CN104693141A - Disperse dye compound as well as preparation method and use of disperse dye compound - Google Patents
Disperse dye compound as well as preparation method and use of disperse dye compound Download PDFInfo
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- CN104693141A CN104693141A CN201510102466.7A CN201510102466A CN104693141A CN 104693141 A CN104693141 A CN 104693141A CN 201510102466 A CN201510102466 A CN 201510102466A CN 104693141 A CN104693141 A CN 104693141A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/58—Nitro radicals
-
- 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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/18—Preparation of azo dyes from other azo compounds by acylation of hydroxyl group or of mercapto group
- C09B43/26—Preparation of azo dyes from other azo compounds by acylation of hydroxyl group or of mercapto group with polyfunctional acylating agents
-
- 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
- D06P1/16—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 dispersed, e.g. acetate, dyestuffs
- D06P1/18—Azo 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
- 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
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/24—Polyamides; Polyurethanes
- D06P3/26—Polyamides; Polyurethanes using dispersed dyestuffs
-
- 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
- D06P3/34—Material containing ester groups
- D06P3/52—Polyesters
- D06P3/54—Polyesters using dispersed dyestuffs
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Dispersion Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
Abstract
The invention discloses a disperse dye compound as well as a preparation method and the use of the disperse dye compound. The structural formula of the disperse dye compound is as shown in a formula I which is as shown in the specification. The disperse dye compound is prepared by selecting the C.I. disperse blue 106 dye to be subjected to coupling reaction with a diformyl chlorine compound. When the disperse dye compound is applied to dyeing polyurethane or polylactic acid fibers, the washing fastness and the sublimation fastness can be obviously improved.
Description
Technical field:
The present invention relates to a kind of Novel disperse dyestuff, refer in particular to a kind of disperse dye compound and preparation method thereof and purposes.
Background technology:
Dispersed dye the earliest for cellulose acetate fibre, after develop rapidly along with the development of trevira (terylene).Present dispersed dye are various in style, chromatogram is complete, can be divided into azo-type, fear quinoid, methine type, ortho-nitrophenyl amine type etc. by structure.Wherein the most noticeable chemical structure is azo, fears quinoid dispersed dye.The dispersed dye of azo-type structure have than advantages such as more complete chromatogram, high Chromaticity intensity (i.e. high molar extinction coefficient), easy manufacture and good economy performance.Fear quinoid dispersed dye and have vividness and the feature such as high colour fastness to light and excellent dyeing behavior, but also there is obvious shortcoming, as lower in coloring intensity and price is more expensive.In recent years, due to heterocyclic dispersed dye bright in color light, coloring intensity is high, fastness ability good, has good hyperchromic effect and higher molar extinction coefficient, and has good dyeing behavior, becomes dyestuff circle and studies a more field.In addition, at exploitation, screening polyester superfine fibre with in dyestuff process, also find that heterocycle dispersed dye have better application performance than other type disperse dye, cause the extensive concern of investigator.The heterocyclic dye synthesized in recent years mainly through introducing the heteroatomss such as nitrogenous, sulphur, oxygen on the diazo component or coupling component of dyestuff, and they are mostly bright in colour, and applicability is strong, has vast potential for future development.
When dispersed dye are a class water-soluble very low, dyeing in water mainly with the non-ionic dye that subparticle be dispersion state existence.According to similar dissolve mutually theory, be mainly used in the dyeing of hydrophobic fibre as fibers such as polyester, polymeric amide and vinegar esters.But because fibrous texture is different, the dyeing behavior that same dyestuff shows on different fiber also has larger difference.At present, according to dyeing behavior and the processing requirement of different fiber, professional quarters screen dispersed dye, obtain the series special dispersed dye being applicable to a certain fiber or a certain technique, and titled with corresponding trade name, to meet the demand in market.
Along with tencel is as polyurethane fiber, acid fiber by polylactic with easily contaminate the appearance such as modified dacron (be called for short ECDP), existing dispersed dye are difficult to meet its dyeing behavior requirement, generally there is the phenomenons such as tinting strength is low, colour fastness is poor, only rely on screening and dyeing to improve and be difficult to tackle the problem at its root.Trace it to its cause, because the second-order transition temperature of these fibers is relatively low, the molecule segment space produced of moving in pars amorpha is more larger, the phenomenon that Yi Jinyi goes out is there is during disperse dyeing, illustrate that existing dispersed dye are large not to the avidity of this fibrid, when causing fiber to be heated, because thermophoresis from inside to outside occurs in dye molecule thermal motion aggravation.Therefore, the resistance to thermal mobility improving dispersed dye has become the study hotspot of current insider.
