US3885912A - Method of rendering textiles flame retardant with phosphorus containing melamine - Google Patents

Method of rendering textiles flame retardant with phosphorus containing melamine Download PDF

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Publication number
US3885912A
US3885912A US401767A US40176773A US3885912A US 3885912 A US3885912 A US 3885912A US 401767 A US401767 A US 401767A US 40176773 A US40176773 A US 40176773A US 3885912 A US3885912 A US 3885912A
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Prior art keywords
compound
formula
article
flame retardant
percent
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US401767A
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English (en)
Inventor
Peter Golborn
James J Duffy
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Occidental Chemical Corp
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Hooker Chemicals and Plastics Corp
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Priority to GB1390973A priority Critical patent/GB1429004A/en
Priority to DE2315212A priority patent/DE2315212A1/de
Priority to FR7310952A priority patent/FR2178055A1/fr
Priority to BE129393A priority patent/BE797473A/xx
Priority to CA167,355A priority patent/CA1019756A/en
Priority to JP48036574A priority patent/JPS4915291A/ja
Priority to NL7304498A priority patent/NL7304498A/xx
Application filed by Hooker Chemicals and Plastics Corp filed Critical Hooker Chemicals and Plastics Corp
Priority to US401767A priority patent/US3885912A/en
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Publication of US3885912A publication Critical patent/US3885912A/en
Assigned to OCCIDENTAL CHEMICAL CORPORATION reassignment OCCIDENTAL CHEMICAL CORPORATION CHANGE OF NAME (SEE DOCUMENT FOR DETAILS). EFFECTIVE APRIL 1, 1982. Assignors: HOOKER CHEMICALS & PLASTICS CORP.
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/40—Esters thereof
    • C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having three nitrogen atoms as the only ring hetero atoms
    • C07F9/6521—Six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/51—Phosphorus bound to oxygen
    • C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
    • C08K5/5317—Phosphonic compounds, e.g. R—P(:O)(OR')2
    • C08K5/5333—Esters of phosphonic acids
    • C08K5/5353—Esters of phosphonic acids containing also nitrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/51—Phosphorus bound to oxygen
    • C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
    • C08K5/5317—Phosphonic compounds, e.g. R—P(:O)(OR')2
    • C08K5/5333—Esters of phosphonic acids
    • C08K5/5373—Esters of phosphonic acids containing heterocyclic rings not representing cyclic esters of phosphonic 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
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2913—Rod, strand, filament or fiber
    • Y10T428/2933—Coated or with bond, impregnation or core
    • Y10T428/2964—Artificial fiber or filament
    • Y10T428/2965—Cellulosic
    • 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
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2913—Rod, strand, filament or fiber
    • Y10T428/2933—Coated or with bond, impregnation or core
    • Y10T428/2964—Artificial fiber or filament
    • Y10T428/2967—Synthetic resin or polymer

