US567567A - Albert herrmann - Google Patents
Albert herrmann Download PDFInfo
- Publication number
- US567567A US567567A US567567DA US567567A US 567567 A US567567 A US 567567A US 567567D A US567567D A US 567567DA US 567567 A US567567 A US 567567A
- Authority
- US
- United States
- Prior art keywords
- acid
- matter
- coloring
- leuco
- blue
- 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
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- LHYQAEFVHIZFLR-UHFFFAOYSA-L 4-(4-diazonio-3-methoxyphenyl)-2-methoxybenzenediazonium;dichloride Chemical compound [Cl-].[Cl-].C1=C([N+]#N)C(OC)=CC(C=2C=C(OC)C([N+]#N)=CC=2)=C1 LHYQAEFVHIZFLR-UHFFFAOYSA-L 0.000 description 3
- WDTRNCFZFQIWLM-UHFFFAOYSA-N 4-benzylaniline Chemical compound C1=CC(N)=CC=C1CC1=CC=CC=C1 WDTRNCFZFQIWLM-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000002932 luster Substances 0.000 description 2
- ISGXOWLMGOPVPB-UHFFFAOYSA-N n,n-dibenzylaniline Chemical compound C=1C=CC=CC=1CN(C=1C=CC=CC=1)CC1=CC=CC=C1 ISGXOWLMGOPVPB-UHFFFAOYSA-N 0.000 description 2
- QFRIIGBAHKSVIU-UHFFFAOYSA-N n-benzyl-2-methylaniline Chemical compound CC1=CC=CC=C1NCC1=CC=CC=C1 QFRIIGBAHKSVIU-UHFFFAOYSA-N 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000010446 mirabilite Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 210000002268 wool Anatomy 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
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
- C09B11/10—Amino derivatives of triarylmethanes
Definitions
- This coloring-matter consists of the sulfonic acids of InetaoXydibenzyldiamidotriphenylcarbinol,
- this coloring-matter is carried out in a manner analogous to the process described in Reissued Letters Patent granted to me on May 20, 1890, No. 11,077, Where in place of the bases mentioned those indicated by the above formulae are used.
- the symmetrical metaamidodibenzyldiamidotriphenylmethane 0r symmetrical metaamidodibenzyldiamidodi0rthotolylphenylmethane or metaamidotetrabenzyldiamidotriphenylmethane are converted into the corresponding metaoxyleuco bases by means of nitrous acid, or the metaoxyleuco bases are obtained by condensation of monobenzylanilin, monobenzylorthotoluidin, or dibenzylanilin with metaoxybcnzaldehyde.
- the resulting metaoxyleuco bases are then sulfonated by co11- 6o centrated or fuming sulfuric acid and the leu
- the sulfonic acid of monobenzylanilin or 1nonobenzylorthotoluidin or dibenzylanilin may be condensed with metaoxybenzaldehyde and the resulting leuco-sulfonic acids then further sulfonated to the leuco-sulfonic acids of the blue c0loring matters, and these oxidized to the color ing-matters.
- the new coloring-matter is a copper-red powder with metallic luster. It dissolves in water with a blue color, is Very slightly soluble in alcohol, almost insoluble in benzene and ether. The aqueous solution becomes green -on addition of a mineral acid. Ammonia and metaoxybenzaldehyde, sulfonating the metaoxyleuco bases obtained thereby, and then oxidizing the resulting leuco-sulfonic acid, substantially as set forth.
- a fast-blue coloringmatter being a copper-red powder with metallic luster, soluble in water, scarcely soluble in alcohol, insoluble in ether and benzene, dyeing wool and silk in an acid bath blue tints, the aqueous solution turning green with mineral acid and red on heating with caustic soda, substantially as set forth.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
UNITED STATES ATENT FFlCE.
BLUE COLORING-MATTER.
SPECIFICATION formingpart of Letters Patent No. 567,567, dated september 8, 1896.
Application filed January 11,1895. Serial No. 534,586. ($peoimens.) Patented in Germany June 6, 1893, No. 745,014,- in France July 31, 1893,110- 192,8 07,a11(1i11 England July 81, 1893,N0.14,671.
To all whom it may concern:
Be it known that I, ALBERT HERRMANN, a citizen of the Empire of Germany, and a resident of I-ldchst-on-the-lVIain, in the Empire of Germany, have invented certain new and useful Improvements in the Production of Green-Blue Coloring-Matter, (for which Letters Patent Were granted to me in Germany, No. 71,014, dated June 6, 1893; in France, by Certificate of Addition to Letters Patent No.192,807, dated July 31, 1893, and in Great Britain, No. 11,671, dated July 31, 1803,) of which the following is a specification.
