US2003065178A1PendingUtilityA1
Process for making 2-hydroxy-4-alkoxyphenyl or 2,4-dihydroxyphenyl substituted 1,3,5-triazine UV absorbers
Priority: Sep 4, 1998Filed: Oct 2, 2002Published: Apr 3, 2003
Est. expirySep 4, 2018(expired)· nominal 20-yr term from priority
C07D 251/20C07D 251/22C07D 251/24
45
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Claims
Abstract
The invention provides new processes for preparing compositions containing at least one triazine compound, including new compounds for use in these processes to form the compositions and the new compositions that are formed.
Claims
exact text as granted — not AI-modifiedWhat is claimed is:
1 . A process for preparing a composition comprising at least one triazine compound of Formula A:
wherein Ar 1 and Ar 2 are the same or different, and each independently is a radical of a compound of Formula B:
wherein R 1 , R 2 , R 3 , R 4 and R 5 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 24 carbon atoms, cycloacyl of 5 to 24 carbon atoms, aralkyl of 7 to 24 carbon atoms, aracyl of 6 to 24 carbon atoms, OR, NRR′, CONRR′, OCOR, CN, SR, SO 2 R, SO 3 H, SO 3 M, 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, 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 24 carbon atoms, cycloacyl of 5 to 24 carbon atoms, aralkyl of 7 to 24 carbon atoms, or aracyl of 6 to 24 carbon atoms, optionally with either of R 3 and R 4 , or R 4 and R 5 , 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 SR″, wherein R″ is hydrogen, 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 24 carbon atoms, cycloacyl of 5 to 24 carbon atoms, aralkyl of 7 to 24 carbon atoms or aracyl of 6 to 24 carbon atoms; or a radical of a compound of Formula C:
wherein R 6 , R 7 , R 8 , R 9 and R 10 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, SO 2 R, SO 3 H, SO 3 M, 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 5 to 24 carbon atoms, cycloacyl of 5 to 24 carbon atoms, aralkyl of 7 to 24 carbon atoms, or aracyl of 6 to 24 carbon atoms, and optionally with either of R 6 and R 7 taken together, R 7 and R 8 taken together, R 8 and R 9 taken together, or R 9 and R 10 taken together being a part of a saturated or unsaturated fused carbocyclic ring optionally containing O, N or S atoms in the ring, which process comprises:
(i) reacting in the presence of a first catalyst, sufficient amounts of a compound of Formula D:
wherein X is a halogen,
and a compound of Formula E:
wherein R 1 , R 2 , R 3 , R 4 and R 5 are as described above, at a suitable temperature and pressure in the presence of a solvent and for a time sufficient to form a reaction mixture comprising the composition.
2 . A process for preparing a composition comprising at least one triazine compound of Formula A:
wherein Ar 1 and Ar 2 are the same or different, and each independently is a radical of a compound of Formula B:
wherein Y, R 1 , R 2 , R 3 , R 4 and R 5 are as described above, or a radical of a compound of Formula C:
wherein R 6 , R 7 , R 8 , R 9 and R 10 are as described above, which process comprises:
(i) reacting in the presence of a first catalyst, sufficient amounts of a compound of Formula D:
wherein X is a halogen,
and a compound of Formula E:
wherein R 1 , R 2 , R 3 , R 4 and R 5 are as described above, at a suitable temperature and pressure, and for a time sufficient to produce a first reaction mixture comprising at least one intermediate compound of:
wherein Ar 1 , X, R 1 , R 2 , R 3 , R 4 , and R 5 are as defined above; and
(ii) reacting the first reaction mixture and a compound of Formula F:
wherein R 6 , R 7 , R 8 , R 9 and R 10 are as defined above, in the presence of a second catalyst and at a suitable temperature and pressure, and for a time sufficient to produce a second reaction mixture comprising the composition.
3 . The process of claim 1 wherein the composition further comprises a compound of Formula G:
wherein Ar 1 , R 1 , R 2 , R 3 , R 4 , and R 5 are as defined above.
4 . The process of claim 2 wherein at least one intermediate compound is isolated from the first reaction mixture.
