US462824A - Gesellschaft fur anilin fabrikation - Google Patents
Gesellschaft fur anilin fabrikation Download PDFInfo
- Publication number
- US462824A US462824A US462824DA US462824A US 462824 A US462824 A US 462824A US 462824D A US462824D A US 462824DA US 462824 A US462824 A US 462824A
- Authority
- US
- United States
- Prior art keywords
- dye
- gesellschaft fur
- blue
- anilin fabrikation
- acid
- 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
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 title 2
- 239000000975 dye Substances 0.000 description 12
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-Naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 10
- JRBJSXQPQWSCCF-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine Chemical compound C1=C(N)C(OC)=CC(C=2C=C(OC)C(N)=CC=2)=C1 JRBJSXQPQWSCCF-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- 150000004992 toluidines Chemical class 0.000 description 10
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-Naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 6
- 229920000742 Cotton Polymers 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000001117 sulphuric acid Substances 0.000 description 6
- 235000011149 sulphuric acid Nutrition 0.000 description 6
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical compound OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000000987 azo dye Substances 0.000 description 4
- 238000004043 dyeing Methods 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 229940108066 Coal Tar Drugs 0.000 description 2
- HJEINPVZRDJRBY-UHFFFAOYSA-N Disul Chemical compound OS(=O)(=O)OCCOC1=CC=C(Cl)C=C1Cl HJEINPVZRDJRBY-UHFFFAOYSA-N 0.000 description 2
- BHAAPTBBJKJZER-UHFFFAOYSA-N P-Anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000011280 coal tar Substances 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 150000008049 diazo compounds Chemical class 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000009967 direct dyeing Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-M nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-N nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- -1 sulpho Chemical class 0.000 description 2
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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
Definitions
- GUSTAV SCHULTZ OF BERLlN, GERMANY, ASSIGNOR TO THE AGTIEN- GESELLSCHAFT FUR ANILIN FABRIKATION, OF SAME PLACE.
- the invention consists in a process of obtaining blue dye-stuffs from tetrazo-ditolyl' and naphthylamine, as will now be fully described.
- This diazo compound may be converted by heating with nitrous acid into a tetrazo compound, which latter when combined with phenols, amines, or their sulpho or carbo acids in a well-known manner produces dyestuifs adapted for dyeingandprinting.
- tetrazo compound which latter when combined with phenols, amines, or their sulpho or carbo acids in a well-known manner produces dyestuifs adapted for dyeingandprinting.
- Example 1.10.9 kilos of toluidine are converted in a well-known manner into a tetrazo compound, the solution of which is combined with a solution of 7.5 kilos of a salt of alphanaphthylamine.
- the compound is allowed to stand for some time and is afterward acidulated with hydrochloric acid and again diazotized by treatment with nitrite of soda.
- the tetrazo compound thus obtained is now combined with an alkaline solution of forty (i0) kilos of a soda salt of alpha-naphthol disulpho-acid D. such as is described in Letters Patent of the United States No. 333,034.
- After standing for some hours the mixture is heated to boiling and the resulting dye-stuff is salted out, filtered, and dried.
- the product is a coloring matter which dyes unmordanted cotton a deep-blue violet.
- Example 2 If the naphthol disulpho-acid D is replaced by alpha-naphthol disulphoacid E, which is described in Letters Patent of the United States No. 105,938, a dye-stuff is obtained that is substantially like that described in reference to example 1 and has substantially the same properties.
- Example 3 Instead of toluidine, dianisidine may be employed in the process, as described in reference to example 1. In this case 17.1 kilos of sulphate of dianisidine are used; otherwise the mode of proceeding remains the same as described in reference to said example 1. The dye-stuif obtained dyes unmordanted cotton a fine blue-green shade.
- Escmnple .i:.-Il1Sh(- ⁇ Ftd of toluidine, as described in example 2, dianisidine may also be employed, the results being the same.
- Example 5 If instead of toluidine, as described in example 1, diphenititine is used, a dye-stun. is obtained that differs but little from the dye-stuff obtained according to example 3.
- Example 6 A like result is obtained if diphenylidine is used-instead of'toluidiue, as described in example 2.
- hexa'azo dyes are generally soluble in water and sulphuric acid and insoluble in alcohol. 'lheydissolve blue in sulphuric acid and they are not readily affected by air and light.
- dianisidine and diphenititine I mean either a methyl or ethyl ether of diamidodi-phenol.
- dianisidine referred to is meant the dimethyl other of diamido diphenol OCH Crusi NH,
- diphcnititine referred to is 100 meant the diethyl ether of diamido diphenol 00 u. o u J NH 5 C H O I described by Knecht in his Work on the dyestuffs derived from coal-tar.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
UNTTE STATES PATENT OFFICE.
GUSTAV SCHULTZ, OF BERLlN, GERMANY, ASSIGNOR TO THE AGTIEN- GESELLSCHAFT FUR ANILIN FABRIKATION, OF SAME PLACE.
BLUE AZO DYE.
SPECIFICATION forming part of Letters Patent No. 462,824, dated November 10, 181.
Application filed June 4, 1890x fierial No. 354.260. (Specimens) Patented in Germany April 20, 1890, No. 57,444; in England May 5,1890, No. 6,932, and in France May 12,1890,N0.205,615.
T0 at whom it may concern.-
Be it known that I, GUSTAV SCHULTZ, chemist, a subject of the King of Prussia, residing at Berlin, Prussia, German Empire, have invented certain new and useful Improvements in the Production of New Blue Dye-Stuffs, (for which Letters Patent have been granted in Germany under date of April 20, 1890, No. 57,441; in France, dated May 12, 1890, No. 205,615, and in Great Britain, dated May 5, 1890, No. 6,932,) and I do hereby declare the following to be a full, clear, and exact description of the invention, such as will enable others skilled in the art to which it appertains to make and use the same.
