Patent GB-510318-A (GB)
Title: Manufacture of substances of capillary action
IPC: D06P1/647
Filed: 1938-01-25
Abstract: 510,318. Making emulsions. GROVES, W. W. (I. G. Farbenindustrie Akt.-Ges.). Jan. 25, 1938, No. 2383. [Class 1 (i)] [Also in Group IV] Amines having the general formula (R. R1. R2) CN (R3. R4) wherein R and R1 stand for aliphatic hydrocarbon radicles each containing at least three carbon atoms and together containing at least eight carbon atoms and R2, R3 and R4 stand for hydrogen or organic radicles are rendered water soluble by treating them as follows : (a) by treatment with polybasic inorganic acids, their halides or anhydrides or with aminosulphonic acid, e.g., oleum, sulphuric anhydride, chlorsulphonic acid, potassium chlorsulphonate, sodium fluorsulphonate, phosphoric anhydride, phosphorous anhydride, boric acid and boric anhydride. (b) by treatment with organic halogen sulphonic acids, e.g., bromethanesulphonic acid,' benzylchloride sulphonic acid, chlorhydroxypropanesulphonic acid, #-chlorpropane disulphonic acid, chloracetonesulphonic acid : (c) by treatment with aldehyde or ketone sulphonic acids with subsequent hydrogenation ; acetaldehydedisulphonic acid, acetone mono- and disulphonic acids and benzaldehydesulphonic acid may be used and the products after hydrogenation converted into sulphobetaines by treatment with methylchloride, dimethylsulphate, benzyl chloride, ethyleneoxide or sodium butylsulphate : (d) by treatment with polybasic carboxylic acids, e.g., oxalic, succinic, maleic, diglycollic, sulphophthalic and sulphosuccinic acids : (e) by treatment with, halogencarboxylic acids or their salts, esters or amides, e.g., chloraceticacidmethyl ester, #-chlorproprionic acid, bromsuccinic acid and if desired converting the products into betaines by treatment with ethylbromide, ethyleneoxide, benzylchloride or sodium butylsulphate : (f) by converting them into quaternary ammonium compounds : (g) by treatment with alkylene oxides or chlorhydrins in the presence of alkali metal oxides or hydroxides, tin tetrachloride or aluminium chloride: mixtures of ethylene oxide with propylene oxide, glycide, epichlorhydrin or glycerolchlorhydrin may be used and the products may be condensed with halogensulphonic or carboxylic acids or with polybasic inorganic acids : (h) by treatment with phosgene and reacting the resulting isocyanates or carbamic acid chlorides with amino acids such as sarcosine, methyltaurine, albumin decomposition products, aminopolyhydroxy compounds or hydroxysulphonic acids; hydroxyethanesulphonic acid and methylglucamine may be used for this purpose : (i) by converting them into sulphonic or carboxylic acid amides followed by sulphonation when a sulpho group is not present ; sulphoacetic, sulphopropionic, sulphosuccinic, sulphobenzoic, sulphophthalic, glycollic, hydroxyethoxyacetic, lactic, glyceric, crotonic and benzoic acids and benzenesulphochloride may be used for this process : (j) converting them into aminocarboxylic acids by reaction with formaldehyde and hydrocyanic acid followed by saponification. The products are stated to be useful as emulsifying agents and may be used in association with soap, mucilage, glue, soluble cellulose derivatives, starch, bentonite, saponine, solvents such as butanol or xylenylglycol, sodium carbonate, Glauber's salt, sodium meta- and pyrophosphate, trisodiumphosphate, sodium perborate and sodium hypochlorite. In examples : (1) a mixture of amines prepared from the ketones derived from palm kernel acid by hydrogenating in the presence of liquid ammonia and a nickel catalyst is treated with ethylene oxide : (2) a mixture of primary amines prepared from the ketones derived from paraffin carboxylic acids by hydrogenating in the presence of ammonia is treated with : (a) diglycollic anhydride: (b) chlorsulphonic acid : (c) benzoic acid followed by sulphonation: (d) crotonic acid followed by sulphonation : (e) ethylene oxide ; the products are suitable for emulsifying mineral or olive oil: or (f) glycollic acid followed by sulphonation : (3) a mixture of amines prepared from the ketones derived from paraffin carboxylic acid by hydrogenating in the presence of ethanolamine is sulphonated : (4) 10-aminononadecane is converted , into its chloracetamide and the chlorine exchanged by treating with sodium sulphite : (5) 10-aminononadecane, 12-aminotricosane and 5-aminononadecane are condensed with glycollic acid and sulphonated : (6) 9-aminoheptadecane is treated with sodium bisulphite and formaldehyde and the product, after reaction with sodium cyanide saponified with caustic soda ; the resulting amino carboxylic acid is converted into a betaine by means of dimethyl sulphate : (7) the primary amines used in example (2), dissolved in methanol are hydrogenated in the presence of paraformaldehyde and the resulting mixture of tertiary amines treated with benzylchloride or with brom- or chloracetic-acid ethyl ester : (8) 10-amino nonadecane is treated with ethyleneoxide and converted into a quaternary ammonium salt by means of dimethylsulphate : (9) 8-aminotricosane is reacted with dimethylsulphate : (10) 6-aminotricosane is converted into 6-dimethylaminotricosane by the process used in Example 7 and the latter product reacted with chloracetic acid ethyl ester and saponified : (11) 4-aminoheptadecane is condensed with (a) sodium sulphoacetate : (b) propyleneoxide and dimethylsulphate and then sulphonated and (c) phosgene and metanilic acid : (12) 10-aminononadecane is converted into the isocyanate and reacted with sodium n-butyltaurine or sodium propyl-, isobutyl-, isohexyl, hydroxyethyl- or #-ethylhexyltaurine. The following components are also specified : 7-amino tridecane, 8-amino-pentadecane, 8- amino-5 : 7-diethylpentadecane, 9-hydroxyethylaminoheptadecane,9-methylaminoheptadecane, 8-benzylaminopentadecane, amines obtained from ketones by hydrogenating them in the presence of ammonia or amines, and amines obtained from suitable halogenated hydrocarbons by reaction with ammonia or amines. Ketones suitable for conversion into amines may be prepared from acids such as caprylic, capric, lauric, palmitic and #-ethylhexylic acid, carboxylic acids obtained by the oxidation of paraffin or by treating the mixtures obtained by the catalytic hydrogenation of carbon oxides with alkali, the carboxylic acids obtained by treating carbon mono- or dioxide with steam in the presence of an olefine and possibly hydrogen and the carboxylic acids derived from halogenated hydrocarbons by saponifying the corresponding nitriles.