CN104927396B - A kind of composite reactive crimson and its preparation method and application - Google Patents
A kind of composite reactive crimson and its preparation method and application Download PDFInfo
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- CN104927396B CN104927396B CN201510294125.4A CN201510294125A CN104927396B CN 104927396 B CN104927396 B CN 104927396B CN 201510294125 A CN201510294125 A CN 201510294125A CN 104927396 B CN104927396 B CN 104927396B
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Abstract
The invention discloses a kind of composite reactive crimson and its preparation method and application, the dyestuff is counted in parts by weight, including 30~80 parts of formulas (1) compound, 10~30 parts of formula (2) compounds and 10~40 parts of formula (3) compounds, wherein, R1For H, OCH3Or SO3H；M is alkali metal ion.The composite reactive crimson has that stability is good, enhancing rate is good, solubility is high, degree of fixation is high, synchronism is good for dyeing, good level-dyeing property, color reproducibility are good, the premium properties such as especially prominent higher light fastness and prominent pile-on properties and resistance to oxygen bleaching, suitable for dyeing and printing of cellulosic fibre materials, especially suitable for cotton, cotton/wash.
Description
Technical field
The present invention relates to reactive dyestuff field, and in particular to a kind of composite reactive crimson and preparation method thereof and should
With.
Background technology
Reactive dye chromatogram is wide, lovely luster, excellent performance, strong applicability, its form and aspect and performance substantially with market pair
The requirement of fiber and dress material is adapted, and is one of cellulose dyeing and the most important dyestuff of stamp, and originally some are with insoluble
Property azo, vulcanization and reducing dye dyeing textile also gradually adopt reactive dyeing.In addition, reactive dye are in protein
Fiber, synthetic fibers and some tencels such as soybean, milk protein fiber on application also constantly expand.
The shortcomings that reactive dye are unique is hydrolysis problem, and influences one of an important factor for cotton fiber degree of fixation improves.
Usual dyestuff set on cotton in the basic conditions, and this basicity promotes the reaction of dyestuff and water, causes its inactivation.Inactivation
Dyestuff, namely hydrolised dye, it is impossible to reacted with cotton, so as to cause considerable part dyestuff to be depleted.Hydrolised dye and base
Physical adherence occurs for matter, is removed until the washing process stage, thus causes washing fastness problem.
In addition, light fastness and resistance to oxygen bleaching performance also need further to improve after the textile dyeing such as reactive dye progress cotton, and
And the dark kind even more rareness of sulfur dye and reducing dye etc. can be substituted in reactive dyestuff field.
The content of the invention
It is an object of the invention to provide a kind of new composite reactive crimson, the high light fastness of the dyestuff, and good consolidates
The dyeing of the multiple fiber cellulose fibers such as color ability and splendid depth, the cotton that is particularly suitable for use in, cotton/wash.
Composite reactive crimson provided by the invention, is counted in parts by weight, including 30~80 parts formula (1) compound,
10~30 parts of formula (2) compounds and 10~40 parts of formula (3) compounds：
Wherein, R1For-H ,-OCH3Or-SO3H；M is alkali metal ion.In alkali metal ion it is more conventional have sodium ion,
Potassium ion etc..
There is a chloro-s-triazine base and ethene sulfuryl double-active radical in above three component, their affinity to fiber,
Dye-uptake, degree of fixation, level-dyeing property, enhancing rate, to electrolyte salt, to color fixing agent bases, to dyeing temperature susceptibility and wash
Net rate is all more close, and the above-mentioned active deep red dyestuff compounded out has that stability is good, solubility is high, degree of fixation is high, dyeing is same
The good, good level-dyeing property of step property, color reproducibility are good, especially prominent higher light fastness and prominent pile-on properties and resistance to oxygen bleaching etc.
Premium properties, suitable for dyeing and printing of cellulosic fibre materials.
Preferably, in above-mentioned composite reactive crimson, M is sodium ion.
