# US 2014/0155558 A1 · Oxazolidone ring containing vinyl ester resin and products therefrom

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- Number: US 2014/0155558 A1
- Document ID: US20140155558A1
- Status: Published application
- Kind: A1
- Application number: 14/232,975
- Filed: 2011-08-01
- Published: 2014-06-05
- Earliest claimed: 2011-08-01
- Assignees: Dow Global Technologies LLC
- Inventors: Joseph Gan; Patrick P. Yan; Yan L. Feng; Wayne Y. Zhang
- Web page: https://patentgrep.com/patent/US20140155558A1

## CPC

- C08G 59/1466: {Acrylic or methacrylic acids}
- C08F 26/02: by a single or double bond to nitrogen
- C08G 59/1455: {Monocarboxylic acids, anhydrides, halides, or low-molecular-weight esters thereof}
- C08G 59/1461: {Unsaturated monoacids}
- C08G 73/06: Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08L 63/04: Epoxynovolacs
- C08L 63/10: Epoxy resins modified by unsaturated compounds
- C08F 212/08: Styrene
- C08F 220/06: Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)

## Abstract

A process comprising contacting a) an epoxy resin; b) an adduct comprising at least one oxazolidone ring prepared from a multifunctional epoxy resin and an isocyanate compound; and c) an unsaturated acid to form a vinyl ester, is disclosed.

## Claims

### Claim 1

A process comprising:
contacting
a) an epoxy resin wherein the epoxy resin is selected from the group consisting of phenol novolac epoxy resins, cresol novolac epoxy resins, bis-phenol A novolac epoxy resins, bisphenol-A novolac epoxy resins, tris-epoxy resins, epoxidized tetrafunctional phenol ethane, epoxidized cyclohexane tetraphenol, dicyclopentadiene epoxy resins, and mixtures thereof;
b) an adduct comprising at least one oxazolidone ring prepared from a multifunctional epoxy resin and an isocyanate compound; and
c) an unsaturated acid
to form a vinyl ester.

### Claim 2

(canceled)

### Claim 3 (depends on 1)

The process of claim 1 wherein the multifunctional epoxy resin is selected from the group consisting of phenol novolac epoxy resins, cresol-novolac epoxy resins, bisphenol-A novolac epoxy resins, epoxidized tetrafunctional phenol ethane, epoxidized cyclohexane tetraphenol, trisepoxy resins, polyfunctional epoxy resins, naphthalene epoxy resins, divinylbenzene, dicyclopentadiene-type epoxy resins, phosphorous containing epoxy resins, multi aromatic epoxy resins, and mixtures thereof.

### Claim 4 (depends on 1)

The process of claim 1, wherein the multifunctional epoxy resin comprises an epoxy resin having a functionality of at more than 2.1 and an EEW of from 100 to 300.

### Claim 5 (depends on 1)

The process of claim 1 wherein the isocyanate compound has an isocyanate group of 2 or more and an IEW of from 100 to 500.

### Claim 6 (depends on 1)

The process of claim 1 wherein the isocyanate compound is a polymeric isocyanate compound.

### Claim 7 (depends on 1)

The process of claim 1, wherein the unsaturated acid is selected from the group consisting of acrylic acid, methacrylic acid, cinnamic acid, crotonic acid, sorbic acid, monomethyl maleate, monobutyl maleate, half esters of unsaturated dibasic acids, and combinations thereof.

### Claim 8 (depends on 1)

The process of claim 1 wherein the adduct further comprises a catalyst.

### Claim 9 (depends on 8)

The process of claim 8 wherein the catalyst is selected from the group consisting of a phosphonium compound, an ammonium compound, chromium salts, amino compounds and combinations thereof.

### Claim 10 (depends on 1)

The process of claim 1 wherein the multifunctional epoxy resin is selected from the group consisting of phenol novolac epoxy resins, cresol-novolac epoxy resins, polyfunctional epoxy resins, naphthalene epoxy resins, dicyclopentadiene-type epoxy resins, phosphorous containing epoxy resins, multi-aromatic epoxy resins and combinations thereof.

### Claim 11 (depends on 1)

The process of claim 1, wherein the adduct is present in a range of from about 0.1 weight percent to about 100 weight percent, and the unsaturated acid is present in a range of from about 1 weight percent to about 60 weight percent.

### Claim 12 (depends on 1)

The vinyl ester formed by the process of claim 1.

### Claim 13 (depends on 12)

The vinyl ester of claim 12, represented by the formula
wherein
R1 is selected from the group consisting of a phenyl ring structure, a polymeric phenyl ring structure and derivatives thereof;
R2 is selected from the group consisting of a phenoxy ring structure, a polymeric phenoxy ring structure and derivatives thereof;
R is selected from the group consisting of a hydrogen group, an alkyl group, an alkoxy group, a phenyl ring structure, a polymeric phenyl ring structure derivatives of phenyl ring structures, derivatives of polymeric phenyl ring structures, a phenoxy ring structure, a polymeric phenoxy ring structure derivatives of phenoxy ring structures, and derivatives of polymeric phenoxy ring structures;
x is an integer between 0 and 5;
y is an integer of at least 1; and
z is an integer between 0 and 5.

### Claim 14 (depends on 1)

The process of claim 1 further comprising:
d) contacting the vinyl ester with a vinyl monomer.

### Claim 15 (depends on 14)

The process of claim 14 wherein the vinyl monomer is selected from the group consisting of styrene, ring-chlorinated styrenes, alkylated styrenes, alkenylated styrenes, vinyl esters of carboxylic acids with 2-6 carbon atoms per molecule, acrylic and methacrylic acid esters without functional groups, allyl compounds and combinations thereof.