US 7,485,723 B2
Process for making trisaryl triazine UV absorbers using Lewis acids and reaction promoters
Ram B. Gupta, Stamford, Conn. (US); Dennis J Jakiela, Orange, Conn. (US); Sampath Venimadhavan, Stamford, Conn. (US); Russell C Cappadona, Norwalk, Conn. (US); and Venkatrao K. Pai, Stamford, Conn. (US)
Assigned to Cytec Technology Corp., Wilmington, Del. (US)
Filed on Sep. 14, 2006, as Appl. No. 11/531,932.
Application 09/779597 is a division of application No. 09/442000, filed on Nov. 17, 1999, granted, now 6,486,316.
Application 11/531932 is a continuation of application No. 11/089289, filed on Mar. 24, 2005, abandoned.
Application 11/089289 is a continuation of application No. 10/835731, filed on Apr. 30, 2004, granted, now 6,900,314.
Application 10/835731 is a continuation of application No. 09/779597, filed on Feb. 09, 2001, granted, now 6,730,785.
Claims priority of provisional application 60/108786, filed on Nov. 17, 1998.
Prior Publication US 2007/0015920 A1, Jan. 18, 2007
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 251/24 (2006.01)
U.S. Cl. 544—216  [544/217] 21 Claims
 
1. A process for synthesizing a trisaryl triazine compound comprising reacting a cyanuric halide of Formula V:

OG Complex Work Unit Drawing
where each X is independently a halide such as fluorine, chlorine, bromine or iodine, with a compound of Formula II:

OG Complex Work Unit Drawing
wherein R6, R7, R8, R9, and R10 are the same or different and each is hydrogen, halogen, alkyl of 1 to 24 carbon atoms, haloalkyl of 1 to 24 carbon atoms, aryl of 6 to 24 carbon atoms, alkenyl of 2 to 24 carbon atoms, acyl of 1 to 24 carbon atoms, aralkyl of 7 to 24 carbon atoms, aracyl of 6 to 24 carbon atoms, OR, NRR′, CONRR′, OCOR, CN, SR, SO2R, SO3H, SO3M, wherein M is an alkali metal, R and R1 are the same or different and each is hydrogen, alkyl of 1 to 24 carbon atoms, haloalkyl of 1 to 24 carbon atoms, aryl of 6 to 24 carbon atoms, alkenyl of 2 to 24 carbon atoms, acyl of 1 to 24 carbon atoms, cycloalkyl of 1 to 24 carbon atoms, cycloacyl of 5 to 24 carbon atoms, aralkyl of 7 to 24 carbon atoms, or aracyl of 6 to 24 carbons atoms, and optionally with either of R6 and R7, R7 and R8, R8 and R9, or R9 and R10, taken together being a part of a saturated or unsaturated fused carbocyclic ring optionally containing O, N, or S atoms in the ring, in the presence of at least one solvent and a reaction facilitator comprising at least one Lewis acid and at least one reaction promoter, for a sufficient time, at a suitable temperature and pressure to form the trisaryl triazine compound, with the proviso that the reaction promoter is different than the compound of Formula II.