reaction second time, insulation reaction 4-5 hour, with thin-layer chromatography after the assay was approved, be 30% the hydrochloric acid pH value 6-6.5 that neutralizes with concentration, and the 18-25% that presses reaction volume add sodium-chlor, dyestuff is analysed to the greatest extent, press filtration while hot gets filter cake, makes direct blending rose dye after the oven dry.
Compared with the prior art the present invention has following advantage: directly blending rose dye is that the reactive dyestuffs structure is screened by becoming the melamine class azo direct dye after the modification, and advantage comprises:
(1) be a melamine class azoic dyestuff according to the prepared direct blending rose of this technology, this dyestuff contains trimeric cyanamide in molecular structure, Mierocrystalline cellulose, fiber are had good avidity; They are by cyanuric chloride and the dyestuff with amino or the compound of phenyl ring or phenyl ring derivatives class condensation becoming trimeric cyanamide structure;
(2) this dyestuff is that a monoazo color bodies and cyanuric chloride use 4 again through condensation reaction, 4 ' diaminostilbene-2,2 '-disulfonic acid connects two monoazo color bodiess symmetry as linking agent, seal the dyestuff that the 3rd reactive chlorine generates with suitable aliphatics amine then, have that lovely luster, form and aspect stablely, water-fast are washed, the characteristics of anti-diffusion;
(3) because not being European countries such as Germany, employed raw material do not announce that within the scope of forbidding, it is safe therefore using;
(4) this dyestuff be applicable to wash/cotton, wash/glue one and bathe one and go on foot high temperature dyeing;
This dyestuff does not contain the cancer-causing chemicals that European countries such as Germany ban use of, it promptly be applicable to cellulose dyeing be applicable to again wash/cotton, wash/glue, bathing single stage method and dye of mixed fibre, has the minimizing dyeing process, shorten dyeing time, reduce dyeing waste-water, reduce dyeing energy consumption, reduce the dyeing cost and close the advantage that increases output.
Embodiment
Embodiment 1:
The preparation technology of direct blending rose D-FR dyestuff may further comprise the steps:
(1) condensation reaction for the first time: the cyanuric chloride of 0.1mol is joined in the trash ice of the water of 3.4mol and 80g, stirring to pulp 20 minutes, temperature is controlled at 0-2 degree centigrade, in 1.5 hours, drip 1-amino-8 naphthols-3 then, 6 disulfonic acid solution, described 1-amino-8 naphthols-3,6 disulfonic acid solution are 1-amino-8 naphthols-3 by 0.098mol, 6 disulfonic acid, join in the water of 12mol, adjusting temperature is 25-30 degree centigrade, and adding concentration is that 30% sodium hydroxide solution adjusting pH value is 6-6.5, and temperature remains on 0-5 degree centigrade, make 1-amino-8 naphthols-3, the solution that makes during the whole CL of 6 disulfonic acid is that 15% sodium carbonate solution keeps the pH value 3-3.2 of reaction with concentration then, continues reaction 3 hours, do spot test with the indicator paradimethy laminobenzaldehyde, do not have yellow demonstration and be reaction end, make the condenses first time of 1-amino-8 naphthols-3,6 disulfonic acid and cyanuric chloride;
(2) aniline doazo reaction: 0.098mol aniline is added 1.6mol water, the concentration that adds 0.024mol again is 30% hydrochloric acid, stirring makes the aniline dissolving, add trash ice again, being cooled to temperature is 0-2 degree centigrade, the Sodium Nitrite that added 0.098mol in 20-30 minute carries out doazo reaction then, and it is to add behind 30% solution that this Sodium Nitrite need be made into concentration again, continues reaction at temperature of reaction 0-2 degree centigrade then and makes diazonium salt of aniline after 0.5 hour;
