Benzotriazoles containing α-cumyl groups substituted by heteroatoms and compositions stabilized therewith

• US 6,451,887 B1
• Filed: 08/03/2000
• Issued: 09/17/2002
• Est. Priority Date: 08/03/2000
• Status: Expired due to Fees

• Current Assignee: Ciba Specialty Chemicals Corp (BASF SE)
• Original Assignee: Ciba Specialty Chemicals Corp (BASF SE)
• Inventors: Hendricks-Guy, Carmen, Wood, Mervin G., Ravichandran, Ramanathan, Lau, Jacqueline, Suhadolnik, Joseph, Bulliard, Christophe
• Primary Examiner(s): SZEKELY, PETER A
• Application Number:
  US09/632,216
• Time in Patent Office: 775 Days
• Field of Search: 548/259, 548/260, 548/261, 524/91, 514/359, 424/59, 568/333
• US Class Current: 524/91
• CPC Class Codes: C07D 249/20 with aryl radicals directly attached in position 2
• CPC Class Codes: C08K 5/3475 condensed with carbocyclic rings

Abstract

2H-Benzotriazole UV absorbers substituted at the 3-position and/or the 5-position of the phenyl ring by α-cumyl moiety which is substituted by a heteroatom are particularly photostable in automotive coatings, and are of low color and exhibit low volatility in thermoplastic compositions.

Claims

1. A compound of formula I, II or III

wherein

G₁ is hydrogen or halogen,

G₂ is hydrogen, cyano, perfluoroalkyl of 1 to 12 carbon atoms, halogen, —

CO—

G₃, —

COOG₃, —

CONHG₃, —

CON(G₃)₂, E₃SO—

, E₃SO₂—

, nitro, —

P(O)(C₆H₅)₂, —

P(O)(OG₃)₂,

G₃ is hydrogen, straight or branched chain alkyl of 1 to 24 carbon atoms, straight or branched chain alkenyl of 2 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, phenyl, or said phenyl or said phenylalkyl substituted on the phenyl ring by 1 to 4 alkyl of 1 to 4 carbon atoms,

E₁ is hydrogen, straight or branched chain alkyl of 1 to 24 carbon atoms, straight or branched chain alkenyl of 2 to 24 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, phenyl, or said phenyl or said phenylalkyl substituted on the phenyl ring by 1 to 4 alkyl of 1 to 4 carbon atoms;

or E₁ is alkyl of 1 to 24 carbon atoms substituted by one or two hydroxy groups;

or E₁ is alkyl of 1 to 24 carbon atoms, alkenyl of 2 to 18 carbon atoms, said alkyl or said alkenyl substituted by one or more —

OCOE₁₁, —

OE₄, —

NCO, —

NHCOE₁₁, or —

NE₇E₈, or mixtures thereof, where E₄ is straight or branched chain alkyl of 1 to 24 carbon atoms or straight or branched chain alkenyl of 2 to 18 carbon atoms;

or said alkyl or said alkenyl interrupted by one or more —

O—

, —

NH—

or —

NE₄—

groups or mixtures thereof and which can be unsubstituted or substituted by one or more —

OH, —

OE₄ or —

NH₂, or mixtures thereof;

or E₁ is a group of formula IV or V

where

E₂₇ and E₂₈ are independently alkyl of 1 to 18 carbon atoms, or cycloalkyl of 5 to 12 carbon atoms;

E₂₂, E₂₃, E₂₄, E₂₅ and E₂₆ are independently hydrogen, halogen, straight or branched alkyl of 1 to 18 carbon atoms, alkenyl of 2 to 18 carbon atoms, said alkyl or said alkenyl substituted by one or more halogen, —

OCOE₁₁, —

OE₄, —

NCO, —

NHCOE₁₁, or —

NE₇E₈, or mixtures thereof, where E₄ is straight or branched chain alkyl of 1 to 24 carbon atoms or straight or branched chain alkenyl of 2 to 18 carbon atoms;

or said alkyl or said alkenyl interrupted by one or more —

O—

, —

NH—

or —

NE₄—

groups or mixtures thereof and which can be unsubstituted or substituted by one or more —

OH, —

OE₄ or —

NH₂, or mixtures thereof;

or

E₂₂, E₂₃, E₂₄, E₂₅ and E₂₆ are independently phenyl, —

OH, —

OCOE₁₁, —

OE₂₉, —

NCO, —

NHCOE₁₁ or —

NE₇E₈, cyano, nitro, perfluoroalkyl of 1 to 12 carbon atoms, —

COG₃, —

COOG₃, —

CON(G₃)₂, —

CONHG₃, E₃S—

, E₃SO—

, E₃SO₂—

, —

P(O)(C₆H₅)₂, —

P(O))OG₃)₂, —

SO₂—

X₁—

E₂₉;

X₁ is —

O—

, —

NH—

or —

NE₄—

;

E₂₉ is straight or branched chain alkyl of 1 to 24 carbon atoms, straight or branched chain alkenyl of 2 to 18 carbon atoms, said alkyl or said alkenyl substituted by one or more —

