CH386029A - Process for the production of pigment dyes - Google Patents
Process for the production of pigment dyesInfo
- Publication number
- CH386029A CH386029A CH1365960A CH1365960A CH386029A CH 386029 A CH386029 A CH 386029A CH 1365960 A CH1365960 A CH 1365960A CH 1365960 A CH1365960 A CH 1365960A CH 386029 A CH386029 A CH 386029A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- cyclization
- carried out
- formula
- compounds
- Prior art date
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)
Description
Verfahren zur Herstellung von Pigmentfarbstoffen
Die Erfindung betrifft ein Verfahren zur Herstellung von Pigmentfarbstoffen der Formel
EMI1.1
In dieser Formel bedeuten A und B die zur Ergänzung zu einem aromatischen oder heterocyclischen Rest notwendigen Atome. Diese Reste sind vorzugsweise Phenylenreste oder Reste von kondensierten Ringsystemen aus 6-Ringen oder aus 6- und 5-Ringen, die durch nicht ionogene Substituenten substituiert sein können. Geeignete Reste dieser Art sind z. B. die des Naphthalins, Anthrachinons, Pyrens oder Carbazols. Nicht ionogene Substituenten der A und B enthaltenden Ringe können z. B.
Halogenatome oder Nito-, Cyan-, Trifluoralkyl-, Alkyl-, Alkoxy-, Aryl-, Aryloxy-, Azoaryl-, Arylamino-, Alkylsulfonyl-, Arylsulfonyl-, Acyl-, Acyiamino-, Amino-, Alkylamino-, Carbonsäureester- oder Sulfonsäureestergruppen sein.
Die zum Teil neuen Verbindungen (I) werden erfindungsgemäss durch intramolekulare Kondensation von Derivaten von Terephthalsäuren oder deren Estern der Formel
EMI1.2
hergestellt. In dieser Formel bedeutet R Wasserstoff oder einen Kohlenwasserstoffrest und besonders einen Alkylrest mit 1-4 Kohlenstoffatomen.
Als Kondensationsmittel wird zweckmässig eine saure Verbindung verwendet. Hierfür kommen z. B. in Betracht: Säuren der allgemeinen Formel ZSO3H, in der Z z. B. OH, C1, Alkyl, Phenyl oder Naphthyl bedeutet, insbesondere Schwefelsäure, Chlorsulfonsäure oder Methansulfonsäure, ferner Phosphor-triund -pentachlorid, Phosphorpentoxyd, Polyphosphorsäure, Phosphoroxychlorid, Thionylchlorid, Aluminiumchlorid, sowie Hydrogensulfate.
Häufig ist es günstig, die Kondensationsreaktion in Gegenwart eines Lösungsmittels durchzuführen, doch ist dies nicht erforderlich. So kann mit Aluminiumchlorid in Gegenwart eines organischen Lösungsmittels, wie z. B. Mono-, Die oder Trichlorbenzol, oder in Abwesenheit eines solchen Lösungsmittels in der Schmelze, zweckmässig dann unter Zusatz eines Flussmittels, z. B. von Natriumchlorid, kondensiert werden.
Die Wahl des Kondensationsmittels, des Lösungsmittels und der Reaktionstemperatur sowie die Mengenverhältnisse richten sich nach der Ausgangsverbindung. Verwendet man eine Ausgangsverbindung, in der die A und B enthaltenden Kerne ringaktivierende Substituenten tragen, z. B. Alkoxygruppen, und Schwefelsäure als saures Kondensationsmittel, so kondensiert man vorzugsweise in Gegenwart eines polaren organischen Lösungsmittels, wie z. B.
Äthylenglykol oder Chloressigsläure, im Temperaturbereich von etwa 100 bis 200 C. Vorzugsweise jedoch verwendet man Polyphosphorsäure von mehr als 750/o P2O5-Gehalt als Kondensationsmittel im Temperaturbereich zwischen etwa 80 und 2500 C. Dabei wird das Konden, sationsprodukt nach Verdünnen mit Wasser oft in nahezu quantitativer Ausbeute rein erhalten.
Die erhaltenen gelben, orangen oder roten Pigmente können jedoch auch leicht gereinigt werden, z. B. durch Umfällen aus Schwefelsäure, durch Umlösen, z. B. aus einem Gemisch aus Dimethylsulfoxyd und alkoholischer Kalilauge, oder durch Behandeln mit einem polaren Lösungsmittel, wie z. B.
Schwefelsäure, Dimethylformamid, Dimethylacetamid, Dimethylsulfoxyd, Piperidin, Pyridin, Äthylenglykol oder auch Chlornaphthalin, oder durch Umkristallisieren aus einem solchen Lösungsmittel.
Die erfindungsgemäss erhaltenen Verbindungen können zum Färben von Kunststoffen, insbesondere Polyvinylchlorid, wässerigen Kunstharzdispersionen zu Anstrichzwecken, Drucktinten, Lacken, Spinnmassen aus Cellulosexanthogenat (Viscosekunstseide) und Acetylcellulose (Zweieinhalb- und Triacetatkunstseide), Kautschuk, sowie von wertvollen Papieren und für den Pigmentdruck auf Textilien dienen. Manche eignen sich auch zum Färben von Polypropylen, Polyamiden (z. B. Perlon , eingetragene Schutzmarke) und Polyestern (z. B. Terylene , eingetragene Schutzmarke).
Die Färbungen von Lacken, Kunstharzdispersiot nen, Polyvinylchlorid, die Spinnfärbungen von Viscose, Acetatkunstseide und die Drucke auf Textilien sind, nebst guten Allgemeinechtheiten, durch ihre reine Nuance und eine sehr gute Lichtechtheit gekennzeichnet. Besonders hervorzuheben sind noch die hervorragende Überlackierbarkeit der Kunstharzdispersions- und der Lackfärbungen, die absolute Migrationsechtheit der Polyvinylchloridfärbungen, sowie die gute bis sehr gute Wasser-, Wasch-, Schweiss-, Überfärbe-, Alkali-, Säure-, Peroxydbleich- und Trockenreinigungsechtheit der Viscose- und Acetatkunstseide-Färbungen und der Drucke auf Textilien.
Die in den Beispielen genannten Teile sind Gewichtsteile und die Prozente Gewichtsprozente. Die Temperaturen. sind in Celsiusgraden angegeben.
Beispiel l
2,7 Teile 2 ,5-Diphenoxy-terephthalsäure werden mit 41 Teilen Polyphosphorsäure 2 Stunden auf 170 bis 1800 erwärmt. Das erhaltene Produkt wird durch Verdünnen mit Wasser abgeschieden und isoliert.
Der gelbe Rückstand wird mit 2 n-Natriumcarbonatlösung 30 Minuten bei 90-95" gerührt, dann heiss filtriert, nacheinander mit Wasser, Alkohol und Petroläther gewaschen und schliesslich getrocknet.
Die Ausbeute ist praktisch quantitativ.
Die verwendete 2,5-Diphenoxy-terephthalsäure wurde nach den Angaben von Eckert und Seidel (J. pr. Chem. 102, 359 [1921]) hergestellt.
Beispiel 2
3,0 Teile 2,5-Di-(3'-chlor-phenoxy)-terephthal- säure werden mit 60 Teilen konzentrierter Schwefelsäure 2 Stunden auf 70-80O erwärmt. Nach Abkühlen auf Raumtemperatur wird die Lösung auf 500 Teile Eiswasser gegossen. Der erhaltene gelbe Niederschlag von Dichlorxanthon wird nach den Angaben des Beispiels 1 aufgearbeitet.
An Stelle von Schwefelsäure können auch Athan- oder Methansulfonsäure oder m- und p-Toluolsulfon- säure verwendet werden. In diesem Fall erhitzt man zweckmässig 2 Stunden auf 150-180 .
Process for the production of pigment dyes
The invention relates to a process for the preparation of pigment dyes of the formula
EMI1.1
In this formula, A and B denote the atoms necessary to make up an aromatic or heterocyclic radical. These radicals are preferably phenylene radicals or radicals of fused ring systems composed of 6 rings or of 6 and 5 rings, which can be substituted by non-ionic substituents. Suitable residues of this type are, for. B. those of naphthalene, anthraquinone, pyrene or carbazole. Non-ionic substituents of the rings containing A and B can, for. B.
Halogen atoms or nito, cyano, trifluoroalkyl, alkyl, alkoxy, aryl, aryloxy, azoaryl, arylamino, alkylsulfonyl, arylsulfonyl, acyl, acyiamino, amino, alkylamino, carboxylic acid ester or Be sulfonic acid ester groups.
The compounds (I), some of which are new, are produced according to the invention by intramolecular condensation of derivatives of terephthalic acids or their esters of the formula
EMI1.2
manufactured. In this formula, R denotes hydrogen or a hydrocarbon radical and especially an alkyl radical having 1-4 carbon atoms.
An acidic compound is expediently used as the condensing agent. For this come z. B. possible: Acids of the general formula ZSO3H, in which Z z. B. OH, C1, alkyl, phenyl or naphthyl, in particular sulfuric acid, chlorosulfonic acid or methanesulfonic acid, also phosphorus triund pentachloride, phosphorus pentoxide, polyphosphoric acid, phosphorus oxychloride, thionyl chloride, aluminum chloride, and hydrogen sulfates.
It is often convenient to carry out the condensation reaction in the presence of a solvent, but this is not necessary. So can with aluminum chloride in the presence of an organic solvent, such as. B. mono-, die or trichlorobenzene, or in the absence of such a solvent in the melt, then expediently with the addition of a flux, eg. B. of sodium chloride, condensed.
The choice of the condensation agent, the solvent and the reaction temperature and the proportions depend on the starting compound. If a starting compound is used in which the nuclei containing A and B carry ring-activating substituents, e.g. B. alkoxy groups, and sulfuric acid as the acidic condensing agent, the condensation is preferably carried out in the presence of a polar organic solvent, such as. B.
Ethylene glycol or chloroacetic acid, in the temperature range from about 100 to 200 C. However, polyphosphoric acid with more than 750 / o P2O5 content is preferably used as a condensation agent in the temperature range between about 80 and 2500 C. The condensation product, after dilution with water, is often in almost quantitative yield obtained in pure form.
However, the yellow, orange or red pigments obtained can also be easily cleaned, e.g. B. by reprecipitation from sulfuric acid, by dissolving, e.g. B. from a mixture of dimethyl sulfoxide and alcoholic potassium hydroxide solution, or by treatment with a polar solvent, such as. B.
Sulfuric acid, dimethylformamide, dimethylacetamide, dimethylsulfoxide, piperidine, pyridine, ethylene glycol or chloronaphthalene, or by recrystallization from such a solvent.
The compounds obtained according to the invention can be used for coloring plastics, in particular polyvinyl chloride, aqueous synthetic resin dispersions for painting purposes, printing inks, varnishes, spinning masses made from cellulose xanthogenate (viscose artificial silk) and acetylcellulose (two-and-a-half and triacetate artificial silk), rubber, and valuable papers and for pigment printing on textiles . Some are also suitable for dyeing polypropylene, polyamides (e.g. Perlon, registered trademark) and polyesters (e.g. Terylene, registered trademark).
The dyeings of paints, synthetic resin dispersions, polyvinyl chloride, the spin dyeings of viscose, acetate rayon and the prints on textiles are characterized by their pure nuance and very good lightfastness, along with good all-round fastness properties. Particularly noteworthy are the excellent recoatability of the synthetic resin emulsion and the varnish dyeing, the absolute migration fastness of the polyvinyl chloride dyeing, as well as the good to very good fastness to water, washing, perspiration, over dyeing, alkali, acid, peroxide bleaching and dry cleaning fastness of the Viscose - and acetate rayon dyeings and prints on textiles.
The parts mentioned in the examples are parts by weight and the percentages are percentages by weight. The temperatures. are given in degrees Celsius.
Example l
2.7 parts of 2,5-diphenoxyterephthalic acid are heated to 170-1800 with 41 parts of polyphosphoric acid for 2 hours. The product obtained is precipitated and isolated by dilution with water.
The yellow residue is stirred with 2N sodium carbonate solution for 30 minutes at 90-95 ", then filtered while hot, washed successively with water, alcohol and petroleum ether and finally dried.
The yield is practically quantitative.
The 2,5-diphenoxyterephthalic acid used was prepared according to the information provided by Eckert and Seidel (J. pr. Chem. 102, 359 [1921]).
Example 2
3.0 parts of 2,5-di- (3'-chlorophenoxy) -terephthalic acid are heated to 70-80 ° for 2 hours with 60 parts of concentrated sulfuric acid. After cooling to room temperature, the solution is poured onto 500 parts of ice water. The yellow dichlorxanthone precipitate obtained is worked up as described in Example 1.
Instead of sulfuric acid, ethane or methanesulphonic acid or m- and p-toluenesulphonic acid can also be used. In this case it is expedient to heat to 150-180 for 2 hours.
Claims (1)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1365960A CH386029A (en) | 1960-12-06 | 1960-12-06 | Process for the production of pigment dyes |
| CH18161A CH422200A (en) | 1960-12-06 | 1961-01-06 | Process for the production of dithioxanthones |
| BE609925A BE609925A (en) | 1960-12-06 | 1961-11-03 | Process for the production of pigmentaries |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1365960A CH386029A (en) | 1960-12-06 | 1960-12-06 | Process for the production of pigment dyes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH386029A true CH386029A (en) | 1964-12-31 |
Family
ID=4394237
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1365960A CH386029A (en) | 1960-12-06 | 1960-12-06 | Process for the production of pigment dyes |
Country Status (2)
| Country | Link |
|---|---|
| BE (1) | BE609925A (en) |
| CH (1) | CH386029A (en) |
-
1960
- 1960-12-06 CH CH1365960A patent/CH386029A/en unknown
-
1961
- 1961-11-03 BE BE609925A patent/BE609925A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE609925A (en) | 1962-03-01 |
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