CN1869004A - Monoazo compound, preparation method and application thereof - Google Patents
Monoazo compound, preparation method and application thereof Download PDFInfo
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- CN1869004A CN1869004A CN 200510049819 CN200510049819A CN1869004A CN 1869004 A CN1869004 A CN 1869004A CN 200510049819 CN200510049819 CN 200510049819 CN 200510049819 A CN200510049819 A CN 200510049819A CN 1869004 A CN1869004 A CN 1869004A
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- Prior art keywords
- monoazo compound
- preparation
- sulfuric acid
- disperse yellow
- compound
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- -1 Monoazo compound Chemical class 0.000 title claims abstract description 24
- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- VGKYEIFFSOPYEW-UHFFFAOYSA-N 2-methyl-4-[(4-phenyldiazenylphenyl)diazenyl]phenol Chemical compound Cc1cc(ccc1O)N=Nc1ccc(cc1)N=Nc1ccccc1 VGKYEIFFSOPYEW-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000001043 yellow dye Substances 0.000 claims abstract description 16
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000012954 diazonium Substances 0.000 claims abstract description 12
- 150000001989 diazonium salts Chemical class 0.000 claims abstract description 10
- 238000005859 coupling reaction Methods 0.000 claims abstract description 8
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229960005081 diclofenamide Drugs 0.000 claims description 12
- 239000000843 powder Substances 0.000 claims description 12
- 238000004043 dyeing Methods 0.000 claims description 9
- 238000006193 diazotization reaction Methods 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 5
- 229920004935 Trevira® Polymers 0.000 claims description 4
- 238000000967 suction filtration Methods 0.000 claims description 4
- GJQPMPFPNINLKP-UHFFFAOYSA-N diclofenamide Chemical compound NS(=O)(=O)C1=CC(Cl)=C(Cl)C(S(N)(=O)=O)=C1 GJQPMPFPNINLKP-UHFFFAOYSA-N 0.000 claims description 3
- 230000008878 coupling Effects 0.000 claims description 2
- 238000010168 coupling process Methods 0.000 claims description 2
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 claims 1
- 239000000975 dye Substances 0.000 abstract description 7
- RTZYVAQWQXPIAC-UHFFFAOYSA-N 4-[(4-phenyldiazenylphenyl)diazenyl]phenol Chemical compound C1=CC(O)=CC=C1N=NC1=CC=C(N=NC=2C=CC=CC=2)C=C1 RTZYVAQWQXPIAC-UHFFFAOYSA-N 0.000 abstract description 5
- ZTTPWPKJVSSSMW-UHFFFAOYSA-N 3-(n-benzylanilino)propanenitrile Chemical compound C=1C=CC=CC=1N(CCC#N)CC1=CC=CC=C1 ZTTPWPKJVSSSMW-UHFFFAOYSA-N 0.000 abstract 1
- DADSZOFTIIETSV-UHFFFAOYSA-N n,n-dichloroaniline Chemical compound ClN(Cl)C1=CC=CC=C1 DADSZOFTIIETSV-UHFFFAOYSA-N 0.000 abstract 1
- 238000000034 method Methods 0.000 description 9
- 239000002270 dispersing agent Substances 0.000 description 7
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- 230000007613 environmental effect Effects 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 229920001732 Lignosulfonate Polymers 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000012752 auxiliary agent Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- NVVZQXQBYZPMLJ-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 NVVZQXQBYZPMLJ-UHFFFAOYSA-N 0.000 description 2
- 235000019357 lignosulphonate Nutrition 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000000859 sublimation Methods 0.000 description 2
- 230000008022 sublimation Effects 0.000 description 2
- MHXFWEJMQVIWDH-UHFFFAOYSA-N 1-amino-4-hydroxy-2-phenoxyanthracene-9,10-dione Chemical compound C1=C(O)C=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C1OC1=CC=CC=C1 MHXFWEJMQVIWDH-UHFFFAOYSA-N 0.000 description 1
- WODGMMJHSAKKNF-UHFFFAOYSA-N 2-methylnaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(C)=CC=C21 WODGMMJHSAKKNF-UHFFFAOYSA-N 0.000 description 1
- AIARLPIXVMHZLJ-UHFFFAOYSA-N 4,8-diamino-2-bromo-1,5-dihydroxyanthracene-9,10-dione Chemical compound O=C1C2=C(N)C=C(Br)C(O)=C2C(=O)C2=C1C(O)=CC=C2N AIARLPIXVMHZLJ-UHFFFAOYSA-N 0.000 description 1
- SRDOTWUOTQTGAK-UHFFFAOYSA-N C=O.C1(=CC=CC2=CC=CC=C12)S(=O)(=O)OCC1=CC=CC=C1 Chemical compound C=O.C1(=CC=CC2=CC=CC=C12)S(=O)(=O)OCC1=CC=CC=C1 SRDOTWUOTQTGAK-UHFFFAOYSA-N 0.000 description 1
- 229920004934 Dacron® Polymers 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 238000010009 beating Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
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Abstract
The invention relates to a monoazo compound, a preparation method and application thereof. The monoazo compound is shown as a formula , and the preparation method comprises the following steps: after dichloroaniline and nitrosyl sulfuric acid are diazotized in sulfuric acid, the obtained diazonium salt and N-cyanoethyl-N-benzyl aniline are subjected to coupling reaction, and paste is obtained after post-treatment, namely the product. The monoazo compound provided by the invention is used for disperse yellow dye, has good color fastness and is safe, and is an ideal environment-friendly dye capable of effectively replacing C.I. disperse yellow 23.
