US3167448A - Process of treating fabrics with ethylene carbonate and article produced therefrom - Google Patents

Process of treating fabrics with ethylene carbonate and article produced therefrom Download PDF

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Publication number
US3167448A
US3167448A US133299A US13329961A US3167448A US 3167448 A US3167448 A US 3167448A US 133299 A US133299 A US 133299A US 13329961 A US13329961 A US 13329961A US 3167448 A US3167448 A US 3167448A
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United States
Prior art keywords
percent
acrylonitrile
ethylene carbonate
fabrics
fabric
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US133299A
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English (en)
Inventor
Julian J Hirshfeld
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Monsanto Co
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Monsanto Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority to BE621636D priority Critical patent/BE621636A/xx
Priority to NL282288D priority patent/NL282288A/xx
Application filed by Monsanto Co filed Critical Monsanto Co
Priority to US133299A priority patent/US3167448A/en
Priority to GB31939/62A priority patent/GB988453A/en
Priority to SE9080/62A priority patent/SE312117B/xx
Priority to FR907412A priority patent/FR1331247A/fr
Priority to DE19621444093 priority patent/DE1444093A1/de
Priority to CH1005762A priority patent/CH392452A/fr
Application granted granted Critical
Publication of US3167448A publication Critical patent/US3167448A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
    • D06M15/6436—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain containing amino groups
    • 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
    • D06M13/10—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 oxygen
    • D06M13/224—Esters of carboxylic acids; Esters of carbonic acid
    • D06M13/232—Organic carbonates
    • 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
    • Y10T428/23907—Pile or nap type surface or component
    • Y10T428/2395—Nap type surface
    • 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
    • Y10T428/23907—Pile or nap type surface or component
    • Y10T428/23986—With coating, impregnation, or bond

