DE165102C - - Google Patents
Info
- Publication number
- DE165102C DE165102C DE1904165102D DE165102DA DE165102C DE 165102 C DE165102 C DE 165102C DE 1904165102 D DE1904165102 D DE 1904165102D DE 165102D A DE165102D A DE 165102DA DE 165102 C DE165102 C DE 165102C
- Authority
- DE
- Germany
- Prior art keywords
- acid
- sulfonic acid
- dyes
- oxy
- parts
- 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
- 239000000987 azo dye Substances 0.000 claims description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 2
- 150000001721 carbon Chemical class 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 239000002253 acid Substances 0.000 description 12
- 239000000975 dye Substances 0.000 description 8
- 229920000742 Cotton Polymers 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 150000008049 diazo compounds Chemical class 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 210000002268 Wool Anatomy 0.000 description 3
- 230000002378 acidificating Effects 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- HFACYLZERDEVSX-UHFFFAOYSA-N Benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- NUIURNJTPRWVAP-UHFFFAOYSA-N Tolidine Chemical compound C1=C(N)C(C)=CC(C=2C=C(C)C(N)=CC=2)=C1 NUIURNJTPRWVAP-UHFFFAOYSA-N 0.000 description 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 2
- 239000001045 blue dye Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000000875 corresponding Effects 0.000 description 2
- -1 diazophenol ethers Chemical class 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-Naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 1
- JRBJSXQPQWSCCF-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine Chemical compound C1=C(N)C(OC)=CC(C=2C=C(OC)C(N)=CC=2)=C1 JRBJSXQPQWSCCF-UHFFFAOYSA-N 0.000 description 1
- NXTNASSYJUXJDV-UHFFFAOYSA-N 3-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=CC(C(Cl)=O)=C1 NXTNASSYJUXJDV-UHFFFAOYSA-N 0.000 description 1
- MCPLVIGCWWTHFH-UHFFFAOYSA-L Methyl blue Chemical compound [Na+].[Na+].C1=CC(S(=O)(=O)[O-])=CC=C1NC1=CC=C(C(=C2C=CC(C=C2)=[NH+]C=2C=CC(=CC=2)S([O-])(=O)=O)C=2C=CC(NC=3C=CC(=CC=3)S([O-])(=O)=O)=CC=2)C=C1 MCPLVIGCWWTHFH-UHFFFAOYSA-L 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J Tin(IV) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- ZUJURJDZOPMJPH-UHFFFAOYSA-M [Cl-].[N-]=[N+]=C1CC=CC=C1 Chemical compound [Cl-].[N-]=[N+]=C1CC=CC=C1 ZUJURJDZOPMJPH-UHFFFAOYSA-M 0.000 description 1
- JTDHPBVHCNWIEK-UHFFFAOYSA-N [N-]=[N+]=CC(=O)NC1=CC=CC=C1 Chemical compound [N-]=[N+]=CC(=O)NC1=CC=CC=C1 JTDHPBVHCNWIEK-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000000980 acid dye Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010411 cooking Methods 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
- 239000000835 fiber Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 230000001264 neutralization Effects 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 150000002832 nitroso derivatives Chemical class 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 239000003638 reducing agent Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000001187 sodium carbonate Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 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
- 159000000000 sodium salts Chemical class 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/60—Naphthoxazoles; Hydrogenated naphthoxazoles
-
- 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
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Es wurde gefunden, daß man aus den Naphtoxazoloxysulfosäuren der allgemeinen Formel:It has been found that the naphtoxazoloxysulfonic acids of the general Formula:
N=C-RN = C-R
. I. I.
SO, HSO, H
OHOH
in der R Wasserstoff oder ein aliphatisches oder aromatisches Radikal bedeutet, durch Kombination mit Diazoverbindungen wertvolle Farbstoffe erhalten kann, die sich durch ihre klaren Nuancen auf Wolle und Baumwolle und ihre Echtheit gegen Säuren, Alkalien und Licht auszeichnen.in which R is hydrogen or an aliphatic or aromatic radical, valuable dyes can be obtained through combination with diazo compounds, which are distinguished by their clear nuances on wool and cotton and their fastness to acids, alkalis and light.
Die oben erwähnten Naphtoxazole werdenThe above mentioned naphtoxazoles are
ao z. B. dargestellt durch die Einwirkung von Säureanhydriden oder -Chloriden auf die ι - Amido -2 · 5 - dioxynaphtalin -7- sulfosäure. Die Darstellung der Azofarbstoffe erfolgt nach den üblichen Methoden.ao z. B. represented by the action of acid anhydrides or chlorides on the ι - Amido -2 · 5 - dioxynaphthalene -7- sulfonic acid. The azo dyes are represented according to the usual methods.
Die aus 2 · 5-Dioxynaphtalin -7- sulfosäure durch Behandeln mit Nitrit in essigsaurer Lösung erhaltene Nitrosoverbindung wird mit Zinnchlorür und Salzsäure oder Zinkstaub reduziert, die ausgeschiedene Amidodioxynaphtalinsulfosäure wird abnitriert und durch Auflösen mit Soda und heißem Wasser, schnelle Filtration der Lösung und Wiederausfällen aus dem Filtrate gereinigt. Diese Säure, die im trockenen Zustande ein farbloses Pulver bildet, und deren alkalische Lösung an der Luft rasch Sauerstoff unter Violettfärbung aufnimmt, wird mit der doppelten Menge Essigsäureanhydrid mehrere Stunden unter Rückfluß gekocht und darauf das unveränderte Anhydrid und die Essigsäure abdestilliert. Der Rückstand ist farblos in überschüssiger Soda löslich. Aus der Lösung wird durch Salzsäure die ju-Methyl-ι · 2-naphtoxazol~5-oxy-7-sulfosäure abgeschieden, die beim Kochen mit Säuren keine Veränderung mehr erleidet. Sie vereinigt sich in alkalischer Lösung mit den einfachen Diazoverbindungen der Benzolreihe zu klaren roten Farbstoffen, die Wolle und Baumwolle anfärben. Mit Diazophenoläthern, Diazonaphtalmen und Diazoacetanilid werden blaurote Produkte erhalten. The from 2 · 5-dioxynaphthalene-7-sulfonic acid by treatment with nitrite in acetic acid Solution obtained nitroso compound is made with tin chloride and hydrochloric acid or zinc dust reduced, the excreted amidodioxynaphthalene sulfonic acid is nitrated and by dissolving with soda and hot water, rapid filtration of the solution and reprecipitation purified from the filtrate. This acid, which in the dry state is colorless Powder forms, and their alkaline solution in the air rapidly absorbs oxygen If violet color takes up, double the amount of acetic anhydride becomes several Boiled under reflux for hours and then the unchanged anhydride and acetic acid distilled off. The residue is colorless and soluble in excess soda. From the Solution is the ju-methyl-ι by hydrochloric acid 2-naphtoxazole ~ 5-oxy-7-sulfonic acid deposited, which no longer undergoes any change when cooking with acids. It combines in an alkaline solution with the simple ones Diazo compounds of the benzene series to clear red dyes, wool and cotton stain. With diazophenol ethers, diazonaphtalms and diazoacetanilide, blue-red products are obtained.
30 Teile der μ-Methyl-1· 2-naphtoxazol-5-oxy-7-sulfosäure werden z. B. in 30 Teilen Soda und Wasser gelöst, in dieser Lösung mit einer Diazolösung aus 9,3 Teilen Anilin vereinigt und der Farbstoff in der üblichen Weise isoliert. Er färbt Wolle und Baumwolle orangerot. Der Farbstoff aus Benzidin und 2 Mol. der μ- Methyl-1 · 2-naphtoxazol-5-oxy-7-sulfosäure färbt Baumwolle violett, derjenige aus Benzidin und 1 Mol. Salicylsäure und I Mol. dieser Säure rot.30 parts of μ- methyl-1 · 2-naphtoxazole-5-oxy-7-sulfonic acid are z. B. dissolved in 30 parts of soda and water, combined in this solution with a diazo solution of 9.3 parts of aniline and the dye isolated in the usual manner. It dyes wool and cotton orange-red. The dye made from benzidine and 2 mol. Of μ- methyl-1 · 2-naphthoxazole-5-oxy-7-sulfonic acid turns cotton violet, the one made from benzidine and 1 mol. Salicylic acid and 1 mol. Of this acid turns red.
40 Teile der nach Beispiel 1 dargestellten Amidodioxynaphtalinsulfosäure werden mit Soda in etwa 800 Teilen Wasser von 40 bis 500 neutral bis schwach sauer aufgelöst und unter gutem Rühren mit 30 Teilen fein40 parts of the Amidodioxynaphtalinsulfosäure prepared according to Example 1 are dissolved with sodium carbonate in 800 parts of water of 40 to 50 0 neutral to slightly acidic and finely with vigorous stirring to 30 parts of
pulverisiertem m-Nitrobenzoylchlorid und abwechselnd mit etwas Soda allmählich versetzt, so daß die Reaktion der Flüssigkeit immer schwach sauer bleibt. Wenn eine herausgenommene Probe sich durch Sodazusatz an der Luft nicht mehr violett färbt, ist die Reaktion beendet. Man kocht auf, macht mit Salzsäure mineralsauer, kocht kurze Zeit, läßt erkalten und filtriert die ausgeschiedene μ -Nitrophenyl -1 · 2-naphtoxazol-5-oxy-7-sulfosäure ab. Diese Säure vereinigt sich mit Diazoverbindungen zu klaren Farbstoffen, die etwas röter bezw. blauer färben als die entsprechenden Produkte aus der in Beispiel 1 genannten Methylnaphtoxazoloxysulfosäure. pulverized m-nitrobenzoyl chloride and alternately with a little soda gradually added so that the reaction of the liquid always remains slightly acidic. If a sample that has been taken out no longer turns purple when exposed to soda, the reaction has ended. It is boiled up, made mineral acid with hydrochloric acid, boiled for a short time, allowed to cool and the precipitated μ -nitrophenyl -1 · 2-naphtoxazole-5-oxy-7-sulfonic acid is filtered off. This acid combines with diazo compounds to form clear dyes, which are a little redder and. Blue in color than the corresponding products from the methylnaphtoxazole oxysulfonic acid mentioned in Example 1.
So färben z. B. die Farbstoffe aus Tolidin oder Dianisidin und 2 Mol. dieser Säure ungebeizte Baumwolle blaustichig violett. Beim Behandeln mit reduzierenden Agentien geht die ju-Nitrophenyl-i · 2 - naphtoxazol-5-oxy-7-sulfosäure in die entsprechende Amidoverbindung über, für deren Darstellung folgendes Beispiel diene:So color z. B. the dyes from tolidine or dianisidine and 2 moles of this acid unpickled Cotton with a bluish purple tinge. When treated with reducing agents, the ju-nitrophenyl-i · 2-naphtoxazole-5-oxy-7-sulfonic acid goes into the corresponding amido compound, for their representation the following Example serve:
Die gemäß Beispiel 2 erhaltene Nitrosäure wird neutral aufgelöst und unter fortwährendem Rühren in ein kochendes Gemisch von 100 Teilen Eisenpulver, 500 Teilen Wasser und 3 Teilen Schwefelsäure eingetragen. Das Reaktionsgemisch soll immer schwach sauer bleiben, was durch Zusatz von Schwefelsäure erreicht wird. Nach dreistündigem Kochen wird alkalisch gemacht, abnitriert und aus dem Filtrate die ju-Amidophenyl-i · 2-naphtoxazol-5-oxy-7-sulfosäure als Natronsalz mit Kochsalz abgeschieden.The nitro acid obtained according to Example 2 is dissolved neutrally and continuously Stir in a boiling mixture of 100 parts iron powder, 500 parts water and 3 parts of sulfuric acid entered. The reaction mixture should always remain slightly acidic, which is achieved by adding sulfuric acid is achieved. After three hours of boiling, it is made alkaline and nitrated and from the filtrate the ju-amidophenyl-i · 2-naphtoxazole-5-oxy-7-sulfonic acid deposited as sodium salt with common salt.
Wird diese Säure in bekannter Weise mit Diazoverbindungen vereinigt, so entstehen klare rote bis violette bis blaue Farbstoffe, die die Baumwolle direkt anfärben und auf der Faser durch aufeinander folgende Behandlung mit salpetriger Säure und ß-Naphtol in waschechte und lichtechte, klare, rote bis blaue Farbstoffe übergehen.If this acid is combined with diazo compounds in a known manner, it is formed clear red to purple to blue dyes that dye the cotton directly and on the fiber by sequential treatment with nitrous acid and ß-naphtol pass into washfast and lightfast, clear, red to blue dyes.
Der Farbstoff, erhalten durch Kuppeln des Zwischenproduktes aus Tolidin und 1 Mol. der ju -Amidophenyl -1 · 2 -naphtoxazol -5- oxy-7-sulfosäure mit ι Mol. ι · 8-Dioxynaphtalin-3 · 6-disulfosäure färbt die Baumwolle blau, derjenige aus der diazotierten Amidoazoverbindung, die aus Diazobenzolchlorid und i-Naphtylamin-7-sulfosäure entsteht, und der oben erwähnten Amidophenyloxazoloxysulfosäure färbt violettblau.The dye obtained by coupling the intermediate of tolidine and 1 mole. of ju amidophenyl -1 · 2 -naphtoxazole -5-oxy-7-sulfonic acid with ι mol. ι · 8-dioxynaphthalene-3 6-disulfonic acid dyes cotton blue, the one from the diazotized amidoazo compound, which arises from diazobenzene chloride and i-naphthylamine-7-sulfonic acid, and the above-mentioned amidophenyloxazole oxysulfonic acid turns violet-blue.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT27463D AT27463B (en) | 1904-02-25 | 1905-10-20 | Process for the preparation of azo dyes. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE165102C true DE165102C (en) |
Family
ID=430633
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1904165102D Expired - Lifetime DE165102C (en) | 1904-02-25 | 1904-02-25 |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE165102C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3183231A (en) * | 1963-07-17 | 1965-05-11 | American Cyanamid Co | Cyanonaphthoxazole brighteners |
-
1904
- 1904-02-25 DE DE1904165102D patent/DE165102C/de not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3183231A (en) * | 1963-07-17 | 1965-05-11 | American Cyanamid Co | Cyanonaphthoxazole brighteners |
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