JP2001153842A - Surface analytic method - Google Patents
Surface analytic methodInfo
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- JP2001153842A JP2001153842A JP33449199A JP33449199A JP2001153842A JP 2001153842 A JP2001153842 A JP 2001153842A JP 33449199 A JP33449199 A JP 33449199A JP 33449199 A JP33449199 A JP 33449199A JP 2001153842 A JP2001153842 A JP 2001153842A
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- sample
- matrix
- solvent
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- matrix solution
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Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、表面分析方法に関
し、詳しくは、マトリックス支援レーザー脱離イオン化
−飛行時間質量分析計（ＭＡＬＤＩ−ＴＯＦ−ＭＳ）に
よる表面分析方法の改良に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a surface analysis method, and more particularly, to an improvement of a surface analysis method using a matrix-assisted laser desorption / ionization-time-of-flight mass spectrometer (MALDI-TOF-MS).
【０００２】[0002]
【従来の技術】飛行時間質量分析計（ＴＯＦ−ＭＳ）
は、イオンを真空の管中で飛行させ、検出器まで到達す
る時間の違いによってイオンをｍ／ｚ値に応じて分離す
る方式の質量分析計であり、マトリックス支援レーザー
脱離イオン化（ＭＡＬＤＩ）は、分析物質が直接にイオ
ン化されて分解する等の問題を回避するため、分析物質
に添加した有機マトリックスをイオン化し、それによっ
て分析物質をイオン化する手法である。斯かるＭＡＬＤ
Ｉ−ＴＯＦ−ＭＳによる分析方法は、生体高分子、オリ
ゴマー、ファインケミカルズ等の分野において、有機化
合物に関する分子量および化学構造情報を得るための手
段として利用されている。2. Description of the Related Art Time-of-flight mass spectrometers (TOF-MS)
Is a mass spectrometer in which ions are flown in a vacuum tube and the ions are separated according to the m / z value according to the difference in time to reach a detector. Matrix-assisted laser desorption ionization (MALDI) is In order to avoid such a problem that the analyte is directly ionized and decomposed, the organic matrix added to the analyte is ionized, thereby ionizing the analyte. Such a mald
The analysis method by I-TOF-MS is used as a means for obtaining molecular weight and chemical structure information on organic compounds in the fields of biopolymers, oligomers, fine chemicals, and the like.
【０００３】ところで、従来より、上記のＭＡＬＤＩ−
ＴＯＦ−ＭＳの特性を活かした表面の微量成分の分析
は、次の様な試料の前処理工程を経て行われている。す
なわち、先ず、適当な溶剤により試料からブリード物質
や汚染物質を洗い出すか又は抽出した後、回収した洗液
または抽出液を濃縮する方法、ブリード物質や汚染物質
を石英ウール等で拭き取るか又はカッター等で掻き取っ
た後、適当な溶媒に溶解する方法などで試料を準備す
る。次いで、適当量採取した試料にマトリックス溶液を
添加混合した後にレーザー照射用ターゲット（ステンレ
ス）に塗布するか、または、ターゲット表面上で夫々を
混合する。そして、溶剤蒸発後にイオン化室に挿入し、
マトリックス塗布面にＮ2レーザー３３７ｎｍを照射し
てＭＡＬＤＩ−ＴＯＦ−ＭＳ分析を行う。By the way, conventionally, the above-mentioned MALDI-
Analysis of trace components on the surface utilizing the characteristics of TOF-MS is performed through the following sample pretreatment process. That is, first, a bleed substance or a contaminant is washed out or extracted from a sample with an appropriate solvent, and then the collected washing liquid or extract is concentrated, and the bleed substance or the contaminant is wiped with quartz wool or a cutter. After that, a sample is prepared by, for example, dissolving in an appropriate solvent. Next, a matrix solution is added to a sample collected in an appropriate amount and mixed, and then applied to a laser irradiation target (stainless steel) or mixed on the target surface. Then, after solvent evaporation, insert it into the ionization chamber,
MALDI-TOF-MS analysis is performed by irradiating a 337 nm N 2 laser to the matrix application surface.
