US469329A - Arthur weinberg - Google Patents
Arthur weinberg Download PDFInfo
- Publication number
- US469329A US469329A US469329DA US469329A US 469329 A US469329 A US 469329A US 469329D A US469329D A US 469329DA US 469329 A US469329 A US 469329A
- Authority
- US
- United States
- Prior art keywords
- kilos
- read
- arthur
- word
- weinberg
- 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
- 238000004519 manufacturing process Methods 0.000 description 6
- JLTDJTHDQAWBAV-UHFFFAOYSA-N Dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- OBCSAIDCZQSFQH-UHFFFAOYSA-N 2-methyl-1,4-phenylenediamine Chemical group CC1=CC(N)=CC=C1N OBCSAIDCZQSFQH-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N Diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 2
- 239000001263 FEMA 3042 Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- GUAWMXYQZKVRCW-UHFFFAOYSA-N N,2-dimethylaniline Chemical compound CNC1=CC=CC=C1C GUAWMXYQZKVRCW-UHFFFAOYSA-N 0.000 description 2
- JDEJGVSZUIJWBM-UHFFFAOYSA-N N,N,2-trimethylaniline Chemical class CN(C)C1=CC=CC=C1C JDEJGVSZUIJWBM-UHFFFAOYSA-N 0.000 description 2
- KMUONIBRACKNSN-UHFFFAOYSA-N Potassium dichromate Chemical compound [K+].[K+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KMUONIBRACKNSN-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229940033123 Tannic Acid Drugs 0.000 description 2
- LRBQNJMCXXYXIU-NRMVVENXSA-N Tannic acid Chemical compound OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-NRMVVENXSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000003518 caustics Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 235000011167 hydrochloric acid Nutrition 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 150000002832 nitroso derivatives Chemical class 0.000 description 2
- XKLJHFLUAHKGGU-UHFFFAOYSA-N nitrous amide Chemical compound ON=N XKLJHFLUAHKGGU-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 229940072033 potash Drugs 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 235000015320 potassium carbonate Nutrition 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- 239000001117 sulphuric acid Substances 0.000 description 2
- 235000015523 tannic acid Nutrition 0.000 description 2
- 229920002258 tannic acid Polymers 0.000 description 2
- UPKAWFACSJWKND-ZXFFUEEESA-J tetrasodium;(6E)-4-amino-6-[[4-[4-[(2Z)-2-(8-amino-1-oxo-5,7-disulfonatonaphthalen-2-ylidene)hydrazinyl]-3-methoxyphenyl]-2-methoxyphenyl]hydrazinylidene]-5-oxonaphthalene-1,3-disulfonate Chemical compound [Na+].[Na+].[Na+].[Na+].C\1=CC2=C(S([O-])(=O)=O)C=C(S([O-])(=O)=O)C(N)=C2C(=O)C/1=N/NC(C(OC)=C1)=CC=C1C1=CC=C(N\N=C\2C(C3=C(N)C(=CC(=C3C=C/2)S([O-])(=O)=O)S([O-])(=O)=O)=O)C(OC)=C1 UPKAWFACSJWKND-ZXFFUEEESA-J 0.000 description 2
- KUUVQVSHGLHAKZ-UHFFFAOYSA-N thionine Chemical compound C=1C=CC=CSC=CC=1 KUUVQVSHGLHAKZ-UHFFFAOYSA-N 0.000 description 2
- 150000000552 thionines Chemical class 0.000 description 2
- DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical compound [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
- C07D279/14—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems
- C07D279/18—[b, e]-condensed with two six-membered rings
Definitions
- This invention has for its object the production of blue dye-stuffs.
- a patent having the same object has been taken in France bearing the number 211,821, of June 12, 1891.
- the present specification relates to a process for obtaining the toluthianines, of which the following is an example.
- the new dyestuffs are distinguished by their great intensity.
- NOC II NHC II hydrochlorate of paranitrosomanomethyltoluidine
- otoluidine instead of monomethylotoluidine being used as the second component, other amines may be employed, such as otoluidine, dimethylaniline, or diethylaniline.
- the new dyestuff herein described being a thionine derivative of secondary paratoluylenediamine, which is a dark-green crystalline powder easily soluble in Water and in spirit, dissolving in alcohol with a blue color, which turns into red if caustic sodais added, and dissolving in strong sulphuric acid with a pure green shade.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Treatment Of Fiber Materials (AREA)
- Cosmetics (AREA)
Description
UNITED STATES PATENT ()EEIcE.
ARTHUR \VEINBERG, OF MAINKUR, ASSIGNOR TO LEOPOLD CASSELLA & (30., OF FRANKFORT-ON-THE-MAIN, GERMANY.
BLUE DYE.
SPECIFICATION forming part of Letters Patent No. 469,329, dated February 23, 1892. Application filed July 27,1891. Serial No. 400,867. (Speeimens.) Patented in France June 12. 1891. No. 211,821.
To 60% whom it may concern:
Be it known that I, ARTHUR WEINBERG, a citizen of the Empire of Germany, and a resident of Mainkur, near Frankfort-on-the-Maiu, have invented new and useful Improvements in the Production of Blue Dye-Stuffs, of which the following is a specification.
