US3206328A - Process for imparting anti-static properties to hydrophobic textile materials and product thereof - Google Patents

Process for imparting anti-static properties to hydrophobic textile materials and product thereof Download PDF

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Publication number
US3206328A
US3206328A US11973A US1197360A US3206328A US 3206328 A US3206328 A US 3206328A US 11973 A US11973 A US 11973A US 1197360 A US1197360 A US 1197360A US 3206328 A US3206328 A US 3206328A
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Prior art keywords
diglycidyl ether
fabric
textile
acid
treated
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US11973A
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Inventor
John T Shaw
Frank J Gross
William J Van Loo
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Wyeth Holdings LLC
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American Cyanamid Co
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Priority to BE600676D priority Critical patent/BE600676A/xx
Priority to NL261845D priority patent/NL261845A/xx
Application filed by American Cyanamid Co filed Critical American Cyanamid Co
Priority to US11973A priority patent/US3206328A/en
Priority to FR853726A priority patent/FR1281706A/fr
Application granted granted Critical
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    • 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
    • D06M13/35Heterocyclic compounds
    • D06M13/355Heterocyclic compounds having six-membered heterocyclic rings
    • D06M13/358Triazines
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • 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
    • D06M13/10Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
    • D06M13/11Compounds containing epoxy groups or precursors thereof
    • 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
    • D06M13/10Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
    • D06M13/12Aldehydes; Ketones
    • D06M13/127Mono-aldehydes, e.g. formaldehyde; Monoketones
    • 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
    • D06M13/10Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
    • D06M13/144Alcohols; Metal alcoholates
    • 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
    • D06M13/10Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
    • D06M13/184Carboxylic acids; Anhydrides, halides or salts thereof
    • D06M13/192Polycarboxylic acids; Anhydrides, halides or salts thereof
    • 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
    • D06M13/325Amines
    • 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
    • D06M13/325Amines
    • D06M13/335Amines having an amino group bound to a carbon atom of a six-membered aromatic ring
    • 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
    • D06M13/402Amides imides, sulfamic acids
    • D06M13/41Amides derived from unsaturated carboxylic acids, e.g. acrylamide
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/0056Dyeing with polymeric dyes involving building the polymeric dyes on the fibres
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/0056Dyeing with polymeric dyes involving building the polymeric dyes on the fibres
    • D06P1/0064Dyeing with polymeric dyes involving building the polymeric dyes on the fibres by using reactive polyfunctional compounds, e.g. crosslinkers
    • 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
    • Y10S260/00Chemistry of carbon compounds
    • Y10S260/15Antistatic agents not otherwise provided for
    • Y10S260/19Non-high polymeric antistatic agents/n
    • Y10S260/20Antistatic agent contains pentavalent nitrogen
    • 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
    • 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
    • Y10T428/31504Composite [nonstructural laminate]
    • Y10T428/31511Of epoxy ether
    • 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
    • Y10T442/00Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/20Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
    • Y10T442/2369Coating or impregnation improves elasticity, bendability, resiliency, flexibility, or shape retention of the fabric
    • Y10T442/2385Improves shrink resistance
    • 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
    • Y10T442/00Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/20Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
    • Y10T442/2418Coating or impregnation increases electrical conductivity or anti-static quality
    • Y10T442/2459Nitrogen containing
    • 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
    • Y10T442/00Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/20Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
    • Y10T442/2582Coating or impregnation contains an optical bleach or brightener or functions as an optical bleach or brightener [e.g., it masks fabric yellowing, etc.]

Definitions

  • the present invention relates to novel compositions, processes for durably modifying textile materials and the so modified materials.
  • durable modification is intended to include dyeing, the impartation of an anti-static finish, the impartat-ion of a durable fluorescent or brightening effect, the impartation of shrinkage resistance and animalization of cellulosic substrates and numerous other changes or modifications in suitable substrates.
  • substrate as that term is employed herein, is meant a base material which may either be a formed fabric and preferably, is or may be molded or extruded articles containing or made from hydrophobic synthetic resins.
  • the substrate or base is a formed textile material and may be knitted, woven, non-woven, felted, or otherwise formed.
