CS216275B1 - 2- (7,15-Diazadispiro [5,1,5,3] hexadecan-14,16-dione-15-yl) propanedioic acid dialkyl esters and process for their preparation - Google Patents
2- (7,15-Diazadispiro [5,1,5,3] hexadecan-14,16-dione-15-yl) propanedioic acid dialkyl esters and process for their preparation Download PDFInfo
- Publication number
- CS216275B1 CS216275B1 CS345780A CS345780A CS216275B1 CS 216275 B1 CS216275 B1 CS 216275B1 CS 345780 A CS345780 A CS 345780A CS 345780 A CS345780 A CS 345780A CS 216275 B1 CS216275 B1 CS 216275B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- dione
- diazadispiro
- hexadecan
- preparation
- propanedioic acid
- Prior art date
Links
- -1 hexadecan-14,16-dione-15-yl Chemical group 0.000 title claims description 6
- 150000002148 esters Chemical class 0.000 title claims description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 title claims description 3
- HCPOCMMGKBZWSJ-UHFFFAOYSA-N ethyl 3-hydrazinyl-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)NN HCPOCMMGKBZWSJ-UHFFFAOYSA-N 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title description 4
- 238000000034 method Methods 0.000 title description 2
- 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 3
- FNJVDWXUKLTFFL-UHFFFAOYSA-N diethyl 2-bromopropanedioate Chemical compound CCOC(=O)C(Br)C(=O)OCC FNJVDWXUKLTFFL-UHFFFAOYSA-N 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 238000004519 manufacturing process Methods 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 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
- 229920000642 polymer Polymers 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- FEXBEKLLSUWSIM-UHFFFAOYSA-N 2-Butyl-4-methylphenol Chemical compound CCCCC1=CC(C)=CC=C1O FEXBEKLLSUWSIM-UHFFFAOYSA-N 0.000 description 1
- VBZOUUJVGADJBK-UHFFFAOYSA-N 2-bromopropanedioic acid Chemical compound OC(=O)C(Br)C(O)=O VBZOUUJVGADJBK-UHFFFAOYSA-N 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-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
- 150000001875 compounds Chemical class 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
- 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
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 238000012667 polymer degradation Methods 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
- 150000003384 small molecules Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 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
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Description
Vynález sa týká dialkylesterov kyseliny 2-(7,15-diazadispiro [5,1,5,3] hexadekán-14,16-dión-15-yl) propándiovej nasledujúceho vzorca:The invention relates to dialkyl esters of 2- (7,15-diazadispiro [5,1,5,3] hexadecan-14,16-dione-15-yl) propanedioic acid of the following formula:
OROR
a spósobu ich přípravy; pričom R značí metylová alebo etylovú skupinu.and a process for their preparation; wherein R is methyl or ethyl.
Sposob přípravy týchto zlúčenín, ktoré nie sú známe z literatury, je založený na reakcii dialkylesteru kyseliny 2-brómpropándiovej s 7,15-diazadispiro [5,1,5,3] hexadekán-14,16-diónom.The preparation of these compounds, which are not known from the literature, is based on the reaction of 2-bromopropanedioic acid dialkyl ester with 7,15-diazadispiro [5,1,5,3] hexadecane-14,16-dione.
Wtó ^tarny pafriass do skupiny stéricky bráněných amínov móžu samy o sebe plnit funkciu světelného stabilizátora. Nevýhodou nízkomolekulových látok tejto skupiny je ich čiastočná vypieratelnosť z užitkových polymérov. Příprava polymérnych světelných stabilizátorov tento nedostatok odstraňuje. K tomuto účelu móžu slúžiť látky, ktoré sú predmetom vynálezu.Thus, the pafriass group into the group of sterically hindered amines can themselves act as a light stabilizer. A disadvantage of the low molecular weight compounds of this group is their partial washability from utility polymers. The preparation of polymeric light stabilizers eliminates this drawback. The substances which are the subject of the invention can be used for this purpose.
