US3717687A - Composition and method of imparting premanent press and soil release properties to fabrics - Google Patents

Composition and method of imparting premanent press and soil release properties to fabrics Download PDF

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Publication number
US3717687A
US3717687A US00127755A US3717687DA US3717687A US 3717687 A US3717687 A US 3717687A US 00127755 A US00127755 A US 00127755A US 3717687D A US3717687D A US 3717687DA US 3717687 A US3717687 A US 3717687A
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United States
Prior art keywords
textile
polymer
resin
textile resin
percent
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US00127755A
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English (en)
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E Shanley
R Doggett
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Lubrizol Corp
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Lubrizol Corp
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Classifications

    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/24—Homopolymers or copolymers of amides or imides
    • C08L33/26—Homopolymers or copolymers of acrylamide or methacrylamide
    • 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
    • Y10T442/2279—Coating or impregnation improves soil repellency, soil release, or anti- soil redeposition qualities of fabric
    • 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
    • Y10T442/2369—Coating or impregnation improves elasticity, bendability, resiliency, flexibility, or shape retention of the fabric
    • Y10T442/2393—Coating or impregnation provides crease-resistance or wash and wear characteristics

Definitions

  • I ABSTRACT Textile materials are given permanent press and soil release properties by treating them with a textile resin and a polymer of an N-sulfohydrocarbon-substituted acrylamide, preferably Z-acrylamido-Z-methylpropanesulfonic acid, and usually also with a textile resin catalyst.
  • the textile resin is normally cured on ,the fabric by heating the same to l30-200 C.
  • the principal object of the present invention is to provide improved compositions and methods for fabric treatment.
  • a further object is to provide compositions which may be applied to a fabric to impart permanent press and soil release properties.
  • compositions of this invention contain two essential components, the first of which is a textile resin.
  • Textile resins are defined in the aforementioned U.S. patents and generally include epoxy, acetal, aminoplast and similar resins, with the aminoplast resins being preferred.
  • aminoplast resin means a condensation product, usually of an amine or amide with an aldehyde, which is transformed to the 'thermoset state at temperatures of about 130200C. This product may be monomeric or polymeric.
  • aminoplast resins suitable for use in the present invention are the urea formaldehydes, e.g., propylene urea formaldehyde or dimethylol urea formaldehyde; melamine formaldehydes, e.g., tetramethylolmelamine, pentamethylolrnelamine or hexamethylolmelamine; ethylene ureas, e.g., dimethylol ethylene urea, dihydroxy dimethylol ethylene urea, ethylene urea formaldehyde or hydroxyethylene urea formaldehyde; carbamates, e.g., alkyl carbamate formaldehydes; formaldehyde-acrolein condensation products; formaldehyde-acetone condensation products; alkylolamides, e.g., N-methylolformamide, N-methylolacetamide, N- methylolacrylamide, N-methylolmethacryl
  • the second essential component of the compositions of this invention is at least one (usually only one) polymer of an N-sulfohydrocarbon-substituted acrylamide.
  • These polymers are represented by the above formula in which R is hydrogen or a lower (as defined hereinafter) alkyl radical and R is a divalent or trivalent hydrocarbon radical.
  • theterm hydrocarbon radical includes aliphatic, cycloaliphatic and aromatic (including aliphaticand cycloaliphatic-substituted aromatic and aromatic-substituted aliphatic and cycloaliphatic) radicals. It also includes cyclic radicals wherein the ring is completed through another portion of the molecule; that is, any two indicated substituents may together form a cyclic hydrocarbon radical.
  • radicals are considered fully equivalent to the hydrocarbon, alkyl, aryl, alkylene, arylene, etc., radicals and to be part of this invention.
  • substituted is meant radicals containing substituents which do not alter significantly the character or reactivity of the radical. Examples are:
  • Halide fluoride, chloride, bromide, iodide
  • Hydroxy Ether especially lower alkoxy
  • Keto Carboxy Ester especially lower carbalkoxy
  • Aminoacyl amide
  • the hydrocarbon or substituted hydrocarhon radicals in the N-sulfohydrocarbon-substituted acrylamides are free from ethylenic and acetylenic unsaturation and have no more than about 30 carbon atoms, desirably no more than about 12 carbon atoms.
  • a particular preference is expressed for lower hydrocarbon radicals, the word lower denoting radicals containing up to seven carbon atoms. Still more preferably, they are lower alkylene or arylene radicals, most often alkylene.
  • M is hydrogen or one equivalent of a cation and is usually hydrogen or alkali metal.
