US2832745A - Aqueous flameproofing compositions and cellulosic materials treated therewith - Google Patents

Aqueous flameproofing compositions and cellulosic materials treated therewith Download PDF

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US2832745A
US2832745A US607300A US60730056A US2832745A US 2832745 A US2832745 A US 2832745A US 607300 A US607300 A US 607300A US 60730056 A US60730056 A US 60730056A US 2832745 A US2832745 A US 2832745A
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phosphate
adduct
cellulosic materials
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materials treated
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Hechenbleikner Ingenuin
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Columbia Chemical Corp
Shea Chemical Corp
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Shea Chemical Corp
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    • 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
    • D06M13/244—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
    • 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
    • D06M15/39—Aldehyde resins; Ketone resins; Polyacetals
    • D06M15/423—Amino-aldehyde resins
    • D06M15/43—Amino-aldehyde resins modified by phosphorus compounds
    • D06M15/433—Amino-aldehyde resins modified by phosphorus compounds by phosphoric acids
    • 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
    • Y10S428/00—Stock material or miscellaneous articles
    • Y10S428/92—Fire or heat protection feature
    • Y10S428/921—Fire or flameproofing
    • 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
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
    • Y10T442/2631—Coating or impregnation provides heat or fire protection
    • Y10T442/2672—Phosphorus containing
    • Y10T442/268—Phosphorus and nitrogen containing compound

Definitions

  • the present invention relates to the novel flame-proofing compositions, flammable materials treated therewith and methods of treating such flammable materials to render them flameproof.
  • An additional object is to flameproof cellulosic materials in a manner to impart increased permanence to laundering.
  • a further object is to devise a more economic cellulosic fabric flameproofing composition.
  • Yet another object is to eliminate the tendering of cellulosic fabrics imparted by the application diethylphosphoramidate (diethyl amido phosphate) and a polymethylol compound thereto.
  • composition comprising (1) a compound having the formula 0 RiOIlI OR: or Rr0-NHI NH: NH: where R and R are alkyl or haloalkyL the sum of the carbon atoms in R and R being less than 8, (2) the adduct of a compound having the formula CX YZ, where X is chlorine or bromine, and Y and Z are hydrogen, chlorine or bromine with either a polymerizable neutral unsaturated alcohol ester of phosphoric acid or of an alkene phosphonic acid and (3) a polymethylol amide, azine or azole.
  • the preferred combination is the use of (l) diethyl phosphoramidate phosphoramidate 2,832,745 Patented Apr. 29, 1958 (2) the 1 to 1 mol ratio bromoform adduct of triallyl phosphate and (3) trimethylolmelamine. It is surprising that the present composition can be successfully applied to cellulosic materials as the combination of diethyl and trimethylolmelamine alone causes severe tendering of cellulosic fabrics, imparting a stiff board-like quality to the fabric.
  • the novel compositions of the present invention have improved flexibility and superior flameproofing qualities.
  • the flameproofing compositions of. this invention are preferably applied as aqueous dispersions.
  • the objects to be flameproofed are cellulosic in nature, e. g., cotton textiles, regenerated cellulose fabrics, acetate rayon.
  • amidophosphates having less than eight carbon atoms there can be used diethyl amido phosphate, dipropyl amido phosphate, ethyl propyl amido phosphate, amyl diamido phosphate, di-2-chloroethylamido phosphate, di-2-bromoethylamido phosphate, diisopropyl amido phosphate, ethyl diamido phosphate, propyl diamido phosphate, 2-chloroethyl amido phosphate, etc.
  • adduct of the compound having the formula CX YZ with the phosphate ester there can be employed any of the adducts set forth in Frick et al. Patent 2,686,769, e. g., the adducts of CBr CB1' C1, CBr Cl CBIC13, CBI'3H, CB1'2H2, C014, or CClzHz neutral unsaturated alcohol esters of phosphoric acid such as trialkenyl phosphates, e. g., triallyl phosphate, trimethyllyl phosphate, triethallyl phosphate, diallyl phosphate, methyl divinyl phosphate, methallyl phosphate, etc.
  • trialkenyl phosphates e. g., triallyl phosphate, trimethyllyl phosphate, triethallyl phosphate, diallyl phosphate, methyl divinyl phosphate, methallyl phosphate, etc.
  • polymerizable neutral unsaturated alcohol esters of alkene phosphonic acids e. g., diallyl propene-2-phosphonate, dimethallyl propene-Z-phosphonate, diethallyl propene-2- phosphonate, allyl methallyl propene-Z-phosphonate, etc.
  • These phosphonates can be prepared in the manner set forth in Kosolapoff reaction method IA, pages 121-123 and the references cited therein.
  • the preferred adduct is the 1 to 1 mol ratio adduct of bromoform with triallyl phosphate.
  • polymethylol amide, azine or azole there can be used the formaldehyde reaction products with amides such as urea, thiourea, guanidine, dicyandiami'de, substituted ureas, e. g., methyl urea, ethylene diurea, decamethylene diurea, methylene diurea, oxamide, acetamide, malonie acid amide, phthalamide, 'succinic acid amide, biuret, sulfamide, toluene sulfonamide.
  • amides or substituted ureas disclosed in DAlelio, United States Patent No. 2,320,816.
  • reaction products of formaldehyde with aminotriazines such as melamine, ammeline, formoguanamine, acetoguanamine, ammelide, benzoguanamine, sym-triphenyl melamine, sym-triethyl melamine, 2-chloro-4,6-diaminotriazine, diaminotriazin'e, melam, melon, melem, as well as any of the aldehyde reactable aminotriazines disclosed in DAlelio, United States Patent No. 2,368,451 and Widmer et al., United States Patent No. 2,197,357.
  • diazines e. g., 2,4-diamino-1,3-diazine, azoles, e. g.,
  • the amount of formaldehyde need not be more than suflicient to react with all the hydrogen atoms attached to the nitro mine is preferably applied to .a polymer, e; g. the
  • the bromoforrn adduct and the by the cloth is preferably in the range of about 1-1.5
  • the preferred compound for reaction with formaldehyde is melamine.
  • uct is trimethylol melamine.
  • the bromoform-triallyl phosphate adduct is preferably employed as The preferred reaction prod- Frick Patent 2,686,769.
  • the phosphorus deposited upon the cloth e. g., cotton
  • the diethyl phosphoramidate diethyl amidoph'osphate
  • the bromororm-triallyl phosphate (1 to 1 mol ratio) is preferably used in an amount of "0.25 to 0.5 mol per mol of trimethylol melamine.
  • the trirnethylol melamine and diethyl amidophosphate form a thermosetting resin within the textile fiber.
  • the bromoforrn-triallyl phosphate adduct modifies this composition to give increased flexibility and further gives some additional flame-proofing.
  • the reaction of the amidophosphate with the trimethylol melamine and cellulose is believed to proceed as follows:
  • Example 1 Cotton cloth was dipped in a solution prepared in the following manner:
  • the cloth was squeezed through a roll, cured for 3 minutes at 160 C. and dried at C.
  • the dry pick-up of the cloth was about 25%.
  • the dry pickup of the cotton cloth generally ranged from 20-30%.
  • any conventional acidic curing agent for melamine formaldehyde resins such as those shown in the Widmer patent for example.
  • the curing can be carried out by using temperatures below C. for longer than 3 minutes if desired.
  • the treated cotton cloth of Example I was fiameproof even after 20 launderings.
  • Example II Example I was repeated, replacing the cotton cloth with a regenerated cellulose (viscose) fabric. The fabric was also fiameproof even after 20 launderings.
