# US 11,111,358 B2 · Stabilizer compounds

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- Number: US 11,111,358 B2
- Document ID: US11111358B2
- Status: Granted
- Kind: B2
- Application number: 16/710,469
- Filed: 2019-12-11
- Published: 2020-05-21
- Granted: 2021-09-07
- Earliest claimed: 2014-05-21
- Assignees: Solvay Specialty Polymers USA, LLC
- Applicants: Solvay Specialty Polymers USA, LLC
- Inventors: Joel Pollino; Gregory Goschy; Satchit Srinivasan
- Web page: https://patentgrep.com/patent/US11111358B2

## CPC

- C08K 5/3435: Piperidines
- C07D 211/46: having a hydrogen atom as the second substituent in position 4
- C08K 5/43: Compounds containing sulfur bound to nitrogen
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

A piperidine-based stabilizer compound of formula (I) or (II) that imparts UV, thermal, and/or thermo-oxidative stability to polymer compositions and more specifically to aromatic polymers and polymer compositions thereof.

## Claims

### Claim 1

Stabilizer compounds (SC) of formula (I) or formula (II):
wherein RJ is selected from the group consisting of —H, —CH3, —CH2CH3, —OCH3, and —OCH2CH3, and
wherein each of RK, equal or different from each other and from RJ, is selected from the group consisting of:
wherein RL is a monovalent substituent of general formula (Y-I):
wherein Ri and Rm are the same or different from each other and are independently selected from the group consisting of H,
and alkyl groups of formula —CH3, —CH2OCH3 and
and
wherein Ri is either in an ortho, meta or para position, and
wherein Rm is either in an ortho or meta position, and
wherein Q is —SO2—, and
wherein RN is a divalent substituent selected from the group consisting of general formula (Z-I):
wherein Ri and Rm are the same or different from each other and are independently selected from the group consisting of —H,
alkyl groups of formula —CH3, —CH2OCH3 and
wherein Ri and Rm are independently either in an ortho or meta position, and
wherein Q is —SO2—.

### Claim 2 (depends on 1)

The stabilizer compounds (SC) of formula (I) of claim 1, wherein said stabilizer compound (SC) is:

### Claim 3 (depends on 1)

The stabilizer compounds (SC) of formula (H) of claim 1, wherein said stabilizer compound (SC) is:

### Claim 4 (depends on 1)

The stabilizer compound (SC) according to claim 1, wherein Rm is —H.

### Claim 5 (depends on 1)

A method for the manufacture of the stabilizer compound of formula (I) of claim 1, comprising the step of reacting compounds of formulae (III) and (IV) together in the presence of a base;
wherein Xi is a halogen selected from the group consisting of chlorine, fluorine, bromine, and iodine, and
wherein RJ, RK, RL are as defined in claim 1 for formula (I).

### Claim 6 (depends on 1)

A method for the manufacture of the stabilizer compound of formula (II) of claim 1, comprising the step of reacting compounds of formulae (111) and (IV) together in the presence of a base:
wherein Xi or Xj are the same or independently selected halogens from the group consisting of chlorine, fluorine, bromine, and iodine, and
wherein RJ, RK, RN are as defined in claim 1 for formula (II).

### Claim 7 (depends on 6)

The method of claim 6, wherein the reaction is carried out in a polar aprotic solvent.

### Claim 8 (depends on 7)

The method of claim 7, wherein the polar aprotic solvent is tetrahydrofuran and the reaction is carried out at a temperature of between 25° C. and 66° C.

### Claim 9 (depends on 7)

The method of claim 7, wherein the polar aprotic solvent is N-methylpyrrolidone and the reaction is carried out at a temperature of between 25° C. and 204° C.

### Claim 10 (depends on 1)

A polymer composition (P), comprising at least one stabilizer compound (SC) of claim 1 and at least one polymer 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 (P) of claim 10, wherein the at least one polymer is selected from the group consisting of polyketones, poly(etherketone)s, and poly(ethersulfone)s.

### Claim 12 (depends on 10)

The polymer composition (P) of 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 13 (depends on 1)

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

### Claim 14 (depends on 13)

The method of claim 13, where the at least one stabilizing compound (SC) acts as an acid scavenger for the at least one polymer.

### Claim 15 (depends on 10)

An article comprising the polymer composition (P) of claim 10.