CN101792613B - Yellow reactive dye for wool and preparation method and application thereof - Google Patents
Yellow reactive dye for wool and preparation method and application thereof Download PDFInfo
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- CN101792613B CN101792613B CN 200910242263 CN200910242263A CN101792613B CN 101792613 B CN101792613 B CN 101792613B CN 200910242263 CN200910242263 CN 200910242263 CN 200910242263 A CN200910242263 A CN 200910242263A CN 101792613 B CN101792613 B CN 101792613B
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- 210000002268 wool Anatomy 0.000 title claims abstract description 42
- 239000000985 reactive dye Substances 0.000 title claims abstract description 22
- 238000002360 preparation method Methods 0.000 title claims description 11
- 239000000835 fiber Substances 0.000 claims abstract description 29
- 239000002253 acid Substances 0.000 claims abstract description 15
- 238000005859 coupling reaction Methods 0.000 claims description 54
- 238000006243 chemical reaction Methods 0.000 claims description 50
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 44
- 238000004886 process control Methods 0.000 claims description 42
- 238000004043 dyeing Methods 0.000 claims description 39
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 claims description 36
- 239000007788 liquid Substances 0.000 claims description 34
- 230000008878 coupling Effects 0.000 claims description 30
- 238000010168 coupling process Methods 0.000 claims description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 30
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 24
- 235000010288 sodium nitrite Nutrition 0.000 claims description 24
- 238000003756 stirring Methods 0.000 claims description 24
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 22
- 238000010009 beating Methods 0.000 claims description 18
- 238000001514 detection method Methods 0.000 claims description 18
- 238000006482 condensation reaction Methods 0.000 claims description 14
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 12
- 229920002472 Starch Polymers 0.000 claims description 12
- IQFVPQOLBLOTPF-HKXUKFGYSA-L congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 claims description 12
- 239000000463 material Substances 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 235000019698 starch Nutrition 0.000 claims description 12
- 239000008107 starch Substances 0.000 claims description 12
- 239000011734 sodium Substances 0.000 claims description 10
- 229910052708 sodium Inorganic materials 0.000 claims description 8
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 6
- 238000004587 chromatography analysis Methods 0.000 claims description 6
- 238000006193 diazotization reaction Methods 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 6
- 230000008030 elimination Effects 0.000 claims description 6
- 238000003379 elimination reaction Methods 0.000 claims description 6
- 229910052710 silicon Inorganic materials 0.000 claims description 6
- 239000010703 silicon Substances 0.000 claims description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 6
- 235000017550 sodium carbonate Nutrition 0.000 claims description 6
- 238000005507 spraying Methods 0.000 claims description 6
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 claims description 2
- 229910052728 basic metal Inorganic materials 0.000 claims description 2
- 150000003818 basic metals Chemical group 0.000 claims description 2
- 229950000244 sulfanilic acid Drugs 0.000 claims description 2
- APRRQJCCBSJQOQ-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(N)=CC(S(O)(=O)=O)=CC2=C1 APRRQJCCBSJQOQ-UHFFFAOYSA-N 0.000 claims 2
- -1 2,3-propylene bromide acyl chlorides Chemical class 0.000 claims 1
- 239000000975 dye Substances 0.000 abstract description 34
- 238000005406 washing Methods 0.000 abstract description 28
- 230000009257 reactivity Effects 0.000 abstract description 3
- 239000003795 chemical substances by application Substances 0.000 abstract description 2
- CWJLXOUWYUQFHL-UHFFFAOYSA-N 2-bromoprop-2-enamide Chemical group NC(=O)C(Br)=C CWJLXOUWYUQFHL-UHFFFAOYSA-N 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 36
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 24
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 12
- 229910021529 ammonia Inorganic materials 0.000 description 12
- 238000013016 damping Methods 0.000 description 12
- 239000012530 fluid Substances 0.000 description 12
- 238000005470 impregnation Methods 0.000 description 12
- 230000000176 photostabilization Effects 0.000 description 12
- 239000011435 rock Substances 0.000 description 12
- 239000001632 sodium acetate Substances 0.000 description 12
- 229960004249 sodium acetate Drugs 0.000 description 12
- 235000017281 sodium acetate Nutrition 0.000 description 12
- 238000010792 warming Methods 0.000 description 12
- 238000009941 weaving Methods 0.000 description 12
- QPILZZVXGUNELN-UHFFFAOYSA-M sodium;4-amino-5-hydroxynaphthalene-2,7-disulfonate;hydron Chemical compound [Na+].OS(=O)(=O)C1=CC(O)=C2C(N)=CC(S([O-])(=O)=O)=CC2=C1 QPILZZVXGUNELN-UHFFFAOYSA-M 0.000 description 10
- ZSBCZEFDYNLRQQ-UHFFFAOYSA-N 2,4-diaminobenzenesulfonic acid;sodium Chemical compound [Na].NC1=CC=C(S(O)(=O)=O)C(N)=C1 ZSBCZEFDYNLRQQ-UHFFFAOYSA-N 0.000 description 2
