Ciba Specialty Chemicals Corporation

Michael Ackerman

Valerio Borzatta

James Peter Galbo

Jean-Pierre Wolf

Nicola Lelli

Piero Piccinelli

Ivan Orban

Pascal Hayoz

Tyler A Stevenson

Roger Meuwly

Christian Schregenberger

John Francis Oswald

Block oligomers containing 1-hydrocarbyloxy-2,2,6,6-tetramethyl-4-piperidyl groups as stabilizers for organic materials

A product obtainable by transferring groups of formula (G-I) being present in a block oligomer having a polydispersity {overscore (M)}w/{overscore (M)}n of 1 to 1.7 and corresponding to formula (I) to groups of formula (Gu-II), wherein R is a hydrocarbyl radical or &mdash;O&mdash;R is oxyl; said transfer is carried out by reaction of the block oligomer with a hydroperoxide in a hydrocarbon solvent in the presence of a peroxide decomposing catalyst; n is a number from 2 to 14; R is for example C -C alkylene; A is for example &mdash;N(R )(R ); R and R are for example C -C alkyl; R is preferably a group of formula (G-I) and B and B* have one of the meanings given for A; with the proviso that in the individual recurrent units of formula (I), each of the radicals B, R and R has the same or a different meaning. The products are useful as light stabilizers, heat stabilizers and oxidation stabilizers for organic materials, in particular synthetic polymers.

Compounds of formula (I), in which the polydispersity Mw/Mn is for example 1; n is 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14 the radicals R,are for example C,-C,alkyl or C,-C,cycloalkyl; R,is for example C,alkylene; the radicals A and B* are independently of one another &mdash;OR,, &mdash;N(R,)(R,) or a group of formula (II); R,, R,and R,, which are identical or different, are for example hydrogen or C,-C,alkyl, or &mdash;N(R,)(R,) is additionally a group of formula (III) with Y being &mdash;0&mdash;, &mdash;CH,&mdash;, &mdash;CH,, &mdash;CH,&mdash; or >N&mdash;CH,; X is &mdash;0&mdash; or >N&mdash;R,; R,is for example hydrogen or C,alkyl; R is preferably a group of formula (IV); and B has one of the meanings given for A; with the proviso that in the individual recurrent units of formula (I), each of the radicals B, R, R,and R,has the same or a different meaning. The indicated compounds are useful as light stabilizers, heat stabilizers and oxidation stabilizers for organic materials, in particular synthetic polymers.

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

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Michael Ackerman