CN106065199A - A kind of active orange being applicable to low temperature dyeing and preparation method thereof - Google Patents
A kind of active orange being applicable to low temperature dyeing and preparation method thereof Download PDFInfo
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- CN106065199A CN106065199A CN201610391752.4A CN201610391752A CN106065199A CN 106065199 A CN106065199 A CN 106065199A CN 201610391752 A CN201610391752 A CN 201610391752A CN 106065199 A CN106065199 A CN 106065199A
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- acid
- orange
- aniline
- dyeing
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- 238000004043 dyeing Methods 0.000 title claims abstract description 38
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- 230000000694 effects Effects 0.000 claims abstract description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 41
- 238000006243 chemical reaction Methods 0.000 claims description 38
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 32
- 238000006277 sulfonation reaction Methods 0.000 claims description 29
- 239000012954 diazonium Substances 0.000 claims description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 claims description 27
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 21
- KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 claims description 17
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 16
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 16
- HBZVNWNSRNTWPS-UHFFFAOYSA-N 6-amino-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(O)C2=CC(N)=CC=C21 HBZVNWNSRNTWPS-UHFFFAOYSA-N 0.000 claims description 14
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 14
- -1 aniline 2,5-disulfonic acid Diazonium compound Chemical class 0.000 claims description 14
- 239000000843 powder Substances 0.000 claims description 14
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 14
- 238000003756 stirring Methods 0.000 claims description 14
- 239000007864 aqueous solution Substances 0.000 claims description 13
- 239000000975 dye Substances 0.000 claims description 13
- SQYUJKVKVFILNB-UHFFFAOYSA-N methyl 2-amino-4-[(2,5-dichlorophenyl)carbamoyl]benzoate Chemical compound C1=C(N)C(C(=O)OC)=CC=C1C(=O)NC1=CC(Cl)=CC=C1Cl SQYUJKVKVFILNB-UHFFFAOYSA-N 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 10
- 235000010288 sodium nitrite Nutrition 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 229920000742 Cotton Polymers 0.000 claims description 4
- 229920002678 cellulose Polymers 0.000 claims description 4
- 239000001913 cellulose Substances 0.000 claims description 4
- 150000001989 diazonium salts Chemical class 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- 238000010009 beating Methods 0.000 claims description 2
- 238000005352 clarification Methods 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 2
- INOIOAWTVPHTCJ-UHFFFAOYSA-N 6-acetamido-4-hydroxy-3-[[4-(2-sulfooxyethylsulfonyl)phenyl]diazenyl]naphthalene-2-sulfonic acid Chemical compound CC(=O)NC1=CC=C2C=C(C(N=NC3=CC=C(C=C3)S(=O)(=O)CCOS(O)(=O)=O)=C(O)C2=C1)S(O)(=O)=O INOIOAWTVPHTCJ-UHFFFAOYSA-N 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 230000009257 reactivity Effects 0.000 abstract description 5
- 238000005265 energy consumption Methods 0.000 abstract description 3
- 239000000243 solution Substances 0.000 description 19
- 230000008878 coupling Effects 0.000 description 12
- 238000010168 coupling process Methods 0.000 description 12
- 238000005859 coupling reaction Methods 0.000 description 12
- 229910052708 sodium Inorganic materials 0.000 description 11
- 239000011734 sodium Substances 0.000 description 11
- 239000011435 rock Substances 0.000 description 10
- 238000001816 cooling Methods 0.000 description 5
- 238000001514 detection method Methods 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- 238000001694 spray drying Methods 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000007599 discharging Methods 0.000 description 3
- 230000002708 enhancing effect Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 238000003912 environmental pollution Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000002351 wastewater Substances 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 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000010018 discharge printing Methods 0.000 description 1
- 239000003344 environmental pollutant Substances 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 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
- C09B33/00—Disazo and polyazo dyes of the types A->K<-B, A->B->K<-C, or the like, prepared by diazotising and coupling
- C09B33/02—Disazo dyes
- C09B33/08—Disazo dyes in which the coupling component is a hydroxy-amino compound
- C09B33/10—Disazo dyes in which the coupling component is a hydroxy-amino compound in which the coupling component is an amino naphthol
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/38—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using reactive dyes
- D06P1/384—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using reactive dyes reactive group not directly attached to heterocyclic group
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/58—Material containing hydroxyl groups
- D06P3/60—Natural or regenerated cellulose
- D06P3/66—Natural or regenerated cellulose using reactive dyes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/82—Textiles which contain different kinds of fibres
- D06P3/8204—Textiles which contain different kinds of fibres fibres of different chemical nature
- D06P3/8219—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing hydroxyl and amide groups
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring (AREA)
Abstract
The invention discloses a kind of active orange being applicable to low temperature dyeing and preparation method thereof.The structural formula of this activity orange is as shown in Equation 1:In formula 1 formula 1, R1And R2One of them be NH2, another is H.The active orange of the present invention can be applicable to low temperature dyeing (about 40 DEG C), and reactivity worth is stable, good level-dyeing property, and tinctorial yield is high, easily cleans, and reduces energy consumption.
