Process for the preparation of a hindered amine light stabilizer salt

• US 20040183053A1
• Filed: 03/20/2003
• Published: 09/23/2004
• Est. Priority Date: 03/20/2003
• Status: Abandoned Application

• Current Assignee: Gether Irick Jr, Greg Alan King, Jason Clay Pearson, John Peter Mykytka, Max Allen Weaver
• Original Assignee: Gether Irick Jr, Greg Alan King, Jason Clay Pearson, John Peter Mykytka, Max Allen Weaver
• Inventors: King, Greg Alan, Weaver, Max Allen, Pearson, Jason Clay, Mykytka, John Peter, Irick, Gether Jr.
• Application Number:
  US10/392,575
• Publication Number:
  US 20040183053A1
• Time in Patent Office: Days
• US Class Current: 252/400.21
• CPC Class Codes: C07D 211/76 attached in position 2 or 6
• CPC Class Codes: C07D 401/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 401/14 containing three or more hetero rings

Abstract

This invention relates to a process for the preparation of an addition salt of at least one hindered amine light stabilizer and at least one acidic phosphorus containing compound. The process comprises the step of combining at least one hindered amine light stabilizer and an acidic phosphorus containing compound so that an addition salt is formed as an isolatable solid.

Claims

1. A process for the preparation of an addition salt of at least one hindered amine light stabilizer and at least one acidic phosphorus containing compound comprising the step of combining the following:

(A) at least one acidic phosphorus containing compound selected from compounds having the formulae;

wherein

R₁ and R₂ are independently selected from hydrogen, C₁-C₂₂-alkyl, substituted C₁-C₂₂-alkyl, C₃-C₈-cycloalkyl, substituted C₃-C₈-cycloalkyl, heteroaryl, and aryl;

n is 2 to 500; and

(B) at least one hindered amine light stabilizer selected from compounds having the formulae;

wherein

R₃, R₄, R₅, and R₆ are independently selected from hydrogen, C₁-C₂₂-alkyl, substituted C₁-C₂₂-alkyl, C₃-C₈-cycloalkyl, substituted C₃-C₈-cycloalkyl, heteroaryl, aryl;

R₇ is selected from hydrogen, —

OR₆, C₁-C₂₂-alkyl, substituted C₁-C₂₂-alkyl, C₃-C₈-cycloalkyl, substituted C₃-C₈-cycloalkyl;

R₈ is selected from hydrogen;

C₁-C₂₂-alkyl, substituted C₁-C₂₂-alkyl, C₃-C₈-cycloalkyl, substituted C₃-C₈-cycloalkyl, heteroaryl, aryl, —

Y₁—

R₁ or a succinimido group having the formula

R₉ and R₁₀ are independently selected from hydrogen, C₁-C₂₂-alkyl, substituted C₁-C₂₂-alkyl, C₃-C₈-cycloalkyl, and substituted C₃-C₈-cycloalkyl;

R₉ and R₁₀ may collectively represent a divalent group forming a ring with the nitrogen atom to which they are attached;

L₁ is a divalent linking group selected from C₂-C₂₂-alkylene;

—

(CH₂CH₂—

Y₁)_1-3—

CH₂CH₂—

;

C₃-C₈-cycloalkylene;

arylene;

or —

CO—

L₂—

OC—

;

L₂ is selected from C₁-C₂₂-alkylene, arylene, —

(CH₂CH₂—

Y₁)_1-3—

CH₂CH₂— and

C₃-C₈-cycloalkylene;

Y₁ is selected from —

OC(O)—

, —

NHC(O)—

, —

O—

, —

S—

, —

N(R₁)—

;

Y₂ is selected from —

O—

or —

N(R₁)—

;

Z is a positive integer of up to about 20;

m₁, is selected from 0 to about 10;

n1 is a positive integer selected from 2 to about 12;

R₁₁, and R₁₂ are independently selected from hydrogen, C₁-C₂₂-alkyl, substituted C₁-C₂₂-alkyl, C₃-C₈-cycloalkyl, substituted C₃-C₈-cycloalkyl, heteroaryl, aryl, and radical A wherein radical A is selected from the following structures;

Radical A structures wherein * designates the position of attachment

wherein at least one of R₁₁ and R₁₂ is also a radical A; and

wherein the ratio of the number of phosphorus atoms in the acidic phosphorus-containing compound to the number of basic nitrogen atoms in the HALS is about 0.25 to about 2;

wherein the addition salt of components (A) and (B) is formed.