  • textile material as that term is employed herein, it is meant fibers, filaments, two, or fabrics which, as noted above, may be Woven, non-woven, knitted felted or otherwise formed, prepared from natural fibers of either vegetable or animal origin, synthetic fibers or combinations and mixtures of natural and synthetic fibers.
  • natural fibers contemplated are cotton, linen, hemp, ramie, jute and the like, and among the natural fibers of animal origin are Wool, vicuna and the like.
  • synthetic fibers are nylon, viscose rayon, cellulose acetate, polyester fibers and acrylic fibers. It will be noted that the present invention results in imparting durable anti-static properties to fabrics composed of synthetic hydrophobic fibers which are subject to the accumulation of static electricity.
  • Such materials include nylon, the acrylic fibers, polyester fibers and the like.
  • the textile material is preferably cellulosic in origin or contains at least 50% of cellulose fiber, as for example cotton.
  • Still further objects of the present invention relate to novel compositions, methods of employing the same on suitable substrates and the substrates so finished, whereby improved durable dyeing, the impartatio-n of fluorescent brightening, the animalization of the fiber, the impartation of an anti-static finish, and numerous other modifications thereof may be readily and easily accomplished. Often more than one desirable modification is imparted to a substrate in a single finishing step.
  • novel polymeric reaction products are prepared by reacting two diiferent compounds having the following general formulae:
  • R and R are organic nuclei and X and X and Y and Y are functional elements which can react, the Xs and with the Ys.
  • the novel compounds or polymers are preferably formed in situ on the suitable substrate and particularly on textile material. This may be accomplished by way of illustration through the application of a polyfunctional textile agent, together with a second polyfunctional compound.
  • the illustrative textile agent contains two or more groups which can react with two or more groups of the polyfunctional compound to form a polymer in the fibers and/ or on the fibers of the textile material.
  • textile agent is principally a term of convenience in that many of the hereinafter illustrative X-RX polyfunctional compounds are dyes, brighteners, etc., which have known utility in the textile field.
  • R is an organic nucleus of a. homogeneous or heterogeneous organic chain or organic ring compound, as for example of a dye, molecule, anti-static agent, a water or grease repellent, an ultraviolet absorber, a softener, a fire retardant, a bactericide, a moth repellent, a brightener, or other suitable agent which may impart a desirable property to a substrate and in particular, to a textile fiber or fabric.
  • R is the nucleus of a homogeneous or heterogeneous organic chain or organic ring compound.
  • R may be alkyl, aryl, alkaryl and aralkyl.
  • Y and Y may be isothiocyanato (MCS), isocyanato (NCO) or l-aziridinyl CH (I CH2
  • YR --Y may be methylene-bis-acrylamide, (CH CHCONH) CH
  • the preferred polyfunctional textile agents (XRX are those having the following general formulae:
  • Z is a monovalent anion such as halide, and n is or 1, and
  • polyglycidyl ethers dibutyl carbonate, hexamethylene diisocyanate, triethylene melamine, divinyl sulfone, epichlor-ohydrin, 2,4-dichloros-triazine, 2,4,6-trichloro-s-triazine, 2,4-dichloro-6-methyl-s-triazine, 2,4-dichloro-6-butyl-s-triazine, 2,4-dichloro-6-phenyl-s-triazine, 2,4 dichloro o-benzyl-striazine, methylene-bishcrylamide, tetramethylol acetone and triphenyl cyanurate are illustrative compounds.
  • the textile agents and the polyfunctional organic compounds capable of reacting with each other to form the novel reaction products of this invention may be applied to suitable substrates and in particular, textile materials by conventional methods as for example by padding, dipping, spraying, immersion and the like.
  • the two components, i.e., the textile agents as they are classified herein and the polyfunctional compounds, may be applied individually from separate baths or advantageously simultaneously from the same bath.
  • the polyfunctional compounds may be applied in amounts varying over a comparatively wide range of from between .5% to about 25% based on the dry weight of the textile material.
  • the amount may vary from between .5% and 15% based on the dry weight of the fabric.
  • the finish is essentially for purposes of optical brightening or dyeing, the polyfunctional compounds may be employed in amounts of from between .5% and 5% of the fabric. Shrinkage control usually requires between 2% and 20% and so on depending upon the particular finishes to be effected.
