CN116751464A - Liquid blue dye composition and preparation method thereof - Google Patents
Liquid blue dye composition and preparation method thereof Download PDFInfo
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- CN116751464A CN116751464A CN202310607854.5A CN202310607854A CN116751464A CN 116751464 A CN116751464 A CN 116751464A CN 202310607854 A CN202310607854 A CN 202310607854A CN 116751464 A CN116751464 A CN 116751464A
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- 239000007788 liquid Substances 0.000 title claims abstract description 48
- 239000001045 blue dye Substances 0.000 title claims abstract description 26
- 239000000203 mixture Substances 0.000 title claims abstract description 24
- 238000002360 preparation method Methods 0.000 title claims abstract description 24
- 239000000975 dye Substances 0.000 claims abstract description 28
- 239000003381 stabilizer Substances 0.000 claims abstract description 23
- 239000003906 humectant Substances 0.000 claims abstract description 9
- 239000002994 raw material Substances 0.000 claims abstract description 9
- 239000003755 preservative agent Substances 0.000 claims abstract description 7
- 230000002335 preservative effect Effects 0.000 claims abstract description 7
- 239000003054 catalyst Substances 0.000 claims description 32
- 238000000108 ultra-filtration Methods 0.000 claims description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 239000000243 solution Substances 0.000 claims description 12
- 239000000706 filtrate Substances 0.000 claims description 11
- 238000010438 heat treatment Methods 0.000 claims description 11
- 239000012528 membrane Substances 0.000 claims description 11
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 10
- 239000012466 permeate Substances 0.000 claims description 10
- 239000001632 sodium acetate Substances 0.000 claims description 10
- 235000017281 sodium acetate Nutrition 0.000 claims description 10
- 238000001914 filtration Methods 0.000 claims description 9
- 238000001728 nano-filtration Methods 0.000 claims description 9
- 238000003756 stirring Methods 0.000 claims description 9
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 8
- 238000009833 condensation Methods 0.000 claims description 8
- 230000005494 condensation Effects 0.000 claims description 8
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 claims description 8
- 238000004811 liquid chromatography Methods 0.000 claims description 8
- 230000002378 acidificating effect Effects 0.000 claims description 7
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 claims description 6
- JLPULHDHAOZNQI-ZTIMHPMXSA-N 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC JLPULHDHAOZNQI-ZTIMHPMXSA-N 0.000 claims description 6
- BQGRVFPPZJPWPB-UHFFFAOYSA-N 3-[(n-ethylanilino)methyl]benzenesulfonic acid Chemical compound C=1C=CC=CC=1N(CC)CC1=CC=CC(S(O)(=O)=O)=C1 BQGRVFPPZJPWPB-UHFFFAOYSA-N 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 6
- QOSATHPSBFQAML-UHFFFAOYSA-N hydrogen peroxide;hydrate Chemical compound O.OO QOSATHPSBFQAML-UHFFFAOYSA-N 0.000 claims description 6
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 6
- 238000000926 separation method Methods 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- 229940083466 soybean lecithin Drugs 0.000 claims description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 5
- 239000004202 carbamide Substances 0.000 claims description 5
- 230000001276 controlling effect Effects 0.000 claims description 5
- 229910052708 sodium Inorganic materials 0.000 claims description 5
- 239000011734 sodium Substances 0.000 claims description 5
- 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 description 4
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 4
- 238000005086 pumping Methods 0.000 claims description 4
- 238000010992 reflux Methods 0.000 claims description 4
- 238000005406 washing Methods 0.000 claims description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 239000003109 Disodium ethylene diamine tetraacetate Substances 0.000 claims description 2
- ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 claims description 2
- 239000005913 Maltodextrin Substances 0.000 claims description 2
- 229920002774 Maltodextrin Polymers 0.000 claims description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims description 2
- 229930006000 Sucrose Natural products 0.000 claims description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 2
- XIKQZKVNIGCOIS-UHFFFAOYSA-N [Na].[Na].[Na].[Na].[Na].NCCN Chemical compound [Na].[Na].[Na].[Na].[Na].NCCN XIKQZKVNIGCOIS-UHFFFAOYSA-N 0.000 claims description 2
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 claims description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 claims description 2
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 2
- 238000010790 dilution Methods 0.000 claims description 2
- 239000012895 dilution Substances 0.000 claims description 2
- 235000019301 disodium ethylene diamine tetraacetate Nutrition 0.000 claims description 2
- 239000000194 fatty acid Substances 0.000 claims description 2
- 229930195729 fatty acid Natural products 0.000 claims description 2
- 150000002334 glycols Chemical class 0.000 claims description 2