This invention has for its object the production of blue dye-stuffs. A patent having the same object has been taken in France bearing the number 211,821, of June 12, 1891.
The known methods of producing thionine dye-stuffs from dimethylaniline cannot be used for the production of analogous derivatives of dimethylotoluidine, because the latter cannot be transformed into a nitroso compound.
The present specification relates to a process for obtaining the toluthianines, of which the following is an example. The new dyestuffs are distinguished by their great intensity.
Example: 16.5 kilos of the nitrosamine of monamethyl (or ethyl) otoluidine are dis solved at about 5 centigrade in one hundred and fifty kilos of strong muriatic acid. After standing some hours the clear solution, which then contains the hydrochlorate of paranitrosomanomethyltoluidine, (NOC II NHC II is diluted with water and cooled with ice. It is reduced by means of thirteen kilos of zincdust. As soon as the liquid has become colorless, the free mineral acid is neutralized and 24.8 kilos of thiosulphate of soda and shortly afterward ten kilos of bichromate of potash are added. Then the solution of 17.2 kilos of hydrochlorateof monomethylorthotoluidine is introduced. The oxidation is performed by adding first one hundred and twenty kilos of chloride of zinc, and then thirty kilos of hichromate of potash. The liquid is heated to the boil. The coloring-matter is separated from the residue, which contains the chrome. It forms small green crystals. It dyes on cotton mordanted with tannic acid a pure blue.
Its chemical constitution is the following:
OH. a d T In this example, instead of monomethylotoluidine being used as the second component, other amines may be employed, such as otoluidine, dimethylaniline, or diethylaniline.
Having now described the nature of my invention, what I claim as new, and desire to secure by Letters Patent, is-
The new dyestuff herein described, being a thionine derivative of secondary paratoluylenediamine, which is a dark-green crystalline powder easily soluble in Water and in spirit, dissolving in alcohol with a blue color, which turns into red if caustic sodais added, and dissolving in strong sulphuric acid with a pure green shade.
In testimony whereof I have signed my name to this specification in the presence of two subscribing witnesses.
ARTHUR VEINBERG.
\Vitnesses:
V ALVESTO S. IIooUE,
J EAN GRUND.
oorr'ections in Letters Patent No nimal/.9.
It is hereby certified that in Letters Patent No. 469,329, granted February 23, 1892, upon the application of Arthur Weinberg, of Mainkur, Germany, for an improvement in Blue Dyes, errors appear in the printed specification requiring correction as follows: In line 15 the word diinethylotoluidine should read dimethylorthotoZnicline in line 19 the word toluthianines should read tolnthionines in line 24: the word monamethyl should read monomethyl, same line the Word otoluidine should read orthotol'nidine in lines 28-29 the Word paranitrosoinanoniethyltoluidine should read paranitrosomonomethyltolniciine; in lines 54-55 the word monomethylotoluidine. should read mononiethylorthotolnidine; and in lines 56-57 the the word otoluidine should read orthotolnidine; and that the Letters Patent should be read with these corrections therein that the same may conform to the record of the case in the Patent Office.
Signed, countersigned, and sealed this 24th day of May, A. D. 1892.
CYRUS BUSSEY, Assistant Secretary of the Interim".
[SEAL.]
Oountersigned:
N. 'L. FROTHINGHAM,
Acting Commissioner of Patents.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US469329A true US469329A (en) | 1892-02-23 |
Family
ID=2538189
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US469329D Expired - Lifetime US469329A (en) | Arthur weinberg |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US469329A (en) |
-
0
- US US469329D patent/US469329A/en not_active Expired - Lifetime
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US469329A (en) | Arthur weinberg | |
| US1565229A (en) | Georg kalischer | |
| US2225476A (en) | Water soluble oxazine dyestuff | |
| US688885A (en) | Brown sulfur dye and process of making same. | |
| US579773A (en) | Christian rudolph | |
| US532125A (en) | Aethue weinbeeg | |
| US2777855A (en) | Amides of hydroxybenzotriazole carboxylic acids | |
| DE742326C (en) | Process for the production of Kuepen dyes of the fluoranthene series | |
| US2493975A (en) | Trisazo-dyestuffs | |
| US225108A (en) | Heineich caeo | |
| US615497A (en) | Christopher ris and charles simon | |
| US515100A (en) | Arthur weinberg | |
| US404309A (en) | Jakob schmid | |
| US423970A (en) | Moeitz ulrich | |
| US375848A (en) | On-the-main | |
| US1032734A (en) | Products obtainable from 4,6-diamino-1.3-xylene and process of making. | |
| US282836A (en) | August bernthsen | |
| US415258A (en) | Fabriken | |
| US606295A (en) | Blue azin dye and process of making same | |
| US888852A (en) | Brown vat dye. | |
| US679221A (en) | Black polyazo dye and process of making same. | |
| US575904A (en) | Christopher ris | |
| US521985A (en) | Sohaft fur anilin fabrikation | |
| US468539A (en) | Gesellschaft fur anilin fabrikation | |
| US636066A (en) | Black cotton dye. |