Description
(1) technical field
The present invention relates to a kind of Monoazo compound, preparation method and its usage.
(2) background technology
As everyone knows, Disperse Yellow RGFL (C.I. DISPERSE YELLOW 23) is a very important dispersed dye kind, although its synthesis technique is simple, but when being applied to trevira dyeing, can obtain good dyeing behavior, can reach 6 grades as sun-resistant fastness, anti-ly soap 4～5 grades, good level-dyeing property.In addition, Disperse Yellow RGFL also can be formed the fabulous low temperature three primary colors of compatibleness with C.I. disperse red 60 and C.I. Disperse Blue-56.Yet, because easily decomposing under given conditions, Disperse Yellow RGFL produces carcinogenic aromatic amine, can not satisfy the environmental requirement of increasingly stringent.
(3) summary of the invention
The object of the invention is to provide a kind of Monoazo compound, preparation method and as the purposes of disperse yellow dye.
Described Monoazo compound is suc as formula shown in (I),
The preferred compound structure of the present invention is as (II) or (III):
A kind of preparation method of described Monoazo compound comprises: dichlorphenamide bulk powder and nitrosyl sulfuric acid are carried out diazotization in sulfuric acid after, gained diazonium salt and N-cyanoethyl-Phenhenzamine carry out coupled reaction, and aftertreatment gets paste and is described product.
Described diazotization temperature is preferably 15-20 ℃.
Described coupled reaction temperature is preferably 15-25 ℃.
The preparation method of described Monoazo compound, recommend to carry out as follows:
With 3, the 4-dichlorphenamide bulk powder carries out diazotization with nitrosyl sulfuric acid in sulfuric acid medium, and the diazonium salt that obtains and N-cyanoethyl-Phenhenzamine be 20 ℃ of couplings, insulated and stirred 40 minutes, suction filtration also is washed to neutrality, paste be described product.
Described Monoazo compound can be used as disperse yellow dye, especially is used as the dyeing of trevira.When dyeing as disperse yellow dye, described Monoazo compound often with the certain proportion of auxiliary agent compounding.Described auxiliary agent can be one of following or its any blended usual auxiliaries: naphthalene sulfonic acidformaldehyde condensation product, alkyl naphthalene sulfonic acid formaldehyde condensation products, sulfonated lignin.Described naphthalenesulfonateformaldehyde formaldehyde condensation such as dispersing agent NNO; Alkyl naphthalene sulfonic acid formaldehyde condensation products such as Dispersant MF (condensation compound of methyl naphthalene sulfonic acid and formaldehyde), dispersing agent CNF (benzyl naphthalenesulfonate formaldehyde condensation compound) etc.; Sulfonated lignin such as sodium lignosulfonate (commercial dispersants Reax83A, Reax85A) etc.
It is good that Monoazo compound of the present invention is used for the disperse yellow dye dyefastness, and safety is a kind of environmental protection type dye that can effectively substitute C.I. DISPERSE YELLOW 23 ideally.
(4) embodiment
With specific embodiment the present invention is described below, but protection scope of the present invention is not limited to this.
Embodiment 1
1. diazotization
In the there-necked flask of 150ml, slowly add sulfuric acid, nitrosyl sulfuric acid, the outside lowers the temperature with water-bath, and controlled temperature is about 15-20 ℃.Add 3 after stirring 0.5hr, 4-dichlorphenamide bulk powder 20 grams, add fashionable should not be too fast, should control certain feed rate, to prevent the material caking, the whole reinforced time is controlled to be 1.5hr, stir 3hr after adding, the detection reaction terminal point (1. diazonium salt can be in frozen water clear; 2. diazonium salt can make starch potassium iodide paper become blue), make 3,4-dichlorphenamide bulk powder diazonium salt is standby.
2. coupled reaction
In the beaker of 1000ml, add raw spirit 200ml, add N-cyanoethyl-Phenhenzamine 28 grams, emulsifying agent TX-15 1.2 grams, making beating 3hr adds thionamic acid 1.5 grams, and controlled temperature drips diazonium liquid about 20 ℃, the dropping time is 1.5hr, at 20 ℃ of stirring reaction 12hr, measured reaction terminal point (checking that with oozing the circle method diazonium salt is excessive slightly) continued insulated and stirred 40 minutes, suction filtration also is washed to neutrality, gets paste and is described product.
The paste and the Dispersant MF that obtain are ground in 1: 1.8 ratio, spray-driedly then obtain disperse yellow dye of the present invention.
The dyeing experiment
Getting the above-mentioned dispersed dye that make of 0.5 gram is dispersed in 500 ml waters, mix with 60 milliliters water after drawing 20 milliliters, transferring dye bath pH with acetic acid is 5, be warming up to 70 ℃ put into simultaneously 2 the gram woven dacrons dye, in 30 minutes, be warmed up to 130 ℃ by 70 ℃, be incubated 30 minutes, be cooled to begin below 90 ℃ the sampling.Observe its color, adopt GB GB/T3921-1997, GB/T3920-1997, GB/T5718-1997 to test its water-fast colour fastness, colour fastness to rubbing, color fastness to sublimation washed respectively, test result sees Table 1.
Embodiment 2
In the beaker of 1000ml, add DMF 200ml, add N-cyanoethyl-Phenhenzamine 28 grams, stirring makes it dissolving, adds thionamic acid 1.5 grams, and controlled temperature drips embodiment 1 and makes diazonium liquid about 20 ℃, the dropping time is 1.5hr, at 20 ℃ of stirring reaction 12hr, measured reaction terminal point (checking that with oozing the circle method diazonium salt is excessive slightly) continued insulated and stirred 40 minutes, suction filtration also is washed to neutrality, gets paste and is described product.
The paste and the dispersing agent CNF that obtain are ground in 1: 2 ratio, spray-driedly then obtain disperse yellow dye of the present invention.
According to each dyefastness of embodiment 1 described method test disperse yellow dye, test result sees Table 1.
Embodiment 3
With 2, the 3-dichlorphenamide bulk powder substitutes 3, and the 4-dichlorphenamide bulk powder can obtain disperse yellow dye of the present invention according to the method preparation of embodiment 1.
According to each dyefastness of embodiment 1 described method test disperse yellow dye, test result sees Table 1.
Embodiment 4
Substitute 3 with mixed dichlorphenamide bulk powder (wherein, 3,4-dichlorphenamide bulk powder, 2, the weight percentage of 3-dichlorphenamide bulk powder is respectively 81.5%, 18.5%), the 4-dichlorphenamide bulk powder can obtain disperse yellow dye of the present invention according to the method preparation of embodiment 1.
According to each dyefastness of embodiment 1 described method test disperse yellow dye, test result sees Table 1.
Embodiment 5
Monoazo compound 75g, the Monoazo compound 25g that embodiment 3 makes that embodiment 1 is made add 100g water, the grinding of 200g Dispersant MF, and spraying drying makes disperse yellow dye of the present invention again.
According to each dyefastness of embodiment 1 described method test disperse yellow dye, test result sees Table 1.
Comparative Examples 1
Get 0.5 gram C.I. DISPERSE YELLOW, 23 dyestuffs and repeat above-mentioned dyeing experiment.Test result sees Table 1.
Table 1
| The embodiment title | Color | Washing fastness | Crock fastness | 180 ℃ of sublimation fastness |
| Embodiment 1 | Golden yellow | 4～5 grades | 4～5 grades | 4～5 grades |
| Embodiment 2 | Golden yellow | 4～5 grades | 4～5 grades | 4～5 grades |
| Embodiment 3 | Golden yellow | 4～5 grades | 4～5 grades | 4～5 grades |
| Embodiment 4 | Golden yellow | 4～5 grades | 4～5 grades | 4～5 grades |
| Embodiment 5 | Golden yellow | 4～5 grades | 4～5 grades | 4～5 grades |
| Comparative Examples 1 | Golden yellow | 4 grades | 4～5 grades | 4 grades |
As seen, disperse yellow dye of the present invention can obtain and the very proximate coloured light of C.I. DISPERSE YELLOW 23 being applied to trevira when dyeing, and the fastness index also exceeds half grade, is the ideal environmental protection type dye of an alternative C.I. DISPERSE YELLOW 23.
