US3437420A - Keratin fibers modified with combination of hard polymer forming and soft polymer forming monomers to improve quality of knitted goods made therewith - Google Patents

Keratin fibers modified with combination of hard polymer forming and soft polymer forming monomers to improve quality of knitted goods made therewith Download PDF

Info

Publication number
US3437420A
US3437420A US242639A US3437420DA US3437420A US 3437420 A US3437420 A US 3437420A US 242639 A US242639 A US 242639A US 3437420D A US3437420D A US 3437420DA US 3437420 A US3437420 A US 3437420A
Authority
US
United States
Prior art keywords
polymer forming
keratin fibers
fibers
peroxide
ethylenically unsaturated
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
US242639A
Other languages
English (en)
Inventor
Edgar Dare Bolinger
Greville Machell
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.)
Deering Milliken Research Corp
Milliken Research Corp
Original Assignee
Milliken Research Corp
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
Application filed by Milliken Research Corp filed Critical Milliken Research Corp
Application granted granted Critical
Publication of US3437420A publication Critical patent/US3437420A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

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
    • D06M11/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising
    • D06M11/01—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with hydrogen, water or heavy water; with hydrides of metals or complexes thereof; with boranes, diboranes, silanes, disilanes, phosphines, diphosphines, stibines, distibines, arsines, or diarsines or complexes thereof
    • D06M11/05—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with hydrogen, water or heavy water; with hydrides of metals or complexes thereof; with boranes, diboranes, silanes, disilanes, phosphines, diphosphines, stibines, distibines, arsines, or diarsines or complexes thereof with water, e.g. steam; with heavy water
    • 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
    • D06M14/00—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials
    • D06M14/02—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials on to materials of natural origin
    • D06M14/06—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials on to materials of natural origin of animal origin, e.g. wool or silk
    • 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
    • D06M14/00—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials
    • D06M14/18—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials using wave energy or particle radiation
    • D06M14/20—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials using wave energy or particle radiation on to materials of natural origin
    • D06M14/24—Graft polymerisation of monomers containing carbon-to-carbon unsaturated bonds on to fibres, threads, yarns, fabrics, or fibrous goods made from such materials using wave energy or particle radiation on to materials of natural origin of animal origin, e.g. wool or silk
    • 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

