US412615A - Albert herrmann - Google Patents
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- US412615A US412615A US412615DA US412615A US 412615 A US412615 A US 412615A US 412615D A US412615D A US 412615DA US 412615 A US412615 A US 412615A
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- US
- United States
- Prior art keywords
- methane
- carbinol
- weight
- metaethoxy
- metamethoxy
- Prior art date
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- Expired - Lifetime
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- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 34
- 239000002585 base Substances 0.000 description 32
- 239000002253 acid Substances 0.000 description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 22
- 159000000007 calcium salts Chemical class 0.000 description 20
- 150000007513 acids Chemical class 0.000 description 18
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 239000001117 sulphuric acid Substances 0.000 description 16
- 235000011149 sulphuric acid Nutrition 0.000 description 16
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 14
- 238000009835 boiling Methods 0.000 description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- 229910052500 inorganic mineral Inorganic materials 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 10
- 239000011707 mineral Substances 0.000 description 10
- 235000010755 mineral Nutrition 0.000 description 10
- 235000011121 sodium hydroxide Nutrition 0.000 description 10
- 125000005998 bromoethyl group Chemical group 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N Diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 4
- JLTDJTHDQAWBAV-UHFFFAOYSA-N Dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 4
- JDEJGVSZUIJWBM-UHFFFAOYSA-N N,N,2-trimethylaniline Chemical compound CN(C)C1=CC=CC=C1C JDEJGVSZUIJWBM-UHFFFAOYSA-N 0.000 description 4
- YQYUUNRAPYPAPC-UHFFFAOYSA-N N,N-diethyl-2-methylaniline Chemical compound CCN(CC)C1=CC=CC=C1C YQYUUNRAPYPAPC-UHFFFAOYSA-N 0.000 description 4
- HSZCJVZRHXPCIA-UHFFFAOYSA-N N-benzyl-N-ethylaniline Chemical compound C=1C=CC=CC=1N(CC)CC1=CC=CC=C1 HSZCJVZRHXPCIA-UHFFFAOYSA-N 0.000 description 4
- LXZGVFCKZRHKMU-UHFFFAOYSA-N N-benzyl-N-methylaniline Chemical compound C=1C=CC=CC=1N(C)CC1=CC=CC=C1 LXZGVFCKZRHKMU-UHFFFAOYSA-N 0.000 description 4
- PPHQUIPUBYPZLD-UHFFFAOYSA-N N-ethyl-N-methylaniline Chemical compound CCN(C)C1=CC=CC=C1 PPHQUIPUBYPZLD-UHFFFAOYSA-N 0.000 description 4
- ITMSSZATZARZCA-UHFFFAOYSA-N N-ethyl-N-phenylaniline Chemical compound C=1C=CC=CC=1N(CC)C1=CC=CC=C1 ITMSSZATZARZCA-UHFFFAOYSA-N 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 230000000875 corresponding Effects 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 239000002932 luster Substances 0.000 description 4
- 150000005217 methyl ethers Chemical group 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- 229940097275 Indigo Drugs 0.000 description 2
- 240000007871 Indigofera tinctoria Species 0.000 description 2
- 235000000177 Indigofera tinctoria Nutrition 0.000 description 2
- 244000278455 Morus laevigata Species 0.000 description 2
- 235000013382 Morus laevigata Nutrition 0.000 description 2
- DYFFAVRFJWYYQO-UHFFFAOYSA-N N-methyl-N-phenylaniline Chemical compound C=1C=CC=CC=1N(C)C1=CC=CC=C1 DYFFAVRFJWYYQO-UHFFFAOYSA-N 0.000 description 2
- AAAQKTZKLRYKHR-UHFFFAOYSA-N Triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 2
- LZTRCELOJRDYMQ-UHFFFAOYSA-N Triphenylmethanol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(O)C1=CC=CC=C1 LZTRCELOJRDYMQ-UHFFFAOYSA-N 0.000 description 2
- 210000002268 Wool Anatomy 0.000 description 2
- 150000005215 alkyl ethers Chemical class 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- MCOQHIWZJUDQIC-UHFFFAOYSA-N barban Chemical compound ClCC#CCOC(=O)NC1=CC=CC(Cl)=C1 MCOQHIWZJUDQIC-UHFFFAOYSA-N 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- AOJDZKCUAATBGE-UHFFFAOYSA-N bromomethane Chemical group Br[CH2] AOJDZKCUAATBGE-UHFFFAOYSA-N 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N epichlorohydrin Chemical group ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- -1 iodo ethyl Chemical group 0.000 description 2
