Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Processes of preparing a desired or intentional composition...
Patent
1993-08-09
1995-06-13
Kumar, Shailendra
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Processes of preparing a desired or intentional composition...
252475, 252 515A, 252402, 252403, 106186, 524169, 524219, 530427, 564 92, 564 99, 564182, 564219, 564153, 564156, C08K 520, C07C23365
Patent
active
054243491
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/U.S. Ser. No. 92/01559 filed Feb. 26, 1992.
FIELD OF INVENTION
This invention relates to novel amides having utility as antioxidants.
BACKGROUND
Many organic materials, such as polymers, fuels, and lubricants, are normally susceptible to oxidative deterioration and tend to suffer severe degradation and/or discoloration during processing and/or later use unless they are stabilized.
The compounds which have previously been proposed for use in stabilizing these materials have frequently been phenolic compounds, and some such compounds have been very successfully employed as antioxidants for some of the normally oxidizable materials. However, no single compound could be the best possible antioxidant for each of the variety of organic materials which are normally susceptible to oxidative deterioration, since: stability are not necessarily those which have the most suitable melting points, the least tendency to degrade to highly-colored compounds, and the greatest ability to stabilize organic materials during processing, than others (e.g., fuels and lubricants) of tolerating the substantial discoloration that occurs when many phenolic compounds are subjected to processing conditions, stability that they are unsuitable for use in organic materials for which high processing temperatures and/or long-term stabilization are required, and drawback to their use in materials which must be processed at low or moderate temperatures.
Thus, it is necessary to have different antioxidants to serve the different needs of the various organic materials which require stabilization.
Because of the need for these different antioxidants for different organic materials, it would be desirable to be able to find a class of antioxidants which could be derived from a common intermediate or a common genus of intermediates that could be easily modified so as to provide the different antioxidant properties required in the variety of specific market needs.
As disclosed in U.S. Pat. Nos. 3,780,103 (Knell), 3,808,273 (Burdet et al.), 3,927,091 (Huber-Emden et al.), 3,996,194 (Gencarelli et al.), 4,098,760 (Cornell), 4,100,191 (Fischer et al.), and 4,132,702 (Schmidt et al.) and Netherlands Patent Application 7905000 (Cincinnati Milacron Chemicals), it is known that some amides containing substituted hydroxyphenyl groups have been found to be useful as stabilizers for some organic materials which are normally susceptible to oxidative deterioration.
N,N-bis(3,5-di-t-butyl-4-hydroxybenzyl)acetamide is disclosed by G. A. Nikiforov et al. in Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 12, pp. 2765-2770, 1989.
SUMMARY OF INVENTION
The invention resides in (1) tertiary amides corresponding to the formula: ##STR2## wherein R is a mono-, di-, or trivalent aromatic or saturated aliphatic hydrocarbon group containing 1-20 carbons; n is an integer of 1-3 which is equal to the valence of R; R' is phenyl, benzyl, or C.sub.1 -C.sub.6 alkyl; m is an integer of 1-3; R" is a C.sub.1 -C.sub.4 alkylene group; Z and Z' are independently selected from hydrogen and alkyl; and Q is carbonyl or sulfonyl and (2) the use of the tertiary amides as antioxidants for organic materials which are normally susceptible to oxidative deterioration.
DETAILED DESCRIPTION
The novel tertiary amides of the invention are amides containing alkyl-substituted hydroxyphenyl groups which are separated from the amido nitrogens by a linking chain of at least two carbons. This type of linkage is an important feature of the compounds, since it provides lower volatility and higher thermal stability than a linkage constituted by a single carbon and thus makes the compounds superior to the corresponding compounds containing the shorter linkage, e.g., the compounds of Nikiforov et al.
As indicated by the formula, the p-alkyl substitutent represented by CZZ'R" may have a branched chain when R" is a branched alkylene group and/or at least one of Z and Z' is alkyl (usually an alkyl of only 1-4 carbons). However, it is generally preferred for tha
REFERENCES:
patent: 4098760 (1978-07-01), Cornell
patent: 4100191 (1978-07-01), Fischer et al.
patent: 5103054 (1992-04-01), Gatto
patent: 5130484 (1992-07-01), Gatto
Albemarle Corporation
Hammond Richard J.
Hogan Patricia J.
Kumar Shailendra
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