JP6280448B2 - 改善された画像堅牢性のためにポリエステルを含有する相変化インク - Google Patents
改善された画像堅牢性のためにポリエステルを含有する相変化インク Download PDFInfo
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- JP6280448B2 JP6280448B2 JP2014112165A JP2014112165A JP6280448B2 JP 6280448 B2 JP6280448 B2 JP 6280448B2 JP 2014112165 A JP2014112165 A JP 2014112165A JP 2014112165 A JP2014112165 A JP 2014112165A JP 6280448 B2 JP6280448 B2 JP 6280448B2
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- acid
- polyester
- ink
- phase change
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- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical class OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 19
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- 125000004432 carbon atom Chemical group C* 0.000 description 13
- 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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- 125000001072 heteroaryl group Chemical group 0.000 description 8
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- MHIBEGOZTWERHF-UHFFFAOYSA-N heptane-1,1-diol Chemical compound CCCCCCC(O)O MHIBEGOZTWERHF-UHFFFAOYSA-N 0.000 description 1
- SXCBDZAEHILGLM-UHFFFAOYSA-N heptane-1,7-diol Chemical compound OCCCCCCCO SXCBDZAEHILGLM-UHFFFAOYSA-N 0.000 description 1
- 230000003116 impacting effect Effects 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- HNEGQIOMVPPMNR-NSCUHMNNSA-N mesaconic acid Chemical compound OC(=O)C(/C)=C/C(O)=O HNEGQIOMVPPMNR-NSCUHMNNSA-N 0.000 description 1
- HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 1
- 239000008601 oleoresin Substances 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000011049 pearl Substances 0.000 description 1
- UWJJYHHHVWZFEP-UHFFFAOYSA-N pentane-1,1-diol Chemical compound CCCCC(O)O UWJJYHHHVWZFEP-UHFFFAOYSA-N 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 238000012643 polycondensation polymerization Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000992 solvent dye Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- MBDNRNMVTZADMQ-UHFFFAOYSA-N sulfolene Chemical compound O=S1(=O)CC=CC1 MBDNRNMVTZADMQ-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003899 tartaric acid esters Chemical class 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- ODBLHEXUDAPZAU-UHFFFAOYSA-N threo-D-isocitric acid Natural products OC(=O)C(O)C(C(O)=O)CC(O)=O ODBLHEXUDAPZAU-UHFFFAOYSA-N 0.000 description 1
- MAZWDMBCPDUFDJ-UHFFFAOYSA-N trans-Traumatinsaeure Natural products OC(=O)CCCCCCCCC=CC(O)=O MAZWDMBCPDUFDJ-UHFFFAOYSA-N 0.000 description 1
