Radical polymerizable composition containing a compound having pi-electron conjugated structure

• US 4,962,158 A
• Filed: 02/25/1988
• Issued: 10/09/1990
• Est. Priority Date: 02/25/1987
• Status: Expired due to Term

• Current Assignee: Showa Denko KK
• Original Assignee: Showa Denko KK
• Inventors: Kobayashi, Masao, Otsuka, Reiko
• Primary Examiner(s): Briggs, Sr., Wilbert J.
• Application Number:
  US07/160,431
• Time in Patent Office: 957 Days
• Field of Search: 525/284, 525/417, 525/279, 526/256, 526/258, 526/270, 526/72, 522/118, 522/119
• US Class Current: 525/279
• CPC Class Codes: C08L 2666/02 Organic macromolecular compounds, natural resins, waxes or and bituminous materials
• CPC Class Codes: C08L 65/00 Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain C08L7/00 - C08L57/00, C08L61/00 take precedence; Compositions of derivatives of such polymers
• CPC Class Codes: H01B 1/127 comprising five-membered aromatic rings in the main chain, e.g. polypyrroles, polythiophenes
• CPC Class Codes: H01B 1/128 comprising six-membered aromatic rings in the main chain, e.g. polyanilines, polyphenylenes
• CPC Class Codes: H01M 4/60 of organic compounds
• CPC Class Codes: Y02E 60/10 Energy storage using batteries

Abstract

A radical polymerizable composition comprising

(A) a compound having a pi-electron conjugated structure and

(B) a radical polymerizable compound, which is useful for molding into an arbitrary shape, which can be rendered electrically conductive and which is, therefore, useful as a material for electrodes or circuits in the electrical and electronic industry.

Claims

1. A radical polymerizable composition comprising:

(A) a compound having a pi-electron conjugated structure comprising a repeating unit represented by formula (I) ##STR3## wherein X represents NH, S, O, Se or Te;

Y₁ and Y₂, which may be the same or different, each represents a hydrogen atom, a substituted or unsubstituted alkyl group having from 1 to 12 carbon atoms, an alkoxy group, an alkoxycarbonyl group, an aryloxycarbonyl group, and alkoxysulfonyl group, an aryloxysulfonyl group or an amido group; and

the parentheses indicate a repeating unit;

(B) a radical polymerizable compound; and

(C) a radical polymerization initiator.

2. A radical polymerizable composition as claimed in claim 1, wherein said compound (A) is a thiophene oligomer, a pyrrole oligomer, poly[2,5-thienylene-3-(methyl 2-ethanesulfonate)], poly(3-hexyl-2,5-thienylene), poly(3-methoxythiophene), or poly[2,5-pyrrole-1-(methyl 2-butanesulfonate)].

3. A radical polymerizable composition as claimed in claim 2, wherein said compound (A) is poly[2,5-thienylene-3-(methyl 2-ethanesulfonate)] represented by formula:

##STR4## wherein the parentheses indicate a repeating unit.

4. A radical polymerizable composition as claimed in claim 1, wherein X represents NH or S, and Y₁ and Y₂ each represents a hydrogen atom, an substituted or unsubstituted alkyl group having from 1 to 12 carbon atoms, or an alkoxy group having from 1 to 4 carbon atoms.

5. A radical polymerizable composition as claimed in claim 1, wherein the number of the repeating units in said compound (A) ranges from 50 to 10,000, provided that, when Y₁ and Y₂ in the repeating unit of formula (I) are a hydrogen atom and/or an unsubstituted alkyl group having from 1 to 3 carbon atoms, the number of the repeating units ranges from 5 to less than 50.

6. A radical polymerizable composition as claimed in claim 5, wherein said compound (A) has the repeating unit represented by formula (I), Y₁ and Y₂ each represents a hydrogen atom, a substituted alkyl group having 2 or 3 carbon atoms, and/or a substituted or unsubstituted alkyl group having from 4 to 12 carbon atoms provided that Y₁ and Y₂ are not hydrogen atoms at the same time, X represents NH or S, and the number of the repeating units ranges from 50 to 10,000.

7. A radical polymerizable composition as claimed in claim 1, wherein said compound (B) is styrene, epoxy acrylate, diallylidene pentaerythritol, epoxy methacrylate, trimethylolpropane triacrylate, methyl methacrylate, N-vinylpyrrolidone, or a mixture thereof.

8. A radical polymerizable composition as claimed in claim 1, wherein said compound (A) is present in an amount of from 5 to 50% by weight based on the total weight of said compound (A) and said compound (B).

9. A radical polymerizable composition as claimed in claim 8, wherein said compound (A) is contained in an amount of from 10 to 30% by weight based on the total weight of said compound (A) and said compound (B).

10. A radical polymerizable composition as claimed in claim 6, wherein Y₁ and Y₂ each represents a hydrogen atom or a substituted or unsubstituted alkyl group having from 4 to 12 carbon atoms, provided that Y₁ Y₂ are not hydrogen atoms simultaneously.

11. A radical polymerizable composition as claimed in claim 6, wherein Y₁ and Y₂ each represents a hydrogen atom or a substituted or unsubstituted alkyl group having from 6 to 10 carbon atoms, provided that Y₁ and Y₂ are not hydrogen atoms simultaneously.

12. A radical polymerizable composition as claimed in claim 1, wherein said radical polymerization initiator is selected from the group consisting of a peroxide, an azo compound and a carbonyl compound.

13. A radical polymerizable composition as claimed in claim 1, wherein X is sulfur.