Patent GB-859645-A (GB)
Title: Process for preparing lactone adducts and polyesters
IPC: C08G63/08
Filed: 1957-04-15
Abstract: A polyester or lactone adduct (see Group IV(b)) is made by heating to between 50 DEG C. and 250 DEG C. a lactone having at least six carbon atoms in the ring with an organic compound containing at least one alcoholic hydroxyl group or a primary or secondary amino group attached directly to carbon in the presence of a catalyst which is an organic carboxylic acid or anhydride (e.g. acetic acid or anhydride, 2-ethyl hexanoic acid or benzoic acid).  Preferred lactones and initiators are as specified in Specification 859,643.  The polyesters may be used as plasticizers for copolymers of 97% vinyl chloride and 3% vinyl acetate.  In examples products were made by reacting epsilon-caprolactone with (1) (4) and (7) 2-ethyl -1, 3- hexanediol; (2) trimethylol propane; (3) glycerol; (5) ethylene glycol; (6) propylene glycol (9) diethylene triamine; (10), (11) and (12) 2-ethylhexanol; (13) n-hexanol; (14) a 10 carbon OXOalcohol; (15) cyclohexanol; (16) the butyl ether of ethylene glycol; (17) allyl alcohol; (18) heptanol-3; (19) 4-methyl-pentanol-2, (20) OXOdecanol. In Example (8), a polyester was made by reacting a mixture of epsilon-caprolactone and trimethyl-epsiloncaprolactone with 2, 2-diethyl-1, 3-propanedrol.  Specification 859,642 also is referred to.ALSO:A lactone adduct or a polyester (see Group IV (a)) is made by heating at 50 DEG -250 DEG C. a lactone having at least six carbon atoms in the ring with an organic compound containing at least one alcoholic hydroxyl group or a primary or secondary amino group attached directly to carbon in the presence of a catalyst which is an organic carboxylic acid or anhydride (e.g. acetic acid or anhydride, 2 ethylhexanoic acid, or benzoic acid).  Preferred lactoned, hydroxyl compounds and amino compounds are as specified in Specification 859,643.  The reaction can be represented by the equation: <FORM:0859645/IV(b)/1> where n is at least four, at least n + 2 R's are hydrogen and the remaining R's are substituents selected from the group consisting of hydrogen, alkyl, cycloalkyl, alkoxy and single ring aromatic hydrocarbon radicals; R1 is an aliphatic, cyclo aliphatic, aromatic or heterocyclic radical, y is an integer and Y is -O-, NH- or NR11-, where R11 is an alkyl, aryl, aralkyl or cycloalkyl radical; the average value of x is a/y and at least one; and the L's stand for groups having the formula:  <FORM:0859645/IV(b)/2> Thus the initial reaction product of epsilon caprolactone with an amino alcohol of formula HOR1NH2 is a compound of formula: <FORM:0859645/IV(b)/3> That of episilon caprolactone with a monoamine of formula R1NH2 is a compound of formula <FORM:0859645/IV(b)/4> In examples, products were made by reacting epsilon-caprolactone with (1), (4) and (7) 2-ethyl-1, 3-hexanediol; (2) trimethylol propane; (3) glycerol; (5) ethylene glycol; (6) propylene glycol; (9) diethylene triamine; (10), (11) and (12) 2-ethylhexanol; (13) n-hexanol; (14) a 10 carbon OXO-alcohol; (15) cyclohexanol; (16) the butyl ether of ethylene glycol; (17) allyl alcohol; (18) heptanol-3; (19) 4-methyl-pentanol -2; (20) OXO-decanol.  In Example (8), a polyester was made by reacting a mixture of epsilon-caprolactone and trimethyl-epsilon-capro lactone with 2, 2-diethyl-1, 3-propanediol. Specification 859,642 also is referred to.