CN105623298A - Orange disperse dye compound and application thereof - Google Patents
Orange disperse dye compound and application thereof Download PDFInfo
- Publication number
- CN105623298A CN105623298A CN201610104848.8A CN201610104848A CN105623298A CN 105623298 A CN105623298 A CN 105623298A CN 201610104848 A CN201610104848 A CN 201610104848A CN 105623298 A CN105623298 A CN 105623298A
- Authority
- CN
- China
- Prior art keywords
- disperse dye
- orange disperse
- dye compound
- orange
- 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.)
- Granted
Links
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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
-
- 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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/0041—Blends of pigments; Mixtured crystals; Solid solutions mixtures containing one azo dye
-
- 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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/0046—Mixtures of two or more azo dyes
- C09B67/0051—Mixtures of two or more azo dyes mixture of two or more monoazo 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
- D06P1/16—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
- D06P3/34—Material containing ester groups
- D06P3/52—Polyesters
- D06P3/54—Polyesters 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
- D06P3/82—Textiles which contain different kinds of fibres
- D06P3/8204—Textiles which contain different kinds of fibres fibres of different chemical nature
- D06P3/8214—Textiles which contain different kinds of fibres fibres of different chemical nature mixtures of fibres containing ester and amide groups
Abstract
The invention discloses an orange disperse dye compound and the application thereof.The structural formula of the orange disperse dye compound is shown in the formula (I), wherein X1 and X2 are hydrogen, chlorine or bromine, and R is methyl, ethyl, methoxyl, chlorine or bromine.The application of the orange disperse dye compound in hydrophobic fiber material dyeing is provided.When the dye is applied to hydrophobic fiber material dyeing, color is bright, elevating power is high, color fastness is high, and sublimation fastness and washing fastness are remarkable.
Description
(1) technical field
The present invention relates to a kind of orange disperse dye compound and application thereof, especially a kind of azo-type orange disperse dye compound and the application in hydrophobic fiber material is printed and dyed thereof.
(2) technical background
Development along with super fine denier polyester fiber, and wash/the development of the high-grade blend fabric such as ammonia, polyester cotton, existing disperse dyes can not meet its dyeing demand when printing and dyeing, as not good in dyeing color fastness, particularly washing fastness shortcoming, dyeing time loose colour more etc. In orange disperse dye, C.I. disperse orange 288 makes large usage quantity, is widely used because of advantages such as its production technology are simple, cost is low, bright in colour, but it is still to be improved in fastness to sublimation and washing fastness.
(3) summary of the invention
Present invention aim at: provide a kind of orange disperse dye compound, this application is bright in colour when hydrophobic fiber material is printed and dyed, lifting force color fastness good, every is excellent, and special fastness to sublimation and washing fastness highlight.
The technical solution used in the present invention is:
A kind of orange disperse dye compound, its structure is such as shown in formula I:
In formula I, X1��X2Each standing alone as hydrogen, chlorine or bromine, R is methyl, ethyl, methoxyl group, chlorine or bromine.
Further, R is ortho position or para-orientating group.
Further, described orange disperse dye compound is one of following formula:
Again further, described orange disperse dye compound is formula (I-1).
Orange disperse dye compound of the present invention can be prepared by diazotising well known in the art, coupling reaction mode, specifically include following steps: formula II compound is carried out diazotising by (1) in acid medium with nitrosyl sulfuric acid, control temperature between 0��20 DEG C; (2) by formula III compound stirring to pulp in acid medium, add the diazol that step (1) obtains, control temperature between 0��10 DEG C, carry out coupling reaction; (3) material is warming up to 70��80 DEG C after terminating and is incubated 2��4 hours by reaction, then sucking filtration, washing are to neutral, prepare described orange disperse dye compound;
In formula II and formula III, X1��X2, R the same formula I of definition.
In the present invention, formula II and formula III compound can be prepared by method well known in the art, it is possible to adopt commercial goods.
The invention provides the application in hydrophobic fiber material is printed and dyed of the described orange disperse dye compound.
