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United States Patent (19) 11 Patent Number: 5,788,915 Blount (45) Date of Patent: Aug

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United States Patent (19) 11 Patent Number: 5,788,915 Blount (45) Date of Patent: Aug IIIUSOO5788915A United States Patent (19) 11 Patent Number: 5,788,915 Blount (45) Date of Patent: Aug. 4, 1998 54 FLAME RETARDANT COMPOSITIONS 57 ABSTRACT UTILIZING PARTIALLY HYDROLYZED AMNO CONDENSATON COMPOUNDS Flame retardant compositions of this invention are produced by incorporating a partially index (LOI) hydrolyzed amino 76 Inventor: David H. Blount, 6728 Del Cerro condensation composition in a more flammable organic Blvd., San Diego, Calif. 92120 material. The partially hydrolyzed amino condensation com pounds are produced by heating urea or heating urea with (21) Appl. No.: 801,776 other nitrogen containing compounds that will condensate with or react with isocyanic acid and/or cyanic acid thereby 22 Filed: Feb. 14, 1997 producing an amino condensation compound which is then Related U.S. Application Data partially hydrolysis is done by reacting it with a limited amount of water. The partially hydrolyzed amino conden 62) Division of Ser. No. 723,779, Sep. 30, 1996. sation compounds may be used alone or may be mixed with or reacted with carbonization auxiliaries, aldehydes and (51) Int. Cl. ........................ C09K 21A00; C08G 12/12 fillers to produce a partially hydrolyzed amino condensation 52 U.S. Cl. ........................... 252/609; 528/259; 252/601 composition which is incorporated in more flammable 58) Field of Search ..................................... 252/609, 601: organic compositions such as polyurethanes, polyester 528/259 resins. epoxy resins, vinyl resins and other resins. The partially hydrolyzed amino condensation salts of 56 References Cited phosphorus, boron or sulfur containing compounds and the U.S. PATENT DOCUMENTS partially hydrolyzed amino condensation-aldehyde resins 3,900,665 8/1975 Weil ........................................ 428/.276 may also be used as the flame retardant compound in this 4,246,146 1/1981 Wood et al. ... 260/9 invention. For example, polyurethane foams can be rendered 4.385, 13 5/1983 Fracalossi et al. ... 52/55 less flammable with the partially hydrolyzed amino conden 5,34,928 5/1994 Verheist ............ 521/59 sation compounds or compositions and utilized as cushion 5,344,855 9/1994 Narita et al. 523/79 and insulating materials. 5,510,059 4/1996 Yuki et al. .............................. 252/.609 Primary Examiner-C. H. Kelly 30 Claims, No Drawings 5,788.915 1 2 FLAME RETARDANT COMPOSITIONS (A) urea; UT LIZING PARTIALLY HYDROLYZED (B) nitrogen containing compound that will condensate or AMNO CONDENSATION COMPOUNDS react with urea; then (C) water: This application is a divisional of Ser. No. 08/723.779 5 under conditions sufficient to prepare the partially hydro filed Sep. 30, 1996. lyzed amino condensation compounds (ammonium polyaminocarbamate). The urea is first heated to produce FIELD isocyanuric acid and/or cyanic acid then reacted with urea to The invention concerns urea being condensated with itself form biuret or a mixture of cyanuric acid and cymelide or or with other organic compounds with a plurality of nitrogen 10 reacted with Component B or with more urea plus Compo atoms such as amino compounds to produce amino conden nent B to produce a mixture of biuret, cyanuric acid and sation compounds which is then partially hydrolyzed. The cymelide and condensed urea-nitrogen containing com invention also concerns their preparation and use. The pound then they are partially hydrolyzed with a limit amount partially hydrolyzed amino condensation compounds are of water to produce ammonium polyaminocarbamate. useful to produce flame retardant plastics and to flame retard 15 In another aspect, the invention comprises partially natural products, and may be reacted with phosphorus hydrolyzed amino condensation salt of phosphorus and/or and/or boron containing compounds to produce other flame boron containing compound and a process to prepare a retardant compounds. The partially hydrolyzed amino con partially hydrolyzed amino condensation salt of a phospho densation compounds may also be reacted with aldehydes to rus and/or boron containing compound employing phospho produce partially hydrolyzed amino condensation-aldehyde rus and/or boron containing compound that will react with resins for use as molding compounds, as an adhesive, the partially hydrolyzed amino condensation compound coating resin or as a flame retardant compound. under conditions sufficient to prepare the partially hydro lyzed amino condensation salt of a phosphorus and/or boron BACKGROUND containing compound, and a process to prepare a partially The heating of urea to produce urea condensation 25 hydrolyzed amino condensation salts of a phosphorus and/or compounds, such as biuret and a mixture of cyanuric acid a boron containing compound comprising serially and cyamelide, is known in the arts, but the partially contacting, heating and reacting: hydrolysis of these compounds to produce improved flame (A) urea; retardant compounds is novel. The condensation of urea (B) nitrogen containing compound that will condensate or with other organic compounds with a plurality of nitrogen react with urea; then atoms and their partially hydrolysis is novel. The conden (C) water; then sation of isocyanuric acid and/or cyanic acid, (which are (D) phosphorus and/or boron containing compound that will produced by heating urea).with other nitrogen containing react with a partially hydrolyzed amino condensation compounds to produce flame retardant compounds is novel. compound. The partially hydrolyzed amino condensation compounds 35 component A and B are first heated and reacted, then a and their phosphorus and/or boron salts may be used as limited amount of water is added and heated to produce a flame retardant compounds in plastics and natural products. partially hydrolyzed amino condensation compound, then Urea and melamine were utilized as a flame retardant component D is added and reacted. compound by Fracalossi, et al., in U.S. Pat. No. 4.385,131. An addition aspect of this invention is the production of Melamine was utilized as flame retardant compounds in partially hydrolyzed amino condensation-aldehyde resins polyurethanes by Yukuta, et al... in U.S. Pat. No. 4,221,875 and a process to prepare partially hydrolyzed amino and by Grinbergs et al., in U.S. Pat. No. 4,745.133. Amino condensation-aldehyde resins under conditions sufficient to phosphates was utilized by Blount in U.S. Pat. No. 5.010, prepare the partially hydrolyzed amino condensation 113. aldehyde resin comprising serially contacting, heating and What is lacking and what is needed are useful inexpensive 45 reacting: partially hydrolyzed nitrogen containing organic compounds (A) urea; with a plurality of nitrogen moieties. The partially hydro (B) nitrogen containing compound that will condensate or lyzed amino condensation compounds and/or their salts of react with urea; then this invention and the partially hydrolyzed amino-aldehyde (C) water; then resins are novel flame retardant compounds. The partially 50 (E) aldehyde; and a hydrolyzed amino condensation compounds such as par (G) a basic or acidic catalyst; tially hydrolyzed urea condensation compounds, urea components A and B are first reacted to produce an amino melamine condensation compound, urea-dicyandiamide condensation compound which is then partially hydrolyzed compounds. urea-guanidine condensation compounds, etc. with a limit amount of water to produce a partially hydro are novel flame retardant compounds. What is additionally 55 lyzed amino condensation compound (ammonium lacking are compositions having such partially hydrolyzed polyaminocarbamate) which is then reacted with component amino condensation compounds and/or their salts employed E in the presence of component G. therein. An additional aspect of the invention is use of the partially hydrolyzed amino condensation compounds, partially SUMMARY hydrolyzed amino condensation salts of phosphorus and/or In one aspect, the invention comprises partially hydro boron compounds and partially hydrolyzed amino lyzed amino condensation compounds and their salts which condensation-aldehyde resins as flame retardant com Inamed ammonium polyaminocarbamate. Another aspect of pounds. The flame retardant use comprises contacting an the invention is a process to prepare partially hydrolyzed otherwise more flammable organic material with the par a mino condensation compound (ammonium 65 tially hydrolyzed amino condensation compounds and/or polyaminocarbamate) and/or their salts comprising serially partially hydrolyzed amino condensation salts of phospho contacting, heating and reacting: rus and/or boron containing compounds and/or partially 5,788,915 3 4 hydrolyzed amino condensation-aldehyde resins thereof nium carbonate, ammonium carbamate and urea in water. under conditions sufficient to lower the combustibility of the Most of the water is then removed under satisfactory physi otherwise more flammable organic material, for example cal conditions and by any satisfactory means such as plastics, natural products or polyurethanes. Thus, a further crystalization, distillation or air dried. Usually at ambient aspect of the invention is a flame-retardant composition temperature or at a temperature below the temperature that comprising an otherwise more flammable organic material ammonium carbamate breaks down into ammonia and car incorporated therewith a flame retardant amount of a par bon dioxide. The water is removed until there is about 10 to tially hydrolyzed amino condensation compound 40 parts by weight of water to 100 parts by weight
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