USOO5854309A United States Patent (19) 11 Patent Number: 5,854,309 Blount (45) Date of Patent: Dec. 29, 1998

54 FLAME RETARDANT COMPOSITIONS Primary Examiner Veronica P. Hoke UTILIZING AMNO CONDENSATION COMPOUNDS 57 ABSTRACT 76 Inventor: David H. Blount, 6728 Del Cerro Flame retardant compositions Such as polyurethane foams Blvd., San Diego, Calif. 92120 are produced by incorporating an amino condensation com position. The amino condensation compositions are pro 21 Appl. No.: 723,779 duced by heating urea or heating urea with other nitrogen containing compounds that will condensate with or react 22 Filed: Sep. 30, 1996 with isocyanic acid and/or cyanic acid or heating urea first (51) Int. Cl...... C09K 21/14 then reacting the condensation compounds with other nitro 52 U.S. Cl...... 523/179; 428/920; 428/921; gen containing compounds. The amino condensation com 521/83; 521/84.1; 521/94 pounds may be mixed with or reacted with carbonization 58 Field of Search ...... 428/920, 921; auxiliaries, aldehydes and fillers to produce an amino con 523/179; 525/428, 509, 517; 564/38, 45, densation composition which is incorporated in more flam 58, 59; 528/422, 423; 521/83, 84.1, 94 mable organic compositions Such as polyurethanes, polyes ter resins, epoxy resins, Vinyl resins and other resins. The 56) References Cited amino condensation Salts of phosphorus, boron or Sulfur U.S. PATENT DOCUMENTS containing compounds and the amino condensation aldehyde resins may also be used as the flame retardant 2,244,184 6/1941 Austin et al...... 525/517 compound in this invention. For example, polyurethane

3,629,052 12/1971 Knoepfler et al. ... 525/517 foams can be rendered less flammable with the amino 3,955.987 5/1976 Schaar et al...... 428/922 5,430,081 7/1995 Ohmae et al...... 524/436 condensation compounds or compositions and utilized as insulating materials. FOREIGN PATENT DOCUMENTS 4033705A1 4/1992 Germany. 4 Claims, No Drawings 5,854,309 1 2 FLAME RETARDANT COMPOSITIONS tions Sufficient to prepare the amino condensation Salt of a UTILIZING AMNO CONDENSATION phosphorus and/or boron containing compound, and a pro COMPOUNDS ceSS to prepare an amino condensation Salts of a phosphorus and/or a boron containing compound comprising Serially FIELD contacting (A) urea The invention concerns urea being condensated with other (B) nitrogen containing compound that will condensate or organic compounds with a plurality of nitrogen atoms Such react with urea as amino compounds to produce amino condensation com (E) phosphorus and/or boron containing compound that pounds. The invention also concerns their preparation and will react with an amino condensation compound. use. The amino condensation compounds are useful to An addition aspect of this invention is the production of produce flame retardant plastics and flame retard natural amino condensation-aldehyde resins and a process to pre products, and may be reacted with phosphorus and/or boron pare amino condensation-aldehyde resins under conditions containing compounds to produce other flame retardant Sufficient to prepare the amino condensation-aldehyde resin compounds. The amino condensation compounds may also 15 comprising Serially contacting be reacted with aldehydes to produce amino condensation (A) urea aldehyde resins for use as molding compounds or as a flame (B) nitrogen containing compound that will condensate or retardant compound. react with urea (F) aldehyde BACKGROUND (H) a basic or acidic catalyst The heating of urea to produce urea condensation An additional aspect of the invention is use of the amino compounds, Such as a mixture of cyanuric acid and condensation compounds as a flame retardant in the produc cyamelide, is known in the arts, but the use of these tion of amino condensation Salts of phosphorus and/or boron compounds as a flame retardant is novel. The condensation compounds and in the production of amino condensation of isocyanic acid and/or cyanic acid, (which are produced by 25 aldehyde resins. The flame retardant use comprises contact heating urea),with other nitrogen containing compounds to ing an otherwise more flammable organic material with the produce flame retardant compounds is novel. The amino amino condensation compounds and/or amino condensation condensation compounds and their phosphorus and/or boron Salts of phosphorus and/or boron