Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – From carboxylic acid or derivative thereof
Patent
1990-06-12
1992-11-17
Kight, III, John
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
From carboxylic acid or derivative thereof
528176, 528179, 528183, 528188, 528222, 528226, 528229, 528338, 528339, 528340, 528348, 528350, 528353, C08G 7314, C08G 6912, C08G 6926
Patent
active
051644762
DESCRIPTION:
BRIEF SUMMARY
DESCRIPTION
The invention describes soluble and/or fusible heat-stable polyimides and polyamidoimides and processes for their preparation.
The heat-stable polymers which are the most important industrially to date are the completely aromatic polyimides, which have extreme heat stabilities but are neither fusible nor soluble and therefore can be processed only with much effort and expensively. The somewhat less heat-stable aromatic polyamides are also non-fusible and insoluble or only slightly soluble in most organic solvents, so that their processing to fibers or films from solution is associated with great difficulties. The difficult processability makes these heat-stable polymers quite considerably more expensive and therefore excludes them from a number of interesting uses.
Attempts to develop fusible or more readily soluble heat-stable polymers--for example by incorporation flexible chain elements (--CH.sub.2 --, --O--, --S-- or --CO--) or sterically hindering groups have indeed been successful, but to date have always led to a usually considerable loss of heat stability. These products also include the polyamidoimides and polyester-imides in which aromatic amide and imide or ester and imide groups are arranged randomly, these usually being soluble or having thermoplastic properties but likewise having a low heat stability (U.S. Pat. No. 3,895,064).
The actual solution to the problem in the field of heat-stable polymers thus still lies in the development of novel products of high heat stability and at the same time good processability.
The object of the present invention was to develop novel polyimides and polyamidoimides which, as well as having an extreme heat stability, are soluble and/or fusible in the cyclized form and thus can easily be processed by conventional methods.
It has now been found that this object can be achieved with the aid of polyimides or polyamidoimides which contain aromatic tri- or tetracarboxylic acid radicals and the radicals of at least two different diamines as chain units, at least one of which consists of benzene rings bonded via --S-- and --SO.sub.2 -- bridges.
The present invention accordingly relates to soluble and/or fusible polyimides or polyamidoimides of the general formula I ##STR3## in which R denotes a divalent radical of the formula II ##STR4## Ar denotes trivalent or tetravalent aromatic radicals which are optionally substituted by one or more halogen atoms, or mixtures thereof, it being possible for the trivalent aromatic radical optionally additionally to contain a carboxyl group as a substituent, X denotes the amide radical --CO--NH-- if Ar is trivalent, and if Ar is tetravalent denotes the imide radical of the formula III ##STR5## N in each case being bonded to R, R.sub.1 denotes divalent aromatic radicals of the formulae IV to VIII ##STR6## or mixtures thereof, in which A stands for --CH.sub.2 --, --C(CH.sub.3).sub.2 --, --O--, --S--, --SO--, --SO.sub.2 --, --CO--, --COO--, --CO--NH--, --NH--, --(N--alkyl)-- having 1 to 20 C atoms, --(N--aryl)-- having 6 to 20 C atoms or --N.dbd.N--, and n denotes an integer from 2 to 200.
All the known tri- or tetravalent aromatic radicals Ar which are derived, in particular, from the corresponding tri- or tetracarboxylic acids or their derivatives, such as, for example, anhydrides, esters or acid chlorides, are possible according to the invention. Examples of these are radicals of aromatics, fused aromatics and heteroaromatics and derivatives thereof. Preferred tri- or tetravalent radicals Ar are the benzene radical or the benzophenone radical. Those polyamidoimides of the general formula I ##STR7## which contain both trivalent and tetravalent radicals Ar are furthermore preferred. The radicals Ar can also be substituted.
If the trivalent radical Ar additionally contains a carboxyl group as a substituent, that is to say is derived from a tetracarboxylic acid, the polymer according to the invention is in the form of an amide acid which contains a carboxyl group in the ortho-position relative to the amide bond.
The polyi
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Greber Gerd
Gruber Heinrich
Sychra Marcel
Chemie Linz Gesellschaft m.b.H.
Hampton-Hightower P.
Kight III John
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