AU2013307478B2 - Low migration free radical radiation curable inkjet inks - Google Patents
Low migration free radical radiation curable inkjet inksInfo
- Publication number
- AU2013307478B2 AU2013307478B2 AU2013307478A AU2013307478A AU2013307478B2 AU 2013307478 B2 AU2013307478 B2 AU 2013307478B2 AU 2013307478 A AU2013307478 A AU 2013307478A AU 2013307478 A AU2013307478 A AU 2013307478A AU 2013307478 B2 AU2013307478 B2 AU 2013307478B2
- Authority
- AU
- Australia
- Prior art keywords
- radiation curable
- free radical
- curable inkjet
- inkjet ink
- group
- 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.)
- Ceased
Links
- 230000005855 radiation Effects 0.000 title claims abstract description 130
- 150000003254 radicals Chemical class 0.000 title claims abstract description 94
- 239000000976 ink Substances 0.000 title description 158
- 230000005012 migration Effects 0.000 title description 5
- 238000013508 migration Methods 0.000 title description 5
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 10
- 239000000178 monomer Substances 0.000 claims description 87
- -1 thiol compound Chemical class 0.000 claims description 71
- 239000000203 mixture Substances 0.000 claims description 39
- 239000000758 substrate Substances 0.000 claims description 36
- 150000001875 compounds Chemical class 0.000 claims description 28
- 238000004017 vitrification Methods 0.000 claims description 27
- 238000007641 inkjet printing Methods 0.000 claims description 24
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 23
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- 125000000524 functional group Chemical group 0.000 claims description 14
- 229920000642 polymer Polymers 0.000 claims description 11
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical group C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 claims description 10
- 239000004698 Polyethylene Substances 0.000 claims description 9
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- 125000000217 alkyl group Chemical group 0.000 claims description 7
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- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 claims description 5
- 239000003086 colorant Substances 0.000 claims description 4
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
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- 238000004458 analytical method Methods 0.000 description 3
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- GTPROMYYPGDANE-UHFFFAOYSA-N ethenoxyethene;prop-2-enoic acid Chemical class C=COC=C.OC(=O)C=C GTPROMYYPGDANE-UHFFFAOYSA-N 0.000 description 3
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- PSYGHMBJXWRQFD-UHFFFAOYSA-N 2-(2-sulfanylacetyl)oxyethyl 2-sulfanylacetate Chemical compound SCC(=O)OCCOC(=O)CS PSYGHMBJXWRQFD-UHFFFAOYSA-N 0.000 description 2
- JMWGZSWSTCGVLX-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;2-methylprop-2-enoic acid Chemical compound CC(=C)C(O)=O.CC(=C)C(O)=O.CC(=C)C(O)=O.CCC(CO)(CO)CO JMWGZSWSTCGVLX-UHFFFAOYSA-N 0.000 description 2
- RBDYMRWHRDPLOS-UHFFFAOYSA-N 4-(dimethylamino)-3-ethyl-2-hexylbenzoic acid Chemical compound CCCCCCC1=C(CC)C(N(C)C)=CC=C1C(O)=O RBDYMRWHRDPLOS-UHFFFAOYSA-N 0.000 description 2
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- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
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- 125000004985 dialkyl amino alkyl group Chemical group 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- 239000012972 dimethylethanolamine Substances 0.000 description 1
