CS216274B1 - 15-+l2,3-epoxypropyl+p-7,15-diazadispiro+l5,1,5,3+p hexadekan-14,16-dion and method of making the same - Google Patents
15-+l2,3-epoxypropyl+p-7,15-diazadispiro+l5,1,5,3+p hexadekan-14,16-dion and method of making the same Download PDFInfo
- Publication number
- CS216274B1 CS216274B1 CS345680A CS345680A CS216274B1 CS 216274 B1 CS216274 B1 CS 216274B1 CS 345680 A CS345680 A CS 345680A CS 345680 A CS345680 A CS 345680A CS 216274 B1 CS216274 B1 CS 216274B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- diazadispiro
- epoxypropyl
- hexadekan
- dion
- making
- Prior art date
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- 238000004519 manufacturing process Methods 0.000 title 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 3
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- NWRYOVCYBJWBEC-UHFFFAOYSA-N 3-oxohexadecanal Chemical class CCCCCCCCCCCCCC(=O)CC=O NWRYOVCYBJWBEC-UHFFFAOYSA-N 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- WCQBVYMYTSEPKC-UHFFFAOYSA-N 7,15-diazadispiro[5.1.5^{8}.3^{6}]hexadecane-14,16-dione Chemical compound N1C2(CCCCC2)C(=O)NC(=O)C21CCCCC2 WCQBVYMYTSEPKC-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000004611 light stabiliser Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- -1 polypropylene Polymers 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 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 description 1
- 150000001412 amines Chemical class 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
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000012667 polymer degradation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
Description
Vynález sa týká 15-(2,3-epoxypropyl)-7,15-diazadispiro [5, 1, 5, 3] hexadelkán -14,16-dión nasledujúceho vzorca:The invention relates to 15- (2,3-epoxypropyl) -7,15-diazadispiro [5,1,5,3] hexadecan-14,16-dione of the following formula:
a sposobu jeho přípravy.and the way it is prepared.
Sposob přípravy zlúčeniny, ktorá nie je známa z literatúry, je založený na reakcii 1-chlór-2,3-epoxypropánu a 7,15-diazadispiro [5, 1, 5, 3] hexadekán-14,16-diónom.The preparation of a compound not known in the literature is based on the reaction of 1-chloro-2,3-epoxypropane and 7,15-diazadispiro [5,1,5,3] hexadecane-14,16-dione.
Uvedená zlúčenina patriaca do skupiny sféricky bráněných amínov može sama osebe plnit íunkciu světelného stabilizátora. Nevýhodou nízkomolekulových látok tejto skupiny je ich lahká vypieratelnosť. Příprava polymérneho světelného stabilizátora tento nedostatok odstraňuje. K tomuto účelu može slúžiť látka, ktorá je predmetom vynálezu.The compound belonging to the group of spherically hindered amines can in itself serve as a light stabilizer. A disadvantage of the low molecular weight compounds of this group is their easy washability. The preparation of a polymeric light stabilizer removes this drawback. The substance of the invention can be used for this purpose.
Příklad 1Example 1
K 5,77 g (0,02 molu) draselnej soli 7,15-diazadispiro- [5, 1, 5, 3] hexadekán-14,16-diónu v 60 ml bezv. dimetylformamidu sa za stálého miešania pri teplote okolo 80 °C prikvapkáva v priebéhu 1/2 až 1 hodiny roztok 2,03 g (0,022 molu) l-chlór-2,3-epoxypropánu v 20 ml bezvodého dimetylformamidu. Zmes sa ďalej zohrieva a mieša po dobu 3 hodin a nechá sa ochladil. Vyextrahuje sa třikrát éterom a spojené éterické extrakty sa dokladné premyjú vodou, vysušia bezv. Na2SO4 a éter sa odpaří. Získaný zvyšok sa prekryštalizuje z etanolu. Získá sa produkt v podobě bielych ihličiek a t.t. = 87—90 °C. Elementárna analýza pre C17H26N2O3:To 5.77 g (0.02 mole) of 7,15-diazadispiro- [5, 1, 5, 3] hexadecane-14,16-dione potassium salt in 60 ml of anhydrous salt. of dimethylformamide, while stirring at about 80 ° C, a solution of 2.03 g (0.022 mol) of 1-chloro-2,3-epoxypropane in 20 ml of anhydrous dimethylformamide is added dropwise over a period of 1/2 to 1 hour. The mixture was further heated and stirred for 3 hours and allowed to cool. It is extracted three times with ether and the combined ether extracts are thoroughly washed with water, dried freely. Na 2 SO 4 and ether are evaporated. The residue is recrystallized from ethanol. The product is obtained in the form of white needles and mp = 87-90 ° C. Elemental analysis for C 17 H 26 N 2 O 3:
i·and ·
Vypočítané:calculated:
C = 66,64 %; H = 8,56 %; N = 9,14 % Nájdené:C = 66.64%; H = 8.56%; N = 9.14% Found:
C = 66,46 %; H = 8,59 %; N = 9,16 %C = 66.46%; H = 8.59%; N = 9.16%
IC spektrum (CHCI3).IC spectrum (CHCl 3).
Vmax = 840, 980, 1070, 1195, 1270, 1340, 1450, 1680, 1220, 2940, 3020V max = 840, 980, 1070, 1195, 1270, 1340, 1450, 1680, 1220, 2940, 3020
Příklad 2Example 2
100 hmotnostných dielov nestahilizované!ho práškovitého polypropylénu sa impregnovalo v dichlórmetáne s 0,1 hmot. dielmi 2,6-di-terc. butyl-4-metylfenolu, 0,15 hmot. dielmi stearanu vápenatého a s 0,2 hmot.100 parts by weight of non-sterilized powdered polypropylene were impregnated in dichloromethane with 0.1 wt. parts 2,6-di-tert. butyl-4-methylphenol, 0.15 wt. % of calcium stearate and 0.2 wt.
dielmi zlúčeniny, pripravenej podía příkladuparts of the compound prepared according to the example
1. Po odpaření rozpúšťadla sa zo zmesi vylisovali fólie o hrúbke 0,2 mm pri tlaku 20 MPa a teplote 190 °C po dobu 30 sekúnd. Tesne před lisováním sa vzorky ešte predohrievali 1 minútu pri teplote 190 °C. Fólie sa ozařovali ©rtuťovou výbojkou o výkone 125 W vo vzdialenosti 7 cm od zdroja a ako filter sa použil 1,6 hmot. % roztok síranu meďnatého. Degradácia polyméru sa sledovala vývoj om ihydroperoxidového a karbonylového pásu v infračervených spektrách. Kým doba dosiahnutia karbonylového indexu 0,2 u čistého polypropylénu bola 480 hodin, stabilizovaný polymér nedosiahol tuto hodnotu ani za 3000 hodin.1. After evaporation of the solvent, 0.2 mm thick films were pressed from the mixture at a pressure of 20 MPa and a temperature of 190 ° C for 30 seconds. Just before pressing, the samples were preheated for 1 minute at 190 ° C. The films were irradiated with a 125 W Mercury lamp at a distance of 7 cm from the source and a 1.6 wt. % copper sulfate solution. The polymer degradation was followed by the development of the omhydroperoxide and carbonyl bands in the infrared spectra. While the time of reaching the carbonyl index of 0.2 for pure polypropylene was 480 hours, the stabilized polymer did not reach this value even after 3000 hours.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS345680A CS216274B1 (en) | 1980-05-19 | 1980-05-19 | 15-+l2,3-epoxypropyl+p-7,15-diazadispiro+l5,1,5,3+p hexadekan-14,16-dion and method of making the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS345680A CS216274B1 (en) | 1980-05-19 | 1980-05-19 | 15-+l2,3-epoxypropyl+p-7,15-diazadispiro+l5,1,5,3+p hexadekan-14,16-dion and method of making the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS216274B1 true CS216274B1 (en) | 1982-10-29 |
Family
ID=5374677
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS345680A CS216274B1 (en) | 1980-05-19 | 1980-05-19 | 15-+l2,3-epoxypropyl+p-7,15-diazadispiro+l5,1,5,3+p hexadekan-14,16-dion and method of making the same |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS216274B1 (en) |
-
1980
- 1980-05-19 CS CS345680A patent/CS216274B1/en unknown
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