# US 11,078,329 B2 · Functional phenylene ether oligomer, curable and thermoset compositions prepared therefrom

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 11,078,329 B2
- Document ID: US11078329B2
- Status: Granted
- Kind: B2
- Application number: 16/392,871
- Filed: 2019-04-24
- Published: 2019-11-07
- Granted: 2021-08-03
- Earliest claimed: 2018-05-07
- Assignees: Shpp Global Technologies B.V.
- Applicants: Sabic Global Technologies B.V.
- Inventors: Lohith Kenchaiah; Rajesh Chowdhury; Gurunath Pozhal Vengu; Gaurav Mediratta; Ranjith Choorikkat
- Web page: https://patentgrep.com/patent/US11078329B2

## CPC

- C08G 65/48: Polymers modified by chemical after-treatment
- C08G 65/485: {Polyphenylene oxides}
- B29C 45/0001: {characterised by the choice of material}
- B29K 2071/12: {PPO, i.e. polyphenylene oxide; PPE, i.e. polyphenylene ether}
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- B29C: SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING (making preforms B29B11/00; making laminated products by combining previously unconnected layers which become one product whose layers will remain together B32B37/00 - B32B41/00)
- B29K: INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR {MOULDS, } REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS

## Abstract

A functional phenylene ether oligomer of the structure wherein Q1, Q2, Q3, Q4, x, y, and R are as defined herein. A curable composition includes the functional phenylene ether oligomer, and a thermoset composition includes a cured product derived from the curable composition.

## Claims

### Claim 1

A functional phenylene ether oligomer of the structure
wherein
Q1 and Q2 are each independently halogen, unsubstituted or substituted C1-12 primary or secondary hydrocarbyl, C1-12 hydrocarbylthio, C1-12 hydrocarbyloxy, or C2-12 halohydrocarbyloxy wherein at least two carbon atoms separate the halogen and oxygen atoms;
Q3 and Q4 are each independently hydrogen, halogen, unsubstituted or substituted C1-12 primary or secondary hydrocarbyl, C1-12 hydrocarbylthio, C1-12 hydrocarbyloxy, or C2-12 halohydrocarbyloxy wherein at least two carbon atoms separate the halogen and oxygen atoms;
Q5, Q6 and Q7 are each independently halogen, unsubstituted or substituted C1-12 primary or secondary hydrocarbyl, C1-12 hydrocarbylthio, C1-12 hydrocarbyloxy, or C2-12 halohydrocarbyloxy wherein at least two carbon atoms separate the halogen and oxygen atoms, preferably wherein Q5, Q6 and Q7 are each methyl;
x and y are each independently 0-30, provided that the sum of x and y is at least 2; and
R is independently at each occurrence a group containing unsaturation, an epoxy, a benzoxazine, an isocyanate, a cyanate ester, a melamine, a cyanophenyl, a maleimide, a phthalonitrile, a cycloalkylphenyl, an ethoxylate, a urethane, an anhydride, or an allylhydroxypropyl.

### Claim 2 (depends on 1)

The functional phenylene ether oligomer of claim 1, wherein each occurrence of R is independently a vinyl benzyl group, an allyl group, a nitrile group, an acrylate group, or a methacrylate group.

### Claim 3 (depends on 1)

The functional oligomer of claim 1, wherein the oligomer has an intrinsic viscosity of 0.04-0.2 deciliter per gram.

### Claim 4 (depends on 1)

The functional oligomer of claim 1, wherein the oligomer has a number average molecular weight of 600-4,500 grams per mole, determined by gel permeation chromatography relative to polystyrene standards in chloroform.

### Claim 5 (depends on 1)

The functional phenylene ether oligomer of claim 1, wherein each occurrence of Q5, Q6 and Q7 are methyl and the phenylene ether oligomer is of the structure
wherein Q1, Q2, Q3, Q4, R, x and y are as defined in claim 1.

### Claim 6 (depends on 1)

The functional phenylene ether oligomer of claim 1, wherein each occurrence of Q1Q2, Q5, Q6 and Q7 are methyl and each occurrence of Q3 and Q4 are hydrogen and the phenylene ether oligomer is of the structure
wherein R, x and y are as defined in claim 1.

### Claim 7 (depends on 1)

A method of making the functional phenylene ether oligomer of claim 1, the method comprising
oxidatively polymerizing a monohydric phenol in the presence of a catalyst and trisubstituted resorcinol to provide a phenylene ether oligomer; and
combining the phenylene ether oligomer with a compound comprising unsaturation, an epoxy, a benzoxazine, an isocyanate, a cyanate ester, a melamine, a cyanophenyl, a maleimide, a phthalonitrile, a cycloalkylphenyl, an ethoxylate, a urethane, an anhydride, or an allylhydroxypropyl to provide the functional phenylene ether oligomer.

### Claim 8 (depends on 1)

A curable composition comprising
the functional phenylene ether oligomer of claim 1; and
a curing promoter.

### Claim 9 (depends on 8)

The curable composition of claim 8, further comprising an auxiliary curable resin, a curable unsaturated monomer composition, or both.

### Claim 10 (depends on 8)

A thermoset composition comprising a cured product of the composition of claim 8.

### Claim 11 (depends on 10)

The thermoset composition of claim 10, having a glass transition temperature of greater than or equal to 180° C.

### Claim 12 (depends on 10)

An article comprising the thermoset composition of claim 10.

### Claim 13 (depends on 12)

The article of claim 12, wherein the article is in the form of a composite, a foam, a fiber, a layer, a coating, an encapsulant, an adhesive, a sealant, a molded component, a prepreg, a casing, or a combination comprising at least one of the foregoing.

### Claim 14 (depends on 8)

A method for the manufacture of a thermoset composition, the method comprising curing the curable composition of claim 8.

### Claim 15 (depends on 14)

The method of claim 14, wherein the curing comprises injecting the curable composition into a mold, and curing the injected composition at 150-250° C. in the mold.