DE2049620C3 - Stabile, konzentrierte, saure Stammlösungen von anionischen Farbstoffen, Verfahren zu ihrer Herstellung und ihre Verwendung - Google Patents
Stabile, konzentrierte, saure Stammlösungen von anionischen Farbstoffen, Verfahren zu ihrer Herstellung und ihre VerwendungInfo
- Publication number
- DE2049620C3 DE2049620C3 DE19702049620 DE2049620A DE2049620C3 DE 2049620 C3 DE2049620 C3 DE 2049620C3 DE 19702049620 DE19702049620 DE 19702049620 DE 2049620 A DE2049620 A DE 2049620A DE 2049620 C3 DE2049620 C3 DE 2049620C3
- Authority
- DE
- Germany
- Prior art keywords
- parts
- acid
- water
- formic acid
- solution
- 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 claims description 94
- 238000002360 preparation method Methods 0.000 title claims description 9
- 239000011550 stock solution Substances 0.000 title description 71
- 238000000034 method Methods 0.000 title description 20
- 230000002378 acidificating effect Effects 0.000 title description 14
- 230000008569 process Effects 0.000 title description 11
- 125000000129 anionic group Chemical group 0.000 title description 3
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 263
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 133
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 131
- 235000019253 formic acid Nutrition 0.000 claims description 131
- 239000000203 mixture Substances 0.000 claims description 79
- 239000002253 acid Substances 0.000 claims description 70
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 58
- 235000019260 propionic acid Nutrition 0.000 claims description 29
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 29
- 150000007513 acids Chemical class 0.000 claims description 10
- 239000000843 powder Substances 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 9
- 239000011877 solvent mixture Substances 0.000 claims description 8
- 239000000654 additive Substances 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 5
- 150000003863 ammonium salts Chemical class 0.000 claims description 4
- 239000000987 azo dye Substances 0.000 claims description 4
- 235000011054 acetic acid Nutrition 0.000 claims description 2
- 238000004040 coloring Methods 0.000 claims description 2
- 239000000428 dust Substances 0.000 claims description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims 1
- 241000953561 Toia Species 0.000 claims 1
- 238000005054 agglomeration Methods 0.000 claims 1
- 230000002776 aggregation Effects 0.000 claims 1
- 238000010410 dusting Methods 0.000 claims 1
- 230000003179 granulation Effects 0.000 claims 1
- 238000005469 granulation Methods 0.000 claims 1
- 230000001771 impaired effect Effects 0.000 claims 1
- 239000000243 solution Substances 0.000 description 112
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 78
- 238000003756 stirring Methods 0.000 description 62
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 45
- BPNMDHFDBYBRBV-UHFFFAOYSA-N 1-(1-nitrosooxypropan-2-yloxy)propan-2-yl nitrite Chemical compound N(=O)OC(C)COC(C)CON=O BPNMDHFDBYBRBV-UHFFFAOYSA-N 0.000 description 40
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 34
- 238000005859 coupling reaction Methods 0.000 description 28
- 238000006243 chemical reaction Methods 0.000 description 27
- 230000008878 coupling Effects 0.000 description 26
- 238000010168 coupling process Methods 0.000 description 26
- -1 alkyl nitrite Chemical compound 0.000 description 25
- 238000001914 filtration Methods 0.000 description 21
- 229950000244 sulfanilic acid Drugs 0.000 description 18
- 150000003839 salts Chemical class 0.000 description 14
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 description 13
- 238000005352 clarification Methods 0.000 description 13
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 12
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 12
