CH390433A - Verfahren zur Herstellung basischer Farbstoffe der Perylenreihe - Google Patents

Verfahren zur Herstellung basischer Farbstoffe der Perylenreihe

Info

Publication number: CH390433A
Authority: CH; Switzerland
Prior art keywords: parts; mixture; perylene; water; dye
Prior art date: 1959-08-13

Application number

CH708560A

Other languages

German (de)

English (en)

Inventor

Arnold Dr Tartter

Werner Dr Bolzau

Original Assignee

Basf Ag

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.)

1959-08-13

Filing date

1960-06-22

Publication date

1965-04-15

1960-06-22 Application filed by Basf Ag filed Critical Basf Ag

1965-04-15 Publication of CH390433A publication Critical patent/CH390433A/de

Links

238000000034 method Methods 0.000 title claims description 8
239000000981 basic dye Substances 0.000 title claims description 5
238000002360 preparation method Methods 0.000 title claims description 4
125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 title description 4
239000000975 dye Substances 0.000 claims description 17
239000002253 acid Substances 0.000 claims description 12
150000001875 compounds Chemical class 0.000 claims description 7
FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical class C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 4
125000003710 aryl alkyl group Chemical group 0.000 claims description 4
229910052757 nitrogen Inorganic materials 0.000 claims description 3
125000002947 alkylene group Chemical group 0.000 claims description 2
125000000623 heterocyclic group Chemical group 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
150000003949 imides Chemical class 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 claims description 2
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 21
239000000203 mixture Substances 0.000 description 19
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
CLYVDMAATCIVBF-UHFFFAOYSA-N pigment red 224 Chemical compound C=12C3=CC=C(C(OC4=O)=O)C2=C4C=CC=1C1=CC=C2C(=O)OC(=O)C4=CC=C3C1=C42 CLYVDMAATCIVBF-UHFFFAOYSA-N 0.000 description 9
150000007513 acids Chemical class 0.000 description 8
235000019445 benzyl alcohol Nutrition 0.000 description 7
239000000463 material Substances 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
239000001044 red dye Substances 0.000 description 6
-1 alkaline earth metal salts Chemical class 0.000 description 5
150000001412 amines Chemical class 0.000 description 5
238000009835 boiling Methods 0.000 description 5
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 5
BKFWZZRDUKASOU-UHFFFAOYSA-N 2-n-cyclohexylpropane-1,2-diamine Chemical compound NCC(C)NC1CCCCC1 BKFWZZRDUKASOU-UHFFFAOYSA-N 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 4
238000003756 stirring Methods 0.000 description 4
RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 3
JNFLSJUGIONDMJ-UHFFFAOYSA-N 2-n,2-n-diethylpropane-1,2-diamine Chemical compound CCN(CC)C(C)CN JNFLSJUGIONDMJ-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
238000001816 cooling Methods 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
239000000243 solution Substances 0.000 description 3
CUTAORBVSQRYEF-UHFFFAOYSA-N 5,6-dichloroperylene-1,2,3,4-tetracarboxylic acid Chemical compound C1=CC(C2=C(C(C(=O)O)=C(C(O)=O)C=3C2=C2C(Cl)=C(Cl)C=3C(O)=O)C(O)=O)=C3C2=CC=CC3=C1 CUTAORBVSQRYEF-UHFFFAOYSA-N 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
239000010985 leather Substances 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
WSRHMJYUEZHUCM-UHFFFAOYSA-N perylene-1,2,3,4-tetracarboxylic acid Chemical class C=12C3=CC=CC2=CC=CC=1C1=C(C(O)=O)C(C(O)=O)=C(C(O)=O)C2=C1C3=CC=C2C(=O)O WSRHMJYUEZHUCM-UHFFFAOYSA-N 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
