PHENYLENE ETHER OLIGOMER, CURABLE COMPOSITION COMPRISING THE PHENYLENE ETHER OLIGOMER, AND THERMOSET COMPOSITION DERIVED THEREFROM

• US 20190330424A1
• Filed: 04/08/2019
• Published: 10/31/2019
• Est. Priority Date: 04/30/2018
• Status: Active Grant

• Current Assignee: SHPP Global Technologies BV
• Original Assignee: SABIC Global Technologies BV (Government of Saudi Arabia)
• Inventors: Tarkin-Tas, Eylem, Tas, Huseyin
• Granted Patent: US 10,995,182 B2
• Time in Patent Office: Days
• CPC Class Codes: C07C 39/17 containing other rings in addition to the six-membered aromatic rings , e.g. cyclohexylphenol
• CPC Class Codes: C08G 65/00 Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
• CPC Class Codes: C08G 65/4087 characterised by the catalyst used
• CPC Class Codes: C08G 65/44 by oxidation of phenols
• CPC Class Codes: C08G 65/48 Polymers modified by chemical after-treatment
• CPC Class Codes: C08G 81/025 containing polyether sequences
• CPC Class Codes: C08L 63/00 Compositions of epoxy resins; Compositions of derivatives of epoxy resins
• CPC Class Codes: C08L 71/12 Polyphenylene oxides

Abstract

A phenylene ether oligomer has repeating units of the structure

and less than 30 weight percent of repeating units derived from a monohydric phenol having identical substituents in the 2- and 6-positions, wherein the phenylene ether oligomer includes a vinyl benzene ether end group, an amine end group, maleimide end group, a norbornene end group, an anhydride end group, or a combination comprising at least one of the foregoing. The phenylene ether oligomer can be used to provide a curable composition. The curable composition can be cured to provide a thermoset composition. Articles comprising the thermoset composition are also described.

Claims

1. A phenylene ether oligomer comprising repeating units of the structure

2. The phenylene ether oligomer of claim 1, wherein the phenylene ether oligomer has a number average molecular weight of 600 to 5,000 grams per mole, determined by gel permeation chromatography relative to polystyrene standards.

3. The phenylene ether oligomer of claim 1, wherein the phenylene ether oligomer has an intrinsic viscosity of less than 0.15 deciliter per gram, measured by Ubbelohde viscometer at 25°

C. in chloroform.

4. The phenylene ether oligomer of claim 1, wherein the phenylene ether oligomer comprises a vinyl benzene ether end group.

5. The phenylene ether oligomer of claim 1, wherein the phenylene ether oligomer is of the structure

6. The phenylene ether oligomer of claim 5, wherein each occurrence of R¹ and R² is methyl, each occurrence of R³ and R⁴ is hydrogen, Y is an isopropylidene group, and R is a vinyl benzyl ether group.

7. The phenylene ether oligomer of claim 1, wherein the phenylene ether oligomer comprises a polysiloxane block.

8. A method of making the phenylene ether oligomer of claim 1, the method comprising oxidatively polymerizing 2-methyl-6-cyclohexyl phenol in the presence of a catalyst to provide the phenylene ether oligomer.

9. The method of claim 8, further comprising reacting the phenylene ether oligomer with a vinyl benzene ether group, an amine group, a maleimide group, a norbornene group, an anhydride group, or a combination comprising at least one of the foregoing to provide a functionalized phenylene ether oligomer.

10. A curable composition comprising

the phenylene ether oligomer of claim 1;

and

a curing promoter.

11. The curable composition of claim 10, wherein the curing promoter comprises an amine, a dicyandiamide, a polyamide, an amidoamine, a Mannich base, an anhydride, a phenol-formaldehyde resin, a carboxylic acid functional polyester, a polysulfide, a polymercaptan, an isocyanate, a cyanate ester, or combinations thereof.

12. The curable composition of claim 10, further comprising an auxiliary curable resin, a curable unsaturated monomer composition, or both.

13. A thermoset composition comprising a cured product of the curable composition of claim 10, preferably wherein the thermoset composition has a glass transition temperature of greater than or equal to 180°

C.

14. An article comprising the thermoset composition of claim 13.

15. A method for the manufacture of a thermoset composition, the method comprising curing the curable composition of claim 10.