OH, —

OCOE₁₁, —

OE₄, —

NCO, —

NHCOE₁₁, —

NE₇E₈, phthalimido,

or mixtures thereof, where E₄ is straight or branched chain alkyl of 1 to 24 carbon atoms or alkenyl of 2 to 18 carbon atoms;

or said alkyl or said alkenyl interrupted by one or more —

O—

, —

NH—

or —

NE₄—

groups or mixtures thereof and which can be unsubstituted or substituted by one or more —

OH, —

OE₄ or —

NH₂, or mixtures thereof;

or E₂₉ is phenyl or phenylalkyl of 7 to 15 carbon atoms, or said phenyl or said phenylalkyl substituted by one to three alkyl groups of 1 to 4 carbon atoms;

E₂ is straight or branched alkyl chain of 1 to 24 carbon atoms, straight or branched chain alkenyl of 2 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, phenyl, or said phenyl or said phenylalkyl substituted on the phenyl ring by one to three alkyl of 1 to 4 carbon atoms;

or E₂ is alkyl of 1 to 24 carbon atoms or said alkenyl of 2 to 18 carbon atoms substituted by one or more —

OH, —

OCOE₁₁, —

OE₄, —

NCO, —

NHCOE₁₁ or —

NE₇E₈, or mixtures thereof, where E₄ is straight or branched chain alkyl of 1 to 24 carbon atoms or alkenyl of 2 to 18 carbon atoms;

or said alkyl or said alkenyl interrupted by one or more —

O—

, —

NH—

or —

NE₄—

groups or mixtures thereof and which can be unsubstituted or substituted by one or more —

OH, —

OE₄ or —

NH₂ groups or mixtures thereof, or E₂ is a group of formula IV or formula V as described above;

n is 1 or 2,

when n is 1, E₅ is OE₆ or NE₇E₈, or

E₅ is —

PO(OE₁₂)₂, —

OSi(E₁₁)₃ or —

OCO—

E₁₁, or straight or branched chain C₁-C₂₄alkyl which is interrupted by —

O—

, —

S—

or —

NE₁₁ and which can be unsubstituted or substituted by —

OH or —

OCO—

E₁₁, C₅-C₁₂ cycloalkyl which is unsubstituted or substituted by —

OH, straight chain or branched C₂-C₁₈alkenyl which is unsubstituted or substituted by —

OH, C₇-C₁₅aralkyl, —

CH₂—

CHOH—

E₁₃ or glycidyl,

E₆ is hydrogen, straight or branched chain C₁-C₂₄alkyl which is unsubstituted or substituted by one or more OH, OE₄ or NH₂ groups, or —

OE₆ is —

(OCH₂CH₂)_wOH or —

(OCH₂CH₂)_wOE₂₁ where w is 1 to 12 and E₂₁ is alkyl of 1 to 12 carbon atoms,

E₇ and E₈ are independently hydrogen, alkyl of 1 to 18 carbon atoms, straight or branched chain C₃-C₁₈alkyl which is interrupted by —

O—

, —

S—

or —

NE₁₁—

, straight or branched chain alkenyl of 2 to 18 carbon atoms, C₅-C₁₂cycloalkyl, C₆-C₁₄aryl or C₁-C₃hydroxylalkyl, or E₇ and E₈ together with the N atom are a pyrrolidine, piperidine, piperazine or morpholine ring, or

E₅ is —

X—

(Z)_p—

Y—

E₁₅

wherein

X is —

O—

or —

N(E₁₆)—

,

Y is —

O—

or —

N(E₁₇)—

,

Z is C₂-C₁₂-alkylene, C₄-C₁₂-alkylene interrupted by one to three nitrogen atoms, oxygen atoms or a mixture thereof, or is C₃-C₁₂-alkylene, butenylene, butynylene, cyclohexylene or phenylene, each substituted by a hydroxyl group,

m is zero, 1 or 2,

p is 1, or p is also zero when X and Y are —

N(E₁₆)— and

—

N(E₁₇)—

, respectively,

E₁₅ is a group —

CO—

C(E₁₈)═

C(H)E₁₉ or, when Y is —

N(E₁₇)—

, forms together with E₁₇ a group —

CO—

CH═

CH—

CO—

, wherein E₁₈ is hydrogen or methyl, and E₁₉ is hydrogen, methyl or —

CO—

X—

E₂₀, wherein E₂₀ is hydrogen, C₁-C₁₂-alkyl or a group of the formula;

wherein the symbols E₁, G₂, X, Z, m and p have the meanings defined above, and E₁₆ and E₁₇ independently of one another are hydrogen, C₁-C₁₂-alkyl, C₃-C₁₂-alkyl interrupted by 1 to 3 oxygen atoms, or is cyclohexyl or C₇-C₁₅aralkyl, and E₁₆ together with E₁₇ in the case where Z is ethylene, also forms ethylene,

when n is 2, E₅ is one of divalent radicals —

O—

E₉—

O—

or —

N(E₁₁)—

E₁₀—

N(E₁₁)—

,

E₉ is C₂-C₈alkylene, C₄-C₈alkenylene, C₄alkynylene, cyclohexylene, straight or branched chain C₄-C₁₀alkylene which is interrupted by —

O—

or by —

CH₂—

CHOH—

CH₂—

O—

E₁₄—

O—

CH₂—

CHOH—

CH₂—

,

E₁₀ being straight or branched chain C₂-C₁₂alkylene which may be interrupted by —

O—

, cyclohexylene, or

E₁₀ and E₁₁ with the two nitrogen atoms form a piperazine ring,

E₁₄ is straight or branched chain C₂-C₈alkylene, straight or branched chain C₄-C₁₀alkylene which is interrupted by —

O—

, cycloalkylene, arylene or

E₁₁ is hydrogen, straight or branched chain C₁-C₁₈alkyl, C₅-C₁₂cycloalkyl, straight or branched chain C₂-C₁₈alkenyl, C₆-C₁₄ aryl or C₇-C₁₅aralkyl,

E₁₂ is straight or branched chain C₁-C₁₈alkyl, straight or branched chain C₃-C₁₈alkenyl, C₅-C₁₀cycloalkyl, C₆-C₁₆aryl or C₇-C₁₅aralkyl,

E₁₃ is hydrogen, straight chain or branched C₁-C₁₈alkyl which is substituted by —

PO(OE₁₂)₂, phenyl which is unsubstituted or substituted by OH, C₇-C₁₅aralkyl or —

CH₂OE₁₂,

E₁₃ is alkyl of 1 to 20 carbon atoms, hydroxyalkyl of 2 to 20 carbon atoms, alkenyl of 3 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, aryl of 6 to 10 carbon atoms or said aryl substituted by one or two alkyl of 1 to 4 carbon atoms or 1,1,2,2-tetrahydroperfluoroalkyl where the perfluoroalkyl moiety is of 6 to 16 carbon atoms,

T is —

SO—

, —

SO₂—

, —

SO—

E—

SO—

, —

SO₂—

E—

SO₂—

, —

CO—

, —

CO—

CO—

, —

CO—

CH₂—

CO—

, —

CO—

E—

CO—

, —

COO—

E—

OCO—

or —

CO—

NG₅—

E—

NG₅—

CO—

,

where E is alkylene of 2 to 12 carbon atoms, cycloalkylene of 5 to 12 carbon atoms, or alkylene interrupted or terminated by cyclohexylene of 8 to 12 carbon atoms;

G₅ is G₃ or hydrogen, and

with the proviso that at least one of E₁ and E₂ must contain a group of formula IV where E₂₂ to E₂₆ are not each hydrogen;

where if

1 to 4 of E₂₂ to E₂₆ hydrogen, the remaining E₂₂ to E₂₆ groups are not each alkyl of 1 to 4 carbon atoms; and

where if 4 of E₂₂ to E₂₆ are each hydrogen, the remaining E₂₂ to E₂₆ group is not halogen.

2. A compound of formula I according to claim 1:

wherein

G₁ is hydrogen,

G₂ is hydrogen, cyano, CF₃—

, fluoro, chloro, —

CO—

G₃, —

COOG₃ or E₃SO₂—

,

G₃ is hydrogen, straight or branched chain alkyl of 1 to 24 carbon atoms, straight or branched chain alkenyl of 2 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, phenyl, or said phenyl or said phenylalkyl substituted on the phenyl ring by 1 to 4 alkyl of 1 to 4 carbon atoms,

E₁ is a group of formula IV or formula V wherein E₂₂-E₂₆ are independently hydrogen, alkyl of 1 to 12 carbon atoms, straight or branched chain alkenyl of 2 to 18 carbon atoms, OH, cyano, —

OE₂₉, chloro, fluoro, —

OCOE₁₁, CF₃, —

COOG₃, E₃S—

, E₃SO₂—

or —

SO₂—

NH—

E₂₉;

E₂₇ and E₂₈ are methyl;

E₂ is straight or branched alkyl chain of 1 to 24 carbon atoms, straight or branched chain alkenyl of 2 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, phenyl, or said phenyl or said phenylalkyl substituted on the phenyl ring by 1 to 3 alkyl of 1 to 4 carbon atoms;

or E₂ is said alkyl of 1 to 24 carbon atoms or straight or branched alkenyl of 2 to 18 carbon atoms;

or said alkyl or said alkenyl substituted by one or more —

OH, —

OCOE₁₁, —

OE₄, —

NCO, —

NHCOE₁₁ or —

NE₇E₈, or mixtures thereof, where E₄ is straight or branched chain alkyl of 1 to 24 carbon atoms or straight or branched chain alkenyl of 2 to 18 carbon atoms;

or said alkyl or said alkenyl interrupted by one or more —

O—

, —

NH—

or —

NE₄—

groups or mixtures thereof and which can be unsubstituted or substituted by one or more —

OH, —

OE₄ or —

NH₂ groups or mixtures thereof;

or E₂ is a group of formula IV or formula V wherein E₂₂-E₂₆ are independently hydrogen, alkyl of 1 to 12 carbon atoms, straight or branched chain alkenyl of 2 to 18 carbon atoms, OH, cyano, —

OE₂₉, chloro, fluoro, —

OCOE₁₁, CF₃, —

COOG₃, E₃S—

, E₃SO₂—

or —

SO₂—

NH—

E₂₉;

E₃ is alkyl of 1 to 20 carbon atoms, hydroxyalkyl of 2 to 20 carbon atoms, alkenyl of 3 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, aryl of 6 to 10 carbon atoms or said aryl substituted by one or two alkyl of 1 to 4 carbon atoms or 1,1,2,2-tetrahydroperfluoroalkyl where the perfluoroalkyl moiety is of 6 to 16 carbon atoms; and

where E₁₁ and E₂₉ are as defined above.

