JPH0425311B2 - - Google Patents
Info
- Publication number
- JPH0425311B2 JPH0425311B2 JP58050205A JP5020583A JPH0425311B2 JP H0425311 B2 JPH0425311 B2 JP H0425311B2 JP 58050205 A JP58050205 A JP 58050205A JP 5020583 A JP5020583 A JP 5020583A JP H0425311 B2 JPH0425311 B2 JP H0425311B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- compound
- formula
- dyeing
- general formula
- 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 - Lifetime
Links
- -1 bisazo compound Chemical class 0.000 claims description 68
- 238000004043 dyeing Methods 0.000 claims description 36
- 150000003839 salts Chemical class 0.000 claims description 15
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 239000003513 alkali Substances 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000004957 naphthylene group Chemical group 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 230000009471 action Effects 0.000 claims description 3
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 3
- PDKSBUDYYWLQGH-UHFFFAOYSA-N propan-2-yl 2-[benzyl-[2-[benzyl-(2-oxo-2-propan-2-yloxyethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=CC=1CN(CC(=O)OC(C)C)CCN(CC(=O)OC(C)C)CC1=CC=CC=C1 PDKSBUDYYWLQGH-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 41
- 235000002639 sodium chloride Nutrition 0.000 description 20
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 16
- 239000002253 acid Substances 0.000 description 13
- 239000000047 product Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- 239000000975 dye Substances 0.000 description 10
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
- 229920003043 Cellulose fiber Polymers 0.000 description 7
- 239000000835 fiber Substances 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 230000007935 neutral effect Effects 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 238000009833 condensation Methods 0.000 description 5
- 230000005494 condensation Effects 0.000 description 5
- 239000002657 fibrous material Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- 238000006193 diazotization reaction Methods 0.000 description 4
- 239000003792 electrolyte Substances 0.000 description 4
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 4
- 238000005185 salting out Methods 0.000 description 4
- 235000010288 sodium nitrite Nutrition 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000010446 mirabilite Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- 238000010025 steaming Methods 0.000 description 3
- 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
- LTPSRQRIPCVMKQ-UHFFFAOYSA-N 2-amino-5-methylbenzenesulfonic acid Chemical compound CC1=CC=C(N)C(S(O)(=O)=O)=C1 LTPSRQRIPCVMKQ-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 229920000297 Rayon Polymers 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 125000005521 carbonamide group Chemical group 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000012263 liquid product Substances 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 159000000001 potassium salts Chemical class 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000017550 sodium carbonate Nutrition 0.000 description 2
- 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 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 210000004243 sweat Anatomy 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
- MBDUIEKYVPVZJH-UHFFFAOYSA-N 1-ethylsulfonylethane Chemical compound CCS(=O)(=O)CC MBDUIEKYVPVZJH-UHFFFAOYSA-N 0.000 description 1
- 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 1
- GWIAAIUASRVOIA-UHFFFAOYSA-N 2-aminonaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(N)=CC=C21 GWIAAIUASRVOIA-UHFFFAOYSA-N 0.000 description 1
- 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
- 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
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 description 1
- APRRQJCCBSJQOQ-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-2,7-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(N)=CC(S(O)(=O)=O)=CC2=C1 APRRQJCCBSJQOQ-UHFFFAOYSA-N 0.000 description 1
- HMNPDEGBVWDHAR-UHFFFAOYSA-N 8-aminonaphthalen-1-ol Chemical compound C1=CC(O)=C2C(N)=CC=CC2=C1 HMNPDEGBVWDHAR-UHFFFAOYSA-N 0.000 description 1
- 240000008564 Boehmeria nivea Species 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 1
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 1
