CH136391A - Process for the preparation of a polymethine dye. - Google Patents
Process for the preparation of a polymethine dye.Info
- Publication number
- CH136391A CH136391A CH136391DA CH136391A CH 136391 A CH136391 A CH 136391A CH 136391D A CH136391D A CH 136391DA CH 136391 A CH136391 A CH 136391A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- preparation
- formula
- polymethine dye
- violet
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 6
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
- 235000019253 formic acid Nutrition 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine group Chemical group N1=CCC2=CC=CC=C12 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- JNRLEMMIVRBKJE-UHFFFAOYSA-N 4,4'-Methylenebis(N,N-dimethylaniline) Chemical compound C1=CC(N(C)C)=CC=C1CC1=CC=C(N(C)C)C=C1 JNRLEMMIVRBKJE-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000002244 precipitate 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
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
- C09B23/06—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups three >CH- groups, e.g. carbocyanines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
Description
Verfahren zur Herstellung eines Polymethinfarbstoffes. Es wurde gefunden, dass es auf vorteil hafte Weise gelingt, einen Farbstoff der Polymethinreihe herzustellen, wenn man das 1.3.3.7-Tetramethyl-2-methylei.iridolin der Formel
EMI0001.0005
mit Ameisensäure kondensiert.
Das Chlorid des gebildeten 1.1'.3.3 , 3' . 3'. 7. 7'-Oktamethyl-2. 2'-streptomoriovinylen- indocyanins der Formel
EMI0001.0009
bildet getrocknet violette Nadeln, welche sich in Wasser mit rosa Farbe lösen und tannierte Baumwolle in violettnichigen Rosatönen färben.
<I>Beispiel:</I> Zu einer Lösung von 3,74 gr 1. 3 . 3 . 7- Tetramethyl-2-methylenindolin in etwa 50 cm3 Essigsäureanhydrid werden 4 gr Ameisensäure gegeben uiid auf 45 0 erwärmt. Man lässt langsam unter Rühren eine Lösung von 3,74 gr Methylenbase in 50 cm-' Essigsäureanhydrid zutropfen. Die Temperatur wird während 12 Stunden auf etwa 45 0 gehalten.
Nach been digter Reaktion wird mit Wasser zersetzt und zur Lösung Perchlorsäure zugesetzt. Zur Reinigung wird in Eisessig gelöst und die Lösung unter Rühren zur berechneten Menge Natronlauge gegeben, so dass die Farbbase ausfällt. Die Base wird mit Salzsäure dige- riert, wobei zirka 85 % d. Th. an reinem Chlorid des Indoleninrots erhalten werden.
Process for the preparation of a polymethine dye. It has been found that it is possible in an advantageous manner to produce a dye of the polymethine series if the 1.3.3.7-tetramethyl-2-methylei.iridoline of the formula
EMI0001.0005
condensed with formic acid.
The chloride of the formed 1.1'.3.3, 3 '. 3 '. 7. 7'-octamethyl-2. 2'-streptomoriovinylene indocyanines of the formula
EMI0001.0009
when dried forms violet needles, which dissolve in water with a pink color and dye tannic cotton in violet shades of pink.
<I> Example: </I> For a solution of 3.74 gr 1. 3. 3. 7-Tetramethyl-2-methyleneindoline in about 50 cm3 of acetic anhydride are added 4 grams of formic acid and warmed to 45 °. A solution of 3.74 g of methylene base in 50 cm- 'acetic anhydride is slowly added dropwise with stirring. The temperature is held at about 450 for 12 hours.
After the reaction has ended, it is decomposed with water and perchloric acid is added to the solution. For cleaning, it is dissolved in glacial acetic acid and the solution is added to the calculated amount of sodium hydroxide solution while stirring, so that the color base precipitates. The base is digested with hydrochloric acid, about 85% d. Th. Of pure indolenine red chloride.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH136391T | 1928-02-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH136391A true CH136391A (en) | 1929-11-15 |
Family
ID=4394091
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH136391D CH136391A (en) | 1928-02-08 | 1928-02-08 | Process for the preparation of a polymethine dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH136391A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5120858A (en) * | 1991-03-25 | 1992-06-09 | Miles Inc. | Process for the preparation of trimethine dyestuffs |
-
1928
- 1928-02-08 CH CH136391D patent/CH136391A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5120858A (en) * | 1991-03-25 | 1992-06-09 | Miles Inc. | Process for the preparation of trimethine dyestuffs |
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