# US 9,040,636 B2 · Hydroxy ester resins

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- Number: US 9,040,636 B2
- Document ID: US9040636B2
- Status: Granted
- Kind: B2
- Application number: 14/357,380
- Filed: 2012-11-29
- Published: 2014-10-23
- Granted: 2015-05-26
- Earliest claimed: 2011-12-15
- Assignees: Dow Global Technologies LLC
- Applicants: Dow Global Technologies LLC
- Inventors: E. J. Campbell
- Web page: https://patentgrep.com/patent/US9040636B2

## CPC

- C08G 65/2615: {the other compounds containing carboxylic acid, ester or anhydride groups}
- C07C 67/26: with an oxirane ring
- C07C 69/54: Acrylic acid esters; Methacrylic acid esters
- C08F 22/20: Esters containing oxygen in addition to the carboxy oxygen
- C08G 59/22: Di-epoxy compounds
- C08K 5/10: Esters; Ether-esters
- C08L 67/02: Polyesters derived from dicarboxylic acids and dihydroxy compounds (C08L67/06 takes precedence)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)

## Abstract

A hydroxy ester resin composition such as a vinyl ester resin including the reaction product of (a) divinylarene dioxide resin; and (b) at least one ring opening reactant such as at least one monocarboxylic acid for example (meth)acrylic acid, in the presence of (c) at least one non-gelling catalyst such as a Lewis acid catalyst; a process for making the hydroxy ester resin composition; a curable hydroxy ester resin composition such as a curable resin composition made from the hydroxy ester resin composition; a process for curing the curable hydroxy ester resin composition; and a cured product made from the curable hydroxy ester resin composition. The cured product made from the above hydroxy ester resin composition is thermally stable and offers improved properties such as a lower viscosity and a high heat resistance compared to known cured products prepared from known epoxy resins.

## Claims

### Claim 1

A hydroxy ester resin comprising the reaction product of (a) at least one divinylarene dioxide, and (b) at least one monocarboxylic acid in the presence of (c) a non-gelling catalyst.

### Claim 2 (depends on 1)

The resin of claim 1, wherein the divinylarene dioxide is selected from the group comprising divinylbenzene dioxide, divinylnaphthalene dioxide, divinylbiphenyl dioxide, divinyldiphenylether dioxide, and mixtures thereof.

### Claim 3 (depends on 1)

The resin of claim 1, wherein the divinylarene dioxide comprises divinylbenzene dioxide; and wherein the concentration of said divinylbenzene dioxide ranges from about 0.5 weight percent to about 99.5 weight percent.

### Claim 4 (depends on 1)

The resin of claim 1, wherein the monocarboxylic acid comprises acrylic acid, methacrylic acid, cyanoacrylic acid, crotonic acid, alpha-phenylacrylic acid, methoxyacrylic acid, alpha-4-phenylphenylacrylic acid, monomethylester of maleic acid, monomethylester of fumaric acid,
or mixtures thereof.

### Claim 5 (depends on 1)

The resin of claim 1, wherein the equivalents of the carboxylic acid per equivalent of epoxide ranges from about 2 to about 0.1.

### Claim 6 (depends on 1)

The resin of claim 1, wherein the non-gelling catalyst comprises a Lewis acid catalyst, a hindered amine, a supported amine, or a mixture thereof.

### Claim 7 (depends on 6)

The resin of claim 6, wherein the Lewis acid catalyst comprises a triflate.

### Claim 8 (depends on 6)

The resin of claim 6, wherein the hindered amine or supported amine catalyst comprises 1,8-bis(dimethylamino)naphthalene; N′,N′,N′,N′-tetramethyl-1,8-naphthalenediamiine; polyvinyl pyridine; 2,6-di-tertbutylpyridine; or mixtures thereof.

### Claim 9 (depends on 1)

The resin of claim 1, including further an epoxy resin other than the at least one divinylarene dioxide component (a); wherein the epoxy resin comprises diglycidyl ether of bisphenol A, diglycidyl ether of bisphenol F, a cycloaliphatic epoxy resin, or mixtures thereof.

### Claim 10 (depends on 1)

A curable resin composition comprising (a) a hydroxy ester resin composition of claim 1; and (b) an initiator.

### Claim 11 (depends on 10)

A curable vinyl ester resin composition comprising (i) at least one hydroxy ester resin of claim 10; and (ii) at least one vinyl comonomer.

### Claim 12 (depends on 10)

The curable composition of claim 10, wherein the concentration of said the hydroxy ester resin ranges from about 0.1 weight percent to about 99.9 weight percent.

### Claim 13 (depends on 10)

The curable composition of claim 10, including further an inhibitor; wherein the concentration of the inhibitor ranges from about 0.01 weight percent to about 20 weight percent.

### Claim 14 (depends on 11)

The curable composition of claim 11, wherein the vinyl comonomer comprises styrene; alpha-methylstyrene; vinyl toluenes; halogenated styrenes; t-butylstyrenes; divinylbenzenes; the methyl, ethyl, isopropyl, butyl, or octyl esters of acrylic or methacrylic acid; multifunctional esters of ethylene glycol, glycerol, propylene glycol, 1,3-propanediol, butylene glycol, 1,4-butanediol, neopentylglycol, trimethylolpropane, pentaerythritol, or 1,6-hexanediol with acrylic or methacrylic acid; acrylic acid; methacrylic acid; crotonic acid; acrylamide; N-alkylacrylamides; diallylphthalate; triallylisocyanurate; diallylmaleate; dimethallylfumarate; or mixtures thereof.

### Claim 15

A process of preparing a hydroxy ester resin comprising reacting (a) at least one divinylarene dioxide, and (b) at least one monocarboxylic acid in the presence of (c) a non-gelling catalyst.

### Claim 16 (depends on 1)

A process of preparing a curable resin composition comprising admixing (a) a hydroxy ester resin composition of claim 1; and (b) an initiator.

### Claim 17

A process for preparing a vinyl ester resin comprising reacting (a) a divinylarene dioxide, and (b) the monocarboxylic acid; wherein the monocarboxylic acid comprises an acrylic acid, a (meth)acrylic acid, or mixtures thereof, in the presence of (c) a non-gelling catalyst to provide a vinyl ester resin composition.

### Claim 18 (depends on 1)

A process for preparing a curable vinyl ester resin composition comprising admixing (i) a hydroxy ester resin composition of claim 1; and (ii) at least one vinyl comonomer; and (iii) optionally, a polymerization inhibitor, or (iv) optionally, a polymerization initiator.

### Claim 19 (depends on 10)

An article made from the curable resin of claim 10.