CH422711A - Process for improving the dyeability of textile cellulose fibers - Google Patents
Process for improving the dyeability of textile cellulose fibersInfo
- Publication number
- CH422711A CH422711A CH1450164A CH1450164A CH422711A CH 422711 A CH422711 A CH 422711A CH 1450164 A CH1450164 A CH 1450164A CH 1450164 A CH1450164 A CH 1450164A CH 422711 A CH422711 A CH 422711A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- solution
- sultone
- fibers
- cellulose fibers
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 24
- 229920003043 Cellulose fiber Polymers 0.000 title claims description 12
- 239000004753 textile Substances 0.000 title claims description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 42
- 239000000243 solution Substances 0.000 claims description 30
- 239000003513 alkali Substances 0.000 claims description 16
- 239000000835 fiber Substances 0.000 claims description 11
- 150000008053 sultones Chemical class 0.000 claims description 10
- -1 hydrocarbon sultone Chemical class 0.000 claims description 9
- FSSPGSAQUIYDCN-UHFFFAOYSA-N 1,3-Propane sultone Chemical group O=S1(=O)CCCO1 FSSPGSAQUIYDCN-UHFFFAOYSA-N 0.000 claims description 8
- 239000004215 Carbon black (E152) Substances 0.000 claims description 6
- 229920002678 cellulose Polymers 0.000 claims description 6
- 239000001913 cellulose Substances 0.000 claims description 6
- 229930195733 hydrocarbon Natural products 0.000 claims description 6
- 239000000080 wetting agent Substances 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000002657 fibrous material Substances 0.000 description 5
- 229920000742 Cotton Polymers 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
- 241000219146 Gossypium Species 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 229920000297 Rayon Polymers 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 238000005470 impregnation Methods 0.000 description 3
- 238000005517 mercerization Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000001294 propane Substances 0.000 description 3
- 229920002994 synthetic fiber Polymers 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- XZIIFPSPUDAGJM-UHFFFAOYSA-N 6-chloro-2-n,2-n-diethylpyrimidine-2,4-diamine Chemical compound CCN(CC)C1=NC(N)=CC(Cl)=N1 XZIIFPSPUDAGJM-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- 229920000615 alginic acid Polymers 0.000 description 2
- 235000010443 alginic acid Nutrition 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 229920002301 cellulose acetate Polymers 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 238000007598 dipping method Methods 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- CXKWCBBOMKCUKX-UHFFFAOYSA-M methylene blue Chemical compound [Cl-].C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 CXKWCBBOMKCUKX-UHFFFAOYSA-M 0.000 description 2
- 229960000907 methylthioninium chloride Drugs 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000002964 rayon Substances 0.000 description 2
- 229940035044 sorbitan monolaurate Drugs 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- FCYVWWWTHPPJII-UHFFFAOYSA-N 2-methylidenepropanedinitrile Chemical compound N#CC(=C)C#N FCYVWWWTHPPJII-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 229920002972 Acrylic fiber Polymers 0.000 description 1
- 241001226611 Allium textile Species 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 229920002466 Dynel Polymers 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 244000299507 Gossypium hirsutum Species 0.000 description 1
- 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 1
- VAYOSLLFUXYJDT-RDTXWAMCSA-N Lysergic acid diethylamide Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N(CC)CC)C2)=C3C2=CNC3=C1 VAYOSLLFUXYJDT-RDTXWAMCSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229940072056 alginate Drugs 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229940088990 ammonium stearate Drugs 0.000 description 1
- 159000000032 aromatic acids Chemical class 0.000 description 1
