US3703351A - Two step modification of textile materials - Google Patents

Two step modification of textile materials Download PDF

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US3703351A
US3703351A US14712A US3703351DA US3703351A US 3703351 A US3703351 A US 3703351A US 14712 A US14712 A US 14712A US 3703351D A US3703351D A US 3703351DA US 3703351 A US3703351 A US 3703351A
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textile
reaction
fabric
dry
alkaline
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Michael V Lock
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Deering Milliken Research Corp
Milliken Research Corp
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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
    • D06M15/39—Aldehyde resins; Ketone resins; Polyacetals
    • D06M15/423—Amino-aldehyde resins
    • 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
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/402—Amides imides, sulfamic acids
    • 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
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/402—Amides imides, sulfamic acids
    • D06M13/41—Amides derived from unsaturated carboxylic acids, e.g. acrylamide
    • 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
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/402—Amides imides, sulfamic acids
    • D06M13/41—Amides derived from unsaturated carboxylic acids, e.g. acrylamide
    • D06M13/412—N-methylolacrylamides
    • 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
    • Y10S8/21—Nylon

Definitions

  • a reducing agent may be added to the treating bath to inhibit yellowing of the textile material under curing conditions.
  • An aminoplast resin may be included in the treating bath.
  • Active hydrogen containing compounds may be appended to the textile through reaction with reactive groups bound to the textile by the initial reaction between the polyfunctional compound and the textile.
  • This invention relates to methods for treating cellulosic materials to improve certain characteristics thereof, particularly the flat drying properties, to the cellulosic materials thus obtained and to certain cellulose ethers.
  • polyfunctional compounds generally must be accompanied by additional compounds to build up the performance in either or both the wet and dry state.
  • the polyfunctional compounds utilized in the processes of this invention may be utilized alone to provide excellent wet and dry resiliency properties in the fabric and, consequently, excellent flat drying properties.
  • the polyfunctional compounds utilized herein are highly eificient in their reactivity with hydroxy groups of cellulose, so that for a given performance requirement, less of the polyfunctional compounds utilized herein is required than would be required for other polyfunctional compounds.
  • Still another object of this invention is to provide such a process wherein the residual strength of the cellulosic material is as high or higher than any previously known process for the modification of cellulosic materials.
  • the reaction product of an acrylamide and an aldehyde preferably contains at least two groups reactive with hydroxy groups of cellulose under textile resin curing conditions, i.e., acid-reactive groups, and at least one group reactive with hydroxy groups of cellulose under alkaline conditions, i.e., base-reactive groups.
  • permanent dry resiliency properties can be imparted to the cellulosic material by conducting the acid-reaction first and under textile resin-curing con ditions wherein the cellulosic material is substantially dry and in a flat state.
  • the reaction product is chemically afiixed tothe cellulose molecule through the cross-links formed, so that subsequent cross-linking operations can be conducted under any desired condition without destroying the dry resiliency properties of the cellulosic material.
  • the base-reactive groups of the reaction product are then reacted with hydroxy groups of cellulose, preferably while the cellulosic material is swollen with a strong alkaline catalyst, whereby excellent wet resiliency properties are obtained.
  • Typical reaction products suitable for use in accordance with this invention include those derived from acrylamides, including alkylene-bis-acrylamides, and saturated or unsaturated aldehydes, preferably simple ones like formaldehyde.
  • Preferred reaction products are believed to have a formula characterized by wherein R is selected from hydrogen, lower alkyl and the residue of a saturated or unsaturated aldehyde; R is selected from hydrogen and lower alkyl, preferably methyl; and R is selected from hydrogen and lower alkyl; and X is selected from oxygen and sulfur.
  • the R O groups of the above compounds react with hydroxy groups of cellulose under textile resin curing conditions to give permanent dry resiliency properties.
  • the -CR CH groups of the above compounds react with hydroxy groups of cellulose, preferably in the swollen state provided by an alkaline catalyst, to give permanent wet resiliency properties.
