JP2015004061A - カーマイン着色剤 - Google Patents
カーマイン着色剤 Download PDFInfo
- Publication number
- JP2015004061A JP2015004061A JP2014114446A JP2014114446A JP2015004061A JP 2015004061 A JP2015004061 A JP 2015004061A JP 2014114446 A JP2014114446 A JP 2014114446A JP 2014114446 A JP2014114446 A JP 2014114446A JP 2015004061 A JP2015004061 A JP 2015004061A
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- Prior art keywords
- acid
- carmine
- polymer
- polyester
- modified
- 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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- 235000012730 carminic acid Nutrition 0.000 title claims abstract description 94
- 239000003086 colorant Substances 0.000 title abstract description 13
- 229920000728 polyester Polymers 0.000 claims abstract description 33
- 229920000642 polymer Polymers 0.000 claims description 66
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 14
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 14
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 7
- KLDXJTOLSGUMSJ-JGWLITMVSA-N Isosorbide Chemical compound O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 KLDXJTOLSGUMSJ-JGWLITMVSA-N 0.000 claims description 5
- 229960002479 isosorbide Drugs 0.000 claims description 5
- 150000001735 carboxylic acids Chemical class 0.000 claims description 3
- 239000001384 succinic acid Substances 0.000 claims description 3
- 239000003153 chemical reaction reagent Substances 0.000 abstract description 20
- 229920005862 polyol Polymers 0.000 abstract description 16
- 150000003077 polyols Chemical class 0.000 abstract description 15
- 239000004106 carminic acid Substances 0.000 abstract description 11
- 229940114118 carminic acid Drugs 0.000 abstract description 6
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 abstract description 3
- UPVVMOJGGFCVCD-ATMKFHIZSA-N [C@H]1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)C1=C(C(=C2C(C=3C=C(CC(C3C(C2=C1O)=O)(C(=O)O)C)O)=O)O)O Chemical compound [C@H]1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)C1=C(C(=C2C(C=3C=C(CC(C3C(C2=C1O)=O)(C(=O)O)C)O)=O)O)O UPVVMOJGGFCVCD-ATMKFHIZSA-N 0.000 abstract description 2
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- DGQLVPJVXFOQEV-NGOCYOHBSA-N carminic acid Chemical compound OC1=C2C(=O)C=3C(C)=C(C(O)=O)C(O)=CC=3C(=O)C2=C(O)C(O)=C1[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O DGQLVPJVXFOQEV-NGOCYOHBSA-N 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- -1 alum Chemical class 0.000 description 10
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- 239000003054 catalyst Substances 0.000 description 9
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- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 8
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
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- 125000002843 carboxylic acid group Chemical group 0.000 description 6
- DGQLVPJVXFOQEV-JNVSTXMASA-N carminic acid Chemical compound OC1=C2C(=O)C=3C(C)=C(C(O)=O)C(O)=CC=3C(=O)C2=C(O)C(O)=C1[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O DGQLVPJVXFOQEV-JNVSTXMASA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
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- 238000005886 esterification reaction Methods 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