【０００４】しかしながら、上記の前処理工程において
は、煩雑な操作が必要であり、しかも、基材の高分子材
料の溶出や表面にブリードしていない配合成分の溶出、
使用する溶媒、器具、拭き取り材料などからの汚染など
が起こり、分析すべき表面のブリード物質や汚染物質の
定性や定量が正確に行われないという問題がある。[0004] However, in the above-mentioned pretreatment step, complicated operations are required, and moreover, the elution of the polymer material of the base material, the elution of the components not bleeding on the surface,
There is a problem that contamination from a solvent, equipment, a wiping material, or the like to be used occurs, and qualitative or quantitative determination of bleeding substances and contaminants on the surface to be analyzed is not performed accurately.
【０００５】[0005]
【発明が解決しようとする課題】本発明は、上記実情に
鑑みなされたものであり、その目的は、試料の前処理工
程が簡略化され、しかも、各種の表面に付着したブリー
ド物質や汚染物質の分子量および化学構造情報を正確に
得ることが出来る、マトリックス支援レーザー脱離イオ
ン化−飛行時間質量分析計（ＭＡＬＤＩ−ＴＯＦ−Ｍ
Ｓ）による表面分析方法を提供することにある。SUMMARY OF THE INVENTION The present invention has been made in view of the above circumstances, and an object of the present invention is to simplify a sample pretreatment step, and furthermore, to bleed and contaminate substances adhered to various surfaces. -Assisted laser desorption / ionization-time-of-flight mass spectrometer (MALDI-TOF-M) capable of accurately obtaining molecular weight and chemical structure information of
An object of the present invention is to provide a surface analysis method according to S).
【０００６】[0006]
【課題を解決するための手段】すなわち、本発明の要旨
は、マトリックス支援レーザー脱離イオン化−飛行時間
質量分析計による表面分析方法において、試料の表面に
揮発性溶媒のマトリックス溶液を直接塗布し、溶媒を蒸
発させた後、マトリックス溶液塗布面に紫外線レーザー
を照射してイオン化を行って試料表面の化学物質に関連
するマススペクトルを得ることを特徴とする上記の表面
分析方法に存する。That is, the gist of the present invention is to provide a method of surface analysis using matrix-assisted laser desorption / ionization-time-of-flight mass spectrometry, in which a matrix solution of a volatile solvent is directly applied to the surface of a sample, After the solvent is evaporated, the surface analysis method is characterized in that the surface coated with the matrix solution is irradiated with an ultraviolet laser to perform ionization to obtain a mass spectrum related to a chemical substance on the sample surface.
【０００７】[0007]
【発明の実施の形態】以下、本発明を詳細に説明する。
本発明の表面分析方法それ自体は、基本的には、従来の
マトリックス支援レーザー脱離イオン化−飛行時間質量
分析計（ＭＡＬＤＩ−ＴＯＦ−ＭＳ）による表面分析方
法と同じである。BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, the present invention will be described in detail.
The surface analysis method of the present invention itself is basically the same as the surface analysis method using a conventional matrix-assisted laser desorption / ionization-time-of-flight mass spectrometer (MALDI-TOF-MS).
【０００８】本発明の特徴は、試料の前処理工程にあ
る。すなわち、本発明においては、試料の表面に揮発性
溶媒のマトリックス溶液を直接塗布する。好ましい態様
においては、例えば両面テープ等を使用してレーザー照
射用ターゲット表面に試料を貼り付け、当該試料の表面
に揮発性溶媒のマトリックス溶液を直接塗布する。A feature of the present invention resides in a sample pretreatment step. That is, in the present invention, a matrix solution of a volatile solvent is directly applied to the surface of the sample. In a preferred embodiment, the sample is attached to the surface of the target for laser irradiation using, for example, a double-sided tape or the like, and a matrix solution of a volatile solvent is directly applied to the surface of the sample.
【０００９】上記のマトリックス溶液の調製溶媒として
は、試料の貧溶媒または試料を溶解しない溶媒の中から
選択される揮発性溶媒が好適である。試料が合成樹脂ま
たは合成樹脂製品の場合は、上記の溶媒の具体例として
は、テトラヒドロフラン、メチルアルコール等が挙げら
れる。As the solvent for preparing the above matrix solution, a volatile solvent selected from a poor solvent for the sample or a solvent that does not dissolve the sample is suitable. When the sample is a synthetic resin or a synthetic resin product, specific examples of the solvent include tetrahydrofuran and methyl alcohol.
