JPS6338071B2 - - Google Patents
Info
- Publication number
- JPS6338071B2 JPS6338071B2 JP59225644A JP22564484A JPS6338071B2 JP S6338071 B2 JPS6338071 B2 JP S6338071B2 JP 59225644 A JP59225644 A JP 59225644A JP 22564484 A JP22564484 A JP 22564484A JP S6338071 B2 JPS6338071 B2 JP S6338071B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- group
- amino
- alk
- parts
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000000975 dye Substances 0.000 claims description 55
- 239000000985 reactive dye Substances 0.000 claims description 55
- 239000000460 chlorine Substances 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 16
- 229910052801 chlorine Inorganic materials 0.000 claims description 14
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 13
- 229910052731 fluorine Inorganic materials 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 13
- 239000011737 fluorine Substances 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 239000002243 precursor Substances 0.000 claims description 9
- ZFDLFHQAGYPRBY-UHFFFAOYSA-N chloro acetate Chemical compound CC(=O)OCl ZFDLFHQAGYPRBY-UHFFFAOYSA-N 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 6
- 229910019142 PO4 Inorganic materials 0.000 claims description 5
- 239000010452 phosphate Substances 0.000 claims description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 4
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 3
- 150000002790 naphthalenes Chemical class 0.000 claims description 3
- 125000004957 naphthylene group Chemical group 0.000 claims description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
- DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 claims 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical group [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 66
- -1 methoxy, ethoxy, propoxy, isopropoxy Chemical group 0.000 description 62
- 239000000243 solution Substances 0.000 description 44
- 238000005859 coupling reaction Methods 0.000 description 28
- 238000004043 dyeing Methods 0.000 description 23
- 239000004744 fabric Substances 0.000 description 23
- 239000011541 reaction mixture Substances 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- 230000008878 coupling Effects 0.000 description 20
- 238000010168 coupling process Methods 0.000 description 20
- 229920000742 Cotton Polymers 0.000 description 18
- 239000002253 acid Substances 0.000 description 17
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 16
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
- 230000005494 condensation Effects 0.000 description 12
- 238000003379 elimination reaction Methods 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 239000000835 fiber Substances 0.000 description 8
