# US 12,180,337 B2 · Poly (phenylene ether) based compatibilizing material

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- Number: US 12,180,337 B2
- Document ID: US12180337B2
- Status: Granted
- Kind: B2
- Application number: 17/753,088
- Filed: 2020-08-20
- Published: 2022-09-01
- Granted: 2024-12-31
- Earliest claimed: 2019-08-20
- Assignees: Shpp Global Technologies B.V.
- Applicants: SHPP Global Technologies B.V.
- Inventors: Eylem Tarkin-Tas; Huseyin Tas; Nikhil Verghese
- Web page: https://patentgrep.com/patent/US12180337B2

## CPC

- C08G 65/48: Polymers modified by chemical after-treatment
- C08G 65/485: {Polyphenylene oxides}
- C03C 25/32: obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds
- C08L 71/00: Compositions of polyethers obtained by reactions forming an ether link in the main chain (of polyacetals C08L59/00; of epoxy resins C08L63/00; of polythioether-ethers C08L81/02; of polyether-sulfones C08L81/06); Compositions of derivatives of such polymers
- C08L 71/12: Polyphenylene oxides
- C03C 2213/00: Glass fibres or filaments
- C08G 2150/00: Compositions for coatings
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C03C: CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)

## Abstract

Compatibilizing materials for use with fibers and polymeric compositions are described. A compatibilizing material can include a silane (Si) modified polyphenylene ether (PPE) oligomer having a resin reactive functional group. The resin reactive functional group can be between the PPE moiety and a Si moiety. In other instances, the resin reactive functional group can be a substituent of the Si moiety.

## Claims

### Claim 1

A compatibilizing material comprising a silane (Si) modified polyphenylene ether (PPE) oligomer having a resin reactive functional group, wherein the resin reactive functional group is (1) a substituent of the PPE oligomer, (2) positioned between the PPE portion of the oligomer and the Si portion of the oligomer, (3) a substituent of the Si portion of the oligomer, or (4) a combination thereof;
wherein the compatibilizing material has the structure:
wherein A is the polyphenylene ether oligomer, a is 0 to 12, b is 0 to 12, R1 is a resin reactive group, R2 is a hydrogen (H), a substituted or unsubstituted hydrocarbyl group, R3 is a H, a substituted or unsubstituted hydrocarbyl group, or a substituted or unsubstituted alkoxy group, and R4 is a H, a substituted hydrocarbyl group, an unsubstituted hydrocarbyl group, a substituted aromatic group or an unsubstituted aromatic group; or R4 has the structure of:
wherein c is 0 to 12; d is 0 to 12; R5 is a resin reactive group; R6 is a H, a substituted or unsubstituted hydrocarbyl group; and R7 is a H, a substituted or unsubstituted hydrocarbyl group, or a substituted or unsubstituted alkoxy group; or
wherein the compatibilizing material has the structure:
wherein A is the polyphenylene ether oligomer, Y is a linking group comprising a resin reactive functional group R10; R2 is a H, a substituted or unsubstituted hydrocarbyl group; R3 and R8 are each independently a H, a substituted or unsubstituted hydrocarbyl group, or a substituted or unsubstituted alkoxy group; and R9 is a H, a substituted hydrocarbyl group or an unsubstituted hydrocarbyl group;
wherein the resin reactive group comprises an epoxy group, a substituted epoxy group, an olefin-containing group, a substituted olefin-containing group, an acrylate group, a substituted acrylate group, a cyano group, a substituted cyano group, a hydroxy group, or any combination thereof.

### Claim 2 (depends on 1)

The compatibilizing material of claim 1, wherein R9 is a substituted hydrocarbyl group or an unsubstituted hydrocarbyl group.

### Claim 3 (depends on 2)

The compatibilizing material of claim 2, wherein R9 is a substituted or unsubstituted aromatic group, or R9 has the structure of:
where Y is the linking group comprising the resin reactive functional group R10; R2 is a H, a substituted or unsubstituted hydrocarbyl group; and R3 and R8 are each independently a H, a substituted or unsubstituted hydrocarbyl group, or a substituted or unsubstituted alkoxy group.

### Claim 4 (depends on 1)

The compatibilizing material of claim 1, wherein the resin reactive group comprises an acrylate group, a substituted acrylate group, a hydroxy group, a vinyl group, or any combination thereof.

### Claim 5 (depends on 1)

The compatibilizing material of claim 1, wherein A comprises a poly (phenylene ether) having the chemical structure;
where Z1, Z2, Z3, and Z4 each independently is a hydrogen, a phenyl, a (bi) cyclic hydrocarbon, a unsubstituted or a substituted C1-C12 hydrocarbyl group provided that the hydrocarbyl group is not a tertiary hydrocarbyl, a C1-C12 hydrocarbylthio, a C1-C12 hydrocarbyloxy, or a C2-C12 halohydrocarbyloxy with at least two carbon atoms separating the halogen, and oxygen atoms, and z is at least 2;
or
where Q1, Q2, Q3, and Q4 each independently is a halogen, an unsubstituted or substituted C1-C12 primary or secondary hydrocarbyl, a C1-C12 hydrocarbylthio, a C1-C12 hydrocarbyloxy, and a C2-C12 halohydrocarbyloxy where at least two carbon atoms separate the halogen and oxygen atoms, x and y are independently 0 to 30, provided that the sum of x and y is at least 2; and L has the chemical structure:
where R15, R16, R17, and R18 are each independently is a hydrogen, an unsubstituted or substituted C1-C12 hydrocarbyl provided that the hydrocarbyl group is not a tertiary hydrocarbyl, a C1-C12 hydrocarbylthio, a C1-C12 hydrocarbyloxy, and a C2-C12 halohydrocarbyloxy with at least two carbon atoms separating the halogen and oxygen atoms; m is 0 or 1; and X has the chemical structure selected from the group
where R14 is a hydrogen or C1-C12 hydrocarbyl, R12 and R13 each independently is a hydrogen, a C1-C12 hydrocarbyl, or C1-C6 hydrocarbylene where R12 and R13 collectively can form a C4-C12 alkene, or a siloxane where R19 and R20 are each independently selected from hydrogen, hydrocarbyl or halogen-substituted hydrocarbyl, D is an integer of from about 30 to about 70.

### Claim 6 (depends on 5)

The compatibilizing material of claim 5, having the structure of
where: a and c are each independently 0 to 12; b and d are each independently 0 to 12; and R2 and R6 are each independently a H, a substituted or unsubstituted hydrocarbyl group; R3 and R7 are each independently a H, a substituted or unsubstituted hydrocarbyl group, or a substituted or unsubstituted alkoxy group; and x and y are independently 0 to 30, provided that the sum of x and y is at least 2;
where: a and c are each independently 0 to 12; b and d are each independently 0 to 12; and R2 and R6 are each independently a H, a substituted or unsubstituted hydrocarbyl group; R3 and R7 are each independently a H, a substituted or unsubstituted hydrocarbyl group, or a substituted or unsubstituted alkoxy group; x and z are independently 0 to 30, provided that the sum of x and z is at least 2 and y is 0 or 1;
where k is 1 to 10, x and, z are independently 0 to 40, y is 0 or 1, wherein when y is 0, at least one of x and z is 1 to 40, R2 is a H, a substituted or unsubstituted hydrocarbyl group, and R3 and R8 each independently is a H, a substituted or unsubstituted hydrocarbyl group, or a substituted or unsubstituted alkoxy group;
where k is 1 to 10, x and, z are independently 0 to 40, y is 0 or 1, wherein when y is 0, at least one of x and z is 2 to 40, R2 is a H, a substituted or unsubstituted hydrocarbyl group, and R3 and R8 each independently is a H, a substituted or unsubstituted hydrocarbyl group, or a substituted or unsubstituted alkoxy group;
or
where R22 and R23 each independently is a hydrocarbyl or substituted hydrocarbyl group, R24 and R25 each independently is an epoxy group, a substituted epoxy group, an olefin-containing group, a substituted olefin-containing group, an acrylate group, a substituted acrylate group, a cyano group, a substituted cyano group, a cyanate group a hydroxy group, or any combination thereof, i is 0 to 6 and j is 0 to 6, x and z are independently 0 to 30, provided that the sum of x and z is at least 2 and y is 0 or 1.

### Claim 7

A compatibilizing material, having the structure of
where, and R2 is H, a substituted or unsubstituted hydrocarbyl group, R3 is a H, a substituted or unsubstituted hydrocarbyl group, or a substituted or unsubstituted alkoxy group, a is 0 to 12, b is 0 to 12, and z is 2 to 30;
where k is 1 to 10, z is 1 to 40, R2 is H, a substituted or unsubstituted hydrocarbyl group, and R3 and R8 each independently is a H, a substituted or unsubstituted hydrocarbyl group, or a substituted or unsubstituted alkoxy group;
or
where R22 and R23 each independently is a hydrocarbyl or substituted hydrocarbyl group, R is an epoxy group, a substituted epoxy group, an olefin-containing group, a substituted olefin-containing group, an acrylate group, a substituted acrylate group, a cyano group, a substituted cyano group, a cyanate group a hydroxy group, or any combination thereof, i is 0 to 6 and j is 0 to 6, and z is 1 to 30.

### Claim 8 (depends on 1)

A surface treated material and/or a coated material comprising the compatibilizing material of claim 1.

### Claim 9 (depends on 1)

A surface treated material and/or a coated material, wherein a surface of the material is treated or coated with the compatibilizing material of claim 1.

### Claim 10 (depends on 8)

A thermosetting resin composition comprising the surface treated material and/or coated material of claim 8.

### Claim 11 (depends on 1)

A thermosetting resin composition comprising the compatibilizing material of claim 1 and a glass fiber, alumina fiber, basalt fiber, quartz fiber, inorganic filler or metal foil.

### Claim 12 (depends on 1)

A sized fiber comprising the compatibilizing material of claim 1.

### Claim 13 (depends on 12)

The sized fiber of claim 12, wherein a least a portion of the compatibilizing material is attached to a polymeric resin and the sized fiber.

### Claim 14 (depends on 13)

The sized fiber of claim 13 wherein the polymeric resin comprises a thermoset polymer, a thermoplastic polymer, a fire-retardant resin composition, or any combination thereof.

### Claim 15 (depends on 8)

An article of manufacture comprising a sized fiber and the surface treated material and/or the coated material of claim 8.

### Claim 16 (depends on 1)

The compatibilizing material of claim 1, having the structure:
wherein R4 is a substituted or unsubstituted aromatic group.