Antioxidants containing phenol groups and aromatic amine groups

Details Antioxidants containing phenol groups and aromatic amine groups Antioxidants containing phenol groups and aromatic amine groups

1998-04-27

2000-02-22

Hoke, Veronica P.

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

Processes of preparing a desired or intentional composition...

524199, 524217, 524239, 524240, 558275, 560 11, 560 12, 560 15, 560 16, 560 29, 564 50, 564162, 564165, 564182, C07C 6996, C07C32100, C07C31500, C08K 541

Patent

active

060281316

DESCRIPTION:

BRIEF SUMMARY
The invention relates to compounds of the formula I described below, to compositions comprising these compounds, and to their use for stabilizing organic materials.
The stabilizers which have hitherto been incorporated into the molecular structure of the substrate to be stabilized are, for example, acrylates of the Ph--NH--C.sub.6 H.sub.4 --NH--CO--CH.dbd.CH.sub.2 type. The double bond participates in the polymerization or crosslinking of the substrate (U.S. Pat. No. 3,975,414, U.S. Pat. No. 4,743,657; D. K. Parker and G. O. Schulz, Rubber Chemistry and Technology 62,732; D. E. Miller et al., Rubber World 1989, 200(5), 13-16 and 18-23; and CA 112:140956x). The advantage of such stabilizers which can be incorporated is that losses due to leaching-out or diffusion can be avoided. Stabilizers are already known, in particular for rubber, which conform to the formula ##STR5## where Z is O or NH, X is (C.sub.2 H.sub.4 OCH.sub.2 OC.sub.2 H.sub.4 SS).sub.m C.sub.2 H.sub.4 OCH.sub.2 OC.sub.2 H.sub.4, R is t-C.sub.4 -C.sub.8 alkyl, m is from 4 to 24 and R.sub.3 is H or C.sub.1 -C.sub.18 alkyl (U.S. Pat. No. 4,727,105).
The invention relates to compounds of the formula I ##STR6## in which R is C.sub.1 -C.sub.18 alkyl, C.sub.5 -C.sub.8 cycloalkyl, C.sub.7 -C.sub.9 phenylalkyl, --CH.sub.2 --A--R.sub.2 or a group of the formula II, ##STR7## R.sub.1 is C.sub.1 -C.sub.18 alkyl, C.sub.5 -C.sub.8 cycloalkyl, C.sub.7 -C.sub.9 phenylalkyl or a group of the formula (II), preferably methyl or tert-butyl, group of the formula III, ##STR8## preferably C.sub.8 -C.sub.12 alkyl, R.sub.3 is hydrogen, C.sub.5 -C.sub.8 cycloalkyl or C.sub.1 -C.sub.12 alkyl, preferably hydrogen, 2-propyl, 2-(4-methylpentyl), 2-(5-methylpentyl), 2-octyl, cyclohexyl or 3-(5-methylheptyl), in particular H, -C.sub.9 phenylalkyl or a group of the formula II or IV, ##STR9## preferably methyl or t-butyl, A is S or SO, preferably SO, preferably a direct bond or --CH.sub.2 --, beta-naphthyl, preferably phenyl or alpha- or beta-naphthyl, the formula II chemically incorporated into certain substrates.
Preference is given to compounds of the formula I described above in which a group of the formula II, formula II, formula II or IV,
Particular preference is given to compounds of the formula I described above in which formula II, here are preferably methyl or tert-butyl).
A is particularly preferably SO.
Preference is furthermore given to compounds of the formula I in which R is --CH.sub.2 --A--R.sub.2, R.sub.1 is C.sub.1 -C.sub.18 alkyl, C.sub.5 -C.sub.8 cycloalkyl or C.sub.7 -C.sub.9 phenylalkyl and R.sub.4 is a group of the formula IV; or in which R is a group of the formula II and R.sub.1 and R.sub.4, independently of one another, are C.sub.1 -C.sub.18 alkyl, C.sub.5 -C.sub.8 cycloalkyl or C.sub.7 -C.sub.9 phenylalkyl; or in which R.sub.4 is a group of the formula II and R and R.sub.1, independently of one another, are C.sub.1 -C.sub.18 alkyl, C.sub.5 -C.sub.8 cycloalkyl or C.sub.7 -C.sub.9 phenylalkyl.
If the compounds of the formula I contain two or three groups of the formula ii or IV, the groups E in the formula II are preferably identical to one another.
Depending on the stated number of carbon atoms, alkyl is, for example, methyl, ethyl, n-propyl, isopropyl, n-, i-, sec- or t-butyl, pentyl, hexyl, heptyl, octyl, 2-ethylhexyl, i-octyl, decyl, nonyl, undecyl, dodecyl, tridecyl, quatrodecyl, quindecyl, sedecyl, heptadecyl or octadecyl.
C.sub.5 -C.sub.8 Cycloalkyl is, for example, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl.
C.sub.7 -C.sub.9 Phenylalkyl is, for example, benzyl, 1- or 2-phenylethyl, 3-phenylpropyl, .alpha.,.alpha.-dimethylbenzyl or 2-phenylisopropyl, preferably benzyl.
The compounds of the formula I are suitable for stabilizing organic material, in particular polymers, specifically vulcanizates made from natural and/or synthetic rubber. As a consequence of their active groups, the compounds are effective as antioxidants both when incorporated and in free form. Complete incorporation is not necessarily desired. An incorporation rate of aro

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