# US 11,111,215 B2 · Piperidine-based stabilizers and polymers end-capped with the same

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- Number: US 11,111,215 B2
- Document ID: US11111215B2
- Status: Granted
- Kind: B2
- Application number: 16/711,050
- Filed: 2019-12-11
- Published: 2020-04-16
- Granted: 2021-09-07
- Earliest claimed: 2014-05-21
- Assignees: Solvay Specialty Polymers USA, LLC
- Applicants: Solvay Specialty Polymers USA, LLC
- Inventors: Joel Pollino; Satchit Srinivasan; Henry Bradley; Claire Hartmann-Thompson; Gregory Goschy
- Web page: https://patentgrep.com/patent/US11111215B2

## CPC

- C07D 211/46: having a hydrogen atom as the second substituent in position 4
- C08G 75/23: Polyethersulfones
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS

## Abstract

The invention relates to piperidine-based compounds of formula (I) that are used to improve UV, thermal, and thermo-oxidative stability of high performance aromatic polymers in a blend or as end-cappers of the same polymers.

## Claims

### Claim 1

An end-capper stabilizer compound (EC) of the general structural formula (I):
wherein:
Rk is selected from the group consisting of —H, aliphatic groups, and alkoxy groups, and
Rj groups are equal to or different from each other and from Rk and are independently selected from aliphatic groups, and
Y is a monovalent group selected from a first group consisting of a halogen, a carboxylic ester, an acid halide, an anhydride, an amide, and a thioester or from a second group consisting of a hydroxyl, an amine, a carboxylic acid, a thiol, and any protected derivative thereof, and
A is a divalent group of formula:

### Claim 2 (depends on 1)

A method for the manufacture of the end-capper stabilizer compound (EC) according to claim 1, comprising the step of reacting compounds of formulae (III) and (IV) together in the presence of a base;
wherein:
Rk is selected from the group consisting of —H, aliphatic groups, and alkoxy groups, and
Rj groups are equal to or different from each other and from Rk and are independently selected from aliphatic groups, and
Z is a halogen, and
Y is a monovalent group selected from a first group consisting of a halogen, a carboxylic ester, an acid halide, an anhydride, an amide, and a thioester or from a second group consisting of a hydroxyl, an amine, a carboxylic acid, a thiol, and any protected derivative thereof, and
A is a divalent group of formula:

### Claim 3 (depends on 2)

The method of claim 2, wherein the reaction is carried out in a polar aprotic solvent.

### Claim 4

An end capped polymer (EP) comprising recurring units and at least two chain ends, wherein at least one of the chain ends comprises the general structural formula (V):
wherein:
Rk is selected from the group consisting of —H, aliphatic groups, and alkoxy groups, and
Rj groups are equal to or different from each other and from Rk and are independently selected from aliphatic groups, and
X is a divalent group selected from the group consisting of —O—, —(C═O)—NH—, —(C═O)—, —(C═O)—O—, —(C═O)—S—, —NH— and —S—, and
A is a divalent group of formula:

### Claim 5 (depends on 4)

A method for the manufacture of the end capped polymer (EP) according to claim 4 comprising the step of reacting the end-capper stabilizer compound (EC) with at least:
a polymer comprising at least one reactive chain end, or
a monomer comprising at least one reactive group
wherein the at least one reactive chain end or the at least one reactive group is able to react with the monovalent group Y of the general structural formula (I).

### Claim 6 (depends on 5)

The method according to claim 5, wherein the at least one reactive chain end or the at least one reactive group is selected from a first group consisting of a halogen, a carboxylic ester, an acid halide, an anhydride, an amide, and a thioester or from a second group consisting of a hydroxyl, an amine, a carboxylic acid, a thiol, and any protected derivative thereof.

### Claim 7 (depends on 5)

The method according to claim 5, wherein the at least one reactive chain end or the at least one reactive group is a halogen and the monovalent group Y of the end-capper stabilizer compound (EC) is a hydroxyl.

### Claim 8 (depends on 1)

A polymer composition (C) comprising at least one end-capper stabilizer compound (EC) according to claim 1.

### Claim 9 (depends on 4)

A polymer composition (C) comprising at least one end capped polymer (EP) of claim 4 and at least one polymer (P*).

### Claim 10 (depends on 9)

The polymer composition (C) according to claim 9, wherein the polymer (P*) is selected from the group consisting of polyolefins, polyesters, polyethers, polyketones, poly(etherketone)s, poly(ethersulfone)s, polyamides, polyurethanes, polystyrenes, polyacrylates, polymethacrylates, polyacetals, polytetrafluoroethylene, polyvinylidene fluoride, polyacrylonitriles, polybutadienes, acrylonitrile butadiene styrene, styrene acrylonitrile, acrylate styrene acrylonitrile, cellulosic acetate butyrate, cellulosic polymers, polyimides, polyamideimides, polyetherimides, polyphenylsulfides, polyphenylene oxides, polyvinylchlorides, polyvinylbutyrates, polycarbonates, epoxy resins, polysiloxanes, and polyketimines.

### Claim 11 (depends on 10)

The polymer composition (C) according to claim 10, wherein it further comprises at least another ingredient selected from the group consisting of dyes, pigments, fillers, UV stabilizers, light stabilizers, optical brighteners.

### Claim 12 (depends on 1)

A method for stabilizing a polymer comprising adding at least one stabilizing compound (EC) according to claim 1.

### Claim 13 (depends on 4)

A method for stabilizing a polymer comprising adding at least one end capped polymer (EP) according to claim 4 to at least one polymer (P*).

### Claim 14 (depends on 12)

The method of claim 12, where the at least one stabilizing compound (SC) acts as an acid scavenger for the at least one polymer (P*).

### Claim 15 (depends on 13)

The method of claim 13, where the at least one end capped polymer (EP) acts as an acid scavenger for the at least one polymer (P*).

### Claim 16 (depends on 9)

An article comprising the polymer composition (C) according to claim 9.