KR20050059308A - 폴리우레탄 분산액 및 이로부터 제조된 제품 - Google Patents
폴리우레탄 분산액 및 이로부터 제조된 제품 Download PDFInfo
- Publication number
- KR20050059308A KR20050059308A KR1020057007223A KR20057007223A KR20050059308A KR 20050059308 A KR20050059308 A KR 20050059308A KR 1020057007223 A KR1020057007223 A KR 1020057007223A KR 20057007223 A KR20057007223 A KR 20057007223A KR 20050059308 A KR20050059308 A KR 20050059308A
- Authority
- KR
- South Korea
- Prior art keywords
- bis
- cyclohexane
- isocyanatomethyl
- polyurethane dispersion
- polyurethane
- Prior art date
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- 229920003009 polyurethane dispersion Polymers 0.000 title claims abstract description 38
- 239000006185 dispersion Substances 0.000 claims abstract description 49
- 239000000203 mixture Substances 0.000 claims abstract description 48
- ROHUXHMNZLHBSF-UHFFFAOYSA-N 1,4-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1CCC(CN=C=O)CC1 ROHUXHMNZLHBSF-UHFFFAOYSA-N 0.000 claims abstract description 26
- XSCLFFBWRKTMTE-AOOOYVTPSA-N (1r,3s)-1,3-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NC[C@H]1CCC[C@@H](CN=C=O)C1 XSCLFFBWRKTMTE-AOOOYVTPSA-N 0.000 claims abstract description 5
- QXRRAZIZHCWBQY-UHFFFAOYSA-N 1,1-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1(CN=C=O)CCCCC1 QXRRAZIZHCWBQY-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229920005862 polyol Polymers 0.000 claims description 47
- 150000003077 polyols Chemical class 0.000 claims description 44
- 239000004970 Chain extender Substances 0.000 claims description 31
- 229920002635 polyurethane Polymers 0.000 claims description 27
- 239000004814 polyurethane Substances 0.000 claims description 27
- 239000004094 surface-active agent Substances 0.000 claims description 23
- -1 bis (isocyanatomethyl) cyclohexane compound Chemical class 0.000 claims description 21
- 239000005056 polyisocyanate Substances 0.000 claims description 17
- 229920001228 polyisocyanate Polymers 0.000 claims description 17
- 229920001971 elastomer Polymers 0.000 claims description 12
- 239000000806 elastomer Substances 0.000 claims description 12
- 239000006260 foam Substances 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000007787 solid Substances 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 238000000576 coating method Methods 0.000 claims description 9
- 229920000570 polyether Polymers 0.000 claims description 5
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 229920000728 polyester Polymers 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 3
- 229920000515 polycarbonate Polymers 0.000 claims description 3
- 239000004417 polycarbonate Substances 0.000 claims description 3
- 229920005903 polyol mixture Polymers 0.000 claims description 3
- XZAHJRZBUWYCBM-UHFFFAOYSA-N [1-(aminomethyl)cyclohexyl]methanamine Chemical compound NCC1(CN)CCCCC1 XZAHJRZBUWYCBM-UHFFFAOYSA-N 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 125000002091 cationic group Chemical group 0.000 claims description 2
- 229920000098 polyolefin Polymers 0.000 claims description 2
- 239000012736 aqueous medium Substances 0.000 claims 2
- 125000000129 anionic group Chemical group 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 229920000768 polyamine Polymers 0.000 claims 1
- 239000012948 isocyanate Substances 0.000 abstract description 35
- 150000002513 isocyanates Chemical class 0.000 abstract description 35
- 229920001730 Moisture cure polyurethane Polymers 0.000 abstract description 15
- 238000006243 chemical reaction Methods 0.000 abstract description 10
- XSCLFFBWRKTMTE-UWVGGRQHSA-N (1s,3s)-1,3-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NC[C@H]1CCC[C@H](CN=C=O)C1 XSCLFFBWRKTMTE-UWVGGRQHSA-N 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- 229920000642 polymer Polymers 0.000 description 20
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 18
- 239000010408 film Substances 0.000 description 16
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 description 16
- 238000000034 method Methods 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 15
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- 150000001412 amines Chemical class 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
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- 150000001875 compounds Chemical class 0.000 description 8
- 150000002009 diols Chemical class 0.000 description 8
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 239000004971 Cross linker Substances 0.000 description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000005058 Isophorone diisocyanate Substances 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 6
- 239000002245 particle Substances 0.000 description 6
- 239000002562 thickening agent Substances 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 239000004816 latex Substances 0.000 description 5
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- 150000003839 salts Chemical class 0.000 description 5
- 239000004809 Teflon Substances 0.000 description 4
- 229920006362 Teflon® Polymers 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- OXIKYYJDTWKERT-UHFFFAOYSA-N [4-(aminomethyl)cyclohexyl]methanamine Chemical compound NCC1CCC(CN)CC1 OXIKYYJDTWKERT-UHFFFAOYSA-N 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 125000005442 diisocyanate group Chemical group 0.000 description 4
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 4
- 239000003999 initiator Substances 0.000 description 4
- 229920005906 polyester polyol Polymers 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 3
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
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- 239000003139 biocide Substances 0.000 description 3
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- 150000004985 diamines Chemical class 0.000 description 3
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- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
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- PSGAAPLEWMOORI-PEINSRQWSA-N medroxyprogesterone acetate Chemical compound C([C@@]12C)CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2CC[C@]2(C)[C@@](OC(C)=O)(C(C)=O)CC[C@H]21 PSGAAPLEWMOORI-PEINSRQWSA-N 0.000 description 3
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- 229920001223 polyethylene glycol Polymers 0.000 description 3
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- UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 2
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- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
- C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
- C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
- C08G18/757—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing at least two isocyanate or isothiocyanate groups linked to the cycloaliphatic ring by means of an aliphatic group
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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Abstract
Description
Claims (15)
- 수소 활성 잔기를 갖는 분자와 비스(이소시아네이토메틸)사이클로헥산 화합물을 포함하는 폴리이소시아네이트와의 혼합물과 임의로 연쇄 연장제 및/또는 계면활성제를 포함하는, 폴리우레탄 분산액.
- 제1항에 있어서, 폴리이소시아네이트가 트랜스-1,4-비스(이소시아네이토메틸)사이클로헥산(i) 또는 시스-1,3-비스(이소시아네이토메틸)사이클로헥산, 트랜스-1,3-비스(이소시아네이토메틸)사이클로헥산, 시스-1,4-비스(이소시아네이토메틸)사이클로헥산 및 트랜스-1,4-비스(이소시아네이토메틸)사이클로헥산 중의 둘 이상의 이성체성 혼합물(ii)을 포함하고, 당해 이성체성 혼합물이 트랜스-1,4-비스(이소시아네이토메틸)사이클로헥산을 약 5중량% 이상 포함하는, 폴리우레탄 분산액.
- 제2항에 있어서, 폴리우레탄이 수성 매질 속에 분산되어 있는, 폴리우레탄 분산액.
- 제3항에 있어서, 수성 매질이 잔류 유기 용매를 5% 미만 포함하는, 폴리우레탄 분산액.
- 제1항에 있어서, 수소 활성 잔기를 갖는 분자가, 중량 평균 분자량이 300 내지 10,000이고 평균 관능가가 1.8 내지 4.5인 폴리올 또는 폴리올 혼합물인, 폴리우레탄 분산액.
- 제5항에 있어서, 폴리올이 폴리에스테르, 폴리에테르, 폴리락톤, 폴리올레핀, 폴리카보네이트 및 이들의 혼합물로부터 선택된 지방족 또는 방향족 폴리올인, 폴리우레탄 분산액.
- 제1항에 있어서, 폴리아민 연쇄 연장제를 포함하는, 폴리우레탄 분산액.
- 제7항에 있어서, 연쇄 연장제가 피페라진, 에틸렌디아민 및 비스(아미노메틸)사이클로헥산으로부터 선택되는, 폴리우레탄 분산액.
- 제1항에 있어서, 고체를 30 내지 75중량% 포함하는, 폴리우레탄 분산액.
- 제1항에 있어서, 음이온성, 이온성, 양이온성 또는 쯔비터이온성 외부 계면활성제를 포함하는, 폴리우레탄 분산액.
- 제1항에 있어서, 내부 계면활성제에 의해 안정화되는, 폴리우레탄 분산액.
- 수소 활성 잔기를 갖는 분자와 비스(이소시아네이토메틸)사이클로헥산 화합물을 포함하는 폴리이소시아네이트와의 혼합물과 임의로 연쇄 연장제 및/또는 계면활성제를 포함하는 폴리우레탄 분산액의 제조방법.
- 제1항에 따르는 분산액으로부터 제조된 피막, 필름, 엘라스토머 또는 미세 발포체.
- 제1항에 따르는 분산액으로부터 제조된 자외선 또는 일광 안정성 피막, 필름 또는 엘라스토머.
- 제2항에 있어서, 폴리이소시아네이트가 비스(이소시아네이토메틸)사이클로헥산 이외의 하나 이상의 폴리이소시아네이트를 0.1 내지 20중량% 포함하는 분산액.
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PCT/US2003/034196 WO2004041890A1 (en) | 2002-10-31 | 2003-10-28 | Polyurethane dispersion and articles prepared therefrom |
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US (1) | US7232859B2 (ko) |
EP (1) | EP1558659B1 (ko) |
JP (2) | JP2006504849A (ko) |
KR (1) | KR101111990B1 (ko) |
CN (1) | CN100564419C (ko) |
AU (1) | AU2003284196A1 (ko) |
BR (1) | BR0315067B1 (ko) |
CA (1) | CA2504147C (ko) |
MX (1) | MXPA05004674A (ko) |
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KR20190041018A (ko) * | 2016-11-17 | 2019-04-19 | 미쓰이 가가쿠 가부시키가이샤 | 발포용 열가소성 폴리유레테인 수지 및 그의 제조 방법, 및 성형품 |
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- 2003-10-28 KR KR1020057007223A patent/KR101111990B1/ko active IP Right Grant
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- 2003-10-28 CN CNB2003801025186A patent/CN100564419C/zh not_active Expired - Lifetime
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KR101503098B1 (ko) * | 2007-11-16 | 2015-03-16 | 미쓰이 가가쿠 가부시키가이샤 | 수성 폴리우레탄 수지, 도막, 인공 또는 합성 피혁 |
KR20190041018A (ko) * | 2016-11-17 | 2019-04-19 | 미쓰이 가가쿠 가부시키가이샤 | 발포용 열가소성 폴리유레테인 수지 및 그의 제조 방법, 및 성형품 |
KR20210090896A (ko) * | 2020-01-13 | 2021-07-21 | 한국신발피혁연구원 | 스웨이드 함침용 폴리우레탄 분산액 |
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JP2011046968A (ja) | 2011-03-10 |
CN100564419C (zh) | 2009-12-02 |
WO2004041890A1 (en) | 2004-05-21 |
TW200418895A (en) | 2004-10-01 |
CA2504147C (en) | 2012-08-14 |
BR0315067B1 (pt) | 2014-07-29 |
BR0315067A (pt) | 2005-08-16 |
AU2003284196A1 (en) | 2004-06-07 |
US7232859B2 (en) | 2007-06-19 |
MXPA05004674A (es) | 2005-06-08 |
CN1708524A (zh) | 2005-12-14 |
WO2004041890A9 (en) | 2004-07-22 |
EP1558659A1 (en) | 2005-08-03 |
CA2504147A1 (en) | 2004-05-21 |
EP1558659B1 (en) | 2013-01-09 |
JP2006504849A (ja) | 2006-02-09 |
KR101111990B1 (ko) | 2012-02-17 |
US20060058453A1 (en) | 2006-03-16 |
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