CH684597A5 - Mixtures of dispersion dyes. - Google Patents
Mixtures of dispersion dyes. Download PDFInfo
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- CH684597A5 CH684597A5 CH3507/92A CH350792A CH684597A5 CH 684597 A5 CH684597 A5 CH 684597A5 CH 3507/92 A CH3507/92 A CH 3507/92A CH 350792 A CH350792 A CH 350792A CH 684597 A5 CH684597 A5 CH 684597A5
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- alkyl
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- dye
- dyes
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- 239000000975 dye Substances 0.000 title claims description 76
- 239000000203 mixture Substances 0.000 title claims description 35
- 239000006185 dispersion Substances 0.000 title 1
- 239000000460 chlorine Substances 0.000 claims description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 239000000986 disperse dye Substances 0.000 claims description 8
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- -1 phenylaminocarbonyl Chemical group 0.000 claims description 6
- 125000005359 phenoxyalkyl group Chemical group 0.000 claims description 5
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 14
- 230000008878 coupling Effects 0.000 description 9
- 238000010168 coupling process Methods 0.000 description 9
- 238000005859 coupling reaction Methods 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 238000004043 dyeing Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000000835 fiber Substances 0.000 description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- 238000000227 grinding Methods 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical class C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 229920001732 Lignosulfonate Polymers 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 2
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 2
- 235000011130 ammonium sulphate Nutrition 0.000 description 2
- 238000000889 atomisation Methods 0.000 description 2
- ZHZPDMZPDWXVMJ-UHFFFAOYSA-N benzyl 2-aminobenzoate Chemical compound NC1=CC=CC=C1C(=O)OCC1=CC=CC=C1 ZHZPDMZPDWXVMJ-UHFFFAOYSA-N 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- 150000001989 diazonium salts Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- RLXXBBHXOBWALJ-UHFFFAOYSA-N 2-phenoxyethyl 2-aminobenzoate Chemical compound NC1=CC=CC=C1C(=O)OCCOC1=CC=CC=C1 RLXXBBHXOBWALJ-UHFFFAOYSA-N 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- 229920001410 Microfiber Polymers 0.000 description 1
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 1
- VJMAITQRABEEKP-UHFFFAOYSA-N [6-(phenylmethoxymethyl)-1,4-dioxan-2-yl]methyl acetate Chemical compound O1C(COC(=O)C)COCC1COCC1=CC=CC=C1 VJMAITQRABEEKP-UHFFFAOYSA-N 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000002947 alkylene 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
- 239000007900 aqueous suspension Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229960000956 coumarin Drugs 0.000 description 1
- 235000001671 coumarin Nutrition 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000009998 heat setting Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- 239000003658 microfiber Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- RWZYAGGXGHYGMB-UHFFFAOYSA-N o-aminobenzenecarboxylic acid Natural products NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical class OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010023 transfer printing Methods 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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/0041—Blends of pigments; Mixtured crystals; Solid solutions mixtures containing one azo dye
-
- 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
- C09B57/02—Coumarine dyes
Description
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CH 684 597 A5 CH 684 597 A5
Beschreibung description
Es wurde gefunden, dass man sehr echte, brillant grünstichig-gelbe Färbungen auf Fasern und Fasermaterial aus voll- oder halbsynthetischen, hochmolekularen, hydrophoben organischen Verbindungen erhält, wenn man diese mit einem Gemisch von Dispersionsfarbstoffen, enthaltend 25 bis 85 Gewichtsprozent eines Farbstoffs der allgemeinen Formel I It has been found that very real, brilliant greenish-yellow dyeings on fibers and fiber material from fully or semisynthetic, high-molecular, hydrophobic organic compounds are obtained when these are mixed with a mixture of disperse dyes containing 25 to 85 percent by weight of a dye of the general formula I.
ch. cn ch. cn
H—= X X=^C0-0-R H— = X X = ^ C0-0-R
oh r oh r
2 2nd
worin Ri gegebenenfalls ein- oder zweimal im Phenylkern durch Chlor, Brom, Ci-2-Alkyl oder Ci-4-Alk-oxy substituiertes H5C6-(-0-GH2-CH2)n- oder Phenyl-Ci-3-alkyl, in which Ri is H5C6 - (- 0-GH2-CH2) n- or phenyl-Ci-3-alkyl optionally substituted once or twice in the phenyl nucleus by chlorine, bromine, Ci-2-alkyl or Ci-4-alk-oxy,
R2 C-i-6-Alkyl, Ci-6-Alkoxy-C2-3-alkyl, Hydroxy-C2-3-alkoxy-C2-3-alkyl oder Ci-4-Alkoxy-C2-3-alkoxy-C2-3-alkyl und n 1, 2 oder 3 bedeuten, R2 Ci-6-alkyl, Ci-6-alkoxy-C2-3-alkyl, hydroxy-C2-3-alkoxy-C2-3-alkyl or Ci-4-alkoxy-C2-3-alkoxy-C2-3-alkyl and n is 1, 2 or 3,
5 bis 50 Gewichtsprozent eines Farbstoffs der Formel II 5 to 50 percent by weight of a dye of the formula II
' JÇO"" 'JÇO ""
H \ H \
R3 und R4 Ci-4-Alkyl, vorzugsweise Äthyl und R3 and R4 Ci-4-alkyl, preferably ethyl and
R5 Ci-4-Alkyl oder ein Halogenatom, vorzugsweise ein Chloratom bedeuten und 0 bis 35 Gewichtsprozent eines Farbstoffs der Formel III oder IV R5 is Ci-4-alkyl or a halogen atom, preferably a chlorine atom and 0 to 35 percent by weight of a dye of the formula III or IV
fK"0 fK "0
(i), (i),
(in), (in),
(iv), (iv),
worin R6 Ci-6-Alkyl oder Phenyl-Ci-2-alkyl, wherein R6 is Ci-6-alkyl or phenyl-Ci-2-alkyl,
R7 gegebenenfalls im Kern durch 1 oder zwei Halogenatome, vorzugsweise Chlor, substituiertes Phenylaminocarbonyl, durch Ci-4-Alkoxycarbonyl substituiertes Benzoyl, para-Cyclohexylphenyl oder, nur in Formel III, eine Gruppe der Formel R7 optionally substituted by 1 or two halogen atoms, preferably chlorine, phenylaminocarbonyl, benzoyl substituted by Ci-4-alkoxycarbonyl, para-cyclohexylphenyl or, only in formula III, a group of the formula
2 2nd
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CH 684 597 A5 CH 684 597 A5
/CN / CN
-C0-C2-4-Alkylen-C0-0-C2-3-Alkylen-N(Ci-6-AIkyl) y-ch=c bedeuten, oder einem -C0-C2-4-alkylene-C0-0-C2-3-alkylene-N (Ci-6-alkyl) y-ch = c, or one
Xaf Xaf
Gemisch von zwei oder mehreren Farbstoffen der Formel I (worin die Gruppe der Formel -CO-O-Ri vorzugsweise in ortho-Stellung zur Azogruppe gebunden ist) wobei in diesem Gemisch von Farbstoffen, wenn Ri nur gegebenenfalls substituiertes Benzyl ist, mindestens 10 Gewichtsprozente eines oder mehrerer Farbstoffe, worin R2 Ci-6-Alkoxy-C2-3-alkyl bedeutet, enthalten sind, während im Gemisch mit mindestens 10 Gewichtsprozenten eines Farbstoffs, worin Ri gegebenenfalls substituiertes Phenoxyalkyl ist, beliebige andere Farbstoffe der Formel I mit der Gruppe der Formel -CO-O-Ri in ortho-Stellung zur Azogruppe anwesend sein können, färbt, klotzfärbt oder bedruckt. Diese Dispersionsfarbstoff-Gemische sind Gegenstand der vorliegenden Erfindung. Mixture of two or more dyes of the formula I (in which the group of the formula -CO-O-Ri is preferably bonded in the ortho position to the azo group), in which mixture of dyes, if Ri is only optionally substituted benzyl, at least 10 percent by weight or more dyes, in which R2 is Ci-6-alkoxy-C2-3-alkyl, are contained, while in admixture with at least 10 percent by weight of a dye, in which Ri is optionally substituted phenoxyalkyl, any other dyes of the formula I with the group of the formula -CO-O-Ri may be present in the ortho position to the azo group, colors, block colors or prints. These disperse dye mixtures are the subject of the present invention.
