CS252976B1 - Poly(ethylene-2,3-bis/1,2,2,6,6-pentamethyl-4-piperidyloxy/butandionate)and method of its production - Google Patents
Poly(ethylene-2,3-bis/1,2,2,6,6-pentamethyl-4-piperidyloxy/butandionate)and method of its production Download PDFInfo
- Publication number
- CS252976B1 CS252976B1 CS859498A CS949885A CS252976B1 CS 252976 B1 CS252976 B1 CS 252976B1 CS 859498 A CS859498 A CS 859498A CS 949885 A CS949885 A CS 949885A CS 252976 B1 CS252976 B1 CS 252976B1
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- CS
- Czechoslovakia
- Prior art keywords
- bis
- piperidyloxy
- pentamethyl
- ethylene
- poly
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 6
- 239000003054 catalyst Substances 0.000 claims description 5
- -1 1,2,2,6,6-pentamethyl-4-piperidyloxy Chemical group 0.000 claims description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 3
- HKJYVRJHDIPMQB-UHFFFAOYSA-N propan-1-olate;titanium(4+) Chemical compound CCCO[Ti](OCCC)(OCCC)OCCC HKJYVRJHDIPMQB-UHFFFAOYSA-N 0.000 claims description 3
- 239000008096 xylene Substances 0.000 claims description 3
- JNRAZIVKAWFQSZ-UHFFFAOYSA-N CN1C(CC(CC1(C)C)OC(C(=O)O)C(C(=O)O)OC1CC(N(C(C1)(C)C)C)(C)C)(C)C Chemical compound CN1C(CC(CC1(C)C)OC(C(=O)O)C(C(=O)O)OC1CC(N(C(C1)(C)C)C)(C)C)(C)C JNRAZIVKAWFQSZ-UHFFFAOYSA-N 0.000 claims description 2
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N sodium methoxide Substances [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- DKMROQRQHGEIOW-UHFFFAOYSA-N Diethyl succinate Chemical compound CCOC(=O)CCC(=O)OCC DKMROQRQHGEIOW-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000005108 dry cleaning Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 238000005201 scrubbing Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
Description
(54) Póly[ etylén-2,3-bis (l,2,2,6,6-pentainetyl-4-piperidyloxy)butándionát] a sposob jeho přípravy(54) Poles [ethylene-2,3-bis (1,2,2,6,6-pentainethyl-4-piperidyloxy) butanedionate] and process for its preparation
Vynález sa týká poly[etylén-2,3-bis(l,2,2,6,6-pentametyl-4-piperidyloxy) butándionátu] a sposobu jeho přípravy.The invention relates to poly [ethylene-2,3-bis (1,2,2,6,6-pentamethyl-4-piperidyloxy) butanedionate] and a process for its preparation.
Stéricky bráněné aminy sú velmi účinné světelné stabilizátory polymérov. Okrem vysoké] účinnosti sú na tieto stabilizátory kladené požiadavky nízkej toxicity a malej vypieratelnosti a prchavosti, aby sa obmedzil ich postupný úbytok z úžitkového polyméru už pri samotnom spracovaní, alebo neskór pri skladovaní, chemickom čistění alebo praní.Sterically hindered amines are very effective light stabilizers of polymers. In addition to their high efficiency, these stabilizers are subject to low toxicity and low scrubbing and volatility properties to reduce their gradual loss from the useful polymer during processing, or late storage, dry-cleaning or washing.
Riešenie týchto problémov poskytuje využitie stabilizátorov s vyššou molekulovou hmotnosťou. Podstatou tohto vynálezu je poly[etylén-2,3-bis(l,2,2,6,6-pentametyl-4-piperidyloxyj butándionát] vzorca IThe use of higher molecular weight stabilizers provides a solution to these problems. The present invention provides a poly [ethylene-2,3-bis (1,2,2,6,6-pentamethyl-4-piperidyloxy) butanedionate] of the formula I
h3ch 3 c
H-fH-F
1/CH31 / CH 3
I CHZ ch3 (2.I CH Z ch 3 (2.
kde n je 2 až 100. Podstatou vynálezu je ďalej sposob přípravy zlúčeniny vzorca I, ktorý sa vyznačuje tým, že sa na dialkylester kyseliny 2,3-bis (l,2,2,6,6-pentametyl-4-piperidyloxyjbutándiovej vzorca IIwherein n is from 2 to 100. The present invention further provides a process for the preparation of a compound of formula I which is characterized in that 2,3-bis (1,2,2,6,6-pentamethyl-4-piperidyloxy) butanedioic acid dialkyl ester of formula II
kde R je metylová alebo etylová skupina, posobí 1,2-etándiolom v suchom xylene pri teplote v rozmedzí od 100 až 160 °C v přítomnosti bázického katalyzátora — metanolátu sodného, lítiumamidu, tetrapropyltitanátu alebo tetrabutyltitanátu.wherein R is a methyl or ethyl group, it is treated with 1,2-ethanediol in dry xylene at a temperature ranging from 100 to 160 ° C in the presence of a basic catalyst - sodium methoxide, lithium amide, tetrapropyltitanate or tetrabutyl titanate.
Výhodou uvedeného vynálezu je zvačšenie molekulovej hmotnosti stabilizátora, čo vedie k eliminovaniu prchavosti a zníženiu jeho extrahovatelnosti z úžitkového polyméru·.An advantage of the present invention is to increase the molecular weight of the stabilizer, which results in elimination of volatility and a reduction in its extractability from the useful polymer.
Příklad 1Example 1
K reakčnej zmesi pozostávajúcej z 0,979 g (0,002 molu) dimetylesteru kyseliny 2,3-bis(l,2,2,6,6-pentametyl-4-piperidyloxyjbutándiovej II a 0,25 g (0,004 molu) 1,2-etándiolu v 10 ml suchého xylénu zahriatej na 110 °C sa přidá 0,05 g tetrapropyltitanátu ako katalyzátora. Zmes sa zahrieva 1 hodinu pri tej istej teplote, pričom pri reakcii vznikajúci metanol sa postupné odstraňuje destiláciou. Potom sa teplota zvýši na 130 až 135 °C a udržiava sa po dobu 5 hodin. V tomto čase oddestiluje zvyšná časť reakčného metanolu a teplota sa zvýši na 160 °C. Po odstranění rozpúšťadla sa reakčná zmes pri nezmenenej teplote podrobí vakuu (š0,l kPa) a v priebehu dalších 3 hodin sa z reakčnej zmesi postupné odstráni nadbytočnýTo a reaction mixture consisting of 0,979 g (0,002 mol) of 2,3-bis (1,2,2,6,6-pentamethyl-4-piperidyloxy) butanedioic acid dimethyl ester II and 0,25 g (0,004 mol) of 1,2-ethanediol in 10 ml of dry xylene heated to 110 DEG C. are treated with 0.05 g of tetrapropyltitanate as a catalyst, and the mixture is heated at the same temperature for 1 hour, during which the methanol formed is gradually removed by distillation, then the temperature is raised to 130-135 DEG At this time, the remainder of the methanol is distilled off and the temperature is raised to 160 DEG C. After removal of the solvent, the reaction mixture is subjected to vacuum (0.5 kPa) at an unchanged temperature and from the reaction mixture for a further 3 hours. gradually eliminate the redundant
1,2-etándiol. Po ochladení sa surový polymér rozpustí v 20 ml toluénu a přečistí sa aktívnym uhlím. Toluén sa odpaří na vákuovej rotačnej odparke a takto izolovaný polyester sa vysuší vo vákuovej sušiarnl pri teplote 120 °C a tlaku 0,1 kPa po dobu 4 hodin. Získaný sklovitý, 1'ahko spráškovateíný, žltkastý produkt vykazuje teplotu topenia v rozmedzí 49 až 60 °C, a Mn = 2 520. Elementárna analýza pre C26H46O6N21,2-ethanediol. After cooling, the crude polymer was dissolved in 20 ml of toluene and purified with charcoal. The toluene is evaporated in a vacuum rotary evaporator and the thus recovered polyester is dried in a vacuum oven at 120 ° C and 0.1 kPa for 4 hours. The glassy, easy-to-dust, yellowish product obtained shows a melting point in the range of 49-60 ° C, and M n = 2,520. Elemental analysis for C 26 H 46 O 6 N 2
Vypočítané: N = 5,80 °/oCalculated: N = 5.80 ° / o
Nájdené: N = 5,62 %Found: N = 5.62%
IČ spektrum (chloroform)IR spectrum (chloroform)
Tmax = 2 980, 2 920, 2 820, 1 740, 1 635,Tmax = 2,980, 2,920, 2,820, 1,740, 1,635,
460, 1 450, 1 390, 1 370, 1 320, 1 280, 1 255,460, 1,450, 1,390, 1,370, 1,320, 1,280, 1,255,
190, 1 150 cm1 Příklad 2190, 1150 cm 1 Example 2
Postupuje sa ako v příklade 1 s tým rozdielom, že k polykondenzácii sa použije dietylester kyseliny 2,3-bis(l,2,2,6,6-pentametyl) butándiovej a ako katalyzátor metanDlát sodný, pričom sa získá žltkastý práškovitý produkt (Mn = 1780) s teplotou topenia v rozmedzí 51 až 62 °C.The procedure is as in Example 1 except that the polycondensation is 2,3-bis (1,2,2,6,6-pentamethyl) butanedioic acid diethyl ester and sodium methanolate catalyst as the catalyst to give a yellowish powdered product (M n = 1780), mp 51-62 ° C.
Vynález má použitie pre svetelnú stabilizáciu polymérov, najma polyolefínov.The invention has applications for light stabilization of polymers, in particular polyolefins.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS859498A CS252976B1 (en) | 1985-12-19 | 1985-12-19 | Poly(ethylene-2,3-bis/1,2,2,6,6-pentamethyl-4-piperidyloxy/butandionate)and method of its production |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS859498A CS252976B1 (en) | 1985-12-19 | 1985-12-19 | Poly(ethylene-2,3-bis/1,2,2,6,6-pentamethyl-4-piperidyloxy/butandionate)and method of its production |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS949885A1 CS949885A1 (en) | 1987-03-12 |
| CS252976B1 true CS252976B1 (en) | 1987-10-15 |
Family
ID=5445048
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS859498A CS252976B1 (en) | 1985-12-19 | 1985-12-19 | Poly(ethylene-2,3-bis/1,2,2,6,6-pentamethyl-4-piperidyloxy/butandionate)and method of its production |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS252976B1 (en) |
-
1985
- 1985-12-19 CS CS859498A patent/CS252976B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS949885A1 (en) | 1987-03-12 |
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