US521095A - Heinrich august bernthsen - Google Patents
Heinrich august bernthsen Download PDFInfo
- Publication number
- US521095A US521095A US521095DA US521095A US 521095 A US521095 A US 521095A US 521095D A US521095D A US 521095DA US 521095 A US521095 A US 521095A
- Authority
- US
- United States
- Prior art keywords
- new
- parts
- heinrich
- bernthsen
- dye
- 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
- 239000000975 dye Substances 0.000 description 14
- 238000004519 manufacturing process Methods 0.000 description 8
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000000835 fiber Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N Resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- MCTQNEBFZMBRSQ-UHFFFAOYSA-N (3-amino-4-phenyldiazenylphenyl)azanium;chloride Chemical compound Cl.NC1=CC(N)=CC=C1N=NC1=CC=CC=C1 MCTQNEBFZMBRSQ-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 239000001045 blue dye Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000003518 caustics Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000004780 naphthols Chemical class 0.000 description 2
- 230000001264 neutralization Effects 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-N nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 235000002639 sodium chloride Nutrition 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 235000013311 vegetables Nutrition 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
- C09B35/02—Disazo dyes
- C09B35/039—Disazo dyes characterised by the tetrazo component
- C09B35/08—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl
Definitions
- Our invention relates to the manufacture of a new blue dye which fixes itself on cotton goods and the like from a boiling neutral or alkaline bath without the aid of a mordant.
- Our new dye is a mixed or unsymmetrical disazo-dyestuff and is derived from a new amido-naphthol-sulfoacid which we have invented and which is obtained by melting with a caustic alkali the 2--4t'--2 naphthylamine-disulfoacid (Armstrong and Wynne, Proceedings of the Chemical Society, 1890, page 128) at a temperature of about 170 to 195 centigrade as more fully described in the French Patent No. 227,892, of February 13, 1893.
- This new acid has the constitution represented by the formulaz'
- the new dye is obtained by first preparing a so-called intermediate product by combining one molecular proportion thereof with one molecular proportion of tetrazo-ditolyl in alkaline solution and then further combining this intermediate product with one molecular proportion of 1.4-naphthol-monosulfoacid.
- our new dye possesses a high technical value on account of its great affinity for vegetable fiber and the fastness of the coloratiohs which it yields. These are a reddish shade of blue and resist well the action of acids and alkalies and of light. Further we have discovered that our new dye can be diazotized on the fiber by treating the goods dyed with it with nitrous acid and that the resulting compound will then combine with other dyestufE-components hereinafter mentioned yielding various very fast shades of color.
- the components which we recommend for use in this way are for instance the naphthols, resorcinol, meta-phenylene-diamin, meta-toluylene-diamin,ethyLbeta-naphthylamin, alpha-amido-beta-naphthol-ether, para-amido-diphenylamin, and chrysoidin.
- the new coloring-matter which can be derived from tetrazo-ditolyl, the 2.4 .flamido-naphtholsulfoacid and 1.4-naphthol-sulfoacid and in the form of soda salt possesses the constitu- 0 tion represented by the formula:
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
UNITED STATES AENT Futon..-
HEINRICH AUGUST BERNTHSEN, OF MANNHEIM, AND PAUL JULIUS, OF LUDWIGSHAFEN, ASSIGNORS TO THE BAD'ISCHE ANILIN AND SODA FABRIK, OF LUDWIGSHAFEN, GERMANY.
SUBSTANTIVE BLUE DYE.
SPECIFICATION. forming part of Letters Patent No. 521,095, dated June 5', 1894.
Application filed March 30, 1894:. Serial No. 505,739- (Specimenal' Patented in England February 6, 1893, No. 2,614, and in France May 15, 1893.110. 227,892.
To all whom it may concern:
Be it known that we, HEINRICH AUGUST BERNTHSEN, a subject of the King of Prussia, residing at Mannheim, in the Grand Duchy of Baden, and PAUL JULIUS, a subject of the Emperor ofAustria-Hungary, residing at Ludwigshafen, in the Kingdom of Bavaria, Empire of Germany, have invented new and useful Improvements in the Manufacture of new Substantive Blue Dye, (forwhich patents have been obtained in England, No. 2,614, dated February 6, 1893, and in France, No. 227,892, oated May 15, 1893,) of which the following is a specification.
