Patent GB-738306-A (GB)
Title: Process for the preparation of basic nitrogenous condensation products
Filed: 1952-12-05
Abstract: A process for the preparation of basic nitrogenous condensation products is characterized by the feature that ethers of the formula RO-CH2-X wherein R is any aliphatic or hydroaromatic hydrocarbon radical containing at least 8 carbon atoms or any alkylated aromatic hydrocarbon radical containing at least one alkyl group with at least 5 carbon atoms, wherein the aliphatic hydrocarbon radical can be interrupted by heteroatoms and where X denotes the groups <FORM:0738306/IV (b)/1> are reacted with polyamines of the formula <FORM:0738306/IV (b)/2> wherein R1, R2, R3 and R4 denote hydrogen atoms, or alkyl or hydroxy alkyl or ether residues, A denotes zero or a whole number and wherein, if n should be zero, not all of R1, R2, R3 and R4 can be hydrogen atoms. The products can, if desired, be reacted with alkylating or aralkylating agents.  As ethers are specified octyl-, dodecyl-, hexadecyl-, octadecyl-, octadecenyl - oxy - propenoxides, alkylphenoxy - propenoxides and compounds of the general formula <FORM:0738306/IV (b)/3> wherein x denotes a whole number and R11 any hydrocarbon residue containing at least 8 carbon atoms, and/or the halogenohydrins corresponding to the above epoxides.  The halogenohydrins can be prepared by reacting the appropriate alcohols and phenols with glycerolepihalogenides, e.g. epichlorhydrin.  The epoxides are obtained by treating corresponding halogenohydrins with alkaline agents.  As polyamines there are specified diethylenetriamine, dipropylenetriamine, polyethylene and/or polypropylene polyamines, methylamino-ethylamine, 3 - isopropylamino - propylamine - 1, and 3.3-dimethylamino - propylamine - 1.  The products can be alkylated or converted into quaternary compounds by treatment with unsubstituted or substituted alkylating agents including e.g. hydroxyalkylating, carboxyalkylating and dialkylating agents such as ethylene oxide, dimethyl or diethyl sulphate, chloracetic acid, a  - chlor - b  - hydroxypropane - g  - sulphonic acid, or benzyl chloride.  Alkylation also includes the etherification of hydroxyl groups, e.g. with alkylene oxides. The products may be of the formula <FORM:0738306/IV (b)/4> where R1 and R11 denote radicals introduced by subsequent optional alkylation.  In examples of the preparation of condensation products (1) n-octylpropenoxide is reacted with diethylenetriamine and the product is reacted with ethylene oxide and then with dimethyl sulphate; (2) a similar reaction is effected using n-dodecylpropenoxide; (3) oleyloxypropenoxide is treated as in example (1); (4) iso-octyl phenoxypropenoxide is reacted with diethylene triamine to give a compound of the formula <FORM:0738306/IV (b)/5> which is reacted with 7 mols. of ethylene oxide and then with 3 mols. of dimethyl sulphate; (5) benzyl chloride is used in place of dimethyl sulphate in a process similar to (3); (6) equimolecular amounts of diethylenetriamine and a compound of the formula <FORM:0738306/IV (b)/6> are reacted.  Other polyalkylenepolyamines can be reacted similarly; (7) 1 mol. of oleyloxypropenoxide is reacted with excess diethylenetriamine, the excess is removed, and the product then reacted with 4 mols. of monochloracetic acid followed by 4 mols. of caustic soda to give on drying a powder of which the main constituent has the formula <FORM:0738306/IV (b)/7> (8) oleyloxypropenoxide and 3-isopropylaminopropylamine-1 are reacted in equimolecular amounts; (9) the product of example (8) is reacted with 2 mols. of ethylene oxide; (10) equimolecular amounts of oleyloxypropenoxide and dimethylaminopropylamine-1 are reacted; (11) n-octadecenyloxypropenoxide and diethylenetriamine are reacted, the product methylated with dimethyl sulphate and then treated with ethylene oxide; (12) n-octadecenyloxypropenoxide is reacted with 1.2 mols. of diethylenetriamine, then 7 mols. of ethylene oxide are reacted, and the ethoxylated compound is reacted with 2 mols. of epichlorhydrin; (13) tetraethylene pentamine is reacted with 2 mols. of n-octadecenyloxypropenoxide and then with 4.5 mols. of ethylene oxide; (14) n-octadecenyloxypropenoxide is reacted with 1.2 mols. of diethylenetriamine, then with 0.5 mol. of ethylene oxide, followed by 1 mol. the sodium salt of chloracetic acid; (15) one mol. of diamylphenoxypropenoxide is reacted with 1.5 mol. of diethylenetriamine, 7 mols. of ethylene oxide and 3 mols. of dimethyl sulphate; (16) n-octadecenyloxypropenoxide is reacted with 1 mol. of 3-dimethylaminopropylamine and then with 2 mols. of glycerol monochlorhydrin; (17) one mol. of the epoxide <FORM:0738306/IV (b)/8> (prepared from dodecylmercaptan, 2 mols. of ethylene oxide and 1 mol. of epichlorhydrin) is reacted with 1.2 mol. of diethylenetriamine; (18) one mol. of n-octadecenyloxypropenoxide is reacted with 1.1 mol. b -hydroxyethyl-ethylene diamine.  The product can be further treated with dimethyl sulphate.  The products are of use in dyeing processes, having levelling, penetrating and stripping action on substantive, acid, basic, chrome and vat dyestuffs.