CH203432A - Process for the preparation of a phthalocyanine series dye. - Google Patents
Process for the preparation of a phthalocyanine series dye.Info
- Publication number
- CH203432A CH203432A CH203432DA CH203432A CH 203432 A CH203432 A CH 203432A CH 203432D A CH203432D A CH 203432DA CH 203432 A CH203432 A CH 203432A
- Authority
- CH
- Switzerland
- Prior art keywords
- dye
- preparation
- phthalocyanine series
- series dye
- thiocresol
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title description 2
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 title 1
- WLHCBQAPPJAULW-UHFFFAOYSA-N 4-methylbenzenethiol Chemical compound CC1=CC=C(S)C=C1 WLHCBQAPPJAULW-UHFFFAOYSA-N 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- LXUNZSDDXMPKLP-UHFFFAOYSA-N 2-Methylbenzenethiol Chemical compound CC1=CC=CC=C1S LXUNZSDDXMPKLP-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 241000530268 Lycaena heteronea Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent 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
- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/08—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Detergent Compositions (AREA)
Description
Verfahren zur Herstellung eines Farbstoffes der Phtbaloeyaninreibe. Es wurdegefunden, dass# man einen neuen wertvollen Farbstoff der Plitaloryaninreihe erhält, wenn man 4 .4'.<B>g".</B> g"-TotTachlor- kupf,erpliäaloeya,nin mit p-Thiokr-esol um setzt.
Man kann das Thiokresol auch in Form seiner Alkalimetallverbindungen verwenden. Mit Vorteil verwendet man Verdünnungs mittel mit.<B>Als,</B> solches kann ein Überschuss des Thiokresolsdienen oder auch Naplithalin, ein AI'kyluaplithalin oder ein aromatischer Nitrokohlenwasiserstoff. Man kann die Um setzung auch un#tererhöhtem Druck ausfüh ren, wobei man als Verdünnungsmittel ter- t.i5,re Basen, wie Pyridin oder Chinolin,
oder aromatische Kohlenwasserstoffe (Benzol, To- luoil, Xylol) benutzt. Man kann dem Um- setzungsgemisell auch geringe Mengen von Metallen, z. B. Kupfer, zusetzen, die den Ha- logenaustaus:ch beschleunigen.
Der neue Farbstoff ist bläuliell grün. Er kann zum Beispiel als Körperfarbstoff ver wendet werden.
<I>Beispiel:</I> <B>5,0</B> Teile 4. 4'.<B>9'.</B> 4"'-Tetraz#hlorkupfer- ph,tli-aloeya,n#in werden mit<B>38,5</B> Teilen p- Thiokresol, <B>17</B> Teilen gemahlenem Kalium- Ily,droxyd, <B>1</B> Teil Kupfermehl und<B>50</B> Teilen Xylol in einem geschlossenen Gefäss<B>-15</B> Ston- den lang auf<B>3,50 ' C</B> erhitzt. Nach dem Ver dünnen mit Xylol wird der Farbstoff ab gesaugt, mit Alkohol gut ausgewaschen, mit verdünüter Salzsäure ausgekocht und neutral gewaschen.
Nach dem Trocknen wird der Farbstoff zur weiteren Reinigung in ider achtfachen Menge Chlorsulfonsäure gelöst, die Lösung in<B>5,0 ' C</B> warmes Wasiser einge gossen, der Farbstoff abgesaugt, neutral ge waschen, Spuren von noch haftender Sä,ure mit Ammoniak entfernt und getrock net. Der Farbstoff ietbläuliehgrüu. In hoch- siedenden Lösungsmitteln ist er etwas lös lich, und zwar mit blaugrüner Farbe.
Process for the preparation of a dye of phtbaloeyanine rub. It has been found that # a new valuable dye of the plitaloryanine series is obtained if one reacts 4 .4 '. <B> g ". </B> g" -TotTachlor- kupf, erpliäaloeya, nin with p-thiocr-esol.
The thiocresol can also be used in the form of its alkali metal compounds. It is advantageous to use diluents with. An excess of thiocresol or naplithalin, an alkyluaplithalin or an aromatic nitrohydrogen can serve as such. The reaction can also be carried out under increased pressure, in which case the diluent used is a basic one such as pyridine or quinoline,
or aromatic hydrocarbons (benzene, toluil, xylene) are used. You can add small amounts of metals, z. B. copper, which accelerate the halogen exchange: ch.
The new dye is bluish green. For example, it can be used as a body pigment.
<I> Example: </I> <B> 5.0 </B> parts 4. 4 '. <B> 9'. </B> 4 "'- Tetraz # hlorkupfer- ph, tli-aloeya, n #in is used with <B> 38.5 </B> parts p-thiocresol, <B> 17 </B> parts ground potassium ily, droxyd, <B> 1 </B> part copper flour and <B> 50 </B> Divide xylene in a closed vessel <B> -15 </B> Stands heated to <B> 3.50 'C </B>. After thinning with xylene, the dye is sucked off, Washed out well with alcohol, boiled with dilute hydrochloric acid and washed neutral.
After drying, the dye is dissolved in eight times the amount of chlorosulfonic acid for further cleaning, the solution is poured into <B> 5.0 'C </B> warm washer, the dye is suctioned off, washed neutral, traces of still adhering seed, ure removed with ammonia and dried. The dye ietbläuliehgüu. It is somewhat soluble in high-boiling solvents, with a blue-green color.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE203432X | 1937-01-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH203432A true CH203432A (en) | 1939-03-15 |
Family
ID=5776402
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH203432D CH203432A (en) | 1937-01-15 | 1937-12-31 | Process for the preparation of a phthalocyanine series dye. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH203432A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2456274A (en) * | 1944-02-14 | 1948-12-14 | Sandoz Ltd | Aryl thio-ethers of metal-containing phthalocyanines and process for producing same |
| US2465089A (en) * | 1946-08-01 | 1949-03-22 | Sandoz Ltd | Sulfonated aryl-thio-ethers of phthalocyanines and process for their manufacture |
-
1937
- 1937-12-31 CH CH203432D patent/CH203432A/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2456274A (en) * | 1944-02-14 | 1948-12-14 | Sandoz Ltd | Aryl thio-ethers of metal-containing phthalocyanines and process for producing same |
| US2465089A (en) * | 1946-08-01 | 1949-03-22 | Sandoz Ltd | Sulfonated aryl-thio-ethers of phthalocyanines and process for their manufacture |
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