DE1276844B - Verfahren zur Herstellung von wasserloeslichen Azofarbstoffen - Google Patents
Verfahren zur Herstellung von wasserloeslichen AzofarbstoffenInfo
- Publication number
- DE1276844B DE1276844B DEF44381A DEF0044381A DE1276844B DE 1276844 B DE1276844 B DE 1276844B DE F44381 A DEF44381 A DE F44381A DE F0044381 A DEF0044381 A DE F0044381A DE 1276844 B DE1276844 B DE 1276844B
- Authority
- DE
- Germany
- Prior art keywords
- parts
- formula
- water
- volume
- dye
- 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
- 238000000034 method Methods 0.000 title claims description 13
- 239000000987 azo dye Substances 0.000 title claims description 12
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 239000000975 dye Substances 0.000 claims description 54
- 150000003839 salts Chemical class 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 14
- DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical class OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 claims description 12
- 230000008878 coupling Effects 0.000 claims description 10
- 238000010168 coupling process Methods 0.000 claims description 10
- 238000005859 coupling reaction Methods 0.000 claims description 10
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 150000001340 alkali metals Chemical group 0.000 claims description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 238000004040 coloring Methods 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 41
- 239000000243 solution Substances 0.000 description 33
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 23
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 20
- 229920000742 Cotton Polymers 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 239000011734 sodium Substances 0.000 description 17
- 238000002425 crystallisation Methods 0.000 description 12
- 230000008025 crystallization Effects 0.000 description 12
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 12
- 235000019345 sodium thiosulphate Nutrition 0.000 description 12
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 11
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- -1 heterocyclic enols Chemical class 0.000 description 10
- 229910000029 sodium carbonate Inorganic materials 0.000 description 10
- 239000011780 sodium chloride Substances 0.000 description 10
- 239000007795 chemical reaction product Substances 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 7
- 238000004043 dyeing Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 210000002268 wool Anatomy 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 6
- 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 5
- 239000002253 acid Substances 0.000 description 5
- 239000003513 alkali Substances 0.000 description 5
- 239000001103 potassium chloride Substances 0.000 description 5
- 235000011164 potassium chloride Nutrition 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 235000010288 sodium nitrite Nutrition 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000012954 diazonium Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- NZDXSXLYLMHYJA-UHFFFAOYSA-M 4-[(1,3-dimethylimidazol-1-ium-2-yl)diazenyl]-n,n-dimethylaniline;chloride Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1N=NC1=[N+](C)C=CN1C NZDXSXLYLMHYJA-UHFFFAOYSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000004952 Polyamide Substances 0.000 description 3
- 206010039587 Scarlet Fever Diseases 0.000 description 3
- POJOORKDYOPQLS-UHFFFAOYSA-L barium(2+) 5-chloro-2-[(2-hydroxynaphthalen-1-yl)diazenyl]-4-methylbenzenesulfonate Chemical compound [Ba+2].C1=C(Cl)C(C)=CC(N=NC=2C3=CC=CC=C3C=CC=2O)=C1S([O-])(=O)=O.C1=C(Cl)C(C)=CC(N=NC=2C3=CC=CC=C3C=CC=2O)=C1S([O-])(=O)=O POJOORKDYOPQLS-UHFFFAOYSA-L 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000006193 diazotization reaction Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229920002647 polyamide Polymers 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000005185 salting out Methods 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-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