- JPNZKPRONVOMLL-UHFFFAOYSA-N azane;octadecanoic acid Chemical compound [NH4+].CCCCCCCCCCCCCCCCCC([O-])=O JPNZKPRONVOMLL-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000000981 basic dye Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229940106691 bisphenol a Drugs 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- QKSIFUGZHOUETI-UHFFFAOYSA-N copper;azane Chemical compound N.N.N.N.[Cu+2] QKSIFUGZHOUETI-UHFFFAOYSA-N 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- TWFQJFPTTMIETC-UHFFFAOYSA-N dodecan-1-amine;hydron;chloride Chemical compound [Cl-].CCCCCCCCCCCC[NH3+] TWFQJFPTTMIETC-UHFFFAOYSA-N 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- 239000011152 fibreglass Substances 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- RNYJXPUAFDFIQJ-UHFFFAOYSA-N hydron;octadecan-1-amine;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[NH3+] RNYJXPUAFDFIQJ-UHFFFAOYSA-N 0.000 description 1
- 125000003010 ionic group Chemical group 0.000 description 1
- 229940070765 laurate Drugs 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 239000002557 mineral fiber Substances 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229960003975 potassium Drugs 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229940045845 sodium myristate Drugs 0.000 description 1
- JUQGWKYSEXPRGL-UHFFFAOYSA-M sodium;tetradecanoate Chemical compound [Na+].CCCCCCCCCCCCCC([O-])=O JUQGWKYSEXPRGL-UHFFFAOYSA-M 0.000 description 1
- 229940114926 stearate Drugs 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- GINSRDSEEGBTJO-UHFFFAOYSA-N thietane 1-oxide Chemical compound O=S1CCC1 GINSRDSEEGBTJO-UHFFFAOYSA-N 0.000 description 1
- 210000002268 wool Anatomy 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
- D06P1/65168—Sulfur-containing compounds
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M11/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising
- D06M11/32—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with oxygen, ozone, ozonides, oxides, hydroxides or percompounds; Salts derived from anions with an amphoteric element-oxygen bond
- D06M11/36—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with oxygen, ozone, ozonides, oxides, hydroxides or percompounds; Salts derived from anions with an amphoteric element-oxygen bond with oxides, hydroxides or mixed oxides; with salts derived from anions with an amphoteric element-oxygen bond
- D06M11/44—Oxides or hydroxides of elements of Groups 2 or 12 of the Periodic Table; Zincates; Cadmates
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
- D06M13/224—Esters of carboxylic acids; Esters of carbonic acid
- D06M13/228—Cyclic esters, e.g. lactones
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/244—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus
- D06M13/248—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus with compounds containing sulfur
- D06M13/256—Sulfonated compounds esters thereof, e.g. sultones
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/39—Aldehyde resins; Ketone resins; Polyacetals
- D06M15/423—Amino-aldehyde resins
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/39—Aldehyde resins; Ketone resins; Polyacetals
- D06M15/423—Amino-aldehyde resins
- D06M15/429—Amino-aldehyde resins modified by compounds containing sulfur
-
- 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
- D06P5/22—Effecting variation of dye affinity on textile material by chemical means that react with the fibre
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Chemical Or Physical Treatment Of Fibers (AREA)
Description
Verfahren zur Verbesserung der Anfärbbaxkeit von textilen Cellulosefasern Die Erfindung betrifft ein Verfahren zur Verbes- serung der Anfärbbarkeit von textilen Cellulose- fasern, welches dadurch gekennzeichnet ist,
dass man die Cellulosefasern zuerst mit einer wässrigen Alkali- fösung und dann mit einer Lösung behandelt, die einen Kohlenwasserstoffsulton enthält.
Es ist bereits bekannt, Natriumcellulose mit Kohlenwasserstoffsultonen zu behandeln. Man erhält dabei eine weisse leichte Masse mit Faserstruktur, welche in Wasser leicht löslich ist.
Deshalb war es überraschend, dass mit dem erfindungsgemässen Ver fahren textile Cellulosefasern erhalten werden kön nen, deren Anfärbbarkeit gegenüber unbehandelten Fasern oder nur mit Natronlauge behandelten Fa sern ganz erheblich besser ist, ohne dass die Fasern ihre sonstigen textilen Eigenschaften merklich ein büssen.
Das erfindungsgemässe Verfahren kann zur Be- handlung von textilen Cellulosefasern jeder Art an gewendet werden. Diese Fasern können als gewebte und nicht gewebte Waren, Fäden, Gaze, Garn, Cord samt, Bindfaden, Netzwerk und dergleichen vorliegen. Das Verfahren schliesst auch die Behandlung von textilen Cellulosefasem ein, die bereits vorbehandelt, z. B. merverisiert wurden.
