JPS62288659A - Production of novel hexakisazo dye - Google Patents
Production of novel hexakisazo dyeInfo
- Publication number
- JPS62288659A JPS62288659A JP13251986A JP13251986A JPS62288659A JP S62288659 A JPS62288659 A JP S62288659A JP 13251986 A JP13251986 A JP 13251986A JP 13251986 A JP13251986 A JP 13251986A JP S62288659 A JPS62288659 A JP S62288659A
- Authority
- JP
- Japan
- Prior art keywords
- dye
- hexakisazo
- formula
- general formula
- formulas
- 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.)
- Pending
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- -1 alicyclic amine Chemical class 0.000 claims abstract description 12
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims abstract description 4
- 150000004982 aromatic amines Chemical class 0.000 claims abstract description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims abstract 6
- 125000000542 sulfonic acid group Chemical group 0.000 claims abstract 3
- 125000002723 alicyclic group Chemical group 0.000 claims abstract 2
- 125000001931 aliphatic group Chemical group 0.000 claims abstract 2
- 125000003118 aryl group Chemical group 0.000 claims abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 2
- 125000001453 quaternary ammonium group Chemical group 0.000 claims abstract 2
- 239000000126 substance Substances 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 235000014113 dietary fatty acids Nutrition 0.000 claims 1
- 229930195729 fatty acid Natural products 0.000 claims 1
- 239000000194 fatty acid Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 28
- 239000000463 material Substances 0.000 abstract description 4
- 239000004952 Polyamide Substances 0.000 abstract description 3
- 239000001913 cellulose Substances 0.000 abstract description 3
- 229920002678 cellulose Polymers 0.000 abstract description 3
- 239000010985 leather Substances 0.000 abstract description 3
- 229920002647 polyamide Polymers 0.000 abstract description 3
- 238000004040 coloring Methods 0.000 abstract description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- 239000000975 dye Substances 0.000 description 54
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 239000002253 acid Substances 0.000 description 14
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 239000000976 ink Substances 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 7
- 230000008878 coupling Effects 0.000 description 5
- 238000010168 coupling process Methods 0.000 description 5
- 238000005859 coupling reaction Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000005185 salting out Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000987 azo dye Substances 0.000 description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 150000003839 salts Chemical group 0.000 description 3
- 235000002639 sodium chloride Nutrition 0.000 description 3
- OWRCNXZUPFZXOS-UHFFFAOYSA-N 1,3-diphenylguanidine Chemical compound C=1C=CC=CC=1NC(=N)NC1=CC=CC=C1 OWRCNXZUPFZXOS-UHFFFAOYSA-N 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 description 2
- 235000013162 Cocos nucifera Nutrition 0.000 description 2
- 244000060011 Cocos nucifera Species 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 238000003916 acid precipitation Methods 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 239000013076 target substance Substances 0.000 description 2
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 2
- 150000004992 toluidines Chemical class 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- QGLWBTPVKHMVHM-KTKRTIGZSA-N (z)-octadec-9-en-1-amine Chemical compound CCCCCCCC\C=C/CCCCCCCCN QGLWBTPVKHMVHM-KTKRTIGZSA-N 0.000 description 1
- OPNUROKCUBTKLF-UHFFFAOYSA-N 1,2-bis(2-methylphenyl)guanidine Chemical compound CC1=CC=CC=C1N\C(N)=N\C1=CC=CC=C1C OPNUROKCUBTKLF-UHFFFAOYSA-N 0.000 description 1
- HKGKYUVCADNOOC-UHFFFAOYSA-N 1-aminotetradecan-2-ol Chemical compound CCCCCCCCCCCCC(O)CN HKGKYUVCADNOOC-UHFFFAOYSA-N 0.000 description 1
- CDULGHZNHURECF-UHFFFAOYSA-N 2,3-dimethylaniline 2,4-dimethylaniline 2,5-dimethylaniline 2,6-dimethylaniline 3,4-dimethylaniline 3,5-dimethylaniline Chemical group CC1=CC=C(N)C(C)=C1.CC1=CC=C(C)C(N)=C1.CC1=CC(C)=CC(N)=C1.CC1=CC=C(N)C=C1C.CC1=CC=CC(N)=C1C.CC1=CC=CC(C)=C1N CDULGHZNHURECF-UHFFFAOYSA-N 0.000 description 1
- QIJIUJYANDSEKG-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-amine Chemical compound CC(C)(C)CC(C)(C)N QIJIUJYANDSEKG-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- MJNYPLCGWXFYPD-UHFFFAOYSA-N 2-amino-5-sulfobenzoic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1C(O)=O MJNYPLCGWXFYPD-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
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- LTHNHFOGQMKPOV-UHFFFAOYSA-N 2-ethylhexan-1-amine Chemical compound CCCCC(CC)CN LTHNHFOGQMKPOV-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- CYWGSFFHHMQKET-UHFFFAOYSA-N 2-methylsulfanylethanamine Chemical compound CSCCN CYWGSFFHHMQKET-UHFFFAOYSA-N 0.000 description 1
