US3909195A - Process of modifying textile materials with polymerizable monomers - Google Patents

Process of modifying textile materials with polymerizable monomers Download PDF

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Publication number
US3909195A
US3909195A US242603A US24260362A US3909195A US 3909195 A US3909195 A US 3909195A US 242603 A US242603 A US 242603A US 24260362 A US24260362 A US 24260362A US 3909195 A US3909195 A US 3909195A
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United States
Prior art keywords
fibers
textile
liquid medium
textile fibers
cellulosic
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
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US242603A
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English (en)
Inventor
Greville Machell
Manuel A Thomas
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Deering Milliken Research Corp
Milliken Research Corp
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Milliken Research Corp
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Filing date
Publication date
Priority to NL301450D priority Critical patent/NL301450A/xx
Application filed by Milliken Research Corp filed Critical Milliken Research Corp
Priority to US242603A priority patent/US3909195A/en
Priority to ES293757A priority patent/ES293757A1/es
Priority to FR955147A priority patent/FR1375564A/fr
Priority to GB47717/63A priority patent/GB1067496A/en
Priority to LU44939D priority patent/LU44939A1/xx
Priority to BE640919A priority patent/BE640919A/xx
Priority to CH1495863D priority patent/CH1495863A4/xx
Priority to DE19631444049 priority patent/DE1444049A1/de
Priority to CH1495863A priority patent/CH485065A/xx
Application granted granted Critical
Publication of US3909195A publication Critical patent/US3909195A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • 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
    • 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
    • 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
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/18—Grafting textile fibers
    • 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
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/21—Nylon

Definitions

  • ABSTRACT A textile material is reacted with unsaturated, polymerizable compounds in the presence of a reaction catalyst in a process wherein the reactive material and the catalyst are contained in a liquid medium and the weight ratio between the liquid medium and the textile material is less than 25/ 1.
  • Ethylenically unsaturated compounds can be reacted with textile fibers, particularly keratin and cellulosic fibers, through a number of well-known processes, all of which may be utilized to conduct the process improvement of this invention.
  • these fibers may be reacted with the desired compound in the presence of a catalyst or initiator system for inducing polymerization of the compound.
  • a catalyst or initiator system for inducing polymerization of the compound.
  • azo catalysts such as azobisisobutyronitrile
  • the redox catalyst systemscomposed of a reducing agent and an oxidizing agent initiator are examples of a reducing agent and an oxidizing agent initiator.
  • the reducing agent may be an iron compound such as the ferrous salts, including ferrous sulfate, acetate,
  • phosphate ethylenediamine 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 sodium, potassium or ammonium thioglycollate
  • mercaptans such as hydrogen sulfide and sodium or potassium hydrosulfide
  • alkyl mercaptans such as butyl or ethyl mercaptans
  • mercaptan glycols such as beta-mercaptoethanol: alkanolamine sulfites, such as monoethanolamine sulfite and mono-isopropanol
  • 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) peroxide and di-(tert.-amyl) peroxide, such per- .oxides often being designated as ethyl, propyl, lauryl,
  • dialkyl peroxides e.g., diethyl peroxide, dipropyl peroxide, dilauryl peroxide, dioleyl peroxide, distearyl peroxide, di-(tert.- butyl) peroxide and di-
  • alkyl hydrogen peroxides e.g., tert.-butyl hydrogen peroxide (tert.-butyl hydroperoxide), tert.-amyl hydrogen peroxide (tert.-amyl hydroperoxide), etc.
  • symmetrical diacyl peroxides for instance peroxides which commonly are known under such names as acetyl peroxide, propionyl peroxide, lauroyl peroxide, stearoyl peroxide, malonyl peroxide, succinyl peroxide, phthaloyl peroxide, benzoyl peroxide, etc.
  • fatty oil acid peroxides e.g., coconut oil acid peroxides, etc.
  • unsymmetrical or mixed diacyl peroxides e.g., acetyl benzoyl peroxide, pro
  • organic peroxide initiators that can be employed are the following: tetralin hydroperoxide, tert.-butyl diperphthalate, cumene hydroperoxide, tert.-butyl perbenzoate, 2,4-dichlorobenzoyl peroxide, urea peroxide, caprylyl peroxide, pchlorobenzoyl peroxide, 2,2-bis(tert.-butyl peroxy) bu tane, hydroxyheptyl peroxide, diperoxide of benzaldehyde and the like.
  • oxidizing agents 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 may also be initiated by ceric ions, for example, in the form of ceric salts such as ceric nitrate, ceric sulfate, ceric ammonium nitrate, ceric ammonium sulfate, ceric ammonium pyrophosphatc, ceric iodate, and the like. This latter initiating system is preferred when the reaction is conducted on cellulosic fiber.
  • homopolymer that material which in some instances can be extracted from fibers treated by these techniques has been designated as homopolymer. It is realized, however, that some homopolymer may well be occluded or ionically bound within the interstices of the fibers and that not all of the polymeric material remaining on the substrate is covalently attached to the fibers, if indeed this is the reason the reacted material cannot be extracted from the fiber.
  • the term reacted polymer is intended to include both types of non-extractible polymer.
  • the process of this invention may be utilized to produce fibers containing extractible reacted compounds, although these products are generally less preferred.
  • N-dialkyl acrylamides for example: N,N'-dimethyl, -diethyl, -dipropyl, -dibutyl, -diamyl, -dihexyl, -dioctyl, etc., acrylamides; N-(panisyl) methacrylamide, N-(p-chlorophenyl) methacrylamide, N-phenyl methacrylamide, N-ethylmethylmethacrylamide, N-methylmethacrylamide, N-(ptolyl) methacrylamide and the like; the acrylic, alphaalkyl acrylic and alpha-haloacrylic esters of saturated monohydric alcohols, for instance saturated aliphatic monohydric alcohols, e.g., the methyl, ethyl, propyl, isopropyl, butyl, is
  • dichlorostyrene and the like the various cyanostyrenes, the various methoxystyrenes, e.g., pmethoxystyrene vinyl naphthalenes, e.g., 4-chloro-lvinylnaphthalene, 6chloro-2-vinylnaphthalene, etc.; vinyl and vinylidene halides, e.g., vinyl and vinylidene chlorides, bromides, etc.; alkyl vinyl ketones, e.g., methyl vinyl ketone, ethyl vinyl ketone, methyl isopropenyl ketone, etc.; itaconic and maleic diesters containing a single CH -$group,
  • the treatment of textile fibers in accordance with this'invention may be conducted at any desired temperature, although reactions in the presence of a redox catalyst system are preferably conducted at temperatures between about 40 and about 60C. A temperature in excess of about C is generally not preferred with this catalyst system since many of the components utilized in these systems degrade at elevated temperatures. In general, such conditions as concentrations of the reagents, pH, time and temperature may be modified to suit the individual circumstances and equipment utilized.
  • a swelling agent for the fibers in addition to the water normally used.
  • a swelling agent for the fibers, in addition to the water normally used.
  • a swelling agent for the fibers, in addition to the water normally used.
  • a swelling agent for example, for keratin fibers urea; thiourea; lithium salts, such as the chloride, bromide and iodide; guanadine compounds, such as the hydrochlorides; amides, such as formamide, N ,N- dimethyformamide, acetamide, N,N- dimethylacetamide and the like may be utilized.
  • swelling agents such as alkali-metal hydroxides, including sodium hydroxide and potassium hydroxide may be utilized.
  • Keratin fibers which may be treated in accordance with this invention include wool, mohair, alpaca, cashmere, vicuna, guanaco, camels hair, silk, llama and the like.
  • Cellulosic fibers which may be treated in accordance with this invention include natural cellulosic fibers, for example, cotton, paper, linen, jute, flex; regenerated cellulose fibers, for example, viscose rayon; fibers containing a limited number of acetyl groups, such as cellulose acetate; fibers which contain a limited number of methylether groups, such as partially methylated cellulose 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 containing at least about 85% combined acrylonitrile, such as acrylonitrile/methylacrylate (85/15').
  • polyamides such as poly(hexamethylene adipamide)
  • polyesters such as poly(ethylene terephthalate)
  • acrylic fibers such as acrylonitrile homopolymer or copolymers containing at least about 85% combined acrylonitrile, such as acrylonitrile/methylacrylate (85/15').
  • each wool sample is scoured by immersing in or passing therethrough an aqueous solution containing 0.5% on the weight of wool of Sulfonic N-95, a non-ionic surface active agent and 1.5% on the weight of wool of glacial acetic acid. After scouring for 20 minutes at F,
  • the sample is rinsed in water at 100F for l0l5 minutes.
  • Deionized water is used in preparing all aqueous media.
  • EXAMPLE 1 Into a 2-lb. Gaston County package dyeing machine are mounted 800 gms. of wool top, 400 gms. being mounted on each of 2 bobbins which are placed on the single perforated spindle of the dye machine. After scouring and rinsing, an aqueous solution made up from 7400 ccs of water, 1.74 gms. Fe(NO .9H O (0.03% Fe based on the wool weight), 12.2 ccs of a 50% solution of H 0 (50/1 molar ratio of peroxide based on Fe**), and 40 ccs of concentrated 1-1 80 is circulated through the machine and the wool top. After ten minutes, 960 gms.
  • Each system is then held at 7585F and forced back and forth through the fibers at a flow rate of about 35 gallons per minute for minutes, at a cycle of 3 minutes outside-in and 2 minutes inside-out.
  • outsidein is meant that the system is forced from the outside of the wook top package into the perforated spindle and through a recirculating system back to the outside of the wool top package. In the inside out flow pattern, this procedure is reversed.
  • the temperature is then increased at 120F and the reaction is continued at this temperature for an addi tional 105 minutes.
  • the wool top is removed from the machine and found to have increased in weight by the levels shown in Table I.
  • a novel process for reacting textile fibers with ethylenically unsaturated compounds comprising:
  • the weight ratio of the liquid medium to the textile fibers being between about 8/1 and about 20/1;
  • said textile fibers comprising keratinic fibers, cellulosic fibers or blends of either keratinic or cellulosic fibers with acrylic fibers, synthetic polyamide fibers or synthetic polyester fibers.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Zoology (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
US242603A 1962-12-06 1962-12-06 Process of modifying textile materials with polymerizable monomers Expired - Lifetime US3909195A (en)