The present invention also provides a kind of preparation method of above-mentioned composite reactive crimson Chinese style (1) compound, and step includes：
1. H acid is beaten, pH=7.0 is adjusted to dissolving with liquid caustic soda, is added in Cyanuric Chloride mashing liquid and is once contracted
Reaction is closed, adjusts pH=3.5~4.0, is reacted 2 hours；
2. N- ethyl meta esters are added in said mixture solution, be warming up to T=40 DEG C, maintain pH=3.5~
4.0, reaction obtains two contracting liquid in 4 hours；
3. adding water and ice to be beaten 30 minutes orthanilic acid and hydrochloric acid mixed solution, it is 30% to add mass percentage concentration
Sodium nitrite in aqueous solution, maintain T=0-5 DEG C of temperature, unnecessary natrium nitrosum eliminated with sulfamic acid after reaction 1 hour；When
It is aobvious colourless using starch potassium iodide paper detection, while terminal when showing blue is detected with Congored test paper and is reached, obtain diazo liquid；
4. diazo liquid is added in two contracting liquid, pH=7.0~7.5 are adjusted, maintain temperature T=8~15 DEG C, it is small to react 6
When after terminal reach, obtain coupling solution；Coupling solution is filtered to remove into insoluble matter to carry out being spray-dried the formula of producing (1) compound.
The present invention also provides a kind of preparation method of above-mentioned composite reactive crimson Chinese style (2) compound, and step includes：
1. H acid is beaten, pH=7.0 is adjusted to dissolving with liquid caustic soda, is added in Cyanuric Chloride mashing liquid and is once contracted
Reaction is closed, adjusts pH=3.5~4.0, is reacted 2 hours；
2. N- ethyl meta esters are added in said mixture solution, be warming up to T=40 DEG C, maintain pH=3.5~
4.0, reaction obtains two contracting liquid in 4 hours；
3. water and ice is added to be beaten 30 points para-ester, O-methoxy para-ester or the mixed liquor of sulfonation para-ester and hydrochloric acid
Clock, the sodium nitrite in aqueous solution that mass percentage concentration is 30% is added, maintain temperature T=0~5 DEG C, reaction uses amino after 1 hour
Sulfonic acid eliminates unnecessary natrium nitrosum；When aobvious colourless using starch potassium iodide paper detection while aobvious with Congored test paper detection
Terminal reaches when blue, obtains diazo liquid；
4. above-mentioned diazo liquid is added in two contracting liquid, pH=7.0~7.5 are adjusted, maintain temperature T=8~15 DEG C, reaction
Terminal reaches after 6 hours, obtains coupling solution；Coupling solution is filtered to remove into insoluble matter to carry out being spray-dried the formula of producing (2) compound.
The present invention also provides a kind of preparation method of above-mentioned composite reactive crimson Chinese style (3) compound, and step includes：
1. adding water and ice to be beaten 30 minutes the mixed liquor of para-ester and hydrochloric acid, the Asia that mass percentage concentration is 30% is added
Sodium nitrate aqueous solution, temperature T=0~5 DEG C are maintained to eliminate unnecessary natrium nitrosum with sulfamic acid after reacting 1 hour；Work as use
Starch potassium iodide paper detection is aobvious colourless, while terminal when showing blue is detected with Congored test paper and is reached, and obtains para-ester diazo liquid；
2. J acid is beaten, pH=7.0 is adjusted to dissolving with liquid caustic soda, is added in para-ester diazo liquid and is once coupled
Reaction, adjusts pH=2.0~3.0, maintenance reaction 4 hours, and once coupling finishes；
3. conjugates are adjusted into pH=7.0~7.5 with sodium bicarbonate dry powder, temperature T=10~15 DEG C, reaction 4 are maintained
Terminal reaches after~5 hours, obtains secondary coupling solution；Secondary coupling solution is filtered to remove insoluble matter, carries out being spray-dried the formula of producing
(3) compound.
In above-mentioned multiple preparation methods, the chemical name of described H acid is 1- amino-8-naphthol -3,6- disulfonic acid, and J is sour
Chemical name be 2- amino -5- naphthols -7- sulfonic acid.
The present invention also provides a kind of dark red dye composition, including any one above-mentioned present invention also provide it is a kind of compound
Active deep red dyestuff.
Preferably, in above-mentioned dark red dye composition, in addition to one kind in accelerant, color fixing agent and softening agent or
It is several.
Preferably, in above-mentioned dark red dye composition, the accelerant is Na2SO4Or NaCl, the color fixing agent are
NaOH、Na2CO3Or NaHCO3。
Preferably, in above-mentioned dark red dye composition, in addition to fire retardant and/or electrostatic agent.
The present invention also provides dark red dye composition the answering in cellulosic fibre material printing and dyeing described in any of the above
With.
Compared with prior art, the invention has the advantages that：
The composite reactive crimson of the present invention, formed by developing three kinds of dyestuffs of compounding meticulously, three components therein
In there is a chloro-s-triazine base and ethene sulfuryl double-active radical, it has high response, high enhancing rate, high-dissolvability, high fixation
Rate, especially there are the premium properties such as good depth, high light fastness, resistance to oxygen bleaching, beautiful in colour, dyeing residual liquid is few, belongs to ring
Protect energy saving dyestuff.Their affinity, dye-uptake, degree of fixation, level-dyeing property, enhancing rates to fiber, to electrolyte salt, to solid
Toner bases is all more close to dyeing temperature susceptibility and clean rate.The dyestuff has that stability is good, enhancing rate is good, molten
Solution degree is high, degree of fixation is high, dyeing synchronism is good, good level-dyeing property, color reproducibility are good, especially prominent higher light fastness and prominent
The premium properties such as the pile-on properties gone out and resistance to oxygen bleaching, suitable for dyeing and printing of cellulosic fibre materials, especially suitable for cotton, cotton/wash.
Embodiment
With reference to specific embodiment, the invention will be further described, so that those skilled in the art can be more preferable
Understand the present invention and can be practiced, but illustrated embodiment is not as a limitation of the invention.
First, prepared by compound
Formula (1 ') preparation method is as follows：
1. H acid is beaten, pH=7.0 is adjusted to dissolving with liquid caustic soda, is added in Cyanuric Chloride mashing liquid and is once contracted
Close reaction, adjust pH=3.5~4.0, reaction 2 hours it is stand-by.
2. N- ethyl meta esters are added in said mixture solution, be warming up to T=40 DEG C, maintain pH=3.5~
4.0, reaction obtains two contracting liquid in 4 hours.
3. adding water, ice to be beaten 30 minutes orthanilic acid, hydrochloric acid, 30% (mass percentage concentration) natrium nitrosum is added
The aqueous solution, maintains temperature T=0~5 DEG C, and reaction eliminates unnecessary natrium nitrosum with sulfamic acid after 1 hour.Work as starch potassium iodide
Test paper shows colourless, and Congored test paper shows blue terminal and reached, and obtains diazo liquid.
4. above-mentioned diazo liquid is added in two contracting liquid, pH=7.0~7.5 are adjusted, maintain temperature T=8~15 DEG C, reaction
Terminal reaches after 6 hours, obtains coupling solution.Coupling solution is filtered to remove into insoluble matter to carry out being spray-dried the formula of producing (1 ') dyestuff.
Formula (2 ') preparation method is as follows：
1. H acid is beaten, pH=7.0 is adjusted to dissolving with liquid caustic soda, is added in Cyanuric Chloride mashing liquid and is once contracted
Close reaction, adjust pH=3.5~4.0, reaction 2 hours it is stand-by.
2. N- ethyl meta esters are added in said mixture solution, be warming up to T=40 DEG C, maintain pH=3.5~
4.0, reaction obtains two contracting liquid in 4 hours.
