US471638A - Benno homolka - Google Patents

Benno homolka Download PDF

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US471638A
US471638A US471638DA US471638A US 471638 A US471638 A US 471638A US 471638D A US471638D A US 471638DA US 471638 A US471638 A US 471638A
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aniline
coloring
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    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; MISCELLANEOUS COMPOSITIONS; MISCELLANEOUS APPLICATIONS OF MATERIALS
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B11/00Diaryl- or thriarylmethane dyes
    • C09B11/04Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
    • C09B11/10Amino derivatives of triarylmethanes
    • C09B11/12Amino derivatives of triarylmethanes without any OH group bound to an aryl nucleus
    • C09B11/20Preparation from other triarylmethane derivatives, e.g. by substitution, by replacement of substituents

Description

* UNITED STATES PATENT Prion.

I BENNO HOMOLKA, OF HOOHSTON-THE-MAIN, GERMANY, ASSIGNOR TO TI-lE FARBWERKE, VORMALS MEISTER, LUCIUS 8t BRUNING, OF SAME PLACE.

PROCESS OF MAKING ROSANILINE DYES.

SPECIFICATION forming part of Letters Patent N 0. 471,638, dated March 29, 1892.

Application filed December 13, 1890. Serial No. 374,616.

(No specimens.) Patented in England December 23, i889, No- 20,678

in France December 23, 1889, No. 202,769; in Belgium December 31, 1889, No. 88,989, and in Italy April 3, 1890, XXIV,

27,054, LIII, 166.

To all whom it may concern:

Be it known that I, BENNO HOMOLKA, doctor of philosophy, a subject of the Emperor of Austria-Hungary, residing at Hochst-on-thel \lain,in the Empire of Germany,have invented certain new and usefullmprovements in the Production of Compounds of the Rosaniline Series, (for which I have received patents in England, No. 20,678, dated December 23, 1889;

10 in France, No. 202,7 69, dated December 23, 1889; in Belgium, No. 88,989, dated December 31, 1889, and in Italy, XXIV, 27 ,054, L111, 166, dated April 3, 1890;) and I do hereby declare the following to be a full, clear, and ex- I 5 act description of the invention, such as will enable others skilled in the art to which it appertains to make and use the same.

This invention relates to theproduction of compounds of the rosaniline series by joint ox- 2o idation of compounds of the diphenylmethan group and aromatic amines, for example:

0 11mm /C6H4NH, T o,n,nn,

OH NH onnNH, (Diamidodiphnyhlietham) (Aniline) (Pararosaniline) The production may be effected by starting with the anhydroformaldehyde amines, O H N::OH themselves causing the two stages of the operation to go on in the same vessel that is to say, first, the formation of the compound of the diphenylmethan group, and, second, the oxidation. Also the formaldehyde maybe introduced into the reaction mass, so 5 that the operation may begin with the formation of the anhydroformaldehyde amine.

The process is more fully explained by the following examples:

EXAMPLE 1.

'len parts, by weight, of anhydroformaldehyde aniline, fifty parts, by weight, of hydrochlorate 0f ortho-toluidine,ten parts,by weight, of aniline, twelveparts,by weight, of nitro-benzole, and one-half part,by weight, of iron filings 45 or the eqivalent quantity of ferrous chloride are heated in an enameled vessel to about 170 centigrade for from two to three hours. Then the aniline and nitro-benzole are driven off by a current of steam and the magenta is precipitated from the solution by means of common salt.

, EXAMPLE 2.

Ten parts, by weight, of diamidodiphenylmethan, thirty parts, by weight, of hydrochlorate of ortho-toluidine, eighteen parts, by 5 5 weight, of ortho-toluidine, twelve parts, by weight, of orthonitrotoluol, and one-half part, by weight, of iron filings (or ferrous chloride) are treated as described in the precedingexample. As oxidizing agents may be employed in the operations described nitro-benzole, orthonitrotoluol, paranitrotoluol, or a mixture of I these compounds; also, nitroxylol, salts of 0x-' ide of iron, arsenical acid, azobenzole, and similar oxidizing agents. 6

EXAMPLE 3.