Priority Applications (10)

Application Number Priority Date Filing Date Title
NL301450D NL301450A (enrdf_load_stackoverflow) 1962-12-06
US242603A US3909195A (en) 1962-12-06 1962-12-06 Process of modifying textile materials with polymerizable monomers
ES293757A ES293757A1 (es) 1962-12-06 1963-11-22 Procedimiento de hacer reaccionar compuestos etilénicamente no saturados con fibras textiles en un medio líquido
FR955147A FR1375564A (fr) 1962-12-06 1963-11-27 Procédé de traitement de fibres textiles
GB47717/63A GB1067496A (en) 1962-12-06 1963-12-03 The treatment of textile fibres
LU44939D LU44939A1 (enrdf_load_stackoverflow) 1962-12-06 1963-12-04
BE640919A BE640919A (enrdf_load_stackoverflow) 1962-12-06 1963-12-06
CH1495863D CH1495863A4 (enrdf_load_stackoverflow) 1962-12-06 1963-12-06
DE19631444049 DE1444049A1 (de) 1962-12-06 1963-12-06 Verfahren zur Umsetzung von Textilfasern mit aethylenisch ungesaettigten Verbindungen
CH1495863A CH485065A (fr) 1962-12-06 1963-12-06 Procede pour faire reagir un compose ethylenique avec des fibres textiles de keratine

Applications Claiming Priority (1)

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US242603A US3909195A (en) 1962-12-06 1962-12-06 Process of modifying textile materials with polymerizable monomers

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US3909195A true US3909195A (en) 1975-09-30

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US (1) US3909195A (enrdf_load_stackoverflow)
BE (1) BE640919A (enrdf_load_stackoverflow)
CH (2) CH1495863A4 (enrdf_load_stackoverflow)
DE (1) DE1444049A1 (enrdf_load_stackoverflow)
ES (1) ES293757A1 (enrdf_load_stackoverflow)
GB (1) GB1067496A (enrdf_load_stackoverflow)
LU (1) LU44939A1 (enrdf_load_stackoverflow)
NL (1) NL301450A (enrdf_load_stackoverflow)

Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4065256A (en) * 1975-01-31 1977-12-27 Toyo Boseki Kabushiki Kaisha Method for graft polymerization of shaped article of hydrophobic synthetic polymer
US4090844A (en) * 1977-06-23 1978-05-23 The United States Of America As Represented By The Secretary Of Agriculture Process of producing high performance durable-press cotton
US4135877A (en) * 1977-06-06 1979-01-23 Kanebo, Ltd. Process for improving antistatic and hygroscopic properties of fibers or fibrous structures made thereof
US4369036A (en) * 1980-12-04 1983-01-18 Toray Industries, Inc. Method of modifying synthetic or natural polyamide products
US4410694A (en) * 1981-03-18 1983-10-18 Kao Soap Co., Ltd. Process for producing fibrous carboxymethyl cellulose
US4521450A (en) * 1982-06-22 1985-06-04 Asea Aktiebolag Method of increasing the electrical conductivity of cellulose-based materials or other impregnable materials
US4631066A (en) * 1983-07-26 1986-12-23 Teijin Limited Method for improving light-resistance of aromatic polyamide fibers
US4743267A (en) * 1982-06-21 1988-05-10 International Yarn Corporation Of Tennessee Process for improving polymer fiber properties and fibers produced thereby
US4803096A (en) * 1987-08-03 1989-02-07 Milliken Research Corporation Electrically conductive textile materials and method for making same
US4877646A (en) * 1988-06-27 1989-10-31 Milliken Research Corporation Method for making electrically conductive textile materials
US5230711A (en) * 1991-04-15 1993-07-27 Cassella Ag Dyeing of cellulose with soluble sulphur dyes without reducing agent
US5292573A (en) * 1989-12-08 1994-03-08 Milliken Research Corporation Method for generating a conductive fabric and associated product
US5614591A (en) * 1994-12-15 1997-03-25 The Virkler Company Process and composition for imparting durable press properties to textile fabrics
US20100028279A1 (en) * 2008-07-31 2010-02-04 Jose Antonio Carballada Method and Composition for Maintaining Hair Dye Color
US20100120871A1 (en) * 2008-11-10 2010-05-13 Dawson Jr Thomas Larry Hair care compositions, methods, and articles of commerce that can increase the appearance of thicker and fuller hair
US20120241680A1 (en) * 2009-07-24 2012-09-27 The Board Of Trustees Of The University Of Alabama Conductive composites prepared using ionic liquids
US9358197B2 (en) 2012-06-15 2016-06-07 The Procter & Gamble Company Method employing polyols when chemically modifying the internal region of a hair shaft
US9986809B2 (en) 2013-06-28 2018-06-05 The Procter & Gamble Company Aerosol hairspray product comprising a spraying device
US10024841B2 (en) 2014-08-29 2018-07-17 The Procter & Gamble Company Device for testing the properties of fibres
US10131488B2 (en) 2015-06-01 2018-11-20 The Procter And Gamble Company Aerosol hairspray product comprising a spraying device
US11311749B2 (en) 2011-09-15 2022-04-26 The Procter And Gamble Company Aerosol hairspray for styling and/or shaping hair
US12128118B2 (en) 2021-07-29 2024-10-29 The Procter & Gamble Company Aerosol dispenser containing a hairspray composition and a nitrogen propellant

Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2732317A (en) * 1956-01-24 Modified cellulose and method of
US2764504A (en) * 1952-08-28 1956-09-25 Du Pont Coating process and products therefrom
US2784052A (en) * 1954-04-23 1957-03-05 Du Pont Process of preparing waterproof films, fabrics, filaments, and yarns of regenerated cellulose containing within a waterproof addition polymer and products produced therefrom
US2956899A (en) * 1956-10-18 1960-10-18 Du Pont Process of forming graft polymers on a shaped polymeric organic substrate
US3046078A (en) * 1958-03-18 1962-07-24 American Cyanamid Co Graft polymerization process
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
US3115418A (en) * 1955-04-29 1963-12-24 Centre Nat Rech Scient Process of producing graft polymers and resultant graft polymer
US3218117A (en) * 1961-08-02 1965-11-16 American Cyanamid Co Polypropylene fibers and method for preparing same
US3236584A (en) * 1960-03-23 1966-02-22 Edward F Degering Graft polymerization on a paper base by ionizing radiation
US3291560A (en) * 1962-12-10 1966-12-13 Deering Milliken Res Corp Method of forming polymers on fibrous substrates through high velocity impingement with solutions containing unsaturated monomers and chemical catalysts
US3514385A (en) * 1966-07-19 1970-05-26 Du Pont Process for radiation grafting onto a partially swollen cellulosic substrate

Patent Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2732317A (en) * 1956-01-24 Modified cellulose and method of
US2764504A (en) * 1952-08-28 1956-09-25 Du Pont Coating process and products therefrom
US2784052A (en) * 1954-04-23 1957-03-05 Du Pont Process of preparing waterproof films, fabrics, filaments, and yarns of regenerated cellulose containing within a waterproof addition polymer and products produced therefrom
US3115418A (en) * 1955-04-29 1963-12-24 Centre Nat Rech Scient Process of producing graft polymers and resultant graft 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
US3046078A (en) * 1958-03-18 1962-07-24 American Cyanamid Co Graft polymerization process
US3236584A (en) * 1960-03-23 1966-02-22 Edward F Degering Graft polymerization on a paper base by ionizing radiation
US3218117A (en) * 1961-08-02 1965-11-16 American Cyanamid Co Polypropylene fibers and method for preparing same
US3291560A (en) * 1962-12-10 1966-12-13 Deering Milliken Res Corp Method of forming polymers on fibrous substrates through high velocity impingement with solutions containing unsaturated monomers and chemical catalysts
US3514385A (en) * 1966-07-19 1970-05-26 Du Pont Process for radiation grafting onto a partially swollen cellulosic substrate

