JP2014531489A5 - - Google Patents
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- JP2014531489A5 JP2014531489A5 JP2014530944A JP2014530944A JP2014531489A5 JP 2014531489 A5 JP2014531489 A5 JP 2014531489A5 JP 2014530944 A JP2014530944 A JP 2014530944A JP 2014530944 A JP2014530944 A JP 2014530944A JP 2014531489 A5 JP2014531489 A5 JP 2014531489A5
- Authority
- JP
- Japan
- Prior art keywords
- composition
- polymer
- blend
- group
- acrylate
- 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
- 239000000203 mixture Substances 0.000 claims 79
- 229920000642 polymer Polymers 0.000 claims 23
- 239000000178 monomer Substances 0.000 claims 15
- 239000011347 resin Substances 0.000 claims 15
- 229920005989 resin Polymers 0.000 claims 15
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims 11
- 238000000034 method Methods 0.000 claims 11
- 239000003999 initiator Substances 0.000 claims 8
- -1 hydroxypropyl Chemical group 0.000 claims 7
- 150000004678 hydrides Chemical class 0.000 claims 5
- 239000002904 solvent Substances 0.000 claims 5
- 229910052723 transition metal Inorganic materials 0.000 claims 5
- 230000006835 compression Effects 0.000 claims 4
- 238000007906 compression Methods 0.000 claims 4
- 239000003085 diluting agent Substances 0.000 claims 4
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical class CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims 3
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical class C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 claims 3
- 239000007795 chemical reaction product Substances 0.000 claims 3
- 150000001875 compounds Chemical class 0.000 claims 3
- 238000000151 deposition Methods 0.000 claims 3
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 claims 3
- HCLJOFJIQIJXHS-UHFFFAOYSA-N 2-[2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOCCOC(=O)C=C HCLJOFJIQIJXHS-UHFFFAOYSA-N 0.000 claims 2
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 claims 2
- 244000028419 Styrax benzoin Species 0.000 claims 2
- 235000000126 Styrax benzoin Nutrition 0.000 claims 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims 2
- 235000008411 Sumatra benzointree Nutrition 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 239000003963 antioxidant agent Substances 0.000 claims 2
- 229960002130 benzoin Drugs 0.000 claims 2
- 239000012965 benzophenone Substances 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 239000003431 cross linking reagent Substances 0.000 claims 2
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical group CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 claims 2
- 239000000806 elastomer Substances 0.000 claims 2
- 229920001971 elastomer Polymers 0.000 claims 2
- 239000000945 filler Substances 0.000 claims 2
- 125000000524 functional group Chemical group 0.000 claims 2
- 229920001002 functional polymer Polymers 0.000 claims 2
- 235000019382 gum benzoic Nutrition 0.000 claims 2
- 239000000049 pigment Substances 0.000 claims 2
- 239000004014 plasticizer Substances 0.000 claims 2
- 239000003381 stabilizer Substances 0.000 claims 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 claims 1
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 claims 1
- UDLFPYGNSVVZOY-UHFFFAOYSA-N 1,2-diethoxyxanthen-9-one Chemical class C1=CC=C2C(=O)C3=C(OCC)C(OCC)=CC=C3OC2=C1 UDLFPYGNSVVZOY-UHFFFAOYSA-N 0.000 claims 1
- MSAHTMIQULFMRG-UHFFFAOYSA-N 1,2-diphenyl-2-propan-2-yloxyethanone Chemical class C=1C=CC=CC=1C(OC(C)C)C(=O)C1=CC=CC=C1 MSAHTMIQULFMRG-UHFFFAOYSA-N 0.000 claims 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims 1
- YNSNJGRCQCDRDM-UHFFFAOYSA-N 1-chlorothioxanthen-9-one Chemical class S1C2=CC=CC=C2C(=O)C2=C1C=CC=C2Cl YNSNJGRCQCDRDM-UHFFFAOYSA-N 0.000 claims 1
- FDSUVTROAWLVJA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCC(CO)(CO)COCC(CO)(CO)CO FDSUVTROAWLVJA-UHFFFAOYSA-N 0.000 claims 1
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical class C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 claims 1
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical class CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 claims 1
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical class C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 claims 1
- HFCUBKYHMMPGBY-UHFFFAOYSA-N 2-methoxyethyl prop-2-enoate Chemical compound COCCOC(=O)C=C HFCUBKYHMMPGBY-UHFFFAOYSA-N 0.000 claims 1
- NCNNNERURUGJAB-UHFFFAOYSA-N 3-[2,2-bis(3-prop-2-enoyloxypropoxymethyl)butoxy]propyl prop-2-enoate Chemical compound C=CC(=O)OCCCOCC(CC)(COCCCOC(=O)C=C)COCCCOC(=O)C=C NCNNNERURUGJAB-UHFFFAOYSA-N 0.000 claims 1
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 claims 1
- JHWGFJBTMHEZME-UHFFFAOYSA-N 4-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OCCCCOC(=O)C=C JHWGFJBTMHEZME-UHFFFAOYSA-N 0.000 claims 1
- SAPGBCWOQLHKKZ-UHFFFAOYSA-N 6-(2-methylprop-2-enoyloxy)hexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCCOC(=O)C(C)=C SAPGBCWOQLHKKZ-UHFFFAOYSA-N 0.000 claims 1
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 claims 1
- DNVJGJUGFFYUPT-UHFFFAOYSA-N 9h-fluorene-9-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)C3=CC=CC=C3C2=C1 DNVJGJUGFFYUPT-UHFFFAOYSA-N 0.000 claims 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims 1
- IISBACLAFKSPIT-UHFFFAOYSA-N Bisphenol A Natural products C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims 1
- FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 claims 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 claims 1
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 claims 1
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 claims 1
- 150000008062 acetophenones Chemical class 0.000 claims 1
- 150000003926 acrylamides Chemical class 0.000 claims 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims 1
- 150000008366 benzophenones Chemical class 0.000 claims 1
- 229930006711 bornane-2,3-dione Natural products 0.000 claims 1
- 125000002362 bornane-2,3-dione group Chemical group 0.000 claims 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims 1
- 229920001577 copolymer Polymers 0.000 claims 1
- 125000004386 diacrylate group Chemical group 0.000 claims 1
- AOGHCSIZRYOJRS-UHFFFAOYSA-N diphenylmethanone;2-[2-hydroxyethyl(methyl)amino]ethanol Chemical class OCCN(C)CCO.C=1C=CC=CC=1C(=O)C1=CC=CC=C1 AOGHCSIZRYOJRS-UHFFFAOYSA-N 0.000 claims 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 1
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 claims 1
- 229920001519 homopolymer Polymers 0.000 claims 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 1
- 239000004615 ingredient Substances 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims 1
- 229920000058 polyacrylate Polymers 0.000 claims 1
- 229920000728 polyester Polymers 0.000 claims 1
- 229920000193 polymethacrylate Polymers 0.000 claims 1
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 claims 1
- 238000010526 radical polymerization reaction Methods 0.000 claims 1
- 150000007964 xanthones Chemical class 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161536433P | 2011-09-19 | 2011-09-19 | |
| US61/536,433 | 2011-09-19 | ||
| PCT/US2012/055870 WO2013043573A2 (en) | 2011-09-19 | 2012-09-18 | Highly functionalized resin blends |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015193086A Division JP6088018B2 (ja) | 2011-09-19 | 2015-09-30 | 高官能化樹脂ブレンド |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014531489A JP2014531489A (ja) | 2014-11-27 |
| JP2014531489A5 true JP2014531489A5 (enExample) | 2015-11-19 |
| JP6055833B2 JP6055833B2 (ja) | 2016-12-27 |
Family
ID=47915074
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014530944A Expired - Fee Related JP6055833B2 (ja) | 2011-09-19 | 2012-09-18 | 高官能化樹脂ブレンド |
| JP2015193086A Expired - Fee Related JP6088018B2 (ja) | 2011-09-19 | 2015-09-30 | 高官能化樹脂ブレンド |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015193086A Expired - Fee Related JP6088018B2 (ja) | 2011-09-19 | 2015-09-30 | 高官能化樹脂ブレンド |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US9090765B2 (enExample) |
| EP (1) | EP2768900B1 (enExample) |
| JP (2) | JP6055833B2 (enExample) |
| KR (1) | KR101657475B1 (enExample) |
| CN (1) | CN103998518B (enExample) |
| CA (1) | CA2849071C (enExample) |
| DK (1) | DK2768900T3 (enExample) |
| MX (1) | MX344299B (enExample) |
| WO (1) | WO2013043573A2 (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20150123909A (ko) * | 2013-03-29 | 2015-11-04 | 호야 가부시키가이샤 | 코팅 조성물 |
| EP3230327A4 (en) * | 2014-12-08 | 2018-07-18 | Henkel IP & Holding GmbH | Process for making branched reactive block polymers |
| US9587062B2 (en) * | 2014-12-15 | 2017-03-07 | Henkel IP & Holding GmbH and Henkel AG & Co. KGaA | Photocrosslinkable block copolymers for hot-melt adhesives |
| EP3034520A1 (de) * | 2014-12-19 | 2016-06-22 | HILTI Aktiengesellschaft | Reaktionsharz-Zusammensetzung und deren Verwendung |
| WO2016111743A1 (en) | 2015-01-08 | 2016-07-14 | Henkel IP & Holding GmbH | Process for preparing high molecular weight polyacrylates having narrow polydispersity indices |
| KR102351378B1 (ko) * | 2015-07-20 | 2022-01-20 | 삼성디스플레이 주식회사 | 점착제 조성물 및 표시장치 |
| CN107216419B (zh) * | 2017-05-23 | 2019-07-26 | 常州大学 | 一种制备高浓度羟基聚丙烯酸树脂及其固化的方法 |
| WO2019083876A1 (en) | 2017-10-26 | 2019-05-02 | Carbon, Inc. | REDUCTION OF WITHDRAWAL OR LOWERING IN OBJECTS PRODUCED BY ADDITIVE MANUFACTURING |
| US11535714B2 (en) | 2017-11-20 | 2022-12-27 | Carbon, Inc. | Light-curable siloxane resins for additive manufacturing |
| WO2019112707A1 (en) | 2017-12-08 | 2019-06-13 | Carbon, Inc. | Shelf stable, low tin concentration, dual cure additive manufacturing resins |
| WO2019168807A1 (en) | 2018-03-02 | 2019-09-06 | Carbon, Inc. | Sustainable additive manufacturing resins and methods of recycling |
| WO2021146237A1 (en) | 2020-01-17 | 2021-07-22 | Carbon, Inc. | Chemical recycling of additively manufactured objects |
| WO2025080931A1 (en) | 2023-10-12 | 2025-04-17 | Carbon, Inc. | Dual cure resins for mixed modulus materials |
| WO2025137013A1 (en) | 2023-12-19 | 2025-06-26 | Carbon, Inc. | Silicone resin compositions and methods of using same |
| WO2026064272A1 (en) | 2024-09-18 | 2026-03-26 | Carbon, Inc. | Production of low-density products using moisture curable resins |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5264030B2 (ja) | 1999-03-23 | 2013-08-14 | カーネギー−メロン ユニバーシティ | フリーラジカル的に（共）重合可能なモノマーの制御された重合のための触媒法、およびそれによって製造される官能性高分子系 |
| DE10036801A1 (de) * | 2000-07-28 | 2002-02-07 | Tesa Ag | Acrylathaftklebemassen mit enger Molekulargewichtsverteilung |
| DE10149084A1 (de) | 2001-10-05 | 2003-06-18 | Tesa Ag | UV-vernetzbare Acrylathaftschmelzhaftkleber mit enger Molekulargewichtsverteilung |
| EP1433799A3 (en) * | 2002-12-23 | 2004-07-14 | Ucb, S.A. | Star shaped acrylic block copolymer |
| CA2558968A1 (en) * | 2004-03-11 | 2005-09-22 | Kaneka Corporation | Active energy curing type composition for in-place shaping gasket and in-place shaped gasket |
| CN101087812B (zh) | 2004-10-25 | 2013-03-06 | 卢布里佐尔公司 | 制备聚合物及其组合物的方法 |
| TWI437054B (zh) * | 2006-12-08 | 2014-05-11 | Nippon Catalytic Chem Ind | Composition for coating material |
| JP2009292981A (ja) * | 2008-06-06 | 2009-12-17 | Kaneka Corp | 活性エネルギー線硬化性接着剤組成物とそれを用いた接着剤および光学ディスク装置 |
| CN102057001A (zh) * | 2008-06-06 | 2011-05-11 | 株式会社钟化 | 难粘合基材用粘合剂组合物以及使用其的粘合剂和光盘装置 |
| BRPI0914145A2 (pt) * | 2008-06-18 | 2015-10-20 | Henkel Corp | métodos para produzir polimerização por radical controlada, e para obter distribuição por radical atva controlada. |
| US20110213091A1 (en) * | 2008-11-12 | 2011-09-01 | Evonik Roehm Gmbh | Method for producing telechelics having a bimodal molecular weight distribution |
| DE102008043666A1 (de) * | 2008-11-12 | 2010-05-20 | Evonik Röhm Gmbh | Verfahren zur Herstellung von AB-Diblockcopolymeren mit einem bimodalen verteilten A-Block |
| JP5499501B2 (ja) * | 2009-03-17 | 2014-05-21 | 東亞合成株式会社 | 接着剤組成物 |
| JP2012145751A (ja) * | 2011-01-12 | 2012-08-02 | Nippon Shokubai Co Ltd | 光学用紫外線硬化型樹脂組成物、硬化物及び表示装置 |
-
2012
- 2012-09-18 JP JP2014530944A patent/JP6055833B2/ja not_active Expired - Fee Related
- 2012-09-18 DK DK12834357.1T patent/DK2768900T3/da active
- 2012-09-18 CA CA2849071A patent/CA2849071C/en not_active Expired - Fee Related
- 2012-09-18 WO PCT/US2012/055870 patent/WO2013043573A2/en not_active Ceased
- 2012-09-18 US US14/345,863 patent/US9090765B2/en active Active
- 2012-09-18 CN CN201280053589.0A patent/CN103998518B/zh not_active Expired - Fee Related
- 2012-09-18 EP EP12834357.1A patent/EP2768900B1/en active Active
- 2012-09-18 KR KR1020147010108A patent/KR101657475B1/ko not_active Expired - Fee Related
- 2012-09-18 MX MX2014003258A patent/MX344299B/es active IP Right Grant
-
2015
- 2015-09-30 JP JP2015193086A patent/JP6088018B2/ja not_active Expired - Fee Related
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