US3294474A - Method of dyeing cellulosic textiles with mixtures of thiosulfonic acidsulfur dyes and reactive dyes and compositions thereof - Google Patents
Method of dyeing cellulosic textiles with mixtures of thiosulfonic acidsulfur dyes and reactive dyes and compositions thereof Download PDFInfo
- Publication number
- US3294474A US3294474A US415819A US41581964A US3294474A US 3294474 A US3294474 A US 3294474A US 415819 A US415819 A US 415819A US 41581964 A US41581964 A US 41581964A US 3294474 A US3294474 A US 3294474A
- Authority
- US
- United States
- Prior art keywords
- reactive
- dyeing
- sulfur
- dyes
- dyestuff
- 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.)
- Expired - Lifetime
Links
- 239000000975 dye Substances 0.000 title claims description 37
- 238000004043 dyeing Methods 0.000 title claims description 27
- 239000000203 mixture Substances 0.000 title claims description 16
- 239000004753 textile Substances 0.000 title claims description 16
- 238000000034 method Methods 0.000 title claims description 13
- 239000000985 reactive dye Substances 0.000 title 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 25
- 239000011593 sulfur Substances 0.000 claims description 25
- 229910052717 sulfur Inorganic materials 0.000 claims description 25
- 239000000463 material Substances 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 9
- 239000003638 chemical reducing agent Substances 0.000 claims description 9
- 150000001447 alkali salts Chemical class 0.000 claims description 7
- 230000000694 effects Effects 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 238000011282 treatment Methods 0.000 claims description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
- 239000003513 alkali Substances 0.000 description 7
- 229910000029 sodium carbonate Inorganic materials 0.000 description 6
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 6
- 229920000742 Cotton Polymers 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 235000013351 cheese Nutrition 0.000 description 5
- 239000000835 fiber Substances 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 230000001590 oxidative effect Effects 0.000 description 3
- 229960001922 sodium perborate Drugs 0.000 description 3
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 3
- RTLULCVBFCRQKI-UHFFFAOYSA-N 1-amino-4-[3-[(4,6-dichloro-1,3,5-triazin-2-yl)amino]-4-sulfoanilino]-9,10-dioxoanthracene-2-sulfonic acid Chemical compound C1=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=C(S(O)(=O)=O)C=C1NC(C=1)=CC=C(S(O)(=O)=O)C=1NC1=NC(Cl)=NC(Cl)=N1 RTLULCVBFCRQKI-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 241000083869 Polyommatus dorylas Species 0.000 description 2
- KXXFHLLUPUAVRY-UHFFFAOYSA-J [Na+].[Na+].[Na+].[Cu++].[O-]C(=O)C1=CC=C(C=C1N=N[C-](N=NC1=C([O-])C(NC2=NC(F)=NC(NCCOCCS(=O)(=O)C=C)=N2)=CC(=C1)S([O-])(=O)=O)C1=CC=CC=C1)S([O-])(=O)=O Chemical compound [Na+].[Na+].[Na+].[Cu++].[O-]C(=O)C1=CC=C(C=C1N=N[C-](N=NC1=C([O-])C(NC2=NC(F)=NC(NCCOCCS(=O)(=O)C=C)=N2)=CC(=C1)S([O-])(=O)=O)C1=CC=CC=C1)S([O-])(=O)=O KXXFHLLUPUAVRY-UHFFFAOYSA-J 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- -1 acryloyl- Chemical group 0.000 description 2
- BMAUDWDYKLUBPY-UHFFFAOYSA-L disodium;3-[[4-[(4,6-dichloro-1,3,5-triazin-2-yl)amino]-2-methylphenyl]diazenyl]naphthalene-1,5-disulfonate Chemical compound [Na+].[Na+].C=1C=C(N=NC=2C=C3C(=CC=CC3=C(C=2)S([O-])(=O)=O)S([O-])(=O)=O)C(C)=CC=1NC1=NC(Cl)=NC(Cl)=N1 BMAUDWDYKLUBPY-UHFFFAOYSA-L 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 125000005179 haloacetyl group Chemical group 0.000 description 2
- UJMBCXLDXJUMFB-UHFFFAOYSA-K trisodium;5-oxo-1-(4-sulfonatophenyl)-4-[(4-sulfonatophenyl)diazenyl]-4h-pyrazole-3-carboxylate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)C1=NN(C=2C=CC(=CC=2)S([O-])(=O)=O)C(=O)C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 UJMBCXLDXJUMFB-UHFFFAOYSA-K 0.000 description 2