- 239000000543 intermediate Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- 238000009835 boiling Methods 0.000 description 7
- 238000009833 condensation Methods 0.000 description 7
- VMKJWLXVLHBJNK-UHFFFAOYSA-N cyanuric fluoride Chemical compound FC1=NC(F)=NC(F)=N1 VMKJWLXVLHBJNK-UHFFFAOYSA-N 0.000 description 7
- 239000003599 detergent Substances 0.000 description 7
- 239000013067 intermediate product Substances 0.000 description 7
- 239000011780 sodium chloride Substances 0.000 description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 6
- DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical compound [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 238000006482 condensation reaction Methods 0.000 description 5
- OARRHUQTFTUEOS-UHFFFAOYSA-N safranin Chemical compound [Cl-].C=12C=C(N)C(C)=CC2=NC2=CC(C)=C(N)C=C2[N+]=1C1=CC=CC=C1 OARRHUQTFTUEOS-UHFFFAOYSA-N 0.000 description 5
- 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 4
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
- 230000010933 acylation Effects 0.000 description 4
- 238000005917 acylation reaction Methods 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 230000019635 sulfation Effects 0.000 description 4
- 238000005670 sulfation reaction Methods 0.000 description 4
- ZUQOBHTUMCEQBG-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-1,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 ZUQOBHTUMCEQBG-UHFFFAOYSA-N 0.000 description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- XWBDWHCCBGMXKG-UHFFFAOYSA-N ethanamine;hydron;chloride Chemical compound Cl.CCN XWBDWHCCBGMXKG-UHFFFAOYSA-N 0.000 description 3
- 239000012433 hydrogen halide Substances 0.000 description 3
- 229910000039 hydrogen halide Inorganic materials 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- LJRGBERXYNQPJI-UHFFFAOYSA-M sodium;3-nitrobenzenesulfonate Chemical compound [Na+].[O-][N+](=O)C1=CC=CC(S([O-])(=O)=O)=C1 LJRGBERXYNQPJI-UHFFFAOYSA-M 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 210000002268 wool Anatomy 0.000 description 3
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 2
- UGEHFOSBNBEWMP-UHFFFAOYSA-N 2,3-diaminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1N UGEHFOSBNBEWMP-UHFFFAOYSA-N 0.000 description 2
- 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 2
- LNKCXUFJUDPYLP-UHFFFAOYSA-N 2-(2-chloroethylsulfonyl)-n-[2-(2-chloroethylsulfonyl)ethyl]ethanamine Chemical compound ClCCS(=O)(=O)CCNCCS(=O)(=O)CCCl LNKCXUFJUDPYLP-UHFFFAOYSA-N 0.000 description 2
- KVAQXZADNRRNCK-UHFFFAOYSA-N 2-(2-chloroethylsulfonyl)ethanamine;hydrochloride Chemical compound Cl.NCCS(=O)(=O)CCCl KVAQXZADNRRNCK-UHFFFAOYSA-N 0.000 description 2
