JP6603714B2 - くし形ポリウレタン分散剤 - Google Patents
くし形ポリウレタン分散剤 Download PDFInfo
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- JP6603714B2 JP6603714B2 JP2017522945A JP2017522945A JP6603714B2 JP 6603714 B2 JP6603714 B2 JP 6603714B2 JP 2017522945 A JP2017522945 A JP 2017522945A JP 2017522945 A JP2017522945 A JP 2017522945A JP 6603714 B2 JP6603714 B2 JP 6603714B2
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- Japan
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- polyurethane
- pigment
- pigments
- dispersant
- molecular weight
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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
- C09D11/102—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions other than those only involving unsaturated carbon-to-carbon bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3819—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen
- C08G18/3823—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing -N-C=O groups
- C08G18/3825—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing -N-C=O groups containing amide groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/50—Polyethers having heteroatoms other than oxygen
- C08G18/5021—Polyethers having heteroatoms other than oxygen having nitrogen
- C08G18/5036—Polyethers having heteroatoms other than oxygen having nitrogen containing -N-C=O groups
- C08G18/5039—Polyethers having heteroatoms other than oxygen having nitrogen containing -N-C=O groups containing amide groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
- C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
- C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
- C08G18/7671—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups containing only one alkylene bisphenyl group
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
- C08K3/013—Fillers, pigments or reinforcing additives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0041—Optical brightening agents, organic pigments
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
-
- 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
- C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
-
- 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
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
- C09D175/08—Polyurethanes from polyethers
-
- 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
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/45—Anti-settling agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Wood Science & Technology (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Polyurethanes Or Polyureas (AREA)
- Paints Or Removers (AREA)
Description
本出願の目的で、重量平均分子量を
る。1つの態様における分散剤はくし形ポリウレタンである。典型的なくし形ポリウレタンは、オキサミドジオール基を含有するポリウレタンである。本明細書に教示する如き分散剤を用いると、高い顔料充填率を有しかつ通常有益な粘度の範囲内に存在する幅広く多様なインクおよびコーティングを調製することが可能になる。
