CN104479403A - Environment-friendly reactive red disazo dye and preparation method thereof - Google Patents
Environment-friendly reactive red disazo dye and preparation method thereof Download PDFInfo
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Abstract
The invention relates to an environment-friendly reactive red disazo dye and a preparation method thereof. The chemical structure general formula is disclosed as Formula (I), wherein X is selected from Na, K or Li; R1 is -H, -CH3(CH2)n-1, -CH3(CH2)n-1O, -COOH or -SO3H; R2 is -CH3(CH2)n-1O; R3 is -(CH2)n-; and n is a whole number, and 1<=n<=4. The disazo dye contains hydroxy, amino and sulfo groups, and thus, is weakly alkaline, thereby being beneficial to lowering the strict preparation conditions and further beneficial to the subsequent dyeing technique. The functional groups are combined with the disazo group to enhance the fixation rate and deep dyeing property.
Description
Technical field
The invention belongs to organic dye field, relate to a kind of disazo dyes, be specifically related to active red disazo dye of a kind of environment-friendly type and preparation method thereof.
Background technology
Reactive dyestuffs, also known as chemically-reactive dyes, for when dyeing and the dye of fiber react with.In this kind of dye molecule containing can with the group of fiber generation chemical reaction, during dyeing, dyestuff and fiber-reactive, form covalent linkage therebetween, becomes overall, and washable and fastness to rubbing is improved.
About the report of red azo dyestuff has a lot in existing patent, such as application number be 201010175509.1 Chinese invention patent disclose a kind of bi-azo active dye, this bi-azo active dye can form purple, redness, the color such as dark blue according to the difference of synthesis material; But be not difficult to find in this patent specification part, its synthesis technique is comparatively harsh, needs to use such as high pressure, nitrogen or hydrogen shield, the conditions such as 90 ~ 100 DEG C, had a strong impact on the possibility of its extensive use.Therefore, synthesize the active orchil of a kind of environment-friendly type, make it have good degree of fixation and depth, and synthesis condition simply just can be applicable to large-scale application.
Summary of the invention
The present invention seeks to provide active red disazo dye of a kind of environment-friendly type and preparation method thereof to overcome the deficiencies in the prior art.
For achieving the above object, the technical solution used in the present invention is: the active red disazo dye of a kind of environment-friendly type, and it is characterized in that, its chemical structure of general formula is such as formula shown in (Ι):
（Ι），
In formula, R
1for-H ,-CH3 (CH2) n-1 ,-CH3 (CH2) n-1O ,-COOX or-SO3X;
X is from Na, K or Li;
R
2for-CH3 (CH2) n-1O;
R
3for-(CH2) n-;
Wherein n is integer and 1≤n≤4.
Optimally, R
1for-CH3CH2 or-SO3X.
Optimally, R
2for-CH3CH2O.
Optimally, R
3for-CH2CH2-.
Optimally, its chemical structure of general formula is such as formula shown in (Ι-1):
（Ι-1），
In formula, X is from Na, K or Li.
Another object of the present invention is to provide the preparation method of the active red disazo dye of a kind of environment-friendly type, comprises the following steps:
A () will
be added to the water dissolving, keeps temperature to be 0 ~ 5 DEG C, adds sodium nitrite solution reaction and obtain the first mixing solutions in 1 ~ 3 hour after adding hydrochloric acid soln, described in
, described hydrochloric acid and described Sodium Nitrite mol ratio be 1:0.5 ~ 0.7:1 ~ 1.1;
B () adds in described first mixing solutions
and anion surfactant, at 5 ~ 10 DEG C, stirring reaction obtains the second mixing solutions in 2 ~ 3 hours, described in
with described
mol ratio be 1:0.96 ~ 0.98, described anion surfactant and described
ratio be 0.5 ~ 1g/mol;
C () will
be added to the water dissolving, keeps temperature to be 0 ~ 5 DEG C, adds sodium nitrite solution reaction and within 1 ~ 3 hour, obtain the 3rd mixing solutions after adding hydrochloric acid soln, described in
, described Sodium Nitrite and described hydrochloric acid mol ratio be 0.90 ~ 0.95:0.90 ~ 0.95:1;
D described 3rd mixing solutions adds in described second mixing solutions by (), add weak base adjust ph to 6 ~ 6.5, and at 10 ~ 15 DEG C, react 1 ~ 3 hour to obtain the 4th mixing solutions, described weak base is sodium bicarbonate, lithium bicarbonate or saleratus;
E () filters described 4th mixing solutions, get filtrate and carry out after film process dry.
