CN109293539A - A kind of raising dye fixing rate and the intermediate of solubility and preparation method thereof - Google Patents
A kind of raising dye fixing rate and the intermediate of solubility and preparation method thereof Download PDFInfo
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- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 239000000985 reactive dye Substances 0.000 claims abstract description 14
- 238000006243 chemical reaction Methods 0.000 claims description 24
- 239000007787 solid Substances 0.000 claims description 22
- 239000007788 liquid Substances 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 238000003756 stirring Methods 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 238000001914 filtration Methods 0.000 claims description 6
- 238000010792 warming Methods 0.000 claims description 6
- 238000004458 analytical method Methods 0.000 claims description 4
- 238000007599 discharging Methods 0.000 claims description 4
- -1 2- carboxyanilino Chemical group 0.000 claims description 3
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical class [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 claims description 3
- 235000010265 sodium sulphite Nutrition 0.000 claims description 3
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical class OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims 1
- 239000000975 dye Substances 0.000 abstract description 27
- 230000000694 effects Effects 0.000 abstract description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 6
- 238000006277 sulfonation reaction Methods 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 19
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 238000001514 detection method Methods 0.000 description 7
- 239000000835 fiber Substances 0.000 description 7
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 5
- 235000010288 sodium nitrite Nutrition 0.000 description 5
- 229950000244 sulfanilic acid Drugs 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 3
- 239000005711 Benzoic acid Substances 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 2
- 229910004727 OSO3H Inorganic materials 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000007710 freezing Methods 0.000 description 2
- 230000008014 freezing Effects 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- 238000009413 insulation Methods 0.000 description 2
- 229910052748 manganese Inorganic materials 0.000 description 2
- 239000011572 manganese Substances 0.000 description 2
- 239000010813 municipal solid waste Substances 0.000 description 2
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 2
- 238000012805 post-processing Methods 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 150000003384 small molecules Chemical class 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- APRRQJCCBSJQOQ-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(N)=CC(S(O)(=O)=O)=CC2=C1 APRRQJCCBSJQOQ-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 229920003043 Cellulose fiber Polymers 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 241000208202 Linaceae Species 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000010612 desalination reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000005360 mashing Methods 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- ZAOCWQZQPKGTRN-UHFFFAOYSA-N nitrous acid;sodium Chemical compound [Na].ON=O ZAOCWQZQPKGTRN-UHFFFAOYSA-N 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000012797 qualification Methods 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- MZSDGDXXBZSFTG-UHFFFAOYSA-M sodium;benzenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC=CC=C1 MZSDGDXXBZSFTG-UHFFFAOYSA-M 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000012192 staining solution Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
- C07C317/48—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Abstract
The present invention relates to a kind of raising dye fixing rates and the intermediate of solubility and preparation method thereof, shown in the structural formula of the reactive dye intermediate such as formula (I):
Description
Technical field
It is especially a kind of suitable for synthesizing digital ink-jet printed or dyeing dyestuff the present invention relates to reactive dyestuff field
Mesosome and preparation method thereof.
Background technique
Digital ink-jet printed technology is a kind of completely new stamp mode, it eliminates Conventional decal mode and needs to make a plate this
Complicated link, can direct spray printing on the fabric, improve the precision of stamp, be truly realized high-quality stamp.It shortens print
Flower process process solves the problems, such as Conventional decal contaminated wastewater, has the advantages that several: 1. total digitalization processing, without making a plate,
Modulate mill base；2. high-quality produces, precision is high, and colour image expressive force is strong；3. clean manufacturing, environmentally friendly.Reactive dye
Ink is most popular a kind of ink in current digital ink-jet printed application field, it is suitable for the fibers such as cotton, fiber crops, flax
Cellulose fiber can be also used on the protein fibres such as wool, silk.Reactive dye be through covalent bond in conjunction with fiber, it
With excellent water-fastness, the performances such as fastness to rubbing.Currently, the digital ink-jet printed reactive dye sold on the market exist
Some applied defects or deficiency, such as: 1. degree of fixation is low, and ink-jet ink must have the characteristic of high colour-fast rate, and fixation is low to be made
At the waste of ink, also can cause environmental pollution；2. insoluble matter is high, the thing of blocking spray head is easy to appear in ink jet process
Therefore spray head can also be damaged；3. compatibility is poor, keep the color of image to gush out uneven, ideal coloured light cannot be reached；
4. frost resistance is poor, because the change of environment temperature is so that ink performance changes, standard of normal use etc. cannot be reached and lacked
It falls into.
