CS253935B1 - Copolyesters based on poly (ethylene-2-butenedionate) modified by polyanalogeneic reaction with 4-amino-2,2,6,6-tetramethylpiperidine and their preparation - Google Patents

Copolyesters based on poly (ethylene-2-butenedionate) modified by polyanalogeneic reaction with 4-amino-2,2,6,6-tetramethylpiperidine and their preparation Download PDF

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CS253935B1
CS253935B1 CS951385A CS951385A CS253935B1 CS 253935 B1 CS253935 B1 CS 253935B1 CS 951385 A CS951385 A CS 951385A CS 951385 A CS951385 A CS 951385A CS 253935 B1 CS253935 B1 CS 253935B1
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formula
butenedionate
tetramethylpiperidine
ethylene
amino
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CS951385A
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Czech (cs)
Slovak (sk)
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Frantisek Vass
Zdenek Manasek
Jozef Luston
Gabriela Vassova
Andrej Romanov
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Frantisek Vass
Zdenek Manasek
Jozef Luston
Gabriela Vassova
Andrej Romanov
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Priority to CS951385A priority Critical patent/CS253935B1/en
Publication of CS253935B1 publication Critical patent/CS253935B1/en

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Abstract

Riešenie sa týká kopolyesterov na báze poly(etylén-2-buténdionátu) modifikovaných polyméranalogickou reakciou so 4-amíno- -2,2,6,6-tetrametylpiperidínom vzorca I, kde m + n nadobúdajú hodnoty 2 až 100 a spůsotou ich přípravy. Podstata postupu přípravy týchto kopolymérov spočívá v tom, že sa na poly(etylén-2-buténdionát) vzorca II, kde x je 2 až 100, působí 4-amíno-2,2,6,6-tetrametylpiperidínom vzorca III, pričom mólový poměr zlúčeniny vzorca II ku zlúčenine vzorca III je 1:1 až 1: 0,2, najvýhodnejšie v chloroforme za miešania po dobu 4 až 10 hodin pri teplote spatného toku. Riešenie má použitie pre svetelnú stabilizáciu polymérov, osobitne polyolefínov.The solution relates to copolyesters based on poly(ethylene-2-butenedionate) modified by polymer-analogous reaction with 4-amino-2,2,6,6-tetramethylpiperidine of formula I, where m + n take the values 2 to 100, and to a method for their preparation. The essence of the method for preparing these copolymers consists in that poly(ethylene-2-butenedionate) of formula II, where x is 2 to 100, is treated with 4-amino-2,2,6,6-tetramethylpiperidine of formula III, wherein the molar ratio of the compound of formula II to the compound of formula III is 1:1 to 1:0.2, most preferably in chloroform with stirring for 4 to 10 hours at reflux temperature. The solution is used for light stabilization of polymers, especially polyolefins.

Description

Riešenie sa týká kopolyesterov na báze poly(etylén-2-buténdionátu) modifikovaných polyméranalogickou reakciou so 4-amíno-2,2,6,6-tetrametylpiperidínom vzorca I, kde m + n nadobúdajú hodnoty 2 až 100 a spůsotou ich přípravy. Podstata postupu přípravy týchto kopolymérov spočívá v tom, že sa na poly(etylén-2-buténdionát) vzorca II, kde x je 2 až 100, působí 4-amíno-2,2,6,6-tetrametylpiperidínom vzorca III, pričom mólový poměr zlúčeniny vzorca II ku zlúčenine vzorca III je 1:1 až 1: 0,2, najvýhodnejšie v chloroforme za miešania po dobu 4 až 10 hodin pri teplote spatného toku.The solution relates to copolyesters based on poly(ethylene-2-butenedionate) modified by polymer-analogous reaction with 4-amino-2,2,6,6-tetramethylpiperidine of formula I, where m + n take the values 2 to 100, and to a method for their preparation. The essence of the method for preparing these copolymers consists in treating poly(ethylene-2-butenedionate) of formula II, where x is 2 to 100, with 4-amino-2,2,6,6-tetramethylpiperidine of formula III, where the molar ratio of compound of formula II to compound of formula III is 1:1 to 1:0.2, most preferably in chloroform with stirring for 4 to 10 hours at reflux temperature.

