CH391156A - Verfahren zur Herstellung von Farbstoffen der Azaporphinreihe - Google Patents

Verfahren zur Herstellung von Farbstoffen der Azaporphinreihe

Info

Publication number: CH391156A
Authority: CH; Switzerland
Prior art keywords: dyes; parts; amine; azaporphin; radical
Prior art date: 1958-05-10

Application number

CH7259059A

Other languages

German (de)

English (en)

Inventor

Arnold Dr Tartter

Alfred Dr Schoellig

Hans Dr Otterbach

Otto Dr Stichnoth

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.)

1958-05-10

Filing date

1959-04-27

Publication date

1965-04-30

1959-04-27 Application filed by Basf Ag filed Critical Basf Ag

1965-04-30 Publication of CH391156A publication Critical patent/CH391156A/de

Links

239000000975 dye Substances 0.000 title claims description 25
238000000034 method Methods 0.000 title claims description 7
238000004519 manufacturing process Methods 0.000 title claims description 4
150000001412 amines Chemical class 0.000 claims description 10
238000004043 dyeing Methods 0.000 claims description 6
239000002253 acid Substances 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 5
150000001805 chlorine compounds Chemical class 0.000 claims description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
229910052757 nitrogen Inorganic materials 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
239000000835 fiber Substances 0.000 claims 1
239000000126 substance Substances 0.000 claims 1
239000004753 textile Substances 0.000 claims 1
-1 alkylene radical Chemical group 0.000 description 16
238000003756 stirring Methods 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
239000001099 ammonium carbonate Substances 0.000 description 7
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 6
RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
150000001298 alcohols Chemical class 0.000 description 5
235000012501 ammonium carbonate Nutrition 0.000 description 5
125000004432 carbon atom Chemical group C* 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 4
229910052802 copper Inorganic materials 0.000 description 4
239000010949 copper Substances 0.000 description 4
150000002334 glycols Chemical class 0.000 description 4
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
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 4
150000003254 radicals Chemical class 0.000 description 4
239000000243 solution Substances 0.000 description 4
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
125000001033 ether group Chemical group 0.000 description 3
239000005457 ice water Substances 0.000 description 3
239000000463 material Substances 0.000 description 3
239000000203 mixture Substances 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
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 2
HXDLWJWIAHWIKI-UHFFFAOYSA-N 2-hydroxyethyl acetate Chemical compound CC(=O)OCCO HXDLWJWIAHWIKI-UHFFFAOYSA-N 0.000 description 2
REJGIEGOYWEWPR-UHFFFAOYSA-N 3-(2-methylpropoxy)propan-1-amine Chemical compound CC(C)COCCCN REJGIEGOYWEWPR-UHFFFAOYSA-N 0.000 description 2
NZMUWHNIWFMBNW-UHFFFAOYSA-N 3-(3-methylbutoxy)propan-1-amine Chemical compound CC(C)CCOCCCN NZMUWHNIWFMBNW-UHFFFAOYSA-N 0.000 description 2
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
RISUMPVKPHEEJG-UHFFFAOYSA-N C1=CC=CC=C1[Cu](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 Chemical compound C1=CC=CC=C1[Cu](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 RISUMPVKPHEEJG-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
229910052782 aluminium Inorganic materials 0.000 description 2
235000012538 ammonium bicarbonate Nutrition 0.000 description 2
150000005840 aryl radicals Chemical class 0.000 description 2
239000001045 blue dye Substances 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
238000009833 condensation Methods 0.000 description 2
125000005842 heteroatom Chemical group 0.000 description 2
229910052742 iron Inorganic materials 0.000 description 2
229910052759 nickel Inorganic materials 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
239000000843 powder Substances 0.000 description 2
GJAWHXHKYYXBSV-UHFFFAOYSA-N quinolinic acid Chemical compound OC(=O)C1=CC=CN=C1C(O)=O GJAWHXHKYYXBSV-UHFFFAOYSA-N 0.000 description 2
239000002904 solvent Substances 0.000 description 2
RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
GDELFUQKNPLION-UHFFFAOYSA-N 4-ethoxybutan-1-amine Chemical compound CCOCCCCN GDELFUQKNPLION-UHFFFAOYSA-N 0.000 description 1
WNKQDGLSQUASME-UHFFFAOYSA-N 4-sulfophthalic acid Chemical compound OC(=O)C1=CC=C(S(O)(=O)=O)C=C1C(O)=O WNKQDGLSQUASME-UHFFFAOYSA-N 0.000 description 1
229910000013 Ammonium bicarbonate Inorganic materials 0.000 description 1
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
229920002160 Celluloid Polymers 0.000 description 1
SZZYLYUVTJLJQM-UHFFFAOYSA-J Cl[Cu](Cl)(Cl)Cl Chemical compound Cl[Cu](Cl)(Cl)Cl SZZYLYUVTJLJQM-UHFFFAOYSA-J 0.000 description 1
239000000020 Nitrocellulose Substances 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical class NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
238000007605 air drying Methods 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
238000005576 amination reaction Methods 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000001491 aromatic compounds Chemical class 0.000 description 1
AKGGYBADQZYZPD-UHFFFAOYSA-N benzyl acetone Natural products CC(=O)CCC1=CC=CC=C1 AKGGYBADQZYZPD-UHFFFAOYSA-N 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
229920003086 cellulose ether Polymers 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000004040 coloring Methods 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
150000004292 cyclic ethers Chemical group 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 1
238000001035 drying Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
239000011888 foil Substances 0.000 description 1
238000000227 grinding Methods 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
125000002768 hydroxyalkyl group Chemical group 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
239000000025 natural resin Substances 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229920001220 nitrocellulos Polymers 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000009965 odorless effect Effects 0.000 description 1
238000000643 oven drying Methods 0.000 description 1
239000005022 packaging material Substances 0.000 description 1
239000003973 paint Substances 0.000 description 1
238000010422 painting Methods 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 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
229920001225 polyester resin Polymers 0.000 description 1
239000004645 polyester resin Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
239000000057 synthetic resin Substances 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
239000008096 xylene 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
- C09B47/24—Obtaining compounds having —COOH or —SO3H radicals, or derivatives thereof, directly bound to the phthalocyanine radical
- C09B47/26—Amide radicals