3. A compound of formula I according to claim 1 which is

a. 5-trifluoromethyl-2-[2-hydroxy-3-(4-methoxy-α

-cumyl)-5-tert-butylphenyl]-2H-benzotriazole;

b. 5-trifluoromethyl-2-[2-hydroxy-3-(4-fluoro-α

-cumyl)-5-tert-octylphenyl]-2H-benzotriazole;

c. 2-[2-hydroxy-3-(4-methoxy-α

-cumyl)-5-tert-butylphenyl]-2H-benzotriazole;

d. 2-[2-hydroxy-3-(4-chloro-α

-cumyl)-5-tert-butylphenyl]-2H-benzotriazole;

e. 5-chloro-2-[2-hydroxy-3-(4-chloro-α

-cumyl)-5-tert-butylphenyl]-2H-benzotriazole;

f. 5-chloro-2-[2-hydroxy-3,5-di-(4-chloro-α

-cumyl)phenyl]-2H-benzotriazole;

g. 5-chloro-2-[2-hydroxy-3,5-di-(4-methoxy-α

-cumyl)phenyl]-2H-benzotriazole;

h. 5-trifluoromethyl-2-[2-hydroxy-3-(4-chloro-α

-cumyl)-5-tert-butylphenyl]-2H-benzotriazole;

i. 5-chloro-2-[2-hydroxy-3-(4-methoxy-α

-cumyl)-5-tert-butylphenyl]-2H-benzotriazole;

j. 2-{2-hydroxy-3-[4-(2-dimethylaminoethyl)aminosulfonyl-α

-cumyl]-5-tert-octylphenyl}-2H-benzotriazole;

k. 2-{2-hydroxy-3-[4-(3-dimethylaminopropyl)aminosulfonyl-α

-cumyl]-5-tert-octylphenyl}-2H-benzotriazole;

l. 5-carboxy-2-[2-hydroxy-3-(4-chloro-α

-cumyl)-5-tert-butylphenyl]-2H-benzotriazole;

m. 5-methoxycarbonyl-2-[2-hydroxy-3-(4-chloro-α

-cumyl)-5-tert-butylphenyl]-2H-benzotriazole;

n. 2-{2-hydroxy-3-[4-(2-hydroxyethoxy)-α

-cumyl]-5-tert-butylphenyl}-2H-benzotriazole;

o. 2-{2-hydroxy-3-[4-(2-phthalimidoethoxy)-α

-cumyl]-5-tert-butylphenyl}-2H-benzotriazole;

p. 5-trifluoromethyl-2-[2-hydroxy-3-(3-isopropenyl-α

-cumyl)-5-tert-octylphenyl]-2H-benzotriazole;

q. 5-trifluoromethyl-2-{2-hydroxy-3-[3-(2-hydroxy-1-methylethyl)-α

-cumyl]-5-tert-octylphenyl)-2H-benzotriazole;

r. 5-trifluoromethyl-2-{2-hydroxy-3-[3-(2-methacryloyloxy-1-methylethyl)-α

-cumyl]-5-tert-octylphenyl}-2H-benzotriazole;

s. 5-chloro-2-[2-hydroxy-3-(4-carboxy-α

-cumyl)-5-methylphenyl]-2H-benzotriazole;

t. 5-chloro-2-[2-hydroxy-3-(4-octadecyloxycarbonyl-α

-cumyl)-5-methylphenyl]-2H-benzotriazole;

or

u. 2-[2-hydroxy-3-(4-octadecylaminosulfonyl-α

-cumyl)-5-tert-octylphenyl]-2H-benzotriazole.

4. A stabilized composition which comprises

(a) an organic material subject to degradation by heat, light or oxygen, and

(b) an effective stabilizing amount of a compound of formula I, II or III according to claim 1.

5. A composition according to claim 4 wherein component (a) is a thermoplastic polyolefin, polyester, polyester urethane, polyether urethane or a water-borne coating.

6. A composition according to claim 5 wherein component (a) is selected from the group consisting of polypropylene, thermoplastic polyolefin, low density polyethylene, medium density polyethylene, high density polyethylene, linear low density polyethylene, poly(butene-1), ethylene/vinyl acetate copolymer, ethylene/propylene copolymer, copolymers of ethylene or propylene with other alpha-olefins, copolymers of acrylonitrile-butadiene-styrene (ABS), copolymers of acrylonitrile and styrene that are impact modified with ethylene-propylene rubber or ethylene/propylene/alpha-olefin rubber or butyl acrylate rubber, blends of ABS and polycarbonate, blends of ABS and poly(vinyl chloride) (PVC), poly(vinyl chloride), copolymers of styrene and butadiene (HIPS), copolymers of styrene and butadiene that also contain ethylene-propylene rubber or ethylene/propylene/alpha-olefin rubber or butyl acrylate rubber, thermoplastic elastomers and thermoplastic vulcanizates.