- KPJPHPFMCOKUMW-UHFFFAOYSA-N iodomethane Chemical group I[CH2] KPJPHPFMCOKUMW-UHFFFAOYSA-N 0.000 description 2
- VFCNQNZNPKRXIT-UHFFFAOYSA-N malachite green cation Chemical class C1=CC(N(C)C)=CC=C1C(C=1C=CC=CC=1)=C1C=CC(=[N+](C)C)C=C1 VFCNQNZNPKRXIT-UHFFFAOYSA-N 0.000 description 2
- 150000004682 monohydrates Chemical class 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M superoxide Chemical class [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 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
- 238000005406 washing Methods 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
- 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
- C09B11/12—Amino derivatives of triarylmethanes without any OH group bound to an aryl nucleus
- C09B11/14—Preparation from aromatic aldehydes, aromatic carboxylic acids or derivatives thereof and aromatic amines
Definitions
- My invention relates to the production of coloring-matters obtained from the etherized compounds of metaoxytetralkyldiamidotri phenyl methane or, rather, from metamethoxy or metaethoxy tetralkyl diamido triphenyl carbinol.
- the sulphonic acid of these compounds dyes greenblue tints which are very fast.
- the ether compounds obtained by the process just described may also be produced by methylizing or ethylizing of the metaoxytetralkyldiamido triphenyl methane. These oxy leuco bases are to this elfect heated for several days in a close vessel in a Water-bath with three or four times their quantity of alcohol,caustic soda, (one molecule,) and an excess of chloro, bromo, or iodo methyl or chloro, bromo,or iodo ethyl.
- thirty parts, by weight, of metaoxytetraethyldiamr dotriphenyl methane twenty parts, by weight,
- Example N0 1.Thirty parts, by weight, of metamethoxytetraethyldiamidotriphenyl methane are dissolved in one hundred and fifty parts, by weight, of fuming sulphuric acid of ten percent. S0 and the solution left standing at ordinary temperature until a sample gives with diluted ammonia a clear solution. Now the product of the reaction is poured into water and the solution converted into the calcium salt in well-known manner. The calcium salt is a powder very easily soluble in alcohol and in water.
- Example N0 2.-Somewhat different is the process for the preparation of the sulphonic acids of those leuco bases which in the amido group still contain aromatic residues, (capable of being sulphonated,) such as benzyl or phenyl.
- the sulphonic acid of the methoxidized and ethoxidized leuco bases can also be produced by treatment of the calcium or sodium salts of the metaoxytetralkyldiamidotriphenyl-methane sulphonic acids with methyl or ethyl halogenides.
- EmampZa-Thirty parts, by weight, of the calcium salt of metaoxytetraethyldiamidotriphenyl methane, twenty parts, by weight, of bromoethyl, and one hundred parts, by weight, of alcohol in a vessel in a water bath are heated to boiling-point for twenty to twenty-f0 or hours.
- the excess of bromo-ethyl and the alcohol are distilled off.
- To the remaining (aqueous) solution is added a small quantity of diluted sulphuric acid, and the whole is left at rest for several days,when the greatest part of the leuco sulphonic acid of the ethoxidized base will have crystallized out. This is pressed off and converted into the calcium salt.
- the calcium salts of the leuco sulphonic acids hereinbefore mentioned are converted into coloring-matter by oxidation with superoxides in presence of the calculated quantity of a mineral acid.
- a mineral acid For example, ten parts, by weight, of the calcium salt of the sulphonic acid prepared from metamethoxytetraethyldiamidotriphenyl methane are dissolved in The so-- IIO about three hundred parts, by Weight, of water. Then there are added the calculated quantities of diluted sulphuric acid and peroxide of lead filtered off from the precipitated sulphate of lead, and the blue solution of the coloring-matter is evaporated to dryness.
- the new coloring-matter is a copper-red powder of metallic luster, dissolving quite easily in water, giving blue color.
- the aqueous so1ut-ion turns green on the addition of an excess of mineral acid.
