Poly-trisaryl-1,3,5-Triazine carbamate ultraviolet light absorbers

• US 6,306,939 B1
• Filed: 06/18/1999
• Issued: 10/23/2001
• Est. Priority Date: 06/22/1998
• Status: Expired due to Fees

• Current Assignee: Strong Trading, Inc.
• Original Assignee: CIBA Specialty Chemicals
• Inventors: Gupta, Ram Baboo, Jakiela, Dennis John
• Primary Examiner(s): SANDERS, KRIELLION ANTIONETTE
• Application Number:
  US09/335,787
• Time in Patent Office: 858 Days
• Field of Search: 524/100, 544/215, 544/216, 252/403
• US Class Current: 524/100
• CPC Class Codes: A61K 8/4966 Triazines or their condensed derivatives
• CPC Class Codes: A61Q 17/04 Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
• CPC Class Codes: C07D 251/24 to three ring carbon atoms
• CPC Class Codes: C08G 18/3851 containing three nitrogen atoms in the ring
• CPC Class Codes: C08G 18/765 alpha, alpha, alpha', alpha', -tetraalkylxylylene diisocyanate or homologues substituted on the aromatic ring
• CPC Class Codes: C08G 18/7893 having three nitrogen atoms in the ring
• CPC Class Codes: C08K 5/3492 Triazines
• CPC Class Codes: C08L 75/04 Polyurethanes
• CPC Class Codes: C09D 175/04 Polyurethanes

Abstract

The present invention relates to novel carbamate containing trisaryl-1,3,5-triazines and the use thereof as an ultraviolet light absorber. In particular, the presently claimed compounds comprise a carbamate triazine polymer which is particularly useful, either alone or in combination with other additives, including other ultraviolet light absorbers and stabilizers, in stabilizing a polymeric film or molded article from degradation due to exposure to actinic radiation.

Claims

1. A compound selected from the group consisting of compounds of formula (I), (II) and (III):

wherein;

(a) A is a polyvalent hydrocarbyl or a polyvalent 1,3,5-triazine;

(b) each X is independently hydrogen, allyl, —

COR^a, —

SO₂R^b, SiR^cR^dR^e, —

PR^fR^g, or —

POR^fR^g;

(c) each of Y and Z is independently an aryl ring of formula (IV);

(d) each R is independently a hydrocarbyl group or a functional hydrocarbyl group; and

is different from each other R group;

each R′

is independently a hydrocarbylene group, a functional hydrocarbylene group or the group —

CH₂CONC₄H₉(CH₂)₂—

;

(e) each R^a is independently C₁-C₈ alkyl, halogen-substituted C₁-C₈ alkyl, C₅-C₁₂ cycloalkyl, C₂-C₈ alkenyl, —

CH₂—

CO—

CH₃, C₇-C₁₂ aralkyl, C₁-C₁₂ alkoxy, or phenyl which is unsubstituted or substituted by C₁-C₁₂ alkyl, C₁-C₄ alkoxy, halogen and/or benzyl;

(f) each R^b is independently C₁-C₁₂ alkyl, C₆-C₁₀ aryl, or C₇-C₁₈ alkylaryl;

(g) each R^c, R^d, and R^e is independently C₁-C₁₈ alkyl, cyclohexyl, phenyl, or C₁-C₁₈ alkoxy;

(h) each R^f and R^g is independently C₁-C₁₂ alkoxy, phenoxy, C₁-C₁₂ alkyl, C₅-C₁₂ cycloalkyl, benzyl, tolyl, or phenyl;

(i) each R¹, R² and R⁴ is independently hydrogen, hydrocarbyl, functional hydrocarbyl, —

O(hydrocarbyl), —

O(functional hydrocarbyl), —

SR, halogen, —

SO₃R, —

COOR, —

COR, —

OCOR, —

NRR or cyano;

(j) each R³ is independently R, —

OR, —

SR, halogen, —

SO₃R, —

COOR, —

COR, —

NRR or cyano; and

(k) n is an integer between 2 and about 50.

2. A compound according to claim 1, selected from the group consisting of compounds of formula (V), (VI) or (VII):

wherein;

(a) A is a polyvalent hydrocarbyl or a heterocyclic ring;

(b) each R is independently selected from a hydrocarbyl group and a functional hydrocarbyl group; and

is different from each other R group;

(c) each R² is independently selected from hydrogen, a hydrocarbyl group of 1 to 24 carbon atoms, a hydrocarbyloxy group of 1 to 24 carbon atoms, and an acyloxy group of 1 to 24 carbon atoms;

(d) each R³ is independently selected from hydrogen, a hydrocarbyl group of 1 to 24 carbon atoms, a functional hydrocarbyl group of 1 to 24 carbon atoms and —

OR; and

(e) n is 2 or 3.

