# US 5,347,044 A · Trans-beta-isocyanatoacrylate esters, their preparation, and polymers made therefrom

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- Number: US 5,347,044 A
- Document ID: US5347044A
- Status: Granted
- Kind: A
- Application number: 07/864,236
- Filed: 1992-04-06
- Granted: 1994-09-13
- Earliest claimed: 1992-04-06
- Assignees: The Curators of the University of Missouri
- Inventors: Thomas J. Byerley; Cecil C. Chappelow; J. David Eick
- Web page: https://patentgrep.com/patent/US5347044A

## CPC

- C07C 265/06: of an unsaturated carbon skeleton
- C08F 22/32: Alpha-cyano-acrylic acid; Esters thereof
- C07C 2601/14: The ring being saturated
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS

## Abstract

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.

## Claims

### Claim 1

A substantially pure compound comprising a trans-beta-isocyanatoacrylate ester in which an isocyanato functionality is directly linked to a beta-carbon in an acrylate portion of the compound, wherein said trans-beta-isocyanatoacrylate ester is iso-n-hexyl trans-beta-isocyanatoacrylate, cyclohexyl trans-beta-isocyanatoacrylate, benzyl trans-beta-isocyanatoacrylate, 2-methoxyethyl trans-beta-isocyanatoacrylate, 2-ethoxyethyl trans-beta-isocyanatoacrylate or 2-butoxyethyl trans-beta-isocyanatoacrylate.

### Claim 2 (depends on 1)

The compound of claim 1, wherein the trans-beta-isocyanatoacrylate ester is n-hexyl trans-beta-isocyanatoacrylate.

### Claim 3 (depends on 1)

The compound of claim 1, wherein the trans-beta-isocyanatoacrylate ester is cyclohexyl trans-beta-isocyanatoacrylate.

### Claim 4 (depends on 1)

The compound of claim 1, wherein the trans-beta-isocyanatoacrylate ester is benzyl trans-beta-isocyanatoacrylate.

### Claim 5 (depends on 1)

The compound of claim 1, wherein the trans-beta-isocyanatoacrylate ester is 2-methoxyethyl trans-beta-isocyanatoacrylate.

### Claim 6 (depends on 1)

The compound of claim 1, wherein the trans-beta-isocyanatoacrylate ester is 2-ethoxyethyl trans-beta-isocyanatoacrylate.

### Claim 7 (depends on 1)

The compound of claim 1, wherein the trans-beta-isocyanatoacrylate ester is 2-butoxyethyl trans-beta-isocyanatoacrylate.

### Claim 8

A substantially pure compound of the formula: ##STR5## wherein R is selected from the group consisting of C.sub.6 -C.sub.8 linear or branched alkyl; C.sub.5 -C.sub.6 cycloalkyl; aryl; alkaryl; aralkyl; C.sub.1 -C.sub.18 halogenated alkyl; halogenated aryl; C.sub.2 -C.sub.8 alkoxyalkyl; and alkoxyaryl.

### Claim 9 (depends on 8)

The compound of claim 8, wherein R is C.sub.6 linear alkyl.

### Claim 10 (depends on 8)

The compound of claim 8, wherein R is C.sub.6 branched alkyl.

### Claim 11 (depends on 8)

The compound of claim 8, wherein R is C.sub.7 linear alkyl.

### Claim 12 (depends on 8)

The compound of claim 8, wherein R is methoxyethyl.

### Claim 13 (depends on 8)

The compound of claim 8, wherein R is ethoxyethyl.

### Claim 14 (depends on 8)

The compound of claim 8, wherein R is butoxyethyl.