JP2013521374A5 - - Google Patents
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- Publication number
- JP2013521374A5 JP2013521374A5 JP2012556111A JP2012556111A JP2013521374A5 JP 2013521374 A5 JP2013521374 A5 JP 2013521374A5 JP 2012556111 A JP2012556111 A JP 2012556111A JP 2012556111 A JP2012556111 A JP 2012556111A JP 2013521374 A5 JP2013521374 A5 JP 2013521374A5
- Authority
- JP
- Japan
- Prior art keywords
- diisocyanate
- terminal
- elastomer
- lactamized
- polyurea
- Prior art date
- 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.)
- Granted
Links
- 229920001971 elastomer Polymers 0.000 claims description 43
- 239000000806 elastomer Substances 0.000 claims description 43
- 125000005442 diisocyanate group Chemical group 0.000 claims description 37
- 229920002396 Polyurea Polymers 0.000 claims description 30
- -1 alkylene diols Chemical class 0.000 claims description 27
- 229920005862 polyol Polymers 0.000 claims description 20
- DVPHDWQFZRBFND-DMHDVGBCSA-N 1-o-[2-[(3ar,5r,6s,6ar)-2,2-dimethyl-6-prop-2-enoyloxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-[4-[(2s,3r)-1-butan-2-ylsulfanyl-2-(2-chlorophenyl)-4-oxoazetidin-3-yl]oxy-4-oxobutanoyl]oxyethyl] 4-o-[(2s,3r)-1-butan-2-ylsulfanyl-2-(2-chloropheny Chemical group C1([C@H]2[C@H](C(N2SC(C)CC)=O)OC(=O)CCC(=O)OC(COC(=O)CCC(=O)O[C@@H]2[C@@H](N(C2=O)SC(C)CC)C=2C(=CC=CC=2)Cl)[C@@H]2[C@@H]([C@H]3OC(C)(C)O[C@H]3O2)OC(=O)C=C)=CC=CC=C1Cl DVPHDWQFZRBFND-DMHDVGBCSA-N 0.000 claims description 16
- 239000003054 catalyst Substances 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 16
- 150000003077 polyols Chemical class 0.000 claims description 16
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- 235000010290 biphenyl Nutrition 0.000 claims description 8
- 239000004305 biphenyl Substances 0.000 claims description 8
- 125000006267 biphenyl group Chemical group 0.000 claims description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 8
- 239000000654 additive Substances 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 239000000155 melt Substances 0.000 claims description 6
- 229920000642 polymer Polymers 0.000 claims description 6
- 238000006116 polymerization reaction Methods 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 229920001610 polycaprolactone Polymers 0.000 claims description 4
- 239000004632 polycaprolactone Substances 0.000 claims description 4
- 229920000515 polycarbonate Polymers 0.000 claims description 4
- 239000004417 polycarbonate Substances 0.000 claims description 4
- 229920000728 polyester Polymers 0.000 claims description 4
- 230000000379 polymerizing effect Effects 0.000 claims description 4
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 claims description 3
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 3
- 239000004609 Impact Modifier Substances 0.000 claims description 3
- 239000006057 Non-nutritive feed additive Substances 0.000 claims description 3
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 3
- 239000012963 UV stabilizer Substances 0.000 claims description 3
- 239000003963 antioxidant agent Substances 0.000 claims description 3
- 239000003086 colorant Substances 0.000 claims description 3
- 229920001940 conductive polymer Polymers 0.000 claims description 3
- 239000000945 filler Substances 0.000 claims description 3
- 239000003063 flame retardant Substances 0.000 claims description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 3
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims description 3
- 239000004611 light stabiliser Substances 0.000 claims description 3
- 239000000314 lubricant Substances 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 239000012764 mineral filler Substances 0.000 claims description 3
- 239000002105 nanoparticle Substances 0.000 claims description 3
- 239000002071 nanotube Substances 0.000 claims description 3
- 239000000049 pigment Substances 0.000 claims description 3
- 229920000570 polyether Polymers 0.000 claims description 3
- 239000003381 stabilizer Substances 0.000 claims description 3
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims 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 claims description 2
- 239000004952 Polyamide Substances 0.000 claims description 2
- KXBFLNPZHXDQLV-UHFFFAOYSA-N [cyclohexyl(diisocyanato)methyl]cyclohexane Chemical compound C1CCCCC1C(N=C=O)(N=C=O)C1CCCCC1 KXBFLNPZHXDQLV-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229920002647 polyamide Polymers 0.000 claims description 2
- 150000003951 lactams Chemical group 0.000 claims 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- GHLKSLMMWAKNBM-UHFFFAOYSA-N dodecane-1,12-diol Chemical compound OCCCCCCCCCCCCO GHLKSLMMWAKNBM-UHFFFAOYSA-N 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- RTTZISZSHSCFRH-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC(CN=C=O)=C1 RTTZISZSHSCFRH-UHFFFAOYSA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- 239000005059 1,4-Cyclohexyldiisocyanate Substances 0.000 description 1
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 1
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 1
- ICLCCFKUSALICQ-UHFFFAOYSA-N 1-isocyanato-4-(4-isocyanato-3-methylphenyl)-2-methylbenzene Chemical compound C1=C(N=C=O)C(C)=CC(C=2C=C(C)C(N=C=O)=CC=2)=C1 ICLCCFKUSALICQ-UHFFFAOYSA-N 0.000 description 1
- WTPYFJNYAMXZJG-UHFFFAOYSA-N 2-[4-(2-hydroxyethoxy)phenoxy]ethanol Chemical compound OCCOC1=CC=C(OCCO)C=C1 WTPYFJNYAMXZJG-UHFFFAOYSA-N 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- JHWNWJKBPDFINM-UHFFFAOYSA-N Laurolactam Chemical compound O=C1CCCCCCCCCCCN1 JHWNWJKBPDFINM-UHFFFAOYSA-N 0.000 description 1
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- INSRQEMEVAMETL-UHFFFAOYSA-N decane-1,1-diol Chemical compound CCCCCCCCCC(O)O INSRQEMEVAMETL-UHFFFAOYSA-N 0.000 description 1
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 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 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US30907910P | 2010-03-01 | 2010-03-01 | |
| US61/309,079 | 2010-03-01 | ||
| PCT/US2011/026023 WO2011109213A1 (en) | 2010-03-01 | 2011-02-24 | Melt processable copolyurea elastomers |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016131580A Division JP2016194084A (ja) | 2010-03-01 | 2016-07-01 | 溶融加工処理可能なポリウレアエラストマー |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013521374A JP2013521374A (ja) | 2013-06-10 |
| JP2013521374A5 true JP2013521374A5 (enExample) | 2014-03-20 |
| JP6014498B2 JP6014498B2 (ja) | 2016-10-25 |
Family
ID=43877233
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012556111A Active JP6014498B2 (ja) | 2010-03-01 | 2011-02-24 | 溶融加工処理可能なポリウレアエラストマー |
| JP2016131580A Withdrawn JP2016194084A (ja) | 2010-03-01 | 2016-07-01 | 溶融加工処理可能なポリウレアエラストマー |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016131580A Withdrawn JP2016194084A (ja) | 2010-03-01 | 2016-07-01 | 溶融加工処理可能なポリウレアエラストマー |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US20120316290A1 (enExample) |
| EP (1) | EP2542606B1 (enExample) |
| JP (2) | JP6014498B2 (enExample) |
| KR (1) | KR101799927B1 (enExample) |
| CN (1) | CN102781995B (enExample) |
| CA (1) | CA2790570C (enExample) |
| TW (1) | TWI546334B (enExample) |
| WO (1) | WO2011109213A1 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6014498B2 (ja) * | 2010-03-01 | 2016-10-25 | ルブリゾル アドバンスド マテリアルズ, インコーポレイテッド | 溶融加工処理可能なポリウレアエラストマー |
| BR112018069056B1 (pt) * | 2016-03-22 | 2022-07-26 | Lubrizol Advanced Materials, Inc | Elastômero de poliuretano-ureia termoplástico, e, processos para fabricação de composição de elastômero de poliuretano-ureia termoplástica processável por fusão e de um artigo moldado a partir de uma composição de poliuretano-ureia termoplástica |
| CN110452758A (zh) * | 2018-05-07 | 2019-11-15 | 天津科技大学 | 一种含有酰胺基与脲基的润滑脂的制备方法及所制得的产品 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3245961A (en) * | 1962-08-28 | 1966-04-12 | Nopco Chem Co | Polyureas from caprolactamblocked isocyanates |
| DE2215080C3 (de) * | 1972-03-28 | 1978-10-12 | Bayer Ag, 5090 Leverkusen | Pulverförmige Überzugsmittel |
| DE3220802C1 (de) * | 1982-06-03 | 1983-08-11 | Deutsche Gesellschaft für Wiederaufarbeitung von Kernbrennstoffen mbH, 3000 Hannover | Buendelschere in dezentralisierter Kompaktbauweise |
| US4578447A (en) * | 1983-12-28 | 1986-03-25 | Ex-Cell-O Corporation | Rim nylon-based urethane block polymer composition |
| US4673722A (en) * | 1985-12-23 | 1987-06-16 | General Motors Corporation | High impact nylon/polyurea copolymer |
| DE3711374A1 (de) * | 1987-04-04 | 1988-10-20 | Huels Chemische Werke Ag | Polyurethan-pulverlacke, die nach aushaertung eine matte oberflaeche ergeben |
| DE4118052A1 (de) * | 1991-06-01 | 1992-12-03 | Bayer Ag | Pulverlack und seine verwendung |
| DE4203297A1 (de) * | 1992-01-31 | 1993-08-05 | Fischer Karl Ind Gmbh | Verfahren zur herstellung von polyurethan- und/oder polyurethanharnstoff-elastomer |
| US5583196A (en) * | 1992-01-31 | 1996-12-10 | Karl Fischer Industrieanlagen Gmbh | Melt formed from polyurethane and/or polyurethane urea elastomer and method for producing the same |
| DE19602683C1 (de) * | 1996-01-25 | 1997-09-18 | Inventa Ag | Flüssigsystem zur Durchführung der anionischen Lactampolymerisation |
| DE19604581A1 (de) * | 1996-02-08 | 1997-08-14 | Bayer Ag | Polyurethan-Pulvermattlacke |
| JP6014498B2 (ja) * | 2010-03-01 | 2016-10-25 | ルブリゾル アドバンスド マテリアルズ, インコーポレイテッド | 溶融加工処理可能なポリウレアエラストマー |
| JP6489635B2 (ja) * | 2015-01-15 | 2019-03-27 | オリンパス株式会社 | 観察装置 |
-
2011
- 2011-02-24 JP JP2012556111A patent/JP6014498B2/ja active Active
- 2011-02-24 CN CN201180011691.XA patent/CN102781995B/zh active Active
- 2011-02-24 EP EP11707288.4A patent/EP2542606B1/en active Active
- 2011-02-24 KR KR1020127025544A patent/KR101799927B1/ko active Active
- 2011-02-24 WO PCT/US2011/026023 patent/WO2011109213A1/en not_active Ceased
- 2011-02-24 US US13/579,949 patent/US20120316290A1/en not_active Abandoned
- 2011-02-24 CA CA2790570A patent/CA2790570C/en active Active
- 2011-02-25 TW TW100106363A patent/TWI546334B/zh active
-
2016
- 2016-07-01 JP JP2016131580A patent/JP2016194084A/ja not_active Withdrawn
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