YGRXZLAMYLGXMF-UHFFFAOYSA-N sbb059221 Chemical compound C1=C(Cl)C(C=2C(Cl)=CC=3C(OC(=O)C=4C=3C=2C2=C(Cl)C=4)=O)=C3C2=C(Cl)C=C2C(=O)OC(=O)C1=C32 YGRXZLAMYLGXMF-UHFFFAOYSA-N 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
IULLPVRLBFJTKD-UHFFFAOYSA-N 1-n-(2-methylpropyl)propane-1,2-diamine Chemical compound CC(C)CNCC(C)N IULLPVRLBFJTKD-UHFFFAOYSA-N 0.000 description 1
VLMRJJXAISWQFH-UHFFFAOYSA-N 2-n-(2-methylpropyl)propane-1,2-diamine Chemical compound CC(C)CNC(C)CN VLMRJJXAISWQFH-UHFFFAOYSA-N 0.000 description 1
JKRLDNPTLLLNFZ-UHFFFAOYSA-N 2-n-(2-phenylethyl)propane-1,2-diamine Chemical compound NCC(C)NCCC1=CC=CC=C1 JKRLDNPTLLLNFZ-UHFFFAOYSA-N 0.000 description 1
CYDDCGURYVWSDZ-UHFFFAOYSA-N 2-n-propan-2-ylpropane-1,2-diamine Chemical compound CC(C)NC(C)CN CYDDCGURYVWSDZ-UHFFFAOYSA-N 0.000 description 1
FXTRRLIESPAUHT-UHFFFAOYSA-N 3-(azepan-1-yl)propan-1-amine Chemical compound NCCCN1CCCCCC1 FXTRRLIESPAUHT-UHFFFAOYSA-N 0.000 description 1
VPBWZBGZWHDNKL-UHFFFAOYSA-N 3-pyrrolidin-1-ylpropan-1-amine Chemical compound NCCCN1CCCC1 VPBWZBGZWHDNKL-UHFFFAOYSA-N 0.000 description 1
BLSYYIYOPBPOLG-UHFFFAOYSA-N 5,6,7,8-tetrachloroperylene-1,2,3,4-tetracarboxylic acid Chemical compound C1=CC(C2=C(C(C(=O)O)=C(C(O)=O)C=3C2=C2C(Cl)=C(Cl)C=3C(O)=O)C(O)=O)=C3C2=C(Cl)C(Cl)=CC3=C1 BLSYYIYOPBPOLG-UHFFFAOYSA-N 0.000 description 1
OEEDCRIROHCGAM-UHFFFAOYSA-N C(CCCCC(C)C)NC(CN)C Chemical compound C(CCCCC(C)C)NC(CN)C OEEDCRIROHCGAM-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
ZNUNZCHOKKVGJM-UHFFFAOYSA-N N.C=12C3=CC=CC2=CC=CC=1C1=C(C(O)=O)C(C(O)=O)=C(C(O)=O)C2=C1C3=CC=C2C(=O)O Chemical compound N.C=12C3=CC=CC2=CC=CC=1C1=C(C(O)=O)C(C(O)=O)=C(C(O)=O)C2=C1C3=CC=C2C(=O)O ZNUNZCHOKKVGJM-UHFFFAOYSA-N 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
239000003513 alkali Substances 0.000 description 1
125000005263 alkylenediamine group Chemical group 0.000 description 1
150000001491 aromatic compounds Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
239000003086 colorant Substances 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000004043 dyeing Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
238000001914 filtration Methods 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 description 1
ITZPOSYADVYECJ-UHFFFAOYSA-N n'-cyclohexylpropane-1,3-diamine Chemical compound NCCCNC1CCCCC1 ITZPOSYADVYECJ-UHFFFAOYSA-N 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
150000000000 tetracarboxylic acids Chemical class 0.000 description 1
239000000984 vat dye 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
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/62—Cyclic imides or amidines of peri-dicarboxylic acids of the anthracene, benzanthrene, or perylene series
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/16—Writing inks
- C09D11/18—Writing inks specially adapted for ball-point writing instruments

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Wood Science & Technology (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Coloring (AREA)
Inks, Pencil-Leads, Or Crayons (AREA)

CH708560A 1959-08-13 1960-06-22 Verfahren zur Herstellung basischer Farbstoffe der Perylenreihe CH390433A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DEB54408A DE1117246B (de)	1959-08-13	1959-08-13	Verfahren zur Herstellung basischer Farbstoffe der Perylenreihe

Publications (1)

Publication Number	Publication Date
CH390433A true CH390433A (de)	1965-04-15

Family

ID=6970588

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH708560A CH390433A (de)	1959-08-13	1960-06-22	Verfahren zur Herstellung basischer Farbstoffe der Perylenreihe

Country Status (4)