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- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
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- 238000004132 cross linking Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000003999 initiator Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
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- 238000003786 synthesis reaction Methods 0.000 description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical class OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 4
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
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- 235000011037 adipic acid Nutrition 0.000 description 4
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 4
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- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical group 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
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- 239000004645 polyester resin Substances 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 4
- PKYXMVZTROVMSE-UHFFFAOYSA-N 1,3-dihydroxypropane-2-sulfonic acid Chemical compound OCC(CO)S(O)(=O)=O PKYXMVZTROVMSE-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 238000007259 addition reaction Methods 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- LDCRTTXIJACKKU-ONEGZZNKSA-N dimethyl fumarate Chemical compound COC(=O)\C=C\C(=O)OC LDCRTTXIJACKKU-ONEGZZNKSA-N 0.000 description 3
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- 238000000034 method Methods 0.000 description 3
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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
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B61/00—Dyes of natural origin prepared from natural sources, e.g. vegetable sources
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/66—Polyesters containing oxygen in the form of ether groups
- C08G63/668—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/02—Hydroxy-anthraquinones; Ethers or esters thereof
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
- C09B69/109—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing other specific dyes
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyesters Or Polycarbonates (AREA)
- Developing Agents For Electrophotography (AREA)
Abstract
【解決手段】光安定性および熱安定性であり、耐酸化性であるカーマイン(7−α−D−グルコピラノシル−9,10−ジヒドロ−3,5,6,8−テトラヒドロキシ−1−メチル−9,10−ジオキソアントラセンカルボン酸であるカルミン酸のアルミニウム塩)をポリオール試薬としたポリエステル。
【選択図】なし
Description
250mlの丸底フラスコ(RBF)を、アゼライン酸(AA、44.7mmol、0.07当量、8.41g)、カーマイン(6.38mmol、0.01当量、3.14g)、コハク酸(SA,287mmol、0.45当量、33.9g)、イソソルビド(IS、300mmol、0.47当量、43.8g)および、ブチル(ヒドロキシル)スタナンオン(stannanone)触媒(6.38mmol、0.01当量、1.333g)で充填した。フラスコに、オーバーヘッドスターラー、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取り付けた。200℃(4時間)から215℃(3時間)で開始する温度の範囲にわたって、重合を行った。縮重合中に形成された水を、トラップに収集した。軟化点(Ts)が59.1℃に達した時点で、フラスコから、ポリマーを取り出した。樹脂のTsを、FP80 中央処理装置およびFP83 Dropping Cellからなる、Mettler FP800 Thermosystemにより測定した。目的のTsが達成されるまで、1℃/分で昇温するように、温度をプログラムした。
250mlのRBFを、AA(38.3mmol、0.06当量、7.21g)、カーマイン(5.11mmol、0.008当量、2.51g)、SA(295mmol、0.462当量、34.8g)、IS(300mmol、0.47当量、43.8g)および、ブチル(ヒドロキシル)スタナンオン(stannanone)触媒(6.38mmol、0.01当量、1.333g)で充填した。フラスコに、オーバーヘッドスターラー、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取り付けた。205℃(8時間)から215℃(3時間)で開始する温度の範囲にわたって、重合を行った。縮重合中に形成された水を、トラップに収集した。Tsが65.5℃に達した時点で、フラスコから、ポリマーを取り出した。