7. A composition according to claim 5 wherein component (a) is a polyester or polyether urethane or water-borne coating.

8. A composition according to claim 6 which additionally contains an effective stabilizing amount of at least one coadditive stabilizer selected from the group consisting of the phenolic antioxidants, metal stearates, metal oxides, organophosphorus compounds, furanone antioxidants, hydroxylamines, UV absorbers, non-NOR hindered amines, NOR hindered amines and mixtures thereof.

9. A composition according to claim 6 which additionally contains a filler.

10. A composition according to claim 9 wherein the filler is calcium carbonate, clay, talc, mica or glass.

11. A composition according to claim 6 wherein component (a) is a polyolefin film, fiber or thick section, ABS, high impact polystyrene (HIPS), thermoplastic polyolefin, thermoplastic elastomer or thermoplastic vulcanizate which additionally contains a halogenated flame retardant.

12. A composition according to claim 11 wherein the flame retardant is tris[3-bromo-2,2-bis(bromomethyl)propyl]phosphate, decabromodiphenyl oxide, ethylene bis(tetrabromophthalimide) or ethylene bis(dibromonorbornanedicarboximide).

13. A composition according to claim 6 wherein component (a) is polypropylene fiber.

14. A composition according to claim 6 wherein component (a) is polypropylene, polyethylene or thermoplastic polyolefin (TPO).

15. A composition according to claim 14 wherein component (a) is a paintable thermoplastic olefin (TPO).

16. A composition according to claim 4 which additionally comprises a coadditive stabilizer which is a hindered phenolic antioxidant selected from the group consisting of neopentanetetrayl tetrakis(3,5-di-tert-butyl-4-hydroxyhydrocinnamate, octadecyl 3,5-di-tert-butyl-4-hydroxyhydrocinnamate, 1,3,5-trimethyl-2,4,6-tris(3,5,-di-tert-butyl-4-hydroxybenzyl)benzene, 1,2-bis(3,5-di-tert-butyl-4-hydroxyhydrocinnamoyl)hydrazine, calcium [bis(monoethyl 3,5-ditert-butyl-4-hydroxybenzyl)phosphonate], 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)isocyanurate and 1,3,5-tris(3-hydroxy-4-tert-butyl-2,6-dimethylbenzyl)isocyanurate;

or is an organophosphorus stabilizer selected from the group consisting of tris(2,4-di-tert-butylphenyl)phosphite, bis(2,4-di-tert-butyl-6-methylphenyl)ethyl phosphite, 2,2′

,2″

-nitrile[triethyl-tris-(3,3′

,5,5′

-tetra-tert-butyl-1,1′

-biphenyl-2,2′

-diyl)phosphite], tetrakis(2,4-di-butylphenyl) 4,4′

-biphenylenediphosphonite, tris(nonylphenyl)phosphite, bis(2,4-di-tert-butylphenyl)pentaerythritol diphosphite, 2,2′

-ethylidenebis(2,4-di-tert-butylphenyl)fluorophosphite and 2-butyl-2-ethylpropan-1,3-diyl 2,4,6-tri-tert-butylphenyl phosphite;

or is 5,7-di-tert-butyl-3-(3,4-dimethylphenyl)-2H-benzofuran-2-one;

or is N,N-dialkylhydroxylamine made by the direct oxidation of N,N-di(hydrogenated tallow)amine;

or is a hindered amine selected from the group consisting of bis(2,2,6,6-tetramethylpiperidin-4-yl)sebacate, the polycondensation product of 1-(2-hydroxyethyl)-2,2,6,6-tetramethyl-4-hydroxypiperidine and succinic acid, N,N′

,N″

,N″

′

-tetrakis[4,6-bis(butyl-1,2,2,6,6-pentamethylpiperidin-4-yl)amino-s-triazin-2-yl]-1,10-diamino-4,7-diazadecane, the polycondensation product of 4,4′

-hexamethylenebis(amino-2,2,6,6-tetramethylpiperidine) and 2,4-dichloro-6-tert-octylamino-s-triazine, the polycondensation product of 4,4′

-hexamethylenebis(amino-2,2,6,6-tetramethylpiperidine) and 2,4-dichloro-6-morpholino-s-triazine, the polycondensation product of 4,4′

