CH389128A - Verfahren zur Herstellung triazingruppenhaltiger Farbstoffe - Google Patents

Verfahren zur Herstellung triazingruppenhaltiger Farbstoffe

Info

Publication number: CH389128A
Authority: CH; Switzerland
Prior art keywords: condensed; formula; parts; radical; dyes
Prior art date: 1960-04-11

Application number

CH407760A

Other languages

German (de)

English (en)

Inventor

Karl Dr Ronco

Original Assignee

Ciba Geigy

Priority date (The priority date 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 date listed.)

1960-04-11

Filing date

1960-04-11

Publication date

1965-03-15

1960-04-11 Application filed by Ciba Geigy filed Critical Ciba Geigy

1960-04-11 Priority to CH407760A priority Critical patent/CH389128A/de

1961-03-27 Priority to BE601810A priority patent/BE601810A/fr

1965-03-15 Publication of CH389128A publication Critical patent/CH389128A/de

Links

239000000975 dye Substances 0.000 title claims description 22
238000000034 method Methods 0.000 title claims description 8
238000002360 preparation method Methods 0.000 title claims description 4
JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 title description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 13
125000003277 amino group Chemical group 0.000 claims description 10
-1 triazine radical Chemical class 0.000 claims description 9
MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 claims description 8
UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 8
230000002378 acidificating effect Effects 0.000 claims description 7
239000007859 condensation product Substances 0.000 claims description 6
229910021529 ammonia Inorganic materials 0.000 claims description 5
150000003254 radicals Chemical class 0.000 claims description 5
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
150000005840 aryl radicals Chemical class 0.000 claims description 3
238000009833 condensation Methods 0.000 claims description 3
230000005494 condensation Effects 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 2
239000000987 azo dye Substances 0.000 claims description 2
150000001875 compounds Chemical class 0.000 claims description 2
PPSZHCXTGRHULJ-UHFFFAOYSA-N dioxazine Chemical compound O1ON=CC=C1 PPSZHCXTGRHULJ-UHFFFAOYSA-N 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
150000003141 primary amines Chemical class 0.000 claims description 2
150000003335 secondary amines Chemical class 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 14
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000000203 mixture Substances 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
239000000047 product Substances 0.000 description 4
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
230000008878 coupling Effects 0.000 description 3
238000010168 coupling process Methods 0.000 description 3
238000005859 coupling reaction Methods 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
238000004043 dyeing Methods 0.000 description 2
229940018564 m-phenylenediamine Drugs 0.000 description 2
239000000463 material Substances 0.000 description 2
NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 description 2
235000010288 sodium nitrite Nutrition 0.000 description 2
ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 description 1
BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 1
WBSMIPLNPSCJFS-UHFFFAOYSA-N 5-chloro-2-methoxyaniline Chemical compound COC1=CC=C(Cl)C=C1N WBSMIPLNPSCJFS-UHFFFAOYSA-N 0.000 description 1
GDALETGZDYOOGB-UHFFFAOYSA-N Acridone Natural products C1=C(O)C=C2N(C)C3=CC=CC=C3C(=O)C2=C1O GDALETGZDYOOGB-UHFFFAOYSA-N 0.000 description 1
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
229920000297 Rayon Polymers 0.000 description 1
235000005811 Viola adunca Nutrition 0.000 description 1
240000009038 Viola odorata Species 0.000 description 1
235000013487 Viola odorata Nutrition 0.000 description 1
235000002254 Viola papilionacea Nutrition 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
SMEGJBVQLJJKKX-HOTMZDKISA-N [(2R,3S,4S,5R,6R)-5-acetyloxy-3,4,6-trihydroxyoxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O)OC(=O)C)O)O SMEGJBVQLJJKKX-HOTMZDKISA-N 0.000 description 1
229940081735 acetylcellulose Drugs 0.000 description 1
FZEYVTFCMJSGMP-UHFFFAOYSA-N acridone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3NC2=C1 FZEYVTFCMJSGMP-UHFFFAOYSA-N 0.000 description 1
150000001448 anilines Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
229920002301 cellulose acetate Polymers 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
239000003086 colorant Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
CNXZLZNEIYFZGU-UHFFFAOYSA-N n-(4-amino-2,5-diethoxyphenyl)benzamide Chemical compound C1=C(N)C(OCC)=CC(NC(=O)C=2C=CC=CC=2)=C1OCC CNXZLZNEIYFZGU-UHFFFAOYSA-N 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
239000003973 paint Substances 0.000 description 1
DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical compound C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C4=C2C1=CC=C4C(=O)N1C2=CC=CC=C2N=C13 DGBWPZSGHAXYGK-UHFFFAOYSA-N 0.000 description 1
IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound 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 description 1
239000000049 pigment Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
229920002239 polyacrylonitrile Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
150000003139 primary aliphatic amines Chemical class 0.000 description 1
150000003142 primary aromatic amines Chemical class 0.000 description 1
239000001054 red pigment Substances 0.000 description 1
150000005619 secondary aliphatic amines Chemical class 0.000 description 1
229910000029 sodium carbonate Inorganic materials 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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/12—Preparation of azo dyes from other azo compounds by acylation of amino groups
- C09B43/136—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents
- C09B43/16—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents linking amino-azo or cyanuric acid residues
- 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/04—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Coloring (AREA)

