JP6300805B2 - 放射線硬化性インク組成物 - Google Patents
放射線硬化性インク組成物 Download PDFInfo
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- JP6300805B2 JP6300805B2 JP2015534464A JP2015534464A JP6300805B2 JP 6300805 B2 JP6300805 B2 JP 6300805B2 JP 2015534464 A JP2015534464 A JP 2015534464A JP 2015534464 A JP2015534464 A JP 2015534464A JP 6300805 B2 JP6300805 B2 JP 6300805B2
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- acrylate
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- ink
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- 230000005855 radiation Effects 0.000 title claims description 90
- 239000000203 mixture Substances 0.000 title claims description 86
- -1 2,2,6,6-tetramethylpiperidinyl compound Chemical class 0.000 claims description 120
- 239000000376 reactant Substances 0.000 claims description 89
- 230000001588 bifunctional effect Effects 0.000 claims description 62
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 239000003086 colorant Substances 0.000 claims description 11
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 10
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- 125000003277 amino group Chemical group 0.000 claims description 4
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- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 64
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- 238000012360 testing method Methods 0.000 description 27
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- ZJZCLKUUALUYKT-UHFFFAOYSA-N (2,2,6,6-tetramethylpiperidin-1-ium-1-ylidene)azanide Chemical group CC1(C)CCCC(C)(C)[N+]1=[N-] ZJZCLKUUALUYKT-UHFFFAOYSA-N 0.000 description 7
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- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
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- JZMPIUODFXBXSC-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.CCOC(N)=O JZMPIUODFXBXSC-UHFFFAOYSA-N 0.000 description 4
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- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
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- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 3
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- LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical compound CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 description 3
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 3
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- GNWBLLYJQXKPIP-ZOGIJGBBSA-N (1s,3as,3bs,5ar,9ar,9bs,11as)-n,n-diethyl-6,9a,11a-trimethyl-7-oxo-2,3,3a,3b,4,5,5a,8,9,9b,10,11-dodecahydro-1h-indeno[5,4-f]quinoline-1-carboxamide Chemical compound CN([C@@H]1CC2)C(=O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](C(=O)N(CC)CC)[C@@]2(C)CC1 GNWBLLYJQXKPIP-ZOGIJGBBSA-N 0.000 description 2
- PJAKWOZHTFWTNF-UHFFFAOYSA-N (2-nonylphenyl) prop-2-enoate Chemical compound CCCCCCCCCC1=CC=CC=C1OC(=O)C=C PJAKWOZHTFWTNF-UHFFFAOYSA-N 0.000 description 2
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 2
- JWYVGKFDLWWQJX-UHFFFAOYSA-N 1-ethenylazepan-2-one Chemical compound C=CN1CCCCCC1=O JWYVGKFDLWWQJX-UHFFFAOYSA-N 0.000 description 2
- JLZIIHMTTRXXIN-UHFFFAOYSA-N 2-(2-hydroxy-4-methoxybenzoyl)benzoic acid Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1C(O)=O JLZIIHMTTRXXIN-UHFFFAOYSA-N 0.000 description 2
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- STEYNUVPFMIUOY-UHFFFAOYSA-N 4-Hydroxy-1-(2-hydroxyethyl)-2,2,6,6-tetramethylpiperidine Chemical compound CC1(C)CC(O)CC(C)(C)N1CCO STEYNUVPFMIUOY-UHFFFAOYSA-N 0.000 description 2
- DXPPIEDUBFUSEZ-UHFFFAOYSA-N 6-methylheptyl prop-2-enoate Chemical compound CC(C)CCCCCOC(=O)C=C DXPPIEDUBFUSEZ-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
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- RSOILICUEWXSLA-UHFFFAOYSA-N bis(1,2,2,6,6-pentamethylpiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)N(C)C(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)N(C)C(C)(C)C1 RSOILICUEWXSLA-UHFFFAOYSA-N 0.000 description 2
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- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
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- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/10—Printing inks based on artificial resins
- C09D11/101—Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/10—Printing inks based on artificial resins
- C09D11/106—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C09D11/107—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds from unsaturated acids or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/32—Inkjet printing inks characterised by colouring agents
- C09D11/322—Pigment inks
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- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
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| US201361772408P | 2013-03-04 | 2013-03-04 | |
| US61/772,408 | 2013-03-04 | ||
| PCT/US2013/033039 WO2014051702A1 (en) | 2012-09-25 | 2013-03-20 | Radiation curable ink composition |
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| US9961745B2 (en) | 2013-11-21 | 2018-05-01 | Ford Global Technologies, Llc | Printed LED rylene dye welcome/farewell lighting |
| US9873180B2 (en) | 2014-10-17 | 2018-01-23 | Applied Materials, Inc. | CMP pad construction with composite material properties using additive manufacturing processes |
| CN107078048B (zh) | 2014-10-17 | 2021-08-13 | 应用材料公司 | 使用加成制造工艺的具复合材料特性的cmp衬垫建构 |
| US11745302B2 (en) | 2014-10-17 | 2023-09-05 | Applied Materials, Inc. | Methods and precursor formulations for forming advanced polishing pads by use of an additive manufacturing process |
| US9776361B2 (en) | 2014-10-17 | 2017-10-03 | Applied Materials, Inc. | Polishing articles and integrated system and methods for manufacturing chemical mechanical polishing articles |
| US10875153B2 (en) | 2014-10-17 | 2020-12-29 | Applied Materials, Inc. | Advanced polishing pad materials and formulations |
| GB201509501D0 (en) * | 2015-06-02 | 2015-07-15 | Fujifilm Speciality Ink Systems Ltd | A printing ink |
| US10492888B2 (en) * | 2015-07-07 | 2019-12-03 | Align Technology, Inc. | Dental materials using thermoset polymers |
| US10457825B2 (en) | 2015-08-17 | 2019-10-29 | Electronics For Imaging, Inc. | UV curable inkjet ink compositions |
| EP4279553A3 (en) * | 2015-09-14 | 2024-02-28 | Maxell, Ltd. | Ink composition, process for producing same, and ink-jet ink set and ink-jet printing system both including said ink composition |
| KR20230169424A (ko) | 2015-10-30 | 2023-12-15 | 어플라이드 머티어리얼스, 인코포레이티드 | 원하는 제타 전위를 가진 연마 제품을 형성하는 장치 및 방법 |
| US10593574B2 (en) | 2015-11-06 | 2020-03-17 | Applied Materials, Inc. | Techniques for combining CMP process tracking data with 3D printed CMP consumables |
| US10391605B2 (en) | 2016-01-19 | 2019-08-27 | Applied Materials, Inc. | Method and apparatus for forming porous advanced polishing pads using an additive manufacturing process |
| US10108087B2 (en) | 2016-03-11 | 2018-10-23 | Macdermid Graphics Solutions Llc | Method of improving light stability of flexographic printing plates featuring flat top dots |
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| CN110573583B (zh) * | 2017-05-24 | 2022-08-02 | Dic株式会社 | 活性能量射线固化性油墨和印刷物的制造方法 |
