CS264998B1 - 1,2,2,6,6-Pentamethyl-4-allyloxypiperidine - Google Patents
1,2,2,6,6-Pentamethyl-4-allyloxypiperidine Download PDFInfo
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- CS264998B1 CS264998B1 CS882671A CS267188A CS264998B1 CS 264998 B1 CS264998 B1 CS 264998B1 CS 882671 A CS882671 A CS 882671A CS 267188 A CS267188 A CS 267188A CS 264998 B1 CS264998 B1 CS 264998B1
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Abstract
Riešenie sa týká 1 , 2 , 2 , 6 , 6-pentametyl- . -4-alyloxypiperidínu. Uvedená zlúčenina sa připraví tak, že 1 , 2 , 2 , 6 , 6-pentametyl- -4-hydroxypiperidín reaguje s alylbromidom za intenzívneho miešania v heterofázovom systéme, pričom jednu fázu vytvára vodný roztok alkalického hydroxidu, s výhodou hydroxidu sodného alebo hydroxidu draselného a druhů fázu vytvára organické rozpúštadlo nemiešatelné s vodnou fázou za přítomnosti katalyzátora typ óniových solí v teplotnom rozmedzí 10 až 100 °C. Zlúčenina má použitie ako světelný stabilizátor pre polyméry alebo je medzi- produktom pre přípravu polymérnych světelných stabilizátorov polymerizač- nými alebo kopolimerizačnými reakciami.The solution relates to 1,2,2,6,6-pentamethyl-. -4-allyloxypiperidine. The compound is prepared by reacting 1,2,2,6,6-pentamethyl- -4-hydroxypiperidine with allyl bromide under intensive stirring in a heterophase system, whereby one phase is formed by an aqueous solution of an alkali hydroxide, preferably sodium hydroxide or potassium hydroxide, and the second phase is formed by an organic solvent immiscible with the aqueous phase in the presence of a catalyst such as onium salts in the temperature range of 10 to 100 °C. The compound is used as a light stabilizer for polymers or is an intermediate for the preparation of polymer light stabilizers by polymerization or copolymerization reactions.
Description
264998 2 . Vynález sa týká 1,2,2,6,6-pentametyl-4-alyloxypiperidínu.
Stérický tienené aminy patria v súČastnosti medzi najúčinnejšie světelné stabilizátorypre polyméry (F. E. Karrer, Makromol, Chem., 181, 595 (1980), F: Gugumus, Developmentsin Polymer Stabilisation-1, ed. G. Scott, Applied Science Publishers, London, 1$79, kap. 8, J. J. Usilton, A. R. Patel, Am. Chem. Soc. Polym. Prep., 18 (1), 393 (1977)). Sú torozličné deriváty 2,2,6,6-tetrametylpiperidínu, 1,2,2,6,6-pentaalkylpiperidínu, 2,2,6,6--tetraalkylpiperazínu alebo 7,15-diazadispiro[5,1,5,3]hexadekánu. Tieto zlúčeniny inhibujúnežiadúce degradačné procesy, ktoré prebiehajú pri interakcii světla a kyslíka s polymérmi.Nevýhodou tejto triedy světelných stabilizátorov je vysoká prchavost a extrahovatelnostnízkomolekulových derivátov z polymérov. Zlúčenina, ktorá je predmetom vynálezu, obsahujevo svojej molekule funkčnú nenasýtenú vSzbu. Přítomnost tejto skupiny v molekule světelnéhostabilizátora umožňuje přípravu vysokomolekulových světelných stabilizátorov polymerizácioualylovej skupiny alebo jej kopolymerizáciou s inými nenasýtenými monomérmi. Táto zlúčeninanebola doteraz popísáná v odbornéj literatúre.
Podstatou vynálezu je 1,2,2,6,6-pentametyl-4-alyloxypiperidín vzorca I. H3C CH,
Va H3c-N 2—o-ch2-ch-ch2 Ál· H3c ch3 (i)
Spósob přípravy zlúčeniny I spočívá v tom, že 1,2,2,6,6-pentametyl-4-hydroxypiperidínvzorca II
reaguje s alylbromidom za intenzívneho miešania v heterofázovom systéme, pričom jednu fázuvytvára vodný roztok alkalického hydroxidu, s výhodou hydroxidu sodného v koncentračnomrozmedzí 5 až 50 % alebo hydroxidu draselného v koncentračnom rozmedzí 5 až 70 % a druhůfázu vytvára organické rozpúštadlo nemiešajúce sa s vodnou fázou, ako je benzén, toluénalebo xylény, za přítomnosti katalyzátore typu óniových solí, ako je tetrabutylamónium chlorid,tetrabutylamónium bromid, tetrabutylamónium hydrogénsíran alebo tetrabutylfosfónium bromid,ktorý sa použije v množstve 1 až 10 mol % na množstvo zlúčeniny II v rozmedzí teplót 10až 100 °C. Předmětná látka sa móže použit ako světelný stabilizátor pre polyméry alebo je medzi-produktom pre přípravu polymérnych světelných stabilizátorov polymerizačnými alebo kopolymerizačnými reakciami. Příklad 1 5,14 g (0,03 nol) 1,2,2,6,6-pentametyl-4-hydroxypiperidínu, 3,99 g (0,033 mol) alylbromidu,1,93 g (0,006 mol) tetrabutylamónium bromidu, 10 ml benzénu a 15 ml 50 %-ného vodného roztokuhydroxidu sodného sa intenzívně mieša pri izbovej teplote 24 hodin. Potom sa oddělí organickávrstva, ktorá sa prepiera vodou a solankou a vysuší sa bezvodým síranom sodným. Oddestilujesa rozpúštadlo a zbytok pri analýze pomocou vysokoúčinnej kvapalinovej chromatografie naobrátnej fáze ukazuje iba jediný pík. Získajú sa 4 g produktu, t. j. 63 % teoretického výtažku.
264998 2. The invention relates to 1,2,2,6,6-pentamethyl-4-allyloxypiperidine.
Steric shielded amines are among the most effective light stabilizers for polymers (FE Karrer, Makromol, Chem., 181, 595 (1980), F: Gugumus, Developments Polymer Stabilization-1, G. Scott, Applied Science Publishers, London, 1). $ 79, Chapter 8, JJ Usilton, AR Patel, Am Chem Soc Polym Prep, 18 (1), 393 (1977). There are torial 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 the undesirable degradation processes that occur with the interaction of light with oxygen with the polymers. The disadvantage of this class of light stabilizers is the high volatility and extractable molecular weight derivatives of polymers. The compound of the invention contains functional unsaturation in its molecule. The presence of this group in the light-stabilizer molecule allows the preparation of high molecular weight light stabilizers of the polymerization alkyl group or by copolymerization thereof with other unsaturated monomers. This compound has so far been described in the literature.
The present invention provides 1,2,2,6,6-pentamethyl-4-allyloxypiperidine of formula I.
Va H3c-N 2-o-ch2-ch-ch2 Al · H3c ch3 (i)
The method for the preparation of Compound I is that 1,2,2,6,6-pentamethyl-4-hydroxypiperidine Formula II
reacts with allyl bromide with vigorous stirring in a 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% or potassium hydroxide in a concentration range of 5 to 70%, and the species forms an organic solvent not mixed with the aqueous phase, such as is benzene, toluene or xylenes, in the presence of an onion salt catalyst such as tetrabutylammonium chloride, tetrabutylammonium bromide, tetrabutylammonium hydrogen sulfate or tetrabutylphosphonium bromide, which is used in an amount of 1 to 10 mol% per amount of compound II in the temperature range of 10 to 100 ° C. The subject matter can be used as a light stabilizer for polymers or is an intermediate product for the preparation of polymeric light stabilizers by polymerization or copolymerization reactions. Example 1 5.14 g (0.03 mol) of 1,2,2,6,6-pentamethyl-4-hydroxypiperidine, 3.99 g (0.033 mol) of allyl bromide, 1.93 g (0.006 mol) of tetrabutylammonium bromide, 10 ml of benzene and 15 ml of 50% aqueous sodium hydroxide solution are stirred vigorously at room temperature for 24 hours. The organic layer is then separated and washed with water and brine and dried over anhydrous sodium sulfate. The solvent is distilled off and the residue in the high performance liquid chromatography analysis shows only a single peak. 4 g of product are obtained, i.e. 63% of the theoretical yield.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS882671A CS264998B1 (en) | 1988-04-20 | 1988-04-20 | 1,2,2,6,6-Pentamethyl-4-allyloxypiperidine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS882671A CS264998B1 (en) | 1988-04-20 | 1988-04-20 | 1,2,2,6,6-Pentamethyl-4-allyloxypiperidine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS267188A1 CS267188A1 (en) | 1988-10-14 |
| CS264998B1 true CS264998B1 (en) | 1989-09-12 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS882671A CS264998B1 (en) | 1988-04-20 | 1988-04-20 | 1,2,2,6,6-Pentamethyl-4-allyloxypiperidine |
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1988
- 1988-04-20 CS CS882671A patent/CS264998B1/en unknown
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| CS267188A1 (en) | 1988-10-14 |
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