Polyglycidyl ethers of polyphenols

摘要

Polyglycidyl ethers are produced by reacting polyphenols having the structure Ar1-CH2-Ar-CH2-Ar1 wherein Ar is an arylene group, and each Ar1 is an aryl group containing at least two phenolic hydroxyl groups, with epichlorohydrin in the presence of an excess of a base such as caustic soda. It is generally desirable to utilize an amount of epichlorohydrin which is from 2 to 20 times the equivalent of the hydroxyl groups of the polyphenol. As the amount of the epichlorohydrin approaches equivalency, the chain-length and viscosity of the polyglycidyl ether increases. The polyglycidyl ethers, after removal of excess epichlorohydrin, are usually very viscous or solid materials; but they can be readily liquified by heating. The molten polyglycidyl ethers may be hardened to provide epoxy resins of good heat-distortion characteristics by means of a curing agent, such as an amine, acid anhydride, polyamide or sulphone. In Example 1, the tetraphenol is heated to about 100 DEG C. with 32 equivalents of epichlorohydrin; and sodium hydroxide (4 equivalents) is added over a period of 2 hours. The mixture is then maintained at 116 DEG C. for 5 hours. The mixture is filtered; and the excess epichlorohydrin is removed by distillation under reduced pressure. The polyglycidyl ether so obtained may be cured by adding methylene dianiline, chlorendic acid anhydride or diamino diphenyl sulphone.ALSO:Polyglycidyl ethers are produced by reacting polyphenols having the structure Ar1-CH2-Ar-CH2-Ar1 wherein Ar is an arylene group, and each Ar1 is an aryl group containing at least two phenolic hydroxyl groups, with epichlorohydrin in the presence of an excess of a base such as caustic soda. Polyphenols of the above type are produced by reacting 1 mol of a bis(halomethyl)substituted aromatic hydrocarbon with 2 mols of a polyphenol Ar1H. In example C, resorcinol is reacted with 1,4-bis-(chloromethyl)-benzene to give the tetraphenol In Example IV, the above tetraphenol is heated with epichlorohydrin and caustic soda to form predominantly the polyglycidyl ether of the formula In example A, bis-(1,3-dihydroxyphenylmethyl)-m-xylene is obtained by reacting resorcinol with 4,6 - bis - (chloromethyl) - m - xylene; and in Example I the tetraphenol is reacted with epichlorohydrin. Polyphenols may also be prepared by reacting catechol, hydroquinone, pyrogallol, phloroglucinol, p,p1-isopropylidenediphenol, or tetrachloro-p,p1-isopropylidenediphenol, or alkylated derivatives thereof, with the bis-(chloromethyl) derivatives of benzene, toluene, xylene or mesitylene. The polyglycidyl ethers may be hardened to produce epoxy resins (Group IV(a)).