US3687605A - Stabilization of wool through treatment with a reducing agent and a polymer or polymer forming materials - Google Patents

Stabilization of wool through treatment with a reducing agent and a polymer or polymer forming materials Download PDF

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US3687605A
US3687605A US533844A US3687605DA US3687605A US 3687605 A US3687605 A US 3687605A US 533844 A US533844 A US 533844A US 3687605D A US3687605D A US 3687605DA US 3687605 A US3687605 A US 3687605A
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fabric
glycol
diisocyanate
polymer
reducing agent
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Larry B Farmer
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Deering Milliken Research Corp
Milliken Research Corp
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    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/564—Polyureas, polyurethanes or other polymers having ureide or urethane links; Precondensation products forming them
    • D06M15/568—Reaction products of isocyanates with polyethers
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/564—Polyureas, polyurethanes or other polymers having ureide or urethane links; Precondensation products forming them
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
    • D06M2200/20—Treatment influencing the crease behaviour, the wrinkle resistance, the crease recovery or the ironing ease
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
    • D06M2200/45—Shrinking resistance, anti-felting properties
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
    • D06M2200/50—Modified hand or grip properties; Softening compositions
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/04—Polyester fibers
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/09—Polyolefin
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/11—Isocyanate and carbonate modification of fibers
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/21—Nylon
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/916—Natural fiber dyeing
    • Y10S8/917—Wool or silk

Definitions

  • US. Cl. 8127.6 6 Claims ABSTRACT OF THE DISCLOSURE A two step durable' setting in the desired configuration of textile materials containing keratinous fibers comprising (1) an external stabilization and (2) an internal stabilization.
  • the external stabilization involves polymer formation through treatment with a polyisocyanate and an active hydrogen containing polymer.
  • the internal stabilization involves treatment with a reducing agent.
  • This invention relates to a textile fabric which contains keratinous fibers and which has a propensity to conform durably to a preselected configuration, and more specifically, to wool fabrics having creases which are durable to laundering and dry cleaning operations.
  • Garments made from wool fabrics have been sprayed with reducing agent solutions and pressed on a steam press in an attempt to produce durable creases in the garments.
  • the creases as produced are quite durable to mere wetting but will not withstand a combination of wetting and agitation, such as occurs in a washing machine.
  • the preferred process for splitting internal linkages of keratinous fibers is treatment with a reducing agent.
  • Preferred among the linkage reforming processes are steam and heat processes.
  • the preselected configurations which are contemplated include any shape desired in the fabrics or garments made from such fabrics, e.g., pleats, creases, texturing effects, such as pebble textures, and the like.
  • the external setting of the keratinous fiber is accomplished by means of a polymeric chemical reagent.
  • Typical examples of such setting processes are additive type shrinkproofing processes wherein polymeric reagents are added to keratinous fabrics. These reagents preferably react with the keratinous component for improved washability characteristics.
  • the external stabilization of the keratinous fiber may also be accomplished by means of coating the fibers with a non-reactive polymeric coating composition so as to secure the fibers in the desired configuration by means of the mechanical forces exerted by the coating, e.g., according to the Wurlan process developed at the Western Regional Laboratories of the United States Department of 3,687,605 Patented Aug. 29, 1972 Agriculture.
  • the preferred external setting medium is a medium of the type which produces new chemical bonds by reacting with a keratin fiber
  • the only prerequisite for this type of reagent is that at least some of the new chemical bonds be formed on the surface of the keratinous fiber, that is to say chemical bonds may be formed internally and externally, but at least some bonds must be formed on the surface of the fiber.
  • interfacial polymerization systems such as those involving the formation of poly(hexamethylene sebacate) through interfacial polymerization techniques, treatments with reactive terpolymers based on vinyl type monomers, treatments with polyepoxide-polyamine compositions, treatments with reactive polyurethanes and treatments with emulsions of certain acrylic esters such as, for instance, polymethylmethacrylate, polyethylmethacrylate, polypropylmethacrylate and polybutylmethacrylate.
  • interfacial polymerization systems such as those involving the formation of poly(hexamethylene sebacate) through interfacial polymerization techniques, treatments with reactive terpolymers based on vinyl type monomers, treatments with polyepoxide-polyamine compositions, treatments with reactive polyurethanes and treatments with emulsions of certain acrylic esters such as, for instance, polymethylmethacrylate, polyethylmethacrylate, polypropylmethacrylate and polybutylme
  • polymeric external stabilizing agents provides many advantages over techniques involving the use of monomeric oxidizing agents such as sodium chlorite and various permanganate salts.
  • Polymeric compounds not only provide a higher level of stability to washing in fabrics so treated, but also provide a higher level of finish stability as well as flat drying properties than is possible with monomeric type treating agents.
  • a wool fabric is first treated with a monomeric shrinkproofing agent and then durably set with reducing agent solutions, the results, if anything, are less than additive.
  • the fabric, during washing, tends to shrink slightly more than if no reducing agent treatment had been employed and the flat drying properties and finish are not satisfactory.
  • the most preferred external stabilizing agents for purposes of the invention are isocyanate reaction products. These reaction products, in combination with the internal stabilizing treatment, provide greatly improved washability characteristics. For example, garments made from fabrics treated with these products accept creases quite readily and retain these creases after washing and tumble drying to a much greater extent when compared with other externally stabilized fabrics, although these latter products are entirely satisfactory.
  • isocyanate reaction products selected from two general catagories, the first of which is a urethane prepared from a polyfunctional isocyanate and a polymeric polyhydroxy compound and the second of which is the reaction product of a polyfunctional isocyanate and polymeric polyfunctional compound selected from the group consisting of polyesters, polyamides, poly-epoxides and reaction products of phenol and alkanol oxides, formaldehyde resins, hydrogenation products of olefincarbon monoxide copolymers and polyepihalohydrins.
  • the isocyanate reaction products may be applied to the fabric as a single solution in pre-polymer form or in one-shot applications forming the isocyanate reaction product on the fabric in situ.
  • the ratio of isocyanate to active hydrogen compound be at least about 0.4, but most preferably, greater than 1.0, e.g., from 1.01 to about 2.0, preferably 1.05 to 1.6.
  • Systems containing an excess of isocyanate are much more highly reactive with keratin fibers, so that stabilization is provided to the desired level, permitting washing with little or no degradation of the hand, or feel, of the fabric.
