Patent GB-1078772-A (GB)
Title: Anti-oxidants
Inventor: UNION CARBIDE CO
IPC: C09K15/08
Filed: 1964-07-01
Abstract: Antioxidant compositions for liquid hydrocarbon fuels, lubricating oils, refined industrial oils, waxes, soaps, greases and fats and oils of animal or vegetable origin comprise a phosphite of a phenol of formula <FORM:1078772/C4-C5/1> wherein R and R1 are the same or different and are hydrogen or monovalent hydrocarbon radicals containing from 3 to 9 carbon atoms and R2 is a monovalent hydrocarbon radical containing from 4 to 20 carbon atoms inclusive and a phenol having the formula <FORM:1078772/C4-C5/2> wherein R4 is as defined for R2, R5 is hydrogen or a tertiary alkyl radical containing from 3 to 9 carbon atoms, the phenol being present in amount from 10 to 90% of the phenol and phosphite. Specified phosphites are (1) di-(2-t.-butyl - 4 - dodecyl - phenyl phosphite, (2) di-(p - dodecylphenyl) phosphite; (3) tri-(p-dodecyl phenyl) phosphite and (4) di-(2-t.-butyl - 4 - nonylphenyl) phosphite while the phenol may be (5) 2-t.-butyl-4-dodecylphenol, (6) 2,6 - di - t.- - butyl - 4 - dodecyl phenol, (7) 2 - t. - butyl - 4 - nonyl phenol or mixtures thereof.  Specified antioxidants are mixtures of (A) (1), (5) and (6), (B) (2), (5) and (6), (C) (3), (5) and (6), (D) (1) and (4), and (E) (1) and (5).ALSO:Antioxidant compositions for natural rubbers, synthetic rubbers, e.g. butadiene, isoprene, and 2-3-dimethyl butadiene homopolymers and their copolymers with styrene, other aryl olefins, acrylic and substituted acrylic acids, esters nitriles and amides, vinyl methyl ketone, vinyl methyl ether, vinylidene chloride, N-vinyl carbazole, and N-vinyl pyrrolidone, ethylenepropylene and ethylene-propylene-diene copolymers, and thermoplastic polymers, e.g. polyethylene and polypropylene comprise a phosphite of a phenol of formula <FORM:1078772/C3/1> wherein R and R1 are the same or different and are hydrogen or monovalent hydrocarbon radicals containing from 3 to 9 carbon atoms and R2 is a monovalent hydrocarbon radical containing from 4 to 20 carbon atoms inclusive, and a phenol having the formula <FORM:1078772/C3/2> wherein R4 is as defined for R2, R5 is hydrogen or a tertiary alkyl radical containing from 3 to 9 carbon atoms, the phenol being present in amount from 10 to 90% of the phenol and phosphite. Specified phosphites are (1) di-(2-t.-butyl - 4 - dodecyl - phenyl) phosphite; (2) di(p - dodecylphenyl) - phosphite; (3) tri - (p - dodecylphenyl phosphite) and (4) di(2-t.-butyl-4-nonylphenyl) phosphite while the phenol may be (5) 2-t.-butyl-4-dodecyl phenol; (6) 2,6-di-t.-butyl - 4 - dodecyl phenol; (7) 2 - t. - butyl - 4 - nonyl phenol or mixtures thereof. Specified antioxidants are mixtures of (A) (1), (5) and (6), (B) (2), (5) and (6), (C) (3), (5) and (6), (D) (1), and (4), and (E) (1) and (5).ALSO:A butylated dodecyl phenol made up predominantly of a phenol of formula <FORM:1078772/C2/1> is prepared by heating at 95 DEG  C. a mixture of dodecyl phenol, toluene and a boron trifluoridephosphoric acid complex and bubbling through isobutylene. Toluene is then added, the mixture cooled to 75 DEG  C., washed, the aqueous phase siphoned off and the mixture distilled.  A phosphite derivative of the above butylated dodecyl phenol made up predominantly of a phosphite of formula <FORM:1078772/C2/2> is prepared by refluxing the butylated dodecyl phenol and a solution of toluene and phosphorus trichloride at 70 DEG  C.ALSO:An antioxidant comprises a phosphite of a phenol of formula:  <FORM:1078772/B1-B2/1> wherein R and R1 are the same or different and are hydrogen or monovalent hydrocarbon radicals containing from 3 to 9 carbon atoms and R2 is a monovalent hydrocarbon radical containing from 4 to 20 carbon atoms inclusive, and a phenol having the formula: <FORM:1078772/B1-B2/2> wherein R4 is as defined for R2, R5 is hydrogen or a tertiary alkyl radical containing from 3 to 9 carbon atoms, the phenol being present in amount from 10 to 90 per cent of the phenol and phosphate.  Specified phosphites are (1) di(2-t-butyl-4-dodecyl-phenyl) phospite, (2) di(p-dodecylphenyl)-phosphite, (3) tri (p-dodecylphenyl) phosphite, or (4) di(2-t-butyl-4-nonylphenyl) phosphite while the phenol may be (5) 2-t-butyl-4-dodecylphenol, (6) 2,6-di-t-butyl-4-dodecylphenol, (7) 2-t-butyl-4-nonylphenol or mixtures thereof.  Specified anti-oxidants are mixtures of (A) (1), (5) and (6), (B) (2), (5) and (6), (C) (3), (5) and (6), (D) (1) and (4) and (E) (1) and (5).  The substances to which the anti-oxidant mixture may be added are rubbers, thermo - plastic resins, liquid hydrocarbon fuels, lubricating oils and functional fluids in general especially silicone fluids, refined industrial oils, waxes, soaps, greases and fats and oils of animal or vegetable origin.