CS252977B1 - Hydrogen sulphate of 2,2,6,6-tetramethyl-4,4-piperidinium acetic acid and method of its preparation - Google Patents
Hydrogen sulphate of 2,2,6,6-tetramethyl-4,4-piperidinium acetic acid and method of its preparation Download PDFInfo
- Publication number
- CS252977B1 CS252977B1 CS859499A CS949985A CS252977B1 CS 252977 B1 CS252977 B1 CS 252977B1 CS 859499 A CS859499 A CS 859499A CS 949985 A CS949985 A CS 949985A CS 252977 B1 CS252977 B1 CS 252977B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- tetramethyl
- piperidinium
- preparation
- acetic acid
- hydrogen sulphate
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 title description 4
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 title description 2
- 229920000642 polymer Polymers 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 239000012153 distilled water Substances 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 239000004611 light stabiliser Substances 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- LNNULQXGQIEGCC-UHFFFAOYSA-N acetic acid;sulfuric acid Chemical compound CC(O)=O.CC(O)=O.OS(O)(=O)=O LNNULQXGQIEGCC-UHFFFAOYSA-N 0.000 claims 2
- 150000002009 diols Chemical class 0.000 claims 1
- 238000006068 polycondensation reaction Methods 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 239000006096 absorbing agent Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000000463 material Substances 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
- 229920000728 polyester Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 1
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Description
Stéricky bráněné aminy sú v porovnaní s klasickými UV-absorbérmi mimoriadne účinné světelné stabilizátory polymérov. Inhibujú nežiadúce radikálové procesy, ktoré sprevádzajú fotooxidačnú degradáciu polymérov, najma polyolefínov. Nevýhodou mnohých zlúčenín tejto skupiny je ich značná prchavosť, vykvétanie a extrahovatelnosť z polymérnych materiálov. Riešenie týchto problémov poskytuje zvyšovanie molekulovej hmotnosti týchto stabilizátorov, alebo naviazanie účinného skeletu na hlavný reťazec úžitkového polyméru. V literatúre doslal' nie je známa zlúčenina, ktorá je predmetom vynálezu. Podstatou vynálezu je hydrogénsíran kyseliny 2,2,6,6-tetrametyl-4-piperidíniumdioctovej vzorca ISterically hindered amines are particularly effective light stabilizers of polymers compared to conventional UV absorbers. They inhibit undesirable radical processes that accompany photooxidative degradation of polymers, especially polyolefins. A disadvantage of many compounds of this group is their high volatility, flowering and extractability from polymeric materials. A solution to these problems is provided by increasing the molecular weight of these stabilizers, or by attaching an effective backbone to the backbone of the useful polymer. The compound of the present invention is not known in the literature. The present invention provides 2,2,6,6-tetramethyl-4-piperidinium di-acetic acid bisulfate
Predmetnú látku možno připravit tak, že sa na amóniovú sol' l,5-dikyano-3,4-dioxo-8,8,10,10-tetrametyl-3,9-diazaspiro [ 5,5 ] undekánu vzorca IIThe subject compound can be prepared by treating the ammonium salt of 1,5-dicyano-3,4-dioxo-8,8,10,10-tetramethyl-3,9-diazaspiro [5,5] undecane of formula II
O, ho''· h3c CH<0, ho " h 3 c CH <
CH~CH ~
OHOH
HSQ$ (DHSQ $ (D
NCNC
H3CH 3 C
H^CH + C
C CC C
J-CN pósobí koncentrovanou kyselinou sírovou a potom sa k reakčnej zmesi přidá destilovaná voda a reakčná zmes sa zahrieva po dobu 6 až 10 h pri teplote 80 až 100 °C.The J-CN is treated with concentrated sulfuric acid, then distilled water is added to the reaction mixture, and the reaction mixture is heated at 80 to 100 ° C for 6-10 h.
Uvedená látka má využitie na přípravu polymérnych světelných stabilizátorov polyesterového typu so zníženou extrahovatel'nosťou z polymérov.Said substance is used for the preparation of polyester type light stabilizers with reduced extractability from polymers.
Příklad 1Example 1
K 1,53 g (0,005 molu) amóniovej soli 1,5252977To 1.53 g (0.005 mol) of the ammonium salt 1.5252977
-dikyano-2,4-dioxo-8,8,10,10-tetrametyl-3,9-diazaspiro'[5,5]undekánu sa přidá 1,5 mililitra koncentrované] kyseliny sírové], zmes sa opatrné zahrieva, pričom systém nadobúda viskóznu konzistenciu. Po štátí réakčne] zmesi cez noc sa na druhý deň k nej přidá 2 ml destilovanej vody a roztok sa nechá zahrievať pri teplote 80 °C po dobu 10 hodin. Z reakčnej zmesi sa počas tejto doby uvolňuje reakčný oxid uhličitý. Po ochladení na 15 °C z roztoku kryštalizuje produkt v podobě bezfarebných priehladných kryštálkov, ktoré sa odsajú a premyjú malým množstvom studenej destilované] vody. Získá sa 1,52 g produktu (85,9%) s teplotou topenia 217 až 220 °C.-dicyano-2,4-dioxo-8,8,10,10-tetramethyl-3,9-diazaspiro [5.5] undecane is added 1.5 ml of concentrated] sulfuric acid], the mixture is heated gently while the system is heated. it has a viscous consistency. After standing overnight, 2 ml of distilled water was added thereto the next day and the solution was allowed to warm to 80 ° C for 10 hours. During this time, the reaction carbon dioxide is released from the reaction mixture. After cooling to 15 ° C from the solution, the product crystallizes as colorless transparent crystals, which are aspirated and washed with a small amount of cold distilled water. 1.52 g of product (85.9%) with a melting point of 217-220 ° C are obtained.
Elementárna analýza pre CisHzsNOsS Vypočítané:Elemental Analysis for C 18 H 18 NO 3 S Calculated:
C = 43,93 %, H = 7,09%, N = 3,94%C = 43.93%, H = 7.09%, N = 3.94%
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS859499A CS252977B1 (en) | 1985-12-19 | 1985-12-19 | Hydrogen sulphate of 2,2,6,6-tetramethyl-4,4-piperidinium acetic acid and method of its preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS859499A CS252977B1 (en) | 1985-12-19 | 1985-12-19 | Hydrogen sulphate of 2,2,6,6-tetramethyl-4,4-piperidinium acetic acid and method of its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS949985A1 CS949985A1 (en) | 1987-03-12 |
| CS252977B1 true CS252977B1 (en) | 1987-10-15 |
Family
ID=5445053
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS859499A CS252977B1 (en) | 1985-12-19 | 1985-12-19 | Hydrogen sulphate of 2,2,6,6-tetramethyl-4,4-piperidinium acetic acid and method of its preparation |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS252977B1 (en) |
-
1985
- 1985-12-19 CS CS859499A patent/CS252977B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS949985A1 (en) | 1987-03-12 |
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