US3476581A - Treatment of textiles with cross-linkable acrylic polymers and the resulting products - Google Patents

Treatment of textiles with cross-linkable acrylic polymers and the resulting products Download PDF

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Publication number
US3476581A
US3476581A US497519A US3476581DA US3476581A US 3476581 A US3476581 A US 3476581A US 497519 A US497519 A US 497519A US 3476581D A US3476581D A US 3476581DA US 3476581 A US3476581 A US 3476581A
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Prior art keywords
hose
cross
emulsion
treatment
garments
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US497519A
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Edward W Weitzel
Charles H Hamby
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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
    • D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/285—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acid amides or imides
    • D06M15/29—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acid amides or imides containing a N-methylol group or an etherified N-methylol group; containing a N-aminomethylene group; containing a N-sulfidomethylene group
    • 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
    • D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/263—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof
    • 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
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31—Surface property or characteristic of web, sheet or block
    • 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
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
    • Y10T442/241—Coating or impregnation improves snag or pull resistance of the fabric

Definitions

  • This invention relates to a process and resulting article wherein a textile material is treated with a polymeric emulsion to increase the materials resistance to pulling, snagging and picking.
  • On object of the present invention is to provide textile articles including sheer stockings which have exceptional resistance to picking, running or snagging, while demonstrating excellent hand and stretch characteristics.
  • a process is pro vided for treating a textile article with an aqueous liquid wherein the liquid contains a polymeric substance comprised of at least some acrylic monomers, some of which are esters.
  • the polymers and copolymers that are useful in this invention are those acrylic emulsion polymers that crosslinkor cure to form a relatively soft film. These polymers should combine softness, resilience and low temperature flexibility with improved dry cleaning fastness and excellent wash fastness. These polymers should be cross-- 3,476,581 Patented Nov. 4, 1969 linkable which means that should either be self crosslinking or possible of reacting or curing in situ with a nitrogeneous or other type of external cross-linking agent, under the curing conditions of this invention set forth hereinafter. The compound or compounds having groups that are capable of cross-linking may be reacted in situ with the acrylic monomer during the curing step of this procedure if desired, to form a thermosetting type resin.
  • the process of the present invention may be applied to knitted or woven fabrics or articles and is applicable to wool or nylon or mixtures of these materials, and also to fabrics or articles containing wool and/or nylon in admixture with other fibers such as the synthetic protien fibers, e'.g., material known under the name Ardil and the ethylene glycol terephthalic polyesters, e.g., material known under the name Terylene, cotton, rayon, casein fiber, cellulose acetate, e.g., the viscose rayon material known under the name Fibro.
  • synthetic protien fibers e'.g., material known under the name Ardil and the ethylene glycol terephthalic polyesters, e.g., material known under the name Terylene, cotton, rayon, casein fiber, cellulose acetate, e.g., the viscose rayon material known under the name Fibro.
  • articles which may be treated according to the present invention are underwear, or outerwear garments, hose, half-hose, quarter-hose, three-quarter hose, socks and stockings, felts, hats, ties, furnishing fabrics, upholstery for motor cars, gloves, scarves, curtains, etc.
  • the process of the invention may be applied to a dyed or undyed material.
  • the dyeing may be effected during the process of the present invention or may be effected subsequent to this treatment. It is, however, preferable that the textile materials treated in accordance with this invention should be free of other finishes, i.e. lanolin or the like.
  • the fabrics or articles treated in accordance with this invention shown an increased resistance to picking, snagging or pulling.
  • the term picking as used herein refers to the tendency of sheer fabrics to have unsightly broken threads and holes, this characteristic particularly being present in knitted stockings and the like.
  • the measurement of this physical characteristic of fabrics particularly stockings can be carried out on the Hanes Pick Tester, U.S. Patent 3,044,293.
  • This tester comprises a small cylindrical tumbling device equipped with baffies and with a number of straight pins protruding from the cylinder Wall.
  • the stockings are first board inspected and all defects marked and then put into the pick tester and tumbled for three minutes at approximately 18.8 r.p.m.
  • the straight pins hold the hose as well as" the bafiies in the tumbler thus giving hose a tumbling action.
  • After three minutes in the tester the samples are removed and inspected for defects. Defects are classified as'to their location in the hose (boot or welt). The additional defect totals are recorded.
  • the process of this invention is particularly beneficial in treating garments or fabrics produced from textured textile yarn.