Claims (9)
1, a kind of Monoazo compound suc as formula (I),
2, Monoazo compound as claimed in claim 1 is characterized in that structure shown in (II),
3, Monoazo compound as claimed in claim 1 is characterized in that structure shown in (III),
4, the preparation method of the described compound of a kind of claim 1 comprises: dichlorphenamide bulk powder and nitrosyl sulfuric acid are carried out diazotization in sulfuric acid after, gained diazonium salt and N-cyanoethyl-Phenhenzamine carry out coupled reaction, and aftertreatment gets paste and is described product.
5, as the preparation method of Monoazo compound as described in the claim 4, it is characterized in that described diazotization temperature is 15-20 ℃.
6, as the preparation method of Monoazo compound as described in the claim 4, it is characterized in that described coupled reaction temperature is 15-25 ℃.
7, as the preparation method of Monoazo compound as described in the claim 6, it is characterized in that comprising the steps: with 3, the 4-dichlorphenamide bulk powder carries out diazotization with nitrosyl sulfuric acid in sulfuric acid medium, the diazonium salt that obtains and N-cyanoethyl-Phenhenzamine are 20 ℃ of couplings, insulated and stirred 40 minutes, suction filtration also is washed to neutrality, gets paste and is described product.
8, the described Monoazo compound of claim 1 is as the purposes of disperse yellow dye.
9, purposes as claimed in claim 8 is characterized in that the dyeing of described Monoazo compound as trevira.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2005100498198A CN100503556C (en) | 2005-05-24 | 2005-05-24 | Monoazo disperse yellow dye, preparation method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2005100498198A CN100503556C (en) | 2005-05-24 | 2005-05-24 | Monoazo disperse yellow dye, preparation method and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1869004A true CN1869004A (en) | 2006-11-29 |
| CN100503556C CN100503556C (en) | 2009-06-24 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB2005100498198A Expired - Fee Related CN100503556C (en) | 2005-05-24 | 2005-05-24 | Monoazo disperse yellow dye, preparation method and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN100503556C (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101117446B (en) * | 2007-07-24 | 2011-07-06 | 上虞市金冠化工有限公司 | Process for synthesizing azo dispersion dyes monomer compound |
| CN101215245B (en) * | 2007-01-05 | 2011-11-30 | 浙江龙盛集团股份有限公司 | Monoazo compound containing diester and its preparation, application and dye composition |
| CN102964221A (en) * | 2012-11-26 | 2013-03-13 | 江苏扬农化工股份有限公司 | Clean production process of dicamba synthesis midbody |
| CN104327548A (en) * | 2014-10-08 | 2015-02-04 | 浙江龙盛集团股份有限公司 | Disperse yellow and disperse orange dye composition |
| CN104557473A (en) * | 2015-01-09 | 2015-04-29 | 山东潍坊润丰化工股份有限公司 | Method for producing halogenated phenylamine from halogenated aniline through diazotization |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4039524A (en) * | 1972-12-27 | 1977-08-02 | Gaf Corporation | Keto-amido containing phenylazo benzothiazole dyestuffs |
| US4140683A (en) * | 1976-02-23 | 1979-02-20 | Eastman Kodak Company | Dyes from thienylazo compounds and cyclohexylaminoacylanilide couplers |
| JPH0745636B2 (en) * | 1991-06-18 | 1995-05-17 | 三菱化成ヘキスト株式会社 | Disperse dye mixture |
-
2005
- 2005-05-24 CN CNB2005100498198A patent/CN100503556C/en not_active Expired - Fee Related
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101215245B (en) * | 2007-01-05 | 2011-11-30 | 浙江龙盛集团股份有限公司 | Monoazo compound containing diester and its preparation, application and dye composition |
| CN101117446B (en) * | 2007-07-24 | 2011-07-06 | 上虞市金冠化工有限公司 | Process for synthesizing azo dispersion dyes monomer compound |
| CN102964221A (en) * | 2012-11-26 | 2013-03-13 | 江苏扬农化工股份有限公司 | Clean production process of dicamba synthesis midbody |
| CN102964221B (en) * | 2012-11-26 | 2014-07-09 | 江苏优嘉化学有限公司 | Clean production process of dicamba synthesis midbody |
| CN104327548A (en) * | 2014-10-08 | 2015-02-04 | 浙江龙盛集团股份有限公司 | Disperse yellow and disperse orange dye composition |
| CN104327548B (en) * | 2014-10-08 | 2016-08-10 | 浙江龙盛集团股份有限公司 | A kind of disperse yellow is to orange compositions |
| CN104557473A (en) * | 2015-01-09 | 2015-04-29 | 山东潍坊润丰化工股份有限公司 | Method for producing halogenated phenylamine from halogenated aniline through diazotization |
Also Published As
| Publication number | Publication date |
|---|---|
| CN100503556C (en) | 2009-06-24 |
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