- YXZRCLVVNRLPTP-UHFFFAOYSA-J turquoise blue Chemical compound [Na+].[Na+].[Na+].[Na+].[Cu+2].NC1=NC(Cl)=NC(NC=2C=C(NS(=O)(=O)C3=CC=4C(=C5NC=4NC=4[N-]C(=C6C=CC(=CC6=4)S([O-])(=O)=O)NC=4NC(=C6C=C(C=CC6=4)S([O-])(=O)=O)NC=4[N-]C(=C6C=CC(=CC6=4)S([O-])(=O)=O)N5)C=C3)C(=CC=2)S([O-])(=O)=O)=N1 YXZRCLVVNRLPTP-UHFFFAOYSA-J 0.000 description 2
- 240000007124 Brassica oleracea Species 0.000 description 1
- SGHZXLIDFTYFHQ-UHFFFAOYSA-L Brilliant Blue Chemical compound [Na+].[Na+].C=1C=C(C(=C2C=CC(C=C2)=[N+](CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=2C(=CC=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S([O-])(=O)=O)=C1 SGHZXLIDFTYFHQ-UHFFFAOYSA-L 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 229960001506 brilliant green Drugs 0.000 description 1
- HXCILVUBKWANLN-UHFFFAOYSA-N brilliant green cation Chemical compound C1=CC(N(CC)CC)=CC=C1C(C=1C=CC=CC=1)=C1C=CC(=[N+](CC)CC)C=C1 HXCILVUBKWANLN-UHFFFAOYSA-N 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- KMUONIBRACKNSN-UHFFFAOYSA-N potassium dichromate Chemical compound [K+].[K+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KMUONIBRACKNSN-UHFFFAOYSA-N 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000988 sulfur dye Substances 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/30—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using sulfur dyes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/58—Material containing hydroxyl groups
- D06P3/60—Natural or regenerated cellulose
- D06P3/66—Natural or regenerated cellulose using reactive dyes
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/916—Natural fiber dyeing
- Y10S8/918—Cellulose textile
Definitions
- This invention relates to dye compositions and methods of dyeing cellulosic textile materials therewith, and more particularly to dye compositions comprising as the principal constituents the alkali salts of thiosulfonic acids of sulfur dyestuffs, an alkali, a reducing agent for said sulfur dyestuffs and a reactive dyestuff as defined herein, said composition being capable of dyeing said textile materials in a single dye bath under controlled temperature conditions with good uniformity of color.
- the dyestuff compositions of the present invention have simplified the dyeing operation and produced bet ter dyeing results with the combination of the sulfur dyestuffs and the reactive dyestuffs used in a single bath. This has been made possible by using the water soluble alkali salts of thiosulfonic acids of sulfur dyestuffs, instead of the usual sulfur dyestuffs, and by using an alkali that effects fixation of the reactive dyestufi and concurrently using a reducing agent that effects fixation of the sulfur dystuff onto the textile fiber.
- the textile material to be treated in accordance with this invention may be in any of the usual forms, such as fibers, yarns, and woven or knitted fabrics.
- the basic fiber of this material may be any of the presently known cellulosic textile fibers, e.g. cotton, rayon, linen.
- cellulosic constituents in blends or mixed fabrics may be dyed satisfactorily by the dyestutf compositions of this invention.
- any of the commonly known reactive dyestuffs may be employed, such as for example those with haloacetyl-, B-halopropionyb, acryloyl-, and fi-phenylsulfonylpropionyl-amino groups.
- Particularly suitable are reactive dyestuffs containing as a reactive residue a halotriazine-, halopyrimidine-, or halopyridazine residue, or the residue of a halopyridazineor haloquinoxaline-carboxylic acid.
- a suitable reducing agent such as for example sodium sulfide or sodium hydrosulfide
- a presently advantageous procedure for carrying out the dyeing process of the present invention comprises treating the cellulosic material to be dyed in a first step with dye liquors containing as an essential component, aside from the water-soluble alkali salt of the thiosulfonic acid of the sulfur dyestutf and the reactive dyestuff, only alkali which gives rise to the fixation of the reactive dyestuif, and then further treating at an elevated temperature, after the addition of the reducing agent necessary for the reduction of the sulfur dyestuff.
