8-alkyl-8-tricyclodecanyl (meth)acrylate and method of...

Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters

Reexamination Certificate

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Reexamination Certificate




1. Field of the Invention
The present invention relates to a novel tricyclodecanyl (meth)acrylate compound and a method of producing the same, and more particularly, to 8-alkyl-8-tricyclodecanyl (meth)acrylates and a method of producing the same.
2. Description of the Related Art
Acrylates or methacrylates are useful monomers which are polymerized solely or copolymerized with other monomers to provide various kinds of polymers exhibiting excellent performance. The thus-produced polymers generally have excellent weather resistance and transparency. Also, according to the kinds of ester substituents, polymers of various performance levels can be produced. Specifically, in the case where the ester substituent is a bulky alicyclic compound which has low chemical reactivity, the polymers can be commercially used as various flame retardants and much attention is being paid to the production thereof.
However, conventional (meth) acrylate compounds having a bulky alicyclic substituent are cumbersome in view of reaction conditions, resulting in poor yield, and the purification thereof is difficult. Thus, it is quite difficult to produce the conventional (meth)acrylate compounds on a commercial scale.
To solve the above problems, it is an object of the present invention to provide an acrylate compound having a bulky substituent which can be produced and purified by a simplified process to be suitable for commercial-scale production.
It is another object of the present invention to provide a method for producing the acrylate compound.
Accordingly, to achieve the first object, there is provided 8-alkyl-8-tricyclodecanyl (meth)acrylate represented by formula (1):
wherein R
is methyl or ethyl and R
is hydrogen or methyl.
To achieve the second object, there is provided a method of producing the compound including the steps of a) synthesizing 8-alkyl-8-tricyclodecanol by reacting tricyclodecan-8-one with either an alkyl Grignard reagent or an alkyl lithium reagent, and b) synthesizing 8-ethyl-8-tricyclodecanyl acrylate by reacting the 8-alkyl-8-tricyclodecanol synthesized in the step a) with (meth)acryloyl chloride.
Preferably, the Grignard reagent is either alkyl magnesium bromide or alkyl magnesium chloride.
More preferably, if the alkyl is ethyl, ethyl magnesium bromide or ethyl magnesium chloride is used as the Grignard reagent.
In the production method of the acrylate compound according to the present invention, a separation process may be performed after each step is completed. However, the separation process may be performed after all steps are performed in situ.

patent: 6153785 (2000-11-01), Jung
patent: 08240881 (1996-01-01), None


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