- 229940035034 maltodextrin Drugs 0.000 claims description 2
- 229920002401 polyacrylamide Polymers 0.000 claims description 2
- 229920005862 polyol Polymers 0.000 claims description 2
- 150000003077 polyols Chemical class 0.000 claims description 2
- 230000001105 regulatory effect Effects 0.000 claims description 2
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 claims description 2
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 claims description 2
- 239000001509 sodium citrate Substances 0.000 claims description 2
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 claims description 2
- 235000011083 sodium citrates Nutrition 0.000 claims description 2
- 239000005720 sucrose Substances 0.000 claims description 2
- -1 sucrose fatty acid ester Chemical class 0.000 claims description 2
- 239000000230 xanthan gum Substances 0.000 claims description 2
- 229920001285 xanthan gum Polymers 0.000 claims description 2
- 229940082509 xanthan gum Drugs 0.000 claims description 2
- 235000010493 xanthan gum Nutrition 0.000 claims description 2
- 229910001385 heavy metal Inorganic materials 0.000 abstract description 10
- 239000003814 drug Substances 0.000 abstract description 7
- 229940079593 drug Drugs 0.000 abstract description 7
- 235000013305 food Nutrition 0.000 abstract description 7
- 150000002500 ions Chemical class 0.000 abstract description 6
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract description 3
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical group OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 238000001514 detection method Methods 0.000 description 6
- 239000011790 ferrous sulphate Substances 0.000 description 5
- 235000003891 ferrous sulphate Nutrition 0.000 description 5
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000001003 triarylmethane dye Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZJDNZLICJKXVIG-UHFFFAOYSA-N C=C.[Na].[Na].[Na].[Na].[Na] Chemical group C=C.[Na].[Na].[Na].[Na].[Na] ZJDNZLICJKXVIG-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 230000007547 defect Effects 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 229920006052 Chinlon® Polymers 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 2
- 239000004299 sodium benzoate Substances 0.000 description 2
- 235000010234 sodium benzoate Nutrition 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- CHHHXKFHOYLYRE-UHFFFAOYSA-M 2,4-Hexadienoic acid, potassium salt (1:1), (2E,4E)- Chemical compound [K+].CC=CC=CC([O-])=O CHHHXKFHOYLYRE-UHFFFAOYSA-M 0.000 description 1
- KMHZPJNVPCAUMN-UHFFFAOYSA-N Erbon Chemical compound CC(Cl)(Cl)C(=O)OCCOC1=CC(Cl)=C(Cl)C=C1Cl KMHZPJNVPCAUMN-UHFFFAOYSA-N 0.000 description 1
- HMEKVHWROSNWPD-UHFFFAOYSA-N Erioglaucine A Chemical compound [NH4+].[NH4+].C=1C=C(C(=C2C=CC(C=C2)=[N+](CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=2C(=CC=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S([O-])(=O)=O)=C1 HMEKVHWROSNWPD-UHFFFAOYSA-N 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- WAEMQWOKJMHJLA-UHFFFAOYSA-N Manganese(2+) Chemical compound [Mn+2] WAEMQWOKJMHJLA-UHFFFAOYSA-N 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 239000001001 arylmethane dye Substances 0.000 description 1
- 235000012745 brilliant blue FCF Nutrition 0.000 description 1
- 239000004161 brilliant blue FCF Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 208000012839 conversion disease Diseases 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 229960002089 ferrous chloride Drugs 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical group Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 1
- 239000002932 luster Substances 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 229910001437 manganese ion Inorganic materials 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- MCLZMWVEJOJWRA-UHFFFAOYSA-I pentasodium;pentaacetate Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O MCLZMWVEJOJWRA-UHFFFAOYSA-I 0.000 description 1
- 239000004302 potassium sorbate Substances 0.000 description 1
- 235000010241 potassium sorbate Nutrition 0.000 description 1
- 229940069338 potassium sorbate Drugs 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012360 testing method 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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0083—Solutions of dyes
-
- 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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0077—Preparations with possibly reduced vat, sulfur or indigo dyes
- C09B67/0078—Preparations of vat, sulfur or indigo dyes in liquid form
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to the technical field of C07C303/32, in particular to a liquid blue dye composition and a preparation method thereof, wherein the preparation raw materials at least comprise the following components in parts by weight: blue liquid dye: 900-1000 parts of humectant: 10-20 parts of pH stabilizer: 3-8 parts of preservative: 0.5-1.5 parts; the blue dye composition has improved storage stability by optimizing the blue dye preparation process and matching with other raw materials, and the contents of heavy metal ions and sulfate ions in the composition are effectively reduced, so that the use requirements of the fields of foods and medicines are met.
