Patent GB-854673-A (GB)
Title: Complex ester compositions and process for their manufacture
Inventor: CRITCHLEY STUART WALTER
IPC: C08G63/16
Filed: 1958-05-23
Abstract: Complex polyesters of dicarboxylic acids, glycols and monohydric alcohols, of general formula: <FORM:0854673/IV(a)/1> R1 where n represents an average value of 1 or above, R represents saturated aliphatic hydrocarbon groups, R1 saturated aliphatic groups with a chain of 4 to 20 carbon atoms at least one being branched, R6 methyl or ethyl groups, and R7 saturated aliphatic hydrocarbon groups of 1 to 4 carbon atoms are the predominant proportion in compositions with a viscosity at 25 DEG C. of from 400 to 50,000 centipoises which may be used as plasticizers for thermoplasts such as polyvinyl chloride. The esters are prepared by heating in the absence of an esterification catalyst and air, a saturated dicarboxylic acid HOOC R1 COOH and a mixture of acids at least one of which is a branched chain acid, e.g. 2-ethyl-sebacic acid, 2 : 5 diethyl, 2 : 2 : 4 trimethyl, and 2 : 4 : 4 trimethyl adipic acids, or a mixture of 72-80% 2-ethyl sebacic acid, 12-18% 2 : 5 diethyl adipic acid and 6-10% sebacic acid, known as iso-sebacic acid, a 2 : 2 dialkylene propylene glycol e.g. neopentyl glycol or 2-methyl-2-n-propyl-1-3 propane diol, and at least one monohydric alcohol e.g. 2-ethyl hexanol and 3 : 5 : 5 trimethyl hexanol.  In examples, isosebacic acid, 2-ethyl hexanol and neopentyl glycol; and iso-sebacic acid, 2-ethyl hexanol and 2-methyl-2-n-propyl-1 : 3-propane diol are heated together under nitrogen in two stages, of 1 hour up to 130 DEG C. and 7 hours from 130 to 200 DEG C., a further amount of diol added and the heating continued further at 200 DEG C. and then under vacuo at 200 DEG C. to an acid value below 5 mgm. KOH/gm.  Compositions of polyvinyl chloride, a paste of white lead and dioctyl phthalate, and the esters are described.  The compositions may also be used as synthetic lubricants, or thickeners for saturated diester lubricants.ALSO:Complex polyesters of dicarboxylic acids, glycols and monohydric alcohols, of general formula: ROO CR1 COO [CH2. C(R6)(R7). CH2OOC. R1COO]n R where n represents an average value of 1 or above, R represents saturated aliphatic hydrocarbon groups, R1 saturated aliphatic hydrocarbon groups with a chain of 4 to 20 carbon atoms at least one being branched, R6 methyl or ethyl groups, and R7 saturated aliphatic hydrocarbon groups of 1 to 4 carbon atoms are the predominant proportion in compositions with a viscousity at 25 DEG C. of from 400 to 50,000 centipoises.  The esters are prepared by heating in the absence of an esterification catalyst and air, a saturated dicarboxylic acid H00C R1 COOH or a mixture of acids, at least one of which is a branched-chain acid e.g. 2-ethyl-suberic acid, 2 : 5-diethyl, 2 : 2 : 4-trimethyl and 2 : 4 : 4-trimethyl adipic acids or a mixture of 72-80% -2-ethyl suberic acid, 12-18% 2 : 5-diethyl adipic acid and 6-10% sebacic acid known as iso-sebacic acid, a 2 : 2-dialkylene propylene glycol e.g. neopentyl glycol or 2-methyl-2-n-propyl-1 : 3-propane diol, and at least one monohydric alcohol e.g. 2-ethyl hexanol and 3 : 5 : 5 trimethyl hexanol.  In examples, iso-sebacic acid, 2-ethyl hexanol and neopentyl glycol; and iso-sebacic acid, 2-ethyl hexanol and 2-methyl-2 n-propyl-1 : 3-propane diol are heated together under nitrogen in two stages, of 1 hour up to 130 DEG C., and 7 hours from 130 to 200 DEG C., a further amount of diol added and the heating continued further at 200 DEG C., and then under vacuo at 200 DEG C. to acid value below 5 mgm KOM/gm. The compositions are used as synthetic lubricants, thickeners for saturated diester lubricants e.g. octyl nonyl sebacate and plasticisers for thermoplasts e.g. polyvinyl chloride.ALSO:Complex esters formed by reaction between dicarboxylic acids, glycols and monohydric alcohols and having the general formula: <FORM:0854673/III/1> , where n represents an average value of 1 or above, R represents saturated aliphatic hydrocarbon groups, R1 saturated aliphatic hydrocarbon groups with a chain of 4 to 20 carbon atoms at least one being branched, R6 methyl or ethyl groups, and R7 saturated aliphatic hydrocarbon groups of 1 to 4 carbon atoms, constitute the predominant ingredient in compositions with a viscosity at 25 DEG C. of from 450 to 50,0000 centipoises which may be used as lubricants or as thickeners for saturated diester lubricants, e.g. octyl monyl sebacate.  Reactants which may be employed in preparing the complex esters are (a) saturated dicarboxylic acids, or a mixture thereof, at least one of which is a branched chain acid, e.g. 2-ethyl suberic, 2:5-diethyl, 2:2:4-trimethyl, and 2:4:4-trimethyl adipic acids or a mixture of 72-80% 2-ethyl suberic acid, 12-18% 2:5-diethy adipic acid and 6-10% sebacic acid known as iso-sebacic acid, (b) a 2:2-dialkyl propylene glycol, e.g. neopentyl glycol or 2-methyl-2-n-propyl-1-3-propane diol, and (c) at least one monohydric alcohol, e.g. 2-ethyl hexanol and 3:5:5 trimethyl hexanol.