JP6923168B2 - 不溶性顔料化合物の定性分析方法 - Google Patents
不溶性顔料化合物の定性分析方法 Download PDFInfo
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- 239000000049 pigment Substances 0.000 title claims description 73
- 150000001875 compounds Chemical class 0.000 title claims description 42
- 238000000034 method Methods 0.000 title claims description 19
- 238000004451 qualitative analysis Methods 0.000 title claims description 13
- 238000004458 analytical method Methods 0.000 claims description 16
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 claims description 10
- 239000012634 fragment Substances 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- 238000000527 sonication Methods 0.000 claims description 4
- 230000001678 irradiating effect Effects 0.000 claims description 2
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 claims description 2
- 150000002500 ions Chemical class 0.000 claims 2
- 238000004949 mass spectrometry Methods 0.000 description 46
- 238000005481 NMR spectroscopy Methods 0.000 description 16
- 239000000523 sample Substances 0.000 description 15
- 238000012916 structural analysis Methods 0.000 description 11
- 238000000045 pyrolysis gas chromatography Methods 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 238000000074 matrix-assisted laser desorption--ionisation tandem time-of-flight detection Methods 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 4
- 239000011159 matrix material Substances 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 238000009210 therapy by ultrasound Methods 0.000 description 4
- 238000001097 direct analysis in real time mass spectrometry Methods 0.000 description 3
- 238000013467 fragmentation Methods 0.000 description 3
- 238000006062 fragmentation reaction Methods 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 238000002203 pretreatment Methods 0.000 description 3
- 238000000371 solid-state nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- 238000010561 standard procedure Methods 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 239000000538 analytical sample Substances 0.000 description 2
- 238000012790 confirmation Methods 0.000 description 2
- 238000002149 energy-dispersive X-ray emission spectroscopy Methods 0.000 description 2
- 238000004340 gradient COSY Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000005298 paramagnetic effect Effects 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- 238000000844 transformation Methods 0.000 description 2
- 238000004876 x-ray fluorescence Methods 0.000 description 2
- 206010057175 Mass conditions Diseases 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- VILAVOFMIJHSJA-UHFFFAOYSA-N dicarbon monoxide Chemical compound [C]=C=O VILAVOFMIJHSJA-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 238000000752 ionisation method Methods 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000000816 matrix-assisted laser desorption--ionisation Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- OIASAVWSBWJWBR-UKTHLTGXSA-N trans-2-[3-(4-tert-butylphenyl)-2-methyl-2-propenylidene]malononitrile Chemical compound N#CC(C#N)=CC(/C)=C/C1=CC=C(C(C)(C)C)C=C1 OIASAVWSBWJWBR-UKTHLTGXSA-N 0.000 description 1
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N24/00—Investigating or analyzing materials by the use of nuclear magnetic resonance, electron paramagnetic resonance or other spin effects