containing compounds Salts are used as flame retardant compounds in plastics and and/or amino condensation-aldehyde resins thereof under natural products. Urea and melamine were utilized as a conditions sufficient to lower the combustibility of the flame retardant compound by FracaloSSi, et al., in U.S. Pat. otherwise more flammable organic material, for example No. 4,385,131. Melamine was utilized as flame retardant plastics, natural products or polyurethanes. Thus, a further compounds in polyurethanes by Yukuta, et al., in U.S. Pat. aspect of the invention is a flame-retardant composition No. 4,221,875 and by Grinbergs et al., in U. S. Pat. No. comprising an otherwise more flammable organic material 4,745,133. Amino phosphates was utilized by Blount in U.S. 35 incorporated there with a flame retardant amount of an amino Pat. No. 5,010,113. condensation compound and for a amino condensation Salt What is lacking and what is needed are useful inexpensive of a phosphorus and/or boron containing compound, and/or nitrogen containing organic compounds with a plurality of amino condensation-aldehyde resin, carbonization auxilia nitrogen moieties. The amino condensation compounds and/ ries and fillers. or their salts of this invention are novel flame retardant 40 The flame-retardant compounds of this invention are compounds. The amino condensation compounds Such as produced by heating urea (Component A) with a nitrogen urea condensation compounds, urea-melamine condensation containing compound (Component B) to above the melting compound, urea-dicyandiamide compounds, urea-guanidine point of urea to about 160 degree C. at ambient pressure for condensation compounds, etc., are novel flame retardant .1-3 hrs. Upon heating above the melting point urea form a compounds. What is additionally lacking are compositions 45 very reactive compound isocyanic acid which will react with having Such amino condensation compounds and/or their itself or other organic or inorganic nitrogen containing Salts employed therein. compounds especially amino compounds. In order to increase the flame retardant properties and carbonization SUMMARY properties of the amino condensation compound a carbon In one aspect, the invention comprises amino condensa 50 ization auxiliary (Component C), Such as, phosphorus acidic tion compounds and their Salts. Another aspect of the compounds, organic phosphorus compounds that will react invention is a process to prepare amino condensation com with an amino compound, boric acid, etc., is added to the pound and/or their Salts comprising Serially contacting melted amino condensation compound mixed and/or reacted. Other carbonization auxiliaries may be mixed with (A) urea 55 the amino condensation compounds to produce the flame (B) nitrogen containing compound that will condensate or retardant amino condensation composition. The amino con react with urea; densation compounds may be further reacted with an alde under conditions Sufficient to prepare the amino conden hyde (Component F) in the presence of a neutral or basic or sation compounds. The urea may be first reacted with acidic catalyst by mixing and heating the urea condensation itself then reacted with Component B or with more urea 60 compound with the aldehyde, usually in an aqueous plus Component B. medium, to just below the boiling point of the components In another aspect, the invention comprises amino conden at ambient or an elevated preSSure thereby producing a urea sation Salt of phosphorus and/or boron containing compound condensation-aldehyde resin. Fillers, (Component G) and and a process to prepare a amino condensation Salt of a carbonization auxiliaries may be added to the amino con phosphorus and/or boron containing compound employing 65 densation compounds or the amino condensation-aldehyde phosphorus and/or boron containing compound that will resin. The amino condensation compounds and amino react with the amino condensation compound under condi condensation-aldehyde resins with or without carbonization 5,854,309 3 4 auxiliaries and fillerS may be reacted with or added to or phoric acid, pyrophosphoric acid, triphosphoric acid, meta applied to a more flammable organic material (Component phosphoric acid, phosphorous acid, hydrophosphorous acid, D). phosphinic acid, phosphinous acid, phosphine oxide, phos phorus