JPH0388862A - Pyridone monoazo compound and method for dyeing or printing textile material using the same - Google Patents
Pyridone monoazo compound and method for dyeing or printing textile material using the sameInfo
- Publication number
- JPH0388862A JPH0388862A JP2034937A JP3493790A JPH0388862A JP H0388862 A JPH0388862 A JP H0388862A JP 2034937 A JP2034937 A JP 2034937A JP 3493790 A JP3493790 A JP 3493790A JP H0388862 A JPH0388862 A JP H0388862A
- Authority
- JP
- Japan
- Prior art keywords
- group
- acid
- optionally substituted
- aminonaphthalene
- substituted
- 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.)
- Granted
Links
- -1 Pyridone monoazo compound Chemical class 0.000 title claims abstract description 126
- 238000004043 dyeing Methods 0.000 title claims abstract description 22
- 239000000463 material Substances 0.000 title claims abstract description 13
- 238000000034 method Methods 0.000 title claims description 9
- 239000004753 textile Substances 0.000 title claims description 4
- 239000002253 acid Substances 0.000 claims abstract description 37
- 150000001875 compounds Chemical class 0.000 claims abstract description 27
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 17
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims abstract description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 10
- 125000004957 naphthylene group Chemical group 0.000 claims abstract description 9
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 8
- 125000005843 halogen group Chemical group 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 239000003513 alkali Substances 0.000 claims description 5
- 125000005650 substituted phenylene group Chemical group 0.000 claims description 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 230000009471 action Effects 0.000 claims description 3
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 2
- 125000004964 sulfoalkyl group Chemical group 0.000 claims description 2
- 239000000835 fiber Substances 0.000 abstract description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract description 5
- 239000004952 Polyamide Substances 0.000 abstract description 4
- 229910052736 halogen Inorganic materials 0.000 abstract description 4
- 229920002647 polyamide Polymers 0.000 abstract description 4
- 239000010985 leather Substances 0.000 abstract description 3
- 229920006306 polyurethane fiber Polymers 0.000 abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 21
- 125000001424 substituent group Chemical group 0.000 description 13
- 125000003545 alkoxy group Chemical group 0.000 description 10
- 229920003043 Cellulose fiber Polymers 0.000 description 9
- 125000001309 chloro group Chemical group Cl* 0.000 description 8
- 239000000975 dye Substances 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 235000002639 sodium chloride Nutrition 0.000 description 7
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 7
- SUZRRICLUFMAQD-UHFFFAOYSA-N N-Methyltaurine Chemical compound CNCCS(O)(=O)=O SUZRRICLUFMAQD-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 5
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000002657 fibrous material Substances 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 4
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- QRAXZXPSAGQUNP-UHFFFAOYSA-N 4-(methylamino)benzenesulfonic acid Chemical compound CNC1=CC=C(S(O)(=O)=O)C=C1 QRAXZXPSAGQUNP-UHFFFAOYSA-N 0.000 description 3
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 3
- 229960003080 taurine Drugs 0.000 description 3
- SSYPJXODUUFCQT-UHFFFAOYSA-N 1-(2-aminoethyl)-6-hydroxy-4-methylpyridin-2-one Chemical compound CC=1C=C(O)N(CCN)C(=O)C=1 SSYPJXODUUFCQT-UHFFFAOYSA-N 0.000 description 2
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 2
- GWIAAIUASRVOIA-UHFFFAOYSA-N 2-aminonaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(N)=CC=C21 GWIAAIUASRVOIA-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- MTJGVAJYTOXFJH-UHFFFAOYSA-N 3-aminonaphthalene-1,5-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 MTJGVAJYTOXFJH-UHFFFAOYSA-N 0.000 description 2
- ZCLXQTGLKVQKFD-UHFFFAOYSA-N 3-hydroxybenzenesulfonic acid Chemical compound OC1=CC=CC(S(O)(=O)=O)=C1 ZCLXQTGLKVQKFD-UHFFFAOYSA-N 0.000 description 2
- ALRHLSYJTWAHJZ-UHFFFAOYSA-N 3-hydroxypropionic acid Chemical compound OCCC(O)=O ALRHLSYJTWAHJZ-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
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 description 2
- IMUUNYPYNWXUBO-UHFFFAOYSA-N 4-aminobenzene-1,3-disulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1S(O)(=O)=O IMUUNYPYNWXUBO-UHFFFAOYSA-N 0.000 description 2
- NDYYJXGERWTRSD-UHFFFAOYSA-N 4-aminonaphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=C2C(N)=CC(S(O)(=O)=O)=CC2=C1 NDYYJXGERWTRSD-UHFFFAOYSA-N 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
- QNVNLUSHGRBCLO-UHFFFAOYSA-N 5-hydroxybenzene-1,3-dicarboxylic acid Chemical compound OC(=O)C1=CC(O)=CC(C(O)=O)=C1 QNVNLUSHGRBCLO-UHFFFAOYSA-N 0.000 description 2
- HKTWHHAJDJCUPC-UHFFFAOYSA-N 7-aminonaphthalene-1,3,5-trisulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 HKTWHHAJDJCUPC-UHFFFAOYSA-N 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 2
- 229920000297 Rayon Polymers 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 125000005521 carbonamide group Chemical group 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000003792 electrolyte Substances 0.000 description 2
- LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
- IJFXRHURBJZNAO-UHFFFAOYSA-N meta--hydroxybenzoic acid Natural products OC(=O)C1=CC=CC(O)=C1 IJFXRHURBJZNAO-UHFFFAOYSA-N 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 239000010446 mirabilite Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 229960003512 nicotinic acid Drugs 0.000 description 2
- 235000001968 nicotinic acid Nutrition 0.000 description 2
- 239000011664 nicotinic acid Substances 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 239000000985 reactive dye Substances 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
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 238000010025 steaming Methods 0.000 description 2
- 229950000244 sulfanilic acid Drugs 0.000 description 2
- 210000004243 sweat Anatomy 0.000 description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 2
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 2
- LZXHHNKULPHARO-UHFFFAOYSA-M (3,4-dichlorophenyl)methyl-triphenylphosphanium;chloride Chemical compound [Cl-].C1=C(Cl)C(Cl)=CC=C1C[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 LZXHHNKULPHARO-UHFFFAOYSA-M 0.000 description 1
- ZSRDNPVYGSFUMD-UHFFFAOYSA-N (3-chlorophenyl)methanol Chemical compound OCC1=CC=CC(Cl)=C1 ZSRDNPVYGSFUMD-UHFFFAOYSA-N 0.000 description 1
- YMVFJGSXZNNUDW-UHFFFAOYSA-N (4-chlorophenyl)methanamine Chemical compound NCC1=CC=C(Cl)C=C1 YMVFJGSXZNNUDW-UHFFFAOYSA-N 0.000 description 1
- PTHGDVCPCZKZKR-UHFFFAOYSA-N (4-chlorophenyl)methanol Chemical compound OCC1=CC=C(Cl)C=C1 PTHGDVCPCZKZKR-UHFFFAOYSA-N 0.000 description 1
- VRYLXDRQGIZWOU-UHFFFAOYSA-N (4-hydroxyphenyl)methanesulfonic acid Chemical compound OC1=CC=C(CS(O)(=O)=O)C=C1 VRYLXDRQGIZWOU-UHFFFAOYSA-N 0.000 description 1
- HMTSWYPNXFHGEP-UHFFFAOYSA-N (4-methylphenyl)methanamine Chemical compound CC1=CC=C(CN)C=C1 HMTSWYPNXFHGEP-UHFFFAOYSA-N 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- ONZWNZGVZFLMNZ-UHFFFAOYSA-N 1-aminonaphthalene-2-sulfonic acid Chemical compound C1=CC=C2C([NH3+])=C(S([O-])(=O)=O)C=CC2=C1 ONZWNZGVZFLMNZ-UHFFFAOYSA-N 0.000 description 1
- PWJNDVAKQLOWRZ-UHFFFAOYSA-N 1-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=CC=C2C(O)=C(S(O)(=O)=O)C=CC2=C1 PWJNDVAKQLOWRZ-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- PJAGJTVXNXUWDV-UHFFFAOYSA-N 2-(2-amino-3-methylphenyl)ethanol Chemical compound CC1=CC=CC(CCO)=C1N PJAGJTVXNXUWDV-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- XAFUTAXWBWPYMU-UHFFFAOYSA-N 2-amino-4-ethylbenzenesulfonic acid Chemical compound CCC1=CC=C(S(O)(=O)=O)C(N)=C1 XAFUTAXWBWPYMU-UHFFFAOYSA-N 0.000 description 1
- LDCCBULMAFILCT-UHFFFAOYSA-N 2-aminobenzene-1,4-disulfonic acid Chemical compound NC1=CC(S(O)(=O)=O)=CC=C1S(O)(=O)=O LDCCBULMAFILCT-UHFFFAOYSA-N 0.000 description 1
- BRWJTSYXNZYZRH-UHFFFAOYSA-N 2-aminonaphthalene-1,3-disulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(N)=C(S(O)(=O)=O)C=C21 BRWJTSYXNZYZRH-UHFFFAOYSA-N 0.000 description 1
- YAIKCRUPEVOINQ-UHFFFAOYSA-N 2-aminonaphthalene-1,5-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC2=C(S(O)(=O)=O)C(N)=CC=C21 YAIKCRUPEVOINQ-UHFFFAOYSA-N 0.000 description 1
- 125000005999 2-bromoethyl group Chemical group 0.000 description 1
- 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 description 1
- VKPPFDPXZWFDFA-UHFFFAOYSA-N 2-chloroethanamine Chemical compound NCCCl VKPPFDPXZWFDFA-UHFFFAOYSA-N 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 229940093475 2-ethoxyethanol Drugs 0.000 description 1
- UFYHBOYUGAEJSQ-UHFFFAOYSA-N 2-hydroxynaphthalene-1,5-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC2=C(S(O)(=O)=O)C(O)=CC=C21 UFYHBOYUGAEJSQ-UHFFFAOYSA-N 0.000 description 1
- SGBQUMZTGSQNAO-UHFFFAOYSA-N 2-hydroxynaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(O)=CC=C21 SGBQUMZTGSQNAO-UHFFFAOYSA-N 0.000 description 1
- ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- YPWSASPSYAWQRK-UHFFFAOYSA-N 2-pyridin-3-ylethanol Chemical compound OCCC1=CC=CN=C1 YPWSASPSYAWQRK-UHFFFAOYSA-N 0.000 description 1
- RGIIAYDCZSXHGL-UHFFFAOYSA-N 2-pyridin-4-ylethanesulfonic acid Chemical compound OS(=O)(=O)CCC1=CC=NC=C1 RGIIAYDCZSXHGL-UHFFFAOYSA-N 0.000 description 1
- XRDCAKRYIFMDMC-UHFFFAOYSA-N 3-(methylamino)benzenesulfonic acid Chemical compound CNC1=CC=CC(S(O)(=O)=O)=C1 XRDCAKRYIFMDMC-UHFFFAOYSA-N 0.000 description 1
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- SQYUJKVKVFILNB-UHFFFAOYSA-N methyl 2-amino-4-[(2,5-dichlorophenyl)carbamoyl]benzoate Chemical compound C1=C(N)C(C(=O)OC)=CC=C1C(=O)NC1=CC(Cl)=CC=C1Cl SQYUJKVKVFILNB-UHFFFAOYSA-N 0.000 description 1
- DAKZISABEDGGSV-UHFFFAOYSA-N n-(2-aminoethyl)acetamide Chemical compound CC(=O)NCCN DAKZISABEDGGSV-UHFFFAOYSA-N 0.000 description 1
- YGBYFDPEECMAJJ-UHFFFAOYSA-N n-(2-methylpropyl)naphthalen-2-amine Chemical compound C1=CC=CC2=CC(NCC(C)C)=CC=C21 YGBYFDPEECMAJJ-UHFFFAOYSA-N 0.000 description 1
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
- NRZRRZAVMCAKEP-UHFFFAOYSA-N naphthionic acid Chemical compound C1=CC=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 NRZRRZAVMCAKEP-UHFFFAOYSA-N 0.000 description 1
- PODAMDNJNMAKAZ-UHFFFAOYSA-N penta-2,3-diene Chemical group CC=C=CC PODAMDNJNMAKAZ-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 238000005502 peroxidation Methods 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- DVECLMOWYVDJRM-UHFFFAOYSA-N pyridine-3-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=CN=C1 DVECLMOWYVDJRM-UHFFFAOYSA-N 0.000 description 1
- ZARCYQBIHIVLOO-UHFFFAOYSA-N pyridine;triazine Chemical group C1=CC=NC=C1.C1=CN=NN=C1 ZARCYQBIHIVLOO-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 102200014657 rs121434437 Human genes 0.000 description 1
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
- 235000019254 sodium formate Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 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
- 229940080313 sodium starch Drugs 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
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Landscapes
- Coloring (AREA)
Abstract
Description
【発明の詳細な説明】
〈産業上の利用分野〉
本発明はヒドロキシル基及び／又はアミド基を含有する
材料、特にセルロース繊維、天然又は合戒ポリアミド繊
維、ポリウレタン繊維あるいは皮革等、更にはそれらの
混紡繊維を染色及び捺染するに適し、針先堅牢かつ耐湿
潤堅牢な黄色染色を可能にする改良された化合物、並び
にその適用に関する。Detailed Description of the Invention <Industrial Application Field> The present invention relates to materials containing hydroxyl groups and/or amide groups, particularly cellulose fibers, natural or synthetic polyamide fibers, polyurethane fibers, leather, etc. The present invention relates to an improved compound suitable for dyeing and printing blended fibers, which enables needlepoint-fast and wet-fast yellow dyeing, and its application.
