CH410239A - Verfahren zur Herstellung neuer Azofarbstoffe - Google Patents
Verfahren zur Herstellung neuer AzofarbstoffeInfo
- Publication number
- CH410239A CH410239A CH7585659A CH7585659A CH410239A CH 410239 A CH410239 A CH 410239A CH 7585659 A CH7585659 A CH 7585659A CH 7585659 A CH7585659 A CH 7585659A CH 410239 A CH410239 A CH 410239A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- acid
- sulfonic acid
- aminobenzene
- amino
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 12
- 239000000987 azo dye Substances 0.000 title claims description 3
- 239000000975 dye Substances 0.000 claims description 19
- ZMCHBSMFKQYNKA-UHFFFAOYSA-N 2-aminobenzenesulfonic acid Chemical class NC1=CC=CC=C1S(O)(=O)=O ZMCHBSMFKQYNKA-UHFFFAOYSA-N 0.000 claims description 5
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 229910006069 SO3H Inorganic materials 0.000 claims 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 1
- 239000002253 acid Substances 0.000 description 22
- 230000008878 coupling Effects 0.000 description 7
- 238000010168 coupling process Methods 0.000 description 7
- 238000005859 coupling reaction Methods 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000004043 dyeing Methods 0.000 description 6
- 239000007859 condensation product Substances 0.000 description 5
- 150000008049 diazo compounds Chemical class 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 229920000742 Cotton Polymers 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 3
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 3
- -1 amino monoazo Chemical group 0.000 description 3
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 3
- UWPJYQYRSWYIGZ-UHFFFAOYSA-N 5-aminonaphthalene-2-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=C2C(N)=CC=CC2=C1 UWPJYQYRSWYIGZ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000006193 diazotization reaction Methods 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- CFCXQQUQLZIZPI-UHFFFAOYSA-N 2-amino-3,5-dimethylbenzenesulfonic acid Chemical compound CC1=CC(C)=C(N)C(S(O)(=O)=O)=C1 CFCXQQUQLZIZPI-UHFFFAOYSA-N 0.000 description 1
- VJHJWHAIOWSVCP-UHFFFAOYSA-N 2-amino-5-chloro-3-methylbenzenesulfonic acid Chemical compound CC1=CC(Cl)=CC(S(O)(=O)=O)=C1N VJHJWHAIOWSVCP-UHFFFAOYSA-N 0.000 description 1
- KZKGEEGADAWJFS-UHFFFAOYSA-N 2-amino-5-methoxybenzenesulfonic acid Chemical compound COC1=CC=C(N)C(S(O)(=O)=O)=C1 KZKGEEGADAWJFS-UHFFFAOYSA-N 0.000 description 1
- LDCCBULMAFILCT-UHFFFAOYSA-N 2-aminobenzene-1,4-disulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=CC=C1S(O)(=O)=O LDCCBULMAFILCT-UHFFFAOYSA-N 0.000 description 1
- QPKNFEVLZVJGBM-UHFFFAOYSA-N 2-aminonaphthalen-1-ol Chemical compound C1=CC=CC2=C(O)C(N)=CC=C21 QPKNFEVLZVJGBM-UHFFFAOYSA-N 0.000 description 1
- GWIAAIUASRVOIA-UHFFFAOYSA-N 2-aminonaphthalene-1-sulfonic acid Chemical class C1=CC=CC2=C(S(O)(=O)=O)C(N)=CC=C21 GWIAAIUASRVOIA-UHFFFAOYSA-N 0.000 description 1
- BWQHQLOGZIBRON-UHFFFAOYSA-N 3-(aminodiazenyl)naphthalene-1,2-disulfonic acid Chemical compound NN=NC1=C(C(=C2C=CC=CC2=C1)S(=O)(=O)O)S(=O)(=O)O BWQHQLOGZIBRON-UHFFFAOYSA-N 0.000 description 1
- UGTPGYYOFCLPJH-UHFFFAOYSA-N 3-acetamido-2-aminobenzenesulfonic acid Chemical compound CC(=O)NC1=CC=CC(S(O)(=O)=O)=C1N UGTPGYYOFCLPJH-UHFFFAOYSA-N 0.000 description 1
- FLIOATBXVNLPLK-UHFFFAOYSA-N 3-amino-4-methoxybenzenesulfonic acid Chemical compound COC1=CC=C(S(O)(=O)=O)C=C1N FLIOATBXVNLPLK-UHFFFAOYSA-N 0.000 description 1
- XRTJYEIMLZALBD-UHFFFAOYSA-N 4-(6-methyl-1,3-benzothiazol-2-yl)aniline Chemical compound S1C2=CC(C)=CC=C2N=C1C1=CC=C(N)C=C1 XRTJYEIMLZALBD-UHFFFAOYSA-N 0.000 description 1
- WQTCZINVPXJNEL-UHFFFAOYSA-N 4-amino-3-methylbenzenesulfonic acid Chemical compound CC1=CC(S(O)(=O)=O)=CC=C1N WQTCZINVPXJNEL-UHFFFAOYSA-N 0.000 description 1
- NDYYJXGERWTRSD-UHFFFAOYSA-N 4-aminonaphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=C2C(N)=CC(S(O)(=O)=O)=CC2=C1 NDYYJXGERWTRSD-UHFFFAOYSA-N 0.000 description 1
- PHRVJZNHPVJYOM-UHFFFAOYSA-N 5-acetamido-2-aminobenzenesulfonic acid Chemical compound CC(=O)NC1=CC=C(N)C(S(O)(=O)=O)=C1 PHRVJZNHPVJYOM-UHFFFAOYSA-N 0.000 description 1