Definitions

  • This invention is concerned with the treatment of the raised surface of woven, non-woven and knitted synthetic fabrics to prevent distortion of the raised surface due to normal wearing and laundering conditions. More specifically, this invention is concerned with preventing the matting, shedding and pilling of the nap of acrylic fabrics after subjecting these fabrics to normal laundering and wearing conditions, as well as preserving a soft hand.
  • An object of this invention is to provide a method by which the nap of synthetic fabrics are stabilized against normal wearing and laundering conditions.
  • Another object of this invention is to provide a stabilizing agent to prevent excessive matting, pilling and shedding of the nap of synthetic fabrics.
  • Another object of this invention is to provide a stabilizing agent for the nap of synthetic fabrics which gives a soft hand.
  • Another object of this invention is to provide a stabilizing agent for the nap of synthetic fabrics which does not deleteriously affect the color.
  • Another object of this invention is to provide a stabilizing agent for the nap of acrylonitrile fabrics which renders the fabrics free of excessive matting, pilling and shedding under normal laundering conditions as well as normal wearing conditions.
  • Another object of this invention is to provide permanent stability of high pile fabrics against matting, pilling and shedding.
  • the objects of this invention are generally accomplished by applying an aqueous solution of ethylene carbonate to the nap or raised surface of synthetic fabrics, either woven, non-woven or knitted. Thiscompound is applied by the conventional padding method.
  • a silicone emulsion is also padded into the fabrics. The use of the silicone' emulsion results in an acceptable soft hand when used in conjunction with the ethylene carbonate.
  • an anti-static agent such as Aston 108, which is a polyamine resin such as diethylenetriamine crossed-linked with polyethylene glycol diiodide or an epoxy resin, may be used inv conjunction with the silicone emulsion and ethylene carbonate which will give excellent protection against static electricity.
  • the fabric maybe treated with the above agents and a water repellent-agent such as Phobotex F.T.C., a melamine derivative, which will not afiect the hand or color and will give excellent resistance to water penetration.
  • a water repellent-agent such as Phobotex F.T.C., a melamine derivative, which will not afiect the hand or color and will give excellent resistance to water penetration.
  • Phobotex F.T.C. a melamine derivative
  • the synthetic fabrics were mapped and then treated with an aqueous solution of ethylene carbonate in the range of a 0.05 percent solution to a 50 percent solution with the preferred solution being a 0.5 percent to a 2.0 percent solution.
  • R and R being generally aliphatic radicals and n being from 1 to oowere added to improve the hand of the treated and napped synthetic fabric.
  • An aqueous emulsion of the silicone of from 0.2 percent to 5 percent may be used with the preferred being a 1 percent to a 2 percent emulsion. More than a 5 percent emulsion may be used, but there is no improvement in the hand above the 5 percent emulsion and only increases the cost.
  • the napped and treated fabrics were then heated in a conventional fabric drying apparatus, such as a chain dryer, to evaporate the water and to cure the softening agent-the silicone; in addition, this stabilizing compound, ethylene carbonate, is concentrated at the points of intersection of the fibers in the nap to form a durable bond between and among themselves.
  • the period of time the fabrics were heated ranged from 5 minutes to 60 minutes, with the preferred being 20 minutes, at a temperature of 240 F. to 300 F., with the preferred temperature being 280 F. If an aqueous ethylene carbonate solution is used alone. then the exact temperature is immaterial as long as the fabrics so treated are dried; however, the temperature must not go to the degradation point of the acrylic fibers, 350 F.
  • the napped fabrics were then withdrawn from the drying apparatus, and it was found that the hand was of acceptable softness and the color was unaffected.
  • the stabilizing compound and softening agent were added onto the nap by the conventional padding method which is known in the textile field.
  • Other agents such as water repellents and anti-static agents may have been added to the original padding bathwhich would have resulted in giving the mapped fabric, not only stability to laundering and wearing, but a softhand and permanent anti-static and water repellent properties.
  • the polymeric materials which may be employed in the practice of the present invention, are polyacrylonitrile, copolymers, including binary and ternary polymers containing at least percent by weight of acrylonitrile in the polymer molecule, or a blend comprising polyacrylonitrile or copolymers comprising acrylonitrile with from 2 to 50 percentof another polymeric material, the blend having an overall polymerized acrylonitrile content of at least 80 percent by weight.
  • the preferred polymers employed in the instant invention are those containing at least 80 percent of acrylonitrile, generally recognized as the fiber-forming acrylonitrile polymers, it will be understood that the invention is likewise applicable to polymers containing less than 80 percent acrylonitrile.
  • the acrylonitrile polymers containing less than 80 percent acrylonitrile are useful in forming films, coating compositions, molding operations, lacquers, etc., in all of which applications the alleviation of undesirable color is extremely important.
  • the polymer may be a copolymer of from 80 to 98 percent acrylonitrile and from 2 to 20 percent 7 tion.
  • Suitable mono-olefinic monomers include acrylic, alpha-chloroacrylic and methacrylic acids; the acrylates, such as methylmethacrylate, ethylmethacrylate, butylmethacrylate, methoxymethyl methacrylate, beta-chloroethyl methacrylate, and the corresponding esters of acrylic and alpha-chloroacrylic acids; vinyl chloride, vinyl fiuoride, vinyl bromide, vinylidene chloride, l-chloro-l-brmo-ethylene; methacrylonitrile; acrylamide and methacrylarnide; alpha-chloroacrylamide; or monoalkyl substitution products thereof; methylvinyl ketone; vinyl carboxylates, such as vinyl acetate, vinyl chloroacetate, vinyl propionate, and vinyl stearate; N-vinylimides, such as N-vinylphthalimidiol, ethylene, ethylene ethylene, and the corresponding esters of acrylic and al
  • the polymer may be a ternary or higher interpolymer, for example, products obtained by the interpolymerization of acrylonitrile and two or more of any of the monomers, other than acrylonitrile, enumerated above. More specifically, and preferably, the ternary polymer comprises acrylonitrile, methacrylonitrile, and 2-vinylpyridine.
  • the ternary polymers preferably contain from 80 to 98 percent of acrylonitrile, from 1 to percent of a vinylpyridine or a l-vinylimidazole, and from 1 to 18 percent of another substance such as methacrylonitrile or vinyl V chloride.
  • the polymeric material when it comprises a blend, it will be a blend of a copolymer of 90 to 98 percent acrylonitrile and from 2 to 10 percent of another monomer-olefinic monomer, such as vinyl acetate, which is not receptive to dyestuff, with a sufficient amount of a copolymer of from 10 to 70 percent of acrylonitrile and from 30 to 90 percent of a vinylsubstituted tertiary heterocyclic amine, such as vinylpyridine or l-vinylimidazole, to give a dyeable blend having an overall vinyl-substituted tertiary heterocyclic amine content of from 2 to 10 percent, based on the weight of the blend.
  • a copolymer of 90 to 98 percent acrylonitrile and from 2 to 10 percent of another monomer-olefinic monomer such as vinyl acetate, which is not receptive to dyestuff
  • Example 1 A swatch of nappedfabric composed of synthetic, linear acrylonitrile polymers was padded with an aqueous solu- Example 2
  • Example 3 A swatch of napped acrylic fabric composed of fibers of a blend of 88 percent or one copolymer of 94percent acrylonitrile and 6 percent vinyl acetate and 12' percent of another copolym er composed of 5 0 percent acrylonitrile and percent methyl vinyl pyridine was padded with a 0.50 percent aqueous solution of ethylene carbonate.
  • Example 4 A swatch of napped fabric composed of fibers of 92 percent acrylonitrile and 8 percent vinyl acetate was padded with a 0.25 percent aqueous solution of ethylene carbonate. 1 The swatch was then placed in a drying oven and heated for 20 minutes at 220 F. It was then removed and allowed to cool, after which the swatch was laundered five consecutive times under normal laundering conditions. The hand remained very soft and the color was not affected. In addition there was no excessive amount of matting, pilling or shedding.
  • Example 5 A swatch of napped fabric composed of fibers of 92 percent acrylonitrile and 8 percent vinyl acetate was padded with a 0.10 percent aqueous solution of. ethylene carbonate. The swatch was then placed in a drying oven and heated for 20 minutes at 220 F. It was then removed and allowed to dry, after which the swatch was laundered. five consecutive times under normal laundering conditions. The hand remained very soft and the color was not affected. :In addition there was no exces .sive amount of matting,pilling' or shedding.
  • Example 6 percent of sodium bisulfate, a catalyst.
  • the swatch was then placed in a drying oven and heated for 20 minutes at 220 F. The temperature was then raised to 280 F. for ten minutes to cure the silicone. It was then removed and allowed to cool, after which the swatch was laun dered for five consecutive times under normal laundering It was then removed and allowed to cool, after conditions. The hand remained very soft and the color was not affected. In addition there was no excessive amount of matting, pillingor shedding.
  • Example 7 A swatch of napped fabric composed of fibers of 92 percent acrylonitrile and 8 percent vinyl acetate was padded with an aqueous solution composed of 0.5 percent ethylene carbonate, 2.0 percent silicone resin and 0.2 7
  • the swatch' was then placed in a drying, oven where it was heated for 20 minutes at 220 F. The temperature of the oven was then raised to 280 F. for minutes to cure the silicone resin. It was then removed from the oven and allowed to cool, after which the swatch was laundered five consecutive times under normal laundering conditions. The hand remained very soft and the color was not affected. In addition there was no excessive amount of matting, pilling or shedding.
  • the stabilizing compound of this invention it is possible to treat napped fabrics composed of acrylic fibers so that they may be laundered many times and their hand, color and physical properties, such as matting, pilling and shedding will not be appreciably changed from their original conditions.
  • An article composed of the napped fabric of fibers of synthetic linear acrylonitrile, ethylene carbonate as a bonding agent at the point of intersection of the fibers in the nap and a silicone resin as a softening agent.
  • the article of claim 1 in which the fabric is composed of fibers of at least 80 percent acrylonitrile and up to 20 percent of another copolymerizable mono-olefinic monomer.
  • a method of stabilizing the nap of fabrics composed of fibers of synthetic linear polymers of acrylonitrile comprising impregnating the napped fabric with an aqueous solution of ethylene carbonate and a silicone resin in which the ethylene carbonate as a bonding agent is used in an amount of from 0.05 percent to 50 percent by weight of the solution, drying said fabric and curing the silicone resin by heating said fabric at a temperature of from 240 F. to 300 F. for 5 to 60 minutes.
  • the fibers are selected from the group consisting of a fiber of 94 percent acrylonitrile and 6 percent vinyl acetate and a blend of 88 percent of one copolymer of 94 percent acrylonitrile and 6 percent vinyl acetate and 12 percent of another copolymer composed of 50 percent acrylonitrile and 50 percent methyl vinyl pyridine.
  • a method of stabilizing the nap of fabrics composed of fibers of at least 80 percent acrylonitrile and up to 20 percent of another copolymerizable mono-olefinic monomer comprising impregnating the napped fabric with an aqueous solution of ethylene carbonate in which ethylene carbonate acts as a bonding agent at the point of intersection of the fibers in the nap to form a durable bond, with the amount of ethylene carbonate being 0.5 percent to 2.0 percent by weight of the solution, and drying said fabric.
  • a method of stabilizing the nap of fabrics composed of fibers of at least 80 percent acrylonitrile and up to 20 percent of another copolymerizable mono-olefinic monomer comprising impregnating the napped fabric with an aqueous solution of ethylene carbonate, in the range of a 0.05 percent to a 50 percent solution, with ethylene carbonate acting as a bonding agent at the point of intersection of the fibers in the nap to form a durable bond, and a silicone resin emulsion in the range of 0.2 percent to 5 percent solution, drying said fabric and ouring the silicone resin by heating said fabric to 280 F. for 10 minutes.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
US133299A 1961-08-23 1961-08-23 Process of treating fabrics with ethylene carbonate and article produced therefrom Expired - Lifetime US3167448A (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
BE621636D BE621636A (en:Method) 1961-08-23
NL282288D NL282288A (en:Method) 1961-08-23
US133299A US3167448A (en) 1961-08-23 1961-08-23 Process of treating fabrics with ethylene carbonate and article produced therefrom
GB31939/62A GB988453A (en) 1961-08-23 1962-08-20 Improvements in the treatment of napped polyacrylonitrile fabrics
SE9080/62A SE312117B (en:Method) 1961-08-23 1962-08-21
FR907412A FR1331247A (fr) 1961-08-23 1962-08-21 Perfectionnements au traitement des étoffes synthétiques, en particulier des étoffes acryliques
DE19621444093 DE1444093A1 (de) 1961-08-23 1962-08-22 Verfahren zur Stabilisierung der Aufrauhung oder des Flors von Textilwaren
CH1005762A CH392452A (fr) 1961-08-23 1962-08-23 Procédé de stabilisation de la couche de poils d'étoffes en fibres acryliques

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US133299A US3167448A (en) 1961-08-23 1961-08-23 Process of treating fabrics with ethylene carbonate and article produced therefrom

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US3167448A true US3167448A (en) 1965-01-26

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US133299A Expired - Lifetime US3167448A (en) 1961-08-23 1961-08-23 Process of treating fabrics with ethylene carbonate and article produced therefrom

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US (1) US3167448A (en:Method)
BE (1) BE621636A (en:Method)
CH (1) CH392452A (en:Method)
DE (1) DE1444093A1 (en:Method)
GB (1) GB988453A (en:Method)
NL (1) NL282288A (en:Method)
SE (1) SE312117B (en:Method)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3399079A (en) * 1964-09-25 1968-08-27 American Cyanamid Co Antistatic fiber blend
US3431159A (en) * 1964-06-17 1969-03-04 David Gordon Manufacture of mouldings from acrylonitrile copolymers
US3488217A (en) * 1968-02-29 1970-01-06 Du Pont Process for imparting a soft feel to textile fiber and the resulting fiber
US3530214A (en) * 1967-02-24 1970-09-22 Julius Hermes Method for treating textile materials to uniformly set their shape
US4290766A (en) * 1980-09-22 1981-09-22 Milliken Research Corporation Chemically sculpturing acrylic fabrics and process for preparing same

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2588365A (en) * 1949-11-10 1952-03-11 Dow Corning Method of rendering fabrics waterrepellent and product resulting therefrom
US2734041A (en) * 1953-03-13 1956-02-07 Compositions of matter comprising

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2588365A (en) * 1949-11-10 1952-03-11 Dow Corning Method of rendering fabrics waterrepellent and product resulting therefrom
US2734041A (en) * 1953-03-13 1956-02-07 Compositions of matter comprising

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3431159A (en) * 1964-06-17 1969-03-04 David Gordon Manufacture of mouldings from acrylonitrile copolymers
US3399079A (en) * 1964-09-25 1968-08-27 American Cyanamid Co Antistatic fiber blend
US3530214A (en) * 1967-02-24 1970-09-22 Julius Hermes Method for treating textile materials to uniformly set their shape
US3488217A (en) * 1968-02-29 1970-01-06 Du Pont Process for imparting a soft feel to textile fiber and the resulting fiber
US4290766A (en) * 1980-09-22 1981-09-22 Milliken Research Corporation Chemically sculpturing acrylic fabrics and process for preparing same

Also Published As

Publication number Publication date
CH392452A (fr) 1965-02-15
NL282288A (en:Method) 1900-01-01
DE1444093A1 (de) 1968-11-07
GB988453A (en) 1965-04-07
BE621636A (en:Method) 1900-01-01
SE312117B (en:Method) 1969-07-07

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