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical class ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 11
- 239000000725 suspension Substances 0.000 description 11
- 238000006193 diazotization reaction Methods 0.000 description 10
- 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 10
- IOCXECKVGHWRNH-UHFFFAOYSA-N 2-phenylindole-2-sulfonic acid Chemical compound C1=C2C=CC=CC2=NC1(S(=O)(=O)O)C1=CC=CC=C1 IOCXECKVGHWRNH-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 8
- 238000007792 addition Methods 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 8
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
- GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 7
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 238000003860 storage Methods 0.000 description 7
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 7
- ZMCHBSMFKQYNKA-UHFFFAOYSA-N 2-aminobenzenesulfonic acid Chemical compound NC1=CC=CC=C1S(O)(=O)=O ZMCHBSMFKQYNKA-UHFFFAOYSA-N 0.000 description 6
- JCUYNPHEESTECG-UHFFFAOYSA-N 3-amino-6-(4-aminophenyl)benzene-1,2-disulfonic acid Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C(S(O)(=O)=O)=C1S(O)(=O)=O JCUYNPHEESTECG-UHFFFAOYSA-N 0.000 description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 241000257303 Hymenoptera Species 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 230000008034 disappearance Effects 0.000 description 6
- 238000004043 dyeing Methods 0.000 description 6
- NDYALMUZRGNFLU-UHFFFAOYSA-N (2-aminophenyl)methanesulfonic acid Chemical compound NC1=CC=CC=C1CS(O)(=O)=O NDYALMUZRGNFLU-UHFFFAOYSA-N 0.000 description 5
- FAFQZAMHELSOOA-UHFFFAOYSA-N 2-nitrosooxyethyl nitrite Chemical compound O=NOCCON=O FAFQZAMHELSOOA-UHFFFAOYSA-N 0.000 description 5
- QUPZPYRXBYXPLN-UHFFFAOYSA-N 4-(aminodiazenyl)benzenesulfonic acid Chemical compound NN=NC1=CC=C(S(O)(=O)=O)C=C1 QUPZPYRXBYXPLN-UHFFFAOYSA-N 0.000 description 5
- CQPFMGBJSMSXLP-ZAGWXBKKSA-M Acid orange 7 Chemical compound OC1=C(C2=CC=CC=C2C=C1)/N=N/C1=CC=C(C=C1)S(=O)(=O)[O-].[Na+] CQPFMGBJSMSXLP-ZAGWXBKKSA-M 0.000 description 5
- DYRDKSSFIWVSNM-UHFFFAOYSA-N acetoacetanilide Chemical class CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 description 5
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 5
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 5
- 125000000542 sulfonic acid group Chemical group 0.000 description 5
- CZZZABOKJQXEBO-UHFFFAOYSA-N 2,4-dimethylaniline Chemical compound CC1=CC=C(N)C(C)=C1 CZZZABOKJQXEBO-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 4
- CQPFMGBJSMSXLP-UHFFFAOYSA-M acid orange 7 Chemical compound [Na+].OC1=CC=C2C=CC=CC2=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 CQPFMGBJSMSXLP-UHFFFAOYSA-M 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- WPWNIQBSYQVEKJ-UHFFFAOYSA-M chembl2028451 Chemical compound [Na+].CC1=CC(S([O-])(=O)=O)=CC=C1N=NC1=C(O)C=CC2=CC=CC=C12 WPWNIQBSYQVEKJ-UHFFFAOYSA-M 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 235000010288 sodium nitrite Nutrition 0.000 description 4
- IKAHFTWDTODWID-UHFFFAOYSA-N 2-hydroxyethylazanium;formate Chemical compound [O-]C=O.[NH3+]CCO IKAHFTWDTODWID-UHFFFAOYSA-N 0.000 description 3
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 150000001447 alkali salts Chemical class 0.000 description 3
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 230000006378 damage Effects 0.000 description 3
- 150000002334 glycols Chemical class 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 150000002823 nitrates Chemical class 0.000 description 3
- 239000001272 nitrous oxide Substances 0.000 description 3
- 239000000123 paper Substances 0.000 description 3
- WPWNIQBSYQVEKJ-UHFFFAOYSA-N sodium 4-[(2-hydroxynaphthalen-1-yl)diazenyl]-3-methylbenzenesulfonic acid Chemical compound [Na+].CC1=CC(S(O)(=O)=O)=CC=C1N=NC1=C(O)C=CC2=CC=CC=C12 WPWNIQBSYQVEKJ-UHFFFAOYSA-N 0.000 description 3
- 239000004753 textile Substances 0.000 description 3
- QJGHJWKPZQIOSN-UHFFFAOYSA-N (4-aminophenyl)methanesulfonic acid Chemical compound NC1=CC=C(CS(O)(=O)=O)C=C1 QJGHJWKPZQIOSN-UHFFFAOYSA-N 0.000 description 2
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 2
- GVBHRNIWBGTNQA-UHFFFAOYSA-N 2-methoxy-4-nitroaniline Chemical compound COC1=CC([N+]([O-])=O)=CC=C1N GVBHRNIWBGTNQA-UHFFFAOYSA-N 0.000 description 2
- QPQKUYVSJWQSDY-CCEZHUSRSA-N 4-(phenylazo)aniline Chemical compound C1=CC(N)=CC=C1\N=N\C1=CC=CC=C1 QPQKUYVSJWQSDY-CCEZHUSRSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- 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 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 241001122767 Theaceae Species 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N anhydrous trimethylamine Natural products CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 239000002518 antifoaming agent Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000976 ink Substances 0.000 description 2
- JJYPMNFTHPTTDI-UHFFFAOYSA-N meta-toluidine Natural products CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
- CHMBIJAOCISYEW-UHFFFAOYSA-N n-(4-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=C(N)C=C1 CHMBIJAOCISYEW-UHFFFAOYSA-N 0.000 description 2
- KUDPGZONDFORKU-UHFFFAOYSA-N n-chloroaniline Chemical compound ClNC1=CC=CC=C1 KUDPGZONDFORKU-UHFFFAOYSA-N 0.000 description 2
- OENHRRVNRZBNNS-UHFFFAOYSA-N naphthalene-1,8-diol Chemical compound C1=CC(O)=C2C(O)=CC=CC2=C1 OENHRRVNRZBNNS-UHFFFAOYSA-N 0.000 description 2
- DFQICHCWIIJABH-UHFFFAOYSA-N naphthalene-2,7-diol Chemical compound C1=CC(O)=CC2=CC(O)=CC=C21 DFQICHCWIIJABH-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- RNVCVTLRINQCPJ-UHFFFAOYSA-N ortho-methyl aniline Natural products CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- LGZQSRCLLIPAEE-UHFFFAOYSA-M sodium 1-[(4-sulfonaphthalen-1-yl)diazenyl]naphthalen-2-olate Chemical compound [Na+].C1=CC=C2C(N=NC3=C4C=CC=CC4=CC=C3O)=CC=C(S([O-])(=O)=O)C2=C1 LGZQSRCLLIPAEE-UHFFFAOYSA-M 0.000 description 2
- COEZWFYORILMOM-UHFFFAOYSA-M sodium 4-[(2,4-dihydroxyphenyl)diazenyl]benzenesulfonate Chemical compound [Na+].OC1=CC(O)=CC=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 COEZWFYORILMOM-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 2
- 239000002351 wastewater Substances 0.000 description 2
- 239000003021 water soluble solvent Substances 0.000 description 2
- NDGVYNGMDFNLJP-UHFFFAOYSA-N (4-amino-2-chlorophenyl)methanesulfonic acid Chemical compound NC1=CC(=C(C=C1)CS(=O)(=O)O)Cl NDGVYNGMDFNLJP-UHFFFAOYSA-N 0.000 description 1
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-dioxonaphthalene Natural products C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 1
- BOKGTLAJQHTOKE-UHFFFAOYSA-N 1,5-dihydroxynaphthalene Chemical compound C1=CC=C2C(O)=CC=CC2=C1O BOKGTLAJQHTOKE-UHFFFAOYSA-N 0.000 description 1
- UEOSSNCIMMVUQH-UHFFFAOYSA-N 1,8-dihydroxy-2h-naphthalene-1,2-disulfonic acid Chemical compound C1=CC(S(O)(=O)=O)C(O)(S(O)(=O)=O)C2=C1C=CC=C2O UEOSSNCIMMVUQH-UHFFFAOYSA-N 0.000 description 1
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 1
- QPXGLRJFCBZQNF-UHFFFAOYSA-N 1-[3-(hydroxymethyl)phenyl]-2-[(2-phenylmethoxyphenyl)methylamino]ethanol Chemical group OCC1=CC=CC(C(O)CNCC=2C(=CC=CC=2)OCC=2C=CC=CC=2)=C1 QPXGLRJFCBZQNF-UHFFFAOYSA-N 0.000 description 1
- HGVJHAMFCVPSRK-UHFFFAOYSA-N 1-hydroxy-2h-naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(O)(S(O)(=O)=O)CC=CC2=C1 HGVJHAMFCVPSRK-UHFFFAOYSA-N 0.000 description 1
- NDDCMXAQYSJHDC-UHFFFAOYSA-N 1-nitrosooxypropan-2-yl nitrite Chemical compound O=NOC(C)CON=O NDDCMXAQYSJHDC-UHFFFAOYSA-N 0.000 description 1
- FLHJIAFUWHPJRT-UHFFFAOYSA-N 2,3,3-trimethylindole Chemical compound C1=CC=C2C(C)(C)C(C)=NC2=C1 FLHJIAFUWHPJRT-UHFFFAOYSA-N 0.000 description 1
- KTADTTCBDAMZIR-UHFFFAOYSA-N 2-(2-hydroxypropoxy)propan-1-ol;hydrate Chemical compound O.CC(O)COC(C)CO KTADTTCBDAMZIR-UHFFFAOYSA-N 0.000 description 1
- JBCUKQQIWSWEOK-UHFFFAOYSA-N 2-(benzenesulfonyl)aniline Chemical compound NC1=CC=CC=C1S(=O)(=O)C1=CC=CC=C1 JBCUKQQIWSWEOK-UHFFFAOYSA-N 0.000 description 1
- LJDSTRZHPWMDPG-UHFFFAOYSA-N 2-(butylamino)ethanol Chemical compound CCCCNCCO LJDSTRZHPWMDPG-UHFFFAOYSA-N 0.000 description 1
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- COBPKKZHLDDMTB-UHFFFAOYSA-N 2-[2-(2-butoxyethoxy)ethoxy]ethanol Chemical compound CCCCOCCOCCOCCO COBPKKZHLDDMTB-UHFFFAOYSA-N 0.000 description 1
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- 235000014113 dietary fatty acids Nutrition 0.000 description 1
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
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- YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 description 1
- XOOMNEFVDUTJPP-UHFFFAOYSA-N naphthalene-1,3-diol Chemical compound C1=CC=CC2=CC(O)=CC(O)=C21 XOOMNEFVDUTJPP-UHFFFAOYSA-N 0.000 description 1
- JRNGUTKWMSBIBF-UHFFFAOYSA-N naphthalene-2,3-diol Chemical compound C1=CC=C2C=C(O)C(O)=CC2=C1 JRNGUTKWMSBIBF-UHFFFAOYSA-N 0.000 description 1
- MNZMMCVIXORAQL-UHFFFAOYSA-N naphthalene-2,6-diol Chemical compound C1=C(O)C=CC2=CC(O)=CC=C21 MNZMMCVIXORAQL-UHFFFAOYSA-N 0.000 description 1
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 229910052700 potassium Inorganic materials 0.000 description 1
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- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
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- MSZHEEJTTAUDJC-UHFFFAOYSA-M sodium 7-acetamido-3-[(4-acetamidophenyl)diazenyl]-4-hydroxynaphthalene-2-sulfonate Chemical compound [Na+].CC(=O)Nc1ccc(cc1)N=Nc1c(O)c2ccc(NC(C)=O)cc2cc1S([O-])(=O)=O MSZHEEJTTAUDJC-UHFFFAOYSA-M 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000012192 staining solution Substances 0.000 description 1
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- 150000003460 sulfonic acids Chemical class 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- FUSRXDHHILMBIG-UHFFFAOYSA-J tetrasodium 7-hydroxy-8-[(4-sulfonatonaphthalen-1-yl)diazenyl]naphthalene-1,3,6-trisulfonate Chemical compound C1=CC=C2C(=C1)C(=CC=C2S(=O)(=O)[O-])N=NC3=C(C(=CC4=CC(=CC(=C43)S(=O)(=O)[O-])S(=O)(=O)[O-])S(=O)(=O)O)[O-].[Na+].[Na+].[Na+].[Na+] FUSRXDHHILMBIG-UHFFFAOYSA-J 0.000 description 1
- UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 description 1
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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
- C09B41/00—Special methods of performing the coupling reaction
- C09B41/001—Special methods of performing the coupling reaction characterised by the coupling medium
- C09B41/002—Special methods of performing the coupling reaction characterised by the coupling medium containing a solvent
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C203/00—Esters of nitric or nitrous acid
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Coloring (AREA)
- Paper (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702049620 DE2049620C3 (de) | 1970-10-09 | 1970-10-09 | Stabile, konzentrierte, saure Stammlösungen von anionischen Farbstoffen, Verfahren zu ihrer Herstellung und ihre Verwendung |
| CH1378771A CH591548A5 (enExample) | 1970-10-09 | 1971-09-21 | |
| GB4666971A GB1356121A (en) | 1970-10-09 | 1971-10-07 | Stock solutions of anionic cyes and their production |
| NL7113867A NL7113867A (enExample) | 1970-10-09 | 1971-10-08 | |
| NL7113871A NL7113871A (en) | 1970-10-09 | 1971-10-08 | Alkylene glycol nitrates - for amine diazotisation by reacting glycol with nitrous acid or nitrogen oxide |
| IT5334771A IT939517B (it) | 1970-10-09 | 1971-10-08 | Soluzioni madri acide stabili concentrate di coloranti anio nici e procedimento per la lo ro produzione |
