US3506390A - Process of reacting cellulosic fibers with sultones and optionally with other creaseproofing agents and resulting products - Google Patents
Process of reacting cellulosic fibers with sultones and optionally with other creaseproofing agents and resulting products Download PDFInfo
- Publication number
- US3506390A US3506390A US323090A US3506390DA US3506390A US 3506390 A US3506390 A US 3506390A US 323090 A US323090 A US 323090A US 3506390D A US3506390D A US 3506390DA US 3506390 A US3506390 A US 3506390A
- Authority
- US
- United States
- Prior art keywords
- sultone
- sultones
- fabric
- fabrics
- 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
- 238000000034 method Methods 0.000 title claims description 55
- 150000008053 sultones Chemical class 0.000 title claims description 32
- 239000000835 fiber Substances 0.000 title claims description 25
- 239000003795 chemical substances by application Substances 0.000 title description 15
- 238000004855 creaseproofing Methods 0.000 title description 13
- -1 HYDROCARBON SULTONE Chemical class 0.000 claims description 27
- 239000003518 caustics Substances 0.000 claims description 22
- 239000004215 Carbon black (E152) Substances 0.000 claims description 13
- 229930195733 hydrocarbon Natural products 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 12
- 239000012442 inert solvent Substances 0.000 claims description 3
- 239000004744 fabric Substances 0.000 description 76
- 239000000243 solution Substances 0.000 description 37
- 239000000463 material Substances 0.000 description 35
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- 239000002657 fibrous material Substances 0.000 description 23
- 229920000742 Cotton Polymers 0.000 description 22
- 239000004753 textile Substances 0.000 description 20
- FSSPGSAQUIYDCN-UHFFFAOYSA-N 1,3-Propane sultone Chemical compound O=S1(=O)CCCO1 FSSPGSAQUIYDCN-UHFFFAOYSA-N 0.000 description 18
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 11
- 239000007864 aqueous solution Substances 0.000 description 9
- 229920005989 resin Polymers 0.000 description 9
- 239000011347 resin Substances 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 8
- 239000003431 cross linking reagent Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- 230000009257 reactivity Effects 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 6
- 229920000877 Melamine resin Polymers 0.000 description 5
- 229920001807 Urea-formaldehyde Polymers 0.000 description 5
- 239000000981 basic dye Substances 0.000 description 5
- XVVGGZUZOITHPH-UHFFFAOYSA-N formaldehyde;prop-2-enal Chemical compound O=C.C=CC=O XVVGGZUZOITHPH-UHFFFAOYSA-N 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 229920000297 Rayon Polymers 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- WVJOGYWFVNTSAU-UHFFFAOYSA-N dimethylol ethylene urea Chemical compound OCN1CCN(CO)C1=O WVJOGYWFVNTSAU-UHFFFAOYSA-N 0.000 description 3
- 239000000975 dye Substances 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
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 3
- 239000005020 polyethylene terephthalate Substances 0.000 description 3
- 239000002964 rayon Substances 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 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
- 239000004952 Polyamide Substances 0.000 description 2
- 101001120757 Streptococcus pyogenes serotype M49 (strain NZ131) Oleate hydratase Proteins 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 229940083712 aldosterone antagonist Drugs 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 238000007598 dipping method Methods 0.000 description 2
- 238000002474 experimental method 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
- 229920000647 polyepoxide Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 229940035044 sorbitan monolaurate Drugs 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 229920002994 synthetic fiber Polymers 0.000 description 2
- 238000012360 testing method 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241000256844 Apis mellifera Species 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- SWJWLKWEBPOSQQ-UHFFFAOYSA-N C=O.NC(=O)N.C(=O)C=C Chemical compound C=O.NC(=O)N.C(=O)C=C SWJWLKWEBPOSQQ-UHFFFAOYSA-N 0.000 description 1
- 241000272165 Charadriidae Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229920004934 Dacron® Polymers 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
- 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
- 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
- 239000004902 Softening Agent Substances 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
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- GZCGUPFRVQAUEE-SLPGGIOYSA-N aldehydo-D-glucose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-SLPGGIOYSA-N 0.000 description 1
- 229940072056 alginate Drugs 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000005325 alkali earth metal hydroxides Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 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
- 230000015572 biosynthetic process Effects 0.000 description 1
- 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 1
- 238000009835 boiling Methods 0.000 description 1
- 235000012745 brilliant blue FCF Nutrition 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 229920001577 copolymer Polymers 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
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N dimethylmethane Natural products CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 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
- 229920001971 elastomer Polymers 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- IVJISJACKSSFGE-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine Chemical compound O=C.NC1=NC(N)=NC(N)=N1 IVJISJACKSSFGE-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- RNYJXPUAFDFIQJ-UHFFFAOYSA-N hydron;octadecan-1-amine;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[NH3+] RNYJXPUAFDFIQJ-UHFFFAOYSA-N 0.000 description 1
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 1
- 229940070765 laurate Drugs 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 239000002557 mineral fiber Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-M oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC([O-])=O ZQPPMHVWECSIRJ-KTKRTIGZSA-M 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- 239000000123 paper Substances 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
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 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
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229960003975 potassium Drugs 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229940045845 sodium myristate Drugs 0.000 description 1
- 229950005425 sodium myristyl sulfate Drugs 0.000 description 1
- JUQGWKYSEXPRGL-UHFFFAOYSA-M sodium;tetradecanoate Chemical compound [Na+].CCCCCCCCCCCCCC([O-])=O JUQGWKYSEXPRGL-UHFFFAOYSA-M 0.000 description 1
- UPUIQOIQVMNQAP-UHFFFAOYSA-M sodium;tetradecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCOS([O-])(=O)=O UPUIQOIQVMNQAP-UHFFFAOYSA-M 0.000 description 1
- 229940114926 stearate Drugs 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 239000004758 synthetic textile Substances 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
- 230000037303 wrinkles Effects 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 System; 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
Definitions
- This invention relates to the treatment of fibrous materials. More particularly, the invention relates to a process for treating cellulosic fibrous materials to improve their reactivity, to resulting products and to the use of the said products.
