Patent GB-998860-A (GB)
Title: Process for the production of polyesters of phosphorous acid containing free hydroxyl groups
IPC: C08G59/40
Filed: 1962-09-03
Abstract: Polyesters of phosphorous acid containing free OH groups are obtained by transesterifying a trialkyl or a tri(haloalkyl) phosphite in which the alkyl or haloalkyl group contains 1 to 4 carbon atoms with a mixture of a modified or unmodified carbohydrate containing at least four carbon atoms and a monohydric or polyhydric alcohol or with a modified mixture of such a carbohydrate and monohydric or polyhydric alcohol so that at least 3 mols. of hydroxy group are present per mol. of trialkyl or tri(haloalkyl) phosphite.  The carbohydrate or mixture thereof with the alcohol may be modified by treating with an acid or by condensing with an aldehyde, e.g. formaldehyde, in the presence of an acid catalyst, e.g. HBF4 or with a different mono- or polyhydric alcohol; the carbohydrate may also be modified by acylation or alkylation.  The carbohydrate may be a water-soluble monosaccharide, an aligosaccharide, or a polysaccharide including "inter alia" grape sugar, cane sugar, cellobiose, dextrins and starches.  The alcohol may be for example n-octanol, stearyl alcohol, ethylene- or diethylene glycol or polyethylene- or polypropylene glycols, butanediols, hexanediols, butenediol, butinediol, glycerine, trimethylolalkanes, pentaerythritol, hexanetriols, sorbitol or mannitol.  Partial esters or ethers of the specified polyhydric alcohols and halogen-containing alcohols may also be employed. Specified triphosphites are trimethyl, triethyl-, trichloroethyl- and tris-(b -chloropropyl) phosphites. The transesterification is preferably carried out in the absence of water and a catalyst may be present.  Preferred reaction temperatures are from 50 DEG  to 120 DEG C.  The products which should have a phosphorous content of at least 0.5% are generally colourless viscous condensates and are useful as lubricants, as plasticizers for halogen-containing polymers and for the production of epoxy resins.ALSO:Polyesters of phosphorous acid containing free OH groups are obtained by transesterifying a trialkyl or a tri(haloalkyl) phosphite in which the alkyl or haloalkyl group contains 1 to 4 carbon atoms with a mixture of a modified or unmodified carbohydrate containing at least four carbon atoms and a monohydric or polyhydric alcohol or with a modified mixture of such a carbohydrate and monohydric or polyhydric alcohol so that at least 3 mols. of hydroxy group are present per mol. of trialkyl or tri(haloalkyl) phosphite. The carbohydrate or mixture thereof with the alcohol may be modified by treating with an acid or by condensing with an aldehyde, e.g. formaldehyde, in the presence of an acid catalyst, e.g. HBF4 or with a different mono- or polyhydric alcohol; the carbohydrate may also be modified by acylation or alkylation. The carbohydrate may be a water-soluble monosaccharide, an oligosaccharide, or a polysaccharide including "inter alia" grape sugar, cane sugar, cellobiose, dextrins and starches. The alcohol may be, for example, n-octanol, stearyl alcohol, ethylene- or diethylene glycol or polyethylene- or polypropylene glycols, butanediols, hexanediols, butanediol, butinediol, glycerine, trimethylolalkanes, pentaerythritol, hexanetriols, sorbitol or mannitol. Partial esters or ethers of the specified polyhydric alcohols and halogencontaining alcohols may also be employed. Specified triphosphites are trimethyl-, triethyl-, triochloroethyl- and trio-(b -chloropropyl) phosphites. The transesterification is preferably carried out in the absence of water and a catalyst may be present. Preferred reaction temperatures are from 50 DEG  to 120 DEG  C. The products which should have a phosphorus content of at least 0.5% are generally colourless viscous condensates and are useful as lubricants, as plasticizers for halogen-containing polymers and for the production of epoxy resins.