| BE773659A BE773659A (fr) | 1970-10-09 | 1971-10-08 | Solutions-meres acides, stables et concentrees de colorants anioniques et procede pour leur preparation |
| JP7881371A JPS553382B1 (enExample) | 1970-10-09 | 1971-10-08 | |
| FR7136291A FR2110324B1 (enExample) | 1970-10-09 | 1971-10-08 | |
| FR7234668A FR2155473A5 (enExample) | 1970-10-09 | 1972-09-29 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702049620 DE2049620C3 (de) | 1970-10-09 | 1970-10-09 | Stabile, konzentrierte, saure Stammlösungen von anionischen Farbstoffen, Verfahren zu ihrer Herstellung und ihre Verwendung |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2049620A1 DE2049620A1 (de) | 1972-04-13 |
| DE2049620B2 DE2049620B2 (de) | 1974-09-05 |
| DE2049620C3 true DE2049620C3 (de) | 1975-04-30 |
Family
ID=5784619
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702049620 Expired DE2049620C3 (de) | 1970-10-09 | 1970-10-09 | Stabile, konzentrierte, saure Stammlösungen von anionischen Farbstoffen, Verfahren zu ihrer Herstellung und ihre Verwendung |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS553382B1 (enExample) |
| BE (1) | BE773659A (enExample) |
| CH (1) | CH591548A5 (enExample) |
| DE (1) | DE2049620C3 (enExample) |
| FR (2) | FR2110324B1 (enExample) |
| GB (1) | GB1356121A (enExample) |
| IT (1) | IT939517B (enExample) |
| NL (1) | NL7113867A (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2484431A1 (fr) * | 1980-06-13 | 1981-12-18 | Ugine Kuhlmann | Procede pour la preparation de solutions concentrees de colorants azoiques et solutions ainsi obtenues |
| DE3030918A1 (de) * | 1980-08-16 | 1982-04-01 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von loesungen kationischer azofarbstoffe |
| JPS59199765A (ja) * | 1983-04-27 | 1984-11-12 | Canon Inc | 染料精製装置 |
| DE3417411A1 (de) * | 1983-06-30 | 1985-01-03 | Canon K.K., Tokio/Tokyo | Tintenherstellungssystem |
| US4802989A (en) * | 1983-07-28 | 1989-02-07 | Canon Kabushiki Kaisha | System for purifying dye |
| JPS61113669A (ja) * | 1984-11-08 | 1986-05-31 | Mitsubishi Chem Ind Ltd | 液組成物およびインクジェット記録方法 |
| US4732613A (en) * | 1984-11-08 | 1988-03-22 | Canon Kabushiki Kaisha | Recording liquid |
| DE4137851A1 (de) * | 1991-11-16 | 1993-05-19 | Basf Ag | Verfahren zum faerben von holzfurnieren |
| US6660048B2 (en) | 1995-12-22 | 2003-12-09 | Ciba Specialty Chemicals Corporation | Aqueous dye solutions |
| ATE226973T1 (de) * | 1995-12-22 | 2002-11-15 | Ciba Sc Holding Ag | Wässrige farbstofflösungen |
| DE19621840A1 (de) * | 1996-05-31 | 1997-12-04 | Basf Ag | Verfahren zur Herstellung von Phenylazonaphthalinen |
| CN118562311B (zh) * | 2024-05-16 | 2025-11-11 | 青岛理工大学 | 一种含硝基偶氮型酸致变色酸性染料及其制备方法和应用 |
-
1970
- 1970-10-09 DE DE19702049620 patent/DE2049620C3/de not_active Expired
-
1971
- 1971-09-21 CH CH1378771A patent/CH591548A5/xx not_active IP Right Cessation
- 1971-10-07 GB GB4666971A patent/GB1356121A/en not_active Expired
- 1971-10-08 NL NL7113867A patent/NL7113867A/xx unknown
- 1971-10-08 BE BE773659A patent/BE773659A/xx unknown
- 1971-10-08 FR FR7136291A patent/FR2110324B1/fr not_active Expired
- 1971-10-08 IT IT5334771A patent/IT939517B/it active
- 1971-10-08 JP JP7881371A patent/JPS553382B1/ja active Pending
-
1972
- 1972-09-29 FR FR7234668A patent/FR2155473A5/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS553382B1 (enExample) | 1980-01-24 |
| GB1356121A (en) | 1974-06-12 |
| NL7113867A (enExample) | 1972-04-11 |
| FR2110324B1 (enExample) | 1973-08-10 |
| FR2155473A5 (enExample) | 1973-05-18 |
| DE2049620B2 (de) | 1974-09-05 |
| IT939517B (it) | 1973-02-10 |
| FR2110324A1 (enExample) | 1972-06-02 |
| BE773659A (fr) | 1972-04-10 |
| DE2049620A1 (de) | 1972-04-13 |
| CH591548A5 (enExample) | 1977-09-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8330 | Complete disclaimer |