GB2300863A - Monoazo disperse dyestuffs - Google Patents
Monoazo disperse dyestuffs Download PDFInfo
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- GB2300863A GB2300863A GB9609994A GB9609994A GB2300863A GB 2300863 A GB2300863 A GB 2300863A GB 9609994 A GB9609994 A GB 9609994A GB 9609994 A GB9609994 A GB 9609994A GB 2300863 A GB2300863 A GB 2300863A
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- Prior art keywords
- formula
- alkyl
- dyestuff
- signifies
- monoazo disperse
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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
- 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
-
- 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
- C09B43/00—Preparation of azo dyes from other azo compounds
- C09B43/30—Preparation of azo dyes from other azo compounds by esterification of —COOH or —SO3H groups
-
- 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
- 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
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/008—Preparations of disperse dyes or solvent dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Coloring (AREA)
- Thermal Transfer Or Thermal Recording In General (AREA)
- Pyridine Compounds (AREA)
- Paints Or Removers (AREA)
- Polymerisation Methods In General (AREA)
Abstract
The monoazo disperse dyestuff of formula I wherein R signifies phenyl, optionally substituted, or a group of formula R'-O-; ' signifies C 3-4 -alkenyl, C 3-4 -alkynyl, phenyl, or C 1-8 -alkyl (where the C 1-8 -alkyl bears one or two substituents, and the C 3-4 -alkenyl and phenyl groups are optionally substituted); 1 signifies hydrogen or C 1-2 alkyl; 2 signifies hydrogen or halogen; 3 signifies hydrogen or C 1-3 -alkyl; and 4 signifies hydrogen, linear or branched C 1-8 -alkyl which optionally bears one substituent), or an amino group (which optionally bears one substitutent); the dyestuff being free from water-solubilizing groups] and the mixtures thereof, are suitable for dyeing or printing fibres or threads or materials produced therefrom, the fibres, threads or materials comprising either fully or semi-synthetic, hydrophobic, organic substances.
Description
MONOAZO DISPERSE DYESTUFFS
It has been found that the monoazo disperse dyestuffs of formula I
wherein R signifies phenyl, optionally substituted, or a group of formula R'-O
R' signifies C3-4-alkenyl, C3-4-alkynyl, phenyl, or C1-8-alkyl which bears
one or two substituents,
R1 signifies hydrogen or C, 2-alkyl, R2 signifies hydrogen or halogen,
R3 signifies hydrogen or C, 3-alkyl, and
R4 signifies hydrogen, linear or branched C, 8-alkyl which optionally
bears one substituent, or an amino group which optionally bears one
substituent, the dyestuff being free from water-solubilizing groups, and mixtures of said dyestuffs, are eminently suitable for dyeing or printing fibres or threads or materials produced therefrom, the fibres, threads or materials, comprising either fully or semi-synthetic, hydrophobic, organic substances.
When R is phenyl it may be substituted by for example chlorine, -OCH3, -CH3 or NO2.
A suitable substituted amino group is for example -NHC6H5
In formula I, preferably
R signifies unsubstituted phenyl or the group R'-O-, signifies C1-@ -alkyl, preferably C1-4-alkykl which bears a substituent
from the series halogen and C1-4-alkoxy; phenyl; phenyl-C1.3-alkyl or
phenoxy-C1-2-alkyl, whereby the phenyl nuclci may bear a substituent
from the series chlorine, bromine, nitro, C1-2-alkyl or C, 2-alkoxy; tetrahydrofurfuryl;C3-4-alkenyl, C3-4-alkynyl or 1-phenyl-propenyl,
R, and R2 signify hydrogen,
R3 signifies methyl, and
R4 signifies hydrogen, C,4-alkyl or C1-4-alkoxy-C2-3-alkyl
Particularly preferred are dyestuffs of formula I and mixtures thereof, wherein:
R is phenyl or
R' is benzyl, phenoxyethyl or the radical Cl-(CH2)4- and;
R, and R2 are hydrogen,
R3 is methyl. and R, is C,4-alkyl or C1 ,-alkoxypropyl.
Dyestuffs of formula I and mixtures thereof, wherein R, signifies a linear or branched C1alkyl radical are most preferred. Preferably the alkyl radical is unsubstituted. When substituents are present they are preferably selected from the group of C6H5-, Cl or -OCOCH3.