【００１０】上記のマトリックスとしては、紫外線領域
に吸収を有する有機物質が好適である。斯かるマトリッ
クスの具体例としては、例えば、１，４−ビス（５−フ
ェニルオキサゾル−２イル）ベンゼン（分子量３６
４）、１，８，９−トリヒドロキシアントラセン（２２
６）、２，４，６−トリヒドロキシアセトフェノン（１
６８）、２，５−ジヒドロキシ安息香酸（１５４）、２
−（４−ヒドロキシフェニルアゾ）安息香酸（２４
２）、２−アミノ安息香酸（１３７）、３−アミノピラ
ジン−２−カルボン酸（１２３）、３−ヒドロキシピコ
リン酸（１３９）、４−ヒドロキシ−３−メトキシケイ
皮酸（１９４）、トランス−インドールアクリル酸（１
８７）、２，６−ジヒドロキシアセトフェノン（１５
２）、５−メトキシサリチル酸（１６８）、５−クロロ
サリチル酸（１７２．６）、９−アントラセンカルボン
酸（２２２）、インドール酢酸（１７５）、トランス−
３−ジメトキシ−ヒドロキシケイ皮酸（２２４）、α−
シアノ−４−ヒドロキシケイ皮酸（１８９）、１，４−
ジフェニルブタジエン（２０６）、３，４−ジヒドロキ
シケイ皮酸（１８０）等が挙げられる。これらのマトリ
ックスは、好ましくは０．２〜１５重量％の溶液として
使用される。As the matrix, an organic substance having absorption in the ultraviolet region is preferable. Specific examples of such a matrix include, for example, 1,4-bis (5-phenyloxazol-2-yl) benzene (molecular weight 36
4), 1,8,9-trihydroxyanthracene (22
6), 2,4,6-trihydroxyacetophenone (1
68), 2,5-dihydroxybenzoic acid (154), 2
-(4-hydroxyphenylazo) benzoic acid (24
2), 2-aminobenzoic acid (137), 3-aminopyrazine-2-carboxylic acid (123), 3-hydroxypicolinic acid (139), 4-hydroxy-3-methoxycinnamic acid (194), trans- Indole acrylic acid (1
87), 2,6-dihydroxyacetophenone (15
2), 5-methoxysalicylic acid (168), 5-chlorosalicylic acid (172.6), 9-anthracenecarboxylic acid (222), indoleacetic acid (175), trans-
3-dimethoxy-hydroxycinnamic acid (224), α-
Cyano-4-hydroxycinnamic acid (189), 1,4-
Diphenylbutadiene (206), 3,4-dihydroxycinnamic acid (180) and the like. These matrices are preferably used as solutions of 0.2 to 15% by weight.
【００１１】そして、本発明においては、溶媒を蒸発さ
せた後、マトリックス溶液塗布面に紫外線レーザーを照
射してイオン化を行って試料表面の化学物質に関連する
マススペクトルを得る。本発明においては、マトリック
スとして紫外線領域に吸収を有する有機物質を使用した
場合、レーザー源としては、Ｎ2レーザー３３７ｎｍが
好適に使用される。In the present invention, after evaporating the solvent, the surface coated with the matrix solution is irradiated with an ultraviolet laser to perform ionization to obtain a mass spectrum related to a chemical substance on the sample surface. In the present invention, when an organic substance having absorption in the ultraviolet region is used as the matrix, an N 2 laser of 337 nm is suitably used as a laser source.
【００１２】本発明の表面分析は、各種物質の表面に存
在する化学物質の分析に広く使用することが出来るが、
特に、合成樹脂または合成樹脂製品の表面のブリード物
質または汚染物質に関する分子量および化学構造の情報
を得るための手段として有用である。The surface analysis of the present invention can be widely used for analyzing chemical substances existing on the surface of various substances.
In particular, it is useful as a means for obtaining information on the molecular weight and chemical structure of bleeding substances or contaminants on the surface of a synthetic resin or a synthetic resin product.
【００１３】[0013]
【実施例】以下、本発明を実施例により更に詳細に説明
するが、本発明は、その要旨を超えない限り、以下の実
施例に限定されるものではない。以下、諸例において
は、ＭＡＬＤＩ−ＴＯＦ−ＭＳ計としてＮ2レーザー３
３７ｎｍ装着「Ｆｉｎｎｉｇａｎ Ｍａｔ Ｖｉｓｉｏ
ｎ ２０００」（サーモクエスト社製）を使用した。EXAMPLES Hereinafter, the present invention will be described in more detail with reference to examples, but the present invention is not limited to the following examples unless it exceeds the gist of the present invention. Hereinafter, in various examples, a N 2 laser 3 was used as a MALDI-TOF-MS meter.
