CS252982B1 - Copolyesters on base of poly(ethylenebutandionate)containing 2,2,6,6-tetramethyl-4-piperidylamino- and octadecylamino groups - Google Patents

Description

The invention relates to copolyesters obtained on the basis of poly (ethylenebutanedionate) containing 2,2,6,6-tetramethyl-4-piperidylamino and octadecylamino groups and a process for their preparation.

Sterically hindered amines are high-efficiency light stabilizers of polymers. They inhibit undesirable radical processes that occur during photooxidation of polymers. A disadvantage of the low molecular weight compounds of this group is their considerable volatility and extractability, which results in their gradual loss from the useful polymer during processing, or later in storage, dry cleaning or washing.

These disadvantages are overcome by the present invention. The present invention relates to a copolyester obtained on the basis of a poly (ethylene-butanedionate), an octadecylamino group and a method for their addition of an amino- and octadecylamino group of the formula I

O 0

C-CW-CH ^ C-H-Chg-O · CH

NH ^C 18 ^H &

(i) where m-j have values of 2 to 100. The invention further provides a process for the preparation of a compound of formula I, characterized in that the poly (ethylene-2-butenedione) of formula II is

O O (1 1 where x is 2 to 100, simultaneously acts with 4-amino-2,2,6,6-tetramethylpiperidine of formula III

and n-octadecylamine IV at the appropriate molar ratios most preferably in chloroform, with stirring for 4 to 10 hours at reflux temperature.

An advantage of the present invention is an increase in the molecular weight of the stabilizer, which leads to a considerable elimination of the aforementioned drawbacks occurring in the low molecular weight compounds of this group.

Example 1

To a solution of 1.41 g of poly (ethylene-2-butenedic acid) II (M _n = 3200, 0.01 mole concentration of 2-butenedic acid) in 30 ml of chloroform was added 1.377 g (0.009 mol) of 4-amino-4-amine. 2,2,6,6-tetramethylpiperidine III and 0.269 g (0.001 mol) of n-octadecylamine IV, and the reaction mixture is stirred at reflux for 7 hours. After cooling, the solvent is removed by rotary evaporation and the oily residue is added. 50 ml of diethyl ether After standing for 1 hour and occasionally shaking the mixture, the precipitated solid residue is extracted several times with diethyl ether. nitrogen content of 8.83% and M _n - 2600, as determined by the VPO method.

IR spectrum (chloroform)

Vmax = 3,330, 2,980, 2,960, 1720, 1610, 1,450, 1,390, 1,380, 1,190 cnr ¹ Examples 2 to 6

Examples 2 to 6 show further results of the synthesis of the copolyesters of formula I by polymer-analogous reactions of poly (ethylene-2-butenedionate) II with 4-amino-2,2,6,6-tetramethylpiperldine III together with n-octadecylamine IV at appropriate molar ratios.

Example # Mole ratio Melting point ° C Yield M _n 10 ^-3 Time% N II: III: IV% of reaction h

2 1 0.8 : 0,2 62 to 71 91.7 2.52 7 7.37 3 1 0.7 : 0,3 63 to 70 84.6 2.32 7 6.80 4 1 0.6 : 0,4 59 to 65 81.7 2.09 4 5.81 5 1 0.5 : 0,5 53 to 60 87.3 1.73 7 5.28 6 1 0.4 : 0,6 50 to 58 76.8 2.03 9 4.92

The invention has applications for light stabilization of polymers, especially polyolefins, to eliminate the drawbacks found in low molecular weight sterically hindered amine compounds.

Claims (2)

SUBJECT We claim: Copolymers based on poly (ethylenebutanedionate) containing 2,2,6,6-tetramethyl-4-piperidylamino and octadecylamino groups of the formula I NH I ^C 18 ^h 3? (I): where m -j-n are 2 to 100. 2. A process for the preparation of a compound of formula (I) according to claim 1, characterized in that 4-amino-2,2,6,6-tetramethylpiperidine is simultaneously treated with poly (ethylene-2-butenedione) of formula (II) wherein x is 2 to 100. of formula III Most preferably, in the appropriate molar ratios, most preferably in chloroform, with stirring for 4 to 10 hours at reflux temperature.