Bevorzugt sind die Gemische von Dispersionsfarbstoffen, die 45 bis 75 Gewichtsprozent eines Farbstoffs der Formel I, 15 bis 30 Gewichtsprozent eines Farbstoffs der Formel II und 0 bis 30, insbesondere 15 bis 25 Gewichtsprozent eines Farbstoffs der Formel III enthalten. Preference is given to the mixtures of disperse dyes which contain 45 to 75 percent by weight of a dye of the formula I, 15 to 30 percent by weight of a dye of the formula II and 0 to 30, in particular 15 to 25 percent by weight of a dye of the formula III.
Gleichermassen bevorzugt sind auch die Dispersionsfarbstoff-Gemische, der Formel la c0-0-r^ ch3 The disperse dye mixtures of the formula la c0-0-r ^ ch3 are equally preferred
(Ia), (Ia),
worin Ri eine Benzyl- oder Phenoxy-äthylgruppe, where Ri is a benzyl or phenoxyethyl group,
R2 C3_4-Alkyl oder Ci-6-Alkoxy-C2-3-alkyl, vorzugsweise n-Butyl oder C2-4-Alkoxy-C2-3-alkyl bedeuten, R2 is C3_4-alkyl or Ci-6-alkoxy-C2-3-alkyl, preferably n-butyl or C2-4-alkoxy-C2-3-alkyl,
wobei in diesem Gemisch von Farbstoffen, wenn Ri Benzyl ist, mindestens 10 Gewichtsprozente eines oder mehrerer Farbstoffe, worin R2 Ci-6-Alkoxy-C2-3-alkyl bedeutet, enthalten sind, während im Gemisch mit mindestens 10 Gewichtsprozenten eines Farbstoffs, worin Ri Phenoxyalkyl ist, beliebige andere Farbstoffe der Formel la anwesend sein können. wherein in this mixture of dyes, when Ri is benzyl, at least 10 percent by weight of one or more dyes, in which R2 is Ci-6-alkoxy-C2-3-alkyl, are contained, while in a mixture with at least 10 percent by weight of a dye, in which Ri Phenoxyalkyl is, any other dyes of the formula la can be present.
Falls nichts anderes angegeben ist, sind die genannten Alkyl-, Alkylen- und Alkenylreste geradkettig. Die Einzelfarbstoffe der Formeln I bis IV sind grösstenteils bekannt; soweit sie nicht bekannt sind, lassen sie sich leicht in Analogie zur Synthese ähnlicher Farbstoffe, herstellen. Unless stated otherwise, the alkyl, alkylene and alkenyl radicals mentioned are straight-chain. The majority of the individual dyes of the formulas I to IV are known; if they are not known, they can easily be prepared in analogy to the synthesis of similar dyes.
Die Herstellung der neuen Farbstoffgemische erfolgt durch einfaches Vermischen der Einzelkomponenten, was vor dem Dispergieren (Feinmahlung) der Farbstoffe oder danach geschehen kann. Vorzugsweise wird den Farbstoffpräparaten ein übliches Dispergiermittel beigemischt. The new dye mixtures are prepared by simply mixing the individual components, which can be done before or after the dispersing (fine grinding) of the dyes. A customary dispersant is preferably added to the dye preparations.
Die Farbstoffgemische der Formel I werden vorzugsweise durch Kuppeln eines diazotierten Amins oder eines Gemisches von diazotierten Aminen der Formel V The dye mixtures of the formula I are preferably obtained by coupling a diazotized amine or a mixture of diazotized amines of the formula V.
c0-0-r, c0-0-r,
-IF%—NH- -IF% —NH-
II -\Jj—^2 II - \ Jj— ^ 2
mit einer Verbindung oder einem Gemisch von Verbindungen der Formel VI with a compound or a mixture of compounds of the formula VI
cn cn
(vi) (vi)
hergestellt, wobei für den Fall, dass im Amin der Formel V Ri einheitlich Benzyl ist, ein Gemisch von Verbindungen der Formel VI verwendet wird, in dem mindestens 10 Gewichtsprozente Alkoxyalkyl-sub-stituiert sind, und für den Fall, dass mindestens 10 Gewichtsprozente eines Amins der Formel II eingesetzt werden, worin Ri Phenoxyalkyl bedeutet, beliebige andere Farbstoffkomponenten vorhanden sein können. prepared, in the event that benzyl is uniform in the amine of the formula V Ri, a mixture of compounds of the formula VI is used in which at least 10 percent by weight alkoxyalkyl is substituted, and in the event that at least 10 percent by weight one Amines of the formula II are used, in which R 1 is phenoxyalkyl, any other dye components can be present.
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CH 684 597 A5 CH 684 597 A5
Die (im Benzolkern Substituenten tragenden) Anthranilsäurebenzyl- bzw. -phenoxyalkylester der Formel V sind grösstenteils bekannt; soweit sie noch nicht beschrieben sind, können sie auf eine dem Fachmann bekannte Weise leicht hergestellt werden. Die Pyridonverbindungen der Formel VI sind bekannt. Diazotieren und Kuppeln erfolgen auf übliche Weise. The benzyl or phenoxyalkyl anthranilic acid (bearing substituents in the benzene nucleus) of the formula V are largely known; if they have not yet been described, they can easily be produced in a manner known to the person skilled in the art. The pyridone compounds of formula VI are known. Diazotization and coupling are carried out in the usual way.
