DE225232C - - Google Patents
Info
- Publication number
- DE225232C DE225232C DE1908225232D DE225232DA DE225232C DE 225232 C DE225232 C DE 225232C DE 1908225232 D DE1908225232 D DE 1908225232D DE 225232D A DE225232D A DE 225232DA DE 225232 C DE225232 C DE 225232C
- Authority
- DE
- Germany
- Prior art keywords
- red
- yellow
- orange
- anthraquinone
- benzoylated
- 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
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- KOJOUCAVSDKDPR-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)benzamide Chemical class C=1C=CC=2C(=O)C3=CC=CC=C3C(=O)C=2C=1NC(=O)C1=CC=CC=C1 KOJOUCAVSDKDPR-UHFFFAOYSA-N 0.000 claims description 3
- LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical compound O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 claims description 2
- 239000000984 vat dye Substances 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
- 229920000742 Cotton Polymers 0.000 description 7
- 239000007859 condensation product Substances 0.000 description 7
- ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 150000004056 anthraquinones Chemical class 0.000 description 5
- 238000004040 coloring Methods 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 240000007817 Olea europaea Species 0.000 description 4
- 239000008280 blood Substances 0.000 description 4
- 210000004369 blood Anatomy 0.000 description 4
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 235000019233 fast yellow AB Nutrition 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 3
- 241000167854 Bourreria succulenta Species 0.000 description 3
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 235000019693 cherries Nutrition 0.000 description 3
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 description 2
- SKDHHIUENRGTHK-UHFFFAOYSA-N 4-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C=C1 SKDHHIUENRGTHK-UHFFFAOYSA-N 0.000 description 2
- 244000172533 Viola sororia Species 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229910003460 diamond Inorganic materials 0.000 description 2
- 239000010432 diamond Substances 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 238000004048 vat dyeing Methods 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- MOXUBYCOZGSCES-UHFFFAOYSA-N 1-amino-2-benzoyl-4-methoxyanthracene-9,10-dione Chemical compound C(C1=CC=CC=C1)(=O)C1=C(C=2C(C3=CC=CC=C3C(C2C(=C1)OC)=O)=O)N MOXUBYCOZGSCES-UHFFFAOYSA-N 0.000 description 1
- WKLRPYQQRZSYPI-UHFFFAOYSA-N 1-amino-2-benzoylanthracene-9,10-dione Chemical compound C1=CC=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C1C(=O)C1=CC=CC=C1 WKLRPYQQRZSYPI-UHFFFAOYSA-N 0.000 description 1
- CKUQSDNUHYGJSJ-UHFFFAOYSA-N 1-aminooxyanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2ON CKUQSDNUHYGJSJ-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- RQFIRASFBSDTDA-UHFFFAOYSA-N 2-amino-1-benzoylanthracene-9,10-dione Chemical compound NC1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1C(=O)C1=CC=CC=C1 RQFIRASFBSDTDA-UHFFFAOYSA-N 0.000 description 1
- IKCLCGXPQILATA-UHFFFAOYSA-N 2-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Cl IKCLCGXPQILATA-UHFFFAOYSA-N 0.000 description 1
- YYYARFHFWYKNLF-UHFFFAOYSA-N 4-[(2,4-dimethylphenyl)diazenyl]-3-hydroxynaphthalene-2,7-disulfonic acid Chemical compound CC1=CC(C)=CC=C1N=NC1=C(O)C(S(O)(=O)=O)=CC2=CC(S(O)(=O)=O)=CC=C12 YYYARFHFWYKNLF-UHFFFAOYSA-N 0.000 description 1
- AXDJCCTWPBKUKL-UHFFFAOYSA-N 4-[(4-aminophenyl)-(4-imino-3-methylcyclohexa-2,5-dien-1-ylidene)methyl]aniline;hydron;chloride Chemical compound Cl.C1=CC(=N)C(C)=CC1=C(C=1C=CC(N)=CC=1)C1=CC=C(N)C=C1 AXDJCCTWPBKUKL-UHFFFAOYSA-N 0.000 description 1
- -1 Benzoyl-1 -amino-6-chloro- anthraquinone Chemical compound 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 235000005811 Viola adunca Nutrition 0.000 description 1
- 240000009038 Viola odorata Species 0.000 description 1
- 235000013487 Viola odorata Nutrition 0.000 description 1
- 235000002254 Viola papilionacea Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000000203 mixture Substances 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
