CN108440994A - A kind of preparation method of active dark blue dye - Google Patents
A kind of preparation method of active dark blue dye Download PDFInfo
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- CN108440994A CN108440994A CN201810453674.5A CN201810453674A CN108440994A CN 108440994 A CN108440994 A CN 108440994A CN 201810453674 A CN201810453674 A CN 201810453674A CN 108440994 A CN108440994 A CN 108440994A
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- blue dye
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- 0 CC([*+])=CC=C(C=*)[N+](C)[N-]C1=C(*)CC(C=C(*)C(CC*=NC2=CC=C(*)CC2*)=C2*)C2=C1* Chemical compound CC([*+])=CC=C(C=*)[N+](C)[N-]C1=C(*)CC(C=C(*)C(CC*=NC2=CC=C(*)CC2*)=C2*)C2=C1* 0.000 description 2
- NXUPOMXBPLNLKL-UHFFFAOYSA-N CC(CC1S(O)(=O)=O)=CC=C1N Chemical compound CC(CC1S(O)(=O)=O)=CC=C1N NXUPOMXBPLNLKL-UHFFFAOYSA-N 0.000 description 1
Classifications
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- 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
- C09B62/503—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring the reactive group being an esterified or non-esterified hydroxyalkyl sulfonyl or mercaptoalkyl sulfonyl group, a quaternised or non-quaternised aminoalkyl sulfonyl group, a heterylmercapto alkyl sulfonyl group, a vinyl sulfonyl or a substituted vinyl sulfonyl group, or a thiophene-dioxide group
- C09B62/507—Azo dyes
- C09B62/513—Disazo or polyazo dyes
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- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a kind of preparation method of active dark blue dye, dye structure general formula is as follows：Wherein, M is hydrogen or alkali metal, and preparation method includes the following steps：1) makeHydrogen chloride and alkali metal nitrites salts react in water, obtain the first reaction mixture；2) it is added into the first reaction mixture in the presence of auxiliary agentReaction, obtains the second reaction mixture；Wherein, auxiliary agent is the composition of naphthalenesulfonate formaldehyde condensation compound and fatty alcohol polyoxyethylene ether；3) make
Description
Technical field
The invention belongs to textile printing and dyeing fields, and in particular to a kind of preparation method of active dark blue dye.
Background technology
Reactive dye, also known as chemically-reactive dyes, for a class of dyes in dyeing with fiber chemically reactive.Reactive dye
As the representative of modern dye industry, faster development is obtained in recent years, at present Reactive Dye for Cellulose Fibre in the world
Annual output accounts for 20% or more of world's dyestuff annual output up to 200,000 tons or more, but as the mankind in terms of environmental protection to wanting
It asks and is increasingly promoted, traditional reactive dye active dark blue dye especially therein, there is such as degree of fixation low, depth is not
Height needs the shortcomings of high-alkali dyeing with high salt, greatly limits the application of reactive dye, therefore develops one group with Gao Gu
The reactive dye that color rate, high dying color, less salt alkali dye are the pursuits of those skilled in the art, wherein the activity of following structures is hidden
Green dyestuff can have preferable coloring：
Wherein, M is hydrogen or alkali metal；
Although the dyestuff of above structure is applied to dyeing, relatively low, purity that there are still yields at present
The shortcomings of relatively low and preparation process sewage yield is big, it is difficult to be applied on a large scale.
Invention content
The technical problem to be solved by the present invention is to overcome the deficiencies of the prior art and provide a kind of system of active dark blue dye
Preparation Method, can be realized under relatively mild reaction condition in high yield, high-purity the advantages that, and preparation process generate sewage
Discharge capacity greatly reduces, and is conducive to the requirement instantly to environmental protection.
In order to solve the above technical problems, the technical solution adopted by the present invention is as follows：
A kind of preparation method of active dark blue dye, the structural formula of the active dark blue dye are：
Wherein, M is hydrogen or alkali metal, and the preparation method includes the following steps：
(1) makeHydrogen chloride and alkali metal nitrites salts react in water, obtain
One reaction mixture；
(2) it is added into first reaction mixture in the presence of auxiliary agentReaction, obtains
Second reaction mixture；Wherein, the auxiliary agent is the composition of naphthalenesulfonate formaldehyde condensation compound and fatty alcohol polyoxyethylene ether；
(3) makeHydrogen chloride and alkali metal nitrites salts react in water, obtain
Third reaction mixture；
(4) second reaction mixture and the third reaction mixture are mixed, the activity is made in reaction
Dark blue dye；
The preparation method also includes selectively step (5)：Acidification step.