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Coloring (AREA)
Inks, Pencil-Leads, Or Crayons (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

CH7259059A 1958-05-10 1959-04-27 Verfahren zur Herstellung von Farbstoffen der Azaporphinreihe CH391156A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DEB48869A DE1203404B (de)	1958-05-10	1958-05-10	Verfahren zur Herstellung von in organischen Mitteln loeslichen Farbstoffen der Tetrazaporphinreihe

Publications (1)

Publication Number	Publication Date
CH391156A true CH391156A (de)	1965-04-30

Family

ID=6968708

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH7259059A CH391156A (de)	1958-05-10	1959-04-27	Verfahren zur Herstellung von Farbstoffen der Azaporphinreihe

Country Status (4)

Country	Link
BE (1)	BE578359A (fr)
CH (1)	CH391156A (fr)
DE (1)	DE1203404B (fr)
NL (2)	NL122488C (fr)

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE696591C (de) *	1937-05-26	1940-09-25	I G Farbenindustrie Akt Ges	Verfahren zur Herstellung von Farbstoffen
DE1094898B (de)	1957-03-18	1960-12-15	Ciba Geigy	Verfahren zur Herstellung acetonloeslicher Phthalocyaninfarbstoffe

1958
- 1958-05-10 DE DEB48869A patent/DE1203404B/de active Pending
1959
- 1959-04-27 CH CH7259059A patent/CH391156A/de unknown
- 1959-05-04 BE BE578359A patent/BE578359A/fr unknown
- 1959-05-05 NL NL238909A patent/NL122488C/xx active
- 1959-05-05 NL NL238909D patent/NL238909A/xx unknown

Also Published As

Publication number	Publication date
DE1203404B (de)	1965-10-21
NL238909A (fr)	1964-01-27
BE578359A (fr)	1959-08-31
NL122488C (fr)	1967-05-17

Publication	Publication Date	Title
DE1148341B (de)	1963-05-09	Verfahren zur Herstellung von Farbstoffen
CH481998A (de)	1969-11-30	Verfahren zur Herstellung reaktiver, schwermetallhaltiger Formazanfarbstoffe
EP0231837B1 (fr)	1989-08-02	Procédé de préparation de colorants phtalocyanine solubles dans l'eau
EP0691383A1 (fr)	1996-01-10	Colorants azoiques ayant des groupes réactifs avec les fibres
JPH06184460A (ja)	1994-07-05	溶媒可溶性染料の水性組成物
DE1569727A1 (de)	1970-05-14	Verfahren zur Herstellung von Farbstoffen
CH391156A (de)	1965-04-30	Verfahren zur Herstellung von Farbstoffen der Azaporphinreihe
DE1959308A1 (de)	1971-06-03	Farbstoffsalze der Phthaloxyaninreihe
DE2008811C3 (de)	1974-06-27	Reaktivfarbstoffe
DE2404069C2 (fr)	1987-05-27
DE2729915A1 (de)	1978-01-19	Gemische von 1 zu 2-kobaltkomplexazoverbindungen, deren herstellung und verwendung
DE1283997B (de)	1968-11-28	Verfahren zur Herstellung wasserloeslicher Phthalocyaninfarbstoffe
DE1293365B (de)	1969-04-24	Verfahren zur Herstellung von Phthalocyaninfarbstoffen
CH688689A5 (de)	1998-01-15	Loesungsmittelfarbstoffe.
DE60114562T2 (de)	2006-05-24	Neue farbstoffe, stabilisatoren für farbstoffe, tintenzusammensetzungen und herstellungsverfahren dafür
DE1049996B (de)	1959-02-05	Verfahren zur Herstellung basischer Farbstoffe der Phthalocyaninreihe
EP0018008A2 (fr)	1980-10-29	Procédé de production du tétrachloro-4,4',7,7' thio-indigo sous forme de pigments lasurants
EP0043003B1 (fr)	1983-09-07	Procédé pour la préparation de colorants anioniques de la série des quinophtalones
DE1569727C (de)	1972-11-16	Verfahren zur Herstellung von Phthalocyaninfarbstoffen
DE1278042B (de)	1968-09-19	Verfahren zur Herstellung von kationischen Farbstoffen
EP0073965B1 (fr)	1984-10-10	Colorants du type phtalocyanine, leur préparation et leur utilisation
CH413180A (de)	1966-05-15	Verfahren zur Herstellung neuer organischer Farbstoffe
DE2439983C3 (de)	1977-07-14	Verfahren zur Herstellung von leicht dispergierbaren Phthalocyaninpigmenten der beta-modifikation und deren Verwendung
DE2816983A1 (de)	1978-11-02	Stabile, fluessige, hochkonzentrierte farbstoffzubereitungen, ihre herstellung und verwendung
DE380712C (de)	1923-09-10	Verfahren zur Herstellung von Kuepenfarbstoffen und Ausgangsstoffen dafuer