CS216273B1 - Polymerizable luminous stabilizers of the piperazine type - Google Patents
Polymerizable luminous stabilizers of the piperazine type Download PDFInfo
- Publication number
- CS216273B1 CS216273B1 CS345580A CS345580A CS216273B1 CS 216273 B1 CS216273 B1 CS 216273B1 CS 345580 A CS345580 A CS 345580A CS 345580 A CS345580 A CS 345580A CS 216273 B1 CS216273 B1 CS 216273B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- polymerizable
- stabilizers
- luminous
- piperazine
- piperazine type
- Prior art date
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- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 title 2
- 239000003381 stabilizer Substances 0.000 title 1
- 239000004611 light stabiliser Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 4
- -1 diethyl 2,5-dibromohexanoate Chemical compound 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 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
- WCQBVYMYTSEPKC-UHFFFAOYSA-N 7,15-diazadispiro[5.1.5^{8}.3^{6}]hexadecane-14,16-dione Chemical compound N1C2(CCCCC2)C(=O)NC(=O)C21CCCCC2 WCQBVYMYTSEPKC-UHFFFAOYSA-N 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 159000000000 sodium salts Chemical class 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- KABAKEOYQZKPBA-UHFFFAOYSA-N 2,5-dibromohexanedioic acid Chemical compound OC(=O)C(Br)CCC(Br)C(O)=O KABAKEOYQZKPBA-UHFFFAOYSA-N 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- 241000219745 Lupinus Species 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000012259 ether extract Substances 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
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N methyl monoether Natural products COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 238000005201 scrubbing Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
Description
(54) Polymerizovatelné světelné stabilizátory piperazínového typu(54) Polymerizable piperazine-type light stabilizers
Vynález s.a týká polymerizovateíných derivátov stéricky bráněných piperazínov všeobecného vzorca:The invention relates to polymerizable derivatives of sterically hindered piperazines of the general formula:
> ' fH - GH2 - GH2 - CH - CH - <X> f H - GH 2 - GH 2 - CH - CH - <X
RORO
CWD óCdCWD óCd
OR a spósoibu ich přípravy, kde R značí metylová alebo etylovú skupinu.OR and a process for their preparation, wherein R represents a methyl or ethyl group.
- Spósoib přípravy týchto zlúčenín, ktoré nie sú známe z literatúry, sa zakladá na reakcii dimetyl- alebo dietyleisteru kyseliny 2,5-di-brómhexandiovej s 7,15-diazadiispiro- [5,1,5, 3] -hexadekán-14,16-diónom.- The method for the preparation of these compounds, which are not known from the literature, is based on the reaction of 2,5-di-bromohexanedioic acid dimethyl or diethyl ether with 7,15-diazadiispiro- [5,1,5,3] -hexadecane-14, 16-dione.
Uvedené zlúčeniny móžu samotné plnit funkciu světelných stabilizátorov polymérov. Nevýhodou nízkomolekulových látok patriaciái áo lupiny štěřiéký bráněných ámínov je ich značná prchavosť a vypieratelnosť.These compounds can themselves act as light stabilizers for polymers. The disadvantage of low molecular weight substances belonging to lupine of the hindered amines is their considerable volatility and scrubbing.
Přípravou polymérnych světelných stabilizátorov sa tieto nedostatky odstránia. K tomuto účelu móžu slúžiť látky, ktoré sú predmetom vynálezu.The preparation of polymeric light stabilizers removes these drawbacks. The substances which are the subject of the invention can be used for this purpose.
