JP6086791B2 - 結晶性スルホン化合物およびそれらの誘導体を含む相変化インク組成物 - Google Patents
結晶性スルホン化合物およびそれらの誘導体を含む相変化インク組成物 Download PDFInfo
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- JP6086791B2 JP6086791B2 JP2013085448A JP2013085448A JP6086791B2 JP 6086791 B2 JP6086791 B2 JP 6086791B2 JP 2013085448 A JP2013085448 A JP 2013085448A JP 2013085448 A JP2013085448 A JP 2013085448A JP 6086791 B2 JP6086791 B2 JP 6086791B2
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- phase change
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- sulfone
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- 125000003118 aryl group Chemical group 0.000 claims description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims description 32
- 238000002425 crystallisation Methods 0.000 claims description 26
- 230000008025 crystallization Effects 0.000 claims description 26
- 125000004122 cyclic group Chemical group 0.000 claims description 22
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 21
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Natural products OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 20
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 15
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- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical group OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 9
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
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- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 claims description 2
- GVETWQSIXZBHEP-UHFFFAOYSA-N 4-[4-hydroxy-2-(2-hydroxyphenyl)phenyl]sulfonyl-3-(2-hydroxyphenyl)phenol Chemical compound C=1C(O)=CC=C(S(=O)(=O)C=2C(=CC(O)=CC=2)C=2C(=CC=CC=2)O)C=1C1=CC=CC=C1O GVETWQSIXZBHEP-UHFFFAOYSA-N 0.000 claims description 2
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- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 claims description 2
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- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 claims description 2
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- 150000003899 tartaric acid esters Chemical class 0.000 claims 2
- JDHQUJOFJHVHEU-UHFFFAOYSA-N 1-(2-hydroxypropylsulfonyl)propan-2-ol Chemical compound CC(O)CS(=O)(=O)CC(C)O JDHQUJOFJHVHEU-UHFFFAOYSA-N 0.000 claims 1
- GPAPPPVRLPGFEQ-UHFFFAOYSA-N 4,4'-dichlorodiphenyl sulfone Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC=C(Cl)C=C1 GPAPPPVRLPGFEQ-UHFFFAOYSA-N 0.000 claims 1
- MZMGJAFJUYKKLI-UHFFFAOYSA-N chloro(methylsulfonyl)methane Chemical compound CS(=O)(=O)CCl MZMGJAFJUYKKLI-UHFFFAOYSA-N 0.000 claims 1
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 13
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- BEIOEBMXPVYLRY-UHFFFAOYSA-N [4-[4-bis(2,4-ditert-butylphenoxy)phosphanylphenyl]phenyl]-bis(2,4-ditert-butylphenoxy)phosphane Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(C=1C=CC(=CC=1)C=1C=CC(=CC=1)P(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C BEIOEBMXPVYLRY-UHFFFAOYSA-N 0.000 description 1
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- 239000000981 basic dye Chemical class 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- VHDKGFXLYYCBRN-QLGDYQOSSA-N bis(1-methyl-4-propan-2-ylcyclohexyl) (2R,3R)-2,3-dihydroxybutanedioate Chemical compound C(=O)(OC1(CCC(CC1)C(C)C)C)[C@H](O)[C@@H](O)C(=O)OC1(CCC(CC1)C(C)C)C VHDKGFXLYYCBRN-QLGDYQOSSA-N 0.000 description 1
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- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- IEEIDZAXDTVGGN-RMRYJAPISA-N cyclopenta-1,3-dien-1-yl(diphenyl)phosphane;(1s)-1-(2-diphenylphosphanylcyclopenta-1,3-dien-1-yl)-n,n-dimethylethanamine;iron(2+) Chemical compound [Fe+2].C1=C[CH-]C(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1[C@@H](N(C)C)C IEEIDZAXDTVGGN-RMRYJAPISA-N 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
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- 238000010017 direct printing Methods 0.000 description 1
- 239000000986 disperse dye Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
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- 230000005294 ferromagnetic effect Effects 0.000 description 1
- 239000011152 fibreglass Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000009499 grossing Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000011874 heated mixture Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
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- 229910010272 inorganic material Inorganic materials 0.000 description 1
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- 125000002346 iodo group Chemical group I* 0.000 description 1
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- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- NRZWYNLTFLDQQX-UHFFFAOYSA-N p-tert-Amylphenol Chemical compound CCC(C)(C)C1=CC=C(O)C=C1 NRZWYNLTFLDQQX-UHFFFAOYSA-N 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000012782 phase change material Substances 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 description 1
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- 239000004014 plasticizer Substances 0.000 description 1
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- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
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- IMFACGCPASFAPR-UHFFFAOYSA-O tributylazanium Chemical compound CCCC[NH+](CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-O 0.000 description 1
- 239000000984 vat dye Chemical class 0.000 description 1
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Classifications
-
- 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
- C09D11/34—Hot-melt 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M1/00—Inking and printing with a printer's forme
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Ink Jet (AREA)
- Ink Jet Recording Methods And Recording Media Thereof (AREA)
Description
以下の式Iのスルホン化合物である結晶性構成成分であって
非晶質化合物は、式IIの酒石酸エステルまたは式IIIのクエン酸エステルを含んでいてもよい
TROMは、偏光顕微鏡法(POM)を用いることによって結晶の外観および成長をモニターする。サンプルは、顕微鏡の直交偏光子間に置かれる。結晶性材料は、それらが複屈折であるために視覚可能である。光を通さない、例えばそれらの溶融状態のインクと同様の非晶質材料または液体は、POMの下では黒色に見える。故に、POMは、結晶性構成成分を見る場合に画像コントラストを可能にし、溶融状態から設定温度に冷却された場合に結晶性−非晶質インクの結晶化動力学を追跡できる。偏光顕微鏡法(POM)は、結晶性構成成分を見る場合に特別な画像コントラストを可能にする。
時間ゼロ(T=0s)−溶融サンプルは、顕微鏡の下で冷却段階に置かれる。
Tオンセット=第1の結晶が現れる時間
T成長=第1の結晶(Tオンセット)から結晶化終了までの結晶成長期間(T合計)
T合計=Tオンセット+T成長
インクの調製
米国特許出願整理番号13/095,795に示されるトリ−DL−メンチルシトレート(TMC)および米国特許出願整理番号13/095,784に示されるジ−DL−メンチルL−タートラート(DMT)を、インク配合物の非晶質構成成分として利用した。化合物1および非晶質材料は、染料を含まない(インクベースに関して)または2重量%のSolvebt Blue101染料(Keystone(Chicago,Illinois)から入手可能)と共に、130℃にて溶融状態で撹拌し、次いで冷却して、インクサンプルを得た。インクサンプルの結晶性/非晶質比は、重量%で約80/20または約70/30であった。2グラムのインクベースは、1.4グラムの化合物1および0.6グラムのTMCから配合した。4グラムの各インクサンプルを、3.14グラムの化合物1、0.78グラムの非晶質、および0.08グラムのSolvent Blue101または2.74グラムの化合物1、1.18グラムの非晶質、および0.08グラムのSolvent Blue101から配合した。結晶性および非晶質材料は、これらの混合比で非常に混和性であった。インク配合物の詳細を表3に示す。
図3は、ジフェニルスルホン(化合物1)/TMC/Solvent Blue101(68.6/29.4/2(重量%))を含む代表的なインクサンプルのDSCデータを示す。T溶融およびT結晶の両方が低温にシフトしたが、サンプルは依然として、非晶質構成成分および染料と混合された場合でもシャープな相転移を示した。迅速な結晶化は、時間分解光学顕微鏡法(TROM)測定によって確認した。
インクを、K−印刷プルーファー(RK Print Coat Instrument Ltd.,Litlington,Royston,Heris,SG80OZ,U.K.が製造)により、コーティングされた紙のXerox Digital Color Elite Gloss,120gsm(DCEG)でのK−プルーフプリント試験検査に使用した。垂直から約15°の角度にて湾曲した先端を有するスクラッチ/ゴージフィンガーを、528gの重りを適用して、約13mm/sの速度で画像にわたって引き寄せた場合。スクラッチ/ゴージ先端は、約12mmの曲率半径を有する旋盤円形ノーズ切削ビットに類似する。
本実施形態は、少なくとも1つの結晶性材料および少なくとも1つの非晶質材料を含有するインクジェット印刷について開発された堅牢性の相変化インク配合物を提供する。インクはまた、顔料または染料のような着色剤を含んでいてもよい。結晶性材料は、相変化インク組成物において結晶性構成成分として使用するために好適な特性を有することを示しており、非晶質材料と混和性である選択された結晶性スルホン化合物またはそれらの誘導体である。得られた結晶性材料は、堅牢性で迅速な印刷インクを提供する所望の物理的特性を有する。
Claims (18)
- 下記式Iで表されるスルホン化合物である結晶性構成成分と、
下記式IIで表される酒石酸エステル又は式IIIのクエン酸エステルを含む非晶質構成成分と、を含む相変化インク:
式I中、R6 及びR7は、同一でも異なっていてもよく、式中、R6 及びR7のそれぞれは、互いに独立に、(i)線状でも分岐状でも環状でも非環状でもよく、置換でも非置換でもよく、飽和アルキル基でも不飽和アルキル基でもよい、1〜40個の炭素原子を有するアルキル基であって、ここで前記アルキル基にはヘテロ原子が存在してもよい、アルキル基;(ii)置換アリールアルキル基でも非置換アリールアルキル基でもよい、4〜40個の炭素原子を有するアリールアルキル基であって、ここで前記アリールアルキル基のアルキル部分は、線状でも分岐状でも環状でも非環状でもよく、置換でも非置換でもよく、飽和でも不飽和でもよく、前記アリールアルキル基のアリール部分又はアルキル部分のいずれかにはヘテロ原子が存在してもよい、アリールアルキル基;及び(iii)置換芳香族基でも非置換芳香族基でもよい、3〜40個の炭素原子を有する芳香族基であって、ここで前記置換芳香族基における置換基は、線状、分岐状、環状又は非環状アルキル基であってもよく、前記芳香族基にはヘテロ原子が存在してもよい、芳香族基;並びにこれらの混合物からなる群から選択され、R 6 及びR 7 は、それらが結合するS原子と一緒に複素環式環を形成していてもよく;
式II及び式III中、R1、R2、R3、R4 及びR5は、それぞれ独立に、アルキル基(ここで前記アルキル基は、1〜40個の炭素原子を有し、直鎖でも分岐状でも環状でもよく、飽和でも不飽和でもよく、置換されていても置換されていなくてもよい)、置換若しくは非置換の芳香族基、置換若しくは非置換のヘテロ芳香族基、又はこれらの混合物である。 - 前記酒石酸エステルの酒石酸骨格がL−(+)−酒石酸、D−(−)−酒石酸、DL−酒石酸、又はメソ酒石酸、及びこれらの混合物から選択される、請求項1に記載の相変化インク。
- R6 及びR7のそれぞれが、独立に、1つ以上のハロ、アミノ、ヒドロキシ、シアノ又はこれらの組み合わせで置換されていてもよい、フェニル又はベンジルである、請求項1又は請求項2に記載の相変化インク。
- R6 及びR7のそれぞれが、独立に、1つ以上のヒドロキシル、シアノ又はこれらの組み合わせで置換された、メチル、エチル、イソプロピル、n−ブチル、又はビニルである、請求項1又は請求項2に記載の相変化インク。
- 前記結晶性構成成分が、前記相変化インクの総重量の60重量%〜95重量%の量で存在する、請求項1〜請求項4のいずれか一項に記載の相変化インク。
- 前記非晶質構成成分が、前記相変化インクの総重量の5重量%〜40重量%の量で存在する、請求項1〜請求項5のいずれか一項に記載の相変化インク。
- 染料、顔料、及びこれらの混合物からなる群より選択される着色剤をさらに含有する、請求項1〜請求項6のいずれか一項に記載の相変化インク。
- 前記結晶性構成成分が140℃の温度にて10cps未満の粘度を有する、請求項1〜請求項7のいずれか一項に記載の相変化インク。
- 前記結晶性構成成分の溶融温度が150℃未満である、請求項1〜請求項7のいずれか一項に記載の相変化インク。
- 前記結晶性構成成分の結晶化温度が60℃を超える、請求項1〜請求項9のいずれか一項に記載の相変化インク。
- 100℃〜140℃の噴出温度範囲にて1cps〜22cpsの粘度を有する、請求項1〜請求項7のいずれか一項に記載の相変化インク。
- 室温にて106cpsより高い粘度を有する、請求項1〜請求項11のいずれか一項に記載の相変化インク。
- 前記非晶質構成成分の重量に対する前記結晶性構成成分の重量の比(結晶性構成成分/非晶質構成成分)が、60/40〜95/5である、請求項1〜請求項12のいずれか一項に記載の相変化インク。
- 前記式I中、R6 及びR7のそれぞれは、独立に、1つ以上のハロ、アミノ、ヒドロキシ、又はシアノ基及びこれらの組み合わせで置換されていてもよい、アルキル又はアリールである、請求項1又は請求項2に記載の相変化インク。
- 前記結晶性構成成分が、ジフェニルスルホン、ジメチルスルホン、ビス(4−ヒドロキシフェニル)スルホン、ビス(4−アミノフェニル)スルホン、ビス(3−アミノフェニル)スルホン、ビス(4−クロロフェニル)スルホン、ビス(4−フルオロフェニル)スルホン、2−ヒドロキシフェニル−4−ヒドロキシフェニルスルホン、フェニル−4−クロロフェニルスルホン、フェニル−2−アミノフェニルスルホン、ビス(3−アミノ−4−ヒドロキシフェニル)スルホン、ジベンジルスルホン、メチルエチルスルホン、ジエチルスルホン、メチルイソプロピルスルホン、エチルイソプロピルスルホン、ジ−n−ブチルスルホン、ジビニルスルホン、メチル−2−ヒドロキシエチルスルホン、メチルクロロメチルスルホン、スルホラン、3−スルホレン、及びこれらの混合物からなる群から選択される、請求項1又は請求項2に記載の相変化インク。
- 室温で固体状態である、請求項1〜請求項15のいずか一項に記載の相変化インク。
- 噴出温度範囲が100℃〜140℃である、請求項1〜請求項16のいずれか一項に記載の相変化インク。
- 前記非晶質構成成分及び前記結晶性構成成分は液体状態で互いに混和性である、請求項1〜請求項17のいずれか一項に記載の相変化インク。
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US13/457,323 US8814999B2 (en) | 2012-04-26 | 2012-04-26 | Phase change ink compositions comprising crystalline sulfone compounds and derivatives thereof |
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KR20130131240A (ko) * | 2012-05-23 | 2013-12-03 | 주식회사 엘지화학 | 상변이 잉크 조성물 및 이를 이용한 전도성 패턴 |
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JP6895119B2 (ja) * | 2016-09-30 | 2021-06-30 | セイコーエプソン株式会社 | インクジェットインク組成物 |
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US20130284062A1 (en) | 2013-10-31 |
CA2813480C (en) | 2019-02-12 |
JP2013227568A (ja) | 2013-11-07 |
CA2813480A1 (en) | 2013-10-26 |
KR101931389B1 (ko) | 2018-12-20 |
US8814999B2 (en) | 2014-08-26 |
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