CS226926B1

CS226926B1 - A-monosubstituted butanedioic acid sterically hindered piperazines

Info

Publication number: CS226926B1
Application number: CS421182A
Authority: CS
Inventors: Jozef Ing Csc Luston; Frantisek Prom Chem Vass; Zdenek Ing Csc Manasek
Original assignee: Luston Jozef; Vass Frantisek; Manasek Zdenek
Priority date: 1982-06-07
Filing date: 1982-06-07
Publication date: 1984-04-16

Abstract

Vynále-z sa týká stéricky bráněných piperazínov na báze α-monosubstituovanej kyseliny butándiovej obecného vzorca kde R značí alkylovú skupinu s počtom ató- mov uhlíka 1 až 18 a spdsobu ich přípravy. Spdsob prípravé stéricky bráněných piperazínov na báze a-monosubatituovanej kyseliny butándiovej je založený na adícii 7,15- -diazadispiro[ 5,1,5,3jhexadekánu na dialkylester kyseliny 2-buténdiovej, kde alkyl obsahuje 1 až 18 atómov uhlíka pri laboratorně) teplote najvýhodnejšie v polárnom rozpúšťadle, ako například metanole, etanole atd1.The invention relates to sterically hindered piperazines based on α-monosubstituted butanedioic acid of the general formula where R denotes an alkyl group with the number of carbon atoms from 1 to 18 and the method of their preparation. The process for the preparation of sterically hindered piperazines based on α-monosubstituted butanedioic acid is based on the addition of 7,15-diazadispiro[5,1,5,3jhexadecane to the dialkyl ester of 2-butenedioic acid, where the alkyl contains 1 to 18 carbon atoms at room temperature, preferably in a polar solvent, such as methanol, ethanol, etc.1.

Description

CZECHOSLOVAK SOCIALISTIC

(19)

DESCRIPTION FOLLOWING COPYRIGHT CERTIFICATE!) 226926 (11) (Bl)

OftAD for InventionsA DISCOVERY (22) Enrolled 07 06 82 (21) (PV 4211-82) (51) Int. Cl? / C 07 D 241 / 38O— (40) Published 25 02 83 (45) Published 15 05 86 (75)

The inventor

LUSTO JOZEF ing. CSc., BRATISLAVA, VAŠŠ FRANTIŠEK prom. Chem., HUMENNÉ, MAŇÁSEK ZDENĚK ing. CSc., BRATISLAVA (54) Sterically hindered α-monosubstituted butanedioic acid-based piperazines 1

The invention relates to sterically hindered α-monosubstituted butanedioic acid-based piperazines of the formula

wherein R represents an alkyl group having from 1 to 18 carbon atoms and a method for preparing the same.

The preparation of sterically hindered α-monosubatated butanedioic acid-based piperazines is based on the addition of 7,15-diazadlspiro [5,1,5,3 Jhexadecane to the dialkyl 2-butenedioic ester, where 1 up to 18 carbon atoms at room temperature, most preferably in a polar solvent such as methanol, ethanol and the like.

Said compounds belonging to the group 2 of sterically hindered amines can themselves act as light stabilizers for polymers. A disadvantage of the low molecular weight compounds is their considerable volatility, elimination from the useful polymer and toxicity. These drawbacks can be avoided by the preparation of polymeric light stabilizers. For this purpose I can serve the substances of the invention. Example: To a solution of 2.22 g (0.01 mol) of 7,15-diazadiospiro [5,1,5,3] hexadecane in 30 ml of methanol, 1.7615 g (0.01 mol) of maleic dimethyl ester is slowly added dropwise. and the mixture was stirred at room temperature for 10 h. After time, the solvent was evaporated and the residue was crystallized from petroleum ether. A white crystalline product is obtained with a melting point of 102.5-103 ° C.

Elemental analysis for

Calculated: C = 65.57 H - 9.29%, N = 7.65%, Found: C = 66.05%, H = 9.47%, N = 7.43%. 228926

Claims

1. Sterically hindered α-monosubstituted piperazines (fatty butanedioic acid of the general formula

Where R is an alkyl group having a carbon number of 1 to 18.

2. A process for the preparation of sterically hindered piperazines based on .alpha.-monosubstituted butanedioic acid according to claim 1, characterized in that 7,15-diazadispiro [5.1] is applied to the 2-butenedioic acid dialkyl ester of alkyl having 1 to 18 carbon atoms. 5.3] hexadecane.

3. The method of claim 2, wherein the reaction is carried out at room temperature in a polar solvent such as methanol, ethanol.