3. A compound according to claim 1, selected from the group consisting of compounds of formula (VIII), (IX) or (X):

wherein;

(a) A is a polyvalent hydrocarbyl or a heterocyclic ring;

(b) each R is independently selected from a hydrocarbyl group and a functional hydrocarbyl group; and

is different from each other R group;

(c) R² is selected from hydrogen, a hydrocarbyl group of 1 to 24 carbon atoms, a hydrocarbyloxy group of 1 to 24 carbon atoms, and an acyloxy group of 1 to 24 carbon atoms;

(d) R³ is selected from hydrogen, a hydrocarbyl group of 1 to 24 carbon atoms, a functional hydrocarbyl group of 1 to 24 carbon atoms and —

OR; and

(e) n is 2 or 3.

4. The compound of claims 2 or 3, wherein each R² is independently selected from hydrogen, an alkyl of 1 to 8 carbon atoms, an alkyloxy of 1 to 8 carbon atoms optionally containing an oxygen atom in the chain, a hydroxyalkyl of 1 to 8 carbon atoms group optionally containing an oxygen atom in the chain, a hydroxyalkyloxy of 1 to 8 carbon atoms group optionally containing an oxygen atom in the chain, and an acyloxy of 2 to 12 carbon atoms and A is selected from the group consisting of:

5. A composition comprising at least one compound of claim 1.

6. The compound of claim 4, wherein each R² is independently selected from hydrogen, R, —

OR and an alkyl of 1 to 4 carbon atoms and A is selected from the group consisting of polyisocyanate residues formed by the reaction of two or more trisaryl-1,3,5-triazine compounds, each having at least one aryl ring with a hydroxyl group para to the point of attachment to the triazine ring, and being further substituted by a hydroxyl functional hydrocarbyl group, with a polyvalent hydrocarbyl compound such as a diisocyanate, a triisocyanate or a polyisocyanate.

7. The compound of claim 6, wherein each R² is independently selected from hydrogen, C₁-C₄ alkoxy and methyl and A is selected from the group consisting of polyisocyanate residues formed by the reaction of two or more trisaryl-1,3,5-triazine compounds, each having at least one aryl ring with a hydroxyl group para to the point of attachment to the triazine ring, and being further substituted by a hydroxyl functional hydrocarbyl group, with a polyvalent hydrocarbyl compound such as a diisocyanate, a triisocyanate or a polyisocyanate.

8. The compound of claims 2 or 3, wherein each R³ is independently selected from hydrogen, an alkyl of 1 to 24 carbon atoms optionally containing an oxygen atom in the chain, a hydroxyalkyl of 1 to 24 carbon atoms group optionally containing an oxygen atom in the chain, R and —

OR.

9. The compound of claim 8, wherein each R³ is independently selected from hydrogen, an alkyl of 1 to 4 carbon atoms and —

OR.

10. The compound of claim 9, wherein each R³ is independently selected from hydrogen, methyl, C₁-C₄ alkoxy and tertiary butyl.

52. An actinic radiation stabilizing composition which comprises a polymer and at least one compound of formula (I), (II) or (III) according to claim 1.

53. The composition of claim 52, wherein said compound is chemically bound to said polymer.

11. A method of stabilizing a material which is subject to degradation by actinic radiation which comprises the addition to said material of an effective amount of at least one compound selected from the group consisting of compounds of formula (I), (II) and (III)

wherein:

(a) A is a polyvalent hydrocarbyl or a polyvalent 1,3,5-triazine;

(b) each X is independently hydrogen, allyl, —

COR^a, —

SO₂R^b, SiR^cR^dR^e, —

PR^fR^g, or —

POR^fR^g;

(c) each of Y and Z is independently an aryl ring of formula (IV)

(d) each R is independently a hydrocarbyl group or a functional hydrocarbyl group; and

is different from each other R group;

each R′

is independently a hydrocarbylene group, a functional hydrocarbylene group or the group —

CH₂CONC₄H₉(CH₂)<sub>2—

;</sub>

(e) each R^a is independently C₁-C₈ alkyl, halogen-substituted C₁-C₈ alkyl, C₅-C₁₂ cycloalkyl, C₂-C₈ alkenyl, —

