TWI443118B - 使用包括１，３-及１，４-環己二甲醇鏈伸長劑之混合物之低濁度熱塑性聚胺甲酸酯 - Google Patents
使用包括１，３-及１，４-環己二甲醇鏈伸長劑之混合物之低濁度熱塑性聚胺甲酸酯 Download PDFInfo
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- TWI443118B TWI443118B TW097109305A TW97109305A TWI443118B TW I443118 B TWI443118 B TW I443118B TW 097109305 A TW097109305 A TW 097109305A TW 97109305 A TW97109305 A TW 97109305A TW I443118 B TWI443118 B TW I443118B
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- Taiwan
- Prior art keywords
- cyclohexanedimethanol
- thermoplastic polyurethane
- mixture
- polyurethane elastomer
- weight
- Prior art date
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- 229920002803 thermoplastic polyurethane Polymers 0.000 title claims description 79
- 239000004433 Thermoplastic polyurethane Substances 0.000 title claims description 78
- 239000000203 mixture Substances 0.000 title claims description 70
- 239000004970 Chain extender Substances 0.000 title claims description 46
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 title claims description 16
- 229920001971 elastomer Polymers 0.000 claims description 73
- 239000000806 elastomer Substances 0.000 claims description 73
- -1 acyclic diol Chemical class 0.000 claims description 35
- 150000002009 diols Chemical class 0.000 claims description 32
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 29
- 229920000642 polymer Polymers 0.000 claims description 25
- 229920000728 polyester Polymers 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 22
- ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 claims description 19
- 125000005442 diisocyanate group Chemical group 0.000 claims description 15
- 229920000570 polyether Polymers 0.000 claims description 15
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 13
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 13
- 239000007795 chemical reaction product Substances 0.000 claims description 11
- LUSFFPXRDZKBMF-UHFFFAOYSA-N [3-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCCC(CO)C1 LUSFFPXRDZKBMF-UHFFFAOYSA-N 0.000 claims description 9
- 238000002347 injection Methods 0.000 claims description 9
- 239000007924 injection Substances 0.000 claims description 9
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 8
- 150000004985 diamines Chemical class 0.000 claims description 6
- 229920001610 polycaprolactone Polymers 0.000 claims description 5
- 238000012360 testing method Methods 0.000 claims description 5
- 239000001361 adipic acid Substances 0.000 claims description 4
- 235000011037 adipic acid Nutrition 0.000 claims description 4
- 238000001746 injection moulding Methods 0.000 claims description 4
- LUSFFPXRDZKBMF-OCAPTIKFSA-N [(1s,3r)-3-(hydroxymethyl)cyclohexyl]methanol Chemical compound OC[C@H]1CCC[C@@H](CO)C1 LUSFFPXRDZKBMF-OCAPTIKFSA-N 0.000 claims description 3
- LUSFFPXRDZKBMF-YUMQZZPRSA-N [(1s,3s)-3-(hydroxymethyl)cyclohexyl]methanol Chemical compound OC[C@H]1CCC[C@H](CO)C1 LUSFFPXRDZKBMF-YUMQZZPRSA-N 0.000 claims description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 1
- 239000000463 material Substances 0.000 description 24
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- 238000006116 polymerization reaction Methods 0.000 description 14
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 11
- 239000012948 isocyanate Substances 0.000 description 11
- 229920005862 polyol Polymers 0.000 description 11
- 230000003287 optical effect Effects 0.000 description 10
- 150000003077 polyols Chemical class 0.000 description 10
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
- 150000002513 isocyanates Chemical class 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- 239000012535 impurity Substances 0.000 description 7
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
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- 238000006243 chemical reaction Methods 0.000 description 5
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- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 229920002635 polyurethane Polymers 0.000 description 5
- 239000004814 polyurethane Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
- 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 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
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- 229920001577 copolymer Polymers 0.000 description 4
- 239000003431 cross linking reagent Substances 0.000 description 4
- PFURGBBHAOXLIO-UHFFFAOYSA-N cyclohexane-1,2-diol Chemical compound OC1CCCCC1O PFURGBBHAOXLIO-UHFFFAOYSA-N 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- 229920000620 organic polymer Polymers 0.000 description 4
- 239000008188 pellet Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 3
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- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
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- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 3
- 229920001228 polyisocyanate Polymers 0.000 description 3
- 239000005056 polyisocyanate Substances 0.000 description 3
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 2
- IPNQEKDRLAFQKQ-UHFFFAOYSA-N 1,2-dimethylcyclohexane-1,2-diol Chemical compound CC1(O)CCCCC1(C)O IPNQEKDRLAFQKQ-UHFFFAOYSA-N 0.000 description 2
- RWLALWYNXFYRGW-UHFFFAOYSA-N 2-Ethyl-1,3-hexanediol Chemical compound CCCC(O)C(CC)CO RWLALWYNXFYRGW-UHFFFAOYSA-N 0.000 description 2
- VNAWKNVDKFZFSU-UHFFFAOYSA-N 2-ethyl-2-methylpropane-1,3-diol Chemical compound CCC(C)(CO)CO VNAWKNVDKFZFSU-UHFFFAOYSA-N 0.000 description 2
- HERSWHWQXZRIDA-UHFFFAOYSA-N 3,7-dimethylocta-1,6-dien-3-amine Chemical compound CC(C)=CCCC(C)(N)C=C HERSWHWQXZRIDA-UHFFFAOYSA-N 0.000 description 2
- ALRHLSYJTWAHJZ-UHFFFAOYSA-N 3-hydroxypropionic acid Chemical compound OCCC(O)=O ALRHLSYJTWAHJZ-UHFFFAOYSA-N 0.000 description 2
- DPKWXRUINJHOOB-UHFFFAOYSA-N 4-(2-hydroxyethoxy)phenol Chemical compound OCCOC1=CC=C(O)C=C1 DPKWXRUINJHOOB-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
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- 239000004971 Cross linker Substances 0.000 description 2
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- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
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- XLJMAIOERFSOGZ-UHFFFAOYSA-N anhydrous cyanic acid Natural products OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 description 2
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- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000004427 diamine group Chemical group 0.000 description 2
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
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- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
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- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
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- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
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- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
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- DVIPPHSQIBKWSA-UHFFFAOYSA-N 4-chlorophthalic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1C(O)=O DVIPPHSQIBKWSA-UHFFFAOYSA-N 0.000 description 1
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- 229910052582 BN Inorganic materials 0.000 description 1
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 description 1
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- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
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- 150000008366 benzophenones Chemical class 0.000 description 1
- 125000003354 benzotriazolyl group Chemical class N1N=NC2=C1C=CC=C2* 0.000 description 1
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- B29K2221/003—Thermoplastic elastomers
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- 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
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Landscapes
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| US8357768B2 (en) * | 2005-12-09 | 2013-01-22 | Hani Farah | Low haze thermoplastic polyurethane using co-chain extenders |
| CN101679655A (zh) * | 2007-05-21 | 2010-03-24 | 陶氏环球技术公司 | 涂布物体 |
| US20110054056A1 (en) * | 2008-05-22 | 2011-03-03 | Hefner Jr Robert E | Thermoset polyurethanes |
| US9957346B2 (en) * | 2011-02-23 | 2018-05-01 | The University Of Akron | Melt processible polyureas and polyurea-urethanes, method for the production thereof and products made therefrom |
| IN2014DN10819A (https=) * | 2012-06-08 | 2015-09-04 | Poly Med Inc | |
| KR102171723B1 (ko) * | 2013-02-04 | 2020-10-29 | 루브리졸 어드밴스드 머티어리얼스, 인코포레이티드 | 투명한 소수성 tpu |
| WO2014210098A1 (en) * | 2013-06-27 | 2014-12-31 | Lubrizol Advanced Materials, Inc. | Fast recovery hard thermoplastic polyurethanes |
| EP2952531A1 (de) * | 2014-06-02 | 2015-12-09 | Basf Se | Kompakte Elastomerformteile auf Basis von Polyurethan |
| US10463105B2 (en) | 2014-08-27 | 2019-11-05 | Nike, Inc. | Articles of footwear, apparel, and sports equipment with soil-shedding properties |
| US10070686B2 (en) | 2014-08-27 | 2018-09-11 | Nike, Inc. | Soil-shedding article of footwear, components thereof, and methods of making the article |
| TWI706737B (zh) | 2014-08-27 | 2020-10-11 | 荷蘭商耐基創新公司 | 具污垢脫落性能之鞋類製品 |
| US10314364B2 (en) | 2014-08-27 | 2019-06-11 | Nike, Inc. | Soil-shedding article of footwear, and method of using the same |
| US10064447B2 (en) | 2014-08-27 | 2018-09-04 | Nike, Inc. | Article of footwear with soil-shedding performance |
| US10675609B2 (en) | 2016-03-02 | 2020-06-09 | Nike, Inc. | Articles with soil-shedding performance |
| US10455893B2 (en) | 2016-03-02 | 2019-10-29 | Nike, Inc. | Hydrogel with mesh for soil deflection |
| US10362834B2 (en) | 2016-03-02 | 2019-07-30 | Nike, Inc. | Hydrogel connection |
| US10531705B2 (en) | 2016-03-02 | 2020-01-14 | Nike, Inc. | Hydrogel tie layer |
| CR20180455A (es) * | 2016-03-31 | 2019-01-14 | Lubrizol Advanced Mat Inc | Composiciones de poliuretano termoplástico para la fabricación de forma libre sólida de componentes y dispositivos médicos y para el cuidado bucal |
| CR20240188A (es) * | 2016-06-28 | 2024-07-01 | Lubrizol Advanced Mat Inc | Artículos fabricados a partir de composiciones de poliuretano termoplástico hidrófilo |
| CN107383325B (zh) * | 2017-06-28 | 2020-02-07 | 苏州奥斯汀新材料科技有限公司 | 一种高透明热塑性聚氨酯弹性体的制备方法 |
| TWI700175B (zh) | 2017-08-01 | 2020-08-01 | 荷蘭商耐基創新公司 | 製造用於鞋類物品之外底的組件之方法 |
| US11001031B2 (en) | 2017-10-19 | 2021-05-11 | Nike, Inc. | Composite materials, methods of making, methods of use, and articles incorporating the composite materials |
| BR112020009775A2 (pt) | 2017-12-14 | 2020-11-03 | Basf Se | método de preparação de poliuretano termoplástico, poliuretano termoplástico, uso, método de produção de partículas, partículas, espuma e uso das partículas |
| CN113527625B (zh) * | 2021-08-06 | 2022-02-22 | 盛鼎高新材料有限公司 | 聚氨酯弹性体预制物及聚氨酯弹性体的生产方法 |
| CN113754858A (zh) * | 2021-09-30 | 2021-12-07 | 宁波长阳科技股份有限公司 | 热塑性聚氨酯材料、热塑性聚氨酯膜及包含其的隐形车衣 |
| CN116217882A (zh) * | 2022-12-07 | 2023-06-06 | 山东一诺威聚氨酯股份有限公司 | 隐形车衣高强度低雾度tpu及其制备方法 |
| FR3165550A1 (fr) * | 2024-08-13 | 2026-02-20 | Arkema France | Crampons de chaussure |
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| DE1147034B (de) * | 1961-07-26 | 1963-04-11 | Bayer Ag | Verfahren zur Herstellung hochmolekularer vernetzter Kunststoffe auf Polyurethanbasis |
| DE2817456A1 (de) * | 1978-04-21 | 1979-10-31 | Bayer Ag | Verfahren zur herstellung von thermoplastischen polyurethanelastomeren |
| JPH09235343A (ja) * | 1995-12-28 | 1997-09-09 | Saint Gobain Vitrage | 架橋されたポリウレタン系樹脂シートおよびそれを用いた積層体 |
| EP0781792B1 (en) * | 1995-12-28 | 2002-02-06 | Asahi Glass Company Ltd. | Cross-linked polyurethane resin sheet and laminated product employing it |
| US6521164B1 (en) * | 1996-02-06 | 2003-02-18 | Parker-Hannifin Corporation | Injection-moldable thermoplastic polyurethane elastomer |
| DE69726581T2 (de) * | 1996-06-28 | 2004-09-16 | SK NJC Co. Ltd. | Verfahren zur herstellung von cyclohexandimethanol |
| US6252121B1 (en) * | 1999-07-27 | 2001-06-26 | Union Carbide Chemicals & Plastics Technology Corporation | Metal-ligand complex catalyzed processes |
| EP1353970A1 (en) * | 2000-12-19 | 2003-10-22 | Dow Global Technologies Inc. | Thermoplastic polyurethane containing structural units of ethylene oxide polyol or ethylene oxide capped propylene oxide polyol |
| US6806314B2 (en) | 2003-02-03 | 2004-10-19 | Ppg Industries Ohio, Inc. | Coating of Hydroxy-functional polymer(s), crosslinker, and 1,3- and 1,4-cyclohexane dimethanols |
| US8357768B2 (en) * | 2005-12-09 | 2013-01-22 | Hani Farah | Low haze thermoplastic polyurethane using co-chain extenders |
| ZA200806228B (en) * | 2006-02-03 | 2009-11-25 | Dow Global Technologies Inc | 1,3/1,4-cyclohexane dimethanol based monomers and polymers |
| CA2652297C (en) * | 2006-05-18 | 2014-09-02 | Dow Global Technologies Inc. | Polyurethane elastomer with enhanced hydrolysis resistance |
| AU2007253855A1 (en) * | 2006-05-18 | 2007-11-29 | Dow Global Technologies Llc | Polyurethane-urea polymers derived from cyclohexane dimethanol |
-
2007
- 2007-12-03 WO PCT/US2007/024753 patent/WO2008121133A1/en not_active Ceased
- 2007-12-03 BR BRPI0721405-7A patent/BRPI0721405B1/pt not_active IP Right Cessation
- 2007-12-03 CN CN2007800523337A patent/CN101652399B/zh not_active Expired - Fee Related
- 2007-12-03 US US12/593,377 patent/US8242228B2/en active Active
- 2007-12-03 ES ES07853220.7T patent/ES2467369T3/es active Active
- 2007-12-03 EP EP07853220.7A patent/EP2129700B1/en not_active Not-in-force
- 2007-12-03 KR KR1020097022665A patent/KR101447935B1/ko active Active
- 2007-12-03 JP JP2010500892A patent/JP5506659B2/ja active Active
-
2008
- 2008-03-17 TW TW097109305A patent/TWI443118B/zh active
Also Published As
| Publication number | Publication date |
|---|---|
| US20100113733A1 (en) | 2010-05-06 |
| JP5506659B2 (ja) | 2014-05-28 |
| KR20100016046A (ko) | 2010-02-12 |
| CN101652399B (zh) | 2013-02-20 |
| EP2129700B1 (en) | 2014-05-14 |
| CN101652399A (zh) | 2010-02-17 |
| BRPI0721405A2 (pt) | 2014-03-04 |
| WO2008121133A1 (en) | 2008-10-09 |
| BRPI0721405B1 (pt) | 2018-07-31 |
| TW200904845A (en) | 2009-02-01 |
| JP2010522799A (ja) | 2010-07-08 |
| KR101447935B1 (ko) | 2014-10-07 |
| EP2129700A1 (en) | 2009-12-09 |
| ES2467369T3 (es) | 2014-06-12 |
| US8242228B2 (en) | 2012-08-14 |
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