Summary of the invention:
A first aspect of the present invention object is to provide a kind of novel disperse dye compound, and these dispersed dye, to the dyeing of spandex, acid fiber by polylactic, have significant effect.
The technical scheme that the present invention takes is as follows:
A kind of disperse dye compound, its structural formula as shown in Equation 1:
Formula 1.
Above-mentioned disperse dye compound of the present invention, containing two azo dispersion dyes parents and two ester groups (-COO-), the feature of this structure is:
(1), molecular volume and the molecular weight of dyestuff is effectively increased, thus the contact surface added between dyestuff and fiber and Van der Waals force, improve dyestuff to the avidity of fiber.
The upper dye mechanism of dispersed dye shows, dispersed dye rely on Van der Waals force, between hydrogen bond and charge transfer molecular, the reactive force such as power combines with fiber.Van der Waals force size between dyestuff and fiber is decided by the Structure and form of molecule, and and contact area between them and intermolecular distance dependent.The relative molecular mass of general dyestuff is larger, and structure is more complicated, and conjugate system is longer, and line style, coplanarity are better, and is suitable for mutually with the molecular structure of fiber, then Van der Waals force is general larger.
(2), by introducing ester group (-COO-) this characteristic group, hydrogen bond can be formed with the hydrogen group that supplies in fiber, and being suitable for mutually with the structure of trevira.
(3) two independently color bases are contained, change that can not be too large to coloured light generation in, novel disperse dyes structure formula.
A second aspect of the present invention object is to provide a kind of preparation method of aforementioned disperse dye compound, it is characterized in that, comprises the following steps: select C.I. EX-SF DISPERSE BLUE EX-SF 300 106 dyestuff, carry out linked reaction, prepare described disperse dye compound with dimethyl chloride compound.
Further:
In the three-necked flask of 500ml, add 1.00g to have purified and through vacuum drying C.I. EX-SF DISPERSE BLUE EX-SF 300 106 dyestuff, add the appropriate 300ml methylene dichloride through processed and make solvent, stirring makes dispersed dye dissolve completely, add the triethylamine of 0.61g through processed, accurately take 0.40g dimethyl chloride compound, with appropriate reaction solvent dissolved dilution, in the reactor that slowly instillation is stirred in ice bath, under being warming up to room temperature, react 2-4h; Thin-layer sample application follows the tracks of reaction process, adds 100ml after completion of the reaction containing rare aqueous acid, extracting and separating, is revolved by dye liquor and steams removing dichloromethane solvent, then use appropriate sodium carbonate solution washing and filtering, and clear water washing obtains thick product 1.18g.
The thick product of disperse dye compound of preparation, then through dimethyl formamide recrystallization, obtain disperse dye compound sterling.
A third aspect of the present invention object is to provide the purposes of a kind of aforementioned disperse dye compound in spandex or polylactic acid fiber dyeing, confirm through experiment, adopt above-mentioned disperse dye compound, spandex, acid fiber by polylactic are dyeed, and colour fastness test is carried out to 1:1 standard dyeing sample, test result shows, the washing fastness of spandex and polylactic acid fiber dyeing sample is all comparatively significantly improved, and the fastness to dryheat of spandex tinctorial pattern also improves significantly.
Below in conjunction with the drawings and specific embodiments, the present invention is elaborated further:
Accompanying drawing illustrates:
Fig. 1 is the mass spectrum of disperse dye compound prepared by the embodiment of the present invention;
Fig. 2 is the nucleus magnetic resonance figure of disperse dye compound prepared by the embodiment of the present invention;
Fig. 3 is the Infrared spectroscopy comparison diagram of the disperse dye compound prepared of the embodiment of the present invention and C.I. EX-SF DISPERSE BLUE EX-SF 300 106;
Fig. 4 be the disperse dye compound prepared of the embodiment of the present invention and C.I. EX-SF DISPERSE BLUE EX-SF 300 106 absorption spectrum curve comparison diagram.
Embodiment:
Embodiment 1:
In the three-necked flask of 500ml, add 1.00g to have purified and through vacuum drying C.I. EX-SF DISPERSE BLUE EX-SF 300 106 dyestuff, add the appropriate 300ml methylene dichloride through processed and make solvent, stirring makes dispersed dye dissolve completely, add the triethylamine of 0.61g through processed, accurately take 0.40g dimethyl chloride compound, with appropriate reaction solvent dissolved dilution, in the reactor that slowly instillation is stirred in ice bath, under being warming up to room temperature, react 2-4h.Thin-layer sample application follows the tracks of reaction process, adds 100ml after completion of the reaction containing rare aqueous acid, extracting and separating, is revolved by dye liquor and steams removing dichloromethane solvent, then use appropriate sodium carbonate solution washing and filtering, and clear water washing obtains thick product 1.18g, and productive rate is 84.29%.