CH₂—

CO—

CH₃, C₇-C₁₂ aralkyl, C₁-C₁₂ alkoxy, or phenyl which is unsubstituted or substituted by C₁-C₁₂ alkyl, C₁-C₄ alkoxy, halogen and/or benzyl;

(f) each R^b is independently C₁-C₁₂ alkyl, C₆-C₁₀ aryl, or C₇-C₁₈ alkylaryl;

(g) each R^c, R^d, and R^e is independently C₁-C₁₈ alkyl, cyclohexyl, phenyl, or C₁-C₁₈ alkoxy;

(h) each R^f and R^g is independently C₁-C₁₂ alkoxy, phenoxy, C₁-C₁₂ alkyl, C₅-C₁₂ cycloalkyl, benzyl, tolyl, or phenyl;

(i) each R¹, R² and R⁴ is independently hydrogen, hydrocarbyl, functional hydrocarbyl, —

O(hydrocarbyl), —

O(functional hydrocarbyl), —

SR, halogen, —

SO₃R, —

COOR, —

COR, —

OCOR, —

NRR or cyano;

(j) each R³ is independently R, —

OR, —

SR, halogen, —

SO₃R, —

COOR, —

COR, —

NRR or cyano; and

(k) n is an integer between 2 and about 50.

12. The method of claim 11, wherein the compound of formula (I), (II) or (III) is added in an amount from about 0.01 to about 20% by weight based on the weight of the material to be stabilized.

13. The method of claim 11, wherein the compound of formula (I), (II) or (III) is added in an amount from about 0.1 to about 10% by weight based on the weight of the material to be stabilized.

14. The method of claim 13, wherein said material to be stabilized is a polymer.

15. The method of claim 14, wherein said polymer is a thermoplastic polymer.

16. The method of claim 15, wherein said thermoplastic polymer is a polycarbonate.

17. The method of claim 15, wherein said thermoplastic polymer is a polyketone.

18. The method of claim 15, wherein said thermoplastic polymer is a polyamide or polyamide blend.

19. The method of claim 15, wherein said thermoplastic polymer is a polyolefin.

20. The method of claim 15, wherein said thermoplastic polymer is a polyurethane or polyurethane blend.

21. The method of claim 11, which further comprises incorporating into said material at least one additional additive, said additive selected from the group consisting of:

antioxidants, ultraviolet light absorbers, ultraviolet light stabilizers, metal deactivators, phosphites, phosphonites, hydroxylamines, nitrones, thiosynergists, peroxide scavengers, polyamide stabilizers, nucleating agents, fillers, reinforcing agents, plasticizers, lubricants, emulsifiers, pigments, rheological additives, flameproofing agents, antistatic agents, blowing agents, benzofuranones and indolinones.

22. The method of claim 21, wherein said additional additive is a sterically hindered amine or a UV absorber.

23. The method of claim 21, wherein said additional additive is a benzotriazole, benzophenone, oxamide, acrylate or other triazine.

24. The method of claim 22, wherein said sterically hindered amine comprises at least one member of the group consisting of:

bis(2,2,6,6-tetramethylpiperidin-4-yl) sebacate;

bis(2,2,6,6-tetramethylpiperidin-4-yl)succinate;

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

bis(1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl)sebacate;

bis(1,2,2,6,6-pentamethylpiperidin-4-yl) 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-tetramethylpiperidin-4-yl)hexamethylenediamine and 4-tert-octylamino-2,6-dichloro-1,3,5-triazine;

tris(2,2,6,6-tetramethylpiperidin-4-yl) nitrilotriacetate;

tetrakis(2,2,6,6-tetramethylpiperidin-4-yl)-1,2,3,4-butanetetracarboxylate;

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-dione;

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-tetramethylpiperidin-4-yl)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-bis(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-tetramethylpiperidin-4-yl)pyrrolidin-2,5-dione;

3-dodecyl-1-(1,2,2,6,6-pentamethylpiperidin-4-yl)pyrrolidine-2,5-dione;

a mixture of 4-hexadecyloxy- and 4-stearyloxy-2,2,6,6-tetramethylpiperidine;

the condensate of N,N′

-bis(2,2,6,6-tetramethylpiperidin-4-yl)hexamethylenediamine and 4-cyclohexylamino-2,6-dichloro-1,3,5-triazine;

the condensate of 1,2-bis(3-aminopropylamino)ethane, 2,4,6-trichloro-1,3,5-triazine and 4-butylamino-2,2,6,6-tetramethylpiperidine;

N-(2,2,6,6-tetramethylpiperidin-4-yl)-n-dodecylsuccinimide;

N-(1,2,2,6,6-pentamethylpiperidin-4-yl)-n-dodecylsuccinimide;

2-undecyl-7,7,9,9-tetramethyl-1-oxa-3,8-diaza-4-oxospiro[4.5]decane;

the reaction product of 7,7,9,9-tetramethyl-2-cycloundecyl-1-oxa-3,8-diaza-4-oxospiro[4.5]decane and epichlorohydrin; and

derivatives thereof.

