Phenylene ether oligomer, curable composition comprising the phenylene ether oligomer, and thermoset composition derived therefrom

Patent metadata

Field	Value
Publication number	US-10995182-B2
Application number	US-201916377935-A
Country	US
Kind code	B2
Filing date	Apr 8, 2019
Priority date	Apr 30, 2018
Publication date	May 4, 2021
Grant date	May 4, 2021

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.

First claim

What is claimed is:

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

wherein the phenylene ether oligomer comprises less than 0.1 weight percent of repeating units derived from a monohydric phenol having identical substituents in the 2- and 6-positions; and
wherein the phenylene ether oligomer comprises a vinyl benzene ether end group, an amine end group, maleimide end group, a norbornene group, an anhydride group, or a combination comprising at least one of the foregoing.

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

wherein
x and y are independently 0 to 30, provided that the sum of x and y is at least 2;
each occurrence of R 1 , R 2 , R 3 , and R 4 independently comprises hydrogen, halogen, unsubstituted or substituted C 1 -C 12 primary or secondary hydrocarbyl, C 1 -C 12 hydrocarbylthio, C 1 -C 12 hydrocarbyloxy, or C 2 -C 12 halohydrocarbyloxy wherein at least two carbon atoms separate the halogen and oxygen atoms;
z is 0 or 1;
Y has a structure comprising

wherein each occurrence of R 7 independently comprises hydrogen and C 1 -C 12 hydrocarbyl, and each occurrence of R 8 and R 9 is each independently hydrogen, C 1 -C 12 hydrocarbyl, or C 1 -C 6 hydrocarbylene wherein R 8 and R 9 collectively form a C 4 -C 12 alkylene group; and
R is independently at each occurrence a vinyl benzene ether end group, an amine end group, or a maleimide end group, a norbornene end group, or an anhydride group.

6. The phenylene ether oligomer of claim 5 , wherein each occurrence of R 1 and R 2 is methyl, each occurrence of R 3 and R 4 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 .

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 .

Assignees

• Sabic Global Technologies Bv
• Shpp Global Tech Bv

Inventors

• Tarkin-Tas Eylem
• Tas Huseyin

Classifications

• C08J2383/12

  containing polyether sequences · CPC title

• C08K7/14

  Glass · CPC title

• C08L71/12

  Polyphenylene oxides · CPC title

• C08L63/00

  Compositions of epoxy resins; Compositions of derivatives of epoxy resins · CPC title

• C07C39/17

  containing other rings in addition to the six-membered aromatic rings {, e.g. cyclohexylphenol} · CPC title