Therefore it the object of the present invention is to provide a kind of new dyestuff intermediate, is more suitable for the dyestuff that the intermediate synthesizes
Digital ink-jet printed or dyeing.New dyestuff intermediate introduces carboxyl in contraposition ester molecule, the molten of synthetic dyestuffs both can be improved
Xie Du, and can moderately improve active group (- OSO3H activity), to improve reacting for the reactive dye that thus synthesize and fiber
Speed achievees the purpose that improve degree of fixation.In addition, the introducing of carboxyl, after making its synthetic dyestuffs molecule, easy shape at low ambient temperatures
At supermolecule, so that solubility and dye solution viscosity are improved, and at high temperature, supermolecule is dissociated into small molecule again, thus easily
It spreads dye molecule to fibrous inside, improves dye molecule and fiber molecule collision probability, thus improve degree of fixation.Also
The frost resistance that dye solution can be increased makes it below 0 DEG C without freezing.
Summary of the invention
The technical problem to be solved by the present invention is to develop a kind of dyestuff intermediate, thus the activity dye of intermediate synthesis
Expect that application performance is excellent, strong applicability.The present invention also provides the preparation methods of the dyestuff intermediate.This intermediate is to tie
Be on structure para-ester face position introduce carboxyl, activity between para-ester and sulfonation para-ester, application range is wider.
In order to solve the above-mentioned technical problem, the technical solution adopted by the present invention is that:
A kind of reactive dye intermediate, shown in the structural formula of the reactive dye intermediate such as formula (I):
Name: 2- carboxyl -4- β sulfuryl ethyl sulfuric acid ester group-aniline
Molecular formula: C9H11O8NS2
Molecular weight: 325
The present invention also provides the preparation methods of above-mentioned reactive dye intermediate, include the following steps:
1), chlorosulfonation: 1 part of dry 2- carboxyanilino is added in 6 parts of chlorosulfonic acids, and control temperature exists during charging
50 DEG C or less.After charging, stir evenly；It is warming up to 100 DEG C, is kept for 100-130 DEG C after reaction 6-8 hours, be down to room temperature；
Material is precipitated in ice, obtains pale solid A；
2) it, restores: 1 part of pale solid A is added in the solution dissolved with 1.3 parts of sodium sulfites, used during charging
Liquid alkaline controls pH=7.5-8 and white solid B is obtained by filtration after temperature is kept for 10-50 DEG C, reaction 2 hours；
3), hydroxyethylation: white solid B is dissolved into water and is placed in closed pressure resistant container, epoxy is passed through into solution
Ethane gas, temperature are maintained at 50-80 DEG C, use H2SO4(20%) it adjusts pH=6.8-7.2. to react 10-12 hours, be obtained by filtration
White solid C；
4) it, is esterified: dry white solid C is slowly added into 4 parts of concentrated sulfuric acids, be sufficiently stirred during charging and warm
Control is spent at 40 DEG C hereinafter, being then warming up to 40-45 DEG C, is kept for 4 hours, end of reaction, and ice analyses discharging of saltouing and obtains white admittedly
Body product is target product (I)；
The number is parts by weight.
Preparation principle:
1. chlorosulfonation
2. restoring
3. hydroxyethylation
4. being esterified
Possessed by of the invention the utility model has the advantages that
Dyestuff intermediate of the present invention introduces carboxyl in contraposition ester molecule, the solubility of synthetic dyestuffs not only can be improved, but also can
Appropriateness improves active group (- OSO3H activity) reaches to improve the reaction speed of the reactive dye and fiber that thus synthesize
Improve the purpose of degree of fixation.In addition, the introducing of carboxyl easily forms supermolecule after making its synthetic dyestuffs molecule at low ambient temperatures,
To improve solubility and dye solution viscosity, and at high temperature, supermolecule is dissociated into small molecule again, to easily make dye molecule
It is spread to fibrous inside, improves dye molecule and fiber molecule collision probability, thus improve degree of fixation.Dyestuff can also be increased
The frost resistance of solution makes it below 0 DEG C without freezing.
Specific embodiment
The present invention is further explained in the light of specific embodiments, but the scope of protection of the present invention is not limited.
Embodiment 1
A kind of reactive dye intermediate, shown in the structural formula of the reactive dye intermediate such as formula (I):
The preparation method of the dyestuff intermediate, includes the following steps:
1), chlorosulfonation: 1 part of dry 2- carboxyanilino is slowly added into 6 parts of chlorosulfonic acids, and temperature is controlled during charging
Degree is at 50 DEG C or less.After charging, stir evenly.100 DEG C are to slowly warm up to, after keeping 120-125 DEG C of reaction 8 hours, drop
To room temperature.Material is precipitated in ice, obtains pale solid A.
2) it, restores: 1 part of pale solid A is slowly added into the solution dissolved with 1.3 parts of sodium sulfites, feed process
Middle to control pH=7.5-8 with liquid alkaline, temperature is kept for 25 DEG C.After reaction 2 hours, white solid B is obtained by filtration.
