CS215303B1 - Migh-molecular stabilizers for the piperazine type polymeres and method of making the same - Google Patents
Migh-molecular stabilizers for the piperazine type polymeres and method of making the same Download PDFInfo
- Publication number
- CS215303B1 CS215303B1 CS364580A CS364580A CS215303B1 CS 215303 B1 CS215303 B1 CS 215303B1 CS 364580 A CS364580 A CS 364580A CS 364580 A CS364580 A CS 364580A CS 215303 B1 CS215303 B1 CS 215303B1
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- Prior art keywords
- polymers
- molecular weight
- migh
- polymeres
- making
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- 229920000642 polymer Polymers 0.000 title claims description 15
- 239000003381 stabilizer Substances 0.000 title description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 title 2
- 238000004519 manufacturing process Methods 0.000 title 1
- 239000004611 light stabiliser Substances 0.000 claims description 6
- 238000009835 boiling Methods 0.000 claims description 4
- 239000003822 epoxy resin Substances 0.000 claims description 4
- 239000000155 melt Substances 0.000 claims description 4
- 229920000647 polyepoxide Polymers 0.000 claims description 4
- 239000000376 reactant Substances 0.000 claims description 4
- 125000003700 epoxy group Chemical group 0.000 claims description 3
- 230000008018 melting Effects 0.000 claims description 3
- 238000002844 melting Methods 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 239000012454 non-polar solvent Substances 0.000 claims description 3
- 239000002798 polar solvent Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- ZOSPIRSWAQIPSU-UHFFFAOYSA-N 7,15-diazadispiro[5.1.5^{8}.3^{6}]hexadecane Chemical compound C1CCCCC21NC1(CCCCC1)CNC2 ZOSPIRSWAQIPSU-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000000051 modifying effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000002103 osmometry Methods 0.000 description 1
- 238000010525 oxidative degradation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000005201 scrubbing Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
Landscapes
- Epoxy Resins (AREA)
Description
Podstata sposobu přípravy vyššiemolekulových světelných stabilizátorov pre polymery piperazínového typu spočívá v tom, že sa na zlúčeninu vzorca IIThe essence of the preparation of higher molecular weight light stabilizers for piperazine-type polymers consists in:
HH
NN
teplotách medzi teplotou topenia a 250 °C alebo v roztoku organických rozpúštadiel pri teplotách do teploty varu rozpúšťadla sa pdsobí epoxidovou živicou s koncovými epoxidovými skupinami s molekulovou hmotnosťou 340 až 4000.at temperatures between the melting point and 250 ° C or in a solution of organic solvents at temperatures up to the boiling point of the solvent are treated with an epoxy resin having terminal epoxy groups having a molecular weight of 340 to 4000.
Vynález má použitie na přípravu světelných stabilizátorov pre polyméry.The invention is used for preparing light stabilizers for polymers.
v tavenine reakčných zložiek priin the melt of the reactants at
Vynález sa týká zlúčeniny obecného vzorca IThe invention relates to a compound of formula I
-CH2—CH—CHa—O—V o ! x -CH 2 —CH — CH and —O —Vo! x
OHOH
CH3 >— CÍCH,,CH 3 > - CHILD ,,
O >-0O> -0
OH nOH n
kde η = 1 až 10.where η = 1 to 10.
V polyméroch pod vplyvom tepla, světla a kyslíka prebiehajú rozličné degradačné procesy, leh dóslekom je zhoršovanie fyzlkálno-chemlckých vlastností polymérov, nakol'ko počas degradácie dochádza k znižovaniu molekulové) hmotnosti vzniku nenasýtených štruktúr karbonylových skupin atd. Vonkajším prejavom týchto procesov je znižovánie pevnosti polymérov, křehkost, sfarbovanie a změna dalších fyzlkálnochemlckých vlastností. Na retardáciu a inhibíclu degradácie pridávajú sa k polymérom rozličné zlúčeniny, ktoré predlžujú životnost výrobkov z polymérov. Podl'a róznych podmienok ich použitia možno ich rozdělit na antioxidanty, ktoré sú účinné pri termickej a termooxldačnej degradácil a světelné stabilizátory, ktoré zlepšujú fotooxidačnú odolnost polymérov.Different degradation processes take place in polymers under the influence of heat, light and oxygen. The external manifestation of these processes is a decrease in the strength of the polymers, brittleness, coloring and a change in other physical-chemical properties. To retard and inhibit degradation, various compounds are added to the polymers to extend the life of the polymer articles. According to different conditions of their use, they can be divided into antioxidants which are effective in thermal and thermo-oxidative degradation and light stabilizers which improve the photo-oxidative resistance of the polymers.
U nízkomolekulových stabilizátorov, světelných aj termooxidačných, dochádza počas spracovanla a používania polymérov k znižovaniu ich koncentrácie v polymére v dosledku fyzikálnych strát sposobených ich prchavosťou alebo vypieratelnosťou. Zvýšenie molekulovej hmotnosti stabilizátorov podía předmětu vynálezu eliminuje alebo znižuje tieto straty a to tiež pri vysokoteplotnom spracovaní stabilizovaných úžitkových polymérov. Vynález sa týká přípravy světelných stabilizátorov pre polyméry, ktoré sa vyznačujú tým, že majú vo svojej molekule stéricky bráněný amin vzorca II.In low molecular weight stabilizers, both light and thermo-oxidizing, their concentration in the polymer decreases during processing and use of the polymers due to physical losses caused by their volatility or scrubbing. The increase in the molecular weight of the stabilizers of the present invention eliminates or reduces these losses, also in the high temperature treatment of stabilized utility polymers. The invention relates to the preparation of light stabilizers for polymers, characterized in that they have a sterically hindered amine of formula II in their molecule.