2. The process of claim 1 wherein the ratio of the number of phosphorus atoms in the acidic phosphorus containing compound to the number of basic nitrogen atoms in the hindered amine light stabilizer is about 0.25 to about 2.

3. The process of claim 2 wherein the ratio of the number of phosphorus atoms in the acidic phosphorus containing compound to the number of basic nitrogen atoms in the hindered amine light stabilizer is about 0.50 to about 1.1.

4. The process of claim 1 comprising the following steps:

(1) at least one acidic phosphorus containing compound (Component A) is dissolved in a polar solvent (I);

(2) at least one hindered amine light stabilizer of (Component B) is separately dissolved in an aromatic hydrocarbon solvent (II); and

, subsequently,

(3) Components (A) and (B) are mixed to form a homogenous solution of the addition salt.

5. The process of claim 4 additionally comprising step 4 where the homogeneous solution of step 3 is subsequently then mixed with an aliphatic nonpolar solvent (III) so that the addition salt precipitates.

6. The process of claim 4 wherein the polar solvent (I) is one or more polar organic solvents having a dielectric constant of greater than about 3.0 at 298°

K.

7. The process of claim 6 wherein said polar solvents (I) are selected from one or more of the group consisting of methanol, ethanol, n-propanol, isopropanol, n-butanol, t-butanol, isobutanol, 2-butanol, n-hexanol, and octanol.

8. The process of claim 7 wherein said polar solvents (I) is selected from methanol and isopropanol.

9. The process of claim 4 wherein the acidic phosphorus containing compound is present in the polar solvent (I) in the amount of 0.1 to 50 weight percent.

10. The process of claim 9 wherein the acidic phosphorus containing compound is present in the polar solvent (I) in the amount of 25 to 35 weight percent.

11. The process of claim 4 wherein the aromatic hydrocarbon solvent (II) is selected from the group consisting of toluene, xylene, and benzene.

12. The process of claim 5 wherein the aliphatic nonpolar solvent (III) is selected from the group consisting of pentane, heptane, hexane, octane, isooctane, carbon tetrachloride, chloroform, methylene chloride, cyclobutane, cyclopentane, cyclohexane, and 1,3-dimethyl cyclohexane.

13. The process of claim 12 wherein the aliphatic nonpolar solvent (III) is selected from heptane, hexane, and octane.

14. The process of claim 13 wherein the aliphatic nonpolar solvent I(III) is heptane.

15. The process of claim 4 wherein the hindered amine light stabilizer is present in the aromatic hydrocarbon solvent (II) in the amount of 0.1 to 45 weight percent.

16. The process of claim 15 wherein the hindered amine light stabilizer is present in the aromatic hydrocarbon solvent (II) in the amount of 10 to 30 weight percent.

17. The process of claim 4 wherein the aromatic hydrocarbon solvent (II) is combined with the hindered amine light stabilizer in a ratio by weight of hindered amine light stabilizer to aromatic hydrocarbon solvent of 1:

5 to 1;

20

18. The process of claim 4 wherein the weight ratio of the polar solvent(s) (I) to the aromatic hydrocarbon solvent(s) (II) is 0.075 to 1.

19. The process of claim 4 wherein the total weight percentage of the salt formed is 0.1 to 30 weight percent based on the total combined weight of the polar solvent(s) (I) and the aromatic hydrocarbon solvent(s) (II).

20. The process of claim 5 wherein at least one aliphatic non-polar solvents (III) are added to that the total weight percent of salt in the solvent mixture is less than 15 weight percent based on the total weight of the composition.