Production of these dyestuffs is effected either by coupling a diazotised amine of formula II
with an amine of formula
or by the condensation of a compound of formula IV
with a compound of formula V
Diazotization and coupling are effected by generally known processes.
By halogen is meant fluorine, chlorine, bromine or iodine, preferably chlorine or bromine, especially chlorine.
The condensation of the compounds of formula IV with those of formula V is similarly effected in a manner familiar to the person skilled in the art, preferably in an organic solvent and in the presence of a basic compound which binds the hydrogen halide that is formed.
The compounds of formulae II to V are known or may be easily produced in a manner familiar to the person skilled in the art
The processing of the new compounds of formula I, obtainable according to either of the above processes, into dyeing preparations is effected in a generally known manner, e.g. by grinding in the presence of dispersing agents andlor fillers. Dyeing, paddyeing or printing may take place in for example a so-called long or short bath, after the addition of water, using the preparations which have optionally been dried according to conventional methods for example by drying in a vacuum, by spray drying or by using a fluidised bed granulator.
The dyestuffs of the present invention or mixtures thereof demonstrate excellent dyeings when an aqueous suspension of the dyestuff or mixture thereof is used to treat textile material comprising fully synthetic or semi-synthetic, hydrophobic, high molecular weight organic materials. They are especially suitable for dyeing or printing textile material consisting of linear, aromatic polyesters, as well as cellulose-2-acetate and cellulose triacetate.
Dyeing or printing is effected in accordance with known processes, e.g. those described in
French patent application no. 1.445.371.
The dyeings or printings thus obtained, have good all-round fastness; particularly noticeable are the thermo-migration fastness, light fastness, thermofixation-, sublimationand pleating fastness, as well as the excellent wet fastness (especially as measured by the
M & C4A washing test), especially following thermal treatment.
The new dyestuffs or mixtures thereof are also particularly suitable for the modern rapid dyeing processes e.g the ForonR Rapid Dyeing process.
The new dyestuffs or mixtures thereof are similarly suitable for modern imaging processes, e.g. "thermo-transfer printing".
In the following examples, the parts and percentages are by weight. The temperatures are given in degrees celsius.
EXAMPLE 1 28.1 parts of 4-amino-benzoic acid-(l-carbobenzyloxySmethyl-ester are stirred into 30 parts of water and 30 parts of 30% hydrochloric acid over 2 hours, and after adding 30 parts of ice, 22 parts of a 4N sodium nitrite solution are added at 5-10". After adding a further 30 pans of ice and stirring for 30 minutes, the slight excess of nitrous acid is broken down with amidosulphonic acid, and the resultant diazonium salt solution is filtered.The cold, clear-filtered diazonium salt solution is slowly dispensed into a solution of 21 pans of N-butyl-3-cyanoXmethyl-pyridone-2 in 110 parts of water, which has been set at pH 7 - 7.5 and has been mixed with a few seed crystals of the dyestuff of formula I, whereby during coupling the temperature range of 15 - 20O is maintained by adding ice and the pH range of 3 - 5 is maintained by adding sodium acetate. After stirring for 2 hours, the resulting yellow suspension is filtered off and the filter cake is washed in portions with 300 parts of water of 50 until neutral and free from salt. The crude dyestuff which is dried in a vacuum at 60 may be further purified by either recrystallisation or by column chromatography (eluant: toluene l ethyl methyl ketone).
The dyestuff thus obtained, has the following formula I
It dyes polyester (PES) fibres (PES 100%), as well as PES/Cotton (CO) mixed fabrics in brilliant, greenish-yellow shades having very good fastness, particularly wet fastness following thermo-fixation (180 , 30 mins).
may (Dimethylformamide, DMF) : 433 nm.
