WO2008083975A1 - Light-stabilized composition - Google Patents

Light-stabilized composition Download PDF

Info

Publication number
WO2008083975A1
WO2008083975A1 PCT/EP2008/000173 EP2008000173W WO2008083975A1 WO 2008083975 A1 WO2008083975 A1 WO 2008083975A1 EP 2008000173 W EP2008000173 W EP 2008000173W WO 2008083975 A1 WO2008083975 A1 WO 2008083975A1
Authority
WO
WIPO (PCT)
Prior art keywords
radical
bis
unsubstituted
mono
substituted
Prior art date
Application number
PCT/EP2008/000173
Other languages
French (fr)
Inventor
Olga Gorchs Capa
Oscar Jimenez Alonso
Carlos Ramon Trullas Cabanas
Jordi Corbera Arjona
David Panyella Costa
Original Assignee
Isdin S.A.
Antonio Puig, S.A.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Isdin S.A., Antonio Puig, S.A. filed Critical Isdin S.A.
Publication of WO2008083975A1 publication Critical patent/WO2008083975A1/en

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D487/00Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/12Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
    • C07D487/16Peri-condensed systems
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00Use of organic ingredients
    • C08K5/16Nitrogen-containing compounds
    • C08K5/34Heterocyclic compounds having nitrogen in the ring
    • C08K5/3467Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
    • C08K5/3477Six-membered rings
    • C08K5/3492Triazines

Definitions

  • the present invention relates to a light-stabilized composition
  • a light-stabilized composition comprising at least one polymer and 0.01 to 25 % by weight, based on the total weight of the composition, of a light-stabilizing component comprising at least one heptaazaphenalene compound of general formula (I),
  • radicals R 1 , R 2 and R 3 are defined in the description, optionally in combination with at least one further light stabilizer (Z), to articles, moulds, sheets, foils or films produced of such light-stabilized composition, to the use of at least one heptaazaphenalene compound of general formula (I) as a light stabilizer for polymers as well as to a light stabilizer combination comprising at least one of said heptaazaphenalene and at least one further light-stabilizer (Z).
  • Polymer compositions of various kinds are useful materials for many applications and are used in various industries as raw material for the production of various items such as for example articles or moulds of different size and shape, sheets, films, foils, paintings, coatings, as part of an end product or as end product for the consumer.
  • Polymer compositions with high quality are replacing other materials such as glass, metal, paper and wood in an increasing extent.
  • polymer compositions or articles thereof can be subject to rapid and severe degradation/deterioration because of exposure to light, impairing the mechanical properties like impact strength, flexibility or elasticity and causing discoloration, surface cracking or loss of gloss.
  • polymer compositions which are light stabilized, which means effectively protected against harmful degradation or decomposition caused/induced by light, such as e.g. UV light, sunlight or fluorescent indoor light.
  • a light- stabilizing component comprising at least one heptaazaphenalene compound of general formula (I),
  • Such inventive, light-stabilized compositions show an effective protection against deteriorating effects resulting from light exposure, preferably UV light.
  • one aspect of the present invention is a light-stabilized composition
  • a light-stabilized composition comprising at least one polymer and 0.01 to 25 % by weight, based on the total weight of the composition, of a light-stabilizing component comprising at least one heptaazaphenalene compound of general formula (I),
  • Ri, R 2 and R 3 independently of each other, each represents an unsubstituted or at least mono-substituted mono- or polycyclic aryl radical; an unsubstituted or at least mono-substituted, saturated, unsaturated or aromatic heterocyclic radical having from 5 to 10 atoms that can contain 1 , 2 or 3 heteroatoms independently selected from O, N and S; an -OR 4 radical; or a -NR5R6 radical;
  • R 4 represents a hydrogen atom; an unsubstituted or at least mono-substituted, saturated or unsaturated, linear or branched CM S aliphatic radical; an unsubstituted or at least mono-substituted 0 3 -12 cycloalkyl radical; an unsubstituted or at least mono-substituted mono- or polycyclic aryl radical; an unsubstituted or at least mono- substituted, saturated, unsaturated or aromatic heterocyclic radical having from 5 to 14 atoms that can contain 1 , 2 or 3 heteroatoms independently selected from O, N and S; R 5 and R 6 , independent of each other, each represents a hydrogen atom; an unsubstituted or at least mono-substituted, saturated or unsaturated, linear or branched C MS aliphatic radical; an unsubstituted or at least mono-substituted C 3- -I 2 cycloalkyl radical; an unsubstitute
  • R 5 and Re form together with the bridging nitrogen atom an unsubstituted or at least mono-substituted saturated, unsaturated or aromatic mono- or polycyclic ring system having from 4 to 10 atoms that contains optionally 1 or 2 heteroatoms independently selected from N, O and S;
  • radicals R-i, R 2 and R 3 are identical, R 1 , R 2 and R 3 shall at the same time not represent an unsubstituted phenyl radical;
  • R 4 shall not represent a hydrogen atom or a radical selected from the group consisting of n-butyl, ethyl, phenyl, benzyl, 2,6- dimethylphenyl, 3,5-dimethylphenyl, 2,2,3,3,4,4,4-heptafluorobutyl, 2,2,3,3,3- pentafluoropropyl, 2,2,2-trifluoroethyl and hydroxymethyl;
  • R 4 represents an ethyl radical for two of the radicals Ri, R 2 and R 3 , then R 4 shall not represent a hydrogen atom for the remaining third radical of the radicals Ri, R 2 and R 3 ; preferably with the proviso that if each of the radicals R 1 , R 2 and R 3 represent a
  • R 5 and R 6 shall not represent a radical selected from the group consisting of ethyl, n-butyl, benzyl, n- heptyl, unsubstituted phenyl, cyclohexyl, 2-pyridyl and hydroxymethyl;
  • R 5 and R 6 radical at the same time and if either R 5 or R 6 represents a hydrogen atom, then the other one of the radicals R 5 and R 6 shall not represent a radical selected from the group consisting of n-butyl, unsubstituted phenyl, hydroxymethyl, 4- methoxy-9,10-dihydro-9,10-dioxoanthracene-1-yl, 9,10-dihydro-9,10- dioxoanthracene-1-yl, 9,10-dihydro-9,10-dioxoanthracene-2-yl and 5-benzoylamino- 9,10-dihydro-9,10-dioxoanthracene-1-yl;
  • each of the radicals R 1 , R 2 and R 3 each represents a -NR 5 R 6 radical at the same time, and if each of the radicals R 5 and R 6 represent at the same time a n-heptyl radical for two of the radicals Ri, R 2 , and R 3 , then each of the radicals R 5 and R 6 of the third radical shall not represent a phenyl radical at the same time;
  • each of the radicals R 1 , R 2 and R 3 represent a - NR 5 R 6 radical at the same time, and if each of the radicals R 5 and R 6 represent at the same time a phenyl radical for two of the radicals R 1 , R 2 and R 3 , then each of the radicals R 5 and R 6 of the third radical shall not represent a n-heptyl radical at the same time.
  • composition comprising 3% by weight of 2,5,8-tris-(4- (butoxycarbonyl)phenylamino)-1 ,3,4,6,7,9, 9b-heptaazaphenalene
  • composition comprising 6% by weight of 2-(4- (carboxy)phenylamino)-5,8-bis-(4-methylphenyl)-1 ,3, 4,6,7,9, 9b-heptaazaphenalene
  • composition comprising 6% by weight of 2,5,8-tris-(4-(2- ethylhexyloxycarbonyl)phenylamino)-1 ,3, 4,6,7,9,9b-heptaazaphenalene
  • ethylhexyl methoxycinnamate based on the weight of the combination of 2,5,8-tris-(4-(butoxycarbonyl)phenylamino)-1 ,3,4,6,7,9 > 9b- heptaazaphenalene and ethylhexyl methoxycinnamate;
  • titanium dioxide based on the weight of the combination of 2-(4-(carboxy)phenylamino)-5,8-bis-(4-methylphenyl)-1 ,3, 4,6,7,9,9b- heptaazaphenalene and titanium dioxide;
  • titanium dioxide 32.4 - 39.5% by weight of titanium dioxide, based on the weight of the combination of 2,5,8-tris-(4-(2-ethylhexyloxycarbonyl)phenylamino)-1 ,3, 4,6,7,9,9b- heptaazaphenalene and titanium dioxide.
  • light stabilizer means, according to the present invention a chemical compound that protects the material like a polymer against photodegradation against deterioriating and/or decomposing effects caused by its exposure to light.
  • photostabilizer also referred to as "photostabilizer” or “photoprotecting agent”
  • photoprotecting agent means, according to the present invention a chemical compound that protects the material like a polymer against photodegradation against deterioriating and/or decomposing effects caused by its exposure to light.
  • IUPAC International Union of Pure and Applied Chemistry
  • light stabilizers can also be classified according to their special possibility of stabilizing against the impact of light into absorbers, quenchers, peroxide decomposers or free radical scavengers.
  • absorbers and quenchers are preferably agents that reduce the impact caused by exposure to light either by absorbing, extincting, filtering, scattering, deflecting or reflecting light
  • a peroxide decomposer is preferably an agent that transforms peroxides into stable compounds without the formation of free radicals
  • a free radical scavenger is preferably an agent that eliminates free radicals by binding.
  • the inventive light-stabilized composition comprises as the light-stabilizing component at least one absorber, quencher, peroxide decomposer and/or free radical scavenger.
  • the light-stabilizing component is at least one heptaazaphenalene compound of general formulae (IA) to (IL)
  • R 1 , R' 2 and R' 3) independent of each other, each represents an unsubstituted or at least mono-substituted, mono- or polycyclic aryl radical; an unsubstituted or at least mono-substituted, saturated, unsaturated or aromatic heterocyclic radical having from 5 to 10 atoms that can contain 1 , 2 or 3 heteroatoms independently selected from O, N and S;
  • R 4 , R' 4> R ⁇ 4 and R m 4 independently of each other, each represents a hydrogen atom, an unsubstituted or at least mono-substituted, saturated or unsaturated linear or branched CM S aliphatic radical; an unsubstituted or at least mono-substituted 0 3 . 12 cycloalkyl radical; an unsubstituted or at least mono-substituted mono- or polycyclic aryl radical; an unsubstituted or at least mono-substituted saturated, unsaturated or aromatic heterocyclic radical having from 5 to 14 atoms that can contain 1 , 2 or 3 heteroatoms independently selected from O, N and S;
  • R' 5 , R n 5, R m 5, R' ⁇ . R" ⁇ and R'" 6 independently of each other, each represents a hydrogen atom; an unsubstituted or at least mono-substituted, saturated or unsaturated, linear or branched CM S aliphatic radical; an unsubstituted or at least mono-substituted C 3- - I2 cycloalkyl radical; an unsubstituted or at least mono- substituted mono- or polycyclic aryl radical; an unsubstituted or at least mono- substituted saturated, unsaturated or aromatic heterocyclic radical having from 5 to 10 atoms that can contain 1 , 2 or 3 heteroatoms independently selected from O, N and S;
  • R'5, R"5, R'"5, R' ⁇ > R" ⁇ and R"'6 form together with the bridging nitrogen atom an unsubstituted or at least mono-substituted, saturated, unsaturated or aromatic mono- or polycyclic ring system which has 5 to 10 atoms as ring members and which contains optionally 1 , 2 or 3 heteroatoms independently selected from O, N and S;
  • the light- stabilizing component is at least one heptaazaphenalene compound of general formula (IA)
  • R' 4> R" 4 and R'" 4 independent of each other, each represents an unsubstituted or at least mono-substituted, C 3- i 2 cycloalkyl radical; an unsubstituted or at least mono- substituted mono- or polycyclic aryl radical; an unsubstituted or at least mono- substituted saturated, unsaturated or aromatic heterocyclic radical having from 5 to 14 atoms that can contain 1 , 2 or 3 heteroatoms independently selected from O, N and S;
  • R' 4 , R" 4 and R'" 4 are at the same time identical, they shall not represent phenyl, benzyl, 2,6-dimethylphenyl or 3,5-dimethylphenyl;
  • the light- stabilizing component is at least one heptaazaphenalene compound as defined above,
  • R12. Ri3, R14, R15 and Ri 6 each represents an unsubstituted or at least mono-substituted, linear or branched Ci_6 alkyl radical; an unsubstituted or at least mono-substituted, linear or branched -O-Ci -6 radical; an unsubstituted or at least mono-substituted aryl radical or an -OSi(Ri 7 ) 3 radical;
  • R 17 represents an unsubstituted or at least mono-substituted, linear or branched Ci -6 alkyl radical, an unsubstituted or at least mono-substituted, linear or branched -0-Ci -8 radical or an unsubstituted or at least mono-substituted aryl radical;
  • M represents H, Na + or K + ;
  • R 7 , R 8 and R 9 independent from each other, each represents a hydrogen atom; an unsubstituted or at least mono-substituted aryl radical; an unsubstituted or at least mono-substituted, linear or branched CM S alkyl radical; an unsubstituted or at least mono-substituted, C 3 -i 2 cycloalkyl radical; an unsubstituted or at least mono- substituted saturated, unsaturated or aromatic heterocyclic radical having from 5 to 10 atoms that can contain 1 , 2 or 3 heteroatoms independently selected from O, N and S;
  • R 8 and Rg form together with the bridging nitrogen atom an unsubstituted or at least mono-substituted, saturated, unsaturated or aromatic mono- or polycyclic ring system having from 5 to 10 atoms as ring members that contains optionally 1 or 2 heteroatoms independently selected from O, N and S;
  • R-io represents an unsubstituted or at least mono-substituted, linear or branched alkyl radical, or an unsubstituted or at least mono-substituted aryl radical,
  • Rio is fused to form a mono- or polycyclic saturated, unsaturated or aromatic ring system having from 5 to 10 atoms as ring members that contains optionally 1 or 2 heteroatoms independently selected from O, N and S;
  • R 11 represents an unsubstituted or at least mono-substituted, linear or branched alkyl radical;
  • the light- stabilizing component is at least one heptaazaphenalene compound of general formula (IB)
  • each radical represents a hydrogen atom; an unsubstituted or at least mono- substituted, linear or branched Ci-is alkyl radical; an unsubstituted or at least mono- substituted C 3 - 12 cycloalkyl radical; an unsubstituted or at least mono-substituted mono- or polycyclic aryl radical; an unsubstituted or at least mono-substituted, saturated, unsaturated or aromatic heterocyclic radical having from 5 to 10 atoms that can contain 1 , 2 or 3 heteroatoms independently selected from O, N and S;
  • R' 5 R' 6l R"s R"6, or R'" 5 R'"6 form together with the bridging nitrogen atom an unsubstituted or at least mono-substituted, saturated, unsaturated or aromatic mono- or polycyclic ring system having from 4 to 10 atoms as ring members that contains optionally 1 or 2 heteroatoms selected from N, O and S;
  • R' 5 R' 6 preferably with the proviso that if one of the radicals within each radical pair R' 5 R' 6) R n 5 R" 6 . and R'" 5 R'" 6 is hydrogen, the other radical is different from n-butyl, phenyl, hydroxymethyl, 4-methoxy-9,10-dihydro-9,10-dioxoanthracene-1-yl, 9,10-dihydro- 9,10-dioxoanthracene-1-yl, 9,10-dihydro-9,10-dioxoanthracene-2-yl, or 5- benzoylamino-9,10-dihydro-9,10-dioxoanthracene-1-yl;
  • the light- stabilizing component is at least one heptaazaphenalene compound as defined above,
  • Ci -6 alkyl radical an unsubstituted or at least mono-substituted, linear or branched Ci -6 alkyl radical, wherein the substituent(s) for the aforementioned -O-Ci- ⁇ radical and/or the aforementioned Ci- 6 alkyl radical represent(s) independently from each other at least one -SO 3 M radical, a -N(Rn) 2 radical, a -N(Rn) 3 + radical, or a moiety of general formula (II)
  • n O or 1 ;
  • P O, 1 , 2, 3 or 4;
  • Ri2, R13, Ri4, R1 5 and R16 each represents an unsubstituted or at least mono-substituted, linear or branched Ci -6 alkyl radical; an unsubstituted or at least mono-substituted, linear or branched -O-Ci- ⁇ radical; an unsubstituted or at least mono-substituted aryl radical or an -OSi(Ri 7 ) 3 radical; Ri 7 represents an unsubstituted or at least mono-substituted, linear or branched Cv ⁇ alkyl radical; an unsubstituted or at least mono-substituted, linear or branched -0-Ci -6 radical or an unsubstituted or at least mono-substituted aryl radical;
  • M represents H, Na + or K + ;
  • R 7 , Re and Rg each represents a hydrogen atom; an unsubstituted or at least mono-substituted aryl radical; an unsubstituted or at least mono-substituted, linear or branched C-M S alkyl radical; an unsubstituted or at least mono-substituted, 0 3 . 12 cycloalkyl radical or an unsubstituted or at least mono- substituted saturated, unsaturated or aromatic heterocyclic having from 5 to 10 atoms that can contain 1 , 2 or 3 heteroatoms independently selected from O, N and S;
  • R 8 and R 9 form together with the bridging nitrogen atom an unsubstituted or at least mono-substituted, saturated, unsaturated or aromatic mono- or polycyclic ring system having from 5 to 10 atoms that contains optionally 1 or 2 heteroatoms independently selected from O, N and S;
  • R 10 represents an unsubstituted or at least mono-substituted, saturated or unsaturated, linear or branched C 1 ⁇ alkyl radical or an unsubstituted or at least mono-substituted aryl radical;
  • R 10 is fused to form a mono- or polycyclic saturated, unsaturated or aromatic ring system having from 5 to 10 atoms that contains optionally 1 or 2 heteroatoms independently selected from O, N and S;
  • R 11 represents an unsubstituted or at least mono-substituted, linear or branched alkyl radical; preferably with the proviso that if one radical of the pair R 5 R ⁇ or optionally one radical of the pairs R'sR'e.
  • R"5R"6 or R"' 5 R'"6 represents an unsubstituted phenyl, 4- methoxy-9,10-dihydro-9,10-dioxoanthracene-1-yl, 9,10-dihydro-9,10- dioxoanthracene-1-yl, 9,10-dihydro-9,10-dioxoanthracene-2-yl, or 5-benzoylamino- 9,10-dihydro-9,10-dioxoanthracene-1-yl radical, the other radical is different from hydrogen;
  • the light- stabilizing component is at least one heptaazaphenalene compound of general formula (IC)
  • R' T , R' 2 and R' 3 each represents an unsubstituted or at least mono-substituted mono- or polycyclic aryl radical; an unsubstituted or at least mono- substituted saturated, unsaturated or aromatic heterocyclic radical having from 5 to 10 atoms that can contain 1 , 2 or 3 heteroatoms independently selected from O, N and S; preferably with the aforementioned provisos;
  • R'i, R n 2 and R'" 3 shall not at the same time represent a phenyl, methylphenyl, dimethylphenyl, trimethylphenyl, and 2,3,5,6- tetramethylphenyl;
  • the light- stabilizing component is at least one heptaazaphenalene compound as defined above,
  • Ri 8 represents a hydrogen atom; -OH; an -OR22 radical; an unsubstituted or at least mono-substituted, saturated or unsaturated, linear or branched C-M 8 alkyl radical; or an unsubstituted or at least mono-substituted, linear or branched -0-Ci -I s radical;
  • Ri 3 Ri4, Ri 5 and Ri 6 , identical or different, each represents an unsubstituted or at least mono-substituted, linear or branched CM S alkyl radical; an unsubstituted or at least mono-substituted, linear or branched -O-C- ⁇ - 6 radical; an unsubstituted or at least mono-substituted aryl radical or an -OSi(Ri 7 ) 3 radical;
  • Ru represents an unsubstituted or at least mono-substituted, linear or branched C- ⁇ - 6 alkyl radical; an unsubstituted or at least mono-substituted, linear or branched -O-Ci -6 radical or an unsubstituted or an at least mono-substituted aryl radical;
  • M represents H, Na + or K + ;
  • R 7 , Re and Rg each represents a hydrogen atom; an unsubstituted or at least mono-substituted aryl radical; an unsubstituted or at least mono-substituted, linear or branched CM S alkyl radical; an unsubstituted or at least mono-substituted, C 3 -C 12 cycloalkyl radical or an unsubstituted or at least mono- substituted saturated, unsaturated or aromatic heterocyclic radical having from 5 to 10 atoms that can contain 1 , 2 or 3 heteroatoms independently selected from O, N and S;
  • Re and Rg form together with the bridging nitrogen atom a saturated, unsaturated or aromatic mono- or polycyclic ring system having from 5 to 10 atoms as ring members that contains optionally 1 or 2 heteroatoms independently selected from O, N and S;
  • R 10 represents an unsubstituted or at least mono-substituted saturated or unsaturated, linear or branched Ci -6 alkyl radical, or an unsubstituted or at least mono-substituted aryl radical,
  • R 10 is fused to form an unsubstituted or at least mono-substituted, saturated, unsaturated or aromatic mono- or polycyclic ring system having from 5 to 10 atoms as ring members that contains optionally 1 or 2 heteroatoms independently selected from O, N and S;
  • Rn represents an unsubstituted or at least mono-substituted, linear or branched alkyl radical
  • R2 2 represents an unsubstituted or at least mono-substituted aryl radical; an unsubstituted or at least mono-substituted saturated, unsaturated or aromatic heterocyclic radical having from 5 to 10 atoms that can contain 1 , 2 or 3 heteroatoms independently selected from O, N and S; an unsubstituted or at least mono- substituted -COR 10 radical; an unsubstituted or at least mono-substituted 0 3 .
  • Ci-- I8 alkyl radical which is unsubstituted or at least mono-substituted by at least one -OH radical; a - SO 3 M radical; a -N(Rn) 2 radical; a -N(Rn) 3 + radical or by a radical of general formula (II)
  • R12, Ri3, Ri4, Ri5, R16 and M have the above defined meaning;
  • R 20 and R 21 each represents a hydrogen atom; an unsubstituted or at least mono-substituted, saturated or unsaturated, linear or branched d- 6 alkyl radical; an unsubstituted or at least mono-substituted, linear or branched -0-Cr 6 radical or a -SO 3 M radical, with M being H, Na + or K + ;
  • the light- stabilizing component is at least one heptaazaphenalene compound as defined above,
  • R 4 represents a radical selected from the group consisting of 4-methoxyphenyl, naphthyl, cyclopentyl and cyclohexyl;
  • R M 5, R'"5, R ⁇ > R'e, R"e and R" 6 are different from each other and each represent a hydrogen atom, cyclopropyl, cyclohexyl, cyclobutyl, cycloheptyl, cyclopentyl, 4-(hydroxycarbonyl)phenyl, 4-(butoxycarbonyl)phenyl, 4-(2- ethylhexyloxycarbonyl)phenyl, 4-(2-butyloctyloxycarbonyl)phenyl, 4-(2- hexyldecyloxycarbonyl)phenyl, 4-(3,3,5-trimethylcyclohexyloxycarbonyl)phenyl, 4- (3,3,5-trimethylhexyloxycarbonyl)phenyl, 4-(octadecyloxycarbonyl)phenyl, 4- (hexadecyloxycarbonyl)phenyl, 4-(docecyloxycarbonyl)
  • R 7 represents a hydrogen atom, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, n-pentyl, n-hexyl, 2-ethylhexyl, L-menthyl, 3,3,5-trimethylcyclohexanyl, 3,3,5- trimethylhexanyl, dodecyl, 2-butyloctyl, 2-hexyldecyl, hexadecyl, octadecyl, 3,7- dimethyloctyl , 1 ,3,3-trimethylbicyclo[2.2.1]heptan-2-yl, unsubstituted or at least mono-substituted benzyl radical or an unsubstituted or at least mono-substituted phenyl radical;
  • Re and Rg each represents a hydrogen atom, methyl, ethyl, n- propyl, isopropyl, n-butyl, tert-butyl, n-pentyl, n-hexyl, 2-ethylhexyl, L-menthyl, 3,3,5- trimethylcyclohexanyl, 3,3,5-trimethylhexanyl, dodecyl, hexadecyl, 2-butyloctyl, 2- hexyldecyl, octadecyl, 3,7-dimethyloctyl, 1 ,3,3-trimethylbicyclo[2.2.1]heptan-2-yl, unsubstituted or at least mono-substituted benzyl radical or an unsubstituted or at least mono-substituted phenyl radical;
  • Rio represents methyl, ethyl, n-propyl, n-butyl, tert-butyl or phenyl
  • Ri 7 represents methyl, ethyl, -O-CH 3 , -0-CH 2 -CH 3 or phenyl;
  • the light- stabilizing component is at least one heptaazaphenalene compound of general formula (YA)
  • R22, R23 > R24, R25. R26, R27 > R28> R29, R30 and R 3 i have the following meaning:
  • -Ph stands for a phenyl radical
  • -O-But ** stand for an -O-butyl radical
  • -O-Ac stand for an -0-acyl radical
  • the light- stabilizing component is at least one heptaazaphenalene compound of general formula (YB)
  • R 32 represents a radical selected from the group consisting of
  • the light- stabilizing component is at least one heptaazaphenalene compound of general formula (YC)
  • R 33 , R 34 and R 35 have the following meaning:
  • the light- stabilizing component is at least one heptaazaphenalene compound of general formula (YD)
  • R 36 and R 37 have the following meaning:
  • the light- stabilizing component is a heptaazaphenalene compound of formula (YE)
  • the light-stabilizing component is at least one heptaazaphenalene compound of general formula (YF)
  • R38 > R39.
  • R401 R41, R 42 and R43 have the following meaning:
  • -Ph stands for a phenyl radical
  • -CH 2 -Ph ** stand for a -CH 2 -phenyl radical
  • the light- stabilizing component is at least one heptaazaphenalene compound of general formula (YG)
  • R 44 , R4 5 and R 46 have the following meaning:
  • the light- stabilizing component is at least one heptaazaphenalene compound selected from the group comprising • 2,5,8-tris-(4-(butoxycarbonyl)phenylamino)-1 ,3,4,6,7,9, 9b-heptaazaphenalene,
  • heptaazaphenalene derivatives of general formula (I) comprised in the inventive light-stabilizing component of the inventive composition can be obtained according to the known procedures (e.g. Shroeder, H.; Kober, E. J. Org. Chem. 1962, 27, 4262).
  • a general scheme for obtaining heptaazaphenalene derivatives of general formula (I) is shown below (scheme 1 ).
  • Heptaazaphenalene derivatives of general formula (I), wherein R 1 , R 2 and R 3 are the same and represent a -NR 5 R 6 radical, wherein R 5 and R 6 have the meaning as defined above, can be obtained by reacting the 2,5,8-trichloro-1 ,3,4,6,7,9,9b- heptaazaphenalene derivative of formula (IV) with a derivative of general formula (V)
  • the microwave irradiation may be performed at a power level of 1 to 1600 W, preferably 1 to 300 W, and particularly preferably about 70 W.
  • the duration for the microwave irradiation may vary according to conditions such as the amount or reactant but may be in the range from 20 seconds to 60 minutes, preferably from 1 minute to 20 minutes.
  • the reaction can be carried out at a temperature of 50-280 0 C, preferably 80-200 0 C, and more preferably 120-150 0 C, with of without solvent, under microwave irradiation.
  • a presently preferred microwave furnace is commercially available from CEM, Inc., as model Discover®.
  • the Discover® System incorporates temperature and pressure feedback systems, for example, an infrared temperature sensor positioned below the reaction vessel, for complete control of the reaction.
  • heptaazaphenalene derivatives can be prepared within a very short time, i.e. several seconds to several minutes, by microwave irradiation, unlike conventional techniques requiring about 12-50 hours for preparation of compounds for general formula I.
  • Heptaazaphenalene derivatives of general formula (I), wherein Ri, R 2 and R 3 are different from each other and a -NR 5 R 6 radical, wherein R 5 and R 6 have the meaning as defined above, can be obtained by
  • R 5 and R 6 have the meaning as defined above, in a solvent comprising 1 ,4- dioxane, tetrahydrofuran, toluene, tetrahydrofuran, xylene (mixture of isomers), N 1 N- dimethylformamide, N-methylpyrrolidone or acetone, at a temperature that ranges between O 0 C and the boiling temperature of the solvent, preferably between room temperature and the boiling temperature of the solvent and more preferably between 5O 0 C and the boiling temperature of the solvent; optionally in the presence of an organic base comprising diisopropylethylamine, triethylamine or pyridine, or an inorganic base comprising potassium carbonate, sodium hydroxide, sodium carbonate, cesium carbonate or sodium bicarbonate; b) adding to the resulting mixture a derivative of general formula (V) different from the one used in the preceding stage
  • Ri 8 , R1 9 , R 20 and R21 have the meaning as defined above, in the presence of a Lewis acid comprising, FeCb, BF 3 , in particular aluminium trichloride, in an inert solvent comprising toluene, 1 ,1 ,2,2-tetrachloroethane, tetrahydrofuran, 1 ,2- dichlorobenzene, nitrobenzene or benzene and at a temperature that ranges between 6O 0 C and the boiling temperature of the solvent.
  • a Lewis acid comprising, FeCb, BF 3 , in particular aluminium trichloride
  • an inert solvent comprising toluene, 1 ,1 ,2,2-tetrachloroethane, tetrahydrofuran, 1 ,2- dichlorobenzene, nitrobenzene or benzene and at a temperature that ranges between 6O 0 C and the boiling temperature of the solvent.
  • Ri represents an optionally substituted mono- or polycyclic aryl radical; an optionally substituted saturated, unsaturated or aromatic heterocyclic radical having from 5 to 10 atoms that can contain 1 , 2 or 3 heteroatoms selected from O, N and S; and
  • R 5 and R 6 have the meaning as defined above, in an inert solvent comprising 1 ,4-dioxane, tetrahydrofuran, toluene, xylene (mixture of isomers), N,N-dimethylformamide, N-methylpyrrolidone or acetone, at a temperature that ranges between O 0 C and the boiling temperature of the solvent, preferably between room temperature and the boiling temperature of the solvent, and more preferably between 5O 0 C and the boiling temperature of the solvent.
  • the derivative of general formula (VII) depicted above can be obtained by reaction of the 2,5,8-trichloro-1 , 3,4,6, 7,9,9b-heptaazaphenalene derivative of general formula (V) with an optionally substituted mono- or polycyclic aryl radical; an optionally substituted saturated, unsaturated or aromatic heterocyclic radical having from 5 to 10 atoms that can contain 1 , 2 or 3 heteroatoms selected from O, N and S, in an inert solvent comprising 1 ,4-dioxane, tetrahydrofuran, toluene, xylene (mixture of isomers), N,N-dimethylformamide, N-methylpyrrolidone or acetone, at a temperature that ranges between O 0 C and the boiling temperature of the solvent, preferably between room temperature and the boiling temperature of the solvent and more preferably between 5O 0 C and the boiling temperature of the solvent.
  • the third of the radicals R 1 , R 2 and R 3 represents a -NR 5 R 6 radical, whererein R5 and R 6 are defined as defined above, can be obtained by reacting the 2,5,8-trichloro- 1 ,3,4,6, 7, 9,9b-heptaazaphenalene derivative of formula (IV) with a derivative of general formula (V)
  • R 5 and R 6 have the meaning as defined above, in a solvent comprising 1 ,4- dioxane, tetrahydrofuran, toluene, xylene (mixture of isomers), N 1 N- dimethylformamide, N-methylpyrrolidone or acetone, at a temperature that ranges between O 0 C and the boiling temperature of the solvent, preferably between room temperature and the boiling temperature of the solvent, and more preferably between 5O 0 C and the boiling temperature of the solvent, optionally in the presence of an organic base such as diisopropylethylamine, triethylamine or pyridine, or an inorganic base comprising potassium carbonate, sodium hydroxide, sodium carbonate, cesium carbonate or sodium bicarbonate to obtain a compound of general formula (VIII),
  • the compounds of general formula (I), wherein R2 0 represents a -SO3M radical, wherein M has the meaning as defined above, can be obtained by carrying out, for example, the methods disclosed in US patent 6,090,370, in particular column 5, line 59-column 6, line 8.
  • the compounds of general formula (I), wherein an -SO 3 M group, with M having the meaning as defined above, has been introduced into an alkylic chain, can be obtained according to the methods described in Lewin, G. et al., J. Nat. Prod., 58 (1995) 12, 1840-1847.
  • a further embodiment of the present invention is a combination of light stabilizers, because it has been surprisingly found that an even more efficient light protection can be achieved, if the light-stabilizing component comprises at least one hep- taazaphenalene compound as defined above and at least one further light stabilizer (Z).
  • the light-stabilized composition comprises as light-stabilizing component at least one heptaazaphenalene compound as defined above and at least one further light stabilizer (Z) selected from the group comprising acrylate derivatives, allantoin derivatives, aminobenzoic acid derivatives, aminobenzamides derivatives, anthranilic acid derivatives, benzalmalonic acid derivatives, benzimidazole derivatives, benzoate derivatives, benzophenone derivatives, benzopyranone derivatives, benzothiazole derivatives, benzotriazole derivatives, benzoxazinone derivatives, benzoxazole derivatives, camphor derivatives, cinnamate derivatives, coumarinic acid derivatives, curcumin derivatives, cycloaliphatic ketone derivatives, dianisoylmethane derivatives, dibenzalazine derivatives, dibenzoylmethane derivatives, dioxane derivatives, ferulic acid derivatives, formamidine derivatives, formanilides,
  • hindered amine mentioned above, preferably menas “sterically hindered amine”, “hindered amine light stabilizer” or “HALS".
  • HALS hindered amine light stabilizer
  • at least some of the preferably oligomeric or monomeric, hindered amine derivatives mentioned below are commercially available under their respective trade names, such as e.g.
  • DASTIB ® 845 TINUVIN ® 765, TINUVIN ® 791 , TINUVIN ® C353, TINUVIN ® XT 850, ADK STAB LA 52 ® , ADK STAB LA 57 ® , ADK STAB LA 62 ® , ADK STAB LA 63 ® , ADK STAB LA 67 ® , ADK STAB LA 68 ® , CYASORB ® UV 3581 , CYASORB ® UV 3604, SUMISORB ® TM 61 , UVINUL ® 5050 H, UVINUL ® 5062 H, DIACETAM ® 5, HOSTAVIN ® N 20, TINUVIN ® 440, TINUVIN ® 494, SANDUVOR ® 3050, HOSTAVIN ® N 24, CHIMASSORB ® 966, UVINUL ® 3434 C, UVINUL 4049 ® , GOODRITE ® UV 3034, GOODRITE
  • derivative refers to a compound in form of its respective free base, acid, salt, ester, ether, stereoisomer, such as diastereomer or enantiomer and/or solvate.
  • the light-stabilized composition comprises as light-stabilizing component at least one heptaazaphenalene compound as defined above and as further light stabilizer (Z) at least one compound of general formula (X)
  • R 1x represents a hydrogen atom; an optionally substituted cycloalkyl radical from 3 to 7 carbon atoms; an aryl radical which is unsubstituted or at least mono-substituted with a group selected from aryl, halogen, an -O-C- ⁇ -6 radical and a Ci- 6 alkyl radical; a -phenyl-Ci -6 alkyl radical; a linear or branched d- ⁇ alkyl radical which is unsubstituted or at least mono-substituted with a moiety selected from -SO 3 M X , -N(R 4x ) 3 + and a radical of general formula (XX)
  • en t o f each other, each represents an unsubstituted or at least mono-substituted C 1-6 alkyl radical; an -0-Ci -6 radical; an unsubstituted or at least mono-substituted aryl radical and an -OSi(R 10x ) 3 radical;
  • R 1Ox represents a Ci -6 alkyl radical; an -O-Ci -6 radical; or an unsubstituted or at least mono-substituted aryl radical;
  • M represents a hydrogen atom, Na + o _ _r I KX+. ;
  • R represents an unsubstituted or at least mono-substituted Ci -6 alkyl radical
  • R 2x and R 3x independently of each other, each represents a hydrogen atom; an unsubstituted or at least monosubstituted Ci -4 alkyl radical; or an unsubstituted or at least mono-substituted aryl radical;
  • a 1x represents a radical of general formula (X1 ) or (X2)
  • A represents a radical of general formula (X1 ), (X3) or (X4)
  • R represents a hydrogen atom; a linear or branched, saturated or unsaturated, unsubstituted or at least monosubstituted Ci -6 aliphatic radical; or a hydroxy (-OH) residue;
  • R 15x , R 16x and R 17x independently of each other, each represents a hydrogen atom; a linear or branched, unsubstituted or at least mono-substituted CM S alkyl radical;
  • R 14x represents hydrogen atom; or -SO 3 IvT, with M x being H, Na + or K + ;
  • R 1s represents a hydrogen atom; a linear or branched, unsubstituted or at least monosubstituted Ci -3 alkyl radical; or a R 2s R 3s" substituted phenyl- radical;
  • R j2s , D R2S' , D R3 J S S and R ⁇ 3S' • independent of each other, each represents a hydrogen atom; a halogen atom; a hydroxy (-OH) residue; an unsubstituted or at least monosubstituted Ci -3 alkyl radical; an unsubstituted or at least monosubstituted -O- Ci- 3 radical; or an unsubstituted or at least monosubstituted aryl radical;
  • R 2s and R 3s form together with the phenyl ring to which they are attached, an unsubstituted or at least mono-substituted naphthalene ring;
  • R 4s and R 5s independently of each other, each represents a hydrogen atom; an unsubstituted or at least monosubstituted C 1-4 alkyl radical; or an unsubstituted or at least mono-substituted aryl radical;
  • a 1s represents a radical of general formula (Ms), (Ills) or (IVs)
  • a k 2s represents a radical of general formula (Ms) or (Vs) wherein
  • R 6s represents a hydrogen atom; a linear or branched, unsubstituted or at least monosubstituted C- ⁇ - 6 alkyl radical; or a hydroxy (-OH) residue;
  • en t o f each other, each represents an unsubstituted or at least mono-substituted d- ⁇ alkyl radical; an unsubstituted or at least mono-substituted -O-C- ⁇ - 6 radical; an unsubstituted or at least mono-substituted aryl radical; or an -O-Si(R 21s ) 3 radical;
  • R 21s represents an unsubstituted or at least mono-substituted Ci -6 alkyl radical; an - O-C- 1 - 6 radical; an unsubstituted or at least mono-substituted aryl radical;
  • R i is R i2s anc j R i3s j nc
  • R 12s and R 13s form together with the bridging nitrogen atom an unsubstituted or at least mono-substituted, saturated 5 to 7-membered cycloaliphatic radical, which contains 1 , 2 or 3 heteroatom(s) as ring member(s) independently selected from the group consisting of O, N and S;
  • R 14s represents an unsubstituted or at least mono-substituted Ci-i 8 alkyl radical; or an unsubstituted or at least mono-substituted aryl radical;
  • R 15s represents an unsubstituted or at least mono-substituted CM S alkyl radical
  • M s represents H, Na + or K + ;
  • R 6s and R 7s form together with the phenyl ring an unsubstituted or at least monosubstituted 9 to 15-membered polycyclic ring system;
  • R 6s and R 14s form together with the phenyl ring an unsubstituted or at least mono- substituted 9 to 15-membered polycyclic ring system;
  • R 8s and R 9s independently of each other, each represents a hydrogen atom; an unsubstituted or at least monosubstituted radical; a linear or branched, saturated or unsaturated CM S aliphatic radical, which is unsubstituted or at least mono-substituted with at least one hydroxy (-OH) residue, a -SO 3 M S moiety, a -N(R 15s ) 3 + moiety or a radical of general formula (VIs) as defined above;
  • R 1Os represents a hydrogen atom; or a -SO 3 M S moiety with M s representing H, Na + or K + ;
  • W 9 represents an alkyl or an arylcyanoacrylalkyl radical
  • W 10 represents H, a phenyl or an alkylindoline radical
  • W 11 represents H or a phenyl radical
  • R m represents a linear or branched, unsubstituted or at least mono- substituted C MS alkyl radical, a phenyl radical, an unsubstituted or at least mono- substituted hydroxyphenyl radical or a hydroxyalkylether
  • R ⁇ represents H, -OH, a linear or branched, unsubstituted or at least mono-substituted CM S alkyl radical, a hydroxy(alkylether)amino radical
  • represents H, -OH or a linear or branched, unsubstituted or at least mono-substituted Ci-i 8 alkyl radical
  • R p represents H or a linear or branched, unsubstituted or at least mono-substituted C- M8 alkyl radical
  • R h represents -OH, an unsubstituted or at least mono-substituted alkoxy radical, an alkenoic acid alkoxyester radical, an aryloxy radical, a hydroxyalkoxy radical, a hydroxy(alkylether)alkoxy radical, a (polymerized acrylo)alkoxyester radical or an o-alkyl acid ester radical;
  • R' represents H, SO 3 H or SO 3 Na;
  • R j represents H or - OH;
  • R k represents H, -OH or an an unsubstituted or at least mono-substituted alkoxy radical; and
  • R 1 represents H or SO 3 Na;
  • D Rb represent -OH
  • R d represents -OH
  • R e represents a linear or branched, unsubstituted or at least mono-substituted Ci.-i ⁇ alkyl radical, an hydroxyalkyl radical, an unsubstituted or at least mono-substituted acryloxyalkyl radical, an unsubstituted or at least mono- substituted (hydroxyphenyl)alkyl radical, an unsubstituted or at least mono- substituted (alkylester)alkyl radical, an unsubstituted or at least mono-substituted (hydroxyalkylether)oxoalkyl radical or an unsubstituted or at least mono-substituted phenylalkyl radical
  • R 9 represents H or a linear or branched, unsubstituted or at least mono-substituted C- I- - I8 alkyl radical
  • R f represents Cl, Br or I
  • R s represents a linear or branched, unsubstituted or at least mono- substituted C 1 - 18 alkyl radical
  • R v represents an alkylester or a cyano moiety
  • R 1 represents a hydrogen atom or a phenyl radical
  • R u represents a hydrogen atom or an -O-Ci_i8 radical
  • W 3 , W 4 , W 5 and W 6 independently from each other, each represents a linear or branched, unsubstituted or at least mono-substituted CM S alkyl radical
  • R r and R q represent a linear or branched, unsubstituted or at least mono- substituted Ci_i 8 alkyl radical;
  • W 7 represents a hydrogen atom, a formanilide moiety, an unsubstituted or at least mono-substituted alkylalkoxy radical and/or contains a benzimidazole radical and W 8 represents a linear or branched, unsubstituted or at least mono-substituted C-1-18 alkyl radical;
  • W 1 represents an unsubstituted or at least mono-substituted -O-C-M ⁇ alkyl radical and W 1 represents a linear or branched, unsubstituted or at least mono- substituted C1-1 8 alkyl radical;
  • R c represents a linear or branched, unsubstituted or at least mono- substituted Ci- 18 alkyl radical or an unsubstituted or at least mono-substituted, saturated or unsubstituted cycloalkyl radical;
  • W 12 represents a hydrogen atom or -OH
  • W 13 represents a hydrogen atom, an unsubstituted or at least mono-substituted -0-Ci-Is alkyl radical or an unsubstituted or at least mono-substituted hydroxyalkoxy radical
  • W 14 represents a hydrogen atom or a linear or branched, unsubstituted or at least mono-substituted C
  • W 15 represents a hydrogen atom, a linear or branched, unsubstituted or at least mono-substituted Ci -I8 alkyl radical or an unsubstituted or an at least mono-substituted alkylester radical;
  • W 16 represents a hydrogen atom or a linear or branched, unsubstituted or at least mono-substituted Ci-i 8 alkyl radical and
  • W 17 represents a linear or branched, unsubstituted or at least mono-substituted CM S alkyl radical or an at least mono-substituted alkylester radical;
  • the stereoisomers preferably enantiomers or diastereomers, a racemate or a mixture of at least two of the stereoisomers, preferably enantiomers and/or diastereomers in any mixing ratio, or at least one physiologically acceptable salt and/or at least one corresponding solvate of the aforementioned compounds of general formulae (X), (Is), (L1 ), (L3), (L4), (L5), (L6), (L8), (L9), (L10), (L11 ), (L12), (L13) and (L14).
  • the compounds of general formulae (X) and (Is) mentioned above can be prepared according to WO 2006/064366 and WO 2006/128920, respectively, which relevant disclosure is herewith introduced by reference and shall form part of the description.
  • the compounds of formulae (L1), (L2), (L3), (L4), (L5), (L6), (L7), (L8), (L9), (L10), (L11 ), (L12), (L13) and (L14) mentioned above are known to those skilled in the art and can be obtained by standard techniques.
  • the light-stabilized composition comprises as light-stabilizing component at least one heptaazaphenalene compound as defined above and as further light stabilizer (Z) at least one compound selected from the group comprising isooctyl ⁇ -cyano- ⁇ , ⁇ -di- phenylacrylate, methyl ⁇ -carbomethoxycinnamate, methyl ⁇ -cyano- ⁇ -methyl-p- methoxycinnamate, butyl ⁇ -cyano- ⁇ -methyl-p-methoxy-cinnamate, methyl ⁇ - carbomethoxy-p-methoxycinnamate, N-( ⁇ -carbomethoxy- ⁇ -cyanovinyl)-2- methylindoline, ethyl-2-cyano-3,3-diphenylacrylate (UVINUL ® 3035); 2-ethylhexyl-2- cyano-3,3-diphenylacrylate (UVINUL ® 3039
  • the stereoisomers preferably enantiomers or diastereomers, a racemate or a mixture of at least two of the stereoisomers, preferably enantiomers and/or diastereomers in any mixing ratio, or at least one physiologically acceptable salt and/or at least one corresponding solvate of the aforementioned compounds.
  • the light-stabilized composition comprises as light-stabilizing component at least one heptaazaphenalene compound as defined above and as further light stabilizer (Z) at least one compound selected from the group comprising 2-ethylhexyl 2-cyano-3,3'- diphenylacrylate, ethyl 2-cyano-3,3'-diphenylacrylate, polymer of N- ⁇ (2 and 4)[(2- oxoborn-3-ylidene)methyl]benzyl ⁇ acrylamide, methyl 4-aminobenzoate, butyl 4- aminobenzoate, 5-methyl-2-(1-methylethyl)-cyclohexyl 2-aminobenzoate, glyceryl aminobenzoate, 2-ethylhexyl-p-dimethylethyl-aminobenzoate, 4-aminobenzamide, homomethyl-N-acetyl-anthranilic acid, menthyl antrhanilate
  • stereoisomers preferably enantiomers or diastereomers, a racemate or a mixture of at least two of the stereoisomers, preferably enantiomers and/or diastereomers in any mixing ratio, or at least one physiologically acceptable salt and/or at least one corresponding solvate of the afore mentioned compounds.
  • the light-stabilized composition comprises as light-stabilizing component at least one heptaazaphenalene compound selected from the group comprising
  • UVINUL ® T-150 2, 4-bis(2, 4- dihydroxyphenyl)-6-(1 -methyl-1 H-pyrazol-5-yl)-1 ,3,5-triazine, 2,4-bis ⁇ [4-(2- ethylhexyloxy)-2-hydroxy]phenyl ⁇ -6-(1-methyl-1 H-pyrazol-5-yl)-1 ,3,5-triazine, 2-[2, 4- bis (2-ethylhexyloxy)phenyl]-4-[4-(2-ethylhexyloxy)-2-hydroxyphenyl]-6-(1 -methyl-1 H- pyrazol-5-yl)-1 ,3,5- triazine, 2,4-bis(2, 4-dihydroxyphenyl)-6(1-phenyl-1 H-pyrazol-5- yl)-1 ,3,5-triazine, 2,4-bis ⁇ [4-(2-ethylhexyloxy
  • the stereoisomers preferably enantiomers or diastereomers, a racemate or a mixture of at least two of the stereoisomers, preferably enantiomers and/or diastereomers in any mixing ratio, or at least one physiologically acceptable salt and/or at least one corresponding solvate of the aforementioned compounds;
  • the stereoisomers preferably enantiomers or diastereomers, a racemate or a mixture of at least two of the stereoisomers, preferably enantiomers and/or diastereomers in any mixing ratio, or at least one physiologically acceptable salt and/or at least one corresponding solvate of the aforementioned compounds.
  • the aforementioned further light stabilizers (Z) of the inventive light-stabilizing component are already known as stabilizers.
  • the inventive composition comprises preferably 0.001 to 25 % by weight, more preferably 0.01 to 25% by weight, most preferably 0.05 to 10% by weight, based on the total weight of the composition, of the light-stabilizing component.
  • At least one of the light stabilizers of the inventive light-stabilizing component absorbs light in a wavelenth range from 100 to 700 nm, more preferably from 290 to 700 nm, most preferably from 290 to 400 nm.
  • the term "absorption" according to the present invention means any of the following ways of reducing the exposure to light radiation, like absorbing, extincting, filtering, scattering, deflecting or reflecting of light radiation, since absorption only means the ratio of transmitted radiation to the incident radiation, without determining the mechanism according to which the light radiation is reduced.
  • At least one light stabilizer of the inventive light-stabilizing component absorbs light in the range of UV-A (320 to 400 nm) and/or in the UV-B (290 to 320 nm) radiation.
  • At least one light stabilizer of the inventive light-stabilizing component has a melting point >50°C, more preferably >100°C, more preferably >150°C, most preferably >200°C.
  • the melting point for light stabilizers suitable for thermoplastic polymers is >100°C, more preferably >200°C.
  • Polymers can be preferably classified into four main groups:
  • thermoplastic polymers made of thermoplastic polymers is deformable, melts to a liquid when heated and freezes to a brittle, glassy state when cooled sufficiently.
  • Most thermoplastic polymers are high molecular weight polymers whose chains associate through weak van der Waals forces (polyethylene), stronger dipole-dipole interactions and hydrogen bonding (nylon) or even stacking of aromatic rings (polystyrene). Thermoplastic polymers can not be remelted and remolded.
  • thermosets are materials that cure, through the addition of energy, to a stronger form.
  • the energy may be in the form of heat (generally above 200 0 C), through a chemical reaction (two-part epoxy, for example), or irradiation.
  • Thermoset materials are usually liquid, powder, or malleable prior to curing, and designed to be moulded into their final form, or used as adhesives.
  • the curing process transforms the resin into a plastic or rubber by a cross-linking process.
  • Energy and/or catalysts are added that cause the molecular chains to react at chemically active sites (unsaturated or epoxy sites, for example), linking into a rigid, 3-D structure.
  • the cross-linking process forms a molecule with a larger molecular weight, resulting in a material with a higher melting point.
  • the material forms into a solid material.
  • Subsequent uncontrolled reheating of the material results in reaching the decomposition temperature before the melting point is obtained.
  • a thermoset material cannot be melted and re-shaped after it is cured.
  • Thermoset materials are generally stronger than thermoplastic materials due to this 3-D network of bonds and are also better suited to high-temperature applications up to the decomposition temperature of the material.
  • elastomer is often used interchangeably with the term rubber, and is preferred when referring to vulcanisates. They are amorphous polymers existing above their glass transition temperature, so that considerable segmental motion is possible. At ambient temperatures rubbers are thus relatively soft and deformable. Their primary uses are for seals, adhesives and molded flexible parts. 4. Coordination polymers
  • Coordination polymers are compounds where the metals are bridged by polyatomic ligands, such as e.g. cyanide or carboxylates.
  • the polymer is at least one polymer selected from the group comprising thermoplastic polymers, thermosetting polymers, elastomers and/or coordination polymers.
  • the thermoplastic polymer is at least one polymer selected from the group comprising acrylonitrile-butadiene- styrene (ABS) copolymer; cellulose derivatives such as cellulose acetate, cellulose acetate propionate, cellulose acetate butyrate, cellulose triacetate, cellulose ether, methylcellulose, ethylcellulose, propylcellulose, hydroxyethylcellulose, hydroxypropyl- cellulose, hydroxypropylmethylcellulose and carboxy methylcellulose; ethylene-vinyl acetate (EVA) copolymer; ethylene vinyl alcohol (EVAL) copolymer; polyolefines such as ethylen-propylen copolymer, ethylene-buten-1 copolymer, ethylene-hexene copolymer, ethylene-methylpentene copolymer, ethylene-heptene copolymer, ethylene octene copolymer,
  • ABS acrylonitrile-but
  • styrene-isopren-styrene block copolymer polysulfone (PSU); polyurethane (PU); polyvinyl ether; polyvinylalcohol; polyvinylidenechloride; polyvinylpyrrolidone; polyvinyl chloride (PVC); vinyl chloride- vinyl acetate copolymer; vinyl chloride-vinylidene dichloride copolymer and vinyl pyrrolidon-ethylen-vinylacetate copolymer.
  • thermosetting polymer is at least one polymer selected from the group comprising vulcanized rubber; polyoxybenzylmethylenglycolanhydride; duroplast; urea-formaldehyde resins; melamine; cured polyester resins and epoxy resins.
  • the elastomer is at least one polymer selected from the group comprising homo-, co- or block polymer of butadiene; natural rubber (NR); polyisoprene (IR); butyl rubber; halogenated butyl rubbers such as chloro butyl rubber or bromo butyl rubber; polybutadiene (BR); styrene-butadiene rubber (SBR); nitrile rubber; hydrated nitrile rubbers (HNBR); chloroprene rubber (CR); polychloroprene; neoprene; ethylene propylene rubber (EPM); ethylene propylene diene rubber (EPDM); epichlorohydrin rubber (ECO); polyacrylic rubber; silicone rubber; silicone; silcone derivatives such as siloxane- methacrylate polymers; fluorosilicone rubber; fluoroelastomers; perfluoroelastomers (FFKM); tetrafluoro
  • Polymer compositions usually comprise additives, which improve the properties of these compositions.
  • Suitable additives used in the inventive light-stabilized composition preferably include, but are not limited to anti-blocking-agents, anti- fogging agents, antistatic agents, antioxidants, biocides, blowing agents, defoamers, dyes, emulsifiers, fillers, flame retardants, heat stabilizers, impact modifiers, lubricants, metal deactivators, hydrocalcites, mould-release agents, optical brighteners, plastisizers, processing agents, pigments, phosphites, phosphonites, reinforcing agents, rheology additives, slip agents and surfactants, whereby each of these aforementioned additives is used in usual amounts known by those skilled in the art.
  • the inventive light-stabilized composition is in form of a painting, a coating, textile fibers or granulate.
  • the light-stabilizing component can be mixed with the preferably mulitparticular polymer, preferably powder or granulate, in order to prepare an inventive light- stabilized composition.
  • an inventive light- stabilized composition is prepared by premixing part of the polymer and the light stabilizer component to obtain a master batch, which is finally mixed with the residue of the polymer in order to achieve a homogeneous distribution of the light stabilizer component in the polymer.
  • the articles, moulds, sheets, foils, paintings, coatings, fibers or films, are manufactured by techniques known by those skilled in the art, using the inventive light-stabilized composition as raw material.
  • a further aspect of the present invention refers to articles, moulds, sheets, foils, paintings, coatings, fibers or films, which are produced of the inventive light-stabilized composition described above.
  • the films produced of the inventive light-stabilized composition are single-layer or multilayer films, which can be used for medical or agricultural applications.
  • the articles, moulds, sheets, foils or films, which are produced of the inventive light- stabilized composition described above are preferably suitable for outdoor carpeting, awnings, tarps, umbrellas, non-food or food-packaging applications such as rice, corn and flour bags, tapes, ropes, artificial turf, stretch-films, shrink wraps, heavy-duty bags, pool covers, garden furniture, trash cans, bottle and fruit crates, toys, interior and exterior automotive parts such as auto bumbers and interior or exterior trim, outdorr sporting and leisure goods, roofings and window shutters.
  • non-food or food-packaging applications such as rice, corn and flour bags, tapes, ropes, artificial turf, stretch-films, shrink wraps, heavy-duty bags, pool covers, garden furniture, trash cans, bottle and fruit crates, toys, interior and exterior automotive parts such as auto bumbers and interior or exterior trim, outdorr sporting and leisure goods, roofings and window shutters.
  • a further aspect of the present invention refers to the use of at least one heptaazaphenalene compound as defined above in an amount of 0.01 to 25 % by weight, based on the total weight of the composition, as a light-stabilizing component for polymers.
  • a further aspect of the present invention refers to the use of a combination comprising at least one heptaazaphenalene compound as defined above in an amount of 0.01 to 25 % by weight, based on the total weight of the composition and at least one further light-stabilizing compound (Z) selected from the group comprising acrylate derivatives, allantoin derivatives, aminobenzoic acid derivatives, aminobenzamides derivatives, anthranilic acid derivatives, benzalmalonic acid derivatives, benzimidazole derivatives, benzoate derivatives, benzophenone derivatives, benzopyranone derivatives, benzothiazole derivatives, benzotriazole derivatives, benzoxazinone derivatives, benzoxazole derivatives, camphor derivatives,
  • Another preferred embodiment of the present invention refers to the use of a combination comprising at least one heptaazaphenalene compound as defined above and at least one further light stabilizer (Z) compound of general formulae (X), (Is), (L1 ), (L2), (L3), (L4), (L5), (L6), (L7), (L8), (L9), (L10), (L11 ), (L12), (L13) and/or (L14) as defined above, in an amount of 0.01 to 25 % by weight, based on the total weight of the composition.
  • Z further light stabilizer
  • Another preferred embodiment of the present invention refers to the use of a combination comprising at least one heptaazaphenalene compound as defined above and at least one further light stabilizer (Z) selected from the group comprising ⁇ -cyano- ⁇ , ⁇ -di-phenylacrylate, methyl ⁇ -carbomethoxycinnamate, methyl ⁇ -cyano- ⁇ - methyl-p-methoxycinnamate, butyl ⁇ -cyano- ⁇ -methyl-p-methoxy-cinnamate, methyl ⁇ - carbomethoxy-p-methoxycinnamate, N-( ⁇ -carbomethoxy- ⁇ -cyanovinyl)-2- methylindoline, ethyl-2-cyano-3,3-diphenylacrylate (UVINUL ® 3035); 2-ethylhexyl-2- cyano-3,3-diphenylacrylate (UVINUL ® 3039); 1 ,3-bis-[(2'-cyano
  • a further aspect of the present invention relates to a light stabilizer combination comprising at least one heptaazaphenalene compound as defined above and at least one further light stabilizer (Z) of general formulae (L1 ), (L2), (L3), (L4), (L5), (L6), (L7), (L8), (L9), (L10), (L11 ), (L12), (L13) and/or (L14) as defined above;
  • a further aspect of the present invention relates to a light stabilizer combination comprising at least one heptaazaphenalene compound as defined above and at least one further light stabilizer (Z) selected from the group comprising isooctyl ⁇ -cyano- ⁇ , ⁇ -di-phenylacrylate, methyl ⁇ -carbomethoxycinnamate, methyl ⁇ -cyano- ⁇ -methyl-p- methoxycinnamate, butyl ⁇ -cyano- ⁇ -methyl-p-methoxy-cinnamate, methyl ⁇ - carbomethoxy-p-methoxycinnamate, N-( ⁇ -carbomethoxy- ⁇ -cyanovinyl)-2- methylindoline, ethyl-2-cyano-3,3-diphenylacrylate (UVINUL ® 3035); 2-ethylhexyl-2- cyano-3,3-diphenylacrylate (UVINUL ® 3039); 1 ,3-bis-[
  • this light stabilizer combination is used in an amount of 0.01 to 25 % by weight, based on the total weight of a light-stabilized composition.
  • the present invention is further illustrated by means of the following example.
  • MFI polypropylene
  • Irganox 101010 a phenolic antioxidant
  • Each composition is extruded through a flat nozzle to obtain a film with a thickness adjusted to the requirements of the accelerated weathering test according to ASTM D-5208. Examples of each film are exposed to such wheathering test.
  • the light stability of the sample is assessed by measuring the extent of carbonyl oxidation of the polymer by means of infrared spectroscopy. The measurement is carried out after 1000 hours exposition to accelerated weathering (UV-