Příklad 1Example 1
K 5,76 g (0,02 mólu) draselnej soli 7,15-diazadispiro [5,1,5,3] hexadekán — 14,16-diónu v 60 ml bezvodého dimetylformamidu sa za stálého miešanía pri teplote okolo 80 °C prikvapkáva v priebehu 1/2 až 1 hodiny roztokTo 5.76 g (0.02 mole) of the potassium salt of 7,15-diazadispiro [5,1,5,3] hexadecane-14,16-dione in 60 ml of anhydrous dimethylformamide is added dropwise with stirring at a temperature of about 80 ° C. within 1/2 to 1 hour of solution
4,78 g (0,02 mólu) dietylesteru kyseliny 2brómpropándiovej v 20 ml bezvodého dimetylformamidu. Zmes sa ďalej zahrieva a mieša po dobu 3 hodin a nechá sa ochladit. Vyextrahuje sa třikrát éterom a spojené éterické extrakty sa dokladné premyjú vodou, vysušia bezvodým síranem sodným a éter sa odpaří. Získaný zvyšok sa prekryštalizuje a etanolu. Získá sa produkt v podobě bielej kryštalickej látky s t.t. = 82 až 85 °C.4.78 g (0.02 mol) of 2-bromopropanedioic acid diethyl ester in 20 ml of anhydrous 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 washed thoroughly with water, dried over anhydrous sodium sulphate and the ether is evaporated. The residue is recrystallized from ethanol. Obtained as a white crystalline solid, m.p. M.p. = 82-85 ° C.
Elementárna analýza pre C2tH32N2O6: Vypočítané:H, C 2 t H 32 N 2 O 6: Calculated:
C = 61,75 %; H = 7,90 %; N = 6,85 % Nájdené:C = 61.75%; H = 7.90%; N = 6.85% Found:
C = 62,04 %; H = 7,91 %; N = 6,59 % iC spektrum (CHCI3):C = 62.04%; H = 7.91%; N = 6.59% iC spectrum (CHCl 3):
Umax = 860, 975, 1030, 1090, 1190, 1260, 1295, 1345, 1365, 1445, 1680, 1725, 1750, 2940Umax = 860, 975, 1030, 1090, 1190, 1260, 1295, 1345, 1365, 1445, 1680, 1725, 1750, 2940
Příklad 2Example 2
100 hmotnostných dielov nestabilizovaného 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. dielmi zlúčeniny, pripravenej podía příkladu 1. Po odpaření rozpúštadla 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 predohnievali 1 minútu pri teplote 190 QC. 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 .mu.-di-tert. butyl-4-methylphenol, 0.15 wt. % of calcium stearate and 0.2 wt. After evaporation of the solvent, 0.2 mm thick films were pressed from the mixture at 20 MPa at 190 ° C for 30 seconds. Just prior to pressing, the samples still predohnievali 1 minute at 190 Q C films were irradiated mercury lamp with a power of 125 W at a distance of 7 cm from the source and that a filter is used
1,6 hmot. % roztok síranu meďnatého. Degradácia polyméru sa sledovala vývoj om hydroperoxidového a karbonylového pásu v infračervených spektrách. Kým doba dosiahnutia 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 polymer degradation was followed by the development of the γ hydroperoxide 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 |
|---|---|---|---|
| CS345780A CS216275B1 (en) | 1980-05-19 | 1980-05-19 | 2- (7,15-Diazadispiro [5,1,5,3] hexadecan-14,16-dione-15-yl) propanedioic acid dialkyl esters and process for their preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS345780A CS216275B1 (en) | 1980-05-19 | 1980-05-19 | 2- (7,15-Diazadispiro [5,1,5,3] hexadecan-14,16-dione-15-yl) propanedioic acid dialkyl esters and process for their preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS216275B1 true CS216275B1 (en) | 1982-10-29 |
Family
ID=5374687
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS345780A CS216275B1 (en) | 1980-05-19 | 1980-05-19 | 2- (7,15-Diazadispiro [5,1,5,3] hexadecan-14,16-dione-15-yl) propanedioic acid dialkyl esters and process for their preparation |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS216275B1 (en) |
-
1980
- 1980-05-19 CS CS345780A patent/CS216275B1/en unknown
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