Description
Technical field
The invention belongs to Dyestuff synthesis field, be specifically related to a kind of active orange being applicable to low temperature dyeing and system thereof
Preparation Method.
Background technology
Environmental pollution and protection have become as society significant problem, and dye industry is then faced with baptism, society
The step that can advance can not stop, and enterprise wants length in the new situation and inspires exhibition, and product quality must reach a new height.
Existing dyestuff, synthesis technique is complicated, and produces all multi-pollutants, is thrown in environment and pollutes.And, mesh
The dyestuff of front routine, its dyeing temperature is at 60-70 DEG C, to reach higher tinctorial yield and degree of fixation.Dyeing temperature height will necessarily
Increase the energy consumption of dyeing.
Summary of the invention
In order to reduce environmental pollution, response national energy-saving reduces discharging policy, and the active orange in the present invention is broken the normal procedure
Utilizing lower temperature to dye, more stable compared with traditional handicraft product reactivity worth, production cost is cheaper, solves traditional orange work
Property the problems such as dyestuff level-dyeing property is poor, residual liquid is many, have that production cost is low, reactivity worth is stable, good level-dyeing property, degree of fixation high, molten
The advantages such as Xie Du is good, and quantity of wastewater effluent is few.
The active orange being applicable to low temperature dyeing of the present invention, it is adaptable to low temperature dyeing, reactivity worth is stable, level dyeing
Property is good, and light fastness 5 grades, fastness to wet rubbing reach 4 grades, and degree of fixation reaches more than 87%, and enhancing rate is up to 10%, dyeing residual liquid
Few, belong to low temperature environment-friendly energy-saving dyestuff, meet national energy-saving and reduce discharging policy.This product is except for traditional cellulose
Beyond stock-dye, it is more suitable for continuous knot dyeing, discharge printing and brocade/cotton one-bath dyeing.
The present invention provide the active orange being applicable to low temperature dyeing, structural formula as shown in Equation 1:
Formula 1
In formula 1, R1And R2One of them be-NH2, another is H.
The present invention also provides for the preparation method of above-mentioned active orange, comprises the steps:
1) by aniline 2,5-disulfonic acid carries out diazo-reaction with hydrochloric acid and sodium nitrite in aqueous solution, obtains aniline 2,5-disulfonic acid
Diazonium compound；
2) J acid or γ-acid mix with water, and after making beating is dissolved, regulation pH value is 6 ~ 7.5, standby after clarification；
3) aniline 2 that step 1) obtains, 5-disulfonic acid diazonium compound and step 2) J acid that obtains or γ-acid aqueous solution carry out instead
A deserved conjugates；
4) sulfonation para-ester carries out diazo-reaction with hydrochloric acid and sodium nitrite in aqueous solution, obtains sulfonation para-ester diazonium thing；
5) conjugates that the sulfonation para-ester diazonium thing addition step 3) that step 4) obtains obtains carries out reaction and obtains two
Secondary conjugates, filters, is drying to obtain.
Preferably, step 1) is aniline 2, adds hydrochloric acid, be cooled to 0-3 DEG C, add nitrous after stirring in 5-disulfonic acid
Acid sodium aqueous solution, 3-7 DEG C of reaction, obtains aniline 2,5-disulfonic acid diazonium compound.
