CN106398301A - Reactive yellow dye compound containing fluorine and chlorine elements and preparation method of compound - Google Patents
Reactive yellow dye compound containing fluorine and chlorine elements and preparation method of compound Download PDFInfo
- Publication number
- CN106398301A CN106398301A CN201610770892.2A CN201610770892A CN106398301A CN 106398301 A CN106398301 A CN 106398301A CN 201610770892 A CN201610770892 A CN 201610770892A CN 106398301 A CN106398301 A CN 106398301A
- Authority
- CN
- China
- Prior art keywords
- reactive yellow
- yellow dye
- fluorine
- preparation
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Classifications
-
- 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
-
- 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
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/58—Material containing hydroxyl groups
- D06P3/60—Natural or regenerated cellulose
- D06P3/66—Natural or regenerated cellulose using reactive dyes
- D06P3/666—Natural or regenerated cellulose using reactive dyes reactive group not directly attached to heterocyclic group
Abstract
The invention discloses a reactive yellow dye compound containing fluorine and chlorine elements and a preparation method of the compound. Two fluorine atoms in the compound have higher activity, can be regarded as dual-active-group dye and have higher fixation rate, and the dye contains four active groups and has good color fastness.
Description
Technical field
The present invention relates to active dye technical field, especially relate to the reactive yellow containing fluorine, chlorine element in a kind of structure
Dye composition and preparation method thereof.
Background technology
Reactive dye are so that its chromatograph is complete, bright-colored, function admirable, strong applicability the advantages of and developed rapidly.
Because current China is further strict for the protection of environment, advocating energetically being capable of energy-saving and emission-reduction, eco-friendly friendly process.Right
COD in different dyeings produces for the reactive dye wastewater flow rate and waste water is very different, for contaminating dye
Due to the requirement of bath raio for color, this kind of dyeing will produce substantial amounts of waste water, and the utilization rate of exhaust dyeing technique dyestuff
The dyestuff of also not high (general double-active radical dye degree of fixation 60～80%) a large amount of non-fixation is present in waste water so that in waste water
COD have height, the dyestuff using high colour-fast rate is one of the effective way reducing dyeing waste water.
The effective way improving dye fixing rate is to increase the active group quantity of dyestuff, but active group can increase dyestuff too much
Substantivity, the application performance of impact dyestuff, such as level-dyeing property, viscous color fastness etc., domestic usual method is to live different
Property base is connected on same dye matrix (dyestuff such as domestic ME type, Type B) increases consolidating of dyestuff by the complementation of active group
Color rate.But this kind of method due to the activity of active group do not match so that the increased amplitude of the degree of fixation of dyestuff less, general only
70～80%.So improving degree of fixation or the task of top priority of dyestuff.
Content of the invention
The problems referred to above existing for prior art, the applicant provides a kind of fluorine-containing, chlorine element Yellow reactive dyes
Compound and preparation method thereof.Two fluorine atoms in the compounds of this invention have higher activity, are considered as double-active radical
Dyestuff, has compared with high colour-fast rate, this dyestuff contains four active groups, and viscous color fastness is fine.
Technical scheme is as follows：
A kind of fluorine-containing, chlorine element reactive yellow dye compounds, the structural formula of described compound is：
A kind of preparation method of described fluorine-containing, chlorine element reactive yellow dye compounds, the reaction stream of described preparation method
Journey is as follows：
A kind of application of described fluorine-containing, chlorine element reactive yellow dye compounds, by described fluorine-containing, chlorine element reactive yellow
Dye composition is applied to exhaust dyeing, continuous knot dyeing or the printing technology of cellulose base fiber fabric.
Described cellulose base fiber fabric is the cellulosic fibre material of hydroxyl and/or nitrogen.Described cellulose base fiber fabric
For cotton, viscose glue, fiber crops or its blend fabric.
Beneficial the having technical effect that of the present invention：
The present invention is to have been surprisingly found that three fluorine atoms of trifluoropyrimidine active group all have work when studying fluorine-containing active group
Property, can and fiber-reactive, after being connected with parent dye, remaining two fluorine atom activity are also very high, are considered as double activated
Radical dye, it is possible to obtain high colour-fast rate dyestuff, this dyestuff contains four active groups, and the viscous color fastness of this dyestuff is also better than it simultaneously
The dyestuff that he commonly uses, with dye composition of the present invention can apply to the exhaust dyeing of cellulose base fiber fabric, continuous knot dyeing or
Printing technology；Other fastness abilities of dyestuff are excellent.
Specific embodiment
With reference to embodiment, the present invention is specifically described.
