Patent GB-500550-A (GB)
Title: Manufacture of condensation products suitable for wetting, dispersing and like purposes
IPC: C09K23/00
Filed: 1937-08-06
Abstract: 500,550. Wetting &c. agents. GROVES, W. W. (I. G. Farbenindustrie Akt.-Ges) Aug. 6, 1937, No. 21710. [Classes 2 (iii) and 15 (ii)] Condensation products are manufactured by reacting aliphatic polyhydroxy compounds (including polyhydroxy amines) in the presence of water or an organic solvent with a chloromethyl compound of the general formula where Ar stands for an aromatic hydrocarbon radicle, which may contain further substituents, R1 and R2 each stands for an alkyl radicle of at least three carbon atoms, an aralkyl radicle or a cycloaliphatic hydrocarbon radicle, or R1 has the aforesaid meaning and R2 stands for hydrogen, and X stands for a hydroxy group or hydrogen, and, if desired, treating the products with polybasic inorganic acids containing oxygen, or with functional derivatives thereof, e.g. sulphuric acid, fuming sulphuric acid, chlorosulphonic acid, the halides of phosphorus, or phosphorus pentoxide. Suitable chloromethyl compounds are those obtainable from aromatic hydroxy compounds <R>1R2>Ar-OH by the action of formaldehyde and concentrated hydrochloric acid while passing dry hydrogen chloride through the mass, or those obtainable from alkylated, cycloalkylated or aralkylated aromatic hydrocarbons or substitution products thereof by the action of formaldehyde and concentrated hydrochloric acid, e.g. iso-tert. butyl-, isohexyl-, and isooctylbenzyl chlorides, isooctyl-o-methylbenzyl chlorides, p-n-dodecylbenzyl chloride, p-octodecylbenzyl chlorides, dodecylchloromethylnaphthalenes, p - cyclohexylbenzyl chloride, diisobutylbenzyl chlorides, and the chloromothyl compounds from the condensation products of chlorinated aliphatic hydrocarbons of high molecular weight or of olefines obtained by dimerization of isobutylene isohexylene or isoheptylene or by polymerization of propylene, with aromatic hydrocarbons. Suitable polyhydroxy compounds are glycerol, polyglycerols, erythritol, pentaerythritol, trimethylolpropane, hexitols, e.g. mannitol and sorbitol, polyhydroxy compounds obtained by reduction of condensation products of formaldehyde or by reduction cleavage of carbohydrates, monosaccharides, e.g. glucose, fructose and mannose, polysaccharides, e.g. saccharose, maltose and cellobiose, sugar mixtures obtained by hydrolysis of cellulose or by condensation of formaldehyde, and watersoluble dextrin-like degradation products of cellulose and starch, also polyhydroxy amines, e.g. triethanolamine, the reaction products of triethanolamine with ethylene oxide, diethanolamine, propandiolamines, glucamine, methylglucamine, phenylglucamine, diglucamine, and compounds obtained by hydrogenating the condensation products of formaldehyde or water-soluble degradation products of cellulose or starch in the presence of primary or secondary amines. Suitable organic solvents are aqueous or anhydrous alcohols, e.g. methyl, ethyl or butyl alcohol, dioxane, benzene and chloroform. The reaction may be accelerated by acid or basic condensation catalysts, e.g. alkali metal hydroxides, alcoholates, amides or carbonates, piperidine, diethylamine, inorganic acids such as hydrochloric or sulphuric acid, strong organic acids such as p-toluenesulphonic, chloracetic or lactic acid, and acid salts or salts forming complex compounds, e.g. zinc chloride, aluminium chloride or lithium bromide. The reaction solutions may be worked up by diluting them with water, extracting the unchanged chloromethyl compounds with water - insoluble solvents, e.g. ether, and evaporating the aqueous solution. The products may be used in the textile, paper and leather industries as wetting, dispersing, emulsifying or cleansing agents, e.g. in washing, fulling, carbonizing, mercerizing, kier-boiling, dyeing, and finishing, in softening artificial silk and in the treatment of hides and leather, for which purposes they may be employed alone or mixed with other substances, e.g. soaps, turkey red oils, sulphonic acids, organic compounds, salts such as perborates or phosphates, organic solvents such as cyclohexanol, tetrahydronaphthalene, benzyl alcohol, butanol or hydrocarbons, or glue, gelatine or gum-like substances. In examples, the following substances are heated together in aqueous alcoholic solution: (1) 2-chloromethyl-4-isooctylphenol and glucose, in the presence of sodium carbonate; (2) 2-chloromethyl-4-isooctylphenol and diglucamine, in the presence of sodium carbonate ; (3) 2-chloromethyl-4-isooctylphenol and methylglucamine, in the presence of sodium carbonate ; (4) the chloromethyl derivative of the alkylphenol formed by condensing dihexylene-diheptylene with phenol, and methylglucamine or diglucamine, in the presence of sodium carbonate ; (5) p-dodecylbenzyl chloride and methylglucamine ; (6) p-dodecylbcnzyl chloride and diglucamine ; (7) p-dodecylbenzyl chloride and diethanolamine, in the presence of sodium carbonate ; (8) 2-chloromothyl-4-cyclohexylphenol and glucose or methylglucamine, in the presence of sodium carbonate.