US3100674A - Process for shrink-proofing proteinaceous textile materials and the product therefrom - Google Patents

Process for shrink-proofing proteinaceous textile materials and the product therefrom Download PDF

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US3100674A
US3100674A US858028A US85802859A US3100674A US 3100674 A US3100674 A US 3100674A US 858028 A US858028 A US 858028A US 85802859 A US85802859 A US 85802859A US 3100674 A US3100674 A US 3100674A
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copolymer
textile
weight
textile materials
shrink
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US858028A
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Fred H Steiger
Hugo A Alps
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Rohm and Haas Co
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Rohm and Haas Co
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Priority to US858028A priority Critical patent/US3100674A/en
Priority to GB35418/61A priority patent/GB998188A/en
Priority to GB4231260A priority patent/GB968385A/en
Priority to FR846344A priority patent/FR1275792A/fr
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F20/00—Homopolymers and 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 a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/52—Amides or imides
    • C08F20/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
    • C08F20/58—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing oxygen in addition to the carbonamido oxygen, e.g. N-methylolacrylamide, N-acryloylmorpholine
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F20/00—Homopolymers and 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 a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F20/62—Monocarboxylic acids having ten or more carbon atoms; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—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 a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • D—TEXTILES; PAPER
    • D04—BRAIDING; LACE-MAKING; KNITTING; TRIMMINGS; NON-WOVEN FABRICS
    • D04H—MAKING TEXTILE FABRICS, e.g. FROM FIBRES OR FILAMENTARY MATERIAL; FABRICS MADE BY SUCH PROCESSES OR APPARATUS, e.g. FELTS, NON-WOVEN FABRICS; COTTON-WOOL; WADDING ; NON-WOVEN FABRICS FROM STAPLE FIBRES, FILAMENTS OR YARNS, BONDED WITH AT LEAST ONE WEB-LIKE MATERIAL DURING THEIR CONSOLIDATION
    • D04H1/00—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres
    • D04H1/40—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres from fleeces or layers composed of fibres without existing or potential cohesive properties
    • D04H1/58—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres from fleeces or layers composed of fibres without existing or potential cohesive properties by applying, incorporating or activating chemical or thermoplastic bonding agents, e.g. adhesives
    • D04H1/587—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres from fleeces or layers composed of fibres without existing or potential cohesive properties by applying, incorporating or activating chemical or thermoplastic bonding agents, e.g. adhesives characterised by the bonding agents used
    • 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