Definitions

  • This invention relates to a process for improving the flat stability of fabrics containing keratin fibers and to the fabrics so produced.
  • This difliculty can be overcome in accordance with this invention by preparing the desired fabric from keratin fibers which have been reacted with a particular class of ethylenically unsaturated compounds.
  • Wool fabrics have been reacted with a wide variety of ethylenically unsaturated compounds, generally to impart to such fabrics a resistance to felting shrinkage effects or for experimental purposes merely to ascertain the effects on the fibers of reaction with various ethylenically unsaturated compounds.
  • ethylenically unsaturated compounds utilized herein could be reacted with keratin fibers to provide a high degree of flat stability in fabrics produced therefrom.
  • flat stability as utilized herein is meant the property whereby a fabric tends to lie flat rather than curl up at the edges, even when cut, while lying in a flat state.
  • the class of ethylenically unsaturated compounds suitable for use in accordance with this invention includes those compounds which in polymer form, have a glass transition temperature less than about 40 C., preferably below about 0 C.
  • the glass transition temperature is a well-known property and is the temperature at which a sheet of a polymer is transformed from a glass-like solid state to a softened state. Above the glass transition temperature, the volume of the sheet increases more rapidly with an increase in temperature. The point at which this volume increase begins may be readily determined in a plot of volume versus temperature. These glass transition temperatures may be readily determined by standard A.S.T.M. heat deflection temperature measurements, e.g., A.S.T.M. Designation D648-45T, issued 1941, revised 1944, 1945.
  • acrylic acid esters of unsaturated aliphatic monohydric alcohols for example, methyl, ethyl, a-chloroethyl, propyl, isopropyl, butyl, isobutyl, amyl, isoamyl, hexyl, heptyl, octyl, 2-ethyl hexyl, nonyl, decyl, and the like and methacrylates containing more than two carbon atoms in the ester grouping.
  • An optimum balance of reactivity and improved properties is found in those esters containing from 4 to 8 carbon atoms in the ester grouping,
  • acids e.g., vinyl propionates, valerates, laurates, etc; vinyl pyridine, vinyl pyriole and the like, as well as hydroxyalkyl esters of acrylic and methacrylic acid, such as hydroxyethyl acrylate, hydroxymethyl acrylate, t-butylaminoethyl methacrylate and the like.
  • ethylenically unsaturated compounds having glass transition temperatures in excess of about 40 C., particularly in excess of about C. generally do not provide the desired improvement in flat stability
  • such compounds may be blended with ethylenically unsaturated compounds having glass transition temperatures below about 40 C. to provide such improvement, provided the latter class of compound is present in at least a major proportion.
  • fibers treated in accordance with this invention retain crease angles after immersion in water to a degree comparable to untreated wool, so that fabrics having essentially the same creasability as untreated fabrics, with greatly improved flat stability, may be produced in accordance with this invention. Furthermore, by treating loose fibers in accordance with a preferred embodiment of this invention, feltable fabrics of superior hand and physical properties are obtained.
  • This improved flat stability enhances the manufacture of garments from both woven and knitted fabrics, particularly the latter. Furthermore, the heavy rib conventionally knitted along the edge of knitted fabrics to prevent curling may be greatly reduced in size or eliminated where unravelling can be otherwise avoided.
  • Ethylenically unsaturated compounds may be reacted wit-h keratin fibers through a number of well-known processes.
  • keratin fibers may be reacted with the desired compounds in the presence of a catalyst or initiator system for inducing polymerization of the compounds.
  • a catalyst or initiator system for inducing polymerization of the compounds.
  • azo catalysts such as azobisisobutyronitrile
  • irradiation under the influence of high energy fields including the diverse actinic radiations, such as ultra violet X-ray and gamma radiation as well as radiations from radioactive materials such as cobalt-60.
  • the reaction of keratin fibers with ethylenically unsaturated compounds be conducted in the presence of a redox catalyst system, Le. a catalyst system composed of a reducing agent and an oxidizing agent initiator.
  • a redox catalyst system composed of a reducing agent and an oxidizing agent initiator.
  • the reducing agent may be an iron compounds, such as the ferrous salts including ferrous sulfate, acetate, phosphate, ct-hylenediamine tetra-acetate; metallic formaldehyde sulfoxylates, such as zinc formaldehyde sulfoxylate; alkali-metal sulfoxylates, such as sodium formaldehyde sulfoxylate; alkali-metal sulfites, such as sodium and-potassium bisulfite, sulfite, metabisulfite or hydrosulfite; mercaptan acids, such as thioglycollic acid and its water-soluble salts, such as sodium, potassium or ammonium thioglycollate; mercaptans, such as hydrogen sulfide and sodium or potassium hydrosulfide; alkyl mercaptans, such as butyl or ethyl mercaptans and mercaptan glycols,
  • a salt of hydrazine may be used as the reducing agent, the acid moiety of the salt being derived from any acid, such as hydrochloric, hydrobromic, sulfuric, sulfurous, phosphoric, benzoic, acetic and the like.
  • Suitable oxidizing agent initiators for use in the redox catalyst system include inorganic peroxides, e.g., hydrogen peroxide, barium peroxide, magnesium peroxide, etc., and the various organic peroxy catalysts, illustrative examples of which are the dialkyl peroxides, e.g., diethyl peroxide, dipropyl peroxide, dilauryl peroxide, dioleyl peroxide, distearyl peroxide, di-(tert.-butyl)peroxi-de and di-(tert.-amyl)peroxide, such peroxides often being designated as ethyl, propyl, lauryl, oleyl, stearyl, tert.-butyl and tert.-amyl peroxides; the alkyl hydrogen peroxides, e.g., tert.-butyl hydrogen peroxide (tert.-butyl hydroperoxide), ter
  • organic peroxide initiators that can be employed are the following: tetralin hydroperoxide, tert.-butyl diperphthalate, cumene hydroperoxi-de, tert.- butyl perbenzoate, 2,4-dichlorobenzoyl peroxide, urea peroxide, caprylyl peroxide, p-chlorobenzoyl peroxide, 2,2-bis(tert.-butyl peroxy) butane, hydroxyheptyl peroxide, and the diperoxide of benzaldehyde.
  • oxidizing agent initiators particularly the salts of inorganic peracids
  • Ferric salts can be used as oxidizing agents and form a redox catalyst system with hydrogen peroxide, in which case the peroxide functions as a reducing agent.
  • the reaction between keratin fibers and ethylenically unsaturated compounds most readily takes place in the presence of water. This generally presents no problem since only small amounts are necessary for this improvement and since the catalyst components and/ or monomers are generally applied to the fibers in an aqueous medium. If the substrate is dry at the time of treatment, the reaction rate will be slower. Consequently, it is preferred that the substrate be wet with water when the reaction takes place. Ionic or non-ionic surface active agents may be utilized in any aqueous medium used in applying the reagents.
