Ciba-geigy Corporation

Ciba Specialty Chemicals Corporation

Basf Se Corporation

Vien V Toan

David G Leppard

Pascal Hayoz

Andreas Valet

Jean-Luc Birbaum

Gerhard Rytz

Ramanathan Ravichandran

Hugh Stephen Laver

Tyler A Stevenson

Mark S Holt

Christophe Bulliard

Thuy N Phan

Norbert Wurms

Eric Vieira

Mario Slongo

Helmut Luther

Dietmar H&uuml;glin

Dieter Reinehr

Georges Metzger

Adalbert Braig

Thomas Schäfer

Roger Meuwly

Michela Bonora

Roland A E Winter

Stéphane Biry

Thomas Vogel

Peter Michaelis

Ronald Salath&eacute;

Walter Knupp

Norbert W Urms

The instant invention relates to novel tris(hydroxyphenyl)triazines coating compositions, for instance automotive coating compositions, and to novel tris(hydroxyphenyl) triazines UV-absorbers having a long wavelength sifted absorption spectrum with significant absorbance up to 420 nm. Further aspects of the invention are a UV stabilized composition containing the novel UV-absorbers, a process for the stabilization of organic materials and coatings and the use of the compounds as UV-light stabilizers for organic materials and coatings.

Tris(hydroxyphenyl) triazines

Novel compounds of formula I are described whereinE corresponds to the formula or to the formula and the radicals R, R, R, R, R', R&#x2032;and R&#x2032;are as defined in claim. Compounds of formula I are suitable for stabilizing organic material, especially plastics materials, surface-coatings, cosmetic preparations, sun protection agents or photographic material, against damage by light, oxygen and/or heat.

Naphthyltriazines as stabilizers for organic material

Triazine, benzotriazole and benzophenone derivatives which are substituted or bridged with polyoxyalkylene groups, according to claim 1, and their use as UV absorbers, especially in photographic materials, in inks, including inkjet inks and printing inks, in transfer prints, in paints and varnishes, organic polymeric materials, plastics, rubber, glass, packaging materials, in sunscreens of cosmetic preparations and in skin protection compositions.

Polyoxyalkylene substituted and bridged benzotriazole derivatives

Dimeric light stabilizers for polyolefines and polyolefine copolymers

Process for the preparation of low chloride stabilizers

Triazine, benzotriazole and benzophenone derivatives which are substituted or bridged with polyoxyalkylene groups, according to claim and their use as UV absorbers, especially in photographic materials, in inks, including inkjet inks and printing inks, in transfer prints, in paints and varnishes, organic polymeric materials, plastics, rubber, glass, packaging materials, in sunscreens of cosmetic preparations and in skin protection compositions.

Polyoxyalkylene substituted and bridged triazine, benzotriazole and benzophenone derivatives as UV absorbers

A description is given of compounds of the formula I

Hydroxyphenyltriazines

Hydroxyphenyl triazines

There are described compounds of formula A wherein

Compositions based on synthetic organic polymers or prepolymers are effectively stabilized against the damaging effects of light, oxygen and/or heat by addition of a compound of the formula I ##STR1## in which Z is a group of one of the formulae II or III, ##STR2## R.sub.7 and R.sub.17, independently of one another, are a radical of one of the formulae IV, V and VI ##STR3## and the remaining symbols are as defined in claim 1.

The invention relates to novel 2-hydroxyphenyltriazines and to homopolymers and copolymers obtainable therefrom, as described in greater detail in claims 1 and 5; the novel compounds can be used as UV absorbers in or for organic materials.

Polymeric compounds derived from 2-hydroxy-phenyl-s-triazines

Compounds of the formula I ##STR1## in which R.sub.1 and R.sub.5, independently of one another, are C.sub.1 -C.sub.12 alkyl; R.sub.2, R.sub.3 and R.sub.4, independently of one another, are H; C.sub.1 -C.sub.12 alkyl; C.sub.2 -C.sub.6 alkenyl; C.sub.1 -C.sub.12 alkoxy; C.sub.2 -C.sub.18 alkenyloxy; halogen; trifluormethyl; C.sub.7 -C.sub.11 phenylalkyl; phenyl; phenyl which is substituted by C.sub.1 -C.sub.18 alkyl, C.sub.1 -C.sub.18 alkoxy or halogen; phenoxy; or phenoxy which is substituted by C.sub.1 -C.sub.18 alkyl, C.sub.1 -C.sub.18 alkoxy or halogen; the two radicals R.sub.7 are identical or different and are hydrogen or C.sub.1 -C.sub.18 alkyl; or are C.sub.1 -C.sub.18 alkyl which is substituted by OH, C.sub.1 -C.sub.18 alkoxy, C.sub.3 -C.sub.6 alkenyloxy, halogen, --COOH, --COOR.sub.8, --CONH.sub.2, --CONHR.sub.9, --CON(R.sub.9)(R.sub.10), --NH.sub.2, --NHR.sub.9, --N(R.sub.9)(R.sub.10), --NHCOR.sub.11, --CN, --OCOR.sub.11, phenoxy and/or phenoxy which is substituted by C.sub.1 -C.sub.18 alkyl, C.sub.1 -C.sub.18 alkoxy or halogen; or the radicals R.sub.7 are C.sub.3 -C.sub.50 alkyl which is interrupted by --O-- and may be substituted by OH, phenoxy or C.sub.7 -C.sub.18 alkylphenoxy; or the radicals R.sub.7 are C.sub.3 -C.sub.6 alkenyl; glycidyl; C.sub.5 -C.sub.12 cycloalkyl; C.sub.5 -C.sub.12 cycloalkyl which is substituted by OH, C.sub.1 -C.sub.4 alkyl oder --OCOR.sub.11 ; C.sub.7 -C.sub.11 phenylalkyl which is unsubstituted or substituted by OH, Cl or CH.sub.3 ; C.sub.4 -C.sub.14 alkenyl which is substituted by OH or --OCOR.sub.11 ; --CO--R.sub.12 or --SO.sub.2 --R.sub.13 ; and R.sub.8 to R.sub.14 are as defined in claim 1, are highly suitable for stabilizing organic material, including photographic recording material.

Bisresorcinyltriazines

s-Triazine UV absorbers of formula I ##STR1## where R.sub.1 is ##STR2## --CH.sub.2 --C(.dbd.CH.sub.2)--R.sub.10, --(CH.sub.2).sub.p --SiR.sub.11 R.sub.11 '--CH.dbd.CH.sub.2, --C(.dbd.O)--(CH.sub.2).sub.q --CH.dbd.CH.sub.2 or --C(.dbd.O)--O--CH.sub.2 --C(.dbd.CH.sub.2)--R.sub.10 ; and E.sub.1 and E.sub.2 are phenyl groups which may be unsubstituted or substituted with a variety of substituents including inter alia alkyl, OH and R.sub.1 ; are polymerizable and are effective stabilizers for a variety of polymeric and other organic substrates.

2-Hydroxyphenyl-s-Triazines substituted with ethylenically unsaturated

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

The invention relates to compounds of the formula I ##STR1## in which n is 1 or 2, A is CH or a nitrogen atom, and the other radicals R.sup.1 to R.sup.25 are as defined in claim 1. The compounds of the formula I can advantageously be employed for stabilizing organic material against the harmful effect of light, oxygen and/or heat.

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Lentigny, Switzerland

Vien V Toan