  • the textile agent and second polyfunctional compound may be employed in comparatively wide molecular ratio one to the other and still achieve very satisfactory results. Preferably they are employed in approximately equal molar quantities or with an excess of the second polyfunctional compound. As a general rule, they are employed in mole ratios of between about .01 mole to about 1 mole of the textile agent to about 1 mole of the second polyfunctional compound and preferably from between about .1 to about 1 mole of the former to 1 mole of the latter.
  • a suitable alkaline catalyst may be applied separately, with one of the components, or in combination with each of the components and simultaneously therewith as from a single bath.
  • a catalyst may be an alkaline agent, such as alkali metal hydroxide used as sodium, potassium, lithium or ammonium hydroxide or the alkaline earth metal oxides and hydroxides; in addition, tertiary amines and triethyl amine, tributyl amine, dimethyl aniline and the like.
  • alkali metal hydroxide used as sodium, potassium, lithium or ammonium hydroxide or the alkaline earth metal oxides and hydroxides
  • tertiary amines and triethyl amine, tributyl amine, dimethyl aniline and the like in some instances, as when the reactants are definitely basic and a sufiicient alkaline medium is obtained, added catalyst is not required to effect polymerization.
  • polymerization is effected at a pH of between about 8 and about 13.
  • the polyfunctional compounds may be both water soluble and, as will be apparent, for many applications they are preferably so.
  • solvent soluble polyfunctional compounds are fully contemplated as is the use of water soluble and solvent soluble compounds in a single application. Suitable'solvents will readily suggest themselves depending on the application to be effected. Thus, solvents such as benzene, xylene, carbon tetrachloride, acetone and the like may be employed.
  • the polymerization reaction preferably carried out in situ on the substrate to be durably modified, is brought about by the application of heat to the treated fabric.
  • the temperature required for the polymerization is usually from between about 125 F. and about 400 F.
  • the time required to complete the polymerization varies inversely with the temperature used. That is, atthe lower curing temperature, the longer time is required and vice versa.
  • the finishes applied in accordance with the present invention to textile materials have improved durability to washing and particularly to washing under alkaline conditions.
  • Nylon talfeta was treated with the above solutions by padding, obtaining a 50% wet-pickup. After drying at 225 F. for 2 minutes, the fabrics were heated at 300 F. for 3 minutes.
  • the treated fabrics contained the amounts of'4,4-diamino-2,2-stilbenedisulfonic acid shown in the Table I, and 5% of the diglycidyl ether of ethylene glycol on the weight of the fabric.
  • the treated fabrics were treated for their anti-static properties by the cigarette ash test, which may be described as follows: i
  • the treated fabric is exposed to an atmosphere of 40% relative humidity for four hours. Afterbeing stroked rapidly and heavily several times with a glass rod, the
  • the fabric is held close to cigarette ashes. If the ashes do not jump and cling to the fabric, the fabric is considered to have good anti-static properties.
  • Table I demonstrates that the use of an accelerator of the type normally employed with epoxy resins tends to adversely affect the durability of the finish in accordance with this invention. More importantly, Table I demonstrates that outstanding and durable anti-static properties may be imparted to nylon in accordance with the present invention.
  • Nylon taffeta was treated with the above solution by padding, obtaining a wet-pickup. After drying at 225 F. for 2 minutes, the fabric was heated at 300 F. for 3 minutes. The treated fabric contained 5% of each of the above agents on the weight of the fabric.
  • Example 1 The test for anti-static properties and the Washes were carried out as in Example 1. The treated fabric showed good anti-static properties for 7 washes.
  • the treated fabric showed good anti-static properties for 5 washes.
  • EXAMPLE 5 Application of 8-amin0-1-naphthol-5sulfonic acid and diglycidyl ether of ethylene glycol on nylon as an anti-static An aqueous solution was prepared containing 5% of S-amino-l-naphthol-S-sulfonic acid, 20% of sodium hydroxide on the weight of the naphtholsulfonic acid, and 10% of diglycidyl ether of ethylene glycol (pH:11.8).
