Process for making triazine UV absorbers using Lewis acids and reaction promoters

A process for synthesizing a triazine compound of the Formula I:

• which comprises the following steps:
• (i) reacting a cyanuric halide of the Formula V:
• where each X is independently a fluorine, chlorine, bromine, or iodine, with at least one compound of Formula II:
• 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 R′ 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, with the reaction being conducted in the presence of a first reaction facilitator comprising sufficient amounts of a first Lewis acid and a first reaction promoter, wherein the reaction promoter is present in an amount of about 0.1 to about 5 mol equivalents to the compound of Formula V, optionally in the presence of at least one solvent, for a sufficient time at a suitable temperature and pressure to produce a triazine compound of Formula III:
• wherein X is a halogen and Ar1 and Ar2 are the same or different and each is a radical of a compound of Formula II;
• and
• (ii) reacting a compound of Formula III with a compound of Formula IV:
• wherein
• R1 and R2 each independently is alkyl of 1 to 24 carbon atoms, haloalkyl of 1 to 24 carbon atoms, alkenyl of 2 to 24 carbon atoms, acyl of 1 to 24 carbon atoms, aryl of 6 to 24 carbon atoms, cycloalkyl of 5 to 25 carbon atoms, cycloacyl of 5 to 24 carbon atoms, aralkyl of 7 to 24 carbon atoms, aracyl of 6 to 24 carbons atoms;
• R3, R4,and R5 are the same or different and each is hydrogen, halogen, alkyl of 1 to 24 carbon atoms, haloalkyl of 1 to 24 carbon atoms, alkenyl of 2 to 24 carbon atoms, acyl of 1 to 24 carbon atoms, aryl of 6 to 24 carbon atoms, cycloalkyl of 5 to 25 carbon atoms, cycloacyl of 5 to 24 carbon atoms, aralkyl of 7 to 24 carbon atoms, aracyl of 6 to 24 carbons atoms, OR, NRR′, CONRR′, OCOR, CN, SR, SO2R, SO3H, SO3M, wherein M is an alkali metal, R and R′ 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, optionally with either of R3 and R4, or R4 and R5, taken together being a part of a saturated or unsaturated fused carbocyclic ring optionally containing O, N, or S atoms in the ring;
• and
• Y is a direct bond, O, NR″, or S, wherein R″ 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, for a sufficient time, at a suitable temperature and pressure in the presence of a second Lewis acid, a second reaction promoter, or a second reaction facilitator to form the compound of Formula I,
• wherein the first and second reaction promoters are compounds different than the solvent, or the compound of Formula II, and wherein the compound of Formula II is not the same as the compound of Formula IV.