The invention consists in a process of obtaining blue dye-stuffs from tetrazo-ditolyl' and naphthylamine, as will now be fully described.
By combining one molecule of tetrazo-ditolyl with one molecule of naphthylamine a product having the following chemical formula is obtained:
This diazo compound may be converted by heating with nitrous acid into a tetrazo compound, which latter when combined with phenols, amines, or their sulpho or carbo acids in a well-known manner produces dyestuifs adapted for dyeingandprinting. These dye-studs possess the valuable property of directly dyeing cottonthat is to say, they have the property of dyeing cotton without the use of a mordantand possess, besides this, the property of being unaffected by the action of light and air.
The following examples will clearly show the manner of carrying out my invention:
Example 1.10.9 kilos of toluidine are converted in a well-known manner into a tetrazo compound, the solution of which is combined with a solution of 7.5 kilos of a salt of alphanaphthylamine. The compound is allowed to stand for some time and is afterward acidulated with hydrochloric acid and again diazotized by treatment with nitrite of soda. The tetrazo compound thus obtained is now combined with an alkaline solution of forty (i0) kilos of a soda salt of alpha-naphthol disulpho-acid D. such as is described in Letters Patent of the United States No. 333,034. After standing for some hours the mixture is heated to boiling and the resulting dye-stuff is salted out, filtered, and dried. The product is a coloring matter which dyes unmordanted cotton a deep-blue violet.
Example 2.If the naphthol disulpho-acid D is replaced by alpha-naphthol disulphoacid E, which is described in Letters Patent of the United States No. 105,938, a dye-stuff is obtained that is substantially like that described in reference to example 1 and has substantially the same properties.
Example 3.Instead of toluidine, dianisidine may be employed in the process, as described in reference to example 1. In this case 17.1 kilos of sulphate of dianisidine are used; otherwise the mode of proceeding remains the same as described in reference to said example 1. The dye-stuif obtained dyes unmordanted cotton a fine blue-green shade.
Escmnple .i:.-Il1Sh(-}Ftd of toluidine, as described in example 2, dianisidine may also be employed, the results being the same.
Example 5.If instead of toluidine, as described in example 1, diphenititine is used, a dye-stun. is obtained that differs but little from the dye-stuff obtained according to example 3.
Example 6.A like result is obtained if diphenylidine is used-instead of'toluidiue, as described in example 2.
The above described hexa'azo dyes are generally soluble in water and sulphuric acid and insoluble in alcohol. 'lheydissolve blue in sulphuric acid and they are not readily affected by air and light.
13y dianisidine and diphenititine I mean either a methyl or ethyl ether of diamidodi-phenol. Ilenceby the dianisidine referred to is meant the dimethyl other of diamido diphenol OCH Crusi NH,
NH, i con,
and by the diphcnititine referred to is 100 meant the diethyl ether of diamido diphenol 00 u. o u J NH 5 C H O I described by Knecht in his Work on the dyestuffs derived from coal-tar.
Having now'described my invention, What 10 I claim is 1. The process of obtaining blue direct-dyeing dye-stuffs, which consists in combining one molecule of a tetrazo salt substantially such as described with one molecule of al- 15 pha naphthylamine, again diazotizing the compound, and combining with the resultant product two molecules of an alpha-napththol disulpho-acid, as 'set forth. 7
2. The herein-described blue heXa-azo dyes derived from one molecule of toluidine or anisidine, one molecule of alpha-naphthylamine, i
and two molecules of an alpha-n'aphthol disul' pho-acid, said dyes being insoluble 1n alcohol,-
readily soluble in water and sulphuric acid, and are not readily affected by air and light-1 In testimony whereof I affix my signature in presence of two witnesses.
. GUSTAV SCHULTZ.
Witnesses:
CARL 'FEHLERT, ADOLF DEMELIUS.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US462824A true US462824A (en) | 1891-11-10 |
Family
ID=2531696
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US462824D Expired - Lifetime US462824A (en) | Gesellschaft fur anilin fabrikation |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US462824A (en) |
-
0
- US US462824D patent/US462824A/en not_active Expired - Lifetime
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US462824A (en) | Gesellschaft fur anilin fabrikation | |
| US3457301A (en) | Disazomethine pigments | |
| US2777855A (en) | Amides of hydroxybenzotriazole carboxylic acids | |
| US2136135A (en) | Pseudo-azimido-benzene-amino-acyloacetic acid esters | |
| US515897A (en) | Johann jakob brack | |
| US2171364A (en) | Azo dyes | |
| US2182347A (en) | Azo compound | |
| US482106A (en) | Moritz ulrich and johannes bammann | |
| US423970A (en) | Moeitz ulrich | |
| US468539A (en) | Gesellschaft fur anilin fabrikation | |
| US1056493A (en) | Black trisazo dyes. | |
| US602637A (en) | Werke | |
| US2001526A (en) | Azo dyes and method for their preparation | |
| US646711A (en) | Black azo dye and process of making same. | |
| US458284A (en) | Werke | |
| US523809A (en) | Carl duisberg and philipp ott | |
| US2148146A (en) | Diazo compounds | |
| US456628A (en) | Carl alexander martius | |
| US613646A (en) | Ignaz rosenberg and friedrich krecke | |
| US501160A (en) | Benfabriken | |
| US532479A (en) | Karl pathe and oscar dressel | |
| US560448A (en) | Arthur weinberg | |
| US2199003A (en) | Diazo derivatives of guantotl | |
| US2185152A (en) | Diazo derivatives of gtjanidyl | |
| US594123A (en) | On-the-main |