In the present invention, being added for hydrogen chloride can be realized by the way that aqueous solution, that is, hydrochloric acid of hydrogen chloride is added.
In the present invention, the alkali metal nitrites salts can be sodium nitrite, potassium nitrite or lithium nitrite etc..
Some preferred aspects according to the present invention, the naphthalenesulfonate formaldehyde condensation compound and the fatty alcohol polyoxyethylene ether
Molar ratio be 1 ︰ 0.6-0.85.
Some preferred aspects according to the present invention, the auxiliary agent with it is describedMolar ratio
For 0.03-0.05:1.
Some preferred aspects according to the present invention in step (1), control the reaction and are carried out at 0~15 DEG C.
Some preferred aspects according to the present invention in step (2), control the reaction and are carried out at 0~10 DEG C.
Some preferred aspects according to the present invention in step (3), control the reaction and are carried out at 0~8 DEG C.
Some preferred aspects according to the present invention in step (4), control the reaction and are carried out at 10~15 DEG C.
Some preferred aspects according to the present invention in step (4), control the reaction and are carried out in the case where pH value is 6-6.5.
Some preferred aspects according to the present invention, the pH value are adjusted by the way that alkali metal hydrogencarbonate is added.According to
Some specific aspects of the present invention, the alkali metal hydrogencarbonate can be sodium bicarbonate, saleratus etc..
Some preferred aspects according to the present invention, it is described in step (1)The chlorine
The molar ratio for changing hydrogen and the alkali metal nitrites salts is 1 ︰ 1-2.5 ︰ 1-1.1.
Some preferred aspects according to the present invention, it is described in step (2)With in step (1)
It is describedMolar ratio be 1 ︰ 0.92-0.98.
Some preferred aspects according to the present invention, it is described in step (3)Chlorine
The molar ratio for changing hydrogen and alkali metal nitrites salts is 1 ︰ 1-2 ︰ 1-1.3.
Some preferred aspects according to the present invention, the preparation method further include post-processing step, the post-processing step
Including：By step (4) or step (5) reaction after reaction solution be filtered, then by gained filtrate be dried processing to get
The solid active dark blue dye.
Due to the use of above technical scheme, the present invention has the following advantages that compared with prior art：
The preparation method of active dark blue dye provided by the invention can realize high receipts under relatively mild reaction condition
The advantages that rate, high-purity, and preparation process generate sewage flow rate greatly reduce, especially meet instantly to environmental protection in terms of
High standards.
Specific implementation mode
Said program is described further below in conjunction with specific embodiment；It should be understood that these embodiments are for illustrating
The basic principles, principal features and advantages of the present invention, and the present invention is not by the scope limitation of following embodiment；It is used in embodiment
Implementation condition further adjustment can be done according to specific requirement, the implementation condition being not specified is usually the item in routine experiment
Part.
In following, unless otherwise specified, all raw materials are both from conventional method system commercially available or by this field
It is standby and obtain.
Embodiment 1
(1) will(361g, 1mol) is added to the water dissolving, keep temperature be 10 ±
2 DEG C, hydrochloric acid solution is added, and (it is the hydrogen chloride content by being calculated to select a concentration of 33% hydrochloric acid solution, molar ratio, is contained
Have hydrogen chloride 75g, 2mol) sodium nitrite solution (containing sodium nitrite 69g, 1mol) is added afterwards, it reacts 3 hours, obtains first
Reaction mixture；
(2) it is added into first mixed solution(293.5g, 0.92mol) and auxiliary agent,
It is stirred to react at 3 ± 2 DEG C 5 hours, obtains the second reaction mixture；Wherein, the auxiliary agent is condensed by naphthalene sulphonate formaldehyde
Object (8.7g creates chemical industry purchased from Shaoxing Zhejiang) and fatty alcohol polyoxyethylene ether (16.6g is purchased from Hai'an petrochemical industry) composition；
(3) will(281g, 1mol) is added in trash ice and water and stirs, and keeps temperature
Degree is 4 ± 1 DEG C, and hydrochloric acid is added, and (it is to contain by the hydrogen chloride being calculated to select a concentration of 33% hydrochloric acid solution, molar ratio
Amount, contains hydrogen chloride 56.3g, 1.5mol) and sodium nitrite (75.9g, 1.1mol), it reacts 3 hours, it is molten to obtain third reaction mixing
Liquid；
(4) second reaction mixture and the third reaction mixture are mixed, sodium bicarbonate is added and adjusts
PH value reacts 4 hours to obtain the 4th reaction mixture to 6.2 ± 0.1 at 12 DEG C；
(5) the 4th reaction mixture is filtered, takes filtrate to be dried to get the active dark blue dye.
Products therefrom structural formula is：
Yield is 92%, purity 95%.
Embodiment 2
(1) will(361g, 1mol) is added to the water dissolving, keep temperature be 12 ±
2 DEG C, hydrochloric acid solution is added, and (it is the hydrogen chloride content by being calculated to select a concentration of 33% hydrochloric acid solution, molar ratio, is contained
Have hydrogen chloride 93.75g, 2.5mol) sodium nitrite solution (containing sodium nitrite 75.9g, 1.1mol) is added afterwards, reaction 2.5 is small
When, obtain the first reaction mixture；
(2) it is added into first mixed solution(303g, 0.95mol) and auxiliary agent, 5
It is stirred to react at ± 2 DEG C 5 hours, obtains the second reaction mixture；Wherein, the auxiliary agent is by naphthalenesulfonate formaldehyde condensation compound
(10.6g creates chemical industry purchased from Shaoxing Zhejiang) and fatty alcohol polyoxyethylene ether (18.8g is purchased from Hai'an petrochemical industry) composition；
(3) will(281g, 1mol) is added in trash ice and water and stirs, and keeps temperature
Degree is 2 ± 1 DEG C, and hydrochloric acid is added, and (it is to contain by the hydrogen chloride being calculated to select a concentration of 33% hydrochloric acid solution, molar ratio
Amount, contains hydrogen chloride 45g, 1.2mol) and sodium nitrite (69g, 1mol), it reacts 2.5 hours, obtains third reaction mixture；
(4) second reaction mixture and the third reaction mixture are mixed, sodium bicarbonate is added and adjusts
PH value reacts 5 hours to obtain the 4th reaction mixture to 6.3 ± 0.1 at 14 ± 1 DEG C；
(5) the 4th reaction mixture is filtered, takes filtrate to be dried to get the active dark blue dye.
Products therefrom structural formula is：
Yield is 91%, purity 94.5%.
Embodiment 3
(1) will(361g, 1mol) is added to the water dissolving, keep temperature be 10 ±
2 DEG C, hydrochloric acid solution is added, and (it is the hydrogen chloride content by being calculated to select a concentration of 33% hydrochloric acid solution, molar ratio, is contained
Have hydrogen chloride 60g, 1.6mol) potassium nitrite solution (containing sodium nitrite 85.1g, 1mol) is added afterwards, it reacts 3 hours, obtains
First reaction mixture；
(2) it is added into first mixed solution(312.6g, 0.98mol) and auxiliary agent,
It is stirred to react at 6 ± 2 DEG C 5 hours, obtains the second reaction mixture；Wherein, the auxiliary agent is condensed by naphthalene sulphonate formaldehyde
Object (10.3g creates chemical industry purchased from Shaoxing Zhejiang) and fatty alcohol polyoxyethylene ether (20.9g is purchased from Hai'an petrochemical industry) composition；
(3) will(281g, 1mol) is added in trash ice and water and stirs, and keeps temperature
Degree is 6 ± 1 DEG C, and hydrochloric acid is added, and (it is to contain by the hydrogen chloride being calculated to select a concentration of 33% hydrochloric acid solution, molar ratio
Amount, contains hydrogen chloride 56.3g, 1.5mol) and potassium nitrite (93.6g, 1.1mol), it reacts 3 hours, it is molten to obtain third reaction mixing
Liquid；
(4) second reaction mixture and the third reaction mixture are mixed, saleratus is added and adjusts
PH value reacts 4 hours to obtain the 4th reaction mixture to 6.1 ± 0.1 at 13 ± 1 DEG C；
(5) the 4th reaction mixture is filtered, takes filtrate to be dried to get the active dark blue dye.
Products therefrom structural formula is：
Yield is 92.5%, purity 96%.
Comparative example 1
Substantially with embodiment 1, difference lies in, not adding assistant in step (2), yield 78%, purity 87%.
