GB2307480A - 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
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- GB2307480A GB2307480A GB9623773A GB9623773A GB2307480A GB 2307480 A GB2307480 A GB 2307480A GB 9623773 A GB9623773 A GB 9623773A GB 9623773 A GB9623773 A GB 9623773A GB 2307480 A GB2307480 A GB 2307480A
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- 239000000203 mixture Substances 0.000 title claims description 48
- -1 5-(4'-substituted-3'-nitrophenylazo)-N-substituted-3-cyano-4-methyl-6-hydroxypyrid-2-ones Chemical class 0.000 title description 4
- 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 68
- 239000000463 material Substances 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 238000004043 dyeing Methods 0.000 claims description 14
- 239000004753 textile Substances 0.000 claims description 14
- 239000000835 fiber Substances 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 229920000728 polyester Polymers 0.000 claims description 11
- 230000002209 hydrophobic effect Effects 0.000 claims description 10
- 238000002360 preparation method Methods 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
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 2
- 150000001989 diazonium salts Chemical class 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000005406 washing Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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 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
- QHMGJGNTMQDRQA-UHFFFAOYSA-N dotriacontane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC QHMGJGNTMQDRQA-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- HOWGUJZVBDQJKV-UHFFFAOYSA-N docosane Chemical compound CCCCCCCCCCCCCCCCCCCCCC HOWGUJZVBDQJKV-UHFFFAOYSA-N 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical group CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- 229920002284 Cellulose triacetate Chemical group 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 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 group 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
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000010438 heat treatment Methods 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
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 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
- 239000000725 suspension Substances 0.000 description 2
- 229920002994 synthetic fiber Polymers 0.000 description 2
- WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-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
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 240000008886 Ceratonia siliqua Species 0.000 description 1
- 235000013912 Ceratonia siliqua Nutrition 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-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
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 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
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 235000010443 alginic acid Nutrition 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
- 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
- 125000001246 bromo group Chemical group Br* 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
- 239000000969 carrier Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 125000001153 fluoro group Chemical group F* 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
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 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
- 229930014626 natural product Natural products 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920002401 polyacrylamide Polymers 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
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 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
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000000967 suction filtration Methods 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
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)
- Pyridine Compounds (AREA)
Description
1-20650/A Mixtures of monoazopyridone dyes 2307480 The present invention
relates to mixtures of monoazopyridone dyes, to their preparation and to the use thereof for dyeing or printing textile fibre materials.
Monoazopyridone dyes and the use thereof for dyeing synthetic fibre materials are known, inter alia, from EP-A-0 440 072. It has been found, however, that these dyes do not always completely meet the highest demands. Accordingly, there is a need for novel dyes or dye combinations which have, in particular, better exhaust or build-up properties or better fastness to washing.
Surprisingly, is has now been found that the mixtures of this invention exhaust to a high degree to the fibre, have an excellent build-up and that the resulting dyeings have good fastness to light, sublimation and washing.
Accordingly, the invention relates to a dye mixture comprising at least two structurally different dyes, each corresponding to the formula NO 2 H3C CN Rio--o N = N 0 N X HO R2 (1), wherein R, is Cl-C4alkyl, R2 is the (CH2),0-Rs radical, R5 is, independently of IR,, Cl-C4alkyl, phenyl which is unsubstituted or substituted by Cl- C4alkyl, Cl-C4alkoxy, hydroxy or halogen, and n is 2 or 3.
Cl-C4alkyl in formula (1) is methyl, ethyl, isopropyl, n-propyi, isobutyl, n-butyl, sec-butyl or tert-buty]. Cl-C4alkoxy in formula (1) is methoxy, ethoxy, isopropoxy, propoxy, n-butoxy, isobutoxy, sec-butoxy or tertbutoxy.
Halogen in formula (1) is typically fluoro, bromo or, preferably, chloro.
The structurally different dyes of formula (1) in the dye mixtures of this invention can comprise identical substituents R, and different substituents R2, or identical substituents R2 and different substituents R,, or different substituents R, and R2.
