CS254695B1 - 4- (2,3-epoxypropoxy) -1,2,2,6,6-pentamethylpiperidine and its preparation - Google Patents

Abstract

The solution relates to 4-(2,3-epoxypropoxy)-1,- 2,2,6,6-pentamethylpiperidine of formula I and a method for its preparation, which consists in reacting 1,2,2,6,6-pentamethyl-4- -hydroxypiperidine of formula II with epichlorohydrin under intensive stirring in a heterophase system, whereby one phase is formed by an aqueous solution of an alkali hydroxide and the second phase is formed by an organic solvent immiscible with the aqueous phase in the presence of a catalyst of the onium salt type in the temperature range of 10 to 100 ° C. The compound of formula I is used as a light stabilizer for polymers and for the preparation of polymer light stabilizers by polyaddition and copolyaddition reactions, for the preparation of polyethers, copolyethers, polyesters and copolyesters, or enables the attachment of the stabilizer molecule to suitable groups on the polymer chain.

Description

254695 '^ Vyn ^ hBz; . ·. sa; relates to 4- (2,3-epoxypropoxy) -2,2,6,6,6-pentahydrate, and to the preparation thereof. tu ·; Ln.

Spherically thienated amines are currently most effective at present; silage, silage, polymers [F. Chem., 180, 595 (1980), F. Gugumus, Deve-lopunen 4n Polymer Stabilization-1, ed. G. Scott, Applied Science Publishers, London, 197S, Chap. 8,]. J. Usilton, A. E. Patel. Amer.Ghem. Sec. Polym. Prep., 18 (1), 393 (1977)] Various derivatives of 2,2,6,6 tetraalkylpiperidine, 1,2,2,6,6-pentaalkylpiperidine, 2,2,6,6- tetraalkylpiperazine but 7,15-diazadiospiro [5,1,5,3] hexadecane.

These compounds inhibit the unwanted degradation processes that occur during inter-action! light and oxygen with polymers. The disadvantage of this class of light stabilizers is the high volatility and extractability of low molecular weight derivatives of polymer. The compound of the present invention contains a reatable epoxide group via its molecule. Presence of this group in the light stabilizer molecule. allows the preparation of high molecular weight. the light stabilizers by polyaddition reactions, preparative polyethers, copolyethers, polyesters and co-polyester derivatives, as well as the attachment of a light stabilizer molecule to suitable utility polymer moieties. This compounded dotpi: and?,. viodbprnej literatura.

The subject of the invention is 4- (2,3-epoxypropoxy) -1,2,2,6,6-pentamethylpiperidine of formula I. H.f: -N > 4N ' - Cl-1-CC,

4 λ ..... / C / CH ,. "Π /

The invention furthermore relates to a process for the preparation of a compound of formula 1, characterized in that the 1,2,2,6,6-pentamethyl-4-hydroxypiperidine formula II or the potassium hydroxide in the concentration range of δ 5 and ω 0 and the phase-forming organic solvent is immiscible. with an aqueous phase, such as benzene, toluene or carbonyl, the presence of a catalyst. tetrafluorolammonium chloride, tetrabutylammonium bromide, tetrabutylammonium hydrogen sulphate or tetrabutylfoisphonium bromide, which is used in an amount of 1 to 10 moles per. the amount of compound II in the range of -10 to 100 ° C. '! Example 1 17.13 g (0.1 mol) of 1,2,6,6-pentamethyl-4-hydroxypiperidine, 3.22 g (0.01 mol) of tetrabutylammonium bromide, 23 ml (0, 25 moles of epichlorohydrin. 25 ml of benzene and 25 ml of a 50% aqueous solution of sodium hydroxide are vigorously stirred at room temperature for 24 hours. Then the organic layer is separated, washed. with water and brine, and drying with anhydrous sodium sulfate, distilling off the solvent and excess epichlorohydrin in a vacuum evaporator to obtain a warm liquid which is distilled under vacuum. The colorless liquid fraction is recovered at 84-40 ° C. 92 C at 0.07 kPa. The yield is 15.5 g of pure product, i.e. 68% of theory.

Elemental analysis for C 13 H 25 NO 2 calculated: C 68.68%, H 11.08%, N 6.16%, found C.68.41%, H 11.10%, N 6.13%. 1 H NMR spectrum (CDCl 3) (PPmh 0.93 (s, CH 3, ax, 6H), 1.08 (s, - CH 3 eq, 6H), 1.23 to .2.02 (: m, - CPL · -, 4H), 2.13 (s, CH 3 --N, 3H), 2.45 to 2.33 CH, CH "wq - <4> ...... C" reacts with epichlorohydrin under intensive mixing in heterophasic system wherein one phase is formed by an aqueous solution of alkali hydroxide, preferably sodium hydroxide, in a concentration range of 5 to 50% by weight, &quot; C11-C20 &lt; 0 &gt;-C; j · Cl -!, II)),

From 3.35 to 3.83 (m, --CH2 --O--, = CH - O ', 3H).

Claims (5)

1. 4- (2,3-epoxypropoxy) -1,2,2,6,6-pentamethylpiperidine of formula I. te teto 2. A process for the preparation of 4- (2,3-epoxypropoxy) -1,2,2,6,6-pentamethylpiperidine of the formula I according to claim 1, characterized in that 1,2,2,6,6-pentamethyl-4-hydroxypiperidine of the formula II in _x ³ te reacts with epichlorliydrin with vigorous stirring in a heterophasic system, one phase forming an aqueous solution of alkaline hydroxide and the other phase forming an organic solvent immiscible with the aqueous phase in the presence of an onium salt type catalyst at a temperature range of 10 to 100 ° C. 3. A process according to claim 2, wherein the alkali hydroxide is sodium hydroxide in a concentration range of 5 to 50% or potassium hydroxide in a concentration range of 5 to 70%. 4. The process of claim 2 wherein benzene, toluene or xylenes are miscible with the aqueous solution as the organic solvent. 5. The process of claim 2, wherein the reaction catalyst used is an onium salt such as tetrabutylammonium chloride, tetrabutylammonium bromide, tetrabutylammonium hydrogen sulfate or tetrabutylphosphonium bromide in an amount of 1 to 10 mol% based on the amount of compound 1,2,2,6 , 6-pentamethyl-4-hydroxypiperidine.