trihalides, phosphorus oxyhalides, phosphorus oxide, Component A mono-metal hydrogen phosphates, ammonia dihydrogen Urea is utilized as component A and may be in the form phosphate, bromated phosphates, alkali metal dihydrogen of a powder, crystals or a Solid. Any Suitable urea may be phosphate and halogenated phosphate-phosphite and their utilized that will react with a nitrogen containing compound. halides and acids. organic phosphorus compounds include, but not limited to, alkyl, cyclic, aryl and alkyl-aryl phos Component B phorus compounds, Such as, alkylchlorophosphines, alkyl phosphines, alkyl phosphites, dialkyl hydrogen phosphites, Any Suitable nitrogen containing compound that will react dialkyl alkyl phosphonates, trialkyl phosphites, organic acid with isocyanic acid and/or cyanic acid may be utilized in this phosphates, organic diphosphonate esters, aryl phosphites, invention. The nitrogen containing compound may be an aryl hydrogen phosphates, halogenated phosphonates esters organic or an inorganic compound. Suitable organic nitrogen 15 and mixtures thereof. Amino condensation borates may be containing compounds may be an aliphatic, aromatic, cyclic, produced by contacting boric acid and amino condensation aliphatic-aromatic or aliphatic-cyclic compound Such as, but compound under conditions Sufficient to prepare the amino not limited to, urea, urea derivatives for example, condensation borates which may also be utilized as a flame O-alkylureas, amino compounds, for example, melamine, retardant compound. Amino condensation boron-phosphates melamine cyanurate, dicyandiamide, biuret, guanidine, may be produced by contacting boron-phosphates and amino cyanoguanidine and aminoguanidine, ammonium carbonate, condensation compounds under conditions Sufficient to pre alkyl carbamates, alkyl isocyanates, polyisocyanates, Sul pare amino condensation boron-phosphate compounds famic acid, ammonium Sulfamate, amines, polyamines, which may also be utilized as a flame-retardant compound. thioureas, alkylanolamine, polyamides, amino hydrogen The Salt forming phosphorus containing compounds will phosphates, amidines, amides, aldimines, ketimines, guani 25 react with the amino condensation compounds to form an dine carbonate, amino carbonates, aminoborates, amino amino condensation Salt of a phosphorus containing com Sulfates, thiourea, thiourea derivatives, alkylanolamines, pound. nitriles, etc., and mixtures thereof. Suitable inorganic nitro gen containing compounds Such as, but not limited to, Component D ammonium phosphate, diammonium phosphate, ammonium Any Suitable organic material which is more flammable polyphosphate, ammonia borate, ammonium hydrogen than the amino condensation compounds, its Salts and amino Sulfate, quaternary ammonium Salts, ammonium condensation-aldehyde resin may be used in this invention. bicarbonate, ammonium carbonate, etc. and mixtures Any Suitable plastic resin composition or mixtures thereof thereof. The amino compounds are the preferred nitrogen and any Suitable natural organic material maybe used in this containing compound. The nitrogen containing compound 35 invention and mixtures thereof. These materials may be in may be utilized in the amount of 10 to 300 percent by weight the form of a Solid, cellular, Suspension, emulsion or Solu based on the weight of urea. tion. Suitable plastic resin include, but not limited to, vinyl dienes, vinyl-diene copolymers, polyesters, polyester resins, Component C phenoplasts, aminoplasts, polyepoxy resins, polyurethanes, Any Suitable carbonization auxiliaries may be utilized in 40 furans, polyamides, polyimides, polycarbonates, homopoly this invention. Suitable carbonization auxiliaries are com mers of Such olefins as ethylene, propylene, and butylene; pounds that in the presence of fire assist the formation of a block copolymers, consisting of optional combination of carbonization foam or char, Such as, additives that produce these olefins, polymers of vinyl compounds Such as Vinyl acidic components in the pyrolysis mixture, Such as phos chloride, acrylonitrile, methyl acrylates, Vinyl acetates and phorus acids, boric acids or Sulfuric acids. These acidic 45 Styrene; copolymers of the foregoing olefins with Vinyl components are compounds Such, for example, acids or monomers, copolymers and terpolymers of the foregoing Salts, or their