Patent GB-808561-A (GB)
Title: Substitution products of polymerised olefins
IPC: C07C17/10
Filed: 1955-06-21
Abstract: The invention comprises a polymerized olefin having from 9 to 16 carbon atoms in the polymerized olefinic group and having as a substituent or substituents at least one but not more than two chlorine atoms or not more than one chlorine atom and an omega-aminoalkylamino group interrupted by at least one imino group, and mixtures of such polymerized olefins; and the preparation thereof by treating the unsubstituted polymerized olefin with hypochlorous acid or with chlorine in the substantial absence of actinic light, the temperature not exceeding 25 DEG  C., until at least one but not more than two chlorine atoms have been introduced and, when the nitrogen-containing products are required, heating the chlorinated compounds with an alpha:omega-alkylene diamine in which the alkylene chain is interrupted by at least one imino group.  Preferably the polymer is a trimer, tetramer or pentamer of propylene.  The chlorination may be effected with elementary chlorine in the presence of a solvent which is subsequently distilled off or with hypochlorous acid, which may be formed in situ from, for example, sodium hypochlorite and hydrochloric acid, in the absence of a solvent, the resulting mixture being allowed to separate into two layers and the top layer being washed, dried and distilled to give the required product.  The temperature in all these processes preferably does not exceed 10 DEG  C.  It is stated that the reactive chlorine atom in the products is believed to be attached to the main carbon chain and not to one of the carbon atoms participating in the double bond.  The alkylene diamine used in the second stage is preferably a polyethylene polyamine and preferably at least two molecular proportions of alkylene diamine are used for each molecular proportion of chlorine-substituted olefin.  The chlorination processes are described in general terms and a table showing the results obtained using olefins of differing average carbon atom content (varying from C12 to C16) differing molar proportions of chlorine (varying from 1.0 to 2.0) and differing temperature ranges is given, these results being given in terms of the weight increase per mol. of olefin, refractive index and percentage of chlorine, hypochlorous acid, preformed or formed in situ, being used in all these examples.  In a further example, an alkenyl chloride prepared by reacting a propylene tetramer with hypochlorous acid formed in situ, is refluxed with diethylenetriamine, the mixture is allowed to settle and the top layer is distilled at 165 DEG  C. under 45 mm. absolute pressure to leave the required product as residue.  A second table shows the results obtained using olefins of differing average carbon atom content (varying from C12 to C16), differing molar proportions of chlorine (varying from 1.0 to 1.6), differing amines (additional amines are triethylene tetramine and tetraethylene pentamine) and differing mols. of amine per mol. of chloride (varying from 3.0 to 1 to 3.2 to 1), the results being given in terms of the refractive indices of the products.  The nitrogen-containing products are stated to have desirable properties as surface reacting agents.