CS206541B1 - 15-methacroyl-7,15-diaazadispiro/5,1,5,3/-hexadecane and its preparation method - Google Patents
15-methacroyl-7,15-diaazadispiro/5,1,5,3/-hexadecane and its preparation method Download PDFInfo
- Publication number
- CS206541B1 CS206541B1 CS24480A CS24480A CS206541B1 CS 206541 B1 CS206541 B1 CS 206541B1 CS 24480 A CS24480 A CS 24480A CS 24480 A CS24480 A CS 24480A CS 206541 B1 CS206541 B1 CS 206541B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- hexadecane
- preparation
- methacroyl
- diaazadispiro
- diazadispiro
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 5
- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 4
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical class [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
Description
(54) Ib-metakroyl-T.IS-diazadispiro [5,1,5,31 hexadekán a spósob jeho přípravy i(54) Ib-methacroyl-T.IS-diazadispiro [5,1,5,31 hexadecane and process for its preparation i
Vynález sa týká zlúčeniny 15-metakroyl-7,15-diazadispi.ro£ 5,1,5,33hexadekánu vzorca IThe present invention relates to 15-methacroyl-7,15-diazadispiro [eta] < 5,1,5,33 > hexadecane of formula I
Q_s i’* 1 Q_ s i ' * 1
Η-Ν·< ; N-CO-C = CH~ /1/, a spósobu jeho přípravy.Η-Ν · <; N-CO-C = CH- (1), and a process for its preparation.
Spósob přípravy zlúčeniny vzorca i, ktorá nie je.známa z literatury, je založený na reakcii chloridu kyseliny metakrylovej s 7, 15-diazadispiro£ 5 , 1,5,3 Jhexadekánom.A process for the preparation of a compound of formula (i) which is not known from the literature is based on the reaction of methacrylic acid chloride with 7,15-diazadispiro [delta], 1,5,3] hexadecane.
Stérícky bráněné aminy sú modernou triedou světelných stabílizátorov plastických látok. Nevýhodou nízkomolekulových látok tejto triedy je ich lahká vypieratelnosť a toxicita. Uvedené nedostatky riesi zabudovanie stabilízátora do polymeru, ktorý má byť stabilizovaný, alebo použitie polymérneho stabilízátora. K týmto úČelom slúži látka, ktorá je predmetom vynálezu.The hindered amines are a modern class of plastic light stabilizers. The disadvantage of low-molecular-weight substances of this class is their easy washability and toxicity. These drawbacks are solved by incorporating a stabilizer into the polymer to be stabilized or by using a polymeric stabilizer. The substance of the invention serves for this purpose.
PříkladExample
Do roztoku 10 g /0,045 mol/ 7, 15-diazadíspiro£ 5, 1 ,5,3 3hexadekánu a 5,6 g /0,055 mol/ tríetylamínu v 150 ml sušeného benzénu sa přidávalo pri teplote 5 až 10 °C 5,6 g /0,052 mol/ chloridu kyseliny metakrylovej. Zmes sa potom miešala 24 hodin pri teplote miestnosti. Reakčná zmes sa přefiltrovala a pevná časť sa rozpustila v nasýtenom roztoku uhličitanu draselného a vyextrahovala chloroformom. Organické vrstvy sa spojili a vákuovo zahustili. Surový produkt sa přefiltroval cez 4 cm vrstvu sílíkagélu, rozpustil v n-hexáne a nechal kryštalizovať. Získala sa biela kryštalická látka s t. t. 75 až 77 °C v 69 Z výtažku.To a solution of 10 g (0.045 mol) 7,15-diazadispiro (5,1,5,3,3-hexadecane) and 5.6 g (0.055 mol) triethylamine in 150 ml dried benzene was added 5.6 g at 5-10 ° C. (0.052 mol) methacrylic acid chloride. The mixture was then stirred at room temperature for 24 hours. The reaction mixture was filtered and the solid was dissolved in saturated potassium carbonate solution and extracted with chloroform. The organic layers were combined and concentrated in vacuo. The crude product was filtered through a 4 cm layer of silica gel, dissolved in n-hexane and allowed to crystallize. A white crystalline substance with m.p. t. 75-77 ° C in 69 of the extract.
’η-NHR. /CDC13/ J = 1,1 /s-1H > N-H/; 1,4/m-20H X2>/; 1,88 /t-3K CH3/s 3,3/s-4H CH2-N-CH2/; 4,92 a 5,1 /2m-2H =CH2/.'Η-NHR. (CDCl3 ) (J = 1.1 (s-1H) NH); 1.4 (m-20H X 2); 1.88 (t-3K CH 3 / s 3.3 (s-4H CH 2 -N-CH 2) ); 4.92 and 5.1 (2m-2H = CH2 ) .
IC /CHClj/ Pmax 720, 1099, 1200, 1310, 1450, 1620, 1650, 2940, 3400.IC / CHCl 3 / P max 720, 1099, 1200, 1310, 1450, 1620, 1650, 2940, 3400.
Hmotnostné spektrum m/e = 290/M+/, 248, 221 , 178, 82, 69.Mass Spectrum m / e = 290 (M < + >), 248, 221, 178, 82, 69.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS24480A CS206541B1 (en) | 1980-01-11 | 1980-01-11 | 15-methacroyl-7,15-diaazadispiro/5,1,5,3/-hexadecane and its preparation method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS24480A CS206541B1 (en) | 1980-01-11 | 1980-01-11 | 15-methacroyl-7,15-diaazadispiro/5,1,5,3/-hexadecane and its preparation method |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS206541B1 true CS206541B1 (en) | 1981-06-30 |
Family
ID=5334215
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS24480A CS206541B1 (en) | 1980-01-11 | 1980-01-11 | 15-methacroyl-7,15-diaazadispiro/5,1,5,3/-hexadecane and its preparation method |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS206541B1 (en) |
-
1980
- 1980-01-11 CS CS24480A patent/CS206541B1/en unknown
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