CS232347B1 - Processing of alpha,alpha-bis(7,15-diazadispiro(5,1,5,3)hexadecan-15-yl)adipic acid - Google Patents

Description

The invention relates to dialkyl α, α'-bis (7,15-diazadispiro [5,115,3] hexadecan-15-yl) adipic acid, and a process for the preparation thereof.

The sterically hindered amines are high-efficiency low molecular weight compounds of this group, light stabilizers, and their considerable superheat and polymers. The downside is washability.

These disadvantages are overcome by the present invention. The present invention provides a .alpha.,. Alpha .'-bis (7,15-diazadispiro [5,1,5,3] hexadecan-15-yl) adipic acid dialkyl ester of formula (I)

(1) wherein R is methyl or characterized in that the ethyl group and further a process for the preparation of the compound of formula (I) are converted to the dialkyl α, α-dibromo-adipate of the formula II

RO

C - CH - CH, I ² Br

CH, -CH-C

I \

Br OR (11) wherein R is methyl or ethyl of formula III, is treated with 7,15-diazadispiro (5,1,5,3) hexadecane,

H

AI

N

H (111) for 24 h at 15-25 ° C, with stirring in dimethylformamide or benzene in the presence of triethylamine.

An advantage of the present invention is, on the one hand, an increase in the molecular weight of the stabilizer itself and, on the other hand, the possibility of preparing a polymeric light stabilizer, which in addition to substantially eliminating the aforementioned drawbacks occurring with the low molecular weight compounds.

EXAMPLE

To a solution of 2,22 g (0,01 mol) of 7, 5-diazadispiro [5,1,5,3] hexadecane in 20 ml of dry dimethylformamide, a solution of 3.6 g is slowly added dropwise at about 20 ° C with stirring. (0.01 mol) diethyl α, α'-dibromadipate in 15 ml of dry dimethylformamide. The mixture was further stirred for 5 hours, then poured into 60 ml of water and basified with 40% sodium hydroxide solution. It is extracted three times with chloroform, the combined extracts are dried over anhydrous sodium sulphate and the solvent is evaporated. The remaining solid was recrystallized from eanol. The product is obtained in the form of a white crystalline solid, m.p. 89-92 ° C.

Elemental analysis for ^G 3a ^H 66 ^{I <} 4 ⁰ 4

Calculated: C = 70.99 «H = 10.35% N = 8.71%

Not Found: C = 70.93% H = 10.40% N = 8.80%

Example 2

To a solution of 2.22 g (0.01 mol) of 7,15-diazadispiro [5.1, 5.3] hexadecene and 1.7 ml of triethylamine in 40 ml of dry benzene is slowly added dropwise at about 20 ° C with stirring. solution of 3,6 g (0,01 mol) of diethyl α, α, dibromo-adipate in 20 ml of dry benzene.

The reaction mixture is allowed to stir at the same temperature for 24 h. The resulting solid is filtered off with suction, dissolved in saturated potassium carbonate solution and extracted thoroughly with ether. The benzene filtrate and the ether extracts were combined, dried over anhydrous sodium sulfate, and the solvents were evaporated after filtration. The solid residue is recrystallized from ethanol to give the product as a white crystalline solid, m.p. 89-92 ° C.

Elemental analysis for ^C 38 ^H 66 ^N 4 ° 4

Calculated: C = 70.99% H = 10.35% N = 8.17%

Found: C = 70.85% H = 10.30% N = 8.66%

IR (chloroform):

ν = 860, 920, 945, 970, 1,020, 1,075, 1,090, 1,155, 1,170, 1,230, 1,275, 1,285,

-i

340, 1,370, 1,450, 1,720, 2,860, 2940, 3,180, 3,360, 3,470 cm '

H-NMR spectrum (d-chloroform):

S = 1.00 (singlet, 1H), 1.28 (triplet, 6H), 1.50 (broad band, 20H), 2.23 (broad band, 8H), 2.83 (multiplet, 4H), 3 43 (broad br, 2H), 4.18 (quartet, 4H) ppm

The invention has application in the polymer chemistry for preparing light stabilizers of polymers.

Claims (2)

The reaction mixture was allowed to stir at the same temperature for 24 h. The resulting solid was filtered off with suction, dissolved in saturated potassium carbonate solution and extracted with ether. The benzene filtrate and ethereal extracts were combined, dried over sodium sulphate and the solvents evaporated after filtration. The solid residue was recrystallized from ethanol to give the product as a white crystalline solid, mp 89-92 ° C. H, 10.35; N, 8.17. Found: C = 70.85%, H = 10.30%, N = 8.66; chloroform: v = 860, 920, 945, 970, 1 020, 1 075, 1 090, 1 155, 1 170, 1 230, 1 275, 1 285, 1 340, 1 370, 1 450, 1 720, 2860, 2940, 3180, 3160, 3470 cm -1 H-NMR spectrum (d-chloroform): S = 1.00 (singlet, 1H), 1.28 (triplet, 6H), 1, 50 (broad band, 20H), 2.23 (broad band, 8H), 2.83 (multiplet, 4H), 3.43 (broad band, 2H), 4.18 (quartet, 4H) ppm. polymer chemistry for the preparation of polymer light stabilizers. SUBJECT OF THE INVENTION 1. Dialkyl ether of α, α'-bis (7,15-diazadispiro [5,1,5,3] hexadecan-15-yl) adipic acid of general formula I wherein R is methyl or ethyl. 2. A process for the preparation of a compound of the general formula (I) according to claim 1, characterized in that the dialkyl ether of a, .alpha.-dibromodipiperic acid of the formula II is O / 11 / OR wherein R is methyl or ethyl. [5,1,5,3] Hexadecane Formula III ZC - CH - CHO - CHO - CH - C4 - J RO Br Br for 24 hours at 15 to 25 in the presence of triethylamine. with stirring in dimethylphonamide or benzene / 111 /