  • configurations imparted to such fabrics by subsequent reducing agent treatments are durable to washing even at low levels of polymer, e.g., as little as 1%, but preferably between 3 and 10%, although amounts on the order of 15-25% produce excellent results, even though producing stiffening effect on fabric" so treated.
  • pre-polymer herein is meant the reaction product of the polyfunctional isocyanate and the preselected second polymeric compound carried to an extent below which a gel is produced which is insoluble in one of the organic solvents for each of the two reaction components and particularly the chlorinated hydrocarbons.
  • the prepolymer is prepared from an excess of isocyanate as preferred, the resulting product is believed to be an isocyanate-terminated polyurethane, which is highly reactive with keratin fibers.
  • one-shot as employed herein is meant to define a process wherein the isocyanate and active hydrogen compound are applied to the substrate material directly from solution.
  • the desired polymer is then formed in situ on the fabric.
  • the degree of polymerization of the resulting polymer exceeds that of the prepolymer.
  • aryl diisocyanates such as 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, 4,4'-diphenylmethane diisocyanate, p-phenylene diisocyanate, 1,5-naphthylene diisocyanate, m-phenylene diisocyanate, diphenyl-4,4'-diis0cyanate, azbenzene-4,4- diisocyanate, diphenylsulphone-4,4-diisocyanate, l-isopropylbenzene-Ia', S-diisocyanate, 1-methyl-phenylene-2,4-diisocyanate, naphthylene-1,4-diisocyanate, diphenyl-4,4'-diisothiocyanate and diisocyanate, benzene-l, 2,4-triiso
  • Additional isocyanates include polymethylene diisocyanates and diisothiocyanates, such as ethylene diisocyanate, dimethylene diisocyanate, dodecamethylene diisocyanate, hexamethylene diisocyanate, tetramethylene diisocyanate, pentamethylene diisocyanate, and the corresponding diisothiocyanates; alkylene diisocyanates and diisothiocyanates such as propylene-1,2-diisocyanate, 2,3-dimethyltetramethylene diisocyanate and diisothiocyanate, butylene-1,2- diisocyan'ate, butylene-1,3-diisothiocyanate, and butylene- 1,3-diisocyanate; alkylidene diisocyanates and diisothiocyanates such as ethylidene diisocyanate (CHgCH (N00) and heptylidene diisothiocyanate cyclo
  • the preferred diisocyanates, diisothiocyanates and mixed isocyanate-isothiocyanates have the general formula ZCNRNCZ in which R is a divalent hydrocarbon radical, preferably aryl, and Z is a chalcogen of atomic weight less than 33.
  • R is a divalent hydrocarbon radical, preferably aryl
  • Z is a chalcogen of atomic weight less than 33.
  • tolylene 2,4- diisocyanate is prefererd.
  • polymeric polyhydroxy compound is meant a linear long-chain polymer having terminal hydroxyl groups including branched, polyfunctional polymeric hydroxy compounds as set forth below.
  • suitable polymeric polyhydroxy compounds there are included polyether polyols such as polyalkyleneether glycols, and polyalkylene-aryleneether-thioether glycols and polyalkyleneether triols. Polyalkyleneether glycols and triols are preferred. Mixtures of these polyols may be used when desired.
  • the polyalkyleneether glycols may be represented by the formula HO(RO),,H, wherein R is an alkylene radical which need not necessarily be the same in each instance and n is an integer.
  • Representative glycols include polyethyleneether glycol, polypropyleneether glycol, polytrimethyleneether glycol, polytetramethylene ether glycol, polypentamethyleneether glycol, polydecarnethyleneether glycol, polytetramethylene formal glycol and poly-1,2-dimethylethyleneether glycol. Mixtures of two or more polyalkyleneether glycols may be employed if desired.
  • Representative polyalkyleneether triols are made by reacting one or more alkylene oxides with one or more low molecular weight aliphatic triols.
  • the alkylene oxides most commonly used have molecular weights between about 44 and 250. Examples include: ethylene oxide; propylene oxide; butylene oxide; 1,2-ep0xybutane; 1,2-epoxyhexane; 1,2-epoxyoctane; 1,2-epoxyhexadecane; 2,3-epoxybutane; 3,4-epoxyhexane; 1,2-epoxy-S-hexene; and 1,2-epoxy-3-butane, and the like. Ethylene, propylene, and butylene oxides are preferred.
  • alkylene oxides having cyclic substituents may be present, such as styrene oxide, cyclohexene oxide, 1,2-epoxy-2-cyclohexylpropane, and a methyl styrene oxide.
  • the aliphatic triols most commonly used have molecular weights between about 92 and 250. Examples include glycerol, 1,2,6-hexanetriol; l,l,1-trimethylolpropane; 1,1,l-trimethylolethane; 2,4-dimethylol-2- methylol-pentanediol-'1,5 and the trimethylether of sorbitol.
  • polyalkyleneether triols include: polypropyleneether triol (M.W. 700) made by reacting 608 parts of 1,2-propyleneoxide with 92 parts of glycerine; polypropyleneether triol (M.W. 1535) made by reacting 1401 parts of 1,2-propyleneoxide with 134 parts of trimethylolpropane; polypropyleneether triol (M.W. 2500) made by reacting 2366 parts of 1,2-propyleneoxide with 134 parts of 1,2,6-hexanetriol; and polypropyleneether triol (M.W. 6000) made by reacting 5866 parts of 1,2-pr0pyleneoxide with 134 parts of 1,2,6-hexanetriol.
  • M.W. 700 polypropyleneether triol
  • M.W. 1535 made by reacting 1401 parts of 1,2-propyleneoxide with 134 parts of trimethylolpropane
  • Additional suitable polytriols include polyoxypropylene triols, polyoxybutylene triols, Union Carbides Niax triols LG56, L642, LG112 and the like; Jeiferson Chemicals Triol G-4000 and the like: Actol 32-160 from National Aniline and the like.
  • the polyalkylene-aryleneether glycols are similar to the polyalkyleneether glycols except that some arylene radicals are present.
  • Representative arylene radicals include phenylene, naphthalene and anthracene radicals which may be substituted with various substituents, such as alkyl groups.
  • substituents such as alkyl groups.
  • alkyleneether radicals there should be at least one alkyleneether radical having a molecular weight of about 500 for each arylene radical which is present.
  • polyalkyleneether-thioether glycols and the polyalkylene-aryleneether glycols are similar to the abovedescribed polyether glycols, except that some of the ether oxygen atoms are replaced by sulfur atoms.
  • These glycols may be conveniently prepared by condensing together various glycols, such as thiodiglycol, in the presence of a catalyst, such as p-toluene-sulfonic acid.
  • polymeric polyfunctional compound is meant a long-chain polymer of the types described containing at least two groups having at least one active hydrogen atom as determined by the Zerewitinolf method.
  • polymeric polyfunctional compound there may be utilized such compounds as polyesters, polyamides, polyepoxides, reaction products of phenols and alkylene oxides, formaldehyde resins, hydrogenation products of olefine-carbon monoxide copolymers, and polyepihalohydrins.
  • polyesters suitable for use in accordance with this invention are well known and are generally prepared by conducting a condensation reaction between an excess of a monomeric or polymeric polyhydroxy compound and a polyacid or by esterifying a hydroxy substituted acid and a polyhydroxy alcohol.
  • alkane dibasic acids alkene dibasic acids, cycloalkene dibasic acids, cycloalkane dibasic acids, aryl dibasic acids, or any of the foregoing types wherein the hydrocarbon radical is substituted with an alkyl, alkenyl, cycloalkyl, cycloalkenyl or aryl radical.
  • dibasic carboxylic acids which can be employed for reaction with polyols in preparation of polyesters for use in accordance with this invention include the following: succinic; monomethyl succinic; glutaric; adipic; pimelic; suberic; azelaic; sebacic; brassylic; thapsic; 6- oxoundecanedioic; octadecanedioic acid; S-octadecenedioic acid; ricinoleic acid; 6,8-octadecadienedioic acid; malic; and the like.
  • acids include: unsaturated acids such as maleic, fumaric, glutaconic, and itaconic; the cycloalkane dicarboxylic acids such as cyclopentane-1,2- dicarboxylic and cyclopentane-1,3-dicarboxylic; aromatic dicarboxylic acids such as phthalic, isophthalic, terephthalic, naphthalene 1,2 dicaroxylic, naphthalene 1,3 dicarboxylic, naphthalene-1,4-dicarboxylic, naphthalene-1,5- dicarboxylic, naphthalene-1,8-dicarboxylic, diphenyl-2,2'- dicarboxylic, diphenyl-4,4'-dicarboxylic and diphenyl-2,4'- dicarboxylic; and aliphatic-aromatic dicarboxylic acids such as 2,6 dimethylbenzene-1,4-dicarboxylic acid, and
  • Representative monomeric polyols for reaction with the above acids for the production of polyesters for use in accordance with this invention include the polyalkyleneether glycols represented by the formula HO(RO) H, wherein R is an alkylene radical which need not necessarily be the same in each instance and n is an integer.
  • Representative glycols include polyethyleneether glycol, polypropyleneether glycol, polytrirnethyleneether glycol, polytetramethyleneether glycol, polypentamethyleneether glycol, polydecamethyleneether glycol, polytetramethyleneformal glycol and poly-l,Z-dimethylethyleneeether glycol. Mixtures of two or more polyalkyleneether glycols may be employed if desired.
  • Representative polyalkyleneether triols are made by reacting one or more alkylene oxides with one or more low molecular weight aliphatic triols.
  • the alkylene oxides most commonly used have molecular weights between about 44 and 250. Examples include: ethylene oxide; propylene oxide; butylene oxide; 1,2-epoxybutane; 1,2- epoxyhexane; 1,2-epoxyctane; 1,2-epoxyhexadccane; 2,3- epoxybutane; 3,4-epoxyhexane; 1,2-epoxy--hexene; and 1,2-epoxy-3-butane, and the like. Ethylene, propylene, and butylene oxides are preferred.
  • alkylene oxides having cyclic substituents may be present, such as styrene oxide, cyclohexene oxide, 1,2-epoxy-2-cyclohexylpropane, and amethyl styrene oxide.
  • the aliphatic triols most commonly used have molecular weights between about 92 and 250. Examples include glycerol; 1,2,6-hexanetriol; 1,1,1-trimethylolpropane; 1,1,1-trimethylolethane; 2,4-dimethylol 2-methylol-pentanediol-1,5 and the trimethylether of sorbitol.
  • polyalkyleneether triols include: polypropyleneether triol (M.W. 700) made by reacting 608 parts of 1,2-propyleneoxide with 92 parts of glycerine; polypropyleneether triol (M.W. 1535) made by reacting 1401 parts of 1,2-propyleneoxide with 134 parts of trimethylolpropane; polypropyleneether triol (M.W. 2500) made by reacting 2366 parts of 1,2-propyleneoxide with 134 parts of 1,2,6-hexanetriol; and polypropyleneether triol (M.W. 6000) made by reacting 5866 parts of 1,2 propyleneoxide with 134 parts of 1,2,6- hexanetriol.
  • M.W. 700 polypropyleneether triol
  • M.W. 1535 made by reacting 1401 parts of 1,2-propyleneoxide with 134 parts of trimethylolpropane
  • polypropyleneether triol (M.W. 2500) made by react
  • Additional suitable polytriols include polyoxypropylene triols, polyoxybutylene triols, Union Carbides Niax triols LG56, LG42, LGll2 and the like; Jefferson Chemicals Triol G-4000 and the like; Actol 32160 from National Aniline and the like.
  • the polyalkylene-aryleneether glycols are similar to the polyalkyleneether glycols except that some arylene radicals are present.
  • Representative arylene radicals include phenylene, naphthalene and anthracene radicals which may be substituted with various substituents, such as alkyl groups.
  • substituents such as alkyl groups.
  • alkyleneether radicals there should be at least one alkyleneether radical having a molecular weight of about 500 for each arylene radical which is present.
  • polyalkyleneether-thioether glycols and the polyalkylene-aryleneether glycols are similar to the above described polyether glycols, except that some of the etheroxygen atoms are replaced by sulfur atoms.
  • This glycols may be conveniently prepared by condensing together various glycols, such as thiodiglycol, in the presence of a catalyst, such as p-toluene-sulfonic acid.
  • Additional polyesters include those obtained by reacting one or more of the above acids with a mixture of polyhydric alcohols comprising (1) polyhydric alcohols of the general formula:
  • alkylene means a divalent saturated aliphatic radical having at least 2 carbon atoms, preferably not more than 5 carbon atoms
  • x, y and z are whole numbers and the sum of x, y and z is from 3 to 10, preferably from 3 to 6, at least two of the -(alkylene-O- ⁇ H groups contain primary alcoholic hydroxyl groups and R is a large alkyl group containing from 10 to 25 carbon atoms
  • polyhydric alcohols containing only carbon, hydrogen and oxygen, and the polyhydric alcohols from (1) and (2) are employed in such proportions that from 1 to 15 alcoholic OH groups are contributed by (l) for every 10 alcoholic OH groups contributed by (2).
  • polyepoxides used in accordance with the invention are organic compounds having at least two epoxy groups per molecule and may be saturated or unsaturated, aliphatic, cycloaliphatic, aromatic or heterocyclic and may be substituted with non-interfering substituents such as hydroxyl groups, ether radicals, and the like.
  • Polyepoxides containing ether groups generally designated as polyepoxide polyethers, may be prepared as well known in the art by reacting a polyol with a halogen-containing epoxide employing at least 2 moles of the halogen-containing epoxide per mole of polyol.
  • epichlorohydrin may be reacted with a polyhydric phenol in an alkaline medium.
  • the halogencontaining epoxide is reacted with a polyhydric alcohol in the presence of an acid-acting catalyst such as hydrofluoric acid or boron trifluoride and the product is then reacted with an alkaline compound to effect a dehydrohalogenation.
  • an acid-acting catalyst such as hydrofluoric acid or boron trifluoride
  • a preferred example of the halogen-containing epoxide is epichlorohydrin; others are epibromohydrin, epiodohydrin, 3-chloro-1,2-epoxybutane, 3-bromo- 1,2-epoxyhexane, and 3-chloro-1,2-epoxy-octane.
  • Illustrative examples of polyepoxide polyethers are as follows:
  • polyepoxide polyethers may or may not contain hydroxy groups, depending primarily on the proportions of halogen-containing epoxide and polyol employed.
  • Polyepoxide polyethers containing polyhydroxyl groups may also be prepared by reacting, in known manner, a polyhydric alcohol or polyhydric phenol with a polyepoxide in an alkaline medium.
  • Illustrative examples are the reaction product of glycerol and diglycidyl ether, the reaction product of sorbitol and his(2,3-epoxy-2-methylpropyl)ether, the reaction product of pentaerythritol and 1,2,3,5-diepoxy pentane, the reaction product of 2,2-bis(parahydrxyphenyl)propane and bis(2,3 epoxy 2 methylpropyl) ether, the reaction product of resorcinol and diglycidyl ether, the reaction product of catechol and diglycidyl ether, and the reaction product of 1,4-dihydroxy-cyclohexane and diglycidyl ether.
  • Polyepoxides which do not contain ether groups may be employed as for example 1,2,5,6-diepoxyhexane; butadiene dioxide (that is, 1,2,3,4-diepoxybutane); isoprene dioxide; limonene dioxide.
  • polyepoxides which contain ether groups that is, polyepoxide polyethers. More particularly I prefer to use the polyepoxide polyethers of the class of glycidyl polyethers of polyhydric alcohols of glycidyl polyethers of polyhydric phenols. These compounds may be considered as being derived from a polyhydric alcohol or polyhydric phenol by etherification with at least two glycidyl groups The alcohol or phenol moiety may be completely etherified or may contain residual hydroxy groups.
  • Typical examples of compounds in this category are the glycidyl polyethers of glycerol, glycol, diethylene glycol, 2,2-bis (parahydroxyphenyl) propane, or any of the other polyols listed hereinabove as useful for reaction with halogencontaining epoxides.
  • Many of the specific glycidyl polyethers derived from such polyols are set forth hereinabove.
  • Particularly preferred among the glycidyl polyethers are those derived from 2,2-bis(parahydroxyphenyl) propane and those derived from glycerol.
  • the compounds derived from the first-named of these polyols have the structure pounds are not technically resins in the state in which they are sold and employed because they are of relatively low molecular weight and thus do not have resinous properties as such. It is only when the compounds are cured that true resins are formed.
  • manufacturers catalogs conventionally list as epoxy resins such relatively low-molecular weight products as the diglycidyl ether of 2,2-bis(parahydroxyphenyl)propane, the diglycidyl ether of glycerol, and similar polyepoxide polyethers having molecular Weights substantially less than 1,000.
  • mixtures of different polyepoxides it has been found that especially desirable results are attained by employing mixtures of two commercially available polyepoxides, one being essentially a diglycidyl ether of glycerol, the other being essentially a diglycidyl ether of 2,2 bis(parahydroxyphenyl)propane. Particularly preferred to attain such result are mixtures containing more than t and less than 10 parts by weight of the glycerol diglycidyl ether per part by weight of the diglycidyl ether of 2,2-bis (parahydroxyphenyl propane.
  • the polyamides used in accordance with the invention are those derived from polyamines and polybasic acids. Methods of preparing these polyamides by condensation of polyamines and polycarboxylic acids are well known in the art. One may prepare polyamides containing free amino groups or free carboxylic acid groups or both free amino and free carboxylic acid groups.
  • the polyamides may be derived from such polyamines as ethylene diamine, diethylene triamine, triethylene tetramine, tetraethylene pentamine, 1,4-diaminobutane, 1,3-diaminobutane, hexamethylene diamine, 3-(N-isopropylamino)propylamine, 3,3'-imino-bispropylamine, and the like.
  • Typical polycarboxylic acids which may be condensed with the polyamines to form polyamides are glutaric acid, adipic acid, pimelic acid, suberic acid,fugic acid, sebacic acid, isophthalic acid, terephthalic acid, betamethyl adipic acid, 1,2-cyclohexane dicarboxylic acid, malonic acid, polymerized fatty acids, and the like.
  • the polyamides may have molecular weights varying about from 1,000 to 10,000 and melting points about from 20-200" C.
  • Particularly preferred for the purpose of this invention are the polyamides derived from aliphatic polyamines and polymeric fatty acids.
  • Such products are disclosed for example by Cowan et al., Pat. No. 2,450,940.
  • Typical of these polyamides are those made by condensing ethylene diamine or diethylene triamine with polymeric fatty acids produced from the polymerization of drying or semi-drying oils, or the free acids, or simple aliphatic alcohol esters of such acids.
  • the polymeric fatty acids may typically be derived from such oils as soybean, linseed, tung, perilla, oiticia, cottonseed, corn, tall, sunflower, safilower, and the like.
  • the unsaturated fatty acids combine to produce a mixture of dibasic and higher polymeric acids.
  • the mixture contains a preponderant proportion of dimeric acids with lesser amounts of trimeric and higher polymeric acids, and some residual monomeric acid.
  • Particularly preferred are the polyamides of low melting point (about wherein it varies between zero and about 10, corresponding' to a molecular weight about from 350 to 8,000.
  • n has a low value, i.e., less than 5, most preferably where n is zero.
  • the polyepoxide polyethers are conventionally termed as epoxy resins even though the com- 20-90 C.) which may be produced by heating together an aliphatic polyamine, such as diethyleuetriamine, triethylene tetramine, 1,4-diaminobutane, 1,3-diaminobutame, and the like with the polymerized fatty acids.
  • an aliphatic polyamine such as diethyleuetriamine, triethylene tetramine, 1,4-diaminobutane, 1,3-diaminobutame, and the like
  • Typical among these is a polyamide derived from diethylene triamine and dimerized soybean fatty acids.
  • the polyamides derived from aliphatic polyamides and polymerized fatty acids, like the polyepoxides, are often referred to in the trade as resins even though not actually resins in the state in which they are sold and applied. Particularly good results are obtained in the use of low
  • condensation product of a phenol and an alkylene oxide may be used such as, for example, the condensation product of cresol or 4,4'-isopropylidenediphenol with one of the aforementioned alkylene oxides.
  • Any suitable hydrogenation product of olefin-carbon monoxide copolymers may be used such as, for example, the hydrogenation product of an ethylene-propylene-carbon monoxide copolymer and others disclosed in US. Patent 2,839,478, issued to Wilms et als., June 17, 1958, and US. Patent 2,495,292, issued to Scott, J an. 24, 1950.
  • the polyfunctional isocyanate and polymeric polyfunctional compound or polyfunctional isocyanate and polymeric polyhydroxy compound as the case may be with or without a coreactant and unblocked or blocked in a one-shot procedure with the keratinous fibers in the presence of a catalyst.
  • a catalyst Any of the well-known catalysts for the reaction of active hydrogen atoms with isocyanates may be used. Of these catalysts which are used in the production of polyurethanes, organo-tin or organozinc compounds are preferred. Particularly preferred are either stannous octoate or zinc naphthenate.
  • the various isocyanate reaction product systems described above preferably are applied to the keratinous fiber containing fabric in the form of a solution, the solution employing a non-reactive solvent although aqueous emulsions may be utilized if desired.
  • non-reactive as used herein is meant a solvent in which reactivity between the isocyanate and active-hydrogen containing components of the solvent mixture even in the presence of catalyst is substantially inhibited.
  • Small amounts of reactive solvents may be present provided the amount present is sufficiently low as not to precipitate a substantial amount of the components with which it is reacted. In other words, sufiicient components remain reactive with the keratin fibers to provide adequate inhibition of shrinkage and/or settability in the fabric or other structure being treated.
  • Suitable organic solvents include halogenated hydrocarbons such as trichloroethylene, methylene chloride, perchloroethylene, ethylene dichloride, chloroform and the like, aromatic solvents such as toluene, xylene, benzene, mixed aromatics, such as the Solvesso types and the like, n-butyl acetate, n-butyl ether, n-butyl phosphate, p-dioxane, ethyl oxalate, methyl isobutyl ketone, pyridine, quinoline, N,N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, 2,2,4-trimethyl-pentane and the like. Mixtures of solvents may be used.
  • halogenated hydrocarbons such as trichloroethylene, methylene chloride, perchloroethylene, ethylene dichloride, chloroform and the like
  • aromatic solvents such as
  • the internal setting of the keratinous fibers is preferably accomplished by means of a reducing agent.
  • a reducing agent Such compounds are well-known in the art and have the ability to rupture polymeric linkages, within the structure of keratin. These ruptured linkages, specifically the disulfide linkages, may be at least partially reformed While holding the fiber in a desired configuration, thereby setting this configuration durably in the fiber.
  • the reaction which appears to take place in setting the keratinous fibers in the new shape is reformation of the cystine linkage and reformation of hydrogen bonds and/or hydrophobic bonds of the keratinous fibers, the bonds and linkages having previously been split by contact with the reducing agent.
  • the cystine linkages are split and reunited to form at least some of the disulfide bonds.
  • lower alkanolamine sulfites such as monoethanolamine sulfite and isopropanolamine sulfites, and others containing up to about 8 carbon atoms in the alkyl chain, such as n-propanolamine sulfite, n-butanolamiue sulfite, dimethylbutanolamine sulfite, dimethylhexanolamine sulfite and the like; metallic formaldehyde sulfoxylates, such as zinc formaldehyde sulfoxylate, the alkali metal sulfoxylates, such as sodium formaldehyde sulfoxylate and potassium formaldehyde sulfoxylate; alkali metal borohydrides, such as soduim borohydride, potassium borohydride and sodium potassium borohydrate; alkali metal sulfites, such as sodium or potassium bisulfite, sulfite,
  • Urea constitutes the most readily available and desirable auxiliary agent, although any other material which will swell kertinous fibers in an aqueous medium is suitable.
  • guanidine compounds such as hydrochloride; formamide, N,N-dimethylformamide, acetamide, N,N-dimethylacetarnide, thiourea, dimethylsulfoxide, phenol, lithium salts, such as the chloride, bromide, and iodide and the like are similarly useful.
  • low molecular weight polyhydroxy compound a compound containing more than one hydroxy group and having a molecular weight preferably no greater than about 4000.
  • the most readily available and desirable compound comprises ethylene glycol.
  • a particularly preferred group of glycols includes the polyfunctional glycols having terminal hydroxyl groups separated by 2 to 10 methylene groups, including, of course, the preferred ethylene glycol as well as trime-thylene glycol, tetramethylene glycol, pentamethylene glycol, hexamethylene glycol, and decamethylene glycol, or such glycols as 1,2-propylene glycol, dipropylene glycol, 1,3-butylene glycol, diethylene glycol, polyethylene glycol or the like.
