JPH02209970A - Asymmetric dioxazine compound and dyeing or pringing of fiber material using the same - Google Patents
Asymmetric dioxazine compound and dyeing or pringing of fiber material using the sameInfo
- Publication number
- JPH02209970A JPH02209970A JP1031496A JP3149689A JPH02209970A JP H02209970 A JPH02209970 A JP H02209970A JP 1031496 A JP1031496 A JP 1031496A JP 3149689 A JP3149689 A JP 3149689A JP H02209970 A JPH02209970 A JP H02209970A
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- dyeing
- resistance
- asymmetric dioxazine
- 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 dioxazine compound Chemical class 0.000 title claims abstract description 84
- 238000004043 dyeing Methods 0.000 title claims abstract description 21
- 239000002657 fibrous material Substances 0.000 title claims abstract description 9
- 239000002253 acid Substances 0.000 claims abstract description 20
- 150000001875 compounds Chemical class 0.000 claims abstract description 15
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims abstract description 8
- 239000003513 alkali Substances 0.000 claims abstract description 7
- 125000004957 naphthylene group Chemical group 0.000 claims abstract description 6
- 230000009471 action Effects 0.000 claims abstract description 4
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Chemical group 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000005156 substituted alkylene group Chemical group 0.000 claims 1
- PPSZHCXTGRHULJ-UHFFFAOYSA-N dioxazine Chemical compound O1ON=CC=C1 PPSZHCXTGRHULJ-UHFFFAOYSA-N 0.000 abstract description 15
- 239000000463 material Substances 0.000 abstract description 11
- 125000000217 alkyl group Chemical group 0.000 abstract description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 8
- 150000001412 amines Chemical class 0.000 abstract description 6
- 229910052736 halogen Inorganic materials 0.000 abstract description 6
- 125000003118 aryl group Chemical group 0.000 abstract description 5
- 125000002947 alkylene group Chemical group 0.000 abstract description 4
- 125000001931 aliphatic group Chemical group 0.000 abstract description 3
- 210000004243 sweat Anatomy 0.000 abstract description 3
- 125000003368 amide group Chemical group 0.000 abstract description 2
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 238000010409 ironing Methods 0.000 abstract 1
- 238000009736 wetting Methods 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 description 14
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 9
- 229920003043 Cellulose fiber Polymers 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000000835 fiber Substances 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 235000002639 sodium chloride Nutrition 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000002367 halogens Chemical group 0.000 description 5
- 125000000623 heterocyclic group Chemical group 0.000 description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
- 239000011230 binding agent Substances 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 238000010025 steaming Methods 0.000 description 4
- 229950000244 sulfanilic acid Drugs 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 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 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 3
- 239000004952 Polyamide Substances 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
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000004132 cross linking 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
- 150000005125 dioxazines Chemical class 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229920002647 polyamide Polymers 0.000 description 3
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- 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 2
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-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
- XBIPSZHQOHLUPK-UHFFFAOYSA-N 7-amino-2h-naphthalene-1,1,3-trisulfonic acid Chemical compound C1=C(S(O)(=O)=O)CC(S(O)(=O)=O)(S(O)(=O)=O)C2=CC(N)=CC=C21 XBIPSZHQOHLUPK-UHFFFAOYSA-N 0.000 description 2
- WXKWWBWCMOQLOP-UHFFFAOYSA-N 8-aminonaphthalene-1,3-disulfonic acid Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=C2C(N)=CC=CC2=C1 WXKWWBWCMOQLOP-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 2
- SUZRRICLUFMAQD-UHFFFAOYSA-N N-Methyltaurine Chemical compound CNCCS(O)(=O)=O SUZRRICLUFMAQD-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-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
- 229920002472 Starch Polymers 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- CREXVNNSNOKDHW-UHFFFAOYSA-N azaniumylideneazanide Chemical group N[N] CREXVNNSNOKDHW-UHFFFAOYSA-N 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
- 125000005521 carbonamide group Chemical group 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 239000003792 electrolyte Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000010985 leather Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 239000010446 mirabilite Substances 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 229920006306 polyurethane fiber 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
- 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
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000003457 sulfones Chemical class 0.000 description 2
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 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
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- RNLJXNUXROETLD-UHFFFAOYSA-N 2-aminobenzene-1,3-disulfonic acid Chemical compound NC1=C(S(O)(=O)=O)C=CC=C1S(O)(=O)=O RNLJXNUXROETLD-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
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-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
- BPGIOCZAQDIBPI-UHFFFAOYSA-N 2-ethoxyethanamine Chemical compound CCOCCN BPGIOCZAQDIBPI-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 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 1
- IMPPGHMHELILKG-UHFFFAOYSA-N 4-ethoxyaniline Chemical compound CCOC1=CC=C(N)C=C1 IMPPGHMHELILKG-UHFFFAOYSA-N 0.000 description 1
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 1
- 240000008564 Boehmeria nivea Species 0.000 description 1
- RJSYPKWVIJGNLO-UHFFFAOYSA-N CCOClOC Chemical compound CCOClOC RJSYPKWVIJGNLO-UHFFFAOYSA-N 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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 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
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 229920000571 Nylon 11 Polymers 0.000 description 1
- 229920001007 Nylon 4 Polymers 0.000 description 1
- 229920002292 Nylon 6 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
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 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
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000004280 Sodium formate Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 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
- 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
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000001691 aryl alkyl amino group Chemical group 0.000 description 1
- 125000001769 aryl amino group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 229940000635 beta-alanine Drugs 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000005997 bromomethyl group Chemical group 0.000 description 1
- 235000009120 camo Nutrition 0.000 description 1
- 125000002837 carbocyclic group Chemical group 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
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 230000008859 change Effects 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
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000002845 discoloration Methods 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
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- 238000010016 exhaust dyeing Methods 0.000 description 1
- 210000004209 hair Anatomy 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003100 immobilizing effect Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 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
- 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
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 239000000985 reactive dye 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
- 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
- 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
- 239000002904 solvent Substances 0.000 description 1
- 229940032147 starch Drugs 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 229960003080 taurine Drugs 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
- C09B62/503—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring the reactive group being an esterified or non-esterified hydroxyalkyl sulfonyl or mercaptoalkyl sulfonyl group, a quaternised or non-quaternised aminoalkyl sulfonyl group, a heterylmercapto alkyl sulfonyl group, a vinyl sulfonyl or a substituted vinyl sulfonyl group, or a thiophene-dioxide group
- C09B62/5033—Dioxazine dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- 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、天然又は合成ポリアミド繊
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、耐光唱牢かつ耐湿
潤堅牢な染色を可能にする改良された新規な非対称ジオ
キサジン化合物、並びにその適用に関する。Detailed Description of the Invention <Industrial Application Field> The present invention is directed to materials containing hydroxyl groups and/or amide groups, particularly cellulose fibers, natural or synthetic polyamide fibers, polyurethane fibers, leather, etc., and blends thereof. The present invention relates to improved novel asymmetric dioxazine compounds suitable for dyeing and printing fibers and allowing light-fast and wet-fast dyeing, and their applications.
