Patent GB-892822-A (GB)
Title: Amidation products of oxidation products of paraffin hydrocarbons and process for their manufacture
IPC: C08G69/26
Filed: 1958-10-17
Abstract: Products suitable for protecting metals against corrosion containing amides and/or ester-amides are obtained by reacting a crude air oxidation product of a paraffin hydrocarbon having a solidification point above 60 DEG C. and in which at least 80% by weight of said paraffin hydrocarbon is converted into oxygen containing derivatives (i.e. carboxylic acids, esters, alcohols and ketones), with at least one amine containing two primary amino groups or one primary amino group and in addition thereto one or more esterifiable hydroxyl groups.  The paraffin hydrocarbon may be admixed with up to 40% by weight of a polyethylene having a molecular weight below 20,000 prior to the oxidation step.  The crude oxidation product may be further oxidized with chromosulphuric acid or may be admixed with dicarboxylic acids or derivatives thereof, such as esters, acid halides or acid anhydrides prior to reaction with the amines. Specified amines are ethylene diamine, propylene diamine, butylene diamine, hexamethylene diamine, diaminocyclohexanes, 4:41-diamino-dicyclohexylmethane, benzidine, tolidine, dianisidine, 4:41, diamino-diphenylmethane, diethylene triaminedipropylene triamine, dibutylene triamine, ethanolamine, propanolamine, butanolamine, N-(hydroxyethyl)- and N:N-di(hydroxyethyl)-ethylene diamine, N-(hydroxyethyl)-and N:N-di(hydroxyethyl)-propylene diamine, N-hydroxyethyl-benzidine and mono- and di-(hydroxyethyl)-aminobenzene.  Specified dicarboxylic acids which may be admixed with the oxidation product prior to amidation are succinic, maleic, glutaric, adipic, sebacic, phthalic, isophthalic, terephthalic, and cyclohexyl-para-dicarboxylic acids, di-phenoxy-acetic acid dimethylmethane di-phenoxy-butyric acid dimethyl methane, resorcinol-diacetic acid and benzidine-diacetic acid.ALSO:The invention comprises products suitable for protecting metals against corrosion containing amides and/or ester-amides obtainable by reacting a crude air oxidation product of a paraffin hydrocarbon having a solidification point above 60 DEG C. and in which at least 80% by weight of said paraffin hydrocarbon is converted into oxygen containing derivatives (i.e. carboxylic acids, esters, alcohols and ketones) with at least one amine containing two primary amino groups or one primary amino group and in addition thereto one or more esterifiable hydroxyl groups.  The paraffin hydrocarbon may be admixed with up to 40% by weight of a polyethylene having a molecular weight below 20,000 prior to the oxidation step. The crude oxidation product may be further oxidized with chromosulphuric acid or may be admixed with dicarboxylic acids or derivatives thereof, such as esters, acid halides or acid anhydrides prior to reaction with the amines. Specified amines are ethylene diamine, propylene diamine, butylene diamine, hexamethylene diamine, diamino-cyclohexanes, 4:41-diamino-dicyclohexylmethane, benzidine, tolidine, dianisidine, 4:41-diamino-diphenylmethane, diethylene triamine, dipropylene triamine, dibutylene triamine, ethanolamine, propanolanime, butanolamine, N-(hydroxyethyl)- and N:N-di(hydroxyethyl)-ethylene diamine, N-(hydroxyethyl)- and N:N-di (hydroxyethyl)-propylene diamine, N-hydroxyethyl-benzidine and mono- and di(hydroxyethyl)-aminobenzene.  Specified dicarboxylic acids which may be admixed with the oxidation product prior to amidation are succinic, maleic, glutaric, adipic, sebacic, phthalic, isophthalic, terephthalic, and cyclohexyl-para-dicarboxylic acids, di-phenoxy-acetic acid dimethylmethane, di-phenoxybutyric acid dimethyl methane, resorcinol-diacetic acid and benzidine-diacetic acid.ALSO:The invention comprises products containing amides and/or ester-amides obtainable by reacting a crude air oxidation product of a paraffin hydrocarbon having a solidification point above 60 DEG C. and in which at least 80% by weight of said paraffin hydrocarbon is converted into oxygen containing derivatives (i.e. carboxylic acids, esters, alcohols and ketones) with at least one amine containing two primary amino groups or one primary amino group and in addition thereto one or more esterifiable hydroxyl group.  The paraffin hydrocarbon may be admixed with up to 40% by weight of a polyethylene having a molecular weight below 20,000 prior to the oxidation step. The crude oxidation product may be further oxidized with chromosulphuric acid or may be admixed with dicarboxylic acids or derivatives thereof, such as esters, acid halides or acid anhydrides prior to reaction with the amines. Specified amines are ethylene diamine, propylene diamine, butylene diamine, hexamethylene diamine, diamino-cyclohexanes, 4 : 41-diamino-dicyclohexylmethane, benzidine, tolidine, dianisidine, 4 : 41-diaminodiphenylmethane, diethylene triamine, dipropylene triamine, dubutylene triamine, ethanolamine, propanolamine, butanolamine, N-(hydroxyethyl)- and N : N-di(hydroxyethyl)-ethylene diamine, N-(hydroxyethyl)- and N : N-di(hydroxyethyl)-propylene diamine, N-hydroxyethyl-benzidine and mono- and di-(hydroxyethyl)-aminobenzene.  Specified dicarboxylic acids which may be admixed with the oxidation product prior to amidation are succinic, maleic, glutaric, adipic, sebacic, phthalic, isophthalic, terephthalic and cyclohexyl-para-dicarboxylic acids, di-phenoxy-acetic acid dimethylmethane, di-phenoxy-butyric acid dimethyl methane, resorcinol-diacetic acid and benzidine-diacetic acid.