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The present invention relates to a light-stabilized composition comprising at least one polymer and 0.01 to 25 % by weight, based on the total weight of the composition, of a light-stabilizing component comprising at least one heptaazaphenalene compound of general formula (I), wherein the radicals R1, R2 and R3 are defined in the description, optionally in combination with at least one further light stabilizer (Z), articles, moulds, sheets, foils or films produced of such light-stabilized composition, the use of at least one heptaazaphenalene compound of general formula (I) as a light stabilizer for polymers as well as to a light stabilizer combination comprising at least one of said heptaazaphenalene and at least one further light-stabilizer (Z).

Description

Light-stabilized composition
The present invention relates to a light-stabilized composition comprising at least one polymer and 0.01 to 25 % by weight, based on the total weight of the composition, of a light-stabilizing component comprising at least one heptaazaphenalene compound of general formula (I),
Figure imgf000002_0001
(D
wherein the radicals R1, R2 and R3 are defined in the description, optionally in combination with at least one further light stabilizer (Z), to articles, moulds, sheets, foils or films produced of such light-stabilized composition, to the use of at least one heptaazaphenalene compound of general formula (I) as a light stabilizer for polymers as well as to a light stabilizer combination comprising at least one of said heptaazaphenalene and at least one further light-stabilizer (Z).
Polymer compositions of various kinds are useful materials for many applications and are used in various industries as raw material for the production of various items such as for example articles or moulds of different size and shape, sheets, films, foils, paintings, coatings, as part of an end product or as end product for the consumer. Polymer compositions with high quality are replacing other materials such as glass, metal, paper and wood in an increasing extent. However, polymer compositions or articles thereof can be subject to rapid and severe degradation/deterioration because of exposure to light, impairing the mechanical properties like impact strength, flexibility or elasticity and causing discoloration, surface cracking or loss of gloss.
Despite the great diversity of already commercially available light stabilizers for polymers, there still exists a need for light stabilizers, which provide sufficient protection of a polymer composition against the deteriorating effect of light, especially in view of the global climate changes, which lead to an increase of sun light reaching the earth surface. Consequently, there is a need for an efficient protection of polymer compositions and items thereof against such increased exposure to sunlight and risk of light-induced degradation/decomposition.
Thus, it was an object of the present invention to provide polymer compositions, which are light stabilized, which means effectively protected against harmful degradation or decomposition caused/induced by light, such as e.g. UV light, sunlight or fluorescent indoor light.
This object was solved by the provision of the inventive light-stabilized composition comprising
at least one polymer and
0.01 to 25 % by weight, based on the total weight of the composition, of a light- stabilizing component comprising at least one heptaazaphenalene compound of general formula (I),
Figure imgf000003_0001
(I) wherein
the radicals Ri, R2 and R3 are defined hereinafter.
Such inventive, light-stabilized compositions show an effective protection against deteriorating effects resulting from light exposure, preferably UV light.
Thus, one aspect of the present invention is a light-stabilized composition comprising at least one polymer and 0.01 to 25 % by weight, based on the total weight of the composition, of a light-stabilizing component comprising at least one heptaazaphenalene compound of general formula (I),
Figure imgf000004_0001
(I) wherein
Ri, R2 and R3, independent of each other, each represents an unsubstituted or at least mono-substituted mono- or polycyclic aryl radical; an unsubstituted or at least mono-substituted, saturated, unsaturated or aromatic heterocyclic radical having from 5 to 10 atoms that can contain 1 , 2 or 3 heteroatoms independently selected from O, N and S; an -OR4 radical; or a -NR5R6 radical;
R4 represents a hydrogen atom; an unsubstituted or at least mono-substituted, saturated or unsaturated, linear or branched CMS aliphatic radical; an unsubstituted or at least mono-substituted 03-12 cycloalkyl radical; an unsubstituted or at least mono-substituted mono- or polycyclic aryl radical; an unsubstituted or at least mono- substituted, saturated, unsaturated or aromatic heterocyclic radical having from 5 to 14 atoms that can contain 1 , 2 or 3 heteroatoms independently selected from O, N and S; R5 and R6, independent of each other, each represents a hydrogen atom; an unsubstituted or at least mono-substituted, saturated or unsaturated, linear or branched CMS aliphatic radical; an unsubstituted or at least mono-substituted C3--I2 cycloalkyl radical; an unsubstituted or at least mono-substituted mono- or polycyclic aryl radical; an unsubstituted or at least mono-substituted, saturated, unsaturated or aromatic heterocyclic radical having from 5 to 10 atoms that can contain 1 , 2 or 3 heteroatoms independently selected from O, N and S;
or
R5 and Re form together with the bridging nitrogen atom an unsubstituted or at least mono-substituted saturated, unsaturated or aromatic mono- or polycyclic ring system having from 4 to 10 atoms that contains optionally 1 or 2 heteroatoms independently selected from N, O and S;
with the proviso that if each of the radicals Ri, R2 and R3 represent a -NR5R6 radical at the same time and R5 and Re, are identical, then R5 and Re shall not represent a hydrogen atom;
preferably with the proviso that if the radicals R-i, R2 and R3 are identical, R1, R2 and R3 shall at the same time not represent an unsubstituted phenyl radical;
preferably with the proviso that if each of the radicals Ri, R2 and R3 represent an
- OR4 radical at the same time, R4 shall not represent a hydrogen atom or a radical selected from the group consisting of n-butyl, ethyl, phenyl, benzyl, 2,6- dimethylphenyl, 3,5-dimethylphenyl, 2,2,3,3,4,4,4-heptafluorobutyl, 2,2,3,3,3- pentafluoropropyl, 2,2,2-trifluoroethyl and hydroxymethyl;
preferably with the proviso that if each of the radicals Ri, R2 and R3 represent an
- OR4 radical at the same time, and if R4 represents an ethyl radical for two of the radicals Ri, R2 and R3, then R4 shall not represent a hydrogen atom for the remaining third radical of the radicals Ri, R2 and R3; preferably with the proviso that if each of the radicals R1, R2 and R3 represent a
- NR5R6 radical at the same time, and R5 and R6, are identical, then R5 and R6 shall not represent a radical selected from the group consisting of ethyl, n-butyl, benzyl, n- heptyl, unsubstituted phenyl, cyclohexyl, 2-pyridyl and hydroxymethyl;
preferably with the proviso that if each of the radicals R-i, R2 and R3 represent a
- NR5R6 radical at the same time and if either R5 or R6 represents a hydrogen atom, then the other one of the radicals R5 and R6 shall not represent a radical selected from the group consisting of n-butyl, unsubstituted phenyl, hydroxymethyl, 4- methoxy-9,10-dihydro-9,10-dioxoanthracene-1-yl, 9,10-dihydro-9,10- dioxoanthracene-1-yl, 9,10-dihydro-9,10-dioxoanthracene-2-yl and 5-benzoylamino- 9,10-dihydro-9,10-dioxoanthracene-1-yl;
preferably with the proviso that if each of the radicals Ri, R2 and R3 represent a
- NR5R6 radical at the same time and if either R5 and R6 represents a phenyl radical, then the other one of the radicals R5 and R6 shall not represent a methyl radical;
preferably with the proviso that if each of the radicals R1, R2 and R3 each represents a -NR5R6 radical at the same time, and if each of the radicals R5 and R6 represent at the same time a n-heptyl radical for two of the radicals Ri, R2, and R3, then each of the radicals R5 and R6 of the third radical shall not represent a phenyl radical at the same time;
or
preferably with the proviso that if each of the radicals R1, R2 and R3 represent a - NR5R6 radical at the same time, and if each of the radicals R5 and R6 represent at the same time a phenyl radical for two of the radicals R1, R2 and R3, then each of the radicals R5 and R6 of the third radical shall not represent a n-heptyl radical at the same time.
and/or at least one of its stereoisomers, preferably enantiomers or diastereomers, a racemate or a mixture of at least two of its stereoisomers, preferably enantiomers and/or diastereomers in any mixing ratio, or at least one physiologically acceptable salt thereof, or at least one corresponding solvate thereof;
with the exception of a composition comprising 3% by weight of 2,5,8-tris-(4- (butoxycarbonyl)phenylamino)-1 ,3,4,6,7,9, 9b-heptaazaphenalene
Figure imgf000007_0001
5% by weight of ethylhexyl methoxycinnamate and 16% by weight of Arlamol HD ((Uniqema): Cyclomethicone, PPG-15, stearyl ether), based on the total weight of the composition, respectively;
with the exception of a composition comprising 6% by weight of 2-(4- (carboxy)phenylamino)-5,8-bis-(4-methylphenyl)-1 ,3, 4,6,7,9, 9b-heptaazaphenalene
Figure imgf000007_0002
2% by weight of PEG-100 Stearate (Simulsol M59 (Seppic)), 7.5% by weight of Propyleneglycol, Dicaprylate/dicaprate (Estol 1526 PDCC), 0.5% Dimethicone (SF 18-350 (General Electric)), 4% by weight of MT-T100 TV (Tayca: Titanium dioxide, aluminium hydroxide, stearic acid), 0.15% by weight of PNC 30 (sodium acrylates/cross-linked polymer, vinyl isodecanoate) and 1.5% by weight of butyleneglycol, based on the total weight of the composition, respectively;
and with the exception of a composition comprising 6% by weight of 2,5,8-tris-(4-(2- ethylhexyloxycarbonyl)phenylamino)-1 ,3, 4,6,7,9,9b-heptaazaphenalene
Figure imgf000008_0001
2% by weight of PEG-100 Stearate (Simulsol M59 (Seppic)), 7.5% by weight of Propyleneglycol, Dicaprylate/dicaprate (Estol 1526 PDCC), 0.5% Dimethicone (SF 18-350 (General Electric)), 4% by weight of MT-T100 TV (Tayca: Titanium dioxide, aluminium hydroxide, stearic acid), 0.15% by weight of PNC 30 (sodium acrylates/cross-linked polymer, vinyl isodecanoate) and 1.5% by weight of butyleneglycol, based on the total weight of the composition, respectively;
and
preferably with the exception of 62.5% by weight of 2,5,8-tris-(4- (butoxycarbonyl)phenylamino)-1 ,3,4,6,7,9, 9b-heptaazaphenalene
Figure imgf000008_0002
and 37.5% by weight of ethylhexyl methoxycinnamate, based on the weight of the combination of 2,5,8-tris-(4-(butoxycarbonyl)phenylamino)-1 ,3,4,6,7,9> 9b- heptaazaphenalene and ethylhexyl methoxycinnamate;
and/or
preferably with the exception of 60.5 - 67.6% by weight of 2-(4- (carboxy)phenylamino)-5,8-bis-(4-methylphenyl)-1 ,3, 4,6,7,9,9b-heptaazaphenalene
Figure imgf000009_0001
and 32.4 - 39.5% by weight of titanium dioxide, based on the weight of the combination of 2-(4-(carboxy)phenylamino)-5,8-bis-(4-methylphenyl)-1 ,3, 4,6,7,9,9b- heptaazaphenalene and titanium dioxide;
and/or
preferably with the exception of 60.5 - 67.6% by weight of 2,5,8-tris-(4-(2- ethylhexyloxycarbonyl)phenylamino)-1 ,3, 4,6,7, 9,9b-heptaazaphenalene
Figure imgf000010_0001
and 32.4 - 39.5% by weight of titanium dioxide, based on the weight of the combination of 2,5,8-tris-(4-(2-ethylhexyloxycarbonyl)phenylamino)-1 ,3, 4,6,7,9,9b- heptaazaphenalene and titanium dioxide.
The term "light stabilizer" (also referred to as "photostabilizer" or "photoprotecting agent") means, according to the present invention a chemical compound that protects the material like a polymer against photodegradation against deterioriating and/or decomposing effects caused by its exposure to light. With respect to the definition of "light stabilizer" reference is made to the International Union of Pure and Applied Chemistry (IUPAC) Definitions of terms relating to polymer chemistry, Pure and Appl. Chem., Vol. 68, No.12, pp. 2313-2323, 1996.
Preferably, light stabilizers can also be classified according to their special possibility of stabilizing against the impact of light into absorbers, quenchers, peroxide decomposers or free radical scavengers.
So called absorbers and quenchers are preferably agents that reduce the impact caused by exposure to light either by absorbing, extincting, filtering, scattering, deflecting or reflecting light, a peroxide decomposer is preferably an agent that transforms peroxides into stable compounds without the formation of free radicals and a free radical scavenger is preferably an agent that eliminates free radicals by binding. Preferably, the inventive light-stabilized composition comprises as the light-stabilizing component at least one absorber, quencher, peroxide decomposer and/or free radical scavenger.
In a preferred embodiment of the present invention the light-stabilizing component is at least one heptaazaphenalene compound of general formulae (IA) to (IL)
IT4 . R'3
Figure imgf000011_0001
Figure imgf000011_0002
NR 5R'6
Figure imgf000011_0003
R'eR'sN
Figure imgf000011_0004
NR5R6 IL
wherein R1, R'2 and R'3) independent of each other, each represents an unsubstituted or at least mono-substituted, mono- or polycyclic aryl radical; an unsubstituted or at least mono-substituted, saturated, unsaturated or aromatic heterocyclic radical having from 5 to 10 atoms that can contain 1 , 2 or 3 heteroatoms independently selected from O, N and S;
R4, R'4> Rπ 4 and Rm 4, independent of each other, each represents a hydrogen atom, an unsubstituted or at least mono-substituted, saturated or unsaturated linear or branched CMS aliphatic radical; an unsubstituted or at least mono-substituted 03.12 cycloalkyl radical; an unsubstituted or at least mono-substituted mono- or polycyclic aryl radical; an unsubstituted or at least mono-substituted saturated, unsaturated or aromatic heterocyclic radical having from 5 to 14 atoms that can contain 1 , 2 or 3 heteroatoms independently selected from O, N and S;
R'5, Rn5, Rm5, R'β. R"β and R'"6, independent of each other, each represents a hydrogen atom; an unsubstituted or at least mono-substituted, saturated or unsaturated, linear or branched CMS aliphatic radical; an unsubstituted or at least mono-substituted C3--I2 cycloalkyl radical; an unsubstituted or at least mono- substituted mono- or polycyclic aryl radical; an unsubstituted or at least mono- substituted saturated, unsaturated or aromatic heterocyclic radical having from 5 to 10 atoms that can contain 1 , 2 or 3 heteroatoms independently selected from O, N and S;
or
R'5, R"5, R'"5, R'β> R"β and R"'6, form together with the bridging nitrogen atom an unsubstituted or at least mono-substituted, saturated, unsaturated or aromatic mono- or polycyclic ring system which has 5 to 10 atoms as ring members and which contains optionally 1 , 2 or 3 heteroatoms independently selected from O, N and S;
preferably with the aforementioned provisos;
and/or at least one of its stereoisomers, preferably enantiomers or diastereomers, a racemate or a mixture of at least two of its stereoisomers, preferably enantiomers and/or diastereomers in any mixing ratio, or at least one physiologically acceptable salt thereof, or at least one corresponding solvate thereof.
According to a further preferred embodiment of the present invention, the light- stabilizing component is at least one heptaazaphenalene compound of general formula (IA)
Figure imgf000013_0001
(IA)
wherein
R'4> R"4 and R'"4, independent of each other, each represents an unsubstituted or at least mono-substituted, C3-i2 cycloalkyl radical; an unsubstituted or at least mono- substituted mono- or polycyclic aryl radical; an unsubstituted or at least mono- substituted saturated, unsaturated or aromatic heterocyclic radical having from 5 to 14 atoms that can contain 1 , 2 or 3 heteroatoms independently selected from O, N and S;
preferably with the aforementioned provisos; and preferably with the proviso that if R'4, R"4 and R'"4 are at the same time identical, they shall not represent phenyl, benzyl, 2,6-dimethylphenyl or 3,5-dimethylphenyl;
and/or at least one of its stereoisomers, preferably enantiomers or diastereomers, a racemate or a mixture of at least two of its stereoisomers, preferably enantiomers and/or diastereomers in any mixing ratio, or at least one physiologically acceptable salt thereof, or at least one corresponding solvate thereof. According to a further preferred embodiment of the present invention, the light- stabilizing component is at least one heptaazaphenalene compound as defined above,
wherein
R4, R!4. R"4 and R'"4, identical or different, each represents an unsubstituted or at least mono-substituted aryl group, wherein said substituent(s) are independently from each other selected from the group consisting of an unsubstituted or at least mono- substituted C3-12 cycloalkyl radical; an unsubstituted or at least mono-substituted C2-6 alkenyl radical; an unsubstituted or at least mono-substituted aryl radical; an unsubstituted or at least mono-substituted, saturated, unsaturated or aromatic heterocyclic radical having from 5 to 10 atoms that can contain 1 , 2 or 3 heteroatoms independently selected from O, N and S; a -C(=O)-OR7 radical; a -C(=O)NR8R9 radical; a -CORi0 radical; an -OH radical; F, Cl, Br or I; an unsubstituted or at least mono-substituted, linear or branched -0-C1-8 radical; an unsubstituted or at least mono-substituted, linear or branched Ci-6 alkyl radical, wherein the substituent(s) for the aforementioned -0-Ci-8 radical and/or the aforementioned d-β alkyl radical represent, independently from each other, an -OH radical; a -SO3M radical; a - N(Rn)2 radical; a -N(Rn)3 + radical or a moiety of general formula (II):
Figure imgf000014_0001
(H)
wherein
m= 0 or 1 ; P= O, 1 , 2, 3 or 4
R12. Ri3, R14, R15 and Ri6, identical or different, each represents an unsubstituted or at least mono-substituted, linear or branched Ci_6 alkyl radical; an unsubstituted or at least mono-substituted, linear or branched -O-Ci-6 radical; an unsubstituted or at least mono-substituted aryl radical or an -OSi(Ri7)3 radical;
R17 represents an unsubstituted or at least mono-substituted, linear or branched Ci-6 alkyl radical, an unsubstituted or at least mono-substituted, linear or branched -0-Ci-8 radical or an unsubstituted or at least mono-substituted aryl radical;
M represents H, Na+ or K+;
R7, R8 and R9 , independent from each other, each represents a hydrogen atom; an unsubstituted or at least mono-substituted aryl radical; an unsubstituted or at least mono-substituted, linear or branched CMS alkyl radical; an unsubstituted or at least mono-substituted, C3-i2 cycloalkyl radical; an unsubstituted or at least mono- substituted saturated, unsaturated or aromatic heterocyclic radical having from 5 to 10 atoms that can contain 1 , 2 or 3 heteroatoms independently selected from O, N and S;
or
R8 and Rg form together with the bridging nitrogen atom an unsubstituted or at least mono-substituted, saturated, unsaturated or aromatic mono- or polycyclic ring system having from 5 to 10 atoms as ring members that contains optionally 1 or 2 heteroatoms independently selected from O, N and S;
R-io represents an unsubstituted or at least mono-substituted, linear or branched alkyl radical, or an unsubstituted or at least mono-substituted aryl radical,
or
Rio is fused to form a mono- or polycyclic saturated, unsaturated or aromatic ring system having from 5 to 10 atoms as ring members that contains optionally 1 or 2 heteroatoms independently selected from O, N and S; R11 represents an unsubstituted or at least mono-substituted, linear or branched alkyl radical;
preferably with the aforementioned provisos;
and/or at least one of its stereoisomers, preferably enantiomers or diastereomers, a racemate or a mixture of at least two of its stereoisomers, preferably enantiomers and/or diastereomers in any mixing ratio, or at least one physiologically acceptable salt thereof, or at least one corresponding solvate thereof.
According to a further preferred embodiment of the present invention, the light- stabilizing component is at least one heptaazaphenalene compound of general formula (IB)
Figure imgf000016_0001
M
R'βR'sN NDFr"'5 DFT"1 6
(IB)
wherein
the radicals within each radical pair R'5 R'6, R"s R"6, and R'"5Rm6, different from each other, each represents a hydrogen atom; an unsubstituted or at least mono- substituted, linear or branched Ci-is alkyl radical; an unsubstituted or at least mono- substituted C3-12 cycloalkyl radical; an unsubstituted or at least mono-substituted mono- or polycyclic aryl radical; an unsubstituted or at least mono-substituted, saturated, unsaturated or aromatic heterocyclic radical having from 5 to 10 atoms that can contain 1 , 2 or 3 heteroatoms independently selected from O, N and S;
or the radical pairs R'5 R'6l R"s R"6, or R'"5R'"6 form together with the bridging nitrogen atom an unsubstituted or at least mono-substituted, saturated, unsaturated or aromatic mono- or polycyclic ring system having from 4 to 10 atoms as ring members that contains optionally 1 or 2 heteroatoms selected from N, O and S;
preferably with the proviso that if one of the radicals within each radical pair R'5 R'6) Rn 5 R"6. and R'"5R'"6 is hydrogen, the other radical is different from n-butyl, phenyl, hydroxymethyl, 4-methoxy-9,10-dihydro-9,10-dioxoanthracene-1-yl, 9,10-dihydro- 9,10-dioxoanthracene-1-yl, 9,10-dihydro-9,10-dioxoanthracene-2-yl, or 5- benzoylamino-9,10-dihydro-9,10-dioxoanthracene-1-yl;
and
preferably with the aforementioned provisos;
and
preferably with the proviso that if one of the radicals of each of the radical pairs R'5 R'β, Rn 5 R"6> and R'^R"^ is phenyl, the other radical shall not represent a methyl radical;
and/or at least one of its stereoisomers, preferably enantiomers or diastereomers, a racemate or a mixture of at least two of its stereoisomers, preferably enantiomers and/or diastereomers in any mixing ratio, or at least one physiologically acceptable salt thereof, or at least one corresponding solvate thereof.
According to a further preferred embodiment of the present invention, the light- stabilizing component is at least one heptaazaphenalene compound as defined above,
wherein one radical of the pair R5R6 or optionally one radical of the pairs R'sR'β, R"5R"6 or R'"5R'"6 represents an unsubstituted or at least mono-substituted aryl radical, wherein said substituent(s) are, independently from each other, selected from the group consisting of an unsubstituted or at least mono-substituted, 03.12 cycloalkyl radical; a linear or branched, unsubstituted or at least mono-substituted C2-6 alkenyl radical; an unsubstituted or at least mono-substituted aryl radical; an unsubstituted or at least mono-substituted saturated, unsaturated or aromatic heterocyclic radical having from 5 to 10 atoms that can contain 1 , 2 or 3 heteroatoms independently selected from O1 N and S; a -C(=O)-OR7 radical; a -C(=O)NR8Rg radical; a -CORi0 radical; -OH; F, Cl, Br, I; an unsubstituted or at least mono-substituted, linear or branched -O-C1.8 radical; an unsubstituted or at least mono-substituted, linear or branched Ci-6 alkyl radical, wherein the substituent(s) for the aforementioned -O-Ci-β radical and/or the aforementioned Ci-6 alkyl radical represent(s) independently from each other at least one -SO3M radical, a -N(Rn)2 radical, a -N(Rn)3 + radical, or a moiety of general formula (II)
Figure imgf000018_0001
(II)
wherein
m= O or 1 ; P= O, 1 , 2, 3 or 4;
Ri2, R13, Ri4, R15 and R16, identical or different, each represents an unsubstituted or at least mono-substituted, linear or branched Ci-6 alkyl radical; an unsubstituted or at least mono-substituted, linear or branched -O-Ci-β radical; an unsubstituted or at least mono-substituted aryl radical or an -OSi(Ri7)3 radical; Ri7 represents an unsubstituted or at least mono-substituted, linear or branched Cvβ alkyl radical; an unsubstituted or at least mono-substituted, linear or branched -0-Ci-6 radical or an unsubstituted or at least mono-substituted aryl radical;
M represents H, Na+ or K+;
R7, Re and Rg, identical or different, each represents a hydrogen atom; an unsubstituted or at least mono-substituted aryl radical; an unsubstituted or at least mono-substituted, linear or branched C-MS alkyl radical; an unsubstituted or at least mono-substituted, 03.12 cycloalkyl radical or an unsubstituted or at least mono- substituted saturated, unsaturated or aromatic heterocyclic having from 5 to 10 atoms that can contain 1 , 2 or 3 heteroatoms independently selected from O, N and S;
or
R8 and R9 form together with the bridging nitrogen atom an unsubstituted or at least mono-substituted, saturated, unsaturated or aromatic mono- or polycyclic ring system having from 5 to 10 atoms that contains optionally 1 or 2 heteroatoms independently selected from O, N and S;
R10 represents an unsubstituted or at least mono-substituted, saturated or unsaturated, linear or branched C1^ alkyl radical or an unsubstituted or at least mono-substituted aryl radical;
or
R10 is fused to form a mono- or polycyclic saturated, unsaturated or aromatic ring system having from 5 to 10 atoms that contains optionally 1 or 2 heteroatoms independently selected from O, N and S;
R11 represents an unsubstituted or at least mono-substituted, linear or branched alkyl radical; preferably with the proviso that if one radical of the pair R5Rβ or optionally one radical of the pairs R'sR'e. R"5R"6 or R"'5R'"6 represents an unsubstituted phenyl, 4- methoxy-9,10-dihydro-9,10-dioxoanthracene-1-yl, 9,10-dihydro-9,10- dioxoanthracene-1-yl, 9,10-dihydro-9,10-dioxoanthracene-2-yl, or 5-benzoylamino- 9,10-dihydro-9,10-dioxoanthracene-1-yl radical, the other radical is different from hydrogen;
preferably with the aforementioned provisos;
and/or at least one of its stereoisomers, preferably enantiomers or diastereomers, a racemate or a mixture of at least two of its stereoisomers, preferably enantiomers and/or diastereomers in any mixing ratio, or at least one physiologically acceptable salt thereof, or at least one corresponding solvate thereof.
According to a further preferred embodiment of the present invention, the light- stabilizing component is at least one heptaazaphenalene compound of general formula (IC)
Figure imgf000020_0001
(IC)
wherein
R'T , R'2 and R'3, identical or different, each represents an unsubstituted or at least mono-substituted mono- or polycyclic aryl radical; an unsubstituted or at least mono- substituted saturated, unsaturated or aromatic heterocyclic radical having from 5 to 10 atoms that can contain 1 , 2 or 3 heteroatoms independently selected from O, N and S; preferably with the aforementioned provisos;
and
preferably with the proviso that R'i, Rn 2 and R'"3 shall not at the same time represent a phenyl, methylphenyl, dimethylphenyl, trimethylphenyl, and 2,3,5,6- tetramethylphenyl;
and/or at least one of its stereoisomers, preferably enantiomers or diastereomers, a racemate or a mixture of at least two of its stereoisomers, preferably enantiomers and/or diastereomers in any mixing ratio, or at least one physiologically acceptable salt thereof, or at least one corresponding solvate thereof.
According to a further preferred embodiment of the present invention, the light- stabilizing component is at least one heptaazaphenalene compound as defined above,
wherein
R-I, R2 and R3, or R'i, R'2 and R'3, identical or different, each represents at least one radial selected from the group consisting of naphthyl, pyrrole, thiophene, indole, pyrazole, imidazole, triazole, benzothiophene, benzimidazole, benzopyrazole, oxazole, isoxazole, benzofurane, which is unsubstituted or at least mono-substituted;
or
represents a radical of general formula (III)
Figure imgf000022_0001
wherein
Ri8 represents a hydrogen atom; -OH; an -OR22 radical; an unsubstituted or at least mono-substituted, saturated or unsaturated, linear or branched C-M8 alkyl radical; or an unsubstituted or at least mono-substituted, linear or branched -0-Ci-Is radical;
R19 represents a hydrogen atom; -OH; an unsubstituted or at least mono-substituted aryl radical; an unsubstituted or at least mono-substituted saturated, unsaturated or aromatic heterocyclic radical having from 5 to 10 atoms that can contain 1 , 2 or 3 heteroatoms independently selected from O, N and S; a -C(=O)-OR7 radical; a - C(=O)NRβR9 radical; an -OR22 radical; an unsubstituted or at least mono-substituted -COR10 radical; an unsubstituted or at least mono-substituted, C3_6 cycloalkyl radical; a saturated or unsaturated, linear or branched CMS alkyl radical, which is unsubstituted or at least mono-substituted by at least one hydroxyl radical; a -SO3M radical; a -N(Rn)2 radical; a -N(R11J3 + radical, or by a group of general formula (II)
Figure imgf000022_0002
(M) wherein
m= O or 1 ; P= O, 1 , 2, 3 or 4; Ri2. Ri3> Ri4, Ri5 and Ri6, identical or different, each represents an unsubstituted or at least mono-substituted, linear or branched CMS alkyl radical; an unsubstituted or at least mono-substituted, linear or branched -O-C-ι-6 radical; an unsubstituted or at least mono-substituted aryl radical or an -OSi(Ri7)3 radical;
Ru represents an unsubstituted or at least mono-substituted, linear or branched C-ι-6 alkyl radical; an unsubstituted or at least mono-substituted, linear or branched -O-Ci-6 radical or an unsubstituted or an at least mono-substituted aryl radical;
M represents H, Na+ or K+;
R7, Re and Rg, identical or different, each represents a hydrogen atom; an unsubstituted or at least mono-substituted aryl radical; an unsubstituted or at least mono-substituted, linear or branched CMS alkyl radical; an unsubstituted or at least mono-substituted, C3-C12 cycloalkyl radical or an unsubstituted or at least mono- substituted saturated, unsaturated or aromatic heterocyclic radical having from 5 to 10 atoms that can contain 1 , 2 or 3 heteroatoms independently selected from O, N and S;
or
Re and Rg form together with the bridging nitrogen atom a saturated, unsaturated or aromatic mono- or polycyclic ring system having from 5 to 10 atoms as ring members that contains optionally 1 or 2 heteroatoms independently selected from O, N and S;
R10 represents an unsubstituted or at least mono-substituted saturated or unsaturated, linear or branched Ci-6 alkyl radical, or an unsubstituted or at least mono-substituted aryl radical,
or
R10 is fused to form an unsubstituted or at least mono-substituted, saturated, unsaturated or aromatic mono- or polycyclic ring system having from 5 to 10 atoms as ring members that contains optionally 1 or 2 heteroatoms independently selected from O, N and S;
Rn represents an unsubstituted or at least mono-substituted, linear or branched alkyl radical;
R22 represents an unsubstituted or at least mono-substituted aryl radical; an unsubstituted or at least mono-substituted saturated, unsaturated or aromatic heterocyclic radical having from 5 to 10 atoms that can contain 1 , 2 or 3 heteroatoms independently selected from O, N and S; an unsubstituted or at least mono- substituted -COR10 radical; an unsubstituted or at least mono-substituted 03.12 cycloalkyl radical; a saturated or unsaturated linear or branched Ci--I8 alkyl radical which is unsubstituted or at least mono-substituted by at least one -OH radical; a - SO3M radical; a -N(Rn)2 radical; a -N(Rn)3 + radical or by a radical of general formula (II)
Figure imgf000024_0001
(N) wherein
m= O or 1 ; p= 0, 1 , 2, 3 or 4
and wherein
R7, Re. RΘ> Rio, Ri 1. R12, Ri3, Ri4, Ri5, R16 and M have the above defined meaning;
R20 and R21, identical or different, each represents a hydrogen atom; an unsubstituted or at least mono-substituted, saturated or unsaturated, linear or branched d-6 alkyl radical; an unsubstituted or at least mono-substituted, linear or branched -0-Cr6 radical or a -SO3M radical, with M being H, Na+ or K+;
preferably with the aforementioned provisos;
and/or at least one of its stereoisomers, preferably enantiomers or diastereomers, a racemate or a mixture of at least two of its stereoisomers, preferably enantiomers and/or diastereomers in any mixing ratio, or at least one physiologically acceptable salt thereof, or at least one corresponding solvate thereof.
According to a further preferred embodiment of the present invention, the light- stabilizing component is at least one heptaazaphenalene compound as defined above,
wherein
R4 represents a radical selected from the group consisting of 4-methoxyphenyl, naphthyl, cyclopentyl and cyclohexyl;
R5, R'5. RM5, R'"5, Rβ> R'e, R"e and R"6 are different from each other and each represent a hydrogen atom, cyclopropyl, cyclohexyl, cyclobutyl, cycloheptyl, cyclopentyl, 4-(hydroxycarbonyl)phenyl, 4-(butoxycarbonyl)phenyl, 4-(2- ethylhexyloxycarbonyl)phenyl, 4-(2-butyloctyloxycarbonyl)phenyl, 4-(2- hexyldecyloxycarbonyl)phenyl, 4-(3,3,5-trimethylcyclohexyloxycarbonyl)phenyl, 4- (3,3,5-trimethylhexyloxycarbonyl)phenyl, 4-(octadecyloxycarbonyl)phenyl, 4- (hexadecyloxycarbonyl)phenyl, 4-(docecyloxycarbonyl)phenyl, 4-((2- ethylhexyl)carbamoyl)phenyl, 4-(l_-menthyloxycarbonyl)phenyl, 4-styrylphenyl, 3- styrylphenyl, 3-((E)-3-(2-ethylhexyloxy)-3-oxoprop-1 -enyl)phenyl, 4-((E)-3-(2- ethylhexyloxy)-3-oxoprop-1-enyl)phenyl, 4-methoxyphenyl, 3-methoxyphenyl, 3- nitrophenyl, phenyl, biphenyl-4-yl, 4-(imidazo[1 ,2-a]pyridin-2-yl)phenyl, 4-(4,5,6,7- tetrahydro-2,6,6-trimethyl-4-oxoindol-1 -yl)phenyl, 4-(1 H-benzo[d]imidazol-2-yl)phenyl, hydroxymethyl, pyridin, heptyl, butyl, ethyl, 2-ethylhexyl, 4-(1 ,3,3-trimethylbicy- clo[2.2.1]heptan-2-yloxy)phenyl, 1 H-indol-5-yl, 4-((3,7-dimethylocty- loxy)carbonyl)phenyl, 2-amino-4,5-dimethylphenyl or n-propyl;
R7 represents a hydrogen atom, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, n-pentyl, n-hexyl, 2-ethylhexyl, L-menthyl, 3,3,5-trimethylcyclohexanyl, 3,3,5- trimethylhexanyl, dodecyl, 2-butyloctyl, 2-hexyldecyl, hexadecyl, octadecyl, 3,7- dimethyloctyl , 1 ,3,3-trimethylbicyclo[2.2.1]heptan-2-yl, unsubstituted or at least mono-substituted benzyl radical or an unsubstituted or at least mono-substituted phenyl radical;
Re and Rg, identical or different, each represents a hydrogen atom, methyl, ethyl, n- propyl, isopropyl, n-butyl, tert-butyl, n-pentyl, n-hexyl, 2-ethylhexyl, L-menthyl, 3,3,5- trimethylcyclohexanyl, 3,3,5-trimethylhexanyl, dodecyl, hexadecyl, 2-butyloctyl, 2- hexyldecyl, octadecyl, 3,7-dimethyloctyl, 1 ,3,3-trimethylbicyclo[2.2.1]heptan-2-yl, unsubstituted or at least mono-substituted benzyl radical or an unsubstituted or at least mono-substituted phenyl radical;
Rio represents methyl, ethyl, n-propyl, n-butyl, tert-butyl or phenyl;
Ri2, Ri3. Ri4> Ri5 and Riβ, independent of each other, each represents methyl, ethyl, -0-CH3, -0-CH2-CH3 or phenyl;
Ri7 represents methyl, ethyl, -O-CH3, -0-CH2-CH3 or phenyl;
Ri8 represents a hydrogen atom, -OH, methyl, -0-CH3, -0(C=O)-CH3, -0(C=O)-CH2- CH3, or -0(C=O)-CH2-CH2-CH3;
