US2752269A - Treatment of textile materials - Google Patents

Treatment of textile materials Download PDF

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US2752269A
US2752269A US259504A US25950451A US2752269A US 2752269 A US2752269 A US 2752269A US 259504 A US259504 A US 259504A US 25950451 A US25950451 A US 25950451A US 2752269 A US2752269 A US 2752269A
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acid
fabric
parts
ether
fabrics
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Fred E Condo
Carl W Schroeder
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Shell Development Co
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Shell Development Co
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Priority to NLAANVRAGE7411923,A priority Critical patent/NL174182B/xx
Priority to BE515900D priority patent/BE515900A/xx
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Priority to US259504A priority patent/US2752269A/en
Priority to GB30258/52A priority patent/GB732573A/en
Priority to DEN6423A priority patent/DE1024049B/de
Priority to FR1071905D priority patent/FR1071905A/fr
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates 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
    • C08G59/18—Macromolecules 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
    • C08G59/40—Macromolecules 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
    • C08G59/62—Alcohols or phenols
    • C08G59/625—Hydroxyacids
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/55—Epoxy resins
    • 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
    • Y10S8/08—Oxirane

Definitions

  • This invention relates to the treatment of textile materials. More particularly, the invention relates to a method for preparing textile fabrics that have improved wrinkle and shrink resistance and other improved properties.
  • the invention provides a novel process for preparing crease resistant and shrink resistant, resilient textile fabrics having improved washability and no chlorine retention which comprises applying to the textile fabric a solution containing a polyepoxide and subsequently curing the polyepoxide within the fibers of the fabric in the presence of a curing agent.
  • the invention further provides improved fabrics prepared by the aforedescribed process.
  • the fabrics treated in the above-described manner have no ability to retain chlorine and the coated fabrics may be bleached or otherwise exposed to chlorine without danger of being discolored, charred or weakened during subsequent heat treatments.
  • the fabrics have been found to have improved washability and can be washed numerous times without danger of losing any substantial amount of the polyepoxide resin.
  • the polyepoxides used in treating the fabrics include those organic compounds having at least two epoxy groups per molecule.
  • the po-lyepoxides may be saturated or unsaturated, aliphatic, cycloaliphatic, aromatic or heterocyclic and may be substituted if desired with noninterfering substituents, such as hydroxyl groups, ether radicals, and the like. They may also be monomeric or polymeric.
  • epoxy equivalency refers to the average number of epoxy groups contained in the average molecule. This value is obtained by dividing the average molecular weight of the polyepoxide by the epoxide equivalent weight. The epoxide equivalent weight is determined by heating a one-gram sample of the polyepoxide with an excess of pyridinium chloride dissolved in pyridine. The excess pyridiniurn chloride is then back titrated with 0.1 N sodium hydroxide to phenolphthalein end point. The epoxide value is calculated by considering one HCl as equivalent to one epoxide group. This method is used ot obtain all epoxide values reported herein.
  • the epoxy equivalency will be integers, such as 2, 3, 4, and the like.
  • many of the materials may contain some of the monomeric monoepoxides or have some of their epoxy groups hydrated or otherwise reacted and/or contain macromolecules of somewhat different molecular weight so the epoxy equivalency may be quite low and containing fractional values.
  • the polymeric material may, for example, have an epoxy equivalency of 1.5, 1.8, 2.5 and the like.
  • the polyepoxides may be exemplified by the following: 1,4 bis(2,3 epoxypropoxy)benzene, 1,3 bis(2,3- epoxypropoxy)benzene, 4,4 bis(2,3 epoxypropoxy)- diphenyl ether, 1,8 bis(2,3 epoxypropoxy)octane, 1,4 bis(2,3 epoxypropoxy)cyclohexane, 4,4 bis(2 hydroxy 3,4 epoxybutoxy) diphenyldimethylmethane, 1,3 bis(4,5 epoxypentoxy) 5 chlorobenzene, 1,4- bis(3,4 epoxybutoxy) 2 chlorocyclo-hexane, diglycidyl thioether, diglycidyl ether, ethylene glycol diglycidyl ether, resorcinol diglycidyl ether, l,2,5,6-diepoxyhexyne, 1,2,5,6-
  • polyether F which is substantially 2,2-bis(2,3-epoxypropoxyphenyl)propane is obtained by reacting bis-phenol (2,2-bis(4-hydroxyphenyl)propane) with an excess of epichlorohydrin.
  • polyhydric phenols that can be used for this purpose include resorcinol, catechol, hydroquinone, methy resorcinol, or polynuclear phenols, such as 2,2-bis(4-hydroxyphenyl)butane, 4,4 dihydroxybenzophenone, bis(4 hydroxyphenyl)ethane, and 1,5-dihydronaphthalene.
  • the halogen-containing epoxides may be further exemplified by 3-chloro-1,2-epoxybutane, 3 bromo l,3 epoxyhexane, 3-chloro-1,2-epoxyoctane, and the like.
  • polyepoxides comprises the polyepoxy polyethers obtained by reacting, preferably in the presence of an acid-acting compound, such as hydrofluoric acid, one of the aforedescribed halogen-containing epoxides with a polyhydric alcohol, and subsequently treating the resulting product with an alkaline component.
  • an acid-acting compound such as hydrofluoric acid
  • Polyhydric alcohols that may be used for this purpose include glycerol, propylene glycol, ethylene glycol, diethylene glycol, butylene glycol, hexanetriol, sorbitol, mannitol, pentanetriol, pentaerythritol, diand tripentaerythritol, polyglycerol, dulcitol, inositol, carbohydrates, methyltrimethylolpropane, 2,6-octanediol, tetrahydroxycyclohexane, 2-ethylhexanetriol-1,2,6, glycerol methyl ether, glycerol allyl ether, polyvinyl alcohol and polyallyl alcohol, and mixtures thereof.
  • Such polyepoxides may be exemplified by glycerol triglycidyl ether, mannitol tetraglycidyl ether, pentaerythritol tetraglycidyl ether and sorbitol tetraglycidyl ether.
  • polyepoxides include the polyepoxypolyhydroxy polyethers obtained by reacting, preferably in an alkaline medium, a polyhydric alcohol or polyhydric phenol with a polyepoxide, such as the reaction product of glycerol and bis(2,3-epoxypropyl) ether, the reaction product of sorbitol and bis(2,3-epoxy-2-methylpropyl)ether, the reaction product of pentaerythritol and 1,2-epoxy- 4,5-epoxypentane, and the reaction product of bis-phenol and bis(2,3-epoxy-2-methylpropyl)ether, the reaction product of resorcinol and bis(2,3-epoxypropyl)ether, and the reaction product of catechol and bis(2,3-epoxypropyl)ether.
  • a polyepoxide such as the reaction product of glycerol and bis(2,3-epoxypropyl) ether, the reaction product of sorbi
  • a group of polymeric-type polyepoxides comprises the hydroxy-substituted polyepoxy polyethers obtained by reacting, preferably in an alkaline medium, a slight excess, e. g., .5 to 3 mol excess, of a halogen-containing epoxide as described above, with any of the aforedescribed polyhydric phenols, such as resorcinol, catechol, bis-phenol, bis(2,2'-dihydroxy-dinaphthyl)methane, and the like.
  • polymeric polyepoxides include the polymers and copolymers of the epoxy-containing monomers possessing at least one polymerizable ethylenic linkage.
  • this type of monomer is polymerized in the substantial absence of alkaline or acidic catalysts, such as in the presence of heat, oxygen, peroxy compounds, actinic light, and the like, they undergo addition polymerization at the multiple bond leaving the epoxy group unaffected.
  • These monomers may be polymerized with themselves or with other ethylenically unsaturated -monorners, such as styrene, vinyl acetate, methacrylonitrile, acrylonitrile, vinyl chloride, vinylidene chloride, methyl acrylate, methyl methacrylate, diallyl phthalate, vinyl allyl phthalate, divinyl adipate, chloroallyl acetate, and vinyl methallyl pimelate.
  • ethylenically unsaturated -monorners such as styrene, vinyl acetate, methacrylonitrile, acrylonitrile, vinyl chloride, vinylidene chloride, methyl acrylate, methyl methacrylate, diallyl phthalate, vinyl allyl phthalate, divinyl adipate, chloroallyl acetate, and vinyl methallyl pimelate.
  • polystyrene resins examples include poly(allyl 2,3-epoxypropyl ether), allyl 2,3-epoxypropyl etherstyrene copolymer, methallyl 3,4-epoxybutyl ether-allyl benzoate copolymer, poly(vinyl 2,3-expoxypropyl)ether, allyl glycidyl ether-vinyl acetate copolymer and poly(4- glycidyloxystyrene)
  • Preferred polyepoxides to be used in treating the textile fabrics according to the process of the present invention comprise the members of the group consisting of diglycidyl ether, diglycidyl thioether, monomeric aliphatic polyepoxides containing a plurality of glycidyl radicals joined through oxygen or sulfur ether linkages to aliphatic hydrocarbon radicals, monomeric aromatic polyepoxides containing a plurality of glycidyl
  • the polymers and copolymers of the aliphatic epoxycontaining monomers are the polymers and copolymers of the aliphatic epoxycontaining monomers, and more particularly the glycidyl ethers of unsaturated aliphatic alcohols, such as allyl 1,3-glycidyl ether, vinyl 2,3-glycidyl ether, allyl 2,3- glycidyl ether, crotyl 2,3-epoxybutyl ether, 2-methyl-2- hexenyl 2,3-glycidyl ether, and the like.
  • unsaturated aliphatic alcohols such as allyl 1,3-glycidyl ether, vinyl 2,3-glycidyl ether, allyl 2,3- glycidyl ether, crotyl 2,3-epoxybutyl ether, 2-methyl-2- hexenyl 2,3-glycidyl ether, and the like.
  • These polymers are preferably prepared by heating the monomer or monomers in bulk or in the presence of an inert solvent such as benzene in the presence of air or a peroxy catalyst, such as ditertiarybutyl peroxide, at temperatures ranging generally from 75 C. to 200 C.
  • an inert solvent such as benzene
  • a peroxy catalyst such as ditertiarybutyl peroxide
  • polymers of this type may be illustrated by the following example showing the preparation of poly(allyl glycidyl ether).
  • Particularly preferred members of the above-described group comprise the polymers of the Z-alkenyl glycidyl ethers having a molecular weight between 300 and 1000 and an epoxy equivalency greater than 1.0, and preferably between 1.2 and 6.0.
  • polyglycidyl polyethers of polyhydric alcohols obtained by reacting the polyhydric alcohol With epichlorohydrin, preferably in the presence of 031% to 5% by weight of an acid-acting compound, such as boron trifluoride, hydrofluoric acid, stannic chloride or 'stannic acid.
  • an acid-acting compound such as boron trifluoride, hydrofluoric acid, stannic chloride or 'stannic acid.
  • This reaction is effected at about 50 C. to C. with the proportions of reactants being such that there is about one mole of epichlorohydrin for every equivalent of hydroxyl group in the polyhydric alcohol.
  • the resulting chlorohydrin ether is then dehydrochlorinated by heating at about 50 C. to 125 C. with. a small, e. g., 10% stoichiometrical excess of a base, such as sodium aluminate.
  • Particularly preferred members of this group comprise the glycidyl polyethers of aliphatic polyhydric alcohols containing from 2 to 10 carbon atoms and having from 2 to 6 hydroxyl groups and more preferably the alkane polyols containing from 2 to 8 carbon atoms and having from 2 to 6 hydroxyl groups.
  • Such products preferably have an epoxy equivalency greater than 1.0, and still more preferably between 1.1 and 4 and a molecular weight between 300 and 1000.
  • the monomeric and polymeric glycidyl polyethers of dihydric phenols obtained by reacting epichlorohydrin with a dihydric phenol in an alkaline medium.
  • the monomeric products of this type may be represented by the general formula wherein R represents a divalent hydrocarbon radical of the dihydric phenol.
  • the polymeric products will generally not be a single simple molecule but will be a complex mixture of glycidyl polyethers of the general formula wherein R is a divalent hydrocarbon radical of the dihydric phenol and n is an integer of the series 0, 1, 2, 3, etc.
  • n is an integer
  • the fact that the obtained polyether is a mixture of compounds causes the determined value of n to be an average which is not necessarily zero or a whole number.
  • the polyethers may in some cases contain a very small :amount of material with one or both of the terminal gly- .cidyl radicals in hydrated form.
  • the aforedescribed preferred glycidyl polyethers of the 'dihydric phenols may be prepared by reacting the required proportions of the dihydric phenol and the epichlorohydrin in an alkaline medium.
  • the desired alkalinity is obtained by adding basic substances, such as sodium or potassium hydroxide, preferably in stoichiometric excess to the epichlorohydrin.
  • the reaction is preferably accomplished at temperatures within the range of from 50 C. to 150 'C. The heating is continued for several hours to effect the reaction and the product is then washed free of salt and base.
  • the benzene was then removed to yield a viscous liquid having a viscosity of about 150 poi'ses at 25 C. and a molecular weight of about 350 (measured ebullioscopically in ethylene dichloride).
  • the product had an epoxy value of 0.50 eq./100 g., and an epoxy equivalency of 1.75.
  • this product will be referred to hereinafter as Polyether C.
  • the product was an extremely viscous semisolid having a melting point of 27 C. by Durrans mercury method and a molecular weight of 483.
  • this product will be referred to as Polyether D.
  • Particularly preferred members of the above-described group are the glycidyl polyethers of the dihydric phenols, and especially 2,2-bis(4-hydroxyphenyl)propane, having an epoxy equivalency between 1J1 and 2.0 and a molecular weight between 300 and 900. Particularly preferred are those having Durrans mercury method softening point below about 60 C.
  • the polyepoxides are preferably applied to the fabric in the form of a solution or dispersion in order to insure a proper distribution of the materials throughout the fibers of the fabric.
  • Any liquid medium such as water, aqueous emulsions, volatile or relatively volatile solvents, may be used in the preparation of these solutions.
  • the liquid medium employed with the polyepoxides should have no pronounced solvent action on the fibers of the fabric being treated, though the use of a medium having a slight solvent action or latent solvent or swelling action upon the fibers is not excluded and may, in fact, be advantageous.
  • Suitable solvents include ethyl alcohol, butyl alcohol, isopropyl alcohol, acetone, dioxane, diacetone alcohol, esters, ethers and ether esters of glycol and glycerol, ethylene dichloride, benzene, toluene, and the like, and mixtures thereof.
  • the more soluble polyepoxides are preferably employed in a water solution or a solution made up of water and other miscible components, such as the lower aliphatic alcohols, such as ethyl alcohol, isopropyl alcohol, methanol, and the like.
  • Particularly preferred mediums of this type comprise water-alcohol mixtures having a weight ratio varying from 3:1 to 1:5.
  • the less soluble polyepoxides such as the viscous liquid to solid glycidyl polyethers of the dihydric phenols described above, are preferably employed in a volatile solvent or in an aqueous emulsion.
  • Emulsifying agents employed for this purpose are preferably those that are free of nitrogen and strong acidic groups, such as the monooleate of sorbitan polyoxyethylene, the trioleate of sorbitan polyoxyethylene, sorbitan tristearate, sorbitan monolaurate, polyoxyethylene ethers of alkylphenols, carboxymethylcellulose, starch, gum arabic, aryl and alkylated aryl sulfonates, such as cetyl sulfonate, oleyl sulfonate, sulfonated mineral oils, and the like, and mixtures thereof.
  • the emulsifying agents are generally employed in amounts varying from 0.1% to 10% by weight and more preferably from 1% to by weight.
  • the amount of the polyepoxide in the impregnating solution may vary over a considerable range depending chiefly on the amount of resin to be deposited on the fabric and this in turn will depend on the number of applications and the pick-up allowed per application.
  • a concentration ranging from 3% to 25 by Weight will ordinarily suffice. If less than 80% pick-up is permitted, the concentration may in some cases go as high as 30% to 50%.
  • the hardening or curing agents may be added to the polyepoxide solution before it is applied to the fabric or it may be applied by spraying or other suitable methods to the fabric after it has been impregnated with the polyepoxide.
  • the curing agents are preferably added to the solution before it is applied to the fabric.