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 2
- 239000002657 fibrous material Substances 0.000 description 2
- SQYUJKVKVFILNB-UHFFFAOYSA-N methyl 2-amino-4-[(2,5-dichlorophenyl)carbamoyl]benzoate Chemical compound C1=C(N)C(C(=O)OC)=CC=C1C(=O)NC1=CC(Cl)=CC=C1Cl SQYUJKVKVFILNB-UHFFFAOYSA-N 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 description 1
- 102000011759 adducin Human genes 0.000 description 1
- 108010076723 adducin Proteins 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- BEHLMOQXOSLGHN-UHFFFAOYSA-N benzenamine sulfate Chemical compound OS(=O)(=O)NC1=CC=CC=C1 BEHLMOQXOSLGHN-UHFFFAOYSA-N 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- LTSWGLIYXJGSGL-UHFFFAOYSA-N n-bromoprop-2-enamide Chemical group BrNC(=O)C=C LTSWGLIYXJGSGL-UHFFFAOYSA-N 0.000 description 1
- 238000004045 reactive dyeing Methods 0.000 description 1
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Abstract
The invention provides a yellow reactive dye for wool, which is characterized by having the general structure shown in the specification, wherein R is one of the formulas shown in the specification. The dye has high fixation rate, high fiber-dye bond stability, high solubility, bright and beautiful color light, good color fastness to sunlight and washing fastness, and the parts of the dye, which are not fixed with the fiber, are easy to wash away. The dye contains bromoacrylamide groups, has high reactivity with wool in combination with a leveling agent Sibagol B under the condition of weak acid and high color fixation rate and is suitable for the high fastness requirement of machine washable of International Wool Secretariat.
Description
Technical field
The present invention relates to dye field, particularly a kind of Yellow reactive dye for wool and preparation method thereof and purposes.
Background technology
In recent years, the application of reactive dyeing causes that the requirement to dyestuff quality and practicality constantly increases.Therefore need to continue the new reactive dyestuffs that improve performance that have.With regard to dyeing, the reactive dyestuffs that need now to have suitable affinity and can show the good easy flush away characteristic of non-fixing part simultaneously.In addition, they should demonstrate higher reactivity, good tinctorial yield and have high reactivity, especially should produce the dyeing with high degree of fixation.But existing dyestuff all can not satisfy these requirements from above-mentioned aspect.
Therefore, need a kind of improvement reactive dyestuffs of new wool fiber material, this dyestuff should have high fixation rate, high fiber-dye bond stability, high-dissolvability and very bright-coloured beautiful coloured light.And not with the easy flush away of the part of fiber set.In addition, they should have good light fastness and washing fastness performance.
Summary of the invention
The object of the invention provides a kind of Yellow reactive dye for wool and preparation method thereof and purposes, to solve the deficiencies in the prior art.
Yellow reactive dye for wool of the present invention is a kind of improvement reactive dyestuffs of new wool fiber material, and this dyestuff should have high fixation rate, high fiber-dye bond stability, high-dissolvability and very bright-coloured beautiful coloured light.And not with the easy flush away of the part of fiber set.In addition, it also has good light fastness and washing fastness performance.Its making method is comparatively simple.Dyestuff of the present invention has bromo acrylamide group, cooperates levelling agent Sai Baige B (Sibagol B) and wool that hyperergy is arranged under little sour condition, and degree of fixation is high, meets the high fastness requirement of International Wool Secretariat's " Machine Washable ".
Yellow reactive dye for wool of the present invention has following general structure:
Wherein, R is a kind of in the following formula:
M represents basic metal, comprises Na, K.
Preferably M is Na.This moment, described Yellow reactive dye for wool structural formula can be formula (1):
Described Yellow reactive dye for wool structural formula can also be formula (2):
Described Yellow reactive dye for wool structural formula can also be formula (3):
Described Yellow reactive dye for wool structural formula can also be formula (4):
The preparation method of Yellow reactive dye for wool of the present invention comprises the steps:
A, a diazotization reaction
1. put end water in a doazo reaction pot, (adjacent,, to) the aniline sulfonic acid making beating 1 hour that drops into 100% on the rocksly is cooled to T=10-15 ℃, again to wherein dropping into 100% hydrochloric acid, and holding temperature T=10-15 ℃, stirring reaction 1 hour.
2. on the rocksly in the above-mentioned reactor be cooled to T=0-5 ℃, drop into 100% sodium nitrite solution with 1.5 hours, control temperature T=0-5 ℃, keep and reacted 1 hour.
3. in above-mentioned reactor, drop into the unnecessary Sodium Nitrite of an amount of thionamic acid elimination, process control temp T=0-5 ℃.Aobvious colourless when potassium iodide starch paper, congo-red test paper shows blue look, and then terminal point arrives, and gets diazo liquid.
