Patent GB-871196-A (GB)
Title: Improvements relating to the stabilisation of organic material normally subject to oxidative deterioration
Inventor: GYSLING HERMANN DR
IPC: C09K23/00
Filed: 1958-06-13
Abstract: Organic materials normally subject to oxidative deterioration are stabilized by the addition of 0,001%-1,0% by weight of compounds of the formula:  <FORM:0871196/IV (a)/1> and/or <FORM:0871196/IV (a)/2> wherein Ar is an aryl or substituted aryl radical and R is hydrogen or an alkyl radical.  The organic materials may be polymers havingtertiary C atoms or unsaturated groups (e.g. polyethylene, polypropylene, and natural or synthetic polymers and copolymers of 1, 3-dienes such as rubber).  The radical Ar in the formulae may be phenyl, naphthyl or acenaphthenyl, and may carry substituents such as alkyl, cycloalkyl, aryl, aralkyl, trifluoromethyl, chlorophenyl, -SO2R (where R is alkyl, vinyl, benzyl or phenyl), -SO2NR1R2 (where R1 and R2 are alkyl, cyclohexyl or phenyl), sulphonic acid piperidide, esterified sulphonic acid, etherified hydroxyl, or cyano groups or halogen atoms.ALSO:Organic materials normally subject to oxidative deterioration are stabilized by the addition of 0,001-1,0% by weight of compounds of the formula:-  <FORM:0871196/IV (b)/1> and/or <FORM:0871196/IV (b)/2> wherein Ar is an aryl or substituted aryl radical and R is hydrogen or an alkyl radical.  The organic materials are hydrocarbons (especially motor fuels, mineral oils and mineral waxes), unsaturated fatty acids and esters thereof (such as fats, fatty oils and animal waxes), ethers, aldehydes, polymerisable unsaturated organic monomers (such as vinyl compounds and especially styrene) and polymers having tertiary C atoms or unsaturated groups (e.g. polyethylene, polypropylene, and natural or synthetic polymers and copolymers of 1,3-dienes such as rubber).  The radical Ar in the formulae may be phenyl, naphthyl or acenaphthenyl, and may carry substituents such as alkyl, cycloalkyl, aryl, aralkyl, trifluoromethyl, chlorophenyl, -SO2R (where R is alkyl, vinyl, benzyl or phenyl), -SO2NR1R2 (where R1 and R2 are alkyl, cyclohexyl or phenyl), sulphonic acid piperidide, esterified sulphonic acid, etherified hydroxyl, or cyano groups or halogen atoms.  In Examples, (i) 1-phenyl pyrazoline, 1-phenyl pyrazolidine, 1-(o-methoxy-phenyl)-pyrazoline, 1-(m-chlorophenyl)-pyrazoline, 1-p-tolyl-pyrazoline, 1-(p-tert. butyl-phenyl)-pyrazoline or 1-(p-tert. butyl-phenyl)-pyrazolidine is added to oenanthol, (ii) 1-phenyl pyrazoline is added to tetrahydronaphthalene or to tetrahydrofurane, (iii) 1-phenyl pyrazoline or 1-phenyl pyrazolidine is added to mineral lubricating oil, (iv) 1-phenyl-5-methyl-pyrazoline or 1-phenyl-5-methyl-pyrazolidine is added to nonaldehyde.  In some of the examples tests are described in which the antioxidants of the invention are compared with other antioxidants chosen from the following: - hydroquinone, 1-phenyl-3,5,5-trimethyl pyrazoline, 1-phenyl-3-isobutenyl-5,5-dimethyl pyrazoline and 1-phenyl-3-methyl-pyrazoline.ALSO:Organic materials normally subject to oxidative deterioration are stabilized by the addition of 0.001-1.0% by weight of compounds of the formula:- <FORM:0871196/III/1> and/or <FORM:0871196/III/2> wherein Ar is an aryl or substituted aryl radical and R is a hydrogen or an alkyl radical.  The organic materials may be hydrocarbons (especially motor fuels, mineral oils and mineral waxes) or unsaturated fatty acids or esters thereof (such as fats, fatty oils and animal waxes).  The radical Ar in the formulae may be phenyl, naphthyl or acenaphthenyl, and may carry substitutents such as alkyl, cycloalkyl, aryl, aralkyl, trifluoromethyl, chlorophenyl, -SO2R (where R is alkyl, vinyl, benzyl or phenyl), -SO2NR1R2 (where R1 an R2 are alkyl, cyclohexyl or phenyl), sulphonic acid piperidide, esterified sulphonic acid, etherified hydroxyl, or cyano groups of halogen atoms.  In an example, 1-phenyl pyrazoline or 1-phenyl pyrazolidine is added to mineral lubricating oil.ALSO:Animal and vegetable fats and fatty oils are stabilized against oxidative deterioration by the addition of 0,001-1,0% by weight of compounds of the formula <FORM:0871196/I/1> <FORM:0871196/I/2> wherein Ar is an aryl or substituted aryl radicle and R is hydrogen or an alkyl radicle.  The radicle Ar in the formulae may be phenyl, naphthyl, or acetnaphthenyl, and may carry substituents such as alkyl, cycloakyl, aryl aralkyl, trifluoromethyl, chlorophenyl, -SO2R (where R is alkyl, vinyl, benzyl, or phemyl), -SO2NR1R2 (where R1 and R2 are alkyl, cyclohexyl, or phenyl), sulphonic acid piperidide, esterified sulphonic acid, esterified hydroxyl, or cyano groups or halogen atoms.ALSO:Animal and vegetable fats and fatty oils are stabilized against oxidative deterioration by the addition of 0.001-1% by weight of compounds of the formula <FORM:0871196/VI/1> wherein Ar is an aryl or substituted aryl radicle and R is hydrogen or an alkyl radicle.  The radicle Ar in the formul may be phenyl, naphthyl or acenaphthenyl, and may carry substituents such as alkyl, cycloalkyl, aryl, aralkyl, trifluoromethyl, chlorophenyl, -SO2R (where R is alkyl, vinyl, benzyl or phenyl), -SO2NR1R2 (where R1 and R2 are alkyl, cyclohexyl or phenyl), sulphonic acid piperidide, esterified sulphonic acid, etherified hydroxyl, or cyano groups or halogen atoms.