  • Nylon taffeta was treated with the above solution by padding, obtaining a 50% wet-pickup. After drying at 225 F. for 2 minutes, the fabric was heated at 300 F. for 3 minutes. The treated fabric contained 2.5% of S-amino-l-naphthol-S-sulfonic acid and 5% of the diglycidyl ether of ethylene glycol.
  • Nylon taffeta was treated with the above solution by padding, obtaining a 50% wet-pickup. After drying at 225 F. for 2 minutes, the fabric was heated at 300 F. for 3 minutes. The treated fabric contained 5% of each of the above agents on the weight of the fabric.
  • Example 1 The test for anti-static properties and the washes were carried out as in Example 1. The treated fabric showed good anti-static properties for 10 washes.
  • EXAMPLE 7 Application of disodiurn salt of 4,4-bis[2-amin0-4-(psulfoanilino)-s-triazin 6 ylamino]-stilbene-2,2-disulfonic acid and diglycidyl ether on nylon as an optical brightener A. 0.1% of 4,4-bis[2-amino-4-(p-sulfoanilino)-s-t1iazin-6-ylaminol]-stilbene-2,2'-disulfonic acid as the di sodium salt and 5% of diglycidyl ether on the Weight of the fabric were applied to nylon fabric from a single aqueous bath. The fabric was dried and cured for 3 minutes at 300 F.
  • EXAMPLE 8 Application of homofuchsine and diglycidyl ether of ethylene glycol 0n polyester fiber Aqueous solution A contained 0.5% of Cl. Basic Violet 14 (Cl. 42,510), i.e., homofuchsine, and 5% of diglycidyl ether of ethylene glycol.
  • Solution B contained 0.5% of (3.1. Basic Violet 14 alone.
  • Fabrics formed of polyester fibers were immersed in each of the above solutions at room temperature for three minutes. The excess solution was removed from each of the fabrics by squeezing to give a 70% wetpickup. After the fabrics were dried at 194 F. for 15 minutes, they were heated at 290 F. for three minutes.
  • the fabric treated with solution A contained notably more color than that treated with solution B.
  • the fabrics treated with solution A were more strongly dyed with a violet color than those treated with solution B, and the difference was greater when the fabrics were dried at 290 F.
  • a textile material may be finished with an aminoplast textile finishing resin, as for example, the formaldehyde condensates of urea, thiourea, ethylene urea, ethylene thiourea, 1,2 propylene urea, 1,3 propylene urea, guanamines, melamine, thiobisamides such as thiobispropionamide and the alkylated derivatives of these methylol compounds and then subsequently modified in accordance with the present invention.
  • an aminoplast textile finishing resin as for example, the formaldehyde condensates of urea, thiourea, ethylene urea, ethylene thiourea, 1,2 propylene urea, 1,3 propylene urea, guanamines, melamine, thiobisamides such as thiobispropionamide and the alkylated derivatives of these methylol compounds and then subsequently modified in accordance with the present invention.
  • a process for reducing the tendency of an article containing hydrophobic synthetic resins to accumulate surface charges of static electricity which comprises applying thereto at least two polyfunctional compounds capable of reacting with each other, one of said polyfunctional compounds being a member of the group consisting of 4,4- diamino-2,2-stilbenedisulfonic acid, 4,4'-diaminodibenzyl- 2,2-disulfonic acid, 4,4-diaminobiphenyl-2,2'-disulfonic acid, S-amino-l-naphthol 5 sulfonic acid, 4,4-bis(2- amino-4-(p-sulfanilino)-s-triazin 6 ylamino) stilbene- 2,2-disulfonic acid and homofuchsine and the other of said polyfunctional compounds being a diglycidyl ether of a polyhydric alcohol having an epoxy equivalency greater than 1, and thereafter combining said compounds on the article by heating the article containing them at reaction temperatures.
  • a process for reducing the tendency of an article containing hydrophobic synthetic resins to accumulate surface charges of static electricity which comprises applying thereto 4,4-diamino-2,2'-stilbenedisulfonic acid and a diglycidyl ether of a polyhydric alcohol having an epoxy equivalency greater than 1 and thereafter subjecting the so treated article to reaction temperatures.
  • a process for reducing the tendency of an article containing hydrophobic synthetic resins to accumulate surface charges of static electricity which comprises applying thereto 4,4'-diaminodibenzyl-2,2-disulfonic acid, and a diglycidyl ether of a polyhydric alcohol having an epoxy equivalency greater than 1 and thereafter subjecting the so treated article to reaction temperatures.
  • a process for reducing the tendency of an article containing hydrophobic synthetic resins to accumulate surface charges of static electricity which comprises applying thereto 4,4'-diaminobiphenyl-2,2-'disulfonic acid and a diglycidyl ether of a polyhydric alcohol having an epoxy equivalency greater than 1 and thereafter subjecting the so treated article to reaction temperatures.
  • a process for reducing the tendency of an article containing hydrophobic synthetic resins to accumulate surface charges of static electricity which comprises applying thereto 8-amino-l-naphthol-S-sulfonic acid and a diglycidyl ether of a polyhydric alcohol having an epoxy equivalency greater than 1 and thereafter subjecting the treated article to reaction temperatures.
  • a process for reducing the tendency of an article containing hydrophobic synthetic resins to accumulate surface charges of static electricity which comprises applying thereto 4,4'-diamino-2,2'-stilbenedisulfonic acid and the diglycidyl ether of ethylene glycol and thereafter subjecting the treated article to reaction temperatures.
  • a process for reducing the tendency of an article containing hydrophobic synthetic resins to accumulate surface charges of static electricity which comprises applying thereto 4,4'-diamino-2,2'-stilbenedisulfonic acid and the diglycidyl ether of ethylene glycol and thereafter subjecting the treated article to a temperature of from about F. to about 400 F.
  • a process for reducing the tendency of an article containing hydrophobic synthetic resins to accumulate surface charges of static electricity which comprises applying thereto 4,4-diam-ino 2,2. stil-benedisulfonic acid and diglycidyl ether and thereafter subjecting the treated article to reaction temperatures.
  • a process for treating textile material containing hydrophobic synthetic fibers, which textile material is subject to the accumulation of static electricity which comprises applying thereto at least two polyfunctional compounds capable of reacting with each other, one of said polyfunctional compounds being a member of the group consist-ing of 4,4-diamino-2,-2'-stilbenedisulfonic acid, 4,4 diamino-dibenzyl 2,2 :di-sul-fonic acid, 4,4- diamino-biphenyl-Z,2'-disulfonic acid, S-amino-l-naphthol 5 sulfonic acid, 4,4-bis(2-amino-4-(p-sulfanilino)- s triaZin-6-ylamino)-stilbene-2,2 disulfonic acid and homofuchsine and the other of said polyfunctional compounds being a diglycidyl ether of a polyhydric alcohol having an epoxy equivalency greater than 1, and thereafter combining said compounds on
  • a process for reducing the tendency of nylon fabric to accumulate surface charges of static electricity and to optically brighten said fabric which comprises applying thereto 4,4'-diamino-2,2'-stilbenedisulfonic acid and the diglycidyl ether of ethylene glycol and thereafter subjecting the treated fabric to reaction temperatures.
  • Synthetic hydrophobic textile material having thereon in an amount sulficient to reduce the accumulation of surface charges of static electricity a polymeric reaction product of 4,4-diamino-2,2'-stilbenedisulfonic acid and a diglycidyl ether of a polyhydric alcohol having an epoxy equivalency greater than 1.
  • Synthetic hydrophobic textile material having thereon in an amount sufficient to reduce the accumulation of surface charges of static electricity a polymeric reaction product of 4,4-diaminodibenzyl-2, 2-disulfonic acid and a diglycidyl ether of a polyhydric alcohol having an epoxy equivalency greater than 1.
  • Synthetic hydrophobic textile material having thereon in an amount suflicient to reduce the accumulat-ion of surface charges of static electricity a polymeric reaction product of 4,4-diaminobiphenyl-2,2-disulfonic acid and a :diglycidyl ether of a polyhydric alcohol having an epoxy equivalency greater than 1.
