CS223420B1 - Light stabilizer with combined effect based on copolyether of sterically hindered piperazinedione and 2-hydroxybenzophenone and its preparation - Google Patents
Light stabilizer with combined effect based on copolyether of sterically hindered piperazinedione and 2-hydroxybenzophenone and its preparation Download PDFInfo
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- CS223420B1 CS223420B1 CS654781A CS654781A CS223420B1 CS 223420 B1 CS223420 B1 CS 223420B1 CS 654781 A CS654781 A CS 654781A CS 654781 A CS654781 A CS 654781A CS 223420 B1 CS223420 B1 CS 223420B1
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- hydroxybenzophenone
- light stabilizer
- piperazinedione
- sterically hindered
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Abstract
Vynález sa týká světelného stabilizátora s kombinovaným účinkom na báze kopolyéteru stéricky bráněného piperazíndiónu a 2-hydroxybenzofenónu a sposobu jeho přípravy. Podstata vynálezu spočívá v tom, že na 15- (2,3-epoxypropyl) -7,15-diazadispiro- -[5,l,5,3]hexadekán-14,16-dion sa působí 2- -hydroxy-4-(2,3-epoxypropoxy jbenzofenónom za katalýzy Lewisových báz pri zvýšenej tepiote v atmosféře dusíka. Vynález má použitie na přípravu světelného stabilizátora polymérov.The invention relates to a light stabilizer with a combined effect based on a copolyether of sterically hindered piperazinedione and 2-hydroxybenzophenone and a method of its preparation. The essence of the invention is that 15-(2,3-epoxypropyl)-7,15-diazadispiro-[5,1,5,3]hexadecane-14,16-dione is treated with 2-hydroxy-4-(2,3-epoxypropoxy)benzophenone under the catalysis of Lewis bases at elevated temperature in a nitrogen atmosphere. The invention is used for the preparation of a light stabilizer for polymers.
Description
223420 3
Vynález sa týká kopolymérneho světelnéhostabilizátora na báze stéricky bráněného pi-perazíndiónu a 2-hydroxybenzofenónu, u kto- 4
rého sa v hlavnom reťazci opakuje štruktúrna jednotka vzorca I
(I) & kde n má hodnotu 1 až 100 a ďalej sa vyná-lez týká spósobu přípravy tohto kopolyméru.
SpSsob přípravy uvedeného kopolymérne-ho stabilizátora je založený na kopolyadíciizlúčeniny vzorca II
HO
so zlúčeninou vzorca III
(III) v rozmedzí teplot 130 až 200 °C, pričom saako katalyzátory kopolyadície použijú Lewi-sove bázy, ako napr. terciárně aminy (tri-etylamín, tri-n-butylamín, tri-n-hexylamín,benzyldimetylamín, trilaurylamín), alebdkyslé katalyzátory, ako napr. fluorid boritýa jeho kopolyméry, chlorid cíničitý alebochlorid hlinitý.
Kopolymér podl'a predmetu vynálezu ob-sahuje dva odlišné substituenty naviazanéna polyéterový reťazec, pričom oba splňujúfunkciu štruktúrneho zoskupenia s fotosta-bilizačným účinkom. 2-Hydroxybenzofenóno-vé časti makromolekuly absorbujú škodlivéžiarenie v blízkej ultrafialovej oblasti slneč-ného žiarenia a piperazínové štruktúrnečlánky inhibujú radikálové procesy. Tietokopolyméry móžu mať využitie ako kombi-nované světelné stabilizátory benzofenón-pi-perazínového typu s eliminovanou prchavos-fou a zníženou extrahovateTnosťou pre zvý-šenie životnosti úžitkových polymérov alebo možu slúžiť na inhibíciu iných radikálovýchprocesov v dalších systémoch. Příklad 1
Do hrubostennej skúmavky sa vloží 0,9192gramu (0,003 mol) 15-(2,3-epoxypropyl )-7,15--diazadispiro [ 5,1,5,3 ] hexadekán-14,16-diónu,0,7629 g (0,003 mol) 2-hydroxy-4-(2,3-epoxy-propoxyjbenzofenónu a 5 mol. °/o trilauryl-amínu ako katalyzátore. Skúmavka sa naj-prv evakuuje, premyje suchým dusíkom, za-taví a umiestni do olejového kúpefa regulo-vaného na teplotu 190 °C na dobu 5 hod. Poskončení reakcie sa ampula ochladí a otvoríobsah sa rozpustí v acetóne a prezráža vo-dou. Získaný koloidný roztok sa vysolí schloridom sodným, přefiltruje a premyje ma-lým množstvom vody. Získá sa žltkastý práš-kovitý polymer vo vysokom výtažku s teplo-tou topenia v rozmedzí 92 až 97 °C a mole-kulovou hmotnosťou 1680 (stanovené termo-osmometricky).
