JPS60226557A

JPS60226557A - トリスアゾ系の化合物およびトリスアゾ系の染料

トリスアゾ系の化合物およびトリスアゾ系の染料

Info

Publication number: JPS60226557A
Authority: JP; Japan
Prior art keywords: group; sulfonic acid; formula; compound; lower alkyl
Prior art date: 1984-04-25
Legal status : Granted

Application number

JP59083569A

Other languages

English (en)

Japanese (ja)

Other versions

JPH051308B2 (enrdf_load_stackoverflow

Inventor

Toshio Niwa

俊夫丹羽

Yoshiaki Kato

美明加藤

Current Assignee

Mitsubishi Chemical Corp

Original Assignee

Mitsubishi Chemical Industries Ltd

Priority date

1984-04-25

Filing date

1984-04-25

Publication date

1985-11-11

1984-04-25 Application filed by Mitsubishi Chemical Industries Ltd filed Critical Mitsubishi Chemical Industries Ltd

1984-04-25 Priority to JP59083569A priority Critical patent/JPS60226557A/ja

1985-04-09 Priority to CH1515/85A priority patent/CH663215A5/de

1985-04-09 Priority to DE3512690A priority patent/DE3512690C2/de

1985-04-09 Priority to US06/721,514 priority patent/US4645832A/en

1985-04-09 Priority to GB08509081A priority patent/GB2160883B/en

1985-11-11 Publication of JPS60226557A publication Critical patent/JPS60226557A/ja

1993-01-07 Publication of JPH051308B2 publication Critical patent/JPH051308B2/ja

Status Granted legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 title abstract description 30
125000003545 alkoxy group Chemical group 0.000 claims abstract description 15
125000000217 alkyl group Chemical group 0.000 claims abstract description 15
229910052783 alkali metal Inorganic materials 0.000 claims abstract description 8
150000001340 alkali metals Chemical class 0.000 claims abstract description 8
229910052801 chlorine Inorganic materials 0.000 claims abstract description 6
229910052731 fluorine Inorganic materials 0.000 claims abstract description 3
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical group C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims abstract 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
125000000542 sulfonic acid group Chemical group 0.000 claims description 12
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims description 2
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
238000004043 dyeing Methods 0.000 abstract description 31
239000000835 fiber Substances 0.000 abstract description 28
239000000975 dye Substances 0.000 abstract description 27
229920000728 polyester Polymers 0.000 abstract description 14
-1 methoxy, phenoxy Chemical group 0.000 abstract description 10
238000005859 coupling reaction Methods 0.000 abstract description 7
238000006193 diazotization reaction Methods 0.000 abstract description 5
150000001989 diazonium salts Chemical class 0.000 abstract description 3
125000001931 aliphatic group Chemical group 0.000 abstract description 2
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 abstract 2
AKQBRLCZNUDALS-UHFFFAOYSA-N acetylsulfamic acid Chemical compound CC(=O)NS(O)(=O)=O AKQBRLCZNUDALS-UHFFFAOYSA-N 0.000 abstract 1
125000003277 amino group Chemical group 0.000 abstract 1
239000012736 aqueous medium Substances 0.000 abstract 1
238000006482 condensation reaction Methods 0.000 abstract 1
239000006185 dispersion Substances 0.000 abstract 1
239000000463 material Substances 0.000 abstract 1
238000002360 preparation method Methods 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
229920003043 Cellulose fiber Polymers 0.000 description 17
239000002253 acid Substances 0.000 description 11
238000000034 method Methods 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
239000000986 disperse dye Substances 0.000 description 8
239000004744 fabric Substances 0.000 description 7
239000000047 product Substances 0.000 description 7
230000008878 coupling Effects 0.000 description 6
238000010168 coupling process Methods 0.000 description 6
229920000742 Cotton Polymers 0.000 description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
239000011230 binding agent Substances 0.000 description 3
239000006172 buffering agent Substances 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000000985 reactive dye Substances 0.000 description 3
239000011734 sodium Substances 0.000 description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
229920000297 Rayon Polymers 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 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
VMKJWLXVLHBJNK-UHFFFAOYSA-N cyanuric fluoride Chemical compound FC1=NC(F)=NC(F)=N1 VMKJWLXVLHBJNK-UHFFFAOYSA-N 0.000 description 2
238000001035 drying Methods 0.000 description 2
239000003792 electrolyte Substances 0.000 description 2
239000010446 mirabilite Substances 0.000 description 2
239000000203 mixture Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
238000005406 washing Methods 0.000 description 2
101100283604 Caenorhabditis elegans pigk-1 gene Proteins 0.000 description 1
244000025254 Cannabis sativa Species 0.000 description 1
235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 1
235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
125000003282 alkyl amino group Chemical group 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
AGSPXMVUFBBBMO-UHFFFAOYSA-N beta-aminopropionitrile Chemical compound NCCC#N AGSPXMVUFBBBMO-UHFFFAOYSA-N 0.000 description 1
239000000872 buffer Substances 0.000 description 1
235000009120 camo Nutrition 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
235000005607 chanvre indien Nutrition 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
238000007796 conventional method Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000011487 hemp Substances 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
229920002239 polyacrylonitrile Polymers 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000001103 potassium chloride Substances 0.000 description 1
235000011164 potassium chloride Nutrition 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
239000002964 rayon Substances 0.000 description 1
238000005185 salting out Methods 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 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
238000010186 staining Methods 0.000 description 1
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
210000004243 sweat Anatomy 0.000 description 1
ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
210000002268 wool Anatomy 0.000 description 1