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
- DVFGEIYOLIFSRX-UHFFFAOYSA-N 3-(2-ethylhexoxy)propan-1-amine Chemical compound CCCCC(CC)COCCCN DVFGEIYOLIFSRX-UHFFFAOYSA-N 0.000 description 1
- ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-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
- USWINTIHFQKJTR-UHFFFAOYSA-N 3-hydroxynaphthalene-2,7-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C=C(S(O)(=O)=O)C(O)=CC2=C1 USWINTIHFQKJTR-UHFFFAOYSA-N 0.000 description 1
- FAXDZWQIWUSWJH-UHFFFAOYSA-N 3-methoxypropan-1-amine Chemical compound COCCCN FAXDZWQIWUSWJH-UHFFFAOYSA-N 0.000 description 1
- LRDIEHDJWYRVPT-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-1-sulfonic acid Chemical compound C1=CC(O)=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 LRDIEHDJWYRVPT-UHFFFAOYSA-N 0.000 description 1
- XPAQFJJCWGSXGJ-UHFFFAOYSA-N 4-amino-n-(4-aminophenyl)benzamide Chemical compound C1=CC(N)=CC=C1NC(=O)C1=CC=C(N)C=C1 XPAQFJJCWGSXGJ-UHFFFAOYSA-N 0.000 description 1
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-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
- FEPBITJSIHRMRT-UHFFFAOYSA-N 4-hydroxybenzenesulfonic acid Chemical compound OC1=CC=C(S(O)(=O)=O)C=C1 FEPBITJSIHRMRT-UHFFFAOYSA-N 0.000 description 1
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 1
- ZBIBQNVRTVLOHQ-UHFFFAOYSA-N 5-aminonaphthalen-1-ol Chemical compound C1=CC=C2C(N)=CC=CC2=C1O ZBIBQNVRTVLOHQ-UHFFFAOYSA-N 0.000 description 1
- YLKCHWCYYNKADS-UHFFFAOYSA-N 5-hydroxynaphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(O)=CC=CC2=C1S(O)(=O)=O YLKCHWCYYNKADS-UHFFFAOYSA-N 0.000 description 1
- YCPXWRQRBFJBPZ-UHFFFAOYSA-N 5-sulfosalicylic acid Chemical compound OC(=O)C1=CC(S(O)(=O)=O)=CC=C1O YCPXWRQRBFJBPZ-UHFFFAOYSA-N 0.000 description 1
- HBZVNWNSRNTWPS-UHFFFAOYSA-N 6-amino-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C(O)C2=CC(N)=CC=C21 HBZVNWNSRNTWPS-UHFFFAOYSA-N 0.000 description 1
- GGZZISOUXJHYOY-UHFFFAOYSA-N 8-amino-4-hydroxynaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C(N)=CC=CC2=C1O GGZZISOUXJHYOY-UHFFFAOYSA-N 0.000 description 1
- CYJJLCDCWVZEDZ-UHFFFAOYSA-N 8-aminonaphthalene-1-sulfonic acid Chemical compound C1=CC(S(O)(=O)=O)=C2C(N)=CC=CC2=C1 CYJJLCDCWVZEDZ-UHFFFAOYSA-N 0.000 description 1
- QEZZCWMQXHXAFG-UHFFFAOYSA-N 8-aminonaphthalene-2-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C(N)=CC=CC2=C1 QEZZCWMQXHXAFG-UHFFFAOYSA-N 0.000 description 1
- ZPLBZGGKAUXTRT-UHFFFAOYSA-N 8-hydroxynaphthalene-1-sulfonic acid Chemical compound C1=CC(S(O)(=O)=O)=C2C(O)=CC=CC2=C1 ZPLBZGGKAUXTRT-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241000282320 Panthera leo Species 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- CYDRXTMLKJDRQH-UHFFFAOYSA-N benzododecinium Chemical compound CCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 CYDRXTMLKJDRQH-UHFFFAOYSA-N 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 1
- 229950011260 betanaphthol Drugs 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- DDXLVDQZPFLQMZ-UHFFFAOYSA-M dodecyl(trimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)C DDXLVDQZPFLQMZ-UHFFFAOYSA-M 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 1
- KDSNLYIMUZNERS-UHFFFAOYSA-N isobutyl amine Natural products CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- KVKFRMCSXWQSNT-UHFFFAOYSA-N n,n'-dimethylethane-1,2-diamine Chemical compound CNCCNC KVKFRMCSXWQSNT-UHFFFAOYSA-N 0.000 description 1
- VSHTWPWTCXQLQN-UHFFFAOYSA-N n-butylaniline Chemical compound CCCCNC1=CC=CC=C1 VSHTWPWTCXQLQN-UHFFFAOYSA-N 0.000 description 1
- NRZRRZAVMCAKEP-UHFFFAOYSA-N naphthionic acid Chemical compound C1=CC=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 NRZRRZAVMCAKEP-UHFFFAOYSA-N 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- WXWCDTXEKCVRRO-UHFFFAOYSA-N para-Cresidine Chemical compound COC1=CC=C(C)C=C1N WXWCDTXEKCVRRO-UHFFFAOYSA-N 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- IAAKNVCARVEIFS-UHFFFAOYSA-M sodium;4-hydroxynaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(O)=CC=C(S([O-])(=O)=O)C2=C1 IAAKNVCARVEIFS-UHFFFAOYSA-M 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- QHTJNIWEAQKWRP-UHFFFAOYSA-M triethyl(octadecyl)azanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCCCC[N+](CC)(CC)CC QHTJNIWEAQKWRP-UHFFFAOYSA-M 0.000 description 1
Landscapes
- Inks, Pencil-Leads, Or Crayons (AREA)
Abstract
Description
【発明の詳細な説明】
［産業上の利用分野］
本発明は、筆記具用・ジェット印刷用・記録計用インキ
、セルロース、天然または合成ポリアミド材料、皮革等
を着色するのに好適な新規へキサキスアゾ染料の製造法
に関する。Detailed Description of the Invention [Field of Industrial Application] The present invention provides novel hexakisazo inks suitable for coloring writing instruments, jet printing, recorder inks, cellulose, natural or synthetic polyamide materials, leather, etc. Concerning a method of manufacturing dyes.
