University of Missouri

Midwest Research Institute

Conmaco, Inc.

Thomas J Byerley

Cecil C Chappelow

J David Eick

James F Engel

Howard W Christie

Cecil C Chappelow, Jr

Copolymer compositions are provided, including those which undergo less than .+-.1.0% bulk polymerization shrinkage and are useful as strain-free composites, high-strength adhesives, and precision castings. The copolymer compositions are formed from the cationic initiated polymerization of alicyclic spiroorthocarbonate monomers and epoxy resin monomers or comonomers. A preferred spiroorthocarbonate monomer is 2,3,8,9-di(tetramethylene)-1,5,7,11-tetraoxaspiro-[5,5]undecane. A preferred epoxy resin is a three component epoxy comonomer mixture of (i) diglycidyl ether of bisphenol A, (ii) 3,4-epoxycyclohexanemethyl-3,4-epoxycyclohexane carboxylate, and (iii) vinyl cyclohexene dioxide, preferably in a ratio of 5:4:1 by weight.

Polymeric compositions and composites prepared from spiroorthocarbonates

Polymeric compositions and composites prepared from

Compounds are described which are S-(.omega.-hydroxyalkyl) esters of thioacrylic and thiomethacrylic acids. The compounds have the formula: ##STR1## wherein: R is hydrogen or methyl; and

S-(.omega.-hydroxyalkyl) esters of thioacrylic and thiomethacrylic acids

Novel trans-beta-isocyanatoacrylate esters, their preparation and use in forming novel polymeric compositions, including polymers useful as adhesives, are disclosed. The trans-beta-isocyanatoacrylate esters have the formula: ##STR1## wherein R is C.sub.1 -C.sub.18 linear or branched alkyls; C.sub.5 -C.sub.6 cycloalkyl; aryl; alkaryl; aralkyl; C.sub.1 -C.sub.18 halogenated alkyl; halogenated aryl; C.sub.1 -C.sub.8 alkoxyalkyl; or alkoxyaryl.

Trans-beta-isocyanatoacrylate esters, their preparation, and polymers

.alpha.-Substituted acrylic acid esters, their polymers and adhesives therefrom, and methods of synthesizing these compounds. The compounds of the invention are useful as intermediates in the synthesis of isocyanato esters and can be polymerized to form an effective, non-toxic adhesive. The method of the invention encompasses utilizing the adhesive composition in biomedical applications, such as joining live animal tissue. Other adhesive applications are contemplated for living tissue and inanimate objects. The compounds are also used as monomers which can be polymerized, used in conjunction with other monomers as adhesive compositions, cross-linking agents, dye acceptor additives to vinylic polymers and useful chemical intermediates. The method of the invention encompasses synthesizing the aforementioned monomers and intermediates. Methyl .alpha.-(ethoxycarbonamido)acrylate is synthesized from either DL-serine or methyl pyruvate. For use as an intermediate, silyl substitution of the compound is accomplished by reacting the ester with trimethylchlorosilane. This .alpha.-substituted silated ester is used as an intermediate in the preparation of methyl .alpha.-isocyanatoacrylate, which can be polymerized with N-vinyl-2-pyrrolidone to produce a desirable adhesive. Analagous procedures, starting with L-ethyl serine and L-benzyl serine, respectively, are followed to arrive at the corresponding ethyl and benzyl esters.

.alpha.-substituted acrylic acid esters, their polymers and method of

.alpha.-Substituted acrylic acid esters, their polymers and adhesives therefrom, and methods of synthesizing these compounds. The compounds of the invention are useful as intermediates in the synthesis of isocyanato esters and can be polymerized to form an effective, non-toxic adhesive. The method of the invention encompasses utilizing the adhesive composition in biomedical applications, such as joining live animal tissue. Other adhesive applications are contemplated for living tissue and inanimate objects. The compounds are also used as monomers which can be polymerized, used in conjunction with other monomers as adhesive compositions, cross-linking agents, dye acceptor additives to vinylic polymers and useful chemical intermediates. The method of the invention encompasses synthesizing the aformentioned monomers and intermediates. Methyl .alpha.-(ethoxycarbonamido)acrylate is synthesized from either DL-serine or methyl pyruvate. For use as an intermediate, silyl substitution of the compound is accomplished by reacting the ester with trimethylchlorosilane. This .alpha.-substituted silated ester is used as an intermediate in the preparation of methyl .alpha.-isocyanatoacrylate, which can be polymerized with N-vinyl-2-pyrrolidone to produce a desirable adhesive. Analagous procedures, starting with L-ethyl serine and L-benzyl serine, respectively, are followed to arrive at the corresponding ethyl and benzyl esters.

.alpha.-substituted acrylic acid esters

An improved pile driving cap block cushion material is the subject of this invention. The material is a thermoplastic material characterized by being in particulate form, fiber filled (preferably glass fiber filled), having a melting point of 125.degree. C. or higher, a secant modulus of elasticity of from 50,000 to 800,000 p.s.i. and a coefficient of restitution of from 0.4 to 0.9. A number of thermoplastic materials are suitable for forming the material of the invention and include polyamides, polyesters, polyolefins, polycarbonates, polyimides, polyamide-imide copolymers, acetal homopolymers, acetal copolymers, fluoroplastics, polyphenyl oxides, copolyesters, polyetherimides, polystyrenes, polyvinyls, and polysulfones. A particularly useful group of materials is poly(ethylene terephthalate), poly(butylene terephthalate), nylon 6 and nylon 66. Additives such as antioxidants, heat stabilizers, reinforcers and colorants may also be added.

Pile driving cap block cushion assembly

An improved pile driving cap block cushion is the subject of this invention. The material is a glass filled thermoplastic characterized by a melting point of 125.degree. C. or higher, a secant modulus of elasticity of from 50,000 to 800,000 p.s.i. and a coefficient of restitution of from 0.4 to 0.9. A number of thermoplastics are suitable for forming the material of the invention and include polyamides, polyesters, polyolefins, polycarbonates, polyimides, polyamide-imide copolymers, acetal homopolymers, acetal copolymers, fluoroplastics, polyphenyl oxides, copolyesters, polyetherimides, polystyrenes, polyvinyls, and polysulfones. A particularly useful group of materials is poly(ethylene terephthalate), poly(butylene terephthalate) nylon 6 and nylon 66. Additives such as antioxidants, heat stabilizers, reinforcers and colorants may also be added.

Growing community of inventors

Mission, KS, United States of America

Thomas J Byerley