R2は水素原子または炭素数が1から8のアルキル基である。1つの態様における二官能アミノアルコールはジエタノールアミン(DEA)で6員ラクトンは4−ヒドロキシエチル−2,3−モルホリンジオン(HEMD)であり、そしてその反応を以下に示す:
Rは、エチレンオキサイド(EO)および/またはプロピレンオキサイド(PO)を炭素原子数が様々なアルコールに付加させることで生じさせたものである。いくつかの態様では、アミン基を有する分子の末端にPOブロックを付加させる。この上に記述したように、Rを下記の構造で表すことができ、
yはyとzの合計の5%から95%であり得そしてzはyとzの合計の5%から95%であり得る。HEMDとアミンからオキサミドジオールへの変換率は少なくとも90%、例えば約90%から約95%であり得る。
チタン、クロム酸塩、硫化物および酸化鉄である。有機顔料の代表的な例は、アゾ顔料[例えばアゾレーキ、不溶アゾ顔料、縮合アゾ顔料、キレートアゾ顔料、モノアゾ顔料(モノアリリド、B−ナフトール、ナフトールAS、ベンゾイミダゾロンおよび金属沈降アゾを包含)ばかりでなくジスアゾ顔料(ジアリリド、ジスアゾ縮合物、ジアゾピラゾイオンおよびビスアセトアセタリリドを包含)]、多環式顔料(例えばフタロシアニン顔料、ペリレン、ペリレンおよびペリノン顔料、アントラキノン顔料、キナクリドン顔料、ジオキサジン顔料、チオインジゴ顔料、イソインドリノン顔料およびキノフタロン顔料)、レーキ顔料(例えば塩基染料レーキおよび酸染料レーキ)、ニトロ顔料、ニトロソ顔料およびアニリンブラック昼光蛍光顔料である。他の代表的顔料には、イソインドリン、イソインドリノン、インジゴイド、ジケトピロロピロール、トリアリールカルボニウム、金属錯体、パール、液晶顔料、蛍光体および上述した顔料の機能的誘導体が含まれる。加うるに、適切な顔料には、水相中に分散させた顔料または表面が界面活性剤または高分子量分散剤で処理された顔料(例えば黒鉛炭素)も含まれる。
マレイン酸、マレイン酸の半エステル、シトラコン酸、イタコン酸およびそれらの組み合わせから成る群より選択する。代替態様では、グラインド樹脂と顔料分散液を同じにする。この場合、追加的量の顔料分散液をグラインド樹脂として作用させる。
HEMDが完全に溶解し、設定温度を高くした。その混合物が115℃に到達した時点でその混合物をその温度に約2時間維持しながら窒素下で撹拌した。次に、生成物を室温に冷却した。最終的生成物であるオキサミドジオールは室温で無色透明な液体である。3種類の実験を行い、反応体の使用量を以下の表1に示す:
Claims (9)
- ポリウレタンを含有して成る分散剤であって、
前記ポリウレタンが構造:
を有する、分散剤。 - 前記ポリウレタンが構造:
を有する請求項1記載の分散剤。 - ジイソシアネートとオキサミドジオールの反応で生じたポリウレタンを含有して成る分散剤であって、
前記ポリウレタンが構造:
を有する、分散剤。 - 前記ジイソシアネートが芳香族、脂肪族または脂環式である請求項3記載の分散剤。
- 前記ジイソシアネートがメチレンジフェニルジイソシアネートである請求項4記載の分散剤。
- 前記ポリウレタンが構造:
を有する請求項3記載の分散剤。 - 組成物であって、
顔料成分、および
ポリウレタンを含有する分散剤、
を含有して成り、
前記ポリウレタンが構造:
を有する、組成物。 - 前記顔料成分がフタロシアニン、カーボンブラック、酸化チタン、クロム酸塩、硫化物、酸化鉄、アゾレーキ、不溶アゾ顔料、縮合アゾ顔料、キレートアゾ顔料、モノアゾ顔料、モノアリリド、B−ナフトール、ナフトールAS、ベンゾイミダゾロン、金属沈降アゾ、ジスアゾ顔料、ジアリリド、ジスアゾ縮合物、ジアゾピラゾイオン、ビスアセトアセタリリド、フタロシアニン顔料、ペリレン、ペリノン顔料、アントラキノン顔料、キナクリドン顔料、ジオキサジン顔料、チオインジゴ顔料、イソインドリノン顔料、キノフタロン顔料、塩基染料レーキ、酸染料レーキ、ニトロ顔料、ニトロソ顔料、アニリンブラック昼光蛍光顔料、黒鉛炭素、イソインドリン、イソインドリノン、インジゴイド、ジケトピロロピロール、トリアリールカルボニウム、金属錯体、パール、液晶顔料、蛍光体、それらの機能的誘導体およびそれらの組み合わせから成る群より選択される請求項7記載の組成物。
- 前記ポリウレタンが構造:
を有する請求項7記載の組成物。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201462079660P | 2014-11-14 | 2014-11-14 | |
US62/079,660 | 2014-11-14 | ||
PCT/US2015/059236 WO2016077147A1 (en) | 2014-11-14 | 2015-11-05 | Comb polyurethane dispersants |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2018504259A JP2018504259A (ja) | 2018-02-15 |
JP6603714B2 true JP6603714B2 (ja) | 2019-11-06 |
Family
ID=55954878
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2017522945A Active JP6603714B2 (ja) | 2014-11-14 | 2015-11-05 | くし形ポリウレタン分散剤 |
Country Status (8)
Country | Link |
---|---|
US (1) | US10301489B2 (ja) |
EP (1) | EP3218423B1 (ja) |
JP (1) | JP6603714B2 (ja) |
KR (1) | KR102465005B1 (ja) |
CN (1) | CN107075106B (ja) |
BR (1) | BR112017008202B1 (ja) |
MX (1) | MX2017006176A (ja) |
WO (1) | WO2016077147A1 (ja) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US10106639B2 (en) * | 2016-09-16 | 2018-10-23 | Riso Kagaku Corporation | Oil-based inkjet ink |
