CS223421B1 - Polyester light stabilizer based on sterically hindered piperazinedione and phthalic acid and its preparation - Google Patents
Polyester light stabilizer based on sterically hindered piperazinedione and phthalic acid and its preparation Download PDFInfo
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- CS223421B1 CS223421B1 CS654981A CS654981A CS223421B1 CS 223421 B1 CS223421 B1 CS 223421B1 CS 654981 A CS654981 A CS 654981A CS 654981 A CS654981 A CS 654981A CS 223421 B1 CS223421 B1 CS 223421B1
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- piperazinedione
- light stabilizer
- sterically hindered
- phthalic acid
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Abstract
Vynález sa týká polyesterového světelného stabilizátora na báze stéricky bráněného piperazíndiónu a kyseliny ftalovej a sposobu jeho přípravy. r Podstata vynálezu spočívá v tom, že na 2,3-epoxypropyl derivát tetrasubstituovaného piperazíndiónu sa pósobí pri zvýšenej i teplote ftalanhydridu v přítomnosti bázických katalyzátorov. Zlúčenina so štruktúrnymi článkami stéricky bráněného derivátu piperazínu má využitie ako světelný stabilizátor róznych úžitkových polymérov.The invention relates to a polyester light stabilizer based on sterically hindered piperazinedione and phthalic acid and a method of its preparation. r The essence of the invention consists in the fact that phthalic anhydride acts on the 2,3-epoxypropyl derivative of tetrasubstituted piperazinedione at an elevated temperature in the presence of basic catalysts. The compound with the structural elements of a sterically hindered piperazine derivative is used as a light stabilizer of various useful polymers.
Description
223421 3 4
Vynález sa týká polymérneho světelnéhostabilizátora piperazínového typu, ktorý za-
hrnuje v hlavnom reťazci nasledujúcu štruk-túrnu jednotku vzorce I
kde n je celé číslo v rozmedzí 1 až 100 asposobu jeho přípravy.
Sposob přípravy uvedeného polymérnéhosvetelnéhoi stabilizátora spočívá v tom, že sana zlúčeninu vzorca II
pósobí ftalanhydridom pri teplote 130 °C až200 °C. Reakcia sa prevádza v přítomnostiterciárnych amínov ako katalyzátorov reak-cie, například trietylamínu, tri-n-hexylamí-nu, trilaurylamínu.
Zlúčeniny so štruktúrnymi článkami stéric-ky bráněných derivátov piperazínu pósobiaako světelné stabilizátory róznych úžitko-vých polymérov. Nevýhodou nízkomolekulo-vých látok na báze stéricky bráněných amí-nov je ich značná prchavosť a vypieratel'-nosť z výrobkov s velkým povrchom, ako súfólie a vlákna. Vzhladom na extrahovatel'-nosť a prchavosť je potřebné brať do úvahytoxicitu týchto nízkomolekulárnych látok,čo obmedzuje možnosti ich aplikácie. Rieše-nie týchto problémov poskytuje využitie po-lymérnych stabilizátorov připravených po-dlá predmetu tohto vynálezu. Příklad 1
Do hrubostennej skúmavky sa vložilo 0,9192 g (0,003 molu) 15-(2,3-epoxyprúpyl)--7,15-diazadispiroi[ 5,1,5,3 ]hexadekán-14,16--diónu, 0,4444g (0,003 molu) ftalanhydridua 5 mol. % trilaurylamínu ako katalyzáto-re. Skúmavka sa evakuovala, premyla su-chým dusíkom a zatavila. Potom sa umiest-nila do olejového kúpela regulovaného nateplotu 190 °C po dobu 5 hod. Po ukončeníreakcie sa ampula ochladila a rozbila. Ob-sah sa rozpustil v acetone, prezrážal vodoua získaný koloidný roztok sa vysolil s chlo-ridom sodným-. Vzniknutá zrazenina poly-esteru sa odfiltrovala, premyla malým množ-stvom vody a dokonale vysušila za vysoké-ho vákua pri teplote 60 °C. Izoloval sa žlt-kastý, sklovitý, 1'ahko spráškovatefný poly-mer s teplotou topenia v rozmedzí 92 až 98°Celsia a molekulovou hmotnosťou 2647 (sta-novená termoosmometricky).