- the sulfur dyestuff goes onto the fiber, and after the usual finishing, full combination dyeings are obtained, having a very good uniformity.
- Example 1 A cotton cheese is processed in a circulating liquor containing 5% Hydrosol Fast Yellow-brown GL (C.I. Solubilized Sulfur Brown 60, C.I. No. 53326), 2% Procion-yellow M-RS (C.I. Reactive Yellow 4), 20 g./l. calcined sodium sulfate, and 10 g./l. sodium carbonate, during 45 minutes at 30 C. Then 7.5% of a 20% sodium hydrosulfide solution are added, dyeing is continued for a further 10 minutes at 30 C. and, after increasing the temperature of the liquor to C., for a further 30 minutes at this temperature. Subsequently, the material is rinsed, oxidized at 40 C. with a liquor containing 1 g./l. sodium perborate, soaped, and rinsed again. A deep yellow-brown dyeing of good uniformity is thus obtained.
- Hydrosol Fast Yellow-brown GL C.I. Solubilized Sulfur Brown 60, C.I
- Example 2 A cotton cheese is first treated in a circulating bath containing 5% Hydrosol Blue FFG (C.I. Solubilized Sulfur Blue 2, C.I. No. 53481), 2% Cibacron Turquoiseblue G (C.I. Reactive Blue 7 constitution described in Collection Czechoslov. Chem. Commun, vol. 25 (1960), page 2797), 20 g./l. calcined sodium sulfate, 20 g./l.
- Hydrosol Blue FFG C.I. Solubilized Sulfur Blue 2, C.I. No. 53481
- Cibacron Turquoiseblue G C.I. Reactive Blue 7 constitution described in Collection Czechoslov. Chem. Commun, vol. 25 (1960), page 2797
- Example 3 A cotton cheese is treated in a circulating bath containing 3% Hydrosol Blue R (C.I. Solubilized Sulfur Blue 7, C.I. No. 53441), and 2% Procion Brillitant-blue MRS (C.I. Reactive Blue 4), 30 g./l. calcined sodium sulfate, and 15 g./l. calcined sodium carbonate during 30 minutes at 30 C.; then 4.5% of a 20% sodium hydrosulfide solution are added, the material is dyed for a further 10 minutes at 30 C. and, after the temperature of the liquor has been raised to 60 C., another 30 minutes at this temperature. Subsequently, the dyeing is rinsed, oxidized at 40 C. with 0.5% of 35% hydrogen peroxide, soaped, and rinsed again. Thus, a deep and brilliant blue dyeing of a good uniformity is obtained.
- Hydrosol Blue R C.I. Solubilized Sulfur Blue 7, C.I. No. 53441
- Example 4 A cheese of mixed cotton-cellulose yarn is first treated in a circulating bath containing 10% Hydrosol Fast Yellow G (C.I. Solubilized Sulfur Yellow 5 being the thiosulfonic acid of C.I. Sulfur Yellow 5, the constitution of which is described in Collection Czechoslov. Chem. Commun., vol. 27 (1962), page 1533/48), 2% Cibacron Turquoise-blue G (C.I. Reactive Blue 7, constitution described in Collection Czechoslov. Chem. Commun., vol 25 (1960), page 2797), 20 g./l. calcined sodium sulfate, 2% sodium sulfhydrate, and g./l. calcined sodium carbonate, during 10 minutes at 30 C.
- Hydrosol Fast Yellow G C.I. Solubilized Sulfur Yellow 5 being the thiosulfonic acid of C.I. Sulfur Yellow 5 being the constitution of which is described in Collection Czechoslov. Chem. Commun.,
- the temperature of the liquor is then increased to 90 C. within 30 minutes, and the material is dyed during 30 minutes at this temperature. Subsequently, the dyeing is finished by rinsing, oxidizing at 40 C. with a liquor containing 1 g./l. sodium perborate, soaping and rinsing. A brilliant green dyeing is, thus, obtained which is impossible to obtain with sulfur dyes only.
- Example 5 A cotton cheese is treated in a circulating bath containing 6% Hydrosol Fast Yellow-brown GL (C.I. Solubilized Sulfur Brown 60, Cl. No. 5326), 2% Cibacron Scarlet 2G (C.I. Reactive Red 9, constitution described in Collection Czechoslov. Chem. Commun., vol 25 (1960), page 2794/95), 30 g./l. calcined sodium sulfate, and g./l. calcined sodium carbonate during 60 minutes at 60-65 C. The dye liquor is then cooled down to 30 C., admixed with 2% sodium hydrosulfide, and dyeing is continued for 10 minutes at 30 C.
- 6% Hydrosol Fast Yellow-brown GL C.I. Solubilized Sulfur Brown 60, Cl. No. 5326
- Cibacron Scarlet 2G C.I. Reactive Red 9
- a dyestutf composition for dyeing cellulosic textile materials comprising as the principal constituents a water soluble alkali salt of a thiosulfonic acid of a sulfur dyestuff, an alkali, a reducing agent for said sulfur dyestuff, and a reactive dyestulf, said composition being capable of dyeing said textile materials in a single dye bath under controlled temperature conditions with good uniformity of color.
- halopyrimidine-, halopyridazine residue, a halopyridazineand haloquinoxaline-carboxylic acid residue is a halopyrimidine-, halopyridazine residue, a halopyridazineand haloquinoxaline-carboxylic acid residue.
- a method of dyeing cellulosic textile materials comprising subjecting the textile materials to a single dye bath containing as a dye composition therein a water soluble alkali salt of a thiosulfonic acid group-containing sulfur dyestuff, an alkali, a reducing agent for the sulfur dyestulf, and a reactive dyestuff, for a period of time to effect dyeing thereof; then subjecting the dyed material to the usual finishing treatments.
- a method as defined in claim 4 wherein said reducing agent for the sulfur dyestuffs comprises an alkali sulfide.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC31623A DE1276596B (de) | 1963-12-07 | 1963-12-07 | Verfahren zum einbadigen Faerben von Cellulosematerialien mit Reaktivfarbstoffen und Schwefelfarbstoffen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3294474A true US3294474A (en) | 1966-12-27 |
Family
ID=7019918
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US415819A Expired - Lifetime US3294474A (en) | 1963-12-07 | 1964-12-03 | Method of dyeing cellulosic textiles with mixtures of thiosulfonic acidsulfur dyes and reactive dyes and compositions thereof |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3294474A (de) |
| BE (1) | BE656777A (de) |
| CH (1) | CH423712A (de) |
| DE (1) | DE1276596B (de) |
| GB (1) | GB1026250A (de) |
| NL (1) | NL6413895A (de) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6019800A (en) * | 1998-12-17 | 2000-02-01 | Clariant Finance (Bvi) Limited | Process and composition of sulfur dyes |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3097908A (en) * | 1960-03-16 | 1963-07-16 | Hoechst Ag | Dyeings and prints possessing fastness to wet processing and their manufacture on cellulose materials and protein fibers |
| US3113824A (en) * | 1963-12-10 | Dyeing with sulfur dyes |
-
1963
- 1963-12-07 DE DEC31623A patent/DE1276596B/de active Pending
-
1964
- 1964-11-30 NL NL6413895A patent/NL6413895A/xx unknown
- 1964-12-03 US US415819A patent/US3294474A/en not_active Expired - Lifetime
- 1964-12-04 GB GB49416/64A patent/GB1026250A/en not_active Expired
- 1964-12-04 CH CH1567864A patent/CH423712A/de unknown
- 1964-12-07 BE BE656777D patent/BE656777A/xx unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3113824A (en) * | 1963-12-10 | Dyeing with sulfur dyes | ||
| US3097908A (en) * | 1960-03-16 | 1963-07-16 | Hoechst Ag | Dyeings and prints possessing fastness to wet processing and their manufacture on cellulose materials and protein fibers |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6019800A (en) * | 1998-12-17 | 2000-02-01 | Clariant Finance (Bvi) Limited | Process and composition of sulfur dyes |
Also Published As
| Publication number | Publication date |
|---|---|
| NL6413895A (de) | 1965-06-08 |
| BE656777A (de) | 1965-04-01 |
| CH423712A (de) | 1966-07-29 |
| DE1276596B (de) | 1968-09-05 |
| GB1026250A (en) | 1966-04-14 |
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