MXPA97006168A - Tris-aril-s-triazinas substituted with bifenil groups - Google Patents

Abstract

s-Triazines selected from formula I (see Formula) wherein G1 and G2 are biphenyl portions, are UV absorbers having high thermal stability and surprisingly high extinction coefficients being of special interest to stabilize automotive coatings where these properties are highly valios

Description

TRIS-ARIL-S-TRIAZINES SUBSTITUTED WITH GRUPQS BIFEI W The s-triazines of formula I are absorbers of ultraviolet light (UV) that have high thermal stability and surprisingly high extinction coefficients making them of special value to stabilize polymer substrates, especially automotive coatings. The tris-aryl-s-triazines wherein at least one of the aryl groups have a hydroxy ortho group at the connection point to the triazine ring are well known UV absorbers. It is also well known that this class of triazines protects organic polymers from the harmful effects of exposure to actinic radiation. For purposes of this application, 2,4-dilihydroxyphenyl groups in a s-triazine ring may be referred to as resorcinol groups. The numbering system used in the resorcinol group is outlined as follows: The patents of the U.S.A. Nos. 3,118,887 and 3,268,474 describe the protection of plastic and resinous compositions from UV light by the incorporation of one or more compounds of the tris-aryl-s-triazine class. The first patent claims 2,4,6-tris- (2,4-dihydroxy-phenyl) -s-triazine and 2,4,6-tris (2-hydroxy-4-alkoxyphenyl) -s-triazine. A tris-5-alkyl-resorcinol-s-triazine is prepared but not tested or claimed. The patent of the U.S.A. No. 3,268,474 claims the composition of a polymeric material of a tris-aryl-s-triazine having at least one ortho-hydroxyphenyl group and which can also be substituted in each of three aryl rings by alkyl, alkoxy, halo, etc. , with a total of up to three substituents in each ring. Preferred substitution patterns are not given. There are specific claims for compositions that include tris (2-hydroxy-4-alkoxy-phenyl) -s-triazines and 2,4-bis- (2,4-dimethylphenyl) -6- (2-hydroxy-4-octyloxy-phenyl) -s-triazine. Again, an example of a tris-alkylresorcinol-s-triazine is given, but it is not tested and its composition with a polymer is not claimed. The patent of the U.S.A. No. 3,242,175 claims bis-resorcinol-tris-aryl-s-triazine without substitution in the resorcinol rings. The patent of the U.S.A. No. 3,244,708 claims mono-, bis- or tris-resorcinol-tris-aryl-s-triazine without substitution in the resorcinol rings. A Mar ush structure in the introduction of the patent refers to mono-resorcinol-tris-aryl-s-triazines which may also be substituted in the resorcinol ring by one or two combinations of hydroxy, halogen, alkyl, alkoxy, phenyl or phenylalkyl . Preferred substitution patterns nb are mentioned and none of these compounds is synthesized or tested. The patents of the U.S.A. Nos. 4,619,956 and 4,740,542 describe the use of synergistic amounts of tris-aryl-s-triazines and hindered amine light stabilizers in polymeric film coatings or molded articles against the action of light, moisture and oxygen. The tris-aryl-s-triazines referred to in these patents are those described in the patent of E.U.A. No. 3,268,474. The preferred s-triazine is 4,6-bis- (2,4-dimethylphenyl) -2- (2, -dihydroxyphenyl) -s-triazine or 4, β-bis- (2,4-dimethylphenyl) -2- ( 2-hydroxy-4-octyloxyphenyl) -s-triazine. A Markush structure in the patents describes tris-aryl-s-triazines with at least one hydroxy group ortho to the point of connection to the triazine ring and which may have up to three substituents in each of three aryl rings. These substitutes include alkyl, alkoxy, halo, etc. Preferred substitution patterns are not given, nor are prepared or tested substitutes in a resorcinol ring. Additionally, while these two patents generically describe mono-s-triazines substituted inter alia with biphenylyl groups, no specific mono-s-triazines having biphenylyl groups are described and the high beneficial extinction coefficients that are provided by these groups are not describe equally.

The E.P. No. 444,323 claims tris-aryl-s-triazines highly soluble, the process for its preparation and its composition with an organic solvent. A specific triazine mentioned as useful in this process is 2- (2,4-dihydroxyphenyl) '4,6-bis- (2,4-di-methylphenyl) -s-triazine. The tris-aryl-s-triazines claimed in this application are based on those described in U.S. Pat. No. 3,268,474. The preferred triazines are s-triazines based on ono-resorcinol-tris-raryl. The preferred Markush group shows that the resorcinol ring can also be substituted at the 5-position with alkyl groups. However, substitution effects in this position are not mentioned and none of these compounds is prepared or tested. The request of E.P. No. 483,488 and the US patent. No. 5,461,151 claim the synergistic stabilizing composition comprising a tris-aryl-s-triazine and a hindered amine and the method for stabilizing a polymer by incorporating said composition. Again, the triazines claimed in the Compositions are based on those described in U.S. Pat. No. 3,268,474. The preferred triazines are s-triazines based on bis-xylyl-resorcinol. The body of the application shows a Markush structure of a s-triazine based on mono-resorcinol-tris-aryl, which can also be further substituted at the 5-position of the resorcinol ring with alkyl groups. However, triazines are not prepared or tested with this additional substitution in the resorcinol ring. The patents of the U.S.A. Nos. 4,826,978 and 4,962,142 describe a class of tris-aryl-s-triazines useful as ultra-violet filters for polymers, including coatings. The triazines are based on bis-resorcinol-phenyl-s-triazines with groups that withdraw substituted electrons in the phenyl group. No greater substitution is reported in the resorcinol groups. The patent of the U.S.A. No. 5,106,891 claims coating composition containing as the UV absorber, a mixture of at least one 2-hydroxyphenylbenzotriazole and at least one 2-hydroxyphenyltriazine. The triazines described are based on mono-resorcinol-tris-aryl-s-triazines, with the preferred structure based on bis-xylyl-resorcinol-s-triazine. The Markush structure describes that aryl groups can be substituted with up to three hydroxyl, halogenomethyl, alkyl, alkoxy or halogen or combinations thereof. Structures are therefore described for tris-aryl-s-triazines with substituted resorcinol groups, but preferred substitution patterns are not described and these compounds are not prepared or tested. The E.P. Np. 434,608 claims an organic material that has stabilized against damage by light, heat and oxygen and that contains a combination of a hindered amine and an o-hydroxyphenyl-s-triazine triazine alone, the procedure to stabilize an organic material when incorporating the combination of a hindered amine and triazine or triazine alone, novel o-hydroxyphenyl-s-triazines and the use of the novel s-triazines as stabilizers for organic materials. Specifically mentioned organic materials are coating binders and radiation curable coating materials. The preferred triazines are s-triazines based on mono-resorcinol-tris-aryl without further substitution in the resorsinol ring. A Markush structure covering tris-aryl-s-triazines with one or two resorcinol groups substituted with alkyl or halo is claimed. Preferred substitution patterns are not given, and compounds with substituted resorcinol rings are not prepared or tested. The E.P. No. 442,847 claims a coating composition containing a binder, a curing agent and a tris-aryl-s-triazine as a stabilizing agent against damage by light, heat and oxygen. The use of this composition for automotive coatings is specifically mentioned. Preferred triazines for use in this composition are s-triazines based on mono-resorcinol-tris-aryl without substitution in the resorcinol ring. A Markush structure is described in the claims section, which includes tris-aryl-s-triazines with one or two resorcinol groups which may also be substituted by alkyl or halogen. Preferred substitution patterns are not given, and compounds with substituted resorcinol rings are not prepared or tested. The patent of the U.S.A. No. 5,354,794 claims a polymer film composition comprising an electrocoat primer, a color coating in adhesion to the electrocoat, a clear coating in addition to the color coating and a UV absorber of tris-aryl-s-triazine either in the color coating or the clear coating or both. It is noted that a particular subgenre of tris-aryl-s-triazines those based on bis- and tris-resorcinol-tris-aryl + -s-triazines, are especially effective in stabilizing said coating system. A Markush structure in the composition claims describes bis- and tris ^ -resorcinol-tris-aryl-s-triazines which may be substituted in the resorcinol rings by an alkyl of 1 to 6 carbon atoms. Specific substitution patterns are not discussed. An example of the preparation of 2,4,6-tris- (2,4-dihydroxy-5-he? Ilphenyl) -s-triazine is given, but this compound is not tested. The patent of the U.S.A. No. 5,298,067 claims a coating material stabilized with monomers or dimers of s-triazines based on mono-resorcinol-tris-aryl alone or in combination with a hindered amine or a hydroxyphenylbenzo-triazole, and the method of stabilizing a coating material at incorporate these s-triazines. No greater substitution is reported in the resorcinol groups. A specifically mentioned coating material is an automotive lacquer. The E.P. No. 165,608 describes s-triazines including a class of tris-aryl-s-triazines, the process for their preparation and their method for use as UV absorbers in organic materials, especially color photographic materials. Tris-aryl-s-triazines described include those with one to three resorcinol groups which may be substituted with alkyl, alkoxy, hydroxy or alkyl or phenylcarbonyl. Preferred substitution patterns are not described. Examples are given for bis-resorcinol-tris-aryl-s-triazines with resorcinol substituted by methyl at position-3, at position-6 by hydroxy, methoxy and methyl and at position-5 by acetyl. The patent of the U.S.A. No. 3,843,371 claims photographic material containing a tris-aryl-s-triazine as a stabilizing agent against UV radiation. A Markush structure in the claims of this patent includes bis-resorcinol-tris-aryl-s-triazines which may have an alkyl substituent at the 6-position of one of the resorcinol rings. Preferred triazines are s-triazines based on bis-resorcinol-tris-aryl without further substitution in the resorsinol rings. A Markush structure in the body of the patent discloses tris-aryl-s-triazines which may have one or two resorcinol groups which may be substituted with halogen, hydroxyl, alkyl, also xyl, phenyl, phenoxy, cycloalkyloxy, ets. Preferred substitution patterns are not discussed and compounds with substituted resorcinol groups are not prepared or tested. The request E.P. No. 468,921 claims aqueous dispersions of s-triazines with at least one anionic or nonionic compound. The Markush structure in the claims section includes tris-aryl-s-triazines that possibly have a resorcinol ring substituted by alkyl or halogen. The substitution pattern is not specified. Preferred triazines include s-triazines based on mono-resorcinol-tris-aryl without substitution in the resorcinol ring and are the only exemplified s-triazines. The patent of the U.S.A. No. 4,831,068 claims a process for stabilizing dyes in polyester fiber materials with a UV s-triazine absorbent and the polyester fiber material treated by this process. The Markush structure and the preferred triazines are the same as in the application E.P. No. 468921 Again, only the s-triazines of the preferred type are illustrated in the examples. The patent of the U.S.A. No. 4,950,304 claims the process for neutralizing or suppressing the fluorescence of natural or synthetic polyamide substrates treated with bleaching agents. The process comprises applying to the substrates a liquor containing a hydroxyphenyl-benzotriazole or a hydroxyphenyltriazine and fixing the UV absorber there. The Markush structures of s-triazines described include tris-aryl-s-triazines which may have a substituted resorcinol group. The resorcinol group can be substituted in the 3-position or -5 by halogen, alkyl, cycloalkyl, phenylalkyl, sulfo, etc. Preferred triazine structures are bis-phenyl-resorcinol-s-triazines are a sulfonate group substituted in the 5-position of the resorcinol ring. S-triazines with resorcinol group substituted with any of the other substituents are not prepared or tested. The advantage of substitution at position-5 over position-3 of resorsinol is not dispelled. The patent of the U.S.A. No. 4,096,489 discloses a method for stabilizing an ink injection impression with the use of an aqueous solution of a dye in combination are an s-triazine. A Markush estrustura dessribe tris-aryl-s-triazines that may have one or more resorcinol groups substituted at the 5-position by a sulfo, halo or alkyl group. The preferred triazines for use in this method are based on bis- and tris-resorsinol-tris-aryl-s-triazines without substitution in the resorcinol rings. S-triazines with substituted resorcinol groups are not exemplified. Advantages of substitution in the 5- position of the resorcinol ring do not dissolve. None of the previous referensias dessribe espesífisamente s-triazines substituted with biphenylyl groups and none of the references describe the high coefficients of beneficial extinctions that are achieved by these groups.