Preferred dye mixtures are those comprising two structurally different dyes of formula (1). The ratio of the individual dyes of the dye mixtures of this invention can vary within a wide range, for example from 1:1 up to 1:5. Preferred dye mixtures are those wherein the two dyes are in a ratio from 1:1 to 1:3. Particularly preferred dye mixtures are those wherein the dyes are in a ratio 1A.
Preferred dye mixtures are those which comprise dyes of formula (1), wherein R, is methyl.
Particularly preferred are the following dye mixtures of the structurally different dyes (A) and (B) of formula (1) listed in Table 1:
Table 1
Dye (A) Dye (B) Dye mixture No. R, R2 R, R2 1 CH3 (CH2)30CH3 CH3 (CH2)30C2Hs 2 CH3 (CH2)30CH3 CH3 (CH2)30CH(C1-13)2 3 CH3 (CH2)30C2H5 CH3 (CH2)30CH(CH3)2 4 CH3 (CH2)30CH3 CH3 (CH2)30C6Hs CH3 (CH2)30C2H5 CH3 (CH2)30C6Hs 6 CH3 (CH2)30CH(CH3)2 CH3 (CH2)30C6H5 7 CH3 (CH2)30CH3 CH3 (CH2)20CH3 8 CH3 (C1-12)30CH(CH3)2 CH3 (CH2)20CH3 9 CH3 (CH2)30C21-15 CH3 (CH2)20CH3 CH3 (CH2)20C61-15 CH3 (CH2)20CH3 11 C2H5 (CH2)30CH3 CH3 (CH2)30CH3 12 n-C4H9 (CH2)30CH3 CH3 (CH2)30CH3 13 C2H5 (CH2)30CH(C1-13)2 CH3 (CH2)30CH3 The invention also relates to a process for the preparation of the dye mixtures of formula (1). The mixtures of this invention can be prepared, for example, by mixing at least two structurally different single dyes of the general formula (1), which are known per se, in the desired ratio, or by diazotising a diazo component of formula N02 R10--NH2 (2), wherein R, has the meaning given for formula (1), and coupling the diazonium compound so obtained to a mixture of at least two coupling components of formula CH3 CN 0 rN HO R2 (3).
14 C21-1s (CH2)30CH3 CH3 (CH2)30CH(CH3)2 C21-1s (CH2)30CH3 C2H5 (CH2)30CH( which differ from each other in the substituent R2 and wherein R2 has the meaning given for formula (1).
The dye mixtures of this invention of formula (1) can be used for dyeing and printing semisynthetic and, in particular, synthetic hydrophobic fibre materials, preferably textile materials. Textile materials of blends comprising such semi-synthetic or synthetic hydrophobic textile materials can also be dyed or printed with the dye mixtures of this invention.
Suitable semi-synthetic textile materials are, in particular, cellulose secondary acetate and cellulose triacetate.
Synthetic hydrophobic textile materials consist mainly of linear aromatic polyesters, typically of terephthalic acid and glycols, in particular ethylene glycol, or condensates of terephthalic acid and 1,4bis(hydroxymethyi)cyclohexane; of polycarbonates, typically of cL,adimethyi4,4'-dihydroxydiphenyimethane and phosgene, of fibres based on polyinyl chloride and polyamide.
The dye mixtures of this invention are applied to the textile materials by known dyeing processes. Typically, polyester fibre materials are dyed by the exhaust process from an aqueous dispersion in the presence of customary anionic or nonionic dispersants and, if appropriate, customary swelling agents (carriers), in the temperature range from 80 to 1400C. Cellulose secondary acetate is preferably dyed at a temperature from about 65 to WC, and cellulose triacetate at a temperature of up to 1150 C.
The dye mixtures of this invention do not, or only slightly, stain wool and cotton simultaneously present in the dye bath (very good reserve) and are accordingly also well suited for dyeing blends of polyesterlwool and of polyester/celluiose fibre.
The dye mixtures of this invention are suitable for dyeing by the thermosol process, the exhaust process and the printing process. The exhaust process is preferred. The liquor ratio depends on the apparatus employed, on the substrate and on the form of presentation, but can be chosen from a wide range, for example from 1:4 to 1:100. The preferred liquor ratio, however, is from 1:6 to 1:25.