  • Cell-O-CHR X N-ii-C R CHg Cell-O-CHR wherein Cell is the residue of a cellulose molecule of said material; R is selected from hydrogen, lower alkyl and the residue of a saturated or unsaturated aldehyde; X is selected from oxygen and sulfur; and R is selected from hydrogen and lower alkyl, preferably methyl.
  • the alkaline reaction is believed to provide a crosslinked structure of the formula:
  • Cell-O-CHR (III) Cell-O-OHR wherein Cell is the residue of a cellulose molecule of said material; R is selected from hydrogen, lower alkyl and the residue of a saturated or unsaturated aldehyde, and R is selected from hydrogen and lower alkyl.
  • R R and X are as before, R being hydrogen, lower alkyl or CHR OR wherein R is as before.
  • Typical compounds include that derived from acrylamide and glyoxal (wherein R R and R are hydrogen and X is oxygen) and the N-methylol, di-N-methylol derivatives thereof.
  • reaction products of haloacetamides and aldehydes e.g., those characterized by the formula:
  • R R and R are hydrogen and X is oxygen.
  • U.S. Pats. Nos. 2,837,511 and 2,837,512 disclose various processes for producing cellulose ethers, such as by reacting cellulose with polyfunctional compounds like N- methylolacrylamide in a two-step operation whereby the acid curing groups are first attached to cellulose (US. 2,837,512), after which the resulting cellulose ether is soaked in strong base solution at room temperature (US. 2,837,511) to produce a cross-linked product, which has only wet resilience properties. For example, a cellulosic fiber will acquire resiliency in the state in which the molecules thereof are cross-linked.
  • a fiber For example, if a fiber is cross-linked while in a wet, swollen state, it will acquire wet resiliency only. Such a fiber will have a high spin rating, in that it will be resilient in the wet state, but will have a low tumble rating since no dry resiliency is imparted during wet cross-linking. The reverse is true.
  • a cellulosic fiber which is cross-linked in the dry state will acquire only dry resiliency and will be characterized by a high tumble rating and low spin rating.
  • the only cross-linking disclosed in the above-identified patents occurs in the wet, swollen state, so that only wet resiliency is imparted to the rayon fibers.
  • the monofunctional attachment of N-methylol acrylamide to cellulose which occurs during the initial acidside reaction disclosed in the above-identified patents is insufficient to impart satisfactory dry resiliency to the fibers treated therein, and consequently, no product disclosed in the above-identified patents would have satisfactory tumble ratings.
  • the cellulose ethers disclosed in the above-identified patents are highly susceptible to chlorine damage as a result of attack of hydrochlorous acid on the free amido hydrogen atom of both the monofunctionally attached cellulose ether and in the final cross-linked product.
  • the degree of improvement obtained during the alkaline reaction with the polyfunctional compounds of this invention far exceeds that obtained with polyfunctional compounds similarly used in the art.
  • the response to the alkaline reaction using previous polyfunctional compounds rarely exceeds 1.0 rating unit and more often is about 0.5 rating unit.
  • the desired reaction under alkaline conditions will occur at room temperature conditions after suitable ageing or the fabric can be heated to increase the rate of the desired reaction.
  • the rate of desired reaction can be increased 'by heating the wet, swollen cellulosic material to any desired temperature, preferably from room temperature up to about 200 C. where strong alkaline'catalysts are used and to temperatures of at least about 80 C. where milder alkaline catalysts, such as sodium bicarbonate and sodium carbonate, are utilized.
  • the wet, swollen material can be heated on conventional equipment such as over hot cans, in tenter frames, 'with hot calendar rolls, conventional heating ovens, vat dryers, and the like.
  • the fabric can be passed back and forth through a vat dryer, the dwell time being from about 1 to about minutes, to provide substantial reaction whereby the fabric is set in the fiat configuration in which it is passed through the vat dryer.
  • the same effect can be noticed by passing over a plurality of cans heated to high temperatures, for example, up to about 130 C., or by passing on a tenter frame through a heated chamber.
  • the fabric impregnated with the alkaline catalyst is exposed to steam during the cure, in that steam greatly enhances the desired reaction.
  • the amount of polyfunctional compound which can be employed is not critical and the exact amount to be employed depends in part on the properties desired in the final product and the efficiency of the selected compound. For example, amounts in the range of from about 1 to about 40%, preferably about 5 to about 15% calculated on the weight of the dry textile material, or more or less, can be applied to the textile material as desired.
  • At very high pick-ups of the polyfunctional compound no more improved results are obtained but fabric strength may be diminished. It is a distinct advantage of the present process, however, that far less strength loss is realized during the process of this invention than accompanies processes wherein a fabric is treated with both an acidreacting textile resin and a base-reacting reagent.
  • the polyfunctional compound may be applied to the cellulosic material as a single compound having at least two acid-reactive and at least one base-reactive group in the molecule as shown in Formula I, although a mixture of the compounds from which the polyfunctional compounds are prepared may be utilized.
  • a solution containing an acrylamide compound, at least 1.5 moles per mole thereof of formaldehyde and, if desired, an acid-acting catalyst may be prepared and padded onto the cellulosic material being treated.
  • the acrylamide compound and excess formaldehyde, or other aldehyde compound may be reacted in an aqueous solution of a mixture of these compounds, especially if heated, in which case the resulting product would have two acid-reactive groups and one base-reactive group in the molecule as set forth above, provided a sufficient amount of the aldehyde is utilized for reaction with substantially all amido-hydrogen atoms of the acrylamide.
  • the textile resin catalysts employed during the heating step under textile resin conditions are a well-known class of compounds and include the acid-acting compounds, that is, those compounds which are acidic in character under the curing conditions.
  • the most common are the metal salts, for example, magnesium chloride, zinc nitrate and zinc fluoroborate and the amino salts, for example, monoethanolamine hydrochloride and 2-amino-2-methyl propanol nitrate.
  • the amounts of catalyst to be employed are the same as those employed when using the usual textile resins, for example, up to about 20% by weight of the acid reacting compound employed, with the preferred range being from about 0.5 to about 10%.
  • any acid-acting catalyst may be utilized, it is generally preferred to use a strong acid catalyst, such as zinc nitrate and the like, in that improved properties, such as improved wet'and dry resiliency properties are obtained with the stronger acid catalyst.
  • a strong acid catalyst such as zinc nitrate and the like
  • improved properties such as improved wet'and dry resiliency properties are obtained with the stronger acid catalyst.
  • milder acid catalysts it is recommended that higher temperatures and longer cure times be utilized.
  • compounds like zinc nitrate which produce relatively low pH values in the fabric during curing, are considered strongly acidic, whereas compounds like magnesium chloride are considered mildly acidic.
  • additives commonly employed when using the usual textile resins can be employed in the process of this invention.
  • a small amount of a 'surface active agent can be added to insure uniform and satisfactory wetting out of the fabric, if an aqueous solution is employed.
  • Softeners for example the dispersible polyethylenes, can be added to improve the handle of textile materials being treated.
  • textile resins may be utilized in combination with the polyfunctional compounds disclosed herein to improve certain properties, such as the dry resiliency property, if desired. In general, however, no such improvement is necessary and, if anything, the addition of a textile resin tends to minimize the effect obtained by the use of the polyfunctional compound by itself.
  • textile resin as used herein is in conformity with the generally accepted usage in the textile industry, i.e., it defines a thermosetting reagent which is applied to a textile fabric and reacted therewith when the dry fabric is heated, usually in the presence of an acidic catalyst, at a temperature usually between about 140 and about 200 C. These conditions are normally referred to herein as textile resin curing conditions.
  • urea-formaldehydes and the melamine-formaldehydes for example dimethylol urea and tetra and penta-methylolmelamines; the acrolein-urea-formaldehyde resins; the cyclic ethylene urea-formaldehyde resins, e.g., dimethylol cyclic ethylene urea and dimethylol dihydroxy cyclic ethylene urea, trimethylol-acetylene diurea and tetramethylolacetylene diurea; the triazones, e.g., dimethylol-N-ethyltriazone, dimethylol-N-hydroxy ethyl-triazone and the like.
  • the strong aqueous bases preferably employed as the catalyst in the second curing operation of the process of this invention are those having a pH of at least about as a 1% aqueous solution.
  • the bases most commonly employed are the alkali-metal hydroxides, although other compounds such as sodium silicate, sodium carbonate and potassium carbonate which produce slightly lower pHs in the fabric during the wet curing stage can also be employed. If these latter type compounds are utilized, it is preferred that the temperature in the base curing step be increased preferably above about 80 C.
  • alkali-metal hydroxides are preferred, additional base-acting catalysts may be utilized, e.g., potassium bicarbonate, potassium carbonate, alkali-metal phosphates such as sodium and potassium phosphate, barium carbonate, quaternary ammonium hydroxides and carbonates, e.g., lauryl trimethyl ammonium hydroxide and carbonate and the like.
  • potassium bicarbonate potassium carbonate
  • alkali-metal phosphates such as sodium and potassium phosphate
  • barium carbonate e.g., barium carbonate
  • quaternary ammonium hydroxides and carbonates e.g., lauryl trimethyl ammonium hydroxide and carbonate and the like.
  • bases are usually employed as about 0.2% to about 16% solutions, preferably about 2 to about 16%.
  • concentration while not critical, will affect the results obtained.
  • concentration which gives the optimum result will depend in part on the percent pick-up of the base by the textile material, the temperature at which the reaction is conducted and the amount of base consumed in the reaction. If a highly acidic group is released during the reaction, the amount of base applied to the textile material should be at least the amount that will be consumed by that group. Generally, a 3% to 10% aqueous solution of base is preferred when the pick-up is between about 30% to 130% calculated on the weight of the dry cellulosic material.
  • the cellulosic material uniformly impregnated with the polyfunctional organic compound is heated under textile resin curing conditions in the pres ence of a textile resin catalyst, for example an acid-acting catalyst.
  • a textile resin catalyst for example an acid-acting catalyst.
  • the polyfunctional compound containing at least two acid reactive and at least one base reactive group can be that which is initially applied to the textile material or can be the product of an in situ reaction of the acid-reactive group contributing compound and the base-reactive group contributing compound.
  • this steps employs conditions identical to that of a conventional resin treatment.
  • the selected reagents can be applied to the cellulosic material by padding, spraying or applicator roll and then passed through squeeze rolls, if neces sary, to achieve the desired pick-up of the reagents.
  • the cellulosic material is dried and then heated to the appropriate temperature, for example about to about 200 C., preferably about to about C. to produce the desired intermediate cross-linked cellulosic ether product.
  • these steps of drying and curing are conducted while the fabric is free from extraneous wrinkles, usually in a smooth open width condition.
  • Conventional curing equipment is suitable for this operation.
  • the reagents can be applied with the usual equipment and then passed through squeeze rolls and dried, e.g., at room temperature or while the fabric passes through a hot air oven or over heated cans. In production, it is preferred to conduct the heating operations in a tenter frame to maintain the desired dimensions.
  • the thus treated cellulosic material is then ordinarily given a thorough wash to remove the catalyst and any unreacted reagents. If suflicient reagents are employed in this step, the cellulosic material will be found to possess a high degree of dry resiliency and somewhat improved wet resiliency at this stage.
  • the textile material is then contacted with the desired base-acting catalyst.
  • the reaction can be reversed.
  • the base reaction can be conducted initially followed by the acid reaction.
  • the initial cellulose ether would be characterized by high Wet resiliency properties which would be permanent under the conditions by which the acid reactive groups are reacted with hydroxy groups of cellulose provided at least two base-reactive groups are present in the polyfunctional compound.
  • the step of contacting the cellulosic material with the desired base acting catalyst employs conditions generally employed in the textile trade and the necessary techniques will be apparent to those skilled in the art.
  • impregnating the cellulosic material with the selected base acting catalyst can be accomplished in a manner similar to those employed in the previous step.
  • the cellulosic material can be moistened by dipping in an aqueous solution of the selected base and squeezed through rollers to achieve the desired pick-up of the base.
  • the textile material is ordinarily maintained with a pick-up of from about 30% to about 130% calculated on the weight of the dry textile materia[l).7'I'he preferred pick-up is from about 50% to about 10 o.
  • Textile materials which can be treated according to the processes of this invention are those in which the anhydroglucose units are chemically substantially unmodified.
  • cellulosic textile material when used herein means any textile material comprising fibers within the above definition, e.g., cotton, paper, linen, jute, flax, regenerated cellulose fibers, including viscose rayon, in the form of staple, yarn and fabrics.
  • This invention is directed primarily and preferably to cellulosic textile fabrics, either knitted or woven, preferably woven.
  • the advantages of this invention can be achieved by treating the cellulosic fibers, yarns, or threads employed to produce these fabrics.
  • the thus treated material when woven or knitted into fabric will produce a fabric having better wet and dry resiliency than identical fabric woven from identical untreated yarn or thread.
  • the properties of the staple yarn and thread are modified in a desirable fashion. For example, the staple is less prone to compression into hard masses during wet or dry processing.
  • cellulosic materials containing both cellulosic and non-cellulosic fibers can be improved by this process.
  • polyester such as poly(ethylene terephthalate) polyamide such as poly(hexamethylene adipamide)
  • acrylic fibers such as polyacrylonitrile and copolymers containing at least about 85% combined acrylonitrile filaments or fibers with cotton or rayon can be improved by this process.
  • the improved characteristics of the materials treated according to the processes of this invention will be more readily apparent when the cellulosic content of the fabric is substantial, e.g., about 40% or more by weight.
  • the invention is primarily directed to fabrics, preferably consisting essentially of cellulosic materials, especially cotton. Bleached and usually also commercially mercerized or printed fabric, e.g., printcloth, broadcloth, and oxford cloth, is usually employed as the starting fabric.
  • the cellulosic material preferably contains at least about 1.8 unsubstituted hydroxy groups and at least 0.05 hydroxy groups per anhydroglucose unit substituted through two ether linkages by a radical having a terminal grouping reactive towards hydroxy groups of cellulose;
  • the substituent is base-reactive.
  • Such degree of substitution is preferred for the desired cross-linking reaction to take place to a satisfactory extent.
  • an average of at least 0.05, more preferably 0.20.5 hydroxy groups per anhydroglucose unit is substituted through an ether linkage to one of the R groups set forth above.
  • the cellulosic material can have a minor proportion of hydroxy groups substituted with ether or ester groups, e.g., lowerhydrocarbon esters including the acetate, propionate,
  • reducing agents such as alkali-metal borohydride, such as sodium and potassium borohydride; alkanolamine sulfites, such as monoethanolamine sulfite, monoisopropanolamine sulfite and others containing up to about 8 carbon atoms in the alkyl chain and the like can be applied to the cellulosic material being treated to inhibit any yellowing which may tend to occur under setting conditions in the garment state.
  • alkali-metal borohydride such as sodium and potassium borohydride
  • alkanolamine sulfites such as monoethanolamine sulfite, monoisopropanolamine sulfite and others containing up to about 8 carbon atoms in the alkyl chain and the like
  • sodium borohydride is applied along with sodium bicarbonate or sodium carbonate, the time of curing is reduced, e.g., to 30-60 seconds with no yellowing of the fabric when steam is used, whereas without steam as much as 5 minutes would be required to
  • cellulose ethers formed during the acid-side cure above may be reacted with active hydrogen compounds in addition to cellulose. Also, in most instances, a sufiicient number of terminal ethylenically unsaturated groups remain after the alkaline reaction to enable further reaction to take place between the cellulose ethers and other active hydrogen compounds to form cellulose ethers of the formula:
  • Cell-O-CHR' wherein Cell is the residue of a cellulose molecule of the cellulosic material, R' is selected from hydrogen, lower alkyl and the residue of a saturated or unsaturated aldehyde, R is selected from hydrogen and lower alkyl, preferably methyl, X is selected from oxygen and sulfur and Z is the residue of an active hydrogen compound wherein the active hydrogen atom is linked to an atom selected from the group consisting of sulfur, nitrogen, phosphorus and oxygen.
  • cellulose ethers produced in accordance with this invention as with active hydrogen compounds like hydrogen sulfide, mercaptans, ammonia, amines, phosphites and alcohols.
  • active hydrogen compounds like hydrogen sulfide, mercaptans, ammonia, amines, phosphites and alcohols.
  • Representative compounds include hydrogen sulfide, benzyl mercaptan, octadecyl mercaptan and the like; ammonia, piperidine, octyl amine, morpholine, ethylene diamine, octadecylamines, p-toluidine and the like; diethyl phosphite, dibutyl phosphite, diphenyl phosphite and the like; aliphatic alcohols, cellulose esters and ethers as set forth above, and the like.
  • EXAMPLE II The aqueous reaction product prepared according to the procedure of Example I is made up to aqueous solu- 12 hydroxide solution. To this solution is added 710 gms. of acrylamide (10 moles) and 3 gms. of methylhydroquinone inhibitor. With the pH still held at 10.0, the solution is heated at 60 C. for one hour, cooled and tions of the following compositions: 30% of the solu- 5 than neutralized to 3 PH of 75 by the addition 3 non of Example 1% or 15% of mm nitrate hexahy' N-hydrochloric acid. Sufficient water is then added to draw 6% of Moropol 700 Polyfithylene Softener and increase the total weight to 2660 gms.
  • EXAMPLE III to aqueous solutions of the following composition: 10%
  • the procedure of Example H is followed, employing (solid s) of one of the above-mentioned reaction products, a resin mixture containing the aqueous reaction product 40 1% Zlnc filtrate hexahydfate catalyst, 6% MOFOPO1 700 of Example I (13.5, 24 or 27%); a modified melamine polyethylene softener and 13% Surfonic N-95 surfactant.
  • EXAMPLE IV 1620 grns. of 37% formaldehyde (20 moles) is adjusted to a pH of 10.0 by the addition of 5 N-sodium C. for 1.5 minutes. After washing, the fabrics possess the physical properties shown in Table III.
  • Example IIX The procedure of Example VIII is repeated except that the zinc nitrate catalyst concentration is varied while the concentration of the reaction product of Example IV is held constant at 10% (solids). The properties of the fabrics thereby obtained are shown in Table V.
  • aqueous reaction product prepared according to the procedure of Example IV is made up to an aqueous solution of the following composition: 6% (solids) of the above-mentioned reaction product, 0.6% zinc nitrate hexahydrate catalyst, 6% Moropol 700 polyethylene soft- TABLE V Dry fill Dry fill Sodium tensile tear Spin Tumble 8 a ys 00112811 1'8 011 y 0X 8 S reng S reng a ry 8 ry Ctlt tti hdrid t th t thfltd fltd (percent Zn(NO1) 261110) treatment (1b.) (gm rating rating Control 71.
  • Example VIII EXAMPLE X ener and /s% Surfomc N-95 surfactant.
  • the resultant The procedure of Example VIII is repeated, employing a solution containing the aqueous reaction product of Example IV (10% solids), 1% of zinc nitrate hexahydrate catalyst, a polyethylene softener (6% Moropol 700 or 10% Syn-Soft LS) and /3 of Surfonic N-95 Surfactant.
  • the fabrics possessed the physical properties shown in Table VI.
  • Thep'hysical properties of a sample (designated A in Table VIII) of the fabric thereby obtained are measured.
  • Other fabric samples are padded with 2% aqueous sodium hydroxide, placed in a steam atmosphere in a conditioning oven at 100 C. for 5 minutes and then immediately washed and dried.
  • the physical properties of a sample (designated B in Table VIII) of this fabric are also measured.
  • Example VIII Dry fill Dry fill tensile tear Spin Tumble strength strength fiat dry flat dry Sample (lb (gm.) rating rating
  • EXAMPLE XIII The procedure of Example VIII is repeated, using the solution of Example XI, but in this case the after-treat- 15 ment with 2% aqueous sodium hydroxide is conducted in a steam autoclave (120 C. at 20 lbs. pressure) for 5 minutes, and the fabric is then immediately washed and dried. Table IX shows the physical properties of the thus treated fabrics.
  • EXAMPLE XVIII The remainder of the fabric is padded to a pick-up of about with 2% aqueous sodium hydroxide containing 1% of a surfactant (Mercerol GV), rolled up, held at room temperature for 16 hours, washed in 0.5% acetic acid, thoroughly washed in water and detergent, and dried.
  • a surfactant Mercerol GV
  • Table X The physical properties of the resultant fabric are shown in Table X, together with the same properties after typical home laundering procedures.
  • Example XVI The procedure of Example XVI is repeated, but in this case the reaction with 2% aqueous sodium hydroxide is accomplished by passing the wet fabric through an atmosphere of steam for nine minutes at C. in a Vat Ager. The process is also repeated using 4% aqueous sodium hydroxide or 2.5% aqueous sodium carbonate in place of the 2% aqueous sodium hydroxide. The addition of 0.2% sodium borohydride to the alkali solution prevents any yellowing of the fabric during the steaming process. The properties of the thus treated fabrics are shown in Table XIII.
  • Example XXI The procedure of Example VIII is repeated, except that the aqueous reaction product of Example XX is employed in place of the reaction product of Example IV. Essentially similar results but with lower Flat Dry Ratings, are obtained.
  • EXAMPLE XXII The reaction product of glyoxal with two molar equivalents of acrylamide is used in place of the reaction product of Example IV in the procedure of Example VIII.
  • This reaction product is prepared in the following manner: Two hundred and eighty-five gms. of 40% glyoxal (2 moles) and 95 gms. water are adjusted to a pH of 8.0 with 1. O N-sodium hydroxide solution. Two hundred and eighty-four gms. of acrylamide (4 moles) and 3 gms. of methylhydroquinone inhibitor are added and the mixture is heated at 50 C. for 1.5 hours and cooled. Results essentially similar to those of Example XXI are obtained when this reaction product is employed in the procedure of Example VIII.
  • Example XXIH The procedure of Example VIII is repeated except that the reaction product of 1 mole of acrolein and 3 moles of acrylamide condensed at pH 2 by heating at 60 C. for 30 minutes is employed. The fabric is padded with a 50% solution (adjusted to pH 9) of the reaction product containing 3 moles of formaldehyde. Results essentially similar to those of Example XXI are obtained.
  • a process for improving the properties of a fabric which comprises:
  • step (c) thereafter impregnating said fabric with an acid catalyst if a basic catalyst was used in step (a) or a basic catalyst if an acid catalyst was used in step (a);

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  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3901014A (en) * 1972-07-19 1975-08-26 Kanebo Ltd Method for crimping cellulosic fibers and crimped cellulosic fibers obtained thereby
US3926555A (en) * 1973-03-16 1975-12-16 Us Agriculture Modification of cotton textiles and cotton/polyester textile blends by photo-initiated polymerization of vinylic monomers
US4052158A (en) * 1973-11-12 1977-10-04 Stauffer Chemical Company Textile finishing process
US4717600A (en) * 1984-11-23 1988-01-05 Montefibre S.P.A. Process for improving the touch and draping characteristics of textile products based on polyester

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3901014A (en) * 1972-07-19 1975-08-26 Kanebo Ltd Method for crimping cellulosic fibers and crimped cellulosic fibers obtained thereby
US3926555A (en) * 1973-03-16 1975-12-16 Us Agriculture Modification of cotton textiles and cotton/polyester textile blends by photo-initiated polymerization of vinylic monomers
US4052158A (en) * 1973-11-12 1977-10-04 Stauffer Chemical Company Textile finishing process
US4717600A (en) * 1984-11-23 1988-01-05 Montefibre S.P.A. Process for improving the touch and draping characteristics of textile products based on polyester

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