CN105566940A - Phthalimidyl azo dye and preparation method and application thereof - Google Patents
Phthalimidyl azo dye and preparation method and application thereof Download PDFInfo
- Publication number
- CN105566940A CN105566940A CN201610057383.5A CN201610057383A CN105566940A CN 105566940 A CN105566940 A CN 105566940A CN 201610057383 A CN201610057383 A CN 201610057383A CN 105566940 A CN105566940 A CN 105566940A
- Authority
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- China
- Prior art keywords
- formula
- represent
- dye
- azo dye
- phthaloyl
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- 0 CCCCN(C(c(cc1C#N)c2c(C#N)c1N=Nc(c(*)c1)cc(*)c1N(*)*)=O)C2=O Chemical compound CCCCN(C(c(cc1C#N)c2c(C#N)c1N=Nc(c(*)c1)cc(*)c1N(*)*)=O)C2=O 0.000 description 1
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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/40—Preparation of azo dyes from other azo compounds by substituting hetero atoms by radicals containing other hetero atoms
- C09B43/42—Preparation of azo dyes from other azo compounds by substituting hetero atoms by radicals containing other hetero atoms by substituting radicals containing hetero atoms for —CN 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
- C09B29/0029—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing only nitrogen as heteroatom
- C09B29/0033—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing only nitrogen as heteroatom containing a five-membered heterocyclic ring with one nitrogen atom
-
- 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
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0079—Azoic dyestuff preparations
-
- 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
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/008—Preparations of disperse dyes or solvent 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Dispersion Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Coloring (AREA)
Abstract
The invention discloses a phthalimidyl azo dye and a preparation method and application thereof. The structural formula of the phthalimidyl azo dye is shown as a formula I. A coupled component of the phthalimidyl azo dye contains the ester bond structure, therefore, the phthalimidyl azo dye has higher affinity with polyester fibers, solidified dye is not prone to migrate to the surfaces of the fibers from the interiors of the fibers even at high temperature and is not prone to discoloration, the dye is not prone to contaminate other fabrics when ironing is conducted, the dye has excellent thermal migration fastness, sublimation fastness and washing fastness, and therefore the good fastness on resisting rubbing, washing, color bleeding, sweat stains, dry washing and solarization of the fabric is maintained; a methoxy group further exists on the ortho-position of the amino group of the coupled component, the molecular weight of the dye is increased by introducing the methoxy group, and the sublimation fastness of the dye is further improved.
Description
Technical field
The present invention relates to a kind of dispersed blue dye, be specifically related to a kind of phthalic imidine azoic dyestuff and its preparation method and application.
Background technology
After entering 21 century, the competition in world textile market is more and more fierce, and the economy in South East Asia has become the synonym of low cost, high growth, and the textile industry business of Europe, the U.S. etc. is also accelerated to shift to Asia.In order to adapt to the situation of piece market cut-throat competition, making that the production cost of textiles constantly reduces, quality product improves constantly, carrying capacity of environment constantly alleviates, having become the target that textile enterprise is common.
Dispersed dye solubleness in water is very low, and particle is very thin, and in dispersion in dye liquor, belong to nonionic dye, be mainly used in the dyeing of terylene, its dyefastness is higher.Wherein, phthaloyl azo dye is a kind of dispersed blue dye, is that field of textiles dyes to fabric or the necessary product of stamp.
The Chinese patent literature being CN1249171C as Authorization Notice No. discloses a kind of phthaloyl azo dye, and the structural formula of this azoic dyestuff is such as formula shown in (1):
Wherein, R
1represent hydrogen, methyl or-NHCOR
4, R
4represent C
1-C
4alkyl; R
2and R
3separately represent C
1-C
4alkyl, and for this alkyl chain, from C
2above, wherein can insert or not insert Sauerstoffatom.
But existing phthaloyl azo dye all exists the problem of sublimation fastness difference, washing fastness, very easily move out from fabric fibre inside under the high temperature conditions, have a strong impact on the dyefastness of dyestuff to fabric.
