2-(2-Hydroxyphenyl)-benztriazoles, their use as UV-absorbers and their preparation

• US 4,853,471 A
• Filed: 11/12/1987
• Issued: 08/01/1989
• Est. Priority Date: 01/23/1981
• Status: Expired due to Term

• Current Assignee: CIBA Specialty Chemicals
• Original Assignee: Ciba-Geigy Corporation (Novartis Ag)
• Inventors: Slongo, Mario, Rody, Jean
• Primary Examiner(s): Daus, Donald G.
• Assistant Examiner(s): NOT, DEFINED
• Application Number:
  US07/122,554
• Time in Patent Office: 628 Days
• Field of Search: 548/259, 548/260, 548/261, 526/259, 524/91
• US Class Current: 548/261
• CPC Class Codes: C07D 249/20 with aryl radicals directly attached in position 2
• CPC Class Codes: C08K 5/3475 condensed with carbocyclic rings
• CPC Class Codes: C09D 7/48 Stabilisers against degradation by oxygen, light or heat
• CPC Class Codes: G03C 1/8155 Organic compounds therefor

Abstract

The novel UV-absorbers are compounds of the formula ##STR1## in which R¹ is, for example, hydrogen, n is one of the numbers 1 or 2 and R² is an appropriate monovalent or divalent radical, for example --OH or --O--CH₂ CH₂ --O--. The UV-absorbers are used in particular for stabilising and improving lacquers and photographic material.

Claims

1. A compound of the formula I ##STR40## in which R¹ is H, Cl or straight-chain or branched C₁ -C₄ alkyl and n is one of the numbers 1 or 2, in which,

(a) when n=1, R² is Cl or --OR³, and

(b) when n=2, R² is --O--R⁹ --O--, R³ is H, straight-chain or branched C₁ -C₁₈ alkyl which is unsubstituted or substituted by 1 to 3 OH groups or straight-chain or branched C₃ -C₁₈ alkyl which is interrupted by --O-- or --S-- and which can be unsubstituted or substituted by OH, C₅ -C₁₂ cycloalkyl which is unsubstituted or substituted by OH, straight-chain or branched C₂ -C₁₈ alkenyl which is unsubstituted or substituted by OH, C₇ -C₁₅ aralkyl, or ##STR41## R⁹ is C₂ -C₈ alkylene, C₄ -C₈ alkenylene, cyclohexylene, straight-chain or branched C₄ -C₁₀ alkylene which is interrupted by --O--, and R¹¹ is straight-chain or branched C₂ -C₈ alkylene, straight-chain or branched C₄ -C₁₀ alkylene which is interrupted by --O--, cycloalkylene, arylene, ##STR42##

2. A compound according to claim 1 of the formula I in which R¹ is H or Cl, n is the number 1 and R² is --OR³, R³ is straight-chain or branched C₄ -C₁₂ alkyl, straight-chain or branched C₃ -C₁₀ alkyl which is interrupted by O or cyclohexyl.

3. A compound according to claim 1 of the formula I in which R¹ is H or Cl, n is the number 2 and R² is --O--R⁹ --O--, R⁹ is C₂ -C₆ alkylene, straight-chain or branched C₄ -C₁₀ alkylene which is interrupted by --O--, ##STR43## and R¹¹ is C₂ -C₆ alkylene or straight-chain or branched C₄ -C₁₀ alkylene which is interrupted by --O--.

4. A compound according to claim 1 which is 2-[2-hydroxy-3-tert.-butyl-5-(2-carbo-n-octyloxythyl)-pheny]-benztriazole or 2-{2-hydroxy-3-tert.-butyl-5-[2-carbo-(2-ethylhexyl)-oxyethyl]-phenyl}-benztriazole or 2-[2-hydroxy-3-tert.-butyl-5-(2-carbo-n-octyloxyethyl)-phenyl]-5-chlorobenztriazole or 2-{2-hydroxy-3-tert.-butyl-5-[2-carbo-(2-ethylhexyl)-oxyethyl]-phenyl}-5-chlorobenztriazole or the compound of the formula ##STR44##

5. A mixture of 2-[2-hydroxy-3-tert.-butyl-5(2-carbo-n-octyloxyethyl)-phenyl]-5-chlorobenztriazole and 2-{2-hydroxy-3-tert.-butyl-5-[2-carbo-(2-ethylhexyl)-oxyethyl]-phenyl}-5-chlorobenztriazole in a ratio by weight of 1:

1.