CH525997A - Method for reserving textile fiber material made from synthetic polyamides - Google Patents
Method for reserving textile fiber material made from synthetic polyamidesInfo
- Publication number
- CH525997A CH525997A CH942967A CH942967A CH525997A CH 525997 A CH525997 A CH 525997A CH 942967 A CH942967 A CH 942967A CH 942967 A CH942967 A CH 942967A CH 525997 A CH525997 A CH 525997A
- Authority
- CH
- Switzerland
- Prior art keywords
- reservation
- fiber material
- dyed
- nylon
- fiber
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 14
- 239000004952 Polyamide Substances 0.000 title claims description 11
- 239000002657 fibrous material Substances 0.000 title claims description 11
- 229920002647 polyamide Polymers 0.000 title claims description 11
- 239000004753 textile Substances 0.000 title claims description 9
- 150000001875 compounds Chemical group 0.000 claims description 22
- 239000000463 material Substances 0.000 claims description 16
- 239000000975 dye Substances 0.000 claims description 8
- 238000005470 impregnation Methods 0.000 claims description 7
- 125000000129 anionic group Chemical group 0.000 claims description 6
- 238000004043 dyeing Methods 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 239000000981 basic dye Substances 0.000 claims description 4
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 4
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- -1 threads Substances 0.000 description 13
- 229920002292 Nylon 6 Polymers 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000001488 sodium phosphate Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 229920002302 Nylon 6,6 Polymers 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000004677 Nylon Substances 0.000 description 4
- 235000010443 alginic acid Nutrition 0.000 description 4
- 229920000615 alginic acid Polymers 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229920001778 nylon Polymers 0.000 description 4
- 239000002562 thickening agent Substances 0.000 description 4
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 3
- PLDUPXSUYLZYBN-UHFFFAOYSA-N Fluphenazine Chemical compound C1CN(CCO)CCN1CCCN1C2=CC(C(F)(F)F)=CC=C2SC2=CC=CC=C21 PLDUPXSUYLZYBN-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- 229940072056 alginate Drugs 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 3
- 229910000397 disodium phosphate Inorganic materials 0.000 description 3
- 235000019800 disodium phosphate Nutrition 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 229960001374 fluphenazine decanoate Drugs 0.000 description 3
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 3
- 235000019799 monosodium phosphate Nutrition 0.000 description 3
- JLFNLZLINWHATN-UHFFFAOYSA-N pentaethylene glycol Chemical compound OCCOCCOCCOCCOCCO JLFNLZLINWHATN-UHFFFAOYSA-N 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 229920000571 Nylon 11 Polymers 0.000 description 2
- 229920000577 Nylon 6/66 Polymers 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- TZYHIGCKINZLPD-UHFFFAOYSA-N azepan-2-one;hexane-1,6-diamine;hexanedioic acid Chemical compound NCCCCCCN.O=C1CCCCCN1.OC(=O)CCCCC(O)=O TZYHIGCKINZLPD-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229920000591 gum Polymers 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- ODCNAEMHGMYADO-UHFFFAOYSA-N 1,4-dichlorophthalazine Chemical class C1=CC=C2C(Cl)=NN=C(Cl)C2=C1 ODCNAEMHGMYADO-UHFFFAOYSA-N 0.000 description 1
- SPSSDDOTEZKOOV-UHFFFAOYSA-N 2,3-dichloroquinoxaline Chemical compound C1=CC=C2N=C(Cl)C(Cl)=NC2=C1 SPSSDDOTEZKOOV-UHFFFAOYSA-N 0.000 description 1
- MHOFGBJTSNWTDT-UHFFFAOYSA-M 2-[n-ethyl-4-[(6-methoxy-3-methyl-1,3-benzothiazol-3-ium-2-yl)diazenyl]anilino]ethanol;methyl sulfate Chemical compound COS([O-])(=O)=O.C1=CC(N(CCO)CC)=CC=C1N=NC1=[N+](C)C2=CC=C(OC)C=C2S1 MHOFGBJTSNWTDT-UHFFFAOYSA-M 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920001612 Hydroxyethyl starch Polymers 0.000 description 1
- 229920000161 Locust bean gum Polymers 0.000 description 1
- 229920000305 Nylon 6,10 Polymers 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 229940105329 carboxymethylcellulose Drugs 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000000986 disperse dye Substances 0.000 description 1
- 238000010016 exhaust dyeing Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 229940071826 hydroxyethyl cellulose Drugs 0.000 description 1