250mlのRBFを、1,9−ノナンジオール(400mmol、0.40当量、64.1g)、カーマイン(5.0mmol、0.005当量、2.46g)、SA(495mmol、0.495当量、58.5g)、IS(100mmol、0.10当量、14.61g)および、ブチル(ヒドロキシル)スタナンオン(stannanone)触媒(6.20mmol、0.0062当量、1.295g)で充填した。フラスコに、オーバーヘッドスターラー、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取り付けた。205℃(4時間)から215℃(15時間)で開始する温度の範囲にわたって、重合を行った。縮重合中に形成された水を、トラップに収集した。軟化点(Ts)が53.9℃に達した時点で、フラスコから、ポリマーを取り出した。
250mlのRBFを、1,9−ノナンジオール(278mmol、0.37当量、44.5g)、カーマイン(1.50mmol、0.002当量、0.739g)、SA(375mmol、0.50当量、44.3g)、IS(IS、96mmol、0.128当量、14.03g)および、ブチル(ヒドロキシル)スタナンオン(stannanone)触媒(3.75mmol、0.005当量、0.783g)で充填した。フラスコに、オーバーヘッドスターラー、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取り付けた。210℃(12時間)から215−220℃(10時間)で開始する温度の範囲にわたって、重合を行った。縮重合中に形成された水を、トラップに収集した。フラスコから、ポリマーを取り出した。
以下の表1に、カーマイン系ポリマーに関する分析データを示す。比較について、SA(0.415当量)、IS(0.488当量)およびAA(0.098当量)で製造されたコントロールのバイオポリマーの同じデータを、コントロールの低分子量の非晶性ポリエステル樹脂およびコントロールの高分子量樹脂と共に、表にさらに表す。実施例1〜4のカーマイン含有ポリマーにおける形状/構造は、ポリマーに、1,9−ノナンジオール(結晶)またはアゼライン酸(1,9−ノナン 2価酸、非晶質)のいずれかを含むことにより調整された。実施例3および4のポリマーは、融点に基づいて、結晶の特性を示す。
100mlのRBFを、カーマイン(5モル、0.5当量、2.462g)およびSA(50mmol、5当量、5.90g)で充填した。フラスコに、オーバーヘッドスターラー、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取り付けた。178℃、3時間で開始する温度の範囲にわたって、重合を行った。縮重合中に形成された水を、トラップに収集した。得られた材料は、更なる重縮合のためのマクロモノマーとして使用され得る。ペンダントヒドロキシル基にコハク酸を付加することにより、少しの柔軟性を提供するのに役立つ、カーマイン分子上より長いペンダント鎖、すなわち、フレキシブルスペーサーが提供される。
Claims (10)
- 修飾されたカーマイン。
- ポリマーを含む、請求項1記載の修飾されたカーマイン。
- 前記ポリマーが、ポリエステルを含む、請求項1記載の修飾されたカーマイン。
- 1つ以上の結合分子を含む、請求項1記載の修飾されたカーマイン。
- 前記結合分子が、カルボン酸またはポリカルボン酸を含む、請求項4記載の修飾されたカーマイン。
- 前記ポリカルボン酸が、コハク酸またはアゼライン酸を含む、請求項5記載の修飾されたカーマイン。
- 前記ポリエステルが、1つ以上のコハク酸、アゼライン酸およびイソソルビドを含む、請求項3記載の修飾されたカーマイン。
- カーマイン部分を含む、ポリエステルポリマー。
- 前記カーマイン部分が、前記ポリマーのペンダント基を含む、請求項8記載のポリエステルポリマー。
- コハク酸、アゼライン酸またはイソソルビドを含む、請求項8記載のポリエステルポリマー。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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US13/920,164 | 2013-06-18 | ||
US13/920,164 US10184024B2 (en) | 2013-06-18 | 2013-06-18 | Carmine colorants |
Publications (1)
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JP2015004061A true JP2015004061A (ja) | 2015-01-08 |
Family
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JP2014114446A Pending JP2015004061A (ja) | 2013-06-18 | 2014-06-02 | カーマイン着色剤 |
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US (1) | US10184024B2 (ja) |
JP (1) | JP2015004061A (ja) |
KR (1) | KR20140147013A (ja) |
CN (1) | CN104231243B (ja) |
CA (1) | CA2852325C (ja) |
DE (1) | DE102014210818A1 (ja) |
RU (1) | RU2664931C2 (ja) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
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FR3025797B1 (fr) | 2014-09-12 | 2018-03-02 | Arkema France | Resines polyesters hydroxyles ou carboxyles biosourcees. |
FR3025798B1 (fr) | 2014-09-12 | 2016-09-16 | Arkema France | Procede specifique de preparation de polyesters biosources. |
Citations (5)
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US3278486A (en) * | 1959-02-17 | 1966-10-11 | Scripto Inc | Colored polymeric materials |
JPS52146436A (en) * | 1976-06-01 | 1977-12-06 | Pola Kasei Kogyo Kk | Method of preparing pigments |
JP2012073304A (ja) * | 2010-09-28 | 2012-04-12 | Tomoegawa Paper Co Ltd | 電子写真用トナー |