Described orange disperse dye compound be applied to dyeing, stamp time need to carry out commercial treatment, generally needed to be added auxiliary agent and disperse, for instance auxiliary agent, water existence under carry out corpusculed with the pulverizer such as sand mill or grinder. Therefore the invention provides a kind of orange disperse dye, including described orange disperse dye compound and auxiliary agent. Dispersant conventional when described auxiliary agent is disperse dyes commercialization, diffusant, wetting agent and surfactant etc., it is preferable that one of following or wherein arbitrarily several mixture: the anionic dispersing agents such as naphthalene sulfonic acid-formaldehyde condensation product, alkyl naphthalene sulfonic acid formaldehyde condensation products, benzyl naphthalene sulfonic formaldehyde condensation compound, lignosulfonates. Specifically, naphthalene sulfonic acid-formaldehyde condensation product is dispersing agent NNO such as, alkyl naphthalene sulfonic acid formaldehyde condensation products such as Dispersant MF (condensation compound of methyl naphthalene sulfonic acid and formaldehyde), benzyl naphthalene sulfonic formaldehyde condensation compound such as dispersing agent CNF etc., lignosulfonates such as sodium lignin sulfonate (such as commercial dispersants Reax83A, Reax85A) etc. Described orange disperse dye compound and auxiliary agent mass ratio are 1:0.2��5. The orange disperse dye of the present invention can liquid after corpusculed, emulsifiable paste state or the powdery after being dried with spray drying method etc., graininess supply printing and dyeing.
Orange disperse dye manufactured according to the present invention, can adopt common dip method, pad-dyeing method to dye, it is also possible in direct printing. Wherein, common dip method, as polyester textile is carried out pretreatment, is put in dye vat and is contaminated, and dye finishes, and cold water wash is to neutral, and strand is dry, then carries out reduction cleaning, dries; Direct printing, as fabric carries out dye pre-treatment, is dried, setting, prints disperse dyes mill base, then evaporates, utilize decatize mode to make the dye fixing on fabric, finally wash, stentering forming on printing machine.
The orange disperse dye that the present invention prepares is utilized to be particularly well-suited to the printing and dyeing of hydrophobic fiber material, printing and dyeing including hydrophobic fibre blending that is semi-synthetic or that synthesize, it is particularly suited for the printing and dyeing of polyester fiber, uniform hue, every color fastness excellence can be obtained, particularly there is the washability of excellence and splendid resistance to sublimability, be also applied for medium-to-high grade fabric such as super fine denier fabric, polyester cotton, wash/printing and dyeing of the blend fabric such as ammonia.
In addition, orange disperse dye compound of the present invention can also with the composite dye species obtaining various tone of other disperse dye compound, as can with the disperse blue of the dyestuff composite acquisition excellent performances such as C.I. disperse violet 93, C.I. disperse blue 291, C.I. disperse blue 291:1, C.I. Disperse Blue-79, the dye species such as black.
Compared with prior art, the beneficial effects of the present invention is: when orange disperse dye compound provided by the invention is applied to hydrophobic fiber material printing and dyeing, bright in colour, lifting force color fastness excellence good, every, special fastness to sublimation and washing fastness highlight.
(4) detailed description of the invention
Below in conjunction with embodiment, the invention will be further described, but protection scope of the present invention is not limited to that.
Embodiment 1:
The preparation of coupling component: put into the aniline of 0.1mol in 250ml container, the propylene cyanogen of 0.12mol, the water of 50mol, is warmed up to 90 DEG C, is incubated 10h, cooling is simultaneously introduced the methanol of 30mol, at 0��5 DEG C of insulated and stirred 12h, crystallization is filtered, and washs with the methanol of 20mol, washed post-drying, obtains single cyanogen compound standby; The diethylaminoethanol of 0.1mol is put in 250ml container, the soda of 0.2mol, 0.05mol single cyanogen compound obtained above, it is warmed up to 80 DEG C, puts into the KI of 0.1mol, be incubated 12h, cool to 40 DEG C, adding the water of 50mol, crystallization is filtered, and obtains the coupling component shown in formula (III-1).
Diazotising: in the container of 250ml, puts into the water of 1.38mol, and cooling adds 98% concentrated sulphuric acid of 0.88mol, continues to be cooled to 10 DEG C, adds the paranitroanilinum of 0.1mol, and temperature controls to stir 4h at 20��30 DEG C; Slowly drip the nitrosyl sulfuric acid of 0.105mol at 10��15 DEG C, control time for adding in 6��7h, continue stirring 4h after dripping, obtain diazo liquid (standby).
