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United States Patent (19) 11 4,169,930 Blount 45) Oct United States Patent (19) 11 4,169,930 Blount 45) Oct. 2, 1979 (54) PROCESS FOR THE PRODUCTION OF 58 Field of Search ................. 260/448.2 N, 448.2 E; AMNO SILICATE COMPOUNDS AND 528/38 THER CONDENSATION PRODUCTS 76 Inventor: David H. Blount, 5450 Lea St., San 56) References Cited Diego, Calif. 92105 U.S. PATENT DOCUMENTS 21 Appl. No.: 786,617 4,011,253 3/1977 Blount ........................... 260/448.2 E 4,089,883 5/1978 Blount ....................... 260/448.2 E X (22) Filed: Apr. 8, 1977 Primary Examiner-Paul F. Shaver Related U.S. Application Data 57 ABSTRACT 60) Division of Ser. No. 652,338, Jan. 26, 1976, Pat. No. 4,033,935, which is a continuation-in-part of Ser. No. Silicic-amino compounds are formed by the chemical 559,313, Mar. 17, 1975, Pat. No. 3,979,362, which is a reaction of silicic acid with amino compounds in the continuation-in-part of Ser. No. 71,628, Sep. 11, 1970, presence of a suitable alkali at a suitably elevated tem abandoned. perature, and then by reacting the resultant compounds 51 Int. Cl’.............................................. C08G 77/04 with an aldehyde, a condensation product is formed. (52) U.S. C. .............................. 528/38; 260/448.2 N; 260/448.2 E 4 Claims, No Drawings 4,169,930 1. 2 PROCESS FOR THE PRODUCTION OF AMINO Reactions with other amino compounds are expected SILICATE COMPOUNDS AND THER to be similar to these, so that the mol ratios of the reac CONDENSATION PRODUCTS tants should be selected accordingly. Amino silicate compounds are theorized to react with CROSS-REFERENCE TO RELATED an aldehyde to form condensation products as follows: APPLICATIONS Urea silicate is theorized to react with formaldehyde This application is a division of U.S. Pat. application as follows: Ser. No. 652,338, filed Jan. 26, 1976, U.S. Pat. No. 4,033,938 which is a continuation-in-part of my copend 10 ing application, Ser. No. 559,313, filed Mar. 17, 1975 HO. SiO. NH CO. NH2 + H2CO - G U.S. Pat. No. 3,979,362, which is a continuation-in-part -CH of my earlier U.S. patent application, Ser. No. 71,628, CO CO filed Sept. 11, 1970, now abandoned. 15 HO. SiO. NH HO. SiO. NHU BACKGROUND OF THE INVENTION This invention relates in general to silicic acid com pounds and, more specifically, to a process for produc DETAILED DESCRIPTION OF THE ing novel silicic amino compounds and their condensa INVENTION tion products. 20 Any suitable amino compound may be used in my The silicic acid may be produced by any of the well novel process. Typical amino compounds include urea, known processes, such as chemically reacting a solution thiourea, melamine, quanidine, saccharin, propyl urea, of sodium metasilicate with a mineral acid to produce butyl urea, benzene and tolune sulfonamide, ammeline, silicic acid gel. Various silicic acids may be used, such 25 aliphatic diamines and other alkyl-substituted ureas. as silicic acid gel, orthosilicic acid, metasilicic acid, Various aldehydes may be used, such as formalde polysilicoformic acid, orthosilicoformic acid, silicofor hyde, acetaldehyde, butyaldehyde, chloral, acrolein, mic acid and monosilandiol. furfural and hexamethylene tetramine. The aldehyde Amino silicate compounds are useful as intermediates ratio may vary from 1:1 to 5:1 when reacting with an for the production of other compounds by further suit 30 amino silicate, depending on the methyl groups desired. able reactions. Typically, they may be used in the pro The chemical reaction between silicic acid and an duction of prepolymers, polymers, resins, as an additive amino compound may take place in a basic, neutral or or a reactant. Also, they may be used in coating agents, acidic pH, but it is enhanced by a basic pH. The chemi adhesives, impregnants, molding powder, paints, var cal reaction between an amino silicate and an aldehyde nishes, laminates, or their manufacture, and may be 35 may take place in a basic, neutral or acidic pH, but is reacted with other polymerizing compounds. enhanced by a basic or an acidic pH. The acidic cata The silicic-amino aldehyde condensation polymers lysts most commonly used are sodium hydrogen sulfate, are useful as coating agents, adhesives, impregnants, sulfuric acid, hydrochloric acid, formic acid, acetic molding powder, paints varnishes, laminates or their acid, and acid esters, such as acid alkyl phosphates. The manufacture, and may be reacted with other polymeriz most common basic catalyst is sodium carbonate, but ing compounds. other basic compounds may be used, such as calcium SUMMARY OF THE INVENTION hydroxide, sodium hydroxide, potassium carbonate, I have discovered that silicic acid will react chemi potassium hydroxide, ammonia and alkanolamine. The cally with an amino compound in the presence of a alkali may act as