25. The method of claim 14, which further comprises forming a shaped article from said polymer.

26. The method of claim 11 which further comprises applying the material, to which an effective amount of a compound of formula (I), (II) or (III) has been added, to the outer surface of a substrate.

27. The method of claim 26, wherein the material is a polymer.

28. The method of claim 27, wherein said stabilized polymer is applied to said substrate in the form of a film.

29. The method of claim 28, wherein said substrate comprises a metallic, wood, ceramic or polymeric material.

30. The method of claim 28, wherein said substrate comprises more than one layer.

31. The method of claim 11, wherein said material comprises a fiber material.

32. The method of claim 31, wherein said fiber material is selected from the group consisting of silk, leather, wool, polyamide, polyurethane, cellulose-containing fiber and blends thereof.

33. The method of claim 11, wherein said material comprises a cosmetic composition.

34. An actinic radiation stabilizing composition which comprises a binder and a compound selected from the group consisting of compounds of formula (I), (II) and (III):

wherein;

(a) A is a polyvalent hydrocarbyl or a polyvalent 1,3,5-triazine;

(b) each X is independently hydrogen, allyl, —

COR^a, —

SO₂R^b, SiR^cR^dR^e, —

PR^fR^g, or —

POR^fR^g;

(c) each of Y and Z is independently an aryl ring of formula (IV)

(d) each R is independently a hydrocarbyl group or a functional hydrocarbyl group; and

is different from each other R group;

each R′

is independently a hydrocarbylene group, a functional hydrocarbylene group or the group —

CH₂CONC₄H₉(CH₂)₂—

;

(e) each R^a is independently C₁-C₈ alkyl, halogen-substituted C₁-C₈ alkyl, C₅-C₁₂ cycloalkyl, C₂-C₈ alkenyl, —

CH₂—

CO—

CH₃, C₇-C₁₂ aralkyl, C₁-C₁₂ alkoxy, or phenyl which is unsubstituted or substituted by C₁-C₁₂ alkyl, C₁-C₄ alkoxy, halogen and/or benzyl;

(f) each R^b is independently C₁-C₁₂ alkyl, C₆-C₁₀ aryl, or C₇-C₁₈ alkylaryl;

(g) each R^c, R^d, and R^e is independently C₁-C₁₈ alkyl, cyclohexyl, phenyl, or C₁-C₁₈ alkoxy;

(h) each R^f and R^g is independently C₁-C₁₂ alkoxy, phenoxy, C₁-C₁₂ alkyl, C₅-C₁₂ cycloalkyl, benzyl, tolyl, or phenyl;

(i) each R¹, R² and R⁴ is independently hydrogen, hydrocarbyl, functional hydrocarbyl, —

O(hydrocarbyl), —

O(functional hydrocarbyl), —

SR, halogen, —

SO₃R, —

COOR, —

COR, —

OCOR, —

NRR or cyano;

(j) each R³ is independently R, —

OR, —

SR, halogen, —

SO₃R, —

COOR, —

COR, —

NRR or cyano; and

(k) n is an integer between 2 and about 50.

35. The composition of claim 34, wherein said composition is a coating composition.

36. The composition of claim 34, wherein the compound of formula (I), (II) or (III) is present in an amount from about 0.01 to about 20% by weight of the binder.

37. The composition of claim 36, wherein the compound of formula (I), (II) or (III) is present in an amount from about 0.1 to about 10% by weight of the binder.

38. The composition of claim 34, wherein said binder comprises a polymer.

39. The composition of claim 34, wherein the binder comprises an alkyd, acrylic, polyester, phenolic, melamine, epoxy or polyurethane resin, or blends thereof.