derivatives of Sulfur, boron and phosphorus, olefins, with diene compounds, polyesterS Such as polyeth Such as, boron-phosphates, phosphates, and polyphosphates ylene terephthalate, polyester resins, polyamides Such as of ammonia, amines, polyamines, amino compounds, thio nylon; polycarbonates, polyoxymethylene, Silicones, ureas and alkyanolamines, but boric acid and its Salts and 50 polyethers, thioplasts, polyte trafluoroethylene, their derivatives, organic phosphorus compounds and their polysulfones, Vinyidienes, poly(Vinyl acetate), aliphaticallyl Salts, halogenated organic phosphorus compounds, their compounds, polyacrylonitrile, aliphatic die nes, Salts and their derivatives may also be used for this purpose. polybutadiene, butadiene-acrylonitrile, butadiene-Styrene The carbonization auxiliaries and other flame retardant copolymers, aromatic vinyl compounds, heterocyclic vinyl agents may be used in quantities of 0 to 300 percent by 55 compounds, cyclic unsaturated compounds, urethane-epoxy weight of the amino condensation compound. resins, polyimides, urethane Silicates, cellulose nitrate The nitrogen containing Salts of phosphorus acids are the rayon, regenerated cellulose film cellulose acetate, cellulose preferred carbonization compounds, Such as amino esters, cellulose ethers, cyanoethyl cellulose, chlorinated phosphate, amino Salts of organic phosphorus compounds rubber and mixtures thereof. and amino condensation Salt of inorganic and organic phos 60 Suitable natural products include but not limited to wood, phorus compounds. The amino condensation Salt of phoS cellulose, lignin-cellulose, paper, cotton, wool, linen, phorus compounds are produced by contacting the amino dammars, copols, other natural resins, rosins lignin, natural condensation compounds with a phosphorus containing rubber, natural proteins, e.g., Soya bean protein, Silk, glues, compound that will react with an amino compound, under gelatin, etc., modified cellulose and mixtures thereof. Natural conditions Sufficient to prepare an amino condensation Salt 65 organic material and plastics may be mixed together. The of a phosphorus containing compound. Suitable inorganic amino condensation compounds, its Salts and amino phosphorus compounds include, but not limited to, phoS condensation-aldehyde resin or amino condensation com 5,854,309 S 6 position maybe utilized in the amount of 10-200 percent, When four or more moles of urea are reacted with percentage based on the weight of the more flammable dicyandiamide a compound is formed that has the general organic material. formula of Component E Any Suitable basic or acidic catalyst may be used in the When four or more moles of urea are reacted with reaction of amino condensation compounds with aldehydes. guanidine a compound is formed that has the general for Suitable basic compounds include but not limited to, com mula of pounds containing alkali metal, alkaline earth metal and ammonia radicals and mixture thereof. Suitable acidic com pounds include, but not limited to, halogen acids, acidic When four of more moles of urea are reacted with phosphorus containing compounds, acidic compounds con aminoguanidine a compound is formed that has the general taining Sulfur, Sulphonic acid halides, carboxylic acids, formula of polycarboxylic acids, nitric acids and mixtures thereof. In Some reactions basic or acidic catalytic are not necessary. A 15 (NHCO). NHCO-HNCNHNH. catalytic amount is utilized. When four or more moles of urea are reacted with an alkyl Component F carbamate a compound is formed that has the general formula of Any suitable aldehyde may be reacted with the amino condensation compounds. Suitable aldehydes include, but (NHCO)-NHCO-NHCOOR not limited to, formaldehyde, paraformaldehyde, acetoaldehyde, butyraldehyde, chloral, and other alkyl wherein R is an alkyl radical. aldehydes, furfural, benzyl aldehyde and other aromatic Any amount of the amino condensation compound or the aldehydes and may be used in an amount up to 200 percent, amino condensation composition which includes the amino percentage based on the weight of urea. Aqueous formalde 25 condensation compound and/or its Salts and may include hyde is the preferred aldehyde. carbonization auxiliaries and fillerS Suitable for this inven tion may be utilized. Preferably, flame retardant amounts of Component G the amino condensation compounds and/or its Salts and/or the amino condensation-aldehyde resin or the amino con Any suitable filler may be used in this invention. The densation composition are from 10 percent by weight to fillers that may be utilized in the flame retardant mixture are about 200 percent by weight of the otherwise more flam usually insoluble in the reaction mixtures. They may be mable organic materials Such as polyester resins, polyepoxy inorganic Substances, Such as, alkali metal Silicates, alkaline resins, polyurethane components, acrylic and acrylate resins, earth metal Silicates, metal Silicates, Silica, metals, oxides, polyacrylonitrile, polystyrene, etc. carbonates, Sulphates, phosphates, borates, glass beads or 35 One method to measure this flame retardant capability is hollow glass beads. Hydrated aluminum oxide is preferred. an oxygen indeX test. By Selecting the various combinations They may be organic Substances, Such as, amino of the amino condensation composition to incorporate into a compounds, Such as urea, melamine, dicyandiamide, and more flammable organic material the average limiting oxy other cyanuric derivatives or their formaldehyde resins, gen index (LOI) can be raised 10 to 30 percent or more when aminophosphates, amino Salts of organic phosphates, 40 compared to otherwise comparable Samples without the phenol-aldehyde resin powder, powdered coke, graphite, flame retardant amino condensation composition. For graphite compounds, bituminous additives, Sawdust, carbo example three flexible polyurethane foams with the amino hydrates and mixtures thereof. The organic halide flame condensation composition were raised more than 30 percent retardant compounds may also be added as fillers. The filler to a LOI of 31.7, 30.3 and 30.7. may be used in the amount of 0 to 300 percentage based on 45 When the amino condensation composition were incor the weight of the amino condensation compound. porated into rigid polyurethane foam and tested with a propane torch with a %" flame held 1" from the foam for one ILLUSTRATIVE EMBODIMENTS minute, the flame did not spread, a char was formed, and the In general, the amino condensation compounds are com flame went out when the torch was removed. pounds which are produced by heating urea with other 50 Various amino condensation compositions were incorpo nitrogen containing compounds that will condensate or react rated into Solid resins, for example, flexible polyepoxy with urea to produce amino condensation compounds. The resins, rigid polyepoxy resins, polyester laminating and heated urea first form isocyanic acid and/or cyanic acid flexible resin, polystyrene resin, polymethyl methyl acrylate which polymerizes with itself to form a mixture of cyanuric resin, polyvinyl acetate resin, Solid polyurethane, acid and cyamelide and/or biuret. The urea condensation 55 polyisoprene, acrylonitrile, etc, then tested with a propane compound has the general formula of (NHCO). torch having a /2" flame, and held 1" from the sample for one When urea is heated with another nitrogen containing minute, the flame did not spread, and went out when the compound, Such as, melamine a different compound is flame was removed. The said above material were tested formed. When four or moles of urea are reacted with one without the amino condensation composition and all burned. mol of melamine a new compound is formed that has the 60 Various natural products Such as wood shingles, paper, general formula of cotton cloth, and cardboard were coated with various amino condensation compositions in an aqueous emulsion contain (NHCO)-NHCO-NH-CN(NH). ing 20% by weight of the powdered amino condensation When one mol of urea is heated with one mol of melamine composition then after the product had dried, they were 65 tested by applying a /2" flame from a propane torch to about a new compound is formed that has the general formula of 1" from the products, and the flame did not spread whereas NHCONHCN(NH). the uncoated products caught on fire and burned. 5,854,309 7 DESCRIPTION OF PREFERRED EXAMPLES The present invention will now be explained herein-after a) pyrophosphoric acid n) tris(2-chloropropyl) by way of a few examples and comparative examples, these b) phosphinic acid phosphate c) phosphorus trichloride O) triphenyl phosphite examples Setting, however, no limits to this invention. Parts d) phosphorus Oxytrichloride p) tris 2-chloroethyl phosphite and percentages are by weight, unless otherwise indicated. e) phosphorus Oxide q) triethyl phosphite f) ammonium dihydrogen r) urea dihydrogen phosphate EXAMPLE 1. phosphate s) diethyl phosphite g) mono-aluminum phosphate t) trimethyl phosphite 100 parts by weight of urea is heated to above the melting h) dimethyl methyl u) dibutyl pyrophosphoric acid point of urea and up to about 160 degree C. for 0.1 to 1 hour. 1O phosphonate (DMMP) v) melamine hydrogen i) dimethyl hydrogen boron-phosphate Ammonia evolves from the melted urea thereby producing phosphite X) hypophosphorous acid an amino condensation compound (urea condensation j) phenyl acid phosphate y) methyl amine salt of compound). The cooled amino condensation compound is k) methylchlorophosphine phosphoric acid ground into a fine powder. l) phosphorus z) O,O-dimethyl hydrogen 15 m) phosphorus thiochloride dithiophosphate EXAMPLE 2 100 parts by weight of urea and 50 parts by weight of melamine are mixed then heated to above the melting point EXAMPLE 8 of urea and up to 160 degree C. for .5 to 2 hours. Ammonia evolves from the mixture thereby producing an amino Example 1 is modified wherein a phosphorus containing condensation compound (urea-melamine condensation compound Selected from the list in example 7 is added to the compound). The cooled amino condensation compound is urea before it is heated thereby producing a mixture of urea ground into a fine powder. condensation Salt of a phosphorus containing compound and urea Salt of a phosphorus containing compound. The mixture EXAMPLE 3 25 is ground into a fine powder. Example 2 is modified wherein 75 parts by weight of EXAMPLE 9 melamine is used instead of 50 parts by weight. 30 parts by weight of the melted urea-melamine conden EXAMPLE 4 sation compound of example 2 are added to 100 parts by weight of a polypropylene triol with a 56 hydroxyl number Example 2 and 3 are modified wherein another nitrogen and a mol wt. of 3000 thereby producing a stable emulsion containing compound is used in place of melamine and for use in the production of flame retardant polyurethane Selected from the list below: products.

35 EXAMPLE 10 a) dicyandiamide k) biuret b) guanidine l) ammonium bicarbonate c) aminoguanidine m) methylolu rea Example 5 is modified wherein 20 parts by weight of d) thiourea n) methylthiocyanate powdered dimelamine phosphate is added to and mixed in e) ethylamine O) melamine phosphate with the melted urea condensation compound thereby pro f) diethylamine p) urea phosphate ducing a flame retardant amino condensation composition. g) ammonium carbonate q) melamine borate 40 h) urea carbonate r) guanidine carbonate EXAMPLE 11 i) diethylanolamine s) aniline i) ammonium sulfamate t) melamine cyanurate k) ethyl carbamate u) guanidine phosphate Example 3 is modified wherein 25 parts by weight of l) ethyl isocyanate V) acrylonitnie melamine powder are added to and mixed in with the melted 45 amino condensation compound thereby producing a flame retardant amino condensation composition. EXAMPLE 5 EXAMPLE 12 About 100 parts by weight of the urea-melamine conden 100 parts by weight of urea, 50 parts by weight of sation compound of example 2 is mixed with 25 parts by 50 melamine powder and 20 parts by weight of boric oxide are weight of phosphoric acid (75%) then heated to above the mixed then heated above the melting point of urea and up to melting point of the urea condensation compound for about 160 degree C. for 45 minutes while agitating. Ammonia 30 minutes there by producing a urea condensation Salt of evolves from the Solution, The urea-melamine condensation phosphoric acid. compound containing boric oxide is cooled, then ground 55 into a fine powder thereby producing a flame retardant EXAMPLE 6 amino condensation composition. Example 5 is modified by first reacting 5 parts by weight of boric acid with the 25 parts by weight of phosphoric acid EXAMPLE 13 thereby producing a boron-phosphate condensation com pound and utilizing it in place of the phosphoric acid in 60 100 parts by weight of urea, 30 parts by weight of example 5. dicyandiamide and 20 parts by weight of boric acid are mixed then heated above the melting point of urea and up to EXAMPLE 7 160 degree C. for .5 to 1 hour. Ammonia evolves from the mixture. The mixture of urea-dicyandiamide condensation Example 5 is modified wherein another phosphorus con 65 containing urea Salt of boric acid is cooled then grown into taining compound is utilized in place of phosphoric acid and a fine powder thereby producing a flame retardant amino Selected from the list below: condensation composition. 5,854,309 9 10 EXAMPLE 1.4 by weight of dimethyl methyl phosphonate (DMMP) thereby producing an amino condensation salt of DMMP 100 parts by weight of urea, 30 parts by weight of composition, then it was added and mixed with 60 parts by melamine phosphate are mixed then heated above the melt weight of a flexible polyepoxy resins with its polyamine ing point of urea and up to 160 degree C. for 40 minutes curing agent. The resin is cured then was tested with a /2" thereby producing a flame retardant amino condensation Salt propane flame held 1" away for sample for 1 minute. The of phosphate composition. After cooling it is ground into a flame did not spread and the flame went out when the torch fine powder. was removed. EXAMPLE 1.5 EXAMPLE 1.9 Example 12 is modified wherein 10 parts by weight of a 30 parts by weight of the amino condensation composi phosphorus Salt forming compound Selected from the list tion of example 10 are mixed with a flexible polyester resin below is added to and reacted with the amino condensation containing its catalyst. The resin is cured then flame tested composition; using a propane torch with a /2" flame held 1" form the 15 Sample for 1 minute. The flame did not spread and went out when the torch was removed. a) phosphoric acid h) phosphinic acid b) pyrophosphoric acid i) phosphorus Oxytrichloride EXAMPLE 2.0 c) dimethyl methyl i) ammonium dihydrogen phosphonate (DMMP) phosphate 30 parts by weight of the amino condensation composi d) dimethyl hydrogen phosphite k) dimethyl phosphoric acid tion of 17 c is incorporated into 70 parts by weight of a e) trimethyl phosphite l) diethyl ethyl phosphonate f) phenyl acid phosphate m) magnesium hydrogen flexible polyurethane foam produced from MDI and a triol g) phosphorus trichloride phosphate which weighs about 1.75 lbs./cu. ft. The foam was flame n) mono aluminum phosphate tested by using Calif. T133 Test wherein 100 gms of wood is burned on top of the foam. After burning the wood on the 25 foam there was a 50.5gms weight loss. A weight loSS of leSS EXAMPLE 16 than 60 gms is necessary to pass the test. Example 2 is modified wherein 20 parts by weight of a EXAMPLE 21 halogenated flame retardant compound Selected from the list 30 parts by weight of the amino condensation composi below is mixed with the powdered urea-melamine conden tion of example 10 are incorporated in a rigid polyurethane sation compound thereby producing a flame retardant amino foam of about 2 lbs./cu. ft., produced using polymeric MDI condensation composition: and polyol. The rigid polyurethane foam was flame tested a) brominated epoxy olgmer using a propane torch that had a %" flame and held 1" from b) decabromodiphenyl oxide the foam. The flame did not spread and went out when the c) pentabromodiphenyl oxide 35 torch was removed. d) 2,3-dibromopropanol e) octabromodiphenyl oxide EXAMPLE 22 f) tris (dichloropropyl) phosphite Example 14 is modified wherein another amino phospho g) tris(dichloropropyl) phosphite rus containing compounds is Selected from the list below 40 and utilized in place of melamine phosphate: EXAMPLE 1.7 Example 3 is modified wherein 20 parts by weight of a a) dimelamine phosphate 1) O-methyl urea powdered filler selected from the list below is mixed with b) dicyandiamide phosphate m) urea salt of boron-phosphate the powdered urea condensation compound thereby produc c) urea dihydrogen phosphate n) urea-formaldehyde phosphate 45 d) guanidine phosphate O) aminophenol phosphate ing a flame retardant amino condensation composition: e) aminoguanidine phosphate p) ammonium urea phosphate f) diethyltriamine urea q) ammonium melamine phosphate phosphate r) melamine salt of trimethyl a) hydrated aluminum O) urea phosphate g) melamine salt of dimethyl phosphite Oxide powder p) silica powder methyl phosphonate s) melamine salt of phenyl acid b) hydrated sodium q) phenol-formaldehyde 50 h) melamine salt of dimethyl phosphate silicate powder resin powder hydrogen phosphite c) melamine r) aluminum phosphate i) methylamine melamine d) dicyandiamide s) thiourea phosphoric acid e) urea t) hollow beads j) methyl carbamate salt of f) melamine phosphate u) expandable graphite phosphoric acid g) melamine borate v) melamine salt of DMMP 55 k) melamine salt of boron h) ammonium phosphate r) ammonium sulfate hydrogen phosphate i) ammonium pyrophosphate s) magnesium chloride i) ammonium carbonate t) antimony trioxide k) ammonium borate u) boron-phosphate powder l) ammonium sulfamate w) melamine boron-phosphate EXAMPLE 23 m) guanidine powder n) guanidine carbonate X) ammonium boron-phosphate 60 Example 1 is modified wherein the urea condensation powder compound is heated and reacted with 20 percent by weight of urea, percentage based on the weight of the urea conden sation compound. EXAMPLE 1.8 EXAMPLE 24 65 30 parts by weight of the urea-melamine condensation Example 4 is modified wherein the urea is first heated and compound of example 2 are mixed and reacted with 10 parts reacted with itself to form a urea condensation compound 5,854,309 11 12 then additional 20 percent by weight of urea, percentage amount sufficient to reduce the combustibility of the more based on the weight of the urea condensation compound, is flammable organic material, Said amino condensation com added with the nitrogen containing compound. position is produced by the proceSS comprising of mixing, I claim: heating and reacting the following components: 1. A method for reducing combustibility of a more flam 5 (A) urea mable organic material comprising incorporating an amino (B) nitrogen containing compound that will react with condensation composition with the more flammable organic isocyanic acid and/or cyanic acid produced by heating material, under reaction conditions of the more flammable urea, and Selected from the group consisting of organic material, and in an amount Sufficient to reduce the melamine, melamine cyanurate, dicyandiamide, combustibility of the more flammable organic material, Said guanidine, cyanoguanidine, aminoguanidine and mix amino condensation composition produced by the method tures thereof; in comprising of mixing, heating and reacting the following the amount of 10 to 300 percent by weight, percentage components, based on the weight of urea; then mixed with a (A) urea (C) filler in the amount of 300 percent by weight based on (B) nitrogen containing compound that will condensate 15 the weight of the amino condensation compound; and/or react with isocyanic acid and/or cyanic acid components A and B are first mixed then heated to above produced by heating urea, and Selected from the group the melting point of urea and up to 160 degree C. for consisting of melamine, melamine cyanurate, .1 to 3 hours at ambient or elevated pressure and dicyandiamide, guanidine, cyanoguanidine, ami reacted thereby producing an amino condensation com noguanidine and pound then mixed with component C. mixtures thereof; in the amount of 10 to 300 percent by 4. The flame retardant composition of claim 1 or claim 3 weight percentage based on the weight of urea; then wherein the filler is Selected from the group consisting of adding and mixing in a urea, melamine, dicyandiamide, melamine cyanurate, amino (C) Filler in the amount of 300 percent by weight based 25 phosphates, amino polyphosphates, aminoplasts, on the weight of the amino condensation compound: phenoplasts, powdered Synthetic resins, Sawdust, components A and B are first mixed, then heated to carbohydrates, bituminous additives, graphite, graphite above the melting point of urea and up to 160 degree compounds, cyanuric derivatives or their formaldehyde C. for .1 to 3 hours at ambient or elevated pressure resins, powdered coke, Silica, alkali metal Silicates, alkaline and reacted thereby producing an amino condensa earth metal Silicates, metals, metal Silicates, oxides, tion composition, then component C is added and carbonates, Sulphates, phosphates and borates, glass beads, mixed. hollow glass beads, hydrated aluminum oxide and mixtures 2. The product produced by the method of claim 1. thereof; in an amount of 300 percent by weight, percentage 3. A flame retardant composition produced by incorpo based on the weight of amino condensation compound. rating an amino condensation composition in a more flam mable organic material, under reaction conditions and in an