DE2034543C3 - Sulfonsäuregruppenhaltige Disazofarbstoffe und ein Verfahren zum Färben und Bedrucken von natürlichen und synthetischen Polyamidfasermaterialien unter Verwendung dieser Farbstoffe - Google Patents
Sulfonsäuregruppenhaltige Disazofarbstoffe und ein Verfahren zum Färben und Bedrucken von natürlichen und synthetischen Polyamidfasermaterialien unter Verwendung dieser FarbstoffeInfo
- Publication number
- DE2034543C3 DE2034543C3 DE19702034543 DE2034543A DE2034543C3 DE 2034543 C3 DE2034543 C3 DE 2034543C3 DE 19702034543 DE19702034543 DE 19702034543 DE 2034543 A DE2034543 A DE 2034543A DE 2034543 C3 DE2034543 C3 DE 2034543C3
- Authority
- DE
- Germany
- Prior art keywords
- amino
- sulfonic acid
- azobenzene
- carbon atoms
- dyes
- 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 21
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title claims description 5
- 125000000542 sulfonic acid group Chemical group 0.000 title claims description 3
- 239000004952 Polyamide Substances 0.000 title description 8
- 229920002647 polyamide Polymers 0.000 title description 8
- 238000004043 dyeing Methods 0.000 title description 7
- 239000002657 fibrous material Substances 0.000 title description 4
- 238000000034 method Methods 0.000 title description 4
- -1 phenyl radicals Chemical class 0.000 claims description 27
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000005521 carbonamide group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000000565 sulfonamide group Chemical group 0.000 claims description 2
- 125000002130 sulfonic acid ester group Chemical group 0.000 claims description 2
- 125000003262 carboxylic acid ester group Chemical class [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 claims 1
- 206010039587 Scarlet Fever Diseases 0.000 description 13
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 230000008878 coupling Effects 0.000 description 6
- 238000010168 coupling process Methods 0.000 description 6
- 238000005859 coupling reaction Methods 0.000 description 6
- 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 5
- 239000002253 acid Substances 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- FOINSAWEWXUXPQ-UHFFFAOYSA-N 4-acetamido-2-aminobenzenesulfonic acid Chemical compound CC(=O)NC1=CC=C(S(O)(=O)=O)C(N)=C1 FOINSAWEWXUXPQ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- SJJFBRHJJLGFBJ-UHFFFAOYSA-N CCN(CC)N(C(C)=O)C(C=C1)=CC=C1S(O)(=O)=O Chemical compound CCN(CC)N(C(C)=O)C(C=C1)=CC=C1S(O)(=O)=O SJJFBRHJJLGFBJ-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002168 alkylating agent Substances 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 229940092714 benzenesulfonic acid Drugs 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- SPVAQUCGELAFGL-UHFFFAOYSA-N 3-methoxy-4-phenyldiazenylaniline Chemical compound COC1=CC(N)=CC=C1N=NC1=CC=CC=C1 SPVAQUCGELAFGL-UHFFFAOYSA-N 0.000 description 2
