CN108165049A - A kind of digit printing active liquid dyestuff and preparation method thereof - Google Patents
A kind of digit printing active liquid dyestuff and preparation method thereof Download PDFInfo
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- CN108165049A CN108165049A CN201810137479.1A CN201810137479A CN108165049A CN 108165049 A CN108165049 A CN 108165049A CN 201810137479 A CN201810137479 A CN 201810137479A CN 108165049 A CN108165049 A CN 108165049A
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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
-
- 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
- C09B62/51—Monoazo 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
- 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
- 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
- D06P1/44—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 insoluble pigments or auxiliary substances, e.g. binders
- D06P1/673—Inorganic compounds
- D06P1/67333—Salts or hydroxides
- D06P1/6735—Salts or hydroxides of alkaline or alkaline-earth metals with anions different from those provided for in D06P1/67341
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- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Coloring (AREA)
Abstract
The present invention relates to a kind of digit printing active liquid dyestuff, it is characterized in that it contains useful the following general formula（1）The reactive dye of expression：Wherein D is the aromatic compound that benzene or naphthalene frenulum have sulfuric acid ester ethyl sulfone；Li+ x.Na+ yX and y is number more than zero in ion pair, and x:The ratio of y is 1:5~5:1.The invention further relates to the preparation methods of the digit printing active liquid dyestuff.The present invention has the advantages that good storage stability and stablizes in storing process unhydrolyzed.
Description
Technical field
The present invention relates to a kind of active liquid dyestuffs more particularly to a kind of digit printing active liquid dyestuff and preparation method thereof.
Background technology
Digit printing is the product of modern science and technology application that this kind of adjoint computer technology is continued to develop and generated, relatively
There are many advantages using flexible and changeable, operation intelligence, production safety environmental protection etc. with traditional printing and dyeing.Current digital
In stamp field, active ink is using a kind of relatively more extensive ink, can be applied to cellulose fibre, protein fibre etc. and knits
On object, including fabrics such as cotton, artificial silk, flax, silks, it can assign polyamide fibre PRINTED FABRIC excellent washing fastness, it can also
Instead of chrome dye for woolen dyed, and with to the increasingly strict of production environment pollution and safety problem, active ink by
Gradually replace reduction, mordant dye etc. and further expand application range.
The active ink of digit printing has the application adaptability of reactive dye higher requirement, a function admirable
Reactive dye need to have and have relatively low salt content, excellent dye uptake, higher solubility and stability of solution；Huntsman
Company also discloses that a series of reactive dye mixture of Vinyl-Sulfone Types in patent WO2004/069937, which mixes
Closing object has the characteristics that high activity, good color yield, excellent detergency and wet fastness.
The characteristics of however, as reactive dye itself, easily hydrolyzes, band in water with the active group of fibration mostly
Carry out stable storage sex chromosome mosaicism.For the reactive dye of Vinyl-Sulfone Type, a large amount of beta-hydroxyethyl sulfuryl sulphur is contained in dye structure
Acid group can hydrolyze when storage, generate hydrogen sulfate ion, the pH value of ink be caused constantly to decline, while dyestuff
The solubility of itself declines.So the problem of active ink maximum is to solve the problems, such as dyestuff storage stability and solubility.It is logical
Desalination is crossed to improve the solubility of dyestuff and reduction salt content and by adding in auxiliary agent（Buffer）To adjust dyestuff in solution
In stability of equilibrium, be usual technological means in the industry at present.Desalting technology can significantly reduce the salt content of dyestuff really,
And the solubility of dyestuff is improved to a certain extent；Though right system buffer, which can play, alleviates the hydrolysis of reactive dye in water,
The balance of dye solution system is temporarily maintained, but can not completely inhibit or eliminate the progress of hydrolysis, with storage time
Extension, dyestuff hydrolysis be unavoidable.In addition, in the preparation of active ink, the introducing of buffer solution, to active ink body
Frenulum carrys out great hidden danger, on the one hand brings challenges to the printing smoothness performance of ink on a printer；On the other hand, buffer solution
In component can be precipitated from ink with the time, easily block ink pipe, and cause plug.
Invention content
For disadvantage mentioned above, the purpose of the present invention is to provide a kind of storage stability is good and stablize not in storing process
The digit printing active liquid dyestuff of hydrolysis.
The technology contents of the present invention are a kind of digit printing active liquid dyestuff, it is characterized in that it contains useful the following general formula
（1）The reactive dye of expression：
Wherein D is the aromatic compound that benzene or naphthalene frenulum have sulfuric acid ester ethyl sulfone；Li+ x.Na+ yX and y is big in ion pair
In zero number, and x:The ratio of y is 1:5~5:1.
In above-mentioned digit printing active liquid dyestuff, general formula（1）The weight concentration of the reactive dye of expression is 20~50%.
Ethylene sulfuryl reactive dye are a kind of products through beta-hydroxyethyl sulfuryl sulphate activity dyestuff hydrolysis gained.Due to water
The hydrolysis of soluble group leaves away and the solubility of dyestuff is caused to be greatly reduced, and is difficult to the needs for meeting production application, thus this hair
Bright is that lithium salts/sodium salt of certain content is introduced in the structure of vinyl-sulfone reactive dyes as ion pair, can reduce because
Beta-hydroxyethyl sulfone sulfate（SES）It is hydrolyzed into ethylene sulfuryl（VS）The decline of colorant dissolubility caused by afterwards, it is ensured that dyestuff is higher
Dissolubility and the stability that stores for a long time.
Another object of the present invention is to provide the preparation method of above-mentioned digit printing active liquid dyestuff.
A kind of preparation method of digit printing active liquid dyestuff, includes the following steps：
（A）, hydroxyethyl sulfone sulfate reactive dye be configured to weight concentration be 1~10% aqueous dye solutions；
（B）, addition mixed base adjusts solution in above-mentioned aqueous dye solutions pH value be 9~11, and hydrolysis 6~10 is small under stiring
When；Mixed base is made of lithium carbonate and sodium carbonate, and the molar ratio of lithium carbonate and sodium carbonate is 1:0.5~1:5；
（C）, step（B）The solution of gained cools to -5 DEG C~5 DEG C, with the hydrochloric acid conditioning solution pH value that weight concentration is 1~5%
For 2~4.5 so that dyestuff is precipitated；Then it filters that dyestuff is precipitated；
（D）, step（C）In the salt acid elution 2~3 times that dyestuff weight concentration is 1~5% is precipitated, be then dried in vacuo, then
Add in the dyestuff slurries that water is made 10~20%；
（E）, with mixed base regulating step（D）In dyestuff slurries obtained pH value to 7, obtain finished product digit printing active liquid dye
Material；Mixed base is made of lithium carbonate and sodium carbonate, and the molar ratio of lithium carbonate and sodium carbonate is 1:0.5~1:5.
The possessed compared with prior art advantage of the present invention is：The present invention has good storage stability and is storing
Stablize unhydrolyzed feature in the process.
Specific embodiment
Embodiment 1,
（A）, following formula（2）Cyan beta-hydroxyethyl sulfuryl sulphate activity dyestuff be configured to weight concentration be 5% aqueous dye solutions；
（B）, addition mixed base adjusts solution in above-mentioned aqueous dye solutions pH value be 10, and hydrolyze 8 hours under stiring；Mixing
Alkali is made of lithium carbonate and sodium carbonate, and the molar ratio of lithium carbonate and sodium carbonate is 1:0.5；
（C）, step（B）The solution of gained cools to 0 DEG C, and the hydrochloric acid conditioning solution pH value for being 3% with weight concentration is 3 so that dye
Material is precipitated；Then it filters that dyestuff is precipitated；
（D）, step（C）In the salt acid elution 2 times that dyestuff weight concentration is 3% is precipitated, be then dried in vacuo, add water
15% dyestuff slurries are made；
（E）, with mixed base regulating step（D）In dyestuff slurries obtained pH value to 7, obtain following formula（2a）Cyan finished product it is digital
Stamp active liquid dyestuff；Mixed base is made of lithium carbonate and sodium carbonate, and the molar ratio of lithium carbonate and sodium carbonate is 1:0.5；Formula
（2a）Middle Li+ x.Na+ yX:y=2:1；
（F）, step（E）In finished product digit printing active liquid dyestuff obtained concentration, it is 30% to make reactive dye weight concentration.
