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# (12) United States Patent 

# Galbo et al. 

# ~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. 

(21) Appl. No.: 10/209,352 

(22) Filed: Jul. 31, 2002 

## (65) Prior Publication Data 

US 2003/0120077 Al Jun. 26, 2003 

( 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 

## (56) References Cited 

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This patent is subject to a terminal dis› claimer. 

## Related U.S. Application Data 

## U.S. PATENT DOCUMENTS 

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# (10) Patent No.: US 6,872,832 B2 

# *Mar.29,2005 (45) Date of Patent: 

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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 

## (57) ABSTRACT 

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. 

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US006872832B2 

## FOREIGN PATENT DOCUMENTS 

## OTHER PUBLICATIONS 

## 6 Claims, No Drawings 