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
- LDQMZKBIBRAZEA-UHFFFAOYSA-N 4-amino-2-aminobenzoic acid Natural products NC1=CC=C(C(O)=O)C(N)=C1 LDQMZKBIBRAZEA-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 150000001266 acyl halides Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical group C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 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
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 150000004696 coordination complex Chemical class 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 238000003795 desorption Methods 0.000 description 2
- 150000004985 diamines Chemical group 0.000 description 2
- VBQUDDWATQWCPP-UHFFFAOYSA-N ethylsulfonylbenzene Chemical compound CCS(=O)(=O)C1=CC=CC=C1 VBQUDDWATQWCPP-UHFFFAOYSA-N 0.000 description 2
- 239000003292 glue Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 238000009775 high-speed stirring Methods 0.000 description 2
- 125000001905 inorganic group Chemical group 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 125000000962 organic group Chemical group 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 238000009980 pad dyeing Methods 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 239000001103 potassium chloride Substances 0.000 description 2
- 235000011164 potassium chloride Nutrition 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
- 230000008569 process Effects 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000000661 sodium alginate Substances 0.000 description 2
- 235000010413 sodium alginate Nutrition 0.000 description 2
- 229940005550 sodium alginate Drugs 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- 229910021653 sulphate ion Inorganic materials 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 1
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-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
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- WCZNKVPCIFMXEQ-UHFFFAOYSA-N 2,3,5,6-tetramethylbenzene-1,4-diamine Chemical compound CC1=C(C)C(N)=C(C)C(C)=C1N WCZNKVPCIFMXEQ-UHFFFAOYSA-N 0.000 description 1
- NAWJZCSEYBQUGY-UHFFFAOYSA-N 2,3-diaminobenzamide Chemical compound NC(=O)C1=CC=CC(N)=C1N NAWJZCSEYBQUGY-UHFFFAOYSA-N 0.000 description 1
- HWKWYDXHMQQDQJ-UHFFFAOYSA-N 2,3-dibromopropanoyl chloride Chemical compound ClC(=O)C(Br)CBr HWKWYDXHMQQDQJ-UHFFFAOYSA-N 0.000 description 1
- RDMFEHLCCOQUMH-UHFFFAOYSA-N 2,4'-Diphenyldiamine Chemical compound C1=CC(N)=CC=C1C1=CC=CC=C1N RDMFEHLCCOQUMH-UHFFFAOYSA-N 0.000 description 1
- ZVDSMYGTJDFNHN-UHFFFAOYSA-N 2,4,6-trimethylbenzene-1,3-diamine Chemical compound CC1=CC(C)=C(N)C(C)=C1N ZVDSMYGTJDFNHN-UHFFFAOYSA-N 0.000 description 1