Definitions

  • This invention relates to the treatment of textile materials formed of interlocked yarns of protein-containing fibers and to the products thereof. It relates more particularly to a process of treating woven and knitted textile materials comprising scale surfaced protein fibers, such as wool and wool-containing fabric, whereby the textile materials are stabilized against shrinkage.
  • An object of this invention is to apply certain aqueous dispersions of resins to protein-containing woven and knitted textile materials which, after heating, markedly reduce the tendency of the materials to shink or render them substantially shrink-proof.
  • Another object is to provide a process for shrink-proofing of textile materials formed of interlocked yarns containing scale-surfaced protein fibers, whether of natural or artificial origin, through the use of the aforesaid dispersions. It is an object to shrink-proof the textiles without adversely affecting such other properties of the textile as wearing qualities, tensile strength, dye-fastness qualities, or hand.
  • Still another object is to produce protein-containing textile materials, particularly woolen fabrics, which have a much reduced tendency to shrink and which also retain the desirable characteristics which are associated with woolen fabrics.
  • textile materials of proteinaceous types While this invention is principally concerned with improvements of, and more particularly the reduction of shrinkage and/0r complete stabilization of, textile materials of proteinaceous types, and while the invention is described primarily in terms of wool-containing textiles, the invention embraces the treatment of other protein containing woven and knitted.
  • textile materials such as those made of or containing silk, mohair, fur, Aralac and other synthetic fibers which are produced from casein, soybeans, zein, collagen, et cetera, and especially scalesurfaced protein fibers of either natural or artificial origin.
  • Such textile materials may contain only one kind of proteinaceous fiber or a mixture of such fibers with other natural or synthetic fibers such as of cotton, linen, rayon, nylon, or polymers of acrylonitrile.
  • certain polymers are capable of improving the abrasion resistance of the protein-containing textiles and are highly effective for the stabilization of textiles comprising at least 40% by weight of scale-surfaced protein fibers, such as wool. More particularly, it has been discovered that certain linear addition copolymers containing N-methylolamide groups with or without other coreactive groups, in certain proportions, when applied to protein-containing woven and knitted textile fabrics and cured by heating at elevated temperatures, impart resistance to normal laundering operations such as may be performed with modern detergents of the type represented by Tide, All, and Fab, as well as resistance to dry-cleaning by chlorinated hydrocarbons such as carbon tetrachloride. By coreactive is meant groups which react with the N- methylola-mide groups.
  • the linear addition copolymers applied in accordance with the present invention are water-insoluble copolymers of a mixture of copolymerizable monoethylenically unharshnessto the fabric.
  • Other treatments are not permanently effective and may even cause an ultimate increase in shrinkage.
  • Still other shrink-proofing methods are difiicult to apply with uniformity and create hazards to the workers involved in their applications. Some treatments reduce the wash-fastness of dyed fabrics.
  • the process of treating the woven and knitted textile materials in accordance with the invention comprises impregnating them with an aqueous dispersion of a waterinsoluble linear emulsion copolymer of the kind described in detail below and then heating the textiles at a temperature which is "at least as high as 212 F., but which is lower than the charring point of the textile.
  • a chemical reaction is saturated molecules comprising '(A) 0.5 to 6% (preferably lto 4%) by weight of N-methylolacrylamide, N- methylolmethacrylamide, or of a mixture thereof, which compounds may be represented by the generic formula GONHOHzOH (I) in which n is an integer having a value of l to 2, and (B) zero to 6% by weight of a monomer which contains a group coreactive with the N-methylolamide group.
  • the copolymers should have an apparent second order transition temperature, T which is not over 0 C.
  • the molecular weight may be from 100,000 to 10,000,060.
  • the T value referred to herein is the transition temperature orinflection temperature which is found by plotting the modulus of rigidity against temperature. A convenient method for determining modulus of rigidity is described by I. Williamson, British Plastics 23, 87-90, 102 (September 1950). The T value here used is that determined at 306 kg./cm.
  • the coreactive monomers are those which contain reactive hydrogen atoms in amide groups (CONH amino groups (-NH hydroxyl groups (-OH), and carboxyl or carboxylate groups (COOH).
  • Examples include acrylic acid, methacrylic acid, itaconic acid, acrylamide, methacrylamide, ⁇ i-hydroxye-thyl aorylate or methacrylate, N-B-hydroxyethyl-aorylamide or '-methacrylamide, B-hydroxypropyl acrylate or methacrylate, N- fl-hydroxypropyl-acryl amide or -methacrylamide, fl-hydroxyethyl or fi-hydroxypropyl vinyl ether or vinyl sulfide, and B-aminoethyl vinyl ether or ⁇ fi-aminoethyil acrylate.
  • the nitrogen atoms of the amide and amino groups may be secondary atoms, i.e., they may have onlyone O O O R (II) wherein n is an integer having a value of 1 to 2, R is an alkyl group having 1 to 18 carbon atoms when n is 1 and 4 to 18 carbon atoms when n is 2.
  • esters are butyl methacrylate, methyl acrylate, ethyl acrylate, butyl 'acrylate, t-octyl acrylate and methacrylate, and ootadecyl acrylate and methacryla te.
  • the proportion of any such monomer used in the copolymer is limited to that which will produce, with the other monomers used in the particular copolymer, such as ethyl aorylate, methyl acrylate, butyl acrylate, or octyl acrylate or methacrylate, a T value of C. or less.