〈従来の技術〉
染料の分子構造中にジオキサジン骨格を有する反応染料
は公知であるが、染色性能面、例えば均染性、ビルドア
ツプ性、染色速度において、あるいは堅牢度、特に塩素
堅牢度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> Reactive dyes having a dioxazine skeleton in the molecular structure of the dye are known, but they are insufficient in terms of dyeing performance, such as level dyeing, build-up property, dyeing speed, or fastness, especially chlorine fastness. Therefore, further improvement is desired.
〈発明が解決しようとする問題点〉
ヒドロキシル基及び/又はアミドkを含有する材料の染
色又は捺染物の堅牢度は特にヒドロキシル基含有繊維の
場合において、満足出来るレベルにはなく、本発明者ら
は鋭意このレベルアップに努め、上記問題を解決し得る
非対称ジオキサジン化合物を見い出した。<Problems to be Solved by the Invention> The fastness of dyed or printed products of materials containing hydroxyl groups and/or amide K is not at a satisfactory level, especially in the case of hydroxyl group-containing fibers, and the present inventors worked diligently to improve this level and discovered an asymmetric dioxazine compound that could solve the above problems.
く問題点を解決する為の手段〉
本発明は、遊離酸の形で下記−綴代(I)(以下余白)
〔式中、Xはハロゲンを、Wは置換されていてもよい脂
肪族又は芳香族の架橋基を、Qは置換されてR6
いてもよいアミノ基又は式−青−Y、−Z、で示される
基を、R,、R,、R,、R4,R,およびR6は互い
に独立に水素又は置換基を有していてもよい低級アルキ
ル基を、YlおよびY2は互いに独立に、置換基を有し
ていてもよいアルキレン、フェニレン又はナフチレン基
を、ZlおよびZ2は互いに独立に、−5O2CH−C
H,又は−3o、CH,CH2Z’ (、Z’はアルカ
リの作用で脱離する基を表わす。)を表わす。〕で示さ
れる非対称ジオキサジン化合物及びそれを用いることを
特徴とする繊維材料を染色又は捺染する方法を提供する
ものである。[Means for Solving the Problems] The present invention provides the following in the form of a free acid - Margin (I) (hereinafter referred to as a blank) [In the formula, X is a halogen, and W is an optionally substituted aliphatic or Q is an aromatic crosslinking group, R6 is an optionally substituted amino group or a group represented by the formula -Y, -Z, and R,, R,, R,, R4, R, and R6 are Yl and Y2 independently represent hydrogen or a lower alkyl group that may have a substituent; Yl and Y2 independently represent an alkylene, phenylene, or naphthylene group that may have a substituent; Zl and Z2 independently represent , -5O2CH-C
It represents H, or -3o, CH, CH2Z'(Z' represents a group that is eliminated by the action of an alkali). The present invention provides an asymmetric dioxazine compound represented by the following and a method for dyeing or printing a fiber material using the same.
ここで、Xで示されるハロゲンとしては、塩素または臭
素が好ましい。Here, the halogen represented by X is preferably chlorine or bromine.
Qで示される置換基を有していてもよいアミノ基として
は、アルキルアミノ、N、N−ジアルキルアミノ、ジク
ロアルキルア主ノ、アラールキルアミノ、アリールアミ
ノ、混合置換されたアミノ例えば、N−アルキル−N−
シクロへキシルアミノ及びN−アルキル−N−アリール
アミノ、更に複素環式基を含有するアミノ (この環式
基は更に付加縮合された炭素環式環を有することができ
る。)、及びそのアミノ窒素原子がN−複素環式の環員
であるようなアミノ(このN−複素環は場合によっては
更に別のへテロ原子を含有していてもよい。)などが挙
げられる。上記におけるアルキルは直鎖状でも分校状で
もよく、又低分子のものでも高分子のものでもよいが、
好ましいのは01〜C4のアルキルである。シクロアル
キル、アラールキル及びアリールとしては特にシクロヘ
キシル、ベンジル、フェネチル、フェニルおよびナフチ
ルなどの基が好ましい。複素環式基の例としてはフラン
、チオフェン、ピラゾール、ピリジン、ピリミジン、キ
ノリン、ベンズイミダゾール、ベンズチアゾールおよび
ベンズオキサゾールなどである。アミノ窒素原子がN−
複素環式環の環員であるアミノとして好ましいのは6@
のN−複素環式環化合物であり、これは更にペテロ原子
として窒素、酸素及び硫黄を含有していてもよい。上記
のアルキル、シクロアルキル、アラールキル、アリール
、複素環式環及びN−複素環式環は更に、ハロゲン、ニ
トロ、シアノ、トリフルオロメチル、スルファモイル、
カルバモイル、C1−、、C,−アルキル、C1−C4
って置換されていてもよい。Qで示されるアミノ基の例
としては、−NH,、メチルアミノ、エチルアミノ、プ
ロピルアミノ、ブチルアミノ、ヘキシルアミノ、β−メ
トキシエチルアミノ、β−エトキシエチルアミン、r−
メトキシプロピルアミノ、N、N−ジメチルアミノ、N
、N−ジエチルアミノ、β−クロロエチルアミノ、β−
シアノエチルアミノ、N、N−ジ−β−ヒドロキシエチ
ルアミノ、β−ヒドロキシエチルアミノ、r−ヒドロキ
シプロピルアミノ、ベンジルアミノ、フェネチルアミノ
、シクロへキシルアミノ、N−メチル−N−フェニルア
ミノ、N−エチル−N−フェニルアミノ、N−プロピル
−N−フェニルアミノ、N−ブチル−N−フェニルアミ
ノ、N−β−シアノエチル−N−フェニルアミノ、N−
エチル−2−メチルフェニルアミノ、N−エチル−4−
メチルフェニルアミノ、N−エチル−8−スルホフェニ
ルアミノ、N−エチル−4−スルホフェニルアミノ、フ
ェニルアミノ、トルイジノ、キシリジノ、クロルアニリ
ノ、アニシジン、フェネチジン、2−8−および4−ス
ルホアニリノ、2.4−および2.5−ジスルホアニリ
ノ、スルホメチルアニリノ、N−スルホメチルアニリノ
、B−および4−カルボキシフェニルアミノ、2−カル
ボキシ−5−スルホフェニルアミノ、2−カルボキシ−
4−スルホフェニルアミノ、2−メトキシ−5−スルホ
フェニルアミノ、2−メチル−5−スルホフェニルアミ
ノ、4−スルホナフチル−(1)−アミノ、ホナフチル
ー(2)−アミノ、4.8−ジスルホナフチル−(2)
−アミノ、8.6.8−トリスルホナフチル−(2)−
アミノ、4.6.8−トリスルホナフチル−(2+−ア
ミノ、ビリジルー<21−アミノ、モルホリノ、ピペリ
ジノ、ピペラジノ、エタノールアミノ、メタノールアミ
ノ、N、N−ジェタノールアミノ、N、N−ジメタツー
ルアミノ、N−エタノール−N−メチルアミノおよびN
−エチル−N−メタノールアミクツ−カルボキシエチル
アミノ、β−スルホエチルアミノ、N−(β−スルホエ
チル)−N−メチルアミノ等をあげることができる。Examples of the amino group represented by Q which may have a substituent include alkylamino, N, N-dialkylamino, dichloroalkylamino, aralkylamino, arylamino, mixed substituted amino, for example, N- Alkyl-N-
cyclohexylamino and N-alkyl-N-arylamino, as well as amino containing heterocyclic groups (which cyclic groups can also have addition-fused carbocyclic rings), and their amino nitrogen atoms. Examples include amino in which is an N-heterocyclic ring member (this N-heterocycle may further contain another heteroatom depending on the case). The alkyl in the above may be linear or branched, and may be of low molecular weight or high molecular weight, but
Preferred is alkyl of 01 to C4. As cycloalkyl, aralkyl and aryl, groups such as cyclohexyl, benzyl, phenethyl, phenyl and naphthyl are particularly preferred. Examples of heterocyclic groups include furan, thiophene, pyrazole, pyridine, pyrimidine, quinoline, benzimidazole, benzthiazole and benzoxazole. Amino nitrogen atom is N-
Preferred amino as a ring member of a heterocyclic ring is 6@
is an N-heterocyclic ring compound which may further contain nitrogen, oxygen and sulfur as petro atoms. The above alkyl, cycloalkyl, aralkyl, aryl, heterocyclic ring and N-heterocyclic ring may further be halogen, nitro, cyano, trifluoromethyl, sulfamoyl,
Carbamoyl, C1-, C,-alkyl, C1-C4
may be replaced. Examples of the amino group represented by Q include -NH, methylamino, ethylamino, propylamino, butylamino, hexylamino, β-methoxyethylamino, β-ethoxyethylamine, r-
Methoxypropylamino, N, N-dimethylamino, N
, N-diethylamino, β-chloroethylamino, β-
Cyanoethylamino, N,N-di-β-hydroxyethylamino, β-hydroxyethylamino, r-hydroxypropylamino, benzylamino, phenethylamino, cyclohexylamino, N-methyl-N-phenylamino, N-ethyl- N-phenylamino, N-propyl-N-phenylamino, N-butyl-N-phenylamino, N-β-cyanoethyl-N-phenylamino, N-
Ethyl-2-methylphenylamino, N-ethyl-4-
Methylphenylamino, N-ethyl-8-sulfophenylamino, N-ethyl-4-sulfophenylamino, phenylamino, toluidino, xylidino, chloranilino, anisidine, phenetidine, 2-8- and 4-sulfoanilino, 2.4- and 2,5-disulfoanilino, sulfomethylanilino, N-sulfomethylanilino, B- and 4-carboxyphenylamino, 2-carboxy-5-sulfophenylamino, 2-carboxy-
4-Sulfophenylamino, 2-methoxy-5-sulfophenylamino, 2-methyl-5-sulfophenylamino, 4-sulfonaphthyl-(1)-amino, fonaphthyl-(2)-amino, 4,8-disulfonylamino Naphthyl (2)
-amino,8.6.8-trisulfonaphthyl-(2)-
Amino, 4.6.8-trisulfonaphthyl-(2+-amino, pyridyl<21-amino, morpholino, piperidino, piperazino, ethanolamino, methanolamino, N,N-jetanolamino, N,N-dimethatol amino, N-ethanol-N-methylamino and N
Examples include -ethyl-N-methanolaminocarboxyethylamino, β-sulfoethylamino, and N-(β-sulfoethyl)-N-methylamino.
