# US 2014/0155563 A1 · High performance acrylamide adhesives

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- Number: US 2014/0155563 A1
- Document ID: US20140155563A1
- Status: Published application
- Kind: A1
- Application number: 13/980,535
- Filed: 2012-12-04
- Published: 2014-06-05
- Earliest claimed: 2012-12-04
- Assignees: Empire Technology Development LLC
- Applicants: Empire Technology Development LLC
- Inventors: William B. Carlson; Gregory D. Phelan
- Web page: https://patentgrep.com/patent/US20140155563A1

## CPC

- C08F 220/58: containing oxygen in addition to the carbonamido oxygen {, e.g. N-methylolacrylamide, N-(meth)acryloylmorpholine}
- C07H 13/04: having the esterifying carboxyl radicals attached to acyclic carbon atoms
- C07H 15/04: attached to an oxygen atom of the saccharide radical
- C08F 222/385: {Monomers containing two or more (meth)acrylamide groups, e.g. N,N'-methylenebisacrylamide}
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C07H: SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS (derivatives of aldonic or saccharic acids C07C, C07D; aldonic acids, saccharic acids C07C59/105, C07C59/285; cyanohydrins C07C255/16; glycals C07D; compounds of unknown constitution C07G; polysaccharides, derivatives thereof C08B; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; sugar industry C13)

## Abstract

Disclosed are derivatives of (tetrahydropyranyl)methyl acrylamide and polymers derived therefrom, as well as methods of making such compounds and polymers. Adhesives, coatings, and plastics which include such polymers are also described.

## Claims

### Claim 1

A compound of Formula I:
and stereoisomers thereof, wherein
Y is —C(H)(R3)— or —C(H)(R3)—C(H)(R4)—;
R1, R2, R3, and R4 are independently an —OH, a protected hydroxyl group, or a group of Formula II:
provided that not more than one of R1, R2, R3, and R4 is a group of Formula II; and
R5, R6, R7 and R8 are independently selected from hydrogen and a substituted or unsubstituted alkyl group.

### Claim 2 (depends on 1)

The compound of claim 1 wherein the protected hydroxyl group is selected from trimethylsilyl, t-butyldimethylsilyl, acetyl, benzyl, benzoyl, or methoxymethyl.

### Claim 3 (depends on 1)

The compound of claim 1 wherein R5 and R6 are independently selected from the group consisting of H and a methyl group.

### Claim 4 (depends on 1)

The compound of claim 1 wherein R7 and R8 are independently selected from the group consisting of H, a methyl group and an ethyl group.

### Claim 5 (depends on 1)

The compound of claim 1 having Formula IA:

### Claim 6 (depends on 1)

The compound of claim 1 selected from
N-((3,4,5,6-tetrahydroxytetrahydro-2H-pyran-2-yl)methyl)acrylamide or
N-((3,4,5,6-tetrahydroxytetrahydro-2H-pyran-2-yl)methyl)methacrylamide.

### Claim 7 (depends on 1)

The compound of claim 1 wherein one of R1, R2, R3, and R4 is the group of Formula II.

### Claim 8 (depends on 1)

The compound of claim 1 having Formula IB:

### Claim 9 (depends on 1)

The compound of claim 1 selected from
N-((3,4,6-trihydroxy-5-methacrylamidotetrahydro-2H-pyran-2-yl)methyl)methacrylamide,
N-((5-acrylamido-3,4,6-trihydroxytetrahydro-2H-pyran-2-yl)methyl)methacrylamide,
N-(6-(acrylamidomethyl)-2,4,5-trihydroxytetrahydro-2H-pyran-3-yl)methacrylamide, or
N-((5-acrylamido-3,4,6-trihydroxytetrahydro-2H-pyran-2-yl)methyl)acrylamide.

### Claim 10

A polymer comprising one or more repeating units derived from the compound of Formula I:
and stereoisomers thereof, wherein
Y is —C(H)(R3)— or —C(H)(R3)—C(H)(R4)—;
R1, R2, R3, and R4 are independently an —OH, a protected hydroxyl group, or a group of Formula II:
provided that not more than one of R1, R2, R3, and R4 is a group of Formula II; and
R5, R6, R7 and R8 are independently selected from the group consisting of hydrogen and a substituted or unsubstituted alkyl group.

### Claim 11 (depends on 10)

The compound of claim 10 wherein R5 and R6 are independently selected from the group consisting of H and a methyl group.

### Claim 12 (depends on 10)

The compound of claim 10 wherein R7 and R8 are independently selected from the group consisting of H, a methyl group and an ethyl group.

### Claim 13 (depends on 10)

The polymer of claim 10 wherein one of R1, R2, R3, and R4 is a group of Formula II.

### Claim 14 (depends on 10)

The polymer of claim 10 wherein the one or more repeating units are derived from the compound of Formula IA, IB or both IA and IB:

### Claim 15 (depends on 10)

The polymer of claim 10 wherein the one or more repeating units are derived from one or more compounds selected from
N-((3,4,5,6-tetrahydroxytetrahydro-2H-pyran-2-yl)methyl)acrylamide,
N-((3,4,5,6-tetrahydroxytetrahydro-2H-pyran-2-yl)methyl)methacrylamide,
N-((3,4,6-trihydroxy-5-methacrylamidotetrahydro-2H-pyran-2-yl)methyl)methacrylamide,
N-((5-acrylamido-3,4,6-trihydroxytetrahydro-2H-pyran-2-yl)methyl)methacrylamide,
N-(6-(acrylamidomethyl)-2,4,5-trihydroxytetrahydro-2H-pyran-3-yl)methacrylamide, or
N-((5-acrylamido-3,4,6-trihydroxytetrahydro-2H-pyran-2-yl)methyl)acrylamide.

### Claim 16 (depends on 10)

The polymer of claim 10 comprising from 2 to about 1,000,000 repeating units derived from the compound of Formula I.

### Claim 17 (depends on 10)

The polymer of claim 10 selected from a polyacrylamide, a polyacrylate, a polyvinyl, an epoxy, a polyurea, a polyurethane, an alkyd resin, or a copolymer of any of the foregoing.

### Claim 18

A method of making a compound of Formula I comprising:
contacting a compound of Formula III,
with a compound of Formula IV,
optionally in the presence of a base, wherein
R is hydrogen or a substituted or unsubstituted alkyl group;
Y is —C(H)(R3)— or —C(H)(R3)—C(H)(R4)—;
R1, R2, R3, and R4 are independently an —OH, a protected hydroxyl group, or an —NHR8 wherein R8 is hydrogen or a substituted or unsubstituted alkyl group, provided that not more than one of R1, R2, R3, and R4 is an —NHR8;
R7 is hydrogen or a substituted or unsubstituted alkyl group; and
LG is a leaving group.

### Claim 19 (depends on 18)

The method of claim 18 wherein the protected hydroxyl group is selected from trimethylsilyl, t-butyldimethylsilyl, acetyl, benzyl, benzoyl, or methoxymethyl.

### Claim 20 (depends on 18)

The method of claim 18 wherein R7 and R8 are hydrogen.

### Claim 21 (depends on 18)

The method of claim 18 wherein LG is chloride, and the base is selected from pyridine, dimethylaminopyridine, triethylamine, diisopropylethylamine or a mixture of any two or more thereof.

### Claim at position 22

-27. (canceled)