JPH03263469A - Bisazo compound and method for dyeing or printing fiber material using same composition - Google Patents
Bisazo compound and method for dyeing or printing fiber material using same compositionInfo
- Publication number
- JPH03263469A JPH03263469A JP2063714A JP6371490A JPH03263469A JP H03263469 A JPH03263469 A JP H03263469A JP 2063714 A JP2063714 A JP 2063714A JP 6371490 A JP6371490 A JP 6371490A JP H03263469 A JPH03263469 A JP H03263469A
- Authority
- JP
- Japan
- Prior art keywords
- group
- formula
- sulfo
- dyeing
- hydroxy
- 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 Bisazo compound Chemical class 0.000 title claims abstract description 41
- 238000004043 dyeing Methods 0.000 title claims abstract description 20
- 239000002657 fibrous material Substances 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 6
- 239000000203 mixture Substances 0.000 title description 3
- 239000002253 acid Substances 0.000 claims abstract description 43
- 150000001875 compounds Chemical class 0.000 claims abstract description 22
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims abstract description 15
- 125000004957 naphthylene group Chemical group 0.000 claims abstract description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 8
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims abstract description 7
- 239000003513 alkali Substances 0.000 claims abstract description 5
- 230000009471 action Effects 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 4
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 239000011737 fluorine Chemical group 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 125000005650 substituted phenylene group Chemical group 0.000 claims 1
- 239000000835 fiber Substances 0.000 abstract description 11
- 239000000463 material Substances 0.000 abstract description 10
- 229920003043 Cellulose fiber Polymers 0.000 abstract description 4
- 239000004952 Polyamide Substances 0.000 abstract description 4
- 229920002647 polyamide Polymers 0.000 abstract description 4
- 150000001412 amines Chemical class 0.000 abstract description 3
- 239000010985 leather Substances 0.000 abstract description 3
- 229920006306 polyurethane fiber Polymers 0.000 abstract description 3
- 235000002639 sodium chloride Nutrition 0.000 description 8
- 239000000975 dye Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 5
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000010025 steaming Methods 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
- 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
- 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
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical group 0.000 description 2
- 125000005521 carbonamide group Chemical group 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 2
- 150000008049 diazo compounds Chemical class 0.000 description 2
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical group C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000003792 electrolyte Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens 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
- 159000000001 potassium salts Chemical class 0.000 description 2
- 239000000985 reactive dye Substances 0.000 description 2
- 239000000661 sodium alginate Substances 0.000 description 2
- 235000010413 sodium alginate Nutrition 0.000 description 2
- 229940005550 sodium alginate Drugs 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 210000004243 sweat Anatomy 0.000 description 2
- 239000004753 textile Substances 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
- 238000005406 washing Methods 0.000 description 2
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 1
- SEPPVOUBHWNCAW-FNORWQNLSA-N (E)-4-oxonon-2-enal Chemical compound CCCCCC(=O)\C=C\C=O SEPPVOUBHWNCAW-FNORWQNLSA-N 0.000 description 1
- JVMSQRAXNZPDHF-UHFFFAOYSA-N 2,4-diaminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C(N)=C1 JVMSQRAXNZPDHF-UHFFFAOYSA-N 0.000 description 1
- 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
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 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
- AVVFSYNLQVDQID-UHFFFAOYSA-N 2-phenylnaphthalen-1-ol Chemical compound C1=CC2=CC=CC=C2C(O)=C1C1=CC=CC=C1 AVVFSYNLQVDQID-UHFFFAOYSA-N 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
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 1
- LLBZPESJRQGYMB-UHFFFAOYSA-N 4-one Natural products O1C(C(=O)CC)CC(C)C11C2(C)CCC(C3(C)C(C(C)(CO)C(OC4C(C(O)C(O)C(COC5C(C(O)C(O)CO5)OC5C(C(OC6C(C(O)C(O)C(CO)O6)O)C(O)C(CO)O5)OC5C(C(O)C(O)C(C)O5)O)O4)O)CC3)CC3)=C3C2(C)CC1 LLBZPESJRQGYMB-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 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
- 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
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 241000545744 Hirudinea Species 0.000 description 1
- 241001465754 Metazoa Species 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
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000220317 Rosa Species 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
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000001246 bromo group Chemical group Br* 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
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 235000005607 chanvre indien Nutrition 0.000 description 1
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 1
- 238000004040 coloring Methods 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
- QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 description 1
- VMKJWLXVLHBJNK-UHFFFAOYSA-N cyanuric fluoride Chemical compound FC1=NC(F)=NC(F)=N1 VMKJWLXVLHBJNK-UHFFFAOYSA-N 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 238000007598 dipping method Methods 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
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 238000010016 exhaust dyeing Methods 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 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
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000010409 ironing Methods 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical group CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 150000007522 mineralic acids Chemical class 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
- 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
- 229940072033 potash Drugs 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 235000007686 potassium Nutrition 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 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
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
- 235000019254 sodium formate Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 229940080313 sodium starch Drugs 0.000 description 1
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Landscapes
- Coloring (AREA)
Abstract
Description
【発明の詳細な説明】
〈産業上の利用分野〉
本発明はヒドロキシル基及び／又はアミド基を含有する
材料、特にセ／ｌ／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、耐光堅牢かつ
耐湿潤堅牢な紺色染色を可能にする改良された化合物、
並びにその適用に関する。Detailed Description of the Invention <Industrial Application Field> The present invention is applicable to materials containing hydroxyl groups and/or amide groups, in particular se/l/loin fibers, natural or synthetic polyamide fibers, polyurethane fibers, leather, etc. is an improved compound suitable for dyeing and printing those blended fibers, which enables light-fast and wet-fast dark blue dyeing,
and its application.
〈従来の技術〉
同一４子内にトリアジニル基および複数個のビニルスル
ホン系反応基を有するビスアゾ化合物としては、特開昭
６８−１１８８７６公報において公知であるが、染色性
能面、例えばビルドアツプ性において不充分であ漫、更
にレベルアッソ°が望まれ又いる。<Prior art> A bisazo compound having a triazinyl group and a plurality of vinyl sulfone reactive groups within the same quadrupole is known from Japanese Patent Application Laid-Open No. 118876/1987, but it is not good in terms of dyeing performance, for example, build-up property. It is sufficient and ample, and even more level is desired.
〈発明が解決しようとする課題〉
従来、種々の反応染料は繊維材料の葉色及び捺染の分野
に広く使用され１いる。し２かし現在の技術水準は、特
定の染色法に対する適性に関する高い要求水準ならびに
染色物の堅牢性に関する吸水の高度化の点から満足すべ
きものではない。<Problems to be Solved by the Invention> Conventionally, various reactive dyes have been widely used in the fields of leaf coloring and printing of textile materials1. However, the current state of the art is not satisfactory in terms of high requirements regarding suitability for specific dyeing methods and high water absorption with regard to the fastness of dyed products.
前記した公知の反応染料は、溶解性、染色性能（例えば
ビルドアツプ性等）及び堅牢性の而で不十分であり、更
に改良された染料の提供が強く望まれている。The above-mentioned known reactive dyes are insufficient in solubility, dyeing performance (for example, build-up properties, etc.), and fastness, and there is a strong desire to provide further improved dyes.
ビルドアツプ性に模れることの重要性は：、染色方法の
経済性に対する要求レベルがますます高くガってきてい
る今日、極めて重要な要素で、ろる。The importance of being able to imitate build-up properties: This is an extremely important element in today's world, where the demand for economical dyeing methods is becoming higher and higher.
本発明者らは、上述の公知染料の欠点を「ｙ良し、さら
に染料に対して要求される要件を広く満足できる新規な
化合物を見い出す目的で鋭意検討し２だ結果、本発明を
完成し、た。The present inventors have intensively investigated the drawbacks of the above-mentioned known dyes with the aim of finding a new compound that has good properties and can broadly satisfy the requirements required for dyes.As a result, the present invention has been completed. Ta.
〈課萌を解決する為の手段〉
本発明は、下記一般弐（Ｉ）
〔式中、Ｘは、塩素まだはフッ素を、Ｚｌ およヒＺ
ｔ位、互イＫ 独立Ｋ −８Ｏ２ＣＨ＝ＣＨ２ｔ ７’
ＣバーＳＯｇＣＨｇＣＨ２Ｚ’ を表し、２′はアルカ
リの作用で脱離する基を表す。Ａは、置換基されていて
もよいフヱニレンまたはプフチレン基を表す。Ｂは、下
式カルボキシおよびスルホの群から選ばれる、１又は２
個の置換基により置換されていてもよいフェニレン基、
またはスルホによって置換されていてもよいナフチレン
基を表す。損およびＲ２は、互いに独立に水素又は置換
されていてもよいアルキμ基を表す。Ｘｉ及びＸ！は、
一方がＮＨｍ基で、他方がＯＨ基を表す。〕で示される
ビスアゾ化合物およびそれを用いることを特徴とする繊
維材料を染色または捺染する方法を提供するものである
。<Means for solving the problem> The present invention provides the following general 2 (I) [wherein, X is chlorine or fluorine, Zl and HZ]
t position, Mutual K Independent K -8O2CH=CH2t 7'
C bar represents SOgCHgCH2Z', and 2' represents a group that is eliminated by the action of an alkali. A represents an optionally substituted phenylene or pufthylene group. B is 1 or 2 selected from the group of carboxy and sulfo of the formula
a phenylene group optionally substituted with substituents;
or represents a naphthylene group optionally substituted with sulfo. and R2 independently represent hydrogen or an optionally substituted alkyl μ group. Xi and X! teeth,
One represents an NHm group and the other represents an OH group. The present invention provides a bisazo compound represented by the following and a method for dyeing or printing a fiber material using the bisazo compound.
前記一般弐（１）で示されるビスアゾ化合物のうち染色
性能上、好ましくはＸｌがＯＲ基でＸ２がＮＨ！基であ
る遊離酸の形で丁記一般式（１）（式中、＊印は、アゾ
基に接続する結合を、Ｒｓは水素、メチル基またはスル
ホ基を表す。）で示すしる基を表す。Ｉ）は、アルキル
、アルコキシ、（５）
〔式中、ｚｌ、Ｚｇ、Ａ、Ｂ、Ｄ、Ｘ、Ｒ１ｉｔびＲ１
は、前記の意味を有する。〕 で示されるビスアゾ化合
物を挙げることができる。Of the bisazo compounds represented by General 2 (1) above, from the viewpoint of dyeing performance, preferably Xl is an OR group and X2 is NH! A group represented by the general formula (1) (in the formula, the * mark represents a bond connected to an azo group, and Rs represents hydrogen, a methyl group, or a sulfo group) in the form of a free acid group. represent. I) is alkyl, alkoxy, (5) [wherein zl, Zg, A, B, D, X, R1it and R1
has the meaning given above. ] Bisazo compounds represented by these can be mentioned.
一般弐（１）において、Ａで表されるフエニレ（６）
ンおよびナフチレンとしては、好ましくはメチル、エチ
ル、メトキシ、エトキシ、クロロ、ブロモ及びスルホの
群から選ばれる、１又は２個の置換基によシ置換されて
いてもよいフェニレン又は、スルホで置換されていても
よいナフチレンが例示され、例えば、
（式中、＊＊で示した結合は、−Ｎ−基に通じている結
合を意味する。）
などが例示され、好ましくは、
等を挙げることができろ。In General 2 (1), phenylenes (6) and naphthylenes represented by A preferably contain one or two substituents selected from the group of methyl, ethyl, methoxy, ethoxy, chloro, bromo and sulfo. Examples include phenylene which may be substituted with , or naphthylene which may be substituted with sulfo, such as (wherein, the bond shown with ** means a bond that connects to the -N- group). ) etc., preferably, etc.
Ｂで示される基としては、
メトキシ、エトキシなどのＣＩ −Ｃ４アルコキシ、力
ρボキシ及びスルホの群から選ばれる、１又は２個の置
換基によシ置換されていてもよいフェニレン又は、スル
ホで置換されていてもよいナフチレンであυ、例えば、
（式中、＊で示した結合は前記の意味を有する。）など
が例示され、好ましくは、
等を挙げることができる。The group represented by B is phenylene optionally substituted with one or two substituents selected from the group of CI-C4 alkoxy such as methoxy and ethoxy, ρ-boxy and sulfo, or sulfo. Naphthylene which may be substituted, for example, (in the formula, the bond indicated by * has the above-mentioned meaning) is exemplified, and preferably the following can be mentioned.
キ
Ｄは、エチル、メチｐなどのＣ１〜Ｃ４ア／Ｉ／ｇル、
（９）
（１０）
５Ｏ８Ｈ
（式中、＊＊＊で示した結合は、もう一方のＮ−Ｎ−基
に通じている結合を意味する。）等をあげることができ
る。Ki D is C1-C4 a/I/g such as ethyl, methylp, etc.
(9) (10) 5O8H (In the formula, the bond indicated by *** means a bond communicating with the other N-N- group.).
中でも、アゾ基のオルシソ位にスルホ基を有するものが
好ましく、例えば、
等をあげることができる。Among these, those having a sulfo group at the orciso position of the azo group are preferred, and examples thereof include the following.
Ｚ′で示されるアルカリの作用で脱離する基としてハ、
例えば、硫酸エステル、チオ硫酸エステル、リン酸エス
テル、酢酸エステル、ハロゲン等力これに該当し、中で
も硫酸エステルが好まＲ２い。As a group that is eliminated by the action of an alkali represented by Z', C,
For example, sulfuric acid ester, thiosulfuric acid ester, phosphoric acid ester, acetic ester, halogen, etc. fall under this category, and among these, sulfuric acid ester is preferred.
Ｒ１およびＲ２で示される置換され−Ｃいでもよいアル
キルとし、では、 Ｃ＋〜Ｃ４０アルギルが好ｌしく、
置換されていてもよい基としては、ヒドロキシ、シアノ
、アルコキシ、ハロゲン、カルバモイル、カルボキシ、
アルコキシカルボニル、アルキルカルボニルオキシ、ス
ルホおよびスルフ１モイルが好ましい。R1 and R2 are optionally substituted -C alkyl, preferably C+ to C40 argyl;
Examples of optionally substituted groups include hydroxy, cyano, alkoxy, halogen, carbamoyl, carboxy,
Preferred are alkoxycarbonyl, alkylcarbonyloxy, sulfo and sulfmoyl.
好ましいＲ１およびル２とし７ては、４Ｍｌえば、水素
、メチル、エチル、ｎ−プロピル、１ｓｏ−プロピル、
ｎ−ブチル、１８０−ブチル、５ｅｅ−ブチル、２−ヒ
ドロキシエチル、２−ヒドロキシゾロピ、Ｖ、３−ヒド
ロキシプロピル、２−ヒドロキシフ＋〜、３−ヒドロギ
シブチル１．４−ヒドロギシグチル、２，８−ジヒドロ
キシプロピル、８．４−ジヒドロキシブチル、シアノメ
チル、２−シアノメチル、８−シアノプロピル、メトキ
シエチル、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、３−エトキシ
プロピル、２−ヒドロキシ−ａ−メトキシプロピル、ク
ロロエチルノ、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、３−グロモグ【Ｉ
ヒル、４−クロロブチル、４−プロ七ブナｐ、カルボキ
シメチル、２−カルボキシプロピル、８−カルボキシプ
ロピル、４−カルボキシブチル、１．２−ジカルボギン
エチル、カルバモイルメチル、２−カルバモイルエチル
、８−カッ１／ハ モ イ ル゛ソ０ロ ピル、 ４
−一 刀 ！レバ モ イ ル’７”ｆ／１７、メトキ
シカルホニルメチル、エトキシ力ルポニルノチノ１／、
２−メトギシ力ルポニルエチル、２−エトギシ力ルポニ
ルエチル、３−メトキシ力ルボニ／ｌ／プロピル、３−
エトキシカルボニルプロビル、４−メトＡもジカルボニ
ルブーブール、４−エトＡシカルボユ；ルグチル、メチ
ル力ルボニｐオキシメチル、エチル力ルボニ／ｖオギシ
メチル、２−メチルカルボ＝ｙオキシエチル、２−エチ
ルカルボニルオキシューデル、３− メチル【′カルボ
ニルオキシプロピＡ／、３−エチルカＭボコ；ルオギシ
ブロビル、４−メチル力ルボニルオＡシフ゛チ／Ｌ・、
４−エチルカルボニル号ギシブヂル、スフＬホメチル、
２−ス）Ｖ弔エチ（１３）
ル、３−スルホ１ロビル、４−スルホブチμ、ス〜ファ
モイｙメチル、２−スルファモイルエチル、３−スルフ
ァモイルプロピル、４−スルファモイルグチμをあける
ことができる。中でも、水素、メチ／ｌ’またはエチル
が好ましく、特にＲ１が水素、メチ／Ｌ’またはエチル
であり、Ｒｇが水素である場合が好ましい。Preferred examples of R1 and R2 include 4Ml, such as hydrogen, methyl, ethyl, n-propyl, 1so-propyl,
n-butyl, 180-butyl, 5ee-butyl, 2-hydroxyethyl, 2-hydroxyzolopi, V, 3-hydroxypropyl, 2-hydroxyph+~, 3-hydroxybutyl 1.4-hydroxybutyl, 2,8- Dihydroxypropyl, 8.4-dihydroxybutyl, cyanomethyl, 2-cyanomethyl, 8-cyanopropyl, methoxyethyl, ethoxymethyl, 2-methoxyethyl, 2-
Ethoxyethyl, 8-methoxypropyl, 3-ethoxypropyl, 2-hydroxy-a-methoxypropyl, chloroethyl, bromomethyl, 2-chloroethyl, 2-
Bromoethyl, 8-chloropropyl, 3-gromog [I
leech, 4-chlorobutyl, 4-proseptobunap, carboxymethyl, 2-carboxypropyl, 8-carboxypropyl, 4-carboxybutyl, 1,2-dicarbogynethyl, carbamoylmethyl, 2-carbamoylethyl, 8- Kak1/Hamo Iru Soro Pill, 4
-One sword! Rebamoyl'7"f/17, methoxycarbonylmethyl, ethoxylponylnotino 1/,
2-Methoxyluponylethyl, 2-ethoxyluponylethyl, 3-methoxyluponylethyl, 3-
Ethoxycarbonylprobyl, 4-MethoA also dicarbonylboubour, 4-EthoA cycarboy; Lugutyl, Methyloxymethyl, Ethyloxymethyl, 2-Methylcarboxyoxyethyl, 2-ethylcarbonyloxymethyl del, 3-methyl['carbonyloxypropylene A/, 3-ethylkaMboko;
4-ethylcarbonyl No. Gishibudil, Sufu L-phomethyl,
2-S) V ethyl(13), 3-sulfo1rovir, 4-sulfobutyl, methyl, 2-sulfamoylethyl, 3-sulfamoylpropyl, 4-sulfamoylgutiμ can be opened. Among these, hydrogen, methyl/l' or ethyl is preferred, and it is particularly preferred that R1 is hydrogen, meth/L' or ethyl and Rg is hydrogen.
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環、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 salts and alkaline earth metal rings, especially the soda salts, potassium salts, lithium salts.
本発明化合物は、例えば次の様にして製造することがで
きる。下記一般弐（ＩＩＩ）
〔式中、Ｂ％ＤＳＲｖ、ＸＩ、Ｘ２及びｚｌは前記の意
味を有する。」
で示される化合物と、次紀一般式（ＩＶ）（１４）
〔式中、Ｒ１、Ａ及びｚ２は前記の意味を有する。〕で
示さｎるアミンのいずれかとを、２，４．６−ドリハロ
ゲノーＳ−）リアジンに任意の順序で縮合させることに
より、一般弐（１）の化合物を得ることができる。The compound of the present invention can be produced, for example, in the following manner. The following general 2 (III) [wherein B%DSRv, XI, X2 and zl have the above-mentioned meanings. '' and the following general formula (IV) (14) [wherein R1, A and z2 have the above-mentioned meanings. The compound of general 2 (1) can be obtained by condensing any of the amines represented by n with 2,4,6-dolyhalogeno S-) riazine in any order.
２．４．６−）リハロゲノ−３）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、釜
た反応条件も特に制限されないが、−次的には温度−１
０℃乃至４０℃でＩ）Ｒ２乃至９、二次的には温度０乃
至７０℃でｐＨ２乃至９に調整しながら組合させて一般
式（１）で示される化合物又はその塩を得ることができ
る。2.4.6-) Rehalogeno-3) In the condensation reaction with riazine, the order is not particularly limited, nor are the reaction conditions used in the pot.
A compound represented by general formula (1) or a salt thereof can be obtained by combining I) R2 to 9 at 0°C to 40°C, and secondarily while adjusting the pH to 2 to 9 at a temperature of 0 to 70°C. .
原料の２．４．６−ドリハロゲノー８−）リアジンとし
ては、塩化Ｖアヌρまたはフッ化シアヌρが用いられる
。As the raw material 2.4.6-dolyhalogeno8-)riazine, V-chloride ρ or cyanine fluoride ρ is used.
本発明における色素母体〔前記一般弐（ｌＩＩ）におけ
るビニルスルホン系ｙ応基が水素原子である化合物〕と
して、例えば、
１〜ヒドロキシ−２−（１’−スルホナフト−２′−イ
ルアゾ）−７−（５’−アミノ−２′−スμホフエニル
アゾ）−８−アミノナフタレン−３，６−ジヌ〜ホン酸
、
１〜ヒドロキシ−２−（１’−スルホナフト−２′−イ
ルアゾ）−７−（５’−アミノ−２′−スルホフェニル
アゾ）−８−アミノナフタレン−８，５−ジスルホン酸
、
１〜ヒドロキシ−２−（５’−アミノ−２′スρホフヱ
ニμアゾ）−７−（１’−スルホナフト−２１〜イμア
ゾ）−８−アミノナフタレン−８，６−ジスルホン酸、
１〜ヒドロキシ−２−（５’−アミノ−２′スルホフエ
ニｐアゾ）−７−（１’−スルホナフト−２ｐ−イルア
ゾ）−８−アミノナフタレン−８，５−ジスルホン酸、
１〜ヒドロキシ−２−（１’−スルホナフト−２１〜イ
〃アゾ）−７−（５’−アミノ−２′４′−ジスルホフ
ェニルアゾ）−８−アミツナフタノン−８，６−ジスρ
ホン酸、
１〜ヒドロキシ−２−（ｉ’−スルホナフト−２′−イ
ルアゾ）−７−（５’−アミノ−２′４＃−ジスルホフ
ェニルアゾ）−８−アミノナフタレン−８，５−ジスル
ホン酸、
１〜ヒドロキシ−２−（５’−アミノ−２′４′−ジス
ルホフェニルアゾ）−７−（１’−スルホナフト−２１
〜イμアゾ）−８−アミノナフタレン−８，６−ジスμ
ホン酸、
１〜ヒドロキシ−２−（５’−アミノ−２′４′−ジス
ルホフェニルアゾ）−７−（１’−スルホナフト−２１
〜イルアゾ）−８−アミノナフタレン−３，５−ジスル
ホン酸、
１〜ヒドロキシ−２−（１’、７’ −ジスルホナフト
−２′−イルアゾ）−７−（５’−アミノ−２′−スｐ
ホフェニμアゾ）−８−７ミノナフタレンー８，６−ジ
スμホン酸、
１〜ヒドロキシ−２−（５’−アミノ−２′−スルホフ
ェニμアゾ）−７−（１’ 、７’−ジスμホフェニ
ルナフトー２１〜イ〃アゾン−８−アミノナフタレン−
８，６−ジス〃ホン酸、（１７）
ｌ−ヒドロキシ−２−（５’−アミノ−２′−スルホフ
ェニ〃アゾ）−７−（６’−スルホナフト−２１〜イル
アゾ）−８−アミノナフタレン−８，６−ジスρホン酸
、
ｌ−ヒドロキシ−２−（５’−アミノ−２′スμホフエ
ニルアゾ）−７−（８’−ヌ〃ホナフトー２１〜イルア
ゾ）−８−アミノナフタレン−８，６−ジスルホン酸、
１〜ヒドロキシ−２−（５’−アミノ−２′スｐホフエ
ニｐアゾ）−７−（６’−スルホナフト−２１〜イルア
ゾ）−８−アミノナフタレン−８，５−ジスルホン酸、
１〜ヒドロキシ−２−（１’−スルホナフト−２′−イ
ルアゾ）−７−（４’−アミノ−２′−ス〜ホフエニル
アゾ）−８−アミノナフタレン−８，６−ジスルホン酸
、
１〜ヒドロキシ−２−（１′−スルホナフト−２′−イ
ルアゾ）−７−（４’−アミノ−２’、５’−ジスルホ
フェニルアゾ）−８−アミノナフタレン−８，６−ジス
ｐホン酸、
（１８）
１〜ヒドロキシ〜 ２−（１〜スルホナフト２′−イル
アゾ）−７−（４’−アミノ−２５５′−ジスルホフェ
ニルアゾ）−８−アミノナフタレン−３，５−ジスルホ
ン酸、
１〜ヒドロキシ−２−（１’−スルホ−５′アミノメチ
ルナフト−２′−イルアゾ） −７−（２１〜スルホフ
ェニルアゾ）−８−アミノナフタレン−３，６−ジスル
ホン酸、
１〜ヒドロへシー ｌ−（２’ −スルホフェニルアゾ
）−７−（１’−スル小−５′−アミノメチルナフト−
２１〜イＡ／アゾ）−８−アミノナフタレン−３，６−
ジスルホン酸、
Ｉ−ヒドロキシ−２−（１，’−ス〜ホー５′アミノメ
チルナフト−・２′・−イルアゾ）・〜７−（１′−ス
ルホノーフトー２′−イルアゾ）−８−７ミノナフタレ
ンー３．６−ジスルホン酸、１〜ヒドロキシ・−２−（
］’ −スルホナフト−２′−イルアゾ） −７−（］
、、 ］’−スルホ−５′アミノメチルナフト−２１〜
イルアゾ）−８−アミノナフタレン−８，６−ジスルホ
ン酸、１〜ヒドロキシ−２−（１’ 、７’ 〜ジ
スルホー５ ’−アミツメデルナフトー２′〜イ／１／
アゾ）−７−（２’−スルホフェニルアゾ）−８−アミ
ノナフタレン−８，６−ジスルホン酸、１〜ヒドロキシ
−２−（２’−スルホフェー′：′ルアゾ）−７−（１
’ 、７’−ジスルホ−５１〜アミノメチルナフト−２
′〜イｐアゾ）−８−アミノナフタレン−８，６−ジス
ルホン酸、１〜ヒドロヤシ−２−（５′ −アミノメチ
ル４′−メチ／Ｌ／ ２１〜スルホフェニルアゾ）・
−７−（１′−スルホナフト−２′−イルアゾ）−８−
７ミノナフタレンー８．６−ジスルホン酸、１〜ヒドロ
キシ−２−（１，’−スルホナフ） −２１〜イルアゾ
）−７−（５’−アミノメチル−４１〜メチ／Ｌ／
２ ＃−スルホフＸ二〜アゾ）−８−アミノナフタレン
−８，６−ジスルホン酸、１〜ヒドロキシ−２−（２’
−スルホフェニル”アゾ）−７−（５’−アミノ−２