B, a coupled reaction
1. in a coupled reaction pot, put end water, drop into 100% intermediate R making beating, be stirred to material and dissolve fully.
2. with 30 minutes intermediate R solution joined in the diazo liquid that 3. step a make and react, process control temp T=10-15 ℃, stirring reaction 4-6 hour, holding temperature T=10-15 ℃.It is colourless with fresh H acid solution detection through saltouing to get a little coupling solution, and then terminal point arrives, and gets coupling solution one time.
C, condensation reaction
1. in the condensation reaction pot, put end water, 2 of input 100%, the making beating of 4-diamino benzene sulfonic acid sodium is stirred to material and dissolves fully.
2. on the rocksly in the above-mentioned condensation reaction pot be cooled to T=0-5 ℃, added 100%2,3-propylene bromide acyl chlorides with 1 hour and react, process control temp T=0-5 ℃, stirring reaction 1 hour.With silicon plate layer chromatography method endpoint detection, only there is principal spot on the chromatoplate, without secondary spot, then terminal point arrives, and gets condensated liquid.
D, secondary doazo reaction
1. 100% hydrochloric acid is joined in the condensated liquid that 2. step c make and react, process control temp T=0-5 ℃, stirring reaction 1 hour.
2. add sodium nitrite solution in the above-mentioned reactor with 30 minutes and react, process control temp T=0-5 ℃, keep reaction 1 hour.
3. eliminate unnecessary Sodium Nitrite to wherein dropping into an amount of thionamic acid again, process control temp T=0-5 ℃, aobvious colourless when potassium iodide starch paper, congo-red test paper shows blue look, and then terminal point arrives, and gets the secondary diazo liquid.
E, secondary coupled reaction
The secondary diazo liquid that 3. steps d is made joins in the coupled reaction pot among the step b, and process control temp T=10-15 ℃, transfer pH=6.5-7.0 with 20% soda ash solution, control temperature T=10-15 ℃, keep and reacted 4 hours.It is colourless with fresh H acid solution detection through saltouing to get a little coupling solution, and then terminal point arrives, and gets the secondary coupling solution.
F, spraying drying secondary coupling solution get product.
In sum, the invention has the beneficial effects as follows: dyestuff of the present invention has high fixation rate, high fiber-dye bond stability, high-dissolvability and very bright-coloured beautiful coloured light.And not with the easy flush away of the part of fiber set.In addition, also has excellent comprehensive characteristic, for example: have good light fastness and washing fastness performance.Dyestuff of the present invention meets the high fastness requirement of International Wool Secretariat's " Machine Washable ".
Embodiment
Below by embodiment the present invention is further explained, following example is that the present invention is made an explanation, and is not that protection scope of the present invention is formed any restriction.
The following embodiment 1-4 of preparation of dyestuff method of the present invention:
Embodiment 1 preparation dyestuff operates by following step:
A, a diazotization reaction
1. in a doazo reaction pot, put 1000 parts in end water, drop into 173 part of 100% ORTHO AMINO PHENOL SULPHONIC making beating 1 hour, on the rocksly be cooled to T=10-15 ℃, again to wherein dropping into 95 part of 100% hydrochloric acid, holding temperature T=10-15 ℃, stirring reaction 1 hour.
2. on the rocksly in the above-mentioned reactor be cooled to T=0-5 ℃, dropped into 76 parts of 100% Sodium Nitrites with 1.5 hours and be mixed with 20% solution, T=0-5 ℃ of control temperature of reaction kept reaction 1 hour.
3. in above-mentioned reactor, add the unnecessary Sodium Nitrite of an amount of thionamic acid elimination, process control temp T=0-5 ℃.Aobvious colourless when potassium iodide starch paper, congo-red test paper shows blue look, and then terminal point arrives, and gets diazo liquid.
B, a coupled reaction
1. put 800 parts in end water in the coupled reaction pot, drop into 210 part 100%2, the making beating of 4-diamino benzene sulfonic acid sodium is stirred to material and dissolves fully.
2. use 30 minutes with 2,4-diamino benzene sulfonic acid sodium solution and join in the diazo liquid that 3. step a make and react, process control temp T=10-15 ℃, stirring reaction 4-6 hour, holding temperature T=10-15 ℃.It is colourless with fresh H acid solution detection through saltouing to get a little coupling solution, and then terminal point arrives, and gets coupling solution one time.
C, condensation reaction
1. put 800 parts in end water in the condensation reaction pot, drop into 210 part 100%2, the making beating of 4-diamino benzene sulfonic acid sodium is stirred to material and dissolves fully.
2. on the rocksly in the above-mentioned reactor be cooled to T=0-5 ℃, add 249 part 100%2 with 1 hour, 3-propylene bromide acyl chlorides reacts, and process control temp T=0-5 ℃, stirring reaction 1 hour.Only there is principal spot in silicon plate layer chromatography method endpoint detection on the chromatoplate, without secondary spot, then terminal point arrives, and gets condensated liquid.