(3) linked reaction: the diazonium salt of aniline that makes in the step (2) is joined fast cyanuric chloride and 1-amino-8 naphthols-3 that obtains in the step (1), in the condensation reaction first time thing of 6 disulfonic acid, and be that reaction solution is adjusted to pH value is 7.8-8.2 for 15% sodium carbonate solution with concentration, continue reaction and disappear for terminal point, make the rose monoazo-dyes up to diazonium salt of aniline; Described rose monoazo-dyes is actual to be reactive brilliant red X-4B;
(4) condensation reaction for the second time: with 4 of 0.5mol, 4 ' diaminostilbene-2,2 '-water that disulfonic acid adds 8mol stirs, regulate pH value to 7.8-8.2 with sodium hydroxide solution again, make 4,4 ' diaminostilbene-2,2 '-disulfonic acid all dissolves, then this solution is poured into fast in the rhodo monoazo-dyes in the above-mentioned steps (3), in 0.5 hour, progressively be warmed up to 39-40 degree centigrade, at any time keep reaction soln pH value 7-7.5 with sodium carbonate solution, condensation reaction 2 hours obtains condenses for the second time; Described second time condenses actual be reactive red KD-8B;
(5) condensation reaction for the third time: with 1 of 0.115mol, the 4-morpholine joins second time of obtaining in the above-mentioned steps (4) in the condenses, under agitation heat to 95-98 degree centigrade, insulation reaction 2.5 hours, in 0.5 hour, add concentration then and be 15% sodium carbonate solution, pH value is transferred to 8.5, continued insulation reaction 2 hours, determine reaction end with chromatography, make direct blending rose;
(6) saltout, press filtration, oven dry: after condensation reaction for the third time finishes, be cooled to 80-90 degree centigrade, with concentration is that 30% hydrochloric acid is adjusted reaction solution pH value to 6, adding concentration by the 18-25% of reaction volume then is 23% industrial sodium-chlor, dyestuff is analysed to the greatest extent, be cooled to 60-65 degree centigrade, carry out press filtration and get filter cake, filter cake is made the blending rose of the finished product-directly after drying stdn then at 85-90 degree centigrade
Red D-FR, its molecular formula is:
Claims (9)
3, direct blending rose dye according to claim 1 is characterized in that: described R
2Be H.
4, a kind of preparation technology of direct blending rose dye, it is characterized in that: it may further comprise the steps:
(1), condensation reaction for the first time: after cyanuric chloride, ice, water mixing, make condenses for the first time with 1-amino-8 naphthols-3,6 disulfonic acid solution hybrid reaction again;
(2), aniline doazo reaction: with aniline and mixed in hydrochloric acid, mix with Sodium Nitrite again and carry out doazo reaction, generate diazonium salt of aniline;
(3), linked reaction: with described diazonium salt of aniline and described first time condenses carry out linked reaction and generate monoazo-dyes;
(4), condensation reaction for the second time: with 4,4 ' diaminostilbene-2,2 '-disulfonic acid and sodium hydroxide and water mixed dissolution after, generate the condenses second time with described monoazo-dyes hybrid reaction;
(5), condensation reaction for the third time: with 1, the 4-morpholine and described second time the condenses hybrid reaction obtain direct blending rose dye.
5, the preparation technology of direct blending rose dye according to claim 4, it is characterized in that: the described condensation reaction first time is: the cyanuric chloride of 18-19 weight part was joined in the trash ice of the water of 50-60 weight part and 80-100 weight part stirring to pulp 15-25 minute, temperature is 0-2 degree centigrade, drip 1-amino-8 naphthols-3 then, 6 disulfonic acid solution, temperature keeps 0-5 degree centigrade, the pH value 3-3.2 that keeps reaction soln then with sodium carbonate solution, continue to react to reaction end, make condenses for the first time; Described 1-amino-8 naphthols-3,6 disulfonic acid solution is the water that is added the 170-180 weight part by 1-amino-8 naphthols-3,6 disulfonic acid of 34~36 weight parts, and adjusting pH value with sodium hydroxide solution again is 6-6.5, prepared solution.