21. The process of claim 5 further comprising the step of isolating the addition salt precipitate.

22. A process for the preparation of an addition salt of at least one hindered amine light stabilizer and at least one acidic phosphorus containing compound comprising the following steps:

(1) the acidic phosphorus containing compound is phosphorous acid which is dissolved in at least one polar solvent (I) wherein the polar solvent(s) (I) is selected from methanol, ethanol, n-propanol, isopropanol, n-butanol, t-butanol, isobutanol, 2-butanol, n-hexanol, and octanol;

(2) at least one hindered amine light stabilizer which is dissolved in at least one aromatic hydrocarbon solvent (II) wherein the at least one hindered amine light stabilizer is selected compounds having the formulae;

wherein

R₁ and R₂ are independently selected from hydrogen, C₁-C₂₂-alkyl, substituted C₁-C₂₂-alkyl, C₃-C₈-cycloalkyl, substituted C₃-C₈-cycloalkyl, heteroaryl, and aryl;

R₃, R₄, R₅, and R₆ are independently selected from hydrogen, C₁-C₂₂-alkyl, substituted C₁-C₂₂-alkyl, C₃-C₈-cycloalkyl, substituted C₃-C₈-cycloalkyl, heteroaryl, aryl;

R₇ is selected from hydrogen, —

OR₆, C₁-C₂₂-alkyl, substituted C₁-C₂₂-alkyl, C₃-C₈-cycloalkyl, substituted C₃-C₈-cycloalkyl;

R₈ is selected from hydrogen;

C₁-C₂₂-alkyl, substituted C₁-C₂₂-alkyl, C₃-C₈-cycloalkyl, substituted C₃-C₈-cycloalkyl, heteroaryl, aryl, —

Y₁—

R₁ or a succinimido group having the formula

R₉ and R₁₀ are independently selected from hydrogen, C₁-C₂₂-alkyl, substituted C₁-C₂₂-alkyl, C₃-C₈-cycloalkyl, and substituted C₃-C₈-cycloalkyl;

R₉ and R₁₀ may collectively represent a divalent group forming a ring with the nitrogen atom to which they are attached;

L₁ is a divalent linking group selected from C₂-C₂₂-alkylene;

—

(CH₂CH₂—

Y₁)_1-3—

CH₂CH₂—

;

C₃-C₈-cycloalkylene;

arylene;

or —

CO—

L₂—

OC—

;

L₂ is selected from C₁-C₂₂-alkylene, arylene, —

(CH₂CH₂—

Y₁)_1-3—

CH₂CH₂— and

C₃-C₈-cycloalkylene;

Y₁ is selected from —

OC(O)—

, —

NHC(O)—

, —

O—

, —

S—

, —

N(R₁)—

;

Y₂ is selected from —

O—

or —

N(R₁)—

;

Z is a positive integer of up to about 20;

m₁, is selected from 0 to about 10;

n1 is a positive integer selected from 2 to about 12;

R₁₁, and R₁₂ are independently selected from hydrogen, C₁-C₂₂-alkyl, substituted C₁-C₂₂-alkyl, C₃-C₈-cycloalkyl, substituted C₃-C₈-cycloalkyl, heteroaryl, aryl, and radical A wherein radical A is selected from the following structures;

Radical A structures wherein * designates the position of attachment.

wherein at least one of R₁₁ and R₁₂ is an A radical;

wherein the addition salt of components (A) and (B) is formed;

and wherein the at least one aromatic hydrocarbon solvent (II) is selected from toluene, xylene and benzene;

(3) components (A) and (B) are subsequently mixed to form a homogenous solution of the addition salt.; and

(4) the homogeneous solution of step (3) is subsequently mixed with an nonpolar aliphatic hydrocarbon solvent (III) so that the addition salt of components (A) and (B) precipitates.

23. The process of claim 22 wherein the ratio of the number of phosphorus atoms in the phosphorous acid to the number of basic nitrogen atoms in the hindered amine light stabilizer is about 0.25 to about 2.

24. The process of claim 23 wherein the ratio of the number of phosphorus atoms in the phosphorous acid to the number of basic nitrogen atoms in the hindered amine light stabilizer is about 0.50 to about 1.1.

25. The process of claim 22 wherein said polar solvents (I) is selected from methanol and isopropanol.

26. The process of claim 22 wherein the acidic phosphorus containing compound is present in the polar solvent (I) in the amount of 0.1 to 50 weight percent.

27. The process of claim 26 wherein the acidic phosphorus containing compound is present in the polar solvent (I) in the amount of 25 to 35 weight percent.

