Tetramethylpiperidine-containing copolymers

Details Tetramethylpiperidine-containing copolymers Tetramethylpiperidine-containing copolymers

1998-05-29

1999-10-26

Lipman, Bernard

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

Synthetic resins

Processes of preparing a desired or intentional composition...

524 99, 524102, 526258, C08K 53435

Patent

active

059730404

DESCRIPTION:

BRIEF SUMMARY
The present invention relates to tetramethylpiperidine-containing copolymers comprising formula I ##STR2## and II) 0-99 mol % of identical or different monomer units of the general formula II ##STR3## where X is oxygen, sulfur or NR.sup.6, CONR.sup.8 R.sup.9 or CN, every third chain carbon being replaceable by oxygen or NR.sup.6, or is C.sub.3 -C.sub.8 -cycloalkyl, phenyl or ##STR4## R.sup.5 is hydrogen, methyl, ethyl or propyl, R.sup.6 is hydrogen or C.sub.1 -C.sub.8 -alkyl, C.sub.3 -C.sub.5 -alkenyl or phenyl which can be substituted by 1-3 C.sub.1 -C.sub.4 -alkyls, C.sub.1 -C.sub.4 -alkoxys, C.sub.1 -C.sub.4 -alkoxycarbonyls, halogens, hydroxyls, phenoxys, phenyls, tolyls or xylyls, -C.sub.8 -cycloalkyl or phenyl which can be substituted by 1-3 C.sub.1 -C.sub.4 -alkyls, C.sub.1 -C.sub.4 -alkoxys, C.sub.1 -C.sub.4 -alkoxycarbonyls, halogens, hydroxyls, phenoxys, phenyls, tolyls or xylyls, ##STR5## m and n are 0 or 1 and r is 0-100.
The invention additionally relates to processes for preparing the compounds, to the use of the copolymers as stabilizers and to organic material comprising the copolymers which is stabilized against the action of light, oxygen and heat.
Organic material, especially plastics and coating materials, is destroyed very rapidly by light, oxygen and heat, as is manifested for example in yellowing, discoloration, embrittlement or cracking. The intention of stabilizers is to prevent this destruction and to achieve extensive protection of the organic material against these damaging effects.
Among stabilizers, compounds with hindered amine units, such as the tetramethylpiperidine structure, have proven particularly suitable. Particularly advantageous tetramethylpiperidine compounds, in turn, are those having two or more piperidine radicals, for example dimeric or polymeric structures, since such compounds are diffused out of the stabilized organic material only with difficulty and therefore exhibit a particularly long-term protective effect.
U.S. Pat. No. 4,413,096 describes .alpha.-olefin copolymers with side chains which comprise tetraalkylpiperidine radicals, which radicals can be substituted on the nitrogen by hydrogen, oxyl, C.sub.1 -C.sub.8 -alkyl, C.sub.3 -C.sub.8 -alkenyl, C.sub.3 -C.sub.6 -alkynyl, C.sub.7 -C.sub.8 -aralkyl, --CH.sub.2 CN, C.sub.2 -C.sub.21 -alkoxyalkyl, aliphatic C.sub.1 -C.sub.4 -acyl, --CH.sub.2 COOR or --COOR in which R can again be various organic radicals.
A frequent point of dissatisfaction in such prior art compositions is the low compatibility with plastics, the duration of the protective effect, the inherent color of the compounds, their low resistance to decomposition when incorporated at elevated temperatures and, in particular, their sensitivity to acidic, sulfur- and halogen-containing solids, liquids and gases.
It is an object of the present invention to provide stabilizers for organic material which provide more effective protection against light, oxygen and heat, especially in combination with improved protection against acidic liquids and gases.
We have found that this object is achieved by the tetramethylpiperidine-containing copolymers described at the outset.
A preferred bridge member X is oxygen.
A preferred radical R.sup.1 is COOR.sup.7.
R.sup.2 is preferably hydrogen or COOR.sup.7.
R.sup.3 and R.sup.5 are preferably hydrogen or methyl.
R.sup.4 is preferably hydrogen, methyl, phenyl or ##STR6##
The latter two radicals R.sup.4 are particularly preferred when m and n are 1 and X is oxygen or NR.sup.6.
R.sup.6 is preferably hydrogen, methyl or ethyl.
R.sup.7 is preferably C.sub.1 -C.sub.4 -alkyl, especially ethyl.
Examples of suitable radicals R.sup.2, R.sup.4, R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.11 and R.sup.12 are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl.
Suitable radicals R.sup.2, R.sup.4, R.sup.6, R.sup.7, R.sup.8 and R.sup.9 are additionally n-pentyl, isopentyl, sec-pentyl, tert-pentyl, neopentyl, n-hexyl, n-heptyl, n-octyl and 2-ethylhexyl.
Suitable radicals R.sup.2, R.sup.4, R.sup.2 and R.su

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