&agr;, &ohgr;-methacrylate terminated macromonomer compounds

Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Mixing of two or more solid polymers; mixing of solid...

Reexamination Certificate

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Details

C433S228100, C523S120000, C523S401000, C523S443000, C523S444000, C525S533000, C525S922000

Reexamination Certificate

active

06353061

ABSTRACT:

The invention relates to compounds having repetitive units of &agr;,&ohgr;-methacrylate terminated macromonomer epoxide-carboxylic acid. Synthesis of such compounds is carried out by a two-step reaction or by simultaneous polymerization of diepoxides, dicarboxylic acids and unsaturated monocarboxylic acids. These compounds are useful as dental adhesives, dental cements, dental restoratives and dental luting materials.
&agr;,&ohgr;-methacrylate terminated epoxide-amine macromonomers recently described in patent application (DD 279667) are not comparable to the &agr;,&ohgr;-methacrylate epoxide-carboxylic acid macromonomers of the present invention. Nor is the synthesis of the &agr;,&ohgr;-methacrylate terminated epoxide carboxylic acid macromonomers of the present invention comparable to the synthesis of amine-macromonomers, because carboxylic acids react at higher temperatures with epoxides than do amines (see Houben-Weyl Bd 14/2, S. 499ff). At such high reaction temperatures there is concern that the polymerization of the unsaturated monocarboxylic acid may occur. M. Fedkte et al, in Plaste and Kautschuk 31 (1984) 405; K. Dusek, L. Matejka, Amer. Chem. Soc. 1984, 15, disclose reaction of epoxide-carboxylic acid to form insoluble network polymers caused by side reactions of epoxides and hydroxylic groups wherein R is an aromatic diepoxide moiety. The synthesis of &agr;,&ohgr;-methacrylate terminated epoxide carboxylic acid macromonomers in accordance with the present invention is surprising.
As used herein “(Meth)acrylic acid” is understood to mean acrylic and methacrylic acids.
BRIEF SUMMARY OF THE INVENTION
The invention provides &agr;,&ohgr;-methacrylate terminated epoxide-carboxylic acid macromonomer compounds formed by reaction of at least one diepoxide, at least one dicarboxylic acid and at least one unsaturated mono-carboxylic acid and having the general formula 1:
wherein R is an aromatic moiety formed from a diepoxide,
R′ is a substituted or unsubstituted aliphatic, araliphatic, cycloaliphatic or aromatic moiety formed from a dicarboxylic acid,
R′ is hydrogen, a substituted or unsubstituted aliphatic, araliphatic, aromatic or cycloaliphatic moiety formed from a mono-carboxylic acid, and n an integer from 1 to 20.


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