R19 represents a hydrogen atom, -OH, -0(C=O)-CH3, -0(C=O)-CH2-CH3, -0(C=O)- CH2-CH2-CH3, -0-CH3, a saturated or unsaturated, linear or branched -0-CH3, -O- CH2-CH3, -0-CH2-CH2-CH3, -0-CH2-CH2-CH2-CH3, -O-phenyl or a 2-ethylhexyloxy radical which is unsubstituted or at least mono-substituted with a -SO3M or a - N(Rn)3 + radical, with M being H1 K+ or Na+; R2O and R2i, identical or different, each represents a hydrogen atom, -OH, -0-CH3, - 0-CH2-CH3, -0-CH2-CH2-CH3, -0-CH2-CH2-CH2-CH3, -O-phenyl or a 2-ethylhexyloxy radical which is unsubstituted or at least mono-substituted with at least one -SO3M group, with M being H, K+ or Na+;
preferably with the aforementioned provisos;
and/or at least one of its stereoisomers, preferably enantiomers or diastereomers, a racemate or a mixture of at least two of its stereoisomers, preferably enantiomers and/or diastereomers in any mixing ratio, or at least one physiologically acceptable salt thereof, or at least one corresponding solvate thereof.
According to a further preferred embodiment of the present invention, the light- stabilizing component is at least one heptaazaphenalene compound of general formula (YA)
Figure imgf000027_0001
wherein
R22, R23> R24, R25. R26, R27> R28> R29, R30 and R3i have the following meaning:
Figure imgf000027_0002
Figure imgf000028_0001
Figure imgf000029_0001
Figure imgf000030_0001
Figure imgf000031_0001
Figure imgf000032_0002
-Ph stands for a phenyl radical, -O-But** stand for an -O-butyl radical and -O-Ac stand for an -0-acyl radical;
preferably with the aforementioned provisos;
and/or at least one of its stereoisomers, preferably enantiomers or diastereomers, a racemate or a mixture of at least two of its stereoisomers, preferably enantiomers and/or diastereomers in any mixing ratio, or at least one physiologically acceptable salt thereof, or at least one corresponding solvate thereof.
According to a further preferred embodiment of the present invention, the light- stabilizing component is at least one heptaazaphenalene compound of general formula (YB)
Figure imgf000032_0001
(YB), wherein
R32 represents a radical selected from the group consisting of
Figure imgf000033_0001
preferably with the aforementioned provisos;
and/or at least one of its stereoisomers, preferably enantiomers or diastereomers, a racemate or a mixture of at least two of its stereoisomers, preferably enantiomers and/or diastereomers in any mixing ratio, or at least one physiologically acceptable salt thereof, or at least one corresponding solvate thereof.
According to a further preferred embodiment of the present invention, the light- stabilizing component is at least one heptaazaphenalene compound of general formula (YC)
Figure imgf000033_0002
wherein R33, R34 and R35 have the following meaning:
Figure imgf000033_0003
preferably with the aforementioned provisos;
and/or at least one of its stereoisomers, preferably enantiomers or diastereomers, a racemate or a mixture of at least two of its stereoisomers, preferably enantiomers and/or diastereomers in any mixing ratio, or at least one physiologically acceptable salt thereof, or at least one corresponding solvate thereof.
According to a further preferred embodiment of the present invention, the light- stabilizing component is at least one heptaazaphenalene compound of general formula (YD)
Figure imgf000034_0001
(YD), wherein
R36 and R37 have the following meaning:
Figure imgf000034_0002
preferably with the aforementioned provisos; and/or at least one of its stereoisomers, preferably enantiomers or diastereomers, a racemate or a mixture of at least two of its stereoisomers, preferably enantiomers and/or diastereomers in any mixing ratio, or at least one physiologically acceptable salt thereof, or at least one corresponding solvate thereof.
According to a further preferred embodiment of the present invention, the light- stabilizing component is a heptaazaphenalene compound of formula (YE)
Figure imgf000035_0001
(YE),
preferably with the aforementioned provisos;
and/or at least one of its stereoisomers, preferably enantiomers or diastereomers, a racemate or a mixture of at least two of its stereoisomers, preferably enantiomers and/or diastereomers in any mixing ratio, or at least one physiologically acceptable salt thereof, or at least one corresponding solvate thereof.
According to a further preferred embodiment of the present invention, the light-stabilizing component is at least one heptaazaphenalene compound of general formula (YF)
Figure imgf000036_0001
(YF), wherein
R38> R39. R401 R41, R42 and R43 have the following meaning:
Figure imgf000036_0002
-Ph stands for a phenyl radical, -CH2-Ph** stand for a -CH2-phenyl radical;
preferably with the aforementioned provisos;
and/or at least one of its stereoisomers, preferably enantiomers or diastereomers, a racemate or a mixture of at least two of its stereoisomers, preferably enantiomers and/or diastereomers in any mixing ratio, or at least one physiologically acceptable salt thereof, or at least one corresponding solvate thereof. According to a further preferred embodiment of the present invention, the light- stabilizing component is at least one heptaazaphenalene compound of general formula (YG)
Figure imgf000037_0001
(YG), wherein
R44, R45 and R46 have the following meaning:
Figure imgf000037_0002
Figure imgf000038_0001
-Ph* stand for a phenyl radical and C-O-Ph** stands for a -C-O-phenyl radical;
preferably with the aforementioned provisos;
and/or at least one of its stereoisomers, preferably enantiomers or diastereomers, a racemate or a mixture of at least two of its stereoisomers, preferably enantiomers and/or diastereomers in any mixing ratio, or at least one physiologically acceptable salt thereof, or at least one corresponding solvate thereof.
According to a further preferred embodiment of the present invention, the light- stabilizing component is at least one heptaazaphenalene compound selected from the group comprising • 2,5,8-tris-(4-(butoxycarbonyl)phenylamino)-1 ,3,4,6,7,9, 9b-heptaazaphenalene,
• 2,5,8-tris-(4-(2-ethylhexyloxycarbonyl)phenylamino)-1 ,3, 4,6,7,9,9b- heptaazaphenalene,
• 2,5,8-tris-(4-(imidazo[1 ,2-a]pyridin-2-yl)-phenylamino) -1 ,3,4,6,7,9,9b- heptaazaphenalene,
• 2,5,8-tris-(4-(4,5,6,7-tetrahydro-2,6,6-trimethyl-4-oxo indol-1 -yl)phenylamine)- 1 ,3,4,6,7,9,9b-heptaazaphenalene,
• 2,5,8-tris-(biphenyl-4-ylamino)-1 ,3,4,6,7,9,9b-heptaaza phenalene,
• 2,5,8-tris-(4-(1 H-benzo[d]imidazol-2-yl)phenylamino)-1 , 3,4,6,7,9,9b- heptaazaphenalene,
• 2,5-bis-(biphenyl-4-ylamino)-8-(4-(butoxycarbonyl)phe nylamino)-1 ,3,4,6,7,9,9b- heptaazaphenalene,
• 2-(biphenyl-4-ylamino)-5-(4-(butoxycarbonyl)phenylami no)-8-(4-(2- ethylhexyloxycarbonyl)phenylamino)-1 ,3,4, 6,7,9,9b-heptaazaphenalene,
• 2,5,8-tris-(2,4-dihydroxyphenyl)-1 ,3,4,6,7,9,9b-heptaaza phenalene,
• 2, 5-dichloro-8-(1-methyl-1 H-pyrrol-2-yl)-1 , 3,4,6,7,9, 9b-heptaazaphenalene,
• 2, 5-bis-(4-(butoxycarbonyl)phenylamino)-8-(2-(1 -methyl-1 H-pyrrol-2-yl)- 1 ,3,4,6,7,9,9b-heptaazaphenalene,
• 2-(4-(carboxy)phenylamino)-5,8-bis-(4-methylphenyl)-1 ,3, 4,6,7,9,9b- heptaazaphenalene,
• 2,5,8-tris-(4-(4,5,6,7-tetrahydro-2,6,6-trimethyl-4-oxo indol-1 -yl)phenylamine)- 1 ,3,4,6,7,9,9b-heptaazaphenalene,
• 2,5-bis-(4-(butoxycarbonyl)phenylamino)-8-(1-methyl-1 H-pyrrol-2-yl)-1 ,3,4,6,7,9,9b- heptaazaphenalene,
• 2,5-bis(2,4-dihydroxyphenyl)-8-(1 -methyl-1 H-pyrazol-5-yl)-1 ,3,4,6,7,9,9b- heptaazaphenalene,
• 2, 5-bis{[4-(2-ethylhexyloxy)-2-hydroxy]phenyl}-6-(1 -methyl-1 H-pyrazol-5-yl)- 1 , 3,4,6,7,9, 9b-heptaazaphenalene,
• 2-[2,4-bis(2-ethylhexyloxy)phenyl]-5-[4-(2-ethylhexyl oxy)-2-hydroxyphenyl]-8-(1 - methyl-1 H-pyrazol-5-yl)-1 ,3, 4,6,7,9,9b-heptaazaphenalene,
• 2,5-bis(2,4-dihydroxyphenyl)-8-(1 -phenyl-1 H-pyrazol-5-yl)-1 ,3,4,6,7,9,9b- heptaazaphenalene,
• 2,5-bis{[4-(2-ethylhexyloxy)-2-hydroxy]phenyl}-8-(1 -phenyl-1 H-pyrazol-5-yl)- 1 ,3,4,6,7,9,9b-heptaazaphenalene,
• 2,5-bis[4-(butoxycarbonyl)phenylamino]-8-(1 -methyl-1 H-pyrazol-5-yl)-1 ,3,4,6,7,9,9b- heptaazaphenalene,
• 2, 5-bis{4-[(2-(ethylhexyloxy)carbonyl]phenylamino}-8-(1 -methyl-1 H-pyrazol-5-yl)- 1 ,3,4,6,7,9,9b-heptaazaphenalene,
• 2,5-bis[4-(butoxycarbonyl)phenylamino]-8-(1 -phenyl-1 H-pyrazol-5-yl)-1 , 3,4,6, 7,9, 9b- heptaazaphenalene,
• 2, 5-bis{4-[(2-ethylhexyloxy)carbonyl]phenylamino}-8-(1 -phenyl-1 H-pyrazol-5-yl)- 1 ,3,4,6,7,9,9b-heptaazaphenalene,
• 2-(1-benzyl-1 H-pyrrol-2-yl)-5,8-bis(2,4-dihydroxy phenyl)-1 ,3,4,6,7,9,9b- heptaazaphenalene,
• 2-(1-benzyl-1 H-pyrrol-2-yl)-5,8-bis[4-(2-ethylhexyloxy)-2-hydroxyphenyl]- 1 ,3,4,6,7,9,9b-heptaazaphenalene,
• 2-(1-benzyl-1 H-pyrrol-2-yl)-5,8-bis[4-(butoxycarbonyl) phenylamino]-1 ,3,4,6,7,9,9b- heptaazaphenalene,
• 2-(1-benzyl-1 H-pyrrol-2-yl)-5,8-bis(biphenyl-4-ylamino)-1 , 3,4,6,7,9,9b- heptaazaphenalene,
• 2-(1-benzyl-1 H-pyrrol-2-yl)-5,8-bis(4-benzoylphenylami-no)-1 ,3,4,6,7,9,9b- heptaazaphenalene,
• 2-(1-benzyl-1 H-pyrrol-2-yl)-5,8-bis(9-oxo-9H-fluoren-3-ylamino)-1 ,3,4,6,7,9,9b- heptaazaphenalene, • 2-(4-(tert-butylcarbamoyl)phenylamino)-5,8-bis-(4-(2- ethylhexyloxycarbonyl)phenylamino)-1 ,3,4,6,7,9,9b-heptaazaphenalene,
• 2, 5-bis-[(4-(2-ethylhexyloxy)-2-hydroxy)-phenyl]-8-(4-methoxyphenyl)-1 , 3,4,6, 7,9,9b- heptaazaphenalene,
• 2-(2-ethylhexylamino)-5,8-bis-(4-(5-(1 ,1-dimethylpropyl)benzo[d]oxazol-2- yl)phenylamino)-1 , 3,4,6,7,9, 9b-heptaazaphenalene,
• 2,5,8-tris-(4-(1 H-pyrazol-1-yl)phenylamino)-1 ,3,4,6, 7, 9,9b-heptaazaphenalene
• 2,5,8-tris-(4-benzoylphenylamino)-1 ,3,4,6,7,9,9b-hepta azaphenalene,
• 2,5,8-tris-(4-butoxy-2-hydroxyphenyl)-1 ,3,4,6,7,9,9b-heptaazaphenalene,
• 2,5,8-tris-(naphthalen-2-ylamino)-1 ,3,4,6,7,9,9b-hepta azaphenalene,
• 2,5-bis-(4-(butoxycarbonyl)phenylamino)-8-(2-(1-methyl-1 H-indol-3-yl)-1 ,3,4,6,7,9,9b- heptaazaphenalene,
• 2,5,8-tris-(biphenyl-4-yloxy)-1 ,3,4,6,7,9,9b-heptaaza phenalene,
• 2,5,8-tris-(3-methoxyphenylamino)-1 ,3,4,6,7,9,9b-hepta azaphenalene,
• 2,5,8-tris-(4-methoxyphenylamino)-1 ,3,4,6,7,9,9b-hepta azaphenalene,
• 2,5,8-tris-(4-((E)-3-ethoxy-3-oxoprop-1 -enyl)phenyl amino)-1 ,3,4,6,7,9,9b- heptaazaphenalene,
• 2,5,8-tris-(methoxycarbonyl-4'-biphenyl-4-ylamino)-1 ,3, 4,6,7,9,9b- heptaazaphenalene,
• 2,5,8-tris-(4-(methoxycarbonyl)phenylamino)-1 ,3,4,6, 7,9,9b-heptaazaphenalene,
• 2,5,8-tris-(4-(1 H-benzo[d]imidazol-2-yl)-3-hydroxy phenylamino)-1 ,3,4,6,7,9,9b- heptaazaphenalene,
• 2,5,8-tris-(4-(phenylamino)phenylamino)-1 ,3,4,6,7,9,9b-heptaazaphenalene,
• 2,5,8-tris-((4-(E)-styrylphenyl)amino)-1 ,3,4,6,7,9,9b-heptaazaphenalene,
• 2,5,8-tris-(2-ethylhexylamino)-1 ,3,4,6,7,9,9b-heptaaza phenalene,
• 2,5,8-tris-(4-(L-menthylcarbonyl)phenylamino)-1 ,3,4,6, 7,9,9b-heptaazaphenalene,
• 2,5,8-tris-(4-((3,3,5-trimethylcyclohexyloxy)carbonyl) phenylamino)-1 ,3,4,6,7,9,9b- heptaazaphenalene,
• 2,5,8-tris-(4-((E)-3-(2-ethylhexyloxy)-3-oxoprop-1-enyl) phenylamino)-1 ,3,4,6,7,9,9b- heptaazaphenalene,
• 2-(3-((E)-3-(2-ethylhexyloxy)-3-oxoprop-1 -enyl)phenyl amino)-5,8-bis-(4-((E)-3-(2- ethylhexyloxy)-3-oxoprop-1-enyl)phenylamino)-1 ,3,4,6,7,9,9b-heptaazaphenalene,
• 2,5,8-tris-(3-nitrophenylamino)-1 ,3,4,6,7,9,9b-heptaaza phenalene,
• 2,5,8-tris-(4-(2-butyloctyloxycarbonyl)phenylamino)-1 ,3, 4,6,7,9,9b- heptaazaphenalene,
• 2,5,8-tris-(4-(2-hexyldecyloxycarbonyl)phenylamino)-1 ,3, 4,6,7,9,9b- heptaazaphenalene,
• 2,5,8-tris-(4-(dodecyloxycarbonyl)phenylamino)-1 ,3,4, 6,7,9,9b-heptaazaphenalene,
• 2,5,8-tris-(4-(hexyldecyloxycarbonyl)phenylamino)-1 ,3,4, 6,7,9,9b- heptaazaphenalene,
• 2,5,8-tris-(4-(octyldecyloxycarbonyl)phenylamino)-1 ,3,4, 6,7,9,9b- heptaazaphenalene,
• 2,5,8-tris-((3-(E)-styrylphenyl)amino)-1 ,3,4,6,7,9,9b-heptaazaphenalene,
• 2,5,8-tris-(4-((3,5,5-trimethylhexyloxy)carbonyl phenyl amino)-1 ,3,4,6,7,9,9b- heptaazaphenalene,
• 2,5-bis-(3-(methoxy)phenylamino)-8-(2-( 1 -methyl- 1 H-pyrrol-2-yl)-1 , 3,4,6,7,9,9b- heptaazaphenalene,
• 2,5,8-tris-(4-((2-ethylhexyl)carbamoyl)phenylamino)-1 ,3, 4,6,7,9,9b- heptaazaphenalene,
• 2,5,8-tris-(4-(dodecyloxycarbonyl)phenylamino)-1 , 3,4,6, 7,9,9b-heptaazaphenalene,
• 2,5,8-tris-(4-(1 ,3,3-trimethylbicyclo[2.2.1]heptan-2-yloxy)phenylamino)-1 ,3,4,6,7,9,9b- heptaazaphenalene,
• 2,5,8-tris-(1 H-indol-5-ylamino)-1 , 3,4,6, 7,9,9b-heptaazaphenalene, • 2,5,8-tris-(4-((3,7-dimethyloctyloxy)carbonyl)phenylamino)-1, 3,4,6, 7,9,9b- heptaazaphenalene and 2,5,8-tris-(2-amino-4,5-dimethylphenylamino)-1 ,3,4,6,7,9,9b-heptaazaphenalene;
preferably with the aforementioned provisos;
and/or at least one of its stereoisomers, preferably enantiomers or diastereomers, a racemate or a mixture of at least two of its stereoisomers, preferably enantiomers and/or diastereomers in any mixing ratio, or at least one physiologically acceptable salt thereof, or at least one corresponding solvate thereof.
The before mentioned heptaazaphenalene derivatives of general formula (I) comprised in the inventive light-stabilizing component of the inventive composition can be obtained according to the known procedures (e.g. Shroeder, H.; Kober, E. J. Org. Chem. 1962, 27, 4262). A general scheme for obtaining heptaazaphenalene derivatives of general formula (I) is shown below (scheme 1 ).
Scheme 1
Figure imgf000042_0001
Heptaazaphenalene derivatives of general formula (I), wherein R1, R2 and R3 are the same and represent a -NR5R6 radical, wherein R5 and R6 have the meaning as defined above, can be obtained by reacting the 2,5,8-trichloro-1 ,3,4,6,7,9,9b- heptaazaphenalene derivative of formula (IV) with a derivative of general formula (V)
Figure imgf000042_0002
(IV) in a solvent comprising 1 ,4-dioxane, tetrahydrofuran, toluene, xylene (mixture of isomers), N,N-dimethylformamide, N-methylpyrrolidone or acetone, at a temperature that ranges between O0C and the boiling temperature of the solvent, preferably between room temperature and the boiling temperature of the solvent, and more preferably between 5O0C and the boiling temperature of the solvent, optionally in the presence of an organic base comprising diisopropylethylamine, triethylamine or pyridine, or an inorganic base comprising potassium carbonate, sodium hydroxide, sodium carbonate, cesium carbonate or sodium bicarbonate.
Any of the steps described in the above procedures can also be carried out in a microwave oven, employing a typical procedure of MAOS (microwave assisted organic synthesis). This standard method is well known by those skilled in the art.
Common microwave equipment may be used in preparation processes according to the present invention. The microwave irradiation may be performed at a power level of 1 to 1600 W, preferably 1 to 300 W, and particularly preferably about 70 W. The duration for the microwave irradiation may vary according to conditions such as the amount or reactant but may be in the range from 20 seconds to 60 minutes, preferably from 1 minute to 20 minutes. The reaction can be carried out at a temperature of 50-280 0C, preferably 80-200 0C, and more preferably 120-1500C, with of without solvent, under microwave irradiation. A presently preferred microwave furnace is commercially available from CEM, Inc., as model Discover®. The Discover® System incorporates temperature and pressure feedback systems, for example, an infrared temperature sensor positioned below the reaction vessel, for complete control of the reaction. As described above, according to the present invention, heptaazaphenalene derivatives can be prepared within a very short time, i.e. several seconds to several minutes, by microwave irradiation, unlike conventional techniques requiring about 12-50 hours for preparation of compounds for general formula I.
Heptaazaphenalene derivatives of general formula (I), wherein R-i, R2 and R3 are the same and represent a -NR5R6 radical, wherein R5 and R6 have the meaning as defined above and wherein one of the radicals Ri, R2 and R3 is different from the other two of these radicals Ri, R2 and R3 can be obtained by a) reacting a 2,5,8-trichloro-1 ,3,4,6,7,9)9b-heptaazaphenalene derivative of formula (IV) react with a derivative of general formula (V)
Figure imgf000044_0001
(IV) wherein R5 and R6 have the meaning as defined above, in a solvent comprising 1 ,4- dioxane, tetrahydrofuran, toluene, xylene (mixture of isomers), N1N- dimethylformamide, N-methylpyrrolidone or acetone, at a temperature that ranges between O0C and the boiling temperature of the solvent, preferably between room temperature and the boiling temperature of the solvent, and more preferably between 5O0C and the boiling temperature of the solvent; optionally in the presence of an organic base comprising diisopropyiethylamine, triethylamine or pyridine, or an inorganic base comprising potassium carbonate, sodium hydroxide, sodium carbonate, cesium carbonate or sodium bicarbonate; and b) adding to the mixture resulting from the preceding stage a second derivative of general formula (V) different from the one used in stage (a) and submitting to reflux. Any of the steps described above can be conducted trough MAOS (microwave assisted organic synthesis).
Heptaazaphenalene derivatives of general formula (I), wherein Ri, R2 and R3 are different from each other and a -NR5R6 radical, wherein R5 and R6 have the meaning as defined above, can be obtained by
a) reacting the 2, 5,8-trichloro-1 , 3,4,6,7,9, 9b-heptaazaphenalene derivative of formula (IV) with a derivative of general formula (V)
Figure imgf000045_0001
(IV)
wherein R5 and R6 have the meaning as defined above, in a solvent comprising 1 ,4- dioxane, tetrahydrofuran, toluene, tetrahydrofuran, xylene (mixture of isomers), N1N- dimethylformamide, N-methylpyrrolidone or acetone, at a temperature that ranges between O0C and the boiling temperature of the solvent, preferably between room temperature and the boiling temperature of the solvent and more preferably between 5O0C and the boiling temperature of the solvent; optionally in the presence of an organic base comprising diisopropylethylamine, triethylamine or pyridine, or an inorganic base comprising potassium carbonate, sodium hydroxide, sodium carbonate, cesium carbonate or sodium bicarbonate; b) adding to the resulting mixture a derivative of general formula (V) different from the one used in the preceding stage
NHR5R6 (V) wherein one of R5 and R6 have the meaning as defined above, and submitting to reflux; and c) adding to the mixture resulting from stage (b) a derivative of general formula (V) different from the one used in stages (a) and (b)
NHR5R6 (V) wherein R5 and R6 have the meaning as defined above.
Any of the steps described above can be conducted trough MAOS (microwave assisted organic synthesis). Heptaazaphenalene derivatives of general formula (I), wherein Ri, R2 and R3 are the same and represent a derivative of general formula (III)
Figure imgf000046_0001
can be obtained by reacting 2I5,8-trichloro-1 ,3,4,6,7,9,9b-heptaazaphenalene derivative of formula (IV) with a heterocyclic derivative or a compound of general formula (Vl)
Figure imgf000046_0002
(IV) (Vl)
wherein Ri8, R19, R20 and R21 have the meaning as defined above, in the presence of a Lewis acid comprising, FeCb, BF3, in particular aluminium trichloride, in an inert solvent comprising toluene, 1 ,1 ,2,2-tetrachloroethane, tetrahydrofuran, 1 ,2- dichlorobenzene, nitrobenzene or benzene and at a temperature that ranges between 6O0C and the boiling temperature of the solvent.
Any of the steps described above can be conducted trough MAOS (microwave assisted organic synthesis).
Heptaazaphenalene derivatives of general formula (I), wherein one of the radicals Ri, R2 and R3 represents an optionally substituted mono- or polycyclic aryl radical; an optionally substituted saturated, unsaturated or aromatic heterocyclic radical having from 5 to 10 atoms that can contain 1 , 2 or 3 heteroatoms selected from O, N and S; and the other two radicals of the radicals R-i, R2 and R3 are the same and represent a -NR5R6 radical, wherein R5 or R6 have the meaning as as defined above, can be obtained by reacting a derivative of general formula (VII) with a derivative of general formula (V):
Figure imgf000047_0001
(VII) wherein Ri represents an optionally substituted mono- or polycyclic aryl radical; an optionally substituted saturated, unsaturated or aromatic heterocyclic radical having from 5 to 10 atoms that can contain 1 , 2 or 3 heteroatoms selected from O, N and S; and
R5 and R6 have the meaning as defined above, in an inert solvent comprising 1 ,4-dioxane, tetrahydrofuran, toluene, xylene (mixture of isomers), N,N-dimethylformamide, N-methylpyrrolidone or acetone, at a temperature that ranges between O0C and the boiling temperature of the solvent, preferably between room temperature and the boiling temperature of the solvent, and more preferably between 5O0C and the boiling temperature of the solvent.
Any of the steps described above can be conducted trough MAOS (microwave assisted organic synthesis).
The derivative of general formula (VII) depicted above can be obtained by reaction of the 2,5,8-trichloro-1 , 3,4,6, 7,9,9b-heptaazaphenalene derivative of general formula (V) with an optionally substituted mono- or polycyclic aryl radical; an optionally substituted saturated, unsaturated or aromatic heterocyclic radical having from 5 to 10 atoms that can contain 1 , 2 or 3 heteroatoms selected from O, N and S, in an inert solvent comprising 1 ,4-dioxane, tetrahydrofuran, toluene, xylene (mixture of isomers), N,N-dimethylformamide, N-methylpyrrolidone or acetone, at a temperature that ranges between O0C and the boiling temperature of the solvent, preferably between room temperature and the boiling temperature of the solvent and more preferably between 5O0C and the boiling temperature of the solvent.
Any of the steps described above can be conducted trough MAOS (microwave assisted organic synthesis).
Heptaazaphenalene derivatives of general formula (I), wherein one of the radicals R-i, R2 and R3 are the same and represent an optionally substituted mono- or polycyclic aryl radical; an optionally substituted saturated, unsaturated or aromatic heterocyclic radical having from 5 to 10 atoms that can contain 1 , 2 or 3 heteroatoms selected from O, N and S; and
the third of the radicals R1, R2 and R3 represents a -NR5R6 radical, whererein R5 and R6 are defined as defined above, can be obtained by reacting the 2,5,8-trichloro- 1 ,3,4,6, 7, 9,9b-heptaazaphenalene derivative of formula (IV) with a derivative of general formula (V)
Figure imgf000048_0001
(IV)
wherein R5 and R6 have the meaning as defined above, in a solvent comprising 1 ,4- dioxane, tetrahydrofuran, toluene, xylene (mixture of isomers), N1N- dimethylformamide, N-methylpyrrolidone or acetone, at a temperature that ranges between O0C and the boiling temperature of the solvent, preferably between room temperature and the boiling temperature of the solvent, and more preferably between 5O0C and the boiling temperature of the solvent, optionally in the presence of an organic base such as diisopropylethylamine, triethylamine or pyridine, or an inorganic base comprising potassium carbonate, sodium hydroxide, sodium carbonate, cesium carbonate or sodium bicarbonate to obtain a compound of general formula (VIII),
Figure imgf000049_0001
(VIII) wherein R5 and R& have the meaning as defined above, and wherein said derivative of general formula (VIII) is reacted with a compound of general formula (Vl)
Figure imgf000049_0002
(Vl) wherein R18, R19, R20 and R21 have the meaning as defined above, in the presence of a Lewis acid comprising, FeCb, BF3, in particular aluminium chloride, in an inert solvent comprising toluene, xylene, 1 ,1 ,2,2-tetrachloroethane, tetrahydrofurane, 1 ,2- dichlorobenzene, nitrobenzene or benzene at a temperature between 6O0C and the boiling temperature of the solvent;
Any of the steps described above can be conducted trough MAOS (microwave assisted organic synthesis).
The compounds of general formula (I), wherein R20 represents a -SO3M radical, wherein M has the meaning as defined above, can be obtained by carrying out, for example, the methods disclosed in US patent 6,090,370, in particular column 5, line 59-column 6, line 8. The compounds of general formula (I), wherein an -SO3M group, with M having the meaning as defined above, has been introduced into an alkylic chain, can be obtained according to the methods described in Lewin, G. et al., J. Nat. Prod., 58 (1995) 12, 1840-1847.
The compounds of general formula (I), wherein an -N(Rn)3 + group, with Rn having the meaning as defined above, has been inserted into an alkylic chain, can be obtained for example by following the methods described in Sharma, M. L. et al., J. Indian Chem. Soc, 74(1997)4, 343-344.
A further embodiment of the present invention is a combination of light stabilizers, because it has been surprisingly found that an even more efficient light protection can be achieved, if the light-stabilizing component comprises at least one hep- taazaphenalene compound as defined above and at least one further light stabilizer (Z).
Accordingly, the light-stabilized composition comprises as light-stabilizing component at least one heptaazaphenalene compound as defined above and at least one further light stabilizer (Z) selected from the group comprising acrylate derivatives, allantoin derivatives, aminobenzoic acid derivatives, aminobenzamides derivatives, anthranilic acid derivatives, benzalmalonic acid derivatives, benzimidazole derivatives, benzoate derivatives, benzophenone derivatives, benzopyranone derivatives, benzothiazole derivatives, benzotriazole derivatives, benzoxazinone derivatives, benzoxazole derivatives, camphor derivatives, cinnamate derivatives, coumarinic acid derivatives, curcumin derivatives, cycloaliphatic ketone derivatives, dianisoylmethane derivatives, dibenzalazine derivatives, dibenzoylmethane derivatives, dioxane derivatives, ferulic acid derivatives, formamidine derivatives, formanilides, furane derivatives, glutamic acid derivatives, hindered amine derivatives, imidazoline derivatives, inorganic pigments, malonic acid derivatives, metal oxides, metal dioxides, nicotinic acid derivatives, nitrobenzamides derivatives, nitrobenzoic acid derivatives, nucleic acid derivatives, oxamide derivatives, oxanilide derivatives, p-aminobenzoic acid (PABA) derivatives, plant extracts, aromatic propanedione derivatives, propenoate derivatives, pyrimidine derivatives, quenchers, salicylate derivatives, tetrazole derivatives, triazine derivatives, tributamine derivatives, urocanic acid derivatives and vitamin Be derivatives.
The aforementioned further light stabilizers (Z) are known to those skilled in the art and are either obtainable by standard techniques or are commercially available.
According to the present invention, the term "hindered amine " mentioned above, preferably menas "sterically hindered amine", "hindered amine light stabilizer" or "HALS". Preferably, at least some of the preferably oligomeric or monomeric, hindered amine derivatives mentioned below are commercially available under their respective trade names, such as e.g. DASTIB® 845, TINUVIN® 765, TINUVIN® 791 , TINUVIN® C353, TINUVIN® XT 850, ADK STAB LA 52®, ADK STAB LA 57®, ADK STAB LA 62®, ADK STAB LA 63®, ADK STAB LA 67®, ADK STAB LA 68®, CYASORB® UV 3581 , CYASORB® UV 3604, SUMISORB® TM 61 , UVINUL® 5050 H, UVINUL® 5062 H, DIACETAM® 5, HOSTAVIN® N 20, TINUVIN® 440, TINUVIN® 494, SANDUVOR® 3050, HOSTAVIN® N 24, CHIMASSORB® 966, UVINUL® 3434 C, UVINUL 4049®, GOODRITE® UV 3034, GOODRITE® UV 3150, CHIMASSORB® 119 FL, DASTIB® 1082, FERRO® AM 806, CYASORB® UV 3346, CYASORB® UV 3529, HOSTAVIN® N 30, LICHTSCHUTZSTOFF UV 31®, FLAMESTAB® NOR 116, LUCHEM® HA-B 18 or UVASORB® HA 88.
The term "derivative", as defined in the present invention, refers to a compound in form of its respective free base, acid, salt, ester, ether, stereoisomer, such as diastereomer or enantiomer and/or solvate.
In a further preferred embodiment of the present invention, the light-stabilized composition comprises as light-stabilizing component at least one heptaazaphenalene compound as defined above and as further light stabilizer (Z) at least one compound of general formula (X)
Figure imgf000052_0001
(X)
wherein
R1x represents a hydrogen atom; an optionally substituted cycloalkyl radical from 3 to 7 carbon atoms; an aryl radical which is unsubstituted or at least mono-substituted with a group selected from aryl, halogen, an -O-C-ι-6 radical and a Ci-6 alkyl radical; a -phenyl-Ci-6 alkyl radical; a linear or branched d-β alkyl radical which is unsubstituted or at least mono-substituted with a moiety selected from -SO3MX, -N(R4x)3 + and a radical of general formula (XX)
Figure imgf000052_0002
(XX) wherein
y = O or 1 ; z = 0, 1 , 2, 3 or 4;
R R 6x R 7x R and R jncjepenc|ent of each other, each represents an unsubstituted or at least mono-substituted C1-6 alkyl radical; an -0-Ci-6 radical; an unsubstituted or at least mono-substituted aryl radical and an -OSi(R10x)3 radical; R1Ox represents a Ci-6 alkyl radical; an -O-Ci-6 radical; or an unsubstituted or at least mono-substituted aryl radical;
M represents a hydrogen atom, Na + o _ _r I KX+. ;
R represents an unsubstituted or at least mono-substituted Ci-6 alkyl radical;
R2x and R3x, independent of each other, each represents a hydrogen atom; an unsubstituted or at least monosubstituted Ci-4 alkyl radical; or an unsubstituted or at least mono-substituted aryl radical;
A1x represents a radical of general formula (X1 ) or (X2)
Figure imgf000053_0001
A represents a radical of general formula (X1 ), (X3) or (X4)
Figure imgf000053_0002
wherein
R represents a hydrogen atom; a linear or branched, saturated or unsaturated, unsubstituted or at least monosubstituted Ci-6 aliphatic radical; or a hydroxy (-OH) residue; R12x represents a hydrogen atom; a -C(=O)-OR15x radical; a -C(=O)-NR16xR17x radical; an unsubstituted or at least monosubstituted -0-C1-Ie radical; an unsubstituted or at least monosubstituted -O-phenyl radical; a Cs-7 cycloalkyl radical; a phenyl or a naphtyl radical; a phenyl or a naphtyl radical which are substituted by 1 or 2 substituents which are independently from one another selected from the group consisting of phenyl, Cl1 -O-C-ι-6 alkyl and Ci-6 alkyl; a linear or branched, saturated or unsaturated Ci_i8 aliphatic radical which is unsubstituted or at least mono-substituted with -OH, -phenyl or un moiety of general formula (XX) as defined above;
R15x, R16xand R17x, independent of each other, each represents a hydrogen atom; a linear or branched, unsubstituted or at least mono-substituted CMS alkyl radical;
R14x represents hydrogen atom; or -SO3IvT, with Mx being H, Na+ or K+;
R13x and Rl13x, independent of each other, each represents a hydrogen atom; an unsubstituted or at least monosubstituted C(=O)-Ci-i8 radical; a linear or branched CM8 alkyl radical, which is unsubstituted or at least mono-substituted with at least one hydroxy (-OH) residue, a SO3IVf moiety, a -N(R4x)3 + moiety, wherein Mx and R4x have the meaning as defined above, or a radical of general formula (XX) as defined above;
and/or
at least one compound of general formula (Is)
Figure imgf000054_0001
(IS) wherein ns= 0, 1 , 2, 3 or 4;
R1s represents a hydrogen atom; a linear or branched, unsubstituted or at least monosubstituted Ci-3 alkyl radical; or a R2s R3s"substituted phenyl- radical;
R j2s , D R2S' , D R3JSS and R Ϊ3S' , • independent of each other, each represents a hydrogen atom; a halogen atom; a hydroxy (-OH) residue; an unsubstituted or at least monosubstituted Ci-3 alkyl radical; an unsubstituted or at least monosubstituted -O- Ci-3 radical; or an unsubstituted or at least monosubstituted aryl radical;
preferably with the condition that if n=0, R2s or R3s does not represent an acryl radical;
or
R2s and R3s form together with the phenyl ring to which they are attached, an unsubstituted or at least mono-substituted naphthalene ring;
R4s and R5s, independent of each other, each represents a hydrogen atom; an unsubstituted or at least monosubstituted C1-4 alkyl radical; or an unsubstituted or at least mono-substituted aryl radical;
A1s represents a radical of general formula (Ms), (Ills) or (IVs)
Figure imgf000055_0001
A k 2s represents a radical of general formula (Ms) or (Vs)
Figure imgf000056_0001
wherein
R6s represents a hydrogen atom; a linear or branched, unsubstituted or at least monosubstituted C-ι-6 alkyl radical; or a hydroxy (-OH) residue;
R7s represents a hydrogen atom; an unsubstituted or at least monosubstituted, saturated or unsaturated, C-3-6 cycloalkyl radical; an unsubstituted or at least monosubstituted, saturated or unsaturated Cs-io cycloalkyl radical, which contains 1 , 2 or 3 heteroatom(s) as ring member(s) independently selected from the group consisting of O, N and S; an unsubstituted or at least monosubstituted aryl radical; an unsubstituted or at least monosubstituted Cs-io heteroaryl radical which contains 1 , 2 or 3 heteroatom(s) as ring member(s) independently selected from the group consisting of O, N and S; a -C(=O)-OR11s radical; a -C(=O)-NR12sR13s radical; an unsubstituted or at least monosubstituted -O-CMS radical; an unsubstituted or at least monosubstituted -O-phenyl or -O-naphtyl radical; an unsubstituted or at least monosubstituted -COR14s radical; a linear or branched, saturated or unsaturated, Ci- 18 aliphatic radical, which is unsubstituted or at least mono-substituted with at least one hydroxy (-OH) residue, a SO3MS moiety, a -N(R15s)3 + moiety or a radical of general formula (VIs)
Figure imgf000056_0002
(VIs) wherein ms = 0 or 1 ; ps = 0, 1 , 2, 3 or 4;
R i6s R i7s R i8s R i9s and R 2oSj jn(jepenc|ent of each other, each represents an unsubstituted or at least mono-substituted d-β alkyl radical; an unsubstituted or at least mono-substituted -O-C-ι-6 radical; an unsubstituted or at least mono-substituted aryl radical; or an -O-Si(R21s)3 radical;
R21s represents an unsubstituted or at least mono-substituted Ci-6 alkyl radical; an - O-C-1-6 radical; an unsubstituted or at least mono-substituted aryl radical;
R i is R i2s ancj R i3s jnc|epenc|ent of each other, each represents a hydrogen atom; a linear or branched, unsubstituted or at least monosubstituted C-MS alkyl radical; an unsubstituted or at least mono-substituted C3-6 cycloalkyl radical;
or
R12s and R13s form together with the bridging nitrogen atom an unsubstituted or at least mono-substituted, saturated 5 to 7-membered cycloaliphatic radical, which contains 1 , 2 or 3 heteroatom(s) as ring member(s) independently selected from the group consisting of O, N and S;
R14s represents an unsubstituted or at least mono-substituted Ci-i8 alkyl radical; or an unsubstituted or at least mono-substituted aryl radical;
R15s represents an unsubstituted or at least mono-substituted CMS alkyl radical;
Ms represents H, Na+ or K+;
R6s and R7s form together with the phenyl ring an unsubstituted or at least monosubstituted 9 to 15-membered polycyclic ring system;
or R6s and R14s form together with the phenyl ring an unsubstituted or at least mono- substituted 9 to 15-membered polycyclic ring system;
R8s and R9s, independent of each other, each represents a hydrogen atom; an unsubstituted or at least monosubstituted
Figure imgf000058_0001
radical; a linear or branched, saturated or unsaturated CMS aliphatic radical, which is unsubstituted or at least mono-substituted with at least one hydroxy (-OH) residue, a -SO3MS moiety, a -N(R15s)3 + moiety or a radical of general formula (VIs) as defined above;
R1Os represents a hydrogen atom; or a -SO3MS moiety with Ms representing H, Na+ or K+;
and/or
at least one compound of general formula (L1)
Figure imgf000058_0002
wherein W9 represents an alkyl or an arylcyanoacrylalkyl radical; W10 represents H, a phenyl or an alkylindoline radical; and W11 represents H or a phenyl radical;
