Patent GB-857156-A (GB)
Title: Alkylphenoxypolyethoxyalkanols and method of preparation thereof
IPC: C08G65/28
Filed: 1957-11-25
Abstract: Polyoxyalkylene compounds of formula:  <FORM:0857156/IV(a)/1> where R is an alkyl group of 8 or 9 carbon atoms, A is an alkylene chain of 3 or 4 carbon atoms, n is 7-16 and m is 1-10, are obtained by reacting nonyl or octyl phenol first with ethylene oxide and then with propylene oxide or butylene oxide or a mixture thereof at 130-210 DEG C. in the presence of a strong basic catalyst. The octyl and nonyl radical may be normal, iso or tertiary and may occupy any position in the benzene ring the para position being preferred.  The value of n must be at least 1,2 and preferably about 2 to 3 times the value of m where A is propylene and must be at least 4 where m is butylene.  The polymers are liquids having good detergency and wetting properties, high cloud points, little foaming tendency and low solidification temperatures.  In Examples (1) 103 parts octyl phenol and 5 parts sodium are heated at 175 DEG C. in a vessel flushed with nitrogen. 213,4 parta ethylene oxide are introduced over a period of 2 hours. The adduct is washed with water, neutralised with 10% hydrochloric acid and then made basic with sodium hydroxide.  The adduct is then dissolved in isopropanol and sodium methylate is added. Propylene oxide is then added over a period of 5 hours at 140-179 DEG C. until three equivalents are reacted.  The compound obtained after washing and purification is C8H17C6H4(OC2H4)9,7 (OC3H6)3OH.  Lists of polyoxylalkylene derivatives of nonyl and octyl phenols prepared according to the p  invention are given.  Specification 739,266 is referred to.ALSO:Polyoxyalkylene compounds of formula : <FORM:0857156/IV(b)/1> where R is an alkyl group of 8 or 9 carbon atoms, A is an alkylene chain of 3 or 4 carbon atoms, n is 7-16 and m is 1-10, are obtained by reacting nonyl or octyl phenol first with ethylene oxide and then with propylene oxide or butylene oxide or a mixture thereof at 130 DEG  C.-210 DEG  C. in the presence of a strong basic catalyst.  The octyl and nonyl radical may be normal, iso or tertiary and may occupy any position in the benzene ring the para position being preferred.  The value of n must be at least 1,2 and preferably about 2 to 3 times the value of m where A is propylene and must be at least 4 where m is butylene.  The polymers are liquids having good detergency and wetting properties, high cloud points, little foaming tendency and low solidification temperatures.  In examples (1) 103 parts octyl phenol and 5 parts sodium are heated at 175 DEG  C. in a vessel flushed with nitrogen.  213,4 parts ethylene oxide are introduced over a period of 2 hours.  The adduct is washed with water, neutralised with 10% hydrochloric acid and then made basic with sodiumhydroxide.  The adduct is then dissolved in isopropanol and sodium methylate is added.  Propylene oxide is then added over a period of 5 hours at 140 DEG  C.-179 DEG  C. until three equivalents are reacted.  The compound obtained after washing and purification is C8H17C6H4(OC2H4) 9,7-(OC3H6)3OH.  Lists of polyoxylalkylene derivatives of nonyl and octyl phenols prepared according to the invention are given.  Specification 732,966 is referred to.