Patent GB-726661-A (GB)
Title: Manufacture of etherified condensation products of formaldehyde with amino-1:3:5-triazines containing at least two amino-groups
IPC: C08G12/42
Filed: 1951-11-29
Abstract: A polyamino - 1,3,5 - triazine/formaldehyde condensate containing per NH2-group at least one methylol group etherified with a higher monohydric alcohol containing at least 5 carbon atoms is made by re-etherifying with such an alcohol an aminotriazine/formaldehyde condensate containing per NH2-group at least one methylol group etherified with a lower monohydric alcohol containing at most 4 carbon atoms; the p  re-etherification is conducted at an elevated temperature under practically anhydrous conditions until at least one mol. of the lower alcohol per NH2-group is split off and substantially removed from the reaction mixture.  The catalyst is also eliminated from the mixture, e.g. by distillation or neutralization, followed by filtration to remove precipitating salt. Re-etherification is normally performed at 100-160 DEG  C., if desired under slightly reduced pressure and at the end of the reaction excess higher alcohol is removed, e.g. by washing or extraction with a solvent or by distillation, if desired under reduced pressure.  Specified amino triazines are melamine, N-phenyl melamine, benzoguanamine, acetoguanamine, ammeline and 2,4 - diamino - 6 - chloro - 1,3,5 - triazine.  Specified higher alcohols are myricyl, ceryl, stearyl, cetyl, lauryl, octyl, hexyl, amyl, oleyl, linoleyl and linolenyl alcohol; cyclohexanol, methyl-cyclohexanol, benzyl alcohol, abietinol, terpineol, menthol, borneol, phenylethyl alcohol, cinnamyl alcohol and furfuryl alcohol; alcohols obtained by reducing oxidized paraffin wax fatty acid; alcohols obtained by synthesis from carbon monoxide and hydrogen, alcohols obtained by reducing drying, semi-drying or non-drying oils with sodium and alcohol, suitable oils being linseed, soya bean, hemp, poppy seed, wood, dehydrogenated castor, cotton seed, coconut, cod liver, whale, menhaden, sperm and shark liver oil; alcohols obtainable from tall oil; and mixtures of fatty acid alcohols and abietinol.  Specified acid catalysts are hydrochloric, sulphuric, phosphoric, hypophosphorous, phthalic, maleic, chloracetic and formic acid; and Friedel-Crafts catalysts.  The products may be used as binding agents, e.g. for salves or waxes and those prepared from higher unsaturated alcohols may be used for lacquers after the addition of a drier.  They are soluble in esters, ketones, higher alcohols and aromatic and aliphatic hydrocarbons and are compatible with fatty oils, styrenated oils, colophony, copals, colophony - phenol resins, phenol - aldehyde resins, alkyd resins derived from maleic acid, urea and aminotriazine resins, vinyl resins and resins containing epoxide groups.  In examples (1) and (3)-(6), a methoxy methyl melamine is re-etherified with stearyl alcohol, linoleyl alcohol, soya bean alcohol, abietinol or a mixture of linoleyl alcohol and abietinol; (2) a butoxy methyl melamine is re-etherified with stearyl alcohol; (7) and (8) a methoxy methyl acetoguanamine or methoxy methyl benzoguanamine is re-etherified with linoleyl alcohol; (9) a methoxy methyl melamine is re-etherified with amyl alcohol, sec.-octanol, furfuryl alcohol, benzyl alcohol, lauryl alcohol, an alcohol obtained by reducing dehydrated castor oil, wood oil alcohol, methyl cyclohexanol, stearyl alcohol, linoleyl alcohol, poppy seed oil alcohol or hemp oil alcohol.