- 229940050526 hydroxyethylstarch Drugs 0.000 description 1
- 235000010420 locust bean gum Nutrition 0.000 description 1
- 239000000711 locust bean gum Substances 0.000 description 1
- 239000000434 metal complex dye Substances 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 239000002759 woven fabric 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
- D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
- D06P5/12—Reserving parts of the material before dyeing or printing ; Locally decreasing dye affinity by chemical means
-
- 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
- D06P1/642—Compounds containing nitrogen
- D06P1/6426—Heterocyclic compounds
-
- 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
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/06—Material containing basic nitrogen containing amide groups using acid 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
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/24—Polyamides; Polyurethanes
- D06P3/241—Polyamides; Polyurethanes using acid 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
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/24—Polyamides; Polyurethanes
- D06P3/242—Polyamides; Polyurethanes using basic 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
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/24—Polyamides; Polyurethanes
- D06P3/26—Polyamides; Polyurethanes using dispersed 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
- 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
- D06P3/70—Material containing nitrile groups
- D06P3/74—Material containing nitrile groups using acid 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
- D06P3/79—Polyolefins
- D06P3/791—Polyolefins using acid 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
- Y10S8/917—Wool or silk
-
- 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
- Y10S8/92—Synthetic fiber dyeing
- Y10S8/924—Polyamide fiber
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Dispersion Chemistry (AREA)
- Coloring (AREA)
Description
Verfahren zum Reservieren von textilem Fasermaterial aus synthetischen Polyamiden
Gegenstand der Erfindung ist ein Verfahren zum Färben von textilem Fasermaterial aus synthetischen Polyamiden unter stellenweiser Reservierung gegen anionische Farbstoffe.
Es wurde gefunden, dass man wertvolle Färbungen bzw. Farbeffekte auf Fasermaterial aus synthetischen Polyamiden, das stellenweise gegen anionische (saure) Farbstoffe reserviert ist, erhält, wenn man es an den zur Reservierung vorgesehenen Stellen mit Imprägnier- flotten oder Druckpasten, die eine Lösung einer oder mehrerer farbloser, eine Dihalogentriazinylgruppe und eine oder mehrere Carbonsäure- oder Sulfonsäuregruppen als Substituenten tragender Verbindungen enthalten, imprägniert, die Imprägnierung fixiert und schliesslich das so reservierte Textilmaterial färbt.
Unter diesen farblosen, faserreaktiven Verbindungen sind insbesondere Verbindungen zu verstehen, in denen ein beliebiger, gegebenenfalls weitere Substituenten und/oder Heteroatome enthaltender, farbloser organischer Rest, der vorzugsweise bei 1000 C nicht merklich flüchtig sein soll, über eine Sauerstoff- oder Iminobrücke an den Dihalogentriazinylrest gebunden ist. Solche Verbindungen entsprechen zum Beispiel der Formel
EMI1.1
worin Hal Fluor, Chlor oder Brom, X eine Gruppe der Formel
EMI1.2
n 1, 2 oder 3 und R eine Alkylgruppe mit 1-4 Kohlenstoffatomen bedeuten, die -SO3H- und -COOH-Gruppen vorzugsweise nicht in ortho-Stellung zum Sauerstoffoder Imino-Brückenglied an den aromatischen Kern gebunden sind und die aromatischen Kerne z. B. Halogenatome, Nitro-, Cyan- oder Alkyl- oder Alkoxygruppen mit 1-4 Kohlenstoffatomen als weitere Substituenten tragen können.
Unter Fasermaterial aus synthetischen Polyamiden sind insbesondere Faservliese, Fäden, Gewebe oder Gewirke aus den verschiedenen Polyamid-Materialien, z. B. Nylon 6, Nylon 7, Nylon 10, Nylon 11, Nylon 66, Nylon 76, Nylon 226, Nylon 610 oder Nylon 6/66 zu verstehen.
Die Zubereitungen mit diesen Verbindungen werden vorzugsweise mit einem säurebindenden Mittel, z. B.
Alkalibicarbonat oder -carbonat, versetzt, damit der bei der Fixierung frei werdende Halogenwasserstoff sofort neutralisiert wird.
