CS223422B1 - Addition of dihydroxy-derivatized tetrasubsulfonated piperazinedione and diisocyanate addition polymer - Google Patents

Abstract

The invention relates to an addition polymer based on a dihydroxy derivative of tetrasubstituted piperazinedione and diisocyanate and a method for its preparation. The essence of the method for preparing the addition polymer lies in the fact that in a dry solvent, a 2,3-dihydroxypropyl derivative of tetrasubstituted piperazinedione is treated with diisocyanate at elevated temperature. The invention is used for the preparation of an addition polymer suitable as a light stabilizer.

Description

The present invention relates to an addition polymer based on a dihydroxy derivative of tetrasubstituted piperazinedione and diisocyanate and to a process for its preparation.

The essence of the process for the preparation of the addition polymer is that in the dry solvent, the 2,3-dihydroxypropylderivative of the tetrasubstituted piperazinedione diisocyanate is treated at an elevated temperature.

The invention has use for the preparation of an addition polymer suitable as a light stabilizer.

The present invention relates to a piperazine-type polyurethane light stabilizer based on an addition polymer, which in the macromolecule comprises repeating structural units of the formula I

wherein n is an integer ranging from 2 to 50 and the invention further relates to a process for its preparation.

The process for preparing said addition polymer based on the dihydroxy derivative of tetrasubstituted piperazinedione and diisocyanate is based on the addition of a compound of formula II

HO-CH-CHn-OH 1.

CH _Z

With 2,4-toluene diisocyanate in the temperature range of 60-180 ° C in a dry organic solvent such as toluene, nitrobenzene, dioxane or dimethylformamide.

Sterically hindered amines are high-efficiency light stabilizers of many types of polymers. However, the use of low molecular weight substances of this type has some limitations. Their main drawbacks are: high volatility, considerable ability to migrate, easy extractability and, last but not least, good absorbability into cellular spaces of living organisms. The first three undesirable properties are the cause of their gradual loss from the utility polymer with a simultaneous loss of protective effect, first in its heat treatment, then in longer storage, and finally in its chemical cleaning or washing. The low cell wall penetration of living organisms due to the high toxicity of low molecular weight derivatives of spherically hindered amines excludes them from application in the stabilization of polymer materials in the food industry, possibly in the medical field. The reduction or elimination of disadvantageous properties presupposes the use of higher molecular weight oligomeric or polymeric light stabilizers with satisfactory tolerability, or the attachment of stabilizing structures to the chain of the useful polymer.

The piperazine-type light stabilizer belonging to the group of sterically hindered amines of the present invention can serve to suppress or eliminate spoiled deficiencies of the low-molecular-weight substances of the type. Example 1

To a solution of 0.9733 g (0.003 mol) of 15- (2,3-dihydroxypropyl) -7,15-diazadispiro [5,1,5,3] hexadecane-14,16-dione in 10 ml of dry dimethylformamide is added dropwise 0.1 ml. 5225 g (0.003 mol) of 2,4-toluenediisocyanate in 5 ml of dry dimethylformamide at 120 ° C. After further stirring the reaction mixture under reflux for 2 hours. allow the contents to cool and pour into cold water. Salting with sodium chloride gave a vacuum filter, washed with distilled water, dried at 1.3 Pa at 60 ° C. A powdery beige polymer having a melting point of 119 DEG -126 DEG C. and a molecular weight of 1006 (determined by thermoosmometry) is obtained.

Elemental analysis for C 26 H 34 N 4 O 6

Calculated: N = 11.21.

Found: N = 11.68.

IR (chloroform): _.lambda.max = 810, 1070, 1190, 1230, 1260, 1280,

1340, 1450, 1535, 1195, 1665, 1710, 2940, 3400 cm ^{@ -1} .

Example 2

To a solution of 0.9733 g (0.003 mol) of 15- (2,3-dihydroxypropyl) -7,15-diazadispiro [5,1,5,3] hexadecane-14,16-dione in 10 ml of dry nitrobenzene is added at a temperature of 0.5225 g (0.003 mol) of 2,4-toluenediisocyanate in 5 ml of dry nitrobenzene is added dropwise at 160 ° C. After further stirring the reaction mixture under reflux for 2 hours. The contents of the flask are allowed to cool and poured into methanol. The resulting polyurethane precipitate is vacuum filtered, dried at 1.3 Pa and at 60 ° C. A pulverulent light brown polymer having a melting point of 121 ^DEG- 132 ^DEG C. and a molecular weight of 1560 (determined by vapor phase osmometry) is obtained.

Elemental analysis for C 26 H 34 N 1 OS. Calculated: N = 11.21.

Found: N = 11.35.

IR (chloroform):

Umax = 855, 970, 1010, 1075, 1200, 1265,

1350, 1370, 1450, 1680, 1730, 2940 cm -1.

Claims (2)

After stirring the reaction mixture under cooling for 2 hours, the contents of the flask are not cooled and poured into methanol. The resultant polyurethane precipitate was vacuum-filtered, dried at 1.3 Pa, and dried. 60 ° Celsius. A light-brown powder powder polymer having a melting point in the range of 121 to 132 ° C and a molecular weight of 1560 (determined by vapor phase osmometry) is obtained. Elemental analysis for C 26 H 34 N 1 O 6. Calculated: N = 11.21. Found: N = 11.35. IR spectrum (chloroform): .nu.max = 855, 970, 1010, 1075, 1200, 1265, 1350, 1370, 1450, 1680, 1730, 2940 cm @ -1; SUBJECT MATTER A dihydroxyderidation additive polyamide tetrasubstituted piperazine and diisocyanate additive comprising repeating structural units of formula I where n is an integer ranging from 2 to 50. 2. A process for the preparation of an addition polymer comprising the dihydroxy derivative of the tetrasubstituted piperazine and diisocyanate according to claim 1, characterized in that the compound of formula II is treated with 2,4-toluene diisocyanate in a temperature range of 60 ° C to 180 ° C in dry organic in a solvent such as toluene, dioxane, nitrobenzene, diimethylformamide. Ho-cH-ci-fg-oH CHZ V'Nv '(I!)