Yl、Y2 で表わされる置換基を有していても良い
アルキレン基としては、 (CH2) 2 (C
Hz)s−(CH2)10 (CH2)!−などが例示
される。また、置換基を有していてもよいフェニレン基
又はナフチレン基としては、好ましくはメチル、エチル
、メトキシ、エトキシ、塩素、臭素及びスルホの群から
4ばれる、1又は21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1個で置換されていてもよ
いナフチレンであり、たとえば通じている結合を意味す
る。)等をあげることができる。As the alkylene group which may have a substituent represented by Yl, Y2, (CH2) 2 (C
Hz)s-(CH2)10 (CH2)! - etc. are exemplified. Furthermore, the phenylene group or naphthylene group which may have a substituent is preferably substituted with 1 or 21 substituents from the group consisting of methyl, ethyl, methoxy, ethoxy, chlorine, bromine and sulfo. phenylene which may be substituted with phenylene or naphthylene which may be substituted with one sulfo group, and means, for example, a continuous bond. ), etc.
Z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、酢酸ニーステル、ハロゲン等がこれに該当する。Examples of the group represented by Z which is eliminated by the action of an alkali include sulfuric acid ester, thiosulfuric acid ester, phosphoric acid ester, ester acetate, and halogen.
R,、R,%R,、R4,R,及びR−の置換基を有し
ていてもよい低級アルキルとしては、01〜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1.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、スルホ及びスルファモイルが好まし
い。As the lower alkyl which may have a substituent for R,, R, %R,, R4, R, and R-, 01-C4 alkyl is preferable, and as the optionally substituted group, hydroxy , Cyano1. Preferred are a, alkoxy, halogen, carbamoyl, carboxy, alkoxycarbonyl, alkylcarbonyloxy, sulfo and sulfamoyl.
RhRhR,およびR1としては、特に水素が好ましい
。Hydrogen is particularly preferred as RhRhR and R1.
特に好ましいR,及びR・とじては、例えば、水素、メ
チル、エチル、n−プロピル、1so−プロピル、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、8−ヒドロキシ
プロピル、2−ヒドロキシブチル、8−ヒドロキシブチ
ル、4−ヒドロキシブチル、2.8−ジヒドロプロピル
、8.4−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
トキシメチル、2−メトキシエチル、2−エトキシエチ
ル、8−メトキシプロピル、8−エトキシプロピル、2
−ヒドロキシ−8−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、
8−クロロプロピル、8−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、8−カルボキシプロピル、4−カルボ
キシブチル、1.2−ジカルボキシエチル、カルバモイ
ルメチル、2−カルバモイルエチル、8−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、8−
メトキシカルボニルプロピル、8−ヱトキシカルボニル
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−メチルカルボニル
オキシエチル、2−エチルカルボニルオキシエチル、8
−メチルカルボニルオキシプロピル、8−エチルカルボ
ニルオキシプロピル、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、8−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、8−スルフ1モイルプロピル、4−スルフ1モイ
ルブチルをあげることができる。Particularly preferable R and R are, for example, hydrogen, methyl, ethyl, n-propyl, 1so-propyl, n-
Butyl, 1so-butyl, 5ec-butyl, 2-hydroxyethyl, 2-hydroxypropyl, 8-hydroxypropyl, 2-hydroxybutyl, 8-hydroxybutyl, 4-hydroxybutyl, 2.8-dihydropropyl, 8.4 -dihydroxybutyl, cyanomethyl, 2-cyanoethyl, 3-cyanopropyl, methoxymethyl, ethoxymethyl, 2-methoxyethyl, 2-ethoxyethyl, 8-methoxypropyl, 8-ethoxypropyl, 2
-hydroxy-8-methoxypropyl, chloromethyl,
Bromomethyl, 2-chloroethyl, 2-bromoethyl,
8-chloropropyl, 8-bromopropyl, 4-chlorobutyl, 4-bromobutyl, carboxymethyl, 2-carboxyethyl, 8-carboxypropyl, 4-carboxybutyl, 1,2-dicarboxyethyl, carbamoylmethyl, 2-carbamoyl Ethyl, 8-carbamoylpropyl, 4-carbamoylbutyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, 2-methoxycarbonylethyl, 2-ethoxycarbonylethyl, 8-
Methoxycarbonylpropyl, 8-ethoxycarbonylpropyl, 4-methoxycarbonylbutyl, 4-ethoxycarbonylbutyl, methylcarbonyloxymethyl,
Ethylcarbonyloxymethyl, 2-methylcarbonyloxyethyl, 2-ethylcarbonyloxyethyl, 8
-Methylcarbonyloxypropyl, 8-ethylcarbonyloxypropyl, 4-methylcarbonyloxybutyl, 4-ethylcarbonyloxybutyl, sulfomethyl, 2-sulfoethyl, 8-sulfopropyl, 4-sulfobutyl, sulfamoylmethyl, 2-sulfobutyl Famoylethyl, 8-sulf 1 moylpropyl, and 4-sulf 1 moylbutyl can be mentioned.
Wで示される置換されていても良い脂肪族架橋基トシて
はC2〜C4のアルキレン基があげられ、エチレン、プ
ロピレンが特に好ましい。Examples of the optionally substituted aliphatic crosslinking group represented by W include C2 to C4 alkylene groups, with ethylene and propylene being particularly preferred.
R1で表わされるアルキル基の炭素が各々隣接する窒素
と結合して、例えば−NN−のような複素環架橋基を形
成してもよい。Each carbon of the alkyl group represented by R1 may be bonded to an adjacent nitrogen to form a heterocyclic bridging group such as -NN-.
Wで示される置換されていても良い芳香族架橋基として
は、0.1.2または8個のスルホ基により置換されて
いるフェニレン基またはナフチレン基があげられる。The optionally substituted aromatic crosslinking group represented by W includes a phenylene group or a naphthylene group substituted with 0.1.2 or 8 sulfo groups.
本発明化合物は遊離酸の形でまたは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土類金属塩、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 are present in the form of the free acid or in the form of its salts, in particular the alkali metal and alkaline earth 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事ができ
る。下記一般式(If)
So、H
(式中・X・R2・R3・R4,R8およびWは前記の
意味を有する。)
で示される非対称ジオキサジン中間体と下記一般式(@
R7
H−NysZ(ta
(式中、R,、Y、およびZ、は前記の意味を有する。The compound of the present invention can be produced, for example, as follows. An asymmetric dioxazine intermediate represented by the following general formula (If) So, H (in the formula, *X, R2, R3, R4, R8 and W have the above-mentioned meanings) and the following general formula (@ R7 H-NysZ( ta (wherein R,, Y, and Z have the above meanings.
)で示されるアミンおよび下記一般式(5)%式%(5
)
(式中、Qは前記の意味を有する。)
で示されるアミン又は下記一般式(V)R1
糎
H−N−Y、−Z、 (V)(式中、R,
、Y、およびZ、は前記の意味を有する。)で示される
アミンとを、2.4.6−トリハロゲノ−S−トリアジ
ンに任意の順序でそれぞれを縮合させることにより得ら
れる。) and the following general formula (5)% formula% (5
) (wherein, Q has the above-mentioned meaning) or the following general formula (V) R1 starch H-N-Y, -Z, (V) (wherein, R,
, Y, and Z have the meanings given above. ) and 2.4.6-trihalogeno-S-triazine in any order.
2.4.6−トリハロゲノ−S−ト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r7o
乃至70℃でI)R2乃至9、更に三次を行う場合には
温11fjlO乃至100℃でpH2乃至7に調整しな
がら縮合させて一般式(I)で示される非対称ジオキサ
ジン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-trihalogeno-S-triazine, the order is not particularly limited,
Also, the reaction conditions are not particularly limited, but - secondly, temperature -
pH 2 to 9 at 10°C to 40°C, secondarily at temperature r7o
I) R2 to 9 at a temperature of 70°C to 70°C, and in the case of tertiary reaction, condensation at a temperature of 11fjlO to 100°C while adjusting the pH to 2 to 7 to obtain an asymmetric dioxazine compound represented by general formula (I) or a salt thereof. Can be done.
式偉)で表わされる非対称ジオキサジン中間体は、それ
自体公知の方法によって合成されるが、例えば以下の様
に合成することができる。The asymmetric dioxazine intermediate represented by the following formula can be synthesized by a method known per se. For example, it can be synthesized as follows.
相当するアニリン化合物とクロラニルを縮合することに
よって得られる下記−綴代(ロ)(式中、X、 R2、
Rs 、 Ra −Rs オヨヒW +、t ntr
記)意味を有する。)で示される非対称ジアニリド化合
物を、場合によっては酸化剤の存在下、理化させて一般
式(旬の非対称ジオキサジン中間体が得られる。The following - Tsuzuriyo (b) obtained by condensing the corresponding aniline compound and chloranil (in the formula, X, R2,
Rs, Ra -Rs Oyohi W +, t ntr
) have meaning. ) is chemically treated, optionally in the presence of an oxidizing agent, to obtain an asymmetric dioxazine intermediate of the general formula (2).
さらに、R4および/又は島が置換基を有していても良
い低級アルキル基である場合には対応するR4および/
又はRIIが水素である一般式(n)の非対称ジオキサ
ジン中間体または一般式(I)の非対称ジオキサジン化
合物を通常の方法でアルキル化することによっても得ら
れる。Furthermore, when R4 and/or the island is a lower alkyl group which may have a substituent, the corresponding R4 and/or
Alternatively, it can also be obtained by alkylating an asymmetric dioxazine intermediate of general formula (n) or an asymmetric dioxazine compound of general formula (I) in which RII is hydrogen by a conventional method.
