Patent GB-575134-A (GB)
Title: Vulcanizable polymerization products
IPC: C08K5/16
Filed: 1943-10-14
Abstract: A condensation product of a ketone and an aliphatic amine is added to rubber, natural or synthetic, or to a synthetic resin to increase its softness and surface tackiness.  The preferred products are condensates of aliphatic ketones with aliphatic primary amines containing a hydroxy, or another primary amino substituent in the b position.  Suitable ketones are acetone diacetone alcohol, mesityl oxide, phorone, isophorone, methyl ethyl ketone, acetophenone, benzophenone, diethyl ketone, dibutyl ketone, methyl isopropyl ketone, diisopropyl ketone, dibenzyl ketone, benzoyl acetone, hydracetyl acetone, monochloroacetone, dichloro acetone, aldol acetone, ethylidene acetone, allyl acetone, furfural acetone, formaldehyde acetone, hydroxy benzal acetone, hydroxy acetone, cyclopentanone, cyclohexanone, and amines specified are ethanol amine, isopropanol amine, hydroxyethyl ethylenediamine, ethylene diamine, ethylene triamine, n-butyl amine, ethyl amine, 2-amino 1-butanol.  The condensation may be effected by heat in the presence of a catalyst such as iodine, sulphuric acid, hydrochloric acid, aluminium chloride, zinc chloride, hydriodic acid, hydrobromic acid, bromine, benzene sulphonic acid, p-toluene sulphonic acid.  In an example, dry acetone vapour is passed for 56 hours through a mixture of 122 parts of monoethanolamine and 16 parts of crude benzene sulphonic acid heated to 110-130 DEG  C.  Unreacted constituents are removed by distillation under reduced pressure until the vapour temperature reaches 96 DEG  C. at 5 mm. pressure. The catalyst is removed by digesting with caustic soda.  The products have a softening effect on natural rubber, particularly at a slightly raised temperature, but their effect is most marked on sulphur vulcanizable polymers which normally lack softness and surface tackiness, such as copolymers of butadiene-1,3 and vinyl compounds.  5 per cent is a suitable addition.  These compounds also possess antioxidant and polymerization inhibiting properties.  Specifications 466,346 and 550,651 are referred to.ALSO:A condensation product of a ketone and an aliphatic amine is added to rubber, natural or synthetic, or to a synthetic resin to increase its softness and surface tackiness.  The preferred products are condensations of aliphatic ketones with aliphatic primary amines containing a hydroxy, or another primary amino substituent in the b -position.  Suitable ketones are acetone, diacetone alcohol, mesityl oxide, phorone, isophorone, methyl ethyl ketone, acetophenone, benzophenone, diethyl ketone, dibutyl ketone, methyl isopropyl ketone, diisopropyl ketone, dibenzyl ketone, benzoyl acetone, hydracetyl acetone, monochloroacetone, dichloro acetone, aldol acetone, ethylidene acetone, allyl acetone, furfural acetone, formaldehyde acetone, hydroxy benzal acetone, hydroxy acetone, cyclopentanone, cyclohexanone, and amines specified are ethanol amine, isopropanol amine, hydroxy ethyl ethylene diamine, ethylene diamine, ethylene triamine, m-butyl amine, ethyl amine, 2-amino-1-butanol.  The condensation may be effected by heat in the presence of a catalyst such as iodine, sulphuric acid, hydrochloric acid, aluminium chloride, zinc chloride, hydriodic acid, hydrobromic acid, bromine, benzene sulphonic acid, p-toluene sulphonic acid.  In an example, dry acetone vapour is passed for 56 hours through a mixture of 122 parts of monoethanolamine and 16 parts of crude benzene sulphonic acid heated to 110-130 DEG  C.  Unreacted constituents are removed by distillation under reduced pressure until the vapour temperature reaches 96 DEG  C. at 5 mm. pressure.  The catalyst is removed by digesting with caustic soda.  The products have a softening effect on natural rubber, particularly at a slightly raised temperature, but their effect is most marked on sulphur vulcanizable polymers which normally lack softness and surface tackiness, such as copolymers of butadiene-1,3, and vinyl compounds. 5 per cent is a suitable addition.  These compounds also possess antioxidant and polymerization inhibiting properties.  Specifications 466,346 and 550,651, [both in Group IV], are referred to.