DE2239814C2 - Monoazofarbstoffe und ihre Verwendung - Google Patents
Monoazofarbstoffe und ihre VerwendungInfo
- Publication number
- DE2239814C2 DE2239814C2 DE2239814A DE2239814A DE2239814C2 DE 2239814 C2 DE2239814 C2 DE 2239814C2 DE 2239814 A DE2239814 A DE 2239814A DE 2239814 A DE2239814 A DE 2239814A DE 2239814 C2 DE2239814 C2 DE 2239814C2
- Authority
- DE
- Germany
- Prior art keywords
- amino
- sulfonic acid
- phenyl
- methyl
- sulfonyl
- 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
- 239000000975 dye Substances 0.000 title description 18
- 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 description 2
- 239000002253 acid Substances 0.000 claims description 5
- -1 2-sulfoethyl Chemical group 0.000 description 59
- 239000000460 chlorine Substances 0.000 description 36
- 239000004952 Polyamide Substances 0.000 description 10
- 229920002647 polyamide Polymers 0.000 description 10
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 6
- 229960003080 taurine Drugs 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 238000004043 dyeing Methods 0.000 description 5
- 239000000835 fiber Substances 0.000 description 5
- 230000007935 neutral effect Effects 0.000 description 5
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 5
- QDHFHIQKOVNCNC-UHFFFAOYSA-N butane-1-sulfonic acid Chemical compound CCCCS(O)(=O)=O QDHFHIQKOVNCNC-UHFFFAOYSA-N 0.000 description 4
- 230000008878 coupling Effects 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 4
- 229950000244 sulfanilic acid Drugs 0.000 description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ZMCHBSMFKQYNKA-UHFFFAOYSA-N 2-aminobenzenesulfonic acid Chemical compound NC1=CC=CC=C1S(O)(=O)=O ZMCHBSMFKQYNKA-UHFFFAOYSA-N 0.000 description 3
- HZHMBNYJWQUCHI-UHFFFAOYSA-N 3-aminobutane-1-sulfonic acid Chemical compound CC(N)CCS(O)(=O)=O HZHMBNYJWQUCHI-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000012209 synthetic fiber Substances 0.000 description 3
- 229920002994 synthetic fiber Polymers 0.000 description 3
- WRZDSZXJYGDDBE-UHFFFAOYSA-N 2-phenoxybenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1OC1=CC=CC=C1 WRZDSZXJYGDDBE-UHFFFAOYSA-N 0.000 description 2
- SNKZJIOFVMKAOJ-UHFFFAOYSA-N 3-Aminopropanesulfonate Chemical compound NCCCS(O)(=O)=O SNKZJIOFVMKAOJ-UHFFFAOYSA-N 0.000 description 2
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 2
- KNILZINKISHVIQ-UHFFFAOYSA-N 4-azaniumylbutane-1-sulfonate Chemical compound NCCCCS(O)(=O)=O KNILZINKISHVIQ-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 239000002657 fibrous material Substances 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- HFLNYRDVMOCBPJ-UHFFFAOYSA-N sodium;amino(phenyl)methanesulfonic acid Chemical compound [Na+].OS(=O)(=O)C(N)C1=CC=CC=C1 HFLNYRDVMOCBPJ-UHFFFAOYSA-N 0.000 description 2
- QJGHJWKPZQIOSN-UHFFFAOYSA-N (4-aminophenyl)methanesulfonic acid Chemical compound NC1=CC=C(CS(O)(=O)=O)C=C1 QJGHJWKPZQIOSN-UHFFFAOYSA-N 0.000 description 1
- ZWUYCWUELHNHEX-UHFFFAOYSA-N 1-[(4-amino-2,5-dichlorophenyl)sulfonylamino]ethanesulfonic acid Chemical compound OS(=O)(=O)C(C)NS(=O)(=O)C1=CC(Cl)=C(N)C=C1Cl ZWUYCWUELHNHEX-UHFFFAOYSA-N 0.000 description 1
- NEKHWUVVKRUUIT-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-methylpyrazol-3-amine Chemical compound N1=C(C)C=C(N)N1C1=CC=CC=C1Cl NEKHWUVVKRUUIT-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- FJHGMUDVUAXUEK-UHFFFAOYSA-N 2-amino-4-methylbenzenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C(N)=C1 FJHGMUDVUAXUEK-UHFFFAOYSA-N 0.000 description 1