〈従来の技術〉
同一分子内にビニルスルホン系反応基と、ピリジニウム
トリアジン反応基とを有する化合物は、特開昭６０−１
７３０６０公報において公知であるが、染色性能面、例
えばビルドアツプ性において不充分であり、更にレベル
アップが望まれている。<Prior art> A compound having a vinyl sulfone reactive group and a pyridinium triazine reactive group in the same molecule is disclosed in Japanese Patent Application Laid-open No. 60-1
Although it is known in Japanese Patent No. 73060, it is insufficient in terms of dyeing performance, such as build-up property, and further improvement is desired.
〈発明が解決しようとする課題〉
従来、種々の反応染料は繊維材料の染色及び捺染の分野
に広く使用されている。しかし現在の技術水準は、特定
の染色法に対する適性に関する高い要求水準ならびに染
色物の堅牢性に関する要求の高度化の点から満足すべき
ものとは言えない。<Problems to be Solved by the Invention> Conventionally, various reactive dyes have been widely used in the fields of dyeing and printing textile materials. However, the current state of the art cannot be said to be satisfactory in view of the high requirements regarding suitability for specific dyeing methods and the increasingly sophisticated requirements regarding the fastness of dyed products.
前記した公知の反応染料は、溶解性、染色性能（例えば
ビルドアツプ性等）及び堅牢性の面で不十分であり、更
に改良された染料の提供が強く望まれている。The above-mentioned known reactive dyes are insufficient in solubility, dyeing performance (for example, build-up properties, etc.), and fastness, and there is a strong desire to provide further improved dyes.
ビルドアツプ性に優れることの重要性は、染色方法の経
済性に対する要求レベルがますます高くなってきている
今日、極めて重要な要素である。The importance of having excellent build-up properties is an extremely important factor in today's world, where demands for economic efficiency of dyeing methods are becoming higher and higher.
本発明者らは、上述の公知染料の欠点を改良し、さらに
染料に対して要求される要件を広く満足できる新規な化
合物を見い出す目的で鋭意検討した結果、本発明を完成
した。The present inventors completed the present invention as a result of intensive studies aimed at improving the drawbacks of the above-mentioned known dyes and finding a new compound that can broadly satisfy the requirements required for dyes.
〈課題を解決する為の手段〉
本発明は、遊離酸の形で下記一般式（１）〔式中、Ｘは
、−Ｎ−Ａ−Ｚ２、 Ｎ Ｒ２Ｒｓ。<Means for Solving the Problems> The present invention provides a free acid having the following general formula (1) [wherein, X is -N-A-Z2, N R2Rs].
１
一０Ｒ４または−ＳＲ，を、Ｙは置換もしくは無置換の
ピリジニオ基を、Ｚ、およびＺ２は互いに独立に−Ｓ○
、ＣＨ＝ＣＨ２又は
−Ｓ Ｏ２ＣＨ２ＣＨ２Ｚ ’ を表し、Ｚ′はアルカ
リの作用で脱離する基を表す。Ａは置換されていてもよ
いフェニレン、ナフチレンまたはアルキレン基を表す。1 -R4 or -SR, Y is a substituted or unsubstituted pyridinio group, Z and Z2 are each independently -S○
, CH=CH2 or -S O2CH2CH2Z', and Z' represents a group that is eliminated by the action of an alkali. A represents an optionally substituted phenylene, naphthylene or alkylene group.
Ｒ，は水素又は置換されていてもよいアルキル基を、Ｒ
ｚ、Ｒｓ、ＲａおよびＲ３は互いに独立に水素または置
換されていてもよいアルキル、フェニル、ナフチルもし
くはベンジル基を表す。Ｒ６は水素又は置換されていて
もよいアルキル基を、Ｒ７は水素、シアノ基、カルバモ
イル基、スルホ基、スルホアルキル基またはハロゲン基
を、Ｒｓはアルキル基を表す。Ｄは置換されていてもよ
いフェニレンまたはナフチレン基を表す。Ｗはアルキレ
ン基をあられす。〕
で示されるピリドンモノアゾ化合物およびそれを用いる
ことを特徴とするＷａ！ｉ材料の染色または捺染方法を
提供するものである。R represents hydrogen or an optionally substituted alkyl group;
z, Rs, Ra and R3 each independently represent hydrogen or an optionally substituted alkyl, phenyl, naphthyl or benzyl group. R6 represents hydrogen or an optionally substituted alkyl group, R7 represents hydrogen, a cyano group, a carbamoyl group, a sulfo group, a sulfoalkyl group, or a halogen group, and Rs represents an alkyl group. D represents an optionally substituted phenylene or naphthylene group. W represents an alkylene group. ] A pyridone monoazo compound represented by and Wa! characterized by using the same. This invention provides a method for dyeing or printing i-materials.
一般式（Ｉ）において、Ａで表されるフェニレンおよび
ナフチレンとしては、好ましくはメチル、エチル、メト
キシ、エトキシ、クロロ、ブロモ及びスルホの群から選
ばれる、１又は２個の置換基により置換されていてもよ
いフェニレン又は、スルホで置換されていてもよいナフ
チレンが例示され、例えば、
じている結合を意味する。）
等をあげることができる。あるいは、
表されるアルキレンとしては下記式、
また、
Ａで
Ｒ”
（ＣＨ２）−一〇−
（ＣＨ２）ｍ ＊
（ロ）
じている結合を意味する。ａｌｋは１乃至６個の炭素原
子を有するポリメチレン基またはその枝別れ異性体、Ｒ
′は水素、塩素、臭素、フッ素、ヒドロキシ、スルファ
ト、ｌ乃至４個の炭素原子を有するアシルオキシ、シア
ノ、カルボキシ、１乃至５個の炭素原子を有するアルコ
キシカルボニル、またはカルバモイル、Ｒ”は、水素又
はＣ１〜６アルキル、ａｌｋ’は互いに独立的に２乃至
６個の炭素原子を有するポリメチレン基またはその枝別
れ異性体を意味し、ａｌｋ’ とＲ”は互いにメチレン
基を通じて環を懲戒してもよい。ｎは１乃至６、ｍは１
乃至６の整数である。）で示される基があげられる。In general formula (I), phenylene and naphthylene represented by A are preferably substituted with one or two substituents selected from the group of methyl, ethyl, methoxy, ethoxy, chloro, bromo and sulfo. Examples include phenylene which may be substituted with sulfo, and naphthylene which may be substituted with sulfo. ), etc. Alternatively, the represented alkylene refers to the following formula, and also refers to a bond in which A represents R" (CH2)-10- (CH2)m * (b). alk represents 1 to 6 carbon atoms a polymethylene group or its branched isomer, R
' is hydrogen, chlorine, bromine, fluorine, hydroxy, sulfato, acyloxy having 1 to 4 carbon atoms, cyano, carboxy, alkoxycarbonyl having 1 to 5 carbon atoms, or carbamoyl; R'' is hydrogen or C1-6 alkyl and alk' each independently mean a polymethylene group having 2 to 6 carbon atoms or a branched isomer thereof, and alk' and R'' may mutually terminate the ring through a methylene group. . n is 1 to 6, m is 1
It is an integer from 6 to 6. ) can be mentioned.
上記（ａ）、（ｂ）および（Ｃ）においてａｌｋで表さ
れるポリメチレン基は好ましくはメチレン、エチレン、
メチルメチレン、プロピレン、ブチレンである。The polymethylene group represented by alk in (a), (b) and (C) above is preferably methylene, ethylene,
These are methylmethylene, propylene, and butylene.
Ｒ”としては水素、メチル、エチル、プロピル、インプ
ロピル、ブチル、インブチル、５ｅｃ−ブチル、ｔｅｒ
ｔ−ブチル、ペンチル、ヘキシルなどが例示され、好ま
しくは水素である。ａｌｋ’で表されるポリメチレン基
は好ましくはエチレン、プロピレンまたはブチレンであ
る。R" is hydrogen, methyl, ethyl, propyl, inpropyl, butyl, inbutyl, 5ec-butyl, ter
Examples include t-butyl, pentyl, hexyl, etc., with hydrogen being preferred. The polymethylene group represented by alk' is preferably ethylene, propylene or butylene.
ｎ、ｍの表す数は好ましくは互いに独立に２．３または
４である。The numbers n and m preferably represent 2.3 or 4 independently of each other.
Ｄとしては、好ましくはメチル、エチル、メトキシ、エ
トキシ、クロロ、ブロモ及びスルホの群から選ばれる、
１又は２個の置換基により置換されていてもよいフェニ
レン又は、スルホで置換されていてもよいナフチレンが
例示され、例えば、（式中、＊＊で示した結合は、−Ｎ
＝Ｎ−基に通じている結合を意味する。）
等をあげることができる。D is preferably selected from the group of methyl, ethyl, methoxy, ethoxy, chloro, bromo and sulfo.
Examples include phenylene which may be substituted with one or two substituents or naphthylene which may be substituted with sulfo.
= means a bond leading to the N- group. ), etc.
中でも、アゾ基のオルソ位にスルホ基を有するものが好
ましく、例えば、
（式中、＊＊で示した結合は前記の意味を有する。）
等を挙げることができる。Among these, those having a sulfo group at the ortho position of the azo group are preferred, such as (in the formula, the bond indicated by ** has the above-mentioned meaning).
Ｚｏで示されるアルカリの作用で脱離する基としては、
例えば、硫酸エステル、チオ硫酸エステル、リン酸エス
テル、酢酸エステル、ハロゲン等がこれに該当し、中で
も硫酸エステルが好ましい。Groups that are eliminated by the action of alkali, represented by Zo, are:
For example, sulfuric esters, thiosulfuric esters, phosphoric esters, acetic esters, halogens, etc. fall under this category, and among them, sulfuric esters are preferred.
