Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Polymers from only ethylenic monomers or processes of...
Patent
1993-03-05
1994-11-01
Schofer, Joseph L.
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Polymers from only ethylenic monomers or processes of...
526216, 526258, 526315, 5263285, 525298, 5253267, 5253287, C08F 200, C08F22606, C08F21634, C08F22010
Patent
active
053608801
DESCRIPTION:
BRIEF SUMMARY
This invention relates to polymerisable porphyrins and methods for their manufacture, polymers formed therefrom and use of such polymers as films and coatings.
We have found that the condensation of a beta-unsaturated aldehyde and a pyrrole can give rise to a monomeric product which contains a porphyrin bearing unsaturated substituents. This monomeric material then readily polymerises to produce polymeric product. Similar products can be produced using other unsaturated or polymerisable aldehydes
According to the present invention there is provided a polymerisable material produced by the reaction of a pyrrole and an unsaturated or polymerisable aldehyde, preferably a beta-unsaturated aldehyde.
The pyrrole may be the unsubstituted pyrrole molecule itself, or it may bear substituents. Particulary preferred substituted pyrroles are those formed by addition to the pyrrole ring of acrylate or vinyl monomers. The preferred aldehydes are crotonaldehyde or acrolein.
The invention also includes polymers made from the above-described material and to films, coatings and other structures made from such a polymer.
The invention also extends to copolymers formed from the above-mentioned polymerisable material and at least one other polymerisable monomer of a known type. Examples of such co-monomers are vinyl monomers, such as styrene, and acrylic acid or acrylate monomers, such as acrylic acid itself or methyl methacrylate. The polymers of the invention will also initiate the radical polymerisation of such monomers.
The invention further extends to substrates having a coating of the above-mentioned polymers.
The polymerisable materials of this invention may be produced by the reaction of the major components, the pyrrole and the aldehyde, in the presence of an acid catalyst.
The acid catalyst may be an organic acid, such as acetic or propionic acid, or an acid anhydride, such as phthalic anhydride.
To illustrate the process of the invention by way of example, a dark viscous paint can be easily produced by mixing pyrrole, crotonaldehyde and propionic acid. If the mixture is allowed to stand at room temperature for a period of time (the induction time), it rapidly increases in viscosity and can then be painted onto some suitable substrate. The resultant black coating sets rapidly, is chemically inert and adheres strongly to glass and metal substrates.
The induction time (prior to the rapid polymerisation stage) can be varied from a few minutes to several hours by using different acids and/or varying the acid concentration. It is likely that during the induction period the tetracrotonyl porphyrin (TCP) (or tetraacrolein porphyrin (TAP)) molecule is formed, which when present at significant concentrations initiates further, rapid polymerisation of the aldehyde and pyrrole.
The reaction normally proceeds well at room temperature, but in some circumstances it may be advantageous to work at or near the thermodynamically favoured temperature of 55.degree. C.
The chemical composition of the resulting polymer is difficult to obtain but most likely consists of linear chains in a porphyrin star polymer matrix.
Due to the strongly adherent nature of the polymers of the invention, they can be used in areas of reasonably high mechanical/fluid work. The electronic nature of the ring nitrogens allows for a high degree of binding to metals ions. With the metal ion in place gases may also be selectively bound (c.f. haem). The monodispersity of pore size is also a noted advantage of this molecule. Taking the above attributes together, the polymers of the invention may find applications in the following areas: converted to ion selective detectors by coating with a thin film of the polymeric porphyrin. In addition, binding iron (II) to the porphyrin may also allow detection of the oxygen content of water. the porphyrin as it polymerises. The resultant copolymer may be used as a porous or non-porous coating material. these porphyrin polymers will combine with divalent heavy metal ions, also leads to the use of the polymers in the purificatio
Guthrie James T.
He Wei D.
Morris Richard A.
Pashley Richard M.
Senden Timothy J.
Cheno Wu C.
Schofer Joseph L.
The Acton and Memtec Ltd.
The Australian National University
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