GB2307479A - Monoazo dye mixtures based on 5-(4'-substituted-3'-nitrophenylazo)-N-substituted-3-cyano-4-methyl-6-hydroxypyrid-2-ones - Google Patents
Monoazo dye mixtures based on 5-(4'-substituted-3'-nitrophenylazo)-N-substituted-3-cyano-4-methyl-6-hydroxypyrid-2-ones Download PDFInfo
- Publication number
- GB2307479A GB2307479A GB9623772A GB9623772A GB2307479A GB 2307479 A GB2307479 A GB 2307479A GB 9623772 A GB9623772 A GB 9623772A GB 9623772 A GB9623772 A GB 9623772A GB 2307479 A GB2307479 A GB 2307479A
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- United Kingdom
- Prior art keywords
- formula
- substituted
- dye mixture
- dyes
- phenyl
- Prior art date
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- Granted
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- 239000000203 mixture Substances 0.000 title claims description 58
- -1 5-(4'-substituted-3'-nitrophenylazo)-N-substituted-3-cyano-4-methyl-6-hydroxypyrid-2-ones Chemical class 0.000 title claims description 8
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 title 1
- 239000000975 dye Substances 0.000 claims description 82
- 239000000463 material Substances 0.000 claims description 30
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 239000004753 textile Substances 0.000 claims description 15
- 238000004043 dyeing Methods 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 229920000728 polyester Polymers 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 239000000835 fiber Substances 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 230000002209 hydrophobic effect Effects 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- 230000008878 coupling Effects 0.000 claims description 4
- 238000010168 coupling process Methods 0.000 claims description 4
- 238000005859 coupling reaction Methods 0.000 claims description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000006232 ethoxy propyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000000243 solution Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 238000005406 washing Methods 0.000 description 6
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 5
- 239000004744 fabric Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- 239000002270 dispersing agent Substances 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
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 238000006193 diazotization reaction Methods 0.000 description 3
- 229920002284 Cellulose triacetate Polymers 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 2
- 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 2
- 239000002253 acid Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- 150000001989 diazonium salts Chemical class 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000000859 sublimation Methods 0.000 description 2
- 230000008022 sublimation Effects 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 229920002994 synthetic fiber Polymers 0.000 description 2
- NHCOOKBBGMCQFD-UHFFFAOYSA-N 2-nitro-4-phenoxyaniline Chemical compound C1=C([N+]([O-])=O)C(N)=CC=C1OC1=CC=CC=C1 NHCOOKBBGMCQFD-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
- QFMJFXFXQAFGBO-UHFFFAOYSA-N 4-methoxy-2-nitroaniline Chemical compound COC1=CC=C(N)C([N+]([O-])=O)=C1 QFMJFXFXQAFGBO-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 229920003043 Cellulose fiber Polymers 0.000 description 1
- 240000008886 Ceratonia siliqua Species 0.000 description 1
- 235000013912 Ceratonia siliqua Nutrition 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 239000001166 ammonium sulphate Substances 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000001044 red dye 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
- 238000005507 spraying Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 239000004758 synthetic textile Substances 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000002759 woven fabric Substances 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
- C09B67/0046—Mixtures of two or more azo dyes
- C09B67/0051—Mixtures of two or more azo dyes mixture of two or more monoazo dyes
-
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
- C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
- C09B29/3617—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom
- C09B29/3621—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring
- C09B29/3626—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring from a pyridine ring containing one or more hydroxyl groups (or = O)
- C09B29/363—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring from a pyridine ring containing one or more hydroxyl groups (or = O) from diazotized amino carbocyclic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Coloring (AREA)
Description
1-20647 Mixtures of monoazopyridone dyes 2307479 The present invention
relates to mixtures of monoazopyridone dyes, their preparation and their use for dyeing or printing textile fibre materials.
Monoazopyridone dyes and their use for dyeing synthetic fibre materials are known, for example, from EP-A-0 440 072. However, it has been found that these dyes do not always completely meet the highest demands. There is therefore a need for novel dyes or dye combinations which show, in particular, better exhaustion, build-up or wash-fastness properties.
It has now been found, surprisingly, that the mixtures according to the invention exhaust to a high degree on the fibres and are distinguished by a very good build-up and the resulting dyeings have good fastness to light, sublimation and washing.