EXAMPLE 2 43.4 parts of the dyestuff of formula 2 with a titre of 958
obtained by the diazotization of p-aminobenzoic acid in diluted hydrochloric acid with 4N nitrite solution and coupling with the coupling component of example 1, are suspended in 125 parts of dimethylformamide, whilst adding 30.5 parts of an hydros K2CO3. 28 parts of monochloroacetic acid benzyl ester are subsequently added in drops at 60 - 65 , and the resultant yellow reaction suspension is stirred for 30 minutes. After diluting with 500 parts of 95% ethyl alcohol and cooling to 15 - 200, the precipitated dyestuff is filtered off by suction and washed with 200 parts of 95% ethyl alcohol of 10 - 15 and subsequently with 500 parts of water of 60". The dyestuff which is dried in a vacuum at 60 is structurally identical to that of example 1 and may similarly be purified by recrystallisation or by column chromatography (eluant: toluene / ethyl methyl ketone).
EXAMPLE 3
If 28.5 parts of the amine of formula 3
are used instead of 28.1 parts of 4-amino-benzoic acid-(l-carbobenzyloxy)-methyl-ester in example 1, and the process is otherwise as described in example 1, after working up, a dyestuff of formula 4 is obtained
In a manner analogous to the dyestuff of example 1 above, it dyes polyester (PES) fibres (PES 100%), as well as PES/Cotton (CO) mixed fabrics in brilliant, greenish-yellow shades having very good fastness, particularly wet fastness following thermo-fixation (180 , 30 mins).
Table 1 below, gives further dyestuffs of formula I, which are produced analogously to the procedures given in the preceding examples.
R is always R'-O-, R, is always hydrogen, with the exception of examples 41 and 42, where it is methyl.
Unless otherwise stated, all the alkyl and alkylene radicals are straight-chained, R2 is hydrogen and R3 is methyl.
All dyestuffs dye polyester fibre material in yellow shades with very good fastness.
TABLE 1
Ex. R R4 position of 4 No. ester (nm)
group DMF
4 -CH2C6H5 -C2H5 4'- 433
5 do. -C3H7 do. do.
6 do. H do. do.
7 do. -C5H11 do. do.
8 do. -C6H13 do. do.
9 do. -(CH2)3OC,Hg do. do.
10 do. -(CH2)3OCH(CH3)2 do. do.
11 do. -C3H7/-C4H9 (1:1) 3'- 429 12 do. do. 2'- 427 13 do. do. 4'- 432 14 -C,HsCI -C2H5 do. 433 15 do. -C3H7 do. do.
16 do. -C3H7/-C4H9 (1:1) do. do.
17 do. -C6H13 do. do.
18 do. -(CH2)3OC4H9 do. do.
19 do. -C3H7/-C4H9(1:1) 3'- 430 20 do. do. 2'- do.
21 -C3H6C1 -C3H7 /-C4H9 (1:1) 4'- 433 22 do. do. 3'- 430 23 -C3H6-C6H5 -C4H9 4'- 433 24 -CH2CH=CH-C6H5 -(CH2)3OC4H9 do. do.
25 -C2H40C6H5 -C4H9 do. do.
26 do. -(CH2)3OC4H9 do. do.
27 do. -C3H7/-C4H9 (1:1) 3'- 429
TABLE 1 / continuation
Ex. R R4 position of #max No. ester (nm)
group DMF 28 -C2H4-C6H5 -C3H, /-C4H9 (1:1) 4'- 433 29 -CH2CH=CH2 -(CH2)3OC4H, do. do.
30 -CH2C=CH do. do. do.
31 -C2H4OCH3 -C6Hl3 do. do.
32 -C2H4OC2H5 -(CH2)3 OC4H9 do. do.
33 do. -CH2C6H5 do. do.
34 -C2H4OC4H9 -C3H7/-C4H9-n (1:1) do. do.
35 -C6H5 do. do. do.
36 -CH2C6H5 -CH3 do. do.
37
do. do. do 38 - do. do. do.
39 do. do. do. do. do. do.
40 y do. do. do.
TABLE 1/continuation
41 CH24 -CH3 4' 432 42 -CH2C6H5 -CH2CH2Cl do. do.
43 do. -CH3 do. do.
44 -C2H4OC2H5 -(CH2)3 OC3H7 do. do.
EXAMPLE 45 25.5 parts of 4-amino-benzoic acid-(l -benzoyl)-methyl-ester are mixed vigorously in 30 parts of 30% hydrochloric acid, and after adding 25 parts of ice and 25 parts of water, a solution of 3.8 parts of sodium nitrite in 15 parts water is added at 5-10 over the course of 30 minutes. The mixture is stirred for 2 hours at 15-20 , the slight excess nitrous acid is broken down with amidosulphonic acid, and the mixture filtered until clear.The resultant diazonium salt solution is then dispensed continuously, whilst stirring, into a mixture of 9.7 parts of N-propyl- and 10.3 parts of N-butyl-3-cyano4-methyl-pyridone-2 in 100 parts of water at pH 7.5, whereby the coupling temperature is maintained at 15-20 by sprinkling in a little ice. A pH value of > 4 is maintained by adding ca. 5 parts of sodium acetate. After stirring for 2 hours, the pH is set at 5 with 30% caustic soda solution, the mixture is heated to ca. 75 , stirred for 1 hour and filtered. The yellow filter cake is washed in portions with warm water until free from salt, and dried in a vacuum at 60".
The dyestuff obtained corresponds to the following formula:
and dyes polyester fibre material in brilliant, greenish-yellow shades [#max = 433 (DMF)] with excellent fastness, in particular excellent wet fastness, after thermo-fixation (180 130 mins).
Table 2 gives further examples of yellow dyestuffs which can be produced e.g. in accordance with example 45. The dyestuffs correspond to the following formula
TABLE 2
Ex. No. R2 R4 shade position of #max ester group 46 H -CH, greenish-yellow 4' 433 47 H -C2H5 do. 4' do.
48 H -C,H7 do. 4' do.
49 H -C4H9 do. 4' do.
50 H -CH2CH(CH3)2 do. 4' do.
51 H -(CH2),OCH3 do. 4' do.
52 H -(CH2)3OC4H, do. 4' do.
53 H -(CH2)3OC2H5 do. 4' do.
54 H -NH2 greenish- 4' 433 yellow 55 55 H H do. 4' 432 56 H -C2H4OCH3 do. 4 433 57 H -C2H,OCOCH3 do. 4' do.
58 C1 -C3H7/-C4H9 (1:1) do. 4' do.
59 H do. do. 3' 430 60 H -C3H7/-C4H9 (1:1) do. 2' 428 61 H -(CH2),OCOCH3 do. 4' 433 Application Example 1 17.5 parts of the dyestuff according to example 1 in the form of the moist prcsscake are wet-ground by a known method with 325 parts of a commercial dispersing agent based on lignin sulphonates, and pulverized to a powder. 1.2 parts of this dye preparation are added to 2000 parts of demineralized water of 70 , which contains 40 parts of ammonium sulphate; the pH value of the dye bath is set at 5 with 85% formic acid. 100 parts of washed polyester fibre fabric are placed in this dye bath, the container is closed, heated to 1300 over the course of 20 minutes, and dyeing continues for a further 40 minutes at this temperature. After cooling, the polyester fibre fabric is removed from the dye bath, rinsed, soaped and cleansed by reduction with sodium hydrosulphite in the usual way. After thermo-fixation (180 , 30 mins), a brilliant yellow dyeing is obtained with very good allround fastness, especially fastness to light and sublimation, in particular excellent wet fastness. The dyestuff of examples 2 to 61 may be used in analogous manner, and brilliant yellow dyeings with very good all-round fastness are obtained.
Claims (10)
1. Monoazo disperse dyestuff of formula I
wherein R signifies phenyl, optionally substituted, or a group of formula R'-O-,
R' signifies C3-4-alkenyl, C3-4-alkynyl, phenyl, or C1-8-alkyl which bears
one or two substituents,
R, signifies hydrogen or C, 2-alkyl, R2 signifies hydrogen or halogen,
R3 signifies hydrogen or C1.3-alkyl, and
R4 signifies hydrogen, linear or branched C1-8-alkyl which optionally
bears one substituent, or an amino group which optionally bears one
substitutent,
the dyestuff being free from water-solubilizing groups, and mixtures thereof.
2. Dyestuff according to claim 1, wherein R4 is an unsubstituted linear or branched C,-6 alkyl radical.
3. Process for the production of a monoazo disperse dyestuff of formula I, according
to claim 1, characterized in that a diazotized amine of formula U
is coupled with an amine of formula m
R1, R2, R3 and R4 having the meanings given in claim 1 above.
4. Process for the production of a monoazo disperse dyestuff of formula I, according
to claim 1, characterized in that a compound of formula IV
is condensed with a compound of formula V
wherein Hal is a halogen atom and R , R2, R3 and R4 having the meanings given in
claim 1 above.
5. Use of the monoazo disperse dyestuff of formula I or mixtures thereof, according
to either claim 1 or 2, for dyeing or printing fibres or threads or materials produced
therefrom, which comprise fully or semi-synthetic, hydrophobic, organic materials.
6. Use of the monoazo disperse dyestuff of formula I or mixtures thereof, according
to either claim 1 or 2, for thermotiansfer printing.
7. Use of the monoazo disperse dyestuff of formula I or mixtures thereof, according
to claim 1 or 2, in a rapid-dyeing process.
8. Textile which has been dyed with a dyestuff of formula I or mixture thereof, as
claimed in either claim 1 or 2.
9. Monoazo disperse dyestuff according to either claim 1 or 2, obtainable by a
process according to claim 3.
10. Monoazo disperse dyestuff according to either claim 1 or 2, obtainable by a
process according to claim 4.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19518080 | 1995-05-17 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| GB9609994D0 GB9609994D0 (en) | 1996-07-17 |
| GB2300863A true GB2300863A (en) | 1996-11-20 |
| GB2300863B GB2300863B (en) | 1998-01-28 |
Family
ID=7762135
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB9609994A Expired - Fee Related GB2300863B (en) | 1995-05-17 | 1996-05-14 | Monoazo-dispersion dyestuffs |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JP3977457B2 (en) |
| KR (1) | KR100419691B1 (en) |
| CH (1) | CH690648A5 (en) |
| DE (1) | DE19618586B8 (en) |
| ES (1) | ES2117568B1 (en) |
| FR (1) | FR2734274B1 (en) |
| GB (1) | GB2300863B (en) |
| IT (1) | IT1284646B1 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009118260A1 (en) * | 2008-03-25 | 2009-10-01 | Dystar Textilfarben Gmbh & Co. Deutschland Kg | Azopyridone disperse dyes, their preparation and use |
| CN108276800A (en) * | 2018-02-01 | 2018-07-13 | 苏州科法曼化学有限公司 | A kind of disperse dye composition and its application |
| EP3715423A1 (en) | 2019-03-27 | 2020-09-30 | 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 |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4859254B2 (en) | 2006-11-30 | 2012-01-25 | キヤノン株式会社 | Dye compound and yellow toner containing the dye compound |
| JP2009280691A (en) * | 2008-05-22 | 2009-12-03 | Sumitomo Chemical Co Ltd | Azo compound and salt of the same |
| TWI526502B (en) * | 2009-12-25 | 2016-03-21 | Sumitomo Chemical Co | Pyridine ketone compound compounds |
| CN102746711B (en) * | 2012-07-10 | 2014-12-03 | 浙江昱泰染化科技有限公司 | Disperse dye composition, dye product and application thereof |
| CN102746712A (en) * | 2012-07-10 | 2012-10-24 | 浙江昱泰染化科技有限公司 | Disperse dye composition, dye product and application |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03166989A (en) * | 1989-11-28 | 1991-07-18 | Mitsui Toatsu Chem Inc | Yellow thermally sublimable transfer sheet |
| JPH04163093A (en) * | 1990-10-25 | 1992-06-08 | Mitsui Toatsu Chem Inc | Yellow color type thermal sublimation transfer sheet |
| EP0633296A1 (en) * | 1993-07-09 | 1995-01-11 | MITSUI TOATSU CHEMICALS, Inc. | Novel dyestuffs and their use |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1088895B (en) * | 1977-11-22 | 1985-06-10 | Acna | WATER-SOLUBLE MONOZOIC DYES |
| JPS6076564A (en) * | 1983-10-04 | 1985-05-01 | Mitsui Toatsu Chem Inc | Monoazo dye for synthetic fiber |
| JPH03175089A (en) * | 1989-12-05 | 1991-07-30 | Mitsui Toatsu Chem Inc | Color for sublimable thermal recording and transfer sheet |
-
1996
- 1996-04-30 FR FR9605532A patent/FR2734274B1/en not_active Expired - Fee Related
- 1996-05-08 CH CH01168/96A patent/CH690648A5/en not_active IP Right Cessation
- 1996-05-09 DE DE19618586A patent/DE19618586B8/en not_active Expired - Fee Related
- 1996-05-14 GB GB9609994A patent/GB2300863B/en not_active Expired - Fee Related
- 1996-05-16 ES ES09601095A patent/ES2117568B1/en not_active Expired - Fee Related
- 1996-05-16 KR KR1019960016422A patent/KR100419691B1/en not_active IP Right Cessation
- 1996-05-17 IT IT96RM000342A patent/IT1284646B1/en active IP Right Grant
- 1996-05-17 JP JP12351696A patent/JP3977457B2/en not_active Expired - Lifetime
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03166989A (en) * | 1989-11-28 | 1991-07-18 | Mitsui Toatsu Chem Inc | Yellow thermally sublimable transfer sheet |
| JPH04163093A (en) * | 1990-10-25 | 1992-06-08 | Mitsui Toatsu Chem Inc | Yellow color type thermal sublimation transfer sheet |
| EP0633296A1 (en) * | 1993-07-09 | 1995-01-11 | MITSUI TOATSU CHEMICALS, Inc. | Novel dyestuffs and their use |
Non-Patent Citations (2)
| Title |
|---|
| Chemical Abstracts, Vol. 115, abstr no 291173 & JP 03 166989 A * |
| Chemical Abstracts, Vol. 119, abstr no 105988 & JP 04 163093 A * |
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009118260A1 (en) * | 2008-03-25 | 2009-10-01 | Dystar Textilfarben Gmbh & Co. Deutschland Kg | Azopyridone disperse dyes, their preparation and use |
| CN101981132A (en) * | 2008-03-25 | 2011-02-23 | 德司达染料德国有限公司 | Azopyridone disperse dyes, their preparation and use |
| US8696766B2 (en) | 2008-03-25 | 2014-04-15 | Dystar Colours Deutschland Gmbh | Azopyridone disperse dyes, their preparation and use |
| CN101981132B (en) * | 2008-03-25 | 2014-06-04 | 德司达染料分销有限公司 | Azopyridone disperse dyes, their preparation and use |
| TWI465522B (en) * | 2008-03-25 | 2014-12-21 | Dystar Colours Distrib Gmbh | Azopyridone disperse dyes, their preparation and use |
| KR101547524B1 (en) | 2008-03-25 | 2015-08-26 | 다이스타 컬러스 디스트리뷰션 게엠베하 | Azopyridone disperse dyes, their preparation and use |
| CN108276800A (en) * | 2018-02-01 | 2018-07-13 | 苏州科法曼化学有限公司 | A kind of disperse dye composition and its application |
| CN108276800B (en) * | 2018-02-01 | 2019-11-19 | 苏州科法曼化学有限公司 | A kind of disperse dye composition and its application |
| EP3715423A1 (en) | 2019-03-27 | 2020-09-30 | 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 |
| WO2020193159A1 (en) | 2019-03-27 | 2020-10-01 | 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 |
| WO2020193160A1 (en) | 2019-03-27 | 2020-10-01 | 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 |
| US11479672B2 (en) | 2019-03-27 | 2022-10-25 | 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 |
| US11560480B2 (en) | 2019-03-27 | 2023-01-24 | 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| GB9609994D0 (en) | 1996-07-17 |
| ES2117568A1 (en) | 1998-08-01 |
| ITRM960342A1 (en) | 1997-11-17 |
| KR960041286A (en) | 1996-12-19 |
| JP3977457B2 (en) | 2007-09-19 |
| KR100419691B1 (en) | 2005-08-10 |
| ES2117568B1 (en) | 1999-07-01 |
| CH690648A5 (en) | 2000-11-30 |
| DE19618586B8 (en) | 2008-10-16 |
| GB2300863B (en) | 1998-01-28 |
| FR2734274A1 (en) | 1996-11-22 |
| JPH0925423A (en) | 1997-01-28 |
| DE19618586A1 (en) | 1996-11-21 |
| FR2734274B1 (en) | 1997-11-14 |
| DE19618586B4 (en) | 2008-07-17 |
| ITRM960342A0 (en) | 1996-05-17 |
| IT1284646B1 (en) | 1998-05-21 |
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| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 20150514 |