CS252979B1 - Poly(ethylene-2,5-bis/2,2,6,6-tetramethyl-4-piperidyloxy/hexandionate)and method of its preparation - Google Patents
Poly(ethylene-2,5-bis/2,2,6,6-tetramethyl-4-piperidyloxy/hexandionate)and method of its preparation Download PDFInfo
- Publication number
- CS252979B1 CS252979B1 CS859501A CS950185A CS252979B1 CS 252979 B1 CS252979 B1 CS 252979B1 CS 859501 A CS859501 A CS 859501A CS 950185 A CS950185 A CS 950185A CS 252979 B1 CS252979 B1 CS 252979B1
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- CS
- Czechoslovakia
- Prior art keywords
- tetramethyl
- bis
- piperidyloxy
- preparation
- poly
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical group OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 3
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 claims description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 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
- 239000008096 xylene Substances 0.000 claims description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims 2
- BSVJMAJAIMASQV-UHFFFAOYSA-N CC(C)(C1)NC(C)(C)CC1OC(CCC(C(O)=O)OC1CC(C)(C)NC(C)(C)C1)C(O)=O Chemical compound CC(C)(C1)NC(C)(C)CC1OC(CCC(C(O)=O)OC1CC(C)(C)NC(C)(C)C1)C(O)=O BSVJMAJAIMASQV-UHFFFAOYSA-N 0.000 claims 1
- 229960000250 adipic acid Drugs 0.000 claims 1
- 235000011037 adipic acid Nutrition 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- -1 2,2,6,6-tetramethyl-4-piperidyloxy Chemical group 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000004611 light stabiliser Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- WHAQPJRAVIDEQN-UHFFFAOYSA-N CCOC(C(CCC(C(OCC)=O)OC1CC(C)(C)NC(C)(C)C1)OC1CC(C)(C)NC(C)(C)C1)=O Chemical compound CCOC(C(CCC(C(OCC)=O)OC1CC(C)(C)NC(C)(C)C1)OC1CC(C)(C)NC(C)(C)C1)=O WHAQPJRAVIDEQN-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- HKJYVRJHDIPMQB-UHFFFAOYSA-N propan-1-olate;titanium(4+) Chemical compound CCCO[Ti](OCCC)(OCCC)OCCC HKJYVRJHDIPMQB-UHFFFAOYSA-N 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Description
Riešenie týchto problémov može poskytnut použitie vhodných polymérnych stabilizátorov. Podstatou vynálezu je poly[etylén-2,5-bis(2,2,6,6-tetrametyl-4-piperidyloxy)hexándionát] vzorca IThe use of suitable polymeric stabilizers can provide a solution to these problems. The present invention provides a poly [ethylene-2,5-bis (2,2,6,6-tetramethyl-4-piperidyloxy) hexanedionate] of the formula I
kde n je 2 až 100. Podstatou vynálezu je ďalej sposob přípravy zlúčeniny I, ktorý sa vyznačuje tým, že sa na dialkylestery kyseliny 2,5-bis(2,2,6,6-tetrametyl-4-piperidylo xyjhexándiovej vzorca IIwherein n is from 2 to 100. The present invention further provides a process for the preparation of compound I which is characterized in that to 2,5-bis (2,2,6,6-tetramethyl-4-piperidyloxyhexanedioic acid dialkyl esters II)
kde R je metylová, alebo etylová skupina, působí 1,2-etándiolom v suchom xylene v přítomnosti metanolátu sodného, lítiumamidu, alebo tetraalkyltitanátu pri teplote v rozmedzí od 110 do 160 °C po dobu 7 až 10 hodin.wherein R is methyl or ethyl, treated with 1,2-ethanediol in dry xylene in the presence of sodium methanolate, lithium amide, or tetraalkyl titanate at a temperature ranging from 110 to 160 ° C for 7 to 10 hours.
Výhodou uvedeného vynálezu je příprava oligomérneho, až polymérneho světelného stabilizátora polyalkylpiperidínového typu so zvýšenou molekulovou hmotnosfou, který pri aplikácii v polymérnych materíáloch může do značnej miery eliminovat spomínané nedostatky vyskytujúce sa u nízkomolekulových zlúčenín tejto skupiny.An advantage of the present invention is the preparation of an oligomeric to polymeric light stabilizer of polyalkylpiperidine type with increased molecular weight which, when applied in polymeric materials, can largely eliminate the aforementioned drawbacks occurring in the low molecular weight compounds of this group.