Description
Technical Field
The invention relates to the technical field of C07C303/32, in particular to a liquid blue dye composition and a preparation method thereof.
Background
The aryl methane dye is a dye containing a color development structure formed by substituting hydrogen in methane molecules with benzene or naphthalene, is the most widely used at present, and has the advantages of gorgeous color and luster, easy water solubility and easy processing, and is widely applied to dyeing and printing of wool, silk and chinlon, and is also widely applied to non-woven fields such as daily chemicals, agriculture chemicals, foods, medicines and the like. However, in the prior art data of CN102040853A, CN104327533A, CN105348846B disclosed at present, a heavy metal oxidation method is adopted to prepare the triarylmethane dye, and although the operation procedure of the heavy metal oxidation method is simple, the heavy metal of the product produced by the method cannot be eliminated, the defect of exceeding the standard of heavy metal ions exists, the manganese ion of the product index sold in the market at present is less than 200pppm, the produced product can only be used in the fields of dyeing of chinlon and wool fabrics, daily chemicals, agriculture chemicals and the like, but the hidden danger of heavy metal can be eliminated only by using a more complex treatment process in the fields of foods and medicines.
Disclosure of Invention
In order to solve the problems, the invention provides a liquid blue dye composition, which has improved storage stability by optimizing the preparation process of blue dye and matching with other raw materials, effectively reduces the contents of heavy metal ions and sulfate ions in the composition, and meets the use requirements in the fields of foods and medicines.
The invention provides a liquid blue dye composition, which is prepared from the following raw materials in parts by weight: blue liquid dye: 900-1000 parts of humectant: 10-20 parts of pH stabilizer: 3-8 parts of preservative: 0.5-1.5 parts.
As a preferred technical scheme, the preparation method of the blue liquid dye at least comprises the following steps:
(1) Adding the leuco into a reaction bottle, heating to 80-85 ℃, adding the catalyst and the stabilizer, and stirring for 20-40min;
(2) Cooling to 25-40deg.C, dropwise adding hydrogen peroxide water solution for controlled time, controlling pH to be acidic, and detecting endpoint by liquid chromatography;
(3) Regulating the system to alkaline pH, adding diatomite, stirring for 20-40min, and filtering to obtain filter residue and filtrate;
(4) Adding pure water into filtrate to fix volume, then carrying out ultrafiltration separation on the obtained diluent after constant dilution by the pure water to obtain ultrafiltration permeate, and carrying out nanofiltration concentration on the ultrafiltration permeate to obtain the blue liquid dye.
Preferably, the preparation method of the leuco body comprises the following steps: adding water, N-ethyl-N- (3' -sulfobenzyl) aniline, sodium o-sulfonate benzaldehyde and urea into a condensation pot, heating to 98-102 ℃, reacting to an end point under 0.1-0.15 MPa, and adding pure water until the solid content reaches 28-32%, thus obtaining the leuco.
Further preferably, the preparation method of the leuco body comprises the following steps: 136kg of water, 123kg of N-ethyl-N- (3' -sulfobenzyl) aniline, 45kg of sodium o-sulfonate benzaldehyde and 27kg of urea are added into a 500L condensation pot, the temperature is raised to 98-102 ℃, the reaction is carried out under 0.1-0.15 MPa until the end point is reached, and pure water is added until the solid content reaches 28-32%, thus obtaining the leuco.
The determination standard of the end point is liquid chromatography detection: the graph shows that the residual quantity of the N-ethyl-N- (3' -sulfobenzyl) aniline is lower than 1 percent, and the reaction end point is reached.
Preferably, the preparation method of the catalyst comprises the following steps: adding methanol, sodium acetate and o-phenylenediamine into a condensation pot, stirring and dissolving, adding ferrous salt, heating to 50-60 ℃, then dropwise adding isoxazole, heating and refluxing for reaction, preserving heat to a terminal point, cooling, filtering, washing with water, and pumping to obtain the catalyst.
Preferably, the ferrous salt is ferrous chloride or ferrous sulfate.
Further preferably, the preparation method of the catalyst comprises the following steps: adding 110kg of methanol, 30kg of sodium acetate and 24kg of o-phenylenediamine into a 250L condensation pot, stirring and dissolving, adding 45kg of ferrous sulfate for crystallization, heating to 50-60 ℃, dropwise adding 60kg of isoxazole, heating and refluxing for reaction, preserving heat to a terminal point, cooling, filtering, washing with water, and pumping to obtain the catalyst.
As a preferable technical scheme, the addition amount of the catalyst is 0.2-1wt% of the leuco body; the mass ratio of the catalyst to the aqueous hydrogen peroxide solution is 1: (23-50).
According to the invention, methanol, sodium acetate, o-phenylenediamine, ferrous sulfate and isoxazole are used as raw materials to prepare the catalyst, the catalytic leuco body and the aqueous hydrogen peroxide solution are reacted under an acidic condition and then treated to prepare the liquid blue dye, so that the traditional triarylmethane dye manganese dioxide oxidation synthesis process is effectively replaced, the defect that heavy metal ions exceed the standard caused by the process is effectively overcome, and the application range of the triarylmethane dye in the fields of foods and medicines is enlarged. The inventor finds that by controlling the proportion of the catalyst, the leuco body and the hydrogen peroxide water solution in the system in the research process, especially when the addition amount of the catalyst is 0.2-1wt% of the leuco body, the mass ratio of the catalyst to the hydrogen peroxide water solution is 1: (23-50) ensuring that the leuco in the system can be completely peroxidized by hydrogen peroxide as much as possible, thereby ensuring that the strength of the liquid dye synthesized by the leuco under the new process conditions reaches 165 percent.
Preferably, the mass ratio of the catalyst to the stabilizer is (1-2): 1.
preferably, the stabilizer is at least one selected from disodium ethylenediamine tetraacetate, pentasodium ethylenediamine triamine pentaate, polyacrylamide, soybean lecithin, xanthan gum, sodium carboxymethyl cellulose, sucrose fatty acid ester, and maltodextrin. Preferably, the stabilizer is pentasodium ethylene diamine pentanate or soybean lecithin.
The catalyst prepared based on the system of the invention adopts the pentasodium ethylene triamine penta-ate or the soybean lecithin as the stabilizer, especially when the mass ratio of the catalyst to the stabilizer in the system is (1-2): 1, the problems of blue liquid dye quality and yield reduction caused by unstable activity of the catalyst are effectively solved. The inventors analyzed the cause may be: the presence of pentasodium acetate or soybean lecithin can effectively ensure the activity of the catalyst prepared in the system, so that the leuco in the system can stably react with the hydrogen peroxide aqueous solution, and the reaction conversion rate is effectively improved.
Preferably, the dripping time is 1-2h. Preferably, the concentration of the aqueous hydrogen oxide solution is 10-15wt%. Preferably, the acidic pH is from 1.5 to 2.0. The liquid chromatography detection end point is that the residual quantity of leuco bodies is 1-2wt%.
Preferably, the alkaline pH is 8.5 to 9.5.
Preferably, the solids content of the diluent is 20-25%.
Preferably, the ultrafiltration separation specifically comprises: ultrafiltering with ultrafilter membrane at 20-50 deg.c and pressure of 1-2 MPa to ultrafiltrate conductivity less than 35000 μs/cm.
Preferably, the molecular weight cut-off of the ultrafiltration membrane is 1000-5000.
Preferably, the nanofiltration concentration specifically comprises: concentrating the ultrafiltration permeate by adopting a nanofiltration membrane until the solid content is 45-50%.
Preferably, the molecular weight cut-off of the nanofiltration membrane is 200-1000.