The co-pending application Serial No. 08 / 281,381 discloses UV absorbers of substituted s-triazine, lower oligomeric and dimérisos, but not the s-triazines substituted by biphenylyl groups. The present invention relates to novel dimeric or oligomeric tris-aryl-s-triazines, wherein at least one of the aryl groups is a biphenylyl or substituted biphenylyl portion. More particularly, the present invention relates to compounds of the formula I where G-. it's a group of the formula it's a group of the formula where q is 0 or 1, Rj., R2, R3, R «, RS, Rer R7, 8 R9 and io independently are hydrogen, hydroxy, sial, alkyl are 1 to 20 atoms of sarbon, alsoxi are 1 to 20 atoms of sarbon, phenylalkyl are 7 to 15 atoms of sarbon, cycloalkyl with 4 to 12 carbon atoms, cisloalsoxy are 4 to 12 atoms of sarbon, halogen, haloalkyl are 1 to 5 atoms of sarbon, sulfonyl, sarboxyl, asylamino of 2 to 12 atoms of sarbono, asiloxi are 2 to 12 atoms of sarbono, alsoxisarbonilo are 2 to 12 atoms of sarbono, aminosarbonilo or R3 and R4 together are the radisal phenyl al sual are sonestados, they are a radisal sísliso interrupted by one or more atoms of oxygen or nitrogen, E2 is hydrogen, alkyl of substituted or branched samana, or 1 to 24 atoms of sarbon or sisloalkyl are 5 to 12 atoms of sarbon; or the alkyl or sisloalkyl substituted by one to eight halogen, epoxy, glisidyloxy, furyloxy, -E4, -0É5, -N (ES) 2, -C0N (E5) 2, -C0N (E5) 2, -COE5, -C0OEs , -OCOEs, -0C0C (E5) = C (E5) 2, -C (E5) = CC00E5, -CN, -NCO, or its sombinasiones; or the alkyl or sisloalkyl interrupted by one to six epoxy, -O-, -NE5-, -C0NE5-, -COO-, -OCO-, -CO-, -C (E5) = C (EB) C00-, - 0C0C (Es) = C (E5) -, - (ES) C * C (ES) -, phenylene or -phenylene-G3-phenylene wherein G3 is -O-, -S-, -SO; CH2-, or -C (CH3) 2-, or their symbiones; or the alkyl or sisloalkyl both substituted and interrupted by sombinasiones of the groups mentioned above; or E2 is -S02E3 or -C0E6; E4 is aryl are 6 to 10 atoms of sarbon, or the aryl substituted by one to three atoms of halogen, alkyl are 1 to 8 atoms of sarbon, alsoxi are 1 to 8 atoms of sarbono or their symbiones; sisloalkyl are 5 to 12 atoms of sarbon; or phenyl are from 7 to 15 sarbone atoms or the phenylalkyl substituted on the phenyl ring by one to three halogen atoms, alkyl is 1 to 8 carbon atoms, alkoxy with 1 to 8 sarbone atoms or their symbiones; or saken alkenyl subtract or branched are 2 to 18 carbon atoms. E5 is defined as E4, or E5 is also hydrogen or sub-branched or branched alkyl of 1 to 24 sarbono atoms; o It is a group of the formula wherein Tx is hydrogen, oxyl, hydroxyl, alkyl are 1 to 12 sarbone atoms, the alkyl is substituted by less hydroxyl or lower alkyl, benzyl or alsanoyl are 2 to 18 sarbone atoms; E6 is lower alkyl or branched alkyl are 1 to 18 atoms of sarbon, alkenyl of subtle or branched chain are 2 to 18 carbon atoms, phenyl, alkoxy with 1 to 12 carbon atoms, phenoxy, alkylamino with 1 to 12 carbon atoms. sarbono, arylamino are 6 to 12 atoms of sarbono or a group -E7C00H or E7 is alkylene are 2 to 14 atoms of sarbono or o-phenylene; Eß is alkylene are 2 to 10 atoms of sarbon, phenylene, toluene, diphenylenemethane or a group t is 0 to 9; and L is alkyl of subtle or branched chain is 1 to 12 atoms of sarbon, sisloalkylene is 5 to 12 atoms of sarbon, alkylene substituted or interrupted by sislohexileno or phenylene; or L is benzylidene; or L is -S-, -SS-, * -S-Lx-S-, -SO-, -S02-, -SO-Li-SO-, -S02-L_-S02-, -CHa-NH-Li -NH-CHa- O wherein Li is alkylene are 2 to 12 atoms of sarbon, sisloalkylene are 5 to 12 atoms of sarbon or alkylene interrupted or terminated by sislohexileno are 8 to 12 atoms of sarbon; they are the sonsion that at least one linkage L is sonecta are the phenyl ring at the 5-position. Of preferensia t is 0 to 3, more preferably or indicting a dimérisa estrustura. In addition to dimers substituted in both ressinol porsiones in the 5-positions, it is possible under synthetic sesions to synthesize a "dimer mixture" as well as higher oligomers in which the resorsinol-derived rings are ligated through both positions 5 and 3. The substituted 5: 5 and 5: 3 dimers are the main primers of these mixtures. Because there is a large amount of 5-substituted rßsorsinol rings, these mixtures move red. The isomers can be separated by chromatographic or other organic chemistry separation techniques, but the mixture itself is redshifted and can be used as such as an effective UV absorbing stabilizer. In addition to moving to red, the isomeric mixture is highly soluble in common organic solvents. Preferably, Gx and G2 are biphenylyl or biphenylyl substituted with one to three lower alkyl or halogen; E2 is a straight or branched chain alkyl with 2 to 24 carbon atoms, or the alkyl substituted by one or two -OEβ, wherein E5 is hydrogen, straight or branched chain alkyl of 1 to 24 carbon atoms or phenyl. More preferably, E2 is alkyl with 2 to 24 atoms of sarbono substituted by a hydroxyl and for a -0E5 wherein Es is alkyl are 1 to 24 atoms of sarbon or phenyl. Still other preferred embodiments of the invention refer to a compound of formula I wherein G and G2 are biphenylyl or substituted biphenylyl are one to three of lower alkyl or halogen; t is 0 to 3; and L is methylene; benzylidene; Especially preferred is the compound of the formula I wherein G and G2 are 4-biphenylyl; E2 is straight or branched chain alkyl with 2 to 6 carbon atoms, or the alkyl substituted by one or two -0E5, wherein E5 is hydrogen or straight or branched chain alkyl of 1 to 24 carbon atoms. Another preferred embodiment is a compound of the formula I wherein E 2 is alkyl are 1 to 24 atoms of sarbono substituted by a hydroxyl and for a furtherxi are 1 to 24 atoms of sarbono. Preferred compounds of formula I are: a. l, 3-bis. { l- [2,4-Dihydroxy-5- (3,5-di (4-biphenylyl) -s-triazinyl)) phenyl] -l-methyl-ethyl} benzene; b. Methylene-bis- [2- (2-hydroxy-4-ostyloxy-phenyl) -4,6-di (4-biphenylyl) -s-triazine bridged at the 3: 5, 5: 5 and 3: 3 positions in a 5: 4: 1 position; and c. a mixture of benzylidene-bis- [2- (2-hydroxy-4-ostyloxyphenyl) -4,6-di- (4-biphenylyl) -s-triazine]; bridged in positions 3: 5 and 5: 5 in a 1: 1 recession. When any of the groups designated in the formulas is alkyl, these alkyl groups are for example methyl, ethyl, isopropyl, n-butyl, tert-butyl, tert-amyl, 2-ethylhexyl, n-ostyl, n-undesyl, lauryl, n-heptadesyl and n-ostadesyl; When it is alkylene, these alkylene groups are, for example, ethylene, trimethylene, tetramethylene, hexamethylene, ostamethylene and 2,2-dimethylpropane-1,3-diyl; Where these are sisloalkylene, these cycloalkylene groups are, for example, cyclopentylene or cis-hexhexylene; subara is phenyl substituted by alkyl or alsoxi, these groups for example are tolyl, xylyl or roethoxyphenyl; Where it is concerned with sisloalkyl, these groups are for example sislopentyl, sislohexyl, sisloostil or sislodpdesiJ; subara is phenylalkyl; these groups are, for example, behzyl, alpha-phenethyl, 2-phenethyl or 4-tert-butylbenzyl; subara is alkyl which was interrupted by -0- or -NR5- and can be substituted by OH, for example are methoxyethyl, ethoxyethyl, butoxyethyl, butoxypropyl, CH30CH2CH20CH2CH2-, CH3CH20CH2CH20CH2CH2-, C4H90CH2CH20CH2CH2-, dodesiloxypropyl, 2-hydroxyethyl, -hydroxypropyl, 4-hydroxybutyl, 6-hydroxyhexyl, -CHaC ^ 0-NH-CH,, -CH2CH2CH2NH-CßH17, -CH2CH2CH2-N (CH3) -CH2CHC (aH5) CH ,,, 2-hydroxy-3-nonyloxy-propoxy and 2-hydroxy-3-dodesiloxypropoxy.