Přiklad 1Example 1
K reakčnej zmesi pozostávajúcej z 0,51 g (0,001 molu] dietylesteru kyseliny 2,5-bis(2,2,6,6-tetrametyl-4-piperidyloxy)hexándiovej, 0,125 g (0,002 molu] 1,2-etándiolu v 10 ml suchého toluénu, zahriatej na 110 °C sa přidá 0,03 g tetrapropyltitanátu ako katalyzátore. Zmes sa zahrieva 1 h pri tej istej teplote, pričom část reakčného etanolu sa postupné oddestiluje. Potom sa teplota zvýši na 130 až 135 °C a udržiava sa po dobu 5 hodin. Počas tejto doby oddestiluje zvyšná část reakčného etanolu a teplota sa zvýši na 160 °C. Po odstránení rozpúšťadla sa zvyšok pri nezmenenej teplote podrobí vákuu 0,1 kPa po dobu dalších 4 hodin. Po ochladení sa surový polymér rozpustí v 20 mililitroch toluénu, přečistí aktívnym uhlím, dokladné premyje destilovanou vodou a roztok sa vysuší bezvodým síranom sodným. Po odpaření toluénu a vysušení zvyšku vo vákuovej sušiarni pri teplote 120 °G a tlaku 0,2 kPa po dobu 4 h, sa získá tuhý, žltkastý, křehký polymér s teplotou máknutia 72 až 75 °C a priemernou číselnou molekulovou hmotnosfou 2 800.To a reaction mixture consisting of 0.51 g (0.001 mol) of 2,5-bis (2,2,6,6-tetramethyl-4-piperidyloxy) hexanedioic acid diethyl ester, 0.125 g (0.002 mol) of 1,2-ethanediol in 10 ml of dry toluene heated to 110 [deg.] C. is added 0.03 g of tetra-propyltitanate as a catalyst, and the mixture is heated at the same temperature for 1 hour, while part of the reaction ethanol is gradually distilled off, then raised to 130-135 [deg.] C. During this time, the remainder of the ethanol is distilled off and the temperature is raised to 160 DEG C. After removal of the solvent, the residue is subjected to a vacuum of 0.1 kPa for a further 4 hours at unchanged temperature. After toluene is evaporated and the residue is dried in a vacuum oven at 120 ° C and 0.2 kPa for 4 h, a solid, yellowish solid is obtained. 100% brittle, brittle polymer with a softening point of 72-75 ° C and an average molecular weight of 2,800.
P r i k 1 a d 2Example 1 and d 2
Pri polykondenzácii 0,483 g (0,001 mólu) dimetylesteru kyseliny 2,5-bis(2,2,6,6-tetrametyl-4-piperidyloxy)hexándlovej a 0,125 g (0,002 mólu) 1,2-etándiolu sa postupuje ako v příklade 1 len s tým rozdielom, že ako katalyzátor sa použije lítiumamid v množstve 0,03 g a reakčná zmes sa zahrieva 7 h v rozmedzí teplůt 110 až 160 °C. Získá sa tuhý, žltkastý, l'ahko spráškovateTný polymér, ktorý vykazuje teplotu maknutla v rozmedzí· 73 až 77 °C a priemernú číselná molekulová hmotnost 3100, (pri stanovení pomocou VPO).The polycondensation of 0.483 g (0.001 mol) of 2,5-bis (2,2,6,6-tetramethyl-4-piperidyloxy) hexanedioic acid dimethyl ester and 0.125 g (0.002 mol) of 1,2-ethanediol is followed as in Example 1 only with the difference that 0.03 g of lithium amide is used as the catalyst and the reaction mixture is heated for 7 h in a temperature range of 110 to 160 ° C. A solid, yellowish, easily dustable polymer is obtained which has a melt temperature in the range of 73-77 ° C and an average molecular weight of 3100 (as determined by VPO).
Elementárna analýza pre C26H46N2O6Elemental analysis for C 26 H 46 N 2 O 6
Vypočítané: N = 5,80 %Calculated: N = 5.80%
Nájdené: N = 5,73 %Found: N = 5.73%
IC spektrum (chloroform)IC spectrum (chloroform)
360 (s) — v (N—H),360 (s) - in (N-H),
980 (s),980 (s)
940 (s) - uas, vs (C-H),940 (s) - at as , in s (CH),
1740 (s) v (C=O),1740 (s) in (C = O),
1450 (s) — S (C—H),1450 (s) -S (C-H),
380 (s) + 1 360 (s) dublet — 5 (gem.380 (s) + 1,360 (s) doublet - 5 (gem.
CH3),CH 3 ),
1300 (s) — v (C—H),1300 (s) - in (C-H),
260 (s) + 1240 (s) — v (C—O—C ester) cm-1 260 (s) + 1240 (s) - in (C-O-C ester) cm -1
Vynález má použitie pre přípravu oligomérneho, až polymérneho světelného stabilizátora polymérov, najma polyolefínov.The invention is of use for the preparation of an oligomeric to polymeric light stabilizer of polymers, in particular polyolefins.
PREDMET VYNALEZUOBJECT OF THE INVENTION
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS859501A CS252979B1 (en) | 1985-12-19 | 1985-12-19 | Poly(ethylene-2,5-bis/2,2,6,6-tetramethyl-4-piperidyloxy/hexandionate)and method of its preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS859501A CS252979B1 (en) | 1985-12-19 | 1985-12-19 | Poly(ethylene-2,5-bis/2,2,6,6-tetramethyl-4-piperidyloxy/hexandionate)and method of its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS950185A1 CS950185A1 (en) | 1987-03-12 |
| CS252979B1 true CS252979B1 (en) | 1987-10-15 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS859501A CS252979B1 (en) | 1985-12-19 | 1985-12-19 | Poly(ethylene-2,5-bis/2,2,6,6-tetramethyl-4-piperidyloxy/hexandionate)and method of its preparation |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS252979B1 (en) |
-
1985
- 1985-12-19 CS CS859501A patent/CS252979B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS950185A1 (en) | 1987-03-12 |
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