Beim Klotzen oder Bedrucken verwendet man meist die üblichen Verdickungsmittel, z. B. modifizierte oder nicht modifizierte natürliche Produkte, beispielsweise Alginate, Britischgummi, Gummi arabicum, Kristallgummi, Johannisbrotkernmehl, Tragant, Carboxyrnethylcellulose, Hydroxyäthylcellulose, Stärke oder synthetische Produkte, beispielsweise Polyacrylamide oder Polyvinylalkohole.
Die Druckpaste kann bis zu etwa 150 g der farblosen, faserreaktiven Verbindung im Kilogramm enthalten. Fixiert wird vorzugsweise in feuchter Atmosphäre bis zu etwa 20 Stunden bei Zimmertemperatur, bis 2 Stunden zwischen 25 und 950 C oder bis etwa 15 Minuten zwischen 95 und 1300. Die mit den farblosen, faserreaktiven Verbindungen behandelten Polyamidmaterialien können dann mit anionischen Farbstoffen gefärbt werden, wobei die zuvor mit den farblosen Verbindungen behandelten Stellen je nach Reservierungsgrad weniger bis überhaupt nicht angefärbt werden. Gegenüber anionischen Farbstoffen mit zwei oder mehr Sulfonsäuregruppen werden die besten Reservierungseffekte, nämlich bis zu 100 % Reservierung, erzielt. Stufenweise abnehmende Reservierung erzielt man beim Färben mit Farbstoffen, die nur 1 Sulfonsäuregruppe enthalten und Metallkomplexfarbstoffen.
Die Färbeeffekte mit Dispersionsfarbstoffen werden von diesen Reserviermitteln nicht beeinflusst, während die reservierten Stellen des Polyamidmaterials von basischen Farbstoffen in wesentlich tieferen Tönen gefärbt werden als die nicht reservierten Stellen. So können ausgezeichnete Bunteffekte erhalten werden, wenn man die reservierten Materialien nicht nur mit sauren, sondern gleichzeitig oder daran anschlie ssend auch mit (anders'farbigen) basischen Farbstoffen färbt. Das Färben erfolgt nach allgemein bekannten, praxisüblichen Bedingungen.
Aus der französischen Patentschrift Nr. 791 460 ist ein Verfahren zum Reservieren natürlicher Polyamidfasern bekannt, wobei das Fasermaterial zuerst in stark alkalischer, wässriger Lösung und sodann in einer organischen Lösung einer faserreaktiven Verbindung, gesprochen wird von Halogeniden organischer Säuren oder analogen Verbindungen, behandelt wird. Dieses Verfahren wird in zwei Bädern ausgeführt, es ist darum äusserst umständlich und für die stellenweise Reservierung praktisch ungeeignet. Ferner besteht die Gefahr, dass das Fasermaterial durch die Behandlung im stark alkalischen Bad geschädigt wird. Schliesslich treten bei diesem bekannten Verfahren grosse Verluste an faserreaktiver Verbindung durch Hydrolyse auf, wenn das feuchte Fasermaterial im zweiten Bad mit der faserreaktiven Verbindung in Kontakt gebracht wird.
So müssen, gemäss den Beispielen der französischen Pa tentschrift mindestens 50 %, bezogen auf das Gewicht des zu behandelnden Materials, an faserreaktiver Verbindung eingesetzt werden. Beim erfindungsgemässen Verfahren wird dagegen durch die Verwendung der genannten, schwächer alkalischen, säurebindenden Mittel eine Schädigung der Faser vermieden. Verluste an faserreaktiver Verbindung treten praktisch nicht auf; im allgemeinen werden, bezogen auf das Gewicht der reservierend behandelten Stellen, nur bis maximal 10 % an faserreaktiver Verbindung angewendet.
In der französischen Patentschrift Nr. 1 458 332 ist ein Verfahren zum Reservieren von Textilmaterialien aus synthetischen Polyamiden beschrieben. Zu diesem Zweck werden faserreaktive Verbindungen aus der 2,3-Dichlorchinoxalin- bzw. 1 ,4-Dichlorphthalazinreihe verwendet. Gegenüber diesen Verbindungen weisen die erfindungsgemäss verwendeten Reserviermittel zwei we sentliche Vorteile auf: 1. Die Halogentriazine, insbesondere das Cyanurchlorid, sind technisch leichter zugänglich, damit billiger, und 2. ist die Reaktionsfähigkeit der Halogentriazine allen anderen gebräuchlichen Reaktionssystemen überlegen.
