USRE13969E - Ors to farbwerke vorm - Google Patents
Ors to farbwerke vorm Download PDFInfo
- Publication number
- USRE13969E USRE13969E US RE13969 E USRE13969 E US RE13969E
- Authority
- US
- United States
- Prior art keywords
- acid
- violet
- ors
- red
- blue
- Prior art date
Links
- 239000002253 acid Substances 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 238000000034 method Methods 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 150000004961 triphenylmethanes Chemical class 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 239000003518 caustics Substances 0.000 description 4
- 239000007859 condensation product Substances 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 230000001590 oxidative Effects 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- DLGBEGBHXSAQOC-UHFFFAOYSA-N 2-hydroxy-5-methylbenzoic acid Chemical compound CC1=CC=C(O)C(C(O)=O)=C1 DLGBEGBHXSAQOC-UHFFFAOYSA-N 0.000 description 2
- MXKBHIPOOQSROI-UHFFFAOYSA-N 3-bromo-4-tert-butylaniline;hydrochloride Chemical compound Cl.CC(C)(C)C1=CC=C(N)C=C1Br MXKBHIPOOQSROI-UHFFFAOYSA-N 0.000 description 2
- AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 2
- 241001274613 Corvus frugilegus Species 0.000 description 2
- 210000002268 Wool Anatomy 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 description 2
- 238000003801 milling Methods 0.000 description 2
- 239000011664 nicotinic acid Substances 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N nicotinic acid Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- 235000001968 nicotinic acid Nutrition 0.000 description 2
- 230000001376 precipitating Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
Definitions
- one molecule of the said o-oxycarboxylic acid may be replaced by such a molecule wherein the para position is occupied, so that there may be used as parent material asyimnetrical condensation-pinch nets in which the reaction of the aldehyde with the oxycarboxylic acid has occurred on the one hand in )ara- )osition, andon the other hand in ortho-position, to the hydroxyl group of the oxyarylcarboxylic acid.
- the said parent material has the following general formula:
- the newdyestuifs have the general for- HO (iOOH )Vhen dry, they form dark powders soluble in caustic alkalis to red to violet-red solutions; on adding acetic acid they are precipitated from these solutions in violet to blue flakes. Their solution in concentrated sulfuric acid is yellowish-red and yields, on adding water, violet to blue flakes.
- the dyeings 011 wool in an acid bath are of a dull grayish-violet tint and when subsequently chromed they turn pure violet to blue; these dyeings are of excellent fastness to washing and milling.
- I-Ilg stands for a halogen atom
Description
UNITED STATES PATENT OFFICE.
AUGUST STOCK A D FRIEDRICH HEIM, or HooHs -oN-THE-MAIN, GE MANY, ASSIGN- oRs To FABBWERKE voR MEISTER ooms & BRt'INING, oF HooHsT-oN-THE- MAIN, GERMANY, A CORPORATION OF GERMANY. r
DYESTUFFS OF THE TRIPHENYLMETHANE SERIES AND PROCESS OF MAKING SAME.
To all whom it may concern Be it known that we, AUGUST S'rooK, Ph.
' D., chemist, and FRIEDRICH HETM, Ph. D.,
chemist, citizens of the Empire of Germany,
residing at Hochst-on-the-Main, Germany,
have invented certain new and useful Im provements in Dyestuffs of the Triphenylmethane Series and Processes of Making Same, of which the following is a specification.
As described in our U. S. Patent No. 995,49l and 'in our U. S. patent application Ser. No. 578,649 filed 24th August 1910, there are obtained dyestuffs of the triphenylmethane series capable of being subsequently chromed, by heating withan aromatic base the dyestuds produced by condensing a p-halogenbcnzaldehyde, or a substitution-product, thereof with an orthooxyarylcarboxylic acid, oxidizing the condensation product. ,For the preparation of these condensation-products, there were hithe'rto used only o-oxycarboxylic acids having the para-position free, so that the condensation with the aldehyde occurred in para-position to the hydroxyl group. Now according to our present invention one molecule of the said o-oxycarboxylic acid may be replaced by such a molecule wherein the para position is occupied, so that there may be used as parent material asyimnetrical condensation-pinch nets in which the reaction of the aldehyde with the oxycarboxylic acid has occurred on the one hand in )ara- )osition, andon the other hand in ortho-position, to the hydroxyl group of the oxyarylcarboxylic acid. The said parent material has the following general formula:
n O I i wherein Hlg stands for a halogen atom, and wherein the hydrogen-atoms of the and subsequently Specification of Reissued Letters Patent. Reissued Aug 24, 1915,
dated June, 24, 131 3, Serial No. 711,101.
Serial No. 38,800}
Application for reissue filed The newdyestuifs have the general for- HO (iOOH )Vhen dry, they form dark powders soluble in caustic alkalis to red to violet-red solutions; on adding acetic acid they are precipitated from these solutions in violet to blue flakes. Their solution in concentrated sulfuric acid is yellowish-red and yields, on adding water, violet to blue flakes.
The dyeings 011 wool in an acid bath are of a dull grayish-violet tint and when subsequently chromed they turn pure violet to blue; these dyeings are of excellent fastness to washing and milling.
Example: One part of the product, obtained in the usual manner by condensing equal molecular proportions of p-chlorbenzaldehyde, m-cresotinie acid, and p-cresotinic acid and subsequently oxidizing, is heated to l20 C. for,{1 hour with 5 parts of anilin and one part of anilin hydrochlorid. The mass is then poured into an excess 'of diluted.hydrochloric acid for precipitating the dyestufi' which is then filtered, washed and dried. The, dyestuif has the formula It gives dyeings which, after being chromed, are of a much greener tint than those prostuffs of the triphenyhnethane series, capa- I wherein tinic acid.
Having now. described our invention,
what we claim is: 1 v
1. 'The process of manufacturlng dyeble of being subsequently chromed, which consists in heating with an aromatic base a dyestuff of the. general formula:
wherein I-Ilg stands for a halogen atom; v
being, when dry, a dark powder soluble 1n 'causticalkahs to. red solutions from which 2. As new produts, the dyestuffs ofthe formulaz";
l stands for anaryl residue, .be-
in g, when dry, dark powders soluble in caustic alkalis to' red to violet-red solutions from which on'the additioncf acetic acid theylare precipitated in violet-to blue flakes,
. their solution in concentrated sulfuric acid being yellowish led yielding violet toblue .dull violet to blue tints and, on bein'g subse- .quently chromed, pure violet to blue tints of .great fastness.
formula I 3'. As a new product, the dyestufi ofthe on the addition ofacetic acid it is precipitated in blue flakes; ts solutionin concentrated sulfuric acld being yellowish-red AUGUST STOCK.v FRIEDRICH HEIM;
)Vitne sses; I
JEAN GRUND,
ROBERT VSCHMIDLIN.
Family
ID=
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