Elementárna analýza pre C25H30N2O6.
Vypočítané: 6,63 % N. Nájdené: 6,51 % N. 7 IČ spektrum (chloroform):
Vmax = 910, 965, 1020, 1035, 1070, 1130, * 1170, 1195, 1265, 1285, 1330, 1450, 1670, 1720, 2940, 3500 cm-1. Příklad 2
Postupovalo sa ako v příklade 1, s týmrozdielom, že reakcia sa prevádzala pri tep-lote 150 °C po dobu 10 hod. v přítomnosti5 mol. % tri-n-hexylamínu. Produkt sa izolo-val postupom ako v příklade 1, pričom sazískal polymér s molekulovou hmotnosťou2530. Elementárnou analýzou sa zistil obsahdusíka 6,55 %.
223421 3 4
The invention relates to a polymeric light stabilizer of the piperazine type, which
in the main chain the following structural unit of formula I
wherein n is an integer ranging from 1 to 100 and for its preparation.
The process for preparing said polymer-light stabilizer is that the sana compound of formula II
with phthalic anhydride at 130 ° C to 200 ° C. The reaction is carried out in the presence of titanium amines as reaction catalysts, for example triethylamine, tri-n-hexylamine, trilaurylamine.
The compounds with structural elements of sterically hindered piperazine derivatives are used as light stabilizers for various useful polymers. A disadvantage of low molecular weight sterile hindered amines is their considerable volatility and washability from large surface products such as foils and fibers. Due to the extractability and volatility it is necessary to take into account the toxicity of these low molecular weight substances, which limits the possibilities of their application. The solution of these problems is provided by the use of polymeric stabilizers prepared according to the present invention. Example 1
0.9192 g (0.003 mol) of 15- (2,3-epoxypropyl) -7,15-diazadispiro [5,1,5,3] hexadecane-14,16-dione, 0.4444g was charged into a thick-walled tube. (0.003 mol) phthalic anhydride 5 mol. % trilaurylamine catalyst. The tube was evacuated, washed with dry nitrogen and sealed. It was then placed in an oil bath of controlled temperature of 190 ° C for 5 hours. After completion of the reaction, the ampoule was cooled and broken. The content was dissolved in acetone, precipitated with water, and the obtained colloidal solution was salted out with sodium chloride. The resulting poly-ester precipitate was filtered off, washed with a small amount of water and dried thoroughly under high vacuum at 60 ° C. A yellowish, glassy, readily dustable polymer was isolated with a melting point of 92-98 ° C and a molecular weight of 2647 (determined thermo-isometric).
Elemental analysis for C 25 H 30 N 2 O 6.
N, 6.61. Found: N, 6.51. 7 IR spectrum (chloroform):
Ν max = 910, 965, 1020, 1035, 1070, 1130, * 1170, 1195, 1265, 1285, 1330, 1450, 1670, 1720, 2940, 3500 cm -1. Example 2
The procedure was as in Example 1, except that the reaction was carried out at 150 ° C for 10 hours in the presence of 5 moles. % tri-n-hexylamine. The product was isolated as in Example 1 to yield a 2530 molecular weight polymer. Elemental analysis showed a nitrogen content of 6.55%.
Claims (3)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS654981A CS223421B1 (en) | 1981-09-04 | 1981-09-04 | Polyester light stabilizer based on sterically hindered piperazinedione and phthalic acid and its preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS654981A CS223421B1 (en) | 1981-09-04 | 1981-09-04 | Polyester light stabilizer based on sterically hindered piperazinedione and phthalic acid and its preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS223421B1 true CS223421B1 (en) | 1983-10-28 |
Family
ID=5412809
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS654981A CS223421B1 (en) | 1981-09-04 | 1981-09-04 | Polyester light stabilizer based on sterically hindered piperazinedione and phthalic acid and its preparation |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS223421B1 (en) |
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1981
- 1981-09-04 CS CS654981A patent/CS223421B1/en unknown
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