  • the reaction of the above monomers or their derivatives with keratin fibers may be conducted at room temperature, although temperatures between about 40 and 60 C. are generally preferred. A temperature in excess of about 100 C. is generally not preferred, since undue degradation of some of the components of the preferred catalyst system, the redox system, occurs at this elevated temperature. In general, such conditions as concentrations of the reagents, pH, time and temperature of reaction may be modified to suit the individual circumstances, while still providing the desired degree of reaction.
  • the fibrous substrate may be exposed to the monomer in vapor, liquid or emulsion form. Exposure to the vapors of the monomers is conveniently carried out by entraining the vapor in an oxygen free gas, such as nitrogen, and then interposing the substrate in a stream of the gas and vapor. Inert volatile liquids, such as water or an alcohol, may be mixed with the compound being vaporized. Similarly, the fibrous substrate may be immersed in a liquid system, either solution or emulsion type, containing the desired amount of monomer.
  • Any desired apparatus may be used to apply one or more of the above class of ethylenically unsaturated COlTlpounds to keratin fibers, such as by padding, spraying or the like, but preferred apparatus includes forced-flow equipment, such as disclosed in the copending application Ser. No. 243,671, now Patent 3,291,560. With this apparatus, the desired systems can be repeatedly forced back and forth through keratin fibers at controllable flow rates to provide particularly good reaction results.
  • While the process of this invention is particularly adapted to fibrous substrates composed essentially of keratin fibers, particularly those composed entirely of wool fibers, it is also applicable to substrates wherein synthetic or natural fibers are blended with keratin fibers and to blends with other keratin fibers, such as mohair, alpaca, cashmere, vicuna, guanaco, camel's hair, silk, llama and the like.
  • the preferred synthetic fibers include polyamides, such as poly(hexamethylene adipamide); polyesters, such as poly(ethylene terephthalate); and acrylic fibers, such as acrylonitrile homopolymer or copolymers of acrylonitrile containing at least about 85% combined acrylonitrile, such as acrylonitrile/ methyl acrylate (85/ 15) and cellulosics, such as cellulose acetate and viscose rayon.
  • polyamides such as poly(hexamethylene adipamide)
  • polyesters such as poly(ethylene terephthalate)
  • acrylic fibers such as acrylonitrile homopolymer or copolymers of acrylonitrile containing at least about 85% combined acrylonitrile, such as acrylonitrile/ methyl acrylate (85/ 15) and cellulosics, such as cellulose acetate and viscose rayon.
  • cotton is preferred.
  • the keratin fibers treated in accordance with this invention
  • keratin fibers In order to provide acceptable fabric aesthetic and physical properties, it is preferred to conduct the desired reaction on keratin fibers in relatively loose form, i.e., prior to processing into yarn as in top, tow, roving, sliver and the like. Fabrics produced from these fibers through conventional processing techniques are characterized by softer handle, better draperability and tear strength, among other improvements, even though more ethylenically unsaturated compound is present in the fabric than is possible when a fabric per se is treated. Similar improvement in fiat stability is obtained when yarns are treated and processed into fabric, but other aesthetic properties, such as handle, will be diminished by this less preferred technique.
  • Example I Onto the beam of a lO0-lb. capacity Gaston County package dye machine are wound 63 lbs. of wool top. The beam is then mounted over the perforated spindle, the machine is closed, and the wool is scoured for 30 minutes at 140 F. with 80 gallons of water containing 149 gms. of Synfac-905, a non-ionic wetting agent containing a nonylphenol-ethylene oxide (1/9 to l/2 molar ratio) condensation product and 429 gms. of acetic acid. During the scouring operation, as in all succeeding operations in this example, the liquids are forced back and forth through the wool at a cycle for 4 minutes outside to inside, 6 minutes inside to outside.
  • a redox catalyst system maintained at 100 F. and composed of 63 gms. of Fe(NO 429 gms. of 50% H and 75 gallons of water, adjusted to a pH of 1.35 with 12 lbs. of H 80 is passed through the wool for '20 minutes. The flow rate of the system through the wool is measured at about 120 gallons per minute.
  • the wool top treated in this manner is found to have increased in weight by 75%. After boiling in acetone for one hour the wool top is found to weight approximately the same.
  • a 4-inch length of the top treated in this manner weighing about 19 milligrams is mounted as a tight loop with a -mil. diameter piano wire.
  • the loop is then pressed at about 100 lbs. per square inch at 300 F. for 3 minutes in a hydraulic press.
  • the pressed loop is then placed in water, heated to 120 F. for 20 minutes, dried, and the angle formed by the creased top is measured at 141, as compared to an angle of 162 for a similar length of untreated wool top.
  • the fibers so treated are processed into yarn which is then knitted into a jersey-type fabric.
  • This fabric lies flat without curling at the edges while laying on a flat table.
  • the fabric is then cut lengthwise with a pair of straightedge scissors to the entire length of the fabric.
  • the cut edge remains flat on the table.
  • this latter procedure is conducted on a similar knitted fabric but composed of untreated wool fiber, the cut edge curls to a great extent towards the center of the fabric.
  • a woven fabric similarly remains flat after cutting.
  • This fabric is also immersed in water at 140 F. for one hour and is found to shrink in area by grater than 25%, indicating it could be felted if desired.
  • Example II Similar results are obtained when a fabric is produced from fibers having reacted therewith ethyl acrylate to 90% pickup (154 retained crease angle), ethyl acrylate to a pickup of 117% (retained crease angle of 147), methylmethacrylate and butyl acrylate in equimolar ratios to a pickup of 68% (retained crease angle of 112),
  • a process of producing fabrics having improved properties comprising reacting with keratin fibers at least one ethylenically unsaturated compound having, in polymer form, a glass transition temperature less than about 40 C. and with at least one ethylenically unsaturated compound having, in polymer form, a glass transition temperature greater than about 50 C., the compound having the lower glass transition temperature being present in at least a major proportion, the total weight increase in said fibers being greater than about 50%; and knitting a fabric containing said fibers in at least a major proportion, said fabric being characterized by a high degree of fiat stability and feltability.
  • the ethylenically unsaturated compound comprises an acrylic acid ester of a saturated aliphatic monohydric alcohol.

