CS254696B1 - 3,3-bis/chlormethyl/-1,5-dioxa-8,8,10,10-tetramethyl-9-azaspiro/5,5/undecane and process for preparing thereof - Google Patents
3,3-bis/chlormethyl/-1,5-dioxa-8,8,10,10-tetramethyl-9-azaspiro/5,5/undecane and process for preparing thereof Download PDFInfo
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- CS254696B1 CS254696B1 CS867370A CS737086A CS254696B1 CS 254696 B1 CS254696 B1 CS 254696B1 CS 867370 A CS867370 A CS 867370A CS 737086 A CS737086 A CS 737086A CS 254696 B1 CS254696 B1 CS 254696B1
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- tetramethyl
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- azaspiro
- undecane
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- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 title abstract description 11
- 238000004519 manufacturing process Methods 0.000 title 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000002904 solvent Substances 0.000 claims abstract description 7
- 239000000203 mixture Substances 0.000 claims abstract description 6
- 239000008096 xylene Substances 0.000 claims abstract description 5
- 150000003738 xylenes Chemical class 0.000 claims abstract description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 4
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 4
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 4
- YFESJHPTNWYOCO-UHFFFAOYSA-N loprodiol Chemical compound OCC(CO)(CCl)CCl YFESJHPTNWYOCO-UHFFFAOYSA-N 0.000 claims abstract description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims abstract 2
- 238000006555 catalytic reaction Methods 0.000 claims 1
- JWUXJYZVKZKLTJ-UHFFFAOYSA-N Triacetonamine Chemical compound CC1(C)CC(=O)CC(C)(C)N1 JWUXJYZVKZKLTJ-UHFFFAOYSA-N 0.000 abstract description 10
- 238000002360 preparation method Methods 0.000 abstract description 10
- 229920000642 polymer Polymers 0.000 abstract description 9
- 150000001875 compounds Chemical class 0.000 abstract description 7
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 abstract description 6
- 239000004611 light stabiliser Substances 0.000 abstract description 6
- 238000000034 method Methods 0.000 abstract description 6
- -1 polytioethers Polymers 0.000 abstract description 5
- 239000003377 acid catalyst Substances 0.000 abstract description 3
- 229920000515 polycarbonate Polymers 0.000 abstract description 3
- 239000004417 polycarbonate Substances 0.000 abstract description 3
- 238000006068 polycondensation reaction Methods 0.000 abstract description 3
- 229920000728 polyester Polymers 0.000 abstract description 3
- 229920000570 polyether Polymers 0.000 abstract description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 229920006295 polythiol Polymers 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 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
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 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
- 239000002775 capsule Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 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
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 238000007539 photo-oxidation reaction Methods 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
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- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Riešenie sa týká 3,3-bis(clilórmetyl)-1,5- -dioxo-S.S.lOjlO-tetrametyl-O-azaspiro[ 5,5 ] - undekánu vzorca I a sposobu jeho přípravy, ktorý spočívá v tom, že ša nechá reagovat 2,2,6,6-tetrametyl-4-oxopiperidín vzorca II s l,3-dichlór-2,2-dihydroxyrnety.lpropánom vzorca III pri teplote spatného toku uhlovodíkového rozpúšfadla, ktoré vytvára s vodou azeotropickú zmes, ako je například benzén, toluén alebo xyleny, za přítomnosti kyslého katalyzátora, ako je například kyselina 4-toluénsulfónová. Zlúčenina vzorca I má použitie ako světelný stabilizátor pre polyméry a na přípravu polymérnych světelných stabilizátorov polykondenzačnými reakciami, přípravu polyéterov, polytioéterov, polyesterov alebo polykarbonátov.The solution relates to 3,3-bis (chloromethyl) -1,5- -dioxo-S.S.1O10.1-tetramethyl-O-azaspiro [5,5] - undecane of formula I and the process for its preparation, which is to allow the reaction to react 2,2,6,6-tetramethyl-4-oxopiperidine of formula II s 1,3-dichloro-2,2-dihydroxymethylpropane of formula III at the hydrocarbon backflow temperature a solvent that forms with water an azeotropic mixture such as benzene, toluene or xylenes, in the presence of an acid catalyst such as e.g. 4-toluenesulfonic acid. Compound of Formula I has use as a light stabilizer for polymers and for preparing polymers light stabilizers by polycondensation reactions, the preparation of polyethers, polytioethers, polyesters or polycarbonates.
Description
Riešenie sa týká 3,3-bis (clilórmetyl )-1,5-dioxo-S.S.lOjlO-tetrametyl-O-azaspiro [ 5,5 ] undekánu vzorca I a sposobu jeho přípravy, ktorý spočívá v tom, že ša nechá reagovatThe present invention relates to 3,3-bis (chloromethyl) -1,5-dioxo-S.S.10,10-tetramethyl-O-azaspiro [5,5] undecane of formula I and a process for the preparation thereof by reacting it
2,2,6,6-tetrametyl-4-oxopiperidín vzorca II s l,3-dichlór-2,2-dihydroxyrnety.lpropánom vzorca III pri teplote spatného toku uhlovodíkového rozpúšfadla, ktoré vytvára s vodou azeotropickú zmes, ako je například benzén, toluén alebo xyleny, za přítomnosti kyslého katalyzátora, ako je například kyselina 4-toluénsulfónová. Zlúčenina vzorca I má použitie ako světelný stabilizátor pre polyméry a na přípravu polymérnych světelných stabilizátorov polykondenzačnými reakciami, přípravu polyéterov, polytioéterov, polyesterov alebo polykarbonátov.2,2,6,6-tetramethyl-4-oxopiperidine of formula II with 1,3-dichloro-2,2-dihydroxyrnethylpropane of formula III at a low flow temperature of a hydrocarbon solvent which forms an azeotropic mixture with water, such as benzene, toluene or xylenes, in the presence of an acid catalyst such as 4-toluenesulfonic acid. The compound of formula I has utility as a light stabilizer for polymers and for the preparation of polymeric light stabilizers by polycondensation reactions, the preparation of polyethers, polythioethers, polyesters or polycarbonates.
Ch/„- Cl z xtCh / n-Cl of xt
CH~ Cl ( I )CH-Cl (I)
Vynález sta týká 3,3-bis(chlórmetyl)-l,;5-dioxa-8,8,-0,10-tetrametyl-9-azaspiro[5,5]undekánu a sposobu jeho přípravy.The present invention relates to 3,3-bis (chloromethyl) -1,5-dioxa-8,8, -0,10-tetramethyl-9-azaspiro [5,5] undecane and a process for its preparation.
Stéricky tienené aminy patria v súčasnosti medzi najúčinnejšie světelné stabilizátory pre polyméry [F. E. Karrer, Makromol. Chem., 181, 595 (1980), J. J. Usilton, A. R. Patel, Amer. Chem. Soc. Polym. Prep., 18 (1), 393 (1977), F. Guguinus, Developments in Polymer Stabilisation-1, ed. G. Scott, Applied Svience Publishers, London, 1979, kap. 8.) Sú to rozličné deriváty 2,2,6,6-tetraalkylpiperidínu, 1,2,2,6,6-pentaalkylpiperidínu,Sterically shielded amines are currently among the most effective light stabilizers for polymers [F. E. Karrer, Makromol. Chem., 181, 595 (1980), J. J. Usilton, A. R. Patel, Amer. Chem. Soc. Polym. Prep., 18 (1), 393 (1977), by F. Guguinus, Developments in Polymer Stabilization-1, ed. G. Scott, Applied Svience Publishers, London, 1979, Chap. 8.) These are various derivatives of 2,2,6,6-tetraalkylpiperidine, 1,2,2,6,6-pentaalkylpiperidine,
2,2,6,6-tetraalkylpiperazínu alebo 7,15-diazadispiro[5,l,5,3jhexadekánu. Tieto zlúčeniny inhibujú nežiadúce degradačné reakcie, ktoré prebiehajú pri fotooxidácii polymérov, najma polyolefínov. Nevýhodou světelných stabilizátorov triedy stéricky tienených amínov je ich vysoká prchavosť a extrahovatel'nosť z úžitkových polymérov. Přípravou zlúčeniny, ktorá je predmetom vynálezu sa zvýši molekulová hmotnost' stabilizátora, čo zníži prchavosť a extrahovateínosť stabilizátora z polymérov. Přítomnost funkčných chlórmetylových skupin súčasne umožňuje přípravu polymérnych stabilizátorov polykondenzačnými reakciami, přípravu polyéterov, polytioéterov, polyesteroví a polykarbonátov. Látka, ktorá je predmetom vynálezu doteraz neholá popísaná v odbornej literatúre, podstatou vynálezu je 3,3-bis(chlórmetyl)-Í,5-dioxa-8,8,10,lO-tetrametyl-9-azaspiro[5,5!]undekán vzorca I.2,2,6,6-tetraalkylpiperazine or 7,15-diazadispiro [5.1.1] hexadecane. These compounds inhibit the undesirable degradation reactions that occur during photooxidation of polymers, especially polyolefins. The disadvantage of the light stabilizers of the class of sterically shielded amines is their high volatility and extractability from utility polymers. By preparing the compound of the invention, the molecular weight of the stabilizer is increased, which decreases the volatility and extractability of the polymer stabilizer. At the same time, the presence of functional chloromethyl groups allows the preparation of polymeric stabilizers by polycondensation reactions, the preparation of polyethers, polythioethers, polyester and polycarbonates. The substance of the present invention has not yet been described in the scientific literature and is based on 3,3-bis (chloromethyl) -1,5-dioxa-8,8,10,10-tetramethyl-9-azaspiro [5,5!] undecane of formula I.
t,Ct·’-.T, C · "-.
\/ '0 -Ch, z C m, - Cl \ , - Ύ\ / '0 -Ch, from C m, - Cl \, - Ύ
Η -N /\ / ' \ , /\ 0-Cho Cw,-Ci / 4- óΗ -N / / (/), Ch-Ch o Cw, -Ci / 4-6
Podstatou vynálezu je ďalej sposob přípravy zlúčeniny vzorca I, vyznačujúci sa tým, že 2,2,6,6-tetrametyl-4-oxopiperidín vzorca IIThe present invention further provides a process for the preparation of a compound of formula I, characterized in that 2,2,6,6-tetramethyl-4-oxopiperidine of formula II
Cí -H Ch 3 Cl -H Ch 3
VaVa
Η -M,Η -M,
XX
C t-í i ‘5 { II i reaguje s l,3-dichlór-2,2-dihydroxymetylpropánom vzorca IIIC 1 H 15 (II) is reacted with 1,3-dichloro-2,2-dihydroxymethylpropane of formula III
H—O—CH2 CH2—C1H — O — CH2 CH2 - C1
H—O—CH2 CH2—Cl (III) pri teplote spatného toku uhlovodíkového rozpúšťadia, ktoré tvoří s vodou azeotropickú zmes, ako je například benzén, toluén alebo xylény, za přítomnosti kyslého katalyzátore, ako je například kyselina 4-toluénsulfónová.H - O - CH 2 CH 2 - Cl (III) at a low flow temperature of a hydrocarbon solvent which forms an azeotropic mixture with water such as benzene, toluene or xylenes in the presence of an acid catalyst such as 4-toluenesulfonic acid.
Příklad 1Example 1
Do banky, opatrenej nástavcem na azeotropické oddelovanie vody a, spatným chladičom, sa vloží 15,5 g (0,1 mólu) 2,2,6„6-tetrametyl-4-oxopiperidínu, 20 gi (0 105 molu) kyseliny 4-toluénsulfónovej χ 1H2O a 200 ml benzénu. Reakčná zmes sa zahrieva pri teplote spatného toku 1 hodinu, pričom sa oddělí kryšlálová voda z kyseliny a vlhkost zo· systému. Súčasne vzniká sof kyseliny a derivátu piperidinu. Potom sa přidá 17,3 g (0,1 molu j l,3-dichlór-2,2-dihydroxymetylpropánu. Reakčná zmes sa ďalej refluxuje, pokial' sa v azeottropickom nástavci nevylúči teoretické množstvo vody. Potom sa ochladená reakčná zmes vleje do chladného 20 %-ného vodného roztoku hydroxidu sodného· a dobré pretrepe. Oddělí sa organická vrstva, ktorá sa premýva vodou a solankou a vysuší bezvodým síranom sodným. Oddestiluje sa rozpúšťadlo a získá sa tuhý koláč v množstve 30 g (97 % teoretického výtažku], ktorý sa prekryštalizuje z hexánu. Získá sa zlúčenina vzorca I ako biela krystalická látka s teplotou topenia 86 až 87 °C.In a flask equipped with an azeotropic water separator and a reflux condenser, 15.5 g (0.1 mole) of 2,2,6,6-tetramethyl-4-oxopiperidine, 20 g (0 105 mole) of 4- acid are charged toluene sulfone χ 1 H 2 O and 200 ml benzene. The reaction mixture was heated at reflux for 1 hour, separating the crystalline water from the acid and the moisture from the system. At the same time, a salt of the acid and piperidine derivative is formed. Then 17.3 g (0.1 mol) of 1,3-dichloro-2,2-dihydroxymethylpropane are added. The reaction mixture is further refluxed until the theoretical amount of water is precipitated in the azeotropic capsule. The organic layer was washed with water and brine and dried over anhydrous sodium sulfate, and the solvent was distilled off to give a solid cake (30 g, 97%). Recrystallization from hexane gave the compound of formula I as a white crystalline solid, m.p. 86-87 ° C.
Elementárna analýza pre:Elemental analysis for:
C14H25CI2NO2 vypočítané:C14H25Cl2NO2 calculated:
iC 54,19 %, H 8,12 %, N 4,51 %, nájdené: ! 1 ! iC 54.19%, H 8.12%, N 4.51%, found :! 1!
C 54,25 %, H 8,39 %, N 4,42 %.C 54.25%, H 8.39%, N 4.42%.
1H NMR spektrum (CDCls) á (ppm): 1 H NMR spectrum (CDCl 3)? (Ppm):
1,13 (š, —CH3, 12H),1.13 (br, —CH3, 12H),
1,60 (s, — ΟΗ2--, 4H),1.60 (s, -ΟΗ2--, 4H),
3,62 (s, —CH2—Cl, 4H),3.62 (s, —CH2 — Cl, 4H),
3,70 (s, —1CH2—Ο—, 4H).3.70 (s, -1 CH 2 -, 4H).
P r í k 1 a d 2Example 1 a d 2
Postupuje sa rovnako ako v příklade 1 s tým rozdielom, že sa ako rozpúšťadlo použije zmes xylénov s teplotou varu v rozmedzí 137 až 140 °Ό. Získá sa 30 g (97 % teoretického výtažku) surového produktu.The procedure was as in Example 1 except that the solvent used was a mixture of xylenes boiling in the range of 137 to 140 ° Ό. 30 g (97% of theory) of the crude product are obtained.
Příklad 3Example 3
100 hmotnostných dielov nestabilizovaného práškovitého polypropylénu sa impregnuje v dichlórmetáne s 0,1 hmot. dielmi 2,6-di-terc.butyl-4-metylfenolu, 0,15 hmot. diela stearanu vápenatého a s 0,2 hmot. diela zlúčeniny, pripravenej podfa příkladu 1. Po karbionylového pása v infračervených spektrách. Kým doba dosiahnutia karbonylového indexu 0,2 u čistého polypropylénu je 220 hodin, stabilizovaný polymér dosiahne túto hodnotu až po 1 780 hodinách.100 parts by weight of unstabilized powdered polypropylene are impregnated in dichloromethane with 0.1 wt. parts by weight of 2,6-di-tert-butyl-4-methylphenol, 0.15 wt. % of calcium stearate and 0.2 wt. parts of the compound prepared according to Example 1. Following the carbionyl band in infrared spectra. While the time of reaching the carbonyl index of 0.2 for pure polypropylene is 220 hours, the stabilized polymer does not reach this value until 1780 hours.
odpaření rozpúšťadlá sa zo zmesi vylisují! fólie O' hrúbke 0,2 mm pri tlaku 20 MPa a teplote 190 °C po dobu 5 minút. Takto připravené fólie sa ožarujú ortuťovou výbojkou o výkone 125 W vo vzdialenosti 7 cm od zdroja. Degradácia polyméru sa sleduje vývojomevaporation of the solvents is pressed from the mixture! 0.2 mm thick film at a pressure of 20 MPa and a temperature of 190 ° C for 5 minutes. The films thus prepared are irradiated with a 125 W mercury lamp at a distance of 7 cm from the source. The degradation of the polymer is monitored by development
PREDMETSUBJECT
1. 3,3-bis (chlórmetyl j-l,5-dioxa-8,8,10,10-tetrametyl-9-azaspiro[5,5]undekán vzorca I.1. 3,3-Bis (chloromethyl) -1,5-dioxa-8,8,10,10-tetramethyl-9-azaspiro [5,5] undecane of formula I.
ch3 ci-i^ch 3 ci-i
Ct.Ct.
/ \/ /V Q-CU., CM- C i./ \ / / In Q-CU., CM-C i.
CR, { í !CR, {i!
2. Sposob přípravy 3,3-bis(chlórmetylj-l,5-dioxa-8,8,10,10-tetrametyl-9-azaspiro|[ 5;5 ] undekánu vzorca I, podta bodu 1, vyznačujúci sa tým, že 2,2,6,6-tetrametyl-4-oxopiperidín vzorca II2. A process for the preparation of 3,3-bis (chloromethyl) -1,5-dioxa-8,8,10,10-tetramethyl-9-azaspiro [5; 5] undecane of formula I, according to claim 1, characterized in that 2,2,6,6-tetramethyl-4-oxopiperidine of formula II
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS867370A CS254696B1 (en) | 1986-10-13 | 1986-10-13 | 3,3-bis/chlormethyl/-1,5-dioxa-8,8,10,10-tetramethyl-9-azaspiro/5,5/undecane and process for preparing thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS867370A CS254696B1 (en) | 1986-10-13 | 1986-10-13 | 3,3-bis/chlormethyl/-1,5-dioxa-8,8,10,10-tetramethyl-9-azaspiro/5,5/undecane and process for preparing thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS737086A1 CS737086A1 (en) | 1987-05-14 |
| CS254696B1 true CS254696B1 (en) | 1988-01-15 |
Family
ID=5422718
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS867370A CS254696B1 (en) | 1986-10-13 | 1986-10-13 | 3,3-bis/chlormethyl/-1,5-dioxa-8,8,10,10-tetramethyl-9-azaspiro/5,5/undecane and process for preparing thereof |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS254696B1 (en) |
-
1986
- 1986-10-13 CS CS867370A patent/CS254696B1/en unknown
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| Publication number | Publication date |
|---|---|
| CS737086A1 (en) | 1987-05-14 |
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