- 240000000491 Corchorus aestuans Species 0.000 description 1
- 235000011777 Corchorus aestuans Nutrition 0.000 description 1
- 235000010862 Corchorus capsularis Nutrition 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 229920000571 Nylon 11 Polymers 0.000 description 1
- 229920001007 Nylon 4 Polymers 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 239000004115 Sodium Silicate Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 239000004280 Sodium formate Substances 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- SAQSTQBVENFSKT-UHFFFAOYSA-M TCA-sodium Chemical compound [Na+].[O-]C(=O)C(Cl)(Cl)Cl SAQSTQBVENFSKT-UHFFFAOYSA-M 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000005997 bromomethyl group Chemical group 0.000 description 1
- 235000009120 camo Nutrition 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
- 235000005607 chanvre indien Nutrition 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000010016 exhaust dyeing Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 210000004209 hair Anatomy 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000010409 ironing Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920006306 polyurethane fiber Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 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
- 239000000985 reactive dye Substances 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 229940005550 sodium alginate Drugs 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
- BEYHQWDNTWZATJ-UHFFFAOYSA-M sodium;3,6-disulfonaphthalen-1-olate Chemical compound [Na+].[O-]C1=CC(S(O)(=O)=O)=CC2=CC(S(=O)(=O)O)=CC=C21 BEYHQWDNTWZATJ-UHFFFAOYSA-M 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Landscapes
- Coloring (AREA)
Description
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The present invention relates to a bisazo compound and a method of dyeing or printing using the same. For more details,
The present invention relates to a compound that has fiber reactivity and is capable of dyeing or printing fibers in navy color, and to dyeing or printing fibers using the compound. Conventionally, known reactive dyes that give navy colors used for this purpose have been insufficient in terms of dyeing performance and fastness. As a result of intensive studies aimed at improving these points, the present inventors have discovered that a compound having a specific structure or a salt thereof has excellent performance, and has completed the present invention. The present invention is based on the following general formula () [Wherein, X is a halogen atom, R1 is an optionally substituted lower alkyl group, R2 is a hydrogen atom or an optionally substituted lower alkyl group, R3 is a hydrogen atom or a methyl group, Z1 , Z 2 and Z 3 are each independently a hydrogen atom, a chlorine atom, a methyl group, a methoxy group,
Ethyl group, ethoxy group, sulfonic acid group or carboxylic acid group, Z 4 and Z 5 are amino groups on one side and hydroxyl groups on the other side, A is phenylene group or naphthylene group which may have a substituent, Y is -SO 2 CH=CH 2 or -
SO 2 CH 2 CH 2 Z, Z represents a group that is eliminated by the action of an alkali. ] The present invention relates to a bisazo compound or a salt thereof, and a method of dyeing or printing using the same. Among the above general formulas (), especially the following general formula (-1) [In the formula, R 1 , Z 2 , Z 3 , Z 4 , Z 5 , A and Y have the above-mentioned meanings. ] A bisazone compound or a salt thereof represented by these is preferred. In the general formula (), X is a chlorine atom, a fluorine atom or a bromine atom, and the former two are preferred;
Particularly preferred is a chlorine atom. The compounds of the invention may exist in the form of free acids, but are preferably alkali metal or alkaline earth metal salts, especially sodium and potassium salts. The compound of the present invention can be produced by a known method or in accordance therewith. For example, the following general formula () [In the formula, R 1 and R 3 have the above meanings. ] Aromatic sulfonic acid or its salt and the following general formula () [In the formula, R 1 , A and Y have the above meanings.] ] in an aqueous medium in any order,
Primarily, PH1 to PH at a temperature of -10â to 40â
While adjusting the temperature to
