JPH045067B2 - - Google Patents
Info
- Publication number
- JPH045067B2 JPH045067B2 JP59195471A JP19547184A JPH045067B2 JP H045067 B2 JPH045067 B2 JP H045067B2 JP 59195471 A JP59195471 A JP 59195471A JP 19547184 A JP19547184 A JP 19547184A JP H045067 B2 JPH045067 B2 JP H045067B2
- Authority
- JP
- Japan
- Prior art keywords
- calculated value
- nmr
- ethanol
- synthesis example
- crystals
- 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.)
- Expired - Lifetime
Links
- 150000002790 naphthalenes Chemical class 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 42
- 239000000243 solution Substances 0.000 description 20
- 230000015572 biosynthetic process Effects 0.000 description 16
- 238000003786 synthesis reaction Methods 0.000 description 16
- 239000000835 fiber Substances 0.000 description 13
- RQNVIKXOOKXAJQ-UHFFFAOYSA-N naphthazarin Chemical compound O=C1C=CC(=O)C2=C1C(O)=CC=C2O RQNVIKXOOKXAJQ-UHFFFAOYSA-N 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 239000012300 argon atmosphere Substances 0.000 description 12
- 239000013078 crystal Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 10
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 9
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 8
- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 238000000921 elemental analysis Methods 0.000 description 8
- 238000001819 mass spectrum Methods 0.000 description 8
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- 239000000975 dye Substances 0.000 description 6
- 238000004043 dyeing Methods 0.000 description 6
- 210000004209 hair Anatomy 0.000 description 6
- 239000000984 vat dye Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 5
- 235000000177 Indigofera tinctoria Nutrition 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000000945 filler Substances 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
- 239000002244 precipitate Substances 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- CSMWJXBSXGUPGY-UHFFFAOYSA-L sodium dithionate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)S([O-])(=O)=O CSMWJXBSXGUPGY-UHFFFAOYSA-L 0.000 description 4
- 229940075931 sodium dithionate Drugs 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- HQFIIOPDBQMRIE-UHFFFAOYSA-N 5,8-dihydroxy-2,3-dihydronaphthalene-1,4-dione Chemical compound O=C1CCC(=O)C2=C1C(O)=CC=C2O HQFIIOPDBQMRIE-UHFFFAOYSA-N 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 210000002268 wool Anatomy 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 2
- 239000000118 hair dye Substances 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 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
- 239000000203 mixture Substances 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- BRKFSNHJZDVDKY-UHFFFAOYSA-N 2-(heptylamino)-5,8-dihydroxynaphthalene-1,4-dione Chemical compound C1=CC(O)=C2C(=O)C(NCCCCCCC)=CC(=O)C2=C1O BRKFSNHJZDVDKY-UHFFFAOYSA-N 0.000 description 1
- UIVVUNVPTGYZQL-UHFFFAOYSA-N 2-(hexylamino)-5,8-dihydroxynaphthalene-1,4-dione Chemical compound C1=CC(O)=C2C(=O)C(NCCCCCC)=CC(=O)C2=C1O UIVVUNVPTGYZQL-UHFFFAOYSA-N 0.000 description 1
- MNXGOYMKQHECLJ-UHFFFAOYSA-N 5,8-dihydroxy-2-(octylamino)naphthalene-1,4-dione Chemical compound C1=CC(O)=C2C(=O)C(NCCCCCCCC)=CC(=O)C2=C1O MNXGOYMKQHECLJ-UHFFFAOYSA-N 0.000 description 1
- FTITXWKPKMETDH-UHFFFAOYSA-N 5,8-dihydroxy-2-(pentylamino)naphthalene-1,4-dione Chemical compound C1=CC(O)=C2C(=O)C(NCCCCC)=CC(=O)C2=C1O FTITXWKPKMETDH-UHFFFAOYSA-N 0.000 description 1
- ZTAVRZYAHWNEFT-UHFFFAOYSA-N 6-(heptylamino)-5,8-dihydroxy-2,3-dihydronaphthalene-1,4-dione Chemical compound O=C1CCC(=O)C2=C(O)C(NCCCCCCC)=CC(O)=C21 ZTAVRZYAHWNEFT-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- WJYIASZWHGOTOU-UHFFFAOYSA-N Heptylamine Chemical compound CCCCCCCN WJYIASZWHGOTOU-UHFFFAOYSA-N 0.000 description 1
- 229930192627 Naphthoquinone Natural products 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 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
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000543 intermediate 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
- 239000011259 mixed solution Substances 0.000 description 1
- 150000002791 naphthoquinones Chemical group 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- -1 sulfate ester Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/10—Preparations for permanently dyeing the hair
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/35—Ketones, e.g. benzophenone
- A61K8/355—Quinones
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Emergency Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Coloring (AREA)
- Cosmetics (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59195471A JPS6172063A (ja) | 1984-09-18 | 1984-09-18 | ナフタレン誘導体 |
| DE19853514092 DE3514092A1 (de) | 1984-04-20 | 1985-04-18 | Naphthalinderivate und verwendung derselben zum faerben von haar |
| GB08509909A GB2159828B (en) | 1984-04-20 | 1985-04-18 | Naphthalene derivatives and hair dye compositions containing them |
| FR8505964A FR2563215B1 (fr) | 1984-04-20 | 1985-04-19 | Derives du naphtalene et composition de teinture pour cheveux en contenant |
| US06/725,069 US4605419A (en) | 1984-04-20 | 1985-04-19 | 5,8-dihydroxy naphthalene-1,4-dione derivative and a hair dye composition containing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59195471A JPS6172063A (ja) | 1984-09-18 | 1984-09-18 | ナフタレン誘導体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6172063A JPS6172063A (ja) | 1986-04-14 |
| JPH045067B2 true JPH045067B2 (en]) | 1992-01-30 |
Family
ID=16341630
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59195471A Granted JPS6172063A (ja) | 1984-04-20 | 1984-09-18 | ナフタレン誘導体 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6172063A (en]) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3300200B2 (ja) * | 1995-06-20 | 2002-07-08 | 株式会社日立製作所 | 回転電機及び電動車両 |
| DE102015216055B4 (de) | 2015-08-21 | 2019-07-18 | Continental Automotive Gmbh | Kühlsystem für eine elektrische Maschine |
-
1984
- 1984-09-18 JP JP59195471A patent/JPS6172063A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6172063A (ja) | 1986-04-14 |
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