CN1004139B - 温度稳定的液体组合物 - Google Patents
温度稳定的液体组合物 Download PDFInfo
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- C07C205/23—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups having nitro groups and hydroxy groups bound to carbon atoms of six-membered aromatic rings having nitro groups and hydroxy groups bound to carbon atoms of the same non-condensed six-membered aromatic ring having two nitro groups bound to the ring
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Abstract
本发明涉及一类组合物,该组合物含有溶于芳香烃溶剂中的二硝基苯酚和足够量的苯二胺,此苯二胺使溶液中二硝基苯酚的量大于苯二胺不存在时它在溶液中的量。此类组合物具有意想不到的、理想的低温稳定性,并可另外用溶剂稀释用来作为乙烯基芳香化合物聚合反应的阻聚剂。
Description
本发明涉及一种含有溶解于芳香烃溶剂中的二硝基苯酚的液体组合物,此液体组合物还含有足够量的苯二胺,因而使溶液中的二硝基苯酚的量比不存在苯二胺时的量更大。这种组合物具有意想不到的、理想的低温稳定性,可以用对于乙烯基芳香化合物的聚合反应起阻聚作用的溶剂来稀释。
用工业方法所制备的单体苯乙烯、二乙烯基苯和低级烷基化苯乙烯(如α-甲苯乙烯和乙烯基甲苯)等的乙烯基芳香化合物,其产品一般含有各种杂质,如苯、甲苯等。为了使单体产品适合于多种用途,必须将这些杂质除去。通常是用蒸馏的方法来提纯这些乙烯基芳香化合物。
然而,乙烯基芳香化合物容易聚合,其聚合速率随温度升高而迅速增加,这是人所共知的。为了防止蒸馏条件下乙烯基芳香单体的聚合,至今已经采用过各种阻聚剂。
一般而言,工业上用作这种聚合抑制剂的化合物是二硝基苯酚类化合物,例如,Drake等人在美国专利2526567中介绍了用2,6-二硝基苯酚作抑制剂对环上氯代苯乙烯所呈现的稳定作用同样,在美国专利4105506中Watson公开了用2,6-二硝基对甲酚作乙烯基芳香化合物的聚合抑制剂。
最近,Butler人在美国专利4466905中介绍:于氧存在下,在具有2,6-二硝基对甲酚的蒸馏柱中,苯二胺的存在会进一步减少发生聚合的量。
虽然二硝基苯酚类化合物是有效的聚合抑制剂,但使用起来尚有一些缺点,例如,二硝基苯酚是固体,如其温度高于它的熔点就不稳定,并有爆炸的可能(请参见美国专利4457806),所以要大量运输和贮存这类固体物质是不可能的。
因此,必须以溶液的形式运输和贮存这类抑制剂,最好是用与处理乙烯基芳香单体溶剂相匹配的溶剂,一般用低沸点的烃。
令人遗憾的是,在运输和贮存期间所承受的温度范围内,大多数二硝基苯酚在这类优选的溶剂中的溶解度均较低。例如,按质量计,于18℃下,2,6-二硝基对甲酚在乙苯中的溶解度为20%,这个数随着温度降低速度下降,-2℃时为15%,-14℃时为10%,而在-25℃时反为4.2%。一旦这些二硝基苯酚化合物从溶液中沉淀出来,即使其温度再升到原来贮藏温度(例如约18℃)它们也不易再溶解成为溶液。
而且,二硝基苯酚是一类毒性强的物质,其半数致死量(LD50)(大鼠)小于30mg/kg(Sax,工业化学物质的危险性)。
这类二硝基苯酚抑制剂由于毒性强和溶解度低再加上所用溶剂的易燃性,因此使得二硝基苯酚抑制剂在优选剂中的溶溶液其运输和贮存的花费大且有一定的危险性。而且,运输或贮存期间如果由于降低温度此抑制剂便会从溶液中沉淀出来,实际浓度则会远低于名义浓度。
这样如果按名义浓度将此种抑制溶液装入乙烯基芳香化合物的蒸馏柱,于是实际装入蒸馏柱的抑制剂的量降低了,这样由于乙烯基芳香单体的猛烈的聚合作用而导致蒸馏柱的严重破坏。
因此,最好是制备一种能较为安全和经济地进行运输的二硝基苯酚浓缩液。而且最好是一种具有理想的低温稳定性的二硝基苯酚浓缩液。
为此,本发明的目的之一是提供一种二硝基苯酚浓缩液,此浓缩液的闪点比普通的非浓缩溶液的闪点要低,这样运输就比较安全。
本发明的另一个目的是提供这样的一种二硝基苯酚浓缩液,其每一定量的二硝基苯酚所需溶剂的体积较小,因此使运输比较经济。
本发明的第三个目的是提供一种具有理想的低温稳定性的二硝基苯酚溶液。
下面的叙述及实施例将充分体现出上述目的及其它目的。
一方面本发明是关于一种液体组合物,该液体组合物含有下式的二硝基苯酚
其中,R和R1一个为硝基,另一个从氢、氯和C1-C8烷基组成的一组基团中选择,该二硝基苯酚溶于一种芳香烃溶剂;所说的液体组合物还含有足够量的下式苯二胺:
其中R2和R3每个都可单独地从氢、C1-C12烷基、苯基和C1-C8烷基取代的苯基所组成的一组基图中选择。