- 239000002152 aqueous-organic solution Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 2
- 239000002657 fibrous material Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- LCAGAKXGPVINGX-UHFFFAOYSA-N n-(4-aminophenyl)-2-chloroacetamide Chemical compound NC1=CC=C(NC(=O)CCl)C=C1 LCAGAKXGPVINGX-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical class C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical class C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 1
- LDAZSVRDAYKFDR-UHFFFAOYSA-N 2-amino-5-[(2-chloroacetyl)amino]benzenesulfonic acid Chemical compound NC1=CC=C(NC(=O)CCl)C=C1S(O)(=O)=O LDAZSVRDAYKFDR-UHFFFAOYSA-N 0.000 description 1
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 1
- PUPDISBRKNJGKV-UHFFFAOYSA-N 4-[(2-chloroacetyl)amino]-5-hydroxynaphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(NC(=O)CCl)=C2C(O)=CC(S(O)(=O)=O)=CC2=C1 PUPDISBRKNJGKV-UHFFFAOYSA-N 0.000 description 1
- UJYBNBHDROTBGS-UHFFFAOYSA-N 4-amino-2-[(2-chloroacetyl)amino]benzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C(NC(=O)CCl)=C1 UJYBNBHDROTBGS-UHFFFAOYSA-N 0.000 description 1
- XIQKALDENTUXBY-UHFFFAOYSA-N 4-hydroxynaphthalene-1,5-disulfonic acid Chemical compound C1=CC(S(O)(=O)=O)=C2C(O)=CC=C(S(O)(=O)=O)C2=C1 XIQKALDENTUXBY-UHFFFAOYSA-N 0.000 description 1
- GEUSVGFAUFRAQI-UHFFFAOYSA-N 6-[(2-chloroacetyl)amino]-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(NC(=O)CCl)C=C2C(O)=CC(S(O)(=O)=O)=CC2=C1 GEUSVGFAUFRAQI-UHFFFAOYSA-N 0.000 description 1
- CWBJFAHPCUSERS-UHFFFAOYSA-N 7-[(2-chloroacetyl)amino]-4-hydroxynaphthalene-2-sulfonic acid Chemical compound ClCC(=O)NC1=CC=C2C(O)=CC(S(O)(=O)=O)=CC2=C1 CWBJFAHPCUSERS-UHFFFAOYSA-N 0.000 description 1
- PZFFLVKPHQPAQM-UHFFFAOYSA-N COC(C=C(C(OC)=C1)NC(CCl)=O)=C1N Chemical compound COC(C=C(C(OC)=C1)NC(CCl)=O)=C1N PZFFLVKPHQPAQM-UHFFFAOYSA-N 0.000 description 1
- 229920003043 Cellulose fiber Polymers 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical class OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- MYDCNTHXHBFWGI-UHFFFAOYSA-N N-(5-amino-2-methoxyphenyl)-2-chloroacetamide Chemical compound COC1=CC=C(N)C=C1NC(=O)CCl MYDCNTHXHBFWGI-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000004133 Sodium thiosulphate Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical class CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 150000002081 enamines Chemical class 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 229940083761 high-ceiling diuretics pyrazolone derivative Drugs 0.000 description 1
- 150000005204 hydroxybenzenes Chemical class 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- CWWSUADYATWNKB-UHFFFAOYSA-N n-(3-aminophenyl)-3-chloropropanamide Chemical compound NC1=CC=CC(NC(=O)CCCl)=C1 CWWSUADYATWNKB-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- MGQNMYSRDBFUIR-UHFFFAOYSA-N nitro cyanoformate Chemical compound [O-][N+](=O)OC(=O)C#N MGQNMYSRDBFUIR-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 229920006306 polyurethane fiber Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 239000004552 water soluble powder 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
- C09B62/465—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 acryloyl group, a quaternised or non-quaternised aminoalkyl carbonyl group or a (—N)n—CO—A—O—X or (—N)n—CO—A—Hal group, wherein A is an alkylene or alkylidene group, X is hydrogen or an acyl radical of an organic or inorganic acid, Hal is a halogen atom, and n is 0 or 1
- C09B62/47—Azo dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF44381A DE1276844B (de) | 1964-11-06 | 1964-11-06 | Verfahren zur Herstellung von wasserloeslichen Azofarbstoffen |
| US505233A US3435023A (en) | 1964-11-06 | 1965-10-26 | Water-soluble mono and disazo dyestuffs containing n-(thiosulfato-alkanoylamino) groups |