Comparative example 2
Substantially with embodiment 1, difference lies in naphthalenesulfonate formaldehyde condensation compound is only added in (2) in step, and yield is
83%, purity 89%.
Comparative example 3
Substantially with embodiment 1, difference lies in fatty alcohol polyoxyethylene ether is only added in (2) in step, and yield is
82.5%, purity 88%.
The above embodiments merely illustrate the technical concept and features of the present invention, and its object is to allow person skilled in the art
Scholar cans understand the content of the present invention and implement it accordingly, and it is not intended to limit the scope of the present invention, all according to the present invention
Equivalent change or modification made by Spirit Essence, should be covered by the protection scope of the present invention.
Claims (10)
1. a kind of preparation method of active dark blue dye, the structural formula of the active dark blue dye are：
Wherein, M is hydrogen or alkali metal, which is characterized in that the preparation method includes the following steps：
(1) makeHydrogen chloride and alkali metal nitrites salts react in water, and it is anti-to obtain first
Answer mixed solution；
(2) it is added into first reaction mixture in the presence of auxiliary agentReaction, obtains second
Reaction mixture；Wherein, the auxiliary agent is the composition of naphthalenesulfonate formaldehyde condensation compound and fatty alcohol polyoxyethylene ether；
(3) makeHydrogen chloride and alkali metal nitrites salts react in water, obtain third
Reaction mixture；
(4) second reaction mixture and the third reaction mixture are mixed, the reactive navy blue is made in reaction
Dyestuff；
The preparation method also includes selectively step (5)：Acidification step.
2. the preparation method of active dark blue dye according to claim 1, which is characterized in that the naphthalene sulphonate formaldehyde contracting
The molar ratio for closing object and the fatty alcohol polyoxyethylene ether is 1:0.6-0.85.
3. the preparation method of active dark blue dye according to claim 1, which is characterized in that the auxiliary agent with it is describedMolar ratio be 0.03-0.05:1.
4. the preparation method of active dark blue dye according to claim 1, which is characterized in that in step (1), described in control
Reaction carries out at 0~15 DEG C；And/or
In step (2), controls the reaction and carried out at 0~10 DEG C；And/or
In step (3), controls the reaction and carried out at 0~8 DEG C；And/or
In step (4), controls the reaction and carried out at 10~15 DEG C.
5. the preparation method of active dark blue dye according to claim 1 or 4, which is characterized in that in step (4), control
The reaction is carried out in the case where pH value is 6-6.5.
6. the preparation method of active dark blue dye according to claim 5, which is characterized in that in step (4), the pH value
It is adjusted by the way that alkali metal hydrogencarbonate is added.
7. the preparation method of active dark blue dye according to claim 1, which is characterized in that described in step (1)The molar ratio of the hydrogen chloride and the alkali metal nitrites salts is 1 ︰ 1-2.5 ︰
1-1.1。
8. the preparation method of active dark blue dye according to claim 1, which is characterized in that described in step (2)With it is described in step (1)Molar ratio be 1 ︰
0.92-0.98。
9. the preparation method of active dark blue dye according to claim 1, which is characterized in that described in step (3)The molar ratio of hydrogen chloride and alkali metal nitrites salts is 1 ︰ 1-2 ︰ 1-1.3.
10. the preparation method of active dark blue dye according to claim 1, which is characterized in that the preparation method is also wrapped
Post-processing step is included, the post-processing step includes：Reaction solution after step (4) or step (5) reaction is filtered, then
Processing is dried to get the solid active dark blue dye in gained filtrate.
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| CN201810453674.5A CN108440994A (en) | 2018-05-14 | 2018-05-14 | A kind of preparation method of active dark blue dye |
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| CN201810453674.5A CN108440994A (en) | 2018-05-14 | 2018-05-14 | A kind of preparation method of active dark blue dye |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112266628A (en) * | 2020-09-27 | 2021-01-26 | 苏州澳缘盛新材料科技有限公司 | Preparation method of reactive dye dark blue |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112266628A (en) * | 2020-09-27 | 2021-01-26 | 苏州澳缘盛新材料科技有限公司 | Preparation method of reactive dye dark blue |
| CN112266628B (en) * | 2020-09-27 | 2022-02-15 | 苏州澳缘盛新材料科技有限公司 | Preparation method of reactive dye dark blue |
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Application publication date: 20180824 |