I have discovered a method for manufacturing a fast blue acid coloring matter. This coloring-matter consists of the sulfonic acids of InetaoXydibenzyldiamidotriphenylcarbinol,
or metaoxydibenzyldiamidodiotolylphenylcarbinol,
C 11 OH (meta) C,H IIOC e s( 3) or metaoxytetrabenzyldiamidotriphenylcarbinol,
The manufacture of this coloring-matter is carried out in a manner analogous to the process described in Reissued Letters Patent granted to me on May 20, 1890, No. 11,077, Where in place of the bases mentioned those indicated by the above formulae are used. Thus in accordance with said process the symmetrical metaamidodibenzyldiamidotriphenylmethane 0r symmetrical metaamidodibenzyldiamidodi0rthotolylphenylmethane or metaamidotetrabenzyldiamidotriphenylmethane are converted into the corresponding metaoxyleuco bases by means of nitrous acid, or the metaoxyleuco bases are obtained by condensation of monobenzylanilin, monobenzylorthotoluidin, or dibenzylanilin with metaoxybcnzaldehyde. The resulting metaoxyleuco bases are then sulfonated by co11- 6o centrated or fuming sulfuric acid and the leuco-sulfonic acid oxidized by peroxid of lead or similar agents.
Instead of the bases the sulfonic acid of monobenzylanilin or 1nonobenzylorthotoluidin or dibenzylanilin may be condensed with metaoxybenzaldehyde and the resulting leuco-sulfonic acids then further sulfonated to the leuco-sulfonic acids of the blue c0loring matters, and these oxidized to the color ing-matters.
Example: 30.4 parts, by Weight, of monobenzylorthotoluidin are dissolved in two hundred parts, by Weight, of alcohol. To this so lution twenty-two parts, by Weight, of thirty- 7 one per cent. hydrochloric acid and 12.2 parts, by weight, of metaoxybenzaldehyde are added. This solution is boiled for tWenty-. four hours in an inverted condenser and then the alcohol is distilled off. The residual leuco base is boiled with much water with addition of dilute sulfuric acid, then treated With boiling water until it reacts neutral, and finally dried on a water-bath. The sulfonation is effected by treating this leuco base with sulfurie acid, monohydrated sulfuric acid, or fuming sulfuric acid. It has proved most advantageous to dissolve the leuco base in five parts, by Weight, of monohydrated sulfuric acid. The product of the reaction is poured into Water and the precipitated leuco sulfonic acid filtered off and converted into the calcium or sodium salt. This is then treated with the calculated quantity of peroxid of lead and of a mineral acid or acetic acid. The lead is 5 precipitated from the resulting blue solution with Glauber salt. In the filtrate the coloring-matter is precipitated with salt. The solution of the coloring-matter may also be evaporated to dryness.
The new coloring-matter is a copper-red powder with metallic luster. It dissolves in water with a blue color, is Very slightly soluble in alcohol, almost insoluble in benzene and ether. The aqueous solution becomes green -on addition of a mineral acid. Ammonia and metaoxybenzaldehyde, sulfonating the metaoxyleuco bases obtained thereby, and then oxidizing the resulting leuco-sulfonic acid, substantially as set forth.
2. The process of producing fast-blue coloring-matter, which consists in condensing the sulfonic acids of monobenzylanilin or its homologues with metaoxybenzaldehyde, then again sulfonatin g the resulting leuco-sulfonic acids whereby leuco-sulfonic acids of the blue coloring-matter are produced, and oxidizing the latter to the coloring-matter with a suitable reagent such as lead peroxid,'substantially as set forth.
3. As a new product, a fast-blue coloringmatter being a copper-red powder with metallic luster, soluble in water, scarcely soluble in alcohol, insoluble in ether and benzene, dyeing wool and silk in an acid bath blue tints, the aqueous solution turning green with mineral acid and red on heating with caustic soda, substantially as set forth.
In testimony that I claim the foregoing as my invention I have signed my name in presence of two subscribing witnesses.
ALBERT HERRMANN.
WVitnesses:
HEINRICH HAHN, BERNHARD LEYDECKER.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US567567A true US567567A (en) | 1896-09-08 |
Family
ID=2636274
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US567567D Expired - Lifetime US567567A (en) | Albert herrmann |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US567567A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2904433A (en) * | 1950-05-12 | 1959-09-15 | Agfa Ag | Process of producing antihalation and filter layers |
-
0
- US US567567D patent/US567567A/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2904433A (en) * | 1950-05-12 | 1959-09-15 | Agfa Ag | Process of producing antihalation and filter layers |
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