CH407760A 1960-04-11 1960-04-11 Verfahren zur Herstellung triazingruppenhaltiger Farbstoffe CH389128A (de)

Priority Applications (2)

Application Number	Priority Date	Filing Date	Title
CH407760A CH389128A (de)	1960-04-11	1960-04-11	Verfahren zur Herstellung triazingruppenhaltiger Farbstoffe
BE601810A BE601810A (fr)	1960-04-11	1961-03-27	Colorants contenant des groupes de triasine et leur procéde de fabrication

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH407760A CH389128A (de)	1960-04-11	1960-04-11	Verfahren zur Herstellung triazingruppenhaltiger Farbstoffe

Publications (1)

Publication Number	Publication Date
CH389128A true CH389128A (de)	1965-03-15

Family

ID=4269383

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH407760A CH389128A (de)	1960-04-11	1960-04-11	Verfahren zur Herstellung triazingruppenhaltiger Farbstoffe

Country Status (2)

Country	Link
BE (1)	BE601810A (fr)
CH (1)	CH389128A (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE8900256U1 (de) *	1989-01-11	1989-03-23	Hüppe Form Sonnenschutz- und Raumtrennsysteme GmbH, 2900 Oldenburg	Aufzugsvorrichtung eines freihängenden Vorhanges

1960
- 1960-04-11 CH CH407760A patent/CH389128A/de unknown
1961
- 1961-03-27 BE BE601810A patent/BE601810A/fr unknown

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE8900256U1 (de) *	1989-01-11	1989-03-23	Hüppe Form Sonnenschutz- und Raumtrennsysteme GmbH, 2900 Oldenburg	Aufzugsvorrichtung eines freihängenden Vorhanges

Also Published As

Publication number	Publication date
BE601810A (fr)	1961-07-17

Publication	Publication Date	Title
DE1148341B (de)	1963-05-09	Verfahren zur Herstellung von Farbstoffen
DE2243999A1 (de)	1973-03-15	Neue disazopigmente, verfahren zu deren herstellung und verwendung
DE2243955A1 (de)	1973-03-15	Neue disazopigmente und verfahren zu deren herstellung und verwendung
DE1142212B (de)	1963-01-10	Verfahren zur Herstellung von sulfonsaeuregruppenfreien Dioxazinfarbstoffen
DE2134896A1 (de)	1973-02-01	Verfahren zur herstellung von cyangruppenhaltigen azofarbstoffen
CH389128A (de)	1965-03-15	Verfahren zur Herstellung triazingruppenhaltiger Farbstoffe
DE2410240A1 (de)	1974-09-12	Disazopigmente, verfahren zu deren herstellung und verwendung
US2554443A (en)	1951-05-22	Azo safranine leather dyestuffs
DE1644127A1 (de)	1971-04-15	Verfahren zur Herstellung von Disazopigmenten
DE2002067A1 (de)	1970-08-27	Neue Disazopigmente und Verfahren zu deren Herstellung
DE845083C (de)	1952-07-28	Verfahren zur Herstellung wasserunloeslicher Azofarbstoffe
DE1444729A1 (de)	1969-05-14	Verfahren zur Herstellung von neuen Azopigmentfarbstoffen
DE598327C (de)	1934-06-08	Verfahren zur Herstellung von Kuepenfarbstoffen
DE2025429A1 (en)	1971-12-09	Bis-azomethine pigment dyes - giving yellow to red shades of good - fastness esp to light and solvents
US2054397A (en)	1936-09-15	Azodyestuffs and intermediate
US2628231A (en)	1953-02-10	Azo compounds of the anthraquinone series
CH347917A (de)	1960-07-31	Verfahren zur Herstellung neuer Carbonsäureamidgruppen enthaltender Azofarbstoffe
DE941381C (de)	1956-04-12	Verfahren zur Herstellung von Kuepenfarbstoffen
CH493606A (de)	1970-07-15	Verfahren zur Herstellung basischer Farbstoffe
US1840383A (en)	1932-01-12	Vat dyestuffs of the anthraquinone acridone series
DE2365361A1 (de)	1974-08-15	Triazinylverbindungen, ihre herstellung und verwendung
DE1719067A1 (de)	1971-08-12	Neue Monoazofarbstoffpigmente und Verfahren zu deren Herstellung
CH343044A (de)	1959-12-15	Verfahren zur Herstellung von Azopigmenten
CH472473A (de)	1969-05-15	Verfahren zur Herstellung neuer Monoazofarbstoffpigmente
CH305009A (de)	1955-01-31	Verfahren zur Herstellung eines Azopigmentes.

CH389128A - Verfahren zur Herstellung triazingruppenhaltiger Farbstoffe - Google Patents

Info

Links

Classifications

Landscapes

Priority Applications (2)

Applications Claiming Priority (1)

Publications (1)

Family

ID=4269383

Family Applications (1)

Country Status (2)

Cited By (1)

Cited By (1)

Also Published As

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