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
プ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, staple 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、本来の染色温間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 or before the actual dyeing temperature has been reached, optionally in portions.
バジング法に従ってセルロースa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 a-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
ば重脩又はその他の酸結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
浴に通過させ、又はアルカリ性電I!i!!質含有パジ
ング液でオーバパジングし、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 carried out in one phase, e.g. by printing with a printing paste containing heavy or other acid binders and then steaming at 100-160°C, or in two phases, e.g. Printing with a neutral or slightly acidic printing paste and passing this through a hot electrolyte-containing alkaline bath or alkaline electrolyte I! i! ! It can be carried out by over-padding with a padding liquid containing quality, followed 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l殿粉
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(又は)分散剤
と併用して用いられる。The printing paste may optionally contain thickening agents or emulsifiers, such as, for example, sodium alginate or starch ether.
It is used in combination with conventional printing aids and/or dispersants, such as 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−ダ、ケイ酵ソ
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, silicate soda, and sodium trichloroacetate.
合成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℃の温間で行えるが、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8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 synthetic and natural polyamide and polyurethane fibers is carried out first by exhaustion under pH control from an acidic or slightly acidic dye bath, and then by changing to a neutral or even alkaline pH value for fixation. I can do it. Dyeing can usually be carried out at a warm 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 8 times the mole of aminobenzenesulfonic acid or aminonaphthalenesulfonic acid are used. Alternatively, for example addition products of stearylamine and ethylene oxide can 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・惜化洗潅性、耐汗性、耐層加水分解性及び耐ア
ルカリ性、更に良好な耐窄擦性と耐アイロン性を有する
。Particularly suitable for dyeing cellulose fiber materials, with good light fastness, sweat and sunlight resistance, and excellent moisture resistance, such as washing resistance, overwashing resistance, sweat resistance, and layer hydrolysis resistance. It has good alkali resistance, scratch resistance and iron 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 provides dyed products with stable quality that is less affected by fluctuations in dyeing temperature and dye bath ratio. 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.
実施例!
遊離酸の形で上記構造式で表わされる非対称ジオキサジ
ン中間体18部を水200部に入れ塩化シアヌル5.5
部と7ニリンーあ一ジスルホン酸7.6部を反応するこ
とで得られた縮合物を含む水溶1IJj200部を加え
、pH7〜9.10〜80℃で反応が終了するまで攪拌
した。さらに、アニリン−3−β−スルフ1−トエチル
スルホン8.4 mを加又、p H2〜6.80〜70
℃で反応が終了するまで攪拌することによって、遊離酸
の形で、下記構造式で表わされる非対称ジオキサジン化
合物を得た。Example! 18 parts of the asymmetric dioxazine intermediate represented by the above structural formula in free acid form are added to 200 parts of water and 5.5 parts of cyanuric chloride is added.
200 parts of an aqueous solution 1IJj containing a condensate obtained by reacting 1 part with 7.6 parts of 7-niline-1 disulfonic acid was added, and the mixture was stirred at pH 7-9.10-80°C until the reaction was completed. Furthermore, 8.4 m of aniline-3-β-sulf-1-toethyl sulfone was added, and the pH was adjusted to 2-6.80-70.
By stirring at °C until the reaction was completed, an asymmetric dioxazine compound represented by the following structural formula was obtained in the form of a free acid.
遊離酸の形で上記構造式で表わされる非対称ジオキサジ
ン中間体21.5部を水200部に入れ塩化シアヌル6
.6部を加えpH4〜7.0〜20℃で反応が終了する
まで攪拌した。その後、スルファニル酸5.2部を加え
、pH5〜7.10〜40℃で反応が終了するまで攪拌
した。さらに、アニリン−3−!−スルス1−トエチル
スルホン8.4部を加え、pH2〜G、80・〜70℃
で反応が終了するまで攪拌することによって、遊離酸の
形で、下記構造式で表わされる非対称ジオキサジン化合
物を得た。21.5 parts of the asymmetric dioxazine intermediate represented by the above structural formula in the form of free acid were added to 200 parts of water and mixed with cyanuric chloride 6.
.. 6 parts were added and stirred at pH 4-7.0-20°C until the reaction was completed. Thereafter, 5.2 parts of sulfanilic acid was added, and the mixture was stirred at pH 5-7.10-40° C. until the reaction was completed. Furthermore, aniline-3-! -Add 8.4 parts of sulus 1-toethylsulfone, pH 2~G, 80-70℃
By stirring until the reaction was completed, an asymmetric dioxazine compound represented by the following structural formula was obtained in the form of a free acid.
(λmax=6201m 但し水性媒体中 以下同じ
):bu、ti
(λmax嘗680nm)
実施例8
実施例2のスルファニル酸の代りに、アニリン−4−I
−スルフ1−トエチルスルホンを等モル用い、実施例2
と同様の方法で行うことによって、遊離酸の形で、下記
!IIt造式で表わされる非対六ジオキサジン化合物を
得た。(λmax = 6201 m, however, in an aqueous medium, the same applies below): bu, ti (λmax = 680 nm) Example 8 In place of sulfanilic acid in Example 2, aniline-4-I
Example 2 using equimolar amounts of -sulf-1-toethylsulfone
In the form of the free acid, by doing in a similar manner as below! An unpaired hexadioxazine compound represented by the formula IIt was obtained.
