Patent GB-1504573-A (GB)
Title: Phenol esters and phenol amides
IPC: C07F7/18
Filed: 1975-03-26
Abstract: 1504573 Phenol esters and phenol amides CIBA-GEIGY AG 26 March 1975 [27 March 1974] 12616/75 Headings C2C C2P and C2B [Also in Division C3] The invention comprises compounds having the general formula wherein R 1  and R 2 , which are the same or different, are alkyl, cycloalkyl or aralkyl; R 3  is hydrogen or R 3  together with R 1  is tetramethylene; R 4  denotes hydrogen or alkyl or together with R 2  denotes tetramethylene; R 5  is hydrogen, alkyl, aralkyl, acyloxyalkyl, oxaalkyl or phenyl; R 6  is hydrogen, alkyl, phenyl or the group or together with R 5  denotes alkylene; R 7  is hydrogen, alkyl, phenyl, benzyl or alkylphenyl or together with R 5  or R 6  denotes alkylene, or together with R 5  and R 6  denotes alkanetriyl, R 5 , R 6  and R 7  together containing at least one carbon atom; Y is -O- or -NH-; p is 1, 2, 3 or 4; and A is hydrogen or a group which is derived from an organic or inorganic oxy-acid A(OH)p. In preferred compounds of Formula I, p and A have the following meanings: (a) p is 1 to 4 and A is a radical of the formula wherein, if p is equal to 1, R 8  denotes an aliphatic radical, a cycloaliphatic radical, an araliphatic radical, an aryl radical, an aliphatic amido radical, a heterocyclic radical, an unsubstituted or substituted amino group, an alkoxy group, a cycloalkoxy group, an aralkoxy group, an aryloxy group or a substituted mercapto group, or p is 2 and A is a group of the Formula III wherein n denotes 0 or 1 and R 9  denotes a direct bond or a divalent aliphatic radical, cycloaliphatic radical, aromatic radical, heterocyclic radical, aliphatic diamido radical, aliphatic diamino radical, aromatic diamino radical, aliphatic dioxy radical, cycloaliphatic dioxy radical aromatic dioxy radical or aralkylenedioxy radical, or p is 3 and A denotes a group of the Formula IV wherein R 10  is a trivalent aliphatic radical, cycloaliphatic radical, aromatic radical, aliphatic trioxy radical, heterocyclic radical or a group of the Formula V wherein q denotes 1 or 2, or p is 4 and A denotes a group of the formula wherein R 11  is a tetravalent aliphatic or aromatic radical, (b) p is 1 or 2 and A is a radical of the formula wherein p+n is equal to 2 and R 12  denotes an aliphatic radical, cycloaliphatic radical, araliphatic radical or aryl radical, an unsubstituted or substituted amino group, a heterocyclic radical, an alkoxy group, a cycloalkoxy group, an aralkoxy group, an aryloxy group or a substituted mercapto group, (c) p is 3-n-n<SP>1</SP> and A is a radical of the Formula VIII wherein n and n<SP>1</SP> independently of one another denote 0 or 1 and R 13  and R 14  independently of one another denote an alkoxy group, a cycloalkoxy group, an aralkoxy group, an aryloxy group, a substituted mercapto group, a substituted amino group or a radical of a heterocyclic group, (d) p is 1 and A is a radical of the Formula IX (e) p is 3-n<SP>1</SP>-n<SP>11</SP> and A is a radical of the Formula X wherein n, n<SP>1</SP> and n<SP>11</SP> independently of one another denote 0 or 1, X denotes oxygen or sulphur, but only one phosphorus-sulphur bond may be contained in Formula X, and R 15  and R 16  independently of one another denote hydrogen or an aliphatic radical, a cycloaliphatic radical, an araliphatic radical or an aromatic radical, or R 15  and R 16  conjointly denote a divalent aliphatic or aromatic radical, (f) p is 2-n<SP>1</SP> and A is a radical of the Formula XI (XI) wherein n and n<SP>1</SP> independently of one another denote 0 or 1 and R 17  denotes an aliphatic radical, a cycloaliphatic radical, an araliphatic radical or an aromatic radical, and R 18  denotes a hydroxyl group, an alkoxy group, an aryloxy group, an aliphatic radical, a cycloaliphatic radical, an araliphatic radical or an aromatic radical, (g) p is 2- m  and A is a radical of the Formula XII (XII)   wherein m and n are each 0 or 1 and R 19  is an aromatic radical or a radical of Formula where R 20  is a divalent aromatic radical linked to the sulphur atom of (XII), or (h) p is 3 and A is a radical of formula The compounds of Formula (I) may be prepared by reacting an alcohol or amine of formula with an oxy-acid of formula The compounds of the invention may be used to stabilize organic materials against thermooxidative degradation. Reference has been directed by the Comptroller to Specification 1,458,063.