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UNITED STATES PATENT OFFICE 2,509,174 PROCESS of WATERPROOF NG TEXT LE Fabrics Milton J

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UNITED STATES PATENT OFFICE 2,509,174 PROCESS of WATERPROOF NG TEXT LE Fabrics Milton J Patented May 23, 1950 2,509,174 UNITED STATES PATENT OFFICE 2,509,174 PROCESS OF WATERPROOF NG TEXT LE FABRICs Milton J. Scott and Stuart H. Rider, Springfield, Mass, assignors to Monsanto Chemical Com pany, St. Louis, Mo., a corporation of Dela No Drawing. Application May 22, 1947, Serial No. 49,880 10 Claims. (C. 117-161) This invention relates to waterproofing con melamine containing about 2 mols of stearyl al positions and to materials treated therewith. cohol per mol of hexamethylol melamine. More particularly, the invention relates to cer tain aminotriazine-aldehyde-alcohol reaction Ecample I products and to cellulosic and proteinaceous ma 314 parts of spray dried crystalline hexa terials treated therewith. methylol melamine of Example I were mixed An object of this invention is to prepare water with 320 parts (10 mols) of anhydrous methanol proofing compositions. and 0.5 part of ethyl phosphoric acid. The mix A further object is to prepare aqueous emul ture was refluxed for 30 minutes at atmospheric sions of aminotriazine-aldehyde-alcohol reaction O pressure and then 404 (1.5 mols) parts of stearyl products. alcohol were added and refluxing continued for Another object is to provide waterproof coat 30 minutes. The solution was concentrated by S. vacuum distillation at about 25 inches of mercury Still another object is to provide Waterproof until the temperature rose to about 130 C. The textiles. S resulting material was a methyl stearyl ether of These and other objects are attained by pre hexamethylol melamine containing about 1.5 paring a liquid reaction product of an amino mols of stearyl alcohol per mol of hexamethylol triazine, an aldehyde, and two alcohols one of melamine. which is an aliphatic Saturated alcohol contain Eacample IV ing 6 carbon atoms or less and the other of which 20 Example III was repeated except that about is a saturated or unsaturated aliphatic alcohol 15 molls of cetyl alcohol were substituted for the containing at least 12 carbon atoms, and then steary alcohol. A methyl cetyl ether of hexa treating water-receptive materials with the liquid methylol melamine was obtained. reaction product to render then Water-repellent. In making the mixed ethers of alkylol amino The following examples are given in illustration 25 triazines, each of the components may be re and are not intended to limit the scope of this placed by analogous materials and the amounts invention. Where parts are mentioned, they are of the components may be varied Over a wide parts by Weight. range. ECarple Instead of melamine shown in Example I other 30 aminotriazines may be used. Typical examples 126 parts (1 mol) of melamine were mixed with of aminotriazines are: melamine, formoguana 480 parts of Formalin (equivalent to about 6 mois mine, melam, melem, aminotriazines in which 1 of formaldehyde). The pH of the mixture was or 2 amino groups are substituted by hydroxy, adjusted to about 8-9 and the mixture was then halogen, alkyl, aryl or aralkyl groups such as 2 refluxed at atmospheric pressure for 30 minutes. 35 hydroxy-4, 6-diamino-1,3,5-triazine, 2,4-dihy The resultant solution of hexamethylol melamine droxy-6-amino-1,3,5-triazine, 2 - chloro-4,6-di in water was cooled to crystallize the hexamethyl amino-1,3,5-triazine, 2-phenyl - 46 - diamino ol melamine thus producing an aqueous slurry. 1,3,5-triazine, 6-methyl-2,4-diamino - 13,5-tri The slurry was spray dried and the crystals were azine, aminotriazines in which the hydrogen recovered for further reaction. 40 atoms of the amino groups are partially Sub Eacample II stituted by amino, alkyl, aryl, or aralkyl groups such as 2,4,6-trihydrazino-1,3,5-triazine, mono-, 314 parts (about 1 mol) of spray dried crystal di-, or trialkyl melamines, e. g., 2,4,6-triethyl line hexamethylol melamine of Example I Were triamino-1,3,5-triazine, mono-, di-, or triaralkyl mixed with 504 parts (6 mols) of anhydrous n 45 melamines, mono-, di-, or triaryl melamines, e.g., butanol and 0.5 part of concentrated hydrochlo 2,4,6-triphenyl-triamino-1,3,5-triazine, etc. Mix ric acid. The mixture was refluxed for 30 mini tures of two or more of the above may also be utes at atmospheric pressure and then 538 parts employed. (2 mols) of stearyl alcohol were added and re The formaldehyde shown in Example I may be fluxing continued for 30 minutes at atmospheric 50 replaced in whole or in part by saturated or pressure to obtain a clear Solution. The Solu unsaturated aliphatic, allicyclic or aromatic al tion was concentrated by distillation at a vacuum dehydes. Typical examples of aldehydes which of 25 inches of mercury until a temperature of may be used are: formaldehyde, acetaldehyde, 130° C. Was obtained. The resulting material was propionaldehyde, butyraldehyde, hexaldehyde, a mixed steary n-butyl ether of hexamethylol SS octaldehyde, benzaldehyde, furfural, acrolein, 2,509,174 w 3 4. w methacrolein, crotonaldehyde, cinnamaldehyde, sufficient to activate the etherification reaction etc. For economic considerations, under present and does not interfere therewith. day conditions, the lower aliphatic aldehydes, The etherification catalysts include such acids especially formaldehyde, constitute a preferred as sulfuric, hydrochloric, acetic, phosphoric acids, class for use in making the resins of this inven etc. The acids are used in concentrated form tion. The aldehydes may be used in propor and contain a relatively minor percentage of tions ranging from 1 to 6 or more nois per mol of water. aminotriazine. The mixed alcohol ethers of alkylol aminotri The preliminary reaction to produce the al azines are liquid resins insoluble in Water and kylol aminotriazines as typified by Example I is soluble in organic solvents such as alcohols, ke carried out preferably under alkaline condi 0. tones, esters, toluene, benzene, mineral spirits, tions, i. e., a pH of 8-10 under refluxing conditions etc. They are water-white or slightly yellow in at atmospheric pressure. In the preferred emi color. They may be used to waterproof cellul bodiment of this invention the reaction under losic or proteinaceous materials such as paper, reflux is stopped by cooling as soon as a clear cotton, wood, wool, silk, viscose and cellulose Solution is obtained. The alkylol aninotriazine acetate rayons, etc. is then crystallized and freed from water and The liquid resins may be cured to an insolu excess aldehyde. It is, however, within the SCOpe ble, infusible state by the application of heat at of this invention to add the alcohols and etherifi about 100 to about 300° C. for a short period with cation catalysts to the Water solution of the out the addition of a curing catalyst. Acid cur alkylol melanine and then carrying out the eth ing catalysts may be used, if desired. erification step in an aqueous medium. The mixed ethers may be applied as a water In the second step of this invention, as illus proofing composition from a solution in organic trated in xamples II, III and IV, the n-butanol solvents or from an aqueous emulsion. and methanol may be replaced in whole or in part by other saturated aliphatic alcohols con Eacample W taining 6 carbon atoms or less, e. g., ethanol, 70 parts of a butyl-stearyl ether of hexameth propanol, isopropanol, isobutanol, pentanols, hex yol melamine made as shown in Example II arols, etc. To obtain the best results, the lower were dissolved in 30 parts of mineral spirits and alcohol should be a straight chain alcohol but then emulsified with 100 parts of Water in the branched chain alcohols such as isopropanol or presence of ammonium oleate as emulsifying isobutanol may be used to obtain specific prop agent. The resulting emulsion was an oil-in erties in the final resin. The amount of satu water type emulsion containing 36% solids by rated aliphatic alcohol to be used will depend on weight and 15% solvent by Weight. the process used and the product desired. From A portion of the emulsion was diluted with i to 6 mols of alcohol are used in the reaction water to about 10%. Solids (liquid resin) by with the alkylol aminotriazine and it is conven weight. Cotton cloth was drawn through the di ient to use a substantial excess of alcohol to act ute emulsion, partially dried by wringing and as a solvent for the resins produced. An excess then dried for a few minutes at approximately of alcohol is particularly desirable if the sub 100° C. followed by treatment for about 20 min stantially anhydrous process shown in Examples 40 utes at 145-155° C. The resin pick-up was found III and IV is used. If desired, the solvent may to be between 3 and 4%. The treated cloth had be removed by vacuum distiliation to obtain the substantially 100% resistance to water as meas pure liquid resin. ured by ASTM Test Method D583 40T using the . The stearyland cetyl alcohols shown in Exam Water Absorption (Spray) Method. After re ples II, III and W may be replaced in whole peated launderings with soap and hot water, a or in part by other saturated or unsaturated sample of the treated cloth still had excellent aliphatic alcohols containing at least 12 car water repellence and had not shrunk materially. bon atoms and preferably not more thari 35 car Moreover, repeated treatment with dry cleaning bon atoms, e. g., carnaubyl alcohol, heptadec solvents did not appreciably alter the water re ano, nondecanol, eicosanol, melissic alcohol, pellency of the treated fabric. etc. The long chain alcohols which may be A further portion of the emulsion made ac either straight or branched chain compounds, cording to Example W and diluted to about 10% may be used in proportions ranging from 1 to 4 solids with water was used to treat a Woolen mols of alcohol per mol of alkylol aminotriazine.
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