JPS602337B2 - 繊維反応性染料およびその製法 - Google Patents
繊維反応性染料およびその製法Info
- Publication number
- JPS602337B2 JPS602337B2 JP3076576A JP3076576A JPS602337B2 JP S602337 B2 JPS602337 B2 JP S602337B2 JP 3076576 A JP3076576 A JP 3076576A JP 3076576 A JP3076576 A JP 3076576A JP S602337 B2 JPS602337 B2 JP S602337B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- group
- represented
- formulas
- amino
- 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 22
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 239000000835 fiber Substances 0.000 title description 6
- 239000000975 dye Substances 0.000 claims description 66
- -1 cycloaliphatic Chemical group 0.000 claims description 48
- 238000000034 method Methods 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 23
- 239000000126 substance Substances 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 14
- 125000002947 alkylene group Chemical group 0.000 claims description 12
- 125000003277 amino group Chemical group 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- VMKJWLXVLHBJNK-UHFFFAOYSA-N cyanuric fluoride Chemical compound FC1=NC(F)=NC(F)=N1 VMKJWLXVLHBJNK-UHFFFAOYSA-N 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 9
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound 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 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 9
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 8
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims description 8
- 125000000732 arylene group Chemical group 0.000 claims description 8
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical group C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims description 7
- 239000007858 starting material Substances 0.000 claims description 7
- 125000005263 alkylenediamine group Chemical group 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 238000004132 cross linking Methods 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 150000004056 anthraquinones Chemical class 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 2
- 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 claims description 2
- BXWKHWCXQWEOBL-UHFFFAOYSA-N 4,6-difluoro-n-phenyl-1,3,5-triazin-2-amine Chemical compound FC1=NC(F)=NC(NC=2C=CC=CC=2)=N1 BXWKHWCXQWEOBL-UHFFFAOYSA-N 0.000 claims 2
- RKDUVPVDHFMLPC-UHFFFAOYSA-N 4,6-difluorotriazine Chemical compound FC1=CC(F)=NN=N1 RKDUVPVDHFMLPC-UHFFFAOYSA-N 0.000 claims 1
- 125000002723 alicyclic group Chemical group 0.000 claims 1
- 239000002253 acid Substances 0.000 description 57
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 239000000243 solution Substances 0.000 description 21
- 150000003839 salts Chemical class 0.000 description 19
- 230000008878 coupling Effects 0.000 description 17
- 238000010168 coupling process Methods 0.000 description 17
- 238000005859 coupling reaction Methods 0.000 description 17
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 16
- 238000004043 dyeing Methods 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 229920000742 Cotton Polymers 0.000 description 11
- 229910000831 Steel Inorganic materials 0.000 description 11
- 239000010959 steel Substances 0.000 description 11
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 9
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 9
- 238000009833 condensation Methods 0.000 description 9
- 230000005494 condensation Effects 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 229910052802 copper Inorganic materials 0.000 description 8
- 239000010949 copper Substances 0.000 description 8
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 8
- 239000011780 sodium chloride Substances 0.000 description 8
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 7
- 239000004744 fabric Substances 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 235000011121 sodium hydroxide Nutrition 0.000 description 7
- 239000003513 alkali Substances 0.000 description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 6
- 229910052804 chromium Inorganic materials 0.000 description 5