Embodiment 2-5,
Using the method shown in embodiment 1, by formula（2）Dyestuff change the following structural formula of identical weight into respectively（3）, formula
（4）, formula（5）Or formula（6）Dyestuff, i.e., respectively to deserved following formula（3a）, formula（4a）, formula（5a）Or formula（6a）Cyan finished product number
Code stamp reactive dye, Li in formula+ x.Na+ yX:y=2:1, raw material and corresponding finished product are as shown in table 1 below；
Embodiment 6,
（A）, following formula（7）Yellow beta-hydroxyethyl sulfuryl sulphate activity dyestuff be configured to weight concentration be 5% aqueous dye solutions；
（B）, addition mixed base adjusts solution in above-mentioned aqueous dye solutions pH value be 10, and hydrolyze 8 hours under stiring；Mixing
Alkali is made of lithium carbonate and sodium carbonate, and the molar ratio of lithium carbonate and sodium carbonate is 1:1；
（C）, step（B）The solution of gained cools to 0 DEG C, and the hydrochloric acid conditioning solution pH value for being 3% with weight concentration is 3 so that dye
Material is precipitated；Then it filters that dyestuff is precipitated；
（D）, step（C）In the salt acid elution 2 times that dyestuff weight concentration is 3% is precipitated, be then dried in vacuo, add water
15% dyestuff slurries are made；
（E）, with mixed base regulating step（D）In dyestuff slurries obtained pH value to 7, obtain following formula（7a）Yellow finished product it is digital
Stamp active liquid dyestuff；Mixed base is made of lithium carbonate and sodium carbonate, and the molar ratio of lithium carbonate and sodium carbonate is 1:1；Formula
（7a）Middle Li+ x.Na+ yX:y=1:1；
（F）, step（E）In finished product digit printing active liquid dyestuff obtained concentration, it is 30% to make reactive dye weight concentration.
Embodiment 7,
（A）, following formula（8）Red beta-hydroxyethyl sulfuryl sulphate activity dyestuff be configured to weight concentration be 5% aqueous dye solutions；
（B）, addition mixed base adjusts solution in above-mentioned aqueous dye solutions pH value be 10, and hydrolyze 8 hours under stiring；Mixing
Alkali is made of lithium carbonate and sodium carbonate, and the molar ratio of lithium carbonate and sodium carbonate is 1:2；
（C）, step（B）The solution of gained cools to 0 DEG C, and the hydrochloric acid conditioning solution pH value for being 3% with weight concentration is 3 so that dye
Material is precipitated；Then it filters that dyestuff is precipitated；
（D）, step（C）In the salt acid elution 2 times that dyestuff weight concentration is 3% is precipitated, be then dried in vacuo, add water
15% dyestuff slurries are made；
（E）, with mixed base regulating step（D）In dyestuff slurries obtained pH value to 7, obtain following formula（8a）Red finished product it is digital
Stamp active liquid dyestuff；Mixed base is made of lithium carbonate and sodium carbonate, and the molar ratio of lithium carbonate and sodium carbonate is 1:2；Formula
（8a）Middle Li+ x.Na+ yX:y=1:2；
（F）, step（E）In finished product digit printing active liquid dyestuff obtained concentration, it is 30% to make reactive dye weight concentration.
Embodiment 8,
（A）, following formula（9）Orange beta-hydroxyethyl sulfuryl sulphate activity dyestuff be configured to weight concentration be 5% aqueous dye solutions；
（B）, addition mixed base adjusts solution in above-mentioned aqueous dye solutions pH value be 10, and hydrolyze 8 hours under stiring；Mixing
Alkali is made of lithium carbonate and sodium carbonate, and the molar ratio of lithium carbonate and sodium carbonate is 1:3；
（C）, step（B）The solution of gained cools to 0 DEG C, and the hydrochloric acid conditioning solution pH value for being 3% with weight concentration is 3 so that dye
Material is precipitated；Then it filters that dyestuff is precipitated；
（D）, step（C）In the salt acid elution 2 times that dyestuff weight concentration is 3% is precipitated, be then dried in vacuo, add water
15% dyestuff slurries are made；
（E）, with mixed base regulating step（D）In dyestuff slurries obtained pH value to 7, obtain following formula（9a）Orange finished product it is digital
Stamp active liquid dyestuff；Mixed base is made of lithium carbonate and sodium carbonate, and the molar ratio of lithium carbonate and sodium carbonate is 1:3；Formula
（9a）Middle Li+ x.Na+ yX:y=1:3；
（F）, step（E）In finished product digit printing active liquid dyestuff obtained concentration, it is 30% to make reactive dye weight concentration.