Man kann erfindungsge mäss Fasern behandeln, die einen beliebigen, vor zugsweise mindestens 30prozentigen Anteil an Cellu- losestoffen, wie natürliche Cellulose, z. B. Baum wolle oder Leinen, oder andere Cellulosestoffe, wie Viskose- oder Kupferammoniak-Reyon, Regenerat- cellulbse oder Celluloseacetat enthalten. Gegebenen falls können die Cellulosefasern im Gemisch mit Wolle und Kunstfasern vorliegen, z.
B. mit Fasern aus Acrylnitril ( Orlon , ein 100%iges Acrylnitril polymer) oder aus Vinylidencyanidpolymeren oder Polyamiden {Nylon, aus Polyester-Polyamiden, aus Polymerisaten von Maisprotein und Formaldehyd, oder aus Copolymeris'aten der oben genannten Mo nomeren, wie z.
B. Acrilan (85% Acrylnitril und <B>15%</B> Vinylacetat), Dynel (60% Vinylchlorid und 40 % Acrylnitril), Saran (85 % Vinylidenchlorid und 15 Vinylehlorid). Auch andere synthetische Stoffe oder Fasern, hergestellt aus Polyalkylenen, wie Poly äthylen oder Polypropylen, Polyurthanen,
Mineral- fasern (Fiberglas) oder Alginsäurestoffen, wie Algi- natreyon kommen als Zusatz zu den Cellulosefasern in Frage.
Bevorzugt zur Verwendung bei dem Verfahren nach der Erfindung sind u. a. Textilfasern mit einem mindestens 60-prozentigen Celluloseanteil, der ins besondere aus Baumwolle, Reyon und Celluloseacetat bestehen kann.
Es wurde gefunden, dass durch Anwendung des Verfahrens nach der Erfindung das cellulosehaltige Fasermaterial derart modifiziert werden kann, dass es eine stark erhöhte Reaktionsfähigkeit gegenüber an deren Stoffen, wie etwa basischen Farbstoffen, auf weist. Mit diesen reagieren die .erfindungsgemäss behandelten Fasern ohne weiteres und die erhaltenen Färbungen sind tiefer und widerstandsfähiger gegen das Ausbleichen bei Belichtung und Waschen.
Bei Durchführung des Verfahrens nach der Er findung wird das zu behandelnde Cellulosefasermate- rial mit einer wässrigen Alkalilösung in Berührung ge bracht, und zwar vorzugsweise mit einer Natrium hydroxydlösung, die jedoch auch durch eine Kalium hydroxyd- oder eine andere Alkali- oder Erdalkali hydroxydlösung ersetzt sein kann. Die Stärke der Älkalilösung kann weitgehend verschieden sein;
be- vorzogt sind Konzentrationen zwischen 1 und 30, insbesondere von 5 bis 20 Gew. %. Bei den üblichen Mercerisierungsverfahren werden Alkalilösungen in einer Konzentration von 16 bis 18 % verwendet, die sich auch für das Verfahren nach der Erfindung in idealer Weise eignen.
Praktisch kann sich die zweite Stufe des Verfahrens unmittelbar an die Mercerisierungsstufe anschliessen und fügt sich daher in die normale Nassbehandlung von Textilien ein.
Das Imprägnieren oder Tränken mit dem wäss- rigen Alkali kann auf beliebige Weise erfolgen, z. B. durch Tauchen, Besprühen oder Klotzen. Vorzugs weise zieh man, wie bei der bekannten Klotztechnik, das Material durch die wüssrige Lösung hindurch. Die aufgenommene Nassmenge schwankt je nach dem betreffenden Fall; sie beträgt vorzugsweise 20 bis, 100 Teile Lösung je 100 Teile trockenes Material.
Die Temperatur der Alkalilösung und diejenige des zu tränkenden Materials. kann verschieden sein; vorzugsweise entsprechen beide etwa der Raumtem peratur. Mercerisierungstemperaturen zwischen 10 und 40 C sind im allgemeinen bevorzugt.
Anschliessend wird mit der Al'kalilösung getränkte Material mit einer Lösung eines Sultons behandelt.
Die erfindungsgemäss zu verwendenden Sultone sind intermolekulare cyclische Ester von Hydroxy- sulfonsäuren und können von aliphabischen, cyclo- aliphatischen oder aromatischen Säuren abgeleitet sein.
