US006872832B2  Galbo et al.  (10)  Patent No.:  US 6,872,832 B2  *Mar.29,2005  (45)  Date of Patent:  (12)  United States Patent  ~4)  HYDROXY SUBSTITUTED N-ALKOXY  HINDERED AMINES AND COMPOSITIONS  STABILIZED THEREWITH  (75)  Inventors:  James Peter Galbo,  Wingdale, NY  (US);  Robert E. Detlefsen,  Putnam  Valley, 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 302 days.  This patent is subject to a terminal dis› claimer.  (21)  Appl. No.:  10/209,352  (22)  Filed:  Jul. 31, 2002  ( 63)  Continuation of application No. 09/969,737, filed on Oct. 3,  2001, now Pat. No. 6,586,507, which is a 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  ....................  C07D 211/94;  C07D 403/122  (52)  U.S. Cl.  ........................................  546/207;  546/242  (58)  Field of Search  ............................ 546/14, 19, 180,  546/188, 189, 190, 191, 198, 208, 209,  212,228,242,244,245,207  (65)  Prior Publication Data  Related U.S. Application Data  US 2003/0120077 Al Jun. 26, 2003  (56)  References Cited  U.S. PATENT DOCUMENTS  4,972,009 A  11/1990 Suhadolnik et al. .......... 524/99  5,004,770 A  4/1991 Cortolano et al. ............ 524/99  5,096,950 A  3/1992 Galbo et al. .................. 524/99  5,204,473 A  4/1993 Winter et al. ............... 546/188  5,627,248 A  5/1997 Koster et al. ............... 526/217  5,844,025 A  12/1998 Cunkle et al. ................ 524/99  6,114,420 A  9/2000 Zedda et al. ................ 524/100  6,271,377  Bl  *  8/2001 Galbo et al. .................. 546/14  6,573,346  Bl  6/2003 Melchiors et al. .......... 526/217  EP  EP  EP  EP  EP  WO  0135280  0427672  1083169  1083186  1188742  00/78709  3/1985  5/1991  3/2001  3/2001  3/2002  5/2000  FOREIGN PATENT DOCUMENTS  OTHER PUBLICATIONS  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.  Chemical Abstract No. 134:223147 for EP 1083169 (2001).  *  cited by examiner  Primary Examiner-Richard  L. Raymond  (74)  Attorney, Agent, or Firm-Tyler  A. Stevenson  Hindered amines 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 moi› eties.  (57)  ABSTRACT  6  Claims, No Drawings 