Ciba-geigy Corporation

Ciba Specialty Chemicals Corporation

Tyler A Stevenson

Ramanathan Ravichandran

Mark S Holt

Roland A Winter

Volker H Von Ahn

Jean-Luc Birbaum

Vien V Toan

Thuy N Phan

Revathi Iyengar

Pascal Hayoz

Robert A Falk

Roger Meuwly

Gregory R Coughlin

Michael Ackerman

Christian Schregenberger

John Francis Oswald

A process for preparing 2-(2,4-dihydroxyphenyl)-4.6-diaryl-s-triazines in three steps starting with cyanuric chloride is described. Step,involves the nucleophilic (basic) displacement of one chlorine atom with a phenolic moiety. Step,involves a Friedel-Crafts reaction using a Lewis acid catalyst (preferably aluminum chloride) to replace the remaining two chlorine atoms with aryl groups such as xylyl. Finally, step,involves replacing the phenolic moiety with resorcinol using either a Lewis acid or protic acid catalyst or combinations thereof. Some additional processes only peripherally related to the three-step process outlined above are also described for the preparation of various s-triazine compounds. The s-triazines prepared are useful as UV absorbers for the stabilization of organic substrates against the adverse effects of actinic light.

Methods for the preparation of tris-aryl-o-hydroxyphenyl-s-triazines

2-(2-Hydroxyphenyl)-2H-benzotriazole UV-absorbers substituted at the 5-position of the benzo ring by a thioether group exhibit enhanced absorption in the near visible range (over 350 nm) allowing said compounds to be particularly effective in protecting polymer systems which are prone to degradation caused by actinic irradiation with wavelengths over 350 nm.

Process for making 5-thio-substituted benzotriazole UV absorbers

Selected s-triazines of formula I ##STR1## where G.sub.1 and G.sub.2 are biphenylyl moieties, are UV absorbers having high thermal stability and surprisingly high extinction coefficients making them of especial interest in stabilizing automotive coatings where such properties are highly valued.

Tris-aryl-s-triazines substituted with biphenylyl groups

The s-triazines of formula I are UV absorbers having high thermal stability and surprisingly high extinction coefficients making them of especial value for stabilizing polymer subsnates, especially automotive coatings. Tris-aryl-s-triazines in which at least one of the aryl groups has an hydroxy group ortho to the point of attachment to the triazine ring are well known UV absorbers. It is also well-known that this class of triszines protect organic polymers from the deleterious effects of exposure to actinic radiation. The instant invention pertains to novel dimetic or oligomeric tris-aryl-s-triazines wherein at least one of the aryl groups is a biphenylyl or substituted biphenylyl moiety. More particularly, the instant invention relates to compounds of formula I ##STR1## wherein G.sub.1, G.sub.2, and E.sub.2 are here-in-below defined.

Tris-aryls-triazines substituted with biphenylyl groups

Tris-aryl-s-triazines of formula VI ##STR1## which contain from one to three resorcinol derived moieties have UV spectra which are red-shifted to the near UV range and provide excellent stabilization to polymeric substrates against the deleterious effects of actinic light.

Compositions stabilized with red-shifted tris-aryl-s-triazines

Tris-aryl-s-triazines of formula VI ##STR1## which contain one or more resorcinol derived moieties have UV spectra which are red-shifted to the near UV range and provide excellent stabilization to polymeric substrates against the deleterious effects of actinic light.

Red-shifted tris-aryl-s-triazines

Tris-aryl-s-triazines of formula V ##STR1## which contain from one one to three resorcinol derived moieties with at least one of said moieties substituted in the 5-position with a group such as, for example, alkyl or phenylalkyl have UV spectra which are red-shifted to the near UV range and provide excellent stabilization to polymeric substrates against the deleterious effects of actinic light.

Red-shifted tris-aryl-S-triazines

Tris-aryl-s-triazines of formula I, II or III ##STR1## which contain from one one to three resorcinol derived moieties with at least one of said moieties substituted in the 5-position with a phenylalkyl group have UV spectra which are red-shifted to the near UV range and provide excellent stabilization to polymeric substrates against the deleterious effects of actinic light.

s-Triazine UV absorbers substituted by a benzotriazolyl or benzophenonyl moiety exhibit unexpectedly improved UV absorption characteristics and outstanding efficacy in protecting organic substances from the deleterious effects of actinic radiation as well as good resistance to loss by volatilization during processing of stabilized compositions at elevated temperatures.

Hybrid s-triazine light stabilizers substituted by benzotriazole or

Tris-aryl-s-triazines which contain from one to three resorcinol derived moieties with at least one of said moieties substituted at the 5-position with an alkyl, phenylalkyl, halogen, thio or sulfonyl group have UV spectra which are red-shifted to the near UV range and provide excellent stabilization to polymeric substrates against the deleterious effects of actinic light. ##STR1##

Red-shifted tris-aryl-s-triazines and compositions stabilized therewith

Tris-aryl-s-triazines which contain from one to three resorcinol derived moieties with at least one of said moieties substituted at the 5-position with an alkyl, phenylalkyl, halogen, thio or sulfonyl group have UV spectra which are red-shifted to the near UV range and provide excellent stabilization to polymeric substrates against the deleterious effects of actinic light.

Compositions stabilized with 5-thio-substituted benzotriazole

Tris-aryl-s-triazine UV absorbers typified by those of formula B or C ##STR1## wherein X and L each possess a sulfur-containing moiety, provide excellent light stability protection to electro coat, base coat or clear coat finishes.

S-triazine UV absorbers substituted by a sulfur-containing moiety

2-(2-Hydroxyphenyl)-2H-benzotriazole UV-absorbers substituted at the 5-position of the benzo ring by a sulfoxide or sulfone group exhibit enhanced absorption in the near visible range (over 350 nm) allowing said compounds to be particularly effective in protecting polymer systems which are prone to degradation caused by actinic irradiation with wavelengths over 350 nm.

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Teaneck, NJ, United States of America

Tyler A Stevenson