40. The composition of claim 34, wherein said binder is at least one of:

(a) cold- or hot-crosslinkable alkyd, acrylate, polyester, epoxy or melamine resins or mixtures of such resins;

(b) a two-component polyurethane system comprising hydroxyl-containing acrylate, polyester or polyether resins and aliphatic or aromatic isocyanates, isocyanurates or polyisocyanates;

(c) a one-component polyurethane system comprising blocked isocyanates, isocyanurates or polyisocyanates which are deblocked during baking;

(d) a two-component system comprising (poly)ketimines and aliphatic or aromatic isocyanates, isocyanurates or polyisocyanates;

(e) a two-component system comprising (poly)ketimines and an unsaturated acrylate resin or a polyacetoacetate resin or a methacrylamidoglycolate methyl ester;

(f) a two-component system comprising carboxyl- or amino-containing polyacrylates and polyepoxides;

(g) a two-component system comprising acrylate resins containing anhydride groups and on a polyhydroxy or polyamino component;

(h) a two-component system comprising (poly)oxazolines and acrylate resins containing anhydride groups, or unsaturated acrylate resins, or aliphatic or aromatic isocyanates, isocyanurates or polyisocyanates;

(i) a two-component system comprising unsaturated polyacrylates and polymalonates;

(j) a thermoplastic polyacrylate system comprising thermoplastic acrylate resins or externally crosslinking acrylate resins in combination with etherified melamine resins; and

(k) a system comprising siloxane-modified or fluorine-modified acrylate resins.

41. The composition of claim 40, which further comprises a curing catalyst.

42. The composition of claim 40, wherein said composition is a radiation-curable composition.

43. The composition of claim 40, wherein said composition further comprises an additional stabilizer against actinic radiation.

44. The composition of claim 43, wherein said additional stabilizer is present in an amount from about 0.05 to about 5% by weight of the binder.

45. The composition of claim 43, wherein said additional stabilizer is a sterically hindered amine or a UV absorber.

46. The composition of claim 45, wherein said sterically hindered amine comprises at least one member of the group consisting of:

bis(2,2,6,6-tetramethylpiperidin-4-yl) sebacate;

bis(2,2,6,6-tetramethylpiperidin-4-yl)succinate;

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

bis(1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl)sebacate;

bis(1,2,2,6,6-pentamethylpiperidin-4-yl) 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-tetramethylpiperidin-4-yl)hexamethylenediamine and 4-tert-octylamino-2,6-dichloro-1,3,5-triazine;

tris(2,2,6,6-tetramethylpiperidin-4-yl) nitrilotriacetate;

tetrakis(2,2,6,6-tetramethylpiperidin-4-yl)-1,2,3,4-butanetetracarboxylate;

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-dione;

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-tetramethylpiperidin-4-yl)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-bis(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-tetramethylpiperidin-4-yl)pyrrolidin-2,5-dione;

3-dodecyl-1-(1-acetyl-2,2,6,6-tetramethylpiperidin-4-yl)pyrrolidin-2,5-dione;

3-dodecyl-1-(1,2,2,6,6-pentamethylpiperidin-4-yl)pyrrolidine-2,5dione;

a mixture of 4-hexadecyloxy- and 4-stearyloxy-2,2,6,6-tetramethylpiperidine;

the condensate of N,N′

-bis(2,2,6,6-tetramethylpiperidin-4-yl)hexamethylenediamine and 4-cyclohexylamino-2,6-dichloro-1,3,5-triazine;

the condensate of 1,2-bis(3-aminopropylamino)ethane, 2,4,6-trichloro-1,3,5-triazine and 4-butylamino-2,2,6,6-tetramethylpiperidine;

N-(2,2,6,6-tetramethyl piperidin-4-yl)-n-dodecylsuccinimide;

N-(1,2,2,6,6-pentamethylpiperidin-4-yl)-n-dodecylsuccinimide;

2-undecyl-7,7,9,9-tetramethyl-1-oxa-3,8-diaza-4-oxospiro[4.5]decane;

the reaction product of 7,7,9,9-tetramethyl-2-cycloundecyl-1-oxa-3,8-diaza-4-oxospiro[4.5]decane and epichlorohydrin;

derivatives thereof, and mixtures thereof.

47. The composition of claim 45, wherein said sterically hindered amine comprises at least one member of the group consisting of:

bis(2,2,6,6-tetramethylpiperidin-4-yl) sebacate;

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

bis(1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl)sebacate;

the condensate of N,N′

-bis(2,2,6,6-tetramethylpiperidin-4-yl)hexamethylenediamine and 4-tert-octylamino-2,6-dichloro-1,3,5-triazine;

the condensate of N,N′

-bis(2,2,6,6-tetramethylpiperidin-4-yl)hexamethylenediamine and 4-morpholino-2,6-dichloro-1,3,5-triazine;

3-dodecyl-1-(2,2,6,6-tetramethylpiperidin-4-yl)pyrrolidin-2,5-dione;

3-dodecyl-1-(1-acetyl-2,2,6,6-tetramethylpiperidin-4-yl)pyrrolidin-2,5-dione;

a mixture of 4-hexadecyloxy- and 4-stearyloxy-2,2,6,6-tetramethylpiperidine, and mixtures thereof.

48. The composition of claim 45, wherein said benzotriazole comprises at least one member of the group consisting of:

2-(2′

-hydroxy-5′

-methylphenyl)-benzotriazole;

2-(3′

,5′

-di-tert-butyl-2′

-hydroxyphenyl)benzotriazole;

2-(5′

-tert-butyl-2′

-hydroxyphenyl)benzotriazole;

2-(2′

-hydroxy-5′

-(1,1,3,3-tetramethylbutyl)phenyl)benzotriazole;

2-(3′

,5′

-di-tert-butyl-2′

-hydroxyphenyl)-5-chlorobenzotriazole;

2-(3′

-tert-butyl-2′

-hydroxy-5′

-methylphenyl)-5-chloro-benzotriazole;

2-(3′

-sec-butyl-5′

-tert-butyl-2′

-hydroxyphenyl)-benzotriazole;

2-(2′

-hydroxy-4′

-octoxyphenyl)benzotriazole;

2-(3′

,5′

-di-tert-amyl-2′

-hydroxphenyl)benzotriazole;

2-(3′

,5′

-bis(α

,α

-dimethylbenzyl)-2′

-hydroxyphenyl)-benzotriazole;

a mixture of 2-(3′

-tert-butyl-2′

-hydroxy-5′

-(2-octyloxycarbonylethyl)phenyl)-5-chloro-benzotriazole, 2-(3′

-tert-butyl-5′

-[2-(2-ethylhexyloxy)-carbonylethyl]-2′

-hydroxyphenyl)-5-chloro-benzotriazole, 2-(3′

-tert-butyl-2′

-hydroxy-5′

-(2-methoxycarbonylethyl)phenyl)-5-chloro-benzotriazole, 2-(3′

-tert-butyl-2′

-hydroxy-5′

-(2-methoxycarbonylethyl)phenyl)benzotriazole, 2-(3′

-tert-butyl-2′

-hydroxy-5′

-(2-octyloxycarbonylethyl)phenyl)benzotriazole, 2-(3′

-tert-butyl-5′

-[2-(2-ethylhexyloxy)carbonylethyl]-2′

-hydroxyphenyl)benzotriazole, 2-(3′

-dodecyl-2′

-hydroxy-5′

-methylphenyl)benzotriazole and 2-(3′

-tert-butyl-2′

-hydroxy-5′

-(2-isooctyloxycarbonylethyl)phenylbenzotriazole;

2,2-methylenebis[4(1,1,3,3-tetramethylbutyl)-6-benzotriazol-2-ylphenol];

the transesterification product of 2-[3′

-tert-butyl-5′

-(2-methoxycarbonylethyl)-2′

-hydroxyphenyl]benzotriazole with polyethylene glycol 300;

[R—

CH₂CH—

COO(CH₂)₃]₂—

where R=3′

-tert-butyl-4′

-hydroxy-5′

-2H-benzotriazol-2-ylphenyl; and

derivatives thereof.

49. The composition of claim 45, wherein said benzotriazole comprises at least one member of the group consisting of:

2-(2′

-hydroxy-5′

-(1,1,3,3-tetramethylbutyl)phenyl)benzotriazole;

2-(3′

,5′

-di-tert-amyl-2′

-hydroxphenyl)benzotriazole;

2-(3′

,5′

-bis(α

,α

-dimethylbenzyl)-2′

-hydroxyphenyl)benzotriazole;

2-(3′

-tert-butyl-2′

-hydroxy-5′

-(2-octyloxycarbonylethyl)phenyl)benzotriazole, the transesterification product of 2-[3′

-tert-butyl-5′

-(2-methoxycarbonylethyl)-2′

-hydroxyphenyl]benzotriazole with polyethylene glycol 300 and mixtures thereof.

50. The composition of claim 40, wherein said composition is a coating composition.

51. A photographic material comprising the light stabilizing composition of claim 40.