WO2001023663A1 - Formaldehyde-free flame retardant treatment for cellulose-containing materials - Google Patents

Formaldehyde-free flame retardant treatment for cellulose-containing materials Download PDF

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Publication number
WO2001023663A1
WO2001023663A1 PCT/US2000/026133 US0026133W WO0123663A1 WO 2001023663 A1 WO2001023663 A1 WO 2001023663A1 US 0026133 W US0026133 W US 0026133W WO 0123663 A1 WO0123663 A1 WO 0123663A1
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WO
WIPO (PCT)
Prior art keywords
composition
cellulose
treated
flame retardant
aqueous finishing
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.)
Ceased
Application number
PCT/US2000/026133
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English (en)
French (fr)
Inventor
Jeffrey K. Stowell
Edward D. Weil
William L. Coble
Charles Q. Yang
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.)
Akzo Nobel NV
University of Georgia Research Foundation Inc
Original Assignee
Akzo Nobel NV
University of Georgia Research Foundation Inc
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 Akzo Nobel NV, University of Georgia Research Foundation Inc filed Critical Akzo Nobel NV
Priority to MXPA02003180A priority Critical patent/MXPA02003180A/es
Priority to EP00963746A priority patent/EP1226302B1/en
Priority to DE60038689T priority patent/DE60038689D1/de
Priority to CA002388781A priority patent/CA2388781A1/en
Priority to HK02108803.8A priority patent/HK1047150A1/zh
Priority to JP2001527037A priority patent/JP2003510478A/ja
Priority to AU40242/01A priority patent/AU4024201A/en
Publication of WO2001023663A1 publication Critical patent/WO2001023663A1/en
Anticipated expiration legal-status Critical
Ceased 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
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/244—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus
    • D06M13/282—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus with compounds containing phosphorus
    • D06M13/292—Mono-, di- or triesters of phosphoric or phosphorous acids; Salts thereof
    • 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
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
    • D06M13/184—Carboxylic acids; Anhydrides, halides or salts thereof
    • D06M13/192—Polycarboxylic acids; Anhydrides, halides or salts thereof
    • 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
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
    • D06M13/184—Carboxylic acids; Anhydrides, halides or salts thereof
    • D06M13/207—Substituted carboxylic acids, e.g. by hydroxy or keto groups; Anhydrides, halides or salts thereof
    • 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
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/244—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus
    • D06M13/282—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus with compounds containing phosphorus
    • D06M13/288—Phosphonic or phosphonous acids or derivatives thereof
    • 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
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/244—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus
    • D06M13/282—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus with compounds containing phosphorus
    • D06M13/292—Mono-, di- or triesters of phosphoric or phosphorous acids; Salts thereof
    • D06M13/295—Mono-, di- or triesters of phosphoric or phosphorous acids; Salts thereof containing polyglycol moieties; containing neopentyl moieties
    • 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
    • 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
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/667—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing phosphorus in the main chain
    • 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
    • Y10S57/00—Textiles: spinning, twisting, and twining
    • Y10S57/904—Flame retardant