Ｒ，およびＲ６で示される置換基を有していてもよいア
ルキルとしては、ｃｌ〜Ｃ４のアルキルが好ましく、置
換されていてもよい基としては、ヒドロキシ、シアノ、
アルコキシ、ハロゲン、カルバモイル、カルボキシ、ア
ルコキシカルボニル、アルキルカルボニルオキシ、スル
ホおよびスルファモイルが好ましい。The optionally substituted alkyl represented by R and R6 is preferably a Cl to C4 alkyl, and the optionally substituted group includes hydroxy, cyano,
Preferred are alkoxy, halogen, carbamoyl, carboxy, alkoxycarbonyl, alkylcarbonyloxy, sulfo and sulfamoyl.
特に好ましいＲ１およびＲ６としては、例えば、水素、
メチノベエチル、ｎ−プロピル、１ｓｏ−ブロビノペｎ
−ブチル、１ｓｏ−ブチル、５ｅｃ−ブチル、２−ヒド
ロキシエチル、２−ヒドロキシプロピル、３−ヒドロキ
シプロピルペ ２−ヒドロキシブチル、３−ヒドロキシ
ブチル、４−ヒドロキシブチル、２．３−ジヒドロキシ
プロピル、３．４−ジヒドロキシブチル、シアノメチル
、２−シアノエチル、３−シアノプロピル、メトキシメ
チル、エトキシエチルペ ２−メトキシエチル、２−
エトキシエチル、３−メトキシプロピル、３−エトキシ
プロピル、２−ヒドロキシ−３−メトキシプロピル、ク
ロロメチル、ブロモメチル、２−クロロエチル、２−ブ
ロモエチル、３−クロロプロピル、３−ブロモプロピル
、４−クロロブチル、４−ブロモブチル、カルボキシメ
チル、２−カルボキシエチル、３−カルボキシプロピル
、４−カルボ キシブチル、１．２−ジカルボキシエチ
ノペ力ルバモイルメチル、２−カルバモイルエチル、３
−カルバモイルプロピル、４−カルバモイルブチル、メ
トキシカルボニルメチル、エトキシカルボニルメチル、
２−メトキシカルボニルエチル、２−エトキシカルボニ
ルエチル、３−メトキシカルボニルプロピル、３−エト
キシカルボニルプロビル、４−メトキシカルボニルブチ
ル、４−エトキシカルボニルブチル、メチルカルボニル
オキシメチル、エチルカルボニルオキシメチル、２−メ
チル力もルポニルオキシエチル、２−エチルカルボニル
オキシエチル、３−メチルカルボニルオキシプロピル、
３−エチルカルボニルオキシプロビル、４−メチルカル
ボニルオキシブチル、４−エチルカルボニルオキシブチ
ル、スルホメチル、２−スルホエチル、３−スルホプロ
ピル、４−スルホブチル、スルファモイルメチル、２−
スルファモイルエチル、３−スルファモイルプロピル、
４−スルファモイルブチルをあげることができる。中で
も特に 好ましくは、水素、メチルまたはエチルである
。Particularly preferable R1 and R6 include, for example, hydrogen,
Methinobethyl, n-propyl, 1so-brobinopene
-butyl, 1so-butyl, 5ec-butyl, 2-hydroxyethyl, 2-hydroxypropyl, 3-hydroxypropylpe 2-hydroxybutyl, 3-hydroxybutyl, 4-hydroxybutyl, 2,3-dihydroxypropyl, 3. 4-dihydroxybutyl, cyanomethyl, 2-cyanoethyl, 3-cyanopropyl, methoxymethyl, ethoxyethylpe 2-methoxyethyl, 2-
Ethoxyethyl, 3-methoxypropyl, 3-ethoxypropyl, 2-hydroxy-3-methoxypropyl, chloromethyl, bromomethyl, 2-chloroethyl, 2-bromoethyl, 3-chloropropyl, 3-bromopropyl, 4-chlorobutyl, 4 -bromobutyl, carboxymethyl, 2-carboxyethyl, 3-carboxypropyl, 4-carboxybutyl, 1,2-dicarboxyethinopelbamoylmethyl, 2-carbamoylethyl, 3
-carbamoylpropyl, 4-carbamoylbutyl, methoxycarbonylmethyl, ethoxycarbonylmethyl,
2-methoxycarbonylethyl, 2-ethoxycarbonylethyl, 3-methoxycarbonylpropyl, 3-ethoxycarbonylpropyl, 4-methoxycarbonylbutyl, 4-ethoxycarbonylbutyl, methylcarbonyloxymethyl, ethylcarbonyloxymethyl, 2-methyl Power is also luponyloxyethyl, 2-ethylcarbonyloxyethyl, 3-methylcarbonyloxypropyl,
3-ethylcarbonyloxypropyl, 4-methylcarbonyloxybutyl, 4-ethylcarbonyloxybutyl, sulfomethyl, 2-sulfoethyl, 3-sulfopropyl, 4-sulfobutyl, sulfamoylmethyl, 2-
Sulfamoylethyl, 3-sulfamoylpropyl,
4-sulfamoylbutyl can be mentioned. Particularly preferred among these are hydrogen, methyl, and ethyl.
Ｒ２及びＲ５で表される置換されていてもよいアルキル
としては、例えば、１〜４個の炭素原子を有するアルコ
キシ、スルホ、カルボキシ、ヒドロキシ、クロロ、フェ
ニル及びスルフアートの群から選ばれる、１又は２個の
置換基により置換されていてもよい炭素原子１〜４個を
有するアルキルが好ましい。The optionally substituted alkyl represented by R2 and R5 is, for example, 1 or 2 selected from the group of alkoxy, sulfo, carboxy, hydroxy, chloro, phenyl, and sulfate having 1 to 4 carbon atoms. Preference is given to alkyl having 1 to 4 carbon atoms, which may be substituted with 1 to 4 substituents.
中でも特に好ましくは、メチノベエチル、ｎ −プロピ
ル、１ｓｏ−プロピノペｎ−ブチル、ｌｓ〇−ブチル、
５ｅＣ−ブチル、β−ヒドロキシエチル、β−スルフア
ートエチル、β−スルホエチル、β−メトキシエチル及
びβ−カルボキシエチル等が挙げられる。Particularly preferred among these are methinobeethyl, n-propyl, 1so-propinopene n-butyl, ls〇-butyl,
Examples include 5eC-butyl, β-hydroxyethyl, β-sulfatoethyl, β-sulfoethyl, β-methoxyethyl, and β-carboxyethyl.
又、Ｒ２及びＲ５で表される置換されていてもよいフェ
ニルとしては、例えば、１〜４個の炭素原子を有するア
ルキル、ｌ〜４個の炭素原子を有するアルコキシ、スル
ホ、カルボキシ、クロロ及びプロその群から選ばれる、
１又は２個の置換基により置換されていてもよいフェニ
ルが好ましい。In addition, the optionally substituted phenyl represented by R2 and R5 includes, for example, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, sulfo, carboxy, chloro, and propylene. selected from that group,
Phenyl optionally substituted with one or two substituents is preferred.
中でも特に好ましくは、フェニル、２−１３−又は４−
スルホフェニル、２，４−又は２，５−ジスルホフェニ
ル、２−１３−又は４−カルボキシフェニル、２−１３
−又は４−クロロフェニル、２−１３−又は４−メチル
フェニル及び２−３−又は４−メトキシフェニル等が挙
げられる。Among them, phenyl, 2-13- or 4-
Sulfophenyl, 2,4- or 2,5-disulfophenyl, 2-13- or 4-carboxyphenyl, 2-13
- or 4-chlorophenyl, 2-13- or 4-methylphenyl, and 2-3- or 4-methoxyphenyl.
又、Ｒ２及びＲ５で表される置換されていてもよいナフ
チルとしては、例えば、ヒドロキシ、カルボキシ、スル
ホ、１〜４個の炭素原子を有するアルキノペ１〜４個の
炭素原子を有するアルコキシ及びクロロの群から選ばれ
る、１，２又は３個の置換基により置換されていてもよ
いナフチルが好ましい。Further, the optionally substituted naphthyl represented by R2 and R5 includes, for example, hydroxy, carboxy, sulfo, alkinope having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, and chloro. Naphthyl optionally substituted with 1, 2 or 3 substituents selected from the group is preferred.
中でも特に好ましくは、２−１３−１４−１５．６−１
７−又は８−スルホ−１−ナフチル、１−１５−１６−
１７−又は８−スルホ−２−ナフチル、１．５−１５．
７−１６．８−１４．８．４．７−１３．８−１４，６
−１３，７−又は３，６−ジスルホ−２−ナフチル、４
．６，８．２．４．７−又は３，６．８−）ジスルホ−
１−ナフチル、１，５．７−１４．６，８−又は３．６
．８−）ジスルホ−２−ナフチル等が挙げられる。Among them, particularly preferred is 2-13-14-15.6-1
7- or 8-sulfo-1-naphthyl, 1-15-16-
17- or 8-sulfo-2-naphthyl, 1.5-15.
7-16.8-14.8.4.7-13.8-14,6
-13,7- or 3,6-disulfo-2-naphthyl, 4
．． 6,8.2.4.7- or 3,6.8-)disulfo-
1-naphthyl, 1,5.7-14.6,8- or 3.6
．． 8-) Disulfo-2-naphthyl and the like.
又、Ｒ２及びＲ３で表される置換されていてもよいベン
ジルとしては、例えば、１〜４個の炭素原子を有するア
ルキル、１〜４個の炭素原子を有するアルコキシ、スル
ホ及びクロロの群から選ばれる、１又は２個の置換基に
より置換されていてもよいベンジルが好ましい。Further, the optionally substituted benzyl represented by R2 and R3 is selected from the group of, for example, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, sulfo, and chloro. Benzyl optionally substituted with one or two substituents is preferred.
中でも特に好ましくは、ベンジル、２−１３−又は４−
スルホベンジル等が挙げられる。Among these, benzyl, 2-13- or 4-
Examples include sulfobenzyl.
本発明においては、Ｒ２及びＲ５のいずれか一方が水素
、メチル又はエチルであり、他方がＣ３〜。In the present invention, either R2 or R5 is hydrogen, methyl or ethyl, and the other is C3~.
アルキル、Ｃ１〜、アルコキシ、スルホ、カルボキシ又
はハロゲノで置換されていてもよいフェニルである場合
が染料特性上特に好ましい。In terms of dye properties, phenyl which may be substituted with alkyl, C1~, alkoxy, sulfo, carboxy or halogeno is particularly preferred.
