Thiocarbamate stabilizers

• US 4,521,320 A
• Filed: 10/21/1983
• Issued: 06/04/1985
• Est. Priority Date: 10/21/1983
• Status: Expired due to Fees

• Current Assignee: CIBA Specialty Chemicals
• Original Assignee: CIBA Vision Corporation (Bayer AG)
• Inventors: Pastor, Stephen D., Spivack, John D.
• Primary Examiner(s): Jiles, Henry R.
• Assistant Examiner(s): WHITTENBAUGH, ROBERT
• Application Number:
  US06/544,295
• Time in Patent Office: 592 Days
• Field of Search: 260/455 A, 524/201, 524/199, 252/47.5, 252/402
• US Class Current: 508/444
• CPC Class Codes: C08K 5/39 Thiocarbamic acids; Derivatives thereof, e.g. dithiocarbamates

Abstract

The title compounds correspond to the formula ##STR1## and are useful as stabilizers for organic polymers and lubricating oils to counteract the degradative effects of heat, light and air.

Claims

1. A compound of the formula ##STR3## wherein R and R₁ are independently hydrogen, alkyl of 1 to 18 carbon atoms, cycloalkyl of 5 to 6 carbon atoms, phenyl, phenyl substituted by alkyl of 1 to 18 carbon atoms, aralkyl of 7 to 9 carbon atoms or said aralkyl substituted by alkyl of 1 to 12 carbon atoms;

n is 1-3, and

when n=1, A is alkyl of 1 to 30 carbon atoms, cycloalkyl of 5 to 6 carbon atoms, phenyl or lower alkyl substituted benzyl;

when n=2, A is alkylene of from 1 to 10 carbon atoms, cycloalkylene of 5 to 6 carbon atoms, lower alkyl-substituted cycloalkylene of 5 to 6 carbon atoms, lower alkylene-substituted cycloalkylene of 5 to 6 carbon atoms, arylene, biphenylene, hydroxy-substituted arylene or polyoxyalkylene with from 2 to 4 carbon atoms in the repeating unit; and

when n=3, A is arylene, biphenylene, hydroxy-substituted arylene or alkanetriyl of from 3 to 6 carbon atoms.

2. The compound of claim 1, wherein R and R₁ are in the ortho position to the hydroxyl group.

3. The compound of claim 2, wherein R and R₁ are alkyl of from 1 to 8 carbon atoms.

4. The compound of claim 3, wherein R and R₁ are tert.butyl.

5. The compound of claim 1, wherein n=1 and A is phenyl or alkyl of 4 to 18 carbon atoms.

6. The compound of claim 1, wherein n=2 and A is alkylene of 4 to 8 carbon atoms, phenylene or C₁ -C₄ alkylene-substituted cyclohexylene.

7. S-(3,5-di-tert-butyl-4-hydroxyphenyl)-N-phenylthiocarbamate according to claim 5.

8. S-(3-tert-butyl-5-methyl-4-hydroxyphenyl)-N-octadecylthiocarbamate according to claim 5.

9. S-(3,5-di-tert-butyl-4-hydroxyphenyl)-N-butylthiocarbamate according to claim 5.

10. S,S'"'"'-bis(3,5-di-tert-butyl-4-hydroxyphenyl)-N,N'"'"'-1,6-hexanediyl-bis(thiocarbamate) according to claim 6.

11. S-(3,5-di-tert-butyl-4-hydroxyphenyl)-N-(n-octadecyl)thiocarbamate according to claim 5.

12. 1,1,5,5-tetramethyl-1'"'"',3-bis[S-(3,5-di-tert-butyl-4-hydroxyphenyl)thiocarbamyl]cyclohexane according to claim 1.

13. A composition of matter comprising an organic material selected from the group consisting of polyolefins, polystyrene, rubbers, polyesters and lubricating oils subject to oxidative, thermal and actinic degradation stabilized with an effective stabilizing amount of a compound of claim 1.

14. The composition of claim 13, wherein the organic material is a synthetic polymer.

15. The composition of claim 14, wherein said polymer is selected from the group consisting of impact polystyrene, acrylonitrile/butadiene/styrene, styrene/butadiene rubber, polyesters and poly-alpha-olefins.

16. A method for stabilizing an organic material selected from the group consisting of polyolefins, polystyrene, rubbers, polyesters and lubricating oils against oxidative, thermal and actinic degradation which comprises incorporating into said organic material an effective stabilizing amount of a compound of claim 1.