[go: up one dir, main page]

WO2019022151A1 - Procédé pour la production d'un corps composite de fines particules métalliques - Google Patents

Procédé pour la production d'un corps composite de fines particules métalliques Download PDF

Info

Publication number
WO2019022151A1
WO2019022151A1 PCT/JP2018/027933 JP2018027933W WO2019022151A1 WO 2019022151 A1 WO2019022151 A1 WO 2019022151A1 JP 2018027933 W JP2018027933 W JP 2018027933W WO 2019022151 A1 WO2019022151 A1 WO 2019022151A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
metal
metal fine
hyperbranched polymer
formula
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.)
Ceased
Application number
PCT/JP2018/027933
Other languages
English (en)
Japanese (ja)
Inventor
小島　圭介
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Nissan Chemical Corp
Original Assignee
Nissan Chemical Corp
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Nissan Chemical Corp filed Critical Nissan Chemical Corp
Priority to JP2019532839A priority Critical patent/JPWO2019022151A1/ja
Publication of WO2019022151A1 publication Critical patent/WO2019022151A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F112/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
    • C08F112/02—Monomers containing only one unsaturated aliphatic radical
    • C08F112/04—Monomers containing only one unsaturated aliphatic radical containing one ring
    • C08F112/14—Monomers containing only one unsaturated aliphatic radical containing one ring substituted by hetero atoms or groups containing heteroatoms
    • C08F112/26—Nitrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F112/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
    • C08F112/02—Monomers containing only one unsaturated aliphatic radical
    • C08F112/04—Monomers containing only one unsaturated aliphatic radical containing one ring
    • C08F112/14—Monomers containing only one unsaturated aliphatic radical containing one ring substituted by hetero atoms or groups containing heteroatoms
    • C08F112/30—Sulfur
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/02—Elements
    • C08K3/08—Metals
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L25/00—Compositions of, homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Compositions of derivatives of such polymers
    • C08L25/18—Homopolymers or copolymers of aromatic monomers containing elements other than carbon and hydrogen

Definitions

  • a method for producing a metal fine particle composite In the formula [1], X represents a halogen atom, R 1 each independently represents a hydrogen atom or a methyl group, and A 1 represents a compound of the formula [2]: (Wherein, A 2 represents a linear, branched or cyclic alkylene group having 1 to 30 carbon atoms which may contain an ether bond or an ester bond.
  • Examples of the linear alkyl group having 1 to 20 carbon atoms as R 2 to R 4 include methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n -Heptyl group, n-octyl group, n-nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n-hexadecyl group -Heptadecyl group, n-octadecyl group, n-nonadecyl group, n-eicosyl group and the like.
  • Ammonium group terminal (-N + H 2 R, -N + HRR ') in which a secondary amine (secondary amino group: -NHR) and a tertiary amine (tertiary amino group: -NRR') are protonated Hyperbranched polymer is obtained.
  • the terminal secondary amine of the corresponding hyperbranched polymer can be obtained by mixing it with an aqueous solution of an acid such as hydrogen chloride, hydrogen bromide or hydrogen iodide in an organic solvent.
  • an acid such as hydrogen chloride, hydrogen bromide or hydrogen iodide
  • the hyperbranched polymer which has such an ammonium group at the molecular terminal is specifically a hyperbranched polymer represented by the following formula [4].
  • R 1 , R 2 to R 4 , A 1 and n have the same meaning as described above, and X ⁇ represents an anion of a halogen atom (halide ion).
  • the above-mentioned A 1 is a structure represented by the above-mentioned formula [5]
  • X ⁇ is a chloride ion below formula [6]
  • hyperbranched polymers represented by In said Formula [6] R ⁇ 1 >, R ⁇ 2 > -R ⁇ 4 > and n represent the same meaning as the above.
  • metal fine particles are obtained in the form of a fine particle complex.
  • a metal salt is added to the system in the presence of a reducing agent, the metal ion generated from the metal salt in the system is reduced by the action of the reducing agent, and the metal of the hyperbranched polymer and the metal fine particles Metal fine particles are obtained in the form of a fine particle complex.
  • a metal ion source and, if desired, a solvent are added to a reaction system containing a hyperbranched polymer, and the target metal fine particle complex is also reacted by reacting under a hydrogen gas atmosphere. You can get it.
  • metal ion sources used here the above-mentioned metal salts, hexacarbonylchromium [Cr (CO) 6 ], pentacarbonyliron [Fe (CO) 5 ], octacarbonyldicobalt [Co 2 (CO) 8 ] And metal carbonyl complexes such as tetracarbonylnickel [Ni (CO) 4 ] can be used.
  • zero-valent metal complexes such as metal olefin complexes, metal phosphine complexes and metal nitrogen complexes can also be used.
  • the solvent to be used is not particularly limited as long as it can dissolve metal ions (metal ion source) and hyperbranched polymer above the necessary concentration, but specifically, alcohols such as ethanol and propanol; methylene chloride, Halogenated hydrocarbons such as chloroform; cyclic ethers such as tetrahydrofuran, 2-methyltetrahydrofuran and tetrahydropyran; nitriles such as acetonitrile and butyronitrile etc. and mixtures of these solvents, with preference given to tetrahydrofuran .
  • the temperature at which the metal ion source and the hyperbranched polymer are mixed can generally be in the range of 0 ° C. to the boiling point of the solvent.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Manufacture Of Metal Powder And Suspensions Thereof (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