  • a flameproofing composition comprising a mixture of (a) a compound selected from the group consisting of u RiOiI ORn and RrO?-NH2 NH: NH:
  • R and R are selected from the group consisting of alkyl monochloro alkyl and monobromo alkyl groups, the sum of the carbon atoms in R and R being less than 8, (b) the adduct of a compound having the formula CX YZ where X is a member of the group consisting of chlorine and bromine and Y and Z are selected from the group consisting of hydrogen, chlorine and bromine, with a compound from the group consisting of polymerizable, neutral, ethylenically unsaturated acyclic alcohol esters of phosphoric acid and polymerizable, neutral, ethylenically unsaturated acyclic alcohol esters of an alkene phosphonic acid and (c) a member of the group consisting of polymethylol amides, polymethylol azines and polymethylol azoles dispersed in water, compound (a) being used in amount of 1 to 1.5 mols per mol of compound (c) and adduct (b) being used in an amount
  • composition according to claim 1 wherein the polymethylolamide is a polymethylol urea.
  • composition according to claim 1 wherein the polymethylolamide is a polymethylol melamine.
  • a flameproofing composition comprising a mixture of 1 to 1.5 mols diethyl phosphoramidate, 0.25 to 0.5 mol of the adduct of bromoformwith triallyl phosphate and t 1 mol of a polymethylolmelamine dispersed in water.

Description

United States Patent AQUEOUS FLAMEPROOFING COMPOSITIONS AND CELLULOSIC MATERIALS TREATED THEREWITH Ingenuin Hechenbleikner, Adams, Mass., assignor to Shea Chemical Corporation, Jelfersonville, Ind., and Columbia, Tenu., a corporation of Maryland No Drawing. Application August 31, 1956 Serial No. 607,300
9 Claims. (Cl. 26.0-29.4)
The present invention relates to the novel flame-proofing compositions, flammable materials treated therewith and methods of treating such flammable materials to render them flameproof.
agent. However, the use of this compound leaves the fabric with relatively poor tear and tensile strength. The combination of THPC with the bromoform adduct previously referred to has the disadvantage of the relatively high cost due to the use of the THPC, the objectionable odor liberated by THPC and the relatively low phosphorus content in the THPC.
It is an object of the present invention to form an improved flameproofing composition.
An additional object is to flameproof cellulosic materials in a manner to impart increased permanence to laundering.
A further object is to devise a more economic cellulosic fabric flameproofing composition.
Yet another object is to eliminate the tendering of cellulosic fabrics imparted by the application diethylphosphoramidate (diethyl amido phosphate) and a polymethylol compound thereto.
Still further objects and the entire scope of applicability of the present invention will become apparent from the detailed description given hereinafter; it should be understood, however, that the detailed description and specific examples, while indicating preferred embodiments of the invention, are given by way of illustration only, since various changes and modifications within the spirit and scope of the invention will become apparent to those skilled in the art from this detailed description.
It has now been found that these objects can be attained by the use of a composition comprising (1) a compound having the formula 0 RiOIlI OR: or Rr0-NHI NH: NH: where R and R are alkyl or haloalkyL the sum of the carbon atoms in R and R being less than 8, (2) the adduct of a compound having the formula CX YZ, where X is chlorine or bromine, and Y and Z are hydrogen, chlorine or bromine with either a polymerizable neutral unsaturated alcohol ester of phosphoric acid or of an alkene phosphonic acid and (3) a polymethylol amide, azine or azole.
The preferred combination is the use of (l) diethyl phosphoramidate phosphoramidate 2,832,745 Patented Apr. 29, 1958 (2) the 1 to 1 mol ratio bromoform adduct of triallyl phosphate and (3) trimethylolmelamine. It is surprising that the present composition can be successfully applied to cellulosic materials as the combination of diethyl and trimethylolmelamine alone causes severe tendering of cellulosic fabrics, imparting a stiff board-like quality to the fabric. The novel compositions of the present invention, however, have improved flexibility and superior flameproofing qualities.