Definitions

  • the present invention relates to a formaldehyde-free flame retardant treatment for cellulose-containing materials, such as cotton or cotton blends (e.g., cotton/polyester and cotton/nylon) , which is durable to both laundering and dry cleaning operations .
  • cellulose-containing materials such as cotton or cotton blends (e.g., cotton/polyester and cotton/nylon)
  • FR flame retardant
  • the PROBAN technology from Albright & Wilson, is based on the use of tetrakis- (hydroxymethyl)phosphonium chloride ("THPC")- based products and an ammoniation chamber. It is described in detail in the following U.S. Pat. Nos. 4,078,101; 4,145,463; 4,311,855 and 4,494,951, all to Albright and Wilson.
  • the PYROVATEX CP methodology originally developed by Ciba-Geigy, utilizes dimethyl (N- hydroxymethylcarbamoyl-ethyl)phosphonate or a similar methylol-functional phosphorus-containing analogue as the flame retardant agent.
  • the PYROVATEX technology suffers from much the same sort of downfalls as the PROBAN technology. Whether it is the original PYROVATEX CP methodology, based on the use of dimethyl (N-hydroxymethylcarbamoyl- ethyl)phosphonate, or other methods using different N- methylol-functional phosphorus-containing analogs, all of the products contain and emit the toxic component formaldehyde (a known carcinogen) .
  • a formaldehyde-containing cross-linking resin such as a N-methylolurea (for example, 1 , 3-dimethylol- 4,5-dihydroxyethyleneurea - "DMDHEU”) , N-methylolamide , or N-methylolmelamine , is also required to ensure adequate durability of the chemical finish.
  • N-methylolurea for example, 1 , 3-dimethylol- 4,5-dihydroxyethyleneurea - "DMDHEU”
  • N-methylolamide for example, 3-dimethylol- 4,5-dihydroxyethyleneurea - "DMDHEU”
  • N-methylolmelamine N-methylolmelamine
  • the present invention relates to an aqueous finishing composition for cellulose-containing materials and the materials treated with such a composition.
  • the aqueous finishing composition in its broadest embodiment, comprises a hydroxyalkyl-functional organophosphorus flame retardant and a non-formaldehyde cross-linking agent, optionally with a cross-linking catalyst also being included therein.
  • the aqueous finishing composition which is intended to be used to treat cellulose-containing materials in accordance with the present invention contains two essential components: (1) a hydroxyalkyl-functional organophosphorus flame retardant (excluding N-methylol , ethers thereof, and potentially formaldehyde releasing reagents) ; and (2) a non-formaldehyde cross-linking agent .
  • Monomeric, oligomeric (which generally contain from about two to ten repeat units) and polymeric (which generally contain over about ten repeat units) hydroxyalkyl-functional organophosphorus flame retardant additives are intended for use herein .
  • Fearing is an example of one of the hydroxyalkyl-functional organophosphorus flame retardants that can be used in accordance with the present invention .
  • a preferred embodiment has the following structure:
  • Ri is independently selected from methyl and hydroxyethyl
  • R 2 is independently selected from methyl, methoxy, and hydroxyethoxy
  • n is equal to or greater than 1.
  • This embodiment is made by a multistep process from dimethyl methylphosphonate , phosphorus pentoxide , ethylene glycol , and ethylene oxide and is available under the registered trademark FYROL 51 from Akzo Nobel Chemicals Inc .
  • the endgroups are principally hydroxyl groups .
  • Another class of materials for use herein includes water soluble oligomeric alkenylphosphonate materials , examples of which are described in U.S. Patent Nos . 3,855,359 and 4,017,257, both to E.D. Weil.
  • alkenyl substituents in these materials provide an additional mechanism for permanence utilizing free radical curing conditions (described in the patents above) .
  • a preferred species of this type was available under the trademark FYROL® 76 from Akzo Nobel Chemicals Inc. and is produced by reacting bis (2-chloroethyl) vinylphosphonate and dimethyl methylphosphonate with the substantial elimination of methyl chloride .
  • hydroxyalkyl-functional organophosphorus flame retardant that can be employed are oligomeric phosphoric acid esters that carry hydroxyalkoxy groups as described in U.S. Patent Nos . 2,909,559, 3,099,676, 3,228,998, 3,309,427, 3,472,919, 3,767,732, 3,850,859, 4,244,893, 4,382,042, 4,458,035, 4,697,030, 4,820,854, 4,886,895, 5,117,033, and 5,608,100.
  • the flame retardant is generally present at from about 1% to about 60%, preferably from about 10% to about 40%, by weight of the aqueous finshing composition.
  • the non-formaldehyde cross-linking agent which is the second essential component of the aqueous finishing composition of the present invention, is generally present at from about 1% to about 40%, by weight, of the total weight of that composition, preferably from about 5% to about 20%.
  • Polycarboxylic acid cross-linking agents form one type of cross-linking agent for use herein.
  • the polycarboxylic acids effective as cellulose cross-linking agents in regard to this invention include aliphatic, alicyclic and aromatic acids either olefinically saturated or unsaturated with at least three and preferably more carboxyl groups per molecule or with two carboxyl groups per molecule if a carbon-carbon double bond is present alpha, beta to one or both carboxyl groups .
  • a given carboxyl group in an aliphatic or alicyclic polycarboxylic acid should be separated from a second carboxyl group by no less than two carbon atoms and no more than three carbon atoms .
  • a carboxyl group In an aromatic acid, a carboxyl group must be ortho to a second carboxyl group if the first carboxyl is to be effective in esterifying cellulosic hydroxyl groups . It appears from these requirements that for a carboxyl group to be reactive, it should be able to form a cyclic 5-or 6-membered anhydride ring with a neighboring carboxyl group in the polycarboxylic acid molecule .
  • the aliphatic or alicyclic polycarboxylic acid may also contain an oxygen or sulfur atom in the chain or ring to which the carboxyl groups are attached.
  • a hydroxyl group attached to a carbon atom alpha to a carboxyl group does not interfere with the esterification and cross-linking of cellulose by the acid.
  • the presence of the hydroxyl group may cause a noticeable yellowing of the material during the heat cure .
  • Such an alpha-hydroxy acid is suitable for durable press finishing of suitably dyed cotton fabric, since the color of the dye conceals the discoloration that may be caused by the presence of the hydroxyl group.
  • Fabric discoloration is similarly observed with an unsaturated acid having an olefinic double bond that is not only alpha, beta to one carboxyl group but also beta, gamma to a second carboxyl group.
  • a particularly preferred polycarboxylic acid cross- linking agent for use herein is 1 ,2 , 3 , 4-butanetetra- carboxylic acid.
  • Another preferred polycarboxylic acid cross-linking agent for use herein is polymaleic acid.
  • this component is a hydrolyzed terpolymer of maleic anhydride with vinyl acetate and ethyl acrylate .
  • the molar ratio of maleic anhydride to the combined moles of vinyl acetate and ethyl acrylate is preferably from about 2.5:1 to about 5 : 1 and the molar amount of vinyl acetate to ethyl acrylate is preferably from about 1:4 to about 4:1, most preferably from about 1:2 to about 2:1.
  • the molecular weight of the terpolymer has an upper limit of about 4,000.
  • a product of this type is available under the trademark BELCLENE 283 from FMC Corporation.
  • Examples of other specific polycarboxylic acids which fall within the scope of this invention are the following: maleic acid; citraconic acid also called methylmaleic acid; citric acid also known as 2-hydroxy- 1 , 2 , 3-propanetri-carboxylic acid; itaconic acid also called methylenesuccinic acid; tricarballylic acid also known as 1 ,2 , 3, -propanetri-carboxylic acid; trans- aconitic acid also known as trans-l-propene-1 ,2 ,3- tricarboxylic acid; 1 ,2 ,3 ,4-butanetetra-carboxylic acid; all-cis-1 ,2 , 3, 4-cyclopentanetetracarboxylic acid; mellitic acid also known as benzenehexacarboxylic acid; oxydisuccinic acid also known as 2 ,2 ' -oxybis- (butanedioic acid) ; thiodisuccin
  • 4,820,307, 4,936,865, 4,975,209, and 5,221,285 include one or more of the alkali metal salts of the known hypophosphite, phosphite, pyrophosphate , dihydrogen phosphate , phosphate , and hydrogen phosphate species , and such acids as one or more of the polyphosphoric , hypophosphorous , phosphorous , and alkyl phosphinic acids.
  • Alternative basic cross-linking catalysts such as NaHC0 3 and Na 2 C0 3 can also be used.
  • a portion of the polycarboxylic acid may be used in salt form, especially as a water soluble salt. Suitable for this purpose are alkali metal salts of the acid.
  • the pH of the treating solution may be raised, or the solution partially neutralized, by the addition of a base, preferably a water soluble base, such as an alkali metal hydroxide, ammonium hydroxide , or an amine .
  • the pH may be elevated for such purpose to about 2.3 to about 5 , preferably about 2.5 to 4.
  • PEEOP is a poly (ethyl ethyleneoxy) phosphate of the type described in U.S. Serial No. 08/677,283, having a molecular weight of around 915 (number average) /1505 (weight average) , and a typical hydroxyl number of under about 5 mg KOH/g (low hydroxyl number version) and about 150 mg KOH/g (high hydroxyl number version) .
  • the modified FYROL 51 flame retardant has a hydroxyl number of under about 5 mg KOH/g and the high hydroxyl version of the FYROL ® 51 brand product has a hydroxyl number of about 125 mg KOH/g.
  • FYROL * 6 flame retardant has a hydroxyl number of about
  • Belclene 200 a 35% aqueous solution of polymaleic acid (PMA) .
  • BTCA 1 ,2 ,3, 4-butanetetracarboxylic acid (solid).
  • NaH 2 P0 2 (hydrate) used as a cross-linking catalyst .
  • Pad Applicator an instrument used to apply a solution to fabric at a specified level (% wet-pickup) .
  • Curing Oven (laboratory size) : an oven that is used to dry and subsequently cure chemically treated fabrics at high temperatures .
  • Washing Machine (household size) : used for laundering (with Tide detergent) fabrics before and after chemical treatment and curing .
  • each application solution was used within a period of five hours .
  • Each solution was then applied to a fabric sample .
  • the fabric was immersed in the solution, fed through the pad applicator, immersed in the solution again, and fed through the pad applicator again to ensure adequate homogeneity throughout the fabric sample .
  • each fabric sample was placed on a metal frame and inserted into the oven at 80°C to dry (three to five minutes) .
  • Each fabric sample was held in a horizontal position and ignited with a propane lighter. The flammability properties of each fabric sample were recorded.
  • Sample Compound #4 (20% add-on) with TMPA, BTCA, and PMA (samples - before washing, after one water wash, and after five launderings) .
  • Sample Compound #6 (20% add-on) with TMPA and BTCA (samples - before washing, after one water wash, and after five launderings) .
  • Sample Compound #5 (40% add-on) with TMPA, BTCA, and PMA (samples - after one water wash) .
  • ⁇ Numbers are blank corrected (sodium level in blank was ⁇ 75 ppm)