′−スルホフェニルアゾ）−８−アミノナフタレン−８
，６−ジスｐホン酸、
■−ヒドロキシ〜１〜（５’−アミノ−２′ヌ、レホフ
エニルアゾ）−７−（２’−ヌμホフエニルアソ゛）−
８−アミノプープタレン′−８．Ｇ−ジスルホン酸、
１〜ヒドロキシ−２（２１〜スルホブＸニルアゾ）
７ （５’−アミノ−２’ 、４’−ジスルホフェ
ニル・アゾ＞−Ｓ、−アミノナフタレン−３，６−ジス
ルホン酸、
１〜ビト′ロギシー２−（１’−スルホナフト−２′−
イルアゾ）−’１〜（１’、７’−ジスルホ５′−アミ
ノメチルナフト−２１〜イルアゾ）−８−アミノナフタ
レン−３，６−ジスルホン酸、１〜ヒドロキシ−２−（
１’−スルホナフト−２′−イルアゾ）−７−（５’−
アミノー４′−メチル−２′−スルホフェニルアゾ）−
８−アミノナフタレン−８，６−ジスルホン酸、
１〜ヒドロＡ゛シー ２−（５’ −アミノ−２′メル
ホフ、ニルアゾ）−７−フＪニルアゾ−８−アミノナフ
タレン−８，６−ジスルホン酸、１〜ヒドロＡ゛シー２
〜 （５′−アミノ−２′（２１）
４′−ジスルホフェニルアゾ）−７−フエニ／ｌ／アゾ
８−アミノナフタレン−８１，６−ジスルホン酸などが
挙げられる。Examples of the dye matrix in the present invention [a compound in which the vinyl sulfone y-reactive group in the general II (lII) is a hydrogen atom] include 1-hydroxy-2-(1'-sulfonaphth-2'-ylazo)-7- (5'-amino-2'-sulfophenylazo)-8-aminonaphthalene-3,6-dinu-phonic acid, 1-hydroxy-2-(1'-sulfonaphth-2'-ylazo)-7-(5 '-amino-2'-sulfophenylazo)-8-aminonaphthalene-8,5-disulfonic acid, 1-hydroxy-2-(5'-amino-2'-sulfophenylazo)-7-(1' -sulfonaphtho-21~azo)-8-aminonaphthalene-8,6-disulfonic acid, 1~hydroxy-2-(5'-amino-2'sulfofenipazo)-7-(1'-sulfonaphtho-2p -ylazo)-8-aminonaphthalene-8,5-disulfonic acid, 1-hydroxy-2-(1'-sulfonaphtho-21-iazo)-7-(5'-amino-2'4'-disulfonate) phenylazo)-8-amitunaphthanone-8,6-disρ
Phonic acid, 1-hydroxy-2-(i'-sulfonaphth-2'-ylazo)-7-(5'-amino-2'4#-disulfophenylazo)-8-aminonaphthalene-8,5-disulfone acid, 1-hydroxy-2-(5'-amino-2'4'-disulfophenylazo)-7-(1'-sulfonaphtho-21
~azo)-8-aminonaphthalene-8,6-disμ
Fonic acid, 1-hydroxy-2-(5'-amino-2'4'-disulfophenylazo)-7-(1'-sulfonaphtho-21
~ylazo)-8-aminonaphthalene-3,5-disulfonic acid, 1-hydroxy-2-(1',7'-disulfonaphtho-2'-ylazo)-7-(5'-amino-2'-sp
Phopheniazo)-8-7minonaphthalene-8,6-disulfonic acid, 1-hydroxy-2-(5'-amino-2'-sulfopheniazo)-7-(1',7'-disulfonate) Phenylnaphthol 21-azone-8-aminonaphthalene-
8,6-disulfonic acid, (17) l-hydroxy-2-(5'-amino-2'-sulfopheniazo)-7-(6'-sulfonaphtho-21-ylazo)-8-aminonaphthalene- 8,6-disulfonic acid, l-hydroxy-2-(5'-amino-2'sphophenylazo)-7-(8'-nuhonaphtho21-ylazo)-8-aminonaphthalene-8,6 -disulfonic acid, 1-hydroxy-2-(5'-amino-2'spofenipazo)-7-(6'-sulfonaphtho-21-ylazo)-8-aminonaphthalene-8,5-disulfonic acid, 1-hydroxy-2-(1'-sulfonaphth-2'-ylazo)-7-(4'-amino-2'-suphophenylazo)-8-aminonaphthalene-8,6-disulfonic acid, 1-hydroxy- 2-(1'-sulfonaphth-2'-ylazo)-7-(4'-amino-2',5'-disulfophenylazo)-8-aminonaphthalene-8,6-dispphonic acid, (18 ) 1-hydroxy- 2-(1-sulfonaphtho2'-ylazo)-7-(4'-amino-255'-disulfophenylazo)-8-aminonaphthalene-3,5-disulfonic acid, 1-hydroxy- 2-(1'-sulfo-5'aminomethylnaphtho-2'-ylazo)-7-(21-sulfophenylazo)-8-aminonaphthalene-3,6-disulfonic acid, 1-hydrohesyl-( 2'-sulfophenylazo)-7-(1'-sulfo-5'-aminomethylnaphtho-
21~A/azo)-8-aminonaphthalene-3,6-
Disulfonic acid, I-hydroxy-2-(1,'-su~ho-5'aminomethylnaphtho-・2'-ylazo)・~7-(1'-sulfonaphtho-2'-ylazo)-8-7minonaphthalene-3 .6-disulfonic acid, 1-hydroxy-2-(
]'-sulfonaphtho-2'-ylazo) -7-(]
,, ]'-sulfo-5'aminomethylnaphtho-21~
ylazo)-8-aminonaphthalene-8,6-disulfonic acid, 1-hydroxy-2-(1',7'-disulfo5'-aminzmedelnaphtho2'-i/1/
azo)-7-(2'-sulfophenylazo)-8-aminonaphthalene-8,6-disulfonic acid, 1-hydroxy-2-(2'-sulfophene':'ruazo)-7-(1
',7'-disulfo-51-aminomethylnaphtho-2
'~ipazo)-8-aminonaphthalene-8,6-disulfonic acid, 1~hydroyac-2-(5'-aminomethyl4'-methy/L/21~sulfophenylazo)・
-7-(1'-sulfonaphtho-2'-ylazo)-8-
7minonaphthalene-8.6-disulfonic acid, 1-hydroxy-2-(1,'-sulfonaf)-21-ylazo)-7-(5'-aminomethyl-41-methy/L/
2 #-SulfofX2-azo)-8-aminonaphthalene-8,6-disulfonic acid, 1-hydroxy-2-(2'
-sulfophenyl"azo)-7-(5'-amino-2
'-sulfophenylazo)-8-aminonaphthalene-8
, 6-dispphonic acid, ■-Hydroxy~1~(5'-amino-2', lehophenylazo)-7-(2'-nuphophenylazo)-
8-Aminopooptalene'-8. G-disulfonic acid, 1-hydroxy-2 (21-sulfob X nylazo)
7 (5'-amino-2', 4'-disulfophenyl azo>-S, -aminonaphthalene-3,6-disulfonic acid, 1-bitorology 2-(1'-sulfonaphtho-2'-
ylazo)-'1-(1',7'-disulfo5'-aminomethylnaphtho-21-ylazo)-8-aminonaphthalene-3,6-disulfonic acid, 1-hydroxy-2-(
1'-sulfonaphtho-2'-ylazo)-7-(5'-
amino-4'-methyl-2'-sulfophenylazo)-
8-aminonaphthalene-8,6-disulfonic acid, 1-HydroA゛C 2-(5'-amino-2'Merhoff, Nylazo)-7-FJ Nylazo-8-aminonaphthalene-8,6-disulfonic acid , 1~Hydro A゛C 2
- (5'-amino-2'(21) 4'-disulfophenylazo)-7-pheny/l/azo 8-aminonaphthalene-81,6-disulfonic acid, and the like.
本発明化合物は、繊維反応性を有し、ヒドロキシ基含有
または力ρ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しドロキン基含有
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 doroquine group-containing materials, such as cellulose fiber materials or their regenerated products and polyvinyl alcohol.
セルロースミｍ材料は木綿、しかもその他の植物繊維、
たとえばリネン、麻、ジュート及びフミー繊維が好まし
い。再生セルロース繊維はたとえばビスコース壽ステー
ブル及びフィフメントビスコスである。Cellulose material is cotton, as well as other vegetable fibers,
For example, linen, hemp, jute and humi fibers are preferred. Regenerated cellulose fibers are, for example, viscose stable and fifmented 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（２２）
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, poly(22)amide-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、七μローヌ繊維上に吸尽染色する場合、炭酸ソ
ーダ、第三燐酸ソーダ、苛性ソーダ等の酸結合剤の存在
下、場合により中性塩、例えば芒硝又は食塩を加え、所
望によっては、溶解助剤、浸透剤又は均染剤を併用し、
比較的低い温度で行われる。染料の吸尽を促進する中性
塩は、本来の染色温度に達した後に初めて又はそれ以前
に、場合によっては分割して添加できる。For example, when exhaust dyeing is carried out on 7μ Rhône 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, dissolved. Using auxiliary agents, penetrants or leveling agents together,
It is carried out at relatively low temperatures. The neutral salts which accelerate the exhaustion of the dyestuff can be added only after the actual dyeing temperature has been reached, or even before then, optionally in portions.
バジング法に従って七μロ〜ス繊維を染色する場合、室
温又は高められた温度でパッドし乾燥後、スチーミング
又は乾熱によって固着できる。When dyeing 7μ loin fibers according to the bagging method, it can be padded at room temperature or elevated temperature, dried and then fixed by steaming or dry heat.
セルロースＩＪｌ！維に対して捺染を行う場合、−相で
、例えば重曹又はその他の酸縮合剤を含有する捺染ペー
ストで捺染し、次いで１ｏｏ〜１６０’Ｃでスチーミン
グすることによって、あるいは＝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７μカＩＪ ｉ４電解質含
有バジング液でオーバーパジングし、スチーミング又は
乾熱処理して実施できる。Cellulose IJl! When printing is carried out on fibers, printing is carried out in the -phase, e.g. with a printing paste containing baking soda or other acid condensing agent, followed by steaming at 100 to 160'C, or in the -phase, e.g. This can be carried out by printing with a neutral or weakly acidic printing paste, passing it through a hot electrolyte-containing alkaline bath, or by overpadding with a 7μ IJ i4 electrolyte-containing bagging solution and by steaming or dry heat treatment.
捺染ペーストには、例え１ばアルギン酸ソーダ又は澱粉
エーテルのような糊剤又は乳化剤が、所望によっては、
例えば尿素のような通常の捺染助剤かつ（又は）分散剤
と併用して用いられる。The printing paste may contain thickening agents or emulsifiers, such as sodium alginate or starch ether, if desired.
It is used in combination with conventional printing aids and/or dispersants, such as urea.
