US006391949B2  (12)  United States Patent  Galbo et al.  (10)  Patent No.:  US 6,391,949 B2  May 21, 2002  (45)  Date of Patent:  (54)  HYDROXY-SUBSTITUTED N-ALKOXY  HINDERED AMINES AND COMPOSITIONS  STABILIZED THEREWITH  (75)  Inventors:  James P. 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;  Peter Solera,  Suffern, both of  NY  (US)  (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.:  09/790,828  (22)  Filed:  Feb.22,2001  (62)  Division of application No. 09/257,711, filed on Feb. 25,  1999, now Pat. No. 6,271,377.  (51)  Int. Cl.7  ..................................................  C08K 5/34  (52)  U.S. Cl.  .........................  524/102;  523/122; 524/90;  524/91; 524/96; 524/100; 524/101; 524/126;  524/128; 524/132; 524/144; 524/153; 524/291;  524/359; 524/371; 524/399; 524/404; 524/425;  524/432; 524/445; 524/449; 524/492; 524/494  (58)  Field of Search  ............................ 523/122; 524/90,  524/91, 96, 100, 101, 102, 126, 128, 132,  144,153,291,359,371,399,404,425,  432,445,449,492,494  Related U.S. Application Data  (56)  References Cited  U.S. PATENT DOCUMENTS  FOREIGN 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  OTHER PUBLICATIONS  36 Claims, No Drawings  (57)  ABSTRACT  Nigam et al,  J.  Chem. Soc., Trans. Faraday Soc., 1, 1976, 72,  pp. 2324-2340.  Asmas et al., Int.  J.  Radiat. Biol., 1976, 29, pp. 211-219.  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.  Primary Examiner----Kriellion  A. Sanders  (74)  Attorney, Agent, or Firm-Tyler  A. Stevenson; Luther  AR. Hall  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. 