CS254698B1 - 4- (2,3-epoxyprnpoxy) -2,2,6,6-tetramethylpiperidine and its preparation - Google Patents

4- (2,3-epoxyprnpoxy) -2,2,6,6-tetramethylpiperidine and its preparation Download PDF

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CS254698B1
CS254698B1 CS867374A CS737486A CS254698B1 CS 254698 B1 CS254698 B1 CS 254698B1 CS 867374 A CS867374 A CS 867374A CS 737486 A CS737486 A CS 737486A CS 254698 B1 CS254698 B1 CS 254698B1
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Jozef Luston
Edita Smieskova
Frantisek Vass
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Jozef Luston
Edita Smieskova
Frantisek Vass
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Abstract

Ríešoule sa lýka 4-(2,3-epoxypropoxy)-2,- 2,8,6-tctrametylpjperidínu vzorca I a spůsobu jeho přípravy, ktorý spočívá v tom, že sa nechá reagovat 2,2,6,6-teirainetyl-4-hydroxypiperidín vzorca Ií s epichlórhydrínom za intsozívneho miešania v heterofázovom systéme, pričom jednu fázu vytvára vodný roztok alkalického hydroxidu a druhů fázu vytvára organické rozpúšťadlo nemiešatel'- né s vodnou fázou za přítomnosti katalyzátora typu óniových solí v teplotnom rozmedzí 10 až 100 °C. Zlúčenina vzorca I má použitie ako světelný stabilizátor pre polymery a na přípravy polymérnych světelných stabilizátorov polyadičnými a kopolyadičnými reakciami, na přípravy polyéterov, kopolyéterov, polyesterov a kopolyesterov, alebo umožňuje naviazanie molekuly stabilizátore na vhodné skupiny na polymérnom reťazci.The invention relates to 4-(2,3-epoxypropoxy)-2,- 2,8,6-tetramethylpiperidine of formula I and to a method for its preparation, which consists in reacting 2,2,6,6-tetramethyl-4-hydroxypiperidine of formula I 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 an onium salt type catalyst 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

Vynález sa týká 4-(2,3-epoxypropoxy)-2,2,6,6-tetrametylpiperidínu a spósobu jeho. přípravy.The invention relates to 4- (2,3-epoxypropoxy) -2,2,6,6-tetramethylpiperidine and a method thereof. of preparation.

Stéricky tienené aminy patria v súčasnosti medzi najúčinnejšie světelné stabilizátory pre polyméry [F. E. Karrer, Makromol. Chem. 181, 595 (1980), F. Gugumus, Developments in Polymer Stabilisation-1, ed. G. Scott, Applied Science Publishers, London, 1979, kap. 8. J. J. Usilton, A. R. Patel., Amer. Chem. Soc. Polym. Prep., 18 (1), 393 (1977). Sú to rozličné deriváty 2,2,6,6-tetrametylpiperidínu, 1,2,2,6,6-pentaalkylpiperidínu, 2,2,6,6-tetraalkylpiperazínu alebo 7,15-diazadispiro[5,l,5,3]hexadekánu. Tieto zlúčeniny inhibujú nežiadúce degradačné procesy, ktoré prebiehajú pri interakcii světla a kyslíka s polymérmi. Nevýhodou tejto triedy světelných stabilizátorov je vysoká prchavosť a extrahovatelnosť nízkomolekulových derivátov z polymérov. Látka, ktorá je predmetom vynálezu, obsahuje vo svojej molekule reaktívnu epoxidovú skupinu. Přítomnost tejto skupiny v molekule světelného stabilizátora umožňuje přípravu vysokomolekulových světelných stabilizátorov polyadičnými a kopolyadičnými reakciami, přípravu polyéterov, kopolyéterov, polyesterov a kopolyesterov, ako aj naviazanie molekuly světelného, stabilizátora na vhodné skupiny na polymérnom reťazci. Táto. zlúčenina nebola doteraz popísaná v odbornej literatúre.Sterically shielded amines are currently among the most effective light stabilizers for polymers [F. E. Karrer, Makromol. Chem. 181, 595 (1980), F. Gugumus, Developments in Polymer Stabilization-1, ed. G. Scott, Applied Science Publishers, London, 1979, Chap. 8. J. J. Usilton, A. R. Patel., Amer. Chem. Soc. Polym. Prep., 18 (1), 393 (1977). They are various derivatives of 2,2,6,6-tetramethylpiperidine, 1,2,2,6,6-pentaalkylpiperidine, 2,2,6,6-tetraalkylpiperazine or 7,15-diazadispiro [5,1,5,3] hexadecane. These compounds inhibit undesirable degradation processes that occur in the interaction of light and oxygen with polymers. A disadvantage of this class of light stabilizers is the high volatility and extractability of low molecular weight derivatives from polymers. The substance of the invention contains a reactive epoxy group in its molecule. The presence of this group in the light stabilizer molecule enables the preparation of high molecular weight light stabilizers by polyaddition and copolyaddition reactions, the preparation of polyethers, copolyethers, polyesters and copolyesters, as well as the attachment of the light stabilizer molecule to suitable groups on the polymer chain. This. the compound has not been previously described in the literature.