While adjusting the pH to 2 to 9 at °C, use the following general formula () [In the formula, X has the above meaning. ] Condensation with the trihalogenotriazine represented by the following general formula () [In the formula, R 1 , R 2 , R 3 , A, X and Y have the above-mentioned meanings. ] or a salt thereof is obtained. A compound obtained by diazotizing this using a conventional method,
General formula below () [In the formula, Z 1 , Z 2 and Z 3 have the above meanings. ] A compound obtained by diazotizing the compound shown by a conventional method in an aqueous medium in any order, firstly at a temperature of -10 to 40°C and a pH of 0 to 4, and secondarily at a temperature of - It can be produced by reacting with 1-amino-8-hydroxynaphthalene-3,6-disulfonic acid or a salt thereof at 10-40°C and pH 3-9. Alternatively, the compounds represented by the above general formulas () and () are condensed at a temperature of -10 to 40°C and a pH of 1 to 9, and then diazotized, and this is combined with the above general formulas () and 1-amino-8-hydroxynaphthalene. -3,6-disulfonic acid or its salt is reacted stepwise by the method described above, and then the compound represented by the general formula () is reacted at a temperature of 0°C to 70°C, PH
It can also be produced by condensing 2 to 9. In the general formula (), the lower alkyl group represented by R 1 and R 2 is preferably an alkyl group having 1 to 4 carbon atoms, and the optionally substituted groups include a hydroxy group, a cyano group,
Preferred are an alkoxy group, a halogen group, a carboxy group, a carbamoyl group, an alkoxycarbonyl group, an alkylcarbonyloxy group, a sulfo group, and a sulfamoyl group. Particularly preferable examples of R 1 include methyl group, ethyl group, n-propyl group, iso-propyl group, n-butyl group, iso-butyl group, sec-butyl group, 2-hydroxyethyl group, 2-hydroxyethyl group, and 2-hydroxyethyl group. Roxypropyl group, 3-hydroxypropyl group, 2-hydroxybutyl group, 3-hydroxybutyl group, 4
- hydroxybutyl group, 2,3-dihydroxypropyl group, 3,4-dihydroxybutyl group, cyanomethyl group, 2-cyanoethyl group, 3-cyanopropyl group, methoxymethyl group, ethoxymethyl group,
2-methoxyethyl group, 2-ethoxyethyl group,
3-methoxypropyl group, 3-ethoxypropyl group, 2-hydroxy-3-methoxypropyl group,
Chloromethyl group, bromomethyl group, 2-chloroethyl group, 2-bromoethyl group, 3-chloropropyl group, 3-bromopropyl group, 4-chlorobutyl group, 4-bromobutyl group, carboxymethyl group,
2-carboxyethyl group, 3-carboxypropyl group, 4-carboxybutyl group, 1,2-dicarboxyethyl group, carbamoylmethyl group, 2-carbamoylethyl group, 3-carbamoylpropyl group, 4-carbamoylbutyl group, methoxy Carbonylmethyl group, ethoxycarbonylmethyl group, 2
-methoxycarbonylethyl group, 2-ethoxycarbonylethyl group, 3-methoxycarbonylpropyl group, 3-ethoxycarbonylpropyl group, 4
-Methoxycarbonylbutyl group, 4-ethoxycarbonylbutyl group, methylcarbonyloxymethyl group, ethylcarbonyloxymethyl group, 2-methylcarbonyloxyethyl group, 2-ethylcarbonyloxyethyl group, 3-methylcarbonyloxypropyl group, 3 -Ethylcarbonyloxypropyl group, 4-methylcarbonyloxybutyl group, 4-ethylcarbonyloxybutyl group, sulfomethyl group, 2-sulfoethyl group, 3-sulfopropyl group, 4-sulfobutyl group, sulfamoylmethyl group, 2- Examples include sulfamoylethyl group, 3-sulfamoylpropyl group, 4-sulfamoylbutyl group, and the like. Particularly preferable examples of R 2 include hydrogen and the above-mentioned substituted or unsubstituted alkyl groups exemplified for R 1 . A is a phenylene group or a sulfonic acid group optionally substituted with one or two substituents, preferably selected from the group of methyl group, ethyl group, methoxy group, ethoxy group, chlorine, bromine, and sulfonic acid group. A naphthylene group which may be substituted with one group, for example,
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ãã[Formula] means a bond leading to a group). etc. can be given. and Y is the group SO 2 CH=CH 2 or the group âSO 2 CH 2
