Patent GB-788747-A (GB)
Title: New dihydric phenols and resinous products prepared therefrom
Filed: 1955-05-20
Abstract: The invention comprises phenols of the formula: <FORM:0788747/IV (b)/1> R and R1 being hydrogen or alkyl of 1-4 carbon atoms, and R11 and R111 being alkyl of 1-4 carbon atoms.  They are made by sulphonation followed by alkali fusion from compounds of the formula: <FORM:0788747/IV (b)/2> which are themselves made by dimerisation of compounds of the formula: <FORM:0788747/IV (b)/3> and this last step is illustrated by (1) the dimerisation in toluene with sulphuric acid of a ,p-dimethylstyrene, a  - ethyl - p - methylstyrene, and a -m-dimethylstyrene, to give 1 - (4-methylphenyl) - 1,3,3,6 - tetramethyl - indane, 1 - (4 - methylphenyl) - 1,3 - diethyl - 3,6 - dimethyl indane, and 1-(3-methylphenyl)-1,3,3,5-tetramethyl-indane respectively; (2) the dimerization in toluene with aluminium chloride of crude, i.e. undistilled a -p-dimethylstyrene to give 1 - (4 - methylphenyl) - 1,3,3,6 - tetramethyl-indane, and of the same body distilled with p-toluene sulphonic acid.  In examples, the following are sulphonated with fuming sulphuric acid and the disulphonic acids obtained are fused with sodium or potassium hydroxide, giving the products indicated: (3) 1 - (4 - methylphenyl) - 1,3,3,6 - tetramethylindane, to give 1-(3-hydroxy-4-methylphenyl)-1,3,3,6 - tetramethyl - 5 - indanol, (2) 1-(3-methylphenyl) - 1,3,3,5 - tetramethyl - indane to give 1-(4-hydroxy-3-methylphenyl)-1,3,3,5-tetramethyl - 6 - indanol, (3) 1 - phenyl-1,3,3-trimethyl-indane to give 1,(4-hydroxyphenyl)-1,3,3 - trimethyl - 5 - indanol, (4) 1 - (4 - methylphenyl) - 1,3 - diethyl - 3,6 - dimethyl - indane, to give 1-(3-hydroxy-4-methyl-phenyl)-1,3-diethyl - 3,6 - dimethyl - 5 - indanol, (5) 1-(3-methylphenyl) - 1,3 - diethyl - 3,5 - dimethylindane, to give 1-(4-hydroxy-3-methylphenyl)-1,3 - diethyl - 3,5 - dimethyl - 6 - indanol, (6) 1 - phenyl - 1,3 - diethyl - 3 - methyl - indane, to give 1 - (4 - hydroxyphenyl) - 1,3 - diethyl-3-methyl-5-indanol.  The products give resins by reaction with halohydrins (see Group IV (a)).ALSO:Resinous products are obtained by reacting an epihalohydrin or a dihalohydrin with a dihydric phenol of the formula: <FORM:0788747/IV (a)/1> R and R1 being hydrogen or alkyl of 1-4 carbon atoms, and R11 and R111 being alkyl of 1-4 carbon atoms.  In examples, resins are obtained when epichlorhydrin is reacted in alkaline solution with (1) 1-(3-hydroxy-4-methylphenyl) - 1.3.3.6 - tetramethyl - 5-indanol; (1) 1 - (4 - hydroxy - 3 - methylphenyl) - 1.3.3.5 - tetramethyl - 6 - indanol; (3) 1 - (4 - hydroxyphenyl) - 1.3.3 - trimethyl-5 - indanol; (4) 1 - (4 - hydroxy - 3 - methylphenyl) - 1.3 - diethyl - 3.5 - dimethyl - 6 - indanol; and (5) 1 - (4 - hydroxyphenyl - 1.3 - diethyl - 3 - methyl - 5 - indanol, and also when (6) glycerol - a a 1 - dichlorhydrin is reacted with 1 - (3 - hydroxy - 4 - methylphenyl) - 1.3-diethyl - 3.6 - dimethyl - 5 - indanol.  The resins obtained may be aftertreated by (1) treatment with polyamines, various diaminoalkanes and polyalkylene polyamines being specified; (2) esterification of the hydroxy groups with fatty acids from caproic upwards; (3) reaction with unsaturated or saturated polycarboxylic acids to give alkyd resins.  The resins may be blended with natural resins, drying oils, cellulose derivatives, alkyd resins, polyester resins, alcohol-modified or non-alcohol-modified aminoplast or phenolic resins, polystyrenes, polyvinyl acetate, polyvinyl chloride, polyacrylonitrile polymercaptans, polyamides and polysulphonamides.