CH619479A5 - - Google Patents

Download PDF

Info

Publication number: CH619479A5
Authority: CH; Switzerland
Prior art keywords: copper phthalocyanine; reaction mixture; organic solvent; mixture; chlorosulfonic acid
Prior art date: 1975-08-16

Application number

CH1028276A

Other languages

German (de)

English (en)

Inventor

Ronald Dr Barraclough

Robert Langley

Original Assignee

Ciba Geigy 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.)

1975-08-16

Filing date

1976-08-12

Publication date

1980-09-30

1976-08-12 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1980-09-30 Publication of CH619479A5 publication Critical patent/CH619479A5/de

Links

RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical class [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 claims description 36
238000000034 method Methods 0.000 claims description 19
239000003795 chemical substances by application Substances 0.000 claims description 18
239000011541 reaction mixture Substances 0.000 claims description 18
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 claims description 16
XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 16
239000000203 mixture Substances 0.000 claims description 15
239000002904 solvent Substances 0.000 claims description 13
239000003960 organic solvent Substances 0.000 claims description 12
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 12
229910052736 halogen Inorganic materials 0.000 claims description 11
150000002367 halogens Chemical class 0.000 claims description 11
230000002140 halogenating effect Effects 0.000 claims description 8
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
239000003054 catalyst Substances 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
239000000460 chlorine Substances 0.000 claims description 4
239000007858 starting material Substances 0.000 claims description 4
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
229910052740 iodine Inorganic materials 0.000 claims description 3
239000011630 iodine Substances 0.000 claims description 3
239000000049 pigment Substances 0.000 claims description 3
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
238000009835 boiling Methods 0.000 claims description 2
229910052802 copper Inorganic materials 0.000 claims description 2
239000010949 copper Substances 0.000 claims description 2
238000010438 heat treatment Methods 0.000 claims description 2
229930195733 hydrocarbon Natural products 0.000 claims description 2
150000002430 hydrocarbons Chemical class 0.000 claims description 2
229910052742 iron Inorganic materials 0.000 claims description 2
150000002828 nitro derivatives Chemical class 0.000 claims description 2
239000004215 Carbon black (E152) Substances 0.000 claims 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical group Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 1
VVOLVFOSOPJKED-UHFFFAOYSA-N copper phthalocyanine Chemical compound [Cu].N=1C2=NC(C3=CC=CC=C33)=NC3=NC(C3=CC=CC=C33)=NC3=NC(C3=CC=CC=C33)=NC3=NC=1C1=CC=CC=C12 VVOLVFOSOPJKED-UHFFFAOYSA-N 0.000 claims 1
238000002360 preparation method Methods 0.000 claims 1
238000005660 chlorination reaction Methods 0.000 description 13
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 12
125000001309 chloro group Chemical group Cl* 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000000047 product Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
230000026030 halogenation Effects 0.000 description 4
238000005658 halogenation reaction Methods 0.000 description 4
PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
239000012320 chlorinating reagent Substances 0.000 description 3
239000010410 layer Substances 0.000 description 3
230000007935 neutral effect Effects 0.000 description 3
239000012044 organic layer Substances 0.000 description 3
238000001256 steam distillation Methods 0.000 description 3
238000005406 washing Methods 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 2
230000007423 decrease Effects 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
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 2
239000010802 sludge Substances 0.000 description 2
239000000243 solution Substances 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 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
DLKQHBOKULLWDQ-UHFFFAOYSA-N 1-bromonaphthalene Chemical compound C1=CC=C2C(Br)=CC=CC2=C1 DLKQHBOKULLWDQ-UHFFFAOYSA-N 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
241000530268 Lycaena heteronea Species 0.000 description 1
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
239000003513 alkali Substances 0.000 description 1
239000001055 blue pigment Substances 0.000 description 1
230000031709 bromination Effects 0.000 description 1
238000005893 bromination reaction Methods 0.000 description 1
OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000001056 green pigment Substances 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 1
239000007788 liquid Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
YPMOSINXXHVZIL-UHFFFAOYSA-N sulfanylideneantimony Chemical compound [Sb]=S YPMOSINXXHVZIL-UHFFFAOYSA-N 0.000 description 1
238000006277 sulfonation reaction Methods 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 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
- C09B47/10—Obtaining compounds having halogen atoms directly bound to the phthalocyanine skeleton

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

CH1028276A 1975-08-16 1976-08-12 CH619479A5 (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB34196/75A GB1492075A (en)	1975-08-16	1975-08-16	Production of phthalocyanine green

Publications (1)

Publication Number	Publication Date
CH619479A5 true CH619479A5 (fr)	1980-09-30

Family

ID=10362584

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1028276A CH619479A5 (fr)	1975-08-16	1976-08-12

Country Status (7)

Country	Link
US (1)	US4091028A (fr)
JP (1)	JPS5225826A (fr)
CA (1)	CA1049003A (fr)
CH (1)	CH619479A5 (fr)
DE (1)	DE2636487A1 (fr)
FR (1)	FR2321526A1 (fr)
GB (1)	GB1492075A (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS56109253A (en) *	1980-01-31	1981-08-29	Kawasaki Kasei Chem Ltd	Production of highly chlorinated copper phthalocyanine
US4452740A (en) *	1982-07-23	1984-06-05	Basf Wyandotte Corporation	Preparation of chlorinated phthalocyanines
DE3442118A1 (de) *	1984-11-17	1986-05-22	Basf Ag, 6700 Ludwigshafen	Verfahren zur herstellung von farbstarken polyhalogenkupferphthalocyaninen
US4816257A (en) *	1985-09-20	1989-03-28	Research & Education Institute, Harbor-Ucla Medical Center Inc.	Method for producing an in vivo environment suitable for human embryo transfer
CN105733294A (zh) *	2014-12-08	2016-07-06	池州泰阳颜料有限公司	一种酞菁蓝的制备方法
CN108084730B (zh) *	2018-01-02	2020-04-17	滨海康益医药化工有限公司	一种酞菁绿的环保制备方法

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2662085A (en) *	1950-06-29	1953-12-08	Ansbacher Siegle Corp	Process for preparation of chlorinated copper phthalocyanine

1975
- 1975-08-16 GB GB34196/75A patent/GB1492075A/en not_active Expired
1976
- 1976-08-09 US US05/712,577 patent/US4091028A/en not_active Expired - Lifetime
- 1976-08-12 CH CH1028276A patent/CH619479A5/de not_active IP Right Cessation
- 1976-08-13 CA CA76259035A patent/CA1049003A/fr not_active Expired
- 1976-08-13 DE DE19762636487 patent/DE2636487A1/de not_active Withdrawn
- 1976-08-13 FR FR7624735A patent/FR2321526A1/fr active Granted
- 1976-08-16 JP JP51097633A patent/JPS5225826A/ja active Pending

Also Published As

Publication number	Publication date
FR2321526A1 (fr)	1977-03-18
FR2321526B1 (fr)	1978-12-22
DE2636487A1 (de)	1977-02-24
CA1049003A (fr)	1979-02-20
JPS5225826A (en)	1977-02-26
GB1492075A (en)	1977-11-16
US4091028A (en)	1978-05-23

Legal Events

Date	Code	Title	Description
1981-04-30	PL	Patent ceased

Publication	Publication Date	Title
CH619479A5 (fr)	1980-09-30
EP0004635B1 (fr)	1981-08-12	Procédé pour la préparation en continu de l'acide anthranilique
CH688377A5 (de)	1997-08-29	Verfahren zur Herstellung von chlorierten Violanthronen oder Isoviolanthronen.
DE3102200C2 (fr)	1990-10-18
DE2303115C3 (de)	1978-10-26	Verfahren zur Chlorierung der Seitenketten von Toluol, Xylol, Trimethylbenzol und substituierten Produkten dieser Verbindungen
EP0192612B1 (fr)	1988-05-25	Procédé de préparation de chloronitroanilines et de chloronitrophénols
DE3873983T2 (de)	1993-03-11	Verfahren zur herstellung von halogenierten imiden.
CH637417A5 (de)	1983-07-29	Verfahren zur herstellung von hochchloriertem kupferphthalocyanin.
EP0038777B1 (fr)	1983-10-05	Procédé de préparation de dérivés de la quinizarine bisubstitués en position 5 et 8 par de l'hydroxy ou du chlore
EP0157022B1 (fr)	1988-04-27	Procédé pour la préparation d'anhydride chloro-4/bromo-4 naphtalique
EP0250362B1 (fr)	1992-01-02	Procédé de préparation d'un mélange d'amino-1 chloro-2 hydroxy-4 anthraquinone et d'amino-1 bromo-2 hydroxy-4 anthraquinone
CH390271A (de)	1965-04-15	Verfahren zur Herstellung von diarylaminoaromatischen Dicarbonsäuren
DE928344C (de)	1955-05-31	Verfahren zur Durchfuehrung von Chlorierungsreaktionen
EP0508184B1 (fr)	1995-09-27	Procédé de préparation et de purification de la 1-amino-2-phenoxy-4-hydroxyanthraquinone
CH661738A5 (de)	1987-08-14	Verfahren zur herstellung von 6,15-dihydro-5,9,14,18-anthrazintetron und chlorierungsprodukten davon.
EP0134478B1 (fr)	1989-10-04	Procédé de préparation d'un pigment à base de tétrachloro-4,4',7,7' thioindigo
DE2346317C3 (de)	1980-06-19	Verfahren zur Herstellung von Dinitroanthrachinonen
EP0375990B1 (fr)	1994-04-06	Procédé de préparation de la 1-amino-2-bromo-4-hydroxy-anthraquinone
EP0032256B1 (fr)	1983-06-29	Procédé de préparation de phtalocyanines métalliques
DE3643590A1 (de)	1987-07-02	Verfahren zur herstellung von kuepenfarbstoffen aus bromiertem dibenzanthron und 1-aminoanthrachinon
DE2449133C3 (de)	1977-03-24	Verfahren zur Perhalogenierung von Kupferphthalocyanin
DE2705106C3 (de)	1979-07-26	Verfahren zur Herstellung von 2-Amino-3-bromanthrachinon
EP0576995B1 (fr)	1997-09-17	Procédé pour la préparation d'acides 5-halogéno-2-(1-anthraquinonylamino)benzoiques et de 4'-halogéno-2,1(N)-anthraquinonyl-1',2'(N)-benzacridones
DE2258150A1 (de)	1974-05-30	Verfahren zur herstellung von unsubstituiertem isatosaeureanhydrid
DE4014172A1 (de)	1991-11-07	Verfahren zur halogenierung von polycyclischen verbindungen