- IWATUKHBZVPRPV-UHFFFAOYSA-N 3-methyl-4-phenyldiazenylaniline Chemical compound CC1=CC(N)=CC=C1N=NC1=CC=CC=C1 IWATUKHBZVPRPV-UHFFFAOYSA-N 0.000 description 2
- KNRCFYFPEMWZPT-UHFFFAOYSA-N 4-[(2-chlorophenyl)diazenyl]aniline Chemical compound C1=CC(N)=CC=C1N=NC1=CC=CC=C1Cl KNRCFYFPEMWZPT-UHFFFAOYSA-N 0.000 description 2
- ZLPGRYNWNGGMFD-UHFFFAOYSA-N 4-[(4-chlorophenyl)diazenyl]aniline Chemical compound C1=CC(N)=CC=C1N=NC1=CC=C(Cl)C=C1 ZLPGRYNWNGGMFD-UHFFFAOYSA-N 0.000 description 2
- YJPKSWNLIDWGNJ-UHFFFAOYSA-N 4-[[4-(trifluoromethyl)phenyl]diazenyl]aniline Chemical compound C1=CC(N)=CC=C1N=NC1=CC=C(C(F)(F)F)C=C1 YJPKSWNLIDWGNJ-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000000370 acceptor Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 229940100198 alkylating agent Drugs 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-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
- 238000009835 boiling Methods 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
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- NYPVTJHUOFXXPS-UHFFFAOYSA-N 2-amino-4-(phenylcarbamoylamino)benzenesulfonic acid Chemical compound C1=C(S(O)(=O)=O)C(N)=CC(NC(=O)NC=2C=CC=CC=2)=C1 NYPVTJHUOFXXPS-UHFFFAOYSA-N 0.000 description 1
- DNNMQDBFXHKNNI-UHFFFAOYSA-N 2-amino-4-(propanoylamino)benzenesulfonic acid Chemical compound CCC(=O)NC1=CC=C(S(O)(=O)=O)C(N)=C1 DNNMQDBFXHKNNI-UHFFFAOYSA-N 0.000 description 1
- BYMZHAPPSICVQH-UHFFFAOYSA-N 2-amino-4-hydroxybenzenesulfonic acid Chemical compound NC1=CC(O)=CC=C1S(O)(=O)=O BYMZHAPPSICVQH-UHFFFAOYSA-N 0.000 description 1
- BDCJBCKISOZMBR-UHFFFAOYSA-N 2-amino-4-methoxybenzenesulfonic acid Chemical compound COC1=CC=C(S(O)(=O)=O)C(N)=C1 BDCJBCKISOZMBR-UHFFFAOYSA-N 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- GLKGYLZTVTWNHB-UHFFFAOYSA-N 2-ethoxy-5-methyl-4-phenyldiazenylaniline Chemical compound C1=C(N)C(OCC)=CC(N=NC=2C=CC=CC=2)=C1C GLKGYLZTVTWNHB-UHFFFAOYSA-N 0.000 description 1
- SSAPXTJFXPHZTE-UHFFFAOYSA-N 2-methoxy-5-methyl-4-[(3-methylphenyl)diazenyl]aniline Chemical compound C1=C(N)C(OC)=CC(N=NC=2C=C(C)C=CC=2)=C1C SSAPXTJFXPHZTE-UHFFFAOYSA-N 0.000 description 1
- SZNYTNIULZADHD-UHFFFAOYSA-N 2-methoxy-5-methyl-4-phenyldiazenylaniline Chemical compound C1=C(N)C(OC)=CC(N=NC=2C=CC=CC=2)=C1C SZNYTNIULZADHD-UHFFFAOYSA-N 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 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
- TUOGLTOIBJYIAO-UHFFFAOYSA-N 3-methyl-4-[(4-methylphenyl)diazenyl]aniline Chemical compound C1=CC(C)=CC=C1N=NC1=CC=C(N)C=C1C TUOGLTOIBJYIAO-UHFFFAOYSA-N 0.000 description 1
- VDUXKWBSXPCZPG-UHFFFAOYSA-N 4-[(2-methylphenyl)diazenyl]aniline Chemical compound CC1=CC=CC=C1N=NC1=CC=C(N)C=C1 VDUXKWBSXPCZPG-UHFFFAOYSA-N 0.000 description 1
- QFCNQNXUCCCOIA-UHFFFAOYSA-N 4-[(3,4-dichlorophenyl)diazenyl]aniline Chemical compound C1=CC(N)=CC=C1N=NC1=CC=C(Cl)C(Cl)=C1 QFCNQNXUCCCOIA-UHFFFAOYSA-N 0.000 description 1
- KCOITMFSLVDOGO-UHFFFAOYSA-N 4-[(3-methylphenyl)diazenyl]aniline Chemical compound CC1=CC=CC(N=NC=2C=CC(N)=CC=2)=C1 KCOITMFSLVDOGO-UHFFFAOYSA-N 0.000 description 1
- 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 1
- GBSHBQHYAZHQBQ-UHFFFAOYSA-N 4-[(4-chlorophenyl)diazenyl]-3-methoxyaniline Chemical compound COC1=CC(N)=CC=C1N=NC1=CC=C(Cl)C=C1 GBSHBQHYAZHQBQ-UHFFFAOYSA-N 0.000 description 1
- VOXCBGXOKNLLKT-UHFFFAOYSA-N 4-[(4-chlorophenyl)diazenyl]-3-methylaniline Chemical compound CC1=CC(N)=CC=C1N=NC1=CC=C(Cl)C=C1 VOXCBGXOKNLLKT-UHFFFAOYSA-N 0.000 description 1
- HFRDSEPZRADQPT-UHFFFAOYSA-N 4-[(4-methoxyphenyl)diazenyl]-3-methylaniline Chemical compound C1=CC(OC)=CC=C1N=NC1=CC=C(N)C=C1C HFRDSEPZRADQPT-UHFFFAOYSA-N 0.000 description 1
- GATYOJFWOCQOSJ-UHFFFAOYSA-N 4-[[3-chloro-4-(trifluoromethyl)phenyl]diazenyl]aniline Chemical compound C1=CC(N)=CC=C1N=NC1=CC=C(C(F)(F)F)C(Cl)=C1 GATYOJFWOCQOSJ-UHFFFAOYSA-N 0.000 description 1
- DTPUGISCGOCDQB-UHFFFAOYSA-N 4-[[4-chloro-2-(trifluoromethyl)phenyl]diazenyl]aniline Chemical compound C1=CC(N)=CC=C1N=NC1=CC=C(Cl)C=C1C(F)(F)F DTPUGISCGOCDQB-UHFFFAOYSA-N 0.000 description 1
- RJWBTWIBUIGANW-UHFFFAOYSA-N 4-chlorobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(Cl)C=C1 RJWBTWIBUIGANW-UHFFFAOYSA-N 0.000 description 1
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- YPNIEDDPXQANGL-UHFFFAOYSA-N C(C)N(N(C1=CC=CC=C1)C(C1=CC=CC=C1)=O)CC Chemical compound C(C)N(N(C1=CC=CC=C1)C(C1=CC=CC=C1)=O)CC YPNIEDDPXQANGL-UHFFFAOYSA-N 0.000 description 1
- WJDZPQQZGUATKA-UHFFFAOYSA-N CCN(CC)N(C(C1=CC=CC=C1)=O)C(C=C1)=CC=C1S(O)(=O)=O Chemical compound CCN(CC)N(C(C1=CC=CC=C1)=O)C(C=C1)=CC=C1S(O)(=O)=O WJDZPQQZGUATKA-UHFFFAOYSA-N 0.000 description 1
- IDQFHERMOFNPEA-UHFFFAOYSA-N CCN(CC)N(C(CCl)=O)C1=CC=CC=C1 Chemical compound CCN(CC)N(C(CCl)=O)C1=CC=CC=C1 IDQFHERMOFNPEA-UHFFFAOYSA-N 0.000 description 1
- MHWQVMNUUJWJHM-UHFFFAOYSA-N N',N'-dimethyl-N-phenylpropanehydrazide Chemical compound CN(N(C1=CC=CC=C1)C(CC)=O)C MHWQVMNUUJWJHM-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012435 aralkylating agent Substances 0.000 description 1
- DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical compound C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 description 1
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- ZODPAUSXBLLKBD-UHFFFAOYSA-N chloroethane chloromethylbenzene Chemical compound C(C1=CC=CC=C1)Cl.C(C)Cl ZODPAUSXBLLKBD-UHFFFAOYSA-N 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- AVSOCXWJUCUDHB-UHFFFAOYSA-N diethyl sulfate;dimethyl sulfate Chemical compound COS(=O)(=O)OC.CCOS(=O)(=O)OCC AVSOCXWJUCUDHB-UHFFFAOYSA-N 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- VRZVPALEJCLXPR-UHFFFAOYSA-N ethyl 4-methylbenzenesulfonate Chemical compound CCOS(=O)(=O)C1=CC=C(C)C=C1 VRZVPALEJCLXPR-UHFFFAOYSA-N 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Substances CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- LYQRHAUPWHXODM-UHFFFAOYSA-N n',n'-diethyl-n-phenylacetohydrazide Chemical compound CCN(CC)N(C(C)=O)C1=CC=CC=C1 LYQRHAUPWHXODM-UHFFFAOYSA-N 0.000 description 1
- MVBATJPUMMMRHR-UHFFFAOYSA-N n',n'-dimethyl-n-phenylacetohydrazide Chemical compound CN(C)N(C(C)=O)C1=CC=CC=C1 MVBATJPUMMMRHR-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
- JVKZECUWJDCVDG-UHFFFAOYSA-N n-(5-amino-2-phenyldiazenylphenyl)acetamide Chemical compound CC(=O)NC1=CC(N)=CC=C1N=NC1=CC=CC=C1 JVKZECUWJDCVDG-UHFFFAOYSA-N 0.000 description 1
- CAVOQZFSLPSGKB-UHFFFAOYSA-N n-(dimethylamino)-n-phenylformamide Chemical compound CN(C)N(C=O)C1=CC=CC=C1 CAVOQZFSLPSGKB-UHFFFAOYSA-N 0.000 description 1
- FCHXQYSXENSTFC-UHFFFAOYSA-N n-[5-amino-2-[(4-chlorophenyl)diazenyl]phenyl]acetamide Chemical compound CC(=O)NC1=CC(N)=CC=C1N=NC1=CC=C(Cl)C=C1 FCHXQYSXENSTFC-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- RCTGMCJBQGBLKT-PAMTUDGESA-N scarlet red Chemical compound CC1=CC=CC=C1\N=N\C(C=C1C)=CC=C1\N=N\C1=C(O)C=CC2=CC=CC=C12 RCTGMCJBQGBLKT-PAMTUDGESA-N 0.000 description 1
- 229960005369 scarlet red Drugs 0.000 description 1
- KKJOSHGDFRDDGD-UHFFFAOYSA-M sodium 2-[[4-methyl-3-(phenylsulfamoyl)phenyl]diazenyl]-4-sulfonaphthalen-1-olate Chemical compound [Na+].Cc1ccc(cc1S(=O)(=O)Nc1ccccc1)N=Nc1cc(c2ccccc2c1O)S([O-])(=O)=O KKJOSHGDFRDDGD-UHFFFAOYSA-M 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/11—Preparation of azo dyes from other azo compounds by introducing hydrocarbon radicals or substituted hydrocarbon radicals on primary or secondary amino groups
-
- 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
- C09B31/04—Disazo dyes from a coupling component "C" containing a directive amino group
- C09B31/043—Amino-benzenes
- C09B31/047—Amino-benzenes containing acid groups, e.g. —CO2H, —SO3H, —PO3H2, —OSO3H, —OPO2H2; Salts thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702034543 DE2034543C3 (de) | 1970-07-11 | 1970-07-11 | Sulfonsäuregruppenhaltige Disazofarbstoffe und ein Verfahren zum Färben und Bedrucken von natürlichen und synthetischen Polyamidfasermaterialien unter Verwendung dieser Farbstoffe |
| NL7109457A NL7109457A (enrdf_load_stackoverflow) | 1970-07-11 | 1971-07-08 | |
| BE769816A BE769816A (fr) | 1970-07-11 | 1971-07-09 | Nouveaux colorants disazoiques |
| CH1526474A CH603754A5 (enrdf_load_stackoverflow) | 1970-07-11 | 1971-07-09 | |
| CH1015471D CH1015471A4 (enrdf_load_stackoverflow) | 1970-07-11 | 1971-07-09 | |
| FR7125208A FR2098337B1 (enrdf_load_stackoverflow) | 1970-07-11 | 1971-07-09 | |
| CH1015471A CH558446A (enrdf_load_stackoverflow) | 1970-07-11 | 1971-07-09 | |
| GB3235571A GB1300366A (en) | 1970-07-11 | 1971-07-09 | Disazo dyestuffs |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702034543 DE2034543C3 (de) | 1970-07-11 | 1970-07-11 | Sulfonsäuregruppenhaltige Disazofarbstoffe und ein Verfahren zum Färben und Bedrucken von natürlichen und synthetischen Polyamidfasermaterialien unter Verwendung dieser Farbstoffe |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2034543A1 DE2034543A1 (de) | 1972-01-20 |
| DE2034543B2 DE2034543B2 (de) | 1978-09-21 |
| DE2034543C3 true DE2034543C3 (de) | 1979-05-17 |
Family
ID=5776533
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702034543 Expired DE2034543C3 (de) | 1970-07-11 | 1970-07-11 | Sulfonsäuregruppenhaltige Disazofarbstoffe und ein Verfahren zum Färben und Bedrucken von natürlichen und synthetischen Polyamidfasermaterialien unter Verwendung dieser Farbstoffe |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE769816A (enrdf_load_stackoverflow) |
| CH (3) | CH603754A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2034543C3 (enrdf_load_stackoverflow) |
| FR (1) | FR2098337B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1300366A (enrdf_load_stackoverflow) |
| NL (1) | NL7109457A (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1075628B (it) * | 1977-03-17 | 1985-04-22 | Montedison Spa | Coloranti acidi per fibre poliamidiche |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE238596C (enrdf_load_stackoverflow) * | ||||
| DE1921046C3 (de) * | 1969-04-25 | 1975-07-31 | Bayer Ag, 5090 Leverkusen | Disazofarbstoffe, deren Herstellung und Verwendung |
| DE1930261C3 (de) * | 1969-06-13 | 1979-05-03 | Bayer Ag, 5090 Leverkusen | Disazofarbstoffe und ihre Verwendung zum Färben stickstoffhaltiger Fasermaterialien |
-
1970
- 1970-07-11 DE DE19702034543 patent/DE2034543C3/de not_active Expired
-
1971
- 1971-07-08 NL NL7109457A patent/NL7109457A/xx unknown
- 1971-07-09 CH CH1526474A patent/CH603754A5/xx not_active IP Right Cessation
- 1971-07-09 CH CH1015471D patent/CH1015471A4/xx unknown
- 1971-07-09 GB GB3235571A patent/GB1300366A/en not_active Expired
- 1971-07-09 FR FR7125208A patent/FR2098337B1/fr not_active Expired
- 1971-07-09 BE BE769816A patent/BE769816A/xx unknown
- 1971-07-09 CH CH1015471A patent/CH558446A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1300366A (en) | 1972-12-20 |
| CH558446A (enrdf_load_stackoverflow) | 1975-01-31 |
| BE769816A (fr) | 1971-11-16 |
| FR2098337A1 (enrdf_load_stackoverflow) | 1972-03-10 |
| FR2098337B1 (enrdf_load_stackoverflow) | 1975-07-11 |
| DE2034543A1 (de) | 1972-01-20 |
| CH603754A5 (enrdf_load_stackoverflow) | 1978-08-31 |
| DE2034543B2 (de) | 1978-09-21 |
| NL7109457A (enrdf_load_stackoverflow) | 1972-01-13 |
| CH1015471A4 (enrdf_load_stackoverflow) | 1974-06-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| EHV | Ceased/renunciation |