［従来の技術］
従来、アゾ染料及び該アゾ染料を含有する水性インキ組
成物については、種々のものが開示されているが、これ
らは、極めて広汎な用途とそれに伴う多大の産業利用性
を有し、そしてその故に、より効果の大なるアゾ染料の
開発は、斯界の懸案であった。[Prior Art] Conventionally, various azo dyes and aqueous ink compositions containing the azo dyes have been disclosed, but these have extremely wide range of uses and correspondingly great industrial applicability. Therefore, the development of more effective azo dyes has been a concern in the industry.
［発明が解決しようとする問題点］
本発明は、如上の斯界の懸案に即応して、黒色性の極め
て良好な色調を有し、耐水性°耐光性・溶解安定性茅に
おいて卓越して、従来にその比をみない広汎な産業利用
性を有する新規なヘキサキスアゾ染料を提供せんとする
ものである。[Problems to be Solved by the Invention] The present invention, in immediate response to the above-mentioned concerns in the field, has an extremely good black color tone, excellent water resistance, light resistance, and dissolution stability. The object of the present invention is to provide a new hexakisazo dye that has a wide range of industrial applicability that has never been seen before.
［問題点を解決するための手段］
本発明方法の構成は、次の一般式
％式％（
で表されるヘキサキスアゾ染料に、脂肪酸アミン類、脂
環族アミン類、芳香族アミン類または第４級アンモニウ
ム塩類を作用させることにより、一般式
で表される、新規なヘキサキスアゾ染料を製造する方法
に係るものである。[Means for Solving the Problems] The method of the present invention has a structure in which a hexakisazo dye represented by the following general formula % ( The present invention relates to a method for producing a novel hexakisazo dye represented by the general formula by reacting with a class ammonium salt.
［実施例］
本発明に用いられる一般式（１）で表されるヘキサキス
アゾ染料は、次の諸工程により得られる。 第１工程ニ
一般式
で表される化合物を常法によりテトラゾ化し、次いで、
一般式
〔式中１ｍは、０．１または２を示す、〕で表される化
合物とカップリングを行ない、ジスアゾ染料を得る。[Example] The hexakisazo dye represented by the general formula (1) used in the present invention is obtained by the following steps. In the first step, the compound represented by the general formula is tetrazotized by a conventional method, and then,
Coupling is performed with a compound represented by the general formula [wherein 1m represents 0.1 or 2] to obtain a disazo dye.
第２工程ニ一般式
で表される化合物、あるいは、一般式
で表される化合物をジアゾ化し、次いで、第１工程で得
たジスアゾ染料とカップリングして、テトラキスアゾ染
料を得る。In the second step, the compound represented by the general formula or the compound represented by the general formula is diazotized and then coupled with the disazo dye obtained in the first step to obtain a tetrakisazo dye.
第３工程：得られたテトラキスアゾ染料を再度ジアゾ化
し、得られたテトラキスアゾ染料を、一般式
で表される化合物、あるいは、一般式
で表される化合物の単独または混合物とカップリングす
ることにより、目的とするヘキサキスアゾ染料が得られ
る。Third step: By diazotizing the obtained tetrakisazo dye again and coupling the obtained tetrakisazo dye with a compound represented by the general formula, or a single compound or a mixture of compounds represented by the general formula. , the desired hexakisazo dye is obtained.
上記工程に代えて、一般式（５）で表される化合物、ま
たは、一般式（６）で表される化合物をジアゾ化し、次
いで、一般式（０で表される化合物にカップリングする
ことにより七ノアゾ染料を得、該七ノアゾ染料に、一般
式（３）で表される化合物をテトラゾ化し、カップリン
グしてテトラキスアゾ染料を得る。得られたテトラキス
アゾ染料を再度テトラゾ化し、得られたテトラキスアゾ
染料を一般式（７）で表される化合物または一般式（８
）で表される化合物の単独または混合物とカップリング
を行ない、目的とするヘキサキスアゾ染料を得ることも
出来る。Instead of the above step, by diazotizing the compound represented by the general formula (5) or the compound represented by the general formula (6) and then coupling it to the compound represented by the general formula (0), A seven-noazo dye is obtained, and the seven-noazo dye is tetrazotized with a compound represented by the general formula (3) and coupled to obtain a tetrakisazo dye.The obtained tetrakisazo dye is again tetrazotized to obtain a A tetrakisazo dye is a compound represented by the general formula (7) or a compound represented by the general formula (8).
) The desired hexakisazo dye can also be obtained by coupling with compounds represented by (1) alone or in combination.
更にまた、第１工程で得られたジスアゾ染料を再度テト
ラゾ化し１次いで、一般式（７）で表される化合物また
は、一般式（８）で表される化合物の単独または混合物
とカップリングを行ないテトラキスアゾ染料を得る。こ
れに一般式（５）で表される化合物、または一般式（６
）で表される化合物をジアゾ化し、カップリングを行な
うことによっても、目的とするヘキサキスアゾ染料を得
ることが出来る。Furthermore, the disazo dye obtained in the first step is again tetrazotized and then coupled with a compound represented by general formula (7) or a compound represented by general formula (8) alone or in a mixture. Obtain a tetrakisazo dye. To this, a compound represented by general formula (5) or general formula (6
The desired hexakisazo dye can also be obtained by diazotizing the compound represented by ) and performing coupling.
前記の、一般式（１）で表される化合物を得る工程にお
いて、均質な出発原料化合物を使用するかわりに、混合
物１例えば一般式（５）で表される種々のアミンまたは
種々のアニリン誘導体を使用することも可能であり、そ
の場合には個々の染料と同様の性質を有する染料混合物
が得られる。また、目的に応じて。In the step of obtaining the compound represented by the general formula (1), instead of using a homogeneous starting material compound, the mixture 1, for example, various amines represented by the general formula (5) or various aniline derivatives, is used. It is also possible to use dye mixtures which have similar properties to the individual dyes. Also, depending on the purpose.
