Patent GB-909367-A (GB)
Title: Production of polysulfonates
Inventor: DEMMLER KURT
IPC: C08G65/34
Filed: 1961-01-26
Abstract: It is stated that the reaction products of compounds containing 2 or more active hydrogen atoms with vinyl sulphonic esters of polyhydroxy compounds may be used in varnishes or lacquers.  In examples 12, 14, 18, 19, and 23-26, metal sheets are coated with solutions of such reaction products, in example 12, with the addition of an epoxy resin, dried at room temperature for 18 hours, 3 days, 1 day, 16 hours, 3 days, 1 day, 1 day and 3 days respectively and cured for 1 hour at 70 DEG C. in Example 12 and at 100 DEG C. in other cases.ALSO:The esters are prepared by reacting at between -50 DEG and +200 DEG C., a vinyl sulphonic acid ester of an organic polyol with an organic compound which contains at least two hydrogen atoms in the molecule, other than as water or alcohol of crystallization or as acidic groups, capable of reacting with the vinyl esters to form polysulphonates, e.g. alkenols, phenols, amines, alkanolamines, amides, imines, bislactams, ureas, thioureas, guanidines, hydrazides, sulphonamides or mercaptans; many compounds are listed.  The vinyl sulphonic acid esters may be prepared from aromatic, aliphatic acyclic, or heterocyclic polyols, from hydroxyaryl alkanes, bis(hydroxyaryl) sulphones, bis-(hydroxybenzyl) benzenes, novolacs, and phenol-acrolein condensates.  Many specific compounds are listed. In some cases, particularly when polyols or polythiols are used, 0,1 to 10% mol. based on the polyol or polythiol, of a basic-reacting substance may be added as catalyst, e.g. oxides, hydroxides, carbonates, borates and phosphates of alkali and alkaline earth metals; tertiary amines; quaternary ammonium salts which dissociate in hot water; alcoholates and phenolates.  When phenols or alkanols are the reactants, the preferred catalyst is the phenolate or alcoholate derived therefrom, which may be prepared in situ, e.g. by addition of KOH or NaOH.  Alcoholates of monohydric alcohols also act as chain-stoppers when bifunctional reactants are used, particularly when the active hydrogen atoms are attached to nitrogen atoms.  The process may be carried out in solution, in aqueous emulsion, or in suspension, or without the presence of diluents.  Suitable solvents are: H2O, butanol, benzene, toluene, methylene chloride, ethylene chloride, chloroform, carbon tetrachloride, or mixtures thereof. Alcohols are not suitable when polyols are being used as reactants. The reaction may be carried out in the presence of compounds which tend to form resins under the same conditions, e.g. epoxides (Example 4) and isocyanates.  Polysulphonic esters prepared from nitrogenous compounds and containing excess NH groups may be used to cure epoxy resins (Examples 12, 13).  Resins having excess vinyl groups may be cured by resins having excess active hydrogen and vice versa.ALSO:It is stated that the reaction products of vinyl sulphonic esters of polyhydroxy compounds with compounds containing 2 or more active hydrogen atoms may be used to make "expanded porous articles." Example 21 discloses the reaction of 20 parts finely divided carbonate prepared from bis-(4-amino-cyclohexyl)-methane, and 48 parts of resorcinol di-(vinyl sulphonic ester) on heating at 130 DEG C. for 1 hour to give a large-pored, brittle foam.