L'invention a pour objet un procédé de production plus efficace pour la production en masse d'un corps composite de fines particules métalliques. A cet effet, l'invention porte sur un procédé pour la production d'un corps composite de fines particules métalliques, qui est caractérisé en ce qu'il comprend : une étape consistant à préparer un polymère hyper-ramifié, qui est représenté par la formule (4) et qui comprend un groupe ammonium à une extrémité, dans un système de réaction ; et une étape consistant à ajouter un sel métallique au système de réaction en présence d'un agent réducteur ou une étape consistant à ajouter directement de fines particules métalliques au système de réaction après l'étape de préparation. (Dans la formule, R1 représente un atome d'hydrogène ou un groupe méthyle ; chacun de R2 à R4 représente un atome d'hydrogène, un groupe alkylène éventuellement substitué, un groupe arylalkyle ou similaire ; ou en variante, deux fractions parmi les fractions R2 à R4 peuvent se combiner l'une avec l'autre pour former un groupe alkylène ou les fractions R2 à R4 peuvent se combiner les unes avec les autres pour former un cycle conjointement avec les atomes d'azote auxquels les fractions R2 à R4 sont liées ; X- représente un ion négatif ; n représente un nombre entier de 5 à 100 000 ; et A1 représente une structure représentée par la formule (2) (dans laquelle A2 représente un groupe alkylène ; et chacun de Y1 à Y4 représente un atome d'hydrogène, un groupe alkyle, un groupe alcoxy ou similaire).)
PCT/JP2018/027933 2017-07-25 2018-07-25 Procédé pour la production d'un corps composite de fines particules métalliques Ceased WO2019022151A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2019532839A JPWO2019022151A1 (ja) 2017-07-25 2018-07-25 金属微粒子複合体の製造方法

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2017143670 2017-07-25
JP2017-143670 2017-07-25

Publications (1)

Publication Number Publication Date
WO2019022151A1 true WO2019022151A1 (fr) 2019-01-31

Family

ID=65040813

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2018/027933 Ceased WO2019022151A1 (fr) 2017-07-25 2018-07-25 Procédé pour la production d'un corps composite de fines particules métalliques

Country Status (3)

Country Link
JP (1) JPWO2019022151A1 (fr)
TW (1) TW201920306A (fr)
WO (1) WO2019022151A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2022551646A (ja) * 2019-11-06 2022-12-12 ヘレウス ドイチェラント ゲーエムベーハー ウント カンパニー カーゲー 白金錯体の調製物

