US006586507B2  (12)  United States Patent  Galbo et al.  (10)  Patent No.:  US 6,586,507 B2  Jul. 1, 2003  (45)  Date of Patent:  (54)  HYDROXY-SUBSTITUTED N-ALKOXY  HINDERED AMINES AND COMPOSITIONS  STABILIZED THEREWITH  (75)  Inventors:  James Peter Galbo,  Wingdale,  NY  (US);  Gerald A. Capocci,  Greenwich,  CT (US);  Nancy N. Cliff,  Ringwood,  NJ (US);  Robert E. Detlefsen,  Putnam  Valley,  NY  (US);  Michael P. DiFazio,  Mobile, AL (US);  Ramanathan  Ravichandran,  Nanuet,  NY  (US);  Peter Solera,  Suffern,  NY  (US);  Christophe Bulliard,  Basel (CH)  (73)  Assignee:  Ciba Specialty Chemicals  Corporation,  Tarrytown,  NY  (US)  ( *)  Notice:  Subject to any disclaimer, the term of this  patent is extended or adjusted under 35  U.S.C. 154(b) by  O  days.  (21)  Appl. No.:  09/969,737  (22)  Filed:  Oct. 3, 2001  (65)  Prior Publication Data  US 2002/0058735 Al May 16, 2002  Related U.S. Application Data  (60)  Division of application No. 09/505,529, filed on Feb. 17,  2000, now Pat. No. 6,392,041, which is a continuation-in› part of application No. 09/257,711, filed on Feb. 25, 1999,  now Pat. No. 6,271,377.  (51)  Int. Cl.7  .....................  C0SK 5/3435;  C08K 5/3492  (52)  U.S. Cl.  ...........................  524/102;  524/91; 524/94;  524/99; 524/100; 524/101; 524/125; 524/127;  524/149; 524/189; 524/290; 524/359; 524/371;  524/394; 524/399; 524/409; 524/432; 524/425;  524/442; 524/445; 524/449; 524/451; 524/494  (58)  Field of Search  .............................. 524/91, 94, 99,  524/100, 101,102,125,127,149,189,  290, 359, 371, 399, 425, 445, 449, 451,  432, 494, 442, 409  (56)  References Cited  U.S. PATENT DOCUMENTS  4,972,009 A  5,004,770 A  5,096,950 A  5,204,473 A  5,627,248 A  5,844,025 A  6,114,420 A  11/1990 Suhadolnik et al. .......... 524/99  4/1991 Cortolano et al. ............ 524/99  3/1992 Galbo et al. .................. 524/99  4/1993 Winter et al. ............... 546/188  5/1997 Koster et al. ............... 526/217  12/1998 Cunkle et al. ................ 524/99  9/2000 Zedda et al. ................ 524/100  EP  EP  WO  0135280  0427672  00/78709  3/1985  5/1991  5/2000  FOREIGN PATENT DOCUMENTS  OTHER PUBLICATIONS  (57)  ABSTRACT  34 Claims, No Drawings  S.  Nigam et al.,  J.  Chem. Soc., Trans. Faraday Soc. 1,  (1976), vol. 72, pp. 2324--2340.  K.-D. Asmus et al., Int.  J.  Radiat. Biol., (1976), vol. 29, No.  3, pp. 211-219.  Chemical Abstr. 125:329586 for  J.  Am. Chem. Soc. (1996),  118(46), pp. 11467-11471.  D. Gravert et al.,  J.  Am. Chem. Soc. (1998), vol. 120, pp.  9481-9495.  C. Hawker et al., JACS, vol. 118, No. 46, (1996), pp.  11467-11471.  Hindered ammes substituted on the N-atom with an  -O-E-OH  moiety are particularly effective in stabilizing  polyolefin and automotive coating compositions against the  deleterious effects of oxidative, thermal and actinic radiation  where the presence of the  OH  group on the compounds adds  important properties not attainable by the use of normal  -O-E moieties.  Primary Examiner----Kriellion  A. Sanders  (74)  Attorney, Agent, or Firm-Tyler  A. Stevenson; Luther  AR. Hall 