JPS6195074A

JPS6195074A - ナフタレン誘導体

ナフタレン誘導体

Info

Publication number: JPS6195074A
Authority: JP; Japan
Prior art keywords: naphthalene derivative; water; present; fibers; benzylamino
Prior art date: 1984-10-16
Legal status : Granted

Application number

JP59216560A

Other languages

English (en)

Japanese (ja)

Other versions

JPH046224B2 (enrdf_load_stackoverflow

Inventor

Masashi Kikuchi

正志菊地

Masahiro Matsuoka

松岡　昌弘

Current Assignee

Shiseido Co Ltd

Original Assignee

Shiseido Co Ltd

Priority date

1984-10-16

Filing date

1984-10-16

Publication date

1986-05-13

1984-10-16 Application filed by Shiseido Co Ltd filed Critical Shiseido Co Ltd

1984-10-16 Priority to JP59216560A priority Critical patent/JPS6195074A/ja

1985-04-18 Priority to GB08509909A priority patent/GB2159828B/en

1985-04-18 Priority to DE19853514092 priority patent/DE3514092A1/de

1985-04-19 Priority to US06/725,069 priority patent/US4605419A/en

1985-04-19 Priority to FR8505964A priority patent/FR2563215B1/fr

1986-05-13 Publication of JPS6195074A publication Critical patent/JPS6195074A/ja

1992-02-05 Publication of JPH046224B2 publication Critical patent/JPH046224B2/ja

Status Granted legal-status Critical Current

Links

150000002790 naphthalenes Chemical class 0.000 title claims description 11
239000000126 substance Substances 0.000 claims description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 8
239000000975 dye Substances 0.000 abstract description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 7
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 abstract description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract description 6
239000003638 chemical reducing agent Substances 0.000 abstract description 5
150000001875 compounds Chemical class 0.000 abstract description 5
YMRPLQOGTCQPLI-UHFFFAOYSA-N 2-(benzylamino)-5,8-dihydroxynaphthalene-1,4-dione Chemical compound C=1C(=O)C=2C(O)=CC=C(O)C=2C(=O)C=1NCC1=CC=CC=C1 YMRPLQOGTCQPLI-UHFFFAOYSA-N 0.000 abstract description 3
239000003513 alkali Substances 0.000 abstract description 3
238000010992 reflux Methods 0.000 abstract description 3
229910000029 sodium carbonate Inorganic materials 0.000 abstract description 3
CSMWJXBSXGUPGY-UHFFFAOYSA-L sodium dithionate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)S([O-])(=O)=O CSMWJXBSXGUPGY-UHFFFAOYSA-L 0.000 abstract description 3
229940075931 sodium dithionate Drugs 0.000 abstract description 3
239000000543 intermediate Substances 0.000 abstract description 2
239000011259 mixed solution Substances 0.000 abstract description 2
239000000049 pigment Substances 0.000 abstract description 2
239000000463 material Substances 0.000 abstract 1
238000002360 preparation method Methods 0.000 abstract 1
235000017550 sodium carbonate Nutrition 0.000 abstract 1
239000000835 fiber Substances 0.000 description 13
230000015572 biosynthetic process Effects 0.000 description 7
239000000243 solution Substances 0.000 description 7
238000003786 synthesis reaction Methods 0.000 description 7
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
210000004209 hair Anatomy 0.000 description 6
239000000984 vat dye Substances 0.000 description 6
238000004043 dyeing Methods 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
235000000177 Indigofera tinctoria Nutrition 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
229940097275 indigo Drugs 0.000 description 4
COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
239000012300 argon atmosphere Substances 0.000 description 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
239000013078 crystal Substances 0.000 description 3
RQNVIKXOOKXAJQ-UHFFFAOYSA-N naphthazarin Chemical compound O=C1C=CC(=O)C2=C1C(O)=CC=C2O RQNVIKXOOKXAJQ-UHFFFAOYSA-N 0.000 description 3
239000000047 product Substances 0.000 description 3
210000002268 wool Anatomy 0.000 description 3
GPUWFTXJYWUQQT-UHFFFAOYSA-N 6-(benzylamino)-5,8-dihydroxy-2,3-dihydronaphthalene-1,4-dione Chemical compound OC=1C=2C(=O)CCC(=O)C=2C(O)=CC=1NCC1=CC=CC=C1 GPUWFTXJYWUQQT-UHFFFAOYSA-N 0.000 description 2
101150041968 CDC13 gene Proteins 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
238000000921 elemental analysis Methods 0.000 description 2
239000000118 hair dye Substances 0.000 description 2
QTWZICCBKBYHDM-UHFFFAOYSA-N leucomethylene blue Chemical compound C1=C(N(C)C)C=C2SC3=CC(N(C)C)=CC=C3NC2=C1 QTWZICCBKBYHDM-UHFFFAOYSA-N 0.000 description 2
238000001819 mass spectrum Methods 0.000 description 2
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
239000007800 oxidant agent Substances 0.000 description 2
239000004753 textile Substances 0.000 description 2
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
229930192627 Naphthoquinone Natural products 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000001000 anthraquinone dye Substances 0.000 description 1
125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000000945 filler Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
239000000203 mixture Substances 0.000 description 1
150000002791 naphthoquinones Chemical group 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
239000012286 potassium permanganate Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
150000004053 quinones Chemical class 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000002453 shampoo Substances 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000010186 staining Methods 0.000 description 1
-1 sulfate ester Chemical class 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1