Method for decreasing the concentration of a metal in a monomer composition comprising bis(benzoyl)benzene

Patent metadata

Field	Value
Publication number	US-11420920-B2
Application number	US-201716471522-A
Country	US
Kind code	B2
Filing date	Dec 19, 2017
Priority date	Dec 21, 2016
Publication date	Aug 23, 2022
Grant date	Aug 23, 2022

Abstract

Disclosed are methods of decreasing the concentration of a metal in a monomer composition including a bis(benzoyl)benzene, bis(benzoyl)benzene monomer compositions having a low total metal concentration, di-ketone polymers made from low metal bis(benzoyl)benzene monomers, and polymer compositions and shaped articles including the di-ketone polymers. It was surprisingly found that di-ketone polymers made by nucleophilic substitution of low metal bis(benzoyl)benzene monomers exhibit greater crystallinity, as compared with di-ketone polymers made with conventional monomers.

First claim

The invention claimed is:

1. A method for decreasing the concentration of a metal in a monomer composition comprising:
b) recrystallizing the monomer composition in a first solvent (Solvent A), wherein:
the first solvent (Solvent A) includes at least 10 wt. % of an aprotic solvent having a dielectric constant greater than 30, relative to the total weight of the first solvent (Solvent A), and
the first solvent (Solvent A) includes less than 1 wt. % of inorganic salts relative to the total weight of the first solvent (Solvent A), and
the monomer composition comprises a compound of formula:

wherein:
R 1 , R 2 , R 3 and R 4 , at each instance, is independently selected from the group consisting of an alkyl, an alkenyl, an alkynyl, an aryl, an ether, a thioether, a carboxylic acid, an ester, an amide, an imide, an alkyl sultanate, an alkyl phosphonate, an amine, and a quaternary ammonium;
i, j, k and L, at each instance, is an independently selected integer ranging from 0 to 4;
X is a halogen; and
further wherein the decreasing the concentration of a metal in a monomer composition forms a low metal monomer.

2. The method of claim 1 , further comprising:
a) dissolving the monomer composition prior to the recrystallizing, wherein dissolving the monomer composition includes heating the monomer composition in the first solvent (Solvent A) to a first temperature (T 1 ) to form a monomer solution;
wherein:
the concentration of the monomer composition in the first solvent (Solvent A) ranges from about 10 to about 20 wt. % relative to the combined weight of the monomer composition and the first solvent (Solvent A); and
the first temperature (T 1 ) ranges from about 50 to about 240° C.

3. The method of claim 1 , wherein recrystallizing the monomer composition comprises:
b1) optionally passing the monomer solution through a first filter;
b2) optionally distilling off a portion of the first solvent (Solvent A) at a second temperature (T 2 ),
b3) optionally adding a second solvent (Solvent B) to the monomer solution when the first solvent (Solvent A) is at a third temperature (T 3 ) to form a solvent mixture,
wherein the solubility of the monomer composition in the solvent mixture is less than the solubility of the monomer composition in the first solvent (Solvent A); and
b4) optionally cooling the monomer solution to a fourth temperature (T 4 ) ranging from about −10 to about 40° C., provided that the fourth temperature (T 4 ) is greater than the melting point of the first solvent (Solvent A) and the optional second solvent (Solvent B);
provided that the method includes at least one of steps b2) and b4), and that step b1), when present, is performed before steps b2), b3), and b4), when present,
wherein the first temperature (T 1 ), the second temperature (T 2 ), and the third temperature (T 3 ), identical to or different from each other, are independently selected from temperatures ranging from about 50 to about 240° C.

4. The method of claim 3 , wherein the second solvent (Solvent B) is added to the monomer solution at a concentration ranging from about 5.0 to about 50 wt. % relative to the total weight of the first (solvent A) and second solvent (Solvent B).

5. The method of claim 1 , further comprising:
c) recovering the monomer composition after the recrystallizing, wherein recovering the monomer composition comprises:
c1) removing the monomer composition from the monomer solution by passing the monomer solution through a second filter;
c2) optionally washing the monomer composition with a third solvent (Solvent C), wherein the third solvent (Solvent C) is identical to the first solvent (Solvent A), the second solvent (Solvent B), or a combination thereof; and
c3) drying the monomer composition.

6. The method of claim 1 , wherein the inorganic salts comprise halides or oxides of Group IA, IIA, IIIa or VIII metals, or combinations thereof.

7. The method of claim 1 , wherein the first solvent (Solvent A) comprises dimethyl sulfoxide (DMSO), sulfolane, propylene carbonate, N,N′-dimethylformamide (DMF), N,N′-dimethylacetamide (DMAc), N-methylpyrrolidinone (NMP), 1,3-dimethyl-2-oxo-hexahydropyrimidine (DMPU), 1,3-dimethylimidazolidin-2-one (DMEU), or combinations thereof.

8. The method of claim 3 , wherein the second solvent (Solvent B) comprises water, ethanol, methanol, isopropanol, acetone, acetic acid, acetonitrile, ethyl acetate, diethyl ether, tetrahydrofuran, dipropyl ether, or combinations thereof.

9. The method of claim 1 , wherein the method yields 90 wt. % or greater of the monomer composition, relative to the weight of the monomer composition before the recrystallizing.

10. The method of claim 1 , wherein the low metal monomer has a total metal concentration less than 30 wt.ppm, relative to the total weight of the monomer composition.

11. A di-ketone polymer synthesized by nucleophilic substitution from monomers including bis(benzoyl)benzene monomers, wherein at least 80 mol % of the bis(benzoyl)benzene monomers are bis(benzoyl)benzene monomers recrystallized according to the method of claim 1 .

12. A di-ketone polymer synthesized by nucleophilic substitution of monomers including bis(benzoyl)benzene monomers, wherein at least 80 mol % of the bis(benzoyl)benzene monomers are low metal monomers.

13. The di-ketone polymer of claim 11 , wherein the metal comprises at least aluminum and/or iron, and wherein the sum of the concentrations of aluminum and iron in the di-ketone polymer is less than 30 wt.ppm, relative to the weight of the di-ketone polymer.

14. The di-ketone polymer of claim 12 , wherein the metal comprises at least aluminum and/or iron, and wherein the sum of the concentrations of aluminum and iron in the di-ketone polymer is less than 30 wt.ppm, relative to the weight of the di-ketone polymer.

15. A shaped article comprising the di-ketone polymer of claim 11 , wherein the shaped article is a component of an mobile electronic device or a medical device.

16. A shaped article comprising the di-ketone polymer of claim 12 , wherein the shaped article is a component of an mobile electronic device or a medical device.

17. The method of claim 1 , wherein X is fluorine or chlorine.

Assignees

• Solvay Specialty Polymers Usa

Inventors

• Louis Chantal
• Harding Scott A

Classifications

• C08G65/40

  from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group · CPC title

• C07C2601/16

  the ring being unsaturated · CPC title

• C07C49/303

  to a six-membered ring · CPC title

• C07C45/81 Primary

  by change in the physical state, e.g. crystallisation · CPC title

• C08G65/38

  derived from phenols · CPC title