28. The process of claim 22 wherein the aromatic hydrocarbon solvent (II) is selected from the group consisting of toluene, xylene, and benzene.

29. The process of claim 22 wherein the nonpolar aliphatic hydrocarbon solvent (III) is selected from the group consisting of pentane, heptane, hexane, octane, isooctane, cyclobutane, cyclopentane, cyclohexane, and 1,3-dimethyl cyclohexane.

30. The process of claim 29 wherein the aliphatic nonpolar solvent (III) is selected from heptane, hexane, and octane.

31. The process of claim 30 wherein the aliphatic nonpolar solvent I(III) is heptane.

32. The process of claim 22 wherein the hindered amine light stabilizer is present in the aromatic hydrocarbon solvent (II) in the amount of 5 to 45 weight percent.

33. The process of claim 32 wherein the hindered amine light stabilizer is present in the aromatic hydrocarbon solvent (II) in the amount of 10 to 30 weight percent.

34. The process of claim 22 wherein the aromatic hydrocarbon solvent (II) is combined with the hindered amine light stabilizer in a ratio by weight of hindered amine light stabilizer to aromatic hydrocarbon solvent of 1:

20 to 1;

2.5.

35. The process of claim 22 wherein the weight ratio of the polar solvent(s) (I) to the aromatic hydrocarbon solvent(s) (II) is 0.075 to 1.

36. The process of claim 22 wherein the total weight percentage of the salt formed is 5 to 30 weight percent based on the total combined weight of the polar solvent(s) (I), the aromatic hydrocarbon solvent(s) (II), and the nonpolar aliphatic hydrocarbon solvent (III).

37. The process of claim 22 wherein one or more aliphatic non-polar solvents (III) are added to that the total weight percent of salt in the solvent mixture is less than 15 weight percent.

38. The process of claim 22 further comprising the step of isolating the addition salt precipitate.

39. The process of claim 22 wherein the temperature of the reaction is 15°

C. to 65°

C.

40. A process for the preparation of an addition salt of at least one hindered amine light stabilizer and phosphorous acid comprising the following steps:

(1) phosphorous acid is dissolved in at least one polar solvent (I) selected from methanol and isopropanol; and

(2) at least one hindered amine light stabilizer is dissolved in at least one aromatic hydrocarbon solvent (II) wherein the hindered amine light stabilizer has the formula;

wherein R₃=R₄=R₅=R₆=R₇=methyl, (R₃)(R₄)N—

collectively represent morpholino, L₁ is C₁ to C₆ alkylene, and Z is 1 to 6;

wherein the at least one aromatic hydrocarbon solvent (II) is selected from toluene, xylene, and benzene;

(3) components (A) and (B) are subsequently mixed to form a homogenous solution of the addition salt.; and

(4) the homogeneous solution of step (3) is subsequently mixed with heptane;

wherein the addition salt of components (A) and (B) precipitates.

41. A process for the preparation of an addition salt of at least one hindered amine light stabilizer and at least one acidic phosphorus containing compound comprising the step of mixing, grinding, and/or pulverizing and, subsequently, melt extruding the following:

(A) at least one acidic phosphorus containing compound selected from compounds having the formulae;

wherein

R₁ and R₂ are independently selected from hydrogen, C₁-C₂₂-alkyl, substituted C₁-C₂₂-alkyl, C₃-C₈-cycloalkyl, substituted C₃-C₈-cycloalkyl, heteroaryl, and aryl;

n is 2 to 500; and

(B) at least one hindered amine light stabilizer selected from compounds having the formulae;

wherein

R₃, R₄, R₅, and R₆ are independently selected from hydrogen, C₁-C₂₂-alkyl, substituted C₁-C₂₂-alkyl, C₃-C₈-cycloalkyl, substituted C₃-C₈-cycloalkyl, heteroaryl, aryl;

R₇ is selected from hydrogen, —

OR₆, C₁-C₂₂-alkyl, substituted C₁-C₂₂-alkyl, C₃-C₈-cycloalkyl, substituted C₃-C₈-cycloalkyl;

R₈ is selected from hydrogen;