Based on the system, in the preparation process of the blue liquid dye, the filtrate obtained after filtration is subjected to further ultrafiltration operation, particularly ultrafiltration membrane is adopted to carry out ultrafiltration until the conductivity of ultrafiltration permeate of the diluent is less than 35000 mu s/cm under the conditions of 20-50 ℃ and 1-2 MPa, so that the influence of residual salt and impurities in the system on the strength of the blue liquid dye is avoided.
As a preferable technical scheme, the pH stabilizer is at least one selected from triethanolamine, sodium bicarbonate, sodium acetate and sodium citrate; preferably, the pH stabilizer is sodium acetate. Based on the system, 3-8 parts of the pH stabilizer is added, especially when the pH stabilizer is sodium acetate, the storage stability of the product is effectively improved, and the problem of pH reduction of the product caused by unstable blue liquid dye in the system in the long-time storage process is avoided.
As a preferred technical scheme, the preservative is at least one selected from potassium sorbate, sodium benzoate, parahydroxybenzoates, kaleidosteine YL-120, mo Lijing YL-103 and Mo Lijing YL-TBLplus; preferably, the preservative is sodium benzoate.
As a preferable technical scheme, the humectant is selected from at least one of water-soluble polyols, cellosolves, carbitol or glycol esters; preferably, the humectant is ethylene glycol. Based on the system of the invention, 10-20 parts of ethylene glycol is introduced to maintain the water balance of the liquid blue dye composition, so that the storage stability of the system is ensured.
In another aspect of the present invention, there is provided a method of preparing a liquid blue dye composition comprising at least the steps of: mixing the blue liquid dye, the humectant, the pH stabilizer and the preservative according to parts by weight.
Advantageous effects
1. The invention provides a liquid blue dye composition, which has improved storage stability by optimizing a blue dye preparation process and matching with other raw materials, effectively reduces the contents of heavy metal ions and sulfate ions in the composition, and meets the use requirements in the fields of foods and medicines.
2. According to the invention, methanol, sodium acetate, o-phenylenediamine, ferrous sulfate and isoxazole are used as raw materials to prepare the catalyst, the catalytic leuco body and the aqueous hydrogen peroxide solution are reacted under an acidic condition and then treated to prepare the liquid blue dye, so that the traditional triarylmethane dye manganese dioxide oxidation synthesis process is effectively replaced, the defect that heavy metal ions exceed the standard caused by the process is effectively overcome, and the application range of the triarylmethane dye in the fields of foods and medicines is enlarged.
3. The invention controls the proportion of the catalyst, the leuco and the hydrogen peroxide water solution in the system, especially when the addition amount of the catalyst is 0.2-1wt% of the leuco, and the mass ratio of the catalyst to the hydrogen peroxide water solution is 1: (23-50) ensuring that the leuco in the system can be completely peroxidized by hydrogen peroxide as much as possible, thereby ensuring that the strength of the liquid dye synthesized by the leuco under the new process conditions reaches 165 percent.
4. Based on the system, the catalyst prepared based on the system adopts pentasodium ethylene triamine penta-sodium or soybean lecithin as a stabilizer, and particularly when the mass ratio of the catalyst to the stabilizer in the system is (1-2): 1, the problems of blue liquid dye quality and yield reduction caused by unstable activity of the catalyst are effectively solved.
5. Based on the system, in the preparation process of the blue liquid dye, the filtrate obtained after filtration is subjected to further ultrafiltration operation, particularly ultrafiltration membrane is adopted to carry out ultrafiltration until the conductivity of ultrafiltration permeate of the diluent is less than 35000 mu s/cm under the conditions of 20-50 ℃ and 1-2 MPa, so that the influence of residual salt and impurities in the system on the strength of the blue liquid dye is avoided.
Detailed Description
Examples 1 to 3
Examples 1-3 of the present invention provide a liquid blue dye composition, the preparation raw materials of which are shown in Table 1, and the specific preparation method is as follows:
mixing blue liquid dye, humectant, pH stabilizer and antiseptic.
TABLE 1,
Wherein, the preparation method of the blue liquid dye in the embodiment 1-3 comprises the following steps:
(1) Adding the leuco into a reaction bottle, heating to 84 ℃, adding a catalyst and a stabilizer, and stirring for 30min;
(2) Cooling to 30 ℃, dropwise adding a hydrogen peroxide aqueous solution for controlled time, controlling a system of controlling the system to be acidic pH by 32wt% of sodium hydroxide aqueous solution, and detecting an end point by liquid chromatography;
(3) Adjusting the system to alkaline pH with sodium carbonate, adding diatomite, stirring for 30min, and filtering to obtain filter residue and filtrate;
(4) Adding pure water into filtrate to a constant volume of 3000mL, diluting the filtrate with 0.7 times of pure water (the volume of the filtrate) to obtain a diluent, performing ultrafiltration separation to obtain an ultrafiltration permeate, and performing nanofiltration concentration on the ultrafiltration permeate to obtain the blue liquid dye.
The preparation method of the leuco body comprises the following steps: 136kg of water, 123kg of N-ethyl-N- (3' -sulfobenzyl) aniline, 45kg of sodium o-sulfonate benzaldehyde and 27kg of urea (urea) are added into a 500L condensation pot, the temperature is raised to 100 ℃, the reaction is carried out under 0.25MPa until the end point, and pure water is added until the solid content reaches 30%, thus obtaining the leuco.
The determination standard of the end point is liquid chromatography detection: the graph shows that the residual quantity of the N-ethyl-N- (3' -sulfobenzyl) aniline is lower than 1 percent, and the reaction end point is reached.
The preparation method of the catalyst comprises the following steps: 110kg of methanol, 30kg of sodium acetate and 24kg of o-phenylenediamine are added into a 250L condensation pot, stirred and dissolved, 45kg of ferrous sulfate is added for crystallization, the temperature is raised to 55 ℃, 60kg of isoxazole is added dropwise, the temperature is raised for reflux reaction, the temperature is kept to the end point, the temperature is reduced, filtration and water washing are carried out, and the catalyst is obtained after pumping.
The time of the dripping is 1.5h. The acidic pH is 2.0. The liquid chromatography detection end point is that the residual amount of the leuco body is 1wt%.
The alkaline pH was 9.0. The mass of the filter residue was 10g (example 1), 15g (example 2) and 11g (example 3).
The ultrafiltration separation is specifically as follows: ultrafiltering with ultrafiltration membrane (molecular weight cut-off 1000) at 25deg.C under 2MPa to give ultrafiltrate with conductivity of 30000 μs/cm.
The nanofiltration concentration is specifically as follows: the ultrafiltration permeate was concentrated to the blue liquid dye mass shown in table 1 using nanofiltration membranes (molecular weight cut-off of 300).
Comparative example 1
Comparative example 1 of the present invention provides a blue liquid dye and a preparation method thereof, which is specifically as follows:
2000g of leuco (0.8 mol) is put into a 5000mL reaction bottle, the temperature is reduced to 25 ℃, 90g of manganese dioxide (industrial manganese dioxide, the effective content of manganese dioxide is 90 wt%) is added for 1 hour, the pH=2.5 of a system is controlled by 150g of 31wt% hydrochloric acid, the end point (the residual amount of the leuco is 1%) is detected by liquid chromatography, 10% of sodium carbonate by weight is added to the solution until the pH=9.0 after the end point is reached, the solution is stirred for 2 hours, the solution is filtered, the filter residue is 200g, the pH value of the filtrate is adjusted back (the pH=7 by 31% hydrochloric acid), the solution is diluted by 2.5 times of pure water constant volume, most byproducts and inorganic salts are firstly removed by an ultrafiltration membrane (the molecular weight cut-off is 1000), then the solution is diluted by 1 time of pure water constant volume, concentration treatment is continued by a nanofiltration membrane (the molecular weight cut-off is 300), and 868g of blue liquid dye is obtained after concentration.
Performance test method
The blue liquid dyes provided in examples and comparative example 1 were subjected to the following performance tests, test item results are shown in table 2.
Wherein, (1) the liquid strength is compared with the acid blue 9 standard (standard is the currently accepted strength in the market, the strength of the unified standard in the market is 200%, and the effective content is 60%) by referring to national standard GBT 6688-2008 (determination of relative dye strength and chromatic aberration-instrument method).
(2) The content of inorganic salt, the content of manganese and the content of iron are detected by sample feeding, in particular to detection by Tianxiang detection company.
(3) The strength of the folded powder is measured by referring to national standard GBT 6688-2008 (measurement of relative strength of dye and chromatic aberration-instrument method).
TABLE 2,
Claims (10)
1. The liquid blue dye composition is characterized by comprising the following preparation raw materials in parts by weight: blue liquid dye: 900-1000 parts of humectant: 10-20 parts of pH stabilizer: 3-8 parts of preservative: 0.5-1.5 parts.
2. A liquid blue dye composition according to claim 1, characterized in that the preparation method of the blue liquid dye comprises at least the following steps:
(1) Adding the leuco into a reaction bottle, heating to 80-85 ℃, adding the catalyst and the stabilizer, and stirring for 20-40min;
(2) Cooling to 25-40deg.C, dropwise adding hydrogen peroxide water solution for controlled time, controlling pH to be acidic, and detecting endpoint by liquid chromatography;
(3) Regulating the system to alkaline pH, adding diatomite, stirring for 20-40min, and filtering to obtain filter residue and filtrate;
(4) Adding pure water into filtrate to fix volume, then carrying out ultrafiltration separation on the obtained diluent after constant dilution by the pure water to obtain ultrafiltration permeate, and carrying out nanofiltration concentration on the ultrafiltration permeate to obtain the blue liquid dye.
3. A liquid blue dye composition according to claim 2, wherein the leuco body is prepared by the process of: adding water, N-ethyl-N- (3' -sulfobenzyl) aniline, sodium o-sulfonate benzaldehyde and urea into a condensation pot, heating to 98-102 ℃, reacting to an end point under 0.1-0.15 MPa, and adding pure water until the solid content reaches 28-32%, thus obtaining the leuco.
4. A liquid blue dye composition according to claim 2, wherein the catalyst is prepared by the process of: adding methanol, sodium acetate and o-phenylenediamine into a condensation pot, stirring and dissolving, adding ferrous salt, heating to 50-60 ℃, then dropwise adding isoxazole, heating and refluxing for reaction, preserving heat to a terminal point, cooling, filtering, washing with water, and pumping to obtain the catalyst.
5. A liquid blue dye composition according to claim 4, wherein said catalyst is added in an amount of 0.2 to 1wt% of leuco; the mass ratio of the catalyst to the aqueous hydrogen peroxide solution is 1: (23-50).
6. The liquid blue dye composition according to claim 5, wherein the mass ratio of the catalyst to the stabilizer is (1-2): 1, the stabilizer is at least one selected from disodium ethylenediamine tetraacetate, pentasodium ethylenediamine triamine pentaate, polyacrylamide, soybean lecithin, xanthan gum, sodium carboxymethyl cellulose, sucrose fatty acid ester and maltodextrin.
7. The liquid blue dye composition according to claim 6, wherein the ultrafiltration separation is specifically: ultrafiltering with ultrafilter membrane at 20-50 deg.c and pressure of 1-2 MPa to ultrafiltrate conductivity less than 35000 μs/cm.
8. A liquid blue dye composition according to claim 7, wherein said pH stabilizer is selected from at least one of triethanolamine, sodium bicarbonate, sodium acetate, sodium citrate.
9. The liquid blue dye composition according to claim 7, wherein said humectant is selected from at least one of water soluble polyols, cellosolves, carbitol or glycol esters.
10. A process for the preparation of a liquid blue dye composition according to any one of claims 1 to 9, comprising at least the steps of: mixing the blue liquid dye, the humectant, the pH stabilizer and the preservative according to parts by weight.
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| CN113105347A (en) * | 2021-04-09 | 2021-07-13 | 江苏华尔化工有限公司 | Environment-friendly and energy-saving process for synthesizing 1, 4-diamino-2, 3-dichloroanthraquinone |
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| GB332560A (en) * | 1929-04-22 | 1930-07-22 | Ig Farbenindustrie Ag | Process for the manufacture of new dyestuffs of the triphenyl methane series |
| CN101544864A (en) * | 2009-05-05 | 2009-09-30 | 上海乐美文具有限公司 | Pure blue gel ink and method for manufacturing same |
| CN107699048A (en) * | 2017-10-30 | 2018-02-16 | 华蓥市红军小学 | A kind of preparation method for easily wiping teaching ink |
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