  • the N-methylolamide of Formula l may be used in greater amounts than the 6% upper limit mentioned and the core active monomer may be used in greater amounts than the 6% upper limit mentioned above, but generally the total of N-methylol'amide units and of units coreaotive therewith should'not exceed 25% by weight and the optimum results are obtained when these monomers are used in the ranges heretofore given. Higher proportions of the compound of Formula I tend to make the product excessively stiff and higher proportions of the coreaotive compound tend to reduce the wash-resistance of the products.
  • the preferred 'copolymers are those employing N-methylolacrylamide. In general, these copolymers are twice as efiicient for a given content of the monomer of Formula I, other components and all conditions being the same, as the copolymers obtained from N-methylolmethacrylamide.
  • the N-methylolamide copolymers may be produced by conventional emulsion polymerization procedures employing a suitable emulsifier such as a non-ionic, cationic, or an anionic emulsifier or mixtures of a non-ionic with a cationic or an anionic emulsifier in conjunction with a free-radical initiator which may, if desired, be a component of any of the well-known redox systems.
  • emulsifiers that may be used include sodium lauryl sulfate, t-octylphenoxypolyethoxyethanols containing from about to 50 oxyethylene units per molecule, and lauryl pyridinium chloride.
  • the amount of emulsifier may range from about /2% to 6% on the weight of monomers.
  • Any free-radical initiator such as azodiisobutyronitrile, t-butyl hydroperoxide, and ammonium or potassium persulfates may be employed.
  • the proportion of initiator may be from 0.1% to 2% on the weight of monomers.
  • the polymers used in the present invention may also be graft or block copolymers wherein one or more, but not all, of the monomers are first polymerized and then one or more other monomers are copolymerized with the first polymer obtained.
  • methacrylamide or N- methylolacry lamide may first be homopolymerized or copolymerized with one or more, but less than all, of the comonomers to be introduced into the ultimate copolymer,.and then the last monomer or monomers are added to the system and copolymerized or grafted on to the first homopolymer or copolymer formed.
  • the same procedure may be used in reverse order to graft the methacrylamideor N-methylolacrylamide on .to a previouslyformed homopolymer or copolymer of other monomeric units.
  • a plurality of monomeric units may be introduced in succession and the methacrylamide or N- 4 methylolacrylamide may be introduced at the beginning, at any intermediate stage, or at the end as desired.
  • the proportion of the polymer that is applied to the fabric may vary widely, such as from 1 to by weight of the fabric, a proportion of 3 to 10% being preferred.
  • the hand or feel of the fabric may be varied widely depen'ding on the polymer selected.
  • a softer and more lubricous hand may be imparted by copolymerizing with a comonomer of such character that it introduces a long-chain fatty group into the copolymer.
  • the N-methylolamide monomer may be copolymerized with acrylic, methacrylic, or itaconic esters of alcohols containing from 1 to 18 carbon atoms, the longer the chain of the alcohol, the more lubricous the hand.
  • the dispersion is deposited on the textile material by such means as exhausting, spraying, or dipping.
  • ' textile material should be saturated and impregnated by I up or take up and then retain suflicient dispersion to provide from 1 to about 20%, and preferably from 3% to 10% of the copolymer, based on the weight of the dry stabilized textile.
  • the impregnated textile material must then be heated at a temperature between 212 F. and 400 F. for a period of about one-half minute to 30 minutes, the higher the temperature, the shorter the period required.
  • a flash cure at temperatures above 400 -F. even up to 500 F. for short periods of five to ten seconds may be employed.
  • the time and temperature should not be such as to damage the fabric.
  • this heating is effected at a temperature from 240 F. (for about 10 to 15 minutes) to about 310 F. (for about 5 to 10 minutes), and it is believed that it effects some chemical reaction involving the polymer and possibly the textile.
  • the heating sets the polymer on the textile, and reduces shrinkage and/or imparts full dimensional stability thereto.
  • Drying of the treated textile and the heat-treatment which effects the chemical reaction can be carried out simultaneously or concurrently in one step, orthe textile can be substantially or completely dried at a conveniently lower temperature and then heated later at the higher temperature.
  • the optimal length of the heating period depends on the particular temperature which is employed, on the particular copolymer, and on the quantity thereof which is on the textile. But in any case the heat-treatment does not require a long period and is usually measured in minutes, generally one to thirty minutes and preferably about live to fifteen minutes.
  • the most satisfactory time of heating for any particular combination of dispersions and textile is readily determined by heating pieces of the impregnated textile for varying lengths of time at a given temperature and then measuring the resultant stabilization of the individual pieces by means of a wet-washing test.
  • aqueous dispersions of the copolymers of the monomers of Formula I are generally colorless, non-toxic, non-irritating, and free of any disagreeable odor, before, during, and after application to the fabric. They are easily applied, involve no fire hazard, and require no solvent recovery system. They do not alter the color of the wool, whether dyed or not.
  • the finished fabrics are generally not deleteriously altered, and are frequently improved, in respect to their resistance to deterioration on exposure to sunlight, heat, and normal ageing conditions.
  • acidic substances or salts that are substantially neutral at ordinary temperature but liberate acid on heating during the curing stage, such as aunmonium phosphate, ammonium thiocyanate, hydrochloric or other acid salts of a hydroxy aliphatic amine including 2-methyl-2-amino-l-propanol, Z-methyl-Zamino 1,3 propanediol, tris(hydroxymethyDaminomethane, 2-phenyl-2-amino-lpropanol, Z-methyl-Z-amino-lpentanol, 2-aminobutanol, triethanolamine, 2-aijsigo-2- ethyl-l-butanol, also ammonium chloride, pyridine hydrochloride, benzyldimethylamine oxalate.
