TW454030B - Reactive bis-, tris- or tetrakisazo dyes containing 2,4-diaminobenzene sulfonic acid as the bis-coupling component, their preparation and use - Google Patents
Reactive bis-, tris- or tetrakisazo dyes containing 2,4-diaminobenzene sulfonic acid as the bis-coupling component, their preparation and use Download PDFInfo
- Publication number
- TW454030B TW454030B TW086100314A TW86100314A TW454030B TW 454030 B TW454030 B TW 454030B TW 086100314 A TW086100314 A TW 086100314A TW 86100314 A TW86100314 A TW 86100314A TW 454030 B TW454030 B TW 454030B
- Authority
- TW
- Taiwan
- Prior art keywords
- group
- formula
- sulfo
- brown
- substituted
- Prior art date
Links
- 239000000975 dye Substances 0.000 title claims description 49
- 238000010168 coupling process Methods 0.000 title claims description 8
- 238000005859 coupling reaction Methods 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 6
- JVMSQRAXNZPDHF-UHFFFAOYSA-N 2,4-diaminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C(N)=C1 JVMSQRAXNZPDHF-UHFFFAOYSA-N 0.000 title description 4
- -1 1-pyridinyl Chemical group 0.000 claims abstract description 59
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims abstract description 56
- 238000004043 dyeing Methods 0.000 claims abstract description 43
- 150000001875 compounds Chemical class 0.000 claims abstract description 40
- 238000007639 printing Methods 0.000 claims abstract description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 22
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 20
- 239000000985 reactive dye Substances 0.000 claims abstract description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 17
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 13
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 12
- 239000000835 fiber Substances 0.000 claims abstract description 11
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 10
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 10
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 8
- 150000002367 halogens Chemical class 0.000 claims abstract description 7
- 239000000463 material Substances 0.000 claims abstract description 6
- 125000005184 naphthylamino group Chemical group C1(=CC=CC2=CC=CC=C12)N* 0.000 claims abstract description 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 3
- 229910004727 OSO3H Inorganic materials 0.000 claims abstract 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 2
- 239000000460 chlorine Substances 0.000 claims description 31
- 238000011049 filling Methods 0.000 claims description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 25
- 229920000742 Cotton Polymers 0.000 claims description 23
- 239000004744 fabric Substances 0.000 claims description 21
- 230000002079 cooperative effect Effects 0.000 claims description 19
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 125000003277 amino group Chemical group 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 13
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- 239000007788 liquid Substances 0.000 claims description 10
- 239000002657 fibrous material Substances 0.000 claims description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 8
- 239000011734 sodium Substances 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 229910052708 sodium Inorganic materials 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 6
- 210000002268 wool Anatomy 0.000 claims description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims description 5
- 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 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 4
- 150000001412 amines Chemical group 0.000 claims description 4
- 239000004202 carbamide Substances 0.000 claims description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
- 238000005096 rolling process Methods 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 239000000661 sodium alginate Substances 0.000 claims description 4
- 235000010413 sodium alginate Nutrition 0.000 claims description 4
- 229940005550 sodium alginate Drugs 0.000 claims description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 4
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 4
- 230000008719 thickening Effects 0.000 claims description 4
- 239000002562 thickening agent Substances 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 239000001049 brown dye Substances 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000002757 morpholinyl group Chemical group 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 claims description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 235000010755 mineral Nutrition 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 239000011492 sheep wool Substances 0.000 claims description 2
- 239000007921 spray Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 4
- 239000000987 azo dye Substances 0.000 claims 2
- PCTMTFRHKVHKIS-BMFZQQSSSA-N (1s,3r,4e,6e,8e,10e,12e,14e,16e,18s,19r,20r,21s,25r,27r,30r,31r,33s,35r,37s,38r)-3-[(2r,3s,4s,5s,6r)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-19,25,27,30,31,33,35,37-octahydroxy-18,20,21-trimethyl-23-oxo-22,39-dioxabicyclo[33.3.1]nonatriaconta-4,6,8,10 Chemical compound C1C=C2C[C@@H](OS(O)(=O)=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2.O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 PCTMTFRHKVHKIS-BMFZQQSSSA-N 0.000 claims 1
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical group C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 claims 1
- DJHGAFSJWGLOIV-UHFFFAOYSA-N Arsenic acid Chemical compound O[As](O)(O)=O DJHGAFSJWGLOIV-UHFFFAOYSA-N 0.000 claims 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- 101100087530 Caenorhabditis elegans rom-1 gene Proteins 0.000 claims 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical group NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 1
- 229920003043 Cellulose fiber Polymers 0.000 claims 1
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 claims 1
- 101100305983 Mus musculus Rom1 gene Proteins 0.000 claims 1
- 229910002651 NO3 Inorganic materials 0.000 claims 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims 1
- 241000489455 Sitta europaea Species 0.000 claims 1
- 229940000488 arsenic acid Drugs 0.000 claims 1
- 235000014121 butter Nutrition 0.000 claims 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbamic acid group Chemical group C(N)(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims 1
- 210000005069 ears Anatomy 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 1
- 229910052742 iron Inorganic materials 0.000 claims 1
- 244000005700 microbiome Species 0.000 claims 1
- 125000005650 substituted phenylene group Chemical group 0.000 claims 1
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 2
- 239000000243 solution Substances 0.000 description 34
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 239000002585 base Substances 0.000 description 12
- 125000001424 substituent group Chemical group 0.000 description 12
- 238000006467 substitution reaction Methods 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
- 229910052801 chlorine Inorganic materials 0.000 description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 230000008878 coupling Effects 0.000 description 6
- 239000003599 detergent Substances 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- 239000011737 fluorine Substances 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 4
- 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000004952 Polyamide Substances 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 3
- 238000006193 diazotization reaction Methods 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229920002647 polyamide Polymers 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000000344 soap Substances 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 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
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 2
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 235000015170 shellfish Nutrition 0.000 description 2
- 229960003080 taurine Drugs 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 1
- UGEHFOSBNBEWMP-UHFFFAOYSA-N 2,3-diaminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1N UGEHFOSBNBEWMP-UHFFFAOYSA-N 0.000 description 1
- ONMOULMPIIOVTQ-UHFFFAOYSA-M 3-Nitrobenzene sulphonate Chemical compound [O-][N+](=O)C1=CC=CC(S([O-])(=O)=O)=C1 ONMOULMPIIOVTQ-UHFFFAOYSA-M 0.000 description 1
- 235000017166 Bambusa arundinacea Nutrition 0.000 description 1
- 235000017491 Bambusa tulda Nutrition 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 1
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 1
- 241001070941 Castanea Species 0.000 description 1
- 235000014036 Castanea Nutrition 0.000 description 1
- 229940126657 Compound 17 Drugs 0.000 description 1
- KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Natural products CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 241000219146 Gossypium Species 0.000 description 1
- 240000006240 Linum usitatissimum Species 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 244000082204 Phyllostachys viridis Species 0.000 description 1
- 235000015334 Phyllostachys viridis Nutrition 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000004115 Sodium Silicate Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical class OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- WJEIYVAPNMUNIU-UHFFFAOYSA-N [Na].OC(O)=O Chemical compound [Na].OC(O)=O WJEIYVAPNMUNIU-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- GFFGJBXGBJISGV-UHFFFAOYSA-N adenyl group Chemical group N1=CN=C2N=CNC2=C1N GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000011425 bamboo Substances 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- DMVOXQPQNTYEKQ-UHFFFAOYSA-N biphenyl-4-amine Chemical compound C1=CC(N)=CC=C1C1=CC=CC=C1 DMVOXQPQNTYEKQ-UHFFFAOYSA-N 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000009120 camo Nutrition 0.000 description 1
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 235000005607 chanvre indien Nutrition 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 230000000875 corresponding effect Effects 0.000 description 1
- 210000004268 dentin Anatomy 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- 125000001245 hexylamino group Chemical group [H]N([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000010409 ironing Methods 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000010446 mirabilite 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
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 125000006308 propyl amino group Chemical group 0.000 description 1
- 239000013535 sea water Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 230000035900 sweating Effects 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 1
- 235000019801 trisodium phosphate Nutrition 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 230000001755 vocal effect Effects 0.000 description 1
- 239000000080 wetting agent Substances 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
- C09B62/01—Disazo or polyazo 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
- C09B62/44—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
- C09B62/4401—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 two or more reactive groups at least one of them being directly attached to a heterocyclic system and at least one of them being directly attached to a non-heterocyclic system
- C09B62/4403—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 two or more reactive groups at least one of them being directly attached to a heterocyclic system and at least one of them being directly attached to a non-heterocyclic system the heterocyclic system being a triazine ring
- C09B62/4411—Azo dyes
- C09B62/4415—Disazo or polyazo 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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/18—Preparation of azo dyes from other azo compounds by acylation of hydroxyl group or of mercapto group
- C09B43/24—Preparation of azo dyes from other azo compounds by acylation of hydroxyl group or of mercapto group with formation of —O—SO2—R or —O—SO3H radicals
-
- 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
- C09B62/503—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 the reactive group being an esterified or non-esterified hydroxyalkyl sulfonyl or mercaptoalkyl sulfonyl group, a quaternised or non-quaternised aminoalkyl sulfonyl group, a heterylmercapto alkyl sulfonyl group, a vinyl sulfonyl or a substituted vinyl sulfonyl group, or a thiophene-dioxide group
- C09B62/507—Azo dyes
- C09B62/513—Disazo or polyazo dyes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/02—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using azo dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH15096 | 1996-01-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW454030B true TW454030B (en) | 2001-09-11 |
Family
ID=4180395
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW086100314A TW454030B (en) | 1996-01-19 | 1997-01-14 | Reactive bis-, tris- or tetrakisazo dyes containing 2,4-diaminobenzene sulfonic acid as the bis-coupling component, their preparation and use |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US5817779A (enExample) |
| EP (1) | EP0785237B1 (enExample) |
| JP (1) | JP4171081B2 (enExample) |
| KR (1) | KR100433351B1 (enExample) |
| CN (1) | CN1097076C (enExample) |
| DE (1) | DE59703980D1 (enExample) |
| ES (1) | ES2159826T3 (enExample) |
| ID (1) | ID15914A (enExample) |
| MY (1) | MY117759A (enExample) |
| PT (1) | PT785237E (enExample) |
| SG (1) | SG79212A1 (enExample) |
| TW (1) | TW454030B (enExample) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SG68660A1 (en) * | 1997-04-07 | 1999-11-16 | Ciba Sc Holding Ag | Mixtures of reactive dyes and their use |
| US5989298A (en) * | 1997-04-07 | 1999-11-23 | Ciba Speciality Chemicals Corporation | Mixtures of reactive dyes and their use |
| DE69903599T2 (de) | 1998-07-21 | 2003-06-12 | Dystar Textilfarben Gmbh & Co Deutschland Kg | Marineblaue Mischungen von faserreaktiven Azofarbstoffen |
| ATE316990T1 (de) * | 2001-10-12 | 2006-02-15 | Ciba Sc Holding Ag | Faserreaktive azofarbstoffe, deren herstellung und deren verwendung |
| WO2003040239A1 (en) * | 2001-11-07 | 2003-05-15 | Ciba Specialty Chemicals Holding Inc. | Fibre-reactive dyes, their preparation and their use |
| DE10212771A1 (de) * | 2002-03-22 | 2003-10-02 | Dystar Textilfarben Gmbh & Co | Wasserlösliche Mono- und Disazofarbstoffe |
| CN1918245B (zh) * | 2004-02-13 | 2010-11-03 | 西巴特殊化学品控股有限公司 | 活性染料混合物及其用途 |
| CN1317336C (zh) * | 2004-09-16 | 2007-05-23 | 明德国际仓储贸易(上海)有限公司 | 季铵盐双偶氮反应性染料及其应用 |
| CN1847324A (zh) * | 2005-04-13 | 2006-10-18 | 明德国际仓储贸易(上海)有限公司 | 纤维反应性染料 |
| CH695613A5 (de) * | 2005-06-08 | 2006-07-14 | Bezema Ag | Mischungen von schwermetallfreien faserreaktiven Farbstoffen auf der Basis von Triazo-Verbindungen, deren Herstellung und Verwendung. |
| DE102005047391A1 (de) | 2005-10-05 | 2007-04-12 | Dystar Textilfarben Gmbh & Co. Deutschland Kg | Farbstoffe und Farbstoffmischungen von faserreaktiven Azofarbstoffen, ihre Herstellung und ihre Verwendung |
| DE102006028229A1 (de) * | 2006-06-20 | 2008-01-10 | Dystar Textilfarben Gmbh & Co Deutschland Kg | Farbstoffmischungen von faserreaktiven Azofarbstoffen, ihre Herstellung und ihre Verwendung |
| DE102007005795A1 (de) | 2007-02-06 | 2008-08-07 | Dystar Textilfarben Gmbh & Co. Deutschland Kg | Mischungen von faserreaktiven Azofarbstoffen |
| CN101235216B (zh) * | 2008-01-22 | 2010-07-21 | 天津德凯化工股份有限公司 | 一种橙色活性染料及其制备方法 |
| US8349029B2 (en) | 2008-12-09 | 2013-01-08 | Dystar Colours Deutschland Gmbh | Fiber-reactive azo dyes and dye mixtures, preparation thereof and use thereof |
| DE102008054404A1 (de) | 2008-12-09 | 2010-06-10 | Dystar Textilfarben Gmbh & Co. Deutschland Kg | Faserreaktive Azofarbstoffe und Farbstoffmischungen, Verfahren zu ihrer Herstellung und ihre Verwendung |
| CN103703083A (zh) | 2011-08-04 | 2014-04-02 | 亨斯迈先进材料(瑞士)有限公司 | 活性染料的混合物及其用途 |
| CN102329522B (zh) * | 2011-09-29 | 2016-08-03 | 天津德凯化工股份有限公司 | 一种活性染料及其制备方法 |
| KR101965472B1 (ko) * | 2012-06-18 | 2019-04-03 | 다이스타 컬러스 디스트리뷰션 게엠베하 | 무금속 반응성 염료, 그의 제조 방법 및 그의 용도 |
| CN104119692A (zh) * | 2013-04-28 | 2014-10-29 | 浙江科永化工有限公司 | 一种活性橙染料化合物及其应用 |
| CN104119693A (zh) * | 2013-04-28 | 2014-10-29 | 浙江科永化工有限公司 | 一种橙色活性染料化合物及其应用 |
| CN104119694A (zh) * | 2013-04-28 | 2014-10-29 | 浙江科永化工有限公司 | 一种活性橙染料化合物及应用 |
| EP2862902A1 (en) * | 2013-08-29 | 2015-04-22 | DyStar Colours Distribution GmbH | Dye mixtures of metal free reactive dyes, production and use |
| CN105176139B (zh) * | 2015-05-26 | 2020-09-29 | 浙江龙盛集团股份有限公司 | 一种多偶氮棕色活性染料化合物及其制备方法和应用 |
| ES2901929T3 (es) * | 2018-02-16 | 2022-03-24 | Huntsman Adv Mat Switzerland | Procedimiento para la curtición y tinción simultáneas de material fibroso que contiene colágeno |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2032927C3 (de) * | 1970-07-03 | 1979-06-13 | Hoechst Ag, 6000 Frankfurt | Wasserlösliche Metallkomplex-Disazofarbstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zum Färben oder Bedrucken von Wolle, Seide, Leder, Polyamidoder Polyurethanfasern oder nativen oder regenerierten Cellulosefasern |
| KR900004223B1 (ko) * | 1987-06-10 | 1990-06-18 | 이화산업 주식회사 | 반응성 디스아조 염료의 제조방법 |
| KR940002560B1 (ko) * | 1991-04-19 | 1994-03-25 | 주식회사 경인양행 | 반응성 흑색염료 조성물 |
| TW279889B (enExample) * | 1993-10-07 | 1996-07-01 | Ciba Geigy Ag |
-
1997
- 1997-01-06 MY MYPI97000036A patent/MY117759A/en unknown
- 1997-01-10 PT PT97810011T patent/PT785237E/pt unknown
- 1997-01-10 EP EP97810011A patent/EP0785237B1/de not_active Expired - Lifetime
- 1997-01-10 DE DE59703980T patent/DE59703980D1/de not_active Expired - Lifetime
- 1997-01-10 ES ES97810011T patent/ES2159826T3/es not_active Expired - Lifetime
- 1997-01-14 JP JP00436397A patent/JP4171081B2/ja not_active Expired - Fee Related
- 1997-01-14 TW TW086100314A patent/TW454030B/zh not_active IP Right Cessation
- 1997-01-15 US US08/783,183 patent/US5817779A/en not_active Expired - Lifetime
- 1997-01-15 SG SG9700090A patent/SG79212A1/en unknown
- 1997-01-17 ID IDP970130A patent/ID15914A/id unknown
- 1997-01-17 CN CN97102273A patent/CN1097076C/zh not_active Expired - Lifetime
- 1997-01-17 KR KR1019970001207A patent/KR100433351B1/ko not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| JPH09194749A (ja) | 1997-07-29 |
| ID15914A (id) | 1997-08-21 |
| CN1097076C (zh) | 2002-12-25 |
| EP0785237B1 (de) | 2001-07-11 |
| JP4171081B2 (ja) | 2008-10-22 |
| CN1163291A (zh) | 1997-10-29 |
| ES2159826T3 (es) | 2001-10-16 |
| KR100433351B1 (ko) | 2005-09-12 |
| EP0785237A1 (de) | 1997-07-23 |
| PT785237E (pt) | 2001-12-28 |
| MY117759A (en) | 2004-08-30 |
| US5817779A (en) | 1998-10-06 |
| DE59703980D1 (de) | 2001-08-16 |
| KR970059234A (ko) | 1997-08-12 |
| SG79212A1 (en) | 2001-03-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| TW454030B (en) | Reactive bis-, tris- or tetrakisazo dyes containing 2,4-diaminobenzene sulfonic acid as the bis-coupling component, their preparation and use | |
| JPH04252270A (ja) | アゾ染料 | |
| US7439340B2 (en) | Reactive dyes containing an alkylthio-s-triazinyl reactive group | |
| TW466263B (en) | Fiber-reactive black dye mixtures and use thereof for dyeing hydroxy-and/or carboxamido-containing fiber material | |
| JPH073176A (ja) | 繊維−反応性染料、それらの製造方法及び用途 | |
| JPS60173060A (ja) | トリアジン化合物およびそれを用いる繊維材料の染色または捺染法 | |
| JPH05125288A (ja) | 反応性アゾ染料 | |
| CS205140B2 (en) | Process for preparing reactive dyes | |
| TW412575B (en) | Reactive dyes, process for their preparation and the use thereof | |
| JP2001510875A (ja) | ピペラジンを含有する反応性染料 | |
| TW293029B (enExample) | ||
| TW520389B (en) | Orange- and scarlet-colored mixtures of reactive dyes | |
| TW406117B (en) | Fibre-reactive dyes containing two triazinyl radicals which are linked via an aliphatic bridge member | |
| TW418240B (en) | Dye mixtures, processes for their preparation and their use | |
| JPH04227970A (ja) | 反応染料、その製造方法と使用方法 | |
| JP2587178B2 (ja) | 水溶性の繊維反応性染料、その製造方法およびその用途 | |
| US5976197A (en) | Dyeing process and dyes | |
| TW411357B (en) | Reactive azo dyes and their preparation | |
| US4338092A (en) | Disazo compounds having a 4,6,8-trisulfonaphthyl diazo components radical and a 2-amino or substituted amino-4-chloro-1,3,5-triazin-6-yl-amino substituent | |
| TW506993B (en) | Reactive dyes, processes for their preparation and process for dyeing or printing a fibre material | |
| JPH0711158A (ja) | 反応性染料 | |
| JPS5842660A (ja) | 反応染料とその製造方法 | |
| TWI282809B (en) | Fibre reactive azo dyes | |
| CA1111025A (en) | Azo dyes, processes for their production and use thereof | |
| GB2162193A (en) | Reactive disazo dyes with monochlorotriazinyl groups |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| GD4A | Issue of patent certificate for granted invention patent | ||
| MM4A | Annulment or lapse of patent due to non-payment of fees |