US3619104A - Process for the production of level end-uniform dyeings with water-soluble sulfuric acid esters of leuco-vat dyestuffs - Google Patents
Process for the production of level end-uniform dyeings with water-soluble sulfuric acid esters of leuco-vat dyestuffs Download PDFInfo
- Publication number
- US3619104A US3619104A US837332A US3619104DA US3619104A US 3619104 A US3619104 A US 3619104A US 837332 A US837332 A US 837332A US 3619104D A US3619104D A US 3619104DA US 3619104 A US3619104 A US 3619104A
- Authority
- US
- United States
- Prior art keywords
- sulfuric acid
- leuco
- acid esters
- parts
- padding
- 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
- 238000000034 method Methods 0.000 title claims abstract description 16
- 238000004043 dyeing Methods 0.000 title abstract description 29
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 title abstract description 17
- 238000004519 manufacturing process Methods 0.000 title abstract description 6
- 229920000151 polyglycol Polymers 0.000 claims abstract description 18
- 239000010695 polyglycol Substances 0.000 claims abstract description 18
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 229920000742 Cotton Polymers 0.000 abstract description 10
- 239000000203 mixture Substances 0.000 abstract description 6
- 239000000463 material Substances 0.000 abstract description 5
- 229920000728 polyester Polymers 0.000 abstract description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 4
- 239000004753 textile Substances 0.000 abstract description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 3
- 239000004744 fabric Substances 0.000 description 15
- 229920001223 polyethylene glycol Polymers 0.000 description 13
- 239000000975 dye Substances 0.000 description 12
- 239000002202 Polyethylene glycol Substances 0.000 description 9
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 6
- 239000000835 fiber Substances 0.000 description 5
- 235000013311 vegetables Nutrition 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- -1 aliphatic alcohols Chemical class 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229920001451 polypropylene glycol Polymers 0.000 description 3
- 235000010344 sodium nitrate Nutrition 0.000 description 3
- 239000004317 sodium nitrate Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- BZSXEZOLBIJVQK-UHFFFAOYSA-N 2-methylsulfonylbenzoic acid Chemical compound CS(=O)(=O)C1=CC=CC=C1C(O)=O BZSXEZOLBIJVQK-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- CMZUMMUJMWNLFH-UHFFFAOYSA-N sodium metavanadate Chemical compound [Na+].[O-][V](=O)=O CMZUMMUJMWNLFH-UHFFFAOYSA-N 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000010981 turquoise 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
- D06P1/22—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 vat dyestuffs including indigo
- D06P1/28—Esters of vat dyestuffs
-
- 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
- D06P1/44—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 insoluble pigments or auxiliary substances, e.g. binders
- D06P1/60—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 insoluble pigments or auxiliary substances, e.g. binders using compositions containing polyethers
- D06P1/613—Polyethers without nitrogen
- D06P1/6138—Polymerisation products of glycols, e.g. Carbowax, Pluronics
Definitions
- ABSTRACT A process for the production of consistently level and end-uniform dyeings on textile materials selected from the group consisting of cotton and of mixtures of cotton and polyesters by padding with sulfuric acid esters ofleuco-vat dyestuffs, wherein the padding is carried out in the presence of a polyglycol ofthe formula in which R is a member selected from the group consisting of hydrogen and methyl and .r is an integer, and which has an average molecular weight within the range of L000 to 20,000.
- the present invention is based on the observation that satisfactory, consistently level and end-uniform dyeings are obtained by using a padding bath containing a polyglycol of the formula HO-(CHRCH,O),-H in which R is a hydrogen atom or a methyl group, and x is a whole number, and which has a molecular weight within the range of l,000 to 10,000.
- polyglycols there are used polyethylene glycols or poly propylene glycols. There are also suitable mixtures of polyethylene and polypropylene glycols, and copolymers of ethylene oxide and propylene oxide. ln practice there are preferably used ordinary commercial mixtures of polyglycols having different molecular weights. Especially good results are obtained by using polyethylene glycols having average molecular weights within the range of from 1,000 to l0,000.
- the padding bath preferably contains, per liter, 0.5 to l0 grams of a polyglycol or polyglycols used in the invention. However, smaller or larger quantities may be used.
- the padding baths may contain the usual assistants. However, the addition of dispersing agents is not necessary.
- the padding may be carried out at various temperatures. and is preferably carried out at room temperature. Fluctuations in temperature do not adversely affect the end uniformity.
- the process of the invention is suitable for dyeing fabrics of vegetable fibers and also for dyeing mixed fabrics containing vegetable fibers.
- EXAMPLE 1 ln a bath containing. per L000 parts, 2 parts of the highly substantive dyestuff ofColor lndex (2nd Edition) No. 59,826, 5 parts of sodium nitrate and 2 parts of polyethylene glycol having an average molecular weight of 4.000, a cotton fabric is padded at room temperature with a squeezing effect of about percent. The material is then dried, developed continuously in a bath containing 3.4 percent of sulfuric acid, and
- polyethylene glycol having a molecular weight of 4,000 there may be used polyethylene glycols having molecular weights within the range of from 1,000 to 20,000 or a polypropylene glycol having a molecular weight of l,200.
- polyethylene glycol used is replaced by the same quantity of a polyethylene glycol having an average molecular weight of 200, there is obtained an effect that is considerably less favorable with respect to enduniformity.
- EXAMPLE 2 A solution containing, per [,000 parts, 5 parts of the dyestuff of Color Index No. 69,526, 0.3 part of the sulfuric acid ester of the leuco-vat dyestuff of French specification No. 1,037,4l9, 0.l part of the dyestuff of Color Index No.
- urea 50 parts of urea, 30 parts of an aqueous solution of 5 percent of the sodium salt of polymeric methacrylic acid, 2 parts of a polyethylene glycol having an average molecular weight of 4,000, 0.l part of sodium metavanadate, 8 parts of ammonium thiocyanate and 3 parts of sodium chlorate, is padded at room temperature onto 5,000 meters of a mixed fabric of polyester and cotton (67/33) with a squeezing effect of about 60 percent. After being dried, the mixed fabric is subjected for 1 minute to a dry heat treatment at 200 C., and then finished in the usual manner. The whole dyeing process is carried out in a fully continuous manner. There is obtained a level grey dyeing that, in spite of the differing substantivities of the dyestuffs, exhibits no change in the depth or shade of the dyeing.
- the padding bath used in this example has a considerably lower foaming capacity than a padding bath that contains 1 part of a condensation product of 1 mol of nonyl-phenol and l0 mols of ethylene oxide.
- EXAMPLE 3 In a padding bath containing, per 1,000 parts, 1 part of the highly substantive dyestuff of Color Index No. 59,826, 1 part of the dyestuff of Color Index No. 69,826 having a lower substantivity, 8 parts of sodium nitrate and 4 parts of a polyethylene glycol having an average molecular weight of 2,000, a cotton fabric is padded at 40 C. with a squeezing effect ofabout 80 percent. The dyeing is developed in a continuous manner as described in example 1. The turquoise dyeing exhibits no change in color from the beginning to the end.
- EXAMPLE 4 7.5 parts of the dyestufi' of Color Index No. 67,001, 3.5 part of the dyestuff obtainable according to example 8 of French Specification No. 1,167,704, 1.5 parts of the sodium salt of polymeric methacrylic acid and 2 parts of a polyethylene glycol having an average molecular weight of 4,000 are dissolved in 1,000 parts of water and padded at room temperature onto a mixed fabric of polyester and cotton (67/33) with a squeezing effect of about 60 percent. After being dried, the mixed fabric is subjected for 1 minute to a dry heat treatment at 200 C.
- the mixed fabric is passes for 3 seconds at room temperature through a bath containing 40 parts of 96 percent sulfuric acid and 1 part of sodium nitrate in 1,000 pans of water. Finally the dyeing is finished in the usual manner. The whole dyeing process is carried out in a fully continuous manner. There is obtained a fully level dyeing. Even when dyeing several thousands of meters of mixed fabric, no change in the depth or shade of the dyeing can be noticed. By using higher or different padding temperatures the levelness of the dyeing is not impaired.
- the dyeing is developed, after the dry-heat treatment, for 10 seconds at 60-70 C. is a dyebath containing 3 parts of sodium chlorate, 10 parts of 96 percent of sulfuric acid and 0.5 part of sodium metavanadate dissolved in 1,000 parts of water, excellent shades are also obtained.
- a process for the production of consistently level and end-uniform dyeings on textile materials selected from the group consisting of cotton and of mixtures of cotton and polyesters by padding with sulfuric acid esters of leuco-vat dyestuffs, wherein the padding is carried out is the presence of a polyglycol of the formula l-lO-(CHRCH,O),-H in which R is a member selected from the group consisting of hydrogen and methyl and x is an integer, and which has an average molecular weight within the range of 1,000 to 20,000.
- polyglycol has an average molecular weight within the range of 1,000 to 10,000.
- R is hydrogen and the polyglycol has an average molecular weight within the range of 1,000 to 10,000 and wherein the polyglycol is present in concentration within the range of 0.5 to 10 grams per liter.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH966968A CH524722A (de) | 1968-06-28 | 1968-06-28 | Verfahren zur Herstellung egaler, endengleicher Färbungen mit wasserlöslichen Leukoschwefelsäureestern von Küpenfarbstoffen auf cellulosehaltigen Textilmaterialien |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3619104A true US3619104A (en) | 1971-11-09 |
Family
ID=4354417
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US837332A Expired - Lifetime US3619104A (en) | 1968-06-28 | 1969-06-27 | Process for the production of level end-uniform dyeings with water-soluble sulfuric acid esters of leuco-vat dyestuffs |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3619104A (en, 2012) |
| BE (1) | BE735254A (en, 2012) |
| CH (2) | CH966968A4 (en, 2012) |
| DE (1) | DE1932502B2 (en, 2012) |
| ES (1) | ES368888A1 (en, 2012) |
| FR (1) | FR2014360A1 (en, 2012) |
| GB (1) | GB1250108A (en, 2012) |
| NL (1) | NL6909912A (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3864077A (en) * | 1971-09-02 | 1975-02-04 | Bayer Ag | Non-Aqueous Dyestuffs with a Phthalic Acid Dialkyl Ester |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2930756A1 (de) * | 1979-07-28 | 1981-02-26 | Cassella Ag | Klotzhilfsmittel und verfahren zum faerben von cellulosefasern bzw. gemischen von cellulosefasern zusammen mit synthesefasern mit schwefel-, schwefelkuepen-, kuepen- und reaktivfarbstoffen |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2965678A (en) * | 1951-12-28 | 1960-12-20 | Gen Aniline & Film Corp | Polyoxyethylene ethers of branched chain alcohols |
| US2992062A (en) * | 1955-11-25 | 1961-07-11 | Gen Aniline & Film Corp | Dyeing synthetics with soluble leuco ester salts |
| US3512915A (en) * | 1960-05-13 | 1970-05-19 | Dow Corning | Dyeing textile with a dye solution containing a copolymer of an alkyl siloxane and a polyaminoalkylsiloxane having at least 3 carbons in the alkyl chain |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2592852A (en) * | 1948-04-09 | 1952-04-15 | Bancroft & Sons Co J | Process of producing dyed lustrous printed pattern effects using acidcuring resins and free leuco bases of vat dyes |
-
1968
- 1968-06-28 CH CH966968D patent/CH966968A4/xx unknown
- 1968-06-28 CH CH966968A patent/CH524722A/de not_active IP Right Cessation
-
1969
- 1969-06-25 FR FR6921280A patent/FR2014360A1/fr not_active Withdrawn
- 1969-06-26 DE DE19691932502 patent/DE1932502B2/de active Granted
- 1969-06-27 US US837332A patent/US3619104A/en not_active Expired - Lifetime
- 1969-06-27 ES ES368888A patent/ES368888A1/es not_active Expired
- 1969-06-27 BE BE735254D patent/BE735254A/xx unknown
- 1969-06-27 GB GB1250108D patent/GB1250108A/en not_active Expired
- 1969-06-27 NL NL6909912A patent/NL6909912A/xx not_active Application Discontinuation
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2965678A (en) * | 1951-12-28 | 1960-12-20 | Gen Aniline & Film Corp | Polyoxyethylene ethers of branched chain alcohols |
| US2992062A (en) * | 1955-11-25 | 1961-07-11 | Gen Aniline & Film Corp | Dyeing synthetics with soluble leuco ester salts |
| US3512915A (en) * | 1960-05-13 | 1970-05-19 | Dow Corning | Dyeing textile with a dye solution containing a copolymer of an alkyl siloxane and a polyaminoalkylsiloxane having at least 3 carbons in the alkyl chain |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3864077A (en) * | 1971-09-02 | 1975-02-04 | Bayer Ag | Non-Aqueous Dyestuffs with a Phthalic Acid Dialkyl Ester |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1932502A1 (de) | 1970-01-02 |
| GB1250108A (en, 2012) | 1971-10-20 |
| NL6909912A (en, 2012) | 1969-12-30 |
| FR2014360A1 (en, 2012) | 1970-04-17 |
| BE735254A (en, 2012) | 1969-12-01 |
| CH966968A4 (en, 2012) | 1972-03-15 |
| DE1932502B2 (de) | 1976-06-16 |
| CH524722A (de) | 1972-03-15 |
| ES368888A1 (es) | 1971-05-16 |
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