Beispie'l'e für erfindungsgemäss brauchbare Sul tone sind die 1,3-Propansultone, die 1,4 Butansul- tone, die 1,3-Hexansultone und die Benzyl- und Toluysultone, sowie Gemische daraus..
Die zu ver wendenden Sultone können die Gammasultone sein wie das 1,3-Propansukon. Die Sultone können auf übliche Weise hergestellt werden, z.
B. durch Sulfo- chlorierung von chlorierten Kohlenwasserstoffen, wo bei man die entstandene Chlorsulfonsäure dann für die Bildung der Sultone benützt. Die Sultonlösun- gen können auf beliebige Weise bereitet werden, z.
B. durch Vermischen des Sultons mit Wasser, Aceton oder Alkohol oder Gemischen daraus. Im allgemeinen verwendet man vorzugsweise eine wäss- rige Lösung.
Die Konzentration der Sultonlösungen kann innerhalb eines weiten Bereiches variiert wer den; bevorzugt ist die Verwendung von Lösungen mit einem Gehalt an 1 bis 25 Gewichtsprozent Sulton.
Gegebenenfalls kann es von Vorteil sein, Netzmit tel zuzusetzen, wozu eine grössere Anzahl verschie dener Verbindungen von kationischem, anionischem oder nichtionischem Charakter zur Verfügung ste- hen. Bevorzugt sind die ionischen Mittel und insbe sondere diejenigen mit polarer Struktur,
bei denen an einen hydrophilen (vorwiegend Kohlenwasser- stoff-)Rest eine geladene ionische Gruppe gebunden ist.
Solche aniönische oberflächenaktive Verbindun- gen sind u. a. die Alkali- und Ammoniumseifen höhe rer Fettsäuren, wie Kalium- oder Natriummyristat, -laurat, -palmitat, -oleat oder -stearat oder Ammo- niumstearat;
auch die Salze langkettiger aliphati scher Amine und quaternärer Ammoniumbasen, wie Laurylaminhydrochlorid und Stearylaminhydrochlorid sind geeignet. Beispiele für nichtionische Mittel sind u. a. die Teilester von mehrwertigen Alkoholen und Fettsäuren, wie die Hexitane und Hexitidester, z. B.
Sorbitanmonolaurat, die Hydroxypolyoxyalkylenäther der oben genannten Teilester z. B. die Polyäthylen- glykoläther des Sorbitanmonolaurates, oder die Hy- droxypolyoxyalkylenäther von Phenolen, wie das Reaktionsprodukt aus Athylenoxyd und Bisphenol-A oder Gemische aus den genannten Substanzen.
Die Netzmittel werden vorzugsweise in Mengen von 0,1 bis 5 Gew. %, insbesondere von 0,5 bis 3 Gew. % zugesetzt.
Das Tränken des mit Alkali vorbehandelten Fasermaterials kann auf beliebige Weise erfolgen, z. B. durch Tauchen, Besprühen oder Klotzen. Im allgemeinen ist es zweckmässig, das Fasermaterial durch die Sultoulösung hindurchzuziehen, wie dies beim Klotzen geschieht. Die Menge an aufgenom mener Lösung kann je nach den Umständen ver schieden sein, liegt jedoch vorzugsweise zwischen 10 und<B>100%.</B>
Die Temperatur der Sultonlösung sowie diejenige des zu tränkenden, alkalisch vorbehandelten Faser materials, kann in weiten Grenzen, z. B. zwischen 15 und 90 C schwanken und liegt vorzugsweise zwischen 20 und 70 C.
Die für die Reaktion mit dem Sulton notwendige Zeit hängt von der Temperatur und der Konzentra tion der Lösung ab. Bei erhöhter Temperatur ist die Umsetzung in den meisten Fällen innerhalb einer oder zwei Stunden vollständig.
Nach dem Herausnehmen des imprägnierten Materials aus der Sultonlösung wird es zur Entfer nung der noch anhaftenden Reaktionsteilnehmer ge waschen, getrocknet und ist dann unmittelbar für die Färbung bereit. Das Waschen erfolgt vorzugsweise mit Wasser, dem gegebenenfalls, Reinigungsmittel (Detergentien) zugesetzt werden können. Das Trock nen erfolgt zweckmässig bei Temperaturen zwischen Raumtemperatur und 125 C.
