EP0660894B1 - Procede de teinture et d'impression de matieres textiles en fibres de cellulose, en presence de cetones hydroxy alpha - Google Patents
Procede de teinture et d'impression de matieres textiles en fibres de cellulose, en presence de cetones hydroxy alpha Download PDFInfo
- Publication number
- EP0660894B1 EP0660894B1 EP93919295A EP93919295A EP0660894B1 EP 0660894 B1 EP0660894 B1 EP 0660894B1 EP 93919295 A EP93919295 A EP 93919295A EP 93919295 A EP93919295 A EP 93919295A EP 0660894 B1 EP0660894 B1 EP 0660894B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- dyeing
- cellulose fibers
- liquor
- cyclic
- fibers
- 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
- 238000004043 dyeing Methods 0.000 title claims abstract description 55
- 239000000463 material Substances 0.000 title claims abstract description 24
- 238000000034 method Methods 0.000 title claims abstract description 20
- 239000004753 textile Substances 0.000 title claims abstract description 19
- 229920003043 Cellulose fiber Polymers 0.000 title claims abstract description 16
- 125000004122 cyclic group Chemical group 0.000 title description 8
- 239000000975 dye Substances 0.000 claims abstract description 26
- 239000003638 chemical reducing agent Substances 0.000 claims abstract description 19
- 239000000203 mixture Substances 0.000 claims abstract description 12
- 239000000835 fiber Substances 0.000 claims abstract description 10
- 150000001923 cyclic compounds Chemical class 0.000 claims abstract description 6
- 239000012736 aqueous medium Substances 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 60
- XLSMFKSTNGKWQX-UHFFFAOYSA-N hydroxyacetone Chemical compound CC(=O)CO XLSMFKSTNGKWQX-UHFFFAOYSA-N 0.000 description 20
- 239000000984 vat dye Substances 0.000 description 17
- 229920000742 Cotton Polymers 0.000 description 13
- 230000000052 comparative effect Effects 0.000 description 11
- JAJIPIAHCFBEPI-UHFFFAOYSA-N 9,10-dioxoanthracene-1-sulfonic acid Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2S(=O)(=O)O JAJIPIAHCFBEPI-UHFFFAOYSA-N 0.000 description 10
- 238000004040 coloring Methods 0.000 description 10
- 229920001577 copolymer Polymers 0.000 description 10
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 4
- RYYXDZDBXNUPOG-UHFFFAOYSA-N 4,5,6,7-tetrahydro-1,3-benzothiazole-2,6-diamine;dihydrochloride Chemical compound Cl.Cl.C1C(N)CCC2=C1SC(N)=N2 RYYXDZDBXNUPOG-UHFFFAOYSA-N 0.000 description 4
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 4
- 230000001590 oxidative effect Effects 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 150000004056 anthraquinones Chemical class 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- QTWZICCBKBYHDM-UHFFFAOYSA-N leucomethylene blue Chemical compound C1=C(N(C)C)C=C2SC3=CC(N(C)C)=CC=C3NC2=C1 QTWZICCBKBYHDM-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- 239000011976 maleic acid Substances 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- 238000004048 vat dyeing Methods 0.000 description 3
- GCDBEYOJCZLKMC-UHFFFAOYSA-N 2-hydroxyanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(O)=CC=C3C(=O)C2=C1 GCDBEYOJCZLKMC-UHFFFAOYSA-N 0.000 description 2
- 235000000177 Indigofera tinctoria Nutrition 0.000 description 2
- 229920000297 Rayon Polymers 0.000 description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 2
- 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 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 229940097275 indigo Drugs 0.000 description 2
- COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229920002401 polyacrylamide Polymers 0.000 description 2
- 239000000988 sulfur dye Substances 0.000 description 2
- 239000002351 wastewater Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 150000004057 1,4-benzoquinones Chemical class 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- POPBYCBXVLHSKO-UHFFFAOYSA-N 9,10-dioxoanthracene-1-carboxylic acid Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C(=O)O POPBYCBXVLHSKO-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
- 229920001407 Modal (textile) Polymers 0.000 description 1
- 229930192627 Naphthoquinone Natural products 0.000 description 1
