GB851536A - Preparation of rubbery interpolymer derivatives - Google Patents

Abstract

Rubber derivatives of a solid interpolymer of 70-90% of a isoolefin containing 4 to 8 carbon atoms and a terminal methylene group copolymerized with 1-30% of a polyolefinic hydrocarbon containing 4 to 8 carbon atoms are made by dry-mixing said interpolymer with 1-25 parts per 100 parts of interpolymer of (1) an N-bromo-N-chloro hydantoin of the formula: <FORM:0851536/IV(a)/1> wherein either R may be hydrogen or an alkyl radical and when R is an alkyl radical at least one R contains from 1 to 8 carbon atoms and one X is bromine and the other X is chlorine or (2) a mixture of an N-bromohydantoin of the above formula wherein R is a defined as above and where one X is bromine and the other is bromine or hydrogen and an N-chlorohydantoin of the above formula where R is as defined above and where one X is chlorine and the other is chlorine or hydrogen, said mixture containing said N-bromo-hydantoin in amount substantially equivalent to 90-40% of N,N1-dibromo-5,- dimethyl hydantoin and said N-chloro-hydantoin in amount substantially equivalent to 10-60% of N,N1-cichlori-5,5-dimethyl hydantoin, and then heating the hydantoin-interpolymer mixture above 170 DEG F. The isoolefin may be isobutylene, 3-methyl butene-1, 4-methyl pentene-1, 2-ethyl butene-1, 4-ethyl pentene-1 or a mixture of such isoolefins. The polyolefin may be butadiene, isoprene, dimethallyl, cyclopentadiene, a triolefin e.g. fulvene, a tetraolefin or mixtures thereof. The isoolefin-polyolefin interpolymer may also contain other interpolymerized monomers such as styrene, chlorostyrenes, alkyl styrenes, or acrylyl or methallyl acid chloride. The interpolymers preferably contain from 1 to 5 mol per cent unsaturation. The N-bromo-N-chlor hydantoin may be the 5,5-dimethyl, the 5-methyl-5-ethyl or 5-methyl -5-isobutyl alkyl derivatives. The N-bromo-hydantoin may be N-bromo- 5,5-dimethyl or -5-methyl-5-ethyl hydantoin or 1-3-dibromo-5,5-dimethyl -5-methyl-5-ethyl or -5-methyl-5-isobutyl hydantoin or 1,3-dibromohydantoin. The N-chloro-hydantoin may be N-chloro-5,5-dimethyl or -5-methyl-5-ethyl hydantoin or 1,3-dichlorohydantoin or 1,3 dichloro-5,5-dimethyl, -5-methyl-5-ethyl or -5-methyl-5-isobutyl hydantoin. The halohydantoins may be mixed with the interpolymers in the presence of compounding ingredients such as carbon black and finely divided silica. The interpolymer-halohydantoin derivatives may be formed into compositions with calcium silicate stabilizer, natural rubber, alkylated arylamine antioxidant, carbon black, zinc oxide, petroleum base softener, benzothiazyl disulphide, diorthotolyl guanidine and sulphur and these compositions may be vulcanized. Specifications 701,453 and 739,610 are referred to.