Patent GB-1095228-A (GB)
Title: Alkyl esters of glutamic acid aspartic acid, method for their preparation, and derivatives thereof
IPC: A23D9/007
Filed: 1964-12-29
Abstract: Increased viscosity or flexibility is imparted to liquid and solid hydrocarbons such as petroleum oil and fractions thereof, petroleum oil jellies, paraffin waxes, montan wax, benzene, toluene, xylene, naphthalene, benzyl naphthalene dimethyl naphthalene, ethyl naphthalene, anthracene, gasoline and kerosine, to give thickened or solid heating fuels or "Napalin" bombs; to hydrogenated or unhydrogenated oils and fats of animal or vegetable origin such as tallow, lard and soyabean, olive, rapeseed, safflower, peanut, corn, fish, seal and whale oils, to give solid shortening agents or margarine-like products; to natural waxes such as carnauba wax, beeswax and spermaceti; or to mixtures of any of the above classes by addition thereto of polymers containing units of the formula <FORM:1095228/C4-C5/1> formed by polymerizing novel N-carboxy anhydrides of the formula <FORM:1095228/C4-C5/2> wherein R represents an alkyl group containing 7 or more carbon atoms and n is 0 or 1, alone or with other N-carboxy anhydrides containing a group of the structure <FORM:1095228/C4-C5/3> Examples describe the thickening of corn oil and the further addition of sorbitan trioleate, polyoxyethylene sorbitan trioleate and water to form a margarine; the thickening of a hydrocarbon solvent and of a wax/oil blend; thickening of motor oils to form ashless greases; and the addition to paraffin wax to give a more flexible product.ALSO:Novel N-carboxy anhydrides of the formula <FORM:1095228/C3/1> wherein R represents an alkyl group containing 7 or more carbon atoms and n is 0 or 1, are homopolymerized or copolymerized with other N-carboxy anhydrides containing a group of the structure <FORM:1095228/C3/2> to give products containing units of the formula <FORM:1095228/C3/3>  The polymerization is effected in an inert solvent such as methylene chloride and in the presence of a basic catalyst such as tributylamine, variations in choice of solvent and basic catalyst giving different degrees of polymerization.  Examples describe the preparation of poly-omega-n-dodecyl-L-glutamate, poly - omega - n - tetradecyl- - L - glutamate, poly - omega - n - hexadecyl - L - glutamate, poly - omega - n - octadecyl - L - glutamate, poly - omega - n - eicosyl - L glutamate, poly-omega - n - octyl - L - glutamate, poly - omega - n - octadecyl - L - aspartate, poly-omega - n - decyl - L - glutamate, copolymers of omega - n - octadecyl - L - glutamate - N - carboxy anhydride and omega - methyl - L - glutamate - N -carboxy anhydride, and a copolymer of omega-n-octadecyl - L - glutamate - N - carboxy anhydride and omega - n - tetradecyl - L - glutamate - N - carboxy anhydride.  The above polymers may be used to thicken oils or may be dissolved in benzene and mixed with powdered polypropylene, the benzene removed and the resulting modified polypropylene moulded to give a product having improved flexibility (see Examples T10 and T11). Similar additions may be made to polyethylene and polystyrene.ALSO:Novel compounds of the formula R-CH2-OOC-CH2-(CH2)n-CH(NH2)COO wherein R represents an alkyl group containing 7 or more carbon atoms and n is 0 or 1, and acid and base addition salts of such compounds, are prepared by reacting an acid addition salt of aspartic or glutamic acid with an alkanol of the formula RCH2OH in the presence of a strong acid and a tertiary primary alcohol which is a co-solvent for the said reactants followed, if desired, by reaction with an appropriate amount of a base to provide a product in the free acid or base addition salt form.  The above novel compounds may be reacted with phosgene to give N-carboxy anhydrides of the formula <FORM:1095228/C2/1> which may be subsequently homopolymerized or copolymerized with other N-carboxy anhydrides containing a group of the structure <FORM:1095228/C2/2> to give polyamide products which are used for thickening esters such as isopropyl myristate.