CN101250332A - Reactive golden yellow RNL diazo dyes and preparation method thereof - Google Patents
Reactive golden yellow RNL diazo dyes and preparation method thereof Download PDFInfo
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- CN101250332A CN101250332A CNA2008100232982A CN200810023298A CN101250332A CN 101250332 A CN101250332 A CN 101250332A CN A2008100232982 A CNA2008100232982 A CN A2008100232982A CN 200810023298 A CN200810023298 A CN 200810023298A CN 101250332 A CN101250332 A CN 101250332A
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- golden yellow
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- reactive
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- 239000000975 dye Substances 0.000 title claims abstract description 32
- 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 title claims abstract description 14
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title claims description 12
- 230000008878 coupling Effects 0.000 claims abstract description 11
- 238000010168 coupling process Methods 0.000 claims abstract description 11
- 238000005859 coupling reaction Methods 0.000 claims abstract description 11
- 239000012954 diazonium Substances 0.000 claims abstract description 11
- 150000001989 diazonium salts Chemical class 0.000 claims abstract description 8
- -1 sulphate ethyl sulphone aniline compound Chemical class 0.000 claims abstract description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 2
- 239000003513 alkali Substances 0.000 abstract description 6
- 238000004043 dyeing Methods 0.000 abstract description 4
- 150000003839 salts Chemical class 0.000 abstract description 4
- 230000002349 favourable effect Effects 0.000 abstract description 2
- 229920000742 Cotton Polymers 0.000 abstract 1
- 229910006069 SO3H Inorganic materials 0.000 abstract 1
- 239000000987 azo dye Substances 0.000 abstract 1
- 238000010017 direct printing Methods 0.000 abstract 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 abstract 1
- 125000000542 sulfonic acid group Chemical group 0.000 abstract 1
- 238000000034 method Methods 0.000 description 9
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
- 238000010998 test method Methods 0.000 description 6
- 239000004753 textile Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 238000010009 beating Methods 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 238000005303 weighing Methods 0.000 description 4
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 2
- 241000233855 Orchidaceae Species 0.000 description 2
- IQFVPQOLBLOTPF-HKXUKFGYSA-L congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 description 2
- 230000008034 disappearance Effects 0.000 description 2
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
- 239000000985 reactive dye Substances 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- INOIOAWTVPHTCJ-UHFFFAOYSA-N 6-acetamido-4-hydroxy-3-[[4-(2-sulfooxyethylsulfonyl)phenyl]diazenyl]naphthalene-2-sulfonic acid Chemical compound CC(=O)NC1=CC=C2C=C(C(N=NC3=CC=C(C=C3)S(=O)(=O)CCOS(O)(=O)=O)=C(O)C2=C1)S(O)(=O)=O INOIOAWTVPHTCJ-UHFFFAOYSA-N 0.000 description 1
- 241000532370 Atla Species 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- JNRGKDIQDBVGRD-UHFFFAOYSA-L disodium;2,5-dichloro-4-[4-[[5-[(4,6-dichloro-1,3,5-triazin-2-yl)amino]-2-sulfonatophenyl]diazenyl]-3-methyl-5-oxo-4h-pyrazol-1-yl]benzenesulfonate Chemical compound [Na+].[Na+].CC1=NN(C=2C(=CC(=C(Cl)C=2)S([O-])(=O)=O)Cl)C(=O)C1N=NC(C(=CC=1)S([O-])(=O)=O)=CC=1NC1=NC(Cl)=NC(Cl)=N1 JNRGKDIQDBVGRD-UHFFFAOYSA-L 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
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- Coloring (AREA)
Abstract
Reactive golden yellow RNL azo dye and a preparation process are disclosed, and the structural formula is showed as followed, wherein R1, R2= H, COCH3, SO3H, OCH3, CH3, C2H5, OC2H5 and the like. The dye is the mixture of various compounds which is prepared through coupling m-bis or m-bis compound acyl with diazonium salt of sulphate ethyl sulphone aniline compound which comprises sulfonic acid group or methyl group, methoxyl group, ethyl group and ethoxyl group. The dye is suitable to be used on the dying, direct printing and discharge of cotton fiber, and has excellent fastness, reproducibility, level-dyeing property, compatibility, alkali resistant salt stability and lifting power, which can match with active black KN-B to obtain black color with favorable jet black.
Description
Technical field
The present invention relates to a kind of reactive golden yellow RNL diazo dyes and preparation method thereof.
Background technology
The orange vinyl sulfone dyestuff GF with two different activities bases of Korea S reason standing grain company invention, its structure is as follows:
This dyestuff water-soluble relatively poor after adding alkali, solubleness reduces, and associates easily between dye molecule, and the avidity of fiber is increased, and easily causes the look flower, and pitch black degree is plentiful inadequately when colorant match like this, and salt and alkali resistance is poor, and degree of fixation is low.
The Huang 1 that occurs on the market in addition
#Be the yellow vinyl sulfone dyestuff with two identical active groups, its structure is as follows:
This dyestuff water-soluble relatively poor after adding alkali, solubleness is constant substantially, but on dye of light color behind the fiber and coloured light is dark partially, exist the degree of depth not enough.
Summary of the invention
The purpose of this invention is to provide and have stable performance, depth ratio Huang 1
#Deeply, a kind of reactive golden yellow RNL diazo dyes that salt and alkali resistance specific activity orange GF is good and preparation method thereof.
The structural formula of a kind of reactive golden yellow RNL diazo dyes of the present invention is as follows:
In the formula: (1) R
1, R
2=H, COCH
3, SO
3H, OCH
3, CH
3, C
2H
5, OC
2H
5Deng
Active group among the present invention contains the group that can be converted into vinyl, and its mixture is by being to be made by the diazonium salt coupling with the ethyl sulfonyl sulfate aniline compound that contains sulfonic group or methyl, methoxyl group, ethyl, oxyethyl group of two or two acylates.
The present invention prepares the method for diazonium salt and grinds little acid than diazonium for ice, and the coupling temperature is 5-15 ℃, PH=1.5-5.5.
A kind of reactive golden yellow RNL diazo dyes of the present invention and commercially available reactive orange GF, reactive yellow 1
#Deng comparing, have that salt and alkali resistance is good, favorable reproducibility, good level-dyeing property, compatibleness is good, lifting force is high, can dye dark color.Can dye, stamp, again can discharge, during its simultaneous test data are listed in the table below.
Performance index adopt following standard in table:
The general condition regulation that the GB/T2374-1994 dyeing is measured
The measuring method of insolubles content in the GB/T2381-1994 dyestuff
The measuring method of GB/T2383-1980 dyestuff screening fineness
The measuring method of GB/T2386-1980 dye well dyestuff intermediate moisture content
The measuring method of GB/T2388-1980 printing with reactive dye coloured light and intensity
The measuring method of the relative content of hydrolised dye and standard in the GB/T2389-1980 reactive dyestuffs
The measuring method of GB/T2390-1980 reactive dyestuffs pH value
The measuring method of GB/T2393-1980 printing with reactive dye degree of fixation
The measuring method of GB/T2392-1980 reactive dyestuffs thermostability
The mensuration of GB/T3671.1-1996 water-soluble dye solubleness and steady dissolution
The test method of GB/T3920-1997 textiles colour fastness to rubbing
The test method of GB/T3921.4-1997 textiles colour fastness to washing
The test method of GB/T3922-1995 textiles colour fastness to perspiration
GB/T4841.1-1984 1/1 dyeing standard depth colour atla
The test method of the heat-resisting pressure of GB/T6152-1997 textiles (flatiron) fastness
GB/T6678-1986 Chemicals sampling general provisions
GB/T8427-1998 textiles colour fastness to light test method (xenon arc)
The test method of the anti-chloride swimming-pool water colour fastness of GB/T8433-1998 textiles
Specific embodiments:
Embodiment one:
(1) takes by weighing that a two and two acylate adds the making beating of 200ml water between 24.9 parts of weight.
(2) take by weighing 28.1 parts of right-(beta-hydroxyethyl sulfone sulfate) aniline and add an amount of frozen water, add quantitative hydrochloric acid, add 6.9 parts of inferior sodium again 0 ℃ of making beating 2 hours, the blue look of control congo-red test paper, the little orchid of KI test paper, inferior sodium added afterreaction 1 hour.
Right-(beta-hydroxyethyl sulfone sulfate) diazonium salt of aniline and the coupling component that (3) will prepare are 0-5 ℃ in temperature, with coupling under the condition of sodium bicarbonate adjusting PH=4.5-5.5, react 3 hours to the diazonium salt disappearance, filter and obtain a kind of gold-tinted reactive golden yellow RNL diazo dyes.