D, secondary doazo reaction
1. 95 part of 100% hydrochloric acid is joined in the condensated liquid that 2. step c make and react, process control temp T=0-5 ℃, stirring reaction 1 hour.
2. add 76 parts of sodium nitrite solutions in the above-mentioned reactor with 30 minutes and react, process control temp T=0-5 ℃, keep reaction 1 hour.
3. eliminate unnecessary Sodium Nitrite to wherein dropping into an amount of thionamic acid again, process control temp T=0-5 ℃, aobvious colourless when potassium iodide starch paper, congo-red test paper shows blue look, and then terminal point arrives, and gets the secondary diazo liquid.
E, secondary coupled reaction
The secondary diazo liquid that 3. steps d is made joins in the coupled reaction pot among the step b, and process control temp T=10-15 ℃, transfer pH=6.5-7.0 with 20% soda ash solution, control temperature T=10-15 ℃, keep and reacted 4 hours.It is colourless with fresh H acid solution detection through saltouing to get a little coupling solution, and then terminal point arrives, and gets the secondary coupling solution.
F, spraying drying secondary coupling solution get product.
According to embodiment 1 described method, prepared dye structure formula is suc as formula (1):
Embodiment 2 preparation dyestuffs operate by following step:
A, a diazotization reaction
1. in a doazo reaction pot, put 1000 parts in end water, drop into 216 part of 100% m-sulfanilic acid making beating 1 hour, on the rocksly be cooled to T=10-15 ℃, again to wherein dropping into 119 part of 100% hydrochloric acid, holding temperature T=10-15 ℃, stirring reaction 1 hour.
2. on the rocksly in the above-mentioned reactor be cooled to T=0-5 ℃, dropped into 95 parts of 100% Sodium Nitrites with 1.5 hours and be mixed with 20% solution, T=0-5 ℃ of control temperature of reaction kept reaction 1 hour.
3. in above-mentioned reactor, add the unnecessary Sodium Nitrite of an amount of thionamic acid elimination, process control temp T=0-5 ℃.Aobvious colourless when potassium iodide starch paper, congo-red test paper shows blue look, and then terminal point arrives, and gets diazo liquid.
B, a coupled reaction
1. put 800 parts in end water in the coupled reaction pot, drop into 263 part 100%2, the making beating of 4-diamino benzene sulfonic acid sodium is stirred to material and dissolves fully.
2. use 30 minutes with 2,4-diamino benzene sulfonic acid sodium solution and join in the diazo liquid that 3. step a make and react, process control temp T=10-15 ℃, stirring reaction 4-6 hour, holding temperature T=10-15 ℃.It is colourless with fresh H acid solution detection through saltouing to get a little coupling solution, and then terminal point arrives, and gets coupling solution one time.
C, condensation reaction
1. put 800 parts in end water in the condensation reaction pot, drop into 263 part 100%2, the making beating of 4-diamino benzene sulfonic acid sodium is stirred to material and dissolves fully.
2. on the rocksly in the above-mentioned reactor be cooled to T=0-5 ℃, add 311 part 100%2 with 1 hour, 3-propylene bromide acyl chlorides reacts, and process control temp T=0-5 ℃, stirring reaction 1 hour.Only there is principal spot in silicon plate layer chromatography method endpoint detection on the chromatoplate, without secondary spot, then terminal point arrives, and gets condensated liquid.
D, secondary doazo reaction
1. 119 part of 100% hydrochloric acid is joined in the condensated liquid that 2. step c make and react, process control temp T=0-5 ℃, stirring reaction 1 hour.
2. add 95 parts of sodium nitrite solutions in the above-mentioned reactor with 30 minutes and react, process control temp T=0-5 ℃, keep reaction 1 hour.
3. eliminate unnecessary Sodium Nitrite to wherein dropping into an amount of thionamic acid again, process control temp T=0-5 ℃, aobvious colourless when potassium iodide starch paper, congo-red test paper shows blue look, and then terminal point arrives, and gets the secondary diazo liquid.
E, secondary coupled reaction
The secondary diazo liquid that 3. steps d is made joins in the coupled reaction pot among the step b, and process control temp T=10-15 ℃, transfer pH=6.5-7.0 with 20% soda ash solution, control temperature T=10-15 ℃, keep and reacted 4 hours.It is colourless with fresh H acid solution detection through saltouing to get a little coupling solution, and then terminal point arrives, and gets the secondary coupling solution.
F, spraying drying secondary coupling solution get product.
According to embodiment 2 described methods, prepared dye structure formula is suc as formula (2):
Embodiment 3 preparation dyestuffs operate by following step:
A, a diazotization reaction
1. in a doazo reaction pot, put 1000 parts in end water, drop into 260 part of 100% Sulphanilic Acid making beating 1 hour, on the rocksly be cooled to T=10-15 ℃, again to wherein dropping into 142 part of 100% hydrochloric acid, holding temperature T=10-15 ℃, stirring reaction 1 hour.
