US523809A - Carl duisberg and philipp ott - Google Patents
Carl duisberg and philipp ott Download PDFInfo
- Publication number
- US523809A US523809A US523809DA US523809A US 523809 A US523809 A US 523809A US 523809D A US523809D A US 523809DA US 523809 A US523809 A US 523809A
- Authority
- US
- United States
- Prior art keywords
- philipp
- ott
- dye
- cotton
- fiber
- 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
- 229920000742 Cotton Polymers 0.000 description 9
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 8
- 239000000835 fiber Substances 0.000 description 8
- 239000000975 dye Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- 229950011260 betanaphthol Drugs 0.000 description 4
- 238000004043 dyeing Methods 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 3
- 235000002639 sodium chloride Nutrition 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 2
- QRDZSRWEULKVNW-UHFFFAOYSA-N 6-hydroxy-2-oxo-1h-quinoline-4-carboxylic acid Chemical compound C1=C(O)C=C2C(C(=O)O)=CC(=O)NC2=C1 QRDZSRWEULKVNW-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 2
- OKAUOXITMZTUOJ-UHFFFAOYSA-N 7-aminonaphthalene-2-sulfonic acid Chemical compound C1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 OKAUOXITMZTUOJ-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000982 direct dye Substances 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/02—Disazo dyes
- C09B35/039—Disazo dyes characterised by the tetrazo component
- C09B35/04—Disazo dyes characterised by the tetrazo component the tetrazo component being a benzene derivative
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/916—Natural fiber dyeing
- Y10S8/918—Cellulose textile
Definitions
- Our invention relates to the production of 2 5 azo dyes on the fiber and vdepends on a peculiar property of certain coloring-matters which are obtained for instance by combining one molecular proportion of tetrazotized paradiamins (as forexample benzidin,to1idin, 0 called Oleves alpha naphthylamin mono sulfo dianisidin, diamidodiphenylenoxid and so on) with two molecular proportions of the so acid (beta or delta) which correspond with the formula: NH
- tetrazotized paradiamins as forexample benzidin,to1idin, 0 called Oleves alpha naphthylamin mono sulfo dianisidin, diamidodiphenylenoxid and so on
- so acid beta or delta
- Such or similar dye-stuffs when fixed on the fiber, can be further diazotized, and the resulting diazo or tetrazochlorids (which owing to their insolubility remain fixed on the fiber) can be directly combined with the known dye stuff components (amins, phenols or sulfo or carboxylic acids thereof), and thus shades can be produced of high intensity and great fastness. Otherwise these dye-stufis, when diazotized on fiber, can be treated with a solution of sodium carbonate in water, by means of which very fast brown shades are produced.
- the cotton which is now dyed bluish-red, is washed carefully with cold water and then introduced in a solution of 0.3 kilo, by weight, of sodium nitrite in two hundred and fifty kilos, by weight, of cold water acidulated with 0.9 kilo, by weight, of hydrochloric acid (20 Baum).
- the dye-stufi employed in the foregoing example can be replaced by analogous products from other tetrazo salts or from Oleves delta acid or by similar substantive dye-stuffs derived from the said Oleves acids (wlth the exception however of the dye-stuff from tetrazodiphenylchlorid and Oleves beta acid, which dye-stuff cannot be dyed owing to Its insolubility in water), and the above employed beta naphthol may be replaced by other suitable dye-stuff components (developers) shades being produced which in general are from violet to blue and black. The best shades, however, are obtained by employing beta-napbtol.
- the process herein before defined is of a great technical value 25 as the shades produced on the fiber in the aforesaid manner or in an analogous or similar way possess very great fastness to soaping and to the action of alkalies and acids.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
15 Hungary, No. 53,601 and UNITED: STATES PATENT ()FFIcE;
OARLYDUISBERG AND PHILIPP err, on ELBERFELD, GERMANY, ASSIGNORS TOTHE FARBENFABRIKEN,VORMALS FR. BAYER & 00., or SAME PLACE.
PROCESS OF DYEING.
SPECIFICATION forming part of Letters eaten No. 523,809, dated July 31,1894.
' Application filed April 21, 1894.. Serial No.
508,506. (Specimcns.) Patented in Germany September 15, 1891, Z; in
England December 28, 1891, No. 22,641; in Belgium December 31, 1891, No- 97,665,' in Italy January 9, 1892, XXVI 30,988, LX, 468; in France March 21, 1892, No. 78,592.
N- 213,971,2u1d in Austria-Hungary January 29, 1893, No. 53,601 and 'To all whom it may concern: Be it known that we, CARL DUISBERG and PHILIPP OTT, chemists and doctors of'philosophy, subjects of the'Emperorof Germany, residing at Elberfeld, Prussia, Germany, (assignors to the FARBENFABRIKEN, VORMALS FR. BAYER & 00., Elberfeld, Germany,) have invented certain new' and useful Improvements in Processes of Dyeing, (for which the to aforesaid FARBENFABRIKEN has already obtained Letters Patent in Germany, N 0. 65,262, dated September 15, 1891; in France, No. 213,971, dated March 21, 1892; in England, No. 22,641, dated December 28, 1891; in Austria- No. 78,592, dated January 29, 1893; in Italy XXVI, 30,988, LX, 468, dated January 9, 1892, and in Belgium, No. 97,665, dated December 31, 1891;) and we 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.