酸析φ塩析により精製される。該染料は、所望のアルカ
リでアルカリ塩とすることにより、溶解性のよい水溶性
染料が得られる。この場合におけるアルカリ源には、水
酸化ナトリウム、水酸化カリウム、水酸化リチウム、ア
ンモニア水等が用いられる。Purified by acid precipitation φ salting out. By converting the dye into an alkali salt with a desired alkali, a water-soluble dye with good solubility can be obtained. In this case, the alkali source used is sodium hydroxide, potassium hydroxide, lithium hydroxide, aqueous ammonia, or the like.
一般式（３）で表される化合物を例示すると、４．４’
−ジアミノスチルベン−２，２′−ジスルホン酸、４．
４′−ジアミノジフェニルエーテル、４．４’−ジアミ
ノジフェニルスルホン、３．３′−ジメチルベンジジン
、３．３’−ジメトキシベンジジン、３゜３′−ジクロ
ロベンジジン、２．２’−ベンジジンジスルホン酸、４
．４′−ジアミノジフェニルメタン、４．４′−ジアミ
ノジトリルメタン、４．４′−ジアミノトリフェニルメ
タン、４．４′−ジアミノ−３，３′−ジメトキシ−２
″−スルホトリフェニルメタン、４．４’−ジアミノベ
ンズアニリド等が挙げられる。Examples of compounds represented by general formula (3) include 4.4'
-diaminostilbene-2,2'-disulfonic acid, 4.
4'-diaminodiphenyl ether, 4.4'-diaminodiphenylsulfone, 3.3'-dimethylbenzidine, 3.3'-dimethoxybenzidine, 3°3'-dichlorobenzidine, 2.2'-benzidine disulfonic acid, 4
．． 4'-diaminodiphenylmethane, 4.4'-diaminoditolylmethane, 4.4'-diaminotriphenylmethane, 4.4'-diamino-3,3'-dimethoxy-2
″-sulfotriphenylmethane, 4,4′-diaminobenzanilide, and the like.
一般式（４）で表される化合物を例示すると、１−７ミ
ノー８−ナフトール−４−スルホン酸、２−アミノ−５
−ナフトール−７−スルホン酸、ｌ−アミノ−８−ナフ
トール−３，６−ジスルホン酸、ｌ−アミノ−８−ナフ
トール−４，６−ジスルホン酸等が挙げられる。Examples of compounds represented by general formula (4) include 1-7minor-8-naphthol-4-sulfonic acid, 2-amino-5
-naphthol-7-sulfonic acid, l-amino-8-naphthol-3,6-disulfonic acid, l-amino-8-naphthol-4,6-disulfonic acid, and the like.
一般式（５）で表される化合物を例示すると、ｌ−７ミ
ノナフタレン、１−アミノ−４−ナフタレンスルホン酸
、ｌ−アミノ−５−ナフタレンスルホン酸、ｌ−アミノ
−６−ナフタレンスルホン酸、ｌ−アミノ−７−ナフタ
レンスルホン酸、ｌ−アミノ−８−ナフタレンスルホン
酸、２−アミノ−１−ナフタレンスルホン酸、５−アミ
ノ−１−ナフトール。Examples of compounds represented by general formula (5) include l-7minonaphthalene, 1-amino-4-naphthalenesulfonic acid, l-amino-5-naphthalenesulfonic acid, l-amino-6-naphthalenesulfonic acid, 1-Amino-7-naphthalenesulfonic acid, 1-amino-8-naphthalenesulfonic acid, 2-amino-1-naphthalenesulfonic acid, 5-amino-1-naphthol.
ｌ−アミノ−５−ナフトール−７−スルホン酸、２−ア
ミノ−８−ナフトール−６−スルホ刈１ ｌ−アミノ−
８−ナフトール−２゜４−ジスルホン酸、ｌ−アミノ−
８−ナフトール−３，６−ジスルホンｍ、ｌ−アミノー
８−ナフトール−４，６−ジスルホン酸等が挙げられる
。1-amino-5-naphthol-7-sulfonic acid, 2-amino-8-naphthol-6-sulfonic acid 1 l-amino-
8-naphthol-2゜4-disulfonic acid, l-amino-
Examples include 8-naphthol-3,6-disulfone m and l-amino-8-naphthol-4,6-disulfonic acid.
一般式（６）で表される化合物を例示すると、アニリン
、トルイジン、キシリジン、ｐ−クロルアニリン、ｍ−
７ミノフエノール、アニシジン、ｐ−フェネチジン、ｐ
−クレシジン、アントラニル酸、５−スルホアントラニ
ル酸、ｐ−７ミノ安息香酸、メタニル酸、スｋ ７アニ
ル酸、ｐ−７ミノサリチル酸、ｐ −ニトロアニリン等
が挙げられる。Examples of compounds represented by general formula (6) include aniline, toluidine, xylidine, p-chloroaniline, m-
7 minophenol, anisidine, p-phenetidine, p
Examples include cresidine, anthranilic acid, 5-sulfoanthranilic acid, p-7 minobenzoic acid, metanilic acid, sk7anilic acid, p-7 minosalicylic acid, p-nitroaniline, and the like.
