DE2050372A1 - Blue anthraquinone dispersion dyes - with improved light - and sublimation-fastness by chlorination or bromination - Google Patents
Blue anthraquinone dispersion dyes - with improved light - and sublimation-fastness by chlorination or brominationInfo
- Publication number
- DE2050372A1 DE2050372A1 DE19702050372 DE2050372A DE2050372A1 DE 2050372 A1 DE2050372 A1 DE 2050372A1 DE 19702050372 DE19702050372 DE 19702050372 DE 2050372 A DE2050372 A DE 2050372A DE 2050372 A1 DE2050372 A1 DE 2050372A1
- Authority
- DE
- Germany
- Prior art keywords
- bromine
- parts
- nitro
- chlorine
- dyes
- Prior art date
- Legal status (The legal status 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 status listed.)
- Pending
Links
- 239000000975 dye Substances 0.000 title claims abstract description 30
- 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 title 1
- 150000004056 anthraquinones Chemical class 0.000 title 1
- 230000031709 bromination Effects 0.000 title 1
- 238000005893 bromination reaction Methods 0.000 title 1
- 238000005660 chlorination reaction Methods 0.000 title 1
- 239000006185 dispersion Substances 0.000 title 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 27
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 26
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 26
- 239000000460 chlorine Substances 0.000 claims abstract description 17
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 17
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 9
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 230000026030 halogenation Effects 0.000 claims abstract description 7
- 238000005658 halogenation reaction Methods 0.000 claims abstract description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 7
- 239000003054 catalyst Substances 0.000 claims abstract description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract 3
- -1 hydroxy, nitro, carbon ester Chemical group 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- 239000000986 disperse dye Substances 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 2
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 1
- 229920000728 polyester Polymers 0.000 abstract description 13
- 125000003118 aryl group Chemical group 0.000 abstract description 2
- 125000001246 bromo group Chemical group Br* 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 2
- 238000000859 sublimation Methods 0.000 abstract description 2
- 230000008022 sublimation Effects 0.000 abstract description 2
- 239000001000 anthraquinone dye Substances 0.000 abstract 1
- 125000005521 carbonamide group Chemical group 0.000 abstract 1
- 150000001733 carboxylic acid esters Chemical class 0.000 abstract 1
- 238000004040 coloring Methods 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 abstract 1
- 229940124530 sulfonamide Drugs 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 30
- 229960000583 acetic acid Drugs 0.000 description 15
- 239000012362 glacial acetic acid Substances 0.000 description 15
- 239000000203 mixture Substances 0.000 description 15
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 230000007935 neutral effect Effects 0.000 description 7
- 239000005457 ice water Substances 0.000 description 5
- LHYQAEFVHIZFLR-UHFFFAOYSA-L 4-(4-diazonio-3-methoxyphenyl)-2-methoxybenzenediazonium;dichloride Chemical compound [Cl-].[Cl-].C1=C([N+]#N)C(OC)=CC(C=2C=C(OC)C([N+]#N)=CC=2)=C1 LHYQAEFVHIZFLR-UHFFFAOYSA-L 0.000 description 4
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 4
- DYALWCKAJBVSBZ-UHFFFAOYSA-N 1-anilino-4,5-dihydroxy-8-nitroanthracene-9,10-dione Chemical compound C1=2C(=O)C(C(=CC=C3O)[N+]([O-])=O)=C3C(=O)C=2C(O)=CC=C1NC1=CC=CC=C1 DYALWCKAJBVSBZ-UHFFFAOYSA-N 0.000 description 3
