CA2081639A1 - Blue reactive dyestuff mixture having improved compatibility - Google Patents
Blue reactive dyestuff mixture having improved compatibilityInfo
- Publication number
- CA2081639A1 CA2081639A1 CA 2081639 CA2081639A CA2081639A1 CA 2081639 A1 CA2081639 A1 CA 2081639A1 CA 2081639 CA2081639 CA 2081639 CA 2081639 A CA2081639 A CA 2081639A CA 2081639 A1 CA2081639 A1 CA 2081639A1
- Authority
- CA
- Canada
- Prior art keywords
- dyestuff
- reactive dyestuff
- reactive
- mixture according
- parts
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 239000000975 dye Substances 0.000 title claims abstract description 49
- 239000000203 mixture Substances 0.000 title claims abstract description 29
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims abstract description 5
- 150000004056 anthraquinones Chemical class 0.000 claims abstract description 5
- 239000002253 acid Substances 0.000 claims abstract description 4
- 238000004043 dyeing Methods 0.000 claims description 11
- 229920003043 Cellulose fiber Polymers 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 229910004727 OSO3H Inorganic materials 0.000 claims description 3
- 239000000835 fiber Substances 0.000 claims description 3
- 125000000129 anionic group Chemical group 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 239000000872 buffer Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 229910017053 inorganic salt Inorganic materials 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 239000002270 dispersing agent Substances 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000000306 component Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 230000006399 behavior Effects 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- 229910006069 SO3H Inorganic materials 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000985 reactive dye Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- -1 sulpho, carboxyl Chemical group 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
-
- 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
- C09B67/004—Mixtures of two or more reactive dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
Blue reactive dyestuff mixture having improved compatibility A b s t r a c t Mixtures based on a triphendioxazine dyestuff of the formula (I.1) or (I.2) (I.1) (1.2) Le A 28 728 - Foreign Countries and an anthraquinone dyestuff which, in the form of the free acid, has the formula (II) (II) in which the substituents have the meaning given in the description, show improved compatibility with other dyestuffs.
Le A 28 728 - Foreign Countries
Le A 28 728 - Foreign Countries
Description
The invention relates to a blue reactive dyestuff mixture of two blue reactive dyestuffs of the same hue which, in the dyeing of cellulose fibres or cellulose fibre blends, has an improved compatibility behaviour compared with the individual components.
Reactive dyestuffs are used in the form of their indivi-dual components or in the form of combinations with other dyestuffs of different hues, the fixation yield of a eomponent in the combination being expected to give the same fixation yield as the dyeing of the individual com-ponents by themselve~ given an identical total dyestuff content of the dye liquor. The triphendioxazine dyestuffs described in DE-A-3,439,756 are very useful dyestuffs.
~owever, when combined with the red and yellow reactive dyestuffs necessary for producing fashionable shade~ they show in some cases a reduced yield, 80 that a dichromatic dyeing may exhibit a shift towards the shade of the combination dyestuff and the blue portion in trichromatic dyeings may be reduced.
The object of the invention is to improve the u~e of such dyestuffs in combinations.
~he pre~ent invention relates to a mixture of a triphen-dioxazine reactive dyestuff, an anthraquinone reactive dyestuff and, if desired, further dyestuffs, charac-terised in that the triphendioxazine dye~tuff, ~n the Le A 28 728 - 1 -form of the free acid, has the formula (I.1) or (I.2) L-Y~-XI ~ x~-r~-L (I.1) j Z-25 R2 .'~
C l S03H
X2J~N0~x2 (I.2) 2 SO3H Cl 1 2 N~lN N~N
Ha 1 1~N~ ~Y~Ha I
tS03H) 1-~ tS03H) 1-3 in which S Rl, R2 are H or a ~ubstituent, in particular Cl or Br, X1-X3 are, independently of one another, NR3, O, S, R3 is H, substituted or unsubstituted Cl-C~-alkyl, Le A 28 728 - 2 -- 208~639 yl, y2 are, independently of one another, alkylene, in particular C2-C6-alkylene, which may be substi-tuted or interrupted in the alkylene chain by hetero atom~, Z i3 -CH-CH2 or -CH2-CH2-W in which W denotes a radical which can be eliminated with the formation of the group -CH=CH2, for example -OSO3H, -SSO3H or -OPO3H2, -O-acyl, in particular -O-Cl-C4-alkylcarbonyl, it being possible for the rings A to contain, if desired, further customary ~ubstituents, each L i8, independently of. the other, a water-solubilising group, in particular sulpho, carboxyl and sulphato, Hal is F, Cl and the anthraquinone reactive dye~tuff, .in the form of the free acid has the formula (II) 03H (II) O Nlt--Q
S02CH2CH2-O-sOIH
Preferred compounds I.l have the formula ~e A 28 728 - 3 -203163~
Rl S2 Z
H03SO-Yl-xl ~
~ ~ X1-Y1-0503H
in which the substituents have the meaning given.