  • R is hydrogen or lower alkyl but is preferably hydrogen or methyl, usually hydrogen.
  • R may be any divalent or trivalent hydrocarbon radical, preferably lower alkylene or arylene and usually lower alkylene.
  • R is wherein R is hydrogen or a lower alkyl radical, R is a lower alkyl radical and the sulfonic acid group is attached to the unsubstituted methylene carbon.
  • polymers may be obtained by the polymerization, either alone or in combination with other polymerizable vinyl monomers, of the corresponding monomeric N-sulfohydrocarbon-substituted acrylamides of which the following acids, and their salts, are examples.
  • the N-sulfohydrocarbon-substituted acrylamide polymers used in the compositions of this invention may be homopolymers or copolymers, the latter containing at least about 5 percent by weight, and preferably at least about 50 percent, of N-sulfohydrocarbon-substituted acrylamide units.
  • the identity of the other monomer or monomers is not critical except that the polymer must be water-soluble or capable of forming a stable aqueous emulsion.
  • the most useful polymers are homopolymers and copolymers with 5-95 percent, preferably 5-50 percent and most desirably 5-30 percent, of an unsaturated acid (e.g., maleic acid) or a derivative thereof, especially an acrylic monomer such as acrylic or methacrylic acid or a salt or amide thereof, notably acrylamide, methacrylamide, N-methylacrylamide, diacetone acrylamide and the like.
  • unsaturated acid e.g., maleic acid
  • acrylic monomer such as acrylic or methacrylic acid or a salt or amide thereof, notably acrylamide, methacrylamide, N-methylacrylamide, diacetone acrylamide and the like.
  • the polymer may be prepared in bulk, solution, suspension or emulsion. Since the polymers are water soluble, and it is frequently convenient to prepare them in aqueous solution. Another method is to prepare an aqueous solution of the monomer or monomers and suspend the same, prior to polymerization, in a waterimmiscible solvent such as an aliphatic or aromatic hydrocarbon or halogenated hydrocarbon, removing the water after polymerization. Generally, the sulfonic acid monomer is converted to its metal salt prior to polymerization by means of a suitable alkaline reagent; however, it is also within the scope of this invention to prepare and use a polymer of the free acid. When polymerization is effected in suspension, ordinary suspending agents known to those skilled in the art are used.
  • the polymerization may be promoted by typical initiators used in aqueous systems, especially peroxides, persulfates, persulfate-bisulfite and the like. It has been found that the alkali metal salts, especially the sodium salt, of 2 -acrylamido-2-methylpropanesulfonic acid may frequently be polymerized in the absence of polymerization initiator.
  • chain transferagent It is sometimes advantageous to carry out the polymerization in the presence of a small amount of chain transferagent, which tends to cause formation of a polymer with more uniformity in molecular weight than is otherwise produced.
  • Suitable chain transfer agents are known to those skilled in the art.
  • compositions of this invention may contain additional ingredients such as textile resin curing catalysts, emulsifying agents, wetting agents, softeners and the like. While the presence of curing catalysts has previously been considered mandatory, it has been found that the N-sulfohydrocarbon-substituted acrylamide polymers used in the compositions of this invention frequently serve themselves as acidic curing catalysts and that an additional catalyst is therefore frequently unnecessary. However, it is usually advantageous to incorporate an acidic or basic catalyst depending on the curing conditions of the textile resin, in the composition.
  • the most commonly used acidic catalysts are metal salts such as magnesium chloride, zinc nitrate and zinc fluoborate, and amine salts such as monoethanolamine hydrochloride and 2-amino-2- methylpropanol nitrate.
  • metal salts such as magnesium chloride, zinc nitrate and zinc fluoborate
  • amine salts such as monoethanolamine hydrochloride and 2-amino-2- methylpropanol nitrate.
  • As basic catalysts it is desirable to use compounds which do not react under the conditions of acid catalysis but which can be activated by heat or the use of another chemical compound.
  • 11- lustrative of heat-activated basic catalysts are sodium carbonate, potassium carbonate, potassium bicarbonate, sodium silicate, sodium or I potassium phosphates, barium carbonate and quaternary ammonium hydroxides and carbonates.
  • Typical of the chemically activated type is an alkali metal sulfite, which can be decomposed into the corresponding hydrox
  • compositions of this invention will contain about 5-25 percent by weight, preferably about 5-15 percent, of the textile resin; about 1-15 percent, preferably about 1-10 percent, of the N-sulfohydrocarbon-substituted acrylamide polymer; and if a catalyst is used, about 0.5-15 percent thereof.
  • the preferred percentage range for acid catalysts is about 0.5-5 percent, and for basic catalysts about 2-16 percent.
  • N-sulfohydrocarbonsubstituted acrylamide polymers which may be used in the compositions of this invention.