HH
NN
HH
Sposob přípravy podía vynálezu sa vyznačuje tým, že na zlúčeninu vzorca II sa v tavenine reakčných zložiek pri teplotách medzi teplotou topenia a 250 °C, alebo v roztoku organických polárných alebo nepolárných rozpúšťadiel pri teplotách do teploty varu rozpúšťadla sa posobí epoxidovou živicou s koncovými epoxidovými skupinami s molekulovou hmotnosťou 340 až 4000.The process according to the invention is characterized in that the compound of the formula II is admixed in the melt of the reactants at temperatures between melting point and 250 ° C or in a solution of organic polar or non-polar solvents at temperatures up to the boiling point. having a molecular weight of 340 to 4000.
Reakcia zlúčeniny vzorca II a epoxidovej živice sa prevádza v tavenine homogenizovaných reakčných zložiek v inertnej atmosféře, alebo v roztoku polárných aj nepolárných rozpúšťadiel pri teplotách do teploty varu rozpúšťadla. Tieto stabilizátory sa okrem stabilizačného účinku vyznačujú pri vyšších hodnotách n aj modifikačným účinkom v systémoch s úžitkovými polymérmi.The reaction of the compound of formula II and the epoxy resin is carried out in the melt of the homogenized reactants in an inert atmosphere, or in a solution of both polar and non-polar solvents at temperatures up to the boiling point of the solvent. In addition to the stabilizing effect, these stabilizers have a modifying effect in systems with useful polymers at higher n values.
Uvedené příklady ilustrujú, ale vobec nevyčerpávajú ani neobmedzujú rozsah nášho vynálezu.These examples illustrate but do not generally limit or limit the scope of our invention.
Příklad 1Example 1
Do sklenenej ampule sa po zabezpečení inertnej atmosféry vniesla homogenizovaná zmes 3,4 g 2,2-bis4-/2,3-epoxypropoxy/fenyl propánu a 4,44 g 7,15-diazadispiro-[5,1,5,3]-hexadekánu. Reakčný systém sa po zatavení ampule zahrieval na teplotu 120 °C po dobu 3 hodin. Po tejto době sa v reakčnej zmesi nezistiii žladne epoxidové skupiny (analytický postup: V. Vorobjov, Chem. Průmysl, 13/38, 381 (1963). Získaná látka vo formě nažltlej sklovitej masy mala t. t. = 46—50 °C. Elemenárna analýza pre C49H76N4O4:A homogenized mixture of 3.4 g of 2,2-bis4- (2,3-epoxypropoxy) phenyl propane and 4.44 g of 7,15-diazadispiro- [5,1,5,3] was added to the glass vial after the inert atmosphere was ensured. -hexadecane. The reaction system was heated to 120 ° C for 3 hours after sealing the vial. After this time, no epoxy groups were detected in the reaction mixture (analytical procedure: V. Vorobjov, Chem. Průmysl, 13/38, 381 (1963). The obtained substance in the form of a yellowish glassy mass had mp = 46-50 ° C. for C49H76N4O4:
Vypočítané:calculated:
C = 75,0 %; H = 9,69 %; N = 7,14 %C = 75.0%; H = 9.69%; N = 7.14%
Nájdené:found:
C = 75,89 %; H = 10,11 %; N = 7,02 %C = 75.89%; H = 10.11%; N = 7.02%
Příklad 2:Example 2:
Do banky, opatrenej miešadlom, spatným chladičom, prívodom a odvodom dusíka sa vnieslo 43 g epoxidovej živíce s obsahom glycidylových skupin 6%, 11,1 g 7,15-diazadispiro- [5,1,5,3] — hexadekánu a 100 ml xylénu. Pomalým zahrievaním sa teplota reakčnej zmesi za prebublávania dusíkem zvyšovala behom 3 hodin na 100 °C. Potom sa roztok zahrieval na teplotu 130 °C po dobu 6 hodin. Po ukončení reakcie sa oddestiloval za zníženého tlaku xylén a získal sa reakčný produkt vo formě nažltlej sklovitej masy. Produkt sa rozpustil v chloroforme a vyzrážal do metanolu. Získal sa biely prášok produktu. Osmometriou v parnej fáze sa zistila číselná molekulová hmotnost: Mn = 2000.Into a flask equipped with a stirrer, a reflux condenser, a nitrogen inlet and an outlet, 43 g of an epoxy resin containing 6% glycidyl groups, 11.1 g of 7,15-diazadispiro- [5,1,5,3] hexadecane and 100 ml were charged. xylene. Slowly heating the temperature of the reaction mixture to 100 ° C with nitrogen bubbling. Then the solution was heated to 130 ° C for 6 hours. After completion of the reaction, xylene was distilled off under reduced pressure to obtain the reaction product as a yellowish glassy mass. The product was dissolved in chloroform and precipitated into methanol. A white powder of the product was obtained. The molecular weight was determined by vapor phase osmometry: M n = 2000.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS364580A CS215303B1 (en) | 1980-05-23 | 1980-05-23 | Migh-molecular stabilizers for the piperazine type polymeres and method of making the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS364580A CS215303B1 (en) | 1980-05-23 | 1980-05-23 | Migh-molecular stabilizers for the piperazine type polymeres and method of making the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS215303B1 true CS215303B1 (en) | 1982-08-27 |
Family
ID=5377090
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS364580A CS215303B1 (en) | 1980-05-23 | 1980-05-23 | Migh-molecular stabilizers for the piperazine type polymeres and method of making the same |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS215303B1 (en) |
-
1980
- 1980-05-23 CS CS364580A patent/CS215303B1/en unknown
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