3. adding water, ice to be beaten 30 minutes para-ester (O-methoxy para-ester or sulfonation para-ester), hydrochloric acid, 30% is added
(mass percentage concentration) sodium nitrite in aqueous solution, temperature T=0~5 DEG C are maintained, it is unnecessary that reaction is eliminated after 1 hour with sulfamic acid
Natrium nitrosum.When starch potassium iodide paper shows colourless, Congored test paper shows blue terminal and reached, and obtains diazo liquid.
4. above-mentioned diazo liquid is added in two contracting liquid, pH=7.0~7.5 are adjusted, maintain temperature T=8~15 DEG C, reaction
Terminal reaches after 6 hours, obtains coupling solution.Coupling solution is filtered to remove into insoluble matter to carry out being spray-dried the formula of producing (2 ') dyestuff.
Wherein, step 3. it is middle using para-ester when obtain product (2 ' -1), step 3. it is middle using O-methoxy para-ester when obtain
Product (2 ' -2), step 3. it is middle using sulfonation para-ester when obtain product (2 ' -3).
Formula (3 ') preparation method is as follows：
1. adding water, ice to be beaten 30 minutes para-ester, hydrochloric acid, it is water-soluble to add 30% (mass percentage concentration) natrium nitrosum
Liquid, temperature T=0~5 DEG C are maintained to eliminate unnecessary natrium nitrosum with sulfamic acid after reacting 1 hour.Work as starch potassium iodide paper
Aobvious colourless, Congored test paper shows blue terminal and reached, and obtains diazo liquid.
2. J acid is beaten, pH=7.0 is adjusted to dissolving with liquid caustic soda, is added in para-ester diazol and is once coupled
Reaction, adjusts pH=2.0~3.0, maintenance reaction 4 hours, and once coupling finishes.
3. conjugates are adjusted into pH=7.0~7.5 with sodium bicarbonate dry powder, temperature T=10~15 DEG C are maintained, react 4-
Terminal reaches after 5 hours, obtains secondary coupling solution.Secondary coupling solution is filtered to remove insoluble matter, carries out being spray-dried the formula of producing
(3 ') dyestuff.
2nd, composite reactive crimson is prepared and applied
Embodiment 1：
By 55g meeting formulas (1 ') dyestuff, 20g meeting formulas (2 ') dyestuff (2 ' -1) and 25g meeting formulas (3 ') dyestuff through abundant
Ground mechanical mixture and obtain the present invention composite reactive crimson, this dyestuff cellulosic fibre material can be dyeing into Exposure to Sunlight jail
Degree is high, the peony of deep, the resistance to oxygen bleaching function admirable of color.
Embodiment 2：
The aqueous solution of 55g formulas (1 '), the aqueous solution containing 20g formulas (2 ') dyestuff (2 ' -1) will be contained and contain 25g formulas
Stir drying after the aqueous solution mixing of (3 ') dyestuff, obtains the composite reactive crimson of the present invention, this dyestuff can be by fibre
Cellulose fiber material is dyeing into the peony of deep, the resistance to oxygen bleaching function admirable of light fastness height, color.
Embodiment 3：
By 70g meeting formulas (1 ') dyestuff, 15g meeting formulas (2 ') dyestuff (2 ' -2) and 15g meeting formulas (3 ') dyestuff through abundant
Ground mechanical mixture and obtain the present invention composite reactive crimson, this dyestuff cellulosic fibre material can be dyeing into Exposure to Sunlight jail
Degree is high, the peony of deep, the resistance to oxygen bleaching function admirable of color.
Embodiment 4：
The aqueous solution of 80g meeting formulas (1 ') dyestuff, the aqueous solution of 10g meeting formulas (2 ') dyestuff (2 ' -2) and 10g are met
The aqueous solution of formula (3 ') dyestuff obtains the composite reactive crimson of the present invention through fully mechanical mixture, and this dyestuff can be by fibre
Cellulose fiber material is dyeing into the peony of deep, the resistance to oxygen bleaching function admirable of light fastness height, color.