  • Inherent viscosity figures are given for a solution of the polymer in 3 percent aqueous sodium chloride solution at 30C. All parts and percentages are by weight.
  • a homopolymer of 2-acrylamido-2-methylpropane-sulfonic acid prepared from a suspension in benzene of an aqueous solution of the monomer, using a hydrogen peroxide-ferrous sulfate polymerization catalyst.
  • the polymer has an inherent viscosity (0.5 percent solution) of 1.1 l.
  • a homopolymer of sodium 2-acrylamido-2 methyl-propanesulfonate prepared in benzene suspension like polymer 1 using an ammonium persulfatesodium bisulfite catalyst. Its inherent viscosity (0.5 percent solution) is 1.90.
  • a 50:50 (by weight) copolymer of sodium 2- acrylamido-2-methylpropanesulfonate and acrylic acid prepared in aqueous solution using an ammonium persulfate-sodium bisulfite catalyst and having an in herent viscosity (0.25 percent solution) of 2.33.
  • compositions of this invention are listed several compositions of this invention.
  • the balance of each composition, other than the ingredients listed, is water.
  • the textile materials which may be treated with the compositions of this invention include, without limitation, natural and synthetic textiles whether knitted, woven or non-woven, but woven materials are preferred.
  • natural materials are cotton, wool, jute, flax, viscose rayon, regenerated cellulose and the like.
  • Typical synthetic materials are polyesters such as poly(ethylene terephthalate), polyamidles such as Nylon-6 and Nylon-66, acrylic fibers such as polyacrylonitrile, and the like.
  • the invention is particularly useful with mixtures of linear polyester and cellulosic (e.g., cotton) fibers.
  • compositions of this invention may be applied to the textile material by any of several methods such as dipping, spraying, padding (which is preferred) or the like.
  • the conditions of application are adjusted to provide a predetermined wet pickup of the composition, typically about 30-100 percent. That is, the weight of liquid remaining on the fabric is 30-100 percent of the weight of the fabric.
  • N-sulfohydrocarbon-substituted acrylamide polymer separately from the textile resin, either before or after. It is generally found, however, that soil-release effectiveness is maximized if the two are applied from the same solution.
  • the treated fabric is cured at a temperature of about l30-200C. to transform the textile resin to the thermoset state. If the textile resin contains vinyl groups or other unsaturated centers, it may also be subjected to conditions promoting vinyl polymerization, typically irradiation.
  • compositions of this invention The effectiveness of the compositions of this invention is illustrated by a series of tests in which a 50:50 polyester-cotton twill trouser material is treated with said compositions under conditions so as to provide 100 percent wet pickup, mounted on tenter frames, dried 20 minutes at 80C. and cured minutes at [60C. The cured samples are rinsed and tumble dried. They are then soiled with mineral oil, salad oil and dirty motor oil, subjected to a typical laundering cycle and examined for residual oil stains. Comparison is made with a control which contains 10 percent dihydroxydimethylolethyleneurea, 1 percent zinc nitrate hexahydrate and 0.3 percent polyethoxynonylphenol surfactant, but no soil release agent. it is found that the fabric samples coated with compositions A, B, C and E retain substantially less soil than the control.
  • a composition comprising an aminoplast textile resin and at least one polymer containing at least about 5 percent by weight of units of the formula wherein R is hydrogen or a lower alkyl or substituted lower alkyl radical; R is a divalent or trivalent hydrocarbon or substituted hydrocarbon radical; M is hydrogen or one equivalent of a cation; and x is l or 2.
  • a composition according to claim 2 which also contains a textile resin catalyst.
  • composition according to claim 2 wherein the polymer contains units derived from 2-acrylamido-2- methylpropanesulfonic acid or a salt thereof.
  • composition according to claim 4 wherein the textile resin is dihydroxydimethylolethyleneurea.
  • composition according to claim 5 wherein the polymer is a homopolymer.
  • composition according to claim 6 which also contains a textile resin catalyst.
  • composition according to claim 7 wherein the catalyst is zinc nitrate or magnesium chloride.
  • a method for imparting soil release and durable press characteristics to a textile material which comprises applying thereto an aminoplast textile resin and a polymer containing at least about 5 percent by weight of units of the formula wherein R is hydrogen or a lower alkyl or substituted lower alkyl radical; R is a divalent or trivalent hydrocarbon or substituted hydrocarbon radical; M is hydrogen or one equivalent of a cation; and x is i or 2.
  • a method according to claim 9 wherein the textile material comprises linear polyester fibers.
  • R is hydrogen or methyl
  • R is a lower alkylene radical
  • x is l.
  • polymer is a homopolymer of 2-acrylamido-2-methylpropanesulfonic acid or a salt thereof.
  • polymer contains units derived from 2-acrylamido-2- methylpropanesulfonic acid.
  • a method according to claim 16 wherein the textile resin is dihydroxydimethylolethyleneurea.

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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)
  • Compositions Of Macromolecular Compounds (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
US00127755A 1971-03-24 1971-03-24 Composition and method of imparting premanent press and soil release properties to fabrics Expired - Lifetime US3717687A (en)

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US12775571A 1971-03-24 1971-03-24

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US (1) US3717687A (enExample)
JP (1) JPS544000B1 (enExample)
CA (1) CA1003596A (enExample)
DE (1) DE2212786A1 (enExample)
FR (1) FR2130542B1 (enExample)
GB (1) GB1349914A (enExample)
IT (1) IT952344B (enExample)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4008293A (en) * 1974-08-01 1977-02-15 Ppg Industries, Inc. Crosslinkable coating compositions and method of using the same
US20060045967A1 (en) * 2002-10-30 2006-03-02 The Lubrizol Corporation Adhesion promoters for glass-containing systems
US20070072971A1 (en) * 2002-10-30 2007-03-29 Manka John S Fiber dispersant-containing systems
US20090162773A1 (en) * 2005-11-11 2009-06-25 Canon Kabushiki Kaisha Polymer having sulfonic acid group or sulfonic acid ester group and amide group, and toner for developing electrostatic latent image having the polymer
US7968650B2 (en) * 2006-10-31 2011-06-28 Johnson & Johnson Vision Care, Inc. Polymeric compositions comprising at least one volume excluding polymer
CN111648131A (zh) * 2020-06-02 2020-09-11 东华大学 一种抗皱的棉纤维/聚丙烯腈纳米纤维混纺织物的制备方法

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4128631A (en) * 1977-02-16 1978-12-05 General Mills Chemicals, Inc. Method of imparting lubricity to keratinous substrates and mucous membranes
US4065422A (en) * 1977-02-16 1977-12-27 General Mills Chemicals, Inc. High slip polymer composition containing a polyacrylamido sulfonic acid salt and an alcohol
US4540510A (en) * 1984-02-13 1985-09-10 Henkel Corporation Synergistic thickener mixtures of amps polymers with other thickeners

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3236685A (en) * 1962-06-20 1966-02-22 Eastman Kodak Co Process for treating textile fibers and other shaped products with coatings
US3351618A (en) * 1964-04-17 1967-11-07 Ciba Ltd Polymerization products of carbonamides (containing sulfonamido groups) of alpha, beta-ethylenically unsaturated aliphatic carboxylic acids
US3377249A (en) * 1966-08-04 1968-04-09 Deering Milliken Res Corp Soil release of polyester containing textiles through treatment with aminoplast resins in conjunction with acrylic emulsion polymers containing at least 20% acid calculated as acrylic acid
US3405003A (en) * 1965-02-18 1968-10-08 American Cyanamid Co Soil retardant composition containing a sulfonate-polyacrylamide copolymer salt and an imidazoline plasticizer, process for treating a textile material therewith and thetreated material
US3437626A (en) * 1960-01-02 1969-04-08 Gulf Oil Corp Stabile,aqueous emulsions of ethylene copolymers
US3495930A (en) * 1962-12-06 1970-02-17 Deering Milliken Res Corp Chemically catalyzed polymerization of unsaturated monomers containing both electrophilic and nucleophilic groups on keratin fibers
US3540835A (en) * 1967-08-11 1970-11-17 Deering Milliken Res Corp Carboxylic acid group containing copolymer is applied to textile which has been treated with an aminoplast resin to improve soil release characteristics thereof