Preferably, step 2) in regulate pH value for 6 ~ 7.5 with sodium hydroxide or sodium bicarbonate.
Preferably, step 3) is the aniline 2 step 1) obtained, and 5-disulfonic acid diazonium compound joins step 2) obtain
J acid or γ-acid aqueous solution in, control temperature 0-3 DEG C, with sodium bicarbonate dry powder adjust pH=3 ~ 4, carry out reacting to obtain a coupling
Thing.
Preferably, step 4) is that sulfonation para-ester adds in hydrochloric acid after stirring, is cooled to 0-5 DEG C, adds sodium nitrite
Aqueous solution, 3-7 DEG C of reaction, obtains sulfonation para-ester diazonium thing.
Preferably, step 5) is that sulfonation para-ester diazonium thing step 4) obtained adds the coupling that step 3) obtains
In thing, adjust pH=6.5 ~ 7.5 with sodium bicarbonate dry powder, control temperature 10-15 DEG C, reaction, obtain secondary conjugates, filter, be dried i.e.
?.
Preferably, aniline 2,5-disulfonic acid: J acid or γ-acid: mass ratio=250 of sulfonation para-ester ~ 260:234 ~ 241:
360~380。
The present invention also provides for the application of the above-mentioned active orange being applicable to low temperature dyeing, described activity orange
For cellulose dyeing, continuous knot dyeing, discharge, stamp and brocade/cotton One Bath Dyeing Process.
Preferably, the dyeing temperature of described activity orange is 35 ~ 45 DEG C.
The present invention is applicable to the active orange of low temperature dyeing and has the following characteristics that
1) production technology cleaning, environmental protection: using after synthesis and be spray-dried, quantity of wastewater effluent is few.
2) low temperature dyeing (about 40 DEG C), reactivity worth is stable, good level-dyeing property, and tinctorial yield is high, easily cleans, and reduces energy consumption.
3) dissolubility is high, containing multiple sulfonic acid groups in this dye structure, can be widely used in cellulose dyeing,
Continuous knot dyeing and discharge, resisting printing.
4) the cotton One Bath Dyeing Process of brocade it is adapted to.
5) enhancing rate is good: enhancing rate reaches 10%.
6) degree of fixation is high: this dye fixing rate is up to 87%, and low temperature dyeing residual liquid is few, can alleviate dyeing environmental protection pressure
Power, meets national energy-saving and reduces discharging policy.
Detailed description of the invention
Further explaining the present invention below by some preferred embodiments, these embodiments are only to the present invention
Explain rather than protection scope of the present invention is formed any restriction.
Dyestuff preparation method below embodiment 1-5 of the present invention, raw material used in these embodiments is on market common
Industrial chemicals.
Raw material number in following example each means mass fraction.
Embodiment 1
1) aniline 2,5-disulfonic acid diazonium: at 251 parts of aniline 2,5-disulfonic acid adds 54 parts of hydrochloric acid (in terms of hydrogen chloride) stirrings 3
On the rocks after hour lower the temperature in 0-3 DEG C, add 72 parts of sub-sodium (being made into the aqueous solution that mass percent concentration is 30% to use),
3-7 DEG C maintains reaction to obtain aniline 2,5-disulfonic acid diazonium compound in 4 hours；
2) J acid dissolves: be added to the water by 236 parts of J acid, pulls an oar when 15-20 DEG C 1 hour and dissolves, then adjusts with sodium hydroxide solution
PH value is 6.5；
3) coupling: aniline 2,5-disulfonic acid diazonium compound joins in J acid solution, controls temperature 0-3 DEG C, and reaction 4 is little
Time, adjust pH=3.5 with sodium bicarbonate dry powder, after reaction completely, obtain a conjugates；
4) secondary diazonium: 361 parts of sulfonation para-ester add on the rocks after 43 parts of hydrochloric acid stir 2 hours cooling in 0-5 DEG C, add 69
The sub-sodium (being made into 30% solution) of part, maintains reaction to obtain sulfonation para-ester diazonium thing in 3 hours at 3-7 DEG C；；
5) secondary coupling: sulfonation para-ester diazonium thing is added in a conjugates, adjust pH=7.0 with sodium bicarbonate dry powder, control temperature
Spending 10-15 DEG C, carry out reacting 6 hours, with profit circle method detection terminal, terminal is to obtaining secondary conjugates, to it after reaction completely
Filtering and carry out spray drying again and pack to obtain product (1), it has a following structure:
(1)
Being computed, yield is 97%, and purity is 88%.
