Ciba-geigy Corporation

Ciba Specialty Chemicals Corporation

Mark S Holt

Ramanathan Ravichandran

Tyler A Stevenson

Roland A Winter

Volker H Von Ahn

David G Leppard

Joseph E Babiarz

Jean-Luc Birbaum

Vien V Toan

Thuy N Phan

James Peter Galbo

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

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.

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

Soluble and thermally stable benzotriazole UV absorbers typified by those of formula I ##STR1## where R.sub.1 is hydrogen or chloro, R.sub.2 is alkyl or --CH.sub.2 CH.sub.2 COOR.sub.4 where R.sub.4 is hydrogen, alkyl or alkyl substituted with hydroxyl, and R.sub.3 is .alpha.-cumyl, provide excellent light stability protection to electro coat, base coat or clear coat finishes. The new soluble, crystalline form of 2-(2-hydroxy-3-.alpha.-cumyl-5-tert-octylphenyl)-2H-benzotriazole is particularly effective.

2-(2-hydroxy-3-.alpha. cumyl-5-tert nonyl or dodecyl phenyl)-2H-

Crystalline form of

Electro coat/base coat/clear coat finishes stabilized with soluble and

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

2-(2-hydroxy-3-.alpha.-cumyl-5-nonylor 5-dodecylphenyl)-2H-benzotriazole

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.

Compositions stabilized with 5-sulfonyl-substituted benotriazole

Tris-aryl-s-triazine UV absorbers typified by those of formula A or B ##STR1## provide excellent light stability protection to electro coat, base coat or clear coat finishes.

Electro coat/base coat/clear coat finishes stabilized with S-triazine UV

1-Hydrocarbyloxy-2,2,6,6-tetramethylpiperidine derivatives of s-triazines having functional groups such as hydroxy, amino, carboxy, epoxy, isocyanate or the like present are capable of chemically bonding with polymer substrates having anhydride, epoxide, alkoxymethylmelamine or isocyanate moieties present. This chemical bonding prevents migration or loss of the stabilizer during subsequent processing or end-use application of the stabilized polymer.

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West Nyack, NY, United States of America

Mark S Holt