CH210831A - Process for the preparation of a chromable dye of the triarylmethane series. - Google Patents
Process for the preparation of a chromable dye of the triarylmethane series.Info
- Publication number
- CH210831A CH210831A CH210831DA CH210831A CH 210831 A CH210831 A CH 210831A CH 210831D A CH210831D A CH 210831DA CH 210831 A CH210831 A CH 210831A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- chromable
- preparation
- hours
- diethylamino
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000000975 dye Substances 0.000 claims description 12
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 7
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 6
- FHMMQQXRSYSWCM-UHFFFAOYSA-N 1-aminonaphthalen-2-ol Chemical compound C1=CC=C2C(N)=C(O)C=CC2=C1 FHMMQQXRSYSWCM-UHFFFAOYSA-N 0.000 claims description 4
- 150000008064 anhydrides Chemical class 0.000 claims description 3
- 239000000987 azo dye Substances 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- 210000002268 wool Anatomy 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims 2
- 230000005494 condensation Effects 0.000 claims 2
- 238000010438 heat treatment Methods 0.000 claims 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000003929 acidic solution Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-N methyl sulfate Chemical compound COS(O)(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-N 0.000 description 1
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-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
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
- C09B11/10—Amino derivatives of triarylmethanes
- C09B11/24—Phthaleins containing amino groups ; Phthalanes; Fluoranes; Phthalides; Rhodamine dyes; Phthaleins having heterocyclic aryl rings; Lactone or lactame forms of triarylmethane dyes
- C09B11/245—Phthaleins having both OH and amino substituent(s) on aryl ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zur Herstellung eines chromierbaren Farbstoffes der Triarylmethanreihe. Gegenstand dieses Zusatzpatentes ist ein Verfahren zur Herstellung eines chromier- baren Farbstoffes der Triarylmethanreihe, welches dadurch \gekennzeichnet ist, dass man 1-(4'-Diäthylamino-2'-ogybenzoyl)-o- ogy-carbogy-,2-benzoesäure,
die duroh Ver schmelzen von 5-Ogytrimellitsäureanhydrid mit Diäthylamino-m-phenol während meh- rerer Stunden bei etwa 120-130 C erhält lich ist, mit dem aus diazotiertem 1-Amino- 2-naphthol und Resorcin erhältlichen Azo- farbstoff kondensiert.
<I>Beispiele:</I> 1. 7,4 Gewichtsteile des salzsauren Salzes der Diäthylaminodiogy-carbogy-benzoylben- zoesäure
EMI0001.0023
die durch Verschmelzen von 5-Ogytrimellit- säureanhydrid mit Diäthylamino-m-phenol während mehrerer Stunden bei etwa 120 bis <B>130'</B> C erhältlich ist, werden mit 5,@6 Ge- wiehtsteilen des Azofarbstoffes,
der durch Diazotieren und Kuppeln von 1-Amino-2- naphthol auf R-esorcin erhalten wurde, in 40 Volumteilen konzentrierter Schwefelsäure gelöst und 4-5 Stunden auf<B>90'C</B> erwärmt. Darnach wird in 400 Volumteile Wasser ge gossen, kurz zum Sieden erhitzt, nach Er kalten filtriert, neutral gewaschen und ge trocknet.
Der mit Soda in das Natriumsalz überführte Farbstoff färbt Wolle in grau- -@lanen Tönen und zeigt nachchromiert sehr guteEchtheitseigenschaften.
2. 4,1 Gewichtsteile des salzsauren Salzes der Diäthyla.mino-dioxy-earboxy-benzoyl-ben- zoesäure (Beispiel 1) und 2,8 Gewiehtsteile des Farbstoffes aus diazotiertem 1-Amino-2- naphthol und Resorcin werden zusammen in 80 Gewichtsteilen geschmolzener p-Toluol- sulfosäure gelöst und 5 Stunden auf<B>95'</B> C erwärmt. Es wird heiss in 400 Volumteile Wasser gegossen.
Der Farbstoff wird ab gesaugt, in heisser Sodalösung gelöst und von den letzten Spuren der p Toluolsulfosäure, die als Natriumsalz schwer löslich ist, ab getrennt. Die Lösung wird kongosauer ge stellt, der Farbstoff abgesaugt, neutral ge waschen, getrocknet und mit der berechneten Menge Soda in das leicht lösliche Natrium salz überführt. Aus saurer Lösung liefert der Farbstoff beim Nachohromieren ein Graublau mit guten Eigenschaften.
Verwendet man an Stelle der p-Toluolsulfosäure Methylschwefel- cäure, so erhält man den gleichen Farbstoff.
Process for the preparation of a chromable dye of the triarylmethane series. The subject of this additional patent is a process for the production of a chromable dye of the triarylmethane series, which is characterized in that 1- (4'-diethylamino-2'-ogybenzoyl) -o-ogy-carbogy-, 2-benzoic acid,
which can be obtained by fusing 5-ogytrimellitic anhydride with diethylamino-m-phenol for several hours at about 120-130 C, condenses with the azo dye obtainable from diazotized 1-amino-2-naphthol and resorcinol.
<I> Examples: </I> 1. 7.4 parts by weight of the hydrochloric acid salt of diethylaminodiogy-carbogy-benzoylbenzoic acid
EMI0001.0023
which can be obtained by fusing 5-ogytrimellitic anhydride with diethylamino-m-phenol for several hours at about 120 to 130 ° C are mixed with 5. @ 6 parts by weight of the azo dye
which was obtained by diazotizing and coupling 1-amino-2-naphthol on R-esorcinol, dissolved in 40 parts by volume of concentrated sulfuric acid and heated to 90 ° C for 4-5 hours. Then it is poured into 400 parts by volume of water, heated briefly to the boil, filtered after cold, washed neutral and dried ge.
The dye, which is converted into the sodium salt with soda, dyes wool in gray - @ lan shades and after chrome-plated shows very good fastness properties.
2. 4.1 parts by weight of the hydrochloric acid salt of diethyla.mino-dioxy-earboxy-benzoyl-benzoic acid (Example 1) and 2.8 parts by weight of the dye from diazotized 1-amino-2-naphthol and resorcinol are combined in 80 parts by weight dissolved in molten p-toluenesulfonic acid and heated to <B> 95 '</B> C for 5 hours. It is poured hot into 400 parts by volume of water.
The dye is sucked off, dissolved in hot soda solution and separated from the last traces of p toluenesulfonic acid, which is sparingly soluble as the sodium salt. The solution is acidified to the Congo, the dye is filtered off with suction, washed neutral, dried and converted into the easily soluble sodium salt with the calculated amount of soda. From an acidic solution, the dye produces a gray-blue with good properties when it comes to re-earing.
If methylsulfuric acid is used instead of p-toluenesulfonic acid, the same dye is obtained.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE210831X | 1936-08-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH210831A true CH210831A (en) | 1940-08-15 |
Family
ID=5799439
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH210831D CH210831A (en) | 1936-08-11 | 1937-07-19 | Process for the preparation of a chromable dye of the triarylmethane series. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH210831A (en) |
-
1937
- 1937-07-19 CH CH210831D patent/CH210831A/en unknown
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