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1181419B (de) * 1962-10-20 1964-11-12 Cassella Farbwerke Mainkur Ag Verfahren zur Herstellung von vernetzbaren Mischpolymerisaten
DE1594944A1 (de) * 1966-12-27 1971-03-04 Burlington Industries Inc Textilimpraegnierung zur Erleichterung der Schmutzentfernung
US3535141A (en) * 1967-04-17 1970-10-20 Deering Milliken Res Corp Process for making sail release synthetic textile

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3437626A (en) * 1960-01-02 1969-04-08 Gulf Oil Corp Stabile,aqueous emulsions of ethylene copolymers
US3236685A (en) * 1962-06-20 1966-02-22 Eastman Kodak Co Process for treating textile fibers and other shaped products with coatings
US3495930A (en) * 1962-12-06 1970-02-17 Deering Milliken Res Corp Chemically catalyzed polymerization of unsaturated monomers containing both electrophilic and nucleophilic groups on keratin fibers
US3351618A (en) * 1964-04-17 1967-11-07 Ciba Ltd Polymerization products of carbonamides (containing sulfonamido groups) of alpha, beta-ethylenically unsaturated aliphatic carboxylic acids
US3405003A (en) * 1965-02-18 1968-10-08 American Cyanamid Co Soil retardant composition containing a sulfonate-polyacrylamide copolymer salt and an imidazoline plasticizer, process for treating a textile material therewith and thetreated material
US3377249A (en) * 1966-08-04 1968-04-09 Deering Milliken Res Corp Soil release of polyester containing textiles through treatment with aminoplast resins in conjunction with acrylic emulsion polymers containing at least 20% acid calculated as acrylic acid
US3540835A (en) * 1967-08-11 1970-11-17 Deering Milliken Res Corp Carboxylic acid group containing copolymer is applied to textile which has been treated with an aminoplast resin to improve soil release characteristics thereof

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4008293A (en) * 1974-08-01 1977-02-15 Ppg Industries, Inc. Crosslinkable coating compositions and method of using the same
US20060045967A1 (en) * 2002-10-30 2006-03-02 The Lubrizol Corporation Adhesion promoters for glass-containing systems
US20070072971A1 (en) * 2002-10-30 2007-03-29 Manka John S Fiber dispersant-containing systems
US7323083B2 (en) 2002-10-30 2008-01-29 The Lubrizol Corporation Adhesion promoters for glass-containing systems
US7728058B2 (en) 2002-10-30 2010-06-01 The Lubrizol Corporation Fiber dispersant-containing systems
US20090162773A1 (en) * 2005-11-11 2009-06-25 Canon Kabushiki Kaisha Polymer having sulfonic acid group or sulfonic acid ester group and amide group, and toner for developing electrostatic latent image having the polymer
US7935771B2 (en) * 2005-11-11 2011-05-03 Canon Kabushiki Kaisha Polymer having sulfonic acid group or sulfonic acid ester group and amide group, and toner for developing electrostatic latent image having the polymer
US7968650B2 (en) * 2006-10-31 2011-06-28 Johnson & Johnson Vision Care, Inc. Polymeric compositions comprising at least one volume excluding polymer
US8501832B2 (en) 2006-10-31 2013-08-06 Johnson & Johnson Vision Care, Inc. Polymeric compositions comprising at least one volume excluding polymer
US8883874B2 (en) 2006-10-31 2014-11-11 Johnson & Johnson Vision Care, Inc. Polymeric compositions comprising at least one volume excluding polymer
CN111648131A (zh) * 2020-06-02 2020-09-11 东华大学 一种抗皱的棉纤维/聚丙烯腈纳米纤维混纺织物的制备方法

Also Published As

Publication number Publication date
GB1349914A (en) 1974-04-10
CA1003596A (en) 1977-01-11
IT952344B (it) 1973-07-20
JPS544000B1 (enExample) 1979-02-28
DE2212786A1 (de) 1972-09-28
FR2130542B1 (enExample) 1976-06-11
FR2130542A1 (enExample) 1972-11-03

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