Our invention relates to the manufacture of a new blue dye which fixes itself on cotton goods and the like from a boiling neutral or alkaline bath without the aid of a mordant.
Our new dye is a mixed or unsymmetrical disazo-dyestuff and is derived from a new amido-naphthol-sulfoacid which we have invented and which is obtained by melting with a caustic alkali the 2--4t'--2 naphthylamine-disulfoacid (Armstrong and Wynne, Proceedings of the Chemical Society, 1890, page 128) at a temperature of about 170 to 195 centigrade as more fully described in the French Patent No. 227,892, of February 13, 1893. This new acid has the constitution represented by the formulaz' The new dye is obtained by first preparing a so-called intermediate product by combining one molecular proportion thereof with one molecular proportion of tetrazo-ditolyl in alkaline solution and then further combining this intermediate product with one molecular proportion of 1.4-naphthol-monosulfoacid.
Our new dye possesses a high technical value on account of its great affinity for vegetable fiber and the fastness of the coloratiohs which it yields. These are a reddish shade of blue and resist well the action of acids and alkalies and of light. Further we have discovered that our new dye can be diazotized on the fiber by treating the goods dyed with it with nitrous acid and that the resulting compound will then combine with other dyestufE-components hereinafter mentioned yielding various very fast shades of color. The components which we recommend for use in this way are for instance the naphthols, resorcinol, meta-phenylene-diamin, meta-toluylene-diamin,ethyLbeta-naphthylamin, alpha-amido-beta-naphthol-ether, para-amido-diphenylamin, and chrysoidin.
The following example will serve to illus trate the manner in which-our invention can be carried into practical effect and our new dye obtained. The parts are by weight.
Example: Prepare a tetrazo-ditolyl-lsolution in the usual way from about twenty one and one fifth parts of tolidin, fifteen hundred parts of water, 'fifty eight parts of hydrochloric acid (containing about thirty per cent. real acid H01) and fourteen parts of sodium nitrite in ten per cent. solution, Pour this tetrazo-solution into .an ice cold dilute soda solution containing about fifty parts of calcined soda and then immediately add a solution of about twenty four parts of the new amido-naphthol-sulfoacid in six hundred parts of water and twenty one parts of calcined soda. When the production of the intermediate compound in the form of a brown black precipitate is complete, which takes but a short time, adda solution of twenty five parts of l.4=-naphthol-sulfonate of soda and stir for twelve hours or longer. Finally boil the mixture, precipitate the dye with common salt, filter, press and dry.
en SO Nat l) Now what we claim as new, and desire to secure by Letters Patent, is
As a new article of manufacture the new coloring-matter which can be derived from tetrazo-ditolyl, the 2.4 .flamido-naphtholsulfoacid and 1.4-naphthol-sulfoacid and in the form of soda salt possesses the constitu- 0 tion represented by the formula:
and which is readily soluble in hot and cold water giving red violet solutions, slightly soluble in alcohol, practically insoluble in benzene, ether and ligroin,soluble in sulfuric acid giving a beautiful blue solution and which on diazotizing 0n the fiber assumes a blue color, all substantially as hereinbefore described.
In testimony whereof We have hereunto set our hands in the presence of two subscribing witnesses.
HEINRICH AUGllS'l llEltNIllSIll. PAUL JULIUS.
Witnesses:
ERNEST F. EI-IRHARDT, ADOLPH REUTLINGER.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US521095A true US521095A (en) | 1894-06-05 |
Family
ID=2589893
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US521095D Expired - Lifetime US521095A (en) | Heinrich august bernthsen |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US521095A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2762794A (en) * | 1953-06-10 | 1956-09-11 | Geigy Ag J R | Metallisable polyazo dyestuffs |
| US4008215A (en) * | 1973-10-12 | 1977-02-15 | Bayer Aktiengesellschaft | Sulfonic-acid substituted disazo dyestuffs |
-
0
- US US521095D patent/US521095A/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2762794A (en) * | 1953-06-10 | 1956-09-11 | Geigy Ag J R | Metallisable polyazo dyestuffs |
| US4008215A (en) * | 1973-10-12 | 1977-02-15 | Bayer Aktiengesellschaft | Sulfonic-acid substituted disazo dyestuffs |
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