CS252983B1 - Polyamide on base of 2,3-bis (1,2,2,6,6-pentamethyl-4-piperidyloxy)butandione acid and method of its preparation - Google Patents
Polyamide on base of 2,3-bis (1,2,2,6,6-pentamethyl-4-piperidyloxy)butandione acid and method of its preparation Download PDFInfo
- Publication number
- CS252983B1 CS252983B1 CS859510A CS951085A CS252983B1 CS 252983 B1 CS252983 B1 CS 252983B1 CS 859510 A CS859510 A CS 859510A CS 951085 A CS951085 A CS 951085A CS 252983 B1 CS252983 B1 CS 252983B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- piperidyloxy
- pentamethyl
- bis
- preparation
- polyamide
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 5
- 239000004952 Polyamide Substances 0.000 title claims description 4
- 229920002647 polyamide Polymers 0.000 title claims description 4
- 239000002253 acid Substances 0.000 title description 2
- WMNGJUPENSTXBB-UHFFFAOYSA-N 1-(1,2,2,6,6-pentamethylpiperidin-4-yl)oxybutane-2,3-dione Chemical compound CN1C(CC(CC1(C)C)OCC(C(C)=O)=O)(C)C WMNGJUPENSTXBB-UHFFFAOYSA-N 0.000 title 1
- 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 5
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 5
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 4
- -1 alkyl titanate Chemical compound 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-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
- 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
- 239000008096 xylene Substances 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000004611 light stabiliser Substances 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- 150000003384 small molecules Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002329 infrared spectrum 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
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Hydrogenated Pyridines (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
Vynález sa týká polyamidu na báze kyseliny 2,3-bis (1,2,2,6,6-pentametyl-4-piperidyloxyjbutándiove] a sposobu jeho přípravy.The present invention relates to a 2,3-bis (1,2,2,6,6-pentamethyl-4-piperidyloxy) butanedioic acid polyamide and a process for its preparation.
Stéricky bráněné aminy sa vyznačuju vysokou fotostabilizačnou účinnosťou v různých polyméroch, najma polyolefínoch. Nevýhodou nizkomolekulových zlúčenín tfejto skupiny je ich značná prchavosť, vykvetanie a extrahovatefnošť z polymérnych materiálov.The sterically hindered amines are characterized by high photostabilizing activity in various polymers, in particular polyolefins. A disadvantage of the low molecular weight compounds of this group is their considerable volatility, flowering and the extractability of polymeric materials.
Riešenie týchto problémov může poskytnúť použitie stabilizátorov s vyššou molekulovou hmotnosťou.The use of higher molecular weight stabilizers may provide a solution to these problems.
Podstatou vynálezu je polyamid na báze kyseliny 2,3-bis (1,2,2,6,6-pentamety l-4-piperidyloxyjbutándiovej vzorca I fiThe present invention provides a 2,3-bis (1,2,2,6,6-pentamethyl-4-piperidyloxy) butanedioic acid polyamide of formula (I):
C- CH — C H-C-NH-(cfy£NH-C-CH-C-H-C-NH- (cfy £ NH-
kde n je 2 až 100. Podstatou vynálezu je dalej sposob přípravy zlúčeniny I, ktorý sa vyznačuje tým, že sa na dialkylestery kyselinywherein n is 2 to 100. The present invention further provides a process for the preparation of compound I, characterized in that the dialkyl esters of
2,3-bis (1,2,2,6,6-pentametyl-4-piperidyloxyjbutándiovej vzorca II2,3-bis (1,2,2,6,6-pentamethyl-4-piperidyloxy) butanedio (II)
kde R je metylová alebo etylová skupina, posobí 1,6-hexándiamínom III v suchom xylene v přítomnosti metanolátu sodného, lítiumamidu alebo tetraalkyltitanátu pri teplote v rozmedzí od 110 do 160 °C po dobu 6 až 10 hodin.wherein R is methyl or ethyl, it is treated with 1,6-hexanediamine III in dry xylene in the presence of sodium methoxide, lithium 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 hmotnosťou, ktorý do značnej miery může 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 can largely eliminate the aforementioned drawbacks of the low molecular weight compounds of this group.
PřikladlEXAMPLE
K reakčnej zmesi pozostávajúcej z 0,979 gramu (0,002 molu] dimetylesteru kyselinyTo a reaction mixture consisting of 0.979 g (0.002 mol) of dimethyl acid ester
2,3-bis (1,2,2,6,6-pentametyl-4-piperidyloxy)butándiovej, 0,232 g (0,002 móluj 1,6-hexándiamínu v 10 ml suchého toluénu, zahriatej na 110 °C sa přidá 0,05 g lítiumamidu ako katalyzátora. Zmes sa zahrieva 1 hodinu pri tej istej teplote, pričom časť reakčného metanolu sa pomaly oddestiluje. Potom sa teplota zvýši na 130 až 135 °C a udržiava sa po dobu 5 hodin. Počas tejto doby oddestiluje zvyšná časť reakčného metanolu 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 ml 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 °C a tlaku 0,2 kPa po dobu 4 hodin sa získá tuhý, biely 1'ahko spráškovatetný polymér s teplotou máknutia v rozmedzí 79 až 83 °C, ktorý vykazuje pri použití metódy VPO priemernú číselnú molekulovú hmotnost v rozmedzí hodnot 2 600 až 2 700.2,3-bis (1,2,2,6,6-pentamethyl-4-piperidyloxy) butanedioic acid, 0.232 g (0.002 mol of 1,6-hexanediamine) in 10 ml of dry toluene heated to 110 ° C was added 0.05 The mixture is heated at the same temperature for 1 hour, while a portion of the methanol is slowly distilled off, then the temperature is raised to 130-135 ° C and maintained for 5 hours, during which time the remainder of the methanol 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 an unchanged temperature.After cooling, the crude polymer is dissolved in 20 ml of toluene, purified with charcoal, thoroughly washed with distilled water. Evaporation of toluene and drying of the residue in a vacuum oven at 120 ° C and 0.2 kPa pressure for 4 hours gave a solid, white, easily dustable polymer having a softening temperature of 79-83 ° C, which, when used in the VPO method, has an average number molecular weight in the range of 2 600 to 2 700.
Příklad 2Example 2
Pri polykondenzácii 1,025 g (0,002 móluj dietylesteru kyseliny 2,3-bis (1,2,2,6,6-peňtametyl-4-piperidyloxy)butándiovej a 0,232 g (0,002 móluj 1,6-hexándiamínu sa postupuje rovnako ako v příklade 1 len s tým rozdielom, že ako katalyzátor sa použije metanolát sodný pri celkovej době reakcie 6 hodin. Získá sa tuhý biely 1'ahko spráškovatel'ný polymér s teplotou maknutia v rozmedzí 78 až 82 °C, ktorý má pri použití metódy VPO priemernú číselnú molekulovú hmotnost v rozmedzí hodnot 1 700 až 1 850.The polycondensation of 1.025 g (0.002 mol) of 2,3-bis (1,2,2,6,6-pentamethyl-4-piperidyloxy) butanedioic acid diethyl ester and 0.232 g (0.002 mol of 1,6-hexanediamine) proceed as in Example 1. except that sodium methoxide is used as the catalyst for a total reaction time of 6 hours to give a solid, white, dustable polymer having a melt temperature of 78-82 ° C and having an average number molecular weight using VPO. a mass in the range of 1 700 to 1 850.
Elementárna analýza pre C30H56N4O4Elemental analysis for C 30 H 56 N 4 O 4
Vypočítané: N = 10,48 %Calculated: N = 10.48%
Nájdené: N = 10,24 %Found: N = 10.24%
IČ spektrum (chloroform)IR spectrum (chloroform)
350 (str) — υ (N—H, amid),350 (p) - υ (N-H, amide),
980 (s),980 (s)
910 (sj - vas, vs (C-H),910 (sj - in as , in s (CH),
820 (vyb) — v (N—CH3),820 (f) - v (N — CH3),
1720 (s) — v (C=O),1720 (s) - in (C = O),
1430 (str) — á (CH2),1430 (p) - p (CH2),
390 + 1 370 (s) dublet — 5S (gem. CH3),390 + 1370 (s) doublet - 5 S (gem. CH 3 ),
1330 (sl) — v (C—N) cm1 1330 (sl) - v (C-N) cm -1
Vynález má použitie pre přípravu oligomérneho, až polymérneho světelného stabilizátora polymérov, najmá polyolefínov.The invention has application 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 |
|---|---|---|---|
| CS859510A CS252983B1 (en) | 1985-12-19 | 1985-12-19 | Polyamide on base of 2,3-bis (1,2,2,6,6-pentamethyl-4-piperidyloxy)butandione acid and method of its preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS859510A CS252983B1 (en) | 1985-12-19 | 1985-12-19 | Polyamide on base of 2,3-bis (1,2,2,6,6-pentamethyl-4-piperidyloxy)butandione acid and method of its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS951085A1 CS951085A1 (en) | 1987-03-12 |
| CS252983B1 true CS252983B1 (en) | 1987-10-15 |
Family
ID=5445111
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS859510A CS252983B1 (en) | 1985-12-19 | 1985-12-19 | Polyamide on base of 2,3-bis (1,2,2,6,6-pentamethyl-4-piperidyloxy)butandione acid and method of its preparation |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS252983B1 (en) |
-
1985
- 1985-12-19 CS CS859510A patent/CS252983B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS951085A1 (en) | 1987-03-12 |
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