Patent GB-657419-A (GB)
Title: Improvements relating to the production of fatty polyamides
IPC: D06M13/02
Filed: 1948-02-27
Abstract: Mixed fatty polyamides derived from polyamines acylated with a carboxylic acid containing 8-22 carbon atoms and a carboxylic acid containing 2-5 carbon atoms (for preparation see Group IV (b)) may be added to viscose spinning baths to prevent clogging of the spinnerettes.ALSO:Mixed fatty polyamides are obtained by reacting a polyamine of formula <FORM:0657419/IV (b)/1> wherein n is a whole number, R3 is hydrogen or an alkylol radical and R4 and R5 is hydrogen or alkyl radicals with a fatty acid containing from 8 to 22, preferably 12 to 18, carbon atoms or an ester thereof and with a fatty acid containing from 2 to 5 carbon atoms or an ester, anhydride or acid halide thereof.  Amines specified are ethylene diamine, diethylene triamine, triethylene tetramine, tetraethylene pentamine, and hydroxy ethyl ethylene diamine, diethylene triamine being preferred.  It is preferred that the polyamide contains a secondary amino group for then solubility may be enhanced by treatment with weak acids, e.g. acetic and lactic acids, preferably by mixing a dilute aqueous solution of the acid with the molten polyamide, stirring until homogeneous, cooling and recovering the amide.  When polyamines containing more than three nitrogen atoms are prepared it is preferred that sufficient amounts of short chain fatty acid are used to acylate all but one of the secondary amino groups.  Long chain acids specified are caprylic, nonylic, capric, undecylic, lauric, myristic, palmitic, stearic, behenic, oleic and ricinoleic acids or mixtures thereof and as esters glycerides are mentioned and preferred to the free acid.  Glycerides specified are teaseed, castor and hydrogenated castor oils.  Short chain acids specified are acetic, glycollic, lactic, propionic, butyric or valeric acids. Acetic acid or anhydride is preferred.  Preferably the long chain acid is first reacted with the polyamine although when using di- or triamines the short chain acid may be the first to be reacted.  The long chain acid is reacted in equimolar proportions with the polyamine at approximately 120 DEG  to 200 DEG  C., preferably 150-170 DEG  C. generally for about 8 hours.  The pressure is preferably atmospheric although other pressures may be used.  If a glyceride, e.g. coconut oil is used in place of the acid then approximately one-third mol. of the glyceride is used per mol. of polyamine. The monoamide is then mixed with the required amount of short chain acid or said derivative thereof and reaction effected at atmospheric or other pressure and at approximately 135 DEG  C. for about 3 to 5 hours when the temperature is raised to 150 DEG  to 170 DEG  C. for about 5 to 8 additional hours.  If desired, the free NH2 group may be completely acylated and the NH group adjacent the long chain fatty group may also be acylated. Generally the number of mols. of short chain acid employed per mol. of polyamine will be equivalent to the number of groups to be acylated.  In examples in which reactions are effected at preferred temperatures acetic anhydride is used in each case in the second stage, the first stage being reactions between diethylene triamine and (1) and (2) coconut oil, (6) teaseed oil, (7) oleic acid, (8) palmitic acid, (9) lauric acid, and (10) stearic acid, and coconut oil is reacted with (3) tetraethylene pentamine, (4) ethylene diamine, and (5) hydroxy ethyl ethylene diamine, the products of all but (1), (4) and (5) being further treated with 3 per cent acetic acid by the method described above so as to increase their solubility in water.  In the Specification as open to inspection under Sect. 91 the amines to be used may contain ether, keto, imino, neutralized imino, hydroxyl and amide groups in the portion of the molecule between the amino groups and an acid chloride of the long chain acid may be used.  Many other polyamines are specified, e.g. sym. diamino ethyl ether, 1,6-diamino hexane and particularly those containing hydroxy groups such as ethanol propylene diamine, 1-amino-3-methyl amino isopropanol and 1 - amino - dimethyl - 5 - methylaminodimethyl n-pentanol-3.  In examples ethylene diamine is reacted with (11) hydrogenated tallow and glycollic acid, and (12) oleic acid and acetic anhydride, (13) sym. diethyl ethylene diamine is reacted with stearic acid and lactic acid, ethanol ethylene diamine is reacted with (14) hydrogenated soyabean oil and acetic acid, (15) stearic acid and acetic anhydride, (16) oleic acid and acetic anhydride, (17) refined corn oil and acetic anhydride, (18) lauric acid chloride and glyceric acid and (19) oleic acid and glycollic acid and in (20) 1,3-diamino isopropanol is reacted with stearic acid and acetic anhydride.  This subject-matter does not appear in the Specification as accepted.ALSO:Textile softeners and wetting and dispersing agents comprise mixed fatty polyamides derived from polyamides acylated with a carboxylic acid containing 8-22 carbon atoms and a carboxylic acid containing 2-5 carbon atoms (for preparation see Group IV (b)).  The polyamides are also stated to be of use in the preparation of detergents.  They may be applied to the material in the form of dilute solutions.  In the Specification as open to inspection under Sect. 91 an example (21) is given in which cotton sheeting is passed through a quetch containing a 1/4 per cent aqueous dispersion of a polyamide derived from ethanol ethylene diamine, coconut oil and acetic anhydride, the fabric having a smooth, soft and even handle when dried.  This subject-matter does not appear in the Specification as accepted.ALSO:Mixed fatty polyamides derived from polyamines acylated with a carboxylic acid containing 8-22 carbon atoms and a carboxylic acid containing 2-5 carbon atoms (for preparation see Group IV (b)) are lubricants for textiles and other fibrous materials and are used as defoamers and in the preparation of emulsifying agents.  In the Specification as open to inspection under Sect. 91, examples are given: (14) of an emulsifying agent obtained from hydrogenated soya bean oil, acetic acid and ethanol ethylene diamine; (17) of a water-in-oil emulsifying agent from refined corn oil, acetic anhydride and ethanol ethylene diamine; (22) an emulsion for waterproofing textiles is obtained by melting together paraffin wax and the amide of (14) and adding thereto aqueous aluminium acetate solution; (23) a condensation product derived from ethanol ethylene diamine, oleic acid and acetic anhydride is used to form a water-in-oil emulsion of mineral seal oil; (25) an emulsion is obtained from neats' foot oil, water and a hydroxy acetic acid solution of the product of (17); (18) the product of reaction between ethanol ethylene diamine, lauric acid chloride and glyceric acid is said to show excellent lubricating properties and that of (19) derived from the same amine, oleic acid and glycollic acid is said to have fibre lubricating properties.  This subject-matter does not appear in the Specification as accepted.ALSO:The Specification as open to inspection under Sect. 91 contains an example (23) of a lubricant for use in the moulding of ceramic materials comprising a water-in-oil emulsion of mineral seal oil, the emulsifying agent being a mixed fatty polyamide derived from ethanol ethylene diamine (1 mol.), stearic acid (1 mol.) and acetic anhydride ( 1/2 mol.). For the preparation of this and similar amides (see Group IV (b)). This subject-matter does not appear in the Specification as accepted.