Patent GB-947910-A (GB)
Title: Surface active ethers of n-(hydroxymethyl)-lactams
IPC: C07D211/76
Filed: 1961-10-17
Abstract: The invention comprises non-foaming alkalistable surface active ethers of N-(hydroxymethyl)-lactams of the general formula: <FORM:0947910/C2/1> wherein R is an alkyl group of 8 to 18 carbon atoms or a phenyl or naphthyl group substituted by 1 or 2 alkyl groups of from 8 to 18 carbon atoms; R1 is hydrogen or methyl and wherein the ethoxy and propoxy units are arranged in any order when both are present in the -OCH2CHR1 chain; R2; R3 and R4 are hydrogen, methyl or ethyl radicals; z is a single bond, -CH2-, -CH2-CH2- or -o- and m is an integer of from 2 to 100.  The ethers may be prepared by reacting polyethoxylated or polypropoxylated phenols or aliphatic alcohols or mixed polyglycol monoether of phenol or aliphatic alcohols with an N-(hydroxymethyl)-lactam at a temperature of 80 DEG C. for 4 to 12 hours in the presence of p-toluene sulphonic acid monohydrate and neutralising the reaction mass with an organic amine. The phenol or aliphatic alcohol may be polyethoxylated or polypropoxylated in situ and the N-(hydroxymethyl) lactam may be prepared by reacting alkyl substituted or unsubstituted 2-pyrrolidone, a -piperidone, caprolactam or morpholone with p-formaldehyde in the presence of potassium hydroxide. Several examples are given. U.S.A. Specifications 1,970,578, 2,213,477, 2,575,832, 2,593,112 and 2,676,975 are referred to.ALSO:The invention comprises non-foaming alkali stable surface active ethers of N-(hydroxymethyl)-lactams of the general formula: <FORM:0947910/C3/1> wherein R is a C8 to C18 alkyl group or a phenyl or naphthyl group substituted by 1 or 2 C8 to C18 alkyl groups, R1 is hydrogen or methyl, and wherein the ethoxy and propoxy units are arranged in any order when both are present in the -OCH2CHR1 chain, R2, R3 and R4 are hydrogen, methyl or ethyl radicals, Z is a single bond, -CH2-, -CH2-CH2- or -O- and m is an integer of from 2 to 100.  The ethers may be prepared by reacting polyethoxylated or polypropoxylated phenols or aliphatic alcohols or mixed polyglycol monoether of phenol or aliphatic alcohols with an N-(hydroxymethyl)-lactam at a temperature of 80 DEG C. for 4 to 12 hours in the presence of p-toluene sulphonic acid monohydrate and neutralising the reaction mass with an organic amine.  The phenol or aliphatic alcohol may be polyethoxylated or polypropoxylated in situ. Several examples are given. U.S.A. Specifications 1,970,578, 2,213,477, 2,575,832, 2,593,112 and 2,676,975 are referred to.ALSO:Surface-active ethers of N-(hydroxymethyl)-lactams of the general formula <FORM:0947910/C3/1> wherein R is a C8 to C18 alkyl group on a phenyl or naphthyl group substituted by 1 or 2 C8 to C18 alkyl groups, R1 is hydrogen or methyl and wherein the ethenoxy and propenoxy units are arranged in any order when both are present in the -OCH2CHR1- chain, R2, R3 and R4 are hydrogen, methyl or ethyl radicals, 2 is a single band, -CH2-, -CH2-CH2-, or -O- and m is an integer of from 2 to 100, may be mixed with alkali metal hydroxides or silicates to yield non-discoloring and non-foaming surface active compositions.  Such compositions are suitable for cleaning metals prior to plating, fabricating and processing, and for washing glass, dishes and bottles.  U.S.A. Specifications 1,970,578, 2,213,477, 2,575,832, 2,593,112 and 2,676,975 are referred to.