-hexamethylenebis(amino-1,2,2,6,6-pentamethylpiperidine) and 2,4-dichloro-6-morpholino-s-triazine, 2,2,6,6-tetramethylpiperidin-4-yl octadecanoate, 3-dodecyl-1-(1-acetyl-2,2,6,6-tetramethylpiperidin-4-yl)-pyrrolidin-2,5-dione, 1,3,5-tris{N-cyclohexyl-N-[2-(2,2,6,6-tetramethylpiperazin-3-on-4-yl)ethyl]amino}-s-triazine, poly[methyl 3-(2,2,6,6-tetramethylpiperidin-4-yloxy)propyl]siloxane, the polycondensation product of 2,4-dichloro-6-(2,2,6,6-tetramethylpiperidin-4-yl)butylamino)-s-triazine, 2,2′

ethylene-bis{[2,4-(2,2,6,6-tetramethylpiperidin-4-yl)butylamino-s-triazin-6-yl]aminotrimethyleneamino}, oligomer of N-{[2-(N-2,2,6,6-tetramethylpiperidin-4-yl)butylamino]-s-triazin-4-yl}-N,N′

-bis(2,2,6,6-tetramethylpiperidin-4-yl)-1,6-hexanediamine terminated with 2,4-bis(dibutylamino)-s-triazin-6-yl, N,N′

,N″

-tris{2,4-bis[N-(1,2,2,6,6-pentamethylpiperidin-4-yl)butylamino]-s-triazin-6-yl}-3,3′

-ethylenediiminodipropylamine, N,N′

,N″

′

-tris (2,4-bis[N-(1,2,2,6,6-pentamethylpiperidin-4-yl)butylamino]-s-triazin-6-yl}-3,3′

-ethylenediiminodipropylamine and N,N′

,N″

,N′

″

-tetrakis{2,4-bis[N-(1,2,2,6,6-pentamethylpiperidin-4-yl)butylamino]-s-triazin-6-yl}-3,3′

-ethylenediiminodipropylamine;

or is another N-hydrocarbyloxy substituted hindered amines selected from the group consisting of bis(1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl)sebacate, bis(1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl)adipate, bis(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)adipate, bis(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)sebacate, 1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl octadecanoate, N,N′

,N″

-tris{2,4-bis[N-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)butylamino]-s-triazin-6-yl}-3,3′

-ethylenediiminodipropylamine, N,N′

,N″

′

-tris{2,4-bis[N-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)butylamino]-s-triazin-6-yl}-3,3′

-ethylenediiminodipropylamine and N,N′

,N″

,N′

″

-tetrakis{2,4-bis[N-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)butylamino]-s-triazin-6-yl}-3,3′

-ethylenediiminodipropylamine;

or a hydroxy substituted N-hydrocarbyloxy substituted hindered amine selected from the group consisting of bis[1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-yl)]sebacate;

a mixture of bis[1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-yl]glutarate and bis[1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-yl]adipate;

1-(2-hydroxy-2-methylpropoxy)-4-octadecanoyloxy-2,2,6,6-tetramethylpiperidine;

bis[1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-yl]adipate;

bis[1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-yl]glutarate;

bis[1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-yl]succinate;

a mixture of bis[1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-yl]glutarate and bis[1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-yl]succinate;

1-(4-octadecanoyloxy-2,2,6,6-tetramethylpiperidin-1-yloxy)-2-octadecanoyloxy-2-methylpropane;

1-(2-hydroxy-2-methylpropoxy)-4-[9-(methoxy-carbonyl)nonanoyloxy]-2,2,6,6-tetramethylpiperidine;

1-(2-hydroxy-2-methylpropoxy)-4-[5-(methoxy-carbonyl)pentanoyloxy]-2,2,6,6-tetramethylpiperidine;

1-(2-hydroxy-2-methylpropoxy)-4-[3-(methoxy-carbonyl)propionyloxy]-2,2,6,6-tetramethylpiperidine;

1-(2-hydroxy-2-methylpropoxy)-4-[4-(methoxy-carbonyl)butyryloxy]-2,2,6,6-tetramethylpiperidine;

or is a UV absorber selected from the group consisting of 2-(2-hydroxy-3,5-di-α

-cumylphenyl)-2H-benzotriazole, 2-(2-hydroxy-5-methylphenyl)-2H-benzotriazole, 5-chloro-2-(2-hydroxy-3,5-di-tert-butylphenyl)-2H-benzotriazole, 2-(2-hydroxy-3,5-di-tert-amylphenyl)-2H-benzotriazole, 2-(2-hydroxy-3-α

-cumyl-5-tert-octylphenyl)-2H-benzotriazole, 2,4-di-tert-butylphenyl 3,5-di-tert-butyl4-hydroxybenzoate, 2-hydroxy-4-n-octyloxybenzophenone, 2,4-bis(2,4-dimethylphenyl)-6-(2-hydroxy-4-octyloxyphenyl)-s-triazine, oligomer of N-{2-[(1-propoxy-2,2,6,6-tetramethylpiperidin-4-yl)butylamino]-s-triazin-4-yl}-N,N′

-bis(1-propoxy-2,2,6,6-tetramethylpiperidin-4-yl)-1,6-hexanediamine terminated with 2,4-bis(dibutylamino)-s-triazin-6-yl, the condensation product of 2-morpholino-4,6-dichloro-s-triazine with N,N′

-bis(1,2,2,6,6-pentamethylpiperidin-4-yl)-1,6-hexanediamine;

or mixtures thereof.

