Patent GB-854963-A (GB)
Title: Complex esters and process for their manufacture
Inventor: CRITCHLEY STUART WALTER
IPC: C08G63/16
Filed: 1958-05-23
Abstract: Polyesters of general formula : HO[CH2,C(R6) <FORM:0854963/IV(a)/1> where n represents an average value of 1 or above, R1 represents saturated aliphatic hydrocarbon groups with a chain of 4-20 carbon atoms, R6 methyl or ethyl groups and Rn saturated aliphatic hydrocarbon groups of 1 to 4 carbon atoms, provided that where R6 and R7 each represents a methyl group at least one of the R1's is a branched-chain and which have a viscosity of at 25 DEG C. of 1,000 to 500,000 centipoises, may be used as plasticizers for thermoplasts such as polyvinyl chloride.  They are prepared by heating in the absence of air a saturated, aliphatic dicarboxylic acid or acids of general formula HOOCR1COOH e.g. 2-ethyl suberic acid, 2 : 5 diethyl, 2 : 2 : 4 trimethyl or 2 : 4 : 4-trimethyl adipic acids and a 2 : 2-dialkylpropylene glycol e.g. neopentyl glycol or 2-methyl-2-n-propylene-1 : 3 propane diol the molecular proportion of the glycol being greater than that of the total carboxylic acid. When a 2 : 2-dialkyl propylene is used at least one of the acids is a branched-chain acid.  A mixture of one or more branched chain aliphatic dicarboxylic acids and one or more saturated straight chain aliphatic dicarboxylic acids such as sebacic acid may be used, e.g. a mixture of 72-80% 2-ethylsuberic acid, 12-18% diethyladipic acid and 6-10% sebacic acid, known as iso-sebacic acid, and an equimolecular mixture of 2 : 4 : 4-trimethyladipic acid, 2 : 4 : 4 trimethyl adipic acid and sebacic acid.  In Examples (1) isosebacic acid and 2 : 2-dimethyl-1 : 3- propanediol with and without sebacic acid; sebacic acid and 2-methyl-2-n-propyl-1 : 3-propanediol; and sebacic acid and 2 : 2-diethyl-1 : 3-propanediol are heated under nitrogen in stages. 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:Polyesters of general formula:  HO[CH2.C(R6) (R7) CH2 OOCR1COO]n CH2C(R6) (R7) CH2OH where n represents an average value of 1 or above, R1 represents saturated aliphatic hydrocarbon groups with a chain of 4-20 carbon atoms, R6 methyl or ethyl groups and R7 saturated, aliphatic hydrocarbon groups of 1 to 4 carbon atoms, provided that where R6 and R7 each represents a methyl group, at least one of the R1'S is branchedchain, and which have a viscosity at 25 DEG C of 1,000 to 500,000 centipoises are prepared by heating in the absence of an esterification catalyst and of air a saturated, aliphatic dicarboxylic acid or acids of general formula HOOC. R1.COOH, e.g. 2-ethylsuberic acid, 2:5-diethyladipic, 2:2:4 trimethyladipic or 2:4:4-trimethyladipic acids and a 2:2-dialkylpropylene glycol, e.g. neopentyl glycol or 2-methyl-2-n-propyl-1:3-propane diol the molecular proportion of the glycol being greater than that of the total carboxylic acid. When a 2:2-dialkyl propylene is used at least one of the acids is a branched-chain acid.  A mixture of one or more branched-chain aliphatic dicarboxylic acids and one or more saturated straight chain aliphatic dicarboxylic acids such as sebacic acid may be used, e.g. a mixture of 72-80% 2-ethylsuberic acid, 12-18% diethyladipic acid and 6-10% sebacic acid known as isosebacic acid, and an equimolecular mixture of 2:2:4-trimethyladipic acid, 2:4:4-trimethyladipic acid and sebacic acid.  In examples (1) isosebacic acid and 2:2-dimethyl-1:3-propanediol with and without sebacic acid; sebacic acid and 2-methyl-2-n-propyl-1:3-propanediol; and sebacic acid and 2:2-diethyl-1:3-propanediol are heated under nitrogen in stages. The products are useful as synthetic lubricants, thickeners for saturated diesters used as lubricants and plasticisers for thermoplasts such as polyvinylchloride.ALSO:Polyesters of general formula: HO[CH2.C(R6)(R7)CH2OOCR1COO]n CH2C(R6)(R7)CH2OH where n represents an average value of 1 or above, R1 represents saturated aliphatic hydrocarbon groups with a chain of 4-20 carbon atoms, R6 methyl or ethyl groups and R7 saturated aliphatic hydrocarbon groups of 1 to 4 carbon atoms, provided that where R6 and R7 each represents a methyl group at least one of the R1's is a branched chain, which polyesters have a viscosity at 25 DEG C. of 1000 to 500,000 centipoises, may be used as lubricants or thickeners for saturated diester lubricants. The esters are prepared by heating in the absence of air a saturated aliphatic dicarboxylic acid or acids of general formula HOOCR1.COOH, e.g. 2-ethyl ruberic acid, 2:5-diethyl, 2:2:4-trimethyl, or 2:4:4-trimethyl adipic acids and a 2:2-dialkylenepropylene glycol, e.g. neopentyl glycol or 2-methyl-2-n-propyl-1:3 propane diol, the molecular proportion of the glycol being greater than that of the total carboxylic acid. When a 2:2-dialkyl propylene glycol is used, at least one of the acids is a branched chain acid.  A mixture of one or more branched chain, aliphatic dicarboxylic acids, such as sebacic acid, may be used, e.g. a mixture of 72-80% 2-ethyl-ruberic acid, 12-18% diethyl-adipic and 6-10% sebacic acid, known as iso-sebacic acid, and an equimolecular mixture of 2:4:4-trimethyladipic acid, 2:4:4-trimethyl adipic acid and sebacic acid.