37nm wearing "Finnigan Mat Visio"
n 2000 "(manufactured by ThermoQuest).
【００１４】比較例１ 樹脂添加剤としてリン系酸化防止剤「ＰＥＰＱ」と光安
定剤「Ｃｈｉｍａｓｓｏｒｂ９４４ＬＤ」が配合された
厚さ２０μmのＬ−ＬＤＰＥ（直鎖低密度ポリエチレ
ン）フィルム１ｇにクロロホルム３０mｌを加え２時間
還流し、クロロホルム抽出液を得た。COMPARATIVE EXAMPLE 1 30 ml of chloroform was added to 1 g of an L-LDPE (linear low-density polyethylene) film having a thickness of 20 μm containing a phosphorus-based antioxidant “PEPQ” and a light stabilizer “Chimassorb 944LD” as resin additives. The mixture was refluxed for 2 hours to obtain a chloroform extract.
【００１５】冷却後、濾紙（東洋濾紙Ｎｏ４）で抽出液
中のフィルムを除去し、得られた濾液を約１mｌまで濃
縮した。マトリックスとしてトリヒドロキシアセトフェ
ノン（ＴＨＡＰ）を８０mｇ／mｌ濃度で含むテトラヒド
ロフラン（ＴＨＦ）溶液を準備し、このマトリックス溶
液１００μｌと上記の濃縮液１００μｌをよく混合し、
レーザー照射用ターゲットに１μｌ塗布し、自然乾燥
後、イオン化室に挿入し、ＭＡＬＤＩ−ＴＯＦ−ＭＳス
ペクトルを測定した。その結果、リン系酸化防止剤「Ｐ
ＥＰＱ」と光安定剤「９４４ＬＤ」が顕著に検出され
た。After cooling, the film in the extract was removed with filter paper (Toyo Filter Paper No. 4), and the obtained filtrate was concentrated to about 1 ml. A tetrahydrofuran (THF) solution containing trihydroxyacetophenone (THAP) at a concentration of 80 mg / ml is prepared as a matrix, and 100 μl of the matrix solution and 100 μl of the above concentrated solution are mixed well,
1 μl of the solution was applied to a target for laser irradiation, dried naturally, inserted into an ionization chamber, and the MALDI-TOF-MS spectrum was measured. As a result, the phosphorus-based antioxidant “P
EPQ "and the light stabilizer" 944LD "were remarkably detected.
【００１６】実施例１ ０．１０mmの厚さ表面研磨したレーザー照射用ターゲッ
トの表面に両面テープを貼り、その上に比較例１と同様
のフィルムを貼り付け、当該フィルムの表面にＴＨＡＰ
を４０mｇ／mｌ濃度で含むメチルアルコール溶液を直接
１μｌ塗布し、自然乾燥後、イオン化室に挿入し、ＭＡ
ＬＤＩ−ＴＯＦ−ＭＳスペクトルを測定した。その結
果、「ＰＥＰＱ」は殆ど検出されず、「９４４ＬＤ」の
低分子量体（＜４０００）が検出された。これは、L−
ＬＤＰＥフィルムの表面は「ＰＥＰＱ」に比し「９４４
ＬＤ」のブリードが激しいことを示している。また、
「９４４ＬＤ」の低分子量体ほど表面にブリードし易い
傾向があるこも示唆している。Example 1 A double-sided tape was stuck on the surface of a laser irradiation target having a thickness of 0.10 mm, and the same film as in Comparative Example 1 was stuck thereon, and THAP was stuck on the surface of the film.
Was directly applied to a 1 μl methyl alcohol solution containing 40 mg / ml, and after air-drying, was inserted into an ionization chamber.
The LDI-TOF-MS spectrum was measured. As a result, "PEPQ" was hardly detected, and a low molecular weight compound (<4000) of "944LD" was detected. This is L-
The surface of the LDPE film is “944” in comparison with “PEPQ”.
LD "bleed. Also,
It also suggests that the lower molecular weight of “944LD” tends to bleed on the surface.
【００１７】実施例２ 実施例１において、ＴＨＡＰ溶液の調製にＴＨＦを使用
した以外は、実施例１と同様にしてＭＡＬＤＩ−ＴＯＦ
−ＭＳスペクトルを測定した。実施例１と同様のマスス
ペクトルが得られ、Ｌ−ＬＤＰＥフィルム表面に「９４
４ＬＤ」の低分子量体がブリードしていることが確認さ
れた。Example 2 A MALDI-TOF was prepared in the same manner as in Example 1 except that THF was used to prepare a THAP solution.
-The MS spectrum was measured. A mass spectrum similar to that of Example 1 was obtained, and "94" was added to the surface of the L-LDPE film.
It was confirmed that the low molecular weight substance of "4LD" was bleeding.
【００１８】実施例３ 実施例１と同様にしてレーザー照射用ターゲットの表面
の両面テープの上にブリードを起こした厚さ１４μｍの
フィルムを貼り付け、その表面にＴＨＡＰを４０mｇ／m
ｌ濃度で含むＴＨＦを直接１μｌ塗布し、自然乾燥後、
イオン化室に挿入し、ＭＡＬＤＩ−ＴＯＦ−ＭＳスペク
トルを測定した。その結果、フィルムの表面からチッソ
系帯電防止剤および質量４４が増加した成分（即ちチッ
ソ系帯電防止剤の酸化エチレン付加体）とリン系酸化防
止剤がブリードしていることが確認された。Example 3 In the same manner as in Example 1, a bleed 14 μm thick film was stuck on the double-sided tape on the surface of the laser irradiation target, and THAP was applied to the surface at a rate of 40 mg / m 2.
1 μl of THF containing 1 l concentration is applied directly, and after natural drying,
It inserted in the ionization room, and measured the MALDI-TOF-MS spectrum. As a result, it was confirmed that the nitrogen-based antistatic agent and the component having an increased mass 44 (ie, the ethylene oxide adduct of the nitrogen-based antistatic agent) and the phosphorus-based antioxidant bleed from the surface of the film.
【００１９】実施例４ 実施例１と同様にしてレーザー照射用ターゲットの表面
の両面テープの上にブリードのない厚さ１４μmのフィ
ルムを貼り付け、その表面にＴＨＡＰを４０mｇ／mｌ濃
度で含むＴＨFを直接１μｌ塗布し、自然乾燥後、イオ
ン化室に挿入し、ＭＡＬＤＩ−ＴＯＦ−ＭＳスペクトル
を測定した。その結果、フィルムの表面にはチッソ系帯
電防止剤とリン系酸化防止剤がブリードしているが、実
施例３のフイルムで顕著に検出されたチッソ系帯電防止
剤の酸化エチレン付加体は殆どブリードしていないこと
が確認された。Example 4 In the same manner as in Example 1, a 14 μm-thick bleed-free film was stuck on a double-sided tape on the surface of a laser irradiation target, and THF containing THAP at a concentration of 40 mg / ml was applied to the surface. 1 μl of the solution was directly applied, dried naturally, inserted into an ionization chamber, and the MALDI-TOF-MS spectrum was measured. As a result, the nitrogen-based antistatic agent and the phosphorus-based antioxidant bleed on the surface of the film, but the ethylene oxide adduct of the nitrogen-based antistatic agent, which was remarkably detected in the film of Example 3, almost did bleed. It was confirmed that it did not.
【００２０】[0020]
【発明の効果】以上説明した本発明によれば、試料の前
処理工程が簡略化され、しかも、各種の表面に付着した
ブリード物質や汚染物質の分子量および化学構造情報を
正確に得ることが出来る、ＭＡＬＤＩ−ＴＯＦ−ＭＳに
よる表面分析方法が提供される。According to the present invention described above, the sample pretreatment step can be simplified, and the molecular weight and chemical structure information of bleeding substances and contaminants adhering to various surfaces can be obtained accurately. , MALDI-TOF-MS is provided.
Claims (5)
−飛行時間質量分析計による表面分析方法において、試
料の表面に揮発性溶媒のマトリックス溶液を直接塗布
し、溶媒を蒸発させた後、マトリックス溶液塗布面に紫
外線レーザーを照射してイオン化を行って試料表面の化
学物質に関連するマススペクトルを得ることを特徴とす
る上記の表面分析方法。In a surface analysis method using matrix-assisted laser desorption / ionization-time-of-flight mass spectrometry, a matrix solution of a volatile solvent is directly applied to the surface of a sample, and after the solvent is evaporated, the sample is applied to the surface to which the matrix solution is applied. The surface analysis method as described above, wherein a mass spectrum related to the chemical substance on the sample surface is obtained by irradiating the sample with an ultraviolet laser to perform ionization.