  • acid or acidic substance based on the weight of the pad liquor.
  • the products obtained employing the aqueous dispersion of the N-methylolamide-containing copolymers of the present invention have good resistance to laundering and dry-cleaning when the copolymer is used as the sole stabilizing agent and is cured in the manner stated here'inabove.
  • Such products are also free of any tendency to become discolored on chlorination and ironing.
  • the copolymer of the present invention may be employed in conjunction with a thermosetting resin condensate such as an aminoplast or polyepoxide.
  • the amount of such condensate that may be included in the binder compositions may be as high as 20% by weight of the copolymer, a proportion of 3 to being preferred when such condensate is used.
  • aminoplast condensates which may be employed are the low molecular weight or monomeric reaction products of formaldehyde with urea, thiourea, biuret, or other homologs or derivatives thereof, such as N,N-ethyleneurea, N,N-ethyleneurea, N,N-dimet-hylurea, N,N'- diethylurea, N,Ndirnethoxymethylurea, N,N-dimethoxymethylurea, N,N-diethoxyethyl-urea, tetramethoxymethylurea, tetraethoxyethylurea.
  • the extent of condensation of these resinaforming aminoplast condensates is such that they are still soluble in water or self-dispersible therein to a colloidal O O (V) where m is an integer having a value of 2 to 4, and z is a number having an average value of 1 to 5.
  • the water-insoluble but sel-f-dispersible condensates containing epoxide groups include the compounds of Formula IV above wherein 1 has an average' value of 5 to 10 and also compounds of Formula VI:
  • auxiliary substances are not necessary to produce efiective stabilization in a practical manner. However, in some instances, their use enhances the stabilization obtainable or enables stabilization to be eifected at less expense.
  • the stabilizing copolymer composition may be preferentially applied, if desired, to portions of the wool fabric, it is characteristic of the compositions of the present invention that, if such preferential treatment is not desired, substantially uniform distribution may be obtained because of the reduced tendency of the compositions after initial distribution throughout the body of the fibrous product to migrate to the surfaces thereof during drying.
  • the treated textiles are characterized by greater resistance to abrasion and/or reduced shrinkage and, in many cases, fully practical dimensional stability against laundering, by which is meant that they are substantially shrinkproof. They do not stiffen, degrade or discolor on ageing or on exposure to ultraviolet light as do comparable textiles which have been treated, for example, with latices of, butadiene copolymers. They also retain dyeability with acid dyestuffs and are resistant to loss of stabilization when subjected to hot acid baths during dyeing.
  • the effectiveness of the dispersions exemplified below in stabilizing wool was determined by impregnating measured pieces of flannel with them, drying, and heating the impregnated pieces of flannel at a temperature of 240 F. or higher, laundering the pieces in hot water, then drying them and measuring the shrinkage.
  • the pieces of flannel were padded with a pad liquor of the resin dispersion which was so adjusted in solids-content as to provide the desired amount of resins-solids (l to 20% based on the weight of the dry flannel) at a pick was maintained at 140 F.
  • the values of shrinkage are given as percentagereduction in the initial area after taking into account any inherent residual shrinkage in the initial fabric that may be present as a result of previous drying under tension, and is removable by simply wetting and drying. In other Words, the shrinkage values hereinbelow are obtained by subtracting relaxation shrinkage from the actual shrinkage measured.
  • Example 1 An aqueous dispersion containing 45% by weight of an emulsion copolymer of about 0.8% of acrylamide, 98% of ethyl acrylate, and 1.2% of N-methylolacrylamide was prepared by emulsion copolymer-ization.
  • the resin dispersion was diluted to a 5% concentration of the resin content and /z% of ammonium chloride was added and applied to a wool flannel as described above. Above drying 10 minutes at 240 F., followed by curing for 10 minutes at 300 -F., it was found that the proportion of copolymer applied to the fabric was about 3 /z% of the Weight of the fabric.
  • the shrinkage of the treated fabric after the five-hour Wash described hereinabove was 3%.
  • Example 2 An aqueous dispersion containing 46% by Weight of an emulsion copolymer of about 1.7% of acrylamide, 47.9% of ethyl aorylate, 48.0% of Z-ethylhex'yl acrylate, and 2.4% of N-methylolacrylamide was prepared by emulsion copolymerization. The resin dispersion was diluted to a 6% concentration of the resin content. Then 0.5% ammonium chloride and 0.1% of t-octylphenoxypolyethoxyethanol having an average of about ten oxyet-hylene units per molecule were added and applied to an unbleached wool flannel as described above.
  • Example 3 Results similar to those obtained in Example 2(a) were obtained by application in the same way of a copolymer of 1.7% of acrylamide, 95.9% ethyl acrylate, and 2.4% of N-met-hylolac-rylamide.
  • Example 4 Results similar to those obtained in Example 2(a) were obtained by application in the same way of 7% of the weight of the fabric of a copolymer of about 96% of ethyl tacrylate and 4% of N-methylolmethacrylamide.
  • Example 5 The procedure of Example 2 was repeated with good reduction of shrinkage, using an emulsion copolymer of 46% of ethyl acrylate, 48% of butyl acrylate, and 6% of in which formulas n us an integer having a value of 1 to 2, and R is an alkyl group having 1 to 18 carbon atoms when n is 1 and 4 to 18 carbon atoms when n is 2.
  • a textilematerial comprising interlocked yarns of proteinaceous fibers modified by reaction with 1 to 20% by Weight of a water-insoluble linear addition copolymer of ethyl acrylate and 0.5 to 6% by weight of N-methylolacrylamide.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
US858028A 1959-07-27 1959-12-08 Process for shrink-proofing proteinaceous textile materials and the product therefrom Expired - Lifetime US3100674A (en)