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Paper (AREA)
  • Fireproofing Substances (AREA)
  • Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Chemical And Physical Treatments For Wood And The Like (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
PCT/US2000/026133 1999-09-27 2000-09-22 Formaldehyde-free flame retardant treatment for cellulose-containing materials Ceased WO2001023663A1 (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
MXPA02003180A MXPA02003180A (es) 1999-09-27 2000-09-22 Tratamiento pirorretardante libre de formaldehido para materiales que contienen celulosa..
EP00963746A EP1226302B1 (en) 1999-09-27 2000-09-22 Formaldehyde-free flame retardant treatment for cellulose-containing materials
DE60038689T DE60038689D1 (de) 1999-09-27 2000-09-22 Formaldehydfreie flammfestausrüstung von cellulose enthaltenden materialien
CA002388781A CA2388781A1 (en) 1999-09-27 2000-09-22 Formaldehyde-free flame retardant treatment for cellulose-containing materials
HK02108803.8A HK1047150A1 (zh) 1999-09-27 2000-09-22 用於含纖維素材料的無甲醛阻燃處理
JP2001527037A JP2003510478A (ja) 1999-09-27 2000-09-22 セルロース含有物質のためのホルムアルデヒドを含まない難燃処理
AU40242/01A AU4024201A (en) 1999-09-27 2000-09-22 Formaldehyde-free flame retardant treatment for cellulose-containing materials

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US09/406,529 US6309565B1 (en) 1999-09-27 1999-09-27 Formaldehyde-free flame retardant treatment for cellulose-containing materials
US09/406,529 1999-09-27

Publications (1)

Publication Number Publication Date
WO2001023663A1 true WO2001023663A1 (en) 2001-04-05

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PCT/US2000/026133 Ceased WO2001023663A1 (en) 1999-09-27 2000-09-22 Formaldehyde-free flame retardant treatment for cellulose-containing materials

Country Status (12)