- PHLHEYMNKXWDMC-UHFFFAOYSA-N 1-anilino-4,8-dihydroxy-5-nitroanthracene-9,10-dione Chemical compound C1=2C(=O)C3=C(O)C=CC([N+]([O-])=O)=C3C(=O)C=2C(O)=CC=C1NC1=CC=CC=C1 PHLHEYMNKXWDMC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- IAEPHWWLTLOXCC-UHFFFAOYSA-N 1,5-dihydroxy-4-(2-methylanilino)-8-nitroanthracene-9,10-dione Chemical compound CC1=CC=CC=C1NC1=CC=C(O)C2=C1C(=O)C1=C(O)C=CC([N+]([O-])=O)=C1C2=O IAEPHWWLTLOXCC-UHFFFAOYSA-N 0.000 description 2
- WCRFSLKVWPIEAY-UHFFFAOYSA-N 1-(3-chloroanilino)-4,8-dihydroxy-5-nitroanthracene-9,10-dione Chemical compound C1=2C(=O)C3=C(O)C=CC([N+]([O-])=O)=C3C(=O)C=2C(O)=CC=C1NC1=CC=CC(Cl)=C1 WCRFSLKVWPIEAY-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 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
- LOBVCFOJJQRGJB-UHFFFAOYSA-N 1,8-dihydroxy-4-(2-methylanilino)-5-nitroanthracene-9,10-dione Chemical compound CC1=CC=CC=C1NC1=CC=C(O)C2=C1C(=O)C1=C([N+]([O-])=O)C=CC(O)=C1C2=O LOBVCFOJJQRGJB-UHFFFAOYSA-N 0.000 description 1
- MCKTYFMHTOKMQD-UHFFFAOYSA-N 1-(4-methylanilino)-5-nitroanthracene-9,10-dione Chemical compound C1(=CC=C(C=C1)NC1=CC=CC=2C(C3=C(C=CC=C3C(C12)=O)[N+](=O)[O-])=O)C MCKTYFMHTOKMQD-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- KYMYXNJBQUHFSN-UHFFFAOYSA-N NC(C=CC(O)=C1C(C2=C3C(O)=CC=C2NC2=CC(Cl)=CC=C2)=O)=C1C3=O Chemical compound NC(C=CC(O)=C1C(C2=C3C(O)=CC=C2NC2=CC(Cl)=CC=C2)=O)=C1C3=O KYMYXNJBQUHFSN-UHFFFAOYSA-N 0.000 description 1
- CDXZDHVYQWWDMO-UHFFFAOYSA-N NC(C=CC=C1C(C2=C3C=CC=C2NC2=CC(Cl)=CC=C2)=O)=C1C3=O Chemical compound NC(C=CC=C1C(C2=C3C=CC=C2NC2=CC(Cl)=CC=C2)=O)=C1C3=O CDXZDHVYQWWDMO-UHFFFAOYSA-N 0.000 description 1
- GZZMEFFUSRGCNW-UHFFFAOYSA-N [Br].[Br] Chemical compound [Br].[Br] GZZMEFFUSRGCNW-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 125000001424 substituent group Chemical group 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
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
- C09B1/51—N-substituted amino-hydroxy anthraquinone
- C09B1/514—N-aryl derivatives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
Description
Verfahren zur Herstellung blauer anthrachinoider Dispersionsfarbstoffe Die vorliegende Erfindung betrifft ein Verfahren zur Herstellung von blauen anthrachinoiden Dispersionsfarbstoffen mit verbesserter Lichtechtheit.Process for the production of blue anthraquinoid disperse dyes The present invention relates to a process for the preparation of blue anthraquinoids Disperse dyes with improved lightfastness.
Es ist bekannt, daß sich Farbstoffe der allgemeinen Formel I und Gemische davon, in der das eine X eine Hydroy- und das andere X eine Nitro- oder Aminogruppe bedeutet und der Ring A gegebenenfalls durch einen Rest weiter substituiert sein kann, sich zum Färben von Materialien aus aromatischen Polyestern in blauen Tönen eignen. Der Ring A kann durch Alkyl- und/oder Alkoxygruppen mit 1 bis 4 C-Atomen, Halogen, vorzugsweise Chlor- oder Brom-, Hydroxylgruppen, Nitrogruppen und/oder durch die Gruppen -CO2 R1, -CONR2R5 und -S02NR1R substituiert sein.It is known that dyes of the general formula I and mixtures thereof, in which one X denotes a Hydroxy group and the other X denotes a nitro or amino group and the ring A can optionally be further substituted by a radical, are suitable for dyeing materials made of aromatic polyesters in shades of blue. The ring A can be substituted by alkyl and / or alkoxy groups with 1 to 4 carbon atoms, halogen, preferably chlorine or bromine, hydroxyl groups, nitro groups and / or by the groups -CO2 R1, -CONR2R5 and -S02NR1R.
In den Alkyl- und Alkoxygruppen können gegebenenfalls ein oder mehrere Wasserstoffatome durch Substituenten wie Hydroxyl-, Alkoxy-, Cyan-, Amino- und Carbonestergruppen ersetzt sein.In the alkyl and alkoxy groups, one or more can optionally Hydrogen atoms through substituents such as hydroxyl, alkoxy, cyano, amino and carbon ester groups be replaced.
Tn den Formeln bedeuten R Wasserstff, eine Alkyl- oder Hydroxyalkylgruppe, R2 und R3, die gleich oder verschieden sein können, Wasserstoff oder gegebenenfalls durch Hydroxyl-, Alkoxy-, Amino-oder Cyangruppen substituierte Alkylgruppen mit 1 bis 6 Kohlenstoffatomen und/oder aliphatische Ringe mit 3 bis 7 Kohlenstoffatomen. Die Reste R2 und R3 können außerdem zusammen mit dem Amidstickstofif' einen gesättigten heterocyclischen 5- oder 6-Ring 418-70 Als typische Vertreter der Farbstoffe der Formel I seien beispielsweise genannt: 1.5-Dihydroxy-4-anilino-8-nitro-anthrachinon 1.5- " -4- " -8-amino- " 1.5- " -4(2'-toluidino)-8-nitro- " 1.5- " -4(3'- " )-8- " " 1.5 " -4(4'- " )-8- " " 1.5 " -4(4'- " )-8-amino- " 1.5- " -4(2',4'-dimethylanilino)-8-nitro-anthrachinon 1.5- " -4(2'-chloranilino)-8- " " 1.5- " -4(3'- " )-8- " " 1.5- " -4(4'- " )-8- " " 1.5- " -4(3'- " )-8-amino-anthrachinon 1.8- " -4-aniline-5-nitro-anthrachinon 1.8- " -4- " -5-amino-1.8- " -4(2'-toluidino)-5-nitro-anthrachinon 1.8- " -4(3'- " )-5- " " 1.8- " -4(4'- " )-5- " " 1.8- " -4(4'- " )-5-amino- " 1.8- " -4(2',4'-dimethylanilino)-5-nitro-anthrachinon 1.8- " -4(2'-chloranilino)-5- " " 1.8- " -4(3'- " )-5- " " 1.8- " -4(4'- )-5- " " 1.8- " -4(3'- " )-5-amino-anthrachinon.In the formulas, R denotes hydrogen, an alkyl or hydroxyalkyl group, R2 and R3, which can be identical or different, hydrogen or optionally alkyl groups substituted by hydroxyl, alkoxy, amino or cyano groups 1 to 6 carbon atoms and / or aliphatic rings with 3 to 7 carbon atoms. The residues R2 and R3 can also be saturated together with the amide nitrogen heterocyclic 5- or 6-membered ring 418-70 As a typical representative of the Examples of dyes of the formula I are: 1,5-dihydroxy-4-anilino-8-nitro-anthraquinone 1.5- "-4-" -8-amino- "1.5-" -4 (2'-toluidino) -8-nitro- "1.5-" -4 (3'- ") -8- "" 1.5 "-4 (4'-") -8- "" 1.5 "-4 (4'-") -8-amino- "1.5-" -4 (2 ', 4'-dimethylanilino) -8- nitro-anthraquinone 1.5- "-4 (2'-chloroanilino) -8-" "1.5-" -4 (3'- ") -8-" "1.5-" -4 (4'- ") -8- "" 1.5- "-4 (3'-") -8-amino-anthraquinone 1.8- "-4-aniline-5-nitro-anthraquinone 1.8- "-4-" -5-amino-1.8- "-4 (2'-toluidino) -5-nitro-anthraquinone 1.8-" -4 (3'- ") -5-" "1.8-" -4 (4'- ") -5-" "1.8-" -4 (4'- ") -5-amino-" 1.8- "-4 (2 ', 4 '-dimethylanilino) -5-nitro-anthraquinone 1.8- "-4 (2'-chloroanilino) -5-" "1.8-" -4 (3'- ") -5-" "1.8-" -4 (4'-) -5- " "1.8-" -4 (3'- ") -5-amino-anthraquinone.
Es wurde nun gefunden, daß man überraschenderweise Farbstoffe mit wesentlich verbesserter Lichtechtheit erhält, wenn man die Farbstoffe der Formel I mit Chlor oder Brom oder mit chlor-oder bromabgebenden Mitteln oder Gemischen davon gegebenenfalls in Gegenwart von Halogenierungskatalysatoren behandelt.It has now been found that, surprisingly, dyes with Significantly improved lightfastness is obtained when using the dyes of the formula I with chlorine or bromine or with chlorine- or bromine-releasing agents or mixtures thereof optionally treated in the presence of halogenation catalysts.
So steigt zum Beispiel beim Nachbehandeln des Farbstoffs der Formel
II mit Brom in Eisessig, wobei im Mittel zwei Bromatome in das Molekül des Farbstoffs
II eintreten, die Lichtechtheit um eine Stufe des Blaumaßstabes an. In gleicher
Weise steigt dabei auch gleichzeitig die Sublimierechtheit der mit dem Reaktionsprodukt
III erhaltenen Färbung.
Die folgenden Beispiele erläutern das Verfahren der Erfindung.The following examples illustrate the process of the invention.
Die genannten Teile und Prozentangaben beziehen sich auf das Gewicht. Die Volumenteile verhalten sich zu den Gewichtsteilen wie das Liter zum Kilogramm.The parts and percentages mentioned relate to weight. The parts by volume are related to the parts by weight as the liter is to the kilogram.
Beispiel 1 10,3 Teile l,5-Dihydroxy-4(m-chloranilino)-8-nitro-anthrachinon werden in 120 Volumenteilen Eisessig suspendiert. Bei 500C werden 8,8 Teile Brom in 20 Volumenteilen Eisessig zugetropft. Example 1 10.3 parts of 1,5-dihydroxy-4 (m-chloroanilino) -8-nitro-anthraquinone are suspended in 120 parts by volume of glacial acetic acid. At 50 ° C. there are 8.8 parts of bromine added dropwise in 20 parts by volume of glacial acetic acid.
Man häl die lseaktionsmischung 5 Stunden bei 75 0C, gießt diese dann in Eiswasser und saugt den Farbstoff ab und wäscht neutral.The reaction mixture is kept at 75 ° C. for 5 hours and is poured then in ice water and sucks off the dye and washes neutral.
Der isolierte Farbstoff enthält 28,2 % Brom. Er färbt Polyester in hochechten blauen Tönen an.The isolated dye contains 28.2% bromine. He dyes polyester in high-quality blue tones.
Beispiel 2 9,4 Teile eines Gemisches aus etwa gleichen Teilen 1.5-Dihydroxy-4-anilino-8-nitro-anthrachinon und 1 .8-Dihydroxy-4-anilino-5-nitro-anthrachinon werden in 120 Volumenteilen Eisessig suspendiert. Bei 50 0C tropft man 16 Teile Brom in 25 Volumenteilen Eisessig zu. Die Mischung wird 7 Stunden auf 800C erwärmt. Dann gießt man in Eiswasser, saugt ab und wäscht mit Wasser neutral. Example 2 9.4 parts of a mixture of approximately equal parts of 1,5-dihydroxy-4-anilino-8-nitro-anthraquinone and 1,8-dihydroxy-4-anilino-5-nitro-anthraquinone are in 120 parts by volume of glacial acetic acid suspended. At 50 ° C., 16 parts of bromine in 25 parts by volume of glacial acetic acid are added dropwise. The mixture is heated to 80 ° C. for 7 hours. Then you pour into ice water, suck and washes neutral with water.
Der isolierte Farbstoff enthält 57,0 % Brom. Er färbt Polyester in hochechten blauen Tönen an.The isolated dye contains 57.0% bromine. He dyes polyester in high-quality blue tones.
Beispiel 5 22,6 Teile eines Gemisches aus etwa gleichen Teilen 1.5-Dihydroxy-4-anilino-8-nitro-anthrachinon und 1.8-Dihydroxy-4-anilino-5-nitro-anthrachinon werden in 170 Teilen Nitrobenzol mit 41 Teilen Sulfurylchlorid 5 Stunden auf 650C erwärmt. Danach treibt man das Nitrobenzol mit Wasserdampf ab, saugt ab und wäscht mit Wasser. Der isolierte Farbstoff enthält 28,8 ffi Chlor. Example 5 22.6 parts of a mixture of approximately equal parts of 1,5-dihydroxy-4-anilino-8-nitro-anthraquinone and 1,8-dihydroxy-4-anilino-5-nitro-anthraquinone are in 170 parts of nitrobenzene heated with 41 parts of sulfuryl chloride at 65 ° C. for 5 hours. Then you do it Nitrobenzene with steam, sucks off and washed with water. The isolated dye contains 28.8 ffi chlorine.
Er färbt Polyester in hochechten blauen Tönen an.It stains polyester in extremely fast blue tones.
Beispiel 4 10,5 Teile des in Beispiel 3 isolierten Farbstoffs werden in 80 Teilen Wasser und 6 Teilen 30-prozentiger Natronlauge 15 Minuten gerührt. Danach gibt man eine Lösung von 15 Teilen kristallisiertem Natriumsulfid in 20 Teilen Wasser zu, erhitzt 2,5 Stunden auf 900C' verdünnt anschließend mit 100 Teilen Wasser und saugt ab. Den Rückstand kocht man mit verdünnter Salzsäure auf, saugt erneut ab und wäscht mit Wasser neutral. Example 4 10.5 parts of the dye isolated in Example 3 become stirred in 80 parts of water and 6 parts of 30 percent sodium hydroxide solution for 15 minutes. A solution of 15 parts of crystallized sodium sulfide in 20 parts is then added Water to, heated for 2.5 hours at 90 ° C., then diluted with 100 parts of water and sucks. The residue is boiled up with dilute hydrochloric acid and suctioned again and washes neutral with water.
Der isolierte Farbstoff enthält 29'ru ffi Chlor. Er farbt Polyester in hochechten blauen Tönen an.The isolated dye contains 29'ru ffi chlorine. He colors polyester in real blue tones.
Beispiel 5 9,75 Teile eines Gemisches aus etwa gleichen Teilen 1.5-Dihydroxy-4-(o-toluidino)-8-nitro-anthrachinon und 1.8-Dihydroxy-4(o-toluidino)-5-nitro-anthrachinon und 8,1 Teilen Sulfurylchlorid werden in 70 Teilen Nitrobenzol 5 Stunden auf 550C erwärmt. Danach wird das Nitrobenzol mit Wasserdampf abgetrieben, der Rückstand abgesaugt und mit Wasser gewaschen. Der isolierte Farbstoff enthält 15,2 % Chlor. Er färbt Polyester in hochechten blauen Tönen an. Example 5 9.75 parts of a mixture of approximately equal parts of 1,5-dihydroxy-4- (o-toluidino) -8-nitro-anthraquinone and 1,8-dihydroxy-4 (o-toluidino) -5-nitro-anthraquinone and 8.1 parts of sulfuryl chloride are heated in 70 parts of nitrobenzene at 550C for 5 hours. Then the nitrobenzene Stripped off with steam, suction filtered and the residue washed with water. Of the isolated dye contains 15.2% chlorine. It dyes polyester in high-speed blue Tones on.
Beispiel 6 20,5 Teile eines Gemisches aus etwa gleichen Teilen 1.5-Dihydroxy-4(m-chloranilino)-8-amino-anthrachinon und 1.8-Dihydroxy-4(m-chloranilino)-5-amino-anthrachinon werden in 240 Volumenteilen Eisessig suspendiert. Bei 500C tropft man 19,2 Teilen Brom in 25 Volumenteilen Eisessig zu und hält 8 Stunden bei 750C. Dann wird in Eiswasser gegossen, abgesaugt und neutral gewaschen. Der isolierte Farbstoff enthält )1,2 % Brom. Er färbt Polyester in hochechten blauen Tönen an. Example 6 20.5 parts of a mixture of approximately equal parts of 1,5-dihydroxy-4 (m-chloroanilino) -8-amino-anthraquinone and 1.8-dihydroxy-4 (m-chloroanilino) -5-amino-anthraquinone are in 240 parts by volume Glacial acetic acid suspended. 19.2 parts of bromine in 25 parts by volume of glacial acetic acid are added dropwise at 50.degree and holds 8 hours at 750C. Then it is poured into ice water, suctioned off and neutral washed. The isolated dye contains 1.2% bromine. He dyes polyester in high fastness blue tones.
Beispiel 7 18,8 Teile 1.8-Dihydroxy-4-anilino-5-nitro-anthrachinon werden in 240 Volumenteilen Eisessig suspendiert. Bei 50°C tropft man 52 Teile Brom in 50 Volumenteilen Eisessig zu. Die Mischung wird 7 Stunden auf 8o 0C erwärmt. Ddnn gießt man in Eiswasser, saugt ab und wäscht mit Wasser neutral. Der isolierte Farbstoff enthält 56,8 % Brom. Er färbt Polyester in hochechten blauen Tönen an Beispiel 8 9,75 Teile eines Gemisches aus etwa gleichen Teilen 1.5-Dihydroxy-4(o-toluidino)-8-nitro-anthrachinon und 1.8-Dihydroxy-4(o-toluidino)-5-nitro-anthrachinon werden in 120 Volumenteilen Eisessig suspendiert. Bei 50°C tropft man 4,4 Teile Brom in 15 Volumenteilen Eisessig zu. Die Mischung wird 8 Stunden auf 75 0C erwärmt. Dann gießt man in Eisessig, saugt ab und wäscht mit Wasser neutral. Der isolierte Farbstoff enthält 18,5 % Brom. Er färbt Polyester in hochechten blauen Tönen an. Example 7 18.8 parts of 1,8-dihydroxy-4-anilino-5-nitro-anthraquinone are suspended in 240 parts by volume of glacial acetic acid. 52 parts of bromine are added dropwise at 50.degree in 50 parts by volume of glacial acetic acid. The mixture is heated to 80 ° C. for 7 hours. It is then poured into ice water, suctioned off and washed neutral with water. The isolated one The dye contains 56.8% bromine. It stains polyester in extremely fast blue tones Example 8 9.75 parts of a mixture of approximately equal parts of 1,5-dihydroxy-4 (o-toluidino) -8-nitro-anthraquinone and 1.8-dihydroxy-4 (o-toluidino) -5-nitro-anthraquinone are in 120 parts by volume Glacial acetic acid suspended. 4.4 parts of bromine are added dropwise at 50.degree 15 parts by volume Glacial acetic acid too. The mixture is heated to 75 ° C. for 8 hours. Then you pour in glacial acetic acid, sucks off and washes neutral with water. The isolated dye contains 18.5% bromine. It stains polyester in extremely fast blue tones.
Beispiel 9 Teile eines Gemisches aus etwa gleichen Teilen 1.5-Dihydroxy-4(m-chloranilino)-8-nitro-anthrachinon und 1.8-Dihydroxy-4(m-chloranilino)-5-nitro-anthrachinon werden in 80 Volumenteilen Nitrobenzol suspendiert. Bei 170°C werden nun in 1,5 Stunden 8 Teile Chlor eingeleitet. Man läßt abkühlen und gießt in 1000 Volumenteilen Methanol, saugt ab und wäscht mit Wasser. Der isolierte Farbstoff enthält 18,2 % Chlor Er färbt Polyester in hochechten blauen Tönen an. Example 9 parts of a mixture of approximately equal parts of 1,5-dihydroxy-4 (m-chloroanilino) -8-nitro-anthraquinone and 1.8-dihydroxy-4 (m-chloroanilino) -5-nitro-anthraquinone are in 80 parts by volume Nitrobenzene suspended. 8 parts of chlorine are then passed in at 170 ° C. in the course of 1.5 hours. It is allowed to cool and poured into 1000 parts by volume of methanol, filtered off with suction and washed with water. The isolated dye contains 18.2% chlorine. It dyes polyester in high-fastness blue tones.
Beispiel 10 12,1 Teile eines Gemisches aus etwa gleichen Teilen 1.5-Dihvdroxy-4(2' ,4t -dimethylanilino)-8-nitrc-anthrachinon und 1.8-Dihydroxy-4(2',4'-dimethylanilino)-5-nitro-anthraehinon werden in 120 Volumenteilen Eisessig suspendiert. Bei Siedetemperatur tropft man nun 9,6 Teile Brom in 20 Volumenteilen Eisessig zu und hält 1,5 Stunden bei dieser Temperatur. Dann gießt man in Eiswasser, saugt ab und wäscht mit Wasser neutral. Example 10 12.1 parts of a mixture of approximately equal parts 1,5-Dihvdroxy-4 (2 ' , 4t -dimethylanilino) -8-nitrc-anthraquinone and 1,8-dihydroxy-4 (2 ', 4'-dimethylanilino) -5-nitro-anthraehinone are suspended in 120 parts by volume of glacial acetic acid. At the boiling point one drips now 9.6 parts of bromine in 20 parts by volume of glacial acetic acid are added and they are kept there for 1.5 hours Temperature. It is then poured into ice water, filtered off with suction and washed neutral with water.
Der isolierte Farbstoff enthält 25,2 ß Brom. Er färbt Polyester in hochechten blauen oen an.The isolated dye contains 25.2 μl of bromine. He dyes polyester in high-quality blue oen.
Beispiel 11 9,75 Teile eines Gemisches aus etwa gleichen Teilen 1.5-Dihydroxy-4(p-toluidino)-8-nitro-anthrachinon und 1.8-Dihydroxy-4(p-toluidino)-5-nitro-anthrachinon werden in 70 Teilen robenzol mit 8,1 Teilen Sulfurylclhlorid 5 Stunden auf 650C erwärmt. Danach treibt man das Nitrobenzol mit Wasserdampf ab, saugt ab und wäscht mit Wasser. Der isolierte Farbstoff enthält 16,4 ffi Chlor. Er färbt Polyester in hochechten blauen Tönen an.. Example 11 9.75 parts of a mixture of approximately equal parts of 1,5-dihydroxy-4 (p-toluidino) -8-nitro-anthraquinone and 1.8-dihydroxy-4 (p-toluidino) -5-nitro-anthraquinone are robenzene in 70 parts heated with 8.1 parts of sulfuryl chloride for 5 hours at 650.degree. Then you do it Nitrobenzene with steam, sucks off and washed with water. The isolated dye contains 16.4 ffi chlorine. It stains polyester in extremely fast blue tones.
Claims (4)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702050372 DE2050372A1 (en) | 1970-10-14 | 1970-10-14 | Blue anthraquinone dispersion dyes - with improved light - and sublimation-fastness by chlorination or bromination |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702050372 DE2050372A1 (en) | 1970-10-14 | 1970-10-14 | Blue anthraquinone dispersion dyes - with improved light - and sublimation-fastness by chlorination or bromination |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2050372A1 true DE2050372A1 (en) | 1972-04-20 |
Family
ID=5785067
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702050372 Pending DE2050372A1 (en) | 1970-10-14 | 1970-10-14 | Blue anthraquinone dispersion dyes - with improved light - and sublimation-fastness by chlorination or bromination |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE2050372A1 (en) |
-
1970
- 1970-10-14 DE DE19702050372 patent/DE2050372A1/en active Pending
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