Polymer additive and a method for the production thereof

Patent metadata

Field	Value
Publication number	US-10745353-B2
Application number	US-201615739458-A
Country	US
Kind code	B2
Filing date	May 31, 2016
Priority date	Jul 3, 2015
Publication date	Aug 18, 2020
Grant date	Aug 18, 2020

Abstract

The invention relates to a compound of formula (I), characterised by the characteristic signals in the X-ray diffraction powder pattern measured with Cu Kalpha radiation (0.154 nm) at a 2-theta angle of 15.0 and 22.7 with a high intensity, and of 5.0, 11.3, 18.9, 20.8, 21.6 and 23.6 with a medium intensity, as well as to a method for producing the compound of formula (I) by reacting at least one isophthalic acid diester of formula (II) where R1 and R2 are the same or different and stand for an aliphatic group, with two equivalents 4-amino-2,2,6,6-tetramethylpiperidine, in the presence of at least one catalyst from the group of metal alcoholates and at a reaction temperature of between 50 and 150° C.

First claim

The invention claimed is:

1. A compound of the formula (I)

wherein an X-ray powder diffraction pattern of the compound has characteristic signals measured with Cu K alpha radiation at a 2-theta angle of 15.0 and 22.7 having a high intensity and of 5.0, 11.3, 18.9, 20.8, 21.6 and 23.6 having a moderate intensity.

2. A process for preparing the compound of the formula (I) as claimed in claim 1 , comprising reacting at least one isophthalic diester of the formula (II)

wherein R 1 and R 2 are the same or different and are an aliphatic radical, with 2 equivalents of 4-amino-2,2,6,6-tetramethylpiperidine in the presence of at least one catalyst, wherein the at least one catalyst is a metal alkoxide, at a reaction temperature between 50 and 150° C.

3. The process as claimed in claim 2 , wherein the metal alkoxide is a compound of the formula (VI) and/or (VII)
X—OR 13   (VI)

R 14 O—Y—OR 15   (VII)

wherein
R 14 and R 15 are each the same or different;
R 13 , R 14 and R 15 are aliphatic radicals each having 1 to 20 carbon atoms;
X is an alkali metal; and
Y is an alkaline earth metal.

4. The process as claimed in claim 2 , wherein the metal alkoxide is sodium methoxide, potassium methoxide, lithium methoxide, sodium ethoxide, potassium ethoxide, lithium ethoxide, sodium n-propoxide, potassium n-propoxide, sodium isopropoxide, potassium isopropoxide, sodium butoxide, potassium butoxide, sodium isobutoxide, potassium isobutoxide, sodium sec-butoxide, potassium sec-butoxide, sodium tert-amoxide, sodium amoxide, potassium amoxide, potassium tert-butoxide or a combination thereof.

5. The process as claimed in claim 2 , wherein the metal alkoxide is added to the reaction mixture in amounts of 1 to 20 mol %, based on the isophthalic diester.

6. The process as claimed in claim 2 , wherein the reaction is conducted solvent-free and in a reaction apparatus selected from the group consisting of mixers, kneaders and extruders.

7. The process as claimed in claim 6 , wherein the reaction mixture, after the addition of the at least one catalyst, is mixed by the kneader, mixer or extruder at the reaction temperature for a period of 10 to 400 minutes.

8. The process as claimed in claim 6 , wherein the kneader or mixer is equipped with sigma blades, masticator blades, plowshares, Becker blades, throwing paddles or a combination thereof.

9. The process as claimed in claim 2 , wherein the isophthalic diester is dissolved in an excess of the 4-amino-2,2,6,6-tetramethylpiperidine.

10. The process as claimed in claim 2 , wherein the isophthalic diester is dissolved together with two equivalents of the 4-amino-2,2,6,6-tetramethylpiperidine and a lipophilic liquid hydrocarbon or a mixture thereof.

11. The process as claimed in claim 2 , wherein alcohol formed in the reaction is removed from the reaction mixture.

12. The process as claimed in claim 2 , wherein the compound of the formula (I) precipitates out of the reaction mixture in solid form.

13. A polymer additive comprising a compound of the formula (I) as claimed in claim 1 .

14. A stabilized polymer comprising a compound of the formula (I) as claimed in claim 1 , wherein the stabilized polymer is stabilized against light and heat and has oxygen barrier properties.

15. The polymer additive as claimed in claim 13 , wherein the polymer is selected from the group consisting of polyamides, polyesters and EVOH.

Assignees

• Clariant Plastics & Coatings Ltd

Inventors

• Sahl Mike
• Zeisberger Eduard
• Zaeh Matthias
• Schacker Ottmar
• Steffanut Pascal

Classifications

• C08L23/0846

  with unsaturated hydrocarbons containing atoms other than carbon or hydrogen · CPC title

• C08L2201/14

  Gas barrier composition · CPC title

• C07D211/58 Primary

  attached in position 4 · CPC title

• C08K5/3435

  Piperidines · CPC title

• C08L77/00

  Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain (of polyhydrazides C08L79/06; of polyamideimides or polyamide acids C08L79/08); Compositions of derivatives of such polymers · CPC title