Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – From carboxylic acid or derivative thereof
Patent
1996-03-22
1999-03-09
Hampton-Hightower, P.
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
From carboxylic acid or derivative thereof
528 59, 528 63, 528 66, 528170, 528183, 528192, 528220, 528229, 528272, 528288, 528310, 528322, 528324, 528339, 528345, 252 884, 25218626, 252304, 2523671, 424 701, 428395, C08G 7300
Patent
active
058802525
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to novel pyrrolidonyl-containing polyesters and polyamides, to processes for their preparation, and to the use of these pyrrolidonyl-containing polyesters and polyamides in specific industrial areas.
Polyvinylpyrrolidone (PVP) and copolymers of vinyl pyrrolidone prepared by means of free radicals, for example using vinyl acetate, have hitherto found use in various industrial areas. In particular, their properties are utilized as complexing agents, film-forming agents, depot formers, enzyme supports, binders and adhesive raw materials. The applications are in the cosmetics and pharmaceuticals sectors and in the foodstuffs, textiles, detergents and not least in the polymers areas, for example as solubilizers or protective colloids.
However, PVP and copolymers thereof have a number of drawbacks in these applications, in particular their unsatisfactory biodegradability or eliminability, their toxicity potential (monomeric vinyl pyrrolidone has been classified as carcinogenic in animal experiments) and in some cases their incompatibility with certain saccharides (for example in mixtures of PVP with maltodextrins). In addition, the applicational properties of PVP and copolymers thereof are frequently also unsatisfactory.
U.S. Pat. No. 2,993,021 (1) discloses polyesters obtained by polycondensation of bispyrrolidone derivatives of the structure ##STR2## where R is an alkylene, oxaalkylene, thiaalkylene or azaalkylene bridge having 2 to 12 carbon atoms, for example 1,2-ethylene or 1,3-propylene, with a polyhydroxyl compound, for example ethylene glycol or propylene glycol. These polyesters are suitable, under certain circumstances, as plasticizers for plastics and for the preparation of alkyd resins, which, as is known, play an important role as vehicles in the paints industry.
The Israel Journal of Chemistry, Vol. 10 (1972), 949-957 (2) discloses highly heat-resistant polyamides prepared by reacting aromatic diamines, such as benzidine, 4,4'-diaminodiphenyl sulfone, 4,4'-diaminodiphenyl ether or p-phenylenediamine, with bispyrrolidonedicarboxylic acids obtained by reacting itaconic acid with said aromatic diamines. These polyamides apparently have low solubility, since they only dissolve in concentrated sulfuric acid and some partially dissolve in dimethylformamide or dimethyl sulfoxide. A suggested use is in adhesive formulations.
It is an object of the present invention to provide novel materials as replacement for PVP and copolymers thereof in said areas of application which do not have the disadvantages of the prior art.
We have found that this object is achieved by pyrrolidonyl-containing polyesters and polyamides of the formulae I to III ##STR3## where R is hydrogen or C.sub.1 - to C.sub.4 -alkyl, where two radicals R can be linked to one another to form a six-membered ring, more non-adjacent oxygen atoms, sulfur atoms or functional groups --NR--, where the nitrogen atom can be protonated or quaternized, --CO--, --CO--O--, --CO--NR--, --SO-- or SO.sub.2 --, and which may carry additional functional groups --COOH or --SO.sub.3 H, C.sub.6 - to C.sub.20 -cycloalkylene, C.sub.6 - to C.sub.20 -arylene, which may be interrupted by oxygen, sulfur or --NR--, --SO-- or --SO.sub.2 -- and may additionally carry functional groups --COOH or --SO.sub.3 H, or a mixture of such groups, ##STR4## where B is C.sub.1 - to C.sub.20 -alkylene, which may be interrupted by one or more non-adjacent oxygen atoms, sulfur atoms or functional groups --NR--, where the nitrogen atom may be protonated or quaternized, --CO--, --CO--O--, --CO--O--, --CO--NR--, --SO-- or --SO.sub.2 --, and which may carry additional functional groups --COOH or --SO.sub.3 H, C.sub.6 - to C.sub.20 -cycloalkylene or a mixture of such groups, or is a mixture of groups of the formula IV with groups A, and
C.sub.1 - to C.sub.4 -alkyl R.sup.1 is ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl or, in particular, methyl. If two --NR-- groups are linked to one another by a C.sub.1 - to C.sub.3 -alkylene group, the two
REFERENCES:
patent: 2993021 (1961-07-01), Bavley et al.
patent: 4418189 (1983-11-01), Morello
Israel Journal of Chemistry, vol. 10, 1972, pp. 949-957.
Breitenbach Jorg
Hossel Peter
Kim Son Nguyen
Lang Siegfried
Sanner Axel
BASF - Aktiengesellschaft
Hampton-Hightower P.
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