Optimally, described step (c) and step (a), step (b) are in no particular order.
Optimally, step (a) is with in step (c), and the feed postition of described hydrochloric acid, described Sodium Nitrite, for dripping, adds speed and is 0.5 ~ 2.5kg/ hour.
Optimally, in described step (a) and step (c), control solution ph and make aobvious blue, the micro-blueness of starch potassium iodide paper of congo-red test paper, when starch potassium iodide paper colour developing is deepened, add a certain amount of described in
or described in
; If when starch potassium iodide paper shows colourless, add a certain amount of described sodium nitrite solution.
Further, step (a), with in step (c), when starch potassium iodide paper shows colourless, is added at a certain amount of described sodium nitrite solution is placed in 5-8 DEG C and is reacted 1 ~ 2 hour, eliminate excessive nitrous acid with a certain amount of thionamic acid.
Because technique scheme is used, the present invention compared with prior art has following advantages: the active red disazo dye of environment-friendly type of the present invention, and its chemical structure of general formula is such as formula shown in (Ι):
(Ι), in formula, X is from Na, K or Li; R
1for-H ,-CH3 (CH2) n-1 ,-CH3 (CH2) n-1O ,-COOH or-SO3H; R
2for-CH3 (CH2) n-1O; R
3for-(CH2) n-; Wherein n is integer and 1≤n≤4, contains hydroxyl, amino and sulfonic group on the one hand, make this dyestuff have weakly alkaline, be conducive to reducing its critical conditions prepared, thus be conducive to follow-up dyeing, be conducive to protection of the environment in disazo dyes; The combination of above-mentioned functional group and tetrazo base, can improve its degree of fixation and depth on the other hand.
Embodiment
The active red disazo dye of environment-friendly type of the present invention, its chemical structure of general formula is such as formula shown in (Ι):
（Ι），
In formula, X is from Na, K or Li; R
1for-H ,-CH3 (CH2) n-1 ,-CH3 (CH2) n-1O ,-COOX or-SO3X; R
2for-CH3 (CH2) n-1O; R
3for-(CH2) n-; Wherein n is integer and 1≤n≤4.Contain the functional groups such as hydroxyl, amino and sulfonic group in disazo dyes on the one hand, effectively can regulate the acid-basicity of disazo dyes, make it keep weakly alkaline; On the other hand tetrazo base can form large π key with phenyl ring, thus can with these functional groups, improve its degree of fixation and depth.Wherein, R
1be preferably-CH3CH2 or-SO3X.R
2be preferably-CH3CH2O.R
3be preferably-CH2CH2-.The chemical structure of general formula of the active red disazo dye of environment-friendly type is preferably such as formula shown in (Ι-1):
（Ι-1），
In formula, X is from Na, K or Li.
The preparation method of the active red disazo dye of above-mentioned environment-friendly type, comprises the following steps:
A () will
be added to the water dissolving, keeps temperature to be 0 ~ 5 DEG C, adds sodium nitrite solution reaction and obtain the first mixing solutions in 1 ~ 3 hour after adding hydrochloric acid soln, described in
, described hydrochloric acid and described Sodium Nitrite mol ratio be 1:0.5 ~ 0.7:1 ~ 1.1; B () adds in described first mixing solutions
and anion surfactant, at 5 ~ 10 DEG C, stirring reaction obtains the second mixing solutions in 2 ~ 3 hours, described in
with described
mol ratio be 1:0.96 ~ 0.98, described anion surfactant and described
ratio be 0.5 ~ 1g/mol; C () will
be added to the water dissolving, keeps temperature to be 0 ~ 5 DEG C, adds sodium nitrite solution reaction and within 1 ~ 3 hour, obtain the 3rd mixing solutions after adding hydrochloric acid soln, described in
, described Sodium Nitrite and described hydrochloric acid mol ratio be 0.90 ~ 0.95:0.90 ~ 0.95:1; D described 3rd mixing solutions adds in described second mixing solutions by (), add weak base adjust ph to 6 ~ 6.5, and at 10 ~ 15 DEG C, react 1 ~ 3 hour to obtain the 4th mixing solutions, described weak base is sodium bicarbonate, lithium bicarbonate or saleratus; It should be noted that the 3rd mixing solutions and the 4th mixing solutions are guarantee in mixing
with
mol ratio be 1:1; E () filters described 4th mixing solutions, get filtrate and carry out after film process dry.Preparation method's reaction conditions of the active red disazo dye of environment-friendly type of the present invention is simple, does not need the reaction conditionss such as protection of inert gas, high temperature, vacuum, high pressure, is conducive to its scale operation; And take filtrate after reaction, filter residue can directly be collected, and filtrate is dry after only needing to carry out film process, and side reaction degree is little, pollutes little, is conducive to protection of the environment.
Step (c) and step (a), step (b) in no particular order, experimentally specifically can carry out reasonable arrangement.Step (a) is with in step (c), the feed postition of described hydrochloric acid, described Sodium Nitrite is for dripping, and adding speed is 0.5 ~ 2.5kg/ hour, because azo reaction is comparatively violent, therefore need to reduce its reaction severe degree, thus the generation of by product can be reduced.In described step (a) and step (c), control solution ph and make aobvious blue, the micro-blueness of starch potassium iodide paper of congo-red test paper, when starch potassium iodide paper colour developing is deepened, add a certain amount of described in
or described in
; If when starch potassium iodide paper shows colourless, add a certain amount of described sodium nitrite solution; Effectively can improve the utilization ratio of reaction product like this, reduce the consumption of reaction product, cost-saving and improve the productive rate of dyestuff.Step (a), with in step (c), when starch potassium iodide paper shows colourless, is added at a certain amount of described sodium nitrite solution is placed in 5 ~ 8 DEG C and is reacted 1 ~ 2 hour, eliminate excessive nitrous acid, prevent nitrous acid contaminate environment with a certain amount of thionamic acid.
Below will the present invention is described in detail by specific embodiment.
Embodiment 1
The present embodiment provides a kind of environment-friendly type active red disazo dye, and its chemical structural formula is shown below:
；
The preparation method of the active red disazo dye of above-mentioned environment-friendly type is as follows:
A () will
be added to the water dissolving, adds ice cube and make water temperature be 0 DEG C, adds sodium nitrite solution and react and obtain the first mixing solutions in 1 hour after adding hydrochloric acid soln,
, hydrochloric acid and Sodium Nitrite mol ratio be 1:0.5:1, the feed postition of hydrochloric acid, Sodium Nitrite is for dripping, and adding speed is 0.5kg/ hour; Control solution ph and make aobvious blue, the micro-blueness of starch potassium iodide paper of congo-red test paper, when starch potassium iodide paper colour developing is deepened, add a certain amount of
; If when starch potassium iodide paper shows colourless, add the sodium nitrite solution of a certain amount of (inventory added is determined according to the change of test paper color) here, react 2 hours at being placed in 5 DEG C, eliminate excessive nitrous acid with the thionamic acid of corresponding amount;
B () adds in above-mentioned first mixing solutions
and sodium metnylene bis-naphthalene sulfonate, at 5 DEG C, stirring reaction obtains the second mixing solutions in 3 hours,
with
mol ratio be 1:0.96, sodium metnylene bis-naphthalene sulfonate (anion surfactant) with
ratio be 0.5g/mol;
C () will
be added to the water dissolving, adds ice cube and make water temperature be 0 DEG C, adds sodium nitrite solution and react and within 1 hour, obtain the 3rd mixing solutions after adding hydrochloric acid soln,
, Sodium Nitrite and hydrochloric acid mol ratio be 0.90:0.90:1; It should be noted that
with
mol ratio be 1:1; Control solution ph and make aobvious blue, the micro-blueness of starch potassium iodide paper of congo-red test paper, when starch potassium iodide paper colour developing is deepened, add a certain amount of
; If when starch potassium iodide paper shows colourless, add the sodium nitrite solution of a certain amount of (inventory added is determined according to the change of test paper color) here, react 2 hours at being placed in 5 DEG C, eliminate excessive nitrous acid with the thionamic acid of corresponding amount;
D 3rd mixing solutions adds in the second mixing solutions by (), add sodium bicarbonate adjust ph to 6, at 10 DEG C, react 3 hours to obtain the 4th mixing solutions,
E () filters described 4th mixing solutions, get filtrate carry out film process be placed on 85 DEG C at vacuum-drying.
Embodiment 2
The present embodiment provides consistent, more inconsistent unlike its temperature of reaction, reaction times and material ratio, specific as follows with embodiment 1 of the active red disazo dye of a kind of environment-friendly type:
A () will
be added to the water dissolving, keeps water temperature to be 5 DEG C, adds sodium nitrite solution and react and obtain the first mixing solutions in 3 hours after adding hydrochloric acid soln,
, hydrochloric acid and Sodium Nitrite mol ratio be 1:0.7:1.1, the feed postition of hydrochloric acid, Sodium Nitrite is for dripping, and adding speed is 2.5kg/ hour; Control solution ph and make aobvious blue, the micro-blueness of starch potassium iodide paper of congo-red test paper, when starch potassium iodide paper colour developing is deepened, add a certain amount of
; If when starch potassium iodide paper shows colourless, add the sodium nitrite solution of a certain amount of (inventory added is determined according to the change of test paper color) here, react 1 hour at being placed in 8 DEG C, eliminate excessive nitrous acid with the thionamic acid of corresponding amount;
B () adds in above-mentioned first mixing solutions
and sodium laurylsulfonate, at 10 DEG C, stirring reaction obtains the second mixing solutions in 2 hours,
with
mol ratio be 1:0.98, sodium laurylsulfonate (anion surfactant) with
ratio be 1g/mol;
C () will
be added to the water dissolving, makes water temperature remain 5 DEG C, adds sodium nitrite solution and react and within 3 hours, obtain the 3rd mixing solutions after adding hydrochloric acid soln,
, Sodium Nitrite and hydrochloric acid mol ratio be 0.95:0.95:1; It should be noted that
with
mol ratio be 1:1; Control solution ph and make aobvious blue, the micro-blueness of starch potassium iodide paper of congo-red test paper, when starch potassium iodide paper colour developing is deepened, add a certain amount of
; If when starch potassium iodide paper shows colourless, add the sodium nitrite solution of a certain amount of (inventory added is determined according to the change of test paper color) here, react 1 hour at being placed in 8 DEG C, eliminate excessive nitrous acid with the thionamic acid of corresponding amount;
D 3rd mixing solutions adds in the second mixing solutions by (), add sodium bicarbonate adjust ph to 6.5, at 15 DEG C, react 1 hour to obtain the 4th mixing solutions,
E () filters described 4th mixing solutions, get filtrate carry out film process be placed on 100 DEG C at vacuum-drying.
Embodiment 3
The present embodiment provides consistent, more inconsistent unlike its temperature of reaction, reaction times and material ratio, specific as follows with embodiment 1 of the active red disazo dye of a kind of environment-friendly type:
A () will
be added to the water dissolving, keeps water temperature to be 3 DEG C, adds sodium nitrite solution and react and obtain the first mixing solutions in 2 hours after adding hydrochloric acid soln,
, hydrochloric acid and Sodium Nitrite mol ratio be 1:0.6:1.05, the feed postition of hydrochloric acid, Sodium Nitrite is for dripping, and adding speed is 2kg/ hour; Control solution ph and make aobvious blue, the micro-blueness of starch potassium iodide paper of congo-red test paper, when starch potassium iodide paper colour developing is deepened, add a certain amount of
; If when starch potassium iodide paper shows colourless, add the sodium nitrite solution of a certain amount of (inventory added is determined according to the change of test paper color) here, react 1.5 hours at being placed in 6 DEG C, eliminate excessive nitrous acid with the thionamic acid of corresponding amount;
B () adds in above-mentioned first mixing solutions
and sodium cetanesulfonate, at 8 DEG C, stirring reaction obtains the second mixing solutions in 2.5 hours,
with
mol ratio be 1:0.97, sodium cetanesulfonate (anion surfactant) with
ratio be 0.8g/mol;
C () will
be added to the water dissolving, makes water temperature remain 3 DEG C, adds sodium nitrite solution and react and within 2 hours, obtain the 3rd mixing solutions after adding hydrochloric acid soln,
, Sodium Nitrite and hydrochloric acid mol ratio be 0.93:0.93:1; It should be noted that
with
mol ratio be 1:1; Control solution ph and make aobvious blue, the micro-blueness of starch potassium iodide paper of congo-red test paper, when starch potassium iodide paper colour developing is deepened, add a certain amount of
; If when starch potassium iodide paper shows colourless, add the sodium nitrite solution of a certain amount of (inventory added is determined according to the change of test paper color) here, react 1.5 hours at being placed in 6 DEG C, eliminate excessive nitrous acid with the thionamic acid of corresponding amount;
D 3rd mixing solutions adds in the second mixing solutions by (), add sodium bicarbonate adjust ph to 6.2, at 12 DEG C, react 2 hours to obtain the 4th mixing solutions,
E () filters described 4th mixing solutions, get filtrate carry out film process be placed on 90 DEG C at vacuum-drying.
Embodiment 4
The present embodiment provides a kind of environment-friendly type active red disazo dye, and its chemical structural formula is shown below:
（Ι），
In formula, R
1for-CH3CH2; X is K; R
2for-CH3CH2O; R
3for-CH2CH2-.
Embodiment 5
The present embodiment provides a kind of environment-friendly type active red disazo dye, and its chemical structural formula is shown below:
(Ι),
In formula, R
1for-COONa, X are Na, R
2for-CH3O, R
3for-CH2-.
Embodiment 6
The present embodiment provides a kind of environment-friendly type active red disazo dye, and its chemical structural formula is shown below:
（Ι），
In formula, X is Li, R
1for-CH3 (CH2) 3, R
2for-CH3 (CH2) 3O, R
3for-(CH2) 4-.
Embodiment 7
The present embodiment provides a kind of environment-friendly type active red disazo dye, and its chemical structural formula is shown below:
（Ι），
In formula, X is Na, R
1for-SO3Na, R
2for-CH3CH2 O, R
3for-(CH2) 2-.
Above-described embodiment is only for illustrating technical conceive of the present invention and feature; its object is to person skilled in the art can be understood content of the present invention and implement according to this; can not limit the scope of the invention with this; all equivalences done according to spirit of the present invention change or modify, and all should be encompassed within protection scope of the present invention.
Claims (10)
1. the active red disazo dye of environment-friendly type, it is characterized in that, its chemical structure of general formula is such as formula shown in (Ι):
（Ι），
In formula, R
1for-H ,-CH3 (CH2) n-1 ,-CH3 (CH2) n-1O ,-COOX or-SO3X;
X is Na, K or Li;
R
2for-CH3 (CH2) n-1O;
R
3for-(CH2) n-;
Wherein n is integer and 1≤n≤4.
