US3021232A - Process for rendering synthetic hydrophobic material antistatic and the product obtained therefrom - Google Patents

Process for rendering synthetic hydrophobic material antistatic and the product obtained therefrom Download PDF

Info

Publication number
US3021232A
US3021232A US774138A US77413858A US3021232A US 3021232 A US3021232 A US 3021232A US 774138 A US774138 A US 774138A US 77413858 A US77413858 A US 77413858A US 3021232 A US3021232 A US 3021232A
Authority
US
United States
Prior art keywords
parts
fabric
polyamine
log
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
Application number
US774138A
Other languages
English (en)
Inventor
Pretka John Edward
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
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 US774138A priority patent/US3021232A/en
Priority to US774137A priority patent/US2982751A/en
Priority to US794813A priority patent/US3053609A/en
Priority to BE584710D priority patent/BE584710A/xx
Priority to FR810279A priority patent/FR1243990A/fr
Priority to GB39001/59A priority patent/GB923645A/en
Priority to DEP23902A priority patent/DE1147910B/de
Priority to NL246633D priority patent/NL246633A/xx
Priority to DK464459AA priority patent/DK106547C/da
Priority to GB43605/59A priority patent/GB911282A/en
Priority to CH8221959A priority patent/CH381193A/de
Priority to FR814013A priority patent/FR1260024A/fr
Application granted granted Critical
Publication of US3021232A publication Critical patent/US3021232A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • 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 of matter. More particularly it is concerned with a synthetic, hydrophobic sphaped structure bearing a novel finish to minimize the accumulation of charges of static electricity during finishing operations and normal use.
  • antistatic agents usefulin the textile arts lack durability and some impart to textiles undesirable properties such as unpleasant hand and discoloration upon application or with continued fabric use. Furthermore, some known antistatic agents are operable only within a narrow pH range and thus lack compatibility with many 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.
  • a synthetic, hydrophobic shaped structure which minimizes accumulation of charges of static electricity is provided by epoxide curing at a pH below 7.0 in the presence of an epoxide curing catalyst a synthetic hydrophobic shaped structure bearing a polyamine of the formula:
  • Atent R Since the nature of atent R is not critical provided it is inert to reaction with amines, it may be any member of the class consisting of o o 0 H H 0 g H H I I ll and A- wherein -A-- is a member of the class consisting of divalent aliphatic, alicyclic, aromatic and heterocyclic radicals. Preferably A- is hydrocarbon.
  • a particularly desirable class of polyamines are those of the formula: I
  • X is a member of the class consisting of wherein -R' is a member of the class consisting of hydrogen, lower alkyl (i.e., an alkyl radical containing less than about 8 carbon atoms in its longest chain) and amino lower alkyl and -Y- is divalent aliphatic which while it may contain aza linkages is otherwise hydrocarbon, q being a number from about 6 to about 40.
  • -R' is a member of the class consisting of hydrogen, lower alkyl (i.e., an alkyl radical containing less than about 8 carbon atoms in its longest chain) and amino lower alkyl and -Y- is divalent aliphatic which while it may contain aza linkages is otherwise hydrocarbon, q being a number from about 6 to about 40.
  • the preparation of these polyamines is discussed in detail in Belgian Patents 554,506, granted January 25, 1957, and 560,446, granted September 14, 1957.
  • the polyethylene glycol dihalide e.g.
  • chloride, bromide or iodide) analogue is condensed (with release of hydrogen halide) with an amine, the nitrogen of which contains at least two active hydrogen.
  • amines methylamine, ethylamine, propylamine, butylamine, amylamine, hexylamine, dodecylamine, alylamine, monoethanolamine, 3-isopropyl-n-propylamine, 3-methoxy-npropylamine, diethylenetriamine, bis(3-aminopropyl) amine, bis(2-aminopropyl)amine, hexamethylene diamine, triethylene tetramine, tetraethylene pentamine and the like.
  • epoxide curing is meant that the polyamine defined above is reacted, after application of the reactants to the said shaped structure, with a polyepoxide.
  • a polyepoxide 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.
  • Such a material with a molecular weight of between about 280 to 360 is available on the open market under the trademark Eponite 100 (viscosity -150 cp. at 25 C.; 10.2 lbs./ gal.) by the Shell Chemical Corp.
  • Eponresins which are diepoxide condensation products of epichlorohydrin and dimethyl, di-para hydroxyphenyl methane and the poly(allyl glycidyl ethers).
  • a typical siloxane is l,3-bis- [-3-(2,3-epoxy propoxy) propyl] tetramethyldisiloxane sold under the trade mark Syl-Kern 90 by Dow Corning Corp., Midland, Michigan.
  • Reaction of the polyamine (I) or (II) with the polyepoxide' may be conveniently accomplished by heating the shaped structure to which an and 30 parts by volume perchloroethylene 2.1 parts by volume dry cleaning soap (sold by R. R. Street 8; Co., Inc., 569 W. Monroe Street, Chicago,
  • the bleaching procedure representative of prevailing commercial practice, consists of immersing fabric in 100 times its weight of bleaching bath containing:
  • Durability of antistatic treatments ing, and dry cleaning is determined by measurement of surface resistances of the fabrics. These measurements are made under controlled conditions of 25% relative humidity and a temperature of 70 F. Current flowing across, the fabric is measured accurately with a Beckman, Model V Micro-microammeter, and the surface resistnee is then calculated from this and the known applied voltage. For convenience, these values are reported as logarithms of surface resistance. In general, the lower the surface resistance, the lower is the tendency of the fabric to develop a static charge. Surface reflectance of undyed fabrics is used as a measure of whiteness. Measurements are made using a Photovolt Model 610 and steam pressing. to bleaching, washreflectometer. By using green, amber, and blue filters, grayness and yellowness can be estimated.
  • EXAMPLE 1 100 parts of the polyamine formed by condensation of diethylene triamine with the dichloride of polyethylene glycol having a molecular weight of 600 (Aston L as identified above) as a 20% solids solution in water is stirred into 5000 parts of water. The pH of the resulting solution is adjusted to 3.2 by addition of 70 parts of a solution of hydrochloric acid in water. 62 parts of Eponite as identified above is then added and the mixture is dispersed using a Waring Blender. While mixing in the Waring Blender, 4 parts of zinc fluoroborate catalyst as a 40% aqueous solution is added. A slightly turbid solution 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 160 C. and thereafter scoured for 15 minutes at F.
  • the fabric is observed to have gained 3.2% by weight of antistatic finish based on the original Weight of the fabric.
  • the treated fabric has a log R of 10.3 compared with an original log R of 14.2. After the standard bleaching the sample is observed to have a log R of 12.9.
  • a 21% by weight finish based on the Weight of the fabric is attained when 1240 parts of Eponite 100 is employed 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 bleachmg.
  • Example 1 is modified by employing as the polyamine component the reaction product of the dichloride of polyethylene glycol having a molecular weight of 600 with methylamine (Aston 108 as identified above). The percent by weight of finish picked up by the fabric samples as Well as log Rs before and after standard bleaching when using 62 parts of the diepoxide (A) and when using 1240 parts of the diepoxide (B) are shown in Table 1.
  • Sample (B) is found to be waxy and stiff.
  • a Waring Blender is employed to mix 500 parts of Aston 108 as a 20% solids solution in water, 100 parts of a 10% aqueous solution of hydrochloric acid, 62 parts of Eponite 100 and 4 parts of zinc fluoroborate catalyst as a 40% aqueous solution. The pH of the resulting mixture is 3.5. The mixture is then stirred into 4340 parts of water. The finish is padded upon four fabric swatches identified in Table II.
  • the finish is applied using a laboratory padder set at 50 lbs. per square inch providing t-wo dips and two nips. After padding all fabric samples are dried overnight at room temperature and thereafter cured for 6 minutes at C.
  • the initial log R of the samples, the percent by weight of antistatic agent deposited based on the weight of the fabric and the log R observations before and after washing, bleaching and dry cleaning are shown in Table III.
  • the samples treated with the finish cross-linked with the diiodide are labeled C D and E.
  • the table shows a comparative figure of yellowness factor relative to samples C and C D and D These compare to the yellowness factor of the untreated controls of 2.02 and 5.8 respectively.
  • Samples of a tow of continuous filaments formed from a polymer of acryolnitrile (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.
  • washing tests are carried out with 0.1% aqueous Tide using a 15-minute wash cycle at 60 C. followed by two 5 minute rinses at 60 C.
  • a cationic blue tint when added to the compositions employed in treating samples H, I and J results in reduction of the color of the samples to less than that of the control.
  • optical whiteners and silicone water proofing agents and other commonly used textile treating agents may be simultaneously applied with the antistatic agents of the present invention to perform their conventional roles.
  • EXAMPLE 5 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 prepared by mixing 15 parts of sodium styrene sulfonate, parts of diionized water, 0.15 part of glyceryl monooleate, .08 part of alkyl phenoxy polyoxyethanol and 1.67 parts of glycidyl methacryate in a Waring Blendor to form an emulsion.
  • the emulsion is added to a 200 ml. 3-necked flask which is then flushed with nitrogen. .06 part of a,u-azobisisobutyryl nitrile is then added and the reaction mass is lheated for 3 hours at 70 C. A thick semi-transparent 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 polyepoxide resin in a 1:1 weight ratio.
  • Aston 108 is employed as the polyamine in each application.
  • 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.
  • the identity of the polyepoxide curing agent employed in each example is identified in Table VII.
  • the color and log R of each sample after curing is reported in Table VIII.
  • Eponite 100 Epon 815. Poly allyl glycidyl other.
  • EXAMPLE 8 A mixture of 50 parts of Aston 108 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. Orion 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.
  • hydrophobic shaped structure is meant a structure such as a foam, fiber, filament, yarn, staple, fabric, pellicle and the like, produced from a synthetic polymeric material, having a moisture regain of no greater than 5%, such as a polyamide, a polymer produced from acrylonitrile, a polyester, or the like.
  • Suitable polyamides are those produced from a linear polymer containing recurring units of the formula:
  • Z is a member of the class consisting of a divalent hydrocarbon radical and a divalent radical of the formula ethylenically unsaturated compounds which are suitable 75 as the minor constituent in forming useful copolymers with acrylonitn'le are listed in United States Patents Nos. 2,837,501; 2,486,241 and 2,436,926.
  • polyesters from which such structures may be devised include polyethylene terephthalate, polyethylene terephthalate copolyesters prepared using polyethylene glycols such as polyethylene glycols 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 glycols 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.
  • Application of the antistatic finish of the present invention 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% may be 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 pickup 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 polyamine:polyepoxide is maintained within the limits of 10:3 to 10:7.
  • Higher ratios of polyepoxide such as 1:'l 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 applied 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 reacted 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 efiicient drying of the textile. Usually temperature adiustment 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 at curing cycle of about 10 minutes at 270 F. is adequate.
  • a process of minimizing the accumulation of charge of static electricity upon a synthetic, hydrophobic shaped structure which comprises applying to the said structure at a pH below 7.0 and in the presence of an epoxide curing catalyst, a mixture of a polyepoxide and a polyamine of the formula:
  • R is an organic divalent radical
  • -X is a member of the class consisting of amino nitrogen and divalent radical terminating in amino nitrogen
  • m and n are small whole numbers from about 3 to about 40 and p is an integer no greater than about and thereafter reacting the said polyepoxide and the said polyamine together.
  • a process of minimizing the accumulation of charge of static electricity upon a synthetic, hydrophobic shaped structure which comprises applying to the said structure at a pH below 7.0 and in the presence of an epoxide curing catalyst, a mixture of a polyepoxide and polyamine of the formula:
  • q is a number from about 6 to about 40 and p is an integer no greater than about 10 10 and thereafter reacting the said polyepoxide and the said polyamine together.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Organic Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Environmental Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Thermal Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
US774138A 1958-11-17 1958-11-17 Process for rendering synthetic hydrophobic material antistatic and the product obtained therefrom Expired - Lifetime US3021232A (en)

Priority Applications (13)

Application Number Priority Date Filing Date Title
NL245471D NL245471A (fr) 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
FR810279A FR1243990A (fr) 1958-11-17 1959-11-16 Compositions antistatiques, notamment pour matières et articles hydrophobes
BE584710D BE584710A (fr) 1958-11-17 1959-11-16
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
NL246633D NL246633A (fr) 1958-11-17 1959-12-21
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.
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
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
US78241258A 1958-12-23 1958-12-23
US794813A US3053609A (en) 1958-11-17 1959-02-24 Textile

Publications (1)

Publication Number Publication Date
US3021232A true US3021232A (en) 1962-02-13

Family

ID=27505730

Family Applications (3)

Application Number Title Priority Date Filing Date
US774138A Expired - Lifetime US3021232A (en) 1958-11-17 1958-11-17 Process for rendering synthetic hydrophobic material antistatic and the product obtained therefrom
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
US794813A Expired - Lifetime US3053609A (en) 1958-11-17 1959-02-24 Textile

Family Applications After (2)

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
US794813A Expired - Lifetime US3053609A (en) 1958-11-17 1959-02-24 Textile

Country Status (8)

Country Link
US (3) US3021232A (fr)
BE (1) BE584710A (fr)
CH (1) CH381193A (fr)
DE (1) DE1147910B (fr)
DK (1) DK106547C (fr)
FR (2) FR1243990A (fr)
GB (2) GB923645A (fr)
NL (2) NL246633A (fr)

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1187583B (de) * 1962-07-03 1965-02-25 Bayer Ag Mittel zur Verhuetung der elektrostatischen Aufladung geformter Gebilde
US3213053A (en) * 1962-02-23 1965-10-19 Du Pont Antistatic composition and treatment of synthetic linear polymer texiles therewith
US3230183A (en) * 1961-07-07 1966-01-18 Onyx Chemical Corp Addition products of polyamines with polyalkoxy compounds and textiles treated therewith
US3258358A (en) * 1964-04-10 1966-06-28 Millmaster Onyx Corp Process for producing an antistatic finish on hydrophobic materials
US3275588A (en) * 1965-06-16 1966-09-27 Dow Chemical Co Ethylenimine-polyalkylenepolyamine-polyepihalohydrin terpolymer flocculants
US3313796A (en) * 1964-02-24 1967-04-11 Monsanto Co Process for improving the antistatic properties of synthetic articles
US3347803A (en) * 1959-01-16 1967-10-17 Bohme Fettchemie Gmbh Process for the production of hardenable synthetic resinous products containing halohydrin groups
US3471319A (en) * 1968-07-22 1969-10-07 Millmaster Onyx Corp Method of imparting to hydrophobic textile materials antistatic properties
US4537705A (en) * 1984-04-25 1985-08-27 Economics Laboratory, Inc. Aqueous alkaline polyamine paint stripping compositions
US4594176A (en) * 1984-04-25 1986-06-10 Economics Laboratory, Inc. Polyalkylene polyamine-glycol accelerators for paint removal compositions
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
WO1988001272A2 (fr) 1986-08-14 1988-02-25 The Lubrizol Corporation Sels d'amines de borate d'acides monothiophosphoriques
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

Families Citing this family (44)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
US3316185A (en) * 1960-11-21 1967-04-25 Union Carbide Corp Curable polyepoxide compositions containing a glycol diamine
US3273956A (en) * 1961-08-19 1966-09-20 American Cyanamid Co Method of treating acrylonitrile synthetic fibers
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
NL135829C (fr) * 1961-11-02
AT252177B (de) * 1962-10-29 1967-02-10 Bunzl & Biach Ag Verfahren zum Verfestigen von Faservliesen
BE634185A (fr) * 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
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
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
US3395107A (en) * 1964-07-06 1968-07-30 Burnthall Edward Vernon Antistatic composition for synthetic fibers
US3484186A (en) * 1964-09-21 1969-12-16 Kanebo Ltd Composition and method for treating textile products of polyamides
US3399079A (en) * 1964-09-25 1968-08-27 American Cyanamid Co Antistatic fiber blend
GB1120781A (en) * 1964-09-25 1968-07-24 Kurashiki Rayon Kk Method of manufacturing flexible fibrous sheet materials
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
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
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
US4663077A (en) * 1984-06-11 1987-05-05 Morton Thiokol Inc. Microbiocidal compositions comprising an aryl alkanol and a microbiocidal compound dissolved therein
US4683080A (en) * 1984-06-11 1987-07-28 Morton Thiokol, Inc. Microbiocidal compositions comprising an aryl alkanol and a microbiocidal compound dissolved therein
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
DE69032895T2 (de) * 1990-04-25 1999-05-27 Descente Ltd Faser mit hoher Feuchtigkeitsabsorption
DE4100781C1 (fr) * 1991-01-12 1992-02-13 Deutsche Automobilgesellschaft Mbh, 3300 Braunschweig, De
WO1996027703A1 (fr) * 1995-03-06 1996-09-12 Weyerhaeuser Company Bande fibreuse a solidite amelioree et son procede de production
RU2247521C2 (ru) * 2000-07-24 2005-03-10 Бревитекс Этаблиссман Пур Л`Эксплутасьон Де-Бревет Текстиль Шарф с рисунком, способ и ткацкая машина для изготовления такого шарфа

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE554506A (fr) * 1956-01-25
US2794754A (en) * 1956-04-30 1957-06-04 Shell Dev Treatment of textile materials

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
US2772248A (en) * 1953-05-04 1956-11-27 Interchem Corp Water-soluble epoxy-amine resins
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

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE554506A (fr) * 1956-01-25
US2794754A (en) * 1956-04-30 1957-06-04 Shell Dev Treatment of textile materials

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3347803A (en) * 1959-01-16 1967-10-17 Bohme Fettchemie Gmbh Process for the production of hardenable synthetic resinous products containing halohydrin groups
US3230183A (en) * 1961-07-07 1966-01-18 Onyx Chemical Corp Addition products of polyamines with polyalkoxy compounds and textiles treated therewith
US3213053A (en) * 1962-02-23 1965-10-19 Du Pont Antistatic composition and treatment of synthetic linear polymer texiles therewith
DE1187583B (de) * 1962-07-03 1965-02-25 Bayer Ag Mittel zur Verhuetung der elektrostatischen Aufladung geformter Gebilde
US3313796A (en) * 1964-02-24 1967-04-11 Monsanto Co Process for improving the antistatic properties of synthetic articles
US3258358A (en) * 1964-04-10 1966-06-28 Millmaster Onyx Corp Process for producing an antistatic finish on hydrophobic materials
US3275588A (en) * 1965-06-16 1966-09-27 Dow Chemical Co Ethylenimine-polyalkylenepolyamine-polyepihalohydrin terpolymer flocculants
US3471319A (en) * 1968-07-22 1969-10-07 Millmaster Onyx Corp Method of imparting to hydrophobic textile materials antistatic properties
US4537705A (en) * 1984-04-25 1985-08-27 Economics Laboratory, Inc. Aqueous alkaline polyamine paint stripping compositions
US4594176A (en) * 1984-04-25 1986-06-10 Economics Laboratory, Inc. Polyalkylene polyamine-glycol accelerators for paint removal compositions
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
WO1988001272A2 (fr) 1986-08-14 1988-02-25 The Lubrizol Corporation Sels d'amines de borate d'acides monothiophosphoriques
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
NL246633A (fr) 1964-02-10
FR1243990A (fr) 1961-01-18
DE1147910B (de) 1963-05-02
US2982751A (en) 1961-05-02
FR1260024A (fr) 1961-05-05
GB923645A (en) 1963-04-18
CH381193A (de) 1964-08-31
DK106547C (da) 1967-02-20
BE584710A (fr) 1960-05-16
CH8221959A4 (fr) 1964-04-15
GB911282A (en) 1962-11-21
US3053609A (en) 1962-09-11
NL245471A (fr) 1900-01-01

Similar Documents

Publication Publication Date Title
US3021232A (en) Process for rendering synthetic hydrophobic material antistatic and the product obtained therefrom
US2403960A (en) Antistatic treatment of vinyl resin articles
US2897170A (en) Antistatic treatment with a quaternary ammonium compound containing a polyetheneoxy grouping and products thereof
EP0315477B1 (fr) Méthode pour le traitement de la laine
US3382096A (en) Antistatic composition, treatment of a hydrophobic material therewith, and the resulting material
US3475207A (en) Fabrics having improved tear strength obtained by treatment with high density oxidized polyethylene
Yang et al. Silk fabric non-formaldehyde crease-resistant finishing using citric acid
CN1594716B (zh) 纺织整理方法
US2955961A (en) Process of coating polyethylene terephthalate substrate with a polyurethane and resultant article
EP0372782B1 (fr) Méthode de traitement de fibres cellulosiques
US2723246A (en) Antistatic compositions
US3428480A (en) Flame-retardant cellulosic material,composition and method for making same
EP0394689A2 (fr) Procédé de traitement de textiles et d'autres substrats avec des silicones cationiques aptes à être épuisés
US3051674A (en) Textile finishing composition comprising an aqueous dispersion of the interaction product of urea, formaldehyde, a fatty acid amide and a primary amine
US2729577A (en) Method of imparting antistatic properties to textile materials
US3813220A (en) Process for modifying keratinous material,composition useful therein,and keratinous material bearing thereon said composition
US3738864A (en) Fiber bearing antistatic composition
US5858023A (en) Softening agents
EP1409784B1 (fr) Traitement de textiles avec des polyethers fluores
US2914427A (en) Polymeric amido imidazolines and their alkylation products, and textiles coated therewith
EP0553217B1 (fr) Agents assouplissants
US3736177A (en) Water and oil-resistant,antistatic and abrasion-resistant finish for nylon fabrics
US3230183A (en) Addition products of polyamines with polyalkoxy compounds and textiles treated therewith
US3134686A (en) Durable antistatic finish and process for applying same
US3522195A (en) Process for providing a durable antistatic finish for synthetic textile materials