- BAHPQISAXRFLCL-UHFFFAOYSA-N 2,4-Diaminoanisole Chemical compound COC1=CC=C(N)C=C1N BAHPQISAXRFLCL-UHFFFAOYSA-N 0.000 description 1
- XAQCYASNAMYTQA-UHFFFAOYSA-N 2,4-diamino-5-methylbenzenesulfonic acid Chemical compound CC1=CC(S(O)(=O)=O)=C(N)C=C1N XAQCYASNAMYTQA-UHFFFAOYSA-N 0.000 description 1
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
- RRSOCWPIZGUDEQ-UHFFFAOYSA-N 2,5-diamino-4-chlorobenzenesulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=C(N)C=C1Cl RRSOCWPIZGUDEQ-UHFFFAOYSA-N 0.000 description 1
- UWQNVSVKVKKKOC-UHFFFAOYSA-N 2,5-diamino-4-methylbenzenesulfonic acid Chemical compound CC1=CC(N)=C(S(O)(=O)=O)C=C1N UWQNVSVKVKKKOC-UHFFFAOYSA-N 0.000 description 1
- QGNJPFLIBOTDKU-UHFFFAOYSA-N 2,5-diaminobenzene-1,3-disulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=C(N)C(S(O)(=O)=O)=C1 QGNJPFLIBOTDKU-UHFFFAOYSA-N 0.000 description 1
- VOPSFYWMOIKYEM-UHFFFAOYSA-N 2,5-diaminobenzene-1,4-disulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=C(N)C=C1S(O)(=O)=O VOPSFYWMOIKYEM-UHFFFAOYSA-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
- UONVFNLDGRWLKF-UHFFFAOYSA-N 2,5-diaminobenzoic acid Chemical compound NC1=CC=C(N)C(C(O)=O)=C1 UONVFNLDGRWLKF-UHFFFAOYSA-N 0.000 description 1
- JEMXXNLAGKMIQQ-UHFFFAOYSA-N 2,5-diethoxybenzene-1,4-diamine Chemical compound CCOC1=CC(N)=C(OCC)C=C1N JEMXXNLAGKMIQQ-UHFFFAOYSA-N 0.000 description 1
- MJGXYJUUKICJFL-UHFFFAOYSA-N 2,5-diethylbenzene-1,4-diamine Chemical compound CCC1=CC(N)=C(CC)C=C1N MJGXYJUUKICJFL-UHFFFAOYSA-N 0.000 description 1
- FOVOBTLEKSQTFG-UHFFFAOYSA-N 2,5-dimethoxybenzene-1,4-diamine Chemical compound COC1=CC(N)=C(OC)C=C1N FOVOBTLEKSQTFG-UHFFFAOYSA-N 0.000 description 1
- GQRWMXPYWGYLLC-UHFFFAOYSA-N 2-(2-bromoethylsulfonyl)-n-[2-(2-bromoethylsulfonyl)ethyl]ethanamine Chemical compound BrCCS(=O)(=O)CCNCCS(=O)(=O)CCBr GQRWMXPYWGYLLC-UHFFFAOYSA-N 0.000 description 1
- QPMJDDGJEQYRPK-UHFFFAOYSA-N 2-(2-bromoethylsulfonyl)ethanamine Chemical compound NCCS(=O)(=O)CCBr QPMJDDGJEQYRPK-UHFFFAOYSA-N 0.000 description 1
- WZXIERFNZJPFDL-UHFFFAOYSA-N 2-(2-chloroethylsulfonyl)-2-methylpropan-1-amine Chemical compound NCC(C)(C)S(=O)(=O)CCCl WZXIERFNZJPFDL-UHFFFAOYSA-N 0.000 description 1
- HPKMXOWNGSBOME-UHFFFAOYSA-N 2-(2-chloroethylsulfonyl)ethanamine Chemical compound NCCS(=O)(=O)CCCl HPKMXOWNGSBOME-UHFFFAOYSA-N 0.000 description 1
- NNIWOHHDCDRIDX-UHFFFAOYSA-N 2-(2-chloroethylsulfonyl)hexan-1-amine Chemical compound CCCCC(CN)S(=O)(=O)CCCl NNIWOHHDCDRIDX-UHFFFAOYSA-N 0.000 description 1
- SMVOLLJATMSUKJ-UHFFFAOYSA-N 2-(2-chloroethylsulfonyl)propan-2-amine Chemical compound CC(C)(N)S(=O)(=O)CCCl SMVOLLJATMSUKJ-UHFFFAOYSA-N 0.000 description 1
