DE1644213C3 - Wasserlösliche Disazoreaktivfarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zum Färben oder Bedrucken von Zellulosematerialien und stickstoffhaltigen Materialiea - Google Patents
Wasserlösliche Disazoreaktivfarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zum Färben oder Bedrucken von Zellulosematerialien und stickstoffhaltigen MaterialieaInfo
- Publication number
- DE1644213C3 DE1644213C3 DE1644213A DE1644213A DE1644213C3 DE 1644213 C3 DE1644213 C3 DE 1644213C3 DE 1644213 A DE1644213 A DE 1644213A DE 1644213 A DE1644213 A DE 1644213A DE 1644213 C3 DE1644213 C3 DE 1644213C3
- Authority
- DE
- Germany
- Prior art keywords
- aminonaphthalene
- parts
- acid
- amino
- sulfonic acid
- 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
Links
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title claims description 15
- 238000004043 dyeing Methods 0.000 title description 9
- 239000000463 material Substances 0.000 title description 7
- 238000000034 method Methods 0.000 title description 5
- 238000002360 preparation method Methods 0.000 title description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 title description 3
- 239000000985 reactive dye Substances 0.000 title description 3
- 239000002253 acid Substances 0.000 claims description 34
- 239000000975 dye Substances 0.000 claims description 30
- 150000007513 acids Chemical class 0.000 claims description 4
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Inorganic materials [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 15
- 239000000203 mixture Substances 0.000 description 13
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 9
- 230000008878 coupling Effects 0.000 description 9
- 238000010168 coupling process Methods 0.000 description 9
- 238000005859 coupling reaction Methods 0.000 description 9
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
- 239000011780 sodium chloride Substances 0.000 description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 229920000742 Cotton Polymers 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- 239000001103 potassium chloride Substances 0.000 description 5
- 235000011164 potassium chloride Nutrition 0.000 description 5
- VOWZNBNDMFLQGM-UHFFFAOYSA-N 2,5-dimethylaniline Chemical compound CC1=CC=C(C)C(N)=C1 VOWZNBNDMFLQGM-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical class ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 4
- BUKHSQBUKZIMLB-UHFFFAOYSA-L potassium;sodium;dichloride Chemical compound [Na+].[Cl-].[Cl-].[K+] BUKHSQBUKZIMLB-UHFFFAOYSA-L 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 3
- 239000012736 aqueous medium Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- AUCCSYASSQDNOJ-UHFFFAOYSA-N 1-amino-2h-naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(N)(S(O)(=O)=O)CC=CC2=C1 AUCCSYASSQDNOJ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 2
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
- 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
- 229920003043 Cellulose fiber Polymers 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- -1 aminomonoazo Chemical group 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 150000008049 diazo compounds Chemical class 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 150000002790 naphthalenes Chemical class 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000004627 regenerated cellulose Substances 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- DNPFVNDXMLQWQB-UHFFFAOYSA-N 3-(2,2,3,3-tetrafluorocyclobutyl)prop-2-enoyl chloride Chemical compound FC1(F)CC(C=CC(Cl)=O)C1(F)F DNPFVNDXMLQWQB-UHFFFAOYSA-N 0.000 description 1
- MTJGVAJYTOXFJH-UHFFFAOYSA-N 3-aminonaphthalene-1,5-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 MTJGVAJYTOXFJH-UHFFFAOYSA-N 0.000 description 1
- GNQNCWDIVKLSAJ-UHFFFAOYSA-N 4-aminobenzene-1,2,3-trisulfonic acid Chemical class NC1=CC=C(S(O)(=O)=O)C(S(O)(=O)=O)=C1S(O)(=O)=O GNQNCWDIVKLSAJ-UHFFFAOYSA-N 0.000 description 1
- IMUUNYPYNWXUBO-UHFFFAOYSA-N 4-aminobenzene-1,3-disulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1S(O)(=O)=O IMUUNYPYNWXUBO-UHFFFAOYSA-N 0.000 description 1
- SWHYBBGFRAEKOS-UHFFFAOYSA-N 4-aminonaphthalene-1,3,6-trisulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C(N)=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=C1 SWHYBBGFRAEKOS-UHFFFAOYSA-N 0.000 description 1
- NBMNUPZHNCDTIM-UHFFFAOYSA-N 5-aminonaphthalene-1,3,7-trisulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C(N)=CC(S(O)(=O)=O)=CC2=C1S(O)(=O)=O NBMNUPZHNCDTIM-UHFFFAOYSA-N 0.000 description 1
- QEZZCWMQXHXAFG-UHFFFAOYSA-N 8-aminonaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C(N)=CC=CC2=C1 QEZZCWMQXHXAFG-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical group NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- 101000623895 Bos taurus Mucin-15 Proteins 0.000 description 1
- 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 1
- JKDBHOCXOBHEHB-UHFFFAOYSA-N NC1=CC=CC=C1.C1=CC=C2C(N)=CC=CC2=C1 Chemical compound NC1=CC=CC=C1.C1=CC=C2C(N)=CC=CC2=C1 JKDBHOCXOBHEHB-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 239000001049 brown dye Substances 0.000 description 1
- 125000005521 carbonamide group Chemical group 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- PEMGGJDINLGTON-UHFFFAOYSA-N n-(3-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=CC(N)=C1 PEMGGJDINLGTON-UHFFFAOYSA-N 0.000 description 1
- WXWCDTXEKCVRRO-UHFFFAOYSA-N para-Cresidine Chemical compound COC1=CC=C(C)C=C1N WXWCDTXEKCVRRO-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 238000011282 treatment Methods 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
- C09B62/44—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
- C09B62/485—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 a halo-cyclobutyl-carbonyl, halo-cyclobutyl-vinyl-carbonyl, or halo-cyclobutenyl-carbonyl group
- C09B62/489—Azo dyes
- C09B62/493—Disazo or polyazo dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0052458 | 1967-05-19 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1644213A1 DE1644213A1 (de) | 1970-07-09 |
| DE1644213B2 DE1644213B2 (de) | 1974-02-07 |
| DE1644213C3 true DE1644213C3 (de) | 1974-09-12 |
Family
ID=7105467
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1644213A Expired DE1644213C3 (de) | 1967-05-19 | 1967-05-19 | Wasserlösliche Disazoreaktivfarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zum Färben oder Bedrucken von Zellulosematerialien und stickstoffhaltigen Materialiea |
Country Status (6)
| Country | Link |
|---|---|
| AT (1) | AT274174B (cg-RX-API-DMAC10.html) |
| BE (1) | BE715421A (cg-RX-API-DMAC10.html) |
| CH (1) | CH496784A (cg-RX-API-DMAC10.html) |
| DE (1) | DE1644213C3 (cg-RX-API-DMAC10.html) |
| FR (1) | FR1567473A (cg-RX-API-DMAC10.html) |
| GB (1) | GB1188473A (cg-RX-API-DMAC10.html) |
-
1967
- 1967-05-19 DE DE1644213A patent/DE1644213C3/de not_active Expired
-
1968
- 1968-05-15 GB GB23112/68A patent/GB1188473A/en not_active Expired
- 1968-05-16 CH CH724468A patent/CH496784A/de not_active IP Right Cessation
- 1968-05-17 AT AT475768A patent/AT274174B/de active
- 1968-05-20 FR FR1567473D patent/FR1567473A/fr not_active Expired
- 1968-05-20 BE BE715421D patent/BE715421A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1188473A (en) | 1970-04-15 |
| DE1644213A1 (de) | 1970-07-09 |
| FR1567473A (cg-RX-API-DMAC10.html) | 1969-05-16 |
| AT274174B (de) | 1969-09-10 |
| BE715421A (cg-RX-API-DMAC10.html) | 1968-11-20 |
| CH496784A (de) | 1970-09-30 |
| DE1644213B2 (de) | 1974-02-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2556640C2 (de) | Reaktivfarbstoffe, deren Herstellung und Verwendung | |
| DE2927102A1 (de) | Reaktivfarbstoffe, deren herstellung und verwendung | |
| DE1644203C3 (cg-RX-API-DMAC10.html) | ||
| DE1252824B (de) | Verfahren zur Herstellung von reaktiven Farbstoffen | |
| DE1150770B (de) | Verfahren zur Herstellung von reaktiven Farbstoffen | |
| DE1210105B (de) | Verfahren zur Herstellung metallhaltiger Reaktivfarbstoffe | |
| DE1223971B (de) | Verfahren zur Herstellung kupferhaltiger, faserreaktiver Monoazofarbstoffe | |
| DE2838540A1 (de) | Farbstoffe, deren herstellung und verwendung | |
| CH467838A (de) | Verfahren zur Herstellung metallfreier Azofarbstoffe | |
| DE3045789A1 (de) | Faseraktive azofarbstoffe, verfahren zu ihrer herstellung und ihre verwendung zum faerben und bedrucken von hydroxylgruppen- und/oder stickstoffhaltigen fasermaterialien | |
| DE1644213C3 (de) | Wasserlösliche Disazoreaktivfarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zum Färben oder Bedrucken von Zellulosematerialien und stickstoffhaltigen Materialiea | |
| DE2414871A1 (de) | Neue reaktivfarbstoffe | |
| DE1225319B (de) | Verfahren zur Herstellung von Azofarbstoffen | |
| DE1960895C3 (de) | Wasserlösliche, reaktive Monoazofarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zum Färben oder Bedrucken von Leder oder Fasermaterialien aus Wolle, Seide, Polyamiden, Polyurethanen, regenerierten Proteinfasern oder nativen oder regenerierten Cellulosefasern | |
| DE69903090T2 (de) | Wasserlösliche halogentriazinhaltige Azoverbindungen, Verfahren zu deren Herstellung und ihre Verwendung als Farbstoffe | |
| DE1544541C3 (cg-RX-API-DMAC10.html) | ||
| DE1544500B2 (de) | Metallhaltige disazoreaktivfarbstoffe und verfahren zu deren herstellung | |
| DE1644198C3 (de) | Metallfreie, wasserlösliche Disazofarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung | |
| DE2047025C3 (de) | Wasserlösliche 1 zu 1-Kupferkomplex-Disazofarbstoffe, Verfahren zu deren Herstellung und ihre Verwendung zum Färben oder Bedrucken von nativen oder regenerierten Cellulosefaser«, Leder, Wolle, Seide, Polyamid- oder Polyurethanfasern | |
| DE2324847C3 (de) | Wasserlösliche, reaktive Monoazofarbstoffe, sowie Verfahren zu deren Herstellung und Verwendung zum Färben oder Bedrucken von Fasermaterial | |
| DE1211733B (de) | Verfahren zur Herstellung von Azofarbstoffen | |
| DE1231365B (de) | Verfahren zur Herstellung faserreaktiver Azofarbstoffe | |
| DE1544570C (de) | Verfahren zur Herstellung reaktiver Farbstoffe | |
| DE1769175B2 (de) | Wasserlösliche Polyazofarbstoffe, Verfahren zu ihrer Herstellung und deren Verwendung | |
| DE1544505C3 (de) | Reaktivfarbstoffe und Verfahren zu deren Herstellung und Anwendung |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |