Liquid 2-(2-hydroxy-3-higher branched alkyl-5-methyl-phenyl)-2H-benzotriazole mixtures, stabilized compositions and processes for preparing liquid mixtures

• US 4,675,352 A
• Filed: 11/20/1985
• Issued: 06/23/1987
• Est. Priority Date: 01/22/1985
• Status: Expired due to Term

• Current Assignee: Ciba Specialty Chemicals Corp (BASF SE)
• Original Assignee: Ciba-Geigy Corporation (Novartis Ag)
• Inventors: Detlefsen, Robert E., Winter, Roland A. E.
• Primary Examiner(s): Kight, John
• Assistant Examiner(s): Morgan, Kriellion
• Application Number:
  US06/799,768
• Time in Patent Office: 580 Days
• Field of Search: 252/401, 524/91, 548/257, 548/260
• 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

Liquid 2-(2-hydroxy-3-higher branched alkyl-5-methylphenyl)-2H-benzotriazole mixtures are prepared by alkylating 2-(2-hydroxy-5-methylphenyl)-2H-benzotriazole with a straight chain alkene or with a branched chain alkene of 8 to 30 carbon atoms in the presence of an acidic catalyst at 100°-200° C. The liquid mixtures exhibit outstanding efficacy in protecting organic substrates from light induced deterioration as well as good resistance to loss by volatilization or exudation during the processing of stabilized compositions at elevated temperatures.

Claims

1. A normally liquid or non-crystalline mixture of benzotriazoles, suitable for stabilizing organic materials against light-induced deterioration, which consists essentially of compounds of the formula ##STR11## wherein T₁ is hydrogen or chloro, and

T₂ is a random statistical mixture of at least three isomeric branched secondary alkyl groups each having 8 to 30 carbon atoms and having the formula ##STR12## where E₁ is a straight-chain alkyl of 1 to 14 carbon atoms and E₂ is a straight-chain alkyl of 4 to 15 carbon atoms where the total number of carbon atoms in E₁ plus E₂ is 7 to 29, which mixture is prepared by alkylating a a benzotriazole of the formula ##STR13## where T₁ is hydrogen or chloro, with a straight chain alkene of 8 to 30 carbon atoms in the presence of an acidic catalyst at a temperature of 100°

to 200°

C.

2. A mixture according to claim 1 where T₁ is hydrogen.

3. A mixture according to claim 1 where T₂ is alkyl of 8 to 16 carbon atoms.

4. A mixture according to claim 3 where T₂ is alkyl of 10 to 12 carbon atoms.

9. A stabilized composition which comprises

(a) an organic material, and

(b) an effective amount of a mixture of stabilizers of formula I according to claim 1.

10. A stabilized composition according to claim 9 wherein the organic material (a) is an organic polymer.

11. A stabilized composition according to claim 10 wherein the organic polymer is a polyolefin, a styrene polymer, a polyacrylate, a polyamide, a polyurethane, a halogen containing vinyl polymer, an alkyd resin, a thermoset acrylic resin or an epoxy resin.

12. A stabilized composition according to claim 9 wherein the organic material is in the form of photographic material or part of a photographic element.

5. A normally liquid or non-crystalline mixture of benzotriazoles, suitable for stabilizing organic materials against light induced deterioration, which consists essentially of compounds of the formula ##STR14## wherein R₁ is hydrogen or chloro, and

R₂ is a random statistical mixture of at least three isomeric branched alkyl groups and each having 8 to 30 carbon atoms and having a multiplicity of alkyl branches along the main alkyl chain, which mixture is prepared by

alkylating a benzotriazole of the formula ##STR15## where R₁ is hydrogen or chloro, with a branched chain alkene of 8 to 30 carbon atoms in the presence of an acidic catalyst at a temperature of 100°

to 200°

C.

6. A mixture according to claim 5 wherein R₁ is hydrogen.

7. A mixture according to claim 5 where R₂ is alkyl of 8 to 16 carbon atoms.

8. A mixture according to claim 7 where R₂ is alkyl of 9 to 12 carbon atoms.

13. A stabilized composition which comprises

(a) an organic material, and

(b) an effective amount of a mixture of stabilizers of formula II according to claim 5.

14. A stabilized composition according to claim 13 wherein the organic material (a) is an organic polymer.

15. A stabilized composition according to claim 14 wherein the organic polymer is a polyolefin, a styrene polymer, a polyacrylate, a polyamide, a polyurethane, a halogen containing vinyl polymer, an alkyd resin, a thermoset acrylic resin or an epoxy resin.

16. A stabilized composition according to claim 13 wherein the organic material is in the form of photographic material or part of a photographic element.