- FQBAMYDJEQUGNV-UHFFFAOYSA-N 2-methoxybenzenesulfonic acid Chemical compound COC1=CC=CC=C1S(O)(=O)=O FQBAMYDJEQUGNV-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- HAMSVUCKKOJYRA-UHFFFAOYSA-N 3-[(4-amino-2,5-dichlorophenyl)sulfonyl-methylamino]benzenesulfonic acid Chemical compound C=1C(Cl)=C(N)C=C(Cl)C=1S(=O)(=O)N(C)C1=CC=CC(S(O)(=O)=O)=C1 HAMSVUCKKOJYRA-UHFFFAOYSA-N 0.000 description 1
- SDLXCYOLWNWRRM-UHFFFAOYSA-N 3-[(4-amino-3-chlorophenyl)sulfonyl-ethylamino]propane-1-sulfonic acid Chemical compound OS(=O)(=O)CCCN(CC)S(=O)(=O)C1=CC=C(N)C(Cl)=C1 SDLXCYOLWNWRRM-UHFFFAOYSA-N 0.000 description 1
- DTNODBHGOLWROS-UHFFFAOYSA-N 3-amino-4-methylbenzenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1N DTNODBHGOLWROS-UHFFFAOYSA-N 0.000 description 1
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- JDQDSEVNMTYMOC-UHFFFAOYSA-N 3-methylbenzenesulfonic acid Chemical compound CC1=CC=CC(S(O)(=O)=O)=C1 JDQDSEVNMTYMOC-UHFFFAOYSA-N 0.000 description 1
- NEECEUZBAHTVIN-UHFFFAOYSA-N 4-amino-3-chlorobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1Cl NEECEUZBAHTVIN-UHFFFAOYSA-N 0.000 description 1
- GGEYQXPTJVTOMC-UHFFFAOYSA-N 5-[(4-amino-2,5-dichlorophenyl)sulfonyl-methylamino]-2-phenoxybenzenesulfonic acid Chemical compound C=1C(Cl)=C(N)C=C(Cl)C=1S(=O)(=O)N(C)C(C=C1S(O)(=O)=O)=CC=C1OC1=CC=CC=C1 GGEYQXPTJVTOMC-UHFFFAOYSA-N 0.000 description 1
- ATEVUDJJFBFBEP-UHFFFAOYSA-N 5-methyl-2-(3-nitrophenyl)pyrazol-3-amine Chemical compound N1=C(C)C=C(N)N1C1=CC=CC([N+]([O-])=O)=C1 ATEVUDJJFBFBEP-UHFFFAOYSA-N 0.000 description 1
- TVXCGEBTCKIPNH-UHFFFAOYSA-N 5-methyl-2-(4-nitrophenyl)pyrazol-3-amine Chemical compound N1=C(C)C=C(N)N1C1=CC=C([N+]([O-])=O)C=C1 TVXCGEBTCKIPNH-UHFFFAOYSA-N 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 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
- PWKULOLAYWPTES-UHFFFAOYSA-N Nc1cccc(c1Oc1ccccc1)S(O)(=O)=O Chemical compound Nc1cccc(c1Oc1ccccc1)S(O)(=O)=O PWKULOLAYWPTES-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- VTGXZHQPCOWGLK-UHFFFAOYSA-N [4-[(4-amino-2,5-dichlorophenyl)sulfonylamino]phenyl]methanesulfonic acid Chemical compound C1=C(Cl)C(N)=CC(Cl)=C1S(=O)(=O)NC1=CC=C(CS(O)(=O)=O)C=C1 VTGXZHQPCOWGLK-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- KERKSHQWMCWPBT-UHFFFAOYSA-N n-phenylacetamide;sulfurochloridic acid Chemical compound OS(Cl)(=O)=O.CC(=O)NC1=CC=CC=C1 KERKSHQWMCWPBT-UHFFFAOYSA-N 0.000 description 1
- NIXKBAZVOQAHGC-UHFFFAOYSA-N phenylmethanesulfonic acid Chemical compound OS(=O)(=O)CC1=CC=CC=C1 NIXKBAZVOQAHGC-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
- C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
- C09B29/3647—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms
- C09B29/3652—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles
- C09B29/3656—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles containing amino-1,2-diazoles
-
- 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
- C09B62/523—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 amido or hydroxyalkyl amino sulfonyl group, a quaternised or non-quaternised amino alkyl sulfonyl amido group, or a substituted alkyl amino sulfonyl group, or a halogen alkyl sulfonyl amido or halogen alkyl amino sulfonyl group or a vinyl sulfonylamido or a substituted vinyl sulfonamido group
