JP5683692B2 - ビニル芳香族モノマーの重合を抑制する方法及び組成物 - Google Patents
ビニル芳香族モノマーの重合を抑制する方法及び組成物 Download PDFInfo
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- JP5683692B2 JP5683692B2 JP2013513183A JP2013513183A JP5683692B2 JP 5683692 B2 JP5683692 B2 JP 5683692B2 JP 2013513183 A JP2013513183 A JP 2013513183A JP 2013513183 A JP2013513183 A JP 2013513183A JP 5683692 B2 JP5683692 B2 JP 5683692B2
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- vinyl aromatic
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- 239000000178 monomer Substances 0.000 title claims description 47
- 238000006116 polymerization reaction Methods 0.000 title claims description 35
- 229920002554 vinyl polymer Polymers 0.000 title claims description 29
- 238000000034 method Methods 0.000 title claims description 28
- 239000000203 mixture Substances 0.000 title claims description 25
- 230000002401 inhibitory effect Effects 0.000 title claims description 13
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical group C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 42
- -1 quinone methide derivative Chemical class 0.000 claims description 23
- AZQWKYJCGOJGHM-UHFFFAOYSA-N para-benzoquinone Natural products O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 21
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 239000007788 liquid Substances 0.000 claims description 9
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 claims description 5
- 239000012535 impurity Substances 0.000 claims description 5
- 150000002989 phenols Chemical class 0.000 claims description 5
- HCUWXYBKPSKTAB-UHFFFAOYSA-N 4-benzylidene-2,6-ditert-butylcyclohexa-2,5-dien-1-one Chemical compound C1=C(C(C)(C)C)C(=O)C(C(C)(C)C)=CC1=CC1=CC=CC=C1 HCUWXYBKPSKTAB-UHFFFAOYSA-N 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- 230000002265 prevention Effects 0.000 claims 3
- 238000010438 heat treatment Methods 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 7
- 239000003112 inhibitor Substances 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 6
- 239000004793 Polystyrene Substances 0.000 description 5
- 229920002223 polystyrene Polymers 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 238000012719 thermal polymerization Methods 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 2
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 2
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 2
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- UOCJDOLVGGIYIQ-PBFPGSCMSA-N cefatrizine Chemical group S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)[C@H](N)C=2C=CC(O)=CC=2)CC=1CSC=1C=NNN=1 UOCJDOLVGGIYIQ-PBFPGSCMSA-N 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 239000000806 elastomer Substances 0.000 description 2
- 230000001965 increasing effect Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 description 1
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 1
- METWAQRCMRWDAW-UHFFFAOYSA-N 2,6-diethylphenol Chemical compound CCC1=CC=CC(CC)=C1O METWAQRCMRWDAW-UHFFFAOYSA-N 0.000 description 1
- NAILKKRDWBJCNH-UHFFFAOYSA-N 2,6-dipropylphenol Chemical compound CCCC1=CC=CC(CCC)=C1O NAILKKRDWBJCNH-UHFFFAOYSA-N 0.000 description 1
- VMZVBRIIHDRYGK-UHFFFAOYSA-N 2,6-ditert-butyl-4-[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 VMZVBRIIHDRYGK-UHFFFAOYSA-N 0.000 description 1
- AKNMPWVTPUHKCG-UHFFFAOYSA-N 2-cyclohexyl-6-[(3-cyclohexyl-2-hydroxy-5-methylphenyl)methyl]-4-methylphenol Chemical compound OC=1C(C2CCCCC2)=CC(C)=CC=1CC(C=1O)=CC(C)=CC=1C1CCCCC1 AKNMPWVTPUHKCG-UHFFFAOYSA-N 0.000 description 1
- YFHKLSPMRRWLKI-UHFFFAOYSA-N 2-tert-butyl-4-(3-tert-butyl-4-hydroxy-5-methylphenyl)sulfanyl-6-methylphenol Chemical compound CC(C)(C)C1=C(O)C(C)=CC(SC=2C=C(C(O)=C(C)C=2)C(C)(C)C)=C1 YFHKLSPMRRWLKI-UHFFFAOYSA-N 0.000 description 1
- GPNYZBKIGXGYNU-UHFFFAOYSA-N 2-tert-butyl-6-[(3-tert-butyl-5-ethyl-2-hydroxyphenyl)methyl]-4-ethylphenol Chemical compound CC(C)(C)C1=CC(CC)=CC(CC=2C(=C(C=C(CC)C=2)C(C)(C)C)O)=C1O GPNYZBKIGXGYNU-UHFFFAOYSA-N 0.000 description 1
- MDWVSAYEQPLWMX-UHFFFAOYSA-N 4,4'-Methylenebis(2,6-di-tert-butylphenol) Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 MDWVSAYEQPLWMX-UHFFFAOYSA-N 0.000 description 1
- BFZOTKYPSZSDEV-GFCCVEGCSA-N 4-[(2R)-butan-2-yl]-2,6-ditert-butylphenol Chemical compound CC[C@@H](C)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 BFZOTKYPSZSDEV-GFCCVEGCSA-N 0.000 description 1
- VSAWBBYYMBQKIK-UHFFFAOYSA-N 4-[[3,5-bis[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-2,4,6-trimethylphenyl]methyl]-2,6-ditert-butylphenol Chemical compound CC1=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C1CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 VSAWBBYYMBQKIK-UHFFFAOYSA-N 0.000 description 1
- MQVDCVRWVSDQNN-UHFFFAOYSA-N 4-methyl-2-(1-methylcyclohexyl)phenol Chemical compound CC1=CC=C(O)C(C2(C)CCCCC2)=C1 MQVDCVRWVSDQNN-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
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- YMOONIIMQBGTDU-VOTSOKGWSA-N [(e)-2-bromoethenyl]benzene Chemical compound Br\C=C\C1=CC=CC=C1 YMOONIIMQBGTDU-VOTSOKGWSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000004035 construction material Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- LGRLWUINFJPLSH-UHFFFAOYSA-N methanide Chemical compound [CH3-] LGRLWUINFJPLSH-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/20—Use of additives, e.g. for stabilisation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F12/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F12/02—Monomers containing only one unsaturated aliphatic radical
- C08F12/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F12/06—Hydrocarbons
- C08F12/08—Styrene
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerisation Methods In General (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
ール)、3−(3’,5’−ジ−t−ブチル−4’−ヒドロキシフェニル)プロピオン酸
オクタデシル、4,4’−メチレンビス(2,6−ジ−t−ブチルフェノール)、1,3
,5−トリメチル−2,4,6−トリス(3,5−ジ−t−ブチル−4−ヒドロキシベンジル)ベンゼン、2,6−ジ−t−ブチル−α−ジメチルアミノ−p−クレゾール、2,6−ジ−t−ブチル−4−s−ブチルフェノール、2,2’−メチレンビス(4−エチル
−6−t−ブチルフェノール)、2,2’−メチレンビス(4−メチル−6−t−ブチル
フェノール)、2,2’−メチレンビス(6−(1−メチルシクロヘキシル)−p−クレ
ゾール及び2,2’−メチレンビス(4−メチル−6−シクロヘキシルフェノール)が挙
げられる。
Claims (16)
- ビニル芳香族モノマーの重合を抑制する方法であって、
(A)次式のキノンメチド誘導体
(B)次式のフェノール化合物
を含有する有効な重合抑制量の組成物をビニル芳香族モノマーに添加する工程
を含む方法。 - A/Bの重量比が90/10〜10/90である、請求項1記載の方法。
- 前記キノンメチド誘導体(A)が2,6−ジ−t−ブチル−4−ベンジリデンシクロヘキサ−2,5−ジエノンである、請求項2記載の方法。
- 前記フェノール化合物(B)が2,6−ジ−t−ブチルフェノールである、請求項3記載の方法。
- ビニル芳香族モノマーを基準にして合計1〜10000ppmの(A)及び(B)をビニル芳香族モノマーに接触させる、請求項4記載の方法。
- ビニル芳香族モノマーがスチレンモノマーを含む、請求項5記載の方法。
- A/Bの重量比が70/30である、請求項5記載の方法。
- さらに、スチレンモノマーを加熱する工程を含む、請求項7記載の方法。
- さらに、スチレンモノマーを蒸留して不純物を除去する工程を含む、請求項7記載の方法。
- ビニル芳香族モノマー重合防止組成物であって、液体担体と、該液体担体に溶解又は分散した
(A)次式のキノンメチド誘導体
(B)次式のフェノール化合物
を含有するビニル芳香族モノマー重合防止組成物。 - (A)及び(B)が重量比90/10〜10/90で存在する、請求項10記載のビニル芳香族モノマー重合防止組成物。
- (A)キノンメチド誘導体が2,6−ジ−t−ブチル−4−ベンジリデンシクロヘキサ−2,5−ジエノンである、請求項11記載のビニル芳香族モノマー重合防止組成物。
- (B)フェノール化合物が2,6−ジ−t−ブチルフェノールである、請求項12記載のビニル芳香族モノマー重合防止組成物。
- 液体担体が非極性有機溶剤を含み、(A)及び(B)の両方が前記溶剤に溶解している、請求項12記載のビニル芳香族モノマー重合防止組成物。
- 非極性有機溶剤が重質芳香族ナフサ又はキシレンを含む、請求項14記載のビニル芳香族モノマー重合防止組成物。
- さらに、スチレンモノマーを含有する、請求項10記載のビニル芳香族モノマー重合防止組成物。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US12/793,226 US8298440B2 (en) | 2010-06-03 | 2010-06-03 | Methods and compositions for inhibiting vinyl aromatic monomer polymerization |
US12/793,226 | 2010-06-03 | ||
PCT/US2011/035934 WO2011152961A2 (en) | 2010-06-03 | 2011-05-10 | Methods and compositions for inhibiting vinyl aromatic monomer polymerization |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2013539473A JP2013539473A (ja) | 2013-10-24 |
JP2013539473A5 JP2013539473A5 (ja) | 2014-06-26 |
JP5683692B2 true JP5683692B2 (ja) | 2015-03-11 |