2. on the rocksly in the above-mentioned reactor be cooled to T=0-5 ℃, dropped into 114 parts of 100% Sodium Nitrites with 1.5 hours and be mixed with 20% solution, T=0-5 ℃ of control temperature of reaction kept reaction 1 hour.
3. in above-mentioned reactor, add the unnecessary Sodium Nitrite of an amount of thionamic acid elimination, process control temp T=0-5 ℃.Aobvious colourless when potassium iodide starch paper, congo-red test paper shows blue look, and then terminal point arrives, and gets the diazonium thing.
B, a coupled reaction
1. put 800 parts in end water in the coupled reaction pot, drop into 413 part of 100% aniline 2, the making beating of 5-disulfonic acid list sodium salt is stirred to material and dissolves fully.
2. use 30 minutes with aniline 2,5-disulfonic acid solution joins in the diazo liquid that 3. step a make and reacts, and process control temp T=10-15 ℃, stirring reaction 4-6 hour, holding temperature T=10-15 ℃.It is colourless with fresh H acid solution detection through saltouing to get a little coupling solution, and then terminal point arrives, and gets coupling solution one time.
C, condensation reaction
1. put 800 parts in end water in the condensation reaction pot, drop into 315 part 100%2, the making beating of 4-diamino benzene sulfonic acid sodium is stirred to material and dissolves fully.
2. on the rocksly in the above-mentioned reactor be cooled to T=0-5 ℃, add 373 part 100%2 with 1 hour, 3-propylene bromide acyl chlorides reacts, and process control temp T=0-5 ℃, stirring reaction 1 hour.Only there is principal spot in silicon plate layer chromatography method endpoint detection on the chromatoplate, without secondary spot, then terminal point arrives, and gets condensated liquid.
D, secondary doazo reaction
1. 142 part of 100% hydrochloric acid is joined in the condensated liquid that 2. step c make and react, process control temp T=0-5 ℃, stirring reaction 1 hour.
2. add 114 parts of sodium nitrite solutions in the above-mentioned reactor with 30 minutes and react, process control temp T=0-5 ℃, keep reaction 1 hour.
3. eliminate unnecessary Sodium Nitrite to wherein dropping into an amount of thionamic acid again, process control temp T=0-5 ℃, aobvious colourless when potassium iodide starch paper, congo-red test paper shows blue look, and then terminal point arrives, and gets the secondary diazo liquid.
E, secondary coupled reaction
The secondary diazo liquid that 3. steps d is made joins in the coupled reaction pot among the step b, and process control temp T=10-15 ℃, transfer pH=6.5-7.0 with 20% soda ash solution, control temperature T=10-15 ℃, keep and reacted 4 hours.It is colourless with fresh H acid solution detection through saltouing to get a little coupling solution, and then terminal point arrives, and gets the secondary coupling solution.
F, spraying drying secondary coupling solution get product.
According to embodiment 3 described methods, prepared dye structure formula is suc as formula (3):
Embodiment 4 preparation dyestuffs operate by following step:
A, a diazotization reaction
1. in a doazo reaction pot, put 1000 parts in end water, drop into 303 part of 100% ORTHO AMINO PHENOL SULPHONIC making beating 1 hour, on the rocksly be cooled to T=10-15 ℃, again to wherein dropping into 166 part of 100% hydrochloric acid, holding temperature T=10-15 ℃, stirring reaction 1 hour.
2. on the rocksly in the above-mentioned reactor be cooled to T=0-5 ℃, dropped into 133 parts of 100% Sodium Nitrites with 1.5 hours and be mixed with 20% solution, T=0-5 ℃ of control temperature of reaction kept reaction 1 hour.
3. in above-mentioned reactor, add the unnecessary Sodium Nitrite of an amount of thionamic acid elimination, process control temp T=0-5 ℃.Aobvious colourless when potassium iodide starch paper, congo-red test paper shows blue look, and then terminal point arrives, and gets the diazonium thing.
B, a coupled reaction
1. put 800 parts in end water in the coupled reaction pot, drop into 481 part of 100% aniline-2, the making beating of 5-disulfonic acid list sodium salt is stirred to material and dissolves fully.
2. use 30 minutes with aniline-2,5-disulfonic acid solution joins in the diazo liquid that 3. step a make and reacts, and process control temp T=10-15 ℃, stirring reaction 4-6 hour, holding temperature T=10-15 ℃.It is colourless with fresh H acid solution detection through saltouing to get a little coupling solution, and then terminal point arrives, and gets coupling solution one time.
C, condensation reaction
1. put 800 parts in end water in the condensation reaction pot, drop into 368 part 100%2, the making beating of 4-diamino benzene sulfonic acid sodium is stirred to material and dissolves fully.