Die grosse Reaktionsfähigkeit erlaubt es, die erfindungsgemäss verwendeten, Dihalogentriazinyl enthaltenden Verbindungen bei tieferer Temperatur auf der Faser zu fixieren als die aus der französischen Patentschrift Nr. 1 458 332 bekannten farblosen, faserreaktiven Verbindungen, anderseits ist der Zeitbedarf für die Fixierung der hier beanspruchten Verbindungen bei höheren Temperaturen wesentlich geringer als bei den bekannten, farblosen, faserreaktiven Verbindungen.
In den folgenden Beispielen bedeuten die Teile Gewichtsteile, die Temperaturen sind in Celsiusgraden angegeben.
Beispiel 1
Ein Nylon 6-Gewebe wurde im Vigoureuxdruck (Deckung 25 %, Gewichtszunahme der bedruckten Stellen 100 %) mit einer Druckpaste folgender Zusammen- Setzung imprägniert:
10 Teile Alginatverdickung,
30 Teile Dinatriumphosphat (wasserfrei),
2 Teile Mononatriumphosphat (wasserfrei), 921 Teile Wasser,
24 Teile Octylphenyl-pentaglykoläther,
6 Teile Lyogen CW (modifiziertes Na-alkylsulfat) und
7 Teile Natrium-2,4-dichlor-6-(phenylamino)- 1,3,5- triazin-4'-sulfonat.
Homogenität der Paste wurde durch intensives Rühren erreicht. Das imprägnierte Material wurde 24 Stunden bei Raumtemperatur (20-25 ) gelagert und anschliessend mit kaltem Wasser gespült. Das so behandelte Material wurde im Aufziehfärbeverfahren mit C.I.Acid Red 37 gefärbt. Die behandelten Stellen waren hellrot, die unbehandelten Stellen dunkelrot angefärbt.
Beispiel 2
Texturiertes Nylon 6-Garn wurde auf einen Wickelkörper gespult und stellenweise mit einer Imprägnierflotte folgender Zusammensetzung imprägniert (Ge wichtszunalune der imprägnierten Stellen 100 %):
1 Teil Alginatverdickung,
30 Teile Dinatriumphosphat (wasserfrei),
2 Teile Mononatriumphosphat (wasserfrei), 949 Teile Wasser,
8 Teile Octylphenyl-pentaglykoläther,
2 Teile Lyogen CW (modifiziertes Na-alkylsulfat) und
7 Teile Natrium-2,4-dichlor-6Xphenylamino)-1,3,5- triazin-4'-sulfonat.
Homogenität der Flotte wurde durch intensives Rühren erreicht. Das imprägnierte Material wurde
2 Stunden bei 400 gelagert und anschliessend mit war mem und kaltem Wasser gespült. Das so behandelte
Garn wurde anschliessend im Ausziehverfahren mit
C.I.Acid Red 37 und mit dem basischen Farbstoff der
Formel
EMI3.1
unter Zusatz einer Mischung aus Oleyl-decaglykol ätheroxyessigsäure und dem Kondensationsprodukt aus 3-Stearyloxy-3-hydroxypropyl-diäthylentriamin und 10 Äthylenoxidgruppen, wie üblich gefärbt. Die imprä gnierten Stellen waren stark blau, die unbehandelten Stellen stark rot gefärbt.
Beispiel 3
Nylon-6-Garn wurde mit einer Imprägnierflotte folgender Zusammensetzung stellenweise imprägniert (Gewichtszunahme an den behandelten Stellen 100 %):
5 Teile Alginatverdickung,
30 Teile Dinatriumphosphat (wasserfrei),
2 Teile Mononatriumphosphat (wasserfrei), 944 Teile Wasser,
8 Teile Octylphenyl-pentaglykoläther,
2 Teile Lyogen CW (modifiziertes Na-alkylsulfat) und
7 Teile Natrium-2,4-dichlor-6-(phenylamino)-1,3,5- triazin-4'-sulfonat.
Homogenität der Imprägnierflotte wurde durch in tensives Rühren erreicht. Das Material wurde 4 Minuten bei 1020 behandelt und anschliessend mit kaltem Wasser gespült. Das so behandelte Garn wurde verwoben und das Gewebe im Ausziehfärbeverfahren mit einem basi schen Blau folgender Formel gefärbt.
EMI3.2
Auf diese Weise wurde eine Ton-in-Tonfärbung erreicht.