Summary of the invention
The invention provides a kind of phthaloyl azo dye, this phthaloyl azo dye solves the problem of phthaloyl azo dye dyefastness difference in prior art.
A kind of phthaloyl azo dye, its structural formula is as shown in formula I:
Wherein, R
1represent C
1~ C
4alkyl or-C
3h
5;
R
2expression-CH
2cOOR
5, R
5represent methyl, ethyl or butyl;
R
3represent hydrogen or methoxyl group;
R
4represent hydrogen, methyl or NHCOR
6, R
6represent C
1~ C
4alkyl.
As do not made specified otherwise, in the present invention, Bu group represents normal-butyl, and Et group represents ethyl, and butyl can be normal-butyl, isobutyl-, sec-butyl or the tertiary butyl;-C
3h
5can be-CH
2-CH=CH
2, also can be-C (CH
3)=CH
2.
Containing ester bond structure (-CH in the coupling component of phthaloyl azo dye of the present invention
2cOOR
5), therefore with trevira, there is stronger avidity, even if the dyestuff of set is at high temperature also not easily from fibrous inside migration to fiber surface, not easily there is look to become, also other fabrics are not easily stain during flatiron, dyestuff is made to have excellent thermal migration and sublimation fastness, thus the rub resistance making fabric keep good, water-fastness, look tears, perspiration resistance, resistance to dry-cleaning and sunlight fastness.
As preferably, the structural formula of described phthaloyl azo dye is such as formula shown in (I-1):
Wherein, R
1represent ethyl or-C
3h
5, R
2expression-CH
2cOOR
5, R
5represent methyl, ethyl or butyl.
There is methoxyl group in the amino ortho position of coupling component of phthaloyl azo dye of the present invention, the introducing of methoxyl group makes the molecular weight of dyestuff increase, and further increases the thermal migration of dyestuff, sublimation fastness and washing fastness.
As preferably, the structural formula of described phthaloyl azo dye is such as formula shown in (I-2), formula (I-3) or formula (I-4):
In formula (I-4), R
5represent ethyl or butyl.
Present invention also offers the preparation method of described phthaloyl azo dye, this preparation method comprises the following steps:
1) by the bromide diazotization shown in formula (1), diazonium salt is obtained;
As preferably, the preparation method of described bromide is: by weight, add 100 parts, water, hydrochloric acid 50 parts, butylimine 21.8 parts in a reservoir, bromine 8 parts is slowly added under stirring, be warming up to 40 ~ 70 DEG C of insulation reaction 1 hour, more slowly add 8 parts of hydrogen peroxide, insulation reaction to terminal, filter washing, obtain the bromide shown in formula (1);
2) by the coupling component coupling shown in diazonium salt and formula (2), the intermediate compound shown in formula (3) is obtained:
Wherein, R
1represent C
1~ C
4alkyl or-C
3h
5;
R
2expression-CH
2cOOR
5, R
5represent methyl, ethyl or butyl;
R
3represent hydrogen or methoxyl group;
R
4represent hydrogen, methyl or NHCOR
6, R
6represent C
1~ C
4alkyl;
3) the Br group in intermediate compound is substituted by cyano group, obtains the phthaloyl azo dye as shown in formula I.
Work as R
4represent NHCOR
6, R
6represent C
1~ C
4during alkyl, step 2) described in the preparation method of coupling combination be:
Utilize 3-amino-4-methoxyacetanilide or 3-amino acetanilide and halogenated alkane to carry out alkylated reaction, obtain the coupling component shown in formula (2-1):
Wherein, R
1represent C
1~ C
4alkyl or-C
3h
5;
R
2expression-CH
2cOOR
5, R
5represent methyl, ethyl or butyl;
R
3represent hydrogen or methoxyl group;
R
4represent NHCOR
6, R
6represent C
1~ C
4alkyl.
The each reaction occurred in above-mentioned preparation method all can adopt method well known to those skilled in the art to go.Based on the sublimation fastness that above-mentioned phthaloyl azo dye is excellent, present invention also offers the application of described phthaloyl azo dye in dyeing polyester fibers; And a kind ofly utilize described phthaloyl azo dye to carry out dyeing or Polyester Fibers that stamp obtains.
