CS210639B2 - Preparation method of reactive dyes - Google Patents
Preparation method of reactive dyes Download PDFInfo
- Publication number
- CS210639B2 CS210639B2 CS792975A CS297579A CS210639B2 CS 210639 B2 CS210639 B2 CS 210639B2 CS 792975 A CS792975 A CS 792975A CS 297579 A CS297579 A CS 297579A CS 210639 B2 CS210639 B2 CS 210639B2
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- Czechoslovakia
- Prior art keywords
- formula
- hydroxy
- compound
- group
- acid
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- 239000000985 reactive dye Substances 0.000 title claims abstract description 15
- 238000002360 preparation method Methods 0.000 title claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 15
- 239000000460 chlorine Substances 0.000 claims abstract description 9
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 8
- 125000001424 substituent group Chemical group 0.000 claims abstract description 8
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 31
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 239000002243 precursor Substances 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- 239000000975 dye Substances 0.000 abstract description 54
- 229910006069 SO3H Inorganic materials 0.000 abstract description 5
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 abstract description 4
- 229920002678 cellulose Polymers 0.000 abstract description 2
- 239000001913 cellulose Substances 0.000 abstract description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 abstract 1
- 229910004727 OSO3H Inorganic materials 0.000 abstract 1
- 125000001153 fluoro group Chemical group F* 0.000 abstract 1
- 150000002367 halogens Chemical group 0.000 abstract 1
- -1 diphenylamino Chemical group 0.000 description 94
- 239000002253 acid Substances 0.000 description 90
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 22
- 150000004699 copper complex Chemical class 0.000 description 19
- 239000000243 solution Substances 0.000 description 19
- GBKXRWNDORMHSG-UHFFFAOYSA-N 5-chloro-2,4,6-trifluorobenzene-1,3-dicarbonitrile Chemical compound FC1=C(Cl)C(F)=C(C#N)C(F)=C1C#N GBKXRWNDORMHSG-UHFFFAOYSA-N 0.000 description 18
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 150000003839 salts Chemical class 0.000 description 12
- 239000004753 textile Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
- 229920000742 Cotton Polymers 0.000 description 8
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 8
- 229910052802 copper Inorganic materials 0.000 description 8
- 239000010949 copper Substances 0.000 description 8
- 230000008878 coupling Effects 0.000 description 8
- 238000010168 coupling process Methods 0.000 description 8
- 238000005859 coupling reaction Methods 0.000 description 8
- 238000004043 dyeing Methods 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical group [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 6
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 6
- YCYZAKGKWGMBDF-UHFFFAOYSA-N phenazin-5-ium;hydroxide Chemical compound O.C1=CC=CC2=NC3=CC=CC=C3N=C21 YCYZAKGKWGMBDF-UHFFFAOYSA-N 0.000 description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 description 6
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 5
- 239000003086 colorant Substances 0.000 description 5
- 239000000835 fiber Substances 0.000 description 5
- LAQPNDIUHRHNCV-UHFFFAOYSA-N isophthalonitrile Chemical group N#CC1=CC=CC(C#N)=C1 LAQPNDIUHRHNCV-UHFFFAOYSA-N 0.000 description 5
- 125000001624 naphthyl group Chemical group 0.000 description 5
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 5
- LWTFYBZNGZGGRD-UHFFFAOYSA-N 2,4,6-trifluorobenzene-1,3,5-tricarbonitrile Chemical compound FC1=C(C#N)C(F)=C(C#N)C(F)=C1C#N LWTFYBZNGZGGRD-UHFFFAOYSA-N 0.000 description 4
- JVMSQRAXNZPDHF-UHFFFAOYSA-N 2,4-diaminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C(N)=C1 JVMSQRAXNZPDHF-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000004040 coloring Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 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 description 4
- VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 description 4
- BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 4
- 125000000542 sulfonic acid group Chemical group 0.000 description 4
- ZRHUHDUEXWHZMA-UHFFFAOYSA-N 1,4-dihydropyrazol-5-one Chemical compound O=C1CC=NN1 ZRHUHDUEXWHZMA-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000001491 aromatic compounds Chemical class 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 230000000740 bleeding effect Effects 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- VILFVXYKHXVYAB-UHFFFAOYSA-N naphthalene-2,7-disulfonic acid Chemical compound C1=CC(S(O)(=O)=O)=CC2=CC(S(=O)(=O)O)=CC=C21 VILFVXYKHXVYAB-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000000732 arylene group Chemical group 0.000 description 2
- 239000000987 azo dye Substances 0.000 description 2
- DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical compound C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 125000002843 carboxylic acid group Chemical group 0.000 description 2
- ICIDZHMCYAIUIJ-UHFFFAOYSA-N dinaphthalen-1-yldiazene Chemical compound C1=CC=C2C(N=NC=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 ICIDZHMCYAIUIJ-UHFFFAOYSA-N 0.000 description 2
- 238000002845 discoloration Methods 0.000 description 2
- QKZZMPQRCDDRIN-UHFFFAOYSA-L disodium;3-[[4-amino-2-(carbamoylamino)phenyl]diazenyl]-5-sulfonaphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].NC(=O)NC1=CC(N)=CC=C1N=NC1=CC2=C(S([O-])(=O)=O)C=C(S([O-])(=O)=O)C=C2C=C1S(O)(=O)=O QKZZMPQRCDDRIN-UHFFFAOYSA-L 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- YYHJPNVCYHVPJK-UHFFFAOYSA-N naphthalen-1-yl-(2-phenylnaphthalen-1-yl)diazene Chemical class C1=CC=CC=C1C1=CC=C(C=CC=C2)C2=C1N=NC1=CC=CC2=CC=CC=C12 YYHJPNVCYHVPJK-UHFFFAOYSA-N 0.000 description 2
- 150000002790 naphthalenes Chemical class 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 2
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 2
- 239000010979 ruby Substances 0.000 description 2
- 229910001750 ruby Inorganic materials 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 125000001174 sulfone group Chemical group 0.000 description 2
- RYJATPLJVSILLB-UHFFFAOYSA-N 1-nitro-2-(2-phenylethenyl)benzene Chemical compound [O-][N+](=O)C1=CC=CC=C1C=CC1=CC=CC=C1 RYJATPLJVSILLB-UHFFFAOYSA-N 0.000 description 1
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 description 1
- HEAHMJLHQCESBZ-UHFFFAOYSA-N 2,5-diaminobenzenesulfonic acid Chemical compound NC1=CC=C(N)C(S(O)(=O)=O)=C1 HEAHMJLHQCESBZ-UHFFFAOYSA-N 0.000 description 1
- TWIBZFLMFHIUBI-UHFFFAOYSA-N 2-(1-methoxyphenazin-5-ium-5-yl)benzenesulfonic acid;hydroxide Chemical compound [OH-].C12=CC=CC=C2N=C2C(OC)=CC=CC2=[N+]1C1=CC=CC=C1S(O)(=O)=O TWIBZFLMFHIUBI-UHFFFAOYSA-N 0.000 description 1
- NSMMFSKPGXCMOE-UHFFFAOYSA-N 2-[2-(2-sulfophenyl)ethenyl]benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1C=CC1=CC=CC=C1S(O)(=O)=O NSMMFSKPGXCMOE-UHFFFAOYSA-N 0.000 description 1
- RTMGGHRFSPMMFE-UHFFFAOYSA-N 2-[[5-(2-aminoethyl)-6-hydroxy-4-methyl-2-oxo-1H-pyridin-3-yl]diazenyl]naphthalene-1,5-disulfonic acid Chemical compound NCCC=1C(=C(C(NC=1O)=O)N=NC1=C(C2=CC=CC(=C2C=C1)S(=O)(=O)O)S(=O)(=O)O)C RTMGGHRFSPMMFE-UHFFFAOYSA-N 0.000 description 1
- IFKQEKUPBBGZHK-UHFFFAOYSA-N 2-acetamido-6-[[4-(2-aminoacetyl)phenyl]diazenyl]-5-hydroxynaphthalene-1,7-disulfonic acid Chemical compound CC(=O)Nc1ccc2c(O)c(N=Nc3ccc(cc3)C(=O)CN)c(cc2c1S(O)(=O)=O)S(O)(=O)=O IFKQEKUPBBGZHK-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
- XXZDPVOWJBCNQC-UHFFFAOYSA-N 3-[(4-amino-2-methylphenyl)diazenyl]naphthalene-1,5-disulfonic acid Chemical compound CC1=CC(N)=CC=C1N=NC1=CC(S(O)(=O)=O)=C(C=CC=C2S(O)(=O)=O)C2=C1 XXZDPVOWJBCNQC-UHFFFAOYSA-N 0.000 description 1
- VRPRWHHLUQBISU-UHFFFAOYSA-N 3-[[5-(aminomethyl)-1-sulfonaphthalen-2-yl]diazenyl]-5-benzamido-4-hydroxynaphthalene-2,7-disulfonic acid Chemical compound C1=CC=C(C=C1)C(=O)NC2=C3C(=CC(=C2)S(=O)(=O)O)C=C(C(=C3O)N=NC4=C(C5=CC=CC(=C5C=C4)CN)S(=O)(=O)O)S(=O)(=O)O VRPRWHHLUQBISU-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
- NSCKIHJVSORBIM-UHFFFAOYSA-N 4-[[2-(methylamino)acetyl]amino]naphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=C2C(NC(=O)CNC)=CC(S(O)(=O)=O)=CC2=C1 NSCKIHJVSORBIM-UHFFFAOYSA-N 0.000 description 1
- XSOPXFZFWGKLMS-UHFFFAOYSA-N 4-acetamidonaphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=C2C(NC(=O)C)=CC(S(O)(=O)=O)=CC2=C1 XSOPXFZFWGKLMS-UHFFFAOYSA-N 0.000 description 1
- HWAUAPHDMHWNCM-UHFFFAOYSA-N 4-acetamidonaphthalene-2-sulfonic acid Chemical compound C1=CC=C2C(NC(=O)C)=CC(S(O)(=O)=O)=CC2=C1 HWAUAPHDMHWNCM-UHFFFAOYSA-N 0.000 description 1
- WTTCZWSXMOTFAH-UHFFFAOYSA-N 4-amino-3-[(2,5-disulfophenyl)diazenyl]-5-hydroxynaphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC2=CC(S(O)(=O)=O)=CC(O)=C2C(N)=C1N=NC1=CC(S(O)(=O)=O)=CC=C1S(O)(=O)=O WTTCZWSXMOTFAH-UHFFFAOYSA-N 0.000 description 1
- APRRQJCCBSJQOQ-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(N)=CC(S(O)(=O)=O)=CC2=C1 APRRQJCCBSJQOQ-UHFFFAOYSA-N 0.000 description 1
- AFABYZDPBFSKLR-UHFFFAOYSA-N 5-[(6-amino-1-hydroxy-3,5-disulfonaphthalen-2-yl)diazenyl]-2-hydroxybenzoic acid Chemical compound Nc1ccc2c(O)c(N=Nc3ccc(O)c(c3)C(O)=O)c(cc2c1S(O)(=O)=O)S(O)(=O)=O AFABYZDPBFSKLR-UHFFFAOYSA-N 0.000 description 1
- YEZBOLDRJIAVBA-UHFFFAOYSA-N 5-[(8-amino-1-hydroxy-3,6-disulfonaphthalen-2-yl)diazenyl]-2-hydroxybenzoic acid Chemical compound OC1=C2C(N)=CC(S(O)(=O)=O)=CC2=CC(S(O)(=O)=O)=C1N=NC1=CC=C(O)C(C(O)=O)=C1 YEZBOLDRJIAVBA-UHFFFAOYSA-N 0.000 description 1
- GHACHQXBXGEMPQ-UHFFFAOYSA-N 5-acetamido-3-[[5-(aminomethyl)-1-sulfonaphthalen-2-yl]diazenyl]-4-hydroxynaphthalene-2,7-disulfonic acid Chemical compound OC1=C(C(=CC2=CC(=CC(=C12)NC(C)=O)S(=O)(=O)O)S(=O)(=O)O)N=NC1=C(C2=CC=CC(=C2C=C1)CN)S(=O)(=O)O GHACHQXBXGEMPQ-UHFFFAOYSA-N 0.000 description 1
- HAIMEEBRQYGMSM-UHFFFAOYSA-N 5-amino-4-hydroxy-3-[(2-hydroxy-5-sulfophenyl)diazenyl]naphthalene-2,7-disulfonic acid Chemical compound OC1=C2C(N)=CC(S(O)(=O)=O)=CC2=CC(S(O)(=O)=O)=C1N=NC1=CC(S(O)(=O)=O)=CC=C1O HAIMEEBRQYGMSM-UHFFFAOYSA-N 0.000 description 1
- UDCKXEFJOHLCKM-UHFFFAOYSA-N 5-amino-4-hydroxy-3-phenyldiazenylnaphthalene-2,7-disulfonic acid Chemical compound OC1=C2C(N)=CC(S(O)(=O)=O)=CC2=CC(S(O)(=O)=O)=C1N=NC1=CC=CC=C1 UDCKXEFJOHLCKM-UHFFFAOYSA-N 0.000 description 1
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 description 1
- ZHOVALSFPCDZLE-UHFFFAOYSA-N 5-chlorobenzene-1,3-dicarbonitrile Chemical compound ClC1=CC(C#N)=CC(C#N)=C1 ZHOVALSFPCDZLE-UHFFFAOYSA-N 0.000 description 1
- HBZVNWNSRNTWPS-UHFFFAOYSA-N 6-amino-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(O)C2=CC(N)=CC=C21 HBZVNWNSRNTWPS-UHFFFAOYSA-N 0.000 description 1
- KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 description 1
- ZBILXVWKWMKHEA-UHFFFAOYSA-N 7-amino-4-hydroxy-3-[(2-hydroxy-5-sulfophenyl)diazenyl]naphthalene-2-sulfonic acid Chemical compound OS(=O)(=O)C1=CC2=CC(N)=CC=C2C(O)=C1N=NC1=CC(S(O)(=O)=O)=CC=C1O ZBILXVWKWMKHEA-UHFFFAOYSA-N 0.000 description 1
- WJBNEMQYSHMDPS-UHFFFAOYSA-N 7-amino-4-hydroxy-3-[(2-sulfophenyl)diazenyl]naphthalene-2-sulfonic acid Chemical compound OS(=O)(=O)C1=CC2=CC(N)=CC=C2C(O)=C1N=NC1=CC=CC=C1S(O)(=O)=O WJBNEMQYSHMDPS-UHFFFAOYSA-N 0.000 description 1
- ZPRUFNWBYQKDGT-UHFFFAOYSA-N 7-amino-4-hydroxy-3-[(4-methoxy-2-sulfophenyl)diazenyl]naphthalene-2-sulfonic acid Chemical compound OS(=O)(=O)C1=CC(OC)=CC=C1N=NC1=C(O)C2=CC=C(N)C=C2C=C1S(O)(=O)=O ZPRUFNWBYQKDGT-UHFFFAOYSA-N 0.000 description 1
- RZVHIXYEVGDQDX-UHFFFAOYSA-N 9,10-anthraquinone Chemical group C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 206010003645 Atopy Diseases 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- QGXLSXHQRMJHPY-UHFFFAOYSA-N CC(=O)NC1=C(C=CC=C1C#N)C#N Chemical compound CC(=O)NC1=C(C=CC=C1C#N)C#N QGXLSXHQRMJHPY-UHFFFAOYSA-N 0.000 description 1
- JNPVXKCXJQMUBX-UHFFFAOYSA-N CC1=C(S(O)(=O)=O)C(=O)N(CC)C(O)=C1N=NC1=CC(CCN)=C(C)C=C1S(O)(=O)=O Chemical compound CC1=C(S(O)(=O)=O)C(=O)N(CC)C(O)=C1N=NC1=CC(CCN)=C(C)C=C1S(O)(=O)=O JNPVXKCXJQMUBX-UHFFFAOYSA-N 0.000 description 1
- 101100294115 Caenorhabditis elegans nhr-4 gene Chemical group 0.000 description 1
- 229920003043 Cellulose fiber Polymers 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- 239000005749 Copper compound Substances 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- UXVRMMAXEPWTSX-UHFFFAOYSA-N NC=1C=C(C=CC1S(=O)(=O)O)N=NC=1C(=C(C(N(C1O)CCC1=CC=C(C=C1)S(=O)(=O)O)=O)C(=O)N)C Chemical compound NC=1C=C(C=CC1S(=O)(=O)O)N=NC=1C(=C(C(N(C1O)CCC1=CC=C(C=C1)S(=O)(=O)O)=O)C(=O)N)C UXVRMMAXEPWTSX-UHFFFAOYSA-N 0.000 description 1
- OXGCYIPRVFIVBK-UHFFFAOYSA-N NCC(=O)NC=1C=C(C=CC=1)N1N=C(C(C1=O)N=NC1=C(C=CC(=C1)S(=O)(=O)O)S(=O)(=O)O)C Chemical compound NCC(=O)NC=1C=C(C=CC=1)N1N=C(C(C1=O)N=NC1=C(C=CC(=C1)S(=O)(=O)O)S(=O)(=O)O)C OXGCYIPRVFIVBK-UHFFFAOYSA-N 0.000 description 1
- FYHFJCUOSHPWSK-UHFFFAOYSA-N OS(=O)(=O)CC1=C(C#N)C(=O)N(CC)C(O)=C1N=NC1=CC=C(S(O)(=O)=O)C(N)=C1 Chemical compound OS(=O)(=O)CC1=C(C#N)C(=O)N(CC)C(O)=C1N=NC1=CC=C(S(O)(=O)=O)C(N)=C1 FYHFJCUOSHPWSK-UHFFFAOYSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 239000004115 Sodium Silicate Substances 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- 241001584775 Tunga penetrans Species 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-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
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- CEZCCHQBSQPRMU-UHFFFAOYSA-L chembl174821 Chemical compound [Na+].[Na+].COC1=CC(S([O-])(=O)=O)=C(C)C=C1N=NC1=C(O)C=CC2=CC(S([O-])(=O)=O)=CC=C12 CEZCCHQBSQPRMU-UHFFFAOYSA-L 0.000 description 1
- PZTQVMXMKVTIRC-UHFFFAOYSA-L chembl2028348 Chemical compound [Ca+2].[O-]S(=O)(=O)C1=CC(C)=CC=C1N=NC1=C(O)C(C([O-])=O)=CC2=CC=CC=C12 PZTQVMXMKVTIRC-UHFFFAOYSA-L 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 150000001880 copper compounds Chemical class 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 125000005059 halophenyl group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000009940 knitting Methods 0.000 description 1
- 125000002950 monocyclic group Chemical group 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
- ZPBSAMLXSQCSOX-UHFFFAOYSA-N naphthalene-1,3,6-trisulfonic acid Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=CC2=CC(S(=O)(=O)O)=CC=C21 ZPBSAMLXSQCSOX-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 229910052759 nickel Chemical group 0.000 description 1
- 239000001005 nitro dye Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 229920006391 phthalonitrile polymer Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- WLFXSECCHULRRO-UHFFFAOYSA-N pyridine-2,6-diol Chemical compound OC1=CC=CC(O)=N1 WLFXSECCHULRRO-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 206010041232 sneezing Diseases 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical group C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000009941 weaving Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 210000002268 wool Anatomy 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
- C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
- C09B62/78—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring with other reactive groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Optical Filters (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1777878 | 1978-05-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS210639B2 true CS210639B2 (en) | 1982-01-29 |
Family
ID=10101040
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS792975A CS210639B2 (en) | 1978-05-04 | 1979-04-28 | Preparation method of reactive dyes |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4263206A (it) |
| JP (1) | JPS54146828A (it) |
| CH (1) | CH640558A5 (it) |
| CS (1) | CS210639B2 (it) |
| DE (1) | DE2916715A1 (it) |
| ES (2) | ES479880A1 (it) |
| FR (1) | FR2424944A1 (it) |
| IT (1) | IT1112771B (it) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3025572A1 (de) * | 1980-07-05 | 1982-02-11 | Hoechst Ag, 6000 Frankfurt | Wasserloesliche azoverbindungen, verfahren zu ihrer herstellung und ihre verwendung als farbstoffe |
| US4614742A (en) * | 1985-08-29 | 1986-09-30 | S.D.S. Biotech K.K. | Fluorinated isophthalonitrile compound and nonmedical fungicide containing the same |
| US5171852A (en) * | 1987-01-20 | 1992-12-15 | Imperial Chemical Industries Plc | Triphenodioxazine reactive dyes having sulphonate ester groups |
| EP0568876B1 (de) | 1992-05-04 | 1996-08-28 | Bayer Ag | Reaktivfarbstoffe, deren Herstellung und Verwendung |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1304825A (fr) * | 1960-11-02 | 1962-09-28 | Cassella Farwerke Mainkur Ag | Colorants organiques solubles dans l'eau et leur préparation |
| FR1321960A (fr) * | 1962-05-14 | 1963-03-22 | Acna | Colorants réactifs |
| US3301847A (en) * | 1962-05-14 | 1967-01-31 | Acna | Reactive disazo dyestuffs |
| DE1220061B (de) * | 1962-08-10 | 1966-06-30 | Bayer Ag | Verfahren zur Herstellung von wasserunloeslichen Azofarbstoffen |
| US3274173A (en) * | 1963-10-31 | 1966-09-20 | Interchem Corp | Fluoro, nitrobenzyl sulfonyl amide colorants |
| BE794979A (fr) * | 1972-02-05 | 1973-08-06 | Bayer Ag | Colorants azoiques |
| DE2443482A1 (de) * | 1974-09-11 | 1976-03-25 | Bayer Ag | Azofarbstoffe |
| DE2454518A1 (de) * | 1974-11-16 | 1976-05-20 | Bayer Ag | Azofarbstoffe |
-
1979
- 1979-03-12 US US06/019,404 patent/US4263206A/en not_active Expired - Lifetime
- 1979-04-24 ES ES479880A patent/ES479880A1/es not_active Expired
- 1979-04-24 ES ES479881A patent/ES479881A1/es not_active Expired
- 1979-04-25 DE DE19792916715 patent/DE2916715A1/de not_active Withdrawn
- 1979-04-28 CS CS792975A patent/CS210639B2/cs unknown
- 1979-04-30 IT IT7922279A patent/IT1112771B/it active
- 1979-05-02 JP JP5355679A patent/JPS54146828A/ja active Pending
- 1979-05-03 CH CH414579A patent/CH640558A5/de not_active IP Right Cessation
- 1979-05-03 FR FR7911167A patent/FR2424944A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| IT7922279A0 (it) | 1979-04-30 |
| CH640558A5 (de) | 1984-01-13 |
| DE2916715A1 (de) | 1979-11-08 |
| ES479881A1 (es) | 1980-01-01 |
| JPS54146828A (en) | 1979-11-16 |
| FR2424944A1 (fr) | 1979-11-30 |
| US4263206A (en) | 1981-04-21 |
| FR2424944B1 (it) | 1983-06-24 |
| IT1112771B (it) | 1986-01-20 |
| ES479880A1 (es) | 1980-01-01 |
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