Die folgende Tabelle enthält weitere Beispiele von Färbungen mit stellenweiser Reservierung. Diese Färbungen wurden nach den Angaben in den vorherigen Beispielen ausgeführt und sind in der Tabelle durch das verwendete Material und durch die Substituenten Hal und X im Reservierungsmittel der Formel
EMI3.3
gekennzeichnet.
Ausführung Bsp. Nr. Textilmaterial Hal Substituent X nach
Beispiel
5 Nyon-6 C1 3-Sulfophenylamino 2
6 do. C1 4-Carboxyphenoxy 2
7 Nylon 11 C1 3-Sulfophenylamino 1
8 Nylon 66 C1 4-Sulfonaphthyl-1 -amino 2
9 do. C1 6-Sulfonaphthoxy-2 2
10 do. C1 6,8-Disulfonaphthoxy-2- 2
11 do. C1 4-Sulfophenoxy 2
12 Nylon 6 C1 2,5-Disulfophenylamino 1
13 Nylon 66 C1 2,4-Disulfophenylamino 1
14 Nylon 6 C1 4-Sulfonaphthoxy-1 2
15 do. C1 4,6-Msulfonaphthoxy-1 2
16 do. C1 7-Sulfonaphthyl-l-amino 1
17 do. C1
4,8-Disulfonaphthyl-2-amino 1
18 Nylon 6 C1 5,7-Disulfonaphthyl-1-amino 1
19 Nylon 6/66 C1 6-Sulfonaphthyl-2-amino 1
20 Nylon 6 C1 N-Methyl-N-(6-sulfonaphthyl-2)-amino 3
21 Nylon 66 C1 N-Methyl-N-(4-sulfophenyl)-annno 3
22 Nylon 6 Br 4-Sulfophenylamino 2
23 do. C1 4,6,8-Trisulfonaphthyl-2-amino 1
24 do. C1 3,6,8-Trisulfonaphthyl-l-amino 1
25 do. Cl 3,6,8-Trisulfonaphthoxy-1 1
26 Nylon 66 C1 3,5-Disulfophenylamino 2
27 Nylon 6 F 4-Sulfophenylamino 2
Method for reserving textile fiber material made from synthetic polyamides
The invention relates to a process for dyeing textile fiber material made from synthetic polyamides with a local reservation against anionic dyes.
It has been found that valuable dyeings or color effects on fiber material made of synthetic polyamides, which is reserved in places against anionic (acidic) dyes, are obtained if it is used in the areas intended for reservation with impregnation liquors or printing pastes that contain a solution of a or contain more than one colorless, one dihalotriazinyl group and one or more carboxylic acid or sulfonic acid groups as compounds bearing substituents, impregnate, fix the impregnation and finally dye the reserved textile material.
These colorless, fiber-reactive compounds are to be understood as meaning, in particular, compounds in which any colorless organic radical, optionally containing further substituents and / or heteroatoms, which should preferably not be noticeably volatile at 1000 ° C., via an oxygen or imino bridge to the dihalotriazinyl radical is bound. Such compounds correspond, for example, to the formula
EMI1.1
wherein Hal is fluorine, chlorine or bromine, X is a group of the formula
EMI1.2
n is 1, 2 or 3 and R is an alkyl group with 1-4 carbon atoms, the -SO3H- and -COOH groups are preferably not attached to the aromatic nucleus in the ortho position to the oxygen or imino bridge member and the aromatic nuclei are e.g. B. halogen atoms, nitro, cyano or alkyl or alkoxy groups with 1-4 carbon atoms as further substituents.
Fiber material made from synthetic polyamides includes, in particular, nonwovens, threads, woven fabrics or knitted fabrics made from various polyamide materials, e.g. Nylon 6, nylon 7, nylon 10, nylon 11, nylon 66, nylon 76, nylon 226, nylon 610 or nylon 6/66.
The preparations with these compounds are preferably treated with an acid-binding agent, e.g. B.
Alkali bicarbonate or carbonate, added so that the hydrogen halide released during fixation is immediately neutralized.
When padding or printing, the usual thickeners are usually used, e.g. B. modified or unmodified natural products, such as alginates, British gum, gum arabic, crystal gum, locust bean gum, tragacanth, carboxymethyl cellulose, hydroxyethyl cellulose, starch or synthetic products such as polyacrylamides or polyvinyl alcohols.