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US (2) US6309565B1 (https=)
EP (1) EP1226302B1 (https=)
JP (1) JP2003510478A (https=)
KR (1) KR100701717B1 (https=)
CN (1) CN1189618C (https=)
AT (1) ATE393258T1 (https=)
AU (1) AU4024201A (https=)
CA (1) CA2388781A1 (https=)
DE (1) DE60038689D1 (https=)
HK (1) HK1047150A1 (https=)
MX (1) MXPA02003180A (https=)
WO (1) WO2001023663A1 (https=)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6841198B2 (en) 2001-10-18 2005-01-11 Strike Investments, Llc Durable press treatment of fabric
US6989035B2 (en) 2001-10-18 2006-01-24 The Procter & Gamble Company Textile finishing composition and methods for using same
US7008457B2 (en) 2001-10-18 2006-03-07 Mark Robert Sivik Textile finishing composition and methods for using same
US7018422B2 (en) 2001-10-18 2006-03-28 Robb Richard Gardner Shrink resistant and wrinkle free textiles
US7144431B2 (en) 2001-10-18 2006-12-05 The Procter & Gamble Company Textile finishing composition and methods for using same
US7169742B2 (en) 2001-10-18 2007-01-30 The Procter & Gamble Company Process for the manufacture of polycarboxylic acids using phosphorous containing reducing agents
CN105401409A (zh) * 2015-11-27 2016-03-16 苏州大学 一种耐久型阻燃真丝的制备方法

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6491727B1 (en) 1999-06-09 2002-12-10 Cotton Incorporated Methods for reducing the flammability of cellulosic substrates
US7169293B2 (en) * 1999-08-20 2007-01-30 Uop Llc Controllable space velocity reactor and process
US6524653B1 (en) * 2000-11-01 2003-02-25 Niponi, Llc Cellulose-based fire retardant composition
AU2003215331A1 (en) * 2002-02-22 2003-09-09 University Of Georgia Research Foundation Catalyst system andmethod for preparing flame resistant materials
US7384881B2 (en) * 2002-08-16 2008-06-10 H.B. Fuller Licensing & Financing, Inc. Aqueous formaldehyde-free composition and fiberglass insulation including the same
US7168231B1 (en) 2002-09-05 2007-01-30 Samson Rope Technologies High temperature resistant rope systems and methods
US20050118919A1 (en) * 2002-10-01 2005-06-02 Eberhard Link Flame blocking liner materials
US20090233075A1 (en) * 2002-10-01 2009-09-17 Freudenberg Nonwovens Limited Partnership Flame Blocking Liner Materials
US20050054553A1 (en) * 2003-06-27 2005-03-10 The Procter & Gamble Company Liquid fabric softening compositions comprising flame retardant
JP3998251B2 (ja) * 2003-07-22 2007-10-24 竹本油脂株式会社 合成繊維用処理剤及び合成繊維の処理方法
US20050085145A1 (en) * 2003-10-21 2005-04-21 Xinggao Fang Flame resistant
US7134267B1 (en) 2003-12-16 2006-11-14 Samson Rope Technologies Wrapped yarns for use in ropes having predetermined surface characteristics
US7127878B1 (en) 2003-12-16 2006-10-31 Samson Rope Technologies Controlled failure rope systems and methods
DE10361878A1 (de) * 2003-12-19 2005-07-14 Ami-Agrolinz Melamine International Gmbh Flammschutzmischung für lignocellulosische Verbundstoffe
US20060141890A1 (en) * 2004-10-28 2006-06-29 Eberhard Link Ultrasonic lamination
WO2006137925A2 (en) * 2004-10-29 2006-12-28 Freudenberg Nonwovens, L.P. Deep draw process for flame retardant materials
US20060202175A1 (en) * 2005-03-10 2006-09-14 Yang Charles Q Flame retarding system for nylon fabrics
US7837009B2 (en) * 2005-04-01 2010-11-23 Buckeye Technologies Inc. Nonwoven material for acoustic insulation, and process for manufacture
CN102963107B (zh) 2005-04-01 2015-09-23 博凯技术公司 用于隔音的非织造材料和制造工艺
DE102005015196A1 (de) * 2005-04-02 2006-10-05 Ciba Spezialitätenchemie Pfersee GmbH Verfahren zur flammhemmenden Ausrüstung von Faserprodukten
US8341930B1 (en) 2005-09-15 2013-01-01 Samson Rope Technologies Rope structure with improved bending fatigue and abrasion resistance characteristics
US20070178788A1 (en) * 2005-12-07 2007-08-02 Freudenberg Nonwovens, L.P. Elastic Fire Blocking Materials
EP1973628B1 (en) 2006-01-18 2020-08-05 Georgia-Pacific Nonwovens LLC Tacky allergen trap and filter medium, and method for containing allergens
KR100681483B1 (ko) 2006-03-28 2007-02-12 한국과학기술연구원 환경친화성 셀룰로오즈계 난연 소재 및 이의 제조방법
WO2008005936A2 (en) 2006-06-30 2008-01-10 Buckeye Technologies Inc. Fire retardant nonwoven material and process for manufacture
US8080488B2 (en) * 2008-03-10 2011-12-20 H. B. Fuller Company Wound glass filament webs that include formaldehyde-free binder compositions, and methods of making and appliances including the same
US8109072B2 (en) 2008-06-04 2012-02-07 Samson Rope Technologies Synthetic rope formed of blend fibers
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US8689534B1 (en) 2013-03-06 2014-04-08 Samson Rope Technologies Segmented synthetic rope structures, systems, and methods
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US10736433B2 (en) 2013-07-29 2020-08-11 Fine Cotton Factory Inc. Fire resistant fabric
US9573661B1 (en) 2015-07-16 2017-02-21 Samson Rope Technologies Systems and methods for controlling recoil of rope under failure conditions
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US10377607B2 (en) 2016-04-30 2019-08-13 Samson Rope Technologies Rope systems and methods for use as a round sling