- GTZCVFVGUGFEME-UHFFFAOYSA-N trans-aconitic acid Natural products OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- MAZWDMBCPDUFDJ-VQHVLOKHSA-N traumatic acid Chemical compound OC(=O)CCCCCCCC\C=C\C(O)=O MAZWDMBCPDUFDJ-VQHVLOKHSA-N 0.000 description 1
- 150000005691 triesters Chemical class 0.000 description 1
- 229960004441 tyrosine Drugs 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41J—TYPEWRITERS; SELECTIVE PRINTING MECHANISMS, i.e. MECHANISMS PRINTING OTHERWISE THAN FROM A FORME; CORRECTION OF TYPOGRAPHICAL ERRORS
- B41J2/00—Typewriters or selective printing mechanisms characterised by the printing or marking process for which they are designed
- B41J2/005—Typewriters or selective printing mechanisms characterised by the printing or marking process for which they are designed characterised by bringing liquid or particles selectively into contact with a printing material
- B41J2/01—Ink jet
- B41J2/17—Ink jet characterised by ink handling
- B41J2/175—Ink supply systems ; Circuit parts therefor
- B41J2/17593—Supplying ink in a solid state
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41J—TYPEWRITERS; SELECTIVE PRINTING MECHANISMS, i.e. MECHANISMS PRINTING OTHERWISE THAN FROM A FORME; CORRECTION OF TYPOGRAPHICAL ERRORS
- B41J2/00—Typewriters or selective printing mechanisms characterised by the printing or marking process for which they are designed
- B41J2/005—Typewriters or selective printing mechanisms characterised by the printing or marking process for which they are designed characterised by bringing liquid or particles selectively into contact with a printing material
- B41J2/01—Ink jet
- B41J2/21—Ink jet for multi-colour printing
- B41J2/2107—Ink jet for multi-colour printing characterised by the ink properties
-
- 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
- C09D11/102—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions other than those only involving unsaturated carbon-to-carbon bonds
- C09D11/104—Polyesters
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)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Ink Jet (AREA)
- Ink Jet Recording Methods And Recording Media Thereof (AREA)
Description
R’は、アルキレン基である;
R’に隣接するすべてのカルボニル炭素は、2つの原子が単結合によって分離される場合に、少なくとも2つの原子によって分離される;または
R’に隣接するすべてのカルボニル炭素は、連続して共有連結された少なくとも3つの原子によって分離される;
mは、1〜1,000であり;および
nは、1〜1,000である。