The present invention thus relates to a dye mixture comprising at least two structurally different dyes, each of which has the formula N02 H3C CN Rio --- N = N 0 HO R, in which R, is Cl-C4alkyl and (1) R2 is isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl; or Cl- C3alkyl which is substituted by phenyl or phenoxy; or R, is phenyl which is unsubstituted or substituted by Cil-C4alkyl, Cl-C4alkoxy, hydroxyl or halogen; Cl-C4alkoxy-Cl-C3alkylene, phenoxy-Cl-C3a]kylene or Cl-C3alkyl which is substituted by phenyl which is unsubstituted or substituted by C11-CAlkyl, Cl-CAlkoxy, hydroxyl or halogen and R2 is Cl-Cloalkyl which is unsubstituted or substituted by hydroxyl, 0COR3 or phenoxy, where the phenyl ring in phenoxy is unsubstituted or substituted by C11-CAlkyl, ClC4alkoxy, hydroxyl or halogen and the alkyl chain in Cl-Cloalkyl from C3 can be interrupted by one or more oxygen atoms; phenyl which is unsubstituted or substituted by Cl-COlkyl, Cl-C4alkoxy, hydroxyl or halogen; or C5- C7CYcloalky]; and R3 is Cl-COlkyl.
Cl-C3alkyl in formula (1) is methyl, ethyl, isopropyl or n-propyl. ClC3alkylene in formula (1) is, for example, methylene, ethylene or propylene. Cl-C4alkyl in formula (1) is methyl, ethyl, isopropy], npropyl, isobuty], n-butyi, sec-butyl or tert-butyl. Cl-Cloalkyl in formula (1) can be, in addition to the radicals mentioned above for Cl- COlkyl, straight-chain or branched alkyl radicals, for example pentyl, hexy], octyl, nonyl or decyl. Cl-COlkoxy in formula (1) is methoxy, ethoxy, isopropoxy, propoxy, n-butoxy, isobutoxy, sec-butoxy or tert- butoxy.
CS-C7CYCloalkyl in formula (1) is, for example, cyclopentyl, cyclohexyl or cycloheptyl. Halogen in formula (1) is, for example, fluorine, bromine or, in particular, chlorine.
Preferred dye mixtures are those comprising dyes of the formula (1) in which R, is phenyl which is substituted by Cl-COlkyl, Cl-C4alkoxy, hydroxyl or halogen, or, preferably, methyl or unsubstituted phenyl.
The structurally different dyes in the dye mixtures according to the invention can in each case contain the same substituents R, and different substituents R2, or the same substituents R2 and different substituents IR,, or different substituents R, and R2.
Preferred dye mixtures are those which comprise two structurally different dyes of the formula (1). The ratio of the individual dyes in the dye mixtures according to the invention can vary within a wide range, for example from 1:1 up to 1:5. Dye mixtures which have a ratio of the two dyes of 1:1 to 1:3 are preferred. Dye mixtures which comprise the dyes in the ratio of 1:1 are particularly preferred.
The following dye mixtures of the structurally different dyes (A) and (B) of the formula (1) listed in Table 1 are particularly preferred:
Table 1
Dye (A) Dye (B) Dye mixture No. R, R2 R, R2 1 CH3 CH(C1-13)2 CH3 CH2CH(C1-13)2 2 CH3 CH(C1-13)2 CH3 (CH2)3CH3 3 CH3 CH(C1-13)2 CH3 CH(C1-13)CH2CH3 4 CH3 CH(C1-13)2 CH3 C(C1-13)3 CH3 (CH2)3CH3 CH3 CH2CH(CH3)2 6 CH3 (CHA3CH3 CH3 CH(C1-13)CH2CH3 7 CH3 (CH2)3CH3 CH3 C(C1-13)3 8 CH3 CH(C1-13)CH2CH3 CH3 CH2CH(CH3)2 9 CH3 CH2CH(CH3)2 CH3 C(CH3)3 CH3 CH(C1-13)CH2CH3 CH3 C(C1-13)3 11 C6H5 CH3 C6H5 (CH2)20CH3 12 C6H5 CH3 C6H5 (CH2)30CH3 13 C6H5 CH3 C6H5 (CH2)30CH2CH3 14 C6H5 CH3 C6H5 (CH2)30CH(CH3)2 C6H5 CH2CH3 C6H5 (CH2)20CH3 16 C6H5 CH2CH3 C6H5 (CH2)30CH3 17 C6H5 CH2CH3 C6H5 (CH2)30CH2CH3 18 C6H5 CH2CH3 C6H5 (CH2)30CH(CH3)2 19 CH3 (CH2)3CH3 C6H5 CH3 CH3 CH(C1-13)CH2CH3 C6H5 CH3 21 CH3 CH2CH(CH3)2 C6H5 CH3 22 CH3 C(C1-13)3 C6H5 CH3 23 CH3 CH(C1-13)2 C6H5 CH3 24 CH3 (CH2)3CH3 C6H5 CH2CH3 CH3 CH(C1-13)CH2CH3 C6H5 CH2CH3 The mixture comprising the dye of the formula (1) in which R, is methyl and R2 is n-butyi, the dye of the formula (1) in which R, is methyl and R2 is sec-butyl and the dye of the formula (1), in which R, is methyl and R2 is isopropyl is likewise particularly preferred.
The present invention furthermore relates to a process for the preparation of the dye mixtures of the formula (1). The mixtures according to the invention can be prepared, for example, by mixing at least two structurally different individual dyes of the general formula (1), which are known per se, with one another in the desired ratio, or by diazotizing a diazo component of the formula N02 R10--. - NH2 (8), 26 CH3 CH2CH(CH3)2 C6H5 CH2CH3 27 CH3 C(CH3)3 C6H5 CH2CH3 28 CH3 CH(CH3)2 C^ CH2CH3 in which R, is as defined under formula (1), and coupling the product to a mixture of at least two coupling components of the formula CH 3 C1M 0 N HO R2 (9), which differ from one another in the substituent R2 and in which R2 is as defined under formula (1).
The dye mixtures of the formula (1) according to the invention can be used as dyes for dyeing and printing semi-synthetic and, in particular, synthetic hydrophobic fibre materials, in particular textile materials. Textile materials of blend fabrics which comprise such semisynthetic or synthetic hydrophobic textile materials can likewise be dyed or printed with the aid of the dye mixtures according to the invention.
Semi-synthetic textile materials are, in particular, cellulose 2112acetate and cellulose triacetate.
Synthetic hydrophobic textile materials comprise, in particular, linear, aromatic polyesters, for example those of terephthalic acid and glycols, in particular ethylene glycol, or condensation products of terephthalic acid and 1,4-bis-(hydroxymethyl)-cyclohexane; polycarbonates, for example those of (x,(x-dimethyi-4,4'-dihydroxy-diphenyi-methane and phosgene, and fibres based on polyvinyl chloride and polyamide.
The dye mixtures according to the invention are applied to the textile materials by known dyeing processes. For example, polyester fibre materials are dyed by the exhaust method from an aqueous dispersion in the presence of customary anionic or nonionic dispersants and, if appropriate, customary swelling agents (carders) at temperatures between 80 and 1400C. Cellulose-2112-acetate is preferably dyed at between approximately 65 and 850C, and cellulose triacetate is dyed at temperatures up to 11 50C.
The dye mixtures according to the invention do not stain or only slightly stain wool and cotton simultaneously present in the dyebath (very good reserve), so that they can also be used in particular for dyeing polyesterlwool and polyester/cellulose fibre blend fabrics.
The dye mixtures according to the invention are suitable for dyeing by the thermosol method, in the exhaust method and for printing processes. The exhaust method is preferred. The liquor ratio depends on the apparatus circumstances, on the substrate and on the make-up. However, it can be chosen within a wide range, for example 1:4 to 1: 100, but is preferably between 1:6 and 1:25.
The textile material mentioned can be present here in various forms of processing, for example as fibre, thread or non-woven and as a woven fabric or knitted fabric.
It is advantageous to convert the dye mixtures according to the invention into a dye preparation before their use. For this, the dye mixture is ground so that its particle size is on average between 0.1 and 10 microns. Grinding can be carried out in the presence of dispersants. For example, the dried dye mixture is ground with a dispersant or kneaded in paste form with a dispersant and then dfled in vacuo or by spraying. Printing pastes and dyebaths can be prepared with the preparations thus obtained, after addition of water.
In the case of printing, the customary thickeners, for example modified or non-modified natural products, for example alginates, British gum, gum arabic, crystal gum, carob bean flour, tragacanth, carboxymethylcellulose, hydroxyethylcellulose, starch or synthetic products, for example polyacryla m ides, polyacrylic acid or copolymers thereof, or polyvinyl alcohols, are used.
The dye mixtures according to the invention impart to the materials mentioned, in particular polyester material, level yellow or golden yellow colour shades of very good in-use fastness properties, such as, in particular, good fastness to light and good fastness to sublimation. The very good fastness to washing is to be emphasized. The dyes according to the invention are furthermore distinguished by a good exhaustion and build-up.
The dye mixtures according to the invention can also be used in particular for the preparation of mixed shades together with other dyes or together with a suitable red and blue dye for trichromatic dyeing.
The present invention also relates to the abovementioned uses of the dye mixtures of the formula (1) according to the invention, as well as a process for dyeing or printing semisynthetic or synthetic hydrophobic fibre material, in particular textile material, which comprises applying the dye mixture of the formula (1) according to the invention to the material mentioned or incorporating it into this. The hydrophobic fibre material mentioned is preferably textile polyester material. Other substrates which can be treated by the process according to the invention and preferred process conditions are to be found above in the more detailed explanation of the use of the dye mixtures according to the invention.
The invention also relates to the hydrophobic fibre material, preferably polyester textile material, dyed or printed by the process mentioned.
The following examples serve to illustrate the invention. In these, unless stated otherwise, parts are parts by weight and percentages are percentages by weight. The temperatures are stated in degrees Celsius. Parts by weight bear the same relation to parts by volume as the gram to the cubic centimetre.
Example 1
A suspension of 33.6 parts of 2-nitro-4-methoxyaniline in 220 parts of water is cooled to about 10 - 150C, and 60 parts of 32% hydrochloric acid are added dropwise. 55 parts of a 4N sodium nitrite solution are then added in the course of 15 minutes, with thorough stirring, the temperature of the reaction mixture being kept at about 150C. When the addition has ended, the mixture is subsequently stirred for a further hour and the excess nitrite is destroyed with a little amidosulphonic acid. The resulting diazotization mixture is allowed to run slowly into a solution, cooled to about 5 - 1 OOC, of 20.4 parts of N-isopropyl-3-cyano4-methyi-5hydroxypyridone, 21.8 parts of N-buty]-3-cyano-4-methyl-5hydroxypyridone and 18 parts of a 30% aqueous sodium hydroxide solution in 200 parts of water. During the addition of the diazotization mixture, the pH is kept constant at between 5 and 6 with a 30% aqueous sodium hydroxide solution. The orange-red suspension is subsequently stirred at 15 - 200C for about a further hour. The precipitate is filtered off with suction, rinsed with water and dried at 7M in vacuo. 75.5 parts of dye mixture No. 1 are obtained. The dye mixture dyes polyester in brilliant golden yellow shades with good fastness properties, in particular with very good fastnesses to washing.
Example 2
A suspension of 11.5 parts of 2-nitro-4-phenoxyani line in 100 parts of water and 20 parts of 32% hydrochloric acid is stirred at 40 - 500C for 30 minutes. The mixture is then cooled to 15 - 2WC, and 15 parts of a 4N sodium nitrite solution are added, with thorough stirring. When the addition has ended, the reaction mixture is subsequently stirred at about 20C for a further two hours. The excess nitrite is destroyed with amidosulphonic acid and the diazotization mixture is clarified by filtration. The clear diazonium salt solution thus prepared is allowed to run slowly into a solution, cooled to about 10 - WC, of 5.2 parts of Wethyl-3- cyano-4-methyi-5-hydroxypyridone, 6.1 parts of N-isopropoxypropyi-3-cyano- 4-methyi-5hydroxypyridone and 4.2 parts of a 30% aqueous sodium hydroxide solution in 100 parts of water. During the addition of the diazonium salt solution, the pH is kept constant at between 5 and 6 with a 30% aqueous sodium hydroxide solution. The orange-red suspension is subsequently stirred at 15 - 200C for about a further hour. Thereafter, the precipitate is filtered off with suction, rinsed with water and dried at 700C in vactio. 22 parts of dye mixture No. 14 are obtained. The dye mixture dyes polyester in brilliant golden yellow shades with good fastness properties, in particular with very good fastnesses to washing.
Example 3
The dye mixtures 2 - 13 and 15 - 28 listed with priority in Table 1, which likewise dye polyester in brilliant golden yellow shades with good fastness properties, in particular very good fastnesses to washing, are obtained analogously to the processes described in Examples 1 and 2 or by mixing two structurally different dyes of the formula (1).
Example 4 g of polyester fabric are immersed at a liquor ratio of 1:20 in a liquor comprising 1 g of dye mixture No. 5, 1 gli of ammonium sulphate and 0.5gi of a commercially available levelling agent, which has been adjusted to pH 4.5 - 5 with 80% formic acid, at room temperature. The liquor is then heated up, first to 600C at a heating-up rate of 30CIminute and then to 1300C with a heating-up rate of 20C/minute. Dyeing is carried out at 1300C for 60 minutes. The liquor is then cooled to 400C and the dyed polyester fabric is washed with water and cleaned reductively in a bath comprising 5 mill of 30% sodium hydroxide solution, 2 g/1 of 85% sodium dithionite solution and 1 glI of a commercially available detergent at 70 - 80C for 20 minutes. The finished dyeing is then washed with water and dried. A brilliant golden yellow dyeing with excellent fastnesses to washing is obtained.
Claims (17)
1. A dye mixture comprising at least two structurally different dyes, each of which has the formula N02 H3C CN R1 O-C N = N N 0 HO R2 (1) in which R, is Cl-C4alkyl and R2 is isopropy], n-butyl, isobutyl, sec- butyl or tert-butyl; or Cl-C3alkyl which is substituted by phenyl or phenoxy; or R, is phenyl which is unsubstituted or substituted by Cl- C4alkyl, Cl-C4alkoxy, hydroxyl or halogen; Cl-C4alkoxy-Cl-C3alkylene, phenoxy-Cl-C3alkylene or Cl-C3alkyl which is substituted by phenyl which is unsubstituted or substituted by Cl-C4alky], Cl-C4alkoxy, hydroxyl or halogen and R2 is Cl-Cloalkyl which is unsubstituted or substituted by hydroxyl, 0COR3 or phenoxy, where the phenyl ring in phenoxy is unsubstituted or substituted by Cl-COlkyl, Cl-COlkoxy, hydroxyl or halogen and the alkyl chain in Cl-Cloalkyl from C3 can be interrupted by one or more oxygen atoms; phenyl which is unsubstituted or substituted by Cl-COlkyl, Cl-COlkoxy, hydroxyl or halogen; or CS-C7CYCloalky]; and R3 is Cl-COlkyl.
2. A dye mixture according to claim 1 comprising at least two dyes of the formula (1) which contain the same substituent R2 and different substituents R,.
3. A dye mixture according to claim 1 comprising at least two dyes of the formula (1) which contain the same substituent R, and different substituents R2.
4. A dye mixture according to claim 1 comprising at least two dyes of the formula (1) which contain different substituents R, and R2.
5. A dye mixture according to claim 3, in which R, is methyl.
6. A dye mixture according to claim 3, in which R, is phenyl which is unsubstituted or substituted by Cl-C4alkyl, Cl-C4alkoxy, hydroxyl or halogen.
7. A dye mixture according to claim 6 in which R, is phenyl.
8. A dye mixture according to claim 3, comprising two dyes of the formula (1) in which both dyes contain methyl as R, and, differently to one another, isopropyl, n-butyi, isobutyl, secbutyl or tert-butyl as R2.
9. A dye mixture according to claim 3, comprising two dyes of the formula (1) in which the two dyes contain phenyl as R.i, and, differently to one another, methyl, ethyl, methoxyethy], methoxypropyl, ethoxypropyl or isopropoxypropyl as R2.
10. A dye mixture according to claim 4, comprising two dyes of the formula (1) in which one dye contains methyl as R, and isopropyl, n-buty], isobutyl, sec-butyl or tert-butyl as R2 and the other dye contains phenyl as R, and methyl or ethyl as R2.
11. A process for the preparation of a dye mixture according to claim 1, which comprises diazotizing a diazo component of the formula N02 RIO--. NH2 (8), in which R, is as defined under formula (1), and coupling the product to a mixture of at least two coupling components of the formula CH3 CIN 0 N HO R (9), which differ from one another in the substituent R2 and in which R2 is as defined under formula (1).
12. The use of a dye mixture of the formula (1) according to claim 1 for dyeing or printing semi-synthetic or synthetic hydrophobic fibre material, in particular textile material.
13. A process for dyeing or printing semi-synthetic or synthetic hydrophobic fibre material, in particular textile material, which comprises applying the dye mixture of the formula (1) according to claim 1 to the material mentioned or incorporating it into this.
14. A process according to claim 13 in which the hydrophobic fibre material is textile material.
15. A process according to claim 14 in which the textile material is polyester textile material.
16. The hydrophobic fibre material dyed or printed according to any of claims 13 to 15.
17. A dye mixture according to claim 1 substantially as hereInbefore described with reference to any one of the foregoing Examples.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH330495A CH689980A5 (en) | 1995-11-22 | 1995-11-22 | Mixtures of monoazopyridone dyes. |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| GB9623772D0 GB9623772D0 (en) | 1997-01-08 |
| GB2307479A true GB2307479A (en) | 1997-05-28 |
| GB2307479B GB2307479B (en) | 1999-12-01 |
Family
ID=4253097
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB9623772A Expired - Fee Related GB2307479B (en) | 1995-11-22 | 1996-11-15 | Mixtures of monoazopyridone dyes |
Country Status (3)
| Country | Link |
|---|---|
| CH (1) | CH689980A5 (en) |
| DE (1) | DE19646429A1 (en) |
| GB (1) | GB2307479B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2016513140A (en) * | 2013-01-14 | 2016-05-12 | ダイスター・カラーズ・ディストリビューション・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | Highly wet fast disperse dye mixture |
| CN108102422A (en) * | 2017-12-12 | 2018-06-01 | 浙江龙盛化工研究有限公司 | A kind of yellow disperse dye composition and dye preparations |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2754698A1 (en) | 2013-01-14 | 2014-07-16 | DyStar Colours Distribution GmbH | High wet-fast disperse dye mixtures |
| EP2754697A1 (en) | 2013-01-14 | 2014-07-16 | DyStar Colours Distribution GmbH | High wet-fast disperse dye mixtures |
| EP2754748A1 (en) * | 2013-01-14 | 2014-07-16 | DyStar Colours Distribution GmbH | High wet fast disperse dye mixtures |
| EP3715423B1 (en) | 2019-03-27 | 2022-05-11 | DyStar Colours Distribution GmbH | High wet fast disperse dye mixtures of n-[4-(5-fluoro-2,4-dinitro-phenylazo)-phenyl]-amine derivatives and n-[4-(4-nitro-phenylazo)-phenyl]-amine derivatives |
| EP3715424A1 (en) | 2019-03-27 | 2020-09-30 | DyStar Colours Distribution GmbH | High wet fast disperse dye mixtures of n-[4-(5-thiocyanato-2,4-dinitro-phenylazo)-phenyl]-amine derivatives and n-[4-(4-nitro-phenylazo)-phenyl]-amine derivatives |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0378167A1 (en) * | 1989-01-10 | 1990-07-18 | Sumitomo Chemical Company, Limited | Disperse dye composition useful for dyeing or printing hydrophobic fiber materials |
| EP0385330A2 (en) * | 1989-03-02 | 1990-09-05 | BASF Aktiengesellschaft | Mixtures of dyestuffs comprising azo compounds on the basis of phenylox diazolyl aniline |
-
1995
- 1995-11-22 CH CH330495A patent/CH689980A5/en not_active IP Right Cessation
-
1996
- 1996-11-11 DE DE1996146429 patent/DE19646429A1/en not_active Withdrawn
- 1996-11-15 GB GB9623772A patent/GB2307479B/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0378167A1 (en) * | 1989-01-10 | 1990-07-18 | Sumitomo Chemical Company, Limited | Disperse dye composition useful for dyeing or printing hydrophobic fiber materials |
| EP0385330A2 (en) * | 1989-03-02 | 1990-09-05 | BASF Aktiengesellschaft | Mixtures of dyestuffs comprising azo compounds on the basis of phenylox diazolyl aniline |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2016513140A (en) * | 2013-01-14 | 2016-05-12 | ダイスター・カラーズ・ディストリビューション・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | Highly wet fast disperse dye mixture |
| US9534118B2 (en) | 2013-01-14 | 2017-01-03 | Dystar Colours Distribution Gmbh | High wet fast disperse dye mixtures |
| JP2018076511A (en) * | 2013-01-14 | 2018-05-17 | ダイスター・カラーズ・ディストリビューション・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | High wet fast disperse dye mixtures |
| JP2018083947A (en) * | 2013-01-14 | 2018-05-31 | ダイスター・カラーズ・ディストリビューション・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | High wet fast disperse dye mixtures |
| CN108102422A (en) * | 2017-12-12 | 2018-06-01 | 浙江龙盛化工研究有限公司 | A kind of yellow disperse dye composition and dye preparations |
| CN108102422B (en) * | 2017-12-12 | 2019-08-13 | 浙江龙盛化工研究有限公司 | A kind of yellow disperse dye composition and dye preparations |
Also Published As
| Publication number | Publication date |
|---|---|
| CH689980A5 (en) | 2000-02-29 |
| DE19646429A1 (en) | 1997-05-28 |
| GB9623772D0 (en) | 1997-01-08 |
| GB2307479B (en) | 1999-12-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 730 | Substitution of applicants allowed (sect. 30/1977) | ||
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 20081115 |