and/or
at least one compound of formula (L2)
Figure imgf000059_0001
(L2)
and/or
at least one compound of general formula (L3)
Figure imgf000059_0002
(L3) wherein Rm represents a linear or branched, unsubstituted or at least mono- substituted CMS alkyl radical, a phenyl radical, an unsubstituted or at least mono- substituted hydroxyphenyl radical or a hydroxyalkylether; Rπ represents H, -OH, a linear or branched, unsubstituted or at least mono-substituted CMS alkyl radical, a hydroxy(alkylether)amino radical; R° represents H, -OH or a linear or branched, unsubstituted or at least mono-substituted Ci-i8 alkyl radical; and Rp represents H or a linear or branched, unsubstituted or at least mono-substituted C-M8 alkyl radical;
and/or
at least one compound of general formula (L4)
Figure imgf000060_0001
(L4) wherein Rh represents -OH, an unsubstituted or at least mono-substituted alkoxy radical, an alkenoic acid alkoxyester radical, an aryloxy radical, a hydroxyalkoxy radical, a hydroxy(alkylether)alkoxy radical, a (polymerized acrylo)alkoxyester radical or an o-alkyl acid ester radical; R' represents H, SO3H or SO3Na; Rj represents H or - OH; Rk represents H, -OH or an an unsubstituted or at least mono-substituted alkoxy radical; and R1 represents H or SO3Na;
and/or
at least one compound of general formula (L5)
Figure imgf000060_0002
wherein D Rb represent -OH;
and/or
at least one compound of general formula (L6)
Figure imgf000061_0001
(L6) wherein Rd represents -OH; Re represents a linear or branched, unsubstituted or at least mono-substituted Ci.-iβ alkyl radical, an hydroxyalkyl radical, an unsubstituted or at least mono-substituted acryloxyalkyl radical, an unsubstituted or at least mono- substituted (hydroxyphenyl)alkyl radical, an unsubstituted or at least mono- substituted (alkylester)alkyl radical, an unsubstituted or at least mono-substituted (hydroxyalkylether)oxoalkyl radical or an unsubstituted or at least mono-substituted phenylalkyl radical; R9 represents H or a linear or branched, unsubstituted or at least mono-substituted C-I--I8 alkyl radical; and Rf represents Cl, Br or I;
and/or
at least one compound of formula (L7)
Figure imgf000061_0002
and/or
at least one compound of general formula (L8)
Figure imgf000062_0001
(L8) wherein Rs represents a linear or branched, unsubstituted or at least mono- substituted C1-18 alkyl radical; Rv represents an alkylester or a cyano moiety; R1 represents a hydrogen atom or a phenyl radical and Ru represents a hydrogen atom or an -O-Ci_i8 radical;
and/or
at least one compound of general formula (L9)
Figure imgf000062_0002
wherein W3, W4, W5 and W6, independent from each other, each represents a linear or branched, unsubstituted or at least mono-substituted CMS alkyl radical
and/or
at least one compound of general formula (L10)
Figure imgf000063_0001
wherein Rr and Rq represent a linear or branched, unsubstituted or at least mono- substituted Ci_i8 alkyl radical;
and/or
Figure imgf000063_0002
(L11) wherein W7 represents a hydrogen atom, a formanilide moiety, an unsubstituted or at least mono-substituted alkylalkoxy radical and/or contains a benzimidazole radical and W8 represents a linear or branched, unsubstituted or at least mono-substituted C-1-18 alkyl radical;
and/or
at least one compound of general formula (L12)
Figure imgf000064_0001
(L12) wherein W1 represents an unsubstituted or at least mono-substituted -O-C-Mβ alkyl radical and W1 represents a linear or branched, unsubstituted or at least mono- substituted C1-18 alkyl radical;
and/or
at least one compound of general formula (L13)
Figure imgf000064_0002
(L13) wherein Rc represents a linear or branched, unsubstituted or at least mono- substituted Ci-18 alkyl radical or an unsubstituted or at least mono-substituted, saturated or unsubstituted cycloalkyl radical;
and/or
at least one compound of general formula (L14)
Figure imgf000065_0001
(L14) wherein W12 represents a hydrogen atom or -OH; W13 represents a hydrogen atom, an unsubstituted or at least mono-substituted -0-Ci-Is alkyl radical or an unsubstituted or at least mono-substituted hydroxyalkoxy radical; W14 represents a hydrogen atom or a linear or branched, unsubstituted or at least mono-substituted C|. is alkyl radical; W15 represents a hydrogen atom, a linear or branched, unsubstituted or at least mono-substituted Ci-I8 alkyl radical or an unsubstituted or an at least mono-substituted alkylester radical; W16 represents a hydrogen atom or a linear or branched, unsubstituted or at least mono-substituted Ci-i8 alkyl radical and W17 represents a linear or branched, unsubstituted or at least mono-substituted CMS alkyl radical or an at least mono-substituted alkylester radical;
and/or at least one of the stereoisomers, preferably enantiomers or diastereomers, a racemate or a mixture of at least two of the stereoisomers, preferably enantiomers and/or diastereomers in any mixing ratio, or at least one physiologically acceptable salt and/or at least one corresponding solvate of the aforementioned compounds of general formulae (X), (Is), (L1 ), (L3), (L4), (L5), (L6), (L8), (L9), (L10), (L11 ), (L12), (L13) and (L14).
The compounds of general formulae (X) and (Is) mentioned above can be prepared according to WO 2006/064366 and WO 2006/128920, respectively, which relevant disclosure is herewith introduced by reference and shall form part of the description. The compounds of formulae (L1), (L2), (L3), (L4), (L5), (L6), (L7), (L8), (L9), (L10), (L11 ), (L12), (L13) and (L14) mentioned above are known to those skilled in the art and can be obtained by standard techniques.
In a further preferred embodiment of the present invention, the light-stabilized composition comprises as light-stabilizing component at least one heptaazaphenalene compound as defined above and as further light stabilizer (Z) at least one compound selected from the group comprising isooctyl α-cyano-β, β-di- phenylacrylate, methyl α-carbomethoxycinnamate, methyl α-cyano-β-methyl-p- methoxycinnamate, butyl α-cyano-β-methyl-p-methoxy-cinnamate, methyl α- carbomethoxy-p-methoxycinnamate, N-(β-carbomethoxy-β-cyanovinyl)-2- methylindoline, ethyl-2-cyano-3,3-diphenylacrylate (UVINUL® 3035); 2-ethylhexyl-2- cyano-3,3-diphenylacrylate (UVINUL® 3039); 1.S-bis-^'-cyano-S.S1- diphenylacryloyl)oxy]-2,2-bis-{[(2-cyano-3',3I-di- phenylacryloyl)oxy]methyl}propane (UVINUL® 3035); 2-cyano-3-(2-methylindolin- yl) methylacrylate (UV Absorber Bayer 340); 2-phenyl-1 H-benzimidazole-5-sulfonic acid (GIVSORB® UV-16); dibenzoyl resorcinol, bis(4-tert-butylbenzoyl) resorcinol, benzoyl resorcinol, 2,4-di- tertbutylphenyl 3,5-di-tert-butyl-4-hydroxybenzoate, hexadecyl 3,5-di-tert-butyl-4- hydroxybenzoate, octadecyl 3,5-di-tert-butyl-4-hydroxybenzoate, 2-methyl-4,6-di-tert- butylphenyl 3,5-di-tert-butyl-4-hydroxybenzoate, hexadecyl 3,5-di-t-butyl-4- hydroxybenzoate (CYASORB® UV 2908); 3-hydroxyphenylbenzoate (SEESORB® 300); ethyl-4-[[(ethylphenylamino)methylene]amino]benzoate (GIVSORB® UV-1 ); phenyl 2-hydroxybenzoate or phenylsalicylate (SEESORB® 201 ); 2,4-di-t- butylphenyl-3,5-di-t-butyl-4-hydroxybenzoate (TINUVIN® 120); 4- bis(polyethoxy)amino acid polyethoxy ethyl ester (UVINUL® P 25); 4-t-butylphenyl 2- hydroxybenzoate, 2-hydroxy-4-octyloxybenzophenone (UVINUL® 3008); 2-hydroxy- 4-methoxybenzophenone (UVINUL® 3040); 2-hydroxy-4-methoxy-5- sulfobenzophenone or sulisobenzone (UVINUL® MS 40); 2-(4-Benzoyl-3- hydroxyphenoxy)-2-propenoic acid ethyl ester (CYASORB® UV 2098); homopolymer of 4-(2-acryloyloxyethoxy)-2-hydroxybenzophenone (CYASORB® UV 2126); 2,2'- dihydroxy-4-methoxybenzophenone or dioxybenzone (CYASORB® UV 24); 2- hydroxy-4-(2-hydroxy-3-decyloxypropoxy)benzophenone, 2-hydroxy-4-(2-hydroxy-3- octyloxypropoxy)benzophenone (MARK 1535); 2,4,4'-trihydroxybenzophenone (MAXGARD 200); 2-hydroxy-4-(isooctyloxy) benzophenone (MAXGARD 800); 2- hydroxy-4-dodecyloxybenzophenone (UVINUL® 410); 2,21-dihydroxy-4,4'-dimethoxy- 5,5'-disulfobenzophenone, disodium salt (UVINUL® 3048); 2,4- dihydroxybenzophenone (UVINUL® 400); 2,2'-dihydroxy-4,41- dimethoxybenzophenone (UVINUL® D 49); 2,2',4,4'-tetrahydroxybenzophenone (UVINUL® D 50); 2,21-dihydroxy-4-(2-hydroxyethoxy)benzophenone (UVINUL® X-19); 2-hydroxy-4-benzyloxybenzophenone (SEESORB® 105); 2-hydroxy-4- hydroxybenzophenone, 2-hydroxy-4-decyloxybenzophenone, 2-hydroxy-4,2',4'- trihydroxybenzophenone, 2-hydroxy-4-(octyloxy)benzophenone (CHIMASSORB® 81 ); 2-hydroxy-2'-hydroxy-4,4'-dimethoxybenzophenone, 3,3',4',5J- pentahydroxyflavone, quercetin, 2-(2H-benzotriazol-2-yl)-6-dodecyl-4-methyl-phenol, methyl 3-(3-(2H-benzotriazole-2-yl)-5-t-butyl-4-hydroxyphenyl) propionate/PEG 300 (TINUVIN® 213); 6-tert-butyl-2-(5-chloro-2H-benzotriazole-2-yl)-4-methylphenol (UVINUL® 3026); 6-tert-butyl-2-(5-chloro-2H-benzotriazole-2-yl)-4-methylphenol (UVINUL® 3027); 2,4-di-tert-butyl-6-(5-chloro-2H-benzotriazole-2-yl)-phenol (UVINUL® 3028); 2-(2H-benzotriazole-2-yl)-4-(1 ,1 ,3,3-tetramethylbutyl)-phenol (UVINUL® 3029); 2-(2H-benzotriazole-2-yl)-4-methylphenol (UVINUL® 3033 P); 2- (2H-benzotriazole-2-yl)-4,6-bis(1-methyl-1-phenylethyl)phenol (UVINUL® 3034); 2-(2'- hydroxy-5'-(2-hydroxyethyl))benzotriazole (NORBLOC 6000); 2-(2'-hydroxy-5'- methacrylyloxyethylphenyl)-2H-benzotriazole (NORBLOC 7966); 1 ,1 ,1- tris(hydroxyphenyl) ethane benzotriazole (THPE BZT); 5-t-butyl-3-(5-chloro-2H- benzotriazol-2-yl)-4-hydroxybenzenepropanoic acid octyl ester, 3-(5-chloro-2H- benzotriazol-2-yl)-5-t-butyl-4-hydroxybenzenepropanoic acid octyl ester (TINUVIN® 109); a-[3-[3-(2H-benzotriazol-2-yl)-5-t-butyl-4-hydroxyphenyl]-1 -oxopropyl]-w- hydroxypoly(oxy-1 ,2-ethane-diyl), a-[3-[3-(2H-benzotriazol-2-yl)-5-t-butyl-4- hydroxyphenyl]-1-oxopropyl]-w-[3-[3-(2H-benzotriazol-2-yl)-5-t-butyl-4- hydroxyphenyl]-1-oxopropoxy]poly(oxy-1 ,2-ethanediyl) (TINUVIN® 1130); 2-(2- hydroxy-3,5-di-t-butylphenyl) benzotriazole (TINUVIN® 320); 2-(2-hydroxy-3-t-butyl- 5-methylphenyl)-5-chloro-2H-benzotriazole (TINUVIN® 326); 2-(3'-5'-di-t-butyl-2I- hydroxyphenyl-)-5-chlorobenzotriazole (TINUVIN® 327); 2-(2-hydroxy-3,5-di-t- amylphenyl)benzotriazole (TINUVIN® 328); 2-(2H-benzotriazol-2-yl)-4-(1 ,1 ,3,3- tetramethylbutyl)phenol (TINUVIN® 329); 3-(2H-Benzotriazol-2-yl)-5-t-butyl-4- hydroxybenzenepropanoic acid (TINUVIN® 384); 2-(2H-benzotriazol-2-yl)-4-methyl-6- dodecylphenol (TINUVIN® 571 ); 3-(2H-benzotriazol-2-yl)-5-t-butyl-4-hydroxy-1 ,6- hexanediyl ester of benzenepropanoic acid, 3-(2H-benzotriazol-2-yl)-5-t-but-yl-4- hydroxy-methyl ester of benzenepropanoic acid (TINUVIN® 840); 2-[2-hydroxy-3,5- bis-(1 ,1-dimethylbenzyl) phenyl]-2H-benzotriazole (TINUVIN® 900); 2-(2H- benzotriazol-2-yl)-6-(1-methyl-1-phenylethyl)-4-(1 ,1 ,3- ,3-tetramethylbutyl) phenol (TINUVIN® 928); 3-(2H-benzotriazol-2-yl)-5-t-butyl-4-hydroxybenzenepropanoic acid, C7-9 branched and linear alkyl esters (TINUVIN® 99); 2-(2H-benzotriazol-2-yl)-p- cresol (TINUVIN® P); 2-(2'-hydroxy-3'-sec-butyl-5'-t-butylphenyl) benzotriazole (TINUVIN® 350); 2-(2'-hydroxy-5'-t-butylphenyl) benzotriazole (TINUVIN® PS); 2,2'- methylenebis(6-(2H-benzotriazol-2-yl)-4-1 ,1 ,3,3-tetramethylbutyl)phenol (TINUVIN® 360); 2-(2H-benzo[d][1 ,2,3]triazol-2-yl)-4,6-bis(2-phenylpropan-2-yl)phenol (TINUVIN® 234); TINUVIN® B 75; 2,21-(p-phenylene) di-3,1-benzoxazin-4-one (CYASORB® 3638); dimethyl(p-methoxybenzylidene)malonate (SANDUVOR PR 25); 3-(4-methoxyphenyl)-2-propenoic acid 2-ethylhexyl ester, octyl p-methoxycinnamate, 3-(4-methylbenzylidene)-D,L-camphor (GIVSORB® UV-15); ethyl-4- [[(methylphenylamino)methylene]amino]benzoate (GIVSORB® UV-2, TINUVIN® 101 ); N-(2-ethoxyphenyl)-N'-(4-isododecylphenyl) oxamide (SANDUVOR 3206); N-[5-t- butyl-2-ethoxyphenyl)-N'-(2-ethylphenyl) oxamide (TINUVIN® 315); N-(2- ethoxyphenyl)-N'-(2-ethylphenyl) oxamide (TINUVIN® 312); 2H-benzimidazole-2- carboxylic acid (4-ethoxyphenyl) amide (UVINUL® FK 4105); 4,4'-dioctyloxyoxanilide, 2,2'-diethoxyoxanilide, 2,2'-dioctyloxy-5,5'-di-tert-butoxanilide, 2,2'-didodecyloxy-5,5'- di-tert-butoxanilide, 2-ethoxy-2'-ethyloxanilide, N,N'-bis(3- dimethylaminopropyl)oxamide, 2-ethoxy-5-tert-butyl-2'-ethoxanilide, bis(2, 2,6,6- tetramethyl-4-piperidyl)sebacate (TINUVIN® 770); N,N'-bis(2,2,6,6-tetramethyl-4- piperidyl)- N,N'-hexamethylenebis(formamide) (UVINUL® 4050H); polymer of 2,2,4,4- tetxamethyl-7-oxa-3,20-diaza-20-(2,3-epoxi-propyl)-dispiro-(5.1.11.2)-heneicosane- 21 -one (HOSTAVIN® N 30); bis(2,2,6,6-tetramethyl-1-(octyloxy)-4-piperidinyl) decanedioic acid ester (TINUVIN® 123); ester of [(4-methoxyphenyl)methylene]-, bis(1 ,2,2,6)6-pentamethyl-4-piperidinyl)propanedioic acid (SANDUVOR® PR-31 ); copolymer of dimethlylester of 4-hydroxy-2,2,6,6-tetramethyl-1-piperaidine ethanol butanedioic acid (TINUVIN® 622) and bis(2,2,6,6-tetramethyl-4-piperidyl)sebacate (TINUVIN® 783); I .IMΗI .S.δ-triazine^^.β- triyltris^cyclohexylimino^.i-eth- anediyl) ^8(3,3,4,5,5- pentamethylpiperazinone (GOODRITE® UV 3159); 1 ,6- Hexanediamine, N, N'-bis(2,2,6,6-tetramethyl-4-piperidinyl)-polymer with 2,4,6- trichloro-1 ,3,5-triazine, reaction products with N-butyl-1-butanamine an N-butyl- 2,2,6,6-tetramethyl-4-piperidinamine (CHIMASSORB® 2020); polymethylpropyl-3- oxy-4(2,2,6,6-tetramethyl)p- iperidinyl)siloxane (UVASIL® 299); bis(2,2,6,6- tetramethyl-4-piperidyl)succinate, bis(1 ,2l2,6l6-pentamethyl-4-piperidyl)sebacate, bis(1-octyloxy-2,2)6,6-tetramethyl-4-piperidyl)sebacate, poly[[6-[(1 ,1 ,3,3,- tetramethylbutyl)amino]-1 ,3l5-triazine-2>4-diyl][(2,2,6,6-tetramethyl-4- piperidinyl)imino]-1 ,6-hexanediyl[(2I2)6,,6-tetramethyl-4-piperidinyl)imino]]) (CHIMASSORB® 944); bis(1 ,2,2,6,6-pentamethyl-4-piperidyl) n-butyl-3,5-di-tert- butyl-4-hydroxybenzylmalonate; the condensate of 1-(2-hydroxyethyl)-2,2,6,6- tetramethyl-4-hydroxypiperidine and succinic acid; the condensate of N,N'- bis(2,2,6,6-tetramethyl-4-piperidyl)hexamethylenediamine and 4-tert-octylamino-2,6- dichloro-1 ,3,5-triazine, tris(2,2,6,6-tetramethyl-4-piperidyl)nitrilotriacetate; tetrakis(2,2,6,6-tetramethyl-4-piperidyl)-1 ,2,3,4-butane-tetracarboxylate, 1 ,1'-(1 ,2- ethanediyl)bis(3,3,5,5-tetramethylpiperazinone), 4-benzoyl-2,2,6,6- tetramethylpiperidine, 4-stearyloxy-2,2,6,6-tetramethylpiperidine, bis(1 ,2,2,6,6- pentamethylpiperidyl)-2-n-butyl-2-(2-hydroxy-3,5-di-tert-butylbenzyl)malonate, 3-n- octyl-7,7,9,9-tetramethyl-1 ,3,8-triazaspiro[4.5]decan-2,4-dion, bis(1 -octyloxy-2,2,6,6- tetramethylpiperidyl)sebacate, bis(1-octyloxy-2,2,6,6-tetramethylpiperidyl)succinate, the condensate of N,N'-bis-(2,2,6,6-tetramethyl-4-piperidyl)hexamethylenediamine and 4-morpholino-2,6-dichloro-1 ,3,5-triazine; the condensate of 2-chloro-4,6-bis(4-n- butylamino-2,2,6,6-tetramethylpiperidyl)-1 ,3,5-triazine and 1 ,2-bis(3- aminopropylamino)ethane; the condensate of 2-chloro-4,6-di-(4-n-butylamino- 1 ,2,2,6,6-pentamethylpiperidyl)-1 ,3,5-triazine and 1 ,2-bis-(3- aminopropylamino)ethane; δ-acetyl-S-dodecyl-Z.Z.Θ.Θ-tetramethyl-I .S.δ- triazaspiro[4.5]decane-2,4-dione, 3-dodecyl-1-(2,2,6,6-tetramethyl-4- piperidyl)pyrrolidin-2,5-dione, 3-dodecyl-1 -(1 , 2,2,6, 6-pentamethyl-4- piperidyl)pyrrolidine-2,5-dione, a mixture of 4-hexadecyloxy- and 4-stearyloxy- 2,2,6,6-tetramethylpiperidine; a condensation product of N,NI-bis(2,2,6,6-tetramethyl- 4-piperidyl)hexamethylenediamine and 4-cyclohexylamino-2,6-dichloro-1 ,3,5-triazine; N-(2,2,6,6-tetramethyl-4-piperidyl)-n-dodecylsuccinimid, N-(1 ,2,2,6,6-pentamethyl-4- piperidyl)-n-dodecylsuccinimid, 2-undecyl-7,7,9,9-tetramethyl-1-oxa-3,8-diaza-4-oxo- spiro[4,5]decane, a reaction product of ZJ.Θ.Θ-tetramethyl^-cycloundecyl-i-oxa-S, 8- diaza-4-oxospiro [4,5]decane and epichlorohydrine, titanium dioxide, zinc oxide, zinc cerium oxide, carbon black, cadmium sulfide, cadmium selenide, chromium oxide, iron oxide, lead oxide, zirconium oxide, bis (1 ,2,2,6,6-pentamethyl-4-piperidinyl)-2- butyl-2-(4-hydroxy-3,5-di-tert.-butylbenzyl)propanedioate (TINUVIN® 144); 4-t-butyl- 4'-methoxydibenzoylmethane, avobenzone (GIVSORB® UV-14); nickel dibutyldithiocarbamate; thio bis2,2'-[4-(1 ,1 >3,3-tetramethylbutyl)-phenyl- ]nickel-2- ethyl hexanoate; n-butylamine-nickel-2,2'-thio bis(4-t-octylphenolate), nickel-bis-[2,2'- thio bis(4-t-octylphenolate)], octylphenyl salicylate, 4-t-butylphenylsalicylate (SEESORB® 202); S.S.δ-trimetylcyclohexylsalicylate or homomentyylsalicylate (NEO HELIOPAN HMS); menthyl-o-aminobenzoate (NEO HELIOPAN MA); 2-[4,6-bis(2,4- dimethylphenyl)-1 ,3,5-triazin-2-yl]-5-octyloxyphenol (CYASORB® UV 1164); confidential triazine derivative (TINUVIN® 1545); 2-(4,6-diphenyl-1 ,3,5-triazin-2-yl)-5- hexyloxyphenol (TINUVIN® 1577 FF); 2-[4-((2-hydroxy-3-dodecyloxypropyl)oxy)-2- hydroxyphenyl]-4,6-bis(2,4-dimethylphenyl)-1 ,3,5-triazine (TINUVIN® 400); 2,4,6- Trianilino-p-tcarbo^'-ethylhexyl-i'-oxyH ,3,5-triazine (UVINUL® T-150); 2, 4-bis(2, 4- dihydroxyphenyl)-6-(1-methyl-1 H-pyrazol-5-yl)-1 ,3,5-triazine, 2,4-bis{[4-(2- ethylhexyloxy)-2-hydroxy]phenyl}-6-(1-methyl-1 H-pyrazol-5-yl)-1 ,3,5-triazine, 2-[2, 4- bis (2-ethylhexyloxy)phenyl]-4-[4-(2-ethylhexyloxy)-2-hydroxyphenyl]-6-(1 -methyl-1 H- pyrazol-5-yl)-1 ,3,5- triazine, 2,4-bis(2, 4-dihydroxyphenyl)-6(1-phenyl-1 H-pyrazol-5- yl)-1 ,3,5-triazine, 2,4-bis{[4-(2-ethylhexyloxy)-2-hydroxy]phenyl}-6-(1-phenyl-1 H- pyrazol-5-yl)-1 ,3,5-triazine, 2,4-bis [4-(butoxycarbonyl)phenylamino]-6-(1 -methyl-1 H- pyrazol-5-yl)-1 ,3,5-triazine, 2,4-bis{4-[(2-(ethylhexyloxy)carbonyl]phenylamino}-6-(1 - methyl-1 H-pyrazol-5-yl)-1 ,3,5-triazine, 2,4-bis [4-(butoxycarbonyl)phenylamino]-6-(1- phenyl-1 H-pyrazol-5-yl)-1 ,3,5-triazine, 2,4-bis{4-[(2- ethylhexyloxy)carbonyl]phenylamino}-6-(1-phenyl-1 H-pyrazol-5-yl)-1 ,3,5-triazine, 2- [(4-butoxycarbonyl)phenylamino]-4,6-bis(1 -methyl-1 H-pyrazol-5-yl)-1 ,3,5-triazine, 2- (1-benzyl-1 H-pyrrol-2-yl)-4,6-bis(2,4-dihydroxyphenyl)-1 ,3,5-triazine, 2-(1-benzyl-1 H- pyrrol-2-yl)-4,6-bis[4-(2-ethylhexyloxy)-2-hydroxyphenyl]-1 ,3,5-triazine, 2-(1 -benzyl- 1 H-pyrrol-2-yl)-4,6-bis[4-(butoxycarbonyl) phenylamino]-1 ,3,5-triazine, 2-(1-benzyl- 1 H-pyrrol-2-yl)-4,6-bis(biphenyl-4-ylamino)-1 ,3,5-triazine, 2-(1-benzyl-1 H-pyrrol-2-yl)- 4,6-bis(4-benzoylphenylamino)-1 ,3,5-triazine, 2-(1-benzyl-1 H-pyrrol-2-yl)-4,6-bis(9- oxo-9H-fluoren-3-ylamino)-1 ,3,5-triazine, 2-(1-benzyl-1 H-pyrrol-2-yl)-4,6-bis[4- (imidazo[1 ,2-a]pyridin-2-yl)phenylamino]-1 ,3,5-triazine, 2-(1-benzhydryl-1 H-pyrrol-2- yl)-4,6-bis[4-(butoxycarbonyl)phenylamino]-1 ,3,5-triazine, 2-(1-benzyl-1 H-pyrrol-2-yl)- 4,6-bis[4-(6,6-dimethyl-4-oxo-4,5, 6, 7-tetrahydroindol-1-yl)phenylamino]-1 ,3,5-triazine, 2-(1 -benzyl-1 H-pyrrol-2-yl)-4,6-bis[4-((2-ethylhexyloxy)carbonyl)phenylamino]-1 ,3,5- triazine, 2-(1-benzyl-1 H-pyrrol-2-yl)-4,6-bis[4-1 H-imidazo[1 ,2-a]pyridin-2- yl)phenylamino]-1 ,3,5-triazine, 2-(1 -benzyl-1 H-pyrrol-2-yl)-4,6-bis[4-(1 H- benzo[d]imidazol-2-yl)phenylamino]-1 ,3,5-triazine, 2-(1-benzyl-1 H-pyrrol-2-yl)-4,6- bis[4-(1 H-pyrazol-1-yl)phenylamino]-1 ,3,5-triazine, 2-(1-benzyl-1 H-pyrrol-2-yl)-4,6- bis[naphthalen-2-ylamino]-1 ,3,5-triazine, 2-(1-benzyl-1 H-pyrrol-2-yl)-4,6-bis[4-((E)-3- ethoxy-3-oxoprop-1-enyl)phenylamino]-1 ,3,5-triazine and 2-(1-benzyl-1 H-pyrrol-2-yl)- 4,6-bis[4-(E)-styrylphenylamino]-1 ,3,5-triazine;
and/or at least one of the stereoisomers, preferably enantiomers or diastereomers, a racemate or a mixture of at least two of the stereoisomers, preferably enantiomers and/or diastereomers in any mixing ratio, or at least one physiologically acceptable salt and/or at least one corresponding solvate of the aforementioned compounds.
In a further preferred embodiment of the present invention, the light-stabilized composition comprises as light-stabilizing component at least one heptaazaphenalene compound as defined above and as further light stabilizer (Z) at least one compound selected from the group comprising 2-ethylhexyl 2-cyano-3,3'- diphenylacrylate, ethyl 2-cyano-3,3'-diphenylacrylate, polymer of N-{(2 and 4)[(2- oxoborn-3-ylidene)methyl]benzyl}acrylamide, methyl 4-aminobenzoate, butyl 4- aminobenzoate, 5-methyl-2-(1-methylethyl)-cyclohexyl 2-aminobenzoate, glyceryl aminobenzoate, 2-ethylhexyl-p-dimethylethyl-aminobenzoate, 4-aminobenzamide, homomethyl-N-acetyl-anthranilic acid, menthyl antrhanilate, 2-(1 H-benzimidazol-2- yl)-4-methoxyphenol, 2,2'-bis(benzimidazole), monosodium salt of 2-2'-bis-(1 ,4- phenylene)1 H-benzimidazole-4,6-disulphonic acid, 2-phenylbenzimidazole-5- sulphonic acid, 5,51,6,61-tetramethyl-2,2'-bis(benzimidazole), 5,5'-dimethyl-2,2'- bis(benzimidazole), 6-methoxy-2,2'-bis(benzimidazole), 1 ,4-phenylenebis(2- benzimidazolyl), 1 ,2-phenylenebis)benzimidazolyl), 1 ,4-phenylenebis(N-2-ethylhexyl- 2-benzimidazolyl), 1 ,4-phenylenebis(N-tri-methylsilylmethyl-2-benzimidazolyl), 2-(1 H- benzimidazol-2-yl)benzothiazole, 2-(1 H-benzimidazol-2-yl)benzoxazole, N1N'- dimethyl-2,2'-bis(benzimidazole), phenylbenzimidazole-5-sulfonic acid (Ensulizole) and its salts , 2-2'-bis-(1 ,4-phenylene)1 H-benzimidazole-4,6-disulphonic acid, 3-me- thylbutyl 4-(dimethylamino)benzoate, 3,3,5-trimethylcyclohexyl 2-hydroxybenzoate (Homosalate), ethyl 4-aminobenzoate, 4,4-((6-(((1 ,1-di- methylethyl)amino)carbonyl)phenyl)amino) 1 ,3,5-triazine-2,4-diyl)diimino)bis-,bis-(2- ethyl-hexyl)ester) benzoic acid, 2,4-dihydroxy-benzophenone (Benzophenone-1 ), 2,2'-dihydroxy-4-methoxy-benzophenone (dioxybenzone, Benzophenone-8), 2,2'- dihydroxy^^'-dimethoxy-benzophenone, 2,2',4,4'-tetrahydroxy-benzophenone, 2- hydroxy-4-methoxy-4'-methyl-benzophenone, hydroxymethoxy-benzophenone sulfonic acid, (2-Hydroxy-4-methoxyphenyl)-phenylmethanone (Benzophenone-3), 2- hydroxy-4-methoxy-benzophenone-5-sulfonic acid (Benzophenone-4) and its salts, 4- phenyl-benzophenone, 2-ethylhexyl-4'-phenyl-benzophenone-2-carboxylate, 2- hydroxy-4-n-octoxy-benzophenone, 4-hydroxy-3-carboxy-benzophenone, 4-(2-β- glucopyranosiloxy)-propoxy-2-hydroxybenzophenone, dihydroxy-dimethoxy-di- sulfobenzophenone, 2-benzothiazol-2-ylphenol, [2,4'-dihydroxy-3-(2H-benzotriazol-2- yl)-5-(1 ,1.S.S-tetramethylbutyl^'-n-octoxy-δ'-benzoylJ-diphenylmethane, 2,2'- hydroxy-5-methylphenyl-benzotriazole, 2-(2'-hydroxy-5l-t-octylphenyl)benzotriazole, 2-(2'-hydroxy-5'-methylphenyl)benzotriazole, 2,2'-methylene-bis-6-(2H-benzotriazol- 2-yl)-4-(tetramethyl-butyl)-1 ,1 ,3,3-phenol, 2-benzoxazole-2-yl-4-methylphenol, 2- phenyl-5-methylbenzoxazole, 1 ,4-phenylenebis(2-benzoxazolyl), 1 ,3-phenylenebis(2- benzoxazolyl), 1 ,2-phenylenebis(2-benzoxazolyl), 2-(2-benzofuryl)-benzoxazole, 2- (benzofuryl)-5-methylbenzoxazole, 2-(3-methyl-2-benzofuryl)benzoxazole, 3-(4'- methylbenzylidene)-D,L-camphor, terephthalylidene dicamphor sulphonic acid, 3- benzylidene-D,L-camphor, 4-benzylidene-D,L-camphor, di-tert-butyl hydroxybenzylidene camphor, benzylidene camphor sulphonic acid, camphor benzalkonium methosulfate, polyacrylamido-methyl benzylidene camphor, ethylhexyl methoxycinnamate, diethanolamine p-methoxy cinnamate, isopropyl-p-acetamido cinnamate, octyl cinnamate, ethyl-4-isopropylcinnamate, methyl-2,5-diisopropyl cinnamate, ethyl-2,4-diisopropylcinnamate, methyl-2,4-diisopropylcinnamate, propyl- p-methoxycinnamate, isopropyl-p-methoxycinnamate, diisopropylcinnamate esters, isoamyl-p-methoxycinnamate, cyclohexyl-p-methoxycinnamate, ethyl-α-cyano-β- phenylcinnamate, 2-ethylhexyl-α-cyano-β-phenylcinnamate, glycerin-mono-2-ethyl- hexanoyl-diparamethoxycinnamate, glyceryl octanoate-di-p-methoxycinnamate, DEA- methoxycinnamate, methyl-bis(trimethyl-siloxy)silyl-isopentyl-trimethoxycinnamate, ethyl-α-cyano-3,5-dimethoxy-4-hydroxy cinnamate, ethyl-α-acetyl-3,5-dimethoxy-4- hydroxy cinnamate, iso-propyl-α-acetyl-3,5-dimethoxy-4-hydroxy cinnamate, iso- amyl-α-acetyl-3,5-dimethoxy-4-hydroxy cinnamate, 2-ethylhexyl-α-acetyl-3,5- dimethoxy-4-hydroxy cinnamate, ethyl-a-cyano-3-methoxy-4-hydroxy cinnamate, ethyl-α-acetyl-3-methoxy-4-hydroxy cinnamate, iso-propyl-α-acetyl-3-methoxy-4- hydroxy cinnamate, iso-amyl-a-acetyl-3-methoxy-4-hydroxy cinnamate, 2-ethylhexyl- α-acetyl-3-methoxy-4-hydroxy cinnamate, 7-ethylamino-4-methylcoumarin, 7,8- dihydroxycoumarin, 6,7-dihydroxycoumarin, 7-hydroxycoumarin, 4-methyl-7- hydroxycoumarin, diacetycurcumin, tetrahydrocurcumin diacetate, dianisoylmethane, dibenzalazine, butyl methoxydibenzoylmethane (Avobenzone), 2- methyldibenzoylmethane, 4-methyldibenzoylmethane, 4-isopropyldibenzoylmethane, 4-tert-butyldibenzoylmethane, 2,4-dimethyldibenzoylmethane, 2,5- dimethyldibenzoylmethane, 4,4'-diisopropyldibenzoylmethane, 4,4'- dimethoxydibenzoylmethane, 2-methyl-5-isopropyl-41-methoxydibenzoylmethane, 2- methyl-5-tert-butyl-4'-methoxydibenzoylmethane, 2,4-dimethyl-4'- methoxydibenzoylmethane, 2,6-dimethyl-4-tert-butyl-4I-methoxydibenzoylmethane, ferulic acid, dimethicodiethylbenzalmalonate, diethyl-3,5-dimethoxy-4-hydroxy benzylidene malonate, di-(2-ethylhexyl)-3,5-dimethoxy-4-hydroxy benzylidene malonate, diisoamyl-3,5-dimethoxy-4-hydroxy benzylidene malonate, didodecyl-3,5- dimethoxy-4 hydroxy benzylidene malonate, dipalmitoyl-3,5-dimethoxy-4-hydroxy benzylidene malonate, di-isopropyl-3,5-dimethoxy-4-hydroxy benzylidene malonate, diethyl-3-methoxy-4-hydroxy benzylidene malonate, di-(2-ethylhexyl)-3-methoxy-4- hydroxy benzylidene malonate, diisoamyl-3-methoxy-4-hydroxy benzylidene malonate, didodecyl-3-methoxy-4-hydroxy benzylidene malonate, dipalmitoyl-3- methoxy-4-hydroxy benzylidene malonate, di-isopropyl-3-methoxy-4-hydroxy benzylidene malonate, hydrolyzed aspergillus sp. extract ferment, 4-nitrobenzamide, 4-nitrobenzoic acid, p-aminobenzoic acid (PABA), PABA-monoglycerinester, N, N- dipropoxy-PABA-ethylester, N,N-diethoxy PABA-ethylester, N,N-dimethyl PABA- ethylester, N,N-dimethyl PABA-butylester, PEG-25 PABA, N,N-dimethyl PABA- amylester, N,N-dimethyl PABA-octlylester (2-ethylhexyl 4-(dimethylamino)benzoate, Padimate O), octyl dimethyl PABA, ethyl-dihydroxypropyl-PABA, isoamyl dimethyl PABA (3-methylbutyl 4-(dimethylamino)benzoate, Padimate A), 1-(3,4- dimethoxyphenyl)-4,4-diemthyl-1 ,3-pentanedione, 5-(3,3-Dimethyl-2-norbornyliden)- 3-pentane-2-one, 1 -(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1 ,3-dione, dipropylene glycol salicylate, 2-ethylhexyl 2-cyano-3,3-diphenyl-2-propenoate (Octocrylene), hydrolyzed soy extract, hydrolyzed linseed extract, sunflower seed extract, grape seed extract, pinus pinaster bark extract, pinus pinaster bud extract, ginseng extract ferment, spirulina platensis powder, p-tert-butylphenyl salicylate, p- octylphenyl salicylate, 2-ethylhexyl salicylate (octyl salicylate), amyl salicylate, menthyl salicylate, homomenthyl salicylate, benzyl salicylate, p-isopropanol-phenyl salicylate, TEA-salicylate, 2-(2H-benzotriazol-2-yl)-4-methyl-6-[2-methyl-3-[1 ,3,3,3- tetramethyl-1-[(trimethylsilyl)oxy]disiloxanyl]propyl]-phenol (Mexoryl XL), 2-[p-(tert- butylamido)anilino]-4,6-bis[p-(2'-ethylhexyl-1 '-oxycarbonyl)anilino]-1 ,3,5-triazine (INCI name: Diethylhexyl Butamido Triazone), 2,4,6-tris[4-(2-ethylhexyl-oxycarbonyl)- anilino]-1 ,3,5-triazine (INCI name: Ethylhexyl Triazone), (1 ,3,5)-triazine-2,4-bis((4-2- ethyl-hexyloxy)-2-hydroxy)-phenyl)-6-(4-methoxy-phenyl) (bemotrizinol), octyl triazone (CAS-no.: 88122-99-0), urocanic acid, ethyl-urocanic acid, talc, kaolin, calcium carbonate, bisoctrizole (CAS-no.: 103597-45-1), bornelone (CAS-no.: 2226- 11-1 ), 2-hydroxy-1 ,4-naphthochinone (Lawsone, CAS-no.: 83-72-7), petrolatum red, phenol sulphonate, sodium 3,4-dimethylphenyl-glyoxylate, 3,3'-(1.4- phenylenedimethylene-bis-(7,7-dimethyl-2-oxobicyclo-[2,2,1]hept-1-yl- methanesufonic acid, α-(2-oxoborn-3-ylidene)-toluene-4-sulphonic acid, 2-(2H- benzotriazole-2-yl)-4-methyl-6-[2-methyl-3-[1 ,3,3,3-tetramethyl-1- [(trimethylsilyl)oxy]disiloxanyl]propyl]-phenol (INCI name: drometrizole trisiloxane, DTS), digalloyl trioleate, dimethicone/PEG-15 crosspolymer, ethylhexyl-bis-isopentyl- benzoxazolyl-phenyl melamine and 2-ethylhexyl-dimethoxy-benzylidene-dioxo- imidazolidine propionate;
and/or at least one of its stereoisomers, preferably enantiomers or diastereomers, a racemate or a mixture of at least two of the stereoisomers, preferably enantiomers and/or diastereomers in any mixing ratio, or at least one physiologically acceptable salt and/or at least one corresponding solvate of the afore mentioned compounds.
In a further preferred embodiment of the present invention, the light-stabilized composition comprises as light-stabilizing component at least one heptaazaphenalene compound selected from the group comprising
• 2, 5,8-tris-(4-(butoxycarbonyl)phenylamino)-1 ,3,4,6,7,9, 9b- heptaazaphenalene,
• 2,5,8-tris-(4-(2-ethylhexyloxycarbonyl)phenylamino)-1 ,3, 4,6,7,9,9b- heptaazaphenalene,
• 2,5,8-tris-(4-(imidazo[1 ,2-a]pyridin-2-yl)-phenylamino) -1 ,3,4,6,7,9,9b- heptaazaphenalene,
• 2,5,8-tris-(4-(4,5,6,7-tetrahydro-2,6,6-trimethyl-4-oxo indol-1 -yl)phenylamine)- 1 ,3,4,6,7,9,9b-heptaazaphenalene,
• 2,5,8-tris-(biphenyl-4-ylamino)-1 ,3,4,6,7,9,9b-heptaaza phenalene,
• 2,5,8-tris-(4-(1 H-benzo[d]imidazol-2-yl)phenylamino)-1 , 3,4,6,7,9,9b- heptaazaphenalene, • 2,5-bis-(biphenyl-4-ylamino)-8-(4-(butoxycarbonyl)phe nylamino)- 1 ,3,4,6, 7, 9,9b-heptaazaphenalene,
• 2-(biphenyl-4-ylamino)-5-(4-(butoxycarbonyl)phenylami no)-8-(4-(2- ethylhexyloxycarbonyl)phenylamino)-1 ,3,4, 6,7,9,9b-heptaazaphenalene,
• 2,5,8-tris-(2,4-dihydroxyphenyl)-1 , 3,4,6, 7,9,9b-heptaaza phenalene,
• 2,5-dichloro-8-(1 -methyl-1 H-pyrrol-2-yl)-1.SAβy.θ.θb-heptaazaphenalene,
• 2, 5-bis-(4-(butoxycarbonyl)phenylamino)-8-(2-(1 -methyl-1 H-pyrrol-2-yl)- 1 , 3,4,6, 7,9,9b-heptaazaphenalene,
• 2-(4-(carboxy)phenylamino)-5,8-bis-(4-methylphenyl)-1 ,3, 4,6,7,9,9b- heptaazaphenalene,
• 2,5,8-tris-(4-(4,5,6,7-tetrahydro-2,6,6-trimethyl-4-oxo indol-1 -yl)phenylamine)- 1 ,3,4,6, 7, 9,9b-heptaazaphenalene,
• 2, 5-bis-(4-(butoxycarbonyl)phenylamino)-8-(1 -methyl-1 H-pyrrol-2-yl)- 1 ,3,4,6,7,9,9b-heptaazaphenalene,
• 2,5-bis(2,4-dihydroxyphenyl)-8-(1 -methyl-1 H-pyrazol-5-yl)-1 ,3,4,6,7,9,9b- heptaazaphenalene,
• 2,5-bis{[4-(2-ethylhexyloxy)-2-hydroxy]phenyl}-6-(1 -methyl-1 H-pyrazol-5-yl)- 1 ,3,4,6, 7, 9,9b-heptaazaphenalene,
• 2-[2,4-bis(2-ethylhexyloxy)phenyl]-5-[4-(2-ethylhexyl oxy)-2-hydroxyphenyl]-8- (1 -methyl-1 H-pyrazol-5-yl)-1 ,3, 4,6,7,9,9b-heptaazaphenalene,
• 2,5-bis(2,4-dihydroxyphenyl)-8-(1 -phenyl-1 H-pyrazol-5-yl)-1 ,3,4,6,7,9,9b- heptaazaphenalene,
• 2, 5-bis{[4-(2-ethylhexyloxy)-2-hydroxy]phenyl}-8-(1 -phenyl-1 H-pyrazol-5-yl)- 1 ,3,4,6, 7,9, 9b-heptaazaphenalene,
• 2, 5-bis[4-(butoxycarbonyl)phenylamino]-8-(1 -methyl-1 H-pyrazol-5-yl)- 1 ,3,4,6,7,9,9b-heptaazaphenalene,
• 2, 5-bis{4-[(2-(ethylhexyloxy)carbonyl]phenylamino}-8-(1 -methyl-1 H-pyrazol-5- yl)-1 , 3,4,6, 7,9,9b-heptaazaphenalene,
• 2,5-bis[4-(butoxycarbonyl)phenylamino]-8-(1 -phenyl-1 H-pyrazol-5-yl)- 1 , 3,4,6, 7,9,9b-heptaazaphenalene,
• 2,5-bis{4-[(2-ethylhexyloxy)carbonyl]phenylamino}-8-(1 -phenyl-1 H-pyrazol-5- yl)-1 , 3,4,6, 7,9,9b-heptaazaphenalene,
• 2-(1-benzyl-1 H-pyrrol-2-yl)-5,8-bis(2,4-dihydroxy phenyl)-1 ,3,4,6,7,9,9b- heptaazaphenalene,
• 2-(1-benzyl-1 H-pyrrol-2-yl)-5,8-bis[4-(2-ethylhexyloxy)-2-hydroxyphenyl]- 1 ,3,4,6, 7, 9,9b-heptaazaphenalene,
• 2-(1-benzyl-1 H-pyrrol-2-yl)-5,8-bis[4-(butoxycarbonyl) phenylamino]- 1 ,3,4,6,7,9,9b-heptaazaphenalene,
• 2-(1 -benzyl-1 H-pyrrol-2-yl)-5,8-bis(biphenyl-4-ylamino)-1 ,3,4,6,7,9,9b- heptaazaphenalene,
• 2-(1 -benzyl-1 H-pyrrol-2-yl)-5,8-bis(4-benzoylphenylami-no)-1 ,3,4,6,7,9,9b- heptaazaphenaiene,
• 2-(1-benzyl-1 H-pyrrol-2-yl)-5,8-bis(9-oxo-9H-fluoren-3-ylamino)-1 ,3,4,6,7,9,9b- heptaazaphenaiene,
• 2-(4-(tert-butylcarbamoyl)phenylamino)-5,8-bis-(4-(2- ethylhexyloxycarbonyl)phenylamino)-1 , 3,4,6, 7,9, 9b-heptaazaphenalene,
• 2,5-bis-[(4-(2-ethylhexyloxy)-2-hydroxy)-phenyl]-8-(4-methoxyphenyl)- 1 ,3,4,6,7,9,9b-heptaazaphenalene,
• 2-(2-ethylhexylamino)-5,8-bis-(4-(5-(1 ,1-dimethylpropyl)benzo[d]oxazol-2- yl)phenylamino)-1 , 3,4,6,7,9, 9b-heptaazaphenalene, • 2,5,8-tris-(4-(1 H-pyrazol-1-yl)phenylamino)-1 ,3,4,6, 7, 9,9b- heptaazaphenalene
• 2,5,8-tris-(4-benzoylphenylamino)-1 ,3,4,6, 7,9,9b-hepta azaphenalene,
• 2, 5, 8-tris-(4-butoxy-2-hydroxyphenyl)-1 , 3,4,6,7,9, 9b-heptaazaphenalene,
• 2,5,8-tris-(naphthalen-2-ylamino)-1 ,Z,4,QJ,9,9b-hep\.a azaphenalene,
• 2,5-bis-(4-(butoxycarbonyl)phenylamino)-8-(2-(1-methyl-1 H-indol-3-yl)- 1 ,3,4,6,7,9,9b-heptaazaphenalene,
• 2,5,8-tris-(biphenyl-4-yloxy)-1 , 3,4,6,7, 9,9b-heptaaza phenalene,
• 2,5,8-tris-(3-methoxyphenylamino)-1 , 3,4,6, 7,9,9b-hepta azaphenalene,
• 2,5,8-tris-(4-methoxyphenylamino)-1 , 3,4,6, 7,9,9b-hepta azaphenalene,
• 2,5,8-tris-(4-((E)-3-ethoxy-3-oxoprop-1 -enyl)phenyl amino)-1 ,3,4,6,7,9,9b- heptaazaphenalene,
• 2,5,8-tris-(methoxycarbonyl-4'-biphenyl-4-ylamino)-1 ,3, 4,6,7,9,9b- heptaazaphenalene,
• 2,5,8-tris-(4-(methoxycarbonyl)phenylamino)-1 l3,4,6, 7,9,9b- heptaazaphenalene,
• 2,5,8-tris-(4-(1 H-benzo[d]imidazol-2-yl)-3-hydroxy phenylamino)- 1 ,3,4,6, 7,9, 9b-heptaazaphenalene,
• 2,5, 8-tris-(4-(phenylamino)phenylamino)-1 , 3,4,6, 7,9, 9b-heptaazaphenalene,
• 2,5,8-tris-((4-(E)-styrylphenyl)amino)-1 ,3,4,6,7,9,9b-heptaazaphenalene,
• 2,5,8-tris-(2-ethylhexylamino)-1 ,3,4,6, 7,9,9b-heptaaza phenalene,
• 2,5,8-tris-(4-(L-menthylcarbonyl)phenylamino)-1 ,3,4,6, 7,9,9b- heptaazaphenalene,
• 2,5,8-tris-(4-((3,3,5-trimethylcyclohexyloxy)carbonyl) phenylamino)- 1 ,3,4,6, 7,9, 9b-heptaazaphenalene,
• 2,5,8-tris-(4-((E)-3-(2-ethylhexyloxy)-3-oxoprop-1 -enyl) phenylamino)- 1 ,3,4,6,7,9,9b-heptaazaphenalene,
• 2-(3-((E)-3-(2-ethylhexyloxy)-3-oxoprop-1 -enyl)phenyl amino)-5,8-bis-(4-((E)- 3-(2-ethylhexyloxy)-3-oxoprop-1-enyl)phenylamino)-1 ,3,4,6, 7,9, 9b- heptaazaphenalene,
• 2,5,8-tris-(3-nitrophenylamino)-1 ,3,4,6,7,9,9b-heptaaza phenalene,
• 2,5,8-tris-(4-(2-butyloctyloxycarbonyl)phenylamino)-1 ,3, 4,6,7,9,9b- heptaazaphenalene,
• 2,5,8-tris-(4-(2-hexyldecyloxycarbonyl)phenylamino)-1 ,3, 4,6,7,9,9b- heptaazaphenalene,
• 2,5,8-tris-(4-(dodecyloxycarbonyl)phenylamino)-1 ,3,4, 6,7,9,9b- heptaazaphenalene,
• 2,5,8-tris-(4-(hexyldecyloxycarbonyl)phenylamino)-1 ,3,4, 6,7,9,9b- heptaazaphenalene,
• 2,5,8-tris-(4-(octyldecyloxycarbonyl)phenylamino)-1 ,3,4, 6,7,9,9b- heptaazaphenalene,
• 2,5,8-tris-((3-(E)-styrylphenyl)amino)-1 ,3,4,6,7,9,9b-heptaazaphenalene,
• 2>5,8-tris-(4-((3,5,5-trimethylhexyloxy)carbonyl phenyl amino)-1 , 3,4,6, 7,9,9b- heptaazaphenalene,
• 2,5-bis-(3-(methoxy)phenylamino)-8-(2-(1 -methyl-1 H-pyrrol-2-yl)- 1 ,3,4,6,7,9,9b-heptaazaphenalene,
• 2,5,8-tris-(4-((2-ethylhexyl)carbamoyl)phenylamino)-1 ,3, 4,6,7,9,9b- heptaazaphenalene,
• 2,5,8-tris-(4-(dodecyloxycarbonyl)phenylamino)-1 ,3,4,6,7,9,9b- heptaazaphenalene, • 2,5,8-tris-(4-(1 ,3,3-trimethylbicyclo[2.2.1]heptan-2-yloxy)phenylamino)- 1 ,3,4,6, 7, 9,9b-heptaazaphenalene,
• 2,5,8-tris-(1 H-indol-5-ylamino)-1 , 3,4,6,7, 9,9b-heptaazaphenalene,
• 2, 5,8-tris-(4-((3,7-dimethyloctyloxy)carbonyl)phenylamino)-1 ,3,4,6,7,9,9b- heptaazaphenalene and