Cited By (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4065256A (en) * 1975-01-31 1977-12-27 Toyo Boseki Kabushiki Kaisha Method for graft polymerization of shaped article of hydrophobic synthetic polymer
US4135877A (en) * 1977-06-06 1979-01-23 Kanebo, Ltd. Process for improving antistatic and hygroscopic properties of fibers or fibrous structures made thereof
US4090844A (en) * 1977-06-23 1978-05-23 The United States Of America As Represented By The Secretary Of Agriculture Process of producing high performance durable-press cotton
US4369036A (en) * 1980-12-04 1983-01-18 Toray Industries, Inc. Method of modifying synthetic or natural polyamide products
US4410694A (en) * 1981-03-18 1983-10-18 Kao Soap Co., Ltd. Process for producing fibrous carboxymethyl cellulose
US4743267A (en) * 1982-06-21 1988-05-10 International Yarn Corporation Of Tennessee Process for improving polymer fiber properties and fibers produced thereby
US4521450A (en) * 1982-06-22 1985-06-04 Asea Aktiebolag Method of increasing the electrical conductivity of cellulose-based materials or other impregnable materials
US4631066A (en) * 1983-07-26 1986-12-23 Teijin Limited Method for improving light-resistance of aromatic polyamide fibers
US4803096A (en) * 1987-08-03 1989-02-07 Milliken Research Corporation Electrically conductive textile materials and method for making same
US4877646A (en) * 1988-06-27 1989-10-31 Milliken Research Corporation Method for making electrically conductive textile materials
US5292573A (en) * 1989-12-08 1994-03-08 Milliken Research Corporation Method for generating a conductive fabric and associated product
US5230711A (en) * 1991-04-15 1993-07-27 Cassella Ag Dyeing of cellulose with soluble sulphur dyes without reducing agent
US5614591A (en) * 1994-12-15 1997-03-25 The Virkler Company Process and composition for imparting durable press properties to textile fabrics
US20100028279A1 (en) * 2008-07-31 2010-02-04 Jose Antonio Carballada Method and Composition for Maintaining Hair Dye Color
US7981167B2 (en) 2008-07-31 2011-07-19 The Procter & Gamble Company Method and composition for maintaining hair dye color
US20100120871A1 (en) * 2008-11-10 2010-05-13 Dawson Jr Thomas Larry Hair care compositions, methods, and articles of commerce that can increase the appearance of thicker and fuller hair
US20120241680A1 (en) * 2009-07-24 2012-09-27 The Board Of Trustees Of The University Of Alabama Conductive composites prepared using ionic liquids
US8784691B2 (en) * 2009-07-24 2014-07-22 Board Of Trustees Of The University Of Alabama Conductive composites prepared using ionic liquids
US11311749B2 (en) 2011-09-15 2022-04-26 The Procter And Gamble Company Aerosol hairspray for styling and/or shaping hair
US9358197B2 (en) 2012-06-15 2016-06-07 The Procter & Gamble Company Method employing polyols when chemically modifying the internal region of a hair shaft
US9986809B2 (en) 2013-06-28 2018-06-05 The Procter & Gamble Company Aerosol hairspray product comprising a spraying device
US10024841B2 (en) 2014-08-29 2018-07-17 The Procter & Gamble Company Device for testing the properties of fibres
US10131488B2 (en) 2015-06-01 2018-11-20 The Procter And Gamble Company Aerosol hairspray product comprising a spraying device
US12128118B2 (en) 2021-07-29 2024-10-29 The Procter & Gamble Company Aerosol dispenser containing a hairspray composition and a nitrogen propellant

Also Published As

Publication number Publication date
GB1067496A (en) 1967-05-03
DE1444049A1 (de) 1969-02-06
BE640919A (enrdf_load_stackoverflow) 1964-04-01
CH485065A (fr) 1970-01-31
NL301450A (enrdf_load_stackoverflow)
ES293757A1 (es) 1964-04-16
CH1495863A4 (enrdf_load_stackoverflow) 1969-10-15
LU44939A1 (enrdf_load_stackoverflow) 1964-02-04

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