- 239000011651 chromium Substances 0.000 description 5
- 125000001624 naphthyl group Chemical group 0.000 description 5
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 125000004442 acylamino group Chemical group 0.000 description 4
- 150000004984 aromatic diamines Chemical class 0.000 description 4
- 125000002619 bicyclic group Chemical group 0.000 description 4
- 239000004202 carbamide Substances 0.000 description 4
- 125000002843 carboxylic acid group Chemical group 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 3
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 3
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000004982 aromatic amines Chemical class 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 230000003301 hydrolyzing effect Effects 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 150000003021 phthalic acid derivatives Chemical class 0.000 description 3
- 150000003142 primary aromatic amines Chemical class 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical group C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 3
- 229940124530 sulfonamide Drugs 0.000 description 3
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 210000002268 wool Anatomy 0.000 description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- 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 2
- VOWZNBNDMFLQGM-UHFFFAOYSA-N 2,5-dimethylaniline Chemical compound CC1=CC=C(C)C(N)=C1 VOWZNBNDMFLQGM-UHFFFAOYSA-N 0.000 description 2
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 2
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 description 2
- XRTJYEIMLZALBD-UHFFFAOYSA-N 4-(6-methyl-1,3-benzothiazol-2-yl)aniline Chemical compound S1C2=CC(C)=CC=C2N=C1C1=CC=C(N)C=C1 XRTJYEIMLZALBD-UHFFFAOYSA-N 0.000 description 2
- PPVRMPPLECDING-UHFFFAOYSA-N 4-[(4-aminophenyl)diazenyl]benzenesulfonic acid Chemical compound C1=CC(N)=CC=C1N=NC1=CC=C(S(O)(=O)=O)C=C1 PPVRMPPLECDING-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229920003043 Cellulose fiber Polymers 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 150000001412 amines Chemical class 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
- 125000006267 biphenyl group Chemical group 0.000 description 2
- 239000000337 buffer salt Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 150000001989 diazonium salts Chemical class 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 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
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 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 2
- GVWISOJSERXQBM-UHFFFAOYSA-N n-methylpropan-1-amine Chemical compound CCCNC GVWISOJSERXQBM-UHFFFAOYSA-N 0.000 description 2
- FDWBUGCBGXWJLC-UHFFFAOYSA-N naphthalen-1-yl(phenyl)diazene Chemical compound C1=CC=CC=C1N=NC1=CC=CC2=CC=CC=C12 FDWBUGCBGXWJLC-UHFFFAOYSA-N 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
- 150000003022 phthalic acids Chemical class 0.000 description 2
- 239000001007 phthalocyanine dye Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000001488 sodium phosphate Substances 0.000 description 2
- 238000010025 steaming Methods 0.000 description 2
- 238000006277 sulfonation reaction Methods 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- 239000001043 yellow dye Substances 0.000 description 2
- ZNXSFVXZQBETRJ-UHFFFAOYSA-N (3-aminophenyl)urea Chemical compound NC(=O)NC1=CC=CC(N)=C1 ZNXSFVXZQBETRJ-UHFFFAOYSA-N 0.000 description 1
- LBOPEICPUZAMFB-UHFFFAOYSA-N (3-methylphenoxy)methanamine Chemical compound CC1=CC=CC(OCN)=C1 LBOPEICPUZAMFB-UHFFFAOYSA-N 0.000 description 1
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 1
- VJDQIBUPTBGINF-UHFFFAOYSA-N 1,3-dioxo-2-benzofuran-5-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=C2C(=O)OC(=O)C2=C1 VJDQIBUPTBGINF-UHFFFAOYSA-N 0.000 description 1
- SENOENRYIMUSNW-UHFFFAOYSA-N 1,4-diaminonaphthalene-2-sulfonic acid Chemical compound C1=CC=C2C(N)=CC(S(O)(=O)=O)=C(N)C2=C1 SENOENRYIMUSNW-UHFFFAOYSA-N 0.000 description 1
- ZRHUHDUEXWHZMA-UHFFFAOYSA-N 1,4-dihydropyrazol-5-one Chemical compound O=C1CC=NN1 ZRHUHDUEXWHZMA-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- ZMZOSHXUTMDVJR-UHFFFAOYSA-N 1-(4-aminoanilino)-9,10-dioxoanthracene-2,3-disulfonic acid Chemical compound NC1=CC=C(NC2=C(C(=CC=3C(C4=CC=CC=C4C(C2=3)=O)=O)S(=O)(=O)O)S(=O)(=O)O)C=C1 ZMZOSHXUTMDVJR-UHFFFAOYSA-N 0.000 description 1
- ZOHPJXCEVYGLJT-UHFFFAOYSA-N 1-amino-4-(3-amino-4-sulfoanilino)-9,10-dioxoanthracene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C(N)=CC(NC=2C=3C(=O)C4=CC=CC=C4C(=O)C=3C(N)=C(C=2)S(O)(=O)=O)=C1 ZOHPJXCEVYGLJT-UHFFFAOYSA-N 0.000 description 1
- CFFIOFFTJMGMJX-UHFFFAOYSA-N 1-amino-4-[4-(methylamino)-3-sulfoanilino]-9,10-dioxoanthracene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C(NC)=CC=C1NC1=CC(S(O)(=O)=O)=C(N)C2=C1C(=O)C1=CC=CC=C1C2=O CFFIOFFTJMGMJX-UHFFFAOYSA-N 0.000 description 1
- FUGFCIVSIDJOPE-UHFFFAOYSA-N 1-amino-9,10-dioxoanthracene-2,3-disulfonic acid Chemical compound S(=O)(=O)(O)C=1C(=CC=2C(C3=CC=CC=C3C(C2C1N)=O)=O)S(=O)(=O)O FUGFCIVSIDJOPE-UHFFFAOYSA-N 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- XJGIDGNLXAJIOA-UHFFFAOYSA-N 2,11,20,29,37,38,39,40-octazanonacyclo[28.6.1.13,10.112,19.121,28.04,9.013,18.022,27.031,36]tetraconta-1(36),2,4,6,8,10(40),11,13,15,17,19,21(38),22,24,26,28,30,32,34-nonadecaen-37-amine Chemical compound Nn1c2nc3nc(nc4[nH]c(nc5nc(nc1c1ccccc21)c1ccccc51)c1ccccc41)c1ccccc31 XJGIDGNLXAJIOA-UHFFFAOYSA-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
- DVXMQZHDVBYYEQ-UHFFFAOYSA-N 2,4,6-triaminopyridine-3-carbonitrile Chemical compound NC1=CC(N)=C(C#N)C(N)=N1 DVXMQZHDVBYYEQ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- AVYGCQXNNJPXSS-UHFFFAOYSA-N 2,5-dichloroaniline Chemical compound NC1=CC(Cl)=CC=C1Cl AVYGCQXNNJPXSS-UHFFFAOYSA-N 0.000 description 1
- NAZDVUBIEPVUKE-UHFFFAOYSA-N 2,5-dimethoxyaniline Chemical compound COC1=CC=C(OC)C(N)=C1 NAZDVUBIEPVUKE-UHFFFAOYSA-N 0.000 description 1
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- MWOUGPLLVVEUMM-UHFFFAOYSA-N n-ethyl-2-methylaniline Chemical compound CCNC1=CC=CC=C1C MWOUGPLLVVEUMM-UHFFFAOYSA-N 0.000 description 1
- VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical compound [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 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 1
- IAAKNVCARVEIFS-UHFFFAOYSA-M sodium;4-hydroxynaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(O)=CC=C(S([O-])(=O)=O)C2=C1 IAAKNVCARVEIFS-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000004071 soot Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 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
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/04—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH357075A CH615450A5 (en) | 1975-03-20 | 1975-03-20 | Process for preparing fibre-reactive dyes |
| CH3570/75 | 1975-03-20 | ||
| CH2778/76 | 1976-03-05 | ||
| CH277876 | 1976-03-05 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS51119033A JPS51119033A (en) | 1976-10-19 |
| JPS602337B2 true JPS602337B2 (ja) | 1985-01-21 |
Family
ID=25691377
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3076576A Expired JPS602337B2 (ja) | 1975-03-20 | 1976-03-19 | 繊維反応性染料およびその製法 |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS602337B2 (cs) |
| BR (1) | BR7601712A (cs) |
| CA (1) | CA1063600A (cs) |
| CS (1) | CS190527B2 (cs) |
| DE (1) | DE2611550C2 (cs) |
| ES (1) | ES446171A1 (cs) |
| GB (1) | GB1529645A (cs) |
| IT (1) | IT1061627B (cs) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20200070424A (ko) | 2017-12-28 | 2020-06-17 | 닛데쓰마이크로메탈가부시키가이샤 | 반도체 장치용 본딩 와이어 |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH617929A5 (cs) * | 1976-10-15 | 1980-06-30 | Ciba Geigy Ag | |
| DE2729240C2 (de) * | 1977-06-29 | 1982-07-29 | Bayer Ag, 5090 Leverkusen | Azo-Reaktivfarbstoffe |
| LU78082A1 (de) * | 1977-09-06 | 1979-05-23 | Ciba Geigy Ag | Farbstoffe,deren herstellung und verwendung |
| DE2800147C2 (de) * | 1978-01-03 | 1982-05-06 | Basf Ag, 6700 Ludwigshafen | Reaktivfarbstoffe |
| DE3043915A1 (de) * | 1979-12-06 | 1981-06-11 | Sandoz-Patent-GmbH, 7850 Lörrach | Halo-triazinyl verbindungen |
| US5395925A (en) * | 1980-10-07 | 1995-03-07 | Sandoz Ltd. | Asymmetric sulfo group-containing disazo compounds containing two 6-halo-1,3,5-triazinyl groups |
| CH656629A5 (de) * | 1981-08-08 | 1986-07-15 | Sandoz Ag | Tetrakisazoverbindungen mit brueckenglied, verfahren zur herstellung und verwendung. |
| CH669305GA3 (cs) * | 1981-12-11 | 1989-03-15 | ||
| DE3370641D1 (en) * | 1982-06-09 | 1987-05-07 | Ciba Geigy Ag | Process for dyeing or printing fibrous textile materials with reactive dyes |
| GB8619914D0 (en) * | 1986-08-15 | 1986-09-24 | Ici Plc | Reactive dyes |
| US5196033A (en) * | 1986-08-15 | 1993-03-23 | Imperial Chemical Industries Plc | BIS-azotriazinyl reactive dyes having an N-alkyl-phenylenediamine link for cellulose textiles |
| EP0302006B1 (de) * | 1987-07-03 | 1992-02-05 | Ciba-Geigy Ag | Reaktivfarbstoffe, Verfahren zu deren Herstellung und deren Verwendung |
| EP0458743A3 (en) * | 1990-05-21 | 1992-10-21 | Ciba-Geigy Ag | Reactive dyestuffs, methods of their preparation and use |
| ES2106070T3 (es) * | 1990-09-25 | 1997-11-01 | Ciba Geigy Ag | Colorantes y mezclas de colorantes reactivos con las fibras y utilizacion de los mismos. |
| ES2106157T3 (es) * | 1991-01-16 | 1997-11-01 | Ciba Geigy Ag | Colorantes reactivos, procedimiento para su fabricacion y su utilizacion. |
| JPH07504949A (ja) * | 1992-03-06 | 1995-06-01 | チバ スペシャルティ ケミカルズ ホールディング インコーポレーテッド | 反応性染料によるセルロース含有繊維材料の染色法 |
| EP0631008B1 (de) * | 1993-05-24 | 1999-08-18 | Ciba SC Holding AG | Verfahren zum Waschen von Drucken oder Färbungen auf cellulosehaltigen Textilmaterialien |
| TW415961B (en) * | 1994-10-14 | 2000-12-21 | Ciba Sc Holding Ag | Fibre-reactive anthraquinone dyes, process for their preparation, and their use |
| TW418240B (en) * | 1995-07-19 | 2001-01-11 | Ciba Sc Holding Ag | Dye mixtures, processes for their preparation and their use |
| EP0832940B1 (de) * | 1996-09-26 | 2001-10-17 | Ciba SC Holding AG | Farbstoffmischungen, Verfahren zu deren Herstellung und deren Verwendung |
| DE59802774D1 (de) * | 1997-02-07 | 2002-02-28 | Ciba Sc Holding Ag | Wässrige Reaktivfarbstoff-Formulierungen sowie Verfahren zum Färben und Bedrucken von textilen Fasermaterialien |
| KR20010108133A (ko) | 1999-02-05 | 2001-12-07 | 에프. 아. 프라저, 에른스트 알테르 (에. 알테르), 한스 페터 비틀린 (하. 페. 비틀린), 피. 랍 보프, 브이. 스펜글러, 페. 아에글러 | 흑색 염색용 잉크 및 이의 용도 |
| US6068667A (en) * | 1999-05-05 | 2000-05-30 | Everlight Usa, Inc. | Mixtures of symmetrical and unsymmetrical red reactive dyes |
| TWI548704B (zh) | 2015-05-08 | 2016-09-11 | 臺灣永光化學工業股份有限公司 | 高固著數位紡織印花墨水組成物 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1283771A (en) * | 1969-01-16 | 1972-08-02 | Ici Ltd | New reactive disazo dyestuffs |
| GB1288079A (cs) * | 1969-07-04 | 1972-09-06 | ||
| BE787122A (fr) * | 1971-08-04 | 1973-02-05 | Ciba Geigy | Composes azoiques, leur preparation et leur utilisation |
| GB1439801A (en) * | 1973-05-10 | 1976-06-16 | Ici Ltd | Reactive azo dyestuffs |
-
1976
- 1976-03-18 ES ES446171A patent/ES446171A1/es not_active Expired
- 1976-03-18 DE DE19762611550 patent/DE2611550C2/de not_active Expired
- 1976-03-18 IT IT4863776A patent/IT1061627B/it active
- 1976-03-19 CS CS180276A patent/CS190527B2/cs unknown
- 1976-03-19 JP JP3076576A patent/JPS602337B2/ja not_active Expired
- 1976-03-19 CA CA248,220A patent/CA1063600A/en not_active Expired
- 1976-03-19 BR BR7601712A patent/BR7601712A/pt unknown
- 1976-03-19 GB GB1127276A patent/GB1529645A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20200070424A (ko) | 2017-12-28 | 2020-06-17 | 닛데쓰마이크로메탈가부시키가이샤 | 반도체 장치용 본딩 와이어 |
Also Published As
| Publication number | Publication date |
|---|---|
| CA1063600A (en) | 1979-10-02 |
| DE2611550C2 (de) | 1987-03-26 |
| GB1529645A (en) | 1978-10-25 |
| CS190527B2 (en) | 1979-05-31 |
| BR7601712A (pt) | 1976-09-21 |
| ES446171A1 (es) | 1977-10-16 |
| IT1061627B (it) | 1983-04-30 |
| DE2611550A1 (de) | 1976-09-30 |
| JPS51119033A (en) | 1976-10-19 |
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