- 229920002845 Poly(methacrylic acid) Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- AFPRJLBZLPBTPZ-UHFFFAOYSA-N acenaphthoquinone Chemical class C1=CC(C(C2=O)=O)=C3C2=CC=CC3=C1 AFPRJLBZLPBTPZ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001717 carbocyclic compounds Chemical class 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 150000004338 hydroxy anthraquinones Chemical class 0.000 description 1
- 238000009981 jet dyeing Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003094 perturbing effect Effects 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- GUEIZVNYDFNHJU-UHFFFAOYSA-N quinizarin Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=CC=C2O GUEIZVNYDFNHJU-UHFFFAOYSA-N 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 239000001226 triphosphate Substances 0.000 description 1
- 235000011178 triphosphate Nutrition 0.000 description 1
- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing Methods 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
- D06P1/44—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
- D06P1/64—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 low-molecular-weight organic compounds without sulfate or sulfonate groups
- D06P1/651—Compounds without nitrogen
- D06P1/65106—Oxygen-containing compounds
- D06P1/65118—Compounds containing hydroxyl groups
-
- 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
- D06P1/221—Reducing systems; Reducing catalysts
-
- 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
- D06P1/64—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 low-molecular-weight organic compounds without sulfate or sulfonate groups
- D06P1/651—Compounds without nitrogen
- D06P1/65106—Oxygen-containing compounds
- D06P1/65112—Compounds containing aldehyde or ketone groups
-
- 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
- EP-A-0 364 752 discloses a process for dyeing textile materials made from cellulose fibers with vat dyes in an alkaline medium, in which mixtures of sodium dithionite and / or thiourea dioxide and ⁇ -hydroxycarbonyl compounds, such as hydroxyacetone, are used as reducing agents, and the dyeing at pH values of at least 13 and at temperatures above 75 ° C. The dyeing is then completed in the usual way by oxidizing and washing the colored material.
- the a-hydroxycarbonyl compounds described therein, such as hydroxyacetone are not sufficiently stable under the dyeing conditions and are converted into a multitude of products in a confusing manner, which, among other things, lead to odor problems.
- the cellulose fibers are dyed with viable dyes, such as vat dyes, in particular indigo, or sulfur dyes.
- viable dyes such as vat dyes, in particular indigo, or sulfur dyes.
- the vat dyes are either indigo or anthraquinone or indigoide dyes.
- Vat dyes and sulfur dyes have been commercially available for a long time and are documented in the Color Index (C.I.), cf. Color Index, 3rd edition 1971, volume 3, pages 3719 to 3844, and volume 4, C.I. 58000 to 74000, Soc. Dyers and Colorists, England.
- the cyclic ⁇ -hydroxyketones with structure I can optionally be used with all reducing agents known for dyeing vat dyes, e.g. in a mixture with sodium dithionite and / or thiourea dioxide.
- the weight ratio of the cyclic ⁇ -hydroxyketones to sodium dithionite and / or thiourea dioxide to be used according to the invention in such reducing agent mixtures is, for example, 1: 1 to 1:15, preferably 1: 2 to 1:10.
- the color depth corresponds to a comparative dyeing which is obtained by the known IN method by dyeing the same material with a dye liquor which contained 18 ml / l sodium hydroxide solution at 38 ° Bé and 6 g / l sodium dithionite and in which the dyeing took place within 45 min 60 ° C was carried out.
- Example 2 was repeated with the only exception that the cotton jersey was dyed with a liquor which now contained 3 g / l of hydroxyacetone as reducing agent instead of the ⁇ -hydroxycyclohexanone. A level, rub-fast and wash-fast green dyeing was obtained which was about 50% weaker in color than the dyeing according to Example 2.