前記一般式（Ｉ）において、Ｘが−ＮＲ２Ｒ３であると
き、そのような基を形成するために用いられる、ＨＮ
Ｒ２Ｒｓで示される化合物としては、例えば、アンモニ
アあるいはＩ−アミノベンゼン、１−アミノ−２−、−
３−又は−４−メチル−ベンゼン、１−アミノ−３，４
−又は−３，５−ジメ″ルベンゼン、ｌ−アミノ−２−
、−３−又は−４−エチルベンゼン、１−アミノ−２−
３−又は−４−メトキシベンゼン、ニーアミノ−２−−
３−又は−４−エトキシベンゼン、ニーアミノ−２−−
３−又は−４−クロルベンゼン、３−又は４〜アミノ−
フェニルメタンスルホンＬ ２−１３−又は４−アミノ
ベンゼンスルホン酸、３−メチルアミノベンゼンスルホ
ン酸、３−二チルアミノベンゼン スルホン酸、４−メ
チルアミノベンゼンスルホン酸、４−エチルアミノベン
ゼンスルホン酸、５−アミノベンゼン−１，３−ジスル
ホン酸、６−アミノベンゼン−１，３−ジスルホン酸、
６−アミノベンゼン−１，４−ジスルホン酸、４−アミ
ノベンゼン−１，２−ジスルホン酸、４−アミノ−５−
メチルベンゼン−１２−ジスルホン酸、２−１３−又は
４−アミノ安息香酸、５−アミノベンゼン−１，３−ジ
カルボン酸、５−アミノ−２−ヒドロキシベンゼンスル
ホン酸、４−アミノ−２−ヒドロキシベンゼンスルホン
酸、５−アミ７−２−エトキシベンゼンスルホン酸、Ｎ
−メチルアミノベンゼン、Ｎ−エチルアミノベンゼン、
１−メチルアミノ−３−又は−４−メチルベンゼン、１
−エチルアミノ−４−クロルベンゼン、１−エチルアミ
ノ−３−又１！−４−メチルベンゼン、１−（２−ヒド
ロキシエチル）−アミノ−３−メチルベン ゼン、３−
又は４−メチルアミノ安息香酸、３−又は４−メチルア
ミノベンゼンスルホン酸、２−アミノナフタレン−１−
スルホン酸、４−アミノナフタレン−１−スルホン酸、
５−アミノナフタレン−１−スルホン酸、６−アミツナ
フタシン−１−スルホン酸、７−アミノナフタレン−
１−スルホン酸、８−アミノナフタレン−１−スルホン
酸、１−アミノナフタレン−２−スルホン酸、４−アミ
ノナフタレン−２−スルホン酸、５−アミノナフタレン
−２−スルホン酸、６−アミノナフタレン−２−スルホ
ン１７−アミノナフタレン−２−スルホン酸、７−メチ
ルアミノナフタレン−２−スルホン１７−二チルアミノ
ナフタレンー２−スルホン酸、７−プチルアミノナフタ
レンー２−スルホン酸、７−イソブチルアミノナフタレ
ン−２＝スルホン酸、８−アミノナフタレン−２−スル
ホン酸、４−アミノナフタレン−１，３−ジスルホン酸
、５−アミノナフタレン−１，３−ジスルホン酸、６−
アミノナフタレン−１，３−ジスルホン酸、７−アミノ
ナフタレン−１，３−ジスルホン酸、８−アミノナフタ
レン−１，３−ジスルホン酸、２−アミノナフタレン−
１，３−ジスルホン酸、３−アミノナフタレン−１，５
−ジスルホン酸、４−アミノナフタレン−１，５−ジス
ルホン酸、４−アミノナフタレン−１，６−ジスルホン
酸、８−アミノナフタレン−１，６−ジスルホン酸、４
−アミノナフタレン−１，７−ジスルホン酸、３−アミ
ノナフタレン−２，６−ジスルホン酸、４−アミノナフ
タレン−２，６−ジスルホン酸、３−アミノナフタレン
−２，７−ジスルホン酸、４−アミノナフタレン−２，
７−ジスルホン酸、６−アミノナフタレン−１，３，５
−）リスルホン酸、７−アミノナフタレン−１，３，５
−トリスルホン酸、４−アミノナフタレン−ｌ。In the general formula (I), when X is -NR2R3, HN used to form such a group
Examples of the compound represented by R2Rs include ammonia, I-aminobenzene, 1-amino-2-, -
3- or -4-methyl-benzene, 1-amino-3,4
- or -3,5-dimethylbenzene, l-amino-2-
, -3- or -4-ethylbenzene, 1-amino-2-
3- or -4-methoxybenzene, niamino-2--
3- or -4-ethoxybenzene, niamino-2--
3- or -4-chlorobenzene, 3- or 4-amino-
Phenylmethanesulfone L 2-13- or 4-aminobenzenesulfonic acid, 3-methylaminobenzenesulfonic acid, 3-dithylaminobenzenesulfonic acid, 4-methylaminobenzenesulfonic acid, 4-ethylaminobenzenesulfonic acid, 5 -aminobenzene-1,3-disulfonic acid, 6-aminobenzene-1,3-disulfonic acid,
6-aminobenzene-1,4-disulfonic acid, 4-aminobenzene-1,2-disulfonic acid, 4-amino-5-
Methylbenzene-12-disulfonic acid, 2-13- or 4-aminobenzoic acid, 5-aminobenzene-1,3-dicarboxylic acid, 5-amino-2-hydroxybenzenesulfonic acid, 4-amino-2-hydroxybenzene Sulfonic acid, 5-ami7-2-ethoxybenzenesulfonic acid, N
-methylaminobenzene, N-ethylaminobenzene,
1-methylamino-3- or -4-methylbenzene, 1
-ethylamino-4-chlorobenzene, 1-ethylamino-3-also 1! -4-methylbenzene, 1-(2-hydroxyethyl)-amino-3-methylbenzene, 3-
or 4-methylaminobenzoic acid, 3- or 4-methylaminobenzenesulfonic acid, 2-aminonaphthalene-1-
Sulfonic acid, 4-aminonaphthalene-1-sulfonic acid,
5-aminonaphthalene-1-sulfonic acid, 6-aminonaphthalene-1-sulfonic acid, 7-aminonaphthalene-
1-Sulfonic acid, 8-aminonaphthalene-1-sulfonic acid, 1-aminonaphthalene-2-sulfonic acid, 4-aminonaphthalene-2-sulfonic acid, 5-aminonaphthalene-2-sulfonic acid, 6-aminonaphthalene-2-sulfonic acid 2-Sulfone 17-aminonaphthalene-2-sulfonic acid, 7-methylaminonaphthalene-2-sulfone 17-ditylaminonaphthalene-2-sulfonic acid, 7-butylaminonaphthalene-2-sulfonic acid, 7-isobutylaminonaphthalene -2=sulfonic acid, 8-aminonaphthalene-2-sulfonic acid, 4-aminonaphthalene-1,3-disulfonic acid, 5-aminonaphthalene-1,3-disulfonic acid, 6-
Aminonaphthalene-1,3-disulfonic acid, 7-aminonaphthalene-1,3-disulfonic acid, 8-aminonaphthalene-1,3-disulfonic acid, 2-aminonaphthalene-1,3-disulfonic acid
1,3-disulfonic acid, 3-aminonaphthalene-1,5
-disulfonic acid, 4-aminonaphthalene-1,5-disulfonic acid, 4-aminonaphthalene-1,6-disulfonic acid, 8-aminonaphthalene-1,6-disulfonic acid, 4
-aminonaphthalene-1,7-disulfonic acid, 3-aminonaphthalene-2,6-disulfonic acid, 4-aminonaphthalene-2,6-disulfonic acid, 3-aminonaphthalene-2,7-disulfonic acid, 4-amino naphthalene-2,
7-disulfonic acid, 6-aminonaphthalene-1,3,5
-) Lysulfonic acid, 7-aminonaphthalene-1,3,5
-trisulfonic acid, 4-aminonaphthalene-l.
３、 ６−）ジスルホン酸、７−アミノナフタレン−１
，３，６−）ジスルホン酸、８−アミノナフタレン−１
，３，６−トリスルホン酸及び４−アミノナフタレン−
１，３，７−）ジスルホン酸の様な芳香族アミン、或い
はメチルアミン、エチルアミン、ｎ−プロピルアミン、
イソプロピルアミン、ｎ−ブチルアミン、イソブチルア
ミン、ＳｅＣ−ブチルアミン、ジメチルアミン、ジエチ
ルアミン、メチルエチルアミン、アリルアミン、２−ク
ロロエチルアミン、２−メトキシエチルアミン、２−ア
ミノエタノール、２−メチルアミノエタノール、ビス−
（２−ヒドロキシエチル〉アミン、２−アセチルアミノ
エチルアミン、１−アミノ−２−プロパツール、３−メ
トキシプロピルアミン、１−アミノ−３−ジメチルアミ
ノプロパン、２−アミノエタンスルホン酸、アミノメタ
ンスルホン酸、２−メチルアミノエタンスルホン酸、３
−アミノ−１−プロパンスルホン酸、２−スルファトエ
チルアミン、アミノ酢酸、メチルアミノ酢酸、ε−アミ
ノカプロン酸、ベンジルアミン、２−１３−もしくは４
−クロロベンジルアミン、４−メチルベンジルアミン、
Ｎ−メチルベンジルアミン、２−１３−もしくは４−ス
ルホベンジルアミン、２−フェニルエチルアミン、１−
フェニルエチルアミン、１−７エニルー２−プロピルア
ミンの様な脂肪族アミンを挙げることができる。3, 6-) disulfonic acid, 7-aminonaphthalene-1
,3,6-)disulfonic acid, 8-aminonaphthalene-1
, 3,6-trisulfonic acid and 4-aminonaphthalene-
Aromatic amines such as 1,3,7-)disulfonic acid, or methylamine, ethylamine, n-propylamine,
Isopropylamine, n-butylamine, isobutylamine, SeC-butylamine, dimethylamine, diethylamine, methylethylamine, allylamine, 2-chloroethylamine, 2-methoxyethylamine, 2-aminoethanol, 2-methylaminoethanol, bis-
(2-Hydroxyethyl> Amine, 2-acetylaminoethylamine, 1-amino-2-propatol, 3-methoxypropylamine, 1-amino-3-dimethylaminopropane, 2-aminoethanesulfonic acid, aminomethanesulfonic acid , 2-methylaminoethanesulfonic acid, 3
-Amino-1-propanesulfonic acid, 2-sulfatoethylamine, aminoacetic acid, methylaminoacetic acid, ε-aminocaproic acid, benzylamine, 2-13- or 4
-chlorobenzylamine, 4-methylbenzylamine,
N-methylbenzylamine, 2-13- or 4-sulfobenzylamine, 2-phenylethylamine, 1-
Mention may be made of aliphatic amines such as phenylethylamine, 1-7enyl-2-propylamine.
中でも特に好ましい、化合物としては、例えば、アニリ
ン、Ｎ−メチルアニリン、Ｎ−エチルアニリン、２−１
３−１たは４−クロロアニリン、Ｎ−メチル−２−−３
−または−４−クロロアニリン、Ｎ−エチル−２−−３
−または−４−クロロアニリン、２−１３−又は４−メ
チルアニリン、アニリン−２，４−又は−２，５−ジス
ルホン酸、３−または４−メチルアミノベンゼンスルホ
ン酸、３−または４−エチルアミノベンゼンスルホン酸
、２−．３−又は４−カルボキシアニリン、タウリン、
Ｎ−メチルタウリン、モノ−もしくはジ−エタノールア
ミン等を挙げることができる。Particularly preferred compounds include, for example, aniline, N-methylaniline, N-ethylaniline, 2-1
3-1 or 4-chloroaniline, N-methyl-2--3
-or-4-chloroaniline, N-ethyl-2--3
- or -4-chloroaniline, 2-13- or 4-methylaniline, aniline-2,4- or -2,5-disulfonic acid, 3- or 4-methylaminobenzenesulfonic acid, 3- or 4-ethyl Aminobenzenesulfonic acid, 2-. 3- or 4-carboxyaniline, taurine,
N-methyltaurine, mono- or di-ethanolamine, etc. can be mentioned.
Ｒ４及びＲ６で表される置換されていてもよいアルキル
としては、例えば１〜４個の炭素原子を有するアルコキ
シ、スルホ、カルボキシ、ヒドロキシ、クロロ、フェニ
ル、シアノ及びスルフアートの群から選ばれる、１又は
２個の置換基により置換されていてもよい炭素原子１〜
４個を有するアルキルが好ましい。The optionally substituted alkyl represented by R4 and R6 is selected from the group consisting of alkoxy, sulfo, carboxy, hydroxy, chloro, phenyl, cyano and sulfate having 1 to 4 carbon atoms, 1 to carbon atoms optionally substituted with 2 substituents
Alkyl having 4 is preferred.