2, 5,8-tris-(2-amino-4,5-dimethylphenylamino)-1 ,3,4,6,7,9,9b- heptaazaphenalene; and as a further light stabilizer (Z) at least one compound selected from the group comprising isooctyl α-cyano-β, β-di-phenylacrylate, methyl α- carbomethoxycinnamate, methyl α-cyano-β-methyl-p-methoxycinnamate, butyl α- cyano-β-methyl-p-methoxy-cinnamate, methyl α-carbomethoxy-p-methoxycinnamate, N-(β-carbomethoxy-β-cyanovinyl)-2-methylindoline, ethyl-2-cyano-3,3- diphenylacrylate (UVINUL® 3035); 2-ethylhexyl-2-cyano-3,3-diphenylacrylate (UVI NUL® 3039); 1 ,3-bis-[(2'-cyano-3,3'-diphenylacryloyl)oxy]-2,2-bis-{[(2-cyano-3I,31- di- phenylacryloyl)oxy]methyl}propane (UVINUL® 3035); 2-cyano-3-(2-methylindolin- yl) methylacrylate (UV Absorber Bayer 340); 2-phenyl-1 H-benzimidazole-5-sulfonic acid (GIVSORB® UV-16); dibenzoyl resorcinol, bis(4-tert-butylbenzoyl) resorcinol, benzoyl resorcinol, 2,4-di-tertbutylphenyl 3,5-di-tert-butyl-4-hydroxybenzoate, hexadecyl 3,5-di-tert-butyl-4-hydroxybenzoate, octadecyl 3,5-di-tert-butyl-4- hydroxybenzoate, 2-methyl-4,6-di-tert-butylphenyl 3,5-di-tert-butyl-4- hydroxybenzoate, hexadecyl 3,5-di-t-butyl-4-hydroxybenzoate (CYASORB® UV 2908); 3-hydroxyphenylbenzoate (SEESORB® 300); ethyl-4- [[(ethylphenylamino)methylene]amino]benzoate (GIVSORB® UV-1 ); phenyl 2- hydroxybenzoate or phenylsalicylate (SEESORB® 201 ); 2,4-di-t-butylphenyl-3,5-di-t- butyl-4-hydroxybenzoate (TINUVIN® 120); 4-bis(polyethoxy)amino acid polyethoxy ethyl ester (UVINUL® P 25); 4-t-butylphenyl 2-hydroxybenzoate, 2-hydroxy-4- octyloxybenzophenone (UVINUL® 3008); 2-hydroxy-4-methoxybenzophenone (UVINUL® 3040); 2-hydroxy-4-methoxy-5-sulfobenzophenone or sulisobenzone (UVINUL® MS 40); 2-(4-benzoyl-3-hydroxyphenoxy)-2-propenoic acid ethyl ester (CYASORB® UV 2098); homopolymer of 4-(2-acryloyloxyethoxy)-2- hydroxybenzophenone (CYASORB® UV 2126); 2,2'-dihydroxy-4- methoxybenzophenone or dioxybenzone (CYASORB® UV 24); 2-hydroxy-4-(2- hydroxy-3-decyloxypropoxy)benzophenone, 2-hydroxy-4-(2-hydroxy-3- octyloxypropoxy)benzophenone (MARK® 1535); 2,4,4'-trihydroxybenzophenone (MAXGARD® 200); 2-hydroxy-4-(isooctyloxy) benzophenone (MAXGARD® 800); 2- hydroxy-4-dodecyloxybenzophenone (UVINUL® 410); 2,2'-dihydroxy-4,4'-dimethoxy- 5,5'-disulfobenzophenone, disodium salt (UVINUL® 3048); 2,4- dihydroxybenzophenone (UVINUL® 400); 2,2'-dihydroxy-4,4'- dimethoxybenzophenone (UVINUL® D 49); 2,2',4,41-tetrahydroxybenzophenone (UVINUL® D 50); 2,2'-dihydroxy-4-(2-hydroxyethoxy)benzophenone (UVINUL® X-19); 2-hydroxy-4-benzyloxybenzophenone (SEESORB® 105); 2-hydroxy-4- hydroxybenzophenone, 2-hydroxy-4-decyloxybenzophenone, 2-hydroxy-4,2',4'- trihydroxybenzophenone, 2-hydroxy-4-(octyloxy)benzophenone (CHIMASSORB® 81 ); 2-hydroxy-2I-hydroxy-4,4'-dimethoxybenzophenone, 3,3' A', 5,7- pentahydroxyflavone, quercetin, 2-(2H-benzotriazol-2-yl)-6-dodecyl-4-methyl-phenol, methyl 3-(3-(2H-benzotriazole-2-yl)-5-t-butyl-4-hydroxyphenyl) propionate/PEG 300 (TINUVIN® 213); 6-tert-butyl-2-(5-chloro-2H-benzotriazole-2-yl)-4-methylphenol (UVINUL® 3026); 6-tert-butyl-2-(5-chloro-2H-benzotriazole-2-yl)-4-methylphenol (UVINUL® 3027); 2,4-di-tert-butyl-6-(5-chloro-2H-benzotriazole-2-yl)-phenol (UVINUL® 3028); 2-(2H-benzotriazole-2-yl)-4-(1 ,1 ,3,3-tetramethylbutyl)-phenol (UVINUL® 3029); 2-(2H-benzotriazole-2-yl)-4-methylphenol (UVINUL® 3033 P); 2- (2H-benzotriazole-2-yl)-4,6-bis(1-methyl-1-phenylethyl)phenol (UVINUL® 3034); 2-(2'- hydroxy-5'-(2-hydroxyethyl))benzotriazole (NORBLOC® 6000); 2-(2'-hydroxy-5'- methacrylyloxyethylphenyl)-2H-benzotriazole (NORBLOC® 7966); 1 ,1 ,1- tris(hydroxyphenyl) ethane benzotriazole (THPE BZT); 5-t-butyl-3-(5-chloro-2H- benzotriazol-2-yl)-4-hydroxybenzenepropanoic acid octyl ester, 3-(5-chloro-2H- benzotriazol-2-yl)-5-t-butyl-4-hydroxybenzenepropanoic acid octyl ester (TINUVIN® 109); a-[3-[3-(2H-benzotriazol-2-yl)-5-t-butyl-4-hydroxyphenyl]-1-oxopropyl]-w- hydroxypoly(oxy-1 ,2-ethane-diyl), a-[3-[3-(2H-benzotriazol-2-yl)-5-t-butyl-4- hydroxyphenyl]-1-oxopropyl]-w-[3-[3-(2H-benzotriazol-2-yl)-5-t-butyl-4- hydroxyphenyl]-1-oxopropoxy]poly(oxy-1 ,2-ethanediyl) (TINUVIN® 1130); 2-(2- hydroxy-3,5-di-t-butylphenyl) benzotriazole (TINUVIN® 320); 2-(2-hydroxy-3-t-butyl-5- methylphenyl)-5-chloro-2H-benzotriazole (TINUVIN® 326); 2-(3'-5'-di-t-butyl-2'- hydroxyphenyl-)-5-chlorobenzotriazole (TINUVIN® 327); 2-(2-hydroxy-3,5-di-t- amylphenyl)benzotriazole (TINUVIN® 328); 2-(2H-benzotriazol-2-yl)-4-(1 ,1 ,3,3- tetramethylbutyl)phenol (TINUVIN® 329); 3-(2H-Benzotriazol-2-yl)-5-t-butyl-4- hydroxybenzenepropanoic acid (TINUVIN® 384); 2-(2H-benzotriazol-2-yl)-4-methyl-6- dodecylphenol (TINUVIN® 571 ); 3-(2H-benzotriazol-2-yl)-5-t-butyl-4-hydroxy-1 ,6- hexanediyl ester of benzenepropanoic acid, 3-(2H-benzotriazol-2-yl)-5-t-but-yl-4- hydroxy-methyl ester of benzenepropanoic acid (Tl NUVI N® 840); 2-[2-hydroxy-3,5- bis-(1 ,1-dimethylbenzyl) phenyl]-2H-benzotriazole (TINUVIN® 900); 2-(2H- benzotriazol-2-yl)-6-(1-methyl-1-phenylethyl)-4-(1 ,1 ,3- ,3-tetramethylbutyl) phenol (TINUVIN® 928); 3-(2H-benzotriazol-2-yl)-5-t-butyl-4-hydroxybenzenepropanoic acid, C7-9 branched and linear alkyl esters (TINUVIN® 99); 2-(2H-benzotriazol-2-yl)-p- cresol (TINUVIN® P); 2-(2'-hydroxy-3'-sec-butyl-5'-t-butylphenyl) benzotriazole (TINUVIN® 350); 2-(2'-hydroxy-5'-t-butylphenyl) benzotriazole (TINUVIN® PS); 2,2'- methylenebis(6-(2H-benzotriazol-2-yl)-4-1 ,1 ,3,3-tetramethylbutyl)phenol (TINUVIN® 360); 2-(2H-benzo[d][1 ,2,3]triazol-2-yl)-4,6-bis(2-phenylpropan-2-yl)phenol (TINUVIN® 234); TINUVIN® B 75; 2,2'-(p-phenylene) di-3,1-benzoxazin-4-one (CYASORB® 3638); dimethyl(p-methoxybenzylidene)malonate (SANDUVOR® PR 25); 3-(4-methoxyphenyl)-2-propenoic acid 2-ethylhexyl ester, octyl p- methoxycinnamate, 3-(4-methylbenzylidene)-D,L-camphor (GIVSORB® UV-15); ethyl-4-[[(methylphenylamino)methylene]amino]benzoate (GIVSORB® UV-2, TINUVIN® 101 ); N-(2-ethoxyphenyl)-N'-(4-isododecylphenyl) oxamide (SANDUVOR® 3206); N-[5-t-butyl-2-ethoxyphenyl)-N'-(2-ethylphenyl) oxamide (TINUVIN® 315); N- (2-ethoxyphenyl)-N'-(2-ethylphenyl) oxamide (TINUVIN® 312); 2H-benzimidazole-2- carboxylic acid (4-ethoxyphenyl) amide (UVINUL® FK 4105); 4,4'-dioctyloxyoxanilide, 2,2'-diethoxyoxanilide, 2,2'-dioctyloxy-5,5'-di-tert-butoxanilide, 2,2'-didodecyloxy-5,5'- di-tert-butoxanilide, 2-ethoxy-2'-ethyloxanilide, N,N'-bis(3- dimethylaminopropyl)oxamide, 2-ethoxy-5-tert-butyl-2'-ethoxanilide, bis(2,2,6,6- tetramethyl-4-piperidyl)sebacate (TINUVIN® 770); N,N1-bis(2,2,6,6-tetramethyl-4- piperidyl)- N,N'-hexamethylenebis(formamide) (UVINUL® 4050H); polymer of 2,2,4,4-tetxamethyl-7-oxa-3,20-diaza-20-(2,3-epoxi-propyl)-dispiro-(5.1.11.2)- heneicosane-21-one (HOSTAVIN® N 30); bis(2,2,6,6-tetramethyl-1-(octyloxy)-4- piperidinyl) decanedioic acid ester (TINUVIN® 123); ester of [(4- methoxyphenyl)methylene]-, bis(1 ,2,2,6,6-pentamethyl-4-piperidinyl)propanedioic acid (SANDUVOR® PR-31 ); copolymer of dimethlylester of 4-hydroxy-2,2,6,6- tetramethyl-1-piperaidine ethanol butanedioic acid (TINUVIN® 622) and bis(2,2,6,6- tetramethyl-4-piperidyl)sebacate (TINUVIN® 783); 1 ,1I,1"-(1 I3I5-triazine-2,4l β- triyltris((cyclohexylimino)-2,1-eth- anediyl) ^5(3,3,4,5,5- pentamethylpiperazinone (GOODRITE® UV 3159); 1 ,6-Hexanediamine, N, N'-bis(2,2,6,6-tetramethyl-4- piperidinyl)-polymer with 2,4,6-trichloro-1 ,3,5-triazine, reaction products with N-butyl- 1-butanamine an N-butyl-2,2,6,6-tetramethyl-4-piperidinamine (CHIMASSORB® 2020); polymethylpropyl-3-oxy-4(2,2,6,6-tetramethyl)p- iperidinyl)siloxane (UVASIL® 299); bis(2,216,6-tetramethyl-4-piperidyl)succinate, bis(1 ,2,2,6,6-pentamethyl-4- piperidyl)sebacate, bis(1 -octyloxy-2,2,6,6-tetrannethyl-4-piperidyl)sebacate, poly[[6- [(1 ,1 ,3,3,-tetramethylbutyl)amino]-1 >3,5-triazine-2,4-diyl][(2,2,6,6-tetramethyl-4- piperidinyl)imino]-1 ,6-hexanediyl[(2,2,6,,6-tetramethyl-4-piperidinyl)imino]]) (CHIMASSORB® 944); bis(1 ,2,2,6,6-pentamethyl-4-piperidyl) n-butyl-3,5-di-tert- butyl-4-hydroxybenzylmalonate; the condensate of 1-(2-hydroxyethyl)-2, 2,6,6- tetramethyl-4-hydroxypiperidine and succinic acid; the condensate of N1N1- bis(2,2,6,6-tetramethyl-4-piperidyl)hexamethylenediamine and 4-tert-octylamino-2,6- dichloro-1 ,3,5-triazine, tris(2,2,6J6-tetramethyl-4-piperidyl)nitrilotriacetate; tetrakis(2,2,6I6-tetrannethyl-4-piperidyl)-1 ,2,3,4-butane-tetracarboxylate, 1 ,1 '-(1 ,2- ethanediyl)bis(3,3,5,5-tetramethylpiperazinone), 4-benzoyl-2, 2,6,6- tetramethylpiperidine, 4-stearyloxy-2l2,6,6-tetramethylpiperidine, bis(1 ,2,2,6,6- pentamethylpiperidyl)-2-n-butyl-2-(2-hydroxy-3,5-di-tert-butylbenzyl)malonate, 3-n- octyl-7,7,9,9-tetramethyl-1 ,3,8-triazaspiro[4.5]decan-2,4-dion, bis(1 -octyloxy-2,2,6,6- tetramethylpiperidyl)sebacate, bis(1-octyloxy-2,2,6,6-tetramethylpiperidyl)succinate, the condensate of N,N'-bis-(2,2,6,6-tetramethyl-4-piperidyl)hexamethylenediamine and 4-morpholino-2,6-dichloro-1 ,3,5-triazine; the condensate of 2-chloro-4,6-bis(4-n- butylamino-2,2,6,6-tetramethylpiperidyl)-1 ,3,5-triazine and 1 ,2-bis(3- aminopropylamino)ethane; the condensate of 2-chloro-4,6-di-(4-n-butylamino- 1 ,2,2,6,6-pentamethylpiperidyl)-1 ,3,5-triazine and 1 ,2-bis-(3- aminopropylamino)ethane; δ-acetyl-S-dodecyl-yj.θ.θ-tetramethyl-I .S.δ- triazaspiro[4.5]decane-2,4-dione, 3-dodecyl-1-(2,2,6,6-tetramethyl-4- piperidyl)pyrrolidin-2,5-dione, 3-dodecyl-1 -(1 ,2,2,6,6-pentamethyl-4- piperidyl)pyrrolidine-2,5-dione, a mixture of 4-hexadecyloxy- and 4-stearyloxy- 2,2,6,6-tetramethylpiperidine; a condensation product of N,N1-bis(2,2,6,6-tetramethyl- 4-piperidyl)hexamethylenediamine and 4-cyclohexylamino-2,6-dichloro-1 ,3,5-triazine; N-(2,2,6,6-tetramethyl-4-piperidyl)-n-dodecylsuccinimid, N-(1 ,2,2,6,6-pentamethyl-4- piperidyl)-n-dodecylsuccinimid, 2-undecyl-7,7,9,9-tetramethyl-1-oxa-3,8-diaza-4-oxo- spiro[4,5]decane, a reaction product of 7,7,9,9-tetramethyl-2-cycloundecyl-1-oxa-3,8- diaza-4-oxospiro [4,5]decane and epichlorohydrine, titanium dioxide, zinc oxide, zinc cerium oxide, carbon black, cadmium sulfide, cadmium selenide, chromium oxide, iron oxide, lead oxide, zirconium oxide, bis (1 , 2,2,6, 6-pentamethyl-4-piperidinyl)-2- butyl-2-(4-hydroxy-3,5-di-tert.-butylbenzyl)propanedioate (TINUVIN® 144); 4-t-butyl- 4'-methoxydibenzoylmethane, avobenzone (GIVSORB® UV-14); nickel dibutyldithiocarbamate; thio bis2,2'-[4-(1 ,1 ,3,3-tetramethylbutyl)-phenyl- ]nickel-2- ethyl hexanoate; n-butylamine-nickel-2,2'-thio bis(4-t-octylphenolate), nickel-bis-[2,2'- thio bis(4-t-octylphenolate)], octylphenyl salicylate, 4-t-butylphenylsalicylate (SEESORB® 202); S.S.δ-trimetylcyclohexylsalicylate or homomentyylsalicylate (NEO HELIOPAN HMS); menthyl-o-aminobenzoate (NEO HELIOPAN MA); 2-[4,6-bis(2,4- dimethylphenyl)-1 ,3,5-triazin-2-yl]-5-octyloxyphenol (CYASORB® UV 1164); confidential triazine derivative (TINUVIN® 1545); 2-(4J6-diphenyl-1 ,3,5-triazin-2-yl)-5- hexyloxyphenol (TINUVIN® 1577 FF); 2-[4-((2-hydroxy-3-dodecyloxypropyl)oxy)-2- hydroxyphenyl]-4,6-bis(2,4-dimethylphenyl)-1 ,3,5-triazine (TINUVIN® 400); 2,4,6- Trianilino-p-fcarbo^'-ethylhexyM'-oxy)-! ,3,5-triazine (UVINUL® T-150); 2, 4-bis(2, 4- dihydroxyphenyl)-6-(1 -methyl-1 H-pyrazol-5-yl)-1 ,3,5-triazine, 2,4-bis{[4-(2- ethylhexyloxy)-2-hydroxy]phenyl}-6-(1-methyl-1 H-pyrazol-5-yl)-1 ,3,5-triazine, 2-[2, 4- bis (2-ethylhexyloxy)phenyl]-4-[4-(2-ethylhexyloxy)-2-hydroxyphenyl]-6-(1 -methyl-1 H- pyrazol-5-yl)-1 ,3,5- triazine, 2,4-bis(2, 4-dihydroxyphenyl)-6(1-phenyl-1 H-pyrazol-5- yl)-1 ,3,5-triazine, 2,4-bis{[4-(2-ethylhexyloxy)-2-hydroxy]phenyl}-6-(1-phenyl-1 H- pyrazol-5-yl)-1 ,3,5-triazine, 2,4-bis [4-(butoxycarbonyl)phenylamino]-6-(1 -methyl-1 H- pyrazol-5-yl)-1 ,3,5-triazine, 2,4-bis{4-[(2-(ethylhexyloxy)carbonyl]phenylamino}-6-(1 - methyl-1 H-pyrazol-5-yl)-1 ,3,5-triazine, 2,4-bis [4-(butoxycarbonyl)phenylamino]-6-(1 - phenyl-1 H-pyrazol-5-yl)-1 ,3,5-triazine, 2,4-bis{4-[(2- ethylhexyloxy)carbonyl]phenylamino}-6-(1-phenyl-1 H-pyrazol-5-yl)-1 ,3,5-triazine, 2- [(4-butoxycarbonyl)phenylamino]-4,6-bis(1 -methyl-1 H-pyrazol-5-yl)-1 ,3,5-triazine, 2- (1-benzyl-1 H-pyrrol-2-yl)-4,6-bis(2,4-dihydroxyphenyl)-1 ,3,5-triazine, 2-(1-benzyl-1 H- pyrrol-2-yl)-4,6-bis[4-(2-ethylhexyloxy)-2-hydroxyphenyl]-1 ,3,5-triazine, 2-(1 -benzyl- 1 H-pyrrol-2-yl)-4,6-bis[4-(butoxycarbonyl) phenylamino]-1 ,3,5-triazine, 2-(1-benzyl- 1 H-pyrrol-2-yl)-4,6-bis(biphenyl-4-ylamino)-1 ,3,5-triazine, 2-(1-benzyl-1 H-pyrrol-2-yl)- 4,6-bis(4-benzoylphenylamino)-1 ,3,5-triazine, 2-(1-benzyl-1 H-pyrrol-2-yl)-4,6-bis(9- oxo-9H-fluoren-3-ylamino)-1 ,3,5-triazine, 2-(1-benzyl-1 H-pyrrol-2-yl)-4,6-bis[4- (imidazo[1 ,2-a]pyridin-2-yl)phenylamino]-1 ,3,5-triazine, 2-(1-benzhydryl-1 H-pyrrol-2- yl)-4,6-bis[4-(butoxycarbonyl)phenylamino]-1 ,3,5-triazine, 2-(1-benzyl-1 H-pyrrol-2-yl)- 4, 6-bis[4-(6,6-dimethyl-4-oxo-4,5,6,7-tetrahydroindol-1-yl)phenylamino]-1 ,3,5-triazine, 2-(1 -benzyl-1 H-pyrrol-2-yl)-4,6-bis[4-((2-ethylhexyloxy)carbonyl)phenylamino]-1 ,3,5- triazine, 2-(1-benzyl-1 H-pyrrol-2-yl)-4,6-bis[4-1 H-imidazo[1 ,2-a]pyridin-2- yl)phenylamino]-1 ,3,5-triazine, 2-(1 -benzyl-1 H-pyrrol-2-yl)-4,6-bis[4-(1 H- benzo[d]imidazol-2-yl)phenylamino]-1 ,3,5-triazine, 2-(1-benzyl-1 H-pyrrol-2-yl)-4,6- bis[4-(1 H-pyrazol-1-yl)phenylamino]-1 ,3,5-triazine, 2-(1-benzyl-1 H-pyrrol-2-yl)-4,6- bis[naphthalen-2-ylamino]-1 ,3,5-triazine, 2-(1-benzyl-1 H-pyrrol-2-yl)-4,6-bis[4-((E)-3- ethoxy-3-oxoprop-1-enyl)phenylamino]-1 ,3,5-triazine and 2-(1-benzyl-1 H-pyrrol-2-yl)- 4,6-bis[4-(E)-styrylphenylamino]-1 ,3,5-triazine;
and/or at least one of the stereoisomers, preferably enantiomers or diastereomers, a racemate or a mixture of at least two of the stereoisomers, preferably enantiomers and/or diastereomers in any mixing ratio, or at least one physiologically acceptable salt and/or at least one corresponding solvate of the aforementioned compounds;
and/or
at least one compound selected from the group comprising 2-ethylhexyl 2-cyano-3,3'- diphenylacrylate, ethyl 2-cyano-3,3'-diphenylacrylate, polymer of N-{(2 and 4)[(2- oxoborn-3-ylidene)methyl]benzyl}acrylamide, methyl 4-aminobenzoate, butyl 4- aminobenzoate, 5-methyl-2-(1-methylethyl)-cyclohexyl 2-aminobenzoate, glyceryl aminobenzoate, 2-ethylhexyl-p-dimethylethyl-aminobenzoate, 4-aminobenzamide, homomethyl-N-acetyl-anthranilic acid, menthyl antrhanilate, 2-(1 H-benzimidazol-2- yl)-4-methoxyphenol, 2,2'-bis(benzimidazole), monosodium salt of 2-2'-bis-(1 ,4- phenylene)1 H-benzimidazole-4,6-disulphonic acid, 2-phenylbenzimidazole-5- sulphonic acid, 5,5',6,6'-tetramethyl-2,21-bis(benzimidazole), 5,5'-dimethyl-2,2'- bis(benzimidazole), 6-methoxy-2,2'-bis(benzimidazole), 1 ,4-phenylenebis(2- benzimidazolyl), 1 ,2-phenylenebis)benzimidazolyl), 1 ,4-phenylenebis(N-2-ethylhexyl- 2-benzimidazolyl), 1 ,4-phenylenebis(N-tri-methylsilylmethyl-2-benzimidazolyl), 2-(1 H- benzimidazol-2-yl)benzothiazole, 2-(1 H-benzimidazol-2-yl)benzoxazole, N1N1- dimethyl-2,21-bis(benzimidazole), phenylbenzimidazole-5-sulfonic acid (Ensulizole) and its salts , 2-2'-bis-(1 ,4-phenylene)1 H-benzimidazole-4,6-disulphonic acid, 3-me- thylbutyl 4-(dimethylamino)benzoate, 3,3,5-trimethylcyclohexyl 2-hydroxybenzoate (Homosalate), ethyl 4-aminobenzoate, 4,4-((6-(((1 ,1-di- methylethyl)amino)carbonyl)phenyl)amino) 1 ,3,5-triazine-2,4-diyl)diimino)bis-,bis-(2- ethyl-hexyl)ester) benzoic acid, 2,4-dihydroxy-benzophenone (Benzophenone-1 ), 2,2'-dihydroxy-4-methoxy-benzophenone (dioxybenzone, Benzophenone-8), 2,2'- dihydroxy-4,4'-dimethoxy-benzophenone, 2,2',4,4'-tetrahydroxy-benzophenone, 2- hydroxy-4-methoxy-4'-methyl-benzophenone, hydroxymethoxy-benzophenone sulfonic acid, (2-hydroxy-4-methoxyphenyl)-phenylmethanone (Benzophenone-3), 2- hydroxy-4-methoxy-benzophenone-5-sulfonic acid (Benzophenone-4) and its salts, 4- phenyl-benzophenone, 2-ethylhexyl-4'-phenyl-benzophenone-2-carboxylate, 2- hydroxy-4-n-octoxy-benzophenone, 4-hydroxy-3-carboxy-benzophenone, 4-(2-β- glucopyranosiloxy)-propoxy-2-hydroxybenzophenone, dihydroxy-dimethoxy-di- sulfobenzophenone, 2-benzothiazol-2-ylphenol, [2,4'-dihydroxy-3-(2H-benzotriazol-2- yl)-5-(1 ,1.S.S-tetramethylbutyO^'-n-octoxy-S'-benzoyll-diphenylmethane, 2,2'- hydroxy-5-methylphenyl-benzotriazole, 2-(2'-hydroxy-5'-t-octylphenyl)benzotriazole, 2-(21-hydroxy-5'-methylphenyl)benzotriazole, 2,2'-methylene-bis-6-(2H-benzotriazol- 2-yl)-4-(tetramethyl-butyl)-1 ,1 ,3,3-phenol, 2-benzoxazole-2-yl-4-methylphenol, 2- phenyl-5-methylbenzoxazole, 1 ,4-phenylenebis(2-benzoxazolyl), 1 ,3-phenylenebis(2- benzoxazolyl), 1 ,2-phenylenebis(2-benzoxazolyl), 2-(2-benzofuryl)-benzoxazole, 2- (benzofuryl)-5-methylbenzoxazole, 2-(3-methyl-2-benzofuryl)benzoxazole, 3-(4'- methylbenzylidene)-D,L-camphor, terephthalylidene dicamphor sulphonic acid, 3- benzylidene-D,L-camphor, 4-benzylidene-D,L-camphor, di-tert-butyl hydroxybenzylidene camphor, benzylidene camphor sulphonic acid, camphor benzalkonium methosulfate, polyacrylamido-methyl benzylidene camphor, ethylhexyl methoxycinnamate, diethanolamine p-methoxy cinnamate, isopropyl-p-acetamido cinnamate, octyl cinnamate, ethyl-4-isopropylcinnamate, methyl-2,5-diisopropyl cinnamate, ethyl-2,4-diisopropylcinnamate, methyl-2,4-diisopropylcinnamate, propyl- p-methoxycinnamate, isopropyl-p-methoxycinnamate, diisopropylcinnamate esters, isoamyl-p-methoxycinnamate, cyclohexyl-p-methoxycinnamate, ethyl-α-cyano-β- phenylcinnamate, 2-ethylhexyl-α-cyano-β-phenylcinnamate, glycerin-mono-2-ethyl- hexanoyl-diparamethoxycinnamate, glyceryl octanoate-di-p-methoxycinnamate, DEA- methoxycinnamate, methyl-bis(trimethyl-siloxy)silyl-isopentyl-trimethoxycinnamate, ethyl-α-cyano-3,5-dimethoxy-4-hydroxy cinnamate, ethyl-α-acetyl-3,5-dimethoxy-4- hydroxy cinnamate, iso-propyl-α-acetyl-3,5-dimethoxy-4-hydroxy cinnamate, iso- amyl-α-acetyl-3,5-dimethoxy-4-hydroxy cinnamate, 2-ethylhexyl-α-acetyl-3,5- dimethoxy-4-hydroxy cinnamate, ethyl-α-cyano-3-methoxy-4-hydroxy cinnamate, ethyl-α-acetyl-3-methoxy-4-hydroxy cinnamate, iso-propyl-α-acetyl-3-methoxy-4- hydroxy cinnamate, iso-amyl-α-acetyl-S-methoxy^-hydroxy cinnamate, 2-ethylhexyl- α-acetyl-3-methoxy-4-hydroxy cinnamate, 7-ethylamino-4-methylcoumarin, 7,8- dihydroxycoumarin, 6,7-dihydroxycoumarin, 7-hydroxycoumarin, 4-methyl-7- hydroxycoumarin, diacetycurcumin, tetrahydrocurcumin diacetate, dianisoylmethane, dibenzalazine, butyl methoxydibenzoylmethane (Avobenzone), 2- methyldibenzoylmethane, 4-methyldibenzoylmethane, 4-isopropyldibenzoylmethane, 4-tert-butyldibenzoylmethane, 2,4-dimethyldibenzoylmethane, 2,5- dimethyldibenzoylmethane, 4,4'-diisopropyldibenzoylmethane, 4,4'- dimethoxydibenzoylmethane, 2-methyl-5-isopropyl-4'-methoxydibenzoylmethane, 2- methyl-5-tert-butyl-4'-methoxydibenzoylmethane, 2,4-dimethyl-4'- methoxydibenzoylmethane, 2,6-dimethyl-4-tert-butyl-4'-methoxydibenzoylmethane, ferulic acid, dimethicodiethylbenzalmalonate, diethyl-3,5-dimethoxy-4-hydroxy benzylidene malonate, di-(2-ethylhexyl)-3,5-dimethoxy-4-hydroxy benzylidene malonate, diisoamyl-3,5-dimethoxy-4-hydroxy benzylidene malonate, didodecyl-3,5- dimethoxy-4 hydroxy benzylidene malonate, dipalmitoyl-3,5-dimethoxy-4-hydroxy benzylidene malonate, di-isopropyl-3,5-dimethoxy-4-hydroxy benzylidene malonate, diethyl-3-methoxy-4-hydroxy benzylidene malonate, di-(2-ethylhexyl)-3-methoxy-4- hydroxy benzylidene malonate, diisoamyl-3-methoxy-4-hydroxy benzylidene malonate, didodecyl-3-methoxy-4-hydroxy benzylidene malonate, dipalmitoyl-3- methoxy-4-hydroxy benzylidene malonate, di-isopropyl-3-methoxy-4-hydroxy benzylidene malonate, hydrolyzed aspergillus sp. extract ferment, 4-nitrobenzamide, 4-nitrobenzoic acid, p-aminobenzoic acid (PABA), PABA-monoglycerinester, N1N- dipropoxy-PABA-ethylester, N,N-diethoxy PABA-ethylester, N,N-dimethyl PABA- ethylester, N,N-dimethyl PABA-butylester, PEG-25 PABA, N,N-dimethyl PABA- amylester, N,N-dimethyl PABA-octlylester (2-ethylhexyl 4-(dimethylamino)benzoate, Padimate O), octyl dimethyl PABA, ethyl-dihydroxypropyl-PABA, isoamyl dimethyl PABA (3-methylbutyl 4-(dimethylamino)benzoate, Padimate A), 1-(3,4- dimethoxyphenyl)-4,4-diemthyl-1 ,3-pentanedione, 5-(3,3-Dimethyl-2-norbornyliden)- 3-pentane-2-one, 1 -(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1 ,3-dione, dipropylene glycol salicylate, 2-ethylhexyl 2-cyano-3,3-diphenyl-2-propenoate (Octocrylene), hydrolyzed soy extract, hydrolyzed linseed extract, sunflower seed extract, grape seed extract, pinus pinaster bark extract, pinus pinaster bud extract, ginseng extract ferment, spirulina platensis powder, p-tert-butylphenyl salicylate, p- octylphenyl salicylate, 2-ethylhexyl salicylate (octyl salicylate), amyl salicylate, menthyl salicylate, homomenthyl salicylate, benzyl salicylate, p-isopropanol-phenyl salicylate, TEA-salicylate, 2-(2H-benzotriazol-2-yl)-4-methyl-6-[2-methyl-3-[1 ,3,3,3- tetramethyl-1-[(trimethylsilyl)oxy]disiloxanyl]propyl]-phenol (Mexoryl XL), 2-[p-(tert- butylamido)anilino]-4,6-bis[p-(2'-ethylhexyl-1 '-oxycarbonyl)anilino]-1 ,3,5-triazine (INCI name: Diethylhexyl Butamido Triazone), 2,4,6-tris[4-(2-ethylhexyl-oxycarbonyl)- anilino]-1 ,3,5-triazine (INCI name: Ethylhexyl Triazone), (1 ,3,5)-triazine-2,4-bis((4-2- ethyl-hexyloxy)-2-hydroxy)-phenyl)-6-(4-methoxy-phenyl) (bemotrizinol), octyl triazone (CAS-no.: 88122-99-0), , urocanic acid, ethyl-urocanic acid, talc, kaolin, calcium carbonate, bisoctrizole (CAS-no.: 103597-45-1), bornelone (CAS-no.: 2226- 11-1 ), 2-hydroxy-1 ,4-naphthochinone (Lawsone, CAS-no.: 83-72-7), petrolatum red, phenol sulphonate, sodium 3,4-dimethylphenyl-glyoxylate, 3,3'-(1 ,4- phenylenedimethylene-bis-(7,7-dimethyl-2-oxobicyclo-[2,2,1]hept-1-yl- methanesufonic acid, α-(2-oxoborn-3-ylidene)-toluene-4-sulphonic acid, 2-(2H- benzotriazole-2-yl)-4-methyl-6-[2-methyl-3-[1 ,3,3,3-tetramethyl-1- [(trimethylsilyl)oxy]disiloxanyl]propyl]-phenol (INCI name: drometrizole trisiloxane, DTS), digalloyl trioleate, dimethicone/PEG-15 crosspolymer, ethylhexyl-bis-isopentyl- benzoxazolyl-phenyl melamine and 2-ethylhexyl-dimethoxy-benzylidene-dioxo- imidazolidine propionate;
and/or at least one of the stereoisomers, preferably enantiomers or diastereomers, a racemate or a mixture of at least two of the stereoisomers, preferably enantiomers and/or diastereomers in any mixing ratio, or at least one physiologically acceptable salt and/or at least one corresponding solvate of the aforementioned compounds.
In a preferred embodiment of the present invention, the aforementioned further light stabilizers (Z) of the inventive light-stabilizing component are already known as stabilizers.
The inventive composition comprises preferably 0.001 to 25 % by weight, more preferably 0.01 to 25% by weight, most preferably 0.05 to 10% by weight, based on the total weight of the composition, of the light-stabilizing component.
In a preferred embodiment of the present invention, at least one of the light stabilizers of the inventive light-stabilizing component absorbs light in a wavelenth range from 100 to 700 nm, more preferably from 290 to 700 nm, most preferably from 290 to 400 nm. The term "absorption" according to the present invention means any of the following ways of reducing the exposure to light radiation, like absorbing, extincting, filtering, scattering, deflecting or reflecting of light radiation, since absorption only means the ratio of transmitted radiation to the incident radiation, without determining the mechanism according to which the light radiation is reduced.
In another preferred embodiment of the present invention, at least one light stabilizer of the inventive light-stabilizing component absorbs light in the range of UV-A (320 to 400 nm) and/or in the UV-B (290 to 320 nm) radiation.
In another preferred embodiment of the present invention, at least one light stabilizer of the inventive light-stabilizing component has a melting point >50°C, more preferably >100°C, more preferably >150°C, most preferably >200°C. In another preferred embodiment of the present invention the melting point for light stabilizers suitable for thermoplastic polymers is >100°C, more preferably >200°C.
Polymers can be preferably classified into four main groups:
1. Thermoplastic polymers
2. Thermosetting polymers/thermosets
3. Elastomers
4. Coordination polymers
1. Thermoplastic polymers
Plastics made of thermoplastic polymers is deformable, melts to a liquid when heated and freezes to a brittle, glassy state when cooled sufficiently. Most thermoplastic polymers are high molecular weight polymers whose chains associate through weak van der Waals forces (polyethylene), stronger dipole-dipole interactions and hydrogen bonding (nylon) or even stacking of aromatic rings (polystyrene). Thermoplastic polymers can not be remelted and remolded.
2. Thermosetting polymers
Thermosetting polymers ("thermosets") are materials that cure, through the addition of energy, to a stronger form. The energy may be in the form of heat (generally above 2000C), through a chemical reaction (two-part epoxy, for example), or irradiation. Thermoset materials are usually liquid, powder, or malleable prior to curing, and designed to be moulded into their final form, or used as adhesives. The curing process transforms the resin into a plastic or rubber by a cross-linking process. Energy and/or catalysts are added that cause the molecular chains to react at chemically active sites (unsaturated or epoxy sites, for example), linking into a rigid, 3-D structure. The cross-linking process forms a molecule with a larger molecular weight, resulting in a material with a higher melting point. During the reaction, when the molecular weight has increased to a point so that the melting point is higher than the surrounding ambient temperature, the material forms into a solid material. Subsequent uncontrolled reheating of the material results in reaching the decomposition temperature before the melting point is obtained. A thermoset material cannot be melted and re-shaped after it is cured. Thermoset materials are generally stronger than thermoplastic materials due to this 3-D network of bonds and are also better suited to high-temperature applications up to the decomposition temperature of the material.
3. Elastomers
The term elastomer is often used interchangeably with the term rubber, and is preferred when referring to vulcanisates. They are amorphous polymers existing above their glass transition temperature, so that considerable segmental motion is possible. At ambient temperatures rubbers are thus relatively soft and deformable. Their primary uses are for seals, adhesives and molded flexible parts. 4. Coordination polymers
Coordination polymers are compounds where the metals are bridged by polyatomic ligands, such as e.g. cyanide or carboxylates.
In a preferred embodiment of the present invention, the polymer is at least one polymer selected from the group comprising thermoplastic polymers, thermosetting polymers, elastomers and/or coordination polymers.
In a further preferred embodiment of the present invention, the thermoplastic polymer is at least one polymer selected from the group comprising acrylonitrile-butadiene- styrene (ABS) copolymer; cellulose derivatives such as cellulose acetate, cellulose acetate propionate, cellulose acetate butyrate, cellulose triacetate, cellulose ether, methylcellulose, ethylcellulose, propylcellulose, hydroxyethylcellulose, hydroxypropyl- cellulose, hydroxypropylmethylcellulose and carboxy methylcellulose; ethylene-vinyl acetate (EVA) copolymer; ethylene vinyl alcohol (EVAL) copolymer; polyolefines such as ethylen-propylen copolymer, ethylene-buten-1 copolymer, ethylene-hexene copolymer, ethylene-methylpentene copolymer, ethylene-heptene copolymer, ethylene octene copolymer, polybutylene (PB), polymethylpentene (PMP), polypropylene (PP) and polyethylene (PE) such as low density polyethylene (LDPE), linear low density polyethylene (LLDPE), high density polyethylene (HDPE) and metallocene-PE (mPE); ethylen-alkylacrylate copolymer such as ethylen- ethylacrylate copolymer; ethylene-alkylmethylacrylate copolymer; fluoro resins such as polytetrafluoroethylene (PTFE) or perfluoro (ethylene-propylene) copolymer (FEP); chloro-trifluoroethylene (CTFE), ethylene-chlorotrifluoroethylene (ECTFE); ethylene-tetrafluorethylene copolymer (ETFE) and tetrafluoroethylene-propylene copolymer; ionomer; liquid crystal polymer (LCP); polyacetal; polyacrylate; polymethacrylate; polyacrylonitrile; polyamide (PA); polyamide-imide; polyesters such as polybutylene terephthalate (PBT), polyethylene terephthalate (PET) and polycyclohexylene dimethylene terephthalate (PCT); polycarbonate (PC); polyhydroxyalkanoate; polyketone (PK); polyetheretherketone (PEEK); polyetherimide (PEI); polyethersulfone (PES); polyimide (Pl); polylactic acid (PLA); polyphenylene oxide (PPO); polyphenylene sulfide (PPS); polyphthalamide (PPA); homo- or copolymers of styrene such as e.g. styrene-isopren-styrene block copolymer; polysulfone (PSU); polyurethane (PU); polyvinyl ether; polyvinylalcohol; polyvinylidenechloride; polyvinylpyrrolidone; polyvinyl chloride (PVC); vinyl chloride- vinyl acetate copolymer; vinyl chloride-vinylidene dichloride copolymer and vinyl pyrrolidon-ethylen-vinylacetate copolymer.
In a further preferred embodiment of the present invention, the thermosetting polymer is at least one polymer selected from the group comprising vulcanized rubber; polyoxybenzylmethylenglycolanhydride; duroplast; urea-formaldehyde resins; melamine; cured polyester resins and epoxy resins.
In a further preferred embodiment of the present invention, the elastomer is at least one polymer selected from the group comprising homo-, co- or block polymer of butadiene; natural rubber (NR); polyisoprene (IR); butyl rubber; halogenated butyl rubbers such as chloro butyl rubber or bromo butyl rubber; polybutadiene (BR); styrene-butadiene rubber (SBR); nitrile rubber; hydrated nitrile rubbers (HNBR); chloroprene rubber (CR); polychloroprene; neoprene; ethylene propylene rubber (EPM); ethylene propylene diene rubber (EPDM); epichlorohydrin rubber (ECO); polyacrylic rubber; silicone rubber; silicone; silcone derivatives such as siloxane- methacrylate polymers; fluorosilicone rubber; fluoroelastomers; perfluoroelastomers (FFKM); tetrafluoro ethylene/propylene rubbers (FEPM); chlorosulfonated polyethylene (CSM); ethylene-vinyl acetate (EVA) copolymers; thermoplastic elastomers (TPE); polyurethane rubber and polysulfide rubber.
Polymer compositions usually comprise additives, which improve the properties of these compositions. Suitable additives used in the inventive light-stabilized composition preferably include, but are not limited to anti-blocking-agents, anti- fogging agents, antistatic agents, antioxidants, biocides, blowing agents, defoamers, dyes, emulsifiers, fillers, flame retardants, heat stabilizers, impact modifiers, lubricants, metal deactivators, hydrocalcites, mould-release agents, optical brighteners, plastisizers, processing agents, pigments, phosphites, phosphonites, reinforcing agents, rheology additives, slip agents and surfactants, whereby each of these aforementioned additives is used in usual amounts known by those skilled in the art. In a preferred embodiment of the present invention the inventive light-stabilized composition is in form of a painting, a coating, textile fibers or granulate.
The light-stabilizing component can be mixed with the preferably mulitparticular polymer, preferably powder or granulate, in order to prepare an inventive light- stabilized composition. Preferably, such composition is prepared by premixing part of the polymer and the light stabilizer component to obtain a master batch, which is finally mixed with the residue of the polymer in order to achieve a homogeneous distribution of the light stabilizer component in the polymer.
The articles, moulds, sheets, foils, paintings, coatings, fibers or films, are manufactured by techniques known by those skilled in the art, using the inventive light-stabilized composition as raw material.
A further aspect of the present invention refers to articles, moulds, sheets, foils, paintings, coatings, fibers or films, which are produced of the inventive light-stabilized composition described above. The films produced of the inventive light-stabilized composition are single-layer or multilayer films, which can be used for medical or agricultural applications.
The articles, moulds, sheets, foils or films, which are produced of the inventive light- stabilized composition described above are preferably suitable for outdoor carpeting, awnings, tarps, umbrellas, non-food or food-packaging applications such as rice, corn and flour bags, tapes, ropes, artificial turf, stretch-films, shrink wraps, heavy-duty bags, pool covers, garden furniture, trash cans, bottle and fruit crates, toys, interior and exterior automotive parts such as auto bumbers and interior or exterior trim, outdorr sporting and leisure goods, roofings and window shutters.
A further aspect of the present invention refers to the use of at least one heptaazaphenalene compound as defined above in an amount of 0.01 to 25 % by weight, based on the total weight of the composition, as a light-stabilizing component for polymers. A further aspect of the present invention refers to the use of a combination comprising at least one heptaazaphenalene compound as defined above in an amount of 0.01 to 25 % by weight, based on the total weight of the composition and at least one further light-stabilizing compound (Z) selected from the group comprising acrylate derivatives, allantoin derivatives, aminobenzoic acid derivatives, aminobenzamides derivatives, anthranilic acid derivatives, benzalmalonic acid derivatives, benzimidazole derivatives, benzoate derivatives, benzophenone derivatives, benzopyranone derivatives, benzothiazole derivatives, benzotriazole derivatives, benzoxazinone derivatives, benzoxazole derivatives, camphor derivatives, cinnamate derivatives, coumarinic acid derivatives, curcumin derivatives, cycloaliphatic ketone derivatives, dianisoylmethane derivatives, dibenzalazine derivatives, dibenzoylmethane derivatives, dioxane derivatives, ferulic acid derivatives, formamidine derivatives, formanilides, furane derivatives, glutamic acid derivatives, hindered amine derivatives, imidazoline derivatives, inorganic pigments, malonic acid derivatives, metal oxides, metal dioxides, nicotinic acid derivatives, nitrobenzamides derivatives, nitrobenzoic acid derivatives, nucleic acid derivatives, oxamide derivatives, oxanilide derivatives, p-aminobenzoic acid (PABA) derivatives, plant extracts, aromatic propanedione derivatives, propenoate derivatives, pyrimidine derivatives, quenchers, salicylate derivatives, tetrazole derivatives, triazine derivatives, tributamine derivatives, urocanic acid derivatives and vitamin B6 derivatives as light-stabilizing component for polymers.
Another preferred embodiment of the present invention refers to the use of a combination comprising at least one heptaazaphenalene compound as defined above and at least one further light stabilizer (Z) compound of general formulae (X), (Is), (L1 ), (L2), (L3), (L4), (L5), (L6), (L7), (L8), (L9), (L10), (L11 ), (L12), (L13) and/or (L14) as defined above, in an amount of 0.01 to 25 % by weight, based on the total weight of the composition.
