Patent GB-1483859-A (GB)
Title: Polyalkylene oxide-containing urethane polyols containing sulphonic acid groups
IPC: C07C301/00
Filed: 1975-03-11
Abstract: 1483859 Polyalkylene oxide-containing urethane polyols; antistatic agents BAYER AG 11 March 1975 [14 March 1974] 10045/75 Headings C3R and C3P [Also in Division C2] Polyalkylene oxide-containing urethane polyols have the general formula wherein X represents an NH 4  radical or an alkali metal atom, R 1  represents a linear or branched C 2 -C 7  aliphatic group, or an aromatic group which consists of one ring or 2 fused rings, the aromatic group being optionally substituted by at least one halogen, by at least one C 1 -C 5  aliphatic group, by at least one nitro group or by at least one further sulphonic acid group, R 2  represents hydrogen or a methyl group, R 3  and R 4  each represent a divalent linear or branched C 2 -C 10  aliphatic group, n is 1-50 and y is 1 or 2. The urethane polyols may be prepared either by reacting an unsaturated C 2 -C 7  aliphatic alcohol with ethylene oxide and/or propylene oxide, phosgene and a secondary amine containing 2 free OH groups which are each linked to the N atom through a divalent linear or branched C 2 -C 10  aliphatic group and subsequently adding an alkali metal or ammonium bisulphite to the reaction mixture such that the bisulphite adds to the carbon-carbon double bond of the alcohol group; or by reacting either a linear or branched C 2 -C 7  aliphatic hydroxysulphonic acid or an appropriate aromatic hydroxysulphonic acid each in the form of its alkali metal or ammonium salt with ethylene oxide and/or propylene oxide, phosgene and a secondary amine containing 2 free OH groups as defined above. The preferred secondary amines are diethanol-amine and diisopropanolamine. The preferred unsaturated aliphatic alcohol is allyl alcohol but may be but - 2 - ene - 1,4 - diol, hex - 3 - ene - 2,5 - diol or 2 - methylpropane - 1,3 - diol, and the preferred aliphatic and aromatic hydroxysulphonic acids are 2-hydroxy-ethane-sulphonic acid and p-phenolsulphonic acid. The resulting urethane diols may be reacted with long-chain aliphatic isocyanates to form compounds which can be used as additives in an amount of 5% wt. in a polyacrylonitrile spinning solution in dimethylformamide for imparting antistatic properties to the filaments obtained therefrom. In Examples 5-12 urethane polyols are prepared by first ethoxylating allyl alcohol in the presence of sodium methanolate as catalyst, then phosgenating the resulting product using toluene as solvent and reacting the resulting chlorocarbonic acid ester with diethanolamine in the presence of aqueous NaOH. The product is then reacted with aqueous sodium bisulphite. Example 13 is similar except that propylene oxide is used as alkoxylating agent. In Examples 14 and 15 urethane diols are prepared by first ethoxylating sodium - p - phenolsulphonate or sodium 2,6 - dichloro - p - phenolsulphonate in the presence of aqueous NaOH, followed by phosgenation and reaction with diethanolamine as above. In a further example stearyl isocyanate is reacted with a urethane diol of the formula and the resulting triurethane is added as an antistatic agent to polyacrylonitrile.