Patent GB-968501-A (GB)
Title: Melamine derivatives
IPC: C08F20/60
Filed: 1963-02-05
Abstract: The invention comprises acyl melamines of the formula: <FORM:0968501/C1/1> wherein each of R1, R2, R3, R4 and R5 independently represent a saturated or unsaturated aliphatic radical, a cycloaliphatic, araliphatic, aromatic or heterocyclic radical, or each of the pairs R2 and R3 and/or R4 and R5 together with the amino nitrogen atom and optional further hetero atoms represents a heterocycle, R1 may additionally represent hydrogen and R6 represents hydrogen or an alkyl radical.  The acyl melamines are prepared by reacting a melamine of the formula: <FORM:0968501/C1/2> with an acylating agent of the formula: <FORM:0968501/C1/3> wherein Y represents a halogen atom or a radical of the formula: <FORM:0968501/C1/4> The examples describe the preparation of compounds in which R1 represents hydrogen, R1 to R5 represent methyl, ethyl, propyl, isopropyl, butyl, octadecyl, dodecyl, beta-cyanoethyl, beta-methoxypropyl, gamma-methoxypropyl, allyl, cyclohexyl, phenyl, ortho-tolyl, meta-trifluoromethylphenyl and benzyl, and R2 and R3 and/or R4 and R5 complete a piperidine or morpholine ring.  The acyl melamines may be used to form polymers and copolymers.  2 - Methylamino - 4, 6 - bis - N - morpholino-1, 3, 5 - triazine is prepared by reacting one mol of cyanuric chloride with 2 mols of morpholine and one mol of methylamine.ALSO:Acyl melamines of the formula: <FORM:0968501/C3/1> wherein each of R1, R2, R3, R4 and R5\t independently represent a saturated or unsaturated aliphatic radical, a cycloaliphatic, araliphatic, aromatic or heterocyclic radical or each of the pairs R2 and R3 and/or R4 and R5 together with the amino nitrogen atom and optional further hetero atoms represents a heterocycle, R1 may additionally represent hydrogen and R6 represents hydrogen or an alkyl radical, are polymerized in bulk, solution, suspension or emulsion, alone or in the presence of one or more compounds containing at least one -HN=CH- and/or CH2=CH- group capable of addition by means of heat or light and in the presence or absence of polymerization catalysts.  Specified co-monomers are allyl, methallyl, crotyl, 1-chloroallyl, 2-chloroallyl, cinnamyl, vinyl, methylvinyl, 1-phenylallyl and butenyl esters of formic, acetic, propionic, butyric, valeric, caproic, stearic, acrylic, a - methylacrylic, a -ethylacrylic, a -propylacrylic, a -phenylacrylic, a -acyloxyacrylic, a -chloroacrylic, a -chlorocrotonic, oxalic, malonic, succinic, glutaric, adipic, azelaic, sebacic, fumaric, citraconic, mesaconic, itaconic, aconitic, benzoic, hexahydrobenzoic, phenylacetic, phthalic, hexahydrophthalic, terephthalic, benzoylphthalic, butyl sulphonic, para.-toluene sulphonic and cyanuric acids; methyl, ethyl, propyl, isopropyl, butyl, sec. butyl, 1,1-dihydroperfluorobutyl, amyl, stearyl and nonyl esters of acrylic, methacrylic and phenylacrylic acids; styrene; ortho-, meta- and para-chlorostyrene, -bromostyrene, -fluorostyrene, -methylstyrene, -ethylstyrene and -cyanostyrene; di-, tri- and tetra-chlorostyrenes, -bromostyrenes, -fluorostyrenes, -methylstyrenes, -ethylstyrenes and - cyanostyrenes; allylcyanostyrenes; a -methylstyrene, a -methyl-para.-methylstyrene; vinylnaphthalenes, vinylcyclohexanes, vinylfurans, vinylpyridines, divinylbenzenes, N-vinylcarbazoles, N-vinylpyrrolidiones; ethyl vinyl ether, dially, ether, ethyl methallyl ether; N-vinyl-caprolactam, N-allylcarolactam; acrylamide, methacrylamide, ethacrylamide; N-acryloyl piperidine, N-b -pyrrolidinoethylacrylamide, N-q -diethylaminopropyl methacrylamide, N-vinyl-N1-methylacetamide; N-vinylphthalimide, N-vinylsuccinimide; N-vinyl-N1-ethylurea; N-vinyl urethanes; acrylonitrile, methacrylonitrile, ethylacrylonitrile, phenylacrylonitrile; methylvinyl ketone, methylallyl ketone; methylvinyl sulphoxide; methylene malonic acid methyl and ethyl esters; ethylene, propylene, 1,3-butadiene, isoprene, 2-chlorobutadiene; vinylene carbonate; glycide acrylate, -methacrylate, -itaconate and -allylphthalate; vinyl fluoride, vinyl chloride, vinyl bromide, vinyl-iodide; vinylidene chloride, vinylidine fluoride, vinylidene iodide, vinylidene cyanide; tetrafluoroethylene, chlorotrifluoroethylene; triethoxy vinyl silicane, trimethyl vinyl silicane and diethylvinyl phosphate. Two acyl melamines of the above formula may also be copolymerized with each other.  Specified catalysts are hydrogen peroxide, barium peroxide, magnesium peroxide; ammonium, sodium and potassium persulphates (e.g. potassium peroxydisulphate), percarbonates, perborates and perphosphates; diethyl, dipropyl, dilauryl, dioleyl, distearyl, di-tert.butyl and di-tert.amylperoxides; tert. butyl hydrogen peroxides, tert. amyl hydrogen peroxide; diacetyl, dipropionyl, dilauroyl, dibenzoyl, succinyl and phthaloyl peroxides, coconut oil fatty acid peroxides, acetylbenzoyl peroxide, propionylbenzoyl peroxide; terpene peroxides (e.g. ascaridol); triphenylmethyl azobenzene, 1-azo-bis-1-phenylethane, 1-azo-bis-1-para-methoxyphenylethane, 1-azo-bis-1-para-chlorophenylethane, 2-azo-isobutyronitrile, 2-azo-isobutyric acid dimethyl and diethyl esters, para,para1-dinitro-diphenyl-azo-sulphone, potassium-azo-disulphonate; borotrifluorodiethyl ether complexes; concentrated sulphuric acid; lithium hydride, tetraethyl lithium aluminium, ethyl sodium, butyl lithium, ethyl magnesium bromide and naphthyl sodium.  Redox systems such as K2S2O8+NaHSO3 may also be used. Polyvinyl alcohol may be used as a suspension stabilizing agent.  The sodium salt of sulphosuccinic acid dioctyl ester may be used as an emulsifier.  Specified solvents are benzene, ethylbenzene, toluene, xylene, ethylene dichloride, chlorobenzene, dibutyl ether, butyl acetate, methyl ethyl ketone, tert.-butanol, tert.amyl alcohol, tert. hexyl alcohol, butanol, ethylene glycol monomethyl ether and water.  The acyl melamine polymers may be formed into films, moulded articles or coating masses, or may be used for binding layers of safety-glass, as adhesives and for impregnating paper.