Patent GB-1049463-A (GB)
Title: New hydroxyaryl-1,3,5-triazines, process for their preparation and their use
IPC: D21H21/14
Filed: 1964-02-13
Abstract: Ultra-violet light screening agents of the general formula <FORM:1049463/C4-C5/1> wherein U1 represents a hydrogen atom or an alkyl group with up to 4 carbon atoms, U2, U3 and U4 are identical or different and each represents a hydrogen atom, an alkyl group with up to 8 carbon atoms or a phenyl group, X represents -O- or -S-, and Z1 represents a hydrogen atom, an alkyl group with up to 4 carbon atoms, a hydroxyl group or an etherified hydroxyl group, may be incorporated in dyed or undyed soaps.ALSO:Ultra-violet light screening agents of the general formula <FORM:1049463/C6-C7/1> wherein U1 represents a hydrogen atom or an alkyl group with up to 4 carbon atoms, U2, U3 and U4 are identical or different and each represents a hydrogen atom, an alkyl group with up to 8 carbon atoms or a phenyl group, X represents -O- or -S-, and Z represents a hydrogen atom, an alkyl group with up to 4 carbon atoms, a hydroxyl group or an etherified hydroxyl group, may be used to protect pelts or hides and leathers made therefrom by material or chemical tanning.ALSO:The invention comprises compounds of the general formula <FORM:1049463/C2/1> wherein U1 represents a hydrogen atom or an alkyl group with up to 4 carbon atoms, U2, U3 and U4 are identical or different and each represents a hydrogen atom, an alkyl group with up to 8 carbon atoms or a phenyl group, X represents -O- or -S-, and Z1 represents a hydrogen atom, an alkyl group with up to 4 carbon atoms, a hydroxyl group or an etherified hydroxyl group. The compounds may be prepared by reaction of a compound of the general formula <FORM:1049463/C2/2> wherein U2, U3, U4 and X are as defined above, with an appropriate compound of the benzene series which contains in vicinal position to the resulting bond to the triazine ring a possibly etherified hydroxyl group, the reaction being conducted in an anhydrous medium in the presence of a Friedel-Crafts catalyst, particularly aluminium chloride.  When the starting material of the benzene series contains an etherified hydroxyl group in vicinal position to the resulting bond the reaction is accompanied by splitting of the etherified hydroxyl group to give a phenol group in the ortho position.  Compounds of the invention containing an etherified hydroxyl group in the para position to the bond to the triazine ring may also be obtained by etherifying the corresponding compound bearing a free hydroxy group in that position. The dihalotriazine starting materials of formula B above may be obtained according to the reaction scheme <FORM:1049463/C2/3> wherein A denotes an unsubstituted or substituted furan or thiophene residue as described above.  Examples are given.ALSO:Ultra-violet light screening agents of the general formula <FORM:1049463/C3/1> wherein U1 represents a hydrogen atom or an alkyl group with up to 4 carbon atoms, U2, U3 and U4 are identical or different and each represents a hydrogen atom, an alkyl group with up to 8 carbon atoms or a phenyl group, X represents -O- or -S-, and Z1 represents a hydrogen atom, an alkyl group with up to 4 carbon atoms, a hydroxyl group or an etherified hydroxyl group, may be incorporated in synthetic resins such as epoxy resins, polyester resins, vinyl resins, polystyrene resins, alkyd resins and aldehyde resins such as formaldehyde condensation products with phenol, urea or melamine. Examples describe (10) polyamide filament, (11) polyvinyl chloride foil, (14) polyethylene foil, and (15) polypropylene foil, containing compounds of the above general formula.ALSO:Ultra-violet light screening agents of the general formula <FORM:1049463/A5-A6/1> wherein U1 represents a hydrogen atom or an alkyl group with up to 4 carbon atoms, U2, U3 and U4 are identical or different and each represents a hydrogen atom, an alkyl group with up to 8 carbon atoms or a phenyl group, X represents -O- or -S-, and Z1 represents a hydrogen atom, an alkyl group with up to 4 carbon atoms, a hydroxyl group or an etherified hydroxyl group, may be incorporated in cosmetic preparations such as perfumes, dyed or undyed soaps and bath salts, skim and face creams, powders, insect repellents and sunburn oils and creams.ALSO:Ultra-violet light screening agents of the general formula <FORM:1049463/D1-D2/1> wherein U1 represents a hydrogen atom or an alkyl group with up to 4 carbon atoms, U2, U3 and U4 are identical or different and each represents a hydrogen atom, an alkyl group with up to 8 carbon atoms or a phenyl group, X represents -O- or -S-, and Z1 represents a hydrogen atom, an alkyl group with up to 4 carbon atoms, a hydroxyl group or an etherified hydroxyl group, may be used to protect textile materials and other fibrous nontextile materials.  The textile materials may be in the form of fibres, filaments, yarns, woven or knitted fabrics or as felt; the materials may consist of natural materials of animal origin such as wool or silk, of vegetable origin such as cotton, hemp, flax, linen, jute or ramie, of semi-synthetic materials such as regenerated cellulose, for example rayon or viscous including spun rayon, or of synthetic materials available by polymerisation or copolymerisation, such as polyacrylonitrile, polyvinyl chloride, polyethylene or polypropylene, or by poly-condensation, such as polyesters and polyamides.  The non-textile fibrous materials include paper, cardboard and paper pulps used in the manufacture of paper.  In Example 12, a bath containing a compound of the above general formula, aqueous ethanolic sodium hydroxide and an adduct of ethylene oxide with stearyl alcohol is neutralised with sulphuric acid; a polyamide fabric is immersed in the resulting dispersion, the mixture boiled and the fabric removed, rinsed and dried.