Present invention also offers a kind of disperse dye composition, this disperse dye composition contains phthaloyl azo dye of the present invention, and described phthaloyl azo dye is selected from least one compound in general structure (I).
Present invention also offers the application of described disperse dye composition in dyeing polyester fibers; And a kind ofly utilize described disperse dye composition to carry out dyeing or Polyester Fibers that stamp obtains.
Compared with prior art, beneficial effect of the present invention is:
(1) coupling component of phthaloyl azo dye of the present invention is interior containing ester bond structure (-CH
2cOOR
5), therefore with trevira, there is stronger avidity, even if the dyestuff of set is at high temperature also not easily from fibrous inside migration to fiber surface, not easily there is look to become, also other fabrics are not easily stain during flatiron, dyestuff is made to have excellent thermal migration and sublimation fastness, thus the rub resistance making fabric keep good, water-fastness, look tears, perspiration resistance, resistance to dry-cleaning and sunlight fastness.
(2) there is methoxyl group in the amino ortho position of the coupling component of phthaloyl azo dye of the present invention, and the introducing of methoxyl group makes the molecular weight of dyestuff increase, further increase dyestuff, thermal migration, sublimation fastness and washing fastness.
Embodiment
Embodiment is utilized to be described in further detail technical scheme of the present invention below.
Embodiment 1
A kind of phthaloyl azo dye of the present embodiment, its preparation method comprises:
(1) add 100 grams, water, hydrochloric acid 50 grams, butylimine 21.8 grams in a reservoir, slowly add bromine 8 grams under stirring, be warming up to 40-70 DEG C of insulation reaction 1 hour, more slowly add 8 grams of hydrogen peroxide, insulation reaction to terminal, is filtered and is washed to obtain bromide;
(2) get 37.6 grams of bromides to mix with 20 grams, sulfuric acid, be stirred to bromide and dissolve, be then slowly added dropwise to nitrosyl sulfuric acid 33 grams, at 10-35 DEG C, insulation reaction to terminal, obtains diazonium salt;
(3) 3-amino-4-methoxyacetanilide 18 grams, ethanol 120 grams, Sodium Bromide 0.2 gram is added in a reservoir, be warming up to 80-100 DEG C of reaction to terminal, methyl chloroacetate 10.8 grams, triethylamine 10.6 grams is added again after being down to room temperature, be warming up to 70 ~ 80 DEG C of back flow reaction to terminal, filter, filtrate is required coupling component;
(4) in coupling component, add 200 grams, water, 15 grams, sulfuric acid, 300 grams, ice, control temperature slowly adds diazonium salt, terminal to after be warming up to 60-65 DEG C of insulation and filter to obtain BASE in 1 hour;
(5) in 200 grams of DMF, BASE45 gram is added, rising temperature for dissolving, cooling adds copper hydroxide 0.3 gram, zinc cyanide 7.5 grams, be warming up to 100-105 DEG C of insulation reaction 2 hours endpoint detection, terminal to after slowly add 55 grams of water, filter, obtain such as formula the phthaloyl azo dye shown in (I-2):
Embodiment 2
A kind of phthaloyl azo dye of the present embodiment, the preparation method with reference to embodiment 1 obtains such as formula the phthaloyl azo dye shown in (I-3):
Embodiment 3
A kind of phthaloyl azo dye of the present embodiment, the preparation method with reference to embodiment 1 obtains such as formula the phthaloyl azo dye shown in (I-4-1):
Embodiment 4
A kind of phthaloyl azo dye of the present embodiment, the preparation method with reference to embodiment 1 obtains such as formula the phthaloyl azo dye shown in (I-4-2):
Embodiment 5
A kind of phthaloyl azo dye of the present embodiment, the preparation method with reference to embodiment 1 obtains such as formula the phthaloyl azo dye shown in (I-5):
Embodiment 6
A kind of phthaloyl azo dye of the present embodiment, the preparation method with reference to embodiment 1 obtains such as formula the phthaloyl azo dye shown in (I-6):
Embodiment 7 ~ 11
The structural formula of the phthaloyl azo dye of the present embodiment 7 ~ 11 is as shown in table 1:
Table 1 has corresponding R
1, R
2, R
3, R
4the phthaloyl azo dye of group
Embodiment 12
A kind of disperse dye composition of the present embodiment, wherein containing at least one in the phthaloyl azo dye of embodiment 1 ~ 11.
