CN101948631B - A kind of K type active light-resistant orange azo dye and preparation method thereof - Google Patents
A kind of K type active light-resistant orange azo dye and preparation method thereof Download PDFInfo
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- CN101948631B CN101948631B CN201010236146.8A CN201010236146A CN101948631B CN 101948631 B CN101948631 B CN 101948631B CN 201010236146 A CN201010236146 A CN 201010236146A CN 101948631 B CN101948631 B CN 101948631B
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- 0 *c1cc2cc(N)ccc2c(O)c1 Chemical compound *c1cc2cc(N)ccc2c(O)c1 0.000 description 1
- WCJHJTRBDUOQJE-UHFFFAOYSA-N [N]OS(c1cc(O)c(ccc(NC(N2)=NC(Cl)=NC2Cl)c2)c2c1)(=O)=O Chemical compound [N]OS(c1cc(O)c(ccc(NC(N2)=NC(Cl)=NC2Cl)c2)c2c1)(=O)=O WCJHJTRBDUOQJE-UHFFFAOYSA-N 0.000 description 1
Abstract
The present invention discloses a kind of K type active light-resistant orange azo dye and preparation method thereof, comprises hindered amine group in the molecular structure of these reactive dyestuffs.These reactive dyestuffs compared with reactive brilliant orange K-R, dyeing behavior and every wet colour fastness close, all there is very high dye uptake and degree of fixation, but sunlight fastness is improved significantly.
Description
Technical field
The present invention relates to a kind of organic dye, particularly relate to a kind of K type active light-resistant orange azo dye.
Background technology
Reactive dyestuffs, because it is bright in colour, chromatogram is wide, fastness is excellent and application art is simple, low price, are thus developed into the dye that natural fiber dyeing rate of utilization is the highest, are also the fastest dyes of development in recent years.But reactive dyestuffs also expose in application process, and dye utilization rate is low, DYED FABRICS fastness to wet rubbing and the relatively low shortcoming of light coloured variety sunlight fastness.These shortcomings how overcoming reactive dyestuffs have become the emphasis problem of current reactive dyestuffs research and development.
Summary of the invention
The object of this invention is to provide a kind of K type active light-resistant orange azo dye, it has good photooxidation resistant performance, can make up the deficiency of existing reactive orange azo-dye sunlight fastness aspect of performance.
A kind of K type active light-resistant orange azo dye, is characterized in that containing hindered amine group in molecular structure, represents with following general formula:
R is worked as in formula
1for 4 benzoic acid ester group-1-R
3-2,2,6,6-tetramethyl piperidines or 4-benzoylamino-1-R
3during-2,2,6,6-tetramethyl piperidine, R
2for ortho position or a position or contraposition sulfo group substituted-phenyl, or 2,4-disulfo substituted-phenyl, or 2,5-disulfo substituted-phenyl; Work as R
1for ortho position or a position or contraposition sulfo group substituted-phenyl, or 2,4-disulfo substituted-phenyl, or during 2,5-disulfo substituted-phenyl, R
2for 4 benzoic acid ester group-1-R
3-2,2,6,6-tetramethyl piperidines or 4-benzoylamino-1-R
3-2,2,6,6-tetramethyl piperidines; Wherein R
3for H or methyl, the carbonyl in above-mentioned phenylformic acid ester group or benzoylamino is positioned at the ortho position of azo-group or the amino be connected with phenyl ring or a position or contraposition.