It represents CH 2 Z, where Z is a group that is eliminated with an alkali, such as a sulfate ester group, a thiosulfate ester group, a phosphate ester group, an acetate ester group, a halogen atom, and the like. Depending on the reaction conditions, the starting compounds mentioned are used in the form of acids and/or salts, in particular alkali metal or alkaline earth metal salts. In order to obtain a desired counter ion in the bisazo compound of the present invention, the type of counter ion in the starting compound, the type of alkaline agent used to neutralize the acid during the production process, or the electrolyte used in salting out and isolation as necessary. This is possible by selecting the type of The bisazo compound produced according to the present invention can be made into a liquid product by removing inorganic salts and adding a stabilizer or a dyeability improver as necessary, or this liquid product or reaction solution It can be made into a powder product by evaporation, for example by spray drying, and it can also be made into a liquid or powder product through salting out separation by addition of an electrolyte using a generally known method. 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. Hydroxy-containing materials are natural or synthetic hydroxy group-containing materials, such as cellulose fiber materials or their regenerated products and polyvinyl alcohol.
The cellulosic fiber material is preferably cotton, but also other vegetable fibers such as linen, hemp, jute and ramie fibers. Regenerated cellulose fibers are, for example, viscose staple and filament viscose. 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-, polyamide-11 and polyamide-4. . 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. For example, when exhaust dyeing is carried out on cellulose fibers, in the presence of an acid binder such as soda carbonate, sodium phosphate, caustic soda, etc., a neutral salt, such as mirabilite or common salt, is optionally added and, if desired, dissolved. It is carried out at relatively low temperatures using auxiliaries, penetrants or leveling agents. 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. When dyeing cellulose fibers according to the padzink method, it can be padded at room temperature or at an elevated temperature and, after drying, fixed by steaming or dry heat. When printing is carried out on cellulose fibers, it can be carried out in one phase, for example by printing with a printing paste containing baking soda or other acid binders and then steaming at 100-160°C, or in two phases. For example, it can be carried out by printing with a neutral or weakly acidic printing paste, passing it through a hot alkaline bath containing an electrolyte, or overpadding with a padding liquid containing an alkaline electrolyte, followed by steaming or dry heat treatment. 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. Suitable acid binders for fixing 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 under heated conditions. 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. Dyeing of synthetic and natural polyamide and polyurethane fibers begins with an acidic or weakly acidic dye bath.
This can be done by controlling the exhaustion and then changing the PH value to a neutral, or even alkaline, value for fixation. 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 condensate of cyanuric chloride and 3 times the molar amount of aminobenzenesulfonic acid or aminonaphthalenesulfonic acid or For example, addition products of stearylamine and ethylene oxide can also be used. The compound of the present invention is characterized in that it exhibits excellent performance in dyeing and printing textile materials.
Particularly suitable for dyeing cellulose fiber materials,
Good light and sweat resistance, good moisture resistance, such as washing resistance, peroxide washing resistance, sweat resistance, acid hydrolysis resistance and alkali resistance, as well as good abrasion resistance and ironing resistance. has. In addition, it has excellent build-up properties, level dyeing properties, and wash-off properties, as well as good solubility and high exhaustion and fixation properties.
It is characterized by being less susceptible to fluctuations in dyeing temperature and dye bath ratio and producing dyed products of stable quality. Among them, compounds in which Z 4 is an amino group and Z 5 is a hydroxyl group in the general formula () have excellent chlorine water resistance and chlorine bleach resistance, and in particular, compounds in the general formula (
The compound represented by -1) also has extremely excellent formalin resistance and formalin-light fastness. Hereinafter, the present invention will be explained in detail with reference to Examples.