- the blue color of the aque-v ous solution does not disappear on the addition of soda-lye when cold, not even when it is boiled with a solution of ammonia or soda, and it turns violet only when it is boiled with soda-lye.
- Metamethoxy and metaethoxy tetralkyldiamidotriphenyl carbinol may be converted in green-blue coloring-matter identical with the coloring-matter described in sub. III by treatment with sulphuric acid or fuming sulphuric acid.
- EmampZa-Ten parts, by weight, of metamethoxytetraethyldiamidotriphenyl carbinol are dissolved in one hundred parts, by weight,
Description
' UNITED STATES PATENT OFFICE.
ALBERT HERRMANN, OF HOCHST-ON-THE-MAIN, GERMANY, ASSIGNOR TO THE FARBWERKE, VORMALS MEISTER, LUCIUS & BRUNING, OF SAME PLACE.
' WCOIIORING-MATTER.
SPECIFICATION forming part of Letters Patent No. 412,615, dated October 8, 1889.
Application filed January 15, 1889. Serial No. 296,391. (Specimens) Patented in Germany August 18, 1888; in Belgium September 3, 1888, No. 83,115 i in France September 5. 1888, No. 192,807, and in Italy September 30, 1888, XLVII, 176.
To all whom it may concern..-
Be it known that I, ALBERT HERRMANN, doctor of philosophy, a citizen of the Empire of Germany, residing at Hochst-on-the-Maine, in the Empire of Germany, have invented certain new and useful Improvements in Coloring-Matter, (patented in Germany August 18, 1888, F. 3,757; in Belgium September 3, 1888, No. 83,115; in France September 5, 1888, No. 192,807, and in Italy Vol. 47, No. 176, September 30, 1888;) 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.
My invention relates to the production of coloring-matters obtained from the etherized compounds of metaoxytetralkyldiamidotri phenyl methane or, rather, from metamethoxy or metaethoxy tetralkyl diamido triphenyl carbinol. The sulphonic acid of these compounds dyes greenblue tints which are very fast.
In carrying out my invention I proceed as follows:
I. PRODUCTION OF THE ALKYL ETHERS OF M E TAO XY T E TRALKYLDIAMIDOTRIPHE NYL METI-IANE.
A. The methyl and ethylethers of the leuco bases O H OAlk (meta) O 4 e 4 2)2 rnethoxybenzaldehyde three to twenty-four hours to 130 centigrade. The product of the reaction is supersaturated with alkali and heated by a current of steam, and the remaining leuco base is boiled and finally dried. In a similar manner is obtained the ethoxidized leuco base by means of metaethoxybenzalde- .hyde
/OO H xcnofif,
which forms at the boiling-point, which is about 245 centigrade, a colorless fluid. For the production of the corresponding leuco bases are used, in the place of the diethylaniline in the same process, dimethylaniline, methylethylaniline, methylbenzylaniline, ethylbenzylaniline, dimethyl-orthotoluidine, diethyl orthotoluidine, methyl diphenylamine, or ethyldiphenylamine.
B. The ether compounds obtained by the process just described may also be produced by methylizing or ethylizing of the metaoxytetralkyldiamido triphenyl methane. These oxy leuco bases are to this elfect heated for several days in a close vessel in a Water-bath with three or four times their quantity of alcohol,caustic soda, (one molecule,) and an excess of chloro, bromo, or iodo methyl or chloro, bromo,or iodo ethyl. Thus, for example, thirty parts, by weight, of metaoxytetraethyldiamr dotriphenyl methane, twenty parts, by weight,
of bromo-ethyl, one hundred parts, by weight,
of alcohol, and the calculated quantity of canstic soda are heated in a vessel in a water bath for forty-eight hours. Afterward the alcohol and the excess of bromo-ethyl are distilled OE, and the residue is boiled with water and dried. The me'tamethoxidized and ethoxidized tetralkyldiamidotriphenyl methanes are, when hot, semiliquid. When cold they are brittle, pulverizable resinous bodies which show but little inclination to crystallize, andin consequence of these qualities it is rather difficult to obtain them in a perfectly pure state. *The one relatively most easy to be obtained in small colorless crystals is the metaethoxydiethyldibenzyldiamidotriphenyl methane. The bases dissolve readily in ether, benzol, and toluolles's readily in alcohol. 'Ag'ainst diluted mineral acids they behave in the same way as the corresponding non-alkylized bases. Those bases deriving from dimethylaniline, diethylaniline, ethylmethylaniline, dimethyl-orthotoluidine, and diethyl-orthotoluidine are relatively stronger bases, which dissolve readily in diluted mineral acids, whereas the bases deriving from methyl and ethyl benzylaniline and from methyl and ethyl diphenylamine show scarcely any basic qualities.
