CS230349B1 - Dioctadecylester of 2-/l7,15-diazadispiro-/l5,1,5,3/p-hexadecan-15-yl/propanedienic acid and method of preparing same - Google Patents

Description

The present invention relates to 2- [7,15-diazadispiro- (5,1,5,3) -hexadecan-15-yl] -propanedioic acid dioctadecyl ester and a process for its preparation.

Sterically hindered amines are high-efficiency light stabilizers of plastics. A disadvantage of the low molecular weight compounds of this group is their considerable washability and toxicity.

This disadvantage is overcome by the present invention. The present invention provides 2- [7,15-diazadispiro- (5,1,5,3) -hexadecan-15-yl] -propanedioic acid dioctadecyl ester of formula I c = o

-CH I

C-0 1

The present invention further provides a process for the preparation of a compound of formula I which is characterized in that the dioctadecyl ester of 2-bromopropanedioic acid II

O O

CH 3 (CH 2] i7-O-C-CH-C-O- (CH2) 17CH3

I

Br (II) acts with 7,15-diazadispiro- (5,1,5,3) -hexadecane of formula III

for 24 hours at 15-25 ° C, with stirring in dimethylformamide or benzene in the presence of triethylamine.

The advantage of the present invention is to increase the molecular weight and introduce the α230349 keel chains with a larger number of carbon atoms into the stabilizer molecule, which in addition to substantially eliminating said drawbacks and improving the compatibility with utility polymers, especially polyolefins.

Example 1

To a solution of 1.35 g (0.006 mol) of 7,15-diazadispiro- (5,1,5,3) hexadecane in 16 ml of dimethylformamide was added dropwise with stirring

4.13 g (0.006 mol) of 2-bromopropanedioic acid dioctadecyl ester] in 10 ml of dimethylformamide. The mixture was stirred at 15 ° C for 24 hours, then poured into water, basified with sodium hydroxide solution and extracted with chloroform. The extract was washed twice with water and concentrated in vacuo. The product was treated with charcoal in hexane, filtered through a thin pad of silica gel and crystallized from bexane. A white crystalline solid was obtained with a melting point of 60-62 ^° C in 48% yield and a molecular weight of 825 (determined thermoosmometrically).

Elemental analysis for C53H96O4N2 Calculated:

% C, 77.13;% H, 11.92;% N, 3.39.

% C, 76.91;% H, 12.14;% N, 3.09. = 1000, 1075, 1145, 1280, 1450, 1710,

2840, 2900, 3260 cm ⁴ .

Example 2

To a solution of 1.34 g (0.006 mol) of 7,15-diazadispiro (5,1,5,3) -hexadecane and 1 ml of triethylamine in 20 ml of benzene was added dropwise a solution of 2-bromopropanedioic acid dioctadecyl ester in 20 ml of benzene. The mixture was stirred at 25 ° C for 24 hours, then the resulting solid was dissolved in saturated potassium carbonate solution and the solution was extracted with ether. The ether extracts were combined with the obtained filtrate and dried over anhydrous sodium sulfate. The solvents were evaporated and the product was crystallized from ethyl alcohol. The product obtained had a melting point of 61-62 ° C and a molecular weight of 833 (determined thermoosmometrically).

Elemental analysis for C53H96O4N2 Calculated:

% C, 77.13;% H, 11.72;% N, 3.39.

% C, 76.88;% H, 11.83;% N, 2.99%. IR (chloroform) vmax = 1000, 1075, 1145, 1280, 1480, 1710,

2840, 3260 cm ⁴ .

The invention has application for the preparation of a light stabilizer for polymers, in particular polyolefins.

Claims (2)

keel chains with a greater number of carbon atoms into the stabilizer molecule, which in addition to substantially eliminating the abovementioned drawbacks and improving the compatibility with utility polymers, especially polyolefins. Example 1 To a solution of 1.35 g (0.006 mol) of 7,15-diaza-displro- (5,1,5,3-hexadecane in 16 ml of dimethylformamide) was added dropwise 4.13 g (0.006 mol) of dioctadecyl esters of acid. The mixture was stirred for 24 hours at 15 ° C, then poured into water, basified with sodium hydroxide solution and extracted with chloroform, and the extract was washed twice with water and concentrated in vacuo. boiled with activated charcoal in hexane, filtered through a thin pad of silica gel and crystallized from hexane, the white crystalline solid having a melting point of 60-62 ° C in 48% yield and a molecular weight of 825 (determined thermo-isometric). % H, 11.92; N, 3.39. Found: C, 76.91; H, 12.14; N, 3.09% (chloroform) .nu.max. = 1000, 1075, 1145, 1280 , 1450, 1710, 2840, 2900, 3260 cm -1 Example 2 To a solution of 1.34 g (0.006 mol) of 7,15-diaza-dispiro (5,1,5,3) of hexadecane and 1 ml of triethyl amine in 20 ml of benzene was added dropwise to a solution of dioctadecyl 2-bromopropanedioate in 20 ml of benzene. The mixture was stirred at 25 ° C for 24 hours, then dissolved in saturated potassium carbonate solution and extracted extensively with ether. The ethereal extracts were combined with the obtained filtrate and dried over anhydrous sodium sulfate. The solvents were evaporated and the product was crystallized from ethyl alcohol. The product obtained had a melting point of 61-62 ° C and a molecular weight of 833 (determined thermo-isometric). Elemental analysis for C 53 H 96 O 4 N 2 Calculated: C, 77.13; H, 11.72; N, 3.39. Found: C, 76.88; H, 11.83; N, 2.99% (chloroform) .nu.max = 1000, 1075. 1145, 1280, 1480, 1710, 2840, 3260 cm @ -1. The invention has utility in the preparation of a light stabilizer in polymers, in particular polyolefins. PREDMEI VYNALEZU 1. Dioctadecyl 2- [7,15-diaza-dispiro- (5,1,5,3) -hexadecan-15-yl] -propanedioic acid formula IC = O-CH 1 C-O ° "CC? C CA CA CH 3 (CH 2) 17 -O-C-CH-C-O- (CH 2) 17 CH 3 Br (II) provides 7,15-diazadispiro- (5,1,5,3-hexadecane) of Formula III 2. A process for preparing the compound of formula (I) according to claim 1, characterized in that the di-octadecyl ester of 2-bromopropanedione (II) is stirred in dimethylformamide or benzene in the presence of triethylamine for 24 hours at 15-25 ° C. .