(λmax−m610nm)
実施例4
実施例1の非対称ジオキサジン中間体の代りに、遊離酸
の形で下記構造式
で表わされる非対称ジオキサジン中間体の等モルを用い
、実施例1と同様の方法で行う仁とによって、遊離酸の
形で、下記構造式で表わされる非対称ジオキサジン化合
物を得た。(λmax-m610 nm) Example 4 The same mole as in Example 1 was used except that in place of the asymmetric dioxazine intermediate in Example 1, equimolar amounts of the asymmetric dioxazine intermediate represented by the following structural formula in the form of free acid were used. An asymmetric dioxazine compound represented by the following structural formula was obtained in the form of a free acid.
(λmax= 620nm)
実施例5
実jllJ1のアニリン−2,6−ジスルホン酸の代り
に等モルの以下のアミンを用いて、実施例1と同様の操
作を行うことにより、対応する非対称ジオキサジン化合
物が得られた。(λmax = 620 nm) Example 5 The corresponding asymmetric dioxazine compound was prepared by carrying out the same procedure as in Example 1, using equimolar amounts of the following amine in place of aniline-2,6-disulfonic acid in JllJ1. Obtained.
(1) オルタニル酸
(2) メタニル酸
(8) スルファニル酸
(4) 1−アミノナフタレン−8,6−ジスルホン酸
(5)l−アミノナフタレン−4,6,8−トリスルホ
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−8,6,8−トリスル
ホン酸
(9)2−アミノナフタレン−4,8,8−トリスルホ
ン酸
not アニリン−2,4−ジスルホン酸αυ アニ
リン
α21N−メチルアニリン
0淘 N−エチルアニリン
α荀 m−トルイジン
C9p−トルイジン
C1m−クロルアニリン
C7) p−アニシジン
酩 p−アミノ安息香酸
a値 アンモニア
(4)エチルアミン
Qυ β−ヒドロキシエチルアミン
(ハ) β−アラニン
(ハ)タウリン
Q滲 N−メチルタウリン
実施例6
実m例2のスルファニル酸の代りに、等モルの、実施例
5の(1)〜C24)のアミンを用いて、実施例2と同
様の操作を行うことによって、対応する非対称ジオキサ
ジン化合物を得た。(1) Ortanilic acid (2) Metanilic acid (8) Sulfanilic acid (4) 1-aminonaphthalene-8,6-disulfonic acid (5) l-aminonaphthalene-4,6,8-trisulfonic acid (6) 2 -aminonaphthalene-1,5-disulfonic acid (7) 2-aminonaphthalene-4,8-disulfonic acid (8) 2-aminonaphthalene-8,6,8-trisulfonic acid (9) 2-aminonaphthalene-4 ,8,8-trisulfonic acid not Aniline-2,4-disulfonic acid αυ Aniline α21N-Methylaniline 0 N-Ethylaniline α m-Toluidine C9p-Toluidine C1m-Chloraniline C7) p-anisidine p-amino Benzoic acid a value Ammonia (4) Ethylamine Qυ β-Hydroxyethylamine (C) β-Alanine (C) Taurine Q N-Methyl taurine Example 6 In place of sulfanilic acid in Example 2, equimolar Example The corresponding asymmetric dioxazine compound was obtained by carrying out the same operation as in Example 2 using the amines (1) to C24) of Example 5.
実施例7
実施例1および実権例2のアニリン−8−β−スルフア
ートエチルスルホンの代りに、等モルの以下のアミンを
用いて、実施例1または実施例2と同様の方法で行うこ
とによって、対応する非対称ジオキサジン化合物を得た
。Example 7 In place of aniline-8-β-sulfatoethyl sulfone in Example 1 and Actual Example 2, equimolar amounts of the following amines were used to carry out the same procedure as in Example 1 or Example 2. The corresponding asymmetric dioxazine compound was obtained.
実施例8
実施例1および実施例2において用いた非対称ジオキサ
ジン中間体の代りに等モルの遊離酸の形で下記構造式で
表わされる非対称ジオキサジン中間体を用いることによ
って、対応する非対称ジオキサジン化合物を得た。Example 8 The corresponding asymmetric dioxazine compounds were obtained by replacing the asymmetric dioxazine intermediates used in Examples 1 and 2 with equimolar amounts of the asymmetric dioxazine intermediate represented by the following structural formula in the form of the free acid. Ta.
実権例9
実施例5〜実施例7で用いた非対称ジオキサジン中間体
の代りに、実施例8で用いた非対称ジオキサジン中間体
の等モルを用いることによって、対応する非対称ジオ・
キサジン化合物が得られた。Practical Example 9 By replacing the asymmetric dioxazine intermediates used in Examples 5 to 7 with equimolar amounts of the asymmetric dioxazine intermediates used in Example 8, the corresponding asymmetric dioxazine intermediates were obtained.
A xazine compound was obtained.
実施例10
実施例1で得られた非対称ジオキサジン化合物35部を
水200部中に入れ、5部のエチレンクロルヒドリンを
添加し、1)H6〜?、40〜90℃で反応が終了する
まで攪拌し、遊離酸の形で、下記構造式で表わされる非
対称ジオキサジン化合物を得た。Example 10 35 parts of the asymmetric dioxazine compound obtained in Example 1 were placed in 200 parts of water, 5 parts of ethylene chlorohydrin was added, and 1) H6~? The mixture was stirred at 40 to 90° C. until the reaction was completed to obtain an asymmetric dioxazine compound represented by the following structural formula in the form of a free acid.
