JP2022549530A - ジオキサジン顔料組成物、ジオキサジン顔料組成物の製造方法 - Google Patents
ジオキサジン顔料組成物、ジオキサジン顔料組成物の製造方法 Download PDFInfo
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- JP2022549530A JP2022549530A JP2022536592A JP2022536592A JP2022549530A JP 2022549530 A JP2022549530 A JP 2022549530A JP 2022536592 A JP2022536592 A JP 2022536592A JP 2022536592 A JP2022536592 A JP 2022536592A JP 2022549530 A JP2022549530 A JP 2022549530A
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- formula
- dioxazine pigment
- pigment composition
- dioxazine
- hydrogen atom
- Prior art date
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- 239000000049 pigment Substances 0.000 title claims abstract description 146
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- 239000000203 mixture Substances 0.000 title claims abstract description 64
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 22
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- 125000005843 halogen group Chemical group 0.000 claims description 13
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- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical group CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 claims description 12
- 238000007363 ring formation reaction Methods 0.000 claims description 11
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- TUXHHVJPGQUPCF-UHFFFAOYSA-N Spiculisporic acid Natural products CCCCCCCCCCC(C(O)=O)C1(C(O)=O)CCC(=O)O1 TUXHHVJPGQUPCF-UHFFFAOYSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- QYTDEUPAUMOIOP-UHFFFAOYSA-N TEMPO Chemical group CC1(C)CCCC(C)(C)N1[O] QYTDEUPAUMOIOP-UHFFFAOYSA-N 0.000 description 1
- 229910007926 ZrCl Inorganic materials 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000005456 alcohol based solvent Substances 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 239000002635 aromatic organic solvent Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 239000003876 biosurfactant Substances 0.000 description 1
- QAJHFVRPDSGYSZ-UHFFFAOYSA-N butyl 2-phenylbenzenesulfonate Chemical compound CCCCOS(=O)(=O)C1=CC=CC=C1C1=CC=CC=C1 QAJHFVRPDSGYSZ-UHFFFAOYSA-N 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 description 1
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- URSLCTBXQMKCFE-UHFFFAOYSA-N dihydrogenborate Chemical compound OB(O)[O-] URSLCTBXQMKCFE-UHFFFAOYSA-N 0.000 description 1
- 150000005125 dioxazines Chemical class 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- YRIUSKIDOIARQF-UHFFFAOYSA-N dodecyl benzenesulfonate Chemical compound CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 YRIUSKIDOIARQF-UHFFFAOYSA-N 0.000 description 1
- 229940071161 dodecylbenzenesulfonate Drugs 0.000 description 1