Embodiment 5：
By 80g meeting formulas (1 ') dyestuff, 10g meeting formulas (2 ') dyestuff (2 ' -3) and 10g meeting formulas (3 ') dyestuff through abundant
Ground mechanical mixture and obtain the present invention composite reactive crimson, this dyestuff cellulosic fibre material can be dyeing into Exposure to Sunlight jail
Degree is high, the peony of deep, the resistance to oxygen bleaching function admirable of color.
Embodiment 6：
By 60g meeting formulas (1 ') dyestuff, 20g meeting formulas (2 ') dyestuff (2 ' -3) and 20g meeting formulas (3 ') dyestuff through abundant
Ground mechanical mixture and obtain the present invention composite reactive crimson, this dyestuff cellulosic fibre material can be dyeing into Exposure to Sunlight jail
Degree is high, the peony of deep, the resistance to oxygen bleaching function admirable of color.
Following examples are the application of dyestuff of the present invention：
Embodiment 7 dyes：
First it is set fully to dissolve with appropriate water 4g composite reactive crimsons as made from embodiment 1, then constant volume
In 500mL volumetric flasks.Draw 10mL dye liquors mixed with 50mL water, then addition 4g cottons, 1.8g sodium sulphate, then with 1 DEG C/
The programming rate of minute is raised to 60 DEG C, and 1g sodium carbonate is added after being kept for 30 minutes, then is kept for 60 DEG C dye 30 minutes, then taking-up
By dye cotton, seethed with excitement soap boiling 15 minutes with non-ionic cleaning agent, carry out cold water, after hot water intersects cleaning, and at 70 DEG C or so
Drying, it obtains staining power height, good level-dyeing property, favorable reproducibility, thick in color and the good peony of gorgeous, resistance to oxygen bleaching.
Embodiment 8 dyes：
First it is set fully to dissolve with appropriate water 4g composite reactive crimsons as made from embodiment 2, then constant volume
In 500mL volumetric flasks.Draw 10mL dye liquors mixed with 50mL water, then addition 4g cottons, 1.8g sodium sulphate, then with 1 DEG C/
The programming rate of minute is raised to 60 DEG C, and 1g sodium carbonate is added after being kept for 30 minutes, then is kept for 60 DEG C dye 30 minutes, then taking-up
By dye cotton, seethed with excitement soap boiling 15 minutes with non-ionic cleaning agent, carry out cold water, after hot water intersects cleaning, and at 70 DEG C or so
Drying, it is good that it obtains few staining power height, good level-dyeing property, favorable reproducibility, dyeing residual liquid, thick in color and gorgeous, resistance to oxygen bleaching
Peony.
Embodiment 9 dyes：
First it is set fully to dissolve with appropriate water 4g composite reactive crimsons as made from embodiment 3, then constant volume
In 500mL volumetric flasks.Draw 10mL dye liquors mixed with 50mL water, then addition 4g cottons, 1.8g sodium sulphate, then with 1 DEG C/
The programming rate of minute is raised to 60 DEG C, and 1g sodium carbonate is added after being kept for 30 minutes, then is kept for 60 DEG C dye 30 minutes, then taking-up
By dye cotton, seethed with excitement soap boiling 15 minutes with non-ionic cleaning agent, carry out cold water, after hot water intersects cleaning, and at 70 DEG C or so
Drying, it is good that it obtains few staining power height, good level-dyeing property, favorable reproducibility, dyeing residual liquid, thick in color and gorgeous, resistance to oxygen bleaching
Peony.
Embodiment 10 dyes：
First it is set fully to dissolve with appropriate water 4g composite reactive crimsons as made from embodiment 4, then constant volume
In 500mL volumetric flasks.Draw 10mL dye liquors mixed with 50mL water, then addition 4g cottons, 1.8g sodium sulphate, then with 1 DEG C/
The programming rate of minute is raised to 60 DEG C, and 1g sodium carbonate is added after being kept for 30 minutes, then is kept for 60 DEG C dye 30 minutes, then taking-up
By dye cotton, seethed with excitement soap boiling 15 minutes with non-ionic cleaning agent, carry out cold water, after hot water intersects cleaning, and at 70 DEG C or so
Drying, it is good that it obtains few staining power height, good level-dyeing property, favorable reproducibility, dyeing residual liquid, thick in color and gorgeous, resistance to oxygen bleaching
Peony.