Coupling reaction: put into the water of 55.5mol in 2L container, 98% concentrated sulphuric acid of 0.5mol, formula (III-1) coupling component of 0.1mol, pull an oar half an hour; The diazo liquid of above-mentioned preparation is dripped in 20min, control 0��5 DEG C of coupling reaction 5��6h of temperature, (with oozing circle experiment detection reaction end) after reacting completely, material is warmed up to 75 DEG C, being incubated 3h, sucking filtration again, washing is to neutral, obtaining the dye composition shown in formula (I-1), in DMF solution, �� max is 465nm. Be subsequently adding auxiliary agent MF, water grinds uniformly, and namely drying and dehydrating obtains disperse dyes, and wherein, the weight ratio of MF and dye composition is 1.6:1, and the water yield is 2 times of auxiliary agent MF and dye composition weight sum.
Embodiment 2��15:
The preparation of coupling component: the preparation method of coupling component described in embodiment 1, intermediate feed diethylaminoethanol is replaced with respectively 4-methoxybenzyl chloride, 4-bromine benzyl chloride, 4-chlorine benzyl chloride, 2-ethylmercury chloride benzyl, the intermediate shown in formula III structure in embodiment 2,3,4 and 13 can be prepared in table 1 below respectively.
The preparation of dyestuff: the diazo coupling method described in embodiment 1, the difference is that the compound that raw material diazo component, coupling component are replaced to the formula II in table 1 below, formula III, obtain the dye composition shown in table and the �� max in DMF solution thereof, be subsequently adding auxiliary agent MF, water grinds uniformly, namely drying and dehydrating obtains disperse dyes, wherein, the weight ratio of MF and dye composition is 1.6:1, the water yield is 2 times of auxiliary agent MF and dye composition weight sum, can be dyed by fabric orange when being applied to dyeing:
Table 1 raw material and dye composition
Embodiment 16:
The preparation of coupling component: prepare the coupling component shown in formula (III-1) by the method described in embodiment 1.
Diazotising: add 98% concentrated sulphuric acid of 0.88mol, the nitrosyl sulfuric acid of 0.105mol in 250ml container, cool to 0��5 DEG C, control to add the 2 of 0.1mol in 3��4h, 6-dichloro paranitroanilinum, is incubated 3h, obtains diazo liquid (standby) after adding.
Coupling reaction: put into the water of 55mol in 2L container, 98% concentrated sulphuric acid of 0.2mol, formula (III-1) coupling component of 0.1mol, pull an oar half an hour, control to drip in 1��2h the diazo liquid of above-mentioned preparation, control 0��5 DEG C of coupling reaction 5��6h of temperature, (with oozing circle experiment detection reaction end) after reacting completely, material is warmed up to 75 DEG C, being incubated 3h, sucking filtration again, washing is to neutral, obtaining the dye composition shown in formula (I-16), in DMF solution, �� max is 420nm. Be subsequently adding auxiliary agent MF, water grinds uniformly, and namely drying and dehydrating obtains disperse dyes, and wherein, the weight ratio of MF and dye composition is 1.6:1, and the water yield is 2 times of auxiliary agent MF and dye composition weight sum.
Embodiment 17��25:
According to the preparation method described in embodiment 16, the difference is that the compound that raw material diazo component, coupling component are replaced to the formula II in table 2 below, formula III, obtain the dye composition shown in table and the �� max in DMF solution thereof, be subsequently adding auxiliary agent MF, water grinds uniformly, namely drying and dehydrating obtains disperse dyes, wherein, the weight ratio of MF and dye composition is 1.6:1, the water yield is 2 times of auxiliary agent MF and dye composition weight sum, can be dyed by fabric orange when being applied to dyeing:
Table 2 raw material and dye composition
Comparative example 1:
By C.I. disperse orange 288 conventional on the market as a comparison case, its structure is as follows:
Disperse dyes are prepared according to the method for embodiment 1.