Thick product, again through dimethyl formamide recrystallization, obtains Novel disperse dyestuff pure compounds (hereinafter referred to as reactive monoazo dyestuffs).
Product confirms:
(1) molecular structural formula:
(3) molecular structure characterization:
Mass spectroscopy: MS (+ESI): m/z (%)=801 (100) [M+H]
+.
Nmr analysis: 1H NMR (400MHz, CDCl3) ppm 8.60 (s, 2H), 8.04 (s, 4H), 8.00 (d, J=9.2Hz, 2H), 6.72 (dd, J=9.2,2.8Hz, 2H), 6.69 (s, 2H), 4.59 (t, J=6.0Hz, 4H), 3.89 (t, J=6.0Hz, 4H), 3.65 (q, J=6.8Hz, 4H), 2.62 (s, 6H), 1.32 (t, J=6.8Hz, 6H).
Infrared spectroscopy: as shown in Figure 3.
From figure, carry out contrast find, 3200-3500cm in the infrared spectrogram of reactive monoazo dyestuffs
-1hydroxyl stretching vibration peak ν is there is not in scope
oH, increased newly and be positioned at 1718cm
-1the characteristic peak ν at place's ester group (-COO-)
c=O, and other peaks are substantially constant, illustrate that in C.I. EX-SF DISPERSE BLUE EX-SF 300 106, hydroxyl and p-phthaloyl chloride there occurs reaction, generate new coupling dispersed dye.
(4) spectral absorption performance:
Take 0.01 gram of reactive monoazo dyestuffs, dissolve constant volume at 100mlN, in dinethylformamide, diluting 10 times makes concentration be 0.01g/L, UV-2450 ultraviolet-visible pectrophotometer (Japanese Shimadzu Corporation) is adopted to measure absorption spectrum curve, and compared with same concentrations former dyestuff 0.01g/L C.I. EX-SF DISPERSE BLUE EX-SF 300 106 solution absorption spectra curve, see Fig. 4.
Can find from the absorption spectrum curve figure, compared with former dyestuff C.I. EX-SF DISPERSE BLUE EX-SF 300 106, the maximum absorption wavelength of reactive monoazo dyestuffs 3 offset by 14nm to shortwave direction, become 599nm, and molar extinction coefficient increases to some extent from original 613nm.After measured, specific performance index is as shown in table 1 below:
Table 1, dye absorber spectrum property parameter
| Dyestuff title | Maximum absorption wavelength/nm | Molar extinction coefficient ε |
| C.I. EX-SF DISPERSE BLUE EX-SF 300 106 | 613 | 3631 |
| Reactive monoazo dyestuffs 3 | 599 | 6856 |
(5) product fastness properties detects:
The reactive monoazo dyestuffs prepared by the present embodiment, with C.I. EX-SF DISPERSE BLUE EX-SF 300 106, is applied to the dyeing of spandex, acid fiber by polylactic respectively, and tests its dyeing behavior respectively as shown in table 2, table 3.
Testing method: accurately take 0.5000g reactive monoazo dyestuffs and 0.5000g dispersion agent NNO, put into mortar, add little water, grind, after 20min, transfer is settled to the volumetric flask of 500ml, be mixed with the mother liquor that dye content is 1g/L, draw the dye liquor that this mother liquor becomes different concns, dye 60min under 110 DEG C of conditions, obtain the dye sample of 1:1 standard color sample color depth value, C1S method in ISO 105-C06:2010 (E) standard is adopted to measure its Washing, ISO 105P01:1993 is adopted to measure color fastness to dry heat, adopt GB/T3920-2008, GB/T8427-2008 method measures friction and light fastness.
Table 2, dyestuff compare the fastness properties that spandex dyes
Table 3, the dyestuff fastness properties to polylactic acid fiber dyeing compares
From upper table experimental data: reactive monoazo dyestuffs has greatly improved than every fastness properties of former dyestuff C.I. EX-SF DISPERSE BLUE EX-SF 300 106, especially larger to the staining fastness increase rate of various fiber, reach the effect of expection imagination, illustrate that reactive monoazo dyestuffs has larger avidity to fiber really, dyestuff not easily from internal migration out.
