CN104262998A - Red reactive dye for dyeing at normal-moderate temperature and compound mixture thereof - Google Patents
Red reactive dye for dyeing at normal-moderate temperature and compound mixture thereof Download PDFInfo
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- CN104262998A CN104262998A CN201410446326.7A CN201410446326A CN104262998A CN 104262998 A CN104262998 A CN 104262998A CN 201410446326 A CN201410446326 A CN 201410446326A CN 104262998 A CN104262998 A CN 104262998A
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- 239000000985 reactive dye Substances 0.000 title claims abstract description 39
- 239000000203 mixture Substances 0.000 title claims abstract description 27
- 150000001875 compounds Chemical class 0.000 title claims abstract description 7
- 238000004043 dyeing Methods 0.000 title abstract description 19
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims abstract description 13
- 239000002131 composite material Substances 0.000 claims description 17
- 238000000034 method Methods 0.000 abstract description 11
- 230000000694 effects Effects 0.000 abstract description 3
- 238000009979 jig dyeing Methods 0.000 abstract 1
- 239000000975 dye Substances 0.000 description 31
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000005859 coupling reaction Methods 0.000 description 9
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical class [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 9
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 230000008878 coupling Effects 0.000 description 8
- 238000010168 coupling process Methods 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 229920000742 Cotton Polymers 0.000 description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 238000005097 cold rolling Methods 0.000 description 6
- -1 β-ethyl sulfone sulfuric acid ester Chemical class 0.000 description 6
- 235000010288 sodium nitrite Nutrition 0.000 description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- POJOORKDYOPQLS-UHFFFAOYSA-L barium(2+) 5-chloro-2-[(2-hydroxynaphthalen-1-yl)diazenyl]-4-methylbenzenesulfonate Chemical compound [Ba+2].C1=C(Cl)C(C)=CC(N=NC=2C3=CC=CC=C3C=CC=2O)=C1S([O-])(=O)=O.C1=C(Cl)C(C)=CC(N=NC=2C3=CC=CC=C3C=CC=2O)=C1S([O-])(=O)=O POJOORKDYOPQLS-UHFFFAOYSA-L 0.000 description 4
- 239000004202 carbamide Substances 0.000 description 4
- 235000019800 disodium phosphate Nutrition 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- 229940045641 monobasic sodium phosphate Drugs 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 239000012752 auxiliary agent Substances 0.000 description 3
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 3
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 3
- 229910000397 disodium phosphate Inorganic materials 0.000 description 3
- 239000012065 filter cake Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 235000017550 sodium carbonate Nutrition 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- JVMSQRAXNZPDHF-UHFFFAOYSA-N 2,4-diaminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C(N)=C1 JVMSQRAXNZPDHF-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000001989 diazonium salts Chemical class 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- OMRXVBREYFZQHU-UHFFFAOYSA-N 2,4-dichloro-1,3,5-triazine Chemical compound ClC1=NC=NC(Cl)=N1 OMRXVBREYFZQHU-UHFFFAOYSA-N 0.000 description 1
- 101100118680 Caenorhabditis elegans sec-61.G gene Proteins 0.000 description 1
- FMLLIIRGEODHGZ-UHFFFAOYSA-N S(=O)(=O)(O)O.NCCS(=O)(=O)CCN Chemical compound S(=O)(=O)(O)O.NCCS(=O)(=O)CCN FMLLIIRGEODHGZ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- CYGKLLHTPPFPHH-UHFFFAOYSA-N aniline;hydrate Chemical compound O.NC1=CC=CC=C1 CYGKLLHTPPFPHH-UHFFFAOYSA-N 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 238000010009 beating Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- ONTQJDKFANPPKK-UHFFFAOYSA-L chembl3185981 Chemical compound [Na+].[Na+].CC1=CC(C)=C(S([O-])(=O)=O)C=C1N=NC1=CC(S([O-])(=O)=O)=C(C=CC=C2)C2=C1O ONTQJDKFANPPKK-UHFFFAOYSA-L 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- XWZDJOJCYUSIEY-UHFFFAOYSA-L disodium 5-[(4,6-dichloro-1,3,5-triazin-2-yl)amino]-4-hydroxy-3-phenyldiazenylnaphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].Oc1c(N=Nc2ccccc2)c(cc2cc(cc(Nc3nc(Cl)nc(Cl)n3)c12)S([O-])(=O)=O)S([O-])(=O)=O XWZDJOJCYUSIEY-UHFFFAOYSA-L 0.000 description 1
- 238000004134 energy conservation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000009980 pad dyeing Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 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 1
- 239000000243 solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
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Abstract
The invention provides a red reactive dye for dyeing at normal-moderate temperature and a compound mixture thereof. The structural general formula (I) of the reactive dye is disclosed in the specification. The reactive dye is one in the structural general formula, wherein R1 is H or SO3Na, R2 is H or SO3Na, and the group SO2C2H4OSO3Na is in contraposition or meta-position of diazo group. The invention also provides a reactive dye compound mixture which comprises the red reactive dye, reactive yellow A and reactive blue B. The red reactive dye for dyeing at normal-moderate temperature and compound mixture thereof have excellent dyeing effect at normal-moderate temperature, and are suitable for jig dyeing and cold pad-batch dyeing techniques.