Tint applications example 26:
Weigh disperse dyes, the disperse dyes shown in comparative example 1 that 3 grams of embodiment 1-25 prepare respectively, it is dispersed in 500 milliliters of water, after drawing 20 milliliters, the water with 80 milliliters mixes, pH to 4.5 is adjusted with acetic acid, put into 4 grams of polyester textiles, it is warming up to 60 DEG C, continues with about 1 DEG C/min gradient increased temperature to 130 DEG C, insulation dyeing 45 minutes. Then being cooled to about 80 DEG C and use hot water wash 10min, dry, the method described in GB/T5718-1997, GB/T3921-2008 that is respectively adopted measures its resistance to distillation and water-fastness color fastness, and measurement result is shown in table 1 below:
Table 1
Tint applications example 27:
Weigh disperse dyes, the disperse dyes shown in comparative example 1 that 4 grams of embodiment 1-25 prepare respectively, it is dispersed in 500 milliliters of water, after drawing 20 milliliters, the water with 80 milliliters mixes, pH to 4.5 is adjusted with acetic acid, put into 4 grams of super fine polyester cloth, it is warming up to 60 DEG C, continues with about 1 DEG C/min gradient increased temperature to 130 DEG C, insulation dyeing 45 minutes. Then being cooled to about 80 DEG C and use hot water wash 10min, dry, the method described in ISO105-P01, GB/T3921-2008 that is respectively adopted measures its resistance to distillation and water-fastness color fastness, and measurement result is shown in table 2 below:
Table 2
From above-mentioned table 1, table 2, orange disperse dye provided by the invention, when application polyester textile or the dyeing of ultra-fine polyester textile, fastness to sublimation terylene staining fastness, water-fastness vinegar fibre staining fastness, nylon staining fastness and Pilus Caprae seu Ovis staining fastness are significantly better than that C.I. disperse orange 288.
Claims (8)
1. an orange disperse dye compound, its structure is such as shown in formula I:
In formula I, X1��X2Each standing alone as hydrogen, chlorine or bromine, R is methyl, ethyl, methoxyl group, chlorine or bromine.
2. orange disperse dye compound as claimed in claim 1, it is characterised in that: R is ortho position or para-orientating group.
3. orange disperse dye compound as claimed in claim 1, it is characterised in that: described orange disperse dye compound is one of following formula:
4. orange disperse dye compound as claimed in claim 1, it is characterised in that: described orange disperse dye compound is:
5. the orange disperse dye compound as claimed in claim 1 application in hydrophobic fiber material is printed and dyed.
6. an orange disperse dye, including orange disperse dye compound as claimed in claim 1 and auxiliary agent.
7. orange disperse dye as claimed in claim 6, it is characterised in that: described auxiliary agent is one of following or wherein arbitrarily several mixture: the anionic dispersing agents such as naphthalene sulfonic acid-formaldehyde condensation product, alkyl naphthalene sulfonic acid formaldehyde condensation products, benzyl naphthalene sulfonic formaldehyde condensation compound, lignosulfonates.
8. orange disperse dye as claimed in claims 6 or 7, it is characterised in that: described orange disperse dye compound and auxiliary agent mass ratio are 1:0.2��5.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610104848.8A CN105623298B (en) | 2016-02-25 | 2016-02-25 | A kind of orange disperse dye compound and its application |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610104848.8A CN105623298B (en) | 2016-02-25 | 2016-02-25 | A kind of orange disperse dye compound and its application |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN105623298A true CN105623298A (en) | 2016-06-01 |
| CN105623298B CN105623298B (en) | 2018-08-10 |
Family
ID=56038668
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610104848.8A Active CN105623298B (en) | 2016-02-25 | 2016-02-25 | A kind of orange disperse dye compound and its application |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN105623298B (en) |
Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2105361A (en) * | 1981-08-05 | 1983-03-23 | Yorkshire Chemicals Ltd | Azo disperse dyes and processes for their preparation |
| CN1230575A (en) * | 1998-03-23 | 1999-10-06 | 戴斯塔纺织纤维股份有限公司德国两和公司 | Disperse azo dye mixtures |
