Ring opening monomers

Details Ring opening monomers Ring opening monomers

1995-07-20

1997-09-09

Schofer, Joseph L.

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

Synthetic resins

Polymers from only ethylenic monomers or processes of...

549 10, 549267, 549271, 5263285, 526342, 526347, 526266, C08F22806, C08F22400, C08F22010, C08F22044, C08F21208, C07D32702, C07D32710

Patent

active

056658397

DESCRIPTION:

BRIEF SUMMARY
This invention relates to a new class of ring opening monomers, that is unsaturated organic compounds which when used as monomers undergo ring opening on free radical polymerisation. Ring opening monomers are important in minimising volume shrinkage during polymerisation. Additionally, ring opening monomers are useful in providing an alternative method of incorporating functionalities such as amide, ester or carbonate into the backbone of a polymer. Conventionally, such functionalities are introduced by step growth polymerisation (i.e. polyesterification) rather than chain growth polymerisation (i.e. free radical). The limitations of step growth polymerisation are that (a) very high conversion is required for high molecular weight polymer and (b) elimination products (such as water or HCl) are formed and require removal. In contrast, chain growth polymerisation (free radical or ionic) results in very high molecular weight polymer from the beginning of the polymerisation with no elimination products generally being formed.
There are many types of ring opening monomers available for cationic or anionic polymerisation. However, there are only a limited number of ring opening monomers available for free radical polymerisation. A review by Endo et al. in Chapter Five of New Methods for Polymer Synthesis, Plenum Press, New York 1992, summarises the present state of the art. The major types of free radically polymerizable, ring opening monomers are vinyl cyclopropanes, various cyclic vinyl ethers, cyclic ketene acetals (U.S. Pat. No. 4,857,620 to PPG Industries, Inc.), spiro ortho esters and spiro ortho carbonates. These, however, suffer from limitations. Ring opening of vinyl cyclopropanes is a reversible process and substituents that favour ring opening may also inhibit polymer growth by excessive stabilisation of the ring-opened propagating radical. The oxygenated monomers listed above generally are extremely sensitive to trace mounts of acid. This makes their synthesis and subsequent storage difficult. Furthermore ring opening is not guaranteed and the final polymers can contain various proportions of opened and unopened rings. In addition, the spiro ortho esters and spiro ortho carbonates have the following disadvantages: from occurring. This can make the polymerisation somewhat irreproducible. such as styrene and methyl methacrylate (and monomers of similar reactivity). solvents and monomers. The book Expanding Monomers, Eds. Sadhir, R. K. and Luck, R. M. CRC Press, Boca Raton, 1992, details the chemistry and use of spiro ortho esters and carbonates.
The present invention provides a new class of organic compound that undergoes ring opening by free radical polymerisation. These compounds are readily soluble in common organic solvents and monomers. They are stable to acidic and basic conditions, and are easily handled with no special precautions required. Because they contain an acrylate skeleton, they can readily copolymerise with the major commercial monomers of similar reactivity such as acrylates, methacrylates, acrylonitrile, methacrylonitrile, styrenes and related monomers.
Accordingly the present invention provides compounds of the Formula 1 ##STR2## wherein: R.sup.1 and R.sup.2 are independently selected from the group comprising hydrogen, C.sub.1 to C.sub.6
Preferably X is S and Y is O.
Suitable linking functionalities for Z are --(CWT).sub.n --O--(CO)--O--(CWT).sub.m --,--(CWT).sub.n --, --(CWT).sub.n --O--(CO)--(CWT).sub.m --, --(CWT).sub.n --O--(CWT).sub.m --, --(CWT).sub.n --CO--(CWT).sub.m --, --(CWT).sub.n --(C.dbd.O)--, --(CWT).sub.n --S--(CWT).sub.m --, --(CWT).sub.n --S--S--(CWT).sub.m --, --(CWTCWT).sub.n --, phenylene, or substituted phenylene (where W, T are independently selected from hydrogen, C.sub.1 to C.sub.6 alkyl, C.sub.1 to C.sub.6 haloalkyl, phenyl, substituted phenyl or halogen and m,n are whole numbers). The ring system in Formula 1, preferably contains from six to 50 atom.
In this specification "substituted" group means that a group may be substituted with one or more groups s

REFERENCES:
patent: 4889938 (1989-12-01), Kristen et al.

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