Patent GB-932811-A (GB)
Title: Bis and polyphenols and production thereof
Inventor: SIMMONS PAUL
IPC: C08G59/24
Filed: 1960-06-02
Abstract: Epoxide resins and polycarbonates are prepared from bis and polyphenols of the general formula <FORM:0932811/IV(a)/1> wherein symbols X, Y and Z are the same or different and are hydrogen atoms, or alkyl groups and the benzene rings identified as A and B may carry additional substituents selected from alkyl, nitro, hydroxy and halogen and/or may be fused to other aromatic or to cycloaliphatic rings.  The epoxide resin is prepared by dissolving the phenol in epichlorohydrin and adding thereto sodium hydroxide, removing excess epichlorohydrin by distillation, dissolving the residue in trichloroethylene and evaporating to give a viscous brown resin.  A hardenable composition is made by heating this resin to a temperature of 120 DEG C., and dissolving in phthalic anhydride.  Castings were made by pouring the composition whilst still at 120 DEG C. into moulds of the required dimensions and subsequently curing for 6 hours at 120 DEG C., followed by 16 hours at 180 DEG C.  Another hardenable composition is made by heating the resin and dissolving in 4,41-diaminophenyl-methane.  A polycarbonate is prepared by melting together the phenol, diphenylcarbonate and lithiumhydride in an atmosphere of nitrogen.  Specifications 641,250 and 782,072 are referred to.ALSO:The invention comprises bisphenols and polyphenols of the general formula <FORM:0932811/IV(a)/1> wherein the symbols X, Y, Z are the same or different and are hydrogen atoms or alkyl, groups and the benzene rings identified as A and B may carry additional substituents selected from alkyl, nitro, hydroxy and halogen and/or may be fused to other aromatic or to cycloaliphatic rings.  The compounds are prepared by reacting a compound of the formula <FORM:0932811/IV(a)/2> with phenols of the general formula <FORM:0932811/IV(a)/3> the symbols having the meanings as indicated above, and the benzene ring B being unsubstituted in a position ortho or para to the phenolic hydroxy group, the reaction being effected in the presence of an acid or acid-reacting catalyst under substantially anhydrous conditions.  Suitable a,a1-dihydroxydialkyl benzene compounds of general formula II are 1,4-bis-(a-hydroxyethyl-) benzene, 1,4-bis-(a-hydroxypropyl-) benzene, 1,4-bis-(a-hydroxy-isopropyl-) benzene, 1,4-bis-(a-hydroxy-isobutyl-) benzene, 1,3-bis-(a-hydroxyethyl-) benzene, 1,3-bis-(a-hydroxypropyl-) benzene, 1,3-bis-(a-hydroxyisopropyl-) benzene, and 1,3(a-hydroxyisobutyl-) benzene.  Suitable phenols of the general formula III are o-, m-, and p-cresol, xylenols, o-, m-, and p-ethyl phenol, n-propyl phenol, n-butyl-phenol, tert-butyl-phenol, pseudocumenol, durenol, carvacrol, thymol, o-allyl phenol, o-cyclohexyl-phenol, o-, m-, and p-chloro-phenol, o-, m-, and p-nitrophenol, hydroquinone, resorcinol, pyrocatechol, 1-naphthol, 2-naphthol, 1,4-naphtho-hydroquinone, bis-(4-hydroxyphenyl-) methane, 2,2-bis-(41-hydroxyphenol-)propane and in particular phenol itself. Suitable acid catalysts are strong inorganic or organic acids such as hydrogen chloride gas, concentrated hydrochloric acid, sulphuric acid, phosphoric acid, toluene-p-sulphonic acid, ion exchange resins such as sulphonated polystyrene and Lewis acids such as boron trifluoride and stannic chloride.  Examples are given of the preparation of a,a1-Bis(phydroxyphenyl)- p-diisopropyl benzene, a,a1-Bis(p-hydroxy-m-methyl-phenyl)-p-diisopropyl benzene, a,a1-Bis(p-hydroxyphenyl)-m-diisopropyl benzene, a,a1-Bis(p-hydroxy-m-methyl-phenyl)-m-diisopropyl benzene by reacting respectively a,a1-dihydroxy-p-diisopropyl benzene with phenol and o-cresol, and a,a1-dihydroxy-m-diisopropyl benzene with phenol and o-cresol.  Specifications 641,250, 782,072 and U.S.A. Specification 2,828,043 are referred to.