Another preferred embodiment of the present invention refers to the use of a combination comprising at least one heptaazaphenalene compound as defined above and at least one further light stabilizer (Z) selected from the group comprising α-cyano-β, β-di-phenylacrylate, methyl α-carbomethoxycinnamate, methyl α-cyano-β- methyl-p-methoxycinnamate, butylα-cyano-β-methyl-p-methoxy-cinnamate, methyl α- carbomethoxy-p-methoxycinnamate, N-(β-carbomethoxy-β-cyanovinyl)-2- methylindoline, ethyl-2-cyano-3,3-diphenylacrylate (UVINUL® 3035); 2-ethylhexyl-2- cyano-3,3-diphenylacrylate (UVINUL® 3039); 1 ,3-bis-[(2'-cyano-3,3'- diphenylacryloyl)oxy]-2,2-bis-{[(2-cyano-3',3'-di- phenylacryloyl)oxy]methyl}propane (UVINUL® 3035); 2-cyano-3-(2-methylindolin- yl) methylacrylate (UV Absorber Bayer 340); 2-phenyl-1 H-benzimidazole-5-sulfonic acid (GIVSORB® UV-16); dibenzoyl resorcinol, bis(4-tert-butylbenzoyl) resorcinol, benzoyl resorcinol, 2,4-di- tertbutylphenyl 3,5-di-tert-butyl-4-hydroxybenzoate, hexadecyl 3,5-di-tert-butyl-4- hydroxybenzoate, octadecyl 3,5-di-tert-butyl-4-hydroxybenzoate, 2-methyl-4,6-di-tert- butylphenyl 3,5-di-tert-butyl-4-hydroxybenzoate, hexadecyl 3 , 5-d i-t-butyl-4- hydroxybenzoate (CYASORB® UV 2908); 3-hydroxyphenylbenzoate (SEESORB® 300); ethyl-4-[[(ethylphenylamino)methylene]amino]benzoate (GIVSORB® UV-1 ); phenyl 2-hydroxybenzoate or phenylsalicylate (SEESORB® 201 ); 2,4-di-t- butylphenyl-3,5-di-t-butyl-4-hydroxybenzoate (TINUVIN® 120); 4- bis(polyethoxy)amino acid polyethoxy ethyl ester (UVINUL® P 25); 4-t-butylphenyl 2- hydroxybenzoate, 2-hydroxy-4-octyloxybenzophenone (UVINUL® 3008); 2-hydroxy-4- methoxybenzophenone (UVINUL® 3040); 2-hydroxy-4-methoxy-5- sulfobenzophenone or sulisobenzone (UVINUL® MS 40); 2-(4-Benzoyl-3- hydroxyphenoxy)-2-propenoic acid ethyl ester (CYASORB® UV 2098); homopolymer of 4-(2-acryloyloxyethoxy)-2-hydroxybenzophenone (CYASORB® UV 2126); 2,2'- dihydroxy-4-methoxybenzophenone or dioxybenzone (CYASORB® UV 24); 2- hydroxy-4-(2-hydroxy-3-decyloxypropoxy)benzophenone, 2-hydroxy-4-(2-hydroxy-3- octyloxypropoxy)benzophenone (MARK 1535); 2,4,41-trihydroxybenzophenone (MAXGARD® 200); 2-hydroxy-4-(isooctyloxy) benzophenone (MAXGARD® 800); 2- hydroxy-4-dodecyloxybenzophenone (UVINUL® 410); 2,2l-dihydroxy-4,4'-dimethoxy- δ.δ'-disulfobenzophenone, disodium salt (UVINUL® 3048); 2,4- dihydroxybenzophenone (UVINUL® 400); 2,2'-dihydroxy-4,41- dimethoxybenzophenone (UVINUL® D 49); 2,2',4I4I-tetrahydroxybenzophenone (UVINUL® D 50); 2,2'-dihydroxy-4-(2-hydroxyethoxy)benzophenone (UVINUL® X-19); 2-hydroxy-4-benzyloxybenzophenone (SEESORB® 105); 2-hydroxy-4- hydroxybenzophenone, 2-hydroxy-4-decyloxybenzophenone, 2-hydroxy-4,2',41- trihydroxybenzophenone, 2-hydroxy-4-(octyloxy)benzophenone (CHIMASSORB® 81 ); 2-hydroxy-21-hydroxy-4)4'-dimethoxybenzophenone, 3,3',4',5,7- pentahydroxyflavone, quercetin, 2-(2H-benzotriazol-2-yl)-6-dodecyl-4-methyl-phenol, methyl 3-(3-(2H-benzotriazole-2-yl)-5-t-butyl-4-hydroxyphenyl) propionate/PEG 300 (TINUVIN® 213); 6-tert-butyl-2-(5-chloro-2H-benzotriazole-2-yl)-4-methylphenol (UVINUL® 3026); 6-tert-butyl-2-(5-chloro-2H-benzotriazole-2-yl)-4-methylphenol (UVINUL® 3027); 2,4-di-tert-butyl-6-(5-chloro-2H-benzotriazole-2-yl)-phenol (UVINUL® 3028); 2-(2H-benzotriazole-2-yl)-4-(1 ,1 ,3,3-tetramethylbutyl)-phenol (UVINUL® 3029); 2-(2H-benzotriazole-2-yl)-4-methylphenol (UVINUL® 3033 P); 2- (2H-benzotriazole-2-yl)-4,6-bis(1-methyl-1-phenylethyl)phenol (UVINUL® 3034); 2-(2'- hydroxy-5'-(2-hydroxyethyl))benzotriazole (NORBLOC® 6000); 2-(2'-hydroxy-5'- methacrylyloxyethylphenyl)-2H-benzotriazole (NORBLOC® 7966); 1 ,1 ,1- tris(hydroxyphenyl) ethane benzotriazole (THPE BZT); 5-t-butyl-3-(5-chloro-2H- benzotriazol-2-yl)-4-hydroxybenzenepropanoic acid octyl ester, 3-(5-chloro-2H- benzotriazol-2-yl)-5-t-butyl-4-hydroxybenzenepropanoic acid octyl ester (TINUVIN® 109); a-[3-[3-(2H-benzotriazol-2-yl)-5-t-butyl-4-hydroxyphenyl]-1 -oxopropyl]-w- hydroxypoly(oxy-1 ,2-ethane-diyl), a-[3-[3-(2H-benzotriazol-2-yl)-5-t-butyl-4- hydroxyphenyl]-1-oxopropyl]-w-[3-[3-(2H-benzotriazol-2-yl)-5-t-butyl-4- hydroxyphenyl]-1-oxopropoxy]poly(oxy-1 ,2-ethanediyl) (TINUVIN® 1130); 2-(2- hydroxy-3,5-di-t-butylphenyl) benzotriazole (TINUVIN® 320); 2-(2-hydroxy-3-t-butyl-5- methylphenyl)-5-chloro-2H-benzotriazole (TINUVIN® 326); 2-(3'-5'-di-t-butyl-2'- hydroxyphenyl-)-5-chlorobenzotriazole (TINUVIN® 327); 2-(2-hydroxy-3,5-di-t- amylphenyl)benzotriazole (TINUVIN® 328); 2-(2H-benzotriazol-2-yl)-4-(1 , 1 ,3,3- tetramethylbutyl)phenol (TINUVIN® 329); 3-(2H-Benzotriazol-2-yl)-5-t-butyl-4- hydroxybenzenepropanoic acid (TINUVIN® 384); 2-(2H-benzotriazol-2-yl)-4-methyl-6- dodecylphenol (TINUVIN® 571 ); 3-(2H-benzotriazol-2-yl)-5-t-butyl-4-hydroxy-1 ,6- hexanediyl ester of benzenepropanoic acid, 3-(2H-benzotriazol-2-yl)-5-t-but-yl-4- hydroxy-methyl ester of benzenepropanoic acid (TINUVIN® 840); 2-[2-hydroxy-3,5- bis-(1 ,1-dimethylbenzyl) phenyl]-2H-benzotriazole (TINUVIN® 900); 2-(2H- benzotriazol-2-yl)-6-(1-methyl-1-phenylethyl)-4-(1 ,1 ,3- ,3-tetramethylbutyl) phenol (TINUVIN® 928); 3-(2H-benzotriazol-2-yl)-5-t-butyl-4-hydroxybenzenepropanoic acid, C7-9 branched and linear alkyl esters (TINUVIN® 99); 2-(2H-benzotriazol-2-yl)-p- cresol (TINUVIN® P); 2-(2'-hydroxy-3'-sec-butyl-5'-t-butylphenyl) benzotriazole (TINUVIN® 350); 2-(2'-hydroxy-5'-t-butylphenyl) benzotriazole (TINUVIN® PS); 2,2'- methylenebis(6-(2H-benzotriazol-2-yl)-4-1 ,1 ,3,3-tetramethylbutyl)phenol (TINUVIN® 360); 2-(2H-benzo[d][1 ,2,3]triazol-2-yl)-4,6-bis(2-phenylpropan-2-yl)phenol (TINUVIN® 234); TINUVIN® B 75; 2,2'-(p-phenylene) di-3,1-benzoxazin-4-one (CYASORB® 3638); dimethyl(p-methoxybenzylidene)malonate (SANDUVOR® PR 25); 3-(4-methoxyphenyl)-2-propenoic acid 2-ethylhexyl ester, octyl p- methoxycinnamate, 3-(4-methylbenzylidene)-D,L-camphor (GIVSORB® UV-15); ethyl-4-[[(methylphenylamino)methylene]amino]benzoate (GIVSORB® UV-2, TINUVIN® 101 ); N-(2-ethoxyphenyl)-N'-(4-isododecylphenyl) oxamide (SANDUVOR 3206); N-[5-t-butyl-2-ethoxyphenyl)-N'-(2-ethylphenyl) oxamide (TINUVIN® 315); N- (2-ethoxyphenyl)-N'-(2-ethylphenyl) oxamide (TINUVIN® 312); 2H-benzimidazole-2- carboxylic acid (4-ethoxyphenyl) amide (UVINUL® FK 4105); 4,4'-dioctyloxyoxanilide, 2,2'-diethoxyoxanilide, 2,2'-dioctyloxy-5,5'-di-tert-butoxanilide, 2,2'-didodecyloxy-5,5'- di-tert-butoxanilide, 2-ethoxy-2'-ethyloxanilide, N,N'-bis(3- dimethylaminopropyl)oxamide, 2-ethoxy-5-tert-butyl-2'-ethoxanilide, bis(2, 2,6,6- tetramethyl-4-piperidyl)sebacate (TINUVIN® 770); N,N1-bis(2I2>6,6-tetramethyl-4- piperidyl)- N,N'-hexamethylenebis(formamide) (UVINUL® 4050H); polymer of 2,2,4,4-tetxamethyl-7-oxa-3,20-diaza-20-(2,3-epoxi-propyl)-dispiro-(5.1.11.2)- heneicosane-21-one (HOSTAVIN® N 30); bis(2,2,6,6-tetramethyl-1-(octyloxy)-4- piperidinyl) decanedioic acid ester (TINUVIN® 123); ester of [(4- methoxyphenyl)methylene]-, bis(1 ,2,2,6,6-pentamethyl-4-piperidinyl)propanedioic acid (SANDUVOR® PR-31 ); copolymer of dimethlylester of 4-hydroxy-2,2,6,6- tetramethyl-1-piperaidine ethanol butanedioic acid (TINUVIN® 622) and bis(2,2,6,6- tetramethyl-4-piperidyl)sebacate (TINUVIN® 783); 1 ,1l,1"-(1 >3,5-tria2ine-2,4I6- triyltris((cyclohexylimino)-2,1-eth- anediyl) tris(3,3,4,5,5- pentamethylpiperazinone (GOODRITE® UV 3159); 1 ,6-Hexanediamine, N, NI-bis(2,2,6,6-tetramethyl-4- piperidinyl)-polymer with 2,4,6-trichloro-1 ,3,5-triazine, reaction products with N-butyl- 1-butanamine an N-butyl-2,2,6,6-tetramethyl-4-piperidinamine (CHIMASSORB® 2020); polymethylpropyl-3-oxy-4(2,2,6,6-tetramethyl)p- iperidinyl)siloxane (UVASIL® 299); bis(2,2,6,6-tetramethyl-4-piperidyl)succinate, bis(1 ,2,2,6,6-pentamethyl-4- piperidyl)sebacate, bis(1 -octyloxy-2,2,6,6-tetramethyl-4-piperidyl)sebacate, poly[[6- [(1 ,1 ,3,3,-tetramethylbutyl)amino]-1 ,3,5-triazine-2,4-diyl][(2,2,6,6-tetranriethyl-4- piperidinyl)imino]-1 )6-hexanediyl[(2,2,6,,6-tetramethyl-4-piperidinyl)imino]]) (CHIMASSORB® 944); bis(1 ,2F2,6,6-pentamethyl-4-piperidyl) n-butyl-3,5-di-tert- butyl-4-hydroxybenzylmalonate; the condensate of 1-(2-hydroxyethyl)-2, 2,6,6- tetramethyl-4-hydroxypiperidine and succinic acid; the condensate of N1N1- bis(2,2,6,6-tetramethyl-4-piperidyl)hexamethylenediamine and 4-tert-octylamino-2,6- dichloro-1 ,3,5-triazine, tris(212>6,6-tetramethyl-4-piperidyl)nitrilotriacetate; tetrakis(2,2,6,6-tetramethyl-4-piperidyl)-1 ,2,3,4-butane-tetracarboxylate, 1 ,1'-(1 ,2- ethanediyl)bis(3,3,5,5-tetramethylpiperazinone), 4-benzoyl-2, 2,6,6- tetramethylpiperidine, 4-stearyloxy-2,2l6,6-tetramethylpiperidine, bis(1 ,2,2,6,6- pentamethylpiperidyl)-2-n-butyl-2-(2-hydroxy-3,5-di-tert-butylbenzyl)malonate, 3-n- octyl-7,7,9,9-tetramethyl-1 ,3,8-triazaspiro[4.5]decan-2,4-dion, bis(1 -octyloxy-2,2,6,6- tetramethylpiperidyl)sebacate, bis(1-octyloxy-2l2,6,6-tetramethylpiperidyl)succinate, the condensate of N,N'-bis-(2,2,6,6-tetramethyl-4-piperidyl)hexamethylenediamine and 4-morpholino-2,6-dichloro-1 ,3,5-triazine; the condensate of 2-chloro-4,6-bis(4-n- butylamino-2,2,6,6-tetramethylpiperidyl)-1 ,3,5-triazine and 1 ,2-bis(3- aminopropylamino)ethane; the condensate of 2-chloro-4,6-di-(4-n-butylamino- 1 , 2, 2,6,6-pentamethylpiperidyl)-1 ,3,5-triazine and 1 ,2-bis-(3- aminopropylamino)ethane; δ-acetyl-S-dodecyl^J.Θ.Θ-tetramethyM .S.δ- triazaspiro[4.5]decane-2,4-dione, 3-dodecyl-1-(2,2,6,6-tetramethyl-4- piperidyl)pyrrolidin-2,5-dione, 3-dodecyl-1 -(1 ,2,2,6, 6-pentamethyl-4- piperidyl)pyrrolidine-2,5-dione, a mixture of 4-hexadecyloxy- and 4-stearyloxy- 2,2,6,6-tetramethylpiperidine; a condensation product of N,N1-bis(2,2,6,6-tetramethyl- 4-piperidyl)hexamethylenediamine and 4-cyclohexylamino-2,6-dichloro-1 ,3,5-triazine; N-(2,2,6,6-tetramethyl-4-piperidyl)-n-dodecylsuccinimid, N-(1 ,2,2,6,6-pentamethyl-4- piperidyl)-n-dodecylsuccinimid, 2-undecyl-7,7,9,9-tetramethyl-1-oxa-3,8-diaza-4-oxo- spiro[4,5]decane, a reaction product of 7,7, θ.θ-tetramethyl^-cycloundecyl-i-oxa-S, 8- diaza-4-oxospiro [4,5]decane and epichlorohydrine, titanium dioxide, zinc oxide, zinc cerium oxide, carbon black, cadmium sulfide, cadmium selenide, chromium oxide, iron oxide, lead oxide, zirconium oxide, bis (1 ,2,2,6,6-pentamethyl-4-piperidinyl)-2- butyl-2-(4-hydroxy-3,5-di-tert.-butylbenzyl)propanedioate (TINUVIN® 144); 4-t-butyl- 4'-methoxydibenzoylmethane, avobenzone (GIVSORB® UV-14); nickel dibutyldithiocarbamate; thio bis2,2'-[4-(1 ,1 ,3,3-tetramethylbutyl)-phenyl- ]nickel-2- ethyl hexanoate; n-butylamine-nickel-2,2'-thio bis(4-t-octylphenolate), nickel-bis-[2,2'- thio bis(4-t-octylphenolate)], octylphenyl salicylate, 4-t-butylphenylsalicylate (SEESORB® 202); S.S.δ-trimetylcyclohexylsalicylate or homomentyylsalicylate (NEO® HELIOPAN HMS); menthyl-o-aminobenzoate (NEO® HELIOPAN MA); 2-[4,6-bis(2,4- dimethylphenyl)-1 ,3,5-triazin-2-yl]-5-octyloxyphenol (CYASORB® UV 1164); confidential triazine derivative (TINUVIN® 1545); 2-(4>6-diphenyl-1 ,3,5-triazin-2-yl)-5- hexyloxyphenol (TINUVIN® 1577 FF); 2-[4-((2-hydroxy-3-dodecyloxypropyl)oxy)-2- hydroxyphenyl]-4,6-bis(2,4-dimethylphenyl)-1 ,3,5-triazine (TINUVIN® 400); 2,4,6- Trianilino-p-(carbo-2'-ethylhexyl-r-oxy)-1 ,3,5-triazine (UVINUL® T-150); 2, 4-bis(2, 4- dihydroxyphenyl)-6-(1-methyl-1 H-pyrazol-5-yl)-1 ,3,5-triazine, 2,4-bis{[4-(2- ethylhexyloxy)-2-hydroxy]phenyl}-6-(1-methyl-1 H-pyrazol-5-yl)-1 ,3,5-triazine, 2-[2, 4- bis (2-ethylhexyloxy)phenyl]-4-[4-(2-ethylhexyloxy)-2-hydroxyphenyl]-6-(1 -methyl-1 H- pyrazol-5-yl)-1 ,3,5-triazine, 2,4-bis(2, 4-dihydroxyphenyl)-6(1-phenyl-1 H-pyrazol-5- yl)-1 ,3,5-triazine, 2,4-bis{[4-(2-ethylhexyloxy)-2-hydroxy]phenyl}-6-(1-phenyl-1 H- pyrazol-5-yl)-1 ,3,5-triazine, 2,4-bis [4-(butoxycarbonyl)phenylamino]-6-(1 -methyl-1 H- pyrazol-5-yl)-1 ,3,5-triazine, 2,4-bis{4-[(2-(ethylhexyloxy)carbonyl]phenylamino}-6-(1 - methyl-1 H-pyrazol-5-yl)-1 ,3,5-triazine, 2,4-bis [4-(butoxycarbonyl)phenylamino]-6-(1- phenyl-1 H-pyrazol-5-yl)-1 ,3,5-triazine, 2,4-bis{4-[(2- ethylhexyloxy)carbonyl]phenylamino}-6-(1-phenyl-1 H-pyrazol-5-yl)-1 ,3,5-triazine, 2- [(4-butoxycarbonyl)phenylamino]-4,6-bis(1 -methyl-1 H-pyrazol-5-yl)-1 ,3,5-triazine, 2- (1-benzyl-1 H-pyrrol-2-yl)-4,6-bis(2,4-dihydroxyphenyl)-1 ,3,5-triazine, 2-(1-benzyl-1 H- pyrrol-2-yl)-4,6-bis[4-(2-ethylhexyloxy)-2-hydroxyphenyl]-1 ,3,5-triazine, 2-(1 -benzyl- 1 H-pyrrol-2-yl)-4,6-bis[4-(butoxycarbonyl)phenylamino]-1 ,3,5-triazine, 2-(1-benzyl- 1 H-pyrrol-2-yl)-4,6-bis(biphenyl-4-ylamino)-1 ,3,5-triazine, 2-(1-benzyl-1 H-pyrrol-2-yl)- 4,6-bis(4-benzoylphenylamino)-1 ,3,5-triazine, 2-(1-benzyl-1 H-pyrrol-2-yl)-4,6-bis(9- oxo-9H-fluoren-3-ylamino)-1 ,3,5-triazine, 2-(1-benzyl-1 H-pyrrol-2-yl)-4,6-bis[4- (imidazo[1 ,2-a]pyridin-2-yl)phenylamino]-1 ,3,5-triazine, 2-(1-benzhydryl-1 H-pyrrol-2- yl)-4,6-bis[4-(butoxycarbonyl)phenylamino]-1 ,3,5-triazine, 2-(1-benzyl-1 H-pyrrol-2-yl)- 4,6-bis[4-(6,6-dimethyl-4-oxo-4,5, 6, 7-tetrahydroindol-1-yl)phenylamino]-1 ,3,5-triazine, 2-(1 -benzyl-1 H-pyrrol-2-yl)-4,6-bis[4-((2-ethylhexyloxy)carbonyl)phenylamino]-1 ,3,5- triazine, 2-(1-benzyl-1 H-pyrrol-2-yl)-4,6-bis[4-1 H-imidazo[1 ,2-a]pyridin-2- yl)phenylamino]-1 ,3,5-triazine, 2-(1 -benzyl-1 H-pyrrol-2-yl)-4,6-bis[4-(1 H- benzo[d]imidazol-2-yl)phenylamino]-1 ,3,5-triazine, 2-(1 -benzyl-1 H-pyrrol-2-yl)-4,6- bis[4-(1 H-pyrazol-1-yl)phenylamino]-1 ,3,5-triazine, 2-(1 -benzyl-1 H-pyrrol-2-yl)-4,6- bis[naphthalen-2-ylamino]-1 ,3,5-triazine, 2-(1 -benzyl-1 H-pyrrol-2-yl)-4,6-bis[4-((E)-3- ethoxy-3-oxoprop-1 -enyl)phenylamino]-1 ,3,5-triazine and 2-(1 -benzyl-1 H-pyrrol-2-yl)- 4,6-bis[4-(E)-styrylphenylamino]-1 ,3,5-triazine, in an amount of 0.01 to 25 % by weight, based on the total weight of the composition.
A further aspect of the present invention relates to a light stabilizer combination comprising at least one heptaazaphenalene compound as defined above and at least one further light stabilizer (Z) of general formulae (L1 ), (L2), (L3), (L4), (L5), (L6), (L7), (L8), (L9), (L10), (L11 ), (L12), (L13) and/or (L14) as defined above;
and optionally at least one further light stabilizer (Z) of general formula (X) and/or (Is) as defined above, preferably in an amount of 0.01 to 25 % by weight, based on the total weight of the composition.
A further aspect of the present invention relates to a light stabilizer combination comprising at least one heptaazaphenalene compound as defined above and at least one further light stabilizer (Z) selected from the group comprising isooctyl α-cyano-β, β-di-phenylacrylate, methyl α-carbomethoxycinnamate, methyl α-cyano-β-methyl-p- methoxycinnamate, butylα-cyano-β-methyl-p-methoxy-cinnamate, methyl α- carbomethoxy-p-methoxycinnamate, N-(β-carbomethoxy-β-cyanovinyl)-2- methylindoline, ethyl-2-cyano-3,3-diphenylacrylate (UVINUL® 3035); 2-ethylhexyl-2- cyano-3,3-diphenylacrylate (UVINUL® 3039); 1 ,3-bis-[(2'-cyano-3,3I- diphenylacryloyl)oxy]-2,2-bis-{[(2-cyano-3',3'-di- phenylacryloyl)oxy]methyl}propane (UVINUL® 3035); 2-cyano-3-(2-methylindolin- yl) methylacrylate (UV Absorber Bayer 340); 2-phenyl-1 H-benzimidazole-5-sulfonic acid (GIVSORB® UV-16); dibenzoyl resorcinol, bis(4-tert-butylbenzoyl) resorcinol, benzoyl resorcinol, 2,4-di- tertbutylphenyl 3,5-di-tert-butyl-4-hydroxybenzoate, hexadecyl 3,5-di-tert-butyl-4- hydroxybenzoate, octadecyl 3,5-di-tert-butyl-4-hydroxybenzoate, 2-methyl-4,6-di-tert- butylphenyl 3,5-di-tert-butyl-4-hydroxybenzoate, hexadecyl 3,5-di-t-butyl-4- hydroxybenzoate (CYASORB® UV 2908); 3-hydroxyphenylbenzoate (SEESORB® 300); ethyl-4-[[(ethylphenylamino)methylene]amino]benzoate (GIVSORB® UV-1 ); phenyl 2-hydroxybenzoate or phenylsalicylate (SEESORB® 201 ); 2,4-di-t- butylphenyl-3,5-di-t-butyl-4-hydroxybenzoate (TINUVIN® 120); 4- bis(polyethoxy)amino acid polyethoxy ethyl ester (UVINUL® P 25); 4-t-butylphenyl 2- hydroxybenzoate, 2-hydroxy-4-octyloxybenzophenone (UVINUL® 3008); 2-hydroxy-4- methoxybenzophenone (UVINUL® 3040); 2-hydroxy-4-methoxy-5- sulfobenzophenone or sulisobenzone (UVINUL® MS 40); 2-(4-Benzoyl-3- hydroxyphenoxy)-2-propenoic acid ethyl ester (CYASORB® UV 2098); homopolymer of 4-(2-acryloyloxyethoxy)-2-hydroxybenzophenone (CYASORB® UV 2126); 2,2'- dihydroxy-4-methoxybenzophenone or dioxybenzone (CYASORB® UV 24); 2- hydroxy-4-(2-hydroxy-3-decyloxypropoxy)benzophenone, 2-hydroxy-4-(2-hydroxy-3- octyloxypropoxy)benzophenone (MARK® 1535); 2,4,4'-trihydroxybenzophenone (MAXGARD® 200); 2-hydroxy-4-(isooctyloxy) benzophenone (MAXGARD® 800); 2- hydroxy-4-dodecyloxybenzophenone (UVINUL® 410); 2,2I-dihydroxy-4,4'-dimethoxy- 5,5'-disulfobenzophenone, disodium salt (UVINUL® 3048); 2,4- dihydroxybenzophenone (UVINUL® 400); 2,2'-dihydroxy-4,4I- dimethoxybenzophenone (UVINUL® D 49); 2,2',4,4'-tetrahydroxybenzophenone (UVINUL® D 50); 2,2'-dihydroxy-4-(2-hydroxyethoxy)benzophenone (UVINUL® X-19); 2-hydroxy-4-benzyloxybenzophenone (SEESORB® 105); 2-hydroxy-4- hydroxybenzophenone, 2-hydroxy-4-decyloxybenzophenone, 2-hydroxy-4,2',4'- trihydroxybenzophenone, 2-hydroxy-4-(octyloxy)benzophenone (CHIMASSORB® 81 ); 2-hydroxy-2'-hydroxy-4,4'-dimethoxybenzophenone, 3,3',4',5J- pentahydroxyflavone, quercetin, 2-(2H-benzotriazol-2-yl)-6-dodecyl-4-methyl-phenol, methyl 3-(3-(2H-benzotriazole-2-yl)-5-t-butyl-4-hydroxyphenyl) propionate/PEG 300 (TINUVIN® 213); 6-tert-butyl-2-(5-chloro-2H-benzotriazole-2-yl)-4-methylphenol (UVINUL® 3026); 6-tert-butyl-2-(5-chloro-2H-benzotriazole-2-yl)-4-methylphenol (UVINUL® 3027); 2,4-di-tert-butyl-6-(5-chloro-2H-benzotriazole-2-yl)-phenol (UVINUL® 3028); 2-(2H-benzotriazole-2-yl)-4-(1 ,1 ,3,3-tetramethylbutyl)-phenol (UVINUL® 3029); 2-(2H-benzotriazole-2-yl)-4-methylphenol (UVINUL® 3033 P); 2- (2H-benzotriazole-2-yl)-4,6-bis(1-methyl-1-phenylethyl)phenol (UVINUL® 3034); 2-(2'- hydroxy-5'-(2-hydroxyethyl))benzotriazole (NORBLOC® 6000); 2-(2'-hydroxy-5'- methacrylyloxyethylphenyl)-2H-benzotriazole (NORBLOC® 7966); 1 ,1 ,1- tris(hydroxyphenyl) ethane benzotriazole (THPE BZT); 5-t-butyl-3-(5-chloro-2H- benzotriazol-2-yl)-4-hydroxybenzenepropanoic acid octyl ester, 3-(5-chloro-2H- benzotriazol-2-yl)-5-t-butyl-4-hydroxybenzenepropanoic acid octyl ester (TINUVIN® 109); a-[3-[3-(2H-benzotriazol-2-yl)-5-t-butyl-4-hydroxyphenyl]-1 -oxopropyl]-w- hydroxypoly(oxy-1 ,2-ethane-diyl), a-[3-[3-(2H-benzotriazol-2-yl)-5-t-butyl-4- hydroxyphenyl]-1-oxopropyl]-w-[3-[3-(2H-benzotriazol-2-yl)-5-t-butyl-4- hydroxyphenyl]-1-oxopropoxy]poly(oxy-1 ,2-ethanediyl) (TINUVIN® 1130); 2-(2- hydroxy-3,5-di-t-butylphenyl) benzotriazole (TINUVIN® 320); 2-(2-hydroxy-3-t-butyl-5- methylphenyl)-5-chloro-2H-benzotriazole (TINUVIN® 326); 2-(3'-51-di-t-butyl-2l- hydroxyphenyl-)-5-chlorobenzotriazole (TINUVIN® 327); 2-(2-hydroxy-3,5-di-t- amylphenyl)benzotriazole (TINUVIN® 328); 2-(2H-benzotriazol-2-yl)-4-(1 , 1 ,3,3- tetramethylbutyl)phenol (TINUVIN® 329); 3-(2H-Benzotriazol-2-yl)-5-t-butyl-4- hydroxybenzenepropanoic acid (TINUVIN® 384); 2-(2H-benzotriazol-2-yl)-4-methyl-6- dodecylphenol (TINUVIN® 571 ); 3-(2H-benzotriazol-2-yl)-5-t-butyl-4-hydroxy-1 ,6- hexanediyl ester of benzenepropanoic acid, 3-(2H-benzotriazol-2-yl)-5-t-but-yl-4- hydroxy-methyl ester of benzenepropanoic acid (TINUVIN® 840); 2-[2-hydroxy-3,5- bis-(1 ,1-dimethylbenzyl) phenyl]-2H-benzotriazole (TINUVIN® 900); 2-(2H- benzotriazol-2-yl)-6-(1-methyl-1-phenylethyl)-4-(1 ,1 ,3- ,3-tetramethylbutyl) phenol (TINUVIN® 928); 3-(2H-benzotriazol-2-yl)-5-t-butyl-4-hydroxybenzenepropanoic acid, C7-9 branched and linear alkyl esters (TINUVIN® 99); 2-(2H-benzotriazol-2-yl)-p- cresol (TINUVIN® P); 2-(2'-hydroxy-3'-sec-butyl-5'-t-butylphenyl) benzotriazole (TINUVIN® 350); 2-(2'-hydroxy-5'-t-butylphenyl) benzotriazole (TINUVIN® PS); 2,2'- methylenebis(6-(2H-benzotriazol-2-yl)-4-1 ,1 ,3,3-tetramethylbutyl)phenol (TINUVIN® 360); 2-(2H-benzo[d][1 ,2,3]triazol-2-yl)-4,6-bis(2-phenylpropan-2-yl)phenol (TINUVIN® 234); TINUVIN® B 75; 2,2'-(p-phenylene) di-3,1-benzoxazin-4-one (CYASORB® 3638); dimethyl(p-methoxybenzylidene)malonate (SANDUVOR® PR 25); 3-(4-methoxyphenyl)-2-propenoic acid 2-ethylhexyl ester, octyl p- methoxycinnamate, 3-(4-methylbenzylidene)-D,L-camphor (GIVSORB® UV-15); ethyl-4-[[(methylphenylamino)methylene]amino]benzoate (GIVSORB® UV-2, TINUVIN® 101 ); N-(2-ethoxyphenyl)-N'-(4-isododecylphenyl) oxamide (SANDUVOR 3206); N-[5-t-butyl-2-ethoxyphenyl)-N'-(2-ethylphenyl) oxamide (TINUVIN® 315); N- (2-ethoxyphenyl)-N'-(2-ethylphenyl) oxamide (TINUVIN® 312); 2H-benzimidazole-2- carboxylic acid (4-ethoxyphenyl) amide (UVINUL® FK 4105); 4,4'-dioctyloxyoxanilide, 2,2'-diethoxyoxanilide, 2,21-dioctyloxy-5,5'-di-tert-butoxanilide, 2,2'-didodecyloxy-5,5'- di-tert-butoxanilide, 2-ethoxy-2'-ethyloxanilide, N,N'-bis(3- dimethylaminopropyl)oxamide, 2-ethoxy-5-tert-butyl-2'-ethoxanilide, bis(2, 2,6,6- tetramethyl-4-piperidyl)sebacate (TINUVIN® 770); N,N'-bis(2,2,6,6-tetramethyl-4- piperidyl)- N,N'-hexamethylenebis(formamide) (UVINUL® 4050H); polymer of 2,2,4,4-tetxamethyl-7-oxa-3,20-diaza-20-(2,3-epoxi-propyl)-dispiro-(5.1.11.2)- heneicosane-21-one (HOSTAVIN® N 30); bis(2,2,6,6-tetramethyl-1-(octyloxy)-4- piperidinyl) decanedioic acid ester (TINUVIN® 123); ester of [(4- methoxyphenyl)methylene]-, bis(1 ,2,2,6,6-pentamethyl-4-piperidinyl)propanedioic acid (SANDUVOR® PR-31 ); copolymer of dimethlylester of 4-hydroxy-2,2,6,6- tetramethyl-1-piperaidine ethanol butanedioic acid (TINUVIN® 622) and bis(2,2,6,6- tetramethyl-4-piperidyl)sebacate (TINUVIN® 783); i
Figure imgf000099_0001
triyltris((cyclohexylimino)-2,1-eth- anediyl) tris(3,3,4,5,5- pentamethylpiperazinone (GOODRITE® UV 3159); 1 ,6-Hexanediamine, N, N'-bis(2,2,6,6-tetramethyl-4- piperidinyl)-polymer with 2,4,6-trichloro-1 ,3,5-triazine, reaction products with N-butyl- 1-butanamine an N-butyl-2,2,6,6-tetramethyl-4-piperidinamine (CHIMASSORB® 2020); polymethylpropyl-3-oxy-4(2,2,6,6-tetramethyl)p- iperidinyl)siloxane (UVASIL® 299); bis(2,2,6,6-tetramethyl-4-piperidyl)succinate, bis(1 , 2,2,6, 6-pentamethyl-4- piperidyl)sebacate, bis(1 -octyloxy-2,2,6,6-tetramethyl-4-piperidyl)sebacate, poly[[6- [(1 ,1 ,3,3,-tetramethylbutyl)amino]-1 ,3,5-triazine-2,4-diyl][(2,2,6)6-tetramethyl-4- piperidinyl)imino]-1 ,6-hexanediyl[(2,2,6,,6-tetramethyl-4-piperidinyl)imino]]) (CHIMASSORB® 944); bis(1 ,2,2,6,6-pentamethyl-4-piperidyl) n-butyl-3,5-di-tert- butyl-4-hydroxybenzylmalonate; the condensate of 1-(2-hydroxyethyl)-2,2,6,6- tetramethyl-4-hydroxypiperidine and succinic acid; the condensate of N1N'- bis(2,2,6,6-tetramethyl-4-piperidyl)hexamethylenediamine and 4-tert-octylamino-2,6- dichloro-1 ,3,5-triazine, tris(2,2,6>6-tetramethyl-4-piperidyl)nitrilotriacetate; tetrakis(2>2,6,6-tetramethyl-4-piperidyl)-1 ,2,3,4-butane-tetracarboxylate, 1 ,1 '-(1 ,2- ethanediyl)bis(3,3,5,5-tetramethylpiperazinone), 4-benzoyl-2, 2,6,6- tetramethylpiperidine, 4-stearyloxy-2,2,6,6-tetramethylpiperidine, bis(1 ,2,2,6,6- pentamethylpiperidyl)-2-n-butyl-2-(2-hydroxy-3,5-di-tert-butylbenzyl)malonate, 3-n- octyl-7,7,9,9-tetramethyl-1 ,3,8-triazaspiro[4.5]decan-2,4-dion, bis(1 -octyloxy-2,2,6,6- tetramethylpiperidyl)sebacate, bis(1-octyloxy-2,2,6,6-tetramethylpiperidyl)succinate, the condensate of N,N'-bis-(2,2,6,6-tetramethyl-4-piperidyl)hexamethylenediamine and 4-morpholino-2,6-dichloro-1 ,3,5-triazine; the condensate of 2-chloro-4,6-bis(4-n- butylamino-2,2,6,6-tetramethylpiperidyl)-1 ,3,5-triazine and 1 ,2-bis(3- aminopropylamino)ethane; the condensate of 2-chloro-4,6-di-(4-n-butylamino- 1 ,2,2,6,6-pentamethylpiperidyl)-1 ,3,5-triazine and 1 ,2-bis-(3- aminopropylamino)ethane; δ-acetyl-S-dodecyl-y.Z.Θ.Θ-tetramethyl-I .S.δ- triazaspiro[4.5]decane-2,4-dione, 3-dodecyl-1-(2,2,6,6-tetramethyl-4- piperidyl)pyrrolidin-2,5-dione, 3-dodecyl-1 -(1 ,2,2,6,6-pentamethyl-4- piperidyl)pyrrolidine-2,5-dione, a mixture of 4-hexadecyloxy- and 4-stearyloxy- 2,2,6, 6-tetramethylpiperidine; a condensation product of N,N'-bis(2,2,6,6-tetramethyl- 4-piperidyl)hexamethylenediamine and 4-cyclohexylamino-2,6-dichloro-1 ,3,5-triazine; N-(2,2,6,6-tetramethyl-4-piperidyl)-n-dodecylsuccinimid, N-(1 ,2,2,6,6-pentamethyl-4- piperidyl)-n-dodecylsuccinimid, 2-undecyl-7,7,9,9-tetramethyl-1-oxa-3,8-diaza-4-oxo- spiro[4,5]decane, a reaction product of 7, T.Θ.Θ-tetramethyl^-cycloundecyM-oxa-S.δ- diaza-4-oxospiro [4,5]decane and epichlorohydrine, titanium dioxide, zinc oxide, zinc cerium oxide, carbon black, cadmium sulfide, cadmium selenide, chromium oxide, iron oxide, lead oxide, zirconium oxide, bis (1 , 2,2,6, 6-pentamethyl-4-piperidinyl)-2- butyl-2-(4-hydroxy-3,5-di-tert.-butylbenzyl)propanedioate (TINUVIN® 144); 4-t-butyl- 4'-methoxydibenzoylmethane, avobenzone (GIVSORB® UV-14); nickel dibutyldithiocarbamate; thio bis2,2'-[4-(1 ,1 ,3,3-tetramethylbutyl)-phenyl- ]nickel-2- ethyl hexanoate; n-butylamine-nickel-2,2'-thio bis(4-t-octylphenolate), nickel-bis-[2,2'- thio bis(4-t-octylphenolate)], octylphenyl salicylate, 4-t-butylphenylsalicylate (SEESORB® 202); SAS-trimetylcyclohexylsalicylate or homomentyylsalicylate (NEO® HELIOPAN HMS); menthyl-o-aminobenzoate (NEO® HELIOPAN MA); 2-[4,6-bis(2,4- dimethylphenyl)-1 ,3,5-triazin-2-yl]-5-octyloxyphenol (CYASORB® UV 1164); confidential triazine derivative (TINUVIN® 1545); 2-(4,6-diphenyl-1 ,3,5-triazin-2-yl)-5- hexyloxyphenol (TINUVIN® 1577 FF); 2-[4-((2-hydroxy-3-dodecyloxypropyl)oxy)-2- hydroxyphenyl]-4,6-bis(2,4-dimethylphenyl)-1 ,3,5-triazine (TINUVIN® 400) and 2,4,6- Trianilino-p-(carbo-2'-ethylhexyl-1'-oxy)-1 ,3,5-triazine (UVINUL® T-150);
and optionally at least one further light stabilizer (Z) selected from the group comprising 2-ethylhexyl 2-cyano-3,3'-diphenylacrylate, ethyl 2-cyano-3,3'-diphenylacrylate, polymer of N-{(2 and 4)[(2-oxoborn-3-ylidene)methyl]benzyl}acryiamide, methyl 4-aminobenzoate, butyl 4-aminobenzoate, 5-methyl-2-(1-methylethyl)-cyclohexyl 2-aminobenzoate, glyceryl aminobenzoate, 2-ethylhexyl-p-dimethylethyl-aminobenzoate, A- aminobenzamide, homomethyl-N-acetyl-anthranilic acid, menthyl antrhanilate, 2-(1 H- benzimidazol-2-yl)-4-methoxyphenol, 2,2'-bis(benzimidazole), monosodium salt of 2- 2'-bis-(1 ,4-phenylene)1 H-benzimidazole-4,6-disulphonic acid, 2- phenylbenzimidazole-5-sulphonic acid, 5,5',6,6'-tetramethyl-2,21-bis(benzimidazole), 5,5'-dimethyl-2,21-bis(benzimidazole), 6-methoxy-2,2'-bis(benzimidazole), 1 ,4- phenylenebis(2-benzimidazolyl), 1 ,2-phenylenebis)benzimidazolyl), 1 ,4- phenylenebis(N-2-ethylhexyl-2-benzimidazolyl), 1 ,4-phenylenebis(N-tri- methylsilylmethyl-2-benzimidazolyl), 2-(1 H-benzimidazol-2-yl)benzothiazole, 2-(1 H- benzimidazol-2-yl)benzoxazole, N,N'-dimethyl-2,2'-bis(benzimidazole), phenylbenzimidazole-5-sulfonic acid (Ensulizole) and its salts , 2-2'-bis-(1 ,4- phenylene)1 H-benzimidazole-4,6-disulphonic acid, 3-methylbutyl A- (dimethylamino)benzoate, 3,3,5-trimethylcyclohexyl 2-hydroxybenzoate (Homosalate), ethyl 4-aminobenzoate, 4,4-((6-(((1 ,1-di- methylethyl)amino)carbonyl)phenyl)amino) 1 ,3,5-triazine-2,4-diyl)diimino)bis-,bis-(2- ethyl-hexyl)ester) benzoic acid, 2,4-dihydroxy-benzophenone (Benzophenone-1 ), 2,2'-dihydroxy-4-methoxy-benzophenone (dioxybenzone, Benzophenone-8), 2,2'- dihydroxy-4,4'-dimethoxy-benzophenone, 2,2',4I41-tetrahydroxy-benzophenoneI 2- hydroxy-4-methoxy-4'-methyl-benzophenone, hydroxymethoxy-benzophenone sulfonic acid, (2-Hydroxy-4-methoxyphenyl)-phenylmethanone (Benzophenone-3), 2- hydroxy-4-methoxy-benzophenone-5-sulfonic acid (Benzophenone-4) and its salts, 4- phenyl-benzophenone, 2-ethylhexyl-4'-phenyl-benzophenone-2-carboxylate, 2- hydroxy-4-n-octoxy-benzophenone, 4-hydroxy-3-carboxy-benzophenone, 4-(2-β- glucopyranosiloxy)-propoxy-2-hydroxybenzophenone, dihydroxy-dimethoxy-di- sulfobenzophenone, 2-benzothiazol-2-ylphenol, [2,4'-dihydroxy-3-(2H-benzotriazol-2- yl)-5-(1 ,1.S.S-tetramethylbutyO^'-n-octoxy-δ'-benzoyπ-diphenylmethane, 2,2'- hydroxy-5-methylphenyl-benzotriazole, 2-(2'-hydroxy-5'-t-octylphenyl)benzotriazole, 2-(2I-hydroxy-5'-methylphenyl)benzotriazole, 2,2'-methylene-bis-6-(2H-benzotriazol- 2-yl)-4-(tetramethyl-butyl)-1 ,1 ,3,3-phenol, 2-benzoxazole-2-yl-4-methylphenol, 2- phenyl-5-methylbenzoxazole, 1 ,4-phenylenebis(2-benzoxazolyl), 1 ,3-phenylenebis(2- benzoxazolyl), 1 ,2-phenylenebis(2-benzoxazolyl), 2-(2-benzofuryl)-benzoxazole, 2- (benzofuryl)-5-methylbenzoxazole, 2-(3-methyl-2-benzofuryl)benzoxazole, 3-(4'- methylbenzylidene)-D,L-camphor, terephthalylidene dicamphor sulphonic acid, 3- benzylidene-D.L-camphor, 4-benzylidene-D,L-camphor, di-tert-butyl hydroxybenzylidene camphor, benzylidene camphor sulphonic acid, camphor benzalkonium methosulfate, polyacrylamido-methyl benzylidene camphor, ethylhexyl methoxycinnamate, diethanolamine p-methoxy cinnamate, isopropyl-p-acetamido cinnamate, octyl cinnamate, ethyl-4-isopropylcinnamate, methyl-2,5-diisopropyl cinnamate, ethyl-2,4-diisopropylcinnamate, methyl-2,4-diisopropylcinnamate, propyl- p-methoxycinnamate, isopropyl-p-methoxycinnamate, diisopropylcinnamate esters, isoamyl-p-methoxycinnamate, cyclohexyl-p-methoxycinnamate, ethyl-α-cyano-β- phenylcinnamate, 2-ethylhexyl-α-cyano-β-phenylcinnamate, glycerin-mono-2-ethyl- hexanoyl-diparamethoxycinnamate, glyceryl octanoate-di-p-methoxycinnamate, DEA- methoxycinnamate, methyl-bis(trimethyl-siloxy)silyl-isopentyl-trimethoxycinnamate, ethyl-α-cyano-3,5-dimethoxy-4-hydroxy cinnamate, ethyl-α-acetyl-3,5-dimethoxy-4- hydroxy cinnamate, iso-propyl-α-acetyl-3,5-dimethoxy-4-hydroxy cinnamate, iso- amyl-α-acetyl-3,5-dimethoxy-4-hydroxy cinnamate, 2-ethylhexyl-α-acetyl-3,5- dimethoxy-4-hydroxy cinnamate, ethyl-α-cyano-3-methoxy-4-hydroxy cinnamate, ethyl-α-acetyl-3-methoxy-4-hydroxy cinnamate, iso-propyl-α-acetyl-3-methoxy-4- hydroxy cinnamate, iso-amyl-α-acetyl-S-methoxy-^hydroxy cinnamate, 2-ethylhexyl- α-acetyl-3-methoxy-4-hydroxy cinnamate, 7-ethylamino-4-methylcoumarin, 7,8- dihydroxycoumarin, 6,7-dihydroxycoumarin, 7-hydroxycoumarin, 4-methyl-7- hydroxycoumarin, diacetycurcumin, tetrahydrocurcumin diacetate, dianisoylmethane, dibenzalazine, butyl methoxydibenzoylmethane (Avobenzone), 2- methyldibenzoylmethane, 4-methyldibenzoylmethane, 4-isopropyldibenzoylmethane, 4-tert-butyldibenzoylmethane, 2,4-dimethyldibenzoylmethane, 2,5- dimethyldibenzoylmethane, 4,4'-diisopropyldibenzoylmethane, 4,4'- dimethoxydibenzoylmethane, 2-methyl-5-isopropyl-4I-methoxydibenzoylmethane, 2- methyl-5-tert-butyl-4'-methoxydibenzoylmethane, 2,4-dimethyl-4'- methoxydibenzoylmethane, 2,6-dimethyl-4-tert-butyl-41-methoxydibenzoylmethane, ferulic acid, dimethicodiethylbenzalmalonate, diethyl-3,5-dimethoxy-4-hydroxy benzylidene malonate, di-(2-ethylhexyl)-3,5-dimethoxy-4-hydroxy benzylidene malonate, diisoamyl-3,5-dimethoxy-4-hydroxy benzylidene malonate, didodecyl-3,5- dimethoxy-4 hydroxy benzylidene malonate, dipalmitoyl-3,5-dimethoxy-4-hydroxy benzylidene malonate, di-isopropyl-3,5-dimethoxy-4-hydroxy benzylidene malonate, diethyl-3-methoxy-4-hydroxy benzylidene malonate, di-(2-ethylhexyl)-3-methoxy-4- hydroxy benzylidene malonate, diisoamyl-3-methoxy-4-hydroxy benzylidene malonate, didodecyl-3-methoxy-4-hydroxy benzylidene malonate, dipalmitoyl-3- methoxy-4-hydroxy benzylidene malonate, di-isopropyl-3-methoxy-4-hydroxy benzylidene malonate, hydrolyzed aspergillus sp. extract ferment, 4-nitrobenzamide, 4-nitrobenzoic acid, p-aminobenzoic acid (PABA), PABA-monoglycerinester, N1N- dipropoxy-PABA-ethylester, N,N-diethoxy PABA-ethylester, N,N-dimethyl PABA- ethylester, N,N-dimethyl PABA-butylester, PEG-25 PABA, N,N-dimethyl PABA- amylester, N,N-dimethyl PABA-octlylester (2-ethylhexyl 4-(dimethylamino)benzoate, Padimate O)1 octyl dimethyl PABA, ethyl-dihydroxypropyl-PABA, isoamyl dimethyl PABA (3-methylbutyl 4-(dimethylamino)benzoate, Padimate A), 1-(3,4- dimethoxyphenyl)-4,4-diemthyl-1 ,3-pentanedione, 5-(3,3-Dimethyl-2-norbornyliden)- 3-pentane-2-one, 1 -(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1 ,3-dione, dipropylene glycol salicylate, 2-ethylhexyl 2-cyano-3,3-diphenyl-2-propenoate (Octocrylene), hydrolyzed soy extract, hydrolyzed linseed extract, sunflower seed extract, grape seed extract, pinus pinaster bark extract, pinus pinaster bud extract, ginseng extract ferment, spirulina platensis powder, p-tert-butylphenyl salicylate, p- octylphenyl salicylate, 2-ethylhexyl salicylate (octyl salicylate), amyl salicylate, menthyl salicylate, homomenthyl salicylate, benzyl salicylate, p-isopropanol-phenyl salicylate, TEA-salicylate, 2-(2H-benzotriazol-2-yl)-4-methyl-6-[2-methyl-3-[1 ,3,3,3- tetramethyl-1-[(trimethylsilyl)oxy]disiloxanyl]propyl]-phenol (Mexoryl XL), 2-[p-(tert- butylamido)anilino]-4,6-bis[p-(2'-ethylhexyl-1 '-oxycarbonyl)anilino]-1 ,3,5-triazine (INCI name: Diethylhexyl Butamido Triazone), 2,4,6-tris[4-(2-ethylhexyl-oxycarbonyl)- anilino]-1 ,3,5-triazine (INCI name: Ethylhexyl Triazone), (1 ,3,5)-triazine-2,4-bis((4-2- ethyl-hexyloxy)-2-hydroxy)-phenyl)-6-(4-methoxy-phenyl) (bemotrizinol), octyl triazone (CAS-no.: 88122-99-0), 2, 4-bis(2, 4-dihydroxyphenyl)-6-(1-methyl-1H- pyrazol-5-yl)-1 ,3,5-triazine, urocanic acid, ethyl-urocanic acid, talc, kaolin, calcium carbonate, bisoctrizole (CAS-no.: 103597-45-1), bornelone (CAS-no.: 2226-11-1 ), 2- hydroxy-1 ,4-naphthochinone (Lawsone, CAS-no.: 83-72-7), petrolatum red, phenol sulphonate, sodium 3,4-dimethylphenyl-glyoxylate, 3,3'-(1 ,4-phenylenedimethylene- bis-(7,7-dimethyl-2-oxobicyclo-[2,2,1]hept-1-yl-methanesufonic acid, α-(2-oxoborn-3- ylidene)-toluene-4-sulphonic acid, 2-(2H-benzotriazole-2-yl)-4-methyl-6-[2-methyl-3- [1 ,3,3,3-tetramethyl-1-[(trimethylsilyl)oxy]disiloxanyl]propyl]-phenol (INCI name: drometrizole trisiloxane, DTS), digalloyl trioleate, dimethicone/PEG-15 crosspolymer, ethylhexyl-bis-isopentyl-benzoxazolyl-phenyl melamine and 2-ethylhexyl-dimethoxy- benzylidene-dioxo-imidazolidine propionate.
Preferably, this light stabilizer combination is used in an amount of 0.01 to 25 % by weight, based on the total weight of a light-stabilized composition.
Examples
The present invention is further illustrated by means of the following example.
Abbreviations:
MFI melt flow index
PP polypropylene
HEP1 heptaazaphenalene light stabilizer 2,5,8-tris-(4-
(butoxycarbonyl)phenylamino)-1 ,3,4,6,7,9, 9b-heptaazaphenalene (melting point: 289-2900C) HEP2 heptaazaphenalene light stabilizer 2,5,8-tris-(biphenyl-4-ylamino)-
1 , 3,4,6, 7,9,9b-heptaazaphenalene (melting point: >310°C) HEP3 heptaazaphenalene light stabilizer 2,5,8-tris-((4-(£)-styrylphenyl)amino)-
1 ,3,4,6,7,9,9b-heptaazaphenalene (melting point: >270°C, λmax: 367 nm)
Example 1
Master batches of polypropylene (MFI=0.7 g/10 min at 2300C and 2.16 kg) and light- stabilized component set forth in table 1 are prepared by dry blending the polypropylene granulate with the components set forth in table 1 and the mixtures are further processed under melting in a Brabender kneader at 2000C during 10 minutes and at a rotation speed of 75 rounds/min and under a nitrogen atmosphere.
Table 1
Figure imgf000105_0001
Figure imgf000106_0001
piperidinyl)imino]-1 ,6-hexanediyl[(2,2,6,,6-tetramethyl-4-piperidinyl)imino]]);
2 bis(2,2,6,6-tetramethyl-4-piperidyl)sebacate;
3 N,N'-bis(2,2,6,6-tetramethyl-4-piperidyl)- N,N'-hexamethylenebis(formamide) 4 2-(2H-benzotriazol-2-yl)-p-cresol
5 polymer of 2,2,4,4-tetxamethyl-7-oxa-3,20-diaza-20-(2,3-epoxi-propyl)-dispiro-(5.1.11.2)- heneicosane-21-one
6 copolymer of dimethlylester of 4-hydroxy-2,2,6,6-tetramethyl-1-piperaidine ethanol butanedioic acid
(TINUVIN® 622) and bis(2,2,6,6-tetramethyl-4-piperidyl)sebacate;
7 polymethylpropyl-3-oxy-4(2,2,6,6-tetramethyl)p- iperidinyl)siloxane
8 ester of [(4-methoxyphenyl)methylene]-, bis(1 ,2,2,6,6-pentamethyl-4-piperidinyl)propanedioic acid
9 1 ,6-Hexanediamine, N, N'-bis(2,2,6,6-tetramethyl-4-piperidinyl)-polyrner with 2,4,6-trichloro-1 ,3,5- triazine, reaction products with N-butyl-1-butanamine an N-butyl-2,2,6,6-tetramethyl-4- piperidinamine
10 bis(2,2,6,6-tetramethyl-1-(octyloxy)-4-piperidinyl) decanedioic acid ester
11 2-hydroxy-4-(octyloxy)benzophenone
122 22,,22''--mmeetthhyylleenebis(6-(2H-benzotriazol-2-yl)-4-1.1 ,3,3-tetramethylbutyl)phenol % by weight
Each masterbatch is mixed in such an amount with polypropylene (MFI=O.7 g/10 min at 230°C and 2.16 kg) to achieve a light-stabilized PP composition containing 0.15% by weight, based on the total weight of the composition, of the light-stabilizing component and with 0 1 % by weight calcium stearate and 0.05% by weight of a phenolic antioxidant (Irganox 1010) in an extruder equipped with a double screw. Each composition is extruded through a flat nozzle to obtain a film with a thickness adjusted to the requirements of the accelerated weathering test according to ASTM D-5208. Examples of each film are exposed to such wheathering test. The light stability of the sample is assessed by measuring the extent of carbonyl oxidation of the polymer by means of infrared spectroscopy. The measurement is carried out after 1000 hours exposition to accelerated weathering (UV-A).

