CN102618084A - Heterocyclic ring blue disperse dye and synthesizing method and application thereof - Google Patents
Heterocyclic ring blue disperse dye and synthesizing method and application thereof Download PDFInfo
- Publication number
- CN102618084A CN102618084A CN201210045264XA CN201210045264A CN102618084A CN 102618084 A CN102618084 A CN 102618084A CN 201210045264X A CN201210045264X A CN 201210045264XA CN 201210045264 A CN201210045264 A CN 201210045264A CN 102618084 A CN102618084 A CN 102618084A
- Authority
- CN
- China
- Prior art keywords
- dyeing
- dicyanoethyl
- blue
- dye
- modified wood
- 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.)
- Granted
Links
Images
Landscapes
- Coloring (AREA)
Abstract
The invention discloses a heterocyclic ring blue disperse dye and a synthesizing method and application thereof. A structural formula of the heterocyclic ring blue disperse dye is shown. In the formula, R=H, C1and CH3. The synthesizing method comprises the steps of dissolving 2-amino-3, 5-binitro thiophene in a sulfuric acid-phosphoric acid solution, diazotizing at the low temperature, respectively coupling the solution with N,N-dicyanoethylaniline, N,N-dicyanoethyl-m-chloroaniline and N,N-dicyanoethyl-m-methylaniline, performing cooling, crystallization and reduced-pressure filtration, and washing the solution to be neutral to obtain the blue disperse dye. The dye can be a single structure or can be prepared into a mixed structure, can be used for dyeing polyester fiber, cellulose acetate fiber and other synthetic fiber, also can be used for dyeing acetylated modified wood and cyanoethylated modified wood, have dark dyeing and good dyeing performance, embodies excellent color fastness, and dyeing color is bright-colored blue.
Description
Technical field
The present invention relates to the synthetic and Application Areas of fine chemical product.Be specifically related to the heterocycle blue disperse dye, relate to their compound method, also relate to their dyeing on the dyeing on the polyester piece good and acetylize, cyanoethylation modified wood.
Background technology
Single cyanoethylation product of aromatic amine is widely used in dispersed dye synthetic.For example, N-cyanoethyl aniline, N-ethyl-N-cyanoethyl aniline, N hydroxyethyl N cyanoethyl aniline, N-cyanoethyl Ortho-Chloro aniline, N-butyl-N-cyanoethyl aniline, N-second propyloic-N-cyanoethyl aniline etc. all have been used to the synthetic of azo dispersion dyes.But the double fluoride ethyl purification product of aromatic amine is few as the synthetic middle report that coupling component is applied to dispersed dye, and product the earliest mainly contains DISPERSE YELLOW 163, disperses tangerine 44 and disperses tangerine 45, but their diazo component is the aromatic amine with benzene ring structure.Over nearly 20 years; With heterocyclic aromatic amine; Like thiazole or benzothiazole aromatic amine derivant as diazo component, aromatic amine double fluoride ethyl purification product for the coupling component synthetic have heterocycle/two cyanoethyls be azo dispersion dyes in continuous appearance, but its coloured light is main with yellow, orange and orange basically; Its maximum absorption wavelength below 550nm, is seldom seen coloring intensity high, beautiful in colour and sticking colour fastness of washing and the high blue azo dispersion dyes of light fastness basically.
Dispersed dye are used widely to the dyeing on dacron fabric, cellulose acetate fabric and the mixed fiber fabric thereof; That timber also adopts basically is acid, alkalescence, directly, dyestuff such as activity dyes; Dispersed dye have than big-difference because of the polarity with timber, and dye uptake is low, and fastness is poor; Coloured light light is dark, so generally be not used in stained wood.
Summary of the invention
The present invention provides heterocycle blue disperse dye and its compound method; And with they dyeing to trevira, cellulose acetate and BLENDED FABRIC thereof; And, obtain having the blue fabric or the blue water-fast timber of outstanding each item colour fastness to the dyeing of acetylize modified wood, cyanoethylation modified wood.
Dyestuff of the present invention is one type of azo dispersion dyes with heterocycle/two cyanoethyl structures; Can in slightly acidic or weakly alkaline dye liquor, dye to trevira, cellulose acetate and BLENDED FABRIC thereof; Also can be used for dyeing to acetylize modified wood, cyanoethylation modified wood; The coloured light of coloring matter is blueness, has beautiful in colour, high Chromaticity intensity, the sticking colour fastness of high washing and high light fastness.
Technical scheme of the present invention is: amino-3 with 2-, the 5-dinitro thiophene is as diazo component, N, and N-dicyanoethyl aniline, N, N-dicyanoethyl meta-aminotoluene or N, N-dicyanoethyl m-chloro aniline obtains corresponding heterocycle azo compound for the coupling component; The chemical structure of general formula of said compound is:
General formula I, wherein R=H or R=Cl or R=CH
3
Contain in the compound of the structure shown in the general formula I one or more in the dyestuff of the present invention.
The preparation method of such blue heterocycle azo dispersed dye is: with 2-amino-3, the 5-dinitro thiophene is dissolved in H
3PO
4-H
2SO
4Mixing solutions in, under-5～20 ℃, carry out diazotization with Sodium Nitrite-sulfuric acid or nitrosyl sulfuric acid.Join N again, N-dicyanoethyl aniline, N, N-dicyanoethyl meta-aminotoluene or N, the H of N-dicyanoethyl m-chloro aniline
3PO
4-H
2SO
4Coupling solution in, ℃ carry out coupling at low temperatures-5～25, coupling is warmed up to 50～80 ℃ after accomplishing, insulation 2～12h changes brilliant, after filtration under diminished pressure, wash, drain, drying, solid dye.
Described H
3PO
4-H
2SO
4Mixing solutions in H
3PO
4Mass percent concentration 30～70%, H
2SO
4Mass percent concentration 20～40%.Described H
3PO
4-H
2SO
4Coupling solution in H
3PO
4Mass percentage concentration 20～40%, H
2SO
4Mass percent concentration 30～60%.
The structure of blue heterocycle azo dispersed dye of the present invention confirms that method is: synthetic drying solid dyestuff is carried out recrystallization, dry then with acetone; Analyze detection means through ultraviolet, infrared, nuclear-magnetism, mass spectrum and ultimate analysis etc., confirm its chemical structure and composition.Dyestuff maximum absorption wavelength of the present invention is one type of blue serial azo dispersion dyes that contains heterocycle and two cyanoethyl constitutional featuress at 575～599nm; Its molar extinction coefficient of such dyestuff is 4.2 * 10
4～4.6 * 10
4, embody the characteristic of high Chromaticity intensity.
Dyestuff of the present invention to the dyeing process of textile fibres is: synthetic drying solid dyestuff is carried out sand milling with certain amount of dispersant MF, water, granulated glass sphere, carry out spraying drying then, obtain corresponding commercial dye.Take by weighing given commodity dyestuff, synthetic fabrics and water; Add emulsifier op-10, PH regulator, under 60～140 ℃, polyester textile or cellulose acetate were dyeed after for some time with high temperature-pressure dyeing machine; Appearance is dyed in taking-up; After soaping, washing, painted fabric is blue, the be correlated with mensuration of fastness of the national standard of measuring according to relevant textiles fastness then.
Synthetic heterocyclic blue azo dispersion dyes expands to the dyeing to acetylize timber, cyanoethylation timber among the present invention, can open up the purposes of dispersed dye undoubtedly, increases the assortment of timber, improves the water resistance of coloured timber.
Dyestuff of the present invention to the dyeing process of chemical modification timber is: replace synthetic fabrics with acetylize modified wood, cyanoethylation modified wood, carry out according to the dyeing process of above-mentioned heterocycle azo dispersed dye to textile fibres.
The heterocycle azo dispersed dye of blueness of the present invention have lovely luster, high, outstanding, the dye uptake advantages of higher of each item colour fastness of coloring intensity.These heterocycle azo dispersed dye can be used for dyed polyester fiber, cellulose acetate and BLENDED FABRIC thereof in the scope of PH=3～9; The coloured light of DYED FABRICS is blue; Its washing (sticking look) fastness reaches 4～5 grades, and light fastness reaches 6～7 grades, and the dyeing dye uptake reaches 85～95%.These heterocycle azo dispersed dye also can be used for the dyeing of acetylize modified wood and cyanoethylation modified wood, and the coloured light of stained specimens is blue, and its washing (sticking look) fastness reaches 4～5 grades, and light fastness reaches 6～7 grades.Its result see attached list 1 with accompanying drawing 1.
Simultaneously; Also can be by above any two kinds; Or the compsn of three kinds of heterocyclic blue dispersion dyes formations is used for the dyeing of trevira, cellulose acetate and BLENDED FABRIC thereof; And be applicable to that the dyeing of acetylize modified wood and cyanoethylation modified wood, the coloured light of its product dyed thereby are similarly blue, and have beautiful in colour, high Chromaticity intensity, the sticking colour fastness of high washing and high light fastness.
Description of drawings
Accompanying drawing 1: heterocyclic blue dispersion dyes dyeing polyester piece good, acetylize China fir powder and cyanoethylation China fir powder figure.
Embodiment
Following examples are intended to explain the present invention rather than to further qualification of the present invention.
Embodiment 1
Title product (A
1) synthesis technique and tint applications
In having the 250mL there-necked flask of whisking appliance, add 28mL 85%H
3PO
4With 12mL 98%H
2SO
4, 10mL water stirs adding 4.73g 2-amino-3 down, and the 5-dinitro thiophene stirs down and slowly drips nitrosyl sulfuric acid, and is complete to diazotization reaction.Meanwhile, in having the 500mL beaker of whisking appliance, add 30mL water, 20mL 85%H
3PO
4, 32mL98%H
2SO
4, 4.98g N, N-dicyanoethyl aniline is cooled to 5 ℃.Slowly splash into diazonium salt under stirring, drip off, continue to react to the diazo component disappearance, suction filtration, washing is drained to neutral, and drying gets the brown solid dyestuff, λ
Max=575nm (acetone), ε=4.5 * 10
4C 48.05, and H 3.12, and N 24.64; IR (cm
-1, KBr), v:2925,2853,2248,1597,1547,1506,1455,841,756,685;
1H NMR (CDCl
3, 400MHz) δ: 2.71 (t, 4H, CH
2), 3.91 (t, 4H, CH
2), 6.77～7.53 (m, 4H, C
6H
3), 8.41 (s, 1H, C
4H); MS (m/z): 382,341,295,288,241,122.Institute's synthetic dyestuff is title product (A
1).
The above-mentioned dry product dyestuff that obtains is mixed with diffusant, and its ratio is dyestuff (dry product): dispersing agent MF: sodium lignosulfonate: water=1: 1: 1: 6.0, and sand milling to particle diameter is less than 1U, and spraying drying obtains commercial dye.In the dye vat that fills 200g water, add the above-mentioned dyestuff of 0.020g; Add emulsifier op-10,1mL HAc-NaAc (2.OM), 2.000 polyester piece goods, airtight dye vat is put into dyeing machinery; Slowly heat up; About 30min rises to 120 ℃ of insulation 40min, and the cooling back is taken out and dyed appearance, soaps, washes the back and be dark bright blue.According to textiles GB/T 3921-2008 standard testing its washing fastness of evaluation and its weathering color fastness of GB/T8427-1998 standard testing evaluation, the sticking colour fastness of its washing is 5 grades then, and light fastness is 7 grades.Using spectrophotometry to record the dyestuff dye uptake is 86.8%.
Replace polyester piece good to dye with acetylize China fir powder, dye appearance and be mazarine, the sticking colour fastness of washing is 5 grades, and the dyestuff dye uptake is 96.3%.Replace polyester piece good to dye with cyanoethylation China fir powder, dye appearance and be mazarine, the sticking colour fastness of washing is 4～5 grades, and dye uptake is 95.0%.
Embodiment 2
Title product (A
2) synthesis technique and tint applications
Press embodiment 1, use 5.43g N, N-dicyanoethyl meta-aminotoluene replaces N, and N-dicyanoethyl aniline gets the blue solid dyestuff, λ
Max=599nm (acetone), ε=4.6 * 10
4C 49.35, and H 3.79, and N 23.64; IR (cm
-1, KBr), v:2928,2854,2250,1602,1541,1496,1457,829,756,728,690;
1H NMR (CDCl
3, 400MHz) δ: 2.54 (t, 3H, CH
3), 2.73 (t, 4H, CH
2), 3.72 (t, 4H, CH
2), 6.60～7.53 (m, 3H, C
6H
3), 7.71 (s, 1H, C
4H); MS (m/z): 382,341,295,288,241,122.Institute's synthetic dyestuff is title product (A
2).
Press embodiment 1, adopt this dyestuff Dichlorodiphenyl Acetate fabric to dye, fabric is a bright blue, and the sticking colour fastness of washing is 5 grades, and light fastness is 7 grades, and dye uptake is 96.2%.
Replace the acetic acid fabric to dye with acetylize China fir powder, dye appearance and be bright blue, the sticking colour fastness of washing is 5 grades, and dye uptake is 99.2%.Replace polyester piece good to dye with cyanoethylation China fir powder, dye appearance and be bright blue, the sticking colour fastness of washing is 4～5 grades, and dye uptake is 98.1%.
Embodiment 3
Title product (A
3) synthesis technique and tint applications
Press embodiment 1, use 5.84g N, N-dicyanoethyl m-chloro aniline replaces N, and N-dicyanoethyl aniline gets the blue solid dyestuff, λ
Max=578nm (ethanol), ε=42 * 10
4C 44.21, and H 2.93, and N 22.47; IR (cm
-1, KBr), v:2924,2853,2252,1598,1543,1515,1498,1469,821,785,775,728;
1H NMR (CDCl
3, 400MHz) δ: 2.65 (t, 4H, CH
2), 3.79 (t, 4H, CH
2), 6.65～7.21 (m, 3H, C
6H
3), 7.52 (s, 1H, C
4H); MS (m/z): 382,341,295,288,241,122.Institute's synthetic dyestuff is title product (A
3).
Press embodiment 1, with the dyestuff of this dyestuff replacement of 0.010g embodiment 1, to polyester piece good dyeing, fabric is light blue, and the sticking colour fastness of washing is 4～5 grades, and light fastness is 7 grades, and dye uptake is 86.9%.
Subordinate list 1, the result of heterocyclic blue dispersion dyes dyeing synthetic fabrics of the present invention and chemical modification timber
Claims (7)
1. the heterocycle blue disperse dye is characterized in that, contains in the compound of structure shown in the general formula I one or more in the described dyestuff, and this compound is made up of diazo component and coupling component; Its diazo component is a 2-amino-3, the 5-dinitro thiophene; Coupling component is N, N-dicyanoethyl aniline, or N, N-dicyanoethyl m-chloro aniline or N, monomethylaniline between the N-dicyanoethyl;
General formula I, wherein: R=H, Cl or CH
3
2. the preparation method of the said dyestuff of claim 1 is characterized in that, with 2-amino-3, the 5-dinitro thiophene is dissolved in H
3PO
4-H
2SO
4Mixing solutions in, under-5～20 ℃, carry out diazotization with Sodium Nitrite-sulfuric acid or nitrosyl sulfuric acid; Join again and contain N, N-dicyanoethyl aniline, N, N-dicyanoethyl meta-aminotoluene or N, the H of N-dicyanoethyl m-chloro aniline
3PO
4-H
2SO
4Coupling solution in, ℃ carry out coupling at low temperatures-5～25, coupling is warmed up to 50～80 ℃ after accomplishing, insulation 2～12h changes brilliant, after filtration under diminished pressure, wash, drain, drying, solid dye.
3. method according to claim 2 is characterized in that, described H
3PO
4-H
2SO
4Mixing solutions in H
3PO
4Mass percent concentration 30～70%, H
2SO
4Mass percent concentration 20～40%; Described H
3PO
4-H
2SO
4H in the coupling solution
3PO
4Mass percentage concentration 20～40%, H
2SO
4Mass percent concentration 30～60%.
4. the application of the described heterocyclic blue dispersion dyes of claim 1 is applicable to the dyeing of trevira, cellulose acetate or their BLENDED FABRIC, and the coloured light of its DYED FABRICS is blue.
5. the application of the described heterocyclic blue dispersion dyes of claim 1 is applicable to the dyeing of acetylize modified wood or cyanoethylation modified wood, and the coloured light that obtains stained wood is blue.
6. according to the described application of claim 5, the dyeing of acetylize modified wood or cyanoethylation modified wood, its timber can be wood powder, wood chip, sheet material or round log.
7. according to claim 4,5 or 6 described application, in the dyeing course, dyeing temperature carries out under 60～140 ℃, and dyeing time is 0.5～10h.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210045264XA CN102618084B (en) | 2012-02-27 | 2012-02-27 | Heterocyclic ring blue disperse dye and synthesizing method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210045264XA CN102618084B (en) | 2012-02-27 | 2012-02-27 | Heterocyclic ring blue disperse dye and synthesizing method and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN102618084A true CN102618084A (en) | 2012-08-01 |
| CN102618084B CN102618084B (en) | 2013-11-27 |
Family
ID=46558309
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201210045264XA Active CN102618084B (en) | 2012-02-27 | 2012-02-27 | Heterocyclic ring blue disperse dye and synthesizing method and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN102618084B (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103602095A (en) * | 2013-09-10 | 2014-02-26 | 江苏亚邦染料股份有限公司 | Monoazo-type disperse dyes, preparation method thereof and applications thereof |
| WO2018106925A1 (en) * | 2016-12-08 | 2018-06-14 | Electronics For Imaging, Inc. | Coloration of acetylated wood |
| US10293515B2 (en) | 2016-12-08 | 2019-05-21 | Electronic For Imaging, Inc. | Coloration of acetylated wood |
| CN115521636A (en) * | 2022-10-24 | 2022-12-27 | 浙江博澳新材料股份有限公司 | Dicyan-containing sun-proof anthraquinone disperse dye and preparation method thereof |
Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2612792A1 (en) * | 1975-03-25 | 1976-10-07 | Ici Ltd | DISPERSE MONOAZO DYES |
| EP0109857A1 (en) * | 1982-11-22 | 1984-05-30 | Research Association Of Synthetic Dyestuffs | Monoazo dye for synthetic fibers |
| GB2163768A (en) * | 1984-08-30 | 1986-03-05 | Sandoz Ltd | Thienyl-azo disperse dyes and intermediate thiophens |
| CN1099776A (en) * | 1993-05-06 | 1995-03-08 | 希巴-盖吉股份公司 | Azo dyes |
| CN1131689A (en) * | 1994-12-23 | 1996-09-25 | Basf公司 | Preparation of benzothiazolylazoanilines |
| JPH1077424A (en) * | 1996-07-08 | 1998-03-24 | Sumitomo Chem Co Ltd | Monoazo compound and method for dyeing or printing hydrophobic fiber therewith |
| JPH10306222A (en) * | 1997-05-08 | 1998-11-17 | Sumitomo Chem Co Ltd | Disperse dye for new synthetic fiber |
| JPH1129716A (en) * | 1997-05-14 | 1999-02-02 | Sumitomo Chem Co Ltd | Disperse dye composition |
| CA2700929A1 (en) * | 2007-09-28 | 2009-04-02 | Dystar Colours Deutschland Gmbh | Preparations comprising disperse dye and/or uv absorber |
-
2012
- 2012-02-27 CN CN201210045264XA patent/CN102618084B/en active Active
Patent Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2612792A1 (en) * | 1975-03-25 | 1976-10-07 | Ici Ltd | DISPERSE MONOAZO DYES |
| EP0109857A1 (en) * | 1982-11-22 | 1984-05-30 | Research Association Of Synthetic Dyestuffs | Monoazo dye for synthetic fibers |
| GB2163768A (en) * | 1984-08-30 | 1986-03-05 | Sandoz Ltd | Thienyl-azo disperse dyes and intermediate thiophens |
| CN1099776A (en) * | 1993-05-06 | 1995-03-08 | 希巴-盖吉股份公司 | Azo dyes |
| CN1131689A (en) * | 1994-12-23 | 1996-09-25 | Basf公司 | Preparation of benzothiazolylazoanilines |
| JPH1077424A (en) * | 1996-07-08 | 1998-03-24 | Sumitomo Chem Co Ltd | Monoazo compound and method for dyeing or printing hydrophobic fiber therewith |
| JPH10306222A (en) * | 1997-05-08 | 1998-11-17 | Sumitomo Chem Co Ltd | Disperse dye for new synthetic fiber |
| JPH1129716A (en) * | 1997-05-14 | 1999-02-02 | Sumitomo Chem Co Ltd | Disperse dye composition |
| CA2700929A1 (en) * | 2007-09-28 | 2009-04-02 | Dystar Colours Deutschland Gmbh | Preparations comprising disperse dye and/or uv absorber |
Non-Patent Citations (2)
| Title |
|---|
| 刘广文: "《染料加工技术》", 30 April 1999, article "《染料加工技术》", pages: 168 - 2 * |
| 赵莹等: "偶氮分散染料对氰乙基化杉木粉染色的研究", 《第四届全国生物质材料科学与技术学术研讨会》, 21 October 2011 (2011-10-21), pages 262 - 1 * |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103602095A (en) * | 2013-09-10 | 2014-02-26 | 江苏亚邦染料股份有限公司 | Monoazo-type disperse dyes, preparation method thereof and applications thereof |
| CN103602095B (en) * | 2013-09-10 | 2016-04-20 | 江苏亚邦染料股份有限公司 | One class Monoazo type dispersed dye, preparation method and application |
| WO2018106925A1 (en) * | 2016-12-08 | 2018-06-14 | Electronics For Imaging, Inc. | Coloration of acetylated wood |
| US10293515B2 (en) | 2016-12-08 | 2019-05-21 | Electronic For Imaging, Inc. | Coloration of acetylated wood |
| US10315332B2 (en) | 2016-12-08 | 2019-06-11 | Electronics For Imaging, Inc. | Coloration of acetylated wood |
| CN110267783A (en) * | 2016-12-08 | 2019-09-20 | 图像电子公司 | The coloring of acetylate wood |
| CN115521636A (en) * | 2022-10-24 | 2022-12-27 | 浙江博澳新材料股份有限公司 | Dicyan-containing sun-proof anthraquinone disperse dye and preparation method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN102618084B (en) | 2013-11-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN102031017B (en) | Disperse dye composition and application thereof | |
| CN102782210B (en) | Disperse azo dyes | |
| KR101984771B1 (en) | Black disperse dye composition for textile printing | |
| CN102746713A (en) | Blue-to-black disperse dye composition | |
| CN102618084B (en) | Heterocyclic ring blue disperse dye and synthesizing method and application thereof | |
| CN101067050B (en) | Disperse black dye composition | |
| CN104194381A (en) | Crosslinkable active disperse dye compound as well as preparation method and application thereof | |
| CN102796400A (en) | Yellow azo metallized dye composition, method and application thereof | |
| KR101387104B1 (en) | Disperse dye for polylactic acid fibers and black dye composition comprising thereof | |
| CN104087008B (en) | A kind of disperse dye compound, preparation method and application thereof | |
| CN103525121B (en) | One class azoic diphenylamine type dispersed dye and application thereof | |
| KR100581542B1 (en) | Black and navy blue disperse dye composition having excellent moisture resistance | |
| CN102086307A (en) | N,N-diacetoxyethyl-m-chloroaniline series azo dyes | |
| CN112574594B (en) | Disperse yellow-orange dye composition and product thereof | |
| CN104592782A (en) | Azoic disperse dye suitable for dyeing in acidic-alkaline bath as well preparation method and application thereof | |
| KR102137478B1 (en) | Brilliant blue azo dye and method of preparation thereof, and its use | |
| CN105111104B (en) | Disperse dye monomer compound, disperse dye preparation and applications of disperse dye preparation | |
| CN105238094B (en) | A kind of feux rouges blueness azo dispersion dyes with intensity of colour occurred frequently and preparation method thereof | |
| CN105542508B (en) | A kind of dispersion dyes monomer compound and its preparation method and application | |
| CN103881412A (en) | Mono-azo disperse dye compound and preparation method thereof | |
| CN103602095B (en) | One class Monoazo type dispersed dye, preparation method and application | |
| CN111423741A (en) | Disperse yellow dye and synthetic method thereof | |
| KR100256321B1 (en) | New blue azo dyes of high fastness | |
| CN105733291B (en) | A kind of high shifting red colouration dispersion dyes monomer compound and its preparation method and application | |
| CN104744964B (en) | A kind of dispersed blue dye monomeric compound and disperse dyes |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| C41 | Transfer of patent application or patent right or utility model | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20160728 Address after: 312369 Shangyu, Shaoxing, Hangzhou Bay Industrial Park, No. East Road, No. seven, No. 1 Patentee after: Zhejiang Dibang Chemical Co., Ltd. Address before: 410004 Shaoshan South Road, Hunan, No. 498, No. Patentee before: Central South University of Forestry and Technology |