CS225049B1 - The sterically hindered piperidine on the base of alpha-monosubstituted butadiene acid - Google Patents

The sterically hindered piperidine on the base of alpha-monosubstituted butadiene acid Download PDF

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Publication number
CS225049B1
CS225049B1 CS420882A CS420882A CS225049B1 CS 225049 B1 CS225049 B1 CS 225049B1 CS 420882 A CS420882 A CS 420882A CS 420882 A CS420882 A CS 420882A CS 225049 B1 CS225049 B1 CS 225049B1
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CS
Czechoslovakia
Prior art keywords
monosubstituted
alpha
sterically hindered
base
hindered piperidine
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CS420882A
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Czech (cs)
Slovak (sk)
Inventor
Frantisek Prom Chem Vass
Zdenek Ing Csc Manasek
Jozef Ing Csc Luston
Original Assignee
Vass Frantisek
Manasek Zdenek
Luston Jozef
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Application filed by Vass Frantisek, Manasek Zdenek, Luston Jozef filed Critical Vass Frantisek
Priority to CS420882A priority Critical patent/CS225049B1/en
Publication of CS225049B1 publication Critical patent/CS225049B1/en

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Description

Vynález sa týká stéricky bráněných piperidínov na báze alfa-monosubstituovanej kyseliny butándiovej obecného vzorca IThe invention relates to sterically hindered piperidines based on alpha-monosubstituted butanedioic acid of the formula I

kde R značí metylová alebo etylová skupinu a ďalej sa vynález týká spfisobu ich přípravy.wherein R represents a methyl or ethyl group and the invention further relates to the preparation thereof.

Spfisob přípravy stéricky bráněných piperidínov na báze alfa-monosubstituovanej kyseliny butándiovej je založený na adícii 4-amino-2,2,6,6-tetrametylpiperidínu na dimetyl alebo dietylester kyseliny buténdiovej pri laboratórnej teplote, najvýhodnejěie v polárnom rozpúíťadle ako například v metanole.The method of preparing sterically hindered piperidines based on alpha-monosubstituted butanedioic acid is based on the addition of 4-amino-2,2,6,6-tetramethylpiperidine to dimethyl or diethylester of butenedioic acid at room temperature, most preferably in a polar solvent such as methanol.

Uvedené zlúčeniny patriace do skupiny stéricky bráněných amínov mfižu samotné pfisobiť ako světelné stabilizátory polymérov. Nevýhodou nízkomolekulových zlúčenín tejto skupiny je ich značná prchavosť, vypierateTnosť z Užitkového polyméru a toxicita. Přípravou polymérnyoh světelných stabilizátorov sa tieto nedostatky mfižu odstrániť. K tomuto účelu mfižu slúžiť látky, ktoré sú predmetom vynálezu.The compounds belonging to the group of sterically hindered amines can themselves be used as light stabilizers of polymers. The disadvantages of the low molecular weight compounds of this group are their high volatility, utility polymer washability and toxicity. By preparing polymeric light stabilizers, these drawbacks can be overcome. The substances which are the subject of the invention can be used for this purpose.

K roztoku 1,5526 g (0,01 mol) 4-amino-2,2,6,6-tetrametylpiperidínu v 10 ml metanolu sa pomaly prikvapkáva 1,7615 g (0,01 mol) dimetylesteru kyseliny maleinovej a zmes sa miega pri laboratórnej teplote 10 h. Po uplynulom Sase sa rozpúšťadlo odpaří a zbytok rozpustí v 20 ml chloroformu. Chloroformový roztok sa dókladne premyje vodou a vysuší nad bezvodým síranom sodným. Po odpaření rozpúšťadla sa zbytok íistí kryštalizéciou z petroléteru, aleboTo a solution of 1.5526 g (0.01 mol) of 4-amino-2,2,6,6-tetramethylpiperidine in 10 ml of methanol was slowly added dropwise 1.7615 g (0.01 mol) of dimethyl maleic ester and the mixture was stirred at room temperature. room temperature 10 h. After the period of time, the solvent was evaporated and the residue was dissolved in 20 ml of chloroform. The chloroform solution was washed thoroughly with water and dried over anhydrous sodium sulfate. After evaporation of the solvent, the residue is purified by crystallization from petroleum ether or

PříkladExample

sublimáoiou. Získá sa produkt v podobě priehl’adných ihličiek s teplotou topenia 101 až 102,5 °C. sublimáoiou. Obtained as transparent needles with a melting point of 101 to 102.5 ° C. Elementárna Elementary analýza pre θ,5Η28Ν2θ4analysis for θ, 5 Η 28 Ν 2θ4 vypočítané: calculated: 60,20 % C; 9,03 % H; 60.20% C; H, 9.03; 9,36 % N 9.36% N nájdené: found: 60,57 % C; 9,42 % H; 60.57% C; 9.42% H; 9,10 % N N, 9.10

IČ spektrum (chloroform):IR (chloroform):

v = 655, max v = 655, max 860, 880, 860 880 920, 920. 970, ' 970, ' I 020, I 020, I 030, 1 I 030.1 150, 1 180, 150, 1 180, 1 280, 1 280, 1 425 1 425 1 630, 1 630, 1 720, 2 1 720, 2 840, 840. 2 930, 2 930, 3 010, 3 010, 3 430, 3 430, 3 530 cm-1 3,530 cm -1

Claims (3)

PREDMET VYNÁLEZUOBJECT OF THE INVENTION 1. Stéricky bráněné piperidíny na báze alfa-monosubstituovanej kyseliny butándiovej obecného vzorca 1 kde R značí metylovú alebo etylovú skupinu.A sterically hindered piperidines based on alpha-monosubstituted butanedioic acid of the general formula 1 wherein R represents a methyl or ethyl group. 2. Spósob přípravy zlúčeniny obecného vzorca I podl’a bodu 1 , vyznačený tým, že sa na dimetyl alebo dietylester kyseliny buténdiovej pósobí 4-amino-2,2,6,6-tetrametylpiperidínom.2. A process for the preparation of a compound of the formula I as claimed in claim 1, wherein the butenedioic acid dimethyl or diethyl ester is treated with 4-amino-2,2,6,6-tetramethylpiperidine. 3. Spósob podTa bodu 2, vyznačený tým, že sa reakcia uskutočňuje pri laboratórnej teplote, najvýhodnejéie v polárnom rozpúšťadle ako například v metanole.3. A process according to claim 2, wherein the reaction is carried out at room temperature, most preferably in a polar solvent such as methanol.
CS420882A 1982-06-07 1982-06-07 The sterically hindered piperidine on the base of alpha-monosubstituted butadiene acid CS225049B1 (en)

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CS420882A CS225049B1 (en) 1982-06-07 1982-06-07 The sterically hindered piperidine on the base of alpha-monosubstituted butadiene acid

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CS420882A CS225049B1 (en) 1982-06-07 1982-06-07 The sterically hindered piperidine on the base of alpha-monosubstituted butadiene acid

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CZ299104B6 (en) * 2006-03-23 2008-04-23 Ústav makromolekulární chemie AV CR Copolymer stabilizer containing piperidine derivative, process for its preparation and use

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CZ299104B6 (en) * 2006-03-23 2008-04-23 Ústav makromolekulární chemie AV CR Copolymer stabilizer containing piperidine derivative, process for its preparation and use

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