CS252978B1 - Polyamide containing structural units of 2,5-bis(2,2,6,6-tetramethyl-4-piperidyloxy)hexandionic acid and method of its preparation - Google Patents
Polyamide containing structural units of 2,5-bis(2,2,6,6-tetramethyl-4-piperidyloxy)hexandionic acid and method of its preparation Download PDFInfo
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- CS252978B1 CS252978B1 CS859500A CS950085A CS252978B1 CS 252978 B1 CS252978 B1 CS 252978B1 CS 859500 A CS859500 A CS 859500A CS 950085 A CS950085 A CS 950085A CS 252978 B1 CS252978 B1 CS 252978B1
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- Czechoslovakia
- Prior art keywords
- bis
- piperidyloxy
- tetramethyl
- preparation
- structural units
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 5
- 229920002647 polyamide Polymers 0.000 title claims description 4
- 239000004952 Polyamide Substances 0.000 title claims description 3
- 239000002253 acid Substances 0.000 title 1
- 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 group 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 description 5
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 4
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-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
- 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000004611 light stabiliser Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 150000003384 small molecules Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000003381 stabilizer 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
- UDSFAEKRVUSQDD-UHFFFAOYSA-N Dimethyl adipate Chemical compound COC(=O)CCCCC(=O)OC UDSFAEKRVUSQDD-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 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
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material 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
- 239000000843 powder Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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- Polyamides (AREA)
Description
Vynález sa týká polyamidu na báze kyseliny 2,5-bis (2,2,6,6-tetrametyl-4-piperidyloxyJhexándiovej a sposobu jeho přípravy.The invention relates to a polyamide based on 2,5-bis (2,2,6,6-tetramethyl-4-piperidyloxy) hexanedioic acid and a process for its preparation.
Stéricky bráněné aminy sú význačnou triedou světelných stabilizátorov polymérov. Nevýhodou nízkomolekulových zlúčenín tejto skupiny je ich prchavosť, extrahovateínosť a toxicita.Sterically hindered amines are a prominent class of polymer light stabilizers. The disadvantages of the low molecular weight compounds of this group are their volatility, extractability and toxicity.
Uvedené nedostatky rieši zabudovanie stabilizátore do úžitkového polyméru alebo použitie stabilizátora s vyššou molekulovou hmotnosťou. Podstatou vynálezu je polyamid obsahujúci štruktúrne jednotky kyseliny 2,5-bis (2,2,6,6-tetrametyl-4-piperidyloxy) hexándiovej vzorca IThese disadvantages are solved by incorporating the stabilizer into the useful polymer or by using a higher molecular weight stabilizer. The present invention provides a polyamide containing the structural units of 2,5-bis (2,2,6,6-tetramethyl-4-piperidyloxy) hexanedioic acid 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 xy Jhexándiovej vzorca IIwherein n is from 2 to 100. The present invention further provides a process for the preparation of a compound of the formula I, characterized in that 2,5-bis (2,2,6,6-tetramethyl-4-piperidyloxy) hexanedioic acid II is dialkyl esters
kde R je metylová, alebo etylová skupina, působí 1,6-hexándiamínom III v suchom xylene v přítomnosti metanolátu sodného, 11tiumamidu, alebo tetraalkyltitanátu pri teplotě v rozmedzí od 110 do 160 °C po dobu 6 až 10 hodin.wherein R is a methyl or ethyl group, treated with 1,6-hexanediamine III in dry xylene in the presence of sodium methoxide, 11thium amide, or tetraalkyl titanate at a temperature ranging from 110 to 160 ° C for 6 to 10 hours.
Výhodou uvedeného vynálezu je příprava oligomérneho, až polymérneho světelného stabilizátora polyalkylpiperidínového typu so zvýšenou molekulovou hmotnostou, ktorý pri aplikácii v polymérnych materiáloch může do značné] 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 of increased molecular weight which, when applied in polymeric materials, can largely eliminate the aforementioned drawbacks of the low molecular weight compounds of this group.
Příklad 1Example 1
K reakčnej zmesi pozostávajúcej z 0,51 g (0,001 mólu) dietylesteru kyseliny 2,5-bis(2,2,6,6-tetrametyl-4-piperidyloxy)hexándiovej, 0,116 g (0,001 mólu) 1,6-hexándiamínu v 10 ml suchého toluénu, zahriatej na 110 °C sa přidá 0,03 g metanolátu sodného ako katalyzátora. Zmes sa zahrieva 1 h pri tej istej teplote, pričom časť 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 časť reakčného etanolu a teplota sa zvýši na 160 °C. Po odstránení rozpúšťadla sa zvyšok pri nezmenej teplote podrobil vákuu 0,1 až 0,2 kPa po dobu dalších 4 hodin. Po ochladení sa surový polymér rozpustí v 20 ml toluénu, přečistí aktívnym uhlím, důkladné premyje destilovanou vodou a roztok sa vysuší bezvodým síranom sodným. Po odpaření toluénu a vysušení zvyšku vo vakuové] sušiarni pri teplote 120 °C a tlakuTo 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, 0.116 g (0.001 mol) of 1,6-hexanediamine in 10 ml of dry toluene heated to 110 [deg.] C. is added 0.03 g of sodium methanolate as a catalyst. The mixture is heated at the same temperature for 1 h, while part of the ethanol is gradually distilled off. The temperature is then raised to 130-135 ° C and maintained for 5 hours. During this time, the remainder of the ethanol was distilled off and the temperature was raised to 160 ° C. After removal of the solvent, the residue was subjected to a vacuum of 0.1 to 0.2 kPa at a constant temperature for an additional 4 hours. After cooling, the crude polymer was dissolved in 20 ml of toluene, treated with charcoal, washed extensively with distilled water, and dried over anhydrous sodium sulfate. After evaporating the toluene and drying the residue in a vacuum oven at 120 ° C and pressure
0,2 kPa po dobu 4 hodin, sa získal tuhý, biely, 1'ahko spráškovatelný polymér s teplotou máknutia 96 až 102 °C s priemernou číselnou molekulovou hmotnostou v rozmedzí hodnůt 1800 až 1950 (pri použití VPO).0.2 kPa over 4 hours, a solid, white, easy-to-dust powder polymer having a softening point of 96-102 ° C with an average molecular weight ranging from 1800 to 1950 (using VPO) was obtained.
Příklad 2Example 2
Pri polykondenzácii 0,483 g (0,001 mólu) dimetylesteru kyseliny 2,5-bis(2,2,6,6-tetrainetyl-4-plperidyloxy)hexándiovej a 0,116 g (0,001 mólu) 1,6-hexándiamínu sa postupuje rovnako ako v příklade 1, len s tým rozdielom, že ako katalyzátor sa použije lítiumamid a celková doba reakcie je 6 hodin. Získá sa tuhý biely, 1'ahko spracovatelný polymér s teplotou máknutia 98 až 103 °C, s priemernou číselnou molekulovou hmotnostou v rozmedzí 3 000 až 3 300.The polycondensation of 0.483 g (0.001 mol) of 2,5-bis (2,2,6,6-tetrainethyl-4-plperidyloxy) hexanedioic acid dimethyl ester and 0.116 g (0.001 mol) of 1,6-hexanediamine was carried out as in Example 1. except that lithium amide is used as the catalyst and the total reaction time is 6 hours. A white solid, easy-to-process polymer having a softening temperature of 98 to 103 ° C, with an average molecular weight in the range of 3,000 to 3,300, is obtained.
Elementárna analýza pre C28H52N4O4Elemental analysis for C 28 H 52 N 4 O 4
Vypočítané: N — 11,01 %Calculated: N - 11.01%
Nájdené: N — 10,65 %Found: N - 10.65%
IČ spektrum (chloroform)IR spectrum (chloroform)
370 (str) — v (N-H, amid),370 (p) - in (N-H, amide),
980 (s),980 (s)
930 (s) — vas, vs (C-H),930 (s) - in as , in s (CH),
720 (s) — v (C=O),720 (s) - in (C = O),
450 (str) — δ (CHz),450 (p) - δ (CH 2),
390 + 1 370 (s) dublet — ds (gem. CH3),390 + 1370 (s) doublet - d s (gem. CH 3 ),
320 (sl) — 1» (C-N) cm1 320 (sl) -1 (CN) cm -1
Vynález má použitie pre přípravu oligomérneho, až polymérneho světelného stabilizátora polymérov, najmS polyolefínov.The invention has utility for the preparation of an oligomeric to polymeric light stabilizer of polymers, in particular polyolefins.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS859500A CS252978B1 (en) | 1985-12-19 | 1985-12-19 | Polyamide containing structural units of 2,5-bis(2,2,6,6-tetramethyl-4-piperidyloxy)hexandionic acid and method of its preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS859500A CS252978B1 (en) | 1985-12-19 | 1985-12-19 | Polyamide containing structural units of 2,5-bis(2,2,6,6-tetramethyl-4-piperidyloxy)hexandionic acid and method of its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS950085A1 CS950085A1 (en) | 1987-03-12 |
| CS252978B1 true CS252978B1 (en) | 1987-10-15 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS859500A CS252978B1 (en) | 1985-12-19 | 1985-12-19 | Polyamide containing structural units of 2,5-bis(2,2,6,6-tetramethyl-4-piperidyloxy)hexandionic acid and method of its preparation |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS252978B1 (en) |
-
1985
- 1985-12-19 CS CS859500A patent/CS252978B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS950085A1 (en) | 1987-03-12 |
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