USRE11973E - Julius abel - Google Patents
Julius abel Download PDFInfo
- Publication number
- USRE11973E USRE11973E US RE11973 E USRE11973 E US RE11973E
- Authority
- US
- United States
- Prior art keywords
- abel
- julius
- acid
- matter
- blue
- Prior art date
Links
- 239000002253 acid Substances 0.000 description 18
- GRVFOGOEDUUMBP-UHFFFAOYSA-N Sodium sulfide Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 16
- 239000000243 solution Substances 0.000 description 14
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 12
- 239000011593 sulfur Substances 0.000 description 12
- 229910052717 sulfur Inorganic materials 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 229920000742 Cotton Polymers 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229960000583 Acetic Acid Drugs 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- 229940097275 Indigo Drugs 0.000 description 2
- 240000007871 Indigofera tinctoria Species 0.000 description 2
- 235000000177 Indigofera tinctoria Nutrition 0.000 description 2
- RSAZYXZUJROYKR-UHFFFAOYSA-N Indophenol Chemical compound C1=CC(O)=CC=C1N=C1C=CC(=O)C=C1 RSAZYXZUJROYKR-UHFFFAOYSA-N 0.000 description 2
- 235000011054 acetic acid Nutrition 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
- 239000007864 aqueous solution Substances 0.000 description 2
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- 239000000988 sulfur dye Substances 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
Definitions
- the coloring-matter so obtained contains sulfur and dyes unmordanted cotton in the presence of sodium sulfid blue shades. It can also be dyed from a vat in a manner similar to indigo. Various 2 5 beautiful shades of blue are obtained, which possess excellent fastness.
- My new coloring-matter is soluble in conce'ntrat-ed sulfuric acid with a pure-blue color and is also soluble in an aqueous solution of sodium sulfid, but is practically insoluble in pure water, hydrochloric acid, or dilute sodium-carbonatesolution.
- I a suitable quantity of a solution of sodium sulfid it first yields a blue solution.
- the parts are by weight.
- amido-indophenol-thiosnlfonic acid such as can be obtained from dimethyl-para-phenylene-diamin-thiosulfonic acid and phenol
- add them to a solution or mixture of one hundred and twenty (120) parts of sodium sulfid and twenty-five (25) parts of sulfur in fifty (50) parts of water. Raise the temperature gradually to about one hundred and twentyfive (125") degrees centigrade. Continue heating for ,sereral hours. The mass assumes the character of a dye-vat, and a test portion diluted with water on exposure to the airsay on filter-"paper-yields an intensely-blue coloring-matter.
- the greenish-colored filtrate contains the, new coloring-matter in the form of its leuco compound and can, if desired, be at once used for dyeing cotton,as cotton is dyed with sulfonic acids (such as can be obtained from 8;:
- dialkyl-para-phenylenediamin-thiosulfonic acids and phenol or its analogues are equivalent to the above-mentioned dimethyl amide indophenol thiosnlfonic acid for the purposes of my invention.
Description
UNITED STATES JULIUS ABEL, OF MANN HEIM, GERMANY, ASSIGNOR TO BADISCHE ANILIN &
SODA FABRIK, BADEN.
OF LUDXVIGSHAFEN, GERMANY, A CORPORATION OF BLUE SULFUR DYE AND PROCESS OF MAKING SAME.
- SPECIFICATION forming part of Reissued Letters Patent No. 11,973, dated March 4, 1902.
Original No. 679,199, dated July 23, 1901. Application for reissue filed February I, 1902. Serial No. 92,179-
To all u'lzom 7'1- may concern:
Be it known that I, JULIUS ABEL, doctor of philosophy and chemist, a citiz'en of the free Hausa town of Hamburg, residing at Mannheim, in the Grand Duchy of Baden,
Germany, have invented new and useful Improvements in Blue Coloring-Matter, of which the following is a specification.
If equimolecular proportions of a dialkylno para-phenylene-diamin 'thiosulfonic acid and a phenol be oxidized togethersay, for instance, with potassium biehromate in aceticacid solution-a dialkyl-amido-indopbenolthiosulfonic acid can be obtained. I have I5 discovered that new blue coloring-matter of great value can. be obtained by moderately heating such a dialkyl-amido-indophenolthiosulfonic acid for instance, dimethylamido=indophenol-thiosulfonic acid-with 2o sulfur and sodium snlfid. The coloring-matter so obtained contains sulfur and dyes unmordanted cotton in the presence of sodium sulfid blue shades. It can also be dyed from a vat in a manner similar to indigo. Various 2 5 beautiful shades of blue are obtained, which possess excellent fastness.
My new coloring-matter is soluble in conce'ntrat-ed sulfuric acid with a pure-blue color and is also soluble in an aqueous solution of sodium sulfid, but is practically insoluble in pure water, hydrochloric acid, or dilute sodium-carbonatesolution. On treatingit with I a suitable quantity of a solution of sodium sulfid it first yields a blue solution. On the addition of more sodium sulfid and heating scribed in the example: The parts are by weight.
amido-indophenol-thiosnlfonic acid (such as can be obtained from dimethyl-para-phenylene-diamin-thiosulfonic acid and phenol) and add them to a solution or mixture of one hundred and twenty (120) parts of sodium sulfid and twenty-five (25) parts of sulfur in fifty (50) parts of water. Raise the temperature gradually to about one hundred and twentyfive (125") degrees centigrade. Continue heating for ,sereral hours. The mass assumes the character of a dye-vat, and a test portion diluted with water on exposure to the airsay on filter-"paper-yields an intensely-blue coloring-matter. hen thispointisreached, dilute the entire-mixture with hot water and filter to separate from any insoluble impurity. The greenish-colored filtrate contains the, new coloring-matter in the form of its leuco compound and can, if desired, be at once used for dyeing cotton,as cotton is dyed with sulfonic acids (such as can be obtained from 8;:
the same or other dialkyl-para-phenylenediamin-thiosulfonic acids and phenol or its analogues) are equivalent to the above-mentioned dimethyl amide indophenol thiosnlfonic acid for the purposes of my invention.
Now what I claim is 1. .The process of producing new blue coloring-matter by treating dialkyl-amido-indophenol-thiosulfonic acid with sulfur and sodium sulfid, substantially as described.
2. The process of producing new blue coloring-matter bytreating dimethyl-amido-indophenol-thiosulfonicacid with sulfur and sodium sulfid, substantially as described.
3. The new blue coloring-matter containing 9 5 sulfur which is practically insoluble in pure water, hydrochloric acid or dilute carbonateof-soda solution, which on suitable reduction Example: Take fifty (50) partsof dimethyl- 5o c 1th sodiuni-sulfid solution is converted into my hand in the presence of two subscribing the form of leuco compound which is precipiwitnesses.
tated from its solution in sodium sulfid by hy- I drochloric acid and isvm'actieally insoluble in r JULIUS ABEL 5 carbonate-of-soda solution, substantially as Witnesses:
described. BERNHARD O. HESSE,
In testimony whereof I have hereunto set JACOB ADRIAN.
Family
ID=
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