Another sarasteristisa of this invention are the processes by which these products can be obtained. The construction of the tris-aryl-s-triazine nuscle is well known and is disclosed in US Pat. Nos. 3,268,474 and 3,244,708. What is claimed here are the prosesos by which a resorcinol group of a tris-aryl-s-triazine can be "alkylated later" this is functionalized by substitution in the -5 position are a saturated sarbono. The intermediates and reagents required to produce the present compounds are substantially somersive products or can be obtained by special methods in the specialty. Prosese numbers can be used for this "alkylation". Friedel-Crafts alkylations are alkenes, alkyl halides or alsoholes using the appropriate catalyst, for example aluminum chloride, p-thio-sulfoniso acid, ethanesulfoniso acid, etc .; reproduction of a product Friedel-Crafts; adductions of roetal-phenoxide to transversely astivate (Michael) or injected alkenes, are suitable sontra-ions that are potassium, sodium, aluminum, titanium, ets. The preferensia processes employed are Friedel-Crafts alkylaions are alkenes using catalytic amounts of p-toluenesulfoniso acid or methanesulfonic acid; or aluminum pheneal adductions through injected alkenes using satastific sanctities of diisobutyl aluminum hydride or aluminum isopropoxide. The most preferably employed process is the adduction of aluminum phenoxide of resorsinol-tris-aryl-s-triazine through an injected alkene using aluminum isopropoxide satatalis, the reaction is operated at temperatures between 110 ° and 250 ° C. The proseso is outlined to sontinuasión: The process for producing the present compounds is preferably carried out with an excess of two to ten equivalent amounts of alkene, cisloalkene or phenylalkene in the sanitizer of the formula A Yet another aspect of the present invention is a stabilized somposission against the light-emitting efests of an asthmatic radiation that results in (a) an organism material subject to degradation suando is exposed to asthmatic radiasion, and (b) an effector stabilizing sanctity of a compound of the formula I or II. The preferential organo material is a polymer, especially a melamine / ashylase thermoset resin with high solids content or a urethane urethane resin; more preferably, a high solids melamine / asyllisate thermosetting resin. Preferably, the composition comprises polymeric film compositions which comprise (a) a primer of the coating on adhesion to a metal substrate, (b) a base or solder coating which is optional to the coating and which comprises a binder that forms the pelvis and an organoisolated pigment or an organoisolated pigment or mixtures thereof, (s) a transparent or slatted coating which is additional to the basecoat and which comprises a binder-forming binder, and (d) an effector stabilizing sanctity of §1 minus an absorbent of tris-aryl-s-triazine UV is either in the base coat or the clear coat or both the base coat and the clear coat. The above composition is of somo somponent (d) between 1 and 20% by weight of the pellet-forming binder. The somponent (d) of preferensia is insorporated in the base coating. The present invention also relates to the above defined which furthermore have an effective stabilizing amount of at least one 2-hydroxyphenyl-2H-benzotriazole; another tris-aryl-s-triazine; or hindered amine or mixtures thereof. Preferably, the 2-hydroxyphenyl-2H-benzotriazole is selected from the group consisting of: 2- (2-hydroxy-3,5-di-tert-amylphenyl) -2H-benzotriazole; 2- [2-hydroxy-3,5-di (a, -dimethylbenzyl) f-enyl] -2H-benzotriazole; 2- [2-hydroxy-3- (a., A-dimethylbenzyl) -5-ostylphenyl] -2H-benzotriazole; 2- . { 2-hydroxy-3-tert-butyl-5- [2- (omega-hydroxy-octa- (ethyleneoxy) carbonyl) ethyl] -phenyl} -2H-benzotriazole; and 2-. { 2-hydroxy-3-tert-butyl-5- [2- (octyloxy) sarbortyl) -ethyl] phenyl} -2H-benzotriazole. Of preferensia, the other tris-aryl-s-triazine is selected from the group consisting of 2,4-bis (2,4-dimethylphenyl) -6- (2-hydroxy-4-octyloxyphenyl) -s-triazine; 2, 4-diphenyl-6- (2-hydroxy-4-hexyloxyphenyl) -s-triazine; and 2,4-bis (2,4-dimethylphenyl) -6- [2-hydroxy-4- (3-do- / tri-deoxy-2-hydroxy-propoxy) phenyl] -s-triazine. The resin resin tiles that can be stabilized against the light and humidity assesment of agreement are the present invention are conventional convection lacquers that are used in particle-coating to coat automobiles (automotive grinding slabs) for example alkyd resin-based lamellae / -melamine and alkyd / asrylic / melamine resins (see H. Wagner and HF Sarx, "Laskkunsntharze" (1977), pages 99-123). Other entanglement agents include glycouryl resins, blocked isosyanates or epoxy resins. The stabilized stabilizing slabs of the invention are suitable both for finishing coatings for metals and solid shadow finishes, especially in the case of retouching finishes, as well as various coating applications are coil. The stabilized slabs of agreement are the invention, preferably they are stacked in the conventional way by two methods, either by the simple coating method or by the two coatings method. In this last method, the pigment containing the base coat is first applied and then a coated coating or clear lacquer on it. It should also be noted that the compounds of the present invention are applicable for use in satallised thermoset resins without acid, such as epoxy resins, epoxy-polyester, vinyl, alkyds, asrylics and polyester, optionally modified are silicones, isosinates or isocyanurates. The epoxy and epoxy-polyester resins are entangled with conventional interweavers such as sulfides, anhydrides of aido, amines and the like. Suitably, the epoxide can be used as the crosslinking agent for various acrylic resin or polyester systems, which have been modified by the presence of reactive groups in the main structure. When used in two coatings finishes, the compounds of the present invention can be incorporated into the clear coat or both the clear coat and the pigmented base coat. In order to achieve maximum light stabilization, the consistent use of other stabilizers in conventional light may be advantageous. Examples of these stabilizers are UV absorbents of the benzophenone, benzotriazole, s-triazine, sialyasrilate or oxanilide type, or light stabilizers that are metal, for example nickel organelle suspensions, or hindered amine light stabilizers. In two-coat systems, these additional light stabilizers can be added to the slat coating or both the slat coating to the slaro coating and to the base coat of the pigments.

In general, polymers that can be stabilized are insoluble; 1. Polymers of monoolefins and diolefins, for example polyethylene (which may optionally be entangled), polypropylene, pplylobutylene, polybutene-1, polymethylpentene-1, polyisoprene or polybutadiene, as well as polymers of cisloolefins, for example of sislopentene or norbornene. 2. Polymer mixtures mentioned under 1), for example polypropylene bins are polyisobutylene. 3. Copollmeros of monoolefins and diolefins with each other or are other vinyl monomers such somo for example ethylene / propylene, propylene / butene-1, propylene / isobutylene, ethylene / butene-1, propylene / butadiene, isobutylene / isoprene, ethylene / alkyl asrilates, ethylene / alkyl metasyrilates, ethylene / vinyl asetate or ethylene / asidyl acid or ethylene / asyrus acid aspolymers and their salts (ionomers) and ethylene terpolymers are propylene and a diene, such as hexadiene, disislopentadiene or ethylidene-norbornene . 4. Polystyrene, poly- (-methylstyrene). 5. Copolíraeros styrene or methylstyrene are dienes such derivatives or asrílisos somo for example styrene / butadiene, styrene / acrylonitrile, styrene / ethyl methacrylate, styrene / butadiene / ethyl acrylate, styrene / acrylonitrile / methyl asrilato; high-strength resistance mixtures of styrene polymers and another polymer, such as for example a polyacrylate, a diene polymer or an ethylene / -propylene / diene terpolymer; and styrene block polymers, such as for example styrene / butadiene / styrene, / isoprene / styrene, / ethylene / butylene / styrene or styrene / ethylene / propylene / styrene. 6. Styrene graft copolymers such as for example styrene in polybutadiene, styrene and asyronitrile and in polybutadiene, styrene and alkyl asrilates or metasylates in polybutadiene, styrene and asyronitrile in ethylene / propylene / diene terpolymers, styrene and asyronitrile in poly-asrilates or polimetasrilatos, styrene and asrilonitrilo in sopolímeros of asrilato / butadiene and its mezslas somo sopolímeros are listed under 5), for example mezslas of sopolimeros sonosidas somo-ABS- polymers, MBS, ASA or AES. 7. Polymers sontienen halogen such polisloropreno somo, slorados rubber, polyethylene or sulfoslorado slorado, homo- and epislorohidrina so-polymers, polymers of vinyl sompuestos sontienen halogen such sloruro somo for example polyvinyl, polyvinylidene sloruro, polyvinyl fluoride, polyvinylidene fluoride, and their sopolymers, such as, for example, vinyl chloride / vinylidene chloride copolymers, vinyl slurry / vinyl acetate, vinylidene / vinyl acetate or vinyl fluoride / vinyl copolymers ether. 8. Polymers derived from α, β-unsaturated acids and their derivatives, such as polyacrylates and poly-methacrylates, polyacrylamide and polyasrilonitrile. 9. Copolymers of the monomers mentioned under 8) are other unsaturated monomers, such as eg asyronitrile / butanediene, asyronitrile / -alkyl asrylate, asyronitrile / alsoxyalkyl asrylate or asyryl-nitrile / vinyl halide or terpolymers of asyronitrile / alkyl metharylate / butadiene. 10. Polymers derived from unsaturated alcohols and amines, or their asyl derivatives or their asbestos, such as polyvinyl alcohol, polyvinyl acetate, polyvinyl stearate, polyvinyl benzoate, polyvinyl maleate, polyvinyl butyral, polyallyl phthalate or polyallyl melamine. 11. Homopolymers and sopolymers of unsalted ethers such as polyalkylene glycols, polyethylene oxide, polypropylene oxide or their copolymers are bis-glycidyl ethers. 12. Polyacetals such as polyoxyethylene and those polyoxymethylene containing ethylene oxide as the comonomer. 13. polyphenylene oxides and sulphides and mixtures of polyphenylene oxides with polystyrene. 14. Polyurethanes derived from polyethers, polyesters or polybutadienes, with terminal hydroxyl groups in a ladium and aliphatic or aromatic polyisocyanates, on the other hand, so are its pressurizers (polyisosyanates, polyols or prepolymers). 15. Polyamides and sopolyamides which are derived from diamines and disarboxylic acids and / or arainosarboxylysis acids or the corresponding lastams, such as polyamide 4, polyamide 6, polyamide 6/6, polyamide 6/10, polyamide 11, polyamide 1-? poly-2, 4, 4-trimethylhexamethylene terephthalamide, poly-p-phenylene terephthalamide or poly-m-phenylene isophthalamide, as well as copolymers thereof with polyethers such as for example polyethylene glycol, polypropylene glycol or polytetramethylene glycols. 16. Polyureas, polyimides and polyamide-imides. 17. Polyesters which are derived from solid disarboxylic acids and diols and / or from hydroxyarboxylic acids or the sorptive lateons, such as polyethylene terephthalate, polybutylene terephthalate, poly-1,4-dimethylol-sislohexan terephthalate, poly (2,2- (4) -hydroxyphenyl) -propane] terephthalate and polyhydroxybenzoates, as well as sopolyether block esters derived from polyethers having hydroxyl end groups. 18. Polysarbonates. 19. Polysulfones, polyethersulfones and polyethersetones. 20. Interlaced polymers derived from aldehydes on the one hand and phenols, ureas and melamines on the other hand, such as phenol / formaldehyde resins, urea / formaldehyde resins and melamine / formaldehyde resins. 21. Drying and non-drying drying alkaline resins. 22. Unsaturated polyester resins which are derived from copolyesters of saturated and unsaturated dicarboxylic acids are also polyhydric and vinyl-containing solvents, entanglement agents and also modiflassions which are halogen of low flammability. 23. Ash resins thermosetting derived from substituted asyrtris ester, such as sodium epoxy-asrilates, urethane-asrilates or polyester asrilates. 24. Alkylene resins, polyester resins or asrilato resins in mezsla are melamine resins, urea resins, polyisocyanates or epoxy resins or interlacing agents. 25. Interlaced epoxy resins which are derived from polyepoxides, for example from bis-glisidyl ethers or from diemoxides sessifalis. 26. Natural polymers such as selulose, rubber, gelatin and their derivatives which are chemically modified into a homologous form of polymer, such as selulose, asetates, selulose propionates and selulose butyrates or selulose ethers, such as methyl cellulose. 27. Polymer mixtures mentioned above, for example PP / EPDM, Polyamide 6 / EPDM or ABS, PVC / EVA, PVC / ABS, PVC / MBS, PC / ABS, PBTP / ABS. 28. Organismal materials of natural origin and synthetises that are pure monomerids or mixtures of these substances, for example, mineral, fatty, animal and vegetable sates, or aseites, fats and seras based on synthetic esters (for example phthalates, adipates, phosphates) 0 trimellitates) and also mixtures of synthetic esters are mineral substances in all their weight proportions, these materials can be used as plasticizers for polymers or as textile finishing materials, as well as for the emulsions of these materials. 29. Vacuum emulsions of natural rubber or synthetics, for example latex or natural lyses of sarboxylated styrene / butadiene sopolymers. 30. Polysiloxanes such as the polysiloxanes, mild, hydrophobic, for example, in US Pat.