The printing paste can contain up to about 150 g of the colorless, fiber-reactive compound per kilogram. Fixing is preferably carried out in a humid atmosphere for up to about 20 hours at room temperature, up to 2 hours between 25 and 950 C or up to about 15 minutes between 95 and 1300. The polyamide materials treated with the colorless, fiber-reactive compounds can then be dyed with anionic dyes, whereby the areas previously treated with the colorless compounds are colored less or not at all, depending on the degree of reservation. Compared to anionic dyes with two or more sulfonic acid groups, the best reservation effects, namely up to 100% reservation, are achieved. Gradually decreasing reservation is achieved when dyeing with dyes that contain only 1 sulfonic acid group and metal complex dyes.
The coloring effects with disperse dyes are not influenced by these reservation agents, while the reserved areas of the polyamide material are colored by basic dyes in much deeper shades than the unreserved areas. Excellent colorful effects can be obtained if the reserved materials are not only colored with acidic, but at the same time or afterwards with (differently colored) basic dyes. The dyeing is carried out according to generally known, customary conditions.
A method for reserving natural polyamide fibers is known from French patent specification No. 791 460, the fiber material being treated first in a strongly alkaline, aqueous solution and then in an organic solution of a fiber-reactive compound, spoken of halides of organic acids or analogous compounds. This procedure is carried out in two bathrooms, which is why it is extremely cumbersome and practically unsuitable for making reservations in places. There is also the risk that the fiber material will be damaged by the treatment in the strongly alkaline bath. Finally, in this known method, large losses of fiber-reactive compound occur due to hydrolysis when the moist fiber material is brought into contact with the fiber-reactive compound in the second bath.
According to the examples of the French patent, at least 50%, based on the weight of the material to be treated, of fiber-reactive compound must be used. In the process according to the invention, on the other hand, damage to the fiber is avoided by using the weaker alkaline acid-binding agents mentioned. There are practically no losses of fiber-reactive compound; In general, only up to a maximum of 10% of fiber-reactive compound are used, based on the weight of the areas treated with reserve.
In French patent specification No. 1,458,332 a method for reserving textile materials made from synthetic polyamides is described. For this purpose, fiber-reactive compounds from the 2,3-dichloroquinoxaline or 1,4-dichlorophthalazine series are used. The reservation agents used according to the invention have two major advantages over these compounds: 1. The halotriazines, in particular cyanuric chloride, are technically more easily accessible and therefore cheaper, and 2. the reactivity of the halotriazines is superior to all other common reaction systems.
The high reactivity allows the dihalotriazinyl-containing compounds used according to the invention to be fixed on the fiber at a lower temperature than the colorless, fiber-reactive compounds known from French Patent No. 1,458,332; on the other hand, the time required for fixing the compounds claimed here is higher temperatures significantly lower than with the known, colorless, fiber-reactive compounds.
In the following examples, the parts are parts by weight and the temperatures are given in degrees Celsius.
example 1
A nylon 6 fabric was impregnated in vigoureux printing (coverage 25%, weight increase of the printed areas 100%) with a printing paste of the following composition:
10 parts alginate thickener,
30 parts disodium phosphate (anhydrous),
2 parts monosodium phosphate (anhydrous), 921 parts water,
24 parts of octylphenyl pentaglycol ether,
6 parts Lyogen CW (modified Na-alkyl sulfate) and
7 parts of sodium 2,4-dichloro-6- (phenylamino) -1,3,5-triazine-4'-sulfonate.
The homogeneity of the paste was achieved by vigorous stirring. The impregnated material was stored for 24 hours at room temperature (20-25) and then rinsed with cold water. The material treated in this way was stained with C.I.Acid Red 37 using the mounting dyeing process. The treated areas were light red, the untreated areas were colored dark red.
Example 2
Textured nylon 6 yarn was wound onto a bobbin and impregnated in places with an impregnation liquor of the following composition (total weight of the impregnated areas 100%):
1 part alginate thickener,
30 parts disodium phosphate (anhydrous),
2 parts monosodium phosphate (anhydrous), 949 parts water,
8 parts of octylphenyl pentaglycol ether,
2 parts Lyogen CW (modified Na-alkyl sulfate) and
7 parts of sodium 2,4-dichloro-6Xphenylamino) -1,3,5-triazine-4'-sulfonate.
