Amino compounds as processing stabilizers for thermoplastic mate

Details Amino compounds as processing stabilizers for thermoplastic mate Amino compounds as processing stabilizers for thermoplastic mate

1994-10-12

1996-03-05

Mulcahy, Peter D.

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

Synthetic resins

Processes of preparing a desired or intentional composition...

524247, 524248, C08K 320

Patent

active

054968771

DESCRIPTION:

BRIEF SUMMARY
During the processing of thermoplastic materials at elevated temperatures of from 250.degree. to 350.degree. C., for example during extrusion, chain decomposition or cross-linking reactions occur, especially in the presence of atmospheric oxygen, which undesirably change the mechanical and esthetic properties of the polymers and in some cases even render the plastic unusable.
In order to prevent these undesirable changes, processing stabilizers must be added to the plastics.
The prior art compounds used for this purpose include sulfides, phosphites, phosphonites or phenolic antioxidants or mixtures of such compounds (see R. Ga/ chter and H. Mu/ ller, Taschenbuch der Kunststoff-additive, Carl Hanser Verlag, 3rd edition, Munich, Vienna, 1990, p. 42-103). DE-A 11 61 897 describes the stabilization of organic substances against damage by atmospheric oxygen using di- or tetramines containing specific aromatic radicals. However, the prior art compounds are not always satisfactory as regards effectiveness, thermal stability, low tendency to discoloration and compatibility.
It is an object of the present invention to provide novel, easily accessible processing stabilizers which do not have these disadvantages.
We have found that surprisingly this object is achieved by means of the amino compounds as claimed in claim 1.
The variable m is 2 or preferably 3. The variable n is an integer from 1 to 6, and n is preferably 1 or 2.
Alkyl groups for R.sup.1 to R.sup.5 may be branched or unbranched.
C.sub.1 -C.sub.18 -alkyl groups for R.sup.1 to R.sup.5 are for example methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, n-pentyl, 2-methylbutyl, 2- or 3-methylpentyl, n-hexyl, n-heptyl, n-octyl, 3-methylhexyl, n-decyl, tridecyl, lauryl or stearyl. R.sup.1 and R.sup.2 are preferably methyl, and R.sup.3 is preferably C.sub.1 - to C.sub.18 -alkyl.
C.sub.3 -C.sub.8 -alkenyl groups for R.sup.1 to R.sup.5 are for example 2-butenyl, 2-pentenyl, 2-hexenyl, 2-heptenyl or 2-octenyl and especially allyl.
C.sub.5 -C.sub.12 -cycloalkyl groups for R.sup.1 to R.sup.5 are for example cyclopentyl, cyclohexyl, 4-methylcyclohexyl, cycloheptyl, cyclooctyl or cyclododecyl. Cyclohexyl is preferred.
C.sub.7 -C.sub.12 -phenylalkyl radicals for R.sup.1 to R.sup.5 are for example benzyl, 2-, 3- or 4-methylbenzyl, phenylethyl, phenylpropyl, phenylbutyl, 2-, 3- or 4-methoxybenzyl, 2-, 3- or 4-ethylbenzyl, 2-, 3- or 4-ethoxybenzyl or 4-dodecylbenzyl. Benzyl is preferred.
Hydrogen or methyl are particularly preferred for R.sup.1 and R.sup.2 and for R.sup.4 and R.sup.5. In addition, a group of the formula ##STR3## is particularly preferred for R.sup.3.
The radical X is oxygen or NR.sup.3, where R.sup.3 has the specified meaning.
3- to 12-membered saturated or unsaturated heterocyclic radicals ##STR4## are for example: ##STR5## wherein .alpha. is a number between 0 and 17.
Groups derived from morpholine or piperazine are preferred.
If n=1, A may for example be, in addition to hydrogen: C.sub.3 - to C.sub.24 -alkenyl such as allyl, 1-pentenyl, 1-hexenyl, 1-heptenyl, 1-octenyl, 1-decenyl or 1-dodecenyl. Oleyl is preferred.
If A is C.sub.1 - to C.sub.60 -alkyl which may be interrupted by up to 29 carbon atoms or NR.sup.3, A is for example: ##STR6## wherein: p is an integer from 0 to 24,
Of these groups, CH.sub.3 -(CH.sub.2).sub.p radicals with p equal to 11 to 17 are preferred.
Examples of cycloalkyl groups A are: cyclopropyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 2,4-dimethylcyclohexyl, cycloheptyl, cyclooctyl or cyclododecyl.
Examples of C.sub.7 - to C.sub.20 -bicycloalkyl groups A are: adamantyl, norbornyl or 1- or 2-perhydronaphthyl.
If n>1, A denotes polyvalent organic radicals. Examples of C.sub.2 - to C.sub.24 -alkenyl groups A are: ##STR7## wherein a is an integer from 2 to 24.
C.sub.4 - to C.sub.60 -alkylene groups, which may be interrupted up to 29 times by NR.sup.3 or oxygen, are for example: ##STR8## where b=1 to 29,
C.sub.3 - to C.sub.12 -alkylene radicals which may carry up to 6 hydroxyl, C.sub.1 - to C.sub.4 -alkoxy, amino, or C.s

REFERENCES:
patent: 3198763 (1965-08-01), Peterli
patent: 3485786 (1969-12-01), Rombusch
Ga/ chter und Mu/ ller Taschenbuch der Kunststoff Additive, Carl Hanser Verlag, 3rd ed., pp. 42-103 (1990).

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