Claims

1. A light-stabilized composition comprising at least one polymer and 0.01 to 25% by weight, based on the total weight of the composition, of a light-stabilizing component comprising at least one heptaazaphenalene compound of general formula (I),
Figure imgf000107_0001
wherein
R1, F?2 and R3, independent of each other, each represents an unsubstituted or at least mono-substituted mono- or polycyclic aryl radical; an unsubstituted or at least mono-substituted, saturated, unsaturated or aromatic heterocyclic radical having from 5 to 10 atoms that can contain 1 , 2 or 3 heteroatoms independently selected from O, N and S; an -OR4 radical; or a -NRδRβ radical;
R4 represents a hydrogen atom; an unsubstituted or at least mono-substituted, saturated or unsaturated, linear or branched CM8 aliphatic radical; an unsubstituted or at least mono-substituted C3--I2 cycloalkyl radical; an unsubstituted or at least mono-substituted mono- or polycyclic aryl radical; an unsubstituted or at least mono-substituted, saturated, unsaturated or aromatic heterocyclic radical having from 5 to 14 atoms that can contain 1 , 2 or 3 heteroatoms independently selected from O, N and S; R5 and R6, independent of each other, each represents a hydrogen atom; an unsubstituted or at least mono-substituted, saturated or unsaturated, linear or branched Ci-18 aliphatic radical; an unsubstituted or at least mono- substituted C-3-12 cycloalkyl radical; an unsubstituted or at least mono- substituted mono- or polycyclic aryl radical; an unsubstituted or at least mono-substituted, saturated, unsaturated or aromatic heterocyclic radical having from 5 to 10 atoms that can contain 1 , 2 or 3 heteroatoms independently selected from O, N and S;
or
R5 and Re form together with the bridging nitrogen atom an unsubstituted or at least mono-substituted saturated, unsaturated or aromatic mono- or polycyclic ring system having from 4 to 10 atoms that contains optionally 1 or 2 heteroatoms independently selected from N, O and S;
with the proviso that if each radical Ri, R2 and R3 represent a -NR5R6 radical at the same time, and R5 and R6, are identical, then each of the radicals R5 and R6 shall not represent a hydrogen atom;
and/or at least one of its stereoisomers, preferably enantiomers or diastereomers, a racemate or a mixture of at least two of its stereoisomers, preferably enantiomers and/or diastereomers in any mixing ratio, or at least one physiologically acceptable salt thereof, or at least one corresponding solvate thereof;
with the exception of a composition comprising 3% by weight of 2,5,8-tris-(4- (butoxycarbonyl)phenylamino)-1 ,3,4,6,7,9, 9b-heptaazaphenalene
Figure imgf000109_0001
5% by weight of ethylhexyl methoxycinnamate and 16% by weight of Arlamol HD ((Uniqema): Cyclomethicone, PPG-15, stearyl ether), based on the total weight of the composition, respectively;
with the exception of a composition comprising 6% by weight of 2-(4- (carboxy)phenylamino)-5,8-bis-(4-methylphenyl)-1 ,3, 4,6,7,9,9b- heptaazaphenalene
Figure imgf000109_0002
2% by weight of PEG-100 Stearate (Simulsol M59 (Seppic)), 7.5% by weight of Propyleneglycol, Dicaprylate/dicaprate (Estol 1526 PDCC), 0.5% Dimethicone (SF 18-350 (General Electric)), 4% by weight of MT-T100 TV (Tayca: Titanium dioxide, aluminium hydroxide, stearic acid), 0.15% by weight of PNC 30 (sodium acrylates/cross-linked polymer, vinyl isodecanoate) and 1.5% by weight of butyleneglycol, based on the total weight of the composition, respectively;
and
with the exception of a composition comprising 6% by weight of 2,5,8-tris-(4-(2- ethylhexyloxycarbonyl)phenylamino)-1 ,3, 4,6,7,9,9b-heptaazaphenalene
Figure imgf000110_0001
2% by weight of PEG-100 Stearate (Simulsol M59 (Seppic)), 7.5% by weight of Propyleneglycol, Dicaprylate/dicaprate (Estol 1526 PDCC), 0.5% Dimethicone (SF 18-350 (General Electric)), 4% by weight of MT-T100 TV (Tayca: Titanium dioxide, aluminium hydroxide, stearic acid), 0.15% by weight of PNC 30 (sodium acrylates/cross-linked polymer, vinyl isodecanoate) and 1.5% by weight of butyleneglycol, based on the total weight of the composition, respectively.
2. A light-stabilized composition according to claim 1 , characterized in that the light-stabilizing component is at least one heptaazaphenalene compound of general formulae (IA) to (IL)
Figure imgf000110_0002
Figure imgf000111_0001
Figure imgf000111_0002
IL
wherein
R'I , R'2 and R'3, independent of each other, each represents an unsubstituted or at least mono-substituted, mono- or polycyclic aryl radical; an unsubstituted or at least mono-substituted, saturated, unsaturated or aromatic heterocyclic radical having from 5 to 10 atoms that can contain 1 , 2 or 3 heteroatoms independently selected from O, N and S;
R4, R'4l R"4 and R"'4, independent of each other, each represents a hydrogen atom, an unsubstituted or at least mono-substituted, saturated or unsaturated linear or branched Ci-Ie aliphatic radical; an unsubstituted or at least mono-substituted 03-12 cycloalkyl radical; an unsubstituted or at least mono-substituted mono- or polycyclic aryl radical; an unsubstituted or at least mono-substituted saturated, unsaturated or aromatic heterocyclic radical having from 5 to 14 atoms that can contain 1 , 2 or 3 heteroatoms independently selected from O, N and S;
R'δ, R"5, Rm 5, R'β> R' Θ and R"^, independent of each other, each represents a hydrogen atom; an unsubstituted or at least mono-substituted, saturated or unsaturated, linear or branched Ci-i8 aliphatic radical; an unsubstituted or at least mono-substituted C3-^ cycloalkyl radical; an unsubstituted or at least mono-substituted mono- or polycyclic aryl radical; an unsubstituted or at least mono-substituted saturated, unsaturated or aromatic heterocyclic radical having from 5 to 10 atoms that can contain 1 , 2 or 3 heteroatoms independently selected from O, N and S;
or
R's, R"5. Rm 5, R'β. R"β and R'"6, form together with the bridging nitrogen atom an unsubstituted or at least mono-substituted, saturated, unsaturated or aromatic mono- or polycyclic ring system which has 5 to 10 atoms as ring members and which contains optionally 1 , 2 or 3 heteroatoms independently selected from O, N and S;
and/or at least one of its stereoisomers, preferably enantiomers or diastereomers, a racemate or a mixture of at least two of its stereoisomers, preferably enantiomers and/or diastereomers in any mixing ratio, or at least one physiologically acceptable salt thereof, or at least one corresponding solvate thereof.
3. A light-stabilized composition according to claim 1 or 2, characterized in that the light-stabilizing component is at least one heptaazaphenalene compound of general formula (IA)
Figure imgf000112_0001
(IA)
wherein R'4, R"4 and R'"4, independent of each other, each represents an unsubstituted or at least mono-substituted, C3-^ cycloalkyl radical; an unsubstituted or at least mono-substituted mono- or polycyclic aryl radical; an unsubstituted or at least mono-substituted saturated, unsaturated or aromatic heterocyclic radical having from 5 to 14 atoms that can contain 1 , 2 or 3 heteroatoms independently selected from O, N and S;
and/or at least one of its stereoisomers, preferably enantiomers or diastereomers, a racemate or a mixture of at least two of its stereoisomers, preferably enantiomers and/or diastereomers in any mixing ratio, or at least one physiologically acceptable salt thereof, or at least one corresponding solvate thereof.
4. A light-stabilized composition according to claim 1 or 2, characterized in that the light-stabilizing component is at least one heptaazaphenalene compound of general formula (IB)
Figure imgf000113_0001
(IB)
wherein
the radicals within each radical pair R'5 R'β, R"s FTe, and R"'5R'"6, different from each other, each represents a hydrogen atom; an unsubstituted or at least mono-substituted, linear or branched Ci-Is alkyl radical; an unsubstituted or at least mono-substituted C3-I2 cycloalkyl radical; an unsubstituted or at least mono-substituted mono- or polycyclic aryl radical; an unsubstituted or at least mono-substituted, saturated, unsaturated or aromatic heterocyclic radical having from 5 to 10 atoms that can contain 1 , 2 or 3 heteroatoms independently selected from O, N and S;
or
the radical pairs R'5 R'6, R"s R"6> or R'^R"^ form together with the bridging nitrogen atom an unsubstituted or at least mono-substituted, saturated, unsaturated or aromatic mono- or polycyclic ring system having from 4 to 10 atoms as ring members that contains optionally 1 or 2 heteroatoms selected from N, O and S;
preferably with the proviso that if one of the radicals of each radical pair R'5 R'6, R"5 R"6, and R111 SR"^ is hydrogen, the other radical is different from n-butyl, phenyl, hydroxymethyl, 4-methoxy-9,10-dihydro-9,10-dioxoanthracene-1-yl, 9,10-dihydro-9,10-dioxoanthracene-1-yl, 9,10-dihydro-9,10-dioxoanthracene-2- yl, or 5-benzoylamino-9,10-dihydro-9,10-dioxoanthracene-1-yl;
and
and/or at least one of its stereoisomers, preferably enantiomers or diastereomers, a racemate or a mixture of at least two of its stereoisomers, preferably enantiomers and/or diastereomers in any mixing ratio, or at least one physiologically acceptable salt thereof, or at least one corresponding solvate thereof.
5. A light-stabilized composition according to claim 1 or 2, characterized in that the light-stabilizing component is at least one heptaazaphenalene compound of general formula (IC)
Figure imgf000115_0001
(IC)
wherein
R'i, R'2 and R'3, identical or different, each represents an unsubstituted or at least mono-substituted mono- or polycyclic aryl radical; an unsubstituted or at least mono-substituted saturated, unsaturated or aromatic heterocyclic radical having from 5 to 10 atoms that can contain 1 , 2 or 3 heteroatoms independently selected from O, N and S;
and/or at least one of its stereoisomers, preferably enantiomers or diastereomers, a racemate or a mixture of at least two of its stereoisomers, preferably enantiomers and/or diastereomers in any mixing ratio, or at least one physiologically acceptable salt thereof, or at least one corresponding solvate thereof.
6. A light-stabilized composition according to claim 5, characterized in that the light-stabilizing component is at least one heptaazaphenalene compound of general formula (YA)
Figure imgf000116_0001
wherein
R22, R23> R24, R25. R26, R27, R28, R29> R30 and R31 have the following meaning:
Figure imgf000116_0002
Figure imgf000117_0001
Figure imgf000118_0001
Figure imgf000119_0001
Figure imgf000120_0001
-Ph stands for a phenyl radical, -O-But** stand for an -O-butyl radical and -0-Ac*** stand for an 0-acyl radical;
and/or at least one of its stereoisomers, preferably enantiomers or diastereomers, a racemate or a mixture of at least two of its stereoisomers, preferably enantiomers and/or diastereomers in any mixing ratio, or at least one physiologically acceptable salt thereof, or at least one corresponding solvate thereof.
7. A light-stabilized composition according to claims 1 or 2, characterized in that the light-stabilizing component is at least one heptaazaphenalene compound of general formula (YB)
Figure imgf000121_0001
(YB), wherein
R32 represents a radical selected from the group consisting of
Figure imgf000121_0002
and/or at least one of its stereoisomers, preferably enantiomers or diastereomers, a racemate or a mixture of at least two of its stereoisomers, preferably enantiomers and/or diastereomers in any mixing ratio, or at least one physiologically acceptable salt thereof, or at least one corresponding solvate thereof.
8. A light-stabilized composition according to claims 1 or 2, characterized in that the light-stabilizing component is at least one heptaazaphenalene compound of general formula (YC)
Figure imgf000122_0001
wherein R33, R34 and R35 have the following meaning:
Figure imgf000122_0002
and/or at least one of its stereoisomers, preferably enantiomers or diastereomers, a racemate or a mixture of at least two of its stereoisomers, preferably enantiomers and/or diastereomers in any mixing ratio, or at least one physiologically acceptable salt thereof, or at least one corresponding solvate thereof.
9. A light-stabilized composition according to claims 1 or 2, characterized in that the light-stabilizing component is at least one heptaazaphenalene compound of general formula (YD)
Figure imgf000123_0001
(YD), wherein
R36 and R37 have the following meaning:
Figure imgf000123_0002
and/or at least one of its stereoisomers, preferably enantiomers or diastereomers, a racemate or a mixture of at least two of its stereoisomers, preferably enantiomers and/or diastereomers in any mixing ratio, or at least one physiologically acceptable salt thereof, or at least one corresponding solvate thereof.
10. A light-stabilized composition according to claims 1 or 2, characterized in that the light-stabilizing component is a heptaazaphenalene compound of formula (YE)
Figure imgf000124_0001
(YE),
and/or at least one of its stereoisomers, preferably enantiomers or diastereomers, a racemate or a mixture of at least two of its stereoisomers, preferably enantiomers and/or diastereomers in any mixing ratio, or at least one physiologically acceptable salt thereof, or at least one corresponding solvate thereof.
11. A light-stabilized composition according to claim 5, characterized in that the light-stabilizing component is at least one heptaazaphenalene compound of general formula (YF)
Figure imgf000124_0002
(YF), wherein
R38, R39, R40, R41, R42 and R43 have the following meaning:
Figure imgf000125_0001
-Ph stands for a phenyl radical, -CH2-Ph stand for a -CH2-phenyl radical;
and/or at least one of its stereoisomers, preferably enantiomers or diastereomers, a racemate or a mixture of at least two of its stereoisomers, preferably enantiomers and/or diastereomers in any mixing ratio, or at least one physiologically acceptable salt thereof, or at least one corresponding solvate thereof.
12. A light-stabilized composition according to claims 1 or 2, characterized in that the light-stabilizing component is at least one heptaazaphenalene compound of general formula (YG)
Figure imgf000125_0002
(YG),
wherein R44, R45 and R46 have the following meaning:
Figure imgf000126_0001
Figure imgf000127_0001
-Ph stand for a phenyl radical and -C-O-Ph stands for a -C-0-phenyl radical;
and/or at least one of its stereoisomers, preferably enantiomers or diastereomers, a racemate or a mixture of at least two of its stereoisomers, preferably enantiomers and/or diastereomers in any mixing ratio, or at least one physiologically acceptable salt thereof, or at least one corresponding solvate thereof.
13. A light-stabilized composition according to at least one of the preceding claims 1 to 12, characterized in that the light-stabilizing component is at least one heptaazaphenalene compound selected from the group comprising
• 2,5,8-tris-(4-(butoxycarbonyl)phenylamino)-1 ,3,4,6,7,9, 9b- heptaazaphenalene,
• 2,5,8-tris-(4-(2-ethylhexyloxycarbonyl)phenylamino)-1 ,3, 4,6,7,9,9b- heptaazaphenalene,
• 2,5,8-tris-(4-(imidazo[1 ,2-a]pyridin-2-yl)-phenylamino) -1 ,3,4,6,7,9,9b- heptaazaphenalene,
• 2,5,8-tris-(4-(4>5,6,7-tetrahydro-2,6,6-trimethyl-4-oxo indol-1-yl)phenylamine)- 1 ,3,4,6,7,9,9b-heptaazaphenalene,
• 2,5,8-tris-(biphenyl-4-ylamino)-1 ,3,4,6,7,9,9b-heptaazaphenalene,
• 2,5,8-tris-(4-(1 H-benzo[d]imidazol-2-yl)phenylamino)-1 , 3,4,6,7,9,9b- heptaazaphenalene,
• 2,5-bis-(biphenyl-4-ylamino)-8-(4-(butoxycarbonyl)phe nylamino)- 1 , 3,4,6, 7,9,9b-heptaazaphenalene,
• 2-(biphenyl-4-ylamino)-5-(4-(butoxycarbonyl)phenylami no)-8-(4-(2- ethylhexyloxycarbonyl)phenylamino)-1 ,3,4, 6,7,9,9b-heptaazaphenalene, • 2,5,8-tris-(2,4-dihydroxyphenyl)-1.SAΘJ.Θ.Θb-heptaaza phenalene,
• 2,5-dichloro-8-(1 -methyl-1 H-pyrrol-2-yl)-1 ,3,4,6, 7,9, 9b-heptaazaphenalene,
• 2, 5-bis-(4-(butoxycarbonyl)phenylamino)-8-(2-(1 -methyl-1 H-pyrrol-2-yl)- 1 ,3,4,6, 7, 9,9b-heptaazaphenalene,
• 2-(4-(carboxy)phenylamino)-5,8-bis-(4-methylphenyl)-1 ,3, 4,6,7,9,9b- heptaazaphenalene,
• 2I5,8-tris-(4-(4,5,6,7-tetrahydro-2,6,6-trimethyl-4-oxo indol-1 -yl)phenylamine)- 1 ,3,4,6,7,9,9b-heptaazaphenalene,
• 2,5-bis-(4-(butoxycarbonyl)phenylamino)-8-(1 -methyl-1 H-pyrrol-2-yl)- 1 , 3,4,6, 7,9,9b-heptaazaphenalene,
• 2,5-bis(2,4-dihydroxyphenyl)-8-(1 -methyl-1 H-pyrazol-5-yl)-1 ,3,4,6,7,9,9b- heptaazaphenalene,
• 2, 5-bis{[4-(2-ethylhexyloxy)-2-hydroxy]phenyl}-6-(1 -methyl-1 H-pyrazol-5-yl)- 1 , 3,4,6, 7,9,9b-heptaazaphenalene,
• 2-[2,4-bis(2-ethylhexyloxy)phenyl]-5-[4-(2-ethylhexyl oxy)-2-hydroxyphenyl]-8- (1 -methyl-1 H-pyrazol-5-yl)-1 ,3, 4,6,7,9,9b-heptaazaphenalene,
• 2,5-bis(2,4-dihydroxyphenyl)-8-(1 -phenyl-1 H-pyrazol-5-yl)-1 ,3,4,6,7,9,9b- heptaazaphenalene,
• 2, 5-bis{[4-(2-ethylhexyloxy)-2-hydroxy]phenyl}-8-(1 -phenyl-1 H-pyrazol-5-yl)- 1 ,3,4,6,7,9,9b-heptaazaphenalene,
• 2, 5-bis[4-(butoxycarbonyl)phenylamino]-8-(1 -methyl-1 H-pyrazol-5-yl)- 1 ,3,4,6, 7,9, 9b-heptaazaphenalene,
• 2,5-bis{4-[(2-(ethylhexyloxy)carbonyl]phenylamino}-8-(1 -methyl-1 H-pyrazol-5- yl)-1 ,3,4,6,7,9,9b-heptaazaphenalene,
• 2,5-bis[4-(butoxycarbonyl)phenylamino]-8-(1 -phenyl-1 H-pyrazol-5-yl)- 1 ,3,4,6, 7, 9,9b-heptaazaphenalene,
• 2, 5-bis{4-[(2-ethylhexyloxy)carbonyl]phenylamino}-8-(1 -phenyl-1 H-pyrazol-5- yl)-1 , 3,4,6, 7,9,9b-heptaazaphenalene,
• 2-(1 -benzyl-1 H-pyrrol-2-yl)-5,8-bis(2,4-dihydroxy phenyl)-1 ,3,4,6,7,9,9b- heptaazaphenalene,
• 2-(1 -benzyl-1 H-pyrrol-2-yl)-5,8-bis[4-(2-ethylhexyloxy)-2-hydroxyphenyl]- 1 ,3,4,6,7,9,9b-heptaazaphenalene,
• 2-(1 -benzyl-1 H-pyrrol-2-yl)-5,8-bis[4-(butoxycarbonyl) phenylamino]- 1 ,3,4,6, 7, 9,9b-heptaazaphenalene,
• 2-(1 -benzyl-1 H-pyrrol-2-yl)-5,8-bis(biphenyl-4-ylamino)-1 ,3,4,6,7,9,9b- heptaazaphenalene,
• 2-(1 -benzyl-1 H-pyrrol-2-yl)-5,8-bis(4-benzoylphenylami-no)-1 ,3,4,6,7,9,9b- heptaazaphenalene,
• 2-(1 -benzyl-1 H-pyrrol-2-yl)-5,8-bis(9-oxo-9H-fluoren-3-ylamino)-1 ,3,4,6,7,9,9b- heptaazaphenalene,
• 2-(4-(tert-butylcarbamoyl)phenylamino)-5,8-bis-(4-(2- ethylhexyloxycarbonyl)phenylamino)-1 , 3,4,6, 7,9,9b-heptaazaphenalene,
• 2,5-bis-[(4-(2-ethylhexyloxy)-2-hydroxy)-phenyl]-8-(4-methoxyphenyl)- 1 ,3,4,6, 7,9, 9b-heptaazaphenalene,
• 2-(2-ethylhexylamino)-5,8-bis-(4-(5-(1 ,1-dimethylpropyl)benzo[d]oxazol-2- yl)phenylamino)-1 , 3,4,6, 7,9,9b-heptaazaphenalene,
• 2,5,8-tris-(4-(1 H-pyrazol-1 -yl)phenylamino)-1 ,3,4,6, 7, 9,9b- heptaazaphenalene
• 2,5,8-tris-(4-benzoylphenylamino)-1 , 3,4,6, 7,9,9b-hepta azaphenalene,
• 2, 5,8-tris-(4-butoxy-2-hydroxyphenyl)-1 , 3,4,6,7, 9,9b-heptaazaphenalene, • 2,5,8-tris-(naphthalen-2-ylamino)-1 , 3,4,6,7, 9,9b-hepta azaphenalene,
• 2,5-bis-(4-(butoxycarbonyl)phenylamino)-8-(2-(1 -methyl-1 H-indol-3-yl)- 1 ,3,4,6, 7, 9,9b-heptaazaphenalene,
• 2,5,8-tris-(biphenyl-4-yloxy)-1 ,3,4,6,7,9,9b-heptaaza phenalene,
• 2,5,8-tris-(3-methoxyphenylamino)-1 , 3,4,6, 7,9,9b-hepta azaphenalene,
• 2,5,8-tris-(4-methoxyphenylamino)-1 , 3,4,6, 7,9,9b-hepta azaphenalene,
• 2,5,8-tris-(4-((E)-3-ethoxy-3-oxoprop-1 -enyl)phenyl amino)-1 ,3,4,6,7,9,9b- heptaazaphenalene,
• 2,5,8-tris-(methoxycarbonyl-4'-biphenyl-4-ylamino)-1 ,3, 4,6,7,9,9b- heptaazaphenalene,
• 2,5,8-tris-(4-(methoxycarbonyl)phenylamino)-1 ,3,4,6, 7,9,9b- heptaazaphenalene,
• 2,5,8-tris-(4-(1 H-benzo[d]imidazol-2-yl)-3-hydroxy phenylamino)- 1 ,3,4,6, 7,9, 9b-heptaazaphenalene,
• 2,5,8-tris-(4-(phenylamino)phenylamino)-1 ,3,4,6,7,9,9b-heptaazaphenalene,
• 2,5,8-tris-((4-(E)-styrylphenyl)amino)-1 ,3,4,6,7,9,9b-heptaazaphenalene,
• 2,5,8-tris-(2-ethylhexylamino)-1 , 3,4,6, 7,9,9b-heptaaza phenalene,
• 2,5,8-tris-(4-(L-menthylcarbonyl)phenylamino)-1 ,3,4,6, 7,9,9b- heptaazaphenalene,
• 2,5,8-tris-(4-((3,3,5-trimethylcyclohexyloxy)carbonyl) phenylamino)- 1 ,3,4,6,7,9,9b-heptaazaphenalene,
• 2,5,8-tris-(4-((E)-3-(2-ethylhexyloxy)-3-oxoprop-1 -enyl) phenylamino)- 1 ,3,4,6, 7, 9,9b-heptaazaphenalene,
• 2-(3-((E)-3-(2-ethylhexyloxy)-3-oxoprop-1 -enyl)phenyl amino)-5,8-bis-(4-((£)- 3-(2-ethylhexyloxy)-3-oxoprop-1-enyl)phenylamino)-1 ,3,4,6, 7, 9,9b- heptaazaphenalene,
• 2,5,8-tris-(3-nitrophenylamino)-1 , 3,4,6, 7,9,9b-heptaaza phenalene,
• 2,5,8-tris-(4-(2-butyloctyloxycarbonyl)phenylamino)-1 ,3, 4,6,7,9,9b- heptaazaphenalene,
• 2,5,8-tris-(4-(2-hexyldecyloxycarbonyl)phenylamino)-1 ,3, 4,6,7,9,9b- heptaazaphenalene,
• 2,5,8-tris-(4-(dodecyloxycarbonyl)phenylamino)-1 ,3,4, 6,7,9,9b- heptaazaphenalene,
• 2,5,8-tris-(4-(hexyldecyloxycarbonyl)phenylamino)-1 ,3,4, 6,7,9,9b- heptaazaphenalene,
• 2,5,8-tris-(4-(octyldecyloxycarbonyl)phenylamino)-1 ,3,4, 6,7,9,9b- heptaazaphenalene,
• 2,5,8-tris-((3-(E)-styrylphenyl)amino)-1 ,3,4,6,7,9,9b-heptaazaphenalene,
• 2,5,8-tris-(4-((3,5,5-trimethylhexyloxy)carbonyl phenyl amino)-1 , 3,4,6, 7,9, 9b- heptaazaphenalene,
• 2, 5-bis-(3-(methoxy)phenylamino)-8-(2-(1 -methyl-1 H-pyrrol-2-yl)- 1 ,3,4,6,7,9,9b-heptaazaphenalene,
• 2,5,8-tris-(4-((2-ethylhexyl)carbamoyl)phenylamino)-1,3, 4,6,7,9,9b- heptaazaphenalene,
• 2,5,8-tris-(4-(dodecyloxycarbonyl)phenylamino)-1,3,4,6,7,9,9b- heptaazaphenalene,
• 2,5,8-tris-(4-(1,3,3-trimethylbicyclo[2.2.1]heptan-2-yloxy)phenylamino)- 1,3,4,6,7,9,9b-heptaazaphenalene,
• 2,5,8-tris-(1H-indol-5-ylamino)-1 ,3,4,6,7,9,9b-heptaazaphenalene, • 2, 5,8-tris-(4-((3,7-dimethyloctyloxy)carbonyl)phenylamino)-1 ,3,4,6,7,9,9b- heptaazaphenalene and
2,5,8-tris-(2-amino-4,5-dimethylphenylamino)-1 ,3,4,6,7,9,9b- heptaazaphenalene;
and/or at least one of its stereoisomers, preferably enantiomers or diastereomers, a racemate or a mixture of at least two of its stereoisomers, preferably enantiomers and/or diastereomers in any mixing ratio, or at least one physiologically acceptable salt thereof, or at least one corresponding solvate thereof.
14. A light-stabilized composition according to anyone one of the preceding claims 1 to 13, characterized in that the light-stabilizing component comprises at least one further light stabilizer (Z) selected from the group comprising acrylate derivatives, allantoin derivatives, aminobenzoic acid derivatives, aminobenzamides derivatives, anthranilic acid derivatives, benzalmalonic acid derivatives, benzimidazole derivatives, benzoate derivatives, benzophenone derivatives, benzopyranone derivatives, benzothiazole derivatives, benzotriazole derivatives, benzoxazinone derivatives, benzoxazole derivatives, camphor derivatives, cinnamate derivatives, coumarinic acid derivatives, curcumin derivatives, cycloaliphatic ketone derivatives, dianisoylmethane derivatives, dibenzalazine derivatives, dibenzoylmethane derivatives, dioxane derivatives, ferulic acid derivatives, formamidine derivatives, formanilides, furane derivatives, glutamic acid derivatives, hindered amine derivatives, imidazoline derivatives, inorganic pigments, malonic acid derivatives, metal oxides, metal dioxides, nicotinic acid derivatives, nitrobenzamides derivatives, nitrobenzoic acid derivatives, nucleic acid derivatives, oxamide derivatives, oxanilide derivatives, p-aminobenzoic acid (PABA) derivatives, plant extracts, aromatic propanedione derivatives, propenoate derivatives, pyrimidine derivatives, quenchers, salicylate derivatives, tetrazole derivatives, triazine derivatives, tributamine derivatives, urocanic acid derivatives and vitamin Be derivatives.
15. A light-stabilized composition according to claim 14, characterized in that the light-stabilizing component comprises as further light stabilizer (Z) at least one compound of general formula (X)
Figure imgf000131_0001
(X)
wherein
R1x represents a hydrogen atom; an optionally substituted cycloalkyl radical from 3 to 7 carbon atoms; an aryl radical which is unsubstituted or at least mono-substituted with a group selected from aryl, halogen, an -O-C-i-β radical and a Ci_6 alkyl radical; a -phenyl-Ci.6 alkyl radical; a linear or branched C-i-s alkyl radical which is unsubstituted or at least mono-substituted with a moiety selected from -SO3MX, -N(R4x)3 + and a radical of general formula (XX)
Figure imgf000131_0002
(XX) wherein
y = O or 1 ; z = 0, 1 , 2, 3 or 4;
R5x, R6x, R7x, R8x and R9x, independent of each other, each represents an unsubstituted or at least mono-substituted Ci-β alkyl radical; an -O-Ci-6 radical; an unsubstituted or at least mono-substituted aryl radical and an -OSi(R10x)3 radical;
R >10x represents a d-6 alkyl radical; an -O-d-6 radical; or an unsubstituted or at least mono-substituted aryl radical;
M represents a hydrogen atom, Na + o _ _r K IX+. ;
R4x represents an unsubstituted or at least mono-substituted C-ι-6 alkyl radical;
R2x and R3x, independent of each other, each represents a hydrogen atom; an unsubstituted or at least monosubstituted Ci-4 alkyl radical; or an unsubstituted or at least mono-substituted aryl radical;
A1x represents a radical of general formula (X1 ) or (X2)
Figure imgf000132_0001
A ^ 2xx represents a radical of general formula (X1 ), (X3) or (X4)
Figure imgf000132_0002
(X1 ) (X3) (X4)
wherein R11x represents a hydrogen atom; a linear or branched, saturated or unsaturated, unsubstituted or at least monosubstituted C-ι-6 aliphatic radical; or a hydroxy (-OH) residue;
R12x represents a hydrogen atom; a -C(=O)-OR15x radical; a -C(=O)-NR16xR17x radical; an unsubstituted or at least monosubstituted -O-C-i.-iβ radical; an unsubstituted or at least monosubstituted -O-phenyl radical; a Cs-7 cycloalkyl radical; a phenyl or a naphtyl radical; a phenyl or a naphtyl radical which are substituted by 1 or 2 substituents which are independently from one another selected from the group consisting of phenyl, Cl, -0-Ci-6 alkyl and Ci-6 alkyl; a linear or branched, saturated or unsaturated Ci--I8 aliphatic radical which is unsubstituted or at least mono-substituted with -OH, -phenyl or un moiety of general formula (XX) as defined above;
pi5χ Ri6χ anc| pji7x independent of each other, each represents a hydrogen atom; a linear or branched, unsubstituted or at least mono-substituted CMS alkyl radical;
R14x represents hydrogen atom; or -SO3MX, with Mx being H, Na+ or K+;
R13x and Rl13x, independent of each other, each represents a hydrogen atom; an unsubstituted or at least monosubstituted C(=O)-Ci-i8 radical; a linear or branched CMS alkyl radical, which is unsubstituted or at least mono- substituted with at least one hydroxy (-OH) residue, a SO3MX moiety, a - N(R4x)3 + moiety, wherein Mx and R4x have the meaning as defined above, or a radical of general formula (XX) as defined above;
and/or
at least one compound of general formula (Is)
Figure imgf000134_0001
(Is) wherein
ns= 0, 1 , 2, 3 or 4;
R1s represents a hydrogen atom; a linear or branched, unsubstituted or at least monosubstituted Ci-3 alkyl radical; or a R2sR3s "substituted phenyl- radical;
R2s, R2s , R3s and R3s , independent of each other, each represents a hydrogen atom; a halogen atom; a hydroxy (-OH) residue; an unsubstituted or at least monosubstituted C-ι-3 alkyl radical; an unsubstituted or at least monosubstituted -O-C-i-3 radical; or an unsubstituted or at least monosubstituted aryl radical;
or
R2s and R3s form together with the phenyl ring to which they are attached, an unsubstituted or at least mono-substituted naphthalene ring;
R4s and R5s, independent of each other, each represents a hydrogen atom; an unsubstituted or at least monosubstituted Ci-4 alkyl radical; or an unsubstituted or at least mono-substituted aryl radical;
A1s represents a radical of general formula (Ms), (Ills) or (IVs)
Figure imgf000135_0001
A v 2s represents a radical of general formula (Ms) or (Vs)
Figure imgf000135_0002
wherein
R >6s represents a hydrogen atom; a linear or branched, unsubstituted or at least monosubstituted Ci-6 alkyl radical; or a hydroxy (-OH) residue;
R7s represents a hydrogen atom; an unsubstituted or at least monosubstituted, saturated or unsaturated, C3-6 cycloalkyl radical; an unsubstituted or at least monosubstituted, saturated or unsaturated C5-10 cycloalkyl radical, which contains 1 , 2 or 3 heteroatom(s) as ring member(s) independently selected from the group consisting of O, N and S; an unsubstituted or at least monosubstituted aryl radical; an unsubstituted or at least monosubstituted Cs- 10 heteroaryl radical which contains 1 , 2 or 3 heteroatom(s) as ring member(s) independently selected from the group consisting of O, N and S; a -C(=O)- OR11s radical; a -C(=O)-NR12sR13s radical; an unsubstituted or at least monosubstituted -O-C1-18 radical; an unsubstituted or at least monosubstituted -O-phenyl or -O-naphtyl radical; an unsubstituted or at least monosubstituted - COR14s radical; a linear or branched, saturated or unsaturated, CMS aliphatic radical, which is unsubstituted or at least mono-substituted with at least one hydroxy (-OH) residue, a SO3MS moiety, a -N(R15s)3 + moiety or a radical of general formula (VIs)
Figure imgf000136_0001
(VIs) wherein
ms = 0 or 1 ; ps = 0, 1 , 2, 3 or 4;
R i6s R i7s R i8s R i9s and R 20s jn(jepenc|ent of each other, each represents an unsubstituted or at least mono-substituted C-ι-6 alkyl radical; an unsubstituted or at least mono-substituted -O-Ci-6 radical; an unsubstituted or at least mono- substituted aryl radical; or an -O-Si(R21s)3 radical;
R21s represents an unsubstituted or at least mono-substituted Ci-6 alkyl radical; an -O-C1-6 radical; an unsubstituted or at least mono-substituted aryl radical;
R >11s , R D12s and R )13s , independent of each other, each represents a hydrogen atom; a linear or branched, unsubstituted or at least monosubstituted CMS alkyl radical; an unsubstituted or at least mono-substituted C3-6 cycloalkyl radical;
or
R12s and R13s form together with the bridging nitrogen atom an unsubstituted or at least mono-substituted, saturated 5 to 7-membered cycloaliphatic radical, which contains 1 , 2 or 3 heteroatom(s) as ring member(s) independently selected from the group consisting of O1 N and S; R14s represents an unsubstituted or at least mono-substituted C-Mβ alkyl radical; or an unsubstituted or at least mono-substituted aryl radical;
R15s represents an unsubstituted or at least mono-substituted C-MS alkyl radical;
Ms represents H, Na+ or K+;
R6s and R7s form together with the phenyl ring an unsubstituted or at least mono-substituted 9 to 15-membered polycyclic ring system;
or
R6s and R14s form together with the phenyl ring an unsubstituted or at least mono-substituted 9 to 15-membered polycyclic ring system;
R8s and R9s, independent of each other, each represents a hydrogen atom; an unsubstituted or at least monosubstituted -C(=O)-Ci.i8 radical; a linear or branched, saturated or unsaturated C-M8 aliphatic radical, which is unsubstituted or at least mono-substituted with at least one hydroxy (-OH) residue, a -SO3Nf moiety, a -N(R15s)3 + moiety or a radical of general formula (VIs) as defined above;
R1Os represents a hydrogen atom; or a -SO3MS moiety with Ms representing H, Na+ or K+;
and/or
at least one compound of general formula (L1 )
Figure imgf000138_0001
wherein W9 represents an alkyl or an arylcyanoacrylalkyl radical; W10 represents H1 a phenyl or an alkylindoline radical; and W11 represents H or a phenyl radical;
and/or
at least one compound of formula (L2)
Figure imgf000138_0002
(L2)
and/or
at least one compound of general formula (L3)
Figure imgf000138_0003
(L3) wherein Rm represents a linear or branched, unsubstituted or at least mono- substituted C-1-18 alkyl radical, a phenyl radical, an unsubstituted or at least mono-substituted hydroxyphenyl radical or a hydroxyalkylether; Rπ represents H, -OH, a linear or branched, unsubstituted or at least mono-substituted Ci-I8 alkyl radical, a hydroxy(alkylether)amino radical; R0 represents H, -OH or a linear or branched, unsubstituted or at least mono-substituted C-M8 alkyl radical; and Rp represents H or a linear or branched, unsubstituted or at least mono-substituted CMS alkyl radical;
and/or
at least one compound of general formula (L4)
Figure imgf000139_0001
(L4) wherein Rh represents -OH, an unsubstituted or at least mono-substituted alkoxy radical, an alkenoic acid alkoxyester radical, an aryloxy radical, a hydroxyalkoxy radical, a hydroxy(alkylether)alkoxy radical, a (polymerized acrylo)alkoxyester radical or an o-alkyl acid ester radical; R' represents H, SO3H or SOaNa; Rj represents H or -OH; Rk represents H, -OH or an an unsubstituted or at least mono-substituted alkoxy radical; and R1 represents H Or SO3Na;
and/or
at least one compound of general formula (L5)
Figure imgf000140_0001
wherein Ra and Rb represent -OH;
and/or
at least one compound of general formula (L6)
Figure imgf000140_0002
(L6) wherein Rd represents -OH; Re represents a linear or branched, unsubstituted or at least mono-substituted CMS alkyl radical, an hydroxyalkyl radical, an unsubstituted or at least mono-substituted acryloxyalkyl radical, an unsubstituted or at least mono-substituted (hydroxyphenyl)alkyl radical, an unsubstituted or at least mono-substituted (alkylester)alkyl radical, an unsubstituted or at least mono-substituted (hydroxyalkylether)oxoalkyl radical or an unsubstituted or at least mono-substituted phenylalkyl radical; R9 represents H or a linear or branched, unsubstituted or at least mono- substituted Ci-18 alkyl radical; and Rf represents Cl, Br or I;
and/or
at least one compound of formula (L7)
Figure imgf000141_0001
(L7)
and/or
at least one compound of general formula (L8)
Figure imgf000141_0002
(L8) wherein Rs represents a linear or branched, unsubstituted or at least mono- substituted Ci-18 alkyl radical; Rv represents an alkylester or a cyano moiety; R1 represents a hydrogen atom or a phenyl radical and Ru represents a hydrogen atom or an -O-Ci.i8 radical;
and/or
at least one compound of general formula (L9)
Figure imgf000142_0001
wherein W3, W4, W5 and W6, independent from each other, each represents a linear or branched, unsubstituted or at least mono-substituted C-MS alkyl radical
and/or
at least one compound of general formula (L10)
Figure imgf000142_0002
wherein Rr and Rq represent a linear or branched, unsubstituted or at least mono-substituted CMS alkyl radical;
and/or
Figure imgf000142_0003
(L11 ) wherein W7 represents a hydrogen atom, a formanilide moiety, an unsubstituted or at least mono-substituted alkylalkoxy radical and/or contains a benzimidazole radical and W8 represents a linear or branched, unsubstituted or at least mono-substituted C1--Ie alkyl radical;
and/or
at least one compound of general formula (L12)
Figure imgf000143_0001
(L12) wherein W1 represents an unsubstituted or at least mono-substituted -O-Ci-iβ alkyl radical and W1 represents a linear or branched, unsubstituted or at least mono-substituted CMS alkyl radical;
and/or
at least one compound of general formula (L13)
Figure imgf000143_0002
(L13) wherein Rc represents a linear or branched, unsubstituted or at least mono- substituted C1-18 alkyl radical or an unsubstituted or at least mono-substituted, saturated or unsubstituted cycloalkyl radical; and/or
at least one compound of general formula (L14)
Figure imgf000144_0001
(L14) wherein W12 represents a hydrogen atom or -OH; W13 represents a hydrogen atom, an unsubstituted or at least mono-substituted -0-Ci-1S alkyl radical or an unsubstituted or at least mono-substituted hydroxyalkoxy radical; W14 represents a hydrogen atom or a linear or branched, unsubstituted or at least mono-substituted C1-Ie alkyl radical; W15 represents a hydrogen atom, a linear or branched, unsubstituted or at least mono-substituted C1-1S alkyl radical or an unsubstituted or an at least mono-substituted alkylester radical; W16 represents a hydrogen atom or a linear or branched, unsubstituted or at least mono- substituted C1-18 alkyl radical and W17 represents a linear or branched, unsubstituted or at least mono-substituted C1-18 alkyl radical or an at least mono-substituted alkylester radical;
and/or at least one of the stereoisomers, preferably enantiomers or diastereomers, a racemate or a mixture of at least two of the stereoisomers, preferably enantiomers and/or diastereomers in any mixing ratio, or at least one physiologically acceptable salt and/or at least one corresponding solvate of the aforementioned compounds of general formulae (X)1 (Is), (L1 ), (L3), (L4), (L5), (L6), (L8), (L9), (L10), (L11 ), (L12), (L13) and (L14).
16. A light-stabilized composition according to claim 14 or 15, characterized in that that the further light stabilizer (Z) is at least one compound selected from the group comprising isooctyl α-cyano-β, β-di-phenylacrylate, methyl α- carbomethoxycinnamate, methyl α-cyano-β-methyl-p-methoxycinnamate, butylα-cyano-β-methyl-p-methoxy-cinnamate, methyl α-carbomethoxy-p- methoxycinnamate, N-(β-carbomethoxy-β-cyanovinyl)-2-methylindoline, ethyl-2- cyano-3,3-diphenylacrylate (UVINUL® 3035); 2-ethylhexyl-2-cyano-3,3- diphenylacrylate (UVINUL® 3039); 1 ,3-bis-[(2'-cyano-3,3'-diphenylacryloyl)oxy]- 2,2-bis-{[(2-cyano-3',3'-di- phenylacryloyl)oxy]methyl}propane (UVINUL® 3035); 2-cyano-3-(2-methylindolin- yl) methylacrylate (UV Absorber Bayer 340); 2- phenyl-1 H-benzimidazole-5-sulfonic acid (GIVSORB® UV-16); dibenzoyl resorcinol, bis(4-tert-butylbenzoyl) resorcinol, benzoyl resorcinol, 2,4-di- tertbutylphenyl 3,5-di-tert-butyl-4-hydroxybenzoate, hexadecyl 3,5-di-tert-butyl- 4-hydroxybenzoate, octadecyl 3,5-di-tert-butyl-4-hydroxybenzoate, 2-methyl- 4,6-di-tert-butylphenyl 3,5-di-tert-butyl-4-hydroxybenzoate, hexadecyl 3,5-di-t- butyl-4-hydroxybenzoate (CYASORB® UV 2908); 3-hydroxyphenylbenzoate (SEESORB® 300); ethyl-4-[[(ethylphenylamino)methylene]amino]benzoate (GIVSORB® UV-1); phenyl 2-hydroxybenzoate or phenylsalicylate (SEESORB® 201 ); 2,4-di-t-butylphenyl-3,5-di-t-butyl-4-hydroxybenzoate (TINUVIN® 120); 4- bis(polyethoxy)amino acid polyethoxy ethyl ester (UVINUL® P 25); 4-t- butylphenyl 2-hydroxybenzoate, 2-hydroxy-4-octyloxybenzophenone (UVINUL® 3008); 2-hydroxy-4-methoxybenzophenone (UVINUL® 3040); 2-hydroxy-4- methoxy-5-sulfobenzophenone or sulisobenzone (UVINUL® MS 40); 2-(4- Benzoyl-3-hydroxyphenoxy)-2-propenoic acid ethyl ester (CYASORB® UV 2098); homopolymer of 4-(2-acryloyloxyethoxy)-2-hydroxybenzophenone (CYASORB® UV 2126); 2,2'-dihydroxy-4-methoxybenzophenone or dioxybenzone (CYASORB® UV 24); 2-hydroxy-4-(2-hydroxy-3- decyloxypropoxy)benzophenone, 2-hydroxy-4-(2-hydroxy-3- octyloxypropoxy)benzophenone (MARK 1535); 2,4,4'-trihydroxybenzophenone (MAXGARD 200); 2-hydroxy-4-(isooctyloxy) benzophenone (MAXGARD 800); 2-hydroxy-4-dodecyloxybenzophenone (UVINUL® 410); 2,2I-dihydroxy-4,41- dimethoxy-5,5'-disulfobenzophenone, disodium salt (UVINUL® 3048); 2,4- dihydroxybenzophenone (UVINUL® 400); 2,2'-dihydroxy-4,4I- dimethoxybenzophenone (UVINUL® D 49); 2,2',4,41-tetrahydroxybenzophenone (UVINUL® D 50); 2,21-dihydroxy-4-(2-hydroxyethoxy)benzophenone (UVINUL® X-19); 2-hydroxy-4-benzyloxybenzophenone (SEESORB® 105); 2-hydroxy-4- hydroxybenzophenone, 2-hydroxy-4-decyloxybenzophenone, 2-hydroxy-4,2',4'- trihydroxybenzophenone, 2-hydroxy-4-(octyloxy)benzophenone (CHIMASSORB® 81 ); 2-hydroxy-21-hydroxy-4,4'-dimethoxybenzophenone, 3,3',4',5,7-pentahydroxyflavone, quercetin, 2-(2H-benzotriazol-2-yl)-6-dodecyl-4- methyl-phenol, methyl 3-(3-(2H-benzotriazole-2-yl)-5-t-butyl-4-hydroxyphenyl) propionate/PEG 300 (TINUVIN® 213); 6-tert-butyl-2-(5-chloro-2H-benzotriazole- 2-yl)-4-methylphenol (UVINUL® 3026); 6-tert-butyl-2-(5-chloro-2H- benzotriazole-2-yl)-4-methylphenol (UVINUL® 3027); 2,4-di-tert-butyl-6-(5- chloro-2H-benzotriazole-2-yl)-phenol (UVINUL® 3028); 2-(2H-benzotriazole-2- yl)-4-(1 ,1 ,3,3-tetramethylbutyl)-phenol (UVINUL® 3029); 2-(2H-benzotriazole-2- yl)-4-methylphenol (UVINUL® 3033 P); 2-(2H-benzotriazole-2-yl)-4,6-bis(1- methyl-1-phenylethyl)phenol (UVINUL® 3034); 2-(2'-hydroxy-5'-(2- hydroxyethyl))benzotriazole (NORBLOC 6000); 2-(2'-hydroxy-5'- methacrylyloxyethylphenyl)-2H-benzotriazole (NORBLOC 7966); 1 ,1 ,1- tris(hydroxyphenyl) ethane benzotriazole (THPE BZT); 5-t-butyl-3-(5-chloro-2H- benzotriazol-2-yl)-4-hydroxybenzenepropanoic acid octyl ester, 3-(5-chloro-2H- benzotriazol-2-yl)-5-t-butyl-4-hydroxybenzenepτopanoic acid octyl ester (TINUVIN® 109); a-[3-[3-(2H-benzotriazol-2-yl)-5-t-butyl-4-hydroxyphenyl]-1- oxopropyl]-w-hydroxypoly(oxy-1 ,2-ethane-diyl), a-[3-[3-(2H-benzotriazol-2-yl)-5- t-butyl-4-hydroxyphenyl]-1-oxopropyl]-w-[3-[3-(2H-benzotriazol-2-yl)-5-t-butyl-4- hydroxyphenyl]-1-oxopropoxy]poly(oxy-1 ,2-ethanediyl) (TINUVIN® 1130); 2-(2- hydroxy-3,5-di-t-butylphenyl) benzotriazole (TINUVIN® 320); 2-(2-hydroxy-3-t- butyl-5-methylphenyl)-5-chloro-2H-benzotriazole (TINUVIN® 326); 2-(3'-5'-di-t- butyl-2'-hydroxyphenyl-)-5-chlorobenzotriazole (TINUVIN® 327); 2-(2-hydroxy- 3,5-di-t-amylphenyl)benzotriazole (TINUVIN® 328); 2-(2H-benzotriazol-2-yl)-4- (1 ,1 ,3,3-tetramethylbutyl)phenol (TINUVIN® 329); 3-(2H-Benzotriazol-2-yl)-5-t- butyl-4-hydroxybenzenepropanoic acid (TINUVIN® 384); 2-(2H-benzotriazol-2- yl)-4-methyl-6-dodecylphenol (TINUVIN® 571 ); 3-(2H-benzotriazol-2-yl)-5-t- butyl-4-hydroxy-1 ,6-hexanediyl ester of benzenepropanoic acid, 3-(2H- benzotriazol-2-yl)-5-t-but-yl-4-hydroxy-methyl ester of benzenepropanoic acid (TINUVIN® 840); 2-[2-hydroxy-3I5-bis-(1 ,1-dimethylbenzyl) phenyl]-2H- benzotriazole (TINUVIN® 900); 2-(2H-benzotriazol-2-yl)-6-(1-methyl-1- phenylethyl)-4-(1,1 ,3- ,3-tetramethylbutyl) phenol (TINUVIN® 928); 3-(2H- benzotriazol-2-yl)-5-t-butyl-4-hydroxybenzenepropanoic acid, C7-9 branched and linear alkyl esters (TINUVIN® 99); 2-(2H-benzotriazol-2-yl)-p-cresol (TINUVIN® P); 2-(2'-hydroxy-3'-sec-butyl-5'-t-butylphenyl) benzotriazole (TINUVIN® 350); 2- (2'-hydroxy-5'-t-butylphenyl) benzotriazole (TINUVIN® PS); 2,2'-methylenebis(6- (2H-benzotriazol-2-yl)-4-1 ,1 ,3,3-tetramethylbutyl)phenol (TINUVIN® 360); 2- (2H-benzo[d][1 ,2,3]triazol-2-yl)-4,6-bis(2-phenylpropan-2-yl)phenol (TINUVIN® 234); TINUVIN® B 75; 2,2'-(p-phenylene) di-3,1-benzoxazin-4-one (CYASORB® 3638); dimethyl(p-methoxybenzylidene)malonate (SANDUVOR® PR 25); 3-(4- methoxyphenyl)-2-propenoic acid 2-ethylhexyl ester, octyl p-methoxycinnamate, 3-(4-methylbenzylidene)-D,L-camphor (GIVSORB® UV-15); ethyl-4- [[(methylphenylamino)methylene]amino]benzoate (GIVSORB® UV-2, TINUVIN® 101 ); N-(2-ethoxyphenyl)-N'-(4-isododecylphenyl) oxamide (SANDUVOR 3206); N-[5-t-butyl-2-ethoxyphenyl)-N'-(2-ethylphenyl) oxamide (TINUVIN® 315); N-(2-ethoxyphenyl)-N'-(2-ethylphenyl) oxamide (TINUVIN® 312); 2H-benzimidazole-2-carboxylic acid (4-ethoxyphenyl) amide (UVINUL® FK 4105); 4,41-dioctyloxyoxanilide, 2,2'-diethoxyoxanilide, 2,2'-dioctyloxy-5,5'-di- tert-butoxanilide, 2,2'-didodecyloxy-5,51-di-tert-butoxanilide, 2-ethoxy-2'- ethyloxanilide, N,N'-bis(3-dimethylaminopropyl)oxamide, 2-ethoxy-5-tert-butyl- 2'-ethoxanilide, bis(2,2,6,6-tetramethyl-4-piperidyl)sebacate (TINUVIN® 770); N,N'-bis(2,2,6,6-tetramethyl-4-piperidyl)- N,N'-hexamethylenebis(formamide) (UVINUL® 4050H); polymer of 2,2,4,4-tetxamethyl-7-oxa-3,20-diaza-20-(2,3- epoxi-propyl)-dispiro-(5.1.11.2)-heneicosane-21-one (HOSTAVIN® N 30); bis(2,2,6,6-tetramethyl-1-(octyloxy)-4-piperidinyl) decanedioic acid ester (TINUVIN® 123); ester of [(4-methoxyphenyl)methylene]-, bis(1 , 2,2,6,6- pentamethyl-4-piperidinyl)propanedioic acid (SANDUVOR® PR-31 ); copolymer of dimethlylester of 4-hydroxy-2,2,6,6-tetramethyl-1-piperaidine ethanol butanedioic acid (TINUVIN® 622) and bis(2,2,6,6-tetramethyl-4- piperidyl)sebacate (TINUVIN® 783); i .r.r-Cl .a.S-triazine^Aβ- triyltris((cyclohexylimino)-2,1-eth- anediyl) tris(3,3,4,5,5- pentamethylpiperazinone (GOODRITE® UV 3159); 1 ,6-Hexanediamine, N, N'- bis(2,2,6,6-tetramethyl-4-piperidinyl)-polymer with 2F4,6-trichloro-1 ,3,5-triazine, reaction products with N-butyl-1-butanamine an N-butyl-2,2,6,6-tetramethyl-4- piperidinamine (CHIMASSORB® 2020); polymethylpropyl-3-oxy-4(2,2,6,6- tetramethyl)p- iperidinyl)siloxane (UVASIL® 299); bis(2,2,6,6-tetramethyl-4- piperidyl)succinate, bis(1 ,2,2,6,6-pentamethyl-4-piperidyl)sebacate, bis(1- octyloxy-2,2,6,6-tetramethyl-4-piperidyl)sebacate, poly[[6-[(1 ,1 ,3,3,- tetramethylbutyl)amino]-1 ,3,5-triazine-2,4-diyl][(2,2,6,6-tetramethyl-4- piperidinyl)imino]-1 ,6-hexanediyl[(2,2,6,,6-tetramethyl-4-piperidinyl)imino]]) (CHIMASSORB® 944); bis(1 ,2,2,6,6-pentamethyl-4-piperidyl) n-butyl-3,5-di-tert- butyl-4-hydroxybenzylmalonate; the condensate of 1-(2-hydroxyethyl)-2,2,6,6- tetramethyl-4-hydroxypiperidine and succinic acid; the condensate of N1N1- bis(2,2,6,6-tetramethyl-4-piperidyl)hexamethylenediamine and 4-tert-octylamino- 2,6-dichloro-1 ,3,5-triazine, tris(2,2,6,6-tetramethyl-4-piperidyl)nitrilotriacetate; tetrakis(2,2,6,6-tetramethyl-4-piperidyl)-1 ,2,3,4-butane-tetracarboxylate, 1 ,1'- (1 ,2-ethanediyl)bis(3,3,5,5-tetramethylpiperazinone), 4-benzoyl-2,2,6,6- tetramethylpiperidine, 4-stearyloxy-2,2,6,6-tetramethylpiperidine, bis(1 ,2,2,6,6- pentamethylpiperidyl)-2-n-butyl-2-(2-hydroxy-3,5-di-tert-butylbenzyl)malonate, 3- n-octyl-7,7,9,9-tetramethyl-1 ,3,8-triazaspiro[4.5]decan-2,4-dion, bis(1 -octyloxy- 2,2,6,6-tetramethylpiperidyl)sebacate, bis(1 -octyloxy-2, 2,6,6- tetramethylpiperidyl)succinate, the condensate of N,N'-bis-(2,2,6,6-tetramethyl- 4-piperidyl)hexamethylenediamine and 4-morpholino-2,6-dichloro-1 ,3,5-triazine; the condensate of 2-chloro-4,6-bis(4-n-butylamino-2,2,6,6-tetramethylpiperidyl)- 1 ,3,5-triazine and 1 ,2-bis(3-aminopropylamino)ethane; the condensate of 2- chloro-4,6-di-(4-n-butylamino-1 ,2,2,6,6-pentamethylpiperidyl)-1 ,3,5-triazine and 1 ,2-bis-(3-aminopropylamino)ethane; 8-acetyl-3-dodecyl-7,7,9,9-tetramethyl- 1 ,3,8-triazaspiro[4.5]decane-2,4-dione, 3-dodecyl-1 -(2,2,6,6-tetramethyl-4- piperidyl)pyrrolidin-2,5-dione, 3-dodecyl-1-(1 ,2,2,6,6-pentamethyl-4- piperidyl)pyrrolidine-2,5-dione, a mixture of 4-hexadecyloxy- and 4-stearyloxy- 2,2,6,6-tetramethylpiperidine; a condensation product of N,N'-bis(2,2,6,6- tetramethyl-4-piperidyl)hexamethylenediamine and 4-cyclohexylamino-2,6- dichloro-1 ,3,5-triazine; N-(2,2,6,6-tetramethyl-4-piperidyl)-n-dodecylsuccinimid, N-(1, 2,2,6, e-pentamethyl^-piperidylj-n-dodecylsuccinimid, 2-undecyl-7,7,9,9- tetramethyl-1-oxa-3,8-diaza-4-oxo-spiro[4,5]decane, a reaction product of 7,7,9,9-tetramethyl-2-cycloundecyl-1 -oxa-3,8-diaza-4-oxospiro [4,5]decane and epichlorohydrine, titanium dioxide, zinc oxide, zinc cerium oxide, carbon black, cadmium sulfide, cadmium selenide, chromium oxide, iron oxide, lead oxide, zirconium oxide, bis (1 ,2,2,6,6-pentamethyl-4-piperidinyl)-2-butyl-2-(4-hydroxy- 3,5-di-tert.-butylbenzyl)propanedioate (TINUVIN® 144); 4-t-butyl-4'- methoxydibenzoylmethane, avobenzone (GIVSORB® UV-14); nickel dibutyldithiocarbamate; thio bis2,2'-[4-(1 ,1 ,3,3-tetramethylbutyl)-phenyl- Jnickel- 2-ethyl hexanoate; n-butylamine-nickel-2,2'-thio bis(4-t-octylphenolate), nickel- bis-[2,2'-thio bis(4-t-octylphenolate)], octylphenyl salicylate, 4-t- butylphenylsalicylate (SEESORB® 202); S.S.δ-trimetylcyclohexylsalicylate or homomentyylsalicylate (NEO HELIOPAN HMS); menthyl-o-aminobenzoate (NEO HELIOPAN MA); 2-[4,6-bis(2,4-dimethylphenyl)-1 ,3,5-triazin-2-yl]-5- octyloxyphenol (CYASORB® UV 1164); confidential triazine derivative (TINUVIN® 1545); 2-(4,6-diphenyl-1 ,3,5-triazin-2-yl)-5-hexyloxyphenol (TINUVIN® 1577 FF); 2-[4-((2-hydroxy-3-dodecyloxypropyl)oxy)-2- hydroxyphenyl]-4,6-bis(2,4-dimethylphenyl)-1 ,3,5-triazine (TINUVIN® 400); 2,4,6-Trianilino-p-(carbo-2I-ethylhexyl-1'-oxy)-1 ,3,5-triazine (UVINUL® T-150); 2, 4-bis(2, 4-dihydroxyphenyl)-6-(1-methyl-1 H-pyrazol-5-yl)-1 ,3,5-triazine, 2,4- bis{[4-(2-ethylhexyloxy)-2-hydroxy]phenyl}-6-(1 -methyl-1 H-pyrazol-5-yl)-1 ,3,5- triazine, 2-[2, 4-bis (2-ethylhexyloxy)phenyl]-4-[4-(2-ethylhexyloxy)-2- hydroxyphenyl]-6-(1 -methyl-1 H-pyrazol-5-yl)-1 , 3, 5- triazine, 2,4-bis(2, 4- dihydroxyphenyl)-6(1-phenyl-1 H-pyrazol-5-yl)-1 ,3,5-triazine, 2,4-bis{[4-(2- ethylhexyloxy)-2-hydroxy]phenyl}-6-(1 -phenyl-1 H-pyrazol-5-yl)-1 ,3,5-triazine, 2,4-bis [4-(butoxycarbonyl)phenylamino]-6-(1 -methyl-1 H-pyrazol-5-yl)-1 ,3,5- triazine, 2,4-bis{4-[(2-(ethylhexyloxy)carbonyl]phenylamino}-6-(1 -methyl-1 H- pyrazol-5-yl)-1 ,3,5-triazine, 2,4-bis [4-(butoxycarbonyl)phenylamino]-6-(1- phenyl-1 H-pyrazol-5-yl)-1 ,3,5-triazine, 2,4-bis{4-[(2- ethylhexyloxy)carbonyl]phenylamino}-6-(1 -phenyl-1 H-pyrazol-5-yl)-1 ,3,5- triazine, 2-[(4-butoxycarbonyl)phenylamino]-4,6-bis( 1 -methyl-1 H-pyrazol-5-yl)- 1 ,3,5-triazine, 2-(1-benzyl-1 H-pyrrol-2-yl)-4,6-bis(2,4-dihydroxyphenyl)-1 ,3,5- triazine, 2-(1 -benzyl-1 H-pyrrol-2-yl)-4,6-bis[4-(2-ethylhexyloxy)-2- hydroxyphenyl]-1 ,3,5-triazine, 2-(1 -benzyl-1 H-pyrrol-2-yl)-4,6-bis[4- (butoxycarbonyl) phenylamino]-1 ,3,5-triazine, 2-(1 -benzyl-1 H-pyrrol-2-yl)-4,6- bis(biphenyl-4-ylamino)-1 ,3,5-triazine, 2-(1 -benzyl-1 H-pyrrol-2-yl)-4,6-bis(4- benzoylphenylamino)-1 ,3,5-triazine, 2-(1 -benzyl-1 H-pyrrol-2-yl)-4,6-bis(9-oxo- 9H-fluoren-3-ylamino)-1 ,3,5-triazine, 2-(1 -benzyl-1 H-pyrrol-2-yl)-4,6-bis[4- (imidazo[1 ,2-a]pyridin-2-yl)phenylamino]-1 ,3,5-triazine, 2-(1-benzhydryl-1 H- pyrrol-2-yl)-4,6-bis[4-(butoxycarbonyl)phenylamino]-1 ,3,5-triazine, 2-(1 -benzyl- 1 H-pyrrol-2-yl)-4,6-bis[4-(6,6-dimethyl-4-oxo-4,5,6,7-tetrahydroindol-1- yl)phenylamino]-1 ,3,5-triazine, 2-(1-benzyl-1 H-pyrrol-2-yl)-4,6-bis[4-((2- ethylhexyloxy)carbonyl)phenylamino]-1 ,3,5-triazine, 2-(1-benzyl-1 H-pyrrol-2-yl)- 4,6-bis[4-1 H-imidazo[1 ,2-a]pyridin-2-yl)phenylamino]-1 ,3,5-triazine, 2-(1-benzyl- 1 H-pyrrol-2-yl)-4,6-bis[4-(1 H-benzo[d]imidazol-2-yl)phenylamino]-1 ,3,5-triazine, 2-(1-benzyl-1 H-pyrrol-2-yl)-4,6-bis[4-(1 H-pyrazol-1-yl)phenylamino]-1 ,3,5- triazine, 2-(1-benzyl-1 H-pyrrol-2-yl)-4,6-bis[naphthalen-2-ylamino]-1 ,3,5-triazine, 2-(1 -benzyl-1 H-pyrrol-2-yl)-4,6-bis[4-((E)-3-ethoxy-3-oxoprop-1 - enyl)phenylamino]-1 ,3,5-triazine and 2-(1 -benzyl-1 H-pyrrol-2-yl)-4,6-bis[4-(E)- styrylphenylamino]-1 ,3,5-triazine;
and/or at least one of the stereoisomers, preferably enantiomers or diastereomers, a racemate or a mixture of at least two of the stereoisomers, preferably enantiomers and/or diastereomers in any mixing ratio, or at least one physiologically acceptable salt and/or at least one corresponding solvate of the aforementioned compounds.
17. A light-stabilized composition according to claim 14, characterized in that that the further light stabilizer (Z) is at least one compound selected from the group comprising 2-ethylhexyl 2-cyano-3,3'-diphenylacrylate, ethyl 2-cyano-3,3'- diphenylacrylate, polymer of N-{(2 and 4)[(2-oxoborn-3- ylidene)methyl]benzyl}acrylamide, methyl 4-aminobenzoate, butyl 4- aminobenzoate, 5-methyl-2-(1 -methylethyl)-cyclohexyl 2-aminobenzoate, glyceryl aminobenzoate, 2-ethylhexyl-p-dimethylethyl-aminobenzoate, 4- aminobenzamide, homomethyl-N-acetyl-anthranilic acid, menthyl antrhanilate, 2-(1 H-benzimidazol-2-yl)-4-methoxyphenol, 2,2'-bis(benzimidazole), monosodium salt of 2-2'-bis-(1 ,4-phenylene)1 H-benzimidazole-4,6-disulphonic acid, 2-phenylbenzimidazole-5-sulphonic acid, δ.δ'.θ.e'-tetramethyl^^1- bis(benzimidazole), 5,5'-dimethyl-2,2I-bis(benzimidazole), 6-methoxy-2,2'- bis(benzimidazole), 1 ,4-phenylenebis(2-benzimidazolyl), 1 ,2-phenylene- bis)benzimidazolyl), 1 ,4-phenylenebis(N-2-ethylhexyl-2-benzimidazolyl), 1 ,4- phenylenebis(N-tri-methylsilylmethyl-2-benzimidazolyl), 2-(1 H-benzimidazol-2- yl)benzothiazole, 2-(1 H-benzimidazol-2-yl)benzoxazole, N,N'-dimethyl-2,2'- bis(benzimidazole), phenylbenzimidazole-5-sulfonic acid (Ensulizole) and its salts , 2-2l-bis-(1 )4-phenylene)1 H-benzimidazole-4,6-disulphonic acid, 3-me- thylbutyl 4-(dimethylamino)benzoate, 3,3,5-trimethylcyclohexyl 2-hydroxybenzo- ate (Homosalate), ethyl 4-aminobenzoate, 4,4-((6-(((1 ,1-di- methylethyl)amino)carbonyl)phenyl)amino) 1 ,3,5-triazine-2,4-diyl)diimino)bis- ,bis-(2-ethyl-hexyl)ester) benzoic acid, 2,4-dihydroxy-benzophenone (Benzo- phenone-1 ), 2,2'-dihydroxy-4-methoxy-benzophenone (dioxybenzone, Benzo- phenone-8), 2,21-dihydroxy-4,4'-dimethoxy-benzophenone, 2,2I,4,4'-tetrahy- droxy-benzophenone, 2-hydroxy-4-methoxy-4'-nnethyl-benzophenone, hydroxy- methoxy-benzophenone sulfonic acid, (2-Hydroxy-4-methoxyphenyl)-phenyl- methanone (Benzophenone-3), 2-hydroxy-4-methoxy-benzophenone-5-sulfonic acid (Benzophenone-4) and its salts, 4-phenyl-benzophenone, 2-ethylhexyl-4'- phenyl-benzophenone-2-carboxylate, 2-hydroxy-4-n-octoxy-benzophenone, 4- hydroxy-3-carboxy-benzophenone, 4-(2-β-glucopyranosiloxy)-propoxy-2- hydroxybenzophenone, dihydroxy-dimethoxy-disulfobenzophenone, 2- benzothiazol-2-ylphenol, [2,4'-dihydroxy-3-(2H-benzotriazol-2-yl)-5-(1 ,1 ,3,3- tetramethylbutyO^'-n-octoxy-δ'-benzoyll-diphenylmethane, 2,2'-hydroxy-5- methylphenyl-benzotriazole, 2-(2t-hydroxy-5'-t-octylphenyl)benzotriazole, 2-(2'- hydroxy-5'-methylphenyl)benzotriazole, 2,2'-methylene-bis-6-(2H-benzotriazol- 2-yl)-4-(tetramethyl-butyl)-1 ,1 ,3,3-phenol, 2-benzoxazole-2-yl-4-methylphenol, 2-phenyl-5-methylbenzoxazole, 1 ,4-phenylenebis(2-benzoxazolyl), 1 ,3- phenylenebis(2-benzoxazolyl), 1 ,2-phenylenebis(2-benzoxazolyl), 2-(2- benzofuryl)-benzoxazole, 2-(benzofuryl)-5-methylbenzoxazole, 2-(3-methyl-2- benzofuryl)benzoxazole, 3-(4'-methylbenzylidene)-D,L-camphor, terephthalylidene dicamphor sulphonic acid, 3-benzylidene-D,L-camphor, 4- benzylidene-D,L-camphor, di-tert-butyl hydroxybenzylidene camphor, ben- zylidene camphor sulphonic acid, camphor benzalkonium methosulfate, poly- acrylamido-methyl benzylidene camphor, ethylhexyl methoxycinnamate, dietha- nolamine p-methoxy cinnamate, isopropyl-p-acetamido cinnamate, octyl cinna- mate, ethyl-4-isopropylcinnamate, methyl-2,5-diisopropyl cinnamate, ethyl-2,4- diisopropylcinnamate, methyl-2,4-diisopropylcinnamate, propyl-p-methoxycin- namate, isopropyl-p-methoxycinnamate, diisopropylcinnamate esters, isoamyl- p-methoxycinnamate, cyclohexyl-p-methoxycinnamate, ethyl-α-cyano-β-phenyl- cinnamate, 2-ethylhexyl-α-cyano-β-phenylcinnamate, glycerin-mono-2-ethyl- hexanoyl-diparamethoxycinnamate, glyceryl octanoate-di-p-methoxycinnamate, DEA-methoxycinnamate, methyl-bis(trimethyl-siloxy)silyl-isopentyl-trimethoxy- cinnamate, ethyl-α-cyano-3,5-dimethoxy-4-hydroxy cinnamate, ethyl-α-acetyl- 3,5-dimethoxy-4-hydroxy cinnamate, iso-propyl-α-acetyl-3,5-dimethoxy-4-hy- droxy cinnamate, iso-amyl-α-acetyl-3,5-dimethoxy-4-hydroxy cinnamate, 2- ethylhexyl-α-acetyl-3,5-dimethoxy-4-hydroxy cinnamate, ethyl-α-cyano-3-meth- oxy-4-hydroxy cinnamate, ethyl-α-acetyl-3-methoxy-4-hydroxy cinnamate, iso- propyl-α-acetyl-3-methoxy-4-hydroxy cinnamate, iso-amyl-α-acetyl-3-methoxy- 4-hydroxy cinnamate, 2-ethylhexyl-α-acetyl-3-methoxy-4-hydroxy cinnamate, 7- ethylamino-4-methylcoumarin, 7,8-dihydroxycoumarin, 6,7-dihydroxycoumarin, 7-hydroxycoumarin, 4-methyl-7-hydroxycoumarin, diacetycurcumin, tetrahydro- curcumin diacetate, dianisoylmethane, dibenzalazine, butyl methoxydibenzoyl- methane (Avobenzone), 2-methyldibenzoylmethane, 4-methyldibenzoyl- methane, 4-isopropyldibenzoylmethane, 4-tert-butyldibenzoylmethane, 2,4-di- methyldibenzoylmethane, 2,5-dimethyldibenzoylmethane, 4,4'-diisopropyldiben- zoylmethane, 4,4'-dimethoxydibenzoylmethane, 2-methyl-5-isopropyl-4'-meth- oxydibenzoylmethane, 2-methyl-5-tert-butyl-4'-methoxydibenzoylmethane, 2,4- dimethyl-4'-methoxydibenzoylmethane, 2,6-dimethyl-4-tert-butyl-4'-methoxy- dibenzoylmethane, ferulic acid, dimethicodiethylbenzalmalonate, diethyl-3,5-di- methoxy-4-hydroxy benzylidene malonate, di-(2-ethylhexyl)-3,5-dimethoxy-4- hydroxy benzylidene malonate, diisoamyl-3,5-dimethoxy-4-hydroxy benzylidepe malonate, didodecyl-3,5-dimethoxy-4 hydroxy benzylidene malonate, dipalmi- toyl-3,5-dimethoxy-4-hydroxy benzylidene malonate, di-isopropyl-3,5-dimethoxy- 4-hydroxy benzylidene malonate, diethyl-3-methoxy-4-hydroxy benzylidene malonate, di-(2-ethylhexyl)-3-methoxy-4-hydroxy benzylidene malonate, diisoa- myl-3-methoxy-4-hydroxy benzylidene malonate, didodecyl-3-methoxy-4-hy- droxy benzylidene malonate, dipalmitoyl-3-methoxy-4-hydroxy benzylidene malonate, di-isopropyl-3-methoxy-4-hydroxy benzylidene malonate, hydrolyzed aspergillus sp. extract ferment, 4-nitrobenzamide, 4-nitrobenzoic acid, p-amino- benzoic acid (PABA), PABA-monoglycerinester, N,N-dipropoxy-PABA-ethyles- ter, N,N-diethoxy PABA-ethylester, N,N-dimethyl PABA-ethylester, N,N-dimethyl PABA-butylester, PEG-25 PABA, N,N-dimethyl PABA-amylester, N,N-dimethyl PABA-octlylester (2-ethylhexyl 4-(dimethylamino)benzoate, Padimate O), octyl dimethyl PABA, ethyl-dihydroxypropyl-PABA, isoamyl dimethyl PABA (3-methyl- butyl 4-(dimethylamino)benzoate, Padimate A), 1-(3,4-dimethoxyphenyl)-4,4- diemthyl-1 ,3-pentanedione, 5-(3,3-Dimethyl-2-norbornyliden)-3-pentane-2-one, 1-(4-methoxyphenyl)-3-(4-tert-butylphenyl)propane-1 ,3-dione, dipropylene glycol salicylate, 2-ethylhexyl 2-cyano-3,3-diphenyl-2-propenoate (Octocrylene), hy- drolyzed soy extract, hydrolyzed linseed extract, sunflower seed extract, grape seed extract, pinus pinaster bark extract, pinus pinaster bud extract, ginseng extract ferment, spirulina platensis powder, p-tert-butylphenyl salicylate, p- octylphenyl salicylate, 2-ethylhexyl salicylate (octyl salicylate), amyl salicylate, menthyl salicylate, homomenthyl salicylate, benzyl salicylate, p-isopropanol- phenyl salicylate, TEA-salicylate, 2-(2H-benzotriazol-2-yl)-4-methyl-6-[2-methyl- 3-[1 ,3,3,3-tetramethyM -[(trimethylsilyl)oxy]disiloxanyl]propyl]-phenol (Mexoryl XL), 2-[p-(tert-butylamido)anilino]-4,6-bis[p-(2'-ethylhexyl-r- oxycarbonyl)anilino]-1 ,3,5-triazine (INCI name: Diethylhexyl Butamido Triazone), 2,4,6-tris[4-(2-ethylhexyl-oxycarbonyl)-anilino]-1 ,3,5-triazine (INCI name: Ethylhexyl Triazone), (1 ,3,5)-triazine-2,4-bis((4-2-ethyl-hexyloxy)-2- hydroxy)-phenyl)-6-(4-methoxy-phenyl) (bemotrizinol), octyl triazone (CAS-no.: 88122-99-0), urocanic acid, ethyl-urocanic acid, talc, kaolin, calcium carbonate, bisoctrizole (CAS-no.: 103597-45-1), bomelone (CAS-no.: 2226-11-1 ), 2- hydroxy-1 ,4-naphthochinone (Lawsone, CAS-no.: 83-72-7), petrolatum red, phenol sulphonate, sodium 3,4-dimethylphenyl-glyoxylate, 3,3'-(1.4- phenylenedimethylene-bis-(7,7-dimethyl-2-oxobicyclo-[2,2,1]hept-1-yl- methanesufonic acid, α-(2-oxoborn-3-ylidene)-toluene-4-sulphonic acid, 2-(2H- benzotriazole-2-yl)-4-methyl-6-[2-methyl-3-[1 ,3,3,3-tetramethyl-1- [(trimethylsilyl)oxy]disiloxanyl]propyl]-phenol (INCI name: drometrizole trisiloxane, DTS), digalloyl trioleate, dimethicone/PEG-15 crosspolymer, ethylhexyl-bis-isopentyl-benzoxazolyl-phenyl melamine and 2-ethylhexyl- dimethoxy-benzylidene-dioxo-imidazolidine propionate;
and/or at least one of its stereoisomers, preferably enantiomers or diastereomers, a racemate or a mixture of at least two of the stereoisomers, preferably enantiomers and/or diastereomers in any mixing ratio, or at least one physiologically acceptable salt and/or at least one corresponding solvate of the afore mentioned compounds.
18. A light-stabilized composition according to claim 14, characterized in that the light-stabiling component comprises a combination of at least one heptaazaphenalene compound according to claim 13 and at least one compound according to claims 16 and/or 17.
19. A light-stabilized composition according to at least one of claims 1 to 18, characterized in that the polymer is at least one polymer selected from the group comprising thermoplastic polymers, thermosetting polymers, elastomers and/or coordination polymers.
20. A light-stabilized composition according to claim 19, characterized in that the thermoplastic polymer is at least one polymer selected from the group comprising acrylonitrile-butadiene-styrene (ABS) copolymer; cellulose derivatives such as cellulose acetate, cellulose acetate propionate, cellulose acetate butyrate, cellulose triacetate, cellulose ether, methylcellulose, ethylcellulose, propylcellulose, hydroxyethylcellulose, hydroxypropylcellulose, hydroxypropylmethylcellulose and carboxy methylcellulose; ethylene-vinyl acetate (EVA) copolymer; ethylene vinyl alcohol (EVAL) copolymer; polyolefines such as ethylen-propylen copolymer, ethylene-buten-1 copolymer, ethylene- hexene copolymer, ethylene-methylpentene copolymer, ethylene-heptene copolymer, ethylene octene copolymer, polybutylene (PB), polymethylpentene (PMP), polypropylene (PP) and polyethylene (PE) such as low density polyethylene (LDPE), linear low density polyethylene (LLDPE), high density polyethylene (HDPE) and metallocene-PE (mPE); ethylen-alkylacrylate copolymer such as ethylen-ethylacrylate copolymer; ethylene- alkylmethylacrylate copolymer; fluoro resins such as polytetrafluoroethylene (PTFE) or perfluoro (ethylene-propylene) copolymer (FEP); chloro- trifluoroethylene (CTFE), ethylene-chlorotrifluoroethylene (ECTFE); ethylene- tetrafluorethylene copolymer (ETFE) and tetrafluoroethylene-propylene copolymer; ionomer; liquid crystal polymer (LCP); polyacetal; polyacrylate; polymethacrylate; polyacrylonitrile; polyamide (PA); polyamide-imide; polyesters such as polybutylene terephthalate (PBT), polyethylene terephthalate (PET) and polycyclohexylene dimethylene terephthalate (PCT); polycarbonate (PC); polyhydroxyalkanoate; polyketone (PK); polyetheretherketone (PEEK); polyetherimide (PEI); polyethersulfone (PES); polyimide (Pl); polylactic acid (PLA); polyphenylene oxide (PPO); polyphenylene sulfide (PPS); polyphthalamide (PPA); homo- or copolymers of styrene such as e.g. styrene- isopren-styrene block copolymer; polysulfone (PSU); polyurethane (PU); polyvinyl ether; polyvinylalcohol; polyvinylidenechloride; polyvinylpyrrolidone; polyvinyl chloride (PVC); vinyl chloride-vinyl acetate copolymer; vinyl chloride- vinylidene dichloride copolymer and vinyl pyrrolidon-ethylen-vinylacetate copolymer.
21. A light-stabilized composition according to claim 19, characterized in that the thermosetting polymer is at least one polymer selected from the group comprising vulcanized rubber; polyoxybenzylmethylenglycolanhydride; duroplast; urea-formaldehyde resins; melamine; cured polyester resins and epoxy resins.
22. A light-stabilized composition according to claim 19, characterized in that the elastomer is at least one polymer selected from the group comprising homo-, CO- or block polymer of butadiene; natural rubber (NR); polyisoprene (IR); butyl rubber; halogenated butyl rubbers such as chloro butyl rubber or bromo butyl rubber; polybutadiene (BR); styrene-butadiene rubber (SBR); nitrile rubber; hydrated nitrile rubbers (HNBR); chloroprene rubber (CR); polychloroprene; neoprene; ethylene propylene rubber (EPM); ethylene propylene diene rubber (EPDM); epichlorohydrin rubber (ECO); polyacrylic rubber; silicone rubber; silicone; silcone derivatives such as siloxane-methacrylate polymers; fluorosilicone rubber; fluoroelastomers; perfluoroelastomers (FFKM); tetrafluoro ethylene/propylene rubbers (FEPM); chlorosulfonated polyethylene (CSM); ethylene-vinyl acetate (EVA) copolymers; thermoplastic elastomers (TPE); polyurethane rubber and polysulfide rubber.
23. A light-stabilized composition according to anyone of claims 19 to 22, characterized in that the composition comprises at least one further additive selected from the group comprising anti-blocking-agents, anti-fogging agents, antistatic agents, antioxidants, biocides, blowing agents, defoamers, dyes, emulsifiers, fillers, flame retardants, heat stabilizers, impact modifiers, lubricants, metal deactivators, mould-release agents, optical brighteners, plastisizers, processing agents, pigments, phosphites, phosphonites, reinforcing agents, rheology additives, slip agents and surfactants.
24. A light-stabilized composition according to at least one of claims 1 to 23 in form of a painting, a coating, textile fibers or granulate.
25. An article, mould, sheet, foil or film produced of a composition according to any one of claims 1 to 23.
26. Use of at least one heptaazaphenalene compound according to claims 1 to 13 in an amount of 0.01 to 25 % by weight, based on the total weight of the composition, as a light-stabilizing component for polymers.
27. Use of a combination comprising at least one heptaazaphenalene compound according to claims 1 to 13 and at least one further light-stabilizing compound (Z) according to claims 14, 15 or 16 as light-stabilizing component for polymers in an amount of 0.01 to 25 % by weight, based on the total weight of the composition.
28. A light stabilizer combination comprising at least one heptaazaphenalene compound according to claims 1 to 13 and at least one further light stabilizer (Z) of general formulae (L1 ), (L2), (L3), (L4), (L5), (L6), (L7), (L8), (L9), (L10), (L11 ), (L12), (L13) and/or (L14) as defined in claim 15;
and optionally at least one further light stabilizer (Z) of general formula (X) and/or (Is) as defined in claim 15.
29. A light stabilizer combination comprising at least one heptaazaphenalene compound according to claims 1 to 13 and at least one further light stabilizer (Z) according to claim 15; and optionally at least one further light-stabilizer (Z) according to claim 16.
PCT/EP2008/000173 2007-01-12 2008-01-11 Light-stabilized composition WO2008083975A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP07000635 2007-01-12
EP07000635.8 2007-01-12