Die Verarbeitung der neuen Dispersionsfarbstoffmischungen zu Färbepräparaten erfolgt auf allgemein bekannte Weise, z.B. durch Mahlen in Gegenwart von Dispergier- und/oder Füllmitteln. Mit den gegebenenfalls im Vakuum oder durch Zerstäuben getrockneten Präparaten kann man, nach Zugabe von mehr oder weniger Wasser, in sogenannter kurzer oder langer Flotte färben, klotzen oder bedrucken. The processing of the new disperse dye mixtures into dyeing preparations is carried out in a generally known manner, e.g. by grinding in the presence of dispersants and / or fillers. With the preparations which may have been dried in vacuo or by atomization, after adding more or less water, it is possible to dye, pad or print in a so-called short or long liquor.
Die Farbstoffmischungen ziehen aus wässriger Suspension ausgezeichnet auf Textilmaterial aus vollsynthetischen oder halbsynthetischen, hydrophoben hochmolekularen organischen Stoffen auf. Besonders geeignet sind sie zum Färben oder Bedrucken von Textilmaterial aus linearen, aromatischen Po-lyestern, sowie aus Cellulose-21/2-acetat und Cellulosetriacetat. Sie eignen sich ausgezeichnet für das Färben von sogenannten Microfasern und sind auch für das Thermo-Transfer-Printing geeignet. The dyestuff mixes excellently from an aqueous suspension onto textile material made from fully synthetic or semi-synthetic, hydrophobic, high molecular weight organic substances. They are particularly suitable for dyeing or printing textile material made from linear, aromatic polyesters, as well as from cellulose 21/2 acetate and cellulose triacetate. They are ideal for dyeing so-called microfibers and are also suitable for thermal transfer printing.
Man färbt oder bedruckt nach an sich bekannten, z.B. den in der französischen Patentschrift Nr. 1 445 371 beschriebenen Verfahren. One dyes or prints according to known, e.g. the methods described in French Patent No. 1,445,371.
Die erhaltenen Färbungen besitzen gute bis sehr gute Allgemeinechtheiten; hervorzuheben sind die Lichtechtheit, die Thermofixier-, Sublimier- und Plissierechtheit. Ein weiterer Vorzug der erfindungsge-mässen Farbstoffe liegt im hohen Aufbauvermögen, der hohen Auszieh- bzw. Fixiergeschwindigkeit und dem guten Badauszug begründet. The dyeings obtained have good to very good general fastness properties; The fastness to light, the heat-setting, sublimation and pleating fastness are to be emphasized. Another advantage of the dyes according to the invention lies in the high build-up capacity, the high pull-out or fixing speed and the good bath extract.
Es ist überraschend, dass die Fluoreszenz der im Gemisch vorhandenen Cumarinfarbstoffe (der Formel II) selbst in der Kombination mit Blaufarbstoffen aller Klassen (z.B. Azo, Anthrachinon und Methin) nicht gelöscht wird, das heisst, die so erhaltenen Grünkombinationen zeigen eine hervorragende Brillanz. It is surprising that the fluorescence of the coumarin dyes present in the mixture (of the formula II) is not quenched even in the combination with blue dyes of all classes (e.g. azo, anthraquinone and methine), i.e. the green combinations obtained in this way show an excellent brilliance.
Gemäss den folgenden Beispielen werden die Farbstoffe der Tabellen 1 bis 3 verwendet. Die Farbstoffe der Tabelle 1 entsprechen der Formel I' According to the following examples, the dyes in Tables 1 to 3 are used. The dyes in Table 1 correspond to the formula I '
Tabelle 1 Table 1
Farbstoff No. Dye No.
ri ri
Substitutions-position r2- Substitution position r2-
1 1
H5C6-O-CH2CH2- H5C6-O-CH2CH2-
2- 2-
-C4H9/-C3H6-O-C4H9 (1:1) -C4H9 / -C3H6-O-C4H9 (1: 1)
2 2nd
H5C6—CH2— H5C6 — CH2—
2- 2-
-(CH2)3-OC2H5 - (CH2) 3-OC2H5
3 3rd
H5C6-O-CH2-CH2- H5C6-O-CH2-CH2-
2- 2-
—C3H7/C4H9/—C3H6—OC4H9 1:1:2 —C3H7 / C4H9 / —C3H6 — OC4H9 1: 1: 2
4 4th
H5C6-O-CH2-CH2- H5C6-O-CH2-CH2-
2- 2-
-C4H9 -C4H9
5 5
HsCe-GHa- HsCe-GHa-
2- 2-
-C4H9 -C4H9
6 6
H5C6—CH2— H5C6 — CH2—
3- 3-
-C4H9 -C4H9
7 7
H5C6—OC2H4 H5C6-OC2H4
3— 3—
-CH3 -CH3
8 8th
H5C6-OC2H4 H5C6-OC2H4
3— 3—
-C2H5 -C2H5
9 9
H5C6—OC2H4 H5C6-OC2H4
3- 3-
-C3H7 -C3H7
10 10th
H5C6-OC2H4-O-C2H4- H5C6-OC2H4-O-C2H4-
3- 3-
-CH3 -CH3
4 4th
5 5
10 10th
15 15
20 20th
25 25th
30 30th
35 35
40 40
45 45
50 50
55 55
60 60
65 65
CH 684 597 A5 CH 684 597 A5
Die Farbstoffe der Tabelle 2 entsprechen der Formel II' The dyes in Table 2 correspond to the formula II '
«Wz" "Wz"
di-) di-)
Farbstoff No. Dye No.
Cl u -jpcr Cl u -jpcr
12 R- -fji-CjHj 12 R- -fji-CjHj
14 R= 14 R =
13 R= 13 R =
XX XX
H H
Die Farbstoffe der Tabelle 3 entsprechen der Formel III' The dyes in Table 3 correspond to the formula III '
../R6 ../R6
NC _ NC _
CH„ CH "
xch2ch2-o-r7 xch2ch2-o-r7
(iii') (iii ')
5 5
5 5
10 10th
15 15
20 20th
25 25th
30 30th
35 35
40 40
45 45
50 50
55 55
CH 684 597 A5 CH 684 597 A5
Tabelle 3 Table 3
Farbstoff No. R6 Dye No. R6
r7 r7
15 -c4h9 15 -c4h9
16 16
17 17th
18 18th
19 19th
-c2h5 -c2h5
—CHjCHîCgHs do. do. —CHjCHîCgHs do. do.
-CO-NH-^^-Cl Cl -CO-NH - ^^ - Cl Cl
Cl Cl
~0~(ï} ~ 0 ~ (ï}
-co-(-ch2 )4-co-o-c2h4-:n -co - (- ch2) 4-co-o-c2h4-: n
/h2ch2c6h5 / h2ch2c6h5
V^Vch3 V ^ Vch3
>CN cn > CN cn
20 20th
nc nc
\ \
c=ch c = ch
NC' NC '
CH2CH20-C0-NHC6H5 CH2CH20-C0-NHC6H5
In den folgenden Beispielen bedeuten die Teile Gewichtsteile und die Prozente Gewichtsprozente; die Temperaturen sind in Celsiusgraden angegeben. Ein Volumenteil entspricht dem Volumen eines Gewichtsteiles Wasser. In the following examples, parts are parts by weight and percentages are percentages by weight; the temperatures are given in degrees Celsius. One part by volume corresponds to the volume of one part by weight of water.
6 6
5 5
10 10th
15 15
20 20th
25 25th
30 30th
35 35
40 40
45 45
50 50
55 55
60 60
65 65
CH 684 597 A5 CH 684 597 A5
Beispiel 1 example 1
16,5 T. des Farbstoffes No. 3 der Formel cooch2CH2OC6H5 16.5 T. of dye No. 3 of the formula cooch2CH2OC6H5
n = n n = n
- 0h„ ,cn - 0h ", cn
5,8 T. des Farbstoffes No. 11 der Formel 5.8 T. of dye No. 11 of the formula
R= H/CH3/O-C4H9 (1:1:2) R = H / CH3 / O-C4H9 (1: 1: 2)
(C2H5)2N- (C2H5) 2N-
und and
7,7 T. des Farbstoffes No. 15 der Formel 7.7 T. of dye No. 15 of the formula
NC C4H9 NC C4H9
C=CM-/^-N^ C = CM - / ^ - N ^
NC CH2 CH2 O-CO-NH—^^\-Cl NC CH2 CH2 O-CO-NH - ^^ \ - Cl
CH3 \=/ CH3 \ = /
Cl werden in Form ihres Presskuchens (Basis 100% Farbstoff) mechanisch gemischt. Aus der resultierenden Mischung stellt man durch wässrige Mahlung mit 70 T. eines Dispergators auf Ligninsulfonat-Basis nach bekannter Methode eine ultradispere Farbstoffmischung mit einer mittleren Partikelgrösse von 1 um und einem Coupageverhältnis von 3,0:10 her. Cl are mechanically mixed in the form of their press cake (based on 100% dye). From the resulting mixture, an ultradispere dye mixture with an average particle size of 1 μm and a coupling ratio of 3.0: 10 is produced by aqueous grinding with 70 parts of a dispersant based on lignin sulfonate using a known method.
8,0 Teile dieser Färbepräparation trägt man in 2000 Teile entmineralisiertes Wasser von 60°, das 40 Teile Ammoniumsulfat enthält, ein. Mit 85%-iger Ameisensäure wird der pH-Wert des Färbebades auf 5 eingestellt. In dieses Färbebad von ca. 60° gibt man 100 Teile gereinigtes Polyesterfasergewebe, schliesst die Apparatur, erhitzt im Verlaufe von 40 Minuten auf 130° und färbt weitere 60 Minuten bei dieser Temperatur. Nach dem Abkühlen auf 40° wird das Polyesterfasergewebe aus dem Färbebad genommen, gespült, geseift und mit Natriumhydrosulfit in üblicher Weise reduktiv nachgereinigt. Man erhält eine reine grünstichig gelbe Färbung mit sehr guten Allgemeinechtheiten. 8.0 parts of this dyeing preparation are introduced into 2000 parts of demineralized water at 60 °, which contains 40 parts of ammonium sulfate. The pH of the dyebath is adjusted to 5 using 85% formic acid. 100 parts of cleaned polyester fiber fabric are placed in this dyebath of approximately 60 °, the apparatus is closed, heated to 130 ° in the course of 40 minutes and dyed at this temperature for a further 60 minutes. After cooling to 40 °, the polyester fiber fabric is removed from the dyebath, rinsed, soaped and reductively cleaned in the usual manner with sodium hydrosulfite. A pure greenish yellow color with very good general fastness properties is obtained.
Beispiel 2 Example 2
Ersetzt man den Farbstoff No. 3 in Bsp. 1 durch 18 Teile des Farbstoffes No. 7 der Formel If you replace dye No. 3 in Example 1 by 18 parts of dye No. 7 of the formula
7 7
5 5
10 10th
15 15
20 20th
25 25th
30 30th
35 35
40 40
45 45
50 50
55 55
CH 684 597 A5 CH 684 597 A5
und verfährt ansonsten wie in Bsp. 1 beschrieben, so erhält man ebenfalls eine reine grünstichig gelbe Färbung mit sehr guten Allgemeinechtheiten. and otherwise proceeds as described in Example 1, a pure greenish yellow color with very good general fastness properties is also obtained.
Ähnlich günstige Ergebnisse werden erhalten, wenn man analog den voranstehenden Beispielen, die in der folgenden Tabelle 4 aufgeführten Farbstoffe vom Typus (l')-(lll') aus den Tabellen 1, 2 und 3 mischt. Similar favorable results are obtained if, analogously to the preceding examples, the dyes of the type (1 ') - (III') from Tables 1, 2 and 3 listed in Table 4 below are mixed.
Tabelle 4 Table 4
Bsp. No. Example No.
Farbstoff Typus I' (No., Teile) Dye type I '(No., parts)
Farbstoff Typus II' (No., Teile) Dye type II '(No., parts)
Farbstoff Typus III' (No., Teile) Dye type III '(No., parts)
Nuance auf PES Nuance on PES
3 3rd
No. 3 No. 3rd
19.5 T 19.5 d
No. 11, 7.5 T No. 11, 7.5 T.
No. 15, 3.0 T No. 15, 3.0 T.
grünst.gelb green-yellow
4 4th
No. 1 No. 1
17.0 T 17.0 d
No. 11, 6.0 T No. 11, 6.0 T.
No. 15, 7.0 T No. 15, 7.0 T
grünst.gelb green-yellow
5 5
No. 2 No. 2nd
16.0 T 16.0 d
No. 11, 6.5 T No. 11, 6.5 T.
No. 15, 7.5 T No. 15, 7.5 T.
grünstgelb greenish yellow
6 6
No. 6 No. 6
16.5 T 16.5 d
No. 11, 6.0 T No. 11, 6.0 T.
No. 15, 7.5 T No. 15, 7.5 T.
grünstgelb greenish yellow
7 7
No. 8 No. 8th
16.5 T 16.5 d
No. 11, 6.0 T No. 11, 6.0 T.
No. 15, 7.5 T No. 15, 7.5 T.
grünstgelb greenish yellow
8 8th
No. 9 No. 9
17.0 T 17.0 d
No. 11, 6.0 T No. 11, 6.0 T.
No. 15, 7.0 T No. 15, 7.0 T
grünstgelb g green yellow g
No.10 No.10
17.5 T 17.5 d
No. 11, 6.5 T No. 11, 6.5 T.
No. 15, 6.0 T No. 15, 6.0 T.
grünstgelb greenish yellow
10 10th
No. 3 No. 3rd
18.5 T 18.5 d
No. 11, 7.0 T No. 11, 7.0 T
No. 16, 4.5 T No. 16.4.5 T.
grünstgelb greenish yellow
11 11
No. 7 No. 7
18.5 T 18.5 d
No. 11, 7.0 T No. 11, 7.0 T
No. 16, 4.5 T No. 16.4.5 T.
grünstgelb greenish yellow
12 12th
No. 3 No. 3rd
18.5 T 18.5 d
No. 11, 7.0 T No. 11, 7.0 T
No. 17, 4.5 T No. 17, 4.5 T.
grünstgelb greenish yellow
13 13
No. 7 No. 7
18.5 T 18.5 d
No. 11, 7.0 T No. 11, 7.0 T
No. 17, 4.5 T No. 17, 4.5 T.
grünstgelb greenish yellow
14 14
No. 3 No. 3rd
17.5 T 17.5 d
No. 11, 7.0 T No. 11, 7.0 T
No. 18, 5.5 T No. 18, 5.5 d
grünstgelb greenish yellow
15 15
No. 7 No. 7
17.5 T 17.5 d
No. 11, 7.0 T No. 11, 7.0 T
No. 18, 5.5 T No. 18, 5.5 d
grünstgelb greenish yellow
16 16
No. 3 No. 3rd
18.5 T 18.5 d
No. 11, 7.0 T No. 11, 7.0 T
No. 19, 4.5 T No. 19, 4.5 d
grünst.gelb green-yellow
17 17th
No. 7 No. 7
18.5 T 18.5 d
No. 11, 7.0 T No. 11, 7.0 T
No. 19, 4.5 T No. 19, 4.5 d
grünstgelb greenish yellow
18 18th
No. 3 No. 3rd
17.0 T 17.0 d
No. 11, 6.5 T No. 11, 6.5 T.
No. 20, 6.5 T No. 20, 6.5 T.
grünstgelb ig greenish yellow
No. 7 No. 7
17.0 T 17.0 d
No. 11, 6.5 T No. 11, 6.5 T.
No. 20, 6.5 T No. 20, 6.5 T.
grünstgelb greenish yellow
20 20th
No. 7 No. 7
18.5 T 18.5 d
No. 11, 7.0 T No. 11, 7.0 T
No. 21, 4.5 T No. 21, 4.5 T.
grünstgelb greenish yellow
21 21
No. 3 No. 3rd
17.0 T 17.0 d
No. 12, 5.5 T No. 12, 5.5 T.
No. 15, 7.5 T No. 15, 7.5 T.
grünstgelb greenish yellow
22 22
No. 7 No. 7
17.0 T 17.0 d
No. 12, 5.5 T No. 12, 5.5 T.
No. 15, 7.5 T No. 15, 7.5 T.
grünstgelb greenish yellow
23 23
No. 3 No. 3rd
17.0 T 17.0 d
No. 13, 5.5 T No. 13, 5.5 T.
No. 15, 7.5 T No. 15, 7.5 T.
grünstgelb greenish yellow
24 24th
No. 7 No. 7
17.0 T 17.0 d
No. 13, 5.5 T No. 13, 5.5 T.
No. 15, 7.5 T No. 15, 7.5 T.
grünstgelb greenish yellow
25 25th
No. 3 No. 3rd
17.0 T 17.0 d
No. 14, 5.5 T No. 14.5.5 T.
No. 15, 7.5 T No. 15, 7.5 T.
grünstgelb greenish yellow
26 26
No. 7 No. 7
17.0 T 17.0 d
No. 14, 5.5 T No. 14.5.5 T.
No. 15, 7.5 T No. 15, 7.5 T.
grünstgelb greenish yellow
27 27
No. 3 No. 3rd
22.5 T 22.5 d
No. 11, 7.5 T No. 11, 7.5 T.
- -
grünstgelb greenish yellow
28 28
No. 3 No. 3rd
24.0 T 24.0 d
No. 11, 6.0 T No. 11, 6.0 T.
- -
grünstgelb greenish yellow
2g 2g
No. 7 No. 7
24.0 T 24.0 d
No. 11, 6.0 T No. 11, 6.0 T.
- -
grünstgelb greenish yellow
30 30th
No. 7 No. 7
24.0 T 24.0 d
No. 11, 6.0 T No. 11, 6.0 T.
- -
grünstgelb greenish yellow
31 31
No. 7 No. 3 No. 7 No. 3rd
12.0 T 12.0 T 12.0 D 12.0 D
No. 11, 6.0 T No. 11, 6.0 T.
— -
grünstgelb greenish yellow
32 32
No. 7 No. 7
20.0 T 20.0 d
No. 13, 5.0 T No. 13, 5.0 T.
No. 17, 5.0 T No. 17, 5.0 T.
grünstgelb greenish yellow
33 33
No. 7 No. 7
20.0 T 20.0 d
No. 12, 5.0 T No. 12, 5.0 T.
No. 17, 5.0 T No. 17, 5.0 T.
grünstgelb greenish yellow
34 34
No. 1 No. 2 No. 1 No. 2nd
9.0 T 9.0 T 9.0 D 9.0 D
No. 11, 6.5 T No. 11, 6.5 T.
No. 15, 5.5 T No. 15, 5.5 T.
grünstgelb greenish yellow
35 35
No. 3 No. 3rd
16.0 T 16.0 d
No. 11, 10.0 T No. 11, 10.0 T.
No. 15, 4.0 T No. 15.4.0 T
grünstgelb greenish yellow
36 36
No. 7 No. 7
16.0 T 16.0 d
No. 11, 10.0 T No. 11, 10.0 T.
No. 15, 4,0 T No. 15, 4.0 T.
grünstgelb greenish yellow
8 8th
5 5
10 10th
15 15
20 20th
25 25th
30 30th
35 35
40 40
45 45
50 50
55 55
60 60
65 65
CH 684 597 A5 CH 684 597 A5
Beispiel 37 Example 37
26,5 Teile Anthranilsäure-ß-phenoxyäthylester (97%) werden in 70 Teilen Eisessig von 45° klar gelöst und mit 31 Teilen Salzsäure (36,5%) und 200 Teilen Eiswasser vesetzt; die resultierende Suspension wird bei 0-5° mit 7,2 Teilen Natriumnitrit, in Form einer 5n-Lösung, wie üblich diazotiert. Nach Zerstörung der überschüssigen salpetrigen Säure mit Aminosulfonsäure wird die klärfiltrierte Diazoniumsalzlö-sung bei 5-10° zu einer Lösung enthaltend 11,0 Teile der Kupplungskomponente der Formel a und 13,9 Teile der Kupplungskomponente der Formel b ch, cn 26.5 parts of anthranilic acid-β-phenoxyethyl ester (97%) are clearly dissolved in 70 parts of glacial acetic acid at 45 ° and mixed with 31 parts of hydrochloric acid (36.5%) and 200 parts of ice water; the resulting suspension is diazotized at 0-5 ° with 7.2 parts of sodium nitrite in the form of a 5N solution, as usual. After the excess nitrous acid has been destroyed with aminosulfonic acid, the clarified-filtered diazonium salt solution is at 5-10 ° to a solution containing 11.0 parts of the coupling component of the formula a and 13.9 parts of the coupling component of the formula b ch, cn
(a) (a)
0h (ch2)3—ch3 0h (ch2) 3-ch3
(ch2)3-oc4h9 (ch2) 3-oc4h9
(b) (b)
10 Teile Eisessig und 400 Teile Eiswasser, unter gutem Rühren bei pH 4-5 zulaufen gelassen. Der pH-Wert wird durch Zugabe von Natronlauge (30%) im Bereich von 4-5 konstant gehalten. Die resultierende gelbe Suspension wird abfiltriert, mit 1000 Teilen Wasser von 50° säurefrei gewaschen und der Farbstoff im Vakuum bei 40° getrocknet. Zur weiteren Reinigung kann das Farbstoffgemisch z.B. aus Cellosolve als Lösungsmittel umkristallisiert werden. 10 parts of glacial acetic acid and 400 parts of ice water, run in at pH 4-5 with good stirring. The pH is kept constant in the range of 4-5 by adding sodium hydroxide solution (30%). The resulting yellow suspension is filtered off, washed with 1000 parts of water at 50 ° free of acid and the dye is dried in vacuo at 40 °. For further cleaning, the dye mixture can e.g. be recrystallized from cellosolve as a solvent.
Man erhält auf diese Weise ein Farbstoff-Gemisch der Formel c, This gives a dye mixture of the formula c
och2ch2oc6h5 och2ch2oc6h5
(c) (c)
R2 m —CH3/—OC4H9—n *** lsl >W.(DMF) - 431 nm das PES-Fasern in grünstichig-gelber Nuance mit sehr guten Allgemeinechtheiten färbt. In der folgenden Tabelle 5 sind weitere Farbstoff-Gemische der Formel la' R2 m —CH3 / —OC4H9 — n *** lsl> W. (DMF) - 431 nm which dyes PES fibers in a greenish-yellow shade with very good general fastness properties. Table 5 below shows further dye mixtures of the formula Ia '
(la') (la ')
oh (ch2)m—r2' oh (ch2) m — r2 '
angegeben, specified
worin R5 in allen Fällen Wasserstoff bedeutet, ausgenommen im 1. Farbstoff des Beispiels 51, für welchen R5 Methyl in 5'-Steliung ist. wherein R5 is hydrogen in all cases, except in the 1st dye of Example 51, for which R5 is methyl in 5 'position.
Diese Farbstoff-Gemische lassen sich analog zur Arbeitsvorschrift des Beispiels 1 herstellen, können aber gleich gut statt durch Mischkupplung auch durch nachträgliches Mischen der Einzelkomponenten hergestellt werden. These dye mixtures can be prepared analogously to the working procedure of Example 1, but can also be produced equally well instead of by a mixing coupling by subsequently mixing the individual components.
9 9
5 5
10 10th
15 15
20 20th
25 25th
30 30th
35 35
40 40
45 45
50 50
55 55
60 60
65 65
CH 684 597 A5 CH 684 597 A5
Tabelle 5 Table 5
Bsp. E.g.
FV FV
% %
R4 (Stellung) R4 (position)
m m
>-max- (nm) > -max- (nm)
Nr. No.
(DMF) (DMF)
38 38
-OC3H7 -OC3H7
50 50
H H
3 3rd
431 431
-OC2H5 -OC2H5
50 50
H H
3 3rd
39 39
-OC3H7 -OC3H7
50 50
H H
3 3rd
431 431
-OC3H7-Ì -OC3H7-Ì
50 50
H H
3 3rd
40 40
-OC4H9 -OC4H9
50 50
H H
3 3rd
431 431
—OC4H9—i -OC4H9-i
50 50
H H
3 3rd
41 41
-OC2H5 -OC2H5
35 35
H H
3 3rd
431 431
-OC3H7 -OC3H7
30 30th
H H
3 3rd
-OC4H9 -OC4H9
35 35
H H
3 3rd
42 42
-OC4H9 -OC4H9
65 65
H H
3 3rd
431 431
-OC6Hi3 -OC6Hi3
35 35
H H
3 3rd
43 43
-OC2H5 -OC2H5
40 40
H H
3 3rd
431 431
-OC4H9 -OC4H9
40 40
H H
3 3rd
—CHs —CHs
20 20th
H H
3 3rd
44 44
-OC3H7 -OC3H7
50 50
H H
3 3rd
431 431
-OC4H9 -OC4H9
50 50
H H
3 3rd
45 45
-OC2H5 -OC2H5
40 40
H H
3 3rd
431 431
-OC4H9 -OC4H9
40 40
H H
3 3rd
—OC4H9—i -OC4H9-i
20 20th
H H
3 3rd
46 46
-OC2H5 -OC2H5
40 40
H H
3 3rd
431 431
-OC3H7 -OC3H7
10 10th
H H
3 3rd
-OC4H9 -OC4H9
40 40
H H
3 3rd
—OC4H9—i -OC4H9-i
10 10th
H H
3 3rd
47 47
-OC2H5 -OC2H5
50 50
H H
2 2nd
431 431
-OC4H9 -OC4H9
50 50
H H
2 2nd
48 48
-OC2H5 -OC2H5
30 30th
—CH3(4') —CH3 (4 ')
3 3rd
431 431
-OC4H9 -OC4H9
70 70
H H
3 3rd
49 49
-OC2H5 -OC2H5
30 30th
-Cl (4') -Cl (4 ')
3 3rd
431 431
-OC4H9 -OC4H9
70 70
H H
50 50
-OC2H5 -OC2H5
30 30th
-OCH3(4') -OCH3 (4 ')
3 3rd
431 431
-OC4H9 -OC4H9
70 70
H H
3 3rd
51 51
-OC2H5 -OC2H5
20 20th
-CH3(2') -CH3 (2 ')
3 3rd
431 431
-OG4H9 -OG4H9
80 80
H H
3 3rd
52 52
-OC2H5 -OC2H5
25 25th
H H
3 3rd
431 431
-OC4H9 -OC4H9
25 25th
H H
3 3rd
-ch3 -ch3
50 50
H H
3 3rd
53 53
-OC4H9 -OC4H9
50 50
H H
3 3rd
431 431
-CHs -CHs
50 50
H H
3 3rd
54 54
-OC4H9 -OC4H9
50 50
H H
2 2nd
431 431
-ch3 -ch3
25 25th
H H
2 2nd
-ch3 -ch3
25 25th
H H
3 3rd
55 55
-OC2H5 -OC2H5
25 25th
H H
3 3rd
431 431
-OC4H9 -OC4H9
25 25th
H H
3 3rd
-CH3 -CH3
25 25th
H H
2 2nd
-CH3 -CH3
25 25th
H H
3 3rd
56 56
-OCH3 -OCH3
25 25th
H H
3 3rd
431 431
-OC2H5 -OC2H5
25 25th
H H
3 3rd
-CHs -CHs
50 50
H H
3 3rd
10 10th
5 5
10 10th
15 15
20 20th
25 25th
30 30th
35 35
40 40
45 45
50 50
55 55
60 60
65 65
CH 684 597 A5 CH 684 597 A5
Beispiel 57 Example 57
24,8 Teile Anthranilsäure-benzylester (98%) werden in 100 Teilen Eisessig von 45° klar gelöst und mit 35 Teilen Salzsäure (36,5%) und 150 Teilen Eiswasser versetzt; die resultierende Suspension wird bei 0-5° mit 7,2 Teilen Natriumnitrit, in Form einer 5n-Lösung, wie üblich diazotiert. Nach Zerstörung der überschüssigen salpetrigen Säure mit Aminosulfonsäure wird die klärfiltrierte Diazoniumsalzlösung bei 5-10° zu einer Lösung enthaltend 22,5 Teile der Kupplungskomponente der Formel d und 2,8 Teile der Kupplungskomponente der Formel e, 24.8 parts of benzyl anthranilate (98%) are clearly dissolved in 100 parts of glacial acetic acid at 45 ° and mixed with 35 parts of hydrochloric acid (36.5%) and 150 parts of ice water; the resulting suspension is diazotized at 0-5 ° with 7.2 parts of sodium nitrite in the form of a 5N solution, as usual. After the excess nitrous acid has been destroyed with aminosulfonic acid, the clarified, filtered diazonium salt solution at 5-10 ° to a solution containing 22.5 parts of the coupling component of the formula d and 2.8 parts of the coupling component of the formula e,
ch3 cn ch3 cn
(d) (d)
(ch2)3— oc2h5 (ch2) 3— oc2h5
ch3 cn ch3 cn
Ôr oh > Ohr oh>
(e) (e)
(ch2)3— oc4h9 (ch2) 3—oc4h9
10 Teile Eisessig und 400 Teile Eiswasser unter gutem Rühren bei pH 4-5 zulaufen gelassen. Der pH-Wert wird durch Zugabe von Natronlauge (30%) im Bereich von 4-5 konstant gehalten. Die resultierende gelbe Suspension wird abfiltriert, mit 1000 Teilen Wasser von 50° säurefrei gewaschen und der Farbstoff im Vakuum bei 40° getrocknet. Zur weiteren Reinigung kann das Farbstoff-Gemisch z.B. aus Cellosolve als Lösungsmittel umkristallisiert werden. 10 parts of glacial acetic acid and 400 parts of ice water were run in at pH 4-5 with good stirring. The pH is kept constant in the range of 4-5 by adding sodium hydroxide solution (30%). The resulting yellow suspension is filtered off, washed with 1000 parts of water at 50 ° free of acid and the dye is dried in vacuo at 40 °. For further cleaning, the dye mixture can e.g. be recrystallized from cellosolve as a solvent.
Man erhält auf diese Weise ein Farbstoff-Gemisch der Formel f, This gives a dye mixture of the formula f
OCHoCcHç = -0C2H5/-0C4H9-n'^9:l OCHoCcHç = -0C2H5 / -0C4H9-n '^ 9: l
I 2 b j I 2 b j
CO CH3 CN CO CH3 CN
r-j w x«.x.(DMF) » 432 nm r-j w x «.x. (DMF)» 432 nm
// \\_N=N__/ )=0 // \\ _ N = N __ /) = 0
W " " V/ W "" V /
OH OH
(CH2)3-R2' (CH2) 3-R2 '
das PES-Fasern in grünstichig-gelber Nuance mit sehr guten Allgemeinechtheiten färbt. that dyes PES fibers in a greenish-yellow shade with very good general fastness properties.
In der folgenden Tabelle 6 sind weitere Farbstoff-Gemische angegeben, sie entsprechen der Formel la", Further dye mixtures are given in the following Table 6, they correspond to the formula Ia ",
für welche in Tabelle 6 die Variablen angeführt sind. for which the variables are listed in Table 6.
Diese Farbstoff-Gemische lassen sich analog zur Arbeitsvorschrift des Beispiels 37 herstellen, können aber gleich gut statt durch Mischkupplung auch durch nachträgliches Mischen der Einzelkomponenten gewonnen werden. These dye mixtures can be prepared analogously to the working procedure of Example 37, but can equally well be obtained by subsequently mixing the individual components instead of by mixing coupling.
11 11
5 5
10 10th
15 15
20 20th
25 25th
30 30th
35 35
40 40
45 45
50 50
55 55
CH 684 597 A5 CH 684 597 A5
Tabelle 6 Table 6
Bsp. Nr. Example No.
R2' R2 '
% %
R4 (Stellung) R4 (position)
m m
Âmax- (nm) Âmax- (nm)
(DMF) (DMF)
58 58
-OC2H5 -OC2H5
70 70
H H
3 3rd
432 432
-OC4H9 -OC4H9
30 30th
H H
3 3rd
59 59
-OC3H7 -OC3H7
50 50
H H
3 3rd
432 432
—OC3H7—i -OC3H7-i
50 50
H H
3 3rd
60 60
-OC4H9 -OC4H9
50 50
H H
3 3rd
432 432
—OC4H9—i -OC4H9-i
50 50
H H
3 3rd
61 61
-OC2H5 -OC2H5
35 35
H H
3 3rd
432 432
-OC3H7 -OC3H7
25 25th
H H
3 3rd
-OC4H9 -OC4H9
40 40
H H
3 3rd
62 62
—OC4H9 —OC4H9
66 66
H H
3 3rd
432 432
—OC6H13 —OC6H13
35 35
H H
3 3rd
63 63
-OC2H5 -OC2H5
40 40
H H
3 3rd
432 432
-OC4H9 -OC4H9
40 40
H H
3 3rd
-CH3 -CH3
20 20th
H H
3 3rd
64 64
-OC2H5 -OC2H5
30 30th
H H
3 3rd
432 432
-OC4H9 -OC4H9
30 30th
H H
3 3rd
-ch3 -ch3
20 20th
H H
3 3rd
-C3H7 -C3H7
20 20th
H H
3 3rd
65 65
-OG2H5 -OG2H5
40 40
H H
3 3rd
432 432
—OG4H9—i —OG4H9 — i
20 20th
H H
3 3rd
-OC4H9 -OC4H9
40 40
H H
3 3rd
66 66
-OC2H5 -OC2H5
40 40
H H
3 3rd
432 432
-OC3H7 -OC3H7
10 10th
H H
3 3rd
—OC4H9—i -OC4H9-i
40 40
H H
3 3rd
-OC4H9 -OC4H9
10 10th
H H
3 3rd
67 67
—OC2H5 —OC2H5
50 50
H H
2 2nd
431 431
-OC4H9 -OC4H9
50 50
H H
2 2nd
68 68
—OC2H5 —OC2H5
85 85
4'-CHs 4'-CHs
3 3rd
432 432
-OC4H9 -OC4H9
15 15
4'-CH3 4'-CH3
3 3rd
69 69
—OC2H5 —OC2H5
85 85
4'-CI 4'-CI
3 3rd
433 433
-OC4H9 -OC4H9
15 15
4'-CI 4'-CI
3 3rd
70 70
-OC2H5 -OC2H5
90 90
H H
3 3rd
432 432
-OCH3 -OCH3
10 10th
H H
3 3rd
71 71
-OC2H5 -OC2H5
50 50
H H
3 3rd
432 432
-CH3 -CH3
50 50
H H
3 3rd
72 72
-OC2H5 -OC2H5
70 70
H H
3 3rd
432 432
-CHs -CHs
30 30th
H H
3 3rd
73 73
-OC2H5 -OC2H5
60 60
H H
3 3rd
432 432
-CHs -CHs
20 20th
H H
2 2nd
-CHs -CHs
20 20th
H H
3 3rd
74 74
-OCH3 -OCH3
50 50
H H
3 3rd
432 432
-OC2H5 -OC2H5
50 50
H H
3 3rd
75 75
-OCH3 -OCH3
20 20th
H H
3 3rd
432 432
-OC2H5 -OC2H5
80 80
H H
3 3rd
12 12th
5 5
10 10th
15 15
20 20th
25 25th
30 30th
35 35
40 40
45 45
50 50
55 55
60 60
65 65
CH 684 597 A5 CH 684 597 A5
ANWENDUNGSBEISPIEL APPLICATION EXAMPLE
Das gemäss Beispiel 1 erhaltene Farbstoff-Gemisch wird mittels Sandmahlung in Gegenwart von Dispergatoren, z.B. handelsüblichem Ligninsulfonat, und anschliessender Zerstäubung in ein ultradisperses Färbepräparat der mittleren Partikelgrösse 1 [im und einem Coupageverhältnis von 3,5:10 übergeführt. The dye mixture obtained according to Example 1 is ground by sand grinding in the presence of dispersants, e.g. commercial lignin sulfonate, and subsequent atomization into an ultradisperse dye preparation of average particle size 1 [im and a coupage ratio of 3.5: 10.
12 Teile dieses Präparats werden mit 1000 Teilen Wasser andispergiert und der zirkulierenden Flotte (13 000 Teile, enthaltend 30 Teile Ammonsulfat und 0,3 Teile Ameisensäure als Puffer und gegebenenfalls eine Carrier-/Egalisiermittel-Kombination) bei 60° zugefügt. Die vorgereinigte, gepresste Kreuzspule (1000 Teile Polyestergarn auf Plastikhülse) wird eingebracht, der Färbeautoklav verschlossen und in 35 Minuten auf 130° erhitzt. Nach 90 Minuten wird auf 80° gekühlt, die ausgezogene Flotte abgelassen und das so gefärbte Substrat mit kaltem Wasser gründlich gewaschen und auf übliche Weise reduktiv nachgereinigt. Sodann wird abgeschwungen und getrocknet. Man erhält eine egale, reine gelbe Färbung. 12 parts of this preparation are dispersed with 1000 parts of water and added to the circulating liquor (13,000 parts, containing 30 parts of ammonium sulfate and 0.3 part of formic acid as a buffer and optionally a carrier / leveling agent combination) at 60 °. The pre-cleaned, pressed cross-wound bobbin (1000 parts of polyester yarn on a plastic sleeve) is inserted, the dyeing autoclave is closed and heated to 130 ° in 35 minutes. After 90 minutes, the mixture is cooled to 80 °, the extracted liquor is drained off and the substrate colored in this way is thoroughly washed with cold water and reductively cleaned in the customary manner. Then it is swung and dried. A level, pure yellow color is obtained.
Claims (3)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4137822 | 1991-11-16 | ||
| DE4201539 | 1992-01-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH684597A5 true CH684597A5 (en) | 1994-10-31 |
Family
ID=25909235
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH3507/92A CH684597A5 (en) | 1991-11-16 | 1992-11-13 | Mixtures of dispersion dyes. |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPH06100793A (en) |
| CH (1) | CH684597A5 (en) |
| DE (1) | DE4238231A1 (en) |
| ES (1) | ES2065237B1 (en) |
| FR (1) | FR2683822B1 (en) |
| GB (1) | GB2261439B (en) |
| IT (1) | IT1263025B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19512424A1 (en) * | 1995-04-03 | 1996-10-10 | Bayer Ag | Green disperse dye mixtures |
| CN103073918B (en) * | 2013-01-21 | 2014-10-15 | 江苏亚邦染料股份有限公司 | Medium temperature type three-primary-color disperse dyes |
| CN105541852B (en) * | 2016-01-29 | 2017-09-15 | 扬州大学 | 2‑（The base of cumarin 3）The synthetic method of 6 picolines simultaneously [5,4 C] cumarin |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1594324A (en) * | 1968-07-08 | 1970-06-01 | ||
| DE1917278B2 (en) * | 1969-04-03 | 1974-06-27 | Basf Ag, 6700 Ludwigshafen | Monoazo dyes, processes for their production and dye preparations |
| CH1678672A4 (en) * | 1969-04-18 | 1974-10-15 | ||
| BE795380A (en) * | 1972-02-15 | 1973-08-13 | Sandoz Sa | NEW HETEROCYCLIC COMPOUNDS LOW WATER SOLUBLE, THEIR PREPARATION AND THEIR USE AS COLORANTS |
| GB1543933A (en) * | 1975-07-02 | 1979-04-11 | Basf Ag | Dyes of the coumarin series |
| DE2739841C2 (en) * | 1977-09-03 | 1979-10-25 | Bayer Ag, 5090 Leverkusen | Transfer printing process |
| DE3012863A1 (en) * | 1980-04-02 | 1981-10-08 | Cassella Ag, 6000 Frankfurt | DYE MIXTURE, METHOD FOR THEIR PRODUCTION, DYES CONTAINING IT AND METHOD FOR COLORING AND PRINTING SYNTHETIC, HYDROPHOBIC FIBER MATERIAL |
| US4548613A (en) * | 1984-05-18 | 1985-10-22 | American Hoechst Corporation | Yellow disperse dyestuff mixtures and dyeing process |
| DE3736817A1 (en) * | 1987-10-30 | 1989-05-11 | Basf Ag | PYRIDONAZO DYES AND THEIR USE |
| US5038415A (en) * | 1989-01-10 | 1991-08-13 | Sumitomo Chemical Company, Limited | Disperse dye composition useful for dyeing of printing hydrophobic fiber materials: mixture of pyridone mono-azo dyes and optionally a quino-phthalone |
-
1992
- 1992-11-10 FR FR9213650A patent/FR2683822B1/en not_active Expired - Fee Related
- 1992-11-12 IT ITRM920823A patent/IT1263025B/en active IP Right Grant
- 1992-11-12 GB GB9223700A patent/GB2261439B/en not_active Expired - Fee Related
- 1992-11-12 DE DE4238231A patent/DE4238231A1/de not_active Withdrawn
- 1992-11-13 ES ES09202300A patent/ES2065237B1/en not_active Expired - Lifetime
- 1992-11-13 CH CH3507/92A patent/CH684597A5/en not_active IP Right Cessation
- 1992-11-13 JP JP4303442A patent/JPH06100793A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| GB2261439B (en) | 1995-02-08 |
| DE4238231A1 (en) | 1993-05-19 |
| GB9223700D0 (en) | 1992-12-23 |
| ITRM920823A1 (en) | 1994-05-12 |
| IT1263025B (en) | 1996-07-23 |
| ES2065237A1 (en) | 1995-02-01 |
| ITRM920823A0 (en) | 1992-11-12 |
| FR2683822B1 (en) | 1994-12-23 |
| JPH06100793A (en) | 1994-04-12 |
| GB2261439A (en) | 1993-05-19 |
| FR2683822A1 (en) | 1993-05-21 |
| ES2065237B1 (en) | 1995-10-01 |
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