US1813621A - Stable diazo compound of 5-nitro-2-amino-1-methylbenzene - Google Patents
Stable diazo compound of 5-nitro-2-amino-1-methylbenzene Download PDFInfo
- Publication number
- US1813621A US1813621A US288285A US28828528A US1813621A US 1813621 A US1813621 A US 1813621A US 288285 A US288285 A US 288285A US 28828528 A US28828528 A US 28828528A US 1813621 A US1813621 A US 1813621A
- Authority
- US
- United States
- Prior art keywords
- nitro
- methylbenzene
- amino
- diazo compound
- stable
- 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
- 150000008049 diazo compounds Chemical class 0.000 title description 8
- XTTIQGSLJBWVIV-UHFFFAOYSA-N 2-methyl-4-nitroaniline Chemical compound CC1=CC([N+]([O-])=O)=CC=C1N XTTIQGSLJBWVIV-UHFFFAOYSA-N 0.000 title description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 238000004043 dyeing Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical group [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000004753 textile 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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
Definitions
- the present invention relates to a stable diazo compound of 5-nitro-2-amino-l-methylbenzene suitable for dyeing purposes.
- a diazo salt of 5-nitro-2-amino-1-methylbenzene of practically unlimited stability can be obtained in a simple and cheap manner by converting the respective base into its diazoniumborofluoride.
- diazoniumborofluoride of the 5-nitro-2-amino-l-methylbenzene is acompound possessing excellent solubility in water in contradistinction to the diazoniumborofluorides of its homologues and analogues, such as, for instance, the diazoniumborofluorides of t-nitro-2-amino-l-methylbenzene and 4-nitro-1-amino-benzene, which are rather diflicultly soluble in water and therefore unsuitable for the use as stabilized diazo compounds in dyeing processes.
- the following example will illustrate our invention, without limiting it thereto:
- E wampZe .-152 parts by weight of 5-nitro- Q-amino-l-methylbenzene and 1400 parts by weight of water and 700 parts b weight of crude hydrochloric acid are boile for a short time.
- By quickly cooling down the 5-nitro-2- amino l-methylbenzene separates out in a finely divided state and is now diazotized with 69 parts by weight of sodium nitrite at a temperature of from 0 to 10 C.
- the diazo salt is then precipitated from the solution by means of aqueous hydroborofluoric acid, the borofluoride is isolated in the known manner and dried. It is an almost colorless powder; the yield is nearly quantitative.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
atented July 7, 1931 UNITED STATES PATENT; OFFICE \VINFBID HENTBIGH, OF WIESDOEF-ON-THE-RHINE, AND ERNST TIE'IZE, OF COLOGNE- ON-THE-RI-IINE, GERMANY, ASSIGNORS T0 GENERAL ANILINE WORKS, INC., OF NEW YORK, N. Y., A CORPORATION OF DELAWARE STABLE DIAZO COMPOUND 0F 5-NI'1RO-2-AMINO1-METHYLIBENZENE No Drawing. Application filed June 25, 1928, Serial No. 288,285, and in Germany July 18, 1927.
The present invention relates to a stable diazo compound of 5-nitro-2-amino-l-methylbenzene suitable for dyeing purposes.
In accordance with the present invention a diazo salt of 5-nitro-2-amino-1-methylbenzene of practically unlimited stability can be obtained in a simple and cheap manner by converting the respective base into its diazoniumborofluoride.
In the dyeing of textile fibers with azodyestuffs by development on the fiber the use of stabilized diazo compounds is simple and reliable and saves the dyer troublesome process of diazotization.
Since the combinations of diazotized 5- nitro-2-amino-1-methylbenzene and certain arylides of the 2.3-hydroxynaphthoic acid are of outstanding fastness to light and yield especially valuable red shades, the stabilizing of this diazo compound which has now been made possible is particularly important.
The short directions in the German specification No. 281,055 relating to the manufacture of certain diazoniumborofluorides are insufiicient to enable one to predict, how diazo compounds, produced from 5-nitro-2-aminol-methylbenzene (which in contradistinction to other diazo compounds, such as those of aniline, 4;-chloroaniline or -nitraniline, are very easily decomposed) would behave towards borohydrofiuoric acid; it was rather to be expected that the known ready decomposition of the diazonium chloride, sulfate, etc. produced from 5-nitro-2-amino-l-methylbenzene would be encountered again in the di azoniumborofluorides of this base.
Furthermore the diazoniumborofluoride of the 5-nitro-2-amino-l-methylbenzene is acompound possessing excellent solubility in water in contradistinction to the diazoniumborofluorides of its homologues and analogues, such as, for instance, the diazoniumborofluorides of t-nitro-2-amino-l-methylbenzene and 4-nitro-1-amino-benzene, which are rather diflicultly soluble in water and therefore unsuitable for the use as stabilized diazo compounds in dyeing processes. The following example will illustrate our invention, without limiting it thereto:
E wampZe .-152 parts by weight of 5-nitro- Q-amino-l-methylbenzene and 1400 parts by weight of water and 700 parts b weight of crude hydrochloric acid are boile for a short time. By quickly cooling down the 5-nitro-2- amino l-methylbenzene separates out in a finely divided state and is now diazotized with 69 parts by weight of sodium nitrite at a temperature of from 0 to 10 C. The diazo salt is then precipitated from the solution by means of aqueous hydroborofluoric acid, the borofluoride is isolated in the known manner and dried. It is an almost colorless powder; the yield is nearly quantitative.
We claim:
The compound of the probable formula:
being a stable colorless powder, easily soluble in water.
In testimony whereof we have hereunto set our hands.
WINFRID HENTRIGH. [L. s.] ERNST TIETZE. [L. s.]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1813621X | 1927-07-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1813621A true US1813621A (en) | 1931-07-07 |
Family
ID=7744402
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US288285A Expired - Lifetime US1813621A (en) | 1927-07-18 | 1928-06-25 | Stable diazo compound of 5-nitro-2-amino-1-methylbenzene |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US1813621A (en) |
| FR (1) | FR657645A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2423359A (en) * | 1947-07-01 | Diazonium fluosilicates |
-
1928
- 1928-06-25 US US288285A patent/US1813621A/en not_active Expired - Lifetime
- 1928-07-18 FR FR657645D patent/FR657645A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2423359A (en) * | 1947-07-01 | Diazonium fluosilicates |
Also Published As
| Publication number | Publication date |
|---|---|
| FR657645A (en) | 1929-05-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US2496151A (en) | Azo dyestuffs | |
| US1813621A (en) | Stable diazo compound of 5-nitro-2-amino-1-methylbenzene | |
| GB1037981A (en) | New naphthalene monoazo triazine dyestuffs | |
| US2657204A (en) | Azo pigment | |
| US1875243A (en) | Diazo preparations and process of making same | |
| US1590728A (en) | Manufacture of yellow azo dyestuffs | |
| US2194926A (en) | Mono-nitro-benzene compound and the manufacture thereof | |
| US1183378A (en) | Azo dye and process of dyeing. | |
| US2381877A (en) | 1-methoxy-2-amino-4-nitro-5-methylbenzene and process of making the same | |
| US1610936A (en) | Manufacture of yellow azo-dyestuffs | |
| US2437465A (en) | Manufacture of new coloring matters | |
| US1819961A (en) | Azo dyestuffs and process of making same | |
| US2067132A (en) | Solid diazo salts | |
| US2098599A (en) | Yellow substantive dyestuff for cotton | |
| US2136136A (en) | Dyestuffs | |
| US2029647A (en) | Ethylene azo dyestuffs and their manufacture | |
| US2054397A (en) | Azodyestuffs and intermediate | |
| US2122127A (en) | Ortho-hydroxyazo dyes and process for manufacturing the same | |
| US525657A (en) | Paul julius | |
| US1892577A (en) | Derivatives of amino-naphthol sulphonic acids | |
| US2245172A (en) | Process for producing 4-hydroxy-1-aminonaphthalene-8-carboxylic acid and 4-hydroxynaphthostyril | |
| US1871946A (en) | Azo-dyestuffs and process of making same | |
| US2057063A (en) | Azo dyes and their production | |
| US1408296A (en) | Orthooxyazo dyes for wool | |
| US1795125A (en) | Process of producing azo dyestuffs |