Family
ID=44626629
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2013513183A Active JP5683692B2 (ja) | 2010-06-03 | 2011-05-10 | ビニル芳香族モノマーの重合を抑制する方法及び組成物 |
Country Status (14)
Country | Link |
---|---|
US (2) | US8298440B2 (ja) |
EP (1) | EP2576718B1 (ja) |
JP (1) | JP5683692B2 (ja) |
KR (1) | KR101877069B1 (ja) |
AR (1) | AR081555A1 (ja) |
BR (1) | BR112012028981B1 (ja) |
CA (1) | CA2800495C (ja) |
ES (1) | ES2621605T3 (ja) |
MX (1) | MX2012014075A (ja) |
MY (1) | MY158328A (ja) |
PL (1) | PL2576718T3 (ja) |
SG (1) | SG185758A1 (ja) |
TW (1) | TWI501947B (ja) |
WO (1) | WO2011152961A2 (ja) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8901362B2 (en) * | 2012-02-02 | 2014-12-02 | General Electric Company | Methods and compositions for styrene inhibition via in situ generation of quinone methides |
BR112015003564B1 (pt) | 2012-08-24 | 2021-01-05 | Dorf Ketal Chemicals (I) Private Limited | composto aditivo para o controle e inibição da polimerização de monômeros vinil aromáticos incluindo estireno, uso do composto e seu método de preparação e método para o controle e inibição da polimerização de monômeros vinil aromáticos incluindo estireno |
EP2958949A1 (en) * | 2013-02-19 | 2015-12-30 | General Electric Company | Use of aliphatic nitroso compounds as inhibitors of radical polymerization of activated vinyl monomers |
MY185850A (en) * | 2016-02-13 | 2021-06-14 | Dorf Ketal Chemicals India Private Ltd | Compositions for control and inhibition of polymerization of vinyl aromatic monomers, and methods of use thereof |
CN109651040A (zh) * | 2017-10-12 | 2019-04-19 | 中国石油化工股份有限公司 | 高级炔烃复配阻聚剂 |
CN110878209A (zh) * | 2018-09-05 | 2020-03-13 | 中国石油化工股份有限公司 | 用于苯乙烯精馏系统的环保阻聚剂及其应用 |
CN116553996A (zh) * | 2023-07-07 | 2023-08-08 | 吉林金海化工新材料有限公司 | 一种阻聚剂及其应用 |
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US3741906A (en) * | 1971-12-17 | 1973-06-26 | Exxon Research Engineering Co | Hindered phenoxy radicals |
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EP0744392A1 (en) * | 1995-05-26 | 1996-11-27 | Ciba-Geigy Ag | A new one-pot process for the preparation of 7-aryl-2,6-disubstituted quinone methides |
JPH09227608A (ja) * | 1996-02-22 | 1997-09-02 | Asahi Chem Ind Co Ltd | スチレンーアクリロニトリル系樹脂の製造方法 |
KR20000068400A (ko) * | 1996-09-04 | 2000-11-25 | 그래햄 이. 테일러 | 폴리올레핀에 유리 라디칼 억제제를 혼입하여 열화를 억제하는방법 |
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JP2004352735A (ja) * | 2003-05-27 | 2004-12-16 | Techno Network Shikoku Co Ltd | ラジカル重合体の製造方法 |
US7128826B2 (en) | 2003-07-31 | 2006-10-31 | General Electric Company | Polymerization inhibitor for styrene dehydrogenation units |
DE102007052891A1 (de) * | 2007-11-02 | 2009-05-07 | Evonik Degussa Gmbh | Verfahren zur Stabilisierung von olefinisch ungesättigten Monomeren |
JP5139103B2 (ja) * | 2008-02-05 | 2013-02-06 | 京セラドキュメントソリューションズ株式会社 | 電子写真感光体及び画像形成装置 |
JP5266991B2 (ja) * | 2008-09-11 | 2013-08-21 | コニカミノルタビジネステクノロジーズ株式会社 | 電子写真感光体とそれを用いた画像形成装置 |
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WO2011152961A3 (en) | 2013-08-22 |
KR101877069B1 (ko) | 2018-07-10 |
BR112012028981B1 (pt) | 2020-10-20 |
TWI501947B (zh) | 2015-10-01 |
BR112012028981A2 (pt) | 2016-07-26 |
US8298440B2 (en) | 2012-10-30 |
PL2576718T3 (pl) | 2017-11-30 |
SG185758A1 (en) | 2012-12-28 |
EP2576718A2 (en) | 2013-04-10 |
JP2013539473A (ja) | 2013-10-24 |
MY158328A (en) | 2016-09-30 |
US20130030225A1 (en) | 2013-01-31 |
EP2576718B1 (en) | 2017-01-11 |
WO2011152961A2 (en) | 2011-12-08 |
TW201202192A (en) | 2012-01-16 |
US20110297878A1 (en) | 2011-12-08 |
CA2800495C (en) | 2019-07-09 |
AR081555A1 (es) | 2012-10-03 |
CA2800495A1 (en) | 2011-12-08 |
MX2012014075A (es) | 2013-01-25 |
ES2621605T3 (es) | 2017-07-04 |
KR20130122517A (ko) | 2013-11-07 |
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