Patent GB-973905-A (GB)
Title: Improvements in and relating to lactone polymers
Inventor: COX EUGENE FLOYD
IPC: C08G63/82
Filed: 1962-02-13
Abstract: Metal amide-alcoholates and -phenolates of formula H2N-M-OR1 where M is Mg, Ca, Zn, Sr, Cd or Ba and R1 is a hydrocarbon radical, e.g. alkyl, cycloalkyl, aryl, alkaryl, aralkyl, alkenyl or cycloalkenyl may be prepared (a) by reacting an alkaline earth metal hexammoniate with an epoxide, preferably in the presence of liquid ammonia or an inert organic vehicle (e.g. a hydrocarbon or an ether); or (b) by reacting an amide of any of the metals or an alkaline earth metal hexammoniae with an organic monohydric compound, preferably in a liquid ammonia medium or an inert organic vehicle (e.g. a hydrocarbon); or (c) by reacting an alkaline earth metal hexammoniate with a saturated aliphatic aldehyde, preferably in a liquid ammonia medium.  A catalyst of indefinite composition is made by reacting 1 mol. of an alkaline earth metal hexammoniate with 0.3-1.0 mols of an olefin oxide and 0.2-0.9 mols of an organic nitrile in a liquid ammonia medium and subsequently evaporating the excess ammonia from the catalyst.  The catalyst contains groups of formula R-O-M-wherein R is derived from the olefin oxide (e.g. is ethyl when ethylene oxide is used) and M is the alkaline earth metal. It also contains alkylindeneimine formed by the reduction of the organic nitrile by the metal in liquid ammonia.ALSO:Polyesters are made by polymerizing certain lactones having 6-18 atoms in the ring in the presence of (1) an amide and/or an amidealcoholate of magnesium, calcium, zinc, strontium, cadmium or barium or (2) a catalyst which is prepared by reacting 1 mol of an alkaline earth metal hexammoniate with from 0.3 to 1.0 mol of an olefin oxide and from 0.2 to 0.9 mol of an organic nitrile in a liquid ammonia medium and subsequently evaporating the excess liquid ammonia from the catalyst.  The lactones have the formula <FORM:0973905/C3/1> where R is hydrogen, alkyl, aryl, alkaryl, aralkyl, cycloalky, halo, haloalkyl, alkoxyalkyl, alkoxy or aryloxy; A is -O-, -S- or a divalent saturated aliphatic hydrocarbon group; x is 1-15; y is 1-15 and z is 0 or 1; with the proviso that (a) x+y+z cannot equal 2 or 3; (b) the total number of atoms forming the cyclic ester ring does not exceed 18; (c) the total number of organic substituents attached to the carbon atoms contained in the cyclic ester ring does not exceed 4; (d) from 2-4 continuously linked carbon atoms contained in the cyclic ester ring can represent a portion of a saturated cycloaliphatic hydrocarbon nucleus containing 4-10 carbon atoms; and (e) the four R variables attached to any two adjacent carbon atoms contained in the cyclic ester ring can represent a portion of an aromatic hydrocarbon nucleus which is fused to the ring of the cyclic ester. Polymerization is carried out at 0 DEG -250 DEG C. either by a batch or continuous process and may be effected in the presence or the absence of an inert organic liquid or a mixture of mutually immiscible inert organic liquids.  The polyesters have a molecular weight of 900-100,000 and are useful in the manufacture of cosmetics, polishes, waxes, thickening agents for lubricants, sizes, anti-static agents, coating compositions, impregnants, adhesives, oil additives, binders for linoleum, shaped articles, fibres, films and plasticizers for vinyl resins.  Examples disclose the polymerization of (11)-(14) epsilon-caprolactone; (15) isomeric methyl epsilon-caprolactones; (16) isomeric octyl epsilon-caprolactones; (17) delta-valerolactone; (18) beta-methyl-delta-valerolactone; (19)-(21) a mixture of epsilon-caprolactone and beta-methyl-delta-valerolactone; (22) zeta-enantholactone; (23)-(24) a mixture of zeta-enantholactone and epsilon-caprolactone; (25) 2-keto-1, 4-dioxane; (26)-(27) a mixture of epsilon-caprolactone and delta-valerolactone; (28) a mixture of epsilon-caprolactone and mixed dimethyl epsilon-caprolactones; (29) a mixture of epsilon-caprolactone and mixed octyl epsilon-caprolactones; (30) ortho-(2-hydroxyethyl)-phenyl acetic acid lactone; (32) epsilon-caprolactone; (33) a mixture of delta-valerolactone and beta-methyl-delta-valerolactone; (34) a mixture of epsilon-caprolactone and mixed methyl epsilon-caprolactones; (35) mixed octyl epsilon-caprolactones; (36) a mixture of 2, 4-dimethyl-4-methoxymethyl-5 hydroxypentanoic acid lactone and epsilon-caprolactone; (37) ortho-(2-hydroxyethyl)-phenylacetic acid lactone; (38) epsilon-caprolactone; (39) delta-valerolactone; (40) zeta-enantholactone; (41)-(43) a mixture of epsilon-caprolactone and beta-methyl-delta-valerolactone; (44)-(45) a mixture of zeta-enantholactone and epsilon-caprolactone; (46) epsilon-caprolactone; (47) 2-keto-1, 4-dioxane.