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3975154A (en) * 1975-06-09 1976-08-17 The United States Of America As Represented By The Secretary Of Agriculture Process for producing and utilizing durable press fabrics with strong acid grafts
US4220610A (en) * 1978-02-14 1980-09-02 Hoechst Aktiengesellschaft Organic phosphorus compounds with 2-hydroxyalkyl-phosphonic acid groups
US5273549A (en) * 1990-10-30 1993-12-28 Societe Francaise Hoechst Alkanepolycarboxylic acid derivatives as cross-linking agents of cellulose, new derivatives and textile finishes
US5320785A (en) * 1990-08-03 1994-06-14 Ciba-Geigy Corporation Compositions containing phosphono compounds and organic acids as flameproofing agents
US5695528A (en) * 1994-07-13 1997-12-09 Nippon Chemical Industrial Co., Ltd. Treating agent for cellulosic textile material and process for treating cellulosic textile material
WO2000029662A1 (en) * 1998-11-13 2000-05-25 Cotton Incorporated Methods for reducing the flammability of cellulosic substrates

Family Cites Families (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3695925A (en) * 1970-03-27 1972-10-03 Stauffer Chemical Co Process for flameproofing textiles
US4268633A (en) * 1978-04-20 1981-05-19 Stauffer Chemical Company Polyurethanes containing a poly (oxyorganophosphate/phosphonate) flame retardant
US4199534A (en) * 1978-04-20 1980-04-22 Stauffer Chemical Company Poly (oxyorganophosphate/phosphonate) and process for preparing
US4335178A (en) * 1979-09-10 1982-06-15 Stauffer Chemical Company Textiles containing a poly(oxyorganophosphate/phosphonate) flame retardant
US4443903A (en) 1981-08-31 1984-04-24 Stauffer Chemical Company Composite upholstered furniture or mattress assembly with flame retardant-smolder resistant textile backcoated fabric layer
US4444831A (en) 1981-08-31 1984-04-24 Stauffer Chemical Company Flame retardant-smolder resistant textile backcoating
US4404313A (en) 1981-08-31 1983-09-13 Stauffer Chemical Company Flame retardant-smolder resistant textile backcoating
JPS63190080A (ja) * 1987-01-29 1988-08-05 小松精練株式会社 繊維材料の処理方法
US4936865A (en) 1988-06-16 1990-06-26 The United States Of America As Represented By The Secretary Of Agriculture Catalysts and processes for formaldehyde-free durable press finishing of cotton textiles with polycarboxylic acids
US5221285A (en) 1988-06-16 1993-06-22 The United States Of America As Represented By The Secretary Of Agriculture Catalysts and processes for formaldehyde-free durable press finishing of cotton textiles with polycarboxylic acids, and textiles made therewith
US4975209A (en) 1988-06-16 1990-12-04 The United States Of America As Represented By The Secretary Of Agriculture Catalysts and processes for formaldehyde-free durable press finishing of cotton textiles with polycarboxylic acids
US4820307A (en) 1988-06-16 1989-04-11 The United States Of America As Represented By The Secretary Of Agriculture Catalysts and processes for formaldehyde-free durable press finishing of cotton textiles with polycarboxylic acids
US5116890A (en) * 1989-06-26 1992-05-26 Sequa Chemicals, Inc. Non-formaldehyde self-crosslinking latex
US5199953A (en) 1990-09-14 1993-04-06 Ortec, Inc. Process for reducing discoloration of cellulosic fibers, treated at a high temperature with a solution of a polycarboxylic acid and boric acid or borate
US5252663A (en) * 1991-05-22 1993-10-12 National Starch And Chemical Investment Holding Corporation Formaldehyde-free crosslinking emulsion polymer systems based on vinyl ester dialkoxyhydroxyethyl acrylamide co- and terpolymers
DE4117902A1 (de) * 1991-05-31 1992-12-03 Basf Ag Katalysator fuer die hochveredlung von textilien
JPH06101176A (ja) * 1992-02-18 1994-04-12 Teijin Ltd セルロース系繊維材料の耐久性防炎加工法
US5447537A (en) * 1992-04-06 1995-09-05 Board Of Supervisors Of Louisiana State University And Agricultural And Mechanical College Cotton fabrics with improved strength retention
EP0572923A1 (de) * 1992-06-02 1993-12-08 Hoechst Aktiengesellschaft Verfahren zur formaldehydfreien Pflegeleicht-Ausrüstung von cellulosehaltigem Textilgut
US5496476A (en) 1992-12-21 1996-03-05 Ppg Indutstries, Inc. Non-formaldehyde durable press finishing for cellulosic textiles with phosphonoalkylpolycarboxylic acid
DE19606394A1 (de) 1996-02-21 1997-08-28 Basf Ag Formaldehydfreie, wäßrige Bindemittel
US6165919A (en) 1997-01-14 2000-12-26 University Of Georgia Research Foundation, Inc. Crosslinking agents of cellulosic fabrics

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3975154A (en) * 1975-06-09 1976-08-17 The United States Of America As Represented By The Secretary Of Agriculture Process for producing and utilizing durable press fabrics with strong acid grafts
US4220610A (en) * 1978-02-14 1980-09-02 Hoechst Aktiengesellschaft Organic phosphorus compounds with 2-hydroxyalkyl-phosphonic acid groups
US5320785A (en) * 1990-08-03 1994-06-14 Ciba-Geigy Corporation Compositions containing phosphono compounds and organic acids as flameproofing agents
US5273549A (en) * 1990-10-30 1993-12-28 Societe Francaise Hoechst Alkanepolycarboxylic acid derivatives as cross-linking agents of cellulose, new derivatives and textile finishes
US5695528A (en) * 1994-07-13 1997-12-09 Nippon Chemical Industrial Co., Ltd. Treating agent for cellulosic textile material and process for treating cellulosic textile material
WO2000029662A1 (en) * 1998-11-13 2000-05-25 Cotton Incorporated Methods for reducing the flammability of cellulosic substrates

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
WELCH C M: "FORMALDEHYDE-FREE DURABLE-PRESS FINISHES", REVIEW OF PROGRESS IN COLORATION & RELATED TOPICS,GB,SOCIETY OF DYERS AND COLOURISTS. BRADFORD, vol. 22, 1992, pages 32 - 41, XP000305372, ISSN: 0557-9325 *

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6841198B2 (en) 2001-10-18 2005-01-11 Strike Investments, Llc Durable press treatment of fabric
US6989035B2 (en) 2001-10-18 2006-01-24 The Procter & Gamble Company Textile finishing composition and methods for using same
US7008457B2 (en) 2001-10-18 2006-03-07 Mark Robert Sivik Textile finishing composition and methods for using same
US7018422B2 (en) 2001-10-18 2006-03-28 Robb Richard Gardner Shrink resistant and wrinkle free textiles
US7144431B2 (en) 2001-10-18 2006-12-05 The Procter & Gamble Company Textile finishing composition and methods for using same
US7169742B2 (en) 2001-10-18 2007-01-30 The Procter & Gamble Company Process for the manufacture of polycarboxylic acids using phosphorous containing reducing agents
US7247172B2 (en) 2001-10-18 2007-07-24 The Procter & Gamble Company Shrink resistant and wrinkle free textiles
CN105401409A (zh) * 2015-11-27 2016-03-16 苏州大学 一种耐久型阻燃真丝的制备方法

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