Embodiment 11 dyes：
First it is set fully to dissolve with appropriate water 4g composite reactive crimsons as made from embodiment 5, then constant volume
In 500mL volumetric flasks.Draw 10mL dye liquors mixed with 50mL water, then addition 4g cottons, 1.8g sodium sulphate, then with 1 DEG C/
The programming rate of minute is raised to 60 DEG C, and 1g sodium carbonate is added after being kept for 30 minutes, then is kept for 60 DEG C dye 30 minutes, then taking-up
By dye cotton, seethed with excitement soap boiling 15 minutes with non-ionic cleaning agent, carry out cold water, after hot water intersects cleaning, and at 70 DEG C or so
Drying, it is good that it obtains few staining power height, good level-dyeing property, favorable reproducibility, dyeing residual liquid, thick in color and gorgeous, resistance to oxygen bleaching
Peony.
Embodiment 12 dyes：
First it is set fully to dissolve with appropriate water 4g composite reactive crimsons as made from embodiment 6, then constant volume
In 500mL volumetric flasks.Draw 10mL dye liquors mixed with 50mL water, then addition 4g cottons, 1.8g sodium sulphate, then with 1 DEG C/
The programming rate of minute is raised to 60 DEG C, and 1g sodium carbonate is added after being kept for 30 minutes, then is kept for 60 DEG C dye 30 minutes, then taking-up
By dye cotton, seethed with excitement soap boiling 15 minutes with non-ionic cleaning agent, carry out cold water, after hot water intersects cleaning, and at 70 DEG C or so
Drying, it is good that it obtains few staining power height, good level-dyeing property, favorable reproducibility, dyeing residual liquid, thick in color and gorgeous, resistance to oxygen bleaching
Peony.
Following table is that 1~6 dark red dye composition of embodiment contrasts with active red 3BS applications Indexs measure：
Embodiment described above is only to absolutely prove preferred embodiment that is of the invention and being lifted, protection model of the invention
Enclose not limited to this.The equivalent substitute or conversion that those skilled in the art are made on the basis of the present invention, in the present invention
Protection domain within.Protection scope of the present invention is defined by claims.
Claims (7)
- A kind of 1. composite reactive crimson, it is characterised in that count in parts by weight, including 30~80 parts formula (1) compound, 10~30 parts of formula (2) compounds and 10~40 parts of formula (3) compounds：Wherein, R1For-H ,-OCH3Or-SO3H；M is alkali metal ion.
- 2. composite reactive crimson according to claim 1, it is characterised in that M is sodium ion.
- 3. a kind of dark red dye composition, it is characterised in that including the composite reactive crimson described in claim 1 or 2.
- 4. dark red dye composition according to claim 3, it is characterised in that also including accelerant, color fixing agent and soft One or more in soft dose.
- 5. dark red dye composition according to claim 4, it is characterised in that the accelerant is Na2SO4Or NaCl, The color fixing agent is NaOH, Na2CO3Or NaHCO3。
- 6. the dark red dye composition according to claim 4 or 5, it is characterised in that also including fire retardant and/or electrostatic Agent.
- 7. application of any described dark red dye composition of claim 3~6 in cellulosic fibre material printing and dyeing.
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| CN108192384B (en) * | 2018-02-12 | 2019-05-14 | 泰兴锦云染料有限公司 | A kind of red reactive dye mixture and its application |
| CN108641408A (en) * | 2018-05-25 | 2018-10-12 | 吴江桃源染料有限公司 | A kind of composite reactive scarlet dye and its application |
| CN111019390B (en) * | 2019-12-26 | 2021-02-02 | 浙江劲光实业股份有限公司 | Preparation method of composite active bright red dye |
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| CN101250333A (en) * | 2008-04-08 | 2008-08-27 | 赵卫国 | Reactive deep red RGB diazo dyes and preparation method thereof |
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