一般式（７）で表される化合物を例示すると、１−ナフ
トール、２〜ナフトール、ｌ−ナフトール−４−スルホ
ン酸、ｌ−ナフトール−５−スルホン酸、１−ナフトー
ル−８−スルホン酸、２−ナフトール−６−スルホン酸
、ｌ−ナフトール−３，６−ジスルホン酸、２−ナフト
ール−３，６−ジスルホン酸、８−クロロ−１−ナフト
ール−３，６−ジスルホン酸、２−ナフトール−３−カ
ルボン酸、ｌ−アミノ−６−ナフタレンスルホン酸、２
−アミツーｌ−ナフタレンスルホン酸、５−７ミノーｌ
−ナフトール、１−アミノ−８−ナフトール−４−スル
ホン酸、２−アミノ−５−ナフトール−７−スルホン酸
、２−アミノ−８−ナフトール−６−スルホン
アミノ−８−ナフトール−２，４−ジスルホン酸，ｌ−
アミノ−８−ナフトール−３，６−ジスルホン酸，１−
アミノ−８−ナフトール−４．６−ジスルホン酸等が挙
げられる。Examples of compounds represented by general formula (7) include 1-naphthol, 2-naphthol, 1-naphthol-4-sulfonic acid, 1-naphthol-5-sulfonic acid, 1-naphthol-8-sulfonic acid, 2-naphthol-4-sulfonic acid, -Naphthol-6-sulfonic acid, l-naphthol-3,6-disulfonic acid, 2-naphthol-3,6-disulfonic acid, 8-chloro-1-naphthol-3,6-disulfonic acid, 2-naphthol-3 -carboxylic acid, l-amino-6-naphthalenesulfonic acid, 2
-amito-l-naphthalenesulfonic acid, 5-7 minol
-Naphthol, 1-amino-8-naphthol-4-sulfonic acid, 2-amino-5-naphthol-7-sulfonic acid, 2-amino-8-naphthol-6-sulfonamino-8-naphthol-2,4- Disulfonic acid, l-
Amino-8-naphthol-3,6-disulfonic acid, 1-
Examples include amino-8-naphthol-4,6-disulfonic acid.
一般式（８）で表される化合物を例示すると、フェノー
ル、クロルフェノール、クレゾール、レゾルシノール、
フェノール−４−スルホン酸，ｍ−７ミノフエノール、
４−ｔ−ブチルフェノール、カテコール、フロログリシ
ン、４−ヒドロ午シアニソール，２−ｔ−ブチル−４−
ヒドロキシアニソール、サリチル酸、５−スルホサリチ
ル酸等が挙げられる。Examples of compounds represented by general formula (8) include phenol, chlorophenol, cresol, resorcinol,
Phenol-4-sulfonic acid, m-7 minophenol,
4-t-butylphenol, catechol, phloroglycin, 4-hydrocyanisole, 2-t-butyl-4-
Examples include hydroxyanisole, salicylic acid, 5-sulfosalicylic acid, and the like.
本発明方法においては、前述の諸工程により得られた一
般式（１）で示されるヘキサキスアゾ染料に，脂肪族ア
ミン類，脂環族アミン類，芳香族アミン類または第４級
アンモニウム塩類を作用させて目的物質たる一般式（２
）で表される新規なヘキサキスアゾ染料を得るのである
が、本発明において使用される各種アミンの具体的な例
としては、ｎ−ブチルアミン、ｉ−ブチルアミン、ｔ−
ブチルアミン、ｎ−オクチルアミン、ｔ−オクチルアミ
ン、ｎ−ドデシルアミン、ｔ−オクタデカアミン、メト
キシプロピルアミン、オクトキシプロピルアミン、ジメ
チルエチレンジアミン。In the method of the present invention, aliphatic amines, alicyclic amines, aromatic amines or quaternary ammonium salts are reacted on the hexakisazo dye represented by the general formula (1) obtained through the above-mentioned steps. The target substance is the general formula (2
), and specific examples of various amines used in the present invention include n-butylamine, i-butylamine, t-butylamine,
Butylamine, n-octylamine, t-octylamine, n-dodecylamine, t-octadecamine, methoxypropylamine, octoxypropylamine, dimethylethylenediamine.
オクチルプロピレンジアミン、ココナツトプロピレンジ
アミン、β−メチルチオエチルアミン、Ｎ，Ｎ−ビス−
（β−メチルチオエチル）−プロピレンジアミン、オレ
イルアミン、ココナツト７ミン、ジエチルアミン、ジ−
ｎ−ブチルアミン、トリメチルアミン、トリブチルアミ
ン、モノエタノールアミン、ジェタノールアミン、ドデ
シルエタノールアミンなどの脂肪族アミン類，シクロヘ
キシルアミン、ジシクロヘキシルアミン、モルホリンな
どの脂環族アミン類、アニリン、トルイジン、４−ｎ−
ブチルアニリン、ジフェニルグアニジン、ジトリルグア
ニジンなどの芳香族アミン類、トリエチルベンジルアン
モニウムクロライド、ドデシルジメチルベンジルアンモ
ニラムクミライド、ドデシルトリメチルアンモニウムク
ロライド、ドデシルトリエタノールアンモニウムクロラ
イド、ステアリルトリエチルアンモニウムブロマイド、
テトラブチルアンモニウムクロライドなどの４級アンモ
ニウム塩類が挙げられる。Octylpropylene diamine, coconut propylene diamine, β-methylthioethylamine, N,N-bis-
(β-Methylthioethyl)-propylenediamine, oleylamine, coconut 7mine, diethylamine, di-
Aliphatic amines such as n-butylamine, trimethylamine, tributylamine, monoethanolamine, jetanolamine, dodecylethanolamine, alicyclic amines such as cyclohexylamine, dicyclohexylamine, morpholine, aniline, toluidine, 4-n-
Aromatic amines such as butylaniline, diphenylguanidine, ditolylguanidine, triethylbenzylammonium chloride, dodecyldimethylbenzylammonium cumylide, dodecyltrimethylammonium chloride, dodecyltriethanolammonium chloride, stearyltriethylammonium bromide,
Examples include quaternary ammonium salts such as tetrabutylammonium chloride.