バイオ系ポリエステル樹脂を、表1に記載されるような構成成分を有するように調製した。機械的撹拌機、ボトムドレインバルブおよび蒸留装置を備えた1リットルのParr反応器に、より少量のモノマー性樹脂酸およびロジン由来の中性材料と共にロジンから誘導されるダイマー酸を主に含む二量化ロジンであるDymerex(登録商標)(Eastman Chemical Companyから入手可能)(244グラム、0.50モル、0.15当量(eq.))、Sigma−Aldrich(登録商標)から得られた1,2−プロピレングリコール(127グラム、1.667モル、0.50eq.;0.2eq.過剰)、Sigma−Aldrich(登録商標)から得られたナフタレンジカルボン酸(NDC)(98グラム、0.40モル、0.12eq.)、Sigma−Aldrich(登録商標)から得られた1,3−プロパンジオール(151グラム、0.667モル、0.20eq.)、City Chemicals LLCから得られたアゼライン酸(132グラム、0.70モル、0.21eq.)、続いて1.4グラムのFascat(登録商標)4100(Arkema,Inc.から入手可能)およびVertec(登録商標)AC422チタン触媒(Johnson Matthey Catalystsから市販)の両方を充填した。反応器は窒素で覆い、反応器の温度を撹拌しながら170℃に徐々に上昇させた(一旦固体は溶融した)。収集フラスコにおいてメタノールを連続的に収集しながら、この反応混合物を窒素下において200℃で16時間維持した。反応混合物を205℃に加熱し、低真空を適用した。真空をより高度な真空(<0.1Torr)に切り替えた。この時間の間、エチレングリコールを蒸留し、樹脂の軟化点が100℃に到達したときに、反応器温度を180℃に低下し、ロジンフマレート(Harima Chemical,Japanから入手可能なRosin−FA)24グラム、0.067モル、0.02eq.)の第2の部分を添加した。100.6℃の軟化点に到達するまでさらに5時間高真空下のまま、反応混合物の温度を230℃まで徐々に上昇させた。次いで温度を195℃に低下させ、ポリマーをポリテトラフルオロエチレン(Teflon(登録商標))製パンに放出した。バイオ系ポリエステル樹脂を、特徴付け、5.69のC/O[炭素と酸素との比]、86.5%のバイオマス含有量、100.6℃の軟化温度、13.2℃のオンセットガラス転移温度、10.9のA.V.[酸価]、2,378の分子数、および5,250の分子量を有することを決定した。
バイオ系ポリエステル樹脂の合成。ポリ(マンデル酸−co−乳酸)コポリマーを次のように調製した。250ミリリットルの丸底フラスコに、Sigma−Aldrich(登録商標)から得られたDL−マンデル酸(533mmol、0.40eq.、81.0グラム)およびSigma−Aldrich(登録商標)から得られた乳酸(800mmol、0.6eq.、72.1グラム)を充填した。フラスコは、オーバーヘッド撹拌機、加熱マントル、窒素ライン、冷却器およびディーンスタークトラップを備えていた。モノマー混合物を200℃に20時間加熱した。縮合重合中に水が形成し、それをトラップに収集した。軟化点が90℃に到達したら、ポリマーをフラスコから放出した。実施例3のバイオ系ポリエステル樹脂を、特徴付け、60%のバイオマス含有量、90.0℃の軟化温度、33.2℃のオンセットガラス転移温度、83.6のA.V.、1,276の分子数、および738の分子量を有することを決定した。
表4に示されるような配合を有する3つのインクを調製したが、これはジベンジルヘキサン−1,6−ジイルジカルバメート(ポリウレタン)と、以下の手順によって製造されるL−酒石酸/シクロヘキサノール/tert−ブチルシクロヘキサノール(TBCT)の誘導体とを含む。ディーンスタークトラップを備えた500ミリリットルフラスコにおいて、L−酒石酸(40.0グラム、267mmol)、シクロヘキサノール(26.7グラム、267mmol)、4−(tert−ブチル)シクロヘキサノール(41.6グラム、267mmol)、およびキシレン(体積:250ミリリットル)を添加して懸濁液を得た。p−トルエンスルホン酸一水和物(1.014グラム、5.33mmol)を添加し、混合物を還流させた(油浴にわたってアルミホイルでカバーした175℃の油浴温度)。5時間後、10.0ミリリットルの水を収集し(theo:9.6ミリリットル)、室温まで冷却した(わずかに褐色)。次いでこれを精製して、TBCT混合物を得た)。Clariantから得られたピグメントブルー(BG4)を含むシアン着色剤を、実施例1から3のバイオ系ポリエステルと共に分散した。インクを、ポリウレタンと、TBCT−シアン分散液および実施例1、2および3のバイオ系ポリエステルと混合することによって調製した。故に、加熱されたビーカー(140℃)に、ポリウレタン(オーブンで溶融)を添加した。撹拌しながら、ポリエステルを添加し、続いてTBCT中のシアン分散液を添加した。これを1時間撹拌し、次いで1μmの濾紙で濾過して、所望のインクを得た。
実施例7の比較インクを、ジステアリルテレフタレート(DST)(6.75グラム、67.5重量%)、L−酒石酸/シクロヘキサノール/tert−ブチルシクロヘキサノール(TBCT)の誘導体(1.91グラム、19.1重量%)、およびDST中のシアン顔料濃度(1.33グラム、DST中15重量%シアン顔料)を合わせ、140℃で1時間撹拌することによって調製した。
実施例8の比較インクを、ジベンジルヘキサン−1,6−ジイルジカルバメート(497.1グラム、76.5重量%)、ジ−DL−メンチルL−タートラート(DMT)(22.88グラム、3.52重量%)およびシアン顔料分散液(130グラム、DMTの10重量%シアン顔料)を合わせ、140℃に加熱し、30分間均質化することによって調製した。
実施例9の比較インクは、Oce(現在はCanonが所有)のOce ColorWave 600プリンター使用するためにToner Pearlsインクとして販売される市販の固体インクである。