Claims (5)
1. a disperse dye compound, its structural formula as shown in Equation 1:
formula 1.
2. a preparation method for disperse dye compound described in claim 1, is characterized in that, comprises the following steps: select C. I. EX-SF DISPERSE BLUE EX-SF 300 106 dyestuff, carry out linked reaction, prepare described disperse dye compound with dimethyl chloride compound.
3. the preparation method of a kind of disperse dye compound according to claim 2, it is characterized in that: in the three-necked flask of 500ml, add 1.00g to have purified and through vacuum drying C. I. EX-SF DISPERSE BLUE EX-SF 300 106 dyestuff, add the appropriate 300ml methylene dichloride through processed and make solvent, stirring makes dispersed dye dissolve completely, add the triethylamine of 0.61g through processed, accurately take 0.40g dimethyl chloride compound, with appropriate reaction solvent dissolved dilution, in the reactor that slowly instillation is stirred in ice bath, under being warming up to room temperature, react 2-4h; Thin-layer sample application follows the tracks of reaction process, adds 100ml after completion of the reaction containing rare aqueous acid, extracting and separating, is revolved by dye liquor and steams removing dichloromethane solvent, then use appropriate sodium carbonate solution washing and filtering, and clear water washing obtains thick product 1.18g.
4. the preparation method of a kind of disperse dye compound according to claim 3, is characterized in that: the thick product of disperse dye compound of preparation, then through dimethyl formamide recrystallization, obtains disperse dye compound sterling.
5. the purposes of disperse dye compound in spandex or polylactic acid fiber dyeing described in a claim 1.
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| CN201510102466.7A CN104693141A (en) | 2015-03-10 | 2015-03-10 | Disperse dye compound as well as preparation method and use of disperse dye compound |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104804464A (en) * | 2015-03-10 | 2015-07-29 | 绍兴文理学院 | Disperse dye compound as well as preparation method and application thereof |
| CN113152121A (en) * | 2021-02-09 | 2021-07-23 | 绍兴文理学院 | Orange coupled disperse dye compound and dyeing process thereof |
| CN113152122A (en) * | 2021-02-09 | 2021-07-23 | 绍兴文理学院 | Red coupled disperse dye compound and dyeing process thereof |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2060466A1 (en) * | 1991-02-20 | 1992-08-21 | Volker Bach | Bichromophoric methine dyes |
| US5214140A (en) * | 1990-02-15 | 1993-05-25 | Basf Aktiengesellschaft | Bichromophoric methine and azamethine dyes and process for transferring them |
| US5371266A (en) * | 1990-02-15 | 1994-12-06 | Basf Aktiengesellschaft | Bichromophoric cyano-containing methine dyes and transfer thereof |
| CN103952007A (en) * | 2014-04-28 | 2014-07-30 | 绍兴文理学院 | Crosslinking modification method of azo-disperse dye |
-
2015
- 2015-03-10 CN CN201510102466.7A patent/CN104693141A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5214140A (en) * | 1990-02-15 | 1993-05-25 | Basf Aktiengesellschaft | Bichromophoric methine and azamethine dyes and process for transferring them |
| US5371266A (en) * | 1990-02-15 | 1994-12-06 | Basf Aktiengesellschaft | Bichromophoric cyano-containing methine dyes and transfer thereof |
| CA2060466A1 (en) * | 1991-02-20 | 1992-08-21 | Volker Bach | Bichromophoric methine dyes |
| CN103952007A (en) * | 2014-04-28 | 2014-07-30 | 绍兴文理学院 | Crosslinking modification method of azo-disperse dye |
Non-Patent Citations (2)
| Title |
|---|
| JINGDONG LUO，等: "Synthesis and characterization of accordion main-chain azo-dye polymers for second-order optical non-linearity", 《POLYMER INTERNATIONAL》, vol. 49, no. 11, 31 December 2000 (2000-12-31), pages 1302 - 1307 * |
| 陈荣圻: "分散染料六十年发展概述（一）", 《染料与染色》, vol. 51, no. 6, 31 December 2014 (2014-12-31), pages 1 - 12 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104804464A (en) * | 2015-03-10 | 2015-07-29 | 绍兴文理学院 | Disperse dye compound as well as preparation method and application thereof |
| CN113152121A (en) * | 2021-02-09 | 2021-07-23 | 绍兴文理学院 | Orange coupled disperse dye compound and dyeing process thereof |
| CN113152122A (en) * | 2021-02-09 | 2021-07-23 | 绍兴文理学院 | Red coupled disperse dye compound and dyeing process thereof |
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Application publication date: 20150610 |