2. the active red disazo dye of environment-friendly type according to claim 1, is characterized in that: R
1for-CH3CH2 or-SO3X.
3. the active red disazo dye of environment-friendly type according to claim 1, is characterized in that: R
2for-CH3CH2O.
4. the active red disazo dye of environment-friendly type according to claim 1, is characterized in that: R
3for-CH2CH2-.
5. the active red disazo dye of environment-friendly type according to claim 1, is characterized in that: its chemical structure of general formula is such as formula shown in (Ι-1):
（Ι-1），
In formula, X is from Na, K or Li.
6. the preparation method of the active red disazo dye of arbitrary described environment-friendly type in claim 1 to 5, is characterized in that, comprise the following steps:
A () will
be added to the water dissolving, keeps temperature to be 0 ~ 5 DEG C, adds sodium nitrite solution reaction and obtain the first mixing solutions in 1 ~ 3 hour after adding hydrochloric acid soln, described in
, described hydrochloric acid and described Sodium Nitrite mol ratio be 1:0.5 ~ 0.7:1 ~ 1.1;
B () adds in described first mixing solutions
and anion surfactant, at 5 ~ 10 DEG C, stirring reaction obtains the second mixing solutions in 2 ~ 3 hours, described in
with described
mol ratio be 1:0.96 ~ 0.98, described anion surfactant and described
ratio be 0.5 ~ 1g/mol;
C () will
be added to the water dissolving, keeps temperature to be 0 ~ 5 DEG C, adds sodium nitrite solution reaction and within 1 ~ 3 hour, obtain the 3rd mixing solutions after adding hydrochloric acid soln, described in
, described Sodium Nitrite and described hydrochloric acid mol ratio be 0.90 ~ 0.95:0.90 ~ 0.95:1;
D described 3rd mixing solutions adds in described second mixing solutions by (), add weak base adjust ph to 6 ~ 6.5, and at 10 ~ 15 DEG C, react 1 ~ 3 hour to obtain the 4th mixing solutions, described weak base is sodium bicarbonate, lithium bicarbonate or saleratus;
E () filters described 4th mixing solutions, get filtrate and carry out after film process dry.
7. the preparation method of the active red disazo dye of environment-friendly type according to claim 6, is characterized in that: described step (c) and step (a), step (b) are in no particular order.
8. the preparation method of the active red disazo dye of environment-friendly type according to claim 6, is characterized in that: in step (a) and step (c), the feed postition of described hydrochloric acid, described Sodium Nitrite, for dripping, adds speed and is 0.5 ~ 2.5kg/ hour.
9. the preparation method of the active red disazo dye of environment-friendly type according to claim 6, it is characterized in that: described step (a) is with in step (c), control solution ph and make aobvious blue, the micro-blueness of starch potassium iodide paper of congo-red test paper, when starch potassium iodide paper colour developing deepen time, add a certain amount of described in
or described in
; If when starch potassium iodide paper shows colourless, add a certain amount of described sodium nitrite solution.
10. the preparation method of the active red disazo dye of environment-friendly type according to claim 9, it is characterized in that: step (a) is with in step (c), when starch potassium iodide paper shows colourless, add at a certain amount of described sodium nitrite solution is placed in 5-8 DEG C and react 1 ~ 2 hour, eliminate excessive nitrous acid with a certain amount of thionamic acid.
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Cited By (1)
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| CN111057397A (en) * | 2019-12-31 | 2020-04-24 | 浙江科永化工有限公司 | Reactive red dye composition, dye product and application thereof |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111057397A (en) * | 2019-12-31 | 2020-04-24 | 浙江科永化工有限公司 | Reactive red dye composition, dye product and application thereof |
| CN111057397B (en) * | 2019-12-31 | 2021-08-24 | 浙江科永化工有限公司 | Reactive red dye composition, dye product and application thereof |
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