中でも好ましくは、メチル、エチル、ｎ−プロピル、１
ｓｏ−プロピル、ｎ−ブチル、１ｓｏ−ブチル、５ｅｃ
−ブチル、β−ヒドロキシエチル、β−スルフアートエ
チル、β−スルホエチル、β−メトキシエチル、β−エ
トキシエチル、β−クロロエチル及びβ−カルボキシエ
チル等が挙げられる。Among them, methyl, ethyl, n-propyl, 1
so-propyl, n-butyl, 1so-butyl, 5ec
-butyl, β-hydroxyethyl, β-sulfatoethyl, β-sulfoethyl, β-methoxyethyl, β-ethoxyethyl, β-chloroethyl, β-carboxyethyl, and the like.
又％ Ｒ４及びＲｓで表される置換されていてもよいフ
ェニルとしては、例えば、１〜４個の炭素原子を有する
アルキル、１〜４個の炭素原子を有するアルコキシ、ス
ルホ、カルボキシ、クロロ及びプロその群から選ばれる
、１又は２個の置換基により置換されていてもよいフェ
ニルが好ましい。Furthermore, the optionally substituted phenyl represented by %R4 and Rs includes, for example, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, sulfo, carboxy, chloro, and propoxy. Preferred is phenyl optionally substituted with one or two substituents selected from the group.
中でも特に好ましくは、フェニル、２−１３−又は４−
スルホフェニル、２，４−又は２，５−ジスルホフェニ
ル、２−１３−又は４−クロロフェニル、２−１３−又
は４−メチルフェニル、及び２−１３−又は４−メトキ
シフェニル等が挙げられる。Among them, phenyl, 2-13- or 4-
Examples include sulfophenyl, 2,4- or 2,5-disulfophenyl, 2-13- or 4-chlorophenyl, 2-13- or 4-methylphenyl, and 2-13- or 4-methoxyphenyl.
又、Ｒ１及びＲｓで表される置換されていてもよいナフ
チルとしては、例えば、ヒドロキシ、カルボキシ、スル
ホ、１〜４個の炭素原子を有するアルキル、１〜４個の
炭素原子を有するアルコキシ及びクロロの群から選ばれ
る、工、２又は３個の置換基により置換されていてもよ
いナフチルが好ましい。Further, the optionally substituted naphthyl represented by R1 and Rs includes, for example, hydroxy, carboxy, sulfo, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, and chloro. Naphthyl optionally substituted with 2 or 3 substituents is preferred.
中でも特に好ましくは、２−１３−１４−１５．６−１
７−又は８−スルホ−１−ナフチル、１−１５−１６−
１７−又は８−スルホ−２−ナフチル、１．５−１５．
７−１６．８−１４，８．４．７−１３，８−１４，６
−１３，７−又は３，６−ジスルホ−２−ナフチル、４
． ６． ８．２． ４． ７＝又は３． ６． ８−
）リス用ホー１−ナフチル、１．５．７−１４，６，８
−又は３、 ６． ８−）ジスルホ−２−ナフチル等が
挙げられる。Among them, particularly preferred is 2-13-14-15.6-1
7- or 8-sulfo-1-naphthyl, 1-15-16-
17- or 8-sulfo-2-naphthyl, 1.5-15.
7-16.8-14, 8.4.7-13, 8-14, 6
-13,7- or 3,6-disulfo-2-naphthyl, 4
．． 6. 8.2. 4. 7=or 3. 6. 8-
) Ho 1-naphthyl for squirrels, 1.5.7-14,6,8
- or 3, 6. 8-) Disulfo-2-naphthyl and the like.
又、Ｒ１及びＲ５で表される置換されていてもよいベン
ジルとしては、例えば、１〜４個の炭素原子を有するア
ルキル、１〜４個の炭素原子を有するアルコキシ、スル
ホ及びクロロの群から選ばれる、１又は２個の置換基に
より置換さていてもよいベンジルが好ましい。Furthermore, the optionally substituted benzyl represented by R1 and R5 is selected from the group of, for example, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, sulfo, and chloro. Benzyl optionally substituted with one or two substituents is preferred.
中でも特に好ましくは、ベンジル、２−１３−又は４−
スルホベンジル等があげられる。Among these, benzyl, 2-13- or 4-
Examples include sulfobenzyl.
前記一般式（１）において、Ｘが−○Ｒ２であるとき、
そのような基を懲戒するために用いられる、Ｒ４０Ｈで
示される化合物としては、例えば、フェノーノペ １−
ヒドロキシ−２−−３−又は−４−メチルベンゼン、１
−ヒドロキシ−３゜４−又Ｉ！−３，５−ジメチルベン
ゼン、１−ヒドロキシ−２−、−３−又は−４−エチル
ベンゼン、１−ヒドロキシ−２−−３−又は−４−メト
キシベンゼン、１−ヒドロキシ−２−、−３−又は−４
−エトキシベンゼン、ｌ−ヒドロキシ−２−３−又１ｔ
−４−クロルベンゼン、３−又は４−ヒドロキシ−フェ
ニルメタンスルホン酸、３−ヒドロキシベンゼンスルホ
ン酸、４−とドロキシベンゼンスルホン酸、５−ヒドロ
キシベンゼン−１，３−ジスルホン酸、６−ヒトロキシ
ベンゼンー１．４−ジスルホン酸、４−ヒドロキシベン
ゼン−１，２−ジスルホン酸、４−ヒドロキシ−５−メ
チルベンゼン−１，２−ジスルホン酸、３−又は４−ヒ
ドロキシ安息香酸、５−ヒドロキシベンゼン−１，３−
ジカルボン酸、５−ヒドロキシ−２−エトキシベンゼン
スルホン［２−ヒドロキシナフタレン−１−スルホン酸
、４−ヒドロキシナフタレン−１−スルホン酸、５−ヒ
ドロキシナフタレン−ニースルホン酸、６−ヒトロキシ
ナフタレンー１−スルホン酸、７−ヒトロキシナフタレ
ンー１−スルホン酸、８−ヒドロキシナフタレン−１−
スルホン酸、１−ヒドロキシナフタレン−２−スルホン
酸、４−ヒドロキシナフタレン−２−スルホン１５−ヒ
ドロキシナフタレン−２−スルホン酸、６−ヒトロキシ
ナフタレンー２−スルホン酸、７−ヒトロキシナフタレ
ンー２−スルホン酸、８−ヒドロキシナフタレン−２−
スルホン酸、４−ヒドロキシナフタレン−１，３−ジス
ルホン酸、５−ヒドロキシナフタレン−１３−ジスルホ
ン酸、６−ヒトロキシナフタレンー１．３−ジスルホン
酸、７−ヒトロキシナフタレンー１．３−ジスルホン酸
、８−ヒドロキシナフタレン−１，３−ジスルホンｉ１
２．２−ヒドロキシナフタレン−１，５−ジスルホン酸
、３−ヒト９キシナフタレン−１，５−ジスルホン酸、
４−ヒドロキシナフタレン−１，５−ジスルホン酸、４
−ヒドロキシナフタレン−１，６−ジスルホン１８−ヒ
ドロキシナフタレン−１，６−ジスルホン酸、４−ヒド
ロキシナフタレン−１，７−ジスルホン酸、３−ヒドロ
キシナフタレン−２，６−ジスルホン酸、４−ヒドロキ
シナフタレン−２６−ジスルホン酸、３−ヒドロキシナ
フタレン−２，７−ジスルホン酸、４−ヒドロキシナフ
タレン−２，７−ジスルホン酸、６−ヒトロキシナフタ
レンー１．３．５−）ジスルホン酸、７−ヒトロキシナ
フタレンー１．３．５−）ジスルホン酸、４−ヒドロキ
シナフタレン−１，３，６−）ジスルホン酸、７−アミ
ノナフタレン−１，３゜６−トリスルホン酸、８−アミ
ノナフタレン−１３，６−）ジスルホン酸及び４−アミ
ノナフタレン−１，３，７−）ジスルホン酸の様な芳香
族化合物、或いはメタノール、エタノール、ｎ−プロパ
ツール、インプロパツール、ｎ−ブタノール、インブタ
ノール、５ｅＣ−ブタノーノベ２−りロロエタノール、
２−メトキシエタノール、２エトキシエタノール、３−
メトキシプロパツール、３−エトキシプロパノール、２
−ヒドロキシェタンスルホン酸、３−ヒドキシ−１−プ
ロパンスルホン酸、２−シアノエタノール、２−スルフ
アートエタノール、グリコール酸、３−ヒドロキシプロ
ピオン酸、ベンジルアルコール、２−．３−もしくは４
−クロロベンジルアルコール、４−メチルベンジルアル
コーノベ２−，３−もＬ＜Ｉｆ４−スルホベンジルアル
コール、２−フェニルエタノール、１−フェニル−２−
プロパツールの様な脂肪族化合物、及び前記一般式（Ｉ
）において、Ｘが一３Ｒｓであるとき、そのような基を
懲戒するために用いられる、Ｒ，ＳＨとしては、上記化
合物のヒドロキシがメルカプトである化合物をあげるこ
とができる。In the general formula (1), when X is -○R2,
Compounds represented by R40H used to discipline such groups include, for example, phenonope 1-
Hydroxy-2--3- or -4-methylbenzene, 1
-Hydroxy-3゜4-MataI! -3,5-dimethylbenzene, 1-hydroxy-2-, -3- or -4-ethylbenzene, 1-hydroxy-2--3- or -4-methoxybenzene, 1-hydroxy-2-, -3- or -4
-ethoxybenzene, l-hydroxy-2-3-also 1t
-4-chlorobenzene, 3- or 4-hydroxy-phenylmethanesulfonic acid, 3-hydroxybenzenesulfonic acid, 4- and droxybenzenesulfonic acid, 5-hydroxybenzene-1,3-disulfonic acid, 6-hydroxybenzene Benzene-1,4-disulfonic acid, 4-hydroxybenzene-1,2-disulfonic acid, 4-hydroxy-5-methylbenzene-1,2-disulfonic acid, 3- or 4-hydroxybenzoic acid, 5-hydroxybenzene -1,3-
Dicarboxylic acid, 5-hydroxy-2-ethoxybenzenesulfone [2-hydroxynaphthalene-1-sulfonic acid, 4-hydroxynaphthalene-1-sulfonic acid, 5-hydroxynaphthalene-neesulfonic acid, 6-hydroxynaphthalene-1-sulfone acid, 7-hydroxynaphthalene-1-sulfonic acid, 8-hydroxynaphthalene-1-
Sulfonic acid, 1-hydroxynaphthalene-2-sulfonic acid, 4-hydroxynaphthalene-2-sulfone 15-hydroxynaphthalene-2-sulfonic acid, 6-hydroxynaphthalene-2-sulfonic acid, 7-hydroxynaphthalene-2- Sulfonic acid, 8-hydroxynaphthalene-2-
Sulfonic acid, 4-hydroxynaphthalene-1,3-disulfonic acid, 5-hydroxynaphthalene-13-disulfonic acid, 6-hydroxynaphthalene-1,3-disulfonic acid, 7-hydroxynaphthalene-1,3-disulfonic acid , 8-hydroxynaphthalene-1,3-disulfone i1
2.2-hydroxynaphthalene-1,5-disulfonic acid, 3-human 9xinaphthalene-1,5-disulfonic acid,
4-hydroxynaphthalene-1,5-disulfonic acid, 4
-Hydroxynaphthalene-1,6-disulfone 18-hydroxynaphthalene-1,6-disulfonic acid, 4-hydroxynaphthalene-1,7-disulfonic acid, 3-hydroxynaphthalene-2,6-disulfonic acid, 4-hydroxynaphthalene- 26-disulfonic acid, 3-hydroxynaphthalene-2,7-disulfonic acid, 4-hydroxynaphthalene-2,7-disulfonic acid, 6-hydroxynaphthalene-1.3.5-)disulfonic acid, 7-hydroxynaphthalene-2,7-disulfonic acid -1.3.5-)disulfonic acid, 4-hydroxynaphthalene-1,3,6-)disulfonic acid, 7-aminonaphthalene-1,3゜6-trisulfonic acid, 8-aminonaphthalene-13,6- ) disulfonic acid and 4-aminonaphthalene-1,3,7-)disulfonic acid, or methanol, ethanol, n-propatol, impropatol, n-butanol, imbutanol, 5eC-butanobe2 -Riroroethanol,
2-methoxyethanol, 2-ethoxyethanol, 3-
Methoxypropanol, 3-ethoxypropanol, 2
-Hydroxyethanesulfonic acid, 3-hydroxy-1-propanesulfonic acid, 2-cyanoethanol, 2-sulfatoethanol, glycolic acid, 3-hydroxypropionic acid, benzyl alcohol, 2-. 3- or 4
-chlorobenzyl alcohol, 4-methylbenzyl alcohol, 2-, 3- also L<If4-sulfobenzyl alcohol, 2-phenylethanol, 1-phenyl-2-
Aliphatic compounds such as propatool, and the general formula (I
), when X is 13Rs, examples of R and SH used to discipline such a group include compounds in which the hydroxy of the above compound is mercapto.