- 235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 1
- PODOEQVNFJSWIK-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethoxyphenyl)methanone Chemical compound COC1=CC(OC)=CC(OC)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 PODOEQVNFJSWIK-UHFFFAOYSA-N 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- YHAIUSTWZPMYGG-UHFFFAOYSA-L disodium;2,2-dioctyl-3-sulfobutanedioate Chemical compound [Na+].[Na+].CCCCCCCCC(C([O-])=O)(C(C([O-])=O)S(O)(=O)=O)CCCCCCCC YHAIUSTWZPMYGG-UHFFFAOYSA-L 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
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- 230000000694 effects Effects 0.000 description 1
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- 125000001033 ether group Chemical group 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
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- 235000004611 garlic Nutrition 0.000 description 1
- OXHDYFKENBXUEM-UHFFFAOYSA-N glyphosine Chemical compound OC(=O)CN(CP(O)(O)=O)CP(O)(O)=O OXHDYFKENBXUEM-UHFFFAOYSA-N 0.000 description 1
- 239000001056 green pigment Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
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- 230000006872 improvement Effects 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
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- 150000002500 ions Chemical class 0.000 description 1
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- 238000000691 measurement method Methods 0.000 description 1
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- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- FAQJJMHZNSSFSM-UHFFFAOYSA-N phenylglyoxylic acid Chemical class OC(=O)C(=O)C1=CC=CC=C1 FAQJJMHZNSSFSM-UHFFFAOYSA-N 0.000 description 1
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- MUTNCGKQJGXKEM-UHFFFAOYSA-N tamibarotene Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1NC(=O)C1=CC=C(C(O)=O)C=C1 MUTNCGKQJGXKEM-UHFFFAOYSA-N 0.000 description 1
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- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
Classifications
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- 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
-
- 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
- C09D11/30—Inkjet printing inks
- C09D11/38—Inkjet printing inks characterised by non-macromolecular additives other than solvents, pigments or dyes
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/24—Structurally defined web or sheet [e.g., overall dimension, etc.]
- Y10T428/24802—Discontinuous or differential coating, impregnation or bond [e.g., artwork, printing, retouched photograph, etc.]
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Ink Jet Recording Methods And Recording Media Thereof (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
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| EP12182522.8A EP2703457B1 (en) | 2012-08-31 | 2012-08-31 | Low migration free radical radiation curable inkjet inks |
| EP12182522.8 | 2012-08-31 | ||
| US201261696304P | 2012-09-04 | 2012-09-04 | |
| US61/696,304 | 2012-09-04 | ||
| PCT/EP2013/066936 WO2014032968A1 (en) | 2012-08-31 | 2013-08-13 | Low migration free radical radiation curable inkjet inks |
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| AU2013307478A1 AU2013307478A1 (en) | 2015-01-22 |
| AU2013307478B2 true AU2013307478B2 (en) | 2016-07-14 |
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| AT519733B1 (de) * | 2012-06-06 | 2019-08-15 | Agfa Nv | Strahlungshärtbare Tintenstrahltinten und industrielle Tintenstrahldruckverfahren |
| JP5632978B1 (ja) * | 2013-06-28 | 2014-11-26 | 太陽インキ製造株式会社 | 光硬化性組成物およびその硬化物 |
| US20160230014A1 (en) * | 2013-09-13 | 2016-08-11 | Basf Se | Scratch-resistant radiation-cured coatings |
| ES2651138T3 (es) | 2013-09-16 | 2018-01-24 | Agfa Nv | Composiciones curables por radiación para envases alimentarios |
| WO2015140541A1 (en) * | 2014-03-20 | 2015-09-24 | Fujifilm Speciality Ink Systems Limited | Printing ink |
| CN104650646A (zh) * | 2015-03-12 | 2015-05-27 | 山东德创喷墨科技有限公司 | 一种低迁移uv柔版油墨及其制备方法 |
| JP6477113B2 (ja) * | 2015-03-25 | 2019-03-06 | 東洋インキＳｃホールディングス株式会社 | 電子線硬化型インクジェットインキ |
| EP3289029B1 (en) | 2015-05-01 | 2022-02-23 | Sun Chemical Corporation | Electrically-insulating energy curable ink or coating composition |
| WO2017055203A1 (fr) * | 2015-09-28 | 2017-04-06 | MGI Digital Technology | Composition de vernis a faible migration pour substrat imprime par jet d'encre |
| EP3156461B1 (en) | 2015-10-13 | 2020-04-01 | Agfa Nv | Uv curable inkjet inks |
| EP3156463B1 (en) | 2015-10-13 | 2019-12-18 | Agfa Nv | Uv curable inkjet inks |
| EP3173249A1 (en) | 2015-11-30 | 2017-05-31 | Agfa-Gevaert | Laser markable compositions and methods to manufacture a packaging therewith |
| EP3445826B1 (en) | 2016-04-21 | 2021-07-14 | Flint Group Germany GmbH | Radiation curable ink formulation |
| EP3321330B1 (en) * | 2016-11-10 | 2022-01-05 | Agfa-Gevaert Nv | Solder mask inkjet inks for manufacturing printed circuit boards |
| KR101798450B1 (ko) * | 2017-01-10 | 2017-11-16 | 동우 화인켐 주식회사 | 광경화성 조성물 및 이로부터 형성된 광경화 막 |
| US10682837B2 (en) * | 2017-06-09 | 2020-06-16 | The Proctor & Gamble Company | Method and compositions for applying a material onto articles |
| PL422390A1 (pl) * | 2017-07-31 | 2019-02-11 | Cyfrowa Foto Spółka Z Ograniczoną Odpowiedzialnością | Sposób pokrywania lakierem UV zadrukowanych w technice cyfrowej kart wydruku fotograficznego zwiększających jego kontrastowość |
| CN111512452B (zh) * | 2017-10-17 | 2023-11-21 | 科迪华公司 | 用于显示装置的具有高量子点浓度的油墨组合物 |
| US11053400B2 (en) | 2018-07-13 | 2021-07-06 | Sun Chemical Corporation | Electron beam-curable compositions comprising poly(alkoxylates) |
| WO2020012157A1 (en) | 2018-07-13 | 2020-01-16 | Sun Chemical Corporation | Electron beam curable compositions comprising polyols |
| WO2020053543A1 (en) | 2018-09-10 | 2020-03-19 | Sun Chemical Corporation | Energy curable compositions comprising reaction products of poly(alkylene oxide)-containing glycidyl ethers and acrylic acid |
| CN112996867A (zh) * | 2018-11-20 | 2021-06-18 | 爱克发-格法特公司 | 用于制造印刷电路板的可辐射固化的喷墨油墨 |
| CN114008149B (zh) * | 2019-04-08 | 2023-08-18 | 艾利丹尼森公司 | 低迁移率uv-led固化性油墨制剂 |
| WO2022106853A1 (en) * | 2020-11-23 | 2022-05-27 | Sun Chemical Corporation | A uv printing process |
| CN112759979A (zh) * | 2021-02-24 | 2021-05-07 | 赵宝元 | 一种喷墨印刷的光固化光油墨水及其制备方法 |
| CN113150614A (zh) * | 2021-05-28 | 2021-07-23 | 南京玖泰新材料科技有限公司 | 一种可辐射固化喷墨流体、喷涂油墨及其用途 |
| CN114015013B (zh) * | 2021-11-16 | 2023-11-21 | 广东城首新材料有限公司 | 一种耐黄变自消色uv树脂及其在uv滴胶中的应用 |
| CN116640478B (zh) * | 2023-01-18 | 2025-02-11 | 乐凯华光印刷科技有限公司 | 一种含有杂化不饱和键单体的uv喷墨墨水及其制备方法 |
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| US6310115B1 (en) | 1998-10-29 | 2001-10-30 | Agfa-Gevaert | Ink compositions for ink jet printing |
| US6767980B2 (en) | 2002-04-19 | 2004-07-27 | Nippon Shokubai Co., Ltd. | Reactive diluent and curable resin composition |
