DE2232541C3 - Monoazo-Reaktivfarbstoffe und ihre Verwendung zum Färben und Bedrucken hydroxyl- oder amidgruppenhaltiger Textilmaterialien - Google Patents
Monoazo-Reaktivfarbstoffe und ihre Verwendung zum Färben und Bedrucken hydroxyl- oder amidgruppenhaltiger TextilmaterialienInfo
- Publication number
- DE2232541C3 DE2232541C3 DE2232541A DE2232541A DE2232541C3 DE 2232541 C3 DE2232541 C3 DE 2232541C3 DE 2232541 A DE2232541 A DE 2232541A DE 2232541 A DE2232541 A DE 2232541A DE 2232541 C3 DE2232541 C3 DE 2232541C3
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- chloro
- methylsulfonyl
- pyrimidinyl
- pyrimidine
- 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
- 239000000985 reactive dye Substances 0.000 title claims description 4
- 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 claims 3
- 238000004043 dyeing Methods 0.000 title description 13
- 239000000463 material Substances 0.000 title description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 title description 4
- 239000004753 textile Substances 0.000 title description 4
- 125000003368 amide group Chemical group 0.000 title description 3
- 239000002253 acid Substances 0.000 claims description 6
- -1 naphthyl radicals Chemical class 0.000 description 42
- 239000000975 dye Substances 0.000 description 41
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 239000000460 chlorine Substances 0.000 description 12
- 229920000742 Cotton Polymers 0.000 description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 10
- 235000011121 sodium hydroxide Nutrition 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 238000006193 diazotization reaction Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 5
- GVBHCMNXRKOJRH-UHFFFAOYSA-N 2,4,5,6-tetrachloropyrimidine Chemical compound ClC1=NC(Cl)=C(Cl)C(Cl)=N1 GVBHCMNXRKOJRH-UHFFFAOYSA-N 0.000 description 5
- GOYNRDSJTYLXBU-UHFFFAOYSA-N 5-chloro-2,4,6-trifluoropyrimidine Chemical compound FC1=NC(F)=C(Cl)C(F)=N1 GOYNRDSJTYLXBU-UHFFFAOYSA-N 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 5
- KTVWISLTJPDQQX-UHFFFAOYSA-N 2-amino-5-(aminomethyl)naphthalene-1-sulfonic acid Chemical compound NC1=CC=C2C(CN)=CC=CC2=C1S(O)(=O)=O KTVWISLTJPDQQX-UHFFFAOYSA-N 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- MNSGOOCAMMSKGI-UHFFFAOYSA-N N-(hydroxymethyl)phthalimide Chemical compound C1=CC=C2C(=O)N(CO)C(=O)C2=C1 MNSGOOCAMMSKGI-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 230000010933 acylation Effects 0.000 description 4
- 238000005917 acylation reaction Methods 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 229910052801 chlorine Inorganic materials 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
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- UOUBPDZUBVJZOQ-UHFFFAOYSA-N n-(hydroxymethyl)benzamide Chemical compound OCNC(=O)C1=CC=CC=C1 UOUBPDZUBVJZOQ-UHFFFAOYSA-N 0.000 description 4
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 4
- NGCRLFIYVFOUMZ-UHFFFAOYSA-N 2,3-dichloroquinoxaline-6-carbonyl chloride Chemical compound N1=C(Cl)C(Cl)=NC2=CC(C(=O)Cl)=CC=C21 NGCRLFIYVFOUMZ-UHFFFAOYSA-N 0.000 description 3
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 3
- TXNSZCSYBXHETP-UHFFFAOYSA-N 2-chloro-n-(hydroxymethyl)acetamide Chemical compound OCNC(=O)CCl TXNSZCSYBXHETP-UHFFFAOYSA-N 0.000 description 3
- CHSHPICPNSLONM-UHFFFAOYSA-N 2-chloroquinoxaline-6-carboxylic acid Chemical compound N1=C(Cl)C=NC2=CC(C(=O)O)=CC=C21 CHSHPICPNSLONM-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- XMYQHJDBLRZMLW-UHFFFAOYSA-N methanolamine Chemical class NCO XMYQHJDBLRZMLW-UHFFFAOYSA-N 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 150000003252 quinoxalines Chemical class 0.000 description 3
- 238000007127 saponification reaction Methods 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 238000010186 staining Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- YXYCPKOAGWDZKX-UHFFFAOYSA-N 2,4-difluoro-5-(trifluoromethyl)pyrimidine Chemical compound FC1=NC=C(C(F)(F)F)C(F)=N1 YXYCPKOAGWDZKX-UHFFFAOYSA-N 0.000 description 2
- FYTLHYRDGXRYEY-UHFFFAOYSA-N 5-Methyl-3-pyrazolamine Chemical compound CC=1C=C(N)NN=1 FYTLHYRDGXRYEY-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 206010039587 Scarlet Fever Diseases 0.000 description 2
- 150000001408 amides Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 125000005521 carbonamide group Chemical group 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- HYFMZOAPNQAXHU-UHFFFAOYSA-N naphthalene-1,7-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(S(=O)(=O)O)=CC=C21 HYFMZOAPNQAXHU-UHFFFAOYSA-N 0.000 description 2
- 238000006053 organic reaction Methods 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- QQOWHRYOXYEMTL-UHFFFAOYSA-N triazin-4-amine Chemical compound N=C1C=CN=NN1 QQOWHRYOXYEMTL-UHFFFAOYSA-N 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- BYVKICLDZSJHAA-UHFFFAOYSA-N 2,3-dibromoquinoxaline-6-carbonyl bromide Chemical compound N1=C(Br)C(Br)=NC2=CC(C(=O)Br)=CC=C21 BYVKICLDZSJHAA-UHFFFAOYSA-N 0.000 description 1
- ZGQQEHVULTVXQD-UHFFFAOYSA-N 2,3-dichloroquinoxaline-6-carboxylic acid Chemical compound N1=C(Cl)C(Cl)=NC2=CC(C(=O)O)=CC=C21 ZGQQEHVULTVXQD-UHFFFAOYSA-N 0.000 description 1
- FYSHPROTETTWKB-UHFFFAOYSA-N 2,4,5,6-tetrabromopyrimidine Chemical compound BrC1=NC(Br)=C(Br)C(Br)=N1 FYSHPROTETTWKB-UHFFFAOYSA-N 0.000 description 1
- KZMWBUVUQLGBBP-UHFFFAOYSA-N 2,4,5,6-tetrafluoropyrimidine Chemical compound FC1=NC(F)=C(F)C(F)=N1 KZMWBUVUQLGBBP-UHFFFAOYSA-N 0.000 description 1
- BIMGULMREAFXSC-UHFFFAOYSA-N 2,4,5-trifluoro-6-methylpyrimidine Chemical compound CC1=NC(F)=NC(F)=C1F BIMGULMREAFXSC-UHFFFAOYSA-N 0.000 description 1
- VHYBUUMUUNCHCK-UHFFFAOYSA-N 2,4,6-tribromo-1,3,5-triazine Chemical compound BrC1=NC(Br)=NC(Br)=N1 VHYBUUMUUNCHCK-UHFFFAOYSA-N 0.000 description 1
- XJNDXSGINZSFDF-UHFFFAOYSA-N 2,4,6-trichloropyrimidine-5-carbonyl chloride Chemical compound ClC(=O)C1=C(Cl)N=C(Cl)N=C1Cl XJNDXSGINZSFDF-UHFFFAOYSA-N 0.000 description 1
- AZVALKSFVWAVOL-UHFFFAOYSA-N 2,4,6-trifluoro-5-methylpyrimidine Chemical compound CC1=C(F)N=C(F)N=C1F AZVALKSFVWAVOL-UHFFFAOYSA-N 0.000 description 1
- CZHWBISSOIPPNL-UHFFFAOYSA-N 2,4,6-trifluoro-5-methylsulfonylpyrimidine Chemical compound CS(=O)(=O)C1=C(F)N=C(F)N=C1F CZHWBISSOIPPNL-UHFFFAOYSA-N 0.000 description 1
- MLLSXQLOUGEEGV-UHFFFAOYSA-N 2,4,6-trifluoro-5-nitropyrimidine Chemical compound [O-][N+](=O)C1=C(F)N=C(F)N=C1F MLLSXQLOUGEEGV-UHFFFAOYSA-N 0.000 description 1
- JOYWMWSTASJQHZ-UHFFFAOYSA-N 2,4,6-trifluoropyrimidine-5-carbonitrile Chemical compound FC1=NC(F)=C(C#N)C(F)=N1 JOYWMWSTASJQHZ-UHFFFAOYSA-N 0.000 description 1
- VFIWQBCLEGAHDR-UHFFFAOYSA-N 2,4,6-tris(benzenesulfonyl)-1,3,5-triazine Chemical compound N=1C(S(=O)(=O)C=2C=CC=CC=2)=NC(S(=O)(=O)C=2C=CC=CC=2)=NC=1S(=O)(=O)C1=CC=CC=C1 VFIWQBCLEGAHDR-UHFFFAOYSA-N 0.000 description 1
- VAOWDUICNHWGRL-UHFFFAOYSA-N 2,4,6-tris(methylsulfonyl)pyrimidine Chemical compound CS(=O)(=O)C1=CC(S(C)(=O)=O)=NC(S(C)(=O)=O)=N1 VAOWDUICNHWGRL-UHFFFAOYSA-N 0.000 description 1
- MIVVPUZFDSCZJE-UHFFFAOYSA-N 2,4-bis(methylsulfonyl)-1,3,5-triazine Chemical compound CS(=O)(=O)C1=NC=NC(S(C)(=O)=O)=N1 MIVVPUZFDSCZJE-UHFFFAOYSA-N 0.000 description 1
- FNSNECVCDMIFBA-UHFFFAOYSA-N 2,4-bis(methylsulfonyl)-6-phenoxy-1,3,5-triazine Chemical compound CS(=O)(=O)C1=NC(S(=O)(=O)C)=NC(OC=2C=CC=CC=2)=N1 FNSNECVCDMIFBA-UHFFFAOYSA-N 0.000 description 1
- CVXWQOAPKWGRTD-UHFFFAOYSA-N 2,4-bis(methylsulfonyl)pyrimidine-5-sulfonyl chloride Chemical compound CS(=O)(=O)C1=NC=C(S(Cl)(=O)=O)C(S(C)(=O)=O)=N1 CVXWQOAPKWGRTD-UHFFFAOYSA-N 0.000 description 1
- NIAMELKDNLLWRH-UHFFFAOYSA-N 2,4-difluoro-5-methylpyrimidine Chemical compound CC1=CN=C(F)N=C1F NIAMELKDNLLWRH-UHFFFAOYSA-N 0.000 description 1
- GJOGRJUICNPNSV-UHFFFAOYSA-N 2,4-difluoro-5-phenylpyrimidine Chemical compound FC1=NC(F)=NC=C1C1=CC=CC=C1 GJOGRJUICNPNSV-UHFFFAOYSA-N 0.000 description 1
- FKSSZHRRUUZKCM-UHFFFAOYSA-N 2,4-difluoro-6-(trifluoromethyl)pyrimidine Chemical compound FC1=CC(C(F)(F)F)=NC(F)=N1 FKSSZHRRUUZKCM-UHFFFAOYSA-N 0.000 description 1
- YKLOPWRWWFKUBX-UHFFFAOYSA-N 2,4-difluoro-6-methylpyrimidine Chemical compound CC1=CC(F)=NC(F)=N1 YKLOPWRWWFKUBX-UHFFFAOYSA-N 0.000 description 1
- ZCHHTEOFXSGDMW-UHFFFAOYSA-N 2,4-difluoro-6-phenylpyrimidine Chemical compound FC1=NC(F)=CC(C=2C=CC=CC=2)=N1 ZCHHTEOFXSGDMW-UHFFFAOYSA-N 0.000 description 1
- AOSHQVWIJNXEMB-UHFFFAOYSA-N 2,4-difluoropyrimidine-5-carbonitrile Chemical compound FC1=NC=C(C#N)C(F)=N1 AOSHQVWIJNXEMB-UHFFFAOYSA-N 0.000 description 1
- YZRMBOOBRWRVJU-UHFFFAOYSA-N 2,6-bis(methylsulfonyl)pyrimidine-4-carbonyl chloride Chemical compound CS(=O)(=O)C1=CC(C(Cl)=O)=NC(S(C)(=O)=O)=N1 YZRMBOOBRWRVJU-UHFFFAOYSA-N 0.000 description 1
- PLVFHLAXDQSLCL-UHFFFAOYSA-N 2,6-dichloro-1h-triazin-4-amine Chemical compound NC1=NN(Cl)NC(Cl)=C1 PLVFHLAXDQSLCL-UHFFFAOYSA-N 0.000 description 1
- VYLHZPZYNPDQBR-UHFFFAOYSA-N 2,6-dichloro-4-(4-methylphenyl)-1h-triazine-5-thiol Chemical compound C1=CC(C)=CC=C1C1=NN(Cl)NC(Cl)=C1S VYLHZPZYNPDQBR-UHFFFAOYSA-N 0.000 description 1
- AMBBZHXGKGNTMI-UHFFFAOYSA-N 2,6-dichloro-4-ethoxy-1h-triazine Chemical compound CCOC1=NN(Cl)NC(Cl)=C1 AMBBZHXGKGNTMI-UHFFFAOYSA-N 0.000 description 1
- IOXIFBCDVPDGJV-UHFFFAOYSA-N 2,6-dichloro-4-methoxy-1h-triazine Chemical compound COC1=NN(Cl)NC(Cl)=C1 IOXIFBCDVPDGJV-UHFFFAOYSA-N 0.000 description 1
- DLMSWGCJMRVWCD-UHFFFAOYSA-N 2,6-dichloro-4-phenoxy-1h-triazine Chemical compound ClN1NC(Cl)=CC(OC=2C=CC=CC=2)=N1 DLMSWGCJMRVWCD-UHFFFAOYSA-N 0.000 description 1
- BHAFVZAFEVCQGJ-UHFFFAOYSA-N 2,6-dichloro-4-phenylsulfanyl-1h-triazine Chemical compound ClN1NC(Cl)=CC(SC=2C=CC=CC=2)=N1 BHAFVZAFEVCQGJ-UHFFFAOYSA-N 0.000 description 1
- JOHYJBDEGASSCP-UHFFFAOYSA-N 2,6-dichloro-n-ethyl-1h-triazin-4-amine Chemical compound CCNC1=NN(Cl)NC(Cl)=C1 JOHYJBDEGASSCP-UHFFFAOYSA-N 0.000 description 1
- CTSJEGLSMYPRJK-UHFFFAOYSA-N 2,6-dichloro-n-methyl-1h-triazin-4-amine Chemical compound CNC1=NN(Cl)NC(Cl)=C1 CTSJEGLSMYPRJK-UHFFFAOYSA-N 0.000 description 1
- WULMCOUFBKKFQE-UHFFFAOYSA-N 2,6-dichloro-n-phenyl-1h-triazin-4-amine Chemical compound ClN1NC(Cl)=CC(NC=2C=CC=CC=2)=N1 WULMCOUFBKKFQE-UHFFFAOYSA-N 0.000 description 1
- NUYJCMGJLNVOML-UHFFFAOYSA-N 2,6-dichloropyrimidine-4-carbonyl chloride Chemical compound ClC(=O)C1=CC(Cl)=NC(Cl)=N1 NUYJCMGJLNVOML-UHFFFAOYSA-N 0.000 description 1
- WFJGZGDYFGUMCA-UHFFFAOYSA-N 2,6-difluoropyrimidine-4-carbonitrile Chemical compound FC1=CC(C#N)=NC(F)=N1 WFJGZGDYFGUMCA-UHFFFAOYSA-N 0.000 description 1
- IJXOQDQYOMRDSO-UHFFFAOYSA-N 2-(benzenesulfonyl)-4,5-dichloropyrimidine Chemical compound N1=C(Cl)C(Cl)=CN=C1S(=O)(=O)C1=CC=CC=C1 IJXOQDQYOMRDSO-UHFFFAOYSA-N 0.000 description 1
- JKGLRGGCGUQNEX-UHFFFAOYSA-N 2-(chloromethyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCl)C(=O)C2=C1 JKGLRGGCGUQNEX-UHFFFAOYSA-N 0.000 description 1
- FTTQEGRVQCXCSZ-UHFFFAOYSA-N 2-amino-3-methyl-5-[[2-(methylamino)acetyl]amino]naphthalene-1-sulfonic acid Chemical compound NC1=C(C)C=C2C(NC(=O)CNC)=CC=CC2=C1S(O)(=O)=O FTTQEGRVQCXCSZ-UHFFFAOYSA-N 0.000 description 1
- JYUAZYQCKQWDHM-UHFFFAOYSA-N 2-amino-5-(benzamidomethyl)naphthalene-1-sulfonic acid Chemical compound C=1C=CC2=C(S(O)(=O)=O)C(N)=CC=C2C=1CNC(=O)C1=CC=CC=C1 JYUAZYQCKQWDHM-UHFFFAOYSA-N 0.000 description 1
- VADDRXYFHXAKIG-UHFFFAOYSA-N 2-amino-5-[(2-chloroacetyl)amino]-3-methylnaphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(O)(=O)=O)=C(N)C(C)=CC2=C1NC(=O)CCl VADDRXYFHXAKIG-UHFFFAOYSA-N 0.000 description 1
- GWIAAIUASRVOIA-UHFFFAOYSA-N 2-aminonaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(N)=CC=C21 GWIAAIUASRVOIA-UHFFFAOYSA-N 0.000 description 1
- JUYQWJULYXCBAV-UHFFFAOYSA-N 2-chloropyrimidine-5-carbonyl chloride Chemical compound ClC(=O)C1=CN=C(Cl)N=C1 JUYQWJULYXCBAV-UHFFFAOYSA-N 0.000 description 1
- LVSMGNXVKQOJGO-UHFFFAOYSA-N 3-(5-amino-3-methylpyrazol-1-yl)-4-chlorobenzenesulfonic acid Chemical compound N1=C(C)C=C(N)N1C1=CC(S(O)(=O)=O)=CC=C1Cl LVSMGNXVKQOJGO-UHFFFAOYSA-N 0.000 description 1
- USABLKDPCXBPRX-UHFFFAOYSA-N 3-[[4,6-bis(methylsulfonyl)-1,3,5-triazin-2-yl]amino]benzenesulfonic acid Chemical compound CS(=O)(=O)C1=NC(S(=O)(=O)C)=NC(NC=2C=C(C=CC=2)S(O)(=O)=O)=N1 USABLKDPCXBPRX-UHFFFAOYSA-N 0.000 description 1
- QIMCIIVGSIZXFU-UHFFFAOYSA-N 3-chloroquinoxaline-2-carbonyl chloride Chemical compound C1=CC=C2N=C(Cl)C(C(=O)Cl)=NC2=C1 QIMCIIVGSIZXFU-UHFFFAOYSA-N 0.000 description 1
- CGIHHZTTZZMCRK-UHFFFAOYSA-N 3-chloroquinoxaline-6-carbonyl chloride Chemical compound N1=CC(Cl)=NC2=CC(C(=O)Cl)=CC=C21 CGIHHZTTZZMCRK-UHFFFAOYSA-N 0.000 description 1
- USWINTIHFQKJTR-UHFFFAOYSA-N 3-hydroxynaphthalene-2,7-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C=C(S(O)(=O)=O)C(O)=CC2=C1 USWINTIHFQKJTR-UHFFFAOYSA-N 0.000 description 1
- AIRRELHUAAZTTL-UHFFFAOYSA-N 3-nitrobenzenesulfonic acid;sodium Chemical compound [Na].OS(=O)(=O)C1=CC=CC([N+]([O-])=O)=C1 AIRRELHUAAZTTL-UHFFFAOYSA-N 0.000 description 1
- TVFFVYDLWNCZBH-UHFFFAOYSA-N 4,5-dichloro-2-ethylsulfonyl-6-methylpyrimidine Chemical compound CCS(=O)(=O)C1=NC(C)=C(Cl)C(Cl)=N1 TVFFVYDLWNCZBH-UHFFFAOYSA-N 0.000 description 1
- YJPYVNMIARMZEK-UHFFFAOYSA-N 4,5-dichloro-6-(chloromethyl)-2-methylsulfonylpyrimidine Chemical compound CS(=O)(=O)C1=NC(Cl)=C(Cl)C(CCl)=N1 YJPYVNMIARMZEK-UHFFFAOYSA-N 0.000 description 1
- NZXOCWXWWQNPOF-UHFFFAOYSA-N 4,5-dichloro-6-methyl-2-methylsulfonylpyrimidine Chemical compound CC1=NC(S(C)(=O)=O)=NC(Cl)=C1Cl NZXOCWXWWQNPOF-UHFFFAOYSA-N 0.000 description 1
- FBDGJZXFKQZWLX-UHFFFAOYSA-N 4,6-bis(methylsulfonyl)pyrimidine Chemical compound CS(=O)(=O)C1=CC(S(C)(=O)=O)=NC=N1 FBDGJZXFKQZWLX-UHFFFAOYSA-N 0.000 description 1
- DROUVIKCNOHKBA-UHFFFAOYSA-N 4,6-dichloro-2-methylsulfonylpyrimidine Chemical compound CS(=O)(=O)C1=NC(Cl)=CC(Cl)=N1 DROUVIKCNOHKBA-UHFFFAOYSA-N 0.000 description 1
- SLCUSSPKUGKMGA-UHFFFAOYSA-N 4-bromo-2,6-difluoropyrimidine Chemical compound FC1=CC(Br)=NC(F)=N1 SLCUSSPKUGKMGA-UHFFFAOYSA-N 0.000 description 1
- ZRWALVBIVUPROW-UHFFFAOYSA-N 4-chloro-2,6-bis(methylsulfonyl)pyrimidine-5-carbonyl chloride Chemical compound CS(=O)(=O)C1=NC(Cl)=C(C(Cl)=O)C(S(C)(=O)=O)=N1 ZRWALVBIVUPROW-UHFFFAOYSA-N 0.000 description 1
- VJMKIDUNVPFBOB-UHFFFAOYSA-N 4-chloro-2,6-difluoro-5-methylpyrimidine Chemical compound CC1=C(F)N=C(F)N=C1Cl VJMKIDUNVPFBOB-UHFFFAOYSA-N 0.000 description 1
- WOQIMJVYLVUMGO-UHFFFAOYSA-N 4-chloro-2,6-difluoro-5-nitropyrimidine Chemical compound [O-][N+](=O)C1=C(F)N=C(F)N=C1Cl WOQIMJVYLVUMGO-UHFFFAOYSA-N 0.000 description 1
- ACYSJALOFWHUEX-UHFFFAOYSA-N 4-chloro-2,6-difluoropyrimidine Chemical compound FC1=CC(Cl)=NC(F)=N1 ACYSJALOFWHUEX-UHFFFAOYSA-N 0.000 description 1
- POWFLCAWHSPOHP-UHFFFAOYSA-N 4-chloro-2-methylpyrimidine-5-carbonyl chloride Chemical compound CC1=NC=C(C(Cl)=O)C(Cl)=N1 POWFLCAWHSPOHP-UHFFFAOYSA-N 0.000 description 1
- WGNKUINKIVFGBC-UHFFFAOYSA-N 4-chloro-6-methyl-2-methylsulfonyl-5-nitropyrimidine Chemical compound CC1=NC(S(C)(=O)=O)=NC(Cl)=C1[N+]([O-])=O WGNKUINKIVFGBC-UHFFFAOYSA-N 0.000 description 1
- OLOLDTJCNAOMQJ-UHFFFAOYSA-N 4-chloro-6-methyl-2-methylsulfonylpyrimidine Chemical compound CC1=CC(Cl)=NC(S(C)(=O)=O)=N1 OLOLDTJCNAOMQJ-UHFFFAOYSA-N 0.000 description 1
- BYJUMOSWVALFCO-UHFFFAOYSA-N 4-chloro-6-methyl-2-methylsulfonylpyrimidine-5-sulfonyl chloride Chemical compound CC1=NC(S(C)(=O)=O)=NC(Cl)=C1S(Cl)(=O)=O BYJUMOSWVALFCO-UHFFFAOYSA-N 0.000 description 1
- LNJVTFNEAPYZIU-UHFFFAOYSA-N 4-chloro-6-methylsulfonylpyrimidine Chemical compound CS(=O)(=O)C1=CC(Cl)=NC=N1 LNJVTFNEAPYZIU-UHFFFAOYSA-N 0.000 description 1
- SXCSXKQTOUHQIY-UHFFFAOYSA-N 4-hydroxynaphthalene-1,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=C2C(O)=CC=C(S(O)(=O)=O)C2=C1 SXCSXKQTOUHQIY-UHFFFAOYSA-N 0.000 description 1
- LVILGAOSPDLNRM-UHFFFAOYSA-N 4-methylpyrimidine Chemical compound CC1=CC=NC=N1 LVILGAOSPDLNRM-UHFFFAOYSA-N 0.000 description 1
- FRSCGYMSBBDAKE-UHFFFAOYSA-N 5-(chloromethyl)-2,4,6-trifluoropyrimidine Chemical compound FC1=NC(F)=C(CCl)C(F)=N1 FRSCGYMSBBDAKE-UHFFFAOYSA-N 0.000 description 1
- BOLIYMRNXVAWIJ-UHFFFAOYSA-N 5-bromo-2,4,6-trifluoropyrimidine Chemical compound FC1=NC(F)=C(Br)C(F)=N1 BOLIYMRNXVAWIJ-UHFFFAOYSA-N 0.000 description 1
- ZBTCTILYGQNVOJ-UHFFFAOYSA-N 5-bromo-2,4-difluoro-6-methylpyrimidine Chemical compound CC1=NC(F)=NC(F)=C1Br ZBTCTILYGQNVOJ-UHFFFAOYSA-N 0.000 description 1
- XKHYTPKPHOHPIJ-UHFFFAOYSA-N 5-bromo-4-chloro-6-methyl-2-methylsulfonylpyrimidine Chemical compound CC1=NC(S(C)(=O)=O)=NC(Cl)=C1Br XKHYTPKPHOHPIJ-UHFFFAOYSA-N 0.000 description 1
- GNDKYGCYDWCLHH-UHFFFAOYSA-N 5-chloro-2,4-bis(methylsulfonyl)pyrimidine Chemical compound CS(=O)(=O)C1=NC=C(Cl)C(S(C)(=O)=O)=N1 GNDKYGCYDWCLHH-UHFFFAOYSA-N 0.000 description 1
- RMULVUFPLMJWOK-UHFFFAOYSA-N 5-chloro-2,4-difluoro-6-methylpyrimidine Chemical compound CC1=NC(F)=NC(F)=C1Cl RMULVUFPLMJWOK-UHFFFAOYSA-N 0.000 description 1
- XZSZSTCLQANXKU-UHFFFAOYSA-N 5-chloro-2,4-difluoropyrimidine Chemical compound FC1=NC=C(Cl)C(F)=N1 XZSZSTCLQANXKU-UHFFFAOYSA-N 0.000 description 1
- FCMIDLUGAKOJNR-UHFFFAOYSA-N 5-chloro-4-methyl-2,6-bis(methylsulfonyl)pyrimidine Chemical compound CC1=NC(S(C)(=O)=O)=NC(S(C)(=O)=O)=C1Cl FCMIDLUGAKOJNR-UHFFFAOYSA-N 0.000 description 1
- YLKCHWCYYNKADS-UHFFFAOYSA-N 5-hydroxynaphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(O)=CC=CC2=C1S(O)(=O)=O YLKCHWCYYNKADS-UHFFFAOYSA-N 0.000 description 1
- CNNNFDGIKSGUIS-UHFFFAOYSA-N 6-amino-4-benzoyl-5-hydroxynaphthalene-1,7-disulfonic acid Chemical compound C1=CC(S(O)(=O)=O)=C2C=C(S(O)(=O)=O)C(N)=C(O)C2=C1C(=O)C1=CC=CC=C1 CNNNFDGIKSGUIS-UHFFFAOYSA-N 0.000 description 1
- OZDPATQEBXWLPZ-UHFFFAOYSA-N 6-chloro-2-methylsulfonylpyrimidine-4-carboxylic acid Chemical compound CS(=O)(=O)C1=NC(Cl)=CC(C(O)=O)=N1 OZDPATQEBXWLPZ-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- XJKHHGWQULDTQA-UHFFFAOYSA-N ClN1NC(=CC(=N1)Cl)N Chemical compound ClN1NC(=CC(=N1)Cl)N XJKHHGWQULDTQA-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 102100022404 E3 ubiquitin-protein ligase Midline-1 Human genes 0.000 description 1
- 101710102210 E3 ubiquitin-protein ligase Midline-1 Proteins 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 125000001769 aryl amino group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 1
- 239000000987 azo dye Substances 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
- 239000011230 binding agent Substances 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 235000019646 color tone Nutrition 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002996 emotional effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 235000019233 fast yellow AB Nutrition 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical class F* 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-O hydrazinium(1+) Chemical compound [NH3+]N OAKJQQAXSVQMHS-UHFFFAOYSA-O 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- USPGWRYCHDAJCB-UHFFFAOYSA-N methyl 2,4-difluoropyrimidine-5-carboxylate Chemical compound COC(=O)C1=CN=C(F)N=C1F USPGWRYCHDAJCB-UHFFFAOYSA-N 0.000 description 1
- YSEQKGHEMQCJCC-UHFFFAOYSA-N methyl 2,6-difluoropyrimidine-4-carboxylate Chemical compound COC(=O)C1=CC(F)=NC(F)=N1 YSEQKGHEMQCJCC-UHFFFAOYSA-N 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 1
- CIUJQWLLGXKZQD-UHFFFAOYSA-N n-(chloromethyl)benzamide Chemical compound ClCNC(=O)C1=CC=CC=C1 CIUJQWLLGXKZQD-UHFFFAOYSA-N 0.000 description 1
- LDHTUNVLBUNXKK-UHFFFAOYSA-N n-(hydroxymethyl)-n-methylacetamide Chemical compound OCN(C)C(C)=O LDHTUNVLBUNXKK-UHFFFAOYSA-N 0.000 description 1
- HWJHZLJIIWOTGZ-UHFFFAOYSA-N n-(hydroxymethyl)acetamide Chemical compound CC(=O)NCO HWJHZLJIIWOTGZ-UHFFFAOYSA-N 0.000 description 1
- HLGWPTPAYKLATN-UHFFFAOYSA-N n-(methoxymethyl)benzamide Chemical compound COCNC(=O)C1=CC=CC=C1 HLGWPTPAYKLATN-UHFFFAOYSA-N 0.000 description 1
- DIEOESIZLAHURK-UHFFFAOYSA-N n-naphthalen-2-ylacetamide Chemical compound C1=CC=CC2=CC(NC(=O)C)=CC=C21 DIEOESIZLAHURK-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 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
- 230000020477 pH reduction Effects 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000001557 phthalyl group Chemical group C(=O)(O)C1=C(C(=O)*)C=CC=C1 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920006306 polyurethane fiber Polymers 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000004580 weight loss Effects 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/002—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the linkage of the reactive group being alternatively specified
- C09B62/006—Azodyes
- C09B62/008—Monoazo 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/002—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the linkage of the reactive group being alternatively specified
- C09B62/006—Azodyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (19)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2232541A DE2232541C3 (de) | 1972-07-03 | 1972-07-03 | Monoazo-Reaktivfarbstoffe und ihre Verwendung zum Färben und Bedrucken hydroxyl- oder amidgruppenhaltiger Textilmaterialien |
| IT26026/73A IT990815B (it) | 1972-07-03 | 1973-06-28 | Coloranti azoici reattivi |
| CH953973D CH953973A4 (enExample) | 1972-07-03 | 1973-06-29 | |
| BE132901A BE801661A (fr) | 1972-07-03 | 1973-06-29 | Colorants azoiques reactifs |
| JP7300973A JPS5543025B2 (enExample) | 1972-07-03 | 1973-06-29 | |
| CA175,278A CA994330A (en) | 1972-07-03 | 1973-06-29 | Azo reactive dyestuffs |
| CH1547675A CH582739A5 (enExample) | 1972-07-03 | 1973-06-29 | |
| CH953973A CH572546B5 (enExample) | 1972-07-03 | 1973-06-29 | |
| GB3142073A GB1431322A (en) | 1972-07-03 | 1973-07-02 | Reactive azo dyestuffs |
| NL7309200A NL7309200A (enExample) | 1972-07-03 | 1973-07-02 | |
| ES416498A ES416498A1 (es) | 1972-07-03 | 1973-07-02 | Procedimiento para la obtencion de colorantes azoicos reac-tivos. |
| DD171990A DD107302A5 (enExample) | 1972-07-03 | 1973-07-02 | |
| GB3975975A GB1431323A (en) | 1972-07-03 | 1973-07-02 | Aminonaphthalenesulphonic acids |
| AT584573A AT320100B (de) | 1972-07-03 | 1973-07-03 | Verfahren zur Herstellung von neuen Azoreaktivfarbstoffen |
| US05/376,184 US4126609A (en) | 1972-07-03 | 1973-07-03 | Azo dyestuff with a fiber-reactive group attached to a naphthalene sulphonic acid component |
| FR7324415A FR2236905B1 (enExample) | 1972-07-03 | 1973-07-03 | |
| AT17974A AT334313B (de) | 1972-07-03 | 1974-01-10 | Verfahren zum farben und bedrucken von hydroxyl- oder amidgruppenhaltigen materialien |
| JP51011493A JPS5263488A (en) | 1972-07-03 | 1976-02-06 | Dyeing and printing method |
| US05/656,251 US4049704A (en) | 1972-07-03 | 1976-02-09 | 2-Amino-1-sulfonaphthalene containing acylaminomethyl substituent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2232541A DE2232541C3 (de) | 1972-07-03 | 1972-07-03 | Monoazo-Reaktivfarbstoffe und ihre Verwendung zum Färben und Bedrucken hydroxyl- oder amidgruppenhaltiger Textilmaterialien |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2232541A1 DE2232541A1 (de) | 1974-01-17 |
| DE2232541B2 DE2232541B2 (de) | 1977-10-27 |
| DE2232541C3 true DE2232541C3 (de) | 1978-06-15 |
Family
ID=5849522
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2232541A Expired DE2232541C3 (de) | 1972-07-03 | 1972-07-03 | Monoazo-Reaktivfarbstoffe und ihre Verwendung zum Färben und Bedrucken hydroxyl- oder amidgruppenhaltiger Textilmaterialien |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4126609A (enExample) |
| JP (2) | JPS5543025B2 (enExample) |
| AT (1) | AT320100B (enExample) |
| BE (1) | BE801661A (enExample) |
| CA (1) | CA994330A (enExample) |
| CH (3) | CH572546B5 (enExample) |
| DD (1) | DD107302A5 (enExample) |
| DE (1) | DE2232541C3 (enExample) |
| ES (1) | ES416498A1 (enExample) |
| FR (1) | FR2236905B1 (enExample) |
| GB (2) | GB1431323A (enExample) |
| IT (1) | IT990815B (enExample) |
| NL (1) | NL7309200A (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4299764A (en) | 1978-07-20 | 1981-11-10 | Bayer Aktiengesellschaft | Azo reactive dyestuffs |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2549570C2 (de) * | 1975-11-05 | 1983-05-19 | Bayer Ag, 5090 Leverkusen | Azo-Reaktivfarbstoffe |
| LU77430A1 (enExample) * | 1977-05-27 | 1979-01-19 | ||
| LU78420A1 (de) * | 1977-10-31 | 1979-06-01 | Ciba Geigy Ag | Farbstoffe,deren herstellung und verwendung |
| CH636080A5 (de) * | 1978-04-03 | 1983-05-13 | Ciba Geigy Ag | Farbstoffzwischenprodukte und deren herstellung. |
| DE2825594A1 (de) * | 1978-06-10 | 1979-12-20 | Bayer Ag | Azo-reaktivfarbstoffe |
| DE2829711C2 (de) * | 1978-07-06 | 1986-04-03 | Bayer Ag, 5090 Leverkusen | Azoreaktivfarbstoff |
| DE2903021A1 (de) * | 1979-01-26 | 1980-07-31 | Bayer Ag | Azoreaktivfarbstoffe |
| NO810202L (no) * | 1980-01-29 | 1981-07-30 | Fosroc International Ltd | Kapsel inneholdende sementholdig materiale. |
| DE3025244A1 (de) * | 1980-07-03 | 1982-01-28 | Bayer Ag, 5090 Leverkusen | Dis-azoreaktivfarbstoffe, verfahren zu ihrer herstellung und ihre verwendung zum faerben und bedrucken von stickstoff-und/oder hydroxylgruppenhaltigen materialien |
| DE3048694A1 (de) * | 1980-12-23 | 1982-07-08 | Bayer Ag, 5090 Leverkusen | Naphthalin-derivate, ihre herstellung und ihre verwendung |
| DE3465104D1 (en) * | 1983-07-29 | 1987-09-03 | Ciba Geigy Ag | Reactive dyes, their preparation and their use |
| DE3464626D1 (en) * | 1983-08-30 | 1987-08-13 | Ciba Geigy Ag | Reactive dyes, their preparation and their use |
| DE4100513A1 (de) * | 1991-01-10 | 1992-07-16 | Bayer Ag | Verbessertes verfahren zur herstellung eines substituierten 1-amino-2-sulfonaphthalins |
| DE19525608A1 (de) * | 1995-07-14 | 1997-01-16 | Bayer Ag | Substantive Disazofarbstoffe |
| EP1469039A1 (de) * | 2003-04-17 | 2004-10-20 | Clariant International Ltd. | Faserreaktive Azofarbstoffe |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB837953A (en) * | 1957-08-23 | 1960-06-15 | Ici Ltd | New monoazo triazine dyestuffs |
| CH420414A (de) * | 1959-04-29 | 1966-09-15 | Sandoz Ag | Verfahren zur Herstellung von Pyrimidinfarbstoffen |
| CH370504A (de) * | 1958-10-13 | 1963-07-15 | Ciba Geigy | Verfahren zur Herstellung neuer Monoazofarbstoffe |
| US2951072A (en) * | 1959-02-27 | 1960-08-30 | Ici Ltd | Monoazo dyestuffs of the azo naphthalene series containing a monohalogeno-s-triazinenucleus |
| CH406480A (de) * | 1960-01-29 | 1966-01-31 | Sandoz Ag | Verfahren zur Herstellung von Reaktivfarbstoffen |
| BE618604A (enExample) * | 1960-06-24 | |||
| CH467324A (de) * | 1960-10-06 | 1969-01-15 | Sandoz Ag | Verfahren zur Herstellung von Farbstoffen |
| NL141236B (nl) * | 1961-11-17 | 1974-02-15 | Ciba Geigy | Werkwijze ter bereiding van monoazokleurstoffen, die als koppelingscomponent de rest van een door een halogeentriazinylrest gesubstitueerd naftaleensulfonzuur bevatten, werkwijze voor het verven of bedrukken van meervoudig gehydroxyleerd vezelmateriaal onder toepassing van deze kleurstoffen, alsmede het verkregen gevormde, geverfde of bedrukte materiaal. |
| US3277075A (en) * | 1963-10-21 | 1966-10-04 | Gen Aniline & Film Corp | Dyestuffs containing hydroxyethyl-sulfonylmethyl groups |
| CH472481A (de) * | 1964-12-01 | 1969-05-15 | Ciba Geigy | Verfahren zur Herstellung neuer Azofarbstoffe |
| DE1544528A1 (de) * | 1965-07-15 | 1970-04-02 | Bayer Ag | Azofarbstoffe,deren Metallkomplexverbindungen und Verfahren zu deren Herstellung |
| CH476084A (de) * | 1965-11-16 | 1969-07-31 | Ciba Geigy | Verfahren zur Herstellung neuer Azofarbstoffe |
-
1972
- 1972-07-03 DE DE2232541A patent/DE2232541C3/de not_active Expired
-
1973
- 1973-06-28 IT IT26026/73A patent/IT990815B/it active
- 1973-06-29 CH CH953973A patent/CH572546B5/xx not_active IP Right Cessation
- 1973-06-29 BE BE132901A patent/BE801661A/xx not_active IP Right Cessation
- 1973-06-29 JP JP7300973A patent/JPS5543025B2/ja not_active Expired
- 1973-06-29 CA CA175,278A patent/CA994330A/en not_active Expired
- 1973-06-29 CH CH953973D patent/CH953973A4/xx unknown
- 1973-06-29 CH CH1547675A patent/CH582739A5/xx not_active IP Right Cessation
- 1973-07-02 ES ES416498A patent/ES416498A1/es not_active Expired
- 1973-07-02 NL NL7309200A patent/NL7309200A/xx unknown
- 1973-07-02 DD DD171990A patent/DD107302A5/xx unknown
- 1973-07-02 GB GB3975975A patent/GB1431323A/en not_active Expired
- 1973-07-02 GB GB3142073A patent/GB1431322A/en not_active Expired
- 1973-07-03 AT AT584573A patent/AT320100B/de not_active IP Right Cessation
- 1973-07-03 FR FR7324415A patent/FR2236905B1/fr not_active Expired
- 1973-07-03 US US05/376,184 patent/US4126609A/en not_active Expired - Lifetime
-
1976
- 1976-02-06 JP JP51011493A patent/JPS5263488A/ja active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4299764A (en) | 1978-07-20 | 1981-11-10 | Bayer Aktiengesellschaft | Azo reactive dyestuffs |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5543025B2 (enExample) | 1980-11-04 |
| JPS4952828A (enExample) | 1974-05-22 |
| NL7309200A (enExample) | 1974-01-07 |
| JPS5263488A (en) | 1977-05-25 |
| GB1431323A (en) | 1976-04-07 |
| CH572546B5 (enExample) | 1976-02-13 |
| DE2232541B2 (de) | 1977-10-27 |
| JPS5729592B2 (enExample) | 1982-06-23 |
| FR2236905A1 (enExample) | 1975-02-07 |
| CA994330A (en) | 1976-08-03 |
| CH953973A4 (enExample) | 1975-05-30 |
| CH582739A5 (enExample) | 1976-12-15 |
| AT320100B (de) | 1975-01-27 |
| GB1431322A (en) | 1976-04-07 |
| DE2232541A1 (de) | 1974-01-17 |
| US4126609A (en) | 1978-11-21 |
| FR2236905B1 (enExample) | 1977-02-18 |
| ES416498A1 (es) | 1976-03-01 |
| IT990815B (it) | 1975-07-10 |
| DD107302A5 (enExample) | 1974-07-20 |
| BE801661A (fr) | 1974-01-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) |