DE98761C - - Google Patents
Info
- Publication number
- DE98761C DE98761C DENDAT98761D DE98761DA DE98761C DE 98761 C DE98761 C DE 98761C DE NDAT98761 D DENDAT98761 D DE NDAT98761D DE 98761D A DE98761D A DE 98761DA DE 98761 C DE98761 C DE 98761C
- Authority
- DE
- Germany
- Prior art keywords
- acid
- dyes
- solution
- primulin
- diazo compounds
- 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.)
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- 239000000975 dye Substances 0.000 claims description 11
- 150000008049 diazo compounds Chemical class 0.000 claims description 7
- PXUQTDZNOHRWLI-QOPOCTTISA-O Primulin Natural products O(C)c1c(O)c(OC)cc(-c2c(O[C@H]3[C@H](O)[C@@H](O)[C@@H](O)[C@H](CO)O3)cc3c(O)cc(O)cc3[o+]2)c1 PXUQTDZNOHRWLI-QOPOCTTISA-O 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 4
- DYRDKSSFIWVSNM-UHFFFAOYSA-N Acetoacetanilide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1 DYRDKSSFIWVSNM-UHFFFAOYSA-N 0.000 claims description 3
- XYIBRDXRRQCHLP-UHFFFAOYSA-N Ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 claims description 3
- -1 alphyl Chemical group 0.000 claims description 3
- 150000003931 anilides Chemical group 0.000 claims description 3
- CVBUKMMMRLOKQR-UHFFFAOYSA-N 1-phenylbutane-1,3-dione Chemical compound CC(=O)CC(=O)C1=CC=CC=C1 CVBUKMMMRLOKQR-UHFFFAOYSA-N 0.000 claims description 2
- XRTJYEIMLZALBD-UHFFFAOYSA-N 4-(6-methyl-1,3-benzothiazol-2-yl)aniline Chemical compound S1C2=CC(C)=CC=C2N=C1C1=CC=C(N)C=C1 XRTJYEIMLZALBD-UHFFFAOYSA-N 0.000 claims description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N Acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 claims description 2
- 150000001299 aldehydes Chemical class 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 2
- RPAJSBKBKSSMLJ-DFWYDOINSA-N (2S)-2-aminopentanedioic acid;hydrochloride Chemical compound Cl.OC(=O)[C@@H](N)CCC(O)=O RPAJSBKBKSSMLJ-DFWYDOINSA-N 0.000 claims 1
- 239000007900 aqueous suspension Substances 0.000 claims 1
- 150000003388 sodium compounds Chemical class 0.000 claims 1
- 239000000243 solution Substances 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 3
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000005755 formation reaction Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Chemical compound CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical compound C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 125000005594 diketone group Chemical group 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- JWMBNCBSVHSGAW-UHFFFAOYSA-N (2,3-dimethylphenyl)sulfamic acid Chemical compound CC1=CC=CC(NS(O)(=O)=O)=C1C JWMBNCBSVHSGAW-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 210000002268 Wool Anatomy 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 230000001808 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- CRGRWBQSZSQVIE-UHFFFAOYSA-N diazomethylbenzene Chemical compound [N-]=[N+]=CC1=CC=CC=C1 CRGRWBQSZSQVIE-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 229910052500 inorganic mineral Chemical class 0.000 description 1
- 238000009114 investigational therapy Methods 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 239000011707 mineral Chemical class 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 230000001264 neutralization Effects 0.000 description 1
- 230000003472 neutralizing Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid group Chemical class S(N)(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000001043 yellow dye Substances 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/32—Monoazo dyes prepared by diazotising and coupling from coupling components containing a reactive methylene group
- C09B29/322—Monoazo dyes prepared by diazotising and coupling from coupling components containing a reactive methylene group containing acid groups, e.g. COOH, SO3H, PO3H2, OSO3H, OPO2H2; Salts thereof
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Patentschrift;Patent specification;
-JVI 98761- J/1 y/ -JVI 98761- J / 1 y /
KLASSE 22: Farbstoff-, Firnisse, Lacke.CLASS 22: dyes, varnishes, lacquers.
Patentirt im Deutschen Reiche vom a. Juli 1897 ab.Patented in the German Empire from a. July 1897.
Es ist bekannt, dafs Diazobenzöl· auf'Acet-' essigester unter Bildung von Benzolazqacetessig-, ester (vergl. V. Meyer, Ber. X, S. 2075), auf Malonsäureester unter Bildung von Benzolazomalonsäure (vergl. R. Meyer, Ber.'XXI, S. 118; XXIV, S. 1241) reagirt. . 'It is known that diazobenzene on acetone acetic ester with the formation of Benzolazqacetessig-, ester (cf. V. Meyer, Ber. X, p. 2075), on Malonic acid ester with the formation of benzene azomalonic acid (see R. Meyer, Ber.'XXI, p. 118; XXIV, p. 1241) reacts. . '
Diese und einige analog gebildete sogenannte gemischte Azokörper waren ■ .mehrfach Gegenstand der Untersuchung und theoretischer Erörterungen. These and some so-called mixed azo bodies formed in the same way have been the subject of multiple subjects the investigation and theoretical discussions.
Es kamen in allen Fällen, welche durch die Literatur bekannt wurden, als Diazoverbindungen nur Diazobenzol und Diazotoluol, in einer kurzen Notiz von P. Griefs, Ber. XVIII, S. 960, auch die Diazoverbindung von m-Amidobenzoesäure zur Anwendung.In all cases known from the literature, only diazobenzene and diazotoluene were used as diazo compounds, in a brief note from P. Griefs, Ber. XVIII, p. 960, also the diazo compound of m-amidobenzoic acid to use.
Für die Darstellung von Farbstoffen". wurde bisher die Fähigkeit aliphatischen Körper, mit Diazoverbindungen Azokörper zu bilden, nicht benutzt.For the representation of dyes ". Was so far the ability of aliphatic bodies to form azo bodies with diazo compounds has not been achieved used.
Im Allgemeinen liefern nach'unseren Untersuchungen diazotirte Amidosulfosäuren mit den in Betracht kommenden Diketonen wohl Azoverbindungen oder Hydrazone, die aber meist nicht färben' oder als Farbstoffe unbrauchbar sind.In general, according to our investigations, diazotized sulfamic acids give with the diketones that come into consideration are probably azo compounds or hydrazones, but most of them do not dye 'or are useless as dyes.
Wir haben nun gefunden, dafs abweichend davon sehr schöne und brauchbare, meist stark grünstichig gelbe Farbstoffe erhalten werden, wenn solche Derivate des einfachen ß-Ketonaldehyds C H3- C O- C H1. C O ■ H, bei .welchem der Aldehydwasserstoff . durch Alkyl-, Alphyl-, Alkyloxy- oder die Anilidgr.uppe ersetzt ist, mit den Diazoverbindungen der Dehydrothiotoluidin (-xylidin) -sulfosäure und der Primulinsulfosäufe in Reaction gebracht werden.We have now found that, in contrast to this, very beautiful and useful, mostly strongly greenish yellow dyes are obtained when such derivatives of the simple β-ketone aldehyde CH 3 - C O - CH 1 . CO ■ H, with .which the aldehyde hydrogen. is replaced by alkyl, alphyl, alkyloxy or the anilide group, are brought into reaction with the diazo compounds of dehydrothiotoluidine (xylidine) sulfonic acid and primulin sulfonic acid.
Die Darstellung weicht von der für einfache •Azofarbstoffe gebrauchlichen nicht ab.The representation does not differ from that used for simple azo dyes.
Die Diketone werden vor der Kuppelung mit ι Mol. Aetznatron in Lösung gebracht oder aber einfach mit Sodalösung kräftig verrührt. The diketones are brought into solution with ι mol. Caustic soda before coupling or simply vigorously mixed with soda solution.
Als Beispiel für die Darstellung diene folgendes: The following serve as an example for the representation:
34,3 kg dehydrothiotoluidinsulfosaures Natrium werden in gebräuchlicher Weise diazotirt. Die suspendirte Diazoverbindung wird unter Rühren in eine Lösung von 13 kg Acetessigester in 12 kg Natronlauge von 400 B. und 500 kg Wasser, welcher so viel Soda oder Natriumacetat zugesetzt ist, als für Neutralisation der überschüssigen Salzsäure und für die Bildung von Natriumsalz nöthig ist, zulaufen ge- ·■ lassen. .34.3 kg of sodium dehydrothiotoluidinsulfonate are diazotized in the customary manner. The suspended diazo compound is stirred into a solution of 13 kg acetoacetic ester in 12 kg sodium hydroxide solution of 40 ° C. and 500 kg water, to which as much soda or sodium acetate is added as is necessary for neutralizing the excess hydrochloric acid and for the formation of sodium salt , let · ■ run. .
Der gebildete Farbstoff geht mit grünlich gelber Farbe in Lösung. Nach kurzem Rühren wird ausgesalzen. An Stelle von Acetessigester kann Acetylaceton, Benzoylaceton, Acetessiganilid (-toluid) in äquivalenter Menge zur Anwendung kommen.The dye formed goes into solution with a greenish yellow color. After a short stir is salted out. Instead of acetoacetic ester, acetylacetone, benzoylacetone, acetoacetanilide can be used (-toluid) are used in an equivalent amount.
Die Farbstoffe sind hellgelb bis orange gefärbte Pulver. Sie lösen sich leicht in Wasser; etwas schwerer löslich sind die aus Acetessig-^. anilid und -toluid dargestellten. , 1VThe dyes are light yellow to orange colored powders. They easily dissolve in water; Those from acetoacetic acid are somewhat more difficult to dissolve. anilide and toluid shown. , 1 V
Die wässerige Lösung ist bei allen reingelb, erscheint jedoch wenig intensiv gefärbt. Die Farbe der wässerigen Lösung wird durch Zusatz von Soda oder Mineralsäuren nicht ver-"The aqueous solution is pure yellow in all of them, but does not appear very intensely colored. the The color of the aqueous solution is not changed by adding soda or mineral acids "
ändert, durch starkes Aetzalkali wird sie etwas brauner. In cone. Schwefelsäure lösen sich sa'mintliche Farbstoffe mit derselben Nuance wie in Wasser, nur ist die Färbung der Lösung lebhafter. Dieselbe verändert sich beim Erwärmen nicht, mit Ausnahme derjenigen Farbstoffe, welche mit Acetessiganilid (o- und p-toluid) zusammengesetzt sind. Die Lösung dieser Farbstoffe in cone. Schwefelsäure wird bei Erwärmen oder langem Stehen rothorange. Die Farbstoffe färben alle in saurer Lösung Wolle, in neutraler oder schwach alkalischer LösungBaumwolle gelb mit grünstichigerNüancean.changes, through strong caustic alkali it becomes something brown. In cone. Sulfuric acid dissolve similar dyes with the same shade as in water, only the color of the solution is more vivid. The same changes with Do not heat, with the exception of those dyes that contain aceto-aceticanilide (o- and p-toluid) are composed. The solution of these dyes in cone. Sulfuric acid will red-orange when warming or standing for a long time. The dyes all color in acidic solution Wool, in a neutral or weakly alkaline solution Cotton yellow with a greenish nuance.
Claims (1)
i. Verfahren zur Darstellung 'gelber wasch- und lichtechter Farbstoffe, darin bestehend, dafs man solche Derivate des ß-Ketonaldehyds, bei welchen der Aldehydvvasserstoff durch Alkyl-, Alphyl-, Alkyloxy- oder - Anilidgruppe ersetzt ist, als Natriumverbindung in Lösung oder in freiem Zustande, in wässeriger Suspension mit den Diazoverbindungen des sulfurirten Dehydrothiotoluidins (-xylidins), des Primulins in Reaction bringt. Patent claims: ■
i. Process for the preparation of yellow, washable and lightfast dyes, consisting in using those derivatives of β-ketone aldehyde in which the aldehyde hydrogen has been replaced by an alkyl, alphyl, alkyloxy or anilide group, as a sodium compound in solution or in the free state , in aqueous suspension with the diazo compounds of the sulfurized dehydrothiotoluidine (-xylidine) of primulin in reaction.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE98761C true DE98761C (en) |
Family
ID=369703
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| DENDAT98761D Active DE98761C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE98761C (en) |
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