- GVKCHTBDSMQENH-UHFFFAOYSA-L phloxine B Chemical compound [Na+].[Na+].[O-]C(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C([O-])=C(Br)C=C21 GVKCHTBDSMQENH-UHFFFAOYSA-L 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 229910001112 rose gold Inorganic materials 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical compound OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 description 1
- 229940103494 thiosalicylic acid Drugs 0.000 description 1
- SWGJCIMEBVHMTA-UHFFFAOYSA-K trisodium;6-oxido-4-sulfo-5-[(4-sulfonatonaphthalen-1-yl)diazenyl]naphthalene-2-sulfonate Chemical compound [Na+].[Na+].[Na+].C1=CC=C2C(N=NC3=C4C(=CC(=CC4=CC=C3O)S([O-])(=O)=O)S([O-])(=O)=O)=CC=C(S([O-])(=O)=O)C2=C1 SWGJCIMEBVHMTA-UHFFFAOYSA-K 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/36—Dyes with acylated amino groups
- C09B1/42—Dyes with acylated amino groups the acyl groups being residues of an aromatic carboxylic acid
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/36—Dyes with acylated amino groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/48—Anthrimides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE225232T | 1908-06-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE225232C true DE225232C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
Family
ID=485897
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT216772D Active DE216772C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1908-06-09 | ||
| DENDAT228992D Active DE228992C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1908-06-09 | ||
| DE1908225232D Expired - Lifetime DE225232C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1908-06-09 | 1908-06-09 |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT216772D Active DE216772C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1908-06-09 | ||
| DENDAT228992D Active DE228992C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1908-06-09 |
Country Status (2)
| Country | Link |
|---|---|
| DE (3) | DE225232C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
| FR (2) | FR400653A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE744305C (de) * | 1939-07-13 | 1944-06-08 | Ig Farbenindustrie Ag | Verfahren zur Herstellung von Leukoschwefelsaeureestern |
| US2691027A (en) * | 1946-08-07 | 1954-10-05 | Ciba Ltd | 1, 5-hydroxy-acylamino anthraquinones |
| DE1063301B (de) * | 1955-04-01 | 1959-08-13 | Ciba Geigy | Verfahren zur Herstellung von Farbstoffen der Anthrachinonreihe |
| DE1207529B (de) * | 1960-01-19 | 1965-12-23 | Kuhlmann Ets | Verfahren zur Herstellung von Farbstoffen |
| US3316114A (en) * | 1957-12-16 | 1967-04-25 | Ciba Ltd | Process for coloring organic products with pigment dyestuffs |
| US3439003A (en) * | 1964-03-26 | 1969-04-15 | Ciba Ltd | 1,5-bis-(2',4'-dihalo-benzamido)-4-hydroxy (and 4,8-dihydroxy)-anthraquinones |
| FR2350329A1 (fr) * | 1976-05-08 | 1977-12-02 | Bayer Ag | Procede de production de 1-acylamino-5(8)-chloranthraquinones |
-
0
- FR FR11026D patent/FR11026E/fr not_active Expired
- DE DENDAT216772D patent/DE216772C/de active Active
- DE DENDAT228992D patent/DE228992C/de active Active
-
1908
- 1908-06-09 DE DE1908225232D patent/DE225232C/de not_active Expired - Lifetime
-
1909
- 1909-03-10 FR FR400653D patent/FR400653A/fr not_active Expired
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE744305C (de) * | 1939-07-13 | 1944-06-08 | Ig Farbenindustrie Ag | Verfahren zur Herstellung von Leukoschwefelsaeureestern |
| US2691027A (en) * | 1946-08-07 | 1954-10-05 | Ciba Ltd | 1, 5-hydroxy-acylamino anthraquinones |
| DE1063301B (de) * | 1955-04-01 | 1959-08-13 | Ciba Geigy | Verfahren zur Herstellung von Farbstoffen der Anthrachinonreihe |
| US3316114A (en) * | 1957-12-16 | 1967-04-25 | Ciba Ltd | Process for coloring organic products with pigment dyestuffs |
| DE1207529B (de) * | 1960-01-19 | 1965-12-23 | Kuhlmann Ets | Verfahren zur Herstellung von Farbstoffen |
| US3439003A (en) * | 1964-03-26 | 1969-04-15 | Ciba Ltd | 1,5-bis-(2',4'-dihalo-benzamido)-4-hydroxy (and 4,8-dihydroxy)-anthraquinones |
| FR2350329A1 (fr) * | 1976-05-08 | 1977-12-02 | Bayer Ag | Procede de production de 1-acylamino-5(8)-chloranthraquinones |
Also Published As
| Publication number | Publication date |
|---|---|
| FR11026E (fr) | 1909-11-26 |
| DE216772C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | |
| DE228992C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | |
| FR400653A (fr) | 1909-08-04 |