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 PDF

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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
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Prior art keywords
parts
fabric
composition
polyamine
antistatic
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US774137A
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Harrison I Anthes
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EIDP Inc
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EI Du Pont de Nemours and Co
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Priority to NL245471D priority Critical patent/NL245471A/xx
Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Priority to US774137A priority patent/US2982751A/en
Priority to US774138A priority patent/US3021232A/en
Priority to US794813A priority patent/US3053609A/en
Priority to FR810279A priority patent/FR1243990A/fr
Priority to BE584710D priority patent/BE584710A/xx
Priority to GB39001/59A priority patent/GB923645A/en
Priority to DEP23902A priority patent/DE1147910B/de
Priority to DK464459AA priority patent/DK106547C/da
Priority to NL246633D priority patent/NL246633A/xx
Priority to CH8221959A priority patent/CH381193A/de
Priority to GB43605/59A priority patent/GB911282A/en
Priority to FR814013A priority patent/FR1260024A/fr
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    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01GHORTICULTURE; CULTIVATION OF VEGETABLES, FLOWERS, RICE, FRUIT, VINES, HOPS OR SEAWEED; FORESTRY; WATERING
    • A01G9/00Cultivation in receptacles, forcing-frames or greenhouses; Edging for beds, lawn or the like
    • A01G9/24Devices or systems for heating, ventilating, regulating temperature, illuminating, or watering, in greenhouses, forcing-frames, or the like
    • A01G9/241Arrangement of opening or closing systems for windows and ventilation panels
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/04Coating
    • C08J7/0427Coating with only one layer of a composition containing a polymer binder
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/08Heat treatment
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00Compositions of epoxy resins; Compositions of derivatives of epoxy resins
    • DTEXTILES; PAPER
    • D04BRAIDING; LACE-MAKING; KNITTING; TRIMMINGS; NON-WOVEN FABRICS
    • D04HMAKING 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
    • D04H1/00Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres
    • D04H1/40Non-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
    • D04H1/54Non-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
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322Treating 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
    • D06M13/372Treating 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
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322Treating 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
    • D06M13/385Treating 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
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/55Epoxy resins
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M23/00Treatment of fibres, threads, yarns, fabrics or fibrous goods made from such materials, characterised by the process
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M23/00Treatment of fibres, threads, yarns, fabrics or fibrous goods made from such materials, characterised by the process
    • D06M23/06Processes in which the treating agent is dispersed in a gas, e.g. aerosols
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2323/00Characterised by the use of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Derivatives of such polymers
    • C08J2323/02Characterised 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
    • C08J2323/04Homopolymers or copolymers of ethene
    • C08J2323/06Polyethene
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08JWORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2477/00Characterised by the use of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Derivatives of such polymers
    • YGENERAL 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
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02ATECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A40/00Adaptation technologies in agriculture, forestry, livestock or agroalimentary production
    • Y02A40/10Adaptation technologies in agriculture, forestry, livestock or agroalimentary production in agriculture
    • Y02A40/25Greenhouse technology, e.g. cooling systems therefor
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/04Polyester fibers
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/09Polyolefin
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/10Polyvinyl halide esters or alcohol fiber modification
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/21Nylon
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00Stock material or miscellaneous articles
    • Y10T428/29Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2913Rod, strand, filament or fiber
    • Y10T428/2915Rod, strand, filament or fiber including textile, cloth or fabric
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00Stock material or miscellaneous articles
    • Y10T428/29Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2913Rod, strand, filament or fiber
    • Y10T428/2933Coated or with bond, impregnation or core
    • Y10T428/2964Artificial fiber or filament
    • Y10T428/2967Synthetic resin or polymer
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00Stock material or miscellaneous articles
    • Y10T428/29Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2913Rod, strand, filament or fiber
    • Y10T428/2933Coated or with bond, impregnation or core
    • Y10T428/2964Artificial fiber or filament
    • Y10T428/2967Synthetic resin or polymer
    • Y10T428/2969Polyamide, 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)
  • Polymers & Plastics (AREA)
  • Medicinal Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
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US774137A 1958-11-17 1958-11-17 Process and composition for rendering synthetic hydrophobic material antistatic and the product obtained therefrom Expired - Lifetime US2982751A (en)

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Application Number Priority Date Filing Date Title
NL245471D NL245471A (xx) 1958-11-17
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
US794813A US3053609A (en) 1958-11-17 1959-02-24 Textile
BE584710D BE584710A (xx) 1958-11-17 1959-11-16
FR810279A FR1243990A (fr) 1958-11-17 1959-11-16 Compositions antistatiques, notamment pour matières et articles hydrophobes
GB39001/59A GB923645A (en) 1958-11-17 1959-11-17 Antistatic compositions for hydrophobic shaped structures
DEP23902A DE1147910B (de) 1958-11-17 1959-11-17 Verfahren zur Verringerung der Ansammlung elektrostatischer Ladungen auf hydrophoben Stoffen
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 (xx) 1958-11-17 1959-12-21
CH8221959A CH381193A (de) 1958-11-17 1959-12-22 Verfahren zur Verfestigung von Textilien und einphasige Lösung zur Durchführung dieses Verfahrens
GB43605/59A GB911282A (en) 1958-11-17 1959-12-22 Processes for the treatment of fibrous materials
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

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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

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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

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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

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US (3) US2982751A (xx)
BE (1) BE584710A (xx)
CH (1) CH381193A (xx)
DE (1) DE1147910B (xx)
DK (1) DK106547C (xx)
FR (2) FR1243990A (xx)
GB (2) GB923645A (xx)
NL (2) NL246633A (xx)

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DE1187583B (de) * 1962-07-03 1965-02-25 Bayer Ag Mittel zur Verhuetung der elektrostatischen Aufladung geformter Gebilde
US3230183A (en) * 1961-07-07 1966-01-18 Onyx Chemical Corp Addition products of polyamines with polyalkoxy compounds and textiles treated therewith
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
US3299169A (en) * 1961-09-18 1967-01-17 Dow Chemical Co Elastomeric epoxy resin
US3306809A (en) * 1961-08-21 1967-02-28 Union Carbide Corp Curable polyepoxide and glycol polyamine compositions
US3316185A (en) * 1960-11-21 1967-04-25 Union Carbide Corp Curable polyepoxide compositions containing a glycol diamine
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
US3380881A (en) * 1961-08-21 1968-04-30 Union Carbide Corp Curable compositions comprising a polyepoxide and a glycol polyamine
US3399079A (en) * 1964-09-25 1968-08-27 American Cyanamid Co Antistatic fiber blend
US3462393A (en) * 1967-05-05 1969-08-19 Dow Chemical Co Epoxy resin with diamine of polyoxypropylene glycol and method of cure
US3536646A (en) * 1967-03-13 1970-10-27 Dow Chemical Co Method for polymer dilution
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

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CA690538A (en) * 1959-01-16 1964-07-14 Bohme Fettchemie Gmbh Process for the production and use of water soluble hardenable polyalkylene and/or polyamine condensation products containing epoxide and/or halogen hydrin groups in the molecule
US3115693A (en) * 1959-05-11 1963-12-31 Du Pont Process of making a knitted fabric
US3236586A (en) * 1959-10-09 1966-02-22 Du Pont Process of solvent bonding napped textile fabric
US3273956A (en) * 1961-08-19 1966-09-20 American Cyanamid Co Method of treating acrylonitrile synthetic fibers
BE624231A (xx) * 1961-11-02
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
BE634185A (xx) * 1963-04-11
US3291561A (en) * 1963-04-17 1966-12-13 Du Pont Process of solvent bonding polyethylene terephthalate copolyester fabrics with dimethyl sulfoxide
US3365354A (en) * 1963-08-07 1968-01-23 Johnson & Johnson Overlay sheet and process for making the same
US3313796A (en) * 1964-02-24 1967-04-11 Monsanto Co Process for improving the antistatic properties of synthetic articles
DE1237057C2 (de) * 1964-03-31 1974-03-07 Verfahren zur herstellung von verfestigten bindemittelfreien faservliesstoffen
US3342664A (en) * 1964-06-15 1967-09-19 Monsanto Co Apparatus for producing nonwoven fabric
GB1114922A (en) * 1964-06-17 1968-05-22 Mini Of Technology Manufacture of mouldings from acrylonitrile copolymers
US3484186A (en) * 1964-09-21 1969-12-16 Kanebo Ltd Composition and method for treating textile products of polyamides
GB1120781A (en) * 1964-09-25 1968-07-24 Kurashiki Rayon Kk Method of manufacturing flexible fibrous sheet materials
US3275588A (en) * 1965-06-16 1966-09-27 Dow Chemical Co Ethylenimine-polyalkylenepolyamine-polyepihalohydrin terpolymer flocculants
US3357878A (en) * 1965-10-05 1967-12-12 Kendall & Co Autogenously-bonded needled nonwoven fabric and method of making same
US3489643A (en) * 1966-04-18 1970-01-13 Dexter Corp Sheet material of improved tear strength including long undrawn polyamide fibers
US3653806A (en) * 1966-12-15 1972-04-04 Asahi Chemical Ind Treatment of polyamide fibrous material with titanium trichloride
US3505000A (en) * 1967-01-03 1970-04-07 Nagase & Co Ltd Process for impressing embossed seersucker on crepe design or pattern on knitted fabrics of polyvinyl alcohol fibers
US3530214A (en) * 1967-02-24 1970-09-22 Julius Hermes Method for treating textile materials to uniformly set their shape
US3471319A (en) * 1968-07-22 1969-10-07 Millmaster Onyx Corp Method of imparting to hydrophobic textile materials antistatic properties
US3525653A (en) * 1969-08-13 1970-08-25 Ici Ltd Reduction of pilling of fabrics with ultrasonic energy
US3830683A (en) * 1970-06-30 1974-08-20 Armstrong Cork Co Steam-etched solvent embossed tufted carpet
US3961107A (en) * 1970-10-30 1976-06-01 Hammer Klaus Dieter Fiber fleece containing a polymeric reinforcing material, and process for the production of such fleece
US4500319A (en) * 1979-02-26 1985-02-19 Congoleum Corporation Textured pile fabrics
US4256524A (en) * 1976-11-26 1981-03-17 Monsanto Company Process for solvent bonding blended nonwoven fabrics and fabric produced therefrom
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
US4494285A (en) * 1982-08-16 1985-01-22 Windsor Medical, Inc. Method of making a member defining a lumen for a peristaltic pump and member produced by said method
US4594176A (en) * 1984-04-25 1986-06-10 Economics Laboratory, Inc. Polyalkylene polyamine-glycol accelerators for paint removal compositions
US4537705A (en) * 1984-04-25 1985-08-27 Economics Laboratory, Inc. Aqueous alkaline polyamine paint stripping compositions
US4683080A (en) * 1984-06-11 1987-07-28 Morton Thiokol, Inc. Microbiocidal compositions comprising an aryl alkanol and a microbiocidal compound dissolved therein
US4663077A (en) * 1984-06-11 1987-05-05 Morton Thiokol Inc. Microbiocidal compositions comprising an aryl alkanol and a microbiocidal compound dissolved therein
US4661275A (en) * 1985-07-29 1987-04-28 The Lubrizol Corporation Water-based functional fluid thickening combinations of surfactants and hydrocarbyl-substituted succinic acid and/or anhydride/amine terminated poly(oxyalkylene) reaction products
US4664834A (en) * 1985-07-29 1987-05-12 The Lubrizol Corporation Hydrocarbyl-substituted succinic acid and/or anhydride/amine terminated poly(oxyalkylene) reaction products, and aqueous systems containing same
US4686140A (en) * 1985-11-29 1987-08-11 The United States Of America As Represented By The Secretary Of The Agriculture Wood veneer panels bonded with cellulose solvents
US4755311A (en) 1986-08-14 1988-07-05 The Lubrizol Corporation Phosphorus-, sulfur- and boron-containing compositions, and lubricant and functional fluid compositions containing same
EP0453624B1 (en) * 1990-04-25 1999-01-13 Descente Ltd. Highly moisture-absorptive fiber
DE4100781C1 (xx) * 1991-01-12 1992-02-13 Deutsche Automobilgesellschaft Mbh, 3300 Braunschweig, De
WO1996027703A1 (en) * 1995-03-06 1996-09-12 Weyerhaeuser Company Fibrous web having improved strength and method of making the same
EP1303200B1 (de) * 2000-07-24 2005-10-19 Brevitex Etablissement pour l'exploitation de brevets textiles Gemusterter schal, verfahren und webmaschine zu seiner herstellung

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GB574785A (en) * 1944-02-18 1946-01-21 Richard Walter Hardacre Production of local delustred effects on nylon fabrics
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Cited By (15)

* Cited by examiner, † Cited by third party
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
BE584710A (xx) 1960-05-16
GB923645A (en) 1963-04-18
DE1147910B (de) 1963-05-02
CH8221959A4 (xx) 1964-04-15
DK106547C (da) 1967-02-20
NL246633A (xx) 1964-02-10
NL245471A (xx) 1900-01-01
FR1260024A (fr) 1961-05-05
US3021232A (en) 1962-02-13
CH381193A (de) 1964-08-31
US3053609A (en) 1962-09-11
FR1243990A (fr) 1961-01-18
GB911282A (en) 1962-11-21

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