Patent GB-497939-A (GB)
Title: Improvements in retarding the oxidation of substances sensitive to oxidation
IPC: C10L1/24
Filed: 1937-06-28
Abstract: The oxidation of substances sensitive to oxidation is retarded by the addition of small amounts of compounds of the general formula <FORM:0497939/III/1> In the formula, R1 and R2 are hydrogen or an aliphatic, hydroaromatic, aromatic or heterocyclic radicle, which may be substituted in any way, or R1 and R2 together with the nitrogen atom may also be members of a heterocyclic ring; R3 is an aliphatic radicle, in particular an alkylene group which may also contain acyclic substituents; R4 is hydrogen or any other radicle which can be formed by substitution or salt-formation on the mercapto group or oxidation of the same to a disulphide, e.g. it can be as described for R1 and R2, or it may correspond to the group <FORM:0497939/III/2> , or it may be a metal.  The following compounds are mentioned as suitable: b -anilido-ethane-monothiol, bis-(b -mercapto-ethyl)-aniline, a (b -naphthylamino)-ethane-thiol, b -dodecyl-amino-propane-thiol, b -cyclohexylamino-b -methyl-ethane-thiol, piperidino-ethane-thiol, b -anilido-ethane-disulphide, bis-(b -anilido-ethyl)-thioether and b -anilido-ethane-lead-mercaptide.  The amounts used are generally less than 5 per cent of the substance to be protected.  In the examples: (1) a lubricating oil is protected by the use of b -anilido-ethane-thiol, a - or b -naphthylamino-ethane-thiol, bis-(b -methyl-b -mercapto-ethyl)-aniline, octodecylamino-isopropyl-thiol and cyclohexylamino-propane-thiol; (2) aniline is protected by anilido-ethane-thiol; (3) the oxidation of a mixture of chlorinated diphenyl and polymerized vinyl carbazole is retarded by anilido-ethane-thiol,; (4) the oxidation of the reaction product obtained by boiling an artificial resin with Chinese wood oil is inhibited by anilido-ethane-thiol; (5) anilido-ethane-thiol prevents the ageing of polymerized vinylisobutyl ether.  These substances are also used to retard the oxidation of fats and fatty oils mineral coal tar, natural and synthetic rubbers, synthetic resins in general, polymerization products of olefines, lacquers and films of cellulose derivatives and cellulose artificial masses, phenols, amines and varnishes.ALSO:The oxidation of substances sensitive to oxidation is retarded by the addition of small amounts of compounds of the general formula <FORM:0497939/IV/1> In the formula R1 and R2 are hydrogen or an aliphatic, hydroaromatic, aromatic or heterocyclic radicle, which may be substituted in any way, or R1 and R2 together with the nitrogen atom may also be members of a heterocyclic ring; R3 is an aliphatic radicle, in particular an alkylene group which may also contain acyclic substituents; R4 is hydrogen or any other radicle which can be formed by substitution or salt-formation on the mercapto group or oxidation of the same to a disulphide, e.g. it can be as described for R1 and R2, or it may correspond to the group <FORM:0497939/IV/2> , or it may be a metal.  The following compounds are mentioned as suitable: b -anilido-ethanemonothiol, bis-(b -mercapto-ethyl)-aniline, a (b -naphthylamino) - ethane - thiol, b  - dodecylamino - propane - thiol, b  - cyclohexylamino - b -methyl-ethane-thiol, piperidino-ethane-thiol, b  - anilido - ethane - disulphide, bis - (b  - anilidoethyl)-thioether and b -anilido-ethane-lead-mercaptide.  The amounts used are generally less than 5 per cent of the substance to be protected. In the examples: (1) a lubricating oil is protected by the use of b -anilido-ethane-thiol, a -or b  - naphthylamino - ethane - thiol, bis - (b -methyl-b -mercapto-ethyl)-aniline, octodecylamino - isopropyl - thiol and cyclohexylaminopropane-thiol; (2) aniline is protected by anilido-ethane-thiol; (3) the oxidation of a mixture of chlorinated diphenyl and polymerized vinyl carbazole is retarded by anilido-ethane-thiol; (4) the oxidation of the reaction product obtained by boiling an artificial resin with Chinese wood oil is inhibited by anilido-ethane-thiol; (5) anilido-ethane-thiol prevents the ageing of polymerized vinylisobutyl ether.  These substances are also used to retard the oxidation of fats and fatty oils, mineral coal tar, natural and synthetic rubbers, synthetic resins in general, polymerization products of olefines, lacquers and films of cellulose derivatives and cellulose artificial masses, phenols, amines, and varnishes.ALSO:The oxidation of substances sensitive to oxidation is retarded by the addition of small amounts of compounds of the general formula <FORM:0497939/V/1> In the formula R1 and R2 are hydrogen or an aliphatic hydroaromatic, aromatic or heterocyclic radicle, which may be substituted in any way, or R1 and R2 together with the nitrogen atom may also be members of a heterocyclic ring; R3 is an aliphatic radicle, in particular an alkylene group which may also contain acyclic substituents R4 is hydrogen or any other radicle which can be formed by substitution or salt-formation on the mercapto group or oxidation of the same to a disulphide, e.g. it can be as described for R1 and R2, or it may correspond to the group <FORM:0497939/V/2> , or it may be a metal.  The following compounds are mentioned as suitable: b -anilido-ethane-monothiol, bis-(b -mercapto-ethyl)-aniline, a (b -naphthylamino)-ethane-thiol, b -dodecyl-amino-propane-thiol, b -cyclohexylamino-b -methyl-ethane-thiol, piperidino-ethane-thiol, b -anilido-ethane-disulphide, bis-(b -anilido-ethyl)-thioether and b -anilido-ethane-lead-mercaptide.  The amounts used are generally less than 5 per cent of the substance to be protected.  In the examples: (1) a lubricating oil is protected by the use of b -anilido-ethane-thiol, a - or b -naphthyl-amino-ethane-thiol, bis-(b -methyl-b -mercapto-ethyl)-aniline, octodecylamino-isopropyl-thiol and cyclohexylamino-propane-thiol; (2) aniline is protected by anilido-ethane-thiol; (3) the oxidation of a mixture of chlorinated diphenyl and polymerized vinyl carbazole is retarded by anilido-ethane-thiol; (4) the oxidation of the reaction product obtained by boiling an artificial resin with Chinawood oil is inhibited by anilido-ethane-thiol; (5) anilido-ethane-thiol prevents the ageing of polymerized vinyl-isobutyl ether.  These substances are also used to retard the oxidation of fats and fatty oils, mineral coal tar, natural and synthetic rubbers, synthetic resins in general, polymerization products of olefines, lacquers and films of cellulose derivatives and cellulose artificial masses, phenols, amines, and varnishes.