Benzoxazole stabilizer compounds and polymeric materials stabilized therewith

• US 4,579,893 A
• Filed: 01/06/1984
• Issued: 04/01/1986
• Est. Priority Date: 01/06/1984
• Status: Expired due to Fees

• Current Assignee: Eastman Chemical Company
• Original Assignee: Eastman Kodak Company
• Inventors: Wang, Richard H. S., Bellas, Michael, Blount, William W. Jr.
• Primary Examiner(s): Lee, Lester L.
• Application Number:
  US06/568,569
• Time in Patent Office: 816 Days
• Field of Search: 524/87, 524/90, 524/601, 524/604, 524/605, 524/590, 524/556, 524/560, 548/217
• US Class Current: 524/87
• CPC Class Codes: C07D 263/57 Aryl or substituted aryl radicals
• CPC Class Codes: C08K 5/35 having also oxygen in the ring

Abstract

Disclosed are compounds having the formula ##STR1## wherein X is the residue of a benzoxazole radical;

Y is carboxyl, alkoxycarbonyl, alkanoyl, cyano, carbamoyl, N-alkylcarbamoyl or N,N-dialkylcarbamoyl; and

A is phenyl, naphthyl or phenyl or napthyl substituted with one or more substituents selected from hydroxy, halogen, alkyl, alkoxy, cycloalkyl, aryl, aryloxy or Y. Also disclosed are polymeric materials stabilized against degradation by ultraviolet light by the incorporation therein of one or more of the above-defined compounds.

Claims

1. A compound having the formula ##STR9## wherein R¹ is hydrogen, alkyl, alkoxy or halogen;

R² is an R¹ substituent, carboxyl or alkoxycarbonyl;

Y is carboxyl, alkoxycarbonyl, alkanoyl, cyano, carbamoyl, N-alkylcarbamoyl or N,N-dialkylcarbamoyl; and

A is phenyl or phenyl substituted with one or more substituents selected from hydroxy, halogen, alkyl, alkoxy, cycloalkyl, aryl, aryloxy or Y.

2. A compound having the formula ##STR10## wherein R¹ is hydrogen, alkyl, alkoxy or halogen;

R² is an R¹ substituent, carboxyl or alkoxycarbonyl; and

R³ and R⁴ are independently selected from hydrogen, alkyl, alkoxy, hydroxy, halogen, cycloalkyl, aryl or aryloxy.

3. A compound having the formula ##STR11## wherein R² is hydrogen, alkyl, alkoxy, chlorine, carboxyl or alkoxycarbonyl;

Y is alkoxycarbonyl or cyano; and

R³ is ortho or para hydroxy or alkoxy.

4. A compound having the formula ##STR12##

5. A compound having the formula ##STR13##

6. A compound having the formula ##STR14##

7. A compound having the formula ##STR15##

8. A stabilized composition comprising an organic material normally degraded by exposure to ultraviolet light containing a stabilizing amount of a compound having the formula ##STR16## wherein R¹ is hydrogen, alkyl, alkoxy or halogen;

R² is an R¹ substituent, carboxyl or alkoxycarbonyl;

Y is carboxyl, alkoxycarbonyl, alkanoyl, cyano, carbamoyl, N-alkylcarbamoyl or N,N-dialkylcarbamoyl; and

A is phenyl or phenyl substituted with one or more substituents selected from hydroxy, halogen, alkyl, alkoxy, cycloalkyl, aryl, aryloxy or Y.

9. A stabilized composition according to claim 8 wherein the organic material comprises a polymer containing ester groups.

10. A stabilized polymeric composition comprising a polyester containing recurring phthalate moieties and a stabilizing amount of a compound having the formula ##STR17## wherein R² is hydrogen, alkyl, alkoxy, chlorine, carboxyl or alkoxycarbonyl;

Y is alkoxycarbonyl or cyano; and

R³ is ortho or para hydroxy or alkoxy.