17. A composition according to claim 16 wherein the coadditive stabilizer is neopentanetetrayl tetrakis(3,5-di-tert-butyl-4-hydroxyhydrocinnamate, tris(2,4-di-tert-butylphenyl)phosphite, N,N-dialkylhydroxylamine made by the direct oxidation of N,N-di(hydrogenated tallow)amine, N,N′

,N″

,N″

′

-tetrakis[4,6-bis(butyl-1,2,2,6,6-pentamethylpiperidin-4-yl)amino-s-triazin-2-yl]-1,10-diamino-4,7-diazadecane, the polycondensation product of 4,4′

-hexamethylenebis(amino-2,2,6,6-tetramethylpiperidine) and 2,4-dichloro-6-tert-octylamino-s-triazine, the polycondensation product of 4,4′

-hexamethylenebis(amino-2,2,6,6-tetramethylpiperidine) and 2,4-dichloro-6-morpholino-s-triazine, the polycondensation product of 4,4′

-hexamethylenebis(amino-1,2,2,6,6-pentamethylpiperidine) and 2,4-dichloro-6-morpholino-s-triazine, oligomer of N-{[2-(N-2,2,6,6-tetramethylpiperidin-4-yl)butylamino]-s-triazin-4-yl}-N,N′

-bis(2,2,6,6-tetramethylpiperidin-4-yl)-1,6-hexanediamine terminated with 2,4-bis(dibutylamino)-s-triazin-6-yl, N,N′

,N″

-tris(2,4-bis[N-(1,2,2,6,6-pentamethylpiperidin-4-yl)butylamino]-s-triazin-6-yl}-3,3′

-ethylenediiminodipropylamine, N,N′

,N″

′

-tris(2,4-bis[N-(1,2,2,6,6-pentamethylpiperidin-4-yl)butylamino]-s-triazin-6-yl}-3,3′

-ethylenediiminodipropylamine and N,N′

,N″

,N′

″

-tetrakis{2,4-bis[N-(1,2,2,6,6-pentamethylpiperidin-4-yl)butylamino]-s-triazin-6-yl}-3,3′

-ethylenediiminodipropylamine, oligomer of N-{2-[(1-propoxy-2,2,6,6-tetramethylpiperidin-4-yl)butylamino]-s-triazin-4-yl}-N,N′

-bis(1-propoxy-2,2,6,6-tetramethylpiperidin-4-yl)-1,6-hexanediamine terminated with 2,4-bis(dibutylamino)-s-triazin-6-yl, or the condensation product of 2-morpholino-4,6-dichloro-s-triazine with N,N′

-bis(1,2,2,6,6-pentamethylpiperidin-4-yl)-1,6-hexanediamine.

18. A composition according to claim 4 which additionally contains another UV absorber selected from the group consisting of the benzotriazoles, the s-triazines, the oxanilides, the salicylates, the hydroxybenzophenones, the benzoates and the α

-cyanoacrylates.

19. A composition according to claim 4 which additionally contains a UV absorber selected from the group consisting of

(a) 5-trifluoromethyl-2-(2-hydroxy-3-α

-cumyl-5-tert-octylphenyl)-2H-benzotriazole;

(b) 5-trifluoromethyl-2-(2-hydroxy-5-tert-octylphenyl)-2H-benzotriazole;

(c) 5-trifluoromethyl-2-(2-hydroxy-3,5-di-tert-octylphenyl)-2H-benzotriazole;

(d) 2,2′

-methylene-bis[6-(5-trifluoromethyl-2H-benzotriazol-2-yl)-4-tert-octylphenol];

(e) methylene-2-[4-tert-octyl-6-(2H-benzotriazol-2-yl)phenol]2′

-[4-tert-octyl-6-(5-trifluoromethyl-2H-benzotriazol-2-yl)phenol];

(f) 3-(5-trifluoromethyl-2H-benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinnamic acid;

(g) methyl 3-(5-trifluoromethyl-2H-benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinnamate;

(h) isooctyl 3-(5-trifluoromethyl-2H-benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinnamate;

(i) 5-trifluoromethyl-2-[2-hydroxy-5-(3-hydroxypropyl)phenyl]-2H-benzotriazole;

(j) 5-trifluoromethyl-2-[2-hydroxy-5-(3-acryloyloxypropyl)phenyl]-2H-benzotriazole;

(k) 5-trifluoromethyl-2-[2-hydroxy-5-(3-methacryloyloxypropyl)phenyl]-2H-benzotriazole;

(l) 5-trifluoromethyl-2-[2-hydroxy-5-(3-acrylylaminopropyl)phenyl]-2H-benzotriazole;

(m) 5-trifluoromethyl-2-[2-hydroxy-5-(3-methacrylylaminopropyl)phenyl]-2H-benzotriazole;

(n) 5-trifluoromethyl-2-(2-hydroxy-3-α

-cumyl-5-tert-butylphenyl)-2H-benzotriazole;

(o) 5-trifluoromethyl-2-(2-hydroxy-3-α

-cumyl-5-nonylphenyl)-2H-benzotriazole;

(p) 5-trifluoromethyl-2-[2-hydroxy-3-α

-cumyl-5-(2-hydroxyethyl)phenyl]-2H-benzotriazole;

(q) 5-trifluoromethyl-2-[2-hydroxy-3-α

-cumyl-5-(3-hydroxypropyl)phenyl]-2H-benzotriazole;

(r) 5-trifluoromethyl-2-(2-hydroxy-3,5-di-tert-amylphenyl)-2H-benzotriazole;

(s) 5-trifluoromethyl-2-(2-hydroxy-3,5-di-tert-butylphenyl)-2H-benzotriazole;

(t) 5-trifluoromethyl-2-(2-hydroxy-3-dodecyl-5-methylphenyl)-2H-benzotriazole;

(u) 5-trifluoromethyl-2-[2-hydroxy-3-tert-butyl-5-(3-hydroxypropyl)phenyl)-2H-benzotriazole;

(v) 5-trifluoromethyl-2-[2-hydroxy-3-tert-butyl-5-(2-hydroxyethyl)phenyl]-2H-benzotriazole;

(w) 5-trifluoromethyl-2-[2-hydroxy-5-(2-hydroxyethyl)phenyl]-2H-benzotriazole;

(x) 5-trifluoromethyl-2-(2-hydroxy-3,5-di-α

-cumylphenyl)-2H-benzotriazole;

(y) 5-fluoro-2-(2-hydroxy-3,5-di-α

-cumylphenyl)-2H-benzotriazole;

(z) 5-butylsulfonyl-2-(2-hydroxy-3,5-di-α

-cumylphenyl)-2H-benzotriazole;

(aa) 5-butylsulfonyl-2-(2-hydroxy-3,5-di-tert-butylphenyl)-2H-benzotriazole;

(bb) 5-butylsulfonyl-2-(2-hydroxy-3,5-di-tert-octylphenyl)-2H-benzotriazole; and

(cc) 5-phenylsulfonyl-2-(2-hydroxy-3,5-di-tert-butylphenyl)-2H-benzotriazole.

20. A composition according to claim 4 which is a stabilized stoving lacquer wherein component (a) is an acid catalyzed resin based on hot crosslinkable, acrylic, acrylic melamine, polyester, polyurethane, polyamide or alkyd resin.

21. A composition according to claim 20 which additionally contains another UV absorber selected from the group consisting of the benzotriazoles, the s-triazines, the oxanilides, the salicylates, the hydroxybenzophenones, the benzoates and the α

-cyanoacrylates.

22. A composition according to claim 20 which is an enamel of high solids content for industrial finishes.

23. A composition according to claim 22 which is a finishing enamel for automobiles.

24. A composition according to claim 4 which is a stabilized ambient curable composition wherein component (a) is a resin selected from the group consisting of unmodified or modified alkyd resin, acrylic resin, acrylic alkyd resin, polyester resin or crosslinkable epoxide resin.

25. A composition according to claim 24 wherein the resin is selected from the group consisting of unmodified alkyl, acrylic, acrylic alkyd or polyester resins;

said resins modified with silicon, isocyanates, isocyanurates, ketimines or oxazolidines;

crosslinked epoxy resins; and

epoxy-crosslinked acrylic and polyester resins.

26. A composition according to claim 25 which is an enamel of high solids content for industrial finishes.

27. A composition according to claim 26 which is a finishing enamel for automobiles.

28. A composition according to claim 27 which is a curable electrocoat composition wherein component (a) is an amino-group containing resin having functional groups that are reactive with an isocyanate and an aromatic polyisocyanate crosslinking agent.

29. A composition according to claim 4 which is a non-gelling liquid coating composition wherein component (a) comprises (A) at least one acrylic monomer, (B) silica and (C) at least one initiator for ultraviolet radication-induced curing of said composition.

30. A composition according to claim 29 which contains a silyl acrylate, a polyfunctional acrylate, silica and a photoinitiator.

31. A composition according to claim 4 wherein component (a) is a polyolefin, polycarbonate, a styrenic, ABS, a nylon (polyamide), a polyester, a polyurethane, a polyacrylate, a rubber modified styrenic, poly(vinyl chloride), poly(vinyl butyral), polyacetal (polyoxymethylene), or other blends or copolymers such as poly(ethylene/1,4-cyclohexylenedimethylene terephthalate) PETG or an ethylene/acrylic acid copolymer or salts thereof (an ionomer).

32. A composition according to claim 31 wherein the polymer is a polyester or a polyacrylate.

33. A composition according to claim 32 wherein the polyester is poly(ethylene terephthalate), poly(butylene terephthalate) or poly(ethylene naphthalenedicarboxylate), or copolymer poly(ethylene/1,4-cyclohexylenedimethylene terephthalate) PETG.

34. A composition according to claim 4 wherein component (a) is a thermoplastic polymer.

35. A composition according to claim 34 wherein the polymer is a polyolefin or polycarbonate.

36. A composition according to claim 35 wherein the polymer is polyethylene or polypropylene.

37. A composition according to claim 4 wherein component (a) is a photographic composition.

38. A composition according to claim 35 wherein the polymer is polycarbonate.

39. A composition according to claim 32 wherein the polymer is a polyacrylate.

40. A composition according to claim 39 wherein the polyacrylate is poly(methyl methacrylate).