C₁-C₂₂-alkyl, substituted C₁-C₂₂-alkyl, C₃-C₈-cycloalkyl, substituted C₃-C₈-cycloalkyl, heteroaryl, aryl, —

Y₁—

R₁ or a succinimido group having the formula

R₉ and R₁₀ are independently selected from hydrogen, C₁-C₂₂-alkyl, substituted C₁-C₂₂-alkyl, C₃-C₈-cycloalkyl, and substituted C₃-C₈-cycloalkyl;

R₉ and R₁₀ may collectively represent a divalent group forming a ring with the nitrogen atom to which they are attached;

L₁ is a divalent linking group selected from C₂-C₂₂-alkylene;

—

(CH₂CH₂—

Y₁)_1-3—

CH₂CH₂—

;

C₃-C₈-cycloalkylene;

arylene;

or —

CO—

L₂—

OC—

;

L₂ is selected from C₁-C₂₂-alkylene, arylene, —

(CH₂CH₂—

Y₁)_1-3—

CH₂CH₂— and

C₃-C₈-cycloalkylene;

Y₁ is selected from —

OC(O)—

, —

NHC(O)—

, —

O—

, —

S—

, —

N(R₁)—

;

Y₂ is selected from —

O—

or —

N(R₁)—

;

Z is a positive integer of up to about 20;

m₁, is selected from 0 to about 10;

n1 is a positive integer selected from 2 to about 12;

R₁₁, and R₁₂ are independently selected from hydrogen, C₁-C₂₂-alkyl, substituted C₁-C₂₂-alkyl, C₃-C₈-cycloalkyl, substituted C₃-C₈-cycloalkyl, heteroaryl, aryl, and radical A wherein radical A is selected from the following structures;

Radical A structures wherein * designates the position of attachment

wherein at least one of R₁₁ and R₁₂ is also a radical A; and

wherein the ratio of the number of phosphorus atoms in the acidic phosphorus-containing compound to the number of basic nitrogen atoms in the HALS is 0.5 to about 1.1;

(C) a polymer selected from polyesters and polycarbonates; and

wherein the addition salt of components (A) and (B) is formed.

42. The process of claim 41 wherein:

(A) the phosphorus containing compound is phosphorous acid; and

(B) the hindered amine light stabilizer has the formula;

wherein R₃=R₄=R₅=R₆=R₇=methyl, (R₃)(R₄)N—

collectively represent morpholino, L₁ is C₁ to C₆ alkylene, and Z is 1 to 6; and

(C) the polymer is a polyester.

43. The process of claim 41 wherein the ratio of the number of phosphorus atoms in the phosphorous acid to the number of basic nitrogen atoms in the hindered amine light stabilizer is about 0.25 to about 2.

44. The process of claim 41 wherein the ratio of the number of phosphorus atoms in the phosphorous acid to the number of basic nitrogen atoms in the hindered amine light stabilizer is about 0.5 to about 1.1.

45. A process for the preparation of an addition salt of at least one hindered amine light stabilizer and at least one acidic phosphorus containing compound comprising the following steps:

(1) component (A) is dissolved in a polar solvent (I) and component (B) is dissolved in an non-polar aliphatic hydrocarbon solvent (III) which is immiscible with polar solvent (I);

(2) components (A) and (B) are mixed to form a biphasic mixture wherein the addition salt is in the polar solvent phase;

(3) the biphasic mixture is separate into the two solutions of step 2;

(4) feeding the polar solution of step 3 to a vessel containing the nonpolar solvent of step (3) and vaporizing polar solvent (I) as the polar solvent of step 3 is added to the vessel to produce a slurry of the salt in the nonpolar aliphatic hydrocarbon solvent (III);

wherein component (A) is selected from compounds having the formulae;

wherein

R₁ and R₂ are independently selected from hydrogen, C₁-C₂₂-alkyl, substituted C₁-C₂₂-alkyl, C₃-C₈-cycloalkyl, substituted C₃-C₈-cycloalkyl, heteroaryl, and aryl;

n is 2 to 500; and

wherein component (B) is selected from compounds having the formulae;

wherein

R₁ and R₂ are independently selected from hydrogen, C₁-C₂₂-alkyl, substituted C₁-C₂₂-alkyl, C₃-C₈-cycloalkyl, substituted C₃-C₈-cycloalkyl, heteroaryl, and aryl;

R₃, R₄, R₅, and R₆ are independently selected from hydrogen, C₁-C₂₂-alkyl, substituted C₁-C₂₂-alkyl, C₃-C₈-cycloalkyl, substituted C₃-C₈-cycloalkyl, heteroaryl, aryl;

R₇ is selected from hydrogen, —

OR₆, C₁-C₂₂-alkyl, substituted C₁-C₂₂-alkyl, C₃-C₈-cycloalkyl, substituted C₃-C₈-cycloalkyl;

R₈ is selected from hydrogen;

C₁-C₂₂-alkyl, substituted C₁-C₂₂-alkyl, C₃-C₈-cycloalkyl, substituted C₃-C₈-cycloalkyl, heteroaryl, aryl, —

Y₁—

R₁ or a succinimido group having the formula

R₉ and R₁₀ are independently selected from hydrogen, C₁-C₂₂-alkyl, substituted C₁-C₂₂-alkyl, C₃-C₈-cycloalkyl, and substituted C₃-C₈-cycloalkyl;

R₉ and R₁₀ collectively represent a divalent group forming a ring with the nitrogen atom to which they are attached;

L₁ is a divalent linking group selected from C₂-C₂₂-alkylene;

—

(CH₂CH₂—

Y₁)_1-3—

CH₂CH₂—

;

C₃-C₈-cycloalkylene;

arylene;

or —

CO—

L₂—

OC—

;

L₂ is selected from C₁-C₂₂-alkylene, arylene, —

(CH₂CH₂—

Y₁)_1-3—

CH₂CH₂— and

C₃-C₈-cycloalkylene;

Y₁ is selected from —

OC(O)—

, —

NHC(O)—

, —

O—

, —

S—

, —

N(R₁)—

;

Y₂ is selected from —

O—

or —

N(R₁)—

;

Z is a positive integer of up to about 20;

m₁, is selected from 0 to about 10;

n1 is a positive integer selected from 2 to about 12;

R₁₁ and R₁₂ are independently selected from hydrogen, C₁-C₂₂-alkyl, substituted C₁-C₂₂-alkyl, C₃-C₈-cycloalkyl, substituted C₃-C₈-cycloalkyl, heteroaryl, aryl, and radical A wherein at least one of R₁₁ and R₁₂ is also a Radical A selected from the following structures;

Radical A structures wherein * designates the position of attachment;

wherein the addition salt of components (A) and (B) is formed.

46. The process of claim 45 wherein the acidic phosphorus containing compound is phosphorous acid and ratio of the number of phosphorus atoms in the phosphorous acid to the number of basic nitrogen atoms in the hindered amine light stabilizer is about 0.25 to about 2.

47. The process of claim 46 wherein the ratio of the number of phosphorus atoms in the acid phosphorus containing compound to the number of basic nitrogen atoms in the hindered amine light stabilizer is about 0.50 to about 1.1.

48. The process of claim 45 wherein:

(A) the acidic phosphorus containing compound is phosphorous acid which is dissolved in at least one polar solvent (I) selected from methanol and isopropanol; and

(B) the hindered amine light stabilizer is dissolved in heptane and is selected from the formula;

wherein R₃=R₄=R₅=R₆=R₇=methyl, (R₃)(R₄)N—

collectively represent morpholino, L₁ is C₁ to C₆ alkylene, and Z is 1 to 6.

49. The process of claim 48 wherein the polar solvent (I) is methanol.

50. The process of claim 45 wherein the acidic phosphorus containing compound is present in the polar solvent (I) in the amount of 10 to 50 weight percent.

51. The process of claim 50 wherein the acidic phosphorus containing compound is present in the polar solvent (I) in the amount of 25 to 35 weight percent.

52. The process of claim 45 wherein the nonpolar aliphatic hydrocarbon solvent (III) is selected from the group consisting of pentane, heptane, hexane, octane, isooctane, carbon tetrachloride, chloroform, methylene chloride, cyclobutane, cyclopentane, cyclohexane, and 1,3-dimethyl cyclohexane.

53. The process of claim 52 wherein the aliphatic nonpolar solvent (III) is selected from heptane, octane, and hexane.

54. The process of claim 53 wherein the nonpolar aliphatic hydrocarbon solvent (III) is heptane.

55. The process of claim 53 wherein the total weight percent of salt in the total solvent mixture of step (3) is between 5 and 30 weight percent.

56. A process for the preparation of an addition salt of at least one hindered amine light stabilizer and at least one acidic phosphorus containing compound comprising the following steps:

(1) at least one acidic phosphorus containing compound (Component A) and at least one at least one hindered amine light stabilizer (Component B) is mixed in a polar solvent until a homogeneous solution is obtained;

(2) the acid addition salt is isolated by the process of spray drying;

wherein component (A) is selected from compounds having the formulae;

wherein

R₁ and R₂ are independently selected from hydrogen, C₁-C₂₂-alkyl, substituted C₁-C₂₂-alkyl, C₃-C₈-cycloalkyl, substituted C₃-C₈-cycloalkyl, heteroaryl, and aryl;

n is 2 to 500; and

wherein component (B) is selected from compounds having the formulae;

wherein

R₁ and R₂ are independently selected from hydrogen, C₁-C₂₂-alkyl, substituted C₁-C₂₂-alkyl, C₃-C₈-cycloalkyl, substituted C₃-C₈-cycloalkyl, heteroaryl, and aryl;

R₃, R₄, R₅, and R₆ are independently selected from hydrogen, C₁-C₂₂-alkyl, substituted C₁-C₂₂-alkyl, C₃-C₈-cycloalkyl, substituted C₃-C₈-cycloalkyl, heteroaryl, aryl;

R₇ is selected from hydrogen, —

OR₆, C₁-C₂₂-alkyl, substituted C₁-C₂₂-alkyl, C₃-C₈-cycloalkyl, substituted C₃-C₈-cycloalkyl;

R₈ is selected from hydrogen;

C₁-C₂₂-alkyl, substituted C₁-C₂₂-alkyl, C₃-C₈-cycloalkyl, substituted C₃-C₈-cycloalkyl, heteroaryl, aryl, —

Y—

R₁ or a succinimido group having the formula

R₉ and R₁₀ are independently selected from hydrogen, C₁-C₂₂-alkyl, substituted C₁-C₂₂-alkyl, C₃-C₈-cycloalkyl, and substituted C₃-C₈-cycloalkyl;

R₉ and R₁₀ collectively represent a divalent group forming a ring with the nitrogen atom to which they are attached;

L₁ is a divalent linking group selected from C₂-C₂₂-alkylene;

—

(CH₂CH₂—

Y₁)_1-3—

CH₂CH₂—

;

C₃-C₈-cycloalkylene;

arylene;

or —

CO—

L₂—

OC—

;

L₂ is selected from C₁-C₂₂-alkylene, arylene, —

(CH₂CH₂—

Y₁)_1-3—

CH₂CH₂— and

C₃-C₈-cycloalkylene;

Y₁ is selected from —

OC(O)—

, —

NHC(O)—

, —

O—

, —

S—

, —

N(R₁)—

;

Y₂ is selected from —

O—

or —

N(R₁)—

;

Z is a positive integer of up to about 20;

m₁, is selected from 0 to about 10;

n1 is a positive integer selected from 2 to about 12;

R₁₁ and R₁₂ are independently selected from hydrogen, C₁-C₂₂-alkyl, substituted C₁-C₂₂-alkyl, C₃-C₈-cycloalkyl, substituted C₃-C₈-cycloalkyl, heteroaryl, aryl, and radical A wherein at least one of R₁₁ and R₁₂ is also a Radical A selected from the following structures;

Radical A structures wherein * designates the position of attachment;

wherein the addition salt of components (A) and (B) is formed.

57. The process of claim 56 wherein the acidic phosphorus containing compound is phosphorous acid.

58. The process of claim 57 wherein the hindered amine light stabilizer is selected from the formula:

59. The process of claim 58 wherein the polar solvent is methanol or water.

60. The process of claim 59 wherein the hindered amine light stabilizer and phosphorous acid comprise from 1 to 30 percent of the solution by weight.