CN1108348C - Reactive azo orange dye and its preparing process - Google Patents
Reactive azo orange dye and its preparing process Download PDFInfo
- Publication number
- CN1108348C CN1108348C CN00119056A CN00119056A CN1108348C CN 1108348 C CN1108348 C CN 1108348C CN 00119056 A CN00119056 A CN 00119056A CN 00119056 A CN00119056 A CN 00119056A CN 1108348 C CN1108348 C CN 1108348C
- Authority
- CN
- China
- Prior art keywords
- dye
- sulfuric ester
- reactive
- orange dye
- reactive azo
- 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.)
- Expired - Lifetime
Links
- 239000001048 orange dye Substances 0.000 title claims description 10
- 238000000034 method Methods 0.000 title description 11
- 239000000975 dye Substances 0.000 claims abstract description 28
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 claims abstract description 13
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims abstract description 12
- 150000002148 esters Chemical class 0.000 claims abstract description 9
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 6
- KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims abstract description 4
- 239000012954 diazonium Substances 0.000 claims abstract description 3
- 150000001989 diazonium salts Chemical class 0.000 claims abstract description 3
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 claims abstract 2
- 238000010168 coupling process Methods 0.000 claims description 16
- 230000008878 coupling Effects 0.000 claims description 15
- 238000005859 coupling reaction Methods 0.000 claims description 15
- -1 methoxyl group Chemical group 0.000 claims description 8
- 238000009833 condensation Methods 0.000 claims description 5
- 230000005494 condensation Effects 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- 238000010189 synthetic method Methods 0.000 claims 3
- 238000004043 dyeing Methods 0.000 abstract description 4
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 229920000742 Cotton Polymers 0.000 abstract 1
- 239000000987 azo dye Substances 0.000 abstract 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 6
- 238000006193 diazotization reaction Methods 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 4
- 150000003841 chloride salts Chemical class 0.000 description 3
- 239000000985 reactive dye Substances 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 2
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical class NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 description 1
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- HFIYIRIMGZMCPC-UHFFFAOYSA-J chembl1326377 Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]S(=O)(=O)C1=CC2=CC(S([O-])(=O)=O)=C(N=NC=3C=CC(=CC=3)S(=O)(=O)CCOS([O-])(=O)=O)C(O)=C2C(N)=C1N=NC1=CC=C(S(=O)(=O)CCOS([O-])(=O)=O)C=C1 HFIYIRIMGZMCPC-UHFFFAOYSA-J 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000004045 reactive dyeing Methods 0.000 description 1
- 230000005477 standard model Effects 0.000 description 1
- 229950000244 sulfanilic acid Drugs 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
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- Coloring (AREA)
Abstract
The present invention relates to an orange reactive azo dye which has a structural formula disclosed in the specification. In the structure of the dye, X is a base group which can be converted into ethenyl, R-is a sulfo group and divinyl sulphone sulfuric ester, R1 and R2 are H, Me, Et, OMe and OEt, and M is Na and K. The dye can be not only a simple compound but also various mixtures. Cyanuric chloride is respectively condensed with a compound which contains a sulfo group or divinyl sulphone sulfuric ester aniline, and J acid; then, a condensed product is coupled with diazonium salt which contains a compound converted into the ethenyl. The dye is suitable for dyeing and printing cotton fiber. The dye has the good firmness. The dye is especially matched with reactive black KN-B, and firm black is obtained.
Description
The present invention relates to a kind of reactive azo orange dye and preparation thereof
Korea S reason standing grain company took the lead in having synthesized the orange Vinyl-Sulfone Type dyestuff with two different activities bases in 1985, pieced together the pitch black degree that has improved the black vinyl-sulfone reactive dyes in the C.I. reactive black 5 (reactive black KN-B) greatly, and its structural formula is as follows:
These dyeing level-dyeing property existing problems are if misoperation can produce color spot and color dot, because the bath guards escorting prisoners of this dyestuff belongs to X type reactive dyestuffs, the performance less stable.
The purpose of this invention is to provide have stable performance, a kind of reactive azo orange dye and preparation method that dyefastness is high.
