Patent GB-877134-A (GB)
Title: Improvements in or relating to polyethers
IPC: C08G59/20
Filed: 1957-08-29
Abstract: Polyethers are derived by opening the epoxy ring or rings in an alcohol, acid, ester, amide, nitrile or acid halide having at least one C10-C22 chain with the grouping <FORM:0877134/IV (a)/1> wherein m is a whole number from 0-15, p a whole number from 1-15, x is 1, 2 or 3 and m+ 3x+p+1=10-22.  Rupture of the rings is effected with a Lewis acid catalyst, examples of which are boron trifluoride, zinc chloride, aluminium chloride, stannic chloride, silicon tetrachloride, and perchloric acid.  The catalyst may be used as a complex with water, an alcohol or an ether and the catalyst or complex may be used in the presence of (e.g. as a solution in) water, an alcohol or an ether.  The epoxy starting materials are preferably based on naturally occurring unsaturated fatty acids.  Polymerized acids or esters may be treated to form salts, e.g. sodium, potassium or ammonium salts.  In all the examples BF3-etherate was employed as catalyst.  (1), 9, 10-epoxystearic acid was polymerized.  The product may be purified by saponification followed by urea adduct refining; (2) methyl-9, 10-epoxy stearate was polymerized, and purified by urea adduct formation, liquid-liquid extraction, propane refining or vacuum distillation.  Hydrolysed it yields a pure form of the acid obtained in Example (1); (3) Partially epoxidized menhaden or soya bean oil (1,36% oxirane oxygen) was polymerized.  The products were air-drying oils; (5) 9, 10-epoxy oleyl acetate was polymerized in presence of methyl "Cellosolve" (Registered Trade Mark).  Hydrolysed with alcoholic NaOH, it yielded the polyether alcohol; (6) 9, 10-epoxystearamide was polymerized; (7) 9, 10-epoxy stearyl nitrile was polymerized; (8) 9, 10-epoxystearyl chloride was polymerized. (4) Other epoxides which were polymerized were butyl epoxystearate, hexyl epoxystearate, tetrahydrofurfuryl epoxystearate, methyl esters of epoxidized soya bean oil fatty acids, epoxidized distilled acetylated monoglyceride of soybean oil or lard oil, methyl Cellosolve, 2-ethyl hexyl, butyl or iso-propyl esters of epoxidized soybean oil fatty acids.  These "linear" polymers are suitable as lubricant additives.  Their salts are water-soluble and surface-active.  Using poly-epoxide starting materials, cross-linked polymers may be obtained.  They are useful for casting or moulding or as additives to natural or synthetic rubber.  In Example (9) epoxidized soybean oil (6,2% epoxy oxygen) was polymerized in presence of methyl Cellosolve; (10) epoxidized lard oil (3,98% epoxy oxygen) was similarly polymerized; (11) epoxidized linseed oil (8,2% epoxy oxygen) was polymerized in presence of tetraethylene glycol; (12) dipentaerythritol hexa (epoxy) stearate was polymerized in presence of methyl Cellosolve; (13) The product of Example (9) was saponified with alcoholic KOH and acidified to yield the polyether polymer of epoxy stearic acid.  Soluble poly soaps of other polymerized epoxidized oils may be similarly prepared.  Soluble products may be prepared from polyepoxides by moderating catalyst activity with water or alcohol.  Glycol esters of epoxy fatty acids are specifically mentioned as suitable starting materials. Specifications 737,697 and 877,135 also are referred to.  Reference has been directed by the Comptroller to Specification 783,740.