Ciba-geigy Corporation

Ciba Specialty Chemicals Corporation

Basf Se Corporation

Ciba Corporation

Joseph E Babiarz

Mervin Gale Wood

Stephen D Pastor

Ramanathan Ravichandran

Glen T Cunkle

Rong Xiong

Joseph Suhadolnik

Robert E Detlefsen

Werner Rutsch

David G Leppard

Roland A Winter

Paul A Odorisio

Deborah DeHessa

Volker H Von Ahn

Mark S Holt

Jacqueline Lau

Andrew B Naughton

Jerome Sanders

James Peter Galbo

Michael P DiFazio

Wanda H Martin

Paul Kondracki

Andrew Brian Naughton

Anthony David Debellis

Deborah Judd

Samuel Evans

Sai Ping Shum

Roger Meuwly

Roswell Easton King

Thelma Spivack

Sterically hindered hydroxy substituted alkoxyamine stabilizer compounds are made water compatible via certain backbones with affinity towards water. The sterically hindered amines are for example of formulae (5)-(7) These compounds are particularly effective in stabilizing aqueous polymer systems against the deleterious effects of oxidative, thermal and actinic radiation. The compounds are effective for example in stabilizing water borne coatings, aqueous inks, aqueous ink jet media and photocured aqueous systems.

Water compatible sterically hindered alkoxyamines and hydroxy substituted alkoxyamines

Sterically hindered hydroxy substituted alkoxyamine stabilizer compounds are made water compatible via certain backbones with affinity towards water. The sterically hindered amines are for example of the formula (8)-(10) These compounds are particularly effective in stabilizing aqueous polymer systems against the deleterious effects of oxidative, thermal and actinic radiation. The compounds are effective for example in stabilizing water borne coatings, aqueous inks, aqueous ink jet media and photocured aqueous systems.

Sterically hindered alkoxyamine and hydroxy substituted alkoxyamine stabilizer compounds are made water compatible via certain backbones with affinity towards water. The sterically hindered amines are for example of the formula where for example E and E' are 2-hydroxycyclohexyloxy, 2-hydroxy-2-methylpropoxy, benzyloxy, methoxy, propoxy, hexyloxy, heptyloxy, octyloxy or cyclohexyloxy, Ris for example &#x2014;NHCHCHOH Cl, &#x2014;NHOAc, &#x2550;NOH, &#x2014;NHCH(CH)COOK, &#x2014;NHCHCHN(CH)OAc, &#x2014;NHCHCHSOK, &#x2014;NHCH(COOK)CHCHSCH, &#x2014;NHCHCOOK, &#x2014;OCH(CH)COOK, &#x2014;OCHCHN(CH)OAc, &#x2014;OCHCHSOK, &#x2014;OCH(COOK)CHCHSCHor &#x2014;OCHCOOK, and where Rcomprises repeating units of &#x2014;(OCHCH)&#x2014;, &#x2014;(OCHCH(CH))&#x2014;, &#x2014;(CHCHCOOH)&#x2014;, &#x2014;(CHC(CH)COOH)&#x2014;, &#x2014;(CHCHCOOCH)&#x2014;, &#x2014;(NHCHCH)&#x2014;, &#x2014;(CHCHOH)&#x2014;, &#x2014;(CHCHCONH)&#x2014; or &#x2014;(CHCH(NHCOH))&#x2014;. These compounds are particularly effective in stabilizing aqueous polymer systems against the deleterious effects of oxidative, thermal and actinic radiation. The compounds are effective for example in stabilizing water borne coatings, aqueous inks, aqueous ink jet media and photocured aqueous systems.

The present invention discloses mono-, bis- and tris-nonylcyclohexylphosphite esters, polyolefin compositions stabilized against the deleterious effects of melt processing, heat aging and exposure to combustion products of natural gas which comprise the nonylcyclohexylphosphite esters as stabilizers, and a process towards stabilizing polyolefin compositions by incorporating in or applying thereto the nonylcyclohexylphosphite esters.

Nonylcyclohexylphosphite ester polyolefin stabilizers

The present invention relates to novel ultraviolet light absorbers of the benzoxazinone, oxanilide, benzylidene malonate, quinazoline and benzotriazole classes. The invention also relates to polymer and photographic compositions stabilized against the deleterious effects of light induced degradation which comprise the novel ultraviolet light absorbers.

Ultraviolet light absorbers

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.

A process for preparing 2H-benzotriazole UV absorbers containing a perfluoroalkyl moiety at the 5-position of the benzo ring, preferably a trifluoromethyl group, involves diazotizing the perfluoroalkyl substituted o-nitroaniline using concentrated sulfuric acid plus sodium nitrite or preferably 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.

Process for the preparation of 5-perfluoroalkyl substituted benzotriazole UV absorbers

An environmentally friendly process for the preparation of the 4-functionalized N&mdash;OR derivatives of 2,2,6,6-tetraalkylpiperidines involves the hydrogen peroxide of the corresponding N&mdash;H compound to form the corresponding N-oxyl derivative, reacting two equivalents of the N-oxyl compound with one equivalent of a compound having an allylic hydrogen, a benzylic hydrogen or an activated methine hydrogen to form one equivalent of the corresponding N&mdash;OH compound and one equivalent of the corresponding N&mdash;OR compound, and recycling the N&mdash;OH compound back to the corresponding N-oxyl compound using hydrogen peroxide or air.

Process for the synthesis of 4-substituted N-&lsqb;(alk-2-en-1-yl)oxy&rsqb;-and N-aralkyloxy-2,2,6,6-tetraalkylpiperidines

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

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

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Amawalk, NY, United States of America

Joseph E Babiarz