- Example 3 is repeated with a dyeing liquor containing 0.5 g / l of the blue vat dye of CI no. 60015 (Vat Blue 26), 30 ml / l NaOH 38 ° Bé and 3 g / l hydroxyacetone. A level, rub-fast and wash-fast blue dyeing is obtained which is about 50% weaker in color than the dyeing according to Example 3.
- the textile is then impregnated at room temperature with 100% of its weight with a liquor which contains 30 g / l of ⁇ -hydroxycyclopentanone and 100 ml / l of NaOH 38 ° Bé and then treated in a steamer at 102 ° C within one minute. It is then rinsed with cold water, oxidized for 3 minutes with 3 ml / l of hydrogen peroxide, rinsed and soaped at 98 ° C. for 5 minutes. You get a level, rub and wash-fast green color. This reaches the color depth of a comparative dyeing after the usual one Continuous process with a liquor containing 100 ml / l NaOH 38 ° Bé and 60 g / l sodium dithionite.
- the dyeing reaches the color depth of a comparative dyeing, in which the reduction of the vat dye is carried out using a chemical liquor which contains 100 ml / l NaOH 38 ° Bé and 60 g / l sodium dithionite.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Coloring (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Claims (5)
- Procédé de teinture et d'impression de matières textiles, qui se composent de fibres de cellulose, ou qui contiennent des fibres de cellulose en mélange à d'autres fibres, en milieu aqueux, à des valeurs de pH supérieures à 12, avec des colorants allant en cuve et en présence d'au moins un agent réducteur pour les colorants allant en cuve et apprêtage de la teinture de la manière habituelle, caractérisé en ce que, à titre d' agents réducteurs, on utilise des composés cycliques qui contiennent au moins une fois l'unité de structure suivante
dans le cycle de la molécule. - Procédé suivant la revendication 1, caractérisé en ce que l'on utilise les composés cycliques en proportions de 1 à 10 g/litre de bain.
- Procédé suivant la revendication 1 ou 2, caractérisé en ce que l'on utilise l'α-hydroxycyclohexanone à titre d'agent réducteur.
- Procédé suivant la revendication 1 ou 2, caractérisé en ce que l'on utilise l'α-hydroxycyclopentanone à titre d'agent réducteur.
- Procédé suivant l'une quelconque des revendications 1 à 4, caractérisé en ce que l'on entreprend la teinture complémentairement en présence de composés quinoïdaux qui sont solubles dans l'eau dans les conditions de la teinture.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4230870 | 1992-09-16 | ||
| DE4230870A DE4230870A1 (de) | 1992-09-16 | 1992-09-16 | Verfahren zum Färben und Bedrucken von textilen Materialien aus Cellulosefasern |
| PCT/EP1993/002424 WO1994006961A1 (fr) | 1992-09-16 | 1993-09-08 | Procede de teinture et d'impression de matieres textiles en fibres de cellulose, en presence de cetones hydroxy alpha |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0660894A1 EP0660894A1 (fr) | 1995-07-05 |
| EP0660894B1 true EP0660894B1 (fr) | 1996-03-20 |
Family
ID=6468017
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP93919295A Expired - Lifetime EP0660894B1 (fr) | 1992-09-16 | 1993-09-08 | Procede de teinture et d'impression de matieres textiles en fibres de cellulose, en presence de cetones hydroxy alpha |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US5558677A (fr) |