  • One of the textured yarns that is particularly difficult to work with and has been proven to give a relatively high numberof picks, pulls and snags in woven or sheer knitted garments is AGILON yarn or any equivalent edgecrimped yarn.
  • AGILON stockings particularly those knitted from multifilament yarn, i.e., 15 denier, 3 filament willdemonstrate between 10 and 20 picks per hose when tested on the Hanes pick tester described above. After treatment according to the process of this invention, the AGILON stockings will generally when tested on a Hanes pick tester demonstrate from one to five picks per hose, under the same conditions.
  • Garments made from yarn produced from other texi 3 turing methods such as the Pinlon process, covered in part by Patents 2,914,810, 3,153,272 and 3,174,206 will show marked improvement when finished in accordance with the process of this invention.
  • Yarns made by other texturing processes such as Spunize or by other gear crimping, stulfer box or false twist crimping methods can be treated beneficially in ac cordance with this invention and will improve the pick, pull and snag resistance of the garments that are so treated.
  • the polymers that are most useful in this invention are those known to the art as the acrylics, including particularly the acrylates. These polymers may be homopolymers or copolymers so long as the acrylate chain has both ester groups and groups that are capable of cross-linking with the polymeric chain under properly catalyzed conditions. It is, however, preferred that copolymers be utilized for the most part.
  • the polymers utilized in this invention will have molecular weights ranging from about a few hundred, i.e. three hundred to about three million and be comprised from an acrylic monomer having ester groups and a side chain group that is comprised of compounds selected from the group having epoxide, carboxyl and/ or methylol groups.
  • the acrylates and particularly the alkyl acrylate monomers such as methylacrylate, eahylacrylate, propylacrylate, butylacrylate, pentylacrylate and the like up to and including 12 carbon atoms alkyl acrylates.
  • poly-n-butylacrylate having a molecular Weight in the range of one thousand to one million is the preferred species.
  • any of the above acrylic monomers may be reacted with any copolymerizable compounds containing epoxide groups, carboxyl groups or methylol groups.
  • Compounds having functional groups that can be cross-linked are preferably n-methylolacrylamide, glycidyl acrylate, acrylic acid and methacrylic acid.
  • These co-monomers that can react in the copolymerization process or in situ to form a side chain group having an epoxy, carboxy and/or methylol group are usually present in an amount ranging from 0.5 percent to percent by weight of the polymeric material formed.
  • acrylic anhydride glycol esters of acrylic or methacrylic acid and acrylamide may be used.
  • the backgone of the polymeric chain may be comprised of any of the acrylic monomers set out in the book entitled Reaction Of The Acrylic Esters, reprinted from Chapter VI Monomeric Acrylic Esters by E. H. Riddle, published by the Reinhold Publishing Corporation, 430 Park Avenue, New York (Sp-182 copyright 1954 by the Reinhold Publishing Corporation).
  • the polymerization or copolymerization of these acrylic monomers may be carried out with either a persulfate or peroxide catalyst or with a redox catalyst system in accordance with the recipes and formulations set forth in the publication entitled Emulsion Polymerization Of Monomeric Acrylic Esters, published by Rohm and Haas Company, Special Products, Washington Square, Philadelphia 5, Pennsylvania (Spl54 Published in April 1960, superseding Sp-l54 dated May 1959).
  • the cross-linkable monomer should be present in the emulsion reaction in the general range of 0.2% to by Weight, of the acrylic monomer.
  • cross-linkable compounds characterized above are the methylol acrylamides, e.g.z
  • methylol acrylamides include those having more than one methylol group, such as shown in the following formulae:
  • R O-OHR wherein R is selected from hydrogen, lower alkyl and the residue of an aldehyde; R is selected from hydrogen and methyl; R is selected from hydrogen and lower alkyl; and X is selected from oxygen and sulfur.
  • acrylamide compounds may be utilized, e.g., alkylene-bisacrylamides to provide compounds of the following formulae:
  • Tse catalysts useful in activating the acid or base reactive groups are those conventionally used to activate the reaction of textile resins.
  • latent acid or base acting catalysts are utilized, that is, compounds which are acidic or basic in character under the curing conditions.
  • the most common acid acting catalysts are the organic acids, metal salts, for example, magnesium chloride, zinc nitrate and zinc fluoroborate and the amino salts, for example, monoethyanolamine hydrochloride and 2-amino-2-methyl-propanol nitrate.
  • the 'latent base acting catalyst utilized herein preferably comprises alkali-metal salts, such as alkali-metal carbonates like sodium carbonate which is neutral to moldly alkaline, for example pH of about 8.5 on the reaction under normal temperature conditions.
  • alkali-metal salts such as alkali-metal carbonates like sodium carbonate which is neutral to moldly alkaline, for example pH of about 8.5 on the reaction under normal temperature conditions.
  • Additional base acting catalysts include potassium bicarbonate, potassium carbonate, sodium silicate, alkali metal phosphates, such as sodium or potassium phosphates, barium carbonate, quaternary ammonium hydroxides and carbonates, for example, lauryl trimethyl ammonium hydroxides and carbonates and the like.
  • the amount of catalyst to be utilized is that conventionally used in activating the reaction between textile resins or polymers and hydroxy groups of cellulose, for example, up to about 5% by weight of an acid acting compound on the fabric with the preferred range being from about 1% to about 2%, based on the weight of the polymer.
  • a preferred range for the base acting catalyst is again the conventional amount and is generally between about 0.2% to about 16%, preferably about 2 to 16%.
  • the amount of catalyst to be utilized will depend in part on the temperature at which the reaction is conducted and the amount of catalyst consumed in the reaction. For example, when base catalysts are utilized and if a highly acidic group is released during the reaction, the amount of base applied to the textile material should be at least sufiicient to provide an excess of base in addition to that which is consumed by the highly acidic group.
  • the polymeric material described above is utilized in a water base emulsion as the treatment medium for sheer fabrics and garments in accordance with this invention.
  • the polymeric material is first diluted in an aqueous emulsion.
  • the polymer may be present in an amount ringing from about 0.1% to 46% solids by weight, based upon the Weight of the aqueous emulsion.
  • the polymeric rnaterial is primarily insoluble in water and will preferably be present in the emulsion in the approximate range of 0.3 to 28% solids, by weight, based upon the weight of the emulsion. Where a viscosity improver can be utilized to obtain a more uniform emulsion a higher solid content can be used.
  • catalytic initiator In order to effect cross-linking of the polymer and in order to accomplish good adhesion to the fabric or garment substrate it is necessary to add a catalytic initiator to the aqueous emulsion for the reaction.
  • catalytic intiators are preferably acid catalysts that are well-known in the textile arts, although in certain instances and depending upon the polymers or copolymers selected, a basic catalyst may be used. Among the catalysts most frequently used are oxalic acid and diammonium phoshate.
  • any of the Well-known lubricants that are conventionally used to facilitate subsequent processing of fabrics or stocking may be added to the polymeric emulsions so long as they are compatible therewith, i.e. Lanogel 41 Likewise, antifoaming agents and other additives that do not aifect the hand, stretch or other desirable characteristics of the fabric or garment may be added to the emulsion.
  • the aqueous emulsion is applied to the fabric or garment.
  • a number of stockings or other sheer fabrics or garments may be placed in a suitable container that is designed for a liquid treatment of this nature, and the articles or garments dipped and preferably submerged in the emulsion bath for a period of time ranging from a few seconds to five minutes or more.
  • the emulsion bath may be at room temperature or at a temperature ranging from about 50 F. to F.
  • an extractor for the purpose of extracting the excess liquid emulsion that may remain therein.
  • This extractor may comprise a spin dryer, for example.
  • the garments are preferably air dried for a period of time ranging approximately from an hour to 24 hours.
  • the polymeric materal will usually be present on the garment or fabric in a weight percentage varying from about 0.1 to 10%, based on the Weight of the garment or fabric.
  • this period of time due to the catalytic initiator present in the emulsion, some curing or cross-linking will take place.
  • a number of alternative boarding procedures may be used.
  • the stockings may be boarded while wet.
  • a light coating of oil or equivalent are placed on the boards with a subsequent removal of any excess oil.
  • the boards are then preheated to varying temperatures in the range of approximately 200 to 300 F., most preferably 240 to 260 F. Heating of the boards may be accomplished as in conventional boarding processes i.e., by use of steam.
  • the hose are then placed on the bot boards and are allowed to remain on the boards until all welts are dry. The period of time involved in this boarding procedure will vary from approximately one to five minutes.
  • the hose are then preferably vacuumed for a few seconds and the dry hose removed from the boards.
  • garments including hose are allowed to dry after treatment with the above described emulsion and extraction fora sufficient period of time to effect the partial cure of this polymeric material.
  • the boards are coated with a light oil such as knitting oil. In any respect, such oil is removed.
  • the hose are then placed on hot boards and allowed to remain there for a period ranging from one to five minutes at the above temperatures. Again, the dry hose are vacuumed for a few seconds and removed from the boards.
  • EXAMPLE Thirty-six grams of an n-butyl acrylate with self crosssion. The preemulsion must be stable in order to assure linking methylol groups of the type prepared above (46% uniform and consistent addition of the chemicals. This olid a ix d with one gallon of water. One dozen is done y Obtaining the maximum i c sity of the emulladies hose were put into a cotton dye bag and submerged siOIl system 11P0I1 slOW addition of the aefyletes t0 the in the emulsion and agitated for five minutes.
  • machme 1S Stopped remove hose from mathe reaction temperature began to drop (even after an chme'bemg Careful not to further Snag the hose increase in preelumsion addition rate)
  • the reaction hose board 1 f and recqrd temperature was allowed to drop to C While the picks 1n hose. Identify each pick 1n order that it W11] rate of addition of the preemulsion was slowed down not be counted agam' gradually. At this point 1 ml.
  • Th th d f treating a stocking comprising apply- P again the same procedure
  • a typical polymer of th1s type is now made by the 70 Rohm and Haas, Co. under the name E-287.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
US497519A 1965-10-18 1965-10-18 Treatment of textiles with cross-linkable acrylic polymers and the resulting products Expired - Lifetime US3476581A (en)

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Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3646749A (en) * 1969-12-24 1972-03-07 King Seeley Thermos Co Machine-washable metallized fibrous article and method of making same
US3855776A (en) * 1971-06-22 1974-12-24 Asahi Chemical Ind Synthetic thermoplastic multifilament yarns
US3910759A (en) * 1972-08-25 1975-10-07 Gaf Corp Method of treating fabrics
US3936544A (en) * 1973-05-10 1976-02-03 Feldmuehle Aktiengesellschaft Process for the manufacture of flat-shaped articles
US3950578A (en) * 1969-10-30 1976-04-13 Richard S. Keoseian Water-disintegratable sheet material
US3959569A (en) * 1970-07-27 1976-05-25 The Dow Chemical Company Preparation of water-absorbent articles
US4048369A (en) * 1975-12-12 1977-09-13 Johnson Charles E Method for controlling allergens
US4049850A (en) * 1974-05-24 1977-09-20 Kemi Oy Method of curing plastic raw materials impregnated in a porous stuff such as wood
WO1993015256A1 (en) * 1992-01-30 1993-08-05 Reeves Brothers Inc. Fabric containing graft polymer thereon
US5407728A (en) * 1992-01-30 1995-04-18 Reeves Brothers, Inc. Fabric containing graft polymer thereon
US5486210A (en) * 1992-01-30 1996-01-23 Reeves Brothers, Inc. Air bag fabric containing graft polymer thereon

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2075887A (en) * 1932-12-08 1937-04-06 Dreyfus Camille Method of finishing knit fabrics
US2157119A (en) * 1939-05-09 Method of making fabric
US2469961A (en) * 1947-04-17 1949-05-10 Lawrence W Gottschalck Knit goods and the like, and methods
US2919534A (en) * 1955-11-02 1960-01-05 Deering Milliken Res Corp Improved textile materials and methods and apparatus for preparing the same
US2954358A (en) * 1957-10-01 1960-09-27 Rohm & Haas Aqueous dispersion containing acrylic acid copolymer and aliphatic polyepoxide
US3081197A (en) * 1959-09-10 1963-03-12 Du Pont Nonwoven fabrics bonded with interpolymer and process of preparing same
US3090704A (en) * 1961-02-14 1963-05-21 Du Pont Antistatic and antisoiling agent and process for treating synthetic linear textile therewith
US3134686A (en) * 1962-04-19 1964-05-26 American Cyanamid Co Durable antistatic finish and process for applying same
US3137668A (en) * 1962-04-02 1964-06-16 Du Pont Anti-static coating composition comprising styrene sulfonate-glycidyl methacrylate polymer and sodium bisulfite

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2157119A (en) * 1939-05-09 Method of making fabric
US2075887A (en) * 1932-12-08 1937-04-06 Dreyfus Camille Method of finishing knit fabrics
US2469961A (en) * 1947-04-17 1949-05-10 Lawrence W Gottschalck Knit goods and the like, and methods
US2919534A (en) * 1955-11-02 1960-01-05 Deering Milliken Res Corp Improved textile materials and methods and apparatus for preparing the same
US2954358A (en) * 1957-10-01 1960-09-27 Rohm & Haas Aqueous dispersion containing acrylic acid copolymer and aliphatic polyepoxide
US3081197A (en) * 1959-09-10 1963-03-12 Du Pont Nonwoven fabrics bonded with interpolymer and process of preparing same
US3090704A (en) * 1961-02-14 1963-05-21 Du Pont Antistatic and antisoiling agent and process for treating synthetic linear textile therewith
US3137668A (en) * 1962-04-02 1964-06-16 Du Pont Anti-static coating composition comprising styrene sulfonate-glycidyl methacrylate polymer and sodium bisulfite
US3134686A (en) * 1962-04-19 1964-05-26 American Cyanamid Co Durable antistatic finish and process for applying same

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3950578A (en) * 1969-10-30 1976-04-13 Richard S. Keoseian Water-disintegratable sheet material
US3646749A (en) * 1969-12-24 1972-03-07 King Seeley Thermos Co Machine-washable metallized fibrous article and method of making same
US3959569A (en) * 1970-07-27 1976-05-25 The Dow Chemical Company Preparation of water-absorbent articles
US3855776A (en) * 1971-06-22 1974-12-24 Asahi Chemical Ind Synthetic thermoplastic multifilament yarns
US3910759A (en) * 1972-08-25 1975-10-07 Gaf Corp Method of treating fabrics
US3936544A (en) * 1973-05-10 1976-02-03 Feldmuehle Aktiengesellschaft Process for the manufacture of flat-shaped articles
US4049850A (en) * 1974-05-24 1977-09-20 Kemi Oy Method of curing plastic raw materials impregnated in a porous stuff such as wood
US4048369A (en) * 1975-12-12 1977-09-13 Johnson Charles E Method for controlling allergens
WO1993015256A1 (en) * 1992-01-30 1993-08-05 Reeves Brothers Inc. Fabric containing graft polymer thereon
US5407728A (en) * 1992-01-30 1995-04-18 Reeves Brothers, Inc. Fabric containing graft polymer thereon
US5486210A (en) * 1992-01-30 1996-01-23 Reeves Brothers, Inc. Air bag fabric containing graft polymer thereon
US5552472A (en) * 1992-01-30 1996-09-03 Reeves Brothers, Inc. Fabric containing graft polymer thereon

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BE688387A (enrdf_load_html_response) 1967-03-31
GB1170932A (en) 1969-11-19
NL6614653A (enrdf_load_html_response) 1967-04-19
DE1594999A1 (de) 1969-09-18
LU52181A1 (enrdf_load_html_response) 1966-12-19

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