  • Polyfunctional compounds containing more than 2 hydroxyl groups include the polyfunctional alcohol glycerols such as glycerine and diethylglycerol as well as trimethylol ethane, trimethylol butane, tris-hydroxymethyl-amino methane and others.
  • Glycol ethers such as the water-soluble or dispersible polyethylene glycols or polypropylene glycols having molecular weights preferably no greater than about 4000 also provide satisfactory results when utilized in accordance with this invention.
  • the reducing agent with or without the auxiliary agent or polyhydroxy compound may be applied to the fabric in any desired amount, depending upon the degree of reducing desired. In general, optimum results are obtained when aqueous solutions containing from about 0.01 to about 20% by weight and most preferably from 1 to about 10% by weight of the reducing agent is applied to the fabric.
  • the swelling agent or polyhydroxy compound if employed may be applied to the fabric by addition to the aqueous solution of reducing agent of amounts of from about 3 to about 30% and, most preferably, from about 5 to about 20% by weight. Higher concentrations may be utilized where the fabric is to be exposed to the treating medium for only a short time.
  • the fabric may be converted to a garment and the garment subjected to the reducing agent treatment for setting durable configurations in the garment.
  • the conversion to a garment is preferable where the object of the process is to produce creases in the garment which are durable to home laundering.
  • the externally stabilized fabric may be impregnated with the desired reducing agent solution, preferably containing a swelling agent or low molecular weight polyhydroxy compound, and then dried under conditions which are not capable of reforming any split linkage in the keratinous fibers.
  • the resulting fabric is thereby presensitized for subsequent durable setting in garment or fabric form on any of the well-known equipment used for setting operations.
  • a particular advantage of such a fabric, with or without a swelling agent and/ or low molecular weight polyhydroxy compound, can be made into garments and the garments durably set by standard pressing and curing, for example, using a Hoffman press to impart creases to the garments and then reforming any split linkages in a curing oven.
  • the configurations set in garments in this manner are durable, at the very least, to the wetting,
  • washa'bility characteristics that water in an amount of at least about preferably to 40%, or even more, be applied to the presensitized fabrics before pressing and curing.
  • the mechanical steps of producing a texture effect, crease, and the like may be carried out with any of the well-known existing pieces of textile finishing equipment.
  • a Hoffman press is preferred for the preparation of creases.
  • the process of this invention is applicable to any keratinous substrate, including, of course, fabrics made from blends of keratinous fibers with other natural fibers, including silk, cellulosic fiber and the like, or with synthetic fibers, such as synthetic cellulosic fibers including acetylated cellulose, for example, the cellulose acetates, acetylated rayon, rayon per se and the like; polyamides, particularly nylon, both 6 and 66 types; polyesters, such as polyethylene terephthalate and the like; polyolefins, such as polyethylene, polypropylene and the like; acrylic fibers such as those produced from acryonitrile and copolymers thereof, and the like.
  • synthetic fibers including acetylated cellulose, for example, the cellulose acetates, acetylated rayon, rayon per se and the like; polyamides, particularly nylon, both 6 and 66 types; polyesters, such as polyethylene terephthalate and the like; polyolef
  • keratinous fibers for example, at least about 20%, prefera'bly at least about 40%, by weight be present in the substrates being treated.
  • EXAMPLE I Into a jacketed stainless steel reactor is poured 225 lbs. of polypropylene glycol adduct of glycerin having a molecular weight of about 5,000. The reactor is then closed and the pressure therein reduced to about 10 mm. mercury after which the reactor is flushed with dry nitrogen. The pressure regulation and flushing operation is repeated for 3 cycles, after which 23 lbs. of dry toluene is poured into the reactor. A blanket of nitrogen gas is maintained in the vessel throughout the reaction. The pressure is again reduced to 10 mm. mercury and the reactor is heated to 140 C. to distill ofi the toluene, after which it is cooled to room temperature using cold water in the jacket around the reactor. The pressure is returned to room conditions.
  • a solution is then prepared from the 70% solution of the prepolymer by dilution with additional trichloroethylene, the dilution being conducted to the point so that a pickup of 3.5% based on the dry weight of the fabric of prepolymer is picked up on the fabric.
  • N,N, N'N'tetrakis Z-hydroxy propyl ethylene diamine in the amount of about 3% of the weight of pure prepolymer is added to the bath.
  • the solution is padded onto the wool fabric and the padded fabric is then placed in an oven at F. for 5 minutes for drying and then placed in the second oven at 250 F. for 5 minutes for curing.
  • the treated fabric is then scoured, dried and pressed. Trousers are then prepared from the urethane treated fabric.
  • the trousers are sprayed with a 6.4% solution of monoisopropynolamine sulfite to a wet pickup of 40%, allowed to stand in the damp state for one hour and then creases are pressed in the trousers by means of a Hoffman press employing a 30 second top stream, a 30 second bake and a ten second vacuum.
  • the creases and dimensional stability of the trousers are found to be durable to several washing cycles in a Kenmore washer, employing commercially available detergents, e.g., Tide brand detergent, in recommended quantities, and employing tumble drying cycles after each wash cycle.
  • the creases and dimensional stability of the trousers are also durable to multiple dry cleaning operations.
  • Example II The procedure of Example I is repeated with the exception that in place of the 70% solution of the prepolymer employed in Example I to effect the external stabilization, a one-shot polyurethane external stabilization technique is employed.
  • the one-shot polyurethane solution is prepared as follows: Sufficient amount of the polypropylene glycol adduct of glycerine employed in Example I to prepare the prepolymer is added to the trichloroethylene pad bath so that pickup of 2.5% based on the dry weight of the fabric of polypropylene glycol adduct is effected.
  • Sufiicient methylene-di-p-phenyl diisocynate is added so that a pickup of 0.5% based on the dry weight of the fabric of the diisocyanate is effected.
  • a quantity of 8% zinc naphthenate solution is added amounting to 3% of the weight of polypropylene glycol adduct and employed diisocyanate.
  • the solution is padded onto the fabric and process thereafter carried out substantially as set forth in Example I.