- the invention provides a new and improved process for treating cellulosic fibrous material, and particularly cellulosic textile products, to lmprove the reactivity to cross-linking agents and the like.
- This process comprises impregnating the desired fibrous materials with an aqueous caustic solution, and then treating the resulting impregnated fabric with an aqueous medium containing a sultone, and preferably a hydrocarbon sultone as propane sultone.
- the invention further provides the new and improved fibrous materials produced by this technique.
- the invention provides a technique for utilizing the above-described new cellulosic fibrous materials in preparing materials having improved crease and shrink resistance which comprises treating the above-described new cellulosic fibrous materials treated with the sultone to an aqueous medium containing a cellulosic treating agent such as, for example, polyepoxide-formaldehyde, acrolein-formaldehyde resins, urea-formaldehyde resin, and the like.
- a cellulosic treating agent such as, for example, polyepoxide-formaldehyde, acrolein-formaldehyde resins, urea-formaldehyde resin, and the like.
- the pad baths containing the urea resins have limited stability and must be used in a relatively short period of time. It is, therefore, highly desirable to develop some type of technique which would permit a higher degree of reactivity of the cellulosic fibers with the cross-linking agents using a bath of unlimited stability.
- the process of the invention which comprises impregnating the desired fibrous material with an aqueous caustic' solution and then treating the resulting impregnated material with an aqueous solution containing a sultone, and preferably propane sultone. It has been found that by this special technique that the cellulosic fibrous material may be modified so as to have greatly increased reactivity toward materials such as cross-linking agents, basic dyes and the like.
- the sultones used in the process of the invention are intermolecular cyclic esters of hydroxysulfonic acids and may be derived both from aliphatic, cycloaliphatic and aromatic acids.
- sultones suitable for the present process include 1,3-propane sultones, 1,4-butanesultones, 1,3-hexanesultones, benzylsultones, tolylsultone, and mixtures thereof.
- the present sultones to-be employed are the gamma sultones and preferablythe hydrocarbon sultones as 1,3-propane sultone.
- the sultones may be prepared by conventional techniques such as sulfochlorination of chlorinated hydrocarbons and subsequently using the resulting chlorosulfonic acid in the formation of the sultones. I
- the fibrous material to be treated is brought into contact. with an aqueous caustic solution.
- the caustic employed is preferably sodium hydroxide but potassium hydroxide or other alkali or alkali earth metal hydroxides may be utilized.
- the strength of the caustic solution may vary but preferred concentrations vary from about 1% to 30% by weight.
- Standard mecerizing procedures generally utilize concentrations of about 16-18% caustic and such solutions are ideally suited for the present process. In fact, the present process can follow the mercerizing step directly and thus fit into normal textile Wet processing mill practices. Overall preferred concentrations generally range from about 5.0% to 20% by weight.
- the impregnation with the aqueous caustic may be accomplished by any suitable means, such as, for example, by dipping, spraying, padding and the like. It is generally preferred to pass the fibrous material into and through the aqueous solution as by padding.
- the amount of Wet pick-up will vary with the different cases, but generally 3 it is preferred to have a wet-pick-up varying from about 20% to 100%.
- the temperature of the cautic solution as well as the temperature of the fibrous material to be impregnated may vary, but in general, it is preferred to have both at about ambient temperature. Mercerizing temperatures of about 50 F. to 100 F. are generally preferred.
- the material impregnated with the caustic material is then treated with an aqueous solution of the sultone.
- the solution of the sultone may be prepared in any manner such as mixing the sultone with water, acetone, alcohol and the like or mixtures thereof. It is generally preferred to employ an aqueous solution. Concentration of the sultone solution may vary over a wide range. It is generally preferred to employ solutions varying from about 1% to 25% by weight.
- wetting agents may be any of the known cationic, anionic or non-ionic materials and may have a great variety of different compositions.
- Preferred materials include the ionic agents and especially those having a polar structure including a hydrophilic (predominantly hydrocarbon) residue and a charged ionic radical thereon; such anionic surface active compounds include alkali metal and nitrogen-base soaps of higher fatty acids, such as potassium, and sodium myristate, laurate, palmitate, oleate, stearate, ammonium stearate, etc., as well as salts of long-chain aliphatic amines and quaternary ammonium bases, such as lauryl amine hydrochloride, stearyl amine hydrochloride, and the like.
- nonionic agents examples include the partial esters of polyhydric alcohols and fatty acids, such as the hexitans and hexitide esters as sorbitan monolaurate, hydroxypolyoxyalkylene ethers of the above-described partial esters as the polyethylene glycol ethers of sorbitan monolaurate, the hydroxypolyoxyalkylene ethers of phenols as the reaction product of ethylene oxide and bis-phenol-A and the like and mixtures thereof. These materials are preferably employed in amounts varying from about .l% to 5% by weight, and still more preferably f .om 0.5% to 3% by weight.
- the impregnation of the caustic treated fibrous material may be accomplished by any suitable means such as, for example, by dipping, spraying, padding and the like. It is generally preferred to pass the fibrous material into and through the sultone solution as by padding.
- the amount of wet pick-up Will vary with the different situations but generally is preferred to have a wet pick-up varying from to 100%.
- the temperature of the sultone solution as Well as the temperature of the caustic treated fibrous material to be impregnated may vary over a wide range. In general, the temperature may vary from about C. to 90 C. and more preferably between C. and 70 C.
- the length of time required for the reaction with the sultone may vary depending upon the temperature and concentration of solution. In most cases, at elevated temperatures the reaction can be completed within one or tWO hours.
- washing is preferably accomplished by use of water or water containing detergents and then drying at temperatures ranging from ambient temperature to 125 C.
- the material obtained by the above-described process will have the same appearance as before but will generally have a stilt feel and can be used as stiffening materials in a variety of different textile materials.
- the new material will also be characterized by having greater elongation.
- the material will have substantially the same strength and non-chlorine retaining properties as before the treatment.
- the fibrous material prepared by the process of the invention will have many active sufonic acid sites and as noted above are highly reactive toward many cross-linking agents and materials.
- examples of such materials include formaldehyde and resinous precondensates such as acrolein-formaldehyde, acrolein-urea-formaldehyde, formaldehyde reaction products with ethylene urea, melamine, and dicyandiamide.
- Other examples include the ketone aldehyde reaction products, poly epoxides, and the like. In the application of these materials to these impregnated fibrous materials any of the conventional techniques may be employed.
- the preferred techniques are generally to prepare an aqueous padding solution containing these agents and any desired additives such as softening agents and then pass the impregnated fibrous material into and through the solutions removing the excess solutions and curing the treated fabric.
- Concentrations of padding solutions generally vary from about 5% to about 25% with preferred concentrations ranging from 5% to 15%.
- Temperatures employed in the treatment will generally vary from about 20 C. to about C.
- Temperatures employed in the curing step will generally vary from 70 C. to C.
- the products treated as above may then be utilized for any of the intended applications.
- the textile materials for example, may be used in the manufacture of dresses, drapes, upholsteries, shoe fabrics, carpets, coats, shirts, uniforms, shoes, cords, construction fabrics and the like.
- the above-described process may be utilized for the treatment of any cellulosic fibrous material.
- This includes paper, wood and textile materials.
- the textile materials may be woven and non-woven fabrics, threads, gauze, yarn, cord, string, netting and the like.
- the process also includes treatment of materials which have been pretreated, e.g., mercerized.
- cellulosic material which has any part, and preferably at least 40%, derived from cellulosic materials, such as natural cellulose such as cotton, linen, and the like, and other cellulosics such as viscose rayon, cuprammonium rayon, regenerated cellulose, cellulosic acetate, as well as mixtures with wool, synthetics as fibers derived from acrylonitrile (Orlon- 100% acrylonitrile polymer), vinylidene cyanide polymers, polyamides (nylon-super polyamides), polyesterpolyamides, polymers prepared from corn protein and formaldehyde, as well as copolymers of the above monomers as, for example, Aerilan (85% acrylonitrile and 15% vinyl acetate), Dynel (60% vinyl chloride and 40% acrylonitrile), Saran (85 vinylidene chloride and 15 vinyl chloride), and other synthetic fabrics or fibers prepared from polyalkylenes as polyethylene, polypropylene, polyurethanes
- the preferred materials to be employed in the process include those textile materials containing at least 30% cellulosic materials and preferably those derived from cotton and rayon, and cellulose acetates.
- the wrinkle recovery values (MCRA) reported in the examples were determined by the Tentative Method of Test for Recovery of Textile Fabrics From Creasing, Using the Vertical Strip Apparatus, ASTM desig. D1295-53T (as reported as sum of average warp and fill measurements), and the tensile strength values were determined by Federal Specifications CCCT191.6, Instron Tensile Testing Machine, Method 5100. All tests were carried out at 65i2% relative humidity 20 and EXAMPLE I This example illustrates the treatment of cotton fabrics with a solution containing propane sultones.
- Cotton fabric 3.1 oz./sq. yard (80 x 80 count) was allowed to soak in a 20% sodium hydroxide solution for 15 minutes at room temperature. The fabric was then removed and the excess solution removed by squeezing through rubber coated squeeze rolls. The wet fabric was then placed in an impregnating solution made up of 25 grams of propane sultone, 75 grams of water and 3 grams sodium myristyl sulfate. The fabric was allowed to re main in this solution, for one-half hour at 120 F. It was then removed, the excess solution removed by squeezing through a squeeze roll and the fabric was then washed thoroughly and then dried 12 minutes at 250 F.
- the treated fabric which contained 0.49% sulfur as sulfonic acid was then passed into and through a solution containing of an acrolein-formaldehyde condensate which had been prepared by the method described in U.S. Patent 3,080,281.
- the treated fabric was cured by heating for 5-10 minutes at 325 F.
- the dried fabric was then examined to determine the crease resistance and the tensile strength. The results are shown in the following table:
- Cotton fabric was treated with 20% NaOH for 15 minutes at 75 F. and then with 10% propane sultone for 60 minutes at F. according to the technique set out in Example I. 3 x 3 inch swatches were then dyed by treating with 0.1% methylene blue and 0.1% acetic acid and boiling for /2 hour. The percent reflectance was determined and shown below in comparison to that of the untreated fabric and fabric treated only with the caustic.
- the resulting fabric was treated with a 10% aqueous solution of glycidyl ether of glycerol and cured at C. The resulting fabric had good crease resistance.
- Example I was repeated with the exception that the cotton fabric was replaced by a fabric made up of 35% cotton and 65% Dacron polyethylene terephthalate. Related results are obtained.
- a process for improving the properties of cellulosic fibers which comprises impregnating cellulosic fibers with an aqueous caustic solution and then treating the resulting fibers with a hydrocarbon sultone or mixtures of hydrocarbon sultones selected from the group consisting of lower alkyl hydrocarbon sultones, benzyl sultone, tolyl sultone and mixtures thereof in an inert solvent solution and reacting said fibers with said sultones while said fibers are wet with said caustic and sultone solutions.