- C09B62/527—Azo dyes
- C09B62/53—Monoazo dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2239814A DE2239814C2 (de) | 1972-08-12 | 1972-08-12 | Monoazofarbstoffe und ihre Verwendung |
| NL7311032A NL7311032A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-08-12 | 1973-08-09 | |
| JP48089356A JPS4945940A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-08-12 | 1973-08-10 | |
| GB3794973A GB1399585A (en) | 1972-08-12 | 1973-08-10 | Monoazo pyrazole dyestuffs |
| CH540775A CH569059A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-08-12 | 1973-08-10 | |
| US05/387,315 US4055557A (en) | 1972-08-12 | 1973-08-10 | Sulfonamidobenzene-azo-aminopyrazole dyestuffs |
| FR7329379A FR2195663B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-08-12 | 1973-08-10 | |
| IT27801/73A IT995319B (it) | 1972-08-12 | 1973-08-10 | Coloranti monoazoici |
| BE134457A BE803473A (fr) | 1972-08-12 | 1973-08-10 | Colorants monoazoiques |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2239814A DE2239814C2 (de) | 1972-08-12 | 1972-08-12 | Monoazofarbstoffe und ihre Verwendung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2239814A1 DE2239814A1 (de) | 1974-02-21 |
| DE2239814C2 true DE2239814C2 (de) | 1982-04-29 |
Family
ID=5853452
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2239814A Expired DE2239814C2 (de) | 1972-08-12 | 1972-08-12 | Monoazofarbstoffe und ihre Verwendung |
Country Status (9)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4159265A (en) * | 1973-07-14 | 1979-06-26 | Bayer Aktiengesellschaft | Phenylazopyrazolo dyestuffs including disulfimide substituent |
| JP4498044B2 (ja) * | 2003-09-18 | 2010-07-07 | 富士フイルム株式会社 | 新規なアゾ化合物を含む着色剤含有硬化性組成物、並びに、カラーフィルタおよびその製造方法 |
Family Cites Families (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1874474A (en) * | 1927-09-19 | 1932-08-30 | Gen Aniline Works Inc | Yellow azo dyestuff |
| US1893553A (en) * | 1928-05-26 | 1933-01-10 | Firm Chemical Works Formerly S | Manufacture of monoazo-dyestuffs |
| US1876884A (en) * | 1928-09-21 | 1932-09-13 | Gen Aniline Works Inc | Yellow pyrazolone mono azo dyestuffs |
| US2024864A (en) * | 1933-04-19 | 1935-12-17 | Cie Nat Matieres Colorantes | Chromatable azo dyestuffs and their production |
| US2015225A (en) * | 1933-12-01 | 1935-09-24 | Gen Aniline Works Inc | Azo-dyestuffs |
| US2152007A (en) * | 1934-01-31 | 1939-03-28 | Gen Aniline Works Inc | Azo dyestuffs and their production |
| US2073728A (en) * | 1934-07-17 | 1937-03-16 | Firm Chemical Works Formerly S | Process for the manufacture of chromatable azo dyestuffs of the pyrazolone series |
| US2220598A (en) * | 1938-06-04 | 1940-11-05 | Gen Aniline & Film Corp | Monoazo-dyestuffs insoluble in water |
| US2572394A (en) * | 1949-01-21 | 1951-10-23 | Sandoz Ag | Metallizable monoazo dyestuffs |
| US2788342A (en) * | 1951-12-15 | 1957-04-09 | Ciba Ltd | Cobaltiferous azo-dyestuffs |
| US2897189A (en) * | 1951-12-21 | 1959-07-28 | Ciba Ltd | Metalliferous azo-dyestuffs |
| US2789975A (en) * | 1953-05-22 | 1957-04-23 | Saul & Co | Azo dyestuffs of the pyrazolone series |
| CH324677A (de) * | 1954-04-21 | 1957-10-15 | Geigy Ag J R | Verfahren zur Herstellung von schwermetallhaltigen Azofarbstoffen |
| US3144437A (en) * | 1957-03-15 | 1964-08-11 | Sandoz Ag | Chromium and cobalt complex compounds of monoazo dyestuffs |
| US3136752A (en) * | 1957-10-23 | 1964-06-09 | Geigy Ag J R | Aminopyrazole monoazo dyestuffs |
| DE1100846B (de) * | 1957-10-23 | 1961-03-02 | Geigy Ag J R | Verfahren zur Herstellung von Monoazofarbstoffen |
| FR1214975A (fr) * | 1957-10-23 | 1960-04-13 | Geigy Ag J R | Colorants mono-azoïques, leur préparation et leurs applications |
| GB868474A (en) * | 1959-03-03 | 1961-05-17 | Geigy Ag J R | Improvements relating to monoazo-pyrazole dyestuffs and their use |
| DE1130949B (de) * | 1959-03-03 | 1962-06-07 | Geigy Ag J R | Verfahren zur Herstellung von Monoazofarbstoffen |
| CH373842A (de) * | 1959-09-11 | 1963-12-15 | Geigy Ag J R | Verfahren zur Herstellung von in Wasser dispergierbaren, schwer löslichen Azofarbstoffen |
| CH386028A (de) * | 1960-05-12 | 1964-12-31 | Geigy Ag J R | Verfahren zur Herstellung von neuen schwermetallhaltigen Formazanfarbstoffen |
| DE1150769B (de) * | 1960-06-22 | 1963-06-27 | Bayer Ag | Verfahren zur Herstellung von Azofarbstoffen |
| CH419388A (de) * | 1962-08-02 | 1966-08-31 | Geigy Ag J R | Verfahren zur Herstellung von in Wasser schwerlöslichen Azofarbstoffen |
| BE643924A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1963-02-22 | 1964-06-15 | ||
| DE1239421B (de) * | 1963-11-15 | 1967-04-27 | Bayer Ag | Verfahren zur Herstellung von Azofarbstoffen |
| DE1289930B (de) * | 1964-09-24 | 1969-02-27 | Hoechst Ag | Verfahren zur Herstellung von Azofarbstoffen und deren Metallkomplexverbindungen |
| US3379715A (en) * | 1964-12-30 | 1968-04-23 | Gen Aniline & Film Corp | Monoazo pyrazolone dyestuffs |
| CH471199A (de) * | 1965-07-06 | 1969-04-15 | Sandoz Ag | Verfahren zur Herstellung metallhaltiger Azofarbstoffe |
| US3528961A (en) * | 1966-08-16 | 1970-09-15 | Allied Chem | Monoazo dyes from e-caprolactam |
| CH481187A (de) * | 1966-10-14 | 1969-11-15 | Sandoz Ag | Verfahren zur Herstellung von Reaktivfarbstoffen |
| GB1220422A (en) * | 1968-02-28 | 1971-01-27 | Sumitomo Chemical Co | Reactive yellow monoazo dyes of the phenylazo-pyrazole series and process for the preparation thereof |
-
1972
- 1972-08-12 DE DE2239814A patent/DE2239814C2/de not_active Expired
-
1973
- 1973-08-09 NL NL7311032A patent/NL7311032A/xx not_active Application Discontinuation
- 1973-08-10 BE BE134457A patent/BE803473A/xx unknown
- 1973-08-10 FR FR7329379A patent/FR2195663B1/fr not_active Expired
- 1973-08-10 GB GB3794973A patent/GB1399585A/en not_active Expired
- 1973-08-10 CH CH540775A patent/CH569059A5/xx not_active IP Right Cessation
- 1973-08-10 IT IT27801/73A patent/IT995319B/it active
- 1973-08-10 JP JP48089356A patent/JPS4945940A/ja active Pending
- 1973-08-10 US US05/387,315 patent/US4055557A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4945940A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-05-02 |
| US4055557A (en) | 1977-10-25 |
| CH569059A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-11-14 |
| GB1399585A (en) | 1975-07-02 |
| DE2239814A1 (de) | 1974-02-21 |
| IT995319B (it) | 1975-11-10 |
| FR2195663B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-09-23 |
| NL7311032A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-02-14 |
| FR2195663A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-03-08 |
| BE803473A (fr) | 1974-02-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| D2 | Grant after examination | ||
| 8339 | Ceased/non-payment of the annual fee |