US2982751A - Process and composition for rendering synthetic hydrophobic material antistatic and the product obtained therefrom - Google Patents
Process and composition for rendering synthetic hydrophobic material antistatic and the product obtained therefrom Download PDFInfo
- Publication number
- US2982751A US2982751A US774137A US77413758A US2982751A US 2982751 A US2982751 A US 2982751A US 774137 A US774137 A US 774137A US 77413758 A US77413758 A US 77413758A US 2982751 A US2982751 A US 2982751A
- Authority
- US
- United States
- Prior art keywords
- parts
- fabric
- composition
- polyamine
- antistatic
- 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
- 239000000203 mixture Substances 0.000 title claims description 21
- 230000002209 hydrophobic effect Effects 0.000 title claims description 14
- 239000000463 material Substances 0.000 title description 11
- 238000000034 method Methods 0.000 title description 6
- 238000009877 rendering Methods 0.000 title description 2
- 229920000768 polyamine Polymers 0.000 claims description 17
- 229920000647 polyepoxide Polymers 0.000 claims description 14
- 230000003068 static effect Effects 0.000 claims description 7
- 230000005611 electricity Effects 0.000 claims description 4
- 238000009825 accumulation Methods 0.000 claims description 2
- 239000004744 fabric Substances 0.000 description 28
- 239000004753 textile Substances 0.000 description 13
- -1 poly(allyl glycidyl ethers Chemical class 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- 239000000839 emulsion Substances 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 8
- 239000000376 reactant Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000004061 bleaching Methods 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 238000005406 washing Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229920001223 polyethylene glycol Polymers 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 5
- 239000002202 Polyethylene glycol Substances 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 150000002118 epoxides Chemical class 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 229920002972 Acrylic fiber Polymers 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000007844 bleaching agent Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
- 239000005020 polyethylene terephthalate Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 239000002216 antistatic agent Substances 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000005108 dry cleaning Methods 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 238000009991 scouring Methods 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- GODZNYBQGNSJJN-UHFFFAOYSA-N 1-aminoethane-1,2-diol Chemical compound NC(O)CO GODZNYBQGNSJJN-UHFFFAOYSA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- WIFVBBXWAWZSJA-UHFFFAOYSA-N 1-n-(2-aminopropyl)propane-1,2-diamine Chemical compound CC(N)CNCC(C)N WIFVBBXWAWZSJA-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- 239000000263 2,3-dihydroxypropyl (Z)-octadec-9-enoate Substances 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- RZRNAYUHWVFMIP-GDCKJWNLSA-N 3-oleoyl-sn-glycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](O)CO RZRNAYUHWVFMIP-GDCKJWNLSA-N 0.000 description 1
- QVIAMKXOQGCYCV-UHFFFAOYSA-N 4-methylpentan-1-amine Chemical compound CC(C)CCCN QVIAMKXOQGCYCV-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229920001634 Copolyester Polymers 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- MFIBZDZRPYQXOM-UHFFFAOYSA-N [dimethyl-[3-(oxiran-2-ylmethoxy)propyl]silyl]oxy-dimethyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical group C1OC1COCCC[Si](C)(C)O[Si](C)(C)CCCOCC1CO1 MFIBZDZRPYQXOM-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- UPCIBFUJJLCOQG-UHFFFAOYSA-L ethyl-[2-[2-[ethyl(dimethyl)azaniumyl]ethyl-methylamino]ethyl]-dimethylazanium;dibromide Chemical compound [Br-].[Br-].CC[N+](C)(C)CCN(C)CC[N+](C)(C)CC UPCIBFUJJLCOQG-UHFFFAOYSA-L 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229940005740 hexametaphosphate Drugs 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- RZRNAYUHWVFMIP-UHFFFAOYSA-N monoelaidin Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- UKLNMMHNWFDKNT-UHFFFAOYSA-M sodium chlorite Chemical compound [Na+].[O-]Cl=O UKLNMMHNWFDKNT-UHFFFAOYSA-M 0.000 description 1
- 229960002218 sodium chlorite Drugs 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- MNCGMVDMOKPCSQ-UHFFFAOYSA-M sodium;2-phenylethenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C=CC1=CC=CC=C1 MNCGMVDMOKPCSQ-UHFFFAOYSA-M 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 229960001124 trientine Drugs 0.000 description 1
- SOBHUZYZLFQYFK-UHFFFAOYSA-K trisodium;hydroxy-[[phosphonatomethyl(phosphonomethyl)amino]methyl]phosphinate Chemical compound [Na+].[Na+].[Na+].OP(O)(=O)CN(CP(O)([O-])=O)CP([O-])([O-])=O SOBHUZYZLFQYFK-UHFFFAOYSA-K 0.000 description 1
- 238000004078 waterproofing Methods 0.000 description 1
- 238000009941 weaving Methods 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01G—HORTICULTURE; CULTIVATION OF VEGETABLES, FLOWERS, RICE, FRUIT, VINES, HOPS OR SEAWEED; FORESTRY; WATERING
- A01G9/00—Cultivation in receptacles, forcing-frames or greenhouses; Edging for beds, lawn or the like
- A01G9/24—Devices or systems for heating, ventilating, regulating temperature, illuminating, or watering, in greenhouses, forcing-frames, or the like
- A01G9/241—Arrangement of opening or closing systems for windows and ventilation panels
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/04—Coating
- C08J7/0427—Coating with only one layer of a composition containing a polymer binder
-
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/08—Heat treatment
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- D—TEXTILES; PAPER
- D04—BRAIDING; LACE-MAKING; KNITTING; TRIMMINGS; NON-WOVEN FABRICS
- D04H—MAKING TEXTILE FABRICS, e.g. FROM FIBRES OR FILAMENTARY MATERIAL; FABRICS MADE BY SUCH PROCESSES OR APPARATUS, e.g. FELTS, NON-WOVEN FABRICS; COTTON-WOOL; WADDING ; NON-WOVEN FABRICS FROM STAPLE FIBRES, FILAMENTS OR YARNS, BONDED WITH AT LEAST ONE WEB-LIKE MATERIAL DURING THEIR CONSOLIDATION
- D04H1/00—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres
- D04H1/40—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres from fleeces or layers composed of fibres without existing or potential cohesive properties
- D04H1/54—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres from fleeces or layers composed of fibres without existing or potential cohesive properties by welding together the fibres, e.g. by partially melting or dissolving
-
- 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
- D06M13/322—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 nitrogen
- D06M13/372—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 nitrogen containing etherified or esterified hydroxy groups ; Polyethers of low molecular weight
-
- 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
- D06M13/322—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 nitrogen
- D06M13/385—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 nitrogen containing epoxy groups
-
- 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
-
- 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
- D06M15/55—Epoxy 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
- D06M23/00—Treatment of fibres, threads, yarns, fabrics or fibrous goods made from such materials, characterised by the process
-
- 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
- D06M23/00—Treatment of fibres, threads, yarns, fabrics or fibrous goods made from such materials, characterised by the process
- D06M23/06—Processes in which the treating agent is dispersed in a gas, e.g. aerosols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2323/00—Characterised by the use of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Derivatives of such polymers
- C08J2323/02—Characterised by the use of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Derivatives of such polymers not modified by chemical after treatment
- C08J2323/04—Homopolymers or copolymers of ethene
- C08J2323/06—Polyethene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2477/00—Characterised by the use of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Derivatives of such polymers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A40/00—Adaptation technologies in agriculture, forestry, livestock or agroalimentary production
- Y02A40/10—Adaptation technologies in agriculture, forestry, livestock or agroalimentary production in agriculture
- Y02A40/25—Greenhouse technology, e.g. cooling systems therefor
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/04—Polyester fibers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/09—Polyolefin
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/10—Polyvinyl halide esters or alcohol fiber modification
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/21—Nylon
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2913—Rod, strand, filament or fiber
- Y10T428/2915—Rod, strand, filament or fiber including textile, cloth or fabric
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2913—Rod, strand, filament or fiber
- Y10T428/2933—Coated or with bond, impregnation or core
- Y10T428/2964—Artificial fiber or filament
- Y10T428/2967—Synthetic resin or polymer
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2913—Rod, strand, filament or fiber
- Y10T428/2933—Coated or with bond, impregnation or core
- Y10T428/2964—Artificial fiber or filament
- Y10T428/2967—Synthetic resin or polymer
- Y10T428/2969—Polyamide, polyimide or polyester
Definitions
- This invention relates to new compositions ofmatter. More particularly it is concerned with a synthetic, hydrophobic shaped structure bearing a novel finish to minimize the accumulation of charges of static electricity during finishing operations andnormal use.
- polyethylene glycol dihalide e.g'. chloride, bromide or iodide
- analogue is condensed v(with release of hydrogen halide) with an amine, the nitrogen of which contains at least two active hydrogen.
- Typical of such amines are methylamine, ethylamine, propylamine, butylamine, amylamine, hexylamine, dodecylamine, 'allylamine, monoethanolamine, 3-isopropyl-n-propylamine, S-methoxy-npropylamine, d-iethylenetriamine, ,bis(3 aminopropyl)- other common yarn-treating agents which are not stable in that pH range, making it necessary to apply the agent in a treatment step distinct from that employed for other purposes.
- a further object is to provide a treated synthetic, hydrophobic shaped structure which minimizes or eliminates build-up of electrostatic charge and otherwise possesses substantially the same properties as the same structure before treatment.
- Another object is to provide a process for imparting durable antistatic properties to a synthetic, hydrophobic shaped structure.
- epoxide curing By epoxide curing? is meant that the polyamine defined above is reacted, after application of the reactants to the said shaped structure, with a polyepoxide.
- Such materials can be prepared by condensing epichlorohydrin with a polyol.
- a typical example is the condensation product (with elimination of HCl) of glycerine and epichlorohydrin. Preparation of these products is'described in detail in British Patent 780,288, dated July 31, 1957.
- Epon resins whichare diepoxide condensation products of epichlorohydrinand dimethyl, di-para hydroxyphenyl methane and the poly(allyl glycidyl ethers).
- a typical siloxane is 1,3- bis-[-3-(2,3 epoxy propoxy) propyl]tetramethyldisiloxane sold under the trademark Syl-Kem 90 by Dow Corning Corp, Midland, Michigan. Reaction of the polyamine (I) or (II) with the polyepoxide may be conveniently accomplishedby heating the shaped structure to which the mixture of the amine and polyepoxide has been applied.
- the washed fabrics are washed in a Kenmore portable Such materials are available on the open marwasher at 140 F. using 0.125% Tide detergent in the presence of a small amount of trisodium hexametaphosphate, then thoroughly rinsed and dried.
- the dry cleaning operation employed involves a -minute tumble at room temperature using a solution of the followingrfabricin 100 times its'weight of bleaching bath containing:
- the pHof the resulting solution is adjusted to 3:2 by addition'of '70 parts of a 10% solution of hydrochloric acid in w'at'er. 62 parts of Eponite 100 as identified above is then added and the mixture is dispersed using a Waring 'Blen'dor. While mixing in the Waring Blendor, 4 parts of zinc fluoroborate catalyst as a 40% aqueous solution is added. A stable homogeneous emulsion is formed.
- a swatch of tropical plain weave fabric woven from a polyethylene terephthalate yarn is dipped into the emulsion prepared as described above and squeezed between the rollers of a hand wringer.
- the fabric is then cured for 5 minutes in an oven, at. j160 C. and thereafter scoured for 15 minutes at F.
- the fabric is 0bse'rved'to have gained 3.2% by weight of antistatic finish based on the original'weight of the fabric; 'Tlie treated fabric has a Log R of 10.3' compared Withan' original Log R of 14.2.
- the sam: plc is observed to have a Log R of 12.9.
- a 21% by weight finish based on theweight of the fabric is attained when 1240 parts of' Eponite 100" is employfid using the technique described above. In this case 80 parts of the zinc fluoroborate catalyst is employed.
- the product has a Log R of 11.0 before the standard bleaching and a Log R of 11.5 after the bleaching,- EXAMPLE "2
- Example 1 ismodified by employing as the 'polyarnine component the reaction product of the dichloride of polyethylene glycol having a molecularweight of 600 with methyl amine (Aston 108 as identified above); The percent by 'weight of finish picked upby' the fabric samples as well as LogRs before and after standard bleaching when using 62 parts of the diepoxide (A) and when using 1240 parts of the'diepoxid'elB) are shown inT-ableI.
- the finish is applied using -a laboratory-padder'set at 50 lbs. persquare inch providing two dips and twonips. After padding all. fabric samples are dried overnight at room temperature and thereafter cured for 6 minutes at C.
- Thein'itial L'o'g R of theisamples, the percent by weight of antistatic agent deposited "based on the weight of the fabric 'an'd'the Log Robservation's before and after washing, bleaching anddry cleaning are shown inTableIII.
- Comparative figures for similar samples treated in accordance with the present invention are included in the table.
- the samples treated with the finish cross-linked with the diiodide are labeled C1, D and E
- the table shows a comparative figure of yellowness factor relative to samples C and C D and D
- samples H, I and .1 results in re-v duction of the color of the samples to less than that of the control.
- optical whiteners and silicone water proofing agents and other commonly used Examples 1 and 2 are: modified by employing as: the curing agent 62 parts of Syl-Kem 90 as identified above.
- the Log R of the samples M "and N respectively before scouring, after scouring and after 5 hours wash are reported in Table VI.
- a polyepoxide resin is preparedby mixing 15 parts 1.1 11.9 12.4 of sodium styrene sulfonate, 80 parts of diionized water, 2 0.15 part of glyceryl monooleate, .08- part of alkyl' phenoxy polyoxyethanol and 1 .67- parts of glycidyl EXAMPLE 4 methacrylate in a Waring Blendor to; form anemulsion.
- Epon Resin 562 is omitted from one solution of polyethylene glycol amine, and' similarly, a 1% solution of Epon Resin 5 62 is prepared, omitting the poly-amine. All solutions are acidified to pH 2.5 with HCl, including apure water control containing no other ingredients. Samples of a tow of continuous filaments formed from a polymer of acrylonitrile (i.e. Orlon as identified above) are dipped into the test solutions at room temperature, wrung out to a solution pick-up of 100% and cured in a drying oven at 270 F. for ten minutes. The cured tow is converted into staple pads suitable for washing and testing for antistatic properties.
- a polymer of acrylonitrile i.e. Orlon as identified above
- washing tests are carried out with 0.1% aqueous Tide using a 15-minute wash cycle at The emulsion is added: to a 200 ml. 3-necked. flask which is then flushed with nitrogen. .06 part of a,a'aZ0biSiS0 butyryl nitrile is then added and the reaction mass is heated for 3 hours at 70 C. A thick semitransparent emulsion is formed.
- EXAMPLE 7' The technique of Example 4. is. followed in preparing; three antistatic finish reactants (M, N and 0) containing, the polyamine and diepoxide resin in a 1:1 weight ratio. Aston LT is employed as the polyamine in each applica-- tion. The emulsions are applied to a fabric. woven from a polymer of acrylonitrile (i.e.- Orlon as identified:- above) having an initial b; of 3.0.
- M, N and 0 antistatic finish reactants
- Aston LT is employed as the polyamine in each applica-- tion.
- the emulsions are applied to a fabric. woven from a polymer of acrylonitrile (i.e.- Orlon as identified:- above) having an initial b; of 3.0.
- diepoxide curing agent employed in each example is identified in Table- VII
- the color and ILog R ofeach sample after curing is reported inT'able Y 1
- EXAMPLE 8 A mixture of 50 parts'of Aston 108 (20% active ingredients), 10 parts Eponite 100 and 940 parts water is made up and adjusted to pH 3.5. A tow formed from a polymer of acrylonitrile (i.e. Orlon as identified above) is treated to provide a 100% by weight Wet pickup of this solution, then cut into staple and dried at 270 F. for ten minutes. 20 parts of this treated staple is then blended with 80 parts untreated staple and the blend is spun into yarn and woven into a twill fabric. Samples of the fabric are washed, tested, bleached, disperse dyed and basic dyed. All exhibit static protection after 10 washes as shown in Table IX.
- G and G are divalent hydrocarbon radicals.
- Typical polyamides and processes for their production are described in United States Patents Nos. 2,071,250; 2,071,253 and 2,130,948.
- polyacrylonitrile i.e., the homopolymer
- polyesters from which such structures may be devised include polyethylene terephthalate, polyethylene terephthalate copolyesters prepared using polyethylene glycols such as polyethylene vglycols having molecular weights of to about 6,000, or polyethers such as the dicarboxymethyl acid of polytetramethylene oxide or the esters polytetramethylene oxide, polydioxalane, or polyesters prepared using other acids such as bibenzoic, isophthalic or ethylene-bis-p-oxybenzoic acids.
- polyethylene glycols such as polyethylene vglycols having molecular weights of to about 6,000
- polyethers such as the dicarboxymethyl acid of polytetramethylene oxide or the esters polytetramethylene oxide, polydioxalane
- polyesters prepared using other acids such as bibenzoic, isophthalic or ethylene-bis-p-oxybenzoic acids.
- Such materials are described in United States Patent No. 2,465,319.
- antistatic finish of the presentinvention may be made to any form of the shaped structure including foams, fabric, yarn, tow, staple, films, plastic sheeting and the like.
- the shaped structure is treated with an emulsion of a mixture of a polyepoxide and a compound of Formula I.
- the emulsion is prepared by dispersing the polyamine and the polyepoxide in water at room temperature with vigorous stirring.
- the concentration of reactants in the emulsion- may vary widely. A concentration as high as 20% maybe used. However, more dilute emulsions containing from about 1 to about 5% of reactants are generally preferred. Any such finishing suspension having a concentration suitable to provide from about a 0.3% to about a 5% solids iokup based on the dry material is satisfactory.
- the reaction product can be applied to the structure by conventional methods such as dipping, padding, brushing, spraying, and the like. After removal of excess liquid, by wringing in the case of a textile, it is usually convenient to dry and cure the structure in one operation.
- the proportion of components may vary over a wide range.
- the ratio of polyarnine:polyepoxide is maintained within the limits of 10:3 to 10:7. Higher ratios of polyepoxide such as 1:1 may be used however, as illustrated in the examples. Larger amounts of the polyepoxide may be employed but generally result in a harsher hand.
- the reactants may be ap-- plied to the shaped structure without the presence of catalysts, it is preferred to include a minor amount of an epoxide curing catalyst.
- an epoxide curing catalyst Such materials not only hasten the curing operation or permit curing at lower temperature, but also increase adherence of the antistatic agent to the structure.
- Such materials are well known in the art, as described, for instance in United States Patent No. 2,752,269.
- the reactant mixture may be either acidic or alkaline, alkaline conditions usually cause yellowing.
- Optimum conditions of curing will depend upon the identity of the reactants, the identity of the textile and whether or not a catalyst is included. Room temperature is adequate for forming the cured antistatic finish when a catalyst is used. Generally, however, a temperature of at least about 240 F. is preferred to accomplish eflicient drying of the textile. Usually temperature adjustment is made to permit curing and drying in a 3- minute interval. A temperature of about 212 F. to 250 F. is recommended for most textile materials. For operation in the absence of a catalyst a curing cycle of about 10 minutes at 270 F. is adequate.
- a composition suitable for minimizing the accumula- 9 tion of charge of static electricity of a hydrophobic shaped structure comprising a mixture of a polyepoxide and a polyamine of the formula:
- composition of claim 1 wherein the polyepoxide is a reaction product of glycerin and epichlorohydrin.
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Dispersion Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Environmental Sciences (AREA)
- Physics & Mathematics (AREA)
- Thermal Sciences (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Priority Applications (13)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NL245471D NL245471A (de) | 1958-11-17 | ||
US774138A US3021232A (en) | 1958-11-17 | 1958-11-17 | Process for rendering synthetic hydrophobic material antistatic and the product obtained therefrom |
US774137A US2982751A (en) | 1958-11-17 | 1958-11-17 | Process and composition for rendering synthetic hydrophobic material antistatic and the product obtained therefrom |
US794813A US3053609A (en) | 1958-11-17 | 1959-02-24 | Textile |
BE584710D BE584710A (de) | 1958-11-17 | 1959-11-16 | |
FR810279A FR1243990A (fr) | 1958-11-17 | 1959-11-16 | Compositions antistatiques, notamment pour matières et articles hydrophobes |
DEP23902A DE1147910B (de) | 1958-11-17 | 1959-11-17 | Verfahren zur Verringerung der Ansammlung elektrostatischer Ladungen auf hydrophoben Stoffen |
GB39001/59A GB923645A (en) | 1958-11-17 | 1959-11-17 | Antistatic compositions for hydrophobic shaped structures |
DK464459AA DK106547C (da) | 1958-11-17 | 1959-12-21 | Fremgangsmåde til punktbinding af fibermateriale i uforarbejdet eller forarbejdet tilstand ved behandling med et opløsningsmiddel for fibrene. |
NL246633D NL246633A (de) | 1958-11-17 | 1959-12-21 | |
GB43605/59A GB911282A (en) | 1958-11-17 | 1959-12-22 | Processes for the treatment of fibrous materials |
CH8221959A CH381193A (de) | 1958-11-17 | 1959-12-22 | Verfahren zur Verfestigung von Textilien und einphasige Lösung zur Durchführung dieses Verfahrens |
FR814013A FR1260024A (fr) | 1958-11-17 | 1959-12-23 | Procédé de traitement de fils et tissus en vue d'améliorer leur aspect à l'aide de solutions susceptibles de les agglutiner par points |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US774137A US2982751A (en) | 1958-11-17 | 1958-11-17 | Process and composition for rendering synthetic hydrophobic material antistatic and the product obtained therefrom |
US774138A US3021232A (en) | 1958-11-17 | 1958-11-17 | Process for rendering synthetic hydrophobic material antistatic and the product obtained therefrom |
US78241258A | 1958-12-23 | 1958-12-23 | |
US794813A US3053609A (en) | 1958-11-17 | 1959-02-24 | Textile |
Publications (1)
Publication Number | Publication Date |
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US2982751A true US2982751A (en) | 1961-05-02 |
Family
ID=27505730
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US774137A Expired - Lifetime US2982751A (en) | 1958-11-17 | 1958-11-17 | Process and composition for rendering synthetic hydrophobic material antistatic and the product obtained therefrom |
US774138A Expired - Lifetime US3021232A (en) | 1958-11-17 | 1958-11-17 | Process for rendering synthetic hydrophobic material antistatic and the product obtained therefrom |
US794813A Expired - Lifetime US3053609A (en) | 1958-11-17 | 1959-02-24 | Textile |
Family Applications After (2)
Application Number | Title | Priority Date | Filing Date |
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US774138A Expired - Lifetime US3021232A (en) | 1958-11-17 | 1958-11-17 | Process for rendering synthetic hydrophobic material antistatic and the product obtained therefrom |
US794813A Expired - Lifetime US3053609A (en) | 1958-11-17 | 1959-02-24 | Textile |
Country Status (8)
Country | Link |
---|---|
US (3) | US2982751A (de) |
BE (1) | BE584710A (de) |
CH (1) | CH381193A (de) |
DE (1) | DE1147910B (de) |
DK (1) | DK106547C (de) |
FR (2) | FR1243990A (de) |
GB (2) | GB923645A (de) |
NL (2) | NL246633A (de) |
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US3258358A (en) * | 1964-04-10 | 1966-06-28 | Millmaster Onyx Corp | Process for producing an antistatic finish on hydrophobic materials |
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US3380881A (en) * | 1961-08-21 | 1968-04-30 | Union Carbide Corp | Curable compositions comprising a polyepoxide and a glycol polyamine |
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US3273956A (en) * | 1961-08-19 | 1966-09-20 | American Cyanamid Co | Method of treating acrylonitrile synthetic fibers |
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US3213053A (en) * | 1962-02-23 | 1965-10-19 | Du Pont | Antistatic composition and treatment of synthetic linear polymer texiles therewith |
AT252177B (de) * | 1962-10-29 | 1967-02-10 | Bunzl & Biach Ag | Verfahren zum Verfestigen von Faservliesen |
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DE1237057C2 (de) * | 1964-03-31 | 1974-03-07 | Verfahren zur herstellung von verfestigten bindemittelfreien faservliesstoffen | |
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DE2907623A1 (de) * | 1979-02-27 | 1980-09-04 | Akzo Gmbh | Verfahren zur herstellung von fibrillierten faserstrukturen |
US4260390A (en) * | 1979-12-10 | 1981-04-07 | Armstrong Cork Company | Additive-solvent process to form embossed product |
US4401708A (en) * | 1981-12-07 | 1983-08-30 | Standard Oil Company (Indiana) | Nonwoven fabric and method of bonding same using microwave energy and a polar solvent |
FR2519503B1 (fr) * | 1981-12-31 | 1991-09-06 | Thomson Csf | Transducteurs piezoelectriques polymeres et procede de fabrication |
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DE4100781C1 (de) * | 1991-01-12 | 1992-02-13 | Deutsche Automobilgesellschaft Mbh, 3300 Braunschweig, De | |
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WO2002007550A1 (de) * | 2000-07-24 | 2002-01-31 | Brevitex Etablissement Pour L'exploitation De Brevets Textiles | Gemusterter schal, verfahren und webmaschine zu seiner herstellung |
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US2772248A (en) * | 1953-05-04 | 1956-11-27 | Interchem Corp | Water-soluble epoxy-amine resins |
US2794754A (en) * | 1956-04-30 | 1957-06-04 | Shell Dev | Treatment of textile materials |
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GB501436A (en) * | 1937-05-24 | 1939-02-24 | Wallach Roger | Improvements relating to yarns, threads and cords, and to textile fabrics made therefrom or incorporating them |
GB544820A (en) * | 1940-10-28 | 1942-04-29 | Richard Walter Hardacre | Improvements relating to the production of pattern effects on textile fabrics |
GB574785A (en) * | 1944-02-18 | 1946-01-21 | Richard Walter Hardacre | Production of local delustred effects on nylon fabrics |
GB708753A (en) * | 1950-10-12 | 1954-05-12 | Sayles Finishing Plants Inc | Improvements in nylon plisse and process of making the same |
US2829071A (en) * | 1954-04-26 | 1958-04-01 | Shell Dev | Treatment of wool containing textiles |
US2869973A (en) * | 1954-08-25 | 1959-01-20 | Du Pont | Synthetic paper sheet of chemically bonded synthetic polymer fibers and process of making the same |
US2817602A (en) * | 1956-09-18 | 1957-12-24 | Jr Clay E Pardo | Shrinkproofing of wool with epoxy resins and polyalkyleneimines |
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0
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- 1958-11-17 US US774137A patent/US2982751A/en not_active Expired - Lifetime
- 1958-11-17 US US774138A patent/US3021232A/en not_active Expired - Lifetime
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1959
- 1959-02-24 US US794813A patent/US3053609A/en not_active Expired - Lifetime
- 1959-11-16 BE BE584710D patent/BE584710A/xx unknown
- 1959-11-16 FR FR810279A patent/FR1243990A/fr not_active Expired
- 1959-11-17 GB GB39001/59A patent/GB923645A/en not_active Expired
- 1959-11-17 DE DEP23902A patent/DE1147910B/de active Pending
- 1959-12-21 NL NL246633D patent/NL246633A/xx unknown
- 1959-12-21 DK DK464459AA patent/DK106547C/da active
- 1959-12-22 GB GB43605/59A patent/GB911282A/en not_active Expired
- 1959-12-22 CH CH8221959A patent/CH381193A/de unknown
- 1959-12-23 FR FR814013A patent/FR1260024A/fr not_active Expired
Patent Citations (3)
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US2772248A (en) * | 1953-05-04 | 1956-11-27 | Interchem Corp | Water-soluble epoxy-amine resins |
BE554506A (de) * | 1956-01-25 | |||
US2794754A (en) * | 1956-04-30 | 1957-06-04 | Shell Dev | Treatment of textile materials |
Cited By (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3316185A (en) * | 1960-11-21 | 1967-04-25 | Union Carbide Corp | Curable polyepoxide compositions containing a glycol diamine |
US3230183A (en) * | 1961-07-07 | 1966-01-18 | Onyx Chemical Corp | Addition products of polyamines with polyalkoxy compounds and textiles treated therewith |
US3380881A (en) * | 1961-08-21 | 1968-04-30 | Union Carbide Corp | Curable compositions comprising a polyepoxide and a glycol polyamine |
US3306809A (en) * | 1961-08-21 | 1967-02-28 | Union Carbide Corp | Curable polyepoxide and glycol polyamine compositions |
US3299169A (en) * | 1961-09-18 | 1967-01-17 | Dow Chemical Co | Elastomeric epoxy resin |
DE1187583B (de) * | 1962-07-03 | 1965-02-25 | Bayer Ag | Mittel zur Verhuetung der elektrostatischen Aufladung geformter Gebilde |
US3242117A (en) * | 1963-10-07 | 1966-03-22 | Millmaster Onyx Corp | Composition and process for producing polyester textile materials having water repellent and antistatic properties |
US3258358A (en) * | 1964-04-10 | 1966-06-28 | Millmaster Onyx Corp | Process for producing an antistatic finish on hydrophobic materials |
US3335105A (en) * | 1964-07-06 | 1967-08-08 | Monsanto Co | Antistatic composition comprising the reaction product of a polyepoxide, a polyamine, and a nitrogen containing compound |
US3399079A (en) * | 1964-09-25 | 1968-08-27 | American Cyanamid Co | Antistatic fiber blend |
US3536646A (en) * | 1967-03-13 | 1970-10-27 | Dow Chemical Co | Method for polymer dilution |
US3462393A (en) * | 1967-05-05 | 1969-08-19 | Dow Chemical Co | Epoxy resin with diamine of polyoxypropylene glycol and method of cure |
US20060162090A1 (en) * | 2002-11-05 | 2006-07-27 | Offord David A | Odor-absorbing cellulosic fibrous substrates |
US20090092572A1 (en) * | 2007-10-01 | 2009-04-09 | Nano-Tex, Inc. | Modification of cellulosic substrates to control body odor |
US8778321B2 (en) | 2007-10-01 | 2014-07-15 | Nanotex Llc | Modification of cellulosic substrates to control body odor |
Also Published As
Publication number | Publication date |
---|---|
CH381193A (de) | 1964-08-31 |
BE584710A (de) | 1960-05-16 |
FR1260024A (fr) | 1961-05-05 |
DK106547C (da) | 1967-02-20 |
FR1243990A (fr) | 1961-01-18 |
GB923645A (en) | 1963-04-18 |
US3053609A (en) | 1962-09-11 |
NL246633A (de) | 1964-02-10 |
DE1147910B (de) | 1963-05-02 |
NL245471A (de) | 1900-01-01 |
US3021232A (en) | 1962-02-13 |
CH8221959A4 (de) | 1964-04-15 |
GB911282A (en) | 1962-11-21 |
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