| CN101007908A (en) * | 1998-03-23 | 2007-08-01 | 戴斯塔纺织纤维股份有限公司德国两和公司 | Disperse azo dye mixtures |
| CN101265369A (en) * | 2008-05-14 | 2008-09-17 | 蓬莱华茂精细化工有限公司 | Azo dye composition and application thereof |
| CN102660145A (en) * | 2012-04-28 | 2012-09-12 | 浙江万丰化工有限公司 | Disperse dye composition for disperse/reactive dye combination printing, and preparation and application thereof |
| CN102660146A (en) * | 2012-04-28 | 2012-09-12 | 浙江万丰化工有限公司 | Oxidation-resistant disperse dye composition and preparation and application thereof |
| CN103450706A (en) * | 2013-09-07 | 2013-12-18 | 张家港市杨舍丝印工艺厂 | Dye composition (red brown) and preparation method thereof |
| KR20130137760A (en) * | 2012-06-08 | 2013-12-18 | 공명도 | Orange disperse dye composition having excellent moisture resistance |
| CN104151866A (en) * | 2014-07-22 | 2014-11-19 | 俞杏英 | Alkali-resistant disperse dye composition based on thiazole heterocycle red dye containing benzoyloxy group and application of alkali-resistant disperse dye composition |
-
2016
- 2016-02-25 CN CN201610104848.8A patent/CN105623298B/en active Active
Patent Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2105361A (en) * | 1981-08-05 | 1983-03-23 | Yorkshire Chemicals Ltd | Azo disperse dyes and processes for their preparation |
| CN1230575A (en) * | 1998-03-23 | 1999-10-06 | 戴斯塔纺织纤维股份有限公司德国两和公司 | Disperse azo dye mixtures |
| CN101007908A (en) * | 1998-03-23 | 2007-08-01 | 戴斯塔纺织纤维股份有限公司德国两和公司 | Disperse azo dye mixtures |
| CN101265369A (en) * | 2008-05-14 | 2008-09-17 | 蓬莱华茂精细化工有限公司 | Azo dye composition and application thereof |
| CN102660145A (en) * | 2012-04-28 | 2012-09-12 | 浙江万丰化工有限公司 | Disperse dye composition for disperse/reactive dye combination printing, and preparation and application thereof |
| CN102660146A (en) * | 2012-04-28 | 2012-09-12 | 浙江万丰化工有限公司 | Oxidation-resistant disperse dye composition and preparation and application thereof |
| KR20130137760A (en) * | 2012-06-08 | 2013-12-18 | 공명도 | Orange disperse dye composition having excellent moisture resistance |
| CN103450706A (en) * | 2013-09-07 | 2013-12-18 | 张家港市杨舍丝印工艺厂 | Dye composition (red brown) and preparation method thereof |
| CN104151866A (en) * | 2014-07-22 | 2014-11-19 | 俞杏英 | Alkali-resistant disperse dye composition based on thiazole heterocycle red dye containing benzoyloxy group and application of alkali-resistant disperse dye composition |
Non-Patent Citations (1)
| Title |
|---|
| 杨新玮: "《化工产品手册 染料》", 31 January 2005, 化学工业出版社 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN105623298B (en) | 2018-08-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN100503740C (en) | Dispersed black dye composition | |
| CN101323712B (en) | Dispersed black dye composition | |
| CN101768375B (en) | Black disperse dye composition | |
| CN103194093B (en) | Composition of blue to black disperse dyes | |
| CN102603572B (en) | Monoazo compound as well as preparation method and application thereof | |
| CN101935465B (en) | Disperse yellow brown dye composition | |
| CN102516811B (en) | Disperse black dye composition | |
| CN101735664B (en) | Disperse scarlet dye composition | |
| CN100422270C (en) | Composite disperse red dye composition | |
| CN102746712A (en) | Disperse dye composition, dye product and application | |
| CN107418249B (en) | A kind of bright blue dyestuff of economy composite type dispersion | |
| CN103113759A (en) | Red disperse dye composition, and preparation method and application thereof | |
| CN102816453B (en) | Disperse dye monomeric compound and disperse dye | |
| CN101275039B (en) | Disperse orange dye composition | |
| CN103194095B (en) | Dispersed blue-to-black dye composition | |
| CN104945954B (en) | A kind of dispersion red dye composition and dye preparations | |
| CN101760046A (en) | Dispersive black dye composition | |
| CN102443280B (en) | Dispersed blue-to-black dye composition | |
| CN102516797B (en) | Monoazo dye compound and orange to red dye composition | |
| CN109535769B (en) | Disperse red dye composition and dye product | |
| CN105131648A (en) | Novel composite black disperse dye | |
| CN103382314B (en) | A kind of Dark azo type disperse dye composition | |
| CN105623298A (en) | Orange disperse dye compound and application thereof | |
| CN111117290B (en) | Disperse red dye composition and dye product | |
| CN104884539B (en) | It is a kind of blue to black disperse dye compound and its application |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |