JP2006527179A - アルキレニレングリコールの（メタ）アクリル酸エステルおよびその使用 - Google Patents

アルキレニレングリコールの（メタ）アクリル酸エステルおよびその使用 Download PDF

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Publication number: JP2006527179A
Authority: JP; Japan
Prior art keywords: reaction mixture; ester; weight; optionally; acrylic acid
Prior art date: 2003-06-06
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Pending

Application number

JP2006508273A

Other languages

English (en)

Japanese (ja)

Inventor

リーゲルウルリヒ

トーマス　ダニエル

ヴァイスマンテルマティーアス

エリオットマルク

フンクリューディガー

ラインホルト　シュヴァルム

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

BASF SE

Original Assignee

BASF SE

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2003-06-06

Filing date

2004-06-04

Publication date

2006-11-30

2003-06-06 Priority claimed from PCT/EP2003/005953 external-priority patent/WO2003104300A1/fr

2003-12-11 Priority claimed from DE2003158369 external-priority patent/DE10358369A1/de

2004-06-04 Application filed by BASF SE filed Critical BASF SE

2006-11-30 Publication of JP2006527179A publication Critical patent/JP2006527179A/ja

Status Pending legal-status Critical Current

Links

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WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 title claims abstract description 19
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 title claims description 49
239000011541 reaction mixture Substances 0.000 claims abstract description 75
150000002148 esters Chemical class 0.000 claims abstract description 55
150000001875 compounds Chemical class 0.000 claims abstract description 14
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims abstract description 3
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XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 71
238000000034 method Methods 0.000 claims description 70
238000006243 chemical reaction Methods 0.000 claims description 43
238000005886 esterification reaction Methods 0.000 claims description 42
230000032050 esterification Effects 0.000 claims description 41
239000002253 acid Substances 0.000 claims description 40
239000007788 liquid Substances 0.000 claims description 40
239000002904 solvent Substances 0.000 claims description 40
239000004971 Cross linker Substances 0.000 claims description 38
239000003431 cross linking reagent Substances 0.000 claims description 32
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238000006116 polymerization reaction Methods 0.000 claims description 28
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238000001035 drying Methods 0.000 claims description 20
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239000007789 gas Substances 0.000 description 13
NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 13
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244000269722 Thea sinensis Species 0.000 description 8
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 8
239000003795 chemical substances by application Substances 0.000 description 8
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VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 8
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VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 7
ICKWICRCANNIBI-UHFFFAOYSA-N 2,4-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C(C(C)(C)C)=C1 ICKWICRCANNIBI-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
206010021639 Incontinence Diseases 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
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TVZISJTYELEYPI-UHFFFAOYSA-N hypodiphosphoric acid Chemical compound OP(O)(=O)P(O)(O)=O TVZISJTYELEYPI-UHFFFAOYSA-N 0.000 description 6
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 6
239000011976 maleic acid Substances 0.000 description 6
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238000005259 measurement Methods 0.000 description 6
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HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 4
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FSWDLYNGJBGFJH-UHFFFAOYSA-N n,n'-di-2-butyl-1,4-phenylenediamine Chemical compound CCC(C)NC1=CC=C(NC(C)CC)C=C1 FSWDLYNGJBGFJH-UHFFFAOYSA-N 0.000 description 1
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239000003505 polymerization initiator Substances 0.000 description 1
229920000193 polymethacrylate Polymers 0.000 description 1
229920005650 polypropylene glycol diacrylate Polymers 0.000 description 1
229920000166 polytrimethylene carbonate Polymers 0.000 description 1
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239000004814 polyurethane Substances 0.000 description 1
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235000015497 potassium bicarbonate Nutrition 0.000 description 1
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235000011181 potassium carbonates Nutrition 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
244000144977 poultry Species 0.000 description 1
235000013594 poultry meat Nutrition 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
230000002028 premature Effects 0.000 description 1
150000003138 primary alcohols Chemical class 0.000 description 1
UIIIBRHUICCMAI-UHFFFAOYSA-N prop-2-ene-1-sulfonic acid Chemical compound OS(=O)(=O)CC=C UIIIBRHUICCMAI-UHFFFAOYSA-N 0.000 description 1
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238000011403 purification operation Methods 0.000 description 1
238000011002 quantification Methods 0.000 description 1
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239000000376 reactant Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
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230000000552 rheumatic effect Effects 0.000 description 1
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239000000377 silicon dioxide Substances 0.000 description 1
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235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
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235000011152 sodium sulphate Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
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239000000600 sorbitol Substances 0.000 description 1
238000005728 strengthening Methods 0.000 description 1
150000003440 styrenes Chemical class 0.000 description 1
BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 description 1
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230000002194 synthesizing effect Effects 0.000 description 1
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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 description 1
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
238000012360 testing method Methods 0.000 description 1
DGQOCLATAPFASR-UHFFFAOYSA-N tetrahydroxy-1,4-benzoquinone Chemical compound OC1=C(O)C(=O)C(O)=C(O)C1=O DGQOCLATAPFASR-UHFFFAOYSA-N 0.000 description 1
229920002397 thermoplastic olefin Polymers 0.000 description 1
229920005992 thermoplastic resin Polymers 0.000 description 1
150000003585 thioureas Chemical class 0.000 description 1
238000004448 titration Methods 0.000 description 1
229930003799 tocopherol Natural products 0.000 description 1
239000011732 tocopherol Substances 0.000 description 1
235000010384 tocopherol Nutrition 0.000 description 1
229960001295 tocopherol Drugs 0.000 description 1
238000012549 training Methods 0.000 description 1
GTZCVFVGUGFEME-UHFFFAOYSA-N trans-aconitic acid Natural products OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 0.000 description 1
LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
BJIOGJUNALELMI-UHFFFAOYSA-N trans-isoeugenol Natural products COC1=CC(C=CC)=CC=C1O BJIOGJUNALELMI-UHFFFAOYSA-N 0.000 description 1
238000005809 transesterification reaction Methods 0.000 description 1
230000007704 transition Effects 0.000 description 1
VPYJNCGUESNPMV-UHFFFAOYSA-N triallylamine Chemical compound C=CCN(CC=C)CC=C VPYJNCGUESNPMV-UHFFFAOYSA-N 0.000 description 1
BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
PZSJOBKRSVRODF-UHFFFAOYSA-N vanillin acetate Chemical compound COC1=CC(C=O)=CC=C1OC(C)=O PZSJOBKRSVRODF-UHFFFAOYSA-N 0.000 description 1
229920001567 vinyl ester resin Polymers 0.000 description 1
NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
239000011709 vitamin E Substances 0.000 description 1
235000019165 vitamin E Nutrition 0.000 description 1
229940046009 vitamin E Drugs 0.000 description 1
239000007762 w/o emulsion Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1
210000002268 wool Anatomy 0.000 description 1
239000008096 xylene Substances 0.000 description 1
239000010457 zeolite Substances 0.000 description 1
229910001928 zirconium oxide Inorganic materials 0.000 description 1
239000011590 β-tocopherol Substances 0.000 description 1
235000007680 β-tocopherol Nutrition 0.000 description 1
FGYKUFVNYVMTAM-WAZJVIJMSA-N β-tocotrienol Chemical compound OC1=CC(C)=C2O[C@@](CC/C=C(C)/CC/C=C(C)/CCC=C(C)C)(C)CCC2=C1C FGYKUFVNYVMTAM-WAZJVIJMSA-N 0.000 description 1
239000002478 γ-tocopherol Substances 0.000 description 1
239000002446 δ-tocopherol Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/331—Polymers modified by chemical after-treatment with organic compounds containing oxygen
- C08G65/332—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof
- C08G65/3322—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof acyclic
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
- C08G65/2606—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups
- C08G65/2609—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups containing aliphatic hydroxyl groups

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Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
General Chemical & Material Sciences (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Macromonomer-Based Addition Polymer (AREA)
Polyethers (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

JP2006508273A 2003-06-06 2004-06-04 アルキレニレングリコールの（メタ）アクリル酸エステルおよびその使用 Pending JP2006527179A (ja)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
PCT/EP2003/005953 WO2003104300A1 (fr)	2002-06-01	2003-06-06	Esters (meth)acryliques de trimethylolpropane polyalcoxyle
DE2003158369 DE10358369A1 (de)	2003-06-06	2003-12-11	(Meth)acrylester von Alkylenylenglycolen und deren Verwendung
PCT/EP2004/006033 WO2004108795A1 (fr)	2003-06-06	2004-06-04	Esters (meth)acryliques de glycols alkylene-ylene et leur utilisation

Publications (1)

Publication Number	Publication Date
JP2006527179A true JP2006527179A (ja)	2006-11-30

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JP2006508273A Pending JP2006527179A (ja)	2003-06-06	2004-06-04	アルキレニレングリコールの（メタ）アクリル酸エステルおよびその使用

Country Status (6)

Country	Link
EP (1)	EP1636291A1 (fr)
JP (1)	JP2006527179A (fr)
BR (1)	BRPI0410899A (fr)
CA (1)	CA2527362A1 (fr)
MX (1)	MXPA05012802A (fr)
WO (1)	WO2004108795A1 (fr)

Cited By (3)

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Publication number	Priority date	Publication date	Assignee	Title
JP2009529477A (ja) *	2006-03-14	2009-08-20	ビーエーエスエフソシエタス・ヨーロピア	吸水性ポリマー粒子を空気により搬送する方法
JP2011526961A (ja) *	2008-07-07	2011-10-20	エボニックレームゲゼルシャフトミットベシュレンクテルハフツング	ポリアルキレングリコールジ（メタ）アクリレートの製造方法
JP2022544708A (ja) *	2019-09-19	2022-10-20	エルジー・ケム・リミテッド	エステル化生成物の中和／水分離槽及びエステル化生成物の中和／水分離方法

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CN100528940C (zh) *	2004-03-30	2009-08-19	巴斯福股份公司	制备超吸收性聚合物的改进方法
DE102005002412A1 (de) *	2005-01-18	2006-07-27	Basf Ag	Verfahren zur Herstellung von Polymeren durch Sprühpolymerisation
DE102006008998A1 (de)	2006-02-23	2007-08-30	Röhm Gmbh	Verfahren zur Herstellung von Alkoxypolyoxyalkylen(meth)acrylaten
EP1996493A2 (fr)	2006-03-14	2008-12-03	Basf Se	Procédé pour transporter de manière pneumatique des particules polymères absorbant l'eau
DE102006039420A1 (de)	2006-08-23	2008-02-28	Evonik Rohmax Additves Gmbh	Verfahren zur Herstellung von Methacrylatestern
EP2197833A1 (fr) *	2007-09-21	2010-06-23	DSM IP Assets B.V.	Acrylate de polyesteramine ramifie
KR102429543B1 (ko) *	2018-10-18	2022-08-04	주식회사 엘지화학	신규한 가교제 화합물 및 이를 이용하여 제조되는 고흡수성 수지
CN112661638B (zh) *	2020-12-18	2022-07-15	宁波坚锋新材料有限公司	一种增韧中间体及其制备方法以及用于3d打印的增韧驱蚊高分子生物降解复合材料

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JPH069717A (ja) *	1992-03-05	1994-01-18	Nippon Shokubai Co Ltd	吸水性樹脂の製造方法
JPH09147412A (ja) *	1995-11-22	1997-06-06	Tomoegawa Paper Co Ltd	可逆性記録媒体
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CN1250622C (zh) *	2001-01-19	2006-04-12	巴斯福股份公司	吸水剂、其制备方法及其应用
EP1270530A1 (fr) *	2001-06-20	2003-01-02	Cognis Iberia, S.L.	Retardateur de prise pour plâtre

2004
- 2004-06-04 WO PCT/EP2004/006033 patent/WO2004108795A1/fr active Application Filing
- 2004-06-04 MX MXPA05012802A patent/MXPA05012802A/es unknown
- 2004-06-04 JP JP2006508273A patent/JP2006527179A/ja active Pending
- 2004-06-04 BR BRPI0410899-0A patent/BRPI0410899A/pt not_active IP Right Cessation
- 2004-06-04 EP EP04736051A patent/EP1636291A1/fr not_active Withdrawn
- 2004-06-04 CA CA002527362A patent/CA2527362A1/fr not_active Abandoned

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BRPI0410899A (pt)	2006-07-04
CA2527362A1 (fr)	2004-12-16
MXPA05012802A (es)	2006-02-22
EP1636291A1 (fr)	2006-03-22
WO2004108795A1 (fr)	2004-12-16

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KR20050019130A (ko)	2005-02-28	폴리알콕실화 글리세린의 (메트)아크릴산 에스테르

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