CH386029A - Verfahren zur Herstellung von Pigmentfarbstoffen - Google Patents

Verfahren zur Herstellung von Pigmentfarbstoffen

Info

Publication number: CH386029A
Authority: CH; Switzerland
Prior art keywords: acid; cyclization; carried out; formula; compounds
Prior art date: 1960-12-06

Application number

CH1365960A

Other languages

German (de)

English (en)

Inventor

Bohler Hans

Fritz Dr Kehrer

Original Assignee

Sandoz 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.)

1960-12-06

Filing date

1960-12-06

Publication date

1964-12-31

1960-12-06 Application filed by Sandoz Ag filed Critical Sandoz Ag

1960-12-06 Priority to CH1365960A priority Critical patent/CH386029A/de

1961-01-06 Priority to CH18161A priority patent/CH422200A/de

1961-11-03 Priority to BE609925A priority patent/BE609925A/fr

1964-12-31 Publication of CH386029A publication Critical patent/CH386029A/de

Links

238000000034 method Methods 0.000 title claims description 7
239000000049 pigment Substances 0.000 title claims description 5
239000000975 dye Substances 0.000 title claims description 4
238000004519 manufacturing process Methods 0.000 title description 2
-1 2,5-di- (4'-chlorophenoxy) -terephthalic acid Chemical compound 0.000 claims description 10
238000004043 dyeing Methods 0.000 claims description 8
238000009833 condensation Methods 0.000 claims description 6
230000005494 condensation Effects 0.000 claims description 6
239000003795 chemical substances by application Substances 0.000 claims description 5
150000001875 compounds Chemical class 0.000 claims description 5
239000004753 textile Substances 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 3
239000004215 Carbon black (E152) Substances 0.000 claims description 2
230000002378 acidificating effect Effects 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims description 2
229930195733 hydrocarbon Natural products 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
239000000155 melt Substances 0.000 claims description 2
239000003960 organic solvent Substances 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
238000007363 ring formation reaction Methods 0.000 claims 3
230000001419 dependent effect Effects 0.000 claims 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
239000000463 material Substances 0.000 claims 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
229920000297 Rayon Polymers 0.000 description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
239000002904 solvent Substances 0.000 description 4
DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
229920000137 polyphosphoric acid Polymers 0.000 description 3
229920000915 polyvinyl chloride Polymers 0.000 description 3
239000004800 polyvinyl chloride Substances 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
229920003002 synthetic resin Polymers 0.000 description 3
239000000057 synthetic resin Substances 0.000 description 3
UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
229920002955 Art silk Polymers 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
ZCWFTAOZCMHXPU-UHFFFAOYSA-N OC(C(C=C(C(C(O)=O)=C1)OC2=CC=CC=C2)=C1OC1=CC=CC=C1)=O Chemical compound OC(C(C=C(C(C(O)=O)=C1)OC2=CC=CC=C2)=C1OC1=CC=CC=C1)=O ZCWFTAOZCMHXPU-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
239000002253 acid Substances 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
238000010790 dilution Methods 0.000 description 2
239000012895 dilution Substances 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
239000000243 solution Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
239000002966 varnish 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
YQCMKAVTVONKPD-UHFFFAOYSA-N 1,2-dichloroxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=C(Cl)C(Cl)=CC=C3OC2=C1 YQCMKAVTVONKPD-UHFFFAOYSA-N 0.000 description 1
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 1
JTPNRXUCIXHOKM-UHFFFAOYSA-N 1-chloronaphthalene Chemical compound C1=CC=C2C(Cl)=CC=CC2=C1 JTPNRXUCIXHOKM-UHFFFAOYSA-N 0.000 description 1
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
229920002292 Nylon 6 Polymers 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
239000004743 Polypropylene Substances 0.000 description 1
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
229920004933 Terylene® Polymers 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
125000002252 acyl group Chemical group 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
239000003513 alkali Substances 0.000 description 1
125000003282 alkyl amino group Chemical group 0.000 description 1
125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
150000004056 anthraquinones Chemical class 0.000 description 1
125000001769 aryl amino group Chemical group 0.000 description 1
125000004391 aryl sulfonyl group Chemical group 0.000 description 1
125000004104 aryloxy group Chemical group 0.000 description 1
238000004061 bleaching Methods 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
150000001733 carboxylic acid esters Chemical class 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002301 cellulose acetate Polymers 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
229940106681 chloroacetic acid Drugs 0.000 description 1
XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
238000004040 coloring Methods 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
238000005108 dry cleaning Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
230000004907 flux Effects 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000000976 ink Substances 0.000 description 1
OHZZTXYKLXZFSZ-UHFFFAOYSA-I manganese(3+) 5,10,15-tris(1-methylpyridin-1-ium-4-yl)-20-(1-methylpyridin-4-ylidene)porphyrin-22-ide pentachloride Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Mn+3].C1=CN(C)C=CC1=C1C(C=C2)=NC2=C(C=2C=C[N+](C)=CC=2)C([N-]2)=CC=C2C(C=2C=C[N+](C)=CC=2)=C(C=C2)N=C2C(C=2C=C[N+](C)=CC=2)=C2N=C1C=C2 OHZZTXYKLXZFSZ-UHFFFAOYSA-I 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
230000005012 migration Effects 0.000 description 1
238000013508 migration Methods 0.000 description 1
239000000203 mixture Substances 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
239000001053 orange pigment Substances 0.000 description 1
239000003973 paint Substances 0.000 description 1
238000010422 painting Methods 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
239000003495 polar organic solvent Substances 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
239000005020 polyethylene terephthalate Substances 0.000 description 1
229920001155 polypropylene Polymers 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
239000000047 product Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000001054 red pigment Substances 0.000 description 1
238000001226 reprecipitation Methods 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
238000009987 spinning Methods 0.000 description 1
125000002130 sulfonic acid ester group Chemical group 0.000 description 1
150000003504 terephthalic acids Chemical class 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
125000004950 trifluoroalkyl group Chemical group 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000001052 yellow pigment Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0041—Optical brightening agents, organic pigments
- 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
- C09B57/00—Other synthetic dyes of known constitution

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Coloring (AREA)

CH1365960A 1960-12-06 1960-12-06 Verfahren zur Herstellung von Pigmentfarbstoffen CH386029A (de)

Priority Applications (3)

Application Number	Priority Date	Filing Date	Title
CH1365960A CH386029A (de)	1960-12-06	1960-12-06	Verfahren zur Herstellung von Pigmentfarbstoffen
CH18161A CH422200A (de)	1960-12-06	1961-01-06	Verfahren zur Herstellung von Dithioxanthonen
BE609925A BE609925A (fr)	1960-12-06	1961-11-03	Procédé pour la fabrication de pigmentaires

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH1365960A CH386029A (de)	1960-12-06	1960-12-06	Verfahren zur Herstellung von Pigmentfarbstoffen

Publications (1)

Publication Number	Publication Date
CH386029A true CH386029A (de)	1964-12-31

Family

ID=4394237

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1365960A CH386029A (de)	1960-12-06	1960-12-06	Verfahren zur Herstellung von Pigmentfarbstoffen

Country Status (2)

Country	Link
BE (1)	BE609925A (fr)
CH (1)	CH386029A (fr)

1960
- 1960-12-06 CH CH1365960A patent/CH386029A/de unknown
1961
- 1961-11-03 BE BE609925A patent/BE609925A/fr unknown

Also Published As

Publication number	Publication date
BE609925A (fr)	1962-03-01

Publication	Publication Date	Title
DE1768892B2 (de)	1975-02-06	Disazopigmente und deren Verwendung
DE2254625C3 (de)	1979-07-19	Disazopigmente und deren Verwendung
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
DE2244035C3 (de)	1979-10-04	Disazopigmente, Verfahren zu deren Herstellung und ihre Verwendung zum Pigmentieren von hochmolekularem organischen Material
CH422200A (de)	1966-10-15	Verfahren zur Herstellung von Dithioxanthonen
CH386029A (de)	1964-12-31	Verfahren zur Herstellung von Pigmentfarbstoffen
DE2410240A1 (de)	1974-09-12	Disazopigmente, verfahren zu deren herstellung und verwendung
CH469789A (de)	1969-03-15	Verfahren zur Herstellung von Naphth-(2,3-b-)indolizin-6,11-dion-12-carbonsäure-phenylamid-Pigmenten
DE1058178B (de)	1959-05-27	Verfahren zur Herstellung von Phthalocyaninpigmenten
DE1278628B (de)	1968-09-26	Verfahren zur Herstellung von Carbonsaeureamidazofarbstoffen
DE1085630B (de)	1960-07-21	Verfahren zur Herstellung von Anthrachinonkuepenfarbstoffen
DE2350797C2 (de)	1982-10-28	Schwer lösliche Disazoverbindungen, ihre Herstellung und Verwendung als Pigmentfarbstoffe
DE2145422B2 (de)	1978-11-30	Neue Disazopigmente
DE1544556A1 (de)	1970-04-09	Azofarbstoffe und Verfahren zu deren Herstellung
DE1444772C (de)		Farbstoffe der Dioxazinreihe und Verfahren zu deren Herstellung
DE1088636B (de)	1960-09-08	Verfahren zur Herstellung von Pigmentfarbstoffen der Dioxazinreihe
CH434515A (de)	1967-04-30	Verfahren zur Herstellung neuer Monoazopigmente
CH405560A (de)	1966-01-15	Verfahren zur Herstellung reiner Kristallformen von substituierten Chinacridin-7,14-dionen
DE1274261B (de)	1968-08-01	Verfahren zur Herstellung von Monoazopigmenten
CH416668A (de)	1966-07-15	Verfahren zur Herstellung von Derivaten der Pyromellitsäure
CH413181A (de)	1966-05-15	Verfahren zur Herstellung von symmetrischen Chinacridin-7,14-dionen
DE2340956A1 (de)	1974-02-28	Schwer loesliche anthrachinonverbindungen, ihre herstellung und verwendung als pigmente
DE1544565A1 (de)	1970-04-09	Azofarbstoffe und Verfahren zu deren Herstellung
CH408944A (de)	1966-03-15	Verfahren zur Herstellung von Chinacridin-7,14-dionen