5 . The process of claim 1 wherein the first catalyst is a Lewis acid and X is chlorine.
6 . The process of claim 5 wherein the first catalyst is selected from the group consisting of aluminum tribromide, zinc chloride, boron trichloride, titanium tetrachloride, aluminum trichloride, and a mixture thereof.
7 . The process of claim 2 wherein the second catalyst is a Lewis acid and X is chlorine.
8 . The process of claim 7 wherein the second catalyst is selected from the group consisting of aluminum tribromide, zinc chloride, boron trichloride, titanium tetrachloride, aluminum trichloride, and a mixture thereof.
9 . The process of claim 1 wherein the amount of catalyst is from about 0.5 to about 5 equivalents based upon the amount of the compound of Formula D.
10 . The process of claim 8 wherein the combined amount of first catalyst and of second catalyst is from about 0.5 to about 5 equivalents based upon the amount of the compound of Formula D.
11 . The process of claim 10 wherein the combined amount of first catalyst and of second catalyst is from about 1 to about 4 equivalents based upon the amount of the compound of Formula D.
12 . The process of claim 1 wherein the amount of the compound of Formula B is from about 0.75 to about 4 equivalents based upon the amount of the compound of Formula D.
13 . The process of claim 2 wherein the amount of the compound of Formula B is from about 0.75 to about 4 equivalents based upon the amount of the compound of Formula D.
14 . The process of claim 13 wherein the amount of the compound of Formula B is from about 1 to about 3 equivalents based upon the amount of the compound of Formula D.
15 . The process of claim 14 wherein the amount of the compound of Formula B is from about 1 to about 3 equivalents based upon the amount of the compound of Formula D.
16 . The process of claim 1 wherein the compound of Formula B and the compound of Formula D are reacted at a temperature of between about 0° C. and about 150° C.
17 . The process of claim 2 wherein the compound of Formula B and the compound of Formula D are reacted at a temperature of between about 0° C. and about 150° C.
18 . The process of claim 17 wherein the compound of Formula B and compound of Formula D are reacted at a temperature of between about 30° C. and about 100° C.
19 . The process of claim 18 wherein the compound of Formula B and compound of Formula D are reacted at a temperature of between about 30° C. and about 100 ° C.
20 . The process of claim 2 wherein the first reaction mixture and the aromatic compound are reacted at a temperature of between about 0° C. and about 150° C.
21 . The process of claim 14 wherein the first reaction mixture and the aromatic compound are reacted at a temperature of between about 30° C. and about 100° C.
22 . The process of claim 1 wherein the reaction of the compound of Formula B and the compound of Formula D is conducted in a halogenated solvent.
23 . The process of claim 2 wherein the reaction of the compound of Formula B and the compound of Formula D is conducted in a halogenated solvent.
24 . The process of claim 22 wherein the halogenated solvent is selected from the group consisting of chlorobenzene, dichlorobenzene, 1,1,2,2-tetrachloroethane, and mixtures thereof.
25 . The process of claim 2 wherein the first reaction mixture and the aromatic compound are reacted in a halogenated solvent.
26 . The process of claim 25 wherein the halogenated solvent is selected from the group consisting of chlorobenzene, dichlorobenzene, 1,1,2,2-tetrachloroethane, and mixtures thereof.
28 . A compound of Formula I:
wherein X is a halogen; and R 1 , R 2 , R 3 , R 4 or R 5 are as described above.
28 . A process for preparing a composition comprising at least one triazine compound of Formula A:
wherein Ar 1 and Ar 2 are the same or different, and each independently is a radical of a compound of Formula B:
wherein Y, R 1 , R 2 , R 3 , R 4 and R 5 are as described above, or a radical of a compound of Formula C:
wherein R 6 , R 7 , R 8 , R 9 and R 10 are as described above, which process comprises:
reacting the triazine compound of claim 27 with a compound of Formula F:
wherein R 6 , R 7 , R 8 , R 9 and R 10 are as defined above, in the presence of a catalyst and at a suitable temperature and pressure, and for a time sufficient to produce a reaction mixture comprising the composition.
29 . A process for preparing a composition comprising at least one triazine compound of Formula A:
wherein Ar 1 and Ar 2 are the same or different, and each independently is a radical of a compound of Formula B:
wherein Y, R 1 , R 2 , R 3 , R 4 and R 5 are as described above, or a radical of a compound of Formula C:
wherein R 6 , R 7 , R 8 , R 9 and R 10 are as described above, which process comprises:
reacting the triazine compound of claim 27 with a compound of Formula E:
wherein R 1 , R 2 , R 3 , R 4 and R 5 are as described above, in the presence of a catalyst and at a suitable temperature and pressure, and for a time sufficient to produce a reaction mixture comprising the composition.
30 . A compound of Formula J:
wherein X is a halogen and R 1 , R 2 , R 3 , R 4 , and R 5 are as described above.
31 . A process for preparing a composition comprising at least one triazine compound of Formula A:
wherein Ar 1 and Ar 2 are the same or different, and each independently is a radical of a compound of Formula B:
wherein Y, R 1 , R 2 , R 3 , R 4 and R 5 are as described above, or a radical of a compound of Formula C:
wherein R 6 , R 7 , R 8 , R 9 and R 10 are as described above, which process comprises:
reacting the triazine compound of claim 30 with a compound of Formula F:
wherein R 6 , R 7 , R 8 , R 9 and R 10 are as defined above, in the presence of a catalyst and at a suitable temperature and pressure, and for a time sufficient to produce a reaction mixture comprising the composition.
32 . A process for preparing a composition comprising at least one triazine compound of Formula A:
wherein Ar 1 and Ar 2 are the same or different, and each independently is a radical of a compound of Formula B:
wherein Y, R 1 , R 2 , R 3 , R 4 and R 5 are as described above, or a radical of a compound of Formula C:
wherein R 6 , R 7 , R 8 , R 9 and R 10 are as described above, which process comprises:
reacting the triazine compound of claim 30 with a compound of Formula E:
wherein R 1 , R 2 , R 3 , R 4 and R 5 are as described above, in the presence of a catalyst and at a suitable temperature and pressure, and for a time sufficient to produce a reaction mixture comprising the composition.
33 . A process for preparing a composition comprising at least one triazine compound of Formula I:
wherein X, R 1 , R 2 , R 3 , R 4 , and R 5 , are as described above, which process comprises reacting in the presence of a first catalyst, sufficient amounts of a compound of Formula D:
wherein X is a halogen,
and a compound of Formula E:
wherein R 1 , R 2 , R 3 , R 4 and R 5 are as described above, at a suitable temperature and pressure, and for a time sufficient to form the composition.
34 . A process for preparing a composition comprising at east one triazine compound of Formula J:
wherein X, R 1 , R 2 , R 3 , R 4 , and R 5 , are as described above, which process comprises reacting in the presence of a first catalyst, sufficient amounts of a compound of Formula D:
wherein X is a halogen,
and a compound of Formula E:
wherein R 1 , R 2 , R 3 , R 4 and R 5 are as described above, at a suitable temperature and pressure, and for a time sufficient to form the composition.
35 . A triazine composition comprising a compound of Formula I:
or a compound of Formula J:
or mixtures thereof, wherein X is a halogen and R 1 , R 2 , R 3 , R 4 , and R 5 are as described above.
36 . A process for preparing a composition comprising at least one triazine compound of Formula A:
wherein Ar 1 and Ar 2 are the same or different, and each independently is a radical of a compound of Formula B:
wherein Y, R 1 , R 2 , R 3 , R 4 and R 5 are as described above, or a radical of a compound of Formula C:
wherein R 6 , R 7 , R 8 , R 9 and R 10 are as described above, which process comprises:
(i) reacting in the presence of a first catalyst, sufficient amounts of the composition of claim 35 and one of a compound of Formula E:
wherein R 1 , R 2 , R 3 , R 4 and R 5 are as described above, or a compound of Formula F:
wherein R 6 , R 7 , R 8 , R 9 and R 10 are as described above, in the presence of a catalyst and at a suitable temperature and pressure, and for a time sufficient to produce a reaction mixture comprising the composition.Cited by (0)
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