Polymers of 3,4-substituted pyrrole compounds and their preparat

Details Polymers of 3,4-substituted pyrrole compounds and their preparat Polymers of 3,4-substituted pyrrole compounds and their preparat

1987-04-27

1989-03-28

Ivy, C. Warren

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

Synthetic resins

Polymers from only ethylenic monomers or processes of...

526243, 526247, 526252, 548518, C08F22606

Patent

active

048165360

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELD

This invention relates to new polymers of pyrrole compounds and more particularly to the polymers of 3,4-substituted pyrrole compounds, their preparation method and the laminates of the polymer on an electrode plate.


BACKGROUND TECHNOLOGIES

The electrochemical polymerization of 5-membered and 6-membered heterocyclic compounds, particularly of pyrrole, is laid open in the specification of U.S. Pat. No. 3,574,072.
That the anodic oxidative polymerization of pyrrole in the presence of a conductive salt results in forming film with the conductivity of less than 10.sup.2 S cm.sup.-1 on the anode is described in A. F. Diaz, et. al: J.C.S. Chemical Communication (J.C.S. Chem. Comm. P635 (1979)).
It is defined in this technical field that polymer film containing the anion of the conductive salt and formed on the anode is said to be doped in the P type (oxidation state) and the state of which the anion, a dopant, is taken out from the inside of the molecule is said a undoping state (reduction state). The polymer film is known to have high conductivity in the doping state and extremely low conductivity in the undoping state, and to display the electrochromism when changing between the two states.
The polymers of 3,4-substituted pyrrole, especially of 3,4-asymmetrically substituted pyrrole compounds have general descriptions but few of them have been synthesized. No documents describing particularly polymers of pyrrole compounds having an electron attractive substituent at C.sub.3 or C.sub.4 have not been yet known.
The aforementioned polymer film of pyrrole compounds display the electrochromism, and have however no clear beautiful color changes. When letting stand alone in the air in the undoping state, the film is oxidized to change the color to black and thus does not exist stable in the undoping state. The polymers are usually insoluble and not melting.
Therefore, industrially useful materials or electronic devices employing the film have not been obtained yet.


INDICATION OF INVENTION

The present invention aims at offering the new polymers of 3,4-substituted pyrrole compounds, which have clear color changes and exist stable in the air even in the undoping state, and their preparation methods.
This invention has particular purposes of offering the polymers of 3,4-asymmetrically substituted pyrrole compounds and the polymers soluble in alkaline aqueous solvents, among the above polymers.
In addition, an offer of the laminates made by laminating the film of the said polymer on an electrode plate and applicable as electro chromic components is also one of the purposes of the invention.
This invention relates to that a pyrrole compound represented by the following general formula (1) ##STR1## (where at least one of X and Y is an electron attractive substituent with 0.30-0.80 of the Hammett's substituent constant (.sigma.p), and if only one of X and Y is the above electron attractive substituent, the other is hydrogen, an alkyl radical, a benzyl radical, or a non-substituted or substituted phenyl radical, and Z is hydrogen or an lower alkyl radical) is polymerized by electrolytic oxidation in the presence of a conductive salt, or by chemical oxidation in the presence of an oxidizing agent, resulting in giving the polymers of 3,4-substituted pyrrole compounds, which are represented by the following general formula (2) ##STR2## (where X, Y and Z have the same meaning as the above and n is an integer of 2 or larger).
In this invention, the pyrrole compound used as a material and its polymer have, as depicted in general formulae (1) and (2), at least an electron attractive substituent with the Hammett's substituent constant (.sigma.p) within the range of 0.3-0.80 at C.sub.3 or C.sub.4. The substituent includes NO.sub.2, --SO.sub.2 NH.sub.2, --CF.sub.3, --OCF.sub.3, --SCF.sub.3, --CN, --NCS, --CHO, --COOH, --CH.sub.2 COOH, --CONH.sub.2, --CONHOH, --SOR, --SO.sub.2 R, --OSO.sub.2 R, --CF.sub.2 CF.sub.3, --COR, --SCOR, --OCOR, --COOR, --CONHR, --CHNOR, --CHNNHC(S)NH.sub.2, --P(R).sub.2 D ,(O)(OR).sub.2,

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