In the examples, parts and % indicate parts by weight and % by weight, respectively. Example 1 Add 4.71 parts of 4-methylaniline-2-sulfonic acid and 3.7 parts of concentrated hydrochloric acid to 25 parts of ice water, and heat at 0 to 5°C for 35 minutes.
Diazotization is carried out by injecting 5.1 parts of % sodium nitrite solution. After eliminating excess nitrite, 1-amino-
A neutral solution of 7.81 parts of 8-hydroxynaphthalene-3,6-disulfonic acid monosodium salt was added at 0 to 10°C.
It takes about 1 hour to inject and couple at pH 0.5 to 1.5. After stirring this mixture for several hours, it is neutralized with a caustic soda solution to a pH of 7, and salted out with sodium chloride at 30 to 35°C to obtain a monoazo dye. On the other hand, 4.61 parts of cyanuric chloride and 4.70 parts of m-phenylenediaminesulfonic acid were heated to pH 6-7 in 50 parts of water by keeping at 0-5°C for 1-2 hours to carry out the first condensation, and then 1-N -ethylaminobenzene-3
A second condensation is carried out by adding 7.64 parts of -β-sulfatoethyl sulfone and stirring overnight at 25-30° C. while maintaining the pH at 5-5.5 with 9% sodium bicarbonate solution. Then, after adding 50 parts of ice and 7.1 parts of concentrated hydrochloric acid,
Diazotization is carried out by adding 5.3 parts of % sodium nitrite solution. The diazotized solution from which the residual nitrous acid has been removed is poured into a monoazo dye suspension made alkaline with sodium bicarbonate at 5 to 10°C, and the mixture is stirred for 1 to 2 hours to perform coupling. After adjusting the pH to 5.5 to 6.0 with dilute sulfuric acid and the temperature to 50 to 55°C, add sodium chloride to the solution for salting out, filter, wash, and dry at 60°C. The produced bisazone compound, in the form of free acid, has the following formula: (Maximum input = 600 nm, however, in an aqueous solvent, measured under the same conditions below). Dissolve 0.1, 0.3 and 0.6 parts of the obtained bisazo compounds in 200 parts of water, add 10 parts of Glauber's salt and 10 parts of cotton, raise the temperature to 60°C, add 4 parts of soda carbonate, and dye for 1 hour. After washing with water, soaping, washing with water and drying, a greenish navy with excellent fastness, especially chlorine fastness, formalin fastness, and formalin-light fastness, extremely good build-up properties and good technical dyeing properties. A colored dyeing was obtained. This compound also had excellent solubility and showed good level dyeing and dyeing reproducibility. Examples 2 to 18 The corresponding bisazo compounds were synthesized using the following raw materials in the same manner as in Example 1. The bisazo compounds shown below contain 1-amino-8-hydroxynaphthalene- as the azo component.
Using 3,6-disulfonic acid disodium salt, the diazo component of the monoazo compound [the compound of the above general formula ()]: Column A, the aromatic sulfone constituting the diazo component of the disazo compound [the compound of the above general formula ()] Acid [compound of the above general formula ()]: Column B,
Compound of the above general formula (): Column C, and trihalogenotriazine [compound of the above general formula ()]:
It is characterized by Column D and the color tone of the dyed product obtained by dyeing by the same method as in Example 1: Column E.
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ãããã[Table] Example 19 Each was dyed in the same manner as in Example 1 except that the bisazo compound of Example 2-18 was used, and various fastnesses were determined, especially chlorine fastness, formalin fastness, and formalin-light fastness. A dyed product was obtained which had excellent strength and extremely good technical dyeability. These compounds had excellent solubility and showed good level dyeing and dyeing reproducibility. Examples 20 to 35 The corresponding bisazo compounds were synthesized using the following raw materials in the same manner as in Example 1. The bisazo compounds shown below contain 1-amino-8-hydroxynaphthalene- as the azo component.
