Patent GB-500033-A (GB)
Title: Manufacture of capillary-active compounds
IPC: D06M13/438
Filed: 1937-04-27
Abstract: 500,033. Wetting &c. agents; making emulsions. GROVES, W. W. (I. G. Farbenindustrie Akt.-Ges.) April 27, 1937, No. 30006/38. Divided out of 499,879. Samples furnished. [Classes 2 (iii) and 15 (ii)] [Also in Group III] Products stated to have wetting, levelling and emulsifying properties, suitable for use, e.g. in mercerizing and dyeing in the textile, leather and paper industries are prepared by treating with alkylating and/or acylating agents which cause the products to be soluble in water, compounds having the formula RXR1XR2 wherein R and R2 are alkyl, cycloalkyl, alkaryl, or aralkyl radicles which together do not contain more than 24 carbon atoms but contain in each radicle at least one aliphatic chain of 3 or more carbon atoms, X is a sulphonamide, a urethane, or a urea group and R1 is an aliphatic radicle carrying at least one OH, NH2 or NH group. The alkylating and acylating agents either contain or react with the starting materials to form groups which impart solubility to the products.. Groups which cause solubility are the sulphuric acid ester and other inorganic polybasic acid ester groups, the sulphonic, carboxylic, quaternary ammonium, betaine, oxyalkyl and poly(oxyalkyl)groups. When the starting materials contain a hydroxy group they are rendered water soluble by treating them with sulphonating agents, suphocarboxylic acids or their halides, e.g. sulphoaceticacidchloride and sulphobenzoic acid chloride, organic halogensulphonic acids, e.g., benzylchloridesulphonic acid and #-chlorpropanedisulphonic acid, anhydrides of polybasic carboxylic acids, e.g. those of maleic, phthalic, diglycollic or thioglycollic acid, halogencarboxylie acids, e.g. bromsuccinic acid or with alkylene oxides. The products obtained when halogen carboxylic or sulphonic acids are used may be converted into betaines. The hydroxy group may also be reacted first with phosgene and then with an amino acid such as sarcosine, methyltaurine, albumin degradation products or methylghicamine. When the starting materials contain an amino or imino group they are treated with sulphonating agents, halogenalkyl or halogenaralkyl sulphonic acids, polycarboxylic acids or alkylene oxides. The amino group may also be converted into the carbamic acid chloride or isocyanate and then condensed with amino acids, hydroxy acids or potyhydroxy compounds such as sugars. Solubility may also be effected by converting the amino compounds into quaternary ammonium compounds. The compounds containing two sulphonamide groups are prepared by treating aliphatic hydroxy or amino disulphonic acids, e.g. #-hydroxypropane-alpha : gamma-disulphonic acid and #-aminopropane-alpha : gamma-disulphonic acid with amines such as butylamine, octylamine,dodecylmethylamine, dicyclohexylamine, octylaniline and amines derived from naphthenic and resinic acid. Polyamines and polyaminoalcohols such as 1 : 3-diaminohydroxypropane, diethylenetriamine may be reacted with sulphonic acids to give the required starting materials. Butylsulphonic acid, hexyltoluenesulphonic acid and isododecylbenzene sulphonic acid are mentioned. Compounds containing two urea residues are prepared by reacting amines, in the form of their isocyanates or carbamic acid chlorides with aliphatic polyamino or polyamino hydroxy compounds. Thus alpha-ethylhexylisocyanate may be treated with di(methylamino)hydroxypropane. Compounds containing two urethane residues are prepared by causing carbamic acid chlorides or isocyanates of amines to react with aliphatic polyhydroxyamines or at least trihydric polyalcohols, e.g. glycerine, trimethylolpropane, mannitol, triethanolamine, 1 : 3-dihydroxyaminopropane and dimothylglucamine. The products may. be employed in association with soap, mucilage, glue, soluble cellulose derivatives, starch, bentonite, butanol, xylenylglycol, Glauber's salt, soda, sodium pyro and meta phosphates, trisodium phosphate, sodium perborate and sodium hypochlorite. Samples have been furnished under Sect. 2 (5) of products prepared as follows : (1) di(dodecylureido-#-ethyl)amine, obtained from dodecylisocyanate and diethylenetriamine is reacted with diglycollicanhydride and also with ethylene oxide ; (2) diethylenetriamine is reacted with a mixture of isocyanates derived from fatty acids produced by the oxidation of paraffin and the resulting diureide made soluble by treatment with sodium monoohloracetate; (3) the diureide obtained from n-octylisocyanate and 1 : 3-diammo-2-hydroxypropane is sulphonated ; (4) propanesulphochloride is condensed with 1 : 3-diamino-2-hydroxypropane and the resulting disulphonamide treated with ethyleneoxide ; (5) a diurethane obtained from alpha-ethylhexyl chlorformic ester and alpha : gamma-diamino-#-hydroxypropane is treated with chlorsulphonic acid.