A kind of preparation method of K type active light-resistant orange azo dye, it is characterized in that first taking cyanuric chloride adds in frozen water, stirring to pulp at least 10 minutes, and then in 1 hour, evenly add J acid solution carry out condensation reaction, control reacting liquid pH value and be less than 4, below 10 DEG C, react certain hour, by termination reaction when existing without J acid in amino indicator detection reaction liquid, and by reacting liquid filtering, obtain condensated liquid for subsequent use; Diazotisation methods is to the amino substituted benzoyl perester radical of 4--1-R routinely
3-2,2,6,6-tetramethyl piperidines or the amino substituted benzene formyl amido of 4--1-R
3-2,2,6,6-tetramethyl piperidines or substituted aniline carry out diazotization reaction, obtain temperature lower than the diazonium salt solution of 5 DEG C; Then the diazonium salt solution obtained is joined in above-mentioned gained condensated liquid equably and carry out coupled reaction, add rear tune pH=4 ~ 5, and continue at less than 10 DEG C stirring reactions 0.5 ~ 2 hour, adjust pH=6.8 ~ 7 again, continue stirring reaction certain hour again, with oozing termination reaction when the detection of circle method exists without cyanuric chloride and J acid condenses, obtain coupling solution for subsequent use; By substituted aniline or the amino substituted benzoyl perester radical of 4--1-R
3-2,2,6,6-tetramethyl piperidines or the amino substituted benzene formyl amido of 4--1-R
3-2,2,6,6-tetramethyl piperidine solution warms to 40 DEG C, more above-mentioned gained coupling solution was added equably in 1 hour, add rear adjustment pH=6 ~ 7, continue stirring reaction certain hour, detect without substituted aniline or the amino substituted benzoyl perester radical of 4--1-R with amino indicator
3-2,2,6,6-tetramethyl piperidines or the amino substituted benzene formyl amido of 4--1-R
3termination reaction when-2,2,6,6-tetramethyl piperidines exist; Add salt by reaction solution volume 10 ~ 25% again to saltout, filter, obtain filter cake, in filter cake, add the pH buffer reagent of filter cake weight 1 ~ 5%, vacuum-drying at 85 DEG C after mixing, obtain K type active light-resistant orange azo dye; The amino substituted benzoyl perester radical of wherein said 4--1-R
3-2,2,6,6-tetramethyl piperidines or the amino substituted benzene formyl amido of 4--1-R
3r in-2,2,6,6-tetramethyl piperidines
3for H or methyl, the amino position replaced is the ortho position of phenylformic acid ester group or benzoylamino or a position or contraposition; Described substituted aniline is ortho position or a position or contraposition aniline sulfonic acid, or 2,4-disulfo aniline, or 2,5-disulfo aniline; Described amino indicator is made up of 1 part of p-N, N-dimethylaminobenzaldehyde, 95 parts of ethanol and 5 parts of concentrated hydrochloric acid mixing solutionss; The consumption mol ratio of described cyanuric chloride and J acid is 1 ~ 1.2: 1; The amino substituted benzoyl perester radical of described 4--1-R
3-2,2,6,6-tetramethyl piperidines or the amino substituted benzene formyl amido of 4--1-R
3the consumption mol ratio of-2,2,6,6-tetramethyl piperidines and J acid is 1: 1; The consumption mol ratio of described substituted aniline and J acid is 1: 1; Described salt is salt or Sodium sulfate anhydrous.min(99); Described pH buffer reagent is the mixture of a certain proportion of Sodium phosphate dibasic and SODIUM PHOSPHATE, MONOBASIC.
K type active light-resistant orange azo dye provided by the invention compared with reactive brilliant orange K-R, dyeing behavior and every wet colour fastness close, all there is very high dye uptake and degree of fixation, but sunlight fastness is improved significantly.
Embodiment
Below by embodiment, the present invention is described.
Embodiment 1, the synthesis of active fast light orange KA
1, the preparation of cyanuric chloride and J acid condensation reaction solution
In the 250mL four-hole boiling flask that agitator, dropping funnel and thermometer are housed, add 15g trash ice, 10mL water and 0.011mol cyanuric chloride respectively 0 DEG C of making beating 30 minutes, then in 1 hour, be added dropwise to pH=7 ~ 8, J acid solution that J acid content is 0.01mol, after adding, the pH value keeping reaction solution is 2 ~ 3, continues stirring reaction 3 hours at 5 ~ 8 DEG C, liquid is detected without after J acid existence with amino indicator, stopped reaction, filters, must clarify condensated liquid for subsequent use.Reaction formula is as follows:
2, the preparation of 4-(PABA ester group)-2,2,6,6-tetramethyl piperidine diazonium salt solution
In 150mL beaker, add 30mL water, 4-(PABA ester group)-2,2,6, the 6-tetramethyl piperidine of 0.01mol, 3.5mL30% hydrochloric acid, starts stirring, and aminocompound is dissolved completely, puts into ice-water bath and is cooled to 0 DEG C.0.0105mol Sodium Nitrite is dissolved in 2mL water, 0 DEG C is cooled in ice-water bath, join fast in aminocompound, the pH value adding rear maintenance reaction solution is less than 3, temperature continues stirring reaction lower than 5 DEG C, after 2 hours, diazotization reaction is complete, now reaction solution is blue to congo-red test paper, be micro-blueness to starch potassium iodide paper, add appropriate thionamic acid to reaction solution to starch potassium iodide paper nondiscoloration to reaction solution, then obtain 4-(PABA ester group)-2,2,6,6-tetramethyl piperidine diazonium salt solution is for subsequent use.Reaction formula is as follows:
3, the preparation of coupling solution