Embodiment 9-30,
Using the method shown in embodiment 8, but by formula（9）Dyestuff change the following general structure of identical weight number into（）'s
Dyestuff is to get following formula（a）In finished product digit printing active liquid dyestuff, Li in following formula+ x.Na+ yX:y=1:3；
Wherein, D1 xy、D2 xy3 are shown in Table for the concrete structure with the group shown in table 2, group；D1´ xy、D2´ xyIt represents respectively
D1 xyWith D2 xyIn-CH2CH2OSO3It is hydrolyzed into-CH=CH2Group, can refer to patent CN1745147；
Embodiment 31,
（A）, 7.8g following formulas（2）Cyan beta-hydroxyethyl sulfuryl sulphate activity dyestuff and 2.2g following formulas（31）Yellow beta-hydroxyethyl
Sulfone sulfate reactive dye are configured to the aqueous dye solutions that weight concentration is 5%；
（B）, addition mixed base adjusts solution in above-mentioned aqueous dye solutions pH value be 10, and hydrolyze 8 hours under stiring；Mixing
Alkali is made of lithium carbonate and sodium carbonate, and the molar ratio of lithium carbonate and sodium carbonate is 1:2；
（C）, step（B）The solution of gained cools to 0 DEG C, and the hydrochloric acid conditioning solution pH value for being 3% with weight concentration is 3 so that dye
Material is precipitated；Then it filters that dyestuff is precipitated；
（D）, step（C）In the salt acid elution 2 times that dyestuff weight concentration is 3% is precipitated, be then dried in vacuo, add water
15% dyestuff slurries are made；
（E）, with mixed base regulating step（D）In dyestuff slurries obtained pH value to 7, obtain by following formula（2a）And following formula（31a）
The black finished product digit printing active liquid dyestuff of composition；Mixed base is made of lithium carbonate and sodium carbonate, lithium carbonate and sodium carbonate
Molar ratio be 1:2；Formula（2a）Middle Li+ x.Na+ yX:y=1:2, formula（31a）Li+ x.Na+ yX:y=1:2；
（F）, step（E）In finished product digit printing active liquid dyestuff obtained concentration, it is 30% to make reactive dye weight concentration.
Embodiment 32,
（A）, 6.8g following formulas（2）Cyan beta-hydroxyethyl sulfuryl sulphate activity dyestuff, 2.7g following formulas（9）Yellow beta-hydroxyethyl sulfuryl
Sulphate activity dyestuff and 0.3g following formulas（32）Red beta-hydroxyethyl sulfuryl sulphate activity dyestuff be configured to weight concentration as 5%
Aqueous dye solutions；Formula（32）Middle R1=H, R2=H；
（B）, addition mixed base adjusts solution in above-mentioned aqueous dye solutions pH value be 10, and hydrolyze 8 hours under stiring；Mixing
Alkali is made of lithium carbonate and sodium carbonate, and the molar ratio of lithium carbonate and sodium carbonate is 1:3；
（C）, step（B）The solution of gained cools to 0 DEG C, and the hydrochloric acid conditioning solution pH value for being 3% with weight concentration is 3 so that dye
Material is precipitated；Then it filters that dyestuff is precipitated；
（D）, step（C）In the salt acid elution 2 times that dyestuff weight concentration is 3% is precipitated, be then dried in vacuo, add water
15% dyestuff slurries are made；
（E）, with mixed base regulating step（D）In dyestuff slurries obtained pH value to 7, obtain by following formula（2a）, following formula（9a）With
Following formula（32a）The black finished product digit printing active liquid dyestuff of composition；Mixed base is made of lithium carbonate and sodium carbonate, lithium carbonate
Molar ratio with sodium carbonate is 1:3；Formula（2a）Middle Li+ x.Na+ yX:y=1:3, formula（9a）Middle Li+ x.Na+ yX:y=1:3, formula
（32a）Middle Li+ x.Na+ yX:y=1:3, formula（32a）Middle R1=H, R2=H；
（F）By step（E）In finished product digit printing active liquid dyestuff obtained concentration, make the reactive dye weight concentration be
30%.