Beispiel <I>1</I> Ein Baumwollstoff wurde 15 Minuten bei 24 C mit 20 % iger Natronlauge und anschliessend 60 Minuten bei 49 C mit einer 10 % igen Propansul- tonlösung behandelt.
Baumwollstoffmuster von 7,5X7,5 cm wurden dann eingefärbt durch halb ständiges Kochen mit 0,1 % Methyl'enblau und 0,1 Essigsäure. Die Reflexion in Prozent wurde bestimmt; sie ist in. der Tabelle angegeben im Vergleich mit derjenigen der unbehandelten Ware und der ledig lich mit Alkali behandelten Ware.
Es wurden fol gende Resultate erhalten:
EMI0003.0001
Reflexion
<tb> Ware <SEP> Farbe <SEP> in
<tb> unbehandelt <SEP> königsblau <SEP> 44
<tb> nur <SEP> mit <SEP> 20%iger <SEP> NaOH <SEP> dunkleres <SEP> Blau
<tb> behandelt <SEP> als <SEP> oben
<tb> behandelt <SEP> mit <SEP> 20%iger <SEP> sehr <SEP> dunkles <SEP> Blau
<tb> NaOH, <SEP> nachbehandelt
<tb> mit <SEP> 10%igem <SEP> Propan sulton <I>Beispiel 2</I> In weiteren Versuchsreihen wurde die verbesserte Farbaufnahmefähigkeit von behandelten Baumwoll- fasern gezeigt,
wobei ein weniger konzentriertes Farbband und verschiedene Mengen an Propansul- ton benutzt wurden. Die Stoffmuster von 7,5X7,5 cm wurden 30 Minuten in 0,01 % igem Methylenblau mit 0,01 % Essigsäure gekocht. Die Resultate gehen aus der Tabelle hervor.
EMI0003.0015
Behandlung, <SEP> Min/cl <SEP> C <SEP> Farbe <SEP> Reflexion
<tb> in
<tb> unbehandelt <SEP> hellblau <SEP> 69
<tb> 20% <SEP> NaOH, <SEP> 60/49 <SEP> hellblau <SEP> 69
<tb> 20% <SEP> NaOH, <SEP> 60/49 <SEP> dunkelblau <SEP> 20 25% <SEP> Propansulton, <SEP> 90/24
<tb> 20% <SEP> NaOH, <SEP> 15/24 <SEP> dunkelblau <SEP> 19
<tb> <B>10%</B> <SEP> Propansulton, <SEP> 80/38
<tb> 201-0 <SEP> NaOH, <SEP> 15/24 <SEP> dunkelblau <SEP> 22
<tb> <B>10%</B> <SEP> Propansulton, <SEP> 30/49
<tb> 20% <SEP> NaOH, <SEP> 15/24 <SEP> dunkelblau <SEP> 23,5
<tb> <B>10%</B> <SEP> Propansulton, <SEP> 60/49
<tb> 20% <SEP> NaOH, <SEP> 15/24 <SEP> dunkelblau <SEP> 21
<tb> <B>10%</B> <SEP> Propansulton, <SEP> 15/71
<tb> 20% <SEP> NaOH, <SEP> 15/49 <SEP> dunkelblau <SEP> 25,5
<tb> 5 <SEP> % <SEP> Propansulton, <SEP> 30/49
<tb> 20% <SEP> NaOH,
<SEP> 15/24 <SEP> dunkelblau <SEP> 24
<tb> <B>25%</B> <SEP> Propansulton, <SEP> 30/49
Method for improving the dyeability of textile cellulose fibers The invention relates to a method for improving the dyeability of textile cellulose fibers, which is characterized in that
that the cellulose fibers are treated first with an aqueous alkali solution and then with a solution that contains a hydrocarbon sultone.
It is already known to treat sodium cellulose with hydrocarbon sultones. This gives a white, light mass with a fiber structure which is easily soluble in water.
It was therefore surprising that with the method according to the invention it was possible to obtain cellulose fibers whose dyeability was considerably better than that of untreated fibers or fibers treated only with sodium hydroxide, without the fibers noticeably losing their other textile properties.