- RHTNDRUWGPTDOL-UHFFFAOYSA-N 2-amino-4-ethenylsulfonylbenzenesulfonic acid Chemical compound NC1=CC(S(=O)(=O)C=C)=CC=C1S(O)(=O)=O RHTNDRUWGPTDOL-UHFFFAOYSA-N 0.000 description 1
- IIQLVLWFQUUZII-UHFFFAOYSA-N 2-amino-5-(4-amino-3-carboxyphenyl)benzoic acid Chemical compound C1=C(C(O)=O)C(N)=CC=C1C1=CC=C(N)C(C(O)=O)=C1 IIQLVLWFQUUZII-UHFFFAOYSA-N 0.000 description 1
- PRUBFRVIKDZCCS-UHFFFAOYSA-N 2-amino-5-(aminomethyl)naphthalene-1,7-disulfonic acid Chemical compound NC1=CC=C2C(CN)=CC(S(O)(=O)=O)=CC2=C1S(O)(=O)=O PRUBFRVIKDZCCS-UHFFFAOYSA-N 0.000 description 1
- KTVWISLTJPDQQX-UHFFFAOYSA-N 2-amino-5-(aminomethyl)naphthalene-1-sulfonic acid Chemical compound NC1=CC=C2C(CN)=CC=CC2=C1S(O)(=O)=O KTVWISLTJPDQQX-UHFFFAOYSA-N 0.000 description 1
- ILFIVTCNXZZSQT-UHFFFAOYSA-N 2-amino-5-[(4-aminobenzoyl)amino]benzene-1,4-disulfonic acid Chemical compound C1=CC(N)=CC=C1C(=O)NC1=CC(S(O)(=O)=O)=C(N)C=C1S(O)(=O)=O ILFIVTCNXZZSQT-UHFFFAOYSA-N 0.000 description 1
- SDPWANLWDHGAMO-UHFFFAOYSA-N 2-bromo-4-ethenylsulfonylaniline Chemical compound NC1=CC=C(S(=O)(=O)C=C)C=C1Br SDPWANLWDHGAMO-UHFFFAOYSA-N 0.000 description 1
- OBCQPUSRAUNDAB-UHFFFAOYSA-N 2-bromoprop-2-enoyl chloride Chemical compound ClC(=O)C(Br)=C OBCQPUSRAUNDAB-UHFFFAOYSA-N 0.000 description 1
- HKIUHZIUGDGPEP-UHFFFAOYSA-N 2-chlorobenzene-1,4-diamine;2,5-dimethylbenzene-1,4-diamine Chemical compound NC1=CC=C(N)C(Cl)=C1.CC1=CC(N)=C(C)C=C1N HKIUHZIUGDGPEP-UHFFFAOYSA-N 0.000 description 1
- XOTUAMWIFRDGMZ-UHFFFAOYSA-N 2-chloroprop-2-enoyl chloride Chemical compound ClC(=C)C(Cl)=O XOTUAMWIFRDGMZ-UHFFFAOYSA-N 0.000 description 1
- FIEVMROEZSXCTB-UHFFFAOYSA-N 2-ethenylsulfonyl-n-(2-ethenylsulfonylethyl)ethanamine Chemical compound C=CS(=O)(=O)CCNCCS(=O)(=O)C=C FIEVMROEZSXCTB-UHFFFAOYSA-N 0.000 description 1
- VKHFJWGJEUDKBG-UHFFFAOYSA-N 2-ethenylsulfonylethanamine Chemical compound NCCS(=O)(=O)C=C VKHFJWGJEUDKBG-UHFFFAOYSA-N 0.000 description 1
- PKMIIMPMZIHGAJ-UHFFFAOYSA-N 2-ethoxybenzene-1,4-diamine Chemical compound CCOC1=CC(N)=CC=C1N PKMIIMPMZIHGAJ-UHFFFAOYSA-N 0.000 description 1
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- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
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- 229910052802 copper Inorganic materials 0.000 description 1
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- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
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- 125000005843 halogen group Chemical group 0.000 description 1
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- 229910052751 metal Inorganic materials 0.000 description 1
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- 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 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- BIYQLXLSSLKTNE-UHFFFAOYSA-N n-(3-aminophenyl)-2-hydroxyacetamide Chemical compound NC1=CC=CC(NC(=O)CO)=C1 BIYQLXLSSLKTNE-UHFFFAOYSA-N 0.000 description 1
