DE79082C - Process for the preparation of polyazo dyes from dioxydiphenylmethane - Google Patents
Process for the preparation of polyazo dyes from dioxydiphenylmethaneInfo
- Publication number
- DE79082C DE79082C DENDAT79082D DE79082DA DE79082C DE 79082 C DE79082 C DE 79082C DE NDAT79082 D DENDAT79082 D DE NDAT79082D DE 79082D A DE79082D A DE 79082DA DE 79082 C DE79082 C DE 79082C
- Authority
- DE
- Germany
- Prior art keywords
- mol
- acid
- dye
- mole
- dioxydiphenylmethane
- 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
- 239000000975 dye Substances 0.000 title claims description 41
- 238000000034 method Methods 0.000 title claims 3
- -1 polyazo Polymers 0.000 title claims 2
- 238000002360 preparation method Methods 0.000 title claims 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 18
- 229920000742 Cotton Polymers 0.000 claims description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 claims description 11
- HVBSAKJJOYLTQU-UHFFFAOYSA-N Sulfanilic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 claims description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 229950000244 sulfanilic acid Drugs 0.000 claims description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 239000000843 powder Substances 0.000 claims description 7
- LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate dianion Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 5
- ZUJURJDZOPMJPH-UHFFFAOYSA-M [Cl-].[N-]=[N+]=C1CC=CC=C1 Chemical compound [Cl-].[N-]=[N+]=C1CC=CC=C1 ZUJURJDZOPMJPH-UHFFFAOYSA-M 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 150000008049 diazo compounds Chemical class 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- ZTAFEXGSSLGTTB-UHFFFAOYSA-N (5-sulfo-7-azoniabicyclo[4.1.0]hepta-1(6),2,4-trien-7-ylidene)azanide Chemical compound OS(=O)(=O)C1=CC=CC2=C1[N+]2=[N-] ZTAFEXGSSLGTTB-UHFFFAOYSA-N 0.000 claims description 3
- YIIIFFPJHSEVQN-UHFFFAOYSA-M [Cl-].[N+](=[N-])=C1CC=CC2=CC=CC=C12 Chemical compound [Cl-].[N+](=[N-])=C1CC=CC2=CC=CC=C12 YIIIFFPJHSEVQN-UHFFFAOYSA-M 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- IOVCWXUNBOPUCH-UHFFFAOYSA-M nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims description 3
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 3
- 235000010288 sodium nitrite Nutrition 0.000 claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 3
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-Naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 claims 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 2
- 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 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- 239000000980 acid dye Substances 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- PVVOJFSOAWMYHX-UHFFFAOYSA-N naphthalene-1-carboxylic acid;sodium Chemical compound [Na].C1=CC=C2C(C(=O)O)=CC=CC2=C1 PVVOJFSOAWMYHX-UHFFFAOYSA-N 0.000 claims 1
- 239000001187 sodium carbonate Substances 0.000 claims 1
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 4
- HFACYLZERDEVSX-UHFFFAOYSA-N Benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 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
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 235000002639 sodium chloride Nutrition 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- NPAYBXSLOLNULX-UHFFFAOYSA-N 2-diazo-1H-naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)C(=[N+]=[N-])C=CC2=C1 NPAYBXSLOLNULX-UHFFFAOYSA-N 0.000 description 1
- 229910000906 Bronze Inorganic materials 0.000 description 1
- NRZRRZAVMCAKEP-UHFFFAOYSA-N Naphthionic acid Chemical compound C1=CC=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 NRZRRZAVMCAKEP-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 239000010974 bronze Substances 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 230000001264 neutralization Effects 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004552 water soluble powder 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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/38—Trisazo dyes ot the type
- C09B35/40—Trisazo dyes ot the type the component K being a dihydroxy or polyhydroxy compound
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
In das Molecül des Dioxydiphenylmethans kann nicht nur, wie im Patent Nr. 74629 angegeben wird, eine Azogruppe eingreifen, sondern die Verbindungen der im Patent Nr. 74629 gekennzeichneten Art vermögen sich noch mit einem zweiten Molecül einer Diazoverbindung zu vereinigen, so dafs, wenn auf ι Mol. des genannten Methanderivates 2 Mol. gleicher oder verschiedener Diazoverbindungen zur Einwirkung kommen, in das Molecül des angeführten Körpers zwei Azogruppen eintreten. In the molecule of the dioxydiphenylmethane can not only, as indicated in patent no will intervene, an azo group, but the compounds of the type identified in Patent No. 74629 are capable of each other still to combine with a second molecule of a diazo compound, so that if on ι mol. of the methane derivative mentioned, 2 mol. of the same or different diazo compounds come into play, two azo groups enter the molecule of the body mentioned.
Verwendet man als Diazoverbindungen die Zwischenproducte, die gebildet werden durch Zusammentreten von 1 Mol. Tetrazodiphenyl oder Tetrazoditolyl oder Tetrazodiphenoläther und ι Mol. einer Sulfosäure eines aromatischen Amins, wie z. B. Sulfanilsäure oder Naphtionsäure, so entstehen Farbstoffe, welche die Azogruppe vier Mal enthalten. Die beiden Molecule der Zwischenproducte können entweder gleiche oder verschiedene sein, zudem läfst sich eines derselben durch einen einfachen Diazokörper, wie Diazobenzolchlorid, Diazobenzolsulfosäure oder Diazonaphtalinsulfosäure, ersetzen, in welch letzterem Falle man zu Azofarbstoffen gelangt, welche die Azogruppe drei Mal enthalten. Sämmtliche der genannten Combinationen besitzen noch die Eigenschaft, ungeheizte Baumwolle in alkalischem Bade anzufärben. One uses as diazo compounds the intermediate products that are formed by Accumulation of 1 mol. Tetrazodiphenyl or tetrazoditolyl or tetrazodiphenol ether and ι mol. A sulfonic acid of an aromatic amine, such as. B. sulfanilic acid or naphthionic acid, this creates dyes that contain the azo group four times. The two molecules the intermediate products can either be the same or different, and it can also be one of these by a simple diazo body such as diazobenzene chloride, diazobenzenesulfonic acid or diazonaphthalene sulfonic acid, in the latter case one to azo dyes which contain the azo group three times. All of the combinations mentioned still have the property dyeing unheated cotton in an alkaline bath.
Dem Farbstoff, der z. B. erhalten wird aus ι Mol. Dioxydiphenylmethan, 1 Mol. des Zwischenproductes »Tetrazodiphenyl - Sulfanilsäure« und ι Mol. des Zwischenproductes »Tetrazodiphenyl-Naphtionsäurecc dürfte die folgende Constitutionsformel zukommen:The dye that z. B. is obtained from ι mol. Dioxydiphenylmethane, 1 mol. Des Intermediate products "tetrazodiphenyl sulfanilic acid" and 1 mole of the intermediate product »Tetrazodiphenyl-naphthionic acid is likely to have the following constitutional formula:
CH0 CH 0
Die Constitution des Einwirkungsproductes von Diazonaphtalinchlorid auf Benzidindisazo-,H4-N=N-C10H6-S O3 Na, \NH2 The constitution of the product of action of diazonaphthalene chloride on benzidinedisazo- , H 4 -N = NC 10 H 6 -SO 3 Na, \ NH 2
dioxydiphenylmethan-naphtionsäure wird durch folgendes Schema dargestellt:Dioxydiphenylmethane naphthoic acid is represented by the following scheme:
SO3NaSO 3 Na
CHCH
■N■ N
-.N-C10H7.-.NC 10 H 7 .
I. Farbstoff aus ι Mol. Dioxydiphenylmethan und 2 Mol. Zwischenproduct » Tetrazodiphenyl -I. Dye from ι Mol. Dioxydiphenylmethane and 2 Mol. Intermediate »Tetrazodiphenyl -
Sulfanilsä'ure«.Sulfanilic acid ".
18,4 kg Benzidin werden mit Hülfe von 60 kg Salzsäure von 2 10B. und 13,8 kg Natriumnitrit in gewohnter Weise in die Tetrazoverbindung übergeführt. Dieselbe läfst man alsdann in eine Lösung von 19,5 kg sulfanilsaurem Natron und 40 kg essigsaurem Natron unter gutem Umrühren einfliefsen. Das nach zwei- bis dreistündiger Einwirkungsdauer erhaltene Zwischenproduct trägt man in eine Lösung von ι ο kg Dioxydiphenylmethan, 3,5 kg kaustischer Soda und 50 kg kohlensaurem Natron in 500 1 Wasser ein. Nach kurzem Stehen kocht man auf und salzt den erhaltenen Farbstoff aus. Er stellt getrocknet ein rothbraunes, in heifsem Wasser leicht lösliches Pulver dar und färbt ungeheizte Baumwolle, in alkalischem Bade gelb.18.4 kg of benzidine are converted into the tetrazo compound in the usual way with the aid of 60 kg of hydrochloric acid of 2 1 0 B. and 13.8 kg of sodium nitrite. The same is then allowed to flow into a solution of 19.5 kg of sulfanilic acid soda and 40 kg of acetic acid soda with thorough stirring. The intermediate product obtained after two to three hours of exposure is introduced into a solution of ι o kg of dioxydiphenylmethane, 3.5 kg of caustic soda and 50 kg of carbonate of soda in 500 l of water. After standing for a short time, the mixture is boiled and the dye obtained is salted out. When dried, it is a red-brown powder that is easily soluble in hot water, and it dyes unheated cotton and yellow in an alkaline bath.
Die Lösung des Farbstoffes in concentrirter Schwefelsäure ist rothviolett.The solution of the dye in concentrated sulfuric acid is red-violet.
II. Farbstoff aus Diazobenzolchlorid undII. Dye from diazobenzene chloride and
Benzidin-disazo-dioxydiphenylmethan - Sulfanil-Benzidine-disazo-dioxydiphenylmethane - sulfanil-
säure.acid.
Das nach Beispiel I. dargestellte Zwischenproduct trägt man in eine Lösung von 20 kg Dioxydiphenylmethan, 7 kg kaustischer Soda und 40 kg kohlensaurem Natron in 500 Γ Wasser ein. Nach kurzem Stehen setzt man weitere 40 kg kohlensaures Natron und eine aus 9,3 kg Anilin, 30 kg Salzsäure und 6,9 kg Nitrit dargestellte Lösung von Diazobenzolchlorid hinzu. Nach mehrstündiger Einwirkungsdauer bei gewöhnlicher Temperatur wird zur Vollendung der Reaction auf 60 bis 70° C. erwärmt und abfiltrirt. Der Farbstoff ist in heifsem Wasser sehr schwer löslich und gelangt am besten als Paste zur Verwendung. Derselbe färbt ungeheizte Baumwolle in alkalischem Bade gelb. Die mit diesem Farbstoff erhaltenen Ausfärbungen zeichnen sich vor denjenigen des Congogelbs durch ihre Solidität gegen Säuren und namentlich gegen Alkalien aus.The intermediate product shown according to Example I. is carried in a solution of 20 kg Dioxydiphenylmethane, 7 kg of caustic soda and 40 kg of carbonate of soda in 500 Γ Water a. After standing for a short time, add another 40 kg of carbonate of soda and one solution of diazobenzene chloride prepared from 9.3 kg of aniline, 30 kg of hydrochloric acid and 6.9 kg of nitrite added. After several hours of exposure at normal temperature is heated to 60 to 70 ° C. and filtered off to complete the reaction. The dye is very sparingly soluble in hot water and is best used as a paste. It dyes unheated cotton yellow in an alkaline bath. The ones with this dye The colorations obtained stand out from those of the Congo yellow by their solidity against acids and especially against alkalis.
Die Lösung des Farbstoffes in concentrirter Schwefelsäure ist braun.The solution of the dye in concentrated sulfuric acid is brown.
III. Farbstoff aus Diazobenzolsulfosäure undIII. Diazobenzenesulfonic acid and dye
Benzidin-disazo-dioxydiphenylmethan - Sulfanil-Benzidine-disazo-dioxydiphenylmethane - sulfanil-
säure.acid.
Zur Darstellung dieses Farbstoffes ersetzt man in obigem Beispiel die 9,3 kg Anilin durch 19,5 kg sulfanilsaures Natron. Der erhaltene Farbstoff ist in heifsem Wasser sehr leicht löslich und läfst sich nur aus neutraler Lösung mit viel Kochsalz ausfällen. Getrocknet stellt er ein dunkelbraunes Pulver dar, das ungeheizte Baumwolle in alkalischem Bade, am besten unter Zusatz von Kochsalz, gelbbraun färbt.To represent this dye, the 9.3 kg of aniline in the above example are replaced by 19.5 kg of sulphanilic sodium bicarbonate. The dye obtained is very light in hot water soluble and can only be precipitated from a neutral solution with a lot of table salt. Dried notes it is a dark brown powder, the unheated cotton in an alkaline bath, am best with the addition of table salt, turns yellow-brown.
Die Lösung des Farbstoffes in concentrirter Schwefelsäure ist braun.The solution of the dye in concentrated sulfuric acid is brown.
IV. Farbstoff aus 1 Mol. Dioxydiphenylmethan und 2 Mol. Zwischenproduct »Tetrazodiphenyl-Naphtionsäure« (Patent Nr. 39096).IV. Dye from 1 mol. Dioxydiphenylmethane and 2 mol. Intermediate product "Tetrazodiphenyl-naphthoic acid" (Patent No. 39096).
Man ersetzt in Beispiel I. die 19,5 kg sulfanilsaures Natron durch 24,5 kg naphtionsaures Natron.The 19.5 kg of sulphanilic acid are replaced in Example I. Soda through 24.5 kg of naphthoic acid soda.
Der getrocknete Farbstoff stellt ein dunkelbraunes, bronzeglänzendes, in heifsem Wasser leicht lösliches Pulver dar; er färbt ungeheizte Baumwolle in alkalischem Bade ponceauroth.The dried dye is dark brown, shiny bronze in hot water easily soluble powder; he dyes unheated cotton in an alkaline bath ponceauroth.
Die Lösung des Farbstoffes in concentrirter Schwefelsäure ist blau.The solution of the dye in concentrated sulfuric acid is blue.
V. Farbstoff aus 1 Mol. Dioxydiphenylmethan und 2 Mol. Zwischenproduct »Tetrazoditolyl-Naphtionsäure« (Patent Nr. 39096).V. Dye from 1 mol. Dioxydiphenylmethane and 2 mol. Intermediate product "Tetrazoditolyl-Naphthionic acid" (Patent No. 39096).
Man ersetzt in Beispiel I. die 18,4 kg Benzidin durch 2i,3 kg Tolidin und die 19,5 kg sulfanilsaures Natron durch 24,5 kg naphtionsaures Natron.In Example I, the 18.4 kg of benzidine are replaced by 21.3 kg of tolidine and the 19.5 kg of sulfanilic acid Soda through 24.5 kg of naphthoic acid soda.
Der getrocknete Farbstoff bildet ein braunes, bronzeglänzendes, in heifsem Wasser leicht lösliches Pulver; er färbt ungeheizte Baumwolle in alkalischem Bade gelbroth.The dried dye forms a brown, bronze-shimmering color that is light in hot water soluble powder; he dyes unheated cotton yellow-red in an alkaline bath.
Die Lösung des Farbstoffes in concentrirter Schwefelsäure ist blau.The solution of the dye in concentrated sulfuric acid is blue.
VI. Farbstoff aus 1 Mol. Dioxydiphenylmethan , ι Mol. Tetrazodiphenyl-Sulfanilsäure und ι Mol. Tetrazodiphenyl - Naphtionsäure (Patent Nr. 39096).VI. Dye from 1 mol. Dioxydiphenylmethane, ι mol. Tetrazodiphenyl-sulfanilic acid and ι Mol. Tetrazodiphenyl - naphthionic acid (Patent No. 39096).
Die nach Beispiel II. erhaltene Benzidindisazo-dioxydiphenylmethan-Sulfanilsäure wird mit 40 kg kohlensaurem Natron versetzt; zu dieser Mischung fügt man alsdann das Zwischenproduct Tetrazodiphenyl - Naphtionsäure, erhalten aus 18,4 kg Benzidin, 60 kg Salzsäure, 13,8 kg Nitrit, 24,5 kg naphtionsaurem Natron und 40 kg essigsaurem Natron. Die Reactionsmasse wird nach einigem Stehen aufgekocht und der gebildete Farbstoff ausgesalzen. Er stellt getrocknet ein dunkelbraunes, in heifsem Wasser leicht lösliches Pulver dar und färbt ungeheizte Baumwolle in alkalischem Bade gelbroth.The benzidinedisazo-dioxydiphenylmethane-sulfanilic acid obtained according to Example II 40 kg of carbonate of soda are added; the intermediate product is then added to this mixture Tetrazodiphenyl naphthoic acid, obtained from 18.4 kg benzidine, 60 kg hydrochloric acid, 13.8 kg of nitrite, 24.5 kg of naphthoic acid soda and 40 kg of acetic acid soda. The reaction mass is boiled after standing for a while and the dye formed is salted out. He puts a dried dark brown, in hot Water is a readily soluble powder and dyes unheated cotton in an alkaline bath yellow-red.
Die Lösung des Farbstoffes in concentrirter Schwefelsäure ist grauviolett.The solution of the dye in concentrated sulfuric acid is gray-violet.
VII. Farbstoff aus 1 Mol. Dioxydiphenylmethan, ι Mol. Tetrazoditolyl - Naphtionsäure (Patent Nr. 39096) und 1 Mol. Tetrazodiphenol-methyl-VII. Dye from 1 mol. Dioxydiphenylmethane, ι mol. Tetrazoditolyl - naphthoic acid (patent No. 39096) and 1 mole of tetrazodiphenol-methyl-
äther-Naphtionsäure.ether naphthoic acid.
Man stellt zunächst Tolidin-disazo-dioxydiphenylmethan-Naphtionsäure dar; man erhält diese Verbindung nach dem im Beispiel I. angegebenen Verfahren aus 21,2 kg Tolidin, 60 kgTolidine-disazo-dioxydiphenylmethane-naphthoic acid is first prepared dar; this compound is obtained by the method given in Example I. from 21.2 kg of tolidine, 60 kg
Claims (4)
und Tolidin-disazo-dioxydiphenylmethan-IX. Α-Diazonaphthalene sulfonic acid dye
and tolidine-disazo-dioxydiphenylmethane
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE79082C true DE79082C (en) |
Family
ID=351744
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT79082D Expired - Lifetime DE79082C (en) | Process for the preparation of polyazo dyes from dioxydiphenylmethane |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE79082C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3552371A (en) * | 1968-02-09 | 1971-01-05 | Edward W Kahelin | Baseball pitching machine |
-
0
- DE DENDAT79082D patent/DE79082C/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3552371A (en) * | 1968-02-09 | 1971-01-05 | Edward W Kahelin | Baseball pitching machine |
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