Embodiment two: adopt embodiment one prescription, at 10-15 ℃, coupling under the condition of PH=5.5 obtains a kind of gold-tinted reactive golden yellow RNL diazo dyes.
Embodiment three:
(1) takes by weighing two and two acylate 200ml water making beating between 23.8 parts of weight.
(2) take by weighing 28.1 parts of right-(beta-hydroxyethyl sulfone sulfate) aniline of weight and add an amount of frozen water, add quantitative hydrochloric acid, add 6.9 parts of inferior sodium again 0 ℃ of making beating 2 hours, the blue look of control congo-red test paper, the little orchid of KI test paper, inferior sodium added afterreaction 1 hour.
Diazonium salt of right-(beta-hydroxyethyl sulfone sulfate) aniline that (3) will prepare and coupling component temperature are at 0-5 ℃, with coupling under the part of sodium bicarbonate adjusting PH=4-4.5, react 3 hours to the diazonium salt disappearance, filter and obtain a kind of gold-tinted reactive golden yellow RNL diazo dyes.
Embodiment four: take the prescription of embodiment three, at 10-15 ℃, coupling under the part of PH=5-5.5 obtains the golden yellow RNL azoic dyestuff of kind ruddiness.
Claims (6)
1. reactive golden yellow RNL diazo dyes, its structural formula is as follows:
In the formula: R
1, R
2=H, COCH
3, SO
3H, OCH
3, CH
3, C
2H
5Perhaps OC
2H
5
2. according to right 1 described a kind of reactive golden yellow RNL diazo dyes, it is characterized in that containing the ethyl sulfonyl sulfate group.
3. according to right 1 described a kind of reactive golden yellow RNL diazo dyes, it is characterized in that the ethyl sulfonyl sulfate group can be converted into the group of vinyl.
4. according to the preparation method of the described dyestuff of claim 1, be that the diazonium salt by two or two acylates and the ethyl sulfonyl sulfate aniline compound that contains sulfonic group or methyl, methoxyl group, ethyl, oxyethyl group carries out the mixture that coupling must contain multiple compound.
5. according to the preparation method of the described dyestuff of claim 4, it is characterized in that its diazonium mode compares diazonium for the little acid of ice mill.
6. according to the preparation method of the described dyestuff of claim 4, it is characterized in that its coupling temperature is 5-15 ℃, PH=1.5-5.5.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2008100232982A CN101250332A (en) | 2008-04-08 | 2008-04-08 | Reactive golden yellow RNL diazo dyes and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2008100232982A CN101250332A (en) | 2008-04-08 | 2008-04-08 | Reactive golden yellow RNL diazo dyes and preparation method thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN101250332A true CN101250332A (en) | 2008-08-27 |
Family
ID=39953942
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNA2008100232982A Pending CN101250332A (en) | 2008-04-08 | 2008-04-08 | Reactive golden yellow RNL diazo dyes and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN101250332A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103102684A (en) * | 2013-02-20 | 2013-05-15 | 合肥杰事杰新材料股份有限公司 | Weather-proof and hydrolysis-resistant continuous glass fiber reinforced polyamide composite material and its preparation method |
| CN112876875A (en) * | 2020-12-31 | 2021-06-01 | 湖北丽源科技股份有限公司 | Disazo reactive yellow dye and preparation method and application thereof |
-
2008
- 2008-04-08 CN CNA2008100232982A patent/CN101250332A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103102684A (en) * | 2013-02-20 | 2013-05-15 | 合肥杰事杰新材料股份有限公司 | Weather-proof and hydrolysis-resistant continuous glass fiber reinforced polyamide composite material and its preparation method |
| CN103102684B (en) * | 2013-02-20 | 2016-12-28 | 合肥杰事杰新材料股份有限公司 | A kind of weather-proof resistant to hydrolysis continuous glass-fiber reinforced polyamide composite and preparation method thereof |
| CN112876875A (en) * | 2020-12-31 | 2021-06-01 | 湖北丽源科技股份有限公司 | Disazo reactive yellow dye and preparation method and application thereof |
| CN112876875B (en) * | 2020-12-31 | 2022-05-20 | 湖北丽源科技股份有限公司 | Disazo reactive yellow dye and preparation method and application thereof |
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| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
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Open date: 20080827 |