実施例11
実施例1〜10で得られた各々の非対称ジオキサジン化
合物0.1.0.8及び0.6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。水洗、ソーピン
グ、水洗そして乾燥を行ない、諸堅牢度に優れ、良好な
ビルドアツプ性を有する帯赤味青色の染色物が得られた
。Example 11 Each of the asymmetric dioxazine compounds 0.1, 0.8 and 0.6 obtained in Examples 1 to 10 was dissolved in 200 parts of water, 10 parts of Glauber's salt and 10 parts of cotton were added, and the mixture was heated to 60°C. The temperature was raised, 4 parts of soda carbonate was added, and dyeing was carried out for 1 hour. After washing with water, soaping, rinsing with water and drying, a reddish blue dyed product having excellent fastness and good build-up properties was obtained.
実施例12
実施例1〜10で得られた非対杯ジオキサジン化合物の
それぞれを用いて、以下の組成をもつ色糊を作った。Example 12 A colored paste having the following composition was prepared using each of the non-copper dioxazine compounds obtained in Examples 1 to 10.
非対称ジオキサジン化合物 5部尿素
5部アルギン酸ソーダ(5
%)元糊 50部熱湯
26部重曹 2部
バランス 18部この色糊を
シルケット加工綿ブロード上に印捺し、中間乾燥後、1
00℃で5分間スチー主ングを行い、崗洗い、ソーピン
グ、場洗いそして乾燥した。得られた染色物は、諸堅牢
度に優れ、良好なビルドアツプ性を有していた。Asymmetric dioxazine compound 5-part urea
5 parts Sodium alginate (5 parts
%) Motonori 50 parts boiling water
26 parts baking soda 2 parts balance 18 parts This color paste is printed on mercerized cotton broadcloth, and after intermediate drying, 1
Steaming was performed at 00°C for 5 minutes, followed by washing, soaping, washing in place, and drying. The obtained dyed product was excellent in various fastnesses and had good build-up properties.
(以下余白)(Margin below)
Claims (6)
肪族又は芳香族の架橋基を、Qは置換されていてもよい
アミノ基又は式▲数式、化学式、表等があります▼で示
され る基を、R_1、R_2、R_3、R_4、R_5およ
びR_6は互いに独立に水素又は置換基を有していても
よい低級アルキル基を、Y_1およびY_2は互いに独
立に、置換基を有していてもよいアルキレン、フェニレ
ン又はナフチレン基を、Z_1およびZ_2は互いに独
立に、−SO_2CH=CH_2又は−SO_2CH_
2CH_2Z′(Z′はアルカリの作用で脱離する基を
表わす。)を表わす。〕で示される非対称ジオキサジン
化合物。(1) In the form of a free acid, there are the following general formulas ▲ mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, An optionally substituted amino group or a group represented by the formula ▲ There are mathematical formulas, chemical formulas, tables, etc. Y_1 and Y_2 independently represent an optionally substituted alkylene, phenylene or naphthylene group; Z_1 and Z_2 independently represent -SO_2CH=CH_2 or -SO_2CH_
2CH_2Z'(Z' represents a group that is eliminated by the action of an alkali). ] An asymmetric dioxazine compound represented by
〜2個のスルホ基を有したフェニレンである請求項1に
記載の化合物。(2) W is ethylene, propylene, phenylene or 1
2. The compound according to claim 1, which is phenylene having ~2 sulfo groups.
2に記載の化合物。(3) The compound according to claim 1 or 2, wherein R_2 and R_3 are hydrogen.
いずれかに記載の化合物。(4) The compound according to any one of claims 1 to 8, wherein R_4 and R_5 are hydrogen.
かに記載の化合物。(5) The compound according to any one of claims 1 to 4, wherein X is chlorine or bromine.
ジン化合物を用いることを特徴とする繊維材料を染色又
は捺染する方法。(6) A method for dyeing or printing a fiber material, which comprises using the asymmetric dioxazine compound according to any one of claims 1 to 5.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP1031496A JP2671477B2 (en) | 1989-02-09 | 1989-02-09 | Asymmetric dioxazine compound and method for dyeing or printing fiber material using the same |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP1031496A JP2671477B2 (en) | 1989-02-09 | 1989-02-09 | Asymmetric dioxazine compound and method for dyeing or printing fiber material using the same |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH02209970A true JPH02209970A (en) | 1990-08-21 |
JP2671477B2 JP2671477B2 (en) | 1997-10-29 |
Family
ID=12332856
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP1031496A Expired - Lifetime JP2671477B2 (en) | 1989-02-09 | 1989-02-09 | Asymmetric dioxazine compound and method for dyeing or printing fiber material using the same |
Country Status (1)
Country | Link |
---|---|
JP (1) | JP2671477B2 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6592634B1 (en) * | 1999-03-15 | 2003-07-15 | Ciba Specialty Chemicals Corporation | Reactive dyes, processes for their preparation and their use |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6375066A (en) * | 1986-09-12 | 1988-04-05 | チバーガイギ アクチエンゲゼルシヤフト | Dioxazine reactive dye, and its production and use |
-
1989
- 1989-02-09 JP JP1031496A patent/JP2671477B2/en not_active Expired - Lifetime
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6375066A (en) * | 1986-09-12 | 1988-04-05 | チバーガイギ アクチエンゲゼルシヤフト | Dioxazine reactive dye, and its production and use |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6592634B1 (en) * | 1999-03-15 | 2003-07-15 | Ciba Specialty Chemicals Corporation | Reactive dyes, processes for their preparation and their use |
Also Published As
Publication number | Publication date |
---|---|
JP2671477B2 (en) | 1997-10-29 |
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