The flameproofing compositions of. this invention are preferably applied as aqueous dispersions. Preferably the objects to be flameproofed are cellulosic in nature, e. g., cotton textiles, regenerated cellulose fabrics, acetate rayon.
As examples of suitable amidophosphates having less than eight carbon atoms, there can be used diethyl amido phosphate, dipropyl amido phosphate, ethyl propyl amido phosphate, amyl diamido phosphate, di-2-chloroethylamido phosphate, di-2-bromoethylamido phosphate, diisopropyl amido phosphate, ethyl diamido phosphate, propyl diamido phosphate, 2-chloroethyl amido phosphate, etc. These compounds can be prepared in the manner set forth in Kosolapoff, Organophosphorus Compounds (1950), Reaction Method II, pages 279281, and the articles cited therein. The preferred amidophosphate or phosphonate is diethyl amido phosphate.
As the adduct of the compound having the formula CX YZ with the phosphate ester, there can be employed any of the adducts set forth in Frick et al. Patent 2,686,769, e. g., the adducts of CBr CB1' C1, CBr Cl CBIC13, CBI'3H, CB1'2H2, C014, or CClzHz neutral unsaturated alcohol esters of phosphoric acid such as trialkenyl phosphates, e. g., triallyl phosphate, trimethyllyl phosphate, triethallyl phosphate, diallyl phosphate, methyl divinyl phosphate, methallyl phosphate, etc. In place of the phosphates in forming the adducts with the CX YZ compounds, there can be used polymerizable neutral unsaturated alcohol esters of alkene phosphonic acids, e. g., diallyl propene-2-phosphonate, dimethallyl propene-Z-phosphonate, diethallyl propene-2- phosphonate, allyl methallyl propene-Z-phosphonate, etc. These phosphonates can be prepared in the manner set forth in Kosolapoff reaction method IA, pages 121-123 and the references cited therein. The preferred adduct is the 1 to 1 mol ratio adduct of bromoform with triallyl phosphate.
As the polymethylol amide, azine or azole, there can be used the formaldehyde reaction products with amides such as urea, thiourea, guanidine, dicyandiami'de, substituted ureas, e. g., methyl urea, ethylene diurea, decamethylene diurea, methylene diurea, oxamide, acetamide, malonie acid amide, phthalamide, 'succinic acid amide, biuret, sulfamide, toluene sulfonamide. There also can be used any of the amides or substituted ureas disclosed in DAlelio, United States Patent No. 2,320,816. Likewise, there can be used the reaction products of formaldehyde with aminotriazines such as melamine, ammeline, formoguanamine, acetoguanamine, ammelide, benzoguanamine, sym-triphenyl melamine, sym-triethyl melamine, 2-chloro-4,6-diaminotriazine, diaminotriazin'e, melam, melon, melem, as well as any of the aldehyde reactable aminotriazines disclosed in DAlelio, United States Patent No. 2,368,451 and Widmer et al., United States Patent No. 2,197,357. Likewise, there can be used diazines, e. g., 2,4-diamino-1,3-diazine, azoles, e. g.,
carbamyl .guanazole, guanazole, diamino pyrrole, etc.
amine, hexamethylol melamine, etc. Generally the amount of formaldehyde need not be more than suflicient to react with all the hydrogen atoms attached to the nitro mine is preferably applied to .a polymer, e; g. the
the bromoforrn adduct and the by the cloth is preferably in the range of about 1-1.5
gen atoms. The preferred compound for reaction with formaldehyde is melamine. uct is trimethylol melamine.
The mixture of the diethyl amido phosphate, bromoform adduct of triallyl phosphate and trimethylol melathe textile material in the form of an aqueous solution or dispersion. The bromoform-triallyl phosphate adduct is preferably employed as The preferred reaction prod- Frick Patent 2,686,769.