- GHBWBMDGBCKAQU-OWOJBTEDSA-N 5-amino-2-[(e)-2-(4-nitro-2-sulfophenyl)ethenyl]benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC(N)=CC=C1\C=C\C1=CC=C([N+]([O-])=O)C=C1S(O)(=O)=O GHBWBMDGBCKAQU-OWOJBTEDSA-N 0.000 description 1
- FSXVZWAWYKMFMX-UHFFFAOYSA-N 5-amino-2-methylbenzoic acid Chemical compound CC1=CC=C(N)C=C1C(O)=O FSXVZWAWYKMFMX-UHFFFAOYSA-N 0.000 description 1
- OXQJOAGKNHVOAI-UHFFFAOYSA-N 5-amino-6-methoxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=CC2=C(N)C(OC)=CC=C21 OXQJOAGKNHVOAI-UHFFFAOYSA-N 0.000 description 1
- RMMXTBMQSGEXHJ-UHFFFAOYSA-N Aminophenazone Chemical compound O=C1C(N(C)C)=C(C)N(C)N1C1=CC=CC=C1 RMMXTBMQSGEXHJ-UHFFFAOYSA-N 0.000 description 1
- 229920003043 Cellulose fiber Polymers 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 230000002238 attenuated effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000009967 direct dyeing Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000009980 pad dyeing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- RCTGMCJBQGBLKT-PAMTUDGESA-N scarlet red Chemical compound CC1=CC=CC=C1\N=N\C(C=C1C)=CC=C1\N=N\C1=C(O)C=CC2=CC=CC=C12 RCTGMCJBQGBLKT-PAMTUDGESA-N 0.000 description 1
- 229960005369 scarlet red Drugs 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 210000002268 wool Anatomy 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
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/04—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring
- C09B62/08—Azo dyes
- C09B62/09—Disazo or polyazo dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Priority Applications (16)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL242192D NL242192A (en。) | 1958-08-11 | ||
| CH7583059A CH402226A (de) | 1958-08-11 | 1959-07-16 | Verfahren zur Herstellung neuer Azophthalocyaninfarbstoffe |
| CH7585659A CH410239A (de) | 1959-07-17 | 1959-07-17 | Verfahren zur Herstellung neuer Azofarbstoffe |
| CH1148560A CH413163A (de) | 1958-08-11 | 1959-07-17 | Verfahren zur Herstellung neuer Azofarbstoffe |
| GB2698859A GB903408A (en) | 1958-08-11 | 1959-08-06 | New disazo-dyestuffs containing halogenotriazine residues and their manufacture and use |
| DEC19578A DE1138176B (de) | 1958-08-11 | 1959-08-08 | Verfahren zur Herstellung von Azofarbstoffen |
| NL242192A NL121182C (en。) | 1959-07-17 | 1959-08-10 | |
| ES0251608A ES251608A1 (es) | 1958-08-11 | 1959-08-10 | Procedimiento para la preparacion de nuevos colorantes azoicos |
| BE582028A BE582028A (fr) | 1958-08-27 | 1959-08-26 | Nouveaux composés complexes métallifères de colorants monoazoïques, leur procédé d'obtention et leur utilisation |
| CH118360A CH422196A (de) | 1958-08-11 | 1960-02-03 | Verfahren zur Herstellung neuer Azofarbstoffe |
| GB1055760A GB931187A (en) | 1958-08-11 | 1960-03-24 | New azo-anthraquinone-dyestuffs containing chloro-triazine residues and their manufacture and use |
| GB2433060A GB949502A (en) | 1958-08-11 | 1960-07-12 | New azophthalocyanine dyestuffs and their manufacture and use |
| DEC21925A DE1192346B (de) | 1958-08-11 | 1960-07-15 | Verfahren zur Herstellung von Azophthalocyaninfarbstoffen |
| DEC21934A DE1211733B (de) | 1958-08-11 | 1960-07-16 | Verfahren zur Herstellung von Azofarbstoffen |
| ES0259724A ES259724A2 (es) | 1959-07-17 | 1960-07-16 | Procedimiento para la preparaciën de nuevos colorantes azoicos |
| US124361A US3100768A (en) | 1958-08-11 | 1961-07-17 | Azo dyestuffs |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH7585659A CH410239A (de) | 1959-07-17 | 1959-07-17 | Verfahren zur Herstellung neuer Azofarbstoffe |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH410239A true CH410239A (de) | 1966-03-31 |
Family
ID=4534494
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH7585659A CH410239A (de) | 1958-08-11 | 1959-07-17 | Verfahren zur Herstellung neuer Azofarbstoffe |
Country Status (2)
| Country | Link |
|---|---|
| CH (1) | CH410239A (en。) |
| NL (1) | NL121182C (en。) |
-
1959
- 1959-07-17 CH CH7585659A patent/CH410239A/de unknown
- 1959-08-10 NL NL242192A patent/NL121182C/xx active
Also Published As
| Publication number | Publication date |
|---|---|
| NL121182C (en。) | 1966-08-16 |
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