Derivatives of 2-oxazoline useful as antioxidants

C - Chemistry – Metallurgy – 07 – D

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C07D 263/14 (2006.01) C08K 5/35 (2006.01) C09K 15/30 (2006.01)

Patent

CA 1133908

ABSTRACT OF THE DISCLOSURE Compounds cont?ning pendant 3,5-di-alkyl-4- hydroxyphenyl groups are useful as antioxidants for protecting organic materials (for example, plastics, synthetic and natural rubbers and petroleum products) that are normally subject to oxidative degradation. These compounds have the formula Image I wherein B is hydrogen, C1 to C4 alkyl, -CH2OH or -CH2O?-Y; Y is hydrogen, C1 to C30 alkyl, C? to C8 cycloalkyl, C6 to C10 aryl, substituted aryl or A, wherein A is Image , wherein R and R1 may be the same or different and are C1 to C12 alkyl or C8 to C10 aralkyl; D is hydrogen, C1 to C4 alkyl, -CH2OH or CH2O?-Z; Z is hydrogen, C1 to C30 alkyl, C4 to C8 cycloalkyl, C6 to C10 aryl, C6 to C10 aryl substituted with C1 to C12 alkyl, nitro, amino, hydroxyl or halogen, or Z is A, wherein A is as defined above, or Z is a divalent group connecting two oxazoline moieties, an oxazoline moiety being a group of the formula Image ; n is an integer equal to 0 or 1; with the proviso that when n equals 0, X is hydrogen, C1 to C30 alkyl, C4 to C8 cycloalkyl, C6 to C10 aryl, C6 to C10 aryl substituted with C1 to C12 alkyl, nitro, amino, hydroxyl or halogen, or X is A, wherein A is as defined above, or X is Image , wherein Q is C4 to C8 alkylene, thiodiethylene or phenylene, with the proviso that Q and Z cannot be divalent at the same time and that either X must be the radical A, or if X is not the radical A, then B must be the radical E, wherein Z is -CH2O-?-A, and when n equals 1, W is -CH2OH or E, wherein E is as defined above, V is C1 to C4 alkyl, -CH2OH or E, wherein E is as defined above, or V and W taken together form a ? CH2 group X is C1 to C30 alkyl, C4 to C8 cycloalkyl, C6 to C10 aryl, aryl substituted with C1 to C12 alkyl, nitro, amino, hydroxyl or halogen, or X is Image or Image II wherein R and R1 are as defined above, Q is C2 to C6 alkylene, thiodimethylene or phenylene, with the proviso that Q and Z cannot be divalent at the same time and that either X must be a radical of the formula II or B or W must be E, wherein E is as defined above.

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