JP2013082903A (ja) * | 2011-09-27 | 2013-05-09 | National Institute Of Advanced Industrial Science & Technology | ポリエステル樹脂の製造方法 |
JP2014520912A (ja) * | 2011-06-30 | 2014-08-25 | イー アンド ジェイ ガロ ワイネリイ | 天然結晶質着色剤および製造方法 |
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US4636261A (en) * | 1984-10-24 | 1987-01-13 | Heinze Richard F | Dry lake system |
US4804719A (en) * | 1988-02-05 | 1989-02-14 | Eastman Kodak Company | Water-dissipatable polyester and polyester-amides containing copolymerized colorants |
US5147673A (en) * | 1989-08-16 | 1992-09-15 | Jose Schul | Colorant based on carminic acid, method of preparation, and method of coloring a foodstuff |
US6818730B2 (en) * | 2002-04-26 | 2004-11-16 | E. I. Du Pont De Nemours And Company | Process to produce polyesters which incorporate isosorbide |
DE10219508A1 (de) * | 2002-04-30 | 2003-11-13 | Basf Ag | Verfahren zur Herstellung hochfunktioneller, hyperverzweigter Polyester |
RU2243981C1 (ru) * | 2003-09-03 | 2005-01-10 | Открытое акционерное общество "Лианозовский молочный комбинат" | Комплексное соединение карминовой кислоты, способ его получения, пищевой продукт и напиток, содержащие комплексное соединение карминовой кислоты |
US20060089421A1 (en) * | 2004-10-25 | 2006-04-27 | Sundar Vasudevan | Polymeric colorants having pigment and dye components and corresponding ink compositions |
US8163459B2 (en) * | 2010-03-01 | 2012-04-24 | Xerox Corporation | Bio-based amorphous polyester resins for emulsion aggregation toners |
JP5445418B2 (ja) * | 2010-09-24 | 2014-03-19 | 富士ゼロックス株式会社 | イエロートナー、現像剤、トナーカートリッジ、プロセスカートリッジ、画像形成装置及び画像形成方法 |
US9181389B2 (en) * | 2013-05-20 | 2015-11-10 | Xerox Corporation | Alizarin-based polymer colorants |
-
2013
- 2013-06-18 US US13/920,164 patent/US10184024B2/en active Active
-
2014
- 2014-05-21 CA CA2852325A patent/CA2852325C/en not_active Expired - Fee Related
- 2014-06-02 JP JP2014114446A patent/JP2015004061A/ja active Pending
- 2014-06-04 CN CN201410245863.5A patent/CN104231243B/zh not_active Expired - Fee Related
- 2014-06-05 DE DE102014210818.7A patent/DE102014210818A1/de not_active Withdrawn
- 2014-06-09 KR KR20140069156A patent/KR20140147013A/ko not_active Application Discontinuation
- 2014-06-17 RU RU2014124524A patent/RU2664931C2/ru active
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
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US3278486A (en) * | 1959-02-17 | 1966-10-11 | Scripto Inc | Colored polymeric materials |
JPS52146436A (en) * | 1976-06-01 | 1977-12-06 | Pola Kasei Kogyo Kk | Method of preparing pigments |
JP2012073304A (ja) * | 2010-09-28 | 2012-04-12 | Tomoegawa Paper Co Ltd | 電子写真用トナー |
JP2014520912A (ja) * | 2011-06-30 | 2014-08-25 | イー アンド ジェイ ガロ ワイネリイ | 天然結晶質着色剤および製造方法 |
JP2013082903A (ja) * | 2011-09-27 | 2013-05-09 | National Institute Of Advanced Industrial Science & Technology | ポリエステル樹脂の製造方法 |
Also Published As
Publication number | Publication date |
---|---|
US20140371419A1 (en) | 2014-12-18 |
CA2852325A1 (en) | 2014-12-18 |
CA2852325C (en) | 2018-08-28 |
DE102014210818A1 (de) | 2014-12-18 |
CN104231243A (zh) | 2014-12-24 |
CN104231243B (zh) | 2018-10-12 |
KR20140147013A (ko) | 2014-12-29 |
US10184024B2 (en) | 2019-01-22 |
RU2664931C2 (ru) | 2018-08-23 |
RU2014124524A (ru) | 2015-12-27 |
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