CH492763A - Water-insol disazo dyes for vinyl polymers polyamides - Google Patents
Water-insol disazo dyes for vinyl polymers polyamidesInfo
- Publication number
- CH492763A CH492763A CH264668A CH264668A CH492763A CH 492763 A CH492763 A CH 492763A CH 264668 A CH264668 A CH 264668A CH 264668 A CH264668 A CH 264668A CH 492763 A CH492763 A CH 492763A
- Authority
- CH
- Switzerland
- Prior art keywords
- water
- dye
- dichloro
- methoxy
- insoluble
- Prior art date
Links
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 title claims abstract description 9
- 239000004952 Polyamide Substances 0.000 title claims abstract description 4
- 229920002647 polyamide Polymers 0.000 title claims abstract description 4
- 229920002554 vinyl polymer Polymers 0.000 title claims abstract description 4
- 239000000975 dye Substances 0.000 title 1
- IMQLJGSUKJTCMD-UHFFFAOYSA-N n-(2-methoxy-4-methylphenyl)-3-oxobutanamide Chemical compound COC1=CC(C)=CC=C1NC(=O)CC(C)=O IMQLJGSUKJTCMD-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000000049 pigment Substances 0.000 claims abstract description 5
- HUWXDEQWWKGHRV-UHFFFAOYSA-N 3,3'-Dichlorobenzidine Chemical group C1=C(Cl)C(N)=CC=C1C1=CC=C(N)C(Cl)=C1 HUWXDEQWWKGHRV-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000005859 coupling reaction Methods 0.000 claims abstract description 3
- 239000003973 paint Substances 0.000 claims abstract description 3
- 229920000728 polyester Polymers 0.000 claims abstract description 3
- 229920002635 polyurethane Polymers 0.000 claims abstract description 3
- 239000004814 polyurethane Substances 0.000 claims abstract description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 239000000243 solution Substances 0.000 claims description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 4
- 239000000725 suspension Substances 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 229920003023 plastic Polymers 0.000 claims description 3
- 239000004033 plastic Substances 0.000 claims description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 2
- 229960000583 acetic acid Drugs 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 239000007900 aqueous suspension Substances 0.000 claims description 2
- 238000004040 coloring Methods 0.000 claims description 2
- 239000012362 glacial acetic acid Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 239000001632 sodium acetate Substances 0.000 claims description 2
- 235000017281 sodium acetate Nutrition 0.000 claims description 2
- 235000010288 sodium nitrite Nutrition 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 239000001052 yellow pigment Substances 0.000 claims description 2
- 238000004043 dyeing Methods 0.000 claims 1
- 230000008878 coupling Effects 0.000 abstract 1
- 238000010168 coupling process Methods 0.000 abstract 1
- 239000000976 ink Substances 0.000 abstract 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
- C09B35/02—Disazo dyes
- C09B35/039—Disazo dyes characterised by the tetrazo component
- C09B35/08—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl
- C09B35/10—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl from two coupling components of the same type
- C09B35/105—Disazo dyes characterised by the tetrazo component the tetrazo component being a derivative of biphenyl from two coupling components of the same type from two coupling components with reactive methylene groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Water-insol. disazo dye has the formula (I). Dye (I) is prepd. by coupling tetrazotised 3,3'-dichloro-4,4' diaminodiphenyl with 1-acetoacetylamino-2-methoxy-4-methylbenzene. (I) is a water-insoluble pigment with a clear yellow colour. (I) is suitable for use with vinyl polymers super polyamides, polyurethanes, or polyesters, and for use in paints and printing inks.
Description
Verfahren zur Herstellung eines wasserunlöslichen Disazofarbstoffs
Es wurde gefunden, dass man einen wertvollen wasserunlöslichen Disazopigmentfarbstoff erhält, wenn man tetazodertes 3,3'-Dichlor-4,4'-diaminodiphenyl mit 1-Acetoacetylamino-2-methoxy-4-methyl-benzol kuppelt.
Die Umsetzung der Ausgangskomponenten erfolgt bevorzugt in saurer wässriger Lösung oder Suspension bei Temperaturen von -5 bis 200 C.
Der neue Farbstoff entspricht der Formel:
EMI1.1
und stellt ein wasserunlösliches Pigment von klarer gelber Farbe dar. Er eignet sich infolge seiner hohen Farbkraft, seiner ausgezeichneten Lösungsmittelbeständigkeit, seiner hohen Lichtechtheit und seiner hohen Transparenz insbesondere zum Färben von Kunststoffen wie Vinylpolymerisaten, Superpolyamiden, Superpolyurethanen oder Polyestern und für den graphischen Druck sowie für spezielle Gebiete der Lack-, Tapeten- und Papierindustrie.