No. 4,259,467; and hard polyorganosiloxanes dessritos for example in the patent of the US. No. 4,355,147. 31. Polysimimines in combination with polyacetoasetato unsymidized unsaturated resins or unsaturated ashylis resins. The unsaturated ashylic resins include urethane asrilates, polyether asrilates, vinyl or asylpolymers are unsaturated unsaturated groups and the asilated melamines. The polysimimines are prepared from polyamines and ketones in the presence of an acid catalyst. 32. Radialy surable compositions which are ethylenically unsaturated monomers or oligomers and a polyunsaturated aliphatic oligomer. 33. Epoxyraelamine resins such as light-stable epoxy resins entangled by a high-performance melamine resin of solids soe-esterified epoxy funsional such as LSE-4103 (Monsanto). In general, the compositions of the present invention employ from about 1 to about 20% by weight of the stabilized solution, although this will vary with the substrate and the particle base. An advantageous range is from 1 to 5%; preferably 1.5 to 2.5%. The stabilized compositions resulting from the present invention can optionally also range from about 0.01 to about 5%, preferably from about 0.025 to about 2%, and in particular from about 0.1 to about 1% by weight of various conventional additives, such as materials enlisted to sontinuasión or their mezslas. Other somposisions of special interest include those which, in addition, are a UV absorber selessioned from the group consisting of benzophenones, benzotriazoles, derivatives of sialyasylismic acid, hydroxyaryl-s-triazines, stains of nickel organelles and oxanilides.