a catalyst directly, or it may react suitable alkali catalyst at a temperature just above the 45 slightly with one or the other of the primary reactants. melting point of the amino compound. The amino com From about 1 to 10 weight percent catalyst, based on pounds are basic and will react chemically with silicic the weight of silicic acid and amino compound used, acid without an alkali catalyst, but the reaction is en gives best results. hanced by a suitable alkali catalyst. The amino com The resin solutions of poly (aldehyde amino silicate) pound will react with silicic acid in the ratio of 1:1 mols 50 may be converted to a fully hardened state by pro or 2:1 mols. While the specific reaction which takes longed heating. Plasticizers may be used to improve place is not fully understood, typical reactions which flexibility and adhesiveness. Latent catalysts may be are believed to occur take place as follows: used to catalyze the final conversion of the molding Orthosilicic acid is theorized to react with urea as 55 powder from the initial stages of resin formation to the follows: infusible, insoluble product. An excess amount of silicic acid may be used as a filler. The amino silicate compounds may also from con densation products with acetones, furans, isocyanates, Metasilicic acid is theorized to react with urea as diisocyanates, epichlorohydrin, dicarboxylic acids and follows: anhydrides, silicones, and may be copolymerized with HO.SiO.OH-NH2CO.NH2-HO.SiO.NH unsaturated organic compounds. .CO.NH2+ H2O DESCRIPTION OF THE PREFERRED 65 EMBODIMENTS The following examples describe in detail certain preferred embodiments of the process of my invention. These preferred processes may, of course, be varied as 4, 169,930 3 4 described above with similar results. Parts and percent given off. Urea silicate is soluble in alkali hydroxide ages are by weight, unless otherwise indicated. solution, dilute sulfuric acid and other solvents. EXAMPLE I EXAMPLE IV Forty parts by weight of sodium silicate pentahydrate 5 One mol by weight of metasilicic acid and one mol by are added to 200 parts by weight of water, stirred until weight of urea are mixed, heated to 95 to 150° C. for 20 the sodium silicate goes into solution, then dilute sulfu to 60 minutes, until the reaction is substantially com ric acid is added until the pH is 4 to 6, thereby produc plete, thereby producing white granules of urea silicate. ing silicic acid gel. The silicic acid gel is washed and The said urea silicate is mixed into about one mol of filtered. The moist silicic acid gel is mixed with 20 parts 10 acetoaldehyde in an aqueous solution and the urea sili by weight of urea, heated to 90° to 150° C. for 20 to 60 cate goes into solution. The unreacted metasilicic acid is minutes, until the chemical reaction is substantially filtered out. About 15% to 25% of said metasilicic acid complete, at ambient pressure, thereby producing a is filtered out. The ureasilicate formaldehyde solution is white, granular compound, urea silicate (H2N.CO.NH heated to 70 to 110° C. for 20 to 60 minutes, until the SiO.OH). 15 desired viscosity is obtained, thereby producing poly The said urea silicate is mixed with an aqueous form (formaldehyde urea silicate) resin. The resin may be aldehyde solution in the ratio of 1:1 mols, heated to 70 produced as a thick clear resin or a solid, depending on to 100 C. while agitating, for 20 to 60 minutes, or until the length of time the resin is heated. the desired viscosity is reached, thereby producing poly (formaldehyde urea silicate) resin, which is clear in EXAMPLEV color and may be produced as a thick liquid or as a Clay is reacted with sulfuric acid, thereby producing solid. metasilicic acid, which is recovered by filtration. About The clear liquid of said resin may be used as an adhe one mol of said metasilicic acid is mixed with 2 mols of sive for wood and also may be used as a protective urea, heated to 90 to 150 C. for 20 to 30 minutes, coating for wood. The solid resin may be softened with 25 thereby producing white granules of diureasilicate. The heat and molded into useful objects. The said resin is said diurea silicate is added to an aqueous solution of soluble in acetic acid and may be used as a varnish or hexamethylene tetramine in the ratio of 1:1.5 mols, paint to protect wood; it leaves a tough, clear resin on heated to 70° to 110° C. for 20 to 90 minutes, thereby the wood when dry. producing a clear thick solution of poly (formaldehyde 30 diurea silicate) resin, and, upon further heating, a white EXAMPLE II resin is produced. The said white resin is soluble in Twenty-five parts by weight of silicic acid gel as acetic acid and produces a clear solution; the unreacted produced in Example I, that has been air dried at 25 to silicic acid is precipitated.
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