Patent GB-475867-A (GB)
Title: Manufacture of products of capillary action
Filed: 1936-04-22
Abstract: Isocyclic primary and secondary amines containing at least one aliphatic radicle with more than 3 carbon atoms in the nucleus are reacted with alkylene oxides or monohalogen compounds of polyhydric alcohols, the reaction of ethylene oxide or glycide with wholly or partly hydrogenated organic amino compounds comprising at least 2 carbon rings and 12 carbon atoms and containing a hydrogenated butylphenyl residue being excluded.  The products are useful as wetting and emulsifying agents in the textile and dyeing industries, for washing textile materials, skins and feathers, for greasing wool, particularly in combination with mineral oils, or olein and in combination with organic solvents in dry cleaning processes.  The products may be reacted with further quantities of alkylene oxides or monohalogen derivatives of polyhydric alcohols and also with halogen carboxylic acids, halogen alkyl sulphonic acids, polybasic carboxylic acids, sulphonic acids, phosgene to give chlorcarbonic esters or formaldehyde and hydrochloric acid to give chlormethylethers.  The chlorcarbonic esters may be treated with oxyalkylsulphonic acids, aminoalkylsulphonic acids, aminoarylsulphonic acids or aminoalkyl or aminoaryl carboxylic acids.  The chlormethylethers may be reacted with a tertiary base or with potassium cyanide and the products saponified.  The isocyclic amines containing at least one aliphatic radicle with more than 3 carbon atoms may be prepared by treating aromatic amines with alcohols or by nitration of alkylated aromatic hydrocarbons followed by reduction.  In examples: (1) ethylene oxide is reacted with isododecylaniline in the presence of sodium methylate; the product has foaming properties which may be improved by treatment with methylchloride, dimethylsulphate, or benzylchloride; ethylene oxide is also reacted with a dodecylaniline which is prepared by condensing a chlorinated middle oil with benzene in the presence of a metal or metallic salt as catalyst followed by nitration and reduction; the product is finally condensed with sodium chloracetate; (2) propyleneoxide is reacted with 2-methoxy-5-a  : a <1> : d  : d <1>-tetramethylbutylaniline which may be obtained by condensing phenol with diisobutylene in the presence of aluminium chloride or borontrifluoride followed by methylation, nitration and reduction; the product is finally heated with diglycollic anhydride; (3) 2 - methoxy - 5 - isobutylaniline is condensed with glycide; the product may be methylated or acetylated; 2-methoxy-5-isobutylcyclohexylamine, obtainable by catalytic hydrogenation of 2-methoxy-5-isobutyl aniline, may be similarly treated; (4) ethylene oxide is reacted with 2-methoxy-5-octyl - 1 : 3 - phenylenediamine, 2 - methoxy-5-octylcyclohexylamine, 2-amino-4-octylphenol, 1 - ethylamino - 4 - nonylbenzene, iso - dodecylaniline, 4 - hexyl - 2 - aminotoluene, aminoisononyldiphenyl (prepared by condensing diphenyl with a propylenepolymerizate in the presence of borofluoride - phosphoric acid followed by nitration and reduction) and with 4 - isooctyl - 2<1> - aminodiphenylether (prepared by condensing o-chlornitrobenzene with sodium p-isooctylphenolate followed by reduction); (5) 4-octyl-2-eminonaphthalene is reacted first with ethylenechlorhydrin and then with ethylene oxide; (6) propylene oxide is reacted with dodecylaniline and the product treated with phosgene in the presence of pyridine to give a chlorcarbonic ester; the latter is condensed with sodium taurin, sodium methyl taurin, sodium sarcosin, sodium metanilate, amino acids obtained from albumins or with sodium oxyethane sulphonate; (7) iso hexyl tetrahydronaphthylamine is treated with 1 : 2-butylene oxide or the latter is treated with an alkylated naphthylamine obtained by condensing a chlorinated petroleum fraction with naphthalene, nitrating and reducing the product; (8) p-butyl aniline is condensed with ethylene chlorhydrin and the product treated with maleic acid; (9) stearoyl aniline, obtained by nitration of stearoylbenzene followed by reduction is reacted with glycide and the product converted into a quaternary ammonium salt by means of dimethylsulphate; (10) propyleneoxide is reacted with iso-butyl phenylenediamine which may be obtained by condensing benzene with isobutylene, dinitration and reduction; the product may be treated with dimethylsulphate to obtain a product suitable for washing wool.ALSO:Isocylic primary and secondary amines containing at least one aliphatic radicle with more than 3 carbon atoms in the nucleus are reacted with alkyleneoxides or monohalogen compounds of polyhydric alcohols.  The products, which are stated to be emulsifying p  agents, are useful for greasing wool, particularly in combination with mineral oils or olein, and in combination with organic solvents may be used in dry cleaning processes.  The products may be reacted with further quantities of alkylene oxides or monohalogen derivatives of polyhydric alcohols and also with halogen carboxylic acids, halogen alkyl sulphonic acids, polybasic carboxylic acids, sulphonic acids, phosgene to give chlorcarbonic esters, or formaldehyde and hydrochloric acid to give chlormethylethers.  The chlorcarbonic esters may be treated with oxyalkylsulphonic acids aminoalkylsulphonic acids, aminoarylsulphonic acids or aminoalkyl or aminoaryl carboxylic acids.  The chlormethylethers may be reacted with a tertiary base or with potassium cyanide and the products saponified.  In examples: (1) ethylene oxide is reacted with isododecylaniline in the presence of sodium methylate; the product may be treated with methylchloride, dimethylsulphate, or benzylchloride; ethylene oxide is also reacted with a dodecylaniline which is prepared by condensing a chlorinated middle oil with benzene in the presence of a metal or metallic salt as catalyst followed by nitration and reduction; the product is finally condensed with sodium chloracetate: (2) propyleneoxide is reacted with 2-methoxy-5-a  : a <1> : d  : d <1> - tetramethylbutylaniline; the product is heated with diglycollic anhydride: (3) 2-methoxy-5-isobutylaniline is condensed with glycide; the product may be methylated or acetylated; 2-methoxy-5-isobutylcyclohexylamine may be similarly treated: (4) ethylene oxide is reacted with 2-methoxy-5 octyl-1 : 3-phenylenediamine, 2-methoxy-5-octylcyclohexylamine, 2-amino-4-octylphenol, 1-ethylamino-4-nonylbenzene, iso-dodecylaniline, 4-hexyl-2 aminotoluene, aminoisononyldiphenyl and with 4-isooctyl-2<1>-aminodiphenylether: (5) 4-octyl-2-aminonaphthalene is reacted first with ethylenechlorhydrin and then with ethylene oxide: (6) propylene oxide is reacted with dodecylaniline and the product treated with phosgene in the presence of pyridine to give a chlorcarbonic ester; the latter is condensed with sodium taurin, sodium methyl taurin, sodium sarcosin, sodium metanilate, amino acids obtained from albumins or with sodium oxyethane sulphonate: (7) isohexyl tetrahydronaphthylamine is treated with 1 : 2 butyleneoxide or the latter is treated with an alkylated naphthylamine obtained by condensing a chlorinated petroleum fraction with naphthalene, nitrating and reducing the product: (8) p-butylaniline is condensed with ethylene chlorhydrin and the product treated with maleic acid: (9) stearoyl aniline is reacted with glycide and the product converted into a quaternary ammonium salt by means of dimethylsulphate: (10) propyleneoxide is reacted with iso butyl phenylenediamine; the product may be treated with dimethylsulphate.