Production of triphenylrosaniline.As raw material for the production of this body I employ the product resulting from the reaction between formaldehyde and diphenvl- 7o amine in the presence of hydrochloric acid the diphenyldiamido-diphenylmethan. Ten parts, by weight, of diphenyldiamido-diphenylmethan, fifty parts, by weight, of hydrochlorate of diphenylamine, twenty parts, by weight,of dipheny1amine,five parts,byweight, of orthonitrotoluol, and three parts, by weight, of ferrous chloride (iron filings) are heated to 170 for three hours. The melt is treatedhot with alcohol and filtered. From the filtrate on cooling the hydrochlorate of triphenylrosaniline is precipitated in the form of a crystalline mass, which is filtered'and dried.

EXAMPLE 4.

Production of diphenylrosamline.Ten 8: parts, by weight, of diphenyldiamido-diphe- U nylmethan, fifty parts, by weight, of hydrochlorate of ortho-toluidine, twenty parts, by weight, of ortho-toluidine, five parts, by weight, of orthonitrotoluol, and three parts, byweight, c of ferrous chloride (iron filings) are heated on an oil bath to 17 0 centigrade for three hours. The hot mass of the reaction is poured into diluted hydrochloric acid, boiled, and filtered. The residue is hydrochlorate of diphenylros- 5 aniline, which is easily soluble in alcohol or aniline and can be readily converted into sulphonic acids, available commercially as coloring-matters.

In the examples 3 and4 there may be substituted for the diphenyldiamido-diphenylmethan any of the reaction products of formaldehyde with secondary aromatic basesthat is to say, ortho and para tolylphenylamine, ortho-ditolylamine, alpha and beta naphthylphenylarninc, alpha and beta naphthyl-orthotolylamine, or mixtures of two of these bases.

For the diphe'nylamine mentioned in example 3 may be substituted any of the sec ondary bases enumerated above, and for the ortho-toluidine mentioned in example i may be substituted aniline or Xylidine; also for the orthonitrotoluol of examples 3 and 4 may be substituted any of the oxidizing agents hereinbefore mentioned.

The compounds of' the rosaniline series thus prepared are intended for use in dyeing and printing. a

The coloring-matters are in the form of crystalline powder with metallic-green luster.

The alkalized, methylized, and ethylized coloring-matters are soluble in water and alcohol with red to violet coloring. The phenylized coloring-matters are insoluble in water, soluble in alcohol with blue tint. They are all insoluble in ether, chloroform, benzine, and other carburets of hydrogen. In concentrated mineral acids they dissolve with yellow to orangeyellow coloring.

What I claim as my invention, and wish to secure by Letters Patent, is

The process herein described for the production of coloring-matters of the rosaniline series, which consists in treating diamidodiphenylmethan bodies with oxidizing agents in presence of hydrochlorates of aromatic amines, substantially as set forth.

In testimony whereof I atfix my signature in presence of two witnesses.

BENNO HOMOLKA. Witnesses:

J osEF REVERDY, HEINRICH HAHN.

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2542544A (en) * 1948-06-14 1951-02-20 American Cyanamid Co Process of producing polyaryl methane dyes of the rosaniline type
US5922085A (en) * 1997-09-30 1999-07-13 Basf Corporation Preparation of a dye for coloring protein-based fibers and cellulose-based materials from the oxidation products of the manufacture of a triphenylmethane dye

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2542544A (en) * 1948-06-14 1951-02-20 American Cyanamid Co Process of producing polyaryl methane dyes of the rosaniline type
US5922085A (en) * 1997-09-30 1999-07-13 Basf Corporation Preparation of a dye for coloring protein-based fibers and cellulose-based materials from the oxidation products of the manufacture of a triphenylmethane dye

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