SUBSTITUTED PIPERAZINES AND POLYMERIC COMPOSITIONS STABILIZED THEREBY

摘要

1418783 Substituted piperazines CIBAGEIGY AG 29 March 1973 [29 March 1972] 15102/73 Heading C2C [Also in Division C3] The invention comprises compounds of Formula I wherein R1 or R2 are independently C 1 -C 12 alkyl or R1 and R2 together with the carbon atom to which they are attached form a C 5 -C 12 mono-carbocyclic ring system; n = 1 or 2; when n is 1 R3 is H, C 1 -C 20 alkyl, benzyl or a group of Formula Ia when R4 = H or CH 3 , R5 is C 1 -C 20 alkyl and m = 0 or 1; when n = 2 R3 is C 1 -C 20 alkylene. The compounds of Formula I in which R3 is other than H or the ester group of Formula Ia may be prepared by reacting a compound of Formula II or an alkali metal or alkaline earth metal salt thereof with an organic mono or dihalo compound of formula where R3 is C 1 -C 20 alkyl or alkylene or benzyl, X is halogen, preferably Cl, and n is 1 or 2, followed by reduction with LiAlH 4 . Compounds of Formula I in which R3 is H may be obtained by reduction of a compound of Formula II with LiAlH 4 . The compounds of Formula I in which R3 is a group of formulµ may be obtained by reacting a compound of formula III with an acylate of formula or a haloester of formula where X is a halogen, e.g. Cl or Br, respectively. 1 - Aminocyclohexanecarbonitrile and 1 - animoisobutyronitrile are prepared by reaction of anhydrous NH 3 with cyclohexanone and acetone cyanohydrin respectively. Bis - (1 - cyanocyclohexyl)amine and bis- (1 - cyanoisopropyl)amine are prepared from the aminonitriles above by heating under vacuum. 7,15 - Diazadispiro[5,1,5,3]hexadecane - 14,16- dione and 2,2,6,6 - tetramethyl - 3,5 - diketopiperazine are prepared from the above amines by reaction with 96% H 2 SO 4 and are reduced with LiAlH 4 to obtain 7,15-diazadispiro- [5,1,5,3]hexadecane and 2,2,6,6 - tetramethylpiperazine respectively. The compounds of Formula I are useful in stabilizers for many polymeric materials against U.V. deterioration.