Tri- and Tetra-(substituted hydroxyphenylthio) alkane and cycloalkane stabilizers and stabilized compositions

• US 4,560,799 A
• Filed: 02/03/1984
• Issued: 12/24/1985
• Est. Priority Date: 02/03/1984
• Status: Expired due to Fees

• Current Assignee: Ciba-Geigy Corporation (Novartis Ag)
• Original Assignee: Ciba-Geigy Corporation (Novartis Ag)
• Inventors: Pastor, Stephen D., Spivack, John D.
• Primary Examiner(s): Daus, Donald G.
• Assistant Examiner(s): Shen, Cecilia
• Application Number:
  US06/576,978
• Time in Patent Office: 690 Days
• Field of Search: 568/47, 524/331
• US Class Current: 568/47
• CPC Class Codes: C07C 323/00 Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
• CPC Class Codes: C08K 5/375 containing six-membered aromatic rings C08K5/3725 takes precedence
• CPC Class Codes: C09K 15/14 containing a phenol or quinone moiety
• CPC Class Codes: C10M 135/30 containing hydroxy groups; Derivatives thereof
• CPC Class Codes: C10M 2219/087 containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
• CPC Class Codes: C10M 2219/088 Neutral salts
• CPC Class Codes: C10M 2219/089 Overbased salts

Abstract

Organic materials are stabilized against thermal, oxidative and photo-degradation by incorporating therein an effective amount of a compound of formula I ##STR1## wherein T₁ T₂ independently are alkyl, cycloalkyl, phenyl, aralkyl, T₂ may also be hydrogen, T is alkyl, phenyl or substituted hydroxyphenyl, E is a direct bond, alkylene, cycloalkylene, phenylene or --CH₂ CH(ST)CH₂ --, T₃ and T₄ are independently hydrogen, alkyl or cycloalkyl; or together are alkylene, T₅ is hydrogen, alkyl or phenyl, n is 1 or 2, t is 0 or 1, and t is 2-n. Polyolefins, ABS resins, natural and synthetic rubbers and polyesters are particularly well stabilized by the compounds of formula I.

Claims

1. A compound of formula I ##STR7## wherein T₁ and T₂ are independently alkyl of 1 to 12 carbon atoms, cycloalkyl of 5 to 6 carbon atoms, phenyl, phenyl substituted by alkyl of 1 to 12 carbon atoms, phenylalkyl of 7 to 9 carbon atoms or said phenylalkyl substituted by alkyl of 1 to 12 carbon atoms,

T₂ may also be hydrogen,

T is alkyl of 1 to 24 carbon atoms, phenyl, phenyl substituted by alkyl of 1 to 12 carbon atoms, or the group ##STR8## E is a direct bond, alkylene of 1 to 11 carbon atoms, cycloalkylene of 5 to 6 carbon atoms or phenylene, or is the group ##STR9## T₃ and T₄ are independently hydrogen, alkyl of 1 to 30 carbon atoms, said alkyl substituted by phenyl or by phenyl substituted by alkyl of 1 to 12 carbon atoms, cycloalkyl of 5 to 6 carbon atoms, or

T₃ and T₄ together are straight- or branched-chain alkylene of 3 to 7 carbon atoms when E is methylene,

T₅ is hydrogen, alkyl of 1 to 4 carbon atoms or phenyl,

n is 1 or 2, t is 0 or 1, and t is 2-n.

2. A compound according to claim 1 where T₂ is in the ortho position to the hydroxy group.

3. A compound according to claim 2 wherein T₁ and T₂ are independently alkyl of 1 to 8 carbon atoms.

4. A compound according to claim 3 wherein T₁ is methyl or tert-butyl and T₂ is tert-butyl.

5. A compound according to claim 4 wherein T₁ is tert-butyl.

6. A compound according to claim 1 wherein T is alkyl of 7 to 18 carbon atoms or is the group ##STR10## where T₁ and T₂ are defined in claim 1.

7. A compound according to claim 1 wherein E is a direct bond, alkylene of 1 to 6 carbon atoms or the group ##STR11## where T is defined in claim 1.

8. A compound according to claim 1 wherein T₃ and T₄ are independently hydrogen or alkyl of 1 to 4 carbon atoms;

or T₃ and T₄ together are trimethylene or 2,2-dimethylpropan-1,3-diyl when E is methylene.

9. A compound according to claim 1 wherein T₅ is hydrogen or methyl.

10. A compound according to claim 1 which is 1,1,2,2-tetrakis(3,5-di-tert-butyl-4-hydroxyphenylthio)ethane.

11. A compound according to claim 1 which is 1,1,5,5-tetrakis(3,5-di-tert-butyl-4-hydroxyphenylthio)pentane.

12. A compound according to claim 1 which is 1,1,3-tris(3,5-di-tert-butyl-4-hydroxyphenylthio)butane.

13. A compound according to claim 1 which is 1,1-bis(3,5-di-tert-butyl-4-hydroxyphenylthio)-3-(n-dodecylthio)butane.

14. A compound according to claim 1 which is 1,1,3-tris(3-tert-butyl-5-tert-octyl-4-hydroxyphenylthio)-3,5,5-trimethylcyclohexane.