Patent DE-19907945-A1 (DE)
Title: Preparation of sterically hindered amine ethers used as stabilizers against light, oxygen and/or heat or yellowing
Inventor: ZEDDA ALESSANDRO
IPC: C08K5/3492
Filed: 1999-02-24
Abstract: The preparation comprises the oxidation of a specified 1-allyl-substituted sterically hindered amine. A process for preparing a compound of formula (I) comprises oxidizing a compound of formula (II); R1-R4 = 1-8C alkyl or 1-5C hydroxyalkyl; or R1 and R2, together with the carbon atom they are attached to, are 5-12C cycloalkyl; or R3 and R4, together with the carbon atom they are attached to, are 5-12C cycloalkyl; R5-R9 = H, 1-8C alkyl, 2-8C alkenyl, 5-12C aryl, 1-4C haloalkyl, an electron withdrawing group, or 6-12C aryl which is substituted by a residue from 1-4C alkyl, 1-4C alkoxy, halogen; and R7 and R8 together may also form a chemical bond; and R = an organic linking group containing 2-500C atoms and forming, together with the carbon atoms it is directly connected to and the nitrogen atom, a substituted, 5-, 6 or 7-membered cyclic ring structure. Independent claims are also included for: (A) a process for preparing a compound of formula (V), in which a compound of formula (II) is oxidized and the resulting intermediate of formula (I) is subjected to hydrogenation and/or halogenation; (B) a composition which comprises: (a) an organic polymer which is sensitive to oxidative, thermal and/or actinic degradation; and (b) at least one compound of formula (IlIa), (IVa) or (Va); (C) a compound of formula (Ia); and (D) the compounds of formula (IlIa), (IVa) or (Va). R, R1-R6 and R9 = as above; R7 and R8 = H, 1-8C alkyl, 3-8C alkenyl, 5-12C aryl, 1-4C haloalkyl, halogen, an electron withdrawing group, or 6-12C aryl which is substituted by 1-4C alkyl, 1-4C alkoxy or halogen; and R20 and R21 = H or halogen. R' and R = an organic linking group of formula -CH2-E1-E2- (VI); E2 = -CO- or -(CH2)p- (p = 0, 1 or 2); E1 = a carbon atom carrying the two residues R24 and R25 or is \>N-R25 or oxygen; R24 and R25 = hydrogen or an organic residue; R has 2-500C atoms; R1-R9 = as above; R20 and R21 = halogen; and R22 and R23 = hydrogen or together are a chemical bond. n = 1-15. R5-R9 = 1-8C alkyl, 3-8C alkenyl, 5-12C aryl, an electron withdrawing group, 6-12C aryl which is substituted by 1-4C alkyl, 1-4C alkoxy or halogen; R12 = 2-12C alkylene, 4-12C alkenylene, 5-7C cycloalkylene, 5-7C cycloalkylene-di(1-4C alkylene), 1-4C alkylene-di(5-7C cycloalkylene), phenylene-di(1-4C alkylene), 4-12C alkylene interrupted by 1,4-piperazinediyl, -O- or \>N-X1, or R12 is a group of the formula (Ib') or (Ic'); X1 = 1-12C acyl, (1-12C alkoxy)carbonyl or has one of the definitions of R14 below except hydrogen; m = 2 or 3; X2 = 1-8C alkyl, 5-12C cycloalkyl which is optionally substituted by 1, 2 or 3 1-4C alkyl; phenyl which is optionally substituted by 1, 2 or 3 1-4C alkyl or  1-4C alkoxy; 7-9C phenylalkyl which is optionally substituted on the phenyl by 1, 2 or 3 1-4C alkyl; and X3 = 2-12C alkylene; A = -OR13, -N(R14)(R15) or a group of formula (Id'); R13-R15 = hydrogen, 1-18C alkyl, 5-12C cycloalkyl which is optionally substituted by 1, 2 or 3 1-4C alkyl; 3-18C alkenyl, phenyl optionally substituted by 1, 2 or 3 1-4C alkyl or 1-4C alkoxy; 7-9C phenylalkyl which is optionally substituted on the phenyl by 1, 2 or 3 1-4C alkyl; tetrahydrofurfuryl or 2-4C alkyl which is substituted in the 2, 3 or 4 position by -OH, 1-8C alkoxy, di(1-4C alkyl)amino or a group of formula (le'); Y = -O-, -CH2-, -CH2CH2- or \>N-CH3; or -N(R14)(R15) = optionally a group of the formula (le'); X = -O- or \>NR16; R16 = hydrogen, 1-8C alkyl, 3-18C alkenyl, 5-12C cycloalkyl which is optionally substituted by 1, 2 or 3 1-4C alkyl; 7-9C phenylalkyl which is optionally substituted on the phenyl by 1, 2 or 3 1-4C alkyl; tetrahydrofurfuryl; a group of formula (If') or 2-4C alkyl which is substituted in the 2, 3 or 4 position by -OH, 1-8C alkoxy, di(1-4C alkyl)amino or a group of formula (le'); R11 = as R16; and B = as A.