CS254698B1 - 4-/2,3-epoxypropoxy/-2,2,6,6-tetramethylpiperidine and process for preparing thereof - Google Patents
4-/2,3-epoxypropoxy/-2,2,6,6-tetramethylpiperidine and process for preparing thereof Download PDFInfo
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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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- tetramethylpiperidine
- epoxypropoxy
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- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 title abstract description 4
- 238000004519 manufacturing process Methods 0.000 title 1
- 229920000642 polymer Polymers 0.000 claims abstract description 9
- 238000002360 preparation method Methods 0.000 claims abstract description 8
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims abstract description 7
- -1 2,3-epoxypropoxy Chemical group 0.000 claims abstract description 6
- 239000012071 phase Substances 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 5
- 239000003960 organic solvent Substances 0.000 claims abstract description 4
- 239000008346 aqueous phase Substances 0.000 claims abstract description 3
- 239000003054 catalyst Substances 0.000 claims abstract description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims abstract description 3
- 238000003756 stirring Methods 0.000 claims abstract description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 claims description 4
- STPRYPLHPUMXIF-UHFFFAOYSA-N 2,2,6,6-tetramethyl-4-(oxiran-2-ylmethoxy)piperidine Chemical compound C1C(C)(C)NC(C)(C)CC1OCC1OC1 STPRYPLHPUMXIF-UHFFFAOYSA-N 0.000 claims description 3
- VDVUCLWJZJHFAV-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidin-4-ol Chemical compound CC1(C)CC(O)CC(C)(C)N1 VDVUCLWJZJHFAV-UHFFFAOYSA-N 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims description 3
- 239000008096 xylene Substances 0.000 claims description 3
- 150000003738 xylenes Chemical class 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 238000006731 degradation reaction Methods 0.000 claims description 2
- 238000011161 development Methods 0.000 claims description 2
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- 239000004743 Polypropylene Substances 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- 229920001155 polypropylene Polymers 0.000 claims 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 claims 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 claims 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 claims 1
- 235000013539 calcium stearate Nutrition 0.000 claims 1
- 239000008116 calcium stearate Substances 0.000 claims 1
- 230000015556 catabolic process Effects 0.000 claims 1
- 239000007809 chemical reaction catalyst Substances 0.000 claims 1
- 230000008020 evaporation Effects 0.000 claims 1
- 238000001704 evaporation Methods 0.000 claims 1
- 239000011888 foil Substances 0.000 claims 1
- 238000002329 infrared spectrum Methods 0.000 claims 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims 1
- 229910052753 mercury Inorganic materials 0.000 claims 1
- 239000004611 light stabiliser Substances 0.000 abstract description 6
- 238000006243 chemical reaction Methods 0.000 abstract description 3
- 229920001634 Copolyester Polymers 0.000 abstract description 2
- 229920000728 polyester Polymers 0.000 abstract description 2
- 229920000570 polyether Polymers 0.000 abstract description 2
- 239000003381 stabilizer Substances 0.000 abstract 2
- 125000000129 anionic group Chemical group 0.000 abstract 1
- 239000007788 liquid Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- ZOSPIRSWAQIPSU-UHFFFAOYSA-N 7,15-diazadispiro[5.1.5^{8}.3^{6}]hexadecane Chemical compound C1CCCCC21NC1(CCCCC1)CNC2 ZOSPIRSWAQIPSU-UHFFFAOYSA-N 0.000 description 1
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
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- Hydrogenated Pyridines (AREA)
- Compositions Of Macromolecular Compounds (AREA)
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.Ríešoule is bast 4- (2,3-epoxypropoxy) -2, - 2,8,6-tetramethylpiperidine of formula I and the process his preparation, which lies in that 2,2,6,6-Tiraphinetyl-4-hydroxypiperidine is reacted of formula Ii with epichlorohydrin with intsive stirring in heterophasic system, with one phase being aqueous alkaline hydroxide solution and species phase generates an organic solvent immiscible with the aqueous phase in the presence of a catalyst of the anionic salt type in the temperature range 10 to 100 ° C. The compound of formula I is of use as a light stabilizer for polymers and for the preparation of polymeric light polyaddition and copolyadic stabilizers reactions, for the preparation of polyethers, copolyethers, polyesters and copolyesters, or allows 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)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS867374A CS254698B1 (en) | 1986-10-13 | 1986-10-13 | 4-/2,3-epoxypropoxy/-2,2,6,6-tetramethylpiperidine and process for preparing thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS867374A CS254698B1 (en) | 1986-10-13 | 1986-10-13 | 4-/2,3-epoxypropoxy/-2,2,6,6-tetramethylpiperidine and process for preparing thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS737486A1 CS737486A1 (en) | 1987-05-14 |
| CS254698B1 true CS254698B1 (en) | 1988-01-15 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS867374A CS254698B1 (en) | 1986-10-13 | 1986-10-13 | 4-/2,3-epoxypropoxy/-2,2,6,6-tetramethylpiperidine and process for preparing thereof |
Country Status (1)
| Country | Link |
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| CS (1) | CS254698B1 (en) |
Cited By (1)
| 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. |
-
1986
- 1986-10-13 CS CS867374A patent/CS254698B1/en unknown
Cited By (1)
| 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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| Publication number | Publication date |
|---|---|
| CS737486A1 (en) | 1987-05-14 |
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