- G01N24/08—Investigating or analyzing materials by the use of nuclear magnetic resonance, electron paramagnetic resonance or other spin effects by using nuclear magnetic resonance
- G01N24/087—Structure determination of a chemical compound, e.g. of a biomolecule such as a protein
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N1/00—Sampling; Preparing specimens for investigation
- G01N1/28—Preparing specimens for investigation including physical details of (bio-)chemical methods covered elsewhere, e.g. G01N33/50, C12Q
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N1/00—Sampling; Preparing specimens for investigation
- G01N1/28—Preparing specimens for investigation including physical details of (bio-)chemical methods covered elsewhere, e.g. G01N33/50, C12Q
- G01N1/40—Concentrating samples
- G01N1/4055—Concentrating samples by solubility techniques
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N24/00—Investigating or analyzing materials by the use of nuclear magnetic resonance, electron paramagnetic resonance or other spin effects
- G01N24/08—Investigating or analyzing materials by the use of nuclear magnetic resonance, electron paramagnetic resonance or other spin effects by using nuclear magnetic resonance
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/62—Detectors specially adapted therefor
- G01N30/72—Mass spectrometers
- G01N30/7233—Mass spectrometers interfaced to liquid or supercritical fluid chromatograph
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01J—ELECTRIC DISCHARGE TUBES OR DISCHARGE LAMPS
- H01J49/00—Particle spectrometers or separator tubes
- H01J49/26—Mass spectrometers or separator tubes
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N1/00—Sampling; Preparing specimens for investigation
- G01N1/28—Preparing specimens for investigation including physical details of (bio-)chemical methods covered elsewhere, e.g. G01N33/50, C12Q
- G01N1/40—Concentrating samples
- G01N2001/4038—Concentrating samples electric methods, e.g. electromigration, electrophoresis, ionisation
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N1/00—Sampling; Preparing specimens for investigation
- G01N1/28—Preparing specimens for investigation including physical details of (bio-)chemical methods covered elsewhere, e.g. G01N33/50, C12Q
- G01N1/40—Concentrating samples
- G01N1/4077—Concentrating samples by other techniques involving separation of suspended solids
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Description
2.1.使用機器:LTQ Orbitrap Elite MS及びMALDI−TOF MS
有機溶媒:THF
イオン化法:APCI positive
カラム:Capcellpak C18(4.6mm IDx50mm Lx3μm)
A:ACN/TFA 100/0.1 B:H2O/TFA 100/0.01
−カラム温度:40℃
B582試料1mg及びマトリックス(DCTB)9mgを乳鉢に入れ、磨いてプレートに固体状態でつけて分析サンプルを製造した(Solvent free法)。
Method:RP_12kDa(Reflector、positive)
B582試料を固体状態のそのままMALD−TOF MSで分析した分子量の結果を図1に示した。前記MALD−TOF MS測定結果、分子量448の単一物質が検出され、THFに溶ける成分をLC/MSで分析した結果、分子量319の物質が検出された。前記分子量319の物質は、ブラック顔料試料で分けられた化合物と推定され、分子量448の物質及び分子量319の物質の推定構造は、次の通りである:
[顔料推定構造]
Branson社の5810モデルを使用して、常温で40kHzの超音波を12時間印加した。
Red264[3,6−ジ([1,1'−ビフェニル]−4−イル)−2,5−ジヒドロピロロ[3,4−c]ピロール−1,4−ジオン]であって、主に携帯電話の外装材用顔料として使われ、構造は、次の通りである:
[顔料Red264の代表構造]
Red264試料2mgをMALDIターゲットプレート(target plate)上にヘラ(spatula)でつけて載せた。ターゲットプレート上に載せた前記試料上にN2ガスを流して塊固体を除去した。
3.1.MALDI−TOF/TOF MS分析条件
3.1.1.FlexControl methodとしてLIFT.lftを使用した
Reflectron Positive Mode
Ion Source 1:7.50kV
Ion Source 2:6.75kV
Lens:3.50kV
Reflector:29.50kV
Reflector 2:14.00kV
Pulsed Ion extraction:80ns
LIFT 1:19.00kV
LIFT 2:3.40kV
レーザ強度:レーザ50%(1000Hz)、2500shots
Smartbeam parameter set:3_medium
CID OFF mode
ペアレントマス:m/z 441
前記分析条件で機器を稼動して、機器作動SOP[SOP−0494−0k(Bruker MALDI−TOF/TOF(UltrafleXtreme)の標準作動手続書)とSOP−0496−0k(Bruker MALDI−TOF/TOF(UltrafleXtreme)を活用したMS/MS標準作動手続書)]との手順に従って試料サンプルを分析した。
[レーザフラグメント化された構造]
Py−GC/MSを用いてRed264の構造を分析した。分析結果を下記の表及び図9A及び図9Bに示した。
Claims (5)
- (1)不溶性顔料化合物の分子量を、MSを使用して確認する段階と、
(2)前記不溶性顔料化合物を溶媒に溶解させた後、超音波処理で分解させて得られた部分構造化合物をLC/MS及びNMRで分析する段階と、を含む不溶性顔料化合物の定性分析方法。 - (1)不溶性顔料化合物に対してMALDI−TOF MSでペアレントマスを選別する段階と、
(2)前記ペアレントマスのピークに該当する化合物のイオンに対してのみレーザを照射して、前記化合物をフラグメント化した後、各フラグメントイオンをMSで検出する段階と、を含む不溶性顔料化合物の定性分析方法。 - 前記不溶性顔料化合物が、ビスオキソジヒドロインドリレンベンゾジフラノン系誘導体またはジケトピロロピロール系である請求項1または2に記載の不溶性顔料化合物の定性分析方法。
- 前記溶媒が、THFまたはCHCl3である請求項1または請求項1を引用する請求項3に記載の不溶性顔料化合物の定性分析方法。
- 前記超音波処理は、40kHzの超音波を1〜24時間印加する請求項1、請求項1を引用する請求項3および請求項4のいずれか一項に記載の不溶性顔料化合物の定性分析方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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KR10-2017-0104324 | 2017-08-17 | ||
KR1020170104324A KR102174436B1 (ko) | 2017-08-17 | 2017-08-17 | 불용성 안료 화합물의 정성분석방법 |
PCT/KR2018/001328 WO2019035521A1 (ko) | 2017-08-17 | 2018-01-31 | 불용성 안료 화합물의 정성분석방법 |
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JP2020514744A JP2020514744A (ja) | 2020-05-21 |
JP6923168B2 true JP6923168B2 (ja) | 2021-08-18 |
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US (1) | US11397138B2 (ja) |
EP (1) | EP3671192B1 (ja) |
JP (1) | JP6923168B2 (ja) |
KR (1) | KR102174436B1 (ja) |
WO (1) | WO2019035521A1 (ja) |
Family Cites Families (38)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB8718756D0 (en) * | 1987-08-07 | 1987-09-16 | Unilever Plc | Supporting means |
US7108970B2 (en) * | 2000-01-07 | 2006-09-19 | Transform Pharmaceuticals, Inc. | Rapid identification of conditions, compounds, or compositions that inhibit, prevent, induce, modify, or reverse transitions of physical state |
TW593567B (en) | 2000-07-31 | 2004-06-21 | Ciba Sc Holding Ag | Dispersant compositions improving the heat stability of transparent pigments |
US7973936B2 (en) * | 2001-01-30 | 2011-07-05 | Board Of Trustees Of Michigan State University | Control system and apparatus for use with ultra-fast laser |
JP4455495B2 (ja) * | 2003-05-15 | 2010-04-21 | 株式会社資生堂 | 試料注入方法 |
US20060261267A1 (en) * | 2005-05-20 | 2006-11-23 | Agency For Science, Technology And Research | Composite MALDI matrix material and methods of using it and kits thereof in MALDI |
ES2544238T5 (es) * | 2006-10-11 | 2023-11-08 | Agfa Nv | Métodos para preparar conjuntos de tintas de inyección pigmentadas curables |
WO2009034971A1 (ja) * | 2007-09-12 | 2009-03-19 | Fujifilm Corporation | 置換基脱離化合物の製造方法、有機半導体膜およびその製造方法 |
TW200925216A (en) * | 2007-12-07 | 2009-06-16 | Univ Nat Taiwan | Method for dispersing pigment into solvent |
KR100976097B1 (ko) * | 2008-12-05 | 2010-08-16 | 주식회사 대웅제약 | 이오프로마이드의 z 이성체를 선택적으로 결정화하는 방법 |
MX2011007484A (es) | 2009-01-19 | 2011-08-03 | Basf Se | Dispersion de pigmento negro. |
WO2010138667A1 (en) * | 2009-05-29 | 2010-12-02 | Waters Technologies Corporation | Chromatography apparatus and methods using multiple microfluidic substrates |
JP2011053094A (ja) * | 2009-09-02 | 2011-03-17 | Kao Corp | 分散剤吸着量の測定方法 |