Podstatou vynálezu je 4-(2,3-epoxypr.o,poxyj-Ž^^.B-tetrametylpiperidín vzorca I.The present invention provides 4- (2,3-epoxypropoxy) -2- [beta] -tetramethylpiperidine of formula I.

medzi 5 až 70 % a druhů Fázu vytvára organické rozpúšfadlo nemiešajúce sa s vodnou fázou, ako je například benzén, toluén alebo xylény, za přítomnosti katalyzátora typu óniových solí, ako je například tetrabutylamónium chlorid, tetrabutylamónium bromid, tetrabutylaimónium hydrogénsíran alebo tetrabutylfosfónium bromid, ktorý sa použije v množstve 1 až 10 mól % na množstvo zlúčeniny II v rozmedzí teplot 10 až 100 CC.between 5 to 70% and of the species The phase forms an organic solvent not mixed with the aqueous phase, such as benzene, toluene or xylenes, in the presence of an onium salt type catalyst such as tetrabutylammonium chloride, tetrabutylammonium bromide, tetrabutylaimonium hydrogen sulphate or tetrabutylphosphonate used in an amount of 1 to 10 mol% for the amount of compound II in the temperature range of 10 to 100 ° C.

Příklad 1Example 1

7,85 g (0,05 móluj 2,2 6,6-tetrametyl-4-hydroxypiperidínu, 1,61 g (0,005 móluj tetrabutylamónium bromidu, 23 g (0,25 mólu) epichlórhydrínu, 20 ml benzénu a 20 ml 50 %ného vodného roztoku hydroxidu sodného sa intenzívně mieša pri laboratórnej teplote 24 hodin. Potom sa oddělí organická vrstva, prepiera sa vodou a solankou a vysuší sa bezvodým síranům sodným. Oddestiluje sa rozpúšťadlo a prebytočný epichlórhydrín na vákuovej odparke a získá sa nažltlá kvapalina, ktorá sa vákuovo destiluje.7.85 g (0.05 mol) of 2,2,6,6-tetramethyl-4-hydroxypiperidine, 1.61 g (0.005 mol of tetrabutylammonium bromide), 23 g (0.25 mol) of epichlorohydrin, 20 ml of benzene and 20 ml of 50% The organic layer was separated, washed with water and brine, and dried over anhydrous sodium sulfate. The solvent and excess epichlorohydrin were distilled off in a vacuum evaporator to give a yellowish liquid which was vacuum dried. distilled.

Odoberá sa frakcia bezfarebnej kvapaliny v teplotnom intervale 95 až 105 CC pri tlaku 0,2 kPa. Výťažok je 6,0 g čistého, produktu, t. j. 56,3 % teoretického výtažku.A colorless liquid fraction is collected over a temperature range of 95-105 ° C at 0.2 kPa. Yield: 6.0 g of pure product, i.e. 56.3% of theory.