Whole cyanuric chloride of above-mentioned preparation and J acid condensation reaction solution and 10g trash ice is added in 250mL beaker, start and stir and be cooled to 0 DEG C, then whole 4-(PABA ester group)-2 of above-mentioned preparation are added fast, 2, 6, 6-tetramethyl piperidine diazonium salt solution carries out coupled reaction, after stirring, trisodium phosphate solution with 20% adjusts pH=4.8 ~ 5.1, and continue stirring reaction 1 hour in 4 ~ 6 DEG C, and then continue stirring reaction after adjusting pH=6.8 ~ 7 with 20% sodium carbonate solution, until with oozing in circle method detection reaction liquid after the completely dissolve of cyanuric chloride and J acid condenses, termination reaction, obtain coupling solution for subsequent use.Reaction formula is as follows:
4, the synthesis of dyestuff
The Sodium sulfanilate solution stirring of 0.01mol is warming up to 40 DEG C, the whole coupling solution of above-mentioned gained is added equably in 1 hour, after stirring, control pH=6.5 ~ 6.7, temperature of reaction is 40 DEG C, continue stirring reaction certain hour, termination reaction when existing without Sodium sulfanilate with amino indicator detection; Salt is added immediately by 20% of reaction solution volume, be cooled to room temperature while stirring, under room temperature, continue stirring again saltout for 1 hour, filter, obtain dyestuff filter-cakes, in dyestuff filter-cakes, add the SODIUM PHOSPHATE, MONOBASIC of filter cake weight 2% Sodium phosphate dibasic and 1%, after mixing, at 85 DEG C, carry out vacuum-drying, pulverize, active fast light orange KA can be obtained.Reaction formula is as follows:
Embodiment 2, the synthesis of active fast light orange KB
The molecular structural formula of active fast light orange KB is as follows:
The preparation process of active fast light orange KB, with embodiment 1, is by the 4-(PABA ester group)-2,2,6 in embodiment 1,6-tetramethyl piperidine replaces with 4-(4-aminobenzoyl amido)-1,2,2,6,6-pentamethvl, active fast light orange KB.
Embodiment 3, the synthesis of active fast light orange KC
1, the preparation of cyanuric chloride and J acid condensation reaction solution
The preparation process of cyanuric chloride and J acid condensation reaction solution is with embodiment 1.
2, the preparation of Diazosalt of sulfanilic acid solution
In 100mL beaker, add 10mL water, 0.01mol Sulphanilic Acid, starts stirring, with in sodium carbonate solution and regulate pH=7.5, make it dissolve, then add the Sodium Nitrite of 0.0105mol, put into ice-water bath after mixed dissolution and be cooled to 0 DEG C, then load in dropping funnel for subsequent use.Water 17ml is added in 150ml beaker, add the concentrated hydrochloric acid preparation hydrochloric acid soln of 3ml36% more while stirring, hydrochloric acid soln is cooled to 0 DEG C, again the mixed solution in dropping funnel was added equably in hydrochloric acid soln in 1 hour and carry out diazotization reaction, the pH value adding rear maintenance reaction solution is less than 3, temperature continues stirring reaction lower than 5 DEG C, after 2 hours, diazotization reaction is complete, now reaction solution is blue to congo-red test paper, be micro-blueness to starch potassium iodide paper, appropriate thionamic acid is added to reaction solution to starch potassium iodide paper nondiscoloration to reaction solution, then obtain Diazosalt of sulfanilic acid solution for standby.Reaction formula is as follows:
3, the preparation of coupling solution
Whole cyanuric chloride of above-mentioned preparation and J acid condensation reaction solution and 10g trash ice is added in 250mL beaker, start and stir and be cooled to 0 DEG C, then the whole Diazosalt of sulfanilic acid solution adding above-mentioned preparation fast carry out coupled reaction, after stirring, trisodium phosphate solution with 20% adjusts pH=4.8 ~ 5.1, and continue stirring reaction 1 hour in 4 ~ 6 DEG C, and then continue stirring reaction after adjusting pH=6.8 ~ 7 with 20% sodium carbonate solution, until with oozing in circle method detection reaction liquid after the completely dissolve of cyanuric chloride and J acid condenses, termination reaction, obtain coupling solution for subsequent use.Reaction formula is as follows:
4, the synthesis of dyestuff
By 0.01mol4-(PABA ester group)-2, 2, 6, 6-tetramethyl piperidine puts into 250mL beaker, add 20mL water, adding 2mL concentrated hydrochloric acid while stirring makes it dissolve, continue stir and be warming up to 40 DEG C, the whole coupling solution of above-mentioned gained is added equably in 1 hour, after stirring, control pH=6.5 ~ 6.7, temperature of reaction is 40 DEG C, continue stirring reaction 2 ~ 4 hours, with 4-(PABA ester group)-2 in amino indicator detection reaction liquid, 2, 6, after 6-tetramethyl piperidine all disappears, reaction is reached home, salt is added immediately by 20% of reaction solution volume, be cooled to room temperature while stirring, under room temperature, continue stirring again saltout for 1 hour, filter, obtain dyestuff filter-cakes, the SODIUM PHOSPHATE, MONOBASIC of filter cake weight 2% Sodium phosphate dibasic and 1% is added in dyestuff filter-cakes, after mixing, vacuum-drying is carried out at 85 DEG C, pulverize, obtain active fast light orange KC.Reaction formula is as follows:
Embodiment 4, the synthesis of active fast light orange KD
The molecular structural formula of active fast light orange KD is as follows:
The preparation process of active fast light orange KD is with embodiment 3, just the Sulphanilic Acid in embodiment 3 is replaced with m-sulfanilic acid, 4-(PABA ester group)-2,2,6,6-tetramethyl piperidine replaces with 4-(4-aminobenzoyl amido)-1,2,2,6,6-pentamethvl, the fast light orange KD of resistance to activity.
Embodiment 5: dyestuff is purified and performance test
Take the thick product 10g of active fast light orange KA, dissolve with 90mLDMF, filter, filtrate is added dropwise to lentamente in the 360mL acetone that stirred, after adding, continue to stir certain hour, filter, use washing with acetone filter cake, then dry at 80 DEG C, crushed after being dried, obtains the fast light orange KA of salt-free activity.Adopt same procedure, salt-free commercial dye reactive brilliant orange K-R can be prepared, salt-free activity is fast light orange KB, salt-free activity is fast light orange KC, salt-free activity is fast light orange KD; According to national standard method to the fast light orange KA of the salt-free activity of gained, salt-free activity is fast light orange KB, salt-free activity is fast light orange KC, salt-free activity is fast light, and orange KD and salt-free commercial dye reactive brilliant orange K-R carries out dyeing behavior and fastness ability test, result shows active fast light orange KA, active fast light orange KB, active fast light orange KC and the fast light orange KD of activity is all reactive orange azo-dyes bright in colour; Active fast light orange KA, active fast light orange KB, active fast light orange KC and the fast light maximum absorption wavelength of orange KD of activity, the dye uptake of dyestuff and degree of fixation all close with commercial dye reactive brilliant orange K-R; But the gorgeous orange K-R of the equal specific activity of sunlight fastness exceeds 0.5 ~ 1 grade.
4-(PABA ester group)-2,2,6 used in above-mentioned embodiment, 6-tetramethyl piperidine can by 4-(2-benzaminic acid ester group)-2,2,6,6-tetramethyl piperidine, or 4-(3-benzaminic acid ester group)-2,2,6,6-tetramethyl piperidine, or 4-(2-benzaminic acid ester group)-1,2,2,6,6-pentamethvl, or 4-(3-benzaminic acid ester group)-1,2,2,6,6-pentamethvl, or 4-(PABA ester group)-1,2, the replacements such as 2,6,6-pentamethvl; 4-(4-aminobenzoyl amido)-1,2,2,6,6-pentamethvl can by 4-(2-aminobenzoyl amido)-2,2,6,6-tetramethyl piperidine, or 4-(3-AB base)-2,2,6,6-tetramethyl piperidine, or 4-(4-aminobenzoyl amido)-2,2,6,6-tetramethyl piperidine, or 4-(2-aminobenzoyl amido)-1,2,2,6,6-pentamethvl, or 4-(3-AB base)-1,2,2,6,6-pentamethvl replaces; In above-mentioned embodiment, contraposition or a bit amino Phenylsulfonic acid also can by ortho position aniline sulfonic acids, or aniline-2,4-disulfonic acid, or aniline-2,5-disulfonic acid replaces.Adopt similar synthetic method, gained orange dye dyeing behavior and every wet colour fastness and reactive brilliant orange K-R close, all there is very high dye uptake and degree of fixation, but sun-resistant Performance Ratio reactive brilliant orange K-R exceeds 0.5 ~ 1 grade.
Claims (2)
1. a K type active light-resistant orange azo dye, is characterized in that containing hindered amine group in molecular structure, represents with following general formula:
R is worked as in formula
1for 4 benzoic acid ester group-1-R
3-2,2,6,6-tetramethyl piperidines or 4-benzoylamino-1-R
3during-2,2,6,6-tetramethyl piperidine, R
2for ortho position or a position or contraposition sulfo group substituted-phenyl, or 2,4-disulfo substituted-phenyl, or 2,5-disulfo substituted-phenyl; Work as R
1for ortho position or a position or contraposition sulfo group substituted-phenyl, or 2,4-disulfo substituted-phenyl, or during 2,5-disulfo substituted-phenyl, R
2for 4 benzoic acid ester group-1-R
3-2,2,6,6-tetramethyl piperidines or 4-benzoylamino-1-R
3-2,2,6,6-tetramethyl piperidines; Wherein R
3for H or methyl, the carbonyl in above-mentioned phenylformic acid ester group or benzoylamino is positioned at the ortho position of azo-group or the amino be connected with phenyl ring or a position or contraposition.
2. the preparation method of a kind of K type active light-resistant orange azo dye as claimed in claim 1, it is characterized in that first taking cyanuric chloride adds in frozen water, stirring to pulp at least 10 minutes, and then in 1 hour, evenly add J acid solution carry out condensation reaction, control reacting liquid pH value and be less than 4, below 10 DEG C, react certain hour, by termination reaction when existing without J acid in amino indicator detection reaction liquid, and by reacting liquid filtering, obtain condensated liquid for subsequent use; Diazotisation methods is to the amino substituted benzoyl perester radical of 4--1-R routinely
3-2,2,6,6-tetramethyl piperidines or the amino substituted benzene formyl amido of 4--1-R
3-2,2,6,6-tetramethyl piperidines or substituted aniline carry out diazotization reaction, obtain temperature lower than the diazonium salt solution of 5 DEG C; Then the diazonium salt solution obtained is joined in above-mentioned gained condensated liquid equably and carry out coupled reaction, add rear tune pH=4 ~ 5, and continue at less than 10 DEG C stirring reactions 0.5 ~ 2 hour, adjust pH=6.8 ~ 7 again, continue stirring reaction certain hour again, with oozing termination reaction when the detection of circle method exists without cyanuric chloride and J acid condenses, obtain coupling solution for subsequent use; By substituted aniline or the amino substituted benzoyl perester radical of 4--1-R
3-2,2,6,6-tetramethyl piperidines or the amino substituted benzene formyl amido of 4--1-R
3-2,2,6,6-tetramethyl piperidine solution warms to 40 DEG C, more above-mentioned gained coupling solution was added equably in 1 hour, add rear adjustment pH=6 ~ 7, continue stirring reaction certain hour, detect without substituted aniline or the amino substituted benzoyl perester radical of 4--1-R with amino indicator
3-2,2,6,6-tetramethyl piperidines or the amino substituted benzene formyl amido of 4--1-R
3termination reaction when-2,2,6,6-tetramethyl piperidines exist; Add salt by reaction solution volume 10 ~ 25% again to saltout, filter, obtain filter cake, in filter cake, add the pH buffer reagent of filter cake weight 1 ~ 5%, vacuum-drying at 85 DEG C after mixing, obtain K type active light-resistant orange azo dye; The amino substituted benzoyl perester radical of wherein said 4--1-R
3-2,2,6,6-tetramethyl piperidines or the amino substituted benzene formyl amido of 4--1-R
3r in-2,2,6,6-tetramethyl piperidines
3for H or methyl, the amino position replaced is the ortho position of phenylformic acid ester group or benzoylamino or a position or contraposition; Described substituted aniline is ortho position or a position or contraposition aniline sulfonic acid, or 2,4-disulfo aniline, or 2,5-disulfo aniline; Described amino indicator is made up of 1 part of p-N, N-dimethylaminobenzaldehyde, 95 parts of ethanol and 5 parts of concentrated hydrochloric acid mixing solutionss; The consumption mol ratio of described cyanuric chloride and J acid is 1 ~ 1.2: 1; The amino substituted benzoyl perester radical of described 4--1-R
3-2,2,6,6-tetramethyl piperidines or the amino substituted benzene formyl amido of 4--1-R
3the consumption mol ratio of-2,2,6,6-tetramethyl piperidines and J acid is 1: 1; The consumption mol ratio of described substituted aniline and J acid is 1: 1; Described salt is salt or Sodium sulfate anhydrous.min(99); Described pH buffer reagent is the mixture of a certain proportion of Sodium phosphate dibasic and SODIUM PHOSPHATE, MONOBASIC.
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| CN102286216A (en) * | 2011-06-29 | 2011-12-21 | 天津德凯化工股份有限公司 | Orange nylon active dyestuff and preparation method thereof |
| JP5919235B2 (en) * | 2012-09-27 | 2016-05-18 | 富士フイルム株式会社 | Pigment composition, colored curable composition, color filter for solid-state imaging device and method for producing the same, solid-state imaging device, pigment dispersion composition and method for producing the same, and compound |
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