Definitions

  • ABSTRACT New compounds are disclosed of the formula RCH when New NYN NHCHZR wherein R is independently selected from the group consisting of and wherein R is lower alkyl.
  • the compounds of this invention serve as flame retarding agents for textiles and as additives to render polymers and copolymers flame retardant.
  • Flame retardant textiles have been produced by depositing metal oxides, within or on the textile fibers, by the successive precipitation of ferric oxides and a mixture of tungstic acid and stannic oxide or by successive deposition of antimony trioxide and titanium dioxide.
  • Such processes require plural treatment baths in which strongly acidic solutions are employed thus posing the problem of possible textile degradation.
  • metal oxide coatings on textile materials create difficulties in subsequent dyeing processes which deleteriously affect the hand of the finished product.
  • Another process involves the use of a single processing bath wherein a dispersion of a chlorinated hydrocarbon and finely divided antimony oxide is padded on the textile material. Near the textile combustion temperature antimony oxide will react with hydrogen chloride.
  • thermoplastic and thermosetting resin compositions which are flame retardant is of considerable commercial importance.
  • articles as castings, moldings, foamed 0r laminated structures and the like are required, or are at least desired, to be resistant to fire and flame and to possess the ability to endure heat without deterioration.
  • the use of various materials incorporated into thermoplastic and thermosetting resins so as to improve the flame retardance thereof has ben known.
  • Many compounds have been commercially available for such use, among them being chlorostyrene copolymers, chlorinated paraffin wax in admixture with triphenyl styrene, chlorinated paraffins and aliphatic antimonical compounds, as well as antimony oxide-chlorinated hydrocarbon mixtures.
  • chlorostyrene copolymers chlorinated paraffin wax in admixture with triphenyl styrene
  • chlorinated paraffins and aliphatic antimonical compounds as well as antimony oxide-chlorinated hydrocarbon mixtures.
  • the present invention relates to a group of compounds which may be added to thermoplastic and thermosetting resins in relatively small amounts and still produce satisfactory flame retardant compositions which will not crystallize nor oil out of the resin after incorporation therein.
  • RcH -HN L HCH R consisting of mi and (R' oi and wherein R is lower alkyl.
  • novel compounds for imparting flame retardancy to textiles and thermoplastic and thermosetting resin materials, of the formula 0 N ⁇ n RCH -NH I 2 f NHCHZNOR NHCH R wherein R is independently selected from the group consisting of N H HO-CH -NH "f Wl"'NHCH -P(OCH CH CH CH CH CH).
  • R is independently selected from the group consisting of N H HO-CH -NH "f Wl"'NHCH -P(OCH CH CH CH CH CH CH CH
  • the synthesis of the compositions of the present invention is accomplished by reacting a N- hydroxymethylated melamine of the formula NHCH OH with a trialkyl phosphite of the formula (R'O) P R is as previously described in a suitable solvent, excess phosphite or neat Typically, the reaction occurs at elevated temperatures and is continued for about 1 to about 12 hours.
  • Temperatures are generally about 50 to about 160C. Preferably reaction is continued from about 3 to about 6 hours at a temperature of about to about C.
  • the solvent and other volatiles are thereafter stripped, or otherwise removed from the product.
  • Suitable solvents include alcohols, glymes, dimethyl formamide or mixtures of the previous solvents with aliphatic or aromatic hydrocarbons.
  • One or more of the novel compounds of this invention may be applied to textile materials by conventional finishing techniques such as by thermal induced pad curing so as to incorporate into the textile a flame retardant amount thereof.
  • the compounds of this invention have advantages over the flame retardant agents of the prior art in that they may be used on a variety of textile materials of different chemical composition, and they may be applied by a variety of methods. They may be applied to materials in either the fiber or fabric form to give flame retarding materials with minimum detectable physical changes in the quality or hand of the textile material.
  • the products of this invention may be applied to cellulosic materials in several ways to give a durable flame retardant treatment.
  • the products of this invention may be reacted with formaldehyde to give N- hydroxymethyl derivatives which can react with cellulosic materials in a known manner.
  • aqueous mixtures of the products with formaldehyde, urea, trimethylol melamine or other known cellulose crosslinking agents may be applied to a cellulose substrate with the aid of an acidic catalyst by a pad dry process.
  • a further method is to mix the invention with an acid catalyst in aqueous solution and apply directly.
  • Nhydroxymethyl derivative of the products of this invention prepared by the condensation of the products with formaldehyde, are mixed in an aqueous medium with trimethylol malamine and a Lewis acid catalyst such as NH Cl or Zn(NO -6H O.
  • the cellulosic material is immersed in an aqueous solution of the methylol derivative, trimethylol melamine, and Zn(NO -6H O and squeezed on a two roll padder to 7090% wet weight pick-up.
  • the material is dried at 220270F for 1-3 minutes and cured at 300370F for l6 minutes in a circulating air oven.
  • the samples are then washed in hot water and dried.
  • the finished samples have a flame retardant add-on of about 5 to about 40 percent and preferably about 10 to about 25% by weight.
  • the flame retardant agents of this invention may be applied to various textiles such as cellulosic material, proteinaceous materials and blends of cellulosic or proteinaceous materials and analogous man-made fibers.
  • cellulosic materials applicant intends to embrace cotton, rayon, paper, regenerated cellulose and cellulose derivatives which retain a cellulose backbone of at least one hydroxy substituent per repeating glucose unit.
  • proteinaceous material applicant intends to embrace those textile materials comprising the functional groups of proteins such as the various animal wools, hairs and furs.
  • the flame retardant compounds or additives of the invention may be incorporated into thermoplastic or thermosetting resin compositions by any known method. That is to say, the flame retardant additive may be added to the resin by milling the resin and the additive on, for example, a two-roll mill, or in a Banbury mixer etc., or it may be added by molding or extruding the additive and resin simultaneously, or by merely blending it with the resin in powder form and thereafter forming the desired article. Additionally, the flame-retardant may be added during the resin manufacture, i.e., during the polymerization procedure by which the resin is made, provided the catalysts etc. and other ingredients of the polymerization system are inert thereto.
  • the compounds of this invention may be incorporated into the thermoplastic and thermosetting resin in flame-retarding amounts, i.e. generally amounts ranging from about 5 percent by weight, to about 50 percent by weight, preferably from about percent by weight, to about 40 percent by weight, based on the weight of the polymer, have been found sufficient.
  • thermoplastic and thermosetting resins embraced within the scope of this invention include the homopolymers and copolymers of unsaturated aliphatic, alicyclic, and aromatic hydrocarbons. Suitable monomers are ethylene, propylene, butene, pentene, hexane, heptene, octene, 2-methylpropene-l, 3- methylbutenel, 4-methylpentene-l ,4-methyl-hexene- 1,5-methylhexenel bicyclo-( 2.2.1 )-2-heptene, butadiene, pentadiene, hexadiene, isoprene, 2,3-dimethylbutadiene-1,3 2-methylpentadienel ,3, 4- vinylcyclohexene, vinylcyclohexene, cyclopentadiene, styrene and methylstyrene, and the like.
  • polymers in addition to the above-described olefin polymers that are useful in the invention include polyindene, idenecoumarone resins; polymers of acrylate esters and polymers of methacrylate esters, acrylate and methacrylate resins such as ethyl acrylate, nbutyl methacrylate, isobutyl methacrylate, ethyl methacrylate and methyl methacrylate; alkyd resins and paint vehicles, such as bodied linseed oil; cellulose derivatives such as cellulose acetate, cellulose acetate butyrate, cellulose nitrate, ethyl cellulose, hydroxyethyl cellulose, methyl cellulose and sodium carboxymethyl cellulose; epoxy resins; furan resins (furfuryl alcohol or furfuralketone); hydrocarbon resins from petroleum; isobutylene resins (polyisobutylene); isocyanate resins (polyurethanes); melamine
  • the polymers of the invention can be in various physical forms, such as shaped articles, for example, moldings, sheets, rods, and the like; fibers, coatings, films and fabrics, and the like.
  • the compounds of this invention have been found to have particular utility in ABS resins and in elastomeric materials such as acrylic rubber; acrylonitrilebutadiene styrene terpolymers; butadieneacrylonitrile copolymers; butyl rubber; chlorinated rubbers, e.g., polyvinyl chloride resins, chloroprene rubber, chlorosulfonated polyethylene; ethylene polymers, e.g., ethylene-propylene copolymers, ethylene-propylene terpolymers; fluorinated rubbers, butadiene rubbers, e.g., styrene-butadiene rubber, isobutylene polymers, polybutadiene polymers, polyisobutylene rubbers, polyisoprene rubbers; polysulfide rubbers; silicon rubbers; urethane rubbers; high styrene resins latices, high styrene resins, vinyl resins;
  • ASTM Test D2863-70 used in accordance with the following examples, generally provides for the comparison of relative flammability of self-supporting plastics by measuring the minimum concentration of oxygen in a slowly rising mixture of oxygen and nitrogen that will support combustion.
  • the procedure encompasses supporting cylindrical test specimens -150 mm X 8.0 mm vertically in a glass tube fitted with controlled upward oxygen/nitrogen gas flow. The top of the specimen is ignited and oxygen flow is adjusted until it reaches that minimum rate which the specimen is extinguished before burning 3 minutes or 50 mm whichever happens first.
  • the oxygen index(n) is then calculated as follows:
  • O is the volumetric flow of oxygen, at the minimal rate and N is the corresponding volumetric flow rate of nitrogen.
  • a modification of ASTM Test D635-68 used in accordance with the following examples, generally provides for the comparison of burning rates, selfextinguishment and non-burning characteristics of plastics in the form of sheets, bars, plates or panels.
  • the procedure encompasses preparing 150-200 mm X 8 mm plastic samples with and without the subject flame retardant additive. Each sample is marked at points 1 inch and 4 inches from its end and held, marked end in the flame, at a 45 angle in a controlled burner flame (1 inch flame length) for two 30 second attempt. The movement of the flame up the length of the sample through the two points is measured for rate of burning, non-burning or self-extinguishing characteristics.
  • a sample is rated SE(self-extinguishing) if the flame burns through the first point but extinguishes before reaching the second point.
  • a sample is rated NB(nonburning) if, upon ignition it does not burn to the first point.
  • AATCC test method 34-1969 The Vertical Char Test, used in accordance with the following examples, generally provides for the comparison of relative flammability of 2% inch X 10 inch fabric test specimens when exposed to a controlled burner flame, under controlled conditions, for periods of 12.0 and 3.0 seconds. Charred specimens are thereafter subjected to controlled tearing tests, using tabulated weights, to determine the average tear length as representing the char length of the fabric. In addition, samples which are wholly consumed by the flame are rated (B) and samples which do not burn are rated (NB). For comparison purposes, it should be noted that untreated samples of the fabrics used in the examples of this case would be consumed for this test.
  • the fabric was then squeezed to 80 percent wet pickup on a laboratory padder, dried for about 2 minutes at about 250F and cured for about 4 minutes at about 350F in a circulating air oven.
  • the fabric was then washed with tide detergent, for one wash cycle in a standard, home type, automatic washer and tumble dried.
  • the thus treated and washed fabric was found to have an initial resin add-on of about 16.2 percent and when tested by AATCC method 34-1969, had an initial calculated char length of 5.5 inches.
  • EXAMPLE Xl A padding solution was prepared by the process of Example X utilizing tris-Ndimethylphosphonomethyl melamine. 5.0 ounce per square yard cotton fabric was padded through this above solution and thereafter treated and tested in accordance with Example X. The results of testing indicated an initial vertical char of 3.8 inches with a 4.9 inch vertical char after 10 wash cy cles.
  • EXAMPLE Xll A solution was prepared, as in Example X, to which was added 25g of a 50 percent methylolated melamine solution and 7.5g of Zn(NO '6H O.
  • the fabric was then dried at about 240F for about 2.5 minutes and cured at about 330F for about minutes in a circulating air oven.
  • the fabric was washed, with tide detergent in a standard home type automatic washer for one complete wash cycle and tumble dried.
  • the thus treated fabric was subjected to testing by AATCC method 34-1969 and had a calculated char length of 4.2 inches.
  • the treated and washed fabric was thereafter subjected to nine more wash cycles and, when tested by AATCC method 34-1969 had a calculated char length of 5.1 inches.
  • the fabric was squeezed to about 65 percent wet pick-up on a laboratory padder and cured for about 4 minutes at 350F in a circulating air oven. The fabric was then washed by rinsing with water for about 10 minutes and thereafter air dried. Resin add on was calculated to be about 10.7 percent by weight. This fabric was then subjected to testing under AATCC test method 34-1969 and had a calculated char length of 2.3 inches. The fabric was then subjected to four additional water wash cycles and tested by AATC test method 34-1969 to have a 2.5 inch char length.
  • the fabric was then subjected to AATCC test method 34-1969 and had a calculated char length of 3.3 inches.
  • the fabric was then subjected to 4 additional wash and dry cycles as above described and when subjected to testing had a char length of 3.5 inches.
  • EXAMPLE XVIII Rayon staple fiber was immersed in the padding solution of Example XVII, and thereafter squeezed on a laboratory padder to percent wet pick-up. The fiber was then dried in a circulating air oven at about 250F for about 5 minutes and cured at about 350F for about 10 minutes. The fabric was then washed by hand in running water for about 5 minutes and air dried. Untreated rayon staple fiber and the treated fiber were tested when ASTM test D2863-70 and found to have an oxygen index of 18.9 and 29.0 respectively. Both the untreated and treated rayon fiber were placed in a burner flame for 3 seconds.
  • the untreated fiber was 'r A a L e n Verucnl Cha (inches) Examplg Compound lnirial After l0 Hash CyzleS o o N a 5. ⁇ XII tocu cuy vcn nnf/ m nu CH P(0CH CH u IM-CH2-P(OCH2CH3)2 o o H N u 3 9 xlrr tocn rcn uu n-un cu M001 3 7 NH-CR2-P(0H3)2 2. 5.0 XIV noca ua-f T an cn New 9 NH-CHZ-V (04:11
  • said textile is selected from the group consisting of cellulosic fibers, proteinoceous fibers and blends thereof.
  • R is independently selected from the group 1.
  • N l 4 process for rendering thermosetting resin compositlons flame retardant which comprises applying to N R said resin about 5 to about percent by weight of a compound of the formula I NHCH NHCl-l R 2 2 l 8.
  • N R said resin about 5 to about percent by weight of a compound of the formula I NHCH NHCl-l R 2 2 l 8.
  • R is independently selected from the group the ula:
  • An article comprising a textile selected from the 2 N 2 2 3 )2 group consisting of cellulosic fibers, proteinaceous fihers and blends thereof and about 5 to about 50 P 9.
  • the article of claim 5 wherein the compound is of cent by weight of a compound of the formula the formua]:
  • R is independently selected from the group 12.
  • the article of claim 6 wherein the compound is consisting of OH and of the formula:

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Polymers & Plastics (AREA)
  • Medicinal Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Fireproofing Substances (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
US401767A 1972-03-30 1973-09-28 Method of rendering textiles flame retardant with phosphorus containing melamine Expired - Lifetime US3885912A (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
GB1390973A GB1429004A (en) 1972-03-30 1973-03-22 Phosphonate esters useful as fire retardant additives
DE2315212A DE2315212A1 (de) 1972-03-30 1973-03-27 Phosphor enthaltende, feuerhemmende zusatzstoffe
FR7310952A FR2178055A1 (cs) 1972-03-30 1973-03-27
CA167,355A CA1019756A (en) 1972-03-30 1973-03-28 Phosphorus containing fire retardant additives
BE129393A BE797473A (fr) 1972-03-30 1973-03-28 Adjuvants ignifugeants contenant du phosphore
JP48036574A JPS4915291A (cs) 1972-03-30 1973-03-30
NL7304498A NL7304498A (cs) 1972-03-30 1973-03-30
US401767A US3885912A (en) 1972-03-30 1973-09-28 Method of rendering textiles flame retardant with phosphorus containing melamine

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US23980072A 1972-03-30 1972-03-30
US23979772A 1972-03-30 1972-03-30
US401767A US3885912A (en) 1972-03-30 1973-09-28 Method of rendering textiles flame retardant with phosphorus containing melamine

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US3885912A true US3885912A (en) 1975-05-27

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US401767A Expired - Lifetime US3885912A (en) 1972-03-30 1973-09-28 Method of rendering textiles flame retardant with phosphorus containing melamine

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US (1) US3885912A (cs)
JP (1) JPS4915291A (cs)
BE (1) BE797473A (cs)
CA (1) CA1019756A (cs)
DE (1) DE2315212A1 (cs)
FR (1) FR2178055A1 (cs)
GB (1) GB1429004A (cs)
NL (1) NL7304498A (cs)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4020224A (en) * 1974-07-22 1977-04-26 Monsanto Research Corporation Flame retardant method
US4086206A (en) * 1976-07-05 1978-04-25 Sanko Kaihatsu Kagaku Kenkyosho Organophosphorus compounds and process for the production thereof
US4113795A (en) * 1977-07-05 1978-09-12 Asahi-Dow Limited Flame-retardant polyphenylene ether resin composition
US4461862A (en) * 1980-06-02 1984-07-24 Ludwig Eigenmann Self extinguishing polymeric compositions, which upon contacting a flame provide a nondropping char-forming incandescent crust, and which do not produce flame neither toxic fumes
US4606853A (en) * 1983-08-11 1986-08-19 Imperial Chemical Industries Plc Fire retardant polyamide compositions
US5610210A (en) * 1993-02-09 1997-03-11 Basf Aktiengesellschaft Aminovinylphosphonic ester stabilizers for organic material
US5948837A (en) * 1996-12-19 1999-09-07 Montell North America Inc. Process for the production of flame retarding additives for polymer compositions, and products obtained from said process
US20060053739A1 (en) * 2004-09-10 2006-03-16 Jaffee Alan M Methods of providing water protection to floor structures and floor structures formed by the same
US20100173084A1 (en) * 2002-11-29 2010-07-08 Andrea Piana Methods, Systems, and Compositions for Fire Retarding Substrates

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4299782A (en) * 1980-03-24 1981-11-10 Pennwalt Corporation Phosphorus derivatives of 1,3-diethanolurea
DE3933546A1 (de) * 1989-10-07 1991-04-11 Bayer Ag Neue aminomethanphosphonsaeurearylester, verfahren zu ihrer herstellung und ihre verwendung
DE3933549A1 (de) * 1989-10-07 1991-04-11 Bayer Ag Neue aminomethanphosphonsaeurearylester, verfahren zu ihrer herstellung und ihre verwendung

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2781281A (en) * 1955-05-23 1957-02-12 Ciba Ltd Flame-proofing of textiles
US3645936A (en) * 1969-05-09 1972-02-29 Courtaulds Ltd Flame-retardant regenerated cellulose filaments

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2781281A (en) * 1955-05-23 1957-02-12 Ciba Ltd Flame-proofing of textiles
US3645936A (en) * 1969-05-09 1972-02-29 Courtaulds Ltd Flame-retardant regenerated cellulose filaments

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4020224A (en) * 1974-07-22 1977-04-26 Monsanto Research Corporation Flame retardant method
US4086206A (en) * 1976-07-05 1978-04-25 Sanko Kaihatsu Kagaku Kenkyosho Organophosphorus compounds and process for the production thereof
US4113795A (en) * 1977-07-05 1978-09-12 Asahi-Dow Limited Flame-retardant polyphenylene ether resin composition
US4461862A (en) * 1980-06-02 1984-07-24 Ludwig Eigenmann Self extinguishing polymeric compositions, which upon contacting a flame provide a nondropping char-forming incandescent crust, and which do not produce flame neither toxic fumes
US4606853A (en) * 1983-08-11 1986-08-19 Imperial Chemical Industries Plc Fire retardant polyamide compositions
US5610210A (en) * 1993-02-09 1997-03-11 Basf Aktiengesellschaft Aminovinylphosphonic ester stabilizers for organic material
US5948837A (en) * 1996-12-19 1999-09-07 Montell North America Inc. Process for the production of flame retarding additives for polymer compositions, and products obtained from said process
US20100173084A1 (en) * 2002-11-29 2010-07-08 Andrea Piana Methods, Systems, and Compositions for Fire Retarding Substrates
US20060053739A1 (en) * 2004-09-10 2006-03-16 Jaffee Alan M Methods of providing water protection to floor structures and floor structures formed by the same

Also Published As

Publication number Publication date
FR2178055A1 (cs) 1973-11-09
CA1019756A (en) 1977-10-25
DE2315212A1 (de) 1973-10-11
NL7304498A (cs) 1973-10-02
BE797473A (fr) 1973-09-28
GB1429004A (en) 1976-03-24
JPS4915291A (cs) 1974-02-09

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