Patent GB-836566-A (GB)
Title: Phthalidyl ethers of polyglycols
Filed: 1957-04-26
Abstract: The invention comprises phthalidyl ethers of polyglycols having a molecular weight no greater than 10,000, due to the polyglycol portion thereof, and having the general formula <FORM:0836566/IV (b)/1> and phthalidyl ethers of polyglycol ethers having a molecular weight no greater than 10,000 due to the total polyglycol portion and having the general formula <FORM:0836566/IV (b)/2> wherein each Z represents an alkyleneoxy group -CnH2nO-, n being an integer from 2 to 4, X represents H or chlorine, x is an integer of at least 2, R represents the residue of a monohydric phenol or a mono- or poly-hydric saturated aliphatic alcohol and y represents the valency of the phenol or alcohol.  The term "glycol portion" denotes the structure -O(CnH2nO)x-. The ethers may be prepared by reacting phthalaldehydic acid with the appropriate polyglycol or polyglycol ether using a proportion of acid sufficient to react with all the hydroxyl groups present in the glycol compound.  Temperatures of 50-250 DEG  C. are used at pressures from 5 to 760 mms.  Stabilizers and anti-oxidants such as p,p1-isopropylidene diphenol may be present. The product may be washed with water and then mixed with benzene and the latter distilled off to remove water and volatile impurities. The phthalidyl ethers may be used as lubricants, blending and thickening agents, textile treating agents and plasticizers (see Group IV (a)); some of the ethers show parasiticidal activity. Examples include the preparation of (1) the bisphthalidyl ethers of dipropylene glycol, a polypropylene glycol 256 and a polybutylene glycol (M.W. about 500); (2) phthalidyl ethers of various methyl, ethyl, isopropyl, butyl and octyl monoethers of di-, tri- and higher polyethylene and polypropylene glycols; (3) the bischlorophthalidyl ether of polypropylene glycol 256.  Other examples include the preparation of phthalidyl ethers of high molecular weight polyalkylene, including ethyleneoxy propyleneoxy glycols, mono-ethers thereof and of trihydroxy polyetheneoxy-propyleneoxy ethers of glycerol (see Group IV (a)). Specifications 779,981 and 836,567 are referred to.ALSO:The invention comprises phthalidyl ethers of polyglycols having a molecular weight no greater than 10,000 due to the polyglycol portion thereof and having the general formula <FORM:0836566/IV (a)/1> and phthalidyl ethers of polyglycol ethers having a molecular weight no greater than 10,000 due to the total polyglycol portion thereof and having the general formula <FORM:0836566/IV (a)/2> wherein each Z represents an alkyleneoxy group -CnH2nO-, n being an integer from 2 to 4, X represents hydrogen or chlorine, x is an integer of at least 2, R represents the residue of a monohydric phenol or a mono- or polyhydric saturated aliphatic alcohol and y represents the valency of the phenol or alcohol.  The term "glycol portion" denotes the structure -O(CnH2nO)x-.  The oxyalkylene chains in the ethers may contain from 2 to 200 or more alkyleneoxy units.  The ethers may be prepared by reacting phthalaldehydic acid with the appropriate polyglycol or polyglycol ether using sufficient acid to react with all hydroxyl groups present in the glycol reagent.  Temperatures of from 50-250 DEG  C. are used at pressures from 5 to 760 mms.  Stabilizers and antioxidants such as p,p1-isopropylidene diphenol may be present.  The product may be washed with water and then dehydrated and purified by adding benzene and thereafter distilling off the solvent.  The products are preferably derived from glycols obtained from ethylene oxide, 1 : 2-propylene oxide, 1 : 2- and 2 : 3-butylene oxides and mixtures thereof.  The phthalidyl ethers are useful as lubricants, blending and thickening agents, plasticizers and textile treating agents and some show parasiticidal activity.  Examples describe the preparation of (1) phthalidyl ethers of various methyl, ethyl, isopropyl, butyl, octyl and phenyl mono ethers of polyethylene glycols and polypropylene glycols; (2) bis-phthalidyl ethers of polyethylene, polypropylene, polyethylenepropylene, and polybutylene glycols; (3) trisphthalidyl ethers of tri-hydroxy (polyethyleneoxy-propyleneoxy)ethers of glycerol; and (4) the bis-chlorophthalidyl ether of a polypropylene glycol.  The phthalidyl ethers of polyglycols having molar weights of from 400-1000 may be used to plasticize vinyl lacquer films.  Thus a vinyl chloride-vinyl acetate polymer may be plasticized with tripropylene glycol isopropyl phthalidyl ether containing p,p1 - isopropylidene diphenol as stabilizer.  Specification 669,644, 779,981 and 836,567 are referred to.