DE1206108B - Verfahren zur Herstellung von wasserloeslichen gelben Monoazofarbstoffen - Google Patents
Verfahren zur Herstellung von wasserloeslichen gelben MonoazofarbstoffenInfo
- Publication number
- DE1206108B DE1206108B DEF36927A DEF0036927A DE1206108B DE 1206108 B DE1206108 B DE 1206108B DE F36927 A DEF36927 A DE F36927A DE F0036927 A DEF0036927 A DE F0036927A DE 1206108 B DE1206108 B DE 1206108B
- Authority
- DE
- Germany
- Prior art keywords
- parts
- weight
- water
- group
- methyl
- 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.)
- Pending
Links
- 239000000975 dye Substances 0.000 title claims description 25
- 238000000034 method Methods 0.000 title claims description 5
- 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 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 150000001555 benzenes Chemical class 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 3
- 229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 claims description 3
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 3
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 238000004040 coloring Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 238000004043 dyeing Methods 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 6
- 230000008878 coupling Effects 0.000 description 6
- 238000010168 coupling process Methods 0.000 description 6
- 238000005859 coupling reaction Methods 0.000 description 6
- 229920003043 Cellulose fiber Polymers 0.000 description 5
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 4
- 150000008049 diazo compounds Chemical class 0.000 description 4
- 239000001632 sodium acetate Substances 0.000 description 4
- 235000017281 sodium acetate Nutrition 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- ZRHUHDUEXWHZMA-UHFFFAOYSA-N 1,4-dihydropyrazol-5-one Chemical compound O=C1CC=NN1 ZRHUHDUEXWHZMA-UHFFFAOYSA-N 0.000 description 3
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 239000000987 azo dye Substances 0.000 description 3
- 239000001103 potassium chloride Substances 0.000 description 3
- 235000011164 potassium chloride Nutrition 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- QZFQLZZNYXSEQR-UHFFFAOYSA-N 3-chloro-4-(3-methyl-5-oxo-4h-pyrazol-1-yl)benzenesulfonic acid Chemical compound O=C1CC(C)=NN1C1=CC=C(S(O)(=O)=O)C=C1Cl QZFQLZZNYXSEQR-UHFFFAOYSA-N 0.000 description 2
- CWJQQASJVVAXKL-UHFFFAOYSA-N 4-(3-Methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl)benzenesulfonic acid Chemical compound O=C1CC(C)=NN1C1=CC=C(S(O)(=O)=O)C=C1 CWJQQASJVVAXKL-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- LUZXGSRCYGQGQF-UHFFFAOYSA-N 2,5-dichloro-4-(5-methyl-3-oxo-1h-pyrazol-2-yl)benzenesulfonic acid Chemical compound N1C(C)=CC(=O)N1C1=CC(Cl)=C(S(O)(=O)=O)C=C1Cl LUZXGSRCYGQGQF-UHFFFAOYSA-N 0.000 description 1
- FHOSUHKLSWNJJZ-UHFFFAOYSA-N 2-(3-methyl-5-oxo-4h-pyrazol-1-yl)benzenesulfonic acid Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1S(O)(=O)=O FHOSUHKLSWNJJZ-UHFFFAOYSA-N 0.000 description 1
- TWCZFZWZLLVQRA-UHFFFAOYSA-N 2-[(4-aminobenzoyl)amino]benzoic acid Chemical compound C1=CC(N)=CC=C1C(=O)NC1=CC=CC=C1C(O)=O TWCZFZWZLLVQRA-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical class ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- -1 sulfuric acid ester Chemical class 0.000 description 1
- 239000001043 yellow dye Substances 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
- C09B62/503—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring the reactive group being an esterified or non-esterified hydroxyalkyl sulfonyl or mercaptoalkyl sulfonyl group, a quaternised or non-quaternised aminoalkyl sulfonyl group, a heterylmercapto alkyl sulfonyl group, a vinyl sulfonyl or a substituted vinyl sulfonyl group, or a thiophene-dioxide group
- C09B62/507—Azo dyes
- C09B62/51—Monoazo dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Paper (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE632985D BE632985A (en, 2012) | 1962-05-29 | ||
| BE632986D BE632986A (en, 2012) | 1962-05-29 | ||
| DEF36927A DE1206108B (de) | 1962-05-29 | 1962-05-29 | Verfahren zur Herstellung von wasserloeslichen gelben Monoazofarbstoffen |
| CH658563A CH429992A (de) | 1962-05-29 | 1963-05-27 | Verfahren zur Herstellung von wasserlöslichen gelben Monoazofarbstoffen |
| GB2133563A GB1028410A (en) | 1962-05-29 | 1963-05-28 | Water-soluble yellow monoazo-dyestuffs and process for their manufacture |
| FR936341A FR1358134A (fr) | 1962-05-29 | 1963-05-29 | Colorants monoazoïques solubles dans l'eau et leur préparation |
| FR936340A FR1358133A (fr) | 1962-05-29 | 1963-05-29 | Colorants monoazoïques jaunes solubles dans l'eau et leur préparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF36927A DE1206108B (de) | 1962-05-29 | 1962-05-29 | Verfahren zur Herstellung von wasserloeslichen gelben Monoazofarbstoffen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1206108B true DE1206108B (de) | 1965-12-02 |
Family
ID=7096671
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF36927A Pending DE1206108B (de) | 1962-05-29 | 1962-05-29 | Verfahren zur Herstellung von wasserloeslichen gelben Monoazofarbstoffen |
Country Status (4)
| Country | Link |
|---|---|
| BE (2) | BE632985A (en, 2012) |
| CH (1) | CH429992A (en, 2012) |
| DE (1) | DE1206108B (en, 2012) |
| GB (1) | GB1028410A (en, 2012) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117402506B (zh) * | 2023-10-18 | 2024-06-18 | 江苏德美科化工有限公司 | 一种黄色活性染料及其制备方法 |
-
0
- BE BE632986D patent/BE632986A/xx unknown
- BE BE632985D patent/BE632985A/xx unknown
-
1962
- 1962-05-29 DE DEF36927A patent/DE1206108B/de active Pending
-
1963
- 1963-05-27 CH CH658563A patent/CH429992A/de unknown
- 1963-05-28 GB GB2133563A patent/GB1028410A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BE632986A (en, 2012) | |
| BE632985A (en, 2012) | |
| GB1028410A (en) | 1966-05-04 |
| CH429992A (de) | 1967-02-15 |
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