Iminoimidazolidinedione and parabanic acid polymers containing imide groups

Abstract

Novel iminoimidazolidinedione polymers containing imide groups (hereinafter PIPA-IM) are prepared from mixtures of dianhydrides, hydrogen cyanide and diisocyanates in an appropriate solvent and with an appropriate catalyst. The cyanide ion is an effective catalyst for all of the reactions involved. Hydrolysis of these polymers produces novel parabanic acid polymers containing imide groups (hereinafter PPA-IM).

What is claimed is: 
     
       1. As a composition of matter a new class of polymers .[.which are.]. .Iadd.selected from the group of .Iaddend.iminoimidazolidinedione polymers containing imide groups .[.or their hydrolysis derivatives, which are parabanic.]. .Iadd.and iminoimidazolidinedione-parabanic .Iaddend.acid polymers containing imide groups. 
     
     
       2. The polymers of claim 1 which have at least one polyimide moiety and at least one polyparabanic acid moiety. 
     
     
       3. The polymers of claim 1 which have at least one polyimide moiety and at least one iminoimidazolidinedione moiety. 
     
     
       4. A polymer according to claim 1 which has at least one each of the units set forth below: ##STR5## wherein X=NH or O .Iadd.R is an organic moiety of a carboxylic dianhydride and R' is an organic moiety of a diisocyanate.Iaddend.. 
     
     
       5. A polymer according to claim 4 which contains at least two units as set forth below: ##STR6## wherein X=NH or O .Iadd.R is an organic moiety of a carboxylic dianhydride and R' is an organic moiety of a diisocyanate.Iaddend.. 
     
     
       6. The polymer of claim 1 wherein said .[.dianhydride is.]. .Iadd.imide groups are .Iaddend.derived from pyromelletic anhydride and the .[.isocyanate derived.]. .Iadd.iminoimidazolidinedione and parabanic acid .Iaddend.portion is .Iadd.derived .Iaddend.from a diphenylether diisocyanate. 
     
     
       7. A method of preparing iminoimidazolidinedione polymers containing imide groups which comprises reacting in an appropriate solvent, a selected molar portion of dianhydrides, diisocyanates, and hydrogen cyanide in the presence of a catalyst. 
     
     
       8. The method of preparing polymers containing imide groups and parabanic acid groups by hydrolyzing iminodazolidinedione polymers containing imide groups prepared by the process of claim 7. 
     
     
       9. A method according to claim 7 in which the anhydride has the following formula: ##STR7## in which formula R represents a 2y-valent aliphatic, aliphatic-aromatic, or aromatic radical and y represents an integer from 2 to 3 and which the isocyanate has the following formula: R'(nco) x  is which R' is a C 4  to C 60  hydrocarbon or substituted hydrocarbon constituent, selected from the group consisting of aliphatic, alicyclic, aromatic constituents, or combinations and mixtures thereof in which the functionally substituted derivatives thereof will not react with isocyanate groups and X is 2 to 5.   
     
     
       10. A method according to claim 7 wherein said reaction takes place in the presence of a catalyst which is a cyanide ion. 
     
     
       11. A process according to the above claim 10 in which said cyanide ion is derived from sodium cyanide. 
     
     
       12. A process according to claim 7 above wherein the solvent utilized to carry out said reaction is an aprotic dipolar solvent. 
     
     
       13. A process according to claim 9 in which the isocyanate (NCO) group is substituted by NCS. 
     
     
       14. The process according to claim 7 in which a monoanhydride having a C 4  to C 60  hydrocarbon or substitute hydrocarbon constituent selected from aliphatic, alicyclic, aromatic constituents, or combinations and mixtures thereof, in which the functionally substituted derivatives thereof will not react with isocyanate groups is used as a chain terminating agent. .Iadd.15. The polymer of claim 1 wherein said imide groups are derived from benzophenone tetracarboxylic dianhydride and the iminoimidazolidinedione and parabanic acid portion is derived from a diphenyl methane diisocyanate. .Iaddend.