POLYVIOLOGENS

• US 3,856,714 A
• Filed: 09/07/1973
• Issued: 12/24/1974
• Est. Priority Date: 09/07/1973
• Status: Expired due to Term

• Current Assignee: Myron S. Simon, Phyllis T. Moore
• Original Assignee: Myron S. Simon, Phyllis T. Moore
• Inventors: Simon, Myron S., Moore, Phyllis T.
• Primary Examiner(s): Goldstein, Melvin
• Assistant Examiner(s): Nielsen, E. A.
• Application Number:
  US05/395,255
• Time in Patent Office: 473 Days
• Field of Search: 260/2.2R,13,47CP,78R,78.4R,2R,79.3R,296D
• US Class Current: 525/54.21
• CPC Class Codes: C08G 69/26 derived from polyamines and polycarboxylic acids
• CPC Class Codes: C08G 73/0273 Polyamines containing heterocyclic moieties in the main chain
• CPC Class Codes: Y10S 526/923 Ethylenic monomers containing at least one salt group

Abstract

Novel polyviologen compounds useful in variable density lightfiltering devices are provided which have repeating units (in oxidized dicationic form) represented by the formula: WHEREIN R1 is propylene or a straight-chain alkylene group having from six to 12 carbon atoms; R2 is -H or a hydrocarbon group having from one to six carbon atoms; Z is a bivalent radical resulting from the removal of both active halogen atoms from an aromatic dihalide or from an aliphatic dicarboxylic acid dihalide having a straight four to eight carbon alkylene chain between terminal carboxylic acid halide groups; and X is an anion.

Claims

1. A POLYMER HAVING IN ITS STUCTURE REPEATING UNITS OF THE FORMULA:

2. A polymer as defined in claim 1 which is film-forming.

3. A polymer as defined in claim 2 having a molecular weight in excess of about 10,000.

4. A polymer as defined in claim 2 having an appendage substituent which is available subsequent to the formation of said film to enter into a condensation reaction with another reagent and thereby cross-link said polymer into a water-insoluble film.

5. A polymer as defined in claim 4 wherein said cross-linking substituent is a substituent on the aromatic nucleus of Z.

6. A polymer as defined in claim 5 wherein said nuclear cross-linking substituent is selected from the group consisting of halide, -OH, -SH, -COOH, -SO2OH, -CH2CH2OH, and -C6H5CH CHCOOH.

7. A polymer as defined in claim 1 wherein R2 is alkyl or aryl.

8. A polymer as defined in claim 1 wherein X is a simple anion selected from the group consisting of halide, sulfate, nitrate, acetate, carbonate, azide and cyanide.

9. A pOlymer as defined in claim 1 wherein X is a polymeric anion.

10. A polymer as defined in claim 9 wherein said polymeric anion is the polyanion of a cation exchange resin.

11. A polymer as defined in claim 9 wherein said polymeric anion is the polyanion of sodium carboxymethyl cellulose.

12. A polymer as defined in claim 1 wherein X is an internal anion and said polymer is an internal salt.

13. A polymer as defined in claim 12 wherein said internal anion is attached to the aromatic nucleus of Z.

14. A polymer as defined in claim 1 wherein Z is an carbocyclic dicarbonyl group, an aliphatic dicarbonyl group having a straight four to eight carbon alkylene chain between terminal carbonyl groups, a bivalent azine nucleus or a bivalent group having one bond to an azine nucleus and the other bond to an carbocyclic carbonyl group.

15. A polymer as defined in claim 1 wherein Z is:

16. A polymer as defined in claim 1 wherein Z is:

17. A polymer as defined in claim 1 comprising repeating units of the formula:

18. A polymer as defined in claim 1 comprising repeating units of the formula:

19. A polymer as defined in claim 1 comprising repeating units of the formula:

20. A polymer as defined in claim 1 comprising repeating units of the formula:

21. A polymer as defined in claim 20 which is cross-linked with an aliphatic diamine.

22. A copolymer comprising repeating units of the formulae:

23. A copolymer as defined in claim 22 wherein the ratio of A units to B units is 3 to 1.

24. A copolymer as defined in claim 23 which is cross-linked with an aliphatic diamine.

25. A polymer as defined in claim 1 which is water-soluble.

26. A water-insoluble cross-linked polymer having in its structure repeating units of the formula:

27. A cross-linked polymer as defined in claim 26 wherein Z is a carbocyclic dicarbonyl group, an aliphatic dicarbonyl group having a straight four to eight carbon alkylene chain between terminal carbonyl groups, a bivalent azine nucleus or a bivalent group having one bond to an azine nucleus and the other bond to a carbocyclic carbonyl group.

28. A cross-linked polymer as defined in claim 26 wherein said cross-linking substituent is attached to the aromatic nucleus of Z.

29. A cross-linked polymer as defined in claim 28 wherein said cross-linking substituent is selected from the group consisting of halide, -OH, -SH, -COOH, -SO2OH, -CH2CH2OH and -C6H5CH CHCOOH.

30. A cross-linked polymer as defined in claim 26 wherein said polymer is cross-linked with an aliphatic diamine.