Ｒ３で表される低級アルキル基としては、メチル基、エ
チル基およびプロピル基が例示され、特にメチル基が好
ましい。Examples of the lower alkyl group represented by R3 include a methyl group, an ethyl group, and a propyl group, with a methyl group being particularly preferred.
Ｗで表されるアルキレン基は、（ＣＨ２）ｇ（式中、ｌ
は１〜６を表す。〉で示され、これらの中、特に、ｌ＝
２または３のものが好ましい。The alkylene group represented by W is (CH2)g (in the formula, l
represents 1 to 6. 〉, among these, especially l=
2 or 3 are preferred.
Ｙが置換基を有するピリジニオ基である場合の置換基と
しては、カルボキシ、カルバモイル、スルホ、ハロゲノ
および置換もしくは無置換の１〜４個の炭素原子を有す
るアルキルが挙げられる。When Y is a pyridinio group having a substituent, examples of the substituent include carboxy, carbamoyl, sulfo, halogeno, and substituted or unsubstituted alkyl having 1 to 4 carbon atoms.
置換アルキル基としてはβ−ヒドロキシエチル、β−ス
ルホエチルなどが例示される。Ｙで表されるピリジニオ
基としては、カルボキシまたはカルバモイル置換ピリジ
ニオ基が好ましく、中でもカルボキシピリジニオ基が染
料特性上好適である。Examples of substituted alkyl groups include β-hydroxyethyl and β-sulfoethyl. The pyridinio group represented by Y is preferably a carboxy- or carbamoyl-substituted pyridinio group, and a carboxypyridinio group is especially preferred from the viewpoint of dye properties.
置換基を有していてもよいピリジンとして好ましくは、
ピリジン、２−．３−又は４−カルボキシピリジン、２
−．３−又は４−カルバモイルピリジン、３−スルホピ
リジン、４−β−スルホエチルピリジン、３−β−ヒド
ロキシエチルピリジン、４−クロロピリジン、３−メチ
ルビリジン、３．５−ジカルボキシピリジン等が挙げら
れる。Preferably, pyridine which may have a substituent is
Pyridine, 2-. 3- or 4-carboxypyridine, 2
−． Examples include 3- or 4-carbamoylpyridine, 3-sulfopyridine, 4-β-sulfoethylpyridine, 3-β-hydroxyethylpyridine, 4-chloropyridine, 3-methylpyridine, 3,5-dicarboxypyridine, etc. .
中でも特に好ましくは３−１又は４−カルボキシピリジ
ンにコチン酸、イソニコチン酸〉である。Among these, particularly preferred are 3-1 or 4-carboxypyridine, cotinic acid, and isonicotinic acid.
本発明化合物は遊離酸の形でまた（よその塩の形で存在
し、特にアルカリ金属塩およびアルカリ類金属塩、中で
もソーダ塩、カリ塩、リチウム塩が好ましい。The compounds of the invention exist in the form of free acids and also in the form of salts, in particular alkali metal and alkali metal salts, especially the soda, potassium and lithium salts.
本発明化合物は、例えば次の様にして製造することがで
きる。下記一般式（Ｉｆ）
〔式中、Ｄ，Ｗ，Ｒ．、Ｉ’ｈ，Ｒ．、及びＺ，１ま前
言己の意味を有する。］
で示される化合物と、下記一般式（ＩＩＩ）〜（Ｖｌ）
Ｒ。The compound of the present invention can be produced, for example, in the following manner. The following general formula (If) [wherein D, W, R. , I'h, R. , and Z,1 have the same meaning as before. ] Compounds represented by the following general formulas (III) to (Vl)
R.
Ｈ Ｎ Ｒ ２Ｒ ｓ （ ｒＶ ）ＨｏＲ．
（Ｖ）
Ｈ Ｓ Ｒ１ （ＶＩ）
（式中、Ａ％Ｒ １．Ｒ２，Ｒ３． Ｒ４，Ｒｓ前記の
意味を有する。）
及びＺ２は
で示される化合物のいずれかとを、２．４．６−トリハ
ロゲノ−Ｓ−トリアジンに任意の順序で縮合させること
により、下記一般式（■〉〔式中、Ｔはハロゲンを表し
、ＤＳＷＳＲｅ，Ｒ７、ＲＬ及びＺｌは前記の意味を有
する。〕で示される化合物を得た後、ピリジン化合物を
縮合させることによって、゛−一般式Ｉ）の化合物を得
ることができる。H N R 2R s (rV)HoR.
(V) H S R1 (VI) (In the formula, A%R 1.R2, R3. R4, Rs have the above meanings.) and Z2 are any of the compounds represented by 2.4.6- By condensation with trihalogeno-S-triazine in any order, a compound represented by the following general formula (■) [wherein T represents a halogen and DSWSRe, R7, RL and Zl have the above meanings] After obtaining, a compound of general formula I) can be obtained by condensing a pyridine compound.
２、４．６−）リハロゲノーｓ−）リアジンとの縮合反
応においてはその順序は特に制限されるものではなく、
また反応条件も特に制限されないが、−次的には温度−
１０℃乃至４０℃でｐＨ２乃至９、二次的には温度０乃
至７０℃でｐＨ２乃至９、更に三次的には温度１０乃至
１００℃でｐＨ２乃至７に調整しながら縮合させて一般
式（■）で示される化合物又はその塩を得ることができ
る。In the condensation reaction with 2,4.6-)rehalogenose-)lyazine, the order is not particularly limited,
Also, the reaction conditions are not particularly limited, but - secondly, temperature -
Condensation is carried out while adjusting the pH to 2 to 9 at 10 to 40 degrees Celsius, secondarily to pH 2 to 9 at 0 to 70 degrees Celsius, and tertiary to pH 2 to 7 at 10 to 100 degrees Celsius to obtain the general formula (■ ) or a salt thereof can be obtained.
原料の２．４．６−）ジハロゲノ−８−トリアジンとし
ては、特に塩化シアヌルとフッ化シアヌルが好ましい。As the raw material 2.4.6-)dihalogeno-8-triazine, cyanuric chloride and cyanuric fluoride are particularly preferred.
本発明化合物は、繊維反応性を有し、ヒドロキシ基含有
またはカルボンアミド基含有材料の染色又は捺染に使用
できる。材料は繊維材料の形で、あるいはその混紡材料
の形で使用されるのが好ましい。The compound of the present invention has fiber reactivity and can be used for dyeing or printing hydroxy group-containing or carbonamide group-containing materials. Preferably, the material is used in the form of a fibrous material or a blend thereof.
ヒドロキシ基含有材料は天然又は合成ヒドロキシ基含有
材料、たとえばセルロース繊維材料又はその再生生成物
及びポリビニルアルコールである。Hydroxy group-containing materials are natural or synthetic hydroxy group-containing materials, such as cellulose fiber materials or their regenerated products and polyvinyl alcohol.
セルロース繊維材料は木綿、しかもその他の植物繊維、
たとえばリネン、麻、ジュート及びラミー繊維が好まし
い。再生セルロース繊維はたとえばビスコース・ステー
ブル及びフィラメントビスコースである。Cellulose fiber material is cotton, as well as other vegetable fibers,
For example, linen, hemp, jute and ramie fibers are preferred. Regenerated cellulose fibers are, for example, viscose stable and filament viscose.
カルボンアミド基含有材料はたとえば合成及び天然のポ
リアミド及びポリウレタン、特に繊維の形で、たとえば
羊毛及びその他の動物毛、絹、皮革、ポリアミド−６，
６、ポリアミド−６、ポリアミド−１１及びポリアミド
−４である。Materials containing carbonamide groups are, for example, synthetic and natural polyamides and polyurethanes, especially in the form of fibers, such as wool and other animal hairs, silk, leather, polyamide-6,
6, polyamide-6, polyamide-11 and polyamide-4.
本発明化合物は、上述の材料上に、特に上述の繊維材料
上に、物理的化学的性状に応じた方法で、染色又は捺染
できる。The compounds of the present invention can be dyed or printed on the above-mentioned materials, in particular on the above-mentioned fiber materials, in a manner depending on their physical and chemical properties.
例えば、セルロース繊維上に吸尽染色する場合、炭酸ソ
ーダ、第三燐酸ソーダ、苛性ソーダ等の酸結合剤の存在
下、場合により中性塩、例えば芒硝又は食塩を加え、所
望によっては、溶解助剤、浸透剤又は均染剤を併用し、
比較的低い温度で行われる。染料の吸尽を促進する中性
塩は、本来の染色温度に達した後に初めて又はそれ以前
に、場合によっては分割して添加できる。For example, in the case of exhaust dyeing on cellulose fibers, in the presence of an acid binder such as soda carbonate, sodium phosphate or caustic soda, a neutral salt such as mirabilite or common salt is optionally added, and if desired, a solubilizer is added. , use a penetrant or leveling agent together,
It is carried out at relatively low temperatures. The neutral salts which accelerate the exhaustion of the dyestuff can be added only after the actual dyeing temperature has been reached, or even before then, optionally in portions.
バジング法に従ってセルロース繊維を染色する場合、室
温又は高められた温度でパッドし乾燥後、スチーミング
又は乾熱によって固着できる。When dyeing cellulose fibers according to the bazing method, it can be padded at room temperature or at an elevated temperature, dried and then fixed by steaming or dry heat.
セルロース繊維に対して捺染を行う場合、−相で、例え
ば重曹又はその他の酸縮合剤を含有する捺染ペーストで
捺染し、次いで１００〜１６０℃でスチーミングするこ
とによって、あるいは二相で、例えば中性又は弱酸性捺
染ペーストで捺染し、これを熱い電解質含有アルカリ性
基に通過させ、又はアルカリ性電解質含有バジング液で
オーバーバジングし、スチーミング又は乾熱処理して実
施できる。When printing is carried out on cellulose fibers, it can be printed in one phase, e.g. with a printing paste containing baking soda or other acid condensing agents, and then steamed at 100-160°C, or in two phases, e.g. This can be carried out by printing with an acidic or weakly acidic printing paste, passing it through a hot electrolyte-containing alkaline group, or by overbagging with an alkaline electrolyte-containing bagging liquid and by steaming or dry heat treatment.
捺染ペーストには、例えばアルギン酸ソーダ又は澱粉エ
ーテルのような糊剤又は乳化剤が、所望によっては、例
えば尿素のような通常の捺染助剤かつく又は）分散剤と
併用して用いられる。Thickening agents or emulsifiers, such as, for example, sodium alginate or starch ethers, are used in the printing pastes, if desired in combination with customary printing auxiliaries and/or dispersants, such as, for example, urea.