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| US11471999B2 (en) | 2017-07-26 | 2022-10-18 | Applied Materials, Inc. | Integrated abrasive polishing pads and manufacturing methods |
| CN109321145B (zh) * | 2017-07-31 | 2022-01-04 | 东洋油墨Sc控股株式会社 | 光学用活性能量线聚合性粘接剂及光学用层叠体 |
| WO2019032286A1 (en) | 2017-08-07 | 2019-02-14 | Applied Materials, Inc. | ABRASIVE DISTRIBUTION POLISHING PADS AND METHODS OF MAKING SAME |
| JP6932243B2 (ja) | 2018-03-27 | 2021-09-08 | 富士フイルム株式会社 | 光硬化性インク組成物及び画像形成方法 |
| EP3778792B1 (en) * | 2018-03-27 | 2025-01-22 | FUJIFILM Corporation | Photocurable ink composition and image forming method |
| CN112654655A (zh) | 2018-09-04 | 2021-04-13 | 应用材料公司 | 先进抛光垫配方 |
| JP7320185B2 (ja) * | 2019-02-08 | 2023-08-03 | セイコーエプソン株式会社 | 放射線硬化型インクジェット組成物及び記録方法 |
| JP7338167B2 (ja) * | 2019-02-28 | 2023-09-05 | セイコーエプソン株式会社 | インク組成物 |
| US11851570B2 (en) | 2019-04-12 | 2023-12-26 | Applied Materials, Inc. | Anionic polishing pads formed by printing processes |
| JP7656398B2 (ja) | 2019-06-17 | 2025-04-03 | セイコーエプソン株式会社 | 放射線硬化型インクジェット組成物及びインクジェット方法 |
| DE102019130152A1 (de) * | 2019-11-08 | 2021-05-12 | Heidelberger Druckmaschinen Ag | Verfahren zum Drucken auf eine Schicht mit stabilem radikalischem Photoinitiator |
| JP7648338B2 (ja) | 2019-11-20 | 2025-03-18 | スリーエム イノベイティブ プロパティズ カンパニー | 無機ナノ粒子含有耐摩耗層を含む積層体、及び低粘度の無機ナノ粒子含有放射線硬化型インク |
| JP2021113273A (ja) * | 2020-01-17 | 2021-08-05 | 株式会社リコー | 活性エネルギー線硬化型組成物、活性エネルギー線硬化型インク組成物、活性エネルギー線硬化型インクジェット用インク組成物、２次元または３次元の像形成装置、２次元または３次元の像形成方法、硬化物及び加飾体 |
| JP7435121B2 (ja) | 2020-03-25 | 2024-02-21 | セイコーエプソン株式会社 | 放射線硬化型インクジェット組成物及びインクジェット方法 |
| JP7463795B2 (ja) | 2020-03-25 | 2024-04-09 | セイコーエプソン株式会社 | 放射線硬化型インクジェット組成物及びインクジェット方法 |
| JP2022107267A (ja) * | 2021-01-08 | 2022-07-21 | セイコーエプソン株式会社 | 放射線硬化型インクジェット組成物及びインクセット |
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| WO2002038688A2 (en) | 2000-11-09 | 2002-05-16 | 3M Innovative Properties Company | Weather resistant, ink jettable, radiation curable, fluid compositions particularly suitable for outdoor applications |
| US6869648B2 (en) * | 2002-06-18 | 2005-03-22 | Hewlett-Packard Development Company, L.P. | Use of monomeric and oligomeric additives to stabilize dyes on porous ink jet media |
| US7037952B2 (en) | 2002-08-02 | 2006-05-02 | Seiren Co., Ltd. | Ultraviolet ray curable ink, ink composition for ink jet and process for preparing ink jet printed matter using the same |
| JP4754779B2 (ja) | 2002-09-20 | 2011-08-24 | セーレン株式会社 | 紫外線硬化型インク |
| US20060211788A1 (en) * | 2005-03-18 | 2006-09-21 | Krohn Roy C | UV curable compositions for ink or paint applications |
| GB0608466D0 (en) * | 2006-04-27 | 2006-06-07 | Sericol Ltd | A printing ink |
| JP5189258B2 (ja) | 2006-07-28 | 2013-04-24 | 富士フイルム株式会社 | インク組成物、インクジェット記録方法、印刷物、及び、平版印刷版の製造方法 |
| JP2008105393A (ja) | 2006-09-25 | 2008-05-08 | Fujifilm Corp | 成形印刷物の製造方法及び成形印刷物 |
| JP4335950B2 (ja) * | 2008-02-05 | 2009-09-30 | 日立マクセル株式会社 | エネルギー線硬化型インク組成物 |
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| JP5461809B2 (ja) * | 2008-09-29 | 2014-04-02 | 富士フイルム株式会社 | インク組成物、及び、インクジェット記録方法 |
| JP5583595B2 (ja) * | 2008-11-21 | 2014-09-03 | 日立マクセル株式会社 | エネルギー線硬化型インクジェットインク組成物 |
| JP5349095B2 (ja) | 2009-03-17 | 2013-11-20 | 富士フイルム株式会社 | インク組成物、及び、インクジェット記録方法 |
| JP5803258B2 (ja) * | 2010-09-30 | 2015-11-04 | セイコーエプソン株式会社 | 紫外線硬化型インクジェット用インク組成物、インクジェット記録方法 |
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| US9718975B2 (en) | 2017-08-01 |
| EP2900774A4 (en) | 2016-07-06 |
| US20150252202A1 (en) | 2015-09-10 |
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