Elementárna analýza pre:Elemental analysis for:

C12H23NO2 vypočítané:C12H23NO2 calculated:

67,56 % C, 10,87 % H, 6,57 % N,H, 10.87; N, 6.57.

C ΜC H ί v,, J •y /C ΜC H ί v ,, J • y /

T~\ v / XO (IIT ~ \ v / X O (II

Podstatou vynálezu je ďalej spósob přípravy zlúčeniny vzorca I, vyznačujúci sa tým, že 2,2,6,6-tetrametyl-4-hydroxypiperidín vzorca II nájdené:The present invention further provides a process for the preparation of a compound of formula I, characterized in that 2,2,6,6-tetramethyl-4-hydroxypiperidine of formula II is found:

66,95 % C, 10,47 % H, 6,51 % N.H, 10.47; N, 6.51.

1H, NMR spektrum (CDCk) 1 H, NMR spectrum (CDCl 3)

Ó (ppmj:Δ (ppmj:

1,05 (s, — CH3 ax, 6H),1.05 (s, --CH 3 ax, 6H),

1,08 (s, —CH3 eq, 6H),1.08 (s, —CH 3 eq, 6H),

1,50 až 2,08 (m, —CH2—, 4H), 2,42 až 2,80 fin,1.50 to 2.08 (m, --CH2 -, 4H), 2.42 to 2.80 fin,

2,88 až 3,302.88 to 3.30

O-H reaguje s epichlórhydrínoím za intenzívneho miešania v heterofázovom systéme, pričom jednu fázu vytvára vodný roztok alkalického hydroxidu, s výhodou hydroxidu sodného v koncentračnom rozmedzí 5 až 50 % alebo hydroxidu draselného v koncentračnom roz3,35 až 4,00 (m, — CH2—O—, =CH—O—, 3H).The OH reacts with epichlorohydrin under vigorous stirring in a heterophasic system, one phase forming an aqueous solution of an alkaline hydroxide, preferably sodium hydroxide in a concentration range of 5 to 50% or potassium hydroxide in a concentration range of 3,35 to 4,00 (m, - CH2 - O). -, .dbd.CH - O--, 3H).

Příklad 2Example 2

7,85 g (0,05 móluj 2,2,6,6-tetrametyl-4-hyd5 roxypíperidínu, 0,85 g (0,0025 molu) tetrabutylamónium hydrogénsíranu, 11,5· g (0,125 molu) epichlórhydrínu, 20 ml toluenu a 20 mililitrov 30 %-ného vodného roztoku hydroxidu draselného· sa intenzívně mieša pri teplote 50 °C 16 hodin. Reakčná zmes sa spracuje rovnako ako v příklade 1. Výťažok je 6,8 g čistého produktu, t. j. 64 % teoretického výtažku.7.85 g (0.05 mol) of 2,2,6,6-tetramethyl-4-hydroxy-roxypiperidine, 0.85 g (0.0025 mol) of tetrabutylammonium hydrogen sulphate, 11.5 g (0.125 mol) of epichlorohydrin, 20 ml toluene and 20 ml of a 30% aqueous potassium hydroxide solution are stirred vigorously at 50 DEG C. for 16 hours, and the reaction mixture is worked up as in Example 1. The yield is 6.8 g of pure product, i.e. 64% of theory.

Příklad 3Example 3

7,85 g (0,05 molu) 2,2,6,6-tetrametyl-4-hydroxipiperidínu, 0,34 g (0,001 molu) tetrabutylfosfónium bromidu, 5,55 g (0,06 molu) epichlórhydrínu, 10 ml zmesi xylénov s desiilačným rozmedzím 137 až 140 °C a 20 mililitrov 60 %-ného vodného· roztoku hydroxidu draselného sa intenzívně mieša pri teplote 100 °C po dobu 6 hodin. Po· ochladnutí sa reakčná zmes spracuje rovnako ako v7.85 g (0.05 mol) of 2,2,6,6-tetramethyl-4-hydroxipiperidine, 0.34 g (0.001 mol) of tetrabutylphosphonium bromide, 5.55 g (0.06 mol) of epichlorohydrin, 10 ml of the mixture The xylenes having a distillation range of 137 to 140 ° C and 20 ml of a 60% aqueous potassium hydroxide solution are vigorously stirred at 100 ° C for 6 hours. After cooling, the reaction mixture was worked up as in the reaction

PREDMETSUBJECT

Claims (5)

5 .23 46 9 8 roxypíperidínu, 0,85 g (0,0025 molu) tetra-butylamónium hydrogénsíranu, 11,5; g (0,125molu) epichlórhydrínu, 20 ml toluenu a 20mililitrov 30 %-ného vodného roztoku hyd-roxidu draselného' sa intenzívně mieša priteplote 50 °C 16 hodin. Reakčná zmes sa spra-cuje rovnako ako v příklade 1. Výťažok je6,8 g čistého produktu, t. j. 64 % teoretické-ho výtažku. Příklad 3 7,85 g (0,05 molu) 2,2,6,6-tetrametyl-4--hydroxipiperidínu, 0,34 g (0,001 molu) tet-rabutylfosfónium bromidu, 5,55 g (0,06 mo-lu) epichlórhydrínu, 10 ml zmesi xylénov sdesiilačným rozmedzím 137 až 140 °C a 20mililitrov 60 %-ného vodného' roztoku hydro-xidu draselného sa intenzívně mieša pri tep-loto 100 °C po dobu 6 hodin. Po· ochladnutísa reakčná zmes spracuje rovnako ako v PREDMET 1. 4-(2,3-epoxypropoxy)-2,2,6,6-tetrametyl-piperidín vzorca I. r · i C MCr. s CM, — h J í f)0.82 g (0.0025 mol) tetra-butylammonium hydrogen sulphate, 11.5; g (0.125 mol) of epichlorohydrin, 20 ml of toluene and 20 ml of a 30% aqueous potassium hydroxide solution are stirred vigorously at 50 DEG C. for 16 hours. The reaction mixture was worked up as in Example 1. Yield: 6.8 g of pure product, i.e. 64% of theory. Example 3 7.85 g (0.05 mol) of 2,2,6,6-tetramethyl-4-hydroxipiperidine, 0.34 g (0.001 mol) of tetrabutylphosphonium bromide, 5.55 g (0.06 mol) (ll) of epichlorohydrin, 10 ml of a xylene mixture of a 137- 140 ° C xylene range, and 20 ml of a 60% aqueous potassium hydroxide solution were vigorously stirred at 100 ° C for 6 hours. After cooling, the reaction mixture is treated as in SUBJECT 1. 4- (2,3-epoxypropoxy) -2,2,6,6-tetramethylpiperidine of the formula (I). with CM, - h J í f) 2. Sposob přípravy 4-(2,3-epoxypropoxy)--2,2,6,6-tetrametylpiperidínu vzorca I podlábodu 1, vyznačujúci sa tým, že 2,2,6,6-tetra-metyl-4-hydroxypiperidín vzorca II2. A process for the preparation of 4- (2,3-epoxypropoxy) -2,2,6,6-tetramethylpiperidine of the formula I according to claim 1, wherein the 2,2,6,6-tetra-methyl-4-hydroxypiperidine of the formula II příklade 1. Výťažok je 7,2 g čistého produk-tu, t. j. 67,6 % teoretického výtažku.Příklad 4 100 hmotnostných dielov nestabilizované-ho práškovitého polypropylénu sa impreg-nuje v dichlórmetáne s 0,1 hmot. diela 2,6--di-terc.butyl-4-metylfenolu, 0,15 hmot. die-la stearanu vápenatého a s 0,2 hmot. dielazlúčeniny, pripravenej podlá příkladu 1. Po,odpaření rozpúšťadla sa zo zmesi vylisujúfólie o hrúbke 0,2 mm pri tlaku 20 MPa ateplote 190 °C po. dobu 5 niinút. Takto při-pravená fólie sa ožarujú ortuťovou výbojkouo výkone 125 W vo vzdialenosti 7 cm odzdroja. Degradácia polyméru sa sleduje vý-vojom karbonylového pása v infračervenýchspektrách. Kým doba dosiahnutia karbony-lového indexu 0,2 u čistého polypropylénuje 220 hodin, stabilizovaný polymér dosiahnetáto hodnotu až po 1 800 hodinách. VYNÁLEZU reaguje s epichlórhydrínom za intenzívneho'miešania v heterofázovom systéme, pričomjednu fázu vytvára rodný roztok alkalické-ho hydroxidu a druhů fázu vytvára organic-ké rozpúšťadlo nemiešatelné s vodnou fá-zou, za přítomnosti batalyzátora typu auto-vých solí s teplotnom rozmedzí 10 až 100 °C.EXAMPLE 1 Yield 7.2 g of pure product, i.e. 67.6% of theoretical yield. EXAMPLE 4,100 parts by weight of unstabilized polypropylene powder are impregnated in dichloromethane with 0.1% by weight of the theoretical product. 2,6-di-tert-butyl-4-methylphenol, 0.15 wt. of calcium stearate and 0.2 wt. of the compound of Example 1. After evaporation of the solvent, a 0.2 mm thick film was pressed from the mixture at a pressure of 20 MPa and a temperature of 190 ° C. 5 min. The thus prepared film is irradiated with a mercury discharge lamp with a power of 125 W at a distance of 7 cm from the source. The degradation of the polymer is monitored by developing a carbonyl band in infrared spectra. While the carbonyl index time of 0.2 for pure polypropylene was 220 hours, the stabilized polymer reached a value after 1800 hours. THE INVENTION reacts with epichlorohydrin under intensive mixing in a heterophasic system, forming one phase of the alkaline hydroxide solution in one phase and generating the phase phase organic solvent immiscible with the aqueous phase, in the presence of an auto salt type catalyst with a temperature range of 10 to 100 ° C. 3. Sposob podl'a bodu 2, vyznačujúci satým,, že sa ako alkalický hydroxid použijehydroxid sodný v komcentračnom rozmedzí5 až 50 % alebO' hydroxid draselný v kon-centračnom rozmedzí 5 až 70 ’%.3. A process according to claim 2, wherein sodium hydroxide is used as the alkali hydroxide in a concentration range of 5 to 50% or potassium hydroxide in a concentration range of 5 to 70%. 4. Sposob podlá bodu 2, vyznačujúci satým, že sa ako organické rozpúšťadlo nemie-šatelné s vodnou fázou použije benzén, to-luén alebo xylény.4. A process according to claim 2, wherein benzene, toluene or xylenes are used as the aqueous phase-immiscible organic solvent. 15. Sposob podlá bodu 2, vyznačujúci satým, že sa ako katalyzátor reakcie použijúóniové soli, ,ako tetrabutylamónium chlorid,tetrabutylamónium bromid, tetrabutylamó-nium hydrogénsíran alebo tetrabutylfosfó-nium bromid v množstve 1 až 10 mól %,vztiahnuté na množstvo zlúčeniny 2,2,6,6--tetrametyl-4-hydroxypiperidínu. ř (i i15. A process as claimed in claim 2, wherein the reaction catalyst used is a sodium 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 2.2. 6,6-tetramethyl-4-hydroxypiperidine. (i
CS867374A 1986-10-13 1986-10-13 4- (2,3-epoxyprnpoxy) -2,2,6,6-tetramethylpiperidine and its preparation CS254698B1 (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0634449A3 (en) * 1993-07-13 1995-09-27 Ciba Geigy Ag Polyether with sterically hindered amine side chains as stabilizing agents.

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0634449A3 (en) * 1993-07-13 1995-09-27 Ciba Geigy Ag Polyether with sterically hindered amine side chains as stabilizing agents.

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