IP Library Granted Patent US 10,800,876
Granted Patent B2
US 10,800,876 · App. 15/312,594 · Granted Oct 13, 2020

Amine and non-amine derivatized polyaryletherketone random and block copolymers

Inventors: Ian David Henderson Towle (Oxfordshire, GB); Kaylie Jane Smith (Oxfordshire, GB); Pauline Julia Siddons (Oxfordshire, GB)
Assignee: Ketonex Limited
C08G61/127C08G65/4012C08G2261/12C08G2261/126C08G2261/1644C08G2261/3442C08G2261/45
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Quick Facts
Patent No.
US 10,800,876
App. No.
15/312,594
Granted
Oct 13, 2020
Kind
B2
Abstract

The present invention provides a method of preparing a polyaryletherketone copolymer (e.g. a random or block copolymer), said method comprising: polymerizing (i) a monomer system suitable for forming aryletherketone units and (ii) a comonomer in a reaction medium comprising: (a) a Lewis acid and (b) a controlling agent comprising an aromatic carboxylic acid, an aromatic sulphonic acid, or a derivative thereof; and polymers produced therefrom.

Claims (42)

1. A method of preparing particles of an amine-functionalised polyaryletherketone copolymer having an viscosity of at least 0.4 dl/g, said method comprising:

polymerizing, via an electrophilic process, (i) a monomer system suitable for forming aryletherketone units and comprising an acid halide and (ii) a comonomer system suitable for forming non-aryletherketone units which comprises moieties other than aryl, ether and ketone unit and an acid halide in a reaction medium comprising:

(a) a Lewis acid;

(b) a controlling agent comprising an aromatic carboxylic acid, an aromatic sulphonic acid, or a derivative thereof; and

(c) a capping agent comprising —NHL, —NRL or -NL 2 , wherein L is a leaving group selected from acetyl, haloacetyl, halosulphonyl and sulphonyl and R is an aliphatic or aromatic group,

wherein the polymerization takes place as a single step reaction in presence of the Lewis acid, the controlling agent and the capping agent in the reaction medium at a temperature from −50° C. to 150° C.,

wherein the comonomer does not comprise an imide group and/or a sulphone group.

2. The method of claim 1 , wherein said comonomer comprises an ester, imide, sulphone and/or amide group.

3. The method of claim 1 , wherein the polyaryletherketone copolymer is a block copolymer, and said monomer system suitable for forming the aryletherketone units is polymerized separately to the comonomer.

4. The method of claim 1 , wherein said comonomer comprises an ester, sulphone and/or amide group.

5. The method of claim 1 , wherein said aryletherketone unit does not comprise -Ph-O-Ph-C(═O)-Ph-O-Ph-C(═O)-Ph-C(═O)—.

6. The method of claim 1 , wherein said monomer system suitable for forming the aryletherketone units is polymerized separately to, or simultaneously with, the comonomer.

7. The method of claim 1 , wherein said aryletherketone units are independently selected from the group consisting of:

—Ar—O—Ar—C(═O)—,

—Ar—O—Ar—C(═O)—Ar—C(═O)—,

—Ar—O—Ar—O—Ar—C(═O)—,

—Ar—O—Ar—O—Ar—C(═O)—Ar—C(═O)—, and

—Ar—O—Ar—C(═O)—Ar—O—Ar—C(═O)—Ar—C(═O)—,

wherein each Ar is independently an aromatic moiety.

8. The method of claim 7 , wherein each Ar is independently selected from the group consisting of substituted or unsubstituted mononuclear aromatic moieties and substituted or unsubstituted polynuclear aromatic moieties.

9. The method of claim 1 , wherein said controlling agent is one or more of:

(i) Ar′(COOX) y ;

(ii) Ar′(SO 3 X) y ;

(iii) (Ar′COO − ) z M z+ ; or

(iv) (Ar′SO 3 − ) z M z+

wherein Ar′ is an aromatic group compatible with components remained in the reaction medium;

each X independently is a hydrogen atom or an organic group (R);

each y independently is 1, 2 or 3;

each M independently is a metal; and

each z independently is an integer equal to charge on the metal ion (M′).

10. The method of claim 1 , wherein said capping agent is represented by formula (Z) a —Ar—(X) b wherein:

each X is independently selected from the group consisting of —O—Ar, —C(═O)Cl, —C(═O)—Ar—O—Ar and —O—Ar—[—C(═O)—Ar—O—Ar—] c —H wherein each Ar is independently an aromatic moiety;

c is an integer,

Z is a protected amine group,

a is 1 to 5, and

b is 1 to 5.

11. The method of claim 10 , wherein each Z is independently selected from the group consisting of —NHL, —NRL and —NL 2 , and each L is a leaving group independently selected from the group consisting of acetyl, haloacetyl, sulphonyl, halosulphonyl, c is 1 to 10, each R is independently an aliphatic or aromatic group, a is 1, 2 or 3, and b is 1, 2 or 3.

12. The method of claim 1 , wherein said reaction medium comprises two or more types of comonomers.

13. The method of claim 1 , wherein the polyaryletherketone copolymer is an amine-functionalised polyaryletherketone copolymer, and said amine-functionalised polyaryletherketone copolymer is neither an amine-functionalised polyaryletherketone-imide copolymer nor an amine-functionalised polyaryletherketone-sulphone copolymer.

14. The method of claim 1 , wherein said —NL 2 is:

wherein Y is an aryl group, —(CH 2 ) n — or —(CF 2 ) n —, wherein n is an integer from 2 to 6.

15. The method of claim 1 , wherein said L is —SO 2 —CH 3 or —SO 2 —CF 3 .

Assignments (4)
SECURITY INTEREST Recorded Mar 13, 2026
From: OXFORD PERFORMANCE MATERIALS, INC.
To: KENSTON CAPITAL EMERGING TECHNOLOGY FUND I LP
Reel/Frame 074077/0347 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 27, 2022
From: KETONEX LTD.
To: OXFORD PERFORMANCE MATERIALS, INC
Reel/Frame 061559/0306 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 25, 2019
From: SIDDONS, PAULINE JULIA
To: KETONEX LIMITED
Reel/Frame 049860/0779 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 10, 2019
From: TOWLE, IAN DAVID HENDERSON; SMITH, KAYLIE JANE; SIDDONS, PAULINE JULIA
To: KETONEX LIMITED
Reel/Frame 049712/0138 →
Priority Claims (1)
GB 1409128.4 · May 22, 2014 · national
Continuity (1)
Related Publication 20170081467A1 · Mar 23, 2017