II.PRODUCTION OF sULPHoNIc ACID OF THE METHOXIDIZED AND ETHOXIDIZED LEUCO BASES.
A. The metamethoxydized andmetaethoxidized leuco bases of the generic formula.
/C PLOAlk(meta) s H4NA1k can be converted into the sulphonic acid by heating them with concentrated sulphuric acid; but, principallyin consideration of the purity of the product to be obtained, it is more advantageous to use fuming sulphuric acid instead of the ordinary acid. The process is as follows:
Example N0. 1.Thirty parts, by weight, of metamethoxytetraethyldiamidotriphenyl methane are dissolved in one hundred and fifty parts, by weight, of fuming sulphuric acid of ten percent. S0 and the solution left standing at ordinary temperature until a sample gives with diluted ammonia a clear solution. Now the product of the reaction is poured into water and the solution converted into the calcium salt in well-known manner. The calcium salt is a powder very easily soluble in alcohol and in water. In the same manner is carried out the production of the sulphonic acids respectively of their calcium salts of metaethoxytetraethyldiamidotriphenyl' methane, metamethoxy and metaethoxy tetramethyldiamidotriphenyl methane, metamethoxy and metaethoxydimethyldiethyldiamidotriphenyl methane symmetric, metamethoxy and metaethoxy dimethyldiet-hyldiamidotriphenyl methane unsymmetric-,1netamethoxy and metaethoxy tetramethyldiorthotolylphenyl methane, metamethoxy and metaethoxy tetraethyldiorthotolylph en'yl methane.
Example N0. 2.-Somewhat different is the process for the preparation of the sulphonic acids of those leuco bases which in the amido group still contain aromatic residues, (capable of being sulphonated,) such as benzyl or phenyl. The compounds belonging to this class are the following: metamethoxy and metaethoxy dibenzyldiethyld ia midotriphenyl methane, metamethoxy and metaethoxy di= benzyldimethyldiamidotriphenyl methane, metamethoxy and metaethoxy diphenyldiethyldiamidotriphenyl methane, metametlr oxy and metaethoxy diphenyldimethyldiamidotriphenyl methane.
In the following example is described the way in which is carried out the sulphonation of these leuco bases: Thirty parts, by weight,
of metamethoxydibenzyldiethyldiamidotrt phenyl methane are dissolved in one hundred and iiftyparts, by weight, of fuming sulphuric acid of twenty per cent. 80,. At ordinary temperature is formed a sulphonic acid scarcely soluble in water. Then the solution is heated for several hours to about centigrade, until a sample dissolves easily in water with blue coloring and gives with diluted ammonia a pure blue solution having the shade of a diluted ammoniacal solution of oxide of copper. N ow the product of the reaction is poured into water and converted into the calcium salt in manner well known. dium and calcium salts are crystalline bodies colorless in pure state and readily soluble in water and alcohol.
B. The sulphonic acid of the methoxidized and ethoxidized leuco bases can also be produced by treatment of the calcium or sodium salts of the metaoxytetralkyldiamidotriphenyl-methane sulphonic acids with methyl or ethyl halogenides.
EmampZa-Thirty parts, by weight, of the calcium salt of metaoxytetraethyldiamidotriphenyl methane, twenty parts, by weight, of bromoethyl, and one hundred parts, by weight, of alcohol in a vessel in a water bath are heated to boiling-point for twenty to twenty-f0 or hours. The excess of bromo-ethyl and the alcohol are distilled off. To the remaining (aqueous) solution is added a small quantity of diluted sulphuric acid, and the whole is left at rest for several days,when the greatest part of the leuco sulphonic acid of the ethoxidized base will have crystallized out. This is pressed off and converted into the calcium salt.
III. OXIDATION OF THE METAMETHOXIDIZED AND METAETHOXIDIZED LEUCO SULPHONIC ACIDS OF THE MALACHITE GREEN SERIES.
The calcium salts of the leuco sulphonic acids hereinbefore mentioned are converted into coloring-matter by oxidation with superoxides in presence of the calculated quantity of a mineral acid. For example, ten parts, by weight, of the calcium salt of the sulphonic acid prepared from metamethoxytetraethyldiamidotriphenyl methane are dissolved in The so-- IIO about three hundred parts, by Weight, of water. Then there are added the calculated quantities of diluted sulphuric acid and peroxide of lead filtered off from the precipitated sulphate of lead, and the blue solution of the coloring-matter is evaporated to dryness. The new coloring-matter is a copper-red powder of metallic luster, dissolving quite easily in water, giving blue color. The aqueous so1ut-ion turns green on the addition of an excess of mineral acid. The blue color of the aque-v ous solution does not disappear on the addition of soda-lye when cold, not even when it is boiled with a solution of ammonia or soda, and it turns violet only when it is boiled with soda-lye. This characteristic quality of the new coloring-mat-ter-namely, the great resistance to'the action of alkaliesis of great advantage for technical purposes and consti tutes a great merit of the invention. These compounds dye wool and silk in an acid bath green-blue, and excel in dyeing a level tint, in which respect the sulphonic acids of indigo are equaled. In consequence of the resistance to alkalies the tints produced are (compared to those produced with indigo-carmiue) very fast in washing.
IV. SULPHONATION OF METAMETHOXY AND METAETHOXY TETRALKYLDIAMIDOTRIPHE- NYL CARBINOL.
Metamethoxy and metaethoxy tetralkyldiamidotriphenyl carbinol may be converted in green-blue coloring-matter identical with the coloring-matter described in sub. III by treatment with sulphuric acid or fuming sulphuric acid.
EmampZa-Ten parts, by weight, of metamethoxytetraethyldiamidotriphenyl carbinol are dissolved in one hundred parts, by weight,
' of monohydrate and the solution heated to 50 In quite the same manner analogous coloring-matter is obtained from the methyl and ethyl ethers of metaoxytetramethyldiamidotriphenyl carbinol, metaoxytetraethyldiamidotriphenyl carbin 01, metaoxydimethyldiethyldiamidotriphenyl carbinol symmetric, metaoxydimethyldiethyldiamidotriphenyl carbinol unsymmetric, metaoxytetramethyldiamidodiorthotolylphenyl carbinol, metaoxytetraethyldiamidodiorthotolylphenyl carbinol, metaoxydimethyldibenzyldiamidotrip h e nyl carbinol, metaoxydiethyldibenzyldiamidotriphenyl carbinol, metaoxydimethyldiphenyldiamidotriphenyl carbinol, and metaoxydiethyldiphenyldiamidotriphenyl carbinol.
What I claim as new, and wish to secure by Letters Patent, is-
The new fast green-blue coloring-matter obtained, as described, from the etherized compounds of metaoxytetralkyldiamidotriphenyl methane or metamethoxy or metaethoxy tetralkyldiamidotriphenyl carbinol in the form of a copper-red powder of metallic luster, easily soluble in water, and giving,when so dissolved, a blue color which remains when soda-lye is added or when boiled with a solution of ammonia or soda, changes to violet only when boiled with soda-lye, and turns green on the addition of mineral acids, as set forth.
In testimony whereof I affix my signature in presence of two witnesses.
ALBERT HERRMANN.
Witnesses:
J OSEF REVERDY, HEINRICH HAHN.
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US412615A true US412615A (en) | 1889-10-08 |
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US412615D Expired - Lifetime US412615A (en) | Albert herrmann |
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5194390A (en) * | 1988-07-05 | 1993-03-16 | Miles Inc. | Composition for the assay of albumin |
US20020179131A1 (en) * | 2001-06-01 | 2002-12-05 | The Regents Of The University Of Minnesota | Tray apparatus and methods regarding same |
-
0
- US US412615D patent/US412615A/en not_active Expired - Lifetime
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5194390A (en) * | 1988-07-05 | 1993-03-16 | Miles Inc. | Composition for the assay of albumin |
US20020179131A1 (en) * | 2001-06-01 | 2002-12-05 | The Regents Of The University Of Minnesota | Tray apparatus and methods regarding same |
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