Diphenylamine derivatives and degradation inhibitors for rubber polymers

• US 4,298,522 A
• Filed: 06/19/1980
• Issued: 11/03/1981
• Est. Priority Date: 06/21/1979
• Status: Expired due to Term

• Current Assignee: Nippon Zeon Co., Ltd. (BASF SE)
• Original Assignee: Nippon Zeon Co., Ltd. (BASF SE)
• Inventors: Tamura, Mitsuhiro, Sakurai, Hiroshi, Ohishi, Tetsuo
• Primary Examiner(s): Hoke, V. P.
• Application Number:
  US06/160,855
• Time in Patent Office: 502 Days
• Field of Search: 564/92, 564/95, 564/433, 564/434, 260/45.9 QB, 526/292, 526/310, 526/312, 526/288
• US Class Current: 524/169
• CPC Class Codes: C08K 5/18 with aromatically bound amino groups
• CPC Class Codes: C08K 5/42 Sulfonic acids; Derivatives thereof
• CPC Class Codes: C08L 21/00 Compositions of unspecified rubbers

Abstract

A diphenylamine derivative of the general formula ##STR1## wherein R represents a hydrogen atom or a methyl group, R₁ and R₂, independently from each other, represent a hydrogen atom, a chlorine atom, a bromine atom, or a hydrocarbon radical having 1 to 12 carbon atoms, and A represents ##STR2## and a degradation inhibitor for rubbery polymers comprising the aforesaid diphenylamine derivative as an active ingredient.

Claims

1. A diphenylamine derivative which is capable of inhibiting degradation of reactive rubbery polymers, said derivative being of the general formula ##STR11## wherein R represents a hydrogen atom or a methyl group, R₁ and R₂, independently from each other, represent a hydrogen atom, a chlorine atom, a bromine atom, or a hydrocarbon radical having 1 to 12 carbon atoms, and A represents ##STR12## --SO₂ --NH--, or --CH₂ --SO₂ --NH--.

2. The diphenylamine derivative of claim 1 wherein A represents ##STR13##

3. The diphenylamine derivative of claim 1 wherein A represents ##STR14##

4. The diphenylamine derivative of claim 1 wherein A represents --SO₂ --NH--.

5. The diphenylamine derivative of claim 1 wherein A represents --CH₂ --SO₂ --NH--.

6. The diphenylamine derivative of claim 1 which is 4-anilino-N-(4-vinylbenzyl) aniline.

7. The diphenylamine derivative of claim 1 which is 4-anilinophenyl-4-vinylbenzyl ether.

8. The diphenylamine derivative of claim 1 which is N-(4-anilino)phenyl-vinylsulfonamide.

9. The diphenylamine derivative of claim 1 which is N-(4-anilino)-phenyl isopropenyl sulfonamide.

10. A diene-type rubbery polymer composition comprising 100 parts by weight of a diene-type rubbery polymer and 0.01 to 10 parts by weight of the diphenylamine derivative of claim 1 as a degradation inhibitor.

11. The diene-type rubbery polymer composition according to claim 10 wherein said dephenylamine derivative is selected from groups consisting of 4-anilino-N-(4-vinylbenzyl) aniline, 4-anilinophenyl-4-vinylbenzyl ether, N-(4-anilino)phenyl-vinylsulfonamide and N-(4-anilino)-phenyl isopropenyl sulfonamide.

12. A diene-type rubbery polymer composition in which the diphenylamine derivative of claim 1 as a degradation inhibitor is chemically bound to a diene-type rubbery polymer in the form of a segmeric unit of the general formula ##STR15## wherein R, R₁, R₂ and A are as defined.