JP4604478B2 - 新規色素、着色組成物、インクジェット記録液、及びインクジェット記録方法 - Google Patents
新規色素、着色組成物、インクジェット記録液、及びインクジェット記録方法 Download PDFInfo
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- JP4604478B2 JP4604478B2 JP2003388916A JP2003388916A JP4604478B2 JP 4604478 B2 JP4604478 B2 JP 4604478B2 JP 2003388916 A JP2003388916 A JP 2003388916A JP 2003388916 A JP2003388916 A JP 2003388916A JP 4604478 B2 JP4604478 B2 JP 4604478B2
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- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- 229910001927 ruthenium tetroxide Inorganic materials 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000010420 shell particle Substances 0.000 description 1
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 1
- 229940056910 silver sulfide Drugs 0.000 description 1
- XUARKZBEFFVFRG-UHFFFAOYSA-N silver sulfide Chemical compound [S-2].[Ag+].[Ag+] XUARKZBEFFVFRG-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 125000004436 sodium atom Chemical group 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 230000002123 temporal effect Effects 0.000 description 1
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- PMBKSTOGTODXJZ-UHFFFAOYSA-N tetracosane-1,1-diol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCC(O)O PMBKSTOGTODXJZ-UHFFFAOYSA-N 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000004149 thio group Chemical group *S* 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- 229950006389 thiodiglycol Drugs 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- UIERETOOQGIECD-ONEGZZNKSA-N tiglic acid Chemical compound C\C=C(/C)C(O)=O UIERETOOQGIECD-ONEGZZNKSA-N 0.000 description 1
- UAXOELSVPTZZQG-UHFFFAOYSA-N tiglic acid Natural products CC(C)=C(C)C(O)=O UAXOELSVPTZZQG-UHFFFAOYSA-N 0.000 description 1
- LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- ZTWTYVWXUKTLCP-UHFFFAOYSA-N vinylphosphonic acid Chemical compound OP(O)(=O)C=C ZTWTYVWXUKTLCP-UHFFFAOYSA-N 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 125000001834 xanthenyl group Chemical class C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 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
- C09D11/32—Inkjet printing inks characterised by colouring agents
- C09D11/328—Inkjet printing inks characterised by colouring agents characterised by dyes
-
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- 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
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/02—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic ring being only condensed in peri position
- C09B5/14—Benz-azabenzanthrones (anthrapyridones)
-
- 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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/006—Preparation of organic pigments
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Ink Jet Recording Methods And Recording Media Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Ink Jet (AREA)
Description
(請求項1)
下記一般式(2)または(3)で表されることを特徴とする色素。
(請求項2)
請求項1に記載の色素の少なくとも1種を含有することを特徴とする着色組成物。
(請求項3)
請求項1に記載の色素の少なくとも1種を含有することを特徴とするインクジェット記録液。
(請求項4)
前記色素が、スルホ基または、その塩を有することを特徴とする請求項3記載のインクジェット記録液。
(請求項5)
前記色素が、微粒子分散物として含有されることを特徴とする請求項3に記載のインクジェット記録液。
(請求項6)
前記微粒子分散物が油溶性ポリマーを含むことを特徴とする請求項5記載のインクジェット記録液。
(請求項7)
請求項3〜6のいずれか1項記載のインクジェット記録液を用いて記録を行うことを特徴とするインクジェット記録方法。
水系溶媒としては、水(例えば、イオン交換水が好ましい)と水溶性有機溶媒との混合系が好ましく用いられる。
本発明に係る、前記一般式(1)〜(3)で表される色素の微粒子分散物について説明する。
本発明に係る微粒子分散物を構成する微粒子がコア/シェル構造を形成する場合、コア部とシェル部の構成としては下記のような組み合わせがある。
(1) 色素 樹脂
(2) 色素+樹脂 樹脂
上記の組み合わせの中でも、コア/シェル粒子の分散安定性向上の観点から、コア部が樹脂や色素を含み、シェル部が樹脂により構成されている組み合わせ(2)が好ましい。
コアシェル構造の安定性向上(コアの一部が粒子表面に現れるのを防止し、また、コア部の色素保護性を向上させる)の観点から、シェルに用いられる樹脂量が総樹脂量の5質量%〜95質量%の範囲であることが好ましく、更に好ましくは、10質量%〜90質量%である。
インク吐出後の画像濃度を適性に保ちながら、且つ、色素に対する樹脂の保護能を十分に機能させる観点から、色素の質量は総樹脂量に対して20質量%〜1000質量%の範囲であることが好ましい。
本発明において、前記一般式(1)〜(3)で表される色素が水系溶媒系に不溶であり、微粒子状に分散させる場合、前記微粒子分散物中の微粒子(着色微粒子)の粒径としては、平均粒径が150nm以下になるように分散されていることがさらに好ましい。
ここで、微粒子の体積平均粒子径は、透過型電子顕微鏡(TEM)写真の投影面積(少なくとも100粒子以上に対して求める)の平均値から得られた円換算平均粒径を、球形換算して求められる。体積平均粒子径とその標準偏差を求め、標準偏差を体積平均粒子径で割ることで変動係数を求められる。或いは、動的光散乱法を利用して変動係数を求めることも出来る。例えば、大塚電子製レーザ粒径解析システムや、マルバーン社製ゼータサイザを用いて求めることが出来る。
粒子径の変動係数は、粒子径の標準偏差を粒子径で割った値であるが、この値が大きいほど粒子径の分布が広いことを意味する。
本発明に係るコア/シェル構造を有する微粒子は、最初に、本発明に係る色素を含有する樹脂コアを作製した後、樹脂シェルを設ける方法と、コア及びシェルを同時に設ける手法等が挙げられる。
コアとなる色素含有(色素を含むともいう)樹脂は、各種の手法で調製することができる。例えば、色素と樹脂とを混練し、その後、水系で分散し樹脂被覆色素を作製する手法などがある。それに樹脂シェルを設ける手法としては、コアとなる樹脂の水系サスペンションに水溶性の樹脂分散剤を添加し吸着させる手法、モノマーを徐々に滴下し、重合と同時にコア表面に沈着させる方法、あるいは、有機溶剤に溶解した樹脂を徐々に滴下し、析出と同時にコア表面に吸着させる方法などがある。
コアとなる樹脂と色材(色素)を、重合後にシェルとなるモノマーに溶解または分散し、水中で懸濁後重合する手法や、その液を活性剤ミセルを含有する水中に徐々に滴下しながら乳化重合していく手法などもある。モノマーがコア、樹脂がシェルとなってもよい。あるいは、重合後にコアとなりうるモノマーとシェルとなりうるモノマー混合液に色素を溶解または分散し、懸濁重合あるいは乳化重合する手法もある。
着色微粒子が実際にコアシェル化されているかを評価することは重要である。本発明では後述するように、着色微粒子の個々の粒子径が200nm以下と非常に微小であるため、分析手法は分解能の観点から限られたものとなる。
着色微粒子分散物の形成用樹脂に求められる物性とは、前記一般式(1)〜(3)のいずれか1種の色素との相溶性、親和性が高いことは勿論のこと、色調、保存性を良くするための相互作用が強いこと、分散系を保つために適度な疎水性を有し、且つ、分散安定性を向上するための適度な親水性を同時に有し、更に、耐光性を上げるためにはガラス転移点(Tg)が高いことなど(但し分散安定性を上げるためには低Tgである方がよい)多様な性質が要求される。
本発明のインクジェット記録液は、微粒子分散物(着色粒子分散物)の水系媒体を用いるインク中での経時安定性を向上させる観点から、前記微粒子分散物が、前記色素と油溶性ポリマー(親油性ポリマー)とを含む態様が好ましい。
(d)本発明に係る微粒子分散物が、コア領域(樹脂と色素とを含む)と前記コア領域を被覆するように形成されたシェル領域(樹脂を含む)からなるコアシェル粒子の分散物として調製される場合
前記(c)の態様の好ましい一例としては、前記一般式(1)〜(3)で表される色素を、可溶である有機溶媒(親油性溶媒ともいう)に溶解した後、油溶性ポリマー(親油性ポリマーともいう)と共に、微粒子分散物を調製し、水系溶媒に分散させる等が挙げられる。
水分散型のポリマーとしては、イオン解離型のもの、非イオン性分散性基含有型のもの、あるいはこれらの混合型のもののいずれでもよい。前記イオン解離型のポリマーとしては、三級アミノ基などのカチオン性の解離性基を含有するポリマーや、カルボン酸、スルホン酸などのアニオン性の解離性基を含有するポリマーが挙げられる。前記非イオン性分散性基含有型のポリマーとしては、ポリエチレンオキシ鎖などの非イオン性分散性基を含有するポリマーが挙げられる。
メタクリル酸エステル類、具体的には、メチルメタクリレート、エチルメタクリレート、n−プロピルメタクリレート、イソプロピルメタクリレート、n−ブチルメタクリレート、イソブチルメタクリレート、sec−ブチルメタクリレート、tert−ブチルメタクリレート、アミルメタクリレート、ヘキシルメタクリレート、シクロヘキシルメタクリレート、ベンジルメタクリレート、クロロベンジルメタクリレート、オクチルメタクリレート、ステアリルメタクリレート、2−(3−フェニルプロピルオキシ)エチルメタクリレート、フルフリルメタクリレート、テトラヒドロフルフリルメタクリレート、フェニルメタクリレート、クレジルメタクリレート、ナフチルメタクリレート、2−ヒドロキシエチルメタクリレート、4−ヒドロキシブチルメタクリレート、トリエチレングリコールモノメタクリレート、ジプロピレングリコールモノメタクリレート、2−メトキシエチルメタクリレート、3−メトキシブチルメタクリレート、2−エトキシエチルメタクリレート、2−iso−プロポキシエチルメタクリレート、2−ブトキシエチルメタクリレート、2−(2−メトキシエトキシ)エチルメタクリレート、2−(2−エトキシエトキシ)エチルメタクリレート、2−(2−ブトキシエトキシ)エチルメタクリレート、2−アセトキシエチルメタクリレート、2−アセトアセトキシエチルメタクリレート、アリルメタクリレート、グリシジルメタクリレート、2,2,2−テトラフルオロエチルメタクリレート、1H,1H,2H,2H−パーフルオロデシルメタクリレート等;
ビニルエステル類、具体的には、ビニルアセテート、ビニルプロピオネート、ビニルブチレート、ビニルイソブチレート、ビニルカプロエート、ビニルクロロアセテート、ビニルメトキシアセテート、ビニルフェニルアセテート、安息香酸ビニル、サリチル酸ビニル等;
アクリルアミド類、具体的には、アクリルアミド、メチルアクリルアミド、エチルアクリルアミド、プロピルアクリルアミド、ブチルアクリルアミド、tert−ブチルアクリルアミド、tert−オクチルアクリルアミド、シクロヘキシルアクリルアミド、ベンジルアクリルアミド、ヒドロキシメチルアクリルアミド、メトキシメチルアクリルアミド、ブトキシメチルアクリルアミド、メトキシエチルアクリルアミド、フェニルアクリルアミド、ジメチルアクリルアミド、ジエチルアクリルアミド、β−シアノエチルアクリルアミド、N−(2−アセトアセトキシエチル)アクリルアミド、ジアセトンアクリルアミド等;
メタクリルアミド類、具体的には、メタクリルアミド、メチルメタクリルアミド、エチルメタクリルアミド、プロピルメタクリルアミド、ブチルメタクリルアミド、tert−ブチルメタクリルアミド、シクロヘキシルメタクリルアミド、ベンジルメタクリルアミド、ヒドロキシメチルメタクリルアミド、メトキシエチルメタクリルアミド、フェニルメタクリルアミド、ジメチルメタクリルアミド、β−シアノエチルメタクリルアミド、N−(2−アセトアセトキシエチル)メタクリルアミド等;
オレフィン類、具体的には、ジシクロペンタジエン、エチレン、プロピレン、1−ブテン、1−ペンテン、塩化ビニル、塩化ビニリデン、イソプレン、クロロプレン、ブタジエン、2,3−ジメチルブタジエン等、スチレン類、例えば、スチレン、メチルスチレン、ジメチルスチレン、トリメチルスチレン、エチルスチレン、イソプロピルスチレン、クロルメチルスチレン、メトキシスチレン、アセトキシスチレン、クロルスチレン、ジクロルスチレン、ブロムスチレン、ビニル安息香酸メチルエステル等;
ビニルエーテル類、具体的には、メチルビニルエーテル、ブチルビニルエーテル、ヘキシルビニルエーテル、メトキシエチルビニルエーテル等;
その他のモノマーとして、クロトン酸ブチル、クロトン酸ヘキシル、イタコン酸ジメチル、イタコン酸ジブチル、マレイン酸ジエチル、マレイン酸ジメチル、マレイン酸ジブチル、フマル酸ジエチル、フマル酸ジメチル、フマル酸ジブチル、メチルビニルケトン、フェニルビニルケトン、メトキシエチルビニルケトン、N−ビニルオキサゾリドン、N−ビニルピロリドン、ビニリデンクロライド、メチレンマロンニトリル、ビニリデン、ジフェニル−2−アクリロイルオキシエチルホスフェート、ジフェニル−2−メタクリロイルオキシエチルホスフェート、ジブチル−2−アクリロイルオキシエチルホスフェート、ジオクチル−2−メタクリロイルオキシエチルホスフェート等;が挙げられる。
また、本発明では樹脂として、従来公知のポリマー(樹脂)が使用可能であるが、好ましいポリマーとしては、主な官能基としてアセタール基を含有するポリマー、炭酸エステル基を含有するポリマー、水酸基を含有するポリマーおよびエステル基を有するポリマーなどであり、特にアセタール基を含有するポリマー、中でもポリビニルブチラール等が挙げられる。
本発明において用いられるこれらの樹脂(ポリマー)としてはその数平均分子量が500〜100,000、特に1,000〜30,000であることが、印刷後の製膜性、その耐久性及びサスペンションの形成性の点から好ましい。
樹脂のガラス転移点(Tg)としては、各種用いることが可能であるが、用いるポリマーのうち、少なくとも1種以上はTgが10℃以上であるものを用いる方が好ましい。
本発明に係る微粒子分散物の調製に用いられる有機溶媒(親油性溶媒)について説明する。
本発明に使用される固体(相変化)溶媒は、溶媒として室温で固体であり、且つ、インクジェット記録液の加熱噴射時には溶融した液体状である相変化溶媒を使用する。
本発明に用いられるインクジェット記録方法について説明する。
(例示化合物1−1の合成)
なお、上記実施例1で使用した化合物Bは以下のようにして合成した。
なお、上記実施例2で使用した化合物Dは以下のようにして合成した。
《インクジェット記録液1〜6の作製:水系インク》
表1に記載の化合物の仕上がりインク中の含有量が、2質量%になるように秤量し、これに、エチレングリコール15質量%、グリセリン15質量%、サーフィノール465(日信化学工業社製)0.3質量%、残りが純水になるように調整して純水を加え、混合分散し、2μmのメンブランフィルターによって濾過し、ゴミ及び粗大粒子を除去して、表1に示すようなインクジェット記録液1〜6を得た。用いた比較化合物の構造式を下記に示す。
上記で得たインクジェット記録液1〜6の各々のインクを市販のエプソン製インクジェットプリンター(PM−800)を用いてコニカフォトジェットペーパー Photolike QP 光沢紙(コニカミノルタフォトイメージング株式会社製)にプリントし、得られた画像試料1〜6について、下記のように画像の耐光性、画像の色調およびインクの保存性の評価を行った。
得られた試料にキセノンフェードメーターで48時間光照射を行い、各画像の色素残存率で耐光性を評価した。尚、色素残存率(%)は、光照射前の濃度をD0、光照射後の濃度をDとして、
耐光性(%)=D/D0×100(%)
で表す。尚、濃度はコニカミノルタフォトイメージング株式会社製PDA−65濃度計を用い測定した。
画像試料の390nm〜730nm領域のインターバル10nmによる反射スペクトルを測定し、これをCIE L*a*b*色空間系に基づいて、a*、b*を算出した。
△:a*、b*の一方のみ好ましい領域
×:a*、b*のいずれも好ましい領域外
《インクの保存性評価》
インクジェット記録液1〜6を80℃で1週間、密閉ガラス容器中に保存後、上記画像試料の作製の場合と同様にして画像を作製し、500時間の連続吐出における吐出異常の有無を観察した。また該画像について色調の評価を上記と同様にして行って、保存性を下記の評価基準により評価した。
×:連続吐出に異常が認められる、未保存インクからの色調変化がa*またはb*の少なくとも一方に、絶対値で10以上認められる
得られた結果を表1に示す。
《微粒子分散物の調製》
表2に記載の化合物を10g、メチルエチルケトン20g、グリセリン5g、共重合ポリマー(スチレン/アクリル酸/2−ヒドロキシエチルメタクリレート=80/5/15の共重合比である、中和済み樹脂)を6g、イオン交換水40gの混合液に、平均粒子径が0.5mmのジルコニアビーズ250gを加え、メディア分散機(システムゼータ;(株)アシザワ製)を用いて4時間分散を行った。分散終了後、ジルコニアビーズを濾別して分散液を得た。この分散液に水40mlを加えて希釈した後、減圧留去によりメチルエチルケトンを除去し微粒子分散物を得た。
表2に記載の化合物の含有量がインクジェット記録液の仕上がり量に対して3質量%になるように、上記微粒子分散物を秤量し、エチレングリコール15質量%、グリセリン15質量%、トリエチレングリコールモノブチルエーテル3質量%、サーフィノール465を0.3質量%、残りが純水になるように調整し、混合分散し、次いで、2μmのメンブランフィルターによって濾過し、ゴミ及び粗大粒子を除去して表2に示すようにインクジェット記録液7〜12を得た。
インクジェット記録液7〜12について、60℃で7日間保存した際の平均粒子径変化率、保存後のインクの濾過性を下記のように評価した。
インクジェット記録液7〜12を、各々60℃で7日間保管し、大塚電子製レーザ粒径解析システムを用いて保存後のインクの平均(体積平均)粒子径を求め、同様にして求めた未保存の場合のインクの平均粒子径との平均粒子径変化率を下式にて求め、下記基準によりランク評価した。
×:10%以上(実用不可レベル)
○:5%〜10%未満(実用許容レベル)
◎:粒子径変化率が5%未満
(インクの濾過性評価)
インクジェット記録液7〜12を60℃で7日間保管した後に、5ml採取し、0.8μmのセルロースアセテートメンブランフィルターで濾過を行い、下記のようにランク評価した。
○:半量以上濾過できたもの(実用可)
×:半量未満しか濾過ができなかったもの(不可レベル)
本発明では、◎、○が実用可のレベルである。
インクジェット記録液7〜12の各々のインクを用いて実施例3と同様に画像試料7〜12を作製し、画像の色調を評価した。
《微粒子分散物の作製》:コアシェル構造粒子
表3に示す化合物を5g、5gのポリビニルブチラール(積水化学製BL−S、平均重合度350)及び50gの酢酸エチルをセパラブルフラスコに入れ、フラスコ内をN2ガスで置換後、攪拌して上記ポリビニルブチラール及び化合物を完全溶解させた。
色素の含有量がインクの仕上がり量に対して2質量%になる量の上記着色微粒子分散物を秤量し、これに、エチレングリコール15質量%、グリセリン15質量%、トリエチレングリコールモノブチルエーテル3質量%、サーフィノール465を0.3質量%、残りが純水になるように調整して純水を加え混合分散し、更に2μmのメンブランフィルターによって濾過し、ゴミ及び粗大粒子を除去して表3に示すようにインクジェット記録液14〜18を得た。
インクジェット記録液14〜18について、60℃で7日間保存した際の平均粒子径変化率、保存後のインクの濾過性を実施例4と同様に評価した。
インクジェット記録液14〜18の各々のインクを用いて実施例3と同様に画像試料14〜18を作製し、画像の色調、画像の耐光性を評価した。
Claims (7)
- 請求項1に記載の色素の少なくとも1種を含有することを特徴とする着色組成物。
- 請求項1に記載の色素の少なくとも1種を含有することを特徴とするインクジェット記録液。
- 前記色素が、スルホ基または、その塩を有することを特徴とする請求項3記載のインクジェット記録液。
- 前記色素が、微粒子分散物として含有されることを特徴とする請求項3に記載のインクジェット記録液。
- 前記微粒子分散物が油溶性ポリマーを含むことを特徴とする請求項5記載のインクジェット記録液。
- 請求項3〜6のいずれか1項記載のインクジェット記録液を用いて記録を行うことを特徴とするインクジェット記録方法。
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JP2003388916A JP4604478B2 (ja) | 2003-11-19 | 2003-11-19 | 新規色素、着色組成物、インクジェット記録液、及びインクジェット記録方法 |
US10/986,981 US7025816B2 (en) | 2003-11-19 | 2004-11-12 | Anthraquinone dye and inkjet recording liquid |
GB0425045A GB2408266B (en) | 2003-11-19 | 2004-11-12 | Anthraquinone dye and inkjet recording liquid |
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US7785410B2 (en) * | 2006-06-30 | 2010-08-31 | Videojet Technologies Inc. | Ink jet ink composition and method for printing on substrates under conditions of high static electrical charge |
US7947124B2 (en) * | 2006-06-30 | 2011-05-24 | Videojet Technologies Inc. | High electrical resistivity ink jet ink composition |
US7740694B2 (en) * | 2006-06-30 | 2010-06-22 | Videojet Technologies Inc | Ink jet ink composition and method for printing |
US7520926B2 (en) * | 2006-09-15 | 2009-04-21 | Videojet Technologies Inc. | Solvent-based ink composition |
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JP2000256587A (ja) * | 1999-03-04 | 2000-09-19 | Nippon Kayaku Co Ltd | 水性インクセット、着色方法及びその着色体 |
JP2002332418A (ja) * | 2001-05-09 | 2002-11-22 | Nippon Kayaku Co Ltd | アントラピリドン化合物、水性マゼンタインク組成物及びインクジェット記録方法 |
JP2005126587A (ja) * | 2003-10-24 | 2005-05-19 | Konica Minolta Holdings Inc | 色素、着色微粒子分散物、インクジェット用インク及びインクジェット記録方法 |
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US2187812A (en) * | 1936-05-26 | 1940-01-23 | Gen Aniline Works Inc | Vat dyestuff of the quinazoline series |
US3839332A (en) * | 1967-08-18 | 1974-10-01 | Ciba Geigy Ag | Process for the manufacture of anthraquinone dyestuffs |
JPS5974173A (ja) * | 1982-10-22 | 1984-04-26 | Nippon Kayaku Co Ltd | 赤色水性インク |
JPH0216171A (ja) * | 1988-07-05 | 1990-01-19 | Ricoh Co Ltd | 水性インク |
WO1997032059A1 (fr) * | 1996-02-29 | 1997-09-04 | Sumitomo Sitix Corporation | Procede et appareil pour retirer un monocristal |
EP0927747B1 (en) * | 1996-09-11 | 2006-07-19 | Nippon Kayaku Kabushiki Kaisha | Anthrapyridone compounds, water-base ink composition, and articles colored therewith |
TWI235156B (en) * | 1998-10-22 | 2005-07-01 | Nippon Kayaku Kk | Novel anthrapyridone compound, aqueous magenta ink composition and ink-jet recording method |
US6843839B2 (en) * | 2000-06-12 | 2005-01-18 | Canon Kabushiki Kaisha | Ink, recording method, recording unit, ink cartridge, ink set, and recording apparatus |
US20030070580A1 (en) * | 2001-08-01 | 2003-04-17 | Eastman Kodak Company | Ink jet ink set |
DE60212423T2 (de) * | 2001-09-26 | 2006-10-19 | Nippon Kayaku K.K. | Neue anthrapyridonverbindungen, wässrige magentatinten und tintenstrahlaufzeichnungsverfahren |
JP4300752B2 (ja) * | 2002-05-22 | 2009-07-22 | コニカミノルタホールディングス株式会社 | インクジェット記録液 |
JP3979186B2 (ja) * | 2002-05-28 | 2007-09-19 | コニカミノルタホールディングス株式会社 | インクジェット記録液 |
JP2004190007A (ja) * | 2002-11-27 | 2004-07-08 | Konica Minolta Holdings Inc | 色素およびインクジェット記録液 |
JP4374917B2 (ja) * | 2003-06-12 | 2009-12-02 | コニカミノルタホールディングス株式会社 | インクジェット記録液 |
JP4186775B2 (ja) * | 2003-09-30 | 2008-11-26 | セイコーエプソン株式会社 | インクセット |
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JP2000256587A (ja) * | 1999-03-04 | 2000-09-19 | Nippon Kayaku Co Ltd | 水性インクセット、着色方法及びその着色体 |
JP2002332418A (ja) * | 2001-05-09 | 2002-11-22 | Nippon Kayaku Co Ltd | アントラピリドン化合物、水性マゼンタインク組成物及びインクジェット記録方法 |
JP2005126587A (ja) * | 2003-10-24 | 2005-05-19 | Konica Minolta Holdings Inc | 色素、着色微粒子分散物、インクジェット用インク及びインクジェット記録方法 |
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US7025816B2 (en) | 2006-04-11 |
US20050103226A1 (en) | 2005-05-19 |
GB2408266A (en) | 2005-05-25 |
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