Citations (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010021386A1 (fr) * 2008-08-22 2010-02-25 日産化学工業株式会社 Agent de dispersion de microparticules de métal comprenant un composé polymère ramifié ayant un groupe ammonium
WO2012141216A1 (fr) * 2011-04-12 2012-10-18 国立大学法人九州大学 Primaire pour dépôt autocatalytique comprenant un polymère hyperramifié, des microparticules métalliques et un acide organique
WO2012141215A1 (fr) * 2011-04-12 2012-10-18 日産化学工業株式会社 Primaire pour dépôt autocatalytique comprenant un polymère hyperramifié et des microparticules métalliques
JP2012196666A (ja) * 2011-03-10 2012-10-18 Kyushu Univ 担持された分岐高分子−金属微粒子複合体
WO2013122136A1 (fr) * 2012-02-14 2013-08-22 国立大学法人群馬大学 Microparticules métalliques associées et leur procédé de fabrication
WO2014042215A1 (fr) * 2012-09-13 2014-03-20 日産化学工業株式会社 Agent de base pour dépôt autocatalytique
JP2014159620A (ja) * 2013-02-20 2014-09-04 Nissan Chem Ind Ltd スクリーン印刷用触媒インク
WO2015088008A1 (fr) * 2013-12-13 2015-06-18 日産化学工業株式会社 Encre à catalyseur pour impression à jet d'encre
WO2016017625A1 (fr) * 2014-07-30 2016-02-04 日産化学工業株式会社 Polymère hyper-ramifié, microparticules de métal, et agent de base de dépôt autocatalytique contenant un apprêt de résine
WO2016035897A1 (fr) * 2014-09-05 2016-03-10 日産化学工業株式会社 Agent de sous-couche de placage autocatalytique photosensible
WO2016035896A1 (fr) * 2014-09-05 2016-03-10 日産化学工業株式会社 Couche primaire pour dépôt autocatalytique photodurcissable
JP2016138314A (ja) * 2015-01-27 2016-08-04 国立大学法人福井大学 微細構造へのめっき方法
WO2016158949A1 (fr) * 2015-03-31 2016-10-06 日産化学工業株式会社 Agent de sous-couche de placage autocatalytique photosensible

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS62207237A (ja) * 1986-03-07 1987-09-11 Mitsubishi Paper Mills Ltd β−アルコキシアクロレイン誘導体の製造法
JPH0776574A (ja) * 1993-09-06 1995-03-20 Wako Pure Chem Ind Ltd ジスルフィド化合物の製造法
JP2002145990A (ja) * 2000-11-14 2002-05-22 Mitsui Chemicals Inc 架橋重合体及びその製造方法

Patent Citations (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2015166084A (ja) * 2008-08-22 2015-09-24 日産化学工業株式会社 アンモニウム基を有する分岐高分子化合物からなる金属微粒子分散剤
WO2010021386A1 (fr) * 2008-08-22 2010-02-25 日産化学工業株式会社 Agent de dispersion de microparticules de métal comprenant un composé polymère ramifié ayant un groupe ammonium
JP2012196666A (ja) * 2011-03-10 2012-10-18 Kyushu Univ 担持された分岐高分子−金属微粒子複合体
WO2012141216A1 (fr) * 2011-04-12 2012-10-18 国立大学法人九州大学 Primaire pour dépôt autocatalytique comprenant un polymère hyperramifié, des microparticules métalliques et un acide organique
WO2012141215A1 (fr) * 2011-04-12 2012-10-18 日産化学工業株式会社 Primaire pour dépôt autocatalytique comprenant un polymère hyperramifié et des microparticules métalliques
WO2013122136A1 (fr) * 2012-02-14 2013-08-22 国立大学法人群馬大学 Microparticules métalliques associées et leur procédé de fabrication
WO2014042215A1 (fr) * 2012-09-13 2014-03-20 日産化学工業株式会社 Agent de base pour dépôt autocatalytique
JP2014159620A (ja) * 2013-02-20 2014-09-04 Nissan Chem Ind Ltd スクリーン印刷用触媒インク
WO2015088008A1 (fr) * 2013-12-13 2015-06-18 日産化学工業株式会社 Encre à catalyseur pour impression à jet d'encre
WO2016017625A1 (fr) * 2014-07-30 2016-02-04 日産化学工業株式会社 Polymère hyper-ramifié, microparticules de métal, et agent de base de dépôt autocatalytique contenant un apprêt de résine
WO2016035897A1 (fr) * 2014-09-05 2016-03-10 日産化学工業株式会社 Agent de sous-couche de placage autocatalytique photosensible
WO2016035896A1 (fr) * 2014-09-05 2016-03-10 日産化学工業株式会社 Couche primaire pour dépôt autocatalytique photodurcissable
JP2016138314A (ja) * 2015-01-27 2016-08-04 国立大学法人福井大学 微細構造へのめっき方法
WO2016158949A1 (fr) * 2015-03-31 2016-10-06 日産化学工業株式会社 Agent de sous-couche de placage autocatalytique photosensible