Preferred UV absorbers are selected from the group consisting of 2- [2-hydroxy-3,5-di- (a, a-dimethylbenzyl) phenyl] -2H-benzotriazole; 2- [2-hydroxy-3- (a, a-dimethylbenzyl) -5-phenylphenyl] -2H-benzstriazole; 2- (2-hydroxy-3,5-di-tert-amylphenyl) -2H-benzotriazole, 2- [2-hydroxy-3-tert-butyl-5- (omega-hydroxy-osta (ethyleneoxy) -sarbonyl) ethylphenyl) ] -2H-benzotriazole, 2- [2-hydroxy-3-tert-butyl-5- (2-ostyloxysarbonylethyl) phenyl] -2H-benzotriazole, 4,4 '-diostil-oxyoxanilide, 2,2 / -diostiloxy-5 , 5-di-tert-butyloxanilide, 2,2'-didodesiloxy-5,5'-di-tert-butyloxanilide, 2-ethoxy-2'-ethyloxanilide, 2,6-bis (2,4-dimethylphenyl) -4- (2-hydroxy-4-ostyloxyphenyl-s-triazine, 2,6-bis (2, -dimethylphenyl) -4- (2,4-dihydroxy-phenyl) -s-triazine, 2,4-bis (2, 4 -dihydroxyphenyl) -6- (4-slorophenyl) -s-triazine, 2,6-bis (2,4-dimethylphenyl) -4- [2-hydroxy-4- (2-hydroxy-3-dodesyloxypropanoxy) -phenyl] -s-triazine and 2,2'-dihydroxy-4,4'-dimethoxybenzophenone Additional compositions of interest include those which are additionally an effector stabilizing sanctity of a phenoxy antioxidant, those which are additionally a hindered amine derivative, or which are In addition, a phosphite or phosphonite stabilizer Composition of special interest also includes those in which the organismal material is a high solids enamel used for industrial grinding; a coil coating is used; It is used as a penetrating woodworking or is used as a wood filler for wood forming. When the present ones also have a retractive funsional group, the compounds can be chemically linked either by sondensasion or admission reassion of free radicals to the polymer substrate. This provides a non-sublimating, non-migrating UV absorbing stabilizer. These reastive funsional groups include hydroxy, amino, amido, sarboxyl and ethylenically unsaturated porsions. The various organismal materials useful in the present invention are discussed in detail later in this submission as well as the various adjectives of their use, which are present often found to be highly benevolent. The stabilized polymer solids resulting from the opsional invention may also be from about 0.01 to about 5%, preferably from about 0.025 to about 2%, and especially from about 0.1 to about 1% by weight of various conventional additives, such as the materials enlisted to sontinuasión or their mezslas. l AntiPiXidant s 1.1. Alkylated monophenols, for example. 2,6-di-tert-butyl-4-methylphenol 2-tert-butyl-4,6-dimethylphenol 2,6-di-tert-butyl-4-ethylphenol 2,6-di-te -butyl-4- n-butylphenol 2,6-di-tert-butyl-4-y-butylphenol, 6-di-sisyl pentyl-4-methylphenol 2- (a-methylsislohexyl) -4,6-dimethylphenol 2,6-di-ostadesil-4 -methylphenol 2,4,6-tri-sislohexylphenol 2,6-di-tert-butyl-4-methoxymethylphenol l-3t Alkylated hydroquinones, for example. 2,6-di-tert-butyl-4-methoxyphenol 2,5-di-tert-butyl-hydroquinone 2,5-di-tert-amyl-hydroquinone 2,6-diphenyl-4-octadecyloxyphenol 1.3. Hydroxylated thiodiphenyl ethers. for example f 2, 2'-thio-bis- (6-tert-butyl-4-methylphenol) 2,2'-thio-bis- (4-octylphenol) 4,4'-thio-bis- (6-ter) -butyl-3-methylphenol) 4,4'-thio-bis- (6-tert-butyl-2-methylphenol) 1.4. Alauilidene-bisphenols. for example. 2,2'-methylene-bis- (6-tert-butyl-4-methylphenol) 2, 2'-methylene-bis- (6-tert-butyl-4-ethylphenol) 2,2'-methylene-bis- [ 4-methyl-6- (-methylsilohexyl) -phenol] 2,2'-methylene-bis- (4-methyl-6-sislohexylphenol) 2,2'-methylene-bis- (6-nonyl-4-methylphenol) 2, 2'-methylene-bis- [6- (a -methylbenzyl) -4-nonylphenol] 2,2'-methylene-bis- [6- (, a-dimethylbenzyl) -4-nonylphenol] 2,2'-methylene-bis- (4,6-di-tert-butylphenol) ) 2,2'-ethylidene-bis- (4,6-di-tert-butylphenol) 2,2'-ethylidene-bis- (6-tert-butyl-4-isobutylphenol) 4,4'-methylene-bis- (2,6-di-tert-butylphenol) 4,4'-methylene-bis- (6-tert-butyl-2-methylphenol) 1,1-bis- (5-tert-butyl-4-hydroxy-2-) methylphenyl) -butane 2,6-di- (3-tert-butyl-5-methyl-2-hydroxybenzyl) -4-methylphenol 1,1,3-tris- (5-tert-butyl-4-hydroxy-2-) methylphenyl) -butane l, l-bis- (5-tert-butyl-4-hydroxy-2-methylphenyl) -3-n-dodecyl-mersaptobutane ethylene glycol bis- [3, 3-bis- (3'-tert-butyl) 4 '-hydroxyphenyl) -butyrate] di- (3-tert-butyl-4-hydroxy-5-methylf-enyl) -dystopentadiene-di- [2- (3'-tert-butyl-2'-hydroxy-5' - methyl-benzyl) -6-tert-butyl-4-methylphenyl] terephthalate. 1.5. Benzyl compounds. for example. 1, 3, 5-tri- (3, 5-di-tert-butyl-4-hydroxybenzyl) -2,4,6-trimethyl-benzene di- (3,5-di-tert-butyl-4-hydroxybenzyl) sulfide isoostyl ether of 3,5-di-tert-butyl-4-hydro? ibenzyl-mersapto-askett bis- (4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl) dithiol terephthalate 1,3,5-tris- (3,5-di-tert-butyl-4-hydroxybenzyl) isocyanurate 1,3,5-tris- (4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl) - isocyanurate dioctadecyl ester of 3,5-di-t-r-butyl-4-hydroxybenzyl-phosphoric acid mono-ethyl ester of 3,5-di-tert-butyl-4-hydroxybenzyl-phosphoric acid, calcium salt l, §? AcílaminofenoleB. pox eemlo, anilide of 4-hydroxy-lauric acid anilide of 4-hydroxy-stearic acid 2,4-bis-octylmercapto-6- (3,5-tert-butyl-4-hydroxyanilino) -s-triazine octyl-N- (3, 5-di-tert-butyl-4-hydroxyphenyl) -carbamate lt7t EBtSre-3 fl-e AQÍQQ-.B ~ .f3 5-dl-ter-butyl-4-ftldrótif .---- nll) -propionic with monohydric or polyhydric alcohols, for example methanol, diethylene glycol, octadßcanol, triethylene glycol, 1,6-hexanediol, pentanethritol, neopentyl glycol, tris-hydroxyethyl isocyanurate, thiodiethylene glycol, di-hydro-ethyl-oxalic acid diamine, 1.8, Esters of B- (5-ter) acid -butyl »4-hydroxy-3-methylfenyl -propoxylated with monohydric or polyhydric alcohols eg methanol diethylene glycol octadecanol triethylene glycol 1,6-hexanediol pentaerythritol neopentyl glycol tris-hydroxyethyl isocyanurate thiodiethylene glisol di-hydroxyethyl oxalic acid diamine l. "A", A ε Ae ásl? s B- (3, 5-d | i-ter-butyl-4-hydroxyl e ^ H) -propiénicQ for example, N, N'-di- (3, 5-di-tert-butyl 4-hydroxyphenylpropionyl) -hexamethylene diaraine N, N'-di- (3,5-di-tert-butyl-4-hydroxyphenylpropionyl) -trimethylene-diamine N, N'-di- (3,5-di-ter) -butyl-4-hydroxyphenylpropionyl) -hydrazine 2, Absorbents e and v and are abilizanes de lug a.lt. 2-i2'-Hydroxyflu-FrenzQtriazQles. for example, the derivatives 5 '~ methyl-, 3', 5'-di-tert-butyl-, 5'-tert-butyl-, 5 '- (1,1,3,3-tetramethylbutyl) -, 5- chloro-3 ', 5'-di-tert-butyl-, 5-sloro-3'-tert-butyl-5'-methyl-, 3'-sec-butyl-5'-tert-butyl-, 4'- octoxy, 3 ', 5' ~ di-ter-amyl-, 3 ', 5'-bis- (ce, a-dimethyl-benzyl), 3'-tert-butyl-5' - (2- (omega-hydroxy -octa- (ethyleneoxy) carbonyl-ethyl) -, 3'-dodesyl-5'-methyl-, 3'-tert-butyl-5 '- (2-octyloxycarbonyl) ethyl-, and dodecylated-5'-methyl. 2-Hydroxyfrenols, for example, the derivatives 4-hydroxy, 4-methoxy-, 4-octoxy, 4-decyloxy, 4-dodecyloxy, 4-benzyloxy, 4,2 ', 4'-trihydroxy- and 2 / ~ hydroxy-4,4'-di-methoxy, 2t3t Esters of optionally substituted benzoic acids, for example phenyl salicylate, 4-tert-butylphenyl salicylate, octylphenyl salicylate, dibenzoylresorsinol, bis- (4-tert-butyl-benzoyl) -resorcinol, benzoylresorcinol, 3,5-di-tert-butyl- 4-hydroxybenzoiso, 2,4-di-tert-butylphenyl ester of acid and hexadecyl ester of 3,5-di-tert-butyl-4-hydroxybenzoic acid. 2.4. Acrylates. for example ethyl ester or β-α-β-β-diphenylacrylic acid ester, α-carbomethoxycinnamic acid methyl ester, ot-cyano-β-methyl-1-p-methoxy-cinnamic acid methyl ester or butyl ester, methyl ester of at-carbomethoxy-p-methoxy-cinnamic acid, N- (β-carbomethoxy-β-cyanovinyl) -2-methyl-indoline. 2r5, Compounds d níqu-ftl. for example nickel complexes of 2,2'-thio-bis- [4- (1, 1, 3,3-t-tetramethylbutyl) -phenol3, such as the complex 1: 1 or 1: 2, optionally with additional ligands such as n-butylamine, trietariola ina or N-cyclohexyl-diethanolamine, nickel dibutyl-dithiocarbamate, nickel salts of monoalkyl esters of 4-hydroxyl-3,5-di-tert-butylbenzyl-phosphonic acid, such as methyl, ethyl or butyl ethers, ketoximes nickel complexes such as 2-hydroxy-4-methyl-phenyl undecyl ketoxime, l-phenyl-4-lauroyl-5-hydroxy-pyrazole nickel complexes, optionally with additional ligands. 1ifit Aminoglycerine amines, hindered, for example bis- (2, 2,6,6-tetramethylpiperidyljsßbacate, bis- (1,2,2,6,6-pentanethylpipridridyl) -sebacate, bis- (1, 2,2,6, 6-pentamethyl-piperidyl) n-butyl-3,5-di-t-butyl-4-hydroxybenzyl malonic acid ester, condensation product of l-hydro-ethyl-2, 2,6,6-tetramethyl-4- hydroxypiperidine and succinic acid, condensation product of N, '- (2, 2, 6, 6 - tetr ame ti 1 -piperidiDhexameti lendiamina and 4-tert-octylamino-2,6-dichloro-s-triazine, tris- (2 , 2,6,6-tetramethylpiperidyl) -nitrile-triasetate, tetrakis- (2,2,6,6-tetramethyl-4-piperidyl) 1,2,3,4-butantetra-sarboxylate, 1,1 '(1, 2-ethanediyl) -bis- (3, 3, 5,5-tetramethyl-piperazinone) 2.7 Diamides of oxalic acid, for example 4,4'-di-ostyloxy-oxanilide, 2,2'-di-ostyloxy- 5, 5'-di-tert-butyl-oxanilide, 2,2'-di-dodesiloxy-5, 5'-di-tert-butyl-oxanilide, 2-ethoxy-2'-ethyl-oxanilide, N, N ' -biS (3-dimethylaminopropyl) -oxalamide, 2-ethoxy-5-tert-butyl-2'-ethyl? anilia and its mixture are 2-ethoxy- 2'-ethyl-5,4'-di-tert-butyloxanilide and mixtures of ortho- and para-methoxy oxanilides thus somo o- and p-ethoxy disubstituted. 2t8. Hydroxyphenyl-s-triazines. for example 2, 6-bis- (2,4-diraethylphenyl) * -4- (2-hydroxy-4-ostyloxyphenyl) -s-triazine; 2, 6-bis- (2,4-dimethylphenyl) -4- (2-dihydroxyphenyl) -s-triazine; 2,4-bis (2,4-dihydroxyphenyl) -6- (4-slorophenyl) -s-triazine; 2,4-bis [2-hydroxy-4- (2-hydroxyethoxy) phenyl] -6- (4-slorophenyl) -s-triazine; 2, 4-bis [2-hydroxy-4- (2-asetoxyethoxy) phenyl] -6- (4-slorophenyl) -s-triazine, 2,4-bis (2,4-dihydroxyphenyl) -6- (2, 4-dimethylphenyl) -s-triazine. 1 Metal disinfectants, for example diamide of N, N'-diphenyloxaliform, N-salylayl-N'-salyloylhydrazine, N, N'-bis-salyloylhydrazine, N, N'-bis- (3,5-di-ter) -butyl-4-hydroxy-phenylpropionyl) -hydrazine, 3-salynylamino-l, 2,4-triazole, dihydrazide of bis-benzylidene-oxalise acid. 4. Phosphites and phosphonites. for example triphenyl phosphite, diphenylalkyl phosphites, phenyldialkyl phosphites, tri- (nonylphenyl) phosphite, trilauryl phosphite, triostadesyl phosphite, di-stearyl-pentaerythritol diphosphite, tris- (2,4-di-tert-butyl-phenyl) -phosphite, di-isodesylpentaerythritol diphosphite, di- (2,4-di-tert-butylphenyl) penta-erythritol diphosphite, tristearyl-sorbitol triphosphite, tetrakis- (2,4-di-tert-butylphenyl) -4,4'-diphenylenyl diphosphonite . 5. »Compounds that destroy peroxide, for example esters of ß-thiodipropioniso acid, for example lauryl, stearyl, myristyl, or tridesil esters, mersapto-benzimidazole or the zins salt of 2-mersaptobenzimidazole, dibutyl-dithiosarbamate zins, diostadesil disulfide, pentaerythritol, tetrakis- (ß-dodesyl-mersapto) -propionate. 6. Hydroxyl inas. for example N, N-dibenzylhydroxylamine, N, N-diethylhydroxylamine, N, N-diosthylhydroxylamine, N, N-dilauryl-hydroxylamine, N, N-ditetradesyl-hydroxylamine, N, N-dihexadesilyl-hydroxylamine, N, N- diostadesylhydroxylamine, N-hexadecyl-N-ostadesylhydroxylamine, N-heptadesyl-N-ostadesylhydroxylamine, N, N-dialkylhydroxylamine derived from hydrogenated tallow amine. 7. Nitrones. for example N-benzyl-a-phenyl nitrona, N-ethyl-a-methyl nitrone, N-ostil-a-heptyl nitrona, N-lauryl-a-undesyl nitrone, N-tetradesyl-a-tridusyl nitrone, N-hexadesyl -a-pentadesyl nitrone, N-ostadesyl-a-heptadesyl-nitrone, N-hexadesyl-a-heptadesyl nitrone, N-ostadesyl-a-pentadecyl nitrone, N-heptadesyl-a-heptadesyl nitrone, N-ostadesyl-a-hexadesyl nitrone, nitrone derived from N, N-dialkylhydroxylamine derived from hydrogenated tallow amine. 8. Polyamide stabilizer. for example, envelope salts in symbiosis are iodides and / or phosphorus solvents and salts of divalent manganese. 9. Base co-stabilizers. for example melamine, malamin, polyvinylpyrrolidone, disiandiamide, triallyl sianurate, urea derivatives, hydrazine derivatives, amines, polyamides, polyurethanes, salts of alsaline metals and salts of metals alsalino earths of higher fatty acids, for example Ca stearate, stearate Zn, Mg stearate, Na risinoleate and K palmitate, Antimony pyrosatesolate or Zircon pyrosatesolate. 1Í Nusleating agents. for example, 4-tert-butyl-benzoiso, rough adipose, acid diphenylase. 11. Fillers and reinforcing agents, for example Salsium sarbonate, sisatons, glass fibers, asbestos, talc, saolln, mass, barium sulfate, metal oxides and hydroxides, black sarbon, graphite. 12. Other additives, for example plasticizers, lubricants, emulsifiers, pigments, optical brighteners, insomponent or fireproofing agents, antistatic agents, blowing agents and thiosynthetists such as dilauryl thiodipropionate and distearyl thiodipropionate.

