CS254695B1 - 4-/2,3-epxypropoxy/-1,2,2,6,6-pentamethylpiperidine and process for preparing thereof - Google Patents
4-/2,3-epxypropoxy/-1,2,2,6,6-pentamethylpiperidine and process for preparing thereof Download PDFInfo
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- CS254695B1 CS254695B1 CS867369A CS736986A CS254695B1 CS 254695 B1 CS254695 B1 CS 254695B1 CS 867369 A CS867369 A CS 867369A CS 736986 A CS736986 A CS 736986A CS 254695 B1 CS254695 B1 CS 254695B1
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- pentamethylpiperidine
- pentamethyl
- hydroxypiperidine
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- 238000004519 manufacturing process Methods 0.000 title 1
- 238000002360 preparation method Methods 0.000 claims abstract description 8
- NWHNXXMYEICZAT-UHFFFAOYSA-N 1,2,2,6,6-pentamethylpiperidin-4-ol Chemical compound CN1C(C)(C)CC(O)CC1(C)C NWHNXXMYEICZAT-UHFFFAOYSA-N 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims abstract description 6
- 239000007864 aqueous solution Substances 0.000 claims abstract description 4
- 239000012071 phase Substances 0.000 claims abstract description 4
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims abstract description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims abstract description 3
- 239000008346 aqueous phase Substances 0.000 claims abstract description 3
- 150000003839 salts Chemical class 0.000 claims abstract 3
- 239000003054 catalyst Substances 0.000 claims abstract 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 8
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 claims description 4
- OHCHSGWRBYWCJD-UHFFFAOYSA-N 1,2,2,6,6-pentamethyl-4-(oxiran-2-ylmethoxy)piperidine Chemical compound C1C(C)(C)N(C)C(C)(C)CC1OCC1OC1 OHCHSGWRBYWCJD-UHFFFAOYSA-N 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 2
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 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
- 239000008096 xylene Substances 0.000 claims description 2
- 150000003738 xylenes Chemical class 0.000 claims description 2
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 claims 2
- 239000007809 chemical reaction catalyst Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
- 229920000642 polymer Polymers 0.000 abstract description 9
- -1 2,3-epoxypropoxy Chemical group 0.000 abstract description 6
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 abstract description 6
- 239000004611 light stabiliser Substances 0.000 abstract description 4
- 239000002904 solvent Substances 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
- 239000000243 solution Substances 0.000 abstract description 2
- 239000003381 stabilizer Substances 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000012074 organic phase Substances 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229920001155 polypropylene Polymers 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
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 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 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
- 241000405217 Viola <butterfly> Species 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
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000001816 cooling Methods 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
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Hydrogenated Pyridines (AREA)
Abstract
Riešenie sa týká 4-(2,3-epoxypropoxy)-l,- 2,2,6,6-pentametylpiperidínu vzorca I s spósobu jeho přípravy, ktorý spočívá v tom, že sa nechá reagovat l,2,2,6,6-pentametyl-4- -bydroxypiperidín vzorca II s epichlórhydrínom za Intenzívneho miešania v heterofázofom systéme, pričom jednu fázu vytvára vodný roztok alkalického hydroxidu a druhů fázu vytvára organické rozpúšťadlo nemiešstelné 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 polyméry a na přípravu polymérnych světelných stabilizátorov polyadičnými a kopolyadičnými reakciami, na přípravu polyéterov, kopolyéterov, polyesterov a kopolyesterov, alebo umožňuje naviazanie molekuly stabilizátora na vhodné skupiny na polymérnom reťazci.The solution relates to 4- (2,3-epoxypropoxy) -1, - Of 2,2,6,6-pentamethylpiperidine of formula I with the process his preparation, which lies in that 1,2,2,6,6-pentamethyl-4- -hydroxypiperidine of formula II with epichlorohydrin with intensive mixing in heterophasoph system, creating one phase an aqueous solution of alkali hydroxide and species the organic phase forms an immiscible solvent with an aqueous phase in the presence of an ionic salt type catalyst in temperature 10 ° C to 100 ° C. Compound of Formula I has 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 binding of the molecule stabilizer to suitable groups on the polymer chain.
Description
•0/ynplez;sa- ř_ týká 4- (2,3-epoxypropoxy) -'€,2,R',6ý6-peňťa,měty]pip^riďínu .4 sjpospbú ýjeho- přípravy. tn ·; .·*: .;z< /C• 0 / ynplez, self-° _ refers to 4- (2,3-epoxypropoxy) - '€ 2, R, 6Y6-penta methyl] pip ^ .4 to drive sjpospbú ýjeho- preparation. tn ·; . · *:. ; z </ C
Sféricky tienoné aminy patria v súčasnosti medzi najúčinnejšie svíOfei^é?; sjahili?áýory ,s pre polyméry [F. E./lťárrer, T-Makramol. Chem., 161, 595 (1980), F. Gugumus, Developimenťs 4n Polymer Stabilisation-l, ed. G. Scott, Applied Science Publishers, London, 197S, kap. 8, j. J. Usilton, A. E. Patel. Amer. Chem. Sec. Polym. Prep., 18 (1), 393 (1977)]. Sú to rozličné deriváty 2,2,6,6 tetraalkylpiperidínu, 1,2,2,6,6-pentaalkylpiporidínu, 2,2,6,6-tetraalkylpiperazínu alebo 7,15-diazadispiro[ 5,1,5,3) hexadekánu.At present, spherically shaded amines are among the most effective. silanes, s for polymers [FE / liter, T-Macramol. Chem., 161, 595 (1980), F. Gugumus, Developed 4n Polymer Stabilization-1, ed. G. Scott, Applied Science Publishers, London, 197S, Chap. 8, j. J. Usilton, AE Patel. Amer. Chem. Sec. Polym. Prep., 18 (1), 393 (1977)]. They are various derivatives of 2,2,6,6 tetraalkylpiperidine, 1,2,2,6,6-pentaalkylpiporidine, 2,2,6,6-tetraalkylpiperazine or 7,15-diazadispiro [5,1,5,3] hexadecane .
Tieto zlúčeniny inhibujú nežiadúce degradačné procesy, které prebiehajú pri interakci! světla a kyslíka s pclymérmi. Nevýhodou tejto triedy světelných stabilizátorov je vysoká prchavosť a extrahovatelnoisť nízkomolekulovýeb-derivátov z polymérov. Zlúčenina, ktorá je predmetom vynálezu obsahuje vioi svojej molekule reatívnu epoxidová skupinu. Přítomnost tejto skupiny v molekule světelného- stabilizátoru umožňuje přípravu vysokomolekulových. světelných slabilizátorov po-lyndičnými reakciami, přípravu polyéterov, kopolyétsrov, polyesíerov a kopolyestercv, ako- aj naviazaníe molekuly světelného stabilizátoru na vhodné skupiny na reťazci úžiíkového polyméru. Táto zlúčenina nebol-a doteija?,.popísaná. viodbornej literatuře.These compounds inhibit the undesirable degradation processes that occur during the interaction! light and oxygen with polymers. A disadvantage of this class of light stabilizers is the high volatility and extractability of low molecular weight β-derivatives from polymers. The compound of the invention contains a viola of its molecule a reactive epoxy group. The presence of this group in the light stabilizer molecule allows the preparation of high molecular weight. light diminisers by polymerization reactions, the preparation of polyethers, copolyethers, polyesters and copolyesters, as well as binding of the light stabilizer molecule to suitable groups on the useful polymer chain. This compound has not been described. viodbornej literatuře.
Podstatou vynálezu je 4-(2,3-epoxypropoxy ) -1,2,2,6,6-pentametylpiperidín vzorca I.The present invention provides 4- (2,3-epoxypropoxy) -1,2,2,6,6-pentamethylpiperidine of formula I.
H.f' -N /-4--0/0,,- CH-CM, h >.....\ / λ j \ ' ch,. c;·/ coH-N--4-O / O-CH-CM; c / · co
Podstatou vynálezu je ďalej sposob přípravy zlúčeniny vzorca 1, vyznačujúci sa tým, že l,2,2,6,6-pentametyl-4-hydroxypiperidm vzorca II lebo hydroxidu draselného- v koncentračnom rozmedzí/5-taž .^0 a druhu fázu v-ytvára organické róapůšťadio nemiešatefné s vodnou fázou, ako je například benzén, toluen ulebo-^y-l^yf.^ -přítomnosti katalyzátora ty, ‘ pú -óúievýeh solí,, ako je například tetrabutyla-mónium chlorid, tetrabutylamónium bromid, tetrabutylamónium hydrogénsíran alebo tetrabutylfoisfónium bromid, ktorý sa použije v množstve 1 ,až 10 mólu na. množstvo· zlúčeniny II v rozmedzí -teplot- 10 až 100 C. ί t ; '! , t ' - 1 The present invention further provides a process for the preparation of a compound of formula (1), characterized in that the 1,2,2,6,6-pentamethyl-4-hydroxypiperide of formula (II) or potassium hydroxide in the concentration range of (5-t. forms organic solvents which are immiscible with the aqueous phase, such as, for example, benzene, toluene or toluene. bromide to be used in an amount of 1 to 10 mol per. an amount of compound II in the temperature range of 10 to 100 ° C ; '! , t '- 1
Příklad 1Example 1
17.13 g (0,1 molu) l,2,2,6,6-pentametyl-4-hydroxypiperidínu, 3,22 g (0,01 mólu) tetrabutylamónium bromidu, 23 ml (0,25 mola) epichlórhydrínu. 25 ml benzénu a 25 ml 50 percentného vodného roztoku hydroxidu sodného sa intenzívně mieša pri labor-atórnej teplote 24 hodin. Potom sa oddělí organická vrstva, prepiera. sa vodou a solankou a vysuší sa bezvodým síranom sodným. Oddestiluje sa rozpúšťadlo a prebytočný epichlórhydrín na vákuovej odparke a získá sa nažítlá kvapalina, ktorá sa destiluje za vakua.. Odoberá sa írakcia bezfarebnej kvapaliny v teplotnom intervale 84 až 92 C pri tlaku 0,07 kPa. Výťažok je 15,5 g čistého produktu, t. j. 68 % teoretického- výtažku.17.13 g (0.1 mol) of 1,2,2,6,6-pentamethyl-4-hydroxypiperidine, 3.22 g (0.01 mol) of tetrabutylammonium bromide, 23 ml (0.25 mol) of epichlorohydrin. 25 ml of benzene and 25 ml of a 50% aqueous sodium hydroxide solution were stirred vigorously at room temperature for 24 hours. The organic layer is then 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 an edible liquid which was distilled under vacuum. Yield: 15.5 g of pure product, m.p. j. 68% of the theoretical yield.
Elementárna analýza pre:Elemental analysis for:
C13H25NO2 vypočítané:C13H25NO2 calculated:
C 68,68 %, IT 11,08 %, N 6,16 %, nájdené:C 68.68%, IT 11.08%, N 6.16%, found:
C.68,41 «/o, H 11,10 %, N 6,13 %.C.68.41%, H 11.10%, N 6.13%.
XH NMR.spektrum (CDCI3) (ppm);, NMR.spektrum; H (CDCl3) (ppm) ;,
0,93 (s,'—CH3,ax, 6H),0.93 (s, '- CH 3, ax, 6H),
1.08 (s, —CHs eq, 6H),1.08 (s, —CH3 eq, 6H),
1,23 až .2,02 (ID, —CPL·-, 4Hj,1.23 to .2.02 (ID, —CPL · -, 4Hj,
2.13 (s, CHs—N, 3H),2.13 (s, CH2-N, 3H),
2,45 až 2,332.45 to 2.33
CH, CH„ wCH, CH w
q >......0- U .7' reaguje s epichlórhydrínom za intenzívneho miešania v heterofázovom systéme, pričom jednu fázu vytvára vodný roztok alkalického hydroxidu, s výhodou hydroxidu sodného v koncentračnom rozmedzí 5 až 50 % aÍKV CH--CH,, Ť H //q is reacted with epichlorohydrin with vigorous stirring in a heterophasic system, one phase being formed by an aqueous solution of an alkali hydroxide, preferably sodium hydroxide, in a concentration range of 5 to 50% and CH 2 CH 2, , «H //
ΌΌ
2,92 až'3,25 ím, -Cij- Cl-!., . Ή-i ),2.92 to 3.25, -Cl-Cl-1. Ή-i)
OABOUT
3,35 -až 3,83 (m, —CH2—O-, =CH—O—, 3H).3.35 to 3.83 (m, --CH2 --O--, = CH - O--, 3H).
Příklad 2Example 2
8,56 g (0,05 mólu) l,2,2,6,6-pentametyl-4-hydroxypiperidínu, 0,85 g (0,0025 mólu) tetrabutylamónium hydrogensíranu, 11,5 g (0,125 mólu) epichlórhydrínu, 20 ml toluénu a 20 ml 30 %-ného vodného roztoku hydroxidu draselného sa intenzívně mieša při teplote 60 CC 10 hodin. Reakčná zmes sa spracuje rovnako· ako v přiklade 1. Výťažok je 8 g čistého· produktu, t. j. 70,5 % teoretického výtažku.8.56 g (0.05 mol) of 1,2,2,6,6-pentamethyl-4-hydroxypiperidine, 0.85 g (0.0025 mol) of tetrabutylammonium hydrogen sulfate, 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 60 DEG C. for 10 hours. The reaction mixture is worked up as in Example 1. The yield is 8 g of pure product, i.e. 70.5% of the theoretical yield.
Příklad 3Example 3
8,56 g (0,05 mólu) l,2,2,6,6-pentametyl-4-hydroxypiperidínu, 0,34 g (0,001 mólu) tetrabutylfosfónium bromidu, 5,55 g 10,06 mólu) epichlórhydrínu, 10 ml zmesi xylénov s destilačným rozmedzím 137 až 140 CC a 20 mililitrov vodného roztoku hydroxidu draselného sa intenzívně mieša pri teplote 100 stupňov Celzia 6 hodin. Po ochladnutí sa reakčná zmes spracuje rovnako ako v· příklade 1. Výťažok je 8,2 g čistého produktu, t. j. 72,1 % teoretického výtažku.8.56 g (0.05 mol) of 1,2,2,6,6-pentamethyl-4-hydroxypiperidine, 0.34 g (0.001 mol) of tetrabutylphosphonium bromide, 5.55 g of 10.06 mol) of epichlorohydrin, 10 ml of a mixture of xylenes having a distillation range of 137 DEG to 140 DEG C. and 20 ml of aqueous potassium hydroxide solution is vigorously stirred at 100 DEG C. for 6 hours. After cooling, the reaction mixture was worked up as in Example 1. The yield was 8.2 g of pure product, i.e. 72.1% of the theoretical yield.
Příklad 4Example 4
100 hmotnostných dielov nestabllizovaného práškovitého polypropylénu sa impregnuje v dichlórmetáne s 0,1 hmot. diela 2,6-di-terc.butyl-4-metylfenolu, 0,15 hmot. diela stearánu vápenatého a s 0,2 hmot. diela zlúčeniny, pripravenej podlá příkladu 1. Po odpaření rozpúšťadla sa zo zmesi vylisujú fólie o hrúbke 0,2 mm pri tlaku 20 MPa a teplote 190 °C po dobu 5 minút. Takto· připravené fólie sa ožiarujú ortutovou výbojkou o výkone 125 W vo vzdialenosti 7 cm od zclroja. Degradácia polyméru sa sleduje vývojom karbonylového pása v· infračervených spektra ch. Kým doba dosiahnutia karbonylového indexu 0,2 u čistého polypropylénu je 220 hodin, stabilizovaný polymér dosiahne túto hodnotu až po 2 000 hodinách.100 parts by weight of non-stabilized powdered polypropylene are impregnated in dichloromethane with 0.1 wt. % of 2,6-di-tert-butyl-4-methylphenol, 0.15 wt. % of calcium stearate and 0.2 wt. After evaporation of the solvent, 0.2 mm thick sheets are pressed from the mixture at 20 MPa at 190 ° C for 5 minutes. The films thus prepared are irradiated with a 125 W mercury lamp at a distance of 7 cm from the source. The degradation of the polymer is monitored by the development of the carbonyl band in the infrared spectra. While the time to reach the carbonyl index of 0.2 for pure polypropylene is 220 hours, the stabilized polymer does not reach this value until 2000 hours.
Claims (5)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS867369A CS254695B1 (en) | 1986-10-13 | 1986-10-13 | 4-/2,3-epxypropoxy/-1,2,2,6,6-pentamethylpiperidine and process for preparing thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS867369A CS254695B1 (en) | 1986-10-13 | 1986-10-13 | 4-/2,3-epxypropoxy/-1,2,2,6,6-pentamethylpiperidine and process for preparing thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS736986A1 CS736986A1 (en) | 1987-05-14 |
| CS254695B1 true CS254695B1 (en) | 1988-01-15 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS867369A CS254695B1 (en) | 1986-10-13 | 1986-10-13 | 4-/2,3-epxypropoxy/-1,2,2,6,6-pentamethylpiperidine and process for preparing thereof |
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| Country | Link |
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| CS (1) | CS254695B1 (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 CS867369A patent/CS254695B1/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 |
|---|---|
| CS736986A1 (en) | 1987-05-14 |
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