Particular preference i~ given to:
Ho350_y1_ ~ ~ ~Ia) ~ H-Y1-0503H
in which R1, R2 and y1 have the abovementioned meaning and Z denotes -CH2-CH2-OSO3H or -CH=CH2, in particular Cl H03SO-Y -H ~ ~
~ -Y1-0503H
~0350-CH2-cH2-o2s C 1 (Ib) Le A 28 728 - 4 -2081~3~
in which yl is C2-C4-alkylene.
A very particularly preferred dyestuff has the following formula (Ic) Cl 502-CH2-cH2-0so3H
H03SO-CH2-CH2 HN ~ ~
~ ~NH-CH2-CH2-OSO~H
H03SO-CH2-C~2-02s Cl (Ic) Further preferred compounds have the formula (Id) _y1-NH (Id) HN-Y3-N~ o~ f =
f =o S2-Z R2 Y2 cooM
in which Rl, R2 are Cl y~ y2~ y3~ y4 are, independently of one another, an alkylene group having 2 to 6 C atoms, in particular of the formula (Ie) Le A 28 728 - 5 -20~163~
l 02H
12~4 - C-O
H03SO-~ H2-CH2 NH
Cl 2H4 (1~) 12H4 Cl 12 NH CH2-C~2-S3H
C - o Preferred compounds I.2 have the following formulae:
Le A 28 728 - 6 -208163~
~3r' ~ ~ k ~ I
S~
U
N
~ X
X U
Z
Reactive dyestuffs are used in the form of their indivi-dual components or in the form of combinations with other dyestuffs of different hues, the fixation yield of a eomponent in the combination being expected to give the same fixation yield as the dyeing of the individual com-ponents by themselve~ given an identical total dyestuff content of the dye liquor. The triphendioxazine dyestuffs described in DE-A-3,439,756 are very useful dyestuffs.
~owever, when combined with the red and yellow reactive dyestuffs necessary for producing fashionable shade~ they show in some cases a reduced yield, 80 that a dichromatic dyeing may exhibit a shift towards the shade of the combination dyestuff and the blue portion in trichromatic dyeings may be reduced.
The object of the invention is to improve the u~e of such dyestuffs in combinations.
~he pre~ent invention relates to a mixture of a triphen-dioxazine reactive dyestuff, an anthraquinone reactive dyestuff and, if desired, further dyestuffs, charac-terised in that the triphendioxazine dye~tuff, ~n the Le A 28 728 - 1 -form of the free acid, has the formula (I.1) or (I.2) L-Y~-XI ~ x~-r~-L (I.1) j Z-25 R2 .'~
C l S03H
X2J~N0~x2 (I.2) 2 SO3H Cl 1 2 N~lN N~N
Ha 1 1~N~ ~Y~Ha I
tS03H) 1-~ tS03H) 1-3 in which S Rl, R2 are H or a ~ubstituent, in particular Cl or Br, X1-X3 are, independently of one another, NR3, O, S, R3 is H, substituted or unsubstituted Cl-C~-alkyl, Le A 28 728 - 2 -- 208~639 yl, y2 are, independently of one another, alkylene, in particular C2-C6-alkylene, which may be substi-tuted or interrupted in the alkylene chain by hetero atom~, Z i3 -CH-CH2 or -CH2-CH2-W in which W denotes a radical which can be eliminated with the formation of the group -CH=CH2, for example -OSO3H, -SSO3H or -OPO3H2, -O-acyl, in particular -O-Cl-C4-alkylcarbonyl, it being possible for the rings A to contain, if desired, further customary ~ubstituents, each L i8, independently of. the other, a water-solubilising group, in particular sulpho, carboxyl and sulphato, Hal is F, Cl and the anthraquinone reactive dye~tuff, .in the form of the free acid has the formula (II) 03H (II) O Nlt--Q
S02CH2CH2-O-sOIH
Preferred compounds I.l have the formula ~e A 28 728 - 3 -203163~
Rl S2 Z
H03SO-Yl-xl ~
~ ~ X1-Y1-0503H
in which the substituents have the meaning given.
