Cytec Technology Corporation

Ciba Specialty Chemicals Corporation

Russell C Cappadona

Ram Baboo Gupta

Dennis John Jakiela

Venkatrao K Pai

Sampath Venimadhavan

Hargurpreet Singh

Mark Paterna

Al Wagner

It has been now surprisingly discovered after extensive research that 2-halo-4,6-bisaryl-1,3,5-triazine can be prepared with unprecedented selectivity, efficiency, mild conditions, and in high yield by the reaction of cyanuric halide with aromatics in the presence of at least one Lewis acid and at least one reaction promoter. This reaction is also unprecedently general as a variety of aromatics can be used to produce a wide selection of 2-halo-4,6-bisaryl-1,3,5-triazines. The novel approach includes the use of the reaction promoters in combination with at least one Lewis acid under certain reaction conditions to promote the formation of 2-halo-4,6-bisaryl-1,3,5-triazine compounds from cyanuric halide. Preferably, the Lewis acids and reaction promoters are combined to form a complex 2-Halo-4,6-bisaryl-1,3,5-triazines are key intermediates for making 2-(2-oxyaryl)-4,6-bisaryl-1,3,5-triazine class of UV absorbers.

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

It has been now surprisingly discovered after extensive research that 2-halo-4,6-bisaryl-1,3,5-triazine can be prepared with unprecedented selectivity, efficiency, mild conditions, and in high yield by the reaction of cyanuric halide with aromatics in the presence of at least one Lewis acid and at least one reaction promoter. This reaction is also unprecedently general as a variety of aromatics can be used to produce a wide selection of 2-halo-4,6-bisaryl-1,3,5-triazines. The novel approach includes the use of the reaction promoters in combination with at least one Lewis acid under certain reaction conditions to promote the formation of 2-halo-4,6-bisaryl-1,3,5-triazine compounds from cyanuric halide. Preferably, the Lewis acids and reaction promoters are combined to form a complex. 2-Halo-4,6-bisaryl-1,3,5-triazines are key intermediates for making 2-(2-oxyaryl)-4,6-bisaryl-1,3,5-triazine class of UV absorbers.

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

The invention relates generally to pyrimidines and triazines ultraviolet light absorbers containing a phenolic aromatic group(s) and a non-phenolic aromatic group(s) and the use thereof to protect against degradation by environmental forces, inclusive of ultraviolet light, actinic radiation, oxidation, moisture, atmospheric pollutants, and combinations thereof. The new class of pyrimidines and triazines includes two (one) non-phenolic aromatic groups with hydrocarbyl groups that are ortho to each other and one (two) resorcinol or substituted resorcinol group attached to a triazine or pyrimidine ring. The pyrimidines and triazines may be included in a polymeric structure. A method for stabilizing a material by incorporating the novel pyrimidines and triazines is also disclosed.

Non-yellowing ortho-dialkyl aryl substituted triazine ultraviolet light absorbers

This invention relates generally to phenyl ether substituted triazines compounds and compositions containing same and their use to protect against degradation by environmental forces. A method for stabilizing a material by incorporating such triazines is also disclosed.

Phenyl ether-substituted hydroxyphenyl triazine ultraviolet light absorbers

The present invention relates to novel red-shifted UV absorbers comprising 1,3,5-triazine structures containing a 2-naphthol-derived substituent. The present invention also relates to a method for stabilizing a material by incorporating into such material, e.g., organic material, the novel red-shifted triazine compounds in an amount effective to stabilize the material against the effects of actinic radiation.

Red-shifted triazine ultravioletlight absorbers

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

This invention relates to a novel, efficient, economic and general-purpose process for isolating monophenolic-bisaryl triazine compounds from polyphenolic-triazines compounds and other impurities. More specifically, this invention relates to a process for isolating the monophenolic-bisaryl triazine compounds by contacting it with a base, an alcohol or a hydrocarbon solvent.

Process for isolation of monophenolic-bisaryl triazines

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.

Process for making 2-hydroxy-4-alkoxyphenyl or 2,4-dihydroxyphenyl substituted 1,3,5-triazine UV absorbers

The invention relates to a novel process for making 2-(2-hydroxy-4-alkoxyphenyl)-4,6-bisaryl-1,3,5-triazine and 2-(2,4-dialkoxyphenyl)-4,6-bisaryl-1,3,5-triazine compounds directly from 2-chloro-4,6-bisaryl-1,3,5-triazine compounds with 3-alkoxyphenol, 1,3-dialkoxylbenzene compounds or mixtures thereof. The reaction step to prepare 2-chloro-4,6-bisaryl-1,3,5-triazines from the reaction of cyanuric chloride with substituted aromatic compounds can be combined with the addition reaction of 3-alkoxyphenol or 1,3-dialkoxylbenzene in a two-step, one-pot process. The 2-(2-hydroxyl-4-alkoxyphenyl)-4,6-bisaryl-1,3,5-triazine, and 2-(2,4-dialkoxyphenyl)-4,6-bisaryl-1,3,5-triazine compounds, are useful to stabilize materials against damage by light, heat, and oxygen, and as stabilizers for organic material, or mixtures thereof.

Process for making 2-(2-hydroxy-4-alkoxyphenyl)-4,6-bisaryl-1,3,5-triazines

Provided is a new process for the preparation of compositions containing at least one triazine ultraviolet light absorber.

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Norwalk, CT, United States of America

Russell C Cappadona