Said textile material may be in different forms of presentation, for example fibres, filaments or nonwoven fabrics, woven or knitted fabrics.
It is useful to convert the dye mixtures of this invention prior to their use into a dye preparation. To this purpose the dye mixture is ground to an average particle size of 0. 1 to 10 micron. Grinding can be carried out in the presence of dispersants. Typically, the dried dye mixture is ground with a dispersant or kneaded as a paste together with a dispersant and then vacuum dried or by spray dried. Printing pastes and dye baths can be prepared with the preparations so obtained after the addition of water.
The conventional thickeners are used for printing, typically modified or non-modified natural products, such as alginates, British gum, gum arabic, crystal gum, carob bean flour, tragacanth, carboxymethylcellulose, hydroxyethylcellulose, starch or synthetic products, e.g. polyacrylamides, polyacrylic acid or the copolymers thereof, or polyvinyl alcohols.
The dye mixtures of this invention impart to the cited materials, in particular to polyester material, level yellow or golden yellow shades, very good end-use fastness properties, such as, in particular, good fastness to light and sublimation. The excellent fastness to washing merits special mention. The dyes of this invention are also distinguished by good exhaustion and build-up.
The dye mixtures of this invention are also well suited for producing combination shades with other dyes or with a suitable red and blue dye for trichromatic dyeing.
The invention also relates to the above uses of the dye mixtures of this invention as well as to a process for dyeing or printing semi-synthetic or synthetic hydrophobic fibre material, in particular textile material, which process comprises applying the dye mixture of this invention to said material or incorporating it therein. This hydrophobic fibre material is preferably textile polyester material. Other substrates which may be treated by the novel process, as well as preferred process conditions, can be found in the detailed description of the use of the dye mixtures of this invention.
In another of its aspects, the invention relates to the hydrophobic fibre material, preferably polyester textile material, dyed or printed by said process.
The following Examples illustrate the invention in more detail. Parts are parts by weight and the percentages are by weight, unless otherwise stated. The temperatures are given in degrees Celsius. The relationship between parts by weight and parts by volume is the same as that between the gram and 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 - 15' C and then 60 parts of 32 % hydrochloric acid are added dropwise. Over 15 minutes, 55 parts of a 4N sodium nitrite solution are added, with thourough stirring, the temperature of the reaction mixture being kept at about 150 C. After the addition is complete, stirring is continued for another hour and excess nitrite is destroyed with a small amount of amidosuifonic acid. The resuffing diazotisation mixture is slowly run into a solution, which is cooled to about 5 - 1 W' C, of 23.5 parts of N-methoxylpropyl-3-cyano4methyl-5-hydroxypyddone, 26.5 parts of N-isopro-poxypropyl-3-cyano-4methyi-5-hydroxypyridone and 19 parts of a 30% aqueous solution of sodium hydroxide in 200 parts of water. During the addition of the diazotisation mixture, the pH is kept constant at a value from 5 to 6 with a 30 % aqueous solution of sodium hydroxide. The orange-red suspension is stirred for about 1 hour at 15 - 200 C. The precipitate is collected by suction filtration, washed with water and dried at 700 C under vacuum, giving 75.5 parts of the dye mixture No. 2. The dye mixture dyes polyester in a brilliant golden yellow shade having good fastness properties, in particular excellent fastness to washing.
Example 2
In general accordance with the process described in Example 1 or by mixing two structurally different dyes of formula (1), the dye mixtures 1 and 3 to 15 listed in Table 1 as priority are obtained which also dye polyester in a brilliant golden yellow shade having good fastness properties, in particular excellent fastness to washing.
Example 3 g of polyester fabric are immersed at room temperature and at a liquor ratio of 1:20 in a liquor comprising 1 g of the dye mixture No. 2, 1 g/] of ammonium sulfate, and 0.5 g/1 of a commercial levelling agent, the pH being adjusted to 4.5 - 5 with 80% formic acid. The liquor is then heated first at a heating rate of 3 C/min to 600 C and then at a heating rate of 20 C to 1300 C. Dyeing is carried out for 60 minutes at 130 C. The liquor is then cooled to 400 C, the dyed polyester fabric is washed with water and cleaned reductively in a bath containing 5 mill of a 30% solution of sodium hydroxide, 2 g/1 of a 85% solution of sodium dithionite and 1 g/1 of a commercial detergent for 20 minutes at 70 - 80' C. The ready dyeing is then washed with water and dried. A brilliant golden yellow dyeing is obtained having excellent fastness to washing.
Claims (13)
1. A dye mixture, comprising at least two structurally different dyes, each corresponding to formula N02 H3C CN RIO-d N=N_ \ N 0 HO R2 (1), wherein R, is Cl-C4alkyl, R2 is the (C1-12)nO-R5 radical, Rs is, independently of IR,, Cl-C4alkyl, phenyl which is unsubstituted or substituted by Cl-CAlkyl, Cl-C4alkoxy, hydroxy or halogen, and n is 2 or 3.
2. A dye mixture according to claim 1, comprising at least two dyes of formula (1), which comprise identical substituents R2 and different substituents IR,.
3. A dye mixture according to claim 1, comprising at least two dyes of formula (1), which comprise identical substituents R, and different substituents R2.
4. A dye mixture according to claim 1, comprising at least two dyes of formula (1), which comprise different substituents R, and R2.
5. A dye mixture according to claim 1 or 3, wherein R, is methyl.
6. A dye mixture according to claim 3, comprising two dyes of formula (1), in which two dyes R, is methyl and Rs, differing from each other, is methyl, ethyl, isopropyl or phenyl.
7. A process for the preparation of the dye mixture according to claim 1, which process comprises diazotising a diazo component of formula N02 R10--- - NH2 (2), wherein R, has the meaning given for formula (1), and coupling the diazonium compound so obtained to a mixture of at least two coupling components of formula CH3 CN 0 N HO R2 (3), which differ from each other in the substituent R2 and wherein R2 has the meaning given for formula (1).
8. Use of the dye mixture of formula (1) according to claim 1 for dyeing or printing semisynthetic or synthetic hydrophobic fibre material, in particular textile material.
9. A process for dyeing or printing semi-synthetic or synthetic hydrophobic fibre material which process comprises applying the dye mixture of formula (1) according to claim 1 to said material or Incorporating it therein.
W
10. A process according to claim 9 in which the hydrophobic fibre material is textile material.
11. A process according to claim 10 In which the textile material is polyester textile material.
12. The hydrophobic fibre material which Is dyed or printed according to any of claims 9 to 11.
13. A dye mixture according to claim 1 substantially as herelnbefore described with reference to any one of the foregoing Examples.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH330795A CH689832A5 (en) | 1995-11-22 | 1995-11-22 | Mixtures of Monoazopyridonfarbstoffen. |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| GB9623773D0 GB9623773D0 (en) | 1997-01-08 |
| GB2307480A true GB2307480A (en) | 1997-05-28 |
| GB2307480B GB2307480B (en) | 1999-08-25 |
Family
ID=4253161
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB9623773A Expired - Fee Related GB2307480B (en) | 1995-11-22 | 1996-11-15 | Mixtures of monoazopyridone dyes |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPH09176508A (en) |
| CH (1) | CH689832A5 (en) |
| DE (1) | DE19646430A1 (en) |
| GB (1) | GB2307480B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102008054531A1 (en) * | 2008-12-11 | 2010-06-17 | Dystar Textilfarben Gmbh & Co. Deutschland Kg | Mixtures of disperse dyes |
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 CH330795A patent/CH689832A5/en not_active IP Right Cessation
-
1996
- 1996-11-11 DE DE1996146430 patent/DE19646430A1/en not_active Withdrawn
- 1996-11-15 GB GB9623773A patent/GB2307480B/en not_active Expired - Fee Related
- 1996-11-20 JP JP8309454A patent/JPH09176508A/en active Pending
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 |
Also Published As
| Publication number | Publication date |
|---|---|
| GB9623773D0 (en) | 1997-01-08 |
| JPH09176508A (en) | 1997-07-08 |
| DE19646430A1 (en) | 1997-05-28 |
| GB2307480B (en) | 1999-08-25 |
| CH689832A5 (en) | 1999-12-15 |
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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: 20061115 |