Riešenie má použitie pre svetelnú stabilizáciu polymérov, osobitne polyolefínov.The solution has applications for light stabilization of polymers, especially polyolefins.

Vynález sa, týká: kopolyesterov na báze poly[etylén-2-buténdionátu) modifikovaných polyméranologickou reakciou só 4-amíno-2,2,6,6-tetrametylpiperidínom a spůsobu ich přípravy. ’The invention relates to: copolyesters based on poly[ethylene-2-butenedionate) modified by polymerisation reaction with 4-amino-2,2,6,6-tetramethylpiperidine and a method for their preparation.

Stéricky bráněné i aminy posobenia ako vysokoúčinné svetelhé stabilizátory polytnérov. Inhibujú nežiadúce radikálové procesy, ktoré prebiehajú v podmienkách prírodného stárnutia polyrpérov. Nevýhodou nízkomolekulových stériicky bráněných derivátov piperidínu je ich značná prchavosť a extrahovatelnosť z užitkového polyméru. Pri teplotnom spracovaní dochádza v důsledku prchavosti k zníženiu koncentrácie nízkomolekulových stabilizátorov z polymerných systémov.Steric hindered amines act as highly effective light stabilizers of polymers. They inhibit undesirable radical processes that occur under conditions of natural aging of polymers. The disadvantage of low-molecular-weight sterically hindered piperidine derivatives is their considerable volatility and extractability from the useful polymer. During thermal processing, the concentration of low-molecular-weight stabilizers from polymer systems decreases due to volatility.

Uvedené nevýhody tento vynález odstraňuje. Podstatou vynálezu je kopolyester na báze poly(etylén-2-buténdionátuj modifikovaný polyméranalogickou reakciou so 4-amíno-2,2,6,6-tetrametylpiperidínom vzorca IThe present invention eliminates the above disadvantages. The essence of the invention is a copolyester based on poly(ethylene-2-butenedionate) modified by polymer analog reaction with 4-amino-2,2,6,6-tetramethylpiperidine of formula I

í í jZ-· jZ-· 0 II 0 II 0 CH - CH^C-OCH^CH^O- 0 CH - CH^C-OCH^CH^O- o (ó - c- CH^CH-C-O-CHžCHgO- o ( ó - c- CH^CH-CO-CHžCHgO- L L NH 1 NH 1 h3c r h 3 cr ^n^ch3 ^n^ch 3 H H L- L- m m

kde m + n nadobúdajú hodnoty 2 až 100. Podstatou vynálezu je ďalej spůsob přípravy zlúčeniny vzorca I, vyznačujúci sa tým, že sa na poly(etylén-2-buténdionát) vzorca IIwhere m + n take the values 2 to 100. The invention further provides a method for preparing a compound of formula I, characterized in that poly(ethylene-2-butenedionate) of formula II

O oAbout

C-CW=CH-C-O-CHj-CH^OC-CW=CH-C-O-CHj-CH^O

() kde x je 2 až 100, působí 4-amíno-2,2,6,6-tetrametylpiperidínom vzorce III() where x is 2 to 100, acts with 4-amino-2,2,6,6-tetramethylpiperidine of formula III

(0 v mólovom pomere zlúčeniny vzorca II ku zlúčenine vzorca III 1:1 až 1: 0,2, výhodné v chloroforme za miešania po dobu 4 až 10 hodin pri teplote spatného toku.(0) in a molar ratio of compound of formula II to compound of formula III of 1:1 to 1:0.2, preferably in chloroform with stirring for 4 to 10 hours at reflux temperature.