The method according to the invention can be used for treating textile cellulose fibers of any type. These fibers can be in the form of woven and non-woven goods, threads, gauze, yarn, corduroy, cord, netting and the like. The process also includes the treatment of textile cellulose fibers that have already been pretreated, e.g. B. were merverized.
You can according to the invention treat fibers that contain any, preferably at least 30 percent, proportion of cellulose substances such as natural cellulose, eg. B. cotton or linen, or other cellulosic materials, such as viscose or copper ammonia rayon, regenerated cellulbs or cellulose acetate. If appropriate, the cellulose fibers can be mixed with wool and synthetic fibers, for.
B. with fibers made of acrylonitrile (Orlon, a 100% acrylonitrile polymer) or from vinylidenecyanide polymers or polyamides {nylon, from polyester-polyamides, from polymers of corn protein and formaldehyde, or from copolymers of the above-mentioned Mo nomeren, such.
B. Acrilan (85% acrylonitrile and <B> 15% </B> vinyl acetate), Dynel (60% vinyl chloride and 40% acrylonitrile), Saran (85% vinylidene chloride and 15% vinyl chloride). Also other synthetic materials or fibers made from polyalkylenes, such as polyethylene or polypropylene, polyurethane,
Mineral fibers (fiberglass) or alginic acid substances such as alginate redone can be used as additives to the cellulose fibers.
Preferred for use in the method of the invention are u. a. Textile fibers with at least 60 percent cellulose, which can consist in particular of cotton, rayon and cellulose acetate.
It has been found that, by using the method according to the invention, the cellulose-containing fiber material can be modified in such a way that it has a greatly increased reactivity towards other substances, such as basic dyes. The fibers treated according to the invention react with these without further ado and the dyeings obtained are deeper and more resistant to fading during exposure and washing.
When carrying out the method according to the invention, the cellulose fiber material to be treated is brought into contact with an aqueous alkali solution, preferably with a sodium hydroxide solution, which, however, can also be replaced by a potassium hydroxide or another alkali or alkaline earth solution can. The strength of the alkali solution can vary widely;
Concentrations between 1 and 30, in particular from 5 to 20% by weight are preferred. In the usual mercerization processes, alkali solutions are used in a concentration of 16 to 18%, which are also ideally suited for the process according to the invention.
In practice, the second stage of the process can immediately follow the mercerization stage and is therefore part of the normal wet treatment of textiles.
The impregnation or impregnation with the aqueous alkali can be carried out in any way, e.g. B. by dipping, spraying or padding. It is preferred to pull the material through the aqueous solution, as in the known padding technique. The amount of wet absorbed varies depending on the case; it is preferably from 20 to 100 parts of solution per 100 parts of dry material.
The temperature of the alkali solution and that of the material to be soaked. can be different; preferably both correspond approximately to the room temperature. Mercerization temperatures between 10 and 40 C are generally preferred.
The material soaked with the alkali solution is then treated with a solution of a sulton.
The sultones to be used according to the invention are intermolecular cyclic esters of hydroxysulfonic acids and can be derived from aliphatic, cycloaliphatic or aromatic acids.
Examples of sulfones which can be used according to the invention are the 1,3-propane sultones, the 1,4 butane sultones, the 1,3-hexane sultones and the benzyl and toluysultones, as well as mixtures thereof.
The sultones to be used can be the gamma sultones such as 1,3-propanesukone. The sultones can be prepared in a conventional manner, e.g.
B. by sulfochlorination of chlorinated hydrocarbons, where the resulting chlorosulfonic acid is then used for the formation of the sultones. The Sulton solutions can be prepared in any way, e.g.
B. by mixing the sultone with water, acetone or alcohol or mixtures thereof. In general, it is preferred to use an aqueous solution.
The concentration of the sultone solutions can be varied within a wide range; The use of solutions containing 1 to 25 percent by weight sultone is preferred.
It may be advantageous to add wetting agents, for which a large number of different compounds of cationic, anionic or nonionic character are available. Preferred are the ionic agents and in particular those with a polar structure,
in which a charged ionic group is bound to a hydrophilic (predominantly hydrocarbon) residue.
Such anionic surface-active compounds are u. a. the alkali and ammonium soaps of higher fatty acids, such as potassium or sodium myristate, laurate, palmitate, oleate or stearate or ammonium stearate;
The salts of long-chain aliphatic amines and quaternary ammonium bases, such as laurylamine hydrochloride and stearylamine hydrochloride, are also suitable. Examples of nonionic agents include: a. the partial esters of polyhydric alcohols and fatty acids, such as the hexitanes and hexitide esters, e.g. B.
Sorbitan monolaurate, the hydroxypolyoxyalkylene ethers of the above partial esters z. B. the polyethylene glycol ethers of sorbitan monolaurate, or the hydroxypolyoxyalkylene ethers of phenols, such as the reaction product of ethylene oxide and bisphenol-A or mixtures of the substances mentioned.
The wetting agents are preferably added in amounts of 0.1 to 5% by weight, in particular 0.5 to 3% by weight.
The impregnation of the alkali-pretreated fiber material can be done in any way, e.g. B. by dipping, spraying or padding. In general, it is useful to pull the fiber material through the sultoul solution, as is done with padding. The amount of solution absorbed can vary depending on the circumstances, but is preferably between 10 and 100%
The temperature of the Sulton and that of the soaked, alkaline pretreated fiber material can be varied within wide limits, for. B. between 15 and 90 C and is preferably between 20 and 70 C.
The time necessary for the reaction with the sulton depends on the temperature and the concentration of the solution. At elevated temperature, the reaction is complete in most cases within one or two hours.
After removing the impregnated material from the sultone solution, it is washed to remove the still adhering reactants, dried and is then immediately ready for dyeing. Washing is preferably carried out with water, to which cleaning agents (detergents) can optionally be added. Drying is best carried out at temperatures between room temperature and 125 C.
Example <I> 1 </I> A cotton fabric was treated for 15 minutes at 24 ° C. with 20% strength sodium hydroxide solution and then for 60 minutes at 49 ° C. with a 10% strength propane sulfone solution.
Cotton swatches measuring 7.5 × 7.5 cm were then dyed by semi-permanent boiling with 0.1% methylene blue and 0.1% acetic acid. The percentage reflection was determined; it is given in the table in comparison with that of the untreated goods and the goods treated only with alkali.
The following results were obtained:
EMI0003.0001
reflection
<tb> goods <SEP> color <SEP> in
<tb> untreated <SEP> royal blue <SEP> 44
<tb> only <SEP> with <SEP> 20% <SEP> NaOH <SEP> darker <SEP> blue
<tb> treats <SEP> as <SEP> above
<tb> treats <SEP> with <SEP> 20% <SEP> very <SEP> dark <SEP> blue
<tb> NaOH, <SEP> aftertreated
<tb> with <SEP> 10% <SEP> propane sulton <I> Example 2 </I> In further test series, the improved color absorption capacity of treated cotton fibers was shown,
using a less concentrated ribbon and varying amounts of propane sulton. The 7.5 x 7.5 cm swatches were boiled in 0.01% methylene blue with 0.01% acetic acid for 30 minutes. The results are shown in the table.
EMI0003.0015
Treatment, <SEP> min / cl <SEP> C <SEP> color <SEP> reflection
<tb> in
<tb> untreated <SEP> light blue <SEP> 69
<tb> 20% <SEP> NaOH, <SEP> 60/49 <SEP> light blue <SEP> 69
<tb> 20% <SEP> NaOH, <SEP> 60/49 <SEP> dark blue <SEP> 20 25% <SEP> propane sultone, <SEP> 90/24
<tb> 20% <SEP> NaOH, <SEP> 15/24 <SEP> dark blue <SEP> 19
<tb> <B> 10% </B> <SEP> propane sultone, <SEP> 80/38
<tb> 201-0 <SEP> NaOH, <SEP> 15/24 <SEP> dark blue <SEP> 22
<tb> <B> 10% </B> <SEP> propane sultone, <SEP> 30/49
<tb> 20% <SEP> NaOH, <SEP> 15/24 <SEP> dark blue <SEP> 23.5
<tb> <B> 10% </B> <SEP> propane sultone, <SEP> 60/49
<tb> 20% <SEP> NaOH, <SEP> 15/24 <SEP> dark blue <SEP> 21
<tb> <B> 10% </B> <SEP> propane sultone, <SEP> 15/71
<tb> 20% <SEP> NaOH, <SEP> 15/49 <SEP> dark blue <SEP> 25.5
<tb> 5 <SEP>% <SEP> propane sultone, <SEP> 30/49
<tb> 20% <SEP> NaOH,
<SEP> 15/24 <SEP> dark blue <SEP> 24
<tb> <B> 25% </B> <SEP> propane sultone, <SEP> 30/49
Claims (1)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US32309063A | 1963-11-12 | 1963-11-12 |
Publications (2)
Publication Number | Publication Date |
---|---|
CH1450164A4 CH1450164A4 (en) | 1966-05-31 |
CH422711A true CH422711A (en) | 1967-04-29 |
Family
ID=23257695
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH1450164A CH422711A (en) | 1963-11-12 | 1964-11-10 | Process for improving the dyeability of textile cellulose fibers |
CH50566A CH441215A (en) | 1963-11-12 | 1964-11-10 | Process for improving the crease resistance of textile cellulose fibers |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
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CH50566A CH441215A (en) | 1963-11-12 | 1964-11-10 | Process for improving the crease resistance of textile cellulose fibers |
Country Status (7)
Country | Link |
---|---|
US (1) | US3506390A (en) |
BE (1) | BE655568A (en) |
CH (2) | CH422711A (en) |
DE (1) | DE1469473A1 (en) |
FR (1) | FR1421620A (en) |
GB (1) | GB1035389A (en) |
NL (1) | NL6413072A (en) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3854867A (en) * | 1972-11-15 | 1974-12-17 | Us Agriculture | Process for reacting sultones with cellulosic materials to produce cellulosic materials having both basic and acidic groups and product produced |
US3854868A (en) * | 1972-11-15 | 1974-12-17 | Us Agriculture | Non-aqueous process for reacting sultones with cellulosic materials and the product produced |
GB8600676D0 (en) * | 1986-01-13 | 1986-02-19 | Sandoz Ltd | Organic compounds |
CN102251407B (en) * | 2011-06-09 | 2013-01-30 | 泰安市金飞虹织造有限公司 | Treatment method for alginate fiber fabric |
CN104988766A (en) * | 2015-06-24 | 2015-10-21 | 张家港市华阳针纺织品有限公司 | Processing technology of color-changing environment-friendly clothing fabric |
CN110080010B (en) * | 2019-02-26 | 2020-06-12 | 东华大学 | Preparation method of colored cellulose fibers |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
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BE570888A (en) * | ||||
DE1028527B (en) * | 1956-08-16 | 1958-04-24 | Boehme Fettchemie Gmbh | Process for the improvement of synthetically obtained molded articles containing carbonamide groups |
DE1146870B (en) * | 1961-07-24 | 1963-04-11 | Boehme Fettchemie Gmbh | Process for the production of propensultone |
-
1963
- 1963-11-12 US US323090A patent/US3506390A/en not_active Expired - Lifetime
-
1964
- 1964-11-10 DE DE19641469473 patent/DE1469473A1/en active Pending
- 1964-11-10 CH CH1450164A patent/CH422711A/en unknown
- 1964-11-10 CH CH50566A patent/CH441215A/en unknown
- 1964-11-10 GB GB45777/64A patent/GB1035389A/en not_active Expired
- 1964-11-10 BE BE655568D patent/BE655568A/xx unknown
- 1964-11-10 FR FR994464A patent/FR1421620A/en not_active Expired
- 1964-11-10 NL NL6413072A patent/NL6413072A/xx unknown
Also Published As
Publication number | Publication date |
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US3506390A (en) | 1970-04-14 |
CH441215A (en) | 1968-01-15 |
NL6413072A (en) | 1965-05-13 |
GB1035389A (en) | 1966-07-06 |
CH50566A4 (en) | 1967-01-31 |
DE1469473A1 (en) | 1970-03-19 |
FR1421620A (en) | 1965-12-17 |
BE655568A (en) | 1965-05-10 |
CH1450164A4 (en) | 1966-05-31 |
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