Patent GB-889652-A (GB)
Title: Liquid washing agent incorporating glycol derivatives containing peroxide groups
IPC: C11D3/39
Filed: 1958-02-27
Abstract: A liquid washing agent incorporates the product obtainable by addition of an alkylene oxide and a hydroperoxide of the formula R-O-O-H, wherein R is an organic residue which is linked to the peroxide residue by a non-aromatic carbon atom (for preparation see Group IV(b)).  Preferred hydroperoxides contain 1-30 carbon atoms and preferred alkylene oxides contain 2-10 carbon atoms. The term alkylene oxide includes styrene oxide.  Peroxide stabilizers, e.g. silicates of calcium, magnesium, aluminium, and tin, and hydrated oxides or hydroxides of tin, and heavy metal chelating compounds such as ethylenediamine tetracetic acid, nitrilo-triacetic acid and their salts may be incorporated in the peroxides during their preparation. In an example, a washing agent consisting of alkylbenzene sulphonate, oleyl sulphate, coconut fatty acid ethanolamide, coconut alcohol, Na2-CO3, Na4P2O7, Na5P3O10, MgSiO3, Na2-O3,3SiO2, Na2SO4, an optical brightener and water is dissolved in water so that the solution contains 6 gms. per litre of the washing agent and to this is added an addition product of ethylene oxide and tert.-butylhydroperoxide and the solution is used for washing with boiling of linen or cotton. The bleaching action may be intensified by addition of benzoic anhydride.ALSO:Glycol ethers or polyethers containing peroxide groups are prepared by adding alkylene oxides to organic hydroperoxides in the presence of boron fluoride etherates which are derived from ethers containing 2 to 8 carbon atoms.  The hydroperoxides used have the general formula R-OOH where R signifies an organic residue which is linked to the peroxide residue by a non-aromatic p  carbon atom, and may contain 1-30, preferably 1 to 20, carbon atoms and be derived from saturated or unsaturated, straight or branched chain compounds or aromatic or nonaromatic cyclic compounds.  The hydroperoxides with cyclic organic residues may have 4- to 8-membered rings which may be fused together and which may contain hetero atoms, such as oxygen or sulphur.  The hydroperoxides may contain hydrocarbon residues only or may be substituted by different hetero-atoms or hetero-atoms groups, such as ether groups, thioether groups, carboxylic ester groups and halogen atoms, and may contain several peroxide groups.  A list of suitable hydroperoxides is given.  Preferred alkylene oxides are those containing 2-10 carbon atoms and including styrene oxide, ethylene oxide being the most preferred.  The alkylene oxides are generally used in amounts of at least one mol and not exceeding 25 mol per mol of hydroperoxide.  Temperatures up to 100 DEG C., preferably in the range 40 DEG C.-80 DEG C., are suitable.  The catalysts are used in amounts of 0.1% to 10% by weight, preferably 0.5% to 1% by weight, referred to the hydroperoxide, the compound of boron fluoride with diethyl ether being the preferred catalyst. Known stabilizers for peroxides can be added to the reaction mixture, such as silicates of calcium, magnesium or aluminium or the hydrated oxides, hydroxides or silicates of tin, nitrilotriacetic acid or ethylenediamine tetraacetic acid or their salts.  The products which contain 1-4 glycol residues may be used as emulsifiers and are particularly suitable as peroxidic catalysts for emulsion polymerisations.  In Examples (1) t-butyl hydroperoxide reacts with 1.95 mol of ethylene oxide per mol of hydroperoxide; (2) a mixture of t-butylhydroperoxide and di-t-butyl-peroxide reacts with 1.6 mol of ethylene oxide per mol, giving glycol ethers containing 1 to 5 glycol ether residues per molecule; (3) the same mixture reacts with 4.95 mol ethylene oxide per mol; (4) t-amylhydroperoxide reacts with 3.95 mol ethylene oxide per mol; (5) n-octylhydroperoxide reacts with 5.65 mol of ethylene oxide per mol; (6) tbutylhydroperoxide reacts with 7.7 mol ethylene oxide per mol; (7) sec-butyl-hydroperoxide reacts with 5.65 mol ethylene oxide per mol; (8) sec-butyl-hydroperoxide reacts with 13 mol ethylene oxide per mol; (9) n-octylhydroperoxide reacts with 12.2 mol ethylene oxide per mol; (10) and (11) t-butyl-hydroperoxide reacts with styrene oxide; (12) t-butylhydroperoxide reacts with propylene oxide; (13) t-butyl-b -ethoxy-peroxide obtained by distillation of the product of (2) is reacted with a further 11 mols of ethylene oxide.  The products may be used in liquid washing agents.ALSO:A liquid washing agent incorporates the product obtainable by addition of an alkylene oxide and a hydroperoxide of the formula R-O-O-H, wherein R is an organic residue which is linked to the peroxide residue by a non-aromatic carbon atom (for preparation see Group IV (b)).  Preferred hydroperoxides contain 1-30 carbon atoms and preferred alkylene oxides contain 2-10 carbon atoms. The term alkylene oxide includes styrene oxide.  In an example, a washing agent consisting of alkyl-benzene sulphonate, oleyl sulphate, coconut fatty acid ethanolamide, coconut alcohol, Na2CO3, Na4P2O7, Na5P3O10, MgSiO3, Na2O.3.3SiO2, Na2SO4, an optical brightene and water is dissolved in water so that the solution contains 6 gms per litre of the washing agent and to this is added an addition product of ethylene oxide and tert-butylhydroperoxide and the solution is used for washing, with boiling, of linen or cotton.  The bleaching action may be intensified by addition of benzoic anhydride.