In order to achieve the above object, the structural formula of a kind of reactive azo orange dye of the present invention is as follows:
(1), X is for transforming the gene of vinyl;
(2), R=sulfonic group, vinyl sulfone(Remzaol sulfuric ester;
(3)、R1，R2，＝H、Me、Et、OMe、OEt，M＝Na、K
Wherein Me is that methyl, Et are that ethyl, OMe are that methoxyl group, OEt are oxyethyl group.
R of the present invention can be aminocompound and the J acid condensation that vinyl sulfone(Remzaol sulfuric ester and sulfonic mixture also can be vinyl sulfone(Remzaol sulfuric ester or sulfo group acid, is converted into the diazonium salt of aniline compound of vinyl groups and condenses coupling and makes.
The coupling temperature of the present invention's preparation is 0-85 ℃, PH=3-4 during coupling.
The present invention is in the coupling process, and the azo-group that obtains 3%-5% T=0 ℃ of following coupling is at the isomer of-OH contraposition, and T=85 ℃ of following coupling obtain 27-30%-the OH para-isomeride.The dyestuff that the dyestuff that obtains 85 ℃ of following couplings obtains in 0 ℃ of coupling the good stability of pH value.
A kind of reactive azo orange dye of the present invention is compared with the orange Vinyl-Sulfone Type dyestuff with two different activities bases of Korea S reason standing grain company, stable performance, dyefastness all is better than the orange Vinyl-Sulfone Type dyestuff of Korea S reason standing grain company, and its simultaneous test data are listed in the table one.
In the test process of table one performance index, adopted following standard:
The general condition regulation that the GB2374-1994 dyeing is measured
The measuring method of GB2381-1980 dyestuff insolubles content
The measuring method of GB2386-1980 dye well dyestuff intermediate moisture content
The measuring method of GB2387-1980 reactive dyeing coloured light and intensity
The measuring method of GB2388-1980 printing with reactive dye coloured light and intensity
The measuring method of hydrolised dye and standard model relative content in the GB2389-1980 reactive dyestuffs
The measuring method of GB2390-1980 reactive dyestuffs pH value
The measuring method of GB2391-1980 reactive dyestuffs dye uptake and degree of fixation
The measuring method of GB2392-1980 reactive dyestuffs thermostability
The measuring method of GB2393-1980 printing with reactive dye degree of fixation
Embodiment one: take by weighing 19 parts of weight cyanuric chlorides successively with 28.1 parts of right-(β hydroxyalkyl vinyl sulfone sulfate) aniline, 23.9 parts of sour condensations, then with 28.1 parts of right-(β hydroxyalkyl vinyl sulfone sulfate) aniline diazotization, under 0-5 ℃, the condition of PH=3.5 with
The condenses coupling obtains a kind of gold-tinted orange dyestuff.
Embodiment two: after adopting embodiment one prescription to carry out diazotization, with the condenses coupling, obtain a kind of ruddiness orange dyestuff under 85 ℃, the condition of PH=3.5.
Embodiment three: after adopting embodiment one prescription to carry out diazotization, with the condenses coupling, obtain a kind of than embodiment Erhuang but the orange dye redder than embodiment one under 40 ℃, the condition of PH=3.5.
Implement four: take by weighing 19 parts of weight cyanuric chlorides successively with 17.3 parts of m-sulfanilic acids, 23.9 parts of J acid condensations, then with 28.1 parts of right-(β hydroxyalkyl vinyl sulfone sulfate) aniline diazotization, 0 ℃, PH=3.5 and
Coupling obtains ruddiness orange dyestuff.
Embodiment five: take by weighing 19 parts of weight cyanuric chlorides successively with 17.3 parts of Sulphanilic Acid, 23.9 parts of J acid condensations, then with 28.1 parts of right-(β hydroxyalkyl vinyl sulfone sulfate) aniline diazotization, 0 ℃, PH=3.5 and
Coupling obtains ruddiness orange dyestuff.
Embodiment six: with the dyestuff of embodiment 1 gained and reactive black KN-B by weight the ratio of 20-25:80-75 mix to piece together and obtain good black dyes.
Embodiment seven: dyestuff that embodiment one, embodiment three, embodiment four are obtained and reactive black KN-B be 10-15: 5-2.5: 5-2.5 by weight: 80 ratio is mixed to piece together and is obtained good black dyes, the strength ratio embodiment six high 15-20% of this dyestuff.
Table one
Claims (6)
1, a kind of reactive azo orange dye, its structure is as follows:
(1), X is for being converted into the group of vinyl;
(2), R=sulfonic group, vinyl sulfone(Remzaol sulfuric ester;
(3)R1，R2＝H、Me、Et、OMe、OEt、M＝Na、K，
Wherein Me is that methyl, Et are that ethyl, OMe are that methoxyl group, OEt are oxyethyl group.
2, a kind of reactive azo orange dye according to claim 1 is characterized in that R is vinyl sulfone(Remzaol sulfuric ester and sulfonic mixture.
3, a kind of reactive azo orange dye according to claim 1 is characterized in that R is the vinyl sulfone(Remzaol sulfuric ester.
4, dyestuff according to claim 1, it is characterized in that its synthetic method with cyanuric chloride successively with contain vinyl sulfone(Remzaol sulfuric ester or sulfonic aminocompound and J acid condensation, be converted into the diazonium salt of aniline compound of vinyl groups and condenses coupling and make.
5, dyestuff according to claim 4 is characterized in that its synthetic method coupling temperature is 0-85 ℃.
6, a kind of dyestuff according to claim 4, PH=3-4 when it is characterized in that its synthetic method coupling.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN00119056A CN1108348C (en) | 2000-10-24 | 2000-10-24 | Reactive azo orange dye and its preparing process |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN00119056A CN1108348C (en) | 2000-10-24 | 2000-10-24 | Reactive azo orange dye and its preparing process |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1289804A CN1289804A (en) | 2001-04-04 |
| CN1108348C true CN1108348C (en) | 2003-05-14 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN00119056A Expired - Lifetime CN1108348C (en) | 2000-10-24 | 2000-10-24 | Reactive azo orange dye and its preparing process |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1108348C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100349989C (en) * | 2005-10-27 | 2007-11-21 | 吴江桃源染料厂 | Preparation technology of azo active dyestuff |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101481534B (en) * | 2008-12-12 | 2013-03-20 | 天津德凯化工股份有限公司 | Preparation of reactive dye brilliant blue KN-R |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1182759A (en) * | 1997-11-10 | 1998-05-27 | 华东理工大学 | Reactive dye with diethylene sulfone type group and dichromogen and synthetic method thereof |
-
2000
- 2000-10-24 CN CN00119056A patent/CN1108348C/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1182759A (en) * | 1997-11-10 | 1998-05-27 | 华东理工大学 | Reactive dye with diethylene sulfone type group and dichromogen and synthetic method thereof |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100349989C (en) * | 2005-10-27 | 2007-11-21 | 吴江桃源染料厂 | Preparation technology of azo active dyestuff |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1289804A (en) | 2001-04-04 |
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| Date | Code | Title | Description |
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| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C06 | Publication | ||
| PB01 | Publication | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| EE01 | Entry into force of recordation of patent licensing contract |
Assignee: TAIXING JINYUN DYE CO.,LTD. Assignor: Taixing Jinji Dyestuff Co.,Ltd. Contract record no.: 2010320001255 Denomination of invention: Reactive azo orange dye and its preparing process Granted publication date: 20030514 License type: Exclusive License Open date: 20010404 Record date: 20101229 |
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| CP01 | Change in the name or title of a patent holder |
Address after: 10 No. 225404, Xingang Road, Taixing Economic Development Zone, Jiangsu Patentee after: Jiangsu golden pheasant industrial Limited by Share Ltd. Address before: 10 No. 225404, Xingang Road, Taixing Economic Development Zone, Jiangsu Patentee before: Taixing Jinji Dyestuff Co.,Ltd. |
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| CP01 | Change in the name or title of a patent holder | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20170811 Address after: 225404 No. 10, Xingang Road, Taixing Economic Development Zone, Jiangsu, Taizhou Patentee after: TAIXING JINYUN DYE CO.,LTD. Address before: 10 No. 225404, Xingang Road, Taixing Economic Development Zone, Jiangsu Patentee before: Jiangsu golden pheasant industrial Limited by Share Ltd. |
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| TR01 | Transfer of patent right | ||
| CX01 | Expiry of patent term | ||
| CX01 | Expiry of patent term |
Granted publication date: 20030514 |