Particular preference i~ given to:
Ho350_y1_ ~ ~ ~Ia) ~ H-Y1-0503H
in which R1, R2 and y1 have the abovementioned meaning and Z denotes -CH2-CH2-OSO3H or -CH=CH2, in particular Cl H03SO-Y -H ~ ~
~ -Y1-0503H
~0350-CH2-cH2-o2s C 1 (Ib) Le A 28 728 - 4 -2081~3~
in which yl is C2-C4-alkylene.
A very particularly preferred dyestuff has the following formula (Ic) Cl 502-CH2-cH2-0so3H
H03SO-CH2-CH2 HN ~ ~
~ ~NH-CH2-CH2-OSO~H
H03SO-CH2-C~2-02s Cl (Ic) Further preferred compounds have the formula (Id) _y1-NH (Id) HN-Y3-N~ o~ f =
f =o S2-Z R2 Y2 cooM
in which Rl, R2 are Cl y~ y2~ y3~ y4 are, independently of one another, an alkylene group having 2 to 6 C atoms, in particular of the formula (Ie) Le A 28 728 - 5 -20~163~
l 02H
12~4 - C-O
H03SO-~ H2-CH2 NH
Cl 2H4 (1~) 12H4 Cl 12 NH CH2-C~2-S3H
C - o Preferred compounds I.2 have the following formulae:
Le A 28 728 - 6 -208163~
~3r' ~ ~ k ~ I
S~
U
N
~ X
X U
Z
3: ~ O ~
N N
U U
0~
O ~ 0~ U~
ot~
Le A 28 728 - 7 -2081~39 In a preferred embodiment of the invention 10 to 90% by weight of I and 90 to 10% by weight of II, in particular 30 to 70 parts of dyestuff I and 70 to 30 parts of dyestuf II, are present, relative to the mixture of dyestuff~ I and II.
The mixture according to the invention of dyestuffs I and II surprisingly produce~ an exhaust and fixation curve which are very sLmilar to those of the two individual components and thus result~ in a type of tinctorial behaviour which is very clo~e to that of the two individual dyestuffs. ~owever, the mixture according to the invention when combined with a third dyestuff is distinctly less degre~3ive than the dyestuff of the formula tI) and produces the same fixation yield as without admixing of foreign dyestuffs.
For explanation, see Fig. 1:
where the fixation curve (fixation time in minutes versus amount of dyestuff fixed on the fibre in per cent of final fixation) i9 plotted. Curve Ic shows the course of fixation for dyestuff Ic by itself, curve II the course of fixation for dyestuff II by itself and the solid line the course of fixation of a 50:50 mixture of Ic and II.
The shape of the curve show~ that the colouristic beha-viour of the individual dyestuffs becomes similar in the mixture, re~ulting in a new dyestuff having a uniform new fixation curve.
Le A 28 728 - 8 -2 ~ 3 ~
~he claimed dyestuff mixture is suitable in particular for the dyeing of cellulose fibres and blend~ thereof by any dyeing process for dyestuff I. A preferred application consists in dyeing at 60C by the following S dyeing scheme:
Time (min.) Temperature (C~ Measure 30C addition of sodium bicarbonate 30C addition of NaCl or Na2SO4 / 20-60 g/l 30C addition of ~odium carbonate, 10-20 g/l 45-75 heating to 60C ~tanding at 60C
The dyestuff mixture can contain customary additives;
preferably, it contains 1 to 50 parts of an inorganic salt, 1 to 5 parts by weight of an inorganic buffer, 0.5 to 10 parts of an organic anionic disper~ant and 0.5 to 5 parts of a dustproofing agent per 100 parts by weight of reactive dyestuff mixture.
~ample 1 100 parts of a knitted cotton fabric are treated at 30C
with 1000 parts of an aqueous dye liquor containing, in dissolved form:
2 parts of the reactive dyestuff mixture of 1 part of the Le A 28 728 - 9 -208~639 dyestuff Ic, 1 part of the dye~tuff III of the formula ~ ' ~ H2-S03H
NH ~OH
CI~ ~H3 F~
and 1 part of the dyestuff II
1/2 part of sodium bicarbonate 50 parts of sodium chloride and 15 part~ of sodium carbonate.
After uniform distribution of the dyestuff on the fibre material at 30C over a period of 45 minute~, the liquor i8 heated to 60C over a period of 30 minutes, and dyeing 0 iB continued for another 30 minutes while vigorously agitating the material in the liquor. The liquor ia then di~charged, and the dyed material i8 rinsed twice at 50C
and once at 80C.
The bath ia then filled with fresh liquor, heated to 98C, and the material i~ treated at thi~ temperature for 15 minutes. After cooling, a clear green dyeing having good fastness properties is obtained.
Le A 28 728 - 10 -
N N
U U
0~
O ~ 0~ U~
ot~
Le A 28 728 - 7 -2081~39 In a preferred embodiment of the invention 10 to 90% by weight of I and 90 to 10% by weight of II, in particular 30 to 70 parts of dyestuff I and 70 to 30 parts of dyestuf II, are present, relative to the mixture of dyestuff~ I and II.
The mixture according to the invention of dyestuffs I and II surprisingly produce~ an exhaust and fixation curve which are very sLmilar to those of the two individual components and thus result~ in a type of tinctorial behaviour which is very clo~e to that of the two individual dyestuffs. ~owever, the mixture according to the invention when combined with a third dyestuff is distinctly less degre~3ive than the dyestuff of the formula tI) and produces the same fixation yield as without admixing of foreign dyestuffs.
For explanation, see Fig. 1:
where the fixation curve (fixation time in minutes versus amount of dyestuff fixed on the fibre in per cent of final fixation) i9 plotted. Curve Ic shows the course of fixation for dyestuff Ic by itself, curve II the course of fixation for dyestuff II by itself and the solid line the course of fixation of a 50:50 mixture of Ic and II.
The shape of the curve show~ that the colouristic beha-viour of the individual dyestuffs becomes similar in the mixture, re~ulting in a new dyestuff having a uniform new fixation curve.
Le A 28 728 - 8 -2 ~ 3 ~
~he claimed dyestuff mixture is suitable in particular for the dyeing of cellulose fibres and blend~ thereof by any dyeing process for dyestuff I. A preferred application consists in dyeing at 60C by the following S dyeing scheme:
Time (min.) Temperature (C~ Measure 30C addition of sodium bicarbonate 30C addition of NaCl or Na2SO4 / 20-60 g/l 30C addition of ~odium carbonate, 10-20 g/l 45-75 heating to 60C ~tanding at 60C
The dyestuff mixture can contain customary additives;
preferably, it contains 1 to 50 parts of an inorganic salt, 1 to 5 parts by weight of an inorganic buffer, 0.5 to 10 parts of an organic anionic disper~ant and 0.5 to 5 parts of a dustproofing agent per 100 parts by weight of reactive dyestuff mixture.
~ample 1 100 parts of a knitted cotton fabric are treated at 30C
with 1000 parts of an aqueous dye liquor containing, in dissolved form:
2 parts of the reactive dyestuff mixture of 1 part of the Le A 28 728 - 9 -208~639 dyestuff Ic, 1 part of the dye~tuff III of the formula ~ ' ~ H2-S03H
NH ~OH
CI~ ~H3 F~
and 1 part of the dyestuff II
1/2 part of sodium bicarbonate 50 parts of sodium chloride and 15 part~ of sodium carbonate.
After uniform distribution of the dyestuff on the fibre material at 30C over a period of 45 minute~, the liquor i8 heated to 60C over a period of 30 minutes, and dyeing 0 iB continued for another 30 minutes while vigorously agitating the material in the liquor. The liquor ia then di~charged, and the dyed material i8 rinsed twice at 50C
and once at 80C.
The bath ia then filled with fresh liquor, heated to 98C, and the material i~ treated at thi~ temperature for 15 minutes. After cooling, a clear green dyeing having good fastness properties is obtained.
Le A 28 728 - 10 -
Claims (9)
1. Reactive dyestuff mixture containing at least one triphendioxazine reactive dyestuff, and at least one anthraquinone reactive dyestuff characterised in that the triphendioxazine dyestuff, in the form of the free acid, has the formula (I.1) or (I.2) (I.1) (I.2) in which Le A 28 728- US - 11 -R1, R2 are H or a substituent customary in tri-phendioxazine dyestuffs, R3 is H, substituted or unsubstituted C1-C4-alkyl, Hal is Cl, F, X1-X3 are, independently of one another, NR3, O, S, Y1,Y2 are, independently of one another, alkyl-ene, in particular C2-C6-alkylene, which may be substituted or interrupted in the alkylene chain by hetero atoms, Z is -CH=CH2 or -CH2-CH2-W in which W denotes radical which can be eliminated with the formation of the group -CH=CH2, each L is, independently of the other, a water-solubilising group, it being possible for the rings A to contain, if desired, further customary substituents, and in that the anthraquinone reactive dyestuff has the following formula (II) Le A 28 728 - 12 - (II)
2. Reactive dyestuff mixture according to Claim 1, characterised in that the compound (I) has the following formula in which the substituents have the meaning given in Claim 1.
3. Reactive dyestuff mixture according to Claim 1, characterised in that the compound I has the follow-ing formula (Ia) (Ia) Le A 28 728 - 13 -in which R1, R2 and Y have the abovementioned meaning and Z denotes -CH2-CH2-OSO3H or -CH=CH2.
4. Reactive dyestuff mixture according to Claim 1, characterised in that the dyestuff (I) has the following formula (Ib) (Ib) in which Y is C2-C4-alkylene.
5. Reactive dyestuff mixture according to Claim 1, characterised in that the dyestuff I has the follow-ing formula (Ic) or (Ie) (Ic) Le A 28 728 - 14 - (Ie)
6. Reactive dyestuff mixture according to Claim 1 , characterised in that 10 to 90% by weight of dyestuff I and 90 to 10% by weight of dyestuff II are present, relative to the mixture of dyestuffs I and II.
7. Reactive dyestuff mixture according to Claim 1 , characterised in that the dyestuff mixture contains 1 to 50 parts of an inorganic salt, 1 to 5 parts by weight of an inorganic buffer, 0.5 to 10 parts of an organic anionic dispersant and 0.5 to 5 parts of a dustproofing agent per 100 parts by weight of reactive dyestuff mixture.
Le A 28 728 - 15 -
Le A 28 728 - 15 -
8. Reactive dyestuff mixture according to Claim 1 , characterised in that it is present as a liquid brand.
9. Process for the dyeing of cellulose fibres and fibre blends containing cellulose fibres, characterised in that a reactive dyestuff mixture according to Claim 1 is used.
Le A 28 728 - 16 -
Le A 28 728 - 16 -
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19914135846 DE4135846C1 (en) | 1991-10-31 | 1991-10-31 | |
| DEP4135846.5 | 1991-10-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2081639A1 true CA2081639A1 (en) | 1993-05-01 |
Family
ID=6443782
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 2081639 Abandoned CA2081639A1 (en) | 1991-10-31 | 1992-10-28 | Blue reactive dyestuff mixture having improved compatibility |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP0539836A3 (en) |
| JP (1) | JPH05247369A (en) |
| CA (1) | CA2081639A1 (en) |
| DE (1) | DE4135846C1 (en) |
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|---|---|---|---|---|
| CN106336368A (en) * | 2016-08-24 | 2017-01-18 | 天津德凯化工股份有限公司 | Dye intermediate and preparation method thereof |
| CN106349127A (en) * | 2016-08-24 | 2017-01-25 | 天津德凯化工股份有限公司 | Novel dye intermediate and active dye prepared from dye intermediate |
| CN106349129A (en) * | 2016-08-24 | 2017-01-25 | 天津德凯化工股份有限公司 | Dye intermediate and active dye prepared from intermediate |
| CN106349747A (en) * | 2016-08-24 | 2017-01-25 | 天津德凯化工股份有限公司 | Blue active dye with high alkali resistance and preparation method of blue active dye |
| CN106349128A (en) * | 2016-08-24 | 2017-01-25 | 天津德凯化工股份有限公司 | Novel dye intermediate and active dye prepared from dye intermediate |
| CN106366025A (en) * | 2016-08-24 | 2017-02-01 | 天津德凯化工股份有限公司 | Dye intermediate (3-beta-hydroxyethylsulfonyl)aniline-4-aminoacetic acid and preparation method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5456726A (en) * | 1992-12-22 | 1995-10-10 | Sumitomo Chemical Company, Limited | Reactive dye composition and method for dyeing or printing cellulose fiber material using the same |
| JPH06192589A (en) * | 1992-12-22 | 1994-07-12 | Sumitomo Chem Co Ltd | Reactive dye mixture and method for dyeing or printing cellulose-based fiber material using the same |
| US8038736B2 (en) * | 2010-03-03 | 2011-10-18 | Dystar L.P. | Mixtures of fiber-reactive azo dyes |
| CN102504593B (en) * | 2011-10-13 | 2013-11-06 | 上海雅运纺织化工股份有限公司 | Blue dye composition and use thereof for fiber dyeing |
| CN108690373A (en) * | 2018-05-17 | 2018-10-23 | 泰兴市臻庆化工有限公司 | A kind of reactive dye mixture and preparation method thereof |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3111488A1 (en) * | 1981-03-24 | 1982-10-07 | Hoechst Ag, 6000 Frankfurt | LIQUID AND SOLID PREPARATIONS OF WATER-SOLUBLE FIBER REACTIVE DYES AND THEIR USE FOR COLORING OR PRINTING FIBER MATERIALS |
| DE3439756A1 (en) * | 1984-02-11 | 1985-08-14 | Bayer Ag, 5090 Leverkusen | TRIPHENDIOXAZINE VINYL SULPHONE DYES |
| JPH0676561B2 (en) * | 1985-07-16 | 1994-09-28 | 住友化学工業株式会社 | Liquid aqueous composition of reactive dye |
| DE3542025A1 (en) * | 1985-11-28 | 1987-06-11 | Hoechst Ag | MIXTURES OF WATER SOLUBLE FIBER REACTIVE DYES AND THEIR USE FOR COLORING |
| CH673465A5 (en) * | 1986-12-10 | 1990-03-15 | Sandoz Ag | |
| DE3703732A1 (en) * | 1987-02-07 | 1988-08-18 | Bayer Ag | METHOD FOR PRODUCING A CONCENTRATED AQUEOUS REACTIVE DYE SOLUTION |
| DE3852154T2 (en) * | 1987-07-22 | 1995-05-11 | Mitsubishi Chem Ind | Water-soluble dye mixture and dyeing process. |
-
1991
- 1991-10-31 DE DE19914135846 patent/DE4135846C1/de not_active Expired - Fee Related
-
1992
- 1992-10-20 EP EP19920117869 patent/EP0539836A3/en not_active Withdrawn
- 1992-10-27 JP JP4310798A patent/JPH05247369A/en active Pending
- 1992-10-28 CA CA 2081639 patent/CA2081639A1/en not_active Abandoned
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106336368A (en) * | 2016-08-24 | 2017-01-18 | 天津德凯化工股份有限公司 | Dye intermediate and preparation method thereof |
| CN106349127A (en) * | 2016-08-24 | 2017-01-25 | 天津德凯化工股份有限公司 | Novel dye intermediate and active dye prepared from dye intermediate |
| CN106349129A (en) * | 2016-08-24 | 2017-01-25 | 天津德凯化工股份有限公司 | Dye intermediate and active dye prepared from intermediate |
| CN106349747A (en) * | 2016-08-24 | 2017-01-25 | 天津德凯化工股份有限公司 | Blue active dye with high alkali resistance and preparation method of blue active dye |
| CN106349128A (en) * | 2016-08-24 | 2017-01-25 | 天津德凯化工股份有限公司 | Novel dye intermediate and active dye prepared from dye intermediate |
| CN106366025A (en) * | 2016-08-24 | 2017-02-01 | 天津德凯化工股份有限公司 | Dye intermediate (3-beta-hydroxyethylsulfonyl)aniline-4-aminoacetic acid and preparation method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| DE4135846C1 (en) | 1993-02-18 |
| EP0539836A3 (en) | 1993-09-15 |
| JPH05247369A (en) | 1993-09-24 |
| EP0539836A2 (en) | 1993-05-05 |
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