CS216272B1 - 15-alyl-7,15diazadispiro+1,5,3+p hexadekan-14,16-dion and method of making the same - Google Patents
15-alyl-7,15diazadispiro+1,5,3+p hexadekan-14,16-dion and method of making the same Download PDFInfo
- Publication number
- CS216272B1 CS216272B1 CS345480A CS345480A CS216272B1 CS 216272 B1 CS216272 B1 CS 216272B1 CS 345480 A CS345480 A CS 345480A CS 345480 A CS345480 A CS 345480A CS 216272 B1 CS216272 B1 CS 216272B1
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- CS
- Czechoslovakia
- Prior art keywords
- hexadekan
- alyl
- dion
- making
- same
- Prior art date
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- 238000004519 manufacturing process Methods 0.000 title description 2
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims 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 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 159000000000 sodium salts Chemical class 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
- 229920000642 polymer Polymers 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-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
- 150000001875 compounds Chemical class 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
- NWRYOVCYBJWBEC-UHFFFAOYSA-N 3-oxohexadecanal Chemical compound CCCCCCCCCCCCCC(=O)CC=O NWRYOVCYBJWBEC-UHFFFAOYSA-N 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
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 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
- 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
- 238000006731 degradation reaction Methods 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
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 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
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 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-alyl-7,l 5-diazadispiro [5,1,5,3]-hexaidekán-l4,16-diónu nasledujúceho vzorca:The invention relates to 15-allyl-7,15-diazadispiro [5,1,5,3] -hexaidecane-14,16-dione of the following formula:
‘ a jeho sposobu přípravy.Jeho and its method of preparation.
SpÓsob pripravy zlúčeniny, 'ktorá nie je známou z literatúry, je založený na reakoii alylbromidu s 7,15-diazadispiro [5,1,5,3] hexadekán-14,16-diónom.A process for preparing a compound not known in the literature is based on the reaction of allyl bromide with 7,15-diazadispiro [5,1,5,3] hexadecane-14,16-dione.
Uvedenú zlúčeninu možno zařadit do skupiny stéricky bráněných světelných staibilizátorov. Nevýhodou nízkomolekulových lá tok tejto skupiny je ich čiastočná vypieratelnosť z úžitkových polymérov. Příprava polymérneho světelného stabilizátora tieto nedostatky odstraňuje. K íomuto účelu moze slúžiť látka, ktorá je predmetom vynálezu.Said compound may be classified as a class of sterically hindered light stabilizers. A disadvantage of the low molecular weight latex of this group is their partial washability from utility polymers. The preparation of a polymeric light stabilizer removes these drawbacks. The substance of the invention may serve for this purpose.
1627216272
Příklad 1Example 1
K 2,88 g (0,01 molu) draselnej soli 7,15-diazodispiro , [5,1,5,3] hexadekán-14,16-diónu v 30 ml bezv. dimetylformamidu a za stálého miešania pri teplote okolo 70 °C prikvapkáva v priebehu 1/2 až 1 hodiny roztok 1,21 g (0,01 m) alylbromidu v 15 ml bezv. dimetylformamidu. Zmes sa ďalej zahrieva a mieša po dobu 3 hodin a nechá sa ochladit. Vyextrahuje sa trikrát éterom a spojené éterické extrakty sa dokladné premyjú vodou, vysušia bezv. Na2SO4 éter sa odpaří. Získaný zvyšok sa prekryštalizuje z etanolu. Získá sa produkt v poďobe bielej kryštalickej látky s t.t. = = 57-60 °C.To 2.88 g (0.01 mol) of the potassium salt of 7,15-diazodispiro, [5,1,5,3] hexadecane-14,16-dione in 30 ml of anhydrous salt. of dimethylformamide and stirring at a temperature of about 70 ° C, a solution of 1.21 g (0.01 m) of allyl bromide in 15 ml of aq. dimethylformamide. 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. Evaporate to 2 SO4 ether. The residue is recrystallized from ethanol. The product is obtained in the form of a white crystalline solid, mp = 57-60 ° C.
Elementáma analýza pre CtyHgfiNaCL: Vypočítané:Elemental analysis for CtyHgfiNaCL: Calculated:
C = 70,31 %; H = 9,02 %; N = 9,65 %. Nájdené:C = 70.31%; H = 9.02%; N = 9.65%. found:
C = 69,99 %; H = 9,08 %; N = 9,53 %.C = 69.99%; H = 9.08%; N = 9.53%.
IČ spektrum (CHCI3):IR (CHCl3):
w = 930, 980, 1075, 1140, 1200, 1265, 1340, 1450, 1670, 1720, 3940.w = 930, 980, 1075, 1140, 1200, 1265, 1340, 1450, 1670, 1720, 3940 < tb >
iand
Příklad 2Example 2
100 hmotnostných dielov nestabilizovaného práškovitého polypropylénu sa impregnovalo v dichlórmetáne s 0,1 hmot. dielmi 2,6-di-terc. butyl-4-metyl-fenolu, 0,15 hmot. dielmi stearanu vápenatého a s 0,2 hmot. dielmi zlúčeniny, pripravenej podl’a příkladu 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 minutu pri teplote 190 °C. Fólie sa ozařovali ortuťovou výbojkou o výkone 125 W vo vzdialenosti 7 cm od zdroja a ako filter sa použil100 parts by weight of unstabilized 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. After evaporation of the solvent, 0.2 mm thick sheets were pressed from the mixture at 20 MPa at 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 filter was used
1,6 hmot. % roztok síranu meďnatého. Degradácia polyméru sa sledovala vývojom hydroperoxidového a karbonylového pásu v infračervených spektrách. Kým doba dosiáhnutia karbonylového indexu 0,2 u čistého polypropylénu bola 480 hodin, stabilizovaný polymér nedosiahol túto hodnotu ani za 3000 'hodin.1.6 wt. % copper sulfate solution. The degradation of the polymer was monitored by the development of the hydroperoxide and carbonyl bands in the infrared spectra. While the carbonyl index reached 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 |
|---|---|---|---|
| CS345480A CS216272B1 (en) | 1980-05-19 | 1980-05-19 | 15-alyl-7,15diazadispiro+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 |
|---|---|---|---|
| CS345480A CS216272B1 (en) | 1980-05-19 | 1980-05-19 | 15-alyl-7,15diazadispiro+1,5,3+p hexadekan-14,16-dion and method of making the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS216272B1 true CS216272B1 (en) | 1982-10-29 |
Family
ID=5374651
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS345480A CS216272B1 (en) | 1980-05-19 | 1980-05-19 | 15-alyl-7,15diazadispiro+1,5,3+p hexadekan-14,16-dion and method of making the same |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS216272B1 (en) |
-
1980
- 1980-05-19 CS CS345480A patent/CS216272B1/en unknown
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