Příklad 1Example 1
K 2,88 g (0,01 molu) draselnej soli 7,15-diazadispiro-[5,l,5,3] hexadekán -14-16-diónu v 30 ml bezvodého dimetylformamidu sa za stálého miešania pri teplote okolo 80 °C prikvapkáva v priebehu 1/2 až 1 hodiny roztokTo 2.88 g (0.01 mol) of the potassium salt of 7,15-diazadispiro- [1,1,3,3] hexadecane-14-16-dione in 30 ml of anhydrous dimethylformamide was stirred at a temperature of about 80 ° C with stirring. the solution is added dropwise over 1/2 to 1 hour
3,6 g (0,01 molu) dietyleisteru kyseliny 2,5-dibrómhexandiovej v 15 ml bezvodého dimetylformamidu. Zmes sa ďalej zahrieva a mieša po dobu 3 hodin a nechá sa ochladit. Vyextrahuje sa trikrát éterom a spojené éterické extrakty sa dokladné premyjú vodou, vysušia bezvodým síranom sodným a éter sa odpaří. Získaný zvyšok sa prekryštalizuje z etanolu. Získá sa produkt v podobě bielej kryštalickej látky s t.t. — 197—200 °C. Elementárna analýza pre CggHggNjOg:3.6 g (0.01 mol) of 2,5-dibromohexanedioic acid diethyl ether in 15 ml of anhydrous dimethylformamide. The mixture was further heated and stirred for 3 hours and allowed to cool. It is extracted three times with ether and the combined ether extracts are washed thoroughly with water, dried over anhydrous sodium sulphate and the ether is evaporated. The residue is recrystallized from ethanol. Obtained as a white crystalline solid, m.p. - 197-200 ° C. Elemental Analysis for CggHggNjOg:
Vypočítané:calculated:
C = 65,31 %; H = 8,36 %; N = 8,02 % Nájdené:C = 65.31%; H = 8.36%; N = 8.02% Found:
C = 66,40 %; H = 8,50 %; N = 8,05 %C = 66.40%; H = 8.50%; N = 8.05%
IC spektrum(CHCl'j):IC spectrum (CHCl 3):
vmax = 860, 970, 1020, 1075, 1200, 1265, 1340, 1370, 1450, 1680, 1740, 2940. ν max = 860, 970, 1020, 1075, 1200, 1265, 1340, 1370, 1450, 1680, 1740, 2940.
Příklad 2Example 2
100' hmotnostných dielov nestabilizovaného práškovitého polypropylénu sa impregnovalo v dičhlórmetáne s 0,1 hmot. dielmi 2,6-di-terc. butyl-4-metylfenolu, 0,15 hmot. dielmi stearanu vápenatého a s 0,2 hmot. dielmi zlúčeniny, pripravenej podlá příkladu 1. Po odpaření rozpúšťadla sa zo zmesi vylisovali fólie o hrúbke 0,2 mm pri tlaku 20 MPa a teplote 190 °C po dobu 30 sekúnd. Tesne před lisováním sa vzorky ešte predohrievali 1 minútu pri teplote 190 °C. Fólie sa ožarovali ortuťovou výbojkou o výkone 125 W vo vzdialenosti 7 cm od zdroja a ako filter sa použil100 parts by weight of unstabilized powdered polypropylene were impregnated in 0.1% w / w dichloromethane. parts 2,6-di-tert. butyl-4-methylphenol, 0.15 wt. % of calcium stearate and 0.2 wt. After evaporation of the solvent, 0.2 mm thick sheets were pressed from the mixture at 20 MPa at 190 ° C for 30 seconds. Just before pressing, the samples were preheated for 1 minute at 190 ° C. The films were irradiated with a 125 W mercury lamp at a distance of 7 cm from the source and a filter was used
1,6 hmot. % roztok síranu meďnatého. Degradácia polymeru sa sledovala vývojom hydroperoxidového a karbonylového pásu v infračervených spektrách. Kým doba dosiahnutia karbonylového indexu 0,2 u čistého polypropylénu bola 480 hodin, stabilizovaný polymér nedosiahol túto hodnotu ani za 3000 hodin.1.6 wt. % copper sulfate solution. The degradation of the polymer was followed by the development of the hydroperoxide and carbonyl bands in the infrared spectra. While the time of reaching the carbonyl index of 0.2 for pure polypropylene was 480 hours, the stabilized polymer did not reach this value even after 3000 hours.
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS345580A CS216273B1 (en) | 1980-05-19 | 1980-05-19 | Polymerizable luminous stabilizers of the piperazine type |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS345580A CS216273B1 (en) | 1980-05-19 | 1980-05-19 | Polymerizable luminous stabilizers of the piperazine type |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS216273B1 true CS216273B1 (en) | 1982-10-29 |
Family
ID=5374665
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS345580A CS216273B1 (en) | 1980-05-19 | 1980-05-19 | Polymerizable luminous stabilizers of the piperazine type |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS216273B1 (en) |
-
1980
- 1980-05-19 CS CS345580A patent/CS216273B1/en unknown
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