Landscapes

  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Zoology (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Toxicology (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
US242639A 1962-12-06 1962-12-06 Keratin fibers modified with combination of hard polymer forming and soft polymer forming monomers to improve quality of knitted goods made therewith Expired - Lifetime US3437420A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US24263962A 1962-12-06 1962-12-06

Publications (1)

Publication Number Publication Date
US3437420A true US3437420A (en) 1969-04-08

Family

ID=22915601

Family Applications (1)

Application Number Title Priority Date Filing Date
US242639A Expired - Lifetime US3437420A (en) 1962-12-06 1962-12-06 Keratin fibers modified with combination of hard polymer forming and soft polymer forming monomers to improve quality of knitted goods made therewith

Country Status (4)

Country Link
US (1) US3437420A (enrdf_load_stackoverflow)
BE (1) BE640926A (enrdf_load_stackoverflow)
GB (1) GB1067497A (enrdf_load_stackoverflow)
LU (1) LU44962A1 (enrdf_load_stackoverflow)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3633591A (en) * 1969-05-29 1972-01-11 Colgate Palmolive Co Treatment of keratinous substrates with a reducing agent and thereafter an oxidizing solution of a vinyl monomer
US3634022A (en) * 1969-05-29 1972-01-11 Colgate Palmolive Co Form-setting keratin substrates by a chemical treatment involving a vinyl monomer
US20080066773A1 (en) * 2006-04-21 2008-03-20 Anderson Daniel G In situ polymerization for hair treatment

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2406412A (en) * 1942-08-21 1946-08-27 Ici Ltd Treatment of wool fibers
US2940869A (en) * 1956-07-12 1960-06-14 Du Pont Process of adhering an organic compound to a shaped organic polymer
US2956899A (en) * 1956-10-18 1960-10-18 Du Pont Process of forming graft polymers on a shaped polymeric organic substrate
US3005730A (en) * 1954-10-25 1961-10-24 Jr Clay E Pardo Shrinkproofing of wool with n, n'-methylene bis-acrylamide polymerized in situ and the modified wool
US3008920A (en) * 1959-04-27 1961-11-14 Dow Chemical Co Method of inhibiting homopolymerization in graft copolymers with copper salts
US3031334A (en) * 1954-11-05 1962-04-24 Harold P Lundgren Process for shrinkproofing fibers with vinyl derivatives
US3083118A (en) * 1958-03-04 1963-03-26 Tee Pak Inc Method of depositing a polymer of olefinically unsaturated monomer within a polymeric material and the resulting product