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US858028A US3100674A (en) 1959-12-08 1959-12-08 Process for shrink-proofing proteinaceous textile materials and the product therefrom
GB35418/61A GB998188A (en) 1959-07-27 1960-07-26 Copolymers
GB4231260A GB968385A (en) 1959-12-08 1960-12-08 Protein containing textiles and stabilization thereof
FR846344A FR1275792A (fr) 1959-12-08 1960-12-08 Procédé de stabilisation de textiles renfermant des protéines

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3220086A (en) * 1962-04-14 1965-11-30 Foister Clay & Ward Ltd Process for treating wool for anti-felting purposes
US3372978A (en) * 1964-05-28 1968-03-12 Agriculture Usa Fibrous material carrying a deposit of a cross-linked polymer
US3630659A (en) * 1967-01-14 1971-12-28 Bayer Ag Process for preventing damage to natural protein-containing fibers
US4003865A (en) * 1973-02-02 1977-01-18 Troy Chemical Corporation Enzyme inhibitors, uses and compositions containing same
US4279959A (en) * 1977-11-03 1981-07-21 Rohm And Haas Company Water-insoluble copolymers containing amide-polyaldehyde thermosettable system
CN103668783A (zh) * 2013-12-10 2014-03-26 吴江市品信纺织科技有限公司 一种耐碱无纺布

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1054682A (fr) * 1963-04-13 1900-01-01
US4524093A (en) * 1984-04-30 1985-06-18 The B. F. Goodrich Company Fabric coating composition with low formaldehyde evolution

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2447540A (en) * 1945-05-18 1948-08-24 Montclair Res Corp Butadiene-acrylate interpolymer treatment of wool
US2447539A (en) * 1944-11-16 1948-08-24 Montclair Res Corp Treatment of wool
US2719072A (en) * 1953-04-10 1955-09-27 Rohm & Haas The stabilization of protein-containing textiles and the resulting products
US2780567A (en) * 1954-03-22 1957-02-05 Rohm & Haas Stabilization of protein-containing textiles
US2827359A (en) * 1954-03-22 1958-03-18 Rohm & Haas Process for stabilization of protein textiles with 4-vinyl pyridine copolymers and products produced therefrom
US2937920A (en) * 1957-04-23 1960-05-24 Varsenig Z Pasternak Nu-methylolacrylamide treatment of feathers

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2447539A (en) * 1944-11-16 1948-08-24 Montclair Res Corp Treatment of wool
US2447540A (en) * 1945-05-18 1948-08-24 Montclair Res Corp Butadiene-acrylate interpolymer treatment of wool
US2719072A (en) * 1953-04-10 1955-09-27 Rohm & Haas The stabilization of protein-containing textiles and the resulting products
US2780567A (en) * 1954-03-22 1957-02-05 Rohm & Haas Stabilization of protein-containing textiles
US2827359A (en) * 1954-03-22 1958-03-18 Rohm & Haas Process for stabilization of protein textiles with 4-vinyl pyridine copolymers and products produced therefrom
US2937920A (en) * 1957-04-23 1960-05-24 Varsenig Z Pasternak Nu-methylolacrylamide treatment of feathers

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3220086A (en) * 1962-04-14 1965-11-30 Foister Clay & Ward Ltd Process for treating wool for anti-felting purposes
US3372978A (en) * 1964-05-28 1968-03-12 Agriculture Usa Fibrous material carrying a deposit of a cross-linked polymer
US3630659A (en) * 1967-01-14 1971-12-28 Bayer Ag Process for preventing damage to natural protein-containing fibers
US4003865A (en) * 1973-02-02 1977-01-18 Troy Chemical Corporation Enzyme inhibitors, uses and compositions containing same
US4279959A (en) * 1977-11-03 1981-07-21 Rohm And Haas Company Water-insoluble copolymers containing amide-polyaldehyde thermosettable system
CN103668783A (zh) * 2013-12-10 2014-03-26 吴江市品信纺织科技有限公司 一种耐碱无纺布

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GB968385A (en) 1964-09-02
FR1275792A (fr) 1961-11-10

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