セルローヌ繊維−Ｈに本発明化合物を固定させるに適し
た酸結合剤は、例えばアルカリ土類又はアルカリ土類金
属と無揚又拡有機酸あるい（伏角熱状態でアＡ・カリ遊
離する化合物との水溶性橿基性塩でちる。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、
例えは苛性ソーダ、苛性カリ、重曹、炭酸ソーダ、蟻酸
ソーダ、次酸カリ、第一、第二又は第三燐酸ソーダ、ケ
イ酸ソーダ、トリクロロ酢酸ソーダ等が挙げられる。Acid binders suitable for fixing the compound of the present invention to Cellulone fiber-H include, for example, alkaline earths or alkaline earth metals and non-elevated or expanded organic acids (compounds that release acetate and potash in dipping heat conditions). Particularly preferred are 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. As such an acid binder,
Examples include caustic soda, caustic potash, sodium bicarbonate, sodium carbonate, sodium formate, potassium subacid, primary, secondary, or tertiary sodium phosphate, sodium silicate, sodium trichloroacetate, and the like.
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、場合によシアルカ
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 ’Ｃの温度で行えるが、均染性を達
成する丸めに通常）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はステアｖｉｖ
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 acidic or slightly acidic dye baths, and then by changing to a neutral, sometimes alkaline, pH value for fixation. It can be done by Dyeing is usually carried out at a temperature of 60-120'C, but to achieve leveling (usually for rounding) a leveling agent, such as a condensation product of cyanuric chloride and 8 times the molar amount of aminobenzenesulfonic acid or aminonaphthalenesulfonic acid. Or, for example, Stare viv
Addition products of amines and ethylene oxide can also be used.
本発明化合物は繊維材料に対する染色及び捺染におｈ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シ、良好な耐
光性と耐汗日光性、優れた耐湿潤性、たとえばｌ１ｌ）
ｌ５ｌ−層性、耐過酸化洗濯性、耐塩素性、耐汗性、耐
酸加水分解性及び耐アルカリ性、更に良好な耐摩擦性と
耐アイロン性を有する。Particularly suitable for dyeing cellulose fiber materials, with good light and sweat resistance, excellent moisture resistance, such as l1l)
It has l5l-layer properties, peroxide washing resistance, chlorine resistance, sweat resistance, acid hydrolysis resistance and alkali resistance, as well as good abrasion resistance and ironing resistance.
また優れたビμドアッグ性、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（２６）
を有する点、染色温度や染浴此の変動にょる影譬を受け
に〈〈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 bidagability, level dyeing and wash-off properties, as well as good solubility, exhaustion and fixation properties (26), and is resistant to the effects of fluctuations in dyeing temperature and dye bath. It is characterized by the fact that dyed products of stable quality can be obtained.
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、実施例によシ本発明の詳細な説明する。Hereinafter, the present invention will be explained in detail by way of 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 １
常法によ、り、２．４−ジアミノベンゼンスルホン酸４
．７０部と塩化シアヌ／Ｉ／４．６１部を縮合させ、次
に１〜アミノベンゼン−８−ベータースルフ１〜 トｘ
−ｔ−ｙｖｙ、ｉｖホン６、ｇ ５部と縮合し、これを
ジアゾ化後、１〜アミノ−８−ヒドロキシナフタンンー
３．６−ジスμホン酸７．７３部と強酸曲Ｆでカップリ
ングし、さらに２−ナフナルアミンー６−ベータースル
ファートエチルスルホン−１〜スルホン酸１０．２５部
のジアゾ化合物とカッグリン（２６〕
グさせた。反応溶液を塩化ナトリウムで塩析することに
より、遊Ｍ＆酸の形で−Ｆ式
％式％）
で示されるビスアゾ化合物を得た。Example 1 2,4-diaminobenzenesulfonic acid 4 was prepared by a conventional method.
．． 70 parts of cyanuric chloride/I/4.61 parts are condensed, and then 1~aminobenzene-8-betersulfur 1~tx
Condensation with 5 parts of -t-yvy, IV phone 6, g, diazotization, and coupling with 7.73 parts of 1-amino-8-hydroxynaphthane-3,6-disulfonic acid using strong acid program F. Then, a diazo compound of 2-nafnalamine-6-beta-sulfate ethyl sulfone-1 and 10.25 parts of sulfonic acid was added to Cagrin (26).The reaction solution was salted out with sodium chloride to separate the free M&acid. A bisazo compound represented by the form -Fformula%formula%) was obtained.
実施例 ２
実施例１において使用した２−ナフ千〜アミン−６−ペ
ータースルフアー トエチルスルホンー１〜スｗホンｔ
＆、２ 、４−ジアミノベンゼンスルホンｆｉ、ｌ−ア
ミノ−８−ヒドロキシナフタレン−８，６−ジスルホン
Ｍ、Ｉ−アミノベンゼン−８−ベータースルフアートエ
チルスルホンの代ワリに、順にＦ表、第２欄、第８＃、
第４個及び第５欄、の化合物を用いて実施例１と同様に
合成し、各々対応するどスアゾ化合物を得、染色して下
表第６欄に示す色調の染色物を得た。Example 2 2-naph-amine-6-petersulfone ethylsulfone-1 used in Example 1
&, 2, 4-diaminobenzenesulfone fi, l-amino-8-hydroxynaphthalene-8,6-disulfone M, I-aminobenzene-8-beta-sulfatoethylsulfone, Table F, Table Column 2, #8,
The compounds in the fourth and fifth columns were synthesized in the same manner as in Example 1 to obtain the corresponding dosuazo compounds, which were dyed to obtain dyed products having the tones shown in the sixth column of the table below.
（２９）
（８０）
（８１）
（８２）
（之ｊ５）
（８６）
実施例 ３
実施例１と同様に、但し１〜アミノ−８−ヒドロキシカ
フグレン−８，６−ジスルホン酸と２種のジアゾ化合物
のカップリング順序を逆転させて実施し、遊離酸の形で
下式
％式％）
で示されるビスアゾ化合物を得た。(29) (80) (81) (82) (之j5) (86) Example 3 Same as Example 1, except that 1-amino-8-hydroxycafuglene-8,6-disulfonic acid and two types of The coupling order of the diazo compound was reversed to obtain a bisazo compound of the following formula in the free acid form.
実施例 ４
実施例２の表中、各第１欄の厖において表わされた化合
物を用い、実施例８と同様の方法で対応するビスアゾ化
合物を合成した。Example 4 The corresponding bisazo compounds were synthesized in the same manner as in Example 8 using the compounds shown in the columns of each first column in the table of Example 2.
実施例 ５
実施例１〜４において、塩化シアノ〜の代わυにフッ化
シアヌルを用い、同様の方法で対応するビスアゾ化合物
を合成した。Example 5 In Examples 1 to 4, the corresponding bisazo compounds were synthesized in the same manner using cyanuric fluoride instead of cyano chloride.
（４１）
実施例 ６
実施例１〜５に記載の各々のビスアゾ化合物０．１．０
．８及び０．６部を各々水２００部に溶解し、芒硝１０
部と木綿１０部を加え、６０℃に昇温し炭酸ソーダ４部
を加えて１時間染色し九。水洗、ソーピング、水洗そし
て乾燥を行い、諸竪牢度に優れ、良好なビルドアップ性
を有するネービー色の染色物が得られた。(41) Example 6 Each bisazo compound described in Examples 1 to 5 0.1.0
．． Dissolve 8 parts and 0.6 parts in 200 parts of water, and add 10 parts of Glauber's salt.
10 parts of cotton and 10 parts of cotton were heated to 60°C, 4 parts of soda carbonate was added, and dyed for 1 hour.9. After washing with water, soaping, rinsing with water and drying, a navy-colored dyed product with excellent firmness and good build-up properties was obtained.
実施例 ７
実施例１〜５に記載の各々のビスアゾ化合物のそれぞれ
を用いて、以下の組成をもつ色糊を作−また。Example 7 Using each of the bisazo compounds described in Examples 1 to 5, a colored paste having the following composition was prepared.
ビスアゾ化合物 ５部民
素 ５部アルギン
酸ソーダ（５％）元糊 ５０部熱 湯
２５部重
曹 ２部バ ラ
ン ス １
８部この色糊をシルケット加工線ブロード上に印捺し、
中間乾燥後、１００℃で５分間スチーミング（４２）
を行い、
湯洗い、
ソーピング、
湯洗いそし７て乾燥
し、
諸堅牢度に優れたネービー色の捺染物が得られた。Bisazo compound 5th grade
Base: 5 parts Sodium alginate (5%) Paste: 50 parts Hot water: 25 parts Weight
Cao 2nd part rose
nce 1
Part 8: Print this color paste on broad mercerized wire,
After intermediate drying, it was steamed at 100°C for 5 minutes (42), washed with hot water, soaped, washed with hot water, dried, and a navy-colored print with excellent fastness was obtained.
（以下余白 ） （４８）完(Margin below ) (48) Completed
Claims (6)
２は、互いに独立に−ＳＯ＿２ＣＨ＝ＣＨ＿２、または
−ＳＯ＿２ＣＨ＿２ＣＨ＿２Ｚ′を表し、Ｚ′はアルカ
リの作用で脱離する基を表す。Ａは、置換されていても
よいフェニレンまたはナフチレン基を表す。Ｂは、下式
▲数式、化学式、表等があります▼０または１または▲
数式、化学式、表等があります▼０または１ （式中、＊印は、アゾ基に接続する結合を、Ｒ＿８は水
素、メチル基またはスルホ基を表す。）で示される基を
表す。Ｄは、アルキル、アルコキシ、カルボキシおよび
スルホの群から選ばれる、１又は２個の置換基により置
換されていてもよいフェニレン基、またはスルホによっ
て置換されていてもよいナフチレン基を表す。Ｒ＿１お
よびＲ＿２は、互いに独立に水素又は置換されていても
よいアルキル基を表す。Ｘ＿１及びＸ＿２は、一方がＮ
Ｈ＿２基で、他方がＯＨ基を表す。〕で示されるビスア
ゾ化合物。(1) In the form of a free acid, there are the following general formulas ▲ mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, X is chlorine or fluorine, Z_1 and Z_
2 independently represent -SO_2CH=CH_2 or -SO_2CH_2CH_2Z', and Z' represents a group that is eliminated by the action of an alkali. A represents an optionally substituted phenylene or naphthylene group. B is the following formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ 0 or 1 or ▲
There are mathematical formulas, chemical formulas, tables, etc.▼0 or 1 (In the formula, the * mark represents a bond connected to an azo group, and R_8 represents hydrogen, a methyl group, or a sulfo group.) Represents a group. D represents a phenylene group optionally substituted with one or two substituents selected from the group of alkyl, alkoxy, carboxy and sulfo, or a naphthylene group optionally substituted with sulfo. R_1 and R_2 each independently represent hydrogen or an optionally substituted alkyl group. One of X_1 and X_2 is N
One is an H_2 group, and the other one is an OH group. ] A bisazo compound represented by
Ｒ＿２は、請求項１に記載の意味を有する。〕で示され
る請求項１に記載の化合物。(2) In the form of free acid, there is the following general formula ▲ mathematical formula, chemical formula, table, etc. ▼ [In the formula, Z_1, Z_2, A, B, D, have ] The compound according to claim 1.
レンまたはナフチレン基である請求項１または２に記載
の化合物。(3) The compound according to claim 1 or 2, wherein D is a phenylene or naphthylene group having a sulfo group at the ortho position of the azo group.
たはエチルである請求項１〜８の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_1 and R_2 are independently hydrogen, methyl or ethyl.
Ｈ＝ＣＨ＿２または−ＳＯ＿２ＣＨ＿２ＣＨ＿２ＯＳＯ
＿３Ｈである請求項１〜４のいずれかに記載の化合物。(5) Z_1 and Z_2 independently of each other -SO_2C
H=CH_2 or -SO_2CH_2CH_2OSO
The compound according to any one of claims 1 to 4, which is _3H.
特徴とする繊維材料を染色または捺染する方法。(6) A method for dyeing or printing a fiber material, which comprises using the bisazo compound according to claim 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2063714A JP2943219B2 (en) | 1990-03-13 | 1990-03-13 | Bisazo compound and method for dyeing or printing fiber material using the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2063714A JP2943219B2 (en) | 1990-03-13 | 1990-03-13 | Bisazo compound and method for dyeing or printing fiber material using the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH03263469A true JPH03263469A (en) | 1991-11-22 |
| JP2943219B2 JP2943219B2 (en) | 1999-08-30 |
Family
ID=13237331
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2063714A Expired - Lifetime JP2943219B2 (en) | 1990-03-13 | 1990-03-13 | Bisazo compound and method for dyeing or printing fiber material using the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2943219B2 (en) |
-
1990
- 1990-03-13 JP JP2063714A patent/JP2943219B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JP2943219B2 (en) | 1999-08-30 |
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