3), hydroxyethylation: white solid B is dissolved into water and is placed in closed pressure resistant container, epoxy is passed through into solution
Ethane gas, temperature are maintained at 60 DEG C, use H2SO4(20%) it adjusts pH=6.8-7.2. to react 12 hours, it is solid that white is obtained by filtration
Body C.
4) it, is esterified: dry white solid C is slowly added into 4 parts of concentrated sulfuric acids, be sufficiently stirred during charging and warm
Degree control is at 40 DEG C or less.Then it is warming up to 40-45 DEG C, is kept for 4 hours.End of reaction, ice analyse discharging of saltouing and obtain white admittedly
Body product is target product (I)；
The number is mass fraction.
Embodiment 2- Application Example
A kind of digital ink-jet dye activity is dark blue, and molecular structural formula is shown in formula (II):
The dark blue preparation method of the digital ink-jet dye activity, includes the following steps:
Step 1, condensation reaction
(1), dissolve
A), bottom water 1800L is added in 5000L reaction kettle, 30~35 DEG C are warming up to, by the 2.4- diamino of 538.5Kg
Benzene sulfonic acid sodium salt is dissolved with water, controls medium 6.5~7.0 with the sodium carbonate liquor of concentration 15%~20%, so that whole materials are complete
Fully dissolved obtains 2.4- diamino benzene sulfonic acid sodium solution, spare.
B), p-aminobenzene sulfonic acid is dissolved according to mass concentration 20%, bottom water 1500L is added in 5000L reaction kettle, risen
P-aminobenzene sulfonic acid 375Kg is added to 35~40 DEG C in temperature, with the sodium carbonate liquor of concentration 15%~20% adjust pH=6.5~
Between 7.0, so that material all dissolves, p-aminobenzene sulfonic acid solution is obtained, it is spare.
(2), primary condensation
A), bottom water 800L, 2500Kg trash ice, Cyanuric Chloride 400Kg are added in 20000L reaction kettle, ice milling aid is added
5Kg, ice time consuming are 15 minutes, and then 2.4- diamino benzene sulfonic acid sodium solution was at the uniform velocity added in 30 minutes used times, during dropwise addition
Temperature is kept for 0~5 DEG C, uses pH=2.5~3.0 of manganese hydrogen sodium regulating solution at any time, and medium is kept to stir 1.5 hours, sampling
Detect reaction end be without extra 2.4- diamino benzene sulfonic acid sodium until, stay a contracting object sample after qualified.
Or addition bottom water 800L, 2500Kg trash ice, Cyanuric Chloride 400Kg, addition ice mill help b), in 20000L reaction kettle
Agent 5Kg, ice time consuming are 15 minutes, and then p-aminobenzene sulfonic acid solution, temperature during dropwise addition was at the uniform velocity added in 30 minutes used times
It is kept for 0~5 DEG C, uses pH=2.5~3.0 of manganese hydrogen sodium regulating solution at any time, keep medium to stir 1.5 hours, sample detection
Reaction end be without extra p-aminobenzene sulfonic acid until, stay a contracting object sample after qualified.
(3), secondary condensation
One contracts after reaction, cooling on the rocks, the 2.4- diamino benzene sulfonic acid sodium solution or p-aminophenyl that will have been dissolved
Sulfonic acid solutions at the uniform velocity carry out two contracting reactions, 5~10 DEG C of temperature are kept after finishing, stirs 3~3.5 hours, takes in one contracting object of addition
Sample is qualification without an extra contracting object with liquid chromatographic detection, obtains two contracting things.
Step 2, diazo-reaction
A), bottom water 3000L is added in 35000L reaction kettle, (the sulfate group vinyl sulfone(RemzaolHuo Xingranliaohuoxingjituan) of 2- amino -5 of 100% amount is added
Base)-benzoic acid 692.7Kg, after mashing 1 hour, addition 510Kg hydrochloric acid is kept for 0~8 DEG C of temperature with ice, rapidly joins nitrous acid
Sodium solution (it is spare to have dissolved sodium nitrite 150Kg) in advance, keeps the aobvious blue of starch potassium iodide paper, pH ﹤ 2 is controlled, in 0~8
DEG C insulation reaction 2~2.5 hours, extra sodium nitrite was removed with sulfamic acid, obtains (the sulfate group vinyl sulfone(RemzaolHuo Xingranliaohuoxingjituan) of 2- amino -5
Base)-benzoic acid diazo liquid.