| EP (1) | EP0660894B1 (fr) |
| JP (1) | JPH08501354A (fr) |
| AT (1) | ATE135766T1 (fr) |
| DE (2) | DE4230870A1 (fr) |
| DK (1) | DK0660894T3 (fr) |
| ES (1) | ES2084508T3 (fr) |
| WO (1) | WO1994006961A1 (fr) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW251325B (fr) * | 1993-03-30 | 1995-07-11 | Basf Ag | |
| IT1271814B (it) * | 1994-12-28 | 1997-06-09 | Alpi Spa | Tintura di fogli di legno mediante coloranti appartenenti alla classe "al tino". |
| DE19712649C1 (de) * | 1997-03-26 | 1998-06-18 | Wella Ag | Mittel und Verfahren zur Färbung keratinischer Fasern |
| DE10010060A1 (de) * | 2000-03-02 | 2001-09-06 | Dystar Textilfarben Gmbh & Co | Mediatorsysteme auf Basis gemischter Metallkomplexe zur Reduktion von Farbstoffen |
| DE10010059A1 (de) * | 2000-03-02 | 2001-09-06 | Dystar Textilfarben Gmbh & Co | Mediatorsysteme auf Basis gemischter Metallkomplexe zur Reduktion von Farbstoffen |
| DE102004014764A1 (de) * | 2004-03-26 | 2005-10-06 | Wella Ag | Haarfärbemittel mit Küpenfarbstoffen |
| CN101349016B (zh) * | 2007-07-20 | 2010-05-26 | 上海市毛麻纺织科学技术研究所 | 染料复合还原剂及采用该复合还原剂染色的方法 |
| US11618981B2 (en) * | 2016-08-01 | 2023-04-04 | Wilana Chemical LLC | Nylon floorcoverings employing vat dyestuffs and methods of making the same |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2164463C3 (de) * | 1971-12-24 | 1978-07-13 | Basf Ag, 6700 Ludwigshafen | Verfahren und Mittel zum Färben und Bedrucken von Textilien mit Küpenfarbstoffen |
| US3883249A (en) * | 1972-05-15 | 1975-05-13 | Timothy R Pryor | Z-factor and other diffractographic displacement and profile sensors |
| JPS57191382A (en) * | 1981-05-14 | 1982-11-25 | Mitsui Toatsu Chemicals | Treatment of dyed article by indanethrone vat dye |
| CH680180B5 (fr) * | 1988-07-29 | 1993-01-15 | Ciba Geigy Ag | |
| DE3833194A1 (de) * | 1988-09-30 | 1990-04-05 | Basf Ag | Verfahren zum faerben von textilen materialien aus cellulosefasern |
| DE4103639A1 (de) * | 1991-02-07 | 1992-08-13 | Basf Ag | Verfahren zum faerben von textilen materialien aus cellulosefasern |
-
1992
- 1992-09-16 DE DE4230870A patent/DE4230870A1/de not_active Withdrawn
-
1993
- 1993-09-08 AT AT93919295T patent/ATE135766T1/de not_active IP Right Cessation
- 1993-09-08 WO PCT/EP1993/002424 patent/WO1994006961A1/fr not_active Ceased
- 1993-09-08 EP EP93919295A patent/EP0660894B1/fr not_active Expired - Lifetime
- 1993-09-08 US US08/379,433 patent/US5558677A/en not_active Expired - Fee Related
- 1993-09-08 DE DE59301994T patent/DE59301994D1/de not_active Expired - Lifetime
- 1993-09-08 ES ES93919295T patent/ES2084508T3/es not_active Expired - Lifetime
- 1993-09-08 JP JP6507760A patent/JPH08501354A/ja active Pending
- 1993-09-08 DK DK93919295.1T patent/DK0660894T3/da active
Also Published As
| Publication number | Publication date |
|---|---|
| WO1994006961A1 (fr) | 1994-03-31 |
| DE59301994D1 (de) | 1996-04-25 |
| ATE135766T1 (de) | 1996-04-15 |
| DK0660894T3 (da) | 1996-04-15 |
| EP0660894A1 (fr) | 1995-07-05 |
| ES2084508T3 (es) | 1996-05-01 |
| US5558677A (en) | 1996-09-24 |
| JPH08501354A (ja) | 1996-02-13 |
| DE4230870A1 (de) | 1994-03-17 |
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