セルロース繊維上に本発明化合物を固定させるに適した
酸結合剤は、例えばアルカリ金属又はアルカリ土類金属
と無機又は有機酸あるいは加熱状態でアルカリ遊離する
化合物との水溶性塩基性塩である。特にアルカリ金属の
水酸化物及び弱ないし中程度の強さの無機又は有機酸の
アルカリ金属塩が挙げられ、その内、特にソーダ塩及び
カリ塩が好ましい。このような酸結合剤として、例えば
苛性ソーダ、苛性カリ、重曹、炭酸ソーダ、蟻酸ソーダ
、炭酸カリ、第一、第二又は第三燐酸ソーダ、ケイ酸ソ
ーダ、トリクロロ酢酸ソーダ等が挙げられる。Acid binders suitable for immobilizing the compounds of the invention on cellulose fibers are, for example, water-soluble basic salts of alkali metals or alkaline earth metals with inorganic or organic acids or compounds which liberate alkali upon heating. Particular mention may be made of alkali metal hydroxides and alkali metal salts of weak to medium strength inorganic or organic acids, of which soda salts and potassium salts are particularly preferred. Examples of such acid binders include caustic soda, caustic potash, sodium bicarbonate, sodium carbonate, sodium formate, potassium carbonate, primary, secondary, or tertiary sodium phosphate, sodium silicate, sodium trichloroacetate, and the like.
台底及び天然のポリアミド及びポリウレタン繊維の染色
は、まず酸性ないし弱酸性の染浴からｐＨ値の制御下に
吸尽させ、次に固着させるため中性、場合によりアルカ
リ性のｐＨ値に変化させることによって行える。染色は
通常６０〜１２０℃の温度で行えるが、均染性を達成す
るために通常の均染剤、例えば塩化シアヌルと３倍モル
のアミノベンゼンスルホン酸又はアミノナフタレンスル
ホン酸との縮合生成物あるいは例えばステアリルアミン
とエチレンオキサイドとの付加生成物を用いることもで
きる。The dyeing of base and natural polyamide and polyurethane fibers is first carried out under pH control from an acidic or slightly acidic dye bath, and then changed to a neutral or even alkaline pH value for fixation. This can be done by Dyeing can usually be carried out at a temperature of 60 to 120°C, but in order to achieve level dyeing properties, conventional leveling agents such as a condensation product of cyanuric chloride and 3 times the mole of aminobenzenesulfonic acid or aminonaphthalenesulfonic acid or For example, addition products of stearylamine and ethylene oxide can also be used.
本発明化合物は繊維材料に対する染色及び捺染において
優れた性能を発揮する点に特徴がある。The compound of the present invention is characterized in that it exhibits excellent performance in dyeing and printing textile materials.
特にセルロース繊維材料の染色に好適であり、良好な耐
光性と耐汗日光性、優れた耐湿潤性、たとえば耐洗濯性
、耐過酸化洗濯性、耐塩素性、耐汗性、耐酸加水分解性
及び耐アルカリ性、更に良好な耐摩擦性と耐アイロン性
を有する。Especially suitable for dyeing cellulose fiber materials, good light fastness and sweat resistance, good moisture resistance, such as washing resistance, peroxidation washing resistance, chlorine resistance, sweat resistance, acid hydrolysis resistance and alkali resistance, as well as good abrasion resistance and ironing resistance.
また優れたビルドアツプ性、均染性及びウオツシュオフ
性、さらに良好な溶解性と吸尽・固着性を有する点、染
色温度や染浴比の変動による影響を受けにくく安定した
品質の染色物が得られる点において特徴を有する。In addition, it has excellent build-up properties, level dyeing properties, and wash-off properties, as well as good solubility, exhaustion and fixation properties, and is less susceptible to fluctuations in dyeing temperature and dye bath ratio, resulting in dyed products of stable quality. It has characteristics in certain points.
また、得られた染色物のフィックス処理時や樹脂加工時
における変色が少なく、保存時の塩基性物質との接触に
よる変化が少ないことも特徴である。Another characteristic of the dyed product is that there is little discoloration during fix treatment or resin processing, and there is little change due to contact with basic substances during storage.
以下、実施例により本発明の詳細な説明する。Hereinafter, the present invention will be explained in detail with reference to Examples.
例中、部および％は夫々重量部および重量％を表す。In the examples, parts and % represent parts by weight and % by weight, respectively.
（以下余白）
実施例１
１−（β−アミノエチル）−４−メチル−６−ヒドロキ
シ−２−ピリドン３．４部をアニリン−２゜５−ジスル
ホン酸５．１部と塩化シアヌル３．７１を反応すること
で得られた縮合物を含む水溶ｔＬ２００部に加え、ｐＨ
７〜９．１０〜３０℃で反応が終了するまで撹拌した。(Left below) Example 1 3.4 parts of 1-(β-aminoethyl)-4-methyl-6-hydroxy-2-pyridone, 5.1 parts of aniline-2°5-disulfonic acid and 3.71 parts of cyanuric chloride Add to 200 parts of an aqueous solution containing the condensate obtained by reacting the
7-9. Stirred at 10-30°C until the reaction was completed.
この反応液に、２−アミノ−１−スルホナフタレン−６
−β−スルフアートエチルスルホン８．２部を通常の方
法でジアゾ化した水溶液１００部を、ｐＨ５〜７に調整
しながら、０〜２０℃で加え、同温度、同ｐＨでカップ
リングが終了するまで撹拌した。反応終了後、ニコチン
酸３．０部を加え、ｐＨ２〜４．６０〜８０℃で反応が
終了するまで撹拌することによって、遊離酸の形で、下
記構造式のピリドンモノアゾ化合物を得た。Add 2-amino-1-sulfonaphthalene-6 to this reaction solution.
-100 parts of an aqueous solution prepared by diazotizing 8.2 parts of β-sulfatoethyl sulfone in a conventional manner is added at 0 to 20°C while adjusting the pH to 5 to 7, and the coupling is completed at the same temperature and pH. Stir until After the reaction was completed, 3.0 parts of nicotinic acid was added and stirred at pH 2 to 4.60 to 80°C until the reaction was completed to obtain a pyridone monoazo compound having the following structural formula in the form of a free acid.
（以下余白）
実施例２
実施例１において使用した１−（β−アミノエチル）−
４−メチル−６−ヒドロキシ−２−ピリドンの代わりに
第２欄のピリドン化合物を、２−アミノ−１−スルホナ
フタレン−６−β−スルフアートエチルスルホンの代わ
りに、第３欄のアミンをそれぞれ等モル用いて、実施例
１と同様の方法で行う事によって、対応するピリドンモ
ノアゾ化合物を得た。(Left below) Example 2 1-(β-aminoethyl)- used in Example 1
4-Methyl-6-hydroxy-2-pyridone is replaced by the pyridone compound in the second column, and 2-amino-1-sulfonaphthalene-6-β-sulfatoethylsulfone is replaced by the amine in the third column. The corresponding pyridone monoazo compound was obtained by carrying out the same method as in Example 1 using equimolar amounts of each.
（以下余白〉
実施例３
実施例１および２で使用゛した、アニリン−２゜５−ジ
スルホン酸の代わりに、以下に示す化合物の等モルを用
いて、実施例１と同様の方法で行う事によって、対応す
るピリドンモノアゾ化合物を得た。(Left below) Example 3 In place of the aniline-25-disulfonic acid used in Examples 1 and 2, the procedure was carried out in the same manner as in Example 1, using equimolar amounts of the compounds shown below. The corresponding pyridone monoazo compound was obtained.
（１）オルタニル酸
０〕メタニル酸
（３）スルファニル酸
（４）１−アミノナフタレン−３，６−ジスルホン酸（
５）１−アミノナフタレン−４，６，８−）ジスルホン
酸
（６）２−アミノナフタレン−１，５−ジスルホン酸（
７）２−アミノナフタレン−４，８−ジスルホン酸（８
）２−アミノナフタレン−３，６，８−）ジスルホン酸
（９）２−アミノナフタレン−４，６，８−トリスルホ
ン酸
００アニリン−２，４−ジスルホン酸
ＯＤアニリン
（Ｌ１５Ｎ−メチルアニリン
０３１Ｎ−二チルアニリン
α４）ｍ−トルイジン
α５１１）−トルイジン
Ｑｅｍ−クロルアニリン
Ｑ？） ｐ−アニンジン
０Φｐ−アミノ安息香酸
（至）アンモニア
（至）エチルアミン
（２１）β−ヒドロキシエチルアミン
（２２〉β−アラニン
（２３〉タウリン
（２４） Ｎ−メチルタウリン
（２５） ｏ−アミノ安息香酸
（２６） ｐ−クロルアニリン
（２８）
（２９〉
３Ｕ２し２ＰＬ４Ｕろｕｎｌ′１
（３８）
（４０）
（４２）ＨＪ−（ＣＨｚ）ＪＣ２Ｈ４ＳＯａＣＪｓ ｃ
ｐ（４３） ＨＪ−（ＣＨ２）２ＤＣ２Ｈ１ＳＯ２
Ｃ）ｌ：ｃＨａ（４４） ）ＩＪ−（Ｃ）１．）、０
Ｃ２）１４ＳＯ２ＣＨ＝ＣＨ２実施例４
実施例１〜３で使用したニコチン酸の代わりに、下記の
ピリジン化合物を用いることによって、対応するピリド
ンモノアゾ化合物を得た。(1) Ortanilic acid 0] methanic acid (3) Sulfanilic acid (4) 1-aminonaphthalene-3,6-disulfonic acid (
5) 1-aminonaphthalene-4,6,8-)disulfonic acid (6) 2-aminonaphthalene-1,5-disulfonic acid (
7) 2-aminonaphthalene-4,8-disulfonic acid (8
) 2-aminonaphthalene-3,6,8-)disulfonic acid (9) 2-aminonaphthalene-4,6,8-trisulfonic acid 00 Aniline-2,4-disulfonic acid OD Aniline (L15N-methylaniline 031N- Dithylaniline α4) m-Toluidine α511)-Toluidine Qem-Chloraniline Q? ) p-Aningine0Φp-Aminobenzoic acid (to) Ammonia (to) Ethylamine (21) β-Hydroxyethylamine (22> β-alanine (23> Taurine (24) N-Methyltaurine (25) o-Aminobenzoic acid ( 26) p-Chloraniline (28) (29> 3U2 and 2PL4Uunl'1 (38) (40) (42)HJ-(CHz)JC2H4SOaCJs c
p(43) HJ-(CH2)2DC2H1SO2
C)l:cHa(44))IJ-(C)1. ), 0
C2) 14SO2CH=CH2 Example 4 The corresponding pyridone monoazo compound was obtained by using the following pyridine compound in place of the nicotinic acid used in Examples 1 to 3.
（１）
実施例５
実施例１で用いた、アニリン−２，５−ジスルホン酸と
塩化シアヌルの縮合物の代わりに、等モルの２−メトキ
シ−４，６−ジクロロ−５−）リアジンを用いて、実施
例１と同様の方法で操作することによって、下記構造式
のピリドンモノアゾ化合物を得た。(1) Example 5 Instead of the condensate of aniline-2,5-disulfonic acid and cyanuric chloride used in Example 1, equimolar amount of 2-methoxy-4,6-dichloro-5-) riazine was used. By operating in the same manner as in Example 1, a pyridone monoazo compound having the following structural formula was obtained.
実施例６
実施例５で用いた２−メトキシ−４，６−ジクロロ−５
−）リアジンの代わりに、以下の化合物を用いることに
よって、対応するピリドンモノアゾ化合物を得た。Example 6 2-methoxy-4,6-dichloro-5 used in Example 5
-) The corresponding pyridone monoazo compound was obtained by using the following compound instead of riazine.
実施例７
実施例５および６において使用した１−（β−アミノエ
チル）−４−メチル−６−ヒドロキシ−２−ピリドンお
よび２−アミノ−１−スルホナフタレン−６−β−スル
フアートエチルスルホンの代わりに、実施例２の表中の
第２欄のピリドン化合物および第３欄のアミンをそれぞ
れ用いて、実施例５と同様の方法で行う事によって、対
応するピリドンモノアゾ化合物を得た。Example 7 1-(β-aminoethyl)-4-methyl-6-hydroxy-2-pyridone and 2-amino-1-sulfonaphthalene-6-β-sulfatoethylsulfone used in Examples 5 and 6 The corresponding pyridone monoazo compound was obtained by carrying out the same method as in Example 5, using the pyridone compound in the second column and the amine in the third column in the table of Example 2 instead.
実施例８
実施例１〜７に記載の各々のピリドンモノアゾ化合物０
．１．０．３及び０．６部を各々水２００部に溶解し、
芒硝１０部と木綿１０部を加え、６０℃に昇温し炭酸ソ
ーダ４部を加えて１時間染色した。Example 8 Each pyridone monoazo compound described in Examples 1 to 7 0
．． 1.0.3 and 0.6 parts were each dissolved in 200 parts of water,
10 parts of Glauber's salt and 10 parts of cotton were added, the temperature was raised to 60°C, 4 parts of soda carbonate was added, and dyeing was carried out for 1 hour.
水洗、ソーピング、水洗そして乾燥を行い、諸堅牢度に
優れ、良好なビルドアツプ性を有する黄色の染色物が得
られた。After washing with water, soaping, washing with water and drying, a yellow dyed product with excellent fastness and good build-up properties was obtained.
実施例９
実施例１〜７に記載の各々のピリドンモノアゾ化合物の
それぞれを用いて、以下の組成をもつ色糊を作った。Example 9 A colored paste having the following composition was made using each of the pyridone monoazo compounds described in Examples 1 to 7.
ピリドンモノアゾ化合物 ５部尿
素 ５部ア
ルギン酸ソーダ（５％）元糊 ５０部熱
湯 ２５部重
曹 ２
部バランス １３部
この色糊をシルケット加工線ブロード上に印捺し、中間
乾燥後、１００℃で５分間スチーミングを行い、湯洗い
、ソーピング、湯洗いそして乾燥し、諸堅牢度に優れた
黄色の捺染物が得られた。Pyridone monoazo compound 5 parts urine
Base: 5 parts Sodium alginate (5%) Base paste: 50 parts Heat
Hot water 25 parts weight
Cao 2
Part Balance Part 13 This color paste is printed on broad mercerized wire, and after intermediate drying, it is steamed at 100℃ for 5 minutes, washed with hot water, soaped, washed with hot water, and dried to produce a yellow color with excellent color fastness. A printed product was obtained.
（以下余白）(Margin below)
Claims (3)
換のピリジニオ基を、Ｚ＿１およびＺ＿２は互いに独立
に−ＳＯ＿２ＣＨ＝ＣＨ＿２又は −ＳＯ＿２ＣＨ＿２ＣＨ＿２Ｚ′を表し、Ｚはアルカリ
の作用で脱離する基を表す。Ａは置換されていてもよい
フェニレン、ナフチレンまたはアルキレン基を表す。Ｒ
＿１は水素又は置換されていてもよいアルキル基を、Ｒ
＿２、Ｒ＿３、Ｒ＿４およびＲ＿５は互いに独立に水素
または置換されていてもよいアルキル、フェニル、ナフ
チルもしくはベンジル基を表す。Ｒ＿６は水素又は置換
されていてもよいアルキル基を、Ｒ＿７は水素、シアノ
基、カルバモイル基、スルホ基、スルホアルキル基また
はハロゲン基を、Ｒ＿８はアルキル基を表す。Ｄは置換
されていてもよいフェニレンまたはナフチレン基を表す
。Ｗはアルキレン基をあらわす。〕 で示されるピリドンモノアゾ化合物。(1) In the form of free acid, there are the following general formulas ▲ mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, X is ▲ mathematical formulas, chemical formulas, tables, etc. ▼, -OR_4 or -SR_5, Y is substituted or an unsubstituted pyridinio group, Z_1 and Z_2 independently represent -SO_2CH=CH_2 or -SO_2CH_2CH_2Z', and Z represents a group that is eliminated by the action of an alkali. A represents an optionally substituted phenylene, naphthylene or alkylene group. R
_1 is hydrogen or an optionally substituted alkyl group, R
_2, R_3, R_4 and R_5 each independently represent hydrogen or an optionally substituted alkyl, phenyl, naphthyl or benzyl group. R_6 represents hydrogen or an optionally substituted alkyl group, R_7 represents hydrogen, a cyano group, a carbamoyl group, a sulfo group, a sulfoalkyl group, or a halogen group, and R_8 represents an alkyl group. D represents an optionally substituted phenylene or naphthylene group. W represents an alkylene group. ] A pyridone monoazo compound represented by
換されていてもよいフェニレン又はナフチレン基である
、請求項１に記載の化合物。(2) The compound according to claim 1, wherein D has a sulfo group at the ortho position of the azo group and is an optionally substituted phenylene or naphthylene group.
ることを特徴とする繊維材料の染色または捺染方法。(3) A method for dyeing or printing textile materials, which comprises using the pyridone monoazo compound according to claim 1.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1-141855 | 1989-06-01 | ||
| JP14185589 | 1989-06-01 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0388862A true JPH0388862A (en) | 1991-04-15 |
| JP2861196B2 JP2861196B2 (en) | 1999-02-24 |
Family
ID=15301734
Family Applications (13)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP427990A Pending JPH0388857A (en) | 1989-06-01 | 1990-01-10 | Monoazopyrazolone compound and method for dyeing or printing textile material using the same |
| JP2004276A Pending JPH0388865A (en) | 1989-06-01 | 1990-01-10 | Monoazoacetoacetic acid compound and method for dyeing or printing textile material using the same |
| JP2005150A Expired - Lifetime JP2861174B2 (en) | 1989-06-01 | 1990-01-11 | Monoazo compound and method for dyeing or printing fiber material using the same |
| JP514990A Pending JPH0388866A (en) | 1989-06-01 | 1990-01-11 | Acetoacetic acid monoazo compound and method for dyeing or printing textile material using the same |
| JP02007500A Expired - Lifetime JP3030460B2 (en) | 1989-06-01 | 1990-01-16 | Monoazo compound and method for dyeing or printing fiber material using the same |
| JP3493890A Pending JPH0388863A (en) | 1989-06-01 | 1990-02-14 | Pyrazolone monoazo compound and method for dyeing or printing textile material using the same |
| JP2034937A Expired - Lifetime JP2861196B2 (en) | 1989-06-01 | 1990-02-14 | Pyridone monoazo compound and method for dyeing or printing fiber material using the same |
| JP3574690A Pending JPH0388853A (en) | 1989-06-01 | 1990-02-15 | Formazan compound and method for dyeing or printing fiber material using same compound |
| JP2036892A Expired - Lifetime JP2853239B2 (en) | 1989-06-01 | 1990-02-16 | Bisazo compound and method for dyeing or printing fiber material using the same |
| JP3688990A Pending JPH0388855A (en) | 1989-06-01 | 1990-02-16 | Dioxazine compound and method for dyeing or printing fiber material using same compound |
| JP2036893A Pending JPH0388872A (en) | 1989-06-01 | 1990-02-16 | Trisazo compound and method for dyeing or printing fiber material with the same |
| JP3688890A Pending JPH0388874A (en) | 1989-06-01 | 1990-02-16 | Phthalocyanine compound and method for dyeing or printing fiber material with the same |
| JP2118079A Pending JPH03250057A (en) | 1989-06-01 | 1990-05-07 | Bisazo compound, and method for dyeing or printing fibrous material therewith |
Family Applications Before (6)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP427990A Pending JPH0388857A (en) | 1989-06-01 | 1990-01-10 | Monoazopyrazolone compound and method for dyeing or printing textile material using the same |
| JP2004276A Pending JPH0388865A (en) | 1989-06-01 | 1990-01-10 | Monoazoacetoacetic acid compound and method for dyeing or printing textile material using the same |
| JP2005150A Expired - Lifetime JP2861174B2 (en) | 1989-06-01 | 1990-01-11 | Monoazo compound and method for dyeing or printing fiber material using the same |
| JP514990A Pending JPH0388866A (en) | 1989-06-01 | 1990-01-11 | Acetoacetic acid monoazo compound and method for dyeing or printing textile material using the same |
| JP02007500A Expired - Lifetime JP3030460B2 (en) | 1989-06-01 | 1990-01-16 | Monoazo compound and method for dyeing or printing fiber material using the same |
| JP3493890A Pending JPH0388863A (en) | 1989-06-01 | 1990-02-14 | Pyrazolone monoazo compound and method for dyeing or printing textile material using the same |
Family Applications After (6)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3574690A Pending JPH0388853A (en) | 1989-06-01 | 1990-02-15 | Formazan compound and method for dyeing or printing fiber material using same compound |
| JP2036892A Expired - Lifetime JP2853239B2 (en) | 1989-06-01 | 1990-02-16 | Bisazo compound and method for dyeing or printing fiber material using the same |
| JP3688990A Pending JPH0388855A (en) | 1989-06-01 | 1990-02-16 | Dioxazine compound and method for dyeing or printing fiber material using same compound |
| JP2036893A Pending JPH0388872A (en) | 1989-06-01 | 1990-02-16 | Trisazo compound and method for dyeing or printing fiber material with the same |
| JP3688890A Pending JPH0388874A (en) | 1989-06-01 | 1990-02-16 | Phthalocyanine compound and method for dyeing or printing fiber material with the same |
| JP2118079A Pending JPH03250057A (en) | 1989-06-01 | 1990-05-07 | Bisazo compound, and method for dyeing or printing fibrous material therewith |
Country Status (1)
| Country | Link |
|---|---|
| JP (13) | JPH0388857A (en) |
-
1990
- 1990-01-10 JP JP427990A patent/JPH0388857A/en active Pending
- 1990-01-10 JP JP2004276A patent/JPH0388865A/en active Pending
- 1990-01-11 JP JP2005150A patent/JP2861174B2/en not_active Expired - Lifetime
- 1990-01-11 JP JP514990A patent/JPH0388866A/en active Pending
- 1990-01-16 JP JP02007500A patent/JP3030460B2/en not_active Expired - Lifetime
- 1990-02-14 JP JP3493890A patent/JPH0388863A/en active Pending
- 1990-02-14 JP JP2034937A patent/JP2861196B2/en not_active Expired - Lifetime
- 1990-02-15 JP JP3574690A patent/JPH0388853A/en active Pending
- 1990-02-16 JP JP2036892A patent/JP2853239B2/en not_active Expired - Lifetime
- 1990-02-16 JP JP3688990A patent/JPH0388855A/en active Pending
- 1990-02-16 JP JP2036893A patent/JPH0388872A/en active Pending
- 1990-02-16 JP JP3688890A patent/JPH0388874A/en active Pending
- 1990-05-07 JP JP2118079A patent/JPH03250057A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0388865A (en) | 1991-04-15 |
| JPH03250057A (en) | 1991-11-07 |
| JPH0388853A (en) | 1991-04-15 |
| JPH0388874A (en) | 1991-04-15 |
| JPH0388871A (en) | 1991-04-15 |
| JPH0388866A (en) | 1991-04-15 |
| JPH0388857A (en) | 1991-04-15 |
| JP2861174B2 (en) | 1999-02-24 |
| JPH0388859A (en) | 1991-04-15 |
| JPH0388855A (en) | 1991-04-15 |
| JPH0388869A (en) | 1991-04-15 |
| JP2853239B2 (en) | 1999-02-03 |
| JP2861196B2 (en) | 1999-02-24 |
| JPH0388872A (en) | 1991-04-15 |
| JPH0388863A (en) | 1991-04-15 |
| JP3030460B2 (en) | 2000-04-10 |
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