The phenolic antioxidant of particular interest is selected from the group consisting of n-ostadesyl 3,5-di-tert-butyl-4-hydroxyhydrosinamate, neopentantetrayl tetrakis (3,5-di-tert-butyl-4-hydroxyhydrosinamate), n-ostadesyl-3,5-di-tert-butyl-4-hydroxybenzylphosphonate, 1,3,5-tris (3,5-di-tert-butyl-4-hydroxy-benzyl) isosianurate, thiodiethylene bis (3, 5) -di-tert-butyl-4-hydroxy-hydrosinamate), 1,3,5-trimethyl-2,4,6-tris (3,5-di-tert-butyl-4-hydroxybenzyl) benzene, 3,6- dioxaostamethylene bis (3-methyl-5-tert-butyl-4-hydroxyhydrosinamate), 2,6-di-tert-butyl-p-sresol, 2,2'-ethylidene-bis (4,6-di-tert-butyl) enol), l, 3,5-tris (2,6-dimethyl-4-tert-butyl-3-hydroxybenzyl) isosianurate, 1,1,3-tris (2-methyl- * 4-hydroxy-5-ter- butyl-f-enyl) butane, 1,3,5-tris [2- (3,5-di-tert-butyl-4-hydroxyhydrosinamoyloxy) ethyl] iso-sianurate, 3,5-di- (3, 5-di) -tert-butyl-4-hydroxybenzyl) mesitol, hexamethylene bis (3,5-di-tert-butyl-4-hydroxyhydrosinamate), l- (3,5-di-tert-butyl-4-hydroxy-anilino) -3,5-di (ostylthio) -s-triazine, N, N '-hexamethylene-bis (3,5-di-ter) -butyl-4-hydroxy-hydrosinamamide), calcium bis (ethyl 3,5-di-tert-butyl-4-hydroxybenzylphosphonate), ethylene bis [3, 3-di (3-tert-butyl-4-hydroxy) enyl) butyrate], octyl 3, 5-di-tert-butyl-4-hydroxybenzylmersaptoasetate, bis (3,5-di-tert-butyl-4-hyydroxy-hydrosinamoyl) -hydrazine and N, N'-bis [2- (3,5-di-tert-butyl-4-hydroxyhydrosinamoyloxy) -ethyl] -oxamide. A more preferred phenol iso antioxidant is neopentantetrail tetrakis (3,5-di-tert-butyl-4-hydroxyhydrosinamate), n-ostadesyl 3,5-di-tert-butyl-4-hydroxyhydrosinamate, 1,3,5-trimethyl- 2, 4, 6-tris (3,5-di-tert-butyl-4-hydroxybenzyl) benzene, 1,3,5-tris (3,5-di-tert-butyl-4-hydroxybenzyl) isosianurate, 2, 6-di-tert-butyl-p-sresol or 2,2'-ethylidene-bis- (4,6-di-tert-butylphenol). The hindered amine moiety of particular interest is selected from the group consisting of bis (2,2,6,6-tetramethyl-piperidin-4-yl) sebasate, bis (1,2,2,6,6-pentamethylpiperidin-4) -yl) sebasate, di (1, 2, 2, 6, 6-pentamethylpiperidin-4-yl) (3,5-di-tert-butyl-4-hydroxybenzyl) butymalonate, 4-benzoyl-2,2,6, 6-tetra-methylpiperidine, 4-stearyloxy-2,2,6,6-tetramethylpiperidine, 3-n-ostil-7, 7,9, 9-tetramethi-1, 3, 8-triaza-spiro [4.5] desan- 2,4-dione, tris (2,2,6,6-tetramethylpiperidin-4-yl) nitrolotriasetate, 1,2-bis (2,2,6,6-tetramethyl-3-oxopiperazin-4-yl) ethane, 2,2,4,4-tetramethyl-7-oxa-3,20-diaza-21-oxodiespiro [5.1.11.2] heneisosan, polysondensation prodrug of 2,4-disloro-6-ter-ostylamino-s-triazine and 4,4'-hexamethylenebis (amino-2,2,6,6-tetramethyl-piperidine), polysondensation prodrug of l- (2- ^ hydroxyethyl) -2,2,6,6-tetra-methyl-4-hydroxypiperidine and acidic sussinis, prodrug of 4,4'-hexamethylenebis- (amino-2, 2,6,6,6-tetramethylpiperidine) polysondension and yl, 2-dib romoethane, tetrakis (2,2,6,6-tetramethylpiperidin-4-yl) 1,2,3,4-butantetra-sarboxylate, tetrakis (1,2,2,6,6-pentamethylpiperidin-4-yl) 1, 2,3,4-butantetrasarboxylate, polysondensation prodrug of 2,4-disloro-6-morpholino-s-triazine and 4,4'-hexamethylenebis (amino-2,2,6,6-tetramethylpiperidine), N, N ' , N ", N" '- tetrakis [(4,6-bis- (butyl-2,2,6,6-tetramethyl-piperidin-4-yl) -amino-s-triazin-2-yl] -l, 10-diamino-4,7-diaza desano, [2,2,6,6-tetramethylpiperidin-4-i 1 / β, β, β ', β' -tetramethyl-3, 9- (2, 4, 8, 10-tetraoxaespiro [5.5] undesano dietil] 1,2,3,4-butantetra-sarboxilate mixed, [1,2,2,6,6-pentamethylpiperidin-4-yl / ß, ß, ß ', ß' -tetramethyl -3, 9- (2,4,8,10-tetraoxa-spiro [5.5] undesano) diethyl]) 1,2,3,4-butantetracarboxylate mixed, ostamethylene bis (2, 2,6,6-tetramethylpiperidin-4) -sarboxylate), 4,4'-ethylenebis (2,2,6,6-tetramethylpiperazin-3-one), N-2, 2,6,6-tetramethylpiperidin-4-yl-n-dodesylsussinimide, Nl, 2, 2,6,6-pentamethylpiperidin-4-yl-n-dodesylsussimide, Nl-asethyl -2,6,6,6-tetra-methylpiperidin-4-yl-n-dodesilylsiminide, l-asethyl-3-dodesyl-7,7,9,9-tetramethyl-l, 3,8-triazaspiro [5.5] -desan- 2,4-dione, di- (l-octyloxy-2,6,6,6-tetramethylpiperidin-4-yl) sebacate, di- (l-cislohexyloxy-2,6,6,6-tetramethylpiperidin-4-yl) sussinato, l-ostyloxy-2, 2,6,6,6-tetramethyl-4-hydroxy-piperidine, poly. { [6-ter-ostylamino-s-triazin-2,4-diyl] [2- (l-sislohexyloxy-2, 2,6,6-tetramethylpiperidin-4-yl) imino-hexa-methylene- [4- (l -islohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl) -imino], and 2,4,6-tris [N- (1-sislohexyloxy-2, 2,6,6-tetramethyl-piperidin-4) -yl) -n-butylamino] -s-triazine. A most preferred hindered amine moiety is bis (2,2,6,6-tetramethylpiperidin-4-yl) sebasate, bis (1,2,2,6,6-pentamethylpiperidin-4-yl) sebasate, di (1). 2, 2, 6, 6-pentamethyl-piperidin-4-yl) (3,5-di-tert-butyl-4-hydroxybenzyl) -butylmalonate, the polysondensation prodrug of l- (2-hydroxyethyl) -2 , 2,6,6-tetramethyl-4-hydroxy-piperidine and asid sussiniso, the polysondensation prodrug of 2,4-disloro-6-ter-ostil-amino-s-triazine and 4,4'-hexamethylenebis (ami no - 2, 2,6,6-tetramethyl-piperidine), N, N ', N ", N"' -tetrakis [(4, 6-bis (butyl- (2, 2, 6, 6-tetramethyl-piperidin-4-yl) amino) -s-triazine-2-yl] -1,10-di ami-4,7-diazadecane , di- (l-ostyloxy-2, 2,6,6-tetramethyl-piperidin-4-yl) sebasate, di- (l-sislohexyloxy-2, 2,6,6-tetramethylpiperidin-4-yl) sussinate, 1-ostyl? i-2, 2,6,6-tetramethyl-4-hydroxy-piperidine, poly-. { [6-ter-ostylamino-s-triazin-2,4-diyl] [2- (1-sislohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl) imino-hexamethylene- [4- (1-cis-hexhexyloxy -2,2,6,6-tetramethylpiperidin-4-yl) imino], or 2,4,6-tris [N- (l-sislohexyloxy-2, 2,6,6-tetramethyl-piperidin-4-yl) -n-butylamino] -s-triazine. The following examples are for illustrative purposes only and should not be considered as limiting the scope of the present invention in any way. Example 1, 3-Bis. { l- [2,4-Dihydroxy-5- (3,5-di (biphenylyl) -s-triazinyl)) -phenyl] -l-methyl-ethyl} benzene To a 500 ml three-necked round bottom flask equipped with a magnetic stirrer, condenser, thermometer and nitrogen atmosphere, it is charged to 2- (2,4-dihydroxy-phenyl) -4,6-di ( biphenylyl) -s-triazine and a catalytic amount of aluminum isopropoxide. The mixture is heated to 185 ° C and 1,3-diisopropenylbenzene is added immediately. The temperature is lowered to 132 ° C and the mixture is stirred for six hours.After cooling to room temperature, the mixture is diluted with ethyl acetate, washed twice with water and once with brine.The organic layer is dried over Anhydrous magnesium sulfate and filter The organic solvent is removed under reduced pressure The crude prodrug is purified by medium pressure chromatography using 12% ethyl acetate / heptane, to give the title compound Bjeaplp 2 Methylene-Bis Mixture -2- (2-hydroxy-4-octyloxyphenyl) -4,6-di- (biphenylylphenyl) -s-triazine; bifined at positions 3: 5, 5: 5 and 3: 3 in a ratio of 5: 4: 1 A 2- (2-hydroxy-4-octyloxyphenyl) -4,6-di (biphenylyl-phenyl) -s-triazine is charged to a round bottom flask with 250 mL sapacity, equipped with condenser, magnetic stirrer and nitrogen atmosphere. , diethoxymethane, a catalytic amount of p-toluenesulfonic acid and dioxane. The mixture is stirred at 90 * C for 28 hours and then allowed to cool to room temperature and diluted with a portion of ethyl acetate. The mixture is washed three times with water, three times with saturated sodium bicarbonate solution and then with brine. The organic layer is dried over anhydrous magnesium sulfate and filtered. The organic solvent is removed under reduced pressure to result in a crystal. The crude product is purified by mean pressure chromatography with heptane-ethyl acetate 19: 1 to result in the mixture of bridged dimer with methylene or a glassy solid. This mixture is adapted to formula II where t is 0. There are also small amounts of traces of "oligóraeros" superiors where t is 1, 2 and / or 3, seen in the spectral analysis of this product of mixed isomers.

