Patent GB-1056542-A (GB)
Title: Organobismuth compounds
IPC: C08G79/00
Filed: 1964-04-24
Abstract: Organobismuth compounds of formulae RaBiX3- a and Ar3BiX2 where a is 1 o 2, R (which may contain an inert substituent) is an alkyl or alkenyl group of <20C, a cycloalkyl group or monocyclic aryl group, Ar is an unsubstituted or inertly substituted monocyclic aryl group; and X is a group of formula -OOC(R1)OH, -OOC(R1)NH2 or -S(R1)OH, R1 being an unsubstituted or substituted divalent saturated or ethylenically unsaturated aliphatic group containing <20C, a phenylene or divalent araliphatic group are prepared by  (a) RaBiZ3- a + (3-a)MX -> RaBiX3- a + (3-a)MZ, or  (b) R3Bi + (3-a)HX -> RaBiX3- a + (3-a)RH  where R, R1, a and X are as defined above, M is hydrogen or a metal, and Z is a replaceable group such as -OH,-U or -O-, or (c) Ar3BiZ12 + 2MX -> Ar3BiX2 + 2MZ1  where Ar, R1, M and X are as defined above and Z1 is a replaceable group such as O or CO3.  In preparations the following compounds were prepared (1) phenylbismuth bis (p-hydroxybenzoate) from triphenylbismuth and p-hydroxybenzoic acid, (2) triphenylbismuth bis (p-aminobenzoate) from triphenylbismuth carbonate and p-aminobenzoic acid, (3) dioctylbismuth ricinoleate from dioctylbismuth chloride and ammonium ricinoleate and (4) phenylbismuth bis (2-hydroxyethylmercaptide) from triphenylbismuth with 2-mercaptoethanol.ALSO:A polymer containing organobismuth groups is prepared by reacting an organic polyisocyanate with an organobismuth compound of formula RaBiX3- a or Ar3BiX2 where a is 1 or 2, R (which may be substituted by an inert group) is an alkyl or alkenyl group of <20 C, a cycloalkyl group or monocyclic aryl group; Ar is an unsubstituted or inertly substituted monocyclic aryl group; and X is a group of the formula -OOC(R1)OH, -OOC(R1)NH2 or -S(R1)OH, R1 being an unsubstituted or substituted divalent saturated or ethylenically unsaturated aliphatic group of <20 C, a phenylene or divalent or aliphatic group.  The reaction mixture may also include a polyether a polyester, e.g. polypropylene oxide or the hydroxyl terminated polyester of adipic acid, ethylene glycol and propylene glycol.  Foamed polyurethanes or polyureas may be obtained by incorporating the organobismuth compounds in foam forming recipe.  In examples tolylene diisocyanate was reacted with (1) phenylbismuth bis-(2-hydroxyethyl-mercaptide), (2) phenylbismuth bis-hydroxyacetate, (3) hydroxyl terminated polyether and phenylbismuth bis-(2-hydroxyethylmercaptide) in the presence of stannous octoate, (4) hydroxyl terminated polyether, water and phenylbismuth bis-(2-hydroxyethylmercaptide) in the presence of silicone, N-ethylmorpholine, stannous octoate and triethylene diamine to form a polyurethane foam, (5) phenylbismuth bis-(f-aminobenzoate) with the other reactants as in (4) to give a polyurethane containing urea linkages, (6) phenyl bis-(f-hydroxybenzoate) in toluene.ALSO:A bacteriostatic composition comprises a carrier and as an active ingredient a polymer containing organobismuth groups prepared by reacting an organic polyisocyanate with an organobismuth compound of formula Ra Bi X3-a or Ar3 Bi X2 wherein a is 1 or 2, R (which may contain an inert substituent) is an alkyl or alkenyl group containing <20C, a cycloalkyl or a monocyclic aryl group; Ar is an unsubstituted or inertly substituted monocyclic aryl group; and X a group of formula -OOC(R1) OH, -OOC(R1)NH2, or -S(R1)OH, R1 being an unsubstituted or substituted divalent saturated or ethylenically unsaturated aliphatic group containing <20C, a phenylene group or divalent araliphatic group. The composition may also contain other known active compounds, e.g. pentachlorophenol, a triorganotin compound, copper 8 quinolinolate, a bisphenol, O phenyl phenol, a polybrominated salicylanilide or a metal (e.g. Zn) dialkyldithiocarbamate.