DE205662C - - Google Patents
Info
- Publication number
- DE205662C DE205662C DE1906205662D DE205662DA DE205662C DE 205662 C DE205662 C DE 205662C DE 1906205662 D DE1906205662 D DE 1906205662D DE 205662D A DE205662D A DE 205662DA DE 205662 C DE205662 C DE 205662C
- Authority
- DE
- Germany
- Prior art keywords
- sulfonic acid
- acid
- urea
- hours
- aminonaphthol sulfonic
- 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.)
- Expired - Lifetime
Links
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 8
- 150000003672 ureas Chemical class 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000000975 dye Substances 0.000 description 5
- ZYSOYLBBCYWEMB-UHFFFAOYSA-N 7-aminonaphthalen-1-ol Chemical compound C1=CC=C(O)C2=CC(N)=CC=C21 ZYSOYLBBCYWEMB-UHFFFAOYSA-N 0.000 description 4
- 239000004202 carbamide Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- GKKCIDNWFBPDBW-UHFFFAOYSA-M Potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 229960000583 Acetic Acid Drugs 0.000 description 1
- 241000947840 Alteromonadales Species 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- 150000001913 cyanates Chemical class 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 150000003585 thioureas Chemical class 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
- C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
- C09B31/02—Disazo dyes
- C09B31/08—Disazo dyes from a coupling component "C" containing directive hydroxyl and amino groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Paper (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
ig 205662 - KLASSE 22 a. GRUPPE ig 205662 - CLASS 22 a. GROUP
Zusatz zum Patente 204102 vom 26. April 1906.*)Addendum to patent 204102 of April 26, 1906. *)
Patentiert im Deutschen Reiche vom 29. Juli 1906 ab. Längste Dauer: 25. April 1921.Patented in the German Empire on July 29, 1906. Longest duration: April 25, 1921.
Es wurde gefunden, daß man in dem in dem Hauptpatent 204102 geschilderten Verfahren die als Endkomponente dienende 2 · 5 · 7-Aminonaphtolsulfosäure bzw. deren Acidyl- und Thioharnstoffderivate in vorteilhafter Weise durch ihre unsymmetrischen Harnstoffderivate ersetzen kann, wie sie entweder durch Einwirkung von Phosgen und Ammoniak, oder einfacher von cyansauren Salzen auf 2 · 5 · 7-Aminonaphtolsulfosäure erhalten werden können. Die so erzielten Farbstoffe zeichnen sich vor denen des Hauptpatents teils durch klarere Nuancen, teils durch größere Farbkraft aus. Im folgenden sei die Darstellung der unsymmetrischen Harnstoffderivate und die Farbstoffdarstellung an einem Beispiel erläutert:It has been found that in the process described in the main patent 204102 serving as the end component 2 5 7-aminonaphthol sulfonic acid or its acidyl and thiourea derivatives advantageously through their unsymmetrical urea derivatives can replace, as they are either by the action of phosgene and ammonia, or more simply of cyanate salts on 2 · 5 · 7-aminonaphthol sulfonic acid can be obtained. The dyes obtained in this way are distinguished from those of the main patent in part by being clearer Nuances, partly due to greater color intensity. The following is the representation of the asymmetrical Urea derivatives and the representation of the dye are explained using an example:
a) Unsymmetrischer Harnstoff mittels Phosgen und Ammoniak.a) Unsymmetrical urea using phosgene and ammonia.
12 kg 2 · 5 ■ 7 - Aminonaphtolsulfosäure werden in etwa 250 1 Wasser unter Anwesenheit von 10 kg Soda und 20 kg Ammoniak (25 prozentig) gelöst und bei 40 bis 50 ° solange Phosgen durchgeleitet, bis in einer Probe durch Salzsäure kein Niederschlag mehr entsteht und sich keine Ausgangssäure mehr nachweisen läßt. Man neutralisiert den Ansatz genau mit Salzsäure und sättigt ihn mit Kochsalz. Nach etwa 16 stündigem Rühren filtriert man den ausgeschiedenen symmetrisehen Harnstoff der 2 · 5 · 7 - Aminonaphtolsulfosäure ab. In Lösung verbleibt das unsymmetrische Harnstoffderivat.12 kg 2 · 5 · 7 - aminonaphthol sulfonic acid in about 250 1 water in the presence of 10 kg soda and 20 kg ammonia (25 percent) dissolved and phosgene passed through at 40 to 50 ° until in a sample no more precipitate is formed by hydrochloric acid and no more starting acid can be detected leaves. The approach is precisely neutralized with hydrochloric acid and saturated with table salt. After stirring for about 16 hours the symmetrical urea of 2 · 5 · 7-aminonaphthol sulfonic acid which has separated out is filtered away. The unsymmetrical urea derivative remains in solution.
b) Unsymmetrischer Harnstoff mittels gg Kaliumcyanat.b) Asymmetrical urea by means of gg Potassium cyanate.
24 kg 2 · 5 · 7 - Aminonaphtolsulfosäure werden in etwa 250 1 Wasser und 20 kg Kaliumcyanat gelöst, wobei die Temperatur 50 ° nicht übersteigen soll. Man läßt auf ungefähr 20 ° abkühlen und gibt alsdann 8 kg Eisessig hinzu. Nach etwa 24 stündigem Rühren scheiden sich silbergraue Kristallenen aus, die in warmem Wasser ziemlich leicht löslich sind und mit salpetriger Säure und darauffolgender Behandlung mit Soda nicht mehr die blaue Färbung zeigen, welche Reaktion für die Ausgangssäure unter den gleichen Bedingungen charakteristisch ist.24 kg of 2x5x7-aminonaphthol sulfonic acid are mixed with about 250 liters of water and 20 kg of potassium cyanate dissolved, the temperature should not exceed 50 °. It is left at about 20 ° cool and then add 8 kg of glacial acetic acid. After stirring for about 24 hours, they will separate silver-gray crystals in warm Water are fairly soluble and with nitrous acid and subsequent treatment with soda no longer show the blue color, which reaction for the starting acid is characteristic under the same conditions.
c) Farbstoffdarstellung.c) Dye representation.
Der Farbstoff aus 9,3 kg Anilin und 38 kg p-Aminobenzoyl- 2 · 5 · 7-aminionaphtolsulfosäure wird in etwa 1000 1 Wasser suspendiert und mit 7 kg Nitrit versetzt. Hierzu gibt man 30 kg Salzsäure von 32 Prozent, rührt ungefähr I1Z2 Stunde bei 20 ° gut durch und läßt dann die so gebildete Diazoverbindung inThe dye made from 9.3 kg of aniline and 38 kg of p-aminobenzoyl-2 · 5 · 7-aminionaphthol sulfonic acid is suspended in about 1000 l of water and 7 kg of nitrite are added. To this end, 30 kg of 32 percent hydrochloric acid are added, the mixture is stirred thoroughly for about 1 1 2 hours at 20 ° and the diazo compound thus formed is then left in
4040
4545
5555
*) Früheres Zusatzpatent: 205661.*) Previous additional patent: 205661.
eine Auflösung von 30 kg Soda und 30 kg unsymmetrischen Harnstoff (100 prozentig) der 2 · 5 · 7-Aminonaphtolsulfosäure einfließen. Der Farbstoff scheidet sich als körniger Niederschlag aus. Nach etwa 24 stündigem Rühren wird er abfiltriert, gepreßt und getrocknet.a dissolution of 30 kg of soda and 30 kg of unbalanced Flow in urea (100 percent) of the 2x5x7-aminonaphthol sulfonic acid. Of the The dye separates out as a granular precipitate. After stirring for about 24 hours it is filtered off, pressed and dried.
Claims (1)
Als weitere Ausführungsform des in dem Hauptpatent 204102 geschilderten Verfahrens die Anwendung des unsymmetrischen Harnstoffderivats aus 2-5-7-Aminonaphtolsulfosäure als Endkomponente.Patent claim:
As a further embodiment of the process described in the main patent 204102, the use of the asymmetrical urea derivative of 2-5-7-aminonaphthol sulfonic acid as the end component.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AT44439D AT44439B (en) | 1906-07-28 | 1909-01-29 | Process for the preparation of red disazo dyes. |
Publications (1)
Publication Number | Publication Date |
---|---|
DE205662C true DE205662C (en) |
Family
ID=467895
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE1906205662D Expired - Lifetime DE205662C (en) | 1906-07-28 | 1906-07-28 |
Country Status (1)
Country | Link |
---|---|
DE (1) | DE205662C (en) |
-
1906
- 1906-07-28 DE DE1906205662D patent/DE205662C/de not_active Expired - Lifetime
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