DE2702584C2 - Konzentrierte wäßrige oder wäßrig-organische Lösungen von Acetoacetylaminoarylsulfonsäuresalzen, Verfahren zu deren Herstellung und Verfahren zur Herstellung von konzentrierten Lösungen sulfonsäuregruppenhaltiger Azofarbstoffe aus den vorgenannten Lösungen - Google Patents
Konzentrierte wäßrige oder wäßrig-organische Lösungen von Acetoacetylaminoarylsulfonsäuresalzen, Verfahren zu deren Herstellung und Verfahren zur Herstellung von konzentrierten Lösungen sulfonsäuregruppenhaltiger Azofarbstoffe aus den vorgenannten LösungenInfo
- Publication number
- DE2702584C2 DE2702584C2 DE2702584A DE2702584A DE2702584C2 DE 2702584 C2 DE2702584 C2 DE 2702584C2 DE 2702584 A DE2702584 A DE 2702584A DE 2702584 A DE2702584 A DE 2702584A DE 2702584 C2 DE2702584 C2 DE 2702584C2
- Authority
- DE
- Germany
- Prior art keywords
- solutions
- aqueous
- preparation
- concentrated
- processes
- 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
- 239000002253 acid Substances 0.000 title claims description 23
- 150000003839 salts Chemical class 0.000 title claims description 7
- 239000007864 aqueous solution Substances 0.000 title claims description 3
- 239000002152 aqueous-organic solution Substances 0.000 title claims description 3
- 239000000243 solution Substances 0.000 title description 45
- 238000000034 method Methods 0.000 title description 8
- 238000002360 preparation method Methods 0.000 title description 6
- 239000000987 azo dye Substances 0.000 title description 5
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 title 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 239000000975 dye Substances 0.000 description 29
- -1 carboxycarbonylamino Chemical group 0.000 description 17
- 150000001412 amines Chemical class 0.000 description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000007983 Tris buffer Substances 0.000 description 9
- 239000012954 diazonium Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 9
- 150000002500 ions Chemical class 0.000 description 9
- 238000005859 coupling reaction Methods 0.000 description 8
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 8
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 7
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 7
- 229960003237 betaine Drugs 0.000 description 7
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 6
- 230000008878 coupling Effects 0.000 description 6
- 238000010168 coupling process Methods 0.000 description 6
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical class C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 125000000542 sulfonic acid group Chemical group 0.000 description 4
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- 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 2
- PPVRMPPLECDING-UHFFFAOYSA-N 4-[(4-aminophenyl)diazenyl]benzenesulfonic acid Chemical compound C1=CC(N)=CC=C1N=NC1=CC=C(S(O)(=O)=O)C=C1 PPVRMPPLECDING-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 238000006193 diazotization reaction Methods 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910001415 sodium ion Inorganic materials 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
- SVFILEBAODPXOT-UHFFFAOYSA-N 2-(2-aminophenyl)-6-methyl-1,3-benzothiazole-7-sulfonic acid Chemical compound S1C2=C(S(O)(=O)=O)C(C)=CC=C2N=C1C1=CC=CC=C1N SVFILEBAODPXOT-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- SBPQKRDZOWFQJU-UHFFFAOYSA-N 2-(4-amino-2-sulfoanilino)-2-oxoacetic acid Chemical compound NC1=CC=C(NC(=O)C(O)=O)C(S(O)(=O)=O)=C1 SBPQKRDZOWFQJU-UHFFFAOYSA-N 0.000 description 1
- KKFDCBRMNNSAAW-UHFFFAOYSA-N 2-(morpholin-4-yl)ethanol Chemical compound OCCN1CCOCC1 KKFDCBRMNNSAAW-UHFFFAOYSA-N 0.000 description 1
- KZTWONRVIPPDKH-UHFFFAOYSA-N 2-(piperidin-1-yl)ethanol Chemical compound OCCN1CCCCC1 KZTWONRVIPPDKH-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-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
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
- PEKNMAYVYOCAAE-UHFFFAOYSA-N 3-(ethoxyamino)benzenesulfonic acid Chemical compound CCONC1=CC=CC(S(O)(=O)=O)=C1 PEKNMAYVYOCAAE-UHFFFAOYSA-N 0.000 description 1
- LPYLJONZZIGQPQ-UHFFFAOYSA-N 3-amino-4-chloro-2-methylbenzenesulfonic acid Chemical compound CC1=C(N)C(Cl)=CC=C1S(O)(=O)=O LPYLJONZZIGQPQ-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
- 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
- PRLIMMHXFBMDPL-UHFFFAOYSA-N 4-(3-oxobutanoylamino)naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(NC(=O)CC(=O)C)=CC=C(S(O)(=O)=O)C2=C1 PRLIMMHXFBMDPL-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
- 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
- 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
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 1
- QUFFRITXLMVPMV-UHFFFAOYSA-N 4-aminonaphthalene-1,6-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 QUFFRITXLMVPMV-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
- BRKFTWHPLMMNHF-UHFFFAOYSA-N 5-amino-2-methylbenzenesulfonic acid Chemical compound CC1=CC=C(N)C=C1S(O)(=O)=O BRKFTWHPLMMNHF-UHFFFAOYSA-N 0.000 description 1
- IZNPFDIKQHGNSK-UHFFFAOYSA-N 5-amino-6-ethoxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=CC2=C(N)C(OCC)=CC=C21 IZNPFDIKQHGNSK-UHFFFAOYSA-N 0.000 description 1
- KZCSUEYBKAPKNH-UHFFFAOYSA-N 6-aminonaphthalene-1,3-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KZCSUEYBKAPKNH-UHFFFAOYSA-N 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- 229910004072 SiFe Inorganic materials 0.000 description 1
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000002339 acetoacetyl group Chemical group O=C([*])C([H])([H])C(=O)C([H])([H])[H] 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 230000003139 buffering effect Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 1
- 150000001987 diarylethers Chemical class 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229940102253 isopropanolamine Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- UCFFGYASXIPWPD-UHFFFAOYSA-N methyl hypochlorite Chemical group COCl UCFFGYASXIPWPD-UHFFFAOYSA-N 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- NRZRRZAVMCAKEP-UHFFFAOYSA-N naphthionic acid Chemical compound C1=CC=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 NRZRRZAVMCAKEP-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003852 triazoles 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0003—Monoazo dyes prepared by diazotising and coupling from diazotized anilines
- C09B29/0011—Monoazo dyes prepared by diazotising and coupling from diazotized anilines from diazotized anilines directly substituted by a heterocyclic ring (not condensed)
-
- 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
- C09B29/32—Monoazo dyes prepared by diazotising and coupling from coupling components containing a reactive methylene group
- C09B29/33—Aceto- or benzoylacetylarylides
- C09B29/331—Aceto- or benzoylacetylarylides containing acid groups, e.g. COOH, SO3H, PO3H2, OSO3H2, OPO2H2; salts thereof
- C09B29/332—Carbocyclic arylides
-
- 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
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
- C09B31/02—Disazo dyes
- C09B31/10—Disazo dyes from a coupling component "C" containing reactive methylene groups
- C09B31/11—Aceto- or benzoyl-acetylarylides
- C09B31/115—Aceto- or benzoyl-acetylarylides containing acid groups, e.g. -COOH, -SO3H, -PO3H2, -OSO3H, -OPO2H2; salts thereof
-
- 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
- C09B33/00—Disazo and polyazo dyes of the types A->K<-B, A->B->K<-C, or the like, prepared by diazotising and coupling
- C09B33/02—Disazo dyes
-
- 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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0072—Preparations with anionic dyes or reactive dyes
- C09B67/0073—Preparations of acid or reactive dyes in liquid form
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S534/00—Organic compounds -- part of the class 532-570 series
- Y10S534/01—Mixtures of azo compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring (AREA)
- Paper (AREA)
- Detergent Compositions (AREA)
- Cephalosporin Compounds (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2702584A DE2702584C2 (de) | 1977-01-22 | 1977-01-22 | Konzentrierte wäßrige oder wäßrig-organische Lösungen von Acetoacetylaminoarylsulfonsäuresalzen, Verfahren zu deren Herstellung und Verfahren zur Herstellung von konzentrierten Lösungen sulfonsäuregruppenhaltiger Azofarbstoffe aus den vorgenannten Lösungen |
| GB2007/78A GB1574400A (en) | 1977-01-22 | 1978-01-18 | Concentrated aqueous solutions of salts of acetoacetyl-amino-arylsulphonic acids |
| US05/870,602 US4399068A (en) | 1977-01-22 | 1978-01-18 | Concentrated, aqueous solutions of salts of acetoacetylamino-arylsulphonic acids and method of forming concentrated solutions of azo dyestuffs therefrom |
| BR7800324A BR7800324A (pt) | 1977-01-22 | 1978-01-19 | Sais de acido acetoacetilamino-arilsulfonico,solucao aquosa concentrada,processo para obtencao dos ditos sais,processo para preparacao de solucoes concentradas de corantes azoicos contendo grupos de acido sulfonicos,e solucao concentrada de corante |
| CH58478A CH634296A5 (de) | 1977-01-22 | 1978-01-19 | Acetoacetylamino-arylsulfonsaeuresalze sowie verfahren zu deren herstellung. |
| FR7801625A FR2378003A1 (fr) | 1977-01-22 | 1978-01-20 | Solutions aqueuses concentrees de sels d'acides acetylacetylaminoarylsulfoniques et leur application a la preparation de colorants azoiques anioniques |
| IT7819498A IT7819498A0 (it) | 1977-01-22 | 1978-01-20 | Soluzioni acquose, concentrate di sali di acisi acetoacetilamino aril solfonici. |
| ES466195A ES466195A1 (es) | 1977-01-22 | 1978-01-20 | Procedimiento para la obtencion de sales del acido acetoace-tilamino-arilsufonico y sus soluciones acuosas concentradas. |
| JP53004427A JPS6016930B2 (ja) | 1977-01-22 | 1978-01-20 | アセトアセチルアミノ−アリ−ルスルホン酸塩および製造法 |
| BE184474A BE863112A (fr) | 1977-01-22 | 1978-01-20 | Solutions aqueuses concentrees de sels d'acides acetylacetylaminoarylsulfoniques |
| JP59177620A JPS60123558A (ja) | 1977-01-22 | 1984-08-28 | アゾ染料の濃溶液およびその製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2702584A DE2702584C2 (de) | 1977-01-22 | 1977-01-22 | Konzentrierte wäßrige oder wäßrig-organische Lösungen von Acetoacetylaminoarylsulfonsäuresalzen, Verfahren zu deren Herstellung und Verfahren zur Herstellung von konzentrierten Lösungen sulfonsäuregruppenhaltiger Azofarbstoffe aus den vorgenannten Lösungen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2702584A1 DE2702584A1 (de) | 1978-07-27 |
| DE2702584C2 true DE2702584C2 (de) | 1982-10-14 |
Family
ID=5999286
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2702584A Expired DE2702584C2 (de) | 1977-01-22 | 1977-01-22 | Konzentrierte wäßrige oder wäßrig-organische Lösungen von Acetoacetylaminoarylsulfonsäuresalzen, Verfahren zu deren Herstellung und Verfahren zur Herstellung von konzentrierten Lösungen sulfonsäuregruppenhaltiger Azofarbstoffe aus den vorgenannten Lösungen |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4399068A (en, 2012) |
| JP (2) | JPS6016930B2 (en, 2012) |
| BE (1) | BE863112A (en, 2012) |
| BR (1) | BR7800324A (en, 2012) |
| CH (1) | CH634296A5 (en, 2012) |
| DE (1) | DE2702584C2 (en, 2012) |
| ES (1) | ES466195A1 (en, 2012) |
| FR (1) | FR2378003A1 (en, 2012) |
| GB (1) | GB1574400A (en, 2012) |
| IT (1) | IT7819498A0 (en, 2012) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2949517A1 (de) * | 1979-12-08 | 1981-06-25 | Bayer Ag, 5090 Leverkusen | Konzentrierte waessrige loesungen von monoazofarbstoffen und deren verwendung zum faerben von papier |
| DE3219651A1 (de) * | 1982-05-26 | 1983-12-01 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung von n-acetylaminoarylsulfonsaeuren |
| DE3853171D1 (de) * | 1987-03-27 | 1995-04-06 | Ciba Geigy Ag | Kationische Azofarbstoffe. |
| DE3735078A1 (de) * | 1987-10-16 | 1989-04-27 | Cassella Ag | Wasserloesliche gelbe monoazofarbstoffe |
| US4968352A (en) * | 1988-04-28 | 1990-11-06 | Hoechst Celanese Corporation | Diaryl pigments with improved heat stability and transparency containing coupled mixed bis-diazotized diamines and acid-substituted aromatic amines |
| DE58909267D1 (de) * | 1988-11-15 | 1995-07-06 | Ciba Geigy Ag | Konzentrierte Farbstofflösungen. |
| DE59206989D1 (de) * | 1991-08-08 | 1996-10-02 | Ciba Geigy Ag | Farbstoffe, Verfahren zu deren Herstellung und deren Verwendung |
| GB0106345D0 (en) * | 2001-03-14 | 2001-05-02 | Avecia Ltd | Compounds compositions and processes |
| US20070226920A1 (en) * | 2004-04-27 | 2007-10-04 | Gregoire Folly | Salts of Laked Monoazo Compounds |
| US8328925B2 (en) * | 2007-05-23 | 2012-12-11 | Clariant Finance (Bvi) Limited | Stable liquid formulation |
| ES2732327T3 (es) | 2014-03-28 | 2019-11-21 | Archroma Ip Gmbh | Disoluciones de tinte estables al almacenamiento |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2328353A (en) * | 1941-06-07 | 1943-08-31 | American Cyanamid Co | Azo dyestuff intermediate |
| US2310181A (en) * | 1941-06-07 | 1943-02-02 | American Cyanamid Co | Azo dyestuffs |
| US3274171A (en) * | 1963-04-29 | 1966-09-20 | Allied Chem | Monoazo dyestuffs containing a benzothiazole nucleus |
| US3313665A (en) * | 1963-06-04 | 1967-04-11 | American Filtrona Corp | Method for making fibrous bodies |
| DE2051303C3 (de) * | 1970-10-20 | 1978-12-21 | Bayer Ag, 5090 Leverkusen | Polyhydroxyalkylaminsalze anionischer Farbstoffe |
| CH556902A (de) * | 1970-10-22 | 1974-12-13 | Ciba Geigy Ag | Verfahren zur herstellung von farbstoffen in form von stabilen konzentrierten loesungen oder dispersionen. |
| CH554397A (de) * | 1971-02-16 | 1974-09-30 | Sandoz Ag | Verfahren zur herstellung von azofarbstoffen. |
| DE2126299C3 (de) * | 1971-05-27 | 1975-02-13 | Bayer Ag, 5090 Leverkusen | Phenyl-naphthotrlazolmonoazofarbstoffe, deren Herstellung und Verwendung |
| DE2230073A1 (de) * | 1971-06-25 | 1972-12-28 | Unilever N.V., Rotterdam (Niederlande) | alpha-substituierte beta-Sulfobernsteinsäuren und ihre Verwendung als Builder in Waschmitteln |
| NL171267C (nl) * | 1975-12-19 | Ciba Geigy | Werkwijze voor het bereiden van gefluoreerde sulfonzuren en zouten daarvan, alsmede werkwijze voor het bereiden van samenstellingen, die deze verbindingen bevatten. |
-
1977
- 1977-01-22 DE DE2702584A patent/DE2702584C2/de not_active Expired
-
1978
- 1978-01-18 GB GB2007/78A patent/GB1574400A/en not_active Expired
- 1978-01-18 US US05/870,602 patent/US4399068A/en not_active Expired - Lifetime
- 1978-01-19 BR BR7800324A patent/BR7800324A/pt unknown
- 1978-01-19 CH CH58478A patent/CH634296A5/de not_active IP Right Cessation
- 1978-01-20 FR FR7801625A patent/FR2378003A1/fr active Granted
- 1978-01-20 IT IT7819498A patent/IT7819498A0/it unknown
- 1978-01-20 BE BE184474A patent/BE863112A/xx unknown
- 1978-01-20 JP JP53004427A patent/JPS6016930B2/ja not_active Expired
- 1978-01-20 ES ES466195A patent/ES466195A1/es not_active Expired
-
1984
- 1984-08-28 JP JP59177620A patent/JPS60123558A/ja active Pending
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
Also Published As
| Publication number | Publication date |
|---|---|
| US4399068A (en) | 1983-08-16 |
| ES466195A1 (es) | 1978-10-01 |
| DE2702584A1 (de) | 1978-07-27 |
| IT7819498A0 (it) | 1978-01-20 |
| FR2378003B1 (en, 2012) | 1983-09-09 |
| GB1574400A (en) | 1980-09-03 |
| CH634296A5 (de) | 1983-01-31 |
| JPS60123558A (ja) | 1985-07-02 |
| FR2378003A1 (fr) | 1978-08-18 |
| JPS6016930B2 (ja) | 1985-04-30 |
| JPS5392734A (en) | 1978-08-15 |
| BR7800324A (pt) | 1978-09-05 |
| BE863112A (fr) | 1978-07-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1050940B (de) | Verfahren zur Herstellung von Farbsalzen | |
| DE2702584C2 (de) | Konzentrierte wäßrige oder wäßrig-organische Lösungen von Acetoacetylaminoarylsulfonsäuresalzen, Verfahren zu deren Herstellung und Verfahren zur Herstellung von konzentrierten Lösungen sulfonsäuregruppenhaltiger Azofarbstoffe aus den vorgenannten Lösungen | |
| DE942345C (de) | Verfahren zur Herstellung neuer direktziehender Azofarbstoffe | |
| DE2531445C3 (de) | Sulfogruppenfreie wasserlösliche Azofarbstoffe und deren Verwendung zum Färben und/oder Bedrucken von synthetischen Textilfasern | |
| CH524673A (de) | Verfahren zur Herstellung von wasserlöslichen Disazofarbstoffen | |
| DE2349457A1 (de) | Wasserloesliche monoazofarbstoffe | |
| DE3329193A1 (de) | Verfahren zum faerben von amidgruppenhaltigen fasermaterialien | |
| EP0062824A2 (de) | Sulfonsäuregruppenhaltige kationische Azofarbstoffe, ihre Herstellung und ihre Verwendung | |
| DE2630988A1 (de) | Azofarbstoffe | |
| DE2126299C3 (de) | Phenyl-naphthotrlazolmonoazofarbstoffe, deren Herstellung und Verwendung | |
| DE2822318A1 (de) | Disazoharnstoffarbstoff-loesungen und verfahren zu ihrer herstellung | |
| DE964974C (de) | Verfahren zur Herstellung von Mono- und Disazofarbstoffen | |
| DE2541007A1 (de) | Wasserloesliche trisazofarbstoffe, ihre herstellung und verwendung | |
| DE964975C (de) | Verfahren zur Herstellung von Monoazofarbstoffen | |
| CH615693A5 (en) | Process for preparing new trisazo dyes, the trisazo dyes and use thereof | |
| DE1960816C3 (de) | Sulfonsäureestergruppenhaltige Disazofarbstoffe | |
| DE845085C (de) | Verfahren zur Herstellung unsymmetrischer Harnstoffderivate von Aminoazofarbstoffen | |
| DE1019025B (de) | Verfahren zur Herstellung von Monoazofarbstoffen | |
| DE962797C (de) | Verfahren zur Herstellung von o-Oxy-diazoverbindungen der Naphthalinreihe | |
| DE1644215C3 (de) | Wasserlösliche Monoazofarbstoffe, ein Verfahren zu ihrer Herstellung und ihre Verwendung | |
| DE3221504A1 (de) | Wasserunloesliche monoazofarbstoffe, ihre herstellung und ihre verwendung | |
| DE842098C (de) | Verfahren zur Herstellung von metallisierbaren Dis- oder Polyazofarbstoffen der Dipyrazolonreihe | |
| DE1960816A1 (de) | Disazofarbstoffe | |
| DE1944699A1 (de) | Monoazofarbstoffe | |
| DE1221746B (de) | Verfahren zur Herstellung wasserunloeslicher Monoazofarbstoffe |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OAP | Request for examination filed | ||
| OD | Request for examination | ||
| D2 | Grant after examination | ||
| 8339 | Ceased/non-payment of the annual fee |