JPWO2020234697A5 - - Google Patents
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- Publication number
- JPWO2020234697A5 JPWO2020234697A5 JP2021568504A JP2021568504A JPWO2020234697A5 JP WO2020234697 A5 JPWO2020234697 A5 JP WO2020234697A5 JP 2021568504 A JP2021568504 A JP 2021568504A JP 2021568504 A JP2021568504 A JP 2021568504A JP WO2020234697 A5 JPWO2020234697 A5 JP WO2020234697A5
- Authority
- JP
- Japan
- Prior art keywords
- layer
- diisocyanate
- bead
- article
- polyurethane
- 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
- 239000010410 layer Substances 0.000 claims description 58
- 239000004814 polyurethane Substances 0.000 claims description 24
- 229920002635 polyurethane Polymers 0.000 claims description 24
- 150000002009 diols Chemical class 0.000 claims description 21
- 239000004005 microsphere Substances 0.000 claims description 13
- 229920005862 polyol Polymers 0.000 claims description 12
- 150000003077 polyols Chemical class 0.000 claims description 10
- 239000011541 reaction mixture Substances 0.000 claims description 10
- 229920002725 thermoplastic elastomer Polymers 0.000 claims description 10
- 239000011324 bead Substances 0.000 claims description 8
- 229920001187 thermosetting polymer Polymers 0.000 claims description 7
- 239000004970 Chain extender Substances 0.000 claims description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical group OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- -1 poly(hexamethylene diisocyanate) Polymers 0.000 claims description 6
- 239000002356 single layer Substances 0.000 claims description 6
- 229920000642 polymer Polymers 0.000 claims description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims description 4
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 4
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 4
- 238000009739 binding Methods 0.000 claims description 4
- 239000004202 carbamide Substances 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 229920001577 copolymer Polymers 0.000 claims description 4
- 125000005442 diisocyanate group Chemical group 0.000 claims description 4
- 229920001971 elastomer Polymers 0.000 claims description 4
- 239000000806 elastomer Substances 0.000 claims description 4
- 230000009477 glass transition Effects 0.000 claims description 4
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 4
- 230000000269 nucleophilic effect Effects 0.000 claims description 4
- 229920000162 poly(ureaurethane) Polymers 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
- 229920000570 polyether Polymers 0.000 claims description 4
- 239000005056 polyisocyanate Substances 0.000 claims description 4
- 229920001228 polyisocyanate Polymers 0.000 claims description 4
- 229920000098 polyolefin Polymers 0.000 claims description 4
- 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 4
- 239000004820 Pressure-sensitive adhesive Substances 0.000 claims description 3
- 239000000853 adhesive Substances 0.000 claims description 3
- 230000001070 adhesive effect Effects 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 claims description 2
- RTTZISZSHSCFRH-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC(CN=C=O)=C1 RTTZISZSHSCFRH-UHFFFAOYSA-N 0.000 claims description 2
- VGHSXKTVMPXHNG-UHFFFAOYSA-N 1,3-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC(N=C=O)=C1 VGHSXKTVMPXHNG-UHFFFAOYSA-N 0.000 claims description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 2
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 claims description 2
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 claims description 2
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 claims description 2
- QUPKOUOXSNGVLB-UHFFFAOYSA-N 1,8-diisocyanatooctane Chemical compound O=C=NCCCCCCCCN=C=O QUPKOUOXSNGVLB-UHFFFAOYSA-N 0.000 claims description 2
- AULVDVFFHZBVDO-UHFFFAOYSA-N 1-chloro-2,4-diisocyanato-5-methylbenzene Chemical compound CC1=CC(Cl)=C(N=C=O)C=C1N=C=O AULVDVFFHZBVDO-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 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
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 2
- UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 claims description 2
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 2
- 239000012790 adhesive layer Substances 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 239000011248 coating agent Substances 0.000 claims description 2
- 238000000576 coating method Methods 0.000 claims description 2
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical group C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 claims description 2
- JXCHMDATRWUOAP-UHFFFAOYSA-N diisocyanatomethylbenzene Chemical compound O=C=NC(N=C=O)C1=CC=CC=C1 JXCHMDATRWUOAP-UHFFFAOYSA-N 0.000 claims description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims description 2
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 2
- 229920000728 polyester Polymers 0.000 claims description 2
- 229920005906 polyester polyol Polymers 0.000 claims description 2
- 229920000193 polymethacrylate Polymers 0.000 claims description 2
- 229920001296 polysiloxane Polymers 0.000 claims description 2
- 229920000166 polytrimethylene carbonate Polymers 0.000 claims description 2
- 230000005855 radiation Effects 0.000 claims description 2
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 claims description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000003981 vehicle Substances 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 239000001273 butane Substances 0.000 claims 1
- 239000012948 isocyanate Substances 0.000 claims 1
- 150000002513 isocyanates Chemical class 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201962849665P | 2019-05-17 | 2019-05-17 | |
| US62/849,665 | 2019-05-17 | ||
| PCT/IB2020/054532 WO2020234697A1 (en) | 2019-05-17 | 2020-05-13 | Microsphere-coated polyurethane articles and methods of making the same |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| JP2022533156A JP2022533156A (ja) | 2022-07-21 |
| JPWO2020234697A5 true JPWO2020234697A5 (https=) | 2023-05-22 |
| JP2022533156A5 JP2022533156A5 (https=) | 2023-05-22 |
| JP7555358B2 JP7555358B2 (ja) | 2024-09-24 |
Family
ID=70918732
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021568504A Active JP7555358B2 (ja) | 2019-05-17 | 2020-05-13 | 微小球被覆ポリウレタン物品及びそれを作製する方法 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US12122127B2 (https=) |
| EP (1) | EP3969279B1 (https=) |
| JP (1) | JP7555358B2 (https=) |
| CN (1) | CN113825642B (https=) |
| WO (1) | WO2020234697A1 (https=) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP4136146A1 (en) * | 2020-04-17 | 2023-02-22 | 3M Innovative Properties Company | Microsphere-coated polyurethane articles and methods of making the same |
| WO2022085824A1 (ko) * | 2020-10-22 | 2022-04-28 | 엘지전자 주식회사 | 커버 글래스, 커버 글래스 제조방법 및 이동 단말기 |
Family Cites Families (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USRE24906E (en) | 1955-11-18 | 1960-12-13 | Pressure-sensitive adhesive sheet material | |
| US3331729A (en) | 1963-02-14 | 1967-07-18 | Minnesota Mining & Mfg | Adhesive bonding method and product |
| US3700305A (en) | 1970-12-14 | 1972-10-24 | Minnesota Mining & Mfg | Retroreflective microspheres having a dielectric mirror on a portion of their surface and retroreflective constructions containing such microspheres |
| US4418120A (en) | 1982-07-19 | 1983-11-29 | Minnesota Mining And Manufacturing Co. | Tackified crosslinked acrylic adhesives |
| CA1244306A (en) | 1982-09-02 | 1988-11-08 | Louis C. Belisle | Retroreflective sheeting |
| US4725494A (en) * | 1982-09-02 | 1988-02-16 | Minnesota Mining And Manufacturing Co. | Retroreflective sheeting |
| US4619867A (en) | 1983-06-14 | 1986-10-28 | Minnesota Mining And Manufacturing Company | Azlactone-containing pressure-sensitive adhesives |
| KR880700037A (ko) | 1985-07-08 | 1988-02-15 | 도날드 밀러 셀 | 교차 결합된 압감 접착제 |
| US4835217A (en) | 1985-10-17 | 1989-05-30 | Minnesota Mining And Manufacturing Company | Pressure-sensitive adhesive having broad useful temperature range |
| JP2546853B2 (ja) | 1987-09-03 | 1996-10-23 | オーツタイヤ株式会社 | 装飾性ビーズコートシートおよびその製造方法 |
| US5620775A (en) | 1995-11-03 | 1997-04-15 | Minnesota Mining And Manufacturing Company | Low refractive index glass microsphere coated article having a smooth surface and a method for preparing same |
| EP0863813B1 (en) * | 1995-11-22 | 2002-01-02 | Minnesota Mining And Manufacturing Company | Durable pavement marking tape with screencoated polyurethane topcoat |
| KR20030028832A (ko) * | 2000-09-01 | 2003-04-10 | 쓰리엠 이노베이티브 프로퍼티즈 캄파니 | 비닐막에 적층된 광 코어를 가진 시이트, 재귀반사 물품및 이의 제조 방법 |
| AU2002363242A1 (en) | 2001-10-31 | 2003-05-12 | 3M Innovative Properties Company | Cross-linked primer composition and use thereof in thermoformable films |
| EP2081769B1 (en) | 2006-10-04 | 2016-08-10 | 3M Innovative Properties Company | Method of making multilayer polyurethane protective film |
| US20090246439A1 (en) | 2008-03-31 | 2009-10-01 | 3M Innovative Properties Company | Decorative sheet |
| CN102893188B (zh) * | 2010-05-25 | 2016-11-02 | 3M创新有限公司 | 外露透镜逆反射制品 |
| EP2581216A1 (en) | 2011-10-12 | 2013-04-17 | Dow Global Technologies LLC | Panel with fire barrier |
| WO2013126361A1 (en) | 2012-02-22 | 2013-08-29 | 3M Innovative Properties Company | Microsphere articles and transfer articles |
| TWM436561U (en) * | 2012-04-27 | 2012-09-01 | Chaei Hsin Entpr Co Ltd | Reflection film structure for preformed structural component |
| JP6388589B2 (ja) | 2012-10-04 | 2018-09-12 | スリーエム イノベイティブ プロパティズ カンパニー | 熱成形可能な微小球物品 |
| CN103792604B (zh) | 2012-10-26 | 2016-12-21 | 3M创新有限公司 | 回归反射制品和附饰物 |
| US20150343502A1 (en) | 2012-12-20 | 2015-12-03 | 3M Innovative Properties Company | Anti-soiling, abrasion resistant constructions and methods of making |
| CN105683305B (zh) | 2013-06-26 | 2018-11-13 | 3M创新有限公司 | 耐污染性微球体制品 |
| KR102300849B1 (ko) | 2014-02-13 | 2021-09-13 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 이중 경화 내오염성 미소구체 물품 |
| WO2015153701A1 (en) | 2014-04-02 | 2015-10-08 | 3M Innovative Properties Company | Abrasion resistant microsphere articles |
| US10545268B2 (en) | 2014-05-09 | 2020-01-28 | 3M Innovative Properties Company | Retroreflective articles |
| CN105891924B (zh) | 2015-02-13 | 2019-07-09 | 3M创新有限公司 | 具有高温稳定性的柔性微球制品 |
| CN108139515B (zh) | 2015-07-07 | 2021-05-04 | 3M创新有限公司 | 用于光定向制品的聚氨酯层 |
| DE112016003676T5 (de) | 2015-08-12 | 2018-05-30 | 3M Innovative Properties Company | Chemikalienbeständige Mikrokügelchen-Artikel |
| JP6838857B2 (ja) | 2015-12-07 | 2021-03-03 | スリーエム イノベイティブ プロパティズ カンパニー | 積層体、接着キット、積層構造体及びその製造方法、並びにコンタクト接着剤組成物 |
| EP3390070B1 (en) | 2015-12-18 | 2022-04-06 | 3M Innovative Properties Company | Decorative article featuring a microscopic periodic pattern and methods of making the same |
| JP2019512015A (ja) | 2016-02-26 | 2019-05-09 | ザ・ジョンズ・ホプキンス・ユニバーシティ | 機械的刺激による痛みに関連する電位依存性ナトリウム・チャネルＮａｖ１．１に対する調節薬 |
| US11413846B2 (en) | 2016-03-30 | 2022-08-16 | 3M Innovative Properties Company | Article featuring a predetermined pattern of randomly distributed microspheres and methods of making the same |
| US11112544B2 (en) * | 2016-08-12 | 2021-09-07 | 3M Innovative Properties Company | Truncated beadfilm constructions and methods of making the same |
| EP3676092A1 (en) | 2017-08-31 | 2020-07-08 | 3M Innovative Properties Company | Shaped transfer article comprising partially embedded microspheres, shaped finished articles therefrom, and methods of making |
| EP3684832A1 (en) | 2017-09-21 | 2020-07-29 | 3M Innovative Properties Company | Extruded polyurethane surface films |
-
2020
- 2020-05-13 US US17/605,035 patent/US12122127B2/en active Active
- 2020-05-13 JP JP2021568504A patent/JP7555358B2/ja active Active
- 2020-05-13 EP EP20729184.0A patent/EP3969279B1/en active Active
- 2020-05-13 CN CN202080035546.4A patent/CN113825642B/zh active Active
- 2020-05-13 WO PCT/IB2020/054532 patent/WO2020234697A1/en not_active Ceased
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