KR101156795B1 (ko) * | 2010-03-10 | 2012-06-18 | 삼성전기주식회사 | 그래핀 코팅된 말디-토프 질량분석용 샘플분석 타겟 및 이를 포함하는 말디-토프 질량분석장치 |
BR112012029811A2 (pt) | 2010-05-24 | 2016-08-09 | Xyleco Inc | processamento de produtos químicos |
WO2012005838A1 (en) * | 2010-07-07 | 2012-01-12 | Thermo Fisher Scientific Gmbh | Analyte mass spectrometry quantitation using a universal reporter |
US20120071615A1 (en) * | 2010-09-14 | 2012-03-22 | Lg Chem, Ltd. | Bi-Nuclear Metallocene Compound and the Preparation Method of Polyolefin Using the Same |
AU2011320345C1 (en) * | 2010-10-29 | 2017-04-06 | Cohesive Technologies Inc. | LC-MS configuration for purification and detection of analytes having a broad range of hydrophobicities |
KR101281105B1 (ko) * | 2011-01-06 | 2013-07-02 | 한국수력원자력 주식회사 | 수용액 내 존재하는 우라늄 농도의 정량방법 |
JP2012181378A (ja) * | 2011-03-02 | 2012-09-20 | Toyo Ink Sc Holdings Co Ltd | カラーフィルタ用顔料組成物、着色組成物、およびカラーフィルタ |
KR101895047B1 (ko) * | 2011-12-30 | 2018-09-06 | 한미사이언스 주식회사 | 면역글로불린 단편을 이용한 위치 특이적 글루카곤 유사 펩타이드-2 약물 결합체 |
KR102053474B1 (ko) * | 2012-03-06 | 2019-12-06 | 오세-테크놀로지스 베파우 | 잉크 조성물 |
KR101665009B1 (ko) * | 2012-03-09 | 2016-10-11 | 한미사이언스 주식회사 | 비알콜성 지방간 질환의 예방 또는 치료용 약학적 조성물 |
KR20140009641A (ko) * | 2012-07-12 | 2014-01-23 | 서울대학교산학협력단 | 일정한 온도에서 생성된 이온들의 질량 스펙트럼을 측정하는 방법 |
US9646810B2 (en) | 2012-07-17 | 2017-05-09 | Snu R&Db Foundation | Method for improving mass spectrum reproducibility and quantitative analysis method using same |
WO2014107043A1 (ko) | 2013-01-03 | 2014-07-10 | 서울대학교 산학협력단 | 전체 이온 개수를 측정하여 일정한 온도에서 생성된 이온들의 질량 스펙트럼을 구하는 방법 및 말디 질량분석법을 이용한 정량 분석을 위한 매트릭스의 용도 |
US9349578B2 (en) | 2013-01-03 | 2016-05-24 | Asta Co., Ltd. | Quantitative analysis method using mass spectrometry wherein laser pulse energy is adjusted |
GB201310214D0 (en) * | 2013-06-07 | 2013-07-24 | Medical Res Council | Separation and Analysis Systems and Methods |
EP2818859A1 (en) * | 2013-06-28 | 2014-12-31 | Ruprecht-Karls-Universität Heidelberg | Chromatographic Device and Method |
US20150248072A1 (en) * | 2014-02-28 | 2015-09-03 | Canon Kabushiki Kaisha | Toner |
WO2015175685A1 (en) | 2014-05-13 | 2015-11-19 | University Of Houston System | System and method for maldi-tof mass spectrometry |
KR20160009740A (ko) * | 2014-07-16 | 2016-01-27 | 연세대학교 산학협력단 | 말디톱 질량분석기에 이용가능한 시료 플레이트 및 상기 시료 플레이트의 제조방법, 그리고 상기 시료 플레이트를 이용한 질량분석 방법 |
JP6488143B2 (ja) * | 2015-02-13 | 2019-03-20 | 株式会社Dnpファインケミカル | ジケトピロロピロール系顔料誘導体組成物、顔料組成物、顔料分散液、着色樹脂組成物、カラーフィルタ、及び表示装置 |
JP6734505B2 (ja) * | 2015-02-27 | 2020-08-05 | 御国色素株式会社 | 顔料微粒子、顔料分散体、感光性着色組成物及びカラーフィルター |
KR101692314B1 (ko) | 2015-03-27 | 2017-01-03 | 주식회사 주빅 | 지용성 약물의 생분해성 고분자 내 용해 시스템: 스마트 폴리머 시스템 |
KR101761484B1 (ko) | 2015-10-30 | 2017-07-26 | 국방과학연구소 | 말디-질량분석용 유기 매트릭스 용액의 제조 방법 및 이에 의해 제조된 유기 매트릭스 |
KR101811744B1 (ko) | 2016-03-07 | 2017-12-22 | (주)아이투에이시스템즈 | 광센서를 이용한 토크 센서 및 이를 포함하는 토크 측정 장치 |
CN105854715B (zh) | 2016-04-21 | 2019-03-05 | 北京百思声创科技有限公司 | 超声搅拌容器 |
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US11397138B2 (en) | 2022-07-26 |
KR102174436B1 (ko) | 2020-11-04 |
WO2019035521A1 (ko) | 2019-02-21 |
EP3671192A1 (en) | 2020-06-24 |
US20200166437A1 (en) | 2020-05-28 |
EP3671192B1 (en) | 2022-09-21 |
KR20190019436A (ko) | 2019-02-27 |
EP3671192A4 (en) | 2020-07-29 |
JP2020514744A (ja) | 2020-05-21 |
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