Beispiel
25,3 g 3,3'-Dichlor < 4,4'aminodliphenyl werden in 1000 g Wasser und 85 ml Salzsäure (20 Bé heiss ge; löst, filtriert und mit Eis auf ca. 0 C abgekiihlt. Dann wirdi mit einer konzentrierten wässrigen Lösung von 14 g Natriumnitrit tetrazotiert.
41 g 1-Acetoacetylamino-2-methoxy-4-methyl-benzol werden in 1000 g Wasser und 25 ml Natronlauge (25 Be) klar gelöst, auf 5-100 C abgekühlt und durch rasches Zugeben von 9 ml Eisessig in feiner Suspen sion ausgefällt. Zu dieser Suspension lässt man die farblose Tetrazotierungslösung in dem Masse zulaufen, wie die Kupplungsreaktion fortschreitet. Der pH-Wert kann dabei durch Zugabe von Natriumacetat vorteilhaft auf 3-7 gehalten werden. Wenn die Realtion be; endet ist, wird auf 40-100 C erhitzt, der so erhaltene gelbe Pigmentfarbstoff abgesaugt und bei 50-60 C getrocknet.
PATENTANSP RÜCHE
I. Verfahren zur Herstellung des wasserunlöslichen Disazofarbstoffs der Formel:
EMI1.2
**WARNUNG** Ende DESC Feld konnte Anfang CLMS uberlappen**.
Process for the preparation of a water-insoluble disazo dye
It has been found that a valuable water-insoluble disazo pigment dye is obtained when tetazoderted 3,3'-dichloro-4,4'-diaminodiphenyl is coupled with 1-acetoacetylamino-2-methoxy-4-methylbenzene.
The starting components are preferably reacted in an acidic aqueous solution or suspension at temperatures from -5 to 200 C.
The new dye corresponds to the formula:
EMI1.1
and is a water-insoluble pigment of clear yellow color. Due to its high color strength, its excellent solvent resistance, its high lightfastness and its high transparency, it is particularly suitable for coloring plastics such as vinyl polymers, super polyamides, super polyurethanes or polyesters and for graphic printing and for special areas of the paint, wallpaper and paper industry.
example
25.3 g of 3,3'-dichloro <4,4'aminodliphenyl are dissolved in 1000 g of water and 85 ml of hydrochloric acid (20 Bé hot;), filtered and cooled to about 0 ° C. with ice. Then, a concentrated aqueous solution is used Solution of 14 g of sodium nitrite tetrazotized.
41 g of 1-acetoacetylamino-2-methoxy-4-methyl-benzene are dissolved in 1000 g of water and 25 ml of sodium hydroxide solution (25 Be), cooled to 5-100 ° C. and precipitated in a fine suspension by quickly adding 9 ml of glacial acetic acid . The colorless tetrazotization solution is allowed to run into this suspension as the coupling reaction progresses. The pH can advantageously be kept at 3-7 by adding sodium acetate. If the Realtion be; ends, the mixture is heated to 40-100 ° C., the yellow pigment dye thus obtained is filtered off with suction and dried at 50-60 ° C.
PATENT APPLICATION
I. Process for the preparation of the water-insoluble disazo dye of the formula:
EMI1.2
** WARNING ** End of DESC field could overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0051891 | 1967-03-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH492763A true CH492763A (en) | 1970-06-30 |
Family
ID=7104994
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH264668A CH492763A (en) | 1967-03-21 | 1968-02-23 | Water-insol disazo dyes for vinyl polymers polyamides |
Country Status (6)
| Country | Link |
|---|---|
| CH (1) | CH492763A (en) |
| DE (1) | DE1644201A1 (en) |
| DK (1) | DK119170B (en) |
| FR (1) | FR1559970A (en) |
| GB (1) | GB1155684A (en) |
| NL (1) | NL6803047A (en) |
-
1967
- 1967-03-21 DE DE19671644201 patent/DE1644201A1/en active Pending
-
1968
- 1968-02-23 CH CH264668A patent/CH492763A/en not_active IP Right Cessation
- 1968-03-04 NL NL6803047A patent/NL6803047A/xx unknown
- 1968-03-05 GB GB1065768A patent/GB1155684A/en not_active Expired
- 1968-03-18 DK DK115068A patent/DK119170B/en unknown
- 1968-03-21 FR FR1559970D patent/FR1559970A/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE1644201A1 (en) | 1970-10-29 |
| FR1559970A (en) | 1969-03-14 |
| DK119170B (en) | 1970-11-23 |
| GB1155684A (en) | 1969-06-18 |
| NL6803047A (en) | 1968-09-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |