Polymers of 2,7-dioxabicyclo[3.2.1]octane derivatives

Details Polymers of 2,7-dioxabicyclo[3.2.1]octane derivatives Polymers of 2,7-dioxabicyclo[3.2.1]octane derivatives

1998-07-13

2000-06-20

Cain, Edward J.

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

Synthetic resins

From heterocyclic reactant containing as ring atoms oxygen,...

528417, C08G 5900

Patent

active

060779322

DESCRIPTION:

BRIEF SUMMARY
The invention relates to polymers obtainable by polymerizing or copolymerizing 2,7-dioxabicyclo[3.2.1]octane derivatives of the formula ##STR2## where X, X', Y, Y', Z and Z' each independently are a C.sub.1 -C.sub.20 hydrocarbon radical or hydrogen.
The invention also relates to the use of polymers for producing coatings and moldings, especially including structured coatings and moldings.
The production of coatings and moldings by subjecting free-radically or cationically polymerizable compounds to radiation curing is a matter of general knowledge. The radiation curing of acrylate compounds has acquired particular industrial importance. In the case of acrylate compounds, however, there is the fundamental problem that the photopolymerization is inhibited by oxygen.
The search is therefore on for monomers, especially cationically polymerizable monomers, that are suitable for producing coatings and moldings.
Also of industrial importance are structured (patterned) coatings and moldings, such as printed circuit boards, printing plates, etc.
For producing such structured systems use is made in particular of photoresists, i.e. coatings whose solubility changes on irradiation with high-energy light. Controlled irradiation and subsequent removal of the compounds that have become soluble by irradiation produce structures.
The search is therefore also on for polymers suitable as photoresists.
It is an object of the present invention to find polymers suitable for producing coatings and moldings by radiation curing.
We have found that this object is achieved by the polymers defined above. We have also found processes for producing the polymers and uses of the polymers.
The novel polymers contain preferably from 0.05 to 100% by weight, particularly preferably from 0.5 to 100% by weight and, with very particular preference, from 1 to 100% by weight of the compounds of the formula I as monomer or comonomer.
Other polymers particularly suitable for coatings and moldings are those containing from 10 to 100% by weight, from 30 to 100% by weight, from 50 to 100% by weight or from 80 to 100% by weight of the compounds of the formula I.
Preferred compounds of the formula I are those in which X, X', Y, Y', Z, Z' each independently are hydrogen, C.sub.1 -C.sub.8 -alkyl, especially C.sub.1 -C.sub.4 -alkyl, or phenyl.
With particular preference at least 4 of X, X', Y, Y', Z and Z' are hydrogen.
With very particular preference, all of the radicals are hydrogen; in other words, the compound is 2,7-dioxabicyclo[3.2.1]octane of the formula ##STR3## 2,7-dioxabicyclo[3.2.1]octane and its derivatives can be prepared by a process which comprises ether in the presence of a halogenating agent thus ##STR4## where R is a hydrocarbon radical, Hal is halogen and X, X', Y, Y', Z and Z' each independently are hydrogen or a C.sub.1 -C.sub.20 hydrocarbon radical, ##STR5## c) then eliminating the alcohol ROH thus ##STR6## d) and effecting the ring closure to the 2,7-dioxabicyclo[3.2.1]octane or derivative thereof, thus ##STR7##
The statements made below relate to preferred embodiments of the process.
In step a) a vinyl ether, especially an alkyl vinyl ether, is reacted with a but-2-ene-1,4-diol thus ##STR8## where Hal is halogen, R is a hydrocarbon radical, especially alkyl and preferably C.sub.1 -C.sub.20 -alkyl, and X, X', Y, Y', Z and Z' each independently are a C.sub.1 -C.sub.20 hydrocarbon radical or hydrogen.
Hal is preferably bromine and R is preferably C.sub.1 -C.sub.8 -alkyl, especially C.sub.1 -C.sub.4 -alkyl and, with very particular preference, C.sub.2 -alkyl. X, X', Y, Y', Z and Z' each independently are preferably hydrogen or C.sub.1 -C.sub.8 -alkyl, especially C.sub.1 -C.sub.4 -alkyl, or phenyl.
With particular preference at least 4 of X, X', Y, Y', Z and Z' are hydrogen. With very particular preference, each of X, X', Y, Y', Z, Z' is hydrogen.
Step a) is preferably conducted in the presence of a halogenating agent, for example a brominating agent, especially N-bromosuccinimide.
The vinyl ether and the but-2-ene-1,4-diol derivative ar

REFERENCES:
"Polymerization of bicyclic acetals", Hirasawa et al, Macromolecules, ed 21, Nr. 6, p 1566 (1988).
"Sterically Controlled cationic Propagation . . . ", Sumitomo et al, Die Macromolecules Chemie, Nr. 6, p 11, 1986.

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