- 239000003759 ester based solvent Substances 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 229910052758 niobium Inorganic materials 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229920002114 octoxynol-9 Polymers 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- ARENMZZMCSLORU-UHFFFAOYSA-N propan-2-yl naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)OC(C)C)=CC=CC2=C1 ARENMZZMCSLORU-UHFFFAOYSA-N 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 239000001057 purple pigment Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 229910052713 technetium Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/22—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains four 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
- C09B19/00—Oxazine dyes
- C09B19/02—Bisoxazines prepared from aminoquinones
-
- 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
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pigments, Carbon Blacks, Or Wood Stains (AREA)
Abstract
Description
項1. 下記式(I)で表されるジオキサジン顔料
と、下記式(II)で表される顔料誘導体
と、を含むジオキサジン顔料組成物。
項2. 式(I)で表されるジオキサジン顔料100質量部に対して、式(II)で表される顔料誘導体を0.3~10.0質量部含む項1に記載のジオキサジン顔料組成物。
項3. 項1または2に記載のジオキサジン顔料組成物を含有する印刷インキ。
項4. 下記式(III)で表される化合物
を、下記式(IV)で表される化合物
と、2~4価の金属塩の存在下、溶剤中で環化反応をすることにより、
下記式(I)で表されるジオキサジン顔料
と、下記式(II)で表される顔料誘導体
と、を含むジオキサジン顔料組成物を得る、ジオキサジン顔料組成物の製造方法。
項5. 式(III)で表される化合物1モルに対して、式(IV)で表される化合物を0.01~0.3モル、且つ2~4価の金属塩を0.05~1.0モル使用する項4に記載のジオキサジン顔料組成物の製造方法。
項6. 前記溶剤がメチル安息香酸、1,2-ジクロロベンゼン、N-メチルピロリドン、3-メトキシブタノール、又はジメチルスルホキシドである項4又は5に記載のジオキサジン顔料組成物の製造方法。
項7. 式(I)で表されるジオキサジン顔料100質量部に対して、式(II)で表される顔料誘導体を0.3~10.0質量部含む項4~6のいずれか1項に記載のジオキサジン顔料組成物の製造方法。
本発明のジオキサジン顔料組成物は、式(I)で表されるジオキサジン顔料と式(II)で表される顔料誘導体とを含む。
本発明のジオキサジン顔料組成物の製造方法は、下記式(III)で表される化合物を、下記式(IV)で表される化合物と、2~4価の金属塩の存在下、溶剤中で環化反応をすることにより、上記式(I)で表されるジオキサジン顔料と上記式(II)で表される顔料誘導体、つまりは上記の本発明のジオキサジン顔料組成物を得る方法である。
本発明のジオキサジン顔料組成物は、分散性および分散安定性に優れるため印刷インキとして特に有用である。本発明の印刷インキは、上記本発明のジオキサジン顔料組成物を含む限り特に制限はないが、一般的に印刷インキに用いることができる公知慣用のバインダー樹脂、溶媒、添加剤等を含むことが好ましい。本発明の印刷インキにおける上記ジオキサジン顔料組成物の量は2~60質量%であることが好ましく、4~25質量%がより好ましい。
1000mLの4ツ口フラスコに、42gの3-アミノ-N-エチルカルバゾールと、300mLの1,2-ジクロロベンゼンを入れ、撹拌して溶解させる。次いで、温度を36℃に上げ、200mLの1,2-ジクロロベンゼンに混合溶解させた28gのクロラニルと21gのトリエチルアミンを加え、36℃で4時間撹拌する。反応終了後、反応液を濾過し、濾物を200mLの1,2-ジクロロベンゼンと5Lの60℃温水で洗浄した。得られた濾物を100℃の送風乾燥機で17時間乾燥させ、中間体1を70.6g得た。
まず、上記製造例1で得た中間体1 5.9gをメチル安息香酸150mlに投入し、80℃で20分間攪拌した。次に、TEMPO(関東化学株式会社製試薬)0.15gと塩化亜鉛(関東化学株式会社製試薬)0.5gを加え、160℃で16時間攪拌した。100℃まで冷却後、生じた固体を濾過し、メチル安息香酸30g、N-メチル-2-ピロリドン30gと水30gで洗浄した。得られたケーキを加熱乾燥してジオキサジン顔料組成物1(3.1g、収率53%)を得た。ジオキサジン顔料組成物1について、FD-MS測定(質量分析)を行ったところ、m/z536と570のピークが検出された。よって、ジオキサジン顔料組成物1は、C.I.ピグメントバイオレット23とともに、以下の顔料誘導体1(ノミナル質量:570)と顔料誘導体2(ノミナル質量:536)を含むことが分かった。
まず、上記製造例1で得た中間体1 5.9gを1,2-ジクロロベンゼン150mlに投入し、80℃で20分間攪拌した。次に、TEMPO(関東化学株式会社製試薬)0.15gと塩化亜鉛(関東化学株式会社製試薬)0.5gを加え、160℃で16時間攪拌した。100℃まで冷却後、生じた固体を濾過し、メチル安息香酸30g、N-メチル-2-ピロリドン30gと水30gで洗浄した。得られたケーキを加熱乾燥してジオキサジン顔料組成物2(2.7g、収率46%)を得た。ジオキサジン顔料組成物1について、FD-MS測定(質量分析)を行ったところ、m/z536と570のピークが検出された。よって、ジオキサジン顔料組成物2は、実施例1と同様にC.I.ピグメントバイオレット23とともに、顔料誘導体1(ノミナル質量:570)と顔料誘導体2(ノミナル質量:536)を含むことが分かった。
特開2004-189668号公報の段落番号[0067]を参考にしてC.I.ピグメントバイオレット23を合成した。このジオキサジン顔料について、FD-MS測定(質量分析)を行ったところ、m/z536と570のピークは検出されなかった。よって、比較例1の合成方法では、顔料誘導体は含まれていないことが分かった。また、m/z628、634、662のピークが検出された。これらの分子量のピークは下記の硫黄元素を含む不純物であると推測される。このように比較例1の合成方法では、硫黄元素を含む不純物を含有することが分かった。
実施例1及び2で得られたジオキサジン顔料組成物、比較例1で得られたジオキサジン顔料について分散性と分散安定性の評価を行った。顔料組成物又は顔料の粉末約10mgを分散媒として水5ml加えた10mLガラス瓶に入れ、分散させるために超音波をかけた。
分散性は超音波をかけた直後(0h)、分散安定性は18h後と72h後で評価を行った。評価基準は以下のとおりである。
<評価基準>
1:無色透明の液体と紫色固体の沈殿物に分離した。
2:薄い紫色の液体中に紫色固体の沈殿物が生じた。
3:紫色の液体中に紫色固体の沈殿物が生じた。
4:濃い紫色の液体中に紫色固体の沈殿物が生じた。
5:ジオキサジン顔料は完全に分散した状態で、紫色固体の沈殿物は見られない。
Claims (7)
- 式(I)で表されるジオキサジン顔料100質量部に対して、式(II)で表される顔料誘導体を0.3~10.0質量部含む請求項1に記載のジオキサジン顔料組成物。
- 請求項1または2に記載のジオキサジン顔料組成物を含有する印刷インキ。
- 下記式(III)で表される化合物
を、下記式(IV)で表される化合物
と、2~4価の金属塩の存在下、溶剤中で環化反応をすることにより、
下記式(I)で表されるジオキサジン顔料
と、下記式(II)で表される顔料誘導体
と、を含むジオキサジン顔料組成物を得る、ジオキサジン顔料組成物の製造方法。 - 式(III)で表される化合物1モルに対して、式(IV)で表される化合物を0.01~0.3モル、且つ2~4価の金属塩を0.05~1.0モル使用する請求項4に記載のジオキサジン顔料組成物の製造方法。
- 前記溶剤がメチル安息香酸、1,2-ジクロロベンゼン、N-メチルピロリドン、3-メトキシブタノール、又はジメチルスルホキシドである請求項4又は5に記載のジオキサジン顔料組成物の製造方法。
- 式(I)で表されるジオキサジン顔料100質量部に対して、式(II)で表される顔料誘導体を0.3~10.0質量部含む請求項4~6のいずれか1項に記載のジオキサジン顔料組成物の製造方法。
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JPS62185088A (ja) * | 1986-02-12 | 1987-08-13 | Nippon Kayaku Co Ltd | カルバゾ−ルジオキサジン化合物及びその用途 |
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DE19913401A1 (de) * | 1999-03-25 | 2000-09-28 | Clariant Gmbh | Verfahren zur Herstellung von Dioxazin-Verbindungen |
TW201105750A (en) * | 2009-03-31 | 2011-02-16 | Solvay | Process for the preparation of easily dispersible violet pigment |
IN2013MU01531A (ja) * | 2013-04-26 | 2015-04-17 | Keki Hormusji Gharda | |
WO2015136814A1 (ja) * | 2014-03-10 | 2015-09-17 | Dic株式会社 | 遮光性顔料組成物及びディスプレイ用遮光性部材 |
CN104031400B (zh) * | 2014-06-25 | 2016-04-27 | 南通海迪化工有限公司 | 一种永固紫颜料的制备方法 |
CN111100473B (zh) * | 2019-12-11 | 2021-03-09 | 浙江浩川科技有限公司 | 一种颜料紫23粗品的制备方法 |
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JPH0848687A (ja) * | 1994-05-30 | 1996-02-20 | Nippon Kayaku Co Ltd | ジオキサジン化合物の製造方法、着色材料及び板状結晶 |
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WO2012001708A1 (en) * | 2010-06-30 | 2012-01-05 | Gharda Keki Hormusji | Process for preparing of dioxazine pigments |
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