貼り付け、当該試料の表面に揮発性溶媒のマトリックス
溶液を直接塗布し、溶媒を蒸発させた後、マトリックス
溶液塗布面に紫外線レーザーを照射する請求項１に記載
の方法。2. A method in which a sample is attached to a surface of a target for laser irradiation, a matrix solution of a volatile solvent is directly applied to the surface of the sample, and after evaporating the solvent, an ultraviolet laser is applied to a surface to which the matrix solution is applied. Item 1. The method according to Item 1.
溶媒または試料を溶解しない溶媒の中から選択される揮
発性溶媒である請求項１又は２に記載の方法。3. The method according to claim 1, wherein the solvent dissolving the matrix is a volatile solvent selected from a poor solvent for the sample and a solvent that does not dissolve the sample.
る有機物質であり、レーザー源がＮ2レーザー３３７ｎ
ｍである請求項１〜３の何れかに記載の方法。4. The matrix is an organic substance having absorption in the ultraviolet region, and the laser source is an N 2 laser 337n.
The method according to claim 1, wherein m is m.
成樹脂製品の表面のブリード物質または汚染物質である
請求項１〜４の何れかに記載の方法。5. The method according to claim 1, wherein the chemical substance on the surface of the sample is a bleed substance or a contaminant on the surface of a synthetic resin or a synthetic resin product.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP33449199A JP2001153842A (en) | 1999-11-25 | 1999-11-25 | Surface analytic method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP33449199A JP2001153842A (en) | 1999-11-25 | 1999-11-25 | Surface analytic method |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2001153842A true JP2001153842A (en) | 2001-06-08 |
Family
ID=18278008
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP33449199A Withdrawn JP2001153842A (en) | 1999-11-25 | 1999-11-25 | Surface analytic method |
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| Country | Link |
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| JP (1) | JP2001153842A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004097395A1 (en) * | 2003-04-30 | 2004-11-11 | Sumitomo Chemical Company, Limited | Matrix for matrix aided laser desorption ionization mass analysis |
| US11094517B2 (en) | 2019-03-20 | 2021-08-17 | Ricoh Company, Ltd. | Method and device for preparing measurement sample for MALDI mass spectrometry, measurement sample for MALDI mass spectrometry, MALDI mass spectrometry method, and non-transitory recording medium for preparing measurement sample for MALDI mass spectrometry |
| CN113447561A (en) * | 2021-08-06 | 2021-09-28 | 河北省食品检验研究院 | MALDI-TOF detection method for sheep-derived components in milk powder |
| US11404261B2 (en) | 2020-03-23 | 2022-08-02 | Ricoh Company, Ltd. | Method, device, and base for preparing measurement sample for MALDI mass spectrometry |
| US11532472B2 (en) | 2020-07-30 | 2022-12-20 | Ricoh Company, Ltd. | Mass spectrometry |
-
1999
- 1999-11-25 JP JP33449199A patent/JP2001153842A/en not_active Withdrawn
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004097395A1 (en) * | 2003-04-30 | 2004-11-11 | Sumitomo Chemical Company, Limited | Matrix for matrix aided laser desorption ionization mass analysis |
| US11094517B2 (en) | 2019-03-20 | 2021-08-17 | Ricoh Company, Ltd. | Method and device for preparing measurement sample for MALDI mass spectrometry, measurement sample for MALDI mass spectrometry, MALDI mass spectrometry method, and non-transitory recording medium for preparing measurement sample for MALDI mass spectrometry |
| US11404261B2 (en) | 2020-03-23 | 2022-08-02 | Ricoh Company, Ltd. | Method, device, and base for preparing measurement sample for MALDI mass spectrometry |
| US11532472B2 (en) | 2020-07-30 | 2022-12-20 | Ricoh Company, Ltd. | Mass spectrometry |
| CN113447561A (en) * | 2021-08-06 | 2021-09-28 | 河北省食品检验研究院 | MALDI-TOF detection method for sheep-derived components in milk powder |
| CN113447561B (en) * | 2021-08-06 | 2022-10-14 | 河北省食品检验研究院 | MALDI-TOF detection method for sheep-derived components in milk powder |
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