Embodiment 2
1) aniline 2,5-disulfonic acid diazonium: at 251 parts of aniline 2,5-disulfonic acid adds 54 parts of hydrochloric acid (in terms of hydrogen chloride) stirrings 3
On the rocks after hour lower the temperature in 0-3 DEG C, add 72 parts of sub-sodium (being made into 30% solution), 3-7 DEG C maintain reaction 4 hours aniline
2,5-disulfonic acid diazonium compounds；
2) γ-acid dissolves: be added to the water by 236 parts of γ-acid, pulls an oar when 15-20 DEG C 1 hour and dissolves, then uses sodium hydroxide solution
Adjusting pH value is 6.5；
3) coupling: aniline 2,5-disulfonic acid diazonium compound joins in γ-acid solution, controls temperature 0-3 DEG C, and reaction 4 is little
Time, adjust pH=3.5 with sodium bicarbonate dry powder, after reaction completely, obtain a conjugates；
4) secondary diazonium: 361 parts of sulfonation para-ester add on the rocks after 43 parts of hydrochloric acid stir 2 hours cooling in 0-5 DEG C, add 69
The sub-sodium (being made into 30% solution) of part, maintains reaction to obtain sulfonation para-ester diazonium thing in 3 hours at 3-7 DEG C；
5) secondary coupling: sulfonation para-ester diazonium thing is added in a conjugates, adjust pH=7.0 with sodium bicarbonate dry powder, control temperature
Spending 10-15 DEG C, carry out reacting 6 hours, with profit circle method detection terminal, terminal is to obtaining secondary conjugates, to it after reaction completely
Filtering and carry out spray drying again and pack to obtain product (2), it has a following structure:
(2)
Being computed, yield is 97%, and purity is 85%.
Embodiment 3
1) aniline 2,5-disulfonic acid diazonium: at 253 parts of aniline 2,5-disulfonic acid adds 55 parts of hydrochloric acid (in terms of hydrogen chloride) stirrings 2
On the rocks after hour lower the temperature in 0-3 DEG C, add 70 parts of sub-sodium (being made into 30% solution), 3-7 DEG C maintain reaction 3 hours aniline
2,5-disulfonic acid diazonium compounds；
2) γ-acid dissolves: be added to the water by 239 parts of γ-acid, pulls an oar when 15-20 DEG C 1 hour and dissolves, then uses sodium hydroxide solution
Adjusting pH value is 7.0；
3) coupling: aniline 2,5-disulfonic acid diazonium compound joins in γ-acid solution, controls temperature 0-3 DEG C, and reaction 5 is little
Time, adjust pH=4.0 with sodium bicarbonate dry powder, after reaction completely, obtain a conjugates；
4) secondary diazonium: 365 parts of sulfonation para-ester add on the rocks after 43 parts of hydrochloric acid stir 2 hours cooling in 0-5 DEG C, add 69
The sub-sodium (being made into 30% solution) of part, maintains reaction to obtain sulfonation para-ester diazonium thing in 4 hours at 3-7 DEG C；
5) secondary coupling: sulfonation para-ester diazonium thing is added in a conjugates, adjust pH=7.2 with sodium bicarbonate dry powder, control temperature
Spending 10-15 DEG C, carry out reacting 7 hours, with profit circle method detection terminal, terminal is to obtaining secondary conjugates, to it after reaction completely
Filtration carries out spray drying again and packs to obtain product (2).
Being computed, yield is 95%, and purity is 83%.