B), 510Kg hydrochloric acid is added in two contracting things, is kept for 0~8 DEG C of temperature with ice, rapidly joins sodium nitrite solution and (mention
Before to have dissolved sodium nitrite 150Kg spare), keep the aobvious blue of starch potassium iodide paper, pH ﹤ 2 controlled, in 0~8 DEG C of insulation reaction
3.5~4 hours, extra sodium nitrite is removed with sulfamic acid, obtains two contracting things diazo liquid.
Step 3, coupling reaction
The H acid powder of 394Kg is added directly into 2- amino -5 (sulfate group ethylene sulfuryl)-benzoic acid diazo liquid,
With between 15%~20% sodium carbonate liquor of concentration control pH=2.5~3.0, temperature rises to 15~20 DEG C, keeps medium stirring
Reaction 1.5 hours, then medium is adjusted to 3.5~4.0, it stirs 2.5 hours.Acid is even after reaction, obtains acidic coupling object, then two are contracted
Object diazo liquid is added in acidic coupling object, controls pH=6.5~7.0 with sodium carbonate liquor, is kept for 15~20 DEG C of temperature, keeps medium
Between 6.5~7.0, it is stirred to react 2 hours, after reaction sample detection.
Filter to obtain finished product after detection is qualified, can be directly spray-dried, obtain solid powder packaging, as conventional dyes into
Marketing is sold.If as digital ink-jet printed dyestuff, to postprocessing working procedures.
Step 4, post-processing
Stock staining solution after detection is qualified carries out the processes such as desalination, purification with nanometer film, after all technical is qualified, adjusts
Whole dye content 20%~35% can be used as the digital ink-jet printed dyestuff sale of liquid；It is dry with spray drying process, obtain solid powder
End also can be used as the digital ink-jet printed dyestuff sale of solid.
Application performance detection:
Currently, the digital ink-jet reactive navy blue largely used on selling market, molecular structural formula is shown in (III):
It detects and compares with 2 application performance of the embodiment of the present invention:
Detection data report
It is drawn a conclusion by application performance comparison, reactive navy blue prepared by intermediate of the present invention is better than other structures type
Active dark blue dye.
Claims (2)
1. a kind of reactive dye intermediate, it is characterised in that: shown in the structural formula of the reactive dye intermediate such as formula (I):
。
2. the preparation method of reactive dye intermediate described in claim 1, characterized by the following steps:
1), chlorosulfonation: 1 part of dry 2- carboxyanilino is added in 6 parts of chlorosulfonic acids, and control temperature is at 50 DEG C during charging
Below.After charging, stir evenly；It is warming up to 100 DEG C, is kept for 100-130 DEG C after reaction 6-8 hours, be down to room temperature；Ice analysis
Discharging, obtains pale solid A；
2) it, restores: 1 part of pale solid A is added in the solution dissolved with 1.3 parts of sodium sulfites, liquid alkaline is used during charging
It controls pH=7.5-8 and white solid B is obtained by filtration after temperature is kept for 10-50 DEG C, reaction 2 hours；
3), hydroxyethylation: white solid B is dissolved into water and is placed in closed pressure resistant container, ethylene oxide is passed through into solution
Gas, temperature are maintained at 50-80 DEG C, use H2SO4(20%) it adjusts pH=6.8-7.2. to react 10-12 hours, white is obtained by filtration
Solid C；
4) it, is esterified: dry white solid C is slowly added into 4 parts of concentrated sulfuric acids, charging is sufficiently stirred in the process and temperature control
System hereinafter, be then warming up to 40-45 DEG C, is kept for 4 hours, end of reaction at 40 DEG C, and ice analysis discharging of saltouing obtains white solid production
Object is target product (I)；
The number is parts by weight.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
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| Application Number | Priority Date | Filing Date | Title |
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| CN201811259587.2A CN109293539A (en) | 2018-10-26 | 2018-10-26 | A kind of raising dye fixing rate and the intermediate of solubility and preparation method thereof |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109627196A (en) * | 2019-02-18 | 2019-04-16 | 仪征市海帆化工有限公司 | The synthetic method of 2- nitryl-4-thiamphenicol benzoic acid |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3879402A (en) * | 1973-09-26 | 1975-04-22 | Pfizer | Process for preparing 2-chloro-5-sulfamoylbenzoic acids |
| US4346046A (en) * | 1979-07-19 | 1982-08-24 | Sumitomo Chemical Company, Limited | Process for producing aminoaryl-β-sulfatoethylsulfone |
| US4960929A (en) * | 1987-10-17 | 1990-10-02 | Hoechst Aktiengesellschaft | Hydroxyethylsulfonylnitro- and hydroxyethylsulfonylamino-benzoic acids and processes for their preparation |
| CN102433026A (en) * | 2011-09-29 | 2012-05-02 | 天津德凯化工股份有限公司 | Black active dye for pure cotton or cotton and wool blended textile dyeing and preparation method thereof |
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