Patent GB-657422-A (GB)
Title: Manufacture of new amide derivatives
IPC: D06M13/402
Filed: 1948-03-16
Abstract: Amide derivatives are obtained by reacting at least one mol. of an alkylene oxide, e.g. ethylene oxide or glycide with one mol. of a condensation product containing the atomic grouping <FORM:0657422/IV (a)/1> and having at least one reactive hydrogen atom, which is obtained by reacting a carboxylic acid amide having at least one hydrogen atom bound to the amide nitrogen atom, formaldehyde and an oxyalkylamine, or by reacting a N-methylol derivative of such an acid amide with an oxyalkylamine.  The oxyalkylamines may be primary, secondary or tertiary amines, e.g. mono-(di- or tri-)-ethanolamine tripropanolamine, tributanolamine, butyl-diethanolamine or di-(oxyethyl)-cyclohexylamine.  It is preferred to react the alkylene oxide with condensation products obtainable from a carboxylic acid amide containing at least eight carbon atoms, e.g. a high molecular weight fatty acid, a resin acid or a naphthenic acid, formaldehyde and a tertiary oxyalkylamine.  Two to twenty mols. and preferably 2 to 3 mols. of the alkylene oxide may be reacted with 1 mol. of the condensation product and the reaction is preferably effected at 100-180 DEG  C.  A substance having an alkaline reaction may be added as catalyst, e.g. an alkali metal hydroxide or an alkali metal salt of an organic carboxylic acid such as sodium acetate or an alkali metal such as sodium may be added as catalyst.  The products of the invention in the form of their salts with aliphatic acids of low molecular weight and in many cases in the form of the free bases are soluble in water and can be used as textile assistants, softening agents and as agents for preventing the agglomeration of fibrils in the manufacture of staple fibres of regenerated cellulose (see Group IV (c)).  The products may also be used as wetting, dispersing or levelling agents.  Specification 600,707, [Group IV (c)], is referred to.ALSO:Amide derivatives are obtained by reacting at least one mol. of an alkylene oxide with one mol. of a condensation product containing the atomic grouping <FORM:0657422/IV (b)/1> and having at least one reactive hydrogen atom, which is obtainable by reacting a carboxylic acid amide having at least one hydrogen atom bound to the amide nitrogen atom, formaldehyde and an oxyalkylamine, or by reacting a N-methylol derivative of such an acid amide with an oxyalkylamine.  By "reactive hydrogen atom" is meant a hydrogen atom bound to nitrogen or oxygen.  The oxyalkylamines may be primary, secondary or tertiary amines, e.g. mono-(di- or tri-) ethanolamine, and it is preferred to use condensation products obtainable from a carboxylic acid amide containing at least eight carbon atoms, e.g. a high molecular weight fatty acid, a resin acid or a naphthenic acid, formaldehyde and a tertiary oxyalkylamine.  Such products may be made by the method disclosed in Specification 600,707, e.g. from a higher p  fatty acid amide containing at least 12 carbon atoms, e.g. the amide of lauric acid, coconut oil fatty acid, palmitic, stearic, oleic or linoleic acids, formaldehyde and a tertiary oxyalkylamine such as triethanolamine, tripropanolamine, tributanolamine, butyl-diethanolamine or di-(oxyethyl)-cyclohexylamine.  The amide may be reacted with formaldehyde to form the N-methylolamide and the latter then reacted with the tertiary oxyalkylamine, e.g. by heating at 100-140 DEG  C., preferably under reduced pressure and in the presence of sodium carbonate.  Specified alkylene oxides are ethylene oxide and glycide and the reaction with the alkylene oxide is preferably effected at 100-180 DEG  C. and in the case of ethylene oxide the reaction may be effected at atmospheric or superatmospheric pressure.  A substance having an alkaline reaction may be added as catalyst, e.g. an alkali metal hydroxide or an alkali metal salt of an organic carboxylic acid such as sodium acetate or an alkali metal such as sodium may be added as catalyst.  One mol, or more than one mol. of alkylene oxide, e.g. 2 to 20 mols. and preferably 2-3 mols. may be reacted with a mol. of the condensation product.  In examples: (1), (4) and (5) the condensation product of the formula R-CO-NH-CH2-O-CH2-CH2-N(CH2 -CH2-OH)2 in which RCO is the acyl residue of commercial stearic acid (obtainable by heating commercial stearic acid N-methylolamide with triethanolamine at 100-111 DEG  C. under reduced pressure with the addition of sodium carbonate and removing water, e.g. by means of benzene) is heated to 130 DEG  C. and then sodium is added in small portions.  Ethylene oxide is then introduced at 130-140 DEG  C. and at atmospheric pressure to yield a product which is a soft or wax-like mass; (2) a condensation product obtainable from oleic acid N-methylolamide and triethanolamine in a manner similar to that in (1) is dehydrated, e.g. by means of benzene and after beating to 90 DEG  C. sodium is added.  Ethylene oxide is then introduced at 90-95 DEG  C. to yield a liquid product; (3) a mixture of the initial condensation products of (1) and (2) are reacted with ethylene oxide as in (2) to yield a soft mass; (6) an initial condensation product similar to that used in (1) is heated to 130 DEG  C. and gaseous ethylene oxide then introduced at 130-140 DEG C., the condensation product is prepared by converting commercial stearic acid to the N-methylolamide derivative by means of paraformaldehyde and then the product is heated with triethanolamine and anhydrous sodium carbonate under reduced pressure.  The products of the invention in the form of their salts with aliphatic acids of low molecular weight and in many cases in the form of the free bases are soluble in water and can be used as textile assistants, softening agents and as agents for preventing the agglomeration of fibrils in the manufacture of staple fibres of regenerated cellulose (see Group IV (c)).  The products may also be used as wetting, dispersing or levelling agents.  The Specification as open to inspection under Sect. 91 states that the initial condensation product which is reacted with the alkylene oxide is obtainable from a sulphonic acid amide as well as from a carboxylic acid amide.  This subject-matter does not appear in the Specification as accepted.ALSO:Amide derivatives made by reacting at least one mol. of an alkylene oxide, e.g. ethylene oxide or glycide, with one mol. of a condensation product containing the atomic grouping <FORM:0657422/IV (c)/1> and having at least one reactive hydrogen atom, which is obtainable by reacting a carboxylic acid amide having at least one hydrogen atom bound to the amide nitrogen atom, formaldehyde and an oxyalkylamine, or by reacting a N-methylol derivative of such an acid amide with an oxyalkylamine, (see Group IV (b)) can be used as textile assistants, e.g. in the form of their salts with aliphatic acids of low molecular weight.  The products which contain an aliphatic or cycloaliphatic residue of at least 12 carbon atoms can be used as wetting or dispersing agents and as softening agents and are especially valuable as agents for preventing the agglomeration of fibrils in the manufacture of staple fibres of regenerated cellulose.  For the latter purpose water-soluble mixtures of sulphonated oils, e.g. sulphonated olive or castor oil with the amide products which contain an aliphatic residue of at least 12 carbon atoms and especially of 16-18 carbon atoms are suitable.  Other substances customarily used with textile assistants may also be present.  In examples: (1) a product suitable for vivifying staple fibres of regenerated cellulose is obtained by adding water to the product obtained by reacting ethylene oxide with the condensation product R-CO-NH-CH2-O-CH2-CH2-N(CH2 -CH2-OH)2 in which R-CO- represents the acyl residue of commercial stearic acid (see Group IV (b)) and mixing the paste so obtained with 2 parts of ordinary commercial Turkey red oil; (2) chlorinated wool is softened by working the material at a liquor ratio of 1 : 20 in a bath heated to 20 DEG  C. and containing the mixture containing Turkey red oil used in (1). Specification 600,707 is referred to.