Description
Technical field
The present invention relates to chemical field, the red reactive dyes dyeed under often a kind of-middle temperature and composite mixture thereof.
Background technology
It is cotton that reactive dyestuffs are mainly used in dye, also sticky fiber and silk fiber dyeing is applicable to, bright in colour, chromatogram is complete, fastness is excellent, normally contaminate cotton first-selected dyestuff, because the structure introducing active group is different, dyeing condition and degree of fixation are also different, dissimilar reactive dyestuffs are applicable to different dyeings, the wherein cold rolling batch-dying process of reactive dyestuffs, equipment is simple, fixation under normal temperature, turn improve the degree of fixation of dyestuff simultaneously, compared with other dyeing, obvious energy conservation, improve the utilization ratio of dyestuff, reduce and pollute, minimizing water, can reach economical, efficiently, the object of energy-saving and emission-reduction.The reactive dyestuffs of European and American areas 35% are used for cold rolling batch-dying process, the at present domestic reactive dyestuffs for cold pad--batch, and select in X-type, KN-type, M-type reactive dyestuffs, dye fixing rate is low, rolls rear pilling up time 2-24 hour.Current cold pad--batch adopts dissimilar reactive dyestuffs combination, and degree of fixation is different, and pilling up time is different in size, not yet has ripe supporting dyestuff and auxiliary agent.
Known reactive brilliant red such as activated red X-3B structural formula is:
Reactive red M-2BE (C.I. Reactive Red 194):
X-type reactive dyestuffs containing dichloro s-triazine and the KN reactive dyestuffs containing β-ethyl sulfone sulfuric acid ester, be suitable for dye gigging and the cold rolling batch-dying process of energy-conserving and environment-protective, but X-and KN-type reactive dyestuffs, and only have an active group, degree of fixation is low.Such as reactive brilliant red x-3b, can be used for cold rolling batch-dying process, but degree of fixation is low.In addition, reactive brilliant red M-2BE is middle Resist Reactive Dyes, is not suitable for cold rolling batch-dying process.
Summary of the invention
The red reactive dyes dyeed under the invention provides often a kind of-middle temperature and composite mixture thereof, to solve the problem.
The present invention is achieved in that
The red reactive dyes dyeed under often-middle temperature, its general structure (I) is as follows:
Described red reactive dyes is the one in described general structure; Wherein: R
1h or SO
3na, R
2h or SO
3na, group SO
2c
2h
4oSO
3na is in diazo contraposition or a position.
Preferably, described red reactive dyes is the mixture of the two or more compounds in described general structure.
The application also provides a kind of reactive dyestuffs composite mixture, comprises described red reactive dyes, also comprises A reactive yellow and B Reactive blue, and the general structure of described A reactive yellow and described B Reactive blue is as follows respectively:
A reactive yellow
Wherein group SO
2c
2h
4oSO
3na is in diazo contraposition or a position;
B Reactive blue
Wherein, R
3for H or SO
3na, R
4for H or SO
3na;
Described red reactive dyes, described A reactive yellow, described B Reactive blue in the mass percent of the composite mixture of described reactive dyestuffs are: described red reactive dyes 12-42%, described A reactive yellow 26-40%, described B Reactive blue 20-60%.
The red reactive dyes dyeed under normal-middle temperature using the application to provide and composite mixture thereof, can bring following beneficial effect:
The first, provide new, that degree of fixation is high red reactive dyes; Second provides the composite mixture of new reactive dyestuffs; 3rd, the dyestuff of the double-active group provided, is applicable to middle low temperature dyeing, for the cold pad--batch dye dyeing of cotton fabric provides new selection, and can energy-saving and emission-reduction.
Embodiment
Below in conjunction with embodiment, the application is described in further detail.Be understandable that, specific embodiment described herein is only for explaining the application, but not the restriction to the application.
The red reactive dyes dyeed under often-middle temperature, its general structure (I) is as follows:
Described red reactive dyes is the one in described general structure; Wherein: R
1h or SO
3na, R
2h or SO
3na, group SO
2c
2h
4oSO
3na is in diazo contraposition or a position.
Preferably, described red reactive dyes is the mixture of the two or more compounds in described general structure.
The application also provides a kind of reactive dyestuffs composite mixture, comprises described red reactive dyes, also comprises A reactive yellow and B Reactive blue, and the general structure of described A reactive yellow and described B Reactive blue is as follows respectively:
A reactive yellow
Wherein group SO
2c
2h
4oSO
3na is in diazo contraposition or a position;
B Reactive blue
Wherein, R
3for H or SO
3na, R
4for H or SO
3na;
Described red reactive dyes, described A reactive yellow, described B Reactive blue in the mass percent of the composite mixture of described reactive dyestuffs are: described red reactive dyes 12-42%, described A reactive yellow 26-40%, described B Reactive blue 20-60%.
Embodiment 1
Prepare red reactive dyes structural formula as follows:
The cyanuric chloride adding 70mL frozen water and 9.8 gram 98% in there-necked flask is pulled an oar 1 hour, drip containing 17.2 grams of H aqueous acids at 0-5 DEG C, and thread adds the reaction of soda ash aqueous solution adjustment maintenance subacidity, finishes, within about 2 hours, obtained coupling component treats coupling to insulation reaction to terminal.
100 grams of frozen water are added in there-necked flask, then 14.5 grams of hydrochloric acid to amino-ethyl sulfone sulfate base aniline-water solution and 16 gram 30% are slowly added, ice bath stirs 20 minutes, control the aqueous solution of less than 2 DEG C instillations containing 3.6 grams of Sodium Nitrites, 0-5 DEG C of reaction 1 hour, add 0.5 gram of thionamic acid, cancellation residue Sodium Nitrite, obtains diazo liquid.
Diazo liquid is added in coupling component above, stirring reaction at 8 DEG C, and the PH=6.5-7 of reactant is regulated with soda ash liquid, 5-8 DEG C of reaction 4 hours, add urea and react 1-11 hour again, add sodium chloride salt and analyse, filter, dyestuff filter-cakes and 6 grams of Sodium phosphate dibasics and SODIUM PHOSPHATE, MONOBASIC mixed solution are adjusted all, 80-85 DEG C of oven dry, obtain red reactive dyes.
It is pointed out that reactive yellow M-3RE, reactive brilliant red M-2BE and Reactive blue M-2GE are three primary colors, be the representative works of M type reactive dyestuffs, degree of fixation is high, widely uses both at home and abroad.Therefore, the application selects reactive brilliant red M-2BE as main comparison dyestuff, so that the performance of the red reactive dyes that the application provides to be described.
The dyestuff existing reactive dyestuffs and embodiment 1 prepared dyes respectively by X-method and M-method respectively, contrasts its degree of fixation, obtains result as shown in table 1.
Degree of fixation (%) comparison sheet of table 1 different activities base reactive dyestuffs coloured differently method
Note 1 data take from " application handbook " volume two;
Note 2 data take from report data;
Note 3 Inspection Unit: national dyestuff Quality Supervision and Inspection Center.
Red reactive dyes M-2BE is carried out dyefastness with the reactive dyestuffs of embodiment 1 gained compare, obtain result as shown in table 2 below.
Table 2 dyeing fastness comparison sheet
Embodiment 2-4
Can obtain other several red reactive dyes according to aforesaid method, its result is as shown in table 3 below.
Table 3 embodiment 2-4 dyestuff
| Embodiment | β-ethyl sulfone sulfuric acid ester | R 1 | R 2 | Color |
| 2 | Between position | SO 3Na | H | Red |
| 3 | Contraposition | H | SO 3Na | Red |
| 4 | Between position | H | SO 3Na | Red |
Embodiment 5-6
Choose the formula I dyestuff that A reactive yellow, B Reactive blue and the application provide according to a certain percentage, fully mixing obtains the composite mixture of dyestuff, shown in table 4 specific as follows:
The concrete composition of table 4 embodiment 5-6
Note: the massfraction (mass percent) of data shared by each component in table.
It is important to note that the preparation method of A reactive yellow is roughly as follows:
1. water, to ethyl sulfonyl sulfate base aniline or ethyl sulfonyl sulfate base aniline, hydrochloric acid reaction, then add Sodium Nitrite and thionamic acid, obtain diazo liquid;
2. add 2,4-diamino benzene sulfonic acid in water, then add after above-mentioned diazo liquid carries out coupled reaction adjust ph and continue reaction acquisition coupling product;
3. add in above-mentioned coupling product after cyanuric chloride and frozen water mixing making beating, add urea, carry out saltouing, filtering after having reacted, filter cake and Sodium phosphate dibasic and SODIUM PHOSPHATE, MONOBASIC mixed solution are mixed well, are dried, and obtain described A reactive yellow.
The preparation method of B Reactive blue is roughly as follows:
1. water, to ethyl sulfonyl sulfate base aniline or ethyl sulfonyl sulfate base aniline, hydrochloric acid reaction, then add Sodium Nitrite and thionamic acid, obtain diazo liquid; Added in H acid by above-mentioned diazo liquid and carry out coupling, regulate pH, reaction obtains coupling product;
2. cyanuric chloride and frozen water mixing, add 2,4-diamino benzene sulfonic acid, hydrochloric acid, then add Sodium Nitrite, be obtained by reacting diazonium compound;
3. diazonium compound described in joins in described coupling product, adds urea, saltouts, filters after having reacted, and filter cake and Sodium phosphate dibasic and SODIUM PHOSPHATE, MONOBASIC are mixed well, dried, and obtain described B reactive blue dye.
In addition, reactive dyestuffs the application provided and X-type or KN-type or M-type dye or other dyestuffs mix, and add auxiliary agent, also can obtain the composite mixture of reactive dyestuffs.Wherein auxiliary agent can be the sodium salts such as sodium sulfate, Sodium phosphate dibasic, SODIUM PHOSPHATE, MONOBASIC.
Red reactive dyes provided by the invention and composite mixture thereof, be mainly used in dye cotton, be also applicable to the dyeing of the fibers such as sticky fiber and silk, this series dyes has double-active group, be applicable to middle low temperature dyeing, obtain color depth dense, bright in colour, fastness is excellent, can with X-type, KN-type and M-type dye collocation uses, and especially dyes under normal temperature, there is excellent effect, be applicable to dye gigging and cold rolling batch-dying process.
Therefore, the application also provides the application of a kind of described reactive dyestuffs or the composite mixture of described reactive dyestuffs, is applied to the middle gentle low temperature dyeing of cotton fabric, especially cotton fabric cold pad--batch dye dyeing.
Reactive dyestuffs cold pad--batch dye dyeing shown in embodiment 1 is contaminated textile plain, shown in its dye liquor table 5 composed as follows.
Table 5 cold pad--batch dye dye liquor composition
| Dye liquid component | Consumption |
| Embodiment 1 dyestuff | 20g/L |
| Urea | 60g/L |
| Soda ash | 15g/L |
Its concrete technology parameter is: pad dyeing temperature 27 DEG C, and bank up time 6Hrs.Soap after having dyeed, soaping condition is: neutral soap flakes 3g/L, bath raio 1:100, boils and boils 15 minutes, then fully wash, dry.
Detecting and obtaining its degree of fixation is 74.81%.
The red reactive dyes using the application to provide and composite mixture thereof, provide new, that degree of fixation is high reactive dyestuffs and the composite mixture of reactive dyestuffs; Be applicable to middle low temperature dyeing, for the cold pad--batch dye dyeing of cotton fabric provides new selection, can energy-saving and emission-reduction.
The foregoing is only the preferred embodiment of the application, be not limited to the application, for a person skilled in the art, the application can have various modifications and variations.Within all spirit in the application and principle, any amendment done, equivalent replacement, improvement etc., within the protection domain that all should be included in the application.
Claims (3)
1. the red reactive dyes dyeed under normal-middle temperature, its general structure (I) is as follows:
It is characterized in that, described red reactive dyes is the one in described general structure;
Wherein: R
1h or SO
3na, R
2h or SO
3na, group SO
2c
2h
4oSO
3na is in diazo contraposition or a position.
2. red reactive dyes according to claim 1, wherein, described red reactive dyes is the mixture of the two or more compounds in described general structure.
3. the composite mixture of reactive dyestuffs, comprises the red reactive dyes described in claim 1 or 2, it is characterized in that, also comprises A reactive yellow and B Reactive blue, and the general structure of described A reactive yellow and described B Reactive blue is as follows respectively:
A reactive yellow
Wherein group SO
2c
2h
4oSO
3na is in diazo contraposition or a position;
B Reactive blue
Wherein, R
3for H or SO
3na, R
4for H or SO
3na;
Described red reactive dyes, described A reactive yellow, described B Reactive blue in the mass percent of the composite mixture of described reactive dyestuffs are: described red reactive dyes 12-42%, described A reactive yellow 26-40%, described B Reactive blue 20-60%.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410446326.7A CN104262998B (en) | 2014-09-03 | 2014-09-03 | The red reactive dyes dyeed under often-middle temperature and composite mixture thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410446326.7A CN104262998B (en) | 2014-09-03 | 2014-09-03 | The red reactive dyes dyeed under often-middle temperature and composite mixture thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN104262998A true CN104262998A (en) | 2015-01-07 |
| CN104262998B CN104262998B (en) | 2015-09-30 |
Family
ID=52154589
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
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Country Status (1)
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1221360A (en) * | 1982-05-12 | 1987-05-05 | Hans-Joachim Bredereck | Monoazo compounds, processes for their preparation, and their use as dyestuffs |
| WO1995021893A1 (en) * | 1994-02-10 | 1995-08-17 | Zeneca Limited | Azo dyes |
| CN1145935A (en) * | 1995-03-24 | 1997-03-26 | Basf公司 | Reactive dyes with benzo-fused heterocycle as anchor |
| CN1477159A (en) * | 2002-07-10 | 2004-02-25 | ����־��˹���֯Ʒ��Ⱦ�����Ϲ�˾ | Fibre reactivity azo-dye |
-
2014
- 2014-09-03 CN CN201410446326.7A patent/CN104262998B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1221360A (en) * | 1982-05-12 | 1987-05-05 | Hans-Joachim Bredereck | Monoazo compounds, processes for their preparation, and their use as dyestuffs |
| WO1995021893A1 (en) * | 1994-02-10 | 1995-08-17 | Zeneca Limited | Azo dyes |
| CN1145935A (en) * | 1995-03-24 | 1997-03-26 | Basf公司 | Reactive dyes with benzo-fused heterocycle as anchor |
| CN1477159A (en) * | 2002-07-10 | 2004-02-25 | ����־��˹���֯Ʒ��Ⱦ�����Ϲ�˾ | Fibre reactivity azo-dye |
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Denomination of invention: Red reactive dyes dyed at normal medium temperature and their compound mixtures Effective date of registration: 20211020 Granted publication date: 20150930 Pledgee: Yantai boster Pigment Co.,Ltd. Pledgor: PENGLAI JIAXIN DYES & CHEMICAL Co.,Ltd. Registration number: Y2021980010990 |
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Date of cancellation: 20221115 Granted publication date: 20150930 Pledgee: Yantai boster Pigment Co.,Ltd. Pledgor: PENGLAI JIAXIN DYES & CHEMICAL Co.,Ltd. Registration number: Y2021980010990 |
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Denomination of invention: Red reactive dyes and their mixtures dyed at normal-medium temperature Effective date of registration: 20230129 Granted publication date: 20150930 Pledgee: Yantai Yida Financial Leasing Co.,Ltd. Pledgor: PENGLAI JIAXIN DYES & CHEMICAL Co.,Ltd. Registration number: Y2023980031636 |
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