Our invention relates to the production of 2 5 azo dyes on the fiber and vdepends on a peculiar property of certain coloring-matters which are obtained for instance by combining one molecular proportion of tetrazotized paradiamins (as forexample benzidin,to1idin, 0 called Oleves alpha naphthylamin mono sulfo dianisidin, diamidodiphenylenoxid and so on) with two molecular proportions of the so acid (beta or delta) which correspond with the formula: NH
and
latter case coloring matters are obtained, which, for example, are illustrated by the following combination:
Such or similar dye-stuffs, when fixed on the fiber, can be further diazotized, and the resulting diazo or tetrazochlorids (which owing to their insolubility remain fixed on the fiber) can be directly combined with the known dye stuff components (amins, phenols or sulfo or carboxylic acids thereof), and thus shades can be produced of high intensity and great fastness. Otherwise these dye-stufis, when diazotized on fiber, can be treated with a solution of sodium carbonate in water, by means of which very fast brown shades are produced.
In carrying out our process practically we proceed as followszAbout ten kilos, by weight, of unmordanted cotton are dyed by immersion for say one hour in a boiling solution prepared by dissolving 0.5 kilo, by weight, of the dye-stuff obtained from one molecular proportion of tetrazoortho diphenol-dimethylether and two molecular proportions of alpha naphthylamin beta monosulfo acid (Oleves beta acid) in two hundred and fifty kilos, by weight, of hot water and adding one kilo, by Weight, of common salt. Thereupon, the cotton, which is now dyed bluish-red, is washed carefully with cold water and then introduced in a solution of 0.3 kilo, by weight, of sodium nitrite in two hundred and fifty kilos, by weight, of cold water acidulated with 0.9 kilo, by weight, of hydrochloric acid (20 Baum). By well agitating the cotton in the acid bath the diazotizing is soon finished, after which the cotton is rinsed in cold water. By placing then the thus prepared cotton in an alkaline solution of 0.4 kilo, by weight, of the sod1um salt of beta naphthol the formation of the dye-stuff takes place on the fiber and the end of this reaction may easily be recognized 5 as the cotton gradually acquires a fast bluishblack color. When the intensity of the color no more increases, the cotton is carefully washed with water and dried.
Of course, the dye-stufi employed in the foregoing example can be replaced by analogous products from other tetrazo salts or from Oleves delta acid or by similar substantive dye-stuffs derived from the said Oleves acids (wlth the exception however of the dye-stuff from tetrazodiphenylchlorid and Oleves beta acid, which dye-stuff cannot be dyed owing to Its insolubility in water), and the above employed beta naphthol may be replaced by other suitable dye-stuff components (developers) shades being produced which in general are from violet to blue and black. The best shades, however, are obtained by employing beta-napbtol. The process herein before defined is of a great technical value 25 as the shades produced on the fiber in the aforesaid manner or in an analogous or similar way possess very great fastness to soaping and to the action of alkalies and acids.
When in the claim of this application we refer to beta naphthol we intend thereby to include as well the other described equivalents therefor.
Having now described our invention and in what manner the same is to be performed, what we claim as new, and desire to secure by Letters Patent, is-
The process of -dyeing cotton, which consists first, in dyeing in the well known manner cotton fiber or material by means of substantive dye stuffs containing Oleves acids, in subsequently diazotizing the dye stuffs fixed on the fiber, and finally combining the resulting diazo or tetrazo compounds likewise-on the fiber with beta naphthol.
CARL DUISBERG. PI-IILIPP OTT.
Witnesses:
THILO KROEBER, ROBERT DEMUTH.
It is hereby certified that in Letters Patent No. 523,809, granted July 31, 1894, upon the application of Carl Duisberg and Philipp Ott, of Elberfeld, Germany, for an improvement in Processes of Dyeing, an error appears in the printed specification requiring correction as follows: Page 1, line 30, the clause called Gleves alpha naphthylamin mono sulfo, should be stricken out and inserted after line 32 as now numbered, samev page; and that thesaid Letters Patent should be read with this correction therein that the same may conform to the record of the case in the Patent Oflice.
Signed, eountersigned, and sealed this 14th day of August, A. D1894.
J N O. M. REYNOLDS, Assistant Secretary of the Interior.
[sEAnj Oountersigned:
JOHN S. SEYMOUR,
Commissioner of Patents.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US523809A true US523809A (en) | 1894-07-31 |
Family
ID=2592604
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US523809D Expired - Lifetime US523809A (en) | Carl duisberg and philipp ott |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US523809A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040149767A1 (en) * | 2000-10-06 | 2004-08-05 | Boehm Michael G. | Web burster/inserter |
-
0
- US US523809D patent/US523809A/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040149767A1 (en) * | 2000-10-06 | 2004-08-05 | Boehm Michael G. | Web burster/inserter |
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