A=インク実施例4
B=インク実施例5
C=インク実施例6
Claims (6)
- L−酒石酸/シクロヘキサノール/tert−ブチルシクロヘキサノールの誘導体を含む非晶質化合物;
ポリウレタンを含む結晶性化合物;
ポリエステルポリマーであって、約500〜約8,000の分子量および約1.0〜約8.0の多分散指数を有するポリエステルポリマー;
任意の相乗剤;
任意の分散剤;および
着色剤
を含み、
前記ポリエステルポリマーは、
二量化ロジン、1,2−プロピレングリコール、ナフタレンジカルボン酸、1,3−プロパンジオール、およびロジンアクリレートを構成成分として調製された第1ポリエステルと、
アビエチン酸、グリセロール、ロジン酸−ジオールモノマー、1,6ヘキサンジオール、およびイソフタル酸を構成成分として調製された第2ポリエステルと、
マンデル酸、および乳酸を構成成分として調製された第3ポリエステルと、
から選択される少なくとも1種である、相変化インク組成物。 - 前記ポリウレタンは、ジベンジルヘキサン−1,6−ジイルジカルバメートである、請求項1に記載の相変化インク組成物。
- (1)L−酒石酸/シクロヘキサノール/tert−ブチルシクロヘキサノールの誘導体を含む非晶質化合物;ポリウレタンを含む結晶性化合物;ポリエステルポリマー;任意の相乗剤;任意の分散剤および着色剤を含む相変化インク組成物をインクジェット印刷装置に組み込む工程であって、ここでこのポリエステルポリマーは、約500〜約8,000の分子量、および約1.0〜約8.0の多分散指数を有する工程;
(2)インクを溶融する工程;および
(3)溶融インクの液滴を、基材上に画像様パターンに放出させる工程を含み、
前記ポリエステルポリマーは、
二量化ロジン、1,2−プロピレングリコール、ナフタレンジカルボン酸、1,3−プロパンジオール、およびロジンアクリレートを構成成分として調製された第1ポリエステルと、
アビエチン酸、グリセロール、ロジン酸−ジオールモノマー、1,6ヘキサンジオール、およびイソフタル酸を構成成分として調製された第2ポリエステルと、
マンデル酸、および乳酸を構成成分として調製された第3ポリエステルと、
から選択される少なくとも1種である、プロセス。 - 前記ポリウレタンは、ジベンジルヘキサン−1,6−ジイルジカルバメートである、請求項3に記載のプロセス。
- L−酒石酸/シクロヘキサノール/tert−ブチルシクロヘキサノールの誘導体を含む非晶質化合物;ポリウレタンを含む結晶性化合物;ポリエステルポリマー;任意の相乗剤;任意の分散剤および着色剤を含む相変化インク組成物を含むインクジェットプリンターのスティックまたはペレットであって、ここでこのポリエステルは、約500〜約8,000の分子量、および約1.0〜約8.0の多分散指数を有し、
前記ポリエステルポリマーは、
二量化ロジン、1,2−プロピレングリコール、ナフタレンジカルボン酸、1,3−プロパンジオール、およびロジンアクリレートを構成成分として調製された第1ポリエステルと、
アビエチン酸、グリセロール、ロジン酸−ジオールモノマー、1,6ヘキサンジオール、およびイソフタル酸を構成成分として調製された第2ポリエステルと、
マンデル酸、および乳酸を構成成分として調製された第3ポリエステルと、
から選択される少なくとも1種である、スティックまたはペレット。 - 前記ポリウレタンは、ジベンジルヘキサン−1,6−ジイルジカルバメートである、請求項5に記載のスティックまたはペレット。
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US13/920,831 | 2013-06-18 |
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US9822267B1 (en) * | 2016-09-12 | 2017-11-21 | Xerox Corporation | Phase-change digital advanced lithographic imaging ink with polyester transfer additive |
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JP2023154904A (ja) * | 2022-04-08 | 2023-10-20 | ブラザー工業株式会社 | インクジェット記録用水性インク、定着剤、インクジェット記録方法、インクジェット記録装置、及びインク収容容器 |
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US4490731A (en) | 1982-11-22 | 1984-12-25 | Hewlett-Packard Company | Ink dispenser with "frozen" solid ink |
US4889560A (en) | 1988-08-03 | 1989-12-26 | Tektronix, Inc. | Phase change ink composition and phase change ink produced therefrom |
US4889761A (en) | 1988-08-25 | 1989-12-26 | Tektronix, Inc. | Substrates having a light-transmissive phase change ink printed thereon and methods for producing same |
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