各種アミンは，その水溶性塩の形，例えば、酢酸．塩酸
または硫酸塩の形で有用に用いることができる，反応温
度は，−・般に１０乃至９５℃、好ましくは２０乃至７
０℃であり、いずれの場合も，もし可能であれば，水に
難溶の染料の塩が容易に中継できる結晶の形で沈殿する
ように選ばれる．必要ならば、塩析により染料塩を沈殿
せしめる。Various amines are available in their water-soluble salt forms, such as acetic acid. It can be usefully used in the form of hydrochloric acid or sulfate.The reaction temperature is generally between 10 and 95°C, preferably between 20 and 7°C.
0° C. and in each case chosen so that, if possible, the salts of dyes that are sparingly soluble in water precipitate in the form of easily relayable crystals. If necessary, the dye salts are precipitated by salting out.
さらに、Ｖｉ離耐酸型染料これは合成した染料を酸析に
より沈殿して得られる。）と、所定琶の各種アミンとの
混合物をニーダあるいは三本ロール上で、ただ単に常温
または加温下で練ることにより容易に一般式（２）で表
される目的物質を得ることができる。Furthermore, a Vi release acid-resistant dye is obtained by precipitating the synthesized dye by acid precipitation. ) and various amines of a predetermined amount are simply kneaded on a kneader or three rolls at room temperature or under heating, the target substance represented by the general formula (2) can be easily obtained.
以下に具体的実施例を示す。Specific examples are shown below.
実施例 １
次式
で表される染料１７１ｇを４ｆＬの水に加え６０〜７０
℃で溶解する０次に、２−エチルへキシルオキシプロピ
ルアミン７４．８ｇを３６％塩酸４４ｇと水で全容１Ｍ
の溶液をつくり、先の液に加え、２時間攪拌する０次い
で塩化カリを加え放冷し塩析を行う、沈殿をろ取し少量
の水で水洗した。５０℃で乾燥し、次式で表される黒色
粉末の造塩体染料２１６ｇ得た。Example 1 Add 171g of dye represented by the following formula to 4fL of water and
Next, 74.8 g of 2-ethylhexyloxypropylamine was mixed with 44 g of 36% hydrochloric acid and water to a total volume of 1M.
A solution was prepared, added to the above solution, and stirred for 2 hours. Potassium chloride was then added and allowed to cool to perform salting out. The precipitate was collected by filtration and washed with a small amount of water. It was dried at 50° C. to obtain 216 g of a black powder salt-forming dye represented by the following formula.
この染料は、アルコール−水系フェルトペンインキ用黒
色染料として良好であった。各種溶剤に対する溶解性は
、後記第１表に示す。This dye was good as a black dye for alcohol-water based felt pen ink. The solubility in various solvents is shown in Table 1 below.
実施例 ２
次式
で表される染料１７１ｇを３見の水に加え６０〜７０℃
で溶解後、３５〜４０℃に冷却する６次に、ジフェニル
グアニジンｔ２８ｇを３６％塩酸６９ｇと水で全容１．
２Ｊｌの溶液をつくり、先の液に加え、３５〜４０℃で
２時間攪拌する０次いで５５℃に昇温し、！１１拌した
まま室温まで冷却し、沈殿をろ取し６１の水で水洗した
。５０℃で乾燥し１次式で表される黒色粉末の造塩体染
料２６８ｇ得た。Example 2 171g of the dye represented by the following formula was added to water at 60-70°C.
After dissolving in water, cool to 35-40°C. Next, 28 g of diphenylguanidine t was dissolved in 69 g of 36% hydrochloric acid and water to a total volume of 1.
Make 2 Jl of solution, add it to the previous solution, stir at 35-40°C for 2 hours, then raise the temperature to 55°C. The mixture was cooled to room temperature while stirring in step 11, and the precipitate was collected by filtration and washed with water in step 61. After drying at 50° C., 268 g of a black powder salt-forming dye represented by the linear formula was obtained.
この染料は、ボールペンインキ用黒色染料として良好で
あった。各種溶剤に対する溶解性は、後記第１表に示す
。This dye was good as a black dye for ballpoint pen ink. The solubility in various solvents is shown in Table 1 below.
実施例 ３
次式
で表される染料１６５．４ｇを４文の水に加え６０〜７
０℃で溶解する０次に、２−エチルヘキシルアミン３８
．７ｇおよびジェタノールアミン１８．２ｇを３６％塩
酸５５ｇと水で全容ｉＪｌの溶液をつくり、先の液に加
え、２時間攪拌する０次いで食塩を加え放冷し塩析を行
う、沈殿をろ取し少量の水で水洗した。５０℃で乾燥し
、次式で表される黒色粉末の造塩体染料１９８ｇ得た。Example 3 165.4g of the dye represented by the following formula was added to 4 parts of water and 60~7
2-ethylhexylamine 38
．． Make a solution of 7g and 18.2g of jetanolamine with 55g of 36% hydrochloric acid and water, add it to the above solution and stir for 2 hours.Next, add common salt and let it stand to cool for salting out.Filter out the precipitate. and washed with a small amount of water. It was dried at 50° C. to obtain 198 g of a black powder salt-forming dye represented by the following formula.
得られり染料は、アルコールベースフェルトペンインキ
用黒色染料として良好であった。各種溶剤に対する溶解
性は、後記第１表に示す。The resulting dye was good as a black dye for alcohol-based felt pen inks. The solubility in various solvents is shown in Table 1 below.
実施例 ４
次式
％式％
で表される染料１７９ｇを２．５文の水に加え６０〜７
０℃で溶解後、３０〜３５℃に冷却しクロロホルム１１
を加える０次に、エソミンＥＴ−１５（ライオンアクゾ
社製）２８８ｇを３６％塩酸６９ｇと水で全容１．２１
の溶液をつくり、先の液に加え、２時間攪拌する０反応
混合物を分液ロートに移し、静置する。下層のクロロホ
ルム溶液を分取する。Example 4 179 g of dye represented by the following formula % was added to 2.5 grams of water and 60 to 7
After dissolving at 0°C, cool to 30-35°C and dissolve in chloroform 11.