Preferably about 30-50% of the phosphorus deposited upon the cloth, e. g., cotton, should be contributed by total phosphorus pick-up of the total Weight of the cloth. The diethyl phosphoramidate (diethyl amidoph'osphate) is utilized in an amount of from 1 to 1.5 mols, e. g., 1.25 mols per mol of trimethylol melamine. The bromororm-triallyl phosphate (1 to 1 mol ratio) is preferably used in an amount of "0.25 to 0.5 mol per mol of trimethylol melamine.
It is believed that the trirnethylol melamine and diethyl amidophosphate form a thermosetting resin within the textile fiber. The bromoforrn-triallyl phosphate adduct modifies this composition to give increased flexibility and further gives some additional flame-proofing. The reaction of the amidophosphate with the trimethylol melamine and cellulose is believed to proceed as follows:
i NHCHzOH The methylol groups are then free to form ethers with cellulose and internal ethers with themselves. Both of the following types of reactions are believed to occur,
all percentages and parts are by weight.
Example 1 Cotton cloth was dipped in a solution prepared in the following manner:
1 part of diethyl phosphoramidate and 1 part of trimethylol melamine were dissolved in water. To the above solution there was added an equal weight of an emulsion made by mixing 252 parts of triallyl phosphate, 163 parts of bromoforrn, 12.5 parts of potassium persulfate, 85 parts of polyvinyl alcohol (medium viscosity), 22.5 parts of sodium bicarbonate and 850 parts of water. mechanically stirring the mixture until completely emulsified and then Warming the mixture at 85-90 C. for 2.5 hours with continuous stirring. (It should be noted that any of the emulsifying agents and catalysts described in Frick Patent 2,686,769 can be used in place of the polyvinyl alcohol and potassium persulfate of this example.)
The pH of the resulting mixture containing the diethyl polymer described in Example I of 'fiameproofed by phosphoramidate, trimethylolmelamine and polymerized bromoform-triallyl phosphate adduct was adjusted to 5-6 with phosphoric acid.
After the cotton cloth was dipped in the above mixture, the cloth was squeezed through a roll, cured for 3 minutes at 160 C. and dried at C. The dry pick-up of the cloth was about 25%.
In other examples carried out as this one, the dry pickup of the cotton cloth generally ranged from 20-30%.
In place of phosphoric acid, there can be employed any conventional acidic curing agent for melamine formaldehyde resins, such as those shown in the Widmer patent for example. The curing can be carried out by using temperatures below C. for longer than 3 minutes if desired.
The treated cotton cloth of Example I was fiameproof even after 20 launderings.
Example II Example I was repeated, replacing the cotton cloth with a regenerated cellulose (viscose) fabric. The fabric was also fiameproof even after 20 launderings.
I claim:
1. A flameproofing composition comprising a mixture of (a) a compound selected from the group consisting of u RiOiI ORn and RrO?-NH2 NH: NH:
where R and R are selected from the group consisting of alkyl monochloro alkyl and monobromo alkyl groups, the sum of the carbon atoms in R and R being less than 8, (b) the adduct of a compound having the formula CX YZ where X is a member of the group consisting of chlorine and bromine and Y and Z are selected from the group consisting of hydrogen, chlorine and bromine, with a compound from the group consisting of polymerizable, neutral, ethylenically unsaturated acyclic alcohol esters of phosphoric acid and polymerizable, neutral, ethylenically unsaturated acyclic alcohol esters of an alkene phosphonic acid and (c) a member of the group consisting of polymethylol amides, polymethylol azines and polymethylol azoles dispersed in water, compound (a) being used in amount of 1 to 1.5 mols per mol of compound (c) and adduct (b) being used in an amount of 0.25 to 0.5 mol of compound (c).
2. A normally inflammable material that has been impregnating the same with the compo sition of claim 1.
3. A composition according to claim 1 wherein the polymethylolamide is a polymethylol urea.
4. A composition according to claim 1 wherein the polymethylolamide is a polymethylol melamine.
5. A flameproofing composition comprising a mixture of 1 to 1.5 mols diethyl phosphoramidate, 0.25 to 0.5 mol of the adduct of bromoformwith triallyl phosphate and t 1 mol of a polymethylolmelamine dispersed in water.
References Cited in the file of this patent UNITED STATES PATENTS 2,574,516 Walter et al Nov. 13, .1951 2,582,961 'Burnell ct a1. Jan. 22, 1952 2,686,769 Frick et a] Aug. 17, 1954

Claims (1)

1. A FLAMEPROOFING COMPOSITION COMPRISING A MIXTURE OF (A) A COMPOUND SELECTED FROM THE GROUP CONSISTING OF
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Cited By (21)

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US3038924A (en) * 1958-02-24 1962-06-12 Philips Corp Bis(dimethylamido)pentachlorophenylphosphate and the thiolophenyl phosphate derivative thereof
US3068060A (en) * 1959-08-03 1962-12-11 Rohm & Haas Treatment of cellulose textiles with phosphoramides
US3087955A (en) * 1960-02-08 1963-04-30 Dow Chemical Co O-haloalkyl o-alkyl phosphoramidothioates
US3157568A (en) * 1959-02-16 1964-11-17 Philips Corp Bis(dimethylamido)pentachlorophenyl fungicidal compositions
US3240729A (en) * 1961-12-12 1966-03-15 Hoye Peter Albert Theodore Polyurethanes from phosphoramidates
US3527564A (en) * 1968-04-15 1970-09-08 Stevens & Co Inc J P Process for carbonizing fibrous materials
US3676389A (en) * 1970-06-12 1972-07-11 Polaris Chem Corp Flame proofing compositions
US4026808A (en) * 1972-03-30 1977-05-31 Hooker Chemicals & Plastics Corporation Flame retardant textile finishes
US4370442A (en) * 1980-12-05 1983-01-25 Pearson Glenn A Fire retardant compositions
US20080022645A1 (en) * 2006-01-18 2008-01-31 Skirius Stephen A Tacky allergen trap and filter medium, and method for containing allergens
US20080050565A1 (en) * 2005-04-01 2008-02-28 Buckeye Technologies Inc. Fire retardant nonwoven material and process for manufacture
US20080121461A1 (en) * 2005-04-01 2008-05-29 Gross James R Nonwoven material for acoustic insulation, and process for manufacture
US20090019825A1 (en) * 2007-07-17 2009-01-22 Skirius Stephen A Tacky allergen trap and filter medium, and method for containing allergens
US20100095846A1 (en) * 2006-01-18 2010-04-22 Buckeye Technologies Inc. Tacky allergen trap and filter medium, and method for containing allergens
US7918313B2 (en) 2005-04-01 2011-04-05 Buckeye Technologies Inc. Nonwoven material for acoustic insulation, and process for manufacture
WO2012018746A1 (en) 2010-08-03 2012-02-09 International Paper Company Addition of endothermic fire retardants to provide near neutral ph pulp fiber webs
WO2012018749A1 (en) 2010-08-03 2012-02-09 International Paper Company Fire retardant treated fluff pulp web and process for making same
EP2481744A1 (en) 2011-02-01 2012-08-01 EMPA Eidgenössische Materialprüfungs- und Forschungsanstalt Aromatic bis-phosphoramidate additives as flame retardants for polymers
US8388807B2 (en) 2011-02-08 2013-03-05 International Paper Company Partially fire resistant insulation material comprising unrefined virgin pulp fibers and wood ash fire retardant component
US8663427B2 (en) 2011-04-07 2014-03-04 International Paper Company Addition of endothermic fire retardants to provide near neutral pH pulp fiber webs
US20180002548A1 (en) * 2016-07-04 2018-01-04 Hyundai Motor Company Flame retardant treating agent for kapok-fiber or kapok-nonwoven fabric

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US3038924A (en) * 1958-02-24 1962-06-12 Philips Corp Bis(dimethylamido)pentachlorophenylphosphate and the thiolophenyl phosphate derivative thereof
US3157568A (en) * 1959-02-16 1964-11-17 Philips Corp Bis(dimethylamido)pentachlorophenyl fungicidal compositions
US3068060A (en) * 1959-08-03 1962-12-11 Rohm & Haas Treatment of cellulose textiles with phosphoramides
US3087955A (en) * 1960-02-08 1963-04-30 Dow Chemical Co O-haloalkyl o-alkyl phosphoramidothioates
US3240729A (en) * 1961-12-12 1966-03-15 Hoye Peter Albert Theodore Polyurethanes from phosphoramidates
US3527564A (en) * 1968-04-15 1970-09-08 Stevens & Co Inc J P Process for carbonizing fibrous materials
US3676389A (en) * 1970-06-12 1972-07-11 Polaris Chem Corp Flame proofing compositions
US4026808A (en) * 1972-03-30 1977-05-31 Hooker Chemicals & Plastics Corporation Flame retardant textile finishes
US4370442A (en) * 1980-12-05 1983-01-25 Pearson Glenn A Fire retardant compositions
US20080050565A1 (en) * 2005-04-01 2008-02-28 Buckeye Technologies Inc. Fire retardant nonwoven material and process for manufacture
US20080121461A1 (en) * 2005-04-01 2008-05-29 Gross James R Nonwoven material for acoustic insulation, and process for manufacture
US7918313B2 (en) 2005-04-01 2011-04-05 Buckeye Technologies Inc. Nonwoven material for acoustic insulation, and process for manufacture
US7837009B2 (en) 2005-04-01 2010-11-23 Buckeye Technologies Inc. Nonwoven material for acoustic insulation, and process for manufacture
US7878301B2 (en) 2005-04-01 2011-02-01 Buckeye Technologies Inc. Fire retardant nonwoven material and process for manufacture
US20080022645A1 (en) * 2006-01-18 2008-01-31 Skirius Stephen A Tacky allergen trap and filter medium, and method for containing allergens
US20100095846A1 (en) * 2006-01-18 2010-04-22 Buckeye Technologies Inc. Tacky allergen trap and filter medium, and method for containing allergens
US7727915B2 (en) 2006-01-18 2010-06-01 Buckeye Technologies Inc. Tacky allergen trap and filter medium, and method for containing allergens
US20090019825A1 (en) * 2007-07-17 2009-01-22 Skirius Stephen A Tacky allergen trap and filter medium, and method for containing allergens
WO2012018746A1 (en) 2010-08-03 2012-02-09 International Paper Company Addition of endothermic fire retardants to provide near neutral ph pulp fiber webs
WO2012018749A1 (en) 2010-08-03 2012-02-09 International Paper Company Fire retardant treated fluff pulp web and process for making same
US8685206B2 (en) 2010-08-03 2014-04-01 International Paper Company Fire retardant treated fluff pulp web and process for making same
US8871053B2 (en) 2010-08-03 2014-10-28 International Paper Company Fire retardant treated fluff pulp web
EP2481744A1 (en) 2011-02-01 2012-08-01 EMPA Eidgenössische Materialprüfungs- und Forschungsanstalt Aromatic bis-phosphoramidate additives as flame retardants for polymers
US8388807B2 (en) 2011-02-08 2013-03-05 International Paper Company Partially fire resistant insulation material comprising unrefined virgin pulp fibers and wood ash fire retardant component
US8663427B2 (en) 2011-04-07 2014-03-04 International Paper Company Addition of endothermic fire retardants to provide near neutral pH pulp fiber webs
US8871058B2 (en) 2011-04-07 2014-10-28 International Paper Company Addition of endothermic fire retardants to provide near neutral pH pulp fiber webs
US20180002548A1 (en) * 2016-07-04 2018-01-04 Hyundai Motor Company Flame retardant treating agent for kapok-fiber or kapok-nonwoven fabric

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