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2022551646A (ja) * 2019-11-06 2022-12-12 ヘレウス ドイチェラント ゲーエムベーハー ウント カンパニー カーゲー 白金錯体の調製物
JP7354435B2 (ja) 2019-11-06 2023-10-02 ヘレウス ドイチェラント ゲーエムベーハー ウント カンパニー カーゲー 白金錯体の調製物

Also Published As

Publication number Publication date
JPWO2019022151A1 (ja) 2020-07-09
TW201920306A (zh) 2019-06-01

Similar Documents

Publication Publication Date Title
TWI548650B (zh) 含有高分支化聚合物及金屬微粒子之無電解鍍敷基劑
US10279393B2 (en) Method of producing copper nano particle colloidal dispersions
JP4520969B2 (ja) 金属ナノ粒子及びその製造方法
JP5991510B2 (ja) 銅ナノワイヤーの製造方法
JP6354950B2 (ja) 無電解めっき下地剤
JP6021804B2 (ja) ハイパーブランチポリマー、金属微粒子及び有機酸を含む無電解めっき下地剤
EP1905756A1 (fr) Beta-cetocarboxylate d'argent, materiau en comportant pour la formation de d'argent metallique, et leur utilisation
KR20140027624A (ko) 상전이 환원법을 이용한 금속 나노입자의 제조방법 및 이로부터 제조된 금속 나노입자를 포함한 금속잉크
JP6571008B2 (ja) 導電性ナノファイバーの製造方法
JP6649609B2 (ja) インクジェット印刷用触媒インク
JP2010064983A (ja) ニッケル粒子の製造方法及びそれに適したニッケル錯体
CN106662812B (zh) 感光性非电解镀基底剂
Fan et al. Pd/Cu bimetallic catalyst immobilized on PEI capped cellulose-polyamidoamine dendrimer: Synthesis, characterization, and application in Sonogashira reactions for the synthesis of alkynes and benzofurans
JP2016138314A (ja) 微細構造へのめっき方法
WO2019022151A1 (fr) Procédé pour la production d'un corps composite de fines particules métalliques
KR101747184B1 (ko) 수용해성을 증가시킨 프탈로시아닌 유도체 및 이의 제조 방법
Yen et al. Synthesis and application of palladium stearates as precursors for the preparation of palladium nanoparticles
JP5555917B2 (ja) 脂肪族第一級アミンのモノメチル化方法
JP2012196666A (ja) 担持された分岐高分子−金属微粒子複合体
CN113663670A (zh) 一种硝基芳烃高选择性还原催化剂及其制备方法和应用
US8597424B2 (en) Composition and method for forming an aluminum film
JP2009137912A (ja) 芳香族アミン化合物の合成方法

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 18839244

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 2019532839

Country of ref document: JP

Kind code of ref document: A

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 18839244

Country of ref document: EP

Kind code of ref document: A1