Next, 288 g of Esomin ET-15 (manufactured by Lion Akzo) was mixed with 69 g of 36% hydrochloric acid and water to a total volume of 1.21 g.
Make a solution, add to the previous solution, and stir for 2 hours. Transfer the reaction mixture to a separating funnel and let stand. Separate the lower chloroform solution.
クロロホルム溶液を１分液ロートに移し、水１文を加え
攪拌した後分液を行い、クロロホルム溶液は更に同様の
操作を数回繰り返す。Transfer the chloroform solution to a 1-separating funnel, add 1 liter of water, stir, and separate the liquid. Repeat the same operation several times for the chloroform solution.
得られたクロロホルム溶液はロータリーエバポレーター
にてクロロホルムを回収して。Chloroform was recovered from the obtained chloroform solution using a rotary evaporator.
次式で表される黒色タール状の造塩体染料４１８ｇ得た
。418 g of a black tar-like salt-forming dye represented by the following formula was obtained.
この染料の色調及び各種溶剤に対する溶解性は、後記第
１表に示す。The color tone and solubility of this dye in various solvents are shown in Table 1 below.
得られた染料４０ｇをボールペンインキ溶剤（フェニル
グリコール：ベンジルアルコール＝４二１）６０ｇに８
０乃至９０℃で加温溶解し、セライト濾過して得た濃厚
溶液は、結晶の析出なく、経時安定性良好であった。40g of the obtained dye was added to 60g of ballpoint pen ink solvent (phenyl glycol: benzyl alcohol = 421).
The concentrated solution obtained by heating and dissolving at 0 to 90°C and filtering through Celite had good stability over time without precipitation of crystals.
実施例 ５
次式
で表される染料１８４ｇを含むウェットケーキとプライ
メンＪＭ−Ｔ（ロームアンドハース社製）２０１ｇをボ
ールミルに仕込み、５時間運転した。得られた混合物を
、５０℃で減圧乾燥して、次式で表される黒色タール状
の造塩体染料３３２ｇ得た。Example 5 A wet cake containing 184 g of a dye represented by the following formula and 201 g of Primen JM-T (manufactured by Rohm and Haas) were placed in a ball mill and operated for 5 hours. The resulting mixture was dried under reduced pressure at 50° C. to obtain 332 g of a black tar-like salt-forming dye represented by the following formula.
本品は、セロソルブ系インキ、例えばスタンプインキ用
として良好であった。各種溶剤に対する溶解性は、後記
第１表に示す。This product was good for use in cellosolve-based inks, such as stamp inks. The solubility in various solvents is shown in Table 1 below.
実施例 ６〜２０
常法および実施例１乃至５に準じて１次の如き本発明に
係る造塩体染料を得た。Examples 6 to 20 Salt-forming dyes according to the present invention as shown below were obtained according to conventional methods and Examples 1 to 5.
色調及び各種溶剤に対する溶解性は、後記第１表に示す
。The color tone and solubility in various solvents are shown in Table 1 below.
■ ・
口
渭； ９
■
ロ
ロ
■ ・
ば１
■ ・
口
♂
■
口
■ ・
口
■ “−
の
第１表（化合物溶解性）
Ｏ：可溶
［発明の効果］
本発明に係る新規なヘキサキスアゾ染料は、反応組成の
選択により、極性溶剤溶けのものから非極性溶剤溶けの
ものに至るまで幅広い溶解性が得られ、而も、黒色系の
極めて良好な色調を有し、耐水性・耐光性・溶解安定性
等きわめて良好な性質を有して、セルロース、天然又は
合成ポリアミド材料及び皮革等の着色剤として、或はま
た、石油製品の着色変性用等として、広範にして顕著な
効果を有する。■ ・口札； 9 ■ ロロ■ ・ BA1 ■ ・口♂ ■ 口■ ・口■ Table 1 (compound solubility) of “−” O: Soluble [Effect of the invention] Novel hexakisazo dye according to the present invention By selecting the reaction composition, a wide range of solubility can be obtained, ranging from those soluble in polar solvents to those soluble in non-polar solvents.In addition, it has an extremely good black color tone, and has excellent water resistance, light resistance, and It has extremely good properties such as dissolution stability, and has a wide range of remarkable effects as a coloring agent for cellulose, natural or synthetic polyamide materials, leather, etc., or for color modification of petroleum products.
更に１本発明に係る新規なヘキサキスアゾ染料のインキ
組成物も、その組成分たるヘキサキスアゾ染料の特性よ
りして、特に筆記具用、ジェット印刷用、記録計用等と
して極めて顕著な効果を有し、また、水または水溶性有
機溶剤に可溶性の、部分造塩染料（一般式（２）におい
てｍ ＜ ｎ ）を着色剤として水性インキに用いると
、造塩していない染料を用いたのに比し、筆跡の耐水性
が優れた水性インキが得られ、極めて有用である。Furthermore, the novel hexakisazo dye ink composition according to the present invention has extremely remarkable effects particularly for writing instruments, jet printing, recorders, etc. due to the properties of the hexakisazo dye as a component. When a partially salt-forming dye (m < n in general formula (2)) soluble in water or a water-soluble organic solvent is used as a coloring agent in an aqueous ink, compared to using a non-salt-forming dye, A water-based ink with excellent water resistance for handwriting is obtained and is extremely useful.
以上、要するに、本発明に係る新規なヘキサキスアゾ染
料は、凡ゆる点よりして産業利用性が多大である。In summary, the novel hexakisazo dye according to the present invention has great industrial applicability in all respects.
