Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters
Patent
1995-06-20
1997-12-09
Killos, Paul J.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acid esters
C07C 6976
Patent
active
056962819
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/EP93/03502 Dec. 10, 1993.
Sterically hindered phenols are known stabilisers for organic materials that are susceptible to thermal, oxidalive and/or actinic degradation. Thus, for example, U.S. Pat. No. 4,032,562 discloses phenol stabilisers that may contain up to 3 to 8 alkylene oxide units and are terminated with --OH, methoxy or ethoxy. U.S. Pat. No. 4,713,475 and U.S. Pat. No. 4,228,297 disclose phenol-substituted propionates containing 3 to 50 carbon atoms in the ester radicals. U.S. Pat. No. 4,477,638 teaches the use of different phenol-substituted propionic acid derivatives as chain-terminators for the synthesis of polyvinyl chloride. BE patent 645 505 discloses stearyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate as component of a stabiliser mixture together with phosphites and thioesters. Analogous compounds are disclosed in BE patent 636 254 and GB 1 290 848 the compound being used in the Belgian patent as component of a stabiliser mixture together with a selection of many other components. U.S. Pat. No. 3,247,240 discloses a process for the preparation of carbonyl compounds that contain hindered phenol groups.
Some novel phenolic carboxylic acid esters have now been found that have particularly good stabiliser properties.
Specifically, the invention relates to compounds of formula I ##STR1## wherein R.sub.1 is C.sub.1 -C.sub.18 alkyl, C.sub.5 -C.sub.12 cycloalkyl, phenyl, benzyl, .alpha.-methylbenzyl or .alpha.,.alpha.-dimethylbenzyl,
R.sub.1 and R.sub.2 defined as C.sub.1 -C.sub.18 alkyl are a branched or unbranched radical. Branched C.sub.1 -C.sub.18 alkyl will be understood as meaning radicals containing secondary carbon atoms as well as those containing tertiary carbon atoms. Typical examples of branched and unbranched C.sub.1 -C.sub.18 alkyl radicals are methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, 2-ethylbutyl, n-pentyl, isopentyl, 1-methylpentyl, 1,3-dimethylbutyl, n-hexyl, 1-methylhexyl, n-heptyl, isoheptyl, 1,1,3,3-tetramethylbutyl, 1-methylheptyl, 3-methylheptyl, n-octyl, 2-ethylhexyl, 1,1,3-trimethylhexyl, 1,1,3,3-tetramethylpentyl, nonyl, decyl, undecyl, 1-methylundecyl, dodecyl, 1,1,3,3,5,5-hexamethylhexyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl or octadecyl, preferably methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl. Methyl and tert-butyl are particularly preferred.
R.sub.1 and R defined as C.sub.5 -C.sub.12 cycloalkyl are cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cycloundecyl or cyclododecyl. Cyclopentyl and cyclohexyl are preferred. Cyclohexyl is particularly preferred.
R.sub.3 defined as C.sub.4 -C.sub.50 alkyl is a branched or linear radical. Branched C.sub.4 -C.sub.50 alkyl will be understood as meaning radicals containing secondary carbon atoms as well as those containing tertiary carbon atoms. Typical examples of branched and unbranched C.sub.4 -C.sub.50 alkyl radicals are n-butyl, sec-butyl, isobutyl, tert-butyl, 2-ethylbutyl, n-pentyl, isopentyl, 1-methylpentyl, 1,3-dimethylbutyl, n-hexyl, 1-methylhexyl, n-heptyl, isoheptyl, 1,1,3,3-tetramethylbutyl, 1-methylheptyl, 3-methylheptyl, n-octyl, 2-ethylhexyl, 1,1,3-trimethylhexyl, 1,1,3,3-tetramethylpentyl, nonyl, decyl, undecyl, 1-methylundecyl, dodecyl, 1,1,3,3,5,5-hexamethylhexyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, eicosyl, docosyl, tetracosyl, pentacosyl, octacosyl, triacontyl, dotriacontyl, tetracontyl or pentacontyl.
R.sub.3 is preferably unbranched alkyl, more particularly nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl and pentadecyl. R.sub.3 is typically C.sub.8 -C.sub.40 alkyl, conveniently C.sub.10 -C.sub.40 alkyl or C.sub.10 -C.sub.18 alkyl, preferably C.sub.12 -C.sub.18 alkyl.
C.sub.m H.sub.2m is linear or branched alkyl containing not more than 3 carbon atoms and is typically methylene, ethylene, propylene, ethylidene or propylidene, preferably methylene and ethylene. Ethylene is most preferred.
The compounds of formula I are typically p
REFERENCES:
patent: 3247240 (1966-04-01), Meier et al.
patent: 4032562 (1977-06-01), Dexter et al.
patent: 4228297 (1980-10-01), Haeberli et al.
patent: 4477638 (1984-10-01), Reid
patent: 4713475 (1987-12-01), Spivack et al.
Chem. Abstract 63:13506b.
Chem. Abstract 62:2887b.
Ciba Specialty Chemicals Corporation
Hall Luther A. R.
Killos Paul J.
Kovaleski Michele A.
Malia Victoria M.
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