Publications (1)

Publication Number Publication Date
WO2008083975A1 true WO2008083975A1 (en) 2008-07-17

Family

ID=38110354

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2008/000173 WO2008083975A1 (en) 2007-01-12 2008-01-11 Light-stabilized composition

Country Status (1)

Country Link
WO (1) WO2008083975A1 (en)

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010094378A1 (en) * 2009-02-17 2010-08-26 Merck Patent Gmbh Organic electronic device
WO2010132953A1 (en) * 2009-05-22 2010-11-25 Commonwealth Scientific And Industrial Research Organisation Heptaazaphenalene derivatives and use thereof in organic electroluminescent device
WO2013133359A1 (en) 2012-03-09 2013-09-12 国立大学法人九州大学 Light-emitting material, and organic light-emitting element
CN103740004A (en) * 2014-01-16 2014-04-23 唐山师范学院 Light rare-earth hydrotalcite-curcumin composite heat-stable assistant and preparation method thereof
CN106700391A (en) * 2016-12-02 2017-05-24 长兴天晟能源科技有限公司 Functional master batch for improving weather resistance of ABS (acrylonitrile butadiene styrene copolymers)
CN109081999A (en) * 2018-07-10 2018-12-25 武汉金牛经济发展有限公司 A kind of color masterbatch and preparation method thereof of the low precipitation of uvioresistant
EP3536742A1 (en) 2018-03-09 2019-09-11 Polytex Sportbeläge Produktions-GmbH Artificial turf fiber with uv protection substances
CN110335969A (en) * 2019-07-10 2019-10-15 成都信息工程大学 A kind of light emitting diode and preparation method thereof based on exciplex system
CN110824837A (en) * 2018-08-07 2020-02-21 新应材股份有限公司 Photosensitive resin composition and patterning method using same
CN110982158A (en) * 2019-10-23 2020-04-10 江阴市德惠热收缩包装材料有限公司 Film and method for producing same
US10669412B2 (en) 2016-09-09 2020-06-02 Leoni Kabel Gmbh Elongated article with good flexibility and high flame retardancy
US10920049B2 (en) 2016-09-09 2021-02-16 Leoni Kabel Gmbh Polymer composition with high flexibility and flame retardancy
CN113292282A (en) * 2021-05-22 2021-08-24 杭州富阳捷鑫彩钢有限公司 Method for manufacturing color sand tiles by recycling casting waste sand
US11248111B2 (en) 2016-09-09 2022-02-15 Leoni Kabel Gmbh Conjunction device such as a cable and polymer composition for preparing same
CN114995061A (en) * 2022-08-01 2022-09-02 明士(北京)新材料开发有限公司 Low-water-absorption positive photosensitive resin composition and preparation method and application thereof
US11453764B2 (en) 2016-09-09 2022-09-27 Leoni Kabel Gmbh Strand-shaped elements and polymer composition for preparing same

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1333128A (en) * 1971-07-07 1973-10-10 Vnii Protivopozharnoi Oborony Fire-retardant composition
JPS5941360A (en) * 1982-08-31 1984-03-07 Nissan Chem Ind Ltd Flame-retardant resin composition
RU1775428C (en) * 1990-08-08 1992-11-15 Научно-производственное объединение "Камень и силикаты" Polystyrene composition
EP0994156A1 (en) * 1998-10-14 2000-04-19 Mitsubishi Engineering-Plastics Corporation Resin composition comprising polyamide resin
WO2001021698A1 (en) * 1999-09-21 2001-03-29 Dsm N.V. Flame-retardant mixture
US20020193533A1 (en) * 2001-03-08 2002-12-19 Hiroshi Kamo Resin composition
DE102004047257A1 (en) * 2004-09-29 2006-04-06 Universität Konstanz Phosphorus-containing heptazine derivatives, process for their preparation and their use
WO2007006807A1 (en) * 2005-07-13 2007-01-18 Isdin, S.A. New derivatives of heptaazaphenalene, methods for obtaining them, and their use as protecting agents against uv radiation

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1333128A (en) * 1971-07-07 1973-10-10 Vnii Protivopozharnoi Oborony Fire-retardant composition
JPS5941360A (en) * 1982-08-31 1984-03-07 Nissan Chem Ind Ltd Flame-retardant resin composition
RU1775428C (en) * 1990-08-08 1992-11-15 Научно-производственное объединение "Камень и силикаты" Polystyrene composition
EP0994156A1 (en) * 1998-10-14 2000-04-19 Mitsubishi Engineering-Plastics Corporation Resin composition comprising polyamide resin
WO2001021698A1 (en) * 1999-09-21 2001-03-29 Dsm N.V. Flame-retardant mixture
US20020193533A1 (en) * 2001-03-08 2002-12-19 Hiroshi Kamo Resin composition
DE102004047257A1 (en) * 2004-09-29 2006-04-06 Universität Konstanz Phosphorus-containing heptazine derivatives, process for their preparation and their use
WO2007006807A1 (en) * 2005-07-13 2007-01-18 Isdin, S.A. New derivatives of heptaazaphenalene, methods for obtaining them, and their use as protecting agents against uv radiation

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; 8 January 1994 (1994-01-08), KARADZHYAN, ELMIRA A. ET AL: "Melem in impact-resistant polystyrene compositions", XP002437771, retrieved from STN Database accession no. 1994:9689 *
DATABASE WPI Week 198416, Derwent World Patents Index; AN 1984-097008, XP002471724 *
SCHROEDER H ET AL: "Some reactions of cyameluric chloride", JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY. EASTON, US, vol. 27, 1962, pages 4262 - 4266, XP002401728, ISSN: 0022-3263 *
WILSON ELIZABETH K: "Old molecules, new chemistry", CHEM ENG NEWS; CHEMICAL AND ENGINEERING NEWS MAY 31 2004, vol. 82, no. 22, 31 May 2004 (2004-05-31), pages 34 - 35, XP002471701 *

Cited By (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102317408B (en) * 2009-02-17 2015-03-04 默克专利有限公司 Organic electronic device
WO2010094378A1 (en) * 2009-02-17 2010-08-26 Merck Patent Gmbh Organic electronic device
US9066410B2 (en) 2009-02-17 2015-06-23 Merck Patent Gmbh Organic electronic device
WO2010132953A1 (en) * 2009-05-22 2010-11-25 Commonwealth Scientific And Industrial Research Organisation Heptaazaphenalene derivatives and use thereof in organic electroluminescent device
US9985215B2 (en) 2012-03-09 2018-05-29 Kyulux, Inc. Light-emitting material, and organic light-emitting element
CN104159994A (en) * 2012-03-09 2014-11-19 国立大学法人九州大学 Light-emitting material, and organic light-emitting element
EP2824159A4 (en) * 2012-03-09 2015-12-09 Univ Kyushu Nat Univ Corp Light-emitting material, and organic light-emitting element
WO2013133359A1 (en) 2012-03-09 2013-09-12 国立大学法人九州大学 Light-emitting material, and organic light-emitting element
CN103740004A (en) * 2014-01-16 2014-04-23 唐山师范学院 Light rare-earth hydrotalcite-curcumin composite heat-stable assistant and preparation method thereof
US10669412B2 (en) 2016-09-09 2020-06-02 Leoni Kabel Gmbh Elongated article with good flexibility and high flame retardancy
US11453764B2 (en) 2016-09-09 2022-09-27 Leoni Kabel Gmbh Strand-shaped elements and polymer composition for preparing same
US11248111B2 (en) 2016-09-09 2022-02-15 Leoni Kabel Gmbh Conjunction device such as a cable and polymer composition for preparing same
US10920049B2 (en) 2016-09-09 2021-02-16 Leoni Kabel Gmbh Polymer composition with high flexibility and flame retardancy
CN106700391A (en) * 2016-12-02 2017-05-24 长兴天晟能源科技有限公司 Functional master batch for improving weather resistance of ABS (acrylonitrile butadiene styrene copolymers)
WO2019170365A1 (en) 2018-03-09 2019-09-12 Polytex Sportbeläge Produktions-Gmbh Artificial turf fiber with uv protection substances
EP3536742A1 (en) 2018-03-09 2019-09-11 Polytex Sportbeläge Produktions-GmbH Artificial turf fiber with uv protection substances
EP4234777A2 (en) 2018-03-09 2023-08-30 Polytex Sportbeläge Produktions-GmbH Artificial turf fiber with uv protection substances
CN109081999A (en) * 2018-07-10 2018-12-25 武汉金牛经济发展有限公司 A kind of color masterbatch and preparation method thereof of the low precipitation of uvioresistant
CN110824837A (en) * 2018-08-07 2020-02-21 新应材股份有限公司 Photosensitive resin composition and patterning method using same
CN110335969A (en) * 2019-07-10 2019-10-15 成都信息工程大学 A kind of light emitting diode and preparation method thereof based on exciplex system
CN110335969B (en) * 2019-07-10 2021-07-16 成都信息工程大学 Light-emitting diode based on exciplex system and preparation method thereof
CN110982158A (en) * 2019-10-23 2020-04-10 江阴市德惠热收缩包装材料有限公司 Film and method for producing same
CN113292282A (en) * 2021-05-22 2021-08-24 杭州富阳捷鑫彩钢有限公司 Method for manufacturing color sand tiles by recycling casting waste sand
CN113292282B (en) * 2021-05-22 2022-06-10 杭州富阳捷鑫彩钢有限公司 Method for manufacturing color sand tiles by recycling casting waste sand
CN114995061A (en) * 2022-08-01 2022-09-02 明士(北京)新材料开发有限公司 Low-water-absorption positive photosensitive resin composition and preparation method and application thereof
CN114995061B (en) * 2022-08-01 2022-11-01 明士(北京)新材料开发有限公司 Low-water-absorption positive photosensitive resin composition and preparation method and application thereof

Similar Documents

Publication Publication Date Title
WO2008083975A1 (en) Light-stabilized composition
BE1014298A3 (en) Blends stabilizers.
NL1023157C2 (en) Stabilizer mixtures.
JP4587488B2 (en) A synthetic resin composition containing a low basic hindered amine compound having a carbonate skeleton and a coating composition containing the same.
KR101074723B1 (en) Resin Compositions
US7169835B2 (en) Stabilizer mixture
KR20050005482A (en) β-crystalline polypropylenes
AU2014336388B2 (en) Triazine, piperidine and pyrrolidine based hindered amine light stabilizers
AU2002362127A1 (en) Uv stabilized thermoplastic olefins
NO319839B1 (en) UV stabilizing additive mixture or concentrate and polymeric article protected from UV light
KR19980024774A (en) Hydroxyphenyltriazine
CN1675300A (en) Beta-nucleating, light stabilizing agents for polypropylene
CA3035621A1 (en) Additive mixture
TWI278479B (en) Stabilizer mixtures for the protection of polymer substrates
US9034955B2 (en) High molecular weight nonpolar benzotriazoles
JP2003535206A (en) Stabilizer mixture
US9725578B2 (en) Sterically hindered polymeric amines and their use as polymer stabilizers
RU2605940C2 (en) 5h-furan-2-one derivatives for stabilisation of organic material
KR101330607B1 (en) Color Fast Polyurethanes
US8404765B2 (en) Sterically hindered amines and use thereof as polymer stabilizers
KR101373983B1 (en) Stabilizer compositions for improved protection against degradation of organic substrates by light
FR2783827A1 (en) COMPOUND, COMPOSITION CONTAINING SAME AND USE AS STABILIZER
CA3094725A1 (en) Use of an ultraviolet radiation absorbing composition as a light stabilizer for a shaped artificial polymer article
JP5350013B2 (en) Novel triazine-based compound, process for producing the same, ultraviolet absorber comprising the same, and polymer composition containing the same
FR2576598A1 (en) NOVEL TRIAZOLIC COMPOUNDS, ORGANIC POLYMERS CONTAINING THEM, AND THE APPLICATION OF THESE TRIAZOLIC COMPOUNDS TO THE STABILIZATION OF ORGANIC POLYMERS

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 08701080

Country of ref document: EP

Kind code of ref document: A1

DPE1 Request for preliminary examination filed after expiration of 19th month from priority date (pct application filed from 20040101)
NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 08701080

Country of ref document: EP

Kind code of ref document: A1