Test example 1
Phthaloyl azo dye embodiment 1 ~ 11 prepared mixes according to the weight ratio of 1:2:5 with Dispersant MF, water respectively, is placed in the shredding unit such as sand mill or shredder and carries out corpusculed, obtains 11 kinds of dye formulations.
11 kinds of dye formulations respectively get 1.0g, be scattered in 500mL water, obtain dispersion liquid, draw 20mL dispersion liquid again to mix with 60mL water, obtain dye liquor, regulate dye bath pH to be 5 with acetic acid, put into 4g trevira when being warming up to 70 DEG C to dye, and with 30min in dye bath temperature is warming up to 130 DEG C from 70 DEG C, be cooled to 90 DEG C be incubated 30min at 130 DEG C after, take out Final finishing post-drying.Observe sample cloth coloured light, and the ISO-105-P01 that adopts international standards tests every fastness of cloth specimen, with Authorization Notice No. disclosed in the Chinese patent literature of CN1249171C phthaloyl azo dye in contrast, test result is in table 2.
Sublimation fastness and the washing fastness of each phthaloyl azo dye of table 2 compare
| Phthaloyl azo dye | Sublimation fastness (level) | Washing fastness (level) |
| Embodiment 1 | 7 | 5 |
| Embodiment 2 | 7 | 5 |
| Embodiment 3 | 7 | 5 |
| Embodiment 4 | 7 | 5 |
| Embodiment 5 | 7 | 5 |
| Embodiment 6 | 7 | 5 |
| Embodiment 7 | 6-7 | 5 |
| Embodiment 8 | 6-7 | 5 |
| Embodiment 9 | 6-7 | 5 |
| Embodiment 10 | 7 | 5 |
| Embodiment 11 | 6-7 | 5 |
| Contrast | 6 | 4 |
From table 2, compared with the control, the phthaloyl azo dye of embodiment 1 ~ 11 (especially embodiment 1 ~ 6) is because having excellent thermal migration and sublimation fastness, the washing fastness of fabric is significantly improved, other dyefastness, as rub resistance, look tears, perspiration resistance, resistance to dry-cleaning and sunlight fastness also remain on preferably level.
Claims (9)
1. a phthalic imidine azoic dyestuff, is characterized in that, structural formula is as shown in formula I:
Wherein, R
1represent C
1~ C
4alkyl or-C
3h
5;
R
2expression-CH
2cOOR
5, R
5represent methyl, ethyl or butyl;
R
3represent hydrogen or methoxyl group;
R
4represent hydrogen, methyl or NHCOR
6, R
6represent C
1~ C
4alkyl.
2. phthalic imidine azoic dyestuff as claimed in claim 1, it is characterized in that, structural formula is such as formula shown in (I-1):
Wherein, R
1represent ethyl or-C
3h
5, R
2expression-CH
2cOOR
5, R
5represent methyl, ethyl or butyl.
3. phthalic imidine azoic dyestuff as claimed in claim 2, it is characterized in that, structural formula is such as formula shown in (I-2), formula (I-3) or formula (I-4):
In formula (I-4), R
5represent ethyl or butyl.