  • Preferred curing agents to be used include the acid and acid-acting curing agents, such as the organic and inorganic acids and anhydrides as citric acid, acetic acid, acetic acid anhydride, butyric acid, caproic acid, phthalic acid, phthalic acid anhydride, tartaric acid, aconitic acid, oxalic acid, succinic acid, succinic acid anhydride, lactic acid, maleic acid, maleic acid anhydride, fumaric acid, glutaconic acid, l,2,4-butanetricarboxylic acid, isophthalic acid, terephthalic acid, malonic acid, l,1,5-pentanetricarboxylic acid, acetoacetic acid, naphthalic acid, trimellitic acid, phosphoric acid, boric acid, sulfonic acid, phosphinic acid, perchloric acid, persulfuric acid, p-toluenesulfonic acid, ethan
  • the boron-triiluoride complexes may also used as hardening agents.
  • the amino compounds such as trietlryiarnine, ethylene diamine, and diethylene triamine may also be used but are less preferred.
  • Particularly preferred curing agents comprise the organic carboxylic acids and inorganic acids and their correspo. anhydrides, and more preferably the organic monocarboxylic acids and polycarboxylic acids containing from 2 to 12 carbon atoms, and their respec tive anhydrides, and the inorganic acids containing sulfur, phosphorous or boron, such as boric acid, phosphoric acid and sulfonic acid.
  • the amount of the curing agent to be utilized will vary over a wide range depending upon the polyepoxide selected, the method of cure, etc.
  • the organic acids and acid anhydrides are preferably added in an amount varying 0.1 to 2 times the stoichiometric amount, the stoichiometric quantity in this case being that amount sufiicient to furnish one carboxyl group for every epoxide group.
  • Particularly amounts of organic acids and acid anhydrides vary from 0.2 to 1.5 times the stoichiometric amount.
  • the inorganic acids are preferably employed in amounts varying from 0.5% to 20% by weight of the polyepoxide, and more preferably from 2% to 10% by weight.
  • the boron-trifluoride complexes are generally employed in amounts varying from 0.25% to 5% and more preferably from 1% to 3% by weight.
  • the solutions employed to treat the textiles may also contain plasticizers to improve their flexibility, though these should not be present in such proportions as to render the finished materials soft or sticky at temperature and humidities to which they would be exposed. It is found, however, that the substances employed in the present invention yield products which are sufliciently flexible for most purposes without the use of plasticizers.
  • the compositions may also contain natural resins, e.
  • shellac shellac, rosin, and other natural resins and synthetic or semi-synthetic resins, e. g., ester gum, polyhydroxypolybasic alkyd resins, phenolaldehyde and urea-aldehyde resins.
  • Textile softening agents and particularly those of the cationic-type as stearamidoethyl diethyl methyl quaternary ammonium methyl sulphate, trimethyl ammonium methyl sulphate of monostearylmetaphenylenediamine, s-di (1- (2-palmitamidoethyl)) urea monoacetate, palmityl amine hydrochloride, and the like, and mixtures thereof, may also be added in varying amounts to improve the feel of the treated fabrics.
  • the application of the solution containing the polyepoxide to the textile fabric may be eifected in any suitable manner, the method selected depending upon the results desired. If it is desired to apply the solution only to one surface of the material, as, for example, when it is desired to treat the back only of a fabric having a face of artificial or natural silk and a cotton back, the application may be effected by spraying or by means of rollers, or the composition may be spread upon the surface by means of a doctor blade. When, however, it is desired to coat both surfaces of the material, or if the material is to be thoroughly impregnated With it, the fabrics may be simply dipped in the solution or run through conventional-type padding rollers. The solutions may also be applied locally to the material, for example, by means of printing rollers or by stencilling.
  • the amount of the polyepoxides to be deposited on the fabric will vary over a wide range depending upon the degree of wrinkle-resistance and shrink-resistance desired in the finished material. if the fabric is to have a soft feel, such as that intended for use for dresses, shirts, etc., the amount of polyepoxide deposited will generally vary from 3% to 20% by weight of the fabric. If stiffer materials are required such as for shoe fabrics, draperies, etc. still higher amounts of resins, such as of the order of 25% to 50% by weight may be deposited.
  • the solution can be applied again or as many times as desired in order to bring the amount of the polyepoxide up to the desired level.
  • impregnated 010th was then dried at r 15 m ndrying periods of from 5 to inut h ld b fli utes and cured at 160 C. for 5 minutes.
  • the finished cient. 15 product was washed in a 0.13% solution of Ivory flakes
  • the dried fabric is then exposed to relatively high temand 0.065% Na2CO3 solution at 70 C. for 12 minutes peratures to accelerate the cure of the polyepoxides, and then rinsed three times in warm water to remove any Temperatures used for this purpose generally range from lu l mat rials. 100 C. to 200 C., and more preferably from 100 C.
  • the cloth treated in the above-described manner was to 150 C.
  • the process of the invention may be applied to the treatment of cellulosic fabrics as cotton fabric and fabric made 11p of regenerated cellulose (rayon) such as obtained by the viscose, cuprammonium or nitrocellulose process. While the invention has been particularly described with relation to the treatment of woven fabrics, it may also be applied to other materials, for example, knitted or netted fabrics.
  • regenerated cellulose rayon
  • the materials treated according to the process of the invention will have excellent wrinkle and shrink resistance as well as good resiliency and flexibility and may be used for a wide variety of important applications.
  • the woven cotton, rayon and wool fabrics, both colored and white, containing conventional amounts of resin, e. g., from 3% to 25% by weight, may be used, for example, in the preparation of soft goods, such as dresses, shirts, coats, sheets, handkerchiefs, and the like, while the fabrics containing much larger amounts of the resin, 6. g., 25% to 50% may be used in other applications demanding more crispness and fullness such as the preparation of rugs, carpets, plushes, drapes, upholsteries, shoe fabrics, and the like.
  • the wrinkle recovery values reported in the examples were determined by the Monsanto wrinkle recovery method, and the tear strength values were determined by the Trapezoid methodASTMD-3949. All tests were carried out at 50% relative humidity and 78 F.
  • Example II (a) About 100 parts of poly(al1yl glycidyl ether) (Polymer A described above) was. dissolved in a solution I 11' made up of 140 parts of isopropyl alcohol and 420 parts of water, and then 40 parts of citric acid was added to the resulting solution.
  • Cotton print cloth (80 x 80 count) was then impregnated with this solution as shown in. Example I.
  • the impregnated cloth was dried at 60 C. for 15 minutes and cured at 160 C. for 5 minutes. It was then washed as in Example I to remove any soluble material.
  • the cloth treated in the above-described manner had a 61% increase in wrinkle recovery.
  • Example III A series of impregnating solutions containing Polyether B and a variety of different curing agents was prepared in the following manner: 100 parts of the polyether was dissolved in a solution made upof 140 parts of isopropyl alcohol and 420 parts of water and then the curing agent was added thereto.
  • Sheets of cotton print cloth were then impregnated with the individual solutions as indicated in Example I to give a 56% resin pick-up.
  • the sheets were dried at 60 C. for 5 to 15 minutes and then cured at160 C. for 5 minutes.
  • Example IV In this experiment, the Polyether B-citric acid impregnating solution prepared in Example I and the Polymer A-citric acid solution shown in Example II were used to.
  • the rayon cloth treated in the above-described manner was quitesoft andhad increased wrinkle resistance, good washability and excellent shrink resistance.
  • the wrinkle recovery is shown in the following table in comparison to an unp'added sheet and a similar sheet padded with an urea-formaldehyde resin.
  • Wrinkle Recovery Example V This example illustrates the increase in tear strength that is obtained by using many of the polyepoxides described in the foregoing specification.
  • Cotton print cloth was then treated with the abovedescribed solution as shown in Example 1, dried at 60 C. and then cured at C. for 5 minutes.
  • the finished sheets had a 14% increase in wrinkle resistance and a 14.3% increase in tear strength.
  • the sheets also had improved washability and no chlorine retention.
  • Example VI About 100 parts of diglycidyl ether of ethylene glycol having an epoxy value of 1.039 eq./ 100 g. was dissolved in a solution made up of 140 parts of isopropyl alcohol and 420 parts of water, and then about 40 parts of citric acid was added.
  • Cotton print cloth treated with the above-described solution as indicated in Example V was soft and had increased wrinkle resistance, improved washability and no chlorine retention.
  • Example VII About 100'parts of a glycidyl polyether of bis-phenol having an epoxy equivalency of 1.75 and a molecular weight of about 350 (Polyether C produced above) was combined with 30 parts of citric acid and 10 parts of an emulsifying agent comprising a copolymer of ethylene oxide and propylene oxide (Pluronic F-68). This mixture was warmed to form a solution of the components and then cooled. Water was then added dropwise with gentle paddling unit the emulsion inverted. A further quantity of water was then added rapidly to form a solution having a 10% resin concentration.
  • an emulsifying agent comprising a copolymer of ethylene oxide and propylene oxide
  • Cotton print cloth described above was impregnated with the above-described emulsion by means of the Butterworth 3-roll laboratory padder.
  • the impregnated cloth was dried at 60 C. for 15 minutes and cured at 160 CI for 5 minutes.
  • the resulting fabric had an increase in wrinkle resistance of 23.5% and a 35% decrease in tear strength.
  • Example VIII About 200 parts of a glycidyl polyether of bis-phenol having an epoxy equivalency of 1.9 and a molecular weight of 483 (Polyether'D produced above) is stirred with 2 parts of sorbitan monoleate (Span 20) and this mixture is then added to 200 parts of a 1% solution of a monooleate of sorbitan polyoxyethylene (Tween 80) and the resulting mixture stirred at full speed with the B'rookfield' 12,000 R. P. M. stirrer. 20 parts of citric acid isthen added to the resulting emulsion.
  • Cotton print cloth treated with the above-described emulsion as in the preceding example is soft and has increased wrinkle resistance, improved washability and low non-chlorine retention.
  • Example IX Crease resistant fabrics which were unusually soft and had a pleasant feed were obtained by the following procedure.
  • Aerotex Softener H (a mixed cationic and anionic long chain derivative) was then added to separate portions of the above-described solution in proportions indicated in the table below.
  • the treated sheets were very soft and had a pleasant feel but still had very good crease and shrink resistance.
  • the wrinkle recovery values are shown in the following table.
  • a process for producing crease resistant and wrinkle resistant textile fabrics containing substantially all cellulosic material of the group consisting of cotton and rayon having a soft feel and improved resistance to washing and low chlorine retention which comprises impregnating the textile fabric with a Water-alcohol solution containing a saturated polyglycidyl ether of a polyhydric alcohol having an epoxy equivalency greater than 1.0 and a molecular weight between 300 and 900 and an acid curing agent, drying the composition for a short period, and then heating the composition at a temperature between 50 C. and 200 C. to cure the polyepoxide within the fibers of the said fabric.
  • a process for producing crease resistant and shrink resistant textile fabrics containing substantially all cellulosic material of the group consisting of cotton and rayon having a soft feel and improved washability and low chlorine retention which comprises impregnating the textile fabrics with an aqueous emulsion containing a saturated polyglycidyl ether of a polyhydric alcohol having an epoxy equivalency greater than 1.0, and an acid curing agent, and then heating the composition at a temperature between 50 C. and 200 C. to cure the polycpoxide within the fabric fibers.
  • a process for producing crease-resistant and shrinkresistant cellulosic textile fabrics containing substantially all cotton which comprises impregnating the textile fabric with an aqueous dispersion containing a glycidyl polyether of glycerol, having an epoxy equivalency of about 2 to 3 and a molecular weight between 300 and 900, and a curing agent, and then heating the treated fabric to cure the glycidyl polyether of glycerol within the treated fabric.
  • a process for producing crease-resistant and shrinkresistant textile fabrics containing substantially all cotton which comprises impregnating the textile fabric with an aqueous emulsion containing a saturated polyepoxy-containing dehydrochlorinated reaction product of an aliphatic polyhydric alcohol and epichlorohydrin which reaction product has an epoxy equivalency greater than 1.0, and a curing agent, and then heating the resulting treated fabric to cure the polyepoxy-containing reaction product within the treated fabric.
  • a process for treating textile materials containing substantially all cellulosic material selected from the group consisting of cotton and rayon to make them crease-resistant and shrink resistant without affecting feel and chlorine-retentive properties which comprises impregnating the textile material with an aqueous medium containing a saturated polyglycidyl ether of a polyhydric alcohol having an epoxy equivalency greater than 1.0, and a curing agent, and then heating the treated textile material to cure the polyglycidyl ether within the treated textile material.
  • a process as in claim 9 wherein the polyhydric alcohol is glycerol.
  • a process as in claim 9 wherein the polyhydric alcohol is diethylene glycol.
  • a process as in claim 9 wherein the curing agent is an acid-acting curing agent.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
US259504A 1951-12-01 1951-12-01 Treatment of textile materials Expired - Lifetime US2752269A (en)

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NLAANVRAGE7411923,A NL174182B (nl) 1951-12-01 Brander.
BE515900D BE515900A (en)) 1951-12-01
US259504A US2752269A (en) 1951-12-01 1951-12-01 Treatment of textile materials
GB30258/52A GB732573A (en) 1951-12-01 1952-11-28 Treatment of textile materials for improving crease and shrink resistance
DEN6423A DE1024049B (de) 1951-12-01 1952-11-29 Verfahren zum Knitterfest- und Schrumpffestmachen von Textilien
FR1071905D FR1071905A (fr) 1951-12-01 1952-12-01 Procédé pour le traitement de matières textiles

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US2794754A (en) * 1956-04-30 1957-06-04 Shell Dev Treatment of textile materials
US2826514A (en) * 1955-11-17 1958-03-11 Shell Dev Treatment of textile materials and composition therefor
US2829071A (en) * 1954-04-26 1958-04-01 Shell Dev Treatment of wool containing textiles
US2841595A (en) * 1955-01-31 1958-07-01 Shell Dev Process for manufacture of glycidyl ethers of polyhydric phenols
US2848435A (en) * 1955-03-28 1958-08-19 Shell Dev Process for the manufacture of epoxy resins
US2869970A (en) * 1957-04-11 1959-01-20 Edward M Filachione Tanning with epoxy resins
US2886472A (en) * 1956-04-27 1959-05-12 Shell Dev Treatment of textile materials
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
US2913356A (en) * 1955-06-28 1959-11-17 Shell Dev Preparation of paper having improved wet strength
US2928811A (en) * 1957-11-18 1960-03-15 Devoe & Raynolds Co Epoxide resin-amide compositions
US2928794A (en) * 1956-12-05 1960-03-15 Devoe & Raynolds Co Inc Curing of polyepoxides
US2928808A (en) * 1956-12-10 1960-03-15 Devoe & Raynolds Co Inc Curing of polyepoxides
US2928803A (en) * 1956-10-05 1960-03-15 Devoe & Raynolds Co Inc Curing of polyepoxides
US2928810A (en) * 1957-11-15 1960-03-15 Devoe & Raynolds Co Aliphatic alcohol-epoxide resin compositions
US3000690A (en) * 1956-02-06 1961-09-19 Rohm & Haas New polymers of unsaturated glycidyl ethers and methods for producing them
US3019076A (en) * 1958-07-22 1962-01-30 Jr Clay E Pardo Treatment of textiles with polyepoxides and polyamides
US3024080A (en) * 1957-10-14 1962-03-06 Rohm & Haas 2, 6-dioxaspiro (3, 3)heptane treated cellulose fabric and the production thereof
US3026216A (en) * 1959-10-05 1962-03-20 Union Carbide Corp Treatment of textile fabrics with methylglycidyl ethers
US3036041A (en) * 1957-12-23 1962-05-22 Richardson Co Reaction products of epoxylated compositions and process
US3043813A (en) * 1958-10-03 1962-07-10 Union Carbide Corp Polymer of alkenyl epoxycyclopentyl ethers
US3069311A (en) * 1962-03-28 1962-12-18 Hercules Powder Co Ltd Paper manufacture
US3073799A (en) * 1958-01-20 1963-01-15 Gen Electric Resin compositions and their preparation
US3073662A (en) * 1963-01-15 Process for the production of fast dye-
US3084073A (en) * 1959-12-10 1963-04-02 Rohm & Haas Copolymers of alkyl acrylate, methoxymethyl vinyl sulfide, comonomer containing functional groups, and coating compositions thereof
US3097050A (en) * 1959-12-28 1963-07-09 Rohm & Haas Process of creaseproofing cellulose fabrics with 2, 6-dioxaspiro (3, 3) heaptane and ormaldehyde and fabrics produced thereby
US3128147A (en) * 1959-09-30 1964-04-07 Courtaulds Ltd Process for treating polynosic fibers and products obtained thereby
US3131083A (en) * 1960-03-25 1964-04-28 Standard Packaging Corp Method of impregnating card stock
US3150190A (en) * 1960-02-18 1964-09-22 Quaker Chem Corp Acetal condensation products and their preparation
US3196117A (en) * 1958-06-19 1965-07-20 Archer Daniels Midland Co Intermolecular alkyd-epoxy complexes
US3206328A (en) * 1960-03-01 1965-09-14 American Cyanamid Co Process for imparting anti-static properties to hydrophobic textile materials and product thereof
US3228920A (en) * 1960-05-12 1966-01-11 Metal Recovery Systems Chelating resins and method of preparation
US3293073A (en) * 1964-02-12 1966-12-20 Union Carbide Corp Process for imparting wash and wear properties to cellulose-containing textile fabric and resulting product
US3293071A (en) * 1964-02-14 1966-12-20 Union Carbide Corp Process for treating cellulosic textile material
US3313796A (en) * 1964-02-24 1967-04-11 Monsanto Co Process for improving the antistatic properties of synthetic articles
US3321099A (en) * 1963-02-04 1967-05-23 Dow Chemical Co Composition for the lamination of glass by means of epoxy resinous materials
US3328319A (en) * 1963-12-21 1967-06-27 Henkel & Cie Gmbh Process for the hardening of epoxide resins
US3361685A (en) * 1964-12-24 1968-01-02 Agriculture Usa Fluorinated glycidyl ethers and use thereof
US3377406A (en) * 1963-12-16 1968-04-09 Shell Oil Co Process of esterification of polyepoxides with ethylenically unsaturated monocarboxylic acids in the presence of onium salts of inorganic acids
US3382030A (en) * 1963-11-08 1968-05-07 Agriculture Usa Modification of cellulose with butadiene diepoxide using a dioxane-water solvent system
US3402988A (en) * 1965-04-02 1968-09-24 Agriculture Usa Chemical deactivation of catalyst at both faces of a cellulosic fabric impregnated with a resin-catalyst system to improve abrasion resistance of fabric after curing
US3408184A (en) * 1965-01-18 1968-10-29 Xerox Corp Electrophotographic materials and methods employing photoconductive resinous charge transfers complexes
US3408182A (en) * 1965-01-18 1968-10-29 Xerox Corp Electrophotographic materials and methods employing photoconductive resinous charge transfer complexes
US3506392A (en) * 1964-12-30 1970-04-14 Shell Oil Co Modification of cellulose with vaporous epihalohydrin using two distinct steps of reaction catalysis
US3627720A (en) * 1967-02-13 1971-12-14 Ciba Ltd Epoxide-containing compositions
US4049851A (en) * 1975-03-21 1977-09-20 Basf Aktiengesellschaft Manufacture of bonded textile sheet materials
US4240971A (en) * 1969-07-18 1980-12-23 Hercules Incorporated Epoxy-sulfonylazide compounds
EP1138819A3 (en) * 2000-03-31 2003-03-26 Kao Corporation Fiber product treating agents
EP2910675A4 (en) * 2012-10-16 2016-06-22 Nippon Sanmo Deying MODIFIED FIBER AND METHOD FOR THE PRODUCTION THEREOF

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US2829072A (en) * 1954-05-19 1958-04-01 Bates Mfg Co Process for the treatment of textile materials with epoxy resins and for curing the same
BE541693A (en)) * 1954-10-04 1900-01-01
GB796815A (en) * 1955-02-22 1958-06-18 Courtaulds Inc Improvements in and relating to the production of an aminoplast precondensate for the treatment of cellulosic textile materials
DE1155666B (de) * 1957-11-02 1963-10-10 Schickedanz Ver Papierwerk Verfahren zur Herstellung von saugfaehigen und wasserbestaendigen Flaechengebilden aus Cellulosefasern

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US2589245A (en) * 1945-12-03 1952-03-18 Devoe & Raynolds Co Amide-epoxide compositions, etc.
US2494295A (en) * 1946-09-13 1950-01-10 Devoe & Raynolds Co Compositions of resinous epoxides and aromatic sulfonamide-aldehyde condensates
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Cited By (50)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3073662A (en) * 1963-01-15 Process for the production of fast dye-
US2829071A (en) * 1954-04-26 1958-04-01 Shell Dev Treatment of wool containing textiles
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
US2841595A (en) * 1955-01-31 1958-07-01 Shell Dev Process for manufacture of glycidyl ethers of polyhydric phenols
US2848435A (en) * 1955-03-28 1958-08-19 Shell Dev Process for the manufacture of epoxy resins
US2913356A (en) * 1955-06-28 1959-11-17 Shell Dev Preparation of paper having improved wet strength
US2826514A (en) * 1955-11-17 1958-03-11 Shell Dev Treatment of textile materials and composition therefor
US3000690A (en) * 1956-02-06 1961-09-19 Rohm & Haas New polymers of unsaturated glycidyl ethers and methods for producing them
US2886472A (en) * 1956-04-27 1959-05-12 Shell Dev Treatment of textile materials
US2794754A (en) * 1956-04-30 1957-06-04 Shell Dev Treatment of textile materials
US2928803A (en) * 1956-10-05 1960-03-15 Devoe & Raynolds Co Inc Curing of polyepoxides
US2928807A (en) * 1956-10-05 1960-03-15 Devoe & Raynolds Co Inc Curing of polyepoxides
US2928794A (en) * 1956-12-05 1960-03-15 Devoe & Raynolds Co Inc Curing of polyepoxides
US2928808A (en) * 1956-12-10 1960-03-15 Devoe & Raynolds Co Inc Curing of polyepoxides
US2869970A (en) * 1957-04-11 1959-01-20 Edward M Filachione Tanning with epoxy resins
US3024080A (en) * 1957-10-14 1962-03-06 Rohm & Haas 2, 6-dioxaspiro (3, 3)heptane treated cellulose fabric and the production thereof
US2928810A (en) * 1957-11-15 1960-03-15 Devoe & Raynolds Co Aliphatic alcohol-epoxide resin compositions
US2928811A (en) * 1957-11-18 1960-03-15 Devoe & Raynolds Co Epoxide resin-amide compositions
US3036041A (en) * 1957-12-23 1962-05-22 Richardson Co Reaction products of epoxylated compositions and process
US3073799A (en) * 1958-01-20 1963-01-15 Gen Electric Resin compositions and their preparation
US3196117A (en) * 1958-06-19 1965-07-20 Archer Daniels Midland Co Intermolecular alkyd-epoxy complexes
US3019076A (en) * 1958-07-22 1962-01-30 Jr Clay E Pardo Treatment of textiles with polyepoxides and polyamides
US3043813A (en) * 1958-10-03 1962-07-10 Union Carbide Corp Polymer of alkenyl epoxycyclopentyl ethers
US3128147A (en) * 1959-09-30 1964-04-07 Courtaulds Ltd Process for treating polynosic fibers and products obtained thereby
US3026216A (en) * 1959-10-05 1962-03-20 Union Carbide Corp Treatment of textile fabrics with methylglycidyl ethers
US3084073A (en) * 1959-12-10 1963-04-02 Rohm & Haas Copolymers of alkyl acrylate, methoxymethyl vinyl sulfide, comonomer containing functional groups, and coating compositions thereof
US3097050A (en) * 1959-12-28 1963-07-09 Rohm & Haas Process of creaseproofing cellulose fabrics with 2, 6-dioxaspiro (3, 3) heaptane and ormaldehyde and fabrics produced thereby
US3150190A (en) * 1960-02-18 1964-09-22 Quaker Chem Corp Acetal condensation products and their preparation
US3206328A (en) * 1960-03-01 1965-09-14 American Cyanamid Co Process for imparting anti-static properties to hydrophobic textile materials and product thereof
US3131083A (en) * 1960-03-25 1964-04-28 Standard Packaging Corp Method of impregnating card stock
US3228920A (en) * 1960-05-12 1966-01-11 Metal Recovery Systems Chelating resins and method of preparation
US3069311A (en) * 1962-03-28 1962-12-18 Hercules Powder Co Ltd Paper manufacture
US3321099A (en) * 1963-02-04 1967-05-23 Dow Chemical Co Composition for the lamination of glass by means of epoxy resinous materials
US3382030A (en) * 1963-11-08 1968-05-07 Agriculture Usa Modification of cellulose with butadiene diepoxide using a dioxane-water solvent system
US3377406A (en) * 1963-12-16 1968-04-09 Shell Oil Co Process of esterification of polyepoxides with ethylenically unsaturated monocarboxylic acids in the presence of onium salts of inorganic acids
US3328319A (en) * 1963-12-21 1967-06-27 Henkel & Cie Gmbh Process for the hardening of epoxide resins
US3293073A (en) * 1964-02-12 1966-12-20 Union Carbide Corp Process for imparting wash and wear properties to cellulose-containing textile fabric and resulting product
US3293071A (en) * 1964-02-14 1966-12-20 Union Carbide Corp Process for treating cellulosic textile material
US3313796A (en) * 1964-02-24 1967-04-11 Monsanto Co Process for improving the antistatic properties of synthetic articles
US3361685A (en) * 1964-12-24 1968-01-02 Agriculture Usa Fluorinated glycidyl ethers and use thereof
US3506392A (en) * 1964-12-30 1970-04-14 Shell Oil Co Modification of cellulose with vaporous epihalohydrin using two distinct steps of reaction catalysis
US3408184A (en) * 1965-01-18 1968-10-29 Xerox Corp Electrophotographic materials and methods employing photoconductive resinous charge transfers complexes
US3408182A (en) * 1965-01-18 1968-10-29 Xerox Corp Electrophotographic materials and methods employing photoconductive resinous charge transfer complexes
US3402988A (en) * 1965-04-02 1968-09-24 Agriculture Usa Chemical deactivation of catalyst at both faces of a cellulosic fabric impregnated with a resin-catalyst system to improve abrasion resistance of fabric after curing
US3627720A (en) * 1967-02-13 1971-12-14 Ciba Ltd Epoxide-containing compositions
US4240971A (en) * 1969-07-18 1980-12-23 Hercules Incorporated Epoxy-sulfonylazide compounds
US4049851A (en) * 1975-03-21 1977-09-20 Basf Aktiengesellschaft Manufacture of bonded textile sheet materials
EP1138819A3 (en) * 2000-03-31 2003-03-26 Kao Corporation Fiber product treating agents
US6660044B2 (en) 2000-03-31 2003-12-09 Kao Corporation Fiber product-treating agents
EP2910675A4 (en) * 2012-10-16 2016-06-22 Nippon Sanmo Deying MODIFIED FIBER AND METHOD FOR THE PRODUCTION THEREOF

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BE515900A (en))
GB732573A (en) 1955-06-29
FR1071905A (fr) 1954-09-07
NL174182B (nl)
DE1024049B (de) 1958-02-13

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