- PEMGGJDINLGTON-UHFFFAOYSA-N n-(3-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=CC(N)=C1 PEMGGJDINLGTON-UHFFFAOYSA-N 0.000 description 1
- GOGZBMRXLADNEV-UHFFFAOYSA-N naphthalene-2,6-diamine Chemical compound C1=C(N)C=CC2=CC(N)=CC=C21 GOGZBMRXLADNEV-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
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- 235000019353 potassium silicate Nutrition 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
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- 239000000376 reactant Substances 0.000 description 1
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000344 soap Substances 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
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
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- 238000005406 washing Methods 0.000 description 1
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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
- C09B62/4401—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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
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Claims (1)
- ãç¹èš±è«æ±ã®ç¯å²ã ïŒ åŒ ãäžèšåŒäžã ã¯å Žåã«ãã€ãŠã¯ããã«ã¹ã«ãåºã§çœ®æãã
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åºã R1ã¯æ°ŽçŽ ããŸãã¯C1â4âã¢ã«ãã«ã R2ã¯æ°ŽçŽ ããããã¯åŒâalkâSO2âã®åºã alkã¯C2â6âã¢ã«ãã¬ã³ã ã¯âSO2âïŒâNHâCOïŒâCH2ïŒâ3â5SO2
âïŒâSO2âCH2âCHïŒCH2ïŒâNHâCOâ
CBrïŒCH2ïŒâNHâCOâCHBrâCH2BrïŒâ
NHâCOâCClïŒCH2ïŒâNHâCOâCHClâ
CH2ClãŸãã¯âNHâCOâCH2Clã®åºã ã¯âCHïŒCH2ãŸãã¯âCH2CH2âã®åºã ã¯ã¹ã«ãã¢ããããªã¹ã«ãã¢ãããã¹ãã¢
ããã¢ã»ããã·ãŸãã¯ããã²ã³ããããŠïŒžã¯ãã
çŽ ããŸãã¯å¡©çŽ ã ã¯åŒ åã¯åŒ ïŒåŒäžã D2ã¯ç¬ç«ã«ïŒ€ã®æå³ãæã¡ãããªã¢ãžã³éšå
ã¯åŒïŒ1*ïŒã®ããã¿ã¬ã³æ žã®OHåºã®ãªãæ¹ã®ç°
ã«çµåãååŒïŒ2*ïŒã®D2ã«çµåããŠããïŒãæ
å³ãããã®åå¿ææã ïŒ åŒ ïŒåŒäžã R3ã¯æ°ŽçŽ ãã¡ãã«ãåã¯ãšãã«ã R4ã¯æ°ŽçŽ ãŸãã¯âalkâSO2âã®åºã alkã¯C2â6âã¢ã«ãã¬ã³ã ã¯âSO2âã®åºã ã¯âCHïŒCH2ãŸãã¯âCH2CH2âã®åºã ã¯ã¹ã«ãã¢ããã¢ã»ããã·ãå¡©çŽ ããã¹ãã¢
ãããŸãã¯ããªã¹ã«ãã¢ãããã㊠ã¯ããçŽ ããŸãã¯å¡©çŽ ãæå³ããïŒã®ç¹èš±è«
æ±ã®ç¯å²ç¬¬ïŒé ã«èšèŒã®åå¿ææã ïŒ åŒ ïŒåŒäžã R5ã¯æ°ŽçŽ ãŸãã¯âalkâSO2âã®åºã alkã¯C2â6âã¢ã«ãã¬ã³ã ã¯âSO2âã®åºã ã¯âCHïŒCH2ãŸãã¯âCH2CH2âã®åºã ã¯ã¹ã«ãã¢ããã¢ã»ããã·ãå¡©çŽ ããã¹ãã¢
ãããŸãã¯ããªã¹ã«ãã¢ãããã㊠ã¯ããçŽ ããŸãã¯å¡©çŽ ãæå³ããïŒã®ç¹èš±è«
æ±ã®ç¯å²ç¬¬ïŒé ã«èšèŒã®åå¿ææã ïŒ åŒ ïŒåŒäžã R6ã¯æ°ŽçŽ ãŸãã¯âalkâSO2âã®åºã alkã¯C2â6âã¢ã«ãã¬ã³ã ã¯âSO2âã®åºã ã¯âCHïŒCH2ãŸãã¯âCH2CH2âã®åºã ã¯ã¹ã«ãã¢ããã¢ã»ããã·ãå¡©çŽ ããã¹ãã¢
ãããŸãã¯ããªã¹ã«ãã¢ãããã㊠ã¯ããçŽ ããŸãã¯å¡©çŽ ãæå³ããïŒã®ç¹èš±è«
æ±ã®ç¯å²ç¬¬ïŒé ã«èšèŒã®åå¿ææã ïŒ åŒ ïŒåŒäžã R7ã¯æ°ŽçŽ ãŸãã¯âalkâSO2âã®åºã alkã¯C2â6âã¢ã«ãã¬ã³ã ã¯âNHâCOâCHBrâCH2âBrïŒâNHâ