6, the preparation technology of direct blending rose dye according to claim 4, it is characterized in that: described aniline doazo reaction is: with the water of 9-10 weight part aniline and 20-30 weight part, and the concentration of 30-40 weight part is 30% mixed in hydrochloric acid and makes the aniline dissolving, add ice-cooled again to temperature 0-2 degree centigrade, adding 23-25 weight part concentration is 30% sodium nitrite solution in 20-30 minute, makes diazonium salt of aniline after the reaction.
7, the preparation technology of direct blending rose dye according to claim 4, it is characterized in that: described linked reaction is: will be 6-7 with the sodium carbonate solution pH value that neutralizes at condenses condensation reaction obtains described first time first time, be added in the diazonium salt of aniline that obtains in the described aniline doazo reaction then, reaction is after 1.5-2.5 hour under temperature 0-5 degree centigrade, the condition of pH value 6-7, be transferred to pH value 8-8.5 with yellow soda ash again, continue to react 0.8-1.2 hour up to the diazonium salt of aniline disappearance, make the rose monoazo-dyes.
8, the preparation technology of direct blending rose dye according to claim 4, it is characterized in that: the described condensation reaction second time is: with 4 of 18-19 weight part, 4 ' diaminostilbene-2,2 '-water that disulfonic acid adds the 135-140 weight part stirs, regulate pH value to 7.8-8.2 with sodium hydroxide solution again, make 4,4 ' diaminostilbene-2,2 '-disulfonic acid all dissolves, then this solution is poured in the monoazo-dyes that makes in described linked reaction, progressively be warmed up to 39-40 degree centigrade again, keep reaction soln pH value 7-7.5 with sodium carbonate solution at any time, reacted 1.5-2.5 hour, and made condenses for the second time.
9, the preparation technology of direct blending rose dye according to claim 4, it is characterized in that: described condensation reaction for the third time is: with 1 of 9-10 weight part, the 4-morpholine joins and also under agitation heat to 93-98 degree centigrade in the condenses second time that makes in the described condensation reaction second time, insulation reaction 4-5 hour, with thin-layer chromatography after the assay was approved, with concentration is 30% the hydrochloric acid pH value 6-6.5 that neutralizes, and the 18-25% that presses reaction volume adds sodium-chlor, dyestuff is analysed to the greatest extent, press filtration while hot, get filter cake, make direct blending rose dye after the oven dry.
Priority Applications (1)
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CN 200610088172 CN1900171A (en) | 2006-06-28 | 2006-06-28 | Direct blended rose red dye and preparation process thereof |
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CN 200610088172 CN1900171A (en) | 2006-06-28 | 2006-06-28 | Direct blended rose red dye and preparation process thereof |
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Family
ID=37656170
Family Applications (1)
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101580651B (en) * | 2009-03-31 | 2012-09-19 | 天津市亚东化工染料厂 | Pollution-free preparation technology of direct rose FR |
CN103193702A (en) * | 2013-04-18 | 2013-07-10 | 陕西师范大学 | Functionalization method for nitrogenous heterocyclic compound |
CN115612308A (en) * | 2022-09-08 | 2023-01-17 | 浙江闰土染料有限公司 | Preparation method and application of yellow direct blending dye |
-
2006
- 2006-06-28 CN CN 200610088172 patent/CN1900171A/en active Pending
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101580651B (en) * | 2009-03-31 | 2012-09-19 | 天津市亚东化工染料厂 | Pollution-free preparation technology of direct rose FR |
CN103193702A (en) * | 2013-04-18 | 2013-07-10 | 陕西师范大学 | Functionalization method for nitrogenous heterocyclic compound |
CN103193702B (en) * | 2013-04-18 | 2014-12-24 | 陕西师范大学 | Functionalization method for nitrogenous heterocyclic compound |
CN115612308A (en) * | 2022-09-08 | 2023-01-17 | 浙江闰土染料有限公司 | Preparation method and application of yellow direct blending dye |
CN115612308B (en) * | 2022-09-08 | 2023-11-17 | 浙江闰土染料有限公司 | Preparation method and application of yellow direct blending dye |
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