Cytec Technology Corporation

Ciba Specialty Chemicals Corporation

Dennis John Jakiela

Ram Baboo Gupta

Russell C Cappadona

Venkatrao K Pai

Sampath Venimadhavan

Gottfried Haacke

Thomas P Sassi

Robert G Fischer

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

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

This invention relates generally to para-tertiary alkyl phenyl substituted pyrimidines and triazines 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 para-tertiary alkyl phenyl substituted pyrimidines and triazines includes two tertiary alkylated phenyl groups, and a resorcinol or substituted resocinol group attached to the triazine or pyrimidine ring. These materials may, under the appropriate circumstances, be bonded to formulations comprising coatings, polymers, resins, organic compounds and the like via reaction of the bondable functionality with the materials of the formulation. A method for stabilizing a material by incorporating such para-tertiary alkyl phenyl substituted pyrimidines and triazines is also disclosed.

Non-yellowing part-tertiary-alkyl phenyl substituted triazine and pyrimidine ultraviolet light absorbers

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

This invention relates generally to a new class of benzocycle-substituted pyrimidines and triazines and the use thereof to protect coatings, polymers and organic compounds against degradation by environmental forces, inclusive of ultraviolet light, actinic radiation, oxidation, moisture, atmospheric pollutants and combinations thereof. The new class of benzocycle-substituted pyrimidines and triazines comprises a benzocycle attached to the triazine or pyrimidine ring, and preferably an additional aryl ring containing a hydroxyl group, either free or blocked to form a latent stabilizer, ortho- to the point of attachment to the triazine or pyrimidine ring.

Benzocycle-substituted triazine and pyrimidine ultraviolet light absorbers

This invention relates generally to amido or carbamate substituted trisaryl-1,3,5-triazines 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 trisaryl-1,3,5-triazines comprises an aryl ring attached to the triazine ring (and preferably an aryl ring containing a hydroxyl group, either free or blocked to form a latent stabilizer, ortho- to the point of attachment to the triazine ring) substituted with a group comprising a bondable amido/carbamate containing group para- to the point of attachment to the triazine ring. These materials may, under the appropriate circumstances, be bonded to formulations comprising coatings, polymers, resins, organic compounds and the like via reaction of the bondable functionality with the materials of the formulation. A method for stabilizing a material by incorporating such amido or carbamate substituted trisaryl-1,3,5-triazines is also disclosed.

Trisaryl-1,3,5-triazine ultraviolet light absorbers

The present invention relates to novel bondable trisaryl-1,3,5-triazines containing active (acidic) hydrocarbons and the use thereof as an ultraviolet light absorber. The presently claimed compounds are particularly useful, either alone or in combination with other additives, including other ultraviolet light absorbers and stabilizers, in stabilizing polymers and other materials from degradation by environmental forces such as actinic radiation (ultraviolet light), oxidation, moisture, atmospheric pollutants and combinations thereof.

This invention relates generally to red-shifted trisaryl-1,3,5-triazines 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 trisaryl-1,3,5-triazines comprises an aryl ring attached to the triazine ring &lsqb;and preferably an aryl ring containing a hydroxyl group, either free or blocked to form a latent stabilizer, ortho- to the point of attachment to the triazine ring (2-position) and a hydroxyl group or a moiety joined by an ether linkage para- to the point of attachment to the triazine ring (4-position)&rsqb; substituted at the 3-position or disubstituted at the 3- and 5-positions with a group comprising an amide and/or an amine. These materials may be incorporated into formulations comprising coatings, polymers, resins, organic compounds and the like. A method for stabilizing a material by incorporating such red-shifted trisaryl-1,3,5-triazines is also disclosed.

Red-shifted trisaryl-1,3,5-triazine ultraviolet light absorbers

The present invention relates to novel carbamate containing trisaryl-1,3,5-triazines and the use thereof as an ultraviolet light absorber. In particular, the presently claimed compounds comprise a carbamate triazine polymer which is particularly useful, either alone or in combination with other additives, including other ultraviolet light absorbers and stabilizers, in stabilizing a polymeric film or molded article from degradation due to exposure to actinic radiation.

Poly-trisaryl-1,3,5-Triazine carbamate ultraviolet light absorbers

This invention relates generally to benzocycle-substituted pyrimidines and triazines 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 benzocycle-substituted pyrimidines and triazines comprises a benzocycle attached to the triazine or pyrimidine ring, and preferably an additional aryl ring containing a hydroxyl group, either free or blocked to form a latent stabilizer, ortho- to the point of attachment to the triazine or pyrimidine ring. These materials may, under the appropriate circumstances, be bonded to formulations comprising coatings, polymers, resins, organic compounds and the like via reaction of the bondable functionality with the materials of the formulation. A method for stabilizing a material by incorporating such benzocycle-substituted pyrimidines and triazines is also disclosed.

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.

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Orange, CT, United States of America

Dennis John Jakiela