COâCBrïŒCH2ïŒãŸãã¯âSO2âã®åºã ã¯âCHïŒCH2ãŸãã¯âCH2CH2âã®åºã ã¯ã¹ã«ãã¢ããã¢ã»ããã·ãå¡©çŽ ããã¹ãã¢
ãããŸãã¯ããªã¹ã«ãã¢ãã ã¯ããçŽ ããŸãã¯å¡©çŽ ãããŠV1ãšV2ãšã¯äž
æ¹ãOHãããŠä»æ¹ãNH2ãæå³ããïŒã®ç¹èš±è«
æ±ã®ç¯å²ç¬¬ïŒé ã«èšèŒã®åå¿ææã ïŒ åŒ ã®ç¹èš±è«æ±ã®ç¯å²ç¬¬ïŒé ã«èšèŒã®åå¿ææã ïŒ åŒ ã®ç¹èš±è«æ±ã®ç¯å²ç¬¬ïŒé ã«èšèŒã®åå¿ææã ïŒ åŒ ã®ç¹èš±è«æ±ã®ç¯å²ç¬¬ïŒé ã«èšèŒã®åå¿ææã ïŒ åŒ ã®ç¹èš±è«æ±ã®ç¯å²ç¬¬ïŒé ã«èšèŒã®åå¿ææã ïŒïŒ åŒ ã®ç¹èš±è«æ±ã®ç¯å²ç¬¬ïŒé ã«èšèŒã®åå¿ææã ïŒïŒ åŒ ã®åå¿ææã®è£œé æ¹æ³ã«ãããŠã åŒ ã®ææãŸãã¯ãã®åé§çæç©ããäžèšåŒ ãäžèšåŒäžã ã¯å Žåã«ãã€ãŠã¯ããã«ã¹ã«ãåºã§çœ®æãã
ãŠããããšãã§ããããšãã¬ã³ãŸãã¯ãããã¬ã³
åºã R1ã¯æ°ŽçŽ ããŸãã¯C1â4âã¢ã«ãã«ã R2ã¯æ°ŽçŽ ããããã¯åŒâalkâSO2âã®åºã alkã¯C2â6âã¢ã«ãã¬ã³ã ã¯âSO2âïŒâNHâCOïŒCH2ïŒ3â5SO2â
ïŒâSO2âCH2âCHïŒCH2ïŒâNHâCOâ
CBrïŒCH2ïŒâNHâCOâCHBrâCH2BrïŒâ
NHâCOâCClïŒCH2ïŒâNHâCOâCHClâ
CH2ClããŸãã¯âNNâCOâCH2Clãã®åºã ã¯âCHïŒCH2ãŸãã¯âCH2CH2âã®åºã ã¯ã¹ã«ãã¢ããããªã¹ã«ãã¢ãããã¹ãã¢
ããã¢ã»ããã·åã¯ããã²ã³ããã㊠ã¯ããçŽ ããŸãã¯å¡©çŽ ã ã¯åŒ åã¯åŒ ïŒåŒäžãD2ã¯ç¬ç«ã«ïŒ€ã®æå³ãæã¡ãããªã¢
ãžã³éšåã¯åŒïŒ1*ïŒã®ããã¿ã¬ã³æ žã®OHåºã®ãª
ãæ¹ã®ç°ã«çµåãåã¯åŒïŒ2*ïŒã®D2ã«çµåããŠ
ããïŒãæå³ããã ã®åºãå°å ¥ããããã®åå¿æåãšåå¿ãããããš
ãç¹åŸŽãšããæ¹æ³ã
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH5795/83-6 | 1983-10-26 | ||
| CH579583 | 1983-10-26 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60110761A JPS60110761A (ja) | 1985-06-17 |
| JPS6338071B2 true JPS6338071B2 (ja) | 1988-07-28 |
Family
ID=4299432
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59225644A Granted JPS60110761A (ja) | 1983-10-26 | 1984-10-26 | åå¿ææãåã³ãã®è£œé æ¹æ³ |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4908436A (ja) |
| EP (1) | EP0141367B1 (ja) |
| JP (1) | JPS60110761A (ja) |
| DE (1) | DE3470169D1 (ja) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0233139B1 (de) * | 1986-01-10 | 1991-01-16 | Ciba-Geigy Ag | Reaktivfarbstoffe, deren Herstellung und Verwendung |
| DE3740649A1 (de) * | 1987-12-01 | 1989-06-15 | Bayer Ag | Reaktivfarbstoffe |
| US5243034A (en) * | 1988-12-21 | 1993-09-07 | Hoechst Aktiengesellschaft | Disazo dyestuffs having a triazine moiety and a fiberreactive group of vinylsulfone series |
| DE3843014A1 (de) * | 1988-12-21 | 1990-06-28 | Hoechst Ag | Wasserloesliche farbstoffe, verfahren zu ihrer herstellung und ihre verwendung |
| ES2061916T3 (es) * | 1989-01-04 | 1994-12-16 | Hoechst Ag | Colorantes reactivos con fibras solubles en agua, procedimiento para su obtencion y su aplicacion. |
| US5112959A (en) * | 1989-06-01 | 1992-05-12 | Sumitomo Chemical Company, Limited | Polyazo dye compounds having plural vinylsulfone type fiber reactive groups in one molecule |
| EP0419413A1 (de) * | 1989-09-22 | 1991-03-27 | Ciba-Geigy Ag | Verfahren zum FÀrben oder Bedrucken von Mischfasern aus cellulosehaltigen Fasermaterialien und Seide |
| EP0568876B1 (de) * | 1992-05-04 | 1996-08-28 | Bayer Ag | Reaktivfarbstoffe, deren Herstellung und Verwendung |
| US5478927A (en) * | 1993-02-04 | 1995-12-26 | Sumitomo Chemical Company, Limited | Bisazo compounds and use thereof as fiber reactive dyes |
| SG81913A1 (en) * | 1996-06-14 | 2001-07-24 | Ciba Sc Holding Ag | Reactive dyes, their preparation and use |
| US5952476A (en) * | 1998-08-21 | 1999-09-14 | Everlight Usa, Inc. | Red reactive dyestuffs |
| MXPA03000691A (es) | 2000-07-25 | 2003-06-04 | Dystar Textilfarben Gmbh & Co | Colorantes amarillos monoazo reactivos, metodos para su preparacion y uso de los mismos. |
| CN102391671B (zh) * | 2011-06-29 | 2016-07-13 | 倩接執å¯åå·¥è¡ä»œæéå ¬åž | äžç§å°ŒéŸæ©æŽ»æ§ææåå ¶å¶å€æ¹æ³ |
| TW202615593A (zh) | 2024-08-30 | 2026-04-16 | ç士åäºå çŸ éŠ¬ïŒç士ïŒæéå ¬åž | æææ··åç©åå ¶çšæŒç¹ç©æè²æå°è±ä¹çšé |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1265698C2 (de) * | 1961-05-06 | 1968-11-07 | Hoechst Ag | Verfahren zur Erzeugung von nassechten Faerbungen und Drucken |
| CA1032537A (en) * | 1973-04-04 | 1978-06-06 | Stefan Koller | Dyestuffs for synthetic fibres |
| DE2614550C3 (de) * | 1976-04-03 | 1981-06-25 | Cassella Ag, 6000 Frankfurt | Neue Reaktivfarbstoffe, ihre Herstellung und Verwendung zum FÀrben und Bedrucken von Cellulose sowie natÌrlichen und synthetischen Polyamidsubstraten |
| DE3033611A1 (de) * | 1980-09-06 | 1982-04-29 | Hoechst Ag, 6000 Frankfurt | Wasserloesliche disazoverbindungen, verfahren zu deren herstellung und ihre verwendung als farbstoffe |
| DE3120187A1 (de) * | 1981-05-21 | 1982-12-09 | Hoechst Ag, 6000 Frankfurt | Wasserloesliche disazoverbindungen, verfahren zu deren herstellung und ihre verwendung als farbstoffe |
| DE3263889D1 (en) * | 1981-07-21 | 1985-07-04 | Ciba Geigy Ag | Reactive dyestuffs, their preparation and their use |
| EP0074928A3 (de) * | 1981-09-16 | 1983-04-20 | Ciba-Geigy Ag | Reaktivfarbstoffe, deren Herstellung und Verwendung |
| DE3217812A1 (de) * | 1982-05-12 | 1983-11-17 | Hoechst Ag, 6230 Frankfurt | Monoazoverbindungen, verfahren zu ihrer herstellung und ihre verwendung als farbstoffe |
-
1984
- 1984-10-23 DE DE8484112760T patent/DE3470169D1/de not_active Expired
- 1984-10-23 EP EP84112760A patent/EP0141367B1/de not_active Expired
- 1984-10-26 JP JP59225644A patent/JPS60110761A/ja active Granted
-
1986
- 1986-10-23 US US06/921,849 patent/US4908436A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE3470169D1 (en) | 1988-05-05 |
| JPS60110761A (ja) | 1985-06-17 |
| EP0141367A1 (de) | 1985-05-15 |
| US4908436A (en) | 1990-03-13 |
| EP0141367B1 (de) | 1988-03-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |