JP2016199688A5 - - Google Patents
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- JP2016199688A5 JP2016199688A5 JP2015081059A JP2015081059A JP2016199688A5 JP 2016199688 A5 JP2016199688 A5 JP 2016199688A5 JP 2015081059 A JP2015081059 A JP 2015081059A JP 2015081059 A JP2015081059 A JP 2015081059A JP 2016199688 A5 JP2016199688 A5 JP 2016199688A5
- Authority
- JP
- Japan
- Prior art keywords
- solid image
- thioxanthone
- evaluation
- vinyl chloride
- examples
- 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.)
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- 239000007787 solid Substances 0.000 description 7
- 238000011156 evaluation Methods 0.000 description 5
- BZHJMEDXRYGGRV-UHFFFAOYSA-N vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 3
- 238000007641 inkjet printing Methods 0.000 description 3
- 230000001678 irradiating Effects 0.000 description 3
- VVBLNCFGVYUYGU-UHFFFAOYSA-N Michler's ketone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 2
- VMHYWKBKHMYRNF-UHFFFAOYSA-N (2-chlorophenyl)-phenylmethanone Chemical compound ClC1=CC=CC=C1C(=O)C1=CC=CC=C1 VMHYWKBKHMYRNF-UHFFFAOYSA-N 0.000 description 1
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 1
- BOCJQSFSGAZAPQ-UHFFFAOYSA-N 1-chloroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2Cl BOCJQSFSGAZAPQ-UHFFFAOYSA-N 0.000 description 1
- BTJPUDCSZVCXFQ-UHFFFAOYSA-N 2,4-diethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC(CC)=C3SC2=C1 BTJPUDCSZVCXFQ-UHFFFAOYSA-N 0.000 description 1
- XOGPDSATLSAZEK-UHFFFAOYSA-N 2-Aminoanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(N)=CC=C3C(=O)C2=C1 XOGPDSATLSAZEK-UHFFFAOYSA-N 0.000 description 1
- SJEBAWHUJDUKQK-UHFFFAOYSA-N 2-Ethylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC=C3C(=O)C2=C1 SJEBAWHUJDUKQK-UHFFFAOYSA-N 0.000 description 1
- ZCDADJXRUCOCJE-UHFFFAOYSA-N 2-chlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3SC2=C1 ZCDADJXRUCOCJE-UHFFFAOYSA-N 0.000 description 1
- MYISVPVWAQRUTL-UHFFFAOYSA-N 2-methylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC=C3SC2=C1 MYISVPVWAQRUTL-UHFFFAOYSA-N 0.000 description 1
- KTALPKYXQZGAEG-UHFFFAOYSA-N 2-propan-2-ylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C(C)C)=CC=C3SC2=C1 KTALPKYXQZGAEG-UHFFFAOYSA-N 0.000 description 1
- OKISUZLXOYGIFP-UHFFFAOYSA-N 4,4'-Dichlorobenzophenone Chemical compound C1=CC(Cl)=CC=C1C(=O)C1=CC=C(Cl)C=C1 OKISUZLXOYGIFP-UHFFFAOYSA-N 0.000 description 1
- IKVYHNPVKUNCJM-UHFFFAOYSA-N 4-propan-2-ylthioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C(C(C)C)=CC=C2 IKVYHNPVKUNCJM-UHFFFAOYSA-N 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N Benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- WXCOUECZNHUGFI-UHFFFAOYSA-N C(C1=CC=CC=C1)(=O)C1=CC=CC=C1.COC1=CC=C(C(=O)C2=CC=C(C=C2)N(C)C)C=C1 Chemical class C(C1=CC=CC=C1)(=O)C1=CC=CC=C1.COC1=CC=C(C(=O)C2=CC=C(C=C2)N(C)C)C=C1 WXCOUECZNHUGFI-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- LHMRXAIRPKSGDE-UHFFFAOYSA-N benzo[a]anthracene-7,12-dione Chemical compound C1=CC2=CC=CC=C2C2=C1C(=O)C1=CC=CC=C1C2=O LHMRXAIRPKSGDE-UHFFFAOYSA-N 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- VYHBFRJRBHMIQZ-UHFFFAOYSA-N bis[4-(diethylamino)phenyl]methanone Chemical compound C1=CC(N(CC)CC)=CC=C1C(=O)C1=CC=C(N(CC)CC)C=C1 VYHBFRJRBHMIQZ-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- -1 isopropoxycarbonyl chlorothioxanthone Chemical compound 0.000 description 1
Description
かかる光ラジカル重合開始剤としては、例えば下記化合物等の１種または２種以上が挙げられる。
ベンゾフェノン、ヒドロキシベンゾフェノン、２−クロロベンゾフェノン、４，４′−ジクロロベンゾフェノン、４，４′−ビスジエチルアミノベンゾフェノン、４，４′−ビスジメチルアミノベンゾフェノン（ミヒラーケトン）、４−メトキシ−４′−ジメチルアミノベンゾフェノン、特開２００８−２８０４２７号公報の一般式（１）で表されるベンゾフェノン化合物等のベンゾフェノン類またはその塩。
Examples of such radical photopolymerization initiators include one or more of the following compounds.
Benzophenone, hydroxybenzophenone, 2-chlorobenzophenone, 4,4'-dichlorobenzophenone, 4,4'-bisdiethylaminobenzophenone, 4,4'-bisdimethylaminobenzophenone (Michler ketone), 4-methoxy-4'-dimethylaminobenzophenone Benzophenones such as benzophenone compounds represented by the general formula (1) of JP 2008-280427 A or salts thereof.
チオキサントン、２−クロロチオキサントン、２−メチルチオキサントン、２−イソプロピルチオキサントン、２，４−ジエチルチオキサントン、４−イソプロピルチオキサントン、イソプロポキシクロロチオキサントン、特開２００８−２８０４２７号公報の一般式（２）で表されるチオキサントン化合物等のチオキサントン類またはその塩。
エチルアントラキノン、ベンズアントラキノン、アミノアントラキノン、クロロアントラキノン等のアントラキノン類。
Thioxanthone, 2-chlorothioxanthone, expressed in 2-methyl thioxanthone, 2-isopropyl thioxanthone, 2,4-diethyl thioxanthone, 4-isopropylthioxanthone, isopropoxycarbonyl chlorothioxanthone, formula of JP-2008-280427 (2) Thioxanthones such as thioxanthone compounds or salts thereof.
Anthraquinones such as ethyl anthraquinone, benzanthraquinone, aminoanthraquinone and chloroanthraquinone.
〈延伸性評価〉
上記各実施例、比較例で調製したインクジェットインクにより、熱成形が可能な軟質塩化ビニルフィルムの表面に、インクジェット印刷によってベタ画像を形成したのち、ＬＥＤランプ〔フォセオンテクノロジー（Ｐｈｏｓｅｏｎ Ｔｅｃｈｎｏｌｏｇｙ）社製のＦｉｒｅ ＪｅｔＦＪ２００〕を用いて、出力：８Ｗ、実測ピーク照度：７．２Ｗ／ｃｍ２、積算光量：２Ｊ／ｃｍ２の条件で紫外線を照射して上記ベタ画像を光硬化させた。
<Extension evaluation>
After forming a solid image by inkjet printing on the surface of a soft vinyl chloride film that can be thermoformed with the inkjet ink prepared in each of the above examples and comparative examples, an LED lamp (manufactured by Phoseon Technology) The solid image was photocured by irradiating ultraviolet rays under the conditions of output: 8 W, measured peak illuminance: 7.2 W / cm 2 , and integrated light amount: 2 J / cm 2 .
次いで、上記軟質塩化ビニルフィルムを１５０℃に加熱しながら一方向に延伸した際のベタ画像の状態を観察して、下記の基準で延伸性を評価した。
◎：延伸率４００％でもベタ画像にひひ割れは生じなかった。極めて良好。
○：延伸率４００％でひび割れを生じたが、３５０％ではひひ割れを生じなかった。良好。
×：延伸率３５０％でひび割れを生じた。不良。
Next, the state of the solid image when the soft vinyl chloride film was stretched in one direction while being heated to 150 ° C. was observed, and the stretchability was evaluated according to the following criteria.
A: No cracks occurred in the solid image even at a stretching ratio of 400%. Very good.
○: Cracks occurred at a stretching ratio of 400%, but no cracks occurred at 350%. Good.
X: Cracking occurred at a stretching ratio of 350%. Bad.
〈光硬化性評価〉
上記各実施例、比較例で調製したインクジェットインクにより、延伸性評価と同じ軟質塩化ビニルフィルムの表面に、インクジェット印刷によってベタ画像を形成したのち、同じＬＥＤランプを用いて、出力：８Ｗ、実測ピーク照度：７．２Ｗ／ｃｍ２、積算光量：１Ｊ／ｃｍ２の条件で紫外線を照射して上記ベタ画像を光硬化させた。
<Photocurability evaluation>
After forming a solid image by inkjet printing on the surface of the same soft vinyl chloride film as in the stretchability evaluation using the inkjet ink prepared in each of the above Examples and Comparative Examples, using the same LED lamp, output: 8 W, measured peak The solid image was photocured by irradiating with ultraviolet rays under the conditions of illuminance: 7.2 W / cm 2 and integrated light quantity: 1 J / cm 2 .
〈耐アルコール性評価)
上記各実施例、比較例で調製したインクジェットインクにより、延伸性評価と同じ軟質塩化ビニルフィルムの表面に、インクジェット印刷によってベタ画像を形成したのち、同じＬＥＤランプを用いて、出力：８Ｗ、実測ピーク照度：７．２Ｗ／ｃｍ２、積算光量：２Ｊ／ｃｍ２の条件で紫外線を照射して上記画像を光硬化させた。
<Alcohol resistance evaluation>
After forming a solid image by inkjet printing on the surface of the same soft vinyl chloride film as in the stretchability evaluation using the inkjet ink prepared in each of the above Examples and Comparative Examples, using the same LED lamp, output: 8 W, measured peak The image was photocured by irradiating with ultraviolet rays under the conditions of illuminance: 7.2 W / cm 2 and integrated light quantity: 2 J / cm 2 .
実施例１〜３、６、７と実施例５の結果より、波長域の狭いＬＥＤからの光に対する光硬化性をより一層向上するためには、単官能ラジカル重合性成分としてのＨＥＶＥとＡＣＭＯの質量比ＨＥＶＥ／ＡＣＭＯを３．０以下とするのが好ましいことが判った。
実施例１〜３、６、７と実施例８の結果より、画像の耐アルコール性をより一層向上するためには、単官能ラジカル重合性成分の割合を９５質量％以下とするのが好ましいことが判った。
From the results of Example 1～3,6,7 Example 5, in order to further improve the photocurable against the light from the narrow LED wavelength region, and HEVE the monofunctional radically polymerizable component It was found that the ACMO mass ratio HEVE / ACMO is preferably 3.0 or less.
From the results of Examples 1-3, 6, 7 and Example 8, in order to further improve the alcohol resistance of the image, it is preferable that the ratio of the monofunctional radically polymerizable component is 95% by mass or less. I understood.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2015081059A JP6476519B2 (en) | 2015-04-10 | 2015-04-10 | Inkjet ink |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2015081059A JP6476519B2 (en) | 2015-04-10 | 2015-04-10 | Inkjet ink |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016199688A JP2016199688A (en) | 2016-12-01 |
| JP2016199688A5 true JP2016199688A5 (en) | 2018-04-26 |
| JP6476519B2 JP6476519B2 (en) | 2019-03-06 |
Family
ID=57422340
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015081059A Active JP6476519B2 (en) | 2015-04-10 | 2015-04-10 | Inkjet ink |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP6476519B2 (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6747823B2 (en) | 2016-02-23 | 2020-08-26 | サカタインクス株式会社 | Photocurable ink composition for inkjet printing |
| JP6878080B2 (en) * | 2017-03-27 | 2021-05-26 | セーレン株式会社 | Inkjet ink and printed matter manufacturing method |
| JP6956549B2 (en) * | 2017-07-14 | 2021-11-02 | サカタインクス株式会社 | Photocurable inkjet printing ink composition |
| JP7425395B2 (en) * | 2019-02-08 | 2024-01-31 | セイコーエプソン株式会社 | Inkjet method and inkjet device |
| US20240117081A1 (en) * | 2019-11-14 | 2024-04-11 | Adeka Corporation | Polymerizable composition, vehicle, cured material, and method of manufacturing cured material |
| CN111978854A (en) * | 2020-09-03 | 2020-11-24 | 深圳市布瑞特水墨涂料有限公司 | Environment-friendly ultraviolet-curing fluff touch oil and preparation method thereof |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH10219158A (en) * | 1997-01-31 | 1998-08-18 | Teikoku Ink Seizo Kk | High-performance ink jet printing water-base ink |
| JP3461501B1 (en) * | 2002-06-10 | 2003-10-27 | 株式会社日本触媒 | Active energy ray-curable ink for inkjet printing |
| JP6335881B2 (en) * | 2013-03-28 | 2018-05-30 | セーレン株式会社 | Decorative film for insert molding and decorative insert molded product |
| JP2014198748A (en) * | 2013-03-29 | 2014-10-23 | 富士フイルム株式会社 | Ink composition for inkjet recording, image forming method, production method of molded product and molded product |
-
2015
- 2015-04-10 JP JP2015081059A patent/JP6476519B2/en active Active
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