Polyarylene ether sulfone (PAES) compositions

Patent metadata

Field	Value
Publication number	US-9611361-B2
Application number	US-201414889648-A
Country	US
Kind code	B2
Filing date	Apr 30, 2014
Priority date	May 8, 2013
Publication date	Apr 4, 2017
Grant date	Apr 4, 2017

Abstract

A poly(arylether sulfone) polymeric material comprising polymer molecules wherein more than 50% moles of the recurring units of said polymer molecules are recurring units (Rt), equal to or different from each other, complying with formula (S t ): -E-Ar 1 —S0 2 -[Ar 2 -(T-Ar 3 ) n —S0 2 ] m -Ar 4 — (formula S t ) wherein: n and m, equal to or different from each other, are independently zero or an integer of 1 to 5, each of Ar 1 , Ar 2 , Ar 3 and Ar 4 equal to or different from each other and at each occurrence, is an aromatic moiety, T is a bond or a divalent group optionally comprising one or more than one heteroatom—E is of formula (E t ): wherein each of 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; j′ is zero or is an integer from 1 to 4; and wherein the fraction of polymer molecules having a molecular weight of below 5 000 [% fraction M <5000 , hereinafter] with respect to all the polymer molecules in said polymeric material is of at most 10% weight, and wherein said % fraction M <5000 is of at least [3.02-PDI] % when the polymeric material possesses a polydispersity index (PDI) of below 3.02.

First claim

The invention claimed is:

1. A poly(arylether sulfone) polymeric material, (t-PAES) polymeric material, comprising polymer molecules wherein more than 50% moles of the recurring units of said polymer molecules are recurring units (R t ), equal to or different from each other, complying with formula (S t ):
-E-Ar 1 —SO 2 —[Ar 2 -(T-Ar 3 ) n —SO 2 ] m —Ar 4 —  (formula S t )

wherein:
n and m, equal to or different from each other, are independently zero or an integer of 1 to 5;
each of Ar 1 , Ar 2 , Ar 3 and Ar 4 equal to or different from each other and at each occurrence, is an aromatic moiety;
T is a bond or a divalent group optionally comprising one or more than one heteroatom;
E is of formula (E t ):

wherein
each of 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;

j′ is zero or is an integer from 1 to 4; and
wherein the fraction of polymer molecules having a molecular weight of below 5,000, % fraction M <5000 , with respect to all the polymer molecules in said polymeric material is of at most 10% weight, and wherein said % fraction M <5000 is of at least [3.02-PDI] % when the polymeric material possesses a polydispersity index (PDI) of below 3.02.

2. The (t-PAES) polymeric material according to claim 1 , wherein said recurring units (R t ) are selected from the group consisting of those of formula (S t -1) to (S t -4) herein below:

wherein:
each of 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;
j′ is zero or is an integer from 1 to 4; and
T is a bond or a divalent group optionally comprising one or more than one heteroatom.

3. The (t-PAES) polymeric material according to claim 1 , wherein said polymer molecules additionally comprise recurring units (R a ) of formula (K a ):
-E-Ar 5 —CO—[Ar 6 -(T-Ar 7 ) n —CO] m —Ar 8 —  (formula K a )

wherein:
n and m, equal to or different from each other, are independently zero or an integer of 1 to 5;
each of Ar 5 , Ar 6 , Ar 7 and Ar 8 equal to or different from each other and at each occurrence, is an aromatic moiety;
T is a bond or a divalent group optionally comprising one or more than one heteroatom;
E is of formula (E t ):

wherein
each of 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.

4. The (t-PAES) polymeric material according to claim 1 , wherein said polymer molecules additionally comprise recurring units (R b ) comprising a Ar—SO 2 —Ar group, with Ar and Ar′, equal to or different from each other, are aromatic groups, said recurring units (R b ) complying with formula (S1):
—Ar 9 -(T′-Ar 10 ) n —O—Ar 11 —SO 2 —[Ar 12 -(T-Ar 13 ) n —SO 2 ] m —Ar 14 —O—  (S1):

wherein:
Ar 9 , Ar 10 , Ar 11 , Ar 12 , Ar 13 and Ar 14 , equal to or different from each other and at each occurrence, are independently an aromatic mono- or polynuclear group;
T and T′, equal to or different from each other and at each occurrence, is independently a bond or a divalent group optionally comprising one or more than one heteroatom; and
n and m, equal to or different from each other, are independently zero or an integer of 1 to 5.

5. The (t-PAES) polymeric material according to claim 1 , wherein said polymer molecules additionally comprise recurring units (R c ) comprising a Ar—C(O)—Ar′ group, with Ar and Ar′, equal to or different from each other, are aromatic groups, said recurring units (R c ) being selected from the group consisting of formulae (J-A) to (J-L):

wherein:
each of 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.

6. The (t-PAES) polymeric material according to claim 1 , wherein said (t-PAES) polymeric material has a polydispersity index (PDI) of more than 2.02.

7. A process for manufacturing the (t-PAES) polymeric material according to claim 1 , wherein the (t-PAES) polymeric material is a (t-PAES) polymer, comprising reacting in a solvent mixture comprising a polar aprotic solvent and in the presence of an alkali metal carbonate, a monomer mixture which comprises:
at least one dihydroxyaryl compound, diol (AA), of formula (T):

wherein:
each of 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;
j′ is zero or is an integer from 1 to 4;
at least one dihaloaryl compound, dihalo(BB), of formula (S):
X—Ar 1 —SO 2 —[Ar 2 -(T-Ar 3 ) n —SO 2 ] m —Ar 4 —X′  formula (S)

wherein
n and m, equal to or different from each other, are independently zero or an integer of 1 to 5; X and X′, equal to or different from each other, are halogens selected from F, Cl, Br, I;
each of Ar 1 , Ar 2 , Ar 3 and Ar 4 equal to or different from each other and at each occurrence, is an aromatic moiety;
T is a bond or a divalent group optionally comprising one or more than one heteroatom;
optionally, at least one dihydroxyaryl compound, diol (A′A′), different from diol (AA);
optionally, at least one dihaloaryl compound, dihalo (B′B′), different from dihalo (BB);

and at least 1% mole of at least one hydroxyl compound comprising only one reactive hydroxy group, agent (MOH), with respect to the total moles of diol (AA), and optionally of the diol (A′A′).

8. A process for manufacturing the (t-PAES) polymeric material according to claim 1 , comprising mixing:
i. from 0.1 to 15% wt. of at least one t-PAES (I-1) polymer having a number average molecular weight (M n ) below 18,000; and
ii. from 30 to 99.9% wt. of at least one t-PAES (I-2) polymer having a number average molecular weight (M n ) above 25,000;
wherein the % wt. is based on the total weight of t-PAES (I-1) polymer and t-PAES (I-2) polymer.

9. The process according to claim 8 , wherein the process comprises admixing the t-PAES (I-1) polymer and t-PAES (I-2) polymer by dry blending, solution mixing,

Assignees

• Solvay Specialty Polymers Usa

Inventors

• Louis Chantal
• El-Hibri Mohammad Jamal
• Thomas David B
• Patel Hemantkumar

Classifications

• C08G75/23 Primary

  Polyethersulfones · CPC title