4. the preparation method of phthalic imidine azoic dyestuff as claimed in claim 1, is characterized in that, comprise the following steps:
1) by the bromide diazotization shown in formula (1), diazonium salt is obtained;
2) by the coupling component coupling shown in diazonium salt and formula (2), the intermediate compound shown in formula (3) is obtained:
Wherein, R
1represent C
1~ C
4alkyl or-C
3h
5;
R
2expression-CH
2cOOR
5, R
5represent methyl, ethyl or butyl;
R
3represent hydrogen or methoxyl group;
R
4represent hydrogen, methyl or NHCOR
6, R
6represent C
1~ C
4alkyl;
3) the Br group in intermediate compound is substituted by cyano group, obtains the phthaloyl azo dye as shown in formula I.
5. a disperse dye composition, is characterized in that, containing, for example the arbitrary described phthalimide azoic dyestuff of claims 1 to 3, described phthalic imidine azoic dyestuff is selected from least one compound in general structure (I).
6. the application of phthalic imidine azoic dyestuff in dyeing polyester fibers or stamp as described in as arbitrary in claims 1 to 3.
7. the application of disperse dye composition in dyeing polyester fibers or stamp as claimed in claim 5.
8. one kind utilizes described phthalic imidine azoic dyestuff as arbitrary in claims 1 to 3 to carry out dyeing or the Polyester Fibers of stamp acquisition.
9. one kind utilizes disperse dye composition as claimed in claim 5 to carry out the Polyester Fibers dyeed or stamp obtains.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610057383.5A CN105566940A (en) | 2016-01-27 | 2016-01-27 | Phthalimidyl azo dye and preparation method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610057383.5A CN105566940A (en) | 2016-01-27 | 2016-01-27 | Phthalimidyl azo dye and preparation method and application thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN105566940A true CN105566940A (en) | 2016-05-11 |
Family
ID=55877604
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610057383.5A Pending CN105566940A (en) | 2016-01-27 | 2016-01-27 | Phthalimidyl azo dye and preparation method and application thereof |
Country Status (1)
| Country | Link |
|---|---|
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107011700A (en) * | 2017-05-02 | 2017-08-04 | 杭州福莱蒽特精细化工有限公司 | A kind of dispersed black dye mixture of high dyefastness |
| CN107722663A (en) * | 2017-10-10 | 2018-02-23 | 浙江万丰化工有限公司 | A kind of azo dyes compounds and its preparation method and application |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1331730A (en) * | 1998-12-31 | 2002-01-16 | 西巴特殊化学品控股有限公司 | Phthalimidyl azo pigments, method for producing same and utilisation thereof |
| WO2010046192A2 (en) * | 2008-10-21 | 2010-04-29 | Huntsman Advanced Materials (Switzerland) Gmbh | Azo dyes, a process for the preparation thereof and the use thereof |
| KR20130069162A (en) * | 2011-12-16 | 2013-06-26 | 대영산업 주식회사 | Disperse dye for polylactic acid fibers and black dye composition comprising thereof |
| CN104448892A (en) * | 2014-11-18 | 2015-03-25 | 李百春 | Sapphire-blue disperse dye with high washing fastness and sublimation fastness and preparation method thereof |
-
2016
- 2016-01-27 CN CN201610057383.5A patent/CN105566940A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1331730A (en) * | 1998-12-31 | 2002-01-16 | 西巴特殊化学品控股有限公司 | Phthalimidyl azo pigments, method for producing same and utilisation thereof |
| WO2010046192A2 (en) * | 2008-10-21 | 2010-04-29 | Huntsman Advanced Materials (Switzerland) Gmbh | Azo dyes, a process for the preparation thereof and the use thereof |
| KR20130069162A (en) * | 2011-12-16 | 2013-06-26 | 대영산업 주식회사 | Disperse dye for polylactic acid fibers and black dye composition comprising thereof |
| CN104448892A (en) * | 2014-11-18 | 2015-03-25 | 李百春 | Sapphire-blue disperse dye with high washing fastness and sublimation fastness and preparation method thereof |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107011700A (en) * | 2017-05-02 | 2017-08-04 | 杭州福莱蒽特精细化工有限公司 | A kind of dispersed black dye mixture of high dyefastness |
| CN107722663A (en) * | 2017-10-10 | 2018-02-23 | 浙江万丰化工有限公司 | A kind of azo dyes compounds and its preparation method and application |
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