Embodiment 1
A kind of described fluorine-containing, chlorine element reactive yellow dye compounds, the preparation method of described compound includes walking as follows
Suddenly：
(1) 21.0 parts of 2,4- diamino benzene sulfonic acid sodium (double between hereinafter referred to as) is dissolved in 200 parts of water, is subsequently adding
18.8 parts of Cyanuric Chloride, under the conditions of 5 DEG C, carries out being condensed 2.0h, is terminal, prepared condensation product when continuously double；
(2) 28.1 parts of para-esters are dissolved in 200 parts of water, add 10% sodium carbonate liquor, adjustment pH is 6, is allowed to entirely molten,
Add in the condensation substance that step (1) is obtained, be warming up to 35 DEG C, carry out two condensations, keep pH to be 5, react 4.0h, pH no longer declines
When be terminal, be obtained two condensation products；
(3) it is subsequently adding 22 part 30% of hydrochloric acid, is cooled to less than 5 DEG C, add 6.9 parts (being previously dissolved in 16 parts of water)
Sodium nitrite carries out diazotising, and temperature is maintained at 3 DEG C, and keeps the micro- excess of nitrous acid, reacts 2.0h, as terminal, weight is obtained
Nitrogen salt；
(4) separately take between 210 parts double be dissolved in 200 parts of water, and add the diazol that step (3) is obtained, the condition being 3 in pH
It is terminal, prepared coupling product during lower coupling reaction 45h, no diazol；
(5) take again between 21.0 parts double be dissolved in 200 parts of water, the trifluoropyrimidine being subsequently adding 13.5 parts is 10 in temperature
DEG C, pH is to be condensed 4.0h under conditions of 5, is terminal, prepared condensation product when continuously double；
(6) add 22 part 30% of hydrochloric acid, be cooled to less than 2 DEG C, add 6.9 parts (being previously dissolved in 16 parts of water) sub-
Sodium nitrate carries out diazotising, and temperature is maintained at 2 DEG C, and keeps the micro- excess of nitrous acid, reacts 2.0h, as terminal, prepared diazonium
Salt；
(7) diazol that step (6) is obtained is added in the coupling product that step (4) is obtained, and is 15 DEG C, pH in temperature
Under conditions of 7, coupling 4.0h again, obtain described compound；Testing its molecular weight by HPLC-MS is 1093, ties with it
Structure is consistent.
Test case：
Take the dye composition that 3 parts of embodiments 1 are obtained, add 6 parts of Matrii Sulfas Exsiccatus, 1 part of soda and water, be made into bath raio 1:15 dyes
Bath, routinely operational approach bafta is carried out at 60 DEG C dye 60min, then neutralization, washing, finally soap, hot water again
Wash, cold water is washed, dry, obtain yellow cotton fabric.Properties of product test result is shown in Table 1.
Table 1
| Sequence number | Staining fastness | Antifriction dries/and wet | Sun-proof | Degree of fixation |
| Embodiment 1 | 4 grades | 4/3 | 5 | 91.9% |
Claims (5)
1. a kind of fluorine-containing, chlorine element reactive yellow dye compounds are it is characterised in that the structural formula of described compound is：
2. a kind of preparation method of fluorine-containing, chlorine element reactive yellow dye compounds described in claim 1 is it is characterised in that described
The reaction process of preparation method is as follows：
3. a kind of application of fluorine-containing, chlorine element reactive yellow dye compounds described in claim 1 is it is characterised in that contain described
Fluorine, the reactive yellow dye compounds of chlorine element are applied to exhaust dyeing, continuous knot dyeing or the printing technology of cellulose base fiber fabric.
4. apply according to claim 3 it is characterised in that described cellulose base fiber fabric is the fiber of hydroxyl and/or nitrogen
Cellulose fiber material.
5. according to claim 4 application it is characterised in that described cellulose base fiber fabric be cotton, viscose glue, fiber crops or its mix
Yarn fabric.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610770892.2A CN106398301A (en) | 2016-08-30 | 2016-08-30 | Reactive yellow dye compound containing fluorine and chlorine elements and preparation method of compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610770892.2A CN106398301A (en) | 2016-08-30 | 2016-08-30 | Reactive yellow dye compound containing fluorine and chlorine elements and preparation method of compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN106398301A true CN106398301A (en) | 2017-02-15 |
Family
ID=58002186
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610770892.2A Pending CN106398301A (en) | 2016-08-30 | 2016-08-30 | Reactive yellow dye compound containing fluorine and chlorine elements and preparation method of compound |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN106398301A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116144195A (en) * | 2022-12-12 | 2023-05-23 | 江苏德美科化工有限公司 | High-performance alkali-resistant yellow reactive dye and preparation method thereof |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3598801A (en) * | 1967-01-09 | 1971-08-10 | Geigy Ag J R | Water-soluble azo-pyrimidine dyestuffs |
| JPS57195159A (en) * | 1981-05-15 | 1982-11-30 | Basf Ag | Reactive dye |
| JP2001164137A (en) * | 1999-12-13 | 2001-06-19 | Sumitomo Chem Co Ltd | Bisazo compound or its salt and their application to fiber material |
| CN1643078A (en) * | 2002-03-22 | 2005-07-20 | 德意志戴斯达纺织品及染料两合公司 | Water-soluble reactive mono- and di-azo dyes |
| WO2013008201A2 (en) * | 2011-07-12 | 2013-01-17 | Colourtex Industries Limited | Novel reactive dyes, there mixtures and processes thereof |
-
2016
- 2016-08-30 CN CN201610770892.2A patent/CN106398301A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3598801A (en) * | 1967-01-09 | 1971-08-10 | Geigy Ag J R | Water-soluble azo-pyrimidine dyestuffs |
| JPS57195159A (en) * | 1981-05-15 | 1982-11-30 | Basf Ag | Reactive dye |
| JP2001164137A (en) * | 1999-12-13 | 2001-06-19 | Sumitomo Chem Co Ltd | Bisazo compound or its salt and their application to fiber material |
| CN1643078A (en) * | 2002-03-22 | 2005-07-20 | 德意志戴斯达纺织品及染料两合公司 | Water-soluble reactive mono- and di-azo dyes |
| WO2013008201A2 (en) * | 2011-07-12 | 2013-01-17 | Colourtex Industries Limited | Novel reactive dyes, there mixtures and processes thereof |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116144195A (en) * | 2022-12-12 | 2023-05-23 | 江苏德美科化工有限公司 | High-performance alkali-resistant yellow reactive dye and preparation method thereof |
| CN116144195B (en) * | 2022-12-12 | 2024-04-02 | 江苏德美科化工有限公司 | High-performance alkali-resistant yellow reactive dye and preparation method thereof |
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| RJ01 | Rejection of invention patent application after publication | ||
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Application publication date: 20170215 |