Poly(ether ketone) polymers comprising cycloaliphatic units

Patent metadata

Field	Value
Publication number	US-9765176-B2
Application number	US-201314653645-A
Country	US
Kind code	B2
Filing date	Dec 19, 2013
Priority date	Dec 20, 2012
Publication date	Sep 19, 2017
Grant date	Sep 19, 2017

Abstract

A poly(ether ketone) polymer comprising recurring units derived from the reaction of at least one aromatic dihalo-compound comprising at least one —C(O)— group and at least one diol having a general formula HO-D ol -OH wherein D ol is an aliphatic group comprising from 4 to 20 carbon atoms which comprises at least one cycloaliphatic moiety.

First claim

The invention claimed is:

1. A poly(ether ketone) polymer comprising recurring units of formula (PEK-1):

wherein:
D ol is selected from the group consisting of formulae (Dol-1), (Dol-2), (Dol-3), (Dol-4) and (Dol-5):

Ar and Ar′ are aromatic moieties, independently selected from the group consisting of formulae (Ar-1), (Ar-2), (Ar-3), (Ar-4) and (Ar-5):

wherein each R, equal to or different from each other, is selected from the group consisting of halogen, alkyl, alkenyl, alkynyl, aryl, ether, thioether, carboxylic acid, ester, amide, imide, alkali or alkaline earth metal sulfonate, alkyl sulfonate, alkali or alkaline earth metal phosphonate, alkyl phosphonate, amine, and quaternary ammonium; and
j is zero or is an integer from 0 to 4.

2. The poly(ether ketone) polymer according to claim 1 , wherein the poly(ether ketone) polymer comprises recurring units selected from the group consisting of recurring units of formulae (i) to (vi), and mixtures thereof:

3. The poly(ether ketone) polymer according to claim 1 , wherein the poly(ether ketone) polymer comprises recurring units from a reaction of at least one diol of general formula (I):
HO-Dol-OH  (I)

wherein said diol is selected from the group consisting of diols of formulae (D-1) to (D-5):

and at least one aromatic dihalocompound of general formula (II):

wherein the Ar and Ar′ are aromatic moieties, independently selected from the group consisting of formulae (Ar-1), (Ar-2), (Ar-3), (Ar-4) and (Ar-5); and
X and X′, equal to or different from each other, are independently a halogen atom.

4. The poly(ether ketone) polymer according to claim 3 , wherein the at least one diol is 2,2,4,4-tetramethyl-1,3-cyclobutanediol of formula (D-1).

5. The poly(ether ketone) polymer according to claim 3 , wherein the at least one aromatic dihalocompound is 4,4′-difluorobenzophenone.

6. The poly(ether ketone) polymer according to claim 3 further comprising recurring units from an aromatic diol of formula (III):
HO-AD ol -OH  (III)

wherein AD ol is an aliphatic or aromatic group comprising from 4 to 30 carbon atoms, optionally comprising heteroatoms, which is different from D ol .

7. The poly(ether ketone) polymer according to claim 6 , wherein AD ol in formula (III) is selected from the group consisting of formulae (ADol-1) to (ADol-6):

8. The poly(ether ketone) polymer according to claim 3 , wherein the recurring units from the diol of formula (I) and the aromatic dihalocompound of formula (II) are at least 40 mol % of the total amount of recurring units.

9. A method of preparing the poly(ether ketone) polymer according to claim 3 which comprises reacting in a solvent mixture comprising a polar aprotic solvent: at least one alkali salt of the diol of formula (I); and at least one aromatic dihalocompound of the formula (II), wherein said alkali salt of the diol and said aromatic dihalocompound are reacted in a substantially equimolar amount.

10. A method of preparing the poly(ether ketone) polymer according claim 3 which comprises reacting in a solvent mixture comprising a polar aprotic solvent: the at least one diol of formula (I); and the at least one aromatic dihalocompound of formula (II); said diol and said aromatic dihalocompound being reacted in a substantially equimolar amount, in the presence of an alkali metal carbonate.

11. The method according to claim 9 additionally reacting in said solvent mixture at least one of: one diol of formula (III) or its alkali salt, which is different from the diol of formula (I),
HO-AD ol -OH  (III)

wherein AD ol is an aliphatic or aromatic group comprising from 4 to 30 carbon atoms, optionally comprising heteroatoms, which is different from D ol ; and/or
one dihalocompound of formula (IV), which is different from the aromatic dihalocompound of formula (II),

wherein A and A′ are aliphatic or aromatic groups, which are different from Ar and Ar′, having from 4 to 30 carbon atoms, optionally comprising heteroatoms; and
X and X′, equal to or different from each other, are independently a halogen atom.

12. The method according to claim 10 additionally reacting in said solvent mixture at least one of: one diol of formula (III) or its alkali salt, which is different from the diol of formula (I),
HO-AD ol -OH  (III)

wherein AD ol is an aliphatic or aromatic group comprising from 4 to 30 carbon atoms, optionally comprising heteroatoms, which is different from D ol ; and/or
one dihalocompound of formula (IV), which is different from the aromatic dihalocompound of formula (II),

wherein A and A′ are aliphatic or aromatic groups, which are different from Ar and Ar′, having from 4 to 30 carbon atoms, optionally comprising heteroatoms; and
X and X′, equal to or different from each other, are independently a halogen atom.

13. A composition comprising the poly(ether ketone) polymer of claim 1 .

14. An article comprising the poly(ether ketone) polymer of claim 1 .

Assignees

• Solvay Specialty Polymers Usa

Inventors

• Taylor Narmandakh
• Smith Deedee
• Roller David Blake

Classifications

• C08G10/00 Primary

  Condensation polymers of aldehydes or ketones with aromatic hydrocarbons or halogenated aromatic hydrocarbons only · CPC title

• C08G8/02

  of ketones · CPC title

• C08G65/34 Primary

  from hydroxy compounds or their metallic derivatives {(C08G65/26 takes precedence)} · CPC title

• C08G65/4012

  Other compound (II) containing a ketone group, e.g. X-Ar-C(=O)-Ar-X for polyetherketones · CPC title