Embodiment 33,
By the formula in embodiment 32（32）Red beta-hydroxyethyl sulfuryl sulphate activity dyestuff in R1= SO3 -, R2=H, other conditions
It is constant to get by formula（2a）, formula（9a）And formula（32a）The black finished product digit printing reactive dye of composition, formula（2a）Middle Li+ x.Na+ yX:y=1:3, formula（9a）Middle Li+ x.Na+ yX:y=1:3, formula（32a）Middle Li+ x.Na+ yX:y=1:3, formula（32a）In
R1= SO3 -, R2=H。
Embodiment 34,
By the formula in embodiment 32（32）Red beta-hydroxyethyl sulfuryl sulphate activity dyestuff in R1=H, R2= SO3 -, other
Part is constant to get by formula（2a）, formula（9a）And formula（32a）The black finished product digit printing reactive dye of composition, formula（2a）Middle Li+ x.Na+ yX:y=1:3, formula（9a）Middle Li+ x.Na+ yX:y=1:3, formula（32a）Middle Li+ x.Na+ yX:y=1:3, formula（32a）In
R1=H, R2= SO3 -。
Embodiment 35,
By the formula in embodiment 32（32）Red beta-hydroxyethyl sulfuryl sulphate activity dyestuff in R1= SO3 -, R2= SO3 -, it is other
Condition is constant to get by formula（2a）, formula（9a）And formula（32a）The black finished product digit printing reactive dye of composition, formula（2a）In
Li+ x.Na+ yX:y=1:3, formula（9a）Middle Li+ x.Na+ yX:y=1:3, formula（32a）Middle Li+ x.Na+ yX:y=1:3, formula（32a）
Middle R1= SO3 -, R2= SO3 -。
Claims (2)
1. a kind of digit printing active liquid dyestuff, it is characterized in that it contains useful the following general formula（1）The reactive dye of expression：
Wherein D is the aromatic compound that benzene or naphthalene frenulum have sulfuric acid ester ethyl sulfone；Li+ x.Na+ yIn ion pair x and y be more than
Zero number, and x:The ratio of y is 1:5~5:1.
2. a kind of preparation method of digit printing active liquid dyestuff, includes the following steps：
（A）, beta-hydroxyethyl sulfuryl sulphate activity dyestuff is configured to the aqueous dye solutions that weight concentration is 1~10%；
（B）, add in above-mentioned aqueous dye solutions mixed base and adjust the pH value of solution as 9~11, and hydrolyze 6~10 under stiring
Hour；Mixed base is made of lithium carbonate and sodium carbonate, and the molar ratio of lithium carbonate and sodium carbonate is 1:0.5~1:5；
（C）, by step（B）The solution of gained cools to -5 DEG C~5 DEG C, with the hydrochloric acid conditioning solution pH that weight concentration is 1~5%
It is worth for 2~4.5 so that dyestuff is precipitated；Then it filters that dyestuff is precipitated；
（D）, by step（C）In the salt acid elution 2~3 times that dyestuff weight concentration is 1~5% is precipitated, be then dried in vacuo,
Add the dyestuff slurries that water is made 10~20%；
（E）, again use mixed base regulating step（D）In dyestuff slurries obtained pH value to 7, obtain finished product digit printing active liquid
Dyestuff；Mixed base is made of lithium carbonate and sodium carbonate, and the molar ratio of lithium carbonate and sodium carbonate is 1:0.5~1:5.
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108690371A (en) * | 2018-06-28 | 2018-10-23 | 天津晶丽数码科技有限公司 | A kind of salt-free liquid dyes of double vinyl-sulfone reactives, preparation method and application |
| CN108690370A (en) * | 2018-06-28 | 2018-10-23 | 天津晶丽数码科技有限公司 | A kind of storage stability high salt-free active liquid dyestuff, its preparation method and purposes |
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Application publication date: 20180615 |