IP Library Granted Patent US 10,100,144
Granted Patent B2
US 10,100,144 · App. 15/312,395 · Granted Oct 16, 2018

Method for making particulate amine-functionalized polyaryletherketone polymers and copolymers thereof

Inventors: Ian David Henderson Towle (Oxfordshire, GB); Kaylie Jane Smith (Oxfordshire, GB)
Assignee: Ketonex Limited
C08G61/127C08G2261/122C08G2261/126C08G2261/1644C08G2261/3442C08G2261/3444C08G2261/45
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Quick Facts
Patent No.
US 10,100,144
App. No.
15/312,395
Granted
Oct 16, 2018
Kind
B2
Abstract

The present invention provides a method of preparing an amine-functionalized (e.g. amine-terminated) polyaryletherketone polymer, or imide- or sulphone-copolymer thereof and amine-protected analogs thereof, said method comprising the step of polymerizing a monomer system in a reaction medium comprising a capping agent comprising —NR 2 , —NRH or a protected amine group.

Claims (54)

1. A method of preparing an amine-functionalized polyaryletherketone polymer, an imide- or sulphone-copolymer thereof or an amine-protected analogues thereof,

said method comprising:

polymerizing a monomer system in a reaction medium comprising a Lewis acid, a controlling agent and a capping agent comprising —NR 2 , —NRH or a protected amine group,

wherein each R is independently an aliphatic group or an aromatic group.

2. The method of claim 1 , wherein said controlling agent comprises an aromatic carboxylic acid, an aromatic sulphonic acid, or a derivative thereof.

3. The method of claim 1 , wherein said controlling agent comprises a Lewis base.

4. The method of claim 1 , wherein said monomer system comprises an imide and/or sulphone monomer.

5. The method of claim 1 , wherein said capping agent is an agent 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 group;

c is an integer;

Z is a protected amine group;

a is 1 to 5; and

b is 1 to 5.

6. 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 the remaining components of 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 ion, and

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

7. The method of claim 1 , wherein said polyaryletherketone is a homopolymer or copolymer of one or more of the following repeat units:

—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)—

—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 and unsubstituted mononuclear aromatic moieties and substituted and unsubstituted polynuclear aromatic moieties.

9. The method of claim 7 , wherein Ar is phenylene.

10. The method of claim 1 , wherein said polyaryletherketone is a homopolymer.

11. The method of claim 1 , wherein said polymer is PEKK or an imide or sulphone copolymer thereof.

12. The method of claim 1 , wherein the Lewis acid is added to the reaction medium prior to the controlling agent.

13. The method of claim 12 , wherein the components are added to the reaction medium in the following order:

(i) the Lewis acid

(ii) the controlling agent

(iii) the monomers and the capping agent.

14. The method of claim 1 , wherein the amine-functionalized polyaryletherketone polymer is an amine-terminated polyaryletherketone polymer.

15. The method of claim 5 , wherein each Z is independently selected from the group consisting of —NHL, —NRL and —NL 2 , each L is a leaving group independently selected from the group consisting of an acetyl, haloacetyl, sulphonyl, halosulphonyl, —SO 2 —R, c is 1 to 10, each R is independently an aliphatic or aromatic group.

16. The method of claim 5 , wherein a is 1, 2 or 3.

17. The method of claim 5 , wherein b is 1, 2 or 3.

18. The method of claim 15 , wherein Z is —NHL, L is trifluoroacetyl, —SO 2 —CH 3 or —SO 2 —CF 3 , c is 1 to 4, a is 1, and b is 1.

19. The method of claim 7 , wherein Ar is an unsubstituted phenylene.

20. A method of preparing an amine-functionalized polyaryletherketone polymer, an imide- or sulphone-copolymer thereof or an amine-protected analogues thereof,

said method comprising:

polymerizing a monomer system in a reaction medium comprising a Lewis acid and a capping agent 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 group;

c is an integer;

Z is a protected amine group;

a is 1 to 5; and

b is 1 to 5.

21. The method of claim 20 , wherein said reaction medium further comprises a controlling agent.

Assignments (3)
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 23, 2018
From: TOWLE, IAN DAVID HENDERSON; SMITH, KAYLIE JANE
To: KETONEX LIMITED
Reel/Frame 046432/0508 →
Priority Claims (1)
GB 1409126.8 · May 22, 2014 · national
Continuity (1)
Related Publication 20170107323A1 · Apr 20, 2017
Cited By (1)
US 12,624,165