Elementárna analýza pre C33H40N2O7
Vypočítané: N = 4,86 % Nájdená: N = 4,77 % IČ spektrum (chloroform):
Umax = 850, 930, 950, 980, 1050, 1090, 1135,1200, 1290, 1330, 1440, 1460, 1520,1610, 1670, 1720, 2960, 3420 cm"1 Příklad 2
Postupovalo sa ako v příklade 1 s týmrozdielom, že sa reakcia uskutečňovala 5hod. při teplote 190 °C, ako katalyzátor sapoužil dietyléter-trifluorboran v množstve 5mol. %. Získal sa žltkastý práškoviťý poly-mér s priemernou číselnou molekulovouhmotnosťou 1720 (stanovené osmometriou vparnéj fáze).
Elementárna analýza pre C33H40N2O7
Vypočítané: N = 4,86 % Nájdené: N = 4,81 %.
223420 3
The present invention relates to a copolymer lightweight stabilizer based on sterically hindered piperazinedione and 2-hydroxybenzophenone.
In the main chain, the structural unit of Formula I is repeated
(I) & wherein n is 1 to 100, and the invention further relates to a process for preparing the copolymer.
The process for preparing said copolymer stabilizer is based on the copolyaddic compounds of formula II
HIM
with a compound of formula III
(III) in a temperature range of 130 to 200 ° C, using the Lewis bases such as tertiary amines (triethylamine, tri-n-butylamine, tri-n-hexylamine, benzyldimethylamine, trilaurylamine) as copolyadienation catalysts, catalysts such as boron trifluoride and copolymers thereof, stannic chloride or aluminum chloride.
The copolymer of the present invention comprises two different polyether-linked substituents, both of which function as a structural moiety with photostability. The 2-hydroxybenzophenone moieties of the macromolecule absorb harmful radiation in the near ultraviolet region of the sun and the piperazine structural cells inhibit radical processes. The triopolymers can be used as combined light stabilizers of benzophenone-piperazine type with eliminated volatility and reduced extractability to increase the useful life of useful polymers, or they can serve to inhibit other radical processes in other systems. Example 1
0.9192gram (0.003 mol) of 15- (2,3-epoxypropyl) -7,15-diazadispiro [5,1,5,3] hexadecane-14,16-dione, 0.7629 g (0.7629 g) is placed in a thick-walled tube. 0.003 mol) of 2-hydroxy-4- (2,3-epoxy-propoxybenzophenone and 5 mol% of trilauryl amine catalyst) The tube is first evacuated, washed with dry nitrogen, sealed and placed in an oil bath regulo The reaction was stopped at 190 ° C for 5 hours. After completion of the reaction, the vial was cooled and the contents were dissolved in acetone and precipitated with water, and the colloidal solution obtained was salted with sodium chloride, filtered and washed with a small amount of water to give a yellowish powder. a high-yield, high-melting polymer with a melting point of 92-97 ° C and a molecular weight of 1680 (determined thermo-osmometrically).
Elemental analysis for C 33 H 40 N 2 O 7
Calculated: N = 4.86% Found: N = 4.77% IR spectrum (chloroform):
Max = 850, 930, 950, 980, 1050, 1090, 1135, 1200, 1290, 1330, 1440, 1460, 1520, 1610, 1670, 1720, 2960, 3420 cm -1.
The procedure was as in Example 1, with the difference that the reaction was carried out for 5 hours. at 190 ° C, 5mol diethyl ether-trifluoroborane was used as the catalyst. %. A yellowish powdered polymer with an average molecular weight of 1720 (determined by the osmometry of the vapor phase) was obtained.
Elemental analysis for C 33 H 40 N 2 O 7
N = 4.86%. Found: N = 4.81%.
Claims (3)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS654781A CS223420B1 (en) | 1981-09-04 | 1981-09-04 | Light stabilizer with combined effect based on copolyether of sterically hindered piperazinedione and 2-hydroxybenzophenone and its preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS654781A CS223420B1 (en) | 1981-09-04 | 1981-09-04 | Light stabilizer with combined effect based on copolyether of sterically hindered piperazinedione and 2-hydroxybenzophenone and its preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS223420B1 true CS223420B1 (en) | 1983-10-28 |
Family
ID=5412791
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS654781A CS223420B1 (en) | 1981-09-04 | 1981-09-04 | Light stabilizer with combined effect based on copolyether of sterically hindered piperazinedione and 2-hydroxybenzophenone and its preparation |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS223420B1 (en) |
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1981
- 1981-09-04 CS CS654781A patent/CS223420B1/en unknown
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