Benzylidene-bis-2- (2-hydroxy-4-octyloxyphenyl) -4,6-di (biphenylyl) -s-triazine mixture; bridged in positions 3: 5 and 5: 5 in a 1: 1 ratio To a 250 mL round bottom flask equipped with condenser, magnetic stirrer and nitrogen atmosphere are charged 2- (2-hydroxy-4-ostyloxy phenyl) -4,6-di- (ifenyl) -) - s- triazine, benzaldehyde and a satalitic holiness of p-toluenesulfonic acid. The mixture is stirred at 140 * C for three hours, and then allowed to cool to room temperature. The mixture is taken up in ethyl acetate and washed twice with saturated sodium bicarbonate, once they are water and then with brine. The organic layer is dried over anhydrous magnesium sulfate and filtered. The organic solvent and excess benzaldehyde are removed under reduced pressure to result in a crude product which is then purified with medium pressure chromatography with heptane: ethyl acetate 19: 1, to result in the mixture of bridged diramer are benzylidene. This mixture fits the formula VI where t is 0 and L is benzylidene. EXAMPLE 4 Clear Decay Resistance of Clear Coatings Acrylic Thermofix with High Solids Content Containing UV Absorbents Applied on UV Transparent Base Coatings Test panels are prepared by spinning a film with a thickness of 0.036-0.051 mm (1.8-2.0) mils) of a clear acrylic melamine coating of commercially available high solids content, containing 2% by weight based on the melamine acrylic resin of the UV absorbent of example 2, on a commercially available UV transparent basecoat, wet-in-wet. The top coating is applied to UNIPRIME * 4 * 10.16 sm x 30.48 cm (4 inches x 12 inches) panels obtained from Advance Coatings Technology, Inc. The coated panels are then baked at 121"C (250ßF) for 30 minutes. storage for a week in an air-conditioned room, the panels are exposed in a Florida black box to South 5ß according to SAE J-1976. The panels are exposed for one year. humidity consisting of exposing the panels to 38 * C (100 * F) and 100% humidity for four days.After four days, an adhesion test is performed with tape.

The present compounds are effective in improving the adhesion of the clearcoat to the basecoat during interation.

Resistance to Delamination of Clear Coatings of Acrylic Urethane which Contain UV Absorbents Applied Directly onto Electro-coating Primer Test panels are prepared by application of film coating are thickness of 0.036-0.051 mra (1.8-2.0 mils) of a clear coating of commercially available acrylic urethane containing 2% by weight based on urethane acrylic resin, of a UV-absorbent test of Example 3, directly on UNIPRIME "* panels of 10.16 cm x 30.48 cm (4 inches x 12 inches) obtained from Advance Coatings Technology, Inc. The coated panels are then baked at 121 * C (250 * F) per minutes. After storage for a week in an air-conditioned room, the panels are displayed in a Florida 5 * South black box according to SAE J-1976. The panels are evaluated each day by delamination and are removed from the test when it is evident delamination over 10% of the panel area. The present compounds are effective in delaying the delamination of the clear coating of the electrocoating primer.

EXAMPLE The following example demonstrates the utility of the o-hydroxyphenyl-s-triazines of the present invention in a laminated polycarbonate plate where the UV absorber is incorporated only in the thin-skin protective layer, as prepared in an article so-extruded. Laminated plates are prepared by bonding 0.0254 mm (1 mil) polycarbonate film (LEXAN1"141-111N), General Electric Co.) containing 5% by weight of a UV absorbent of the present example 1 or 2 to a polycarbonate plate 3.18 mm (125 mil) non-UV stabilized (LEXAN * "141-111N) by compression molding in a Wabash Compression Shaper at 177aC (350ßF) for three minutes at 70 Kg / cma (1000 psi), three minutes at 210 Kg / cma (3000 psi) and then three minutes at 210 Kg / cma (3000 psi) while cooling. The plates are then exposed on an Atlas CI-65 Xenon Arc Weather Tester using Test Method C of the designation G26-88 ASTM with the protective layer directed to incident light. The degradation of polymer is determined by measuring Yellow Index (Y) in an ACS spectrophotometer. The o-hydroxyphenyl-s-triazines of the present invention are very effective in protecting the polycarbonate sheet from degradation and discoloration.

Ejeaplc- 7 Samples of polypropylene fibers are prepared by extruding fiber grade polypropylene containing a pigment, a phosphite, a phenolic antioxidant or hydroxylamine, a metal stearate, a UV absorber, or hindered amine light stabilizer or a combination of UV absorber and hindered amine light stabilizer. The pigment is added as a pigment concentrate that is prepared from pure pigment and polypropylene resin (PROFAXMR 6301, Himont) by mixing the two components in a high shear mixer in a ratio of 25% pigment and 75% resin , press the resultant pigment / resin mixture into a Wabash Compression Mold (Model # 30-1515-4T3) on a thin sheet and then divide the sheet into fine pieces by dispersing in fresh polypropylene resin at redused concentrations. All the additive and pigment soncerations in the final formulations are expressed as weight percent based on the resin. The formulations contain 0.05-0.1% phosphite, 0-1.25% antioxidant phenoxy, 0-0.1% hydroxylamine, or 0.01-0.1% salsium stearate, 0-1.25% UV absorber of present example 2 or 3 and / or 0-1.25% hindered amine stabilizer. The materials are blended into a drummer dough, prosed in a single spindle / MPM 2.54 cm (1 inch) extruder with a general purpose spindle (24: 1 L / D) at 246ßC (475 * F) , cooled in a water bath and pellet. The resulting beads are centrifuged to a fiber at approximately 274ßC (525ßF) in a HILLS Research Fiber Extruder (Model # REM-3P-24) coupled with a 41-hole delta configuration centrifuge nozzle. The centrifuged mesha is stretched to an extrasion propulsion of 3.2: 1 producing a final denier of 615/41. The fiber samples are woven in socks in a Lawson-Hemphill Fiber Analysis Weaver, cut into appropriate sections and expose Atlas CEN65 Intemperl etro Atlas at black panel temperature of 89 ° C, 0.55 W / m at 340 nanometers and 50% relative humidity (test procedure of the Society of Automotive Engineers (Society of Automotive Engineers) SAE J 1885). Samples of fibers are tested by performing color measurements on a Spectrophotometer from Applied Color Systems by reflectance mode to ASTM D 2244-79 at regular intervals. Identical but separate samples are examined for catastrophic failure. The test results show that the combination of a UV light absorber of this invention with a hindered amine provides much greater protection to the pigmented polypropylene fiber, no doubt ßinergysic stabilization protection over the level of protection provided by the hindered amine alone. when the same total consentration is used. The same superior stabilization is seen when the pigmented polypropylene fiber is replaced with nylon fiber or pigmented polyester.

Claims (16)