Using disodium 3,6-disulfonate, the diazo component of the monoazo compound [the compound of the above general formula ()]: Column A, the aromatic sulfonic acid constituting the diazo component of the disazo compound [the compound of the above general formula ()] [Compound of the above general formula ()]: Column B, and compound of the above general formula (): Column C, and trihalogenotriazine [Compound of the above general formula ()]: Column D, and the same method as Example 1. The color tone of the dyed product obtained by dyeing with: Characterized by column E.
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æè²ç©ã®è²èª¿ïŒïŒ¥æ¬ã«ããç¹åŸŽã¥ããããã[Table] Example 36 Each was dyed in the same manner as in Example 1 except that the bisazo compounds of Examples 20 to 35 were used, and the dyes were excellent in various fastnesses, especially chlorine fastness, and had extremely good technical dyeing properties. A dyed product was obtained. These compounds had excellent solubility and showed good level dyeing and dyeing reproducibility. Example 37 First condensation is carried out by keeping 4.61 parts of cyanuric chloride and 4.70 parts of m-phenylenediaminesulfonic acid at pH 6-7 in 50 parts of water at 0-5°C for 1-2 hours,
Next, 7.64 parts of 1-N-ethylaminobenzene-3-β-sulfate ethyl sulfone was added, and the pH was kept at 5-5.5 with 9% sodium bicarbonate solution.
A second condensation is carried out by stirring overnight at 30°C. Next, add 50 parts of ice and 7.1 parts of concentrated hydrochloric acid to 35%
Diazotization is carried out by adding 5.3 parts of sodium nitrite solution. Add 1
-amino-8-hydroxynaphthalene-3,6-
A neutral solution of 7.81 parts of disulfonic acid monosodium salt was injected at 0 to 10°C over about 1 hour to obtain a pH of 0.5 to 2.0.
Perform coupling with. After stirring this mixture for several hours, it was neutralized with a sodium carbonate solution to a pH of 7 and 30
At ~35°C, salt out with sodium chloride to obtain a monoazo dye. Meanwhile, add 4.71 parts of 4-methylaniline-2-sulfonic acid and 3.7 parts of concentrated hydrochloric acid to 25 parts of ice water, and add
Diazotization is carried out by injecting 5.1 parts of 35% sodium nitrite solution. After the residual nitrous acid has disappeared, this is poured into a monoazo dye suspension made alkaline with sodium bicarbonate at 5 to 10°C, and the mixture is stirred for 1 to 2 hours to perform coupling. PH 5.5-6.0 with dilute sulfuric acid
After adjusting the temperature to 50 to 55°C, add sodium chloride to the solution for salting out, filter, wash, and dry at 60°C. The produced bisazone compound, in the form of free acid, has the following formula: (maximum input = 620nm) Dissolve 0.1, 0.3 and 0.6 parts of the obtained bisazo compounds in 200 parts of water, add 10 parts of Glauber's salt and 10 parts of cotton, raise the temperature to 60°C, add 4 parts of soda carbonate, and dye for 1 hour. After washing with water, soaping, washing with water and drying, a greenish navy with excellent fastness, especially chlorine fastness, formalin fastness, and formalin-light fastness, extremely good build-up properties and good technical dyeing properties. A colored dyeing was obtained. This compound also had excellent solubility and showed good level dyeing and dyeing reproducibility. Examples 38 to 54 The corresponding bisazo compounds were synthesized in the same manner as in Example 37 using the following raw materials. The bisazo compounds shown in the table below contain 1-amino-8-hydroxynaphthalene- as the azo component.
Using disodium 3,6-disulfonate, aromatic sulfonic acid [compound of the above general formula ()] constituting the diazo component of the monoazo compound [compound of the above general formula ()]: Column A, of the above general formula () Compound: Column B, and trihalogenotriazine [compound of the above general formula ()]: Column C, diazo component of the disazo compound [compound of the above general formula ()]: Column D,
The color tone of the dyed product obtained by dyeing in the same manner as in Example 37: Characterized by column E.
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è²ã®åçŸæ§ãæããã[Table] Example 55 Dyeing was carried out in the same manner as in Example 37 except that the bisazo compounds of Examples 38 to 54 were used, and various fastnesses were determined, especially chlorine fastness, formalin fastness, and formalin-light fastness. A dyed product with excellent dyeing properties was obtained. This compound also had excellent solubility and good level dyeing and dyeing reproducibility.
Claims (1)
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æè²åã¯æºæããæ¹æ³ã[Claims] 1. The following general formula () [Wherein, X is a halogen atom, R 1 is an optionally substituted lower alkyl group, R 2 is a hydrogen atom or an optionally substituted lower alkyl group, R 3 is a hydrogen atom or a methyl group, R 1 , Z 2 and Z 3 are each independently a hydrogen atom, a chlorine atom, a methyl group, a methoxy group, an ethyl group, an ethoxy group, a sulfonic acid group or a carboxylic acid group, and Z 4 and Z 5 are one of amino groups and the other of hydroxyl groups, A is a phenylene group or a naphthylene group which may have a substituent, Y is -SO2CH = CH2 or -SO2CH2CH2Z , and Z represents a group that is eliminated by the action of an alkali. ] A bisazo compound or a salt thereof. 2 General formula (-1) below [In the formula, R 1 , Z 2 , Z 3 , Z 4 , Z 5 , A and Y have the same meaning as described in claim 1. ] A bisazo compound or a salt thereof according to claim 1. 3 General formula below () [Wherein, X is a halogen atom, R1 is an optionally substituted lower alkyl group, R2 is a hydrogen atom or an optionally substituted lower alkyl group, R3 is a hydrogen atom or a methyl group, Z1 , Z 2 and Z 3 are each independently a hydrogen atom, a chlorine atom, a methyl group, a methoxy group,
Ethyl group, ethoxy group, sulfonic acid group or carboxylic acid group, Z 4 and Z 5 are amino groups on one side and hydroxyl groups on the other side, A is phenylene group or naphthylene group which may have a substituent, Y is -SO 2 CH=CH 2 or -
SO 2 CH 2 CH 2 Z, Z represents a group that is eliminated by the action of an alkali. ] Using the bisazo compound or its salt shown in
A method of dyeing or printing.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP58050205A JPS59174652A (en) | 1983-03-24 | 1983-03-24 | Bisazo compound and dyeing or textile printing using the same |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP58050205A JPS59174652A (en) | 1983-03-24 | 1983-03-24 | Bisazo compound and dyeing or textile printing using the same |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS59174652A JPS59174652A (en) | 1984-10-03 |
JPH0425311B2 true JPH0425311B2 (en) | 1992-04-30 |
Family
ID=12852605
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP58050205A Granted JPS59174652A (en) | 1983-03-24 | 1983-03-24 | Bisazo compound and dyeing or textile printing using the same |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS59174652A (en) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3420467A1 (en) * | 1984-06-01 | 1985-12-05 | Basf Ag, 6700 Ludwigshafen | REACTIVE DYES |
GB0006029D0 (en) * | 2000-03-14 | 2000-05-03 | Clariant Int Ltd | Organic compounds |
JPWO2020246342A1 (en) * | 2019-06-06 | 2020-12-10 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS57167462A (en) * | 1981-04-07 | 1982-10-15 | Sumitomo Chemical Co | Dyeing of cellulosic fiber |
-
1983
- 1983-03-24 JP JP58050205A patent/JPS59174652A/en active Granted
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS57167462A (en) * | 1981-04-07 | 1982-10-15 | Sumitomo Chemical Co | Dyeing of cellulosic fiber |
Also Published As
Publication number | Publication date |
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JPS59174652A (en) | 1984-10-03 |
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