| KR100738275B1 (ko) * | 2002-04-22 | 2007-07-12 | 가부시키가이샤 닛폰 쇼쿠바이 | 반응성 희석제 조성물 및 경화성 수지 조성물 |
| JP2005248007A (ja) * | 2004-03-04 | 2005-09-15 | Konica Minolta Holdings Inc | インクジェットインク及びインクジェット記録方法 |
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| EP1616921B1 (en) | 2004-07-15 | 2007-10-31 | Agfa Graphics N.V. | Novel radiation curable compositions |
| JP2008507598A (ja) * | 2004-07-16 | 2008-03-13 | ヘキソン スペシャルティ ケミカルズ インコーポレーテッド | 放射線硬化性インクジェットインク、その製造方法及びその使用方法 |
| US20100105795A1 (en) * | 2005-02-01 | 2010-04-29 | Henkel Corporation | Liquid Stable Thiol-Acrylate/Vinyl Ether Compositions |
| US20080045618A1 (en) | 2006-06-27 | 2008-02-21 | Nagvekar Devdatt S | Low viscosity UV curable ink formulations |
| EP2740773B2 (en) | 2006-10-11 | 2022-10-05 | Agfa Nv | Curable pigment inkjet ink sets and methods for preparing the said ink sets |
| EP2074162B1 (en) * | 2006-10-11 | 2018-04-25 | Kao Corporation | Radiation curable and jettable ink compositions |
| PL1935652T3 (pl) | 2006-12-21 | 2010-09-30 | Agfa Nv | Sposób drukowania strumieniowego i zestawy tuszów |
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| EP2065362A1 (en) | 2007-11-29 | 2009-06-03 | Agfa Graphics N.V. | Preparation method of copolymerizable photoinitiators |
| PL2130817T3 (pl) | 2008-06-05 | 2016-06-30 | Agfa Graphics Nv | Polimeryzowalne fotoinicjatory typu ii oraz kompozycje utwardzalne |
| EP2161264B1 (en) | 2008-09-09 | 2019-11-27 | Agfa Nv | Polymerizable photoinitiators and radiation curable compositions |
| EP2199273B1 (en) | 2008-12-18 | 2018-02-21 | Agfa Nv | Polymerizable photoinitiators and radiation curable compositions |
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| AU2010330040B2 (en) | 2009-12-07 | 2013-12-19 | Agfa Nv | UV-LED curable compositions and inks |
| EP2444429B1 (en) | 2010-10-20 | 2016-09-07 | Agfa Graphics N.V. | Led curable compositions |
| EP2826824B1 (en) * | 2012-06-06 | 2016-08-17 | Agfa Graphics Nv | Radiation curable inkjet inks and industrial inkjet printing methods |
| ES2547911T3 (es) * | 2012-07-06 | 2015-10-09 | Agfa Graphics Nv | Métodos de barnizado por inyección de tinta |
-
2012
- 2012-08-31 EP EP12182522.8A patent/EP2703457B1/en active Active
- 2012-08-31 ES ES12182522.8T patent/ES2671356T3/es active Active
-
2013
- 2013-08-13 CA CA2878524A patent/CA2878524A1/en not_active Abandoned
- 2013-08-13 BR BR112015003222A patent/BR112015003222A2/pt not_active IP Right Cessation
- 2013-08-13 IN IN10808DEN2014 patent/IN2014DN10808A/en unknown
- 2013-08-13 US US14/420,059 patent/US9701856B2/en active Active
- 2013-08-13 WO PCT/EP2013/066936 patent/WO2014032968A1/en active Application Filing
- 2013-08-13 AU AU2013307478A patent/AU2013307478B2/en not_active Ceased
- 2013-08-13 CN CN201380045192.1A patent/CN104583342B/zh active Active
Also Published As
| Publication number | Publication date |
|---|---|
| US9701856B2 (en) | 2017-07-11 |
| AU2013307478A1 (en) | 2015-01-22 |
| CN104583342B (zh) | 2017-07-11 |
| WO2014032968A1 (en) | 2014-03-06 |
| EP2703457A1 (en) | 2014-03-05 |
| IN2014DN10808A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 2015-09-04 |
| ES2671356T3 (es) | 2018-06-06 |
| CN104583342A (zh) | 2015-04-29 |
| CA2878524A1 (en) | 2014-03-06 |
| BR112015003222A2 (pt) | 2017-07-04 |
| EP2703457B1 (en) | 2018-03-07 |
| US20150203696A1 (en) | 2015-07-23 |
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| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |