Ciba Specialty Chemicals Corporation

Deborah DeHessa

Mervin Gale Wood

Joseph Suhadolnik

Andrea R Smith

Andrew B Naughton

Stephen D Pastor

Anthony DeBellis

Robert E Detlefsen

Ramanathan Ravichandran

Joseph E Babiarz

Jacqueline Lau

Rong Xiong

Jerome Sanders

Stephen Mark Andrews

Douglas Wayne Horsey

Anunay Gupta

Luther A R Hall

Sai Ping Shum

Compounds of formula I or II where R is an aryl moiety, such as phenyl, naphthyl or biphenylyl, or is phenyl substituted by one or more trifluoromethyl, bromo or cyano, and Eand Eare independently hydrogen, alkyl, aralkyl and the like are prepared by reaction of a benzotriazole substituted on the 5-position of the benzo ring by a halogen atom with a arylboronic acid or ester in the presence of a transition-metal catalyst, such as palladium (II) diacetate. The benzotriazole compounds of formula I are particularly efficacious as stabilizers for automotive coatings and candle wax.

Substituted 5-aryl-2-(2-hydroxyphenyl)-2H-benzotriazole UV absorbers, compositions stabilized therewith and process for preparation thereof

Benzotriazole UV absorbers substituted with a ultra long ester or amide moiety wherein the ester or amide group is a hydrocarbyl group of 25 to 100 carbon atoms or is a group of alkyl of 25 to 100 carbon atoms interrupted by 5 to 39 oxygen atoms and terminated with an omega-OH or an omega-OR group exhibit excellent stabilization efficacy while they concomitantly do not bloom when incorporated into polyolefin films. These benzotriazole UV absorbers also provide excellent protection to white, dyed, dipped, unscented and/or scented candle wax from discoloration and degradation.

Bloom-resistant benzotriazole UV absorbers and compositions stabilized therewith

where R is an aryl moiety, such as phenyl, naphthyl or biphenylyl, or is phenyl substituted by one or more trifluoromethyl, bromo or cyano, and Eand Eare independently hydrogen, alkyl, aralkyl and the like are prepared by reaction of a benzotriazole substituted on the 5-position of the benzo ring by a halogen atom with a arylboronic acid or ester in the presence of a transition-metal catalyst, such as palladium (II) diacetate. The benzotriazole compounds of formula I are particularly efficacious as stabilizers for automotive coatings and candle wax.

Substituted 5-aryl-2-(2-hydroxyphenyl)-2h-benzotriazole UV absorbers, compositions stabilized therewith and process for preparation thereof

Provided is a process for preparing 2H-benzotriazole UV absorbers containing a perfluoroalkyl moiety at the 5-position of the benzoic ring, for example a trifluoromethyl group, which involves digitizing the perfluoroalkyl substituted o-nitroaniline using concentrated sulfuric acid plus sodium nitrite or nitrosylsulfuric acid to form the corresponding monoazobenzene intermediate via the diazonium salt intermediate which is reduced to the corresponding 5-perfluoroalkyl substituted 2H-benzotriazole UV absorber compound by conventional reduction means. Also provided is a novel one-pot, multiphase reaction for the preparation of 2(2-nitrophenylazo) substituted phenols, which are precursors for 2H-benzotriazole UV absorbers.

Processes for the preparation of benzotriazole UV absorbers

Provided is a process for preparing 2H-benzotriazole UV absorbers containing a perfluoroalkyl moiety at the 5-position of the benzo ring, for example a trifluoromethyl group, which involves diazotizing the perfluoroalkyl substituted o-nitroaniline using concentrated sulfuric acid plus sodium nitrite or nitrosylsulfuric acid to form the corresponding monoazobenzene intermediate via the diazonium salt intermediate which is reduced to the corresponding 5-perfluoroalkyl substituted 2H-benzotriazole UV absorber compound by conventional reduction means. Also provided is a novel one-pot, multiphase reaction for the preparation of 2(2-nitrophenylazo) substituted phenols, which are precursors for 2H-benzotriazole UV absorbers.

White, dyed, dipped, unscented and/or scented candle wax is effectively stabilized against discoloration and fading by the incorporation therein of a piperazindione in combination with a UV absorber and/or an antioxidant.

Candle wax stabilized with piperazindiones

White, dyed, dipped, unscented and/or scented candle wax is effectively stabilized against discoloration and fading by the incorporation therein of an s-triazine UV absorber plus a classic hindered amine and/or an antioxidant.

Candle wax stabilized with s-triazines/hals

White, dyed, dipped, unscented and/or scented candle wax is effectively stabilized against discoloration and fading by the incorporation therein of an imidazolidine in combination with a UV absorber and/or an antioxidant.

Candle wax stabilized with imidazolidines

White, dyed, dipped, unscented and/or scented candle wax is effectively stabilized against discoloration and fading by the incorporation therein of a morpholinone in combination with a UV absorber and/or an antioxidant.

Candle wax stabilized with morpholinones

White, dyed, dipped, unscented and/or scented candle wax is effectively stabilized against discoloration and fading by the incorporation therein of a piperazinone in combination with a UV absorber and/or an antioxidant.

Candle wax stabilized with piperazinones

White, dyed, dipped, unscented and/or scented candle wax is effectively stabilized against discoloration and fading by the incorporation therein of an oxazolidine in combination with a UV absorber and/or an antioxidant.

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Poughkeepsie, NY, United States of America

Deborah DeHessa