| CH1520765A CH459408A (de) | 1964-11-06 | 1965-11-04 | Verfahren zur Herstellung von wasserlöslichen Mono- oder Disazofarbstoffen |
| AT997565A AT260392B (de) | 1964-11-06 | 1965-11-04 | Verfahren zur Herstellung von neuen, wasserlöslichen Mono- und Disazofarbstoffen |
| CH633668A CH478900A (de) | 1964-11-06 | 1965-11-04 | Verfahren zur Herstellung von wasserlöslichen Mono- oder Disazofarbstoffen |
| FR37543A FR1455505A (fr) | 1964-11-06 | 1965-11-06 | Colorants mono- et disazoïques et leur préparation |
| GB47249/65A GB1117747A (en) | 1964-11-06 | 1965-11-08 | Water-soluble mono and disazo dyestuffs and processes for their manufacture |
| BE672011D BE672011A (enExample) | 1964-11-06 | 1965-11-08 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF44381A DE1276844B (de) | 1964-11-06 | 1964-11-06 | Verfahren zur Herstellung von wasserloeslichen Azofarbstoffen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1276844B true DE1276844B (de) | 1968-09-05 |
Family
ID=7100016
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF44381A Pending DE1276844B (de) | 1964-11-06 | 1964-11-06 | Verfahren zur Herstellung von wasserloeslichen Azofarbstoffen |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3435023A (enExample) |
| AT (1) | AT260392B (enExample) |
| BE (1) | BE672011A (enExample) |
| CH (1) | CH459408A (enExample) |
| DE (1) | DE1276844B (enExample) |
| FR (1) | FR1455505A (enExample) |
| GB (1) | GB1117747A (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1922940A1 (de) * | 1969-05-06 | 1970-11-26 | Cassella Farbwerke Mainkur Ag | Azofarbstoffe der Pyrazolonreihe |
| US4036825A (en) * | 1971-11-05 | 1977-07-19 | Hoechst Aktiengesellschaft | Monoazo reactive dyestuffs |
| US3889271A (en) * | 1972-12-01 | 1975-06-10 | Agfa Gevaert Ag | Ink jet process utilizing novel dyes |
| DE2817033C2 (de) * | 1978-04-19 | 1983-03-24 | Basf Ag, 6700 Ludwigshafen | Reaktivfarbstoffe |
| DE3940266A1 (de) * | 1989-12-06 | 1991-06-13 | Bayer Ag | Azofarbstoffe und deren verwendung |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1254830A (fr) * | 1960-04-25 | 1961-02-24 | Hoechst Ag | Colorants azoïques solubles dans l'eau contenant un ou plusieurs groupes thiosulfuriques et leur préparation |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA677934A (en) * | 1964-01-14 | Farbwerke Hoechst Aktiengesellschaft Vormals Meister Lucius And Bruning | Water-soluble azo-dyestuffs containing one or more thiosulfuric acid groups | |
| DE1163473B (de) * | 1959-04-24 | 1964-02-20 | Hoechst Ag | Verfahren zur Herstellung von eine oder mehrere Thioschwefelsaeuregruppen enthaltenden wasserloeslichen Phthalocyaninfarbstoffen |
| AT221511B (de) * | 1960-07-08 | 1962-06-12 | Basf Ag | Verfahren zur Herstellung von N-substituierten β-Hydroxypropionsäureamid-Derivaten |
| CH385787A (de) * | 1960-10-04 | 1964-09-15 | Hoechst Ag | Verfahren zur Herstellung von nassechten Färbungen auf Cellulosetextilmaterialien |
-
1964
- 1964-11-06 DE DEF44381A patent/DE1276844B/de active Pending
-
1965
- 1965-10-26 US US505233A patent/US3435023A/en not_active Expired - Lifetime
- 1965-11-04 AT AT997565A patent/AT260392B/de active
- 1965-11-04 CH CH1520765A patent/CH459408A/de unknown
- 1965-11-06 FR FR37543A patent/FR1455505A/fr not_active Expired
- 1965-11-08 BE BE672011D patent/BE672011A/xx unknown
- 1965-11-08 GB GB47249/65A patent/GB1117747A/en not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1254830A (fr) * | 1960-04-25 | 1961-02-24 | Hoechst Ag | Colorants azoïques solubles dans l'eau contenant un ou plusieurs groupes thiosulfuriques et leur préparation |
Also Published As
| Publication number | Publication date |
|---|---|
| AT260392B (de) | 1968-03-11 |
| CH459408A (de) | 1968-07-15 |
| GB1117747A (en) | 1968-06-26 |
| FR1455505A (fr) | 1966-04-01 |
| US3435023A (en) | 1969-03-25 |
| BE672011A (enExample) | 1966-05-09 |
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