  • the finished product is found to have a crease and dimensional stability which is durable to several washing cycles employing commercially available detergents, e.g., Tide brand detergent, in recommended quantities, and employing tumble drying cycles after each wash cycle.
  • Example II The procedure of Example II is repeated with the exception that the fabric upon being formulated into a pair of trousers is sprayed instead with an aqueous solution containing 2% by weight sodium bisulfite, 5% urea and 0.2% Deceresol OT.
  • 13 open width externally stabilized fabric is then padded with a solution containing 3% by weight sodium bisulfite and 0.2% 'by weight Deceresol OT.
  • a solution containing 3% by weight sodium bisulfite, 5% by weight urea, and 0.2% by weight Deceresol OT may be employed.
  • the treated fabric is dried at 175 F. and given a light press.
  • the fabric is then fashioned into two pairs of trousers. One pair of trousers is sprayed with water containing 0.2% Deceresol OT to a pickup of about 40% by' weight based on the dry weight of the fabric.
  • creases are pressed into the trousers by means of a Hoffman press, using a cycle of 30 seconds top steam, 30 seconds bake, seconds vacuum, at a steam pressure of 80 p.s.i.
  • the trousers are then dried for minutes in an oven at a temperature of 325 F.
  • the crease and dimensional stability of the fabric is found to be durable to several washing cycles in a Kenmore washer, employing commercially available detergents, e.g., Tide brand detergent, in recommended quantities, and employing tumble drying cycles after each wash cycle.
  • the other pair of trousers is similarly pressed and heated in the oven but without prior wetting with water.
  • the creases so imparted are durable to the effects of a coin-operated dry cleaning unit, but do not withstand the washing operations as well as the other pair of trousers which were wetted before pressing. Similar, though slightly improved, results are obtained when ethylene glycol is substituted for urea and the above procedures are repeated.
  • EXAMPLE VI The procedure set forth in Example IV is repeated with the exception that the externally stabilized fabric is padded with a solution containing 3% by weight sodium bisulfite, 5% urea and 0.2% Deceresol OT.
  • EXAMPLE VII The polyurethane external stabilization process set forth in Example I was again repeated and the externally stabilized fabric again subjected to a scouring, drying and finally a pressing operation.
  • the stabilized fabric is then converted into trousers and the trousers sprayed with an aqueous solution containing 2% by weight sodium bisulfite and 0.2% by weight Deceresol OT (synthetic surfactant agent marketed by American Cyanamid Company) and 5% by weight urea.
  • the spraying is conducted in a fashion so as to produce a pickup of about 40% by weight based on the dry weight of the fabric.
  • the sprayed trouser is then pressed in a Hoffman press.
  • the crease and dimensional stability of the final product is found to be durable to several washing cycles in a Kenmore Washer, employing commercially available detergents, e.g., Tide brand detergent, in recommended quantities, and employing tumble drying cycles after each wash cycle.
  • EXAMPLE VIII An all wool worsted flannel is solvent dry cleaned and is dried free of solvent. The cleaned fabric is then dipped into an emulsion prepared as follows: (a) 4 grams of the polyester reaction product of adipic acid and glycerol is dissolved in 4 milliliters of methylethyl ketone (b) 4'; grams of 2,2 bis(2,3-epoxy-propoxy phenyl) propane was dissolved in 4 milliliters of methylethyl ketone (c) 4 grams of polyamide condensation product of diethylene triamine and dimerized unsaturated fatty acid was dissolved in 4 milliliters of methylether ketone.
  • the 3 solu-' fions of (a), (b), and (c) are then mixed together and the composite solution poured into 37 5 milliliters of water with stirring so as to form an emulsion.
  • the dry cleaned cloth is then dipped into the emulsion and passed through squeeze rolls so as to give a weight increase of 65%.
  • the impregnated fabric is air dried to about 30% moisture and then heated in an oven for 30 minutes at 250 F.
  • a pair of trousers is then prepared from the externally dimensionally stabilized fabric. The trousers are then sprayed with a 6.4% solution of N-propanolamine sulfite to a wet pickup of about 50%.
  • the trousers are then allowed to stand for one hour in the damp state and then creases are pressed in the trousers by means of a Hoffman press employing a 30 second top steam, a 30 second bake and a 10 second vacuum.
  • the trousers are found to have dimensional stability and crease stability after several washing cycles in a Kenmore washer, employing commercially available detergents, e.g., Tide brand detergent, in recommended quantities, and employing tumble drying cycles after each wash cycle.
  • EXAMPLE IX The external stabilization process set forth in Example II was again repeated and the externally stabilized fabric formed into a pair of trousers. The trousers are then sprayed with an aqueous solution containing 2% by weight sodium bisulfite and 0.2% by weight. Deceresol OT. The remainder of the processing operations were conducted substantially in accordance with the process set forth in Example II. The final product was found to have dimensional stability and crease stability afte'r sevenal home laundering cycles in a Kenmore washer, employing commercially available detergents, e.g., Tide brand detergent, in recommended quantities, and employing tumble drying cycles after each wash cycle.
  • commercially available detergents e.g., Tide brand detergent
  • EXAMPLE X A 50% polyester, 50% wool worsted flannel fabric is immersed in a 3.3% aqueous solution of polyaminocaproic acid, diethyl amino ethanol derivative, the specific means of preparation of which is set forth in U.S. Patent No. 2,696,448. Excess pad liquor is removed by passing the fabric through squeeze rollers. The fabric is dried at about C. and then cured at C. for 15 minutes. The externally stabilized fabric is then treated with the reducing agent solution substantially as set forth in Example I.
  • the finished product is found to have dimensional stability and crease stability even after being subjected to several washing cycles in a Kenmore washer, employing commercially available detergents, e.g., Tide brand detergent, in recommended quantities, and employing tumble drying cycles after each wash cycle.
  • the finished product is also found to have dimensional stability and crease stability to multiple dry cleaning operations.
  • Example V The procedure of Example V is repeated with the exception that subsequent to the external stabilization o-peration, the fabric upon being formulated into a pair of trousers is sprayed with an aqueous solution containing 2% by weight sodium bisulfite and 0.2% by weight Deceresol OT, the remaining treatment being conducted substantially as set forth in Example V.
  • the finished product is found to have dimensional and crease stability after having been subjected to several home laundering operations which include the use of commercially available detergents and tumble drying operations.
  • a process for durably setting a fabric containing keratinous fibers in a desired configuration comprising (a) treating said fabric with a monomeric polyisocyanate and a polymeric polyfunctional compound selected from the class consisting of polymeric poly hydroxy compounds, polyesters, polyamides, polyepoxides and reaction products of phenol and alkanol oxides, formaldehyde resins, hydrogenation products of olefin-carbon monoxide copolymers and polyepi- References Cited (b i ii ri g id treated fabric to externall stabilize the UNITED STATES PATENTS fabric, g y 3,098,694 7/1963 Reider s 12s (c) treating the stabilized fabric with a reducing agent, 5 2,710,816 6/1955 f at 8 128 (d) maintaining the reducing agent treated fabric in 3078138 2/1963 Muer et a1 X a desired configuration, and (e) heating the fabric to a temperature sufficient to FOR

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Cited By (11)

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US3797997A (en) * 1969-11-06 1974-03-19 Commw Scient Ind Res Org Method for fixing the shape of textile materials
US3847543A (en) * 1972-11-28 1974-11-12 Deering Milliken Res Corp Reducing shrinkage of textile materials
US3849848A (en) * 1971-05-20 1974-11-26 Iws Nominee Co Ltd Method for the treatment of textile fibres
US3870556A (en) * 1971-04-24 1975-03-11 Bayer Ag Textile finishing compounds
US3986829A (en) * 1972-09-01 1976-10-19 Bayer Aktiengesellschaft Process for felt proofing and dimensionally stabilizing textiles made of fibers which contain keratin
US4071313A (en) * 1975-12-05 1978-01-31 Commonwealth Scientific And Industrial Research Organization Polyurea polycarbamoyl sulphonates
US4289827A (en) * 1979-03-06 1981-09-15 Bayer Aktiengesellschaft Moisture hardening one-component lacquers and a process for coating leather
US5942486A (en) * 1997-02-28 1999-08-24 The Procter & Gamble Company Dryer-activated laundry additive compositions with color care agents
EP0863249A3 (de) * 1997-03-04 1999-10-06 Ciba Spezialitätenchemie Pfersee GmbH Verfahren zur Behandlung von Wolle enthaltenden Geweben, insbesondere Kleidungsstücken
US5998359A (en) * 1997-02-28 1999-12-07 The Procter & Gamble Company Rinse added laundry additive compositions having color care agents
US11230807B2 (en) 2014-04-19 2022-01-25 52 Launch Llc Compositions and methods for treating keratinous material

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Publication number Priority date Publication date Assignee Title
AU427112B2 (en) * 1967-09-22 1972-09-13 Rank Xerox Limited Electrostatographic imaging
DE2243068A1 (de) * 1972-09-01 1974-03-07 Bayer Ag Verfahren zur veredlung von textilgutmaterialien aus keratinhaltigen fasern
ITMI20030201A1 (it) * 2003-02-06 2004-08-07 Massimo Guarducci S R L Metodo per prevenire la restringibilita' dei tessuti
WO2014120100A1 (en) * 2013-01-29 2014-08-07 Güven Boya Apre Ve Dokuma Fabri̇kalari Anoni̇m Şi̇rketi̇ Production method providing size stability of wool and wool blend fabrics

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US2508713A (en) * 1946-10-07 1950-05-23 Harris Res Lab Treatment of keratinous material
US2524042A (en) * 1948-04-20 1950-10-03 Croston Clarence Bradford Curing prolamine fibers with aldehyde in liquid organic medium
US2678287A (en) * 1950-01-24 1954-05-11 E I Du Pont De Nemoursm & Comp Shrinkproofing wool with substituted polymers of ethylene
US2689194A (en) * 1952-02-18 1954-09-14 Sayles Finishing Plants Inc Finishing process and fabric
US3040002A (en) * 1957-06-27 1962-06-19 Exxon Research Engineering Co Isocyanates
US2933409A (en) * 1958-08-14 1960-04-19 Charles H Binkley Method for imparting permanent deformation to textiles
US3098694A (en) * 1960-07-11 1963-07-23 Drew Chem Corp Continuous treatment of wool to shrinkproof and sensitize the same
US3084018A (en) * 1961-03-29 1963-04-02 Robert E Whitfield Shrinkproofing wool with polyurethanes
US3151439A (en) * 1962-07-09 1964-10-06 Deering Milliken Res Corp Process for making elastic keratinous yarns

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3797997A (en) * 1969-11-06 1974-03-19 Commw Scient Ind Res Org Method for fixing the shape of textile materials
US3870556A (en) * 1971-04-24 1975-03-11 Bayer Ag Textile finishing compounds
US3849848A (en) * 1971-05-20 1974-11-26 Iws Nominee Co Ltd Method for the treatment of textile fibres
US3986829A (en) * 1972-09-01 1976-10-19 Bayer Aktiengesellschaft Process for felt proofing and dimensionally stabilizing textiles made of fibers which contain keratin
US3847543A (en) * 1972-11-28 1974-11-12 Deering Milliken Res Corp Reducing shrinkage of textile materials
US4071313A (en) * 1975-12-05 1978-01-31 Commonwealth Scientific And Industrial Research Organization Polyurea polycarbamoyl sulphonates
US4289827A (en) * 1979-03-06 1981-09-15 Bayer Aktiengesellschaft Moisture hardening one-component lacquers and a process for coating leather
US5942486A (en) * 1997-02-28 1999-08-24 The Procter & Gamble Company Dryer-activated laundry additive compositions with color care agents
US5998359A (en) * 1997-02-28 1999-12-07 The Procter & Gamble Company Rinse added laundry additive compositions having color care agents
EP0863249A3 (de) * 1997-03-04 1999-10-06 Ciba Spezialitätenchemie Pfersee GmbH Verfahren zur Behandlung von Wolle enthaltenden Geweben, insbesondere Kleidungsstücken
US6056788A (en) * 1997-03-04 2000-05-02 Ciba Specialty Chemicals Corporation Processes for creasing moist wool fabrics
US11230807B2 (en) 2014-04-19 2022-01-25 52 Launch Llc Compositions and methods for treating keratinous material

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FR1513989A (fr) 1968-02-16
BE695453A (en:Method) 1967-09-14
LU53191A1 (en:Method) 1967-05-16

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