The liquor was homogenized by vigorous stirring. The impregnated material was
Stored for 2 hours at 400 and then rinsed with war mem and cold water. Treated like that
Yarn was then used in the exhaust process
C.I.Acid Red 37 and with the basic dye der
formula
EMI3.1
with the addition of a mixture of oleyl decaglycol etheroxyacetic acid and the condensation product of 3-stearyloxy-3-hydroxypropyl-diethylenetriamine and 10 ethylene oxide groups, colored as usual. The impregnated areas were colored strongly blue, the untreated areas strongly red.
Example 3
Nylon 6 yarn was impregnated in places with an impregnation liquor of the following composition (weight increase at the treated areas 100%):
5 parts alginate thickener,
30 parts disodium phosphate (anhydrous),
2 parts monosodium phosphate (anhydrous), 944 parts water,
8 parts of octylphenyl pentaglycol ether,
2 parts Lyogen CW (modified Na-alkyl sulfate) and
7 parts of sodium 2,4-dichloro-6- (phenylamino) -1,3,5-triazine-4'-sulfonate.
The impregnation liquor was homogeneous by vigorous stirring. The material was treated for 4 minutes at 1020 and then rinsed with cold water. The yarn treated in this way was woven and the fabric was dyed in the exhaust dyeing process with a basic blue of the following formula.
EMI3.2
In this way a tone-on-tone coloration was achieved.
The following table contains further examples of staining with local reservation. These colorations were carried out as described in the previous examples and are indicated in the table by the material used and by the substituents Hal and X in the reservation agent of the formula
EMI3.3
marked.
Execution example no. Textile material Hal substituent X after
example
5 Nyon-6 C1 3-sulfophenylamino 2
6 do. C1 4-carboxyphenoxy 2
7 nylon 11 C1 3-sulfophenylamino 1
8 nylon 66 C1 4-sulfonaphthyl-1 -amino 2
9 do. C1 6-sulfonaphthoxy-2 2
10 do. C1 6,8-disulfonaphthoxy-2-2
11 do. C1 4-sulfophenoxy 2
12 nylon 6 C1 2,5-disulfophenylamino 1
13 nylon 66 C1 2,4-disulfophenylamino 1
14 nylon 6 C1 4 sulfonaphthoxy-12
15 do. C1 4,6-msulfonaphthoxy-12
16 do. C1 7-sulfonaphthyl-1-amino 1
17 th. C1
4,8-disulfonaphthyl-2-amino 1
18 nylon 6 C1 5,7-disulfonaphthyl-1-amino 1
19 nylon 6/66 C1 6-sulfonaphthyl-2-amino 1
20 nylon 6 C1 N-methyl-N- (6-sulfonaphthyl-2) -amino 3
21 nylon 66 C1 N-methyl-N- (4-sulfophenyl) -annno 3
22 nylon 6 Br 4 sulfophenylamino 2
23 do. C1 4,6,8-trisulfonaphthyl-2-amino 1
24 th. C1 3,6,8-trisulfonaphthyl-1-amino 1
25 do. Cl 3,6,8-trisulfonaphthoxy-11
26 nylon 66 C1 3,5-disulfophenylamino 2
27 nylon 6 F 4-sulfophenylamino 2
Claims (1)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH942967D CH942967A4 (en) | 1967-07-03 | 1967-07-03 | |
| CH942967A CH525997A (en) | 1967-07-03 | 1967-07-03 | Method for reserving textile fiber material made from synthetic polyamides |
| US00739214A US3743477A (en) | 1967-07-03 | 1968-06-24 | Process for reserving textiles of natural polyamide fibres and of synthetic fibres dyeable with acid dyes |
| GB1226653D GB1226653A (en) | 1967-07-03 | 1968-06-25 | |
| BE717378D BE717378A (en) | 1967-07-03 | 1968-06-28 | |
| DE19681769702 DE1769702B (en) | 1968-07-01 | Process for reserving fiber material made from natural polyamides or synthetic materials which can be dyed with acidic dyes | |
| NL6809336A NL144689B (en) | 1967-07-03 | 1968-07-02 | METHOD OF DYEING FIBER MATERIALS BY FIRST RESERVING LOCAL WITH 2,4-DIHALOGEN-6-AMINO-1,3,5-TRIAZINES, AND THEN DYEING. |
| FR1573425D FR1573425A (en) | 1967-07-03 | 1968-07-02 | |
| MY7400196A MY7400196A (en) | 1967-07-03 | 1974-12-30 | Process for reserving textiles of natural polyamide fibres and of synthetic fibres dyeable with acid dyes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH942967A CH525997A (en) | 1967-07-03 | 1967-07-03 | Method for reserving textile fiber material made from synthetic polyamides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH525997A true CH525997A (en) | 1972-03-30 |
Family
ID=4351883
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH942967A CH525997A (en) | 1967-07-03 | 1967-07-03 | Method for reserving textile fiber material made from synthetic polyamides |
| CH942967D CH942967A4 (en) | 1967-07-03 | 1967-07-03 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH942967D CH942967A4 (en) | 1967-07-03 | 1967-07-03 |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US3743477A (en) |
| CH (2) | CH525997A (en) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2244060B2 (en) * | 1972-09-08 | 1974-10-03 | Farbwerke Hoechst Ag, Vormals Meister Lucius & Bruening, 6000 Frankfurt | Process for evenly dyeing wool that has been made felt-free with polyimine or polyamine resin |
| US4083682A (en) * | 1974-03-14 | 1978-04-11 | Rohm And Haas Company | Method for producing variegated nylon yarn |
| US4218217A (en) * | 1974-04-01 | 1980-08-19 | Sandoz, Inc. | Method of producing multicolor dyeings |
| DE2641159A1 (en) * | 1975-09-23 | 1977-03-31 | Sandoz Ag | METHOD OF COLORING AND PRINTING TEXTILES |
| US4106896A (en) * | 1977-02-07 | 1978-08-15 | Champion International Corporation | Method for producing multicolor printed web material |
| US4087243A (en) * | 1977-02-22 | 1978-05-02 | Milliken Research Corporation | Polymer-printed fabric and method for producing same |
| US4131422A (en) * | 1977-02-22 | 1978-12-26 | Milliken Research Corporation | Polymer-printed fabric and method for producing same |
| DE2828030A1 (en) * | 1977-07-07 | 1979-01-25 | Sandoz Ag | COLORING PROCESS |
| US4410330A (en) * | 1977-08-19 | 1983-10-18 | Sandoz, Ltd. | Method of producing multi-colored dyeings |
| US4222740A (en) * | 1979-03-05 | 1980-09-16 | Armstrong Cork Company | Coloration method for textiles |
| US4321808A (en) * | 1980-04-16 | 1982-03-30 | Glen Head Inc. | Apparatus for treatment of yarn in package form |
| US4343923A (en) * | 1980-08-07 | 1982-08-10 | Armstrong World Industries, Inc. | Process for reducing the acid dye uptake of polyamide textile materials with N-acylimidazole compound |
| US4313732A (en) * | 1980-10-30 | 1982-02-02 | Burlington Industries, Inc. | Process for improving washfastness of indigo-dyed fabrics |
| EP0302013A1 (en) * | 1987-07-27 | 1989-02-01 | Ciba-Geigy Ag | Process for dyeing polyamide textile fabrics |
| US5571444A (en) * | 1989-09-11 | 1996-11-05 | Invicta Group Industries Pty Ltd. | Textile treatment |
| US20020124323A1 (en) * | 2001-01-09 | 2002-09-12 | Cliver James D. | Process for patterning textile materials and fabrics made therefrom |
| US20050144738A1 (en) * | 2003-12-29 | 2005-07-07 | Shin-Chang Wu | Method for double color dyeing |
| US9718944B2 (en) | 2015-04-02 | 2017-08-01 | Cnh Industrial Canada, Ltd. | Method of coloring biocomposite materials |
| US20190053653A1 (en) * | 2017-08-17 | 2019-02-21 | The Boeing Company | Light transmissive carpet for vehicle |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR576725A (en) * | 1923-01-09 | 1924-08-25 | Ste Ind Chim Bale | New azo dyestuffs and processes for their manufacture |
| GB842415A (en) * | 1956-11-21 | 1960-07-27 | Ici Ltd | New textile coloration process |
| BE600676A (en) * | 1960-03-01 | 1900-01-01 | ||
| DE1155088B (en) * | 1960-11-02 | 1963-10-03 | Basf Ag | Process for coloring, printing and / or optical brightening of textile goods |
| BE636485A (en) * | 1962-08-22 |
-
1967
- 1967-07-03 CH CH942967A patent/CH525997A/en not_active IP Right Cessation
- 1967-07-03 CH CH942967D patent/CH942967A4/xx unknown
-
1968
- 1968-06-24 US US00739214A patent/US3743477A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CH942967A4 (en) | 1972-03-30 |
| US3743477A (en) | 1973-07-03 |
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| PL | Patent ceased |