Dispersant, metal particle dispersion for electroconductive substrates, and method for producing electroconductive substrate

Patent metadata

Field	Value
Publication number	US-9953740-B2
Application number	US-201314436257-A
Country	US
Kind code	B2
Filing date	Oct 17, 2013
Priority date	Oct 18, 2012
Publication date	Apr 24, 2018
Grant date	Apr 24, 2018

Abstract

The present invention is to provide a dispersant which has excellent dispersibility and which is able to inhibit the oxidation of dispersed particles. Disclosed is a dispersant comprising a graft copolymer having a constitutional unit represented by the following general formula (I) and a constitutional unit represented by the following general formula (II):

(Symbols shown in the general formulae (I) and (II) are as described in the Description.)

First claim

The invention claimed is:

1. A dispersant comprising a graft copolymer comprising a constitutional unit represented by the following general formula (I) and a constitutional unit represented by the following general formula (II):

wherein “A” is a direct bond or a divalent linking group, and the divalent linking group as “A” is at least one selected from the group consisting of a linear, branched or cyclic alkylene group, a linear, branched or cyclic alkylene group comprising a hydroxyl group, an arylene group, a —CONH— group, a —COO— group, a —NHCOO— group, an ether group (—O— group), a thioether group (—S— group) and combinations thereof; R 1 is a hydrogen atom or a methyl group; R 2 is a hydrogen atom, a hydrocarbon group optionally comprising a substituent group, or a monovalent group represented by —[CH(R 4 )—CH(R 5 )—O] s —R 6 , —[(CH 2 ) t —O] u —R 6 or —O—R 7 ; R 7 is a hydrocarbon group optionally comprising a substituent group, or a monovalent group represented by —[CH(R 4 )—CH(R 5 )—O] s —R 6 , —[(CH 2 ) t —O] u —R 6 , —C(R 8 )(R 9 )—C(R 10 )(R 11 )—OH or —CH 2 —C(R 12 )(R 13 )—CH 2 —OH;
R 4 and R 5 are each independently a hydrogen atom or a methyl group; R 6 is a hydrogen atom, a hydrocarbon group optionally comprising a substituent group, or a monovalent group represented by —CHO, —CH 2 CHO, —CO—CH═CH 2 , —CO—C(CH 3 )═CH 2 or —CH 2 COOR 14 ; R 14 is a hydrogen atom or an alkyl group comprising 1 to 5 carbon atoms; R 8 , R 9 , R 10 , R 11 , R 12 and R 13 are each independently a hydrogen atom, a hydrocarbon group optionally comprising a substituent group, or a group in which hydrocarbon groups optionally comprising a substituent group, are bound by at least one of an ether bond and an ester bond, and R 8 and R 10 can be bound to each other to form a cyclic structure; when the cyclic structure is formed, the cyclic structure can comprise a substituent group R 15 , and R 15 is a hydrogen atom, a hydrocarbon group optionally comprising a substituent group, or a group in which hydrocarbon groups optionally comprising a substituent group, are bound by at least one of an ether bond and an ester bond;
the substituent group in R 2 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 and R 15 is at least one selected from the group consisting of a nitro group and a halogen atom, and when R 2 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 and R 15 are each a group comprising an aromatic ring, the aromatic ring can comprise a substituent group of an alkyl or alkenyl group;
s is an integer of 1 to 18; t is an integer of 1 to 5; and u is an integer of 1 to 18;
wherein “L” is a direct bond or a divalent linking group, and the divalent linking group as “L” is at least one selected from the group consisting of a linear, branched or cyclic alkylene group, a linear, branched or cyclic alkylene group comprising a hydroxyl group, an arylene group, a —CONH— group, a —COO— group, a —NHCOO— group, an ether group (—O— group), a thioether group (—S— group) and combinations thereof; R 3 is a hydrogen atom or a methyl group; “Polymer” is a polymer chain comprising at least one constitutional unit represented by the following general formula (III) or (IV):

wherein R 17 is a hydrogen atom or a methyl group; R 18 is a hydrocarbon group optionally comprising a substituent group, a cyano group or a monovalent group represented by —[CH(R 19 )—CH(R 20 )—O] x —R 21 , —[(CH 2 ) y —O] z —R 21 , —[CO—(CH 2 ) y —O] z —R 21 , —CO—O—R 22 or —O—CO—R 23 ; R 19 and R 20 are each independently a hydrogen atom or a methyl group;
R 21 is a hydrogen atom, a hydrocarbon group optionally comprising a substituent group, or a monovalent group represented by —CHO, —CH 2 CHO or —CH 2 COOR 24 ; R 22 is a hydrocarbon group optionally comprising a substituent group, a cyano group or a monovalent group represented by —[CH(R 19 )—CH(R 20 )—O] x —R 21 , —[(CH 2 ) y —O] z —R 21 or —[CO—(CH 2 ) y —O] z —R 21 ; R 23 is an alkyl group comprising 1 to 18 carbon atoms and optionally comprising a substituent group; R 24 is a hydrogen atom or an alkyl group comprising 1 to 5 carbon atoms;
the substituent group in R 18 , R 21 , R 22 and R 23 is at least one selected from the group consisting of a nitro group, a halogen atom, an alkoxy group, a hydroxyl group, a carboxyl group, an amino group, an epoxy group and an isocyanate group, and when R 18 , R 21 , R 22 and R 23 are each a group comprising an aromatic ring, the aromatic ring can comprise a substituent group of an alkyl or alkenyl group;
m is an integer of 1 to 5; n and n′ are each an integer of 5 to 200; x is an integer of 1 to 18; y is an integer of 1 to 5; and z is an integer of 1 to 18.

2. The dispersant according to claim 1 , wherein the graft copolymer further comprises a constitutional unit represented by the following general formula (V):

wherein R 25 is a hydrogen atom or a methyl group, and “Q” is a direct bond or a divalent linking group, and the divalent linking group as “Q” is at least one selected from the group consisting of an alkylene group comprising 1 to 10 carbon atoms, an arylene group, a —CONH— group, a —COO— group, an ether group comprising 1 to 10 carbon atoms (—R′—OR″— wherein R′ and R″ are each independently an alkylene group) and combinations thereof.

3. A metal particle dispersion for electroconductive substrates, comprising metal particles, a dispersant and an organic solvent,
wherein the dispersant is a graft copolymer comprising a constitutional unit represented by the following general formula (I) and a constitutional unit represented by the following general formula (II):

wherein “A” is a direct bond or a divalent linking group, and the divalent linking group as “A” is at least one selected from the group consisting of a linear, branched or cyclic alkylene group, a linear, branched or cyclic alkylene group comprising a hydroxyl group, an arylene group, a —CONH— group, a —COO— group, a —NHCOO— group, an ether group (—O— group), a thioether group (—S— group) and combinations thereof; R 1 is a hydrogen atom or a methyl group; R 2 is a hydrogen atom, a hydrocarbon group optionally comprising a substituent group, or a monovalent group represented by —[CH(R 4 )—CH(R 5 )—O] s —R 6 , —[(CH 2 ) t —O] u —R 6 or —O—R 7 ; R 7 is a hydrocarbon group optionally comprising a substituent group, or a monovalent group represented by —[CH(R 4 )—CH(R 5 )—O] s —R 6 , —[(CH 2 ) t —O] u —R 6 , —C(R 8 )(R 9 )—C(R 10 )(R 11 )—OH or —CH 2 —C(R 12 )(R 13 )—CH 2 —OH;
R 4 and R 5 are each independently a hydrogen atom or a methyl group; R 6 is a hydrogen atom, a hydrocarbon group optionally comprising a substituent group, or a monovalent group represented by —CHO, —CH 2 CHO, —CO—CH═CH 2 , —CO—C(CH 3 )═CH 2 or —CH 2 COOR 14 ; R 14 is a hydrogen atom or an alkyl group comprising 1 to 5 carbon atoms; R 8 , R 9 , R 10 , R 11 , R 12 and R 13 are each independently a hydrogen atom, a hydrocarbon group optionally comprising a substituent group, or a group in which hydrocarbon groups optionally comprising a substituent group, are bound by at least one of an ether bond and an ester bond, and R 8 and R 10 can be bound to each other to form a cyclic structure; when the cyclic structure is formed, the cyclic structure can comprise a substituent group R 15 , and R 15 is a hydrogen atom, a hydrocarbon group optionally comprising a su

Assignees

• Dainippon Printing Co Ltd

Inventors

• Omori Yoshinobu
• Yoshi Naonobu
• Ogura Michihiro
• Murata Tomoki
• Hojo Mikiko

Classifications

• C08F230/02

  containing phosphorus · CPC title

• C08F8/40

  Introducing phosphorus atoms or phosphorus-containing groups · CPC title

• C09D139/06

  Homopolymers or copolymers of N-vinyl-pyrrolidones · CPC title

• H01B1/22 Primary

  the conductive material comprising metals or alloys · CPC title

• C08L39/04

  Homopolymers or copolymers of monomers containing heterocyclic rings having nitrogen as ring member · CPC title