2. on the rocksly in the above-mentioned reactor be cooled to T=0-5 ℃, add 435 part 100%2 with 1 hour, 3-propylene bromide acyl chlorides reacts, and process control temp T=0-5 ℃, stirring reaction 1 hour.Only there is principal spot in silicon plate layer chromatography method endpoint detection on the chromatoplate, without secondary spot, then terminal point arrives, and gets condensated liquid.
D, secondary doazo reaction
1. 166 part of 100% hydrochloric acid is joined in the condensated liquid that 2. step c make and react, process control temp T=0-5 ℃, stirring reaction 1 hour.
2. add 133 parts of sodium nitrite solutions in the above-mentioned reactor with 30 minutes and react, process control temp T=0-5 ℃, keep reaction 1 hour.
3. eliminate unnecessary Sodium Nitrite to wherein dropping into an amount of thionamic acid again, process control temp T=0-5 ℃, aobvious colourless when potassium iodide starch paper, congo-red test paper shows blue look, and then terminal point arrives, and gets the secondary diazo liquid.
E, secondary coupled reaction
The secondary diazo liquid that 3. steps d is made joins in the coupled reaction pot among the step b, and process control temp T=10-15 ℃, transfer pH=6.5-7.0 with 20% soda ash solution, control temperature T=10-15 ℃, keep and reacted 4 hours.It is colourless with fresh H acid solution detection through saltouing to get a little coupling solution, and then terminal point arrives, and gets the secondary coupling solution.
F, spraying drying secondary coupling solution get product.
According to embodiment 4 described methods, prepared dye structure formula is suc as formula (4):
Following examples are the application of dyestuff of the present invention:
Embodiment 5 dyeing:
0.2 part of dyestuff formula (1) is dissolved in 113 parts of water, adds the acetic acid of 5 parts of pH=4.5 and the damping fluid of sodium-acetate, 2.5 parts of A Baige FFA and 4 parts of Sai Baige B.Wool fiber with 5 parts of this solution impregnation.Solution with the submergence wool fiber is warming up to 99 ℃ gradually again, and ceaselessly fully rocks solution, and temperature was kept 1 hour after arriving 99 ℃, added 0.2 part of ammonia soln after 1 hour again, was cooled to 80 ℃, kept 20 minutes again.Then with dyeing washing, and oven dry, obtain bright-coloured beautiful, washing fastness good, photostabilization is good yellow dyeing and weaving thing.
Embodiment 6 dyeing:
0.4 part of dyestuff formula (1) is dissolved in 227 parts of water, adds the acetic acid of 10 parts of pH=4.5 and the damping fluid of sodium-acetate, 5 parts of A Baige FFA and 8 parts of Sai Baige B.Wool fiber with 10 parts of this solution impregnation.Solution with the submergence wool fiber is warming up to 99 ℃ gradually again, and ceaselessly fully rocks solution, and temperature was kept 1 hour after arriving 99 ℃, added 0.3 part of ammonia soln after 1 hour again, was cooled to 80 ℃, kept 20 minutes again.Then with dyeing washing, and oven dry, obtain bright-coloured beautiful, washing fastness good, photostabilization is good yellow dyeing and weaving thing.
Embodiment 7 dyeing:
0.6 part of dyestuff formula (1) is dissolved in 340 parts of water, adds the acetic acid of 15 parts of pH=4.5 and the damping fluid of sodium-acetate, 7.5 parts of A Baige FFA and 12 parts of Sai Baige B.Wool fiber with 15 parts of this solution impregnation.Solution with the submergence wool fiber is warming up to 99 ℃ gradually again, and ceaselessly fully rocks solution, and temperature was kept 1 hour after arriving 99 ℃, added 0.5 part of ammonia soln after 1 hour again, was cooled to 80 ℃, kept 20 minutes again.Then with dyeing washing, and oven dry, obtain bright-coloured beautiful, washing fastness good, photostabilization is good yellow dyeing and weaving thing.
Embodiment 8 dyeing:
0.2 part of dyestuff formula (2) is dissolved in 113 parts of water, adds the acetic acid of 5 parts of pH=4.5 and the damping fluid of sodium-acetate, 2.5 parts of A Baige FFA and 4 parts of Sai Baige B.Wool fiber with 5 parts of this solution impregnation.Solution with the submergence wool fiber is warming up to 99 ℃ gradually again, and ceaselessly fully rocks solution, and temperature was kept 1 hour after arriving 99 ℃, added 0.2 part of ammonia soln after 1 hour again, was cooled to 80 ℃, kept 20 minutes again.Then with dyeing washing, and oven dry, obtain bright-coloured beautiful, washing fastness good, photostabilization is good yellow dyeing and weaving thing.
Embodiment 9 dyeing:
0.4 part of dyestuff formula (2) is dissolved in 227 parts of water, adds the acetic acid of 10 parts of pH=4.5 and the damping fluid of sodium-acetate, 5 parts of A Baige FFA and 8 parts of Sai Baige B.Wool fiber with 10 parts of this solution impregnation.Solution with the submergence wool fiber is warming up to 99 ℃ gradually again, and ceaselessly fully rocks solution, and temperature was kept 1 hour after arriving 99 ℃, added 0.3 part of ammonia soln after 1 hour again, was cooled to 80 ℃, kept 20 minutes again.Then with dyeing washing, and oven dry, obtain bright-coloured beautiful, washing fastness good, photostabilization is good yellow dyeing and weaving thing.
Embodiment 10 dyeing:
0.6 part of dyestuff formula (2) is dissolved in 340 parts of water, adds the acetic acid of 15 parts of pH=4.5 and the damping fluid of sodium-acetate, 7.5 parts of A Baige FFA and 12 parts of Sai Baige B.Wool fiber with 15 parts of this solution impregnation.Solution with the submergence wool fiber is warming up to 99 ℃ gradually again, and ceaselessly fully rocks solution, and temperature was kept 1 hour after arriving 99 ℃, added 0.5 part of ammonia soln after 1 hour again, was cooled to 80 ℃, kept 20 minutes again.Then with dyeing washing, and oven dry, obtain bright-coloured beautiful, washing fastness good, photostabilization is good yellow dyeing and weaving thing.
Embodiment 11 dyeing:
0.2 part of dyestuff formula (3) is dissolved in 113 parts of water, adds the acetic acid of 5 parts of pH=4.5 and the damping fluid of sodium-acetate, 2.5 parts of A Baige FFA and 4 parts of Sai Baige B.Wool fiber with 5 parts of this solution impregnation.Solution with the submergence wool fiber is warming up to 99 ℃ gradually again, and ceaselessly fully rocks solution, and temperature was kept 1 hour after arriving 99 ℃, added 0.2 part of ammonia soln after 1 hour again, was cooled to 80 ℃, kept 20 minutes again.Then with dyeing washing, and oven dry, obtain bright-coloured beautiful, washing fastness good, photostabilization is good yellow dyeing and weaving thing.
Embodiment 12 dyeing:
0.4 part of dyestuff formula (3) is dissolved in 227 parts of water, adds the acetic acid of 10 parts of pH=4.5 and the damping fluid of sodium-acetate, 5 parts of A Baige FFA and 8 parts of Sai Baige B.Wool fiber with 10 parts of this solution impregnation.Solution with the submergence wool fiber is warming up to 99 ℃ gradually again, and ceaselessly fully rocks solution, and temperature was kept 1 hour after arriving 99 ℃, added 0.3 part of ammonia soln after 1 hour again, was cooled to 80 ℃, kept 20 minutes again.Then with dyeing washing, and oven dry, obtain bright-coloured beautiful, washing fastness good, photostabilization is good yellow dyeing and weaving thing.
Embodiment 13 dyeing:
0.6 part of dyestuff formula (3) is dissolved in 340 parts of water, adds the acetic acid of 15 parts of pH=4.5 and the damping fluid of sodium-acetate, 7.5 parts of A Baige FFA and 12 parts of Sai Baige B.Wool fiber with 15 parts of this solution impregnation.Solution with the submergence wool fiber is warming up to 99 ℃ gradually again, and ceaselessly fully rocks solution, and temperature was kept 1 hour after arriving 99 ℃, added 0.5 part of ammonia soln after 1 hour again, was cooled to 80 ℃, kept 20 minutes again.Then with dyeing washing, and oven dry, obtain bright-coloured beautiful, washing fastness good, photostabilization is good yellow dyeing and weaving thing.
Embodiment 14 dyeing:
0.2 part of dyestuff formula (4) is dissolved in 113 parts of water, adds the acetic acid of 5 parts of pH=4.5 and the damping fluid of sodium-acetate, 2.5 parts of A Baige FFA and 4 parts of Sai Baige B.Wool fiber with 5 parts of this solution impregnation.Solution with the submergence wool fiber is warming up to 99 ℃ gradually again, and ceaselessly fully rocks solution, and temperature was kept 1 hour after arriving 99 ℃, added 0.2 part of ammonia soln after 1 hour again, was cooled to 80 ℃, kept 20 minutes again.Then with dyeing washing, and oven dry, obtain bright-coloured beautiful, washing fastness good, photostabilization is good yellow dyeing and weaving thing.
Embodiment 15 dyeing:
0.4 part of dyestuff formula (4) is dissolved in 227 parts of water, adds the acetic acid of 10 parts of pH=4.5 and the damping fluid of sodium-acetate, 5 parts of A Baige FFA and 8 parts of Sai Baige B.Wool fiber with 10 parts of this solution impregnation.Solution with the submergence wool fiber is warming up to 99 ℃ gradually again, and ceaselessly fully rocks solution, and temperature was kept 1 hour after arriving 99 ℃, added 0.3 part of ammonia soln after 1 hour again, was cooled to 80 ℃, kept 20 minutes again.Then with dyeing washing, and oven dry, obtain bright-coloured beautiful, washing fastness good, photostabilization is good yellow dyeing and weaving thing.
Embodiment 16 dyeing:
0.6 part of dyestuff formula (4) is dissolved in 340 parts of water, adds the acetic acid of 15 parts of pH=4.5 and the damping fluid of sodium-acetate, 7.5 parts of A Baige FFA and 12 parts of Sai Baige B.Wool fiber with 15 parts of this solution impregnation.Solution with the submergence wool fiber is warming up to 99 ℃ gradually again, and ceaselessly fully rocks solution, and temperature was kept 1 hour after arriving 99 ℃, added 0.5 part of ammonia soln after 1 hour again, was cooled to 80 ℃, kept 20 minutes again.Then with dyeing washing, and oven dry, obtain bright-coloured beautiful, washing fastness good, photostabilization is good yellow dyeing and weaving thing.
Below be the Yellow reactive dye for wool application performance table that the present invention prepares:
Claims (8)
1. Yellow reactive dye for wool is characterized in that having following general structure:
Wherein, R is a kind of in the following formula:
M represents basic metal, comprises Na, K.
2. Yellow reactive dye for wool according to claim 1 is characterized in that described M is Na.
3. Yellow reactive dye for wool according to claim 2 is characterized in that its structural formula is formula (1):
4. Yellow reactive dye for wool according to claim 2 is characterized in that its structural formula is formula (2):
5. Yellow reactive dye for wool according to claim 2 is characterized in that its structural formula is formula (3):
6. Yellow reactive dye for wool according to claim 2 is characterized in that its structural formula is formula (4):
7. the preparation method of described arbitrary Yellow reactive dye for wool is characterized in that comprising the steps: according to claim 1-6
A, a diazotization reaction
1. in a doazo reaction pot, put end water, drop into 100% neighbour or Sulphanilic Acid making beating 1 hour, on the rocksly be cooled to T=10-15 ℃, again to wherein dropping into hydrochloric acid, holding temperature T=10-15 ℃, stirring reaction 1 hour;
2. on the rocksly in the above-mentioned reactor be cooled to T=0-5 ℃, drop into 20% sodium nitrite solution with 1.5 hours, control temperature T=0-5 ℃, keep and reacted 1 hour;
3. in above-mentioned reactor, drop into the unnecessary Sodium Nitrite of an amount of thionamic acid elimination, process control temp T=0-5 ℃; Aobvious colourless when potassium iodide starch paper, congo-red test paper shows blue look, and then terminal point arrives, and gets diazo liquid;
B, a coupled reaction
1. in the coupled reaction pot, put end water, drop into 100% intermediate R making beating, be stirred to material and dissolve fully;
2. with 30 minutes intermediate R solution joined in the diazo liquid that 3. step a make and react, process control temp T=10-15 ℃, stirring reaction 4-6 hour, holding temperature T=10-15 ℃; It is colourless with fresh H acid solution detection through saltouing to get a little coupling solution, and then terminal point arrives, and gets coupling solution one time;
C, condensation reaction
1. in the condensation reaction pot, put end water, 2 of input 100%, the making beating of 4-diamino benzene sulfonic acid sodium is stirred to material and dissolves fully;
2. on the rocksly in the above-mentioned condensation reaction pot be cooled to T=0-5 ℃, with added in 1 hour 100% 2,3-propylene bromide acyl chlorides reacts, process control temp T=0-5 ℃, stirring reaction 1 hour; With silicon plate layer chromatography method endpoint detection, only there is principal spot on the chromatoplate, without secondary spot, then terminal point arrives, and gets condensated liquid;
D, secondary doazo reaction
1. hydrochloric acid is joined in the condensated liquid that 2. step c make and react, process control temp T=0-5 ℃, stirring reaction 1 hour;
2. add sodium nitrite solution in the above-mentioned reactor with 30 minutes and react, process control temp T=0-5 ℃, keep reaction 1 hour;
3. eliminate unnecessary Sodium Nitrite, process control temp T=0-5 ℃ to wherein dropping into an amount of thionamic acid again; Aobvious colourless when potassium iodide starch paper, congo-red test paper shows blue look, and then terminal point arrives, and gets the secondary diazo liquid;
E, secondary coupled reaction
The secondary diazo liquid that 3. steps d is made joins in the coupled reaction pot among the step b, and process control temp T=10-15 ℃, transfer pH=6.5-7.0 with 20% soda ash solution, control temperature T=10-15 ℃, keep and reacted 4 hours; It is colourless with fresh H acid solution detection through saltouing to get a little coupling solution, and then terminal point arrives, and gets the secondary coupling solution;
F, this secondary coupling solution of spraying drying get product.
8. the purposes of described arbitrary Yellow reactive dye for wool according to claim 1-6, it is characterized in that: described Yellow reactive dye for wool is applicable to the dyeing of wool fiber.
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