Claims (1)
いフェニル基）、−ＳＯ＿２−または−Ｏ−、 Ｙは、Ｈ、ＣＨ＿３、ＯＣＨ＿３、ＣｌまたはＳＯ＿３
Ｍ、 Ａ＿１及びＡ＿２は、 ▲数式、化学式、表等があります▼または▲数式、化学
式、表等があります▼ （Ｚ＿１は、Ｈ、Ｃｌ、ＣＨ＿３、ＯＨ、 ＯＣＨ＿３、ＯＣ＿２Ｈ＿５またはＳＯ＿３Ｍ、Ｚ＿２
は、Ｈ、ＣＨ＿３、ＮＯ＿２またはＣＯＯＭ）、 Ｂ＿１及びＢ＿２は、 ▲数式、化学式、表等があります▼または▲数式、化学
式、表等があります▼ （Ｚ＿３は、Ｈ、ＯＨ、ＮＨ＿２、ＣｌまたはＣＯＯＭ
、Ｚ＿４は、Ｈ、Ｃｌ、ＣＨ＿３、ＯＨ、ＯＣＨ＿３、
ＮＨ＿２、ＣＯＯＭまたはＳＯ＿３Ｍ、Ｚ＿５は、Ｈ、
Ｃ＿１〜Ｃ＿４アルキル基またはＯＨ）、 Ｍは、Ｈ、Ｎａ、Ｋ、ＬｉまたはＮＨ＿４、ｆは、０ま
たは１、 ｍは、０、１または２、 ｎは、０、１または２ を示す。 で表されるヘキサキスアゾ染料に、脂肪酸アミン類、脂
環族アミン類、芳香族アミン類または第４級アンモニウ
ム塩類を作用させることを特徴とする、一般式 ▲数式、化学式、表等があります▼・・・・（２） 式中、 Ｄは、一般式（１）で表されるヘキサキスアゾ染料の残
基を示し、 〔Ａ〕は、脂肪族アンモニウムイオン、脂環族アンモニ
ウムイオン、芳香族アンモニウムイオンまたは第４級ア
ンモニウムイオンを示し、 Ｍは、Ｈ、Ｎａ、Ｋ、ＬｉまたはＮＨ＿４を示し、 ｍは、１乃至ｎの数を示し、 ｎは、分子中に含まれるスルホン酸基及びカルボキシル
基の総数に等しい、 で表される、新規なヘキサキスアゾ染料の製造法。[Claims] General formula ▲ Numerical formulas, chemical formulas, tables, etc. ▼... (1) [In the formula, X is -CH=CH-, -CONH-, -CRH- (R is H or a phenyl group which may have a sulfonic acid group), -SO_2- or -O-, Y is H, CH_3, OCH_3, Cl or SO_3
M, A_1 and A_2 are: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ or ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (Z_1 is H, Cl, CH_3, OH, OCH_3, OC_2H_5 or SO_3M, Z_2
is H, CH_3, NO_2 or COOM), B_1 and B_2 are ▲There are mathematical formulas, chemical formulas, tables, etc.▼or▲There are mathematical formulas, chemical formulas, tables, etc.▼
, Z_4 is H, Cl, CH_3, OH, OCH_3,
NH_2, COOM or SO_3M, Z_5 is H,
C_1 to C_4 alkyl group or OH), M is H, Na, K, Li or NH_4, f is 0 or 1, m is 0, 1 or 2, n is 0, 1 or 2. There are general formulas, mathematical formulas, chemical formulas, tables, etc. that are characterized by the action of fatty acid amines, alicyclic amines, aromatic amines, or quaternary ammonium salts on the hexakisazo dye represented by ...(2) In the formula, D represents a residue of the hexakisazo dye represented by the general formula (1), and [A] is an aliphatic ammonium ion, an alicyclic ammonium ion, an aromatic ammonium ion, or Represents a quaternary ammonium ion, M represents H, Na, K, Li or NH_4, m represents a number from 1 to n, n is the total number of sulfonic acid groups and carboxyl groups contained in the molecule. A method for producing a novel hexakisazo dye, which is equal to .
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13251986A JPS62288659A (en) | 1986-06-06 | 1986-06-06 | Production of novel hexakisazo dye |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13251986A JPS62288659A (en) | 1986-06-06 | 1986-06-06 | Production of novel hexakisazo dye |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS62288659A true JPS62288659A (en) | 1987-12-15 |
Family
ID=15083217
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13251986A Pending JPS62288659A (en) | 1986-06-06 | 1986-06-06 | Production of novel hexakisazo dye |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62288659A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1775324A1 (en) * | 2000-11-16 | 2007-04-18 | Sun Chemical Corporation | Treatment of high performance pigments with etheramine dispersing salts |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2139742A (en) * | 1937-03-15 | 1938-12-13 | Kwikon Company | Service entrance device |
| JPS5748590A (en) * | 1980-09-05 | 1982-03-19 | Unic Corp | Crane with bench |
| JPS60229953A (en) * | 1984-04-28 | 1985-11-15 | Orient Kagaku Kogyo Kk | Preparation of novel tetrakisazo dye |
-
1986
- 1986-06-06 JP JP13251986A patent/JPS62288659A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2139742A (en) * | 1937-03-15 | 1938-12-13 | Kwikon Company | Service entrance device |
| JPS5748590A (en) * | 1980-09-05 | 1982-03-19 | Unic Corp | Crane with bench |
| JPS60229953A (en) * | 1984-04-28 | 1985-11-15 | Orient Kagaku Kogyo Kk | Preparation of novel tetrakisazo dye |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1775324A1 (en) * | 2000-11-16 | 2007-04-18 | Sun Chemical Corporation | Treatment of high performance pigments with etheramine dispersing salts |
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