Polymérne světelné stabilizátory piperidínového typu, ktoré sú predmetom vynálezu sú vhodné pre stabilizáciu polymérov, najma polyolefínov.The polymeric light stabilizers of the piperidine type, which are the subject of the invention, are suitable for stabilizing polymers, especially polyolefins.

Příklad 1Example 1

K roztoku 1,41 g poly(etylén-2-buténdionátuj II (koncentrácia štruktúrnych článkov kyseliny 2-buténdiovej 0,01 mólu, Mn = = 3 200) v 25 ml chloroformu sa přidá 1,578 gramov (0,0101 mólu) 4-amíno-2,2,6,6-tetrametylpiperidínu III a reakčná zmes sa mieša pri teplote spatného toku po dobu 7 hodin. Po ochladení sa rozpúšťadlo odpaří vo vákuovej rotačnej odparke a k mazlavému zvyšku sa přidá 30 ml díetylénéteru. Po hodinovém státí a občasnom pretrepaní zmesi sa vylúčený stuhnutý zvyšok viacnásobne extrahuje dietyléterom. Po odpaření dietyléteru sa získá tuhý, žltkastý, 1'ahko spráškovatelný polymér vo výtažku 93 % s teplotou topenia 57 až 62 °C s obsahom dusíka 8,9 % a Mn = 2 190 (stanovené metódou VPO).To a solution of 1.41 g of poly(ethylene-2-butenedionate) II (concentration of 2-butenedioic acid structural units 0.01 mol, M n = = 3,200) in 25 ml of chloroform is added 1.578 grams (0.0101 mol) of 4-amino-2,2,6,6-tetramethylpiperidine III and the reaction mixture is stirred at reflux temperature for 7 hours. After cooling, the solvent is evaporated in a vacuum rotary evaporator and 30 ml of diethylene ether is added to the oily residue. After standing for an hour and occasional shaking of the mixture, the precipitated solidified residue is extracted several times with diethyl ether. After evaporation of the diethyl ether, a solid, yellowish, easily pulverizable polymer is obtained in a yield of 93% with a melting point of 57 to 62 °C and a nitrogen content of 8.9% and M n = 2,190 (determined by the VPO method).

IČ spektrum (chloroform) bul'ke uvedené ďalšie výsledky syntéz kopolyesterov vzorca I polyméranalogickými re»max — 3 320, 2 980, 2 870, 1730, 1610, 1390, akciami poly(etylén-2-buténdionátu II so 41 380, 1180 cm-1. -amíno-2,2,6,6-tetrametylpiperidínom III v příslušných molových pomeroch.IR spectrum (chloroform) presented in the table further results of the synthesis of copolyesters of formula I with polymer analogs re»max — 3 320, 2 980, 2 870, 1730, 1610, 1390, by the actions of poly(ethylene-2-butenedionate II with 41 380, 1180 cm -1 . -amino-2,2,6,6-tetramethylpiperidine III in the appropriate molar ratios.

Příklad 2 až 5Example 2 to 5

V príkladoch 2 až 5 sú v nasledujúcej taPríklad Molový poměr Teplota topenia Výťažok Mn 10-3 Doba % NIn Examples 2 to 5, the following table shows the molar ratio of the following compounds: Example Molar ratio Melting point Yield M n 10 -3 Time % N

č. II: III °C % reakcie hNo. II: III °C % reaction h

2 2 1:0,8 1:0.8 59 až 65 59 to 65 87,68 2,68 87.68 2.68 7 7 7,94 7.94 3 3 1: 0,6 1: 0.6 61 až 70 61 to 70 94,95 2,72 94.95 2.72 5 5 6,51 6.51 4 4 1 : 0,4 1 : 0.4 63 až 74 63 to 74 97,23 3,35 97.23 3.35 10 10 4,89 4.89 5 5 1:0,2 1:0.2 70 až 78 70 to 78 91,99 3,26 91.99 3.26 7 7 2,74 2.74 Vynález Invention má použitie has a use pre svetelnú stabilizáciu polymérov, osobitne polyolefínov. for light stabilization of polymers, especially polyolefins.

PREDMETSUBJECT

Claims (2)

5 253935 IČ spektrum (chloroform) bul'ke uvedené dalšie výsledky syntéz kopo- lyesterov vzorca I polyméranalogickými re- »max — 3 320, 2 980, 2 870, 1730, 1610, 1390, akciami poly(etylén-2-buténdionátu II so 4-1 380, 1180 cm-1. -amíno-2,2,6,6-tetrametylpiperidínom III v příslušných molových pomeroch. Příklad 2 až 5 V príkladoch 2 až 5 sú v nasledujúcej ta- Príklad Molový poměr Teplota topenia Výťažok Mn 10-3 Doba % N č. II: III °C % reakcie h 2 1:0,8 59 až 65 87,68 2,68 7 7,94 3 1: 0,6 61 až 70 94,95 2,72 5 6,51 4 1 : 0,4 63 až 74 97,23 3,35 10 4,89 5 1:0,2 70 až 78 91,99 3,26 7 2,74 Vynález má použitie pre svetelnú stabilizáciu polymérov, osobitne polyolefínov. PREDMET VYNALEZU5 253935 IR spectrum (chloroform) The other results of the synthesis of copolymers of the formula I by polymeric analogs - 3202, 2980, 2870, 1730, 1610, 1390, by the actions of poly (ethylene-2-butenedionate II) EXAMPLES 2 to 5 In Examples 2 to 5, the following is an example: mole ratio Melting point Yield: Mn 10 4 - 380, 1180 cm -1, -amino-2,2,6,6-tetramethylpiperidine III in appropriate molar ratios. -3 Time% N No II: III ° C% Reaction h 2 1: 0.8 59 to 65 87.68 2.68 7 7.94 3 1: 0.6 61 to 70 94.95 2.72 5 6.51 4 1: 0.4 63 to 74 97.23 3.35 10 4.89 5 1: 0.2 70 to 78 91.99 3.26 7 2.74 The invention has application for the light stabilization of polymers, in particular polyolefins 1. Kopolyestery na báze poly(etylén-2-bu-téndionátu) modifikovaného polyméranalo- gickou reaikciou so 4-amino-2,2,6,6-tetrame-tylpiperidínom vzorca I1. Copolyesters based on poly (ethylene-2-butenedionate) modified by polymeric reaction with 4-amino-2,2,6,6-tetramethylpiperidine of the formula I o o • c- CH-CH-C-Q-CH^CH^O ftl řl kde m + n nadobúdajú hodnoty 2 až 100.o-c-CH-CH-C-Q-CH 2 CH 2 O-f-1 where m + n is 2 to 100. 2. Sposob přípravy kopolyesteru vzorca I podlá bodu 1, vyznačujúci sa tým, že sa napóly(etylén-2-buténdionát)vzorca II O ó li i< C“ C H-CH- C- O “ C HjrCHgO2. A process for the preparation of a copolyester of the formula I according to claim 1, characterized in that the (ethylene-2-butenedionate) of the formula (II) is (O) 1 (C) C H-CH-C (O) C HjrCHgO. (II) kde x je 2 až 100, pósobí so 4-amíno-2,2,6,6--tetrametylpiperidínom vzorca III v molovom pomere zlúčeniny vzorce II ku zlúčenine vzorca III 1:1 až 1:0,2, najvý- hodnejšie v chloroforme za miešania po do- bu 4 až 10 hodin pri teplote spatného' toku.(II) wherein x is 2 to 100, with 4-amino-2,2,6,6-tetramethylpiperidine of the formula III in a molar ratio of the compound of the formula II to the compound of the formula III 1: 1 to 1: 0.2; more preferably in chloroform with stirring for 4 to 10 hours at a reflux temperature.
CS951385A 1985-12-19 1985-12-19 Copolyesters based on poly (ethylene-2-butenedionate) modified by polyanalogeneic reaction with 4-amino-2,2,6,6-tetramethylpiperidine and their preparation CS253935B1 (en)

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