US10793667B2 (en) | 2019-02-07 | 2020-10-06 | Covestro Deutschland Ag | Curable compositions, products and articles formed therefrom, and methods of forming the same |
CN112778485A (zh) * | 2021-02-08 | 2021-05-11 | 杭州临安科达环境科技研究所 | 一种梳型聚氨酯超分散剂的制备方法、分散剂及其应用 |
CN113201233B (zh) * | 2021-04-29 | 2022-07-01 | 宁波中苑颜料有限公司 | 一种光致变色有机颜料及其制备方法 |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE654667A (ja) * | 1963-10-22 | |||
EP0274756B1 (en) * | 1987-01-09 | 1990-10-31 | Nippon Oil Co., Ltd. | Urea-urethane grease composition |
US5852123A (en) | 1996-10-17 | 1998-12-22 | E. I. Du Pont De Nemours And Company | Graft copolymer with a urea or imid functional group as a pigment dispersant |
GB0311121D0 (en) * | 2003-05-15 | 2003-06-18 | Avecia Ltd | Polyurethane dispersants |
US9238766B2 (en) | 2004-05-13 | 2016-01-19 | Huntsman Petrochemical Llc | Comb-like polyetheralkanolamines in inks and coatings |
WO2014153046A2 (en) * | 2013-03-14 | 2014-09-25 | Ppg Industries Ohio, Inc. | Polyurethanes, articles and coatings prepared therefrom and methods of making the same |
US9464169B2 (en) * | 2004-09-01 | 2016-10-11 | Ppg Industries Ohio, Inc. | Polyurethanes, articles and coatings prepared therefrom and methods of making the same |
US9598527B2 (en) * | 2004-09-01 | 2017-03-21 | Ppg Industries Ohio, Inc. | Polyurethanes, articles and coatings prepared therefrom and methods of making the same |
DE102007038041A1 (de) * | 2007-08-10 | 2009-02-12 | Kronotec Ag | Verfahren zur Vermeidung der Emission von Aldehyden und flüchtigen organischen Verbindungen aus Holzwerkstoffen |
JP5771146B2 (ja) | 2008-09-18 | 2015-08-26 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | 改善された晶出挙動を有するポリエステルジオール系ポリウレタン |
-
2015
- 2015-11-05 MX MX2017006176A patent/MX2017006176A/es unknown
- 2015-11-05 KR KR1020177015934A patent/KR102465005B1/ko active IP Right Grant
- 2015-11-05 EP EP15858847.5A patent/EP3218423B1/en active Active
- 2015-11-05 CN CN201580056486.3A patent/CN107075106B/zh active Active
- 2015-11-05 WO PCT/US2015/059236 patent/WO2016077147A1/en active Application Filing
- 2015-11-05 US US15/518,520 patent/US10301489B2/en active Active
- 2015-11-05 BR BR112017008202-0A patent/BR112017008202B1/pt active IP Right Grant
- 2015-11-05 JP JP2017522945A patent/JP6603714B2/ja active Active
Also Published As
Publication number | Publication date |
---|---|
US10301489B2 (en) | 2019-05-28 |
KR102465005B1 (ko) | 2022-11-09 |
EP3218423A1 (en) | 2017-09-20 |
EP3218423A4 (en) | 2018-06-20 |
CN107075106B (zh) | 2020-01-21 |
JP2018504259A (ja) | 2018-02-15 |
EP3218423B1 (en) | 2021-01-06 |
WO2016077147A1 (en) | 2016-05-19 |
MX2017006176A (es) | 2017-07-31 |
US20170240756A1 (en) | 2017-08-24 |
BR112017008202B1 (pt) | 2021-11-03 |
CN107075106A (zh) | 2017-08-18 |
KR20170083603A (ko) | 2017-07-18 |
BR112017008202A2 (pt) | 2017-12-26 |
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