  • Synthetic hydrophobic textile material having thereon in an amount suificient to reduce the accumula tion of surface charges of static electricity a polymeric reaction product of 8-amino-l-naphthol-S-sulfonic acid and a diglycidyl ether of a polyhydric alcohol having an epoxy equivalency greater than 1.
  • Synthetic hydrophobic textile material having thereon in an amount sufficient to reduce the accumulation of surface charges of static electricity a polymeric reaction product of 4,4-diamino-2,2-stilbenedisulfonic acid and the diglycidyl ether of ethylene glycol.
  • Synthetic hydrophoblic textile material having thereon in an amount sufficient to reduce the accumulation of surface charges of static electricity a polymeric reaction product of 4,4'-diamino-2,2-stilbenedisulfonic acid and diglycidyl ether.
  • Nylon material having thereon a polymeric reaction product of 4,4'-diamino-2,2-stilbenedisulfonic acid and the diglycidyl ether of ethylene glycol.

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  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
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FR853726A FR1281706A (fr) 1960-03-01 1961-02-24 Agent polymère de traitement des textiles et procédé pour sa préparation

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Cited By (9)

* Cited by examiner, † Cited by third party
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US3337288A (en) * 1963-05-06 1967-08-22 Dainichiseika Color Chem Reactive coloring matter, processes for producing the same and processes for coloring articles with the same
US3391019A (en) * 1964-02-21 1968-07-02 Ici Ltd Process for coating shaped hydrophobic polymeric materials with reaction product of halogenotriazine and polymer containing hydroxyl, amino or mercapto group
US3563375A (en) * 1967-08-08 1971-02-16 Auby Prod Chim Method of selectively separating solid particles by electrostatic sorting in fluidized bed
US3705877A (en) * 1967-08-30 1972-12-12 Asahi Chemical Ind Antistatic synthetic resin compositions containing trazine derivatives
US3743477A (en) * 1967-07-03 1973-07-03 Sandoz Ltd Process for reserving textiles of natural polyamide fibres and of synthetic fibres dyeable with acid dyes
US3852029A (en) * 1970-10-22 1974-12-03 Ciba Geigy Ag Stable concentrated solutions of direct dyes and process for their manufacture
US3952128A (en) * 1971-09-01 1976-04-20 Kao Soap Co., Ltd. Durable antistatic agent, hydrophobic fibers and fibrous structures having durable antistatic property and method of making same
US4418164A (en) * 1982-07-19 1983-11-29 E. I. Du Pont De Nemours And Company Aramid fiber coated with polyfunctional aziridine
US5057371A (en) * 1985-06-14 1991-10-15 Minnesota Mining And Manufacturing Company Aziridine-treated articles

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US2506486A (en) * 1948-04-21 1950-05-02 Union Carbide & Carbon Corp Thermosetting resin from a diphenol and a diglycidyl ether of a diphenol
US2730427A (en) * 1952-08-13 1956-01-10 American Cyanamid Co Shrinkage control of cellulosic and wool textiles with diglycidyl ether compounds
US2752269A (en) * 1951-12-01 1956-06-26 Shell Dev Treatment of textile materials
US2839431A (en) * 1955-08-26 1958-06-17 Du Pont Antistatic agents for hydrophobic fiber
US2846397A (en) * 1949-10-14 1958-08-05 Ciba Ltd Water-soluble salts of derivatives of 4:4'-diaminostilbene-2:2'-disulfonic acid for enhancing the brightness of organic fibrous material
US2885388A (en) * 1952-08-29 1959-05-05 Ciba Ltd Polymerizable amide-like condensation products and process for their manufacture
US2892674A (en) * 1955-05-27 1959-06-30 Ici Ltd Treatment of cellulosic materials
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US2933473A (en) * 1956-07-09 1960-04-19 Gen Electric Mercaptans as catalysts for polymerization of ethoxyline resins
US2980676A (en) * 1957-07-24 1961-04-18 Ciba Ltd Glycidyl ethers of n-methylolamino-1:3:5-triazines
US3018287A (en) * 1958-11-05 1962-01-23 Fidelity Union Trust Company Optical brighteners for use with paper
US3026216A (en) * 1959-10-05 1962-03-20 Union Carbide Corp Treatment of textile fabrics with methylglycidyl ethers
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US3066005A (en) * 1958-02-01 1962-11-27 Bayer Ag Process for the treatment of hydroxyl group-containing textile materials
US3073662A (en) * 1963-01-15 Process for the production of fast dye-

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US3073662A (en) * 1963-01-15 Process for the production of fast dye-
US3046075A (en) * 1962-07-24 Dyeing and finishing textile materials
GB453431A (en) * 1935-03-06 1936-09-07 Ig Farbenindustrie Ag Improvements in the manufacture and production of condensation products
US2506486A (en) * 1948-04-21 1950-05-02 Union Carbide & Carbon Corp Thermosetting resin from a diphenol and a diglycidyl ether of a diphenol
US2846397A (en) * 1949-10-14 1958-08-05 Ciba Ltd Water-soluble salts of derivatives of 4:4'-diaminostilbene-2:2'-disulfonic acid for enhancing the brightness of organic fibrous material
US2752269A (en) * 1951-12-01 1956-06-26 Shell Dev Treatment of textile materials
US2730427A (en) * 1952-08-13 1956-01-10 American Cyanamid Co Shrinkage control of cellulosic and wool textiles with diglycidyl ether compounds
US2885388A (en) * 1952-08-29 1959-05-05 Ciba Ltd Polymerizable amide-like condensation products and process for their manufacture
US2903381A (en) * 1954-09-03 1959-09-08 Shell Dev Treatment of synthetic textiles with a polyepoxide having a plurality of 1,2 epoxy groups
US2892674A (en) * 1955-05-27 1959-06-30 Ici Ltd Treatment of cellulosic materials
US3030247A (en) * 1955-07-28 1962-04-17 Minnesota Mining & Mfg Stable heat-curing epoxy resin compositions
US2839431A (en) * 1955-08-26 1958-06-17 Du Pont Antistatic agents for hydrophobic fiber
US2933473A (en) * 1956-07-09 1960-04-19 Gen Electric Mercaptans as catalysts for polymerization of ethoxyline resins
US2980676A (en) * 1957-07-24 1961-04-18 Ciba Ltd Glycidyl ethers of n-methylolamino-1:3:5-triazines
US3066005A (en) * 1958-02-01 1962-11-27 Bayer Ag Process for the treatment of hydroxyl group-containing textile materials
US3018287A (en) * 1958-11-05 1962-01-23 Fidelity Union Trust Company Optical brighteners for use with paper
US3026216A (en) * 1959-10-05 1962-03-20 Union Carbide Corp Treatment of textile fabrics with methylglycidyl ethers

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3337288A (en) * 1963-05-06 1967-08-22 Dainichiseika Color Chem Reactive coloring matter, processes for producing the same and processes for coloring articles with the same
US3391019A (en) * 1964-02-21 1968-07-02 Ici Ltd Process for coating shaped hydrophobic polymeric materials with reaction product of halogenotriazine and polymer containing hydroxyl, amino or mercapto group
US3743477A (en) * 1967-07-03 1973-07-03 Sandoz Ltd Process for reserving textiles of natural polyamide fibres and of synthetic fibres dyeable with acid dyes
US3563375A (en) * 1967-08-08 1971-02-16 Auby Prod Chim Method of selectively separating solid particles by electrostatic sorting in fluidized bed
US3705877A (en) * 1967-08-30 1972-12-12 Asahi Chemical Ind Antistatic synthetic resin compositions containing trazine derivatives
US3852029A (en) * 1970-10-22 1974-12-03 Ciba Geigy Ag Stable concentrated solutions of direct dyes and process for their manufacture
US3952128A (en) * 1971-09-01 1976-04-20 Kao Soap Co., Ltd. Durable antistatic agent, hydrophobic fibers and fibrous structures having durable antistatic property and method of making same
US4418164A (en) * 1982-07-19 1983-11-29 E. I. Du Pont De Nemours And Company Aramid fiber coated with polyfunctional aziridine
US5057371A (en) * 1985-06-14 1991-10-15 Minnesota Mining And Manufacturing Company Aziridine-treated articles

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BE600676A (xx) 1900-01-01

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