- a process for preparing crease resistant textile fabrics which comprises treating cellulosic fibers in textile fabric form by the process of claim 1 and then treating the fabrics resulting from said process by creaseproofing said fabrics with a cellulosic, cross-linking creaseproofing agent, other than said sultones, in the absence of added catalyst for said creaseproofing agent.
- a process for improving the properties of cotton containing fabrics which comprises impregnating said fabrics with an aqueous sodium hydroxide solution which swells the cotton fibers in said fabrics and then treating the resulting fabrics with a hydrocarbon sultone or mixtures of hydrocarbon sultones selected from the group consisting of lower alkyl hydrocarbon sultones, benzyl sultone, tolyl sultone and mixtures thereof in an inert solvent solution and reacting said fibers with said sultones while said fibers are wet with said caustic an sultone solutions.
- a process for preparing cotton containing textile fabrics resistant to creasing in the wet or dry state which comprises treating the fabrics resulting from the process of claim 3 by creaseproofing said fabrics with a resinous condensate, cellulosic, cross-linking creaseproofing agent, other than said sultones, in the absence of added catalyst for said creaseproofing agent.
- a process for preparing crease resistant cotton textile fabrics which comprises impregnating said fabrics with an aqueous caustic solution and then treating the resulting fabrics with an aqueous solution of propane sultone and reacting said fabrics with said sultone while said fabrics are wet with said caustic and sultone solutions, and subsequently creaseproofing said fabrics with an aqueous solution of an acroleinformaldehyde condensate creaseproofing agent in the absence of added catalyst for said creaseproofing agent.
- a process for preparing crease resistant fabrics containing cellulosic fibers which comprises impregnating said fabrics with an aqueous sodium hydroxide solution and then treating the resulting fabrics with an aqueous solution of propane sultone and reacting said fabrics with said sultone while said fabrics are wet with said caustic and sultone solutions, and subsequently creaseproofing said fabrics with an aqueous solution of a creaseproofing agent selected from the group consisting of formaldehyde, urea-formaldehyde resins, melamine-formaldehyde resins, dicyandiamide-formaldehyde resins, acrolein-formaldehyde resins, ketone-formaldehyde resins and polyepoxides in the absence of added catalyst for said creaseproofing agent.
- a creaseproofing agent selected from the group consisting of formaldehyde, urea-formaldehyde resins, melamine-formal
- a process of improving the properties of cellulosic fibers which comprises impregnating cellulosic fibers with a lower alkyl hydrocarbon sultone and with an aqueous caustic solution and reacting said fibers with said sultone while said fibers are impregnated with said caustic solution.
Description
United States Patent Office 3,506,390 Patented Apr. 14, 1970 Int. (:1. D06m 9/00 us. (:1. 8115.7 15 Claims This invention relates to the treatment of fibrous materials. More particularly, the invention relates to a process for treating cellulosic fibrous materials to improve their reactivity, to resulting products and to the use of the said products.
Specifically, the invention provides a new and improved process for treating cellulosic fibrous material, and particularly cellulosic textile products, to lmprove the reactivity to cross-linking agents and the like. This process comprises impregnating the desired fibrous materials with an aqueous caustic solution, and then treating the resulting impregnated fabric with an aqueous medium containing a sultone, and preferably a hydrocarbon sultone as propane sultone. The invention further provides the new and improved fibrous materials produced by this technique.
As a special embodiment the invention provides a technique for utilizing the above-described new cellulosic fibrous materials in preparing materials having improved crease and shrink resistance which comprises treating the above-described new cellulosic fibrous materials treated with the sultone to an aqueous medium containing a cellulosic treating agent such as, for example, polyepoxide-formaldehyde, acrolein-formaldehyde resins, urea-formaldehyde resin, and the like.
It is known that many textile fabrics, such as cotton, have poor resilience, i.e., they are easily creased or wrinkled when crushed or otherwise subjected to localized physical pressure. In addition, many of these fabrics have poor dimensional stability as exemplified by poor resistance to shrinkage. In order to overcome these short comings, it as been common practice to treat the fabric with a resin such as an ureaor melamine-formaldehyde resin. While this method has met with some success, it has been found that the substantivity of the cross-linking agent to the fabric is in most cases non-existent and that strong catalysts and considerable cross-linking agent is needed in the reaction even to obtain a small degree of reactivity with the fabrics. In addition, the pad baths containing the urea resins have limited stability and must be used in a relatively short period of time. It is, therefore, highly desirable to develop some type of technique which would permit a higher degree of reactivity of the cellulosic fibers with the cross-linking agents using a bath of unlimited stability.
It is an object of the invention, therefore to provide a new method for treating textile materials. It is a further object to provide a method for treating fibrous materials to improve their reactivity toward cross-linking agents and other reactants. It is a further object to provide a method for modifying fibrous materials so that they will have improved reactivity to formaldehyde and to urea-formaldehyde, melamine-formaldehyde and acrolein-formaldehyde resins. It is a further object to provide a method for preparing cellulosic fabrics which have active acidic sites. It is a further object to provide a method for reaction of cellulosic materials with reactants which normally require an acid catalyst without the use of acidic catalysts. It is a further object to provide a process which utilizes a bath of unlimited stability. It is a further object to provide a method for treating textiles to improve their dyeability. It is a further object to provide a process for improving the hydrophilic properties of cellulosic fabrics. It is a further object to provide fibrous materials having improved wet and dry crease recovery. It is a further object to provide a method of modifying textile materials so that they might have increased stiffness. Other objects and advantages of the invention will be apparent from the following detailed description thereof.
It has now been discovered that these and other objects may be accomplished by the process of the invention which comprises impregnating the desired fibrous material with an aqueous caustic' solution and then treating the resulting impregnated material with an aqueous solution containing a sultone, and preferably propane sultone. It has been found that by this special technique that the cellulosic fibrous material may be modified so as to have greatly increased reactivity toward materials such as cross-linking agents, basic dyes and the like. It has been found, for example, that textile fabrics which have been treated according to this process are highly reactive toward agents such as formaldehyde, urea-formaldehyde resins, dimethylol ethylene urea, acroleinformaldehyde resins and melamine-formaldehyde resins, and rapidly react therewith to form materials having very high wet and dry crease recovery. It has been further found that the modified cellulosic material reacts with the cross-linking agents and other reactants without the use of conventional acidic catalysts. In addition, materials react readily with basic dyes which give colors which are deeper and more resistant to fading by light and washing. Further advantage is also found in the fact that the fibrous materials treated according to the process have greater stiffness and can be utilized as such for many important applications in the textile industry. Further, the new modified cellulosic products have residual strong acidity which permits further reaction or modification.
The sultones used in the process of the invention are intermolecular cyclic esters of hydroxysulfonic acids and may be derived both from aliphatic, cycloaliphatic and aromatic acids. Examples of sultones suitable for the present process include 1,3-propane sultones, 1,4-butanesultones, 1,3-hexanesultones, benzylsultones, tolylsultone, and mixtures thereof. The present sultones to-be employed are the gamma sultones and preferablythe hydrocarbon sultones as 1,3-propane sultone. The sultones may be prepared by conventional techniques such as sulfochlorination of chlorinated hydrocarbons and subsequently using the resulting chlorosulfonic acid in the formation of the sultones. I
According to the process of the invention, the fibrous material to be treated is brought into contact. with an aqueous caustic solution. The caustic employed is preferably sodium hydroxide but potassium hydroxide or other alkali or alkali earth metal hydroxides may be utilized. The strength of the caustic solution may vary but preferred concentrations vary from about 1% to 30% by weight. Standard mecerizing procedures generally utilize concentrations of about 16-18% caustic and such solutions are ideally suited for the present process. In fact, the present process can follow the mercerizing step directly and thus fit into normal textile Wet processing mill practices. Overall preferred concentrations generally range from about 5.0% to 20% by weight.
The impregnation with the aqueous caustic may be accomplished by any suitable means, such as, for example, by dipping, spraying, padding and the like. It is generally preferred to pass the fibrous material into and through the aqueous solution as by padding. The amount of Wet pick-up will vary with the different cases, but generally 3 it is preferred to have a wet-pick-up varying from about 20% to 100%.
The temperature of the cautic solution as well as the temperature of the fibrous material to be impregnated may vary, but in general, it is preferred to have both at about ambient temperature. Mercerizing temperatures of about 50 F. to 100 F. are generally preferred.
The material impregnated with the caustic material is then treated with an aqueous solution of the sultone. The solution of the sultone may be prepared in any manner such as mixing the sultone with water, acetone, alcohol and the like or mixtures thereof. It is generally preferred to employ an aqueous solution. Concentration of the sultone solution may vary over a wide range. It is generally preferred to employ solutions varying from about 1% to 25% by weight.
It is also desirable in some cases to employ wetting agents. These agents may be any of the known cationic, anionic or non-ionic materials and may have a great variety of different compositions. Preferred materials include the ionic agents and especially those having a polar structure including a hydrophilic (predominantly hydrocarbon) residue and a charged ionic radical thereon; such anionic surface active compounds include alkali metal and nitrogen-base soaps of higher fatty acids, such as potassium, and sodium myristate, laurate, palmitate, oleate, stearate, ammonium stearate, etc., as well as salts of long-chain aliphatic amines and quaternary ammonium bases, such as lauryl amine hydrochloride, stearyl amine hydrochloride, and the like. Examples of the nonionic agents include the partial esters of polyhydric alcohols and fatty acids, such as the hexitans and hexitide esters as sorbitan monolaurate, hydroxypolyoxyalkylene ethers of the above-described partial esters as the polyethylene glycol ethers of sorbitan monolaurate, the hydroxypolyoxyalkylene ethers of phenols as the reaction product of ethylene oxide and bis-phenol-A and the like and mixtures thereof. These materials are preferably employed in amounts varying from about .l% to 5% by weight, and still more preferably f .om 0.5% to 3% by weight.
The impregnation of the caustic treated fibrous material may be accomplished by any suitable means such as, for example, by dipping, spraying, padding and the like. It is generally preferred to pass the fibrous material into and through the sultone solution as by padding. The amount of wet pick-up Will vary with the different situations but generally is preferred to have a wet pick-up varying from to 100%.
The temperature of the sultone solution as Well as the temperature of the caustic treated fibrous material to be impregnated may vary over a wide range. In general, the temperature may vary from about C. to 90 C. and more preferably between C. and 70 C.
The length of time required for the reaction with the sultone may vary depending upon the temperature and concentration of solution. In most cases, at elevated temperatures the reaction can be completed within one or tWO hours.
After the impregnated material is removed from contact with the sultone solution it may then be washed to remove any excess reactants, dried and then used imme diately in the intended commercial applications. Washing is preferably accomplished by use of water or water containing detergents and then drying at temperatures ranging from ambient temperature to 125 C.
The material obtained by the above-described process will have the same appearance as before but will generally have a stilt feel and can be used as stiffening materials in a variety of different textile materials. The new material will also be characterized by having greater elongation. The material will have substantially the same strength and non-chlorine retaining properties as before the treatment.
The fibrous material prepared by the process of the invention will have many active sufonic acid sites and as noted above are highly reactive toward many cross-linking agents and materials. Examples of such materials include formaldehyde and resinous precondensates such as acrolein-formaldehyde, acrolein-urea-formaldehyde, formaldehyde reaction products with ethylene urea, melamine, and dicyandiamide. Other examples include the ketone aldehyde reaction products, poly epoxides, and the like. In the application of these materials to these impregnated fibrous materials any of the conventional techniques may be employed. The preferred techniques are generally to prepare an aqueous padding solution containing these agents and any desired additives such as softening agents and then pass the impregnated fibrous material into and through the solutions removing the excess solutions and curing the treated fabric. Concentrations of padding solutions generally vary from about 5% to about 25% with preferred concentrations ranging from 5% to 15%. Temperatures employed in the treatment will generally vary from about 20 C. to about C. Temperatures employed in the curing step will generally vary from 70 C. to C.
The products treated as above may then be utilized for any of the intended applications. The textile materials, for example, may be used in the manufacture of dresses, drapes, upholsteries, shoe fabrics, carpets, coats, shirts, uniforms, shoes, cords, construction fabrics and the like.
The above-described process may be utilized for the treatment of any cellulosic fibrous material. This includes paper, wood and textile materials. The textile materials may be woven and non-woven fabrics, threads, gauze, yarn, cord, string, netting and the like. The process also includes treatment of materials which have been pretreated, e.g., mercerized. By cellulosic is meant material which has any part, and preferably at least 40%, derived from cellulosic materials, such as natural cellulose such as cotton, linen, and the like, and other cellulosics such as viscose rayon, cuprammonium rayon, regenerated cellulose, cellulosic acetate, as well as mixtures with wool, synthetics as fibers derived from acrylonitrile (Orlon- 100% acrylonitrile polymer), vinylidene cyanide polymers, polyamides (nylon-super polyamides), polyesterpolyamides, polymers prepared from corn protein and formaldehyde, as well as copolymers of the above monomers as, for example, Aerilan (85% acrylonitrile and 15% vinyl acetate), Dynel (60% vinyl chloride and 40% acrylonitrile), Saran (85 vinylidene chloride and 15 vinyl chloride), and other synthetic fabrics or fibers prepared from polyalkylenes as polyethylene, polypropylene, polyurethanes, mineral fibers (Fiberglas), and alginic materials as alginate rayon.
The preferred materials to be employed in the process include those textile materials containing at least 30% cellulosic materials and preferably those derived from cotton and rayon, and cellulose acetates.
To illustrate the manner in which the invention may be carried out, the following examples are given. It is to be understood, however, that the examples are for the purpose of illustration and the invention is not to be regarded as limited to any of the specific materials or conditions recited therein.
The wrinkle recovery values (MCRA) reported in the examples were determined by the Tentative Method of Test for Recovery of Textile Fabrics From Creasing, Using the Vertical Strip Apparatus, ASTM desig. D1295-53T (as reported as sum of average warp and fill measurements), and the tensile strength values were determined by Federal Specifications CCCT191.6, Instron Tensile Testing Machine, Method 5100. All tests were carried out at 65i2% relative humidity 20 and EXAMPLE I This example illustrates the treatment of cotton fabrics with a solution containing propane sultones.
Cotton fabric 3.1 oz./sq. yard (80 x 80 count) was allowed to soak in a 20% sodium hydroxide solution for 15 minutes at room temperature. The fabric was then removed and the excess solution removed by squeezing through rubber coated squeeze rolls. The wet fabric was then placed in an impregnating solution made up of 25 grams of propane sultone, 75 grams of water and 3 grams sodium myristyl sulfate. The fabric was allowed to re main in this solution, for one-half hour at 120 F. It was then removed, the excess solution removed by squeezing through a squeeze roll and the fabric was then washed thoroughly and then dried 12 minutes at 250 F. The treated fabric which contained 0.49% sulfur as sulfonic acid was then passed into and through a solution containing of an acrolein-formaldehyde condensate which had been prepared by the method described in U.S. Patent 3,080,281. The treated fabric was cured by heating for 5-10 minutes at 325 F. The dried fabric was then examined to determine the crease resistance and the tensile strength. The results are shown in the following table:
Strip MCRA tensile,
lbs., warp/ Textile Wet Dry filling Untreated fabric 140 133 60/33 Fabric treated with propane sultone. 166 145 64/43 Propane sultone treated fabric plus acrolein-Ionnaldehyde resin 272 242 19/10 Untreated fabric plus acroleinformaldehyde without any added catalyst EXAMPLE II Example I was repeated with the exception that the resin used to treat the propane sultone treated fabric was dimethylol ethylene urea. The results are shown in the table below:
1 Strip MC RA tensile,
lbs., Warp/ Textile Wet Dry filling Untreated fabric 140 133 60/33 Propane sultone treated fabric treated with dimethylol ethylene urea 282 194 24/14 Untreated fabric plus dimethylol ethyl- Unchanged over untreated ene urea without acid catalyst fabric EXAMPLE III Example I was repeated with the exception that the conditions for the caustic treatment, the amount of the propane sultone and conditions for cure were modified as shown in the table below. The amount of sulfur was determined in each case to demonstrate the degree of reaction with the cellulose. The results are as indicated:
1st Step NaOH 2nd step Propane Sultone Sulfur,
percent w.
Percent Min./ F. Percent Min./ F. on fabric Untreated 01 fabric.
1 Treated fabric washed thoroughly to remove unreaeted materials.
6 EXAMPLE IV This experiment demonstrates the improved dye receptivity 30 obtained with the modified products of the present invention.
Cotton fabric was treated with 20% NaOH for 15 minutes at 75 F. and then with 10% propane sultone for 60 minutes at F. according to the technique set out in Example I. 3 x 3 inch swatches were then dyed by treating with 0.1% methylene blue and 0.1% acetic acid and boiling for /2 hour. The percent reflectance was determined and shown below in comparison to that of the untreated fabric and fabric treated only with the caustic.
Percent Fabric Color Reflectance Untreated Royal blue 44 Fagrigltireated only with 20% Darker blue than above 43 Fabric treated with 20% NaOH Very dark blue 1. 5
and 10% propane sultone as noted above.
EXAMPLE V An additional series of experiments were done to show the improved dye receptivity of the new products using a less concentrated dye bath and different amounts of propane sultone. The swatches were boiled 30 minutes in 0.01% methylene blue and 01% acetic acid. The results are indicated in the table below:
concentration of the sodium hydroxide was 17.6%, the concentration of the propane sultone was 10% and the propane sultone treating bath was 160 F. The resulting fabric was treated with a 10% aqueous solution of glycidyl ether of glycerol and cured at C. The resulting fabric had good crease resistance.
EXAMPLE VIII Example I was repeated with the exception that the cotton fabric was replaced by a fabric made up of 35% cotton and 65% Dacron polyethylene terephthalate. Related results are obtained.
I claim as my invention:
1. A process for improving the properties of cellulosic fibers which comprises impregnating cellulosic fibers with an aqueous caustic solution and then treating the resulting fibers with a hydrocarbon sultone or mixtures of hydrocarbon sultones selected from the group consisting of lower alkyl hydrocarbon sultones, benzyl sultone, tolyl sultone and mixtures thereof in an inert solvent solution and reacting said fibers with said sultones while said fibers are wet with said caustic and sultone solutions.
2. A process for preparing crease resistant textile fabrics which comprises treating cellulosic fibers in textile fabric form by the process of claim 1 and then treating the fabrics resulting from said process by creaseproofing said fabrics with a cellulosic, cross-linking creaseproofing agent, other than said sultones, in the absence of added catalyst for said creaseproofing agent.
3. A process for improving the properties of cotton containing fabrics which comprises impregnating said fabrics with an aqueous sodium hydroxide solution which swells the cotton fibers in said fabrics and then treating the resulting fabrics with a hydrocarbon sultone or mixtures of hydrocarbon sultones selected from the group consisting of lower alkyl hydrocarbon sultones, benzyl sultone, tolyl sultone and mixtures thereof in an inert solvent solution and reacting said fibers with said sultones while said fibers are wet with said caustic an sultone solutions.
4. A process for improving the properties of a cotton fabric as defined in claim 3 wherein the concentration of the sodium hydroxide solution varies from 5% to 25% by weight.
5. A process as in claim 3 wherein the hydrocarbon sultone is propane sultone.
6. A process as in claim 3 wherein the impregnation is accomplished at a temperature between 20 C. and 100 C.
7. A process as in claim 3 wherein the fabric is made up substantially of cotton.
8. A process as in claim 3 wherein the fabric is a mixture of cotton and polyethylene terephthalate.
9. A process for preparing cotton containing textile fabrics resistant to creasing in the wet or dry state which comprises treating the fabrics resulting from the process of claim 3 by creaseproofing said fabrics with a resinous condensate, cellulosic, cross-linking creaseproofing agent, other than said sultones, in the absence of added catalyst for said creaseproofing agent.
10. A process for preparing crease resistant cotton textile fabrics which comprises impregnating said fabrics with an aqueous caustic solution and then treating the resulting fabrics with an aqueous solution of propane sultone and reacting said fabrics with said sultone while said fabrics are wet with said caustic and sultone solutions, and subsequently creaseproofing said fabrics with an aqueous solution of an acroleinformaldehyde condensate creaseproofing agent in the absence of added catalyst for said creaseproofing agent.
11. A process for preparing crease resistant fabrics containing cellulosic fibers which comprises impregnating said fabrics with an aqueous sodium hydroxide solution and then treating the resulting fabrics with an aqueous solution of propane sultone and reacting said fabrics with said sultone while said fabrics are wet with said caustic and sultone solutions, and subsequently creaseproofing said fabrics with an aqueous solution of a creaseproofing agent selected from the group consisting of formaldehyde, urea-formaldehyde resins, melamine-formaldehyde resins, dicyandiamide-formaldehyde resins, acrolein-formaldehyde resins, ketone-formaldehyde resins and polyepoxides in the absence of added catalyst for said creaseproofing agent.
12. A process of improving the properties of cellulosic fibers which comprises impregnating cellulosic fibers with a lower alkyl hydrocarbon sultone and with an aqueous caustic solution and reacting said fibers with said sultone while said fibers are impregnated with said caustic solution.
13. The improved cellulosic fibers produced by the process of claim 1, said improved cellulosic fibers produced by said process being more acidic, more hydrophilic and more basic dye receptive than the untreated cellulosic fibers from which they were produced.
14. The improved cotton fabric produced by the process of claim 1 when the cellulosic fibers are in cotton fabric form, said improved cotton fabric produced by said process being more acidic, more hydrophilic and more basic dye receptive than the untreated cotton fabric from which it was produced.
15. The improved cotton fabric produced by the process of claim 5, said cotton fabric produced by said process being more acidic, more hydrophilic and more basic dye receptive than the untreated cotton fabric from which it was produced.
References Cited UNITED STATES PATENTS 2,989,364 6/1961 Goldann 8-1155 FOREIGN PATENTS 570,888 3/1959 Belgium. 1,146,870 4/ 1963 Germany.
DONALD LEVY, Primary Examiner US. Cl. X.R.
Claims (1)
1. A PROCESS FOR IMPROVING THE PROPERTIES OF CELLULOSIC FIBERS WHICH COMPRISES IMPREGNATING CELLULOSIC FIBERS WITH AN AQUEOUS CAUSTIC SOLUTION AND THEN TREATING THE RESULTING FIBERS WITH A HYDROCARBON SULTONE OR MIXTURES OF HYDROCARBON SULTONES SELECTED FROM THE GROUP CONSISTING OF LOWER ALKYL HYDROCARBON SULTONES, BENZYL SULTONE, TOLYL SULTONE AND MIXTURES THEREOF IN AN INERT SOLVENT SOLUTION AND REACTING SAID FIBERS WITH SAID SULTONES WHILE SAID FIBERS ARE WET WITH SAID CAUSTIC AND SULTONE SOLUTIONS.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US32309063A | 1963-11-12 | 1963-11-12 |
Publications (1)
Publication Number | Publication Date |
---|---|
US3506390A true US3506390A (en) | 1970-04-14 |
Family
ID=23257695
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US323090A Expired - Lifetime US3506390A (en) | 1963-11-12 | 1963-11-12 | Process of reacting cellulosic fibers with sultones and optionally with other creaseproofing agents and resulting products |
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) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3854868A (en) * | 1972-11-15 | 1974-12-17 | Us Agriculture | Non-aqueous process for reacting sultones with cellulosic materials and the product produced |
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 |
CN102251407A (en) * | 2011-06-09 | 2011-11-23 | 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 |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB8600676D0 (en) * | 1986-01-13 | 1986-02-19 | Sandoz Ltd | Organic compounds |
CN110080010B (en) * | 2019-02-26 | 2020-06-12 | 东华大学 | Preparation method of colored cellulose fibers |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE570888A (en) * | ||||
US2989364A (en) * | 1956-08-16 | 1961-06-20 | Bohme Fettchemie Gmbh | Process for the improvement of shaped thermoplastic materials 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 CH CH1450164A patent/CH422711A/en unknown
- 1964-11-10 GB GB45777/64A patent/GB1035389A/en not_active Expired
- 1964-11-10 FR FR994464A patent/FR1421620A/en not_active Expired
- 1964-11-10 BE BE655568D patent/BE655568A/xx unknown
- 1964-11-10 DE DE19641469473 patent/DE1469473A1/en active Pending
- 1964-11-10 CH CH50566A patent/CH441215A/en unknown
- 1964-11-10 NL NL6413072A patent/NL6413072A/xx unknown
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE570888A (en) * | ||||
US2989364A (en) * | 1956-08-16 | 1961-06-20 | Bohme Fettchemie Gmbh | Process for the improvement of shaped thermoplastic materials containing carbonamide groups |
DE1146870B (en) * | 1961-07-24 | 1963-04-11 | Boehme Fettchemie Gmbh | Process for the production of propensultone |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3854868A (en) * | 1972-11-15 | 1974-12-17 | Us Agriculture | Non-aqueous process for reacting sultones with cellulosic materials and the product produced |
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 |
CN102251407A (en) * | 2011-06-09 | 2011-11-23 | 泰安市金飞虹织造有限公司 | Treatment method for alginate fiber fabric |
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 |
Also Published As
Publication number | Publication date |
---|---|
NL6413072A (en) | 1965-05-13 |
BE655568A (en) | 1965-05-10 |
GB1035389A (en) | 1966-07-06 |
CH441215A (en) | 1968-01-15 |
CH422711A (en) | 1967-04-29 |
CH50566A4 (en) | 1967-01-31 |
CH1450164A4 (en) | 1966-05-31 |
FR1421620A (en) | 1965-12-17 |
DE1469473A1 (en) | 1970-03-19 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US2436076A (en) | Method of stabilizing against shrinkage textile materials of regenerated cellulose | |
US3183054A (en) | Aldehyde condensation products and their use in treating fibrous materials | |
US3220869A (en) | Process for improving textile fabrics | |
US2985501A (en) | Process of producing flat drying, wet crease resistant cellulosic fabrics by reaction with cross-linking agents and products produced thereby | |
US3218118A (en) | Crease-proofing cellulosic fabrics, the fabrics obtained and methods of making them | |
US3472606A (en) | Two-component wet fixation process for imparting durable press to cellulosecontaining materials | |
US2158494A (en) | Treatment of textile materials | |
US3458869A (en) | Method of producing press-free garments and products thereof | |
US3506390A (en) | Process of reacting cellulosic fibers with sultones and optionally with other creaseproofing agents and resulting products | |
US3434794A (en) | Delayed cure of cellulosic articles | |
Reeves et al. | Poly-set process for producing durable-press cotton goods 1 | |
US3510247A (en) | Modification of cellulosic materials with tertiary bis-acrylamides | |
US3933426A (en) | Process for making textiles containing cellulose crease-resistant | |
US3627556A (en) | Durable press finish for wool/cellulosic fabrics (melamine/dihydroxy-imidazolidinone resins) | |
US3402988A (en) | Chemical deactivation of catalyst at both faces of a cellulosic fabric impregnated with a resin-catalyst system to improve abrasion resistance of fabric after curing | |
US3617197A (en) | Improving the wrinkle resistance of cellulosic textiles | |
US3026216A (en) | Treatment of textile fabrics with methylglycidyl ethers | |
Lewin et al. | The role of liquid ammonia in functional textile finishes | |
EP0268368B1 (en) | Fabric treatment | |
US3175875A (en) | Cellulosic fabrics and methods for making the same | |
US5135541A (en) | Flame retardant treatment of cellulose fabric with crease recovery: tetra-kis-hydroxy-methyl phosphonium and methylolamide | |
US4346127A (en) | Process for preparing absorbing mop material of non-woven fibres and polymeric binder | |
US2904387A (en) | Composition and process for crease- and wrinkleproofing cellulosic textile material | |
US3039167A (en) | Method for improving the properties of fabrics containing cross-linked regenerated cellulose material | |
US3041199A (en) | Wrinkle resistant cellulose fabric and method of production |