US3909195A - Process of modifying textile materials with polymerizable monomers - Google Patents
Process of modifying textile materials with polymerizable monomers Download PDFInfo
- 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
- Authority
- US
- 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
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
-
- 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.
Landscapes
- 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)
Priority Applications (10)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NL301450D NL301450A (xx) | 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 (xx) | 1962-12-06 | 1963-12-04 | |
BE640919A BE640919A (xx) | 1962-12-06 | 1963-12-06 | |
CH1495863D CH1495863A4 (xx) | 1962-12-06 | 1963-12-06 | |
CH1495863A CH485065A (fr) | 1962-12-06 | 1963-12-06 | Procede pour faire reagir un compose ethylenique avec des fibres textiles de keratine |
DE19631444049 DE1444049A1 (de) | 1962-12-06 | 1963-12-06 | Verfahren zur Umsetzung von Textilfasern mit aethylenisch ungesaettigten Verbindungen |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US242603A US3909195A (en) | 1962-12-06 | 1962-12-06 | Process of modifying textile materials with polymerizable monomers |
Publications (1)
Publication Number | Publication Date |
---|---|
US3909195A true US3909195A (en) | 1975-09-30 |
Family
ID=22915457
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US242603A Expired - Lifetime US3909195A (en) | 1962-12-06 | 1962-12-06 | Process of modifying textile materials with polymerizable monomers |
Country Status (8)
Country | Link |
---|---|
US (1) | US3909195A (xx) |
BE (1) | BE640919A (xx) |
CH (2) | CH485065A (xx) |
DE (1) | DE1444049A1 (xx) |
ES (1) | ES293757A1 (xx) |
GB (1) | GB1067496A (xx) |
LU (1) | LU44939A1 (xx) |
NL (1) | NL301450A (xx) |
Cited By (22)
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)
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 |
-
0
- NL NL301450D patent/NL301450A/xx unknown
-
1962
- 1962-12-06 US US242603A patent/US3909195A/en not_active Expired - Lifetime
-
1963
- 1963-11-22 ES ES293757A patent/ES293757A1/es not_active Expired
- 1963-12-03 GB GB47717/63A patent/GB1067496A/en not_active Expired
- 1963-12-04 LU LU44939D patent/LU44939A1/xx unknown
- 1963-12-06 DE DE19631444049 patent/DE1444049A1/de active Pending
- 1963-12-06 CH CH1495863A patent/CH485065A/xx not_active IP Right Cessation
- 1963-12-06 CH CH1495863D patent/CH1495863A4/xx unknown
- 1963-12-06 BE BE640919A patent/BE640919A/xx unknown
Patent Citations (11)
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)
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 |
---|---|
DE1444049A1 (de) | 1969-02-06 |
LU44939A1 (xx) | 1964-02-04 |
NL301450A (xx) | |
CH1495863A4 (xx) | 1969-10-15 |
GB1067496A (en) | 1967-05-03 |
BE640919A (xx) | 1964-04-01 |
ES293757A1 (es) | 1964-04-16 |
CH485065A (fr) | 1970-01-31 |
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