Claims
- 1. A polymeric composition useful as an antioxidant which comprises a polymer having a molecular weight ranging from about 300 to about 3,000 and consists of the polymeric reaction product of (a) an N-aryl or N-alkaryl substituted diphenyldiamine of the formula: ##STR3## wherein each R may be the same or different and is a radical selected from the group consisting of hydrogen and alkyls having from 1 to 8 carbon atoms; and (b) at least one diene selected from the group consisting (1) conjugated dienes consisting of 1,3-butadiene, isoprene, chloroprene, 2-ethyl-1,3-butadiene, 2,3-dimethyl-1,3-butadiene and piperylene; and (2) nonconjugated dienes consisting of 1,4-pentadiene, 1,4-hexadiene, ethylidene norbornene, 1,4-diisopropenylbenzene, 1,3-diisopropenylbenzene, 1,4-di-.alpha.-ethylvinylbenzene, 1,3 -di-.alpha.-ethylvinylbenzene, 1-isopropenyl-4-.alpha.-ethylvinylbenzene, 1-isopropenyl-3-.alpha.-ethylvinylbenzene, 1-.alpha.-ethylvinyl-4-.alpha.'-isopropylvinylbenzene, 1-.alpha.-ethylvinyl-3-.alpha.'-isopropylvinylbenzene, 1,4-di-.alpha.isopropylvinylbenzene, 1,3-di-.alpha.-isopropylvinylbenzene limonene vinylcyclohexene, cyclooctadiene, dicyclopentadiene 1,5,9-cyclododecatriene and mixtures thereof; and wherein the molar ratio of polymer units derived from diphenyldiamine to diene ranges from about 2:1 to 1:2.
- 2. The polymeric composition of claim 1 wherein R is selected from the group consisting of hydrogen and alkyls having from about 1 to about 3 carbon atoms and the diene is selected from the group consisting of 1,4-diisopropenylbenzene, 1,3-diisopropenylbenzene and isoprene.
- 3. The polymeric composition of claim 1 having an average molecular weight of from about 500 to about 3000.
- 4. The polymeric composition of claim 1 wherein said diphenyldiamine and said diene are reacted in the presence of an acid catalyst.
- 5. The polymeric composition of claim 1 wherein said acid catalyst is a Bronsted acid or Lewis acid.
- 6. The polymeric composition of claim 5 wherein said acid catalyst is H.sub.2 SO.sub.4, HCl, H.sub.3 PO.sub.4, HClO.sub.4, BF.sub.3, BCl.sub.3, AlCl.sub.3, AlBr.sub.3, SnCl.sub.4, ZnCl.sub.2, SbCl.sub.3 and etherates of said acid catalysts.
- 7. The polymeric composition of claim 6 wherein said acid catalyst is BF3 and BF3 etherate.
- 8. A composition comprising (1) a diene containing polymer and (2) a polymeric antioxidant having a molecular weight ranging from about 300 to 3,000 and consists of the polymeric reaction product of
- (a) an N-aryl substituted or N-alkaryl substituted diphenyldiamine of the formula: ##STR4## wherein each R may be the same or different and is a radical selected from the group consisting of hydrogen and alkyls having from 1 to 8 carbon atoms;
- (b) at least one diene selected from the group consisting of (1) conjugated dienes consisting of 1,3-butadiene, isoprene, chloroprene, 2-ethyl-1,3-butadiene, 2,3-dimethyl-1,3-butadiene and piperylene; and (2) nonconjugated dienes consisting of 1,4-pentadiene, 1,4-hexadiene, ethylidene norbornene, 1,4-diisopropenylbenzene, 1,3-diisopropenylbenzene, 1,4-di-.alpha.-ethylvinylbenzene, 1,3-di-.alpha.-ethylvinylbenzene, 1-isopropenyl-4-.alpha.-ethylvinylbenzene, 1-isopropenyl-3-.alpha.-ethylvinylbenzene, 1-.alpha.-ethylvinyl-4-.alpha.'-isopropylvinylbenzene, 1-.alpha.-ethylvinyl-3-.alpha.'-isopropylvinylbenzene, 1,4-di-.alpha.-isopropylvinylbenzene, 1,3-di-.alpha.-isopropylvinylbenzene, limonene, vinylcyclohexene, cyclooctadiene, dicyclopentadiene 1,5,9-cyclooctatriene and mixtures thereof; and wherein the molar ratio of polymer units derived from diphenyldiamine to diene ranges from about 2:1 to 1:2.
- 9. The composition of claim 8 wherein said diene containing polymer is selected from the group comprising natural rubber, polyisoprene, polybutadiene, polychloroprene, copolymers of isoprene and butadiene, copolymers of styrene and butadiene, copolymers of acrylonitrile and butadiene, copolymers of acrylonitrile and isoprene and blends thereof.
- 10. The composition of claim 9 wherein said polymeric antioxidant is present in an amount ranging from about 0.1 to 10 parts per hundred parts of diene polymer.
- 11. The composition of claim 9 wherein said polymeric antioxidant is present in an amount ranging from about 1 to about 7 parts per hundred parts of diene polymer.
Parent Case Info
This is a continuation of application Ser. No. 08/697,122, filed on Aug. 20, 1996, now abandoned, which in turn is a continuation of application Ser. No. 08/303,920, filed on Sep. 9, 1994, now abandoned.
US Referenced Citations (2)
Number |
Name |
Date |
Kind |
5049625 |
Tazuma et al. |
Sep 1991 |
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5280071 |
Sturm et al. |
Jan 1994 |
|
Non-Patent Literature Citations (2)
Entry |
Miller et al., "Persistent Antioxidants", (1989) CA #112:140956 (ABS only). |
Giurnica et al., "Oxidation in Presence Of Amines," (1982) CA #97:24977 (ABS only). |
Continuations (2)
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Number |
Date |
Country |
Parent |
697122 |
Aug 1996 |
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Parent |
303920 |
Sep 1994 |
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