DE74699C - Process for the preparation of benzylated azo dyes - Google Patents
Process for the preparation of benzylated azo dyesInfo
- Publication number
- DE74699C DE74699C DENDAT74699D DE74699DA DE74699C DE 74699 C DE74699 C DE 74699C DE NDAT74699 D DENDAT74699 D DE NDAT74699D DE 74699D A DE74699D A DE 74699DA DE 74699 C DE74699 C DE 74699C
- Authority
- DE
- Germany
- Prior art keywords
- dyes
- acid
- dioxynaphthalene
- molecül
- amidoazo
- 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
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000000987 azo dye Substances 0.000 title claims 2
- 239000000975 dye Substances 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 11
- KCXMKQUNVWSEMD-UHFFFAOYSA-N Benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 claims description 7
- 229940073608 benzyl chloride Drugs 0.000 claims description 7
- 150000003460 sulfonic acids Chemical class 0.000 claims description 5
- 210000002268 Wool Anatomy 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 230000001808 coupling Effects 0.000 claims description 3
- 238000010168 coupling process Methods 0.000 claims description 3
- 238000005859 coupling reaction Methods 0.000 claims description 3
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-Nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- -1 sulfobenzyl esters Chemical class 0.000 claims description 2
- UPKAWFACSJWKND-ZXFFUEEESA-J tetrasodium;(6E)-4-amino-6-[[4-[4-[(2Z)-2-(8-amino-1-oxo-5,7-disulfonatonaphthalen-2-ylidene)hydrazinyl]-3-methoxyphenyl]-2-methoxyphenyl]hydrazinylidene]-5-oxonaphthalene-1,3-disulfonate Chemical compound [Na+].[Na+].[Na+].[Na+].C\1=CC2=C(S([O-])(=O)=O)C=C(S([O-])(=O)=O)C(N)=C2C(=O)C/1=N/NC(C(OC)=C1)=CC=C1C1=CC=C(N\N=C\2C(C3=C(N)C(=CC(=C3C=C/2)S([O-])(=O)=O)S([O-])(=O)=O)=O)C(OC)=C1 UPKAWFACSJWKND-ZXFFUEEESA-J 0.000 claims description 2
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims 1
- 241000490025 Schefflera digitata Species 0.000 claims 1
- 239000000980 acid dye Substances 0.000 claims 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- 125000001743 benzylic group Chemical group 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 238000005755 formation reaction Methods 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims 1
- 235000015250 liver sausages Nutrition 0.000 claims 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 1
- CHMBIJAOCISYEW-UHFFFAOYSA-N N-(4-aminophenyl)acetamide Chemical compound CC(=O)NC1=CC=C(N)C=C1 CHMBIJAOCISYEW-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- AGEZXYOZHKGVCM-UHFFFAOYSA-N Benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate dianion Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 230000002378 acidificating Effects 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 239000003638 reducing agent Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/11—Preparation of azo dyes from other azo compounds by introducing hydrocarbon radicals or substituted hydrocarbon radicals on primary or secondary amino groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
- Paper (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Die Amidoazofarbstoffe derThe amidoazo dyes of
Formel NH2-R Formula NH 2 -R
allgemeinengeneral
N=N-R' (wobei N = NR ' (where
unter R1 die Reste von gekuppelten Dioxynaphtalinsulfosäuren zu verstellen sind) werden beim Behandeln mit Benzylchlorid oder analogen Benzylverbindungen in Gegenwart von Alkalien glatt in die entsprechenden Benzylfarbstoffe übergeführt, welche technisch wichtige Vorzüge gegenüber den Ausgangsproducten besitzen.under R 1, the residues of coupled dioxynaphthalene sulfonic acids are to be adjusted) are converted smoothly into the corresponding benzyl dyes on treatment with benzyl chloride or analogous benzyl compounds in the presence of alkalis, which have technically important advantages over the starting products.
Letztere können auf bekannte Weise erhalten werden, wenn man z. B. die Acetylverbindungen von Diaminen bezw. substituirten Diaminen diazotirt, dann die resultirenden Diazoproducte mit Dioxynaphtalinsulfosäuren kuppelt und hierauf die Acetylgruppe abspaltet, oder wenn man, ausgehend von Mononitroverbindungen der Amine bezw. substituirten Amine, deren Diazoderivate mit Dioxynaphtalinsulfosäuren combinirt und nach beendigter Kuppelung die Nitrogruppe durch geeignete Reductionsmittel in die Amidogruppe überführt.The latter can be obtained in a known manner by e.g. B. the acetyl compounds of diamines respectively. substituted diamines are diazotized, then the resulting diazo products couples with dioxynaphthalene sulfonic acids and then splits off the acetyl group, or if one, starting from mononitro compounds of the amines BEZW. substituted amines, their Diazo derivatives combined with dioxynaphthalene sulfonic acids and, after coupling is complete, the Nitro group converted into the amido group by suitable reducing agents.
Von den genannten Ausgangsproducten liefern besonders diejenigen werthvolle Resultate, welche in obigerWeise ausMonoacetyl-p-phenylendiamin bezw. p-Nitranilin und den Sulfosäuren des Ci1 a4-Dioxynaphtalins gewonnen werden.Of the starting products mentioned, particularly those which produce valuable results in the above manner from monoacetyl-p-phenylenediamine and / or. p-Nitraniline and the sulfonic acids of Ci 1 a 4 -Dioxynaphtalins are obtained.
Das Verfahren zur Herstellung dieser neuen Farbstoffe erfolgt allgemein in der Weise, dafs man 1 Molecül der zunächst gebildeten Amidoazopröducte mit 1 Molecül Benzylchlorid bezw. einer analogen Benzylverbindung und 1 Molecül Alkali bezw. Y2 Molecül Alkalicarbonat behandelt.The process for the preparation of these new dyes is generally carried out in such a way that 1 Molecül of the amidoazo products initially formed with 1 Molecül benzyl chloride respectively. an analogous benzyl compound and 1 Molecül alkali BEZW. Y 2 Molecül alkali carbonate treated.
Farbstoff, erhalten durch Benzyliren von p-Amidobenzolazo-ttj c^-dioxynaphtalin-cig-monosulfosäure. Dye obtained from p-amidobenzolazo-ttj by benzyling c ^ -dioxynaphthalene-cig-monosulfonic acid.
38,1 kg des aus Acetyl-p-phenylendiamin durch Diazotiren, Kuppeln mit αΎ ct4-Dioxynaphtalin-a3-monosulfosäure und Abspalten der Acetylgruppe erhältlichen Farbstoffs werden in Wasser gelöst. Nach Zusatz von 12,7 kg Benzylchlorid und 7 kg Potasche schüttelt bezw. rührt man unter gelindem Erwärmen, bis der Geruch des Benzylchlorids vollständig verschwunden ist. Der schwerlösliche Farbstoff wird durch Abfiltriren, Pressen und Trocknen isolirt. Er färbt Wolle in saurem Bade dunkelblau.38.1 kg of the dye obtainable from acetyl-p-phenylenediamine by diazotiring, coupling with α Ύ ct 4 -dioxynaphthalene-a 3 -monosulfonic acid and cleavage of the acetyl group are dissolved in water. After adding 12.7 kg of benzyl chloride and 7 kg of Potasche shakes respectively. The mixture is stirred with gentle warming until the odor of the benzyl chloride has completely disappeared. The sparingly soluble dye is isolated by filtering off, pressing and drying. He dyes wool dark blue in an acid bath.
In ähnlicher Weise erhält man die anderen Farbstoffe, wenn man an Stelle des in vorstehendem Beispiele benutzten Amidoazoproductes die analogen Amidoazoverbindungen aus Ci1 a4-Dioxynaphtalin-a2ßj-disulfosäure bezw. Ct1 a4 - Dioxynaphtalin - ß2 ß3 - disulfosäure verwendet. The other dyes are obtained in a similar manner if, instead of the amidoazo products used in the preceding examples, the analogous amidoazo compounds from Ci 1 a 4 -dioxynaphthalene-a 2 βj-disulfonic acid or. Ct 1 a 4 - dioxynaphthalene - ß 2 ß 3 - disulfonic acid used.
Dieselben erzeugen auf Wolle in saurem Bade rein blaue Nuancen.These produce pure blue nuances on wool in an acidic bath.
An Stelle des Benzylchlorids (1 Molecül) kann man natürlich Benzylbromid oder ähnliche Benzylirungsmittel, an Stelle von Potasche (Y2 Molecül) lassen sich andere Alkalicarbonate (Y2 Molecül) oder auch Aetzalkalien (1 Molecül) verwenden.In place of the benzyl chloride (1 molecule) one can of course use benzyl bromide or similar benzylating agents, instead of potash (Y 2 molecule) other alkali metal carbonates (Y 2 molecule) or caustic alkalis (1 molecule) can be used.
Die so entstehenden Farbstoffe stellen Gemische von den in der französischen Patent-The resulting dyes represent mixtures of the in the French patent
Claims (1)
(worin mit R1 die Reste von gekuppelten Dioxynaphtalinsulfosäuren bezeichnet sind) mit Benzylchlorid bezw. analogen Benzylverbindungen bei Gegenwart von Alkalien behandelt. NH 2 -RN = NR 1
(where R 1 denotes the residues of coupled dioxynaphthalene sulfonic acids) with benzyl chloride and respectively. analogous benzyl compounds treated in the presence of alkalis.
Alkalihydroxyd behandelt.The particular embodiments of the process protected according to claim 1, consisting in that 1 Molecül of those amidoazo dyes which are obtained from monoacetyl - ρ - phenylenediamine or. p-Nitraniline by diazotiring, coupling with Ct 1 a i - dioxynaphthalene - a 3 - monosulfonic acid, U 1 a 4 -dioxynaphthalene-a 2 ßj-disulfonic acid or Ct 1 a 4 -dioxynaphthalene-ß. 2 ß 3 -disulfonic acid and respectively by splitting off the acetyl group. Reduciren the nitro group can be obtained with ι Molecül benzyl chloride or similar Benzylirungsmittel in the presence of V 2 Molecül Alkalica
Treated alkali hydroxide.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE74699C true DE74699C (en) |
Family
ID=347725
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT74699D Expired - Lifetime DE74699C (en) | Process for the preparation of benzylated azo dyes |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE74699C (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6797041B2 (en) | 2002-03-01 | 2004-09-28 | Greenheck Fan Corporation | Two stage air filter |
| US6814783B2 (en) | 2001-03-01 | 2004-11-09 | Phillips Plastics Corporation | Filtration media of porous inorganic particles |
-
0
- DE DENDAT74699D patent/DE74699C/en not_active Expired - Lifetime
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6814783B2 (en) | 2001-03-01 | 2004-11-09 | Phillips Plastics Corporation | Filtration media of porous inorganic particles |
| US6797041B2 (en) | 2002-03-01 | 2004-09-28 | Greenheck Fan Corporation | Two stage air filter |
| US6994743B2 (en) | 2002-03-01 | 2006-02-07 | Greenheck Fan Corporation | Two stage air filter |
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