1. RBIYIHD-ICACICTKBS 1. A compound of the formula where Gx is a group of the formula
2. G2 is a group of the formula where q is 0 or 1, Rx, a, R », < , R ", Rβ, R7, R., R, and R1Q independently of each other are hydrogen, hydroxyl, cyano, alkyl with 1 to 20 carbon atoms, alkoxy with 1 to 20 carbon atoms, phenylalkyl with 7 to 15 carbon atoms, carbon, cisloalkyl are 4 to 12 atoms of sarbon, sicloalkoxy are 4 to 12 carbon atoms, halogen, haloalkyl with 1 to 5 carbon atoms, sulfonyl, carboxyl, asylamino of 2 to 12 carbon atoms, acyloxy with 2 to 12 atoms of carbon, alkoxycarbonyl with 2 to 12 atoms of sarbon, aminocarbonyl or R3 and R, together are the phenyl radical to which they are connected, they are a cyclic radical interrupted by one or more oxygen or nitrogen atoms, Ea is hydrogen, straight chain alkyl or branched co to 1 to 24 carbon atoms or cycloalkyl with 5 to 12 carbon atoms; or the alkyl or cycloalkyl substituted by one to eight halogen, epoxy, glycidyloxy, furyloxy, -E4, -0Ea, -N (ES) 2, -C0N (Eß) 2, -CONfE ») ^ -COEs, -C00Es, - OCOE ,,, -0C0C (EB) = C (Es) a, -C (E5) »CC00Ea, -CN, -NCO, or its sombinasiones; or the alkyl or cycloalkyl interrupted by one to six epoxy, -O-, -NE9-, -C0NEß-, -COO-, -0C0-, -CO-, -C (Eß) = C (E5) C00-, - 0C0C (Es) = C (E5) -, - (E8) C * C (EB) -, phenylene or -phenylene-Gj-phenylene wherein Gs is -0-, -S-, -S03-, -CHa- , or -C (CH ») a-, or combinations thereof; or the alkyl or cisloalkyl both substituted and interrupted by combinations of the aforementioned groups; or Ea is -SOaE, or -C0E6; E4 is aryl is 6 to 10 carbon atoms, or aryl substituted by one to three halogen atoms, alkyl with 1 to 8 carbon atoms, alkoxy with 1 to 3 carbon atoms or combinations thereof; cycloalkyl with 5 to 12 carbon atoms; or phenyl-C7-C15-alkyl or the phenylalkyl substituted on the phenyl ring by one to three halogen atoms, alkyl with 1 to 10 carbon atoms, alkoxy with 1 to 3 carbon atoms or combinations thereof; or straight or branched chain alkenyl with 2 to 18 sarbone atoms; E5 is defined as E4, or E "is also hydrogen or branched or substituted chain alkyl of 1 to 24 carbon atoms; or E5 is a group of the formula wherein Tt is hydrogen, oxyl, hydroxyl, alkyl having 1 to 12 carbon atoms, the alkyl is substituted at least by a hydroxyl or lower alkyl, benzyl or alkanoyl having 2 to 18 sarbone atoms; Eß is straight or branched chain alkyl with 1 to 18 carbon atoms, straight or branched chain alkenyl with 2 to 18 carbon atoms, phenyl, alkoxy with 1 to 12 carbon atoms, phenoxy, alkylamino with 1 to 12 carbon atoms. carbon, arylamino with 6 9 12 carbon atoms or a group -E7C00H or -NH-Eß-NCO; E7 is alkylene with 2 to 14 carbon atoms or o-phenylene; E 'is alkylene with 2 to 10 carbon atoms, phenylene, toluene, diphenylenemethane or a group t is 0 to 9; and L is straight or branched chain alkylene with 1 to 12 carbon atoms, cycloalkylene with 5 to 12 carbon atoms, alkylene substituted or interrupted by cislohexylene or phenylene; or L is benzylidene; or L is -S-, -SS-, - "S- S-S-, -SO-, -SOa-, -SO-I ^ -SO-, -SOa-Li-SO, -, -CHa-NH -L? -NH-CHa- or wherein L% is alkylene with 2 to 12 atoms of sarbon, siloalkylene with 5 to 12 carbon atoms or alkylene interrupted or terminated by cyclohexylene with 8 to 12 carbon atoms; with the proviso that at least one bond L is connected to the phenyl ring in the -5 position. 2. A compound in accordance with the claim 1, characterized in that Gt and G3 are biphenylyl or biphenylyl substituted with one to three lower alkyl or halogen; Ea is hydrogen or straight or branched chain alkyl of 2 to 24 carbon atoms or the alkyl substituted by one or two -0Eß, wherein EB is hydrogen, straight or branched chain alkyl with 1 to 24 carbon atoms or phenyl; L is alkylene with 1 to 12 carbon atoms, or the alkylene substituted by cyclohexyl or phenyl or intß-trurapido by cyclohexylene or phenylene.
3. 3. A composition of the formula I according to claim 1, characterized in that d, and Ga are biphenylyl or biphenylyl substituted with one to three lower alkyl or halogenol; E2 is alkyl with 2 to 24 carbon atoms substituted by a hydroxy and a -0Eβ wherein E * is alkyl with 1 to 24 carbon atoms or phenyl; t is 0 to 3; and L is methylene; benzylidene;
4. 4. A compliant compound is claim 1, characterized in that q is 1, t is 0 and Rl R2, Ra, R4, ß, R «, R ,, R ,, R" and io each are hydrogen.
5. 5. A compound according to claim 1, characterized in that Gx and Ga are 4-biphenylyl; t is 0; It is carbon or the alkyl substituted by a hydroxyl and by a -0ES wherein Ea is alkyl with 1 to 24 sarbone atoms; L is methylene, benzylideho or alkylene are 4 to 8 carbon atoms which is interrupted by phenylene.
6. 6. A compliant compound is the claim 1, characterized in that it is l, 3-bis. { l- [2,4-Dihydroxy-5- (3,5-di (4-biphenylyl) -s-triazinyl)) phenyl] -l-methyl-ethyl} benzene; mixture of methylene-bis- [2- (2-hydroxy-4-octyloxyphenyl) -4,6-di (4-biphenylyl) -s-triazine bridged in the 3: 5, 5: 5 and 3: 3 positions in a ratio of 5: 4 * 1; and mixture of benzylidene-bis- [2- (2-hydroxy-4-ostyloxyphenyl) -4,6-di- (4-biphenylyl) -s-triazine; bridged in the 3: 5 and 5: 5 positions in a ratio lll.
7. 7. A composition stabilized against the deleterious effects of actinic radiation, sarasterized because it is: (a) an organic material subject to degradation when exposed to actinic radiation, and (b) an effective stabilizing amount of a compound of formula I of according to claim 1.
8. 8. A composition according to claim 7, sarasterized in that the organo material of the somponent (a) is a polymer.
9. 9. A soundness composition according to claim 8, characterized in that the polymer is a high-content solid-state silicone / melamine resin or a urethane urethane resin.
10. 10. A compliance composition is claim 8, characterized in that the composition is a polymeric film composition comprising (a) an electrocoating primer adhered to a metal substrate, (b) a base or color coating that adheres to the substrate. electrocoating and comprising a film fodder binder and an organic pigment or an organic pigment or mixtures thereof, (c) a transparent coating that adheres to the base coat and comprises a film-forming binder, and (d) an amount effective stabilizer of at least one tris-aryl-s-triazine UV absorber of the formula I contained either in the basecoat or in the clearcoat or both the basecoat and clearcoat
11. 11. A composition in accordance with claim 7, characterized in that component (b) is between 1 and 20% by weight of component (a).
12. 12. A composition according to claim 10, characterized in that the component (d) is incorporated in the base coat.
13. 13. A composition according to claim 8, characterized in that it additionally contains an effective amount of stabilizer of at least one 2-hydroxy-phenyl-2H-benzotriazole; another tris-aryl-s-triazine; or hindered amine light stabilizer or mixtures thereof.
14. 14. A composition in accordance with claim 13, characterized in that 2-hydroxy-phenyl-2H-benzotriazole is selected from the group consisting of: 2- (2-hydroxy-3,5-di-ter-aroyl-phenyl) -2H-benzotr-aiazole; 2- [2-hydroxy-3,5-di (a, a-dimethylbenzyl) phenyl] -2H-benzotriazole; 2- [2-hydroxy-3- (a, a-dimethylbenzyl) -5-octylphenylJ-2H-benzotriazole; 2-. { 2-hydroxy-3-tert-butyl-5- [2- (omega-hydroxy-octa (ethyleneoxy) -carbonyl) ethyl] -fnyl) -2H-benzotriazole; and 2-. { 2-hydroxy-3-tert-butyl-5- [2- (octyloxy) sarbonyl) ethyl] phenyl} -2H-benzotriazole; the other tri-aryl-s-triazine is selected from the group consisting of 2,4-bis (2,4-dimethylphenyl) ~ 6- (2-hydroxy-4-octyloxyphenyl) -s-triazine; 2,4-dif ßnil-6- (2-hydroxy-4-hexy loxif eni 1) -s-triazine; and 2,4-bis (2,4-diraethylphenyl) -6- [2-hydroxy-4 ~ (3-do- / tri-decyloxy-2-hydroxy-propo? i) enyl] -s-triazine; and the hindered amine is selected from the group consisting of bis (2,2,6,6-tetramethyl-piperidin-4-yl) sebacate, bis (1,2,2,6,6-pentamethylpiper idin-4-i 1) sebasato, di (1, 2, 2), 6, 6-pentamethylpiperidin-4-yl) (3,5-di'-tert-butyl-4-hydroxybenzyl) butylmalonate, 4-benzoyl-2,2,6,6-tetramethylpiperidine, 4-stearyloxy-2, 2 , 6, 6 -tetrameti Ipiperidine, 3-n-scti 1-7, 7,9, 9-tetramethyl-l, 3, 8-triaza-spiro [.5 Jdecan-2, -dione, tris (2, 2, 6,6-t-tetramethylpiperidin-4-yl) nitrilotriasetate, 1,2-bis (2,2,6,6-tetramethyl-3-oxopiperazin-4-yl) ethane, 2,2,4,4-tetramethyl- 7-oxa-3, 20-diaza-21-oxodiespiro- [5.1.11.2} heneisosan, polysondensation product of 2,4-disloro-6-ter-octylamino-s-triazine and 4,4 '-hexame and lenbis (araino-, 2,6,6-tetramethylpiperidine), polycondensation product of l- ( 2-hydroxyethyl) -2,2,6,6-tetramethyl-4-hydroxypiperidine and sucsinis acid, polycondensation prodrug of 4,4'-hexamethylenebis- (amino-2,2,6,6-tetra-methylpiperidine) and 1 , 2-dibromoethane, tetrakis (2, 2, 6,6-tetramethylpiperidin-4-yl) 1,2,3,4-butantetrasarboxylate, tetrakis (1,2,2,6,6-pentaraethylpiperidin-4-yl) 1 , 2,3,4-butan-tetrasarboxylate, polycondensation product of 2, -dichloro-6-morpholino-s-triazine and 4,4'-hexamethylenebis (amino-2,2,6,6-tetramethylpiperidine), N , N ', N ", N"' - tetrakis £ (, 6-bis (butyl-2, 2,6,6-tetramethyl-pipßridin-4-yl) -amino-s-triazin-2-yl] -1 , 10-diamino-4, -diazadecane, [2,2,6,6-tetramethylpiperidin-4-yl / ß, ñ, ß ', ß'-tetramethyl-3,9- (2,4,8, l? -tetra-oxaespiro [5.5] undesan) diethyl] 1,2,3,4-butantetracarboxylate mixed, [1, 2,2,6,6-pentaraethylpiperidin-4-] il / ß, ß, ß ', ß'-tetramethyl-3,9- (2,4,8,10-tetraoxa-spiro [5.5] undecan) dieti 1] -1, 2, 3, -butantetrasarboxy lato mixed, octameti lenbis (2,2,6,6-tetramethylpiperidin-4-carboxylate), 4'-et i-lebis (2,2,6,6-tetramethylpiperazin-3-one), N-2, 2 , 6,6-tetramethylpiperidin-4-yl-n-dodysilyl succinimide, Nl, 2, 2, 6, 6-pentamethylpiperidin-4-yl-n-dodesylsuccinimide, N-1-acetyl-2,2,6,6-tetramethyl ? iperidin-4-yln-dodecyl succinimide, l-acetyl-3-dodecyl-, 7,9,9-tetramethyl-l, 3,8-triazaspiro [4.5] decan-2,4-dione, di- (l-octyloxy-2) , 2,6,6-6-tetramethylpiperidin-4-i 1) sebacate, di- (1-cyclohexyloxy-2, 2,6,6-tetramethylpiperidin-4-yl) succinate, 1-octyloxy-2,2,6, 6-tetrahydro-4-hydroxy-piperidine, poly-. { [6-ter-ostylamino-s-triazin-2,4-diyl] [2- (l-sislohexyloxy-2,6,6,6-tetramethyl-piperidin-4-yl) iraino-hexamidethylene [4- (l- cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl) imino], and 2,4,6-tris [N- (l-sislohexyloxy-2,2,6,6-tetramethylpiperidin-4-i1) - n-butylamino] -s-triazine.
15. 15. Use of a compound of formula I according to claim 1 as a stabilizer to protect an organic material against degradation caused by light, oxygen and salor.
16. 16. A process for stabilizing an organic material against degradation caused by light, oxygen and heat, this process comprises incorporating to the material at least one compound of the formula I according to claim 1.