Country	Link
BE (1)	BE593932A (fr)
CH (1)	CH390433A (fr)
DE (1)	DE1117246B (fr)
GB (1)	GB894859A (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3240783A (en) *	1963-01-18	1966-03-15	Eastman Kodak Co	Cyanomethylidene quinolines
US4762569A (en) *	1987-08-07	1988-08-09	Sanyo Color Works, Ltd.	Easily dispersible pigment composition and dispersing method
DE19709798A1 (de) *	1997-03-10	1998-09-17	Clariant Gmbh	Pigmentzubereitungen und Verfahren zu ihrer Herstellung

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2668815A (en) *	1951-05-24	1954-02-09	Gen Aniline & Film Corp	Vat dyestuffs of the perylenetetracarboxylic acid bis-arylimide series

1959
- 1959-08-13 DE DEB54408A patent/DE1117246B/de active Pending
1960
- 1960-06-22 CH CH708560A patent/CH390433A/de unknown
- 1960-08-09 BE BE593932A patent/BE593932A/fr unknown
- 1960-08-12 GB GB27933/60A patent/GB894859A/en not_active Expired

Also Published As

Publication number	Publication date
GB894859A (en)	1962-04-26
BE593932A (fr)	1961-02-09
DE1117246B (de)	1961-11-16

Publication	Publication Date	Title
DE1644306B2 (de)	1976-05-06	Basische anthrachinon- und nitrofarbstoffe und verfahren zu deren herstellung
CH390433A (de)	1965-04-15	Verfahren zur Herstellung basischer Farbstoffe der Perylenreihe
DE3025557A1 (de)	1982-02-04	Loesung kationischer polyazofarbstoffe
DE1094897B (de)	1960-12-15	Verfahren zur Herstellung eines Pigmentfarbstoffs
DE742326C (de)	1943-12-13	Verfahren zur Herstellung von Kuepenfarbstoffen der Fluoranthenreihe
DE655590C (de)	1938-01-19	Verfahren zur Herstellung von Azofarbstoffen
DE3017935C2 (de)	1986-11-27	1,1'-Binaphthyl-4,4',5,5',8,8'-hexacarbonsäurederivate
DE86223C (fr)
DE935566C (de)	1955-11-24	Verfahren zur Herstellung von Kuepenfarbstoffen
DE894245C (de)	1953-10-22	Verfahren zur Herstellung von wasserloeslichen Salzen der 1, 4-Diamino-benzolsulfonsaeure-N, deren Aminogruppe in der 1-Stellung des Benzol-kerns durch einen Kohlenwasserstoffrest substituiert ist
DE663853C (de)	1938-08-15	Verfahren zur Herstellung von Aminen von Verbindungen vom allgemeinen Aufbau
DE1132272B (de)	1962-06-28	Verfahren zur Herstellung eines Pigmentfarbstoffs
DE102362C (fr)
AT217160B (de)	1961-09-11	Mittel zum Färben von menschlichen Haaren
AT159419B (de)	1940-08-26	Verfahren zur Herstellung metallhaltiger Farbstoffe.
DE723822C (de)	1942-08-11	Verfahren zur Herstellung von N-substituierten Abkoemmlingen von 1, 4-Diaminoanthrachinonen
DE1544580C (de)	1971-02-18	Verfahren zur Herstellung wasserlos hcher chromhaltiger Farbstoffe
DE360530C (de)	1922-10-03	Verfahren zur Einfuehrung von Arylaminogruppen in Aminoanthrachinone
DE3115548A1 (de)	1982-11-11	Verfahren zur herstellung von 1-alkylaminoanthrachinonen
DE504240C (de)	1930-08-01	Verfahren zur Darstellung von Abkoemmlingen des Pyrazolanthrons
DE846593C (de)	1952-08-14	Verfahren zur Herstellung von Kuepenfarbstoffen
DE1794127A1 (de)	1971-11-18	Neue Pigmentfarbstoffe
DE1149477B (de)	1963-05-30	Verfahren zur Herstellung von Fluorubin oder dessen Substitutionsprodukten
DE950949C (de)	1956-10-18	Verfahren zur Herstellung von Anthrachinonfarbstoffen
DE1272475B (de)	1968-07-11	Verfahren zur Herstellung von Azopigmenten