这样,溶解在所说溶剂中的二硝基苯酚的量比苯二胺不存在时能溶解的二硝基苯酚的量要大。
另一方面,本发明是关于一种低温稳定的液体组合物,它含有:
A)二硝基苯酚,其式为:
其中R和R1一个为硝基,另一个从氢、氯和C1-C8烷基所此组成的组中选择:
B)苯二胺,其式为:
其中R2和R3都可单独地从氢、C1-C12烷基、苯基和CC1-C8烷基取代的苯基所组成的组中选择;以及
C)芳香烃溶剂。
其中组分A与组分B的重量比约在1∶9和9∶1之间;
其中组分A加组分B之与组分C的重量比至少为1∶10。
本发明的这类组合物包括三种组分,即二硝基苯酚、苯二胺和芳香烃溶剂。
可使用的二硝基苯酚是具有以下结构的化合物:
其中R和R1,一个是硝基,另一个是从氢和C1-C8直链或支链烷基所组成的组中选择。优选的二硝基苯酚化合物包括:2,6-二硝基-对-甲酚、4,6-二硝基-邻-甲酚、2,6-二硝基-对-异丙基苯酚、4,6-二硝基-邻-异丙基苯酚和4,6-二硝基-邻-仲-丁基苯酚。
可使用的苯二胺化合物,其化学式为:
其中R2和R3每个均可单独地从氢、C1-C12的直链和支链烷基、苯基、以及被C1-C8烷基取代的苯基所组成的组中选择。一般而言,优选的苯二胺是具有上述结构的化合物,其中的R2是苯基、R3是C3-C8烷基。可使用的优选苯二胺的例子包括:N-苯基-N′-异丙基-对-苯二胺,N-苯基-N′-(1,3-二甲丁基)-对-苯二胺、N-苯基-N′-(1,3-二甲戊基)-对-苯二胺、N,N′-二异丙基-对-苯二胺、N,N′-二-仲-丁基-对-苯二胺和N,N′-二(1,4-二甲戊基)-对-苯二胺。
能使用的芳香烃溶剂是可溶解二硝基苯酚和苯二胺的任何一种液体芳香烃。这类溶剂有:苯、甲苯、二甲苯、乙苯、苯乙烯、乙烯基甲苯、二乙烯基苯、α-甲基苯乙烯和其它烷基化的苯乙烯或烷基苯,所有这些芳香烃溶剂均可从市面上买到。
虽然最优选的溶剂是随本发明的稳定剂组合物的具体用途而变,但被稳定的典型乙烯基芳香化合物及其氢化的前体是优选的溶剂。所以,对于稳定苯乙烯来说,乙苯和苯乙烯本身就是优选的溶剂。同样,对于稳定α-甲基苯乙烯,异丙基苯和α-甲基苯乙烯则是优选的溶剂。
苯二胺存在的量要使溶于上述溶液中的二硝基苯酚的量大于苯二胺不存在时溶解于该溶剂中的二硝基苯酚的量。因此,在给定温度下,实际存在于本发明组合物中的二硝基苯酚的量要大于苯二胺不存在时能溶于所选的芳香烃溶剂中二硝基苯酚的量。
二硝基苯酚和苯二胺之和与芳香烃溶剂的重量比一般至少约为1∶10。虽然正如本技术领域普通技术人员所了解的那样,此优选比将取决于所选的具体组分,也取决于加于此组合物的温度和压力,但其优选比约在1∶4和2∶1之间。
二硝基苯酚和苯二胺的比一般约在9∶1和1∶9之间,优选范围约在3∶2和2∶3之间。
本发明组合物的制备方法是,将所需量的二硝基苯酚和苯二胺按任何顺序加入到一定量的溶剂中,最好是边搅拌边加。
另外,本发明的组合物具有理想的低温稳定性,于18℃下溶于给定溶剂中的二硝基苯酚和苯二胺的总量一般至少约为75%或75%以上,而在-25℃下,同样溶剂的溶液中这个量仍保持不变。
本发明组合物可用来作为聚合抑制剂要另外加一定量的溶剂稀释,稀释后的浓度不超过5%(重量),这样稀的浓度易于输入乙烯基芳香烃反应剂蒸馏柱。
实施例
下述实施例旨在进一步说明本发明,而决不是要限制本发明的范围。
实施例1
在一个宽温度范围内测出4,6-二硝基-邻-甲酚(DNOC)2,6-二硝基-对-甲酚(DNPC)N-异丙基-N′-苯基-对-苯二胺)(Naugard I-4,uniroyal化学公司的商标以下均称“I-4”),以及DNOC或DNPC与I-4的混合物在乙苯中的溶解度。测定方法是,先配制这些纯产品的悬浮液,滤出不溶物,按重量差计算溶解度,这样的实验结果列于下表Ⅰ中:
表Ⅰ 乙苯中的百分溶解度
溶质 18℃ -2℃ -14℃ -25℃
DNOC 19 12 10 4.5
DNPC 20 15 10 4.2
I-4 27 16 12.5 8.2
DNOC/I-4 1/1(重量) 67+ 66 56 53
DNPC/I-4 1/1(重量) 67+ 66 63 58
实施例2
按实施例1的步骤,分别测定DNOC、DNPC、I-4、DNOC或DNPC与I-4的混合物在苯乙烯中的溶解度。实验结果总结于下表Ⅱ中:
表Ⅱ 苯乙烯中的百分溶解度
溶质 18℃ -2℃ -14℃ -25℃
DNOC 25 25 13 6.1
DNPC 25 25 25 18
I-4 30 24 19 14.5
DNOC/I-4 1/1(重量) 67+ 67+ 67+ 67+
DNPC/I-4 1/1(重量) 67+ 67+ 67+ 67+
从表Ⅰ和Ⅱ的数据可以看出:由于苯二胺(I-4)的存在使得溶解在芳香烃溶剂中的二硝基苯酚的量增加了。
因此,例如,DNPC和I-4的1∶1混合物于-25℃下有58%溶于乙苯中,而这些化合物单独地于同样的溶剂、同样的温度下其溶解度分别仅为4.2%和8.2%。因此,此混合物溶解的量比两者相加的溶解量大4倍,在溶液中的DNPC几乎是多了8倍。
而且上述数据还表明了本发明组合物的低温稳定性。例如,1∶1的DNPC和I-4在乙苯中-25℃时的溶解度相对于18℃时它的溶解度而言,保持了大约87%。与此相反,DNPC和I-4单独的溶液在同样的温度范围内它们的溶解度分别仅约为21%和30%。
Claims (18)
1、一种低温下稳定的、可安全运输的液体组合物,该组合物含有:
A)二硝基苯酚,其式为:
其中R和R1一个为硝基,另一个选自氢、氯和C1-C8烷基;
B)苯二胺,其式为
其中R2和R3每个都可单独地选自氢、C1-C12烷基、苯基和被C1-C8烷基取代的苯基,
C)芳香烃溶剂,
其中组分A与组分B之重量比在1∶9和9∶1之间,其中组分A加B与组分C之重量比至少为1∶10。
2、权利要求1的组合物,其中所说的二硝基苯酚从下述化合物组成的组中选择:2,6-二硝基-对甲酚、4,6-二硝基-邻-甲酚、2,6-二硝基-对-异丙苯酚、4,6-二硝基-邻-异丙苯酚和4,6-二硝基-邻-仲-丁苯酚。
3、权利要求1的组合物,其中所说的苯二胺从下述化合物组成的组中选择:N-苯基-N′-异丙基-对-苯二胺,N-苯基-N′-(1,3-二甲丁基)-对-苯二胺、N-苯基-N′-(1,3-二甲戊基)-对-苯二胺、N,N′-二异丙基-对-苯二胺、N,N′-二-仲-丁基-对-苯二胺和N,N′-二(1,4-二甲戊基)-对-苯二胺。
4、权利要求1的组合物,其中所说的芳香烃溶剂从下述化合物组成的组中选择:苯、甲苯、二甲苯、乙苯、苯乙烯、乙烯基甲苯、二乙烯基苯和α-甲基苯乙烯。
5、权利要求1的组合物,其中所说的芳香烃选自苯乙烯和乙苯。
6、权利要求1的组合物,其中所说的二硝基苯酚从2,6-二硝基-对-甲酚、4,6-二硝基-邻-甲酚、2,6-二硝基-对-异丙苯酚、4,6-二硝基-邻-异丙苯酚和4,6-二硝基-邻-仲-丁苯酚所组成的组中选择,
其中所说的苯二胺是从N-苯基-N′-异丙基-对-苯二胺,N-苯基-N′-(1,3-二甲丁基)-对-苯二胺、N-苯基-N′-(1,3-二甲戊基)-对-苯二胺、N,N′-二异丙基-对-苯二胺、N,N′-二-仲-丁基-对-苯二胺和N,N′-二(1,4-二甲戊基)-对-苯二胺所组成的组中选择。
其中所说的芳香烃溶剂是从苯、甲苯、二甲苯、乙苯、苯乙烯、乙烯基甲苯、二乙烯基苯和α-甲基苯乙烯所组成的组中选择。
7、权利要求1或6的组合物,其中二硝基苯酚加苯二胺之和与芳香烃溶剂的重量比在1∶4和2∶1之间。
8、权利要求1或6的组合物,其中二硝基苯酚加苯二胺的重量比在2∶3和3∶2之间。
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Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US817324 | 1986-01-09 | ||
US06/817,324 US4664845A (en) | 1986-01-09 | 1986-01-09 | Phenylenediamine solubilizer for dinitrophenol in aromatic solvent |
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Publication Number | Publication Date |
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CN87100819A CN87100819A (zh) | 1987-09-23 |
CN1004139B true CN1004139B (zh) | 1989-05-10 |
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CN87100819.XA Expired CN1004139B (zh) | 1986-01-09 | 1987-01-08 | 温度稳定的液体组合物 |
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US (1) | US4664845A (zh) |
EP (1) | EP0234671B1 (zh) |
JP (1) | JPH01152146A (zh) |
KR (1) | KR910004552B1 (zh) |
CN (1) | CN1004139B (zh) |
AR (1) | AR245096A1 (zh) |
AT (1) | ATE63534T1 (zh) |
AU (1) | AU595571B2 (zh) |
BR (1) | BR8700050A (zh) |
CA (1) | CA1275168C (zh) |
DE (1) | DE3770019D1 (zh) |
DK (1) | DK11387A (zh) |
ES (1) | ES2022880B3 (zh) |
FI (1) | FI84906C (zh) |
IN (1) | IN166453B (zh) |
MX (1) | MX165080B (zh) |
PT (1) | PT84086B (zh) |
ZA (1) | ZA8769B (zh) |
Families Citing this family (12)
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US4774374A (en) * | 1987-06-12 | 1988-09-27 | Uniroyal Chemical Company, Inc. | Stabilized vinyl aromatic composition |
US4915873A (en) * | 1988-01-22 | 1990-04-10 | Uniroyal Chemical Company, Inc. | Polymerization inhibitor composition for vinyl aromatic compounds |
DE3825163A1 (de) * | 1988-07-23 | 1990-02-01 | Wella Ag | Verwendung von 2,6-dinitro-phenol-derivaten in haarfaerbemitteln |
US5312952A (en) * | 1992-04-23 | 1994-05-17 | Uniroyal Chemical Company, Inc. | Polymerization inhibitor for vinyl aromatics |
US5254760A (en) * | 1992-07-29 | 1993-10-19 | Ciba-Geigy Corporation | Inhibiting polymerization of vinyl aromatic monomers |
US5332842A (en) * | 1993-05-13 | 1994-07-26 | Exxon Chemical Patents Inc. | Process for inhibiting oxidation and polymerization of furfural and its derivatives |
US6344560B1 (en) | 2000-05-03 | 2002-02-05 | Uniroyal Chemical Company, Inc. | Nitroaromatic solubilizer for nitroxyls in aromatic solvents |
US6339177B1 (en) * | 2000-05-24 | 2002-01-15 | Sea Lion Technology, Inc. | Dinitroalkyl aromatics polymerization retarders or inhibitors and methods for making and for using same |
US20060069219A1 (en) * | 2004-09-28 | 2006-03-30 | Vilan Kosover | Sulfonated phenols with nitrophenols as polymerization inhibitors |
US8098683B2 (en) * | 2004-10-06 | 2012-01-17 | Broadcom Corporation | Method and system for implementing a single weight (SW) single channel (SC) MIMO system with no insertion loss |
EP1813585A4 (en) * | 2004-11-15 | 2009-10-28 | Hakuto Kk | PROCESS FOR INHIBITING POLYMERIZATION PRODUCING COPOLYMER OF DIVINYLBENZENE AND AROMATIC VINYL COMPOUND |
US7696290B2 (en) * | 2004-12-03 | 2010-04-13 | Crompton Corporation | Aromatic sulfonic acids, amines, and nitrophenols in combination with nitroxyl radical-containing compounds or C-nitrosanilines as polymerization inhibitors |
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GB504765A (en) * | 1937-12-24 | 1939-05-01 | Standard Telephones Cables Ltd | Improvements in or relating to the stabilisation of styrene |
US2526567A (en) * | 1948-07-06 | 1950-10-17 | Dow Chemical Co | Stabilization of nuclear chlorostyrenes by 2, 6-dinitrophenols |
US2943075A (en) * | 1956-07-02 | 1960-06-28 | Dow Chemical Co | Styrene-modified rubbery compositions and stabilized with 2-nitrophenols |
US3366702A (en) * | 1965-05-03 | 1968-01-30 | Marathon Oil Co | Preparation of unsaturated hydrocarbons by pyrolysis, and related compositions |
US3420778A (en) * | 1966-07-21 | 1969-01-07 | Simplex Wire & Cable Co | Voltage stabilized liquid dielectrics |
FR2142369A5 (zh) * | 1971-06-18 | 1973-01-26 | Huels Chemische Werke Ag | |
US4051067A (en) * | 1974-01-25 | 1977-09-27 | Monsanto Company | Stabilization of unsaturated carboxylic acid esters with mixtures of polyalkyleneamines and arylenediamines |
US4105506A (en) * | 1977-02-24 | 1978-08-08 | Cosden Technology, Inc. | Polymerization inhibitor for vinyl aromatic compounds |
US4132603A (en) * | 1977-11-23 | 1979-01-02 | Cosden Technology, Inc. | Polymerization inhibitor for vinyl aromatic compounds |
BE875237R (fr) * | 1978-07-18 | 1979-07-16 | Cosden Technology | Procede pour inhiber la polymerisation de composes vinylaromatiques facilement polymerisables |
US4376221A (en) * | 1980-03-13 | 1983-03-08 | Jackisch Philip F | Stabilization of dibromostyrene |
US4457806A (en) * | 1982-06-28 | 1984-07-03 | The Sherwin-Williams Company | Process for vinyl aromatic monomer polymerization inhibition |
US4466905A (en) * | 1983-04-11 | 1984-08-21 | Cosden Technology, Inc. | Polymerization inhibition process for vinyl aromatic compounds |
US4468343A (en) * | 1983-04-11 | 1984-08-28 | Cosden Technology, Inc. | Polymerization co-inhibitors for vinyl aromatic compounds |
US4568711A (en) * | 1984-12-07 | 1986-02-04 | The Firestone Tire & Rubber Company | Synergistic additive combination for guayule rubber stabilization |
US4654451A (en) * | 1985-12-27 | 1987-03-31 | Atlantic Richfield Company | Inhibiting polymerization of vinyl aromatic monomers |
-
1986
- 1986-01-09 US US06/817,324 patent/US4664845A/en not_active Expired - Lifetime
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-
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- 1987-01-06 DE DE8787300037T patent/DE3770019D1/de not_active Expired - Fee Related
- 1987-01-06 ES ES87300037T patent/ES2022880B3/es not_active Expired - Lifetime
- 1987-01-06 ZA ZA8769A patent/ZA8769B/xx unknown
- 1987-01-06 AT AT87300037T patent/ATE63534T1/de not_active IP Right Cessation
- 1987-01-06 EP EP87300037A patent/EP0234671B1/en not_active Expired - Lifetime
- 1987-01-06 AU AU67177/87A patent/AU595571B2/en not_active Ceased
- 1987-01-07 CA CA000526832A patent/CA1275168C/en not_active Expired - Fee Related
- 1987-01-08 BR BR8700050A patent/BR8700050A/pt not_active IP Right Cessation
- 1987-01-08 CN CN87100819.XA patent/CN1004139B/zh not_active Expired
- 1987-01-08 FI FI870071A patent/FI84906C/fi not_active IP Right Cessation
- 1987-01-08 KR KR1019870000065A patent/KR910004552B1/ko not_active IP Right Cessation
- 1987-01-09 AR AR87306440A patent/AR245096A1/es active
- 1987-01-09 DK DK011387A patent/DK11387A/da not_active Application Discontinuation
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- 1987-01-09 JP JP62003094A patent/JPH01152146A/ja active Granted
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Also Published As
Publication number | Publication date |
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CA1275168C (en) | 1990-10-16 |
FI84906C (fi) | 1992-02-10 |
AU6717787A (en) | 1987-07-16 |
ATE63534T1 (de) | 1991-06-15 |
FI870071A0 (fi) | 1987-01-08 |
AU595571B2 (en) | 1990-04-05 |
US4664845A (en) | 1987-05-12 |
FI84906B (fi) | 1991-10-31 |
JPH01152146A (ja) | 1989-06-14 |
FI870071A (fi) | 1987-07-10 |
DK11387D0 (da) | 1987-01-09 |
JPH0588699B2 (zh) | 1993-12-24 |
AR245096A1 (es) | 1993-12-30 |
KR870007227A (ko) | 1987-08-17 |
MX165080B (es) | 1992-10-21 |
EP0234671B1 (en) | 1991-05-15 |
CN87100819A (zh) | 1987-09-23 |
PT84086A (en) | 1987-02-01 |
KR910004552B1 (ko) | 1991-07-06 |
ZA8769B (en) | 1987-08-26 |
DE3770019D1 (de) | 1991-06-20 |
DK11387A (da) | 1987-07-10 |
IN166453B (zh) | 1990-05-12 |
EP0234671A1 (en) | 1987-09-02 |
ES2022880B3 (es) | 1991-12-16 |
PT84086B (pt) | 1989-02-28 |
BR8700050A (pt) | 1987-12-01 |
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