Embodiment 4
1) aniline 2,5-disulfonic acid diazonium: at 253 parts of aniline 2,5-disulfonic acid adds 55 parts of hydrochloric acid (in terms of hydrogen chloride) stirrings 2
On the rocks after hour lower the temperature in 0-3 DEG C, add 70 parts of sub-sodium (being made into 30% solution), 3-7 DEG C maintain reaction 3 hours aniline
2,5-disulfonic acid diazonium compounds；
2) J acid dissolves: be added to the water by 239 parts of J acid, pulls an oar when 15-20 DEG C 1 hour and dissolves, then adjusts with sodium hydroxide solution
PH value is 7.0；
3) coupling: aniline 2,5-disulfonic acid diazonium compound joins in J acid solution, controls temperature 0-3 DEG C, and reaction 5 is little
Time, adjust pH=4.0 with sodium bicarbonate dry powder, after reaction completely, obtain a conjugates；
4) secondary diazonium: 365 parts of sulfonation para-ester add on the rocks after 43 parts of hydrochloric acid stir 2 hours cooling in 0-5 DEG C, add 69
The sub-sodium (being made into 30% solution) of part, maintains reaction to obtain sulfonation para-ester diazonium thing in 4 hours at 3-7 DEG C；
5) secondary coupling: sulfonation para-ester diazonium thing is added in a conjugates, adjust pH=7.2 with sodium bicarbonate dry powder, control temperature
Spending 10-15 DEG C, carry out reacting 7 hours, with profit circle method detection terminal, terminal is to obtaining secondary conjugates, to it after reaction completely
Filtration carries out spray drying again and packs to obtain product (1).
Being computed, yield is 96%, and purity is 86%.
Embodiment 5
1) aniline 2,5-disulfonic acid diazonium: at 260 parts of aniline 2,5-disulfonic acid adds 55 parts of hydrochloric acid (in terms of hydrogen chloride) stirrings 2
On the rocks after hour lower the temperature in 0-3 DEG C, add 73 parts of sub-sodium (being made into 30% solution), 3-7 DEG C maintain reaction 3 hours aniline
2,5-disulfonic acid diazonium compounds；
2) J acid dissolves: be added to the water by 241 parts of J acid, pulls an oar when 15-20 DEG C 1 hour and dissolves, then adjusts with sodium hydroxide solution
PH value is 7.0；
3) coupling: aniline 2,5-disulfonic acid diazonium compound joins in J acid solution, controls temperature 0-3 DEG C, and reaction 4 is little
Time, adjust pH=4.0 with sodium bicarbonate dry powder, after reaction completely, obtain a conjugates；
4) secondary diazonium: 380 parts of sulfonation para-ester add on the rocks after 45 parts of hydrochloric acid stir 2 hours cooling in 0-5 DEG C, add 73
The sub-sodium (being made into 30% solution) of part, maintains reaction to obtain sulfonation para-ester diazonium thing in 4 hours at 3-7 DEG C；
5) secondary coupling: sulfonation para-ester diazonium thing is added in a conjugates, adjust pH=7.0 with sodium bicarbonate dry powder, control temperature
Spending 10-15 DEG C, carry out reacting 8 hours, with profit circle method detection terminal, terminal is to obtaining secondary conjugates, to it after reaction completely
Filtration carries out spray drying again and packs to obtain product (1).
Being computed, yield is 98%, and purity is 90%.
Following table is the main application indexes of dyestuff of the present invention (at a temperature of 40 DEG C, carry out dyeing):
Embodiment described above is only the preferred embodiment lifted by absolutely proving the present invention, and protection scope of the present invention is not
It is limited to this.The equivalent that those skilled in the art are made on the basis of the present invention substitutes or conversion, all the guarantor of the present invention
Within the scope of protecting.Protection scope of the present invention is as the criterion with claims.
Claims (10)
1. the active orange being applicable to low temperature dyeing, it is characterised in that structural formula as shown in Equation 1:
Formula 1
In formula 1, R1And R2One of them be-NH2, another is H.
2. the preparation method of the active orange described in claim 1, it is characterised in that comprise the steps:
1) by aniline 2,5-disulfonic acid carries out diazo-reaction with hydrochloric acid and sodium nitrite in aqueous solution, obtains aniline 2,5-disulfonic acid
Diazonium compound；
2) J acid or γ-acid mix with water, and after making beating is dissolved, regulation pH value is 6 ~ 7.5, standby after clarification；
3) aniline 2 that step 1) obtains, 5-disulfonic acid diazonium compound and step 2) J acid that obtains or γ-acid aqueous solution carry out instead
A deserved conjugates；
4) sulfonation para-ester carries out diazo-reaction with hydrochloric acid and sodium nitrite in aqueous solution, obtains sulfonation para-ester diazonium thing；
5) conjugates that the sulfonation para-ester diazonium thing addition step 3) that step 4) obtains obtains carries out reaction and obtains two
Secondary conjugates, filters, is drying to obtain.
The preparation method of activity orange the most according to claim 2, it is characterised in that step 1) is aniline 2, and 5-is double
Sulfonic acid adds hydrochloric acid, is cooled to 0-3 DEG C after stirring, adds sodium nitrite in aqueous solution, 3-7 DEG C of reaction, obtain aniline 2,
5-disulfonic acid diazonium compound.
The most according to claim 2 activity orange preparation method, it is characterised in that step 2) in sodium hydroxide
Or sodium bicarbonate regulation pH value is 6 ~ 7.5.
The preparation method of activity orange the most according to claim 2, it is characterised in that step 3) is for obtain step 1)
The aniline 2 arrived, 5-disulfonic acid diazonium compound joins step 2) in the J acid that obtains or γ-acid aqueous solution, control temperature 0-3
DEG C, to adjust pH=3 ~ 4 with sodium bicarbonate dry powder, carry out reacting to obtain a conjugates.
The preparation method of activity orange the most according to claim 2, it is characterised in that step 4) is sulfonation para-ester
Add after hydrochloric acid stirs, be cooled to 0-5 DEG C, add sodium nitrite in aqueous solution, 3-7 DEG C of reaction, obtain sulfonation para-ester weight
Nitrogen thing.
The preparation method of activity orange the most according to claim 2, it is characterised in that step 5) is for obtain step 4)
To sulfonation para-ester diazonium thing add in a conjugates obtaining of step 3), adjust pH=6.5 ~ 7.5, control with sodium bicarbonate dry powder
Temperature 10-15 DEG C processed, reaction, obtain secondary conjugates, filter, be drying to obtain.
8., according to the preparation method of the active orange described in any one of claim 2 ~ 7, it is characterised in that aniline 2,5-is double
Sulfonic acid: J acid or γ-acid: mass ratio=250 of sulfonation para-ester ~ 260:234 ~ 241:360 ~ 380.
9. the application of the active orange being applicable to low temperature dyeing described in claim 1, it is characterised in that described reactive orange
Color dyestuff is for cellulose dyeing, continuous knot dyeing, discharge, stamp and brocade/cotton One Bath Dyeing Process.
Application the most according to claim 9, it is characterised in that the dyeing temperature of described activity orange is 35 ~ 45
℃。
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| US4069218A (en) * | 1974-04-10 | 1978-01-17 | Ciba-Geigy Corporation | Water-soluble fiber-reactive disazo dyestuffs |
| CN101117449A (en) * | 2007-09-04 | 2008-02-06 | 大连理工大学 | A high-concentration composite reactive dye |
| CN101671487A (en) * | 2009-08-18 | 2010-03-17 | 天津德凯化工股份有限公司 | Method for synthesizing red reactive dye |
| CN102898868A (en) * | 2012-10-31 | 2013-01-30 | 无锡润新染料有限公司 | Reactive orange dye and preparation method thereof |
| CN103554989A (en) * | 2013-10-24 | 2014-02-05 | 浙江亿得化工有限公司 | Low-temperature composite activated black dye and application thereof |
-
2016
- 2016-06-06 CN CN201610391752.4A patent/CN106065199B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4069218A (en) * | 1974-04-10 | 1978-01-17 | Ciba-Geigy Corporation | Water-soluble fiber-reactive disazo dyestuffs |
| CN101117449A (en) * | 2007-09-04 | 2008-02-06 | 大连理工大学 | A high-concentration composite reactive dye |
| CN101671487A (en) * | 2009-08-18 | 2010-03-17 | 天津德凯化工股份有限公司 | Method for synthesizing red reactive dye |
| CN102898868A (en) * | 2012-10-31 | 2013-01-30 | 无锡润新染料有限公司 | Reactive orange dye and preparation method thereof |
| CN103554989A (en) * | 2013-10-24 | 2014-02-05 | 浙江亿得化工有限公司 | Low-temperature composite activated black dye and application thereof |
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