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2406412A (en) * 1942-08-21 1946-08-27 Ici Ltd Treatment of wool fibers
US3005730A (en) * 1954-10-25 1961-10-24 Jr Clay E Pardo Shrinkproofing of wool with n, n'-methylene bis-acrylamide polymerized in situ and the modified wool
US3031334A (en) * 1954-11-05 1962-04-24 Harold P Lundgren Process for shrinkproofing fibers with vinyl derivatives
US2940869A (en) * 1956-07-12 1960-06-14 Du Pont Process of adhering an organic compound to a shaped organic polymer
US2956899A (en) * 1956-10-18 1960-10-18 Du Pont Process of forming graft polymers on a shaped polymeric organic substrate
US3083118A (en) * 1958-03-04 1963-03-26 Tee Pak Inc Method of depositing a polymer of olefinically unsaturated monomer within a polymeric material and the resulting product
US3008920A (en) * 1959-04-27 1961-11-14 Dow Chemical Co Method of inhibiting homopolymerization in graft copolymers with copper salts

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3633591A (en) * 1969-05-29 1972-01-11 Colgate Palmolive Co Treatment of keratinous substrates with a reducing agent and thereafter an oxidizing solution of a vinyl monomer
US3634022A (en) * 1969-05-29 1972-01-11 Colgate Palmolive Co Form-setting keratin substrates by a chemical treatment involving a vinyl monomer
US3676550A (en) * 1969-05-29 1972-07-11 Colgate Palmolive Co Modification of reduced keratinous substrates with a vinyl monomer
US20080066773A1 (en) * 2006-04-21 2008-03-20 Anderson Daniel G In situ polymerization for hair treatment

Also Published As

Publication number Publication date
LU44962A1 (enrdf_load_stackoverflow) 1964-02-06
GB1067497A (en) 1967-05-03
BE640926A (enrdf_load_stackoverflow) 1964-04-01

Similar Documents

Publication Publication Date Title
US3995998A (en) Method of polymerizing and fixing carboxyl-containing vinyl monomers in high conversion on fibrous substrates
US3909195A (en) Process of modifying textile materials with polymerizable monomers
US2406454A (en) Treatment of paper or textile fabrics
US3220869A (en) Process for improving textile fabrics
US3395970A (en) Method of carbonizing polyacrylonitrile impregnated cellulose, cyanoethylated cellulose and acrylonitrile graft copolymerized cellulose textiles
US2985501A (en) Process of producing flat drying, wet crease resistant cellulosic fabrics by reaction with cross-linking agents and products produced thereby
US3933122A (en) Vapor deposition apparatus
US3125405A (en) Method of crease-proofing cellulosic
US2406453A (en) Treatment of paper or textile fabrics
US3475114A (en) Modification of keratin fibers with ethylenically unsaturated compounds in the presence of aqueous solutions of fiber swelling agents
US3437420A (en) Keratin fibers modified with combination of hard polymer forming and soft polymer forming monomers to improve quality of knitted goods made therewith
US2988417A (en) Process for crease-proofing cellulosic fabrics
US2499653A (en) Treatment of protein-containing textile materials and products thereof
US3246946A (en) Method of crease-proofing cellulosic fabrics and fabrics obtained
US3291560A (en) Method of forming polymers on fibrous substrates through high velocity impingement with solutions containing unsaturated monomers and chemical catalysts
US2565259A (en) Treatment of protein-containing textile materials and products thereof
US3510247A (en) Modification of cellulosic materials with tertiary bis-acrylamides
US3583855A (en) Modification of keratinic fibers with ethylenically unsaturated compounds
US3799738A (en) Flame retardant process for cellulosics
US3634021A (en) Modification of cellulosic fibers with ethylenically unsaturated compounds
US3100674A (en) Process for shrink-proofing proteinaceous textile materials and the product therefrom
WO1992008835A1 (en) Improvements in or relating to non-woven fibrous materials
US3457027A (en) Improving the crimpability of keratinous fibers by reacting same with a vinyl aromatic compound in combination with an acrylic ester
US3708261A (en) Compounds having methylol groups and unsaturated groups are used with selected catalysts to produce a durable press product
US3794465A (en) Finishes for textile fabrics